# 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_I _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C20 H17 N3 O2' _chemical_formula_sum 'C20 H17 N3 O2' _chemical_formula_iupac ? _chemical_formula_weight 331.37 _chemical_absolute_configuration ? _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.358(2) _cell_length_b 6.1406(18) _cell_length_c 16.069(4) _cell_angle_alpha 90 _cell_angle_beta 93.667(15) _cell_angle_gamma 90 _cell_volume 823.0(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 521 _cell_measurement_theta_min 2.4417 _cell_measurement_theta_max 19.6745 _cell_measurement_temperature 250.(2) _exptl_crystal_description rodshaped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.5982 _exptl_absorpt_correction_T_max 0.7452 _exptl_special_details ; ; _diffrn_ambient_temperature 250.(2) _diffrn_source 'sealed tube' _diffrn_source_type 'fine focus' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker kappa Apex2' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 4273 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0864 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 25.13 _diffrn_reflns_theta_full 25.13 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _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. ; _reflns_number_total 2241 _reflns_number_gt 1265 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1247 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_gt 0.0691 _refine_ls_wR_factor_ref 0.0828 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _refine_ls_number_reflns 2241 _refine_ls_number_parameters 229 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment undef _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0152P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.182 _refine_diff_density_min -0.224 _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 0.0(5) 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' _computing_data_collection ? _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.9296(3) 0.7620(6) 0.33936(17) 0.0523(9) Uani d . 1 . . O O2 0.8726(4) -0.2424(7) 0.93178(18) 0.0652(11) Uani d . 1 . . N N1 0.6628(4) 0.5190(6) 0.6865(2) 0.0411(11) Uani d . 1 . . N N2 0.3997(5) 0.6186(7) 0.8573(2) 0.0502(12) Uani d . 1 . . N N3 0.4357(4) 0.8003(7) 0.7379(2) 0.0476(12) Uani d . 1 . . C C1 0.9182(5) 0.9542(8) 0.2894(2) 0.0640(16) Uani d . 1 . . H H1A 0.9523 1.079 0.3231 0.096 Uiso calc R 1 . . H H1B 0.808 0.9747 0.2681 0.096 Uiso calc R 1 . . H H1C 0.9865 0.9397 0.2432 0.096 Uiso calc R 1 . . C C2 0.8456(5) 0.7590(10) 0.4099(3) 0.0444(14) Uani d . 1 . . C C3 0.8628(5) 0.5709(9) 0.4570(3) 0.0474(14) Uani d . 1 . . H H3 0.9263 0.4556 0.4392 0.057 Uiso calc R 1 . . C C4 0.7859(5) 0.5535(8) 0.5306(3) 0.0473(14) Uani d . 1 . . H H4 0.7978 0.4243 0.5618 0.057 Uiso calc R 1 . . C C5 0.6927(5) 0.7184(8) 0.5598(3) 0.0391(13) Uani d . 1 . . C C6 0.6137(5) 0.6957(8) 0.6390(3) 0.0419(13) Uani d . 1 . . C C7 0.6022(5) 0.4809(8) 0.7596(3) 0.0412(14) Uani d . 1 . . C C8 0.6633(5) 0.2909(9) 0.8077(2) 0.0383(12) Uani d . 1 . . C C9 0.7658(5) 0.1477(8) 0.7695(2) 0.0424(13) Uani d . 1 . . H H9 0.7897 0.1721 0.7139 0.051 Uiso calc R 1 . . C C10 0.8320(5) -0.0279(8) 0.8118(3) 0.0481(14) Uani d . 1 . . H H10 0.9007 -0.1232 0.7854 0.058 Uiso calc R 1 . . C C11 0.7960(6) -0.0637(10) 0.8947(3) 0.0539(15) Uani d . 1 . . C C12 0.8394(5) -0.2816(11) 1.0165(3) 0.099(2) Uani d . 1 . . H H12A 0.7263 -0.3136 1.0197 0.149 Uiso calc R 1 . . H H12B 0.8669 -0.1533 1.0497 0.149 Uiso calc R 1 . . H H12C 0.9024 -0.4044 1.0378 0.149 Uiso calc R 1 . . C C13 0.7533(5) 0.9254(9) 0.4361(3) 0.0556(15) Uani d . 1 . . H H13 0.7407 1.0531 0.404 0.067 Uiso calc R 1 . . C C14 0.6769(5) 0.9054(9) 0.5112(3) 0.0550(15) Uani d . 1 . . H H14 0.6138 1.0211 0.5289 0.066 Uiso calc R 1 . . C C15 0.4823(5) 0.6222(8) 0.7891(3) 0.0395(13) Uani d . 1 . . C C16 0.2984(6) 0.7956(9) 0.8487(3) 0.0567(15) Uani d . 1 . . H H16 0.2251 0.8347 0.8881 0.068 Uiso calc R 1 . . C C17 0.3165(5) 0.9080(8) 0.7761(3) 0.0536(15) Uani d . 1 . . H H17 0.2596 1.032 0.7567 0.064 Uiso calc R 1 . . C C18 0.5010(5) 0.8371(8) 0.6639(3) 0.0429(14) Uani d . 1 . . H H18 0.4691 0.9574 0.6306 0.051 Uiso calc R 1 . . C C19 0.6942(6) 0.0727(8) 0.9334(3) 0.0532(15) Uani d . 1 . . H H19 0.6691 0.0465 0.9887 0.064 Uiso calc R 1 . . C C20 0.6286(5) 0.2504(9) 0.8896(2) 0.0547(15) Uani d . 1 . . H H20 0.5594 0.345 0.9161 0.066 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.057(2) 0.051(3) 0.0494(19) 0.005(2) 0.0109(16) 0.018(2) O2 0.070(3) 0.057(3) 0.069(2) 0.008(2) 0.0130(18) 0.023(3) N1 0.040(3) 0.046(3) 0.038(2) 0.001(2) 0.0072(19) 0.006(2) N2 0.051(3) 0.053(3) 0.047(3) 0.004(3) 0.009(2) -0.008(2) N3 0.040(3) 0.052(4) 0.050(3) 0.003(3) 0.004(2) -0.012(3) C1 0.060(3) 0.072(4) 0.062(3) 0.010(3) 0.012(3) 0.025(3) C2 0.042(3) 0.047(4) 0.043(3) -0.001(3) -0.002(2) 0.007(4) C3 0.051(3) 0.046(4) 0.046(3) 0.008(3) 0.004(3) 0.001(3) C4 0.056(3) 0.041(4) 0.046(3) 0.002(3) 0.008(3) 0.004(3) C5 0.035(3) 0.040(4) 0.041(3) 0.001(3) -0.003(2) 0.006(3) C6 0.037(3) 0.043(4) 0.045(3) -0.004(3) 0.001(2) 0.004(3) C7 0.037(3) 0.041(4) 0.045(3) -0.009(3) 0.003(2) -0.003(3) C8 0.041(3) 0.037(4) 0.038(3) 0.003(3) 0.008(2) -0.002(3) C9 0.045(3) 0.041(4) 0.040(3) -0.004(3) -0.003(2) 0.008(3) C10 0.053(3) 0.042(4) 0.050(3) 0.000(3) 0.008(3) 0.001(3) C11 0.047(3) 0.058(5) 0.056(3) -0.012(3) -0.004(3) 0.016(4) C12 0.089(5) 0.118(6) 0.093(4) 0.026(4) 0.029(3) 0.064(5) C13 0.059(4) 0.048(4) 0.061(4) 0.011(3) 0.009(3) 0.023(3) C14 0.055(3) 0.045(4) 0.067(4) 0.013(3) 0.017(3) 0.000(3) C15 0.036(3) 0.037(4) 0.045(3) -0.002(3) 0.003(2) 0.000(3) C16 0.052(3) 0.053(4) 0.066(4) 0.011(3) 0.007(3) -0.019(3) C17 0.049(4) 0.045(4) 0.067(4) 0.020(3) 0.010(3) -0.013(3) C18 0.044(3) 0.040(4) 0.044(3) 0.000(3) 0.001(2) 0.004(3) C19 0.067(4) 0.049(4) 0.046(3) 0.011(3) 0.020(3) 0.009(3) C20 0.061(4) 0.060(4) 0.044(3) 0.003(3) 0.014(2) 0.002(3) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 . 1.371(5) ? O1 C1 . 1.427(5) ? O2 C11 . 1.386(6) ? O2 C12 . 1.427(4) ? N1 C7 . 1.330(4) ? N1 C6 . 1.374(5) ? N2 C15 . 1.331(5) ? N2 C16 . 1.379(6) ? N3 C18 . 1.360(5) ? N3 C17 . 1.372(5) ? N3 C15 . 1.408(5) ? C1 H1A . 0.97 ? C1 H1B . 0.97 ? C1 H1C . 0.97 ? C2 C13 . 1.363(6) ? C2 C3 . 1.383(7) ? C3 C4 . 1.385(5) ? C3 H3 . 0.94 ? C4 C5 . 1.378(6) ? C4 H4 . 0.94 ? C5 C14 . 1.390(6) ? C5 C6 . 1.477(5) ? C6 C18 . 1.359(6) ? C7 C15 . 1.429(5) ? C7 C8 . 1.473(6) ? C8 C20 . 1.389(5) ? C8 C9 . 1.396(5) ? C9 C10 . 1.372(5) ? C9 H9 . 0.94 ? C10 C11 . 1.402(5) ? C10 H10 . 0.94 ? C11 C19 . 1.371(6) ? C12 H12A . 0.97 ? C12 H12B . 0.97 ? C12 H12C . 0.97 ? C13 C14 . 1.406(5) ? C13 H13 . 0.94 ? C14 H14 . 0.94 ? C16 C17 . 1.372(6) ? C16 H16 . 0.94 ? C17 H17 . 0.94 ? C18 H18 . 0.94 ? C19 C20 . 1.392(6) ? C19 H19 . 0.94 ? C20 H20 . 0.94 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 O1 C1 . . 117.2(4) ? C11 O2 C12 . . 115.5(4) ? C7 N1 C6 . . 120.8(4) ? C15 N2 C16 . . 104.6(4) ? C18 N3 C17 . . 130.9(5) ? C18 N3 C15 . . 121.9(4) ? C17 N3 C15 . . 107.2(4) ? O1 C1 H1A . . 109.5 ? O1 C1 H1B . . 109.5 ? H1A C1 H1B . . 109.5 ? O1 C1 H1C . . 109.5 ? H1A C1 H1C . . 109.5 ? H1B C1 H1C . . 109.5 ? C13 C2 O1 . . 125.1(5) ? C13 C2 C3 . . 119.9(5) ? O1 C2 C3 . . 115.0(5) ? C2 C3 C4 . . 119.6(5) ? C2 C3 H3 . . 120.2 ? C4 C3 H3 . . 120.2 ? C5 C4 C3 . . 122.5(5) ? C5 C4 H4 . . 118.8 ? C3 C4 H4 . . 118.8 ? C4 C5 C14 . . 116.8(4) ? C4 C5 C6 . . 121.2(5) ? C14 C5 C6 . . 122.0(4) ? C18 C6 N1 . . 121.9(4) ? C18 C6 C5 . . 123.3(5) ? N1 C6 C5 . . 114.7(4) ? N1 C7 C15 . . 120.1(5) ? N1 C7 C8 . . 117.6(4) ? C15 C7 C8 . . 122.3(4) ? C20 C8 C9 . . 118.4(5) ? C20 C8 C7 . . 123.5(5) ? C9 C8 C7 . . 118.1(4) ? C10 C9 C8 . . 121.1(4) ? C10 C9 H9 . . 119.4 ? C8 C9 H9 . . 119.4 ? C9 C10 C11 . . 119.3(5) ? C9 C10 H10 . . 120.4 ? C11 C10 H10 . . 120.4 ? C19 C11 O2 . . 124.9(5) ? C19 C11 C10 . . 120.8(5) ? O2 C11 C10 . . 114.3(5) ? O2 C12 H12A . . 109.5 ? O2 C12 H12B . . 109.5 ? H12A C12 H12B . . 109.5 ? O2 C12 H12C . . 109.5 ? H12A C12 H12C . . 109.5 ? H12B C12 H12C . . 109.5 ? C2 C13 C14 . . 119.7(5) ? C2 C13 H13 . . 120.1 ? C14 C13 H13 . . 120.1 ? C5 C14 C13 . . 121.5(5) ? C5 C14 H14 . . 119.3 ? C13 C14 H14 . . 119.3 ? N2 C15 N3 . . 110.8(4) ? N2 C15 C7 . . 132.4(5) ? N3 C15 C7 . . 116.9(4) ? C17 C16 N2 . . 112.4(4) ? C17 C16 H16 . . 123.8 ? N2 C16 H16 . . 123.8 ? N3 C17 C16 . . 105.0(4) ? N3 C17 H17 . . 127.5 ? C16 C17 H17 . . 127.5 ? C6 C18 N3 . . 118.4(5) ? C6 C18 H18 . . 120.8 ? N3 C18 H18 . . 120.8 ? C11 C19 C20 . . 119.1(5) ? C11 C19 H19 . . 120.5 ? C20 C19 H19 . . 120.5 ? C8 C20 C19 . . 121.3(5) ? C8 C20 H20 . . 119.4 ? C19 C20 H20 . . 119.4 ? _database_code_depnum_ccdc_archive 'CCDC 960038' ####################################################################### # # 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_I _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C19 H12 Cl N3 O' _chemical_formula_sum 'C19 H12 Cl N3 O' _chemical_formula_iupac ? _chemical_formula_weight 333.77 _chemical_melting_point ? _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.5494(4) _cell_length_b 11.2136(8) _cell_length_c 12.5273(10) _cell_angle_alpha 96.086(3) _cell_angle_beta 98.854(4) _cell_angle_gamma 98.261(3) _cell_volume 755.70(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1591 _cell_measurement_theta_min 2.6424 _cell_measurement_theta_max 23.7523 _cell_measurement_temperature 270.(2) _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.150 _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.263 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.6895 _exptl_absorpt_correction_T_max 0.7452 _exptl_special_details ; ; _diffrn_ambient_temperature 270.(2) _diffrn_source 'sealed tube' _diffrn_source_type 'fine focus' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 5562 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.14 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measured_fraction_theta_full 0.986 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _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. ; _reflns_number_total 2679 _reflns_number_gt 1844 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_gt 0.1006 _refine_ls_wR_factor_ref 0.1122 _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_restrained_S_all 1.146 _refine_ls_number_reflns 2679 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment undef _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.158 _refine_diff_density_min -0.199 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection ? _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl1 0.56845(12) 0.87741(6) 0.08988(6) 0.0645(3) Uani d . 1 . . O O1 1.6837(3) 0.13767(18) 0.65552(15) 0.0767(6) Uani d . 1 . . N N1 0.7349(3) 0.35962(17) 0.28074(15) 0.0466(5) Uani d . 1 . . N N2 0.3723(3) 0.16394(16) 0.20941(15) 0.0463(5) Uani d . 1 . . N N3 0.1309(3) 0.26420(18) 0.10441(16) 0.0530(5) Uani d . 1 . . C C1 0.5569(4) 0.7295(2) 0.1203(2) 0.0478(6) Uani d . 1 . . C C2 0.7634(4) 0.6983(2) 0.1802(2) 0.0597(7) Uani d . 1 . . H H2 0.9074 0.7548 0.202 0.072 Uiso calc R 1 . . C C3 0.7519(4) 0.5818(2) 0.2072(2) 0.0561(7) Uani d . 1 . . H H3 0.8907 0.5605 0.2476 0.067 Uiso calc R 1 . . C C4 0.5397(4) 0.4952(2) 0.17592(18) 0.0435(6) Uani d . 1 . . C C5 0.5409(4) 0.3737(2) 0.21059(18) 0.0427(6) Uani d . 1 . . C C6 0.7530(4) 0.2483(2) 0.31516(19) 0.0446(6) Uani d . 1 . . C C7 0.9794(4) 0.2433(2) 0.39391(19) 0.0449(6) Uani d . 1 . . C C8 1.0496(4) 0.1321(2) 0.4148(2) 0.0521(6) Uani d . 1 . . H H8 0.9554 0.0601 0.3777 0.063 Uiso calc R 1 . . C C9 1.2566(4) 0.1278(2) 0.48972(19) 0.0525(6) Uani d . 1 . . H H9 1.3009 0.053 0.5026 0.063 Uiso calc R 1 . . C C10 1.3989(4) 0.2334(2) 0.54577(19) 0.0506(6) Uani d . 1 . . C C11 1.6195(5) 0.2288(3) 0.6271(2) 0.0624(7) Uani d . 1 . . H H11 1.7164 0.3024 0.6587 0.075 Uiso calc R 1 . . C C12 0.3449(4) 0.6460(2) 0.0861(2) 0.0535(7) Uani d . 1 . . H H12 0.2082 0.6677 0.0444 0.064 Uiso calc R 1 . . C C13 0.3361(4) 0.5296(2) 0.11416(19) 0.0517(6) Uani d . 1 . . H H13 0.192 0.4733 0.0914 0.062 Uiso calc R 1 . . C C14 0.5754(4) 0.1507(2) 0.28168(18) 0.0478(6) Uani d . 1 . . H H14 0.5901 0.0766 0.3069 0.057 Uiso calc R 1 . . C C15 0.1651(4) 0.0827(2) 0.1634(2) 0.0538(6) Uani d . 1 . . H H15 0.1291 0.0013 0.1729 0.065 Uiso calc R 1 . . C C16 0.0231(4) 0.1467(2) 0.1006(2) 0.0565(7) Uani d . 1 . . H H16 -0.1308 0.1138 0.0595 0.068 Uiso calc R 1 . . C C17 0.3457(4) 0.2745(2) 0.17186(19) 0.0454(6) Uani d . 1 . . C C18 1.1267(5) 0.3485(2) 0.4488(2) 0.0577(7) Uani d . 1 . . H H18 1.0853 0.4236 0.4352 0.069 Uiso calc R 1 . . C C19 1.3349(5) 0.3437(2) 0.5238(2) 0.0622(7) Uani d . 1 . . H H19 1.4323 0.4154 0.5597 0.075 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0627(4) 0.0385(4) 0.0915(5) 0.0047(3) 0.0082(3) 0.0173(3) O1 0.0856(13) 0.0622(13) 0.0760(14) 0.0160(11) -0.0113(10) 0.0119(11) N1 0.0520(11) 0.0366(12) 0.0502(12) 0.0041(9) 0.0079(9) 0.0065(9) N2 0.0500(11) 0.0356(11) 0.0522(13) 0.0006(9) 0.0104(10) 0.0068(9) N3 0.0521(12) 0.0428(13) 0.0605(14) -0.0002(10) 0.0048(10) 0.0076(10) C1 0.0526(14) 0.0369(14) 0.0563(16) 0.0061(11) 0.0158(12) 0.0090(12) C2 0.0459(14) 0.0456(16) 0.084(2) -0.0024(12) 0.0038(13) 0.0178(14) C3 0.0442(13) 0.0470(16) 0.0749(19) 0.0022(12) 0.0009(12) 0.0191(14) C4 0.0462(13) 0.0373(13) 0.0474(14) 0.0050(11) 0.0114(11) 0.0045(11) C5 0.0450(13) 0.0359(13) 0.0476(15) 0.0029(10) 0.0141(11) 0.0033(11) C6 0.0523(14) 0.0343(13) 0.0473(14) 0.0031(11) 0.0126(11) 0.0055(11) C7 0.0526(13) 0.0379(14) 0.0445(14) 0.0031(11) 0.0117(11) 0.0078(11) C8 0.0589(14) 0.0363(14) 0.0583(16) 0.0008(11) 0.0075(12) 0.0064(12) C9 0.0610(15) 0.0399(15) 0.0571(16) 0.0070(12) 0.0091(13) 0.0113(12) C10 0.0617(15) 0.0440(15) 0.0449(15) 0.0055(12) 0.0064(12) 0.0087(12) C11 0.0725(17) 0.0542(17) 0.0537(17) 0.0018(14) -0.0025(13) 0.0078(14) C12 0.0497(14) 0.0411(14) 0.0667(17) 0.0070(12) 0.0007(12) 0.0075(13) C13 0.0466(14) 0.0378(14) 0.0656(17) -0.0014(11) 0.0033(12) 0.0048(12) C14 0.0530(14) 0.0400(14) 0.0515(15) 0.0069(12) 0.0103(12) 0.0099(12) C15 0.0535(14) 0.0384(14) 0.0633(17) -0.0060(12) 0.0051(12) 0.0040(12) C16 0.0541(14) 0.0450(16) 0.0636(17) -0.0055(12) 0.0047(12) 0.0034(13) C17 0.0516(14) 0.0360(14) 0.0497(15) 0.0052(11) 0.0137(11) 0.0067(11) C18 0.0718(17) 0.0367(14) 0.0601(17) 0.0069(13) -0.0016(14) 0.0071(13) C19 0.0759(18) 0.0417(15) 0.0582(17) -0.0047(13) -0.0065(14) 0.0029(13) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C1 . 1.736(2) ? O1 C11 . 1.200(3) ? N1 C5 . 1.321(3) ? N1 C6 . 1.376(3) ? N2 C15 . 1.367(3) ? N2 C14 . 1.369(3) ? N2 C17 . 1.391(3) ? N3 C17 . 1.333(3) ? N3 C16 . 1.359(3) ? C1 C12 . 1.373(3) ? C1 C2 . 1.380(3) ? C2 C3 . 1.379(3) ? C2 H2 . 0.93 ? C3 C4 . 1.390(3) ? C3 H3 . 0.93 ? C4 C13 . 1.394(3) ? C4 C5 . 1.474(3) ? C5 C17 . 1.422(3) ? C6 C14 . 1.345(3) ? C6 C7 . 1.485(3) ? C7 C18 . 1.382(3) ? C7 C8 . 1.398(3) ? C8 C9 . 1.377(3) ? C8 H8 . 0.93 ? C9 C10 . 1.379(3) ? C9 H9 . 0.93 ? C10 C19 . 1.379(3) ? C10 C11 . 1.478(3) ? C11 H11 . 0.93 ? C12 C13 . 1.384(3) ? C12 H12 . 0.93 ? C13 H13 . 0.93 ? C14 H14 . 0.93 ? C15 C16 . 1.359(3) ? C15 H15 . 0.93 ? C16 H16 . 0.93 ? C18 C19 . 1.384(3) ? C18 H18 . 0.93 ? C19 H19 . 0.93 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 N1 C6 . . 120.4(2) ? C15 N2 C14 . . 130.7(2) ? C15 N2 C17 . . 107.42(19) ? C14 N2 C17 . . 121.8(2) ? C17 N3 C16 . . 104.86(19) ? C12 C1 C2 . . 121.1(2) ? C12 C1 Cl1 . . 120.30(17) ? C2 C1 Cl1 . . 118.64(19) ? C1 C2 C3 . . 118.7(2) ? C1 C2 H2 . . 120.7 ? C3 C2 H2 . . 120.7 ? C2 C3 C4 . . 122.1(2) ? C2 C3 H3 . . 118.9 ? C4 C3 H3 . . 118.9 ? C3 C4 C13 . . 117.5(2) ? C3 C4 C5 . . 118.69(19) ? C13 C4 C5 . . 123.8(2) ? N1 C5 C17 . . 120.3(2) ? N1 C5 C4 . . 116.7(2) ? C17 C5 C4 . . 123.0(2) ? C14 C6 N1 . . 122.4(2) ? C14 C6 C7 . . 122.0(2) ? N1 C6 C7 . . 115.6(2) ? C18 C7 C8 . . 118.0(2) ? C18 C7 C6 . . 121.0(2) ? C8 C7 C6 . . 120.9(2) ? C9 C8 C7 . . 120.8(2) ? C9 C8 H8 . . 119.6 ? C7 C8 H8 . . 119.6 ? C8 C9 C10 . . 120.6(2) ? C8 C9 H9 . . 119.7 ? C10 C9 H9 . . 119.7 ? C19 C10 C9 . . 119.1(2) ? C19 C10 C11 . . 120.2(2) ? C9 C10 C11 . . 120.6(2) ? O1 C11 C10 . . 125.2(3) ? O1 C11 H11 . . 117.4 ? C10 C11 H11 . . 117.4 ? C1 C12 C13 . . 119.5(2) ? C1 C12 H12 . . 120.2 ? C13 C12 H12 . . 120.2 ? C12 C13 C4 . . 121.1(2) ? C12 C13 H13 . . 119.5 ? C4 C13 H13 . . 119.5 ? C6 C14 N2 . . 118.0(2) ? C6 C14 H14 . . 121.0 ? N2 C14 H14 . . 121.0 ? C16 C15 N2 . . 105.0(2) ? C16 C15 H15 . . 127.5 ? N2 C15 H15 . . 127.5 ? C15 C16 N3 . . 112.6(2) ? C15 C16 H16 . . 123.7 ? N3 C16 H16 . . 123.7 ? N3 C17 N2 . . 110.2(2) ? N3 C17 C5 . . 132.7(2) ? N2 C17 C5 . . 117.1(2) ? C19 C18 C7 . . 121.0(2) ? C19 C18 H18 . . 119.5 ? C7 C18 H18 . . 119.5 ? C10 C19 C18 . . 120.5(2) ? C10 C19 H19 . . 119.8 ? C18 C19 H19 . . 119.8 ? _database_code_depnum_ccdc_archive 'CCDC 960039'