Assembly of three pharmaceutical salts/cocrystals of tetrahydroberberine with sulfophenyl acids: improving the properties by formation of charge-assisted hydrogen bonds
Liu, Lixin; Zou, Dongyu; Zhang, Yunan; Zhang, Dajun; Zhang, Yu; Zhang, Qiang; Wang, Jian; Zeng, Shaoyu; Wang, Conggang; New Journal of Chemistry 43 (2019) 4886–; doi:10.1039/C9NJ00131J

data_7058204
_publ_section_title
;
 Assembly of three pharmaceutical salts/cocrystals of tetrahydroberberine
 with sulfophenyl acids: improving the properties by formation of
 charge-assisted hydrogen bonds
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4886
_journal_paper_doi               10.1039/C9NJ00131J
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C7 H7 O3 S, C20 H22 N O4, 1(C H4 O)'
_chemical_formula_sum            'C28 H33 N O8 S'
_chemical_formula_weight         543.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-11-07
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_audit_update_record
;
2018-12-05 deposited with the CCDC.    2019-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                68.593(7)
_cell_angle_beta                 83.020(6)
_cell_angle_gamma                74.648(7)
_cell_formula_units_Z            2
_cell_length_a                   8.2161(5)
_cell_length_b                   11.8768(11)
_cell_length_c                   15.3082(11)
_cell_measurement_reflns_used    6458
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.06
_cell_volume                     1340.59(19)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11366
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.264
_diffrn_reflns_theta_min         3.468
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48219
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         6102
_refine_ls_number_restraints     99
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0601
_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^)+(0.0839P)^2^+0.2444P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4024
_reflns_number_total             6102
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj00131j2.cif
_cod_data_source_block           zdy3
_cod_depositor_comments
'Adding full bibliography for 7058202--7058204.cif.'
_cod_database_code               7058204
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.930
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O10-C29 = C30-O9
 1.5 with sigma of 0.005
 O8-C28
 1.5 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
C30 \\sim O9 \\sim O10 \\sim C29 \\sim C28 \\sim O8: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(O9) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C30) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(O10) \\sim Ueq, Uanis(O9)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O8) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(O9)
\\sim Ueq, Uanis(O10) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: C30(0.33333) H30A(0.33333) H30B(0.33333) H30C(0.33333) O9(0.33333)
 H9(0.33333) O10(0.33333) H10(0.33333) C29(0.33333) H29A(0.33333) H29B(0.33333)
 H29C(0.33333) C28(0.33333) H28A(0.33333) H28B(0.33333) H28C(0.33333)
 O8(0.33333) H8(0.33333)
 Fixed X: C30(0.5748) O9(0.60044) O10(0.626161) C29(0.483469) C28(0.45585)
 O8(0.512589)
 Fixed Y: C30(0.463981) O9(0.338861) O10(0.518391) C29(0.53368) C28(0.44716)
 O8(0.321051)
 Fixed Z: C30(0.531469) O9(0.5334) O10(0.54817) C29(0.4987) C28(0.494529)
 O8(0.55708)
5.a Riding coordinates:
 C30(H30A,H30B,H30C), O9(H9), O10(H10), C29(H29A,H29B,H29C), C28(H28A,H28B,
 H28C), O8(H8)
5.b Ternary CH refined with riding coordinates:
 N1(H1), C5(H5)
5.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C0AA(H0AA,H0AB), C13(H13A,H13B), C17(H17A,H17B), C25(H25A,H25B)
5.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C14(H14), C16(H16), C18(H18), C19(H19), C22(H22), C24(H24)
5.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'