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#$Date: 2025-08-18 16:20:24 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301776 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/96/1519602.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_1519602
loop_
_publ_author_name
'Hursthouse, Michael B.'
'Huth, Susanne. L.'
_publ_section_title
;
 1,3,8,10-Tetrakis-(4-fluoro-phenyl)-1,3,8,10-tetrahydro-4,5,6,7-tetrathia-
 1,3,8,10-tetraaza-dicyclopenta[a,c]cyclooctene-2,9-dithione
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              30
_journal_year                    2004
_chemical_formula_sum            'C31 H17 Cl3 F4 N4 S6'
_chemical_formula_weight         820.20
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                110.438(4)
_cell_angle_beta                 98.073(4)
_cell_angle_gamma                115.161(4)
_cell_formula_units_Z            2
_cell_length_a                   11.3216(3)
_cell_length_b                   13.2873(6)
_cell_length_c                   13.9320(9)
_cell_measurement_reflns_used    43156
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1671.26(18)
_computing_cell_refinement       'DENZO & COLLECT'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO & COLLECT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33949
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  0.9459
_exptl_absorpt_correction_T_min  0.8958
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.810
_refine_diff_density_min         -0.779
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.669
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         7667
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.674
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.503
_refine_ls_shift/su_mean         0.013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0690P)²+6.3898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1038
_reflns_number_gt                6356
_reflns_number_total             7667
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-30.cif
_cod_data_source_block           04alb001
_cod_depositor_comments
;
Citation :
Hursthouse, Michael B. and Huth, Susanne. L. (2004) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/30)

More at:
http://ecrystals.chem.soton.ac.uk/30/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_cell_volume        1671.26(14)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1519602
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3852(2) 0.6253(2) 0.16486(17) 0.0171(4) Uani 1 1 d . . .
C2 C 0.4137(2) 0.66693(19) 0.34224(17) 0.0149(4) Uani 1 1 d . . .
C3 C 0.3181(2) 0.69491(19) 0.30895(16) 0.0144(4) Uani 1 1 d . . .
C4 C 0.2511(2) 0.74845(18) 0.37371(16) 0.0139(4) Uani 1 1 d . . .
C5 C 0.1703(2) 0.70197(18) 0.42879(16) 0.0141(4) Uani 1 1 d . . .
C6 C 0.2016(2) 0.89457(19) 0.46808(16) 0.0146(4) Uani 1 1 d . . .
C7 C 0.2059(2) 0.6827(2) 0.13313(17) 0.0176(4) Uani 1 1 d . . .
C8 C 0.0686(2) 0.6296(2) 0.12753(19) 0.0217(4) Uani 1 1 d . . .
C9 C -0.0242(3) 0.6396(3) 0.0604(2) 0.0303(5) Uani 1 1 d . . .
C10 C 0.0246(3) 0.7008(3) 0.0005(2) 0.0352(6) Uani 1 1 d . . .
C11 C 0.1606(3) 0.7555(3) 0.0059(2) 0.0330(6) Uani 1 1 d . . .
C12 C 0.2535(3) 0.7468(2) 0.07386(19) 0.0246(5) Uani 1 1 d . . .
C13 C 0.5458(2) 0.5761(2) 0.24911(17) 0.0176(4) Uani 1 1 d . . .
C14 C 0.6829(2) 0.6537(2) 0.2644(2) 0.0255(5) Uani 1 1 d . . .
C15 C 0.7710(3) 0.6061(3) 0.2550(2) 0.0325(6) Uani 1 1 d . . .
C16 C 0.7182(3) 0.4832(3) 0.2311(2) 0.0321(6) Uani 1 1 d . . .
C17 C 0.5839(3) 0.4056(3) 0.2168(2) 0.0347(6) Uani 1 1 d . . .
C18 C 0.4951(3) 0.4527(2) 0.2258(2) 0.0270(5) Uani 1 1 d . . .
C19 C 0.0582(2) 0.78305(19) 0.55647(17) 0.0153(4) Uani 1 1 d . . .
C20 C 0.0909(2) 0.75713(19) 0.64133(17) 0.0165(4) Uani 1 1 d . . .
C21 C 0.0120(2) 0.7507(2) 0.70932(18) 0.0193(4) Uani 1 1 d . . .
C22 C -0.0963(2) 0.7713(2) 0.69025(18) 0.0208(4) Uani 1 1 d . . .
C23 C -0.1305(2) 0.7973(2) 0.60652(19) 0.0212(4) Uani 1 1 d . . .
C24 C -0.0520(2) 0.8031(2) 0.53876(18) 0.0178(4) Uani 1 1 d . . .
C25 C 0.3422(2) 0.94291(19) 0.35071(16) 0.0155(4) Uani 1 1 d . . .
C26 C 0.2780(2) 0.9857(2) 0.29620(18) 0.0188(4) Uani 1 1 d . . .
C27 C 0.3504(3) 1.0568(2) 0.24867(19) 0.0233(5) Uani 1 1 d . . .
C28 C 0.4831(3) 1.0800(2) 0.25670(19) 0.0224(5) Uani 1 1 d . . .
C29 C 0.5474(2) 1.0370(2) 0.30886(18) 0.0202(4) Uani 1 1 d . . .
C30 C 0.4762(2) 0.96883(19) 0.35851(17) 0.0163(4) Uani 1 1 d . . .
N1 N 0.30112(18) 0.67012(16) 0.20068(14) 0.0157(3) Uani 1 1 d . . .
N2 N 0.45335(18) 0.62370(17) 0.25341(14) 0.0165(3) Uani 1 1 d . . .
N3 N 0.13972(18) 0.79215(16) 0.48666(14) 0.0146(3) Uani 1 1 d . . .
N4 N 0.26632(18) 0.86463(16) 0.39569(14) 0.0145(3) Uani 1 1 d . . .
S1 S 0.09363(5) 0.54996(5) 0.41202(4) 0.01562(11) Uani 1 1 d . . .
S2 S 0.22755(5) 0.55880(5) 0.53695(4) 0.01808(12) Uani 1 1 d . . .
S3 S 0.36991(6) 0.53138(5) 0.47535(5) 0.01902(12) Uani 1 1 d . . .
S4 S 0.49565(5) 0.69719(5) 0.47225(4) 0.01694(12) Uani 1 1 d . . .
S5 S 0.40138(6) 0.57953(6) 0.04310(5) 0.02475(13) Uani 1 1 d . . .
S6 S 0.20874(6) 1.03064(5) 0.52690(5) 0.01975(12) Uani 1 1 d . . .
F1 F -0.0670(2) 0.7052(2) -0.06963(15) 0.0575(6) Uani 1 1 d . . .
F2 F 0.8044(2) 0.4367(2) 0.22077(14) 0.0501(5) Uani 1 1 d . . .
F3 F -0.17253(15) 0.76670(14) 0.75700(12) 0.0303(3) Uani 1 1 d . . .
F4 F 0.55372(16) 1.14733(14) 0.20888(13) 0.0325(3) Uani 1 1 d . . .
H8 H 0.040(3) 0.585(2) 0.167(2) 0.016(6) Uiso 1 1 d . . .
H9 H -0.121(3) 0.601(3) 0.053(3) 0.036(8) Uiso 1 1 d . . .
H11 H 0.190(4) 0.797(3) -0.035(3) 0.048(9) Uiso 1 1 d . . .
H12 H 0.346(3) 0.782(3) 0.081(2) 0.029(7) Uiso 1 1 d . . .
H14 H 0.713(3) 0.738(3) 0.278(2) 0.034(8) Uiso 1 1 d . . .
H15 H 0.870(4) 0.660(3) 0.266(3) 0.044(9) Uiso 1 1 d . . .
H17 H 0.551(4) 0.323(3) 0.202(3) 0.052(10) Uiso 1 1 d . . .
H18 H 0.399(3) 0.400(3) 0.217(2) 0.035(8) Uiso 1 1 d . . .
H20 H 0.166(3) 0.746(2) 0.655(2) 0.016(6) Uiso 1 1 d . . .
H21 H 0.030(3) 0.730(3) 0.763(2) 0.024(7) Uiso 1 1 d . . .
H23 H -0.210(3) 0.807(3) 0.592(2) 0.031(7) Uiso 1 1 d . . .
H24 H -0.074(3) 0.821(2) 0.480(2) 0.019(6) Uiso 1 1 d . . .
H26 H 0.187(3) 0.966(2) 0.294(2) 0.017(6) Uiso 1 1 d . . .
H27 H 0.309(3) 1.086(3) 0.211(2) 0.027(7) Uiso 1 1 d . . .
H29 H 0.636(3) 1.050(2) 0.310(2) 0.021(6) Uiso 1 1 d . . .
H30 H 0.516(3) 0.936(2) 0.397(2) 0.018(6) Uiso 1 1 d . . .
C311 C 0.3046(5) 0.1389(5) 0.9354(4) 0.0395(11) Uani 0.759(4) 1 d PD A 1
H311 H 0.3761 0.2294 0.9660 0.047 Uiso 0.759(4) 1 calc PR A 1
Cl31 Cl 0.1941(2) 0.1246(2) 1.01153(17) 0.0713(6) Uani 0.759(4) 1 d PD A 1
Cl32 Cl 0.38949(13) 0.05854(14) 0.95101(10) 0.0479(4) Uani 0.759(4) 1 d PD A 1
Cl33 Cl 0.22038(14) 0.08378(10) 0.79821(8) 0.0464(4) Uani 0.759(4) 1 d PD A 1
C411 C 0.270(2) 0.144(2) 0.9365(17) 0.39(6) Uani 0.241(4) 1 d PD A 2
H411 H 0.3233 0.2365 0.9815 0.466 Uiso 0.241(4) 1 calc PR A 2
Cl41 Cl 0.357(3) 0.0707(19) 0.959(2) 0.48(3) Uani 0.241(4) 1 d PD A 2
Cl42 Cl 0.194(3) 0.0953(19) 0.8050(17) 0.50(3) Uani 0.241(4) 1 d PD A 2
Cl43 Cl 0.1258(15) 0.0677(15) 0.9682(10) 0.181(6) Uani 0.241(4) 1 d PD A 2
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'
F F 0.0171 0.0103 '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'
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
N2 C1 N1 104.54(17) . .
N2 C1 S5 126.03(16) . .
N1 C1 S5 129.42(16) . .
C3 C2 N2 106.95(18) . .
C3 C2 S4 129.26(16) . .
N2 C2 S4 123.17(15) . .
C2 C3 N1 107.36(17) . .
C2 C3 C4 127.58(19) . .
N1 C3 C4 124.95(18) . .
C5 C4 N4 107.13(17) . .
C5 C4 C3 128.41(18) . .
N4 C4 C3 124.36(18) . .
C4 C5 N3 107.19(17) . .
C4 C5 S1 126.43(15) . .
N3 C5 S1 125.45(15) . .
N4 C6 N3 105.24(17) . .
N4 C6 S6 126.45(15) . .
N3 C6 S6 128.16(16) . .
C8 C7 C12 121.6(2) . .
C8 C7 N1 119.40(19) . .
C12 C7 N1 119.0(2) . .
C7 C8 C9 119.4(2) . .
C7 C8 H8 119.3(16) . .
C9 C8 H8 121.3(16) . .
C10 C9 C8 117.9(2) . .
C10 C9 H9 120.5(19) . .
C8 C9 H9 121.5(19) . .
F1 C10 C11 118.1(3) . .
F1 C10 C9 118.3(3) . .
C11 C10 C9 123.6(2) . .
C10 C11 C12 118.4(2) . .
C10 C11 H11 121(2) . .
C12 C11 H11 120(2) . .
C11 C12 C7 119.1(2) . .
C11 C12 H12 121.9(18) . .
C7 C12 H12 119.0(18) . .
C18 C13 C14 121.4(2) . .
C18 C13 N2 119.3(2) . .
C14 C13 N2 119.2(2) . .
C13 C14 C15 119.4(2) . .
C13 C14 H14 118.8(18) . .
C15 C14 H14 121.8(18) . .
C16 C15 C14 118.3(2) . .
C16 C15 H15 121(2) . .
C14 C15 H15 121(2) . .
F2 C16 C17 118.8(3) . .
F2 C16 C15 118.0(3) . .
C17 C16 C15 123.2(2) . .
C16 C17 C18 118.7(3) . .
C16 C17 H17 121(2) . .
C18 C17 H17 120(2) . .
C13 C18 C17 119.1(2) . .
C13 C18 H18 120.2(18) . .
C17 C18 H18 120.7(18) . .
C20 C19 C24 120.92(19) . .
C20 C19 N3 120.32(18) . .
C24 C19 N3 118.75(18) . .
C19 C20 C21 119.5(2) . .
C19 C20 H20 121.2(16) . .
C21 C20 H20 119.3(16) . .
C22 C21 C20 118.5(2) . .
C22 C21 H21 121.4(17) . .
C20 C21 H21 120.1(18) . .
F3 C22 C21 118.8(2) . .
F3 C22 C23 118.3(2) . .
C21 C22 C23 123.0(2) . .
C22 C23 C24 118.4(2) . .
C22 C23 H23 121.4(18) . .
C24 C23 H23 120.1(18) . .
C23 C24 C19 119.8(2) . .
C23 C24 H24 119.4(16) . .
C19 C24 H24 120.8(16) . .
C30 C25 C26 121.63(19) . .
C30 C25 N4 118.66(18) . .
C26 C25 N4 119.63(19) . .
C25 C26 C27 119.1(2) . .
C25 C26 H26 118.7(16) . .
C27 C26 H26 122.2(16) . .
C28 C27 C26 118.0(2) . .
C28 C27 H27 121.4(18) . .
C26 C27 H27 120.6(18) . .
F4 C28 C29 117.9(2) . .
F4 C28 C27 118.5(2) . .
C29 C28 C27 123.6(2) . .
C28 C29 C30 118.2(2) . .
C28 C29 H29 122.2(17) . .
C30 C29 H29 119.6(17) . .
C25 C30 C29 119.4(2) . .
C25 C30 H30 118.7(15) . .
C29 C30 H30 121.9(15) . .
C1 N1 C3 110.27(17) . .
C1 N1 C7 124.11(17) . .
C3 N1 C7 125.56(17) . .
C1 N2 C2 110.88(17) . .
C1 N2 C13 122.65(17) . .
C2 N2 C13 126.37(17) . .
C6 N3 C5 109.88(16) . .
C6 N3 C19 123.74(17) . .
C5 N3 C19 126.38(17) . .
C6 N4 C4 110.48(16) . .
C6 N4 C25 125.12(17) . .
C4 N4 C25 124.38(17) . .
C5 S1 S2 104.22(7) . .
S3 S2 S1 105.21(3) . .
S2 S3 S4 104.78(3) . .
C2 S4 S3 101.68(7) . .
Cl33 C311 Cl31 113.6(3) . .
Cl33 C311 Cl32 110.2(3) . .
Cl31 C311 Cl32 108.1(3) . .
Cl33 C311 H311 108.3 . .
Cl31 C311 H311 108.3 . .
Cl32 C311 H311 108.3 . .
Cl42 C411 Cl41 113.5(18) . .
Cl42 C411 Cl43 99.8(14) . .
Cl41 C411 Cl43 99.1(17) . .
Cl42 C411 H411 114.2 . .
Cl41 C411 H411 114.3 . .
Cl43 C411 H411 114.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.372(3) .
C1 N1 1.385(3) .
C1 S5 1.656(2) .
C2 C3 1.359(3) .
C2 N2 1.394(3) .
C2 S4 1.734(2) .
C3 N1 1.392(3) .
C3 C4 1.449(3) .
C4 C5 1.362(3) .
C4 N4 1.391(3) .
C5 N3 1.401(2) .
C5 S1 1.735(2) .
C6 N4 1.374(3) .
C6 N3 1.377(3) .
C6 S6 1.664(2) .
C7 C8 1.384(3) .
C7 C12 1.387(3) .
C7 N1 1.433(3) .
C8 C9 1.388(3) .
C8 H8 0.93(3) .
C9 C10 1.373(4) .
C9 H9 0.96(3) .
C10 F1 1.357(3) .
C10 C11 1.372(4) .
C11 C12 1.384(3) .
C11 H11 0.92(4) .
C12 H12 0.92(3) .
C13 C18 1.377(3) .
C13 C14 1.382(3) .
C13 N2 1.434(3) .
C14 C15 1.388(3) .
C14 H14 0.96(3) .
C15 C16 1.368(4) .
C15 H15 0.99(3) .
C16 F2 1.358(3) .
C16 C17 1.361(4) .
C17 C18 1.390(3) .
C17 H17 0.93(4) .
C18 H18 0.97(3) .
C19 C20 1.387(3) .
C19 C24 1.389(3) .
C19 N3 1.432(3) .
C20 C21 1.390(3) .
C20 H20 0.92(3) .
C21 C22 1.376(3) .
C21 H21 0.91(3) .
C22 F3 1.354(2) .
C22 C23 1.377(3) .
C23 C24 1.384(3) .
C23 H23 0.96(3) .
C24 H24 0.97(3) .
C25 C30 1.384(3) .
C25 C26 1.388(3) .
C25 N4 1.435(3) .
C26 C27 1.391(3) .
C26 H26 0.94(3) .
C27 C28 1.379(3) .
C27 H27 0.93(3) .
C28 F4 1.356(2) .
C28 C29 1.371(3) .
C29 C30 1.387(3) .
C29 H29 0.93(3) .
C30 H30 0.97(3) .
S1 S2 2.0752(7) .
S2 S3 2.0338(7) .
S3 S4 2.0734(8) .
C311 Cl33 1.736(5) .
C311 Cl31 1.743(5) .
C311 Cl32 1.758(4) .
C311 H311 1.0000 .
C411 Cl42 1.666(18) .
C411 Cl41 1.72(2) .
C411 Cl43 1.726(18) .
C411 H411 1.0000 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139045165
