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_4519348
_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_absolute_configuration ad
_chemical_formula_moiety         'C19 H14 Cl2 O2'
_chemical_formula_sum            'C19 H14 Cl2 O2'
_chemical_formula_weight         345.20
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-12
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.0800(11)
_cell_length_b                   27.367(8)
_cell_length_c                   5.5795(14)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      31.5538
_cell_measurement_theta_min      2.9773
_cell_volume                     775.7(3)
_computing_cell_refinement       'SAINT+ Ver. 2018.1-0. (Bruker-AXS, 2018)'
_computing_data_collection       'APEX3 Ver. 2018.1-0. (Bruker-AXS, 2018)'
_computing_data_reduction        'SAINT+ Ver. 2018.1-0. (Bruker-AXS, 2018)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            18806
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.572
_diffrn_reflns_theta_min         1.488
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.7071
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1010 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         2597
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0226
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0282P)^2^+0.1760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0610
_reflns_Friedel_coverage         0.663
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2557
_reflns_number_total             2597
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c07006_si_005.cif
_cod_data_source_block           stepanova01
_cod_database_code               4519348
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.883
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O1-H1
 0.84 with sigma of 0.01
3. Others
 Fixed Sof: H1(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10)
;
_shelx_res_checksum              94968
_shelx_hkl_checksum              522
_olex2_submission_special_instructions 'No special instructions were received'