# 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_pn198 #?# MeasurementCode _vrf_LABEL01_pn198 ; PROBLEM: An _atom_site_label occurs more than once in the atom list. RESPONSE: identical names in different PARTs used ; _vrf_PLAT070_pn198 ; PROBLEM: Duplicate Atomic Label on INPUT ................ C11 RESPONSE: identical names in different PARTs used ; _audit_update_record 24-Jun-11 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _exptl_crystal_description platelet #?# e.g.: needle, platelet; _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 #?# in millimeters _exptl_crystal_size_mid 0.12 #?# in millimeters _exptl_crystal_size_min 0.03 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_creation_date 21-Jun-11 #?# style: 18-Aug-1998 _diffrn_ambient_temperature 173(2) #?# in K _diffrn_source_type 'FR 591 generator' _diffrn_source_power 3.025 #?# in kW _diffrn_source_voltage 55.00 #?# in kV _diffrn_source_current 55.00 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'MONTEL, graded multilayered X-ray optics' _diffrn_radiation_collimation 0.20 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD; rotation images; thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_special_details ? _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_UB_11 0.1278605 _diffrn_orient_matrix_UB_12 -0.0213931 _diffrn_orient_matrix_UB_13 0.0631853 _diffrn_orient_matrix_UB_21 -0.0066533 _diffrn_orient_matrix_UB_22 0.1244356 _diffrn_orient_matrix_UB_23 -0.0384741 _diffrn_orient_matrix_UB_31 -0.1182571 _diffrn_orient_matrix_UB_32 0.0454482 _diffrn_orient_matrix_UB_33 0.0572263 loop_ _reflns_scale_group_code _reflns_scale_meas_F 1 1.0 _cell_length_a 6.2093(4) _cell_length_b 8.3668(5) _cell_length_c 11.1450(5) _cell_angle_alpha 74.540(3) _cell_angle_beta 89.252(3) _cell_angle_gamma 68.175(3) _cell_volume 515.66(5) _cell_measurement_temperature 173(2) #?# in K _cell_measurement_reflns_used 2342 _cell_measurement_theta_min 3.134 _cell_measurement_theta_max 27.485 _cell_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 -6 0.053000 -1 3 18 0.068000 3 2 3 0.124000 -15 -6 5 0.112000 0 1 0 0.017000 0 -1 0 0.012000 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_reflns_number 4338 #xl _diffrn_reflns_av_R_equivalents 0.0410 #xl _diffrn_reflns_av_sigmaI/netI 0.0552 #xl _diffrn_reflns_limit_h_min -8 #xl _diffrn_reflns_limit_h_max 8 #xl _diffrn_reflns_limit_k_min -10 #xl _diffrn_reflns_limit_k_max 10 #xl _diffrn_reflns_limit_l_min -13 #xl _diffrn_reflns_limit_l_max 14 #xl _diffrn_reflns_theta_min 3.55 #xl _diffrn_reflns_theta_max 27.55 #xl _diffrn_measured_fraction_theta_max 0.992 #xl _diffrn_reflns_theta_full 27.55 #xl _diffrn_measured_fraction_theta_full 0.992 #xl _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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' _reflns_number_total 2364 #xl _reflns_number_gt 1540 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0579P)^2^+0.0876P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details ? #xl _refine_ls_abs_structure_Flack ? #xl _refine_ls_number_reflns 2364 #xl _refine_ls_number_parameters 200 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0882 #xl _refine_ls_R_factor_gt 0.0518 #xl _refine_ls_wR_factor_ref 0.1385 #xl _refine_ls_wR_factor_gt 0.1213 #xl _refine_ls_goodness_of_fit_ref 1.036 #xl _refine_ls_restrained_S_all 1.036 #xl _refine_ls_shift/su_max 0.000 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.178 #xl _refine_diff_density_min -0.161 #xl _refine_diff_density_rms 0.038 #xl _refine_special_details ; molecule is disordered over four sites, split model applied ; _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement ; Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. ; _computing_molecular_graphics ? _computing_publication_material ? 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 C2 C 0.5003(3) 0.8141(2) 0.81276(16) 0.0486(5) Uani 1 1 d . . . H2A H 0.3605 0.8086 0.8545 0.058 Uiso 1 1 calc R A 1 H2B H 0.5384 0.9097 0.8326 0.058 Uiso 1 1 calc R A 1 C3 C 0.4498(3) 0.8578(2) 0.67216(16) 0.0473(5) Uani 1 1 d . G . H3A H 0.2837 0.8827 0.6518 0.057 Uiso 1 1 calc R B 1 H3B H 0.4796 0.9667 0.6299 0.057 Uiso 1 1 calc R B 1 C5 C 0.5773(3) 0.52637(19) 0.69373(13) 0.0304(4) Uani 1 1 d . . . H5 H 0.4155 0.5334 0.6775 0.036 Uiso 1 1 calc R C 1 C7 C 0.7631(3) 0.1965(2) 0.70953(15) 0.0428(4) Uani 1 1 d . . . H7A H 0.6116 0.1894 0.6918 0.051 Uiso 1 1 calc R D 1 H7B H 0.8854 0.1063 0.6778 0.051 Uiso 1 1 calc R D 1 C8 C 0.8148(3) 0.1554(2) 0.84953(15) 0.0460(5) Uani 1 1 d . G . H8A H 0.9532 0.0425 0.8801 0.055 Uiso 1 1 calc R E 1 H8B H 0.6808 0.1391 0.8927 0.055 Uiso 1 1 calc R E 1 C10 C 0.6444(3) 0.48322(19) 0.83676(12) 0.0297(4) Uani 1 1 d . G . H10 H 0.5114 0.4711 0.8847 0.036 Uiso 1 1 calc R F 1 O11 O 1.0318(5) 0.7245(4) 0.8041(3) 0.0433(9) Uani 0.385(2) 1 d P G 1 C11 C 0.8926(9) 0.6694(5) 0.7789(5) 0.0327(9) Uani 0.385(2) 1 d P G 1 C12 C 0.8629(9) 0.6367(6) 0.6540(4) 0.0314(9) Uani 0.385(2) 1 d P G 1 H12 H 0.9345 0.7019 0.5876 0.038 Uiso 0.385(2) 1 calc PR G 1 C13 C 0.9644(10) 0.4269(6) 0.6679(5) 0.0320(10) Uani 0.385(2) 1 d P G 1 H13 H 1.0834 0.3952 0.6079 0.038 Uiso 0.385(2) 1 calc PR G 1 C14 C 1.0616(12) 0.3174(6) 0.8024(7) 0.0360(12) Uani 0.385(2) 1 d P G 1 H14A H 1.1695 0.1948 0.8042 0.043 Uiso 0.385(2) 1 calc PR G 1 H14B H 1.1491 0.3745 0.8380 0.043 Uiso 0.385(2) 1 calc PR G 1 C1 C 0.7041(3) 0.6346(2) 0.86092(13) 0.0333(4) Uani 0.385(2) 1 d P G 1 H1 H 0.7515 0.6093 0.9516 0.040 Uiso 0.385(2) 1 calc PR G 1 C4 C 0.6027(3) 0.7021(2) 0.62507(13) 0.0338(4) Uani 0.385(2) 1 d P G 1 H4 H 0.5637 0.7299 0.5331 0.041 Uiso 0.385(2) 1 calc PR G 1 C6 C 0.7551(3) 0.3830(2) 0.64315(13) 0.0306(4) Uani 0.385(2) 1 d P G 1 H6 H 0.7177 0.4105 0.5511 0.037 Uiso 0.385(2) 1 calc PR G 1 C9 C 0.8598(3) 0.3084(2) 0.87934(13) 0.0328(4) Uani 0.385(2) 1 d P G 1 H9 H 0.9067 0.2786 0.9706 0.039 Uiso 0.385(2) 1 calc PR G 1 O14 O 1.2627(7) 0.2448(6) 0.8424(4) 0.0407(12) Uani 0.2463(15) 1 d P G 2 C11 C 0.8926(9) 0.6694(5) 0.7789(5) 0.0327(9) Uani 0.2463(15) 1 d P G 2 H11A H 0.8785 0.7948 0.7657 0.039 Uiso 0.2463(15) 1 calc PR G 2 H11B H 1.0493 0.5885 0.8213 0.039 Uiso 0.2463(15) 1 calc PR G 2 C12 C 0.8629(9) 0.6367(6) 0.6540(4) 0.0314(9) Uani 0.2463(15) 1 d P G 2 H12A H 0.9345 0.7019 0.5876 0.038 Uiso 0.2463(15) 1 calc PR G 2 C13 C 0.9644(10) 0.4269(6) 0.6679(5) 0.0320(10) Uani 0.2463(15) 1 d P G 2 H13A H 1.0834 0.3952 0.6079 0.038 Uiso 0.2463(15) 1 calc PR G 2 C14 C 1.0616(12) 0.3174(6) 0.8024(7) 0.0360(12) Uani 0.2463(15) 1 d P G 2 C1 C 0.7041(3) 0.6346(2) 0.86092(13) 0.0333(4) Uani 0.2463(15) 1 d P G 2 H1A H 0.7515 0.6093 0.9516 0.040 Uiso 0.2463(15) 1 calc PR G 2 C4 C 0.6027(3) 0.7021(2) 0.62507(13) 0.0338(4) Uani 0.2463(15) 1 d P G 2 H4A H 0.5637 0.7299 0.5331 0.041 Uiso 0.2463(15) 1 calc PR G 2 C6 C 0.7551(3) 0.3830(2) 0.64315(13) 0.0306(4) Uani 0.2463(15) 1 d P G 2 H6A H 0.7177 0.4105 0.5511 0.037 Uiso 0.2463(15) 1 calc PR G 2 C9 C 0.8598(3) 0.3084(2) 0.87934(13) 0.0328(4) Uani 0.2463(15) 1 d P G 2 H9A H 0.9067 0.2786 0.9706 0.039 Uiso 0.2463(15) 1 calc PR G 2 O121 O 0.9513(7) 0.7862(6) 0.5948(3) 0.0447(13) Uani 0.284(3) 1 d P G 3 C111 C 0.9307(15) 0.5936(10) 0.7966(8) 0.0328(17) Uani 0.284(3) 1 d P G 3 H11C H 1.0462 0.6277 0.8345 0.039 Uiso 0.284(3) 1 calc PR G 3 C121 C 0.8531(16) 0.7007(11) 0.6640(8) 0.0326(16) Uani 0.284(3) 1 d P G 3 C131 C 1.0158(18) 0.3558(11) 0.6766(10) 0.037(2) Uani 0.284(3) 1 d P G 3 H13C H 1.1226 0.2335 0.6770 0.045 Uiso 0.284(3) 1 calc PR G 3 H13B H 1.0602 0.4436 0.6135 0.045 Uiso 0.284(3) 1 calc PR G 3 C141 C 1.0333(17) 0.3824(11) 0.8040(10) 0.0286(17) Uani 0.284(3) 1 d P G 3 H14C H 1.1960 0.3192 0.8457 0.034 Uiso 0.284(3) 1 calc PR G 3 C1 C 0.7041(3) 0.6346(2) 0.86092(13) 0.0333(4) Uani 0.284(3) 1 d P G 3 H1B H 0.7414 0.6094 0.9527 0.040 Uiso 0.284(3) 1 calc PR G 3 C4 C 0.6027(3) 0.7021(2) 0.62507(13) 0.0338(4) Uani 0.284(3) 1 d P G 3 H4B H 0.5736 0.7294 0.5324 0.041 Uiso 0.284(3) 1 calc PR G 3 C6 C 0.7551(3) 0.3830(2) 0.64315(13) 0.0306(4) Uani 0.284(3) 1 d P G 3 H6B H 0.7211 0.4108 0.5508 0.037 Uiso 0.284(3) 1 calc PR G 3 C9 C 0.8598(3) 0.3084(2) 0.87934(13) 0.0328(4) Uani 0.284(3) 1 d P G 3 H9B H 0.9020 0.2784 0.9712 0.039 Uiso 0.284(3) 1 calc PR G 3 O131 O 1.178(2) 0.3035(17) 0.6310(10) 0.044(3) Uani 0.0848(9) 1 d P G 4 C111 C 0.9307(15) 0.5936(10) 0.7966(8) 0.0328(17) Uani 0.0848(9) 1 d P G 4 H11D H 1.0462 0.6277 0.8345 0.039 Uiso 0.0848(9) 1 calc PR G 4 C121 C 0.8531(16) 0.7007(11) 0.6640(8) 0.0326(16) Uani 0.0848(9) 1 d P G 4 H12C H 0.9687 0.6479 0.6092 0.039 Uiso 0.0848(9) 1 calc PR G 4 H12B H 0.8410 0.8251 0.6534 0.039 Uiso 0.0848(9) 1 calc PR G 4 C131 C 1.0158(18) 0.3558(11) 0.6766(10) 0.037(2) Uani 0.0848(9) 1 d P G 4 C141 C 1.0333(17) 0.3824(11) 0.8040(10) 0.0286(17) Uani 0.0848(9) 1 d P G 4 H14D H 1.1960 0.3192 0.8457 0.034 Uiso 0.0848(9) 1 calc PR G 4 C1 C 0.7041(3) 0.6346(2) 0.86092(13) 0.0333(4) Uani 0.0848(9) 1 d P G 4 H1C H 0.7414 0.6094 0.9527 0.040 Uiso 0.0848(9) 1 calc PR G 4 C4 C 0.6027(3) 0.7021(2) 0.62507(13) 0.0338(4) Uani 0.0848(9) 1 d P G 4 H4C H 0.5736 0.7294 0.5324 0.041 Uiso 0.0848(9) 1 calc PR G 4 C6 C 0.7551(3) 0.3830(2) 0.64315(13) 0.0306(4) Uani 0.0848(9) 1 d P G 4 H6C H 0.7211 0.4108 0.5508 0.037 Uiso 0.0848(9) 1 calc PR G 4 C9 C 0.8598(3) 0.3084(2) 0.87934(13) 0.0328(4) Uani 0.0848(9) 1 d P G 4 H9C H 0.9020 0.2784 0.9712 0.039 Uiso 0.0848(9) 1 calc PR G 4 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 C2 0.0540(11) 0.0377(10) 0.0570(11) -0.0226(8) 0.0195(9) -0.0147(9) C3 0.0405(10) 0.0314(9) 0.0620(11) -0.0102(8) -0.0056(8) -0.0068(8) C5 0.0283(8) 0.0294(8) 0.0317(8) -0.0079(6) -0.0029(6) -0.0095(7) C7 0.0540(11) 0.0337(9) 0.0437(9) -0.0128(7) -0.0028(8) -0.0185(8) C8 0.0642(12) 0.0313(9) 0.0413(9) -0.0048(7) -0.0014(8) -0.0204(9) C10 0.0317(8) 0.0328(8) 0.0274(7) -0.0085(6) 0.0070(6) -0.0157(7) O11 0.0421(18) 0.055(2) 0.0482(18) -0.0228(14) 0.0071(13) -0.0297(16) C11 0.030(2) 0.032(2) 0.034(2) -0.006(2) 0.0017(14) -0.012(2) C12 0.0365(17) 0.042(3) 0.0250(15) -0.0125(16) 0.0071(11) -0.023(2) C13 0.026(3) 0.042(3) 0.0293(18) -0.012(2) 0.0061(16) -0.013(2) C14 0.039(2) 0.030(3) 0.0401(18) -0.013(2) -0.0042(14) -0.012(2) C1 0.0350(9) 0.0398(9) 0.0305(8) -0.0155(7) 0.0068(6) -0.0165(7) C4 0.0321(8) 0.0330(9) 0.0299(8) -0.0026(6) -0.0005(6) -0.0093(7) C6 0.0356(8) 0.0334(9) 0.0255(7) -0.0095(6) 0.0003(6) -0.0151(7) C9 0.0383(9) 0.0339(9) 0.0247(7) -0.0038(6) -0.0035(6) -0.0151(7) O14 0.022(2) 0.038(3) 0.054(3) -0.012(2) -0.012(2) -0.002(2) C11 0.030(2) 0.032(2) 0.034(2) -0.006(2) 0.0017(14) -0.012(2) C12 0.0365(17) 0.042(3) 0.0250(15) -0.0125(16) 0.0071(11) -0.023(2) C13 0.026(3) 0.042(3) 0.0293(18) -0.012(2) 0.0061(16) -0.013(2) C14 0.039(2) 0.030(3) 0.0401(18) -0.013(2) -0.0042(14) -0.012(2) C1 0.0350(9) 0.0398(9) 0.0305(8) -0.0155(7) 0.0068(6) -0.0165(7) C4 0.0321(8) 0.0330(9) 0.0299(8) -0.0026(6) -0.0005(6) -0.0093(7) C6 0.0356(8) 0.0334(9) 0.0255(7) -0.0095(6) 0.0003(6) -0.0151(7) C9 0.0383(9) 0.0339(9) 0.0247(7) -0.0038(6) -0.0035(6) -0.0151(7) O121 0.046(3) 0.052(3) 0.045(2) -0.0088(19) 0.0134(19) -0.032(2) C111 0.031(4) 0.045(5) 0.024(3) -0.007(4) 0.002(2) -0.018(4) C121 0.030(3) 0.043(5) 0.037(3) -0.022(3) 0.006(2) -0.020(4) C131 0.028(5) 0.037(5) 0.040(3) -0.007(4) -0.002(3) -0.008(4) C141 0.021(3) 0.037(5) 0.033(3) -0.013(4) 0.000(2) -0.015(4) C1 0.0350(9) 0.0398(9) 0.0305(8) -0.0155(7) 0.0068(6) -0.0165(7) C4 0.0321(8) 0.0330(9) 0.0299(8) -0.0026(6) -0.0005(6) -0.0093(7) C6 0.0356(8) 0.0334(9) 0.0255(7) -0.0095(6) 0.0003(6) -0.0151(7) C9 0.0383(9) 0.0339(9) 0.0247(7) -0.0038(6) -0.0035(6) -0.0151(7) O131 0.031(7) 0.054(9) 0.032(7) -0.016(6) 0.014(6) 0.003(6) C111 0.031(4) 0.045(5) 0.024(3) -0.007(4) 0.002(2) -0.018(4) C121 0.030(3) 0.043(5) 0.037(3) -0.022(3) 0.006(2) -0.020(4) C131 0.028(5) 0.037(5) 0.040(3) -0.007(4) -0.002(3) -0.008(4) C141 0.021(3) 0.037(5) 0.033(3) -0.013(4) 0.000(2) -0.015(4) C1 0.0350(9) 0.0398(9) 0.0305(8) -0.0155(7) 0.0068(6) -0.0165(7) C4 0.0321(8) 0.0330(9) 0.0299(8) -0.0026(6) -0.0005(6) -0.0093(7) C6 0.0356(8) 0.0334(9) 0.0255(7) -0.0095(6) 0.0003(6) -0.0151(7) C9 0.0383(9) 0.0339(9) 0.0247(7) -0.0038(6) -0.0035(6) -0.0151(7) 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 C2 C3 1.520(2) . ? C2 C1 1.523(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.519(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 C6 1.528(2) . ? C5 C4 1.530(2) . ? C5 C10 1.5632(19) . ? C5 H5 1.0000 . ? C7 C8 1.517(2) . ? C7 C6 1.521(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.524(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C10 C9 1.532(2) . ? C10 C1 1.532(2) . ? C10 H10 1.0000 . ? O11 C11 1.187(6) . ? C11 C12 1.515(7) . ? C11 C1 1.541(6) . ? C12 C4 1.509(5) . ? C12 C13 1.592(7) . ? C12 H12 1.0000 . ? C13 C6 1.523(7) . ? C13 C14 1.526(9) . ? C13 H13 1.0000 . ? C14 C9 1.523(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C1 H1 1.0000 . ? C4 H4 1.0000 . ? C6 H6 1.0000 . ? C9 H9 1.0000 . ? O121 C121 1.223(9) . ? C111 C121 1.486(12) . ? C111 C141 1.619(12) . ? C111 H11C 1.0000 . ? C131 C141 1.506(15) . ? C131 H13C 0.9900 . ? C131 H13B 0.9900 . ? C141 H14C 1.0000 . ? 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 C3 C2 C1 109.91(13) . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C4 C3 C2 110.41(13) . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C6 C5 C4 105.20(12) . . ? C6 C5 C10 108.93(11) . . ? C4 C5 C10 109.06(11) . . ? C6 C5 H5 111.2 . . ? C4 C5 H5 111.2 . . ? C10 C5 H5 111.2 . . ? C8 C7 C6 110.32(13) . . ? C8 C7 H7A 109.6 . . ? C6 C7 H7A 109.6 . . ? C8 C7 H7B 109.6 . . ? C6 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C7 C8 C9 110.10(12) . . ? C7 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.2 . . ? C9 C10 C1 108.34(12) . . ? C9 C10 C5 109.49(12) . . ? C1 C10 C5 109.37(11) . . ? C9 C10 H10 109.9 . . ? C1 C10 H10 109.9 . . ? C5 C10 H10 109.9 . . ? O11 C11 C12 124.0(5) . . ? O11 C11 C1 126.4(5) . . ? C12 C11 C1 109.4(4) . . ? C4 C12 C11 104.6(3) . . ? C4 C12 C13 106.4(3) . . ? C11 C12 C13 110.2(4) . . ? C4 C12 H12 111.8 . . ? C11 C12 H12 111.8 . . ? C13 C12 H12 111.8 . . ? C6 C13 C14 105.1(4) . . ? C6 C13 C12 105.6(4) . . ? C14 C13 C12 111.4(4) . . ? C6 C13 H13 111.4 . . ? C14 C13 H13 111.4 . . ? C12 C13 H13 111.4 . . ? C9 C14 C13 108.9(5) . . ? C9 C14 H14A 109.9 . . ? C13 C14 H14A 109.9 . . ? C9 C14 H14B 109.9 . . ? C13 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? C2 C1 C10 110.54(13) . . ? C2 C1 C11 100.72(19) . . ? C10 C1 C11 111.4(2) . . ? C2 C1 H1 111.3 . . ? C10 C1 H1 111.3 . . ? C11 C1 H1 111.3 . . ? C12 C4 C3 117.53(19) . . ? C12 C4 C5 96.9(2) . . ? C3 C4 C5 112.05(13) . . ? C12 C4 H4 109.9 . . ? C3 C4 H4 109.9 . . ? C5 C4 H4 109.9 . . ? C7 C6 C13 117.8(2) . . ? C7 C6 C5 111.59(13) . . ? C13 C6 C5 96.4(2) . . ? C7 C6 H6 110.1 . . ? C13 C6 H6 110.1 . . ? C5 C6 H6 110.1 . . ? C14 C9 C8 102.0(2) . . ? C14 C9 C10 111.4(2) . . ? C8 C9 C10 110.48(13) . . ? C14 C9 H9 110.9 . . ? C8 C9 H9 110.9 . . ? C10 C9 H9 110.9 . . ? C121 C111 C141 108.9(8) . . ? C121 C111 H11C 111.9 . . ? C141 C111 H11C 111.9 . . ? O121 C121 C111 126.8(7) . . ? C141 C131 H13C 110.1 . . ? C141 C131 H13B 110.1 . . ? H13C C131 H13B 108.4 . . ? C131 C141 C111 111.1(8) . . ? C131 C141 H14C 111.9 . . ? C111 C141 H14C 111.9 . . ? 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 C1 C2 C3 C4 5.2(2) . . . . ? C6 C7 C8 C9 -4.0(2) . . . . ? C6 C5 C10 C9 -2.14(15) . . . . ? C4 C5 C10 C9 -116.45(13) . . . . ? C6 C5 C10 C1 116.43(13) . . . . ? C4 C5 C10 C1 2.12(16) . . . . ? O11 C11 C12 C4 -139.4(4) . . . . ? C1 C11 C12 C4 36.2(4) . . . . ? O11 C11 C12 C13 106.6(5) . . . . ? C1 C11 C12 C13 -77.8(5) . . . . ? C4 C12 C13 C6 1.2(5) . . . . ? C11 C12 C13 C6 114.0(4) . . . . ? C4 C12 C13 C14 -112.5(5) . . . . ? C11 C12 C13 C14 0.4(6) . . . . ? C6 C13 C14 C9 -35.0(4) . . . . ? C12 C13 C14 C9 78.9(5) . . . . ? C3 C2 C1 C10 -62.03(17) . . . . ? C3 C2 C1 C11 55.8(3) . . . . ? C9 C10 C1 C2 176.50(11) . . . . ? C5 C10 C1 C2 57.22(16) . . . . ? C9 C10 C1 C11 65.4(2) . . . . ? C5 C10 C1 C11 -53.9(2) . . . . ? O11 C11 C1 C2 92.0(4) . . . . ? C12 C11 C1 C2 -83.5(3) . . . . ? O11 C11 C1 C10 -150.7(4) . . . . ? C12 C11 C1 C10 33.8(4) . . . . ? C11 C12 C4 C3 31.8(4) . . . . ? C13 C12 C4 C3 148.4(3) . . . . ? C11 C12 C4 C5 -87.5(3) . . . . ? C13 C12 C4 C5 29.1(3) . . . . ? C2 C3 C4 C12 -55.8(3) . . . . ? C2 C3 C4 C5 55.18(18) . . . . ? C6 C5 C4 C12 -52.1(2) . . . . ? C10 C5 C4 C12 64.7(2) . . . . ? C6 C5 C4 C3 -175.52(11) . . . . ? C10 C5 C4 C3 -58.81(16) . . . . ? C8 C7 C6 C13 53.9(3) . . . . ? C8 C7 C6 C5 -56.32(18) . . . . ? C14 C13 C6 C7 -31.6(5) . . . . ? C12 C13 C6 C7 -149.5(3) . . . . ? C14 C13 C6 C5 87.0(4) . . . . ? C12 C13 C6 C5 -30.9(4) . . . . ? C4 C5 C6 C7 176.03(11) . . . . ? C10 C5 C6 C7 59.23(15) . . . . ? C4 C5 C6 C13 52.7(2) . . . . ? C10 C5 C6 C13 -64.1(2) . . . . ? C13 C14 C9 C8 82.5(3) . . . . ? C13 C14 C9 C10 -35.4(4) . . . . ? C7 C8 C9 C14 -57.3(3) . . . . ? C7 C8 C9 C10 61.24(18) . . . . ? C1 C10 C9 C14 -63.7(3) . . . . ? C5 C10 C9 C14 55.5(3) . . . . ? C1 C10 C9 C8 -176.31(11) . . . . ? C5 C10 C9 C8 -57.11(15) . . . . ? C141 C111 C121 O121 -105.9(9) . . . . ? C121 C111 C141 C131 -1.3(10) . . . . ? _audit_block_code C14H18O_pn198_trauner _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C14 H18 O' _chemical_formula_sum 'C14 H18 O' _chemical_formula_weight 202.292 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 2 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.30287(13) _exptl_crystal_F_000 220 _database_code_depnum_ccdc_archive 'CCDC 948941' ####################################################################### # # 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_qn045 #?# MeasurementCode _vrf_STRVA01_qn045 ; PROBLEM: Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.400 From the CIF: _refine_ls_abs_structure_Flack_su 0.070 RESPONSE: refined as racemic twin, volume ratio 0.4/0.6 ; _vrf_PLAT033_qn045 ; PROBLEM: Flack x Parameter Value Deviates from Zero ..... 0.400 RESPONSE: refined as racemic twin, volume ratio 0.4/0.6 ; _vrf_REFLT03_qn045 ; PROBLEM: Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.43 From the CIF: _reflns_number_total 3189 Count of symmetry unique reflns 1839 Completeness (_total/calc) 173.41% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1350 Fraction of Friedel pairs measured 0.734 Are heavy atom types Z>Si present yes RESPONSE: 1354 Friedel pairs measured ; _audit_update_record 27-Jan-12 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _chemical_absolute_configuration ad _exptl_crystal_description block #?# e.g.: needle, platelet; pr _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 #?# in millimeters _exptl_crystal_size_mid 0.09 #?# in millimeters _exptl_crystal_size_min 0.06 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_creation_date 27-Jan-12 #?# style: 18-Aug-1998 _diffrn_ambient_temperature 173(2) #?# in K _diffrn_source_type 'FR 591 generator' _diffrn_source_power 3.025 #?# in kW _diffrn_source_voltage 55.00 #?# in kV _diffrn_source_current 55.00 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'MONTEL, graded multilayered X-ray optics' _diffrn_radiation_collimation 0.20 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD; rotation images; thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_special_details ? _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_UB_11 0.0071077 _diffrn_orient_matrix_UB_12 0.0778977 _diffrn_orient_matrix_UB_13 0.0237144 _diffrn_orient_matrix_UB_21 0.0845686 _diffrn_orient_matrix_UB_22 -0.0203764 _diffrn_orient_matrix_UB_23 0.0474266 _diffrn_orient_matrix_UB_31 0.0744892 _diffrn_orient_matrix_UB_32 0.0157007 _diffrn_orient_matrix_UB_33 -0.0561068 loop_ _reflns_scale_group_code _reflns_scale_meas_F 1 1.0 _cell_length_a 8.8558(2) _cell_length_b 12.1899(3) _cell_length_c 12.9536(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1398.36(6) _cell_measurement_temperature 173(2) #?# in K _cell_measurement_reflns_used 5578 _cell_measurement_theta_min 3.134 _cell_measurement_theta_max 27.485 _cell_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 -1 0.067000 0 0 1 0.094000 -6 0 -1 0.043000 1 0 0 0.045000 0 1 0 0.019000 0 -1 0 0.036000 _exptl_absorpt_coefficient_mu 0.834 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_reflns_number 11150 #xl _diffrn_reflns_av_R_equivalents 0.0297 #xl _diffrn_reflns_av_sigmaI/netI 0.0279 #xl _diffrn_reflns_limit_h_min -11 #xl _diffrn_reflns_limit_h_max 11 #xl _diffrn_reflns_limit_k_min -15 #xl _diffrn_reflns_limit_k_max 15 #xl _diffrn_reflns_limit_l_min -16 #xl _diffrn_reflns_limit_l_max 16 #xl _diffrn_reflns_theta_min 3.15 #xl _diffrn_reflns_theta_max 27.43 #xl _diffrn_measured_fraction_theta_max 0.997 #xl _diffrn_reflns_theta_full 27.43 #xl _diffrn_measured_fraction_theta_full 0.997 #xl _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _reflns_number_total 3189 #xl _reflns_number_gt 2936 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0313P)^2^+0.5754P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' #xl _refine_ls_abs_structure_Flack 0.40(7) #xl _refine_ls_number_reflns 3189 #xl _refine_ls_number_parameters 173 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0352 #xl _refine_ls_R_factor_gt 0.0302 #xl _refine_ls_wR_factor_ref 0.0720 #xl _refine_ls_wR_factor_gt 0.0692 #xl _refine_ls_goodness_of_fit_ref 1.065 #xl _refine_ls_restrained_S_all 1.065 #xl _refine_ls_shift/su_max 0.001 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.380 #xl _refine_diff_density_min -0.271 #xl _refine_diff_density_rms 0.054 #xl _refine_special_details ; refined as racemic twin, volume ratio 0.4/0.6 ; _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement ; Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. ; _computing_molecular_graphics ? _computing_publication_material ? 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 Cl1 Cl 1.03466(6) 0.96143(4) 0.71753(3) 0.02738(13) Uani 1 1 d . . . Cl2 Cl 0.92553(8) 0.75113(5) 0.83677(5) 0.04186(16) Uani 1 1 d . . . Cl3 Cl 0.92966(8) 0.75934(5) 1.08541(5) 0.04103(16) Uani 1 1 d . . . Cl4 Cl 1.04186(7) 0.97658(5) 1.19024(4) 0.03093(13) Uani 1 1 d . . . O1 O 0.54789(16) 1.01561(13) 0.95168(13) 0.0358(4) Uani 1 1 d . . . C1 C 1.0347(2) 0.96902(16) 0.85553(14) 0.0199(4) Uani 1 1 d . . . C2 C 0.9792(2) 0.86459(17) 0.90587(17) 0.0225(4) Uani 1 1 d . . . C3 C 0.9808(2) 0.86764(17) 1.00850(16) 0.0233(4) Uani 1 1 d . . . C4 C 1.0382(2) 0.97497(16) 1.05223(14) 0.0201(4) Uani 1 1 d . . . C5 C 1.2009(2) 0.9904(2) 1.01166(16) 0.0250(5) Uani 1 1 d . . . H5A H 1.2419 1.0614 1.0361 0.030 Uiso 1 1 calc R . . H5B H 1.2665 0.9310 1.0381 0.030 Uiso 1 1 calc R . . C6 C 1.1984(2) 0.9881(2) 0.89256(16) 0.0237(5) Uani 1 1 d . . . H6A H 1.2645 0.9285 0.8670 0.028 Uiso 1 1 calc R . . H6B H 1.2367 1.0586 0.8650 0.028 Uiso 1 1 calc R . . C7 C 0.9406(2) 1.06914(15) 0.89135(14) 0.0185(4) Uani 1 1 d . . . H7 H 0.9953 1.1363 0.8676 0.022 Uiso 1 1 calc R . . C8 C 0.9408(2) 1.07141(16) 1.01233(14) 0.0199(4) Uani 1 1 d . . . H8 H 0.9929 1.1406 1.0336 0.024 Uiso 1 1 calc R . . C9 C 0.7762(2) 1.07919(17) 1.05182(18) 0.0246(4) Uani 1 1 d . . . H9 H 0.7741 1.0778 1.1290 0.030 Uiso 1 1 calc R . . C10 C 0.7128(3) 1.1886(2) 1.01153(18) 0.0334(6) Uani 1 1 d . . . H10A H 0.7750 1.2501 1.0376 0.040 Uiso 1 1 calc R . . H10B H 0.6082 1.1988 1.0367 0.040 Uiso 1 1 calc R . . C11 C 0.7144(3) 1.1881(2) 0.89134(18) 0.0313(5) Uani 1 1 d . . . H11A H 0.6106 1.1993 0.8650 0.038 Uiso 1 1 calc R . . H11B H 0.7782 1.2490 0.8658 0.038 Uiso 1 1 calc R . . C12 C 0.7764(2) 1.07834(18) 0.85122(17) 0.0234(4) Uani 1 1 d . . . H12 H 0.7744 1.0766 0.7741 0.028 Uiso 1 1 calc R . . C13 C 0.6834(2) 0.9846(2) 0.89546(18) 0.0273(5) Uani 1 1 d . . . H13 H 0.6850 0.9123 0.8591 0.033 Uiso 1 1 calc R . . C14 C 0.6836(2) 0.9854(2) 1.00861(18) 0.0264(5) Uani 1 1 d . . . H14 H 0.6850 0.9135 1.0458 0.032 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 Cl1 0.0282(3) 0.0376(3) 0.0164(2) -0.0017(2) 0.0012(2) 0.0038(2) Cl2 0.0634(4) 0.0241(3) 0.0381(3) -0.0105(2) 0.0031(3) -0.0080(3) Cl3 0.0572(4) 0.0269(3) 0.0390(3) 0.0139(2) 0.0037(3) -0.0050(3) Cl4 0.0285(3) 0.0484(3) 0.0160(2) 0.0021(2) -0.0013(2) -0.0009(3) O1 0.0165(7) 0.0495(9) 0.0414(8) 0.0053(9) 0.0020(8) 0.0021(7) C1 0.0187(9) 0.0233(10) 0.0178(8) 0.0003(8) 0.0004(8) 0.0010(9) C2 0.0229(10) 0.0175(9) 0.0272(9) -0.0023(8) 0.0003(9) 0.0023(8) C3 0.0226(10) 0.0212(10) 0.0261(9) 0.0056(8) 0.0010(8) 0.0027(9) C4 0.0196(9) 0.0273(10) 0.0135(8) 0.0010(8) 0.0000(9) 0.0003(9) C5 0.0199(10) 0.0352(14) 0.0200(10) 0.0015(9) -0.0010(8) 0.0000(9) C6 0.0178(10) 0.0322(12) 0.0211(10) 0.0004(9) 0.0018(8) 0.0014(9) C7 0.0196(10) 0.0164(9) 0.0195(9) 0.0021(7) 0.0020(8) -0.0010(8) C8 0.0228(10) 0.0180(9) 0.0190(9) -0.0013(7) 0.0016(8) -0.0015(8) C9 0.0244(10) 0.0281(11) 0.0213(10) -0.0001(9) 0.0057(10) 0.0045(8) C10 0.0371(13) 0.0289(13) 0.0342(13) -0.0015(10) 0.0056(10) 0.0114(11) C11 0.0324(13) 0.0294(12) 0.0320(12) 0.0044(10) 0.0008(10) 0.0108(10) C12 0.0206(10) 0.0272(11) 0.0223(10) 0.0016(9) -0.0022(9) 0.0050(9) C13 0.0190(10) 0.0303(12) 0.0327(12) -0.0012(10) -0.0023(9) 0.0019(9) C14 0.0167(10) 0.0302(13) 0.0324(12) 0.0039(10) 0.0028(8) 0.0012(9) 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 Cl1 C1 1.7900(19) . ? Cl2 C2 1.715(2) . ? Cl3 C3 1.715(2) . ? Cl4 C4 1.7881(19) . ? O1 C13 1.453(3) . ? O1 C14 1.457(3) . ? C1 C2 1.512(3) . ? C1 C6 1.545(3) . ? C1 C7 1.549(3) . ? C2 C3 1.330(3) . ? C3 C4 1.514(3) . ? C4 C5 1.545(3) . ? C4 C8 1.547(3) . ? C5 C6 1.543(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C12 1.548(3) . ? C7 C8 1.567(2) . ? C7 H7 1.0000 . ? C8 C9 1.547(3) . ? C8 H8 1.0000 . ? C9 C14 1.514(3) . ? C9 C10 1.538(3) . ? C9 H9 1.0000 . ? C10 C11 1.557(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.537(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.521(3) . ? C12 H12 1.0000 . ? C13 C14 1.466(3) . ? C13 H13 1.0000 . ? C14 H14 1.0000 . ? 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 C13 O1 C14 60.48(12) . . ? C2 C1 C6 107.33(17) . . ? C2 C1 C7 111.06(15) . . ? C6 C1 C7 107.05(16) . . ? C2 C1 Cl1 112.78(14) . . ? C6 C1 Cl1 108.53(14) . . ? C7 C1 Cl1 109.87(13) . . ? C3 C2 C1 113.84(19) . . ? C3 C2 Cl2 123.18(18) . . ? C1 C2 Cl2 122.95(15) . . ? C2 C3 C4 113.69(19) . . ? C2 C3 Cl3 123.81(18) . . ? C4 C3 Cl3 122.46(15) . . ? C3 C4 C5 106.94(17) . . ? C3 C4 C8 110.16(15) . . ? C5 C4 C8 108.27(16) . . ? C3 C4 Cl4 112.94(14) . . ? C5 C4 Cl4 108.76(13) . . ? C8 C4 Cl4 109.62(13) . . ? C6 C5 C4 108.94(17) . . ? C6 C5 H5A 109.9 . . ? C4 C5 H5A 109.9 . . ? C6 C5 H5B 109.9 . . ? C4 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? C5 C6 C1 109.04(17) . . ? C5 C6 H6A 109.9 . . ? C1 C6 H6A 109.9 . . ? C5 C6 H6B 109.9 . . ? C1 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? C12 C7 C1 117.51(16) . . ? C12 C7 C8 109.61(18) . . ? C1 C7 C8 108.23(16) . . ? C12 C7 H7 107.0 . . ? C1 C7 H7 107.0 . . ? C8 C7 H7 107.0 . . ? C4 C8 C9 117.47(16) . . ? C4 C8 C7 108.74(16) . . ? C9 C8 C7 109.30(18) . . ? C4 C8 H8 106.9 . . ? C9 C8 H8 106.9 . . ? C7 C8 H8 106.9 . . ? C14 C9 C10 109.34(19) . . ? C14 C9 C8 109.99(17) . . ? C10 C9 C8 106.54(17) . . ? C14 C9 H9 110.3 . . ? C10 C9 H9 110.3 . . ? C8 C9 H9 110.3 . . ? C9 C10 C11 109.4(2) . . ? C9 C10 H10A 109.8 . . ? C11 C10 H10A 109.8 . . ? C9 C10 H10B 109.8 . . ? C11 C10 H10B 109.8 . . ? H10A C10 H10B 108.2 . . ? C12 C11 C10 110.15(19) . . ? C12 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? C12 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C13 C12 C11 109.44(18) . . ? C13 C12 C7 109.14(16) . . ? C11 C12 C7 106.58(18) . . ? C13 C12 H12 110.5 . . ? C11 C12 H12 110.5 . . ? C7 C12 H12 110.5 . . ? O1 C13 C14 59.88(14) . . ? O1 C13 C12 116.16(19) . . ? C14 C13 C12 111.8(2) . . ? O1 C13 H13 118.5 . . ? C14 C13 H13 118.5 . . ? C12 C13 H13 118.5 . . ? O1 C14 C13 59.64(14) . . ? O1 C14 C9 116.31(19) . . ? C13 C14 C9 112.0(2) . . ? O1 C14 H14 118.4 . . ? C13 C14 H14 118.4 . . ? C9 C14 H14 118.4 . . ? 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 C6 C1 C2 C3 59.4(2) . . . . ? C7 C1 C2 C3 -57.3(3) . . . . ? Cl1 C1 C2 C3 178.86(17) . . . . ? C6 C1 C2 Cl2 -118.47(18) . . . . ? C7 C1 C2 Cl2 124.83(17) . . . . ? Cl1 C1 C2 Cl2 1.0(2) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? Cl2 C2 C3 C4 177.70(14) . . . . ? C1 C2 C3 Cl3 -177.87(14) . . . . ? Cl2 C2 C3 Cl3 0.0(3) . . . . ? C2 C3 C4 C5 -59.6(2) . . . . ? Cl3 C3 C4 C5 118.19(18) . . . . ? C2 C3 C4 C8 57.9(2) . . . . ? Cl3 C3 C4 C8 -124.36(16) . . . . ? C2 C3 C4 Cl4 -179.17(17) . . . . ? Cl3 C3 C4 Cl4 -1.4(2) . . . . ? C3 C4 C5 C6 57.3(2) . . . . ? C8 C4 C5 C6 -61.4(2) . . . . ? Cl4 C4 C5 C6 179.53(17) . . . . ? C4 C5 C6 C1 -1.0(3) . . . . ? C2 C1 C6 C5 -55.7(2) . . . . ? C7 C1 C6 C5 63.6(2) . . . . ? Cl1 C1 C6 C5 -177.87(17) . . . . ? C2 C1 C7 C12 -71.3(2) . . . . ? C6 C1 C7 C12 171.81(17) . . . . ? Cl1 C1 C7 C12 54.2(2) . . . . ? C2 C1 C7 C8 53.4(2) . . . . ? C6 C1 C7 C8 -63.5(2) . . . . ? Cl1 C1 C7 C8 178.89(14) . . . . ? C3 C4 C8 C9 69.0(2) . . . . ? C5 C4 C8 C9 -174.38(18) . . . . ? Cl4 C4 C8 C9 -55.9(2) . . . . ? C3 C4 C8 C7 -55.7(2) . . . . ? C5 C4 C8 C7 60.9(2) . . . . ? Cl4 C4 C8 C7 179.41(14) . . . . ? C12 C7 C8 C4 130.82(17) . . . . ? C1 C7 C8 C4 1.5(2) . . . . ? C12 C7 C8 C9 1.4(2) . . . . ? C1 C7 C8 C9 -127.90(17) . . . . ? C4 C8 C9 C14 -68.5(2) . . . . ? C7 C8 C9 C14 56.0(2) . . . . ? C4 C8 C9 C10 173.11(18) . . . . ? C7 C8 C9 C10 -62.4(2) . . . . ? C14 C9 C10 C11 -57.5(3) . . . . ? C8 C9 C10 C11 61.3(3) . . . . ? C9 C10 C11 C12 0.8(3) . . . . ? C10 C11 C12 C13 56.1(3) . . . . ? C10 C11 C12 C7 -61.8(2) . . . . ? C1 C7 C12 C13 66.1(2) . . . . ? C8 C7 C12 C13 -57.9(2) . . . . ? C1 C7 C12 C11 -175.77(17) . . . . ? C8 C7 C12 C11 60.2(2) . . . . ? C14 O1 C13 C12 -101.1(2) . . . . ? C11 C12 C13 O1 8.3(3) . . . . ? C7 C12 C13 O1 124.58(19) . . . . ? C11 C12 C13 C14 -57.8(2) . . . . ? C7 C12 C13 C14 58.5(2) . . . . ? C13 O1 C14 C9 101.3(2) . . . . ? C12 C13 C14 O1 108.48(19) . . . . ? O1 C13 C14 C9 -108.5(2) . . . . ? C12 C13 C14 C9 0.0(3) . . . . ? C10 C9 C14 O1 -7.5(3) . . . . ? C8 C9 C14 O1 -124.18(18) . . . . ? C10 C9 C14 C13 58.4(2) . . . . ? C8 C9 C14 C13 -58.3(2) . . . . ? _audit_block_code C14H14Cl4O_qn045_trauner _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C14 H14 Cl4 O' _chemical_formula_sum 'C14 H14 Cl4 O' _chemical_formula_weight 340.071 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 4 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.61535(7) _exptl_crystal_F_000 696 _database_code_depnum_ccdc_archive 'CCDC 948942' ####################################################################### # # 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_qn075 #?# MeasurementCode _vrf_PLAT094_qn075 ; PROBLEM: Ratio of Maximum / Minimum Residual Density .... 2.69 RESPONSE: Q1 with 0.68 electrons/mm3 is located 1.409 \%A from H6B and cannot be assigned reasonably ; _audit_update_record 02-Mar-12 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _exptl_crystal_description block #?# e.g.: needle, platelet; pr _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 #?# in millimeters _exptl_crystal_size_mid 0.12 #?# in millimeters _exptl_crystal_size_min 0.09 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_creation_date 02-Mar-12 #?# style: 18-Aug-1998 _diffrn_ambient_temperature 173(2) #?# in K _diffrn_source_type 'FR 591 generator' _diffrn_source_power 3.025 #?# in kW _diffrn_source_voltage 55.00 #?# in kV _diffrn_source_current 55.00 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'MONTEL, graded multilayered X-ray optics' _diffrn_radiation_collimation 0.20 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD; rotation images; thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_special_details ? _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_UB_11 0.1303297 _diffrn_orient_matrix_UB_12 -0.0584504 _diffrn_orient_matrix_UB_13 0.0080771 _diffrn_orient_matrix_UB_21 -0.0624230 _diffrn_orient_matrix_UB_22 -0.0486156 _diffrn_orient_matrix_UB_23 0.0717337 _diffrn_orient_matrix_UB_31 -0.0518848 _diffrn_orient_matrix_UB_32 -0.0844461 _diffrn_orient_matrix_UB_33 -0.0455756 loop_ _reflns_scale_group_code _reflns_scale_meas_F 1 1.0 _cell_length_a 6.5349(2) _cell_length_b 8.8020(4) _cell_length_c 11.7531(5) _cell_angle_alpha 89.290(2) _cell_angle_beta 85.351(3) _cell_angle_gamma 89.283(3) _cell_volume 673.72(5) _cell_measurement_temperature 173(2) #?# in K _cell_measurement_reflns_used 2913 _cell_measurement_theta_min 3.134 _cell_measurement_theta_max 27.485 _cell_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -5 0 -1 0.108000 5 0 1 0.098000 0 -3 -4 0.084000 1 12 16 0.029000 -1 12 -16 0.024000 0 -3 4 0.068000 _exptl_absorpt_coefficient_mu 0.865 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_reflns_number 5617 #xl _diffrn_reflns_av_R_equivalents 0.0208 #xl _diffrn_reflns_av_sigmaI/netI 0.0318 #xl _diffrn_reflns_limit_h_min -8 #xl _diffrn_reflns_limit_h_max 8 #xl _diffrn_reflns_limit_k_min -11 #xl _diffrn_reflns_limit_k_max 10 #xl _diffrn_reflns_limit_l_min -15 #xl _diffrn_reflns_limit_l_max 15 #xl _diffrn_reflns_theta_min 3.45 #xl _diffrn_reflns_theta_max 27.60 #xl _diffrn_measured_fraction_theta_max 0.992 #xl _diffrn_reflns_theta_full 27.60 #xl _diffrn_measured_fraction_theta_full 0.992 #xl _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _reflns_number_total 3112 #xl _reflns_number_gt 2682 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0296P)^2^+0.6114P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details ? #xl _refine_ls_abs_structure_Flack ? #xl _refine_ls_number_reflns 3112 #xl _refine_ls_number_parameters 172 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0404 #xl _refine_ls_R_factor_gt 0.0326 #xl _refine_ls_wR_factor_ref 0.0820 #xl _refine_ls_wR_factor_gt 0.0775 #xl _refine_ls_goodness_of_fit_ref 1.041 #xl _refine_ls_restrained_S_all 1.041 #xl _refine_ls_shift/su_max 0.001 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.681 #xl _refine_diff_density_min -0.253 #xl _refine_diff_density_rms 0.065 #xl _refine_special_details ? _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement ; Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. ; _computing_molecular_graphics ? _computing_publication_material ? 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 Cl1 Cl 0.78180(8) 0.36418(6) 0.48694(4) 0.03120(13) Uani 1 1 d . . . Cl2 Cl 1.04715(7) 0.51121(5) 0.25027(4) 0.02744(13) Uani 1 1 d . . . Cl3 Cl 1.10835(7) 0.29199(6) 0.04725(4) 0.02686(13) Uani 1 1 d . . . Cl4 Cl 0.65957(7) 0.23386(6) -0.01593(4) 0.02648(12) Uani 1 1 d . . . O1 O 1.1484(2) -0.01873(18) 0.33083(13) 0.0317(3) Uani 1 1 d . . . C1 C 0.7443(3) 0.3212(2) 0.34090(15) 0.0213(4) Uani 1 1 d . . . C2 C 0.9532(3) 0.3223(2) 0.27044(15) 0.0198(4) Uani 1 1 d . . . H2 H 1.0534 0.2630 0.3139 0.024 Uiso 1 1 calc R . . C3 C 0.9231(3) 0.2351(2) 0.15795(15) 0.0190(4) Uani 1 1 d . . . C4 C 0.6951(3) 0.2626(2) 0.13242(15) 0.0194(4) Uani 1 1 d . . . C5 C 0.6094(3) 0.4200(2) 0.16364(17) 0.0226(4) Uani 1 1 d . . . H5A H 0.4706 0.4327 0.1366 0.027 Uiso 1 1 calc R . . H5B H 0.6990 0.4990 0.1263 0.027 Uiso 1 1 calc R . . C6 C 0.5985(3) 0.4380(2) 0.29370(17) 0.0248(4) Uani 1 1 d . . . H6A H 0.6393 0.5419 0.3131 0.030 Uiso 1 1 calc R . . H6B H 0.4566 0.4210 0.3272 0.030 Uiso 1 1 calc R . . C7 C 0.6491(3) 0.1629(2) 0.33436(15) 0.0192(4) Uani 1 1 d . . . H7 H 0.5167 0.1631 0.3834 0.023 Uiso 1 1 calc R . . C8 C 0.5984(3) 0.1338(2) 0.20693(15) 0.0186(4) Uani 1 1 d . . . H8 H 0.4480 0.1232 0.1991 0.022 Uiso 1 1 calc R . . C9 C 0.7232(3) -0.0052(2) 0.16482(16) 0.0220(4) Uani 1 1 d . . . H9 H 0.7042 -0.0231 0.0825 0.026 Uiso 1 1 calc R . . C10 C 0.9420(3) 0.0567(2) 0.17808(16) 0.0215(4) Uani 1 1 d . . . H10 H 1.0475 0.0091 0.1228 0.026 Uiso 1 1 calc R . . C11 C 0.9830(3) 0.0219(2) 0.30080(16) 0.0222(4) Uani 1 1 d . . . C12 C 0.7863(3) 0.0344(2) 0.37770(16) 0.0226(4) Uani 1 1 d . . . H12 H 0.8153 0.0504 0.4589 0.027 Uiso 1 1 calc R . . C13 C 0.6775(3) -0.1181(2) 0.36348(17) 0.0277(4) Uani 1 1 d . . . H13A H 0.7515 -0.2011 0.4010 0.033 Uiso 1 1 calc R . . H13B H 0.5353 -0.1128 0.3993 0.033 Uiso 1 1 calc R . . C14 C 0.6755(3) -0.1491(2) 0.23502(17) 0.0281(4) Uani 1 1 d . . . H14A H 0.7788 -0.2288 0.2127 0.034 Uiso 1 1 calc R . . H14B H 0.5389 -0.1869 0.2189 0.034 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 Cl1 0.0395(3) 0.0353(3) 0.0192(2) -0.0082(2) -0.00280(19) -0.0041(2) Cl2 0.0248(2) 0.0235(2) 0.0343(3) -0.00056(19) -0.00329(19) -0.00665(18) Cl3 0.0225(2) 0.0348(3) 0.0222(2) 0.00337(19) 0.00468(17) -0.00280(19) Cl4 0.0292(2) 0.0337(3) 0.0171(2) 0.00248(19) -0.00631(17) -0.00056(19) O1 0.0256(7) 0.0383(9) 0.0317(8) 0.0084(7) -0.0072(6) 0.0050(6) C1 0.0232(9) 0.0246(10) 0.0160(8) -0.0041(7) -0.0010(7) -0.0027(7) C2 0.0194(8) 0.0189(9) 0.0216(9) -0.0007(7) -0.0036(7) -0.0026(7) C3 0.0165(8) 0.0230(9) 0.0171(8) 0.0008(7) 0.0006(6) -0.0009(7) C4 0.0194(8) 0.0241(9) 0.0150(8) 0.0006(7) -0.0034(6) -0.0012(7) C5 0.0198(9) 0.0202(9) 0.0279(10) 0.0033(8) -0.0043(7) 0.0026(7) C6 0.0247(9) 0.0217(9) 0.0277(10) -0.0034(8) -0.0002(8) 0.0028(7) C7 0.0189(8) 0.0233(9) 0.0153(8) 0.0000(7) 0.0000(6) -0.0011(7) C8 0.0178(8) 0.0202(9) 0.0183(8) 0.0000(7) -0.0037(6) -0.0023(7) C9 0.0262(9) 0.0211(9) 0.0189(9) -0.0015(7) -0.0026(7) -0.0018(7) C10 0.0223(9) 0.0242(9) 0.0178(9) -0.0004(7) -0.0003(7) 0.0029(7) C11 0.0250(9) 0.0182(9) 0.0237(9) 0.0025(7) -0.0048(7) -0.0005(7) C12 0.0258(9) 0.0254(10) 0.0170(9) 0.0020(7) -0.0032(7) -0.0011(8) C13 0.0330(10) 0.0238(10) 0.0259(10) 0.0070(8) -0.0016(8) -0.0040(8) C14 0.0383(11) 0.0201(10) 0.0263(10) 0.0006(8) -0.0049(8) -0.0043(8) 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 Cl1 C1 1.7988(18) . ? Cl2 C2 1.7864(18) . ? Cl3 C3 1.7755(18) . ? Cl4 C4 1.7989(18) . ? O1 C11 1.213(2) . ? C1 C6 1.523(3) . ? C1 C2 1.538(3) . ? C1 C7 1.539(3) . ? C2 C3 1.564(2) . ? C2 H2 1.0000 . ? C3 C4 1.559(2) . ? C3 C10 1.590(3) . ? C4 C5 1.525(3) . ? C4 C8 1.535(2) . ? C5 C6 1.534(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C12 1.542(3) . ? C7 C8 1.584(2) . ? C7 H7 1.0000 . ? C8 C9 1.526(3) . ? C8 H8 1.0000 . ? C9 C14 1.525(3) . ? C9 C10 1.557(3) . ? C9 H9 1.0000 . ? C10 C11 1.515(3) . ? C10 H10 1.0000 . ? C11 C12 1.514(3) . ? C12 C13 1.544(3) . ? C12 H12 1.0000 . ? C13 C14 1.539(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? 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 C6 C1 C2 110.54(15) . . ? C6 C1 C7 108.55(15) . . ? C2 C1 C7 109.13(15) . . ? C6 C1 Cl1 109.67(13) . . ? C2 C1 Cl1 109.15(12) . . ? C7 C1 Cl1 109.79(12) . . ? C1 C2 C3 106.44(14) . . ? C1 C2 Cl2 111.21(13) . . ? C3 C2 Cl2 114.99(13) . . ? C1 C2 H2 108.0 . . ? C3 C2 H2 108.0 . . ? Cl2 C2 H2 108.0 . . ? C4 C3 C2 106.20(14) . . ? C4 C3 C10 104.74(14) . . ? C2 C3 C10 110.65(14) . . ? C4 C3 Cl3 115.13(12) . . ? C2 C3 Cl3 110.67(12) . . ? C10 C3 Cl3 109.26(12) . . ? C5 C4 C8 113.87(15) . . ? C5 C4 C3 114.81(15) . . ? C8 C4 C3 98.15(14) . . ? C5 C4 Cl4 107.43(12) . . ? C8 C4 Cl4 111.07(12) . . ? C3 C4 Cl4 111.41(12) . . ? C4 C5 C6 109.28(15) . . ? C4 C5 H5A 109.8 . . ? C6 C5 H5A 109.8 . . ? C4 C5 H5B 109.8 . . ? C6 C5 H5B 109.8 . . ? H5A C5 H5B 108.3 . . ? C1 C6 C5 107.86(15) . . ? C1 C6 H6A 110.1 . . ? C5 C6 H6A 110.1 . . ? C1 C6 H6B 110.1 . . ? C5 C6 H6B 110.1 . . ? H6A C6 H6B 108.4 . . ? C1 C7 C12 113.15(15) . . ? C1 C7 C8 108.91(14) . . ? C12 C7 C8 110.89(15) . . ? C1 C7 H7 107.9 . . ? C12 C7 H7 107.9 . . ? C8 C7 H7 107.9 . . ? C9 C8 C4 102.66(14) . . ? C9 C8 C7 107.46(14) . . ? C4 C8 C7 107.54(14) . . ? C9 C8 H8 112.8 . . ? C4 C8 H8 112.8 . . ? C7 C8 H8 112.8 . . ? C14 C9 C8 113.85(16) . . ? C14 C9 C10 113.24(16) . . ? C8 C9 C10 98.56(14) . . ? C14 C9 H9 110.2 . . ? C8 C9 H9 110.2 . . ? C10 C9 H9 110.2 . . ? C11 C10 C9 105.17(15) . . ? C11 C10 C3 110.41(15) . . ? C9 C10 C3 105.03(14) . . ? C11 C10 H10 111.9 . . ? C9 C10 H10 111.9 . . ? C3 C10 H10 111.9 . . ? O1 C11 C12 125.41(18) . . ? O1 C11 C10 124.07(18) . . ? C12 C11 C10 110.38(15) . . ? C11 C12 C7 109.94(15) . . ? C11 C12 C13 104.53(16) . . ? C7 C12 C13 108.19(15) . . ? C11 C12 H12 111.3 . . ? C7 C12 H12 111.3 . . ? C13 C12 H12 111.3 . . ? C14 C13 C12 108.22(15) . . ? C14 C13 H13A 110.1 . . ? C12 C13 H13A 110.1 . . ? C14 C13 H13B 110.1 . . ? C12 C13 H13B 110.1 . . ? H13A C13 H13B 108.4 . . ? C9 C14 C13 110.90(16) . . ? C9 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.0 . . ? 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 C6 C1 C2 C3 -77.19(18) . . . . ? C7 C1 C2 C3 42.12(19) . . . . ? Cl1 C1 C2 C3 162.11(12) . . . . ? C6 C1 C2 Cl2 48.76(18) . . . . ? C7 C1 C2 Cl2 168.07(12) . . . . ? Cl1 C1 C2 Cl2 -71.94(15) . . . . ? C1 C2 C3 C4 30.44(19) . . . . ? Cl2 C2 C3 C4 -93.18(15) . . . . ? C1 C2 C3 C10 -82.68(17) . . . . ? Cl2 C2 C3 C10 153.70(12) . . . . ? C1 C2 C3 Cl3 156.06(12) . . . . ? Cl2 C2 C3 Cl3 32.43(16) . . . . ? C2 C3 C4 C5 35.8(2) . . . . ? C10 C3 C4 C5 152.91(15) . . . . ? Cl3 C3 C4 C5 -87.08(17) . . . . ? C2 C3 C4 C8 -85.34(16) . . . . ? C10 C3 C4 C8 31.80(16) . . . . ? Cl3 C3 C4 C8 151.81(12) . . . . ? C2 C3 C4 Cl4 158.15(12) . . . . ? C10 C3 C4 Cl4 -84.70(15) . . . . ? Cl3 C3 C4 Cl4 35.31(17) . . . . ? C8 C4 C5 C6 45.9(2) . . . . ? C3 C4 C5 C6 -66.18(19) . . . . ? Cl4 C4 C5 C6 169.31(12) . . . . ? C2 C1 C6 C5 46.8(2) . . . . ? C7 C1 C6 C5 -72.88(18) . . . . ? Cl1 C1 C6 C5 167.18(13) . . . . ? C4 C5 C6 C1 20.3(2) . . . . ? C6 C1 C7 C12 178.74(15) . . . . ? C2 C1 C7 C12 58.20(19) . . . . ? Cl1 C1 C7 C12 -61.40(18) . . . . ? C6 C1 C7 C8 54.93(19) . . . . ? C2 C1 C7 C8 -65.61(18) . . . . ? Cl1 C1 C7 C8 174.79(12) . . . . ? C5 C4 C8 C9 -175.25(14) . . . . ? C3 C4 C8 C9 -53.45(16) . . . . ? Cl4 C4 C8 C9 63.31(15) . . . . ? C5 C4 C8 C7 -62.08(18) . . . . ? C3 C4 C8 C7 59.73(16) . . . . ? Cl4 C4 C8 C7 176.49(11) . . . . ? C1 C7 C8 C9 119.10(16) . . . . ? C12 C7 C8 C9 -6.04(19) . . . . ? C1 C7 C8 C4 9.20(19) . . . . ? C12 C7 C8 C4 -115.94(16) . . . . ? C4 C8 C9 C14 173.10(15) . . . . ? C7 C8 C9 C14 59.86(19) . . . . ? C4 C8 C9 C10 52.91(16) . . . . ? C7 C8 C9 C10 -60.32(16) . . . . ? C14 C9 C10 C11 -34.6(2) . . . . ? C8 C9 C10 C11 86.00(16) . . . . ? C14 C9 C10 C3 -151.18(15) . . . . ? C8 C9 C10 C3 -30.54(17) . . . . ? C4 C3 C10 C11 -113.84(16) . . . . ? C2 C3 C10 C11 0.2(2) . . . . ? Cl3 C3 C10 C11 122.30(14) . . . . ? C4 C3 C10 C9 -0.95(18) . . . . ? C2 C3 C10 C9 113.10(15) . . . . ? Cl3 C3 C10 C9 -124.80(13) . . . . ? C9 C10 C11 O1 141.83(19) . . . . ? C3 C10 C11 O1 -105.4(2) . . . . ? C9 C10 C11 C12 -34.2(2) . . . . ? C3 C10 C11 C12 78.65(18) . . . . ? O1 C11 C12 C7 149.04(19) . . . . ? C10 C11 C12 C7 -35.0(2) . . . . ? O1 C11 C12 C13 -95.0(2) . . . . ? C10 C11 C12 C13 80.87(18) . . . . ? C1 C7 C12 C11 -64.7(2) . . . . ? C8 C7 C12 C11 57.97(19) . . . . ? C1 C7 C12 C13 -178.34(15) . . . . ? C8 C7 C12 C13 -55.62(19) . . . . ? C11 C12 C13 C14 -49.0(2) . . . . ? C7 C12 C13 C14 68.1(2) . . . . ? C8 C9 C14 C13 -48.4(2) . . . . ? C10 C9 C14 C13 63.1(2) . . . . ? C12 C13 C14 C9 -15.9(2) . . . . ? _audit_block_code C14H14Cl4O_qn075_trauner _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C14 H14 Cl4 O' _chemical_formula_sum 'C14 H14 Cl4 O' _chemical_formula_weight 340.071 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 2 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.67639(12) _exptl_crystal_F_000 348 _database_code_depnum_ccdc_archive 'CCDC 948943' ####################################################################### # # 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_qn096 #?# MeasurementCode _vrf_PLAT434_qn096 ; PROBLEM: Short Inter HL..HL Contact Br2 .. Br2 . 3.28 Ang. RESPONSE: space group and atom assignments are correct ; _audit_update_record 29-Mar-12 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _exptl_crystal_description block #?# e.g.: needle, platelet; _exptl_crystal_colour colourless _exptl_crystal_size_max 0.03 #?# in millimeters _exptl_crystal_size_mid 0.03 #?# in millimeters _exptl_crystal_size_min 0.02 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_creation_date 29-Mar-12 #?# style: 18-Aug-1998 _diffrn_ambient_temperature 173(2) #?# in K _diffrn_source_type 'FR 591 generator' _diffrn_source_power 3.025 #?# in kW _diffrn_source_voltage 55.00 #?# in kV _diffrn_source_current 55.00 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'MONTEL, graded multilayered X-ray optics' _diffrn_radiation_collimation 0.20 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD; rotation images; thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_special_details ? _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_UB_11 0.0569202 _diffrn_orient_matrix_UB_12 0.0742755 _diffrn_orient_matrix_UB_13 0.0061434 _diffrn_orient_matrix_UB_21 0.0381646 _diffrn_orient_matrix_UB_22 -0.1114805 _diffrn_orient_matrix_UB_23 -0.0026755 _diffrn_orient_matrix_UB_31 0.0023972 _diffrn_orient_matrix_UB_32 0.0111937 _diffrn_orient_matrix_UB_33 -0.0674108 loop_ _reflns_scale_group_code _reflns_scale_meas_F 1 1.0 _cell_length_a 14.7642(7) _cell_length_b 7.4391(3) _cell_length_c 14.5856(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.061(2) _cell_angle_gamma 90.00 _cell_volume 1601.70(12) _cell_measurement_temperature 173(2) #?# in K _cell_measurement_reflns_used 5620 _cell_measurement_theta_min 3.134 _cell_measurement_theta_max 25.350 _cell_special_details ? _exptl_absorpt_coefficient_mu 5.714 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_reflns_number 9823 #xl _diffrn_reflns_av_R_equivalents 0.0867 #xl _diffrn_reflns_av_sigmaI/netI 0.0662 #xl _diffrn_reflns_limit_h_min -17 #xl _diffrn_reflns_limit_h_max 16 #xl _diffrn_reflns_limit_k_min -8 #xl _diffrn_reflns_limit_k_max 8 #xl _diffrn_reflns_limit_l_min -17 #xl _diffrn_reflns_limit_l_max 17 #xl _diffrn_reflns_theta_min 3.14 #xl _diffrn_reflns_theta_max 25.35 #xl _diffrn_measured_fraction_theta_max 0.996 #xl _diffrn_reflns_theta_full 25.35 #xl _diffrn_measured_fraction_theta_full 0.996 #xl _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _reflns_number_total 2911 #xl _reflns_number_gt 2061 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.0737P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details ? #xl _refine_ls_abs_structure_Flack ? #xl _refine_ls_number_reflns 2911 #xl _refine_ls_number_parameters 181 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0647 #xl _refine_ls_R_factor_gt 0.0366 #xl _refine_ls_wR_factor_ref 0.0903 #xl _refine_ls_wR_factor_gt 0.0819 #xl _refine_ls_goodness_of_fit_ref 1.028 #xl _refine_ls_restrained_S_all 1.028 #xl _refine_ls_shift/su_max 0.000 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.827 #xl _refine_diff_density_min -0.722 #xl _refine_diff_density_rms 0.091 #xl _refine_special_details ? _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement ; Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. ; _computing_molecular_graphics ? _computing_publication_material ? 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 0.34767(3) 0.42996(6) 0.23131(3) 0.04127(16) Uani 1 1 d . . . Br2 Br 0.42094(4) 0.35256(7) 0.02192(4) 0.0618(2) Uani 1 1 d . . . Cl1 Cl 0.27127(9) -0.24427(16) -0.08992(8) 0.0478(3) Uani 1 1 d . . . Cl2 Cl 0.14365(8) 0.09514(16) -0.09834(8) 0.0478(3) Uani 1 1 d . . . Cl3 Cl 0.05224(8) 0.22059(15) 0.09054(9) 0.0467(3) Uani 1 1 d . . . Cl4 Cl 0.09022(8) -0.01209(17) 0.26499(8) 0.0468(3) Uani 1 1 d . . . C1 C 0.2924(3) 0.2276(5) 0.1646(3) 0.0276(9) Uani 1 1 d . . . H1 H 0.2266 0.2558 0.1559 0.033 Uiso 1 1 calc R . . C2 C 0.3303(3) 0.1855(5) 0.0687(3) 0.0306(10) Uani 1 1 d . . . H2 H 0.2778 0.1880 0.0245 0.037 Uiso 1 1 calc R . . C3 C 0.3681(3) -0.0054(5) 0.0677(3) 0.0293(9) Uani 1 1 d . . . H3 H 0.3946 -0.0308 0.0065 0.035 Uiso 1 1 calc R . . C4 C 0.4417(3) -0.0244(6) 0.1426(3) 0.0375(11) Uani 1 1 d . . . H4A H 0.4897 0.0665 0.1334 0.045 Uiso 1 1 calc R . . H4B H 0.4696 -0.1452 0.1394 0.045 Uiso 1 1 calc R . . C5 C 0.3984(3) 0.0029(6) 0.2373(3) 0.0329(10) Uani 1 1 d . . . H5A H 0.4019 -0.1105 0.2727 0.040 Uiso 1 1 calc R . . H5B H 0.4322 0.0964 0.2720 0.040 Uiso 1 1 calc R . . C6 C 0.2991(3) 0.0598(5) 0.2254(3) 0.0268(9) Uani 1 1 d . . . H6 H 0.2730 0.0861 0.2868 0.032 Uiso 1 1 calc R . . C7 C 0.2478(3) -0.0990(5) 0.1802(3) 0.0277(9) Uani 1 1 d . . . H7 H 0.2574 -0.2050 0.2214 0.033 Uiso 1 1 calc R . . C8 C 0.2945(3) -0.1455(5) 0.0881(3) 0.0263(9) Uani 1 1 d . . . H8 H 0.3263 -0.2630 0.0977 0.032 Uiso 1 1 calc R . . C9 C 0.2201(3) -0.1777(5) 0.0148(3) 0.0303(10) Uani 1 1 d . . . C10 C 0.1597(3) -0.0137(5) 0.0045(3) 0.0310(10) Uani 1 1 d . . . C11 C 0.1227(3) 0.0386(5) 0.0817(3) 0.0310(10) Uani 1 1 d . . . C12 C 0.1449(3) -0.0836(5) 0.1634(3) 0.0299(9) Uani 1 1 d . . . C13 C 0.1114(3) -0.2724(5) 0.1370(3) 0.0378(11) Uani 1 1 d . . . H13A H 0.0451 -0.2705 0.1256 0.045 Uiso 1 1 calc R . . H13B H 0.1246 -0.3577 0.1876 0.045 Uiso 1 1 calc R . . C14 C 0.1602(3) -0.3327(5) 0.0496(3) 0.0389(11) Uani 1 1 d . . . H14A H 0.1150 -0.3662 0.0016 0.047 Uiso 1 1 calc R . . H14B H 0.1982 -0.4393 0.0633 0.047 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 Br1 0.0481(3) 0.0283(2) 0.0472(3) -0.0084(2) -0.0068(2) -0.0019(2) Br2 0.0694(4) 0.0463(3) 0.0709(4) -0.0038(3) 0.0345(3) -0.0272(3) Cl1 0.0631(8) 0.0524(7) 0.0280(7) -0.0104(5) 0.0009(5) 0.0017(6) Cl2 0.0463(7) 0.0556(7) 0.0412(7) 0.0213(6) -0.0094(5) -0.0038(6) Cl3 0.0306(6) 0.0352(6) 0.0741(9) 0.0050(6) -0.0032(6) 0.0066(5) Cl4 0.0374(7) 0.0580(7) 0.0457(8) 0.0024(6) 0.0182(5) 0.0038(5) C1 0.021(2) 0.028(2) 0.034(3) -0.0009(19) -0.0012(17) -0.0025(17) C2 0.028(2) 0.030(2) 0.034(3) 0.0049(19) 0.0055(18) -0.0073(17) C3 0.029(2) 0.036(2) 0.023(2) -0.0043(19) 0.0063(17) -0.0012(18) C4 0.030(3) 0.043(3) 0.039(3) -0.009(2) 0.000(2) 0.002(2) C5 0.036(3) 0.033(2) 0.030(3) -0.002(2) -0.0049(18) 0.0070(19) C6 0.035(3) 0.025(2) 0.020(2) -0.0025(17) 0.0015(17) -0.0021(17) C7 0.028(2) 0.029(2) 0.026(2) 0.0018(18) 0.0012(17) -0.0005(17) C8 0.031(2) 0.022(2) 0.026(2) 0.0021(17) 0.0014(17) 0.0017(17) C9 0.037(3) 0.031(2) 0.023(2) 0.0014(18) 0.0012(17) -0.0046(18) C10 0.032(3) 0.028(2) 0.033(3) 0.008(2) -0.0066(19) -0.0066(18) C11 0.024(2) 0.024(2) 0.045(3) 0.0050(19) -0.0027(19) -0.0035(17) C12 0.030(2) 0.032(2) 0.028(2) 0.0040(19) 0.0079(17) -0.0022(18) C13 0.034(3) 0.031(2) 0.049(3) 0.006(2) -0.001(2) -0.0063(19) C14 0.043(3) 0.028(2) 0.045(3) 0.003(2) -0.011(2) -0.0081(19) 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 C1 1.962(4) . ? Br2 C2 1.959(4) . ? Cl1 C9 1.787(4) . ? Cl2 C10 1.717(4) . ? Cl3 C11 1.713(4) . ? Cl4 C12 1.781(4) . ? C1 C6 1.534(5) . ? C1 C2 1.547(6) . ? C1 H1 1.0000 . ? C2 C3 1.526(5) . ? C2 H2 1.0000 . ? C3 C4 1.533(6) . ? C3 C8 1.539(5) . ? C3 H3 1.0000 . ? C4 C5 1.546(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.532(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.545(5) . ? C6 H6 1.0000 . ? C7 C12 1.539(6) . ? C7 C8 1.560(5) . ? C7 H7 1.0000 . ? C8 C9 1.537(6) . ? C8 H8 1.0000 . ? C9 C10 1.517(6) . ? C9 C14 1.544(5) . ? C10 C11 1.320(6) . ? C11 C12 1.530(6) . ? C12 C13 1.536(5) . ? C13 C14 1.542(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? 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 C6 C1 C2 109.8(3) . . ? C6 C1 Br1 108.4(3) . . ? C2 C1 Br1 116.7(3) . . ? C6 C1 H1 107.2 . . ? C2 C1 H1 107.2 . . ? Br1 C1 H1 107.2 . . ? C3 C2 C1 109.6(3) . . ? C3 C2 Br2 109.6(3) . . ? C1 C2 Br2 116.6(3) . . ? C3 C2 H2 106.9 . . ? C1 C2 H2 106.9 . . ? Br2 C2 H2 106.9 . . ? C2 C3 C4 109.5(3) . . ? C2 C3 C8 111.7(3) . . ? C4 C3 C8 107.1(3) . . ? C2 C3 H3 109.5 . . ? C4 C3 H3 109.5 . . ? C8 C3 H3 109.5 . . ? C3 C4 C5 109.0(3) . . ? C3 C4 H4A 109.9 . . ? C5 C4 H4A 109.9 . . ? C3 C4 H4B 109.9 . . ? C5 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? C6 C5 C4 110.3(3) . . ? C6 C5 H5A 109.6 . . ? C4 C5 H5A 109.6 . . ? C6 C5 H5B 109.6 . . ? C4 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? C5 C6 C1 110.0(3) . . ? C5 C6 C7 107.3(3) . . ? C1 C6 C7 110.4(3) . . ? C5 C6 H6 109.7 . . ? C1 C6 H6 109.7 . . ? C7 C6 H6 109.7 . . ? C12 C7 C6 119.1(3) . . ? C12 C7 C8 109.3(3) . . ? C6 C7 C8 108.4(3) . . ? C12 C7 H7 106.4 . . ? C6 C7 H7 106.4 . . ? C8 C7 H7 106.4 . . ? C9 C8 C3 118.0(3) . . ? C9 C8 C7 108.2(3) . . ? C3 C8 C7 110.0(3) . . ? C9 C8 H8 106.7 . . ? C3 C8 H8 106.7 . . ? C7 C8 H8 106.7 . . ? C10 C9 C8 110.8(3) . . ? C10 C9 C14 107.1(3) . . ? C8 C9 C14 107.1(3) . . ? C10 C9 Cl1 113.2(3) . . ? C8 C9 Cl1 109.3(3) . . ? C14 C9 Cl1 109.1(3) . . ? C11 C10 C9 113.8(4) . . ? C11 C10 Cl2 123.6(3) . . ? C9 C10 Cl2 122.5(3) . . ? C10 C11 C12 113.8(3) . . ? C10 C11 Cl3 124.0(3) . . ? C12 C11 Cl3 122.2(3) . . ? C11 C12 C13 106.5(3) . . ? C11 C12 C7 111.4(3) . . ? C13 C12 C7 106.5(3) . . ? C11 C12 Cl4 112.1(3) . . ? C13 C12 Cl4 109.5(3) . . ? C7 C12 Cl4 110.6(3) . . ? C12 C13 C14 108.7(3) . . ? C12 C13 H13A 109.9 . . ? C14 C13 H13A 109.9 . . ? C12 C13 H13B 109.9 . . ? C14 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C13 C14 C9 109.5(3) . . ? C13 C14 H14A 109.8 . . ? C9 C14 H14A 109.8 . . ? C13 C14 H14B 109.8 . . ? C9 C14 H14B 109.8 . . ? H14A C14 H14B 108.2 . . ? 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 C6 C1 C2 C3 -3.9(4) . . . . ? Br1 C1 C2 C3 119.9(3) . . . . ? C6 C1 C2 Br2 -129.0(3) . . . . ? Br1 C1 C2 Br2 -5.2(4) . . . . ? C1 C2 C3 C4 -57.8(4) . . . . ? Br2 C2 C3 C4 71.3(4) . . . . ? C1 C2 C3 C8 60.6(4) . . . . ? Br2 C2 C3 C8 -170.3(3) . . . . ? C2 C3 C4 C5 63.6(4) . . . . ? C8 C3 C4 C5 -57.6(4) . . . . ? C3 C4 C5 C6 -6.1(5) . . . . ? C4 C5 C6 C1 -55.0(4) . . . . ? C4 C5 C6 C7 65.1(4) . . . . ? C2 C1 C6 C5 60.9(4) . . . . ? Br1 C1 C6 C5 -67.6(4) . . . . ? C2 C1 C6 C7 -57.3(4) . . . . ? Br1 C1 C6 C7 174.1(3) . . . . ? C5 C6 C7 C12 177.4(3) . . . . ? C1 C6 C7 C12 -62.7(4) . . . . ? C5 C6 C7 C8 -56.8(4) . . . . ? C1 C6 C7 C8 63.0(4) . . . . ? C2 C3 C8 C9 70.2(4) . . . . ? C4 C3 C8 C9 -170.0(3) . . . . ? C2 C3 C8 C7 -54.4(4) . . . . ? C4 C3 C8 C7 65.4(4) . . . . ? C12 C7 C8 C9 -5.4(4) . . . . ? C6 C7 C8 C9 -136.7(3) . . . . ? C12 C7 C8 C3 124.7(3) . . . . ? C6 C7 C8 C3 -6.6(4) . . . . ? C3 C8 C9 C10 -67.6(4) . . . . ? C7 C8 C9 C10 57.9(4) . . . . ? C3 C8 C9 C14 175.9(3) . . . . ? C7 C8 C9 C14 -58.6(4) . . . . ? C3 C8 C9 Cl1 57.9(4) . . . . ? C7 C8 C9 Cl1 -176.6(2) . . . . ? C8 C9 C10 C11 -55.8(5) . . . . ? C14 C9 C10 C11 60.7(4) . . . . ? Cl1 C9 C10 C11 -178.9(3) . . . . ? C8 C9 C10 Cl2 122.9(3) . . . . ? C14 C9 C10 Cl2 -120.6(3) . . . . ? Cl1 C9 C10 Cl2 -0.3(4) . . . . ? C9 C10 C11 C12 -3.0(5) . . . . ? Cl2 C10 C11 C12 178.3(3) . . . . ? C9 C10 C11 Cl3 179.5(3) . . . . ? Cl2 C10 C11 Cl3 0.8(5) . . . . ? C10 C11 C12 C13 -58.2(4) . . . . ? Cl3 C11 C12 C13 119.3(3) . . . . ? C10 C11 C12 C7 57.5(5) . . . . ? Cl3 C11 C12 C7 -124.9(3) . . . . ? C10 C11 C12 Cl4 -177.9(3) . . . . ? Cl3 C11 C12 Cl4 -0.4(4) . . . . ? C6 C7 C12 C11 75.6(4) . . . . ? C8 C7 C12 C11 -49.7(4) . . . . ? C6 C7 C12 C13 -168.6(4) . . . . ? C8 C7 C12 C13 66.0(4) . . . . ? C6 C7 C12 Cl4 -49.8(4) . . . . ? C8 C7 C12 Cl4 -175.1(3) . . . . ? C11 C12 C13 C14 59.2(4) . . . . ? C7 C12 C13 C14 -59.9(4) . . . . ? Cl4 C12 C13 C14 -179.4(3) . . . . ? C12 C13 C14 C9 -4.2(5) . . . . ? C10 C9 C14 C13 -53.8(4) . . . . ? C8 C9 C14 C13 65.1(4) . . . . ? Cl1 C9 C14 C13 -176.7(3) . . . . ? _audit_block_code C14H14Br2Cl4_qn096_trauner _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C14 H14 Br2 Cl4' _chemical_formula_sum 'C14 H14 Br2 Cl4' _chemical_formula_weight 483.880 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 4 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 2.00665(15) _exptl_crystal_F_000 944 _database_code_depnum_ccdc_archive 'CCDC 948944' ####################################################################### # # 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_qo048 #?# MeasurementCode _audit_update_record 27-Mar-12 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _exptl_crystal_description block #?# e.g.: needle, platelet; prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 #?# in millimeters _exptl_crystal_size_mid 0.10 #?# in millimeters _exptl_crystal_size_min 0.06 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_creation_date ; 'Tue Mar 27 13:32:41 2012' ; _diffrn_ambient_temperature 173(2) #?# in K _diffrn_source_type 'Spellman generator' _diffrn_source_power 2.00_kW #?# in kW _diffrn_source_voltage 50_kV #?# in kV _diffrn_source_current 40_mA #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation '0.5 mm collimator' _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Oxford XCalibur' _diffrn_measurement_method '\w scans' _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -9.00 94.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 21.2306 77.0000 120.0000 103 #__ type_ start__ end____ width___ exp.time_ 2 omega -12.00 93.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 21.2306 77.0000 -120.0000 105 #__ type_ start__ end____ width___ exp.time_ 3 omega -9.00 93.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 21.2306 71.0000 12.0000 102 ; _diffrn_detector_area_resol_mean 15.9809 _diffrn_special_details ? _diffrn_orient_matrix_type ? _diffrn_orient_matrix_UB_11 0.0195740000 _diffrn_orient_matrix_UB_12 0.0476312000 _diffrn_orient_matrix_UB_13 -0.0235102000 _diffrn_orient_matrix_UB_21 0.0344955000 _diffrn_orient_matrix_UB_22 -0.0333910000 _diffrn_orient_matrix_UB_23 -0.0310018000 _diffrn_orient_matrix_UB_31 -0.0743563000 _diffrn_orient_matrix_UB_32 -0.0029189000 _diffrn_orient_matrix_UB_33 -0.0289973000 loop_ _reflns_scale_group_code _reflns_scale_meas_F ? ? _cell_length_a 8.5158(3) _cell_length_b 12.1809(5) _cell_length_c 14.7928(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.852(3) _cell_angle_gamma 90.00 _cell_volume 1516.18(10) _cell_measurement_temperature 173(2) #?# in K _cell_measurement_reflns_used 3533 _cell_measurement_theta_min 4.1743 _cell_measurement_theta_max 26.3078 _cell_special_details ? _exptl_absorpt_coefficient_mu 6.037 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.54047 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_reflns_number 8102 #xl _diffrn_reflns_av_R_equivalents 0.0410 #xl _diffrn_reflns_av_sigmaI/netI 0.0415 #xl _diffrn_reflns_limit_h_min -6 #xl _diffrn_reflns_limit_h_max 10 #xl _diffrn_reflns_limit_k_min -14 #xl _diffrn_reflns_limit_k_max 15 #xl _diffrn_reflns_limit_l_min -17 #xl _diffrn_reflns_limit_l_max 18 #xl _diffrn_reflns_theta_min 4.24 #xl _diffrn_reflns_theta_max 26.36 #xl _diffrn_measured_fraction_theta_max 0.995 #xl _diffrn_reflns_theta_full 26.36 #xl _diffrn_measured_fraction_theta_full 0.995 #xl _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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' 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' 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' _reflns_number_total 3084 #xl _reflns_number_gt 2662 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0771P)^2^+0.4065P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details ? #xl _refine_ls_abs_structure_Flack ? #xl _refine_ls_number_reflns 3084 #xl _refine_ls_number_parameters 182 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0487 #xl _refine_ls_R_factor_gt 0.0424 #xl _refine_ls_wR_factor_ref 0.1162 #xl _refine_ls_wR_factor_gt 0.1100 #xl _refine_ls_goodness_of_fit_ref 1.025 #xl _refine_ls_restrained_S_all 1.025 #xl _refine_ls_shift/su_max 0.001 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 1.090 #xl _refine_diff_density_min -1.433 #xl _refine_diff_density_rms 0.149 #xl _refine_special_details ; Br1 and Cl1 bound to C1 are disordered (site of Cl1 is occupied by Br11, site of Br1 is occupied by Cl11), sof ratio 0.70/0.30 ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement ; Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. ; _computing_molecular_graphics ? _computing_publication_material ? 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 0.37223(5) 0.23366(4) 0.23601(3) 0.02003(18) Uani 0.697(2) 1 d P . . Cl11 Cl 0.37223(5) 0.23366(4) 0.23601(3) 0.02003(18) Uani 0.303(2) 1 d P . . Br2 Br 1.03635(5) 0.23091(4) 0.35826(3) 0.02716(16) Uani 1 1 d . . . Cl1 Cl 0.32439(8) 0.11965(5) 0.05932(4) 0.0224(2) Uani 0.697(2) 1 d P . . Br11 Br 0.32439(8) 0.11965(5) 0.05932(4) 0.0224(2) Uani 0.303(2) 1 d P . . Cl2 Cl 0.34471(11) 0.41679(8) 0.07585(7) 0.0237(2) Uani 1 1 d . . . Cl3 Cl 0.87908(10) 0.08253(8) 0.05578(6) 0.0211(2) Uani 1 1 d . . . Cl4 Cl 0.63493(11) 0.02570(7) 0.18667(6) 0.0200(2) Uani 1 1 d . . . C1 C 0.4704(4) 0.2129(3) 0.1276(2) 0.0147(7) Uani 1 1 d . . . C2 C 0.5003(4) 0.3186(3) 0.0731(2) 0.0164(7) Uani 1 1 d . . . C3 C 0.5074(5) 0.2874(3) -0.0256(2) 0.0197(8) Uani 1 1 d . . . H3A H 0.5469 0.3500 -0.0583 0.024 Uiso 1 1 calc R . . H3B H 0.4002 0.2674 -0.0571 0.024 Uiso 1 1 calc R . . C4 C 0.6215(4) 0.1884(3) -0.0248(2) 0.0185(8) Uani 1 1 d . . . H4A H 0.5596 0.1195 -0.0345 0.022 Uiso 1 1 calc R . . H4B H 0.6859 0.1960 -0.0747 0.022 Uiso 1 1 calc R . . C5 C 0.7298(4) 0.1847(3) 0.0672(2) 0.0145(7) Uani 1 1 d . . . C6 C 0.6418(4) 0.1654(3) 0.1538(2) 0.0132(7) Uani 1 1 d . . . C7 C 0.7303(4) 0.2338(3) 0.2369(2) 0.0138(7) Uani 1 1 d . . . H7 H 0.6998 0.2085 0.2961 0.017 Uiso 1 1 calc R . . C8 C 0.9078(4) 0.2169(3) 0.2353(2) 0.0163(7) Uani 1 1 d . . . H8 H 0.9228 0.1409 0.2127 0.020 Uiso 1 1 calc R . . C9 C 0.9503(4) 0.2978(3) 0.1634(3) 0.0182(7) Uani 1 1 d . . . H9 H 1.0486 0.2739 0.1395 0.022 Uiso 1 1 calc R . . C10 C 0.9705(5) 0.4137(3) 0.2044(3) 0.0253(9) Uani 1 1 d . . . H10A H 1.0725 0.4191 0.2465 0.030 Uiso 1 1 calc R . . H10B H 0.9709 0.4687 0.1551 0.030 Uiso 1 1 calc R . . C11 C 0.8309(5) 0.4350(3) 0.2564(3) 0.0247(9) Uani 1 1 d . . . H11A H 0.8648 0.4216 0.3225 0.030 Uiso 1 1 calc R . . H11B H 0.7966 0.5125 0.2483 0.030 Uiso 1 1 calc R . . C12 C 0.6921(4) 0.3589(3) 0.2201(2) 0.0165(7) Uani 1 1 d . . . H12 H 0.5943 0.3799 0.2457 0.020 Uiso 1 1 calc R . . C13 C 0.6636(4) 0.3670(3) 0.1158(2) 0.0174(7) Uani 1 1 d . . . H13 H 0.6712 0.4454 0.0967 0.021 Uiso 1 1 calc R . . C14 C 0.8046(4) 0.2986(3) 0.0860(2) 0.0151(7) Uani 1 1 d . . . H14 H 0.8352 0.3298 0.0286 0.018 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 Br1 0.0152(3) 0.0275(3) 0.0181(3) 0.00004(17) 0.00463(19) 0.00151(17) Cl11 0.0152(3) 0.0275(3) 0.0181(3) 0.00004(17) 0.00463(19) 0.00151(17) Br2 0.0164(2) 0.0434(3) 0.0194(2) -0.00638(16) -0.00469(17) 0.00219(16) Cl1 0.0207(4) 0.0230(4) 0.0223(4) -0.0028(3) -0.0007(3) -0.0043(3) Br11 0.0207(4) 0.0230(4) 0.0223(4) -0.0028(3) -0.0007(3) -0.0043(3) Cl2 0.0213(5) 0.0214(5) 0.0280(5) 0.0041(4) 0.0021(4) 0.0088(4) Cl3 0.0172(4) 0.0233(5) 0.0228(5) -0.0072(4) 0.0034(4) 0.0052(4) Cl4 0.0199(4) 0.0132(4) 0.0264(5) 0.0052(3) 0.0014(4) -0.0008(3) C1 0.0132(17) 0.0204(18) 0.0104(15) -0.0018(13) 0.0019(13) 0.0010(13) C2 0.0140(17) 0.0149(17) 0.0206(18) 0.0030(14) 0.0030(14) 0.0044(14) C3 0.023(2) 0.0205(19) 0.0151(18) 0.0013(14) 0.0004(15) 0.0028(15) C4 0.0179(18) 0.0224(19) 0.0158(17) -0.0044(15) 0.0046(14) -0.0009(15) C5 0.0143(16) 0.0162(17) 0.0140(16) -0.0025(14) 0.0049(13) 0.0020(14) C6 0.0152(17) 0.0132(16) 0.0109(16) 0.0019(13) 0.0007(13) -0.0015(13) C7 0.0099(17) 0.0167(17) 0.0141(17) -0.0011(13) -0.0005(13) -0.0008(13) C8 0.0135(17) 0.0183(18) 0.0158(17) -0.0055(14) -0.0018(14) 0.0000(14) C9 0.0100(17) 0.0222(19) 0.0220(18) -0.0045(15) 0.0009(14) -0.0037(14) C10 0.023(2) 0.020(2) 0.032(2) -0.0057(17) 0.0031(17) -0.0110(16) C11 0.0202(19) 0.024(2) 0.028(2) -0.0092(16) -0.0016(16) -0.0011(16) C12 0.0144(17) 0.0182(18) 0.0161(17) -0.0040(14) -0.0006(14) 0.0000(14) C13 0.0175(18) 0.0138(17) 0.0209(18) 0.0024(14) 0.0034(14) -0.0002(14) C14 0.0123(17) 0.0166(17) 0.0172(17) 0.0022(14) 0.0051(13) -0.0011(14) 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 C1 1.935(3) . ? Br2 C8 1.980(4) . ? Cl1 C1 1.863(4) . ? Cl2 C2 1.790(4) . ? Cl3 C5 1.805(3) . ? Cl4 C6 1.773(3) . ? C1 C2 1.560(5) . ? C1 C6 1.562(5) . ? C2 C3 1.518(5) . ? C2 C13 1.553(5) . ? C3 C4 1.547(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.523(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C14 1.534(5) . ? C5 C6 1.598(4) . ? C6 C7 1.577(5) . ? C7 C8 1.529(5) . ? C7 C12 1.569(5) . ? C7 H7 1.0000 . ? C8 C9 1.534(5) . ? C8 H8 1.0000 . ? C9 C10 1.536(5) . ? C9 C14 1.554(5) . ? C9 H9 1.0000 . ? C10 C11 1.535(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.534(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.528(5) . ? C12 H12 1.0000 . ? C13 C14 1.580(5) . ? C13 H13 1.0000 . ? C14 H14 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 102.3(3) . . ? C2 C1 Cl1 111.8(2) . . ? C6 C1 Cl1 115.4(2) . . ? C2 C1 Br1 116.5(2) . . ? C6 C1 Br1 110.4(2) . . ? Cl1 C1 Br1 101.03(17) . . ? C3 C2 C13 108.7(3) . . ? C3 C2 C1 108.9(3) . . ? C13 C2 C1 108.1(3) . . ? C3 C2 Cl2 109.2(2) . . ? C13 C2 Cl2 110.9(2) . . ? C1 C2 Cl2 111.0(2) . . ? C2 C3 C4 107.8(3) . . ? C2 C3 H3A 110.1 . . ? C4 C3 H3A 110.1 . . ? C2 C3 H3B 110.1 . . ? C4 C3 H3B 110.1 . . ? H3A C3 H3B 108.5 . . ? C5 C4 C3 108.9(3) . . ? C5 C4 H4A 109.9 . . ? C3 C4 H4A 109.9 . . ? C5 C4 H4B 109.9 . . ? C3 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? C4 C5 C14 108.2(3) . . ? C4 C5 C6 115.2(3) . . ? C14 C5 C6 102.7(3) . . ? C4 C5 Cl3 106.0(2) . . ? C14 C5 Cl3 111.2(2) . . ? C6 C5 Cl3 113.5(2) . . ? C1 C6 C7 108.3(3) . . ? C1 C6 C5 106.4(3) . . ? C7 C6 C5 108.7(3) . . ? C1 C6 Cl4 110.8(2) . . ? C7 C6 Cl4 109.0(2) . . ? C5 C6 Cl4 113.6(2) . . ? C8 C7 C12 108.0(3) . . ? C8 C7 C6 105.8(3) . . ? C12 C7 C6 109.1(3) . . ? C8 C7 H7 111.2 . . ? C12 C7 H7 111.2 . . ? C6 C7 H7 111.2 . . ? C7 C8 C9 105.3(3) . . ? C7 C8 Br2 112.5(2) . . ? C9 C8 Br2 115.2(2) . . ? C7 C8 H8 107.9 . . ? C9 C8 H8 107.9 . . ? Br2 C8 H8 107.9 . . ? C8 C9 C10 109.9(3) . . ? C8 C9 C14 105.6(3) . . ? C10 C9 C14 108.3(3) . . ? C8 C9 H9 111.0 . . ? C10 C9 H9 111.0 . . ? C14 C9 H9 111.0 . . ? C11 C10 C9 107.8(3) . . ? C11 C10 H10A 110.1 . . ? C9 C10 H10A 110.1 . . ? C11 C10 H10B 110.1 . . ? C9 C10 H10B 110.1 . . ? H10A C10 H10B 108.5 . . ? C12 C11 C10 109.7(3) . . ? C12 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? C12 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C13 C12 C11 107.9(3) . . ? C13 C12 C7 102.7(3) . . ? C11 C12 C7 113.7(3) . . ? C13 C12 H12 110.7 . . ? C11 C12 H12 110.7 . . ? C7 C12 H12 110.7 . . ? C12 C13 C2 112.3(3) . . ? C12 C13 C14 103.8(3) . . ? C2 C13 C14 110.9(3) . . ? C12 C13 H13 109.9 . . ? C2 C13 H13 109.9 . . ? C14 C13 H13 109.9 . . ? C5 C14 C9 113.0(3) . . ? C5 C14 C13 102.5(3) . . ? C9 C14 C13 110.6(3) . . ? C5 C14 H14 110.2 . . ? C9 C14 H14 110.2 . . ? C13 C14 H14 110.2 . . ? 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 C6 C1 C2 C3 84.0(3) . . . . ? Cl1 C1 C2 C3 -40.1(3) . . . . ? Br1 C1 C2 C3 -155.5(2) . . . . ? C6 C1 C2 C13 -34.0(3) . . . . ? Cl1 C1 C2 C13 -158.0(2) . . . . ? Br1 C1 C2 C13 86.5(3) . . . . ? C6 C1 C2 Cl2 -155.8(2) . . . . ? Cl1 C1 C2 Cl2 80.2(3) . . . . ? Br1 C1 C2 Cl2 -35.3(3) . . . . ? C13 C2 C3 C4 68.8(4) . . . . ? C1 C2 C3 C4 -48.8(4) . . . . ? Cl2 C2 C3 C4 -170.2(3) . . . . ? C2 C3 C4 C5 -20.8(4) . . . . ? C3 C4 C5 C14 -51.3(4) . . . . ? C3 C4 C5 C6 63.0(4) . . . . ? C3 C4 C5 Cl3 -170.7(3) . . . . ? C2 C1 C6 C7 77.8(3) . . . . ? Cl1 C1 C6 C7 -160.6(2) . . . . ? Br1 C1 C6 C7 -46.9(3) . . . . ? C2 C1 C6 C5 -38.9(3) . . . . ? Cl1 C1 C6 C5 82.7(3) . . . . ? Br1 C1 C6 C5 -163.5(2) . . . . ? C2 C1 C6 Cl4 -162.7(2) . . . . ? Cl1 C1 C6 Cl4 -41.2(3) . . . . ? Br1 C1 C6 Cl4 72.6(3) . . . . ? C4 C5 C6 C1 -27.8(4) . . . . ? C14 C5 C6 C1 89.6(3) . . . . ? Cl3 C5 C6 C1 -150.3(2) . . . . ? C4 C5 C6 C7 -144.2(3) . . . . ? C14 C5 C6 C7 -26.8(3) . . . . ? Cl3 C5 C6 C7 93.3(3) . . . . ? C4 C5 C6 Cl4 94.3(3) . . . . ? C14 C5 C6 Cl4 -148.3(2) . . . . ? Cl3 C5 C6 Cl4 -28.1(3) . . . . ? C1 C6 C7 C8 -158.2(3) . . . . ? C5 C6 C7 C8 -43.0(3) . . . . ? Cl4 C6 C7 C8 81.2(3) . . . . ? C1 C6 C7 C12 -42.2(4) . . . . ? C5 C6 C7 C12 73.0(3) . . . . ? Cl4 C6 C7 C12 -162.8(2) . . . . ? C12 C7 C8 C9 -35.2(4) . . . . ? C6 C7 C8 C9 81.5(3) . . . . ? C12 C7 C8 Br2 91.0(3) . . . . ? C6 C7 C8 Br2 -152.3(2) . . . . ? C7 C8 C9 C10 79.3(3) . . . . ? Br2 C8 C9 C10 -45.2(4) . . . . ? C7 C8 C9 C14 -37.2(4) . . . . ? Br2 C8 C9 C14 -161.8(2) . . . . ? C8 C9 C10 C11 -45.6(4) . . . . ? C14 C9 C10 C11 69.3(4) . . . . ? C9 C10 C11 C12 -22.1(4) . . . . ? C10 C11 C12 C13 -49.3(4) . . . . ? C10 C11 C12 C7 64.0(4) . . . . ? C8 C7 C12 C13 85.6(3) . . . . ? C6 C7 C12 C13 -29.0(4) . . . . ? C8 C7 C12 C11 -30.7(4) . . . . ? C6 C7 C12 C11 -145.3(3) . . . . ? C11 C12 C13 C2 -164.8(3) . . . . ? C7 C12 C13 C2 74.8(3) . . . . ? C11 C12 C13 C14 75.3(3) . . . . ? C7 C12 C13 C14 -45.1(3) . . . . ? C3 C2 C13 C12 -157.4(3) . . . . ? C1 C2 C13 C12 -39.3(4) . . . . ? Cl2 C2 C13 C12 82.6(3) . . . . ? C3 C2 C13 C14 -41.8(4) . . . . ? C1 C2 C13 C14 76.3(3) . . . . ? Cl2 C2 C13 C14 -161.8(2) . . . . ? C4 C5 C14 C9 -164.4(3) . . . . ? C6 C5 C14 C9 73.3(3) . . . . ? Cl3 C5 C14 C9 -48.4(3) . . . . ? C4 C5 C14 C13 76.6(3) . . . . ? C6 C5 C14 C13 -45.7(3) . . . . ? Cl3 C5 C14 C13 -167.4(2) . . . . ? C8 C9 C14 C5 -38.4(4) . . . . ? C10 C9 C14 C5 -156.0(3) . . . . ? C8 C9 C14 C13 75.9(3) . . . . ? C10 C9 C14 C13 -41.8(4) . . . . ? C12 C13 C14 C5 94.2(3) . . . . ? C2 C13 C14 C5 -26.6(4) . . . . ? C12 C13 C14 C9 -26.5(4) . . . . ? C2 C13 C14 C9 -147.3(3) . . . . ? _audit_block_code C14H14Br2Cl4_qo048_trauner _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C14 H14 Br2 Cl4' _chemical_formula_sum 'C14 H14 Br2 Cl4' _chemical_formula_weight 483.880 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 4 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 2.11983(14) _exptl_crystal_F_000 944 _database_code_depnum_ccdc_archive 'CCDC 948945' ####################################################################### # # 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_qo120 #?# MeasurementCode _audit_update_record 20-Jul-12 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _exptl_crystal_description platelet #?# e.g.: needle, platelet; prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 #?# in millimeters _exptl_crystal_size_mid 0.19 #?# in millimeters _exptl_crystal_size_min 0.04 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_creation_date ; 'Tue Jul 17 10:26:40 2012' ; _diffrn_ambient_temperature 173(2) #?# in K _diffrn_source_type 'Spellman generator' _diffrn_source_power 2.00_kW #?# in kW _diffrn_source_voltage 50_kV #?# in kV _diffrn_source_current 40_mA #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation '0.5 mm collimator' _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Oxford XCalibur' _diffrn_measurement_method '\w scans' _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -93.00 11.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -20.2931 -77.0000 -30.0000 104 #__ type_ start__ end____ width___ exp.time_ 2 omega -52.00 53.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 21.2306 -38.0000 -180.0000 105 ; _diffrn_detector_area_resol_mean 15.9809 _diffrn_special_details ? # 'no? crystal decay in terms of mean intensity per image' #?# Source instability, crystal motion, degradation, formation of ice _diffrn_orient_matrix_type ? _diffrn_orient_matrix_UB_11 0.0275131000 _diffrn_orient_matrix_UB_12 -0.0543032000 _diffrn_orient_matrix_UB_13 0.0423444000 _diffrn_orient_matrix_UB_21 -0.0480216000 _diffrn_orient_matrix_UB_22 -0.0383463000 _diffrn_orient_matrix_UB_23 0.0056095000 _diffrn_orient_matrix_UB_31 0.0055893000 _diffrn_orient_matrix_UB_32 -0.0629553000 _diffrn_orient_matrix_UB_33 -0.0397625000 loop_ _reflns_scale_group_code _reflns_scale_meas_F ? ? _cell_length_a 13.0330(10) _cell_length_b 7.7467(6) _cell_length_c 12.4282(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.998(7) _cell_angle_gamma 90.00 _cell_volume 1227.37(16) _cell_measurement_temperature 173(2) #?# in K _cell_measurement_reflns_used 1603 _cell_measurement_theta_min 4.2016 _cell_measurement_theta_max 28.7784 _cell_special_details ? _exptl_absorpt_coefficient_mu 6.574 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.41499 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_reflns_number 4608 #xl _diffrn_reflns_av_R_equivalents 0.0303 #xl _diffrn_reflns_av_sigmaI/netI 0.0516 #xl _diffrn_reflns_limit_h_min -11 #xl _diffrn_reflns_limit_h_max 16 #xl _diffrn_reflns_limit_k_min -10 #xl _diffrn_reflns_limit_k_max 5 #xl _diffrn_reflns_limit_l_min -15 #xl _diffrn_reflns_limit_l_max 17 #xl _diffrn_reflns_theta_min 4.21 #xl _diffrn_reflns_theta_max 28.84 #xl _diffrn_measured_fraction_theta_max 0.840 #xl _diffrn_reflns_theta_full 26.30 #xl _diffrn_measured_fraction_theta_full 0.992 #xl _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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' 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' _reflns_number_total 2708 #xl _reflns_number_gt 2166 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0453P)^2^+0.2889P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details ? #xl _refine_ls_abs_structure_Flack ? #xl _refine_ls_number_reflns 2708 #xl _refine_ls_number_parameters 145 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0553 #xl _refine_ls_R_factor_gt 0.0390 #xl _refine_ls_wR_factor_ref 0.1006 #xl _refine_ls_wR_factor_gt 0.0893 #xl _refine_ls_goodness_of_fit_ref 1.051 #xl _refine_ls_restrained_S_all 1.051 #xl _refine_ls_shift/su_max 0.000 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.878 #xl _refine_diff_density_min -0.977 #xl _refine_diff_density_rms 0.127 #xl _refine_special_details ? _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement ; Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. ; _computing_molecular_graphics ? _computing_publication_material ? 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 0.99088(3) 0.26333(6) 0.46974(3) 0.03272(15) Uani 1 1 d . . . Br2 Br 0.55503(3) -0.02159(5) 0.38354(3) 0.03321(15) Uani 1 1 d . . . C1 C 0.8998(3) 0.1320(5) 0.3501(3) 0.0225(8) Uani 1 1 d . . . H1 H 0.9315 0.0150 0.3471 0.027 Uiso 1 1 calc R . . C2 C 0.7865(3) 0.1069(5) 0.3645(3) 0.0209(8) Uani 1 1 d . . . H2 H 0.7823 0.1031 0.4439 0.025 Uiso 1 1 calc R . . C3 C 0.7518(3) -0.0690(5) 0.3051(3) 0.0220(8) Uani 1 1 d . . . H3 H 0.7779 -0.1696 0.3535 0.026 Uiso 1 1 calc R . . C4 C 0.6332(3) -0.0748(5) 0.2664(3) 0.0237(8) Uani 1 1 d . . . H4 H 0.6138 -0.1945 0.2397 0.028 Uiso 1 1 calc R . . C5 C 0.6080(3) 0.0473(5) 0.1664(3) 0.0227(8) Uani 1 1 d . . . H5 H 0.5355 0.0957 0.1566 0.027 Uiso 1 1 calc R . . C6 C 0.6197(3) -0.0677(5) 0.0678(3) 0.0300(9) Uani 1 1 d . . . H6A H 0.5597 -0.1483 0.0492 0.036 Uiso 1 1 calc R . . H6B H 0.6213 0.0047 0.0026 0.036 Uiso 1 1 calc R . . C7 C 0.7233(3) -0.1694(5) 0.1016(3) 0.0272(9) Uani 1 1 d . . . H7A H 0.7088 -0.2868 0.1262 0.033 Uiso 1 1 calc R . . H7B H 0.7576 -0.1804 0.0379 0.033 Uiso 1 1 calc R . . C8 C 0.7957(3) -0.0726(5) 0.1955(3) 0.0237(8) Uani 1 1 d . . . H8 H 0.8679 -0.1229 0.2096 0.028 Uiso 1 1 calc R . . C9 C 0.7982(3) 0.1183(5) 0.1626(3) 0.0211(8) Uani 1 1 d . . . H9 H 0.8027 0.1292 0.0835 0.025 Uiso 1 1 calc R . . C10 C 0.6911(3) 0.1914(5) 0.1815(3) 0.0224(8) Uani 1 1 d . . . H10 H 0.6669 0.2897 0.1303 0.027 Uiso 1 1 calc R . . C11 C 0.7171(3) 0.2543(4) 0.3019(3) 0.0213(8) Uani 1 1 d . . . H11 H 0.6515 0.2682 0.3308 0.026 Uiso 1 1 calc R . . C12 C 0.7757(3) 0.4267(5) 0.3064(3) 0.0302(9) Uani 1 1 d . . . H12A H 0.8057 0.4580 0.3837 0.036 Uiso 1 1 calc R . . H12B H 0.7267 0.5192 0.2735 0.036 Uiso 1 1 calc R . . C13 C 0.8643(3) 0.4075(5) 0.2415(3) 0.0301(9) Uani 1 1 d . . . H13A H 0.8409 0.4529 0.1659 0.036 Uiso 1 1 calc R . . H13B H 0.9270 0.4733 0.2782 0.036 Uiso 1 1 calc R . . C14 C 0.8909(3) 0.2158(5) 0.2377(3) 0.0231(8) Uani 1 1 d . . . H14 H 0.9572 0.1994 0.2104 0.028 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 Br1 0.0235(3) 0.0424(3) 0.0308(2) -0.00705(17) 0.00223(17) -0.00953(19) Br2 0.0262(3) 0.0402(3) 0.0373(2) -0.00044(18) 0.0159(2) -0.00765(19) C1 0.016(2) 0.0256(19) 0.0254(18) -0.0032(15) 0.0025(15) -0.0022(16) C2 0.019(2) 0.0250(18) 0.0192(16) 0.0007(14) 0.0048(15) -0.0018(16) C3 0.019(2) 0.0230(18) 0.0235(17) 0.0040(14) 0.0032(15) 0.0033(16) C4 0.019(2) 0.0255(19) 0.0275(18) -0.0027(15) 0.0058(16) 0.0003(17) C5 0.012(2) 0.0293(19) 0.0248(18) 0.0005(15) -0.0001(15) 0.0044(17) C6 0.027(3) 0.035(2) 0.0252(19) -0.0039(16) -0.0011(17) 0.0026(19) C7 0.023(2) 0.033(2) 0.0244(18) -0.0060(16) 0.0010(16) 0.0013(19) C8 0.019(2) 0.030(2) 0.0222(17) -0.0024(15) 0.0045(15) 0.0052(17) C9 0.014(2) 0.030(2) 0.0191(16) 0.0038(14) 0.0031(14) 0.0027(16) C10 0.018(2) 0.0243(18) 0.0240(18) 0.0029(15) 0.0024(15) 0.0045(17) C11 0.016(2) 0.0226(18) 0.0265(18) -0.0015(14) 0.0078(16) 0.0011(16) C12 0.029(3) 0.0229(19) 0.041(2) 0.0014(16) 0.012(2) 0.0013(18) C13 0.029(3) 0.026(2) 0.037(2) 0.0041(17) 0.0113(19) -0.0052(19) C14 0.014(2) 0.029(2) 0.0274(19) 0.0011(15) 0.0088(16) -0.0014(17) 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 C1 1.980(4) . ? Br2 C4 1.985(3) . ? C1 C14 1.523(5) . ? C1 C2 1.536(5) . ? C1 H1 1.0000 . ? C2 C11 1.560(5) . ? C2 C3 1.571(5) . ? C2 H2 1.0000 . ? C3 C4 1.520(5) . ? C3 C8 1.584(5) . ? C3 H3 1.0000 . ? C4 C5 1.542(5) . ? C4 H4 1.0000 . ? C5 C10 1.540(5) . ? C5 C6 1.548(5) . ? C5 H5 1.0000 . ? C6 C7 1.544(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.535(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.536(5) . ? C8 H8 1.0000 . ? C9 C14 1.559(5) . ? C9 C10 1.569(5) . ? C9 H9 1.0000 . ? C10 C11 1.543(5) . ? C10 H10 1.0000 . ? C11 C12 1.533(5) . ? C11 H11 1.0000 . ? C12 C13 1.547(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.527(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14 1.0000 . ? 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 C14 C1 C2 105.6(3) . . ? C14 C1 Br1 112.9(2) . . ? C2 C1 Br1 114.7(2) . . ? C14 C1 H1 107.8 . . ? C2 C1 H1 107.8 . . ? Br1 C1 H1 107.8 . . ? C1 C2 C11 108.7(3) . . ? C1 C2 C3 104.2(3) . . ? C11 C2 C3 108.7(3) . . ? C1 C2 H2 111.7 . . ? C11 C2 H2 111.7 . . ? C3 C2 H2 111.7 . . ? C4 C3 C2 110.4(3) . . ? C4 C3 C8 104.7(3) . . ? C2 C3 C8 107.4(3) . . ? C4 C3 H3 111.4 . . ? C2 C3 H3 111.4 . . ? C8 C3 H3 111.4 . . ? C3 C4 C5 105.6(3) . . ? C3 C4 Br2 113.9(2) . . ? C5 C4 Br2 114.1(3) . . ? C3 C4 H4 107.7 . . ? C5 C4 H4 107.7 . . ? Br2 C4 H4 107.7 . . ? C10 C5 C4 108.6(3) . . ? C10 C5 C6 109.3(3) . . ? C4 C5 C6 104.2(3) . . ? C10 C5 H5 111.5 . . ? C4 C5 H5 111.5 . . ? C6 C5 H5 111.5 . . ? C7 C6 C5 107.6(3) . . ? C7 C6 H6A 110.2 . . ? C5 C6 H6A 110.2 . . ? C7 C6 H6B 110.2 . . ? C5 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? C8 C7 C6 108.8(3) . . ? C8 C7 H7A 109.9 . . ? C6 C7 H7A 109.9 . . ? C8 C7 H7B 109.9 . . ? C6 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C7 C8 C9 108.2(3) . . ? C7 C8 C3 112.8(3) . . ? C9 C8 C3 104.1(3) . . ? C7 C8 H8 110.5 . . ? C9 C8 H8 110.5 . . ? C3 C8 H8 110.5 . . ? C8 C9 C14 111.3(3) . . ? C8 C9 C10 103.8(3) . . ? C14 C9 C10 109.8(3) . . ? C8 C9 H9 110.6 . . ? C14 C9 H9 110.6 . . ? C10 C9 H9 110.6 . . ? C5 C10 C11 110.7(3) . . ? C5 C10 C9 110.2(3) . . ? C11 C10 C9 103.7(3) . . ? C5 C10 H10 110.7 . . ? C11 C10 H10 110.7 . . ? C9 C10 H10 110.7 . . ? C12 C11 C10 108.5(3) . . ? C12 C11 C2 112.8(3) . . ? C10 C11 C2 103.9(3) . . ? C12 C11 H11 110.5 . . ? C10 C11 H11 110.5 . . ? C2 C11 H11 110.5 . . ? C11 C12 C13 108.5(3) . . ? C11 C12 H12A 110.0 . . ? C13 C12 H12A 110.0 . . ? C11 C12 H12B 110.0 . . ? C13 C12 H12B 110.0 . . ? H12A C12 H12B 108.4 . . ? C14 C13 C12 107.9(3) . . ? C14 C13 H13A 110.1 . . ? C12 C13 H13A 110.1 . . ? C14 C13 H13B 110.1 . . ? C12 C13 H13B 110.1 . . ? H13A C13 H13B 108.4 . . ? C1 C14 C13 111.2(3) . . ? C1 C14 C9 104.1(3) . . ? C13 C14 C9 109.7(3) . . ? C1 C14 H14 110.6 . . ? C13 C14 H14 110.6 . . ? C9 C14 H14 110.6 . . ? 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 C14 C1 C2 C11 -31.0(4) . . . . ? Br1 C1 C2 C11 93.9(3) . . . . ? C14 C1 C2 C3 84.7(3) . . . . ? Br1 C1 C2 C3 -150.4(2) . . . . ? C1 C2 C3 C4 -154.5(3) . . . . ? C11 C2 C3 C4 -38.7(4) . . . . ? C1 C2 C3 C8 -40.9(4) . . . . ? C11 C2 C3 C8 74.9(3) . . . . ? C2 C3 C4 C5 73.7(3) . . . . ? C8 C3 C4 C5 -41.7(4) . . . . ? C2 C3 C4 Br2 -52.3(3) . . . . ? C8 C3 C4 Br2 -167.6(2) . . . . ? C3 C4 C5 C10 -30.2(4) . . . . ? Br2 C4 C5 C10 95.7(3) . . . . ? C3 C4 C5 C6 86.3(4) . . . . ? Br2 C4 C5 C6 -147.9(3) . . . . ? C10 C5 C6 C7 69.4(4) . . . . ? C4 C5 C6 C7 -46.6(4) . . . . ? C5 C6 C7 C8 -22.4(4) . . . . ? C6 C7 C8 C9 -48.3(4) . . . . ? C6 C7 C8 C3 66.2(4) . . . . ? C4 C3 C8 C7 -29.5(4) . . . . ? C2 C3 C8 C7 -146.9(3) . . . . ? C4 C3 C8 C9 87.5(3) . . . . ? C2 C3 C8 C9 -29.9(4) . . . . ? C7 C8 C9 C14 -165.2(3) . . . . ? C3 C8 C9 C14 74.7(4) . . . . ? C7 C8 C9 C10 76.8(3) . . . . ? C3 C8 C9 C10 -43.3(4) . . . . ? C4 C5 C10 C11 -41.0(4) . . . . ? C6 C5 C10 C11 -154.2(3) . . . . ? C4 C5 C10 C9 73.1(3) . . . . ? C6 C5 C10 C9 -40.1(4) . . . . ? C8 C9 C10 C5 -28.4(4) . . . . ? C14 C9 C10 C5 -147.5(3) . . . . ? C8 C9 C10 C11 90.1(3) . . . . ? C14 C9 C10 C11 -29.0(4) . . . . ? C5 C10 C11 C12 -164.8(3) . . . . ? C9 C10 C11 C12 77.0(3) . . . . ? C5 C10 C11 C2 75.0(4) . . . . ? C9 C10 C11 C2 -43.2(3) . . . . ? C1 C2 C11 C12 -35.2(4) . . . . ? C3 C2 C11 C12 -148.0(3) . . . . ? C1 C2 C11 C10 82.0(3) . . . . ? C3 C2 C11 C10 -30.7(4) . . . . ? C10 C11 C12 C13 -48.2(4) . . . . ? C2 C11 C12 C13 66.3(4) . . . . ? C11 C12 C13 C14 -22.9(5) . . . . ? C2 C1 C14 C13 76.6(4) . . . . ? Br1 C1 C14 C13 -49.5(4) . . . . ? C2 C1 C14 C9 -41.4(4) . . . . ? Br1 C1 C14 C9 -167.5(2) . . . . ? C12 C13 C14 C1 -45.2(5) . . . . ? C12 C13 C14 C9 69.5(4) . . . . ? C8 C9 C14 C1 -34.8(4) . . . . ? C10 C9 C14 C1 79.6(3) . . . . ? C8 C9 C14 C13 -153.9(3) . . . . ? C10 C9 C14 C13 -39.5(4) . . . . ? _audit_block_code C14H18Br2_qo120_trauner _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C14 H18 Br2' _chemical_formula_sum 'C14 H18 Br2' _chemical_formula_weight 346.101 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 4 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.8730(2) _exptl_crystal_F_000 688 _database_code_depnum_ccdc_archive 'CCDC 948946' ####################################################################### # # 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_rv142 #?# MeasurementCode _vrf_PLAT410_rv142 ; PROBLEM: Short Intra H...H Contact H1 .. H4A .. 1.84 Ang. RESPONSE: All hydrogen positions have not been refined but included by constraints. ; _audit_update_record 25-Apr-13 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _exptl_crystal_description block #?# e.g.: needle, platelet; prisma _exptl_crystal_colour colourless _exptl_crystal_size_max 0.167 #?# in millimeters _exptl_crystal_size_mid 0.097 #?# in millimeters _exptl_crystal_size_min 0.090 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_creation_date ? #?# style: 18-Aug-1998 _diffrn_ambient_temperature 100(2) #?# in K _diffrn_source_type 'Bruker TXS' _diffrn_source_power 2.5 #?# in kW _diffrn_source_voltage 50 #?# in kV _diffrn_source_current 50 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_collimation 0.8_mm _diffrn_measurement_device 'fixed-chi three-circle diffractometer' _diffrn_measurement_device_type 'Bruker D8Venture' _diffrn_measurement_method 'mix of phi and omega scans' _diffrn_detector_area_resol_mean 10.4167 _diffrn_special_details ? _diffrn_orient_matrix_type ? _diffrn_orient_matrix_UB_11 ? _diffrn_orient_matrix_UB_12 ? _diffrn_orient_matrix_UB_13 ? _diffrn_orient_matrix_UB_21 ? _diffrn_orient_matrix_UB_22 ? _diffrn_orient_matrix_UB_23 ? _diffrn_orient_matrix_UB_31 ? _diffrn_orient_matrix_UB_32 ? _diffrn_orient_matrix_UB_33 ? loop_ _reflns_scale_group_code _reflns_scale_meas_F ? ? _cell_length_a 14.3718(4) _cell_length_b 6.4978(2) _cell_length_c 12.7356(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.731(2) _cell_angle_gamma 90.00 _cell_volume 1185.26(6) _cell_measurement_temperature 100(2) #?# in K _cell_measurement_reflns_used 127 _cell_measurement_theta_min 3.6273 _cell_measurement_theta_max 26.5615 _cell_special_details ? _exptl_absorpt_coefficient_mu 6.808 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6207 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _diffrn_reflns_number 22884 #xl _diffrn_reflns_av_R_equivalents 0.0451 #xl _diffrn_reflns_av_sigmaI/netI 0.0278 #xl _diffrn_reflns_limit_h_min -19 #xl _diffrn_reflns_limit_h_max 19 #xl _diffrn_reflns_limit_k_min -8 #xl _diffrn_reflns_limit_k_max 8 #xl _diffrn_reflns_limit_l_min -16 #xl _diffrn_reflns_limit_l_max 16 #xl _diffrn_reflns_theta_min 3.21 #xl _diffrn_reflns_theta_max 28.41 #xl _diffrn_measured_fraction_theta_max 0.997 #xl _diffrn_reflns_theta_full 28.33 #xl _diffrn_measured_fraction_theta_full 0.997 #xl _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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' 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' _reflns_number_total 2948 #xl _reflns_number_gt 2534 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0248P)^2^+0.6269P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details ? #xl _refine_ls_abs_structure_Flack ? #xl _refine_ls_number_reflns 2948 #xl _refine_ls_number_parameters 145 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0334 #xl _refine_ls_R_factor_gt 0.0233 #xl _refine_ls_wR_factor_ref 0.0520 #xl _refine_ls_wR_factor_gt 0.0491 #xl _refine_ls_goodness_of_fit_ref 1.054 #xl _refine_ls_restrained_S_all 1.054 #xl _refine_ls_shift/su_max 0.001 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.508 #xl _refine_diff_density_min -0.342 #xl _refine_diff_density_rms 0.096 #xl _refine_special_details ? _computing_data_collection 'Bruker Instrument Service v3.0.21' _computing_cell_refinement 'APEX2 v2012.4-3 (Bruker AXS)' _computing_data_reduction 'SAINT V8.18C (Bruker AXS Inc., 2011)' _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement ; Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. ; _computing_molecular_graphics ? _computing_publication_material ? 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 0.372456(14) 0.65752(3) -0.011297(16) 0.01377(7) Uani 1 1 d . . . Br2 Br 0.082252(14) 0.52614(3) 0.403066(16) 0.01443(7) Uani 1 1 d . . . C1 C 0.27340(14) 0.5885(3) 0.08372(16) 0.0105(4) Uani 1 1 d . . . H1 H 0.2202 0.6843 0.0646 0.013 Uiso 1 1 calc R . . C2 C 0.30499(14) 0.6310(3) 0.19971(16) 0.0096(4) Uani 1 1 d . . . H2 H 0.3474 0.7532 0.2033 0.012 Uiso 1 1 calc R . . C3 C 0.21713(14) 0.6819(3) 0.26312(16) 0.0106(4) Uani 1 1 d . . . H3 H 0.2336 0.7978 0.3128 0.013 Uiso 1 1 calc R . . C4 C 0.12903(14) 0.7404(3) 0.19277(16) 0.0116(4) Uani 1 1 d . . . H4A H 0.1453 0.8452 0.1409 0.014 Uiso 1 1 calc R . . H4B H 0.0827 0.8019 0.2368 0.014 Uiso 1 1 calc R . . C5 C 0.08510(14) 0.5511(3) 0.13350(17) 0.0126(4) Uani 1 1 d . . . H5A H 0.0260 0.5153 0.1640 0.015 Uiso 1 1 calc R . . H5B H 0.0697 0.5885 0.0587 0.015 Uiso 1 1 calc R . . C6 C 0.14908(14) 0.3608(3) 0.13864(16) 0.0111(4) Uani 1 1 d . . . H6 H 0.1102 0.2406 0.1129 0.013 Uiso 1 1 calc R . . C7 C 0.23432(14) 0.3718(3) 0.07059(16) 0.0116(4) Uani 1 1 d . . . H7 H 0.2155 0.3403 -0.0050 0.014 Uiso 1 1 calc R . . C8 C 0.29920(15) 0.2040(3) 0.12109(16) 0.0126(4) Uani 1 1 d . . . H8 H 0.2738 0.0636 0.1039 0.015 Uiso 1 1 calc R . . C9 C 0.40398(15) 0.2145(3) 0.10628(18) 0.0147(4) Uani 1 1 d . . . H9A H 0.4146 0.2625 0.0345 0.018 Uiso 1 1 calc R . . H9B H 0.4336 0.0779 0.1180 0.018 Uiso 1 1 calc R . . C10 C 0.44363(15) 0.3716(3) 0.19070(17) 0.0136(4) Uani 1 1 d . . . H10A H 0.4911 0.3055 0.2404 0.016 Uiso 1 1 calc R . . H10B H 0.4728 0.4897 0.1568 0.016 Uiso 1 1 calc R . . C11 C 0.35950(14) 0.4439(3) 0.24899(17) 0.0112(4) Uani 1 1 d . . . H11 H 0.3793 0.4711 0.3248 0.013 Uiso 1 1 calc R . . C12 C 0.29419(14) 0.2533(3) 0.23840(16) 0.0113(4) Uani 1 1 d . . . H12 H 0.3174 0.1372 0.2850 0.014 Uiso 1 1 calc R . . C13 C 0.19170(15) 0.3080(3) 0.25256(16) 0.0114(4) Uani 1 1 d . . . H13 H 0.1583 0.1895 0.2827 0.014 Uiso 1 1 calc R . . C14 C 0.19603(14) 0.4912(3) 0.32678(16) 0.0113(4) Uani 1 1 d . . . H14 H 0.2498 0.4692 0.3805 0.014 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 Br1 0.01240(11) 0.01650(11) 0.01278(11) 0.00266(8) 0.00331(8) -0.00096(8) Br2 0.01258(11) 0.01913(12) 0.01214(11) -0.00019(8) 0.00447(8) 0.00018(8) C1 0.0070(9) 0.0139(10) 0.0109(10) 0.0008(8) 0.0027(8) -0.0006(8) C2 0.0095(9) 0.0087(9) 0.0105(10) -0.0006(8) -0.0002(8) -0.0025(8) C3 0.0107(10) 0.0096(10) 0.0115(10) -0.0011(8) 0.0005(8) -0.0002(8) C4 0.0107(10) 0.0117(10) 0.0125(10) 0.0012(8) 0.0011(8) -0.0001(8) C5 0.0091(10) 0.0159(10) 0.0126(10) 0.0008(8) -0.0010(8) -0.0008(8) C6 0.0102(10) 0.0106(10) 0.0123(10) -0.0025(8) 0.0013(8) -0.0041(8) C7 0.0106(10) 0.0145(10) 0.0096(10) -0.0020(8) -0.0002(8) -0.0019(8) C8 0.0149(10) 0.0080(9) 0.0154(10) -0.0012(8) 0.0044(8) -0.0013(8) C9 0.0139(10) 0.0115(10) 0.0189(11) -0.0015(9) 0.0031(9) 0.0020(9) C10 0.0089(10) 0.0149(10) 0.0169(11) -0.0001(8) 0.0012(8) 0.0021(8) C11 0.0095(10) 0.0110(10) 0.0129(10) 0.0007(8) -0.0002(8) 0.0013(8) C12 0.0118(10) 0.0093(10) 0.0130(10) 0.0018(8) 0.0012(8) -0.0004(8) C13 0.0124(10) 0.0087(10) 0.0131(10) -0.0006(8) 0.0019(8) -0.0016(8) C14 0.0085(10) 0.0156(10) 0.0100(10) 0.0008(8) 0.0019(8) 0.0014(8) 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 C1 1.9941(19) . ? Br2 C14 1.983(2) . ? C1 C7 1.520(3) . ? C1 C2 1.534(3) . ? C1 H1 1.0000 . ? C2 C11 1.551(3) . ? C2 C3 1.589(3) . ? C2 H2 1.0000 . ? C3 C14 1.525(3) . ? C3 C4 1.537(3) . ? C3 H3 1.0000 . ? C4 C5 1.550(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.539(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.559(3) . ? C6 C13 1.566(3) . ? C6 H6 1.0000 . ? C7 C8 1.541(3) . ? C7 H7 1.0000 . ? C8 C9 1.534(3) . ? C8 C12 1.536(3) . ? C8 H8 1.0000 . ? C9 C10 1.556(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.543(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.553(3) . ? C11 H11 1.0000 . ? C12 C13 1.540(3) . ? C12 H12 1.0000 . ? C13 C14 1.518(3) . ? C13 H13 1.0000 . ? C14 H14 1.0000 . ? 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 C7 C1 C2 110.49(17) . . ? C7 C1 Br1 114.68(14) . . ? C2 C1 Br1 111.99(13) . . ? C7 C1 H1 106.4 . . ? C2 C1 H1 106.4 . . ? Br1 C1 H1 106.4 . . ? C1 C2 C11 110.37(16) . . ? C1 C2 C3 110.02(16) . . ? C11 C2 C3 110.70(16) . . ? C1 C2 H2 108.6 . . ? C11 C2 H2 108.6 . . ? C3 C2 H2 108.6 . . ? C14 C3 C4 108.70(17) . . ? C14 C3 C2 107.61(16) . . ? C4 C3 C2 113.96(16) . . ? C14 C3 H3 108.8 . . ? C4 C3 H3 108.8 . . ? C2 C3 H3 108.8 . . ? C3 C4 C5 111.72(17) . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? C6 C5 C4 113.51(17) . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5B 108.9 . . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C5 C6 C7 115.69(17) . . ? C5 C6 C13 113.73(17) . . ? C7 C6 C13 105.06(16) . . ? C5 C6 H6 107.3 . . ? C7 C6 H6 107.3 . . ? C13 C6 H6 107.3 . . ? C1 C7 C8 113.85(17) . . ? C1 C7 C6 106.35(16) . . ? C8 C7 C6 102.23(16) . . ? C1 C7 H7 111.3 . . ? C8 C7 H7 111.3 . . ? C6 C7 H7 111.3 . . ? C9 C8 C12 103.62(17) . . ? C9 C8 C7 118.92(17) . . ? C12 C8 C7 100.55(16) . . ? C9 C8 H8 110.9 . . ? C12 C8 H8 110.9 . . ? C7 C8 H8 110.9 . . ? C8 C9 C10 104.56(16) . . ? C8 C9 H9A 110.8 . . ? C10 C9 H9A 110.8 . . ? C8 C9 H9B 110.8 . . ? C10 C9 H9B 110.8 . . ? H9A C9 H9B 108.9 . . ? C11 C10 C9 105.98(17) . . ? C11 C10 H10A 110.5 . . ? C9 C10 H10A 110.5 . . ? C11 C10 H10B 110.5 . . ? C9 C10 H10B 110.5 . . ? H10A C10 H10B 108.7 . . ? C10 C11 C2 115.69(17) . . ? C10 C11 C12 101.97(16) . . ? C2 C11 C12 107.97(17) . . ? C10 C11 H11 110.3 . . ? C2 C11 H11 110.3 . . ? C12 C11 H11 110.3 . . ? C8 C12 C13 106.51(17) . . ? C8 C12 C11 100.04(16) . . ? C13 C12 C11 112.50(17) . . ? C8 C12 H12 112.3 . . ? C13 C12 H12 112.3 . . ? C11 C12 H12 112.3 . . ? C14 C13 C12 105.27(17) . . ? C14 C13 C6 113.43(17) . . ? C12 C13 C6 104.30(16) . . ? C14 C13 H13 111.2 . . ? C12 C13 H13 111.2 . . ? C6 C13 H13 111.2 . . ? C13 C14 C3 107.81(16) . . ? C13 C14 Br2 113.69(14) . . ? C3 C14 Br2 112.07(13) . . ? C13 C14 H14 107.7 . . ? C3 C14 H14 107.7 . . ? Br2 C14 H14 107.7 . . ? 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 C7 C1 C2 C11 43.8(2) . . . . ? Br1 C1 C2 C11 -85.35(17) . . . . ? C7 C1 C2 C3 -78.6(2) . . . . ? Br1 C1 C2 C3 152.19(13) . . . . ? C1 C2 C3 C14 103.29(19) . . . . ? C11 C2 C3 C14 -19.0(2) . . . . ? C1 C2 C3 C4 -17.3(2) . . . . ? C11 C2 C3 C4 -139.57(17) . . . . ? C14 C3 C4 C5 -47.4(2) . . . . ? C2 C3 C4 C5 72.6(2) . . . . ? C3 C4 C5 C6 -12.5(2) . . . . ? C4 C5 C6 C7 -72.7(2) . . . . ? C4 C5 C6 C13 49.1(2) . . . . ? C2 C1 C7 C8 -51.2(2) . . . . ? Br1 C1 C7 C8 76.49(19) . . . . ? C2 C1 C7 C6 60.6(2) . . . . ? Br1 C1 C7 C6 -171.73(13) . . . . ? C5 C6 C7 C1 41.5(2) . . . . ? C13 C6 C7 C1 -84.76(19) . . . . ? C5 C6 C7 C8 161.18(17) . . . . ? C13 C6 C7 C8 34.9(2) . . . . ? C1 C7 C8 C9 -43.5(2) . . . . ? C6 C7 C8 C9 -157.74(18) . . . . ? C1 C7 C8 C12 68.6(2) . . . . ? C6 C7 C8 C12 -45.62(19) . . . . ? C12 C8 C9 C10 -28.8(2) . . . . ? C7 C8 C9 C10 81.6(2) . . . . ? C8 C9 C10 C11 -0.3(2) . . . . ? C9 C10 C11 C2 -88.1(2) . . . . ? C9 C10 C11 C12 28.8(2) . . . . ? C1 C2 C11 C10 54.8(2) . . . . ? C3 C2 C11 C10 176.81(17) . . . . ? C1 C2 C11 C12 -58.7(2) . . . . ? C3 C2 C11 C12 63.4(2) . . . . ? C9 C8 C12 C13 163.81(16) . . . . ? C7 C8 C12 C13 40.36(19) . . . . ? C9 C8 C12 C11 46.56(19) . . . . ? C7 C8 C12 C11 -76.89(18) . . . . ? C10 C11 C12 C8 -46.00(19) . . . . ? C2 C11 C12 C8 76.33(19) . . . . ? C10 C11 C12 C13 -158.68(17) . . . . ? C2 C11 C12 C13 -36.4(2) . . . . ? C8 C12 C13 C14 -138.40(17) . . . . ? C11 C12 C13 C14 -29.8(2) . . . . ? C8 C12 C13 C6 -18.7(2) . . . . ? C11 C12 C13 C6 89.89(19) . . . . ? C5 C6 C13 C14 -23.6(2) . . . . ? C7 C6 C13 C14 103.91(19) . . . . ? C5 C6 C13 C12 -137.57(17) . . . . ? C7 C6 C13 C12 -10.1(2) . . . . ? C12 C13 C14 C3 78.1(2) . . . . ? C6 C13 C14 C3 -35.3(2) . . . . ? C12 C13 C14 Br2 -157.02(13) . . . . ? C6 C13 C14 Br2 89.57(18) . . . . ? C4 C3 C14 C13 73.5(2) . . . . ? C2 C3 C14 C13 -50.4(2) . . . . ? C4 C3 C14 Br2 -52.36(19) . . . . ? C2 C3 C14 Br2 -176.23(13) . . . . ? _audit_block_code C14H18Br2_rv142_trauner _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C14 H18 Br2' _chemical_formula_sum 'C14 H18 Br2' _chemical_formula_weight 346.101 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 4 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.93956(10) _exptl_crystal_F_000 688 _database_code_depnum_ccdc_archive 'CCDC 948947' ####################################################################### # # 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_ds _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C41 H32 Co2 F2 N6 O11, H2 O' _chemical_formula_sum 'C41 H34 Co2 F2 N6 O12' _chemical_formula_weight 958.60 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2431(9) _cell_length_b 14.06540(10) _cell_length_c 14.0892(2) _cell_angle_alpha 93.793(5) _cell_angle_beta 90.314(8) _cell_angle_gamma 93.311(8) _cell_volume 2021.96(18) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 980 _exptl_absorpt_coefficient_mu 0.902 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8058 _exptl_absorpt_correction_T_max 0.8472 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10880 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.1132 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7012 _reflns_number_gt 4226 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1208P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7012 _refine_ls_number_parameters 572 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1328 _refine_ls_R_factor_gt 0.0773 _refine_ls_wR_factor_ref 0.2290 _refine_ls_wR_factor_gt 0.1912 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.060 _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 Co1 Co 0.0000 0.5000 0.5000 0.0281(4) Uani 1 2 d S . . Co2 Co -0.25881(9) 0.60718(6) 0.55535(7) 0.0316(3) Uani 1 1 d . . . Co3 Co 0.0000 1.0000 1.0000 0.0349(4) Uani 1 2 d S . . F1 F 0.5244(7) 0.8719(6) 1.3301(5) 0.116(2) Uani 1 1 d U . . F2 F 0.4623(6) 0.6141(4) 1.1024(4) 0.0819(18) Uani 1 1 d . . . N1 N 0.6185(6) 0.6125(4) 0.6718(5) 0.0381(15) Uani 1 1 d . . . N2 N 0.4616(6) 0.5778(5) 0.7756(5) 0.0506(18) Uani 1 1 d . . . N3 N 0.5624(6) 0.6302(4) 0.8188(5) 0.0410(16) Uani 1 1 d . . . N4 N 0.2348(6) 0.7630(4) 0.9719(5) 0.0406(16) Uani 1 1 d . . . N5 N 0.1966(7) 0.7535(5) 1.0637(6) 0.062(2) Uani 1 1 d . . . N6 N 0.1164(6) 0.8824(4) 1.0076(4) 0.0409(16) Uani 1 1 d . . . O1 O 0.4915(5) 0.8101(4) 0.8870(4) 0.0481(14) Uani 1 1 d . . . H1 H 0.5703 0.8204 0.8797 0.072 Uiso 1 1 calc R . . O2 O -0.1625(5) 0.9247(4) 1.0606(4) 0.0504(14) Uani 1 1 d . . . H2B H -0.2046 0.9747 1.0707 0.060 Uiso 1 1 d R . . H2C H -0.2006 0.9087 1.0077 0.060 Uiso 1 1 d R . . O3 O -0.0658(5) 0.9504(4) 0.8603(4) 0.0417(13) Uani 1 1 d . . . O4 O -0.2499(5) 0.8696(5) 0.8850(4) 0.0591(17) Uani 1 1 d . . . O5 O -0.1215(5) 0.6852(3) 0.6302(4) 0.0376(12) Uani 1 1 d . . . O6 O 0.0581(5) 0.6129(3) 0.5886(4) 0.0377(12) Uani 1 1 d . . . O7 O -0.3837(5) 0.6615(3) 0.4676(4) 0.0461(14) Uani 1 1 d . . . H7B H -0.3677 0.6533 0.5257 0.055 Uiso 1 1 d R . . H7C H -0.4596 0.6364 0.4541 0.055 Uiso 1 1 d R . . O8 O -0.3773(5) 0.4266(4) 0.5374(4) 0.0451(14) Uani 1 1 d . . . O9 O -0.1787(4) 0.4825(3) 0.5741(3) 0.0310(11) Uani 1 1 d . . . O10 O 0.1261(4) 0.4061(3) 0.5668(3) 0.0343(12) Uani 1 1 d . . . O11 O 0.2411(6) 0.3472(5) 0.6798(5) 0.076(2) Uani 1 1 d . . . O12 O 0.8252(9) 0.7439(7) 0.1463(8) 0.152(4) Uani 1 1 d U . . H12A H 0.8201 0.8028 0.1374 0.183 Uiso 1 1 d R . . H12B H 0.8006 0.7340 0.2025 0.183 Uiso 1 1 d R . . C1 C 0.5006(7) 0.5707(6) 0.6873(6) 0.050(2) Uani 1 1 d . . . H1A H 0.4500 0.5388 0.6388 0.060 Uiso 1 1 calc R . . C2 C 0.6533(8) 0.6503(5) 0.7564(6) 0.044(2) Uani 1 1 d . . . H2A H 0.7310 0.6862 0.7702 0.052 Uiso 1 1 calc R . . C3 C 0.5615(8) 0.6564(6) 0.9192(6) 0.049(2) Uani 1 1 d . . . H3A H 0.6496 0.6773 0.9399 0.059 Uiso 1 1 calc R . . H3B H 0.5352 0.6005 0.9527 0.059 Uiso 1 1 calc R . . C4 C 0.4707(8) 0.7349(5) 0.9462(5) 0.0378(18) Uani 1 1 d . . . C5 C 0.4899(7) 0.7693(6) 1.0496(5) 0.0413(19) Uani 1 1 d . . . C6 C 0.5057(9) 0.8655(7) 1.0773(7) 0.062(3) Uani 1 1 d . . . H6 H 0.5101 0.9084 1.0299 0.074 Uiso 1 1 calc R . . C7 C 0.5152(10) 0.9010(9) 1.1682(9) 0.078(3) Uani 1 1 d . . . H7A H 0.5255 0.9664 1.1831 0.093 Uiso 1 1 calc R . . C8 C 0.5093(11) 0.8407(11) 1.2350(9) 0.084(3) Uani 1 1 d U . . C9 C 0.4970(9) 0.7426(11) 1.2204(7) 0.086(4) Uani 1 1 d . . . H9 H 0.4969 0.7016 1.2696 0.103 Uiso 1 1 calc R . . C10 C 0.4847(9) 0.7104(8) 1.1233(7) 0.060(3) Uani 1 1 d . . . C11 C 0.3268(7) 0.6992(5) 0.9283(6) 0.0413(19) Uani 1 1 d . . . H11A H 0.3103 0.6922 0.8602 0.050 Uiso 1 1 calc R . . H11B H 0.3126 0.6368 0.9531 0.050 Uiso 1 1 calc R . . C12 C 0.1273(10) 0.8276(7) 1.0797(7) 0.063(3) Uani 1 1 d . . . H12 H 0.0881 0.8411 1.1380 0.076 Uiso 1 1 calc R . . C13 C 0.1864(8) 0.8414(5) 0.9418(6) 0.044(2) Uani 1 1 d . . . H13 H 0.2007 0.8640 0.8820 0.052 Uiso 1 1 calc R . . C14 C -0.1679(8) 0.9048(5) 0.8311(5) 0.0376(18) Uani 1 1 d . . . C15 C -0.1967(7) 0.8971(5) 0.7266(5) 0.0336(17) Uani 1 1 d . . . C16 C -0.3238(8) 0.9085(5) 0.6974(6) 0.045(2) Uani 1 1 d . . . H16 H -0.3868 0.9190 0.7436 0.054 Uiso 1 1 calc R . . C17 C -0.3606(9) 0.9052(6) 0.6046(6) 0.053(2) Uani 1 1 d . . . H17 H -0.4471 0.9137 0.5884 0.064 Uiso 1 1 calc R . . C18 C -0.2720(9) 0.8896(5) 0.5359(7) 0.054(2) Uani 1 1 d . . . H18 H -0.2963 0.8882 0.4721 0.065 Uiso 1 1 calc R . . C19 C -0.1429(8) 0.8756(5) 0.5620(6) 0.046(2) Uani 1 1 d . . . H19 H -0.0818 0.8641 0.5146 0.055 Uiso 1 1 calc R . . C20 C -0.1036(8) 0.8783(5) 0.6564(5) 0.0351(17) Uani 1 1 d . . . C21 C 0.0343(7) 0.8591(5) 0.6753(5) 0.0325(16) Uani 1 1 d . . . C22 C 0.1218(8) 0.9364(6) 0.6981(6) 0.048(2) Uani 1 1 d . . . H22 H 0.0913 0.9974 0.7064 0.058 Uiso 1 1 calc R . . C23 C 0.2518(9) 0.9240(7) 0.7086(6) 0.058(2) Uani 1 1 d . . . H23 H 0.3095 0.9768 0.7215 0.070 Uiso 1 1 calc R . . C24 C 0.2989(8) 0.8335(6) 0.7002(5) 0.049(2) Uani 1 1 d . . . H24 H 0.3871 0.8248 0.7103 0.058 Uiso 1 1 calc R . . C25 C 0.2134(7) 0.7572(6) 0.6769(5) 0.0428(19) Uani 1 1 d . . . H25 H 0.2446 0.6963 0.6710 0.051 Uiso 1 1 calc R . . C26 C 0.0824(7) 0.7681(5) 0.6618(5) 0.0317(16) Uani 1 1 d . . . C27 C 0.0003(7) 0.6825(5) 0.6242(5) 0.0305(16) Uani 1 1 d . . . C28 C 0.1449(7) 0.3901(6) 0.6524(6) 0.0406(19) Uani 1 1 d . . . C29 C 0.0524(7) 0.4262(6) 0.7253(5) 0.0406(19) Uani 1 1 d . . . C30 C 0.0973(9) 0.4969(7) 0.7932(6) 0.059(2) Uani 1 1 d . . . H30 H 0.1848 0.5185 0.7931 0.071 Uiso 1 1 calc R . . C31 C 0.0160(10) 0.5357(8) 0.8604(7) 0.069(3) Uani 1 1 d . . . H31 H 0.0470 0.5836 0.9049 0.083 Uiso 1 1 calc R . . C32 C -0.1137(9) 0.5013(7) 0.8602(6) 0.063(3) Uani 1 1 d . . . H32 H -0.1705 0.5259 0.9056 0.075 Uiso 1 1 calc R . . C33 C -0.1591(8) 0.4315(6) 0.7935(6) 0.047(2) Uani 1 1 d . . . H33 H -0.2464 0.4095 0.7941 0.056 Uiso 1 1 calc R . . C34 C -0.0756(7) 0.3929(5) 0.7242(5) 0.0377(18) Uani 1 1 d . . . C35 C -0.1271(7) 0.3104(5) 0.6603(5) 0.0357(18) Uani 1 1 d . . . C36 C -0.0860(9) 0.2200(6) 0.6713(7) 0.054(2) Uani 1 1 d . . . H36 H -0.0182 0.2123 0.7138 0.065 Uiso 1 1 calc R . . C37 C -0.1417(10) 0.1419(6) 0.6217(7) 0.062(3) Uani 1 1 d . . . H37 H -0.1103 0.0822 0.6298 0.074 Uiso 1 1 calc R . . C38 C -0.2460(10) 0.1501(6) 0.5585(7) 0.059(3) Uani 1 1 d . . . H38 H -0.2863 0.0966 0.5257 0.071 Uiso 1 1 calc R . . C39 C -0.2858(8) 0.2387(5) 0.5469(6) 0.045(2) Uani 1 1 d . . . H39 H -0.3556 0.2452 0.5058 0.054 Uiso 1 1 calc R . . C40 C -0.2289(7) 0.3185(5) 0.5925(5) 0.0330(17) Uani 1 1 d . . . C41 C -0.2673(7) 0.4140(5) 0.5663(5) 0.0349(18) 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 Co1 0.0189(7) 0.0273(7) 0.0379(8) -0.0032(6) 0.0010(6) 0.0055(5) Co2 0.0208(5) 0.0313(5) 0.0424(7) -0.0036(4) -0.0014(4) 0.0064(4) Co3 0.0265(8) 0.0430(8) 0.0348(9) -0.0043(6) -0.0012(6) 0.0069(6) F1 0.100(4) 0.158(4) 0.082(4) -0.030(3) -0.004(3) -0.009(4) F2 0.096(5) 0.087(4) 0.067(4) 0.026(3) 0.014(3) 0.014(4) N1 0.029(4) 0.039(3) 0.046(4) -0.010(3) 0.003(3) 0.002(3) N2 0.036(4) 0.057(4) 0.057(5) -0.010(4) 0.013(3) -0.004(3) N3 0.026(4) 0.049(4) 0.048(4) -0.006(3) 0.003(3) 0.006(3) N4 0.034(4) 0.043(4) 0.045(4) 0.001(3) 0.002(3) 0.009(3) N5 0.049(5) 0.077(5) 0.067(6) 0.027(4) 0.023(4) 0.031(4) N6 0.041(4) 0.054(4) 0.028(4) -0.002(3) 0.001(3) 0.017(3) O1 0.033(3) 0.060(3) 0.052(4) 0.009(3) 0.000(3) 0.002(3) O2 0.032(3) 0.071(4) 0.048(4) 0.002(3) -0.001(3) 0.004(3) O3 0.037(3) 0.049(3) 0.037(3) -0.009(2) -0.001(2) 0.002(3) O4 0.040(3) 0.088(4) 0.047(4) 0.011(3) -0.005(3) -0.018(3) O5 0.025(3) 0.033(3) 0.054(4) -0.009(2) -0.002(2) 0.002(2) O6 0.032(3) 0.034(3) 0.046(3) -0.010(2) -0.006(2) 0.010(2) O7 0.025(3) 0.052(3) 0.062(4) 0.009(3) -0.017(2) 0.003(2) O8 0.021(3) 0.050(3) 0.063(4) -0.004(3) -0.009(2) 0.009(2) O9 0.024(3) 0.024(2) 0.045(3) -0.001(2) 0.004(2) 0.003(2) O10 0.020(3) 0.049(3) 0.035(3) 0.007(2) -0.001(2) 0.011(2) O11 0.043(4) 0.129(6) 0.063(4) 0.042(4) 0.005(3) 0.034(4) O12 0.123(7) 0.186(8) 0.159(7) 0.109(6) -0.016(6) 0.002(6) C1 0.023(4) 0.060(5) 0.063(6) -0.016(5) 0.000(4) -0.001(4) C2 0.034(5) 0.048(5) 0.047(5) -0.012(4) 0.002(4) 0.003(4) C3 0.041(5) 0.068(6) 0.040(5) -0.001(4) 0.002(4) 0.024(4) C4 0.042(5) 0.041(4) 0.030(4) -0.002(3) -0.002(3) 0.008(4) C5 0.029(4) 0.062(5) 0.033(5) -0.001(4) -0.001(3) 0.007(4) C6 0.052(6) 0.071(6) 0.058(6) -0.020(5) -0.006(5) 0.000(5) C7 0.048(6) 0.105(9) 0.074(8) -0.031(7) -0.002(5) -0.003(6) C8 0.062(6) 0.126(8) 0.056(6) -0.033(6) -0.002(5) -0.007(6) C9 0.039(6) 0.181(13) 0.041(6) 0.035(7) 0.000(4) 0.007(7) C10 0.048(6) 0.088(7) 0.046(6) 0.007(5) 0.006(4) 0.010(5) C11 0.032(4) 0.042(4) 0.050(5) 0.000(4) 0.004(4) 0.008(3) C12 0.072(7) 0.076(6) 0.046(6) 0.013(5) 0.023(5) 0.031(5) C13 0.046(5) 0.052(5) 0.034(5) 0.006(4) 0.008(4) 0.016(4) C14 0.040(5) 0.036(4) 0.035(5) -0.002(3) -0.009(4) 0.001(4) C15 0.038(4) 0.025(4) 0.036(4) -0.008(3) -0.007(3) -0.001(3) C16 0.036(5) 0.042(4) 0.057(6) 0.005(4) -0.001(4) 0.004(4) C17 0.047(5) 0.061(6) 0.052(6) 0.003(5) -0.020(5) 0.001(4) C18 0.069(7) 0.043(5) 0.049(6) 0.000(4) -0.027(5) -0.004(4) C19 0.053(5) 0.037(4) 0.046(5) 0.000(4) 0.001(4) -0.002(4) C20 0.048(5) 0.026(4) 0.031(4) -0.004(3) -0.009(3) 0.000(3) C21 0.029(4) 0.036(4) 0.031(4) -0.004(3) -0.001(3) -0.005(3) C22 0.054(6) 0.043(5) 0.045(5) -0.007(4) -0.005(4) -0.006(4) C23 0.045(6) 0.072(6) 0.054(6) -0.003(5) -0.007(4) -0.026(5) C24 0.037(5) 0.072(6) 0.034(5) -0.009(4) -0.006(4) -0.012(4) C25 0.032(4) 0.058(5) 0.038(5) -0.001(4) -0.001(3) 0.003(4) C26 0.022(4) 0.038(4) 0.034(4) -0.003(3) 0.000(3) 0.000(3) C27 0.035(4) 0.029(4) 0.028(4) -0.002(3) -0.003(3) 0.006(3) C28 0.023(4) 0.057(5) 0.044(5) 0.013(4) -0.001(3) 0.005(4) C29 0.033(4) 0.052(5) 0.038(5) 0.007(4) 0.003(3) 0.002(4) C30 0.040(5) 0.079(6) 0.056(6) -0.006(5) -0.005(4) -0.010(5) C31 0.056(6) 0.094(8) 0.053(6) -0.012(5) -0.002(5) -0.005(6) C32 0.056(6) 0.089(7) 0.043(6) -0.011(5) 0.010(5) 0.016(5) C33 0.030(4) 0.070(6) 0.039(5) -0.003(4) 0.002(4) 0.005(4) C34 0.031(4) 0.043(4) 0.039(5) 0.011(4) -0.007(3) 0.001(3) C35 0.027(4) 0.043(4) 0.037(5) 0.006(4) 0.007(3) 0.001(3) C36 0.049(5) 0.051(5) 0.066(6) 0.024(5) -0.001(5) 0.012(4) C37 0.077(7) 0.032(5) 0.078(7) 0.013(5) 0.007(6) 0.010(5) C38 0.080(7) 0.032(4) 0.065(7) 0.005(4) 0.004(5) -0.003(4) C39 0.049(5) 0.040(5) 0.045(5) 0.003(4) 0.009(4) -0.002(4) C40 0.026(4) 0.037(4) 0.036(4) 0.002(3) 0.002(3) -0.001(3) C41 0.036(5) 0.031(4) 0.037(5) -0.006(3) 0.008(4) 0.006(3) _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 Co1 O6 2.013(5) 2_566 ? Co1 O6 2.013(5) . ? Co1 O9 2.122(4) 2_566 ? Co1 O9 2.122(4) . ? Co1 O10 2.156(4) 2_566 ? Co1 O10 2.156(4) . ? Co2 O5 1.987(5) . ? Co2 O7 1.992(5) . ? Co2 O9 2.010(4) . ? Co2 N1 2.072(6) 1_455 ? Co2 O10 2.204(5) 2_566 ? Co2 H7B 1.3978 . ? Co3 N6 2.102(6) 2_577 ? Co3 N6 2.102(6) . ? Co3 O2 2.134(5) . ? Co3 O2 2.134(5) 2_577 ? Co3 O3 2.136(5) 2_577 ? Co3 O3 2.136(5) . ? F1 C8 1.387(12) . ? F2 C10 1.372(11) . ? N1 C2 1.311(10) . ? N1 C1 1.338(9) . ? N1 Co2 2.072(6) 1_655 ? N2 C1 1.309(10) . ? N2 N3 1.351(9) . ? N3 C2 1.316(9) . ? N3 C3 1.437(10) . ? N4 C13 1.329(9) . ? N4 N5 1.367(9) . ? N4 C11 1.449(9) . ? N5 C12 1.303(10) . ? N6 C13 1.300(9) . ? N6 C12 1.323(10) . ? O1 C4 1.396(9) . ? O1 H1 0.8200 . ? O2 H2B 0.8500 . ? O2 H2C 0.8500 . ? O3 C14 1.248(9) . ? O4 C14 1.240(9) . ? O5 C27 1.254(8) . ? O6 C27 1.252(8) . ? O7 H7B 0.8499 . ? O7 H7C 0.8500 . ? O8 C41 1.223(9) . ? O9 C41 1.283(8) . ? O10 C28 1.257(9) . ? O10 Co2 2.204(5) 2_566 ? O11 C28 1.257(9) . ? O12 H12A 0.8501 . ? O12 H12B 0.8500 . ? C1 H1A 0.9300 . ? C2 H2A 0.9300 . ? C3 C4 1.516(10) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.513(10) . ? C4 C11 1.543(10) . ? C5 C10 1.370(12) . ? C5 C6 1.382(11) . ? C6 C7 1.344(13) . ? C6 H6 0.9300 . ? C7 C8 1.308(16) . ? C7 H7A 0.9300 . ? C8 C9 1.380(16) . ? C9 C10 1.415(13) . ? C9 H9 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.496(10) . ? C15 C16 1.385(10) . ? C15 C20 1.400(10) . ? C16 C17 1.355(11) . ? C16 H16 0.9300 . ? C17 C18 1.346(12) . ? C17 H17 0.9300 . ? C18 C19 1.399(12) . ? C18 H18 0.9300 . ? C19 C20 1.385(10) . ? C19 H19 0.9300 . ? C20 C21 1.480(10) . ? C21 C22 1.388(10) . ? C21 C26 1.400(9) . ? C22 C23 1.361(12) . ? C22 H22 0.9300 . ? C23 C24 1.385(12) . ? C23 H23 0.9300 . ? C24 C25 1.367(10) . ? C24 H24 0.9300 . ? C25 C26 1.376(10) . ? C25 H25 0.9300 . ? C26 C27 1.494(10) . ? C28 C29 1.486(10) . ? C29 C34 1.366(10) . ? C29 C30 1.390(11) . ? C30 C31 1.371(12) . ? C30 H30 0.9300 . ? C31 C32 1.387(13) . ? C31 H31 0.9300 . ? C32 C33 1.372(12) . ? C32 H32 0.9300 . ? C33 C34 1.403(10) . ? C33 H33 0.9300 . ? C34 C35 1.491(11) . ? C35 C36 1.381(10) . ? C35 C40 1.424(10) . ? C36 C37 1.357(12) . ? C36 H36 0.9300 . ? C37 C38 1.402(13) . ? C37 H37 0.9300 . ? C38 C39 1.354(11) . ? C38 H38 0.9300 . ? C39 C40 1.356(10) . ? C39 H39 0.9300 . ? C40 C41 1.490(9) . ? 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 O6 Co1 O6 180.00(17) 2_566 . ? O6 Co1 O9 91.09(18) 2_566 2_566 ? O6 Co1 O9 88.91(18) . 2_566 ? O6 Co1 O9 88.91(18) 2_566 . ? O6 Co1 O9 91.09(18) . . ? O9 Co1 O9 180.000(1) 2_566 . ? O6 Co1 O10 93.03(19) 2_566 2_566 ? O6 Co1 O10 86.97(19) . 2_566 ? O9 Co1 O10 103.52(17) 2_566 2_566 ? O9 Co1 O10 76.48(17) . 2_566 ? O6 Co1 O10 86.97(19) 2_566 . ? O6 Co1 O10 93.03(19) . . ? O9 Co1 O10 76.48(17) 2_566 . ? O9 Co1 O10 103.52(17) . . ? O10 Co1 O10 180.000(1) 2_566 . ? O5 Co2 O7 123.6(2) . . ? O5 Co2 O9 94.4(2) . . ? O7 Co2 O9 139.2(2) . . ? O5 Co2 N1 90.1(2) . 1_455 ? O7 Co2 N1 95.2(2) . 1_455 ? O9 Co2 N1 99.3(2) . 1_455 ? O5 Co2 O10 90.48(19) . 2_566 ? O7 Co2 O10 86.9(2) . 2_566 ? O9 Co2 O10 77.71(18) . 2_566 ? N1 Co2 O10 177.0(2) 1_455 2_566 ? O5 Co2 H7B 117.6 . . ? O7 Co2 H7B 21.0 . . ? O9 Co2 H7B 147.2 . . ? N1 Co2 H7B 74.9 1_455 . ? O10 Co2 H7B 107.4 2_566 . ? N6 Co3 N6 180.000(2) 2_577 . ? N6 Co3 O2 88.3(2) 2_577 . ? N6 Co3 O2 91.7(2) . . ? N6 Co3 O2 91.7(2) 2_577 2_577 ? N6 Co3 O2 88.3(2) . 2_577 ? O2 Co3 O2 180.0(3) . 2_577 ? N6 Co3 O3 91.0(2) 2_577 2_577 ? N6 Co3 O3 89.0(2) . 2_577 ? O2 Co3 O3 89.5(2) . 2_577 ? O2 Co3 O3 90.5(2) 2_577 2_577 ? N6 Co3 O3 89.0(2) 2_577 . ? N6 Co3 O3 91.0(2) . . ? O2 Co3 O3 90.5(2) . . ? O2 Co3 O3 89.5(2) 2_577 . ? O3 Co3 O3 180.000(2) 2_577 . ? C2 N1 C1 102.8(7) . . ? C2 N1 Co2 124.2(5) . 1_655 ? C1 N1 Co2 132.4(6) . 1_655 ? C1 N2 N3 101.8(6) . . ? C2 N3 N2 110.1(7) . . ? C2 N3 C3 128.6(7) . . ? N2 N3 C3 121.3(6) . . ? C13 N4 N5 108.5(6) . . ? C13 N4 C11 130.9(7) . . ? N5 N4 C11 120.1(6) . . ? C12 N5 N4 101.8(7) . . ? C13 N6 C12 103.2(7) . . ? C13 N6 Co3 129.2(5) . . ? C12 N6 Co3 127.5(5) . . ? C4 O1 H1 109.5 . . ? Co3 O2 H2B 93.5 . . ? Co3 O2 H2C 95.1 . . ? H2B O2 H2C 94.1 . . ? C14 O3 Co3 131.9(5) . . ? C27 O5 Co2 128.5(4) . . ? C27 O6 Co1 133.0(5) . . ? Co2 O7 H7B 36.1 . . ? Co2 O7 H7C 123.8 . . ? H7B O7 H7C 108.0 . . ? C41 O9 Co2 109.9(4) . . ? C41 O9 Co1 129.6(4) . . ? Co2 O9 Co1 101.43(19) . . ? C28 O10 Co1 132.3(5) . . ? C28 O10 Co2 129.7(4) . 2_566 ? Co1 O10 Co2 94.41(19) . 2_566 ? H12A O12 H12B 108.9 . . ? N2 C1 N1 115.1(8) . . ? N2 C1 H1A 122.5 . . ? N1 C1 H1A 122.5 . . ? N1 C2 N3 110.2(7) . . ? N1 C2 H2A 124.9 . . ? N3 C2 H2A 124.9 . . ? N3 C3 C4 113.5(6) . . ? N3 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? N3 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? O1 C4 C5 111.0(6) . . ? O1 C4 C3 110.0(6) . . ? C5 C4 C3 110.6(6) . . ? O1 C4 C11 104.9(6) . . ? C5 C4 C11 109.7(6) . . ? C3 C4 C11 110.5(6) . . ? C10 C5 C6 114.5(8) . . ? C10 C5 C4 123.9(8) . . ? C6 C5 C4 121.4(7) . . ? C7 C6 C5 124.4(11) . . ? C7 C6 H6 117.8 . . ? C5 C6 H6 117.8 . . ? C8 C7 C6 117.9(12) . . ? C8 C7 H7A 121.1 . . ? C6 C7 H7A 121.1 . . ? C7 C8 C9 125.5(11) . . ? C7 C8 F1 121.1(13) . . ? C9 C8 F1 113.3(13) . . ? C8 C9 C10 113.5(10) . . ? C8 C9 H9 123.3 . . ? C10 C9 H9 123.3 . . ? C5 C10 F2 118.4(8) . . ? C5 C10 C9 124.1(11) . . ? F2 C10 C9 117.5(9) . . ? N4 C11 C4 112.9(6) . . ? N4 C11 H11A 109.0 . . ? C4 C11 H11A 109.0 . . ? N4 C11 H11B 109.0 . . ? C4 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? N5 C12 N6 115.7(8) . . ? N5 C12 H12 122.1 . . ? N6 C12 H12 122.1 . . ? N6 C13 N4 110.7(7) . . ? N6 C13 H13 124.6 . . ? N4 C13 H13 124.6 . . ? O4 C14 O3 123.0(7) . . ? O4 C14 C15 118.3(7) . . ? O3 C14 C15 118.6(7) . . ? C16 C15 C20 117.9(7) . . ? C16 C15 C14 117.9(7) . . ? C20 C15 C14 124.2(7) . . ? C17 C16 C15 123.0(8) . . ? C17 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? C18 C17 C16 120.0(8) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 119.0(8) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? C20 C19 C18 121.8(8) . . ? C20 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? C19 C20 C15 118.2(7) . . ? C19 C20 C21 116.9(7) . . ? C15 C20 C21 124.8(7) . . ? C22 C21 C26 118.7(7) . . ? C22 C21 C20 118.1(7) . . ? C26 C21 C20 122.9(6) . . ? C23 C22 C21 120.8(8) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C22 C23 C24 120.7(8) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C25 C24 C23 118.8(8) . . ? C25 C24 H24 120.6 . . ? C23 C24 H24 120.6 . . ? C24 C25 C26 121.8(8) . . ? C24 C25 H25 119.1 . . ? C26 C25 H25 119.1 . . ? C25 C26 C21 119.1(7) . . ? C25 C26 C27 117.7(6) . . ? C21 C26 C27 123.0(6) . . ? O6 C27 O5 124.4(7) . . ? O6 C27 C26 117.5(6) . . ? O5 C27 C26 118.0(6) . . ? O11 C28 O10 122.9(7) . . ? O11 C28 C29 118.1(7) . . ? O10 C28 C29 118.9(7) . . ? C34 C29 C30 120.3(7) . . ? C34 C29 C28 120.9(7) . . ? C30 C29 C28 118.8(7) . . ? C31 C30 C29 121.8(8) . . ? C31 C30 H30 119.1 . . ? C29 C30 H30 119.1 . . ? C30 C31 C32 118.1(9) . . ? C30 C31 H31 121.0 . . ? C32 C31 H31 121.0 . . ? C33 C32 C31 120.6(8) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C32 C33 C34 121.0(8) . . ? C32 C33 H33 119.5 . . ? C34 C33 H33 119.5 . . ? C29 C34 C33 118.3(7) . . ? C29 C34 C35 123.1(7) . . ? C33 C34 C35 118.3(7) . . ? C36 C35 C40 116.9(7) . . ? C36 C35 C34 120.4(7) . . ? C40 C35 C34 122.3(6) . . ? C37 C36 C35 121.8(9) . . ? C37 C36 H36 119.1 . . ? C35 C36 H36 119.1 . . ? C36 C37 C38 120.8(8) . . ? C36 C37 H37 119.6 . . ? C38 C37 H37 119.6 . . ? C39 C38 C37 117.5(9) . . ? C39 C38 H38 121.3 . . ? C37 C38 H38 121.3 . . ? C38 C39 C40 123.1(9) . . ? C38 C39 H39 118.4 . . ? C40 C39 H39 118.4 . . ? C39 C40 C35 119.7(7) . . ? C39 C40 C41 119.5(7) . . ? C35 C40 C41 120.7(7) . . ? O8 C41 O9 121.3(6) . . ? O8 C41 C40 121.8(7) . . ? O9 C41 C40 116.9(6) . . ? 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 O1 H1 O4 0.82 1.93 2.732(8) 166.2 1_655 O2 H2B N6 0.85 2.48 2.951(8) 115.5 2_577 O2 H2C O4 0.85 1.84 2.676(8) 168.6 . O7 H7B N1 0.85 2.18 3.003(8) 163.9 1_455 O7 H7C O8 0.85 1.85 2.677(7) 162.7 2_466 O12 H12A O2 0.85 2.09 2.883(10) 155.6 1_654 O12 H12B O11 0.85 2.11 2.905(11) 156.2 2_666 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.082 _refine_diff_density_min -0.818 _refine_diff_density_rms 0.138 _database_code_depnum_ccdc_archive 'CCDC 948948' ####################################################################### # # 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_rv255 #?# MeasurementCode _audit_update_record 12-Jul-13 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _exptl_crystal_description rod #?# e.g.: needle, platelet; prismati _exptl_crystal_colour colourless _exptl_crystal_size_max 0.096 #?# in millimeters _exptl_crystal_size_mid 0.049 #?# in millimeters _exptl_crystal_size_min 0.023 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_creation_date ? #?# style: 18-Aug-1998 _diffrn_ambient_temperature 123(2) #?# in K _diffrn_source_type 'Bruker TXS' _diffrn_source_power 2.5 #?# in kW _diffrn_source_voltage 50 #?# in kV _diffrn_source_current 50 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_collimation 0.8_mm _diffrn_measurement_device 'fixed-chi three-circle diffractometer' _diffrn_measurement_device_type 'Bruker D8Venture' _diffrn_measurement_method 'mix of phi and omega scans' _diffrn_detector_area_resol_mean 10.4167 _diffrn_special_details ? _diffrn_orient_matrix_type ? _diffrn_orient_matrix_UB_11 ? _diffrn_orient_matrix_UB_12 ? _diffrn_orient_matrix_UB_13 ? _diffrn_orient_matrix_UB_21 ? _diffrn_orient_matrix_UB_22 ? _diffrn_orient_matrix_UB_23 ? _diffrn_orient_matrix_UB_31 ? _diffrn_orient_matrix_UB_32 ? _diffrn_orient_matrix_UB_33 ? loop_ _reflns_scale_group_code _reflns_scale_meas_F ? ? _cell_length_a 7.0652(8) _cell_length_b 8.2217(9) _cell_length_c 13.0265(14) _cell_angle_alpha 92.900(3) _cell_angle_beta 90.127(3) _cell_angle_gamma 114.750(3) _cell_volume 686.07(13) _cell_measurement_temperature 123(2) #?# in K _cell_measurement_reflns_used 122 _cell_measurement_theta_min 3.1215 _cell_measurement_theta_max 38.5102 _cell_special_details ? _exptl_absorpt_coefficient_mu 0.840 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8682 _exptl_absorpt_correction_T_max 0.9582 _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _diffrn_reflns_number 9118 #xl _diffrn_reflns_av_R_equivalents 0.0629 #xl _diffrn_reflns_av_sigmaI/netI 0.0579 #xl _diffrn_reflns_limit_h_min -8 #xl _diffrn_reflns_limit_h_max 8 #xl _diffrn_reflns_limit_k_min -9 #xl _diffrn_reflns_limit_k_max 9 #xl _diffrn_reflns_limit_l_min -15 #xl _diffrn_reflns_limit_l_max 15 #xl _diffrn_reflns_theta_min 3.07 #xl _diffrn_reflns_theta_max 25.36 #xl _diffrn_measured_fraction_theta_max 0.996 #xl _diffrn_reflns_theta_full 25.42 #xl _diffrn_measured_fraction_theta_full 0.996 #xl _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _reflns_number_total 2522 #xl _reflns_number_gt 1889 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0277P)^2^+0.2364P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details ? #xl _refine_ls_abs_structure_Flack ? #xl _refine_ls_number_reflns 2522 #xl _refine_ls_number_parameters 163 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0615 #xl _refine_ls_R_factor_gt 0.0360 #xl _refine_ls_wR_factor_ref 0.0750 #xl _refine_ls_wR_factor_gt 0.0685 #xl _refine_ls_goodness_of_fit_ref 1.033 #xl _refine_ls_restrained_S_all 1.033 #xl _refine_ls_shift/su_max 0.000 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.361 #xl _refine_diff_density_min -0.284 #xl _refine_diff_density_rms 0.067 #xl _refine_special_details ? _computing_data_collection 'Bruker Instrument Service v3.0.21' _computing_cell_refinement 'APEX2 v2012.4-3 (Bruker AXS)' _computing_data_reduction 'SAINT V8.18C (Bruker AXS Inc., 2011)' _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement ; Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. ; _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4110(4) 0.7461(3) 0.15919(19) 0.0159(6) Uani 1 1 d . . . C2 C 0.5886(4) 0.7505(3) 0.22619(19) 0.0155(6) Uani 1 1 d . . . C3 C 0.5539(4) 0.7504(3) 0.32560(19) 0.0175(6) Uani 1 1 d . . . C4 C 0.3416(4) 0.7443(3) 0.35074(19) 0.0158(6) Uani 1 1 d . . . C5 C 0.3321(4) 0.9114(3) 0.3085(2) 0.0196(6) Uani 1 1 d . . . H5A H 0.4373 1.0207 0.3448 0.024 Uiso 1 1 calc R . . H5B H 0.1926 0.9093 0.3197 0.024 Uiso 1 1 calc R . . C6 C 0.3758(4) 0.9133(3) 0.1926(2) 0.0192(6) Uani 1 1 d . . . H6A H 0.2561 0.9138 0.1533 0.023 Uiso 1 1 calc R . . H6B H 0.5010 1.0230 0.1784 0.023 Uiso 1 1 calc R . . C7 C 0.2118(4) 0.5777(3) 0.17882(19) 0.0165(6) Uani 1 1 d . . . H7 H 0.0937 0.5891 0.1423 0.020 Uiso 1 1 calc R . . C8 C 0.1680(4) 0.5764(3) 0.29592(19) 0.0157(6) Uani 1 1 d . . . H8 H 0.0340 0.5890 0.3042 0.019 Uiso 1 1 calc R . . C9 C 0.1339(4) 0.3921(3) 0.3352(2) 0.0217(6) Uani 1 1 d . . . H9 H 0.1109 0.3887 0.4109 0.026 Uiso 1 1 calc R . . C10 C -0.0590(4) 0.2525(4) 0.2748(2) 0.0291(7) Uani 1 1 d . . . H10A H -0.0937 0.1317 0.2997 0.035 Uiso 1 1 calc R . . H10B H -0.1801 0.2816 0.2864 0.035 Uiso 1 1 calc R . . C11 C -0.0137(5) 0.2529(4) 0.1589(2) 0.0323(8) Uani 1 1 d . . . H11A H -0.1157 0.2812 0.1201 0.039 Uiso 1 1 calc R . . H11B H -0.0267 0.1330 0.1337 0.039 Uiso 1 1 calc R . . C12 C 0.2100(4) 0.3954(3) 0.1422(2) 0.0214(6) Uani 1 1 d . . . H12 H 0.2472 0.3950 0.0682 0.026 Uiso 1 1 calc R . . C13 C 0.3543(4) 0.3510(4) 0.2088(2) 0.0242(7) Uani 1 1 d . . . H13 H 0.4650 0.3265 0.1817 0.029 Uiso 1 1 calc R . . C14 C 0.3151(4) 0.3488(3) 0.3079(2) 0.0221(6) Uani 1 1 d . . . H14 H 0.3946 0.3222 0.3578 0.026 Uiso 1 1 calc R . . Cl1 Cl 0.46692(10) 0.75433(9) 0.02554(5) 0.02447(18) Uani 1 1 d . . . Cl2 Cl 0.80759(10) 0.74264(10) 0.17451(5) 0.02612(19) Uani 1 1 d . . . Cl3 Cl 0.72652(11) 0.74794(10) 0.41742(5) 0.0294(2) Uani 1 1 d . . . Cl4 Cl 0.29673(11) 0.74486(9) 0.48594(5) 0.02549(18) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0153(14) 0.0196(15) 0.0151(14) 0.0040(11) 0.0018(11) 0.0091(12) C2 0.0108(13) 0.0200(14) 0.0197(15) 0.0045(11) 0.0012(11) 0.0101(11) C3 0.0137(13) 0.0173(14) 0.0214(15) 0.0035(11) -0.0045(11) 0.0063(11) C4 0.0132(13) 0.0214(15) 0.0141(13) 0.0011(11) 0.0014(11) 0.0083(12) C5 0.0165(14) 0.0159(15) 0.0270(15) -0.0023(12) 0.0016(12) 0.0078(12) C6 0.0171(14) 0.0184(15) 0.0251(15) 0.0033(12) 0.0004(12) 0.0100(12) C7 0.0141(13) 0.0192(14) 0.0187(14) 0.0007(11) -0.0020(11) 0.0095(12) C8 0.0121(13) 0.0184(15) 0.0181(14) 0.0002(11) 0.0007(11) 0.0080(12) C9 0.0234(15) 0.0194(15) 0.0189(15) 0.0037(12) 0.0005(12) 0.0053(13) C10 0.0266(17) 0.0192(16) 0.0332(17) 0.0021(13) 0.0013(14) 0.0012(13) C11 0.0365(18) 0.0213(17) 0.0315(18) -0.0037(13) -0.0070(15) 0.0053(14) C12 0.0290(16) 0.0202(15) 0.0161(14) -0.0014(11) 0.0003(12) 0.0117(13) C13 0.0316(17) 0.0196(16) 0.0278(17) -0.0003(12) 0.0014(13) 0.0173(13) C14 0.0273(16) 0.0162(15) 0.0250(16) 0.0026(12) -0.0016(13) 0.0114(13) Cl1 0.0258(4) 0.0351(4) 0.0180(4) 0.0073(3) 0.0038(3) 0.0175(3) Cl2 0.0159(3) 0.0402(4) 0.0291(4) 0.0065(3) 0.0050(3) 0.0179(3) Cl3 0.0203(4) 0.0464(5) 0.0232(4) 0.0058(3) -0.0052(3) 0.0153(3) Cl4 0.0243(4) 0.0329(4) 0.0165(4) -0.0022(3) 0.0023(3) 0.0097(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.514(3) . ? C1 C6 1.538(3) . ? C1 C7 1.539(3) . ? C1 Cl1 1.785(3) . ? C2 C3 1.319(3) . ? C2 Cl2 1.713(2) . ? C3 C4 1.517(3) . ? C3 Cl3 1.713(2) . ? C4 C5 1.532(3) . ? C4 C8 1.549(3) . ? C4 Cl4 1.790(3) . ? C5 C6 1.541(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C12 1.544(4) . ? C7 C8 1.557(3) . ? C7 H7 1.0000 . ? C8 C9 1.545(3) . ? C8 H8 1.0000 . ? C9 C14 1.505(4) . ? C9 C10 1.545(4) . ? C9 H9 1.0000 . ? C10 C11 1.544(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.548(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.506(4) . ? C12 H12 1.0000 . ? C13 C14 1.320(4) . ? C13 H13 0.9500 . ? C14 H14 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 C2 C1 C6 106.5(2) . . ? C2 C1 C7 109.58(19) . . ? C6 C1 C7 108.8(2) . . ? C2 C1 Cl1 113.06(17) . . ? C6 C1 Cl1 108.40(16) . . ? C7 C1 Cl1 110.33(17) . . ? C3 C2 C1 114.3(2) . . ? C3 C2 Cl2 123.8(2) . . ? C1 C2 Cl2 121.76(18) . . ? C2 C3 C4 113.4(2) . . ? C2 C3 Cl3 123.5(2) . . ? C4 C3 Cl3 123.06(19) . . ? C3 C4 C5 107.2(2) . . ? C3 C4 C8 110.0(2) . . ? C5 C4 C8 108.3(2) . . ? C3 C4 Cl4 112.95(17) . . ? C5 C4 Cl4 108.73(17) . . ? C8 C4 Cl4 109.57(16) . . ? C4 C5 C6 108.8(2) . . ? C4 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? C4 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? C1 C6 C5 109.33(19) . . ? C1 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? C1 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.3 . . ? C1 C7 C12 116.6(2) . . ? C1 C7 C8 108.7(2) . . ? C12 C7 C8 109.1(2) . . ? C1 C7 H7 107.4 . . ? C12 C7 H7 107.4 . . ? C8 C7 H7 107.4 . . ? C9 C8 C4 117.0(2) . . ? C9 C8 C7 109.2(2) . . ? C4 C8 C7 108.62(19) . . ? C9 C8 H8 107.2 . . ? C4 C8 H8 107.2 . . ? C7 C8 H8 107.2 . . ? C14 C9 C10 107.0(2) . . ? C14 C9 C8 110.3(2) . . ? C10 C9 C8 106.0(2) . . ? C14 C9 H9 111.1 . . ? C10 C9 H9 111.1 . . ? C8 C9 H9 111.1 . . ? C11 C10 C9 109.9(2) . . ? C11 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? C11 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? C10 C11 C12 108.9(2) . . ? C10 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? C10 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? C13 C12 C7 110.5(2) . . ? C13 C12 C11 106.9(2) . . ? C7 C12 C11 106.1(2) . . ? C13 C12 H12 111.1 . . ? C7 C12 H12 111.1 . . ? C11 C12 H12 111.1 . . ? C14 C13 C12 114.8(2) . . ? C14 C13 H13 122.6 . . ? C12 C13 H13 122.6 . . ? C13 C14 C9 114.4(2) . . ? C13 C14 H14 122.8 . . ? C9 C14 H14 122.8 . . ? 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 C6 C1 C2 C3 59.0(3) . . . . ? C7 C1 C2 C3 -58.5(3) . . . . ? Cl1 C1 C2 C3 177.95(19) . . . . ? C6 C1 C2 Cl2 -124.7(2) . . . . ? C7 C1 C2 Cl2 117.8(2) . . . . ? Cl1 C1 C2 Cl2 -5.7(3) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? Cl2 C2 C3 C4 -175.75(18) . . . . ? C1 C2 C3 Cl3 177.92(18) . . . . ? Cl2 C2 C3 Cl3 1.7(3) . . . . ? C2 C3 C4 C5 -60.1(3) . . . . ? Cl3 C3 C4 C5 122.5(2) . . . . ? C2 C3 C4 C8 57.4(3) . . . . ? Cl3 C3 C4 C8 -120.0(2) . . . . ? C2 C3 C4 Cl4 -179.82(19) . . . . ? Cl3 C3 C4 Cl4 2.7(3) . . . . ? C3 C4 C5 C6 56.3(3) . . . . ? C8 C4 C5 C6 -62.3(3) . . . . ? Cl4 C4 C5 C6 178.71(17) . . . . ? C2 C1 C6 C5 -56.7(2) . . . . ? C7 C1 C6 C5 61.3(3) . . . . ? Cl1 C1 C6 C5 -178.71(17) . . . . ? C4 C5 C6 C1 0.7(3) . . . . ? C2 C1 C7 C12 -68.6(3) . . . . ? C6 C1 C7 C12 175.3(2) . . . . ? Cl1 C1 C7 C12 56.6(2) . . . . ? C2 C1 C7 C8 55.2(3) . . . . ? C6 C1 C7 C8 -60.9(2) . . . . ? Cl1 C1 C7 C8 -179.66(17) . . . . ? C3 C4 C8 C9 69.6(3) . . . . ? C5 C4 C8 C9 -173.6(2) . . . . ? Cl4 C4 C8 C9 -55.2(3) . . . . ? C3 C4 C8 C7 -54.6(2) . . . . ? C5 C4 C8 C7 62.2(2) . . . . ? Cl4 C4 C8 C7 -179.34(16) . . . . ? C1 C7 C8 C9 -129.1(2) . . . . ? C12 C7 C8 C9 -1.0(3) . . . . ? C1 C7 C8 C4 -0.4(3) . . . . ? C12 C7 C8 C4 127.7(2) . . . . ? C4 C8 C9 C14 -69.8(3) . . . . ? C7 C8 C9 C14 54.0(3) . . . . ? C4 C8 C9 C10 174.7(2) . . . . ? C7 C8 C9 C10 -61.4(3) . . . . ? C14 C9 C10 C11 -55.0(3) . . . . ? C8 C9 C10 C11 62.6(3) . . . . ? C9 C10 C11 C12 -0.6(3) . . . . ? C1 C7 C12 C13 71.1(3) . . . . ? C8 C7 C12 C13 -52.4(3) . . . . ? C1 C7 C12 C11 -173.4(2) . . . . ? C8 C7 C12 C11 63.1(3) . . . . ? C10 C11 C12 C13 55.8(3) . . . . ? C10 C11 C12 C7 -62.2(3) . . . . ? C7 C12 C13 C14 56.3(3) . . . . ? C11 C12 C13 C14 -58.7(3) . . . . ? C12 C13 C14 C9 -0.3(3) . . . . ? C10 C9 C14 C13 58.5(3) . . . . ? C8 C9 C14 C13 -56.2(3) . . . . ? _audit_block_code C14H14Cl4_rv255_trauner _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C14 H14 Cl4' _chemical_formula_sum 'C14 H14 Cl4' _chemical_formula_weight 324.072 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 2 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.5688(3) _exptl_crystal_F_000 332 _database_code_depnum_ccdc_archive 'CCDC 949955' ####################################################################### # # 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_rv254 #?# MeasurementCode _audit_update_record 12-Jul-13 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _exptl_crystal_description block #?# e.g.: needle, platelet; prisma _exptl_crystal_colour colourless _exptl_crystal_size_max 0.151 #?# in millimeters _exptl_crystal_size_mid 0.089 #?# in millimeters _exptl_crystal_size_min 0.081 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_creation_date ? #?# style: 18-Aug-1998 _diffrn_ambient_temperature 123(2) #?# in K _diffrn_source_type 'Bruker TXS' _diffrn_source_power 2.5 #?# in kW _diffrn_source_voltage 50 #?# in kV _diffrn_source_current 50 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_collimation 0.8_mm _diffrn_measurement_device 'fixed-chi three-circle diffractometer' _diffrn_measurement_device_type 'Bruker D8Venture' _diffrn_measurement_method 'mix of phi and omega scans' _diffrn_detector_area_resol_mean 10.4167 _diffrn_special_details ? _diffrn_orient_matrix_type ? _diffrn_orient_matrix_UB_11 ? _diffrn_orient_matrix_UB_12 ? _diffrn_orient_matrix_UB_13 ? _diffrn_orient_matrix_UB_21 ? _diffrn_orient_matrix_UB_22 ? _diffrn_orient_matrix_UB_23 ? _diffrn_orient_matrix_UB_31 ? _diffrn_orient_matrix_UB_32 ? _diffrn_orient_matrix_UB_33 ? loop_ _reflns_scale_group_code _reflns_scale_meas_F ? ? _cell_length_a 7.0286(4) _cell_length_b 8.7167(5) _cell_length_c 15.6853(9) _cell_angle_alpha 83.186(2) _cell_angle_beta 87.4669(19) _cell_angle_gamma 66.2540(16) _cell_volume 873.40(9) _cell_measurement_temperature 123(2) #?# in K _cell_measurement_reflns_used 122 _cell_measurement_theta_min 3.5380 _cell_measurement_theta_max 31.6774 _cell_special_details ? _exptl_absorpt_coefficient_mu 0.677 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9197 _exptl_absorpt_correction_T_max 0.9582 _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _diffrn_reflns_number 8310 #xl _diffrn_reflns_av_R_equivalents 0.0244 #xl _diffrn_reflns_av_sigmaI/netI 0.0296 #xl _diffrn_reflns_limit_h_min -8 #xl _diffrn_reflns_limit_h_max 8 #xl _diffrn_reflns_limit_k_min -10 #xl _diffrn_reflns_limit_k_max 10 #xl _diffrn_reflns_limit_l_min -18 #xl _diffrn_reflns_limit_l_max 18 #xl _diffrn_reflns_theta_min 3.17 #xl _diffrn_reflns_theta_max 25.03 #xl _diffrn_measured_fraction_theta_max 0.991 #xl _diffrn_reflns_theta_full 25.01 #xl _diffrn_measured_fraction_theta_full 0.991 #xl _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _reflns_number_total 3057 #xl _reflns_number_gt 2728 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0276P)^2^+0.7769P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details ? #xl _refine_ls_abs_structure_Flack ? #xl _refine_ls_number_reflns 3057 #xl _refine_ls_number_parameters 217 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0354 #xl _refine_ls_R_factor_gt 0.0299 #xl _refine_ls_wR_factor_ref 0.0766 #xl _refine_ls_wR_factor_gt 0.0744 #xl _refine_ls_goodness_of_fit_ref 1.116 #xl _refine_ls_restrained_S_all 1.116 #xl _refine_ls_shift/su_max 0.001 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.364 #xl _refine_diff_density_min -0.227 #xl _refine_diff_density_rms 0.059 #xl _refine_special_details ? _computing_data_collection 'Bruker Instrument Service v3.0.21' _computing_cell_refinement 'APEX2 v2012.4-3 (Bruker AXS)' _computing_data_reduction 'SAINT V8.18C (Bruker AXS Inc., 2011)' _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement ; Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. ; _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8107(3) -0.1128(2) 0.20493(13) 0.0123(4) Uani 1 1 d . . . C2 C 0.9994(3) -0.0739(3) 0.21728(13) 0.0130(4) Uani 1 1 d . . . C3 C 0.9642(3) 0.0462(3) 0.26750(13) 0.0132(4) Uani 1 1 d . . . C4 C 0.7467(3) 0.1177(2) 0.30247(13) 0.0114(4) Uani 1 1 d . . . C5 C 0.7032(3) -0.0286(3) 0.35376(13) 0.0125(4) Uani 1 1 d . . . H5 H 0.5535 0.0183 0.3708 0.015 Uiso 1 1 calc R . . C6 C 0.7339(3) -0.1660(2) 0.29329(13) 0.0128(4) Uani 1 1 d . . . H6 H 0.5937 -0.1650 0.2837 0.015 Uiso 1 1 calc R . . C7 C 0.8689(3) -0.3421(3) 0.33988(14) 0.0174(5) Uani 1 1 d . . . H7 H 0.8913 -0.4334 0.3027 0.021 Uiso 1 1 calc R . . C8 C 0.7478(4) -0.3631(3) 0.42211(14) 0.0203(5) Uani 1 1 d . . . H8A H 0.6062 -0.3488 0.4065 0.024 Uiso 1 1 calc R . . H8B H 0.8195 -0.4778 0.4522 0.024 Uiso 1 1 calc R . . C9 C 0.7339(4) -0.2306(3) 0.48188(14) 0.0214(5) Uani 1 1 d . . . H9A H 0.8076 -0.2876 0.5365 0.026 Uiso 1 1 calc R . . H9B H 0.5865 -0.1633 0.4951 0.026 Uiso 1 1 calc R . . C10 C 0.8336(3) -0.1137(3) 0.43690(13) 0.0169(5) Uani 1 1 d . . . H10 H 0.8295 -0.0276 0.4746 0.020 Uiso 1 1 calc R . . C11 C 1.0547(3) -0.2257(3) 0.41628(14) 0.0201(5) Uani 1 1 d . . . H11 H 1.1715 -0.2122 0.4368 0.024 Uiso 1 1 calc R . . C12 C 1.0723(3) -0.3443(3) 0.36724(14) 0.0198(5) Uani 1 1 d . . . H12 H 1.2029 -0.4242 0.3507 0.024 Uiso 1 1 calc R . . C13 C 0.6301(3) 0.0500(2) 0.16678(13) 0.0122(4) Uani 1 1 d . . . H13 H 0.5027 0.0254 0.1687 0.015 Uiso 1 1 calc R . . C14 C 0.5903(3) 0.1901(2) 0.22668(13) 0.0122(4) Uani 1 1 d . . . H14 H 0.4484 0.2177 0.2515 0.015 Uiso 1 1 calc R . . C15 C 0.5855(3) 0.3520(3) 0.17146(14) 0.0171(5) Uani 1 1 d . . . H15 H 0.5665 0.4433 0.2082 0.021 Uiso 1 1 calc R . . C16 C 0.3990(4) 0.4039(3) 0.10928(15) 0.0223(5) Uani 1 1 d . . . H16A H 0.2705 0.4206 0.1426 0.027 Uiso 1 1 calc R . . H16B H 0.3793 0.5116 0.0744 0.027 Uiso 1 1 calc R . . C17 C 0.4403(4) 0.2653(3) 0.05004(14) 0.0223(5) Uani 1 1 d . . . H17A H 0.4402 0.3124 -0.0106 0.027 Uiso 1 1 calc R . . H17B H 0.3291 0.2226 0.0571 0.027 Uiso 1 1 calc R . . C18 C 0.6533(3) 0.1194(3) 0.07289(13) 0.0168(5) Uani 1 1 d . . . H18 H 0.6873 0.0300 0.0334 0.020 Uiso 1 1 calc R . . C19 C 0.8127(3) 0.1948(3) 0.06668(14) 0.0190(5) Uani 1 1 d . . . H19 H 0.9290 0.1595 0.0294 0.023 Uiso 1 1 calc R . . C20 C 0.7777(3) 0.3142(3) 0.11743(14) 0.0194(5) Uani 1 1 d . . . H20 H 0.8670 0.3715 0.1195 0.023 Uiso 1 1 calc R . . Cl1 Cl 0.86099(8) -0.27470(6) 0.13618(3) 0.01699(13) Uani 1 1 d . . . Cl2 Cl 1.23386(8) -0.17599(7) 0.16974(3) 0.02091(14) Uani 1 1 d . . . Cl3 Cl 1.14946(8) 0.11409(7) 0.29349(4) 0.02300(15) Uani 1 1 d . . . Cl4 Cl 0.70438(8) 0.27916(6) 0.37060(3) 0.01658(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0146(10) 0.0099(10) 0.0135(10) -0.0044(8) -0.0005(8) -0.0051(8) C2 0.0110(10) 0.0140(10) 0.0126(10) -0.0008(8) 0.0012(8) -0.0039(8) C3 0.0129(10) 0.0156(10) 0.0125(10) 0.0004(8) -0.0026(8) -0.0076(9) C4 0.0126(10) 0.0116(10) 0.0115(10) -0.0037(8) 0.0007(8) -0.0059(8) C5 0.0130(10) 0.0133(10) 0.0121(10) -0.0024(8) 0.0013(8) -0.0059(8) C6 0.0126(10) 0.0119(10) 0.0144(10) -0.0018(8) -0.0010(8) -0.0053(8) C7 0.0243(12) 0.0103(10) 0.0163(11) -0.0023(8) -0.0005(9) -0.0053(9) C8 0.0286(12) 0.0143(11) 0.0197(11) 0.0014(9) 0.0003(9) -0.0115(10) C9 0.0294(13) 0.0179(11) 0.0154(11) -0.0001(9) 0.0024(9) -0.0087(10) C10 0.0248(11) 0.0158(11) 0.0110(10) -0.0018(8) -0.0020(9) -0.0086(9) C11 0.0215(12) 0.0203(11) 0.0170(11) 0.0055(9) -0.0081(9) -0.0082(9) C12 0.0179(11) 0.0169(11) 0.0170(11) 0.0035(9) -0.0021(9) -0.0003(9) C13 0.0107(10) 0.0117(10) 0.0146(10) -0.0013(8) -0.0019(8) -0.0047(8) C14 0.0089(9) 0.0116(10) 0.0149(10) -0.0012(8) 0.0002(8) -0.0031(8) C15 0.0224(11) 0.0095(10) 0.0179(11) -0.0015(8) -0.0018(9) -0.0046(9) C16 0.0213(12) 0.0156(11) 0.0224(12) 0.0025(9) -0.0044(9) -0.0003(9) C17 0.0240(12) 0.0220(12) 0.0193(11) 0.0032(9) -0.0090(9) -0.0082(10) C18 0.0220(11) 0.0160(11) 0.0111(10) -0.0013(8) -0.0021(8) -0.0061(9) C19 0.0208(11) 0.0201(11) 0.0132(10) 0.0035(9) 0.0011(9) -0.0066(9) C20 0.0220(12) 0.0189(11) 0.0191(11) 0.0064(9) -0.0037(9) -0.0122(9) Cl1 0.0218(3) 0.0135(3) 0.0161(3) -0.0065(2) -0.0008(2) -0.0061(2) Cl2 0.0124(3) 0.0237(3) 0.0260(3) -0.0102(2) 0.0060(2) -0.0051(2) Cl3 0.0158(3) 0.0292(3) 0.0315(3) -0.0118(2) 0.0018(2) -0.0147(2) Cl4 0.0221(3) 0.0136(3) 0.0164(3) -0.0065(2) 0.0019(2) -0.0085(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.521(3) . ? C1 C13 1.549(3) . ? C1 C6 1.552(3) . ? C1 Cl1 1.7901(19) . ? C2 C3 1.322(3) . ? C2 Cl2 1.712(2) . ? C3 C4 1.505(3) . ? C3 Cl3 1.714(2) . ? C4 C14 1.549(3) . ? C4 C5 1.555(3) . ? C4 Cl4 1.7895(19) . ? C5 C10 1.555(3) . ? C5 C6 1.557(3) . ? C5 H5 1.0000 . ? C6 C7 1.554(3) . ? C6 H6 1.0000 . ? C7 C12 1.503(3) . ? C7 C8 1.547(3) . ? C7 H7 1.0000 . ? C8 C9 1.543(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.545(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.511(3) . ? C10 H10 1.0000 . ? C11 C12 1.324(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.552(3) . ? C13 C14 1.557(3) . ? C13 H13 1.0000 . ? C14 C15 1.554(3) . ? C14 H14 1.0000 . ? C15 C20 1.503(3) . ? C15 C16 1.551(3) . ? C15 H15 1.0000 . ? C16 C17 1.538(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.547(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.505(3) . ? C18 H18 1.0000 . ? C19 C20 1.323(3) . ? C19 H19 0.9500 . ? C20 H20 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 C2 C1 C13 109.09(16) . . ? C2 C1 C6 109.92(16) . . ? C13 C1 C6 106.20(16) . . ? C2 C1 Cl1 112.91(14) . . ? C13 C1 Cl1 109.24(13) . . ? C6 C1 Cl1 109.25(14) . . ? C3 C2 C1 113.58(17) . . ? C3 C2 Cl2 123.65(16) . . ? C1 C2 Cl2 122.77(15) . . ? C2 C3 C4 114.47(18) . . ? C2 C3 Cl3 123.63(16) . . ? C4 C3 Cl3 121.89(15) . . ? C3 C4 C14 109.13(16) . . ? C3 C4 C5 108.36(16) . . ? C14 C4 C5 107.41(16) . . ? C3 C4 Cl4 113.39(14) . . ? C14 C4 Cl4 109.14(13) . . ? C5 C4 Cl4 109.24(13) . . ? C4 C5 C10 116.60(17) . . ? C4 C5 C6 108.92(16) . . ? C10 C5 C6 108.90(16) . . ? C4 C5 H5 107.3 . . ? C10 C5 H5 107.3 . . ? C6 C5 H5 107.3 . . ? C1 C6 C7 117.58(17) . . ? C1 C6 C5 108.45(16) . . ? C7 C6 C5 109.20(16) . . ? C1 C6 H6 107.0 . . ? C7 C6 H6 107.0 . . ? C5 C6 H6 107.0 . . ? C12 C7 C8 107.65(17) . . ? C12 C7 C6 109.84(18) . . ? C8 C7 C6 105.63(17) . . ? C12 C7 H7 111.2 . . ? C8 C7 H7 111.2 . . ? C6 C7 H7 111.2 . . ? C9 C8 C7 109.82(18) . . ? C9 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? C9 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C8 C9 C10 109.11(17) . . ? C8 C9 H9A 109.9 . . ? C10 C9 H9A 109.9 . . ? C8 C9 H9B 109.9 . . ? C10 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? C11 C10 C9 106.67(18) . . ? C11 C10 C5 111.38(17) . . ? C9 C10 C5 105.35(17) . . ? C11 C10 H10 111.1 . . ? C9 C10 H10 111.1 . . ? C5 C10 H10 111.1 . . ? C12 C11 C10 114.5(2) . . ? C12 C11 H11 122.8 . . ? C10 C11 H11 122.8 . . ? C11 C12 C7 114.55(19) . . ? C11 C12 H12 122.7 . . ? C7 C12 H12 122.7 . . ? C1 C13 C18 117.36(17) . . ? C1 C13 C14 108.57(15) . . ? C18 C13 C14 109.33(16) . . ? C1 C13 H13 107.0 . . ? C18 C13 H13 107.0 . . ? C14 C13 H13 107.0 . . ? C4 C14 C15 117.30(17) . . ? C4 C14 C13 108.96(15) . . ? C15 C14 C13 108.89(16) . . ? C4 C14 H14 107.1 . . ? C15 C14 H14 107.1 . . ? C13 C14 H14 107.1 . . ? C20 C15 C16 107.23(18) . . ? C20 C15 C14 111.01(17) . . ? C16 C15 C14 104.89(17) . . ? C20 C15 H15 111.2 . . ? C16 C15 H15 111.2 . . ? C14 C15 H15 111.2 . . ? C17 C16 C15 109.59(17) . . ? C17 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? C17 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.2 . . ? C16 C17 C18 109.48(17) . . ? C16 C17 H17A 109.8 . . ? C18 C17 H17A 109.8 . . ? C16 C17 H17B 109.8 . . ? C18 C17 H17B 109.8 . . ? H17A C17 H17B 108.2 . . ? C19 C18 C17 107.05(18) . . ? C19 C18 C13 111.17(17) . . ? C17 C18 C13 104.95(17) . . ? C19 C18 H18 111.1 . . ? C17 C18 H18 111.1 . . ? C13 C18 H18 111.1 . . ? C20 C19 C18 114.5(2) . . ? C20 C19 H19 122.8 . . ? C18 C19 H19 122.8 . . ? C19 C20 C15 114.7(2) . . ? C19 C20 H20 122.7 . . ? C15 C20 H20 122.7 . . ? 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 C13 C1 C2 C3 57.9(2) . . . . ? C6 C1 C2 C3 -58.1(2) . . . . ? Cl1 C1 C2 C3 179.59(15) . . . . ? C13 C1 C2 Cl2 -121.68(17) . . . . ? C6 C1 C2 Cl2 122.25(16) . . . . ? Cl1 C1 C2 Cl2 0.0(2) . . . . ? C1 C2 C3 C4 0.6(2) . . . . ? Cl2 C2 C3 C4 -179.81(15) . . . . ? C1 C2 C3 Cl3 179.25(15) . . . . ? Cl2 C2 C3 Cl3 -1.1(3) . . . . ? C2 C3 C4 C14 -58.4(2) . . . . ? Cl3 C3 C4 C14 122.88(16) . . . . ? C2 C3 C4 C5 58.2(2) . . . . ? Cl3 C3 C4 C5 -120.46(16) . . . . ? C2 C3 C4 Cl4 179.69(15) . . . . ? Cl3 C3 C4 Cl4 1.0(2) . . . . ? C3 C4 C5 C10 66.0(2) . . . . ? C14 C4 C5 C10 -176.27(16) . . . . ? Cl4 C4 C5 C10 -58.0(2) . . . . ? C3 C4 C5 C6 -57.7(2) . . . . ? C14 C4 C5 C6 60.0(2) . . . . ? Cl4 C4 C5 C6 178.31(13) . . . . ? C2 C1 C6 C7 -72.0(2) . . . . ? C13 C1 C6 C7 170.08(17) . . . . ? Cl1 C1 C6 C7 52.4(2) . . . . ? C2 C1 C6 C5 52.4(2) . . . . ? C13 C1 C6 C5 -65.49(19) . . . . ? Cl1 C1 C6 C5 176.80(13) . . . . ? C4 C5 C6 C1 3.6(2) . . . . ? C10 C5 C6 C1 -124.60(18) . . . . ? C4 C5 C6 C7 132.82(17) . . . . ? C10 C5 C6 C7 4.7(2) . . . . ? C1 C6 C7 C12 67.4(2) . . . . ? C5 C6 C7 C12 -56.6(2) . . . . ? C1 C6 C7 C8 -176.76(17) . . . . ? C5 C6 C7 C8 59.2(2) . . . . ? C12 C7 C8 C9 52.7(2) . . . . ? C6 C7 C8 C9 -64.6(2) . . . . ? C7 C8 C9 C10 3.6(2) . . . . ? C8 C9 C10 C11 -57.7(2) . . . . ? C8 C9 C10 C5 60.8(2) . . . . ? C4 C5 C10 C11 -74.1(2) . . . . ? C6 C5 C10 C11 49.6(2) . . . . ? C4 C5 C10 C9 170.67(17) . . . . ? C6 C5 C10 C9 -65.6(2) . . . . ? C9 C10 C11 C12 58.1(2) . . . . ? C5 C10 C11 C12 -56.3(3) . . . . ? C10 C11 C12 C7 1.3(3) . . . . ? C8 C7 C12 C11 -58.5(2) . . . . ? C6 C7 C12 C11 56.1(2) . . . . ? C2 C1 C13 C18 69.1(2) . . . . ? C6 C1 C13 C18 -172.43(16) . . . . ? Cl1 C1 C13 C18 -54.7(2) . . . . ? C2 C1 C13 C14 -55.4(2) . . . . ? C6 C1 C13 C14 63.0(2) . . . . ? Cl1 C1 C13 C14 -179.27(13) . . . . ? C3 C4 C14 C15 -69.5(2) . . . . ? C5 C4 C14 C15 173.19(16) . . . . ? Cl4 C4 C14 C15 54.9(2) . . . . ? C3 C4 C14 C13 54.7(2) . . . . ? C5 C4 C14 C13 -62.6(2) . . . . ? Cl4 C4 C14 C13 179.10(13) . . . . ? C1 C13 C14 C4 0.6(2) . . . . ? C18 C13 C14 C4 -128.53(17) . . . . ? C1 C13 C14 C15 129.70(17) . . . . ? C18 C13 C14 C15 0.5(2) . . . . ? C4 C14 C15 C20 71.1(2) . . . . ? C13 C14 C15 C20 -53.2(2) . . . . ? C4 C14 C15 C16 -173.42(17) . . . . ? C13 C14 C15 C16 62.3(2) . . . . ? C20 C15 C16 C17 54.7(2) . . . . ? C14 C15 C16 C17 -63.4(2) . . . . ? C15 C16 C17 C18 0.6(3) . . . . ? C16 C17 C18 C19 -55.6(2) . . . . ? C16 C17 C18 C13 62.6(2) . . . . ? C1 C13 C18 C19 -71.9(2) . . . . ? C14 C13 C18 C19 52.3(2) . . . . ? C1 C13 C18 C17 172.73(17) . . . . ? C14 C13 C18 C17 -63.1(2) . . . . ? C17 C18 C19 C20 58.5(2) . . . . ? C13 C18 C19 C20 -55.6(2) . . . . ? C18 C19 C20 C15 -0.1(3) . . . . ? C16 C15 C20 C19 -58.0(2) . . . . ? C14 C15 C20 C19 56.0(2) . . . . ? _audit_block_code C20H20Cl4_rv254_trauner _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C20 H20 Cl4' _chemical_formula_sum 'C20 H20 Cl4' _chemical_formula_weight 402.184 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 2 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.52931(16) _exptl_crystal_F_000 416 _database_code_depnum_ccdc_archive 'CCDC 949956'