# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_I_bh1 _database_code_depnum_ccdc_archive 'CCDC 893306' #TrackingRef '12794_web_deposit_cif_file_0_DmitryYufit_1343064849.Yufit_etal.cif' _audit_creation_date 2011-06-28 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; molecular complex of bromoform with cyclohexanone (1:1) ; _chemical_formula_moiety 'C H Br3, C6 H10 O' _chemical_formula_sum 'C7 H11 Br3 O' _chemical_formula_weight 350.89 _chemical_melting_point 224 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 8.4762(9) _cell_length_b 15.787(2) _cell_length_c 8.3158(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.210(10) _cell_angle_gamma 90.00 _cell_volume 1104.0(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1847 _cell_measurement_temperature 210 _cell_measurement_theta_max 24.11 _cell_measurement_theta_min 2.57 _exptl_absorpt_coefficient_mu 10.913 _exptl_absorpt_correction_T_max 0.1001 _exptl_absorpt_correction_T_min 0.0005 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2006/1 (Bruker,2006) was used for absorption correction. R(int) was 0.1173 before and 0.0289 after correction. The Ratio of minimum to maximum transmission is 0.004995004995. The \l/2 correction factor is 0.0015 ; _exptl_crystal_colour 'dull white colourless' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier white _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 2.111 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (10.00 s exposure) covering -0.300\ degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_unetI/netI 0.0456 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 8404 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_min 2.42 _diffrn_ambient_temperature 210 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.937 _diffrn_measured_fraction_theta_max 0.937 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 10.0 _diffrn_source_power 0.3 _diffrn_source_target Mo _diffrn_source_voltage 30.0 _diffrn_special_details ? _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1636 _reflns_number_total 2500 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.634 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.093 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 100 _refine_ls_number_reflns 2500 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0730 _refine_ls_R_factor_gt 0.0379 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0826 _refine_ls_wR_factor_ref 0.0923 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.50671(6) 0.39060(3) 0.59423(6) 0.05756(17) Uani 1 1 d . . . Br2 Br 0.12990(6) 0.39976(3) 0.57371(6) 0.05824(17) Uani 1 1 d . . . Br3 Br 0.29172(7) 0.28946(4) 0.32189(7) 0.0753(2) Uani 1 1 d . . . O1 O 0.1539(4) 0.5540(3) 0.2215(5) 0.0796(12) Uani 1 1 d . . . C1 C 0.1580(6) 0.5742(3) 0.0802(6) 0.0553(12) Uani 1 1 d . . . C1S C 0.3086(6) 0.3902(3) 0.4535(6) 0.0478(11) Uani 1 1 d . . . H1S H 0.3077 0.4393 0.3813 0.057 Uiso 1 1 calc R . . C2 C 0.2563(8) 0.5277(4) -0.0242(8) 0.0801(18) Uani 1 1 d . . . H2A H 0.1878 0.4942 -0.1020 0.096 Uiso 1 1 calc R . . H2B H 0.3261 0.4891 0.0419 0.096 Uiso 1 1 calc R . . C3 C 0.3554(8) 0.5865(5) -0.1140(8) 0.0842(19) Uani 1 1 d . . . H3A H 0.4389 0.6110 -0.0377 0.101 Uiso 1 1 calc R . . H3B H 0.4055 0.5541 -0.1928 0.101 Uiso 1 1 calc R . . C4 C 0.2586(7) 0.6565(4) -0.1997(6) 0.0747(17) Uani 1 1 d . . . H4A H 0.3280 0.6948 -0.2491 0.090 Uiso 1 1 calc R . . H4B H 0.1829 0.6328 -0.2850 0.090 Uiso 1 1 calc R . . C5 C 0.1725(8) 0.7038(4) -0.0838(8) 0.091(2) Uani 1 1 d . . . H5A H 0.1071 0.7470 -0.1422 0.109 Uiso 1 1 calc R . . H5B H 0.2492 0.7321 -0.0054 0.109 Uiso 1 1 calc R . . C6 C 0.0676(7) 0.6471(4) 0.0057(8) 0.0775(17) Uani 1 1 d . . . H6A H 0.0250 0.6796 0.0893 0.093 Uiso 1 1 calc R . . H6B H -0.0211 0.6268 -0.0695 0.093 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 0.0541(3) 0.0548(3) 0.0616(3) 0.0012(2) -0.0014(3) -0.0015(2) Br2 0.0559(3) 0.0619(3) 0.0589(3) -0.0003(2) 0.0148(3) 0.0018(2) Br3 0.0795(4) 0.0758(4) 0.0720(4) -0.0311(3) 0.0147(3) -0.0107(3) O1 0.068(3) 0.109(3) 0.061(2) 0.014(2) 0.009(2) -0.004(2) C1 0.044(3) 0.066(3) 0.055(3) 0.001(3) 0.004(2) -0.003(2) C1S 0.047(3) 0.048(3) 0.048(3) 0.002(2) 0.004(2) -0.004(2) C2 0.088(4) 0.074(4) 0.083(4) -0.003(3) 0.029(4) 0.024(3) C3 0.070(4) 0.106(5) 0.083(4) -0.008(4) 0.033(3) 0.019(4) C4 0.075(4) 0.097(5) 0.054(3) 0.012(3) 0.015(3) -0.001(3) C5 0.110(5) 0.060(4) 0.110(5) 0.016(3) 0.046(4) 0.013(3) C6 0.066(3) 0.085(4) 0.088(4) 0.011(3) 0.034(3) 0.022(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 Br1 C1S 1.922(5) . ? Br2 C1S 1.923(5) . ? Br3 C1S 1.926(5) . ? O1 C1 1.222(6) . ? C1 C2 1.473(7) . ? C1 C6 1.475(8) . ? C1S H1S 0.9800 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2 C3 1.511(8) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 C4 1.501(9) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 C5 1.482(8) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 C6 1.521(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? 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 O1 C1 C2 121.6(5) . . ? O1 C1 C6 122.1(5) . . ? C2 C1 C6 116.3(5) . . ? Br1 C1S Br2 111.6(2) . . ? Br1 C1S Br3 110.2(2) . . ? Br1 C1S H1S 108.1 . . ? Br2 C1S Br3 110.7(2) . . ? Br2 C1S H1S 108.1 . . ? Br3 C1S H1S 108.1 . . ? C1 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C1 C2 C3 112.1(5) . . ? H2A C2 H2B 107.9 . . ? C3 C2 H2A 109.2 . . ? C3 C2 H2B 109.2 . . ? C2 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C4 C3 C2 112.5(5) . . ? C4 C3 H3A 109.1 . . ? C4 C3 H3B 109.1 . . ? C3 C4 H4A 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C5 C4 C3 110.3(5) . . ? C5 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C4 C5 H5A 109.0 . . ? C4 C5 H5B 109.0 . . ? C4 C5 C6 112.8(5) . . ? H5A C5 H5B 107.8 . . ? C6 C5 H5A 109.0 . . ? C6 C5 H5B 109.0 . . ? C1 C6 C5 111.1(5) . . ? C1 C6 H6A 109.4 . . ? C1 C6 H6B 109.4 . . ? C5 C6 H6A 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? 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 C1S H1S O1 0.98 2.51 3.391(6) 149.1 . data_II_bbs _database_code_depnum_ccdc_archive 'CCDC 893307' #TrackingRef '12794_web_deposit_cif_file_0_DmitryYufit_1343064849.Yufit_etal.cif' _audit_creation_date 2012-07-16 _audit_creation_method ; Olex2 1.2-beta (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; molecular complex of bromoform with dimethylsulfoxide (1:1) ; _chemical_formula_moiety 'C2 H6 O S, C H Br3' _chemical_formula_sum 'C3 H7 Br3 O S' _chemical_formula_weight 330.88 _chemical_absolute_configuration ad _chemical_melting_point 236-238 _chemical_oxdiff_formula 'C3 H7 Br3 S1 O1' _chemical_oxdiff_usercomment 'Grown in situ at 228K' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_H-M_alt 'C 1 c 1' _space_group_name_Hall 'C -2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 'x, -y, z+1/2' 3 'x+1/2, y+1/2, z' 4 'x+1/2, -y+1/2, z+1/2' _cell_length_a 7.9562(8) _cell_length_b 9.6768(9) _cell_length_c 12.0633(17) _cell_angle_alpha 90.00 _cell_angle_beta 94.923(11) _cell_angle_gamma 90.00 _cell_volume 925.33(18) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2036 _cell_measurement_temperature 225 _cell_measurement_theta_max 33.0749 _cell_measurement_theta_min 3.3155 _exptl_absorpt_coefficient_mu 13.229 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.14125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'dull light white' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary white _exptl_crystal_density_diffrn 2.375 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_F_000 616 _exptl_crystal_recrystallization_method 'Grown in situ @228K' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.1023 _diffrn_reflns_av_unetI/netI 0.0979 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 7041 _diffrn_reflns_theta_full 29.47 _diffrn_reflns_theta_max 29.47 _diffrn_reflns_theta_min 3.32 _diffrn_ambient_temperature 225 _diffrn_detector CCD _diffrn_detector_area_resol_mean 16.1511 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -63.00 32.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.1216 77.0000 120.0000 190 #__ type_ start__ end____ width___ exp.time_ 2 omega -101.00 35.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.1216 -19.0000 -30.0000 272 #__ type_ start__ end____ width___ exp.time_ 3 omega 71.00 103.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - 31.7466 179.0000 120.0000 64 #__ type_ start__ end____ width___ exp.time_ 4 omega -102.00 -7.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.1216 -57.0000 -90.0000 190 #__ type_ start__ end____ width___ exp.time_ 5 omega -105.00 0.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.1216 -38.0000 150.0000 210 #__ type_ start__ end____ width___ exp.time_ 6 omega -55.00 39.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.1216 57.0000 0.0000 188 #__ type_ start__ end____ width___ exp.time_ 7 omega 56.00 112.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - 31.7466 179.0000 -60.0000 112 #__ type_ start__ end____ width___ exp.time_ 8 omega -1.00 104.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - 31.7466 77.0000 90.0000 210 #__ type_ start__ end____ width___ exp.time_ 9 omega 56.00 112.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - 31.7466 179.0000 0.0000 112 #__ type_ start__ end____ width___ exp.time_ 10 omega -111.00 -81.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.1216 -179.0000 -30.0000 60 ; _diffrn_measurement_device '3-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0824365000 _diffrn_orient_matrix_UB_12 0.0219456000 _diffrn_orient_matrix_UB_13 0.0195218000 _diffrn_orient_matrix_UB_21 -0.0312668000 _diffrn_orient_matrix_UB_22 0.0672882000 _diffrn_orient_matrix_UB_23 0.0089208000 _diffrn_orient_matrix_UB_31 -0.0160243000 _diffrn_orient_matrix_UB_32 -0.0186913000 _diffrn_orient_matrix_UB_33 0.0549584000 _diffrn_radiation_collimation monochromator _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_xray_symbol Mo _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_type 'sealed tube' _diffrn_source_voltage n/a _diffrn_special_details ? _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1915 _reflns_number_total 2557 _reflns_odcompleteness_completeness 99.88 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 31.44 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 1.841 _refine_diff_density_min -2.000 _refine_diff_density_rms 0.267 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(4) _refine_ls_extinction_coef 0.0049(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 76 _refine_ls_number_reflns 2557 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1038 _refine_ls_R_factor_gt 0.0833 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1357P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2103 _refine_ls_wR_factor_ref 0.2358 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 S1 S 0.8588(4) 0.5192(4) 0.8467(3) 0.0411(8) Uani 1 1 d . . . O1 O 0.6850(12) 0.5758(13) 0.8576(9) 0.052(3) Uani 1 1 d . . . C1 C 0.872(2) 0.3574(16) 0.9153(15) 0.048(4) Uani 1 1 d . . . H1A H 0.7907 0.2951 0.8794 0.073 Uiso 1 1 calc R . . H1B H 0.8496 0.3693 0.9916 0.073 Uiso 1 1 calc R . . H1C H 0.9833 0.3199 0.9120 0.073 Uiso 1 1 calc R . . C2 C 0.997(2) 0.6099(16) 0.9443(19) 0.065(5) Uani 1 1 d . . . H2A H 0.9599 0.5989 1.0175 0.097 Uiso 1 1 calc R . . H2B H 0.9969 0.7062 0.9253 0.097 Uiso 1 1 calc R . . H2C H 1.1092 0.5737 0.9431 0.097 Uiso 1 1 calc R . . Br1 Br 0.50479(14) 0.48018(14) 0.55461(12) 0.0433(4) Uani 1 1 d . . . Br2 Br 0.27358(18) 0.35768(18) 0.73364(15) 0.0547(5) Uani 1 1 d . . . Br3 Br 0.22470(18) 0.66779(16) 0.65021(14) 0.0512(5) Uani 1 1 d . . . C1S C 0.3863(17) 0.5177(12) 0.6825(12) 0.040(3) Uani 1 1 d . . . H1S H 0.4687 0.5484 0.7425 0.048 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 S1 0.0255(15) 0.049(2) 0.0474(18) 0.0060(14) -0.0060(12) -0.0027(13) O1 0.024(4) 0.070(7) 0.059(6) 0.013(5) -0.009(4) 0.000(5) C1 0.040(8) 0.035(7) 0.070(10) -0.006(6) 0.004(7) -0.004(6) C2 0.027(7) 0.035(7) 0.127(16) -0.003(9) -0.025(8) 0.000(6) Br1 0.0320(6) 0.0366(7) 0.0604(9) 0.0017(5) -0.0020(5) 0.0061(5) Br2 0.0404(8) 0.0488(9) 0.0744(11) 0.0148(7) 0.0012(7) 0.0034(6) Br3 0.0416(8) 0.0425(7) 0.0668(9) -0.0041(6) -0.0102(6) 0.0182(6) C1S 0.032(6) 0.025(6) 0.060(8) -0.007(5) -0.009(6) 0.013(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.504(11) . ? S1 C1 1.770(16) . ? S1 C2 1.774(17) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? Br1 C1S 1.910(14) . ? Br2 C1S 1.918(14) . ? Br3 C1S 1.957(12) . ? C1S H1S 0.9800 . ? 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 O1 S1 C1 107.5(7) . . ? O1 S1 C2 106.5(8) . . ? C2 S1 C1 96.8(8) . . ? S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? S1 C2 H2A 109.5 . . ? S1 C2 H2B 109.5 . . ? S1 C2 H2C 109.5 . . ? H2A C2 H2B 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? Br1 C1S Br2 112.5(6) . . ? Br1 C1S Br3 110.0(7) . . ? Br1 C1S H1S 108.0 . . ? Br2 C1S Br3 110.2(7) . . ? Br2 C1S H1S 108.0 . . ? Br3 C1S H1S 108.0 . . ? data_III_160K_bfdo _database_code_depnum_ccdc_archive 'CCDC 893308' #TrackingRef '12794_web_deposit_cif_file_0_DmitryYufit_1343064849.Yufit_etal.cif' _audit_creation_date 2011-10-06 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.09.28 svn.r2007, GUI svn.r3868) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '0.5(C10 H18 Br6 O4)' _chemical_formula_sum 'C5 H9 Br3 O2' _chemical_formula_weight 340.85 _chemical_melting_point 255-257 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 11 _space_group_name_H-M_alt 'P 1 21/m 1' _space_group_name_Hall '-P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' 3 '-x, -y, -z' 4 'x, -y-1/2, z' _cell_length_a 4.1771(3) _cell_length_b 19.2999(16) _cell_length_c 6.0082(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.732(10) _cell_angle_gamma 90.00 _cell_volume 463.86(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used ? _cell_measurement_temperature 160 _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 12.990 _exptl_absorpt_correction_T_max 0.1088 _exptl_absorpt_correction_T_min 0.0485 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2006/1 (Bruker,2006) was used for absorption correction. R(int) was 0.0284 before and 0.0156 after correction. The Ratio of minimum to maximum transmission is 0.4458. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'dull whitish colourless' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier whitish _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 2.440 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (10 s exposure) covering -0.300\% degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_unetI/netI 0.0174 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 3058 _diffrn_reflns_theta_full 29.49 _diffrn_reflns_theta_max 29.49 _diffrn_reflns_theta_min 2.11 _diffrn_ambient_temperature 160 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.789 _diffrn_measured_fraction_theta_max 0.789 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 10.0 _diffrn_source_power 0.3 _diffrn_source_target Mo _diffrn_source_voltage 30.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 974 _reflns_number_total 1048 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.525 _refine_diff_density_min -0.506 _refine_diff_density_rms 0.085 _refine_ls_extinction_coef 0.0220(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 66 _refine_ls_number_reflns 1048 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0208 _refine_ls_R_factor_gt 0.0182 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0250P)^2^+0.2000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.0457 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0277(5) 0.45614(8) 0.1834(3) 0.0262(4) Uani 1 1 d . . . C1 C -0.0133(7) 0.42885(12) -0.0350(5) 0.0287(6) Uani 1 1 d . . . C2 C 0.1543(7) 0.51989(12) 0.2279(4) 0.0270(5) Uani 1 1 d . . . H1A H -0.148(8) 0.3872(16) -0.062(5) 0.033(8) Uiso 1 1 d . . . H1B H 0.212(6) 0.4186(15) -0.026(4) 0.017(6) Uiso 1 1 d . . . H2A H 0.403(7) 0.5116(15) 0.253(5) 0.028(7) Uiso 1 1 d . . . H2B H 0.141(8) 0.5375(17) 0.365(6) 0.043(9) Uiso 1 1 d . . . Br1 Br 0.25540(6) 0.332385(11) 0.46533(4) 0.02633(11) Uani 1 1 d . . . Br2 Br 0.42978(10) 0.2500 0.94200(6) 0.02931(12) Uani 1 2 d S . . C1S C 0.4560(8) 0.2500 0.6269(6) 0.0199(5) Uiso 1 2 d S . . H1S H 0.661(11) 0.2500 0.646(7) 0.027(10) Uiso 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0388(10) 0.0175(7) 0.0279(9) 0.0051(6) 0.0185(9) 0.0002(6) C1 0.0429(15) 0.0158(10) 0.0335(13) 0.0013(9) 0.0207(13) 0.0008(9) C2 0.0364(15) 0.0205(10) 0.0272(12) 0.0003(9) 0.0138(13) -0.0015(9) Br1 0.0398(2) 0.01616(12) 0.02645(17) 0.00280(7) 0.01503(15) 0.00145(8) Br2 0.0463(3) 0.02330(16) 0.0221(2) 0.000 0.0157(2) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.431(3) . ? O1 C2 1.431(3) . ? O1 H2B 2.89(4) 3_566 ? O1 Br1 2.9697(16) . ? C1 C2 1.508(3) 3_565 ? C1 H1A 0.97(3) . ? C1 H1B 0.95(3) . ? C2 C1 1.508(3) 3_565 ? C2 H2A 1.02(3) . ? C2 H2B 0.91(4) . ? Br1 C1S 1.925(2) . ? Br2 C1S 1.928(3) . ? C1S Br1 1.925(2) 4_565 ? C1S H1S 0.83(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H2B 159.8(7) . 3_566 ? C1 O1 Br1 96.43(12) . . ? C2 O1 C1 109.10(16) . . ? C2 O1 H2B 90.6(6) . 3_566 ? C2 O1 Br1 118.83(15) . . ? H2B O1 Br1 69.2(6) 3_566 . ? O1 C1 C2 110.67(18) . 3_565 ? O1 C1 H1A 106.6(19) . . ? O1 C1 H1B 109.1(16) . . ? C2 C1 H1A 109.5(19) 3_565 . ? C2 C1 H1B 110.0(16) 3_565 . ? H1A C1 H1B 111(3) . . ? O1 C2 C1 110.6(2) . 3_565 ? O1 C2 H2A 110.9(17) . . ? O1 C2 H2B 109(2) . . ? C1 C2 H2A 112.0(17) 3_565 . ? C1 C2 H2B 110(2) 3_565 . ? H2A C2 H2B 104(3) . . ? C1S Br1 O1 175.00(9) . . ? Br1 C1S Br1 111.42(18) . 4_565 ? Br1 C1S Br2 110.84(10) 4_565 . ? Br1 C1S Br2 110.84(10) . . ? Br1 C1S H1S 110.6(14) 4_565 . ? Br1 C1S H1S 110.6(14) . . ? Br2 C1S H1S 102(3) . . ? data_III_200K_bfdo _database_code_depnum_ccdc_archive 'CCDC 893309' #TrackingRef '12794_web_deposit_cif_file_0_DmitryYufit_1343064849.Yufit_etal.cif' _audit_creation_date 2011-10-06 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.09.28 svn.r2007, GUI svn.r3868) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '0.5(C10 H18 Br6 O4)' _chemical_formula_sum 'C5 H9 Br3 O2' _chemical_formula_weight 340.85 _chemical_melting_point ? 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 11 _space_group_name_H-M_alt 'P 1 21/m 1' _space_group_name_Hall '-P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' 3 '-x, -y, -z' 4 'x, -y-1/2, z' _cell_length_a 4.2028(4) _cell_length_b 19.3569(18) _cell_length_c 6.0247(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.761(10) _cell_angle_gamma 90.00 _cell_volume 469.31(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1246 _cell_measurement_temperature 200 _cell_measurement_theta_max 31.00 _cell_measurement_theta_min 3.53 _exptl_absorpt_coefficient_mu 12.839 _exptl_absorpt_correction_T_max 0.1045 _exptl_absorpt_correction_T_min 0.0514 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2006/1 (Bruker,2006) was used for absorption correction. R(int) was 0.0299 before and 0.0188 after correction. The Ratio of minimum to maximum transmission is 0.4919. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'dull light colourless' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 2.412 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (10 s exposure) covering -0.300\% degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_unetI/netI 0.0165 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 4033 _diffrn_reflns_theta_full 29.46 _diffrn_reflns_theta_max 29.46 _diffrn_reflns_theta_min 2.10 _diffrn_ambient_temperature 200 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.787 _diffrn_measured_fraction_theta_max 0.787 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 985 _reflns_number_total 1055 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.466 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.083 _refine_ls_extinction_coef 0.0212(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 66 _refine_ls_number_reflns 1055 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0234 _refine_ls_R_factor_gt 0.0212 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0250P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.0516 _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. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0290(5) 0.45632(9) 0.1821(4) 0.0334(4) Uani 1 1 d . . . C1 C -0.0162(9) 0.42935(13) -0.0354(6) 0.0360(7) Uani 1 1 d . . . C2 C 0.1556(8) 0.51948(14) 0.2279(5) 0.0345(7) Uani 1 1 d . . . H1A H -0.152(10) 0.388(2) -0.065(7) 0.050(10) Uiso 1 1 d . . . H1B H 0.205(8) 0.4201(18) -0.029(6) 0.032(8) Uiso 1 1 d . . . H2A H 0.401(9) 0.5103(18) 0.253(6) 0.039(9) Uiso 1 1 d . . . H2B H 0.132(10) 0.5388(19) 0.371(7) 0.053(11) Uiso 1 1 d . . . Br1 Br 0.25383(8) 0.332092(12) 0.46431(5) 0.03398(13) Uani 1 1 d . . . Br2 Br 0.42776(12) 0.2500 0.93925(7) 0.03782(15) Uani 1 2 d S . . C1S C 0.4545(10) 0.2500 0.6257(7) 0.0262(7) Uiso 1 2 d S . . H1S H 0.664(11) 0.2500 0.648(8) 0.025(10) Uiso 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0478(12) 0.0242(8) 0.0343(10) 0.0066(7) 0.0216(10) 0.0011(8) C1 0.0532(19) 0.0192(11) 0.0410(17) 0.0032(10) 0.0223(17) 0.0016(11) C2 0.0469(19) 0.0270(12) 0.0329(16) 0.0005(10) 0.0166(16) -0.0018(11) Br1 0.0514(2) 0.02146(13) 0.0325(2) 0.00365(9) 0.01757(18) 0.00185(10) Br2 0.0599(3) 0.03060(19) 0.0268(2) 0.000 0.0185(2) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.426(3) . ? O1 C2 1.431(3) . ? O1 H2B 2.85(4) 3_566 ? O1 Br1 2.9868(19) . ? C1 C2 1.509(4) 3_565 ? C1 H1A 0.97(4) . ? C1 H1B 0.94(3) . ? C2 C1 1.509(4) 3_565 ? C2 H2A 1.02(4) . ? C2 H2B 0.97(4) . ? Br1 C1S 1.926(2) . ? Br2 C1S 1.925(4) . ? C1S Br1 1.926(2) 4_565 ? C1S H1S 0.85(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C2 109.16(19) . . ? C1 O1 H2B 159.5(8) . 3_566 ? C1 O1 Br1 96.55(14) . . ? C2 O1 H2B 90.6(8) . 3_566 ? C2 O1 Br1 118.25(17) . . ? H2B O1 Br1 68.5(8) 3_566 . ? O1 C1 C2 110.9(2) . 3_565 ? O1 C1 H1A 107(2) . . ? O1 C1 H1B 109(2) . . ? C2 C1 H1A 109(2) 3_565 . ? C2 C1 H1B 108(2) 3_565 . ? H1A C1 H1B 112(3) . . ? O1 C2 C1 110.1(3) . 3_565 ? O1 C2 H2A 111(2) . . ? O1 C2 H2B 108(2) . . ? C1 C2 H2A 113(2) 3_565 . ? C1 C2 H2B 108(2) 3_565 . ? H2A C2 H2B 107(3) . . ? C1S Br1 O1 174.98(11) . . ? Br1 C1S Br1 111.2(2) . 4_565 ? Br1 C1S H1S 111.2(14) . . ? Br1 C1S H1S 111.2(14) 4_565 . ? Br2 C1S Br1 110.76(12) . . ? Br2 C1S Br1 110.76(12) . 4_565 ? Br2 C1S H1S 101(3) . . ? data_III_240K_bfdo _database_code_depnum_ccdc_archive 'CCDC 893310' #TrackingRef '12794_web_deposit_cif_file_0_DmitryYufit_1343064849.Yufit_etal.cif' _audit_creation_date 2011-10-06 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.09.28 svn.r2007, GUI svn.r3868) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '0.5(C10 H18 Br6 O4)' _chemical_formula_sum 'C5 H9 Br3 O2' _chemical_formula_weight 340.85 _chemical_melting_point ? 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 11 _space_group_name_H-M_alt 'P 1 21/m 1' _space_group_name_Hall '-P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' 3 '-x, -y, -z' 4 'x, -y-1/2, z' _cell_length_a 4.2311(5) _cell_length_b 19.421(2) _cell_length_c 6.0413(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.760(10) _cell_angle_gamma 90.00 _cell_volume 475.33(9) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1059 _cell_measurement_temperature 240 _cell_measurement_theta_max 30.50 _cell_measurement_theta_min 3.52 _exptl_absorpt_coefficient_mu 12.677 _exptl_absorpt_correction_T_max 0.1053 _exptl_absorpt_correction_T_min 0.0485 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2006/1 (Bruker,2006) was used for absorption correction. R(int) was 0.0314 before and 0.0205 after correction. The Ratio of minimum to maximum transmission is 0.4606. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'dull light colourless' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 2.381 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_F_000 320 _exptl_crystal_recrystallization_method 'in situ' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (10 s exposure) covering -0.300\% degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_unetI/netI 0.0200 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 3946 _diffrn_reflns_theta_full 29.50 _diffrn_reflns_theta_max 29.50 _diffrn_reflns_theta_min 2.10 _diffrn_ambient_temperature 240 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.788 _diffrn_measured_fraction_theta_max 0.788 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 968 _reflns_number_total 1075 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.662 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.100 _refine_ls_extinction_coef 0.0216(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 66 _refine_ls_number_reflns 1075 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0244 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.0614 _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. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0298(6) 0.45665(10) 0.1813(4) 0.0416(5) Uani 1 1 d . . . C1 C -0.0190(11) 0.42977(15) -0.0354(7) 0.0446(8) Uani 1 1 d . . . C2 C 0.1549(10) 0.51909(17) 0.2269(6) 0.0437(8) Uani 1 1 d . . . H1A H -0.160(10) 0.390(2) -0.067(7) 0.047(10) Uiso 1 1 d . . . H1B H 0.195(10) 0.420(2) -0.029(7) 0.050(11) Uiso 1 1 d . . . H2A H 0.401(10) 0.512(2) 0.242(7) 0.046(10) Uiso 1 1 d . . . H2B H 0.144(11) 0.536(2) 0.376(9) 0.065(13) Uiso 1 1 d . . . Br1 Br 0.25193(9) 0.331769(14) 0.46312(6) 0.04281(16) Uani 1 1 d . . . Br2 Br 0.42544(15) 0.2500 0.93623(8) 0.04765(18) Uani 1 2 d S . . C1S C 0.4505(12) 0.2500 0.6239(8) 0.0330(8) Uiso 1 2 d S . . H1S H 0.658(12) 0.2500 0.639(8) 0.031(11) Uiso 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0587(15) 0.0310(10) 0.0424(12) 0.0090(8) 0.0261(12) 0.0007(9) C1 0.066(2) 0.0251(13) 0.049(2) 0.0035(12) 0.026(2) 0.0021(14) C2 0.058(2) 0.0367(14) 0.0394(19) 0.0014(13) 0.018(2) -0.0011(14) Br1 0.0637(3) 0.02821(16) 0.0398(2) 0.00471(11) 0.0201(2) 0.00233(12) Br2 0.0744(4) 0.0402(2) 0.0317(3) 0.000 0.0208(3) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.423(4) . ? O1 C2 1.426(4) . ? O1 H2B 2.85(5) 3_566 ? O1 Br1 3.005(2) . ? C1 C2 1.507(5) 3_565 ? C1 H1A 0.97(4) . ? C1 H1B 0.92(4) . ? C2 C1 1.507(5) 3_565 ? C2 H2A 1.03(4) . ? C2 H2B 0.98(5) . ? Br1 C1S 1.924(3) . ? Br2 C1S 1.920(4) . ? C1S Br1 1.924(3) 4_565 ? C1S H1S 0.85(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C2 109.2(2) . . ? C1 O1 H2B 160.0(9) . 3_566 ? C1 O1 Br1 96.46(16) . . ? C2 O1 H2B 90.4(9) . 3_566 ? C2 O1 Br1 118.1(2) . . ? H2B O1 Br1 69.9(9) 3_566 . ? O1 C1 C2 111.0(3) . 3_565 ? O1 C1 H1A 107(2) . . ? O1 C1 H1B 109(3) . . ? C2 C1 H1A 108(2) 3_565 . ? C2 C1 H1B 109(3) 3_565 . ? H1A C1 H1B 113(4) . . ? O1 C2 C1 110.2(3) . 3_565 ? O1 C2 H2A 112(2) . . ? O1 C2 H2B 107(3) . . ? C1 C2 H2A 108(2) 3_565 . ? C1 C2 H2B 112(3) 3_565 . ? H2A C2 H2B 106(4) . . ? C1S Br1 O1 175.15(13) . . ? Br1 C1S Br1 111.3(2) . 4_565 ? Br1 C1S H1S 109.8(16) . . ? Br1 C1S H1S 109.8(16) 4_565 . ? Br2 C1S Br1 110.87(14) . . ? Br2 C1S Br1 110.87(14) . 4_565 ? Br2 C1S H1S 104(3) . . ?