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_7244602
_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 O2 P'
_chemical_formula_sum            'C12 H11 O2 P'
_chemical_formula_weight         218.18
_chemical_name_systematic        'Diphenylphosphinic 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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-10-08 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.199(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4435(3)
_cell_length_b                   5.9428(2)
_cell_length_c                   15.6087(4)
_cell_measurement_reflns_used    3329
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      68.1050
_cell_measurement_theta_min      3.8730
_cell_volume                     1044.72(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_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      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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   -100.00 -43.00   0.50    0.60    --  -39.58 -37.00  82.00  114
  2  \w    -21.00   6.00   0.50    0.60    --  -39.58  37.00-121.00   54
  3  \w    -16.00  15.00   0.50    0.60    --   39.58 -37.00  82.00   62
  4  \w     36.00  80.00   0.50    0.60    --   39.58  37.00-121.00   88
  5  \w     32.00 108.00   0.50    3.00    --   94.79 -37.00  82.00  152
  6  \w    106.00 157.00   0.50    3.00    --   94.79  37.00-121.00  102
  7  \w    -56.00  12.00   0.50    0.60    --  -39.58 104.00 -90.00  136
  8  \w    -62.00 -23.00   0.50    0.60    --  -39.58 -65.00   0.00   78
  9  \w   -101.00 -55.00   0.50    0.60    --  -39.58 -43.00 -30.00   92
 10  \w    -52.00 -26.00   0.50    0.60    --  -39.58 -43.00 -30.00   52
 11  \w    -47.00 -22.00   0.50    0.60    --  -39.58 -65.00 -90.00   50
 12  \w   -101.00 -64.00   0.50    0.60    --  -39.58 -65.00 -90.00   74
 13  \w     -4.00  21.00   0.50    0.60    --   39.58 -32.00  90.00   50
 14  \w     39.00  80.00   0.50    0.60    --   39.58  32.00-150.00   82
 15  \w     25.00  50.00   0.50    0.60    --   39.58 -32.00  90.00   50
 16  \w     30.00  96.00   0.50    3.00    --   94.79 -25.00-120.00  132
 17  \w     84.00 139.00   0.50    3.00    --   94.79  77.00   0.00  110
 18  \w     29.00  79.00   0.50    3.00    --   94.79 -96.00 -90.00  100
 19  \w     84.00 154.00   0.50    3.00    --   94.79  25.00-180.00  140
 20  \w     68.00  97.00   0.50    3.00    --   94.79 145.00  30.00   58
 21  \w    103.00 157.00   0.50    3.00    --   94.79  42.00-150.00  108
 22  \w     78.00 106.00   0.50    3.00    --   94.79 -33.00   0.00   56
 23  \w    130.00 156.00   0.50    3.00    --   94.79 145.00  30.00   52
 24  \w     56.00 120.00   0.50    3.00    --   94.79 -77.00 -60.00  128
 25  \w     34.00  68.00   0.50    3.00    --   94.79 -33.00   0.00   68
 26  \w    124.00 150.00   0.50    3.00    --   94.79 117.00 120.00   52
 27  \w     58.00 155.00   0.50    3.00    --   94.79   8.00   0.00  194
 28  \w     35.00  96.00   0.50    3.00    --   94.79 -42.00-120.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0956330000
_diffrn_orient_matrix_UB_12      0.1151537000
_diffrn_orient_matrix_UB_13      0.0677457000
_diffrn_orient_matrix_UB_21      0.0925260000
_diffrn_orient_matrix_UB_22      -0.0397598000
_diffrn_orient_matrix_UB_23      -0.0591324000
_diffrn_orient_matrix_UB_31      -0.0322067000
_diffrn_orient_matrix_UB_32      0.2286325000
_diffrn_orient_matrix_UB_33      -0.0443490000
_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  0.0264
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4553
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.475
_diffrn_reflns_theta_max         67.475
_diffrn_reflns_theta_min         3.925
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_recrystallization_method 'Solvent evaporation'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0453P)^2^+0.5341P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1668
_reflns_number_total             1876
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cp00286h3.cif
_cod_data_source_block           0ver0-18204_fcn-001new
_cod_database_code               7244602
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C12 H11 O4 P1'
_shelx_estimated_absorpt_t_max   0.919
_shelx_estimated_absorpt_t_min   0.815
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C6(H6), C2(H2), C10(H10), C11(H11), C4(H4), C8(H8), C3(H3), C9(H9),
 C5(H5)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              14200
_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 1.484
_oxdiff_exptl_absorpt_empirical_full_min 0.829