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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/17/1501774.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_1501774
loop_
_publ_author_name
'von Eschwege, Karel G.'
'Conradie, Jeanet'
'Kuhn, Annemarie'
_publ_section_title
;
 Dithizone and Its oxidation products: a DFT, spectroscopic, and X-ray
 structural study.
;
_journal_issue                   51
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              14637
_journal_page_last               14646
_journal_paper_doi               10.1021/jp208212e
_journal_volume                  115
_journal_year                    2011
_chemical_formula_sum            'C29 H25 F4 N8 S2'
_chemical_formula_weight         627.70
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.674(2)
_cell_angle_beta                 85.270(2)
_cell_angle_gamma                76.176(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6537(3)
_cell_length_b                   12.4352(6)
_cell_length_c                   16.3279(7)
_cell_measurement_temperature    100(2)
_cell_volume                     1447.96(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26267
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.30
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_correction_T_min  0.9190
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             650
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         7145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1221P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.2182
_reflns_number_gt                4637
_reflns_number_total             7145
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp208212e_si_002.cif
_cod_data_source_block           9lak1_0m
_cod_original_formula_sum        'C14.50 H13.50 F2 N4 S'
_cod_database_code               1501774
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.94896(10) 0.73992(7) 0.15784(5) 0.0277(2) Uani 1 1 d .
S2 S 1.18017(10) 0.60789(6) 0.17684(4) 0.0249(2) Uani 1 1 d .
F1 F 1.1280(2) 0.46370(15) -0.05985(10) 0.0278(4) Uani 1 1 d .
F2 F 1.3764(3) 0.80589(18) 0.34847(11) 0.0403(5) Uani 1 1 d .
N3 N 1.2858(3) 0.5989(2) -0.00156(15) 0.0243(5) Uani 1 1 d .
H3 H 1.2088 0.5631 0.0315 0.029 Uiso 1 1 calc R
F4 F 0.9097(3) 0.40164(17) 0.37816(12) 0.0476(6) Uani 1 1 d .
F5 F 1.1636(3) 1.06392(19) 0.03038(12) 0.0504(6) Uani 1 1 d .
N6 N 1.3878(3) 0.7717(2) 0.19237(15) 0.0257(5) Uani 1 1 d .
N7 N 1.3664(3) 0.6647(2) 0.02545(15) 0.0249(5) Uani 1 1 d .
C8 C 1.3313(4) 0.6767(3) 0.10282(18) 0.0245(6) Uani 1 1 d .
N9 N 0.8949(3) 0.7315(2) 0.33085(16) 0.0298(6) Uani 1 1 d .
N10 N 0.9762(3) 0.8904(2) 0.24916(15) 0.0290(6) Uani 1 1 d .
C11 C 1.2441(4) 0.5185(3) -0.11424(17) 0.0229(6) Uani 1 1 d .
N12 N 1.4191(3) 0.7546(2) 0.11862(15) 0.0250(5) Uani 1 1 d .
C13 C 1.5361(4) 0.9372(3) 0.13710(19) 0.0270(6) Uani 1 1 d .
H13 H 1.5500 0.9265 0.0814 0.032 Uiso 1 1 calc R
N14 N 1.0276(3) 0.9518(2) 0.17606(15) 0.0293(6) Uani 1 1 d .
H14 H 1.0430 0.9251 0.1309 0.035 Uiso 1 1 calc R
N15 N 0.8743(3) 0.6326(2) 0.33567(16) 0.0302(6) Uani 1 1 d .
C16 C 1.3261(4) 0.5877(3) -0.08424(17) 0.0231(6) Uani 1 1 d .
C17 C 1.4626(4) 0.8608(3) 0.20291(18) 0.0254(6) Uani 1 1 d .
C18 C 1.2753(4) 0.5026(3) -0.19436(18) 0.0259(6) Uani 1 1 d .
H18 H 1.2152 0.4552 -0.2128 0.031 Uiso 1 1 calc R
C19 C 1.4820(4) 0.6267(3) -0.21943(19) 0.0302(7) Uani 1 1 d .
H19 H 1.5658 0.6635 -0.2561 0.036 Uiso 1 1 calc R
C20 C 1.4469(4) 0.6431(3) -0.13862(18) 0.0261(6) Uani 1 1 d .
H20 H 1.5048 0.6918 -0.1204 0.031 Uiso 1 1 calc R
C21 C 1.5887(4) 1.0282(3) 0.1532(2) 0.0314(7) Uani 1 1 d .
H21 H 1.6380 1.0802 0.1082 0.038 Uiso 1 1 calc R
C22 C 1.0585(4) 1.0622(3) 0.1702(2) 0.0305(7) Uani 1 1 d .
C23 C 0.9442(4) 0.7910(3) 0.2511(2) 0.0276(7) Uani 1 1 d .
C24 C 1.3963(4) 0.5571(3) -0.24775(18) 0.0286(7) Uani 1 1 d .
H24 H 1.4208 0.5471 -0.3035 0.034 Uiso 1 1 calc R
C25 C 1.4472(4) 0.8787(3) 0.28338(19) 0.0283(7) Uani 1 1 d .
C26 C 1.5699(4) 1.0441(3) 0.2343(2) 0.0312(7) Uani 1 1 d .
H26 H 1.6055 1.1073 0.2445 0.037 Uiso 1 1 calc R
C27 C 0.7106(4) 0.4493(3) 0.5768(2) 0.0376(8) Uani 1 1 d .
H27 H 0.6726 0.4070 0.6305 0.045 Uiso 1 1 calc R
C28 C 0.8180(4) 0.5740(3) 0.41917(18) 0.0292(7) Uani 1 1 d .
C29 C 1.1631(5) 1.2250(3) 0.0806(2) 0.0418(9) Uani 1 1 d .
H29 H 1.2121 1.2610 0.0274 0.050 Uiso 1 1 calc R
C30 C 1.4997(4) 0.9688(3) 0.3007(2) 0.0321(7) Uani 1 1 d .
H30 H 1.4879 0.9787 0.3566 0.039 Uiso 1 1 calc R
C31 C 0.8339(4) 0.4576(3) 0.4371(2) 0.0346(8) Uani 1 1 d .
C32 C 1.1258(4) 1.1188(3) 0.0947(2) 0.0329(7) Uani 1 1 d .
C34 C 0.6951(5) 0.5659(3) 0.5604(2) 0.0433(9) Uani 1 1 d .
H34 H 0.6482 0.6035 0.6033 0.052 Uiso 1 1 calc R
C35 C 1.0594(5) 1.2234(3) 0.2230(3) 0.0446(9) Uani 1 1 d .
H35 H 1.0363 1.2599 0.2679 0.054 Uiso 1 1 calc R
C36 C 0.7814(5) 0.3936(3) 0.5151(2) 0.0395(8) Uani 1 1 d .
H36 H 0.7937 0.3130 0.5260 0.047 Uiso 1 1 calc R
C38 C 0.7474(5) 0.6293(3) 0.4815(2) 0.0383(8) Uani 1 1 d .
H38 H 0.7350 0.7100 0.4704 0.046 Uiso 1 1 calc R
C39 C 1.0245(4) 1.1149(3) 0.2355(2) 0.0386(8) Uani 1 1 d .
H39 H 0.9775 1.0774 0.2888 0.046 Uiso 1 1 calc R
C40 C 1.1275(4) 1.2782(3) 0.1455(3) 0.0458(10) Uani 1 1 d .
H40 H 1.1498 1.3526 0.1371 0.055 Uiso 1 1 calc R
C1 C 0.7535(5) 1.0418(3) 0.4588(2) 0.0406(8) Uani 1 1 d .
H1A H 0.7806 1.0085 0.4096 0.049 Uiso 1 1 calc R
H1B H 0.7011 0.9875 0.5051 0.049 Uiso 1 1 calc R
C2 C 0.9288(5) 1.0554(3) 0.4896(2) 0.0415(8) Uani 1 1 d .
H2A H 0.9764 1.1138 0.4448 0.050 Uiso 1 1 calc R
H2B H 0.9025 1.0839 0.5412 0.050 Uiso 1 1 calc R
C3 C 0.6164(5) 1.1554(3) 0.4327(2) 0.0478(9) Uani 1 1 d .
H3A H 0.5070 1.1426 0.4134 0.072 Uiso 1 1 calc R
H3B H 0.6667 1.2091 0.3861 0.072 Uiso 1 1 calc R
H3C H 0.5869 1.1879 0.4816 0.072 Uiso 1 1 calc R
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'
F F 0.0171 0.0103 '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
C23 S1 S2 101.96(10) .
C8 S2 S1 100.24(10) .
N7 N3 C16 118.0(2) .
N12 N6 C17 113.2(2) .
C8 N7 N3 119.4(2) .
N7 C8 N12 111.6(2) .
N7 C8 S2 124.4(2) .
N12 C8 S2 124.0(2) .
N15 N9 C23 114.7(3) .
C23 N10 N14 117.6(3) .
F1 C11 C18 119.6(2) .
F1 C11 C16 117.1(2) .
C18 C11 C16 123.3(3) .
N6 N12 C8 114.7(2) .
C21 C13 C17 120.0(3) .
N10 N14 C22 119.6(3) .
N9 N15 C28 113.3(3) .
C11 C16 C20 117.9(3) .
C11 C16 N3 119.3(3) .
C20 C16 N3 122.8(3) .
C25 C17 C13 118.1(3) .
C25 C17 N6 116.8(3) .
C13 C17 N6 125.0(3) .
C11 C18 C24 118.6(3) .
C20 C19 C24 121.1(3) .
C19 C20 C16 119.6(3) .
C13 C21 C26 120.4(3) .
C32 C22 C39 118.4(3) .
C32 C22 N14 117.3(3) .
C39 C22 N14 124.3(3) .
N10 C23 N9 113.4(3) .
N10 C23 S1 123.7(2) .
N9 C23 S1 122.7(2) .
C18 C24 C19 119.6(3) .
F2 C25 C30 117.9(3) .
F2 C25 C17 119.3(3) .
C30 C25 C17 122.8(3) .
C30 C26 C21 120.5(3) .
C34 C27 C36 120.0(3) .
C31 C28 C38 118.8(3) .
C31 C28 N15 117.7(3) .
C38 C28 N15 123.5(3) .
C32 C29 C40 118.2(3) .
C25 C30 C26 118.2(3) .
F4 C31 C28 119.4(3) .
F4 C31 C36 118.3(3) .
C28 C31 C36 122.2(3) .
C22 C32 C29 123.4(3) .
C22 C32 F5 117.9(3) .
C29 C32 F5 118.7(3) .
C27 C34 C38 120.7(3) .
C40 C35 C39 120.3(4) .
C27 C36 C31 118.7(3) .
C28 C38 C34 119.6(3) .
C22 C39 C35 119.6(3) .
C29 C40 C35 120.0(3) .
C3 C1 C2 112.4(3) .
C2 C2 C1 113.1(4) 2_776
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C23 1.802(3) .
S1 S2 2.0830(11) .
S2 C8 1.787(3) .
F1 C11 1.364(3) .
F2 C25 1.357(4) .
N3 N7 1.317(3) .
N3 C16 1.398(3) .
F4 C31 1.357(4) .
F5 C32 1.382(4) .
N6 N12 1.275(3) .
N6 C17 1.419(4) .
N7 C8 1.312(4) .
C8 N12 1.391(4) .
N9 N15 1.258(4) .
N9 C23 1.377(4) .
N10 C23 1.307(4) .
N10 N14 1.311(3) .
C11 C18 1.370(4) .
C11 C16 1.386(4) .
C13 C21 1.384(4) .
C13 C17 1.398(4) .
N14 C22 1.423(4) .
N15 C28 1.438(4) .
C16 C20 1.394(4) .
C17 C25 1.384(4) .
C18 C24 1.382(4) .
C19 C20 1.386(4) .
C19 C24 1.393(4) .
C21 C26 1.385(4) .
C22 C32 1.365(4) .
C22 C39 1.378(5) .
C25 C30 1.381(4) .
C26 C30 1.384(4) .
C27 C34 1.376(5) .
C27 C36 1.382(5) .
C28 C31 1.371(5) .
C28 C38 1.388(4) .
C29 C32 1.369(5) .
C29 C40 1.378(5) .
C31 C36 1.384(5) .
C34 C38 1.391(5) .
C35 C40 1.383(5) .
C35 C39 1.394(5) .
C1 C3 1.518(5) .
C1 C2 1.533(5) .
C2 C2 1.510(7) 2_776
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037035
