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_7244800
_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         'C12 H8 O6 S2, C10 H11 O2, 2(C H6 N3)'
_chemical_formula_sum            'C24 H31 N6 O8 S2'
_chemical_formula_weight         595.67
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-14
_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                97.548(9)
_cell_angle_beta                 90.802(11)
_cell_angle_gamma                94.115(10)
_cell_formula_units_Z            1
_cell_length_a                   6.2266(9)
_cell_length_b                   7.1344(7)
_cell_length_c                   14.1593(15)
_cell_measurement_reflns_used    2138
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      28.6590
_cell_measurement_theta_min      2.8810
_cell_volume                     621.77(13)
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.988
_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    -59.00  37.00   1.00    4.00    --   11.74 -57.00 -30.00   96
  2  \w    -16.00  79.00   1.00    4.00    --   11.74  77.00-120.00   95
  3  \w    -16.00  82.00   1.00    4.00    --   11.74  57.00 120.00   98
;
_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      -0.1100039000
_diffrn_orient_matrix_UB_12      0.0103497000
_diffrn_orient_matrix_UB_13      0.0103010000
_diffrn_orient_matrix_UB_21      0.0188915000
_diffrn_orient_matrix_UB_22      -0.0207525000
_diffrn_orient_matrix_UB_23      0.0469113000
_diffrn_orient_matrix_UB_31      0.0243583000
_diffrn_orient_matrix_UB_32      0.0978552000
_diffrn_orient_matrix_UB_33      0.0157528000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2175
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.557
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52079
_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    1.591
_exptl_crystal_description       block
_exptl_crystal_F_000             313
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         2175
_refine_ls_number_restraints     337
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0789
_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^)+(0.1184P)^2^+1.0201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2101
_refine_ls_wR_factor_ref         0.2220
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1803
_reflns_number_total             2175
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00228k3.cif
_cod_data_source_block           c1bf4
_cod_database_code               7244800
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.939
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.673(12)
 0.327(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C5-O5 = O5-C10
 1.42 with sigma of 0.02
 C4-O4
 1.32 with sigma of 0.02
 C8-C9
 1.52 with sigma of 0.02
 C2-C1
 1.39 with sigma of 0.02
 C1-C7
 1.52 with sigma of 0.02
 C7-C8
 1.32 with sigma of 0.02
 C2-C7
 2.521 with sigma of 0.04
 C9-C7
 2.462 with sigma of 0.04
 C1-C8
 2.462 with sigma of 0.04
 C14A-C13 \\sim C15A-C14A \\sim C16-C15A \\sim C11A-C16 \\sim C12A-C11A \\sim
C12A-C13
 with sigma of 0.02
 C14-C13 \\sim C15-C14 \\sim C16-C15 \\sim C11-C16 \\sim C12-C11 \\sim C12-C13
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
O4 \\sim O5 \\sim C1 \\sim C6 \\sim C5 \\sim C4 \\sim C3 \\sim C2 \\sim C7
\\sim C8 \\sim C9 \\sim C10: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
Uanis(C1) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim
Ueq, Uanis(C6) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C3)
\\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(O4) \\sim Ueq,
Uanis(C10) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
5. Rigid body (RIGU) restrains
 O4, O5, C1, C6, C5, C4, C3, C2, C7, C8, C9, C10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C11, C12, C13, C14, C15, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C11A, C12A, C13, C14A, C15A, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=1-FVAR(1)
 Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=FVAR(1)
 Fixed Sof: O4(0.5) O5(0.5) C1(0.5) C6(0.5) H6(0.5) C5(0.5) C4(0.5) C3(0.5)
 H3(0.5) C2(0.5) H2(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5) H9A(0.5)
 H9B(0.5) H9C(0.5) C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5)
7.a Riding coordinates:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
7.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C2(H2), C7(H7), C8(H8), C11(H11), C11A(H11A), C12(H12),
 C12A(H12A), C14(H14), C14A(H14A), C15(H15), C15A(H15A)
7.c Fitted hexagon refined as free rotating group:
 C1(C6,C5,C4,C3,C2)
7.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B)
;
_shelx_res_checksum              60700
_shelx_hkl_checksum              98559
_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 1.712
_oxdiff_exptl_absorpt_empirical_full_min 0.614