#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/98/2229804.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_2229804
loop_
_publ_author_name
'Karthikeyan, S.'
'Sethusankar, K.'
'Rajeshwaran, Ganesan Gobi'
'Mohanakrishnan, Arasambattu K.'
_publ_section_title
;
 4-[(Diethoxyphosphinoyl)methyl]benzoic acid
;
_journal_coeditor_code           PV2396
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o831
_journal_paper_doi               10.1107/S1600536811008282
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H17 O5 P'
_chemical_formula_moiety         'C12 H17 O5 P'
_chemical_formula_sum            'C12 H17 O5 P'
_chemical_formula_weight         272.23
_chemical_name_systematic
;
4-[(Diethoxyphosphinoyl)methyl]benzoic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 108.926(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6505(5)
_cell_length_b                   12.1706(6)
_cell_length_c                   11.8156(6)
_cell_measurement_reflns_used    2960
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      0.998
_cell_volume                     1312.75(12)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008), PARST (Nardelli, 1983) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEXII area-detector'
_diffrn_measurement_method       ω
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13181
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.32
_diffrn_reflns_theta_min         2.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0349
_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)+(0.0578P)²+0.2720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                2441
_reflns_number_total             2960
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2396.cif
_cod_data_source_block           I
_cod_original_cell_volume        1312.74(12)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229804
_cod_database_fobs_code          2229804
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
C C1 0.56048(16) -0.02314(13) 0.81418(13) 0.0410(3) Uani d . 1 . .
C C2 0.40996(15) 0.00742(12) 0.81102(12) 0.0367(3) Uani d . 1 . .
C C3 0.34611(17) 0.10233(13) 0.75114(14) 0.0430(3) Uani d . 1 . .
H H3 0.3950 0.1433 0.7094 0.052 Uiso calc R 1 . .
C C4 0.21059(18) 0.13606(14) 0.75341(14) 0.0451(4) Uani d . 1 . .
H H4 0.1691 0.2000 0.7135 0.054 Uiso calc R 1 . .
C C5 0.13554(16) 0.07576(13) 0.81447(13) 0.0409(3) Uani d . 1 . .
C C6 0.19754(18) -0.02041(14) 0.87045(14) 0.0457(4) Uani d . 1 . .
H H6 0.1467 -0.0632 0.9090 0.055 Uiso calc R 1 . .
C C7 0.33374(18) -0.05359(13) 0.86979(13) 0.0426(3) Uani d . 1 . .
H H7 0.3748 -0.1177 0.9093 0.051 Uiso calc R 1 . .
C C8 -0.00843(17) 0.11637(15) 0.82358(14) 0.0485(4) Uani d . 1 . .
H H8A -0.0678 0.0540 0.8304 0.058 Uiso calc R 1 . .
H H8B -0.0611 0.1561 0.7512 0.058 Uiso calc R 1 . .
C C9 -0.24479(18) 0.29083(16) 0.86037(16) 0.0536(4) Uani d . 1 . .
H H9A -0.2711 0.2456 0.7889 0.064 Uiso calc R 1 . .
H H9B -0.2059 0.3599 0.8428 0.064 Uiso calc R 1 . .
C C10 -0.3748(2) 0.31113(17) 0.89678(18) 0.0623(5) Uani d . 1 . .
H H10A -0.4147 0.2423 0.9110 0.094 Uiso calc R 1 . .
H H10B -0.4470 0.3501 0.8344 0.094 Uiso calc R 1 . .
H H10C -0.3473 0.3542 0.9687 0.094 Uiso calc R 1 . .
C C11 0.1723(2) 0.38949(16) 0.99414(17) 0.0558(4) Uani d . 1 . .
H H11A 0.1735 0.3721 1.0746 0.067 Uiso calc R 1 . .
H H11B 0.1314 0.4625 0.9740 0.067 Uiso calc R 1 . .
C C12 0.3235(2) 0.38617(19) 0.98815(19) 0.0662(5) Uani d . 1 . .
H H12A 0.3629 0.3135 1.0074 0.099 Uiso calc R 1 . .
H H12B 0.3837 0.4377 1.0443 0.099 Uiso calc R 1 . .
H H12C 0.3217 0.4051 0.9088 0.099 Uiso calc R 1 . .
O O1 0.10809(12) 0.15721(11) 1.06524(9) 0.0519(3) Uani d . 1 . .
O O2 -0.13529(11) 0.23494(10) 0.95801(9) 0.0451(3) Uani d . 1 . .
O O3 0.08356(12) 0.30987(10) 0.91015(10) 0.0502(3) Uani d . 1 . .
O O4 0.60874(12) -0.11402(10) 0.87523(10) 0.0513(3) Uani d . 1 . .
H H4A 0.6917 -0.1275 0.8744 0.077 Uiso calc R 1 . .
O O5 0.63179(14) 0.02983(11) 0.76684(12) 0.0608(3) Uani d . 1 . .
P P1 0.01894(4) 0.20435(4) 0.95001(3) 0.04038(14) Uani d . 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
O5 C1 O4 . . 123.27(14) ?
O5 C1 C2 . . 123.67(15) ?
O4 C1 C2 . . 113.06(13) ?
C7 C2 C3 . . 118.85(14) ?
C7 C2 C1 . . 121.87(14) ?
C3 C2 C1 . . 119.24(13) ?
C4 C3 C2 . . 120.27(14) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 120.74(15) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C6 C5 C4 . . 118.64(14) ?
C6 C5 C8 . . 120.56(15) ?
C4 C5 C8 . . 120.76(15) ?
C7 C6 C5 . . 120.77(14) ?
C7 C6 H6 . . 119.6 ?
C5 C6 H6 . . 119.6 ?
C6 C7 C2 . . 120.68(14) ?
C6 C7 H7 . . 119.7 ?
C2 C7 H7 . . 119.7 ?
C5 C8 P1 . . 111.44(10) ?
C5 C8 H8A . . 109.3 ?
P1 C8 H8A . . 109.3 ?
C5 C8 H8B . . 109.3 ?
P1 C8 H8B . . 109.3 ?
H8A C8 H8B . . 108.0 ?
O2 C9 C10 . . 108.36(14) ?
O2 C9 H9A . . 110.0 ?
C10 C9 H9A . . 110.0 ?
O2 C9 H9B . . 110.0 ?
C10 C9 H9B . . 110.0 ?
H9A C9 H9B . . 108.4 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O3 C11 C12 . . 108.69(15) ?
O3 C11 H11A . . 110.0 ?
C12 C11 H11A . . 110.0 ?
O3 C11 H11B . . 110.0 ?
C12 C11 H11B . . 110.0 ?
H11A C11 H11B . . 108.3 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C9 O2 P1 . . 121.53(10) ?
C11 O3 P1 . . 123.12(11) ?
C1 O4 H4A . . 109.5 ?
O1 P1 O3 . . 115.34(7) ?
O1 P1 O2 . . 108.59(6) ?
O3 P1 O2 . . 107.59(7) ?
O1 P1 C8 . . 115.07(8) ?
O3 P1 C8 . . 101.85(8) ?
O2 P1 C8 . . 107.89(7) ?
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 O5 . 1.2049(19) ?
C1 O4 . 1.3201(19) ?
C1 C2 . 1.488(2) ?
C2 C7 . 1.381(2) ?
C2 C3 . 1.390(2) ?
C3 C4 . 1.379(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.387(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.382(2) ?
C5 C8 . 1.511(2) ?
C6 C7 . 1.377(2) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 P1 . 1.7867(16) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 O2 . 1.4558(18) ?
C9 C10 . 1.473(2) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 O3 . 1.451(2) ?
C11 C12 . 1.484(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
O1 P1 . 1.4708(11) ?
O2 P1 . 1.5666(11) ?
O3 P1 . 1.5654(12) ?
O4 H4A . 0.8200 ?
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
O4 H4A O1 3_657 0.82 1.87 2.644(2) 158
C12 H12C Cg1 2_556 0.96 2.97 3.853(2) 153
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O5 C1 C2 C7 . . . . -177.82(15) ?
O4 C1 C2 C7 . . . . 1.6(2) ?
O5 C1 C2 C3 . . . . -0.3(2) ?
O4 C1 C2 C3 . . . . 179.10(13) ?
C7 C2 C3 C4 . . . . 1.7(2) ?
C1 C2 C3 C4 . . . . -175.88(14) ?
C2 C3 C4 C5 . . . . -0.4(2) ?
C3 C4 C5 C6 . . . . -1.7(2) ?
C3 C4 C5 C8 . . . . 176.10(14) ?
C4 C5 C6 C7 . . . . 2.6(2) ?
C8 C5 C6 C7 . . . . -175.21(14) ?
C5 C6 C7 C2 . . . . -1.4(2) ?
C3 C2 C7 C6 . . . . -0.8(2) ?
C1 C2 C7 C6 . . . . 176.70(13) ?
C6 C5 C8 P1 . . . . 89.85(17) ?
C4 C5 C8 P1 . . . . -87.88(16) ?
C10 C9 O2 P1 . . . . -178.09(13) ?
C12 C11 O3 P1 . . . . 113.06(15) ?
C11 O3 P1 O1 . . . . -31.60(15) ?
C11 O3 P1 O2 . . . . 89.74(13) ?
C11 O3 P1 C8 . . . . -156.94(13) ?
C9 O2 P1 O1 . . . . 175.49(13) ?
C9 O2 P1 O3 . . . . 50.02(14) ?
C9 O2 P1 C8 . . . . -59.17(15) ?
C5 C8 P1 O1 . . . . -54.31(15) ?
C5 C8 P1 O3 . . . . 71.21(13) ?
C5 C8 P1 O2 . . . . -175.70(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11362440
