#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/62/2236226.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_2236226
loop_
_publ_author_name
'Kant, Rajni'
'Gupta, Vivek K.'
'Kapoor, Kamini'
'Shripanavar, Chetan S.'
'Banerjee, Kaushik'
_publ_section_title
;
 3-[(2-Chloro-1,3-thiazol-5-yl)methyl]-5-methyl-1,3,5-oxadiazinan-4-one
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3109
_journal_paper_doi               10.1107/S1600536812042031
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H10 Cl N3 O2 S'
_chemical_formula_moiety         'C8 H10 Cl N3 O2 S'
_chemical_formula_sum            'C8 H10 Cl N3 O2 S'
_chemical_formula_weight         247.70
_chemical_name_systematic
;
3-[(2-Chloro-1,3-thiazol-5-yl)methyl]-5-methyl-1,3,5-oxadiazinan-4-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6141(2)
_cell_length_b                   11.7335(4)
_cell_length_c                   20.1460(8)
_cell_measurement_reflns_used    11280
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.00
_cell_measurement_theta_min      3.47
_cell_volume                     1090.70(7)
_computing_cell_refinement       'CrysAlis PRO  (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO  (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis PRO  (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1049
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Sapphire3'
_diffrn_measurement_method       'omega scan'
_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  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22323
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.47
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.158
_refine_ls_abs_structure_details 'Flack (1983), 856 Friedel pairs'
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0314
_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)+(0.0399P)²+0.2799P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                1974
_reflns_number_total             2147
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            gk2519.cif
_cod_data_source_block           I
_cod_database_code               2236226
_cod_database_fobs_code          2236226
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.29172(13) 0.85031(5) 0.83926(3) 0.04611(15) Uani d . 1 1
Cl Cl1 0.64157(15) 0.83860(6) 0.96232(3) 0.0642(2) Uani d . 1 1
O O1 0.4809(4) 1.08899(16) 0.64448(10) 0.0653(5) Uani d . 1 1
C C2 0.2262(7) 1.1021(2) 0.68003(16) 0.0668(8) Uani d . 1 1
H H2A 0.0844 1.1412 0.6527 0.080 Uiso calc R 1 1
H H2B 0.2630 1.1487 0.7189 0.080 Uiso calc R 1 1
N N3 0.1108(5) 0.99332(17) 0.70052(10) 0.0512(5) Uani d . 1 1
C C4 0.1836(6) 0.8940(2) 0.67011(12) 0.0516(6) Uani d . 1 1
N N5 0.3433(6) 0.90503(19) 0.61443(11) 0.0640(6) Uani d . 1 1
C C6 0.4364(9) 1.0158(3) 0.59173(14) 0.0778(9) Uani d . 1 1
H H6A 0.6149 1.0079 0.5667 0.093 Uiso calc R 1 1
H H6B 0.2905 1.0475 0.5624 0.093 Uiso calc R 1 1
C C7 -0.0657(6) 0.9905(3) 0.76014(14) 0.0613(7) Uani d . 1 1
H H7A -0.2048 0.9289 0.7564 0.074 Uiso calc R 1 1
H H7B -0.1734 1.0613 0.7634 0.074 Uiso calc R 1 1
O O7 0.1066(5) 0.80128(15) 0.69297(10) 0.0744(6) Uani d . 1 1
C C8 0.4470(9) 0.8075(3) 0.57872(19) 0.0975(12) Uani d . 1 1
H H8A 0.3872 0.7392 0.6012 0.146 Uiso calc R 1 1
H H8B 0.6547 0.8098 0.5765 0.146 Uiso calc R 1 1
H H8C 0.3684 0.8080 0.5346 0.146 Uiso calc R 1 1
C C9 0.1052(5) 0.9747(2) 0.82176(12) 0.0494(6) Uani d . 1 1
C C10 0.4123(5) 0.9127(2) 0.91085(12) 0.0484(6) Uani d . 1 1
N N11 0.3276(6) 1.01443(19) 0.92255(12) 0.0692(7) Uani d . 1 1
C C12 0.1516(7) 1.0488(2) 0.87096(15) 0.0680(8) Uani d . 1 1
H H12 0.0683 1.1210 0.8704 0.082 Uiso calc R 1 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'
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
C10 S1 C9 88.42(12)
C6 O1 C2 109.9(2)
O1 C2 N3 111.3(2)
O1 C2 H2A 109.4
N3 C2 H2A 109.4
O1 C2 H2B 109.4
N3 C2 H2B 109.4
H2A C2 H2B 108.0
C4 N3 C2 122.6(2)
C4 N3 C7 119.5(2)
C2 N3 C7 117.6(2)
O7 C4 N5 123.6(2)
O7 C4 N3 121.1(2)
N5 C4 N3 115.3(2)
C4 N5 C8 121.5(3)
C4 N5 C6 120.9(2)
C8 N5 C6 117.4(3)
O1 C6 N5 111.1(2)
O1 C6 H6A 109.4
N5 C6 H6A 109.4
O1 C6 H6B 109.4
N5 C6 H6B 109.4
H6A C6 H6B 108.0
N3 C7 C9 113.4(2)
N3 C7 H7A 108.9
C9 C7 H7A 108.9
N3 C7 H7B 108.9
C9 C7 H7B 108.9
H7A C7 H7B 107.7
N5 C8 H8A 109.5
N5 C8 H8B 109.5
H8A C8 H8B 109.5
N5 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C12 C9 C7 128.7(2)
C12 C9 S1 108.5(2)
C7 C9 S1 122.7(2)
N11 C10 S1 117.1(2)
N11 C10 Cl1 123.4(2)
S1 C10 Cl1 119.52(14)
C10 N11 C12 108.3(2)
C9 C12 N11 117.6(2)
C9 C12 H12 121.2
N11 C12 H12 121.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C10 1.710(2)
S1 C9 1.731(2)
Cl1 C10 1.718(3)
O1 C6 1.382(4)
O1 C2 1.385(4)
C2 N3 1.443(3)
C2 H2A 0.9700
C2 H2B 0.9700
N3 C4 1.359(3)
N3 C7 1.452(3)
C4 O7 1.233(3)
C4 N5 1.348(3)
N5 C8 1.434(4)
N5 C6 1.443(4)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C9 1.482(4)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C12 1.336(4)
C10 N11 1.278(3)
N11 C12 1.379(4)
C12 H12 0.9300
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
C12 H12 O7 3_556 0.93 2.60 3.443(3) 151 yes
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 O1 C2 N3 54.5(3)
O1 C2 N3 C4 -20.9(4)
O1 C2 N3 C7 152.7(2)
C2 N3 C4 O7 172.1(3)
C7 N3 C4 O7 -1.3(4)
C2 N3 C4 N5 -7.7(4)
C7 N3 C4 N5 178.8(2)
O7 C4 N5 C8 -2.7(5)
N3 C4 N5 C8 177.2(3)
O7 C4 N5 C6 -177.5(3)
N3 C4 N5 C6 2.4(4)
C2 O1 C6 N5 -59.9(4)
C4 N5 C6 O1 31.4(4)
C8 N5 C6 O1 -143.6(3)
C4 N3 C7 C9 85.9(3)
C2 N3 C7 C9 -87.9(3)
N3 C7 C9 C12 111.4(3)
N3 C7 C9 S1 -66.6(3)
C10 S1 C9 C12 -0.2(2)
C10 S1 C9 C7 178.1(2)
C9 S1 C10 N11 0.3(2)
C9 S1 C10 Cl1 -178.75(16)
S1 C10 N11 C12 -0.2(3)
Cl1 C10 N11 C12 178.8(2)
C7 C9 C12 N11 -178.0(3)
S1 C9 C12 N11 0.2(4)
C10 N11 C12 C9 0.0(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658063
