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_7124239
_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_formula_moiety         'C36 H24 Br Cl O2 S6'
_chemical_formula_sum            'C36 H24 Br Cl O2 S6'
_chemical_formula_weight         796.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-26
_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                 91.184(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.920(3)
_cell_length_b                   6.6165(9)
_cell_length_c                   29.427(4)
_cell_measurement_reflns_used    2063
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      26.2810
_cell_measurement_theta_min      2.5810
_cell_volume                     3683.0(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     14.00  82.00   1.00    9.00    --   11.74  57.00  90.00   68
  2  \w    -15.00  78.00   1.00    9.00    --   11.74  57.00-150.00   93
  3  \w    -55.00 -29.00   1.00    9.00    --   11.74 -57.00 120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0374969000
_diffrn_orient_matrix_UB_12      0.0001806000
_diffrn_orient_matrix_UB_13      -0.0000768000
_diffrn_orient_matrix_UB_21      -0.0008880000
_diffrn_orient_matrix_UB_22      -0.0018188000
_diffrn_orient_matrix_UB_23      -0.0240973000
_diffrn_orient_matrix_UB_31      -0.0001717000
_diffrn_orient_matrix_UB_32      0.1071965000
_diffrn_orient_matrix_UB_33      -0.0004088000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_av_unetI/netI     0.1180
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            14585
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.153
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.515
_refine_diff_density_min         -1.495
_refine_diff_density_rms         0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6482
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0851
_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^)+(0.1156P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2035
_refine_ls_wR_factor_ref         0.2325
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4232
_reflns_number_total             6482
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06505a2.cif
_cod_data_source_block           mxt-3
_cod_original_cell_volume        3682.9(9)
_cod_database_code               7124239
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.860
_shelx_estimated_absorpt_t_min   0.835
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Rigid bond restraints
 C9, C10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 S1, C7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C9 \\sim C10: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
S1 \\sim C7: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(C32) \\sim Ueq, Uanis(C33) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
4.b Aromatic/amide H refined with riding coordinates:
 C36(H36), C35(H35), C32(H32), C18(H18), C3(H3), C17(H17), C33(H33), C29(H29),
 C2(H2), C30(H30), C25(H25), C5(H5), C21(H21), C22(H22), C6(H6), C24(H24),
 C34(H34), C9(H9), C10(H10)
4.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.481
_oxdiff_exptl_absorpt_empirical_full_min 0.611