#------------------------------------------------------------------------------
#$Date: 2015-08-13 05:17:52 +0300 (Thu, 13 Aug 2015) $
#$Revision: 153380 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/09/2240993.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2240993
loop_
_publ_author_name
'Ameram, Nadiah'
'Adam, Farook'
_publ_section_title
;
 Crystal structure of
 2-methyl-N-{[2-(pyridin-2-yl)ethyl]carbamothioyl}benzamide
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o636
_journal_paper_doi               10.1107/S2056989015013559
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C16 H17 N3 O S'
_chemical_formula_moiety         'C16 H17 N3 O S'
_chemical_formula_sum            'C16 H17 N3 O S'
_chemical_formula_weight         299.38
_chemical_name_systematic
;
2-Methyl-N-{[2-(pyridin-2-yl)ethyl]carbamothioyl}benzamide
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                86.1868(13)
_cell_angle_beta                 83.3739(13)
_cell_angle_gamma                73.8746(13)
_cell_formula_units_Z            2
_cell_length_a                   8.5434(4)
_cell_length_b                   8.7477(4)
_cell_length_c                   11.0530(5)
_cell_measurement_reflns_used    8347
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.43
_cell_volume                     787.73(6)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30520
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.292
_diffrn_reflns_theta_min         1.856
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.8669
_exptl_absorpt_correction_T_min  0.6700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.532
_exptl_crystal_size_mid          0.424
_exptl_crystal_size_min          0.224
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0447
_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)+(0.0515P)²+0.2342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1287
_reflns_number_gt                3412
_reflns_number_total             4698
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5173sup1.cf
_cod_data_source_block           I
_cod_database_code               2240993
_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   0.898
_shelx_estimated_absorpt_t_max   0.955
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
S S1 0.29858(5) 1.05179(5) -0.14484(4) 0.05473(14) Uani d 1
O O1 0.46415(15) 0.62159(12) 0.10945(10) 0.0552(3) Uani d 1
N N1 0.32417(14) 0.87622(13) 0.05803(10) 0.0367(2) Uani d 1
N N2 0.47718(15) 0.75403(15) -0.11337(11) 0.0408(3) Uani d 1
N N3 0.87338(16) 0.81820(15) -0.15598(13) 0.0499(3) Uani d 1
C C1 0.3515(2) 0.72438(18) 0.36636(14) 0.0482(3) Uani d 1
C C2 0.2522(3) 0.7379(2) 0.47681(15) 0.0654(5) Uani d 1
H H2A 0.3012 0.7083 0.5488 0.079 Uiso calc 1
C C3 0.0847(3) 0.7934(3) 0.48282(18) 0.0731(6) Uani d 1
H H3A 0.0226 0.7999 0.5581 0.088 Uiso calc 1
C C4 0.0088(2) 0.8393(2) 0.37890(18) 0.0638(5) Uani d 1
H H4A -0.1046 0.8769 0.3828 0.077 Uiso calc 1
C C5 0.10295(19) 0.82906(18) 0.26820(15) 0.0478(3) Uani d 1
H H5A 0.0522 0.8619 0.1972 0.057 Uiso calc 1
C C6 0.27224(18) 0.77065(15) 0.26075(12) 0.0392(3) Uani d 1
C C7 0.36489(17) 0.74777(16) 0.13728(12) 0.0384(3) Uani d 1
C C8 0.37507(16) 0.88350(16) -0.06595(12) 0.0359(3) Uani d 1
C C9 0.5275(2) 0.73791(19) -0.24280(13) 0.0462(3) Uani d 1
H H9A 0.4348 0.7906 -0.2875 0.055 Uiso calc 1
H H9B 0.5589 0.6259 -0.2610 0.055 Uiso calc 1
C C10 0.6698(2) 0.80764(19) -0.28709(14) 0.0487(3) Uani d 1
H H10A 0.6926 0.7974 -0.3746 0.058 Uiso calc 1
H H10B 0.6371 0.9203 -0.2709 0.058 Uiso calc 1
C C11 0.82339(18) 0.73009(17) -0.22889(14) 0.0445(3) Uani d 1
C C12 0.9112(2) 0.5738(2) -0.2508(2) 0.0661(5) Uani d 1
H H12A 0.8745 0.5138 -0.3019 0.079 Uiso calc 1
C C13 1.0517(3) 0.5084(2) -0.1970(3) 0.0805(7) Uani d 1
H H13A 1.1105 0.4032 -0.2102 0.097 Uiso calc 1
C C14 1.1056(2) 0.5992(3) -0.1232(2) 0.0779(6) Uani d 1
H H14A 1.2021 0.5582 -0.0867 0.093 Uiso calc 1
C C15 1.0123(2) 0.7523(2) -0.1053(2) 0.0676(5) Uani d 1
H H15A 1.0477 0.8142 -0.0549 0.081 Uiso calc 1
C C16 0.5335(2) 0.6686(3) 0.36477(18) 0.0661(5) Uani d 1
H H16A 0.5808 0.7494 0.3264 0.099 Uiso calc 1
H H16B 0.5743 0.5728 0.3200 0.099 Uiso calc 1
H H16C 0.5624 0.6477 0.4468 0.099 Uiso calc 1
H H1N2 0.508(2) 0.676(2) -0.0647(16) 0.049(5) Uiso d 1
H H1N1 0.265(2) 0.967(2) 0.0876(16) 0.049(5) Uiso d 1
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'
O O 0.0106 0.0060 '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
C7 N1 C8 127.33(12)
C7 N1 H1N1 118.0(12)
C8 N1 H1N1 114.5(12)
C8 N2 C9 123.54(13)
C8 N2 H1N2 116.3(12)
C9 N2 H1N2 120.0(12)
C11 N3 C15 118.03(15)
C2 C1 C6 116.77(16)
C2 C1 C16 120.27(16)
C6 C1 C16 122.91(15)
C3 C2 C1 122.25(17)
C3 C2 H2A 118.9
C1 C2 H2A 118.9
C4 C3 C2 120.40(17)
C4 C3 H3A 119.8
C2 C3 H3A 119.8
C3 C4 C5 118.99(18)
C3 C4 H4A 120.5
C5 C4 H4A 120.5
C4 C5 C6 121.16(16)
C4 C5 H5A 119.4
C6 C5 H5A 119.4
C5 C6 C1 120.41(14)
C5 C6 C7 118.19(13)
C1 C6 C7 121.25(13)
O1 C7 N1 123.59(13)
O1 C7 C6 121.89(12)
N1 C7 C6 114.47(11)
N2 C8 N1 117.23(12)
N2 C8 S1 124.66(11)
N1 C8 S1 118.08(10)
N2 C9 C10 113.56(12)
N2 C9 H9A 108.9
C10 C9 H9A 108.9
N2 C9 H9B 108.9
C10 C9 H9B 108.9
H9A C9 H9B 107.7
C11 C10 C9 113.91(13)
C11 C10 H10A 108.8
C9 C10 H10A 108.8
C11 C10 H10B 108.8
C9 C10 H10B 108.8
H10A C10 H10B 107.7
N3 C11 C12 121.26(16)
N3 C11 C10 117.10(13)
C12 C11 C10 121.64(16)
C13 C12 C11 119.68(19)
C13 C12 H12A 120.2
C11 C12 H12A 120.2
C12 C13 C14 119.45(18)
C12 C13 H13A 120.3
C14 C13 H13A 120.3
C15 C14 C13 117.6(2)
C15 C14 H14A 121.2
C13 C14 H14A 121.2
N3 C15 C14 123.9(2)
N3 C15 H15A 118.0
C14 C15 H15A 118.0
C1 C16 H16A 109.5
C1 C16 H16B 109.5
H16A C16 H16B 109.5
C1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.6675(13)
O1 C7 1.2236(16)
N1 C7 1.3686(17)
N1 C8 1.3919(17)
N1 H1N1 0.874(18)
N2 C8 1.3203(18)
N2 C9 1.4499(18)
N2 H1N2 0.841(19)
N3 C11 1.331(2)
N3 C15 1.336(2)
C1 C2 1.396(2)
C1 C6 1.397(2)
C1 C16 1.494(3)
C2 C3 1.372(3)
C2 H2A 0.9300
C3 C4 1.366(3)
C3 H3A 0.9300
C4 C5 1.378(2)
C4 H4A 0.9300
C5 C6 1.388(2)
C5 H5A 0.9300
C6 C7 1.4926(19)
C9 C10 1.525(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.496(2)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.387(2)
C12 C13 1.364(3)
C12 H12A 0.9300
C13 C14 1.372(3)
C13 H13A 0.9300
C14 C15 1.369(3)
C14 H14A 0.9300
C15 H15A 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H1N2 O1 . 0.842(17) 1.971(18) 2.6550(16) 137.8(16)
N1 H1N1 N3 2_675 0.875(17) 2.061(17) 2.9366(17) 180(3)
C16 H16A S1 2_675 0.96 2.86 3.782(2) 162
C12 H12A Cg2 2_665 0.93 2.92 3.7724(19) 153
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
C6 C1 C2 C3 0.1(3)
C16 C1 C2 C3 177.89(19)
C1 C2 C3 C4 -0.6(3)
C2 C3 C4 C5 0.0(3)
C3 C4 C5 C6 1.1(3)
C4 C5 C6 C1 -1.6(2)
C4 C5 C6 C7 174.02(15)
C2 C1 C6 C5 0.9(2)
C16 C1 C6 C5 -176.76(16)
C2 C1 C6 C7 -174.53(14)
C16 C1 C6 C7 7.8(2)
C8 N1 C7 O1 5.5(2)
C8 N1 C7 C6 -171.85(12)
C5 C6 C7 O1 -128.16(16)
C1 C6 C7 O1 47.4(2)
C5 C6 C7 N1 49.22(18)
C1 C6 C7 N1 -135.22(14)
C9 N2 C8 N1 173.37(12)
C9 N2 C8 S1 -4.5(2)
C7 N1 C8 N2 -1.7(2)
C7 N1 C8 S1 176.26(11)
C8 N2 C9 C10 84.03(18)
N2 C9 C10 C11 61.39(18)
C15 N3 C11 C12 0.8(2)
C15 N3 C11 C10 -178.50(15)
C9 C10 C11 N3 -113.16(15)
C9 C10 C11 C12 67.54(19)
N3 C11 C12 C13 -0.1(3)
C10 C11 C12 C13 179.20(17)
C11 C12 C13 C14 -1.0(3)
C12 C13 C14 C15 1.2(3)
C11 N3 C15 C14 -0.5(3)
C13 C14 C15 N3 -0.5(4)

_cod_database_fobs_code 2240993
