# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_hxm #TrackingRef 'web_deposit_cif_file_0_Xiao-MeiHuang_1337496692.hxm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 N4 O2' _chemical_formula_weight 326.40 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 ? _symmetry_space_group_name_H-M ? 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 10.4376(18) _cell_length_b 8.2222(14) _cell_length_c 20.993(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.658(2) _cell_angle_gamma 90.00 _cell_volume 1795.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10842 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.52 _reflns_number_total 4120 _reflns_number_gt 2824 _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^)+(0.0823P)^2^+0.3343P] 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 SHELXL _refine_ls_extinction_coef 0.031(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4120 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1700 _refine_ls_wR_factor_gt 0.1519 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 1.62516(12) 0.55783(17) 0.36845(6) 0.0424(3) Uani 1 1 d . . . N2 N 1.43803(13) 0.71682(16) 0.36774(7) 0.0460(4) Uani 1 1 d . . . O2 O 1.57334(14) 0.67799(18) 0.45977(6) 0.0658(4) Uani 1 1 d . . . O1 O 1.22171(13) 0.6864(2) 0.34962(8) 0.0766(5) Uani 1 1 d . . . N21 N 1.54026(16) 0.4012(2) 0.28277(8) 0.0635(5) Uani 1 1 d . . . C11 C 1.73633(15) 0.4760(2) 0.39857(7) 0.0417(4) Uani 1 1 d . . . C14 C 1.95386(17) 0.3151(2) 0.45308(9) 0.0532(5) Uani 1 1 d . . . N22 N 1.6539(2) 0.6422(2) 0.26417(8) 0.0747(5) Uani 1 1 d . . . C21 C 1.60180(15) 0.5340(2) 0.30075(8) 0.0436(4) Uani 1 1 d . . . C1 C 1.55008(16) 0.6516(2) 0.40364(8) 0.0440(4) Uani 1 1 d . . . C6 C 1.33553(18) 0.4558(2) 0.39029(10) 0.0584(5) Uani 1 1 d . . . H6A H 1.4238 0.4300 0.4025 0.088 Uiso 1 1 calc R . . H6B H 1.3033 0.3842 0.3566 0.088 Uiso 1 1 calc R . . H6C H 1.2857 0.4425 0.4264 0.088 Uiso 1 1 calc R . . C2 C 1.4361(2) 0.8987(2) 0.35592(11) 0.0673(6) Uani 1 1 d . . . C13 C 1.83259(18) 0.2807(2) 0.47140(9) 0.0558(5) Uani 1 1 d . . . H13 H 1.8237 0.2022 0.5026 0.067 Uiso 1 1 calc R . . C12 C 1.72382(17) 0.3596(2) 0.44469(8) 0.0512(4) Uani 1 1 d . . . H12 H 1.6432 0.3340 0.4578 0.061 Uiso 1 1 calc R . . C7 C 1.32578(17) 0.6286(2) 0.36739(8) 0.0505(4) Uani 1 1 d . . . C16 C 1.85603(18) 0.5130(2) 0.37962(10) 0.0595(5) Uani 1 1 d . . . H16 H 1.8647 0.5918 0.3485 0.071 Uiso 1 1 calc R . . C15 C 1.96339(18) 0.4331(3) 0.40684(11) 0.0664(6) Uani 1 1 d . . . H15 H 2.0438 0.4593 0.3937 0.080 Uiso 1 1 calc R . . C17 C 2.0712(2) 0.2265(3) 0.48213(12) 0.0753(6) Uani 1 1 d . . . H17A H 2.0459 0.1496 0.5132 0.113 Uiso 1 1 calc R . . H17B H 2.1303 0.3035 0.5025 0.113 Uiso 1 1 calc R . . H17C H 2.1119 0.1702 0.4492 0.113 Uiso 1 1 calc R . . C3 C 1.5737(3) 0.9625(3) 0.36266(15) 0.0903(8) Uani 1 1 d . . . H3A H 1.6228 0.9102 0.3318 0.136 Uiso 1 1 calc R . . H3B H 1.6117 0.9397 0.4049 0.136 Uiso 1 1 calc R . . H3C H 1.5733 1.0779 0.3555 0.136 Uiso 1 1 calc R . . C22 C 1.5217(2) 0.3794(3) 0.21951(11) 0.0778(7) Uani 1 1 d . . . H22 H 1.4761 0.2885 0.2041 0.093 Uiso 1 1 calc R . . C23 C 1.5668(3) 0.4849(4) 0.17712(10) 0.0823(7) Uani 1 1 d . . . H23 H 1.5508 0.4700 0.1333 0.099 Uiso 1 1 calc R . . C24 C 1.6364(3) 0.6135(3) 0.20151(11) 0.0919(8) Uani 1 1 d . . . H24 H 1.6732 0.6840 0.1735 0.110 Uiso 1 1 calc R . . C5 C 1.3584(3) 0.9813(3) 0.40538(17) 0.1081(11) Uani 1 1 d . . . H5A H 1.2715 0.9421 0.4008 0.162 Uiso 1 1 calc R . . H5B H 1.3588 1.0968 0.3988 0.162 Uiso 1 1 calc R . . H5C H 1.3960 0.9567 0.4475 0.162 Uiso 1 1 calc R . . C4 C 1.3790(3) 0.9294(4) 0.28804(14) 0.1070(10) Uani 1 1 d . . . H4A H 1.4310 0.8769 0.2584 0.161 Uiso 1 1 calc R . . H4B H 1.3767 1.0442 0.2798 0.161 Uiso 1 1 calc R . . H4C H 1.2933 0.8863 0.2830 0.161 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 0.0405(7) 0.0465(8) 0.0400(7) -0.0016(6) 0.0013(5) 0.0033(6) N2 0.0453(8) 0.0399(8) 0.0530(8) 0.0078(6) 0.0055(6) 0.0056(6) O2 0.0738(9) 0.0770(10) 0.0458(7) -0.0120(6) -0.0008(6) 0.0202(7) O1 0.0454(8) 0.0836(11) 0.0993(11) 0.0234(9) -0.0033(7) 0.0133(7) N21 0.0661(10) 0.0711(11) 0.0535(9) -0.0145(8) 0.0062(7) -0.0195(8) C11 0.0377(8) 0.0438(9) 0.0430(8) -0.0050(7) 0.0004(6) 0.0009(7) C14 0.0437(10) 0.0570(11) 0.0572(11) -0.0048(9) -0.0051(8) 0.0032(8) N22 0.1085(15) 0.0658(11) 0.0509(10) 0.0057(8) 0.0126(9) -0.0139(10) C21 0.0415(9) 0.0469(9) 0.0424(9) -0.0008(7) 0.0036(6) 0.0049(7) C1 0.0444(9) 0.0421(9) 0.0458(9) 0.0010(7) 0.0048(7) 0.0013(7) C6 0.0492(10) 0.0531(11) 0.0737(13) 0.0092(9) 0.0093(9) -0.0040(8) C2 0.0724(13) 0.0418(11) 0.0894(15) 0.0165(10) 0.0180(11) 0.0090(9) C13 0.0534(11) 0.0615(12) 0.0521(10) 0.0104(9) 0.0025(8) 0.0066(9) C12 0.0428(9) 0.0604(11) 0.0513(10) 0.0082(8) 0.0079(7) 0.0005(8) C7 0.0453(10) 0.0553(11) 0.0513(10) 0.0078(8) 0.0054(7) 0.0058(8) C16 0.0455(10) 0.0603(12) 0.0732(12) 0.0168(10) 0.0079(8) -0.0030(8) C15 0.0362(9) 0.0742(14) 0.0893(15) 0.0116(11) 0.0081(9) -0.0015(9) C17 0.0541(12) 0.0795(15) 0.0899(16) 0.0027(12) -0.0101(11) 0.0120(11) C3 0.0930(18) 0.0494(13) 0.131(2) 0.0085(13) 0.0226(16) -0.0139(12) C22 0.0700(14) 0.0966(18) 0.0661(14) -0.0293(13) 0.0014(10) -0.0142(13) C23 0.0992(18) 0.106(2) 0.0405(11) -0.0085(12) -0.0033(11) 0.0172(15) C24 0.140(2) 0.0868(18) 0.0509(13) 0.0115(12) 0.0192(14) -0.0014(17) C5 0.124(2) 0.0476(13) 0.160(3) -0.0028(15) 0.058(2) 0.0190(14) C4 0.110(2) 0.095(2) 0.116(2) 0.0662(18) 0.0083(17) 0.0155(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 N1 C1 1.359(2) . ? N1 C21 1.436(2) . ? N1 C11 1.442(2) . ? N2 C7 1.377(2) . ? N2 C1 1.442(2) . ? N2 C2 1.516(2) . ? O2 C1 1.203(2) . ? O1 C7 1.216(2) . ? N21 C21 1.307(2) . ? N21 C22 1.338(3) . ? C11 C12 1.375(2) . ? C11 C16 1.376(2) . ? C14 C15 1.382(3) . ? C14 C13 1.382(3) . ? C14 C17 1.510(3) . ? N22 C21 1.321(2) . ? N22 C24 1.334(3) . ? C6 C7 1.501(3) . ? C2 C4 1.520(4) . ? C2 C3 1.525(3) . ? C2 C5 1.528(3) . ? C13 C12 1.386(3) . ? C16 C15 1.382(3) . ? C22 C23 1.354(4) . ? C23 C24 1.359(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 C1 N1 C21 123.81(13) . . ? C1 N1 C11 120.34(13) . . ? C21 N1 C11 115.85(13) . . ? C7 N2 C1 117.40(14) . . ? C7 N2 C2 121.26(15) . . ? C1 N2 C2 116.85(15) . . ? C21 N21 C22 115.24(18) . . ? C12 C11 C16 119.85(16) . . ? C12 C11 N1 120.96(15) . . ? C16 C11 N1 119.17(15) . . ? C15 C14 C13 117.34(16) . . ? C15 C14 C17 121.33(18) . . ? C13 C14 C17 121.33(18) . . ? C21 N22 C24 115.1(2) . . ? N21 C21 N22 127.64(16) . . ? N21 C21 N1 116.11(15) . . ? N22 C21 N1 116.02(15) . . ? O2 C1 N1 123.71(15) . . ? O2 C1 N2 122.36(15) . . ? N1 C1 N2 113.93(14) . . ? N2 C2 C4 108.4(2) . . ? N2 C2 C3 108.95(17) . . ? C4 C2 C3 108.9(2) . . ? N2 C2 C5 109.13(17) . . ? C4 C2 C5 112.0(2) . . ? C3 C2 C5 109.4(2) . . ? C14 C13 C12 122.04(17) . . ? C11 C12 C13 119.28(16) . . ? O1 C7 N2 122.28(17) . . ? O1 C7 C6 120.24(17) . . ? N2 C7 C6 117.47(15) . . ? C11 C16 C15 120.02(18) . . ? C14 C15 C16 121.47(18) . . ? N21 C22 C23 122.4(2) . . ? C22 C23 C24 117.0(2) . . ? N22 C24 C23 122.3(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.289 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 882910' ####################################################################### # # 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_hxm-2-207-1 #TrackingRef 'web_deposit_cif_file_0_Xiao-MeiHuang_1337687662.hxm-2-207-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 Cl2 N4 O2' _chemical_formula_weight 429.29 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 15.245(5) _cell_length_b 8.417(5) _cell_length_c 16.508(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 104.637(5) _cell_angle_gamma 90.000(5) _cell_volume 2049.5(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.342 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12314 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 27.56 _reflns_number_total 4697 _reflns_number_gt 3485 _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^)+(0.0657P)^2^+0.4440P] 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 4697 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1278 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _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 Cl22 Cl 0.16456(4) 0.63016(6) 0.50535(4) 0.05573(17) Uani 1 1 d . . . Cl21 Cl 0.16663(4) 0.01014(6) 0.41952(4) 0.06225(18) Uani 1 1 d . . . O2 O 0.33881(8) 0.27441(17) 0.48977(8) 0.0457(3) Uani 1 1 d . . . C5 C 0.33031(18) 0.2345(4) 0.20256(15) 0.0783(8) Uani 1 1 d . . . H5A H 0.3927 0.2604 0.2271 0.117 Uiso 1 1 calc R . . H5B H 0.3041 0.3129 0.1613 0.117 Uiso 1 1 calc R . . H5C H 0.3266 0.1320 0.1764 0.117 Uiso 1 1 calc R . . N2 N 0.33233(9) 0.26745(17) 0.35111(9) 0.0360(3) Uani 1 1 d . . . N1 N 0.20698(9) 0.35705(17) 0.40331(9) 0.0355(3) Uani 1 1 d . . . O1 O 0.20080(10) 0.2016(2) 0.25471(9) 0.0627(4) Uani 1 1 d . . . N32 N 0.07505(10) 0.4640(2) 0.31929(10) 0.0441(4) Uani 1 1 d . . . C2 C 0.29601(11) 0.2988(2) 0.41923(11) 0.0340(4) Uani 1 1 d . . . N31 N 0.21942(11) 0.5473(2) 0.30441(12) 0.0531(4) Uani 1 1 d . . . C31 C 0.16508(12) 0.4607(2) 0.33760(11) 0.0382(4) Uani 1 1 d . . . C11 C 0.42932(12) 0.2354(2) 0.37208(11) 0.0387(4) Uani 1 1 d . . . C12 C 0.45779(14) 0.0776(2) 0.38015(14) 0.0512(5) Uani 1 1 d . . . C21 C 0.15932(11) 0.3185(2) 0.46479(11) 0.0365(4) Uani 1 1 d . . . C16 C 0.49006(13) 0.3616(2) 0.38347(13) 0.0458(4) Uani 1 1 d . . . C22 C 0.13731(12) 0.1621(2) 0.47842(12) 0.0431(4) Uani 1 1 d . . . C24 C 0.06541(14) 0.2414(3) 0.58440(14) 0.0589(6) Uani 1 1 d . . . H24 H 0.0331 0.2159 0.6235 0.071 Uiso 1 1 calc R . . C25 C 0.08608(13) 0.3970(3) 0.57275(13) 0.0529(5) Uani 1 1 d . . . H25 H 0.0677 0.4769 0.6037 0.063 Uiso 1 1 calc R . . C26 C 0.13427(12) 0.4343(2) 0.51489(11) 0.0400(4) Uani 1 1 d . . . C13 C 0.55100(17) 0.0491(3) 0.40047(16) 0.0664(7) Uani 1 1 d . . . H13 H 0.5721 -0.0550 0.4071 0.080 Uiso 1 1 calc R . . C32 C 0.03622(14) 0.5684(3) 0.25973(12) 0.0530(5) Uani 1 1 d . . . H32 H -0.0266 0.5777 0.2452 0.064 Uiso 1 1 calc R . . C15 C 0.58195(14) 0.3267(3) 0.40254(16) 0.0610(6) Uani 1 1 d . . . H15 H 0.6240 0.4089 0.4098 0.073 Uiso 1 1 calc R . . C18 C 0.45855(16) 0.5314(3) 0.37550(18) 0.0639(6) Uani 1 1 d . . . H18A H 0.3935 0.5343 0.3621 0.096 Uiso 1 1 calc R . . H18B H 0.4794 0.5826 0.3318 0.096 Uiso 1 1 calc R . . H18C H 0.4826 0.5857 0.4275 0.096 Uiso 1 1 calc R . . C17 C 0.39248(19) -0.0587(3) 0.3687(2) 0.0762(8) Uani 1 1 d . . . H17A H 0.4255 -0.1570 0.3768 0.114 Uiso 1 1 calc R . . H17B H 0.3533 -0.0558 0.3132 0.114 Uiso 1 1 calc R . . H17C H 0.3568 -0.0508 0.4089 0.114 Uiso 1 1 calc R . . C23 C 0.09216(14) 0.1234(3) 0.53861(13) 0.0539(5) Uani 1 1 d . . . H23 H 0.0800 0.0177 0.5480 0.065 Uiso 1 1 calc R . . C4 C 0.27979(14) 0.2316(3) 0.26896(12) 0.0476(5) Uani 1 1 d . . . C14 C 0.61163(15) 0.1709(3) 0.41081(17) 0.0695(7) Uani 1 1 d . . . H14 H 0.6734 0.1491 0.4235 0.083 Uiso 1 1 calc R . . C33 C 0.08506(17) 0.6617(3) 0.21964(15) 0.0634(6) Uani 1 1 d . . . H33 H 0.0571 0.7323 0.1777 0.076 Uiso 1 1 calc R . . C34 C 0.17725(17) 0.6462(3) 0.24408(16) 0.0645(6) Uani 1 1 d . . . H34 H 0.2122 0.7077 0.2173 0.077 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 Cl22 0.0556(3) 0.0434(3) 0.0687(4) -0.0069(2) 0.0168(2) -0.0021(2) Cl21 0.0782(4) 0.0389(3) 0.0690(4) -0.0001(2) 0.0175(3) -0.0066(2) O2 0.0399(7) 0.0576(9) 0.0365(7) 0.0035(6) 0.0040(5) 0.0082(6) C5 0.0714(16) 0.122(2) 0.0442(13) -0.0090(14) 0.0201(11) -0.0009(16) N2 0.0328(7) 0.0368(8) 0.0375(8) 0.0005(6) 0.0070(6) 0.0023(6) N1 0.0310(7) 0.0382(8) 0.0374(8) 0.0077(6) 0.0086(6) 0.0042(6) O1 0.0477(8) 0.0891(12) 0.0454(8) -0.0114(8) 0.0010(6) -0.0085(8) N32 0.0349(8) 0.0543(10) 0.0407(8) 0.0055(7) 0.0049(6) 0.0053(7) C2 0.0341(8) 0.0294(8) 0.0376(9) 0.0020(7) 0.0070(7) -0.0004(7) N31 0.0454(9) 0.0508(10) 0.0652(11) 0.0239(9) 0.0178(8) 0.0077(8) C31 0.0374(9) 0.0384(10) 0.0385(9) 0.0046(7) 0.0091(7) 0.0052(7) C11 0.0357(9) 0.0395(10) 0.0412(10) 0.0012(8) 0.0102(7) 0.0076(7) C12 0.0545(12) 0.0402(11) 0.0609(13) 0.0004(9) 0.0184(10) 0.0102(9) C21 0.0280(8) 0.0425(10) 0.0367(9) 0.0073(7) 0.0039(6) -0.0015(7) C16 0.0395(10) 0.0436(11) 0.0546(11) 0.0016(9) 0.0123(8) 0.0043(8) C22 0.0384(9) 0.0444(10) 0.0424(10) 0.0062(8) 0.0029(7) -0.0050(8) C24 0.0463(11) 0.0838(17) 0.0482(12) 0.0139(12) 0.0149(9) -0.0082(11) C25 0.0424(11) 0.0726(15) 0.0447(11) -0.0004(10) 0.0129(8) 0.0024(10) C26 0.0306(8) 0.0458(10) 0.0408(9) 0.0024(8) 0.0035(7) 0.0000(7) C13 0.0635(15) 0.0558(14) 0.0810(17) 0.0061(12) 0.0201(12) 0.0295(12) C32 0.0431(11) 0.0677(14) 0.0442(11) 0.0051(10) 0.0037(8) 0.0179(10) C15 0.0386(10) 0.0654(15) 0.0788(16) 0.0016(12) 0.0142(10) 0.0019(10) C18 0.0505(12) 0.0400(11) 0.1000(19) 0.0010(12) 0.0169(12) -0.0029(9) C17 0.0812(17) 0.0354(12) 0.113(2) 0.0002(13) 0.0258(16) 0.0060(11) C23 0.0473(11) 0.0600(14) 0.0505(12) 0.0160(10) 0.0053(9) -0.0159(10) C4 0.0511(11) 0.0490(12) 0.0407(10) -0.0020(9) 0.0079(8) 0.0052(9) C14 0.0418(12) 0.0800(18) 0.0866(18) 0.0057(14) 0.0161(11) 0.0198(12) C33 0.0717(15) 0.0620(14) 0.0548(13) 0.0226(11) 0.0132(11) 0.0269(12) C34 0.0669(14) 0.0585(14) 0.0728(15) 0.0321(12) 0.0263(12) 0.0133(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 Cl22 C26 1.730(2) . ? Cl21 C22 1.732(2) . ? O2 C2 1.200(2) . ? C5 C4 1.491(3) . ? N2 C2 1.398(2) . ? N2 C4 1.422(2) . ? N2 C11 1.456(2) . ? N1 C2 1.404(2) . ? N1 C31 1.413(2) . ? N1 C21 1.427(2) . ? O1 C4 1.194(2) . ? N32 C31 1.329(2) . ? N32 C32 1.340(3) . ? N31 C31 1.322(2) . ? N31 C34 1.332(3) . ? C11 C16 1.391(3) . ? C11 C12 1.393(3) . ? C12 C13 1.396(3) . ? C12 C17 1.500(3) . ? C21 C22 1.391(3) . ? C21 C26 1.393(3) . ? C16 C15 1.388(3) . ? C16 C18 1.503(3) . ? C22 C23 1.383(3) . ? C24 C23 1.371(3) . ? C24 C25 1.371(3) . ? C25 C26 1.381(3) . ? C13 C14 1.362(4) . ? C32 C33 1.363(3) . ? C15 C14 1.382(4) . ? C33 C34 1.367(3) . ? 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 N2 C4 124.39(15) . . ? C2 N2 C11 115.36(14) . . ? C4 N2 C11 118.74(15) . . ? C2 N1 C31 125.99(14) . . ? C2 N1 C21 115.42(13) . . ? C31 N1 C21 118.29(14) . . ? C31 N32 C32 114.83(17) . . ? O2 C2 N2 121.30(15) . . ? O2 C2 N1 120.28(16) . . ? N2 C2 N1 118.41(14) . . ? C31 N31 C34 114.82(18) . . ? N31 C31 N32 127.85(17) . . ? N31 C31 N1 116.72(16) . . ? N32 C31 N1 115.35(15) . . ? C16 C11 C12 122.32(17) . . ? C16 C11 N2 119.47(16) . . ? C12 C11 N2 118.20(17) . . ? C11 C12 C13 117.4(2) . . ? C11 C12 C17 122.5(2) . . ? C13 C12 C17 120.1(2) . . ? C22 C21 C26 116.93(17) . . ? C22 C21 N1 121.16(17) . . ? C26 C21 N1 121.90(16) . . ? C15 C16 C11 117.94(19) . . ? C15 C16 C18 120.2(2) . . ? C11 C16 C18 121.84(17) . . ? C23 C22 C21 121.56(19) . . ? C23 C22 Cl21 118.37(17) . . ? C21 C22 Cl21 120.07(15) . . ? C23 C24 C25 120.2(2) . . ? C24 C25 C26 119.7(2) . . ? C25 C26 C21 121.66(19) . . ? C25 C26 Cl22 118.77(16) . . ? C21 C26 Cl22 119.57(14) . . ? C14 C13 C12 121.2(2) . . ? N32 C32 C33 122.67(19) . . ? C14 C15 C16 120.7(2) . . ? C24 C23 C22 119.8(2) . . ? O1 C4 N2 121.98(18) . . ? O1 C4 C5 122.77(19) . . ? N2 C4 C5 115.25(18) . . ? C13 C14 C15 120.4(2) . . ? C32 C33 C34 116.7(2) . . ? N31 C34 C33 123.1(2) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.303 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 883162' ####################################################################### # # 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_hxm52 #TrackingRef 'web_deposit_cif_file_0_Xiao-MeiHuang_1340601995.hxm52.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H22 N4 O2' _chemical_formula_weight 338.41 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 ? _symmetry_space_group_name_H-M ? 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 10.47(2) _cell_length_b 13.29(3) _cell_length_c 14.71(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.91(3) _cell_angle_gamma 90.00 _cell_volume 1969(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8416 _diffrn_reflns_av_R_equivalents 0.0637 _diffrn_reflns_av_sigmaI/netI 0.0825 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3226 _reflns_number_gt 1382 _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^)+(0.2000P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.14(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3226 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2259 _refine_ls_R_factor_gt 0.1526 _refine_ls_wR_factor_ref 0.4040 _refine_ls_wR_factor_gt 0.3146 _refine_ls_goodness_of_fit_ref 1.223 _refine_ls_restrained_S_all 1.223 _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 C1 C 0.6102(5) 0.7476(4) 0.2888(3) 0.0510(14) Uani 1 1 d . . . C2 C 0.7821(5) 0.8282(4) 0.4309(3) 0.0607(16) Uani 1 1 d . . . C3 C 0.8434(7) 0.7636(4) 0.2832(3) 0.0653(17) Uani 1 1 d . . . C4 C 0.7939(6) 0.7202(4) 0.1853(3) 0.0645(17) Uani 1 1 d . . . H4 H 0.7140 0.6851 0.1693 0.077 Uiso 1 1 calc R . . C5 C 0.8609(6) 0.7306(5) 0.1214(3) 0.0728(18) Uani 1 1 d . . . H5 H 0.9408 0.7655 0.1397 0.087 Uiso 1 1 calc R . . C6 C 0.8187(7) 0.6907(6) 0.0209(4) 0.091(2) Uani 1 1 d . . . H6A H 0.8846 0.7080 -0.0108 0.137 Uiso 1 1 calc R . . H6B H 0.7351 0.7199 -0.0122 0.137 Uiso 1 1 calc R . . H6C H 0.8099 0.6188 0.0221 0.137 Uiso 1 1 calc R . . C7 C 0.6551(7) 0.8299(6) 0.4676(4) 0.085(2) Uani 1 1 d . . . H7A H 0.6293 0.7622 0.4769 0.128 Uiso 1 1 calc R . . H7B H 0.5841 0.8629 0.4220 0.128 Uiso 1 1 calc R . . H7C H 0.6740 0.8657 0.5265 0.128 Uiso 1 1 calc R . . C8 C 0.8212(8) 0.9386(6) 0.4164(4) 0.102(3) Uani 1 1 d . . . H8A H 0.8988 0.9389 0.3936 0.152 Uiso 1 1 calc R . . H8B H 0.8398 0.9739 0.4755 0.152 Uiso 1 1 calc R . . H8C H 0.7493 0.9710 0.3711 0.152 Uiso 1 1 calc R . . C9 C 0.8942(7) 0.7702(6) 0.5045(4) 0.098(2) Uani 1 1 d . . . H9A H 0.8554 0.7300 0.5442 0.146 Uiso 1 1 calc R . . H9B H 0.9551 0.8175 0.5426 0.146 Uiso 1 1 calc R . . H9C H 0.9408 0.7274 0.4718 0.146 Uiso 1 1 calc R . . C11 C 0.4316(5) 0.6188(4) 0.2749(3) 0.0533(14) Uani 1 1 d . . . C12 C 0.3276(6) 0.6805(5) 0.2826(3) 0.0623(16) Uani 1 1 d . . . H12 H 0.3448 0.7460 0.3049 0.075 Uiso 1 1 calc R . . C13 C 0.1957(6) 0.6436(7) 0.2566(4) 0.088(2) Uani 1 1 d . . . H13 H 0.1266 0.6847 0.2625 0.106 Uiso 1 1 calc R . . C14 C 0.1690(8) 0.5460(7) 0.2223(4) 0.092(2) Uani 1 1 d . . . H14 H 0.0823 0.5218 0.2053 0.110 Uiso 1 1 calc R . . C15 C 0.2736(8) 0.4848(7) 0.2136(4) 0.092(2) Uani 1 1 d . . . H15 H 0.2561 0.4198 0.1900 0.111 Uiso 1 1 calc R . . C16 C 0.4038(7) 0.5203(5) 0.2400(3) 0.0760(19) Uani 1 1 d . . . H16 H 0.4727 0.4787 0.2345 0.091 Uiso 1 1 calc R . . C21 C 0.6626(5) 0.5816(4) 0.3710(3) 0.0545(15) Uani 1 1 d . . . C22 C 0.8389(6) 0.4751(5) 0.4025(4) 0.0743(18) Uani 1 1 d . . . H22 H 0.9110 0.4467 0.3865 0.089 Uiso 1 1 calc R . . C23 C 0.8148(7) 0.4486(5) 0.4890(4) 0.084(2) Uani 1 1 d . . . H23 H 0.8693 0.4035 0.5304 0.101 Uiso 1 1 calc R . . C24 C 0.7081(7) 0.4921(5) 0.5091(4) 0.079(2) Uani 1 1 d . . . H24 H 0.6907 0.4753 0.5659 0.095 Uiso 1 1 calc R . . N1 N 0.5698(4) 0.6510(3) 0.3080(2) 0.0553(13) Uani 1 1 d . . . N2 N 0.7496(4) 0.7715(4) 0.3361(2) 0.0593(14) Uani 1 1 d . . . N21 N 0.6245(5) 0.5593(4) 0.4508(3) 0.0716(16) Uani 1 1 d . . . N22 N 0.7600(5) 0.5410(4) 0.3416(3) 0.0637(14) Uani 1 1 d . . . O1 O 0.5357(4) 0.8092(3) 0.2379(2) 0.0702(13) Uani 1 1 d . . . O2 O 0.9576(4) 0.7937(4) 0.3154(3) 0.0821(15) 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 C1 0.060(3) 0.058(4) 0.031(2) 0.002(2) 0.006(2) -0.002(3) C2 0.074(4) 0.070(4) 0.037(2) -0.008(2) 0.012(2) -0.008(3) C3 0.090(5) 0.063(4) 0.039(2) 0.000(2) 0.012(3) 0.001(3) C4 0.085(4) 0.065(4) 0.044(3) -0.003(2) 0.019(3) 0.000(3) C5 0.075(4) 0.095(5) 0.051(3) 0.014(3) 0.020(3) 0.015(3) C6 0.128(6) 0.101(6) 0.055(3) 0.007(3) 0.043(3) 0.022(4) C7 0.111(5) 0.097(6) 0.047(3) -0.017(3) 0.022(3) 0.003(4) C8 0.144(7) 0.089(6) 0.070(4) -0.025(3) 0.026(4) -0.029(5) C9 0.099(5) 0.137(7) 0.043(3) -0.006(3) -0.004(3) 0.018(5) C11 0.062(3) 0.066(4) 0.0281(19) 0.002(2) 0.0066(19) -0.004(3) C12 0.074(4) 0.067(4) 0.042(2) 0.004(2) 0.010(2) 0.001(3) C13 0.072(5) 0.135(7) 0.052(3) 0.016(3) 0.006(3) 0.007(4) C14 0.080(5) 0.116(7) 0.064(4) 0.014(4) -0.005(3) -0.032(5) C15 0.101(6) 0.096(6) 0.067(4) -0.007(3) 0.001(3) -0.027(5) C16 0.097(5) 0.072(4) 0.051(3) -0.008(3) 0.007(3) -0.008(4) C21 0.060(4) 0.060(4) 0.041(2) 0.002(2) 0.011(2) 0.000(3) C22 0.073(4) 0.067(4) 0.075(4) -0.006(3) 0.008(3) 0.014(3) C23 0.089(5) 0.081(5) 0.066(3) 0.019(3) -0.006(3) 0.018(4) C24 0.094(5) 0.079(5) 0.059(3) 0.025(3) 0.012(3) 0.020(4) N1 0.060(3) 0.063(3) 0.0369(19) 0.0053(17) 0.0039(17) -0.002(2) N2 0.071(3) 0.073(3) 0.0313(18) -0.0034(17) 0.0089(18) 0.001(2) N21 0.082(4) 0.084(4) 0.051(2) 0.018(2) 0.022(2) 0.010(3) N22 0.073(3) 0.066(3) 0.049(2) -0.003(2) 0.011(2) 0.014(2) O1 0.072(3) 0.078(3) 0.053(2) 0.0192(18) 0.0044(17) 0.001(2) O2 0.063(3) 0.114(4) 0.068(2) -0.016(2) 0.0156(19) -0.020(2) _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 C1 O1 1.232(6) . ? C1 N1 1.404(7) . ? C1 N2 1.469(7) . ? C2 N2 1.539(6) . ? C2 C8 1.553(9) . ? C2 C9 1.565(8) . ? C2 C7 1.567(9) . ? C3 O2 1.227(7) . ? C3 N2 1.414(8) . ? C3 C4 1.504(7) . ? C4 C5 1.326(8) . ? C4 H4 0.9300 . ? C5 C6 1.518(8) . ? C5 H5 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? 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 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C11 C12 1.394(8) . ? C11 C16 1.408(8) . ? C11 N1 1.458(7) . ? C12 C13 1.415(9) . ? C12 H12 0.9300 . ? C13 C14 1.392(11) . ? C13 H13 0.9300 . ? C14 C15 1.399(11) . ? C14 H14 0.9300 . ? C15 C16 1.393(9) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C21 N22 1.326(7) . ? C21 N21 1.371(7) . ? C21 N1 1.471(7) . ? C22 N22 1.358(7) . ? C22 C23 1.408(9) . ? C22 H22 0.9300 . ? C23 C24 1.361(9) . ? C23 H23 0.9300 . ? C24 N21 1.374(7) . ? C24 H24 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 O1 C1 N1 123.7(5) . . ? O1 C1 N2 121.6(5) . . ? N1 C1 N2 114.7(4) . . ? N2 C2 C8 109.9(4) . . ? N2 C2 C9 108.8(5) . . ? C8 C2 C9 112.6(5) . . ? N2 C2 C7 108.8(4) . . ? C8 C2 C7 108.3(5) . . ? C9 C2 C7 108.4(5) . . ? O2 C3 N2 120.9(5) . . ? O2 C3 C4 122.6(5) . . ? N2 C3 C4 116.5(5) . . ? C5 C4 C3 121.9(6) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 125.8(6) . . ? C4 C5 H5 117.1 . . ? C6 C5 H5 117.1 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C9 H9A 109.5 . . ? C2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C12 C11 C16 119.3(5) . . ? C12 C11 N1 121.7(5) . . ? C16 C11 N1 118.9(5) . . ? C11 C12 C13 120.0(6) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 120.4(7) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 119.4(7) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 120.5(7) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C11 120.4(7) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? N22 C21 N21 128.4(5) . . ? N22 C21 N1 119.0(4) . . ? N21 C21 N1 112.2(5) . . ? N22 C22 C23 122.0(6) . . ? N22 C22 H22 119.0 . . ? C23 C22 H22 119.0 . . ? C24 C23 C22 116.8(5) . . ? C24 C23 H23 121.6 . . ? C22 C23 H23 121.6 . . ? C23 C24 N21 124.1(6) . . ? C23 C24 H24 117.9 . . ? N21 C24 H24 117.9 . . ? C1 N1 C11 121.8(4) . . ? C1 N1 C21 121.1(4) . . ? C11 N1 C21 116.7(4) . . ? C3 N2 C1 118.3(4) . . ? C3 N2 C2 121.4(4) . . ? C1 N2 C2 118.6(4) . . ? C21 N21 C24 112.9(5) . . ? C21 N22 C22 115.5(5) . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.927 _refine_diff_density_max 0.727 _refine_diff_density_min -0.652 _refine_diff_density_rms 0.204 _database_code_depnum_ccdc_archive 'CCDC 888379'