Four solid forms of tauroursodeoxycholic acid and solid-state transformations: effects of temperature and milling
Xu, Kailin; Zheng, Shoujun; Guo, Liuqi; Li, Shanshan; Wang, Lili; Tang, Peixiao; Yan, Jin; Wu, Di; Li, Hui; RSC Adv.  (2015) –; doi:10.1039/C5RA18985C

data_7223092
_publ_section_title
;
 Four solid forms of tauroursodeoxycholic acid and solid-state
 transformations: effects of temperature and milling
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA18985C
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C26 H44 N O6 S, H3 O, H2 O'
_chemical_formula_sum            'C26 H49 N O8 S'
_chemical_formula_weight         535.72
_chemical_name_systematic        'tauroursodeoxycholic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2015-09-17 deposited with the CCDC.
2015-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.145(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6537(4)
_cell_length_b                   8.3429(3)
_cell_length_c                   17.2850(7)
_cell_measurement_reflns_used    1985
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6530
_cell_measurement_theta_min      3.3860
_cell_volume                     1391.85(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   40.00   66.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361  178.0000   90.0000 26

  2 omega   -6.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361   38.0000  -30.0000 76

  3 omega   -6.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361   38.0000 -120.0000 98

  4 omega  -39.00  -10.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174   57.0000 -150.0000 29
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0561367000
_diffrn_orient_matrix_UB_12      -0.0341214000
_diffrn_orient_matrix_UB_13      -0.0213578000
_diffrn_orient_matrix_UB_21      -0.0426937000
_diffrn_orient_matrix_UB_22      0.0074200000
_diffrn_orient_matrix_UB_23      0.0327249000
_diffrn_orient_matrix_UB_31      -0.0206617000
_diffrn_orient_matrix_UB_32      0.0775232000
_diffrn_orient_matrix_UB_33      -0.0125370000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6228
_diffrn_reflns_point_group_measured_fraction_full 0.800
_diffrn_reflns_point_group_measured_fraction_max 0.789
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.133
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'white translucent'
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1056 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4487
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0413P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0938
_reflns_Friedel_coverage         0.476
_reflns_Friedel_fraction_full    0.571
_reflns_Friedel_fraction_max     0.548
_reflns_number_gt                3691
_reflns_number_total             4487
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra18985c1.cif
_cod_data_source_block           131205_s1_lh
_cod_original_cell_volume        1391.86(9)
_cod_database_code               7223092
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h12n2o3s1
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.952
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
 H2-H15a
 1.92 with sigma of 0.002
 O7-H7d
 0.89 with sigma of 0.002
3.a Ternary CH refined with riding coordinates:
 C6(H6), C17(H17), C10(H10), C9(H9), C14(H14), C4(H4), C21(H21), C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C25(H25a,H25b), C26(H26a,H26b), C7(H7a,H7b), C23(H23a,H23b),
 C16(H16a,H16b), C12(H12a,H12b), C15(H15a,H15b), C5(H5a,H5b), C22(H22a,H22b),
 C11(H11a,H11b), C3(H3a,H3b)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1a)
3.d Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c), C20(H20a,H20b,H20c), C18(H18a,H18b,H18c)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              93877
_olex2_submission_special_instructions 'No special instructions were received'