New solid forms of tetrahydrocurcumin with improved solubility
Tian, Fanyu; Xia, Mengyuan; Wang, Hao; Zhang, Bingrui; Ding, Zhenfeng; Rong, Xiaoyi; Zhu, Bingqing; Mei, Xuefeng; CrystEngComm 26 (2024) 3232–3239; doi:10.1039/D4CE00259H

data_7248534
_publ_section_title
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 New solid forms of tetrahydrocurcumin with improved solubility
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              3232
_journal_page_last               3239
_journal_paper_doi               10.1039/D4CE00259H
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C21 H24 O6, C5 H9 N O2'
_chemical_formula_sum            'C26 H33 N O8'
_chemical_formula_weight         487.53
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-02-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-02-21 deposited with the CCDC.	2024-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.370(4)
_cell_length_b                   23.190(8)
_cell_length_c                   5.4660(16)
_cell_measurement_reflns_used    2899
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.412
_cell_measurement_theta_min      2.218
_cell_volume                     2328.5(12)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            17672
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.411
_diffrn_reflns_theta_min         2.077
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1196 before and 0.0637 after correction. The Ratio of minimum to maximum transmission is 0.8646. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0657
_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^)+(0.0608P)^2^+1.5797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1592
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3277
_reflns_number_total             4722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00259h2.cif
_cod_data_source_block           mo_2023137_0m
_cod_depositor_comments
'Adding full bibliography for 7248532--7248536.cif.'
_cod_database_code               7248534
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0(2)
 1(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C22(H22)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C2(H2a,H2b), C6(H6a,H6b), C7(H7a,H7b), N1(H1c,H1d), C24(H24a,
 H24b), C25(H25a,H25b), C23(H23a,H23b)
3.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C12(H12), C4(H4a), C13(H13), C19(H19), C20(H20), C9(H9)
3.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C21(H21a,H21b,H21c)
3.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6), O2(H2)
;
_shelx_res_checksum              47874
_olex2_submission_special_instructions 'No special instructions were received'