#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/41/2014197.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_2014197
loop_
_publ_author_name
'Jacek Zaleski'
'Grzegorz Spaleniak'
'Kyzioł, Janusz B.'
_publ_section_title
;
 N-(3H-Thiazol-2-ylidene)nitramine and
 N-methyl-N-(thiazol-2-yl)nitramine
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o627
_journal_page_last               o629
_journal_paper_doi               10.1107/S0108270104001428
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C3 H3 N3 O2 S'
_chemical_formula_moiety         'C3 H3 N3 O2 S'
_chemical_formula_sum            'C3 H3 N3 O2 S'
_chemical_formula_weight         145.14
_chemical_name_systematic        ?
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/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                 114.57(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.737(3)
_cell_length_b                   3.7270(10)
_cell_length_c                   16.617(2)
_cell_measurement_reflns_used    2459
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.5
_cell_volume                     1055.3(4)
_computing_cell_refinement       'CrysAlis RED'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       ω
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7430
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         29.7
_diffrn_reflns_theta_min         3.4
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.385
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0449P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                1915
_reflns_number_total             2740
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na1637.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               2014197
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 0.30727(3) 0.99960(13) 0.45518(3) 0.01361(13) Uani d . 1 . . S
C2 0.39426(11) 0.7904(5) 0.47205(12) 0.0126(4) Uani d . 1 . . C
N3 0.43519(9) 0.7149(4) 0.55744(10) 0.0139(3) Uani d . 1 . . N
H3 0.4798 0.6075 0.5770 0.017 Uiso calc R 1 . . H
C4 0.40037(12) 0.8226(5) 0.61216(13) 0.0171(4) Uani d . 1 . . C
H4 0.4226 0.7880 0.6731 0.021 Uiso calc R 1 . . H
C5 0.33115(11) 0.9822(5) 0.56756(13) 0.0160(4) Uani d . 1 . . C
H5 0.2996 1.0729 0.5937 0.019 Uiso calc R 1 . . H
N6 0.42570(9) 0.6901(4) 0.41530(10) 0.0141(3) Uani d . 1 . . N
N7 0.38360(9) 0.7706(4) 0.32978(11) 0.0166(4) Uani d . 1 . . N
O8 0.31882(8) 0.9266(4) 0.30423(9) 0.0193(3) Uani d . 1 . . O
O9 0.41379(9) 0.6832(4) 0.27911(9) 0.0241(4) Uani d . 1 . . O
S1' 0.18949(3) 0.49066(13) 0.15011(3) 0.01294(13) Uani d . 1 . . S
C2' 0.10362(10) 0.2892(5) 0.07853(12) 0.0114(4) Uani d . 1 . . C
N3' 0.06265(9) 0.1717(4) 0.12250(10) 0.0124(3) Uani d . 1 . . N
H3' 0.0184 0.0631 0.0967 0.015 Uiso calc R 1 . . H
C4' 0.09642(11) 0.2372(5) 0.21211(13) 0.0151(4) Uani d . 1 . . C
H4' 0.0741 0.1696 0.2504 0.018 Uiso calc R 1 . . H
C5' 0.16518(11) 0.4094(5) 0.23794(13) 0.0155(4) Uani d . 1 . . C
H5' 0.1960 0.4769 0.2960 0.019 Uiso calc R 1 . . H
N6' 0.07359(9) 0.2316(4) -0.00929(10) 0.0130(3) Uani d . 1 . . N
N7' 0.11444(9) 0.3667(4) -0.05252(11) 0.0147(3) Uani d . 1 . . N
O8' 0.17677(8) 0.5354(4) -0.01257(9) 0.0179(3) Uani d . 1 . . O
O9' 0.08580(8) 0.3145(4) -0.13329(9) 0.0224(3) Uani d . 1 . . O
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
_geom_angle_publ_flag
C2 S1 C5 90.28(9) y
N3 C2 N6 117.28(17) y
N3 C2 S1 110.84(14) y
N6 C2 S1 131.88(15) y
C2 N3 C4 114.80(16) y
C2 N3 H3 122.6 ?
C4 N3 H3 122.6 ?
C5 C4 N3 112.30(18) ?
C5 C4 H4 123.8 ?
N3 C4 H4 123.8 ?
C4 C5 S1 111.77(15) ?
C4 C5 H5 124.1 ?
S1 C5 H5 124.1 ?
N7 N6 C2 116.17(15) y
O9 N7 O8 123.05(16) y
O9 N7 N6 115.34(16) y
O8 N7 N6 121.61(16) y
C2' S1' C5' 90.47(9) y
N3' C2' N6' 117.72(16) y
N3' C2' S1' 110.44(14) y
N6' C2' S1' 131.84(14) y
C2' N3' C4' 115.08(16) y
C2' N3' H3' 122.5 ?
C4' N3' H3' 122.5 ?
C5' C4' N3' 112.32(17) ?
C5' C4' H4' 123.8 ?
N3' C4' H4' 123.8 ?
C4' C5' S1' 111.69(15) ?
C4' C5' H5' 124.2 ?
S1' C5' H5' 124.2 ?
C2' N6' N7' 116.43(15) y
O9' N7' O8' 123.03(16) y
O9' N7' N6' 115.72(16) y
O8' N7' N6' 121.24(15) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 . 1.721(2) y
S1 C5 . 1.731(2) y
C2 N3 . 1.333(2) y
C2 N6 . 1.356(2) y
N3 C4 . 1.381(2) ?
N3 H3 . 0.8600 ?
C4 C5 . 1.336(3) y
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
N6 N7 . 1.342(2) y
N7 O9 . 1.237(2) y
N7 O8 . 1.250(2) y
S1' C2' . 1.725(2) y
S1' C5' . 1.727(2) y
C2' N3' . 1.335(2) y
C2' N6' . 1.345(2) y
N3' C4' . 1.376(2) ?
N3' H3' . 0.8600 ?
C4' C5' . 1.340(3) y
C4' H4' . 0.9300 ?
C5' H5' . 0.9300 ?
N6' N7' . 1.346(2) y
N7' O9' . 1.236(2) y
N7' O8' . 1.247(2) y
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
_geom_hbond_publ_flag
N3 H3 N6 3_666 0.86 2.05 2.880(2) 163 y
N3' H3' N6' 3 0.86 2.05 2.885(2) 163 y
C4 H4 O9 4_566 0.93 2.54 3.276(2) 136 y
C4' H4' O9' 4_556 0.93 2.59 3.360(2) 141 y
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_publ_flag
C5 S1 C2 N3 0.89(14) ?
C5 S1 C2 N6 179.7(2) ?
N6 C2 N3 C4 -179.91(16) ?
S1 C2 N3 C4 -0.9(2) ?
C2 N3 C4 C5 0.3(2) ?
N3 C4 C5 S1 0.4(2) ?
C2 S1 C5 C4 -0.73(16) ?
N3 C2 N6 N7 -179.69(16) y
S1 C2 N6 N7 1.5(3) y
C2 N6 N7 O9 178.72(16) ?
C2 N6 N7 O8 -0.6(3) ?
C5' S1' C2' N3' -0.58(15) ?
C5' S1' C2' N6' -179.78(19) ?
N6' C2' N3' C4' 179.78(16) ?
S1' C2' N3' C4' 0.4(2) ?
C2' N3' C4' C5' 0.0(2) ?
N3' C4' C5' S1' -0.4(2) ?
C2' S1' C5' C4' 0.59(16) ?
N3' C2' N6' N7' 177.19(15) y
S1' C2' N6' N7' -3.7(3) y
C2' N6' N7' O9' -179.38(16) ?
C2' N6' N7' O8' 0.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10447004
