#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/13/2231372.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_2231372
loop_
_publ_author_name
'Burrow, Robert A.'
'Siqueira da Silva, Rubia M.'
_publ_section_title
;
 Methyl(phenyl)phosphinic acid
;
_journal_coeditor_code           ZB2012
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2005
_journal_paper_doi               10.1107/S1600536811025530
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C7 H9 O2 P'
_chemical_formula_moiety         'C7 H9 O2 P'
_chemical_formula_sum            'C7 H9 O2 P'
_chemical_formula_weight         156.11
_chemical_melting_point_gt       402
_chemical_melting_point_lt       408
_chemical_name_systematic
;
Methyl(phenyl)phosphinic acid
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2009.11-0'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.4231(8)
_cell_length_b                   7.8464(5)
_cell_length_c                   15.9801(10)
_cell_measurement_reflns_used    788
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      22.6780
_cell_measurement_theta_min      2.5292
_cell_volume                     1557.69(17)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker X8 Kappa APEXII'
_diffrn_measurement_method       '0.5° φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus ceramic X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19802
_diffrn_reflns_theta_full        30.49
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   '(SADABS; Bruker 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.394
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         2342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0521
_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)+(0.0622P)²+0.8980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1449
_reflns_number_gt                1506
_reflns_number_total             2342
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zb2012.cif
_cod_data_source_block           I
_cod_database_code               2231372
_cod_database_fobs_code          2231372
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
P P1 0.82414(4) 0.86402(6) 0.46093(3) 0.03532(18) Uani d . 1
O O1 0.85676(12) 1.0170(2) 0.51708(10) 0.0413(4) Uani d . 1
H H1 0.823(2) 1.114(4) 0.504(2) 0.062 Uiso d . 1
O O2 0.71118(12) 0.8030(2) 0.47403(10) 0.0456(4) Uani d . 1
C C1 0.9197(2) 0.7033(2) 0.48579(17) 0.0505(5) Uani d . 1
H H1A 0.9154 0.6771 0.5444 0.076 Uiso calc R 1
H H1B 0.9907 0.7433 0.4727 0.076 Uiso calc R 1
H H1C 0.9044 0.6026 0.4537 0.076 Uiso calc R 1
C C11 0.84247(18) 0.9303(2) 0.35447(12) 0.0384(5) Uani d . 1
C C12 0.9378(2) 1.0107(2) 0.32936(16) 0.0503(5) Uani d . 1
H H12 0.9933 1.0267 0.3676 0.06 Uiso calc R 1
C C13 0.9496(2) 1.0661(4) 0.24804(17) 0.0626(7) Uani d . 1
H H13 1.0128 1.1201 0.2317 0.075 Uiso calc R 1
C C14 0.8681(2) 1.0420(4) 0.19095(17) 0.0684(8) Uani d . 1
H H14 0.8762 1.0804 0.1363 0.082 Uiso calc R 1
C C15 0.7754(2) 0.9616(4) 0.21438(17) 0.0735(9) Uani d . 1
H H15 0.7211 0.9447 0.1752 0.088 Uiso calc R 1
C C16 0.7612(2) 0.9050(2) 0.29563(17) 0.0559(7) Uani d . 1
H H16 0.6977 0.8504 0.3109 0.067 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
P1 0.0314(2) 0.0321(2) 0.0425(2) -0.0001(2) 0.0008(2) 0.0015(2)
O1 0.0458(9) 0.0356(8) 0.0426(9) 0.0015(7) -0.0052(7) 0.0003(7)
O2 0.0328(8) 0.0381(8) 0.0660(11) -0.0008(7) 0.0059(7) 0.0031(7)
C1 0.0406(13) 0.0406(13) 0.0703(16) 0.0049(10) -0.0013(11) 0.0057(11)
C11 0.0404(11) 0.0356(11) 0.0391(11) -0.0005(9) -0.0005(9) -0.0028(9)
C12 0.0444(13) 0.0555(15) 0.0511(14) -0.0032(11) 0.0031(11) 0.0012(11)
C13 0.0661(18) 0.0662(17) 0.0555(16) -0.0018(15) 0.0193(14) 0.0039(14)
C14 0.100(3) 0.0658(18) 0.0395(14) 0.0060(18) 0.0101(15) 0.0029(13)
C15 0.095(2) 0.078(2) 0.0473(16) -0.007(2) -0.0204(15) -0.0019(15)
C16 0.0537(16) 0.0614(16) 0.0525(14) -0.0097(13) -0.0108(11) -0.0034(11)
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
O2 P1 O1 114.29(9)
O2 P1 C1 111.56(10)
O1 P1 C1 104.21(11)
O2 P1 C11 110.13(10)
O1 P1 C11 106.92(10)
C1 P1 C11 109.45(11)
P1 O1 H1 114.(2)
P1 C1 H1A 109.5
P1 C1 H1B 109.5
H1A C1 H1B 109.5
P1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C16 C11 C12 118.9(2)
C16 C11 P1 120.4(2)
C12 C11 P1 120.63(17)
C13 C12 C11 120.1(2)
C13 C12 H12 119.9
C11 C12 H12 119.9
C14 C13 C12 120.3(3)
C14 C13 H13 119.9
C12 C13 H13 119.9
C15 C14 C13 120.1(3)
C15 C14 H14 119.9
C13 C14 H14 119.9
C14 C15 C16 120.9(3)
C14 C15 H15 119.6
C16 C15 H15 119.6
C15 C16 C11 119.7(3)
C15 C16 H16 120.2
C11 C16 H16 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O2 1.4976(16)
P1 O1 1.5526(16)
P1 C1 1.777(2)
P1 C11 1.794(2)
O1 H1 0.89(3)
C1 H1A 0.96
C1 H1B 0.96
C1 H1C 0.96
C11 C16 1.394(3)
C11 C12 1.401(3)
C12 C13 1.378(4)
C12 H12 0.93
C13 C14 1.375(4)
C13 H13 0.93
C14 C15 1.366(5)
C14 H14 0.93
C15 C16 1.383(4)
C15 H15 0.93
C16 H16 0.93
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 H1 O2 6_765 0.89(3) 1.62(3) 2.494(2) 168(3) y
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
O2 P1 C11 C16 -6.3(2)
O1 P1 C11 C16 -131.0(2)
C1 P1 C11 C16 116.7(2)
O2 P1 C11 C12 172.62(18)
O1 P1 C11 C12 47.9(2)
C1 P1 C11 C12 -64.4(2)
C16 C11 C12 C13 1.1(4)
P1 C11 C12 C13 -177.8(2)
C11 C12 C13 C14 -0.4(4)
C12 C13 C14 C15 -0.5(5)
C13 C14 C15 C16 0.7(5)
C14 C15 C16 C11 0.0(5)
C12 C11 C16 C15 -0.9(4)
P1 C11 C16 C15 178.0(2)
