# Electronic Supplementary Material (ESI) for Chemical Communications # 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_2483 _audit_creation_method 'SHELXL-2012 & ZCIF' _chemical_name_systematic ; Organics ; _chemical_name_common XXU-33-BrCl _chemical_formula_moiety 'C27 H25 Br Cl N O4' _chemical_formula_sum 'C27 H25 Br Cl N O4' _chemical_formula_weight 542.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _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+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.7782(6) _cell_length_b 10.1868(6) _cell_length_c 25.4096(14) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2531.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 17359 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 30.2 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.425 _exptl_crystal_F_000 1112 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.40 _exptl_absorpt_coefficient_mu 1.763 _shelx_estimated_absorpt_T_min 0.479 _shelx_estimated_absorpt_T_max 0.539 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.440 _exptl_absorpt_correction_T_max 0.494 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'sealed tube' _diffrn_measurement_device_type 'Bruker Smart Apex II diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 42520 _diffrn_reflns_av_unetI/netI 0.0188 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.154 _diffrn_reflns_theta_max 29.993 _diffrn_reflns_theta_full 25.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 7377 _reflns_number_gt 6754 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.781 _reflns_Friedel_fraction_max 1.000 _reflns_Friedel_fraction_full 1.000 _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. These statistics refer to single and composite reflections containing twin component 1 only. ; _computing_data_collection 'Apex2 (Bruker, 2010)' _computing_cell_refinement Apex2 _computing_data_reduction 'Apex2, Saint' _computing_structure_solution 'ShelXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'ShelXL-2012 (Sheldrick, 2012)' _computing_molecular_graphics 'XSHEL (Bruker, 2004)' _computing_publication_material 'Apex2, SHELXL-2012' _refine_special_details ; H atoms were p0sitioned from geometric consideration and refined as riding on the attached atoms with Uiso refined. Exeption H atom from OH which was freely refined. ; _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^)+(0.0110P)^2^+1.0680P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment refU _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0014(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; Refined as an inversion twin yielding the 2nd component near 0 within s.u. Thus the measured crystal was enantiopure. ; _refine_ls_abs_structure_Flack -0.001(5) _chemical_absolute_configuration ad _refine_ls_number_reflns 7377 # 4143 w/o Fiedel pairs _refine_ls_number_parameters 340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0302 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0498 _refine_ls_wR_factor_gt 0.0485 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_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 N1 N 0.60058(17) 0.37781(15) 0.67695(6) 0.0205(3) Uani 1 1 d . . . . . C2 C 0.7056(2) 0.47263(17) 0.65879(7) 0.0200(4) Uani 1 1 d . . . . . H2 H 0.6961 0.5522 0.6815 0.016(5) Uiso 1 1 calc R . . . . C3 C 0.6663(2) 0.51412(17) 0.60373(7) 0.0227(4) Uani 1 1 d . . . . . C4 C 0.5777(2) 0.4424(2) 0.57511(7) 0.0246(4) Uani 1 1 d . . . . . O4 O 0.52813(19) 0.47803(17) 0.52803(6) 0.0334(4) Uani 1 1 d . . . . . H4 H 0.564(3) 0.548(3) 0.5208(12) 0.059(10) Uiso 1 1 d . . . . . C5 C 0.51875(19) 0.3155(2) 0.59476(7) 0.0245(4) Uani 1 1 d . . . . . H5 H 0.4219 0.3308 0.6059 0.024(5) Uiso 1 1 calc R . . . . O6 O 0.59598(14) 0.27053(13) 0.63957(5) 0.0224(3) Uani 1 1 d . . . . . C11 C 0.62041(18) 0.3255(2) 0.72838(7) 0.0202(3) Uani 1 1 d . . . . . C12 C 0.6038(2) 0.1929(2) 0.73969(7) 0.0245(4) Uani 1 1 d . . . . . H12 H 0.5815 0.1331 0.7123 0.036(7) Uiso 1 1 calc R . . . . C13 C 0.6200(2) 0.1475(2) 0.79124(8) 0.0272(4) Uani 1 1 d . . . . . H13 H 0.6075 0.0572 0.7991 0.034(7) Uiso 1 1 calc R . . . . C14 C 0.6541(2) 0.2348(2) 0.83057(8) 0.0275(4) Uani 1 1 d . . . . . C15 C 0.6676(2) 0.3674(2) 0.82022(7) 0.0287(4) Uani 1 1 d . . . . . H15 H 0.6890 0.4269 0.8478 0.030(6) Uiso 1 1 calc R . . . . C16 C 0.6497(2) 0.4129(2) 0.76926(7) 0.0258(4) Uani 1 1 d . . . . . H16 H 0.6574 0.5041 0.7621 0.019(5) Uiso 1 1 calc R . . . . Br1 Br 0.68632(3) 0.17365(3) 0.90010(2) 0.04342(7) Uani 1 1 d . . . . . C21 C 0.8518(2) 0.42529(19) 0.66506(7) 0.0219(4) Uani 1 1 d . . . . . C22 C 0.9008(2) 0.3137(2) 0.63920(8) 0.0314(4) Uani 1 1 d . . . . . H22 H 0.8442 0.2696 0.6145 0.041(7) Uiso 1 1 calc R . . . . C23 C 1.0317(2) 0.2669(2) 0.64928(10) 0.0367(5) Uani 1 1 d . . . . . H23 H 1.0640 0.1899 0.6322 0.053(8) Uiso 1 1 calc R . . . . C24 C 1.1137(2) 0.3335(2) 0.68425(9) 0.0335(5) Uani 1 1 d . . . . . C25 C 1.0711(2) 0.4472(2) 0.70841(9) 0.0349(5) Uani 1 1 d . . . . . H25 H 1.1308 0.4943 0.7311 0.052(8) Uiso 1 1 calc R . . . . C26 C 0.9390(2) 0.4920(2) 0.69900(8) 0.0287(4) Uani 1 1 d . . . . . H26 H 0.9078 0.5694 0.7161 0.038(7) Uiso 1 1 calc R . . . . Cl1 Cl 1.27574(6) 0.27140(7) 0.69947(3) 0.04890(17) Uani 1 1 d . . . . . C31 C 0.7091(2) 0.64263(18) 0.58438(7) 0.0245(4) Uani 1 1 d . . . . . O31 O 0.67007(17) 0.68945(14) 0.54227(5) 0.0326(3) Uani 1 1 d . . . . . O32 O 0.79313(15) 0.70247(12) 0.61784(5) 0.0266(3) Uani 1 1 d . . . . . C33 C 0.8276(2) 0.84389(19) 0.61384(7) 0.0311(4) Uani 1 1 d . . . . . C34 C 0.9264(4) 0.8603(3) 0.65936(11) 0.0542(8) Uani 1 1 d . . . . . H34A H 0.8818 0.8330 0.6921 0.071(10) Uiso 1 1 calc R . . . . H34B H 0.9537 0.9526 0.6621 0.073(11) Uiso 1 1 calc R . . . . H34C H 1.0075 0.8059 0.6533 0.088(13) Uiso 1 1 calc R . . . . C35 C 0.8971(3) 0.8745(3) 0.56216(10) 0.0452(6) Uani 1 1 d . . . . . H35A H 0.9748 0.8149 0.5572 0.059(9) Uiso 1 1 calc R . . . . H35B H 0.9299 0.9654 0.5625 0.056(9) Uiso 1 1 calc R . . . . H35C H 0.8319 0.8629 0.5333 0.052(8) Uiso 1 1 calc R . . . . C36 C 0.6974(3) 0.9217(2) 0.62208(11) 0.0473(6) Uani 1 1 d . . . . . H36A H 0.6345 0.9053 0.5928 0.051(9) Uiso 1 1 calc R . . . . H36B H 0.7193 1.0156 0.6236 0.065(9) Uiso 1 1 calc R . . . . H36C H 0.6543 0.8948 0.6552 0.056(9) Uiso 1 1 calc R . . . . C51 C 0.5216(2) 0.20574(19) 0.55485(8) 0.0262(4) Uani 1 1 d . . . . . C52 C 0.6321(2) 0.1900(2) 0.52111(8) 0.0338(5) Uani 1 1 d . . . . . H52 H 0.7069 0.2493 0.5228 0.039(7) Uiso 1 1 calc R . . . . C53 C 0.6337(3) 0.0876(2) 0.48492(10) 0.0426(6) Uani 1 1 d . . . . . H53 H 0.7094 0.0772 0.4619 0.053(8) Uiso 1 1 calc R . . . . C54 C 0.5253(3) 0.0013(3) 0.48249(10) 0.0483(7) Uani 1 1 d . . . . . H54 H 0.5265 -0.0683 0.4576 0.056(9) Uiso 1 1 calc R . . . . C55 C 0.4149(3) 0.0153(3) 0.51601(11) 0.0462(6) Uani 1 1 d . . . . . H55 H 0.3408 -0.0448 0.5144 0.058(9) Uiso 1 1 calc R . . . . C56 C 0.4130(3) 0.1184(2) 0.55228(9) 0.0357(5) Uani 1 1 d . . . . . H56 H 0.3372 0.1286 0.5753 0.037(7) Uiso 1 1 calc R . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0240(8) 0.0178(7) 0.0196(7) -0.0006(6) -0.0021(6) -0.0005(6) C2 0.0229(10) 0.0182(8) 0.0190(7) 0.0021(6) -0.0020(7) 0.0010(7) C3 0.0288(10) 0.0195(8) 0.0199(7) 0.0025(7) -0.0005(8) 0.0064(7) C4 0.0306(11) 0.0228(9) 0.0205(9) 0.0007(7) -0.0043(8) 0.0073(8) O4 0.0491(10) 0.0280(8) 0.0232(7) 0.0021(6) -0.0129(7) 0.0056(7) C5 0.0260(9) 0.0262(9) 0.0213(8) -0.0011(8) -0.0066(7) 0.0021(8) O6 0.0290(7) 0.0184(6) 0.0197(6) -0.0016(5) -0.0053(5) 0.0020(6) C11 0.0175(8) 0.0225(9) 0.0206(7) 0.0026(7) -0.0003(6) 0.0018(8) C12 0.0251(9) 0.0214(9) 0.0269(9) 0.0015(7) -0.0017(7) -0.0007(8) C13 0.0273(10) 0.0219(10) 0.0324(10) 0.0089(8) 0.0006(8) -0.0015(8) C14 0.0255(10) 0.0360(11) 0.0209(8) 0.0090(8) -0.0006(7) -0.0015(8) C15 0.0339(11) 0.0313(10) 0.0210(8) 0.0010(7) -0.0010(8) -0.0045(9) C16 0.0333(11) 0.0207(9) 0.0233(9) 0.0022(7) -0.0005(7) -0.0014(8) Br1 0.05172(14) 0.05180(14) 0.02673(9) 0.01819(10) -0.00595(10) -0.00793(13) C21 0.0231(9) 0.0221(9) 0.0204(8) 0.0068(7) 0.0009(7) 0.0006(7) C22 0.0269(10) 0.0306(11) 0.0366(10) -0.0031(9) -0.0003(8) 0.0036(9) C23 0.0292(11) 0.0306(12) 0.0504(14) 0.0025(10) 0.0076(10) 0.0069(10) C24 0.0185(9) 0.0364(12) 0.0457(12) 0.0178(10) 0.0025(8) 0.0025(9) C25 0.0253(11) 0.0400(13) 0.0395(12) 0.0085(10) -0.0058(9) -0.0033(9) C26 0.0274(10) 0.0281(11) 0.0306(10) 0.0034(8) -0.0014(8) 0.0005(8) Cl1 0.0211(2) 0.0516(4) 0.0740(4) 0.0225(3) 0.0007(3) 0.0074(2) C31 0.0309(11) 0.0208(9) 0.0219(8) 0.0021(6) 0.0032(7) 0.0065(8) O31 0.0497(9) 0.0265(7) 0.0215(6) 0.0058(5) -0.0018(6) 0.0069(8) O32 0.0359(8) 0.0199(7) 0.0240(6) 0.0053(5) 0.0002(6) -0.0019(6) C33 0.0449(12) 0.0209(9) 0.0275(9) 0.0053(7) 0.0060(8) -0.0062(10) C34 0.075(2) 0.0398(15) 0.0480(15) 0.0096(12) -0.0114(14) -0.0276(15) C35 0.0606(17) 0.0353(13) 0.0397(13) 0.0087(10) 0.0205(13) -0.0071(12) C36 0.0625(18) 0.0276(11) 0.0517(14) -0.0015(10) 0.0155(15) 0.0075(13) C51 0.0336(11) 0.0218(10) 0.0231(9) -0.0013(7) -0.0079(8) 0.0014(8) C52 0.0418(12) 0.0277(11) 0.0321(10) -0.0029(9) 0.0005(9) -0.0013(10) C53 0.0602(17) 0.0339(13) 0.0337(12) -0.0077(10) 0.0029(11) 0.0063(12) C54 0.074(2) 0.0342(13) 0.0370(13) -0.0135(11) -0.0124(13) 0.0023(13) C55 0.0524(16) 0.0348(13) 0.0515(15) -0.0087(11) -0.0179(13) -0.0096(12) C56 0.0351(13) 0.0360(12) 0.0360(11) -0.0034(9) -0.0091(10) -0.0023(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C11 1.424(2) . ? N1 O6 1.449(2) . ? N1 C2 1.483(2) . ? C2 C3 1.511(2) . ? C2 C21 1.517(3) . ? C2 H2 1.0000 . ? C3 C4 1.347(3) . ? C3 C31 1.460(3) . ? C4 O4 1.341(2) . ? C4 C5 1.501(3) . ? O4 H4 0.82(3) . ? C5 O6 1.441(2) . ? C5 C51 1.510(3) . ? C5 H5 1.0000 . ? C11 C12 1.391(3) . ? C11 C16 1.397(3) . ? C12 C13 1.398(3) . ? C12 H12 0.9500 . ? C13 C14 1.379(3) . ? C13 H13 0.9500 . ? C14 C15 1.382(3) . ? C14 Br1 1.8997(19) . ? C15 C16 1.386(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.390(3) . ? C21 C22 1.397(3) . ? C22 C23 1.389(3) . ? C22 H22 0.9500 . ? C23 C24 1.376(4) . ? C23 H23 0.9500 . ? C24 C25 1.376(4) . ? C24 Cl1 1.749(2) . ? C25 C26 1.390(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 O31 1.232(2) . ? C31 O32 1.330(2) . ? O32 C33 1.483(2) . ? C33 C35 1.512(3) . ? C33 C36 1.514(4) . ? C33 C34 1.516(3) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C51 C56 1.387(3) . ? C51 C52 1.389(3) . ? C52 C53 1.390(3) . ? C52 H52 0.9500 . ? C53 C54 1.378(4) . ? C53 H53 0.9500 . ? C54 C55 1.382(4) . ? C54 H54 0.9500 . ? C55 C56 1.397(3) . ? C55 H55 0.9500 . ? C56 H56 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 C11 N1 O6 108.90(14) . . ? C11 N1 C2 115.77(15) . . ? O6 N1 C2 107.98(13) . . ? N1 C2 C3 107.13(15) . . ? N1 C2 C21 114.37(14) . . ? C3 C2 C21 115.18(16) . . ? N1 C2 H2 106.5 . . ? C3 C2 H2 106.5 . . ? C21 C2 H2 106.5 . . ? C4 C3 C31 119.31(17) . . ? C4 C3 C2 120.76(17) . . ? C31 C3 C2 119.33(17) . . ? O4 C4 C3 124.56(19) . . ? O4 C4 C5 113.02(18) . . ? C3 C4 C5 122.35(17) . . ? C4 O4 H4 107(2) . . ? O6 C5 C4 109.58(15) . . ? O6 C5 C51 106.60(15) . . ? C4 C5 C51 114.04(16) . . ? O6 C5 H5 108.8 . . ? C4 C5 H5 108.8 . . ? C51 C5 H5 108.8 . . ? C5 O6 N1 107.14(13) . . ? C12 C11 C16 119.25(17) . . ? C12 C11 N1 122.48(17) . . ? C16 C11 N1 118.16(17) . . ? C11 C12 C13 120.13(18) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 119.53(18) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 C15 121.03(18) . . ? C13 C14 Br1 120.16(16) . . ? C15 C14 Br1 118.80(16) . . ? C14 C15 C16 119.47(19) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C15 C16 C11 120.52(18) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C26 C21 C22 118.60(19) . . ? C26 C21 C2 119.20(18) . . ? C22 C21 C2 122.15(17) . . ? C23 C22 C21 120.6(2) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C24 C23 C22 119.1(2) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C23 C24 C25 121.8(2) . . ? C23 C24 Cl1 119.5(2) . . ? C25 C24 Cl1 118.69(19) . . ? C24 C25 C26 118.7(2) . . ? C24 C25 H25 120.6 . . ? C26 C25 H25 120.6 . . ? C21 C26 C25 121.1(2) . . ? C21 C26 H26 119.5 . . ? C25 C26 H26 119.5 . . ? O31 C31 O32 124.69(18) . . ? O31 C31 C3 123.42(19) . . ? O32 C31 C3 111.89(15) . . ? C31 O32 C33 122.79(15) . . ? O32 C33 C35 111.23(17) . . ? O32 C33 C36 107.98(19) . . ? C35 C33 C36 113.0(2) . . ? O32 C33 C34 101.51(17) . . ? C35 C33 C34 110.7(2) . . ? C36 C33 C34 111.9(2) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C56 C51 C52 119.5(2) . . ? C56 C51 C5 119.5(2) . . ? C52 C51 C5 120.98(19) . . ? C51 C52 C53 120.3(2) . . ? C51 C52 H52 119.9 . . ? C53 C52 H52 119.9 . . ? C54 C53 C52 120.0(2) . . ? C54 C53 H53 120.0 . . ? C52 C53 H53 120.0 . . ? C53 C54 C55 120.4(2) . . ? C53 C54 H54 119.8 . . ? C55 C54 H54 119.8 . . ? C54 C55 C56 119.6(3) . . ? C54 C55 H55 120.2 . . ? C56 C55 H55 120.2 . . ? C51 C56 C55 120.2(2) . . ? C51 C56 H56 119.9 . . ? C55 C56 H56 119.9 . . ? 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 C11 N1 C2 C3 179.34(15) . . . . ? O6 N1 C2 C3 57.01(17) . . . . ? C11 N1 C2 C21 50.4(2) . . . . ? O6 N1 C2 C21 -71.92(18) . . . . ? N1 C2 C3 C4 -17.9(2) . . . . ? C21 C2 C3 C4 110.5(2) . . . . ? N1 C2 C3 C31 153.11(16) . . . . ? C21 C2 C3 C31 -78.4(2) . . . . ? C31 C3 C4 O4 2.7(3) . . . . ? C2 C3 C4 O4 173.75(18) . . . . ? C31 C3 C4 C5 -174.04(18) . . . . ? C2 C3 C4 C5 -3.0(3) . . . . ? O4 C4 C5 O6 168.40(16) . . . . ? C3 C4 C5 O6 -14.5(3) . . . . ? O4 C4 C5 C51 49.0(2) . . . . ? C3 C4 C5 C51 -133.9(2) . . . . ? C4 C5 O6 N1 52.96(18) . . . . ? C51 C5 O6 N1 176.82(15) . . . . ? C11 N1 O6 C5 155.04(14) . . . . ? C2 N1 O6 C5 -78.50(17) . . . . ? O6 N1 C11 C12 -13.9(2) . . . . ? C2 N1 C11 C12 -135.75(18) . . . . ? O6 N1 C11 C16 169.94(16) . . . . ? C2 N1 C11 C16 48.1(2) . . . . ? C16 C11 C12 C13 -1.7(3) . . . . ? N1 C11 C12 C13 -177.78(18) . . . . ? C11 C12 C13 C14 -0.8(3) . . . . ? C12 C13 C14 C15 2.5(3) . . . . ? C12 C13 C14 Br1 -176.53(15) . . . . ? C13 C14 C15 C16 -1.5(3) . . . . ? Br1 C14 C15 C16 177.49(16) . . . . ? C14 C15 C16 C11 -1.1(3) . . . . ? C12 C11 C16 C15 2.6(3) . . . . ? N1 C11 C16 C15 178.90(19) . . . . ? N1 C2 C21 C26 -115.99(19) . . . . ? C3 C2 C21 C26 119.25(19) . . . . ? N1 C2 C21 C22 61.7(2) . . . . ? C3 C2 C21 C22 -63.0(2) . . . . ? C26 C21 C22 C23 3.2(3) . . . . ? C2 C21 C22 C23 -174.54(19) . . . . ? C21 C22 C23 C24 -1.4(3) . . . . ? C22 C23 C24 C25 -1.9(3) . . . . ? C22 C23 C24 Cl1 177.16(17) . . . . ? C23 C24 C25 C26 3.2(3) . . . . ? Cl1 C24 C25 C26 -175.81(17) . . . . ? C22 C21 C26 C25 -1.8(3) . . . . ? C2 C21 C26 C25 176.00(19) . . . . ? C24 C25 C26 C21 -1.3(3) . . . . ? C4 C3 C31 O31 -1.2(3) . . . . ? C2 C3 C31 O31 -172.38(18) . . . . ? C4 C3 C31 O32 178.05(18) . . . . ? C2 C3 C31 O32 6.9(2) . . . . ? O31 C31 O32 C33 13.0(3) . . . . ? C3 C31 O32 C33 -166.21(16) . . . . ? C31 O32 C33 C35 -61.1(3) . . . . ? C31 O32 C33 C36 63.4(2) . . . . ? C31 O32 C33 C34 -178.8(2) . . . . ? O6 C5 C51 C56 96.4(2) . . . . ? C4 C5 C51 C56 -142.50(19) . . . . ? O6 C5 C51 C52 -82.7(2) . . . . ? C4 C5 C51 C52 38.3(3) . . . . ? C56 C51 C52 C53 0.2(3) . . . . ? C5 C51 C52 C53 179.4(2) . . . . ? C51 C52 C53 C54 -0.1(4) . . . . ? C52 C53 C54 C55 -0.3(4) . . . . ? C53 C54 C55 C56 0.5(4) . . . . ? C52 C51 C56 C55 0.0(3) . . . . ? C5 C51 C56 C55 -179.2(2) . . . . ? C54 C55 C56 C51 -0.3(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O31 0.82(3) 1.86(3) 2.588(2) 148(3) . _refine_diff_density_max 0.380 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.041 _diffrn_radiation_monochromator graphite _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 _diffrn_orient_matrix_type standard _diffrn_orient_matrix_UB_11 -0.0981629 _diffrn_orient_matrix_UB_12 0.0126306 _diffrn_orient_matrix_UB_13 0.0098057 _diffrn_orient_matrix_UB_21 -0.0189035 _diffrn_orient_matrix_UB_22 -0.0940710 _diffrn_orient_matrix_UB_23 -0.0085552 _diffrn_orient_matrix_UB_31 0.0215570 _diffrn_orient_matrix_UB_32 -0.0250310 _diffrn_orient_matrix_UB_33 0.0371401 _diffrn_measurement_specimen_support 'MiTeGen loop' _diffrn_detector 'CCD area detector' _iucr_refine_instructions_details 'available per request' _iucr_refine_reflections_details 'available per request' _database_code_depnum_ccdc_archive 'CCDC 953542'