# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2018 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_a_a _database_code_depnum_ccdc_archive 'CCDC 1583075' _audit_update_record ; 2017-10-31 deposited with the CCDC. 2018-04-02 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H30 Br N3 O5' _chemical_formula_weight 604.49 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' Br Br -0.2901 2.4595 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0254(6) _cell_length_b 15.9496(9) _cell_length_c 16.7865(7) _cell_angle_alpha 90 _cell_angle_beta 115.616(3) _cell_angle_gamma 90 _cell_volume 2903.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9800 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 28.34 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_F_000 1248 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.338 _exptl_crystal_size_mid 0.284 _exptl_crystal_size_min 0.10 _exptl_absorpt_coefficient_mu 1.460 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.841 _exptl_absorpt_correction_T_max 0.887 _exptl_absorpt_process_details SADABS_Bruker_2014 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 95862 _diffrn_reflns_av_unetI/netI 0.0979 _diffrn_reflns_av_R_equivalents 0.1338 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.187 _diffrn_reflns_theta_max 33.833 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 11677 _reflns_number_gt 6536 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _computing_structure_refinement 'SHELXL-2014 (Sheldrick 2014)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1384P)^2^+5.4193P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 11677 _refine_ls_number_parameters 357 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1672 _refine_ls_R_factor_gt 0.0907 _refine_ls_wR_factor_ref 0.2789 _refine_ls_wR_factor_gt 0.2317 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.44192(4) -0.23413(3) 0.26318(3) 0.04130(16) Uani 1 1 d . . . . . O1 O -0.0876(4) -0.56517(19) 0.3904(2) 0.0526(11) Uani 1 1 d . . . . . O2 O -0.1449(2) -0.30620(14) 0.19161(14) 0.0171(4) Uani 1 1 d . . . . . N1 N -0.1023(3) -0.57831(16) 0.21141(18) 0.0203(5) Uani 1 1 d . . . . . N2 N -0.2849(5) -0.5130(2) 0.3142(3) 0.0444(10) Uani 1 1 d . . . . . H2B H -0.3112 -0.5197 0.3539 0.053 Uiso 1 1 calc R U . . . N3 N -0.1114(3) -0.3146(2) 0.47271(18) 0.0296(7) Uani 1 1 d . . . . . H2 H -0.0931 -0.3260 0.5180 0.036 Uiso 1 1 d R U . . . C1 C -0.1577(3) -0.50966(19) 0.2401(2) 0.0193(6) Uani 1 1 d . . . . . C2 C -0.0620(3) -0.43772(18) 0.25735(19) 0.0155(5) Uani 1 1 d . . . . . H2A H 0.0095 -0.4479 0.3139 0.019 Uiso 1 1 calc R U . . . C3 C -0.0232(3) -0.44886(18) 0.18175(19) 0.0148(5) Uani 1 1 d . . . . . H3A H -0.0895 -0.4269 0.1275 0.018 Uiso 1 1 calc R U . . . C4 C -0.0200(3) -0.5442(2) 0.1727(2) 0.0194(6) Uani 1 1 d . . . . . H4A H 0.0644 -0.5643 0.2075 0.023 Uiso 1 1 calc R U . . . C5 C -0.0694(4) -0.5809(2) 0.0797(2) 0.0244(7) Uani 1 1 d . . . . . H5A H -0.1306 -0.5444 0.0370 0.029 Uiso 1 1 calc R U . . . H5B H -0.0033 -0.5903 0.0622 0.029 Uiso 1 1 calc R U . . . C6 C -0.1267(4) -0.6635(2) 0.0888(2) 0.0274(7) Uani 1 1 d . . . . . H6A H -0.1881 -0.6827 0.0319 0.033 Uiso 1 1 calc R U . . . H6B H -0.0642 -0.7066 0.1143 0.033 Uiso 1 1 calc R U . . . C7 C -0.1856(4) -0.6421(2) 0.1504(3) 0.0270(7) Uani 1 1 d . . . . . H7A H -0.2679 -0.6195 0.1175 0.032 Uiso 1 1 calc R U . . . H7B H -0.1907 -0.6913 0.1826 0.032 Uiso 1 1 calc R U . . . C8 C -0.2892(3) -0.4801(2) 0.1811(3) 0.0235(7) Uani 1 1 d . . . . . C9 C -0.3424(3) -0.4487(2) 0.0965(3) 0.0269(7) Uani 1 1 d . . . . . H9A H -0.2993 -0.4501 0.0619 0.032 Uiso 1 1 calc R U . . . C10 C -0.4616(4) -0.4148(3) 0.0624(4) 0.0415(11) Uani 1 1 d . . . . . H10A H -0.4967 -0.3932 0.0054 0.050 Uiso 1 1 calc R U . . . C11 C -0.5264(4) -0.4130(3) 0.1113(4) 0.0471(12) Uani 1 1 d . . . . . H11A H -0.6049 -0.3896 0.0878 0.057 Uiso 1 1 calc R U . . . C12 C -0.4777(5) -0.4453(3) 0.1946(5) 0.0535(16) Uani 1 1 d . . . . . H12A H -0.5232 -0.4453 0.2274 0.064 Uiso 1 1 calc R U . . . C13 C -0.3560(4) -0.4791(2) 0.2307(3) 0.0359(10) Uani 1 1 d . . . . . C14 C -0.1699(5) -0.5340(2) 0.3254(3) 0.0366(10) Uani 1 1 d . . . . . C15 C -0.1127(3) -0.35055(18) 0.25869(18) 0.0147(5) Uani 1 1 d . . . . . C16 C -0.1254(3) -0.32223(19) 0.33548(18) 0.0174(6) Uani 1 1 d . . . . . C17 C -0.0798(4) -0.3599(2) 0.4181(2) 0.0273(8) Uani 1 1 d . . . . . H17A H -0.0341 -0.4092 0.4334 0.033 Uiso 1 1 calc R U . . . C18 C -0.1802(3) -0.2456(2) 0.4285(2) 0.0208(6) Uani 1 1 d . . . . . C19 C -0.2327(3) -0.1825(2) 0.4586(2) 0.0221(6) Uani 1 1 d . . . . . H19A H -0.2259 -0.1825 0.5159 0.027 Uiso 1 1 calc R U . . . C20 C -0.2956(3) -0.1197(2) 0.3990(2) 0.0219(6) Uani 1 1 d . . . . . H20A H -0.3307 -0.0761 0.4171 0.026 Uiso 1 1 calc R U . . . C21 C -0.3074(3) -0.1205(2) 0.3124(2) 0.0211(6) Uani 1 1 d . . . . . H21A H -0.3506 -0.0776 0.2740 0.025 Uiso 1 1 calc R U . . . C22 C -0.2563(3) -0.18385(19) 0.2828(2) 0.0168(6) Uani 1 1 d . . . . . H22A H -0.2654 -0.1839 0.2249 0.020 Uiso 1 1 calc R U . . . C23 C -0.1906(3) -0.24776(18) 0.3410(2) 0.0154(5) Uani 1 1 d . . . . . C24 C 0.0937(3) -0.4015(2) 0.1979(2) 0.0182(6) Uani 1 1 d . . . . . C25 C 0.0895(3) -0.3336(2) 0.1448(2) 0.0214(6) Uani 1 1 d . . . . . H25A H 0.0158 -0.3212 0.0962 0.026 Uiso 1 1 calc R U . . . C26 C 0.1924(4) -0.2837(2) 0.1623(3) 0.0273(7) Uani 1 1 d . . . . . H26A H 0.1875 -0.2379 0.1266 0.033 Uiso 1 1 calc R U . . . C27 C 0.3019(3) -0.3035(3) 0.2339(3) 0.0277(8) Uani 1 1 d . . . . . C28 C 0.3104(3) -0.3724(3) 0.2863(3) 0.0309(8) Uani 1 1 d . . . . . H28A H 0.3852 -0.3862 0.3332 0.037 Uiso 1 1 calc R U . . . C29 C 0.2060(3) -0.4212(2) 0.2683(3) 0.0271(7) Uani 1 1 d . . . . . H29A H 0.2114 -0.4673 0.3037 0.033 Uiso 1 1 calc R U . . . O3 O -0.3669(7) -0.3983(4) 0.5614(3) 0.0454(18) Uani 0.5 1 d . . P . . C30 C -0.4235(8) -0.3141(6) 0.5275(5) 0.038(2) Uani 0.5 1 d . . P . . H30A H -0.4269 -0.3047 0.4694 0.046 Uiso 0.5 1 calc R U P . . H30B H -0.3726 -0.2705 0.5667 0.046 Uiso 0.5 1 calc R U P . . C33 C -0.5575(11) -0.3092(8) 0.5219(8) 0.054(3) Uiso 0.5 1 d . . P . . H33A H -0.6104 -0.2795 0.4694 0.080 Uiso 0.5 1 calc R U P . . H33B H -0.5551 -0.2802 0.5728 0.080 Uiso 0.5 1 calc R U P . . H33C H -0.5888 -0.3649 0.5202 0.080 Uiso 0.5 1 calc R U P . . O1W O -0.1082(3) -0.15077(17) 0.13937(17) 0.0405(8) Uani 1 1 d . . . . . H1 H -0.1107 -0.1841 0.1749 0.061 Uiso 1 1 d R U . . . O2W O -0.4282(8) -0.5076(4) 0.4149(4) 0.123(3) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0234(2) 0.0517(3) 0.0479(3) -0.0149(2) 0.01459(19) -0.01497(17) O1 0.113(3) 0.0258(15) 0.0316(15) 0.0138(12) 0.043(2) 0.0229(18) O2 0.0225(11) 0.0146(10) 0.0140(9) 0.0017(7) 0.0077(9) 0.0025(8) N1 0.0330(16) 0.0121(11) 0.0192(12) 0.0006(9) 0.0145(12) 0.0029(10) N2 0.080(3) 0.0257(16) 0.059(2) -0.0026(16) 0.060(2) -0.0039(18) N3 0.051(2) 0.0252(15) 0.0104(11) 0.0028(10) 0.0107(13) 0.0141(14) C1 0.0311(17) 0.0137(13) 0.0183(13) 0.0008(10) 0.0155(13) 0.0015(12) C2 0.0209(14) 0.0133(12) 0.0115(12) 0.0020(9) 0.0060(11) 0.0054(10) C3 0.0152(13) 0.0151(12) 0.0133(12) -0.0004(10) 0.0054(11) 0.0022(10) C4 0.0222(15) 0.0181(14) 0.0192(14) -0.0009(11) 0.0101(12) 0.0060(11) C5 0.0339(19) 0.0231(16) 0.0205(15) -0.0045(12) 0.0157(14) 0.0016(14) C6 0.034(2) 0.0212(16) 0.0275(17) -0.0061(13) 0.0134(15) 0.0021(14) C7 0.037(2) 0.0167(15) 0.0318(18) -0.0057(13) 0.0188(16) -0.0056(14) C8 0.0257(17) 0.0143(14) 0.0395(19) -0.0067(12) 0.0224(16) -0.0049(12) C9 0.0190(16) 0.0220(16) 0.0348(19) -0.0065(14) 0.0072(14) -0.0031(12) C10 0.0203(18) 0.034(2) 0.058(3) -0.0150(19) 0.0055(19) 0.0010(15) C11 0.027(2) 0.040(2) 0.073(4) -0.013(2) 0.020(2) -0.0022(18) C12 0.049(3) 0.031(2) 0.113(5) -0.029(3) 0.065(3) -0.016(2) C13 0.048(2) 0.0180(16) 0.062(3) -0.0062(16) 0.043(2) -0.0074(15) C14 0.077(3) 0.0162(15) 0.0327(19) 0.0026(14) 0.039(2) 0.0043(18) C15 0.0157(13) 0.0146(12) 0.0117(12) -0.0017(9) 0.0040(10) 0.0012(10) C16 0.0242(15) 0.0163(13) 0.0098(11) -0.0019(10) 0.0056(11) 0.0021(11) C17 0.045(2) 0.0215(15) 0.0139(13) 0.0016(11) 0.0108(14) 0.0121(15) C18 0.0282(17) 0.0204(14) 0.0134(13) -0.0015(11) 0.0086(12) 0.0017(12) C19 0.0283(17) 0.0228(15) 0.0161(13) -0.0062(11) 0.0105(13) -0.0002(13) C20 0.0206(15) 0.0218(15) 0.0241(15) -0.0057(12) 0.0105(13) 0.0016(12) C21 0.0196(15) 0.0221(15) 0.0218(15) 0.0009(12) 0.0092(13) 0.0025(12) C22 0.0158(13) 0.0191(14) 0.0161(13) 0.0017(10) 0.0075(11) 0.0009(11) C23 0.0184(14) 0.0138(12) 0.0139(12) -0.0016(10) 0.0071(11) -0.0015(10) C24 0.0171(14) 0.0195(14) 0.0187(13) -0.0034(11) 0.0084(12) 0.0004(11) C25 0.0185(15) 0.0263(16) 0.0187(14) -0.0007(12) 0.0075(12) -0.0032(12) C26 0.0257(17) 0.0300(18) 0.0286(17) -0.0038(14) 0.0139(15) -0.0066(14) C27 0.0180(15) 0.0343(19) 0.0340(19) -0.0141(15) 0.0144(15) -0.0063(14) C28 0.0151(16) 0.043(2) 0.0306(18) -0.0048(16) 0.0060(14) 0.0038(14) C29 0.0164(15) 0.0322(18) 0.0297(17) 0.0027(14) 0.0071(14) 0.0039(13) O3 0.078(5) 0.044(3) 0.013(2) -0.011(2) 0.018(3) -0.038(3) C30 0.038(5) 0.051(5) 0.018(3) -0.002(3) 0.005(3) -0.029(4) O1W 0.078(2) 0.0227(13) 0.0151(11) -0.0012(9) 0.0150(14) -0.0153(14) O2W 0.199(7) 0.118(5) 0.109(4) -0.044(4) 0.121(5) -0.077(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C27 1.893(4) . ? O1 C14 1.218(6) . ? O2 C15 1.241(4) . ? N1 C1 1.467(4) . ? N1 C7 1.483(5) . ? N1 C4 1.502(4) . ? N2 C14 1.355(7) . ? N2 C13 1.397(7) . ? N2 H2B 0.8600 . ? N3 C17 1.345(4) . ? N3 C18 1.385(4) . ? N3 H2 0.7177 . ? C1 C8 1.533(5) . ? C1 C14 1.551(5) . ? C1 C2 1.561(5) . ? C2 C15 1.522(4) . ? C2 C3 1.541(4) . ? C2 H2A 0.9800 . ? C3 C24 1.512(4) . ? C3 C4 1.531(4) . ? C3 H3A 0.9800 . ? C4 C5 1.526(4) . ? C4 H4A 0.9800 . ? C5 C6 1.525(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.524(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.375(6) . ? C8 C13 1.384(5) . ? C9 C10 1.402(6) . ? C9 H9A 0.9300 . ? C10 C11 1.355(8) . ? C10 H10A 0.9300 . ? C11 C12 1.361(9) . ? C11 H11A 0.9300 . ? C12 C13 1.425(7) . ? C12 H12A 0.9300 . ? C15 C16 1.435(4) . ? C16 C17 1.388(4) . ? C16 C23 1.448(4) . ? C17 H17A 0.9300 . ? C18 C19 1.393(5) . ? C18 C23 1.420(4) . ? C19 C20 1.385(5) . ? C19 H19A 0.9300 . ? C20 C21 1.398(5) . ? C20 H20A 0.9300 . ? C21 C22 1.383(5) . ? C21 H21A 0.9300 . ? C22 C23 1.396(4) . ? C22 H22A 0.9300 . ? C24 C25 1.390(5) . ? C24 C29 1.392(5) . ? C25 C26 1.392(5) . ? C25 H25A 0.9300 . ? C26 C27 1.382(6) . ? C26 H26A 0.9300 . ? C27 C28 1.384(6) . ? C28 C29 1.395(5) . ? C28 H28A 0.9300 . ? C29 H29A 0.9300 . ? O3 C30 1.502(13) . ? C30 C33 1.575(14) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? O1W H1 0.8089 . ? 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 C7 118.1(3) . . ? C1 N1 C4 110.5(2) . . ? C7 N1 C4 108.9(2) . . ? C14 N2 C13 112.4(3) . . ? C14 N2 H2B 123.8 . . ? C13 N2 H2B 123.8 . . ? C17 N3 C18 110.0(3) . . ? C17 N3 H2 122.6 . . ? C18 N3 H2 127.4 . . ? N1 C1 C8 120.4(3) . . ? N1 C1 C14 110.8(3) . . ? C8 C1 C14 101.0(3) . . ? N1 C1 C2 101.9(3) . . ? C8 C1 C2 111.4(2) . . ? C14 C1 C2 111.7(3) . . ? C15 C2 C3 112.5(2) . . ? C15 C2 C1 114.0(3) . . ? C3 C2 C1 103.0(2) . . ? C15 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? C24 C3 C4 116.9(3) . . ? C24 C3 C2 112.6(2) . . ? C4 C3 C2 103.1(2) . . ? C24 C3 H3A 108.0 . . ? C4 C3 H3A 108.0 . . ? C2 C3 H3A 108.0 . . ? N1 C4 C5 105.4(3) . . ? N1 C4 C3 105.5(2) . . ? C5 C4 C3 117.9(3) . . ? N1 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C6 C5 C4 102.8(3) . . ? C6 C5 H5A 111.2 . . ? C4 C5 H5A 111.2 . . ? C6 C5 H5B 111.2 . . ? C4 C5 H5B 111.2 . . ? H5A C5 H5B 109.1 . . ? C7 C6 C5 103.7(3) . . ? C7 C6 H6A 111.0 . . ? C5 C6 H6A 111.0 . . ? C7 C6 H6B 111.0 . . ? C5 C6 H6B 111.0 . . ? H6A C6 H6B 109.0 . . ? N1 C7 C6 104.4(3) . . ? N1 C7 H7A 110.9 . . ? C6 C7 H7A 110.9 . . ? N1 C7 H7B 110.9 . . ? C6 C7 H7B 110.9 . . ? H7A C7 H7B 108.9 . . ? C9 C8 C13 119.1(4) . . ? C9 C8 C1 131.9(3) . . ? C13 C8 C1 108.7(4) . . ? C8 C9 C10 119.8(4) . . ? C8 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? C11 C10 C9 121.1(5) . . ? C11 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C10 C11 C12 120.6(5) . . ? C10 C11 H11A 119.7 . . ? C12 C11 H11A 119.7 . . ? C11 C12 C13 119.1(4) . . ? C11 C12 H12A 120.4 . . ? C13 C12 H12A 120.4 . . ? C8 C13 N2 109.7(4) . . ? C8 C13 C12 120.3(5) . . ? N2 C13 C12 130.0(4) . . ? O1 C14 N2 127.7(4) . . ? O1 C14 C1 124.3(4) . . ? N2 C14 C1 107.9(4) . . ? O2 C15 C16 121.5(3) . . ? O2 C15 C2 118.5(3) . . ? C16 C15 C2 120.0(3) . . ? C17 C16 C15 127.7(3) . . ? C17 C16 C23 106.4(3) . . ? C15 C16 C23 125.9(3) . . ? N3 C17 C16 110.0(3) . . ? N3 C17 H17A 125.0 . . ? C16 C17 H17A 125.0 . . ? N3 C18 C19 129.8(3) . . ? N3 C18 C23 107.4(3) . . ? C19 C18 C23 122.8(3) . . ? C20 C19 C18 116.9(3) . . ? C20 C19 H19A 121.6 . . ? C18 C19 H19A 121.6 . . ? C19 C20 C21 121.5(3) . . ? C19 C20 H20A 119.3 . . ? C21 C20 H20A 119.3 . . ? C22 C21 C20 121.3(3) . . ? C22 C21 H21A 119.3 . . ? C20 C21 H21A 119.3 . . ? C21 C22 C23 119.1(3) . . ? C21 C22 H22A 120.4 . . ? C23 C22 H22A 120.4 . . ? C22 C23 C18 118.4(3) . . ? C22 C23 C16 135.4(3) . . ? C18 C23 C16 106.2(3) . . ? C25 C24 C29 118.2(3) . . ? C25 C24 C3 120.0(3) . . ? C29 C24 C3 121.7(3) . . ? C24 C25 C26 121.9(3) . . ? C24 C25 H25A 119.1 . . ? C26 C25 H25A 119.1 . . ? C27 C26 C25 118.6(4) . . ? C27 C26 H26A 120.7 . . ? C25 C26 H26A 120.7 . . ? C26 C27 C28 121.0(3) . . ? C26 C27 Br1 119.9(3) . . ? C28 C27 Br1 119.1(3) . . ? C27 C28 C29 119.5(4) . . ? C27 C28 H28A 120.2 . . ? C29 C28 H28A 120.2 . . ? C24 C29 C28 120.7(4) . . ? C24 C29 H29A 119.6 . . ? C28 C29 H29A 119.6 . . ? O3 C30 C33 110.6(7) . . ? O3 C30 H30A 109.5 . . ? C33 C30 H30A 109.5 . . ? O3 C30 H30B 109.5 . . ? C33 C30 H30B 109.5 . . ? H30A C30 H30B 108.1 . . ? C30 C33 H33A 109.5 . . ? C30 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C30 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N1 C1 C8 -27.7(4) . . . . ? C4 N1 C1 C8 98.6(3) . . . . ? C7 N1 C1 C14 89.6(4) . . . . ? C4 N1 C1 C14 -144.1(3) . . . . ? C7 N1 C1 C2 -151.5(3) . . . . ? C4 N1 C1 C2 -25.2(3) . . . . ? N1 C1 C2 C15 160.8(2) . . . . ? C8 C1 C2 C15 31.1(3) . . . . ? C14 C1 C2 C15 -80.9(3) . . . . ? N1 C1 C2 C3 38.6(3) . . . . ? C8 C1 C2 C3 -91.1(3) . . . . ? C14 C1 C2 C3 156.8(3) . . . . ? C15 C2 C3 C24 72.3(3) . . . . ? C1 C2 C3 C24 -164.5(3) . . . . ? C15 C2 C3 C4 -160.8(3) . . . . ? C1 C2 C3 C4 -37.7(3) . . . . ? C1 N1 C4 C5 -123.5(3) . . . . ? C7 N1 C4 C5 7.9(3) . . . . ? C1 N1 C4 C3 2.0(3) . . . . ? C7 N1 C4 C3 133.3(3) . . . . ? C24 C3 C4 N1 146.6(3) . . . . ? C2 C3 C4 N1 22.6(3) . . . . ? C24 C3 C4 C5 -96.1(4) . . . . ? C2 C3 C4 C5 139.9(3) . . . . ? N1 C4 C5 C6 -28.5(3) . . . . ? C3 C4 C5 C6 -145.8(3) . . . . ? C4 C5 C6 C7 38.4(4) . . . . ? C1 N1 C7 C6 143.2(3) . . . . ? C4 N1 C7 C6 16.1(4) . . . . ? C5 C6 C7 N1 -33.8(4) . . . . ? N1 C1 C8 C9 -58.9(5) . . . . ? C14 C1 C8 C9 179.0(4) . . . . ? C2 C1 C8 C9 60.3(5) . . . . ? N1 C1 C8 C13 128.4(3) . . . . ? C14 C1 C8 C13 6.2(3) . . . . ? C2 C1 C8 C13 -112.5(3) . . . . ? C13 C8 C9 C10 1.4(5) . . . . ? C1 C8 C9 C10 -170.7(3) . . . . ? C8 C9 C10 C11 -0.7(6) . . . . ? C9 C10 C11 C12 -0.9(7) . . . . ? C10 C11 C12 C13 1.6(7) . . . . ? C9 C8 C13 N2 -179.5(3) . . . . ? C1 C8 C13 N2 -5.7(4) . . . . ? C9 C8 C13 C12 -0.7(5) . . . . ? C1 C8 C13 C12 173.2(3) . . . . ? C14 N2 C13 C8 2.6(5) . . . . ? C14 N2 C13 C12 -176.1(4) . . . . ? C11 C12 C13 C8 -0.9(6) . . . . ? C11 C12 C13 N2 177.7(4) . . . . ? C13 N2 C14 O1 -179.4(4) . . . . ? C13 N2 C14 C1 1.7(5) . . . . ? N1 C1 C14 O1 47.7(5) . . . . ? C8 C1 C14 O1 176.3(4) . . . . ? C2 C1 C14 O1 -65.2(5) . . . . ? N1 C1 C14 N2 -133.4(3) . . . . ? C8 C1 C14 N2 -4.7(4) . . . . ? C2 C1 C14 N2 113.8(4) . . . . ? C3 C2 C15 O2 16.7(4) . . . . ? C1 C2 C15 O2 -100.1(3) . . . . ? C3 C2 C15 C16 -164.9(3) . . . . ? C1 C2 C15 C16 78.3(4) . . . . ? O2 C15 C16 C17 -171.2(4) . . . . ? C2 C15 C16 C17 10.5(5) . . . . ? O2 C15 C16 C23 9.5(5) . . . . ? C2 C15 C16 C23 -168.9(3) . . . . ? C18 N3 C17 C16 0.6(5) . . . . ? C15 C16 C17 N3 -179.7(4) . . . . ? C23 C16 C17 N3 -0.2(4) . . . . ? C17 N3 C18 C19 179.4(4) . . . . ? C17 N3 C18 C23 -0.7(5) . . . . ? N3 C18 C19 C20 178.9(4) . . . . ? C23 C18 C19 C20 -0.9(5) . . . . ? C18 C19 C20 C21 1.0(5) . . . . ? C19 C20 C21 C22 -0.3(5) . . . . ? C20 C21 C22 C23 -0.6(5) . . . . ? C21 C22 C23 C18 0.7(5) . . . . ? C21 C22 C23 C16 -179.8(4) . . . . ? N3 C18 C23 C22 -179.8(3) . . . . ? C19 C18 C23 C22 0.1(5) . . . . ? N3 C18 C23 C16 0.6(4) . . . . ? C19 C18 C23 C16 -179.6(3) . . . . ? C17 C16 C23 C22 -179.8(4) . . . . ? C15 C16 C23 C22 -0.3(6) . . . . ? C17 C16 C23 C18 -0.2(4) . . . . ? C15 C16 C23 C18 179.2(3) . . . . ? C4 C3 C24 C25 128.4(3) . . . . ? C2 C3 C24 C25 -112.6(3) . . . . ? C4 C3 C24 C29 -55.1(4) . . . . ? C2 C3 C24 C29 63.9(4) . . . . ? C29 C24 C25 C26 -2.5(5) . . . . ? C3 C24 C25 C26 174.0(3) . . . . ? C24 C25 C26 C27 1.0(5) . . . . ? C25 C26 C27 C28 1.3(6) . . . . ? C25 C26 C27 Br1 -177.1(3) . . . . ? C26 C27 C28 C29 -2.0(6) . . . . ? Br1 C27 C28 C29 176.4(3) . . . . ? C25 C24 C29 C28 1.8(5) . . . . ? C3 C24 C29 C28 -174.7(3) . . . . ? C27 C28 C29 C24 0.4(6) . . . . ? _refine_diff_density_max 2.738 _refine_diff_density_min -1.144 _refine_diff_density_rms 0.145 _shelx_res_file ; a_a.res created by SHELXL-2014/7 TITL a_a P21/c CELL 0.71073 12.0254 15.9496 16.7865 90.000 115.616 90.000 ZERR 4 0.0006 0.0009 0.0007 0.000 0.003 0.000 LATT 1 SYMM - X , 0.50000 + Y , 0.50000 - Z SFAC C H Br N O UNIT 124 120 4 12 20 L.S. 10 FMAP 2 PLAN 20 ACTA BOND $H CONF WGHT 0.138400 5.419300 FVAR 0.44939 BR1 3 0.441921 -0.234128 0.263182 11.00000 0.02344 0.05171 = 0.04788 -0.01495 0.01459 -0.01497 O1 5 -0.087561 -0.565174 0.390401 11.00000 0.11253 0.02584 = 0.03161 0.01379 0.04260 0.02294 O2 5 -0.144893 -0.306203 0.191605 11.00000 0.02248 0.01458 = 0.01395 0.00166 0.00768 0.00252 N1 4 -0.102316 -0.578313 0.211411 11.00000 0.03298 0.01209 = 0.01919 0.00059 0.01447 0.00291 N2 4 -0.284948 -0.512970 0.314175 11.00000 0.07978 0.02568 = 0.05935 -0.00257 0.05970 -0.00388 AFIX 43 H2B 2 -0.311233 -0.519710 0.353944 11.00000 -1.20000 AFIX 0 N3 4 -0.111416 -0.314600 0.472705 11.00000 0.05061 0.02524 = 0.01035 0.00282 0.01069 0.01408 AFIX 3 H2 2 -0.093116 -0.326000 0.518005 11.00000 -1.20000 AFIX 0 C1 1 -0.157709 -0.509661 0.240112 11.00000 0.03107 0.01372 = 0.01834 0.00076 0.01549 0.00146 C2 1 -0.062037 -0.437725 0.257347 11.00000 0.02085 0.01325 = 0.01148 0.00195 0.00600 0.00544 AFIX 13 H2A 2 0.009497 -0.447881 0.313852 11.00000 -1.20000 AFIX 0 C3 1 -0.023153 -0.448860 0.181753 11.00000 0.01516 0.01510 = 0.01333 -0.00042 0.00537 0.00223 AFIX 13 H3A 2 -0.089522 -0.426871 0.127526 11.00000 -1.20000 AFIX 0 C4 1 -0.019984 -0.544219 0.172686 11.00000 0.02221 0.01808 = 0.01920 -0.00085 0.01015 0.00600 AFIX 13 H4A 2 0.064357 -0.564307 0.207512 11.00000 -1.20000 AFIX 0 C5 1 -0.069354 -0.580907 0.079736 11.00000 0.03387 0.02310 = 0.02054 -0.00450 0.01573 0.00161 AFIX 23 H5A 2 -0.130649 -0.544364 0.036967 11.00000 -1.20000 H5B 2 -0.003348 -0.590274 0.062206 11.00000 -1.20000 AFIX 0 C6 1 -0.126657 -0.663532 0.088818 11.00000 0.03356 0.02125 = 0.02750 -0.00612 0.01341 0.00208 AFIX 23 H6A 2 -0.188089 -0.682701 0.031941 11.00000 -1.20000 H6B 2 -0.064206 -0.706594 0.114289 11.00000 -1.20000 AFIX 0 C7 1 -0.185619 -0.642068 0.150388 11.00000 0.03681 0.01672 = 0.03181 -0.00575 0.01881 -0.00563 AFIX 23 H7A 2 -0.267858 -0.619451 0.117487 11.00000 -1.20000 H7B 2 -0.190685 -0.691283 0.182608 11.00000 -1.20000 AFIX 0 C8 1 -0.289227 -0.480057 0.181114 11.00000 0.02570 0.01434 = 0.03948 -0.00672 0.02243 -0.00495 C9 1 -0.342361 -0.448746 0.096468 11.00000 0.01902 0.02199 = 0.03483 -0.00645 0.00717 -0.00309 AFIX 43 H9A 2 -0.299328 -0.450070 0.061889 11.00000 -1.20000 AFIX 0 C10 1 -0.461558 -0.414827 0.062440 11.00000 0.02033 0.03443 = 0.05770 -0.01504 0.00545 0.00100 AFIX 43 H10A 2 -0.496679 -0.393197 0.005386 11.00000 -1.20000 AFIX 0 C11 1 -0.526440 -0.413044 0.111333 11.00000 0.02704 0.03970 = 0.07273 -0.01304 0.01986 -0.00223 AFIX 43 H11A 2 -0.604935 -0.389562 0.087818 11.00000 -1.20000 AFIX 0 C12 1 -0.477685 -0.445330 0.194557 11.00000 0.04865 0.03127 = 0.11294 -0.02874 0.06546 -0.01575 AFIX 43 H12A 2 -0.523158 -0.445332 0.227447 11.00000 -1.20000 AFIX 0 C13 1 -0.356047 -0.479133 0.230651 11.00000 0.04754 0.01800 = 0.06220 -0.00623 0.04261 -0.00740 C14 1 -0.169906 -0.533966 0.325445 11.00000 0.07725 0.01619 = 0.03270 0.00260 0.03927 0.00432 C15 1 -0.112708 -0.350546 0.258689 11.00000 0.01574 0.01462 = 0.01171 -0.00167 0.00397 0.00119 C16 1 -0.125355 -0.322229 0.335484 11.00000 0.02417 0.01632 = 0.00981 -0.00186 0.00561 0.00206 C17 1 -0.079811 -0.359897 0.418105 11.00000 0.04467 0.02148 = 0.01387 0.00159 0.01081 0.01207 AFIX 43 H17A 2 -0.034134 -0.409233 0.433434 11.00000 -1.20000 AFIX 0 C18 1 -0.180214 -0.245559 0.428496 11.00000 0.02816 0.02038 = 0.01340 -0.00149 0.00859 0.00174 C19 1 -0.232743 -0.182481 0.458554 11.00000 0.02834 0.02276 = 0.01608 -0.00625 0.01047 -0.00017 AFIX 43 H19A 2 -0.225921 -0.182510 0.515893 11.00000 -1.20000 AFIX 0 C20 1 -0.295602 -0.119725 0.399020 11.00000 0.02063 0.02183 = 0.02405 -0.00572 0.01051 0.00165 AFIX 43 H20A 2 -0.330724 -0.076093 0.417056 11.00000 -1.20000 AFIX 0 C21 1 -0.307425 -0.120512 0.312441 11.00000 0.01961 0.02212 = 0.02177 0.00091 0.00922 0.00254 AFIX 43 H21A 2 -0.350569 -0.077575 0.274012 11.00000 -1.20000 AFIX 0 C22 1 -0.256254 -0.183855 0.282797 11.00000 0.01584 0.01909 = 0.01609 0.00166 0.00747 0.00092 AFIX 43 H22A 2 -0.265432 -0.183893 0.224870 11.00000 -1.20000 AFIX 0 C23 1 -0.190619 -0.247759 0.340988 11.00000 0.01844 0.01382 = 0.01391 -0.00160 0.00711 -0.00149 C24 1 0.093674 -0.401537 0.197941 11.00000 0.01715 0.01955 = 0.01872 -0.00342 0.00838 0.00042 C25 1 0.089469 -0.333594 0.144812 11.00000 0.01852 0.02634 = 0.01874 -0.00072 0.00747 -0.00320 AFIX 43 H25A 2 0.015810 -0.321153 0.096198 11.00000 -1.20000 AFIX 0 C26 1 0.192358 -0.283684 0.162322 11.00000 0.02572 0.03005 = 0.02861 -0.00382 0.01394 -0.00656 AFIX 43 H26A 2 0.187516 -0.237943 0.126605 11.00000 -1.20000 AFIX 0 C27 1 0.301920 -0.303513 0.233918 11.00000 0.01802 0.03434 = 0.03399 -0.01406 0.01440 -0.00633 C28 1 0.310415 -0.372445 0.286322 11.00000 0.01508 0.04285 = 0.03057 -0.00480 0.00596 0.00384 AFIX 43 H28A 2 0.385247 -0.386165 0.333222 11.00000 -1.20000 AFIX 0 C29 1 0.205966 -0.421190 0.268305 11.00000 0.01636 0.03225 = 0.02974 0.00268 0.00706 0.00390 AFIX 43 H29A 2 0.211398 -0.467326 0.303684 11.00000 -1.20000 AFIX 0 O3 5 -0.366874 -0.398253 0.561444 10.50000 0.07762 0.04409 = 0.01258 -0.01081 0.01762 -0.03764 C30 1 -0.423471 -0.314063 0.527548 10.50000 0.03834 0.05113 = 0.01825 -0.00234 0.00519 -0.02938 AFIX 23 H30A 2 -0.426906 -0.304671 0.469436 10.50000 -1.20000 H30B 2 -0.372633 -0.270488 0.566669 10.50000 -1.20000 AFIX 0 C33 1 -0.557494 -0.309195 0.521910 10.50000 0.05361 AFIX 137 H33A 2 -0.610351 -0.279504 0.469360 10.50000 -1.50000 H33B 2 -0.555060 -0.280231 0.572771 10.50000 -1.50000 H33C 2 -0.588762 -0.364883 0.520163 10.50000 -1.50000 AFIX 0 O1W 5 -0.108223 -0.150772 0.139374 11.00000 0.07825 0.02269 = 0.01510 -0.00118 0.01503 -0.01527 AFIX 3 H1 2 -0.110683 -0.184082 0.174914 11.00000 -1.50000 AFIX 0 O2W 5 -0.428185 -0.507633 0.414929 11.00000 0.19938 0.11839 = 0.10942 -0.04434 0.12084 -0.07740 HKLF 4 1 -1.0000 0.0000 0.0000 0.0000 -1.0000 0.0000 1.0000 0.0000 1.0000 REM a_a P21/c REM R1 = 0.0907 for 6536 Fo > 4sig(Fo) and 0.1672 for all 11677 data REM 357 parameters refined using 0 restraints END WGHT 0.1384 5.4243 REM Highest difference peak 2.738, deepest hole -1.144, 1-sigma level 0.145 Q1 1 0.4633 -0.2582 0.3069 11.00000 0.05 2.74 Q2 1 -0.2524 -0.4659 0.5143 11.00000 0.05 1.58 Q3 1 -0.3783 -0.3459 0.4890 11.00000 0.05 1.29 Q4 1 -0.5182 -0.3449 0.5474 11.00000 0.05 1.26 Q5 1 -0.6780 -0.3600 0.5166 11.00000 0.05 1.12 Q6 1 -0.3629 -0.4326 0.5145 11.00000 0.05 1.07 Q7 1 -0.3118 -0.4025 0.5648 11.00000 0.05 0.85 Q8 1 -0.6419 -0.4103 0.5236 11.00000 0.05 0.81 Q9 1 -0.7376 -0.3856 0.4868 11.00000 0.05 0.80 Q10 1 -0.5711 -0.4037 0.5496 11.00000 0.05 0.75 Q11 1 -0.4421 -0.4541 0.2494 11.00000 0.05 0.74 Q12 1 0.0958 -0.3642 0.1737 11.00000 0.05 0.73 Q13 1 -0.4712 -0.4355 0.1011 11.00000 0.05 0.72 Q14 1 -0.0185 -0.5482 0.4129 11.00000 0.05 0.70 Q15 1 -0.0895 -0.3926 0.2508 11.00000 0.05 0.69 Q16 1 -0.0225 -0.5004 0.1797 11.00000 0.05 0.69 Q17 1 -0.2245 -0.5136 0.3608 11.00000 0.05 0.67 Q18 1 0.4441 -0.1606 0.2502 11.00000 0.05 0.63 Q19 1 -0.0274 -0.5654 0.1365 11.00000 0.05 0.61 Q20 1 -0.2251 -0.2153 0.3106 11.00000 0.05 0.60 ; _shelx_res_checksum 73555 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_a _database_code_depnum_ccdc_archive 'CCDC 1818997' _audit_update_record ; 2018-01-24 deposited with the CCDC. 2018-04-02 downloaded from the CCDC. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H13 N O' _chemical_formula_weight 247.28 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.3388(5) _cell_length_b 7.1295(3) _cell_length_c 13.1880(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.232(2) _cell_angle_gamma 90.00 _cell_volume 1244.19(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8064 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 32.88 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9725 _exptl_absorpt_correction_T_max 0.9787 _exptl_absorpt_process_details SADABS_Bruker_2014 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 20212 _diffrn_reflns_av_R_equivalents 0.0561 _diffrn_reflns_av_sigmaI/netI 0.0651 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 33.18 _reflns_number_total 4734 _reflns_number_gt 3221 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXL-2014 (Sheldrick 2014)' _computing_structure_refinement 'SHELXL-2014 (Sheldrick 2014)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0725P)^2^+0.4238P] 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 4734 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1018 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_ref 0.1517 _refine_ls_wR_factor_gt 0.1340 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 O1 O 0.41011(7) 0.46360(13) 0.30239(7) 0.0197(2) Uani 1 1 d . . . N1 N 0.38433(8) 0.16930(15) 0.60527(8) 0.0174(2) Uani 1 1 d . . . C1 C 0.29136(9) 0.23980(17) 0.56258(10) 0.0158(2) Uani 1 1 d . . . C2 C 0.19777(10) 0.22799(19) 0.59869(10) 0.0203(3) Uani 1 1 d . . . H2A H 0.1900 0.1666 0.6612 0.024 Uiso 1 1 calc R . . C3 C 0.11686(10) 0.3098(2) 0.53929(11) 0.0235(3) Uani 1 1 d . . . H3A H 0.0516 0.3026 0.5607 0.028 Uiso 1 1 calc R . . C4 C 0.12886(10) 0.4032(2) 0.44802(11) 0.0223(3) Uani 1 1 d . . . H4A H 0.0717 0.4592 0.4094 0.027 Uiso 1 1 calc R . . C5 C 0.22233(9) 0.41588(18) 0.41281(10) 0.0184(3) Uani 1 1 d . . . H5A H 0.2298 0.4804 0.3512 0.022 Uiso 1 1 calc R . . C6 C 0.30537(9) 0.33084(17) 0.47062(9) 0.0149(2) Uani 1 1 d . . . C7 C 0.41124(9) 0.31036(17) 0.45873(9) 0.0142(2) Uani 1 1 d . . . C8 C 0.45500(9) 0.21234(17) 0.54392(9) 0.0159(2) Uani 1 1 d . . . H8A H 0.5245 0.1801 0.5572 0.019 Uiso 1 1 calc R . . C9 C 0.45978(9) 0.37547(17) 0.37309(9) 0.0148(2) Uani 1 1 d . . . C10 C 0.56755(9) 0.33212(17) 0.37015(10) 0.0163(2) Uani 1 1 d . . . H10A H 0.6031 0.2594 0.4233 0.020 Uiso 1 1 calc R . . C11 C 0.61590(9) 0.39371(17) 0.29373(10) 0.0166(2) Uani 1 1 d . . . H11A H 0.5773 0.4684 0.2434 0.020 Uiso 1 1 calc R . . C12 C 0.72120(9) 0.35979(17) 0.27839(10) 0.0165(2) Uani 1 1 d . . . C13 C 0.75674(10) 0.43489(19) 0.19170(11) 0.0223(3) Uani 1 1 d . . . H13A H 0.7121 0.5049 0.1442 0.027 Uiso 1 1 calc R . . C14 C 0.85641(11) 0.4087(2) 0.17391(12) 0.0272(3) Uani 1 1 d . . . H14A H 0.8796 0.4612 0.1148 0.033 Uiso 1 1 calc R . . C15 C 0.92152(10) 0.3063(2) 0.24243(12) 0.0264(3) Uani 1 1 d . . . H15A H 0.9897 0.2883 0.2306 0.032 Uiso 1 1 calc R . . C16 C 0.88737(10) 0.2294(2) 0.32871(12) 0.0243(3) Uani 1 1 d . . . H16A H 0.9322 0.1582 0.3755 0.029 Uiso 1 1 calc R . . C17 C 0.78820(10) 0.25615(19) 0.34674(11) 0.0204(3) Uani 1 1 d . . . H17A H 0.7656 0.2036 0.4060 0.024 Uiso 1 1 calc R . . H1N1 H 0.3982(13) 0.114(3) 0.6662(14) 0.032(5) 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 O1 0.0208(4) 0.0238(5) 0.0142(4) 0.0019(4) 0.0017(3) 0.0045(4) N1 0.0204(5) 0.0176(5) 0.0139(5) 0.0020(4) 0.0014(4) 0.0015(4) C1 0.0183(6) 0.0141(5) 0.0152(6) -0.0018(4) 0.0022(4) -0.0002(4) C2 0.0229(6) 0.0184(6) 0.0207(6) -0.0012(5) 0.0075(5) -0.0027(5) C3 0.0174(6) 0.0238(7) 0.0305(8) -0.0044(6) 0.0080(5) -0.0008(5) C4 0.0162(6) 0.0241(7) 0.0261(7) -0.0025(5) 0.0007(5) 0.0032(5) C5 0.0185(6) 0.0191(6) 0.0173(6) -0.0014(5) 0.0004(5) 0.0023(5) C6 0.0160(5) 0.0145(5) 0.0142(5) -0.0029(4) 0.0019(4) 0.0003(4) C7 0.0151(5) 0.0139(5) 0.0136(6) -0.0016(4) 0.0017(4) 0.0000(4) C8 0.0167(5) 0.0154(5) 0.0156(6) -0.0023(4) 0.0018(4) 0.0011(4) C9 0.0170(5) 0.0134(5) 0.0138(6) -0.0036(4) 0.0015(4) 0.0008(4) C10 0.0171(5) 0.0158(5) 0.0160(6) -0.0005(4) 0.0022(4) 0.0013(4) C11 0.0171(5) 0.0149(5) 0.0176(6) -0.0022(4) 0.0017(5) 0.0002(4) C12 0.0173(5) 0.0144(5) 0.0185(6) -0.0020(4) 0.0052(5) -0.0027(4) C13 0.0251(6) 0.0209(6) 0.0217(7) 0.0022(5) 0.0066(5) -0.0017(5) C14 0.0277(7) 0.0290(7) 0.0275(7) -0.0009(6) 0.0136(6) -0.0076(6) C15 0.0176(6) 0.0297(7) 0.0337(8) -0.0080(6) 0.0099(6) -0.0050(5) C16 0.0176(6) 0.0252(7) 0.0301(7) -0.0022(6) 0.0031(5) -0.0003(5) C17 0.0190(6) 0.0205(6) 0.0223(7) 0.0005(5) 0.0050(5) -0.0016(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.2440(15) . ? N1 C8 1.3525(16) . ? N1 C1 1.3899(16) . ? N1 H1N1 0.895(18) . ? C1 C2 1.3936(18) . ? C1 C6 1.4086(18) . ? C2 C3 1.380(2) . ? C2 H2A 0.9500 . ? C3 C4 1.402(2) . ? C3 H3A 0.9500 . ? C4 C5 1.3871(18) . ? C4 H4A 0.9500 . ? C5 C6 1.4010(17) . ? C5 H5A 0.9500 . ? C6 C7 1.4478(16) . ? C7 C8 1.3879(17) . ? C7 C9 1.4473(17) . ? C8 H8A 0.9500 . ? C9 C10 1.4757(17) . ? C10 C11 1.3372(18) . ? C10 H10A 0.9500 . ? C11 C12 1.4641(17) . ? C11 H11A 0.9500 . ? C12 C17 1.3979(18) . ? C12 C13 1.3982(18) . ? C13 C14 1.3914(19) . ? C13 H13A 0.9500 . ? C14 C15 1.381(2) . ? C14 H14A 0.9500 . ? C15 C16 1.391(2) . ? C15 H15A 0.9500 . ? C16 C17 1.3864(19) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N1 C1 109.21(11) . . ? C8 N1 H1N1 123.9(11) . . ? C1 N1 H1N1 126.7(11) . . ? N1 C1 C2 129.18(12) . . ? N1 C1 C6 107.89(11) . . ? C2 C1 C6 122.93(12) . . ? C3 C2 C1 116.78(12) . . ? C3 C2 H2A 121.6 . . ? C1 C2 H2A 121.6 . . ? C2 C3 C4 121.48(12) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 121.51(12) . . ? C5 C4 H4A 119.2 . . ? C3 C4 H4A 119.2 . . ? C4 C5 C6 118.17(12) . . ? C4 C5 H5A 120.9 . . ? C6 C5 H5A 120.9 . . ? C5 C6 C1 119.11(11) . . ? C5 C6 C7 134.41(12) . . ? C1 C6 C7 106.48(10) . . ? C8 C7 C6 106.24(10) . . ? C8 C7 C9 127.55(11) . . ? C6 C7 C9 126.19(11) . . ? N1 C8 C7 110.17(11) . . ? N1 C8 H8A 124.9 . . ? C7 C8 H8A 124.9 . . ? O1 C9 C7 119.91(11) . . ? O1 C9 C10 120.98(11) . . ? C7 C9 C10 119.10(11) . . ? C11 C10 C9 120.99(12) . . ? C11 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C10 C11 C12 127.73(12) . . ? C10 C11 H11A 116.1 . . ? C12 C11 H11A 116.1 . . ? C17 C12 C13 118.33(12) . . ? C17 C12 C11 123.01(11) . . ? C13 C12 C11 118.66(12) . . ? C14 C13 C12 121.07(13) . . ? C14 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C15 C14 C13 119.75(13) . . ? C15 C14 H14A 120.1 . . ? C13 C14 H14A 120.1 . . ? C14 C15 C16 120.02(13) . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C17 C16 C15 120.26(14) . . ? C17 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? C16 C17 C12 120.57(13) . . ? C16 C17 H17A 119.7 . . ? C12 C17 H17A 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C1 C2 179.58(13) . . . . ? C8 N1 C1 C6 -0.08(14) . . . . ? N1 C1 C2 C3 -179.19(13) . . . . ? C6 C1 C2 C3 0.42(19) . . . . ? C1 C2 C3 C4 -1.2(2) . . . . ? C2 C3 C4 C5 0.7(2) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? C4 C5 C6 C1 -1.28(18) . . . . ? C4 C5 C6 C7 178.48(13) . . . . ? N1 C1 C6 C5 -179.50(11) . . . . ? C2 C1 C6 C5 0.82(19) . . . . ? N1 C1 C6 C7 0.68(13) . . . . ? C2 C1 C6 C7 -179.00(12) . . . . ? C5 C6 C7 C8 179.20(13) . . . . ? C1 C6 C7 C8 -1.02(13) . . . . ? C5 C6 C7 C9 -2.4(2) . . . . ? C1 C6 C7 C9 177.41(11) . . . . ? C1 N1 C8 C7 -0.60(14) . . . . ? C6 C7 C8 N1 1.01(14) . . . . ? C9 C7 C8 N1 -177.40(11) . . . . ? C8 C7 C9 O1 -179.36(12) . . . . ? C6 C7 C9 O1 2.54(19) . . . . ? C8 C7 C9 C10 1.99(19) . . . . ? C6 C7 C9 C10 -176.11(11) . . . . ? O1 C9 C10 C11 3.08(19) . . . . ? C7 C9 C10 C11 -178.29(12) . . . . ? C9 C10 C11 C12 -178.53(11) . . . . ? C10 C11 C12 C17 -1.4(2) . . . . ? C10 C11 C12 C13 178.87(13) . . . . ? C17 C12 C13 C14 -0.5(2) . . . . ? C11 C12 C13 C14 179.29(12) . . . . ? C12 C13 C14 C15 0.3(2) . . . . ? C13 C14 C15 C16 0.1(2) . . . . ? C14 C15 C16 C17 -0.5(2) . . . . ? C15 C16 C17 C12 0.3(2) . . . . ? C13 C12 C17 C16 0.15(19) . . . . ? C11 C12 C17 C16 -179.60(12) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 33.18 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.445 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.061