#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/81/2018110.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_2018110
loop_
_publ_author_name
'Hu, Qiao-Sheng'
'Zhang, Xiu-Zhi'
'Luo, Shu-Fen'
'Sun, Yu-Hui'
'Du, Zi-Yi'
_publ_section_title
;
 Two polymorphs of (2-carboxyethyl)(phenyl)phosphinic acid
;
_journal_coeditor_code           SF3148
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o195
_journal_page_last               o197
_journal_paper_doi               10.1107/S0108270111013163
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C9 H11 O4 P'
_chemical_formula_moiety         'C9 H11 O4 P'
_chemical_formula_sum            'C9 H11 O4 P'
_chemical_formula_weight         214.15
_chemical_name_common            '2-carboxyethyl(phenyl)phosphinc acid'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.49480(10)
_cell_length_b                   8.68300(10)
_cell_length_c                   21.3724(4)
_cell_measurement_reflns_used    1796
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.92
_cell_measurement_theta_min      3.83
_cell_volume                     1019.71(3)
_computing_cell_refinement       'SMART (Bruker, 2008)'
_computing_data_collection       'SMART (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  'SHELXTL (Bruker, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and 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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5497
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.241
_refine_ls_abs_structure_details 'Flack (1983), 893 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.09(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2326
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0383
_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)+(0.0436P)²+0.0664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0870
_reflns_number_gt                2089
_reflns_number_total             2326
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3148.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               2018110
_cod_database_fobs_code          2018110
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_type_symbol
_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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.32891(10) 0.68214(5) 0.41950(2) 0.02644(14) Uani d . 1 1 . .
C C1 0.2968(4) 0.6999(2) 0.33649(9) 0.0316(5) Uani d . 1 1 . .
C C2 0.4618(5) 0.6304(3) 0.29583(9) 0.0429(6) Uani d . 1 1 . .
H H2A 0.5972 0.5793 0.3117 0.051 Uiso calc R 1 1 . .
C C3 0.4240(6) 0.6374(3) 0.23175(11) 0.0586(8) Uani d . 1 1 . .
H H3A 0.5309 0.5884 0.2045 0.070 Uiso calc R 1 1 . .
C C4 0.2270(6) 0.7173(4) 0.20876(12) 0.0694(10) Uani d . 1 1 . .
H H4A 0.2027 0.7227 0.1657 0.083 Uiso calc R 1 1 . .
C C5 0.0661(6) 0.7893(4) 0.24807(12) 0.0717(9) Uani d . 1 1 . .
H H5A -0.0642 0.8447 0.2318 0.086 Uiso calc R 1 1 . .
C C6 0.0988(5) 0.7790(3) 0.31248(11) 0.0507(7) Uani d . 1 1 . .
H H6A -0.0123 0.8252 0.3394 0.061 Uiso calc R 1 1 . .
C C7 0.2012(4) 0.5020(2) 0.44335(10) 0.0330(5) Uani d . 1 1 . .
H H7A 0.2125 0.4936 0.4885 0.040 Uiso calc R 1 1 . .
H H7B 0.0301 0.5002 0.4322 0.040 Uiso calc R 1 1 . .
C C8 0.3268(5) 0.3637(2) 0.41376(10) 0.0361(5) Uani d . 1 1 . .
H H8A 0.3263 0.3759 0.3686 0.043 Uiso calc R 1 1 . .
H H8B 0.4951 0.3611 0.4274 0.043 Uiso calc R 1 1 . .
C C9 0.2073(5) 0.2134(2) 0.43020(9) 0.0342(5) Uani d . 1 1 . .
O O1 0.6099(3) 0.67442(18) 0.42966(6) 0.0382(4) Uani d D 1 1 . .
H H1A 0.644(5) 0.679(3) 0.4666(5) 0.046 Uiso d D 1 1 . .
O O2 0.2054(3) 0.81281(14) 0.45275(6) 0.0345(4) Uani d . 1 1 . .
O O3 0.0050(3) 0.20158(19) 0.45074(8) 0.0536(5) Uani d . 1 1 . .
O O4 0.3510(4) 0.09573(15) 0.41730(8) 0.0520(5) Uani d D 1 1 . .
H H4B 0.285(5) 0.020(2) 0.4328(12) 0.062 Uiso d D 1 1 . .
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'
P P 0.1023 0.0942 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 P1 O1 . . 114.47(9) ?
O2 P1 C7 . . 110.40(9) ?
O1 P1 C7 . . 108.12(10) ?
O2 P1 C1 . . 111.08(9) ?
O1 P1 C1 . . 103.83(10) ?
C7 P1 C1 . . 108.61(10) ?
C6 C1 C2 . . 119.7(2) ?
C6 C1 P1 . . 119.16(17) ?
C2 C1 P1 . . 121.12(17) ?
C3 C2 C1 . . 120.0(2) ?
C3 C2 H2A . . 120.0 ?
C1 C2 H2A . . 120.0 ?
C4 C3 C2 . . 119.5(3) ?
C4 C3 H3A . . 120.2 ?
C2 C3 H3A . . 120.2 ?
C5 C4 C3 . . 121.2(2) ?
C5 C4 H4A . . 119.4 ?
C3 C4 H4A . . 119.4 ?
C4 C5 C6 . . 119.6(3) ?
C4 C5 H5A . . 120.2 ?
C6 C5 H5A . . 120.2 ?
C1 C6 C5 . . 120.0(3) ?
C1 C6 H6A . . 120.0 ?
C5 C6 H6A . . 120.0 ?
C8 C7 P1 . . 113.17(15) ?
C8 C7 H7A . . 108.9 ?
P1 C7 H7A . . 108.9 ?
C8 C7 H7B . . 108.9 ?
P1 C7 H7B . . 108.9 ?
H7A C7 H7B . . 107.8 ?
C9 C8 C7 . . 112.94(18) ?
C9 C8 H8A . . 109.0 ?
C7 C8 H8A . . 109.0 ?
C9 C8 H8B . . 109.0 ?
C7 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
O3 C9 O4 . . 124.3(2) ?
O3 C9 C8 . . 124.4(2) ?
O4 C9 C8 . . 111.22(19) ?
P1 O1 H1A . . 111.3(18) ?
C9 O4 H4B . . 106(2) ?
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
P1 O2 . 1.5010(14) yes
P1 O1 . 1.5605(16) yes
P1 C7 . 1.788(2) ?
P1 C1 . 1.7896(19) ?
C1 C6 . 1.385(3) ?
C1 C2 . 1.393(3) ?
C2 C3 . 1.387(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.377(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.370(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.391(3) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 C8 . 1.523(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.502(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 O3 . 1.200(3) yes
C9 O4 . 1.321(3) yes
O1 H1A . 0.814(10) ?
O4 H4B . 0.818(10) ?
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 H1A O2 4_566 0.814(10) 1.757(10) 2.5699(18) 177(3)
O4 H4B O2 1_545 0.818(10) 1.903(13) 2.6925(19) 162(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9462327
2 PubChem 11287340
