#------------------------------------------------------------------------------ #$Date: 2016-07-12 09:09:45 +0300 (Tue, 12 Jul 2016) $ #$Revision: 184384 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/58/7225886.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_7225886 loop_ _publ_author_name 'Spaniol, Jacqueline M.' 'Wheeler, Kraig A.' _publ_section_title ; Accessing Centnerszwer's quasiracemate -- molecular shape controlled molecular recognition ; _journal_issue 69 _journal_name_full 'RSC Adv.' _journal_page_first 64921 _journal_paper_doi 10.1039/C6RA08131B _journal_volume 6 _journal_year 2016 _chemical_absolute_configuration rmad _chemical_formula_moiety 'C4 H5 Br O4' _chemical_formula_sum 'C4 H5 Br O4' _chemical_formula_weight 196.99 _chemical_melting_point 435.0(10) _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2016-03-25 deposited with the CCDC. 2016-06-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.5647(5) _cell_length_b 8.6337(7) _cell_length_c 9.2380(7) _cell_measurement_reflns_used 1803 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 67.87 _cell_measurement_theta_min 7.02 _cell_volume 603.35(8) _computing_cell_refinement APEX2 _computing_data_collection 'APEX2 (Bruker, 2014)' _computing_data_reduction ; SADABS (Bruker, 2013) and XPREP (Bruker, 2013) ; _computing_molecular_graphics 'XSEED (Barbour, 2001)' _computing_publication_material 'XSEED (Barbour, 2001)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.973 _diffrn_measured_fraction_theta_max 0.970 _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_unetI/netI 0.0361 _diffrn_reflns_Laue_measured_fraction_full 0.973 _diffrn_reflns_Laue_measured_fraction_max 0.970 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 4637 _diffrn_reflns_point_group_measured_fraction_full 0.959 _diffrn_reflns_point_group_measured_fraction_max 0.954 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.235 _diffrn_reflns_theta_min 7.020 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 8.870 _exptl_absorpt_correction_T_max 0.753 _exptl_absorpt_correction_T_min 0.475 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2014/7, Bruker AXS' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.169 _exptl_crystal_description 'transparent plate' _exptl_crystal_F_000 384 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.094 _exptl_crystal_size_mid 0.084 _exptl_crystal_size_min 0.033 _refine_diff_density_max 0.607 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.082 _refine_ls_abs_structure_details ; Flack x determined using 385 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.02(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 88 _refine_ls_number_reflns 1060 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.062 _refine_ls_R_factor_all 0.0284 _refine_ls_R_factor_gt 0.0264 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0284P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.0568 _reflns_Friedel_coverage 0.628 _reflns_Friedel_fraction_full 0.937 _reflns_Friedel_fraction_max 0.930 _reflns_number_gt 1010 _reflns_number_total 1060 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ra08131b2.cif _cod_data_source_block 14kaw14 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '434-436' was changed to '435.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas ; _cod_database_code 7225886 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.208 _shelx_estimated_absorpt_t_max 0.465 _shelx_res_file ; C:\14kaw14.res created by SHELXL-2014/7 REM 14kaw14 in P2(1)2(1)2(1) REM R1 = 0.0264 for 1010 Fo > 4sig(Fo) and 0.0284 for all 1060 data REM 88 parameters refined using 0 restraints REM Highest difference peak 0.610, deepest hole -0.347, 1-sigma level 0.082 REM 14kaw14 in P2(1)2(1)2(1) REM R1 = 0.0264 for 1010 Fo > 4sig(Fo) and 0.0284 for all 1060 data REM 88 parameters refined using 0 restraints REM Highest difference peak 0.608, deepest hole -0.349, 1-sigma level 0.082 TITL 14kaw14 in P2(1)2(1)2(1) CELL 1.54178 7.5647 8.6337 9.2380 90.000 90.000 90.000 ZERR 4.0000 0.0005 0.0007 0.0007 0.000 0.000 0.000 LATT -1 SYMM 0.5-X, -Y, 0.5+Z SYMM 0.5+X, 0.5-Y, -Z SYMM -X, 0.5+Y, 0.5-Z SFAC C H O BR UNIT 16 20 16 4 MERG 2 SHEL 99999.00 0.83 FMAP 2 GRID PLAN 20 TEMP -173 SIZE 0.102 0.24 0.258 BOND $H CONF DFIX 0.85 0.02 O1 H1 DFIX 0.85 0.02 O3 H3 EQIV $1 X-1, Y, Z EQIV $2 1+X, Y, Z HTAB O1 O4_$2 HTAB O3 O2_$1 L.S. 10 ACTA WGHT 0.028400 FVAR 0.23486 BR1 4 0.902818 0.277989 0.948909 11.00000 0.01760 0.03322 = 0.02334 0.00925 0.00264 0.00307 O1 3 1.228959 0.524920 0.857303 11.00000 0.01210 0.02784 = 0.02826 -0.00233 -0.00138 -0.00033 H1 2 1.336458 0.510902 0.836366 11.00000 -1.20000 O2 3 1.195459 0.353542 0.676473 11.00000 0.00936 0.03846 = 0.02453 -0.00829 0.00134 -0.00105 O3 3 0.536720 0.340270 0.611296 11.00000 0.00848 0.04073 = 0.02995 -0.01017 0.00139 -0.00202 H3 2 0.426299 0.350884 0.626069 11.00000 -1.20000 O4 3 0.571243 0.490831 0.807135 11.00000 0.01134 0.03152 = 0.02296 -0.00274 -0.00023 0.00289 C1 1 1.135660 0.436291 0.770981 11.00000 0.01462 0.02314 = 0.02009 0.00021 -0.00275 -0.00075 C2 1 0.939697 0.444299 0.802914 11.00000 0.01795 0.02149 = 0.02162 0.00422 0.00166 0.00031 AFIX 13 H2 2 0.908336 0.547553 0.844699 11.00000 -1.20000 AFIX 0 C3 1 0.826537 0.410091 0.672630 11.00000 0.01289 0.02764 = 0.02509 0.00125 0.00097 0.00118 AFIX 23 H3A 2 0.854046 0.485820 0.595377 11.00000 -1.20000 H3B 2 0.855843 0.305567 0.635669 11.00000 -1.20000 AFIX 0 C4 1 0.632408 0.417174 0.706112 11.00000 0.01943 0.02152 = 0.02135 0.00571 -0.00119 -0.00158 HKLF 4 REM 14kaw14 in P2(1)2(1)2(1) REM R1 = 0.0264 for 1010 Fo > 4sig(Fo) and 0.0284 for all 1060 data REM 88 parameters refined using 2 restraints END WGHT 0.0284 0.0000 REM Highest difference peak 0.607, deepest hole -0.350, 1-sigma level 0.082 Q1 1 0.8896 0.3682 1.0046 11.00000 0.05 0.61 Q2 1 0.8874 0.3639 0.8768 11.00000 0.05 0.43 Q3 1 0.8995 0.2236 1.0342 11.00000 0.05 0.34 Q4 1 0.8459 0.2052 0.8791 11.00000 0.05 0.33 Q5 1 0.8814 0.1443 0.9299 11.00000 0.05 0.32 Q6 1 0.9071 0.4786 0.7294 11.00000 0.05 0.30 Q7 1 0.9371 0.2124 0.8417 11.00000 0.05 0.29 Q8 1 0.5191 0.4153 0.8376 11.00000 0.05 0.27 Q9 1 1.0235 0.2225 0.9961 11.00000 0.05 0.26 Q10 1 1.1785 0.2978 0.7558 11.00000 0.05 0.26 Q11 1 0.9423 0.3422 0.7307 11.00000 0.05 0.26 Q12 1 0.7941 0.2398 0.9505 11.00000 0.05 0.26 Q13 1 0.6027 0.5234 0.8815 11.00000 0.05 0.25 Q14 1 1.3390 0.2863 0.8380 11.00000 0.05 0.24 Q15 1 0.5998 0.4852 0.7594 11.00000 0.05 0.24 Q16 1 0.6012 0.6272 0.7119 11.00000 0.05 0.24 Q17 1 1.2094 0.5986 0.7924 11.00000 0.05 0.22 Q18 1 1.3417 0.4042 0.9570 11.00000 0.05 0.22 Q19 1 0.4712 0.2461 0.8207 11.00000 0.05 0.21 Q20 1 1.2784 0.3816 0.5829 11.00000 0.05 0.21 ; _shelx_res_checksum 2191 _solvent_exptl_crystal_recrystallization_method acetone loop_ _space_group_symop_operation_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_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 Br1 Br 0.90282(7) 0.27799(7) 0.94891(7) 0.02472(19) Uani 1 1 d . . O1 O 1.2290(5) 0.5249(5) 0.8573(5) 0.0227(10) Uani 1 1 d D . H1 H 1.336(4) 0.511(8) 0.836(7) 0.027 Uiso 1 1 d D U O2 O 1.1955(5) 0.3535(5) 0.6765(4) 0.0241(10) Uani 1 1 d . . O3 O 0.5367(5) 0.3403(5) 0.6113(5) 0.0264(11) Uani 1 1 d D . H3 H 0.426(4) 0.351(7) 0.626(7) 0.032 Uiso 1 1 d D U O4 O 0.5712(5) 0.4908(5) 0.8071(4) 0.0219(10) Uani 1 1 d . . C1 C 1.1357(7) 0.4363(7) 0.7710(6) 0.0193(13) Uani 1 1 d . . C2 C 0.9397(7) 0.4443(7) 0.8029(6) 0.0204(13) Uani 1 1 d . . H2 H 0.9083 0.5476 0.8447 0.024 Uiso 1 1 calc R U C3 C 0.8265(7) 0.4101(7) 0.6726(6) 0.0219(14) Uani 1 1 d . . H3A H 0.8540 0.4858 0.5954 0.026 Uiso 1 1 calc R U H3B H 0.8558 0.3056 0.6357 0.026 Uiso 1 1 calc R U C4 C 0.6324(7) 0.4172(7) 0.7061(6) 0.0208(14) 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 Br1 0.0176(3) 0.0332(3) 0.0233(3) 0.0092(3) 0.0026(3) 0.0031(2) O1 0.0121(19) 0.028(3) 0.028(2) -0.002(2) -0.0014(18) -0.0003(17) O2 0.009(2) 0.038(3) 0.025(2) -0.008(2) 0.0013(17) -0.0011(18) O3 0.0085(19) 0.041(3) 0.030(2) -0.010(2) 0.0014(16) -0.0020(17) O4 0.011(2) 0.032(2) 0.023(2) -0.0027(19) -0.0002(17) 0.0029(18) C1 0.015(3) 0.023(3) 0.020(3) 0.000(3) -0.003(2) -0.001(2) C2 0.018(3) 0.021(3) 0.022(3) 0.004(2) 0.002(2) 0.000(2) C3 0.013(3) 0.028(4) 0.025(3) 0.001(3) 0.001(2) 0.001(2) C4 0.019(3) 0.022(3) 0.021(3) 0.006(3) -0.001(2) -0.002(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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 C1 O1 H1 107(5) C4 O3 H3 112(4) O2 C1 O1 125.4(5) O2 C1 C2 122.1(5) O1 C1 C2 112.5(5) C3 C2 C1 113.1(5) C3 C2 Br1 108.7(4) C1 C2 Br1 103.7(4) C3 C2 H2 110.4 C1 C2 H2 110.4 Br1 C2 H2 110.4 C4 C3 C2 112.5(5) C4 C3 H3A 109.1 C2 C3 H3A 109.1 C4 C3 H3B 109.1 C2 C3 H3B 109.1 H3A C3 H3B 107.8 O4 C4 O3 124.3(5) O4 C4 C3 123.3(5) O3 C4 C3 112.3(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C2 1.990(6) O1 C1 1.311(7) O1 H1 0.84(3) O2 C1 1.215(7) O3 C4 1.316(7) O3 H3 0.85(3) O4 C4 1.220(7) C1 C2 1.513(7) C2 C3 1.506(8) C2 H2 1.0000 C3 C4 1.502(7) C3 H3A 0.9900 C3 H3B 0.9900 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 0.84(3) 1.80(3) 2.647(5) 175(7) 1_655 O3 H3 O2 0.85(3) 1.81(3) 2.653(5) 172(6) 1_455 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 O2 C1 C2 C3 -28.3(9) O1 C1 C2 C3 152.8(5) O2 C1 C2 Br1 89.2(6) O1 C1 C2 Br1 -89.6(5) C1 C2 C3 C4 179.5(5) Br1 C2 C3 C4 65.0(6) C2 C3 C4 O4 23.4(9) C2 C3 C4 O3 -159.0(5)