#------------------------------------------------------------------------------
#$Date: 2020-05-17 02:33:33 +0300 (Sun, 17 May 2020) $
#$Revision: 252123 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038381.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_4038381
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            'C17 H16 O4 S'
_chemical_formula_weight         316.36
_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                85.8850(10)
_cell_angle_beta                 73.7530(10)
_cell_angle_gamma                86.5520(10)
_cell_formula_units_Z            2
_cell_length_a                   8.5546(2)
_cell_length_b                   9.0687(2)
_cell_length_c                   9.9760(2)
_cell_measurement_reflns_used    8575
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3675
_cell_measurement_theta_min      2.2535
_cell_volume                     740.46(3)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0205
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15867
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.410
_diffrn_reflns_theta_min         2.254
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0312
_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)+(0.0431P)²+0.4445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2743
_reflns_number_total             3025
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00035_si_001.cif
_cod_data_source_block           mo_180844LT_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               4038381
_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 0.55538(4) 0.67399(4) 0.77229(3) 0.01462(11) Uani 1 1 d . . . . .
O1 O -0.40066(12) 0.70893(11) 1.24824(11) 0.0204(2) Uani 1 1 d . . . . .
O2 O -0.17795(12) 0.54038(11) 1.31213(10) 0.0184(2) Uani 1 1 d . . . . .
O3 O 0.65444(12) 0.56406(12) 0.82619(11) 0.0228(2) Uani 1 1 d . . . . .
O4 O 0.60795(12) 0.82404(11) 0.75038(11) 0.0203(2) Uani 1 1 d . . . . .
C1 C 0.53793(18) 0.61419(16) 0.61326(14) 0.0189(3) Uani 1 1 d . . . . .
H1 H 0.6447 0.6157 0.5438 0.028 Uiso 1 1 calc R U . . .
H3 H 0.4603 0.6803 0.5797 0.028 Uiso 1 1 calc R U . . .
H16 H 0.4991 0.5132 0.6278 0.028 Uiso 1 1 calc R U . . .
C2 C 0.36025(16) 0.66620(15) 0.88844(14) 0.0143(3) Uani 1 1 d . . . . .
H15 H 0.3474 0.5938 0.9640 0.017 Uiso 1 1 calc R U . . .
C3 C 0.22623(16) 0.74938(15) 0.88454(14) 0.0136(3) Uani 1 1 d . . . . .
C4 C 0.06848(16) 0.72611(15) 0.99019(14) 0.0140(3) Uani 1 1 d . . . . .
C5 C 0.03282(16) 0.62937(15) 1.10872(14) 0.0147(3) Uani 1 1 d . . . . .
H4 H 0.1154 0.5661 1.1315 0.018 Uiso 1 1 calc R U . . .
C6 C -0.12632(17) 0.62822(15) 1.19213(14) 0.0150(3) Uani 1 1 d . . . . .
C7 C -0.24937(16) 0.72146(15) 1.15691(15) 0.0160(3) Uani 1 1 d . . . . .
C8 C -0.53115(17) 0.79628(18) 1.21548(17) 0.0238(3) Uani 1 1 d . . . . .
H9 H -0.5083 0.9014 1.2113 0.036 Uiso 1 1 calc R U . . .
H8 H -0.6330 0.7769 1.2879 0.036 Uiso 1 1 calc R U . . .
H2 H -0.5416 0.7705 1.1247 0.036 Uiso 1 1 calc R U . . .
C9 C -0.05808(18) 0.44087(16) 1.34724(15) 0.0191(3) Uani 1 1 d . . . . .
H6 H -0.0095 0.3778 1.2692 0.029 Uiso 1 1 calc R U . . .
H7 H -0.1094 0.3790 1.4309 0.029 Uiso 1 1 calc R U . . .
H5 H 0.0270 0.4974 1.3658 0.029 Uiso 1 1 calc R U . . .
C10 C -0.21279(17) 0.81606(15) 1.03816(15) 0.0163(3) Uani 1 1 d . . . . .
H14 H -0.2952 0.8782 1.0137 0.020 Uiso 1 1 calc R U . . .
C11 C -0.05206(17) 0.81784(15) 0.95546(14) 0.0147(3) Uani 1 1 d . . . . .
C12 C 0.02288(17) 0.90582(15) 0.82677(14) 0.0151(3) Uani 1 1 d . . . . .
C13 C 0.19180(16) 0.86785(15) 0.78403(14) 0.0142(3) Uani 1 1 d . . . . .
C14 C 0.28977(17) 0.93787(15) 0.66438(15) 0.0169(3) Uani 1 1 d . . . . .
H13 H 0.4037 0.9153 0.6357 0.020 Uiso 1 1 calc R U . . .
C15 C 0.21889(18) 1.04191(16) 0.58671(15) 0.0198(3) Uani 1 1 d . . . . .
H12 H 0.2849 1.0891 0.5038 0.024 Uiso 1 1 calc R U . . .
C16 C 0.05300(19) 1.07711(16) 0.62932(16) 0.0210(3) Uani 1 1 d . . . . .
H11 H 0.0068 1.1483 0.5753 0.025 Uiso 1 1 calc R U . . .
C17 C -0.04649(18) 1.00963(16) 0.74997(15) 0.0188(3) Uani 1 1 d . . . . .
H10 H -0.1600 1.0344 0.7791 0.023 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 O4 117.73(6) . . ?
O3 S1 C2 105.82(6) . . ?
O4 S1 C2 110.36(6) . . ?
O3 S1 C1 107.51(7) . . ?
O4 S1 C1 108.90(7) . . ?
C2 S1 C1 105.85(7) . . ?
C7 O1 C8 117.21(11) . . ?
C6 O2 C9 116.25(11) . . ?
S1 C1 H1 109.5 . . ?
S1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
S1 C1 H16 109.5 . . ?
H1 C1 H16 109.5 . . ?
H3 C1 H16 109.5 . . ?
C3 C2 S1 128.30(11) . . ?
C3 C2 H15 115.8 . . ?
S1 C2 H15 115.8 . . ?
C2 C3 C4 121.45(12) . . ?
C2 C3 C13 133.14(13) . . ?
C4 C3 C13 105.32(11) . . ?
C11 C4 C5 121.26(12) . . ?
C11 C4 C3 109.68(12) . . ?
C5 C4 C3 129.06(12) . . ?
C6 C5 C4 118.03(13) . . ?
C6 C5 H4 121.0 . . ?
C4 C5 H4 121.0 . . ?
O2 C6 C5 124.21(13) . . ?
O2 C6 C7 114.97(12) . . ?
C5 C6 C7 120.81(13) . . ?
O1 C7 C10 124.75(13) . . ?
O1 C7 C6 114.62(12) . . ?
C10 C7 C6 120.63(12) . . ?
O1 C8 H9 109.5 . . ?
O1 C8 H8 109.5 . . ?
H9 C8 H8 109.5 . . ?
O1 C8 H2 109.5 . . ?
H9 C8 H2 109.5 . . ?
H8 C8 H2 109.5 . . ?
O2 C9 H6 109.5 . . ?
O2 C9 H7 109.5 . . ?
H6 C9 H7 109.5 . . ?
O2 C9 H5 109.5 . . ?
H6 C9 H5 109.5 . . ?
H7 C9 H5 109.5 . . ?
C7 C10 C11 118.27(13) . . ?
C7 C10 H14 120.9 . . ?
C11 C10 H14 120.9 . . ?
C4 C11 C10 120.99(13) . . ?
C4 C11 C12 108.36(12) . . ?
C10 C11 C12 130.65(13) . . ?
C17 C12 C13 121.07(13) . . ?
C17 C12 C11 130.19(13) . . ?
C13 C12 C11 108.74(12) . . ?
C14 C13 C12 119.47(13) . . ?
C14 C13 C3 132.65(13) . . ?
C12 C13 C3 107.86(12) . . ?
C13 C14 C15 119.20(13) . . ?
C13 C14 H13 120.4 . . ?
C15 C14 H13 120.4 . . ?
C16 C15 C14 120.65(13) . . ?
C16 C15 H12 119.7 . . ?
C14 C15 H12 119.7 . . ?
C15 C16 C17 120.89(14) . . ?
C15 C16 H11 119.6 . . ?
C17 C16 H11 119.6 . . ?
C12 C17 C16 118.70(13) . . ?
C12 C17 H10 120.7 . . ?
C16 C17 H10 120.7 . . ?
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 1.4414(11) . ?
S1 O4 1.4414(11) . ?
S1 C2 1.7476(14) . ?
S1 C1 1.7605(14) . ?
O1 C7 1.3642(16) . ?
O1 C8 1.4287(17) . ?
O2 C6 1.3683(17) . ?
O2 C9 1.4258(17) . ?
C1 H1 0.9800 . ?
C1 H3 0.9800 . ?
C1 H16 0.9800 . ?
C2 C3 1.3423(19) . ?
C2 H15 0.9500 . ?
C3 C4 1.4775(18) . ?
C3 C13 1.4897(18) . ?
C4 C11 1.3895(19) . ?
C4 C5 1.3937(19) . ?
C5 C6 1.3829(19) . ?
C5 H4 0.9500 . ?
C6 C7 1.4156(19) . ?
C7 C10 1.384(2) . ?
C8 H9 0.9800 . ?
C8 H8 0.9800 . ?
C8 H2 0.9800 . ?
C9 H6 0.9800 . ?
C9 H7 0.9800 . ?
C9 H5 0.9800 . ?
C10 C11 1.3919(19) . ?
C10 H14 0.9500 . ?
C11 C12 1.4662(19) . ?
C12 C17 1.3817(19) . ?
C12 C13 1.4159(19) . ?
C13 C14 1.388(2) . ?
C14 C15 1.395(2) . ?
C14 H13 0.9500 . ?
C15 C16 1.387(2) . ?
C15 H12 0.9500 . ?
C16 C17 1.390(2) . ?
C16 H11 0.9500 . ?
C17 H10 0.9500 . ?
