Synthesis of C3-sulfone substituted naphthols <i>via</i> rhodium(III)-catalyzed annulation of sulfoxonium ylides with alkynylsulfones.
Xie, Wucheng; Jian, Xinyi; Zhang, Liyang; Jin, Kexin; Shi, Junjun; Zhu, Feng; Organic & biomolecular chemistry 19 (2021) 1498–1502; doi:10.1039/d0ob02267e

data_7157853
_publ_section_title
;
 Synthesis of C3-sulfone substituted naphthols <i>via</i>
 rhodium(III)-catalyzed annulation of sulfoxonium ylides with
 alkynylsulfones.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1498
_journal_page_last               1502
_journal_paper_doi               10.1039/d0ob02267e
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C23 H18 O3 S'
_chemical_formula_sum            'C23 H18 O3 S'
_chemical_formula_weight         374.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-08-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-13 deposited with the CCDC.	2021-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                115.047(11)
_cell_angle_beta                 104.819(8)
_cell_angle_gamma                94.550(7)
_cell_formula_units_Z            2
_cell_length_a                   8.4310(5)
_cell_length_b                   10.6418(11)
_cell_length_c                   11.6712(14)
_cell_measurement_reflns_used    2856
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.7830
_cell_measurement_theta_min      3.4990
_cell_volume                     895.84(19)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -34.00  54.00   1.00    2.50    --  -11.43  57.00 -90.00   88
  2  \w    -85.00  16.00   1.00    2.50    --  -11.43 -57.00 120.00  101
  3  \w    -14.00  76.00   1.00    2.50    --   11.74  77.00  30.00   90
;
_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      -0.0166877000
_diffrn_orient_matrix_UB_12      -0.0461520000
_diffrn_orient_matrix_UB_13      0.0270022000
_diffrn_orient_matrix_UB_21      0.0240094000
_diffrn_orient_matrix_UB_22      0.0588589000
_diffrn_orient_matrix_UB_23      0.0645404000
_diffrn_orient_matrix_UB_31      -0.0841584000
_diffrn_orient_matrix_UB_32      0.0088631000
_diffrn_orient_matrix_UB_33      -0.0109607000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5678
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.033
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92363
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.603
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0743
_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^)+27.8932P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2661
_reflns_number_total             3149
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02267e2.cif
_cod_data_source_block           fs0827
_cod_depositor_comments
'Adding full bibliography for 7157853--7157854.cif.'
_cod_original_cell_volume        895.84(17)
_cod_database_code               7157853
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.976
_reflns_odcompleteness_completeness 99.97
_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.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C16(H16), C9(H9), C18(H18), C2(H2), C7(H7), C12(H12), C22(H22),
 C8(H8), C13(H13), C15(H15), C14(H14), C21(H21), C19(H19)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 1.209
_oxdiff_exptl_absorpt_empirical_full_min 0.778