# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_yj292a _database_code_depnum_ccdc_archive 'CCDC 897225' #TrackingRef '13429_web_deposit_cif_file_0_Hyeung-geunPark_1345534609.CrystalStructure_9f.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C22 H24 Br N O2' _chemical_formula_moiety 'C22 H24 Br N O2' _chemical_formula_weight 414.34 _chemical_melting_point ? _chemical_absolute_configuration ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 12.297(3) _cell_length_b 5.9174(9) _cell_length_c 14.699(3) _cell_angle_alpha 90.0000 _cell_angle_beta 105.678(4) _cell_angle_gamma 90.0000 _cell_volume 1029.8(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5550 _cell_measurement_theta_min 3.35 _cell_measurement_theta_max 27.41 _cell_measurement_temperature 295 #------------------------------------------------------------------------------ _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428.00 _exptl_absorpt_coefficient_mu 2.016 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.367 _exptl_absorpt_correction_T_max 0.817 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 295 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 9888 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4281 _reflns_number_gt 2102 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1218 _refine_ls_number_restraints 238 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 4281 _refine_ls_number_parameters 239 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0521P)^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 0.002 _refine_diff_density_max 0.280 _refine_diff_density_min -0.210 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1712 Friedel Pairs' _refine_ls_abs_structure_Flack 0.009(14) 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Br Br -0.2901 2.4595 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 Br1 Br 0.77891(5) 0.99980(13) 0.30750(3) 0.1117(3) Uani 1.0 2 d . . . O1 O 0.7022(3) 0.6361(5) 0.7135(3) 0.0789(8) Uani 1.0 2 d . . . O2 O 0.7961(4) 0.8994(9) 0.8091(4) 0.1458(19) Uani 1.0 2 d . . . N1 N 0.9988(4) 0.7290(7) 0.7994(3) 0.0841(11) Uani 1.0 2 d . . . C2 C 0.8649(4) 0.5915(7) 0.5928(4) 0.0737(11) Uani 1.0 2 d . . . C3 C 1.1788(4) 0.7613(7) 0.9137(3) 0.0654(10) Uani 1.0 2 d . . . C4 C 1.2107(4) 0.9482(9) 0.8687(4) 0.0811(13) Uani 1.0 2 d . . . C5 C 0.7889(4) 0.5109(12) 0.5116(4) 0.0900(12) Uani 1.0 2 d . . . C6 C 0.8885(5) 0.9196(8) 0.5014(4) 0.0821(13) Uani 1.0 2 d . . . C7 C 0.8969(4) 0.5793(8) 0.7744(4) 0.0829(12) Uani 1.0 2 d . . . C8 C 1.0288(4) 0.4531(8) 0.9199(4) 0.0800(13) Uani 1.0 2 d . . . C9 C 0.8143(5) 0.8336(9) 0.4240(4) 0.0813(13) Uani 1.0 2 d . . . C10 C 1.2535(5) 0.6829(9) 0.9950(4) 0.0820(13) Uani 1.0 2 d . . . C11 C 0.5920(5) 0.7480(10) 0.6927(4) 0.0926(14) Uani 1.0 2 d . . . C12 C 1.0680(4) 0.6561(7) 0.8749(4) 0.0685(11) Uani 1.0 2 d . . . C13 C 1.3565(5) 0.7833(11) 1.0308(4) 0.0989(15) Uani 1.0 2 d . . . C14 C 1.3869(5) 0.9627(12) 0.9876(4) 0.1001(15) Uani 1.0 2 d . . . C15 C 0.8918(4) 0.4588(8) 0.6818(4) 0.0844(13) Uani 1.0 2 d . . . C16 C 0.9140(5) 0.8034(8) 0.5848(4) 0.0797(12) Uani 1.0 2 d . . . C17 C 0.7642(5) 0.6265(10) 0.4275(4) 0.0977(15) Uani 1.0 2 d . . . C18 C 0.7951(5) 0.7264(10) 0.7670(4) 0.0861(13) Uani 1.0 2 d . . . C19 C 1.3147(5) 1.0466(10) 0.9043(4) 0.0940(15) Uani 1.0 2 d . . . C20 C 0.9104(5) 0.4151(10) 0.8588(4) 0.1070(17) Uani 1.0 2 d . . . C21 C 0.5171(5) 0.5978(13) 0.6225(6) 0.142(3) Uani 1.0 2 d . . . C22 C 0.5524(6) 0.7790(15) 0.7749(5) 0.133(3) Uani 1.0 2 d . . . C23 C 0.6034(7) 0.9765(18) 0.6463(7) 0.173(3) Uani 1.0 2 d . . . H4 H 1.1611 1.0064 0.8144 0.0973 Uiso 1.0 2 calc R . . H5 H 0.7532 0.3734 0.5142 0.1080 Uiso 1.0 2 calc R . . H6 H 0.9225 1.0586 0.4979 0.0986 Uiso 1.0 2 calc R . . H8A H 1.0762 0.3227 0.9188 0.0960 Uiso 1.0 2 calc R . . H8B H 1.0290 0.4846 0.9847 0.0960 Uiso 1.0 2 calc R . . H10 H 1.2336 0.5595 1.0263 0.0984 Uiso 1.0 2 calc R . . H13 H 1.4059 0.7266 1.0855 0.1187 Uiso 1.0 2 calc R . . H14 H 1.4564 1.0316 1.0132 0.1202 Uiso 1.0 2 calc R . . H15A H 0.9643 0.3866 0.6885 0.1013 Uiso 1.0 2 calc R . . H15B H 0.8360 0.3394 0.6742 0.1013 Uiso 1.0 2 calc R . . H16 H 0.9648 0.8655 0.6376 0.0956 Uiso 1.0 2 calc R . . H17 H 0.7145 0.5661 0.3738 0.1172 Uiso 1.0 2 calc R . . H19 H 1.3367 1.1678 0.8731 0.1128 Uiso 1.0 2 calc R . . H20A H 0.8555 0.4486 0.8935 0.1284 Uiso 1.0 2 calc R . . H20B H 0.9004 0.2598 0.8370 0.1284 Uiso 1.0 2 calc R . . H21A H 0.5034 0.4616 0.6530 0.1699 Uiso 1.0 2 calc R . . H21B H 0.5527 0.5613 0.5737 0.1699 Uiso 1.0 2 calc R . . H21C H 0.4467 0.6733 0.5951 0.1699 Uiso 1.0 2 calc R . . H22A H 0.5943 0.8984 0.8129 0.1598 Uiso 1.0 2 calc R . . H22B H 0.5626 0.6415 0.8109 0.1598 Uiso 1.0 2 calc R . . H22C H 0.4736 0.8176 0.7560 0.1598 Uiso 1.0 2 calc R . . H23A H 0.6344 0.9529 0.5937 0.2077 Uiso 1.0 2 calc R . . H23B H 0.6525 1.0735 0.6916 0.2077 Uiso 1.0 2 calc R . . H23C H 0.5303 1.0456 0.6245 0.2077 Uiso 1.0 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.1104(5) 0.1426(5) 0.0840(4) 0.0074(5) 0.0294(3) 0.0079(4) O1 0.077(2) 0.0720(17) 0.0850(19) -0.0066(15) 0.0176(16) -0.0075(15) O2 0.111(4) 0.133(4) 0.191(5) -0.028(3) 0.036(3) -0.077(3) N1 0.078(3) 0.084(3) 0.085(3) -0.025(2) 0.013(2) 0.017(2) C2 0.069(3) 0.059(3) 0.097(3) -0.0039(19) 0.029(3) -0.009(2) C3 0.066(3) 0.066(3) 0.068(3) 0.0014(19) 0.0252(19) 0.0001(19) C4 0.073(3) 0.088(4) 0.080(3) -0.011(3) 0.018(2) -0.001(3) C5 0.089(3) 0.076(3) 0.107(3) -0.019(3) 0.029(3) -0.021(3) C6 0.087(3) 0.079(3) 0.084(3) -0.002(2) 0.030(3) -0.002(3) C7 0.078(3) 0.078(3) 0.089(3) -0.026(2) 0.016(3) 0.010(2) C8 0.089(3) 0.066(3) 0.088(3) -0.010(3) 0.029(3) 0.013(3) C9 0.081(4) 0.094(4) 0.075(3) 0.001(3) 0.031(3) -0.010(3) C10 0.077(3) 0.094(3) 0.077(3) 0.003(3) 0.025(3) 0.008(3) C11 0.088(3) 0.097(3) 0.097(3) 0.003(3) 0.032(3) -0.007(3) C12 0.074(3) 0.065(3) 0.071(3) -0.004(2) 0.028(2) 0.003(2) C13 0.081(4) 0.123(4) 0.086(3) 0.010(3) 0.010(3) 0.016(3) C14 0.075(3) 0.120(4) 0.100(3) -0.013(3) 0.015(3) -0.006(4) C15 0.076(3) 0.064(3) 0.114(3) -0.008(3) 0.028(3) 0.002(3) C16 0.079(3) 0.073(3) 0.086(3) -0.012(3) 0.021(3) -0.009(2) C17 0.091(4) 0.106(4) 0.094(3) -0.019(3) 0.020(3) -0.021(3) C18 0.083(3) 0.080(3) 0.095(3) -0.021(3) 0.023(3) -0.016(3) C19 0.089(4) 0.101(4) 0.093(3) -0.020(3) 0.027(3) 0.005(3) C20 0.105(4) 0.102(4) 0.107(4) -0.031(3) 0.019(3) 0.035(3) C21 0.090(4) 0.149(6) 0.165(6) 0.008(4) -0.002(4) -0.057(5) C22 0.106(5) 0.181(7) 0.119(5) -0.001(5) 0.041(4) -0.028(4) C23 0.159(5) 0.139(5) 0.215(6) 0.019(5) 0.039(5) 0.055(5) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Br1 C9 1.920(5) yes . . O1 C11 1.465(7) yes . . O1 C18 1.313(6) yes . . O2 C18 1.195(8) yes . . N1 C7 1.496(7) yes . . N1 C12 1.277(6) yes . . C2 C5 1.387(7) yes . . C2 C15 1.485(7) yes . . C2 C16 1.410(7) yes . . C3 C4 1.398(7) yes . . C3 C10 1.377(6) yes . . C3 C12 1.466(6) yes . . C4 C19 1.374(7) yes . . C5 C17 1.373(8) yes . . C6 C9 1.351(7) yes . . C6 C16 1.367(7) yes . . C7 C15 1.522(7) yes . . C7 C18 1.504(8) yes . . C7 C20 1.549(8) yes . . C8 C12 1.512(7) yes . . C8 C20 1.506(7) yes . . C9 C17 1.379(8) yes . . C10 C13 1.368(8) yes . . C11 C21 1.480(9) yes . . C11 C22 1.431(10) yes . . C11 C23 1.538(12) yes . . C13 C14 1.341(10) yes . . C14 C19 1.395(7) yes . . C4 H4 0.930 no . . C5 H5 0.930 no . . C6 H6 0.930 no . . C8 H8A 0.970 no . . C8 H8B 0.970 no . . C10 H10 0.930 no . . C13 H13 0.930 no . . C14 H14 0.930 no . . C15 H15A 0.970 no . . C15 H15B 0.970 no . . C16 H16 0.930 no . . C17 H17 0.930 no . . C19 H19 0.930 no . . C20 H20A 0.970 no . . C20 H20B 0.970 no . . C21 H21A 0.960 no . . C21 H21B 0.960 no . . C21 H21C 0.960 no . . C22 H22A 0.960 no . . C22 H22B 0.960 no . . C22 H22C 0.960 no . . C23 H23A 0.960 no . . C23 H23B 0.960 no . . C23 H23C 0.960 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C11 O1 C18 123.2(4) yes . . . C7 N1 C12 109.3(4) yes . . . C5 C2 C15 121.0(5) yes . . . C5 C2 C16 116.0(5) yes . . . C15 C2 C16 123.0(4) yes . . . C4 C3 C10 118.1(4) yes . . . C4 C3 C12 120.1(4) yes . . . C10 C3 C12 121.8(5) yes . . . C3 C4 C19 120.4(4) yes . . . C2 C5 C17 122.4(6) yes . . . C9 C6 C16 120.3(5) yes . . . N1 C7 C15 109.1(5) yes . . . N1 C7 C18 107.5(4) yes . . . N1 C7 C20 105.8(4) yes . . . C15 C7 C18 112.0(4) yes . . . C15 C7 C20 113.1(4) yes . . . C18 C7 C20 109.1(5) yes . . . C12 C8 C20 103.2(4) yes . . . Br1 C9 C6 119.8(4) yes . . . Br1 C9 C17 119.5(4) yes . . . C6 C9 C17 120.7(5) yes . . . C3 C10 C13 121.2(5) yes . . . O1 C11 C21 103.9(5) yes . . . O1 C11 C22 112.9(5) yes . . . O1 C11 C23 107.5(6) yes . . . C21 C11 C22 112.1(6) yes . . . C21 C11 C23 109.4(6) yes . . . C22 C11 C23 110.8(7) yes . . . N1 C12 C3 121.7(5) yes . . . N1 C12 C8 115.6(4) yes . . . C3 C12 C8 122.7(4) yes . . . C10 C13 C14 120.6(5) yes . . . C13 C14 C19 120.3(5) yes . . . C2 C15 C7 119.1(4) yes . . . C2 C16 C6 121.5(5) yes . . . C5 C17 C9 119.0(5) yes . . . O1 C18 O2 123.0(5) yes . . . O1 C18 C7 112.3(5) yes . . . O2 C18 C7 124.5(5) yes . . . C4 C19 C14 119.3(6) yes . . . C7 C20 C8 105.2(5) yes . . . C3 C4 H4 119.777 no . . . C19 C4 H4 119.783 no . . . C2 C5 H5 118.775 no . . . C17 C5 H5 118.782 no . . . C9 C6 H6 119.847 no . . . C16 C6 H6 119.841 no . . . C12 C8 H8A 111.119 no . . . C12 C8 H8B 111.113 no . . . C20 C8 H8A 111.121 no . . . C20 C8 H8B 111.115 no . . . H8A C8 H8B 109.075 no . . . C3 C10 H10 119.385 no . . . C13 C10 H10 119.390 no . . . C10 C13 H13 119.704 no . . . C14 C13 H13 119.704 no . . . C13 C14 H14 119.841 no . . . C19 C14 H14 119.842 no . . . C2 C15 H15A 107.549 no . . . C2 C15 H15B 107.547 no . . . C7 C15 H15A 107.549 no . . . C7 C15 H15B 107.542 no . . . H15A C15 H15B 107.018 no . . . C2 C16 H16 119.247 no . . . C6 C16 H16 119.246 no . . . C5 C17 H17 120.490 no . . . C9 C17 H17 120.499 no . . . C4 C19 H19 120.348 no . . . C14 C19 H19 120.350 no . . . C7 C20 H20A 110.716 no . . . C7 C20 H20B 110.707 no . . . C8 C20 H20A 110.717 no . . . C8 C20 H20B 110.718 no . . . H20A C20 H20B 108.809 no . . . C11 C21 H21A 109.477 no . . . C11 C21 H21B 109.470 no . . . C11 C21 H21C 109.471 no . . . H21A C21 H21B 109.472 no . . . H21A C21 H21C 109.473 no . . . H21B C21 H21C 109.464 no . . . C11 C22 H22A 109.467 no . . . C11 C22 H22B 109.465 no . . . C11 C22 H22C 109.464 no . . . H22A C22 H22B 109.478 no . . . H22A C22 H22C 109.479 no . . . H22B C22 H22C 109.475 no . . . C11 C23 H23A 109.472 no . . . C11 C23 H23B 109.476 no . . . C11 C23 H23C 109.472 no . . . H23A C23 H23B 109.462 no . . . H23A C23 H23C 109.471 no . . . H23B C23 H23C 109.475 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C11 O1 C18 O2 6.0(9) no . . . . C11 O1 C18 C7 -178.2(4) no . . . . C18 O1 C11 C21 173.7(5) no . . . . C18 O1 C11 C22 -64.6(6) no . . . . C18 O1 C11 C23 57.8(6) no . . . . C7 N1 C12 C3 176.4(4) no . . . . C7 N1 C12 C8 -2.6(6) no . . . . C12 N1 C7 C15 -114.3(5) no . . . . C12 N1 C7 C18 124.1(4) no . . . . C12 N1 C7 C20 7.7(6) no . . . . C5 C2 C15 C7 -135.6(5) no . . . . C15 C2 C5 C17 -178.3(5) no . . . . C5 C2 C16 C6 -0.8(8) no . . . . C16 C2 C5 C17 1.5(8) no . . . . C15 C2 C16 C6 179.1(5) no . . . . C16 C2 C15 C7 44.5(7) no . . . . C4 C3 C10 C13 -0.5(8) no . . . . C10 C3 C4 C19 1.3(7) no . . . . C4 C3 C12 N1 0.8(7) no . . . . C4 C3 C12 C8 179.7(4) no . . . . C12 C3 C4 C19 -179.5(4) no . . . . C10 C3 C12 N1 180.0(5) no . . . . C10 C3 C12 C8 -1.1(7) no . . . . C12 C3 C10 C13 -179.7(4) no . . . . C3 C4 C19 C14 -2.1(8) no . . . . C2 C5 C17 C9 -1.9(9) no . . . . C9 C6 C16 C2 0.5(9) no . . . . C16 C6 C9 Br1 179.7(5) no . . . . C16 C6 C9 C17 -0.8(8) no . . . . N1 C7 C15 C2 -70.0(5) no . . . . N1 C7 C18 O1 156.5(4) no . . . . N1 C7 C18 O2 -27.8(8) no . . . . N1 C7 C20 C8 -9.6(6) no . . . . C15 C7 C18 O1 36.8(6) no . . . . C15 C7 C18 O2 -147.5(5) no . . . . C18 C7 C15 C2 48.8(6) no . . . . C15 C7 C20 C8 109.8(5) no . . . . C20 C7 C15 C2 172.6(4) no . . . . C18 C7 C20 C8 -124.9(4) no . . . . C20 C7 C18 O1 -89.2(5) no . . . . C20 C7 C18 O2 86.5(7) no . . . . C12 C8 C20 C7 7.9(5) no . . . . C20 C8 C12 N1 -3.7(6) no . . . . C20 C8 C12 C3 177.3(5) no . . . . Br1 C9 C17 C5 -179.0(4) no . . . . C6 C9 C17 C5 1.5(9) no . . . . C3 C10 C13 C14 0.6(9) no . . . . C10 C13 C14 C19 -1.4(10) no . . . . C13 C14 C19 C4 2.2(9) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O1 N1 3.564(5) no . . O1 C2 3.023(7) no . . O1 C5 3.493(7) no . . O1 C15 2.709(7) no . . O1 C20 3.141(6) no . . O2 N1 2.727(7) no . . O2 C11 2.777(7) no . . O2 C12 3.527(7) no . . O2 C15 3.588(8) no . . O2 C20 3.188(8) no . . O2 C22 2.988(9) no . . O2 C23 2.914(9) no . . N1 C2 3.146(6) no . . N1 C4 2.842(6) no . . N1 C16 3.075(7) no . . C2 C9 2.786(7) no . . C2 C18 3.020(9) no . . C3 C14 2.765(7) no . . C4 C13 2.745(7) no . . C5 C6 2.734(8) no . . C7 C16 3.143(8) no . . C8 C10 3.010(7) no . . C8 C15 3.449(7) no . . C8 C18 3.526(7) no . . C10 C19 2.742(8) no . . C12 C15 3.285(6) no . . C12 C18 3.328(7) no . . C16 C17 2.744(7) no . . C16 C18 3.410(9) no . . C18 C21 3.585(8) no . . C18 C22 3.035(10) no . . C18 C23 2.939(10) no . . O2 C10 3.525(8) no . 2_757 O2 C20 3.357(8) no . 1_565 C10 O2 3.525(8) no . 2_747 C10 C20 3.593(9) no . 2_757 C20 O2 3.357(8) no . 1_545 C20 C10 3.593(9) no . 2_747 Br1 H6 2.8977 no . . Br1 H17 2.9293 no . . O1 H5 3.5191 no . . O1 H15B 2.5760 no . . O1 H20A 3.0141 no . . O1 H20B 3.4355 no . . O1 H21A 2.5813 no . . O1 H21B 2.4000 no . . O1 H21C 3.1613 no . . O1 H22A 2.7115 no . . O1 H22B 2.5150 no . . O1 H22C 3.2242 no . . O1 H23A 2.5534 no . . O1 H23B 2.6593 no . . O1 H23C 3.2497 no . . O2 H20A 2.9489 no . . O2 H22A 2.4975 no . . O2 H22B 3.2580 no . . O2 H23A 3.2679 no . . O2 H23B 2.3484 no . . N1 H4 2.5478 no . . N1 H8A 2.9771 no . . N1 H8B 3.0162 no . . N1 H15A 2.5635 no . . N1 H15B 3.2734 no . . N1 H16 2.4395 no . . N1 H20A 3.0133 no . . N1 H20B 3.1363 no . . C2 H6 3.2592 no . . C2 H17 3.2535 no . . C2 H23A 3.5539 no . . C3 H8A 2.8958 no . . C3 H8B 2.8643 no . . C3 H13 3.2259 no . . C3 H19 3.2464 no . . C4 H10 3.2218 no . . C4 H14 3.2276 no . . C5 H15A 2.9875 no . . C5 H15B 2.5162 no . . C5 H16 3.2166 no . . C5 H21B 3.2845 no . . C6 H17 3.2098 no . . C7 H8A 3.0242 no . . C7 H8B 3.1300 no . . C7 H16 2.9181 no . . C8 H10 2.6570 no . . C8 H15A 3.3009 no . . C9 H5 3.2061 no . . C9 H16 3.1898 no . . C10 H4 3.2210 no . . C10 H8A 3.0386 no . . C10 H8B 2.9660 no . . C10 H14 3.1922 no . . C12 H4 2.6361 no . . C12 H10 2.6413 no . . C12 H15A 3.1287 no . . C12 H16 3.5950 no . . C12 H20A 2.9656 no . . C12 H20B 3.0718 no . . C13 H19 3.2097 no . . C14 H4 3.2303 no . . C14 H10 3.1855 no . . C15 H5 2.6385 no . . C15 H16 2.7082 no . . C15 H20A 3.2602 no . . C15 H20B 2.5440 no . . C16 H5 3.2173 no . . C16 H15A 2.8771 no . . C16 H15B 3.2961 no . . C16 H23A 3.5865 no . . C17 H6 3.2100 no . . C18 H15A 3.3170 no . . C18 H15B 2.7796 no . . C18 H16 3.2859 no . . C18 H20A 2.4417 no . . C18 H20B 3.1046 no . . C18 H22A 2.9140 no . . C18 H22B 3.1370 no . . C18 H23A 3.0777 no . . C18 H23B 2.7337 no . . C19 H13 3.2137 no . . C20 H15A 2.7623 no . . C20 H15B 2.6561 no . . C21 H22A 3.2345 no . . C21 H22B 2.6859 no . . C21 H22C 2.5295 no . . C21 H23A 2.6463 no . . C21 H23B 3.2885 no . . C21 H23C 2.6543 no . . C22 H21A 2.5530 no . . C22 H21B 3.2268 no . . C22 H21C 2.6843 no . . C22 H23A 3.2592 no . . C22 H23B 2.6206 no . . C22 H23C 2.6694 no . . C23 H21A 3.2973 no . . C23 H21B 2.6839 no . . C23 H21C 2.5907 no . . C23 H22A 2.5238 no . . C23 H22B 3.2697 no . . C23 H22C 2.7241 no . . H4 H16 3.1443 no . . H4 H19 2.3057 no . . H5 H15A 3.1168 no . . H5 H15B 2.3056 no . . H5 H17 2.2925 no . . H5 H21B 3.0404 no . . H6 H16 2.2841 no . . H8A H10 2.5599 no . . H8A H15A 3.3139 no . . H8A H20A 2.7410 no . . H8A H20B 2.2030 no . . H8B H10 2.4641 no . . H8B H20A 2.2020 no . . H8B H20B 2.6695 no . . H10 H13 2.2856 no . . H13 H14 2.2649 no . . H14 H19 2.3277 no . . H15A H16 2.9313 no . . H15A H20B 2.6220 no . . H15B H16 3.5985 no . . H15B H20A 3.2313 no . . H15B H20B 2.3561 no . . H21A H22A 3.4692 no . . H21A H22B 2.4775 no . . H21A H22C 2.6769 no . . H21A H23A 3.5454 no . . H21A H23C 3.5079 no . . H21B H22B 3.4883 no . . H21B H22C 3.4404 no . . H21B H23A 2.5113 no . . H21B H23B 3.5425 no . . H21B H23C 2.9931 no . . H21C H22A 3.4889 no . . H21C H22B 3.1117 no . . H21C H22C 2.4514 no . . H21C H23A 2.8444 no . . H21C H23B 3.4764 no . . H21C H23C 2.4203 no . . H22A H23A 3.4036 no . . H22A H23B 2.3350 no . . H22A H23C 2.8046 no . . H22B H23B 3.4465 no . . H22B H23C 3.5769 no . . H22C H23A 3.5763 no . . H22C H23B 3.0252 no . . H22C H23C 2.6019 no . . Br1 H15A 3.2129 no . 2_756 Br1 H19 3.3000 no . 2_746 Br1 H21C 3.5984 no . 2_656 Br1 H22C 3.5338 no . 2_656 O1 H23B 3.3840 no . 1_545 O2 H8B 3.2464 no . 2_757 O2 H10 2.7135 no . 2_757 O2 H15B 3.3881 no . 1_565 O2 H20A 3.4847 no . 1_565 O2 H20B 2.4654 no . 1_565 N1 H20B 3.4633 no . 1_565 C2 H6 3.5953 no . 1_545 C2 H6 3.2453 no . 2_746 C3 H8A 3.5615 no . 1_565 C3 H8B 3.5455 no . 2_757 C3 H20A 3.1762 no . 2_757 C4 H8A 2.9738 no . 1_565 C5 H6 3.1756 no . 1_545 C5 H21C 3.5199 no . 2_646 C6 H5 3.1917 no . 1_565 C6 H6 3.1546 no . 2_746 C8 H8B 3.2702 no . 2_747 C8 H8B 3.5920 no . 2_757 C9 H6 3.5261 no . 2_746 C9 H15A 3.5600 no . 2_756 C10 H20A 2.8536 no . 2_757 C10 H20B 3.5227 no . 2_757 C10 H22A 3.3842 no . 2_747 C12 H8B 3.2851 no . 2_757 C13 H14 2.9557 no . 2_847 C13 H20A 3.2503 no . 2_757 C13 H22A 3.1752 no . 2_747 C13 H22B 3.1058 no . 2_757 C14 H13 3.4011 no . 2_857 C14 H14 3.1995 no . 2_847 C14 H22B 3.0473 no . 2_757 C16 H6 2.9902 no . 2_746 C17 H23C 3.5267 no . 2_646 C18 H20B 3.4611 no . 1_565 C19 H8A 3.4136 no . 1_565 C19 H13 3.5620 no . 2_857 C19 H22C 3.5647 no . 1_655 C20 H8B 3.3780 no . 2_747 C20 H10 3.4698 no . 2_747 C21 H23A 3.3323 no . 2_646 C21 H23B 3.5381 no . 1_545 C21 H23C 3.2715 no . 1_545 C21 H23C 3.5315 no . 2_646 C22 H13 3.3043 no . 2_757 C22 H14 3.4691 no . 2_747 C23 H15B 3.5116 no . 1_565 C23 H21A 3.1348 no . 1_565 C23 H21B 3.3221 no . 2_656 H4 H8A 2.7955 no . 1_565 H4 H15A 3.4527 no . 1_565 H4 H17 3.5218 no . 2_756 H5 C6 3.1917 no . 1_545 H5 H6 2.8520 no . 1_545 H5 H21C 2.8097 no . 2_646 H5 H23A 3.2576 no . 1_545 H6 C2 3.5953 no . 1_565 H6 C2 3.2453 no . 2_756 H6 C5 3.1756 no . 1_565 H6 C6 3.1546 no . 2_756 H6 C9 3.5261 no . 2_756 H6 C16 2.9902 no . 2_756 H6 H5 2.8520 no . 1_565 H6 H6 3.5111 no . 2_746 H6 H6 3.5111 no . 2_756 H6 H15A 3.3324 no . 1_565 H6 H15A 3.5407 no . 2_756 H6 H15B 3.4791 no . 1_565 H6 H16 3.2668 no . 2_756 H8A C3 3.5615 no . 1_545 H8A C4 2.9738 no . 1_545 H8A C19 3.4136 no . 1_545 H8A H4 2.7955 no . 1_545 H8A H8B 2.9461 no . 2_747 H8A H19 3.5661 no . 1_545 H8A H20A 3.4591 no . 2_747 H8B O2 3.2464 no . 2_747 H8B C3 3.5455 no . 2_747 H8B C8 3.5920 no . 2_747 H8B C8 3.2702 no . 2_757 H8B C12 3.2851 no . 2_747 H8B C20 3.3780 no . 2_757 H8B H8A 2.9461 no . 2_757 H8B H8B 3.1046 no . 2_747 H8B H8B 3.1046 no . 2_757 H8B H20A 3.3745 no . 2_757 H8B H20B 3.0068 no . 2_757 H10 O2 2.7135 no . 2_747 H10 C20 3.4698 no . 2_757 H10 H20A 2.9316 no . 2_757 H10 H20B 3.1543 no . 2_757 H10 H22A 2.8760 no . 2_747 H13 C14 3.4011 no . 2_847 H13 C19 3.5620 no . 2_847 H13 C22 3.3043 no . 2_747 H13 H14 2.7635 no . 2_847 H13 H19 3.0772 no . 2_847 H13 H20A 3.5625 no . 2_757 H13 H22A 2.4498 no . 2_747 H13 H22B 2.8597 no . 2_757 H13 H22C 3.4072 no . 2_747 H14 C13 2.9557 no . 2_857 H14 C14 3.1995 no . 2_857 H14 C22 3.4691 no . 2_757 H14 H13 2.7635 no . 2_857 H14 H14 3.2064 no . 2_847 H14 H14 3.2064 no . 2_857 H14 H19 3.4056 no . 2_847 H14 H22A 3.5348 no . 2_757 H14 H22B 2.7361 no . 2_757 H15A Br1 3.2129 no . 2_746 H15A C9 3.5600 no . 2_746 H15A H4 3.4527 no . 1_545 H15A H6 3.3324 no . 1_545 H15A H6 3.5407 no . 2_746 H15A H16 3.1736 no . 1_545 H15B O2 3.3881 no . 1_545 H15B C23 3.5116 no . 1_545 H15B H6 3.4791 no . 1_545 H15B H16 3.3355 no . 1_545 H15B H23A 3.3456 no . 1_545 H15B H23B 2.8187 no . 1_545 H16 H6 3.2668 no . 2_746 H16 H15A 3.1736 no . 1_565 H16 H15B 3.3355 no . 1_565 H17 H4 3.5218 no . 2_746 H17 H19 3.5633 no . 2_746 H17 H21A 3.4987 no . 2_656 H17 H21C 3.1676 no . 2_646 H17 H22C 2.9615 no . 2_646 H17 H23C 3.0201 no . 2_646 H19 Br1 3.3000 no . 2_756 H19 H8A 3.5661 no . 1_565 H19 H13 3.0772 no . 2_857 H19 H14 3.4056 no . 2_857 H19 H17 3.5633 no . 2_756 H19 H22C 3.4143 no . 1_655 H20A O2 3.4847 no . 1_545 H20A C3 3.1762 no . 2_747 H20A C10 2.8536 no . 2_747 H20A C13 3.2503 no . 2_747 H20A H8A 3.4591 no . 2_757 H20A H8B 3.3745 no . 2_747 H20A H10 2.9316 no . 2_747 H20A H13 3.5625 no . 2_747 H20B O2 2.4654 no . 1_545 H20B N1 3.4633 no . 1_545 H20B C10 3.5227 no . 2_747 H20B C18 3.4611 no . 1_545 H20B H8B 3.0068 no . 2_747 H20B H10 3.1543 no . 2_747 H20B H23B 3.3993 no . 1_545 H21A C23 3.1348 no . 1_545 H21A H17 3.4987 no . 2_646 H21A H23A 3.5641 no . 2_646 H21A H23B 2.8977 no . 1_545 H21A H23C 2.5333 no . 1_545 H21B C23 3.3221 no . 2_646 H21B H21C 3.3822 no . 2_646 H21B H23A 2.9495 no . 2_646 H21B H23B 3.4197 no . 1_545 H21B H23C 3.1712 no . 1_545 H21B H23C 2.8163 no . 2_646 H21C Br1 3.5984 no . 2_646 H21C C5 3.5199 no . 2_656 H21C H5 2.8097 no . 2_656 H21C H17 3.1676 no . 2_656 H21C H21B 3.3822 no . 2_656 H21C H23A 2.9839 no . 2_646 H21C H23C 3.4009 no . 2_646 H22A C10 3.3842 no . 2_757 H22A C13 3.1752 no . 2_757 H22A H10 2.8760 no . 2_757 H22A H13 2.4498 no . 2_757 H22A H14 3.5348 no . 2_747 H22B C13 3.1058 no . 2_747 H22B C14 3.0473 no . 2_747 H22B H13 2.8597 no . 2_747 H22B H14 2.7361 no . 2_747 H22C Br1 3.5338 no . 2_646 H22C C19 3.5647 no . 1_455 H22C H13 3.4072 no . 2_757 H22C H17 2.9615 no . 2_656 H22C H19 3.4143 no . 1_455 H23A C21 3.3323 no . 2_656 H23A H5 3.2576 no . 1_565 H23A H15B 3.3456 no . 1_565 H23A H21A 3.5641 no . 2_656 H23A H21B 2.9495 no . 2_656 H23A H21C 2.9839 no . 2_656 H23B O1 3.3840 no . 1_565 H23B C21 3.5381 no . 1_565 H23B H15B 2.8187 no . 1_565 H23B H20B 3.3993 no . 1_565 H23B H21A 2.8977 no . 1_565 H23B H21B 3.4197 no . 1_565 H23C C17 3.5267 no . 2_656 H23C C21 3.2715 no . 1_565 H23C C21 3.5315 no . 2_656 H23C H17 3.0201 no . 2_656 H23C H21A 2.5333 no . 1_565 H23C H21B 3.1712 no . 1_565 H23C H21B 2.8163 no . 2_656 H23C H21C 3.4009 no . 2_656 #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================