#------------------------------------------------------------------------------
#$Date: 2021-03-05 04:26:42 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262726 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157853.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_7157853
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         '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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  54.00   1.00    2.50    --  -11.43  57.00 -90.00   88
  2  ω    -85.00  16.00   1.00    2.50    --  -11.43 -57.00 120.00  101
  3  ω    -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       'ω 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/[σ²(Fo²)+27.8932P] where P=(Fo²+2Fc²)/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 > 2σ(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_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.
;
_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
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 0.01861(16) 0.70288(12) 0.28163(11) 0.0107(3) Uani 1 1 d . . . . .
O3 O 0.3778(5) 1.1123(4) 0.7276(3) 0.0154(10) Uani 1 1 d . . . . .
H3 H 0.298043 1.147160 0.708404 0.023 Uiso 1 1 calc GR . . . .
O1 O -0.1015(5) 0.7794(4) 0.3351(3) 0.0182(10) Uani 1 1 d . . . . .
O2 O 0.0409(5) 0.7024(4) 0.1634(3) 0.0163(10) Uani 1 1 d . . . . .
C17 C -0.0450(6) 0.5260(5) 0.2495(5) 0.0126(13) Uani 1 1 d . . . . .
C10 C 0.6663(7) 1.0068(5) 0.7245(5) 0.0142(13) Uani 1 1 d . . . . .
H10 H 0.669410 1.092129 0.796028 0.017 Uiso 1 1 calc R . . . .
C16 C 0.3574(7) 0.4627(5) 0.3140(5) 0.0159(14) Uani 1 1 d . . . . .
H16 H 0.355724 0.468913 0.395593 0.019 Uiso 1 1 calc R . . . .
C11 C 0.3532(6) 0.5831(5) 0.2937(5) 0.0126(13) Uani 1 1 d . . . . .
C6 C 0.3542(7) 0.7217(5) 0.4061(5) 0.0140(13) Uani 1 1 d . . . . .
C9 C 0.8096(7) 0.9573(5) 0.7206(5) 0.0146(14) Uani 1 1 d . . . . .
H9 H 0.909829 1.009393 0.789031 0.018 Uiso 1 1 calc R . . . .
C18 C -0.1049(6) 0.4966(5) 0.3375(5) 0.0153(14) Uani 1 1 d . . . . .
H18 H -0.100345 0.569863 0.419114 0.018 Uiso 1 1 calc R . . . .
C2 C 0.2182(6) 0.9105(5) 0.5215(5) 0.0134(13) Uani 1 1 d . . . . .
H2 H 0.120169 0.944411 0.523945 0.016 Uiso 1 1 calc R . . . .
C7 C 0.6604(6) 0.7525(5) 0.5117(5) 0.0144(13) Uani 1 1 d . . . . .
H7 H 0.660300 0.668516 0.440072 0.017 Uiso 1 1 calc R . . . .
C12 C 0.3574(6) 0.5722(5) 0.1710(5) 0.0145(13) Uani 1 1 d . . . . .
H12 H 0.358298 0.651504 0.156252 0.017 Uiso 1 1 calc R . . . .
C1 C 0.2147(6) 0.7807(5) 0.4134(4) 0.0109(12) Uani 1 1 d . . . . .
C3 C 0.3650(6) 0.9860(5) 0.6221(5) 0.0122(13) Uani 1 1 d . . . . .
C22 C -0.0496(7) 0.4171(5) 0.1280(5) 0.0145(13) Uani 1 1 d . . . . .
H22 H -0.009360 0.436473 0.068759 0.017 Uiso 1 1 calc R . . . .
C5 C 0.5075(6) 0.8000(5) 0.5129(5) 0.0119(13) Uani 1 1 d . . . . .
C4 C 0.5143(7) 0.9310(5) 0.6222(5) 0.0120(12) Uani 1 1 d . . . . .
C8 C 0.8076(7) 0.8276(5) 0.6135(5) 0.0178(14) Uani 1 1 d . . . . .
H8 H 0.905571 0.793294 0.612074 0.021 Uiso 1 1 calc R . . . .
C20 C -0.1813(7) 0.2477(5) 0.1799(5) 0.0174(14) Uani 1 1 d . . . . .
C13 C 0.3602(7) 0.4421(6) 0.0713(5) 0.0182(15) Uani 1 1 d . . . . .
H13 H 0.359544 0.434122 -0.011347 0.022 Uiso 1 1 calc R . . . .
C15 C 0.3641(8) 0.3350(6) 0.2149(6) 0.0231(16) Uani 1 1 d . . . . .
H15 H 0.368770 0.256109 0.230134 0.028 Uiso 1 1 calc R . . . .
C14 C 0.3638(7) 0.3251(6) 0.0931(5) 0.0206(16) Uani 1 1 d . . . . .
H14 H 0.366152 0.238737 0.025369 0.025 Uiso 1 1 calc R . . . .
C21 C -0.1153(7) 0.2796(6) 0.0971(5) 0.0181(15) Uani 1 1 d . . . . .
H21 H -0.114732 0.205903 0.017404 0.022 Uiso 1 1 calc R . . . .
C19 C -0.1713(7) 0.3578(5) 0.3031(5) 0.0172(14) Uani 1 1 d . . . . .
H19 H -0.209695 0.337616 0.362670 0.021 Uiso 1 1 calc R . . . .
C23 C -0.2594(8) 0.0984(6) 0.1423(6) 0.0274(17) Uani 1 1 d . . . . .
H23A H -0.375325 0.092011 0.137479 0.041 Uiso 1 1 calc GR . . . .
H23B H -0.201227 0.072348 0.208423 0.041 Uiso 1 1 calc GR . . . .
H23C H -0.251492 0.035281 0.057029 0.041 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
O1 S1 C17 106.5(3) . . ?
O1 S1 C1 105.6(2) . . ?
O2 S1 O1 118.0(3) . . ?
O2 S1 C17 108.8(2) . . ?
O2 S1 C1 108.9(2) . . ?
C17 S1 C1 108.8(2) . . ?
C3 O3 H3 109.5 . . ?
C18 C17 S1 120.7(4) . . ?
C18 C17 C22 120.6(5) . . ?
C22 C17 S1 118.4(5) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C4 120.8(4) . . ?
C4 C10 H10 119.6 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C11 121.0(6) . . ?
C16 C11 C6 119.4(5) . . ?
C12 C11 C16 118.7(5) . . ?
C12 C11 C6 121.8(5) . . ?
C1 C6 C11 124.0(4) . . ?
C1 C6 C5 116.8(4) . . ?
C5 C6 C11 119.2(5) . . ?
C10 C9 H9 119.7 . . ?
C10 C9 C8 120.6(4) . . ?
C8 C9 H9 119.7 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.5(5) . . ?
C19 C18 H18 120.2 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C3 C2 C1 120.1(5) . . ?
C5 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C8 C7 C5 121.6(4) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.5(6) . . ?
C13 C12 H12 120.2 . . ?
C6 C1 S1 122.1(3) . . ?
C6 C1 C2 122.9(4) . . ?
C2 C1 S1 114.9(4) . . ?
O3 C3 C2 123.2(5) . . ?
O3 C3 C4 116.6(4) . . ?
C2 C3 C4 120.2(4) . . ?
C17 C22 H22 120.8 . . ?
C21 C22 C17 118.5(6) . . ?
C21 C22 H22 120.8 . . ?
C7 C5 C6 121.4(4) . . ?
C4 C5 C6 121.3(5) . . ?
C4 C5 C7 117.3(4) . . ?
C10 C4 C3 121.1(4) . . ?
C10 C4 C5 120.2(5) . . ?
C5 C4 C3 118.6(4) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 C9 119.5(5) . . ?
C7 C8 H8 120.2 . . ?
C21 C20 C19 118.4(5) . . ?
C21 C20 C23 121.7(5) . . ?
C19 C20 C23 119.9(6) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(6) . . ?
C14 C13 H13 119.6 . . ?
C16 C15 H15 120.2 . . ?
C16 C15 C14 119.5(6) . . ?
C14 C15 H15 120.2 . . ?
C13 C14 C15 120.3(5) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C22 C21 H21 118.9 . . ?
C20 C21 C22 122.2(5) . . ?
C20 C21 H21 118.9 . . ?
C18 C19 C20 120.6(6) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
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 . . ?
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 O1 1.449(4) . ?
S1 O2 1.438(4) . ?
S1 C17 1.764(5) . ?
S1 C1 1.785(5) . ?
O3 H3 0.8200 . ?
O3 C3 1.357(5) . ?
C17 C18 1.385(9) . ?
C17 C22 1.389(7) . ?
C10 H10 0.9300 . ?
C10 C9 1.359(8) . ?
C10 C4 1.399(6) . ?
C16 H16 0.9300 . ?
C16 C11 1.401(8) . ?
C16 C15 1.379(7) . ?
C11 C6 1.500(6) . ?
C11 C12 1.396(8) . ?
C6 C1 1.381(8) . ?
C6 C5 1.430(6) . ?
C9 H9 0.9300 . ?
C9 C8 1.412(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(8) . ?
C2 H2 0.9300 . ?
C2 C1 1.415(6) . ?
C2 C3 1.362(6) . ?
C7 H7 0.9300 . ?
C7 C5 1.423(8) . ?
C7 C8 1.369(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(7) . ?
C3 C4 1.430(8) . ?
C22 H22 0.9300 . ?
C22 C21 1.378(8) . ?
C5 C4 1.421(6) . ?
C8 H8 0.9300 . ?
C20 C21 1.372(9) . ?
C20 C19 1.393(7) . ?
C20 C23 1.499(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(9) . ?
C15 H15 0.9300 . ?
C15 C14 1.381(9) . ?
C14 H14 0.9300 . ?
C21 H21 0.9300 . ?
C19 H19 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
