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_7248533
_publ_section_title
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 New solid forms of tetrahydrocurcumin with improved solubility
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_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         '0.5(C42 H48 O12), C10 H8 N2'
_chemical_formula_sum            'C31 H32 N2 O6'
_chemical_formula_weight         528.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 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                 101.980(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.421(5)
_cell_length_b                   6.843(3)
_cell_length_c                   14.762(4)
_cell_measurement_reflns_used    1179
_cell_measurement_temperature    170
_cell_measurement_theta_max      23.31
_cell_measurement_theta_min      2.82
_cell_volume                     1326.2(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 0.997
_diffrn_measured_fraction_theta_max 0.991
_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  0.0545
_diffrn_reflns_av_unetI/netI     0.0823
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5043
_diffrn_reflns_point_group_measured_fraction_full 0.897
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_min         2.821
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0719 before and 0.0610 after correction.
The Ratio of minimum to maximum transmission is 0.8685.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         2378
_refine_ls_number_restraints     705
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0719
_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^)+(0.0815P)^2^+2.1188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1985
_reflns_Friedel_coverage         0.619
_reflns_Friedel_fraction_full    0.777
_reflns_Friedel_fraction_max     0.732
_reflns_number_gt                1550
_reflns_number_total             2378
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00259h2.cif
_cod_data_source_block           mo_2022905_0m
_cod_depositor_comments
'Adding full bibliography for 7248532--7248536.cif.'
_cod_database_code               7248533
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.993
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 2(4)
 -1(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. 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
4. 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(C7) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(O2) \\sim
Ueq, Uanis(C21) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(O6)
\\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq,
Uanis(C20) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2)
\\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq,
Uanis(C10) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq,
Uanis(C26) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23)
\\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(O2) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
5. 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
6. Others
 Fixed Sof: O1(0.5) H1(0.5) O2(0.5) O4(0.5) H4(0.5) O6(0.5) H6(0.5) O3(0.5)
 O5(0.5) C11(0.5) C3(0.5) C5(0.5) C13(0.5) H13(0.5) C20(0.5) H20(0.5) C19(0.5)
 H19(0.5) C18(0.5) C17(0.5) C16(0.5) H16(0.5) C15(0.5) C12(0.5) H12(0.5)
 C10(0.5) C9(0.5) H9(0.5) C2(0.5) H2a(0.5) H2b(0.5) C6(0.5) H6a(0.5) H6b(0.5)
 C8(0.5) H4a(0.5) C1(0.5) H1a(0.5) H1b(0.5) C7(0.5) H7a(0.5) H7b(0.5) C14(0.5)
 H14a(0.5) H14b(0.5) H14c(0.5) C21(0.5) H21a(0.5) H21b(0.5) H21c(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C6(H6a,H6b), C1(H1a,H1b), C7(H7a,H7b)
7.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C20(H20), C19(H19), C16(H16), C12(H12), C25(H25), C26(H26),
 C22(H22), C23(H23), C9(H9), C4(H4a)
7.c Fitted hexagon refined as free rotating group:
 C20(C19,C18,C17,C16,C15), C25(C26,N1,C22,C23,C24)
7.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C21(H21a,H21b,H21c)
7.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O6(H6)
;
_shelx_res_checksum              6764
_olex2_submission_special_instructions 'No special instructions were received'