#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/20/2202070.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2202070
loop_
_publ_author_name
'Andreas Fischer'
'Veronica M. Profir'
_publ_section_title
;
 (RS)-Phenylsuccinic acid
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o485
_journal_page_last               o487
_journal_paper_doi               10.1107/S1600536803005658
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C10 H10 O4'
_chemical_formula_moiety         'C10 H10 O4'
_chemical_formula_sum            'C10 H10 O4'
_chemical_formula_weight         194.186
_chemical_name_systematic
;
(RS)-phenylsuccinic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                102.82(5)
_cell_angle_beta                 94.10(14)
_cell_angle_gamma                100.50(9)
_cell_formula_units_Z            4
_cell_length_a                   5.428(12)
_cell_length_b                   10.368(6)
_cell_length_c                   17.625(9)
_cell_measurement_reflns_used    154
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.391
_cell_measurement_theta_min      4.232
_cell_volume                     944(2)
_computing_cell_refinement       'EvalCCD (Duisenberg, 1998)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EvalCCD (Duisenberg, 1998)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'maXus (Mackay et al., 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.799
_diffrn_measured_fraction_theta_max 0.799
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_sigmaI/netI    0.0771
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14054
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         4.61
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.292
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3445
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0464P)²+0.7275P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1334
_reflns_number_gt                2223
_reflns_number_total             3445
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6211.cif
_cod_data_source_block           I
_cod_original_cell_volume        944.(2)
_cod_database_code               2202070
_cod_database_fobs_code          2202070
loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
-X,-Y,-Z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.9239(5) 0.5664(3) 0.40993(15) 0.0185(6) Uani d . 1 . . C
C2 0.8656(4) 0.6240(3) 0.34009(14) 0.0191(6) Uani d . 1 . . C
C3 0.6931(5) 0.7255(3) 0.36170(14) 0.0212(6) Uani d . 1 . . C
C4 0.8243(5) 0.8446(3) 0.42450(15) 0.0197(6) Uani d . 1 . . C
C5 0.7569(4) 0.5110(3) 0.26821(14) 0.0195(6) Uani d . 1 . . C
C6 0.8921(5) 0.4912(3) 0.20376(15) 0.0228(6) Uani d . 1 . . C
C7 0.7971(5) 0.3881(3) 0.13808(15) 0.0273(6) Uani d . 1 . . C
C8 0.5674(5) 0.3039(3) 0.13622(15) 0.0266(6) Uani d . 1 . . C
C9 0.4297(5) 0.3227(3) 0.20025(16) 0.0262(6) Uani d . 1 . . C
C10 0.5238(5) 0.4258(3) 0.26592(15) 0.0229(6) Uani d . 1 . . C
C11 0.9419(5) 0.9179(3) 0.08494(15) 0.0218(6) Uani d . 1 . . C
C12 0.8988(5) 0.8579(3) 0.15487(15) 0.0219(6) Uani d . 1 . . C
C13 0.6222(5) 0.7821(3) 0.14725(15) 0.0234(6) Uani d . 1 . . C
C14 0.5678(5) 0.6596(3) 0.08050(15) 0.0229(6) Uani d . 1 . . C
C15 0.9685(4) 0.9705(3) 0.22895(14) 0.0196(6) Uani d . 1 . . C
C16 0.8325(5) 1.0741(3) 0.24376(16) 0.0257(6) Uani d . 1 . . C
C17 0.9015(5) 1.1779(3) 0.31043(17) 0.0297(7) Uani d . 1 . . C
C18 1.1056(5) 1.1794(3) 0.36340(16) 0.0273(6) Uani d . 1 . . C
C19 1.2413(5) 1.0762(3) 0.34896(15) 0.0275(6) Uani d . 1 . . C
C20 1.1724(5) 0.9727(3) 0.28243(15) 0.0238(6) Uani d . 1 . . C
O1 1.1525(3) 0.53905(19) 0.41591(10) 0.0232(4) Uani d . 1 . . O
O2 0.7673(3) 0.54591(18) 0.45501(10) 0.0226(4) Uani d . 1 . . O
O3 0.6901(3) 0.93933(19) 0.44148(11) 0.0281(5) Uani d . 1 . . O
O4 1.0372(3) 0.85106(18) 0.45636(11) 0.0251(4) Uani d . 1 . . O
O5 0.3420(3) 0.5859(2) 0.07813(11) 0.0302(5) Uani d . 1 . . O
O6 0.7207(3) 0.63323(19) 0.03416(11) 0.0272(5) Uani d . 1 . . O
O7 1.1799(3) 0.9357(2) 0.07038(11) 0.0278(5) Uani d . 1 . . O
O8 0.7717(3) 0.9502(2) 0.04812(11) 0.0257(5) Uani d . 1 . . O
H2 1.0152 0.6602 0.3215 0.023 Uiso d R 1 . . H
H3A 0.6318 0.7525 0.3125 0.025 Uiso d R 1 . . H
H3B 0.5500 0.6873 0.3797 0.025 Uiso d R 1 . . H
H6 1.0381 0.5427 0.2027 0.027 Uiso d R 1 . . H
H7 0.9080 0.3821 0.0972 0.033 Uiso d R 1 . . H
H8 0.5058 0.2285 0.0898 0.032 Uiso d R 1 . . H
H9 0.2714 0.2544 0.2023 0.031 Uiso d R 1 . . H
H10 0.4307 0.4323 0.3135 0.027 Uiso d R 1 . . H
H12 1.0270 0.7990 0.1693 0.026 Uiso d R 1 . . H
H13A 0.6104 0.7364 0.1950 0.028 Uiso d R 1 . . H
H13B 0.5021 0.8480 0.1322 0.028 Uiso d R 1 . . H
H16 0.6803 1.0775 0.2098 0.031 Uiso d R 1 . . H
H17 0.7923 1.2411 0.3154 0.036 Uiso d R 1 . . H
H18 1.1609 1.2651 0.4128 0.033 Uiso d R 1 . . H
H19 1.3787 1.0680 0.3898 0.033 Uiso d R 1 . . H
H20 1.2543 0.9000 0.2751 0.029 Uiso d R 1 . . H
H1O 1.1953 0.5008 0.4633 0.028 Uiso d R 1 . . H
H3O 0.7834 1.0230 0.4772 0.034 Uiso d R 1 . . H
H5O 0.3170 0.5074 0.0449 0.036 Uiso d R 1 . . H
H7O 1.2067 0.9860 0.0291 0.033 Uiso d R 1 . . H
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_
_diffrn_radiation_wavelength
0.71073
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O2 C1 O1 124.3(2) n
O2 C1 C2 121.6(2) n
O1 C1 C2 114.1(2) n
C5 C2 C1 110.5(2) n
C5 C2 C3 113.3(2) n
C1 C2 C3 109.5(2) n
C4 C3 C2 111.0(2) n
O4 C4 O3 124.8(3) n
O4 C4 C3 121.8(3) n
O3 C4 C3 113.4(2) n
C6 C5 C10 119.4(3) n
C6 C5 C2 119.6(2) n
C10 C5 C2 121.0(3) n
C7 C6 C5 120.5(3) n
C8 C7 C6 119.9(3) n
C7 C8 C9 120.2(3) n
C10 C9 C8 120.0(3) n
C9 C10 C5 120.0(3) n
O8 C11 O7 124.6(3) n
O8 C11 C12 122.3(2) n
O7 C11 C12 113.0(2) n
C11 C12 C15 108.7(2) n
C11 C12 C13 110.0(2) n
C15 C12 C13 112.1(2) n
C14 C13 C12 111.3(2) n
O6 C14 O5 125.2(3) n
O6 C14 C13 122.6(2) n
O5 C14 C13 112.2(3) n
C20 C15 C16 119.3(3) n
C20 C15 C12 120.1(2) n
C16 C15 C12 120.6(2) n
C17 C16 C15 120.1(3) n
C16 C17 C18 120.1(3) n
C17 C18 C19 119.9(3) n
C20 C19 C18 119.9(3) n
C19 C20 C15 120.6(3) n
C5 C2 H2 98.4 n
C1 C2 H2 111.0 n
C3 C2 H2 113.7 n
C4 C3 H3A 112.1 n
C2 C3 H3A 109.3 n
C4 C3 H3B 107.5 n
C2 C3 H3B 111.5 n
H3A C3 H3B 105.4 n
C7 C6 H6 117.3 n
C5 C6 H6 122.3 n
C8 C7 H7 126.4 n
C6 C7 H7 113.7 n
C7 C8 H8 118.9 n
C9 C8 H8 120.8 n
C10 C9 H9 118.8 n
C8 C9 H9 120.7 n
C9 C10 H10 118.9 n
C5 C10 H10 120.8 n
C11 C12 H12 117.0 n
C15 C12 H12 96.6 n
C13 C12 H12 111.8 n
C14 C13 H13A 100.4 n
C12 C13 H13A 105.6 n
C14 C13 H13B 105.5 n
C12 C13 H13B 107.7 n
H13A C13 H13B 125.8 n
C17 C16 H16 115.7 n
C15 C16 H16 124.1 n
C16 C17 H17 112.9 n
C18 C17 H17 126.9 n
C17 C18 H18 117.9 n
C19 C18 H18 122.0 n
C20 C19 H19 117.8 n
C18 C19 H19 121.9 n
C19 C20 H20 119.7 n
C15 C20 H20 119.6 n
C1 O1 H1O 115.0 n
C4 O3 H3O 113.9 n
C14 O5 H5O 113.3 n
C11 O7 H7O 111.2 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O2 . 1.226(4) n
C1 O1 . 1.325(4) n
C1 C2 . 1.521(4) n
C2 C5 . 1.520(4) n
C2 C3 . 1.536(4) n
C3 C4 . 1.490(4) n
C4 O4 . 1.232(4) n
C4 O3 . 1.321(3) n
C5 C6 . 1.393(4) n
C5 C10 . 1.397(4) n
C6 C7 . 1.383(4) n
C7 C8 . 1.379(5) n
C8 C9 . 1.395(4) n
C9 C10 . 1.382(4) n
C11 O8 . 1.229(4) n
C11 O7 . 1.323(4) n
C11 C12 . 1.513(4) n
C12 C15 . 1.518(4) n
C12 C13 . 1.544(5) n
C13 C14 . 1.495(4) n
C14 O6 . 1.229(4) n
C14 O5 . 1.313(4) n
C15 C20 . 1.395(4) n
C15 C16 . 1.400(4) n
C16 C17 . 1.381(4) n
C17 C18 . 1.392(5) n
C18 C19 . 1.394(4) n
C19 C20 . 1.378(4) n
C2 H2 . 0.9429 n
C3 H3A . 1.0205 n
C3 H3B . 0.9163 n
C6 H6 . 0.8753 n
C7 H7 . 0.9706 n
C8 H8 . 0.9867 n
C9 H9 . 1.0171 n
C10 H10 . 1.0059 n
C12 H12 . 1.0583 n
C13 H13A . 1.0545 n
C13 H13B . 1.0862 n
C16 H16 . 0.9960 n
C17 H17 . 0.9550 n
C18 H18 . 1.0769 n
C19 H19 . 1.0267 n
C20 H20 . 0.9326 n
O1 H1O . 1.0310 n
O3 H3O . 0.9784 n
O5 H5O . 0.8719 n
O7 H7O . 0.9886 n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1O O2 2_766 1.03 1.63 2.651(3) 171 yes
O3 H3O O4 2_776 0.98 1.65 2.620(4) 171 yes
O5 H5O O6 2_665 0.87 1.75 2.612(3) 170 yes
O7 H7O O8 2_775 0.99 1.64 2.625(3) 172 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 86155
