#------------------------------------------------------------------------------
#$Date: 2021-05-27 07:33:13 +0300 (Thu, 27 May 2021) $
#$Revision: 265534 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/29/7242923.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_7242923
loop_
_publ_author_name
'Akhmadiev, Nail S.'
'Mescheryakova, Ekaterina S.'
'Akhmetova, Vnira R.'
'Ibragimov, Askhat G.'
_publ_section_title
;
 Metal-free multicomponent synthesis of novel macrocyclic tetrathiadienes
 with cyano and amino groups
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              18768
_journal_page_last               18775
_journal_paper_doi               10.1039/D1RA02616J
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C24 H22 F2 N4 S4, 4(C2 H6 O S)'
_chemical_formula_sum            'C32 H46 F2 N4 O4 S8'
_chemical_formula_weight         845.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-12-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-20 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                103.820(7)
_cell_angle_beta                 109.146(6)
_cell_angle_gamma                93.699(4)
_cell_formula_units_Z            1
_cell_length_a                   8.1311(4)
_cell_length_b                   11.9456(7)
_cell_length_c                   12.1000(12)
_cell_measurement_reflns_used    2283
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0900
_cell_measurement_theta_min      2.6700
_cell_volume                     1064.98(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1709
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    7.00   43.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480  -19.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega   55.00   87.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480   19.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega    4.00   74.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480   38.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
  4 omega   -7.00   21.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480   19.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega  -54.00   -6.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480  -19.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
  6 omega  -23.00   20.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000   30.0000 43

#__ type_ start__ end____ width___ exp.time_
  7 omega  -20.00   49.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480  -99.0000    0.0000 69

#__ type_ start__ end____ width___ exp.time_
  8 omega  -23.00   17.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000 -150.0000 40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0017184000
_diffrn_orient_matrix_UB_12      -0.0360820000
_diffrn_orient_matrix_UB_13      0.0385529000
_diffrn_orient_matrix_UB_21      -0.0292974000
_diffrn_orient_matrix_UB_22      -0.0498175000
_diffrn_orient_matrix_UB_23      -0.0511756000
_diffrn_orient_matrix_UB_31      0.0887591000
_diffrn_orient_matrix_UB_32      -0.0069894000
_diffrn_orient_matrix_UB_33      0.0079543000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8840
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.199
_diffrn_reflns_theta_min         2.186
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.466
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       prizm
_exptl_crystal_F_000             444
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4905
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      0.875
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1572
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3195
_reflns_number_total             4905
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra02616j2.cif
_cod_data_source_block           ans-687
_cod_original_cell_volume        1064.98(14)
_cod_database_code               7242923
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Rigid body (RIGU) restrains
 S3A, S3, O2, C16, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(S3A)=1-FVAR(1)
 Sof(S3)=FVAR(1)
 Fixed Sof: S2(0.6154) H14A(0.6154) H14B(0.6154) H14C(0.6154) H14D(0.3846)
 H14E(0.3846) H14F(0.3846) H16A(0.94915) H16B(0.94915) H16C(0.94915)
 H16D(0.05085) H16E(0.05085) H16F(0.05085) H15A(0.6154) H15B(0.6154)
 H15C(0.6154) H15D(0.3846) H15E(0.3846) H15F(0.3846) H17A(0.94915)
 H17B(0.94915) H17C(0.94915) H17D(0.05085) H17E(0.05085) H17F(0.05085)
 S2A(0.3846)
4.a Rotating group:
 N2(H2A,H2B)
4.b Ternary CH refined with riding coordinates:
 C4(H4)
4.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B)
4.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C10(H10), C12(H12)
4.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C14(H14D,H14E,H14F), C16(H16A,H16B,H16C), C16(H16D,H16E,
 H16F), C15(H15A,H15B,H15C), C15(H15D,H15E,H15F), C17(H17A,H17B,H17C), C17(H17D,
 H17E,H17F)
;
loop_
_space_group_symop_operation_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_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
S5 S 0.43401(9) 0.28860(5) 0.47856(7) 0.0486(2) Uani 1 1 d . . . . .
S1 S 0.76547(8) -0.05590(6) 0.34727(7) 0.0499(2) Uani 1 1 d . . . . .
S3 S 1.12785(11) 0.66439(7) 0.10082(8) 0.0698(4) Uani 0.949(3) 1 d . U P A 1
S2 S 0.98129(14) 0.13438(11) 0.10751(12) 0.0584(3) Uani 0.6154 1 d . . P B 1
C8 C 0.5438(3) 0.31566(19) 0.2940(2) 0.0376(5) Uani 1 1 d . . . . .
C7 C 0.6744(3) -0.1845(2) 0.3744(3) 0.0460(6) Uani 1 1 d . . . . .
H7A H 0.563734 -0.219448 0.308525 0.055 Uiso 1 1 calc R . . . .
H7B H 0.754819 -0.241124 0.375323 0.055 Uiso 1 1 calc R . . . .
C4 C 0.4894(3) 0.22227(19) 0.3448(2) 0.0370(5) Uani 1 1 d . . . . .
H4 H 0.381384 0.174514 0.282538 0.044 Uiso 1 1 calc R . . . .
C3 C 0.6240(3) 0.1418(2) 0.3712(2) 0.0373(5) Uani 1 1 d . . . . .
C2 C 0.5879(3) 0.0248(2) 0.3224(2) 0.0379(5) Uani 1 1 d . . . . .
C6 C 0.3564(4) 0.1557(2) 0.5072(3) 0.0509(6) Uani 1 1 d . . . . .
H6A H 0.247554 0.116333 0.441578 0.061 Uiso 1 1 calc R . . . .
H6B H 0.443230 0.103410 0.509866 0.061 Uiso 1 1 calc R . . . .
N2 N 0.4276(3) -0.03503(18) 0.2498(2) 0.0558(6) Uani 1 1 d . . . . .
H2A H 0.417242 -0.102996 0.261567 0.067 Uiso 1 1 d GR . . . .
H2B H 0.348384 0.002270 0.267350 0.067 Uiso 1 1 d GR . . . .
C9 C 0.6630(3) 0.4156(2) 0.3658(3) 0.0495(6) Uani 1 1 d . . . . .
H9 H 0.705546 0.429134 0.449882 0.059 Uiso 1 1 calc R . . . .
F1 F 0.7122(3) 0.55134(18) 0.1415(2) 0.0960(7) Uani 1 1 d . . . . .
C3' C 0.7951(3) 0.1965(2) 0.4552(3) 0.0485(6) Uani 1 1 d . . . . .
C13 C 0.4804(3) 0.2991(2) 0.1693(3) 0.0493(6) Uani 1 1 d . . . . .
H13 H 0.398489 0.233418 0.119469 0.059 Uiso 1 1 calc R . . . .
C11 C 0.6551(4) 0.4738(3) 0.1927(3) 0.0605(8) Uani 1 1 d . . . . .
O1 O 1.1013(2) 0.0625(2) 0.1670(2) 0.0871(8) Uani 1 1 d . . . . .
O2 O 1.2973(3) 0.72594(19) 0.1083(2) 0.0804(7) Uani 1 1 d . U . . .
C10 C 0.7199(4) 0.4954(2) 0.3153(3) 0.0577(8) Uani 1 1 d . . . . .
H10 H 0.800323 0.562025 0.364009 0.069 Uiso 1 1 calc R . . . .
C12 C 0.5363(4) 0.3780(3) 0.1173(3) 0.0627(8) Uani 1 1 d . . . . .
H12 H 0.494131 0.366190 0.033391 0.075 Uiso 1 1 calc R . . . .
C14 C 0.9837(5) 0.2586(3) 0.2196(4) 0.0950(13) Uani 1 1 d . . . . .
H14A H 0.956881 0.235447 0.283298 0.142 Uiso 0.6154 1 calc GR . P B 1
H14B H 0.897160 0.303268 0.184378 0.142 Uiso 0.6154 1 calc GR . P B 1
H14C H 1.098302 0.305325 0.252769 0.142 Uiso 0.6154 1 calc GR . P B 1
H14D H 1.085994 0.298219 0.288981 0.142 Uiso 0.3846 1 calc GR . P B 2
H14E H 0.880720 0.287337 0.230264 0.142 Uiso 0.3846 1 calc GR . P B 2
H14F H 0.995714 0.272597 0.147559 0.142 Uiso 0.3846 1 calc GR . P B 2
C16 C 1.0354(6) 0.7677(4) 0.1842(5) 0.1105(16) Uani 1 1 d . U . . .
H16A H 1.112558 0.793748 0.267791 0.166 Uiso 0.9491 1 calc GR . P A 1
H16B H 0.922927 0.732269 0.179403 0.166 Uiso 0.9491 1 calc GR . P A 1
H16C H 1.020391 0.833137 0.150708 0.166 Uiso 0.9491 1 calc GR . P A 1
H16D H 1.053914 0.849966 0.222709 0.166 Uiso 0.0508 1 calc GR . P A 2
H16E H 0.958695 0.727752 0.213038 0.166 Uiso 0.0508 1 calc GR . P A 2
H16F H 0.982451 0.753600 0.097639 0.166 Uiso 0.0508 1 calc GR . P A 2
C15 C 0.7648(3) 0.0644(3) 0.0729(3) 0.0788(10) Uani 1 1 d . . . . .
H15A H 0.740627 -0.007107 0.009651 0.118 Uiso 0.6154 1 calc GR . P B 1
H15B H 0.682015 0.114667 0.045950 0.118 Uiso 0.6154 1 calc GR . P B 1
H15C H 0.754403 0.047752 0.144311 0.118 Uiso 0.6154 1 calc GR . P B 1
H15D H 0.774996 0.098692 0.010834 0.118 Uiso 0.3846 1 calc GR . P B 2
H15E H 0.665845 0.087642 0.094175 0.118 Uiso 0.3846 1 calc GR . P B 2
H15F H 0.748002 -0.019064 0.043077 0.118 Uiso 0.3846 1 calc GR . P B 2
C17 C 1.1776(5) 0.5736(3) 0.2001(4) 0.0940(12) Uani 1 1 d . U . . .
H17A H 1.222724 0.507373 0.164814 0.141 Uiso 0.9491 1 calc GR . P A 1
H17B H 1.072541 0.547365 0.212475 0.141 Uiso 0.9491 1 calc GR . P A 1
H17C H 1.264461 0.616850 0.276870 0.141 Uiso 0.9491 1 calc GR . P A 1
H17D H 1.160360 0.530772 0.118189 0.141 Uiso 0.0508 1 calc GR . P A 2
H17E H 1.077258 0.551926 0.220007 0.141 Uiso 0.0508 1 calc GR . P A 2
H17F H 1.281476 0.555915 0.255073 0.141 Uiso 0.0508 1 calc GR . P A 2
N1 N 0.9259(3) 0.2494(2) 0.5227(3) 0.0758(9) Uani 1 1 d . . . . .
S2A S 0.9636(2) 0.11333(17) 0.20572(17) 0.0533(4) Uani 0.3846 1 d . . P B 2
S3A S 1.203(3) 0.7251(16) 0.213(2) 0.088(8) Uani 0.051(3) 1 d . U P 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'
F F 0.0171 0.0103 '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'
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'
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
_geom_angle_publ_flag
C6 S5 C4 98.74(12) . . ?
C2 S1 C7 102.82(10) . . ?
O2 S3 C16 106.57(17) . . ?
O2 S3 C17 107.61(17) . . ?
C16 S3 C17 98.2(2) . . ?
O1 S2 C14 107.86(18) . . ?
O1 S2 C15 106.55(18) . . ?
C14 S2 C15 98.7(2) . . ?
C9 C8 C4 123.0(2) . . ?
C13 C8 C4 119.0(2) . . ?
C13 C8 C9 117.9(2) . . ?
C6 C7 S1 111.46(18) 2_656 . ?
C8 C4 S5 109.96(15) . . ?
C8 C4 C3 113.09(18) . . ?
C3 C4 S5 112.13(16) . . ?
C2 C3 C4 123.58(18) . . ?
C2 C3 C3' 120.74(19) . . ?
C3' C3 C4 115.7(2) . . ?
C3 C2 S1 118.19(16) . . ?
N2 C2 S1 116.90(17) . . ?
N2 C2 C3 124.79(19) . . ?
C7 C6 S5 110.04(18) 2_656 . ?
C10 C9 C8 121.5(3) . . ?
N1 C3' C3 173.9(3) . . ?
C12 C13 C8 121.3(2) . . ?
C10 C11 F1 118.6(3) . . ?
C10 C11 C12 123.3(3) . . ?
C12 C11 F1 118.1(3) . . ?
C11 C10 C9 118.0(3) . . ?
C11 C12 C13 118.0(3) . . ?
O1 S2A C14 110.9(2) . . ?
O1 S2A C15 104.90(18) . . ?
C14 S2A C15 99.34(19) . . ?
O2 S3A C17 99.2(9) . . ?
C16 S3A O2 112.7(15) . . ?
C16 S3A C17 112.1(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S5 C4 1.834(3) . ?
S5 C6 1.821(3) . ?
S1 C7 1.808(3) . ?
S1 C2 1.771(2) . ?
S3 O2 1.484(2) . ?
S3 C16 1.769(4) . ?
S3 C17 1.773(4) . ?
S2 O1 1.466(2) . ?
S2 C14 1.750(4) . ?
S2 C15 1.769(3) . ?
C8 C4 1.503(3) . ?
C8 C9 1.386(3) . ?
C8 C13 1.384(4) . ?
C7 C6 1.499(4) 2_656 ?
C4 C3 1.509(3) . ?
C3 C2 1.352(3) . ?
C3 C3' 1.426(3) . ?
C2 N2 1.345(3) . ?
C9 C10 1.379(4) . ?
F1 C11 1.365(3) . ?
C3' N1 1.138(3) . ?
C13 C12 1.382(4) . ?
C11 C10 1.353(4) . ?
C11 C12 1.362(4) . ?
O1 S2A 1.462(3) . ?
O2 S3A 1.69(2) . ?
C14 S2A 1.695(4) . ?
C16 S3A 1.45(2) . ?
C15 S2A 1.806(3) . ?
C17 S3A 1.771(19) . ?
