#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:48:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180097 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/43/7054362.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_7054362
loop_
_publ_author_name
'Basu, Basudeb'
'Kundu, Samir'
_publ_section_title
;
 Unprecedented amidation of ‘transient’ aryl thioaldehydes
 by N,N-dimethylformamide under basic conditions
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3367
_journal_paper_doi               10.1039/C4NJ00480A
_journal_volume                  38
_journal_year                    2014
_chemical_formula_sum            'C9 H10 Cl N S'
_chemical_formula_weight         199.69
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.198(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1194(3)
_cell_length_b                   14.4115(4)
_cell_length_c                   7.3274(2)
_cell_measurement_temperature    296(2)
_cell_volume                     1026.18(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0950
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12072
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.46
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.522
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1418
_reflns_number_gt                1546
_reflns_number_total             2559
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7054192
_cod_data_source_file            c4nj00480a2.cif
_cod_data_source_block           smk-170
_cod_database_code               7054362
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 1.0648(2) 0.13846(14) 0.9550(3) 0.0750(6) Uani 1 1 d .
H1A H 1.0711 0.1714 1.0709 0.113 Uiso 1 1 calc R
H1B H 1.1113 0.1729 0.8792 0.113 Uiso 1 1 calc R
H1C H 1.1071 0.0786 0.9840 0.113 Uiso 1 1 calc R
C2 C 0.8954(2) 0.12255(14) 0.6441(3) 0.0675(5) Uani 1 1 d .
H2A H 0.8019 0.1043 0.5859 0.101 Uiso 1 1 calc R
H2B H 0.9566 0.0780 0.6138 0.101 Uiso 1 1 calc R
H2C H 0.9117 0.1825 0.5974 0.101 Uiso 1 1 calc R
C3 C 0.82325(18) 0.11726(10) 0.9392(3) 0.0522(5) Uani 1 1 d .
C4 C 0.67709(18) 0.11684(12) 0.8229(2) 0.0507(4) Uani 1 1 d .
C5 C 0.61991(19) 0.19443(14) 0.7181(3) 0.0670(5) Uani 1 1 d .
H5 H 0.6746 0.2462 0.7175 0.080 Uiso 1 1 calc R
C6 C 0.4834(2) 0.19578(15) 0.6150(3) 0.0714(6) Uani 1 1 d .
H6 H 0.4463 0.2480 0.5448 0.086 Uiso 1 1 calc R
C7 C 0.4023(2) 0.11919(14) 0.6167(3) 0.0631(5) Uani 1 1 d .
C8 C 0.45600(18) 0.04164(14) 0.7186(3) 0.0713(6) Uani 1 1 d .
H8 H 0.4011 -0.0102 0.7178 0.086 Uiso 1 1 calc R
C9 C 0.5926(2) 0.04131(13) 0.8223(3) 0.0654(5) Uani 1 1 d .
H9 H 0.6287 -0.0109 0.8934 0.078 Uiso 1 1 calc R
N1 N 0.91987(15) 0.12689(9) 0.8493(2) 0.0547(4) Uani 1 1 d .
S1 S 0.85795(5) 0.10716(4) 1.17517(7) 0.0680(2) Uani 1 1 d .
Cl1 Cl 0.23012(6) 0.12029(4) 0.48319(10) 0.0917(3) 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'
Cl Cl 0.1484 0.1585 '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
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 H2A 109.5
N1 C2 H2B 109.5
H2A C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
N1 C3 C4 117.92(16)
N1 C3 S1 123.36(14)
C4 C3 S1 118.72(13)
C9 C4 C5 118.03(17)
C9 C4 C3 121.36(16)
C5 C4 C3 120.55(15)
C6 C5 C4 120.96(18)
C6 C5 H5 119.5
C4 C5 H5 119.5
C5 C6 C7 119.53(18)
C5 C6 H6 120.2
C7 C6 H6 120.2
C8 C7 C6 120.76(18)
C8 C7 Cl1 119.72(15)
C6 C7 Cl1 119.50(15)
C7 C8 C9 119.19(17)
C7 C8 H8 120.4
C9 C8 H8 120.4
C8 C9 C4 121.52(17)
C8 C9 H9 119.2
C4 C9 H9 119.2
C3 N1 C2 124.78(15)
C3 N1 C1 121.11(16)
C2 N1 C1 114.05(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.464(2)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 N1 1.455(2)
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
C3 N1 1.330(2)
C3 C4 1.487(2)
C3 S1 1.6722(18)
C4 C9 1.384(2)
C4 C5 1.388(2)
C5 C6 1.377(2)
C5 H5 0.9300
C6 C7 1.378(3)
C6 H6 0.9300
C7 C8 1.369(3)
C7 Cl1 1.744(2)
C8 C9 1.379(2)
C8 H8 0.9300
C9 H9 0.9300
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 C3 C4 C9 119.89(19)
S1 C3 C4 C9 -60.9(2)
N1 C3 C4 C5 -63.0(2)
S1 C3 C4 C5 116.16(16)
C9 C4 C5 C6 -0.6(3)
C3 C4 C5 C6 -177.84(18)
C4 C5 C6 C7 0.3(3)
C5 C6 C7 C8 -0.4(3)
C5 C6 C7 Cl1 -179.02(15)
C6 C7 C8 C9 0.9(3)
Cl1 C7 C8 C9 179.45(15)
C7 C8 C9 C4 -1.2(3)
C5 C4 C9 C8 1.1(3)
C3 C4 C9 C8 178.26(17)
C4 C3 N1 C2 -10.1(2)
S1 C3 N1 C2 170.75(13)
C4 C3 N1 C1 173.03(14)
S1 C3 N1 C1 -6.1(2)
