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_7248535
_publ_section_title
;
 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      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_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                 114.231(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.106(4)
_cell_length_b                   5.4996(10)
_cell_length_c                   23.399(5)
_cell_measurement_reflns_used    1220
_cell_measurement_temperature    170
_cell_measurement_theta_max      23.116
_cell_measurement_theta_min      2.259
_cell_volume                     2359.4(8)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.953
_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_unetI/netI     0.0899
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4448
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.672
_diffrn_reflns_theta_min         1.909
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7523
_exptl_absorpt_correction_T_min  0.5236
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 20923 reflections, Rint = 0.0911
 (6016 with I > 3sig(I), Rint = 0.0543)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         4448
_refine_ls_number_restraints     759
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1541
_refine_ls_R_factor_gt           0.0993
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0173P)^2^+9.7206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1837
_refine_ls_wR_factor_ref         0.2087
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2853
_reflns_number_total             4448
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00259h2.cif
_cod_data_source_block           mo_20231102_0m_4
_cod_depositor_comments
'Adding full bibliography for 7248532--7248536.cif.'
_cod_database_code               7248535
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.988
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6350(16)
 0.3650(16)
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. Restrained distances
 C22-C26 \\sim C27-C26
 with sigma of 0.02
4. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C23) \\sim Ueq, Uanis(C22) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C27) \\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
6. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Fixed Sof: N2(0.6) H2C(0.6) H2D(0.6) C30(0.6) H30A(0.6) H30B(0.6) C29(0.6)
 H29A(0.6) H29B(0.6) C27(0.6) H27(0.6) C28(0.6) H28A(0.6) H28B(0.6) C23(0.4)
 H23A(0.4) H23B(0.4) C24(0.4) H24A(0.4) H24B(0.4) C25(0.4) H25A(0.4) H25B(0.4)
 N1(0.4) H1C(0.4) H1D(0.4) C22(0.4) H22(0.4)
8.a Ternary CH refined with riding coordinates:
 C27(H27), C22(H22)
8.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C2(H2A,H2B), C1(H1A,H1B), N2(H2C,H2D), C30(H30A,
 H30B), C29(H29A,H29B), C28(H28A,H28B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B), N1(H1C,H1D)
8.c Aromatic/amide H refined with riding coordinates:
 C4(H4A), C19(H19), C9(H9), C16(H16), C12(H12), C20(H20), C13(H13)
8.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C14(H14A,H14B,H14C)
8.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O2(H2), O4(H4)
;
_shelx_res_checksum              99160
_olex2_submission_special_instructions 'No special instructions were received'