#------------------------------------------------------------------------------
#$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/[σ²(Fo²)+(0.0284P)²] where P=(Fo²+2Fc²)/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 > 2σ(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)
