#------------------------------------------------------------------------------
#$Date: 2016-10-06 09:46:12 +0300 (Thu, 06 Oct 2016) $
#$Revision: 186978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/67/7226723.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_7226723
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         'C6 H8 N2 S'
_chemical_formula_sum            'C6 H8 N2 S'
_chemical_formula_weight         140.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_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                 133.640(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.7040(8)
_cell_length_b                   7.7645(4)
_cell_length_c                   15.7661(9)
_cell_measurement_reflns_used    10685
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.47
_cell_measurement_theta_min      2.82
_cell_volume                     1391.24(15)
_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      173(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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  0.0574
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10854
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.189
_diffrn_reflns_theta_min         2.816
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       rod
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0301
_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)+(0.0548P)²+0.3965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1656
_reflns_number_total             1867
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ra21948a2.cif
_cod_data_source_block           Compound-8
_cod_original_cell_volume        1391.23(14)
_cod_database_code               7226723
_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   0.836
_shelx_estimated_absorpt_t_max   0.929
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C -0.01554(10) 0.52543(15) 0.11414(10) 0.0213(2) Uani 1 1 d
C2 C -0.11421(11) 0.43994(15) 0.02091(10) 0.0223(2) Uani 1 1 d
C3 C -0.12181(12) 0.25081(16) -0.00694(12) 0.0281(3) Uani 1 1 d
H3A H -0.1279(15) 0.238(2) -0.0729(15) 0.032(4) Uiso 1 1 d
H3B H -0.1933(17) 0.206(2) -0.0320(16) 0.042(5) Uiso 1 1 d
C4 C -0.01802(13) 0.14615(16) 0.09721(13) 0.0318(3) Uani 1 1 d
H4A H -0.0213(15) 0.137(2) 0.1539(15) 0.032(4) Uiso 1 1 d
H4B H -0.0255(16) 0.027(2) 0.0694(15) 0.039(4) Uiso 1 1 d
C5 C 0.09793(12) 0.22445(17) 0.14970(12) 0.0308(3) Uani 1 1 d
H5A H 0.1019(16) 0.241(2) 0.0900(16) 0.038(4) Uiso 1 1 d
H5B H 0.1627(18) 0.156(3) 0.2108(17) 0.046(5) Uiso 1 1 d
C6 C -0.21883(11) 0.53751(16) -0.05875(11) 0.0248(3) Uani 1 1 d
N1 N -0.01359(10) 0.69715(14) 0.13548(10) 0.0273(2) Uani 1 1 d
H1N H 0.0526(16) 0.736(2) 0.2049(15) 0.032(4) Uiso 1 1 d
H2N H -0.0792(17) 0.739(2) 0.1110(15) 0.036(4) Uiso 1 1 d
N2 N -0.30490(10) 0.61495(16) -0.12540(11) 0.0347(3) Uani 1 1 d
S1 S 0.12310(3) 0.43027(4) 0.21769(3) 0.02845(13) 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
C2 C1 N1 123.69(11)
C2 C1 S1 123.95(9)
N1 C1 S1 112.35(9)
C1 C2 C6 117.12(10)
C1 C2 C3 126.05(11)
C6 C2 C3 116.82(11)
C2 C3 C4 113.17(11)
C2 C3 H3A 109.7(10)
C4 C3 H3A 109.7(10)
C2 C3 H3B 108.0(11)
C4 C3 H3B 109.0(11)
H3A C3 H3B 107.1(15)
C5 C4 C3 111.33(11)
C5 C4 H4A 110.4(11)
C3 C4 H4A 110.5(11)
C5 C4 H4B 110.3(11)
C3 C4 H4B 107.9(10)
H4A C4 H4B 106.3(14)
C4 C5 S1 111.54(10)
C4 C5 H5A 112.0(11)
S1 C5 H5A 108.2(10)
C4 C5 H5B 112.1(12)
S1 C5 H5B 104.5(12)
H5A C5 H5B 108.2(15)
N2 C6 C2 178.70(14)
C1 N1 H1N 115.9(11)
C1 N1 H2N 115.6(12)
H1N N1 H2N 115.9(16)
C1 S1 C5 101.43(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3632(16)
C1 N1 1.3703(15)
C1 S1 1.7451(12)
C2 C6 1.4151(16)
C2 C3 1.5137(17)
C3 C4 1.5229(19)
C3 H3A 0.983(17)
C3 H3B 0.96(2)
C4 C5 1.513(2)
C4 H4A 0.933(17)
C4 H4B 0.995(19)
C5 S1 1.8095(14)
C5 H5A 0.994(18)
C5 H5B 0.94(2)
C6 N2 1.1542(18)
N1 H1N 0.893(18)
N1 H2N 0.875(19)
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
N1 H1N N2 0.893(18) 2.290(18) 3.1668(16) 166.8(15) 8_566
N1 H2N N2 0.875(19) 2.286(19) 3.1069(16) 156.3(15) 7_465
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
N1 C1 C2 C6 1.64(18)
S1 C1 C2 C6 -176.73(9)
N1 C1 C2 C3 -179.81(12)
S1 C1 C2 C3 1.81(19)
C1 C2 C3 C4 17.57(19)
C6 C2 C3 C4 -163.88(12)
C2 C3 C4 C5 -52.98(16)
C3 C4 C5 S1 67.45(14)
C2 C1 S1 C5 10.10(12)
N1 C1 S1 C5 -168.44(9)
C4 C5 S1 C1 -42.91(11)
