data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Shu Tu' _publ_contact_author_email LAOTU@XZNU.EDU.CN _publ_section_title ; A novel domino reaction for the selective synthesis of tetracyclic cinnolino[5,4,3-cde]cinnolines ; _publ_author_name 'Shujiang Tu.' # Attachment '2a.cif' data_041203d _database_code_depnum_ccdc_archive 'CCDC 695205' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 N4' _chemical_formula_weight 268.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 12.819(4) _cell_length_b 8.441(3) _cell_length_c 13.310(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.462(5) _cell_angle_gamma 90.00 _cell_volume 1433.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1230 _cell_measurement_theta_min 2.319 _cell_measurement_theta_max 23.229 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9751 _exptl_absorpt_correction_T_max 0.9841 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7218 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.1223 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2518 _reflns_number_gt 1416 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.3048P] 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 2518 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1079 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1785 _refine_ls_wR_factor_gt 0.1342 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 1.11488(18) 0.2369(3) 0.00759(19) 0.0510(7) Uani 1 1 d . . . N2 N 1.16426(18) 0.1239(3) -0.04672(19) 0.0513(7) Uani 1 1 d . . . N3 N 0.50653(19) 0.2577(3) -0.08920(17) 0.0469(6) Uani 1 1 d . . . N4 N 0.56253(19) 0.1517(3) -0.14224(17) 0.0470(6) Uani 1 1 d . . . C1 C 1.0250(2) 0.2044(3) 0.04438(19) 0.0394(7) Uani 1 1 d . . . C2 C 0.97626(18) 0.0553(3) 0.02796(18) 0.0350(7) Uani 1 1 d . . . C3 C 1.1205(2) -0.0146(3) -0.06568(19) 0.0408(7) Uani 1 1 d . . . C4 C 1.1709(2) -0.1336(3) -0.1275(2) 0.0522(8) Uani 1 1 d . . . H4A H 1.2463 -0.1185 -0.1187 0.063 Uiso 1 1 calc R . . H4B H 1.1479 -0.1161 -0.1982 0.063 Uiso 1 1 calc R . . C5 C 0.9742(2) 0.3236(4) 0.1053(2) 0.0483(8) Uani 1 1 d . . . H5A H 0.9906 0.4287 0.0819 0.058 Uiso 1 1 calc R . . H5B H 1.0030 0.3146 0.1752 0.058 Uiso 1 1 calc R . . C6 C 0.8543(2) 0.3047(3) 0.0998(2) 0.0456(7) Uani 1 1 d . . . C7 C 0.8054(2) 0.3422(4) -0.0065(2) 0.0602(9) Uani 1 1 d . . . H7A H 0.8324 0.2704 -0.0536 0.090 Uiso 1 1 calc R . . H7B H 0.8224 0.4490 -0.0237 0.090 Uiso 1 1 calc R . . H7C H 0.7307 0.3308 -0.0091 0.090 Uiso 1 1 calc R . . C8 C 0.8112(3) 0.4183(4) 0.1746(3) 0.0705(10) Uani 1 1 d . . . H8A H 0.7364 0.4078 0.1711 0.106 Uiso 1 1 calc R . . H8B H 0.8290 0.5251 0.1582 0.106 Uiso 1 1 calc R . . H8C H 0.8411 0.3935 0.2416 0.106 Uiso 1 1 calc R . . C9 C 0.4617(2) 0.2110(3) -0.00971(19) 0.0380(7) Uani 1 1 d . . . C10 C 0.47112(19) 0.0524(3) 0.02548(18) 0.0361(7) Uani 1 1 d . . . C11 C 0.5739(2) 0.0028(3) -0.11235(19) 0.0386(7) Uani 1 1 d . . . C12 C 0.6346(2) -0.1106(3) -0.1700(2) 0.0460(8) Uani 1 1 d . . . H12A H 0.7083 -0.1023 -0.1463 0.055 Uiso 1 1 calc R . . H12B H 0.6267 -0.0816 -0.2408 0.055 Uiso 1 1 calc R . . C13 C 0.3987(2) 0.3244(3) 0.0462(2) 0.0443(7) Uani 1 1 d . . . H13A H 0.3267 0.3235 0.0162 0.053 Uiso 1 1 calc R . . H13B H 0.4261 0.4306 0.0394 0.053 Uiso 1 1 calc R . . C14 C 0.4010(2) 0.2827(3) 0.1591(2) 0.0448(8) Uani 1 1 d . . . C15 C 0.5115(3) 0.3042(4) 0.2106(2) 0.0646(10) Uani 1 1 d . . . H15A H 0.5326 0.4127 0.2047 0.097 Uiso 1 1 calc R . . H15B H 0.5590 0.2368 0.1790 0.097 Uiso 1 1 calc R . . H15C H 0.5124 0.2767 0.2807 0.097 Uiso 1 1 calc R . . C16 C 0.3261(3) 0.3920(4) 0.2079(2) 0.0652(10) Uani 1 1 d . . . H16A H 0.3267 0.3663 0.2782 0.098 Uiso 1 1 calc R . . H16B H 0.2566 0.3788 0.1754 0.098 Uiso 1 1 calc R . . H16C H 0.3480 0.5000 0.2010 0.098 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 0.0418(15) 0.0440(15) 0.0675(17) -0.0044(13) 0.0070(13) -0.0085(12) N2 0.0442(14) 0.0409(15) 0.0702(17) -0.0011(13) 0.0122(12) -0.0060(12) N3 0.0583(16) 0.0392(14) 0.0445(14) 0.0062(11) 0.0117(12) -0.0001(12) N4 0.0593(16) 0.0392(15) 0.0442(14) 0.0036(11) 0.0133(12) -0.0027(12) C1 0.0385(16) 0.0370(17) 0.0416(16) 0.0016(13) -0.0025(13) -0.0029(13) C2 0.0322(15) 0.0314(15) 0.0402(16) 0.0033(11) -0.0026(12) -0.0019(11) C3 0.0413(16) 0.0387(17) 0.0424(16) 0.0057(13) 0.0045(13) -0.0017(14) C4 0.0490(18) 0.050(2) 0.0595(19) 0.0029(15) 0.0164(15) 0.0021(15) C5 0.0491(18) 0.0458(18) 0.0488(17) -0.0070(14) -0.0014(14) -0.0039(15) C6 0.0457(17) 0.0406(17) 0.0507(17) -0.0028(14) 0.0067(14) 0.0024(14) C7 0.055(2) 0.052(2) 0.071(2) 0.0042(17) -0.0062(16) 0.0062(16) C8 0.068(2) 0.061(2) 0.084(3) -0.0165(19) 0.0189(19) 0.0038(19) C9 0.0411(16) 0.0354(17) 0.0370(15) 0.0020(13) 0.0004(12) -0.0034(13) C10 0.0367(15) 0.0380(17) 0.0331(15) 0.0016(11) 0.0008(11) -0.0046(12) C11 0.0412(16) 0.0380(17) 0.0366(15) 0.0039(13) 0.0033(12) -0.0045(13) C12 0.0470(17) 0.0492(19) 0.0429(16) 0.0031(14) 0.0091(13) 0.0018(14) C13 0.0459(17) 0.0349(16) 0.0518(17) 0.0026(14) 0.0030(13) -0.0025(13) C14 0.0489(18) 0.0416(18) 0.0438(16) -0.0027(13) 0.0053(14) 0.0031(14) C15 0.064(2) 0.061(2) 0.065(2) -0.0108(18) -0.0099(17) -0.0014(18) C16 0.081(2) 0.060(2) 0.057(2) -0.0003(17) 0.0187(18) 0.0161(19) _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 C1 1.322(3) . ? N1 N2 1.386(3) . ? N2 C3 1.311(3) . ? N3 C9 1.312(3) . ? N3 N4 1.382(3) . ? N4 C11 1.323(4) . ? C1 C2 1.413(3) . ? C1 C5 1.482(4) . ? C2 C2 1.371(5) 3_755 ? C2 C3 1.423(3) 3_755 ? C3 C2 1.423(3) 3_755 ? C3 C4 1.485(4) . ? C4 C6 1.533(4) 3_755 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.540(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C8 1.524(4) . ? C6 C7 1.525(4) . ? C6 C4 1.533(4) 3_755 ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.420(4) . ? C9 C13 1.495(4) . ? C10 C10 1.373(5) 3_655 ? C10 C11 1.419(3) 3_655 ? C11 C10 1.419(3) 3_655 ? C11 C12 1.491(4) . ? C12 C14 1.534(4) 3_655 ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.541(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C16 1.521(4) . ? C14 C15 1.525(4) . ? C14 C12 1.534(4) 3_655 ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 C1 N1 N2 120.5(2) . . ? C3 N2 N1 120.4(2) . . ? C9 N3 N4 120.4(2) . . ? C11 N4 N3 120.6(2) . . ? N1 C1 C2 121.0(2) . . ? N1 C1 C5 120.4(2) . . ? C2 C1 C5 118.6(2) . . ? C2 C2 C1 118.5(3) 3_755 . ? C2 C2 C3 118.3(3) 3_755 3_755 ? C1 C2 C3 123.2(2) . 3_755 ? N2 C3 C2 121.2(2) . 3_755 ? N2 C3 C4 120.5(2) . . ? C2 C3 C4 118.2(2) 3_755 . ? C3 C4 C6 113.0(2) . 3_755 ? C3 C4 H4A 109.0 . . ? C6 C4 H4A 109.0 3_755 . ? C3 C4 H4B 109.0 . . ? C6 C4 H4B 109.0 3_755 . ? H4A C4 H4B 107.8 . . ? C1 C5 C6 113.1(2) . . ? C1 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? C1 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C8 C6 C7 109.5(3) . . ? C8 C6 C4 109.7(2) . 3_755 ? C7 C6 C4 110.0(2) . 3_755 ? C8 C6 C5 109.0(2) . . ? C7 C6 C5 110.1(2) . . ? C4 C6 C5 108.6(2) 3_755 . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 C10 121.3(2) . . ? N3 C9 C13 120.5(2) . . ? C10 C9 C13 118.2(2) . . ? C10 C10 C11 118.1(3) 3_655 3_655 ? C10 C10 C9 118.5(3) 3_655 . ? C11 C10 C9 123.4(2) 3_655 . ? N4 C11 C10 121.0(2) . 3_655 ? N4 C11 C12 120.2(2) . . ? C10 C11 C12 118.8(2) 3_655 . ? C11 C12 C14 112.6(2) . 3_655 ? C11 C12 H12A 109.1 . . ? C14 C12 H12A 109.1 3_655 . ? C11 C12 H12B 109.1 . . ? C14 C12 H12B 109.1 3_655 . ? H12A C12 H12B 107.8 . . ? C9 C13 C14 112.2(2) . . ? C9 C13 H13A 109.2 . . ? C14 C13 H13A 109.2 . . ? C9 C13 H13B 109.2 . . ? C14 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C16 C14 C15 109.4(3) . . ? C16 C14 C12 109.2(2) . 3_655 ? C15 C14 C12 110.0(2) . 3_655 ? C16 C14 C13 108.9(2) . . ? C15 C14 C13 110.0(2) . . ? C12 C14 C13 109.3(2) 3_655 . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.176 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.043 # Attachment '2b.cif' data_z0403 _database_code_depnum_ccdc_archive 'CCDC 695206' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2,3,6,7,8-hexahydro-cinnolino[5,4,3-cde]cinnoline ; _chemical_name_common ? _chemical_melting_point 543-544 _chemical_formula_moiety 'C12 H12 N4' _chemical_formula_sum 'C12 H12 N4' _chemical_formula_weight 212.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 9.698(5) _cell_length_b 5.875(3) _cell_length_c 10.023(5) _cell_angle_alpha 90.00 _cell_angle_beta 117.314(6) _cell_angle_gamma 90.00 _cell_volume 507.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 734 _cell_measurement_theta_min 2.364 _cell_measurement_theta_max 26.296 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9531 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2508 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.08 _diffrn_reflns_theta_max 25.03 _reflns_number_total 890 _reflns_number_gt 575 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 1998)' _computing_cell_refinement 'Bruker SMART (Bruker, 1999)' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1999)' _computing_publication_material 'Bruker SHELXTL' _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 'calc w=1/[\s^2^(Fo^2^)+(0.0655P)^2^+0.0552P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 890 _refine_ls_number_parameters 97 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.7159(2) -0.2597(3) 0.65617(19) 0.0547(6) Uani 1 1 d . . . N2 N 0.5861(2) -0.3398(3) 0.66438(18) 0.0555(6) Uani 1 1 d . . . C1 C 0.7050(2) -0.0820(4) 0.5729(2) 0.0466(6) Uani 1 1 d . . . C2 C 0.56377(19) 0.0384(3) 0.49395(18) 0.0390(5) Uani 1 1 d . . . C3 C 0.5474(2) 0.2352(3) 0.4062(2) 0.0450(5) Uani 1 1 d . . . C4 C 0.6864(3) 0.3211(5) 0.3949(3) 0.0581(7) Uani 1 1 d . . . C5 C 0.8354(3) 0.2567(4) 0.5326(3) 0.0647(7) Uani 1 1 d . . . C6 C 0.8445(3) 0.0004(4) 0.5597(3) 0.0621(7) Uani 1 1 d . . . H1 H 0.682(2) 0.250(4) 0.305(3) 0.065(6) Uiso 1 1 d . . . H2 H 0.678(2) 0.487(4) 0.382(2) 0.076(7) Uiso 1 1 d . . . H3 H 0.930(3) 0.308(4) 0.522(3) 0.086(8) Uiso 1 1 d . . . H4 H 0.839(3) 0.340(4) 0.623(3) 0.079(7) Uiso 1 1 d . . . H5 H 0.846(2) -0.086(4) 0.470(2) 0.072(7) Uiso 1 1 d . . . H6 H 0.936(3) -0.039(4) 0.649(3) 0.081(7) Uiso 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 N1 0.0567(12) 0.0508(12) 0.0500(10) 0.0061(8) 0.0187(9) 0.0164(9) N2 0.0652(12) 0.0458(11) 0.0474(11) 0.0086(8) 0.0189(9) 0.0115(9) C1 0.0501(12) 0.0467(12) 0.0395(10) -0.0019(10) 0.0175(9) 0.0102(10) C2 0.0445(11) 0.0386(11) 0.0306(9) -0.0029(8) 0.0146(8) 0.0072(8) C3 0.0574(13) 0.0386(12) 0.0351(10) -0.0010(9) 0.0178(9) 0.0051(10) C4 0.0737(17) 0.0505(15) 0.0555(14) -0.0027(12) 0.0344(13) -0.0061(12) C5 0.0595(15) 0.0680(17) 0.0681(16) -0.0101(13) 0.0306(13) -0.0087(13) C6 0.0484(14) 0.0707(18) 0.0650(16) -0.0033(12) 0.0242(13) 0.0111(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 N1 C1 1.310(3) . ? N1 N2 1.381(2) . ? N2 C3 1.309(3) 3_656 ? C1 C2 1.417(3) . ? C1 C6 1.499(3) . ? C2 C2 1.373(3) 3_656 ? C2 C3 1.417(3) . ? C3 N2 1.309(3) 3_656 ? C3 C4 1.492(3) . ? C4 C5 1.518(3) . ? C4 H1 0.98(2) . ? C4 H2 0.98(2) . ? C5 C6 1.526(3) . ? C5 H3 1.01(2) . ? C5 H4 1.01(2) . ? C6 H5 1.04(2) . ? C6 H6 0.95(2) . ? 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 C1 N1 N2 120.01(17) . . ? C3 N2 N1 120.67(18) 3_656 . ? N1 C1 C2 121.89(19) . . ? N1 C1 C6 120.07(18) . . ? C2 C1 C6 118.0(2) . . ? C2 C2 C3 118.3(2) 3_656 . ? C2 C2 C1 117.8(2) 3_656 . ? C3 C2 C1 123.94(17) . . ? N2 C3 C2 121.33(19) 3_656 . ? N2 C3 C4 120.3(2) 3_656 . ? C2 C3 C4 118.39(18) . . ? C3 C4 C5 111.3(2) . . ? C3 C4 H1 105.8(12) . . ? C5 C4 H1 110.6(12) . . ? C3 C4 H2 108.6(13) . . ? C5 C4 H2 111.0(13) . . ? H1 C4 H2 109.4(18) . . ? C4 C5 C6 111.2(2) . . ? C4 C5 H3 111.1(13) . . ? C6 C5 H3 109.2(14) . . ? C4 C5 H4 108.6(14) . . ? C6 C5 H4 110.1(13) . . ? H3 C5 H4 106.5(19) . . ? C1 C6 C5 110.70(19) . . ? C1 C6 H5 107.1(12) . . ? C5 C6 H5 110.5(12) . . ? C1 C6 H6 109.2(14) . . ? C5 C6 H6 111.1(15) . . ? H5 C6 H6 108.2(19) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.157 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.036 #========================================================== # END of CIF #==========================================================