Self-association of diphenylpnictoginic acids in solution and solid state: covalent vs hydrogen bonding
Yakubenko, Artyom A.; Puzyk, Aleksandra M.; Korostelev, Vladislav O.; Mulloyarova, Valeriia V.; Tupikina, Elena Yu.; Tolstoy, Peter; Antonov, Alexander S.; Physical Chemistry Chemical Physics  (2022) –; doi:10.1039/D2CP00286H

data_7244601
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -25.00  42.00   0.50    0.15    --   47.20 -37.00  90.00  134
  2  \w     95.00 132.00   0.50    0.50    --  107.75  45.00  30.00   74
  3  \w    146.00 172.00   0.50    0.50    --  107.75  45.00  30.00   52
  4  \w    136.00 174.00   0.50    0.50    --  107.75  45.00 -30.00   76
  5  \w    106.00 131.00   0.50    0.50    --  107.75 107.00 -59.00   50
  6  \w     99.00 127.00   0.50    0.50    --  107.75  45.00 -30.00   56
  7  \w    112.00 177.00   0.50    0.50    --  107.75  45.00 -90.00  130
  8  \w     84.00 116.00   0.50    0.15    --   47.20 125.00 -90.00   64
  9  \w     79.00 104.00   0.50    0.15    --   47.20 125.00-120.00   50
 10  \w     74.00 116.00   0.50    0.15    --   47.20 125.00-150.00   84
 11  \w     35.00  63.00   0.50    0.50    --  107.75 -61.00-150.00   56
 12  \w     78.00 104.00   0.50    0.50    --  107.75 -94.00-150.00   52
 13  \w     42.00  68.00   0.50    0.50    --  107.75-107.00-157.00   52
 14  \w     42.00 111.00   0.50    0.50    --  107.75-125.00-150.00  138
 15  \w     35.00  75.00   0.50    0.50    --  107.75 -94.00-150.00   80
 16  \w     21.00  50.00   0.50    0.15    --   47.20-107.00-157.00   58
 17  \w     36.00  62.00   0.50    0.50    --  107.75 -61.00  30.00   52
 18  \w    -84.00  -2.00   0.50    0.15    --  -47.20 107.00 -59.00  164
 19  \w   -106.00 -54.00   0.50    0.50    -- -106.00 107.00 -59.00  104
 20  \w    -71.00 -33.00   0.50    0.50    -- -106.00  61.00 -30.00   76
 21  \w    -71.00 -34.00   0.50    0.50    -- -106.00  61.00 -60.00   74
 22  \w    -61.00 -36.00   0.50    0.50    -- -106.00  77.00  60.00   50
 23  \w    -63.00 -37.00   0.50    0.50    -- -106.00  61.00 120.00   52
 24  \w   -132.00 -94.00   0.50    0.50    -- -106.00 -61.00  60.00   76
 25  \w   -172.00-147.00   0.50    0.50    -- -106.00 -61.00  60.00   50
 26  \w   -148.00-114.00   0.50    0.50    -- -106.00-107.00-157.00   68
 27  \w   -144.00 -93.00   0.50    0.50    -- -106.00 -30.00-150.00  102
 28  \w   -176.00-150.00   0.50    0.50    -- -106.00 -30.00-150.00   52
 29  \w   -104.00 -73.00   0.50    0.50    -- -106.00  77.00 -60.00   62
 30  \w   -111.00 -63.00   0.50    0.50    -- -106.00 125.00-120.00   96
 31  \w    137.00 163.00   0.50    0.50    --  107.75 107.00 -59.00   52
 32  \w    -26.00  23.00   0.50    0.15    --  -47.20  19.00   0.00   98
 33  \w   -120.00 -55.00   0.50    0.15    --  -47.20 -37.00  90.00  130
 34  \w     -7.00  28.00   0.50    0.15    --  -47.20  19.00 -90.00   70
 35  \w   -112.00 -87.00   0.50    0.50    -- -106.00 125.00 -60.00   50
 36  \w    -60.00 -34.00   0.50    0.50    -- -106.00  77.00 -90.00   52
 37  \w    -64.00 -38.00   0.50    0.50    -- -106.00  61.00 -90.00   52
 38  \w    -60.00 -34.00   0.50    0.50    -- -106.00  61.00-120.00   52
 39  \w   -109.00 -84.00   0.50    0.50    -- -106.00 117.00 -31.14   50
 40  \w   -168.00-136.00   0.50    0.50    -- -106.00 -61.00 120.00   64
 41  \w    -58.00 -33.00   0.50    0.50    -- -106.00 125.00   0.00   50
 42  \w    -63.00 -37.00   0.50    0.50    -- -106.00 117.00  79.60   52
 43  \w   -108.00 -83.00   0.50    0.50    -- -106.00 109.00  78.19   50
 44  \w   -175.00-140.00   0.50    0.50    -- -106.00 -15.00  90.00   70
 45  \w   -109.00 -70.00   0.50    0.50    -- -106.00 117.00  79.60   78
 46  \w    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       '\w 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/[\s^2^(Fo^2^)+(0.0342P)^2^+0.7458P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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'
_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)
;
_shelx_res_checksum              19423
_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