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#$Date: 2019-11-11 20:49:16 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227318 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/59/4035925.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_4035925
loop_
_publ_author_name
'Kolanji, Kubandiran'
'Postulka, Lars'
'Wolf, Bernd'
'Lang, Michael'
'Schollmeyer, Dieter'
'Baumgarten, Martin'
_publ_section_title
;
 Planar Benzo[1,2- b:4,5- b']dithiophene Derivatives Decorated with
 Nitronyl and Imino Nitroxides.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              140
_journal_page_last               149
_journal_paper_doi               10.1021/acs.joc.8b02499
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C34 H36 N4 O6 S4'
_chemical_formula_sum            'C34 H36 N4 O6 S4'
_chemical_formula_weight         724.91
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.457(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.173(8)
_cell_length_b                   6.265(3)
_cell_length_c                   16.682(8)
_cell_measurement_reflns_used    1253
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      2.5
_cell_volume                     1650.5(14)
_computing_cell_refinement       'APEX II Suite'
_computing_data_collection       'APEX II Suite'
_computing_data_reduction        'APEX II Suite'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Smart APEX II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1594
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3864
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.959
_diffrn_reflns_theta_min         2.501
_exptl_absorpt_coefficient_mu    0.341
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3864
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1522
_refine_ls_R_factor_gt           0.0768
_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)+(0.0700P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1724
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2197
_reflns_number_total             3864
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b02499_si_002.cif
_cod_data_source_block           bdtth2-nn
_cod_original_cell_volume        1650.6(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035925
_shelx_shelxl_version_number     2014/7
_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   0.832
_shelx_estimated_absorpt_t_max   0.986
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
C1 C 0.4978(4) 0.4834(9) 0.5848(3) 0.0243(13) Uani 1 1 d . . . . .
C2 C 0.4547(4) 0.6438(9) 0.5357(4) 0.0260(13) Uani 1 1 d D . . . .
C3 C 0.4019(5) 0.8146(10) 0.5534(5) 0.0253(15) Uani 0.906(5) 1 d D . P A 1
H3 H 0.3899 0.8295 0.6064 0.030 Uiso 0.906(5) 1 calc R U P A 1
C4 C 0.3702(4) 0.9520(9) 0.4930(3) 0.0214(13) Uani 1 1 d D . . . .
S5 S 0.40075(12) 0.8757(3) 0.40184(11) 0.0240(5) Uani 0.906(5) 1 d D . P A 1
C6 C 0.4568(4) 0.6616(8) 0.4515(4) 0.0231(14) Uani 1 1 d D . . . .
S3 S 0.3971(13) 0.807(3) 0.5858(9) 0.0240(5) Uani 0.094(5) 1 d D . P A 2
C5 C 0.399(4) 0.845(8) 0.4338(16) 0.0253(15) Uani 0.094(5) 1 d D . P A 2
H5 H 0.3812 0.8914 0.3785 0.030 Uiso 0.094(5) 1 calc R U P A 2
O7 O 0.4932(3) 0.4690(7) 0.6655(3) 0.0379(11) Uani 1 1 d . . . . .
C8 C 0.5528(5) 0.5909(12) 0.7192(4) 0.054(2) Uani 1 1 d . . . . .
H8A H 0.6094 0.5311 0.7223 0.082 Uiso 1 1 calc R U . . .
H8B H 0.5396 0.5890 0.7739 0.082 Uiso 1 1 calc R U . . .
H8C H 0.5512 0.7382 0.6992 0.082 Uiso 1 1 calc R U . . .
C9 C 0.3167(4) 1.1349(9) 0.4942(4) 0.0242(14) Uani 1 1 d . . . . .
C10 C 0.2770(4) 1.2648(9) 0.4331(3) 0.0278(15) Uani 1 1 d . . . . .
H10 H 0.2806 1.2457 0.3775 0.033 Uiso 1 1 calc R U . . .
C11 C 0.2306(4) 1.4279(9) 0.4583(4) 0.0268(14) Uani 1 1 d . . . . .
H11 H 0.2004 1.5326 0.4223 0.032 Uiso 1 1 calc R U . . .
C12 C 0.2335(4) 1.4211(9) 0.5420(4) 0.0241(14) Uani 1 1 d . . . . .
S13 S 0.29772(10) 1.2150(2) 0.58773(10) 0.0272(4) Uani 1 1 d . . . . .
C14 C 0.1894(4) 1.5527(9) 0.5889(4) 0.0259(14) Uani 1 1 d . . . . .
N15 N 0.1350(3) 1.7141(8) 0.5615(3) 0.0282(11) Uani 1 1 d . . . . .
C16 C 0.0879(4) 1.7815(9) 0.6259(4) 0.0293(14) Uani 1 1 d . . . . .
C17 C 0.1495(4) 1.7017(9) 0.7044(4) 0.0284(14) Uani 1 1 d . . . . .
N18 N 0.1940(3) 1.5280(8) 0.6703(3) 0.0282(12) Uani 1 1 d . . . . .
O19 O 0.1150(3) 1.7807(7) 0.4874(3) 0.0362(11) Uani 1 1 d . . . . .
C20 C 0.0742(4) 2.0228(9) 0.6219(4) 0.0308(14) Uani 1 1 d . . . . .
H20A H 0.1278 2.0944 0.6206 0.046 Uiso 1 1 calc R U . . .
H20B H 0.0540 2.0699 0.6703 0.046 Uiso 1 1 calc R U . . .
H20C H 0.0320 2.0589 0.5722 0.046 Uiso 1 1 calc R U . . .
C21 C 0.0032(4) 1.6656(10) 0.6049(4) 0.0393(17) Uani 1 1 d . . . . .
H21A H -0.0249 1.6972 0.5480 0.059 Uiso 1 1 calc R U . . .
H21B H -0.0326 1.7136 0.6418 0.059 Uiso 1 1 calc R U . . .
H21C H 0.0127 1.5115 0.6113 0.059 Uiso 1 1 calc R U . . .
C22 C 0.2166(4) 1.8662(10) 0.7422(4) 0.0387(17) Uani 1 1 d . . . . .
H22A H 0.2604 1.7969 0.7838 0.058 Uiso 1 1 calc R U . . .
H22B H 0.1901 1.9806 0.7678 0.058 Uiso 1 1 calc R U . . .
H22C H 0.2424 1.9263 0.6991 0.058 Uiso 1 1 calc R U . . .
C23 C 0.1072(4) 1.6114(10) 0.7706(4) 0.0416(18) Uani 1 1 d . . . . .
H23A H 0.0656 1.5030 0.7463 0.062 Uiso 1 1 calc R U . . .
H23B H 0.0786 1.7267 0.7937 0.062 Uiso 1 1 calc R U . . .
H23C H 0.1502 1.5465 0.8143 0.062 Uiso 1 1 calc R U . . .
O24 O 0.2406(3) 1.3876(6) 0.7161(3) 0.0388(12) Uani 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'
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'
N N 0.0061 0.0033 '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
O7 C1 C2 120.2(6) . .
O7 C1 C6 122.2(6) . 3_666
C2 C1 C6 117.6(5) . 3_666
C1 C2 C6 121.8(5) . .
C1 C2 C3 131.5(6) . .
C6 C2 C3 106.7(6) . .
C1 C2 S3 113.6(6) . .
C6 C2 S3 124.6(6) . .
C4 C3 C2 118.1(6) . .
C4 C3 H3 120.9 . .
C2 C3 H3 120.9 . .
C3 C4 C9 129.5(5) . .
C5 C4 C9 134.8(10) . .
C3 C4 S5 110.0(5) . .
C9 C4 S5 120.6(4) . .
C5 C4 S3 109.0(11) . .
C9 C4 S3 115.7(6) . .
C6 S5 C4 90.7(3) . .
C1 C6 C2 120.6(5) 3_666 .
C1 C6 C5 143.0(10) 3_666 .
C2 C6 C5 96.3(9) . .
C1 C6 S5 124.9(5) 3_666 .
C2 C6 S5 114.5(4) . .
C2 S3 C4 86.4(6) . .
C4 C5 C6 122.9(16) . .
C4 C5 H5 118.6 . .
C6 C5 H5 118.6 . .
C1 O7 C8 114.8(6) . .
O7 C8 H8A 109.5 . .
O7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
O7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 C4 131.2(5) . .
C10 C9 S13 110.9(4) . .
C4 C9 S13 117.9(4) . .
C9 C10 C11 114.6(5) . .
C9 C10 H10 122.7 . .
C11 C10 H10 122.7 . .
C10 C11 C12 112.3(5) . .
C10 C11 H11 123.8 . .
C12 C11 H11 123.8 . .
C11 C12 C14 128.4(5) . .
C11 C12 S13 110.7(4) . .
C14 C12 S13 120.9(4) . .
C12 S13 C9 91.5(3) . .
N18 C14 N15 108.3(5) . .
N18 C14 C12 123.9(6) . .
N15 C14 C12 127.7(5) . .
O19 N15 C14 125.5(5) . .
O19 N15 C16 122.5(5) . .
C14 N15 C16 111.2(5) . .
N15 C16 C21 105.7(5) . .
N15 C16 C20 109.7(5) . .
C21 C16 C20 110.3(5) . .
N15 C16 C17 100.4(5) . .
C21 C16 C17 115.1(5) . .
C20 C16 C17 114.6(5) . .
N18 C17 C23 109.6(5) . .
N18 C17 C22 107.0(5) . .
C23 C17 C22 109.9(6) . .
N18 C17 C16 100.9(5) . .
C23 C17 C16 115.1(5) . .
C22 C17 C16 113.6(5) . .
O24 N18 C14 124.6(5) . .
O24 N18 C17 122.7(5) . .
C14 N18 C17 112.0(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 . .
C16 C21 H21A 109.5 . .
C16 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C16 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C17 C22 H22A 109.5 . .
C17 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C17 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C17 C23 H23A 109.5 . .
C17 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C17 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O7 1.366(7) .
C1 C2 1.385(8) .
C1 C6 1.387(8) 3_666
C2 C6 1.417(8) .
C2 C3 1.439(9) .
C2 S3 1.716(14) .
C3 C4 1.341(9) .
C3 H3 0.9500 .
C4 C5 1.355(19) .
C4 C9 1.438(7) .
C4 S5 1.764(5) .
C4 S3 1.767(14) .
S5 C6 1.728(6) .
C6 C1 1.387(8) 3_666
C6 C5 1.473(19) .
C5 H5 0.9500 .
O7 C8 1.394(8) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.353(8) .
C9 S13 1.729(6) .
C10 C11 1.385(8) .
C10 H10 0.9500 .
C11 C12 1.389(8) .
C11 H11 0.9500 .
C12 C14 1.427(8) .
C12 S13 1.728(6) .
C14 N18 1.354(7) .
C14 N15 1.354(7) .
N15 O19 1.279(6) .
N15 C16 1.505(7) .
C16 C21 1.523(9) .
C16 C20 1.527(8) .
C16 C17 1.549(9) .
C17 N18 1.484(7) .
C17 C23 1.528(9) .
C17 C22 1.530(9) .
N18 O24 1.295(6) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
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
O7 C1 C2 C6 -178.9(6) . .
C6 C1 C2 C6 -0.4(10) 3_666 .
O7 C1 C2 C3 0.5(11) . .
C6 C1 C2 C3 179.1(6) 3_666 .
O7 C1 C2 S3 -1.2(11) . .
C6 C1 C2 S3 177.3(9) 3_666 .
C1 C2 C3 C4 178.0(7) . .
C6 C2 C3 C4 -2.5(8) . .
C2 C3 C4 C9 -179.7(6) . .
C2 C3 C4 S5 2.2(8) . .
C3 C4 S5 C6 -0.9(5) . .
C9 C4 S5 C6 -179.2(5) . .
C1 C2 C6 C1 0.4(10) . 3_666
C3 C2 C6 C1 -179.2(6) . 3_666
S3 C2 C6 C1 -177.0(10) . 3_666
C1 C2 C6 C5 178(3) . .
S3 C2 C6 C5 0(3) . .
C1 C2 C6 S5 -178.7(5) . .
C3 C2 C6 S5 1.7(7) . .
C4 S5 C6 C1 -179.6(5) . 3_666
C4 S5 C6 C2 -0.6(5) . .
C1 C2 S3 C4 177.9(6) . .
C6 C2 S3 C4 -4.5(12) . .
C5 C4 S3 C2 7(4) . .
C9 C4 S3 C2 -179.2(6) . .
C9 C4 C5 C6 178(3) . .
S3 C4 C5 C6 -10(7) . .
C1 C6 C5 C4 -177(2) 3_666 .
C2 C6 C5 C4 7(6) . .
C2 C1 O7 C8 -87.2(8) . .
C6 C1 O7 C8 94.3(7) 3_666 .
C3 C4 C9 C10 -172.8(7) . .
C5 C4 C9 C10 -1(5) . .
S5 C4 C9 C10 5.2(9) . .
S3 C4 C9 C10 -171.7(9) . .
C3 C4 C9 S13 8.1(9) . .
C5 C4 C9 S13 -180(5) . .
S5 C4 C9 S13 -173.9(3) . .
S3 C4 C9 S13 9.3(10) . .
C4 C9 C10 C11 -179.6(6) . .
S13 C9 C10 C11 -0.5(7) . .
C9 C10 C11 C12 -1.2(8) . .
C10 C11 C12 C14 -175.5(6) . .
C10 C11 C12 S13 2.2(7) . .
C11 C12 S13 C9 -2.1(5) . .
C14 C12 S13 C9 175.8(5) . .
C10 C9 S13 C12 1.5(5) . .
C4 C9 S13 C12 -179.3(5) . .
C11 C12 C14 N18 177.4(6) . .
S13 C12 C14 N18 -0.1(9) . .
C11 C12 C14 N15 -0.1(11) . .
S13 C12 C14 N15 -177.5(5) . .
N18 C14 N15 O19 -179.6(5) . .
C12 C14 N15 O19 -1.8(10) . .
N18 C14 N15 C16 -10.1(7) . .
C12 C14 N15 C16 167.7(6) . .
O19 N15 C16 C21 72.8(7) . .
C14 N15 C16 C21 -97.1(6) . .
O19 N15 C16 C20 -46.2(8) . .
C14 N15 C16 C20 144.0(5) . .
O19 N15 C16 C17 -167.2(5) . .
C14 N15 C16 C17 22.9(6) . .
N15 C16 C17 N18 -25.0(5) . .
C21 C16 C17 N18 88.0(6) . .
C20 C16 C17 N18 -142.5(5) . .
N15 C16 C17 C23 -142.8(5) . .
C21 C16 C17 C23 -29.9(7) . .
C20 C16 C17 C23 99.6(6) . .
N15 C16 C17 C22 89.1(6) . .
C21 C16 C17 C22 -157.9(5) . .
C20 C16 C17 C22 -28.4(8) . .
N15 C14 N18 O24 -179.8(5) . .
C12 C14 N18 O24 2.3(10) . .
N15 C14 N18 C17 -8.5(7) . .
C12 C14 N18 C17 173.6(6) . .
C23 C17 N18 O24 -44.6(8) . .
C22 C17 N18 O24 74.6(7) . .
C16 C17 N18 O24 -166.4(5) . .
C23 C17 N18 C14 143.9(6) . .
C22 C17 N18 C14 -96.9(6) . .
C16 C17 N18 C14 22.1(6) . .
