#------------------------------------------------------------------------------
#$Date: 2020-05-17 02:33:33 +0300 (Sun, 17 May 2020) $
#$Revision: 252123 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038380.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_4038380
loop_
_publ_author_name
'Chang, Meng-Yang'
'Tsai, Yu-Lin'
'Chen, Hsing-Yin'
_publ_section_title
;
 CuBr₂-Mediated One-Pot Synthesis of Sulfonyl
 9-Fluorenylidenes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00035
_journal_year                    2020
_chemical_formula_sum            'C23 H22 O5 S'
_chemical_formula_weight         410.46
_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_method           SHELXL-2014/6
_cell_angle_alpha                81.239(6)
_cell_angle_beta                 78.859(6)
_cell_angle_gamma                75.503(6)
_cell_formula_units_Z            2
_cell_length_a                   7.9278(10)
_cell_length_b                   8.4094(10)
_cell_length_c                   15.9103(19)
_cell_measurement_reflns_used    8757
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3880
_cell_measurement_theta_min      2.5167
_cell_volume                     1001.5(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15223
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.461
_diffrn_reflns_theta_min         1.312
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.8375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lump
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0354
_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)+(0.0454P)²+0.4731P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3667
_reflns_number_total             4082
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00035_si_001.cif
_cod_data_source_block           180611LT_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4038380
_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.
;
_shelxl_version_number           2014/6
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 0.31039(4) 0.77912(4) 0.81685(2) 0.01820(11) Uani 1 1 d . . . . .
O1 O 0.74910(14) 1.20523(12) 0.47306(7) 0.0222(2) Uani 1 1 d . . . . .
O2 O 0.18742(14) 0.93742(14) 0.81496(7) 0.0278(3) Uani 1 1 d . . . . .
O3 O 0.24771(14) 0.63312(14) 0.85286(7) 0.0257(3) Uani 1 1 d . . . . .
O4 O 0.43986(13) 0.48443(13) 0.67558(7) 0.0238(2) Uani 1 1 d . . . . .
O5 O 0.69720(14) 0.94622(12) 0.42528(7) 0.0202(2) Uani 1 1 d . . . . .
C1 C 0.8923(2) 0.8147(2) 1.00429(11) 0.0336(4) Uani 1 1 d . . . . .
H22 H 0.9475 0.7033 1.0279 0.050 Uiso 1 1 calc R U . . .
H3 H 0.8419 0.8839 1.0514 0.050 Uiso 1 1 calc R U . . .
H1 H 0.9813 0.8629 0.9642 0.050 Uiso 1 1 calc R U . . .
C2 C 0.7482(2) 0.8052(2) 0.95730(10) 0.0247(3) Uani 1 1 d . . . . .
C3 C 0.6990(2) 0.6571(2) 0.95924(10) 0.0254(3) Uani 1 1 d . . . . .
H4 H 0.7578 0.5603 0.9904 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5656(2) 0.64820(19) 0.91647(10) 0.0226(3) Uani 1 1 d . . . . .
H5 H 0.5332 0.5463 0.9181 0.027 Uiso 1 1 calc R U . . .
C5 C 0.48004(18) 0.78996(18) 0.87119(9) 0.0182(3) Uani 1 1 d . . . . .
C6 C 0.41288(18) 0.75575(17) 0.70776(9) 0.0167(3) Uani 1 1 d . . . . .
H6 H 0.3212 0.7883 0.6701 0.020 Uiso 1 1 calc R U . . .
H7 H 0.4949 0.8307 0.6896 0.020 Uiso 1 1 calc R U . . .
C7 C 0.51421(18) 0.57932(17) 0.69622(9) 0.0165(3) Uani 1 1 d . . . . .
C8 C 0.69610(18) 0.52072(17) 0.71804(9) 0.0163(3) Uani 1 1 d . . . . .
C9 C 0.82525(18) 0.61541(17) 0.69908(9) 0.0169(3) Uani 1 1 d . . . . .
C10 C 0.80597(17) 0.77323(17) 0.64163(9) 0.0167(3) Uani 1 1 d . . . . .
C11 C 0.84253(19) 0.91192(18) 0.66516(10) 0.0197(3) Uani 1 1 d . . . . .
H17 H 0.8801 0.9065 0.7189 0.024 Uiso 1 1 calc R U . . .
C12 C 0.82443(19) 1.05885(18) 0.61039(10) 0.0201(3) Uani 1 1 d . . . . .
H18 H 0.8476 1.1536 0.6276 0.024 Uiso 1 1 calc R U . . .
C13 C 0.77311(18) 1.06791(17) 0.53125(9) 0.0178(3) Uani 1 1 d . . . . .
C14 C 0.7687(2) 1.35461(17) 0.49845(11) 0.0233(3) Uani 1 1 d . . . . .
H15 H 0.6865 1.3804 0.5517 0.035 Uiso 1 1 calc R U . . .
H16 H 0.7429 1.4452 0.4528 0.035 Uiso 1 1 calc R U . . .
H2 H 0.8900 1.3408 0.5083 0.035 Uiso 1 1 calc R U . . .
C15 C 0.98272(19) 0.55187(19) 0.73135(10) 0.0222(3) Uani 1 1 d . . . . .
H11 H 1.0699 0.6153 0.7203 0.027 Uiso 1 1 calc R U . . .
C16 C 1.0155(2) 0.3987(2) 0.77911(10) 0.0255(3) Uani 1 1 d . . . . .
H10 H 1.1231 0.3593 0.8014 0.031 Uiso 1 1 calc R U . . .
C17 C 0.8912(2) 0.30263(19) 0.79444(10) 0.0244(3) Uani 1 1 d . . . . .
H9 H 0.9150 0.1957 0.8254 0.029 Uiso 1 1 calc R U . . .
C18 C 0.73272(19) 0.36402(18) 0.76420(10) 0.0204(3) Uani 1 1 d . . . . .
H8 H 0.6473 0.2987 0.7749 0.025 Uiso 1 1 calc R U . . .
C19 C 0.75596(17) 0.78197(17) 0.56074(9) 0.0161(3) Uani 1 1 d . . . . .
H19 H 0.7322 0.6872 0.5439 0.019 Uiso 1 1 calc R U . . .
C20 C 0.74085(18) 0.92618(17) 0.50546(9) 0.0163(3) Uani 1 1 d . . . . .
C21 C 0.6803(2) 0.80258(18) 0.39320(10) 0.0239(3) Uani 1 1 d . . . . .
H12 H 0.7911 0.7185 0.3930 0.036 Uiso 1 1 calc R U . . .
H14 H 0.6539 0.8315 0.3344 0.036 Uiso 1 1 calc R U . . .
H13 H 0.5843 0.7591 0.4302 0.036 Uiso 1 1 calc R U . . .
C22 C 0.5267(2) 0.93952(19) 0.86819(10) 0.0234(3) Uani 1 1 d . . . . .
H21 H 0.4680 1.0361 0.8368 0.028 Uiso 1 1 calc R U . . .
C23 C 0.6597(2) 0.9460(2) 0.91153(11) 0.0267(3) Uani 1 1 d . . . . .
H20 H 0.6913 1.0482 0.9101 0.032 Uiso 1 1 calc R U . . .
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
O3 S1 O2 119.44(7) . . ?
O3 S1 C5 108.38(7) . . ?
O2 S1 C5 108.05(7) . . ?
O3 S1 C6 108.59(7) . . ?
O2 S1 C6 106.07(7) . . ?
C5 S1 C6 105.47(7) . . ?
C13 O1 C14 116.96(11) . . ?
C20 O5 C21 117.03(11) . . ?
C2 C1 H22 109.5 . . ?
C2 C1 H3 109.5 . . ?
H22 C1 H3 109.5 . . ?
C2 C1 H1 109.5 . . ?
H22 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
C3 C2 C23 118.53(14) . . ?
C3 C2 C1 120.99(15) . . ?
C23 C2 C1 120.48(15) . . ?
C4 C3 C2 121.12(15) . . ?
C4 C3 H4 119.4 . . ?
C2 C3 H4 119.4 . . ?
C3 C4 C5 119.18(14) . . ?
C3 C4 H5 120.4 . . ?
C5 C4 H5 120.4 . . ?
C4 C5 C22 120.87(14) . . ?
C4 C5 S1 119.29(11) . . ?
C22 C5 S1 119.84(11) . . ?
C7 C6 S1 112.09(10) . . ?
C7 C6 H6 109.2 . . ?
S1 C6 H6 109.2 . . ?
C7 C6 H7 109.2 . . ?
S1 C6 H7 109.2 . . ?
H6 C6 H7 107.9 . . ?
O4 C7 C8 120.95(13) . . ?
O4 C7 C6 118.95(12) . . ?
C8 C7 C6 119.86(12) . . ?
C18 C8 C9 119.65(13) . . ?
C18 C8 C7 115.86(12) . . ?
C9 C8 C7 124.41(12) . . ?
C15 C9 C8 118.12(13) . . ?
C15 C9 C10 118.68(12) . . ?
C8 C9 C10 123.07(12) . . ?
C11 C10 C19 119.04(13) . . ?
C11 C10 C9 121.08(13) . . ?
C19 C10 C9 119.85(12) . . ?
C10 C11 C12 120.37(13) . . ?
C10 C11 H17 119.8 . . ?
C12 C11 H17 119.8 . . ?
C13 C12 C11 120.53(13) . . ?
C13 C12 H18 119.7 . . ?
C11 C12 H18 119.7 . . ?
O1 C13 C12 125.60(13) . . ?
O1 C13 C20 114.80(12) . . ?
C12 C13 C20 119.60(13) . . ?
O1 C14 H15 109.5 . . ?
O1 C14 H16 109.5 . . ?
H15 C14 H16 109.5 . . ?
O1 C14 H2 109.5 . . ?
H15 C14 H2 109.5 . . ?
H16 C14 H2 109.5 . . ?
C16 C15 C9 121.70(14) . . ?
C16 C15 H11 119.2 . . ?
C9 C15 H11 119.2 . . ?
C15 C16 C17 120.02(14) . . ?
C15 C16 H10 120.0 . . ?
C17 C16 H10 120.0 . . ?
C18 C17 C16 119.36(14) . . ?
C18 C17 H9 120.3 . . ?
C16 C17 H9 120.3 . . ?
C17 C18 C8 121.06(14) . . ?
C17 C18 H8 119.5 . . ?
C8 C18 H8 119.5 . . ?
C20 C19 C10 120.93(12) . . ?
C20 C19 H19 119.5 . . ?
C10 C19 H19 119.5 . . ?
O5 C20 C19 125.43(12) . . ?
O5 C20 C13 115.09(12) . . ?
C19 C20 C13 119.48(13) . . ?
O5 C21 H12 109.5 . . ?
O5 C21 H14 109.5 . . ?
H12 C21 H14 109.5 . . ?
O5 C21 H13 109.5 . . ?
H12 C21 H13 109.5 . . ?
H14 C21 H13 109.5 . . ?
C23 C22 C5 119.08(14) . . ?
C23 C22 H21 120.5 . . ?
C5 C22 H21 120.5 . . ?
C22 C23 C2 121.22(14) . . ?
C22 C23 H20 119.4 . . ?
C2 C23 H20 119.4 . . ?
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 O3 1.4366(11) . ?
S1 O2 1.4397(11) . ?
S1 C5 1.7606(15) . ?
S1 C6 1.7862(14) . ?
O1 C13 1.3636(17) . ?
O1 C14 1.4289(16) . ?
O4 C7 1.2174(17) . ?
O5 C20 1.3607(17) . ?
O5 C21 1.4258(17) . ?
C1 C2 1.504(2) . ?
C1 H22 0.9800 . ?
C1 H3 0.9800 . ?
C1 H1 0.9800 . ?
C2 C3 1.390(2) . ?
C2 C23 1.394(2) . ?
C3 C4 1.386(2) . ?
C3 H4 0.9500 . ?
C4 C5 1.387(2) . ?
C4 H5 0.9500 . ?
C5 C22 1.389(2) . ?
C6 C7 1.5197(19) . ?
C6 H6 0.9900 . ?
C6 H7 0.9900 . ?
C7 C8 1.4927(19) . ?
C8 C18 1.399(2) . ?
C8 C9 1.4103(19) . ?
C9 C15 1.392(2) . ?
C9 C10 1.484(2) . ?
C10 C11 1.3887(19) . ?
C10 C19 1.405(2) . ?
C11 C12 1.392(2) . ?
C11 H17 0.9500 . ?
C12 C13 1.382(2) . ?
C12 H18 0.9500 . ?
C13 C20 1.4129(19) . ?
C14 H15 0.9800 . ?
C14 H16 0.9800 . ?
C14 H2 0.9800 . ?
C15 C16 1.384(2) . ?
C15 H11 0.9500 . ?
C16 C17 1.389(2) . ?
C16 H10 0.9500 . ?
C17 C18 1.382(2) . ?
C17 H9 0.9500 . ?
C18 H8 0.9500 . ?
C19 C20 1.379(2) . ?
C19 H19 0.9500 . ?
C21 H12 0.9800 . ?
C21 H14 0.9800 . ?
C21 H13 0.9800 . ?
C22 C23 1.382(2) . ?
C22 H21 0.9500 . ?
C23 H20 0.9500 . ?
