# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_ss-69 #TrackingRef '10183_web_deposit_cif_file_0_SUMITKUMARPANJA_1331910038.DNDPQ CIF CCDC.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6-nitro-2-(2-nitro-phenyl)-4-phenyl-quinazoline _chemical_melting_point ? _chemical_formula_moiety 'C20 H12 N4 O4' _chemical_formula_sum 'C20 H12 N4 O4' _chemical_formula_weight 372.34 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_space_group_name_Hall '-P 2yn' 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 10.7619(5) _cell_length_b 7.9318(4) _cell_length_c 19.9964(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.129(4) _cell_angle_gamma 90.00 _cell_volume 1697.16(14) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used '\w scans' _cell_measurement_theta_min 3.2880 _cell_measurement_theta_max 28.9717 _exptl_crystal_description rectangular _exptl_crystal_colour brown _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.939 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _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 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0938 _diffrn_standards_number 8080 _diffrn_standards_interval_count 0.0186 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7709 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0776 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 29.04 _reflns_number_total 3873 _reflns_number_gt 2613 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _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^)+(0.0426P)^2^+0.6252P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3873 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0839 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1273 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 N3 N 0.74004(13) 0.2706(2) 0.13151(8) 0.0414(4) Uani 1 1 d . . . N4 N 0.55772(14) 0.2824(2) 0.05159(8) 0.0452(4) Uani 1 1 d . . . C7 C 0.67965(16) 0.3383(2) 0.17913(9) 0.0384(4) Uani 1 1 d . . . C1 C 0.55319(16) 0.3948(2) 0.16460(9) 0.0393(4) Uani 1 1 d . . . C2 C 0.49523(16) 0.3600(2) 0.09917(10) 0.0417(4) Uani 1 1 d . . . C14 C 0.67604(17) 0.2507(2) 0.06941(9) 0.0404(4) Uani 1 1 d . . . N2 N 0.92227(17) 0.3814(2) 0.04988(9) 0.0538(5) Uani 1 1 d . . . C8 C 0.75208(17) 0.3507(2) 0.24637(9) 0.0400(4) Uani 1 1 d . . . C6 C 0.48690(17) 0.4877(2) 0.20939(10) 0.0435(5) Uani 1 1 d . . . H009 H 0.5242 0.5166 0.2520 0.052 Uiso 1 1 calc R . . C15 C 0.74978(17) 0.1832(2) 0.01672(9) 0.0408(4) Uani 1 1 d . . . C5 C 0.36700(18) 0.5342(3) 0.18885(11) 0.0479(5) Uani 1 1 d . . . C20 C 0.70313(19) 0.0571(3) -0.02729(10) 0.0500(5) Uani 1 1 d . . . H012 H 0.6239 0.0135 -0.0236 0.060 Uiso 1 1 calc R . . O4 O 0.85692(16) 0.5059(2) 0.05503(9) 0.0708(5) Uani 1 1 d . . . C016 C 0.86931(18) 0.2406(2) 0.00882(10) 0.0435(5) Uani 1 1 d . . . C13 C 0.87674(17) 0.3996(3) 0.25077(10) 0.0465(5) Uani 1 1 d . . . H015 H 0.9123 0.4287 0.2120 0.056 Uiso 1 1 calc R . . C4 C 0.30700(19) 0.4969(3) 0.12531(12) 0.0558(6) Uani 1 1 d . . . H016 H 0.2247 0.5300 0.1134 0.067 Uiso 1 1 calc R . . C3 C 0.37060(18) 0.4116(3) 0.08114(11) 0.0544(5) Uani 1 1 d . . . H017 H 0.3317 0.3868 0.0385 0.065 Uiso 1 1 calc R . . C9 C 0.70099(19) 0.3058(3) 0.30506(10) 0.0481(5) Uani 1 1 d . . . H018 H 0.6175 0.2739 0.3030 0.058 Uiso 1 1 calc R . . C17 C 0.93988(19) 0.1791(3) -0.03916(11) 0.0545(5) Uani 1 1 d . . . H019 H 1.0201 0.2199 -0.0423 0.065 Uiso 1 1 calc R . . O1 O 0.35355(17) 0.6858(3) 0.28672(9) 0.0852(6) Uani 1 1 d . . . N1 N 0.29753(19) 0.6322(3) 0.23505(11) 0.0649(5) Uani 1 1 d . . . C19 C 0.7716(2) -0.0048(3) -0.07620(11) 0.0573(6) Uani 1 1 d . . . H022 H 0.7379 -0.0884 -0.1053 0.069 Uiso 1 1 calc R . . C12 C 0.94809(19) 0.4054(3) 0.31235(11) 0.0566(6) Uani 1 1 d . . . H023 H 1.0306 0.4417 0.3151 0.068 Uiso 1 1 calc R . . O3 O 1.02915(15) 0.3705(3) 0.07461(10) 0.0866(6) Uani 1 1 d . . . C11 C 0.8969(2) 0.3570(3) 0.36998(12) 0.0617(6) Uani 1 1 d . . . H025 H 0.9457 0.3575 0.4113 0.074 Uiso 1 1 calc R . . C10 C 0.7736(2) 0.3083(3) 0.36611(11) 0.0574(6) Uani 1 1 d . . . H026 H 0.7391 0.2770 0.4050 0.069 Uiso 1 1 calc R . . C18 C 0.8897(2) 0.0562(3) -0.08240(11) 0.0584(6) Uani 1 1 d . . . H027 H 0.9352 0.0144 -0.1157 0.070 Uiso 1 1 calc R . . O2 O 0.18744(18) 0.6566(4) 0.21953(12) 0.1237(9) 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 N3 0.0396(8) 0.0458(9) 0.0384(9) 0.0001(7) 0.0021(7) -0.0042(7) N4 0.0416(9) 0.0515(10) 0.0417(9) -0.0003(8) 0.0009(7) -0.0047(8) C7 0.0397(9) 0.0367(10) 0.0388(10) 0.0042(8) 0.0041(8) -0.0055(8) C1 0.0385(9) 0.0384(10) 0.0412(10) 0.0054(8) 0.0051(8) -0.0071(8) C2 0.0371(9) 0.0437(11) 0.0444(11) 0.0041(9) 0.0041(8) -0.0054(9) C14 0.0407(10) 0.0414(11) 0.0391(10) 0.0016(8) 0.0040(8) -0.0059(8) N2 0.0513(10) 0.0571(12) 0.0547(11) -0.0050(9) 0.0133(8) -0.0131(10) C8 0.0439(10) 0.0353(10) 0.0401(10) 0.0002(8) 0.0006(8) 0.0016(8) C6 0.0463(11) 0.0423(11) 0.0427(11) 0.0054(9) 0.0080(9) -0.0030(9) C15 0.0421(10) 0.0437(11) 0.0360(10) 0.0030(8) 0.0013(8) -0.0017(9) C5 0.0457(11) 0.0453(12) 0.0547(13) 0.0079(10) 0.0152(9) 0.0009(9) C20 0.0499(11) 0.0563(13) 0.0432(11) -0.0026(10) 0.0018(9) -0.0115(10) O4 0.0857(12) 0.0464(9) 0.0826(12) -0.0083(8) 0.0190(9) -0.0050(9) C016 0.0473(11) 0.0417(11) 0.0413(11) -0.0007(8) 0.0036(8) -0.0037(9) C13 0.0455(11) 0.0446(12) 0.0492(12) -0.0035(9) 0.0036(9) 0.0014(9) C4 0.0377(10) 0.0610(14) 0.0685(15) 0.0027(12) 0.0041(10) 0.0015(10) C3 0.0420(11) 0.0637(14) 0.0555(13) 0.0008(11) -0.0048(9) -0.0030(10) C9 0.0543(12) 0.0452(12) 0.0446(11) 0.0004(9) 0.0039(9) -0.0033(10) C17 0.0488(12) 0.0581(14) 0.0585(14) -0.0031(11) 0.0144(10) -0.0058(10) O1 0.0897(13) 0.1080(16) 0.0609(11) -0.0056(11) 0.0223(10) 0.0232(12) N1 0.0606(12) 0.0691(14) 0.0676(14) 0.0058(11) 0.0189(10) 0.0159(11) C19 0.0711(15) 0.0561(14) 0.0442(12) -0.0081(10) 0.0042(10) -0.0084(12) C12 0.0450(11) 0.0590(14) 0.0630(15) -0.0155(11) -0.0065(10) 0.0032(10) O3 0.0512(10) 0.1037(15) 0.1020(15) -0.0352(12) -0.0059(9) -0.0129(10) C11 0.0722(15) 0.0630(15) 0.0462(13) -0.0120(11) -0.0115(11) 0.0120(13) C10 0.0770(16) 0.0545(13) 0.0404(12) -0.0003(10) 0.0046(10) 0.0012(12) C18 0.0683(14) 0.0593(14) 0.0500(13) -0.0082(11) 0.0169(11) -0.0015(12) O2 0.0694(13) 0.167(2) 0.134(2) -0.0437(17) 0.0109(12) 0.0480(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 N3 C7 1.322(2) . ? N3 C14 1.363(2) . ? N4 C14 1.310(2) . ? N4 C2 1.368(2) . ? C7 C1 1.433(2) . ? C7 C8 1.484(2) . ? C1 C6 1.411(3) . ? C1 C2 1.415(3) . ? C2 C3 1.412(3) . ? C14 C15 1.485(3) . ? N2 O3 1.206(2) . ? N2 O4 1.223(2) . ? N2 C016 1.466(3) . ? C8 C13 1.390(3) . ? C8 C9 1.394(3) . ? C6 C5 1.362(3) . ? C6 H009 0.9300 . ? C15 C016 1.389(3) . ? C15 C20 1.390(3) . ? C5 C4 1.394(3) . ? C5 N1 1.471(3) . ? C20 C19 1.376(3) . ? C20 H012 0.9300 . ? C016 C17 1.375(3) . ? C13 C12 1.381(3) . ? C13 H015 0.9300 . ? C4 C3 1.355(3) . ? C4 H016 0.9300 . ? C3 H017 0.9300 . ? C9 C10 1.378(3) . ? C9 H018 0.9300 . ? C17 C18 1.375(3) . ? C17 H019 0.9300 . ? O1 N1 1.216(3) . ? N1 O2 1.208(2) . ? C19 C18 1.377(3) . ? C19 H022 0.9300 . ? C12 C11 1.384(3) . ? C12 H023 0.9300 . ? C11 C10 1.375(3) . ? C11 H025 0.9300 . ? C10 H026 0.9300 . ? C18 H027 0.9300 . ? 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 C7 N3 C14 117.62(16) . . ? C14 N4 C2 115.66(16) . . ? N3 C7 C1 120.68(16) . . ? N3 C7 C8 115.37(16) . . ? C1 C7 C8 123.96(17) . . ? C6 C1 C2 119.09(17) . . ? C6 C1 C7 124.65(17) . . ? C2 C1 C7 116.19(17) . . ? N4 C2 C3 118.48(17) . . ? N4 C2 C1 121.99(16) . . ? C3 C2 C1 119.49(18) . . ? N4 C14 N3 127.40(17) . . ? N4 C14 C15 117.00(16) . . ? N3 C14 C15 115.59(16) . . ? O3 N2 O4 123.8(2) . . ? O3 N2 C016 118.13(19) . . ? O4 N2 C016 118.03(17) . . ? C13 C8 C9 118.86(18) . . ? C13 C8 C7 119.07(17) . . ? C9 C8 C7 121.97(17) . . ? C5 C6 C1 118.47(19) . . ? C5 C6 H009 120.8 . . ? C1 C6 H009 120.8 . . ? C016 C15 C20 116.10(17) . . ? C016 C15 C14 122.27(17) . . ? C20 C15 C14 121.63(17) . . ? C6 C5 C4 123.29(19) . . ? C6 C5 N1 118.82(19) . . ? C4 C5 N1 117.88(19) . . ? C19 C20 C15 121.45(19) . . ? C19 C20 H012 119.3 . . ? C15 C20 H012 119.3 . . ? C17 C016 C15 123.38(18) . . ? C17 C016 N2 116.79(17) . . ? C15 C016 N2 119.71(17) . . ? C12 C13 C8 120.4(2) . . ? C12 C13 H015 119.8 . . ? C8 C13 H015 119.8 . . ? C3 C4 C5 118.89(19) . . ? C3 C4 H016 120.6 . . ? C5 C4 H016 120.6 . . ? C4 C3 C2 120.7(2) . . ? C4 C3 H017 119.6 . . ? C2 C3 H017 119.6 . . ? C10 C9 C8 120.3(2) . . ? C10 C9 H018 119.9 . . ? C8 C9 H018 119.9 . . ? C18 C17 C016 118.75(19) . . ? C18 C17 H019 120.6 . . ? C016 C17 H019 120.6 . . ? O2 N1 O1 123.1(2) . . ? O2 N1 C5 118.3(2) . . ? O1 N1 C5 118.64(19) . . ? C20 C19 C18 120.5(2) . . ? C20 C19 H022 119.7 . . ? C18 C19 H022 119.7 . . ? C13 C12 C11 120.0(2) . . ? C13 C12 H023 120.0 . . ? C11 C12 H023 120.0 . . ? C10 C11 C12 119.9(2) . . ? C10 C11 H025 120.1 . . ? C12 C11 H025 120.1 . . ? C11 C10 C9 120.4(2) . . ? C11 C10 H026 119.8 . . ? C9 C10 H026 119.8 . . ? C17 C18 C19 119.8(2) . . ? C17 C18 H027 120.1 . . ? C19 C18 H027 120.1 . . ? _diffrn_measured_fraction_theta_max 0.853 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.329 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 871913' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_ss-96a #TrackingRef 'SKP-6Cl-2OH_Dihydro-quinazoline.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(6-chloro-4-phenyl-1,2-dihydroquinolin-2-yl)phenol ; _chemical_name_common ? _chemical_melting_point 438.5 _chemical_formula_moiety 'C20 H15 Cl N2 O' _chemical_formula_sum 'C20 H15 Cl N2 O' _chemical_formula_weight 334.79 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.8795(7) _cell_length_b 10.8790(8) _cell_length_c 19.733(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1691.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1253 _cell_measurement_theta_min 3.1858 _cell_measurement_theta_max 28.9321 _exptl_crystal_description rectangular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_crystal_F_000' 696.84 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91398 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0938 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5111 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 29.00 _reflns_number_total 3457 _reflns_number_gt 2696 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0521P)^2^+0.2902P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(11) _refine_ls_number_reflns 3457 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.1147 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 Cl1 Cl 0.24864(14) 0.92780(9) 0.35367(4) 0.0704(3) Uani 1 1 d . . . O1 O 0.0046(3) 0.7497(2) 0.74619(13) 0.0611(6) Uani 1 1 d . . . H1 H 0.0104 0.6855 0.7678 0.092 Uiso 1 1 calc R . . N1 N -0.0756(3) 0.8863(2) 0.62142(13) 0.0409(6) Uani 1 1 d . . . N3 N 0.0307(3) 1.08577(19) 0.65136(12) 0.0418(6) Uani 1 1 d . . . C10 C 0.0781(4) 1.0029(2) 0.53949(14) 0.0347(6) Uani 1 1 d . . . C9 C -0.0020(3) 0.8924(2) 0.55801(14) 0.0337(6) Uani 1 1 d . . . C4 C 0.0678(4) 1.1043(2) 0.58889(15) 0.0386(7) Uani 1 1 d . . . C22 C 0.3338(4) 0.9485(3) 0.68457(16) 0.0507(8) Uani 1 1 d . . . H20 H 0.3435 1.0205 0.6594 0.061 Uiso 1 1 calc R . . C17 C 0.1747(4) 0.9025(2) 0.69786(14) 0.0393(7) Uani 1 1 d . . . C6 C 0.1464(4) 0.9164(3) 0.43176(15) 0.0428(7) Uani 1 1 d . . . C7 C 0.0604(4) 0.8087(3) 0.44862(17) 0.0463(8) Uani 1 1 d . . . H4 H 0.0521 0.7451 0.4173 0.056 Uiso 1 1 calc R . . C5 C 0.1555(4) 1.0130(3) 0.47626(15) 0.0390(7) Uani 1 1 d . . . H2 H 0.2128 1.0846 0.4643 0.047 Uiso 1 1 calc R . . C8 C -0.0114(4) 0.7969(2) 0.51100(15) 0.0415(7) Uani 1 1 d . . . H5 H -0.0673 0.7245 0.5224 0.050 Uiso 1 1 calc R . . C18 C 0.1629(5) 0.7940(3) 0.73537(16) 0.0487(8) Uani 1 1 d . . . C2 C 0.0092(4) 0.9584(2) 0.67408(15) 0.0389(7) Uani 1 1 d . . . C11 C 0.1011(4) 1.2346(2) 0.56819(17) 0.0413(7) Uani 1 1 d . . . C12 C 0.1890(5) 1.3116(3) 0.61138(19) 0.0561(9) Uani 1 1 d . . . H10 H 0.2281 1.2812 0.6526 0.067 Uiso 1 1 calc R . . C16 C 0.0451(4) 1.2806(3) 0.5072(2) 0.0553(9) Uani 1 1 d . . . H14 H -0.0147 1.2304 0.4774 0.066 Uiso 1 1 calc R . . C20 C 0.4653(5) 0.7837(4) 0.7437(2) 0.0741(12) Uani 1 1 d . . . H18 H 0.5625 0.7432 0.7584 0.089 Uiso 1 1 calc R . . C13 C 0.2201(5) 1.4332(3) 0.5947(3) 0.0743(12) Uani 1 1 d . . . H11 H 0.2778 1.4843 0.6247 0.089 Uiso 1 1 calc R . . C21 C 0.4798(5) 0.8913(4) 0.70730(19) 0.0656(10) Uani 1 1 d . . . H19 H 0.5860 0.9249 0.6982 0.079 Uiso 1 1 calc R . . C14 C 0.1648(5) 1.4774(3) 0.5335(3) 0.0811(15) Uani 1 1 d . . . H12 H 0.1863 1.5586 0.5216 0.097 Uiso 1 1 calc R . . C19 C 0.3095(5) 0.7363(3) 0.7582(2) 0.0652(10) Uani 1 1 d . . . H17 H 0.3012 0.6647 0.7837 0.078 Uiso 1 1 calc R . . C15 C 0.0785(5) 1.4028(3) 0.4901(3) 0.0756(12) Uani 1 1 d . . . H13 H 0.0414 1.4336 0.4487 0.091 Uiso 1 1 calc R . . H8 H -0.067(3) 0.959(2) 0.7112(13) 0.030(7) Uiso 1 1 d . . . H22 H -0.105(5) 0.813(3) 0.6352(17) 0.062(11) 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 Cl1 0.0922(7) 0.0775(6) 0.0416(4) -0.0030(5) 0.0196(5) -0.0012(6) O1 0.0689(15) 0.0565(13) 0.0578(14) 0.0273(12) -0.0052(13) -0.0111(12) N1 0.0510(15) 0.0330(13) 0.0386(14) 0.0038(12) 0.0030(13) -0.0047(12) N3 0.0581(16) 0.0288(11) 0.0384(13) 0.0004(11) 0.0030(13) 0.0017(11) C10 0.0402(15) 0.0315(13) 0.0325(15) 0.0013(12) -0.0036(13) 0.0000(12) C9 0.0360(14) 0.0304(13) 0.0348(15) 0.0034(12) -0.0039(13) 0.0019(11) C4 0.0441(16) 0.0300(13) 0.0417(17) 0.0000(13) -0.0014(14) 0.0016(12) C22 0.064(2) 0.0467(16) 0.0416(18) -0.0025(16) 0.0009(18) -0.0039(16) C17 0.0549(17) 0.0344(14) 0.0288(14) -0.0012(13) 0.0025(14) -0.0017(14) C6 0.0488(17) 0.0481(16) 0.0314(14) -0.0018(15) 0.0023(14) 0.0086(15) C7 0.0526(18) 0.0431(16) 0.0432(18) -0.0106(15) -0.0038(16) 0.0021(14) C5 0.0408(15) 0.0370(14) 0.0394(16) 0.0058(13) -0.0010(14) -0.0001(13) C8 0.0438(16) 0.0327(14) 0.0479(18) 0.0004(14) -0.0032(16) -0.0025(13) C18 0.065(2) 0.0429(16) 0.0386(17) 0.0009(15) -0.0046(17) -0.0056(16) C2 0.0531(18) 0.0313(13) 0.0321(14) -0.0004(12) 0.0092(15) 0.0016(13) C11 0.0434(16) 0.0298(13) 0.0508(18) 0.0016(14) 0.0040(15) 0.0018(12) C12 0.065(2) 0.0399(16) 0.063(2) -0.0078(16) 0.005(2) -0.0089(16) C16 0.0502(19) 0.0428(17) 0.073(2) 0.0173(18) -0.0012(19) 0.0043(14) C20 0.068(3) 0.079(3) 0.076(3) -0.001(2) -0.025(2) 0.018(2) C13 0.072(3) 0.0397(19) 0.111(3) -0.013(2) 0.028(3) -0.0128(19) C21 0.055(2) 0.076(3) 0.066(2) -0.010(2) -0.003(2) 0.0007(19) C14 0.060(2) 0.0347(17) 0.148(5) 0.017(3) 0.033(3) -0.0030(18) C19 0.080(3) 0.0524(19) 0.063(2) 0.0097(19) -0.017(2) 0.007(2) C15 0.060(2) 0.060(2) 0.106(3) 0.045(2) 0.012(2) 0.0153(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 Cl1 C6 1.743(3) . ? O1 C18 1.354(4) . ? O1 H1 0.8200 . ? N1 C9 1.381(4) . ? N1 C2 1.463(4) . ? N1 H22 0.87(3) . ? N3 C4 1.283(4) . ? N3 C2 1.466(3) . ? C10 C5 1.393(4) . ? C10 C9 1.407(4) . ? C10 C4 1.474(4) . ? C9 C8 1.394(4) . ? C4 C11 1.499(4) . ? C22 C17 1.376(4) . ? C22 C21 1.383(5) . ? C22 H20 0.9300 . ? C17 C18 1.396(4) . ? C17 C2 1.513(4) . ? C6 C5 1.372(4) . ? C6 C7 1.393(4) . ? C7 C8 1.361(4) . ? C7 H4 0.9300 . ? C5 H2 0.9300 . ? C8 H5 0.9300 . ? C18 C19 1.390(5) . ? C2 H8 0.95(3) . ? C11 C16 1.376(5) . ? C11 C12 1.381(4) . ? C12 C13 1.385(5) . ? C12 H10 0.9300 . ? C16 C15 1.397(5) . ? C16 H14 0.9300 . ? C20 C19 1.362(6) . ? C20 C21 1.378(6) . ? C20 H18 0.9300 . ? C13 C14 1.370(6) . ? C13 H11 0.9300 . ? C21 H19 0.9300 . ? C14 C15 1.362(6) . ? C14 H12 0.9300 . ? C19 H17 0.9300 . ? C15 H13 0.9300 . ? 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 109.5 . . ? C9 N1 C2 115.2(2) . . ? C9 N1 H22 116(2) . . ? C2 N1 H22 113(2) . . ? C4 N3 C2 117.9(2) . . ? C5 C10 C9 119.8(2) . . ? C5 C10 C4 123.9(3) . . ? C9 C10 C4 116.3(2) . . ? N1 C9 C8 123.0(2) . . ? N1 C9 C10 117.7(2) . . ? C8 C9 C10 119.2(3) . . ? N3 C4 C10 122.1(2) . . ? N3 C4 C11 116.7(3) . . ? C10 C4 C11 121.2(3) . . ? C17 C22 C21 122.2(3) . . ? C17 C22 H20 118.9 . . ? C21 C22 H20 118.9 . . ? C22 C17 C18 118.0(3) . . ? C22 C17 C2 125.5(3) . . ? C18 C17 C2 116.6(3) . . ? C5 C6 C7 121.1(3) . . ? C5 C6 Cl1 119.2(2) . . ? C7 C6 Cl1 119.7(2) . . ? C8 C7 C6 119.8(3) . . ? C8 C7 H4 120.1 . . ? C6 C7 H4 120.1 . . ? C6 C5 C10 119.3(3) . . ? C6 C5 H2 120.3 . . ? C10 C5 H2 120.3 . . ? C7 C8 C9 120.6(3) . . ? C7 C8 H5 119.7 . . ? C9 C8 H5 119.7 . . ? O1 C18 C19 123.7(3) . . ? O1 C18 C17 116.4(3) . . ? C19 C18 C17 119.9(3) . . ? N1 C2 N3 110.0(2) . . ? N1 C2 C17 113.5(2) . . ? N3 C2 C17 112.0(2) . . ? N1 C2 H8 105.4(16) . . ? N3 C2 H8 107.6(16) . . ? C17 C2 H8 108.0(16) . . ? C16 C11 C12 118.7(3) . . ? C16 C11 C4 121.7(3) . . ? C12 C11 C4 119.6(3) . . ? C11 C12 C13 121.4(4) . . ? C11 C12 H10 119.3 . . ? C13 C12 H10 119.3 . . ? C11 C16 C15 119.8(4) . . ? C11 C16 H14 120.1 . . ? C15 C16 H14 120.1 . . ? C19 C20 C21 120.4(4) . . ? C19 C20 H18 119.8 . . ? C21 C20 H18 119.8 . . ? C14 C13 C12 119.2(4) . . ? C14 C13 H11 120.4 . . ? C12 C13 H11 120.4 . . ? C20 C21 C22 118.8(4) . . ? C20 C21 H19 120.6 . . ? C22 C21 H19 120.6 . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H12 119.9 . . ? C13 C14 H12 119.9 . . ? C20 C19 C18 120.6(3) . . ? C20 C19 H17 119.7 . . ? C18 C19 H17 119.7 . . ? C14 C15 C16 120.6(4) . . ? C14 C15 H13 119.7 . . ? C16 C15 H13 119.7 . . ? _diffrn_measured_fraction_theta_max 0.866 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.512 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.041 _database_code_depnum_ccdc_archive 'CCDC 915059'