# Electronic Supplementary Material (ESI) for CrystEngComm # 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_100K _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 H3 Br O2' _chemical_formula_sum 'C3 H3 Br O2' _chemical_formula_weight 150.96 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'C m c 21' _symmetry_space_group_name_Hall 'C 2c -2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 6.3090(6) _cell_length_b 10.7274(9) _cell_length_c 6.3907(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 432.52(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4150 _cell_measurement_theta_min 3.7467 _cell_measurement_theta_max 35.0864 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 9.342 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2444 _exptl_absorpt_correction_T_max 0.4552 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Incoatec microsource' _diffrn_radiation_monochromator 'Multilayer optics' _diffrn_measurement_device_type 'SMART CCD area detecotr' _diffrn_measurement_method 'omea scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11164 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 49.25 _reflns_number_total 2252 _reflns_number_gt 1770 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0400P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.020(15) _refine_ls_number_reflns 2252 _refine_ls_number_parameters 37 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0830 _refine_ls_wR_factor_gt 0.0792 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 Br1 Br 0.5000 0.595360(16) 0.45172(6) 0.01613(6) Uani 1 2 d S . . O1 O 0.5000 0.85747(19) 0.2249(3) 0.0183(3) Uani 1 2 d S . . O2 O 0.5000 0.69731(19) 0.9137(3) 0.0173(3) Uani 1 2 d S . . H2 H 0.5000 0.7323 1.0313 0.026 Uiso 1 2 calc SR . . C3 C 0.5000 0.7822(2) 0.7661(4) 0.0147(4) Uani 1 2 d S . . H3 H 0.5000 0.8671 0.8083 0.018 Uiso 1 2 calc SR . . C1 C 0.5000 0.8629(2) 0.4167(4) 0.0170(5) Uani 1 2 d S . . H1 H 0.5000 0.9436 0.4779 0.020 Uiso 1 2 calc SR . . C2 C 0.5000 0.7582(2) 0.5573(4) 0.0144(4) Uani 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 Br1 0.02177(10) 0.01100(7) 0.01561(9) -0.00200(12) 0.000 0.000 O1 0.0260(9) 0.0166(7) 0.0124(7) 0.0007(6) 0.000 0.000 O2 0.0238(8) 0.0172(6) 0.0109(9) 0.0019(5) 0.000 0.000 C3 0.0170(10) 0.0132(7) 0.0139(9) 0.0000(6) 0.000 0.000 C1 0.0227(10) 0.0126(7) 0.0156(13) 0.0005(6) 0.000 0.000 C2 0.0181(10) 0.0113(7) 0.0136(9) -0.0002(6) 0.000 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 Br1 C2 1.873(2) . ? O1 C1 1.227(3) . ? O2 C3 1.311(3) . ? O2 H2 0.8400 . ? C3 C2 1.358(3) . ? C3 H3 0.9500 . ? C1 C2 1.438(3) . ? C1 H1 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 C3 O2 H2 109.5 . . ? O2 C3 C2 125.1(2) . . ? O2 C3 H3 117.4 . . ? C2 C3 H3 117.4 . . ? O1 C1 C2 126.0(2) . . ? O1 C1 H1 117.0 . . ? C2 C1 H1 117.0 . . ? C3 C2 C1 117.8(2) . . ? C3 C2 Br1 122.04(17) . . ? C1 C2 Br1 120.20(17) . . ? 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 O2 C3 C2 C1 180.000(1) . . . . ? O2 C3 C2 Br1 0.000(2) . . . . ? O1 C1 C2 C3 180.000(1) . . . . ? O1 C1 C2 Br1 0.000(1) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 49.25 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.663 _refine_diff_density_min -1.079 _refine_diff_density_rms 0.162 _database_code_depnum_ccdc_archive 'CCDC 955205' ####################################################################### # # 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_291K _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 H3 Br O2' _chemical_formula_sum 'C3 H3 Br O2' _chemical_formula_weight 150.96 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'C m c 21' _symmetry_space_group_name_Hall 'C 2c -2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 6.503(13) _cell_length_b 10.85(2) _cell_length_c 6.429(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 453.6(16) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1494 _cell_measurement_theta_min 3.6532 _cell_measurement_theta_max 27.7889 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 8.907 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5360 _exptl_absorpt_correction_T_max 0.6170 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Incoatec microsource' _diffrn_radiation_monochromator 'multilayer optics' _diffrn_measurement_device_type 'SMART CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3146 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 30.43 _reflns_number_total 705 _reflns_number_gt 660 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0100P)^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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0105(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.017(17) _refine_ls_number_reflns 705 _refine_ls_number_parameters 47 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0212 _refine_ls_R_factor_gt 0.0190 _refine_ls_wR_factor_ref 0.0406 _refine_ls_wR_factor_gt 0.0398 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.5000 0.40193(2) 0.08676(8) 0.04299(13) Uani 1 2 d S . . O1 O 0.5000 0.1425(3) -0.1393(4) 0.0497(6) Uani 1 2 d S . . O2 O 0.5000 0.3029(3) 0.5472(4) 0.0459(7) Uani 1 2 d S . . H2 H 0.5000 0.270(4) 0.666(7) 0.015(10) Uiso 1 2 d S . . C1 C 0.5000 0.2177(3) 0.4000(4) 0.0342(7) Uani 1 2 d S . . H1 H 0.5000 0.138(5) 0.435(9) 0.060(14) Uiso 1 2 d S . . C2 C 0.5000 0.2406(3) 0.1919(5) 0.0335(6) Uani 1 2 d S . . C3 C 0.5000 0.1383(3) 0.0520(6) 0.0412(9) Uani 1 2 d S . . H3 H 0.5000 0.068(4) 0.121(11) 0.054(13) 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 Br1 0.0629(2) 0.03343(16) 0.03260(16) 0.0062(2) 0.000 0.000 O1 0.0737(17) 0.0497(15) 0.0256(13) -0.0065(12) 0.000 0.000 O2 0.0688(16) 0.0475(16) 0.0213(17) -0.0029(11) 0.000 0.000 C1 0.0437(17) 0.0361(17) 0.0228(15) -0.0003(13) 0.000 0.000 C2 0.0439(17) 0.0305(13) 0.0259(15) 0.0028(11) 0.000 0.000 C3 0.0579(18) 0.0394(15) 0.026(3) 0.0000(13) 0.000 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 Br1 C2 1.876(4) . ? O1 C3 1.231(5) . ? O2 C1 1.323(5) . ? O2 H2 0.84(4) . ? C1 C2 1.361(5) . ? C1 H1 0.90(6) . ? C2 C3 1.429(5) . ? C3 H3 0.88(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 O2 H2 110(3) . . ? O2 C1 C2 125.1(3) . . ? O2 C1 H1 120(4) . . ? C2 C1 H1 115(4) . . ? C1 C2 C3 118.5(3) . . ? C1 C2 Br1 121.6(2) . . ? C3 C2 Br1 119.9(3) . . ? O1 C3 C2 126.9(4) . . ? O1 C3 H3 122(4) . . ? C2 C3 H3 111(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 O2 C1 C2 C3 180.0 . . . . ? O2 C1 C2 Br1 0.0 . . . . ? C1 C2 C3 O1 180.0 . . . . ? Br1 C2 C3 O1 0.0 . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 30.43 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.204 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 955206'