Metal-free multicomponent synthesis of novel macrocyclic tetrathiadienes with cyano and amino groups
Akhmadiev, Nail S.; Mescheryakova, Ekaterina S.; Akhmetova, Vnira R.; Ibragimov, Askhat G.; RSC Advances 11 (2021) 18768–18775; doi:10.1039/D1RA02616J

data_7242923
_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
;
  1 omega    7.00   43.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480  -19.0000   30.0000 36

  2 omega   55.00   87.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480   19.0000  -60.0000 32

  3 omega    4.00   74.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480   38.0000 -150.0000 70

  4 omega   -7.00   21.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480   19.0000  -60.0000 28

  5 omega  -54.00   -6.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480  -19.0000   30.0000 48

  6 omega  -23.00   20.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000   30.0000 43

  7 omega  -20.00   49.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480  -99.0000    0.0000 69

  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       '\w 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/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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
_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)
;