Sulfoxide-mediated oxidative cross-coupling of phenols
He, Zhen; Perry, Gregory J. P.; Procter, David J.; Chemical Science 11 (2020) 2001–2005; doi:10.1039/C9SC05668H

data_1557086
_publ_section_title
;
 Sulfoxide-mediated oxidative cross-coupling of phenols
;
_journal_issue                   7
_journal_name_full               'Chemical Science'
_journal_page_first              2001
_journal_page_last               2005
_journal_paper_doi               10.1039/C9SC05668H
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C25 H28 O8'
_chemical_formula_sum            'C25 H28 O8'
_chemical_formula_weight         456.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-01 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.730(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.9022(18)
_cell_length_b                   11.0935(6)
_cell_length_c                   13.4816(7)
_cell_measurement_reflns_used    4608
_cell_measurement_temperature    149.9(3)
_cell_measurement_theta_max      28.4220
_cell_measurement_theta_min      2.9930
_cell_volume                     4407.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      149.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.860
_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    -88.00   3.00   1.00    9.49    --  -18.77 -57.00 -90.00   91
  2  \w    -20.00  25.00   1.00    9.49    --  -18.77 -99.00-180.00   45
  3  \w    -39.00  19.00   1.00    9.49    --  -18.77  57.00  60.00   58
  4  \w     -7.00  90.00   1.00    9.49    --   20.02  38.00-150.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0205143000
_diffrn_orient_matrix_UB_12      -0.0333884000
_diffrn_orient_matrix_UB_13      -0.0086318000
_diffrn_orient_matrix_UB_21      -0.0125531000
_diffrn_orient_matrix_UB_22      0.0541374000
_diffrn_orient_matrix_UB_23      0.0012469000
_diffrn_orient_matrix_UB_31      -0.0010397000
_diffrn_orient_matrix_UB_32      0.0068427000
_diffrn_orient_matrix_UB_33      -0.0526147000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12291
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.150
_diffrn_reflns_theta_min         2.764
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       prism
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0434P)^2^+5.6515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1334
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3801
_reflns_number_total             5108
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05668h2.cif
_cod_data_source_block           adjp393
_cod_depositor_comments
;Adding full bibliography for 1557082--1557086.cif.

 Adding full bibliography for 1557082--1557086.cif.
;
_cod_database_code               1557086
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: C1(0.5) C2(0.5) H2A(0.5) H1A(0.5) H2B(0.5) H1B(0.5) H1C(0.5)
 H2C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O)
3.b Idealised Me refined as rotating group:
 C00R(H00A,H00D,H00E), C00S(H00F,H00G,H00H), C00T(H00I,H00J,H00N), C00U(H00P,
 H00Q,H00R), C00V(H00S,H00T,H00U), C00W(H00V,H00W,H00X)
3.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_olex2_date_sample_data_collection 2019-06-06
_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 1.994
_oxdiff_exptl_absorpt_empirical_full_min 0.359