#------------------------------------------------------------------------------ #$Date: 2020-05-08 08:53:02 +0100 (Fri, 08 May 2020) $ #$Revision: 251903 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/01/3500102.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_3500102 loop_ _publ_author_name 'Thierry Maris' _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _journal_name_full 'Personal communication to COD' _journal_year 2020 _chemical_formula_moiety 'C9 H11 Br O3' _chemical_formula_sum 'C9 H11 Br O3' _chemical_formula_weight 247.09 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-09-06 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _cell_angle_alpha 90 _cell_angle_beta 98.309(6) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 30.333(3) _cell_length_b 4.6431(5) _cell_length_c 14.0351(14) _cell_measurement_reflns_used 8333 _cell_measurement_temperature 100 _cell_measurement_theta_max 60.849 _cell_measurement_theta_min 2.562 _cell_volume 1955.9(3) _computing_cell_refinement ; SAINT (2013) V8.35A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.' ; _computing_data_collection ; APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; SAINT (2013) V8.35A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.' ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XT (Sheldrick, 2015)' _diffrn_ambient_temperature 100 _diffrn_detector 'CMOS Area detector' _diffrn_detector_area_resol_mean 10.24 _diffrn_detector_type 'Bruker Photon 100 CMOS Detector' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device 'k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker Venture Metaljet' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Helios MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_unetI/netI 0.0373 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 10969 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 60.817 _diffrn_reflns_theta_min 2.561 _diffrn_source 'Metal Jet' _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _exptl_absorpt_coefficient_mu 3.658 _exptl_absorpt_correction_T_max 0.7519 _exptl_absorpt_correction_T_min 0.5311 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1335 before and 0.0751 after correction. The Ratio of minimum to maximum transmission is 0.7063. The \l/2 correction factor is 0.00150.' ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.678 _exptl_crystal_description Needle _exptl_crystal_F_000 992 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector, a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode. ; _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. ; _refine_diff_density_max 1.069 _refine_diff_density_min -0.547 _refine_diff_density_rms 0.110 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 121 _refine_ls_number_reflns 2229 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.073 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0398 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0415P)^2^+10.0319P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1007 _refine_ls_wR_factor_ref 0.1040 _refine_special_details ; _shelx_SHELXL_version_number 2018/3 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C2(H2), C6(H6) 2.b Idealised Me refined as rotating group: C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C) ; _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2014 _reflns_number_total 2229 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 123me5br.cif _cod_data_source_block 123me5br _cod_original_cell_volume 1955.9(4) _cod_database_code 3500102 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' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.52508(2) 0.44887(9) 0.37330(2) 0.03117(14) Uani 1 1 d . . . . . O1 O 0.69570(7) 0.6574(5) 0.48518(14) 0.0240(4) Uani 1 1 d . . . . . O2 O 0.69531(7) 0.3959(5) 0.65470(14) 0.0213(4) Uani 1 1 d . . . . . O3 O 0.62345(7) 0.1106(5) 0.69436(15) 0.0264(5) Uani 1 1 d . . . . . C1 C 0.57935(10) 0.4207(7) 0.4602(2) 0.0235(6) Uani 1 1 d . . . . . C2 C 0.61668(10) 0.5598(7) 0.4363(2) 0.0225(6) Uani 1 1 d . . . . . H2 H 0.615434 0.664097 0.377716 0.027 Uiso 1 1 calc R . . . . C3 C 0.65620(10) 0.5419(6) 0.5009(2) 0.0211(6) Uani 1 1 d . . . . . C4 C 0.65714(10) 0.3939(6) 0.58816(19) 0.0204(6) Uani 1 1 d . . . . . C5 C 0.61889(10) 0.2510(7) 0.60818(19) 0.0224(6) Uani 1 1 d . . . . . C6 C 0.57938(10) 0.2618(7) 0.5435(2) 0.0238(6) Uani 1 1 d . . . . . H6 H 0.553406 0.163421 0.556256 0.029 Uiso 1 1 calc R . . . . C7 C 0.69578(11) 0.8256(8) 0.3993(2) 0.0266(6) Uani 1 1 d . . . . . H7A H 0.685264 0.706930 0.342785 0.040 Uiso 1 1 calc GR . . . . H7B H 0.726116 0.892609 0.395491 0.040 Uiso 1 1 calc GR . . . . H7C H 0.676018 0.991933 0.400895 0.040 Uiso 1 1 calc GR . . . . C8 C 0.72181(10) 0.1387(7) 0.6522(2) 0.0250(6) Uani 1 1 d . . . . . H8A H 0.731433 0.120520 0.588789 0.038 Uiso 1 1 calc GR . . . . H8B H 0.703977 -0.029793 0.664362 0.038 Uiso 1 1 calc GR . . . . H8C H 0.748016 0.150743 0.701875 0.038 Uiso 1 1 calc GR . . . . C9 C 0.58671(11) -0.0634(7) 0.7135(2) 0.0291(7) Uani 1 1 d . . . . . H9A H 0.579539 -0.204692 0.661741 0.044 Uiso 1 1 calc GR . . . . H9B H 0.560738 0.059643 0.717005 0.044 Uiso 1 1 calc GR . . . . H9C H 0.594722 -0.164094 0.774958 0.044 Uiso 1 1 calc GR . . . . 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(2) 0.0490(3) 0.01954(18) -0.00332(14) -0.00186(12) 0.00562(14) O1 0.0265(10) 0.0281(11) 0.0165(9) 0.0033(8) 0.0003(8) -0.0029(9) O2 0.0249(10) 0.0217(11) 0.0158(9) -0.0014(8) -0.0021(8) 0.0004(8) O3 0.0306(11) 0.0313(12) 0.0165(9) 0.0046(9) 0.0004(8) -0.0068(9) C1 0.0238(14) 0.0295(16) 0.0155(12) -0.0059(11) -0.0027(10) 0.0045(12) C2 0.0260(14) 0.0267(16) 0.0147(12) -0.0007(11) 0.0022(10) 0.0042(11) C3 0.0244(14) 0.0229(15) 0.0159(13) -0.0039(11) 0.0025(10) 0.0007(11) C4 0.0245(14) 0.0210(14) 0.0145(12) -0.0026(10) -0.0008(10) 0.0011(11) C5 0.0304(15) 0.0234(15) 0.0134(12) -0.0014(11) 0.0030(10) 0.0001(12) C6 0.0253(14) 0.0270(16) 0.0194(13) -0.0045(12) 0.0042(11) -0.0001(12) C7 0.0325(15) 0.0308(17) 0.0163(13) 0.0040(12) 0.0028(11) -0.0010(13) C8 0.0268(14) 0.0249(15) 0.0217(13) -0.0005(12) -0.0023(11) 0.0027(12) C9 0.0327(17) 0.0297(17) 0.0255(15) 0.0025(13) 0.0060(13) -0.0081(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0390 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C3 O1 C7 117.3(2) . . C4 O2 C8 113.2(2) . . C5 O3 C9 117.0(2) . . C2 C1 Br1 118.2(2) . . C6 C1 Br1 118.2(2) . . C6 C1 C2 123.6(3) . . C1 C2 H2 121.0 . . C1 C2 C3 118.0(3) . . C3 C2 H2 121.0 . . O1 C3 C2 124.4(3) . . O1 C3 C4 115.4(3) . . C2 C3 C4 120.2(3) . . O2 C4 C3 119.8(3) . . O2 C4 C5 120.4(3) . . C5 C4 C3 119.7(3) . . O3 C5 C4 115.1(3) . . O3 C5 C6 124.2(3) . . C6 C5 C4 120.7(3) . . C1 C6 C5 117.7(3) . . C1 C6 H6 121.1 . . C5 C6 H6 121.1 . . O1 C7 H7A 109.5 . . O1 C7 H7B 109.5 . . O1 C7 H7C 109.5 . . H7A C7 H7B 109.5 . . H7A C7 H7C 109.5 . . H7B C7 H7C 109.5 . . O2 C8 H8A 109.5 . . O2 C8 H8B 109.5 . . O2 C8 H8C 109.5 . . H8A C8 H8B 109.5 . . H8A C8 H8C 109.5 . . H8B C8 H8C 109.5 . . O3 C9 H9A 109.5 . . O3 C9 H9B 109.5 . . O3 C9 H9C 109.5 . . H9A C9 H9B 109.5 . . H9A C9 H9C 109.5 . . H9B C9 H9C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Br1 C1 1.906(3) . O1 C3 1.359(4) . O1 C7 1.437(3) . O2 C4 1.379(3) . O2 C8 1.443(4) . O3 C5 1.363(3) . O3 C9 1.433(4) . C1 C2 1.386(4) . C1 C6 1.382(4) . C2 H2 0.9500 . C2 C3 1.397(4) . C3 C4 1.401(4) . C4 C5 1.400(4) . C5 C6 1.396(4) . C6 H6 0.9500 . C7 H7A 0.9800 . C7 H7B 0.9800 . C7 H7C 0.9800 . C8 H8A 0.9800 . C8 H8B 0.9800 . C8 H8C 0.9800 . C9 H9A 0.9800 . C9 H9B 0.9800 . C9 H9C 0.9800 . 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 Br1 C1 C2 C3 179.1(2) . . . . Br1 C1 C6 C5 -177.8(2) . . . . O1 C3 C4 O2 5.9(4) . . . . O1 C3 C4 C5 -175.8(3) . . . . O2 C4 C5 O3 -2.5(4) . . . . O2 C4 C5 C6 176.3(3) . . . . O3 C5 C6 C1 177.9(3) . . . . C1 C2 C3 O1 177.2(3) . . . . C1 C2 C3 C4 -1.8(4) . . . . C2 C1 C6 C5 2.4(5) . . . . C2 C3 C4 O2 -175.0(3) . . . . C2 C3 C4 C5 3.3(4) . . . . C3 C4 C5 O3 179.2(3) . . . . C3 C4 C5 C6 -2.0(4) . . . . C4 C5 C6 C1 -0.8(4) . . . . C6 C1 C2 C3 -1.1(5) . . . . C7 O1 C3 C2 4.5(4) . . . . C7 O1 C3 C4 -176.4(3) . . . . C8 O2 C4 C3 -99.4(3) . . . . C8 O2 C4 C5 82.3(3) . . . . C9 O3 C5 C4 -173.6(3) . . . . C9 O3 C5 C6 7.6(4) . . . . _cod_database_fobs_code 3500102