# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Jay Siegel' _publ_contact_author_email JSS@OCI.UZH.CH _publ_section_title ; Diels-Alder reactions of 3,6-disubstituted 1,2,4,5-tetrazines. Synthesis and X-ray crystal structures of diazafluoranthene derivatives ; loop_ _publ_author_name 'Jay Siegel' 'Kim K Baldridge' 'Anthony Linden' 'Nelli Rahanyan' # Attachment ',6-dimethyl-7,10-bis(methylthio)-8,9-diazafluorant.cif' data_SG0733 _database_code_depnum_ccdc_archive 'CCDC 710120' _audit_creation_method SHELXL-97 _audit_creation_date 07-09-24 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C18 H16 N2 S2' _chemical_formula_sum 'C18 H16 N2 S2' _chemical_formula_weight 324.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 36 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 32 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 4 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; S S 4 0.1246 0.1234 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5950(1) _cell_length_b 10.1858(2) _cell_length_c 10.5743(2) _cell_angle_alpha 105.9648(11) _cell_angle_beta 105.3063(12) _cell_angle_gamma 95.0213(9) _cell_volume 747.19(2) _cell_formula_units_Z 2 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 53689 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.353 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_absorpt_correction_T_min 0.776 _exptl_absorpt_correction_T_max 0.987 _exptl_special_details ; Solvent used: dichloromethane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.682(1) Frames collected: 1288 Seconds exposure per frame: 72 Degrees rotation per frame: 0.6 Crystal-Detector distance (mm): 30.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 21179 _diffrn_reflns_av_R_equivalents 0.0699 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 30.00 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_total 4352 _reflns_number_gt 3454 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0845P)^2^+0.5561P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4352 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1515 _refine_ls_wR_factor_gt 0.1402 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.582 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.111 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.13299(8) 0.23598(5) -0.36295(5) 0.02177(15) Uani 1 1 d . . . S2 S 0.32927(9) 0.43289(5) 0.27429(5) 0.02325(16) Uani 1 1 d . . . N1 N 0.2608(3) 0.45661(18) 0.02555(18) 0.0211(4) Uani 1 1 d . . . N2 N 0.2179(3) 0.41554(18) -0.11306(18) 0.0212(4) Uani 1 1 d . . . C3 C 0.2146(3) 0.28384(19) -0.18214(19) 0.0152(4) Uani 1 1 d . . . C4 C 0.2525(3) 0.18238(19) -0.11462(19) 0.0126(3) Uani 1 1 d . . . C5 C 0.2677(3) 0.03459(19) -0.16153(19) 0.0130(3) Uani 1 1 d . . . C6 C 0.3014(3) -0.0557(2) -0.27531(19) 0.0151(4) Uani 1 1 d . . . C7 C 0.3024(3) -0.1960(2) -0.2780(2) 0.0182(4) Uani 1 1 d . . . H7 H 0.3211 -0.2591 -0.3562 0.022 Uiso 1 1 calc R . . C8 C 0.2781(3) -0.2459(2) -0.1745(2) 0.0186(4) Uani 1 1 d . . . H8 H 0.2770 -0.3413 -0.1831 0.022 Uiso 1 1 calc R . . C9 C 0.2547(3) -0.15410(19) -0.0552(2) 0.0157(4) Uani 1 1 d . . . C10 C 0.2316(3) -0.1899(2) 0.0601(2) 0.0189(4) Uani 1 1 d . . . H10 H 0.2301 -0.2827 0.0620 0.023 Uiso 1 1 calc R . . C11 C 0.2112(3) -0.0889(2) 0.1694(2) 0.0178(4) Uani 1 1 d . . . H11 H 0.1923 -0.1154 0.2448 0.021 Uiso 1 1 calc R . . C12 C 0.2167(3) 0.0531(2) 0.17664(19) 0.0147(4) Uani 1 1 d . . . C13 C 0.2452(3) 0.09106(19) 0.06555(18) 0.0125(3) Uani 1 1 d . . . C14 C 0.2556(3) 0.21947(19) 0.02537(19) 0.0129(3) Uani 1 1 d . . . C15 C 0.2730(3) 0.3635(2) 0.09311(19) 0.0163(4) Uani 1 1 d . . . C16 C 0.2567(3) -0.01526(19) -0.05019(18) 0.0129(3) Uani 1 1 d . . . C17 C 0.1085(4) 0.3989(2) -0.3950(2) 0.0258(5) Uani 1 1 d . . . H171 H 0.0289 0.4455 -0.3444 0.039 Uiso 1 1 calc R . . H172 H 0.0526 0.3824 -0.4940 0.039 Uiso 1 1 calc R . . H173 H 0.2307 0.4574 -0.3642 0.039 Uiso 1 1 calc R . . C18 C 0.3461(3) -0.0177(2) -0.3924(2) 0.0202(4) Uani 1 1 d . . . H181 H 0.2313 -0.0299 -0.4669 0.030 Uiso 1 1 calc R . . H182 H 0.4284 -0.0776 -0.4268 0.030 Uiso 1 1 calc R . . H183 H 0.4077 0.0793 -0.3598 0.030 Uiso 1 1 calc R . . C19 C 0.1858(3) 0.1473(2) 0.3025(2) 0.0200(4) Uani 1 1 d . . . H191 H 0.3050 0.2010 0.3661 0.030 Uiso 1 1 calc R . . H192 H 0.1282 0.0919 0.3480 0.030 Uiso 1 1 calc R . . H193 H 0.1042 0.2107 0.2755 0.030 Uiso 1 1 calc R . . C20 C 0.3475(4) 0.6154(2) 0.2978(2) 0.0316(6) Uani 1 1 d . . . H201 H 0.4332 0.6428 0.2510 0.047 Uiso 1 1 calc R . . H202 H 0.3941 0.6668 0.3965 0.047 Uiso 1 1 calc R . . H203 H 0.2251 0.6363 0.2587 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0363(3) 0.0155(2) 0.0120(2) 0.00498(18) 0.0036(2) 0.0056(2) S2 0.0412(3) 0.0136(2) 0.0129(2) 0.00171(18) 0.0066(2) 0.0065(2) N1 0.0336(10) 0.0137(8) 0.0159(8) 0.0043(6) 0.0067(7) 0.0063(7) N2 0.0347(10) 0.0132(8) 0.0164(8) 0.0055(6) 0.0072(7) 0.0060(7) C3 0.0201(9) 0.0124(8) 0.0131(8) 0.0046(7) 0.0044(7) 0.0024(7) C4 0.0146(9) 0.0112(8) 0.0124(8) 0.0040(6) 0.0044(7) 0.0015(6) C5 0.0125(8) 0.0124(8) 0.0137(8) 0.0038(7) 0.0035(7) 0.0027(6) C6 0.0139(9) 0.0154(9) 0.0145(8) 0.0032(7) 0.0036(7) 0.0026(7) C7 0.0203(10) 0.0138(9) 0.0185(9) 0.0007(7) 0.0067(8) 0.0046(7) C8 0.0192(10) 0.0108(8) 0.0241(10) 0.0044(7) 0.0044(8) 0.0034(7) C9 0.0151(9) 0.0130(8) 0.0183(9) 0.0057(7) 0.0028(7) 0.0027(7) C10 0.0210(10) 0.0143(9) 0.0221(10) 0.0088(7) 0.0046(8) 0.0019(7) C11 0.0186(10) 0.0193(9) 0.0171(9) 0.0098(7) 0.0048(7) 0.0010(7) C12 0.0127(9) 0.0174(9) 0.0130(8) 0.0054(7) 0.0021(7) 0.0010(7) C13 0.0119(8) 0.0121(8) 0.0133(8) 0.0037(6) 0.0036(6) 0.0023(6) C14 0.0152(9) 0.0106(8) 0.0127(8) 0.0040(6) 0.0033(7) 0.0025(6) C15 0.0210(10) 0.0123(8) 0.0136(8) 0.0014(7) 0.0046(7) 0.0031(7) C16 0.0139(9) 0.0114(8) 0.0126(8) 0.0026(6) 0.0039(7) 0.0016(7) C17 0.0407(13) 0.0206(10) 0.0174(10) 0.0100(8) 0.0055(9) 0.0087(9) C18 0.0245(10) 0.0230(10) 0.0164(9) 0.0059(8) 0.0106(8) 0.0078(8) C19 0.0262(11) 0.0203(9) 0.0140(9) 0.0046(7) 0.0075(8) 0.0031(8) C20 0.0576(17) 0.0115(9) 0.0236(11) -0.0007(8) 0.0160(11) 0.0039(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C3 1.7567(19) . ? S1 C17 1.798(2) . ? S2 C15 1.7671(19) . ? S2 C20 1.795(2) . ? N1 C15 1.331(3) . ? N1 N2 1.348(2) . ? N2 C3 1.334(2) . ? C3 C4 1.418(3) . ? C4 C14 1.417(3) . ? C4 C5 1.475(2) . ? C5 C6 1.398(3) . ? C5 C16 1.423(3) . ? C6 C7 1.422(3) . ? C6 C18 1.503(3) . ? C7 C8 1.373(3) . ? C7 H7 0.9500 . ? C8 C9 1.412(3) . ? C8 H8 0.9500 . ? C9 C16 1.399(3) . ? C9 C10 1.414(3) . ? C10 C11 1.373(3) . ? C10 H10 0.9500 . ? C11 C12 1.423(3) . ? C11 H11 0.9500 . ? C12 C13 1.395(3) . ? C12 C19 1.499(3) . ? C13 C16 1.422(2) . ? C13 C14 1.484(3) . ? C14 C15 1.421(2) . ? C17 H171 0.9800 . ? C17 H172 0.9800 . ? C17 H173 0.9800 . ? C18 H181 0.9800 . ? C18 H182 0.9800 . ? C18 H183 0.9800 . ? C19 H191 0.9800 . ? C19 H192 0.9800 . ? C19 H193 0.9800 . ? C20 H201 0.9800 . ? C20 H202 0.9800 . ? C20 H203 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 S1 C17 103.08(10) . . ? C15 S2 C20 101.75(10) . . ? C15 N1 N2 120.37(17) . . ? C3 N2 N1 120.17(17) . . ? N2 C3 C4 122.11(17) . . ? N2 C3 S1 116.81(14) . . ? C4 C3 S1 120.63(14) . . ? C14 C4 C3 116.49(16) . . ? C14 C4 C5 108.95(15) . . ? C3 C4 C5 134.04(17) . . ? C6 C5 C16 118.30(17) . . ? C6 C5 C4 136.69(17) . . ? C16 C5 C4 104.80(15) . . ? C5 C6 C7 117.15(17) . . ? C5 C6 C18 126.35(18) . . ? C7 C6 C18 116.43(17) . . ? C8 C7 C6 124.04(18) . . ? C8 C7 H7 118.0 . . ? C6 C7 H7 118.0 . . ? C7 C8 C9 119.43(18) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C16 C9 C8 117.11(18) . . ? C16 C9 C10 117.15(18) . . ? C8 C9 C10 125.73(18) . . ? C11 C10 C9 119.15(18) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 124.11(18) . . ? C10 C11 H11 117.9 . . ? C12 C11 H11 117.9 . . ? C13 C12 C11 117.49(17) . . ? C13 C12 C19 126.13(18) . . ? C11 C12 C19 116.36(17) . . ? C12 C13 C16 118.05(17) . . ? C12 C13 C14 136.88(17) . . ? C16 C13 C14 104.90(15) . . ? C4 C14 C15 116.00(16) . . ? C4 C14 C13 108.15(15) . . ? C15 C14 C13 135.81(17) . . ? N1 C15 C14 122.34(17) . . ? N1 C15 S2 115.17(14) . . ? C14 C15 S2 122.33(15) . . ? C9 C16 C13 123.89(17) . . ? C9 C16 C5 123.53(17) . . ? C13 C16 C5 112.58(16) . . ? S1 C17 H171 109.5 . . ? S1 C17 H172 109.5 . . ? H171 C17 H172 109.5 . . ? S1 C17 H173 109.5 . . ? H171 C17 H173 109.5 . . ? H172 C17 H173 109.5 . . ? C6 C18 H181 109.5 . . ? C6 C18 H182 109.5 . . ? H181 C18 H182 109.5 . . ? C6 C18 H183 109.5 . . ? H181 C18 H183 109.5 . . ? H182 C18 H183 109.5 . . ? C12 C19 H191 109.5 . . ? C12 C19 H192 109.5 . . ? H191 C19 H192 109.5 . . ? C12 C19 H193 109.5 . . ? H191 C19 H193 109.5 . . ? H192 C19 H193 109.5 . . ? S2 C20 H201 109.5 . . ? S2 C20 H202 109.5 . . ? H201 C20 H202 109.5 . . ? S2 C20 H203 109.5 . . ? H201 C20 H203 109.5 . . ? H202 C20 H203 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N1 N2 C3 -10.1(3) . . . . ? N1 N2 C3 C4 1.0(3) . . . . ? N1 N2 C3 S1 173.30(16) . . . . ? C17 S1 C3 N2 7.7(2) . . . . ? C17 S1 C3 C4 -179.85(17) . . . . ? N2 C3 C4 C14 12.9(3) . . . . ? S1 C3 C4 C14 -159.15(15) . . . . ? N2 C3 C4 C5 -176.5(2) . . . . ? S1 C3 C4 C5 11.5(3) . . . . ? C14 C4 C5 C6 -167.5(2) . . . . ? C3 C4 C5 C6 21.4(4) . . . . ? C14 C4 C5 C16 6.9(2) . . . . ? C3 C4 C5 C16 -164.2(2) . . . . ? C16 C5 C6 C7 6.6(3) . . . . ? C4 C5 C6 C7 -179.6(2) . . . . ? C16 C5 C6 C18 -170.16(18) . . . . ? C4 C5 C6 C18 3.6(4) . . . . ? C5 C6 C7 C8 -2.1(3) . . . . ? C18 C6 C7 C8 175.05(19) . . . . ? C6 C7 C8 C9 -1.6(3) . . . . ? C7 C8 C9 C16 0.4(3) . . . . ? C7 C8 C9 C10 -178.9(2) . . . . ? C16 C9 C10 C11 0.4(3) . . . . ? C8 C9 C10 C11 179.68(19) . . . . ? C9 C10 C11 C12 -1.7(3) . . . . ? C10 C11 C12 C13 -0.2(3) . . . . ? C10 C11 C12 C19 178.18(19) . . . . ? C11 C12 C13 C16 3.4(3) . . . . ? C19 C12 C13 C16 -174.87(18) . . . . ? C11 C12 C13 C14 177.8(2) . . . . ? C19 C12 C13 C14 -0.4(4) . . . . ? C3 C4 C14 C15 -17.1(3) . . . . ? C5 C4 C14 C15 169.99(16) . . . . ? C3 C4 C14 C13 164.66(17) . . . . ? C5 C4 C14 C13 -8.2(2) . . . . ? C12 C13 C14 C4 -168.8(2) . . . . ? C16 C13 C14 C4 6.2(2) . . . . ? C12 C13 C14 C15 13.6(4) . . . . ? C16 C13 C14 C15 -171.5(2) . . . . ? N2 N1 C15 C14 4.8(3) . . . . ? N2 N1 C15 S2 -179.71(16) . . . . ? C4 C14 C15 N1 9.1(3) . . . . ? C13 C14 C15 N1 -173.3(2) . . . . ? C4 C14 C15 S2 -166.04(15) . . . . ? C13 C14 C15 S2 11.5(3) . . . . ? C20 S2 C15 N1 0.5(2) . . . . ? C20 S2 C15 C14 175.98(18) . . . . ? C8 C9 C16 C13 -176.41(18) . . . . ? C10 C9 C16 C13 2.9(3) . . . . ? C8 C9 C16 C5 4.5(3) . . . . ? C10 C9 C16 C5 -176.11(18) . . . . ? C12 C13 C16 C9 -4.9(3) . . . . ? C14 C13 C16 C9 179.02(18) . . . . ? C12 C13 C16 C5 174.24(17) . . . . ? C14 C13 C16 C5 -1.8(2) . . . . ? C6 C5 C16 C9 -8.2(3) . . . . ? C4 C5 C16 C9 176.16(18) . . . . ? C6 C5 C16 C13 172.63(17) . . . . ? C4 C5 C16 C13 -3.0(2) . . . . ? # End of CIF ============================================================ # Attachment 'SG0519.cif' data_SG0519 _database_code_depnum_ccdc_archive 'CCDC 710121' _audit_creation_method SHELXL-97 _audit_creation_date 08-11-07 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C18 H16 N2, 0.5(C2 H3 N)' _chemical_formula_sum 'C19 H17.5 N2.5' _chemical_formula_weight 280.86 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 608 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 560 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 80 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'F d d d ' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 70 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/4, -z+1/4' '-x+1/4, y, -z+1/4' '-x+1/4, -y+1/4, z' 'x, y+1/2, z+1/2' 'x, -y+3/4, -z+3/4' '-x+1/4, y+1/2, -z+3/4' '-x+1/4, -y+3/4, z+1/2' 'x+1/2, y, z+1/2' 'x+1/2, -y+1/4, -z+3/4' '-x+3/4, y, -z+3/4' '-x+3/4, -y+1/4, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+3/4, -z+1/4' '-x+3/4, y+1/2, -z+1/4' '-x+3/4, -y+3/4, z' '-x, -y, -z' '-x, y-1/4, z-1/4' 'x-1/4, -y, z-1/4' 'x-1/4, y-1/4, -z' '-x, -y+1/2, -z+1/2' '-x, y+1/4, z+1/4' 'x-1/4, -y+1/2, z+1/4' 'x-1/4, y+1/4, -z+1/2' '-x+1/2, -y, -z+1/2' '-x+1/2, y-1/4, z+1/4' 'x+1/4, -y, z+1/4' 'x+1/4, y-1/4, -z+1/2' '-x+1/2, -y+1/2, -z' '-x+1/2, y+1/4, z-1/4' 'x+1/4, -y+1/2, z-1/4' 'x+1/4, y+1/4, -z' _cell_length_a 13.9453(4) _cell_length_b 25.7283(5) _cell_length_c 31.5668(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 11325.8(5) _cell_formula_units_Z 32 _cell_measurement_temperature 260(1) _cell_measurement_reflns_used 2727 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4768 _exptl_absorpt_coefficient_mu 0.0786 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: hexane / MeCN Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.379(1) Frames collected: 383 Seconds exposure per frame: 60 Degrees rotation per frame: 1.0 Crystal-Detector distance (mm): 30.0 ; _diffrn_ambient_temperature 260(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 36810 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 2505 _reflns_number_gt 1612 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0878P)^2^+8.1135P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0010(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2503 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0886 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1748 _refine_ls_wR_factor_gt 0.1472 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.233 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.040 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.25062(13) 0.19242(8) 0.83959(7) 0.0754(6) Uani 1 1 d . . . N2 N 0.24728(12) 0.15528(9) 0.81037(7) 0.0741(6) Uani 1 1 d . . . C3 C 0.24461(14) 0.10534(9) 0.82118(7) 0.0609(6) Uani 1 1 d . . . C4 C 0.24684(12) 0.09022(7) 0.86411(6) 0.0492(5) Uani 1 1 d . . . C5 C 0.24549(13) 0.03914(7) 0.88560(6) 0.0533(6) Uani 1 1 d . . . C6 C 0.24061(18) -0.01270(9) 0.87392(9) 0.0804(8) Uani 1 1 d . . . C7 C 0.2422(2) -0.05009(10) 0.90707(11) 0.0992(10) Uani 1 1 d . . . H7 H 0.2403 -0.0850 0.8994 0.119 Uiso 1 1 calc R . . C8 C 0.24633(18) -0.03890(10) 0.94872(10) 0.0891(9) Uani 1 1 d . . . H8 H 0.2464 -0.0654 0.9687 0.107 Uiso 1 1 calc R . . C9 C 0.25046(14) 0.01325(9) 0.96146(7) 0.0667(6) Uani 1 1 d . . . C10 C 0.25438(16) 0.03063(11) 1.00345(8) 0.0801(8) Uani 1 1 d . . . H10 H 0.2538 0.0070 1.0257 0.096 Uiso 1 1 calc R . . C11 C 0.25909(16) 0.08236(12) 1.01118(7) 0.0819(8) Uani 1 1 d . . . H11 H 0.2622 0.0930 1.0393 0.098 Uiso 1 1 calc R . . C12 C 0.25957(14) 0.12144(10) 0.97941(7) 0.0670(7) Uani 1 1 d . . . C13 C 0.25398(12) 0.10507(8) 0.93756(6) 0.0507(6) Uani 1 1 d . . . C14 C 0.25174(12) 0.12969(7) 0.89506(6) 0.0494(5) Uani 1 1 d . . . C15 C 0.25244(14) 0.18152(8) 0.88062(8) 0.0615(6) Uani 1 1 d . . . C16 C 0.24991(13) 0.05095(8) 0.92945(6) 0.0528(5) Uani 1 1 d . . . C17 C 0.2387(2) 0.07087(12) 0.78340(7) 0.0946(9) Uani 1 1 d . . . H171 H 0.2396 0.0916 0.7581 0.114 Uiso 1 1 calc R . . H172 H 0.1802 0.0512 0.7844 0.114 Uiso 1 1 calc R . . H173 H 0.2924 0.0475 0.7833 0.114 Uiso 1 1 calc R . . C18 C 0.2321(3) -0.03349(12) 0.82920(12) 0.1520(18) Uani 1 1 d . . . H181 H 0.1771 -0.0183 0.8157 0.182 Uiso 1 1 calc R . . H182 H 0.2249 -0.0706 0.8300 0.182 Uiso 1 1 calc R . . H183 H 0.2888 -0.0248 0.8135 0.182 Uiso 1 1 calc R . . C19 C 0.2671(2) 0.17651(11) 0.99506(9) 0.1067(10) Uani 1 1 d . . . H191 H 0.3221 0.1929 0.9825 0.128 Uiso 1 1 calc R . . H192 H 0.2738 0.1765 1.0253 0.128 Uiso 1 1 calc R . . H193 H 0.2103 0.1953 0.9873 0.128 Uiso 1 1 calc R . . C20 C 0.25501(19) 0.22948(9) 0.90734(10) 0.0961(10) Uani 1 1 d . . . H201 H 0.2476 0.2595 0.8896 0.115 Uiso 1 1 calc R . . H202 H 0.3153 0.2314 0.9219 0.115 Uiso 1 1 calc R . . H203 H 0.2038 0.2283 0.9276 0.115 Uiso 1 1 calc R . . C21 C 0.2742(5) 0.1250 0.1250 0.081(3) Uani 1 2 d S . . C22 C 0.168(3) 0.127(2) 0.1387(12) 0.207(17) Uani 0.33 1 d P . . C23 C 0.170(3) 0.1031(14) 0.1287(12) 0.139(13) Uani 0.33 1 d P . . C24 C 0.2267(7) 0.1250 0.1250 0.077(4) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0690(13) 0.0693(13) 0.0879(15) 0.0309(12) -0.0038(10) -0.0010(9) N2 0.0680(13) 0.0866(15) 0.0677(13) 0.0274(12) 0.0030(10) 0.0004(10) C3 0.0523(12) 0.0800(16) 0.0505(13) 0.0107(11) 0.0026(9) 0.0019(10) C4 0.0456(11) 0.0526(11) 0.0494(11) 0.0036(9) 0.0002(8) 0.0006(8) C5 0.0578(12) 0.0467(11) 0.0554(13) 0.0017(9) -0.0058(9) -0.0003(9) C6 0.1090(19) 0.0530(14) 0.0791(16) -0.0066(12) -0.0142(14) -0.0001(12) C7 0.139(3) 0.0467(14) 0.112(2) 0.0095(14) -0.0156(19) -0.0033(14) C8 0.107(2) 0.0622(16) 0.098(2) 0.0297(15) -0.0065(15) 0.0019(14) C9 0.0648(14) 0.0702(15) 0.0651(15) 0.0195(11) -0.0050(10) 0.0022(11) C10 0.0786(17) 0.101(2) 0.0607(16) 0.0295(14) -0.0006(11) 0.0025(14) C11 0.0808(17) 0.116(2) 0.0489(14) 0.0033(14) -0.0021(11) 0.0021(14) C12 0.0616(13) 0.0847(16) 0.0548(13) -0.0092(12) -0.0004(10) -0.0020(11) C13 0.0452(11) 0.0581(12) 0.0488(12) -0.0014(9) -0.0008(8) 0.0003(8) C14 0.0429(10) 0.0495(11) 0.0557(12) 0.0043(9) -0.0008(8) -0.0002(8) C15 0.0541(12) 0.0507(12) 0.0796(16) 0.0104(11) -0.0050(10) -0.0005(9) C16 0.0512(11) 0.0535(12) 0.0536(11) 0.0100(10) -0.0032(9) 0.0000(8) C17 0.117(2) 0.116(2) 0.0509(14) -0.0022(14) 0.0075(14) 0.0066(16) C18 0.287(5) 0.068(2) 0.101(2) -0.0257(17) -0.030(3) -0.009(2) C19 0.148(3) 0.097(2) 0.0749(18) -0.0303(16) -0.0021(17) -0.0060(18) C20 0.112(2) 0.0498(14) 0.127(3) -0.0011(14) -0.0210(17) -0.0007(13) C21 0.099(6) 0.100(4) 0.045(2) -0.011(2) 0.000 0.000 C22 0.16(3) 0.26(4) 0.20(3) 0.11(3) -0.13(2) -0.12(2) C23 0.18(3) 0.148(18) 0.094(12) -0.040(17) -0.041(17) 0.07(2) C24 0.124(13) 0.062(4) 0.044(3) -0.013(3) 0.000 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C15 1.325(3) . ? N1 N2 1.329(3) . ? N2 C3 1.330(3) . ? C3 C4 1.410(3) . ? C3 C17 1.489(3) . ? C4 C14 1.411(3) . ? C4 C5 1.479(3) . ? C5 C6 1.385(3) . ? C5 C16 1.419(3) . ? C6 C7 1.422(4) . ? C6 C18 1.514(4) . ? C7 C8 1.347(4) . ? C7 H7 0.9300 . ? C8 C9 1.402(4) . ? C8 H8 0.9300 . ? C9 C10 1.400(4) . ? C9 C16 1.401(3) . ? C10 C11 1.355(4) . ? C10 H10 0.9300 . ? C11 C12 1.420(4) . ? C11 H11 0.9300 . ? C12 C13 1.389(3) . ? C12 C19 1.504(4) . ? C13 C16 1.417(3) . ? C13 C14 1.484(3) . ? C14 C15 1.409(3) . ? C15 C20 1.495(3) . ? C17 H171 0.9600 . ? C17 H172 0.9600 . ? C17 H173 0.9600 . ? C18 H181 0.9600 . ? C18 H182 0.9600 . ? C18 H183 0.9600 . ? C19 H191 0.9600 . ? C19 H192 0.9600 . ? C19 H193 0.9600 . ? C20 H201 0.9600 . ? C20 H202 0.9600 . ? C20 H203 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 N1 N2 121.79(19) . . ? N1 N2 C3 121.2(2) . . ? N2 C3 C4 120.8(2) . . ? N2 C3 C17 111.8(2) . . ? C4 C3 C17 127.4(2) . . ? C3 C4 C14 117.90(18) . . ? C3 C4 C5 133.27(18) . . ? C14 C4 C5 108.82(16) . . ? C6 C5 C16 117.9(2) . . ? C6 C5 C4 137.2(2) . . ? C16 C5 C4 104.87(16) . . ? C5 C6 C7 117.1(2) . . ? C5 C6 C18 126.3(3) . . ? C7 C6 C18 116.6(2) . . ? C8 C7 C6 125.1(3) . . ? C8 C7 H7 117.5 . . ? C6 C7 H7 117.5 . . ? C7 C8 C9 119.1(2) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C16 117.5(2) . . ? C10 C9 C8 125.4(2) . . ? C16 C9 C8 117.1(2) . . ? C11 C10 C9 119.1(2) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C10 C11 C12 124.7(2) . . ? C10 C11 H11 117.7 . . ? C12 C11 H11 117.7 . . ? C13 C12 C11 117.2(2) . . ? C13 C12 C19 127.0(2) . . ? C11 C12 C19 115.8(2) . . ? C12 C13 C16 118.2(2) . . ? C12 C13 C14 137.0(2) . . ? C16 C13 C14 104.79(16) . . ? C15 C14 C4 117.22(18) . . ? C15 C14 C13 134.12(19) . . ? C4 C14 C13 108.66(16) . . ? N1 C15 C14 121.1(2) . . ? N1 C15 C20 112.1(2) . . ? C14 C15 C20 126.8(2) . . ? C9 C16 C13 123.4(2) . . ? C9 C16 C5 123.8(2) . . ? C13 C16 C5 112.86(17) . . ? C3 C17 H171 109.5 . . ? C3 C17 H172 109.5 . . ? H171 C17 H172 109.5 . . ? C3 C17 H173 109.5 . . ? H171 C17 H173 109.5 . . ? H172 C17 H173 109.5 . . ? C6 C18 H181 109.5 . . ? C6 C18 H182 109.5 . . ? H181 C18 H182 109.5 . . ? C6 C18 H183 109.5 . . ? H181 C18 H183 109.5 . . ? H182 C18 H183 109.5 . . ? C12 C19 H191 109.5 . . ? C12 C19 H192 109.5 . . ? H191 C19 H192 109.5 . . ? C12 C19 H193 109.5 . . ? H191 C19 H193 109.5 . . ? H192 C19 H193 109.5 . . ? C15 C20 H201 109.5 . . ? C15 C20 H202 109.5 . . ? H201 C20 H202 109.5 . . ? C15 C20 H203 109.5 . . ? H201 C20 H203 109.5 . . ? H202 C20 H203 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N1 N2 C3 0.7(3) . . . . ? N1 N2 C3 C4 -1.1(3) . . . . ? N1 N2 C3 C17 178.6(2) . . . . ? N2 C3 C4 C14 0.2(3) . . . . ? C17 C3 C4 C14 -179.4(2) . . . . ? N2 C3 C4 C5 -179.57(19) . . . . ? C17 C3 C4 C5 0.9(4) . . . . ? C3 C4 C5 C6 -0.9(4) . . . . ? C14 C4 C5 C6 179.3(2) . . . . ? C3 C4 C5 C16 179.66(19) . . . . ? C14 C4 C5 C16 -0.1(2) . . . . ? C16 C5 C6 C7 -1.1(3) . . . . ? C4 C5 C6 C7 179.5(2) . . . . ? C16 C5 C6 C18 177.8(3) . . . . ? C4 C5 C6 C18 -1.6(5) . . . . ? C5 C6 C7 C8 1.3(4) . . . . ? C18 C6 C7 C8 -177.7(3) . . . . ? C6 C7 C8 C9 -0.7(4) . . . . ? C7 C8 C9 C10 179.6(3) . . . . ? C7 C8 C9 C16 0.1(3) . . . . ? C16 C9 C10 C11 -1.1(3) . . . . ? C8 C9 C10 C11 179.4(2) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C10 C11 C12 C13 0.6(3) . . . . ? C10 C11 C12 C19 -178.9(2) . . . . ? C11 C12 C13 C16 -1.1(3) . . . . ? C19 C12 C13 C16 178.3(2) . . . . ? C11 C12 C13 C14 179.7(2) . . . . ? C19 C12 C13 C14 -0.9(4) . . . . ? C3 C4 C14 C15 1.0(2) . . . . ? C5 C4 C14 C15 -179.19(16) . . . . ? C3 C4 C14 C13 -179.63(15) . . . . ? C5 C4 C14 C13 0.2(2) . . . . ? C12 C13 C14 C15 -1.7(4) . . . . ? C16 C13 C14 C15 179.03(19) . . . . ? C12 C13 C14 C4 179.1(2) . . . . ? C16 C13 C14 C4 -0.17(19) . . . . ? N2 N1 C15 C14 0.6(3) . . . . ? N2 N1 C15 C20 -179.36(19) . . . . ? C4 C14 C15 N1 -1.4(3) . . . . ? C13 C14 C15 N1 179.46(18) . . . . ? C4 C14 C15 C20 178.5(2) . . . . ? C13 C14 C15 C20 -0.6(4) . . . . ? C10 C9 C16 C13 0.6(3) . . . . ? C8 C9 C16 C13 -179.85(19) . . . . ? C10 C9 C16 C5 -179.58(19) . . . . ? C8 C9 C16 C5 0.0(3) . . . . ? C12 C13 C16 C9 0.5(3) . . . . ? C14 C13 C16 C9 179.97(17) . . . . ? C12 C13 C16 C5 -179.31(17) . . . . ? C14 C13 C16 C5 0.1(2) . . . . ? C6 C5 C16 C9 0.6(3) . . . . ? C4 C5 C16 C9 -179.88(17) . . . . ? C6 C5 C16 C13 -179.57(19) . . . . ? C4 C5 C16 C13 0.0(2) . . . . ? # End of CIF ============================================================ # End of CIF ============================================================ # Attachment '1,6-dimethyl-7,10-diphenyl-8,9-diazafluoranthene.cif' data_SG0714 _database_code_depnum_ccdc_archive 'CCDC 710122' _audit_creation_method SHELXL-97 _audit_creation_date 07-03-30 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C28 H20 N2' _chemical_formula_sum 'C28 H20 N2' _chemical_formula_weight 384.48 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 112 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 80 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 8 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.7712(6) _cell_length_b 9.9895(3) _cell_length_c 9.2316(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.6642(17) _cell_angle_gamma 90.00 _cell_volume 1942.32(10) _cell_formula_units_Z 4 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 2957 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.0769 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: ? Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.434(2) Frames collected: 433 Seconds exposure per frame: 129 Degrees rotation per frame: 1.8 Crystal-Detector distance (mm): 30.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 29059 _diffrn_reflns_av_R_equivalents 0.0890 _diffrn_reflns_av_sigmaI/netI 0.0544 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 30.01 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 2827 _reflns_number_gt 2042 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0895P)^2^+0.9433P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2827 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0882 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1688 _refine_ls_wR_factor_gt 0.1504 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.409 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.067 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.47151(6) 0.42404(13) 0.76415(16) 0.0285(3) Uani 1 1 d . . . C2 C 0.44335(7) 0.30904(14) 0.78610(16) 0.0189(3) Uani 1 1 d . . . C3 C 0.47233(6) 0.18485(13) 0.77729(14) 0.0150(3) Uani 1 1 d . . . C4 C 0.45663(6) 0.04482(14) 0.80530(14) 0.0143(3) Uani 1 1 d . . . C5 C 0.41479(6) -0.01963(15) 0.87409(14) 0.0157(3) Uani 1 1 d . . . C6 C 0.41562(7) -0.16212(15) 0.87414(16) 0.0193(3) Uani 1 1 d . . . H6 H 0.3867 -0.2074 0.9189 0.023 Uiso 1 1 calc R . . C7 C 0.45531(7) -0.23843(15) 0.81394(16) 0.0204(3) Uani 1 1 d . . . H7 H 0.4528 -0.3334 0.8152 0.024 Uiso 1 1 calc R . . C8 C 0.5000 -0.17401(19) 0.7500 0.0168(4) Uani 1 2 d S . . C9 C 0.5000 -0.03416(19) 0.7500 0.0145(4) Uani 1 2 d S . . C10 C 0.37896(7) 0.32912(14) 0.80976(17) 0.0205(3) Uani 1 1 d . . . C11 C 0.37001(9) 0.40894(17) 0.9269(2) 0.0321(4) Uani 1 1 d . . . H11 H 0.4053 0.4506 0.9934 0.039 Uiso 1 1 calc R . . C12 C 0.30942(10) 0.4273(2) 0.9460(2) 0.0417(5) Uani 1 1 d . . . H12 H 0.3036 0.4803 1.0268 0.050 Uiso 1 1 calc R . . C13 C 0.25748(9) 0.3692(2) 0.8487(2) 0.0393(5) Uani 1 1 d . . . H13 H 0.2162 0.3820 0.8630 0.047 Uiso 1 1 calc R . . C14 C 0.26565(8) 0.29234(19) 0.73036(19) 0.0325(4) Uani 1 1 d . . . H14 H 0.2300 0.2534 0.6622 0.039 Uiso 1 1 calc R . . C15 C 0.32646(7) 0.27234(17) 0.71172(17) 0.0243(4) Uani 1 1 d . . . H15 H 0.3321 0.2191 0.6308 0.029 Uiso 1 1 calc R . . C16 C 0.36996(7) 0.04629(15) 0.95210(16) 0.0203(3) Uani 1 1 d . . . H161 H 0.3878 0.1321 0.9942 0.030 Uiso 1 1 calc R . . H162 H 0.3639 -0.0119 1.0328 0.030 Uiso 1 1 calc R . . H163 H 0.3290 0.0616 0.8801 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0285(7) 0.0137(7) 0.0451(9) -0.0004(6) 0.0126(6) 0.0018(5) C2 0.0213(7) 0.0127(7) 0.0219(7) -0.0020(5) 0.0041(5) 0.0023(5) C3 0.0151(7) 0.0143(7) 0.0145(6) -0.0010(5) 0.0014(5) -0.0009(5) C4 0.0129(6) 0.0135(7) 0.0149(6) -0.0002(5) 0.0005(5) 0.0005(5) C5 0.0131(6) 0.0175(7) 0.0155(6) 0.0006(5) 0.0015(5) -0.0007(5) C6 0.0187(7) 0.0172(7) 0.0227(7) 0.0031(5) 0.0062(6) -0.0031(5) C7 0.0225(8) 0.0130(7) 0.0254(7) 0.0026(5) 0.0055(6) -0.0018(5) C8 0.0173(9) 0.0120(10) 0.0205(9) 0.000 0.0034(7) 0.000 C9 0.0148(9) 0.0126(9) 0.0149(8) 0.000 0.0017(7) 0.000 C10 0.0244(7) 0.0130(7) 0.0249(7) 0.0022(5) 0.0077(6) 0.0077(6) C11 0.0384(10) 0.0246(9) 0.0359(9) -0.0085(7) 0.0141(7) 0.0035(7) C12 0.0526(12) 0.0345(10) 0.0466(11) -0.0097(8) 0.0285(10) 0.0125(9) C13 0.0334(10) 0.0423(11) 0.0481(11) 0.0062(9) 0.0209(8) 0.0180(8) C14 0.0236(8) 0.0403(10) 0.0332(9) 0.0062(8) 0.0062(7) 0.0112(7) C15 0.0234(8) 0.0280(9) 0.0220(7) 0.0005(6) 0.0066(6) 0.0088(6) C16 0.0210(7) 0.0205(8) 0.0209(7) 0.0014(6) 0.0081(6) 0.0017(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N1 1.331(3) 2_656 ? N1 C2 1.341(2) . ? C2 C3 1.4035(19) . ? C2 C10 1.486(2) . ? C3 C3 1.419(3) 2_656 ? C3 C4 1.4781(19) . ? C4 C5 1.3930(18) . ? C4 C9 1.4208(17) . ? C5 C6 1.423(2) . ? C5 C16 1.5036(19) . ? C6 C7 1.371(2) . ? C6 H6 0.9500 . ? C7 C8 1.4142(16) . ? C7 H7 0.9500 . ? C8 C9 1.397(3) . ? C10 C15 1.387(2) . ? C10 C11 1.397(2) . ? C11 C12 1.386(3) . ? C11 H11 0.9500 . ? C12 C13 1.381(3) . ? C12 H12 0.9500 . ? C13 C14 1.383(3) . ? C13 H13 0.9500 . ? C14 C15 1.392(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H161 0.9800 . ? C16 H162 0.9800 . ? C16 H163 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 N1 C2 120.93(8) 2_656 . ? N1 C2 C3 121.25(13) . . ? N1 C2 C10 113.01(12) . . ? C3 C2 C10 125.63(13) . . ? C2 C3 C3 117.08(8) . 2_656 ? C2 C3 C4 134.35(13) . . ? C3 C3 C4 108.47(7) 2_656 . ? C5 C4 C9 118.54(13) . . ? C5 C4 C3 136.38(13) . . ? C9 C4 C3 104.99(12) . . ? C4 C5 C6 116.91(12) . . ? C4 C5 C16 126.48(13) . . ? C6 C5 C16 116.59(12) . . ? C7 C6 C5 124.41(13) . . ? C7 C6 H6 117.8 . . ? C5 C6 H6 117.8 . . ? C6 C7 C8 119.14(14) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C9 C8 C7 117.07(9) . . ? C7 C8 C7 125.86(19) 2_656 . ? C8 C9 C4 123.73(9) . . ? C4 C9 C4 112.53(17) 2_656 . ? C15 C10 C11 119.03(15) . . ? C15 C10 C2 120.08(13) . . ? C11 C10 C2 120.85(15) . . ? C12 C11 C10 119.83(17) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C13 C12 C11 120.71(16) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 119.93(16) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 119.60(17) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C10 C15 C14 120.88(15) . . ? C10 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C5 C16 H161 109.5 . . ? C5 C16 H162 109.5 . . ? H161 C16 H162 109.5 . . ? C5 C16 H163 109.5 . . ? H161 C16 H163 109.5 . . ? H162 C16 H163 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 N1 C2 C3 -1.2(3) 2_656 . . . ? N1 N1 C2 C10 -177.58(17) 2_656 . . . ? N1 C2 C3 C3 -9.1(2) . . . 2_656 ? C10 C2 C3 C3 166.79(15) . . . 2_656 ? N1 C2 C3 C4 174.87(14) . . . . ? C10 C2 C3 C4 -9.2(3) . . . . ? C2 C3 C4 C5 -13.6(3) . . . . ? C3 C3 C4 C5 170.14(15) 2_656 . . . ? C2 C3 C4 C9 170.05(14) . . . . ? C3 C3 C4 C9 -6.20(16) 2_656 . . . ? C9 C4 C5 C6 -4.42(17) . . . . ? C3 C4 C5 C6 179.61(14) . . . . ? C9 C4 C5 C16 173.81(11) . . . . ? C3 C4 C5 C16 -2.2(2) . . . . ? C4 C5 C6 C7 1.2(2) . . . . ? C16 C5 C6 C7 -177.18(13) . . . . ? C5 C6 C7 C8 1.6(2) . . . . ? C6 C7 C8 C9 -1.13(15) . . . . ? C6 C7 C8 C7 178.87(15) . . . 2_656 ? C7 C8 C9 C4 -2.26(9) 2_656 . . 2_656 ? C7 C8 C9 C4 177.74(9) . . . 2_656 ? C7 C8 C9 C4 -2.26(9) . . . . ? C5 C4 C9 C8 5.17(13) . . . . ? C3 C4 C9 C8 -177.71(6) . . . . ? C5 C4 C9 C4 -174.84(13) . . . 2_656 ? C3 C4 C9 C4 2.29(6) . . . 2_656 ? N1 C2 C10 C15 119.19(16) . . . . ? C3 C2 C10 C15 -57.0(2) . . . . ? N1 C2 C10 C11 -58.45(19) . . . . ? C3 C2 C10 C11 125.35(17) . . . . ? C15 C10 C11 C12 1.7(2) . . . . ? C2 C10 C11 C12 179.39(16) . . . . ? C10 C11 C12 C13 -1.1(3) . . . . ? C11 C12 C13 C14 -0.3(3) . . . . ? C12 C13 C14 C15 1.1(3) . . . . ? C11 C10 C15 C14 -1.0(2) . . . . ? C2 C10 C15 C14 -178.68(14) . . . . ? C13 C14 C15 C10 -0.4(3) . . . . ? # End of CIF ============================================================ # Attachment '2,5-di-tert-butyl-7,10-dicarboxamide-8,9-diazafluoran-thyne.cif' data_sg0718 _database_code_depnum_ccdc_archive 'CCDC 710123' _audit_creation_method SHELXL-97 _audit_creation_date 07-05-16 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C24 H26 N4 O2, 0.5(C H4 O)' _chemical_formula_sum 'C24.5 H28 N4 O2.5' _chemical_formula_weight 418.51 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 196 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 224 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 32 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 20 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 2/c 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 13 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 15.7180(7) _cell_length_b 13.3493(6) _cell_length_c 23.9219(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.478(2) _cell_angle_gamma 90.00 _cell_volume 5014.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 8679 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1784 _exptl_absorpt_coefficient_mu 0.0732 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: MeOH Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 1.421(1) Frames collected: 1115 Seconds exposure per frame: 175 Degrees rotation per frame: 0.5 Crystal-Detector distance (mm): 39.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 49418 _diffrn_reflns_av_R_equivalents 0.1150 _diffrn_reflns_av_sigmaI/netI 0.1166 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.03 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.988 _reflns_number_total 8767 _reflns_number_gt 5315 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1529P)^2^+2.6816P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8767 _refine_ls_number_parameters 553 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1478 _refine_ls_R_factor_gt 0.0933 _refine_ls_wR_factor_ref 0.2758 _refine_ls_wR_factor_gt 0.2436 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.444 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.102 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O17 O 0.38887(15) 0.37875(19) 0.25525(9) 0.0179(6) Uani 1 1 d . . . O27 O 0.02280(16) 0.4591(2) 0.07952(9) 0.0249(7) Uani 1 1 d . . . N1 N 0.1045(2) 0.4546(3) 0.21765(12) 0.0240(8) Uani 1 1 d . . . N2 N 0.17340(19) 0.4380(2) 0.25002(12) 0.0209(8) Uani 1 1 d . . . N18 N 0.2988(2) 0.4017(2) 0.32496(11) 0.0222(8) Uani 1 1 d . . . H181 H 0.3406 0.4047 0.3506 0.027 Uiso 1 1 calc R . . H182 H 0.2457 0.4079 0.3346 0.027 Uiso 1 1 calc R . . N28 N -0.04460(19) 0.4804(3) 0.15998(12) 0.0269(9) Uani 1 1 d . . . H281 H -0.0917 0.5008 0.1424 0.032 Uiso 1 1 calc R . . H282 H -0.0419 0.4765 0.1967 0.032 Uiso 1 1 calc R . . C3 C 0.2400(2) 0.3894(3) 0.23056(14) 0.0134(8) Uani 1 1 d . . . C4 C 0.2391(2) 0.3478(3) 0.17729(14) 0.0147(8) Uani 1 1 d . . . C5 C 0.2967(2) 0.2820(3) 0.14641(14) 0.0141(8) Uani 1 1 d . . . C6 C 0.3740(2) 0.2354(3) 0.15813(14) 0.0152(9) Uani 1 1 d . . . H6 H 0.4035 0.2462 0.1931 0.018 Uiso 1 1 calc R . . C7 C 0.4093(2) 0.1710(3) 0.11740(14) 0.0156(8) Uani 1 1 d . . . C8 C 0.3667(2) 0.1568(3) 0.06642(14) 0.0173(9) Uani 1 1 d . . . H8 H 0.3924 0.1171 0.0388 0.021 Uiso 1 1 calc R . . C9 C 0.2850(2) 0.2001(3) 0.05399(14) 0.0181(9) Uani 1 1 d . . . C10 C 0.2317(3) 0.1810(3) 0.00635(15) 0.0232(10) Uani 1 1 d . . . H10 H 0.2524 0.1411 -0.0230 0.028 Uiso 1 1 calc R . . C11 C 0.1494(3) 0.2192(3) 0.00132(15) 0.0223(9) Uani 1 1 d . . . C12 C 0.1203(3) 0.2844(3) 0.04375(14) 0.0201(9) Uani 1 1 d . . . H12 H 0.0649 0.3128 0.0402 0.024 Uiso 1 1 calc R . . C13 C 0.1732(2) 0.3064(3) 0.09034(13) 0.0134(8) Uani 1 1 d . . . C14 C 0.1641(2) 0.3636(3) 0.14289(14) 0.0141(8) Uani 1 1 d . . . C15 C 0.1003(2) 0.4219(3) 0.16459(14) 0.0177(9) Uani 1 1 d . . . C16 C 0.2532(2) 0.2618(3) 0.09484(14) 0.0135(8) Uani 1 1 d . . . C17 C 0.3159(2) 0.3880(3) 0.27182(14) 0.0128(8) Uani 1 1 d . . . C19 C 0.4907(2) 0.1122(3) 0.13384(15) 0.0184(9) Uani 1 1 d . . . C20 C 0.4657(3) 0.0333(3) 0.17680(15) 0.0256(10) Uani 1 1 d . . . H201 H 0.5161 -0.0057 0.1888 0.038 Uiso 1 1 calc R . . H202 H 0.4226 -0.0116 0.1598 0.038 Uiso 1 1 calc R . . H203 H 0.4425 0.0667 0.2093 0.038 Uiso 1 1 calc R . . C21 C 0.5598(2) 0.1822(3) 0.15964(18) 0.0300(10) Uani 1 1 d . . . H211 H 0.5762 0.2314 0.1316 0.045 Uiso 1 1 calc R . . H212 H 0.6097 0.1427 0.1718 0.045 Uiso 1 1 calc R . . H213 H 0.5374 0.2172 0.1919 0.045 Uiso 1 1 calc R . . C22 C 0.5272(3) 0.0574(3) 0.08354(16) 0.0318(11) Uani 1 1 d . . . H221 H 0.5342 0.1051 0.0529 0.048 Uiso 1 1 calc R . . H222 H 0.4879 0.0041 0.0710 0.048 Uiso 1 1 calc R . . H223 H 0.5825 0.0282 0.0946 0.048 Uiso 1 1 calc R . . C23 C 0.0876(3) 0.1907(3) -0.04653(16) 0.0299(11) Uani 1 1 d . . . C24 C 0.1260(4) 0.1175(4) -0.0871(2) 0.0698(19) Uani 1 1 d . . . H241 H 0.0858 0.1064 -0.1190 0.105 Uiso 1 1 calc R . . H242 H 0.1378 0.0537 -0.0680 0.105 Uiso 1 1 calc R . . H243 H 0.1792 0.1452 -0.1005 0.105 Uiso 1 1 calc R . . C25 C 0.0564(3) 0.2815(4) -0.07834(18) 0.0479(14) Uani 1 1 d . . . H251 H 0.0284 0.3273 -0.0529 0.072 Uiso 1 1 calc R . . H252 H 0.0158 0.2610 -0.1084 0.072 Uiso 1 1 calc R . . H253 H 0.1048 0.3156 -0.0945 0.072 Uiso 1 1 calc R . . C26 C 0.0093(4) 0.1405(4) -0.0216(2) 0.0639(17) Uani 1 1 d . . . H261 H -0.0195 0.1888 0.0019 0.096 Uiso 1 1 calc R . . H262 H 0.0278 0.0827 0.0011 0.096 Uiso 1 1 calc R . . H263 H -0.0300 0.1182 -0.0520 0.096 Uiso 1 1 calc R . . C27 C 0.0214(2) 0.4557(3) 0.13155(14) 0.0178(9) Uani 1 1 d . . . O47 O 0.56587(16) 0.4224(2) 0.09347(10) 0.0201(6) Uani 1 1 d . . . O57 O 0.20268(16) 0.4892(2) -0.09159(9) 0.0212(7) Uani 1 1 d . . . N31 N 0.28164(19) 0.4961(2) 0.04693(11) 0.0146(7) Uani 1 1 d . . . N32 N 0.34929(18) 0.4857(2) 0.08146(11) 0.0137(7) Uani 1 1 d . . . N48 N 0.4730(2) 0.4564(3) 0.15987(12) 0.0247(8) Uani 1 1 d . . . H481 H 0.5128 0.4547 0.1869 0.030 Uiso 1 1 calc R . . H482 H 0.4199 0.4688 0.1677 0.030 Uiso 1 1 calc R . . N58 N 0.13541(18) 0.5102(2) -0.01153(11) 0.0184(8) Uani 1 1 d . . . H581 H 0.0877 0.5276 -0.0296 0.022 Uiso 1 1 calc R . . H582 H 0.1380 0.5080 0.0253 0.022 Uiso 1 1 calc R . . C33 C 0.4205(2) 0.4417(3) 0.06428(13) 0.0123(8) Uani 1 1 d . . . C34 C 0.4252(2) 0.3981(3) 0.01076(13) 0.0106(8) Uani 1 1 d . . . C35 C 0.4886(2) 0.3389(3) -0.01786(13) 0.0128(8) Uani 1 1 d . . . C36 C 0.5704(2) 0.3044(3) -0.00564(14) 0.0148(8) Uani 1 1 d . . . H36 H 0.5977 0.3196 0.0295 0.018 Uiso 1 1 calc R . . C37 C 0.6135(2) 0.2464(3) -0.04520(14) 0.0161(9) Uani 1 1 d . . . C38 C 0.5729(2) 0.2248(3) -0.09647(14) 0.0186(9) Uani 1 1 d . . . H38 H 0.6020 0.1861 -0.1230 0.022 Uiso 1 1 calc R . . C39 C 0.4897(2) 0.2587(3) -0.11028(14) 0.0155(9) Uani 1 1 d . . . C40 C 0.4418(2) 0.2426(3) -0.16171(15) 0.0218(9) Uani 1 1 d . . . H40 H 0.4663 0.2043 -0.1904 0.026 Uiso 1 1 calc R . . C41 C 0.3618(2) 0.2807(3) -0.17067(14) 0.0184(9) Uani 1 1 d . . . C42 C 0.3244(2) 0.3391(3) -0.12857(14) 0.0182(9) Uani 1 1 d . . . H42 H 0.2692 0.3669 -0.1351 0.022 Uiso 1 1 calc R . . C43 C 0.3684(2) 0.3555(3) -0.07797(14) 0.0126(8) Uani 1 1 d . . . C44 C 0.3521(2) 0.4095(3) -0.02565(13) 0.0120(8) Uani 1 1 d . . . C45 C 0.2821(2) 0.4617(3) -0.00618(13) 0.0129(8) Uani 1 1 d . . . C46 C 0.4501(2) 0.3152(3) -0.07021(13) 0.0148(8) Uani 1 1 d . . . C47 C 0.4931(2) 0.4401(3) 0.10747(13) 0.0131(8) Uani 1 1 d . . . C49 C 0.7046(2) 0.2082(3) -0.03290(15) 0.0202(9) Uani 1 1 d . . . C50 C 0.7398(3) 0.2381(3) 0.02480(16) 0.0294(10) Uani 1 1 d . . . H501 H 0.7408 0.3113 0.0278 0.044 Uiso 1 1 calc R . . H502 H 0.7977 0.2118 0.0305 0.044 Uiso 1 1 calc R . . H503 H 0.7035 0.2103 0.0533 0.044 Uiso 1 1 calc R . . C51 C 0.7056(3) 0.0931(3) -0.03541(18) 0.0293(10) Uani 1 1 d . . . H511 H 0.6672 0.0661 -0.0079 0.044 Uiso 1 1 calc R . . H512 H 0.7636 0.0688 -0.0269 0.044 Uiso 1 1 calc R . . H513 H 0.6867 0.0710 -0.0730 0.044 Uiso 1 1 calc R . . C52 C 0.7640(2) 0.2488(3) -0.07683(16) 0.0270(10) Uani 1 1 d . . . H521 H 0.7459 0.2231 -0.1138 0.041 Uiso 1 1 calc R . . H522 H 0.8225 0.2271 -0.0676 0.041 Uiso 1 1 calc R . . H523 H 0.7616 0.3222 -0.0771 0.041 Uiso 1 1 calc R . . C53 C 0.3151(3) 0.2688(3) -0.22856(15) 0.0254(10) Uani 1 1 d . . . C54 C 0.3308(3) 0.1631(3) -0.25189(16) 0.0376(12) Uani 1 1 d . . . H541 H 0.3921 0.1528 -0.2555 0.056 Uiso 1 1 calc R . . H542 H 0.3016 0.1563 -0.2887 0.056 Uiso 1 1 calc R . . H543 H 0.3089 0.1129 -0.2263 0.056 Uiso 1 1 calc R . . C55 C 0.3533(3) 0.3451(3) -0.26806(17) 0.0447(13) Uani 1 1 d . . . H551 H 0.3478 0.4126 -0.2525 0.067 Uiso 1 1 calc R . . H552 H 0.3231 0.3418 -0.3047 0.067 Uiso 1 1 calc R . . H553 H 0.4137 0.3299 -0.2723 0.067 Uiso 1 1 calc R . . C56 C 0.2204(3) 0.2873(5) -0.22638(19) 0.0572(17) Uani 1 1 d . . . H561 H 0.1966 0.2439 -0.1979 0.086 Uiso 1 1 calc R . . H562 H 0.1929 0.2724 -0.2630 0.086 Uiso 1 1 calc R . . H563 H 0.2104 0.3575 -0.2168 0.086 Uiso 1 1 calc R . . C57 C 0.2030(2) 0.4873(3) -0.03960(14) 0.0133(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O17 0.0075(14) 0.0345(16) 0.0117(13) -0.0048(11) -0.0001(11) 0.0012(12) O27 0.0186(16) 0.0488(19) 0.0071(13) 0.0052(12) -0.0026(11) 0.0072(13) N1 0.0127(19) 0.045(2) 0.0137(17) 0.0019(15) -0.0010(14) 0.0033(16) N2 0.0120(18) 0.037(2) 0.0138(16) 0.0003(14) -0.0017(14) 0.0062(15) N18 0.0101(18) 0.050(2) 0.0062(15) -0.0015(14) -0.0019(13) 0.0046(15) N28 0.0120(19) 0.059(3) 0.0095(16) 0.0028(16) 0.0014(14) 0.0107(17) C3 0.010(2) 0.022(2) 0.0083(18) 0.0036(15) 0.0019(15) -0.0022(16) C4 0.014(2) 0.019(2) 0.0106(18) 0.0035(15) -0.0023(15) -0.0047(16) C5 0.012(2) 0.018(2) 0.0122(18) 0.0014(15) -0.0002(15) -0.0020(16) C6 0.013(2) 0.020(2) 0.0117(18) -0.0007(16) -0.0051(15) -0.0003(16) C7 0.017(2) 0.015(2) 0.0149(19) 0.0014(16) 0.0027(16) 0.0019(16) C8 0.021(2) 0.016(2) 0.0158(19) -0.0004(16) 0.0040(17) 0.0028(17) C9 0.026(2) 0.016(2) 0.0119(19) 0.0011(15) -0.0025(16) -0.0039(17) C10 0.029(3) 0.022(2) 0.018(2) -0.0042(17) -0.0062(18) -0.0027(19) C11 0.030(3) 0.021(2) 0.016(2) -0.0013(17) -0.0067(17) -0.0024(19) C12 0.022(2) 0.022(2) 0.016(2) 0.0039(16) -0.0028(17) -0.0035(17) C13 0.017(2) 0.016(2) 0.0071(17) 0.0018(15) -0.0039(15) -0.0076(16) C14 0.008(2) 0.025(2) 0.0093(18) 0.0037(15) -0.0007(15) -0.0021(16) C15 0.012(2) 0.031(2) 0.0094(18) 0.0054(16) -0.0006(16) 0.0002(17) C16 0.016(2) 0.0107(19) 0.0131(18) -0.0005(15) -0.0022(15) -0.0006(16) C17 0.011(2) 0.018(2) 0.0098(18) 0.0006(15) -0.0020(15) 0.0006(16) C19 0.013(2) 0.018(2) 0.023(2) -0.0007(16) -0.0035(16) 0.0002(16) C20 0.032(3) 0.023(2) 0.021(2) 0.0045(17) -0.0065(18) 0.0107(19) C21 0.012(2) 0.030(3) 0.047(3) -0.005(2) -0.0032(19) 0.0033(19) C22 0.032(3) 0.036(3) 0.028(2) 0.002(2) 0.007(2) 0.017(2) C23 0.039(3) 0.027(2) 0.021(2) -0.0033(18) -0.0216(19) -0.004(2) C24 0.086(5) 0.064(4) 0.054(3) -0.038(3) -0.049(3) 0.022(3) C25 0.061(4) 0.047(3) 0.033(3) 0.000(2) -0.032(2) -0.006(3) C26 0.067(4) 0.064(4) 0.057(3) 0.001(3) -0.033(3) -0.035(3) C27 0.008(2) 0.029(2) 0.017(2) 0.0046(17) 0.0021(16) 0.0042(17) O47 0.0099(15) 0.0368(17) 0.0132(13) -0.0056(11) -0.0028(11) -0.0006(12) O57 0.0172(15) 0.0391(17) 0.0073(13) 0.0021(11) 0.0025(11) 0.0063(12) N31 0.0129(17) 0.0207(18) 0.0101(15) 0.0012(13) -0.0002(13) 0.0010(13) N32 0.0112(17) 0.0177(17) 0.0120(15) -0.0042(13) -0.0025(13) -0.0016(13) N48 0.0177(19) 0.047(2) 0.0092(16) -0.0054(15) -0.0022(14) -0.0016(16) N58 0.0114(18) 0.037(2) 0.0063(15) 0.0032(14) -0.0009(13) 0.0065(15) C33 0.014(2) 0.016(2) 0.0065(17) 0.0018(15) -0.0011(15) -0.0004(16) C34 0.013(2) 0.0126(19) 0.0068(17) 0.0020(14) 0.0007(14) -0.0025(15) C35 0.011(2) 0.017(2) 0.0107(18) 0.0028(15) 0.0015(15) -0.0052(16) C36 0.015(2) 0.018(2) 0.0114(18) -0.0005(15) -0.0008(15) -0.0011(16) C37 0.015(2) 0.016(2) 0.0177(19) 0.0001(16) 0.0042(16) 0.0021(16) C38 0.019(2) 0.025(2) 0.0127(19) -0.0056(16) 0.0032(16) 0.0021(17) C39 0.017(2) 0.016(2) 0.0132(18) -0.0003(15) -0.0004(16) 0.0024(16) C40 0.023(2) 0.030(2) 0.0128(19) -0.0093(17) 0.0015(17) 0.0036(18) C41 0.019(2) 0.026(2) 0.0092(18) -0.0025(16) -0.0015(16) 0.0057(18) C42 0.018(2) 0.026(2) 0.0103(18) -0.0012(16) -0.0015(16) 0.0016(17) C43 0.012(2) 0.015(2) 0.0108(18) -0.0030(15) 0.0010(15) -0.0008(16) C44 0.010(2) 0.018(2) 0.0080(17) 0.0007(15) 0.0010(15) -0.0027(16) C45 0.014(2) 0.015(2) 0.0090(18) 0.0032(15) -0.0012(15) 0.0001(16) C46 0.016(2) 0.021(2) 0.0077(18) 0.0004(15) 0.0032(15) -0.0020(17) C47 0.014(2) 0.018(2) 0.0072(18) 0.0017(15) -0.0021(15) -0.0028(16) C49 0.014(2) 0.025(2) 0.021(2) -0.0059(17) 0.0006(17) 0.0074(17) C50 0.014(2) 0.043(3) 0.031(2) -0.008(2) -0.0044(18) 0.0086(19) C51 0.022(2) 0.027(3) 0.039(3) -0.001(2) -0.002(2) 0.0063(19) C52 0.013(2) 0.035(3) 0.033(2) -0.0021(19) 0.0017(18) 0.0019(18) C53 0.028(3) 0.034(3) 0.014(2) -0.0085(18) -0.0054(17) 0.0042(19) C54 0.055(3) 0.039(3) 0.017(2) -0.008(2) -0.016(2) -0.006(2) C55 0.077(4) 0.036(3) 0.020(2) -0.003(2) -0.014(2) 0.007(3) C56 0.031(3) 0.114(5) 0.025(3) -0.028(3) -0.015(2) 0.008(3) C57 0.008(2) 0.019(2) 0.0129(19) 0.0002(15) 0.0015(15) -0.0035(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O17 C17 1.235(4) . ? O27 C27 1.246(4) . ? N1 N2 1.322(4) . ? N1 C15 1.341(4) . ? N2 C3 1.332(4) . ? N18 C17 1.323(4) . ? N18 H181 0.8800 . ? N18 H182 0.8800 . ? N28 C27 1.307(4) . ? N28 H281 0.8800 . ? N28 H282 0.8800 . ? C3 C4 1.390(5) . ? C3 C17 1.516(5) . ? C4 C14 1.424(5) . ? C4 C5 1.482(5) . ? C5 C6 1.382(5) . ? C5 C16 1.410(5) . ? C6 C7 1.429(5) . ? C6 H6 0.9500 . ? C7 C8 1.379(5) . ? C7 C19 1.537(5) . ? C8 C9 1.427(5) . ? C8 H8 0.9500 . ? C9 C16 1.388(5) . ? C9 C10 1.408(5) . ? C10 C11 1.391(6) . ? C10 H10 0.9500 . ? C11 C12 1.427(5) . ? C11 C23 1.517(5) . ? C12 C13 1.393(5) . ? C12 H12 0.9500 . ? C13 C16 1.391(5) . ? C13 C14 1.484(5) . ? C14 C15 1.387(5) . ? C15 C27 1.510(5) . ? C19 C20 1.535(5) . ? C19 C22 1.540(5) . ? C19 C21 1.541(5) . ? C20 H201 0.9800 . ? C20 H202 0.9800 . ? C20 H203 0.9800 . ? C21 H211 0.9800 . ? C21 H212 0.9800 . ? C21 H213 0.9800 . ? C22 H221 0.9800 . ? C22 H222 0.9800 . ? C22 H223 0.9800 . ? C23 C25 1.503(6) . ? C23 C24 1.520(6) . ? C23 C26 1.543(6) . ? C24 H241 0.9800 . ? C24 H242 0.9800 . ? C24 H243 0.9800 . ? C25 H251 0.9800 . ? C25 H252 0.9800 . ? C25 H253 0.9800 . ? C26 H261 0.9800 . ? C26 H262 0.9800 . ? C26 H263 0.9800 . ? O47 C47 1.229(4) . ? O57 C57 1.244(4) . ? N31 N32 1.325(4) . ? N31 C45 1.351(4) . ? N32 C33 1.344(4) . ? N48 C47 1.324(4) . ? N48 H481 0.8800 . ? N48 H482 0.8800 . ? N58 C57 1.316(4) . ? N58 H581 0.8800 . ? N58 H582 0.8800 . ? C33 C34 1.412(5) . ? C33 C47 1.506(5) . ? C34 C44 1.419(5) . ? C34 C35 1.465(5) . ? C35 C36 1.384(5) . ? C35 C46 1.404(5) . ? C36 C37 1.418(5) . ? C36 H36 0.9500 . ? C37 C38 1.389(5) . ? C37 C49 1.535(5) . ? C38 C39 1.409(5) . ? C38 H38 0.9500 . ? C39 C46 1.388(5) . ? C39 C40 1.431(5) . ? C40 C41 1.365(5) . ? C40 H40 0.9500 . ? C41 C42 1.421(5) . ? C41 C53 1.548(5) . ? C42 C43 1.385(5) . ? C42 H42 0.9500 . ? C43 C46 1.397(5) . ? C43 C44 1.476(5) . ? C44 C45 1.399(5) . ? C45 C57 1.489(5) . ? C49 C50 1.518(5) . ? C49 C52 1.535(5) . ? C49 C51 1.538(6) . ? C50 H501 0.9800 . ? C50 H502 0.9800 . ? C50 H503 0.9800 . ? C51 H511 0.9800 . ? C51 H512 0.9800 . ? C51 H513 0.9800 . ? C52 H521 0.9800 . ? C52 H522 0.9800 . ? C52 H523 0.9800 . ? C53 C56 1.511(6) . ? C53 C55 1.530(6) . ? C53 C54 1.542(6) . ? C54 H541 0.9800 . ? C54 H542 0.9800 . ? C54 H543 0.9800 . ? C55 H551 0.9800 . ? C55 H552 0.9800 . ? C55 H553 0.9800 . ? C56 H561 0.9800 . ? C56 H562 0.9800 . ? C56 H563 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C15 120.4(3) . . ? N1 N2 C3 120.9(3) . . ? C17 N18 H181 120.0 . . ? C17 N18 H182 120.0 . . ? H181 N18 H182 120.0 . . ? C27 N28 H281 120.0 . . ? C27 N28 H282 120.0 . . ? H281 N28 H282 120.0 . . ? N2 C3 C4 122.5(3) . . ? N2 C3 C17 112.8(3) . . ? C4 C3 C17 124.7(3) . . ? C3 C4 C14 116.5(3) . . ? C3 C4 C5 135.4(3) . . ? C14 C4 C5 108.0(3) . . ? C6 C5 C16 118.7(3) . . ? C6 C5 C4 135.8(3) . . ? C16 C5 C4 105.4(3) . . ? C5 C6 C7 119.7(3) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 119.8(3) . . ? C8 C7 C19 121.6(3) . . ? C6 C7 C19 118.4(3) . . ? C7 C8 C9 121.8(3) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C16 C9 C10 117.2(4) . . ? C16 C9 C8 116.2(3) . . ? C10 C9 C8 126.4(3) . . ? C11 C10 C9 121.5(4) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 119.2(3) . . ? C10 C11 C23 122.4(3) . . ? C12 C11 C23 118.4(4) . . ? C13 C12 C11 119.9(4) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C16 C13 C12 118.6(3) . . ? C16 C13 C14 106.0(3) . . ? C12 C13 C14 135.3(3) . . ? C15 C14 C4 117.4(3) . . ? C15 C14 C13 134.7(3) . . ? C4 C14 C13 107.8(3) . . ? N1 C15 C14 122.0(3) . . ? N1 C15 C27 113.8(3) . . ? C14 C15 C27 124.2(3) . . ? C9 C16 C13 123.4(3) . . ? C9 C16 C5 123.6(3) . . ? C13 C16 C5 112.9(3) . . ? O17 C17 N18 123.5(3) . . ? O17 C17 C3 120.5(3) . . ? N18 C17 C3 115.9(3) . . ? C20 C19 C7 106.7(3) . . ? C20 C19 C22 108.2(3) . . ? C7 C19 C22 112.1(3) . . ? C20 C19 C21 110.2(3) . . ? C7 C19 C21 110.9(3) . . ? C22 C19 C21 108.8(3) . . ? C19 C20 H201 109.5 . . ? C19 C20 H202 109.5 . . ? H201 C20 H202 109.5 . . ? C19 C20 H203 109.5 . . ? H201 C20 H203 109.5 . . ? H202 C20 H203 109.5 . . ? C19 C21 H211 109.5 . . ? C19 C21 H212 109.5 . . ? H211 C21 H212 109.5 . . ? C19 C21 H213 109.5 . . ? H211 C21 H213 109.5 . . ? H212 C21 H213 109.5 . . ? C19 C22 H221 109.5 . . ? C19 C22 H222 109.5 . . ? H221 C22 H222 109.5 . . ? C19 C22 H223 109.5 . . ? H221 C22 H223 109.5 . . ? H222 C22 H223 109.5 . . ? C25 C23 C11 111.3(3) . . ? C25 C23 C24 109.0(4) . . ? C11 C23 C24 112.6(4) . . ? C25 C23 C26 107.3(4) . . ? C11 C23 C26 108.2(3) . . ? C24 C23 C26 108.3(4) . . ? C23 C24 H241 109.5 . . ? C23 C24 H242 109.5 . . ? H241 C24 H242 109.5 . . ? C23 C24 H243 109.5 . . ? H241 C24 H243 109.5 . . ? H242 C24 H243 109.5 . . ? C23 C25 H251 109.5 . . ? C23 C25 H252 109.5 . . ? H251 C25 H252 109.5 . . ? C23 C25 H253 109.5 . . ? H251 C25 H253 109.5 . . ? H252 C25 H253 109.5 . . ? C23 C26 H261 109.5 . . ? C23 C26 H262 109.5 . . ? H261 C26 H262 109.5 . . ? C23 C26 H263 109.5 . . ? H261 C26 H263 109.5 . . ? H262 C26 H263 109.5 . . ? O27 C27 N28 124.0(3) . . ? O27 C27 C15 119.0(3) . . ? N28 C27 C15 117.1(3) . . ? N32 N31 C45 120.9(3) . . ? N31 N32 C33 120.8(3) . . ? C47 N48 H481 120.0 . . ? C47 N48 H482 120.0 . . ? H481 N48 H482 120.0 . . ? C57 N58 H581 120.0 . . ? C57 N58 H582 120.0 . . ? H581 N58 H582 120.0 . . ? N32 C33 C34 122.3(3) . . ? N32 C33 C47 114.4(3) . . ? C34 C33 C47 123.3(3) . . ? C33 C34 C44 116.1(3) . . ? C33 C34 C35 135.2(3) . . ? C44 C34 C35 108.7(3) . . ? C36 C35 C46 118.3(3) . . ? C36 C35 C34 136.5(3) . . ? C46 C35 C34 105.2(3) . . ? C35 C36 C37 120.5(3) . . ? C35 C36 H36 119.8 . . ? C37 C36 H36 119.8 . . ? C38 C37 C36 119.2(3) . . ? C38 C37 C49 119.3(3) . . ? C36 C37 C49 121.5(3) . . ? C37 C38 C39 121.8(3) . . ? C37 C38 H38 119.1 . . ? C39 C38 H38 119.1 . . ? C46 C39 C38 116.9(3) . . ? C46 C39 C40 116.1(3) . . ? C38 C39 C40 127.0(3) . . ? C41 C40 C39 121.7(3) . . ? C41 C40 H40 119.1 . . ? C39 C40 H40 119.1 . . ? C40 C41 C42 120.0(3) . . ? C40 C41 C53 120.0(3) . . ? C42 C41 C53 119.7(3) . . ? C43 C42 C41 120.0(3) . . ? C43 C42 H42 120.0 . . ? C41 C42 H42 120.0 . . ? C42 C43 C46 118.5(3) . . ? C42 C43 C44 136.0(3) . . ? C46 C43 C44 105.5(3) . . ? C45 C44 C34 118.5(3) . . ? C45 C44 C43 133.9(3) . . ? C34 C44 C43 107.6(3) . . ? N31 C45 C44 121.2(3) . . ? N31 C45 C57 112.9(3) . . ? C44 C45 C57 125.9(3) . . ? C39 C46 C43 123.7(3) . . ? C39 C46 C35 123.3(3) . . ? C43 C46 C35 113.0(3) . . ? O47 C47 N48 123.5(3) . . ? O47 C47 C33 120.2(3) . . ? N48 C47 C33 116.3(3) . . ? C50 C49 C52 108.8(3) . . ? C50 C49 C37 112.8(3) . . ? C52 C49 C37 110.0(3) . . ? C50 C49 C51 107.1(3) . . ? C52 C49 C51 108.6(3) . . ? C37 C49 C51 109.6(3) . . ? C49 C50 H501 109.5 . . ? C49 C50 H502 109.5 . . ? H501 C50 H502 109.5 . . ? C49 C50 H503 109.5 . . ? H501 C50 H503 109.5 . . ? H502 C50 H503 109.5 . . ? C49 C51 H511 109.5 . . ? C49 C51 H512 109.5 . . ? H511 C51 H512 109.5 . . ? C49 C51 H513 109.5 . . ? H511 C51 H513 109.5 . . ? H512 C51 H513 109.5 . . ? C49 C52 H521 109.5 . . ? C49 C52 H522 109.5 . . ? H521 C52 H522 109.5 . . ? C49 C52 H523 109.5 . . ? H521 C52 H523 109.5 . . ? H522 C52 H523 109.5 . . ? C56 C53 C55 109.1(4) . . ? C56 C53 C54 109.6(4) . . ? C55 C53 C54 108.2(3) . . ? C56 C53 C41 112.5(3) . . ? C55 C53 C41 107.4(3) . . ? C54 C53 C41 109.9(3) . . ? C53 C54 H541 109.5 . . ? C53 C54 H542 109.5 . . ? H541 C54 H542 109.5 . . ? C53 C54 H543 109.5 . . ? H541 C54 H543 109.5 . . ? H542 C54 H543 109.5 . . ? C53 C55 H551 109.5 . . ? C53 C55 H552 109.5 . . ? H551 C55 H552 109.5 . . ? C53 C55 H553 109.5 . . ? H551 C55 H553 109.5 . . ? H552 C55 H553 109.5 . . ? C53 C56 H561 109.5 . . ? C53 C56 H562 109.5 . . ? H561 C56 H562 109.5 . . ? C53 C56 H563 109.5 . . ? H561 C56 H563 109.5 . . ? H562 C56 H563 109.5 . . ? O57 C57 N58 122.5(3) . . ? O57 C57 C45 120.6(3) . . ? N58 C57 C45 116.9(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N1 N2 C3 0.6(5) . . . . ? N1 N2 C3 C4 -4.6(5) . . . . ? N1 N2 C3 C17 173.6(3) . . . . ? N2 C3 C4 C14 2.9(5) . . . . ? C17 C3 C4 C14 -175.1(3) . . . . ? N2 C3 C4 C5 -172.0(4) . . . . ? C17 C3 C4 C5 10.1(6) . . . . ? C3 C4 C5 C6 0.3(7) . . . . ? C14 C4 C5 C6 -174.9(4) . . . . ? C3 C4 C5 C16 175.3(4) . . . . ? C14 C4 C5 C16 0.1(4) . . . . ? C16 C5 C6 C7 2.1(5) . . . . ? C4 C5 C6 C7 176.6(4) . . . . ? C5 C6 C7 C8 0.8(5) . . . . ? C5 C6 C7 C19 -174.0(3) . . . . ? C6 C7 C8 C9 -3.8(5) . . . . ? C19 C7 C8 C9 170.9(3) . . . . ? C7 C8 C9 C16 3.6(5) . . . . ? C7 C8 C9 C10 -171.9(4) . . . . ? C16 C9 C10 C11 -2.5(5) . . . . ? C8 C9 C10 C11 173.0(4) . . . . ? C9 C10 C11 C12 4.1(6) . . . . ? C9 C10 C11 C23 -173.3(4) . . . . ? C10 C11 C12 C13 -2.1(5) . . . . ? C23 C11 C12 C13 175.4(3) . . . . ? C11 C12 C13 C16 -1.4(5) . . . . ? C11 C12 C13 C14 -175.5(4) . . . . ? C3 C4 C14 C15 2.3(5) . . . . ? C5 C4 C14 C15 178.6(3) . . . . ? C3 C4 C14 C13 -175.2(3) . . . . ? C5 C4 C14 C13 1.0(4) . . . . ? C16 C13 C14 C15 -178.7(4) . . . . ? C12 C13 C14 C15 -4.0(7) . . . . ? C16 C13 C14 C4 -1.7(4) . . . . ? C12 C13 C14 C4 172.9(4) . . . . ? N2 N1 C15 C14 4.9(6) . . . . ? N2 N1 C15 C27 -174.2(3) . . . . ? C4 C14 C15 N1 -6.2(5) . . . . ? C13 C14 C15 N1 170.5(4) . . . . ? C4 C14 C15 C27 172.8(3) . . . . ? C13 C14 C15 C27 -10.5(7) . . . . ? C10 C9 C16 C13 -1.2(5) . . . . ? C8 C9 C16 C13 -177.2(3) . . . . ? C10 C9 C16 C5 175.4(3) . . . . ? C8 C9 C16 C5 -0.6(5) . . . . ? C12 C13 C16 C9 3.1(5) . . . . ? C14 C13 C16 C9 178.8(3) . . . . ? C12 C13 C16 C5 -173.8(3) . . . . ? C14 C13 C16 C5 1.9(4) . . . . ? C6 C5 C16 C9 -2.2(5) . . . . ? C4 C5 C16 C9 -178.2(3) . . . . ? C6 C5 C16 C13 174.7(3) . . . . ? C4 C5 C16 C13 -1.3(4) . . . . ? N2 C3 C17 O17 -154.7(3) . . . . ? C4 C3 C17 O17 23.4(5) . . . . ? N2 C3 C17 N18 22.3(4) . . . . ? C4 C3 C17 N18 -159.5(3) . . . . ? C8 C7 C19 C20 -105.5(4) . . . . ? C6 C7 C19 C20 69.2(4) . . . . ? C8 C7 C19 C22 12.7(5) . . . . ? C6 C7 C19 C22 -172.5(3) . . . . ? C8 C7 C19 C21 134.5(4) . . . . ? C6 C7 C19 C21 -50.8(4) . . . . ? C10 C11 C23 C25 -122.8(4) . . . . ? C12 C11 C23 C25 59.8(5) . . . . ? C10 C11 C23 C24 -0.1(6) . . . . ? C12 C11 C23 C24 -177.5(4) . . . . ? C10 C11 C23 C26 119.5(5) . . . . ? C12 C11 C23 C26 -57.9(5) . . . . ? N1 C15 C27 O27 156.7(4) . . . . ? C14 C15 C27 O27 -22.4(6) . . . . ? N1 C15 C27 N28 -22.9(5) . . . . ? C14 C15 C27 N28 158.0(4) . . . . ? C45 N31 N32 C33 0.9(5) . . . . ? N31 N32 C33 C34 -4.8(5) . . . . ? N31 N32 C33 C47 177.1(3) . . . . ? N32 C33 C34 C44 4.4(5) . . . . ? C47 C33 C34 C44 -177.8(3) . . . . ? N32 C33 C34 C35 -173.7(3) . . . . ? C47 C33 C34 C35 4.2(6) . . . . ? C33 C34 C35 C36 -2.9(7) . . . . ? C44 C34 C35 C36 179.0(4) . . . . ? C33 C34 C35 C46 176.9(4) . . . . ? C44 C34 C35 C46 -1.2(4) . . . . ? C46 C35 C36 C37 -0.1(5) . . . . ? C34 C35 C36 C37 179.7(4) . . . . ? C35 C36 C37 C38 0.1(5) . . . . ? C35 C36 C37 C49 179.3(3) . . . . ? C36 C37 C38 C39 -0.1(5) . . . . ? C49 C37 C38 C39 -179.4(3) . . . . ? C37 C38 C39 C46 0.2(5) . . . . ? C37 C38 C39 C40 179.1(4) . . . . ? C46 C39 C40 C41 0.1(6) . . . . ? C38 C39 C40 C41 -178.9(4) . . . . ? C39 C40 C41 C42 0.6(6) . . . . ? C39 C40 C41 C53 175.1(3) . . . . ? C40 C41 C42 C43 -1.4(6) . . . . ? C53 C41 C42 C43 -175.8(3) . . . . ? C41 C42 C43 C46 1.3(5) . . . . ? C41 C42 C43 C44 -179.9(4) . . . . ? C33 C34 C44 C45 -0.2(5) . . . . ? C35 C34 C44 C45 178.3(3) . . . . ? C33 C34 C44 C43 -177.6(3) . . . . ? C35 C34 C44 C43 0.9(4) . . . . ? C42 C43 C44 C45 4.0(7) . . . . ? C46 C43 C44 C45 -177.1(4) . . . . ? C42 C43 C44 C34 -179.2(4) . . . . ? C46 C43 C44 C34 -0.2(4) . . . . ? N32 N31 C45 C44 3.3(5) . . . . ? N32 N31 C45 C57 -175.6(3) . . . . ? C34 C44 C45 N31 -3.5(5) . . . . ? C43 C44 C45 N31 173.1(4) . . . . ? C34 C44 C45 C57 175.2(3) . . . . ? C43 C44 C45 C57 -8.2(6) . . . . ? C38 C39 C46 C43 178.9(3) . . . . ? C40 C39 C46 C43 -0.2(5) . . . . ? C38 C39 C46 C35 -0.1(5) . . . . ? C40 C39 C46 C35 -179.2(3) . . . . ? C42 C43 C46 C39 -0.5(5) . . . . ? C44 C43 C46 C39 -179.7(3) . . . . ? C42 C43 C46 C35 178.6(3) . . . . ? C44 C43 C46 C35 -0.6(4) . . . . ? C36 C35 C46 C39 0.1(5) . . . . ? C34 C35 C46 C39 -179.7(3) . . . . ? C36 C35 C46 C43 -179.0(3) . . . . ? C34 C35 C46 C43 1.1(4) . . . . ? N32 C33 C47 O47 -164.2(3) . . . . ? C34 C33 C47 O47 17.8(5) . . . . ? N32 C33 C47 N48 17.3(5) . . . . ? C34 C33 C47 N48 -160.7(3) . . . . ? C38 C37 C49 C50 -179.9(3) . . . . ? C36 C37 C49 C50 0.9(5) . . . . ? C38 C37 C49 C52 58.5(4) . . . . ? C36 C37 C49 C52 -120.7(4) . . . . ? C38 C37 C49 C51 -60.8(4) . . . . ? C36 C37 C49 C51 120.0(4) . . . . ? C40 C41 C53 C56 163.2(4) . . . . ? C42 C41 C53 C56 -22.4(6) . . . . ? C40 C41 C53 C55 -76.8(5) . . . . ? C42 C41 C53 C55 97.6(4) . . . . ? C40 C41 C53 C54 40.7(5) . . . . ? C42 C41 C53 C54 -144.9(4) . . . . ? N31 C45 C57 O57 158.0(3) . . . . ? C44 C45 C57 O57 -20.8(5) . . . . ? N31 C45 C57 N58 -20.1(4) . . . . ? C44 C45 C57 N58 161.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N18 H181 O47 0.88 1.96 2.837(4) 176 2_655 yes N18 H182 O57 0.88 2.36 2.941(4) 124 4_566 yes N28 H281 O57 0.88 2.09 2.943(4) 165 3_565 yes N28 H282 N1 0.88 2.33 3.133(4) 152 2 yes N48 H481 O17 0.88 2.27 3.087(4) 155 2_655 yes N48 H482 O17 0.88 2.48 2.879(4) 108 . yes N58 H582 O27 0.88 2.36 2.945(4) 124 . yes N58 H581 O27 0.88 2.07 2.941(4) 169 3_565 yes # End of CIF ============================================================ # Attachment '7,10-bis(2-hydroxyphenyl)-1,6-dimethyl-8,9-diazafluo-ranthene.cif' data_SG0727 _database_code_depnum_ccdc_archive 'CCDC 710124' _audit_creation_method SHELXL-97 _audit_creation_date 07-06-19 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C28 H20 N2 O2, 2(C H Cl3)' _chemical_formula_sum 'C30 H22 Cl6 N2 O2' _chemical_formula_weight 655.23 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 120 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 88 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; Cl Cl 24 0.1484 0.1585 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 8 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 8 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.6105(4) _cell_length_b 18.4987(4) _cell_length_c 11.5185(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.0695(14) _cell_angle_gamma 90.00 _cell_volume 2924.12(13) _cell_formula_units_Z 4 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 22530 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description tablet _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.619 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_absorpt_correction_T_min 0.898 _exptl_absorpt_correction_T_max 0.975 _exptl_special_details ; Solvent used: dichloromethane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.540(2) Frames collected: 341 Seconds exposure per frame: 70 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 38403 _diffrn_reflns_av_R_equivalents 0.0894 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 30.04 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.04 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 4282 _reflns_number_gt 2786 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0746P)^2^+3.6131P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom & difmap' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0055(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4282 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1010 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1608 _refine_ls_wR_factor_gt 0.1391 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.511 _refine_diff_density_min -0.598 _refine_diff_density_rms 0.082 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.52502(10) 0.43979(8) -0.05704(13) 0.0236(3) Uani 1 1 d . . . H1 H 0.526(2) 0.4780(16) -0.101(3) 0.042(8) Uiso 1 1 d . . . N1 N 0.47906(12) 0.42974(9) 0.18812(15) 0.0208(4) Uani 1 1 d . . . C2 C 0.46398(14) 0.36722(10) 0.12436(18) 0.0199(4) Uani 1 1 d . . . C3 C 0.48879(14) 0.30091(10) 0.18543(18) 0.0203(4) Uani 1 1 d . . . C4 C 0.48992(14) 0.22533(11) 0.1438(2) 0.0249(4) Uani 1 1 d . . . C5 C 0.49092(16) 0.19197(13) 0.0364(2) 0.0332(5) Uani 1 1 d . . . C6 C 0.49592(19) 0.11463(14) 0.0393(3) 0.0451(7) Uani 1 1 d . . . H6 H 0.4975 0.0902 -0.0325 0.054 Uiso 1 1 calc R . . C7 C 0.4985(2) 0.07402(13) 0.1395(3) 0.0494(7) Uani 1 1 d . . . H7 H 0.4993 0.0228 0.1344 0.059 Uiso 1 1 calc R . . C8 C 0.5000 0.10719(16) 0.2500 0.0377(8) Uani 1 2 d S . . C9 C 0.5000 0.18337(16) 0.2500 0.0275(6) Uani 1 2 d S . . C10 C 0.40456(14) 0.37217(11) -0.00946(18) 0.0218(4) Uani 1 1 d . . . C11 C 0.43340(14) 0.41079(11) -0.09530(18) 0.0221(4) Uani 1 1 d . . . C12 C 0.37105(16) 0.41500(13) -0.2178(2) 0.0310(5) Uani 1 1 d . . . H12 H 0.3896 0.4423 -0.2759 0.037 Uiso 1 1 calc R . . C13 C 0.28219(17) 0.37953(14) -0.2551(2) 0.0366(5) Uani 1 1 d . . . H13 H 0.2402 0.3826 -0.3387 0.044 Uiso 1 1 calc R . . C14 C 0.25422(17) 0.33958(14) -0.1713(2) 0.0337(5) Uani 1 1 d . . . H14 H 0.1939 0.3144 -0.1974 0.040 Uiso 1 1 calc R . . C15 C 0.31498(15) 0.33662(12) -0.0493(2) 0.0267(4) Uani 1 1 d . . . H15 H 0.2953 0.3099 0.0086 0.032 Uiso 1 1 calc R . . C16 C 0.4914(2) 0.22936(15) -0.0790(2) 0.0409(6) Uani 1 1 d . . . H161 H 0.4242 0.2386 -0.1329 0.061 Uiso 1 1 calc R . . H162 H 0.5238 0.1985 -0.1224 0.061 Uiso 1 1 calc R . . H163 H 0.5265 0.2753 -0.0572 0.061 Uiso 1 1 calc R . . Cl1 Cl 0.79377(7) 0.46471(5) 0.08990(9) 0.0690(3) Uani 1 1 d . . . Cl2 Cl 0.76344(7) 0.41182(6) 0.30921(7) 0.0723(3) Uani 1 1 d . . . Cl3 Cl 0.73856(8) 0.31650(5) 0.10389(9) 0.0735(3) Uani 1 1 d . . . C17 C 0.72743(18) 0.40586(15) 0.1486(2) 0.0400(6) Uani 1 1 d . . . H17 H 0.6572 0.4199 0.1132 0.048 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0242(7) 0.0248(7) 0.0218(7) 0.0011(6) 0.0078(6) -0.0043(6) N1 0.0257(8) 0.0180(8) 0.0183(8) -0.0002(6) 0.0070(6) -0.0003(6) C2 0.0219(9) 0.0194(9) 0.0202(9) 0.0000(7) 0.0096(7) -0.0019(7) C3 0.0197(9) 0.0181(9) 0.0242(10) -0.0020(7) 0.0089(7) -0.0025(7) C4 0.0217(9) 0.0175(9) 0.0356(11) -0.0063(8) 0.0098(8) -0.0016(7) C5 0.0259(11) 0.0297(11) 0.0424(13) -0.0143(10) 0.0096(10) -0.0014(9) C6 0.0409(14) 0.0310(13) 0.0599(17) -0.0241(12) 0.0125(12) 0.0003(11) C7 0.0465(15) 0.0185(11) 0.080(2) -0.0124(13) 0.0170(14) 0.0007(10) C8 0.0300(16) 0.0149(14) 0.065(2) 0.000 0.0119(16) 0.000 C9 0.0232(14) 0.0176(13) 0.0405(17) 0.000 0.0092(12) 0.000 C10 0.0256(10) 0.0200(9) 0.0200(9) -0.0026(8) 0.0080(7) -0.0023(8) C11 0.0243(10) 0.0226(9) 0.0201(9) -0.0018(7) 0.0083(7) -0.0015(8) C12 0.0326(11) 0.0396(12) 0.0205(10) 0.0006(9) 0.0087(8) -0.0039(9) C13 0.0333(12) 0.0494(14) 0.0212(10) -0.0036(10) 0.0018(9) -0.0050(11) C14 0.0271(11) 0.0402(13) 0.0305(12) -0.0069(10) 0.0056(9) -0.0088(9) C15 0.0277(10) 0.0280(10) 0.0253(10) -0.0017(8) 0.0105(8) -0.0065(8) C16 0.0451(14) 0.0457(14) 0.0360(13) -0.0175(11) 0.0192(11) 0.0007(11) Cl1 0.0923(7) 0.0584(5) 0.0779(6) -0.0094(4) 0.0572(5) -0.0265(4) Cl2 0.0846(6) 0.0965(7) 0.0370(4) 0.0136(4) 0.0223(4) 0.0295(5) Cl3 0.0912(7) 0.0433(4) 0.0706(6) -0.0015(4) 0.0081(5) -0.0086(4) C17 0.0333(12) 0.0469(14) 0.0361(13) 0.0081(11) 0.0071(10) -0.0038(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.367(2) . ? O1 H1 0.87(3) . ? N1 N1 1.345(3) 2_655 ? N1 C2 1.347(3) . ? C2 C3 1.399(3) . ? C2 C10 1.490(3) . ? C3 C3 1.409(4) 2_655 ? C3 C4 1.480(3) . ? C4 C5 1.386(3) . ? C4 C9 1.413(3) . ? C5 C6 1.432(3) . ? C5 C16 1.501(4) . ? C6 C7 1.366(5) . ? C6 H6 0.9500 . ? C7 C8 1.407(3) . ? C7 H7 0.9500 . ? C8 C9 1.409(4) . ? C10 C15 1.394(3) . ? C10 C11 1.397(3) . ? C11 C12 1.394(3) . ? C12 C13 1.385(3) . ? C12 H12 0.9500 . ? C13 C14 1.384(4) . ? C13 H13 0.9500 . ? C14 C15 1.382(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H161 0.9800 . ? C16 H162 0.9800 . ? C16 H163 0.9800 . ? Cl1 C17 1.741(3) . ? Cl2 C17 1.744(3) . ? Cl3 C17 1.756(3) . ? C17 H17 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O1 H1 109.5(19) . . ? N1 N1 C2 120.52(11) 2_655 . ? N1 C2 C3 120.87(17) . . ? N1 C2 C10 116.07(17) . . ? C3 C2 C10 122.20(17) . . ? C2 C3 C3 117.21(12) . 2_655 ? C2 C3 C4 134.05(18) . . ? C3 C3 C4 108.52(12) 2_655 . ? C5 C4 C9 119.9(2) . . ? C5 C4 C3 135.6(2) . . ? C9 C4 C3 104.34(18) . . ? C4 C5 C6 116.1(2) . . ? C4 C5 C16 126.1(2) . . ? C6 C5 C16 117.7(2) . . ? C7 C6 C5 123.7(2) . . ? C7 C6 H6 118.1 . . ? C5 C6 H6 118.1 . . ? C6 C7 C8 120.8(2) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C7 C8 C7 128.3(3) . 2_655 ? C7 C8 C9 115.86(16) . . ? C8 C9 C4 123.31(13) . . ? C4 C9 C4 113.4(3) . 2_655 ? C15 C10 C11 119.05(18) . . ? C15 C10 C2 117.33(18) . . ? C11 C10 C2 123.61(17) . . ? O1 C11 C12 122.12(18) . . ? O1 C11 C10 118.18(17) . . ? C12 C11 C10 119.59(19) . . ? C13 C12 C11 120.3(2) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 120.5(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 119.3(2) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C10 121.2(2) . . ? C14 C15 H15 119.4 . . ? C10 C15 H15 119.4 . . ? C5 C16 H161 109.5 . . ? C5 C16 H162 109.5 . . ? H161 C16 H162 109.5 . . ? C5 C16 H163 109.5 . . ? H161 C16 H163 109.5 . . ? H162 C16 H163 109.5 . . ? Cl1 C17 Cl2 111.52(15) . . ? Cl1 C17 Cl3 110.77(16) . . ? Cl2 C17 Cl3 110.26(15) . . ? Cl1 C17 H17 108.1 . . ? Cl2 C17 H17 108.1 . . ? Cl3 C17 H17 108.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 N1 C2 C3 1.9(3) 2_655 . . . ? N1 N1 C2 C10 171.5(2) 2_655 . . . ? N1 C2 C3 C3 12.4(3) . . . 2_655 ? C10 C2 C3 C3 -156.5(2) . . . 2_655 ? N1 C2 C3 C4 -173.6(2) . . . . ? C10 C2 C3 C4 17.4(3) . . . . ? C2 C3 C4 C5 19.4(4) . . . . ? C3 C3 C4 C5 -166.3(2) 2_655 . . . ? C2 C3 C4 C9 -166.5(2) . . . . ? C3 C3 C4 C9 7.9(2) 2_655 . . . ? C9 C4 C5 C6 4.0(3) . . . . ? C3 C4 C5 C6 177.5(2) . . . . ? C9 C4 C5 C16 -173.31(19) . . . . ? C3 C4 C5 C16 0.2(4) . . . . ? C4 C5 C6 C7 0.8(4) . . . . ? C16 C5 C6 C7 178.3(3) . . . . ? C5 C6 C7 C8 -2.4(4) . . . . ? C6 C7 C8 C7 179.2(3) . . . 2_655 ? C6 C7 C8 C9 -0.8(3) . . . . ? C7 C8 C9 C4 5.79(16) . . . . ? C7 C8 C9 C4 -174.21(16) 2_655 . . . ? C7 C8 C9 C4 -174.21(16) . . . 2_655 ? C7 C8 C9 C4 5.79(16) 2_655 . . 2_655 ? C5 C4 C9 C8 -7.6(2) . . . . ? C3 C4 C9 C8 177.11(9) . . . . ? C5 C4 C9 C4 172.4(2) . . . 2_655 ? C3 C4 C9 C4 -2.88(9) . . . 2_655 ? N1 C2 C10 C15 -115.4(2) . . . . ? C3 C2 C10 C15 54.1(3) . . . . ? N1 C2 C10 C11 63.9(3) . . . . ? C3 C2 C10 C11 -126.6(2) . . . . ? C15 C10 C11 O1 -174.20(18) . . . . ? C2 C10 C11 O1 6.5(3) . . . . ? C15 C10 C11 C12 2.1(3) . . . . ? C2 C10 C11 C12 -177.22(19) . . . . ? O1 C11 C12 C13 174.3(2) . . . . ? C10 C11 C12 C13 -1.8(3) . . . . ? C11 C12 C13 C14 0.0(4) . . . . ? C12 C13 C14 C15 1.4(4) . . . . ? C13 C14 C15 C10 -1.0(4) . . . . ? C11 C10 C15 C14 -0.7(3) . . . . ? C2 C10 C15 C14 178.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1 H1 N1 0.87(3) 1.97(3) 2.837(2) 174(3) 5_665 yes # End of CIF ============================================================ # Attachment '7,10-bis(2-hydroxyphenyl)-8,9-diazafluoranthene.cif' data_SG0709 _database_code_depnum_ccdc_archive 'CCDC 710125' _audit_creation_method SHELXL-97 _audit_creation_date 07-03-01 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C26 H16 N2 O2, 0.25(C H2 Cl2)' _chemical_formula_sum 'C26.25 H16.50 Cl0.50 N2 O2' _chemical_formula_weight 409.66 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 210 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 132 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; Cl Cl 4 0.1484 0.1585 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 16 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 16 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 n 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 7 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 7.4781(1) _cell_length_b 22.6399(3) _cell_length_c 23.8830(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.0449(7) _cell_angle_gamma 90.00 _cell_volume 4012.95(9) _cell_formula_units_Z 8 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 109460 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour paleyellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1700 _exptl_absorpt_coefficient_mu 0.150 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_absorpt_correction_T_min 0.850 _exptl_absorpt_correction_T_max 0.959 _exptl_special_details ; Solvent used: dichloromethane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.636(1) Frames collected: 571 Seconds exposure per frame: 97 Degrees rotation per frame: 1.3 Crystal-Detector distance (mm): 35.6 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 86266 _diffrn_reflns_av_R_equivalents 0.0664 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 17993 _reflns_number_gt 14245 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0815P)^2^+0.1428P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom & difmap' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0092(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack & Bernardinelli (2000), ? Friedel pairs' _refine_ls_abs_structure_Flack 0.11(5) _chemical_absolute_configuration ad _refine_ls_number_reflns 17993 _refine_ls_number_parameters 1132 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1380 _refine_ls_wR_factor_gt 0.1289 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.453 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.100 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0082(3) 0.33989(8) 0.82821(8) 0.0307(4) Uani 1 1 d . . . H1 H -0.070(6) 0.373(2) 0.8352(19) 0.078(13) Uiso 1 1 d . . . O2 O 0.2387(3) 0.22916(9) 1.05204(9) 0.0456(6) Uani 1 1 d . . . H2 H 0.2659 0.2498 1.0251 0.055 Uiso 1 1 calc R . . N1 N 0.3589(3) 0.24676(9) 0.95402(10) 0.0305(5) Uani 1 1 d . . . N2 N 0.3536(3) 0.28804(10) 0.91357(10) 0.0305(5) Uani 1 1 d . . . C3 C 0.3209(3) 0.27335(12) 0.85966(12) 0.0265(6) Uani 1 1 d . . . C4 C 0.2898(3) 0.21394(11) 0.84396(11) 0.0256(5) Uani 1 1 d . . . C5 C 0.2492(3) 0.18717(12) 0.78818(12) 0.0274(6) Uani 1 1 d . . . C6 C 0.2354(4) 0.20629(13) 0.73359(12) 0.0309(6) Uani 1 1 d . . . H61 H 0.2547 0.2467 0.7255 0.037 Uiso 1 1 calc R . . C7 C 0.1920(4) 0.16531(13) 0.68913(13) 0.0373(7) Uani 1 1 d . . . H71 H 0.1891 0.1783 0.6512 0.045 Uiso 1 1 calc R . . C8 C 0.1539(4) 0.10695(13) 0.69960(12) 0.0351(7) Uani 1 1 d . . . H81 H 0.1236 0.0805 0.6690 0.042 Uiso 1 1 calc R . . C9 C 0.1598(3) 0.08630(12) 0.75593(11) 0.0274(6) Uani 1 1 d . . . C10 C 0.1139(3) 0.02901(12) 0.77385(13) 0.0318(6) Uani 1 1 d . . . H10 H 0.0799 -0.0008 0.7467 0.038 Uiso 1 1 calc R . . C11 C 0.1185(3) 0.01654(11) 0.83082(12) 0.0299(6) Uani 1 1 d . . . H11 H 0.0819 -0.0215 0.8418 0.036 Uiso 1 1 calc R . . C12 C 0.1759(3) 0.05855(12) 0.87312(12) 0.0271(6) Uani 1 1 d . . . H12 H 0.1791 0.0487 0.9119 0.033 Uiso 1 1 calc R . . C13 C 0.2273(3) 0.11424(11) 0.85727(12) 0.0253(5) Uani 1 1 d . . . C14 C 0.2847(3) 0.17049(11) 0.88613(11) 0.0255(5) Uani 1 1 d . . . C15 C 0.3270(3) 0.18889(11) 0.94250(11) 0.0257(5) Uani 1 1 d . . . C16 C 0.2118(3) 0.12673(11) 0.79842(11) 0.0253(5) Uani 1 1 d . . . C17 C 0.3144(3) 0.32219(11) 0.81795(12) 0.0275(6) Uani 1 1 d . . . C18 C 0.1573(3) 0.35494(11) 0.80359(11) 0.0251(5) Uani 1 1 d . . . C19 C 0.1531(4) 0.40000(11) 0.76410(11) 0.0272(6) Uani 1 1 d . . . H19 H 0.0465 0.4226 0.7548 0.033 Uiso 1 1 calc R . . C20 C 0.3046(4) 0.41182(12) 0.73840(12) 0.0328(6) Uani 1 1 d . . . H20 H 0.3010 0.4423 0.7109 0.039 Uiso 1 1 calc R . . C21 C 0.4614(4) 0.37996(13) 0.75207(13) 0.0365(7) Uani 1 1 d . . . H21 H 0.5650 0.3887 0.7342 0.044 Uiso 1 1 calc R . . C22 C 0.4675(4) 0.33567(12) 0.79156(13) 0.0337(6) Uani 1 1 d . . . H22 H 0.5757 0.3140 0.8011 0.040 Uiso 1 1 calc R . . C23 C 0.3352(4) 0.15103(12) 0.99298(12) 0.0297(6) Uani 1 1 d . . . C24 C 0.2858(4) 0.17247(13) 1.04441(12) 0.0336(6) Uani 1 1 d . . . C25 C 0.2778(5) 0.13350(14) 1.08964(13) 0.0443(8) Uani 1 1 d . . . H25 H 0.2351 0.1472 1.1232 0.053 Uiso 1 1 calc R . . C26 C 0.3310(5) 0.07582(14) 1.08588(14) 0.0480(9) Uani 1 1 d . . . H26 H 0.3255 0.0498 1.1169 0.058 Uiso 1 1 calc R . . C27 C 0.3929(4) 0.05521(13) 1.03693(13) 0.0417(8) Uani 1 1 d . . . H27 H 0.4344 0.0157 1.0350 0.050 Uiso 1 1 calc R . . C28 C 0.3939(4) 0.09211(12) 0.99144(13) 0.0329(6) Uani 1 1 d . . . H28 H 0.4352 0.0775 0.9580 0.039 Uiso 1 1 calc R . . O3 O 0.8948(3) -0.08936(9) 0.92929(9) 0.0329(4) Uani 1 1 d . . . H3 H 0.975(6) -0.122(2) 0.9365(18) 0.076(13) Uiso 1 1 d . . . O4 O 0.3006(3) -0.03830(10) 0.66998(9) 0.0396(5) Uani 1 1 d . . . H4 H 0.358(7) -0.053(3) 0.698(2) 0.099(18) Uiso 1 1 d . . . N31 N 0.5115(3) -0.04943(10) 0.76632(9) 0.0288(5) Uani 1 1 d . . . N32 N 0.5134(3) -0.07229(10) 0.81754(9) 0.0270(5) Uani 1 1 d . . . C33 C 0.5908(3) -0.04310(11) 0.86298(11) 0.0234(5) Uani 1 1 d . . . C34 C 0.6605(3) 0.01308(11) 0.85732(10) 0.0229(5) Uani 1 1 d . . . C35 C 0.7393(3) 0.05504(11) 0.90003(11) 0.0226(5) Uani 1 1 d . . . C36 C 0.7982(4) 0.05201(12) 0.95678(11) 0.0295(6) Uani 1 1 d . . . H36 H 0.7925 0.0161 0.9770 0.035 Uiso 1 1 calc R . . C37 C 0.8682(4) 0.10434(13) 0.98438(12) 0.0329(6) Uani 1 1 d . . . H37 H 0.9102 0.1027 1.0235 0.040 Uiso 1 1 calc R . . C38 C 0.8771(4) 0.15689(12) 0.95653(12) 0.0322(6) Uani 1 1 d . . . H38 H 0.9208 0.1912 0.9766 0.039 Uiso 1 1 calc R . . C39 C 0.8210(3) 0.16010(12) 0.89746(12) 0.0279(6) Uani 1 1 d . . . C40 C 0.8317(4) 0.21019(12) 0.86235(13) 0.0308(6) Uani 1 1 d . . . H40 H 0.8759 0.2467 0.8780 0.037 Uiso 1 1 calc R . . C41 C 0.7777(4) 0.20530(12) 0.80564(13) 0.0319(6) Uani 1 1 d . . . H41 H 0.7861 0.2392 0.7826 0.038 Uiso 1 1 calc R . . C42 C 0.7105(3) 0.15287(12) 0.77976(12) 0.0283(6) Uani 1 1 d . . . H42 H 0.6713 0.1518 0.7404 0.034 Uiso 1 1 calc R . . C43 C 0.7023(3) 0.10291(11) 0.81244(11) 0.0242(5) Uani 1 1 d . . . C44 C 0.6446(3) 0.04059(11) 0.80418(10) 0.0229(5) Uani 1 1 d . . . C45 C 0.5750(3) 0.00525(11) 0.75765(11) 0.0240(5) Uani 1 1 d . . . C46 C 0.7556(3) 0.10893(11) 0.87124(11) 0.0245(5) Uani 1 1 d . . . C47 C 0.5790(3) -0.07388(11) 0.91780(11) 0.0244(5) Uani 1 1 d . . . C48 C 0.7323(3) -0.09699(11) 0.94863(11) 0.0246(5) Uani 1 1 d . . . C49 C 0.7166(4) -0.12787(13) 0.99822(12) 0.0333(6) Uani 1 1 d . . . H49 H 0.8207 -0.1448 1.0189 0.040 Uiso 1 1 calc R . . C50 C 0.5504(4) -0.13408(13) 1.01760(12) 0.0331(6) Uani 1 1 d . . . H50 H 0.5408 -0.1552 1.0515 0.040 Uiso 1 1 calc R . . C51 C 0.3994(4) -0.10958(12) 0.98772(12) 0.0325(6) Uani 1 1 d . . . H51 H 0.2855 -0.1133 1.0012 0.039 Uiso 1 1 calc R . . C52 C 0.4141(4) -0.07952(12) 0.93794(11) 0.0286(6) Uani 1 1 d . . . H52 H 0.3098 -0.0626 0.9174 0.034 Uiso 1 1 calc R . . C53 C 0.5637(3) 0.02201(11) 0.69716(11) 0.0264(5) Uani 1 1 d . . . C54 C 0.4280(4) -0.00041(13) 0.65682(12) 0.0298(6) Uani 1 1 d . . . C55 C 0.4186(4) 0.01658(14) 0.60120(12) 0.0377(7) Uani 1 1 d . . . H55 H 0.3220 0.0031 0.5747 0.045 Uiso 1 1 calc R . . C56 C 0.5511(4) 0.05374(16) 0.58344(13) 0.0437(8) Uani 1 1 d . . . H56 H 0.5453 0.0648 0.5449 0.052 Uiso 1 1 calc R . . C57 C 0.6912(4) 0.07434(14) 0.62252(12) 0.0375(7) Uani 1 1 d . . . H57 H 0.7828 0.0989 0.6109 0.045 Uiso 1 1 calc R . . C58 C 0.6942(4) 0.05847(13) 0.67840(12) 0.0310(6) Uani 1 1 d . . . H58 H 0.7887 0.0729 0.7051 0.037 Uiso 1 1 calc R . . O5 O 0.5651(3) 0.39073(9) 0.92264(9) 0.0341(5) Uani 1 1 d . . . H5 H 0.476(6) 0.3590(19) 0.9179(17) 0.068(12) Uiso 1 1 d . . . O6 O 0.5710(3) 0.51184(9) 0.70427(9) 0.0395(5) Uani 1 1 d . . . H6 H 0.6142 0.4894 0.7305 0.047 Uiso 1 1 calc R . . N61 N 0.7896(3) 0.48726(10) 0.79950(9) 0.0278(5) Uani 1 1 d . . . N62 N 0.8210(3) 0.44564(10) 0.83964(9) 0.0278(5) Uani 1 1 d . . . C63 C 0.8439(3) 0.46156(12) 0.89434(11) 0.0256(5) Uani 1 1 d . . . C64 C 0.8335(3) 0.52027(11) 0.91001(11) 0.0243(5) Uani 1 1 d . . . C65 C 0.8424(3) 0.54809(11) 0.96616(11) 0.0266(5) Uani 1 1 d . . . C66 C 0.8845(4) 0.52879(12) 1.02151(12) 0.0305(6) Uani 1 1 d . . . H66 H 0.9169 0.4889 1.0297 0.037 Uiso 1 1 calc R . . C67 C 0.8775(4) 0.57020(14) 1.06497(12) 0.0362(7) Uani 1 1 d . . . H67 H 0.9083 0.5578 1.1029 0.043 Uiso 1 1 calc R . . C68 C 0.8279(4) 0.62781(13) 1.05469(12) 0.0342(6) Uani 1 1 d . . . H68 H 0.8242 0.6542 1.0855 0.041 Uiso 1 1 calc R . . C69 C 0.7824(3) 0.64860(12) 0.99897(12) 0.0283(6) Uani 1 1 d . . . C70 C 0.7172(4) 0.70522(13) 0.98060(12) 0.0314(6) Uani 1 1 d . . . H70 H 0.7040 0.7350 1.0078 0.038 Uiso 1 1 calc R . . C71 C 0.6732(4) 0.71773(12) 0.92457(12) 0.0304(6) Uani 1 1 d . . . H711 H 0.6270 0.7557 0.9139 0.036 Uiso 1 1 calc R . . C72 C 0.6947(3) 0.67551(12) 0.88195(12) 0.0278(6) Uani 1 1 d . . . H72 H 0.6641 0.6852 0.8433 0.033 Uiso 1 1 calc R . . C73 C 0.7608(3) 0.62011(11) 0.89738(11) 0.0255(5) Uani 1 1 d . . . C74 C 0.7894(3) 0.56373(11) 0.86835(11) 0.0240(5) Uani 1 1 d . . . C75 C 0.7757(3) 0.54498(11) 0.81224(11) 0.0254(5) Uani 1 1 d . . . C76 C 0.7988(3) 0.60784(11) 0.95621(11) 0.0256(5) Uani 1 1 d . . . C77 C 0.8761(4) 0.41276(11) 0.93631(11) 0.0280(6) Uani 1 1 d . . . C78 C 0.7312(3) 0.37727(11) 0.94862(11) 0.0261(5) Uani 1 1 d . . . C79 C 0.7623(4) 0.33222(12) 0.98811(12) 0.0321(6) Uani 1 1 d . . . H79 H 0.6652 0.3079 0.9963 0.039 Uiso 1 1 calc R . . C80 C 0.9337(4) 0.32250(13) 1.01572(12) 0.0351(7) Uani 1 1 d . . . H80 H 0.9540 0.2917 1.0428 0.042 Uiso 1 1 calc R . . C81 C 1.0745(4) 0.35760(13) 1.00383(13) 0.0347(6) Uani 1 1 d . . . H811 H 1.1912 0.3515 1.0236 0.042 Uiso 1 1 calc R . . C82 C 1.0483(4) 0.40107(13) 0.96395(12) 0.0332(6) Uani 1 1 d . . . H82 H 1.1481 0.4236 0.9549 0.040 Uiso 1 1 calc R . . C83 C 0.7477(3) 0.58424(12) 0.76179(11) 0.0264(6) Uani 1 1 d . . . C84 C 0.6497(4) 0.56594(12) 0.71108(12) 0.0306(6) Uani 1 1 d . . . C85 C 0.6236(4) 0.60434(14) 0.66504(13) 0.0395(7) Uani 1 1 d . . . H85 H 0.5540 0.5920 0.6311 0.047 Uiso 1 1 calc R . . C86 C 0.6983(4) 0.66012(13) 0.66865(13) 0.0400(7) Uani 1 1 d . . . H86 H 0.6785 0.6862 0.6373 0.048 Uiso 1 1 calc R . . C87 C 0.8017(4) 0.67832(13) 0.71737(13) 0.0371(7) Uani 1 1 d . . . H87 H 0.8562 0.7163 0.7194 0.044 Uiso 1 1 calc R . . C88 C 0.8251(4) 0.64051(12) 0.76350(12) 0.0305(6) Uani 1 1 d . . . H88 H 0.8956 0.6532 0.7971 0.037 Uiso 1 1 calc R . . O7 O 0.3763(3) 0.81639(10) 0.83491(9) 0.0388(5) Uani 1 1 d . . . H7 H 0.441(5) 0.8456(16) 0.8327(14) 0.040(9) Uiso 1 1 d . . . O8 O -0.0236(3) 0.77192(9) 1.09465(8) 0.0349(5) Uani 1 1 d . . . H8 H -0.0242 0.7871 1.0625 0.042 Uiso 1 1 calc R . . N91 N 0.0993(3) 0.78372(9) 0.99517(9) 0.0252(5) Uani 1 1 d . . . N92 N 0.0615(3) 0.80468(10) 0.94255(9) 0.0259(5) Uani 1 1 d . . . C93 C 0.1120(3) 0.77507(11) 0.89873(10) 0.0248(5) Uani 1 1 d . . . C94 C 0.1919(3) 0.71965(11) 0.90627(11) 0.0236(5) Uani 1 1 d . . . C95 C 0.2382(3) 0.67504(12) 0.86574(11) 0.0281(6) Uani 1 1 d . . . C96 C 0.2503(4) 0.67386(13) 0.80897(12) 0.0337(6) Uani 1 1 d . . . H96 H 0.2278 0.7084 0.7866 0.040 Uiso 1 1 calc R . . C97 C 0.2970(4) 0.62025(15) 0.78453(14) 0.0406(8) Uani 1 1 d . . . H97 H 0.3054 0.6191 0.7452 0.049 Uiso 1 1 calc R . . C98 C 0.3308(4) 0.56956(14) 0.81556(14) 0.0408(8) Uani 1 1 d . . . H98 H 0.3561 0.5339 0.7972 0.049 Uiso 1 1 calc R . . C99 C 0.3283(3) 0.56999(13) 0.87444(14) 0.0350(7) Uani 1 1 d . . . C100 C 0.3677(4) 0.52308(13) 0.91292(16) 0.0410(8) Uani 1 1 d . . . H100 H 0.3989 0.4854 0.8995 0.049 Uiso 1 1 calc R . . C101 C 0.3614(4) 0.53156(13) 0.96957(15) 0.0403(7) Uani 1 1 d . . . H101 H 0.3890 0.4992 0.9945 0.048 Uiso 1 1 calc R . . C102 C 0.3151(4) 0.58673(12) 0.99250(14) 0.0333(6) Uani 1 1 d . . . H102 H 0.3105 0.5911 1.0319 0.040 Uiso 1 1 calc R . . C103 C 0.2773(3) 0.63328(11) 0.95661(12) 0.0270(6) Uani 1 1 d . . . C104 C 0.2205(3) 0.69545(11) 0.96098(11) 0.0241(5) Uani 1 1 d . . . C105 C 0.1837(3) 0.73198(11) 1.00603(11) 0.0224(5) Uani 1 1 d . . . C106 C 0.2831(3) 0.62402(12) 0.89799(12) 0.0281(6) Uani 1 1 d . . . C107 C 0.0659(4) 0.80432(12) 0.84278(11) 0.0289(6) Uani 1 1 d . . . C108 C 0.2011(4) 0.82405(12) 0.81300(12) 0.0336(6) Uani 1 1 d . . . C109 C 0.1565(5) 0.85305(15) 0.76145(13) 0.0482(9) Uani 1 1 d . . . H109 H 0.2491 0.8666 0.7407 0.058 Uiso 1 1 calc R . . C110 C -0.0211(5) 0.86185(15) 0.74082(14) 0.0506(9) Uani 1 1 d . . . H110 H -0.0497 0.8815 0.7057 0.061 Uiso 1 1 calc R . . C111 C -0.1602(5) 0.84272(15) 0.77008(13) 0.0428(7) Uani 1 1 d . . . H111 H -0.2827 0.8494 0.7557 0.051 Uiso 1 1 calc R . . C112 C -0.1138(4) 0.81324(13) 0.82161(12) 0.0348(6) Uani 1 1 d . . . H112 H -0.2062 0.7993 0.8422 0.042 Uiso 1 1 calc R . . C113 C 0.2342(3) 0.71893(11) 1.06663(11) 0.0264(6) Uani 1 1 d . . . C114 C 0.1271(3) 0.73903(12) 1.10689(11) 0.0275(6) Uani 1 1 d . . . C115 C 0.1758(4) 0.72508(13) 1.16444(11) 0.0327(6) Uani 1 1 d . . . H115 H 0.1025 0.7378 1.1919 0.039 Uiso 1 1 calc R . . C116 C 0.3294(4) 0.69307(14) 1.18035(12) 0.0369(7) Uani 1 1 d . . . H116 H 0.3598 0.6827 1.2189 0.044 Uiso 1 1 calc R . . C117 C 0.4400(4) 0.67583(13) 1.14133(12) 0.0337(6) Uani 1 1 d . . . H117 H 0.5487 0.6552 1.1532 0.040 Uiso 1 1 calc R . . C118 C 0.3932(4) 0.68847(12) 1.08552(12) 0.0297(6) Uani 1 1 d . . . H118 H 0.4703 0.6763 1.0589 0.036 Uiso 1 1 calc R . . Cl1 Cl 0.45277(14) 0.51591(4) 1.13547(4) 0.0574(2) Uani 1 1 d . . . Cl2 Cl 0.60107(18) 0.41219(5) 1.08669(5) 0.0779(3) Uani 1 1 d . . . C119 C 0.5723(5) 0.44850(16) 1.14895(16) 0.0568(9) Uani 1 1 d . . . H119 H 0.6917 0.4568 1.1703 0.068 Uiso 1 1 calc R . . H120 H 0.5051 0.4227 1.1725 0.068 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0331(10) 0.0260(10) 0.0345(11) 0.0030(8) 0.0102(8) 0.0002(8) O2 0.0761(16) 0.0334(11) 0.0264(11) 0.0007(9) 0.0034(11) 0.0123(11) N1 0.0369(12) 0.0205(11) 0.0327(13) -0.0013(9) -0.0017(10) -0.0022(9) N2 0.0345(12) 0.0246(11) 0.0318(13) 0.0017(10) 0.0012(10) -0.0009(10) C3 0.0236(12) 0.0229(13) 0.0328(15) 0.0008(11) 0.0029(11) 0.0017(10) C4 0.0192(11) 0.0259(13) 0.0313(14) 0.0022(11) 0.0018(10) -0.0005(10) C5 0.0222(12) 0.0273(13) 0.0323(15) 0.0034(11) 0.0020(10) -0.0013(10) C6 0.0308(14) 0.0312(14) 0.0305(15) 0.0038(12) 0.0030(11) -0.0038(11) C7 0.0436(16) 0.0366(17) 0.0313(16) 0.0036(13) 0.0034(13) -0.0017(13) C8 0.0329(15) 0.0411(17) 0.0308(16) -0.0073(13) 0.0016(12) -0.0017(13) C9 0.0226(12) 0.0297(14) 0.0300(15) -0.0051(11) 0.0030(10) 0.0015(11) C10 0.0261(13) 0.0260(14) 0.0417(17) -0.0075(12) -0.0018(11) 0.0026(11) C11 0.0261(13) 0.0190(12) 0.0434(17) 0.0022(12) -0.0015(11) 0.0033(10) C12 0.0229(12) 0.0266(14) 0.0316(15) 0.0009(11) 0.0026(10) 0.0022(10) C13 0.0191(11) 0.0232(13) 0.0330(15) 0.0011(11) 0.0012(10) 0.0051(10) C14 0.0175(11) 0.0282(13) 0.0306(15) -0.0006(11) 0.0018(10) 0.0028(10) C15 0.0233(12) 0.0218(13) 0.0314(15) 0.0036(11) 0.0011(10) 0.0024(10) C16 0.0209(11) 0.0229(12) 0.0319(15) -0.0004(11) 0.0030(10) 0.0021(10) C17 0.0318(14) 0.0192(12) 0.0314(15) -0.0026(11) 0.0042(11) -0.0009(10) C18 0.0257(12) 0.0237(13) 0.0256(14) -0.0049(11) 0.0023(10) -0.0030(10) C19 0.0320(13) 0.0241(13) 0.0246(14) -0.0032(11) 0.0003(10) -0.0029(11) C20 0.0439(16) 0.0236(13) 0.0310(15) 0.0030(11) 0.0055(12) -0.0036(12) C21 0.0362(15) 0.0320(15) 0.0438(18) 0.0014(13) 0.0149(13) -0.0066(12) C22 0.0337(14) 0.0265(14) 0.0423(17) 0.0005(12) 0.0102(12) 0.0044(11) C23 0.0319(14) 0.0273(14) 0.0281(14) 0.0012(11) -0.0033(11) -0.0039(11) C24 0.0421(16) 0.0298(15) 0.0266(15) 0.0013(12) -0.0052(12) 0.0062(12) C25 0.064(2) 0.0417(18) 0.0255(16) 0.0006(14) -0.0019(14) 0.0009(15) C26 0.078(2) 0.0329(16) 0.0282(16) 0.0091(14) -0.0133(16) -0.0034(16) C27 0.0562(19) 0.0243(14) 0.0394(18) 0.0030(13) -0.0153(15) 0.0022(13) C28 0.0334(14) 0.0284(14) 0.0347(16) -0.0011(12) -0.0045(12) 0.0075(12) O3 0.0306(10) 0.0286(10) 0.0400(12) 0.0083(9) 0.0068(8) 0.0056(8) O4 0.0437(12) 0.0467(13) 0.0256(11) 0.0016(10) -0.0071(9) -0.0125(10) N31 0.0322(11) 0.0298(12) 0.0237(12) 0.0035(10) 0.0004(9) -0.0057(10) N32 0.0315(11) 0.0278(12) 0.0206(11) 0.0014(9) -0.0010(9) -0.0018(9) C33 0.0222(12) 0.0239(13) 0.0238(13) 0.0000(10) 0.0012(10) 0.0041(10) C34 0.0193(11) 0.0269(13) 0.0218(13) 0.0020(10) 0.0001(9) 0.0030(10) C35 0.0220(12) 0.0195(12) 0.0262(13) -0.0004(10) 0.0020(10) 0.0006(9) C36 0.0332(14) 0.0312(14) 0.0235(14) 0.0013(11) 0.0016(11) -0.0015(11) C37 0.0359(15) 0.0373(16) 0.0242(14) -0.0059(12) -0.0019(11) -0.0050(12) C38 0.0329(14) 0.0284(14) 0.0349(16) -0.0091(12) 0.0021(12) -0.0016(11) C39 0.0241(12) 0.0265(14) 0.0333(15) -0.0002(11) 0.0048(11) 0.0009(10) C40 0.0279(13) 0.0223(13) 0.0420(17) -0.0004(12) 0.0036(12) 0.0022(11) C41 0.0319(14) 0.0219(13) 0.0430(17) 0.0114(12) 0.0093(12) 0.0043(11) C42 0.0280(13) 0.0276(14) 0.0297(15) 0.0045(11) 0.0053(11) 0.0027(11) C43 0.0218(12) 0.0282(13) 0.0229(13) 0.0015(11) 0.0038(10) 0.0036(10) C44 0.0209(11) 0.0249(13) 0.0226(13) 0.0026(10) 0.0016(10) 0.0027(10) C45 0.0266(12) 0.0219(12) 0.0227(13) 0.0010(10) 0.0000(10) 0.0045(10) C46 0.0200(11) 0.0260(13) 0.0282(14) 0.0016(11) 0.0057(10) 0.0013(10) C47 0.0303(13) 0.0200(12) 0.0223(13) -0.0016(10) 0.0015(10) -0.0020(10) C48 0.0300(13) 0.0176(12) 0.0254(14) 0.0011(10) -0.0003(10) 0.0008(10) C49 0.0410(16) 0.0281(14) 0.0295(15) 0.0055(12) -0.0016(12) 0.0050(12) C50 0.0495(17) 0.0292(15) 0.0209(14) 0.0043(11) 0.0061(12) 0.0020(13) C51 0.0409(15) 0.0327(15) 0.0249(14) -0.0007(12) 0.0083(12) -0.0014(12) C52 0.0350(14) 0.0279(14) 0.0233(14) 0.0019(11) 0.0050(11) 0.0020(11) C53 0.0301(13) 0.0276(13) 0.0210(13) 0.0054(11) 0.0012(10) 0.0058(11) C54 0.0279(13) 0.0335(15) 0.0285(15) 0.0019(12) 0.0048(11) 0.0021(11) C55 0.0411(16) 0.0487(18) 0.0218(15) -0.0027(13) -0.0018(12) 0.0019(14) C56 0.0482(18) 0.060(2) 0.0221(15) 0.0087(14) 0.0003(13) 0.0049(16) C57 0.0378(15) 0.0464(18) 0.0289(15) 0.0094(13) 0.0069(12) 0.0009(13) C58 0.0302(13) 0.0366(15) 0.0267(15) 0.0032(12) 0.0058(11) 0.0032(12) O5 0.0304(10) 0.0253(10) 0.0445(12) 0.0068(9) -0.0040(9) -0.0030(8) O6 0.0522(12) 0.0351(11) 0.0292(11) 0.0034(9) -0.0029(9) -0.0142(10) N61 0.0307(11) 0.0260(12) 0.0264(12) 0.0018(9) 0.0025(9) 0.0009(9) N62 0.0307(11) 0.0253(11) 0.0273(12) 0.0016(10) 0.0027(9) -0.0012(9) C63 0.0264(13) 0.0253(13) 0.0253(14) 0.0009(11) 0.0040(10) -0.0015(10) C64 0.0214(12) 0.0267(13) 0.0248(13) 0.0029(11) 0.0033(10) 0.0004(10) C65 0.0259(12) 0.0254(13) 0.0290(14) -0.0015(11) 0.0050(10) -0.0020(10) C66 0.0336(14) 0.0299(14) 0.0283(14) 0.0039(12) 0.0050(11) -0.0005(12) C67 0.0387(15) 0.0449(18) 0.0242(15) -0.0004(13) 0.0010(12) -0.0016(13) C68 0.0333(14) 0.0383(16) 0.0320(16) -0.0049(13) 0.0076(12) -0.0059(12) C69 0.0234(12) 0.0305(14) 0.0316(15) 0.0003(12) 0.0054(11) -0.0020(11) C70 0.0347(14) 0.0285(14) 0.0323(16) -0.0084(12) 0.0094(12) -0.0041(11) C71 0.0279(13) 0.0218(13) 0.0417(17) 0.0020(12) 0.0055(12) -0.0013(10) C72 0.0275(13) 0.0255(14) 0.0296(15) 0.0008(11) 0.0006(11) -0.0042(11) C73 0.0226(12) 0.0242(13) 0.0298(14) 0.0000(11) 0.0032(10) -0.0050(10) C74 0.0215(12) 0.0239(13) 0.0273(14) 0.0016(11) 0.0054(10) -0.0026(10) C75 0.0217(12) 0.0248(13) 0.0295(14) 0.0021(11) 0.0032(10) -0.0044(10) C76 0.0234(12) 0.0270(13) 0.0262(14) -0.0003(11) 0.0021(10) -0.0023(10) C77 0.0345(14) 0.0218(13) 0.0267(14) -0.0007(11) -0.0005(11) 0.0005(11) C78 0.0304(13) 0.0233(13) 0.0242(13) -0.0016(11) 0.0017(10) 0.0015(10) C79 0.0352(15) 0.0301(15) 0.0314(15) 0.0023(12) 0.0057(12) -0.0041(12) C80 0.0436(16) 0.0294(14) 0.0305(16) 0.0036(12) -0.0022(13) 0.0079(13) C81 0.0358(15) 0.0293(15) 0.0368(17) -0.0016(13) -0.0046(12) 0.0028(12) C82 0.0316(14) 0.0334(15) 0.0337(16) -0.0022(12) 0.0004(12) -0.0022(12) C83 0.0282(13) 0.0266(13) 0.0249(14) 0.0037(11) 0.0058(10) -0.0018(11) C84 0.0334(14) 0.0280(14) 0.0309(15) 0.0022(12) 0.0060(11) -0.0040(11) C85 0.0439(17) 0.0457(18) 0.0276(16) 0.0013(14) -0.0013(13) -0.0038(14) C86 0.0554(18) 0.0328(16) 0.0319(16) 0.0117(13) 0.0062(14) -0.0011(14) C87 0.0520(18) 0.0281(14) 0.0324(16) 0.0072(12) 0.0104(13) -0.0057(13) C88 0.0334(14) 0.0321(15) 0.0260(14) -0.0030(12) 0.0042(11) -0.0056(11) O7 0.0452(12) 0.0380(12) 0.0330(12) 0.0032(9) 0.0042(9) -0.0143(10) O8 0.0378(10) 0.0440(12) 0.0235(10) 0.0032(9) 0.0058(8) 0.0169(9) N91 0.0318(11) 0.0236(11) 0.0201(11) 0.0038(9) 0.0028(9) 0.0019(9) N92 0.0321(11) 0.0231(11) 0.0220(11) 0.0022(9) 0.0016(9) 0.0020(9) C93 0.0288(13) 0.0267(13) 0.0192(13) 0.0007(11) 0.0038(10) -0.0015(11) C94 0.0232(12) 0.0229(13) 0.0247(13) -0.0003(10) 0.0025(10) -0.0021(10) C95 0.0249(13) 0.0325(15) 0.0266(14) -0.0059(11) 0.0024(10) -0.0013(11) C96 0.0292(13) 0.0397(16) 0.0320(15) -0.0053(13) 0.0030(11) -0.0036(12) C97 0.0317(15) 0.053(2) 0.0370(17) -0.0201(15) 0.0052(13) -0.0016(14) C98 0.0292(14) 0.0384(17) 0.055(2) -0.0230(15) 0.0060(13) -0.0030(13) C99 0.0226(13) 0.0299(15) 0.0533(19) -0.0094(14) 0.0081(12) -0.0050(11) C100 0.0278(14) 0.0245(14) 0.071(2) -0.0074(15) 0.0077(14) -0.0013(12) C101 0.0305(15) 0.0266(14) 0.065(2) 0.0056(15) 0.0091(14) 0.0023(12) C102 0.0293(14) 0.0248(14) 0.0460(18) 0.0083(12) 0.0063(12) 0.0001(11) C103 0.0222(12) 0.0254(13) 0.0338(15) 0.0009(11) 0.0047(10) -0.0020(10) C104 0.0221(12) 0.0216(12) 0.0289(14) 0.0048(11) 0.0049(10) -0.0011(10) C105 0.0249(12) 0.0219(12) 0.0204(12) 0.0032(10) 0.0031(10) -0.0013(10) C106 0.0228(12) 0.0247(13) 0.0370(16) -0.0052(12) 0.0050(11) -0.0038(10) C107 0.0423(15) 0.0238(13) 0.0199(13) 0.0013(11) 0.0006(11) -0.0032(12) C108 0.0453(16) 0.0274(14) 0.0271(15) 0.0015(12) 0.0006(12) -0.0088(12) C109 0.067(2) 0.0499(19) 0.0256(16) 0.0069(14) -0.0043(15) -0.0310(17) C110 0.079(2) 0.0414(19) 0.0259(16) 0.0065(14) -0.0168(16) -0.0167(17) C111 0.0539(19) 0.0435(18) 0.0273(16) 0.0050(13) -0.0095(14) 0.0062(15) C112 0.0380(15) 0.0366(16) 0.0286(15) 0.0004(12) 0.0002(12) 0.0031(12) C113 0.0279(13) 0.0254(13) 0.0257(14) 0.0038(11) 0.0022(10) 0.0023(10) C114 0.0285(13) 0.0278(14) 0.0251(14) 0.0020(11) -0.0002(11) 0.0017(11) C115 0.0420(15) 0.0385(16) 0.0182(13) 0.0011(12) 0.0056(11) 0.0067(13) C116 0.0439(16) 0.0438(17) 0.0223(14) 0.0073(12) 0.0010(12) 0.0071(13) C117 0.0326(14) 0.0371(15) 0.0306(15) 0.0059(12) 0.0009(12) 0.0054(12) C118 0.0283(13) 0.0308(14) 0.0299(15) 0.0030(12) 0.0027(11) 0.0023(11) Cl1 0.0771(6) 0.0442(5) 0.0518(5) 0.0014(4) 0.0113(4) 0.0057(4) Cl2 0.1058(8) 0.0555(6) 0.0787(7) -0.0077(5) 0.0362(6) 0.0095(6) C119 0.068(2) 0.047(2) 0.056(2) 0.0106(18) 0.0051(18) 0.0044(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C18 1.366(3) . ? O1 H1 0.97(5) . ? O2 C24 1.349(3) . ? O2 H2 0.8400 . ? N1 N2 1.341(3) . ? N1 C15 1.354(3) . ? N2 C3 1.323(4) . ? C3 C4 1.408(4) . ? C3 C17 1.485(4) . ? C4 C14 1.412(4) . ? C4 C5 1.461(4) . ? C5 C6 1.366(4) . ? C5 C16 1.424(4) . ? C6 C7 1.417(4) . ? C6 H61 0.9500 . ? C7 C8 1.381(4) . ? C7 H71 0.9500 . ? C8 C9 1.420(4) . ? C8 H81 0.9500 . ? C9 C16 1.386(4) . ? C9 C10 1.421(4) . ? C10 C11 1.386(4) . ? C10 H10 0.9500 . ? C11 C12 1.415(4) . ? C11 H11 0.9500 . ? C12 C13 1.384(4) . ? C12 H12 0.9500 . ? C13 C16 1.425(4) . ? C13 C14 1.486(4) . ? C14 C15 1.408(4) . ? C15 C23 1.474(4) . ? C17 C18 1.396(4) . ? C17 C22 1.406(4) . ? C18 C19 1.387(4) . ? C19 C20 1.380(4) . ? C19 H19 0.9500 . ? C20 C21 1.381(4) . ? C20 H20 0.9500 . ? C21 C22 1.374(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C28 1.406(4) . ? C23 C24 1.412(4) . ? C24 C25 1.402(4) . ? C25 C26 1.371(5) . ? C25 H25 0.9500 . ? C26 C27 1.390(5) . ? C26 H26 0.9500 . ? C27 C28 1.371(4) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? O3 C48 1.363(3) . ? O3 H3 0.96(5) . ? O4 C54 1.347(3) . ? O4 H4 0.82(5) . ? N31 N32 1.327(3) . ? N31 C45 1.351(3) . ? N32 C33 1.340(3) . ? C33 C34 1.388(4) . ? C33 C47 1.495(4) . ? C34 C44 1.405(3) . ? C34 C35 1.464(4) . ? C35 C36 1.375(4) . ? C35 C46 1.413(4) . ? C36 C37 1.424(4) . ? C36 H36 0.9500 . ? C37 C38 1.369(4) . ? C37 H37 0.9500 . ? C38 C39 1.423(4) . ? C38 H38 0.9500 . ? C39 C46 1.378(4) . ? C39 C40 1.419(4) . ? C40 C41 1.370(4) . ? C40 H40 0.9500 . ? C41 C42 1.403(4) . ? C41 H41 0.9500 . ? C42 C43 1.380(4) . ? C42 H42 0.9500 . ? C43 C46 1.418(4) . ? C43 C44 1.482(4) . ? C44 C45 1.416(4) . ? C45 C53 1.486(4) . ? C47 C52 1.384(4) . ? C47 C48 1.386(4) . ? C48 C49 1.392(4) . ? C49 C50 1.385(4) . ? C49 H49 0.9500 . ? C50 C51 1.377(4) . ? C50 H50 0.9500 . ? C51 C52 1.386(4) . ? C51 H51 0.9500 . ? C52 H52 0.9500 . ? C53 C58 1.393(4) . ? C53 C54 1.406(4) . ? C54 C55 1.376(4) . ? C55 C56 1.404(5) . ? C55 H55 0.9500 . ? C56 C57 1.395(4) . ? C56 H56 0.9500 . ? C57 C58 1.380(4) . ? C57 H57 0.9500 . ? C58 H58 0.9500 . ? O5 C78 1.353(3) . ? O5 H5 0.98(5) . ? O6 C84 1.360(3) . ? O6 H6 0.8400 . ? N61 N62 1.344(3) . ? N61 C75 1.348(4) . ? N62 C63 1.346(3) . ? C63 C64 1.386(4) . ? C63 C77 1.491(4) . ? C64 C74 1.409(4) . ? C64 C65 1.476(4) . ? C65 C66 1.391(4) . ? C65 C76 1.405(4) . ? C66 C67 1.404(4) . ? C66 H66 0.9500 . ? C67 C68 1.370(4) . ? C67 H67 0.9500 . ? C68 C69 1.413(4) . ? C68 H68 0.9500 . ? C69 C76 1.393(4) . ? C69 C70 1.422(4) . ? C70 C71 1.368(4) . ? C70 H70 0.9500 . ? C71 C72 1.420(4) . ? C71 H711 0.9500 . ? C72 C73 1.381(4) . ? C72 H72 0.9500 . ? C73 C76 1.426(4) . ? C73 C74 1.481(4) . ? C74 C75 1.397(4) . ? C75 C83 1.491(4) . ? C77 C82 1.398(4) . ? C77 C78 1.409(4) . ? C78 C79 1.389(4) . ? C79 C80 1.385(4) . ? C79 H79 0.9500 . ? C80 C81 1.376(4) . ? C80 H80 0.9500 . ? C81 C82 1.367(4) . ? C81 H811 0.9500 . ? C82 H82 0.9500 . ? C83 C88 1.398(4) . ? C83 C84 1.399(4) . ? C84 C85 1.397(4) . ? C85 C86 1.380(4) . ? C85 H85 0.9500 . ? C86 C87 1.378(4) . ? C86 H86 0.9500 . ? C87 C88 1.389(4) . ? C87 H87 0.9500 . ? C88 H88 0.9500 . ? O7 C108 1.361(4) . ? O7 H7 0.82(4) . ? O8 C114 1.352(3) . ? O8 H8 0.8400 . ? N91 N92 1.341(3) . ? N91 C105 1.341(3) . ? N92 C93 1.336(3) . ? C93 C94 1.392(4) . ? C93 C107 1.493(4) . ? C94 C104 1.409(4) . ? C94 C95 1.469(4) . ? C95 C96 1.370(4) . ? C95 C106 1.406(4) . ? C96 C97 1.409(4) . ? C96 H96 0.9500 . ? C97 C98 1.373(5) . ? C97 H97 0.9500 . ? C98 C99 1.408(5) . ? C98 H98 0.9500 . ? C99 C106 1.405(4) . ? C99 C100 1.412(5) . ? C100 C101 1.373(5) . ? C100 H100 0.9500 . ? C101 C102 1.424(4) . ? C101 H101 0.9500 . ? C102 C103 1.366(4) . ? C102 H102 0.9500 . ? C103 C106 1.422(4) . ? C103 C104 1.477(4) . ? C104 C105 1.411(4) . ? C105 C113 1.480(4) . ? C107 C108 1.379(4) . ? C107 C112 1.391(4) . ? C108 C109 1.399(4) . ? C109 C110 1.373(5) . ? C109 H109 0.9500 . ? C110 C111 1.391(5) . ? C110 H110 0.9500 . ? C111 C112 1.406(4) . ? C111 H111 0.9500 . ? C112 H112 0.9500 . ? C113 C118 1.400(4) . ? C113 C114 1.401(4) . ? C114 C115 1.414(4) . ? C115 C116 1.372(4) . ? C115 H115 0.9500 . ? C116 C117 1.377(4) . ? C116 H116 0.9500 . ? C117 C118 1.366(4) . ? C117 H117 0.9500 . ? C118 H118 0.9500 . ? Cl1 C119 1.778(4) . ? Cl2 C119 1.735(4) . ? C119 H119 0.9900 . ? C119 H120 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C18 O1 H1 115(3) . . ? C24 O2 H2 109.5 . . ? N2 N1 C15 122.6(2) . . ? C3 N2 N1 120.8(2) . . ? N2 C3 C4 120.3(2) . . ? N2 C3 C17 116.9(2) . . ? C4 C3 C17 122.8(2) . . ? C3 C4 C14 119.6(2) . . ? C3 C4 C5 130.4(2) . . ? C14 C4 C5 109.9(2) . . ? C6 C5 C16 118.4(3) . . ? C6 C5 C4 136.2(3) . . ? C16 C5 C4 105.4(2) . . ? C5 C6 C7 119.4(3) . . ? C5 C6 H61 120.3 . . ? C7 C6 H61 120.3 . . ? C8 C7 C6 121.6(3) . . ? C8 C7 H71 119.2 . . ? C6 C7 H71 119.2 . . ? C7 C8 C9 120.2(3) . . ? C7 C8 H81 119.9 . . ? C9 C8 H81 119.9 . . ? C16 C9 C8 116.7(2) . . ? C16 C9 C10 116.0(2) . . ? C8 C9 C10 127.2(3) . . ? C11 C10 C9 120.3(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 122.2(2) . . ? C10 C11 H11 118.9 . . ? C12 C11 H11 118.9 . . ? C13 C12 C11 119.1(3) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C16 117.3(2) . . ? C12 C13 C14 136.7(3) . . ? C16 C13 C14 105.7(2) . . ? C15 C14 C4 117.0(2) . . ? C15 C14 C13 135.7(2) . . ? C4 C14 C13 107.3(2) . . ? N1 C15 C14 119.6(2) . . ? N1 C15 C23 114.1(2) . . ? C14 C15 C23 126.3(2) . . ? C9 C16 C5 123.5(2) . . ? C9 C16 C13 124.9(2) . . ? C5 C16 C13 111.5(2) . . ? C18 C17 C22 118.8(2) . . ? C18 C17 C3 121.2(2) . . ? C22 C17 C3 120.0(2) . . ? O1 C18 C19 121.6(2) . . ? O1 C18 C17 117.9(2) . . ? C19 C18 C17 120.4(2) . . ? C20 C19 C18 119.6(3) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C19 C20 C21 120.9(3) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C22 C21 C20 119.9(3) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C17 120.4(3) . . ? C21 C22 H22 119.8 . . ? C17 C22 H22 119.8 . . ? C28 C23 C24 117.7(3) . . ? C28 C23 C15 120.8(3) . . ? C24 C23 C15 121.5(2) . . ? O2 C24 C25 117.3(3) . . ? O2 C24 C23 123.0(3) . . ? C25 C24 C23 119.7(3) . . ? C26 C25 C24 120.6(3) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C27 120.3(3) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C28 C27 C26 119.8(3) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C27 C28 C23 121.7(3) . . ? C27 C28 H28 119.2 . . ? C23 C28 H28 119.2 . . ? C48 O3 H3 114(3) . . ? C54 O4 H4 98(4) . . ? N32 N31 C45 122.3(2) . . ? N31 N32 C33 120.6(2) . . ? N32 C33 C34 120.2(2) . . ? N32 C33 C47 114.4(2) . . ? C34 C33 C47 125.1(2) . . ? C33 C34 C44 120.2(2) . . ? C33 C34 C35 130.6(2) . . ? C44 C34 C35 108.9(2) . . ? C36 C35 C46 119.1(2) . . ? C36 C35 C34 135.1(2) . . ? C46 C35 C34 105.8(2) . . ? C35 C36 C37 118.1(3) . . ? C35 C36 H36 121.0 . . ? C37 C36 H36 121.0 . . ? C38 C37 C36 122.4(3) . . ? C38 C37 H37 118.8 . . ? C36 C37 H37 118.8 . . ? C37 C38 C39 120.0(3) . . ? C37 C38 H38 120.0 . . ? C39 C38 H38 120.0 . . ? C46 C39 C40 116.5(2) . . ? C46 C39 C38 116.9(2) . . ? C40 C39 C38 126.5(3) . . ? C41 C40 C39 119.3(3) . . ? C41 C40 H40 120.4 . . ? C39 C40 H40 120.4 . . ? C40 C41 C42 123.4(2) . . ? C40 C41 H41 118.3 . . ? C42 C41 H41 118.3 . . ? C43 C42 C41 118.9(3) . . ? C43 C42 H42 120.6 . . ? C41 C42 H42 120.6 . . ? C42 C43 C46 117.1(2) . . ? C42 C43 C44 137.5(2) . . ? C46 C43 C44 105.4(2) . . ? C34 C44 C45 116.1(2) . . ? C34 C44 C43 108.1(2) . . ? C45 C44 C43 135.7(2) . . ? N31 C45 C44 120.0(2) . . ? N31 C45 C53 113.8(2) . . ? C44 C45 C53 126.2(2) . . ? C39 C46 C35 123.5(2) . . ? C39 C46 C43 124.9(2) . . ? C35 C46 C43 111.6(2) . . ? C52 C47 C48 119.6(2) . . ? C52 C47 C33 119.9(2) . . ? C48 C47 C33 120.5(2) . . ? O3 C48 C47 119.0(2) . . ? O3 C48 C49 121.6(2) . . ? C47 C48 C49 119.4(2) . . ? C50 C49 C48 120.5(3) . . ? C50 C49 H49 119.8 . . ? C48 C49 H49 119.8 . . ? C51 C50 C49 119.9(3) . . ? C51 C50 H50 120.0 . . ? C49 C50 H50 120.0 . . ? C50 C51 C52 119.7(3) . . ? C50 C51 H51 120.1 . . ? C52 C51 H51 120.1 . . ? C47 C52 C51 120.8(3) . . ? C47 C52 H52 119.6 . . ? C51 C52 H52 119.6 . . ? C58 C53 C54 117.9(2) . . ? C58 C53 C45 120.4(2) . . ? C54 C53 C45 121.6(2) . . ? O4 C54 C55 116.7(2) . . ? O4 C54 C53 122.8(2) . . ? C55 C54 C53 120.5(3) . . ? C54 C55 C56 120.3(3) . . ? C54 C55 H55 119.9 . . ? C56 C55 H55 119.9 . . ? C57 C56 C55 119.9(3) . . ? C57 C56 H56 120.1 . . ? C55 C56 H56 120.1 . . ? C58 C57 C56 118.8(3) . . ? C58 C57 H57 120.6 . . ? C56 C57 H57 120.6 . . ? C57 C58 C53 122.4(3) . . ? C57 C58 H58 118.8 . . ? C53 C58 H58 118.8 . . ? C78 O5 H5 117(2) . . ? C84 O6 H6 109.5 . . ? N62 N61 C75 122.0(2) . . ? N61 N62 C63 119.7(2) . . ? N62 C63 C64 121.0(2) . . ? N62 C63 C77 116.4(2) . . ? C64 C63 C77 122.6(2) . . ? C63 C64 C74 119.7(2) . . ? C63 C64 C65 131.1(2) . . ? C74 C64 C65 108.9(2) . . ? C66 C65 C76 118.9(2) . . ? C66 C65 C64 135.2(2) . . ? C76 C65 C64 105.9(2) . . ? C65 C66 C67 117.9(3) . . ? C65 C66 H66 121.1 . . ? C67 C66 H66 121.1 . . ? C68 C67 C66 122.5(3) . . ? C68 C67 H67 118.8 . . ? C66 C67 H67 118.8 . . ? C67 C68 C69 121.0(3) . . ? C67 C68 H68 119.5 . . ? C69 C68 H68 119.5 . . ? C76 C69 C68 115.9(2) . . ? C76 C69 C70 115.4(2) . . ? C68 C69 C70 128.7(3) . . ? C71 C70 C69 121.4(3) . . ? C71 C70 H70 119.3 . . ? C69 C70 H70 119.3 . . ? C70 C71 C72 121.8(3) . . ? C70 C71 H711 119.1 . . ? C72 C71 H711 119.1 . . ? C73 C72 C71 119.2(3) . . ? C73 C72 H72 120.4 . . ? C71 C72 H72 120.4 . . ? C72 C73 C76 117.5(2) . . ? C72 C73 C74 136.5(3) . . ? C76 C73 C74 105.7(2) . . ? C75 C74 C64 116.6(2) . . ? C75 C74 C73 135.5(2) . . ? C64 C74 C73 107.8(2) . . ? N61 C75 C74 120.8(2) . . ? N61 C75 C83 113.7(2) . . ? C74 C75 C83 125.5(2) . . ? C69 C76 C65 123.6(2) . . ? C69 C76 C73 124.6(2) . . ? C65 C76 C73 111.6(2) . . ? C82 C77 C78 118.8(2) . . ? C82 C77 C63 121.4(2) . . ? C78 C77 C63 119.8(2) . . ? O5 C78 C79 123.0(2) . . ? O5 C78 C77 117.5(2) . . ? C79 C78 C77 119.4(2) . . ? C80 C79 C78 120.5(3) . . ? C80 C79 H79 119.7 . . ? C78 C79 H79 119.7 . . ? C81 C80 C79 119.8(3) . . ? C81 C80 H80 120.1 . . ? C79 C80 H80 120.1 . . ? C82 C81 C80 120.8(3) . . ? C82 C81 H811 119.6 . . ? C80 C81 H811 119.6 . . ? C81 C82 C77 120.7(3) . . ? C81 C82 H82 119.7 . . ? C77 C82 H82 119.7 . . ? C88 C83 C84 117.8(2) . . ? C88 C83 C75 120.2(2) . . ? C84 C83 C75 122.0(2) . . ? O6 C84 C85 116.7(2) . . ? O6 C84 C83 122.9(2) . . ? C85 C84 C83 120.3(3) . . ? C86 C85 C84 120.3(3) . . ? C86 C85 H85 119.9 . . ? C84 C85 H85 119.9 . . ? C87 C86 C85 120.5(3) . . ? C87 C86 H86 119.8 . . ? C85 C86 H86 119.8 . . ? C86 C87 C88 119.2(3) . . ? C86 C87 H87 120.4 . . ? C88 C87 H87 120.4 . . ? C87 C88 C83 121.8(3) . . ? C87 C88 H88 119.1 . . ? C83 C88 H88 119.1 . . ? C108 O7 H7 115(2) . . ? C114 O8 H8 109.5 . . ? N92 N91 C105 122.0(2) . . ? C93 N92 N91 120.6(2) . . ? N92 C93 C94 120.6(2) . . ? N92 C93 C107 115.0(2) . . ? C94 C93 C107 124.3(2) . . ? C93 C94 C104 119.0(2) . . ? C93 C94 C95 131.8(2) . . ? C104 C94 C95 108.8(2) . . ? C96 C95 C106 119.0(3) . . ? C96 C95 C94 135.6(3) . . ? C106 C95 C94 105.3(2) . . ? C95 C96 C97 118.5(3) . . ? C95 C96 H96 120.8 . . ? C97 C96 H96 120.8 . . ? C98 C97 C96 122.3(3) . . ? C98 C97 H97 118.8 . . ? C96 C97 H97 118.8 . . ? C97 C98 C99 120.6(3) . . ? C97 C98 H98 119.7 . . ? C99 C98 H98 119.7 . . ? C106 C99 C98 116.0(3) . . ? C106 C99 C100 115.8(3) . . ? C98 C99 C100 128.1(3) . . ? C101 C100 C99 120.4(3) . . ? C101 C100 H100 119.8 . . ? C99 C100 H100 119.8 . . ? C100 C101 C102 122.8(3) . . ? C100 C101 H101 118.6 . . ? C102 C101 H101 118.6 . . ? C103 C102 C101 118.5(3) . . ? C103 C102 H102 120.8 . . ? C101 C102 H102 120.8 . . ? C102 C103 C106 118.4(3) . . ? C102 C103 C104 136.9(3) . . ? C106 C103 C104 104.7(2) . . ? C94 C104 C105 117.2(2) . . ? C94 C104 C103 108.5(2) . . ? C105 C104 C103 134.2(2) . . ? N91 C105 C104 119.7(2) . . ? N91 C105 C113 114.9(2) . . ? C104 C105 C113 125.3(2) . . ? C99 C106 C95 123.3(3) . . ? C99 C106 C103 124.1(3) . . ? C95 C106 C103 112.6(2) . . ? C108 C107 C112 120.1(3) . . ? C108 C107 C93 120.1(2) . . ? C112 C107 C93 119.7(2) . . ? O7 C108 C107 119.5(2) . . ? O7 C108 C109 120.8(3) . . ? C107 C108 C109 119.7(3) . . ? C110 C109 C108 119.9(3) . . ? C110 C109 H109 120.0 . . ? C108 C109 H109 120.0 . . ? C109 C110 C111 121.6(3) . . ? C109 C110 H110 119.2 . . ? C111 C110 H110 119.2 . . ? C110 C111 C112 117.9(3) . . ? C110 C111 H111 121.0 . . ? C112 C111 H111 121.0 . . ? C107 C112 C111 120.7(3) . . ? C107 C112 H112 119.6 . . ? C111 C112 H112 119.6 . . ? C118 C113 C114 118.3(2) . . ? C118 C113 C105 121.2(2) . . ? C114 C113 C105 120.5(2) . . ? O8 C114 C113 124.2(2) . . ? O8 C114 C115 116.2(2) . . ? C113 C114 C115 119.6(2) . . ? C116 C115 C114 119.6(3) . . ? C116 C115 H115 120.2 . . ? C114 C115 H115 120.2 . . ? C115 C116 C117 121.0(3) . . ? C115 C116 H116 119.5 . . ? C117 C116 H116 119.5 . . ? C118 C117 C116 119.8(3) . . ? C118 C117 H117 120.1 . . ? C116 C117 H117 120.1 . . ? C117 C118 C113 121.6(3) . . ? C117 C118 H118 119.2 . . ? C113 C118 H118 119.2 . . ? Cl2 C119 Cl1 111.3(2) . . ? Cl2 C119 H119 109.4 . . ? Cl1 C119 H119 109.4 . . ? Cl2 C119 H120 109.4 . . ? Cl1 C119 H120 109.4 . . ? H119 C119 H120 108.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N1 N2 C3 -1.7(4) . . . . ? N1 N2 C3 C4 0.4(4) . . . . ? N1 N2 C3 C17 178.9(2) . . . . ? N2 C3 C4 C14 3.2(4) . . . . ? C17 C3 C4 C14 -175.2(2) . . . . ? N2 C3 C4 C5 179.2(2) . . . . ? C17 C3 C4 C5 0.7(4) . . . . ? C3 C4 C5 C6 4.0(5) . . . . ? C14 C4 C5 C6 -179.8(3) . . . . ? C3 C4 C5 C16 -173.8(3) . . . . ? C14 C4 C5 C16 2.5(3) . . . . ? C16 C5 C6 C7 -2.6(4) . . . . ? C4 C5 C6 C7 179.9(3) . . . . ? C5 C6 C7 C8 3.5(4) . . . . ? C6 C7 C8 C9 -0.9(4) . . . . ? C7 C8 C9 C16 -2.4(4) . . . . ? C7 C8 C9 C10 175.8(3) . . . . ? C16 C9 C10 C11 1.5(4) . . . . ? C8 C9 C10 C11 -176.8(3) . . . . ? C9 C10 C11 C12 -2.9(4) . . . . ? C10 C11 C12 C13 0.8(4) . . . . ? C11 C12 C13 C16 2.6(3) . . . . ? C11 C12 C13 C14 176.0(3) . . . . ? C3 C4 C14 C15 -5.3(3) . . . . ? C5 C4 C14 C15 177.9(2) . . . . ? C3 C4 C14 C13 173.0(2) . . . . ? C5 C4 C14 C13 -3.7(3) . . . . ? C12 C13 C14 C15 7.4(5) . . . . ? C16 C13 C14 C15 -178.6(3) . . . . ? C12 C13 C14 C4 -170.5(3) . . . . ? C16 C13 C14 C4 3.5(3) . . . . ? N2 N1 C15 C14 -0.6(4) . . . . ? N2 N1 C15 C23 -178.6(2) . . . . ? C4 C14 C15 N1 4.1(3) . . . . ? C13 C14 C15 N1 -173.6(3) . . . . ? C4 C14 C15 C23 -178.2(2) . . . . ? C13 C14 C15 C23 4.1(5) . . . . ? C8 C9 C16 C5 3.4(4) . . . . ? C10 C9 C16 C5 -175.1(2) . . . . ? C8 C9 C16 C13 -179.4(2) . . . . ? C10 C9 C16 C13 2.1(4) . . . . ? C6 C5 C16 C9 -0.9(4) . . . . ? C4 C5 C16 C9 177.3(2) . . . . ? C6 C5 C16 C13 -178.4(2) . . . . ? C4 C5 C16 C13 -0.2(3) . . . . ? C12 C13 C16 C9 -4.2(4) . . . . ? C14 C13 C16 C9 -179.5(2) . . . . ? C12 C13 C16 C5 173.3(2) . . . . ? C14 C13 C16 C5 -2.0(3) . . . . ? N2 C3 C17 C18 -84.1(3) . . . . ? C4 C3 C17 C18 94.4(3) . . . . ? N2 C3 C17 C22 96.8(3) . . . . ? C4 C3 C17 C22 -84.7(3) . . . . ? C22 C17 C18 O1 177.8(2) . . . . ? C3 C17 C18 O1 -1.4(4) . . . . ? C22 C17 C18 C19 -0.1(4) . . . . ? C3 C17 C18 C19 -179.3(2) . . . . ? O1 C18 C19 C20 -177.0(2) . . . . ? C17 C18 C19 C20 0.9(4) . . . . ? C18 C19 C20 C21 -1.0(4) . . . . ? C19 C20 C21 C22 0.3(5) . . . . ? C20 C21 C22 C17 0.5(5) . . . . ? C18 C17 C22 C21 -0.5(4) . . . . ? C3 C17 C22 C21 178.6(3) . . . . ? N1 C15 C23 C28 -148.3(3) . . . . ? C14 C15 C23 C28 33.9(4) . . . . ? N1 C15 C23 C24 31.4(4) . . . . ? C14 C15 C23 C24 -146.4(3) . . . . ? C28 C23 C24 O2 175.6(3) . . . . ? C15 C23 C24 O2 -4.1(4) . . . . ? C28 C23 C24 C25 -6.9(4) . . . . ? C15 C23 C24 C25 173.5(3) . . . . ? O2 C24 C25 C26 -177.2(3) . . . . ? C23 C24 C25 C26 5.1(5) . . . . ? C24 C25 C26 C27 -0.3(5) . . . . ? C25 C26 C27 C28 -2.6(5) . . . . ? C26 C27 C28 C23 0.7(5) . . . . ? C24 C23 C28 C27 4.0(4) . . . . ? C15 C23 C28 C27 -176.3(3) . . . . ? C45 N31 N32 C33 -4.6(4) . . . . ? N31 N32 C33 C34 3.9(4) . . . . ? N31 N32 C33 C47 178.8(2) . . . . ? N32 C33 C34 C44 2.3(4) . . . . ? C47 C33 C34 C44 -172.1(2) . . . . ? N32 C33 C34 C35 175.4(2) . . . . ? C47 C33 C34 C35 1.0(4) . . . . ? C33 C34 C35 C36 12.5(5) . . . . ? C44 C34 C35 C36 -173.8(3) . . . . ? C33 C34 C35 C46 -169.2(3) . . . . ? C44 C34 C35 C46 4.5(3) . . . . ? C46 C35 C36 C37 2.0(4) . . . . ? C34 C35 C36 C37 -179.8(3) . . . . ? C35 C36 C37 C38 0.5(4) . . . . ? C36 C37 C38 C39 -2.2(4) . . . . ? C37 C38 C39 C46 1.3(4) . . . . ? C37 C38 C39 C40 -176.1(3) . . . . ? C46 C39 C40 C41 0.1(4) . . . . ? C38 C39 C40 C41 177.6(3) . . . . ? C39 C40 C41 C42 0.3(4) . . . . ? C40 C41 C42 C43 -1.8(4) . . . . ? C41 C42 C43 C46 2.9(4) . . . . ? C41 C42 C43 C44 -179.9(3) . . . . ? C33 C34 C44 C45 -7.3(3) . . . . ? C35 C34 C44 C45 178.2(2) . . . . ? C33 C34 C44 C43 170.7(2) . . . . ? C35 C34 C44 C43 -3.8(3) . . . . ? C42 C43 C44 C34 -175.8(3) . . . . ? C46 C43 C44 C34 1.6(3) . . . . ? C42 C43 C44 C45 1.6(5) . . . . ? C46 C43 C44 C45 179.0(3) . . . . ? N32 N31 C45 C44 -0.8(4) . . . . ? N32 N31 C45 C53 178.9(2) . . . . ? C34 C44 C45 N31 6.6(3) . . . . ? C43 C44 C45 N31 -170.6(3) . . . . ? C34 C44 C45 C53 -173.1(2) . . . . ? C43 C44 C45 C53 9.7(4) . . . . ? C40 C39 C46 C35 178.9(2) . . . . ? C38 C39 C46 C35 1.2(4) . . . . ? C40 C39 C46 C43 1.2(4) . . . . ? C38 C39 C46 C43 -176.6(2) . . . . ? C36 C35 C46 C39 -2.9(4) . . . . ? C34 C35 C46 C39 178.4(2) . . . . ? C36 C35 C46 C43 175.1(2) . . . . ? C34 C35 C46 C43 -3.6(3) . . . . ? C42 C43 C46 C39 -2.7(4) . . . . ? C44 C43 C46 C39 179.3(2) . . . . ? C42 C43 C46 C35 179.3(2) . . . . ? C44 C43 C46 C35 1.3(3) . . . . ? N32 C33 C47 C52 -68.9(3) . . . . ? C34 C33 C47 C52 105.8(3) . . . . ? N32 C33 C47 C48 111.0(3) . . . . ? C34 C33 C47 C48 -74.4(3) . . . . ? C52 C47 C48 O3 -177.8(2) . . . . ? C33 C47 C48 O3 2.4(4) . . . . ? C52 C47 C48 C49 2.8(4) . . . . ? C33 C47 C48 C49 -177.0(2) . . . . ? O3 C48 C49 C50 178.8(3) . . . . ? C47 C48 C49 C50 -1.9(4) . . . . ? C48 C49 C50 C51 0.0(4) . . . . ? C49 C50 C51 C52 0.9(4) . . . . ? C48 C47 C52 C51 -2.0(4) . . . . ? C33 C47 C52 C51 177.9(2) . . . . ? C50 C51 C52 C47 0.1(4) . . . . ? N31 C45 C53 C58 -146.9(3) . . . . ? C44 C45 C53 C58 32.8(4) . . . . ? N31 C45 C53 C54 29.9(3) . . . . ? C44 C45 C53 C54 -150.4(3) . . . . ? C58 C53 C54 O4 176.7(3) . . . . ? C45 C53 C54 O4 -0.2(4) . . . . ? C58 C53 C54 C55 -4.3(4) . . . . ? C45 C53 C54 C55 178.9(2) . . . . ? O4 C54 C55 C56 -177.0(3) . . . . ? C53 C54 C55 C56 3.9(4) . . . . ? C54 C55 C56 C57 -1.1(5) . . . . ? C55 C56 C57 C58 -1.3(5) . . . . ? C56 C57 C58 C53 0.8(5) . . . . ? C54 C53 C58 C57 1.9(4) . . . . ? C45 C53 C58 C57 178.8(3) . . . . ? C75 N61 N62 C63 -1.6(3) . . . . ? N61 N62 C63 C64 0.8(4) . . . . ? N61 N62 C63 C77 179.3(2) . . . . ? N62 C63 C64 C74 3.2(4) . . . . ? C77 C63 C64 C74 -175.3(2) . . . . ? N62 C63 C64 C65 175.8(2) . . . . ? C77 C63 C64 C65 -2.7(4) . . . . ? C63 C64 C65 C66 9.4(5) . . . . ? C74 C64 C65 C66 -177.4(3) . . . . ? C63 C64 C65 C76 -171.9(3) . . . . ? C74 C64 C65 C76 1.3(3) . . . . ? C76 C65 C66 C67 1.3(4) . . . . ? C64 C65 C66 C67 179.9(3) . . . . ? C65 C66 C67 C68 1.3(4) . . . . ? C66 C67 C68 C69 -0.5(4) . . . . ? C67 C68 C69 C76 -2.7(4) . . . . ? C67 C68 C69 C70 175.5(3) . . . . ? C76 C69 C70 C71 0.5(4) . . . . ? C68 C69 C70 C71 -177.7(3) . . . . ? C69 C70 C71 C72 -1.7(4) . . . . ? C70 C71 C72 C73 0.4(4) . . . . ? C71 C72 C73 C76 1.9(4) . . . . ? C71 C72 C73 C74 174.1(3) . . . . ? C63 C64 C74 C75 -6.1(3) . . . . ? C65 C64 C74 C75 179.8(2) . . . . ? C63 C64 C74 C73 171.5(2) . . . . ? C65 C64 C74 C73 -2.6(3) . . . . ? C72 C73 C74 C75 7.0(5) . . . . ? C76 C73 C74 C75 179.7(3) . . . . ? C72 C73 C74 C64 -169.9(3) . . . . ? C76 C73 C74 C64 2.9(3) . . . . ? N62 N61 C75 C74 -1.5(4) . . . . ? N62 N61 C75 C83 177.8(2) . . . . ? C64 C74 C75 N61 5.3(3) . . . . ? C73 C74 C75 N61 -171.4(3) . . . . ? C64 C74 C75 C83 -173.9(2) . . . . ? C73 C74 C75 C83 9.4(4) . . . . ? C68 C69 C76 C65 5.4(4) . . . . ? C70 C69 C76 C65 -173.0(2) . . . . ? C68 C69 C76 C73 -179.5(2) . . . . ? C70 C69 C76 C73 2.1(4) . . . . ? C66 C65 C76 C69 -4.8(4) . . . . ? C64 C65 C76 C69 176.2(2) . . . . ? C66 C65 C76 C73 179.5(2) . . . . ? C64 C65 C76 C73 0.5(3) . . . . ? C72 C73 C76 C69 -3.3(4) . . . . ? C74 C73 C76 C69 -177.7(2) . . . . ? C72 C73 C76 C65 172.3(2) . . . . ? C74 C73 C76 C65 -2.1(3) . . . . ? N62 C63 C77 C82 103.3(3) . . . . ? C64 C63 C77 C82 -78.1(3) . . . . ? N62 C63 C77 C78 -76.5(3) . . . . ? C64 C63 C77 C78 102.0(3) . . . . ? C82 C77 C78 O5 177.9(2) . . . . ? C63 C77 C78 O5 -2.2(4) . . . . ? C82 C77 C78 C79 0.7(4) . . . . ? C63 C77 C78 C79 -179.5(2) . . . . ? O5 C78 C79 C80 -176.4(3) . . . . ? C77 C78 C79 C80 0.7(4) . . . . ? C78 C79 C80 C81 -0.2(4) . . . . ? C79 C80 C81 C82 -1.7(4) . . . . ? C80 C81 C82 C77 3.2(5) . . . . ? C78 C77 C82 C81 -2.6(4) . . . . ? C63 C77 C82 C81 177.6(3) . . . . ? N61 C75 C83 C88 -144.5(3) . . . . ? C74 C75 C83 C88 34.7(4) . . . . ? N61 C75 C83 C84 33.4(3) . . . . ? C74 C75 C83 C84 -147.3(3) . . . . ? C88 C83 C84 O6 178.9(3) . . . . ? C75 C83 C84 O6 1.0(4) . . . . ? C88 C83 C84 C85 -3.2(4) . . . . ? C75 C83 C84 C85 178.8(3) . . . . ? O6 C84 C85 C86 179.7(3) . . . . ? C83 C84 C85 C86 1.7(5) . . . . ? C84 C85 C86 C87 0.9(5) . . . . ? C85 C86 C87 C88 -2.0(5) . . . . ? C86 C87 C88 C83 0.5(5) . . . . ? C84 C83 C88 C87 2.1(4) . . . . ? C75 C83 C88 C87 -179.9(3) . . . . ? C105 N91 N92 C93 -2.0(4) . . . . ? N91 N92 C93 C94 5.2(4) . . . . ? N91 N92 C93 C107 -178.3(2) . . . . ? N92 C93 C94 C104 -0.6(4) . . . . ? C107 C93 C94 C104 -176.8(2) . . . . ? N92 C93 C94 C95 171.0(3) . . . . ? C107 C93 C94 C95 -5.1(4) . . . . ? C93 C94 C95 C96 13.3(5) . . . . ? C104 C94 C95 C96 -174.4(3) . . . . ? C93 C94 C95 C106 -168.9(3) . . . . ? C104 C94 C95 C106 3.4(3) . . . . ? C106 C95 C96 C97 3.8(4) . . . . ? C94 C95 C96 C97 -178.6(3) . . . . ? C95 C96 C97 C98 -0.1(4) . . . . ? C96 C97 C98 C99 -3.1(4) . . . . ? C97 C98 C99 C106 2.3(4) . . . . ? C97 C98 C99 C100 -176.8(3) . . . . ? C106 C99 C100 C101 -0.2(4) . . . . ? C98 C99 C100 C101 179.0(3) . . . . ? C99 C100 C101 C102 0.3(4) . . . . ? C100 C101 C102 C103 -0.7(4) . . . . ? C101 C102 C103 C106 1.1(4) . . . . ? C101 C102 C103 C104 177.9(3) . . . . ? C93 C94 C104 C105 -6.7(3) . . . . ? C95 C94 C104 C105 179.8(2) . . . . ? C93 C94 C104 C103 170.6(2) . . . . ? C95 C94 C104 C103 -2.9(3) . . . . ? C102 C103 C104 C94 -175.9(3) . . . . ? C106 C103 C104 C94 1.2(3) . . . . ? C102 C103 C104 C105 0.7(5) . . . . ? C106 C103 C104 C105 177.8(3) . . . . ? N92 N91 C105 C104 -5.8(4) . . . . ? N92 N91 C105 C113 173.0(2) . . . . ? C94 C104 C105 N91 9.9(3) . . . . ? C103 C104 C105 N91 -166.5(3) . . . . ? C94 C104 C105 C113 -168.8(2) . . . . ? C103 C104 C105 C113 14.8(4) . . . . ? C98 C99 C106 C95 1.5(4) . . . . ? C100 C99 C106 C95 -179.3(2) . . . . ? C98 C99 C106 C103 -178.7(2) . . . . ? C100 C99 C106 C103 0.6(4) . . . . ? C96 C95 C106 C99 -4.6(4) . . . . ? C94 C95 C106 C99 177.2(2) . . . . ? C96 C95 C106 C103 175.5(2) . . . . ? C94 C95 C106 C103 -2.7(3) . . . . ? C102 C103 C106 C99 -1.1(4) . . . . ? C104 C103 C106 C99 -178.8(2) . . . . ? C102 C103 C106 C95 178.8(2) . . . . ? C104 C103 C106 C95 1.0(3) . . . . ? N92 C93 C107 C108 114.5(3) . . . . ? C94 C93 C107 C108 -69.1(4) . . . . ? N92 C93 C107 C112 -63.5(3) . . . . ? C94 C93 C107 C112 112.8(3) . . . . ? C112 C107 C108 O7 178.3(3) . . . . ? C93 C107 C108 O7 0.3(4) . . . . ? C112 C107 C108 C109 0.0(4) . . . . ? C93 C107 C108 C109 -178.0(3) . . . . ? O7 C108 C109 C110 -178.1(3) . . . . ? C107 C108 C109 C110 0.2(5) . . . . ? C108 C109 C110 C111 0.2(5) . . . . ? C109 C110 C111 C112 -0.7(5) . . . . ? C108 C107 C112 C111 -0.5(4) . . . . ? C93 C107 C112 C111 177.5(3) . . . . ? C110 C111 C112 C107 0.8(5) . . . . ? N91 C105 C113 C118 -145.0(2) . . . . ? C104 C105 C113 C118 33.7(4) . . . . ? N91 C105 C113 C114 32.4(3) . . . . ? C104 C105 C113 C114 -148.9(3) . . . . ? C118 C113 C114 O8 175.9(2) . . . . ? C105 C113 C114 O8 -1.5(4) . . . . ? C118 C113 C114 C115 -3.8(4) . . . . ? C105 C113 C114 C115 178.7(2) . . . . ? O8 C114 C115 C116 -178.4(3) . . . . ? C113 C114 C115 C116 1.3(4) . . . . ? C114 C115 C116 C117 2.0(5) . . . . ? C115 C116 C117 C118 -2.8(5) . . . . ? C116 C117 C118 C113 0.1(4) . . . . ? C114 C113 C118 C117 3.1(4) . . . . ? C105 C113 C118 C117 -179.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1 H1 N62 0.97(5) 1.85(5) 2.804(3) 166(4) 1_455 yes O2 H2 N1 0.84 1.91 2.639(3) 144.0 . yes O3 H3 N92 0.96(5) 1.78(5) 2.704(3) 162(4) 1_645 yes O4 H4 N31 0.82(5) 1.88(5) 2.637(3) 153(6) . yes O5 H5 N2 0.98(5) 1.85(5) 2.805(3) 167(4) . yes O6 H6 N61 0.84 1.98 2.691(3) 142.4 . yes O7 H7 N32 0.82(4) 1.98(4) 2.771(3) 160(3) 1_565 yes O8 H8 N91 0.84 1.95 2.664(3) 141.9 . yes # End of CIF ============================================================ # Attachment '7,10-bis(3,5-dimethyl-1H-pyrazol-1-yl)-8,9-diazafluo-ranthene.cif' data_SG0635 _database_code_depnum_ccdc_archive 'CCDC 710126' _audit_creation_method SHELXL-97 _audit_creation_date 06-09-25 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C24 H20 N6' _chemical_formula_sum 'C24 H20 N6' _chemical_formula_weight 392.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 96 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 80 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 24 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.4681(2) _cell_length_b 8.0005(1) _cell_length_c 20.8185(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.4706(11) _cell_angle_gamma 90.00 _cell_volume 1904.30(5) _cell_formula_units_Z 4 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 5938 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.0853 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: dichloromethane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.448(1) Frames collected: 424 Seconds exposure per frame: 16 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 31.7 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 52686 _diffrn_reflns_av_R_equivalents 0.0800 _diffrn_reflns_av_sigmaI/netI 0.0550 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 30.03 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 5570 _reflns_number_gt 4012 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+0.3349P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.052(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5570 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1330 _refine_ls_wR_factor_gt 0.1166 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.333 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.068 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.42850(10) 0.17746(13) 0.18860(5) 0.0247(3) Uani 1 1 d . . . N2 N 0.53320(9) 0.10323(13) 0.19080(5) 0.0244(3) Uani 1 1 d . . . N17 N 0.69670(9) -0.00102(13) 0.15042(5) 0.0221(2) Uani 1 1 d . . . N18 N 0.78257(9) 0.01835(15) 0.10892(5) 0.0280(3) Uani 1 1 d . . . N24 N 0.27400(9) 0.32105(13) 0.13936(5) 0.0236(2) Uani 1 1 d . . . N25 N 0.18439(9) 0.29297(14) 0.09295(5) 0.0268(3) Uani 1 1 d . . . C3 C 0.59048(10) 0.08611(15) 0.13804(6) 0.0201(3) Uani 1 1 d . . . C4 C 0.54860(10) 0.15190(14) 0.07781(6) 0.0186(3) Uani 1 1 d . . . C5 C 0.58976(10) 0.16171(15) 0.01205(6) 0.0189(3) Uani 1 1 d . . . C6 C 0.68360(11) 0.10297(16) -0.01931(6) 0.0236(3) Uani 1 1 d . . . H6 H 0.7424 0.0369 0.0031 0.028 Uiso 1 1 calc R . . C7 C 0.69080(11) 0.14254(17) -0.08506(6) 0.0270(3) Uani 1 1 d . . . H7 H 0.7550 0.1006 -0.1064 0.032 Uiso 1 1 calc R . . C8 C 0.60890(12) 0.23904(17) -0.11945(6) 0.0258(3) Uani 1 1 d . . . H8 H 0.6178 0.2642 -0.1634 0.031 Uiso 1 1 calc R . . C9 C 0.51105(11) 0.30097(15) -0.08928(6) 0.0219(3) Uani 1 1 d . . . C10 C 0.42026(11) 0.40370(16) -0.11708(6) 0.0249(3) Uani 1 1 d . . . H10 H 0.4207 0.4370 -0.1609 0.030 Uiso 1 1 calc R . . C11 C 0.33147(11) 0.45555(16) -0.08124(6) 0.0260(3) Uani 1 1 d . . . H11 H 0.2718 0.5252 -0.1009 0.031 Uiso 1 1 calc R . . C12 C 0.32562(11) 0.40891(15) -0.01606(6) 0.0233(3) Uani 1 1 d . . . H12 H 0.2630 0.4459 0.0076 0.028 Uiso 1 1 calc R . . C13 C 0.41263(10) 0.30869(14) 0.01235(6) 0.0190(3) Uani 1 1 d . . . C14 C 0.44069(10) 0.23839(14) 0.07685(6) 0.0191(3) Uani 1 1 d . . . C15 C 0.38378(11) 0.24390(15) 0.13381(6) 0.0210(3) Uani 1 1 d . . . C16 C 0.50464(10) 0.25785(14) -0.02425(6) 0.0190(3) Uani 1 1 d . . . C19 C 0.87043(12) -0.07532(18) 0.13308(7) 0.0302(3) Uani 1 1 d . . . C20 C 0.84312(12) -0.15391(17) 0.19031(7) 0.0300(3) Uani 1 1 d . . . H20 H 0.8922 -0.2266 0.2164 0.036 Uiso 1 1 calc R . . C21 C 0.73198(12) -0.10532(16) 0.20118(6) 0.0255(3) Uani 1 1 d . . . C22 C 0.98055(14) -0.0873(2) 0.09903(9) 0.0469(4) Uani 1 1 d . . . H221 H 0.9617 -0.0770 0.0525 0.070 Uiso 1 1 calc R . . H222 H 1.0180 -0.1956 0.1085 0.070 Uiso 1 1 calc R . . H223 H 1.0340 0.0028 0.1138 0.070 Uiso 1 1 calc R . . C23 C 0.66158(14) -0.15537(19) 0.25519(7) 0.0358(4) Uani 1 1 d . . . H231 H 0.6993 -0.2501 0.2783 0.054 Uiso 1 1 calc R . . H232 H 0.5829 -0.1879 0.2380 0.054 Uiso 1 1 calc R . . H233 H 0.6562 -0.0611 0.2849 0.054 Uiso 1 1 calc R . . C26 C 0.09362(11) 0.37234(18) 0.11468(7) 0.0290(3) Uani 1 1 d . . . C27 C 0.12377(12) 0.44960(18) 0.17437(7) 0.0312(3) Uani 1 1 d . . . H27 H 0.0737 0.5137 0.1991 0.037 Uiso 1 1 calc R . . C28 C 0.23880(12) 0.41444(16) 0.18987(6) 0.0260(3) Uani 1 1 d . . . C29 C -0.02251(13) 0.3706(2) 0.07619(8) 0.0404(4) Uani 1 1 d . . . H291 H -0.0132 0.3232 0.0335 0.061 Uiso 1 1 calc R . . H292 H -0.0524 0.4850 0.0715 0.061 Uiso 1 1 calc R . . H293 H -0.0778 0.3023 0.0984 0.061 Uiso 1 1 calc R . . C30 C 0.31643(13) 0.46123(18) 0.24781(7) 0.0329(3) Uani 1 1 d . . . H301 H 0.3237 0.3663 0.2776 0.049 Uiso 1 1 calc R . . H302 H 0.2827 0.5568 0.2693 0.049 Uiso 1 1 calc R . . H303 H 0.3939 0.4914 0.2347 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0260(6) 0.0273(6) 0.0213(5) 0.0004(4) 0.0040(4) 0.0039(4) N2 0.0262(6) 0.0264(6) 0.0207(5) 0.0005(4) 0.0025(4) 0.0035(4) N17 0.0195(5) 0.0247(5) 0.0216(5) 0.0013(4) -0.0004(4) 0.0013(4) N18 0.0200(6) 0.0363(6) 0.0277(6) 0.0043(5) 0.0029(5) 0.0034(5) N24 0.0214(6) 0.0284(6) 0.0216(5) -0.0002(4) 0.0048(4) 0.0040(4) N25 0.0205(6) 0.0338(6) 0.0264(6) -0.0001(5) 0.0030(4) 0.0020(5) C3 0.0197(6) 0.0191(6) 0.0213(6) -0.0016(5) 0.0001(5) -0.0015(5) C4 0.0179(6) 0.0176(6) 0.0204(6) -0.0019(4) 0.0016(5) -0.0026(4) C5 0.0183(6) 0.0189(6) 0.0196(6) -0.0003(4) 0.0013(5) -0.0026(4) C6 0.0203(6) 0.0269(7) 0.0239(6) -0.0008(5) 0.0034(5) 0.0007(5) C7 0.0224(7) 0.0335(7) 0.0259(7) -0.0017(5) 0.0078(5) 0.0000(5) C8 0.0278(7) 0.0311(7) 0.0192(6) 0.0011(5) 0.0063(5) -0.0047(5) C9 0.0232(6) 0.0219(6) 0.0205(6) 0.0001(5) 0.0013(5) -0.0047(5) C10 0.0266(7) 0.0271(7) 0.0205(6) 0.0025(5) -0.0013(5) -0.0038(5) C11 0.0240(7) 0.0268(7) 0.0263(7) 0.0035(5) -0.0038(5) 0.0008(5) C12 0.0206(6) 0.0242(6) 0.0247(6) -0.0005(5) 0.0005(5) 0.0011(5) C13 0.0189(6) 0.0184(6) 0.0198(6) -0.0010(4) 0.0024(5) -0.0016(5) C14 0.0191(6) 0.0191(6) 0.0191(6) -0.0005(4) 0.0011(5) -0.0014(5) C15 0.0208(6) 0.0216(6) 0.0209(6) -0.0013(5) 0.0025(5) 0.0001(5) C16 0.0198(6) 0.0177(6) 0.0194(6) -0.0010(4) 0.0008(5) -0.0032(5) C19 0.0222(7) 0.0347(8) 0.0333(8) 0.0008(6) -0.0005(6) 0.0045(6) C20 0.0275(7) 0.0311(7) 0.0301(7) 0.0029(6) -0.0056(6) 0.0061(6) C21 0.0278(7) 0.0247(6) 0.0232(6) 0.0011(5) -0.0038(5) 0.0017(5) C22 0.0264(8) 0.0633(11) 0.0514(10) 0.0106(8) 0.0062(7) 0.0148(7) C23 0.0420(9) 0.0366(8) 0.0288(7) 0.0109(6) 0.0033(6) 0.0110(7) C26 0.0223(7) 0.0326(7) 0.0331(7) 0.0046(6) 0.0076(6) 0.0026(5) C27 0.0285(7) 0.0338(7) 0.0329(8) 0.0013(6) 0.0132(6) 0.0067(6) C28 0.0301(7) 0.0255(7) 0.0239(7) 0.0010(5) 0.0113(5) 0.0032(5) C29 0.0242(8) 0.0510(10) 0.0460(9) 0.0040(7) 0.0040(7) 0.0061(7) C30 0.0390(8) 0.0340(8) 0.0263(7) -0.0043(6) 0.0064(6) 0.0059(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C15 1.3250(16) . ? N1 N2 1.3371(15) . ? N2 C3 1.3301(16) . ? N17 N18 1.3686(14) . ? N17 C21 1.3822(16) . ? N17 C3 1.4096(16) . ? N18 C19 1.3231(17) . ? N24 N25 1.3730(15) . ? N24 C28 1.3759(16) . ? N24 C15 1.4150(16) . ? N25 C26 1.3284(17) . ? C3 C4 1.4094(17) . ? C4 C14 1.4166(17) . ? C4 C5 1.4845(16) . ? C5 C6 1.3838(17) . ? C5 C16 1.4146(17) . ? C6 C7 1.4136(18) . ? C6 H6 0.9500 . ? C7 C8 1.3733(19) . ? C7 H7 0.9500 . ? C8 C9 1.4175(18) . ? C8 H8 0.9500 . ? C9 C16 1.4045(17) . ? C9 C10 1.4145(18) . ? C10 C11 1.3726(19) . ? C10 H10 0.9500 . ? C11 C12 1.4140(18) . ? C11 H11 0.9500 . ? C12 C13 1.3771(18) . ? C12 H12 0.9500 . ? C13 C16 1.4088(17) . ? C13 C14 1.4682(16) . ? C14 C15 1.3981(17) . ? C19 C20 1.404(2) . ? C19 C22 1.499(2) . ? C20 C21 1.3682(19) . ? C20 H20 0.9500 . ? C21 C23 1.4891(19) . ? C22 H221 0.9800 . ? C22 H222 0.9800 . ? C22 H223 0.9800 . ? C23 H231 0.9800 . ? C23 H232 0.9800 . ? C23 H233 0.9800 . ? C26 C27 1.407(2) . ? C26 C29 1.500(2) . ? C27 C28 1.3628(19) . ? C27 H27 0.9500 . ? C28 C30 1.4901(19) . ? C29 H291 0.9800 . ? C29 H292 0.9800 . ? C29 H293 0.9800 . ? C30 H301 0.9800 . ? C30 H302 0.9800 . ? C30 H303 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 N1 N2 119.60(10) . . ? C3 N2 N1 121.16(10) . . ? N18 N17 C21 111.65(10) . . ? N18 N17 C3 118.86(10) . . ? C21 N17 C3 129.46(11) . . ? C19 N18 N17 105.07(11) . . ? N25 N24 C28 112.25(10) . . ? N25 N24 C15 119.54(10) . . ? C28 N24 C15 127.97(11) . . ? C26 N25 N24 104.21(11) . . ? N2 C3 C4 122.70(11) . . ? N2 C3 N17 112.05(11) . . ? C4 C3 N17 125.24(11) . . ? C3 C4 C14 115.58(11) . . ? C3 C4 C5 136.83(11) . . ? C14 C4 C5 107.54(10) . . ? C6 C5 C16 117.53(11) . . ? C6 C5 C4 137.06(12) . . ? C16 C5 C4 105.41(10) . . ? C5 C6 C7 119.15(12) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C8 C7 C6 122.79(12) . . ? C8 C7 H7 118.6 . . ? C6 C7 H7 118.6 . . ? C7 C8 C9 119.89(12) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C16 C9 C10 116.42(11) . . ? C16 C9 C8 116.36(11) . . ? C10 C9 C8 127.21(12) . . ? C11 C10 C9 120.45(12) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 122.32(12) . . ? C10 C11 H11 118.8 . . ? C12 C11 H11 118.8 . . ? C13 C12 C11 118.61(12) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C12 C13 C16 118.95(11) . . ? C12 C13 C14 135.70(11) . . ? C16 C13 C14 105.31(10) . . ? C15 C14 C4 117.93(11) . . ? C15 C14 C13 132.85(11) . . ? C4 C14 C13 109.20(10) . . ? N1 C15 C14 122.86(11) . . ? N1 C15 N24 113.07(11) . . ? C14 C15 N24 124.07(11) . . ? C9 C16 C13 123.24(11) . . ? C9 C16 C5 124.25(11) . . ? C13 C16 C5 112.51(11) . . ? N18 C19 C20 111.27(12) . . ? N18 C19 C22 120.08(13) . . ? C20 C19 C22 128.65(13) . . ? C21 C20 C19 106.58(12) . . ? C21 C20 H20 126.7 . . ? C19 C20 H20 126.7 . . ? C20 C21 N17 105.43(11) . . ? C20 C21 C23 127.98(12) . . ? N17 C21 C23 126.58(12) . . ? C19 C22 H221 109.5 . . ? C19 C22 H222 109.5 . . ? H221 C22 H222 109.5 . . ? C19 C22 H223 109.5 . . ? H221 C22 H223 109.5 . . ? H222 C22 H223 109.5 . . ? C21 C23 H231 109.5 . . ? C21 C23 H232 109.5 . . ? H231 C23 H232 109.5 . . ? C21 C23 H233 109.5 . . ? H231 C23 H233 109.5 . . ? H232 C23 H233 109.5 . . ? N25 C26 C27 111.45(12) . . ? N25 C26 C29 120.01(13) . . ? C27 C26 C29 128.53(13) . . ? C28 C27 C26 106.57(12) . . ? C28 C27 H27 126.7 . . ? C26 C27 H27 126.7 . . ? C27 C28 N24 105.51(12) . . ? C27 C28 C30 130.24(12) . . ? N24 C28 C30 124.25(12) . . ? C26 C29 H291 109.5 . . ? C26 C29 H292 109.5 . . ? H291 C29 H292 109.5 . . ? C26 C29 H293 109.5 . . ? H291 C29 H293 109.5 . . ? H292 C29 H293 109.5 . . ? C28 C30 H301 109.5 . . ? C28 C30 H302 109.5 . . ? H301 C30 H302 109.5 . . ? C28 C30 H303 109.5 . . ? H301 C30 H303 109.5 . . ? H302 C30 H303 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N1 N2 C3 -3.97(18) . . . . ? C21 N17 N18 C19 0.91(14) . . . . ? C3 N17 N18 C19 179.26(11) . . . . ? C28 N24 N25 C26 1.02(14) . . . . ? C15 N24 N25 C26 175.78(11) . . . . ? N1 N2 C3 C4 3.50(18) . . . . ? N1 N2 C3 N17 -177.70(10) . . . . ? N18 N17 C3 N2 -158.35(11) . . . . ? C21 N17 C3 N2 19.66(18) . . . . ? N18 N17 C3 C4 20.41(17) . . . . ? C21 N17 C3 C4 -161.58(12) . . . . ? N2 C3 C4 C14 0.05(17) . . . . ? N17 C3 C4 C14 -178.59(11) . . . . ? N2 C3 C4 C5 177.26(13) . . . . ? N17 C3 C4 C5 -1.4(2) . . . . ? C3 C4 C5 C6 4.4(3) . . . . ? C14 C4 C5 C6 -178.19(14) . . . . ? C3 C4 C5 C16 -175.97(13) . . . . ? C14 C4 C5 C16 1.39(12) . . . . ? C16 C5 C6 C7 0.67(18) . . . . ? C4 C5 C6 C7 -179.78(13) . . . . ? C5 C6 C7 C8 0.7(2) . . . . ? C6 C7 C8 C9 -1.1(2) . . . . ? C7 C8 C9 C16 0.01(18) . . . . ? C7 C8 C9 C10 178.83(13) . . . . ? C16 C9 C10 C11 -0.39(18) . . . . ? C8 C9 C10 C11 -179.20(12) . . . . ? C9 C10 C11 C12 -0.5(2) . . . . ? C10 C11 C12 C13 0.37(19) . . . . ? C11 C12 C13 C16 0.64(18) . . . . ? C11 C12 C13 C14 177.80(13) . . . . ? C3 C4 C14 C15 -2.91(16) . . . . ? C5 C4 C14 C15 179.09(10) . . . . ? C3 C4 C14 C13 176.26(10) . . . . ? C5 C4 C14 C13 -1.74(13) . . . . ? C12 C13 C14 C15 3.0(2) . . . . ? C16 C13 C14 C15 -179.60(13) . . . . ? C12 C13 C14 C4 -176.02(13) . . . . ? C16 C13 C14 C4 1.40(13) . . . . ? N2 N1 C15 C14 0.91(18) . . . . ? N2 N1 C15 N24 -178.66(10) . . . . ? C4 C14 C15 N1 2.56(18) . . . . ? C13 C14 C15 N1 -176.38(12) . . . . ? C4 C14 C15 N24 -177.93(11) . . . . ? C13 C14 C15 N24 3.1(2) . . . . ? N25 N24 C15 N1 -134.92(12) . . . . ? C28 N24 C15 N1 38.93(17) . . . . ? N25 N24 C15 C14 45.53(17) . . . . ? C28 N24 C15 C14 -140.63(13) . . . . ? C10 C9 C16 C13 1.45(18) . . . . ? C8 C9 C16 C13 -179.60(11) . . . . ? C10 C9 C16 C5 -177.48(11) . . . . ? C8 C9 C16 C5 1.47(18) . . . . ? C12 C13 C16 C9 -1.60(18) . . . . ? C14 C13 C16 C9 -179.54(11) . . . . ? C12 C13 C16 C5 177.44(11) . . . . ? C14 C13 C16 C5 -0.50(13) . . . . ? C6 C5 C16 C9 -1.82(18) . . . . ? C4 C5 C16 C9 178.50(11) . . . . ? C6 C5 C16 C13 179.15(11) . . . . ? C4 C5 C16 C13 -0.53(13) . . . . ? N17 N18 C19 C20 -0.70(15) . . . . ? N17 N18 C19 C22 178.86(13) . . . . ? N18 C19 C20 C21 0.26(16) . . . . ? C22 C19 C20 C21 -179.25(15) . . . . ? C19 C20 C21 N17 0.30(15) . . . . ? C19 C20 C21 C23 179.19(14) . . . . ? N18 N17 C21 C20 -0.76(14) . . . . ? C3 N17 C21 C20 -178.88(12) . . . . ? N18 N17 C21 C23 -179.67(13) . . . . ? C3 N17 C21 C23 2.2(2) . . . . ? N24 N25 C26 C27 -0.39(15) . . . . ? N24 N25 C26 C29 179.80(12) . . . . ? N25 C26 C27 C28 -0.35(16) . . . . ? C29 C26 C27 C28 179.44(14) . . . . ? C26 C27 C28 N24 0.93(15) . . . . ? C26 C27 C28 C30 -178.90(14) . . . . ? N25 N24 C28 C27 -1.24(14) . . . . ? C15 N24 C28 C27 -175.46(12) . . . . ? N25 N24 C28 C30 178.60(12) . . . . ? C15 N24 C28 C30 4.4(2) . . . . ? # End of CIF ============================================================ # Attachment '7,10-bis(4-chlorobenzyl)-8,9-diazafluoran.cif' data_SG0713 _database_code_depnum_ccdc_archive 'CCDC 710127' _audit_creation_method SHELXL-97 _audit_creation_date 07-03-19 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C28 H18 Cl2 N2' _chemical_formula_sum 'C28 H18 Cl2 N2' _chemical_formula_weight 453.37 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 56 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 36 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; Cl Cl 4 0.1484 0.1585 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 4 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5615(2) _cell_length_b 9.9958(3) _cell_length_c 12.9420(3) _cell_angle_alpha 85.6212(13) _cell_angle_beta 72.6708(12) _cell_angle_gamma 62.3017(14) _cell_volume 1042.65(5) _cell_formula_units_Z 2 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 17967 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description tablet _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.331 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_absorpt_correction_T_min 0.678 _exptl_absorpt_correction_T_max 0.966 _exptl_special_details ; Solvent used: dichloromethane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.502(1) Frames collected: 364 Seconds exposure per frame: 60 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 32.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 26889 _diffrn_reflns_av_R_equivalents 0.0785 _diffrn_reflns_av_sigmaI/netI 0.0497 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 30.01 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.993 _reflns_number_total 6052 _reflns_number_gt 4975 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1125P)^2^+0.7184P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6052 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0742 _refine_ls_wR_factor_ref 0.2015 _refine_ls_wR_factor_gt 0.1924 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.798 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.121 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 1.32992(9) 0.16957(8) -0.12820(5) 0.03851(19) Uani 1 1 d . . . Cl2 Cl 0.57014(7) 0.33457(7) 1.12161(4) 0.02815(16) Uani 1 1 d . . . N1 N 1.1030(2) 0.1802(2) 0.55042(15) 0.0225(4) Uani 1 1 d . . . N2 N 1.0929(2) 0.1182(2) 0.46631(15) 0.0234(4) Uani 1 1 d . . . C3 C 0.9746(3) 0.1976(2) 0.41826(16) 0.0194(4) Uani 1 1 d . . . C4 C 0.8605(2) 0.3490(2) 0.45323(16) 0.0168(4) Uani 1 1 d . . . C5 C 0.7245(2) 0.4654(2) 0.41527(16) 0.0183(4) Uani 1 1 d . . . C6 C 0.6610(3) 0.4744(3) 0.33091(18) 0.0236(4) Uani 1 1 d . . . H6 H 0.7062 0.3899 0.2805 0.028 Uiso 1 1 calc R . . C7 C 0.5254(3) 0.6142(3) 0.32138(19) 0.0279(5) Uani 1 1 d . . . H7 H 0.4811 0.6212 0.2634 0.033 Uiso 1 1 calc R . . C8 C 0.4559(3) 0.7395(3) 0.39261(19) 0.0251(5) Uani 1 1 d . . . H8 H 0.3655 0.8303 0.3831 0.030 Uiso 1 1 calc R . . C9 C 0.5192(2) 0.7331(2) 0.48027(18) 0.0207(4) Uani 1 1 d . . . C10 C 0.4614(3) 0.8497(2) 0.56125(19) 0.0236(4) Uani 1 1 d . . . H10 H 0.3713 0.9459 0.5600 0.028 Uiso 1 1 calc R . . C11 C 0.5364(3) 0.8234(2) 0.64184(19) 0.0249(4) Uani 1 1 d . . . H11 H 0.4953 0.9029 0.6957 0.030 Uiso 1 1 calc R . . C12 C 0.6724(3) 0.6828(2) 0.64797(17) 0.0198(4) Uani 1 1 d . . . H12 H 0.7208 0.6681 0.7049 0.024 Uiso 1 1 calc R . . C13 C 0.7322(2) 0.5683(2) 0.56923(16) 0.0167(4) Uani 1 1 d . . . C14 C 0.8668(2) 0.4117(2) 0.54440(16) 0.0163(4) Uani 1 1 d . . . C15 C 0.9920(2) 0.3225(2) 0.59104(16) 0.0179(4) Uani 1 1 d . . . C16 C 0.6527(2) 0.5948(2) 0.48789(16) 0.0172(4) Uani 1 1 d . . . C17 C 0.9701(3) 0.1116(2) 0.32976(18) 0.0256(5) Uani 1 1 d . . . H171 H 0.8530 0.1472 0.3339 0.031 Uiso 1 1 calc R . . H172 H 1.0169 0.0031 0.3443 0.031 Uiso 1 1 calc R . . C18 C 1.0616(3) 0.1250(2) 0.21564(17) 0.0200(4) Uani 1 1 d . . . C19 C 1.2141(3) 0.1259(3) 0.19172(18) 0.0240(4) Uani 1 1 d . . . H19 H 1.2609 0.1180 0.2486 0.029 Uiso 1 1 calc R . . C20 C 1.2979(3) 0.1380(3) 0.08656(19) 0.0267(5) Uani 1 1 d . . . H20 H 1.4000 0.1407 0.0716 0.032 Uiso 1 1 calc R . . C21 C 1.2306(3) 0.1460(2) 0.00334(18) 0.0246(4) Uani 1 1 d . . . C22 C 1.0840(3) 0.1384(3) 0.02378(19) 0.0276(5) Uani 1 1 d . . . H22 H 1.0411 0.1395 -0.0339 0.033 Uiso 1 1 calc R . . C23 C 1.0007(3) 0.1290(3) 0.12972(19) 0.0263(5) Uani 1 1 d . . . H23 H 0.8993 0.1251 0.1440 0.032 Uiso 1 1 calc R . . C24 C 1.0119(3) 0.3750(2) 0.68949(17) 0.0200(4) Uani 1 1 d . . . H241 H 0.9957 0.4801 0.6815 0.024 Uiso 1 1 calc R . . H242 H 1.1266 0.3105 0.6920 0.024 Uiso 1 1 calc R . . C25 C 0.8933(2) 0.3706(2) 0.79610(16) 0.0173(4) Uani 1 1 d . . . C26 C 0.8627(3) 0.4559(2) 0.88799(18) 0.0221(4) Uani 1 1 d . . . H26 H 0.9120 0.5207 0.8821 0.026 Uiso 1 1 calc R . . C27 C 0.7610(3) 0.4480(3) 0.98830(18) 0.0244(4) Uani 1 1 d . . . H27 H 0.7402 0.5073 1.0503 0.029 Uiso 1 1 calc R . . C28 C 0.6904(3) 0.3523(2) 0.99617(17) 0.0203(4) Uani 1 1 d . . . C29 C 0.7168(3) 0.2673(2) 0.90606(18) 0.0219(4) Uani 1 1 d . . . H29 H 0.6668 0.2030 0.9121 0.026 Uiso 1 1 calc R . . C30 C 0.8176(3) 0.2779(2) 0.80695(17) 0.0210(4) Uani 1 1 d . . . H30 H 0.8356 0.2205 0.7448 0.025 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0453(4) 0.0395(4) 0.0201(3) 0.0040(2) -0.0017(3) -0.0161(3) Cl2 0.0235(3) 0.0424(3) 0.0162(3) 0.0041(2) -0.0040(2) -0.0148(2) N1 0.0179(8) 0.0186(8) 0.0211(9) 0.0045(6) -0.0020(7) -0.0033(7) N2 0.0212(9) 0.0157(8) 0.0219(9) 0.0032(6) -0.0012(7) -0.0028(7) C3 0.0205(9) 0.0157(9) 0.0166(9) 0.0008(7) -0.0004(7) -0.0071(8) C4 0.0160(8) 0.0157(8) 0.0156(9) 0.0027(6) -0.0025(7) -0.0064(7) C5 0.0172(9) 0.0183(9) 0.0180(9) 0.0039(7) -0.0054(7) -0.0074(7) C6 0.0236(10) 0.0263(10) 0.0213(10) 0.0020(8) -0.0077(8) -0.0114(9) C7 0.0256(11) 0.0355(12) 0.0265(11) 0.0102(9) -0.0140(9) -0.0148(10) C8 0.0178(9) 0.0285(11) 0.0281(11) 0.0123(8) -0.0108(8) -0.0091(8) C9 0.0158(9) 0.0183(9) 0.0237(10) 0.0067(7) -0.0052(8) -0.0057(8) C10 0.0177(9) 0.0160(9) 0.0298(11) 0.0046(8) -0.0042(8) -0.0041(8) C11 0.0221(10) 0.0162(9) 0.0281(11) -0.0011(8) -0.0028(9) -0.0047(8) C12 0.0178(9) 0.0191(9) 0.0198(10) 0.0007(7) -0.0037(7) -0.0074(8) C13 0.0154(8) 0.0148(8) 0.0181(9) 0.0044(7) -0.0049(7) -0.0060(7) C14 0.0142(8) 0.0152(8) 0.0156(9) 0.0038(6) -0.0024(7) -0.0052(7) C15 0.0148(8) 0.0186(9) 0.0153(9) 0.0059(7) -0.0020(7) -0.0061(7) C16 0.0146(8) 0.0175(9) 0.0171(9) 0.0043(7) -0.0048(7) -0.0060(7) C17 0.0300(11) 0.0200(10) 0.0243(11) -0.0028(8) 0.0003(9) -0.0140(9) C18 0.0211(9) 0.0136(8) 0.0210(10) -0.0012(7) -0.0043(8) -0.0054(7) C19 0.0252(11) 0.0265(10) 0.0202(10) -0.0019(8) -0.0058(8) -0.0119(9) C20 0.0260(11) 0.0293(11) 0.0256(11) -0.0018(8) -0.0030(9) -0.0156(9) C21 0.0283(11) 0.0204(9) 0.0177(10) 0.0002(7) -0.0036(8) -0.0072(8) C22 0.0281(11) 0.0251(10) 0.0248(11) 0.0003(8) -0.0124(9) -0.0057(9) C23 0.0212(10) 0.0245(10) 0.0293(12) 0.0000(8) -0.0070(9) -0.0076(9) C24 0.0164(9) 0.0240(9) 0.0189(9) 0.0066(7) -0.0066(7) -0.0088(8) C25 0.0143(8) 0.0167(8) 0.0179(9) 0.0042(7) -0.0063(7) -0.0045(7) C26 0.0230(10) 0.0210(9) 0.0242(10) 0.0032(7) -0.0097(8) -0.0105(8) C27 0.0254(10) 0.0260(10) 0.0213(10) -0.0011(8) -0.0089(8) -0.0100(9) C28 0.0184(9) 0.0244(10) 0.0162(9) 0.0045(7) -0.0055(7) -0.0087(8) C29 0.0227(10) 0.0223(10) 0.0217(10) 0.0025(7) -0.0054(8) -0.0122(8) C30 0.0234(10) 0.0202(9) 0.0174(9) -0.0005(7) -0.0047(8) -0.0090(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C21 1.743(2) . ? Cl2 C28 1.739(2) . ? N1 N2 1.342(3) . ? N1 C15 1.343(3) . ? N2 C3 1.344(3) . ? C3 C4 1.400(3) . ? C3 C17 1.505(3) . ? C4 C14 1.407(3) . ? C4 C5 1.474(3) . ? C5 C6 1.378(3) . ? C5 C16 1.416(3) . ? C6 C7 1.426(3) . ? C6 H6 0.9500 . ? C7 C8 1.377(4) . ? C7 H7 0.9500 . ? C8 C9 1.421(3) . ? C8 H8 0.9500 . ? C9 C16 1.401(3) . ? C9 C10 1.417(3) . ? C10 C11 1.378(3) . ? C10 H10 0.9500 . ? C11 C12 1.421(3) . ? C11 H11 0.9500 . ? C12 C13 1.378(3) . ? C12 H12 0.9500 . ? C13 C16 1.416(3) . ? C13 C14 1.471(3) . ? C14 C15 1.396(3) . ? C15 C24 1.509(3) . ? C17 C18 1.508(3) . ? C17 H171 0.9900 . ? C17 H172 0.9900 . ? C18 C23 1.391(3) . ? C18 C19 1.401(3) . ? C19 C20 1.387(3) . ? C19 H19 0.9500 . ? C20 C21 1.390(3) . ? C20 H20 0.9500 . ? C21 C22 1.384(3) . ? C22 C23 1.386(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C25 1.516(3) . ? C24 H241 0.9900 . ? C24 H242 0.9900 . ? C25 C26 1.394(3) . ? C25 C30 1.394(3) . ? C26 C27 1.393(3) . ? C26 H26 0.9500 . ? C27 C28 1.388(3) . ? C27 H27 0.9500 . ? C28 C29 1.387(3) . ? C29 C30 1.387(3) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C15 120.79(18) . . ? N1 N2 C3 121.18(17) . . ? N2 C3 C4 120.68(19) . . ? N2 C3 C17 115.79(18) . . ? C4 C3 C17 123.5(2) . . ? C3 C4 C14 118.01(18) . . ? C3 C4 C5 133.45(19) . . ? C14 C4 C5 108.53(17) . . ? C6 C5 C16 118.61(19) . . ? C6 C5 C4 136.0(2) . . ? C16 C5 C4 105.42(17) . . ? C5 C6 C7 118.1(2) . . ? C5 C6 H6 120.9 . . ? C7 C6 H6 120.9 . . ? C8 C7 C6 122.9(2) . . ? C8 C7 H7 118.6 . . ? C6 C7 H7 118.6 . . ? C7 C8 C9 120.1(2) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C16 C9 C10 116.54(19) . . ? C16 C9 C8 116.1(2) . . ? C10 C9 C8 127.4(2) . . ? C11 C10 C9 119.80(19) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 122.9(2) . . ? C10 C11 H11 118.5 . . ? C12 C11 H11 118.5 . . ? C13 C12 C11 118.3(2) . . ? C13 C12 H12 120.9 . . ? C11 C12 H12 120.9 . . ? C12 C13 C16 118.54(18) . . ? C12 C13 C14 136.01(19) . . ? C16 C13 C14 105.45(17) . . ? C15 C14 C4 118.20(18) . . ? C15 C14 C13 133.14(19) . . ? C4 C14 C13 108.65(17) . . ? N1 C15 C14 120.98(19) . . ? N1 C15 C24 115.34(18) . . ? C14 C15 C24 123.68(18) . . ? C9 C16 C5 124.24(19) . . ? C9 C16 C13 123.84(19) . . ? C5 C16 C13 111.92(17) . . ? C3 C17 C18 115.97(17) . . ? C3 C17 H171 108.3 . . ? C18 C17 H171 108.3 . . ? C3 C17 H172 108.3 . . ? C18 C17 H172 108.3 . . ? H171 C17 H172 107.4 . . ? C23 C18 C19 117.8(2) . . ? C23 C18 C17 120.7(2) . . ? C19 C18 C17 121.4(2) . . ? C20 C19 C18 121.2(2) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C19 C20 C21 119.2(2) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? C22 C21 C20 120.9(2) . . ? C22 C21 Cl1 119.45(18) . . ? C20 C21 Cl1 119.64(18) . . ? C21 C22 C23 119.0(2) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? C22 C23 C18 121.8(2) . . ? C22 C23 H23 119.1 . . ? C18 C23 H23 119.1 . . ? C15 C24 C25 114.17(17) . . ? C15 C24 H241 108.7 . . ? C25 C24 H241 108.7 . . ? C15 C24 H242 108.7 . . ? C25 C24 H242 108.7 . . ? H241 C24 H242 107.6 . . ? C26 C25 C30 118.09(19) . . ? C26 C25 C24 119.99(18) . . ? C30 C25 C24 121.86(18) . . ? C27 C26 C25 121.2(2) . . ? C27 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? C28 C27 C26 118.9(2) . . ? C28 C27 H27 120.5 . . ? C26 C27 H27 120.5 . . ? C29 C28 C27 121.3(2) . . ? C29 C28 Cl2 118.96(16) . . ? C27 C28 Cl2 119.74(17) . . ? C28 C29 C30 118.66(19) . . ? C28 C29 H29 120.7 . . ? C30 C29 H29 120.7 . . ? C29 C30 C25 121.79(19) . . ? C29 C30 H30 119.1 . . ? C25 C30 H30 119.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N1 N2 C3 1.9(3) . . . . ? N1 N2 C3 C4 1.5(3) . . . . ? N1 N2 C3 C17 -176.12(18) . . . . ? N2 C3 C4 C14 -4.2(3) . . . . ? C17 C3 C4 C14 173.22(18) . . . . ? N2 C3 C4 C5 176.9(2) . . . . ? C17 C3 C4 C5 -5.6(3) . . . . ? C3 C4 C5 C6 -3.1(4) . . . . ? C14 C4 C5 C6 178.0(2) . . . . ? C3 C4 C5 C16 178.2(2) . . . . ? C14 C4 C5 C16 -0.7(2) . . . . ? C16 C5 C6 C7 -0.1(3) . . . . ? C4 C5 C6 C7 -178.6(2) . . . . ? C5 C6 C7 C8 -0.1(3) . . . . ? C6 C7 C8 C9 0.1(3) . . . . ? C7 C8 C9 C16 0.1(3) . . . . ? C7 C8 C9 C10 -179.1(2) . . . . ? C16 C9 C10 C11 0.0(3) . . . . ? C8 C9 C10 C11 179.1(2) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? C10 C11 C12 C13 0.4(3) . . . . ? C11 C12 C13 C16 -1.7(3) . . . . ? C11 C12 C13 C14 179.0(2) . . . . ? C3 C4 C14 C15 3.6(3) . . . . ? C5 C4 C14 C15 -177.31(17) . . . . ? C3 C4 C14 C13 -177.49(17) . . . . ? C5 C4 C14 C13 1.6(2) . . . . ? C12 C13 C14 C15 -3.8(4) . . . . ? C16 C13 C14 C15 176.8(2) . . . . ? C12 C13 C14 C4 177.5(2) . . . . ? C16 C13 C14 C4 -1.9(2) . . . . ? N2 N1 C15 C14 -2.5(3) . . . . ? N2 N1 C15 C24 176.64(17) . . . . ? C4 C14 C15 N1 -0.4(3) . . . . ? C13 C14 C15 N1 -178.95(19) . . . . ? C4 C14 C15 C24 -179.39(17) . . . . ? C13 C14 C15 C24 2.0(3) . . . . ? C10 C9 C16 C5 178.95(19) . . . . ? C8 C9 C16 C5 -0.3(3) . . . . ? C10 C9 C16 C13 -1.3(3) . . . . ? C8 C9 C16 C13 179.43(19) . . . . ? C6 C5 C16 C9 0.3(3) . . . . ? C4 C5 C16 C9 179.24(18) . . . . ? C6 C5 C16 C13 -179.45(18) . . . . ? C4 C5 C16 C13 -0.5(2) . . . . ? C12 C13 C16 C9 2.2(3) . . . . ? C14 C13 C16 C9 -178.29(18) . . . . ? C12 C13 C16 C5 -178.01(17) . . . . ? C14 C13 C16 C5 1.5(2) . . . . ? N2 C3 C17 C18 -95.0(2) . . . . ? C4 C3 C17 C18 87.5(3) . . . . ? C3 C17 C18 C23 -144.1(2) . . . . ? C3 C17 C18 C19 39.3(3) . . . . ? C23 C18 C19 C20 3.2(3) . . . . ? C17 C18 C19 C20 179.9(2) . . . . ? C18 C19 C20 C21 -1.4(3) . . . . ? C19 C20 C21 C22 -1.6(3) . . . . ? C19 C20 C21 Cl1 177.22(17) . . . . ? C20 C21 C22 C23 2.8(3) . . . . ? Cl1 C21 C22 C23 -176.09(17) . . . . ? C21 C22 C23 C18 -0.9(3) . . . . ? C19 C18 C23 C22 -2.0(3) . . . . ? C17 C18 C23 C22 -178.8(2) . . . . ? N1 C15 C24 C25 -100.9(2) . . . . ? C14 C15 C24 C25 78.2(2) . . . . ? C15 C24 C25 C26 -160.70(18) . . . . ? C15 C24 C25 C30 22.1(3) . . . . ? C30 C25 C26 C27 0.7(3) . . . . ? C24 C25 C26 C27 -176.63(19) . . . . ? C25 C26 C27 C28 0.5(3) . . . . ? C26 C27 C28 C29 -1.2(3) . . . . ? C26 C27 C28 Cl2 177.30(16) . . . . ? C27 C28 C29 C30 0.8(3) . . . . ? Cl2 C28 C29 C30 -177.76(16) . . . . ? C28 C29 C30 C25 0.4(3) . . . . ? C26 C25 C30 C29 -1.2(3) . . . . ? C24 C25 C30 C29 176.11(19) . . . . ? # End of CIF ============================================================ # Attachment '7,10-bis(methylthio)-8,9-diazafluoranthene.cif' data_SG0703 _database_code_depnum_ccdc_archive 'CCDC 710128' _audit_creation_method SHELXL-97 _audit_creation_date 07-02-05 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C16 H12 N2 S2' _chemical_formula_sum 'C16 H12 N2 S2' _chemical_formula_weight 296.40 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 32 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 24 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 4 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; S S 4 0.1246 0.1234 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/m 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 11 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 5.2259(1) _cell_length_b 18.3970(5) _cell_length_c 7.1402(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.4406(15) _cell_angle_gamma 90.00 _cell_volume 647.33(3) _cell_formula_units_Z 2 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 17869 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.400 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_absorpt_correction_T_min 0.792 _exptl_absorpt_correction_T_max 0.992 _exptl_special_details ; Solvent used: ? Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.510(2) Frames collected: 604 Seconds exposure per frame: 75 Degrees rotation per frame: 1.0 Crystal-Detector distance (mm): 30.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 14381 _diffrn_reflns_av_R_equivalents 0.0799 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 1538 _reflns_number_gt 1273 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.054P)^2^+0.5908P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1538 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.398 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.074 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S10 S 0.15928(10) 0.41882(3) 1.11608(8) 0.01841(18) Uani 1 1 d . . . N1 N 0.0407(3) 0.28663(9) 1.2190(2) 0.0167(4) Uani 1 1 d . . . C2 C 0.1617(4) 0.32319(11) 1.1103(3) 0.0150(4) Uani 1 1 d . . . C3 C 0.2887(4) 0.28793(11) 0.9900(3) 0.0155(4) Uani 1 1 d . . . C4 C 0.4228(4) 0.31393(11) 0.8509(3) 0.0149(4) Uani 1 1 d . . . C5 C 0.4823(4) 0.38010(12) 0.7862(3) 0.0183(4) Uani 1 1 d . . . H5 H 0.4360 0.4241 0.8369 0.022 Uiso 1 1 calc R . . C6 C 0.6148(4) 0.38123(12) 0.6414(3) 0.0208(5) Uani 1 1 d . . . H6 H 0.6547 0.4269 0.5955 0.025 Uiso 1 1 calc R . . C7 C 0.6876(4) 0.31901(12) 0.5654(3) 0.0206(5) Uani 1 1 d . . . H7 H 0.7766 0.3222 0.4693 0.025 Uiso 1 1 calc R . . C8 C 0.6300(6) 0.2500 0.6301(4) 0.0183(6) Uani 1 2 d S . . C9 C 0.4973(6) 0.2500 0.7712(4) 0.0155(6) Uani 1 2 d S . . C11 C -0.0310(4) 0.43647(12) 1.2790(3) 0.0209(5) Uani 1 1 d . . . H111 H -0.2123 0.4151 1.2232 0.031 Uiso 1 1 calc R . . H112 H -0.0473 0.4891 1.2934 0.031 Uiso 1 1 calc R . . H113 H 0.0627 0.4149 1.4094 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S10 0.0246(3) 0.0120(3) 0.0225(3) -0.0003(2) 0.0131(2) -0.0001(2) N1 0.0196(8) 0.0147(9) 0.0181(8) 0.0011(7) 0.0094(7) 0.0003(7) C2 0.0168(9) 0.0132(9) 0.0153(9) 0.0005(8) 0.0057(8) 0.0005(8) C3 0.0153(9) 0.0167(10) 0.0138(9) 0.0008(8) 0.0040(7) -0.0005(8) C4 0.0143(9) 0.0170(10) 0.0132(9) 0.0001(8) 0.0044(7) -0.0007(8) C5 0.0188(10) 0.0171(10) 0.0188(10) 0.0006(8) 0.0060(8) -0.0001(8) C6 0.0216(10) 0.0216(11) 0.0199(10) 0.0048(8) 0.0080(8) -0.0038(8) C7 0.0193(10) 0.0268(12) 0.0177(10) 0.0025(9) 0.0086(8) -0.0027(9) C8 0.0157(13) 0.0251(16) 0.0143(14) 0.000 0.0051(11) 0.000 C9 0.0131(12) 0.0180(14) 0.0146(13) 0.000 0.0038(10) 0.000 C11 0.0245(11) 0.0192(11) 0.0232(11) -0.0033(8) 0.0136(9) 0.0007(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S10 C2 1.760(2) . ? S10 C11 1.794(2) . ? N1 C2 1.335(3) . ? N1 N1 1.348(3) 4_565 ? C2 C3 1.407(3) . ? C3 C3 1.396(4) 4_565 ? C3 C4 1.473(3) . ? C4 C5 1.374(3) . ? C4 C9 1.416(3) . ? C5 C6 1.423(3) . ? C5 H5 0.9500 . ? C6 C7 1.374(3) . ? C6 H6 0.9500 . ? C7 C8 1.417(2) . ? C7 H7 0.9500 . ? C8 C9 1.400(4) . ? C11 H111 0.9800 . ? C11 H112 0.9800 . ? C11 H113 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S10 C11 101.89(10) . . ? C2 N1 N1 120.27(12) . 4_565 ? N1 C2 C3 122.26(19) . . ? N1 C2 S10 118.80(15) . . ? C3 C2 S10 118.93(15) . . ? C3 C3 C2 117.46(12) 4_565 . ? C3 C3 C4 108.94(11) 4_565 . ? C2 C3 C4 133.57(19) . . ? C5 C4 C9 118.52(19) . . ? C5 C4 C3 136.55(19) . . ? C9 C4 C3 104.92(18) . . ? C4 C5 C6 118.5(2) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C7 C6 C5 122.7(2) . . ? C7 C6 H6 118.6 . . ? C5 C6 H6 118.6 . . ? C6 C7 C8 120.0(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 116.39(13) . . ? C7 C8 C7 127.2(3) 4_565 . ? C8 C9 C4 123.86(12) . . ? C4 C9 C4 112.3(2) 4_565 . ? S10 C11 H111 109.5 . . ? S10 C11 H112 109.5 . . ? H111 C11 H112 109.5 . . ? S10 C11 H113 109.5 . . ? H111 C11 H113 109.5 . . ? H112 C11 H113 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 N1 C2 C3 1.1(2) 4_565 . . . ? N1 N1 C2 S10 -179.50(7) 4_565 . . . ? C11 S10 C2 N1 -1.30(18) . . . . ? C11 S10 C2 C3 178.13(16) . . . . ? N1 C2 C3 C3 -1.1(2) . . . 4_565 ? S10 C2 C3 C3 179.53(8) . . . 4_565 ? N1 C2 C3 C4 176.6(2) . . . . ? S10 C2 C3 C4 -2.8(3) . . . . ? C3 C3 C4 C5 179.4(2) 4_565 . . . ? C2 C3 C4 C5 1.6(4) . . . . ? C3 C3 C4 C9 0.34(17) 4_565 . . . ? C2 C3 C4 C9 -177.4(2) . . . . ? C9 C4 C5 C6 0.3(3) . . . . ? C3 C4 C5 C6 -178.7(2) . . . . ? C4 C5 C6 C7 -0.6(3) . . . . ? C5 C6 C7 C8 0.3(3) . . . . ? C6 C7 C8 C9 0.3(3) . . . . ? C6 C7 C8 C7 179.14(19) . . . 4_565 ? C7 C8 C9 C4 179.6(2) . . . 4_565 ? C7 C8 C9 C4 -0.6(4) . . . . ? C5 C4 C9 C8 0.3(4) . . . . ? C3 C4 C9 C8 179.6(2) . . . . ? C5 C4 C9 C4 -179.84(14) . . . 4_565 ? C3 C4 C9 C4 -0.6(3) . . . 4_565 ? # End of CIF ============================================================ # Attachment '7,10-di(pyridin-2-yl)-8,9-diazafluoranthene.cif' data_SG0732 _database_code_depnum_ccdc_archive 'CCDC 710129' _audit_creation_method SHELXL-97 _audit_creation_date 07-09-21 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C24 H14 N4' _chemical_formula_sum 'C24 H14 N4' _chemical_formula_weight 358.40 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 96 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 56 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 16 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n ' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 60 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 21.4230(5) _cell_length_b 10.0153(3) _cell_length_c 7.9227(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1699.88(9) _cell_formula_units_Z 4 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 2843 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.0854 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: dichloromethane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.721(2) Frames collected: 556 Seconds exposure per frame: 108 Degrees rotation per frame: 1.2 Crystal-Detector distance (mm): 32.1 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 39180 _diffrn_reflns_av_R_equivalents 0.1100 _diffrn_reflns_av_sigmaI/netI 0.0580 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 30.01 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 2479 _reflns_number_gt 1785 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0975P)^2^+0.6803P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2479 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1003 _refine_ls_R_factor_gt 0.0698 _refine_ls_wR_factor_ref 0.1879 _refine_ls_wR_factor_gt 0.1673 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.527 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.085 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.02778(7) 0.90226(14) 0.2883(2) 0.0210(4) Uani 1 1 d . . . N11 N 0.16600(7) 0.73297(16) 0.3661(2) 0.0237(4) Uani 1 1 d . . . C2 C 0.05651(8) 0.78726(17) 0.3278(2) 0.0169(4) Uani 1 1 d . . . C3 C 0.02940(7) 0.66351(17) 0.2920(2) 0.0158(4) Uani 1 1 d . . . C4 C 0.04796(8) 0.52381(17) 0.3220(2) 0.0171(4) Uani 1 1 d . . . C5 C 0.09699(8) 0.45993(19) 0.4009(2) 0.0209(4) Uani 1 1 d . . . H5 H 0.1299 0.5096 0.4509 0.025 Uiso 1 1 calc R . . C6 C 0.09702(9) 0.3187(2) 0.4058(3) 0.0237(4) Uani 1 1 d . . . H6 H 0.1303 0.2746 0.4620 0.028 Uiso 1 1 calc R . . C7 C 0.05077(9) 0.24204(18) 0.3325(2) 0.0222(4) Uani 1 1 d . . . H7 H 0.0529 0.1474 0.3371 0.027 Uiso 1 1 calc R . . C8 C 0.0000 0.3061(2) 0.2500 0.0184(5) Uani 1 2 d S . . C9 C 0.0000 0.4450(2) 0.2500 0.0158(5) Uani 1 2 d S . . C10 C 0.11814(8) 0.81141(18) 0.4104(2) 0.0187(4) Uani 1 1 d . . . C12 C 0.22170(9) 0.7612(2) 0.4340(3) 0.0279(5) Uani 1 1 d . . . H12 H 0.2561 0.7061 0.4042 0.033 Uiso 1 1 calc R . . C13 C 0.23232(9) 0.8654(2) 0.5445(3) 0.0272(5) Uani 1 1 d . . . H13 H 0.2729 0.8814 0.5886 0.033 Uiso 1 1 calc R . . C14 C 0.18291(9) 0.9453(2) 0.5893(3) 0.0265(5) Uani 1 1 d . . . H14 H 0.1886 1.0178 0.6651 0.032 Uiso 1 1 calc R . . C15 C 0.12450(8) 0.91822(18) 0.5219(3) 0.0222(4) Uani 1 1 d . . . H15 H 0.0895 0.9715 0.5513 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0176(7) 0.0126(7) 0.0327(10) 0.0002(6) -0.0007(6) 0.0000(6) N11 0.0171(8) 0.0206(8) 0.0333(9) -0.0023(7) 0.0007(7) 0.0019(6) C2 0.0165(8) 0.0137(8) 0.0204(9) -0.0009(7) 0.0036(7) 0.0005(6) C3 0.0137(8) 0.0148(8) 0.0189(9) 0.0001(7) 0.0044(7) 0.0001(6) C4 0.0190(8) 0.0134(8) 0.0188(9) 0.0003(7) 0.0053(7) 0.0000(6) C5 0.0197(8) 0.0181(9) 0.0249(10) 0.0011(7) 0.0013(7) 0.0007(7) C6 0.0217(9) 0.0196(9) 0.0297(10) 0.0043(8) 0.0008(8) 0.0050(7) C7 0.0268(10) 0.0128(8) 0.0270(10) 0.0008(8) 0.0052(8) 0.0029(7) C8 0.0235(12) 0.0119(11) 0.0198(12) 0.000 0.0066(10) 0.000 C9 0.0178(11) 0.0146(12) 0.0149(11) 0.000 0.0043(9) 0.000 C10 0.0179(8) 0.0162(8) 0.0221(9) 0.0024(7) 0.0026(7) -0.0025(7) C12 0.0171(9) 0.0275(10) 0.0391(12) -0.0040(9) 0.0005(8) 0.0020(8) C13 0.0195(9) 0.0313(11) 0.0310(11) 0.0017(9) -0.0034(8) -0.0056(8) C14 0.0295(10) 0.0252(11) 0.0249(10) -0.0046(8) -0.0015(8) -0.0058(8) C15 0.0230(9) 0.0180(9) 0.0257(10) -0.0014(8) 0.0024(8) 0.0009(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N1 1.336(3) 4 ? N1 C2 1.343(2) . ? N11 C10 1.338(2) . ? N11 C12 1.339(2) . ? C2 C3 1.398(2) . ? C2 C10 1.493(2) . ? C3 C3 1.425(3) 4 ? C3 C4 1.474(2) . ? C4 C5 1.380(2) . ? C4 C9 1.416(2) . ? C5 C6 1.415(3) . ? C5 H5 0.9500 . ? C6 C7 1.381(3) . ? C6 H6 0.9500 . ? C7 C8 1.422(2) . ? C7 H7 0.9500 . ? C8 C9 1.391(3) . ? C10 C15 1.394(3) . ? C12 C13 1.381(3) . ? C12 H12 0.9500 . ? C13 C14 1.374(3) . ? C13 H13 0.9500 . ? C14 C15 1.387(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 N1 C2 120.94(10) 4 . ? C10 N11 C12 116.96(17) . . ? N1 C2 C3 121.52(16) . . ? N1 C2 C10 111.62(15) . . ? C3 C2 C10 126.86(16) . . ? C2 C3 C3 117.52(10) . 4 ? C2 C3 C4 134.19(16) . . ? C3 C3 C4 108.28(9) 4 . ? C5 C4 C9 118.46(17) . . ? C5 C4 C3 135.94(16) . . ? C9 C4 C3 105.59(15) . . ? C4 C5 C6 118.43(17) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C7 C6 C5 122.94(18) . . ? C7 C6 H6 118.5 . . ? C5 C6 H6 118.5 . . ? C6 C7 C8 119.42(18) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C9 C8 C7 116.82(12) . . ? C7 C8 C7 126.4(2) . 4 ? C8 C9 C4 123.89(11) . . ? C4 C9 C4 112.2(2) . 4 ? N11 C10 C15 122.80(17) . . ? N11 C10 C2 117.87(16) . . ? C15 C10 C2 119.23(16) . . ? N11 C12 C13 124.12(18) . . ? N11 C12 H12 117.9 . . ? C13 C12 H12 117.9 . . ? C14 C13 C12 118.50(17) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C13 C14 C15 118.79(18) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? C14 C15 C10 118.82(17) . . ? C14 C15 H15 120.6 . . ? C10 C15 H15 120.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 N1 C2 C3 -0.6(3) 4 . . . ? N1 N1 C2 C10 179.3(2) 4 . . . ? N1 C2 C3 C3 1.5(3) . . . 4 ? C10 C2 C3 C3 -178.34(19) . . . 4 ? N1 C2 C3 C4 -178.47(18) . . . . ? C10 C2 C3 C4 1.7(3) . . . . ? C2 C3 C4 C5 3.0(4) . . . . ? C3 C3 C4 C5 -176.9(2) 4 . . . ? C2 C3 C4 C9 -178.46(18) . . . . ? C3 C3 C4 C9 1.6(2) 4 . . . ? C9 C4 C5 C6 0.2(3) . . . . ? C3 C4 C5 C6 178.51(19) . . . . ? C4 C5 C6 C7 1.2(3) . . . . ? C5 C6 C7 C8 -1.0(3) . . . . ? C6 C7 C8 C9 -0.58(19) . . . . ? C6 C7 C8 C7 179.43(19) . . . 4 ? C7 C8 C9 C4 1.97(12) . . . . ? C7 C8 C9 C4 -178.03(12) . . . 4 ? C5 C4 C9 C8 -1.78(19) . . . . ? C3 C4 C9 C8 179.42(8) . . . . ? C5 C4 C9 C4 178.22(19) . . . 4 ? C12 N11 C10 C15 -0.1(3) . . . . ? C12 N11 C10 C2 176.17(17) . . . . ? N1 C2 C10 N11 -139.09(18) . . . . ? C3 C2 C10 N11 40.8(3) . . . . ? N1 C2 C10 C15 37.3(2) . . . . ? C3 C2 C10 C15 -142.86(19) . . . . ? C10 N11 C12 C13 -0.4(3) . . . . ? N11 C12 C13 C14 0.4(3) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? C13 C14 C15 C10 -0.4(3) . . . . ? N11 C10 C15 C14 0.4(3) . . . . ? C2 C10 C15 C14 -175.75(17) . . . . ? # End of CIF ============================================================ # Attachment '7,10-di(thiophen-2-yl)-1,6-dimethyl-8,9-diazafluoran-thene.cif' data_SG0715 _database_code_depnum_ccdc_archive 'CCDC 710130' _audit_creation_method SHELXL-97 _audit_creation_date 07-05-07 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C24 H16 N2 S2' _chemical_formula_sum 'C24 H16 N2 S2' _chemical_formula_weight 396.52 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 96 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 64 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 8 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; S S 8 0.1246 0.1234 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 8.8710(2) _cell_length_b 10.0494(2) _cell_length_c 21.2597(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.1223(15) _cell_angle_gamma 90.00 _cell_volume 1853.00(7) _cell_formula_units_Z 4 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 20788 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description tablet _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_absorpt_correction_T_min 0.843 _exptl_absorpt_correction_T_max 0.969 _exptl_special_details ; Solvent used: dichloromethane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.529(1) Frames collected: 523 Seconds exposure per frame: 20 Degrees rotation per frame: 1.0 Crystal-Detector distance (mm): 32.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 16306 _diffrn_reflns_av_R_equivalents 0.0741 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.45 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.992 _reflns_number_total 2108 _reflns_number_gt 1655 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0765P)^2^+2.6024P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2108 _refine_ls_number_parameters 166 _refine_ls_number_restraints 74 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1484 _refine_ls_wR_factor_gt 0.1367 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.336 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.069 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.5145(2) 0.36115(16) 0.22063(8) 0.0218(4) Uani 1 1 d . . . C2 C 0.5377(2) 0.24620(19) 0.19160(9) 0.0173(4) Uani 1 1 d . A . C3 C 0.5298(2) 0.12280(19) 0.22159(9) 0.0161(4) Uani 1 1 d . . . C4 C 0.5605(2) -0.01597(19) 0.20554(9) 0.0162(4) Uani 1 1 d . . . C5 C 0.6383(2) -0.0789(2) 0.16349(9) 0.0186(4) Uani 1 1 d . . . C6 C 0.6404(2) -0.2210(2) 0.16485(10) 0.0207(5) Uani 1 1 d . . . H6 H 0.6919 -0.2659 0.1361 0.025 Uiso 1 1 calc R . . C7 C 0.5731(2) -0.2966(2) 0.20487(10) 0.0217(5) Uani 1 1 d . . . H7 H 0.5753 -0.3909 0.2024 0.026 Uiso 1 1 calc R . . C8 C 0.5000 -0.2334(3) 0.2500 0.0191(6) Uani 1 2 d S . . C9 C 0.5000 -0.0942(3) 0.2500 0.0161(6) Uani 1 2 d S . . C10 C 0.5549(2) 0.26550(19) 0.12506(10) 0.0215(5) Uani 1 1 d D . . S11 S 0.66770(16) 0.38731(11) 0.10396(6) 0.0350(3) Uani 0.767(3) 1 d PDU A 1 C12 C 0.6068(5) 0.3526(5) 0.02352(17) 0.0386(9) Uani 0.767(3) 1 d PDU A 1 H12 H 0.6428 0.3975 -0.0098 0.046 Uiso 0.767(3) 1 calc PR A 1 C13 C 0.5012(5) 0.2533(4) 0.01339(18) 0.0347(8) Uani 0.767(3) 1 d PDU A 1 H13 H 0.4543 0.2206 -0.0280 0.042 Uiso 0.767(3) 1 calc PR A 1 C14 C 0.4677(12) 0.2028(11) 0.0723(3) 0.0272(12) Uani 0.767(3) 1 d PDU A 1 H14 H 0.3946 0.1347 0.0745 0.033 Uiso 0.767(3) 1 calc PR A 1 S11A S 0.4451(10) 0.1965(10) 0.0590(3) 0.0319(12) Uani 0.233(3) 1 d PDU A 2 C12A C 0.5329(16) 0.2885(14) 0.0087(4) 0.0352(18) Uani 0.233(3) 1 d PDU A 2 H12A H 0.5039 0.2862 -0.0369 0.042 Uiso 0.233(3) 1 calc PR A 2 C13A C 0.6486(16) 0.3646(15) 0.0421(5) 0.0364(16) Uani 0.233(3) 1 d PDU A 2 H13A H 0.7138 0.4186 0.0226 0.044 Uiso 0.233(3) 1 calc PR A 2 C14A C 0.661(2) 0.3544(18) 0.1107(6) 0.038(2) Uani 0.233(3) 1 d PDU A 2 H14A H 0.7336 0.4023 0.1418 0.046 Uiso 0.233(3) 1 calc PR A 2 C15 C 0.7256(3) -0.0100(2) 0.11927(11) 0.0250(5) Uani 1 1 d . . . H151 H 0.6566 0.0055 0.0775 0.037 Uiso 1 1 calc R . . H152 H 0.8121 -0.0660 0.1134 0.037 Uiso 1 1 calc R . . H153 H 0.7650 0.0754 0.1381 0.037 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0349(10) 0.0122(8) 0.0185(9) 0.0008(7) 0.0058(7) -0.0002(7) C2 0.0214(9) 0.0118(9) 0.0180(10) 0.0000(7) 0.0026(8) 0.0002(7) C3 0.0185(9) 0.0129(9) 0.0159(9) 0.0002(7) 0.0016(7) 0.0002(7) C4 0.0189(9) 0.0127(9) 0.0164(9) -0.0005(7) 0.0024(7) 0.0005(7) C5 0.0218(10) 0.0167(10) 0.0166(9) 0.0004(8) 0.0020(8) 0.0029(8) C6 0.0247(10) 0.0165(10) 0.0206(10) -0.0041(8) 0.0043(8) 0.0053(8) C7 0.0268(11) 0.0129(10) 0.0238(11) -0.0039(8) 0.0016(8) 0.0023(8) C8 0.0231(14) 0.0110(13) 0.0215(14) 0.000 0.0010(11) 0.000 C9 0.0200(13) 0.0117(13) 0.0157(13) 0.000 0.0013(11) 0.000 C10 0.0293(11) 0.0148(10) 0.0215(11) 0.0035(8) 0.0078(9) 0.0052(8) S11 0.0499(6) 0.0275(6) 0.0331(5) 0.0076(4) 0.0215(4) -0.0082(4) C12 0.060(2) 0.0376(18) 0.0224(16) 0.0103(16) 0.0189(16) 0.0062(17) C13 0.0520(19) 0.0344(19) 0.0172(14) 0.0039(13) 0.0063(13) 0.0112(14) C14 0.041(3) 0.0277(19) 0.013(3) -0.001(2) 0.007(2) 0.0058(18) S11A 0.040(2) 0.0375(18) 0.016(2) -0.0062(18) 0.0016(18) 0.0074(16) C12A 0.053(3) 0.035(3) 0.019(3) 0.008(3) 0.013(3) 0.006(3) C13A 0.053(3) 0.035(3) 0.025(3) 0.009(3) 0.018(3) 0.000(3) C14A 0.054(4) 0.034(4) 0.030(4) 0.012(3) 0.017(3) -0.004(3) C15 0.0301(11) 0.0217(11) 0.0263(11) 0.0031(9) 0.0134(9) 0.0068(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N1 1.327(3) 2_655 ? N1 C2 1.346(3) . ? C2 C3 1.403(3) . ? C2 C10 1.467(3) . ? C3 C3 1.417(4) 2_655 ? C3 C4 1.475(3) . ? C4 C5 1.391(3) . ? C4 C9 1.419(2) . ? C5 C6 1.428(3) . ? C5 C15 1.507(3) . ? C6 C7 1.368(3) . ? C6 H6 0.9500 . ? C7 C8 1.416(2) . ? C7 H7 0.9500 . ? C8 C9 1.399(4) . ? C10 C14 1.374(7) . ? C10 C14A 1.381(8) . ? C10 S11A 1.682(4) . ? C10 S11 1.700(2) . ? S11 C12 1.717(4) . ? C12 C13 1.355(6) . ? C12 H12 0.9500 . ? C13 C14 1.439(9) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? S11A C12A 1.718(6) . ? C12A C13A 1.356(7) . ? C12A H12A 0.9500 . ? C13A C14A 1.441(10) . ? C13A H13A 0.9500 . ? C14A H14A 0.9500 . ? C15 H151 0.9800 . ? C15 H152 0.9800 . ? C15 H153 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 N1 C2 120.67(11) 2_655 . ? N1 C2 C3 121.57(18) . . ? N1 C2 C10 112.68(17) . . ? C3 C2 C10 125.46(18) . . ? C2 C3 C3 116.77(12) . 2_655 ? C2 C3 C4 134.57(18) . . ? C3 C3 C4 108.50(11) 2_655 . ? C5 C4 C9 118.96(18) . . ? C5 C4 C3 136.02(18) . . ? C9 C4 C3 104.83(17) . . ? C4 C5 C6 116.62(18) . . ? C4 C5 C15 125.54(18) . . ? C6 C5 C15 117.78(18) . . ? C7 C6 C5 124.21(19) . . ? C7 C6 H6 117.9 . . ? C5 C6 H6 117.9 . . ? C6 C7 C8 119.6(2) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C9 C8 C7 116.66(13) . . ? C7 C8 C7 126.7(3) 2_655 . ? C8 C9 C4 123.65(12) . . ? C4 C9 C4 112.7(2) 2_655 . ? C14 C10 C2 124.8(4) . . ? C14A C10 C2 120.9(6) . . ? C14A C10 S11A 112.6(4) . . ? C2 C10 S11A 126.3(3) . . ? C14 C10 S11 112.1(4) . . ? C2 C10 S11 122.40(15) . . ? C10 S11 C12 92.11(17) . . ? C13 C12 S11 111.7(3) . . ? C13 C12 H12 124.1 . . ? S11 C12 H12 124.1 . . ? C12 C13 C14 112.6(4) . . ? C12 C13 H13 123.7 . . ? C14 C13 H13 123.7 . . ? C10 C14 C13 111.4(6) . . ? C10 C14 H14 124.3 . . ? C13 C14 H14 124.3 . . ? C10 S11A C12A 92.2(3) . . ? C13A C12A S11A 111.7(5) . . ? C13A C12A H12A 124.1 . . ? S11A C12A H12A 124.1 . . ? C12A C13A C14A 112.3(6) . . ? C12A C13A H13A 123.8 . . ? C14A C13A H13A 123.8 . . ? C10 C14A C13A 111.0(7) . . ? C10 C14A H14A 124.5 . . ? C13A C14A H14A 124.5 . . ? C5 C15 H151 109.5 . . ? C5 C15 H152 109.5 . . ? H151 C15 H152 109.5 . . ? C5 C15 H153 109.5 . . ? H151 C15 H153 109.5 . . ? H152 C15 H153 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 N1 C2 C3 0.9(4) 2_655 . . . ? N1 N1 C2 C10 175.1(2) 2_655 . . . ? N1 C2 C3 C3 10.8(3) . . . 2_655 ? C10 C2 C3 C3 -162.6(2) . . . 2_655 ? N1 C2 C3 C4 -174.3(2) . . . . ? C10 C2 C3 C4 12.3(4) . . . . ? C2 C3 C4 C5 16.8(4) . . . . ? C3 C3 C4 C5 -168.0(2) 2_655 . . . ? C2 C3 C4 C9 -168.5(2) . . . . ? C3 C3 C4 C9 6.7(2) 2_655 . . . ? C9 C4 C5 C6 5.0(3) . . . . ? C3 C4 C5 C6 179.1(2) . . . . ? C9 C4 C5 C15 -172.08(17) . . . . ? C3 C4 C5 C15 2.0(4) . . . . ? C4 C5 C6 C7 -0.7(3) . . . . ? C15 C5 C6 C7 176.6(2) . . . . ? C5 C6 C7 C8 -2.3(3) . . . . ? C6 C7 C8 C9 0.8(2) . . . . ? C6 C7 C8 C7 -179.2(2) . . . 2_655 ? C7 C8 C9 C4 3.66(13) 2_655 . . 2_655 ? C7 C8 C9 C4 -176.34(13) . . . 2_655 ? C7 C8 C9 C4 -176.34(13) 2_655 . . . ? C7 C8 C9 C4 3.66(13) . . . . ? C5 C4 C9 C8 -6.7(2) . . . . ? C3 C4 C9 C8 177.53(9) . . . . ? C5 C4 C9 C4 173.3(2) . . . 2_655 ? C3 C4 C9 C4 -2.47(9) . . . 2_655 ? N1 C2 C10 C14 -125.0(7) . . . . ? C3 C2 C10 C14 48.9(7) . . . . ? N1 C2 C10 C14A 53.2(12) . . . . ? C3 C2 C10 C14A -132.9(12) . . . . ? N1 C2 C10 S11A -121.8(5) . . . . ? C3 C2 C10 S11A 52.1(6) . . . . ? N1 C2 C10 S11 45.2(2) . . . . ? C3 C2 C10 S11 -140.91(19) . . . . ? C14 C10 S11 C12 -2.4(6) . . . . ? C2 C10 S11 C12 -173.7(2) . . . . ? C10 S11 C12 C13 1.4(4) . . . . ? S11 C12 C13 C14 -0.1(8) . . . . ? C2 C10 C14 C13 173.8(5) . . . . ? S11 C10 C14 C13 2.7(10) . . . . ? C12 C13 C14 C10 -1.7(11) . . . . ? C14A C10 S11A C12A -2.0(14) . . . . ? C2 C10 S11A C12A 173.3(6) . . . . ? C10 S11A C12A C13A 3.1(15) . . . . ? S11A C12A C13A C14A -3(2) . . . . ? C2 C10 C14A C13A -175.2(11) . . . . ? S11A C10 C14A C13A 0(2) . . . . ? C12A C13A C14A C10 2(2) . . . . ? # End of CIF ============================================================ # Attachment '7,10-di(thiophen-2-yl)-8,9-diazafluoranthene.cif' data_SG0705 _database_code_depnum_ccdc_archive 'CCDC 710131' _audit_creation_method SHELXL-97 _audit_creation_date 07-02-07 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C22 H12 N2 S2' _chemical_formula_sum 'C22 H12 N2 S2' _chemical_formula_weight 368.47 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 88 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 48 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 8 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; S S 8 0.1246 0.1234 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n ' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 60 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 21.4777(6) _cell_length_b 10.0334(3) _cell_length_c 7.5250(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1621.60(9) _cell_formula_units_Z 4 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 25449 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.336 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_absorpt_correction_T_min 0.814 _exptl_absorpt_correction_T_max 0.998 _exptl_special_details ; Solvent used: ? Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.825(2) Frames collected: 262 Seconds exposure per frame: 162 Degrees rotation per frame: 1.8 Crystal-Detector distance (mm): 32.2 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 24334 _diffrn_reflns_av_R_equivalents 0.0857 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 30.03 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_total 2364 _reflns_number_gt 1861 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0765P)^2^+0.9575P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2364 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0700 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1365 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.424 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.078 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S11 S 0.84804(2) -0.25885(5) 0.04227(7) 0.02602(17) Uani 1 1 d . . . N1 N 0.97041(7) -0.21648(14) 0.2245(2) 0.0189(3) Uani 1 1 d . . . C2 C 0.94020(8) -0.10111(16) 0.1923(2) 0.0168(3) Uani 1 1 d . . . C3 C 0.96975(7) 0.02247(16) 0.2128(2) 0.0155(3) Uani 1 1 d . . . C4 C 0.95161(8) 0.16160(16) 0.1780(2) 0.0168(3) Uani 1 1 d . . . C5 C 0.90392(8) 0.22576(18) 0.0898(2) 0.0197(4) Uani 1 1 d . . . H5 H 0.8712 0.1762 0.0363 0.024 Uiso 1 1 calc R . . C6 C 0.90454(9) 0.36694(18) 0.0803(3) 0.0230(4) Uani 1 1 d . . . H6 H 0.8724 0.4108 0.0161 0.028 Uiso 1 1 calc R . . C7 C 0.95001(9) 0.44289(18) 0.1609(3) 0.0235(4) Uani 1 1 d . . . H7 H 0.9478 0.5374 0.1567 0.028 Uiso 1 1 calc R . . C8 C 1.0000 0.3798(2) 0.2500 0.0195(5) Uani 1 2 d S . . C9 C 1.0000 0.2404(2) 0.2500 0.0175(5) Uani 1 2 d S . . C10 C 0.87392(8) -0.11732(17) 0.1495(2) 0.0185(3) Uani 1 1 d . . . C12 C 0.77220(9) -0.2098(2) 0.0596(3) 0.0300(5) Uani 1 1 d . . . H12 H 0.7381 -0.2594 0.0139 0.036 Uiso 1 1 calc R . . C13 C 0.76613(9) -0.0914(2) 0.1465(3) 0.0281(4) Uani 1 1 d . . . H13 H 0.7273 -0.0497 0.1693 0.034 Uiso 1 1 calc R . . C14 C 0.82439(8) -0.03739(18) 0.1992(3) 0.0215(4) Uani 1 1 d . . . H14 H 0.8289 0.0444 0.2616 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S11 0.0257(3) 0.0193(2) 0.0331(3) -0.00390(18) -0.00191(19) -0.00525(16) N1 0.0193(7) 0.0151(7) 0.0224(8) -0.0003(6) 0.0020(6) -0.0004(5) C2 0.0192(8) 0.0149(7) 0.0164(8) 0.0003(6) 0.0013(6) -0.0004(6) C3 0.0171(7) 0.0136(7) 0.0159(8) -0.0002(6) 0.0022(6) 0.0000(6) C4 0.0191(8) 0.0142(7) 0.0172(8) 0.0000(6) 0.0035(6) -0.0003(6) C5 0.0188(8) 0.0207(8) 0.0196(8) 0.0015(7) 0.0023(6) 0.0011(6) C6 0.0224(8) 0.0198(8) 0.0268(9) 0.0050(7) 0.0044(7) 0.0058(6) C7 0.0264(9) 0.0150(8) 0.0291(10) 0.0029(7) 0.0064(7) 0.0031(6) C8 0.0221(11) 0.0149(10) 0.0213(12) 0.000 0.0059(9) 0.000 C9 0.0203(11) 0.0148(10) 0.0174(11) 0.000 0.0036(9) 0.000 C10 0.0216(8) 0.0159(7) 0.0178(8) -0.0004(6) -0.0006(6) -0.0034(6) C12 0.0235(9) 0.0312(10) 0.0354(11) 0.0029(9) -0.0046(8) -0.0093(8) C13 0.0193(9) 0.0322(10) 0.0327(11) 0.0027(8) 0.0004(7) -0.0015(7) C14 0.0197(8) 0.0204(8) 0.0244(9) -0.0001(7) 0.0003(7) -0.0010(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S11 C12 1.707(2) . ? S11 C10 1.7252(18) . ? N1 N1 1.328(3) 4_755 ? N1 C2 1.349(2) . ? C2 C3 1.401(2) . ? C2 C10 1.469(2) . ? C3 C3 1.415(3) 4_755 ? C3 C4 1.473(2) . ? C4 C5 1.380(2) . ? C4 C9 1.414(2) . ? C5 C6 1.418(2) . ? C5 H5 0.9500 . ? C6 C7 1.379(3) . ? C6 H6 0.9500 . ? C7 C8 1.415(2) . ? C7 H7 0.9500 . ? C8 C9 1.399(3) . ? C10 C14 1.384(2) . ? C12 C13 1.362(3) . ? C12 H12 0.9500 . ? C13 C14 1.420(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 S11 C10 91.96(10) . . ? N1 N1 C2 120.83(9) 4_755 . ? N1 C2 C3 121.43(15) . . ? N1 C2 C10 114.25(15) . . ? C3 C2 C10 124.13(15) . . ? C2 C3 C3 117.36(10) . 4_755 ? C2 C3 C4 134.37(15) . . ? C3 C3 C4 108.25(9) 4_755 . ? C5 C4 C9 117.99(16) . . ? C5 C4 C3 136.39(16) . . ? C9 C4 C3 105.51(15) . . ? C4 C5 C6 118.89(17) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C7 C6 C5 122.43(17) . . ? C7 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? C6 C7 C8 119.88(17) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C9 C8 C7 116.59(12) . . ? C7 C8 C7 126.8(2) . 4_755 ? C8 C9 C4 123.99(10) . . ? C4 C9 C4 112.0(2) . 4_755 ? C14 C10 C2 128.44(16) . . ? C14 C10 S11 110.85(13) . . ? C2 C10 S11 120.40(13) . . ? C13 C12 S11 112.32(15) . . ? C13 C12 H12 123.8 . . ? S11 C12 H12 123.8 . . ? C12 C13 C14 112.49(17) . . ? C12 C13 H13 123.8 . . ? C14 C13 H13 123.8 . . ? C10 C14 C13 112.37(17) . . ? C10 C14 H14 123.8 . . ? C13 C14 H14 123.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 N1 C2 C3 -0.6(3) 4_755 . . . ? N1 N1 C2 C10 -175.89(19) 4_755 . . . ? N1 C2 C3 C3 -6.8(3) . . . 4_755 ? C10 C2 C3 C3 168.03(18) . . . 4_755 ? N1 C2 C3 C4 175.24(18) . . . . ? C10 C2 C3 C4 -10.0(3) . . . . ? C2 C3 C4 C5 -11.8(4) . . . . ? C3 C3 C4 C5 170.1(2) 4_755 . . . ? C2 C3 C4 C9 172.45(17) . . . . ? C3 C3 C4 C9 -5.7(2) 4_755 . . . ? C9 C4 C5 C6 -2.0(2) . . . . ? C3 C4 C5 C6 -177.36(18) . . . . ? C4 C5 C6 C7 -2.1(3) . . . . ? C5 C6 C7 C8 3.1(3) . . . . ? C6 C7 C8 C9 0.13(19) . . . . ? C6 C7 C8 C7 -179.87(19) . . . 4_755 ? C7 C8 C9 C4 -4.43(12) . . . . ? C7 C8 C9 C4 175.56(12) . . . 4_755 ? C7 C8 C9 C4 -4.43(12) 4_755 . . 4_755 ? C5 C4 C9 C8 5.40(18) . . . . ? C3 C4 C9 C8 -177.89(8) . . . . ? C5 C4 C9 C4 -174.60(18) . . . 4_755 ? C3 C4 C9 C4 2.11(8) . . . 4_755 ? N1 C2 C10 C14 142.03(19) . . . . ? C3 C2 C10 C14 -33.1(3) . . . . ? N1 C2 C10 S11 -30.9(2) . . . . ? C3 C2 C10 S11 154.01(14) . . . . ? C12 S11 C10 C14 1.23(15) . . . . ? C12 S11 C10 C2 175.29(15) . . . . ? C10 S11 C12 C13 -1.13(18) . . . . ? S11 C12 C13 C14 0.7(2) . . . . ? C2 C10 C14 C13 -174.50(18) . . . . ? S11 C10 C14 C13 -1.0(2) . . . . ? C12 C13 C14 C10 0.2(3) . . . . ? # End of CIF ============================================================ # Attachment '7,10-dimethyl-8,9-diazafluoran.cif' data_SG0643 _database_code_depnum_ccdc_archive 'CCDC 710132' _audit_creation_method SHELXL-97 _audit_creation_date 06-11-22 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C16 H12 N2' _chemical_formula_sum 'C16 H12 N2' _chemical_formula_weight 232.28 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 128 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 96 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 16 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.6806(12) _cell_length_b 10.8157(9) _cell_length_c 15.0851(13) _cell_angle_alpha 90.00 _cell_angle_beta 118.174(4) _cell_angle_gamma 90.00 _cell_volume 2255.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 2104 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.0818 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: deuterochloroform Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.812(4) Frames collected: 211 Seconds exposure per frame: 40 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 16289 _diffrn_reflns_av_R_equivalents 0.1420 _diffrn_reflns_av_sigmaI/netI 0.0811 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.06 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 1999 _reflns_number_gt 1251 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0848P)^2^+1.5517P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1999 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1785 _refine_ls_wR_factor_gt 0.1491 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.274 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.060 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.32086(18) 0.2810(2) 0.71965(18) 0.0330(7) Uani 1 1 d . . . N2 N 0.3913(2) 0.2017(2) 0.7781(2) 0.0374(7) Uani 1 1 d . . . C3 C 0.4765(2) 0.2429(3) 0.8509(2) 0.0292(8) Uani 1 1 d . . . C4 C 0.4945(2) 0.3693(3) 0.8685(2) 0.0231(7) Uani 1 1 d . . . C5 C 0.57769(19) 0.4413(3) 0.94143(19) 0.0213(7) Uani 1 1 d . . . C6 C 0.6659(2) 0.4154(3) 1.0228(2) 0.0280(8) Uani 1 1 d . . . H6 H 0.6859 0.3324 1.0421 0.034 Uiso 1 1 calc R . . C7 C 0.7261(2) 0.5153(3) 1.0770(2) 0.0333(8) Uani 1 1 d . . . H7 H 0.7874 0.4979 1.1327 0.040 Uiso 1 1 calc R . . C8 C 0.6995(2) 0.6358(3) 1.0523(2) 0.0314(8) Uani 1 1 d . . . H8 H 0.7425 0.7000 1.0907 0.038 Uiso 1 1 calc R . . C9 C 0.6091(2) 0.6663(3) 0.9705(2) 0.0247(7) Uani 1 1 d . . . C10 C 0.5696(2) 0.7862(3) 0.9362(2) 0.0342(8) Uani 1 1 d . . . H10 H 0.6064 0.8578 0.9680 0.041 Uiso 1 1 calc R . . C11 C 0.4779(2) 0.7977(3) 0.8571(2) 0.0362(9) Uani 1 1 d . . . H11 H 0.4528 0.8784 0.8354 0.043 Uiso 1 1 calc R . . C12 C 0.4191(2) 0.6958(3) 0.8066(2) 0.0271(8) Uani 1 1 d . . . H12 H 0.3553 0.7075 0.7535 0.033 Uiso 1 1 calc R . . C13 C 0.45629(19) 0.5783(3) 0.83611(19) 0.0198(7) Uani 1 1 d . . . C14 C 0.42195(19) 0.4516(3) 0.8061(2) 0.0208(7) Uani 1 1 d . . . C15 C 0.33495(19) 0.4037(3) 0.7321(2) 0.0256(7) Uani 1 1 d . . . C16 C 0.55101(19) 0.5668(3) 0.91767(19) 0.0209(7) Uani 1 1 d . . . C17 C 0.5498(3) 0.1459(3) 0.9101(3) 0.0454(10) Uani 1 1 d . . . H171 H 0.5575 0.1424 0.9784 0.068 Uiso 1 1 calc R . . H172 H 0.6120 0.1666 0.9133 0.068 Uiso 1 1 calc R . . H173 H 0.5278 0.0654 0.8775 0.068 Uiso 1 1 calc R . . C18 C 0.2523(2) 0.4839(3) 0.6627(2) 0.0348(8) Uani 1 1 d . . . H181 H 0.1975 0.4318 0.6185 0.052 Uiso 1 1 calc R . . H182 H 0.2725 0.5345 0.6220 0.052 Uiso 1 1 calc R . . H183 H 0.2330 0.5379 0.7023 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0324(15) 0.0352(17) 0.0304(15) -0.0071(13) 0.0140(12) -0.0097(13) N2 0.0381(17) 0.0354(17) 0.0413(17) -0.0068(14) 0.0210(14) -0.0112(14) C3 0.0336(18) 0.0255(18) 0.0303(18) 0.0037(14) 0.0167(15) -0.0029(14) C4 0.0242(16) 0.0262(17) 0.0242(16) 0.0017(13) 0.0159(14) 0.0004(13) C5 0.0190(15) 0.0291(17) 0.0154(15) -0.0018(13) 0.0079(12) -0.0031(13) C6 0.0247(16) 0.0378(19) 0.0224(16) 0.0040(15) 0.0117(14) 0.0024(14) C7 0.0202(16) 0.057(2) 0.0199(16) -0.0024(16) 0.0070(13) -0.0014(16) C8 0.0225(17) 0.045(2) 0.0276(18) -0.0148(16) 0.0127(15) -0.0114(15) C9 0.0202(16) 0.0336(18) 0.0219(16) -0.0084(14) 0.0113(13) -0.0064(14) C10 0.0357(19) 0.0270(18) 0.043(2) -0.0115(16) 0.0211(17) -0.0061(15) C11 0.036(2) 0.0272(19) 0.049(2) 0.0026(16) 0.0237(17) 0.0064(15) C12 0.0223(16) 0.0285(19) 0.0280(17) 0.0004(14) 0.0097(14) 0.0019(14) C13 0.0166(14) 0.0271(17) 0.0175(15) -0.0016(13) 0.0096(12) -0.0029(13) C14 0.0192(15) 0.0275(17) 0.0182(15) 0.0007(13) 0.0109(13) -0.0003(13) C15 0.0196(16) 0.037(2) 0.0194(15) -0.0065(14) 0.0086(13) -0.0067(14) C16 0.0195(15) 0.0277(18) 0.0172(15) -0.0004(13) 0.0100(13) -0.0001(13) C17 0.053(2) 0.026(2) 0.054(2) 0.0099(17) 0.023(2) 0.0010(17) C18 0.0202(16) 0.053(2) 0.0256(17) -0.0070(16) 0.0063(14) -0.0052(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C15 1.344(4) . ? N1 N2 1.347(4) . ? N2 C3 1.343(4) . ? C3 C4 1.396(4) . ? C3 C17 1.500(4) . ? C4 C14 1.400(4) . ? C4 C5 1.470(4) . ? C5 C6 1.377(4) . ? C5 C16 1.416(4) . ? C6 C7 1.413(4) . ? C6 H6 0.9500 . ? C7 C8 1.365(4) . ? C7 H7 0.9500 . ? C8 C9 1.411(4) . ? C8 H8 0.9500 . ? C9 C16 1.392(4) . ? C9 C10 1.425(4) . ? C10 C11 1.374(4) . ? C10 H10 0.9500 . ? C11 C12 1.407(4) . ? C11 H11 0.9500 . ? C12 C13 1.381(4) . ? C12 H12 0.9500 . ? C13 C16 1.418(4) . ? C13 C14 1.464(4) . ? C14 C15 1.392(4) . ? C15 C18 1.499(4) . ? C17 H171 0.9800 . ? C17 H172 0.9800 . ? C17 H173 0.9800 . ? C18 H181 0.9800 . ? C18 H182 0.9800 . ? C18 H183 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 N1 N2 120.5(2) . . ? C3 N2 N1 121.0(3) . . ? N2 C3 C4 121.0(3) . . ? N2 C3 C17 116.2(3) . . ? C4 C3 C17 122.8(3) . . ? C3 C4 C14 117.8(3) . . ? C3 C4 C5 133.6(3) . . ? C14 C4 C5 108.6(2) . . ? C6 C5 C16 118.2(3) . . ? C6 C5 C4 136.3(3) . . ? C16 C5 C4 105.5(2) . . ? C5 C6 C7 118.4(3) . . ? C5 C6 H6 120.8 . . ? C7 C6 H6 120.8 . . ? C8 C7 C6 122.5(3) . . ? C8 C7 H7 118.7 . . ? C6 C7 H7 118.7 . . ? C7 C8 C9 120.9(3) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C16 C9 C8 115.8(3) . . ? C16 C9 C10 116.2(3) . . ? C8 C9 C10 128.0(3) . . ? C11 C10 C9 119.7(3) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 123.3(3) . . ? C10 C11 H11 118.4 . . ? C12 C11 H11 118.4 . . ? C13 C12 C11 118.5(3) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C12 C13 C16 118.1(3) . . ? C12 C13 C14 136.4(3) . . ? C16 C13 C14 105.5(2) . . ? C15 C14 C4 118.7(3) . . ? C15 C14 C13 132.4(3) . . ? C4 C14 C13 108.9(2) . . ? N1 C15 C14 120.9(3) . . ? N1 C15 C18 116.3(2) . . ? C14 C15 C18 122.8(3) . . ? C9 C16 C5 124.1(3) . . ? C9 C16 C13 124.3(3) . . ? C5 C16 C13 111.6(2) . . ? C3 C17 H171 109.5 . . ? C3 C17 H172 109.5 . . ? H171 C17 H172 109.5 . . ? C3 C17 H173 109.5 . . ? H171 C17 H173 109.5 . . ? H172 C17 H173 109.5 . . ? C15 C18 H181 109.5 . . ? C15 C18 H182 109.5 . . ? H181 C18 H182 109.5 . . ? C15 C18 H183 109.5 . . ? H181 C18 H183 109.5 . . ? H182 C18 H183 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N1 N2 C3 0.9(4) . . . . ? N1 N2 C3 C4 0.3(4) . . . . ? N1 N2 C3 C17 -179.2(3) . . . . ? N2 C3 C4 C14 -1.7(4) . . . . ? C17 C3 C4 C14 177.8(3) . . . . ? N2 C3 C4 C5 179.0(3) . . . . ? C17 C3 C4 C5 -1.5(5) . . . . ? C3 C4 C5 C6 -4.7(6) . . . . ? C14 C4 C5 C6 175.9(3) . . . . ? C3 C4 C5 C16 178.4(3) . . . . ? C14 C4 C5 C16 -1.0(3) . . . . ? C16 C5 C6 C7 -1.4(4) . . . . ? C4 C5 C6 C7 -177.9(3) . . . . ? C5 C6 C7 C8 0.7(4) . . . . ? C6 C7 C8 C9 0.4(5) . . . . ? C7 C8 C9 C16 -0.7(4) . . . . ? C7 C8 C9 C10 178.5(3) . . . . ? C16 C9 C10 C11 1.8(4) . . . . ? C8 C9 C10 C11 -177.3(3) . . . . ? C9 C10 C11 C12 0.1(5) . . . . ? C10 C11 C12 C13 -1.9(5) . . . . ? C11 C12 C13 C16 1.7(4) . . . . ? C11 C12 C13 C14 179.7(3) . . . . ? C3 C4 C14 C15 1.9(4) . . . . ? C5 C4 C14 C15 -178.6(2) . . . . ? C3 C4 C14 C13 -178.9(2) . . . . ? C5 C4 C14 C13 0.6(3) . . . . ? C12 C13 C14 C15 1.0(5) . . . . ? C16 C13 C14 C15 179.1(3) . . . . ? C12 C13 C14 C4 -178.1(3) . . . . ? C16 C13 C14 C4 0.1(3) . . . . ? N2 N1 C15 C14 -0.7(4) . . . . ? N2 N1 C15 C18 179.5(3) . . . . ? C4 C14 C15 N1 -0.7(4) . . . . ? C13 C14 C15 N1 -179.8(3) . . . . ? C4 C14 C15 C18 179.0(3) . . . . ? C13 C14 C15 C18 0.0(5) . . . . ? C8 C9 C16 C5 -0.1(4) . . . . ? C10 C9 C16 C5 -179.3(2) . . . . ? C8 C9 C16 C13 177.2(2) . . . . ? C10 C9 C16 C13 -2.0(4) . . . . ? C6 C5 C16 C9 1.1(4) . . . . ? C4 C5 C16 C9 178.6(3) . . . . ? C6 C5 C16 C13 -176.5(2) . . . . ? C4 C5 C16 C13 1.1(3) . . . . ? C12 C13 C16 C9 0.3(4) . . . . ? C14 C13 C16 C9 -178.3(3) . . . . ? C12 C13 C16 C5 177.9(2) . . . . ? C14 C13 C16 C5 -0.7(3) . . . . ? # End of CIF ============================================================ # Attachment '7,10-diphenyl-8,9-diazafluoranthene1.cif' data_SG0638 _database_code_depnum_ccdc_archive 'CCDC 710133' _audit_creation_method SHELXL-97 _audit_creation_date 06-10-03 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C26 H16 N2' _chemical_formula_sum 'C26 H16 N2' _chemical_formula_weight 356.43 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 104 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 64 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 8 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.5128(16) _cell_length_b 9.9474(8) _cell_length_c 7.9414(6) _cell_angle_alpha 90.00 _cell_angle_beta 103.717(5) _cell_angle_gamma 90.00 _cell_volume 1727.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 1617 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.0806 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: acetone Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.463(4) Frames collected: 174 Seconds exposure per frame: 80 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 10175 _diffrn_reflns_av_R_equivalents 0.1290 _diffrn_reflns_av_sigmaI/netI 0.0878 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.06 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 1531 _reflns_number_gt 996 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+1.0758P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0073(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1531 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0965 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1445 _refine_ls_wR_factor_gt 0.1195 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.370 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.091 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.47205(9) 0.6021(2) 0.2652(3) 0.0257(6) Uani 1 1 d . . . C2 C 0.44336(11) 0.7178(3) 0.2840(3) 0.0205(7) Uani 1 1 d . . . C3 C 0.47124(11) 0.8414(2) 0.2714(3) 0.0193(6) Uani 1 1 d . . . C4 C 0.45332(11) 0.9823(3) 0.2912(3) 0.0189(6) Uani 1 1 d . . . C5 C 0.40589(11) 1.0478(3) 0.3401(3) 0.0221(7) Uani 1 1 d . . . H5 H 0.3740 0.9983 0.3714 0.027 Uiso 1 1 calc R . . C6 C 0.40570(12) 1.1894(3) 0.3428(3) 0.0241(7) Uani 1 1 d . . . H6 H 0.3730 1.2340 0.3763 0.029 Uiso 1 1 calc R . . C7 C 0.45050(11) 1.2661(3) 0.2994(3) 0.0219(7) Uani 1 1 d . . . H7 H 0.4483 1.3614 0.3024 0.026 Uiso 1 1 calc R . . C8 C 0.5000 1.2024(4) 0.2500 0.0203(9) Uani 1 2 d S . . C9 C 0.5000 1.0623(3) 0.2500 0.0178(9) Uani 1 2 d S . . C10 C 0.38156(11) 0.6961(2) 0.3143(3) 0.0207(7) Uani 1 1 d . . . C11 C 0.37261(12) 0.5948(3) 0.4273(3) 0.0250(7) Uani 1 1 d . . . H11 H 0.4066 0.5442 0.4893 0.030 Uiso 1 1 calc R . . C12 C 0.31474(12) 0.5674(3) 0.4499(3) 0.0294(7) Uani 1 1 d . . . H12 H 0.3093 0.4991 0.5286 0.035 Uiso 1 1 calc R . . C13 C 0.26474(13) 0.6389(3) 0.3584(4) 0.0308(8) Uani 1 1 d . . . H13 H 0.2250 0.6195 0.3735 0.037 Uiso 1 1 calc R . . C14 C 0.27282(12) 0.7386(3) 0.2449(4) 0.0284(7) Uani 1 1 d . . . H14 H 0.2385 0.7875 0.1814 0.034 Uiso 1 1 calc R . . C15 C 0.33097(12) 0.7678(3) 0.2230(3) 0.0251(7) Uani 1 1 d . . . H15 H 0.3362 0.8370 0.1453 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0263(12) 0.0169(14) 0.0347(14) 0.0023(11) 0.0088(11) 0.0023(10) C2 0.0253(15) 0.0153(15) 0.0191(15) -0.0003(11) 0.0019(11) -0.0011(12) C3 0.0228(14) 0.0164(15) 0.0173(14) 0.0002(11) 0.0017(11) 0.0007(11) C4 0.0209(13) 0.0177(15) 0.0166(14) 0.0015(11) 0.0015(11) 0.0006(11) C5 0.0248(15) 0.0220(17) 0.0198(15) 0.0013(12) 0.0058(12) -0.0003(12) C6 0.0285(16) 0.0183(16) 0.0258(16) -0.0011(12) 0.0073(12) 0.0055(12) C7 0.0297(15) 0.0120(14) 0.0227(15) -0.0006(11) 0.0032(12) 0.0034(12) C8 0.027(2) 0.017(2) 0.016(2) 0.000 0.0013(16) 0.000 C9 0.023(2) 0.015(2) 0.0133(19) 0.000 0.0016(15) 0.000 C10 0.0240(15) 0.0143(14) 0.0220(15) -0.0049(12) 0.0022(12) -0.0035(11) C11 0.0299(16) 0.0176(16) 0.0266(16) -0.0020(12) 0.0048(12) -0.0035(12) C12 0.0368(18) 0.0230(16) 0.0294(17) 0.0008(13) 0.0101(13) -0.0102(13) C13 0.0282(16) 0.0319(18) 0.0342(17) -0.0037(14) 0.0112(13) -0.0064(13) C14 0.0254(16) 0.0280(17) 0.0308(17) -0.0018(13) 0.0048(12) 0.0007(12) C15 0.0289(15) 0.0202(16) 0.0269(16) 0.0007(13) 0.0082(12) -0.0029(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N1 1.336(4) 2_655 ? N1 C2 1.345(3) . ? C2 C3 1.395(3) . ? C2 C10 1.483(4) . ? C3 C3 1.414(5) 2_655 ? C3 C4 1.477(4) . ? C4 C5 1.383(3) . ? C4 C9 1.417(3) . ? C5 C6 1.409(4) . ? C5 H5 0.9500 . ? C6 C7 1.372(4) . ? C6 H6 0.9500 . ? C7 C8 1.416(3) . ? C7 H7 0.9500 . ? C8 C9 1.393(5) . ? C10 C15 1.393(4) . ? C10 C11 1.395(4) . ? C11 C12 1.384(4) . ? C11 H11 0.9500 . ? C12 C13 1.383(4) . ? C12 H12 0.9500 . ? C13 C14 1.381(4) . ? C13 H13 0.9500 . ? C14 C15 1.391(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 N1 C2 121.17(14) 2_655 . ? N1 C2 C3 120.7(2) . . ? N1 C2 C10 112.7(2) . . ? C3 C2 C10 126.6(2) . . ? C2 C3 C3 118.06(15) . 2_655 ? C2 C3 C4 133.6(2) . . ? C3 C3 C4 108.33(13) 2_655 . ? C5 C4 C9 117.7(2) . . ? C5 C4 C3 136.5(2) . . ? C9 C4 C3 105.8(2) . . ? C4 C5 C6 118.7(2) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C7 C6 C5 123.1(3) . . ? C7 C6 H6 118.4 . . ? C5 C6 H6 118.4 . . ? C6 C7 C8 119.7(3) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C9 C8 C7 116.57(17) . . ? C7 C8 C7 126.9(3) . 2_655 ? C8 C9 C4 124.18(16) . . ? C4 C9 C4 111.6(3) 2_655 . ? C15 C10 C11 118.7(2) . . ? C15 C10 C2 121.5(2) . . ? C11 C10 C2 119.6(2) . . ? C12 C11 C10 120.7(2) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C13 C12 C11 120.3(3) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 119.7(3) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.3(3) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C10 120.4(3) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 N1 C2 C3 0.3(4) 2_655 . . . ? N1 N1 C2 C10 179.2(3) 2_655 . . . ? N1 C2 C3 C3 3.5(4) . . . 2_655 ? C10 C2 C3 C3 -175.2(3) . . . 2_655 ? N1 C2 C3 C4 -177.5(3) . . . . ? C10 C2 C3 C4 3.8(4) . . . . ? C2 C3 C4 C5 5.5(5) . . . . ? C3 C3 C4 C5 -175.5(3) 2_655 . . . ? C2 C3 C4 C9 -176.0(2) . . . . ? C3 C3 C4 C9 3.0(3) 2_655 . . . ? C9 C4 C5 C6 1.4(3) . . . . ? C3 C4 C5 C6 179.7(3) . . . . ? C4 C5 C6 C7 -0.1(4) . . . . ? C5 C6 C7 C8 -0.4(4) . . . . ? C6 C7 C8 C9 -0.4(3) . . . . ? C6 C7 C8 C7 179.6(3) . . . 2_655 ? C7 C8 C9 C4 -178.22(16) . . . 2_655 ? C7 C8 C9 C4 1.78(16) 2_655 . . 2_655 ? C7 C8 C9 C4 1.78(16) . . . . ? C7 C8 C9 C4 -178.22(16) 2_655 . . . ? C5 C4 C9 C8 -2.3(2) . . . . ? C3 C4 C9 C8 178.88(11) . . . . ? C5 C4 C9 C4 177.7(2) . . . 2_655 ? C3 C4 C9 C4 -1.12(11) . . . 2_655 ? N1 C2 C10 C15 -132.7(3) . . . . ? C3 C2 C10 C15 46.1(4) . . . . ? N1 C2 C10 C11 42.5(3) . . . . ? C3 C2 C10 C11 -138.7(3) . . . . ? C15 C10 C11 C12 -0.9(4) . . . . ? C2 C10 C11 C12 -176.2(2) . . . . ? C10 C11 C12 C13 1.0(4) . . . . ? C11 C12 C13 C14 -0.4(4) . . . . ? C12 C13 C14 C15 -0.3(4) . . . . ? C13 C14 C15 C10 0.5(4) . . . . ? C11 C10 C15 C14 0.1(4) . . . . ? C2 C10 C15 C14 175.3(2) . . . . ? # End of CIF ============================================================ # Attachment '7,10-methyl-ester-1,6-dimethyl-8,9-diazafluoran.cif' data_SG0605 _database_code_depnum_ccdc_archive 'CCDC 710134' _audit_creation_method SHELXL-97 _audit_creation_date 06-01-24 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C20 H16 N2 O4' _chemical_formula_sum 'C20 H16 N2 O4' _chemical_formula_weight 348.36 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 80 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 64 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 8 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 16 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'C 2 2 21 ' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 20 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, -z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, -z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' _cell_length_a 8.3958(2) _cell_length_b 9.9699(2) _cell_length_c 19.6247(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1642.69(7) _cell_formula_units_Z 4 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 1091 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.0995 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: dichloromethane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.549(1) Frames collected: 417 Seconds exposure per frame: 30 Degrees rotation per frame: 1.0 Crystal-Detector distance (mm): 30.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 12353 _diffrn_reflns_av_R_equivalents 0.0570 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.46 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 1086 _reflns_number_gt 1000 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2005)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.7644P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.127(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 1(2) _chemical_absolute_configuration ? _refine_ls_number_reflns 1085 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1135 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.229 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.062 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O10 O 0.9313(2) 0.33729(17) 0.56913(8) 0.0317(5) Uani 1 1 d . . . O11 O 0.7437(2) 0.20711(19) 0.61734(8) 0.0357(5) Uani 1 1 d . . . N1 N 0.9650(2) 0.19717(19) 0.71955(9) 0.0269(5) Uani 1 1 d . . . C2 C 0.9252(3) 0.3139(2) 0.69002(10) 0.0240(5) Uani 1 1 d . . . C3 C 0.9552(3) 0.4390(2) 0.71926(11) 0.0228(5) Uani 1 1 d . . . C4 C 0.9185(3) 0.5785(2) 0.70117(11) 0.0236(5) Uani 1 1 d . . . C5 C 0.8237(3) 0.6411(2) 0.65277(12) 0.0275(5) Uani 1 1 d . . . C6 C 0.8228(3) 0.7848(3) 0.65341(12) 0.0310(6) Uani 1 1 d . . . H6 H 0.7601 0.8301 0.6203 0.037 Uiso 1 1 calc R . . C7 C 0.9073(3) 0.8605(2) 0.69921(12) 0.0315(6) Uani 1 1 d . . . H7 H 0.9037 0.9556 0.6968 0.038 Uiso 1 1 calc R . . C8 C 1.0000 0.7968(3) 0.7500 0.0275(7) Uani 1 2 d S . . C9 C 1.0000 0.6562(3) 0.7500 0.0257(7) Uani 1 2 d S . . C10 C 0.8667(3) 0.2908(2) 0.61862(11) 0.0257(5) Uani 1 1 d . . . C12 C 0.6840(4) 0.1711(4) 0.55075(14) 0.0485(8) Uani 1 1 d . . . H121 H 0.7727 0.1415 0.5219 0.073 Uiso 1 1 calc R . . H122 H 0.6324 0.2491 0.5299 0.073 Uiso 1 1 calc R . . H123 H 0.6065 0.0982 0.5552 0.073 Uiso 1 1 calc R . . C13 C 0.7192(3) 0.5715(2) 0.60209(12) 0.0315(6) Uani 1 1 d . . . H131 H 0.6727 0.4913 0.6230 0.047 Uiso 1 1 calc R . . H132 H 0.7826 0.5454 0.5623 0.047 Uiso 1 1 calc R . . H133 H 0.6338 0.6323 0.5878 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O10 0.0343(9) 0.0351(9) 0.0258(8) 0.0015(6) 0.0021(7) 0.0021(7) O11 0.0390(10) 0.0420(10) 0.0260(8) -0.0034(8) -0.0029(7) -0.0114(9) N1 0.0322(10) 0.0224(9) 0.0260(9) 0.0001(7) -0.0019(8) -0.0007(8) C2 0.0245(10) 0.0243(11) 0.0232(10) -0.0003(8) 0.0007(8) 0.0003(9) C3 0.0231(10) 0.0234(10) 0.0220(10) 0.0008(8) 0.0020(9) -0.0001(8) C4 0.0250(11) 0.0203(10) 0.0255(10) 0.0004(8) 0.0046(10) 0.0008(8) C5 0.0284(12) 0.0289(12) 0.0251(11) 0.0029(9) 0.0045(10) 0.0036(9) C6 0.0338(12) 0.0271(12) 0.0322(12) 0.0058(10) 0.0050(10) 0.0067(10) C7 0.0353(13) 0.0245(11) 0.0348(13) 0.0049(9) 0.0080(12) 0.0032(9) C8 0.0280(15) 0.0220(15) 0.0325(15) 0.000 0.0072(13) 0.000 C9 0.0262(15) 0.0235(15) 0.0275(15) 0.000 0.0053(13) 0.000 C10 0.0281(11) 0.0243(10) 0.0248(10) -0.0018(9) -0.0007(8) 0.0031(9) C12 0.0521(18) 0.0629(19) 0.0305(13) -0.0112(13) -0.0079(12) -0.0159(16) C13 0.0324(13) 0.0308(12) 0.0313(12) 0.0003(10) -0.0036(10) 0.0072(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O10 C10 1.205(3) . ? O11 C10 1.328(3) . ? O11 C12 1.445(3) . ? N1 N1 1.332(4) 4_756 ? N1 C2 1.343(3) . ? C2 C3 1.396(3) . ? C2 C10 1.502(3) . ? C3 C3 1.422(4) 4_756 ? C3 C4 1.468(3) . ? C4 C5 1.387(3) . ? C4 C9 1.410(3) . ? C5 C6 1.433(3) . ? C5 C13 1.497(3) . ? C6 C7 1.372(4) . ? C6 H6 0.9500 . ? C7 C8 1.415(3) . ? C7 H7 0.9500 . ? C8 C9 1.402(4) . ? C12 H121 0.9800 . ? C12 H122 0.9800 . ? C12 H123 0.9800 . ? C13 H131 0.9800 . ? C13 H132 0.9800 . ? C13 H133 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 O11 C12 116.3(2) . . ? N1 N1 C2 119.81(12) 4_756 . ? N1 C2 C3 123.52(19) . . ? N1 C2 C10 110.53(19) . . ? C3 C2 C10 125.4(2) . . ? C2 C3 C3 116.39(13) . 4_756 ? C2 C3 C4 135.2(2) . . ? C3 C3 C4 108.44(12) 4_756 . ? C5 C4 C9 119.8(2) . . ? C5 C4 C3 135.4(2) . . ? C9 C4 C3 104.7(2) . . ? C4 C5 C6 116.5(2) . . ? C4 C5 C13 125.7(2) . . ? C6 C5 C13 117.8(2) . . ? C7 C6 C5 123.6(2) . . ? C7 C6 H6 118.2 . . ? C5 C6 H6 118.2 . . ? C6 C7 C8 119.9(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 116.67(15) . . ? C7 C8 C7 126.7(3) . 4_756 ? C8 C9 C4 123.35(14) . . ? C4 C9 C4 113.3(3) . 4_756 ? O10 C10 O11 125.2(2) . . ? O10 C10 C2 123.1(2) . . ? O11 C10 C2 111.60(18) . . ? O11 C12 H121 109.5 . . ? O11 C12 H122 109.5 . . ? H121 C12 H122 109.5 . . ? O11 C12 H123 109.5 . . ? H121 C12 H123 109.5 . . ? H122 C12 H123 109.5 . . ? C5 C13 H131 109.5 . . ? C5 C13 H132 109.5 . . ? H131 C13 H132 109.5 . . ? C5 C13 H133 109.5 . . ? H131 C13 H133 109.5 . . ? H132 C13 H133 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 N1 C2 C3 1.0(4) 4_756 . . . ? N1 N1 C2 C10 173.1(2) 4_756 . . . ? N1 C2 C3 C3 5.5(4) . . . 4_756 ? C10 C2 C3 C3 -165.4(2) . . . 4_756 ? N1 C2 C3 C4 -176.0(3) . . . . ? C10 C2 C3 C4 13.1(4) . . . . ? C2 C3 C4 C5 9.6(5) . . . . ? C3 C3 C4 C5 -171.8(3) 4_756 . . . ? C2 C3 C4 C9 -173.8(2) . . . . ? C3 C3 C4 C9 4.8(3) 4_756 . . . ? C9 C4 C5 C6 3.6(3) . . . . ? C3 C4 C5 C6 179.8(2) . . . . ? C9 C4 C5 C13 -174.14(19) . . . . ? C3 C4 C5 C13 2.1(4) . . . . ? C4 C5 C6 C7 -1.0(4) . . . . ? C13 C5 C6 C7 176.9(2) . . . . ? C5 C6 C7 C8 -1.0(4) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? C6 C7 C8 C7 -179.7(2) . . . 4_756 ? C7 C8 C9 C4 2.44(16) . . . . ? C7 C8 C9 C4 -177.56(16) . . . 4_756 ? C5 C4 C9 C8 -4.5(2) . . . . ? C3 C4 C9 C8 178.21(10) . . . . ? C5 C4 C9 C4 175.5(2) . . . 4_756 ? C3 C4 C9 C4 -1.79(10) . . . 4_756 ? C12 O11 C10 O10 -0.4(4) . . . . ? C12 O11 C10 C2 -176.3(2) . . . . ? N1 C2 C10 O10 -118.8(3) . . . . ? C3 C2 C10 O10 53.1(3) . . . . ? N1 C2 C10 O11 57.2(3) . . . . ? C3 C2 C10 O11 -130.9(2) . . . . ? # End of CIF ============================================================ # Attachment '7,10-methyl-ester-1,6-dimethyl-8,9-diazafluorant.cif' data_SG0631 _database_code_depnum_ccdc_archive 'CCDC 710135' _audit_creation_method SHELXL-97 _audit_creation_date 06-09-13 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C18 H12 N2 O4' _chemical_formula_sum 'C18 H12 N2 O4' _chemical_formula_weight 320.30 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 72 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 48 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 8 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 16 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.9472(2) _cell_length_b 13.2994(2) _cell_length_c 11.5775(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.6580(8) _cell_angle_gamma 90.00 _cell_volume 1391.95(4) _cell_formula_units_Z 4 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 4232 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: hexane / acetone Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.511(1) Frames collected: 450 Seconds exposure per frame: 72 Degrees rotation per frame: 1.8 Crystal-Detector distance (mm): 32.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 39027 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 30.03 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 4226 _reflns_number_gt 3767 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'Shake-and-Bake (Miller et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+0.2875P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.121(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack & Bernardinelli (2000), ? Friedel pairs' _refine_ls_abs_structure_Flack -0.4(10) _chemical_absolute_configuration ? _refine_ls_number_reflns 4226 _refine_ls_number_parameters 438 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1187 _refine_ls_wR_factor_gt 0.1138 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.464 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.076 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O17 O 0.97511(19) 0.12062(17) 0.71482(15) 0.0346(4) Uani 1 1 d . . . O18 O 1.16238(17) 0.17586(15) 0.67280(14) 0.0279(4) Uani 1 1 d . . . O20 O 0.62765(18) 0.1517(2) 0.02591(15) 0.0437(5) Uani 1 1 d . . . O21 O 0.86706(17) 0.15394(17) 0.06837(14) 0.0284(4) Uani 1 1 d . . . N1 N 0.95350(19) 0.16143(17) 0.30748(16) 0.0221(4) Uani 1 1 d . . . N2 N 1.01654(19) 0.16007(17) 0.43305(16) 0.0220(4) Uani 1 1 d . . . C3 C 0.9323(2) 0.15518(17) 0.49874(18) 0.0179(4) Uani 1 1 d . . . C4 C 0.7784(2) 0.15428(17) 0.44075(17) 0.0165(3) Uani 1 1 d . . . C5 C 0.6610(2) 0.15505(17) 0.48587(18) 0.0170(4) Uani 1 1 d . . . C6 C 0.6544(2) 0.15528(18) 0.60287(19) 0.0198(4) Uani 1 1 d . . . H6 H 0.7426 0.1548 0.6791 0.024 Uiso 1 1 calc R . . C7 C 0.5144(2) 0.1563(2) 0.60751(19) 0.0228(4) Uani 1 1 d . . . H7 H 0.5107 0.1566 0.6882 0.027 Uiso 1 1 calc R . . C8 C 0.3828(2) 0.1569(2) 0.4995(2) 0.0228(4) Uani 1 1 d . . . H8 H 0.2908 0.1579 0.5062 0.027 Uiso 1 1 calc R . . C9 C 0.3871(2) 0.15588(17) 0.37817(19) 0.0190(4) Uani 1 1 d . . . C10 C 0.2622(2) 0.1540(2) 0.2591(2) 0.0234(4) Uani 1 1 d . . . H10 H 0.1650 0.1540 0.2554 0.028 Uiso 1 1 calc R . . C11 C 0.2836(2) 0.1523(2) 0.1487(2) 0.0253(4) Uani 1 1 d . . . H11 H 0.1993 0.1505 0.0696 0.030 Uiso 1 1 calc R . . C12 C 0.4258(2) 0.1530(2) 0.14828(19) 0.0222(4) Uani 1 1 d . . . H12 H 0.4362 0.1522 0.0704 0.027 Uiso 1 1 calc R . . C13 C 0.5487(2) 0.15486(17) 0.26256(17) 0.0175(4) Uani 1 1 d . . . C14 C 0.7104(2) 0.15491(17) 0.30449(17) 0.0160(3) Uani 1 1 d . . . C15 C 0.8057(2) 0.15692(17) 0.24324(18) 0.0177(4) Uani 1 1 d . . . C16 C 0.5267(2) 0.15518(17) 0.37565(18) 0.0174(3) Uani 1 1 d . . . C17 C 1.0226(2) 0.14910(19) 0.64016(19) 0.0209(4) Uani 1 1 d . . . C19 C 1.2570(3) 0.1698(2) 0.8070(2) 0.0353(6) Uani 1 1 d . . . H191 H 1.2220 0.2168 0.8535 0.053 Uiso 1 1 calc R . . H192 H 1.3586 0.1871 0.8214 0.053 Uiso 1 1 calc R . . H193 H 1.2548 0.1012 0.8370 0.053 Uiso 1 1 calc R . . C20 C 0.7547(2) 0.15415(19) 0.10140(17) 0.0204(4) Uani 1 1 d . . . C22 C 0.8259(3) 0.1496(2) -0.06678(19) 0.0299(5) Uani 1 1 d . . . H221 H 0.7570 0.0938 -0.1037 0.045 Uiso 1 1 calc R . . H222 H 0.9146 0.1393 -0.0822 0.045 Uiso 1 1 calc R . . H223 H 0.7782 0.2129 -0.1061 0.045 Uiso 1 1 calc R . . O47 O 0.64031(18) 0.93086(15) 0.74052(14) 0.0297(4) Uani 1 1 d . . . O48 O 0.82541(17) 0.88184(14) 0.69106(14) 0.0257(4) Uani 1 1 d . . . O50 O 0.29099(18) 0.8969(2) 0.04638(15) 0.0425(5) Uani 1 1 d . . . O51 O 0.53055(17) 0.90575(18) 0.09165(13) 0.0313(4) Uani 1 1 d . . . N31 N 0.61474(18) 0.90439(16) 0.32925(15) 0.0211(3) Uani 1 1 d . . . N32 N 0.67800(19) 0.90519(18) 0.45471(15) 0.0212(4) Uani 1 1 d . . . C33 C 0.5952(2) 0.90644(17) 0.52158(17) 0.0168(3) Uani 1 1 d . . . C34 C 0.4406(2) 0.90694(17) 0.46318(17) 0.0158(3) Uani 1 1 d . . . C35 C 0.3227(2) 0.90759(17) 0.50888(17) 0.0167(4) Uani 1 1 d . . . C36 C 0.3166(2) 0.91095(19) 0.62560(19) 0.0212(4) Uani 1 1 d . . . H36 H 0.4046 0.9136 0.7019 0.025 Uiso 1 1 calc R . . C37 C 0.1754(2) 0.91041(19) 0.62905(19) 0.0234(4) Uani 1 1 d . . . H37 H 0.1711 0.9117 0.7095 0.028 Uiso 1 1 calc R . . C38 C 0.0444(2) 0.90817(19) 0.5213(2) 0.0234(4) Uani 1 1 d . . . H38 H -0.0475 0.9077 0.5281 0.028 Uiso 1 1 calc R . . C39 C 0.0480(2) 0.90650(18) 0.39991(19) 0.0206(4) Uani 1 1 d . . . C40 C -0.0762(2) 0.9063(2) 0.2806(2) 0.0242(4) Uani 1 1 d . . . H40 H -0.1735 0.9067 0.2766 0.029 Uiso 1 1 calc R . . C41 C -0.0546(2) 0.9056(2) 0.1704(2) 0.0263(4) Uani 1 1 d . . . H41 H -0.1390 0.9058 0.0913 0.032 Uiso 1 1 calc R . . C42 C 0.0874(2) 0.9045(2) 0.1697(2) 0.0226(4) Uani 1 1 d . . . H42 H 0.0980 0.9037 0.0918 0.027 Uiso 1 1 calc R . . C43 C 0.2107(2) 0.90471(17) 0.28527(17) 0.0177(4) Uani 1 1 d . . . C44 C 0.3721(2) 0.90474(17) 0.32658(17) 0.0167(3) Uani 1 1 d . . . C45 C 0.4669(2) 0.90372(18) 0.26521(16) 0.0178(4) Uani 1 1 d . . . C46 C 0.1878(2) 0.90597(17) 0.39794(17) 0.0176(3) Uani 1 1 d . . . C47 C 0.6862(2) 0.90797(18) 0.66307(17) 0.0189(4) Uani 1 1 d . . . C49 C 0.9255(3) 0.8841(2) 0.8240(2) 0.0282(5) Uani 1 1 d . . . H491 H 0.9539 0.9538 0.8504 0.042 Uiso 1 1 calc R . . H492 H 1.0140 0.8446 0.8375 0.042 Uiso 1 1 calc R . . H493 H 0.8765 0.8553 0.8743 0.042 Uiso 1 1 calc R . . C50 C 0.4170(2) 0.90193(19) 0.12305(17) 0.0205(4) Uani 1 1 d . . . C52 C 0.4928(3) 0.9062(3) -0.04262(19) 0.0310(5) Uani 1 1 d . . . H521 H 0.4220 0.8522 -0.0838 0.047 Uiso 1 1 calc R . . H522 H 0.5824 0.8957 -0.0567 0.047 Uiso 1 1 calc R . . H523 H 0.4484 0.9711 -0.0788 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O17 0.0243(8) 0.0598(12) 0.0203(7) 0.0092(7) 0.0098(6) 0.0010(8) O18 0.0173(7) 0.0453(11) 0.0175(7) -0.0013(7) 0.0037(6) -0.0030(7) O20 0.0189(7) 0.0920(16) 0.0183(7) -0.0055(10) 0.0057(6) -0.0067(10) O21 0.0212(7) 0.0501(10) 0.0168(7) -0.0029(8) 0.0108(6) -0.0005(8) N1 0.0148(8) 0.0340(10) 0.0179(8) -0.0017(8) 0.0072(7) -0.0013(8) N2 0.0174(8) 0.0322(9) 0.0175(8) -0.0010(8) 0.0084(7) 0.0009(8) C3 0.0148(8) 0.0221(9) 0.0177(8) 0.0001(8) 0.0077(7) -0.0005(8) C4 0.0148(8) 0.0191(8) 0.0170(8) 0.0011(8) 0.0080(7) 0.0006(8) C5 0.0160(8) 0.0186(8) 0.0183(9) 0.0005(8) 0.0090(7) 0.0003(8) C6 0.0194(9) 0.0230(9) 0.0197(9) 0.0005(8) 0.0109(7) 0.0007(9) C7 0.0239(9) 0.0279(10) 0.0226(9) 0.0001(9) 0.0156(8) -0.0010(9) C8 0.0231(10) 0.0247(9) 0.0282(10) 0.0010(10) 0.0181(9) 0.0004(10) C9 0.0150(8) 0.0200(9) 0.0247(9) 0.0009(9) 0.0109(7) -0.0001(8) C10 0.0141(8) 0.0279(10) 0.0285(10) 0.0000(9) 0.0092(8) -0.0002(9) C11 0.0140(8) 0.0362(11) 0.0229(9) 0.0019(10) 0.0048(7) -0.0013(9) C12 0.0154(8) 0.0296(10) 0.0206(9) 0.0016(9) 0.0067(7) 0.0000(9) C13 0.0135(8) 0.0217(9) 0.0181(8) 0.0010(9) 0.0072(7) -0.0006(8) C14 0.0127(7) 0.0202(8) 0.0157(8) -0.0003(8) 0.0066(6) -0.0010(7) C15 0.0147(8) 0.0228(9) 0.0166(8) -0.0007(8) 0.0075(7) -0.0020(8) C16 0.0147(8) 0.0195(8) 0.0207(8) 0.0005(8) 0.0098(7) 0.0003(8) C17 0.0165(9) 0.0269(10) 0.0187(9) 0.0000(9) 0.0065(8) 0.0020(9) C19 0.0223(10) 0.0532(17) 0.0207(10) -0.0027(11) -0.0006(8) 0.0010(12) C20 0.0185(8) 0.0270(10) 0.0175(8) -0.0021(9) 0.0092(7) -0.0008(9) C22 0.0316(11) 0.0459(14) 0.0158(9) -0.0016(10) 0.0134(8) -0.0004(12) O47 0.0224(7) 0.0491(11) 0.0182(7) -0.0027(7) 0.0091(6) 0.0040(7) O48 0.0148(7) 0.0430(10) 0.0165(6) -0.0009(6) 0.0038(5) 0.0041(6) O50 0.0189(7) 0.0893(17) 0.0175(7) -0.0080(10) 0.0057(6) -0.0069(11) O51 0.0203(7) 0.0601(12) 0.0158(7) 0.0000(9) 0.0098(6) -0.0009(9) N31 0.0154(7) 0.0325(9) 0.0160(7) 0.0002(8) 0.0070(6) 0.0008(8) N32 0.0164(8) 0.0321(9) 0.0156(7) -0.0010(8) 0.0074(6) 0.0001(8) C33 0.0141(8) 0.0218(8) 0.0146(7) 0.0008(8) 0.0062(6) 0.0001(8) C34 0.0137(8) 0.0203(8) 0.0140(7) 0.0001(8) 0.0064(6) 0.0004(8) C35 0.0157(8) 0.0184(8) 0.0190(8) 0.0003(8) 0.0101(7) 0.0009(9) C36 0.0220(9) 0.0256(10) 0.0199(8) -0.0007(9) 0.0126(7) 0.0009(9) C37 0.0227(10) 0.0293(10) 0.0241(9) -0.0013(9) 0.0156(8) -0.0010(10) C38 0.0222(9) 0.0256(9) 0.0289(10) -0.0007(10) 0.0170(8) -0.0013(10) C39 0.0171(9) 0.0212(9) 0.0271(9) -0.0010(9) 0.0128(8) -0.0001(9) C40 0.0145(8) 0.0276(10) 0.0308(10) -0.0014(10) 0.0098(8) -0.0016(10) C41 0.0140(8) 0.0382(12) 0.0248(9) -0.0006(11) 0.0062(7) -0.0012(10) C42 0.0148(8) 0.0322(10) 0.0196(8) 0.0005(10) 0.0059(7) 0.0011(10) C43 0.0127(8) 0.0216(9) 0.0191(8) 0.0004(9) 0.0069(7) -0.0006(9) C44 0.0143(8) 0.0209(8) 0.0149(7) -0.0003(8) 0.0061(6) 0.0003(8) C45 0.0152(8) 0.0241(9) 0.0139(7) -0.0010(8) 0.0060(6) -0.0010(8) C46 0.0148(8) 0.0201(8) 0.0196(8) -0.0010(9) 0.0087(7) -0.0011(9) C47 0.0173(8) 0.0234(9) 0.0156(8) -0.0001(8) 0.0065(7) -0.0001(9) C49 0.0212(10) 0.0396(13) 0.0160(9) 0.0003(9) 0.0001(8) 0.0004(9) C50 0.0189(8) 0.0267(10) 0.0168(8) -0.0008(9) 0.0085(7) 0.0010(9) C52 0.0311(11) 0.0489(14) 0.0166(9) 0.0004(11) 0.0134(8) 0.0001(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O17 C17 1.206(3) . ? O18 C17 1.329(2) . ? O18 C19 1.444(3) . ? O20 C20 1.200(3) . ? O21 C20 1.324(2) . ? O21 C22 1.444(2) . ? N1 N2 1.322(2) . ? N1 C15 1.344(2) . ? N2 C3 1.348(2) . ? C3 C4 1.392(2) . ? C3 C17 1.506(3) . ? C4 C14 1.434(2) . ? C4 C5 1.465(2) . ? C5 C6 1.383(2) . ? C5 C16 1.411(3) . ? C6 C7 1.416(3) . ? C6 H6 0.9500 . ? C7 C8 1.383(3) . ? C7 H7 0.9500 . ? C8 C9 1.423(3) . ? C8 H8 0.9500 . ? C9 C16 1.401(2) . ? C9 C10 1.420(3) . ? C10 C11 1.380(3) . ? C10 H10 0.9500 . ? C11 C12 1.416(3) . ? C11 H11 0.9500 . ? C12 C13 1.377(3) . ? C12 H12 0.9500 . ? C13 C16 1.415(2) . ? C13 C14 1.473(2) . ? C14 C15 1.401(2) . ? C15 C20 1.503(2) . ? C19 H191 0.9800 . ? C19 H192 0.9800 . ? C19 H193 0.9800 . ? C22 H221 0.9800 . ? C22 H222 0.9800 . ? C22 H223 0.9800 . ? O47 C47 1.202(2) . ? O48 C47 1.330(2) . ? O48 C49 1.443(2) . ? O50 C50 1.198(3) . ? O51 C50 1.324(2) . ? O51 C52 1.439(2) . ? N31 N32 1.320(2) . ? N31 C45 1.343(2) . ? N32 C33 1.345(2) . ? C33 C34 1.398(3) . ? C33 C47 1.505(2) . ? C34 C44 1.438(2) . ? C34 C35 1.474(2) . ? C35 C36 1.379(2) . ? C35 C46 1.419(3) . ? C36 C37 1.422(3) . ? C36 H36 0.9500 . ? C37 C38 1.378(3) . ? C37 H37 0.9500 . ? C38 C39 1.421(3) . ? C38 H38 0.9500 . ? C39 C46 1.400(3) . ? C39 C40 1.418(3) . ? C40 C41 1.379(3) . ? C40 H40 0.9500 . ? C41 C42 1.416(3) . ? C41 H41 0.9500 . ? C42 C43 1.388(3) . ? C42 H42 0.9500 . ? C43 C46 1.415(2) . ? C43 C44 1.472(3) . ? C44 C45 1.397(3) . ? C45 C50 1.508(2) . ? C49 H491 0.9800 . ? C49 H492 0.9800 . ? C49 H493 0.9800 . ? C52 H521 0.9800 . ? C52 H522 0.9800 . ? C52 H523 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C17 O18 C19 115.23(18) . . ? C20 O21 C22 114.92(16) . . ? N2 N1 C15 121.04(17) . . ? N1 N2 C3 120.00(18) . . ? N2 C3 C4 123.09(18) . . ? N2 C3 C17 112.79(17) . . ? C4 C3 C17 124.11(16) . . ? C3 C4 C14 116.72(16) . . ? C3 C4 C5 135.09(17) . . ? C14 C4 C5 108.18(16) . . ? C6 C5 C16 118.19(17) . . ? C6 C5 C4 136.02(18) . . ? C16 C5 C4 105.79(16) . . ? C5 C6 C7 119.08(18) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C8 C7 C6 122.75(18) . . ? C8 C7 H7 118.6 . . ? C6 C7 H7 118.6 . . ? C7 C8 C9 119.02(18) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C16 C9 C10 116.93(17) . . ? C16 C9 C8 117.34(18) . . ? C10 C9 C8 125.72(18) . . ? C11 C10 C9 119.25(18) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 122.89(18) . . ? C10 C11 H11 118.6 . . ? C12 C11 H11 118.6 . . ? C13 C12 C11 118.96(18) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C16 118.12(17) . . ? C12 C13 C14 136.55(17) . . ? C16 C13 C14 105.32(15) . . ? C15 C14 C4 116.67(17) . . ? C15 C14 C13 135.17(17) . . ? C4 C14 C13 108.15(15) . . ? N1 C15 C14 122.40(18) . . ? N1 C15 C20 113.45(16) . . ? C14 C15 C20 124.16(17) . . ? C9 C16 C5 123.61(17) . . ? C9 C16 C13 123.83(18) . . ? C5 C16 C13 112.56(16) . . ? O17 C17 O18 123.83(19) . . ? O17 C17 C3 124.23(19) . . ? O18 C17 C3 111.91(17) . . ? O18 C19 H191 109.5 . . ? O18 C19 H192 109.5 . . ? H191 C19 H192 109.5 . . ? O18 C19 H193 109.5 . . ? H191 C19 H193 109.5 . . ? H192 C19 H193 109.5 . . ? O20 C20 O21 123.31(17) . . ? O20 C20 C15 124.66(18) . . ? O21 C20 C15 112.03(16) . . ? O21 C22 H221 109.5 . . ? O21 C22 H222 109.5 . . ? H221 C22 H222 109.5 . . ? O21 C22 H223 109.5 . . ? H221 C22 H223 109.5 . . ? H222 C22 H223 109.5 . . ? C47 O48 C49 116.06(17) . . ? C50 O51 C52 115.40(16) . . ? N32 N31 C45 121.14(17) . . ? N31 N32 C33 120.53(17) . . ? N32 C33 C34 122.39(17) . . ? N32 C33 C47 113.08(16) . . ? C34 C33 C47 124.53(17) . . ? C33 C34 C44 116.94(17) . . ? C33 C34 C35 134.89(16) . . ? C44 C34 C35 108.16(15) . . ? C36 C35 C46 118.41(18) . . ? C36 C35 C34 135.99(18) . . ? C46 C35 C34 105.59(15) . . ? C35 C36 C37 118.40(19) . . ? C35 C36 H36 120.8 . . ? C37 C36 H36 120.8 . . ? C38 C37 C36 123.15(19) . . ? C38 C37 H37 118.4 . . ? C36 C37 H37 118.4 . . ? C37 C38 C39 119.42(18) . . ? C37 C38 H38 120.3 . . ? C39 C38 H38 120.3 . . ? C46 C39 C40 116.84(17) . . ? C46 C39 C38 116.83(18) . . ? C40 C39 C38 126.32(18) . . ? C41 C40 C39 119.52(18) . . ? C41 C40 H40 120.2 . . ? C39 C40 H40 120.2 . . ? C40 C41 C42 123.10(19) . . ? C40 C41 H41 118.5 . . ? C42 C41 H41 118.5 . . ? C43 C42 C41 118.47(19) . . ? C43 C42 H42 120.8 . . ? C41 C42 H42 120.8 . . ? C42 C43 C46 118.15(17) . . ? C42 C43 C44 135.96(18) . . ? C46 C43 C44 105.89(15) . . ? C45 C44 C34 116.65(17) . . ? C45 C44 C43 135.30(17) . . ? C34 C44 C43 108.05(16) . . ? N31 C45 C44 122.35(17) . . ? N31 C45 C50 112.88(15) . . ? C44 C45 C50 124.78(16) . . ? C39 C46 C43 123.92(17) . . ? C39 C46 C35 123.77(17) . . ? C43 C46 C35 112.31(16) . . ? O47 C47 O48 124.39(17) . . ? O47 C47 C33 124.90(18) . . ? O48 C47 C33 110.71(16) . . ? O48 C49 H491 109.5 . . ? O48 C49 H492 109.5 . . ? H491 C49 H492 109.5 . . ? O48 C49 H493 109.5 . . ? H491 C49 H493 109.5 . . ? H492 C49 H493 109.5 . . ? O50 C50 O51 123.19(18) . . ? O50 C50 C45 125.16(18) . . ? O51 C50 C45 111.65(16) . . ? O51 C52 H521 109.5 . . ? O51 C52 H522 109.5 . . ? H521 C52 H522 109.5 . . ? O51 C52 H523 109.5 . . ? H521 C52 H523 109.5 . . ? H522 C52 H523 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N1 N2 C3 -0.7(3) . . . . ? N1 N2 C3 C4 -1.9(4) . . . . ? N1 N2 C3 C17 177.1(2) . . . . ? N2 C3 C4 C14 2.4(3) . . . . ? C17 C3 C4 C14 -176.6(2) . . . . ? N2 C3 C4 C5 -176.0(3) . . . . ? C17 C3 C4 C5 5.1(4) . . . . ? C3 C4 C5 C6 -1.3(5) . . . . ? C14 C4 C5 C6 -179.7(2) . . . . ? C3 C4 C5 C16 178.9(3) . . . . ? C14 C4 C5 C16 0.5(2) . . . . ? C16 C5 C6 C7 -0.4(3) . . . . ? C4 C5 C6 C7 179.9(3) . . . . ? C5 C6 C7 C8 0.1(4) . . . . ? C6 C7 C8 C9 0.3(4) . . . . ? C7 C8 C9 C16 -0.5(3) . . . . ? C7 C8 C9 C10 178.5(3) . . . . ? C16 C9 C10 C11 -0.4(4) . . . . ? C8 C9 C10 C11 -179.4(3) . . . . ? C9 C10 C11 C12 -0.5(4) . . . . ? C10 C11 C12 C13 0.4(4) . . . . ? C11 C12 C13 C16 0.5(4) . . . . ? C11 C12 C13 C14 179.1(3) . . . . ? C3 C4 C14 C15 -0.3(3) . . . . ? C5 C4 C14 C15 178.4(2) . . . . ? C3 C4 C14 C13 -179.4(2) . . . . ? C5 C4 C14 C13 -0.7(3) . . . . ? C12 C13 C14 C15 3.0(5) . . . . ? C16 C13 C14 C15 -178.3(3) . . . . ? C12 C13 C14 C4 -178.2(3) . . . . ? C16 C13 C14 C4 0.5(2) . . . . ? N2 N1 C15 C14 2.8(4) . . . . ? N2 N1 C15 C20 -177.1(2) . . . . ? C4 C14 C15 N1 -2.2(3) . . . . ? C13 C14 C15 N1 176.6(2) . . . . ? C4 C14 C15 C20 177.7(2) . . . . ? C13 C14 C15 C20 -3.5(4) . . . . ? C10 C9 C16 C5 -178.9(2) . . . . ? C8 C9 C16 C5 0.2(3) . . . . ? C10 C9 C16 C13 1.4(3) . . . . ? C8 C9 C16 C13 -179.6(2) . . . . ? C6 C5 C16 C9 0.2(3) . . . . ? C4 C5 C16 C9 -180.0(2) . . . . ? C6 C5 C16 C13 -180.0(2) . . . . ? C4 C5 C16 C13 -0.2(3) . . . . ? C12 C13 C16 C9 -1.4(3) . . . . ? C14 C13 C16 C9 179.6(2) . . . . ? C12 C13 C16 C5 178.8(2) . . . . ? C14 C13 C16 C5 -0.2(3) . . . . ? C19 O18 C17 O17 -0.6(4) . . . . ? C19 O18 C17 C3 -178.6(2) . . . . ? N2 C3 C17 O17 -161.6(2) . . . . ? C4 C3 C17 O17 17.4(4) . . . . ? N2 C3 C17 O18 16.4(3) . . . . ? C4 C3 C17 O18 -164.6(2) . . . . ? C22 O21 C20 O20 -0.5(4) . . . . ? C22 O21 C20 C15 179.0(2) . . . . ? N1 C15 C20 O20 -178.7(3) . . . . ? C14 C15 C20 O20 1.4(4) . . . . ? N1 C15 C20 O21 1.7(3) . . . . ? C14 C15 C20 O21 -178.2(2) . . . . ? C45 N31 N32 C33 -0.7(4) . . . . ? N31 N32 C33 C34 0.0(4) . . . . ? N31 N32 C33 C47 -179.6(2) . . . . ? N32 C33 C34 C44 0.8(3) . . . . ? C47 C33 C34 C44 -179.7(2) . . . . ? N32 C33 C34 C35 179.5(3) . . . . ? C47 C33 C34 C35 -0.9(4) . . . . ? C33 C34 C35 C36 2.4(5) . . . . ? C44 C34 C35 C36 -178.8(3) . . . . ? C33 C34 C35 C46 -179.0(3) . . . . ? C44 C34 C35 C46 -0.1(3) . . . . ? C46 C35 C36 C37 1.4(3) . . . . ? C34 C35 C36 C37 179.9(3) . . . . ? C35 C36 C37 C38 -1.0(4) . . . . ? C36 C37 C38 C39 -0.1(4) . . . . ? C37 C38 C39 C46 0.8(3) . . . . ? C37 C38 C39 C40 -178.5(3) . . . . ? C46 C39 C40 C41 0.0(4) . . . . ? C38 C39 C40 C41 179.4(3) . . . . ? C39 C40 C41 C42 0.3(4) . . . . ? C40 C41 C42 C43 -0.3(5) . . . . ? C41 C42 C43 C46 0.0(4) . . . . ? C41 C42 C43 C44 -179.4(3) . . . . ? C33 C34 C44 C45 -0.9(3) . . . . ? C35 C34 C44 C45 -179.9(2) . . . . ? C33 C34 C44 C43 179.5(2) . . . . ? C35 C34 C44 C43 0.4(3) . . . . ? C42 C43 C44 C45 -0.7(5) . . . . ? C46 C43 C44 C45 179.9(3) . . . . ? C42 C43 C44 C34 178.9(3) . . . . ? C46 C43 C44 C34 -0.5(3) . . . . ? N32 N31 C45 C44 0.6(4) . . . . ? N32 N31 C45 C50 -179.5(2) . . . . ? C34 C44 C45 N31 0.2(3) . . . . ? C43 C44 C45 N31 179.8(3) . . . . ? C34 C44 C45 C50 -179.7(2) . . . . ? C43 C44 C45 C50 -0.1(4) . . . . ? C40 C39 C46 C43 -0.4(4) . . . . ? C38 C39 C46 C43 -179.8(2) . . . . ? C40 C39 C46 C35 179.0(2) . . . . ? C38 C39 C46 C35 -0.4(4) . . . . ? C42 C43 C46 C39 0.4(4) . . . . ? C44 C43 C46 C39 179.9(2) . . . . ? C42 C43 C46 C35 -179.1(2) . . . . ? C44 C43 C46 C35 0.4(3) . . . . ? C36 C35 C46 C39 -0.7(4) . . . . ? C34 C35 C46 C39 -179.7(2) . . . . ? C36 C35 C46 C43 178.7(2) . . . . ? C34 C35 C46 C43 -0.2(3) . . . . ? C49 O48 C47 O47 -1.4(3) . . . . ? C49 O48 C47 C33 177.8(2) . . . . ? N32 C33 C47 O47 163.0(2) . . . . ? C34 C33 C47 O47 -16.6(4) . . . . ? N32 C33 C47 O48 -16.1(3) . . . . ? C34 C33 C47 O48 164.3(2) . . . . ? C52 O51 C50 O50 1.6(4) . . . . ? C52 O51 C50 C45 -178.9(2) . . . . ? N31 C45 C50 O50 176.8(3) . . . . ? C44 C45 C50 O50 -3.3(4) . . . . ? N31 C45 C50 O51 -2.7(3) . . . . ? C44 C45 C50 O51 177.2(2) . . . . ? # End of CIF ============================================================ # Attachment '3,8-dibromoacenapthylene_compound3.cif' data_SG0630 _database_code_depnum_ccdc_archive 'CCDC 713714' _audit_creation_method SHELXL-97 _audit_creation_date 06-09-07 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C12 H6 Br2' _chemical_formula_sum 'C12 H6 Br2' _chemical_formula_weight 309.99 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 48 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 24 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; Br Br 8 -0.2901 2.4595 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.8327(2) _cell_length_b 19.1058(4) _cell_length_c 6.8699(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.7697(13) _cell_angle_gamma 90.00 _cell_volume 989.39(4) _cell_formula_units_Z 4 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 11983 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description tablet _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.081 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 8.167 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_absorpt_correction_T_min 0.189 _exptl_absorpt_correction_T_max 0.394 _exptl_special_details ; Solvent used: dichloromethane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.438(1) Frames collected: 324 Seconds exposure per frame: 14 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.8 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 22044 _diffrn_reflns_av_R_equivalents 0.0840 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 30.03 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 1.000 _reflns_number_total 2893 _reflns_number_gt 2315 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0567P)^2^+0.3292P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0182(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2893 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1004 _refine_ls_wR_factor_gt 0.0937 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.887 _refine_diff_density_min -0.760 _refine_diff_density_rms 0.190 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.23894(5) 0.498298(15) 0.31780(6) 0.03529(13) Uani 1 1 d . . . Br2 Br 0.44219(4) 0.907248(15) 0.38477(5) 0.02987(13) Uani 1 1 d . . . C1 C 0.4957(4) 0.72605(15) 0.3979(4) 0.0224(6) Uani 1 1 d . . . H1 H 0.6105 0.7464 0.4268 0.027 Uiso 1 1 calc R . . C2 C 0.4597(4) 0.65638(15) 0.3864(4) 0.0226(6) Uani 1 1 d . . . H2 H 0.5453 0.6200 0.4058 0.027 Uiso 1 1 calc R . . C3 C 0.2667(4) 0.64643(14) 0.3392(4) 0.0195(5) Uani 1 1 d . . . C4 C 0.1516(4) 0.59088(13) 0.3054(4) 0.0220(5) Uani 1 1 d . . . C5 C -0.0342(4) 0.60224(15) 0.2586(4) 0.0247(6) Uani 1 1 d . . . H5 H -0.1123 0.5632 0.2361 0.030 Uiso 1 1 calc R . . C6 C -0.1029(4) 0.66875(16) 0.2452(4) 0.0239(6) Uani 1 1 d . . . H6 H -0.2277 0.6752 0.2132 0.029 Uiso 1 1 calc R . . C7 C 0.0112(4) 0.72791(15) 0.2788(4) 0.0207(5) Uani 1 1 d . . . C8 C -0.0365(4) 0.80041(15) 0.2687(4) 0.0248(6) Uani 1 1 d . . . H8 H -0.1578 0.8136 0.2390 0.030 Uiso 1 1 calc R . . C9 C 0.0921(4) 0.85072(15) 0.3017(4) 0.0256(6) Uani 1 1 d . . . H9 H 0.0583 0.8986 0.2942 0.031 Uiso 1 1 calc R . . C10 C 0.2750(4) 0.83337(15) 0.3470(4) 0.0222(6) Uani 1 1 d . . . C11 C 0.3278(4) 0.76470(14) 0.3583(4) 0.0188(5) Uani 1 1 d . . . C12 C 0.1907(4) 0.71408(14) 0.3233(4) 0.0188(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0359(2) 0.01568(17) 0.0537(2) -0.00059(12) 0.01103(16) -0.00078(11) Br2 0.0394(2) 0.01899(17) 0.03155(19) -0.00108(11) 0.01015(13) -0.00754(11) C1 0.0204(13) 0.0228(13) 0.0241(13) -0.0014(11) 0.0060(10) -0.0013(11) C2 0.0218(14) 0.0224(13) 0.0233(13) 0.0006(10) 0.0055(10) 0.0021(10) C3 0.0241(14) 0.0163(12) 0.0182(12) -0.0004(9) 0.0060(10) 0.0004(10) C4 0.0262(15) 0.0154(12) 0.0249(13) 0.0007(10) 0.0077(11) 0.0004(10) C5 0.0233(14) 0.0269(14) 0.0236(13) -0.0003(11) 0.0058(11) -0.0063(11) C6 0.0181(13) 0.0300(15) 0.0244(13) -0.0004(11) 0.0071(10) -0.0003(11) C7 0.0241(14) 0.0217(12) 0.0172(12) 0.0007(10) 0.0073(10) 0.0000(10) C8 0.0254(15) 0.0249(14) 0.0245(14) 0.0027(11) 0.0075(11) 0.0064(11) C9 0.0348(16) 0.0205(13) 0.0220(13) 0.0025(10) 0.0086(11) 0.0057(12) C10 0.0309(15) 0.0184(12) 0.0177(12) -0.0006(9) 0.0074(10) -0.0043(11) C11 0.0199(13) 0.0184(12) 0.0183(12) -0.0002(9) 0.0055(10) -0.0008(10) C12 0.0221(13) 0.0177(12) 0.0166(12) 0.0004(9) 0.0055(10) -0.0005(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C4 1.890(3) . ? Br2 C10 1.894(3) . ? C1 C2 1.358(4) . ? C1 C11 1.467(4) . ? C1 H1 0.9500 . ? C2 C3 1.470(4) . ? C2 H2 0.9500 . ? C3 C4 1.371(4) . ? C3 C12 1.415(4) . ? C4 C5 1.419(4) . ? C5 C6 1.373(4) . ? C5 H5 0.9500 . ? C6 C7 1.420(4) . ? C6 H6 0.9500 . ? C7 C12 1.380(4) . ? C7 C8 1.431(4) . ? C8 C9 1.366(4) . ? C8 H8 0.9500 . ? C9 C10 1.420(4) . ? C9 H9 0.9500 . ? C10 C11 1.372(4) . ? C11 C12 1.417(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C11 108.7(3) . . ? C2 C1 H1 125.6 . . ? C11 C1 H1 125.6 . . ? C1 C2 C3 108.9(3) . . ? C1 C2 H2 125.5 . . ? C3 C2 H2 125.5 . . ? C4 C3 C12 116.8(3) . . ? C4 C3 C2 136.7(3) . . ? C12 C3 C2 106.6(2) . . ? C3 C4 C5 120.5(3) . . ? C3 C4 Br1 120.2(2) . . ? C5 C4 Br1 119.3(2) . . ? C6 C5 C4 121.0(3) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 120.5(3) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C12 C7 C6 116.2(3) . . ? C12 C7 C8 115.6(3) . . ? C6 C7 C8 128.2(3) . . ? C9 C8 C7 120.1(3) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 121.8(3) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C11 C10 C9 120.4(3) . . ? C11 C10 Br2 121.2(2) . . ? C9 C10 Br2 118.3(2) . . ? C10 C11 C12 116.1(3) . . ? C10 C11 C1 137.2(3) . . ? C12 C11 C1 106.7(2) . . ? C7 C12 C3 125.0(3) . . ? C7 C12 C11 125.9(2) . . ? C3 C12 C11 109.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C1 C2 C3 -0.1(3) . . . . ? C1 C2 C3 C4 178.5(3) . . . . ? C1 C2 C3 C12 0.0(3) . . . . ? C12 C3 C4 C5 -0.4(4) . . . . ? C2 C3 C4 C5 -178.8(3) . . . . ? C12 C3 C4 Br1 178.81(19) . . . . ? C2 C3 C4 Br1 0.4(5) . . . . ? C3 C4 C5 C6 0.2(4) . . . . ? Br1 C4 C5 C6 -179.0(2) . . . . ? C4 C5 C6 C7 -0.2(4) . . . . ? C5 C6 C7 C12 0.4(4) . . . . ? C5 C6 C7 C8 179.1(3) . . . . ? C12 C7 C8 C9 0.1(4) . . . . ? C6 C7 C8 C9 -178.6(3) . . . . ? C7 C8 C9 C10 -0.2(4) . . . . ? C8 C9 C10 C11 0.2(4) . . . . ? C8 C9 C10 Br2 178.7(2) . . . . ? C9 C10 C11 C12 -0.2(4) . . . . ? Br2 C10 C11 C12 -178.73(18) . . . . ? C9 C10 C11 C1 179.5(3) . . . . ? Br2 C10 C11 C1 1.0(5) . . . . ? C2 C1 C11 C10 -179.6(3) . . . . ? C2 C1 C11 C12 0.2(3) . . . . ? C6 C7 C12 C3 -0.6(4) . . . . ? C8 C7 C12 C3 -179.5(3) . . . . ? C6 C7 C12 C11 178.7(2) . . . . ? C8 C7 C12 C11 -0.2(4) . . . . ? C4 C3 C12 C7 0.6(4) . . . . ? C2 C3 C12 C7 179.5(2) . . . . ? C4 C3 C12 C11 -178.8(2) . . . . ? C2 C3 C12 C11 0.1(3) . . . . ? C10 C11 C12 C7 0.2(4) . . . . ? C1 C11 C12 C7 -179.6(2) . . . . ? C10 C11 C12 C3 179.7(2) . . . . ? C1 C11 C12 C3 -0.1(3) . . . . ? # Attachment '7,10-di(furan-2-yl)-1,6-dimethyl-8,9-diazafluoranthene.cif' data_SG0806 _database_code_depnum_ccdc_archive 'CCDC 713715' _audit_creation_method SHELXL-97 _audit_creation_date 08-04-29 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C24 H16 N2 O2' _chemical_formula_sum 'C24 H16 N2 O2' _chemical_formula_weight 364.40 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 96 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 64 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 8 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 8 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.3569(5) _cell_length_b 9.9526(6) _cell_length_c 21.8278(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.864(4) _cell_angle_gamma 90.00 _cell_volume 1782.94(17) _cell_formula_units_Z 4 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 3208 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.0875 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: acetone Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 1.143(2) Frames collected: 929 Seconds exposure per frame: 12 Degrees rotation per frame: 0.5 Crystal-Detector distance (mm): 32.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 21964 _diffrn_reflns_av_R_equivalents 0.0950 _diffrn_reflns_av_sigmaI/netI 0.0690 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 24.96 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.993 _reflns_number_total 3189 _reflns_number_gt 1544 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _refine_special_details ; The crystals are twinned by a two-fold rotation about [201]. The twin volume fraction of the major twin component is 0.247(2). There is some suggestion that the structure should belong to a higher symmetry space group (C2/c), however, attempts to refine the structure in this higher symmetry space group gave inferior results and many systematic absence violations. The current model refuses to converge with the displacement parameters of the two central C atoms, C(4) and C(14), "hunting" around some mean value. It is thought that this is a consequence of matrix correlations brought about by the pseudo-symmetry. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0745P)^2^+0.3825P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3189 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1263 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_ref 0.1775 _refine_ls_wR_factor_gt 0.1336 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 1.336 _refine_ls_shift/su_mean 0.221 _refine_diff_density_max 0.176 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.039 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8680(5) 0.2692(4) 0.16932(16) 0.0696(14) Uani 1 1 d . . . O2 O 0.6310(5) 0.2720(4) -0.16810(17) 0.0718(14) Uani 1 1 d . . . N1 N 0.7076(8) 0.4207(5) -0.0291(2) 0.0712(18) Uani 1 1 d . . . N2 N 0.7906(8) 0.4213(5) 0.0290(2) 0.0694(17) Uani 1 1 d . . . C3 C 0.8418(7) 0.3047(5) 0.0578(3) 0.0511(16) Uani 1 1 d . . . C4 C 0.8047(7) 0.1807(6) 0.0292(2) 0.0421(15) Uani 1 1 d . . . C5 C 0.8493(7) 0.0413(6) 0.0465(3) 0.0385(15) Uani 1 1 d . . . C6 C 0.9615(8) -0.0243(5) 0.0922(3) 0.0406(15) Uani 1 1 d . . . C7 C 0.9628(7) -0.1693(5) 0.0908(2) 0.0458(15) Uani 1 1 d . . . H7 H 1.0383 -0.2159 0.1215 0.055 Uiso 1 1 calc R . . C8 C 0.8602(7) -0.2418(6) 0.0473(2) 0.0502(17) Uani 1 1 d . . . H8 H 0.8642 -0.3371 0.0491 0.060 Uiso 1 1 calc R . . C9 C 0.7484(9) -0.1792(2) -0.0004(3) 0.0421(7) Uani 1 1 d . . . C10 C 0.6377(7) -0.2439(6) -0.0477(2) 0.0485(16) Uani 1 1 d . . . H10 H 0.6323 -0.3392 -0.0500 0.058 Uiso 1 1 calc R . . C11 C 0.5378(7) -0.1659(5) -0.0903(2) 0.0494(16) Uani 1 1 d . . . H11 H 0.4637 -0.2107 -0.1221 0.059 Uiso 1 1 calc R . . C12 C 0.5362(9) -0.0238(5) -0.0908(3) 0.0448(17) Uani 1 1 d . . . C13 C 0.6491(8) 0.0388(6) -0.0459(3) 0.0407(15) Uani 1 1 d . . . C14 C 0.6935(7) 0.1802(6) -0.0290(2) 0.0414(15) Uani 1 1 d . . . C15 C 0.6573(7) 0.3056(5) -0.0581(2) 0.0504(17) Uani 1 1 d . . . C16 C 0.7488(10) -0.0391(3) -0.0007(3) 0.0402(7) Uani 1 1 d . . . C17 C 0.9306(8) 0.3278(6) 0.1224(3) 0.0605(18) Uani 1 1 d . . . C18 C 1.0590(9) 0.4071(6) 0.1446(3) 0.086(3) Uani 1 1 d . . . H18 H 1.1219 0.4596 0.1216 0.103 Uiso 1 1 calc R . . C19 C 1.0789(9) 0.3939(8) 0.2114(3) 0.103(3) Uani 1 1 d . . . H19 H 1.1600 0.4364 0.2415 0.123 Uiso 1 1 calc R . . C20 C 0.9616(10) 0.3105(9) 0.2232(3) 0.104(3) Uani 1 1 d . . . H20 H 0.9469 0.2845 0.2637 0.125 Uiso 1 1 calc R . . C21 C 1.0850(7) 0.0420(5) 0.1407(2) 0.0474(16) Uani 1 1 d . . . H211 H 1.1211 0.1257 0.1240 0.071 Uiso 1 1 calc R . . H212 H 1.1785 -0.0181 0.1528 0.071 Uiso 1 1 calc R . . H213 H 1.0368 0.0619 0.1772 0.071 Uiso 1 1 calc R . . C22 C 0.5696(8) 0.3304(6) -0.1202(3) 0.0570(18) Uani 1 1 d . . . C23 C 0.4400(9) 0.4070(7) -0.1446(3) 0.081(2) Uani 1 1 d . . . H23 H 0.3772 0.4598 -0.1216 0.097 Uiso 1 1 calc R . . C24 C 0.4138(10) 0.3954(8) -0.2098(3) 0.112(3) Uani 1 1 d . . . H24 H 0.3291 0.4365 -0.2389 0.134 Uiso 1 1 calc R . . C25 C 0.5324(9) 0.3145(8) -0.2230(3) 0.093(3) Uani 1 1 d . . . H25 H 0.5462 0.2903 -0.2638 0.111 Uiso 1 1 calc R . . C26 C 0.4139(7) 0.0430(6) -0.1413(2) 0.0559(17) Uani 1 1 d . . . H261 H 0.3733 0.1252 -0.1247 0.084 Uiso 1 1 calc R . . H262 H 0.3228 -0.0184 -0.1553 0.084 Uiso 1 1 calc R . . H263 H 0.4663 0.0657 -0.1765 0.084 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.078(3) 0.081(3) 0.047(2) -0.009(2) 0.004(2) 0.000(3) O2 0.081(4) 0.073(3) 0.059(3) 0.023(2) 0.006(2) -0.002(3) N1 0.102(5) 0.039(3) 0.064(4) -0.002(3) -0.007(3) 0.000(3) N2 0.099(5) 0.026(3) 0.076(4) -0.006(3) -0.002(3) -0.003(3) C3 0.060(4) 0.029(3) 0.064(4) -0.007(3) 0.009(3) -0.003(3) C4 0.052(4) 0.029(3) 0.046(3) -0.004(3) 0.013(3) -0.004(3) C5 0.041(4) 0.036(3) 0.039(3) -0.001(3) 0.007(3) -0.003(3) C6 0.041(4) 0.040(3) 0.042(3) 0.008(3) 0.009(3) 0.001(3) C7 0.057(4) 0.034(3) 0.046(3) 0.010(3) 0.010(3) 0.008(3) C8 0.066(5) 0.031(3) 0.054(3) 0.001(3) 0.014(3) 0.001(3) C9 0.0511(19) 0.0291(15) 0.0465(16) 0.001(4) 0.0102(14) -0.004(5) C10 0.057(4) 0.030(3) 0.057(3) -0.004(3) 0.008(3) -0.002(3) C11 0.057(4) 0.041(3) 0.048(3) -0.006(3) 0.006(3) -0.007(3) C12 0.057(4) 0.040(3) 0.036(3) 0.004(3) 0.005(3) 0.000(3) C13 0.054(4) 0.027(3) 0.041(3) 0.000(3) 0.010(3) -0.002(3) C14 0.046(4) 0.031(3) 0.046(3) 0.000(3) 0.007(3) -0.002(3) C15 0.067(4) 0.028(3) 0.053(4) 0.002(3) 0.004(3) 0.003(3) C16 0.0447(18) 0.0318(15) 0.0438(16) -0.006(4) 0.0076(14) -0.005(4) C17 0.078(5) 0.042(3) 0.058(4) -0.013(3) 0.003(4) 0.003(4) C18 0.094(6) 0.055(4) 0.094(6) -0.020(4) -0.018(5) -0.014(5) C19 0.102(7) 0.088(5) 0.096(6) -0.046(5) -0.037(5) 0.003(5) C20 0.121(8) 0.124(7) 0.064(5) -0.044(5) 0.006(5) -0.012(7) C21 0.050(4) 0.044(3) 0.044(3) 0.001(3) -0.001(3) 0.003(4) C22 0.076(5) 0.034(3) 0.058(4) 0.009(3) 0.005(4) 0.000(4) C23 0.085(6) 0.058(4) 0.090(5) 0.015(4) -0.007(4) 0.016(5) C24 0.109(8) 0.111(7) 0.103(6) 0.043(6) -0.014(5) 0.013(6) C25 0.106(7) 0.101(6) 0.058(4) 0.030(5) -0.016(4) -0.029(6) C26 0.060(5) 0.057(3) 0.051(4) 0.003(4) 0.009(3) 0.002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C20 1.348(6) . ? O1 C17 1.366(7) . ? O2 C22 1.378(7) . ? O2 C25 1.386(6) . ? N1 N2 1.326(4) . ? N1 C15 1.338(7) . ? N2 C3 1.350(7) . ? C3 C4 1.392(7) . ? C3 C17 1.483(7) . ? C4 C14 1.426(4) . ? C4 C5 1.467(8) . ? C5 C6 1.395(8) . ? C5 C16 1.443(8) . ? C6 C7 1.444(7) . ? C6 C21 1.485(8) . ? C7 C8 1.361(7) . ? C7 H7 0.9500 . ? C8 C9 1.405(7) . ? C8 H8 0.9500 . ? C9 C16 1.395(4) . ? C9 C10 1.407(7) . ? C10 C11 1.368(7) . ? C10 H10 0.9500 . ? C11 C12 1.415(7) . ? C11 H11 0.9500 . ? C12 C13 1.376(8) . ? C12 C26 1.508(8) . ? C13 C16 1.399(9) . ? C13 C14 1.484(8) . ? C14 C15 1.406(7) . ? C15 C22 1.435(7) . ? C17 C18 1.346(8) . ? C18 C19 1.442(9) . ? C18 H18 0.9500 . ? C19 C20 1.347(10) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H211 0.9800 . ? C21 H212 0.9800 . ? C21 H213 0.9800 . ? C22 C23 1.350(8) . ? C23 C24 1.404(9) . ? C23 H23 0.9500 . ? C24 C25 1.350(10) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 H261 0.9800 . ? C26 H262 0.9800 . ? C26 H263 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C20 O1 C17 106.4(6) . . ? C22 O2 C25 106.4(6) . . ? N2 N1 C15 121.2(6) . . ? N1 N2 C3 120.2(6) . . ? N2 C3 C4 122.0(5) . . ? N2 C3 C17 111.5(5) . . ? C4 C3 C17 126.4(5) . . ? C3 C4 C14 117.1(7) . . ? C3 C4 C5 134.3(5) . . ? C14 C4 C5 108.5(6) . . ? C6 C5 C16 118.3(5) . . ? C6 C5 C4 136.9(5) . . ? C16 C5 C4 104.7(5) . . ? C5 C6 C7 117.3(5) . . ? C5 C6 C21 125.8(5) . . ? C7 C6 C21 116.8(5) . . ? C8 C7 C6 122.6(5) . . ? C8 C7 H7 118.7 . . ? C6 C7 H7 118.7 . . ? C7 C8 C9 121.7(5) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.1 . . ? C16 C9 C8 116.4(6) . . ? C16 C9 C10 117.1(6) . . ? C8 C9 C10 126.5(2) . . ? C11 C10 C9 118.2(5) . . ? C11 C10 H10 120.9 . . ? C9 C10 H10 121.0 . . ? C10 C11 C12 125.2(5) . . ? C10 C11 H11 117.4 . . ? C12 C11 H11 117.4 . . ? C13 C12 C11 116.3(6) . . ? C13 C12 C26 126.9(5) . . ? C11 C12 C26 116.8(5) . . ? C12 C13 C16 119.3(5) . . ? C12 C13 C14 135.4(5) . . ? C16 C13 C14 105.2(5) . . ? C15 C14 C4 116.6(6) . . ? C15 C14 C13 135.0(5) . . ? C4 C14 C13 108.3(6) . . ? N1 C15 C14 121.6(5) . . ? N1 C15 C22 111.0(5) . . ? C14 C15 C22 127.4(5) . . ? C9 C16 C13 123.8(6) . . ? C9 C16 C5 123.5(6) . . ? C13 C16 C5 112.7(2) . . ? C18 C17 O1 111.8(6) . . ? C18 C17 C3 131.0(7) . . ? O1 C17 C3 117.0(6) . . ? C17 C18 C19 104.1(7) . . ? C17 C18 H18 128.1 . . ? C19 C18 H18 127.8 . . ? C20 C19 C18 107.5(6) . . ? C20 C19 H19 126.2 . . ? C18 C19 H19 126.3 . . ? C19 C20 O1 110.1(7) . . ? C19 C20 H20 125.0 . . ? O1 C20 H20 124.9 . . ? C6 C21 H211 109.5 . . ? C6 C21 H212 109.4 . . ? H211 C21 H212 109.5 . . ? C6 C21 H213 109.5 . . ? H211 C21 H213 109.5 . . ? H212 C21 H213 109.5 . . ? C23 C22 O2 108.9(6) . . ? C23 C22 C15 134.4(7) . . ? O2 C22 C15 116.6(6) . . ? C22 C23 C24 108.3(7) . . ? C22 C23 H23 125.7 . . ? C24 C23 H23 126.0 . . ? C25 C24 C23 106.6(7) . . ? C25 C24 H24 126.7 . . ? C23 C24 H24 126.7 . . ? C24 C25 O2 109.7(7) . . ? C24 C25 H25 125.1 . . ? O2 C25 H25 125.2 . . ? C12 C26 H261 109.5 . . ? C12 C26 H262 109.5 . . ? H261 C26 H262 109.5 . . ? C12 C26 H263 109.4 . . ? H261 C26 H263 109.5 . . ? H262 C26 H263 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N1 N2 C3 7.4(5) . . . . ? N1 N2 C3 C4 -2.7(8) . . . . ? N1 N2 C3 C17 -179.5(4) . . . . ? N2 C3 C4 C14 -7.4(8) . . . . ? C17 C3 C4 C14 169.0(5) . . . . ? N2 C3 C4 C5 175.9(8) . . . . ? C17 C3 C4 C5 -7.8(11) . . . . ? C3 C4 C5 C6 -11.7(13) . . . . ? C14 C4 C5 C6 171.4(7) . . . . ? C3 C4 C5 C16 171.9(7) . . . . ? C14 C4 C5 C16 -5.1(6) . . . . ? C16 C5 C6 C7 -3.2(10) . . . . ? C4 C5 C6 C7 -179.4(7) . . . . ? C16 C5 C6 C21 174.0(6) . . . . ? C4 C5 C6 C21 -2.2(13) . . . . ? C5 C6 C7 C8 0.0(10) . . . . ? C21 C6 C7 C8 -177.5(6) . . . . ? C6 C7 C8 C9 1.6(10) . . . . ? C7 C8 C9 C16 0.2(11) . . . . ? C7 C8 C9 C10 179.7(5) . . . . ? C16 C9 C10 C11 -0.4(11) . . . . ? C8 C9 C10 C11 -179.9(5) . . . . ? C9 C10 C11 C12 -0.1(10) . . . . ? C10 C11 C12 C13 2.6(11) . . . . ? C10 C11 C12 C26 -178.8(6) . . . . ? C11 C12 C13 C16 -4.4(11) . . . . ? C26 C12 C13 C16 177.2(7) . . . . ? C11 C12 C13 C14 179.1(8) . . . . ? C26 C12 C13 C14 0.7(14) . . . . ? C3 C4 C14 C15 12.4(4) . . . . ? C5 C4 C14 C15 -170.1(6) . . . . ? C3 C4 C14 C13 -170.4(6) . . . . ? C5 C4 C14 C13 7.1(3) . . . . ? C12 C13 C14 C15 -13.0(14) . . . . ? C16 C13 C14 C15 170.2(7) . . . . ? C12 C13 C14 C4 170.6(8) . . . . ? C16 C13 C14 C4 -6.3(6) . . . . ? N2 N1 C15 C14 -1.6(9) . . . . ? N2 N1 C15 C22 179.7(4) . . . . ? C4 C14 C15 N1 -8.4(8) . . . . ? C13 C14 C15 N1 175.4(8) . . . . ? C4 C14 C15 C22 170.1(5) . . . . ? C13 C14 C15 C22 -6.2(12) . . . . ? C8 C9 C16 C13 178.0(7) . . . . ? C10 C9 C16 C13 -1.6(13) . . . . ? C8 C9 C16 C5 -3.7(13) . . . . ? C10 C9 C16 C5 176.7(6) . . . . ? C12 C13 C16 C9 4.2(13) . . . . ? C14 C13 C16 C9 -178.4(9) . . . . ? C12 C13 C16 C5 -174.3(5) . . . . ? C14 C13 C16 C5 3.1(10) . . . . ? C6 C5 C16 C9 5.3(13) . . . . ? C4 C5 C16 C9 -177.4(8) . . . . ? C6 C5 C16 C13 -176.2(5) . . . . ? C4 C5 C16 C13 1.1(10) . . . . ? C20 O1 C17 C18 -1.2(8) . . . . ? C20 O1 C17 C3 -176.2(6) . . . . ? N2 C3 C17 C18 -53.7(10) . . . . ? C4 C3 C17 C18 129.6(8) . . . . ? N2 C3 C17 O1 120.2(6) . . . . ? C4 C3 C17 O1 -56.5(9) . . . . ? O1 C17 C18 C19 1.1(7) . . . . ? C3 C17 C18 C19 175.3(6) . . . . ? C17 C18 C19 C20 -0.7(8) . . . . ? C18 C19 C20 O1 0.0(10) . . . . ? C17 O1 C20 C19 0.7(9) . . . . ? C25 O2 C22 C23 -0.8(7) . . . . ? C25 O2 C22 C15 -177.3(5) . . . . ? N1 C15 C22 C23 -54.2(10) . . . . ? C14 C15 C22 C23 127.2(8) . . . . ? N1 C15 C22 O2 121.1(6) . . . . ? C14 C15 C22 O2 -57.4(9) . . . . ? O2 C22 C23 C24 1.6(8) . . . . ? C15 C22 C23 C24 177.2(7) . . . . ? C22 C23 C24 C25 -1.8(9) . . . . ? C23 C24 C25 O2 1.3(9) . . . . ? C22 O2 C25 C24 -0.4(8) . . . . ?