# 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_3409-5 #TrackingRef '3409-5.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C20 H17 Br N2 O4' _chemical_formula_moiety 'C20 H17 Br N2 O4' _chemical_formula_weight 429.27 _chemical_melting_point ? _chemical_absolute_configuration ad #============================================================================== # 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 9.24936(19) _cell_length_b 10.4306(2) _cell_length_c 9.62893(18) _cell_angle_alpha 90.0000 _cell_angle_beta 99.3592(13) _cell_angle_gamma 90.0000 _cell_volume 916.59(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 7904 _cell_measurement_theta_min 4.24 _cell_measurement_theta_max 68.34 _cell_measurement_temperature 123 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.030 _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436.00 _exptl_absorpt_coefficient_mu 3.314 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.577 _exptl_absorpt_correction_T_max 0.905 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 123 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 8128 _diffrn_reflns_av_R_equivalents 0.0826 _diffrn_reflns_theta_max 68.24 _diffrn_reflns_theta_full 68.24 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _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 3005 _reflns_number_gt 2703 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1429 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3005 _refine_ls_number_parameters 244 _refine_ls_goodness_of_fit_ref 0.871 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_diff_density_max 1.190 _refine_diff_density_min -0.480 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1223 Friedel Pairs' _refine_ls_abs_structure_Flack -0.01(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; 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) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Br Br -0.6763 1.2805 ; 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 1.21122(6) 0.59498(6) 0.87111(5) 0.0334(2) Uani 1.0 2 d . . . O3 O 0.4959(4) 0.0948(6) 0.4267(4) 0.0307(8) Uani 1.0 2 d . . . O4 O 0.9056(4) -0.0102(5) 0.7059(5) 0.0304(9) Uani 1.0 2 d . . . O5 O 0.7250(4) -0.0578(4) 0.8186(5) 0.0280(9) Uani 1.0 2 d . . . O27 O 0.6268(5) -0.0854(4) 0.4795(5) 0.0372(11) Uani 1.0 2 d . . . N6 N 0.8644(5) 0.3591(5) 0.4536(5) 0.0296(11) Uani 1.0 2 d . . . N7 N 0.5729(5) 0.1553(5) 0.7100(5) 0.0252(11) Uani 1.0 2 d . . . C2 C 0.6784(5) 0.1030(8) 0.6262(5) 0.0231(11) Uani 1.0 2 d . . . C8 C 1.0330(6) 0.4690(6) 0.6466(6) 0.0251(12) Uani 1.0 2 d . . . C9 C 0.9307(6) 0.3780(6) 0.5899(6) 0.0231(12) Uani 1.0 2 d . . . C10 C 0.2621(6) 0.1873(7) 0.7275(7) 0.0376(16) Uani 1.0 2 d . . . C11 C 1.0743(7) 0.4709(6) 0.7894(6) 0.0270(13) Uani 1.0 2 d . . . C12 C 0.7670(6) 0.2125(6) 0.5818(6) 0.0242(12) Uani 1.0 2 d . . . C13 C 0.5987(6) 0.0245(5) 0.5012(6) 0.0235(12) Uani 1.0 2 d . . . C14 C 0.8697(6) 0.2888(6) 0.6767(6) 0.0218(12) Uani 1.0 2 d . . . C15 C 0.7681(6) 0.2591(6) 0.4495(6) 0.0237(12) Uani 1.0 2 d . . . C16 C 0.5762(7) -0.0420(6) 0.8366(6) 0.0282(13) Uani 1.0 2 d . . . C17 C 0.3528(6) 0.0795(7) 0.7985(6) 0.0290(13) Uani 1.0 2 d . . . C18 C 1.0175(6) 0.3835(6) 0.8784(6) 0.0250(12) Uani 1.0 2 d . . . C19 C 0.5226(7) -0.1294(7) 0.9219(6) 0.0298(13) Uani 1.0 2 d . . . C20 C 0.7800(6) 0.0087(6) 0.7191(6) 0.0246(12) Uani 1.0 2 d . . . C21 C 0.5000(6) 0.0639(5) 0.7790(6) 0.0228(13) Uani 1.0 2 d . . . C22 C 0.9151(6) 0.2927(6) 0.8202(6) 0.0242(12) Uani 1.0 2 d . . . C23 C 0.4041(7) 0.0318(7) 0.3091(7) 0.0357(15) Uani 1.0 2 d . . . C24 C 0.2782(7) 0.1213(7) 0.2598(7) 0.0375(16) Uani 1.0 2 d . . . C25 C 0.2949(6) -0.0113(7) 0.8842(7) 0.0328(14) Uani 1.0 2 d . . . C26 C 0.3804(7) -0.1110(7) 0.9462(7) 0.0332(14) Uani 1.0 2 d . . . H6 H 0.8810 0.4040 0.3804 0.0355 Uiso 1.0 2 calc R . . H7 H 0.5568 0.2381 0.7163 0.0302 Uiso 1.0 2 calc R . . H8 H 1.0730 0.5281 0.5880 0.0301 Uiso 1.0 2 calc R . . H10A H 0.2440 0.1729 0.6256 0.0451 Uiso 1.0 2 calc R . . H10B H 0.3146 0.2684 0.7481 0.0451 Uiso 1.0 2 calc R . . H10C H 0.1684 0.1910 0.7624 0.0451 Uiso 1.0 2 calc R . . H15 H 0.7101 0.2266 0.3664 0.0285 Uiso 1.0 2 calc R . . H18 H 1.0489 0.3865 0.9773 0.0299 Uiso 1.0 2 calc R . . H19 H 0.5803 -0.1994 0.9624 0.0357 Uiso 1.0 2 calc R . . H22 H 0.8763 0.2334 0.8794 0.0291 Uiso 1.0 2 calc R . . H23A H 0.3673 -0.0510 0.3396 0.0428 Uiso 1.0 2 calc R . . H23B H 0.4608 0.0152 0.2322 0.0428 Uiso 1.0 2 calc R . . H24A H 0.2215 0.0886 0.1721 0.0450 Uiso 1.0 2 calc R . . H24B H 0.3164 0.2067 0.2433 0.0450 Uiso 1.0 2 calc R . . H24C H 0.2149 0.1269 0.3319 0.0450 Uiso 1.0 2 calc R . . H25 H 0.1963 -0.0036 0.8991 0.0393 Uiso 1.0 2 calc R . . H26 H 0.3408 -0.1682 1.0070 0.0398 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 0.0393(4) 0.0328(4) 0.0279(3) -0.0131(3) 0.0049(2) -0.0024(3) O3 0.0312(19) 0.0223(19) 0.0355(19) -0.001(2) -0.0044(15) -0.004(3) O4 0.025(3) 0.028(3) 0.039(3) 0.0007(18) 0.0052(17) 0.001(2) O5 0.026(2) 0.026(3) 0.034(3) 0.0008(16) 0.0095(16) 0.0017(19) O27 0.044(3) 0.023(3) 0.042(3) 0.0055(19) -0.001(2) -0.0067(19) N6 0.038(3) 0.026(3) 0.025(3) -0.005(3) 0.009(2) 0.001(2) N7 0.028(3) 0.016(3) 0.034(3) -0.0008(18) 0.012(2) -0.002(2) C2 0.025(3) 0.019(3) 0.027(3) 0.001(3) 0.0100(19) -0.006(3) C8 0.032(3) 0.019(3) 0.025(3) -0.000(3) 0.009(3) 0.004(3) C9 0.020(3) 0.025(3) 0.025(3) 0.001(3) 0.007(2) -0.000(3) C10 0.018(3) 0.050(5) 0.047(4) -0.000(3) 0.013(3) -0.009(4) C11 0.032(3) 0.021(3) 0.028(3) -0.001(3) 0.007(3) -0.003(3) C12 0.026(3) 0.019(3) 0.027(3) -0.001(3) 0.004(3) -0.003(3) C13 0.027(3) 0.018(4) 0.027(3) -0.005(3) 0.009(3) -0.002(3) C14 0.015(3) 0.027(3) 0.026(3) -0.002(2) 0.010(2) -0.002(3) C15 0.024(3) 0.024(3) 0.024(3) -0.002(3) 0.004(3) -0.005(3) C16 0.032(3) 0.027(4) 0.026(3) -0.007(3) 0.007(3) -0.005(3) C17 0.030(3) 0.030(4) 0.028(3) -0.006(3) 0.008(2) -0.005(3) C18 0.019(3) 0.027(3) 0.030(3) 0.002(3) 0.006(2) 0.004(3) C19 0.034(4) 0.032(4) 0.025(3) -0.007(3) 0.008(3) 0.001(3) C20 0.029(3) 0.022(3) 0.023(3) -0.004(3) 0.002(3) -0.000(3) C21 0.017(3) 0.027(4) 0.027(3) -0.006(2) 0.011(2) -0.002(3) C22 0.024(3) 0.023(3) 0.029(3) 0.003(3) 0.015(3) 0.006(3) C23 0.029(4) 0.033(4) 0.044(4) -0.007(3) 0.003(3) -0.007(3) C24 0.031(3) 0.036(5) 0.043(4) -0.003(3) -0.001(3) 0.003(3) C25 0.021(3) 0.040(4) 0.040(4) -0.011(3) 0.012(3) -0.010(3) C26 0.047(4) 0.026(4) 0.028(3) -0.017(3) 0.009(3) -0.005(3) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR2002 (Burla, et al., 2003)' _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 C11 1.890(6) yes . . O3 C13 1.317(7) yes . . O3 C23 1.456(8) yes . . O4 C20 1.205(7) yes . . O5 C16 1.424(8) yes . . O5 C20 1.348(8) yes . . O27 C13 1.200(7) yes . . N6 C9 1.370(7) yes . . N6 C15 1.369(8) yes . . N7 C2 1.468(8) yes . . N7 C21 1.397(8) yes . . C2 C12 1.507(9) yes . . C2 C13 1.542(8) yes . . C2 C20 1.542(8) yes . . C8 C9 1.388(8) yes . . C8 C11 1.366(8) yes . . C9 C14 1.427(9) yes . . C10 C17 1.499(9) yes . . C11 C18 1.411(9) yes . . C12 C14 1.445(8) yes . . C12 C15 1.364(8) yes . . C14 C22 1.378(8) yes . . C16 C19 1.372(9) yes . . C16 C21 1.377(8) yes . . C17 C21 1.414(8) yes . . C17 C25 1.417(9) yes . . C18 C22 1.391(8) yes . . C19 C26 1.387(9) yes . . C23 C24 1.508(9) yes . . C25 C26 1.381(9) yes . . N6 H6 0.880 no . . N7 H7 0.880 no . . C8 H8 0.950 no . . C10 H10A 0.980 no . . C10 H10B 0.980 no . . C10 H10C 0.980 no . . C15 H15 0.950 no . . C18 H18 0.950 no . . C19 H19 0.950 no . . C22 H22 0.950 no . . C23 H23A 0.990 no . . C23 H23B 0.990 no . . C24 H24A 0.980 no . . C24 H24B 0.980 no . . C24 H24C 0.980 no . . C25 H25 0.950 no . . C26 H26 0.950 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 C13 O3 C23 116.7(5) yes . . . C16 O5 C20 120.7(5) yes . . . C9 N6 C15 109.0(5) yes . . . C2 N7 C21 115.0(5) yes . . . N7 C2 C12 108.4(6) yes . . . N7 C2 C13 110.5(4) yes . . . N7 C2 C20 108.4(5) yes . . . C12 C2 C13 113.2(5) yes . . . C12 C2 C20 109.9(4) yes . . . C13 C2 C20 106.4(6) yes . . . C9 C8 C11 117.8(6) yes . . . N6 C9 C8 130.2(6) yes . . . N6 C9 C14 108.0(5) yes . . . C8 C9 C14 121.7(5) yes . . . Br1 C11 C8 119.2(5) yes . . . Br1 C11 C18 118.7(4) yes . . . C8 C11 C18 122.1(6) yes . . . C2 C12 C14 124.7(5) yes . . . C2 C12 C15 128.4(5) yes . . . C14 C12 C15 106.9(5) yes . . . O3 C13 O27 126.5(5) yes . . . O3 C13 C2 109.9(5) yes . . . O27 C13 C2 123.6(5) yes . . . C9 C14 C12 105.7(5) yes . . . C9 C14 C22 118.9(5) yes . . . C12 C14 C22 135.4(6) yes . . . N6 C15 C12 110.4(5) yes . . . O5 C16 C19 116.5(5) yes . . . O5 C16 C21 119.0(6) yes . . . C19 C16 C21 124.2(6) yes . . . C10 C17 C21 120.4(6) yes . . . C10 C17 C25 122.0(5) yes . . . C21 C17 C25 117.6(6) yes . . . C11 C18 C22 119.5(5) yes . . . C16 C19 C26 117.0(6) yes . . . O4 C20 O5 118.2(5) yes . . . O4 C20 C2 123.4(6) yes . . . O5 C20 C2 118.4(5) yes . . . N7 C21 C16 119.0(5) yes . . . N7 C21 C17 122.3(5) yes . . . C16 C21 C17 118.7(6) yes . . . C14 C22 C18 120.0(6) yes . . . O3 C23 C24 106.8(6) yes . . . C17 C25 C26 120.8(6) yes . . . C19 C26 C25 121.5(6) yes . . . C9 N6 H6 125.527 no . . . C15 N6 H6 125.522 no . . . C2 N7 H7 122.491 no . . . C21 N7 H7 122.498 no . . . C9 C8 H8 121.081 no . . . C11 C8 H8 121.078 no . . . C17 C10 H10A 109.473 no . . . C17 C10 H10B 109.477 no . . . C17 C10 H10C 109.464 no . . . H10A C10 H10B 109.473 no . . . H10A C10 H10C 109.472 no . . . H10B C10 H10C 109.468 no . . . N6 C15 H15 124.802 no . . . C12 C15 H15 124.795 no . . . C11 C18 H18 120.240 no . . . C22 C18 H18 120.243 no . . . C16 C19 H19 121.482 no . . . C26 C19 H19 121.481 no . . . C14 C22 H22 119.999 no . . . C18 C22 H22 119.997 no . . . O3 C23 H23A 110.367 no . . . O3 C23 H23B 110.369 no . . . C24 C23 H23A 110.366 no . . . C24 C23 H23B 110.374 no . . . H23A C23 H23B 108.598 no . . . C23 C24 H24A 109.474 no . . . C23 C24 H24B 109.471 no . . . C23 C24 H24C 109.475 no . . . H24A C24 H24B 109.464 no . . . H24A C24 H24C 109.472 no . . . H24B C24 H24C 109.472 no . . . C17 C25 H25 119.627 no . . . C26 C25 H25 119.617 no . . . C19 C26 H26 119.243 no . . . C25 C26 H26 119.246 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 C13 O3 C23 C24 168.8(5) no . . . . C23 O3 C13 O27 2.1(9) no . . . . C23 O3 C13 C2 -176.4(4) no . . . . C16 O5 C20 O4 -178.3(5) no . . . . C16 O5 C20 C2 0.6(7) no . . . . C20 O5 C16 C19 168.5(5) no . . . . C20 O5 C16 C21 -17.0(7) no . . . . C9 N6 C15 C12 1.2(7) no . . . . C15 N6 C9 C8 -178.4(5) no . . . . C15 N6 C9 C14 -2.1(6) no . . . . C2 N7 C21 C16 38.2(6) no . . . . C2 N7 C21 C17 -145.3(4) no . . . . C21 N7 C2 C12 -169.5(4) no . . . . C21 N7 C2 C13 65.9(6) no . . . . C21 N7 C2 C20 -50.3(6) no . . . . N7 C2 C12 C14 67.1(6) no . . . . N7 C2 C12 C15 -113.0(6) no . . . . N7 C2 C13 O3 54.4(7) no . . . . N7 C2 C13 O27 -124.1(6) no . . . . N7 C2 C20 O4 -149.6(5) no . . . . N7 C2 C20 O5 31.6(7) no . . . . C12 C2 C13 O3 -67.3(6) no . . . . C12 C2 C13 O27 114.1(6) no . . . . C13 C2 C12 C14 -169.9(5) no . . . . C13 C2 C12 C15 9.9(8) no . . . . C12 C2 C20 O4 -31.3(8) no . . . . C12 C2 C20 O5 149.8(5) no . . . . C20 C2 C12 C14 -51.2(7) no . . . . C20 C2 C12 C15 128.7(6) no . . . . C13 C2 C20 O4 91.6(6) no . . . . C13 C2 C20 O5 -87.3(6) no . . . . C20 C2 C13 O3 171.9(5) no . . . . C20 C2 C13 O27 -6.7(7) no . . . . C9 C8 C11 Br1 -179.1(5) no . . . . C9 C8 C11 C18 0.6(9) no . . . . C11 C8 C9 N6 175.9(6) no . . . . C11 C8 C9 C14 0.1(9) no . . . . N6 C9 C14 C12 2.2(6) no . . . . N6 C9 C14 C22 -177.3(5) no . . . . C8 C9 C14 C12 178.8(5) no . . . . C8 C9 C14 C22 -0.7(8) no . . . . Br1 C11 C18 C22 179.1(4) no . . . . C8 C11 C18 C22 -0.6(9) no . . . . C2 C12 C14 C9 178.4(5) no . . . . C2 C12 C14 C22 -2.2(10) no . . . . C2 C12 C15 N6 -179.7(5) no . . . . C14 C12 C15 N6 0.2(7) no . . . . C15 C12 C14 C9 -1.4(6) no . . . . C15 C12 C14 C22 178.0(6) no . . . . C9 C14 C22 C18 0.7(8) no . . . . C12 C14 C22 C18 -178.7(6) no . . . . O5 C16 C19 C26 176.6(5) no . . . . O5 C16 C21 N7 -2.8(8) no . . . . O5 C16 C21 C17 -179.4(4) no . . . . C19 C16 C21 N7 171.3(5) no . . . . C19 C16 C21 C17 -5.4(8) no . . . . C21 C16 C19 C26 2.5(9) no . . . . C10 C17 C21 N7 8.7(8) no . . . . C10 C17 C21 C16 -174.8(5) no . . . . C10 C17 C25 C26 178.8(5) no . . . . C21 C17 C25 C26 0.2(8) no . . . . C25 C17 C21 N7 -172.7(5) no . . . . C25 C17 C21 C16 3.8(8) no . . . . C11 C18 C22 C14 -0.1(8) no . . . . C16 C19 C26 C25 1.9(9) no . . . . C17 C25 C26 C19 -3.1(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 O3 N7 2.778(6) no . . O3 C12 2.967(7) no . . O3 C15 3.023(7) no . . O3 C21 3.402(7) no . . O4 O27 3.192(6) no . . O4 N7 3.534(7) no . . O4 C12 2.824(7) no . . O4 C13 3.202(7) no . . O4 C14 3.144(8) no . . O4 C16 3.496(8) no . . O4 C22 3.342(8) no . . O5 O27 3.256(6) no . . O5 N7 2.745(6) no . . O5 C13 3.207(7) no . . O27 N7 3.440(7) no . . O27 C12 3.448(7) no . . O27 C16 3.573(8) no . . O27 C20 2.688(7) no . . O27 C23 2.707(8) no . . N6 C22 3.553(8) no . . N7 C10 2.926(8) no . . N7 C14 3.141(7) no . . N7 C15 3.492(8) no . . N7 C22 3.479(7) no . . C2 C16 2.812(9) no . . C2 C22 3.296(8) no . . C8 C15 3.590(8) no . . C8 C22 2.822(9) no . . C9 C18 2.763(8) no . . C11 C14 2.775(8) no . . C13 C15 2.991(8) no . . C13 C16 3.343(8) no . . C13 C21 2.992(8) no . . C14 C20 3.083(9) no . . C16 C25 2.733(9) no . . C17 C19 2.832(9) no . . C20 C21 2.803(8) no . . C20 C22 3.300(9) no . . C21 C26 2.779(9) no . . Br1 O5 3.352(4) no . 2_757 Br1 C15 3.562(6) no . 2_756 Br1 C16 3.468(6) no . 2_757 Br1 C26 3.465(7) no . 1_665 O4 N6 3.131(7) no . 2_746 O4 C8 3.538(7) no . 2_746 O5 Br1 3.352(4) no . 2_747 O5 C18 3.507(7) no . 2_747 O5 C24 3.431(8) no . 2_646 O27 C8 3.598(8) no . 2_746 O27 C10 3.365(9) no . 2_646 N6 O4 3.131(7) no . 2_756 C8 O4 3.538(7) no . 2_756 C8 O27 3.598(8) no . 2_756 C8 C24 3.530(9) no . 2_656 C10 O27 3.365(9) no . 2_656 C10 C11 3.530(10) no . 1_455 C10 C18 3.534(9) no . 1_455 C11 C10 3.530(10) no . 1_655 C11 C24 3.580(9) no . 2_656 C15 Br1 3.562(6) no . 2_746 C16 Br1 3.468(6) no . 2_747 C18 O5 3.507(7) no . 2_757 C18 C10 3.534(9) no . 1_655 C24 O5 3.431(8) no . 2_656 C24 C8 3.530(9) no . 2_646 C24 C11 3.580(9) no . 2_646 C26 Br1 3.465(7) no . 1_445 Br1 H8 2.9015 no . . Br1 H18 2.9202 no . . O3 H7 3.1331 no . . O3 H10A 3.3485 no . . O3 H15 2.5551 no . . O3 H24A 3.2298 no . . O3 H24B 2.5068 no . . O3 H24C 2.6326 no . . O4 H22 3.0775 no . . O5 H7 3.5239 no . . O5 H19 2.5478 no . . O5 H22 3.3555 no . . O27 H15 3.5562 no . . O27 H23A 2.5793 no . . O27 H23B 2.8182 no . . N6 H8 2.7734 no . . N7 H10A 3.0243 no . . N7 H10B 2.7423 no . . N7 H22 3.1166 no . . C2 H15 2.8716 no . . C2 H22 3.1135 no . . C8 H6 2.7987 no . . C8 H18 3.2786 no . . C9 H15 3.1400 no . . C9 H22 3.2797 no . . C10 H7 2.7963 no . . C10 H25 2.7191 no . . C11 H22 3.2804 no . . C12 H6 3.0867 no . . C12 H7 2.5192 no . . C12 H22 2.8887 no . . C13 H7 3.1093 no . . C13 H15 2.7621 no . . C13 H23A 2.5567 no . . C13 H23B 2.6966 no . . C14 H6 3.1129 no . . C14 H7 3.0268 no . . C14 H8 3.3190 no . . C14 H15 3.1765 no . . C14 H18 3.2563 no . . C15 H7 3.4778 no . . C16 H7 3.1376 no . . C16 H26 3.2141 no . . C17 H7 2.7223 no . . C17 H26 3.2851 no . . C18 H8 3.2900 no . . C19 H25 3.2654 no . . C20 H7 3.1578 no . . C20 H22 2.8680 no . . C21 H10A 2.8189 no . . C21 H10B 2.7236 no . . C21 H10C 3.3216 no . . C21 H19 3.2836 no . . C21 H25 3.2839 no . . C22 H7 3.3508 no . . C23 H15 3.4551 no . . C25 H10A 3.1197 no . . C25 H10B 3.2163 no . . C25 H10C 2.5982 no . . C25 H19 3.2764 no . . H6 H8 2.7690 no . . H6 H15 2.4231 no . . H7 H10A 2.9625 no . . H7 H10B 2.3316 no . . H7 H22 3.1139 no . . H10A H24C 2.8377 no . . H10A H25 3.3013 no . . H10B H25 3.4473 no . . H10C H25 2.4100 no . . H15 H23B 3.2992 no . . H18 H22 2.3444 no . . H19 H26 2.3470 no . . H23A H24A 2.4149 no . . H23A H24B 2.8568 no . . H23A H24C 2.3238 no . . H23B H24A 2.3241 no . . H23B H24B 2.4146 no . . H23B H24C 2.8568 no . . H25 H26 2.3154 no . . Br1 H15 2.8613 no . 2_756 Br1 H22 3.0236 no . 2_757 Br1 H23B 3.4449 no . 2_756 Br1 H26 2.9562 no . 1_665 O4 H6 2.4328 no . 2_746 O4 H8 2.8967 no . 2_746 O4 H10C 3.1906 no . 1_655 O4 H18 3.1977 no . 2_747 O4 H25 3.0113 no . 1_655 O5 H18 2.6901 no . 2_747 O5 H24B 2.5427 no . 2_646 O27 H7 2.9644 no . 2_646 O27 H8 3.1819 no . 2_746 O27 H10A 3.0342 no . 2_646 O27 H10B 2.7945 no . 2_646 O27 H24B 3.4129 no . 2_646 N6 H8 3.5343 no . 2_746 N6 H10A 3.4708 no . 2_656 N6 H23A 3.2903 no . 2_656 N7 H23A 3.1633 no . 2_656 N7 H26 3.2777 no . 2_657 C2 H8 3.4203 no . 2_746 C8 H10B 3.3597 no . 1_655 C8 H10C 3.2818 no . 1_655 C8 H24A 3.3883 no . 2_656 C8 H24C 2.8574 no . 2_656 C9 H10A 3.5729 no . 1_655 C9 H10C 3.1951 no . 1_655 C9 H23A 3.0360 no . 2_656 C9 H24C 3.0742 no . 2_656 C10 H6 3.3336 no . 2_646 C10 H19 3.3202 no . 2_657 C11 H10B 3.1377 no . 1_655 C11 H10C 3.0700 no . 1_655 C11 H24A 3.0759 no . 2_656 C11 H24C 3.1859 no . 2_656 C12 H8 3.0579 no . 2_746 C12 H23A 2.9167 no . 2_656 C13 H8 3.2877 no . 2_746 C14 H10C 2.9346 no . 1_655 C14 H23A 2.7411 no . 2_656 C15 H8 2.8756 no . 2_746 C15 H23A 3.2313 no . 2_656 C16 H24B 2.9495 no . 2_646 C17 H6 3.1277 no . 2_646 C17 H19 3.2466 no . 2_657 C18 H10B 3.4187 no . 1_655 C18 H10C 2.7807 no . 1_655 C18 H24A 3.0577 no . 2_656 C18 H25 3.3561 no . 2_657 C19 H10B 3.4566 no . 2_647 C19 H15 3.5566 no . 2_646 C19 H23B 3.4763 no . 1_556 C19 H24B 2.9058 no . 2_646 C20 H6 3.5939 no . 2_746 C20 H8 3.4557 no . 2_746 C20 H18 3.3424 no . 2_747 C20 H24B 3.3096 no . 2_646 C22 H10C 2.7110 no . 1_655 C22 H23A 3.2469 no . 2_656 C22 H24A 3.3401 no . 2_656 C22 H26 3.1326 no . 2_657 C23 H7 3.0990 no . 2_646 C23 H26 3.5504 no . 1_554 C24 H19 3.2709 no . 2_656 C25 H6 2.9277 no . 2_646 C25 H23B 3.4621 no . 1_556 C25 H24A 3.1377 no . 1_556 C26 H7 3.5723 no . 2_647 C26 H15 3.4369 no . 2_646 C26 H22 3.5194 no . 2_647 C26 H23B 3.0331 no . 1_556 C26 H24A 3.5014 no . 1_556 H6 O4 2.4328 no . 2_756 H6 C10 3.3336 no . 2_656 H6 C17 3.1277 no . 2_656 H6 C20 3.5939 no . 2_756 H6 C25 2.9277 no . 2_656 H6 H10A 3.0300 no . 2_656 H6 H10C 3.2947 no . 2_656 H6 H25 2.8386 no . 2_656 H7 O27 2.9644 no . 2_656 H7 C23 3.0990 no . 2_656 H7 C26 3.5723 no . 2_657 H7 H19 3.5893 no . 2_657 H7 H23A 2.3971 no . 2_656 H7 H23B 2.9415 no . 2_656 H7 H26 2.8515 no . 2_657 H8 O4 2.8967 no . 2_756 H8 O27 3.1819 no . 2_756 H8 N6 3.5343 no . 2_756 H8 C2 3.4203 no . 2_756 H8 C12 3.0579 no . 2_756 H8 C13 3.2877 no . 2_756 H8 C15 2.8756 no . 2_756 H8 C20 3.4557 no . 2_756 H8 H15 2.8670 no . 2_756 H8 H24C 3.0679 no . 2_656 H10A O27 3.0342 no . 2_656 H10A N6 3.4708 no . 2_646 H10A C9 3.5729 no . 1_455 H10A H6 3.0300 no . 2_646 H10B O27 2.7945 no . 2_656 H10B C8 3.3597 no . 1_455 H10B C11 3.1377 no . 1_455 H10B C18 3.4187 no . 1_455 H10B C19 3.4566 no . 2_657 H10B H19 2.8194 no . 2_657 H10B H23B 3.2939 no . 2_656 H10C O4 3.1906 no . 1_455 H10C C8 3.2818 no . 1_455 H10C C9 3.1951 no . 1_455 H10C C11 3.0700 no . 1_455 H10C C14 2.9346 no . 1_455 H10C C18 2.7807 no . 1_455 H10C C22 2.7110 no . 1_455 H10C H6 3.2947 no . 2_646 H10C H18 3.2258 no . 1_455 H10C H19 3.4244 no . 2_657 H10C H22 3.1227 no . 1_455 H15 Br1 2.8613 no . 2_746 H15 C19 3.5566 no . 2_656 H15 C26 3.4369 no . 2_656 H15 H8 2.8670 no . 2_746 H18 O4 3.1977 no . 2_757 H18 O5 2.6901 no . 2_757 H18 C20 3.3424 no . 2_757 H18 H10C 3.2258 no . 1_655 H18 H19 3.5008 no . 2_757 H18 H24A 3.4051 no . 2_656 H18 H25 2.9577 no . 2_657 H19 C10 3.3202 no . 2_647 H19 C17 3.2466 no . 2_647 H19 C24 3.2709 no . 2_646 H19 H7 3.5893 no . 2_647 H19 H10B 2.8194 no . 2_647 H19 H10C 3.4244 no . 2_647 H19 H18 3.5008 no . 2_747 H19 H23B 3.5053 no . 2_646 H19 H24A 3.2713 no . 2_646 H19 H24B 2.5323 no . 2_646 H22 Br1 3.0236 no . 2_747 H22 C26 3.5194 no . 2_657 H22 H10C 3.1227 no . 1_655 H22 H26 2.6449 no . 2_657 H23A N6 3.2903 no . 2_646 H23A N7 3.1633 no . 2_646 H23A C9 3.0360 no . 2_646 H23A C12 2.9167 no . 2_646 H23A C14 2.7411 no . 2_646 H23A C15 3.2313 no . 2_646 H23A C22 3.2469 no . 2_646 H23A H7 2.3971 no . 2_646 H23A H26 3.3998 no . 1_554 H23B Br1 3.4449 no . 2_746 H23B C19 3.4763 no . 1_554 H23B C25 3.4621 no . 1_554 H23B C26 3.0331 no . 1_554 H23B H7 2.9415 no . 2_646 H23B H10B 3.2939 no . 2_646 H23B H19 3.5053 no . 2_656 H23B H26 2.9682 no . 1_554 H24A C8 3.3883 no . 2_646 H24A C11 3.0759 no . 2_646 H24A C18 3.0577 no . 2_646 H24A C22 3.3401 no . 2_646 H24A C25 3.1377 no . 1_554 H24A C26 3.5014 no . 1_554 H24A H18 3.4051 no . 2_646 H24A H19 3.2713 no . 2_656 H24A H25 2.7729 no . 1_554 H24A H26 3.3893 no . 1_554 H24B O5 2.5427 no . 2_656 H24B O27 3.4129 no . 2_656 H24B C16 2.9495 no . 2_656 H24B C19 2.9058 no . 2_656 H24B C20 3.3096 no . 2_656 H24B H19 2.5323 no . 2_656 H24C C8 2.8574 no . 2_646 H24C C9 3.0742 no . 2_646 H24C C11 3.1859 no . 2_646 H24C H8 3.0679 no . 2_646 H25 O4 3.0113 no . 1_455 H25 C18 3.3561 no . 2_647 H25 H6 2.8386 no . 2_646 H25 H18 2.9577 no . 2_647 H25 H24A 2.7729 no . 1_556 H26 Br1 2.9562 no . 1_445 H26 N7 3.2777 no . 2_647 H26 C22 3.1326 no . 2_647 H26 C23 3.5504 no . 1_556 H26 H7 2.8515 no . 2_647 H26 H22 2.6449 no . 2_647 H26 H23A 3.3998 no . 1_556 H26 H23B 2.9682 no . 1_556 H26 H24A 3.3893 no . 1_556 #============================================================================== #============================================================================== # 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 #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 933242'