#------------------------------------------------------------------------------
#$Date: 2023-02-09 11:50:03 +0200 (Thu, 09 Feb 2023) $
#$Revision: 280841 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106738.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_8106738
loop_
_publ_author_name
'Zhang, Yun-Peng'
'Li, Bing'
_publ_section_title
;
 The crystal structure of (S)-2-benzylsuccinic acid, C11H12O4
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              975
_journal_page_last               976
_journal_paper_doi               10.1515/ncrs-2017-0106
_journal_volume                  232
_journal_year                    2017
_chemical_absolute_configuration rm
_chemical_formula_sum            'C11 H12 O4'
_chemical_formula_weight         208.21
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.922(2)
_cell_length_b                   9.960(2)
_cell_length_c                   10.967(2)
_cell_measurement_reflns_used    2468
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.440
_cell_measurement_theta_min      3.44
_cell_volume                     1083.8(4)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10615
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.44
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_coef       0.030(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0779P)²+0.3609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1861
_reflns_number_gt                1466
_reflns_number_total             2468
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0106_suppl.cif
_cod_data_source_block           3
_cod_original_cell_volume        1083.9(4)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               8106738
_check                           for
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
O4 O 0.7878(2) 0.3354(2) 0.4531(2) 0.0644(7) Uani 1 1 d . . .
H4A H 0.8434 0.2755 0.4631 0.097 Uiso 1 1 calc R . .
O3 O 0.8093(3) 0.3531(3) 0.6540(2) 0.0717(8) Uani 1 1 d . . .
O2 O 0.4629(3) 0.3607(2) 0.5359(2) 0.0642(7) Uani 1 1 d . . .
O1 O 0.4610(3) 0.3699(3) 0.3337(2) 0.0789(9) Uani 1 1 d . . .
H1A H 0.4154 0.3020 0.3425 0.118 Uiso 1 1 calc R . .
C4 C 0.7670(3) 0.3959(3) 0.5545(3) 0.0532(7) Uani 1 1 d . . .
C6 C 0.7307(3) 0.7790(3) 0.5490(3) 0.0523(8) Uani 1 1 d . . .
C2 C 0.5946(3) 0.5294(3) 0.4387(4) 0.0568(8) Uani 1 1 d . . .
H2A H 0.5426 0.6118 0.4409 0.068 Uiso 1 1 calc R . .
H2B H 0.6467 0.5292 0.3638 0.068 Uiso 1 1 calc R . .
C1 C 0.4999(3) 0.4121(3) 0.4377(3) 0.0514(7) Uani 1 1 d . . .
C3 C 0.6909(3) 0.5270(3) 0.5471(3) 0.0511(7) Uani 1 1 d . . .
H3A H 0.6381 0.5377 0.6220 0.061 Uiso 1 1 calc R . .
C11 C 0.7159(4) 0.8596(3) 0.4482(4) 0.0648(9) Uani 1 1 d . . .
H11A H 0.7449 0.8289 0.3725 0.078 Uiso 1 1 calc R . .
C7 C 0.6860(4) 0.8261(4) 0.6591(3) 0.0697(11) Uani 1 1 d . . .
H7A H 0.6956 0.7731 0.7283 0.084 Uiso 1 1 calc R . .
C5 C 0.7958(3) 0.6421(3) 0.5406(4) 0.0609(9) Uani 1 1 d . . .
H5A H 0.8599 0.6320 0.6068 0.073 Uiso 1 1 calc R . .
H5B H 0.8451 0.6355 0.4644 0.073 Uiso 1 1 calc R . .
C10 C 0.6587(4) 0.9857(4) 0.4576(5) 0.0763(11) Uani 1 1 d . . .
H10A H 0.6504 1.0393 0.3886 0.092 Uiso 1 1 calc R . .
C8 C 0.6263(5) 0.9523(4) 0.6689(4) 0.0788(12) Uani 1 1 d . . .
H8A H 0.5948 0.9826 0.7438 0.095 Uiso 1 1 calc R . .
C9 C 0.6144(4) 1.0317(3) 0.5671(5) 0.0744(11) Uani 1 1 d . . .
H9A H 0.5762 1.1167 0.5731 0.089 Uiso 1 1 calc R . .
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'
O O 0.0106 0.0060 '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
C4 O4 H4A 109.5 . .
C1 O1 H1A 109.5 . .
O3 C4 O4 123.1(3) . .
O3 C4 C3 120.7(3) . .
O4 C4 C3 116.1(3) . .
C7 C6 C11 118.3(3) . .
C7 C6 C5 120.1(3) . .
C11 C6 C5 121.6(3) . .
C1 C2 C3 112.7(3) . .
C1 C2 H2A 109.1 . .
C3 C2 H2A 109.1 . .
C1 C2 H2B 109.1 . .
C3 C2 H2B 109.1 . .
H2A C2 H2B 107.8 . .
O2 C1 O1 123.3(3) . .
O2 C1 C2 119.8(3) . .
O1 C1 C2 116.9(3) . .
C4 C3 C2 111.6(3) . .
C4 C3 C5 107.8(3) . .
C2 C3 C5 111.9(3) . .
C4 C3 H3A 108.5 . .
C2 C3 H3A 108.5 . .
C5 C3 H3A 108.5 . .
C6 C11 C10 121.0(4) . .
C6 C11 H11A 119.5 . .
C10 C11 H11A 119.5 . .
C6 C7 C8 121.0(3) . .
C6 C7 H7A 119.5 . .
C8 C7 H7A 119.5 . .
C6 C5 C3 112.1(3) . .
C6 C5 H5A 109.2 . .
C3 C5 H5A 109.2 . .
C6 C5 H5B 109.2 . .
C3 C5 H5B 109.2 . .
H5A C5 H5B 107.9 . .
C9 C10 C11 120.4(4) . .
C9 C10 H10A 119.8 . .
C11 C10 H10A 119.8 . .
C9 C8 C7 119.5(4) . .
C9 C8 H8A 120.2 . .
C7 C8 H8A 120.2 . .
C10 C9 C8 119.8(3) . .
C10 C9 H9A 120.1 . .
C8 C9 H9A 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O4 C4 1.281(4) .
O4 H4A 0.8200 .
O3 C4 1.244(4) .
O2 C1 1.248(4) .
O1 C1 1.275(4) .
O1 H1A 0.8200 .
C4 C3 1.511(4) .
C6 C7 1.369(5) .
C6 C11 1.374(5) .
C6 C5 1.512(4) .
C2 C1 1.500(4) .
C2 C3 1.526(5) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C5 1.550(4) .
C3 H3A 0.9800 .
C11 C10 1.382(5) .
C11 H11A 0.9300 .
C7 C8 1.394(5) .
C7 H7A 0.9300 .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C10 C9 1.358(6) .
C10 H10A 0.9300 .
C8 C9 1.373(6) .
C8 H8A 0.9300 .
C9 H9A 0.9300 .
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
O4 H4A O2 0.82 1.80 2.617(3) 172.4 4_556
O1 H1A O3 0.82 1.87 2.687(4) 174.4 4_456
