Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free Approach to Curcuminoids
Stepanova, Valeria A.; Guerrero, Andres; Schull, Cullen; Christensen, Joshua; Trudeau, Claire; Cook, Joshua; Wolmutt, Kyle; Blochwitz, Jordan; Ismail, Abdelrahman; West, Joseph K.; Wheaton, Amelia M.; Guzei, Ilia A.; Yao, Bin; Kubatova, Alena; ACS Omega 7 (2022) 7257–7277; doi:10.1021/acsomega.1c07006

data_4519345
_publ_section_title
;
 Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free
 Approach to Curcuminoids
;
_journal_issue                   8
_journal_name_full               'ACS Omega'
_journal_page_first              7257
_journal_page_last               7277
_journal_paper_doi               10.1021/acsomega.1c07006
_journal_volume                  7
_journal_year                    2022
_chemical_formula_moiety         'C24 H33 B3 N2 O8, C0.938 H1.877 Cl1.877'
_chemical_formula_sum            'C24.94 H34.88 B3 Cl1.88 N2 O8'
_chemical_formula_weight         589.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-25
_audit_creation_method
;
Olex2 1.3-beta
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.232(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.071(3)
_cell_length_b                   7.8493(16)
_cell_length_c                   21.159(3)
_cell_measurement_reflns_used    8726
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      70.088
_cell_measurement_theta_min      2.947
_cell_volume                     2943.8(9)
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_collection
'Bruker Instrument Service, BIS, v.6.2.12 (Bruker AXS Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       '\k-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '0.5\% \w and 0.5\% \f scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON III'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26354
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.139
_diffrn_reflns_theta_min         2.946
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.294
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       plate
_exptl_crystal_F_000             1238
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         5508
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0411P)^2^+0.5803P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4232
_reflns_number_total             5508
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c07006_si_002.cif
_cod_data_source_block           stepanova09
_cod_database_code               4519345
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.934
_olex2_refinement_description
;
1. 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
2. Restrained distances
 O1-H1
 0.87 with sigma of 0.01
 Cl2A-C25A = Cl1-C25A
 1.7602 with sigma of 0.01
 Cl1-Cl2A
 2.9338 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uiso(C25A) = Uiso(Cl2A)
Uiso(Cl2A) = Uiso(C25A)
4. Others
 -1*[Sof(Cl1)]+1*[Sof(Cl2)+Sof(C25)+Sof(H25A)+Sof(H25B)]+1*[Sof(C25A)+
 Sof(H25C)+Sof(H25D)+Sof(Cl2A)]=0 with esd of 0
 Sof(Cl2)=Sof(C25)=Sof(H25A)=Sof(H25B)=FVAR(2)
 Sof(C25A)=Sof(H25C)=Sof(H25D)=Sof(Cl2A)=FVAR(3)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C21(H21A,H21B), C22(H22A,H22B),
 C23(H23A,H23B), C25(H25A,H25B), C25A(H25C,H25D)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C15(H15), C16(H16), C17(H17), C19(H19)
5.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C20(H20A,H20B,H20C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              44308
_shelx_hkl_checksum              74119
_olex2_submission_special_instructions 'No special instructions were received'