#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/58/7225885.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_7225885
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 Cl O4'
_chemical_formula_sum            'C4 H5 Cl O4'
_chemical_formula_weight         152.53
_chemical_melting_point          446.0(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                   7.5593(3)
_cell_length_b                   8.5020(3)
_cell_length_c                   9.0604(4)
_cell_measurement_reflns_used    5909
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      7.14
_cell_volume                     582.30(4)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0380
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8317
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.216
_diffrn_reflns_theta_min         7.143
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    5.371
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_description       'transparent plate'
_exptl_crystal_F_000             312
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     89
_refine_ls_number_reflns         1068
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0400
_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)+(0.0577P)²+0.5716P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1029
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1060
_reflns_number_total             1068
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ra08131b2.cif
_cod_data_source_block           14kaw13
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '445-447' was changed to '446.0(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               7225885
_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_res_file
;

    C:\14kaw13.res created by SHELXL-2014/7

REM  14kaw13 in P2(1)2(1)2(1)
REM R1 =  0.0405 for    1060 Fo > 4sig(Fo)  and  0.0406 for all    1068 data
REM     90 parameters refined using      0 restraints
REM Highest difference peak  0.621,  deepest hole -0.239,  1-sigma level  0.086
REM  14kaw13 in P2(1)2(1)2(1)
REM R1 =  0.0402 for    1060 Fo > 4sig(Fo)  and  0.0404 for all    1068 data
REM     88 parameters refined using      2 restraints
REM Highest difference peak  0.613,  deepest hole -0.244,  1-sigma level  0.085
TITL 14kaw13 in P2(1)2(1)2(1)
CELL 1.54178 7.5593 8.5020 9.0604 90.000 90.000 90.000
ZERR 4.0000 0.0003 0.0003 0.0004 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 CL
UNIT 16 20 16 4
MERG 2
FMAP 2
GRID
PLAN 20
TEMP -100
DFIX 0.85 0.02 O1 H1
DFIX 0.85 0.02 O3 H3
BOND $H
CONF
TWIN
L.S. 10
ACTA
WGHT    0.057700    0.571600
BASF   0.08367
FVAR       0.32328
CL1   4    0.100029    0.717063    0.054219    11.00000    0.02033    0.04292 =
         0.03532    0.01580    0.00466    0.00449
O1    3   -0.227425    0.473908    0.133252    11.00000    0.01044    0.03368 =
         0.04047   -0.00588   -0.00201   -0.00070
H1    2   -0.337652    0.478608    0.143297    11.00000   -1.20000
O2    3   -0.194187    0.651654    0.312385    11.00000    0.01095    0.04616 =
         0.03387   -0.00988    0.00136   -0.00113
O3    3    0.463432    0.660072    0.381131    11.00000    0.01184    0.03873 =
         0.03780   -0.00888    0.00014   -0.00380
H3    2    0.570748    0.651838    0.355969    11.00000   -1.20000
O4    3    0.429058    0.506591    0.182042    11.00000    0.01158    0.03540 =
         0.03020   -0.00158   -0.00063    0.00150
C1    1   -0.136218    0.564987    0.218898    11.00000    0.01209    0.02839 =
         0.02375    0.00096    0.00017   -0.00188
C2    1    0.061868    0.557495    0.185541    11.00000    0.01390    0.03287 =
         0.03131    0.00469   -0.00015    0.00164
AFIX  13
H2    2    0.092558    0.454037    0.139702    11.00000   -1.20000
AFIX   0
C3    1    0.173133    0.585420    0.319214    11.00000    0.01225    0.03298 =
         0.03328   -0.00324   -0.00054   -0.00115
AFIX  23
H3A   2    0.146073    0.504012    0.394007    11.00000   -1.20000
H3B   2    0.142632    0.689097    0.361955    11.00000   -1.20000
AFIX   0
C4    1    0.369246    0.581546    0.284859    11.00000    0.01500    0.02571 =
         0.02865    0.00277   -0.00075    0.00172
HKLF 4

REM  14kaw13 in P2(1)2(1)2(1)
REM R1 =  0.0400 for    1060 Fo > 4sig(Fo)  and  0.0401 for all    1068 data
REM     89 parameters refined using      2 restraints

END

WGHT      0.0577      0.5689

REM Highest difference peak  0.613,  deepest hole -0.242,  1-sigma level  0.085
Q1    1   0.1489  0.7904  0.1138  11.00000  0.05    0.61
Q2    1   0.1006  0.6374 -0.0163  11.00000  0.05    0.56
Q3    1   0.1019  0.6287  0.1145  11.00000  0.05    0.45
Q4    1   0.0613  0.4894  0.2575  11.00000  0.05    0.39
Q5    1   0.1024  0.7890 -0.0138  11.00000  0.05    0.35
Q6    1   0.1643  0.6462  0.2493  11.00000  0.05    0.34
Q7    1  -0.2162  0.4063  0.1986  11.00000  0.05    0.31
Q8    1   0.4417  0.4379  0.2358  11.00000  0.05    0.28
Q9    1   0.4175  0.4460  0.1267  11.00000  0.05    0.27
Q10   1   0.4384  0.7299  0.4425  11.00000  0.05    0.24
Q11   1  -0.1886  0.7248  0.2454  11.00000  0.05    0.24
Q12   1   0.4487  0.7194  0.3071  11.00000  0.05    0.23
Q13   1  -0.1435  0.5183  0.2706  11.00000  0.05    0.23
Q14   1   0.3872  0.6344  0.2123  11.00000  0.05    0.22
Q15   1   0.3535  0.4966  0.2042  11.00000  0.05    0.22
Q16   1   0.4634  0.5614  0.1562  11.00000  0.05    0.22
Q17   1   0.4799  0.5804  0.3073  11.00000  0.05    0.20
Q18   1  -0.1681  0.7233  0.3709  11.00000  0.05    0.20
Q19   1  -0.1364  0.6742  0.2800  11.00000  0.05    0.19
Q20   1  -0.2224  0.5616  0.2614  11.00000  0.05    0.19
;
_shelx_res_checksum              58051
_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
Cl1 Cl 0.10003(14) 0.71706(13) 0.05422(12) 0.0329(3) Uani 1 1 d . .
O1 O -0.2274(4) 0.4739(4) 0.1333(4) 0.0282(7) Uani 1 1 d D .
H1 H -0.338(3) 0.479(7) 0.143(6) 0.034 Uiso 1 1 d D U
O2 O -0.1942(4) 0.6517(4) 0.3124(4) 0.0303(8) Uani 1 1 d . .
O3 O 0.4634(4) 0.6601(4) 0.3811(4) 0.0295(7) Uani 1 1 d D .
H3 H 0.571(4) 0.652(7) 0.356(6) 0.035 Uiso 1 1 d D U
O4 O 0.4291(3) 0.5066(4) 0.1820(3) 0.0257(7) Uani 1 1 d . .
C1 C -0.1362(5) 0.5650(5) 0.2189(5) 0.0214(8) Uani 1 1 d . .
C2 C 0.0619(5) 0.5575(5) 0.1855(5) 0.0260(9) Uani 1 1 d . .
H2 H 0.0926 0.4540 0.1397 0.031 Uiso 1 1 calc R U
C3 C 0.1731(5) 0.5854(5) 0.3192(5) 0.0262(9) Uani 1 1 d . .
H3A H 0.1461 0.5040 0.3940 0.031 Uiso 1 1 calc R U
H3B H 0.1426 0.6891 0.3620 0.031 Uiso 1 1 calc R U
C4 C 0.3692(5) 0.5815(5) 0.2849(5) 0.0231(9) 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
Cl1 0.0203(5) 0.0429(6) 0.0353(6) 0.0158(5) 0.0047(4) 0.0045(4)
O1 0.0104(13) 0.0337(17) 0.0405(17) -0.0059(14) -0.0020(12) -0.0007(12)
O2 0.0109(13) 0.0462(18) 0.0339(17) -0.0099(15) 0.0014(12) -0.0011(13)
O3 0.0118(13) 0.0387(17) 0.0378(17) -0.0089(15) 0.0001(12) -0.0038(13)
O4 0.0116(13) 0.0354(15) 0.0302(16) -0.0016(14) -0.0006(11) 0.0015(12)
C1 0.0121(18) 0.0284(19) 0.024(2) 0.0010(17) 0.0002(15) -0.0019(15)
C2 0.0139(19) 0.033(2) 0.031(2) 0.0047(19) -0.0001(16) 0.0016(17)
C3 0.0122(18) 0.033(2) 0.033(2) -0.0032(19) -0.0005(17) -0.0011(16)
C4 0.0150(19) 0.0257(19) 0.029(2) 0.0028(17) -0.0007(16) 0.0017(16)
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'
Cl Cl 0.3639 0.7018 '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 116(4)
C4 O3 H3 107(4)
O2 C1 O1 126.4(4)
O2 C1 C2 121.4(4)
O1 C1 C2 112.2(4)
C3 C2 C1 112.6(4)
C3 C2 Cl1 108.7(3)
C1 C2 Cl1 104.6(3)
C3 C2 H2 110.2
C1 C2 H2 110.2
Cl1 C2 H2 110.2
C2 C3 C4 112.4(4)
C2 C3 H3A 109.1
C4 C3 H3A 109.1
C2 C3 H3B 109.1
C4 C3 H3B 109.1
H3A C3 H3B 107.9
O4 C4 O3 125.1(4)
O4 C4 C3 122.2(4)
O3 C4 C3 112.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.827(5)
O1 C1 1.295(5)
O1 H1 0.84(3)
O2 C1 1.205(5)
O3 C4 1.309(5)
O3 H3 0.85(3)
O4 C4 1.216(5)
C1 C2 1.529(5)
C2 C3 1.494(6)
C2 H2 1.0000
C3 C4 1.515(6)
C3 H3A 0.9900
C3 H3B 0.9900
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 32.8(6)
O1 C1 C2 C3 -149.4(4)
O2 C1 C2 Cl1 -85.1(5)
O1 C1 C2 Cl1 92.7(4)
C1 C2 C3 C4 -178.7(4)
Cl1 C2 C3 C4 -63.2(4)
C2 C3 C4 O4 -26.9(6)
C2 C3 C4 O3 156.3(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 9793861
