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#$Date: 2019-11-23 21:31:54 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235108 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/67/4036707.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_4036707
loop_
_publ_author_name
'Marshall, Jonathan L.'
'O'Neal, Nathaniel J'
'Zakharov, Lev N.'
'Haley, Michael M.'
_publ_section_title
;
 Synthesis and Characterization of Two Unsymmetrical Indenofluorene
 Analogues: Benzo[5,6]-s-indaceno[1,2-b]thiophene and
 Benzo[5,6]-s-indaceno[2,1-b]thiophene.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3674
_journal_page_last               3680
_journal_paper_doi               10.1021/acs.joc.6b00340
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C36 H30 S'
_chemical_formula_weight         494.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 109.229(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.422(3)
_cell_length_b                   7.1233(15)
_cell_length_c                   13.738(3)
_cell_measurement_reflns_used    2078
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      21.61
_cell_measurement_theta_min      2.99
_cell_volume                     1332.6(5)
_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-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 1.000
_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  0.0734
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16075
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.992
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       plate
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0496
_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)+(0.0461P)²+0.8694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1202
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1625
_reflns_number_total             2360
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b00340_si_003.cif
_cod_data_source_block           mh143
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036707
_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   0.977
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S1A S 0.4358(3) 0.3533(6) 0.6723(2) 0.0278(7) Uani 0.5 1 d . . P A 1
C4A C 0.42234(16) 0.4466(3) 0.78386(18) 0.0231(5) Uani 0.5 1 d . . P A 1
C8A C 0.3124(3) 0.4593(4) 0.5913(2) 0.0451(8) Uani 0.5 1 d . . P A 1
C4 C 0.42234(16) 0.4466(3) 0.78386(18) 0.0231(5) Uani 0.5 1 d . . P A 2
C8 C 0.3124(3) 0.4593(4) 0.5913(2) 0.0451(8) Uani 0.5 1 d . . P A 2
C9 C 0.3855(5) 0.3729(8) 0.6081(6) 0.0281(13) Uani 0.5 1 d . . P A 2
C10 C 0.4497(13) 0.356(2) 0.7124(8) 0.030(3) Uani 0.5 1 d . . P A 2
C1 C 0.44071(16) 0.6141(3) 1.04364(19) 0.0238(6) Uani 1 1 d . . . . .
C2 C 0.41036(16) 0.5727(3) 0.93609(18) 0.0229(5) Uani 1 1 d . . . . .
C3 C 0.47254(16) 0.4576(3) 0.89456(18) 0.0224(5) Uani 1 1 d . . . . .
C5 C 0.33471(16) 0.5482(3) 0.76048(18) 0.0230(5) Uani 1 1 d . . . . .
C6 C 0.32704(16) 0.6261(3) 0.85646(18) 0.0231(5) Uani 1 1 d . . . . .
C7 C 0.27609(18) 0.5541(4) 0.6567(2) 0.0313(6) Uani 1 1 d . . . . .
C11 C 0.24033(16) 0.7320(3) 0.86176(17) 0.0228(5) Uani 1 1 d . . . . .
C12 C 0.21820(17) 0.9088(3) 0.81449(19) 0.0277(6) Uani 1 1 d . . . . .
C13 C 0.13154(18) 0.9981(4) 0.8125(2) 0.0332(6) Uani 1 1 d . . . . .
C14 C 0.06827(17) 0.9201(4) 0.85851(19) 0.0341(7) Uani 1 1 d . . . . .
C15 C 0.09252(18) 0.7475(4) 0.90627(19) 0.0319(6) Uani 1 1 d . . . . .
C16 C 0.17713(16) 0.6510(3) 0.90896(18) 0.0259(6) Uani 1 1 d . . . . .
C17 C 0.2880(2) 1.0065(4) 0.7700(2) 0.0416(7) Uani 1 1 d . . . . .
H17A H 0.2599 1.1272 0.7404 0.062 Uiso 1 1 calc R U . . .
H17B H 0.2985 0.9279 0.7160 0.062 Uiso 1 1 calc R U . . .
H17C H 0.3509 1.0277 0.8246 0.062 Uiso 1 1 calc R U . . .
C18 C -0.0251(2) 1.0188(5) 0.8548(2) 0.0536(9) Uani 1 1 d . . . . .
H18A H -0.0603 0.9433 0.8911 0.080 Uiso 1 1 calc R U . . .
H18B H -0.0667 1.0356 0.7829 0.080 Uiso 1 1 calc R U . . .
H18C H -0.0093 1.1418 0.8882 0.080 Uiso 1 1 calc R U . . .
C19 C 0.19704(18) 0.4599(4) 0.9586(2) 0.0375(7) Uani 1 1 d . . . . .
H19A H 0.1450 0.4279 0.9870 0.056 Uiso 1 1 calc R U . . .
H19B H 0.2605 0.4612 1.0142 0.056 Uiso 1 1 calc R U . . .
H19C H 0.1985 0.3662 0.9069 0.056 Uiso 1 1 calc R U . . .
H1 H 0.4007(15) 0.687(3) 1.0720(16) 0.018(6) Uiso 1 1 d . . . . .
H7 H 0.213(2) 0.618(4) 0.630(2) 0.056(9) Uiso 1 1 d . . . . .
H8 H 0.280(3) 0.462(5) 0.521(3) 0.092(13) Uiso 1 1 d . . . . .
H9 H 0.404(4) 0.329(7) 0.544(4) 0.043(15) Uiso 0.5 1 d . . P . .
H10 H 0.520(4) 0.283(7) 0.727(4) 0.033(13) Uiso 0.5 1 d . . P . .
H13 H 0.1195(18) 1.123(4) 0.780(2) 0.042(8) Uiso 1 1 d . . . . .
H15 H 0.0492(17) 0.682(3) 0.9405(18) 0.029(6) Uiso 1 1 d . . . . .
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'
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
C4A S1A C8A 90.5(2) .
C5 C4A C3 108.3(2) .
C5 C4A S1A 110.5(2) .
C3 C4A S1A 141.2(2) .
C7 C8A S1A 107.4(2) .
C3 C1 C2 118.4(2) 3_667
C6 C2 C1 130.7(2) .
C6 C2 C3 109.3(2) .
C1 C2 C3 120.1(2) .
C1 C3 C4A 132.2(2) 3_667
C1 C3 C2 121.6(2) 3_667
C4A C3 C2 106.24(18) .
C4A C5 C7 116.5(2) .
C4A C5 C6 108.6(2) .
C7 C5 C6 134.9(2) .
C2 C6 C5 107.65(19) .
C2 C6 C11 128.8(2) .
C5 C6 C11 123.4(2) .
C8A C7 C5 115.1(3) .
C16 C11 C12 119.9(2) .
C16 C11 C6 120.0(2) .
C12 C11 C6 120.0(2) .
C13 C12 C11 118.9(2) .
C13 C12 C17 119.6(2) .
C11 C12 C17 121.4(2) .
C14 C13 C12 121.9(3) .
C15 C14 C13 118.1(2) .
C15 C14 C18 121.0(3) .
C13 C14 C18 120.9(3) .
C14 C15 C16 122.3(2) .
C15 C16 C11 118.8(2) .
C15 C16 C19 119.6(2) .
C11 C16 C19 121.6(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1A C4A 1.740(4) .
S1A C8A 1.916(6) .
C4A C5 1.399(3) .
C4A C3 1.455(3) .
C8A C7 1.359(4) .
C9 C10 1.432(10) .
C1 C3 1.359(3) 3_667
C1 C2 1.427(3) .
C2 C6 1.385(3) .
C2 C3 1.463(3) .
C3 C1 1.359(3) 3_667
C5 C7 1.398(3) .
C5 C6 1.468(3) .
C6 C11 1.483(3) .
C11 C16 1.405(3) .
C11 C12 1.404(3) .
C12 C13 1.395(3) .
C12 C17 1.509(3) .
C13 C14 1.386(4) .
C14 C15 1.384(4) .
C14 C18 1.506(3) .
C15 C16 1.390(3) .
C16 C19 1.507(4) .
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_4
C8A S1A C4A C5 -0.8(3) . .
C8A S1A C4A C3 -179.5(3) . .
C3 C1 C2 C6 -179.9(2) 3_667 .
C3 C1 C2 C3 -0.6(4) 3_667 .
C5 C4A C3 C1 -179.5(2) . 3_667
S1A C4A C3 C1 -0.8(5) . 3_667
C5 C4A C3 C2 -0.4(2) . .
S1A C4A C3 C2 178.3(3) . .
C6 C2 C3 C1 -179.9(2) . 3_667
C1 C2 C3 C1 0.7(4) . 3_667
C6 C2 C3 C4A 0.9(2) . .
C1 C2 C3 C4A -178.5(2) . .
C3 C4A C5 C7 179.9(2) . .
S1A C4A C5 C7 0.7(3) . .
C3 C4A C5 C6 -0.2(3) . .
S1A C4A C5 C6 -179.3(2) . .
C1 C2 C6 C5 178.3(2) . .
C3 C2 C6 C5 -1.0(3) . .
C1 C2 C6 C11 -5.2(4) . .
C3 C2 C6 C11 175.5(2) . .
C4A C5 C6 C2 0.7(3) . .
C7 C5 C6 C2 -179.3(3) . .
C4A C5 C6 C11 -176.0(2) . .
C7 C5 C6 C11 4.0(4) . .
S1A C8A C7 C5 -0.5(3) . .
C4A C5 C7 C8A -0.1(3) . .
C6 C5 C7 C8A 180.0(3) . .
C2 C6 C11 C16 -66.9(3) . .
C5 C6 C11 C16 109.1(3) . .
C2 C6 C11 C12 116.7(3) . .
C5 C6 C11 C12 -67.3(3) . .
C16 C11 C12 C13 -2.1(3) . .
C6 C11 C12 C13 174.3(2) . .
C16 C11 C12 C17 175.4(2) . .
C6 C11 C12 C17 -8.2(4) . .
C11 C12 C13 C14 2.0(4) . .
C17 C12 C13 C14 -175.6(2) . .
C12 C13 C14 C15 -0.8(4) . .
C12 C13 C14 C18 -179.7(3) . .
C13 C14 C15 C16 -0.3(4) . .
C18 C14 C15 C16 178.6(2) . .
C14 C15 C16 C11 0.2(4) . .
C14 C15 C16 C19 -177.6(2) . .
C12 C11 C16 C15 1.0(3) . .
C6 C11 C16 C15 -175.4(2) . .
C12 C11 C16 C19 178.7(2) . .
C6 C11 C16 C19 2.3(3) . .
