#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/38/2203828.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_2203828
loop_
_publ_author_name
'Andreas Fischer'
'Veronica M. Profir'
_publ_section_title
;
 A 2-propanol solvate of (RS)-phenylsuccinic acid
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o979
_journal_page_last               o981
_journal_paper_doi               10.1107/S160053680401061X
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C10 H10 O4, C3 H8 O'
_chemical_formula_moiety         'C10 H10 O4, C3 H8 O'
_chemical_formula_sum            'C13 H18 O5'
_chemical_formula_weight         254.282
_chemical_name_systematic        ?
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 123.93(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.460(10)
_cell_length_b                   5.467(2)
_cell_length_c                   21.477(6)
_cell_measurement_reflns_used    87
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      4.58
_cell_volume                     2577.8(18)
_computing_cell_refinement       'DORAX/LSQ (Duisenberg, 1992)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'maXus (Mackay et al., 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'Bruker--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  0.0825
_diffrn_reflns_av_sigmaI/netI    0.0666
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9953
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         4.58
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.238
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0577
_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)+(0.0296P)²+5.2191P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1314
_reflns_number_gt                1868
_reflns_number_total             2904
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6247.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2203828
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_type_symbol
C1 0.06370(9) 0.3862(5) 0.36450(11) 0.0170(5) Uani d . 1 C
C2 0.06261(10) 0.5824(5) 0.40512(12) 0.0208(5) Uani d . 1 C
C3 0.01926(11) 0.5926(5) 0.42248(13) 0.0243(5) Uani d . 1 C
C4 -0.02339(11) 0.4086(5) 0.39911(13) 0.0256(6) Uani d . 1 C
C5 -0.02184(10) 0.2102(5) 0.36020(13) 0.0244(5) Uani d . 1 C
O5 0.20871(7) 0.9047(4) 0.18904(9) 0.0297(4) Uani d . 1 O
C6 0.02158(10) 0.1993(5) 0.34316(12) 0.0209(5) Uani d . 1 C
C7 0.10902(9) 0.3797(4) 0.34211(11) 0.0171(5) Uani d . 1 C
C8 0.17189(10) 0.3283(4) 0.41117(12) 0.0174(5) Uani d . 1 C
C9 0.10704(10) 0.6173(5) 0.30385(12) 0.0191(5) Uani d . 1 C
C10 0.14661(9) 0.6170(5) 0.27371(11) 0.0182(5) Uani d . 1 C
C11 0.19829(13) 0.5668(6) 0.11004(16) 0.0398(7) Uani d . 1 C
C12 0.18594(11) 0.8355(5) 0.11298(13) 0.0268(6) Uani d . 1 C
C13 0.11943(12) 0.8978(6) 0.06612(14) 0.0348(7) Uani d . 1 C
O1 0.17908(7) 0.0979(3) 0.43163(9) 0.0264(4) Uani d . 1 O
O2 0.21051(7) 0.4850(3) 0.44506(9) 0.0246(4) Uani d . 1 O
O3 0.14622(7) 0.8326(3) 0.24652(9) 0.0264(4) Uani d . 1 O
O4 0.17434(7) 0.4404(3) 0.27452(9) 0.0278(4) Uani d . 1 O
H1O 0.2170 0.0693 0.4703 0.032 Uiso d R 1 H
H2 0.0935 0.6932 0.4219 0.025 Uiso d R 1 H
H3 0.0196 0.7409 0.4501 0.029 Uiso d R 1 H
H3O 0.1715 0.8269 0.2280 0.032 Uiso d R 1 H
H4 -0.0550 0.4098 0.4085 0.031 Uiso d R 1 H
H5 -0.0547 0.0965 0.3396 0.029 Uiso d R 1 H
H5O 0.2514 0.9148 0.2113 0.036 Uiso d R 1 H
H6 0.0264 0.0604 0.3162 0.025 Uiso d R 1 H
H7 0.0998 0.2486 0.3086 0.021 Uiso d R 1 H
H9A 0.1174 0.7575 0.3394 0.023 Uiso d R 1 H
H9B 0.0641 0.6299 0.2585 0.023 Uiso d R 1 H
H11A 0.2432 0.5449 0.1410 0.048 Uiso d R 1 H
H11B 0.1832 0.5041 0.0595 0.048 Uiso d R 1 H
H11C 0.1748 0.4727 0.1312 0.048 Uiso d R 1 H
H12 0.2101 0.9304 0.1000 0.032 Uiso d R 1 H
H13A 0.1039 0.8599 0.0135 0.042 Uiso d R 1 H
H13B 0.1138 1.0784 0.0693 0.042 Uiso d R 1 H
H13C 0.0948 0.8302 0.0832 0.042 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
O5 C12 C13 107.0(2) n
O5 C12 C11 109.8(2) n
C13 C12 C11 113.1(2) n
O4 C10 O3 125.4(2) n
O4 C10 C9 123.9(2) n
O3 C10 C9 110.8(2) n
C8 C7 C1 108.89(16) n
C8 C7 C9 112.03(19) n
C1 C7 C9 110.78(19) n
C6 C1 C2 118.7(2) n
C6 C1 C7 120.5(2) n
C2 C1 C7 120.8(2) n
C10 C9 C7 114.1(2) n
O2 C8 O1 124.0(2) n
O2 C8 C7 123.5(2) n
O1 C8 C7 112.4(2) n
C3 C2 C1 120.5(2) n
C4 C3 C2 120.2(2) n
C1 C6 C5 120.8(2) n
C4 C5 C6 120.0(2) n
C3 C4 C5 119.8(2) n
C12 O5 H5O 102.3 n
O5 C12 H12 104.9 n
C13 C12 H12 113.5 n
C11 C12 H12 108.2 n
C12 C13 H13A 107.7 n
C12 C13 H13B 109.9 n
H13A C13 H13B 107.5 n
C12 C13 H13C 116.1 n
H13A C13 H13C 114.3 n
H13B C13 H13C 101.0 n
C12 C11 H11A 107.1 n
C12 C11 H11B 114.8 n
H11A C11 H11B 107.1 n
C12 C11 H11C 104.8 n
H11A C11 H11C 114.5 n
H11B C11 H11C 108.8 n
C8 O1 H1O 111.0 n
C10 O3 H3O 108.9 n
C8 C7 H7 106.3 n
C1 C7 H7 110.2 n
C9 C7 H7 108.6 n
C10 C9 H9A 111.5 n
C7 C9 H9A 109.2 n
C10 C9 H9B 105.3 n
C7 C9 H9B 105.2 n
H9A C9 H9B 111.5 n
C3 C2 H2 123.9 n
C1 C2 H2 115.5 n
C4 C3 H3 122.7 n
C2 C3 H3 117.1 n
C1 C6 H6 114.2 n
C5 C6 H6 125.0 n
C4 C5 H5 117.7 n
C6 C5 H5 121.6 n
C3 C4 H4 123.2 n
C5 C4 H4 117.0 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O5 C12 1.441(3) n
C12 C13 1.500(3) n
C12 C11 1.514(4) n
O1 C8 1.312(3) n
O2 C8 1.216(3) n
O3 C10 1.313(3) n
O4 C10 1.207(3) n
C10 C9 1.508(3) n
C7 C8 1.514(3) n
C7 C1 1.521(3) n
C7 C9 1.522(3) n
C1 C6 1.388(3) n
C1 C2 1.393(3) n
C2 C3 1.391(3) n
C3 C4 1.380(4) n
C6 C5 1.388(3) n
C5 C4 1.384(4) n
O5 H5O 0.9508 n
C12 H12 0.9770 n
C13 H13A 0.9857 n
C13 H13B 1.0064 n
C13 H13C 0.9810 n
C11 H11A 0.9927 n
C11 H11B 0.9851 n
C11 H11C 1.0837 n
O1 H1O 0.8898 n
O3 H3O 0.9500 n
C7 H7 0.9461 n
C9 H9A 1.0051 n
C9 H9B 1.0044 n
C2 H2 0.9140 n
C3 H3 1.0018 n
C6 H6 1.0053 n
C5 H5 0.9530 n
C4 H4 0.9648 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
O1 H1O O2 7_556 0.89 1.78 2.668(2) 173
O3 H3O O5 . 0.95 1.67 2.587(2) 163
O5 H5O O4 4 0.95 1.82 2.743(2) 163
