#------------------------------------------------------------------------------
#$Date: 2020-02-04 22:03:57 +0200 (Tue, 04 Feb 2020) $
#$Revision: 247589 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/58/7125806.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_7125806
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 H18 N4 S4, Cl4 Ga'
_chemical_formula_sum            'C20 H18 Cl4 Ga N4 S4'
_chemical_formula_weight         654.14
_chemical_name_systematic
;
 C20 H18 N4 S4, Cl4 Ga
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-I 2y'
_space_group_name_H-M_alt        'I 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_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                 100.258(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6419(11)
_cell_length_b                   6.7683(5)
_cell_length_c                   25.762(3)
_cell_measurement_reflns_used    5386
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.90
_cell_measurement_theta_min      3.76
_cell_volume                     2683.8(4)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0568
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            21368
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         3.115
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.753
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.8055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1316
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.004
_refine_diff_density_min         -1.299
_refine_diff_density_rms         0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0961
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1290P)²+65.1111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2633
_refine_ls_wR_factor_ref         0.2951
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1962
_reflns_number_total             2577
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc08557b2.cif
_cod_data_source_block           1_GaCl4_m632
_cod_depositor_comments
'Adding full bibliography for 7125802--7125809.cif.'
_cod_original_sg_symbol_H-M      'I 2/m'
_cod_database_code               7125806
_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   0.301
_shelx_estimated_absorpt_t_max   0.966
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -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
Cl4 Cl 0.5872(7) 0.8884(16) 0.6805(7) 0.192(6) Uani 0.5 1 d . . P . .
Ga1 Ga 0.56199(16) 0.5769(4) 0.67074(10) 0.0736(9) Uani 0.5 1 d . . P A 1
Cl1 Cl 0.6088(3) 0.5000 0.60407(17) 0.105(2) Uani 0.5 2 d S T P A 1
Cl2 Cl 0.4260(3) 0.5000 0.6607(2) 0.0927(15) Uani 0.5 2 d S T P A 1
Cl3 Cl 0.6383(4) 0.5000 0.7406(2) 0.220(6) Uani 0.5 2 d S T P A 1
Cl1A Cl 0.6088(3) 0.5000 0.60407(17) 0.105(2) Uani 0.5 2 d S T P B 2
Cl2A Cl 0.4260(3) 0.5000 0.6607(2) 0.0927(15) Uani 0.5 2 d S T P C 2
Cl3A Cl 0.6383(4) 0.5000 0.7406(2) 0.220(6) Uani 0.5 2 d S T P D 2
S1 S 0.80418(16) 0.5000 0.57832(11) 0.0318(7) Uani 1 2 d S T P . .
S2 S 1.18505(19) 0.5000 0.34036(11) 0.0401(7) Uani 1 2 d S T P . .
N6 N 0.9066(5) 0.5000 0.4904(3) 0.0257(17) Uani 1 2 d S T P . .
N3 N 1.0808(6) 0.5000 0.3247(4) 0.040(2) Uani 1 2 d S T P . .
C6B C 0.9152(6) 0.5000 0.5838(4) 0.025(2) Uani 1 2 d S T P . .
C3A C 1.0357(7) 0.5000 0.3639(4) 0.030(2) Uani 1 2 d S T P . .
C4 C 0.9410(7) 0.5000 0.3551(4) 0.031(2) Uani 1 2 d S T P . .
C5 C 0.9031(6) 0.5000 0.3981(4) 0.031(2) Uani 1 2 d S T P . .
H4A H 0.8427 0.5000 0.3932 0.038 Uiso 1 2 calc R U P . .
C6A C 0.9564(6) 0.5000 0.5403(4) 0.024(2) Uani 1 2 d S T P . .
C5A C 0.9512(6) 0.5000 0.4511(4) 0.024(2) Uani 1 2 d S T P . .
C7 C 0.8887(8) 0.5000 0.2987(5) 0.046(3) Uani 1 2 d S T P . .
C9 C 0.7905(8) 0.5000 0.2998(6) 0.065(4) Uani 1 2 d S T P . .
H14A H 0.7760 0.6148 0.3183 0.097 Uiso 0.5 1 calc R U P . .
H14B H 0.7585 0.5019 0.2644 0.097 Uiso 0.5 2 calc R U P . .
H14C H 0.7757 0.3832 0.3175 0.097 Uiso 0.25 1 calc R U P . .
C8 C 0.9103(7) 0.3175(19) 0.2692(4) 0.074(3) Uani 1 1 d . . . . .
H15A H 0.8968 0.2013 0.2876 0.111 Uiso 1 1 calc R U . . .
H15B H 0.8766 0.3180 0.2342 0.111 Uiso 1 1 calc R U . . .
H15C H 0.9710 0.3180 0.2673 0.111 Uiso 1 1 calc R U . . .
S1' S 0.59872(18) 0.5000 0.86876(11) 0.0356(7) Uani 1 2 d S T P . .
S2' S 0.7297(2) 0.5000 0.86443(12) 0.0444(8) Uani 1 2 d S T P . .
N6' N 0.4724(5) 0.5000 0.9441(3) 0.0280(18) Uani 1 2 d S T P . .
N3' N 0.7693(6) 0.5000 0.9267(4) 0.040(2) Uani 1 2 d S T P . .
C6B' C 0.6226(7) 0.5000 0.9363(4) 0.029(2) Uani 1 2 d S T P . .
C3A' C 0.7122(7) 0.5000 0.9594(4) 0.034(2) Uani 1 2 d S T P . .
C4' C 0.2613(7) 0.5000 0.9844(5) 0.036(2) Uani 1 2 d S T P . .
C5' C 0.3247(7) 0.5000 0.9545(4) 0.035(2) Uani 1 2 d S T P . .
H10A H 0.3083 0.5000 0.9180 0.042 Uiso 1 2 calc R U P . .
C5A' C 0.4150(6) 0.5000 0.9764(4) 0.027(2) Uani 1 2 d S T P . .
C6A' C 0.5573(7) 0.5000 0.9677(4) 0.028(2) Uani 1 2 d S T P . .
C7' C 0.1633(7) 0.5000 0.9583(6) 0.050(3) Uani 1 2 d S T P . .
C9' C 0.1196(7) 0.3135(19) 0.9763(5) 0.079(3) Uani 1 1 d . . . . .
H17A H 0.1263 0.3129 1.0141 0.118 Uiso 1 1 calc R U . . .
H17B H 0.0589 0.3140 0.9612 0.118 Uiso 1 1 calc R U . . .
H17C H 0.1465 0.1978 0.9648 0.118 Uiso 1 1 calc R U . . .
C8' C 0.1522(10) 0.5000 0.8975(6) 0.070(4) Uani 1 2 d S T P . .
H18A H 0.0915 0.5000 0.8824 0.105 Uiso 1 2 calc R U P . .
H18B H 0.1792 0.6158 0.8861 0.105 Uiso 0.25 1 calc R U P . .
H18C H 0.1792 0.3842 0.8861 0.105 Uiso 0.25 1 calc R U P . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga 0.2307 1.6083 '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
Cl4 Cl4 Ga1 168.5(4) 6_575 .
Ga1 Ga1 Cl3 75.24(9) 6_565 .
Ga1 Ga1 Cl1 75.31(8) 6_565 .
Cl3 Ga1 Cl1 115.7(2) . .
Ga1 Ga1 Cl4 168.5(4) 6_565 .
Cl3 Ga1 Cl4 94.6(5) . .
Cl1 Ga1 Cl4 105.2(4) . .
Ga1 Ga1 Cl2 76.06(8) 6_565 .
Cl3 Ga1 Cl2 116.9(2) . .
Cl1 Ga1 Cl2 109.2(2) . .
Cl4 Ga1 Cl2 114.0(3) . .
Ga1 Cl1 Ga1 29.39(17) . 6_565
Ga1 Cl2 Ga1 27.86(16) 6_565 .
Ga1 Cl3 Ga1 29.51(18) 6_565 .
C6B S1 S2 91.0(4) . 5_766
N3 S2 S1 98.7(4) . 5_766
C5A N6 C6A 115.2(8) . .
C3A N3 S2 117.3(8) . .
C6A C6B C3A 120.9(9) . 5_766
C6A C6B S1 122.8(8) . .
C3A C6B S1 116.3(7) 5_766 .
N3 C3A C6B 116.7(9) . 5_766
N3 C3A C4 122.8(10) . .
C6B C3A C4 120.5(9) 5_766 .
C5 C4 C3A 117.1(9) . .
C5 C4 C7 122.7(10) . .
C3A C4 C7 120.1(9) . .
C4 C5 C5A 123.3(9) . .
C4 C5 H4A 118.4 . .
C5A C5 H4A 118.4 . .
C6B C6A N6 119.1(9) . .
C6B C6A C5A 118.7(9) . 5_766
N6 C6A C5A 122.2(8) . 5_766
N6 C5A C6A 122.6(9) . 5_766
N6 C5A C5 117.9(9) . .
C6A C5A C5 119.5(9) 5_766 .
C8 C7 C8 108.9(12) . 6_565
C8 C7 C9 108.7(7) . .
C8 C7 C9 108.7(7) 6_565 .
C8 C7 C4 110.2(7) . .
C8 C7 C4 110.2(7) 6_565 .
C9 C7 C4 110.2(10) . .
C7 C9 H14A 109.5 . .
C7 C9 H14B 109.5 . .
H14A C9 H14B 109.5 . .
C7 C9 H14C 109.5 . .
H14A C9 H14C 109.5 . .
H14B C9 H14C 109.5 . .
C7 C8 H15A 109.5 . .
C7 C8 H15B 109.5 . .
H15A C8 H15B 109.5 . .
C7 C8 H15C 109.5 . .
H15A C8 H15C 109.5 . .
H15B C8 H15C 109.5 . .
C6B' S1' S2' 90.9(4) . .
N3' S2' S1' 98.9(4) . .
C5A' N6' C6A' 115.8(9) . .
C3A' N3' S2' 116.5(8) . .
C6A' C6B' C3A' 121.3(10) . .
C6A' C6B' S1' 122.2(8) . .
C3A' C6B' S1' 116.5(8) . .
N3' C3A' C6B' 117.2(10) . .
N3' C3A' C4' 122.2(10) . 5_667
C6B' C3A' C4' 120.6(9) . 5_667
C5' C4' C3A' 117.6(10) . 5_667
C5' C4' C7' 121.1(11) . .
C3A' C4' C7' 121.3(10) 5_667 .
C4' C5' C5A' 123.3(10) . .
C4' C5' H10A 118.3 . .
C5A' C5' H10A 118.3 . .
N6' C5A' C6A' 121.0(9) . 5_667
N6' C5A' C5' 119.0(10) . .
C6A' C5A' C5' 119.9(9) 5_667 .
N6' C6A' C6B' 119.5(9) . .
N6' C6A' C5A' 123.2(9) . 5_667
C6B' C6A' C5A' 117.2(9) . 5_667
C8' C7' C4' 111.1(11) . .
C8' C7' C9' 109.2(8) . .
C4' C7' C9' 108.9(7) . .
C8' C7' C9' 109.2(8) . 6_565
C4' C7' C9' 108.9(7) . 6_565
C9' C7' C9' 109.6(12) . 6_565
C7' C9' H17A 109.5 . .
C7' C9' H17B 109.5 . .
H17A C9' H17B 109.5 . .
C7' C9' H17C 109.5 . .
H17A C9' H17C 109.5 . .
H17B C9' H17C 109.5 . .
C7' C8' H18A 109.5 . .
C7' C8' H18B 109.5 . .
H18A C8' H18B 109.5 . .
C7' C8' H18C 109.5 . .
H18A C8' H18C 109.5 . .
H18B C8' H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl4 Cl4 1.51(2) 6_575
Cl4 Ga1 2.152(10) .
Ga1 Ga1 1.040(6) 6_565
Ga1 Cl3 2.042(6) .
Ga1 Cl1 2.051(5) .
Ga1 Cl2 2.160(5) .
Cl1 Ga1 2.051(5) 6_565
Cl2 Ga1 2.160(5) 6_565
Cl3 Ga1 2.042(6) 6_565
S1 C6B 1.717(9) .
S1 S2 2.072(4) 5_766
S2 N3 1.609(10) .
S2 S1 2.072(4) 5_766
N6 C5A 1.327(13) .
N6 C6A 1.380(13) .
N3 C3A 1.332(13) .
C6B C6A 1.388(14) .
C6B C3A 1.426(14) 5_766
C3A C6B 1.426(14) 5_766
C3A C4 1.459(15) .
C4 C5 1.345(15) .
C4 C7 1.536(15) .
C5 C5A 1.439(14) .
C5 H4A 0.9300 .
C6A C5A 1.423(13) 5_766
C5A C6A 1.423(13) 5_766
C7 C8 1.518(13) .
C7 C8 1.518(13) 6_565
C7 C9 1.542(18) .
C9 H14A 0.9600 .
C9 H14B 0.9600 .
C9 H14C 0.9600 .
C8 H15A 0.9600 .
C8 H15B 0.9600 .
C8 H15C 0.9600 .
S1' C6B' 1.713(11) .
S1' S2' 2.072(4) .
S2' N3' 1.613(10) .
N6' C5A' 1.328(13) .
N6' C6A' 1.359(13) .
N3' C3A' 1.333(14) .
C6B' C6A' 1.412(14) .
C6B' C3A' 1.421(15) .
C3A' C4' 1.435(16) 5_667
C4' C5' 1.358(16) .
C4' C3A' 1.435(16) 5_667
C4' C7' 1.561(15) .
C5' C5A' 1.425(15) .
C5' H10A 0.9300 .
C5A' C6A' 1.429(14) 5_667
C6A' C5A' 1.429(14) 5_667
C7' C8' 1.55(2) .
C7' C9' 1.545(13) .
C7' C9' 1.545(13) 6_565
C9' H17A 0.9600 .
C9' H17B 0.9600 .
C9' H17C 0.9600 .
C8' H18A 0.9600 .
C8' H18B 0.9600 .
C8' H18C 0.9600 .
