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_7244803
_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_formula_moiety         '2(C6 H4 O3 S), C10 H18 O, 2(C H6 N3)'
_chemical_formula_sum            'C24 H39 N6 O7 S2'
_chemical_formula_weight         587.73
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-12-13
_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                   39.275(9)
_cell_length_b                   12.1367(13)
_cell_length_c                   7.3230(9)
_cell_measurement_reflns_used    1287
_cell_measurement_temperature    99.97(14)
_cell_measurement_theta_max      62.5290
_cell_measurement_theta_min      3.7770
_cell_volume                     3490.6(10)
_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      99.97(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.955
_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    -21.00  69.00   1.00    8.00    --   40.73 -57.00  30.00   90
  2  \w     29.00  82.00   1.00    8.00    --   40.73 -99.00 -30.00   53
  3  \w     76.00 127.00   1.00   10.00    --  107.58 -45.00   0.00   51
  4  \w     79.00 158.00   1.00   10.00    --  107.58  30.00-120.00   79
  5  \w     37.00 111.00   1.00   10.00    --  107.58-125.00 -60.00   74
  6  \w    111.00 176.00   1.00   10.00    --  107.58  45.00 150.00   65
  7  \w    -74.00 -40.00   1.00    8.00    --  -40.73 125.00 120.00   34
;
_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      -0.1879210000
_diffrn_orient_matrix_UB_12      -0.0115214000
_diffrn_orient_matrix_UB_13      0.0431439000
_diffrn_orient_matrix_UB_21      -0.0417272000
_diffrn_orient_matrix_UB_22      0.0367358000
_diffrn_orient_matrix_UB_23      0.0366782000
_diffrn_orient_matrix_UB_31      -0.0849510000
_diffrn_orient_matrix_UB_32      0.0074606000
_diffrn_orient_matrix_UB_33      -0.1135997000
_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  0.0639
_diffrn_reflns_av_unetI/netI     0.1166
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8655
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.356
_diffrn_reflns_theta_min         3.812
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.752
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72671
_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    1.118
_exptl_crystal_description       block
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.142
_refine_ls_abs_structure_details
;
 Flack x determined using 828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         6067
_refine_ls_number_restraints     88
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1755
_refine_ls_R_factor_gt           0.1514
_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^)+(0.1680P)^2^+26.7792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3810
_refine_ls_wR_factor_ref         0.4012
_reflns_Friedel_coverage         0.559
_reflns_Friedel_fraction_full    0.779
_reflns_Friedel_fraction_max     0.712
_reflns_number_gt                4200
_reflns_number_total             6067
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00228k3.cif
_cod_data_source_block           1-l_3_sq
_cod_original_cell_volume        3490.7(10)
_cod_database_code               7244803
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.78
_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, All O(H) groups
2. Rigid bond restraints
 C19, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C23, C22
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C7, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 S1, O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C23 \\sim C22: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C7 \\sim C8: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C19 \\sim C20: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
S1 \\sim O2: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
Uanis(C19) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C16)
\\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C11) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C3) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C21) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(O4) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(N4) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C15) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
4.a Rotating group:
 N5(H5C,H5D)
4.b Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C1(H1)
4.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
4.d Aromatic/amide H refined with riding coordinates:
 C24(H24), C23(H23), C21(H21), C20(H20), C15(H15), C14(H14), C18(H18), C17(H17)
4.e X=CH2 refined with riding coordinates:
 C8(H8A,H8B), N1(H1A,H1B), N2(H2A,H2B), N3(H3C,H3D), N4(H4A,H4B), N6(H6C,H6D)
4.f Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
4.g Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_shelx_res_checksum              53835
_shelx_hkl_checksum              12070
_shelx_fab_checksum              16520
_platon_squeeze_void_probe_radius 1.20
_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 1.335
_oxdiff_exptl_absorpt_empirical_full_min 0.760