#------------------------------------------------------------------------------
#$Date: 2020-02-04 22:03:57 +0200 (Tue, 04 Feb 2020) $
#$Revision: 247589 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/58/7125807.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_7125807
loop_
_publ_author_name
'Makarov, Alexander Yu'
'Volkova, Yulia M.'
'Shundrin, Leonid A.'
'Dmitriev, Alexey A.'
'Irtegova, Irina G.'
'Bagryanskaya, Irina Yu'
'Shundrina, Inna K.'
'Gritsan, Nina P.'
'Beckmann, Jens'
'Zibarev, Andrey V.'
_publ_section_title
;
 Chemistry of Herz radicals: a new way to near-IR dyes with multiple
 long-lived and differently-coloured redox states.
;
_journal_issue                   5
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              727
_journal_page_last               730
_journal_paper_doi               10.1039/c9cc08557b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C20 H20 N4 S5 [+ solvent]'
_chemical_formula_sum            'C20 H20 N4 S5'
_chemical_formula_weight         476.70
_chemical_name_systematic
'4,7-di-tert-butylbis[1,2,3]dithiazolo[4'5':3,4;5',4':8,9]dibenzo [c,e][1?4?2,2,7]thiadiazepine'
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-10-17 deposited with the CCDC.	2019-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 120.32(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.008(5)
_cell_length_b                   7.0295(14)
_cell_length_c                   14.980(3)
_cell_measurement_reflns_used    3089
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.86
_cell_measurement_theta_min      2.73
_cell_volume                     2364.1(11)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0959
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23626
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         2.729
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.8821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2941
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0479
_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)+(0.0609P)²+0.8543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1272
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1878
_reflns_number_total             2941
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc08557b2.cif
_cod_data_source_block           2_m675
_cod_depositor_comments
'Adding full bibliography for 7125802--7125809.cif.'
_cod_original_cell_volume        2364.1(10)
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7125807
_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   0.660
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
S2 S 0.23859(5) 0.0000 0.22593(8) 0.0348(3) Uani 1 2 d S T P
S5 S 0.35718(4) 0.0000 0.11311(8) 0.0347(3) Uani 1 2 d S T P
S1 S 0.15573(5) 0.0000 0.21568(8) 0.0417(3) Uani 1 2 d S T P
S4 S 0.39595(4) 0.0000 -0.12714(8) 0.0374(3) Uani 1 2 d S T P
S3 S 0.37628(5) 0.0000 -0.28001(9) 0.0471(3) Uani 1 2 d S T P
C7 C 0.32085(15) 0.0000 -0.1657(3) 0.0255(8) Uani 1 2 d S T P
C1 C 0.14151(17) 0.0000 0.0370(3) 0.0264(8) Uani 1 2 d S T P
N1 N 0.11312(15) 0.0000 0.0895(2) 0.0352(8) Uani 1 2 d S T P
C3 C 0.24093(15) 0.0000 0.0473(3) 0.0233(8) Uani 1 2 d S T P
C6 C 0.30312(16) 0.0000 -0.0920(3) 0.0241(8) Uani 1 2 d S T P
N4 N 0.30086(13) 0.0000 0.1229(2) 0.0299(7) Uani 1 2 d S T P
C5 C 0.24000(15) 0.0000 -0.1266(3) 0.0222(8) Uani 1 2 d S T P
C8 C 0.28079(17) 0.0000 -0.2763(3) 0.0286(9) Uani 1 2 d S T P
C9 C 0.21788(17) 0.0000 -0.3125(3) 0.0301(9) Uani 1 2 d S T P
C16 C 0.17134(19) 0.0000 -0.4280(3) 0.0470(12) Uani 1 2 d S T P
C2 C 0.20547(17) 0.0000 0.0921(3) 0.0252(8) Uani 1 2 d S T P
N3 N 0.35219(14) 0.0000 0.0061(3) 0.0350(8) Uani 1 2 d S T P
C12 C 0.11172(17) 0.0000 -0.0742(3) 0.0289(8) Uani 1 2 d S T P
N2 N 0.30337(15) 0.0000 -0.3382(3) 0.0390(8) Uani 1 2 d S T P
C4 C 0.21250(15) 0.0000 -0.0642(3) 0.0226(8) Uani 1 2 d S T P
C11 C 0.14791(17) 0.0000 -0.1164(3) 0.0303(9) Uani 1 2 d DS T P
C10 C 0.20213(18) 0.0000 -0.2385(3) 0.0306(9) Uani 1 2 d DS T P
C18 C 0.1074(2) 0.0000 -0.4468(4) 0.075(2) Uani 1 2 d DS T P
C13 C 0.04353(16) 0.0000 -0.1422(3) 0.0365(10) Uani 1 2 d S T P
C14 C 0.01743(13) 0.1771(5) -0.1198(3) 0.0516(9) Uani 1 1 d . . .
H14A H 0.0298 0.1807 -0.0477 0.077 Uiso 1 1 calc R U .
H14B H 0.0314 0.2891 -0.1377 0.077 Uiso 1 1 calc R U .
H14C H -0.0253 0.1725 -0.1602 0.077 Uiso 1 1 calc R U .
C15 C 0.0230(3) 0.0000 -0.2565(4) 0.070(2) Uani 1 2 d S T P
C17 C 0.1787(2) 0.1803(8) -0.4785(3) 0.0765(14) Uani 1 1 d . . .
H15A H -0.015(3) 0.0000 -0.287(4) 0.070(17) Uiso 1 2 d S . P
H15B H 0.0340(16) 0.113(5) -0.279(3) 0.067(11) Uiso 1 1 d . . .
H11 H 0.1272(16) 0.0000 -0.1842(9) 0.043(12) Uiso 1 2 d DS . P
H18A H 0.0797(17) 0.0000 -0.5186(10) 0.089(19) Uiso 1 2 d DS . P
H17A H 0.1697(18) 0.317(7) -0.447(3) 0.100(15) Uiso 1 1 d . . .
H17B H 0.1517(19) 0.185(6) -0.543(4) 0.090(14) Uiso 1 1 d . . .
H18B H 0.1023(14) 0.113(3) -0.4166(18) 0.073(12) Uiso 1 1 d D . .
H10 H 0.1632(5) 0.0000 -0.268(3) 0.063(16) Uiso 1 2 d DS . P
H17C H 0.215(2) 0.188(6) -0.473(3) 0.088(15) 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'
N N 0.0061 0.0033 '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
C2 S2 S1 91.33(14) . .
N3 S5 N4 120.83(17) . .
N1 S1 S2 99.06(13) . .
C7 S4 S3 91.33(14) . .
N2 S3 S4 99.27(13) . .
C6 C7 C8 124.9(3) . .
C6 C7 S4 120.2(3) . .
C8 C7 S4 114.9(3) . .
N1 C1 C2 119.4(3) . .
N1 C1 C12 123.5(3) . .
C2 C1 C12 117.1(3) . .
C1 N1 S1 115.5(3) . .
C2 C3 N4 110.7(3) . .
C2 C3 C4 118.8(3) . .
N4 C3 C4 130.6(3) . .
N3 C6 C7 110.3(3) . .
N3 C6 C5 130.8(3) . .
C7 C6 C5 118.9(3) . .
C3 N4 S5 130.6(3) . .
C4 C5 C6 127.8(3) . .
C4 C5 C10 118.7(3) . .
C6 C5 C10 113.4(3) . .
N2 C8 C9 123.8(4) . .
N2 C8 C7 119.0(3) . .
C9 C8 C7 117.2(3) . .
C10 C9 C8 116.4(3) . .
C10 C9 C16 121.9(4) . .
C8 C9 C16 121.7(3) . .
C9 C16 C17 109.4(3) . .
C9 C16 C17 109.4(3) . 6
C17 C16 C17 111.1(5) . 6
C9 C16 C18 111.8(4) . .
C17 C16 C18 107.5(3) . .
C17 C16 C18 107.5(3) 6 .
C3 C2 C1 125.6(3) . .
C3 C2 S2 119.6(3) . .
C1 C2 S2 114.7(3) . .
C6 N3 S5 131.0(3) . .
C11 C12 C1 116.0(3) . .
C11 C12 C13 121.7(4) . .
C1 C12 C13 122.3(3) . .
C8 N2 S3 115.5(3) . .
C5 C4 C3 128.3(3) . .
C5 C4 C11 118.1(3) . .
C3 C4 C11 113.6(3) . .
C12 C11 C4 128.9(4) . .
C9 C10 C5 129.2(4) . .
C15 C13 C12 112.3(4) . .
C15 C13 C14 107.7(2) . 6
C12 C13 C14 110.2(2) . 6
C15 C13 C14 107.7(2) . .
C12 C13 C14 110.2(2) . .
C14 C13 C14 108.5(3) 6 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S2 C2 1.738(4) .
S2 S1 2.0816(16) .
S5 N3 1.541(3) .
S5 N4 1.544(3) .
S1 N1 1.638(3) .
S4 C7 1.735(4) .
S4 S3 2.0792(17) .
S3 N2 1.639(4) .
C7 C6 1.396(5) .
C7 C8 1.444(5) .
C1 N1 1.323(5) .
C1 C2 1.436(5) .
C1 C12 1.439(5) .
C3 C2 1.387(5) .
C3 N4 1.389(4) .
C3 C4 1.446(5) .
C6 N3 1.377(5) .
C6 C5 1.451(5) .
C5 C4 1.435(5) .
C5 C10 1.454(5) .
C8 N2 1.325(5) .
C8 C9 1.441(5) .
C9 C10 1.361(5) .
C9 C16 1.531(6) .
C16 C17 1.537(5) .
C16 C17 1.537(5) 6
C16 C18 1.540(7) .
C12 C11 1.374(5) .
C12 C13 1.536(5) .
C4 C11 1.452(5) .
C13 C15 1.514(7) .
C13 C14 1.534(4) 6
C13 C14 1.534(4) .
