Hybrid interaction network of guanidinium-biphenyldisulfonic acid for the structure determination of liquid molecules
Qin, Shu-Qin; Gan, Qian-Ying; Xu, Wei; Jiang, Ren-Wang; CrystEngComm  (2022) –; doi:10.1039/D2CE00228K

data_7244808
_publ_section_title
;
 Hybrid interaction network of guanidinium-biphenyldisulfonic acid for the
 structure determination of liquid molecules
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00228K
_journal_year                    2022
_chemical_absolute_configuration -0.003(12)
_chemical_formula_moiety         'C12 H8 O6 S2, 2(C12 H22 O2), 2(C H6 N3)'
_chemical_formula_sum            'C38 H64 N6 O10 S2'
_chemical_formula_weight         829.06
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-21
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4527(2)
_cell_length_b                   13.4693(3)
_cell_length_c                   26.9148(5)
_cell_measurement_reflns_used    15446
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.6310
_cell_measurement_theta_min      3.6480
_cell_volume                     4514.40(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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      1.00  67.00   1.00    2.00    --   41.11 -99.00  30.00   66
  2  \w     23.00  65.00   1.00    2.00    --   41.11-125.00 -30.00   42
  3  \w     35.00 110.00   1.00    3.00    --  107.58 -61.00 -30.00   75
  4  \w     74.00 100.00   1.00    3.00    --  107.58 -94.00 -60.00   26
  5  \w     74.00 122.00   1.00    3.00    --  107.58-125.00-120.00   48
  6  \w     47.00 130.00   1.00    3.00    --  107.58 -61.00-150.00   83
  7  \w     80.00 177.00   1.00    3.00    --  107.58  30.00 -60.00   97
  8  \w    133.00 173.00   1.00    3.00    --  107.58  45.00-150.00   40
  9  \w    101.00 171.00   1.00    3.00    --  107.58 125.00-150.00   70
 10  \w     91.00 119.00   1.00    3.00    --  107.58  45.00-150.00   28
 11  \w     36.00 128.00   1.00    3.00    --  107.58 -15.00 -90.00   92
 12  \w     85.00 119.00   1.00    3.00    --  107.58-125.00  60.00   34
 13  \w     67.00 108.00   1.00    3.00    --  107.58 -94.00 120.00   41
 14  \w     53.00 132.00   1.00    3.00    --  107.58 -45.00 120.00   79
 15  \w     58.00  97.00   1.00    2.00    --   41.11-125.00 120.00   39
 16  \w     38.00  84.00   1.00    3.00    --  107.58 -45.00  60.00   46
 17  \w     25.00  61.00   1.00    3.00    --  107.58 -94.00-180.00   36
 18  \w    -36.00  -8.00   1.00    2.00    --  -41.11 125.00-150.00   28
 19  \w    -90.00 -54.00   1.00    2.00    --  -41.11 125.00-150.00   36
 20  \w   -114.00 -17.00   1.00    2.00    --  -41.11 -38.00  60.00   97
 21  \w   -118.00  -4.00   1.00    2.00    --  -41.11 -19.00 120.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0782330000
_diffrn_orient_matrix_UB_12      0.0551196000
_diffrn_orient_matrix_UB_13      -0.0347160000
_diffrn_orient_matrix_UB_21      0.0273452000
_diffrn_orient_matrix_UB_22      -0.0986796000
_diffrn_orient_matrix_UB_23      -0.0260553000
_diffrn_orient_matrix_UB_31      -0.0917675000
_diffrn_orient_matrix_UB_32      0.0174025000
_diffrn_orient_matrix_UB_33      -0.0373710000
_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  0.0442
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            32043
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.834
_diffrn_reflns_theta_min         3.284
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             1784
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 3355 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         8998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+1.1082P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1139
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                8307
_reflns_number_total             8998
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00228k3.cif
_cod_data_source_block           ysbhz_2
_cod_depositor_comments
;

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C19 H32 N3 O5 S'
_cod_original_formula_weight         414.53
_cod_original_formula_moiety         '0.5(C12 H8 O6 S2), C12 H22 O2, C H6 N3'
_cod_original_formula_units_Z            8
_cod_database_code               7244808
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3A(H3A), C6A(H6A), C1A(H1A), C10A(H10A), C6B(H6B), C3B(H3B), C10B(H10B),
 C1B(H1B)
2.b Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C5A(H5AA,H5AB), C2A(H2AA,H2AB), C5B(H5BA,H5BB), C4B(H4BA,
 H4BB), C2B(H2BA,H2BB)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
2.d X=CH2 refined with riding coordinates:
 N1(H1C,H1D), N2(H2A,H2B), N3(H3C,H3D), N4(H4A,H4B), N5(H5A,H5B), N6(H6C,H6D)
2.e Idealised Me refined as rotating group:
 C9A(H9AA,H9AB,H9AC), C11A(H11A,H11B,H11C), C12A(H12A,H12B,H12C), C8A(H8AA,
 H8AB,H8AC), C9B(H9BA,H9BB,H9BC), C11B(H11D,H11E,H11F), C12B(H12D,H12E,H12F),
 C8B(H8BA,H8BB,H8BC)
;
_shelx_res_checksum              56443
_shelx_hkl_checksum              29534
_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 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.583