#------------------------------------------------------------------------------
#$Date: 2021-03-05 04:26:42 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262726 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157854.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7157854
loop_
_publ_author_name
'Xie, Wucheng'
'Jian, Xinyi'
'Zhang, Liyang'
'Jin, Kexin'
'Shi, Junjun'
'Zhu, Feng'
_publ_section_title
;
 Synthesis of C3-sulfone substituted naphthols via
 rhodium(III)-catalyzed annulation of sulfoxonium ylides with
 alkynylsulfones.
;
_journal_issue                   7
_journal_name_full               'Organic & 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         'C24 H20 O3 S'
_chemical_formula_sum            'C24 H20 O3 S'
_chemical_formula_weight         388.46
_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
_audit_creation_date             2019-09-08
_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                116.288(8)
_cell_angle_beta                 102.125(7)
_cell_angle_gamma                97.876(6)
_cell_formula_units_Z            2
_cell_length_a                   8.1695(6)
_cell_length_b                   11.1838(9)
_cell_length_c                   12.1869(10)
_cell_measurement_reflns_used    2997
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      28.4920
_cell_measurement_theta_min      2.6390
_cell_volume                     941.83(16)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  37.00   1.00    1.50    --   11.74 -57.00   0.00   93
  2  ω    -16.00  10.00   1.00    1.50    --   11.74 -99.00   0.00   26
  3  ω    -13.00  84.00   1.00    1.50    --   11.74  57.00 150.00   97
  4  ω    -13.00  78.00   1.00    1.50    --   11.74  77.00 -90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0212453000
_diffrn_orient_matrix_UB_12      -0.0291997000
_diffrn_orient_matrix_UB_13      0.0379799000
_diffrn_orient_matrix_UB_21      -0.0779884000
_diffrn_orient_matrix_UB_22      0.0212445000
_diffrn_orient_matrix_UB_23      -0.0029774000
_diffrn_orient_matrix_UB_31      -0.0440003000
_diffrn_orient_matrix_UB_32      -0.0637972000
_diffrn_orient_matrix_UB_33      -0.0565192000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6644
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.957
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64178
_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    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.058
_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     256
_refine_ls_number_reflns         3321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0441
_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/[σ²(Fo²)+(0.0555P)²+0.2895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1163
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2770
_reflns_number_total             3321
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob02267e2.cif
_cod_data_source_block           fs02
_cod_depositor_comments
'Adding full bibliography for 7157853--7157854.cif.'
_cod_original_cell_volume        941.83(14)
_cod_database_code               7157854
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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:
 C8(H8), C5(H5), C16(H16), C18(H18), C2(H2), C22(H22), C12(H12), C14(H14),
 C19(H19), C13(H13), C3(H3), C21(H21), C15(H15)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.649
_oxdiff_exptl_absorpt_empirical_full_min 0.697
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.98203(7) 0.28958(5) 0.72564(5) 0.01752(17) Uani 1 1 d . . . . .
O1 O 0.61586(18) -0.10402(13) 0.28169(13) 0.0206(4) Uani 1 1 d . . . . .
H1 H 0.704013 -0.129977 0.292796 0.031 Uiso 1 1 calc GR . . . .
O2 O 0.94677(18) 0.30089(14) 0.83996(13) 0.0209(4) Uani 1 1 d . . . . .
O3 O 1.10241(18) 0.20975(14) 0.67990(14) 0.0231(4) Uani 1 1 d . . . . .
C8 C 0.7793(3) 0.0873(2) 0.4897(2) 0.0176(5) Uani 1 1 d . . . . .
H8 H 0.875280 0.051204 0.490016 0.021 Uiso 1 1 calc R . . . .
C7 C 0.6317(3) 0.0177(2) 0.38693(19) 0.0166(5) Uani 1 1 d . . . . .
C5 C 0.3303(3) 0.0031(2) 0.2797(2) 0.0177(5) Uani 1 1 d . . . . .
H5 H 0.325879 -0.079810 0.209782 0.021 Uiso 1 1 calc R . . . .
C9 C 0.7861(3) 0.2135(2) 0.59496(19) 0.0155(4) Uani 1 1 d . . . . .
C4 C 0.1878(3) 0.0553(2) 0.2782(2) 0.0180(5) Uani 1 1 d . . . . .
C6 C 0.4840(3) 0.0727(2) 0.38532(19) 0.0159(4) Uani 1 1 d . . . . .
C1 C 0.4938(3) 0.2006(2) 0.49257(19) 0.0162(4) Uani 1 1 d . . . . .
C11 C 0.6565(3) 0.4113(2) 0.7075(2) 0.0174(5) Uani 1 1 d . . . . .
C10 C 0.6485(3) 0.2741(2) 0.6000(2) 0.0168(5) Uani 1 1 d . . . . .
C17 C 1.0663(3) 0.4577(2) 0.7528(2) 0.0176(5) Uani 1 1 d . . . . .
C16 C 0.6744(3) 0.5273(2) 0.6907(2) 0.0214(5) Uani 1 1 d . . . . .
H16 H 0.683303 0.518585 0.612817 0.026 Uiso 1 1 calc R . . . .
C18 C 1.1081(3) 0.5677(2) 0.8753(2) 0.0213(5) Uani 1 1 d . . . . .
H18 H 1.080249 0.555266 0.940412 0.026 Uiso 1 1 calc R . . . .
C2 C 0.3428(3) 0.2505(2) 0.4898(2) 0.0203(5) Uani 1 1 d . . . . .
H2 H 0.343618 0.332483 0.559168 0.024 Uiso 1 1 calc R . . . .
C22 C 1.1024(3) 0.4762(2) 0.6535(2) 0.0222(5) Uani 1 1 d . . . . .
H22 H 1.070968 0.401788 0.570794 0.027 Uiso 1 1 calc R . . . .
C20 C 1.2338(3) 0.7184(2) 0.8033(2) 0.0218(5) Uani 1 1 d . . . . .
C12 C 0.6397(3) 0.4268(2) 0.8248(2) 0.0199(5) Uani 1 1 d . . . . .
H12 H 0.624201 0.350499 0.837566 0.024 Uiso 1 1 calc R . . . .
C14 C 0.6655(3) 0.6694(2) 0.9040(2) 0.0249(5) Uani 1 1 d . . . . .
H14 H 0.669313 0.755387 0.969532 0.030 Uiso 1 1 calc R . . . .
C19 C 1.1924(3) 0.6969(2) 0.8994(2) 0.0232(5) Uani 1 1 d . . . . .
H19 H 1.222135 0.771393 0.981951 0.028 Uiso 1 1 calc R . . . .
C13 C 0.6460(3) 0.5553(2) 0.9218(2) 0.0220(5) Uani 1 1 d . . . . .
H13 H 0.637027 0.564943 0.999988 0.026 Uiso 1 1 calc R . . . .
C3 C 0.1962(3) 0.1794(2) 0.3864(2) 0.0214(5) Uani 1 1 d . . . . .
H3 H 0.099102 0.214127 0.387494 0.026 Uiso 1 1 calc R . . . .
C21 C 1.1850(3) 0.6062(2) 0.6797(2) 0.0243(5) Uani 1 1 d . . . . .
H21 H 1.208647 0.619129 0.613694 0.029 Uiso 1 1 calc R . . . .
C15 C 0.6792(3) 0.6545(2) 0.7874(2) 0.0254(5) Uani 1 1 d . . . . .
H15 H 0.691698 0.730817 0.774497 0.030 Uiso 1 1 calc R . . . .
C23 C 1.3337(3) 0.8584(2) 0.8334(2) 0.0305(6) Uani 1 1 d . . . . .
H23A H 1.331973 0.926864 0.915739 0.046 Uiso 1 1 calc GR . . . .
H23B H 1.281295 0.880084 0.768621 0.046 Uiso 1 1 calc GR . . . .
H23C H 1.451498 0.857478 0.835057 0.046 Uiso 1 1 calc GR . . . .
C24 C 0.0255(3) -0.0141(2) 0.1652(2) 0.0246(5) Uani 1 1 d . . . . .
H24A H 0.005816 0.046522 0.130311 0.037 Uiso 1 1 calc GR . . . .
H24B H -0.071402 -0.034937 0.192512 0.037 Uiso 1 1 calc GR . . . .
H24C H 0.038533 -0.098075 0.100523 0.037 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 117.57(9) . . ?
O2 S1 C9 110.22(9) . . ?
O2 S1 C17 108.33(9) . . ?
O3 S1 C9 105.85(9) . . ?
O3 S1 C17 106.97(9) . . ?
C17 S1 C9 107.44(10) . . ?
C7 O1 H1 109.5 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.15(18) . . ?
C9 C8 H8 119.9 . . ?
O1 C7 C8 123.49(17) . . ?
O1 C7 C6 116.23(18) . . ?
C8 C7 C6 120.28(18) . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.45(18) . . ?
C6 C5 H5 119.3 . . ?
C8 C9 S1 115.65(15) . . ?
C10 C9 S1 121.38(15) . . ?
C10 C9 C8 122.9(2) . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 C24 122.41(18) . . ?
C3 C4 C24 119.33(18) . . ?
C5 C6 C7 121.30(18) . . ?
C5 C6 C1 120.03(18) . . ?
C1 C6 C7 118.67(19) . . ?
C6 C1 C10 121.20(18) . . ?
C2 C1 C6 117.3(2) . . ?
C2 C1 C10 121.51(18) . . ?
C16 C11 C10 119.92(18) . . ?
C16 C11 C12 118.17(18) . . ?
C12 C11 C10 121.86(18) . . ?
C9 C10 C1 116.77(17) . . ?
C9 C10 C11 123.68(19) . . ?
C1 C10 C11 119.51(17) . . ?
C18 C17 S1 118.83(16) . . ?
C18 C17 C22 121.09(19) . . ?
C22 C17 S1 119.88(16) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 C11 121.2(2) . . ?
C15 C16 H16 119.4 . . ?
C17 C18 H18 120.7 . . ?
C17 C18 C19 118.6(2) . . ?
C19 C18 H18 120.7 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.85(19) . . ?
C3 C2 H2 119.6 . . ?
C17 C22 H22 120.4 . . ?
C21 C22 C17 119.2(2) . . ?
C21 C22 H22 120.4 . . ?
C19 C20 C21 118.3(2) . . ?
C19 C20 C23 120.7(2) . . ?
C21 C20 C23 121.0(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.25(19) . . ?
C13 C12 H12 119.9 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.37(19) . . ?
C15 C14 H14 120.3 . . ?
C18 C19 C20 121.8(2) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C4 C3 H3 119.0 . . ?
C2 C3 C4 122.09(19) . . ?
C2 C3 H3 119.0 . . ?
C22 C21 C20 121.0(2) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C4 C24 H24A 109.5 . . ?
C4 C24 H24B 109.5 . . ?
C4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4361(14) . ?
S1 O3 1.4509(14) . ?
S1 C9 1.783(2) . ?
S1 C17 1.766(2) . ?
O1 H1 0.8200 . ?
O1 C7 1.360(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.368(3) . ?
C8 C9 1.410(3) . ?
C7 C6 1.428(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.372(3) . ?
C5 C6 1.416(3) . ?
C9 C10 1.388(3) . ?
C4 C3 1.409(3) . ?
C4 C24 1.504(3) . ?
C6 C1 1.424(3) . ?
C1 C10 1.433(3) . ?
C1 C2 1.422(3) . ?
C11 C10 1.493(3) . ?
C11 C16 1.394(3) . ?
C11 C12 1.401(3) . ?
C17 C18 1.379(3) . ?
C17 C22 1.395(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.377(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.379(3) . ?
C20 C19 1.391(3) . ?
C20 C21 1.393(3) . ?
C20 C23 1.506(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.380(3) . ?
C14 C15 1.386(3) . ?
C19 H19 0.9300 . ?
C13 H13 0.9300 . ?
C3 H3 0.9300 . ?
C21 H21 0.9300 . ?
C15 H15 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
