#------------------------------------------------------------------------------
#$Date: 2020-08-07 02:27:20 +0300 (Fri, 07 Aug 2020) $
#$Revision: 255144 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/86/4038656.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_4038656
loop_
_publ_author_name
'Dressler, Justin'
'Barker, Joshua E.'
'Karas, Lucas J.'
'Hashimoto, Hannah'
'Kishi, Ryohei'
'Zakharov, Lev N.'
'MacMillan, Samantha N.'
'Gómez-García, Carlos J'
'Nakano, Masayoshi'
'Wu, Judy I.'
'Haley, Michael M.'
_publ_section_title
;
 Late-stage Modification of Electronic Properties of Antiaromatic and
 Diradicaloid Indeno[1,2-b]fluorene Analogues via Sulfur Oxidation.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01387
_journal_year                    2020
_chemical_formula_sum            'C43 H33 Cl3 O4 S2'
_chemical_formula_weight         784.16
_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-2017/1
_cell_angle_alpha                75.860(2)
_cell_angle_beta                 73.582(2)
_cell_angle_gamma                84.176(2)
_cell_formula_units_Z            1
_cell_length_a                   8.1459(3)
_cell_length_b                   9.0608(4)
_cell_length_c                   13.5621(5)
_cell_measurement_reflns_used    5252
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.53
_cell_measurement_theta_min      5.04
_cell_volume                     930.52(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8785
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        66.525
_diffrn_reflns_theta_max         66.525
_diffrn_reflns_theta_min         3.487
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    3.628
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       prizm
_exptl_crystal_F_000             406
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0530
_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)+(0.0563P)²+1.4494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1411
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3005
_reflns_number_total             3229
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01387_si_002.cif
_cod_data_source_block           cu_mh236_0m_a
_cod_database_code               4038656
_shelx_shelxl_version_number     2017/1
_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_min   0.736
_shelx_estimated_absorpt_t_max   0.899
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 0.59212(8) 0.46334(7) 0.67777(5) 0.0212(2) Uani 1 1 d . . . . .
O1 O 0.4256(2) 0.5035(3) 0.66114(15) 0.0328(5) Uani 1 1 d . . . . .
O2 O 0.6518(3) 0.3078(2) 0.68425(16) 0.0327(5) Uani 1 1 d . . . . .
C1 C 0.4178(3) 0.3948(3) 0.9646(2) 0.0200(5) Uani 1 1 d . . . . .
H1B H 0.364836 0.327280 0.940321 0.024 Uiso 1 1 calc R U . . .
C2 C 0.5414(3) 0.4982(3) 0.89392(19) 0.0193(5) Uani 1 1 d . . . . .
C3 C 0.6217(3) 0.6032(3) 0.9306(2) 0.0200(5) Uani 1 1 d . . . . .
C4 C 0.7420(3) 0.6941(3) 0.83965(19) 0.0196(5) Uani 1 1 d . . . . .
C5 C 0.7361(3) 0.6439(3) 0.7529(2) 0.0210(5) Uani 1 1 d . . . . .
C6 C 0.6130(3) 0.5266(3) 0.7859(2) 0.0204(5) Uani 1 1 d . . . . .
C7 C 0.8151(3) 0.6773(3) 0.63902(19) 0.0197(5) Uani 1 1 d . . . . .
C8 C 0.7487(3) 0.5901(3) 0.5876(2) 0.0207(5) Uani 1 1 d . . . . .
C9 C 0.8016(3) 0.6020(3) 0.4800(2) 0.0256(6) Uani 1 1 d . . . . .
H9A H 0.753075 0.542520 0.447288 0.031 Uiso 1 1 calc R U . . .
C10 C 0.9279(4) 0.7039(3) 0.4216(2) 0.0300(6) Uani 1 1 d . . . . .
H10A H 0.967332 0.714968 0.347332 0.036 Uiso 1 1 calc R U . . .
C11 C 0.9981(4) 0.7905(3) 0.4705(2) 0.0286(6) Uani 1 1 d . . . . .
H11A H 1.085752 0.858904 0.428943 0.034 Uiso 1 1 calc R U . . .
C12 C 0.9426(3) 0.7790(3) 0.5785(2) 0.0253(6) Uani 1 1 d . . . . .
H12A H 0.990696 0.839420 0.610794 0.030 Uiso 1 1 calc R U . . .
C13 C 0.8391(3) 0.8200(3) 0.84551(18) 0.0189(5) Uani 1 1 d . . . . .
C14 C 0.7542(3) 0.9602(3) 0.8561(2) 0.0215(5) Uani 1 1 d . . . . .
C15 C 0.8461(4) 1.0776(3) 0.8622(2) 0.0252(6) Uani 1 1 d . . . . .
H15A H 0.788739 1.172689 0.869162 0.030 Uiso 1 1 calc R U . . .
C16 C 1.0184(4) 1.0600(3) 0.8584(2) 0.0274(6) Uani 1 1 d . . . . .
C17 C 1.0995(3) 0.9198(3) 0.8490(2) 0.0303(6) Uani 1 1 d . . . . .
H17A H 1.217272 0.905633 0.847360 0.036 Uiso 1 1 calc R U . . .
C18 C 1.0133(3) 0.7996(3) 0.8419(2) 0.0255(6) Uani 1 1 d . . . . .
C19 C 0.5671(4) 0.9855(3) 0.8588(3) 0.0335(7) Uani 1 1 d . . . . .
H19A H 0.5494(8) 0.961(3) 0.8006(16) 0.050 Uiso 1 1 calc R U . . .
H19B H 0.5354(11) 1.086(2) 0.8583(19) 0.050 Uiso 1 1 calc R U . . .
H19C H 0.5023(15) 0.925(2) 0.9192(16) 0.050 Uiso 1 1 calc R U . . .
C20 C 1.1164(4) 1.1885(4) 0.8656(3) 0.0393(8) Uani 1 1 d . . . . .
H20A H 1.235779 1.154580 0.861535 0.059 Uiso 1 1 calc R U . . .
H20B H 1.112452 1.276010 0.807189 0.059 Uiso 1 1 calc R U . . .
H20C H 1.064382 1.218046 0.932858 0.059 Uiso 1 1 calc R U . . .
C21 C 1.1057(4) 0.6486(4) 0.8323(3) 0.0459(9) Uani 1 1 d . . . . .
H21A H 1.026266 0.577477 0.828185 0.069 Uiso 1 1 calc R U . . .
H21B H 1.201512 0.663155 0.768391 0.069 Uiso 1 1 calc R U . . .
H21C H 1.149468 0.607071 0.894217 0.069 Uiso 1 1 calc R U . . .
Cl1S Cl 0.6117(3) 0.0440(3) 0.37724(15) 0.0719(6) Uani 0.5 1 d . . P A -1
Cl2S Cl 0.3987(3) -0.1537(2) 0.5600(2) 0.0632(6) Uani 0.5 1 d . . P A -1
Cl3S Cl 0.5300(3) 0.1183(2) 0.57846(15) 0.0551(5) Uani 0.5 1 d . . P A -1
C1S C 0.4541(9) 0.0348(7) 0.4980(5) 0.0377(15) Uani 0.5 1 d . . P A -1
H1SA H 0.349571 0.093953 0.483586 0.045 Uiso 0.5 1 calc R U P A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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 O1 117.82(13) . . ?
O2 S1 C6 110.45(12) . . ?
O1 S1 C6 110.96(12) . . ?
O2 S1 C8 111.19(12) . . ?
O1 S1 C8 111.40(12) . . ?
C6 S1 C8 92.10(12) . . ?
C3 C1 C2 117.1(2) 2_667 . ?
C3 C1 H1B 121.4 2_667 . ?
C2 C1 H1B 121.4 . . ?
C6 C2 C1 133.2(2) . . ?
C6 C2 C3 105.1(2) . . ?
C1 C2 C3 121.7(2) . . ?
C1 C3 C2 121.2(2) 2_667 . ?
C1 C3 C4 130.1(2) 2_667 . ?
C2 C3 C4 108.7(2) . . ?
C5 C4 C3 106.5(2) . . ?
C5 C4 C13 129.4(2) . . ?
C3 C4 C13 124.0(2) . . ?
C4 C5 C6 108.9(2) . . ?
C4 C5 C7 138.6(2) . . ?
C6 C5 C7 112.5(2) . . ?
C2 C6 C5 110.8(2) . . ?
C2 C6 S1 138.0(2) . . ?
C5 C6 S1 111.22(19) . . ?
C12 C7 C8 118.3(2) . . ?
C12 C7 C5 129.4(2) . . ?
C8 C7 C5 112.2(2) . . ?
C9 C8 C7 123.2(2) . . ?
C9 C8 S1 124.9(2) . . ?
C7 C8 S1 111.93(19) . . ?
C8 C9 C10 117.4(3) . . ?
C8 C9 H9A 121.3 . . ?
C10 C9 H9A 121.3 . . ?
C9 C10 C11 120.8(2) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C12 C11 C10 121.3(3) . . ?
C12 C11 H11A 119.3 . . ?
C10 C11 H11A 119.3 . . ?
C11 C12 C7 119.0(3) . . ?
C11 C12 H12A 120.5 . . ?
C7 C12 H12A 120.5 . . ?
C18 C13 C14 119.9(2) . . ?
C18 C13 C4 120.7(2) . . ?
C14 C13 C4 119.3(2) . . ?
C15 C14 C13 119.0(2) . . ?
C15 C14 C19 120.1(2) . . ?
C13 C14 C19 120.9(2) . . ?
C16 C15 C14 122.0(3) . . ?
C16 C15 H15A 119.0 . . ?
C14 C15 H15A 119.0 . . ?
C15 C16 C17 118.1(2) . . ?
C15 C16 C20 121.4(3) . . ?
C17 C16 C20 120.5(3) . . ?
C16 C17 C18 122.0(3) . . ?
C16 C17 H17A 119.0 . . ?
C18 C17 H17A 119.0 . . ?
C17 C18 C13 119.0(3) . . ?
C17 C18 C21 120.4(3) . . ?
C13 C18 C21 120.6(3) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Cl3S C1S Cl2S 110.9(4) . . ?
Cl3S C1S Cl1S 109.0(4) . . ?
Cl2S C1S Cl1S 111.1(4) . . ?
Cl3S C1S H1SA 108.6 . . ?
Cl2S C1S H1SA 108.6 . . ?
Cl1S C1S H1SA 108.6 . . ?
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 1.434(2) . ?
S1 O1 1.434(2) . ?
S1 C6 1.754(3) . ?
S1 C8 1.781(3) . ?
C1 C3 1.370(4) 2_667 ?
C1 C2 1.420(3) . ?
C1 H1B 0.9500 . ?
C2 C6 1.384(4) . ?
C2 C3 1.457(3) . ?
C3 C4 1.464(3) . ?
C4 C5 1.375(4) . ?
C4 C13 1.482(3) . ?
C5 C6 1.438(4) . ?
C5 C7 1.463(3) . ?
C7 C12 1.394(4) . ?
C7 C8 1.404(4) . ?
C8 C9 1.380(4) . ?
C9 C10 1.384(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.393(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.386(4) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C18 1.401(4) . ?
C13 C14 1.403(4) . ?
C14 C15 1.391(4) . ?
C14 C19 1.510(4) . ?
C15 C16 1.385(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.388(4) . ?
C16 C20 1.513(4) . ?
C17 C18 1.390(4) . ?
C17 H17A 0.9500 . ?
C18 C21 1.510(4) . ?
C19 H19A 0.920(19) . ?
C19 H19B 0.920(19) . ?
C19 H19C 0.92(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
Cl1S C1S 1.762(7) . ?
Cl2S C1S 1.752(7) . ?
Cl3S C1S 1.740(7) . ?
C1S H1SA 1.0000 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9A O1 0.95 2.47 3.355(3) 155.6 2_666 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 C6 179.1(3) 2_667 . . . ?
C3 C1 C2 C3 -0.7(4) 2_667 . . . ?
C6 C2 C3 C1 -179.1(2) . . . 2_667 ?
C1 C2 C3 C1 0.7(4) . . . 2_667 ?
C6 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C4 -179.9(2) . . . . ?
C1 C3 C4 C5 178.3(3) 2_667 . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C1 C3 C4 C13 -4.8(4) 2_667 . . . ?
C2 C3 C4 C13 175.8(2) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C13 C4 C5 C6 -175.3(3) . . . . ?
C3 C4 C5 C7 179.7(3) . . . . ?
C13 C4 C5 C7 3.1(5) . . . . ?
C1 C2 C6 C5 -179.3(3) . . . . ?
C3 C2 C6 C5 0.5(3) . . . . ?
C1 C2 C6 S1 2.8(5) . . . . ?
C3 C2 C6 S1 -177.4(2) . . . . ?
C4 C5 C6 C2 -1.2(3) . . . . ?
C7 C5 C6 C2 179.9(2) . . . . ?
C4 C5 C6 S1 177.33(18) . . . . ?
C7 C5 C6 S1 -1.5(3) . . . . ?
O2 S1 C6 C2 -67.8(3) . . . . ?
O1 S1 C6 C2 64.8(3) . . . . ?
C8 S1 C6 C2 178.7(3) . . . . ?
O2 S1 C6 C5 114.3(2) . . . . ?
O1 S1 C6 C5 -113.2(2) . . . . ?
C8 S1 C6 C5 0.7(2) . . . . ?
C4 C5 C7 C12 3.9(5) . . . . ?
C6 C5 C7 C12 -177.7(3) . . . . ?
C4 C5 C7 C8 -176.6(3) . . . . ?
C6 C5 C7 C8 1.8(3) . . . . ?
C12 C7 C8 C9 -1.0(4) . . . . ?
C5 C7 C8 C9 179.4(2) . . . . ?
C12 C7 C8 S1 178.35(19) . . . . ?
C5 C7 C8 S1 -1.2(3) . . . . ?
O2 S1 C8 C9 66.8(3) . . . . ?
O1 S1 C8 C9 -66.8(3) . . . . ?
C6 S1 C8 C9 179.7(2) . . . . ?
O2 S1 C8 C7 -112.6(2) . . . . ?
O1 S1 C8 C7 113.8(2) . . . . ?
C6 S1 C8 C7 0.3(2) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
S1 C8 C9 C10 -178.4(2) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C10 C11 C12 C7 0.6(4) . . . . ?
C8 C7 C12 C11 0.2(4) . . . . ?
C5 C7 C12 C11 179.7(3) . . . . ?
C5 C4 C13 C18 -80.0(4) . . . . ?
C3 C4 C13 C18 103.9(3) . . . . ?
C5 C4 C13 C14 100.8(3) . . . . ?
C3 C4 C13 C14 -75.3(3) . . . . ?
C18 C13 C14 C15 0.4(4) . . . . ?
C4 C13 C14 C15 179.6(2) . . . . ?
C18 C13 C14 C19 179.2(2) . . . . ?
C4 C13 C14 C19 -1.6(4) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C19 C14 C15 C16 -179.0(2) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C14 C15 C16 C20 -179.7(3) . . . . ?
C15 C16 C17 C18 0.9(4) . . . . ?
C20 C16 C17 C18 -179.8(3) . . . . ?
C16 C17 C18 C13 -0.8(4) . . . . ?
C16 C17 C18 C21 -179.6(3) . . . . ?
C14 C13 C18 C17 0.1(4) . . . . ?
C4 C13 C18 C17 -179.2(2) . . . . ?
C14 C13 C18 C21 178.9(3) . . . . ?
C4 C13 C18 C21 -0.3(4) . . . . ?
