#------------------------------------------------------------------------------
#$Date: 2016-10-06 09:46:12 +0300 (Thu, 06 Oct 2016) $
#$Revision: 186978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/67/7226722.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_7226722
loop_
_publ_author_name
'Opris, Dorina'
'Caspari, Philip'
'Nueesch, Frank'
'Neels, Antonia'
_publ_section_title
;
 Mild synthesis of mercaptonitriles from vinyl nitriles and their
 cyclization reactions
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA21948A
_journal_year                    2016
_chemical_formula_moiety         'C16 H24 N4 S4'
_chemical_formula_sum            'C16 H24 N4 S4'
_chemical_formula_weight         400.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-09-28 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.007(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7678(7)
_cell_length_b                   8.9291(5)
_cell_length_c                   12.0069(8)
_cell_measurement_reflns_used    18427
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.56
_cell_measurement_theta_min      1.79
_cell_volume                     990.12(12)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1111
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13148
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.191
_diffrn_reflns_theta_min         2.346
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.486
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         2679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0953P)²+0.2587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1653
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2334
_reflns_number_total             2679
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ra21948a2.cif
_cod_data_source_block           Compound-17
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               7226722
_shelx_shelxl_version_number     2014/7
_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. 
;
_shelx_estimated_absorpt_t_min   0.829
_shelx_estimated_absorpt_t_max   0.909
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C1 C 0.8248(2) 0.6571(2) 0.08414(18) 0.0461(4) Uani 1 1 d . .
H1A H 0.7587 0.7246 0.0289 0.055 Uiso 1 1 calc R U
H1B H 0.9201 0.6704 0.0770 0.055 Uiso 1 1 calc R U
C2 C 0.7759(3) 0.4979(2) 0.0529(2) 0.0508(5) Uani 1 1 d . .
H2A H 0.6765 0.4877 0.0516 0.061 Uiso 1 1 calc R U
H2B H 0.8352 0.4315 0.1134 0.061 Uiso 1 1 calc R U
C3 C 0.6473(2) 0.5559(2) -0.18786(19) 0.0457(4) Uani 1 1 d . .
H3A H 0.5609 0.5532 -0.1648 0.055 Uiso 1 1 calc R U
H3B H 0.6801 0.6589 -0.1839 0.055 Uiso 1 1 calc R U
C4 C 0.6124(2) 0.4973(3) -0.31331(19) 0.0537(5) Uani 1 1 d . .
H4A H 0.7018 0.4872 -0.3312 0.064 Uiso 1 1 calc R U
H4B H 0.5524 0.5702 -0.3674 0.064 Uiso 1 1 calc R U
C5 C 0.4661(2) 0.6539(3) 0.33340(17) 0.0477(4) Uani 1 1 d . .
H5B H 0.4075 0.7267 0.2783 0.057 Uiso 1 1 calc R U
H5A H 0.4776 0.6888 0.4125 0.057 Uiso 1 1 calc R U
C6 C 0.6152(2) 0.6437(2) 0.31760(16) 0.0415(4) Uani 1 1 d . .
C7 C 0.6477(2) 0.6992(2) 0.22379(17) 0.0409(4) Uani 1 1 d . .
C8 C 0.7262(2) 0.5710(2) 0.40980(16) 0.0417(4) Uani 1 1 d . .
N1 N 0.5492(2) 0.7548(2) 0.12504(17) 0.0489(4) Uani 1 1 d . .
H1N H 0.462(3) 0.758(3) 0.125(3) 0.061(8) Uiso 1 1 d . .
H2N H 0.584(3) 0.817(4) 0.092(3) 0.067(8) Uiso 1 1 d . .
N2 N 0.8074(2) 0.5108(2) 0.48791(15) 0.0489(4) Uani 1 1 d . .
S1 S 0.83147(5) 0.70500(6) 0.23269(4) 0.04787(19) Uani 1 1 d . .
S2 S 0.78742(6) 0.44079(6) -0.08845(5) 0.0510(2) Uani 1 1 d . .
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'
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
C2 C1 S1 111.96(14) . .
C2 C1 H1A 109.2 . .
S1 C1 H1A 109.2 . .
C2 C1 H1B 109.2 . .
S1 C1 H1B 109.2 . .
H1A C1 H1B 107.9 . .
C1 C2 S2 112.80(15) . .
C1 C2 H2A 109.0 . .
S2 C2 H2A 109.0 . .
C1 C2 H2B 109.0 . .
S2 C2 H2B 109.0 . .
H2A C2 H2B 107.8 . .
C4 C3 S2 109.49(15) . .
C4 C3 H3A 109.8 . .
S2 C3 H3A 109.8 . .
C4 C3 H3B 109.8 . .
S2 C3 H3B 109.8 . .
H3A C3 H3B 108.2 . .
C3 C4 C5 113.41(17) . 3_665
C3 C4 H4A 108.9 . .
C5 C4 H4A 108.9 3_665 .
C3 C4 H4B 108.9 . .
C5 C4 H4B 108.9 3_665 .
H4A C4 H4B 107.7 . .
C6 C5 C4 112.04(17) . 3_665
C6 C5 H5B 109.2 . .
C4 C5 H5B 109.2 3_665 .
C6 C5 H5A 109.2 . .
C4 C5 H5A 109.2 3_665 .
H5B C5 H5A 107.9 . .
C7 C6 C8 119.02(18) . .
C7 C6 C5 124.66(17) . .
C8 C6 C5 116.32(17) . .
N1 C7 C6 124.65(19) . .
N1 C7 S1 117.42(16) . .
C6 C7 S1 117.89(15) . .
N2 C8 C6 174.7(2) . .
C7 N1 H1N 116(2) . .
C7 N1 H2N 113(2) . .
H1N N1 H2N 124(3) . .
C7 S1 C1 102.90(9) . .
C2 S2 C3 101.14(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.508(3) .
C1 S1 1.814(2) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 S2 1.810(2) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.525(3) .
C3 S2 1.8141(19) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.533(3) 3_665
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.532(3) .
C5 C4 1.533(3) 3_665
C5 H5B 0.9700 .
C5 H5A 0.9700 .
C6 C7 1.359(3) .
C6 C8 1.429(3) .
C7 N1 1.355(3) .
C7 S1 1.764(2) .
C8 N2 1.146(3) .
N1 H1N 0.85(3) .
N1 H2N 0.82(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1A N2 0.97 2.63 3.415(3) 138.5 2_655
C1 H1B S2 0.97 2.99 3.872(2) 152.5 3_765
C4 H4A N2 0.97 2.70 3.508(3) 141.2 1_554
N1 H1N S2 0.85(3) 2.93(3) 3.621(2) 140(2) 3_665
N1 H2N N2 0.82(3) 2.38(4) 3.204(3) 174(3) 2_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
S1 C1 C2 S2 -173.58(11) . .
S2 C3 C4 C5 70.0(2) . 3_665
C4 C5 C6 C7 106.5(2) 3_665 .
C4 C5 C6 C8 -73.9(2) 3_665 .
C8 C6 C7 N1 172.08(18) . .
C5 C6 C7 N1 -8.3(3) . .
C8 C6 C7 S1 -10.1(2) . .
C5 C6 C7 S1 169.47(14) . .
N1 C7 S1 C1 -39.80(17) . .
C6 C7 S1 C1 142.22(15) . .
C2 C1 S1 C7 -66.54(17) . .
C1 C2 S2 C3 -68.23(18) . .
C4 C3 S2 C2 -165.68(14) . .
