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_7242925
_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 Cl2 N4 S4, 6(C2 H6 O S)'
_chemical_formula_sum            'C36 H58 Cl2 N4 O6 S10'
_chemical_formula_weight         1034.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.600(2)
_cell_length_b                   9.7722(10)
_cell_length_c                   28.091(6)
_cell_measurement_reflns_used    1892
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9470
_cell_measurement_theta_min      2.4800
_cell_volume                     5105.9(13)
_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    'ShelXT (Sheldrick, 2015)'
_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  -18.25   23.00   0.7500   46.0600
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000   60.0000 55

  2 omega    2.00   52.25   0.7500   46.0600
omega____ theta____ kappa____ phi______ frames
    -       16.9480   57.0000 -120.0000 67

  3 omega  -40.00   30.50   0.7500   46.0600
omega____ theta____ kappa____ phi______ frames
    -       16.9480  -57.0000  -90.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0193217000
_diffrn_orient_matrix_UB_12      -0.0206468000
_diffrn_orient_matrix_UB_13      0.0205503000
_diffrn_orient_matrix_UB_21      -0.0326632000
_diffrn_orient_matrix_UB_22      -0.0200831000
_diffrn_orient_matrix_UB_23      0.0110984000
_diffrn_orient_matrix_UB_31      0.0038536000
_diffrn_orient_matrix_UB_32      -0.0665871000
_diffrn_orient_matrix_UB_33      -0.0096524000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1149
_diffrn_reflns_av_unetI/netI     0.1509
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            15833
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.390
_diffrn_reflns_theta_min         2.190
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53548
_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    1.346
_exptl_crystal_description       plank
_exptl_crystal_F_000             2176
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5993
_refine_ls_number_restraints     145
_refine_ls_restrained_S_all      0.908
_refine_ls_R_factor_all          0.2347
_refine_ls_R_factor_gt           0.0998
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1129P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2187
_refine_ls_wR_factor_ref         0.2941
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1864
_reflns_number_total             5993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra02616j2.cif
_cod_data_source_block           ans-763
_cod_database_code               7242925
_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. Restrained distances
 O2-S3 \\sim O2-S3A
 with sigma of 0.02
3. Rigid bond restraints
 S2, O1, C14, C15, S2A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 S3, O2, S3A, C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
S2A \\sim S2 \\sim O1 \\sim C14 \\sim C15: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
O2: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
S3 \\sim O2 \\sim S3A \\sim C16 \\sim C17: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 S2A, S2, O1, C14, C15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S3A, O2, S3, C16, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: S2(0.91555) S4(0.5994) H19A(0.5994) H19B(0.5994) H19C(0.5994)
 H19D(0.4006) H19E(0.4006) H19F(0.4006) H14A(0.91555) H14B(0.91555)
 H14C(0.91555) H14D(0.08445) H14E(0.08445) H14F(0.08445) H18A(0.5994)
 H18B(0.5994) H18C(0.5994) H18D(0.4006) H18E(0.4006) H18F(0.4006) H15A(0.91555)
 H15B(0.91555) H15C(0.91555) H15D(0.08445) H15E(0.08445) H15F(0.08445)
 S4A(0.4006) S2A(0.08445) S3(0.53652) S3A(0.46348) H16A(0.53652) H16B(0.53652)
 H16C(0.53652) H16D(0.46348) H16E(0.46348) H16F(0.46348) H17A(0.53652)
 H17B(0.53652) H17C(0.53652) H17D(0.46348) H17E(0.46348) H17F(0.46348)
7.a Ternary CH refined with riding coordinates:
 C4(H4)
7.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B)
7.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C9(H9), C13(H13), C10(H10)
7.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
7.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C19(H19D,H19E,H19F), C14(H14A,H14B,H14C), C14(H14D,H14E,
 H14F), C18(H18A,H18B,H18C), C18(H18D,H18E,H18F), C15(H15A,H15B,H15C), C15(H15D,
 H15E,H15F), C16(H16A,H16B,H16C), C16(H16D,H16E,H16F), C17(H17A,H17B,H17C),
 C17(H17D,H17E,H17F)
;