Synthesis of Polysubstituted Cyclic 1,2-Diketones Enabled by Iterative Sulfoxide-Mediated Arylation
Meng, Xiangtai; Chen, Dengfeng; Cao, Xiaoji; Luo, Jinyue; Wang, Fei; Huang, Shenlin; Chemical Communications  (2019) –; doi:10.1039/C9CC06505A

data_7124238
_publ_section_title
;
 Synthesis of Polysubstituted Cyclic 1,2-Diketones Enabled by Iterative
 Sulfoxide-Mediated Arylation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06505A
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H32 O3 S2'
_chemical_formula_sum            'C29 H32 O3 S2'
_chemical_formula_weight         492.66
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-04 deposited with the CCDC.    2019-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2472(8)
_cell_length_b                   13.6858(14)
_cell_length_c                   19.2652(15)
_cell_measurement_reflns_used    4198
_cell_measurement_temperature    283(2)
_cell_measurement_theta_max      25.20
_cell_measurement_theta_min      2.44
_cell_volume                     2438.1(4)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      283.47
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.1016
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12728
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.443
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1009 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1475
_refine_ls_R_factor_gt           0.0638
_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^)+(0.0496P)^2^+1.2528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1418
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                3299
_reflns_number_total             5440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06505a2.cif
_cod_data_source_block           8
_cod_database_code               7124238
_shelx_shelxl_version_number     2018/3
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C4(H4A,H4B), C5(H5A,H5B), C11(H11A,H11B),
 C16(H16A,H16B), C12(H12A,H12B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C29(H29), C22(H22), C25(H25), C28(H28), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              86730
_olex2_submission_special_instructions 'No special instructions were received'