#------------------------------------------------------------------------------
#$Date: 2022-03-16 03:48:36 +0200 (Wed, 16 Mar 2022) $
#$Revision: 273714 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/46/7244601.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7244601
loop_
_publ_author_name
'Yakubenko, Artyom A.'
'Puzyk, Aleksandra M.'
'Korostelev, Vladislav O.'
'Mulloyarova, Valeriia V.'
'Tupikina, Elena Yu.'
'Tolstoy, Peter'
'Antonov, Alexander S.'
_publ_section_title
;
 Self-association of diphenylpnictoginic acids in solution and solid
 state: covalent vs hydrogen bonding
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D2CP00286H
_journal_year                    2022
_chemical_formula_moiety         'C12 H11 As O2'
_chemical_formula_sum            'C12 H11 As O2'
_chemical_formula_weight         262.13
_chemical_name_systematic        'Diphenylarsinic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-10-08 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.389(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4506(4)
_cell_length_b                   6.0251(2)
_cell_length_c                   15.7851(4)
_cell_measurement_reflns_used    6724
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.5610
_cell_measurement_theta_min      3.9100
_cell_volume                     1074.44(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  42.00   0.50    0.15    --   47.20 -37.00  90.00  134
  2  ω     95.00 132.00   0.50    0.50    --  107.75  45.00  30.00   74
  3  ω    146.00 172.00   0.50    0.50    --  107.75  45.00  30.00   52
  4  ω    136.00 174.00   0.50    0.50    --  107.75  45.00 -30.00   76
  5  ω    106.00 131.00   0.50    0.50    --  107.75 107.00 -59.00   50
  6  ω     99.00 127.00   0.50    0.50    --  107.75  45.00 -30.00   56
  7  ω    112.00 177.00   0.50    0.50    --  107.75  45.00 -90.00  130
  8  ω     84.00 116.00   0.50    0.15    --   47.20 125.00 -90.00   64
  9  ω     79.00 104.00   0.50    0.15    --   47.20 125.00-120.00   50
 10  ω     74.00 116.00   0.50    0.15    --   47.20 125.00-150.00   84
 11  ω     35.00  63.00   0.50    0.50    --  107.75 -61.00-150.00   56
 12  ω     78.00 104.00   0.50    0.50    --  107.75 -94.00-150.00   52
 13  ω     42.00  68.00   0.50    0.50    --  107.75-107.00-157.00   52
 14  ω     42.00 111.00   0.50    0.50    --  107.75-125.00-150.00  138
 15  ω     35.00  75.00   0.50    0.50    --  107.75 -94.00-150.00   80
 16  ω     21.00  50.00   0.50    0.15    --   47.20-107.00-157.00   58
 17  ω     36.00  62.00   0.50    0.50    --  107.75 -61.00  30.00   52
 18  ω    -84.00  -2.00   0.50    0.15    --  -47.20 107.00 -59.00  164
 19  ω   -106.00 -54.00   0.50    0.50    -- -106.00 107.00 -59.00  104
 20  ω    -71.00 -33.00   0.50    0.50    -- -106.00  61.00 -30.00   76
 21  ω    -71.00 -34.00   0.50    0.50    -- -106.00  61.00 -60.00   74
 22  ω    -61.00 -36.00   0.50    0.50    -- -106.00  77.00  60.00   50
 23  ω    -63.00 -37.00   0.50    0.50    -- -106.00  61.00 120.00   52
 24  ω   -132.00 -94.00   0.50    0.50    -- -106.00 -61.00  60.00   76
 25  ω   -172.00-147.00   0.50    0.50    -- -106.00 -61.00  60.00   50
 26  ω   -148.00-114.00   0.50    0.50    -- -106.00-107.00-157.00   68
 27  ω   -144.00 -93.00   0.50    0.50    -- -106.00 -30.00-150.00  102
 28  ω   -176.00-150.00   0.50    0.50    -- -106.00 -30.00-150.00   52
 29  ω   -104.00 -73.00   0.50    0.50    -- -106.00  77.00 -60.00   62
 30  ω   -111.00 -63.00   0.50    0.50    -- -106.00 125.00-120.00   96
 31  ω    137.00 163.00   0.50    0.50    --  107.75 107.00 -59.00   52
 32  ω    -26.00  23.00   0.50    0.15    --  -47.20  19.00   0.00   98
 33  ω   -120.00 -55.00   0.50    0.15    --  -47.20 -37.00  90.00  130
 34  ω     -7.00  28.00   0.50    0.15    --  -47.20  19.00 -90.00   70
 35  ω   -112.00 -87.00   0.50    0.50    -- -106.00 125.00 -60.00   50
 36  ω    -60.00 -34.00   0.50    0.50    -- -106.00  77.00 -90.00   52
 37  ω    -64.00 -38.00   0.50    0.50    -- -106.00  61.00 -90.00   52
 38  ω    -60.00 -34.00   0.50    0.50    -- -106.00  61.00-120.00   52
 39  ω   -109.00 -84.00   0.50    0.50    -- -106.00 117.00 -31.14   50
 40  ω   -168.00-136.00   0.50    0.50    -- -106.00 -61.00 120.00   64
 41  ω    -58.00 -33.00   0.50    0.50    -- -106.00 125.00   0.00   50
 42  ω    -63.00 -37.00   0.50    0.50    -- -106.00 117.00  79.60   52
 43  ω   -108.00 -83.00   0.50    0.50    -- -106.00 109.00  78.19   50
 44  ω   -175.00-140.00   0.50    0.50    -- -106.00 -15.00  90.00   70
 45  ω   -109.00 -70.00   0.50    0.50    -- -106.00 117.00  79.60   78
 46  ω    110.00 139.00   0.50    0.50    --  107.75  45.00 120.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1279188000
_diffrn_orient_matrix_UB_12      0.0789704000
_diffrn_orient_matrix_UB_13      -0.0002409000
_diffrn_orient_matrix_UB_21      -0.0458745000
_diffrn_orient_matrix_UB_22      0.2353743000
_diffrn_orient_matrix_UB_23      -0.0245666000
_diffrn_orient_matrix_UB_31      0.0114673000
_diffrn_orient_matrix_UB_32      0.0608776000
_diffrn_orient_matrix_UB_33      0.0958322000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11076
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.250
_diffrn_reflns_theta_min         3.913
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method 'Solvent evaporation'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.185
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0275
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0342P)²+0.7458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0750
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2067
_reflns_number_total             2220
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cp00286h3.cif
_cod_data_source_block           ver0-17146_art-003
_cod_database_code               7244601
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C12 H11 As1 O2'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C4(H4), C12(H12), C8(H8), C11(H11), C3(H3), C10(H10),
 C9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.771
_oxdiff_exptl_absorpt_empirical_full_min 0.706
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
As1 As 0.16654(2) 0.60282(4) 0.75360(2) 0.01563(10) Uani 1 1 d . . . . .
O1 O 0.12887(16) 0.8772(3) 0.75555(10) 0.0220(3) Uani 1 1 d . . . . .
O2 O 0.08706(14) 0.4340(3) 0.80411(10) 0.0224(3) Uani 1 1 d . . . . .
C7 C 0.32703(19) 0.6118(3) 0.81040(13) 0.0183(4) Uani 1 1 d . . . . .
C2 C 0.1992(2) 0.6838(4) 0.58157(14) 0.0235(4) Uani 1 1 d . . . . .
H2 H 0.2268 0.8211 0.6031 0.028 Uiso 1 1 calc R U . . .
C5 C 0.1161(2) 0.2738(4) 0.51710(15) 0.0245(5) Uani 1 1 d . . . . .
H5 H 0.0885 0.1368 0.4953 0.029 Uiso 1 1 calc R U . . .
C1 C 0.16030(18) 0.5258(4) 0.63533(13) 0.0182(4) Uani 1 1 d . . . . .
C6 C 0.1187(2) 0.3207(4) 0.60393(14) 0.0225(4) Uani 1 1 d . . . . .
H6 H 0.0930 0.2162 0.6401 0.027 Uiso 1 1 calc R U . . .
C4 C 0.1541(2) 0.4291(4) 0.46333(14) 0.0247(5) Uani 1 1 d . . . . .
H4 H 0.1516 0.3967 0.4055 0.030 Uiso 1 1 calc R U . . .
C12 C 0.3937(2) 0.8024(4) 0.80465(14) 0.0237(4) Uani 1 1 d . . . . .
H12 H 0.3604 0.9245 0.7737 0.028 Uiso 1 1 calc R U . . .
C8 C 0.3757(2) 0.4279(4) 0.85592(14) 0.0226(4) Uani 1 1 d . . . . .
H8 H 0.3307 0.3006 0.8591 0.027 Uiso 1 1 calc R U . . .
C11 C 0.5106(2) 0.8081(5) 0.84578(16) 0.0305(5) Uani 1 1 d . . . . .
H11 H 0.5561 0.9346 0.8422 0.037 Uiso 1 1 calc R U . . .
C3 C 0.1960(2) 0.6330(4) 0.49533(15) 0.0276(5) Uani 1 1 d . . . . .
H3 H 0.2222 0.7365 0.4590 0.033 Uiso 1 1 calc R U . . .
C10 C 0.5593(2) 0.6262(5) 0.89195(16) 0.0310(6) Uani 1 1 d . . . . .
H10 H 0.6373 0.6313 0.9200 0.037 Uiso 1 1 calc R U . . .
C9 C 0.4926(2) 0.4366(5) 0.89661(16) 0.0300(5) Uani 1 1 d . . . . .
H9 H 0.5263 0.3142 0.9272 0.036 Uiso 1 1 calc R U . . .
H1 H 0.060(4) 0.893(6) 0.736(3) 0.049(11) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
As As -0.9300 1.0051 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 As1 C7 100.97(9) . . ?
O1 As1 C1 106.42(9) . . ?
O2 As1 O1 115.19(8) . . ?
O2 As1 C7 110.75(9) . . ?
O2 As1 C1 112.65(9) . . ?
C7 As1 C1 110.18(9) . . ?
As1 O1 H1 110(3) . . ?
C12 C7 As1 119.31(17) . . ?
C8 C7 As1 119.68(17) . . ?
C8 C7 C12 121.0(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C3 C2 C1 119.0(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(2) . . ?
C2 C1 As1 117.58(16) . . ?
C6 C1 As1 121.39(16) . . ?
C6 C1 C2 121.0(2) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 C5 118.9(2) . . ?
C1 C6 H6 120.6 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C7 C12 H12 120.4 . . ?
C7 C12 C11 119.2(2) . . ?
C11 C12 H12 120.4 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.0(2) . . ?
C9 C8 H8 120.5 . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H11 119.9 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C11 C10 H10 119.9 . . ?
C11 C10 C9 120.3(2) . . ?
C9 C10 H10 119.9 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
As1 O1 1.7101(16) . ?
As1 O2 1.6541(15) . ?
As1 C7 1.910(2) . ?
As1 C1 1.914(2) . ?
O1 H1 0.81(4) . ?
C7 C12 1.390(3) . ?
C7 C8 1.387(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.395(3) . ?
C2 C3 1.390(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(3) . ?
C5 C4 1.380(4) . ?
C1 C6 1.386(3) . ?
C6 H6 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.384(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.390(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.382(4) . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.383(4) . ?
C9 H9 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
As1 C7 C12 C11 -179.74(17) . . . . ?
As1 C7 C8 C9 179.77(17) . . . . ?
As1 C1 C6 C5 179.94(17) . . . . ?
C7 C12 C11 C10 -0.2(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C5 C4 C3 C2 -0.6(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C6 C5 C4 C3 0.4(4) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C12 C7 C8 C9 0.5(3) . . . . ?
C12 C11 C10 C9 0.8(4) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
C11 C10 C9 C8 -0.8(4) . . . . ?
C3 C2 C1 As1 179.87(18) . . . . ?
C3 C2 C1 C6 -0.1(3) . . . . ?
