Probing the Relationship between Gelation and Crystallization by Using Salts of Lithocholic Acid
Li, Puzhen; Zhang, Meng; Maris, Thierry; Zhu, X. X.; Wuest, James D.; Crystal Growth & Design 22 (2021) 643–652; doi:10.1021/acs.cgd.1c01182

data_4519269
_publ_section_title
;
 Probing the Relationship between Gelation and Crystallization by Using
 Salts of Lithocholic Acid
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              643
_journal_page_last               652
_journal_paper_doi               10.1021/acs.cgd.1c01182
_journal_volume                  22
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H39 O3, C6 H14 N'
_chemical_formula_sum            'C30 H53 N O3'
_chemical_formula_weight         475.73
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_contact_author_name
;
;
_audit_creation_date             2021-05-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.761(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1747(4)
_cell_length_b                   7.5361(3)
_cell_length_c                   17.8459(7)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.621
_cell_measurement_theta_min      2.586
_cell_volume                     1439.02(10)
_computing_cell_refinement
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25275
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.960
_diffrn_reflns_theta_min         2.586
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.65
_diffrn_source_power             0.0291265
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           44.81
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.5817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1534 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.7720.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_description       Block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 2220 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         5412
_refine_ls_number_restraints     401
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0835P)^2^+0.2872P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1250
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                5260
_reflns_number_total             5412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            LCA-CycloHexylNH3_zhu22.cif
_cod_data_source_block           zhu22
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the built-in table derived from the CIF
Core dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_database_code               4519269
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.840
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Shared sites
{N1A, N1B}
3. Uiso/Uaniso restraints and constraints
N1A \\sim C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A \\sim N1B \\sim
C1B \\sim C2B \\sim C3B \\sim C4B \\sim C5B \\sim C6B \\sim N1C \\sim C1C \\sim
C2C \\sim C3C \\sim C4C \\sim C5C \\sim C6C: within 1.7A with sigma of 0.005
and sigma for terminal atoms of 0.02 within 1.7A
Uanis(N1A) = Uanis(N1B) = Uanis(N1C)
4. Same fragment restrains
{N1B, C1B, C2B, C3B, C4B, C5B, C6B} sigma for 1-2: 0.001, 1-3: 0.01
as in
{N1C, C1C, C2C, C3C, C4C, C5C, C6C}
5. Others
 1*[Sof(N1A)+Sof(H1AA)+Sof(H1AB)+Sof(H1AC)+Sof(C1A)+Sof(H1AD)+Sof(C2A)+
 Sof(H2AA)+Sof(H2AB)+Sof(C3A)+Sof(H3AA)+Sof(H3AB)+Sof(C4A)+Sof(H4AA)+Sof(H4AB)+
 Sof(C5A)+Sof(H5AA)+Sof(H5AB)+Sof(C6A)+Sof(H6AA)+Sof(H6AB)]+1*[Sof(N1B)+
 Sof(H1BA)+Sof(H1BB)+Sof(H1BC)+Sof(C1B)+Sof(H1BD)+Sof(C2B)+Sof(H2BA)+Sof(H2BB)+
 Sof(C3B)+Sof(H3BA)+Sof(H3BB)+Sof(C4B)+Sof(H4BA)+Sof(H4BB)+Sof(C5B)+Sof(H5BA)+
 Sof(H5BB)+Sof(C6B)+Sof(H6BA)+Sof(H6BB)]+1*[Sof(N1C)+Sof(H1CA)+Sof(H1CB)+
 Sof(H1CC)+Sof(C1C)+Sof(H1C)+Sof(C2C)+Sof(H2CA)+Sof(H2CB)+Sof(C3C)+Sof(H3CA)+
 Sof(H3CB)+Sof(C4C)+Sof(H4CA)+Sof(H4CB)+Sof(C5C)+Sof(H5CA)+Sof(H5CB)+Sof(C6C)+
 Sof(H6CA)+Sof(H6CB)]=1 with esd of 0.001
 Sof(N1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C1A)=Sof(H1AD)=Sof(C2A)=Sof(H2AA)=
 Sof(H2AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=
 Sof(H5AA)=Sof(H5AB)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=FVAR(1)
 Sof(N1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C1B)=Sof(H1BD)=Sof(C2B)=Sof(H2BA)=
 Sof(H2BB)=Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(C5B)=
 Sof(H5BA)=Sof(H5BB)=Sof(C6B)=Sof(H6BA)=Sof(H6BB)=FVAR(2)
 Sof(N1C)=Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=Sof(C1C)=Sof(H1C)=Sof(C2C)=Sof(H2CA)=
 Sof(H2CB)=Sof(C3C)=Sof(H3CA)=Sof(H3CB)=Sof(C4C)=Sof(H4CA)=Sof(H4CB)=Sof(C5C)=
 Sof(H5CA)=Sof(H5CB)=Sof(C6C)=Sof(H6CA)=Sof(H6CB)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C9(H9), C14(H14), C17(H17), C20(H20), C1A(H1AD),
 C1B(H1BD), C1C(H1C)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,
 H11B), C12(H12A,H12B), C15(H15A,H15B), C16(H16A,H16B), C22(H22A,H22B),
 C23(H23A,H23B), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB),
  C6A(H6AA,H6AB), C2B(H2BA,H2BB), C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5B(H5BA,
 H5BB), C6B(H6BA,H6BB), C2C(H2CA,H2CB), C3C(H3CA,H3CB), C4C(H4CA,H4CB),
 C5C(H5CA,H5CB), C6C(H6CA,H6CB)
6.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), N1A(H1AA,H1AB,
 H1AC), N1B(H1BA,H1BB,H1BC), N1C(H1CA,H1CB,H1CC)
6.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_cod_database_fobs_code 4519269