#------------------------------------------------------------------------------
#$Date: 2025-07-30 08:51:54 +0300 (Wed, 30 Jul 2025) $
#$Revision: 301408 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038388.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_4038388
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            'C16 H16 O2'
_chemical_formula_weight         240.28
_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                100.081(13)
_cell_angle_beta                 94.108(13)
_cell_angle_gamma                96.439(12)
_cell_formula_units_Z            4
_cell_length_a                   10.592(4)
_cell_length_b                   10.873(5)
_cell_length_c                   11.134(4)
_cell_measurement_reflns_used    5664
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      26.2578
_cell_measurement_theta_min      2.5515
_cell_volume                     1249.0(9)
_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      99(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_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  0.0764
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29295
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.602
_diffrn_reflns_theta_min         1.866
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabullar
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0837
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1286P)²+1.5710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2196
_refine_ls_wR_factor_ref         0.2436
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3540
_reflns_number_total             5145
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00035_si_001.cif
_cod_data_source_block           mo_181107lt_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 

2025-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32 H32 O4'
_cod_original_formula_weight         480.57
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1249.1(9)
_cod_database_code               4038388
_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
O1 O 0.2763(2) 0.3428(2) 0.1133(2) 0.0208(5) Uani 1 1 d . . . . .
O2 O 0.1996(2) 0.1077(2) 0.0893(2) 0.0244(6) Uani 1 1 d . . . . .
O3 O 0.1402(2) 0.6717(2) -0.0010(2) 0.0222(5) Uani 1 1 d . . . . .
O4 O 0.3777(2) 0.7459(2) 0.0621(2) 0.0245(6) Uani 1 1 d . . . . .
C1 C 0.3220(3) 0.4722(3) 0.1206(3) 0.0252(8) Uani 1 1 d . . . . .
H16 H 0.2583 0.5241 0.1540 0.038 Uiso 1 1 calc R U . . .
H3 H 0.3375 0.4880 0.0386 0.038 Uiso 1 1 calc R U . . .
H1 H 0.4018 0.4937 0.1743 0.038 Uiso 1 1 calc R U . . .
C2 C 0.2521(3) 0.3033(3) 0.2211(3) 0.0181(7) Uani 1 1 d . . . . .
C3 C 0.2652(3) 0.3804(3) 0.3359(3) 0.0198(7) Uani 1 1 d . . . . .
H7 H 0.2903 0.4684 0.3450 0.024 Uiso 1 1 calc R U . . .
C4 C 0.2406(3) 0.3258(3) 0.4379(3) 0.0200(7) Uani 1 1 d . . . . .
C5 C 0.2531(3) 0.3883(3) 0.5717(3) 0.0206(7) Uani 1 1 d . . . . .
H8 H 0.1890 0.4490 0.5852 0.025 Uiso 1 1 calc R U . . .
C6 C 0.2171(3) 0.2776(3) 0.6339(3) 0.0198(7) Uani 1 1 d . . . . .
C7 C 0.2126(3) 0.2751(3) 0.7563(3) 0.0222(7) Uani 1 1 d . . . . .
H12 H 0.2326 0.3504 0.8155 0.027 Uiso 1 1 calc R U . . .
C8 C 0.1783(3) 0.1604(3) 0.7928(3) 0.0260(8) Uani 1 1 d . . . . .
H2 H 0.1747 0.1576 0.8773 0.031 Uiso 1 1 calc R U . . .
C9 C 0.2103(3) 0.1736(3) 0.2073(3) 0.0186(7) Uani 1 1 d . . . . .
C10 C 0.1609(4) -0.0241(3) 0.0709(3) 0.0289(8) Uani 1 1 d . . . . .
H5 H 0.2211 -0.0631 0.1186 0.043 Uiso 1 1 calc R U . . .
H4 H 0.1596 -0.0604 -0.0163 0.043 Uiso 1 1 calc R U . . .
H6 H 0.0753 -0.0397 0.0976 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1848(3) 0.1197(3) 0.3084(3) 0.0186(7) Uani 1 1 d . . . . .
H15 H 0.1567 0.0322 0.2994 0.022 Uiso 1 1 calc R U . . .
C12 C 0.2017(3) 0.1976(3) 0.4240(3) 0.0184(7) Uani 1 1 d . . . . .
C13 C 0.1873(3) 0.1659(3) 0.5446(3) 0.0199(7) Uani 1 1 d . . . . .
C14 C 0.1532(3) 0.0514(3) 0.5822(3) 0.0227(7) Uani 1 1 d . . . . .
H14 H 0.1331 -0.0243 0.5236 0.027 Uiso 1 1 calc R U . . .
C15 C 0.1492(3) 0.0501(3) 0.7059(3) 0.0249(8) Uani 1 1 d . . . . .
H13 H 0.1262 -0.0274 0.7319 0.030 Uiso 1 1 calc R U . . .
C16 C 0.3870(3) 0.4569(3) 0.6177(3) 0.0244(8) Uani 1 1 d . . . . .
H11 H 0.3895 0.4929 0.7051 0.037 Uiso 1 1 calc R U . . .
H10 H 0.4073 0.5244 0.5717 0.037 Uiso 1 1 calc R U . . .
H9 H 0.4497 0.3971 0.6058 0.037 Uiso 1 1 calc R U . . .
C17 C 0.0047(3) 0.6536(3) -0.0273(3) 0.0250(8) Uani 1 1 d . . . . .
H20 H -0.0226 0.7265 -0.0578 0.037 Uiso 1 1 calc R U . . .
H17 H -0.0359 0.6443 0.0476 0.037 Uiso 1 1 calc R U . . .
H21 H -0.0205 0.5775 -0.0896 0.037 Uiso 1 1 calc R U . . .
C18 C 0.2094(3) 0.6996(3) -0.0946(3) 0.0183(7) Uani 1 1 d . . . . .
C19 C 0.1606(3) 0.6915(3) -0.2142(3) 0.0199(7) Uani 1 1 d . . . . .
H22 H 0.0729 0.6631 -0.2383 0.024 Uiso 1 1 calc R U . . .
C20 C 0.2423(3) 0.7256(3) -0.2999(3) 0.0205(7) Uani 1 1 d . . . . .
C21 C 0.2180(3) 0.7238(3) -0.4306(3) 0.0218(7) Uani 1 1 d . . . . .
C22 C 0.1070(3) 0.6893(3) -0.5099(3) 0.0261(8) Uani 1 1 d . . . . .
H23 H 0.0292 0.6595 -0.4809 0.031 Uiso 1 1 calc R U . . .
C23 C 0.1120(3) 0.6993(4) -0.6321(3) 0.0304(8) Uani 1 1 d . . . . .
H25 H 0.0369 0.6765 -0.6870 0.037 Uiso 1 1 calc R U . . .
C24 C 0.2262(4) 0.7424(3) -0.6751(3) 0.0295(8) Uani 1 1 d . . . . .
H18 H 0.2282 0.7493 -0.7588 0.035 Uiso 1 1 calc R U . . .
C25 C 0.5104(3) 0.7830(4) 0.1003(4) 0.0318(9) Uani 1 1 d . . . . .
H19 H 0.5611 0.7286 0.0490 0.048 Uiso 1 1 calc R U . . .
H31 H 0.5274 0.7750 0.1861 0.048 Uiso 1 1 calc R U . . .
H32 H 0.5337 0.8707 0.0920 0.048 Uiso 1 1 calc R U . . .
C26 C 0.3405(3) 0.7411(3) -0.0587(3) 0.0202(7) Uani 1 1 d . . . . .
C27 C 0.3708(3) 0.7673(3) -0.2632(3) 0.0231(7) Uani 1 1 d . . . . .
C28 C 0.4400(3) 0.8000(3) -0.3701(3) 0.0251(8) Uani 1 1 d . . . . .
H26 H 0.5081 0.7442 -0.3869 0.030 Uiso 1 1 calc R U . . .
C29 C 0.3334(3) 0.7667(3) -0.4740(3) 0.0240(7) Uani 1 1 d . . . . .
C30 C 0.3373(3) 0.7754(3) -0.5957(3) 0.0272(8) Uani 1 1 d . . . . .
H24 H 0.4152 0.8038 -0.6252 0.033 Uiso 1 1 calc R U . . .
C31 C 0.4979(3) 0.9376(3) -0.3498(4) 0.0301(8) Uani 1 1 d . . . . .
H28 H 0.4299 0.9916 -0.3408 0.045 Uiso 1 1 calc R U . . .
H27 H 0.5441 0.9525 -0.4201 0.045 Uiso 1 1 calc R U . . .
H29 H 0.5572 0.9570 -0.2753 0.045 Uiso 1 1 calc R U . . .
C32 C 0.4201(3) 0.7756(3) -0.1433(3) 0.0244(8) Uani 1 1 d . . . . .
H30 H 0.5077 0.8046 -0.1193 0.029 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'
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
C2 O1 C1 117.3(2) . . ?
C9 O2 C10 117.4(3) . . ?
C18 O3 C17 115.8(3) . . ?
C26 O4 C25 116.6(3) . . ?
O1 C1 H16 109.5 . . ?
O1 C1 H3 109.5 . . ?
H16 C1 H3 109.5 . . ?
O1 C1 H1 109.5 . . ?
H16 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
O1 C2 C3 125.2(3) . . ?
O1 C2 C9 114.2(3) . . ?
C3 C2 C9 120.6(3) . . ?
C2 C3 C4 118.6(3) . . ?
C2 C3 H7 120.7 . . ?
C4 C3 H7 120.7 . . ?
C12 C4 C3 120.5(3) . . ?
C12 C4 C5 111.0(3) . . ?
C3 C4 C5 128.5(3) . . ?
C6 C5 C4 101.9(3) . . ?
C6 C5 C16 112.7(3) . . ?
C4 C5 C16 113.5(3) . . ?
C6 C5 H8 109.5 . . ?
C4 C5 H8 109.5 . . ?
C16 C5 H8 109.5 . . ?
C7 C6 C13 121.0(3) . . ?
C7 C6 C5 129.3(3) . . ?
C13 C6 C5 109.8(3) . . ?
C6 C7 C8 119.2(3) . . ?
C6 C7 H12 120.4 . . ?
C8 C7 H12 120.4 . . ?
C15 C8 C7 120.2(3) . . ?
C15 C8 H2 119.9 . . ?
C7 C8 H2 119.9 . . ?
O2 C9 C11 124.1(3) . . ?
O2 C9 C2 115.2(3) . . ?
C11 C9 C2 120.7(3) . . ?
O2 C10 H5 109.5 . . ?
O2 C10 H4 109.5 . . ?
H5 C10 H4 109.5 . . ?
O2 C10 H6 109.5 . . ?
H5 C10 H6 109.5 . . ?
H4 C10 H6 109.5 . . ?
C9 C11 C12 118.2(3) . . ?
C9 C11 H15 120.9 . . ?
C12 C11 H15 120.9 . . ?
C4 C12 C11 121.3(3) . . ?
C4 C12 C13 108.8(3) . . ?
C11 C12 C13 129.8(3) . . ?
C14 C13 C6 119.4(3) . . ?
C14 C13 C12 132.1(3) . . ?
C6 C13 C12 108.5(3) . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C8 121.1(3) . . ?
C14 C15 H13 119.5 . . ?
C8 C15 H13 119.5 . . ?
C5 C16 H11 109.5 . . ?
C5 C16 H10 109.5 . . ?
H11 C16 H10 109.5 . . ?
C5 C16 H9 109.5 . . ?
H11 C16 H9 109.5 . . ?
H10 C16 H9 109.5 . . ?
O3 C17 H20 109.5 . . ?
O3 C17 H17 109.5 . . ?
H20 C17 H17 109.5 . . ?
O3 C17 H21 109.5 . . ?
H20 C17 H21 109.5 . . ?
H17 C17 H21 109.5 . . ?
O3 C18 C19 125.3(3) . . ?
O3 C18 C26 114.2(3) . . ?
C19 C18 C26 120.5(3) . . ?
C18 C19 C20 119.1(3) . . ?
C18 C19 H22 120.5 . . ?
C20 C19 H22 120.5 . . ?
C27 C20 C19 119.9(3) . . ?
C27 C20 C21 109.3(3) . . ?
C19 C20 C21 130.8(3) . . ?
C22 C21 C29 120.5(3) . . ?
C22 C21 C20 131.6(3) . . ?
C29 C21 C20 107.9(3) . . ?
C23 C22 C21 118.8(3) . . ?
C23 C22 H23 120.6 . . ?
C21 C22 H23 120.6 . . ?
C22 C23 C24 120.8(3) . . ?
C22 C23 H25 119.6 . . ?
C24 C23 H25 119.6 . . ?
C30 C24 C23 120.2(4) . . ?
C30 C24 H18 119.9 . . ?
C23 C24 H18 119.9 . . ?
O4 C25 H19 109.5 . . ?
O4 C25 H31 109.5 . . ?
H19 C25 H31 109.5 . . ?
O4 C25 H32 109.5 . . ?
H19 C25 H32 109.5 . . ?
H31 C25 H32 109.5 . . ?
O4 C26 C32 124.7(3) . . ?
O4 C26 C18 115.3(3) . . ?
C32 C26 C18 120.0(3) . . ?
C32 C27 C20 121.2(3) . . ?
C32 C27 C28 128.1(3) . . ?
C20 C27 C28 110.7(3) . . ?
C27 C28 C31 113.0(3) . . ?
C27 C28 C29 101.4(3) . . ?
C31 C28 C29 112.7(3) . . ?
C27 C28 H26 109.8 . . ?
C31 C28 H26 109.8 . . ?
C29 C28 H26 109.8 . . ?
C30 C29 C21 120.1(3) . . ?
C30 C29 C28 129.3(3) . . ?
C21 C29 C28 110.6(3) . . ?
C29 C30 C24 119.6(3) . . ?
C29 C30 H24 120.2 . . ?
C24 C30 H24 120.2 . . ?
C28 C31 H28 109.5 . . ?
C28 C31 H27 109.5 . . ?
H28 C31 H27 109.5 . . ?
C28 C31 H29 109.5 . . ?
H28 C31 H29 109.5 . . ?
H27 C31 H29 109.5 . . ?
C26 C32 C27 119.3(3) . . ?
C26 C32 H30 120.4 . . ?
C27 C32 H30 120.4 . . ?
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
O1 C2 1.375(4) . ?
O1 C1 1.423(4) . ?
O2 C9 1.373(4) . ?
O2 C10 1.420(4) . ?
O3 C18 1.374(4) . ?
O3 C17 1.429(4) . ?
O4 C26 1.364(4) . ?
O4 C25 1.431(4) . ?
C1 H16 0.9800 . ?
C1 H3 0.9800 . ?
C1 H1 0.9800 . ?
C2 C3 1.389(5) . ?
C2 C9 1.408(5) . ?
C3 C4 1.398(5) . ?
C3 H7 0.9500 . ?
C4 C12 1.387(5) . ?
C4 C5 1.516(4) . ?
C5 C6 1.517(5) . ?
C5 C16 1.534(4) . ?
C5 H8 1.0000 . ?
C6 C7 1.372(5) . ?
C6 C13 1.418(5) . ?
C7 C8 1.396(5) . ?
C7 H12 0.9500 . ?
C8 C15 1.392(5) . ?
C8 H2 0.9500 . ?
C9 C11 1.386(5) . ?
C10 H5 0.9800 . ?
C10 H4 0.9800 . ?
C10 H6 0.9800 . ?
C11 C12 1.399(4) . ?
C11 H15 0.9500 . ?
C12 C13 1.458(5) . ?
C13 C14 1.399(5) . ?
C14 C15 1.383(5) . ?
C14 H14 0.9500 . ?
C15 H13 0.9500 . ?
C16 H11 0.9800 . ?
C16 H10 0.9800 . ?
C16 H9 0.9800 . ?
C17 H20 0.9800 . ?
C17 H17 0.9800 . ?
C17 H21 0.9800 . ?
C18 C19 1.377(5) . ?
C18 C26 1.417(4) . ?
C19 C20 1.402(5) . ?
C19 H22 0.9500 . ?
C20 C27 1.393(4) . ?
C20 C21 1.457(5) . ?
C21 C22 1.392(5) . ?
C21 C29 1.408(5) . ?
C22 C23 1.387(5) . ?
C22 H23 0.9500 . ?
C23 C24 1.395(5) . ?
C23 H25 0.9500 . ?
C24 C30 1.393(5) . ?
C24 H18 0.9500 . ?
C25 H19 0.9800 . ?
C25 H31 0.9800 . ?
C25 H32 0.9800 . ?
C26 C32 1.379(5) . ?
C27 C32 1.383(5) . ?
C27 C28 1.515(5) . ?
C28 C31 1.524(5) . ?
C28 C29 1.523(5) . ?
C28 H26 1.0000 . ?
C29 C30 1.377(5) . ?
C30 H24 0.9500 . ?
C31 H28 0.9800 . ?
C31 H27 0.9800 . ?
C31 H29 0.9800 . ?
C32 H30 0.9500 . ?
