#------------------------------------------------------------------------------
#$Date: 2020-05-17 02:33:33 +0300 (Sun, 17 May 2020) $
#$Revision: 252123 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038383.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_4038383
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            'C24 H22 O5 S'
_chemical_formula_weight         422.47
_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                98.226(3)
_cell_angle_beta                 101.267(3)
_cell_angle_gamma                117.085(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4622(6)
_cell_length_b                   9.7507(6)
_cell_length_c                   13.1691(10)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.4091
_cell_measurement_theta_min      2.4889
_cell_volume                     1022.78(13)
_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 0.981
_diffrn_measured_fraction_theta_max 0.971
_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  0.0551
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30196
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.507
_diffrn_reflns_theta_min         1.636
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lump
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0617
_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)+(0.0638P)²+1.3017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1696
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3398
_reflns_number_total             4125
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00035_si_001.cif
_cod_data_source_block           180907LT_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_original_cell_volume        1022.78(12)
_cod_database_code               4038383
_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 0.41649(8) 0.34714(8) 0.16546(5) 0.0280(2) Uani 1 1 d . . . . .
O1 O 0.8473(2) 1.3184(2) 0.43009(16) 0.0316(5) Uani 1 1 d . . . . .
O2 O 0.3691(3) 0.2609(2) 0.24394(17) 0.0368(5) Uani 1 1 d . . . . .
O3 O 0.2863(2) 0.3243(3) 0.07601(17) 0.0373(5) Uani 1 1 d . . . . .
O4 O 0.8644(2) 0.8561(2) 0.28548(15) 0.0299(5) Uani 1 1 d . . . . .
O5 O 1.0133(2) 1.1861(2) 0.36345(16) 0.0331(5) Uani 1 1 d . . . . .
C1 C 0.7590(4) 1.3982(3) 0.4546(2) 0.0325(6) Uani 1 1 d . . . . .
H14 H 0.6729 1.3766 0.3896 0.049 Uiso 1 1 calc R U . . .
H1 H 0.8364 1.5135 0.4813 0.049 Uiso 1 1 calc R U . . .
H13 H 0.7071 1.3593 0.5097 0.049 Uiso 1 1 calc R U . . .
C2 C 0.7601(3) 1.1575(3) 0.3915(2) 0.0251(6) Uani 1 1 d . . . . .
C3 C 0.8513(3) 1.0880(3) 0.3593(2) 0.0269(6) Uani 1 1 d . . . . .
C4 C 0.7744(3) 0.9238(3) 0.3167(2) 0.0248(6) Uani 1 1 d . . . . .
C5 C 0.6085(3) 0.8282(3) 0.3088(2) 0.0249(6) Uani 1 1 d . . . . .
C6 C 0.4958(3) 0.6537(3) 0.2655(2) 0.0254(6) Uani 1 1 d . . . . .
C7 C 0.5435(3) 0.5521(3) 0.2271(2) 0.0294(6) Uani 1 1 d . . . . .
H6 H 0.6585 0.5959 0.2341 0.035 Uiso 1 1 calc R U . . .
C8 C 0.5507(3) 0.2996(3) 0.1145(2) 0.0281(6) Uani 1 1 d . . . . .
C9 C 0.5731(3) 0.1763(3) 0.1405(2) 0.0293(6) Uani 1 1 d . . . . .
H5 H 0.5214 0.1229 0.1889 0.035 Uiso 1 1 calc R U . . .
C10 C 0.6711(4) 0.1320(4) 0.0954(2) 0.0336(7) Uani 1 1 d . . . . .
H4 H 0.6855 0.0472 0.1131 0.040 Uiso 1 1 calc R U . . .
C11 C 0.7483(4) 0.2078(4) 0.0254(2) 0.0367(7) Uani 1 1 d . . . . .
C12 C 0.8547(4) 0.1597(5) -0.0234(3) 0.0527(10) Uani 1 1 d . . . . .
H3 H 0.9718 0.2420 0.0092 0.079 Uiso 1 1 calc R U . . .
H22 H 0.8237 0.1480 -0.1009 0.079 Uiso 1 1 calc R U . . .
H2 H 0.8384 0.0578 -0.0104 0.079 Uiso 1 1 calc R U . . .
C13 C 0.3313(3) 0.6272(3) 0.2741(2) 0.0250(6) Uani 1 1 d . . . . .
C14 C 0.3469(3) 0.7753(3) 0.3164(2) 0.0245(6) Uani 1 1 d . . . . .
C15 C 0.5197(3) 0.9006(3) 0.3393(2) 0.0237(6) Uani 1 1 d . . . . .
C16 C 0.9023(5) 0.8838(5) 0.1875(3) 0.0510(9) Uani 1 1 d . . . . .
H9 H 0.7994 0.8474 0.1306 0.076 Uiso 1 1 calc R U . . .
H8 H 0.9571 0.8245 0.1667 0.076 Uiso 1 1 calc R U . . .
H7 H 0.9764 0.9982 0.1982 0.076 Uiso 1 1 calc R U . . .
C17 C 1.1346(4) 1.1818(4) 0.4439(3) 0.0399(7) Uani 1 1 d . . . . .
H12 H 1.1262 1.2168 0.5149 0.060 Uiso 1 1 calc R U . . .
H11 H 1.2457 1.2530 0.4396 0.060 Uiso 1 1 calc R U . . .
H10 H 1.1155 1.0724 0.4325 0.060 Uiso 1 1 calc R U . . .
C18 C 0.5930(3) 1.0639(3) 0.3811(2) 0.0254(6) Uani 1 1 d . . . . .
H15 H 0.5306 1.1103 0.4021 0.030 Uiso 1 1 calc R U . . .
C19 C 0.2119(3) 0.7873(3) 0.3314(2) 0.0281(6) Uani 1 1 d . . . . .
H19 H 0.2225 0.8883 0.3584 0.034 Uiso 1 1 calc R U . . .
C20 C 0.0605(3) 0.6475(4) 0.3058(2) 0.0334(7) Uani 1 1 d . . . . .
H18 H -0.0339 0.6528 0.3155 0.040 Uiso 1 1 calc R U . . .
C21 C 0.0453(3) 0.5013(3) 0.2666(2) 0.0307(6) Uani 1 1 d . . . . .
H17 H -0.0593 0.4071 0.2506 0.037 Uiso 1 1 calc R U . . .
C22 C 0.1793(3) 0.4891(3) 0.2502(2) 0.0292(6) Uani 1 1 d . . . . .
H16 H 0.1674 0.3875 0.2229 0.035 Uiso 1 1 calc R U . . .
C23 C 0.6273(4) 0.3773(4) 0.0443(2) 0.0363(7) Uani 1 1 d . . . . .
H20 H 0.6119 0.4614 0.0261 0.044 Uiso 1 1 calc R U . . .
C24 C 0.7254(4) 0.3325(4) 0.0011(2) 0.0396(7) Uani 1 1 d . . . . .
H21 H 0.7789 0.3873 -0.0462 0.048 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
O2 S1 O3 117.69(13) . . ?
O2 S1 C8 108.76(13) . . ?
O3 S1 C8 107.90(13) . . ?
O2 S1 C7 110.53(13) . . ?
O3 S1 C7 108.64(13) . . ?
C8 S1 C7 102.16(13) . . ?
C2 O1 C1 117.9(2) . . ?
C4 O4 C16 113.8(2) . . ?
C3 O5 C17 115.2(2) . . ?
O1 C1 H14 109.5 . . ?
O1 C1 H1 109.5 . . ?
H14 C1 H1 109.5 . . ?
O1 C1 H13 109.5 . . ?
H14 C1 H13 109.5 . . ?
H1 C1 H13 109.5 . . ?
O1 C2 C18 124.4(2) . . ?
O1 C2 C3 114.9(2) . . ?
C18 C2 C3 120.7(2) . . ?
O5 C3 C4 120.8(2) . . ?
O5 C3 C2 118.8(2) . . ?
C4 C3 C2 120.2(2) . . ?
O4 C4 C5 120.2(2) . . ?
O4 C4 C3 120.0(2) . . ?
C5 C4 C3 119.7(2) . . ?
C4 C5 C15 118.9(2) . . ?
C4 C5 C6 131.3(2) . . ?
C15 C5 C6 109.6(2) . . ?
C7 C6 C5 123.8(2) . . ?
C7 C6 C13 131.4(3) . . ?
C5 C6 C13 104.8(2) . . ?
C6 C7 S1 127.0(2) . . ?
C6 C7 H6 116.5 . . ?
S1 C7 H6 116.5 . . ?
C23 C8 C9 119.8(3) . . ?
C23 C8 S1 120.8(2) . . ?
C9 C8 S1 119.3(2) . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H5 120.2 . . ?
C8 C9 H5 120.2 . . ?
C11 C10 C9 121.5(3) . . ?
C11 C10 H4 119.2 . . ?
C9 C10 H4 119.2 . . ?
C10 C11 C24 118.0(3) . . ?
C10 C11 C12 121.5(3) . . ?
C24 C11 C12 120.4(3) . . ?
C11 C12 H3 109.5 . . ?
C11 C12 H22 109.5 . . ?
H3 C12 H22 109.5 . . ?
C11 C12 H2 109.5 . . ?
H3 C12 H2 109.5 . . ?
H22 C12 H2 109.5 . . ?
C22 C13 C14 119.6(3) . . ?
C22 C13 C6 131.8(3) . . ?
C14 C13 C6 108.6(2) . . ?
C19 C14 C13 121.3(2) . . ?
C19 C14 C15 129.6(3) . . ?
C13 C14 C15 109.1(2) . . ?
C18 C15 C5 122.4(2) . . ?
C18 C15 C14 129.7(2) . . ?
C5 C15 C14 107.9(2) . . ?
O4 C16 H9 109.5 . . ?
O4 C16 H8 109.5 . . ?
H9 C16 H8 109.5 . . ?
O4 C16 H7 109.5 . . ?
H9 C16 H7 109.5 . . ?
H8 C16 H7 109.5 . . ?
O5 C17 H12 109.5 . . ?
O5 C17 H11 109.5 . . ?
H12 C17 H11 109.5 . . ?
O5 C17 H10 109.5 . . ?
H12 C17 H10 109.5 . . ?
H11 C17 H10 109.5 . . ?
C15 C18 C2 118.0(2) . . ?
C15 C18 H15 121.0 . . ?
C2 C18 H15 121.0 . . ?
C14 C19 C20 118.0(3) . . ?
C14 C19 H19 121.0 . . ?
C20 C19 H19 121.0 . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H18 119.5 . . ?
C19 C20 H18 119.5 . . ?
C20 C21 C22 121.2(3) . . ?
C20 C21 H17 119.4 . . ?
C22 C21 H17 119.4 . . ?
C21 C22 C13 118.9(3) . . ?
C21 C22 H16 120.5 . . ?
C13 C22 H16 120.5 . . ?
C24 C23 C8 119.8(3) . . ?
C24 C23 H20 120.1 . . ?
C8 C23 H20 120.1 . . ?
C23 C24 C11 121.3(3) . . ?
C23 C24 H21 119.4 . . ?
C11 C24 H21 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 O2 1.436(2) . ?
S1 O3 1.437(2) . ?
S1 C8 1.748(3) . ?
S1 C7 1.750(3) . ?
O1 C2 1.353(3) . ?
O1 C1 1.425(3) . ?
O4 C4 1.379(3) . ?
O4 C16 1.435(4) . ?
O5 C3 1.373(3) . ?
O5 C17 1.422(4) . ?
C1 H14 0.9800 . ?
C1 H1 0.9800 . ?
C1 H13 0.9800 . ?
C2 C18 1.385(4) . ?
C2 C3 1.405(4) . ?
C3 C4 1.390(4) . ?
C4 C5 1.386(4) . ?
C5 C15 1.399(4) . ?
C5 C6 1.479(4) . ?
C6 C7 1.340(4) . ?
C6 C13 1.487(4) . ?
C7 H6 0.9500 . ?
C8 C23 1.384(4) . ?
C8 C9 1.389(4) . ?
C9 C10 1.380(4) . ?
C9 H5 0.9500 . ?
C10 C11 1.377(4) . ?
C10 H4 0.9500 . ?
C11 C24 1.396(5) . ?
C11 C12 1.498(4) . ?
C12 H3 0.9800 . ?
C12 H22 0.9800 . ?
C12 H2 0.9800 . ?
C13 C22 1.386(4) . ?
C13 C14 1.401(4) . ?
C14 C19 1.383(4) . ?
C14 C15 1.463(4) . ?
C15 C18 1.383(4) . ?
C16 H9 0.9800 . ?
C16 H8 0.9800 . ?
C16 H7 0.9800 . ?
C17 H12 0.9800 . ?
C17 H11 0.9800 . ?
C17 H10 0.9800 . ?
C18 H15 0.9500 . ?
C19 C20 1.388(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(4) . ?
C20 H18 0.9500 . ?
C21 C22 1.380(4) . ?
C21 H17 0.9500 . ?
C22 H16 0.9500 . ?
C23 C24 1.372(4) . ?
C23 H20 0.9500 . ?
C24 H21 0.9500 . ?
