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_7244606
_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         'C48 H40 O8 Sb4, 2(C H Cl3)'
_chemical_formula_sum            'C50 H42 Cl6 O8 Sb4'
_chemical_formula_weight         1470.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-16
_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                 112.5390(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.9804(2)
_cell_length_b                   13.64820(10)
_cell_length_c                   35.9388(3)
_cell_measurement_reflns_used    23941
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      68.0210
_cell_measurement_theta_min      2.6330
_cell_volume                     10410.92(17)
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (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(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_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    -57.00   3.00   0.50    0.50    --  -39.58 112.00-133.00  120
  2  \w      0.00  47.00   0.50    0.50    --   39.58-112.00 133.00   94
  3  \w    105.00 146.00   0.50    1.00    --   94.79 112.00-133.00   82
  4  \w     51.00 107.00   0.50    1.00    --   94.79-112.00 133.00  112
  5  \w    -74.00 -48.00   0.50    0.50    --  -39.58 138.00 150.00   52
  6  \w    -72.00 -28.00   0.50    0.50    --  -39.58 104.00 150.00   88
  7  \w   -103.00 -41.00   0.50    0.50    --  -39.58 -54.00 -30.00  124
  8  \w    -21.00  12.00   0.50    0.50    --  -39.58 104.00 150.00   66
  9  \w   -104.00 -68.00   0.50    0.50    --  -39.58 -43.00  90.00   72
 10  \w    -51.00 -26.00   0.50    0.50    --  -39.58 -43.00  90.00   50
 11  \w     18.00 104.00   0.50    0.50    --   39.58  65.00  30.00  172
 12  \w    -24.00   2.00   0.50    0.50    --   39.58 -32.00  60.00   52
 13  \w      0.00  50.00   0.50    0.50    --   39.58 -43.00-180.00  100
 14  \w     26.00  51.00   0.50    0.50    --   39.58 -32.00  60.00   50
 15  \w     -6.00  39.00   0.50    0.50    --   39.58 -32.00 120.00   90
 16  \w     29.00  56.00   0.50    1.00    --   94.79-117.00 -90.00   54
 17  \w    102.00 128.00   0.50    1.00    --   94.79  96.00 150.00   52
 18  \w     23.00 105.00   0.50    1.00    --   94.79 -96.00 150.00  164
 19  \w     22.00  64.00   0.50    1.00    --   94.79 -96.00  60.00   84
 20  \w     86.00 141.00   0.50    1.00    --   94.79  77.00 -90.00  110
 21  \w    120.00 146.00   0.50    1.00    --   94.79 117.00  30.00   52
 22  \w     35.00 117.00   0.50    1.00    --   94.79 -68.00 150.00  164
 23  \w     85.00 157.00   0.50    1.00    --   94.79  77.00  60.00  144
 24  \w     31.00 101.00   0.50    1.00    --   94.79 -50.00 150.00  140
 25  \w    103.00 147.00   0.50    1.00    --   94.79  77.00 -30.00   88
 26  \w     90.00 116.00   0.50    1.00    --   94.79  33.00 -30.00   52
 27  \w     77.00 103.00   0.50    1.00    --   94.79-117.00 -90.00   52
 28  \w     65.00  91.00   0.50    1.00    --   94.79 -68.00 120.00   52
 29  \w     82.00 155.00   0.50    1.00    --   94.79 117.00 150.00  146
 30  \w     86.00 156.00   0.50    1.00    --   94.79 117.00  90.00  140
 31  \w    -63.00 -38.00   0.50    0.50    --  -39.58 112.00-133.00   50
 32  \w   -107.00 -80.00   0.50    0.50    --  -39.58 -21.00 120.00   54
 33  \w    -66.00 -30.00   0.50    0.50    --  -39.58 -21.00 120.00   72
 34  \w   -104.00 -76.00   0.50    0.50    --  -39.58 -32.00-120.00   56
 35  \w    -24.00  21.00   0.50    0.50    --   39.58 -43.00 -60.00   90
 36  \w     30.00  65.00   0.50    0.50    --   39.58  32.00-120.00   70
 37  \w     34.00  61.00   0.50    0.50    --   39.58 -77.00 -30.00   54
 38  \w    -26.00   7.00   0.50    0.50    --   39.58 -77.00 -30.00   66
 39  \w     26.00  52.00   0.50    0.50    --   39.58 -43.00 -60.00   52
;
_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      -0.0099685000
_diffrn_orient_matrix_UB_12      0.1106835000
_diffrn_orient_matrix_UB_13      -0.0084333000
_diffrn_orient_matrix_UB_21      -0.0518257000
_diffrn_orient_matrix_UB_22      -0.0000108000
_diffrn_orient_matrix_UB_23      0.0173156000
_diffrn_orient_matrix_UB_31      0.0498559000
_diffrn_orient_matrix_UB_32      0.0221276000
_diffrn_orient_matrix_UB_33      0.0422140000
_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  0.0469
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            28825
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.112
_diffrn_reflns_theta_min         2.662
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    19.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.876
_exptl_crystal_description       prism
_exptl_crystal_F_000             5696
_exptl_crystal_recrystallization_method 'Solvent evaporation'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.516
_refine_diff_density_min         -1.438
_refine_diff_density_rms         0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     607
_refine_ls_number_reflns         9385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+31.2838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8936
_reflns_number_total             9385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cp00286h3.cif
_cod_data_source_block           1ver0-18009_art-017
_cod_original_cell_volume        10410.92(16)
_cod_database_code               7244606
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C48 H40 Sb4 O8'
_shelx_estimated_absorpt_t_max   0.304
_shelx_estimated_absorpt_t_min   0.099
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1) = Uanis(O2)
3.a Ternary CH refined with riding coordinates:
 C1B(H1B), C1A(H1A)
3.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C14(H14), C24(H24), C18(H18), C48(H48), C21(H21), C45(H45),
 C12(H12), C17(H17), C15(H15), C36(H36), C11(H11), C46(H46), C26(H26), C29(H29),
  C16(H16), C8(H8), C44(H44), C28(H28), C10(H10), C32(H32), C27(H27), C22(H22),
 C23(H23), C30(H30), C47(H47), C35(H35), C38(H38), C2(H2), C40(H40), C6(H6),
 C34(H34), C42(H42), C33(H33), C5(H5), C9(H9), C4(H4), C3(H3), C41(H41),
 C39(H39)
;
_shelx_res_checksum              11444
_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 2.641
_oxdiff_exptl_absorpt_empirical_full_min 0.598