##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Ethyl 2-{3-[(2-chloro-1,3-thiazol-5-yl)methyl]-
4-nitroimino-1,3,5-triazinan-1-yl}acetate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H15 Cl N6 O4 S'
_chemical_formula_sum     'C11 H15 Cl N6 O4 S'
_chemical_formula_iupac     'C11 H15 Cl N6 O4 S'
_chemical_formula_weight     362.81
_chemical_melting_point     449
_symmetry_cell_setting     'Triclinic'
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.5066(6)
_cell_length_b     9.1114(7)
_cell_length_c     10.9071(8)
_cell_angle_alpha     100.488(2)
_cell_angle_beta     98.416(3)
_cell_angle_gamma     101.281(3)
_cell_volume     800.55(10)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2512
_cell_measurement_theta_min     2.34
_cell_measurement_theta_max     28.22
_cell_measurement_temperature     298(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.23
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.505
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     376
_exptl_absorpt_coefficient_mu     0.398
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.8570
_exptl_absorpt_correction_T_max     0.9246
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine focus sealed Siemens Mo tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     '0.3° wide ω scans'
_diffrn_detector_area_resol_mean     '1.57 \\times 0.49 mm'
_diffrn_reflns_number     5350
_diffrn_reflns_av_R_equivalents     0.0748
_diffrn_reflns_av_sigmaI/netI     0.0683
_diffrn_reflns_theta_min     1.93
_diffrn_reflns_theta_max     26.50
_diffrn_reflns_theta_full     26.50
_diffrn_measured_fraction_theta_max     0.984
_diffrn_measured_fraction_theta_full     0.984
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     12
_reflns_number_total     3259
_reflns_number_gt     2670
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     'Fsqd'
_refine_ls_matrix_type     'full'
_refine_ls_R_factor_all     0.0572
_refine_ls_R_factor_gt     0.0469
_refine_ls_wR_factor_gt     0.1215
_refine_ls_wR_factor_ref     0.1278
_refine_ls_goodness_of_fit_ref     1.046
_refine_ls_restrained_S_all     1.046
_refine_ls_number_reflns     3259
_refine_ls_number_parameters     212
_refine_ls_number_restraints     9
_refine_ls_hydrogen_treatment     'mixed'
_refine_ls_weighting_scheme     'calc'
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0598P)²+0.0779P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     'geom'
_atom_sites_solution_primary     'direct'
_atom_sites_solution_secondary     'difmap'
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.311
_refine_diff_density_min     -0.260
_refine_ls_extinction_method     'none'
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'PLATON (Spek, 2009)'
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_disorder_assembly
    _atom_site_disorder_group
    C C1 -0.0095(3) 0.7149(2) 0.26414(19) 0.0444(5) Uani d . 1 . .
    H H1A 0.0880 0.7030 0.2309 0.053 Uiso calc R 1 . .
    H H1B -0.0751 0.7574 0.2054 0.053 Uiso calc R 1 . .
    C C2 -0.1049(2) 0.5590(2) 0.2702(2) 0.0454(5) Uani d . 1 . .
    C C3 -0.2096(4) 0.3054(3) 0.1509(3) 0.0701(7) Uani d U 1 . .
    H H3C -0.3189 0.3031 0.1674 0.084 Uiso calc R 1 . .
    H H3B -0.1526 0.2605 0.2128 0.084 Uiso calc R 1 . .
    C C4 -0.2173(5) 0.2185(3) 0.0216(3) 0.0943(11) Uani d U 1 . .
    H H4A -0.2647 0.2692 -0.0391 0.141 Uiso calc R 1 . .
    H H4B -0.2831 0.1169 0.0105 0.141 Uiso calc R 1 . .
    H H4C -0.1091 0.2126 0.0092 0.141 Uiso calc R 1 . .
    C C5 0.1108(3) 0.9754(2) 0.3748(2) 0.0485(5) Uani d . 1 . .
    H H5A 0.1225 1.0469 0.4549 0.058 Uiso calc R 1 . .
    H H5B 0.0397 1.0059 0.3108 0.058 Uiso calc R 1 . .
    C C6 0.1510(2) 0.7783(2) 0.47718(18) 0.0405(4) Uani d . 1 . .
    H H6A 0.1079 0.6734 0.4825 0.049 Uiso calc R 1 . .
    H H6B 0.1619 0.8435 0.5603 0.049 Uiso calc R 1 . .
    C C7 0.3648(2) 0.88803(19) 0.36999(17) 0.0337(4) Uani d . 1 . .
    C C8 0.4008(2) 0.6726(2) 0.46817(19) 0.0408(4) Uani d . 1 . .
    H H8A 0.3775 0.6440 0.5462 0.049 Uiso calc R 1 . .
    H H8B 0.5174 0.7146 0.4805 0.049 Uiso calc R 1 . .
    C C9 0.3537(2) 0.5325(2) 0.36264(18) 0.0399(4) Uani d . 1 . .
    C C10 0.2576(3) 0.3953(2) 0.3607(2) 0.0468(5) Uani d . 1 . .
    H H10 0.2113 0.3768 0.4302 0.056 Uiso calc R 1 . .
    C C11 0.3072(3) 0.3403(2) 0.1709(2) 0.0527(6) Uani d . 1 . .
    Cl Cl1 0.30601(10) 0.23735(8) 0.02224(6) 0.0779(3) Uani d . 1 . .
    N N1 0.03775(19) 0.82249(18) 0.38653(16) 0.0408(4) Uani d . 1 . .
    N N2 0.31341(19) 0.79068(17) 0.44198(15) 0.0367(4) Uani d . 1 . .
    N N3 0.2716(2) 0.98200(18) 0.33909(17) 0.0393(4) Uani d . 1 . .
    H H3A 0.306(3) 1.039(3) 0.297(2) 0.047 Uiso d . 1 . .
    N N4 0.50886(19) 0.87424(18) 0.33519(16) 0.0402(4) Uani d . 1 . .
    N N5 0.5757(2) 0.97002(19) 0.26754(16) 0.0430(4) Uani d . 1 . .
    N N6 0.2308(2) 0.28347(19) 0.25118(19) 0.0544(5) Uani d . 1 . .
    O O1 -0.1559(2) 0.52487(19) 0.36034(15) 0.0659(5) Uani d . 1 . .
    O O2 -0.1227(2) 0.46316(17) 0.16030(15) 0.0614(4) Uani d U 1 . .
    O O3 0.5158(2) 1.0752(2) 0.23700(19) 0.0671(5) Uani d . 1 . .
    O O4 0.70673(19) 0.95104(19) 0.23875(17) 0.0607(4) Uani d . 1 . .
    S S1 0.41711(8) 0.52681(6) 0.21876(5) 0.0532(2) Uani d . 1 . .
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
 estimated using the full covariance matrix. The cell s.u.'s are taken into
 account individually in the estimation of s.u.'s in distances, angles and
 torsion angles; correlations between s.u.'s in cell parameters are only used
 when they are defined by crystal symmetry. An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
    C1 N1 . 1.455(3) ?
    C1 C2 . 1.510(3) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 O1 . 1.198(2) ?
    C2 O2 . 1.318(3) ?
    C3 O2 . 1.460(3) ?
    C3 C4 . 1.472(4) ?
    C3 H3C . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 H4A . 0.9600 ?
    C4 H4B . 0.9600 ?
    C4 H4C . 0.9600 ?
    C5 N1 . 1.447(2) ?
    C5 N3 . 1.469(3) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 N1 . 1.444(3) ?
    C6 N2 . 1.476(2) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 N3 . 1.329(2) ?
    C7 N2 . 1.340(2) ?
    C7 N4 . 1.357(2) ?
    C8 N2 . 1.468(2) ?
    C8 C9 . 1.498(3) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 C10 . 1.348(3) ?
    C9 S1 . 1.728(2) ?
    C10 N6 . 1.380(3) ?
    C10 H10 . 0.9300 ?
    C11 N6 . 1.287(3) ?
    C11 S1 . 1.717(2) ?
    C11 Cl1 . 1.717(2) ?
    N3 H3A . 0.79(2) ?
    N4 N5 . 1.339(2) ?
    N5 O4 . 1.237(2) ?
    N5 O3 . 1.243(2) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 C1 C2 . . 113.48(16) ?
    N1 C1 H1A . . 108.9 ?
    C2 C1 H1A . . 108.9 ?
    N1 C1 H1B . . 108.9 ?
    C2 C1 H1B . . 108.9 ?
    H1A C1 H1B . . 107.7 ?
    O1 C2 O2 . . 124.32(19) ?
    O1 C2 C1 . . 126.2(2) ?
    O2 C2 C1 . . 109.47(17) ?
    O2 C3 C4 . . 108.0(2) ?
    O2 C3 H3C . . 110.1 ?
    C4 C3 H3C . . 110.1 ?
    O2 C3 H3B . . 110.1 ?
    C4 C3 H3B . . 110.1 ?
    H3C C3 H3B . . 108.4 ?
    C3 C4 H4A . . 109.5 ?
    C3 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    C3 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    N1 C5 N3 . . 111.07(15) ?
    N1 C5 H5A . . 109.4 ?
    N3 C5 H5A . . 109.4 ?
    N1 C5 H5B . . 109.4 ?
    N3 C5 H5B . . 109.4 ?
    H5A C5 H5B . . 108.0 ?
    N1 C6 N2 . . 112.02(15) ?
    N1 C6 H6A . . 109.2 ?
    N2 C6 H6A . . 109.2 ?
    N1 C6 H6B . . 109.2 ?
    N2 C6 H6B . . 109.2 ?
    H6A C6 H6B . . 107.9 ?
    N3 C7 N2 . . 118.48(17) ?
    N3 C7 N4 . . 127.89(17) ?
    N2 C7 N4 . . 113.62(16) ?
    N2 C8 C9 . . 112.19(16) ?
    N2 C8 H8A . . 109.2 ?
    C9 C8 H8A . . 109.2 ?
    N2 C8 H8B . . 109.2 ?
    C9 C8 H8B . . 109.2 ?
    H8A C8 H8B . . 107.9 ?
    C10 C9 C8 . . 127.86(19) ?
    C10 C9 S1 . . 109.13(15) ?
    C8 C9 S1 . . 123.00(14) ?
    C9 C10 N6 . . 117.05(19) ?
    C9 C10 H10 . . 121.5 ?
    N6 C10 H10 . . 121.5 ?
    N6 C11 S1 . . 117.24(17) ?
    N6 C11 Cl1 . . 123.01(18) ?
    S1 C11 Cl1 . . 119.74(15) ?
    C6 N1 C5 . . 107.68(16) ?
    C6 N1 C1 . . 113.41(16) ?
    C5 N1 C1 . . 111.93(16) ?
    C7 N2 C8 . . 121.33(16) ?
    C7 N2 C6 . . 120.93(15) ?
    C8 N2 C6 . . 116.72(15) ?
    C7 N3 C5 . . 122.00(17) ?
    C7 N3 H3A . . 115.8(16) ?
    C5 N3 H3A . . 122.2(16) ?
    N5 N4 C7 . . 118.95(16) ?
    O4 N5 O3 . . 120.48(17) ?
    O4 N5 N4 . . 115.65(17) ?
    O3 N5 N4 . . 123.84(16) ?
    C11 N6 C10 . . 108.32(18) ?
    C2 O2 C3 . . 116.56(17) ?
    C11 S1 C9 . . 88.24(10) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N1 C1 C2 O1 . . . . 7.9(3) ?
    N1 C1 C2 O2 . . . . -171.21(18) ?
    N2 C8 C9 C10 . . . . -105.2(2) ?
    N2 C8 C9 S1 . . . . 73.8(2) ?
    C8 C9 C10 N6 . . . . 179.47(18) ?
    S1 C9 C10 N6 . . . . 0.3(2) ?
    N2 C6 N1 C5 . . . . -55.1(2) ?
    N2 C6 N1 C1 . . . . 69.28(19) ?
    N3 C5 N1 C6 . . . . 56.0(2) ?
    N3 C5 N1 C1 . . . . -69.3(2) ?
    C2 C1 N1 C6 . . . . 65.1(2) ?
    C2 C1 N1 C5 . . . . -172.82(16) ?
    N3 C7 N2 C8 . . . . 173.29(16) ?
    N4 C7 N2 C8 . . . . -5.4(2) ?
    N3 C7 N2 C6 . . . . 5.2(3) ?
    N4 C7 N2 C6 . . . . -173.49(16) ?
    C9 C8 N2 C7 . . . . -82.8(2) ?
    C9 C8 N2 C6 . . . . 85.8(2) ?
    N1 C6 N2 C7 . . . . 25.6(2) ?
    N1 C6 N2 C8 . . . . -143.03(17) ?
    N2 C7 N3 C5 . . . . -3.8(3) ?
    N4 C7 N3 C5 . . . . 174.62(18) ?
    N1 C5 N3 C7 . . . . -28.0(3) ?
    N3 C7 N4 N5 . . . . 4.3(3) ?
    N2 C7 N4 N5 . . . . -177.22(16) ?
    C7 N4 N5 O4 . . . . -179.85(17) ?
    C7 N4 N5 O3 . . . . 2.1(3) ?
    S1 C11 N6 C10 . . . . 0.8(2) ?
    Cl1 C11 N6 C10 . . . . 179.62(16) ?
    C9 C10 N6 C11 . . . . -0.7(3) ?
    O1 C2 O2 C3 . . . . -0.5(4) ?
    C1 C2 O2 C3 . . . . 178.7(2) ?
    C4 C3 O2 C2 . . . . 179.5(2) ?
    N6 C11 S1 C9 . . . . -0.57(19) ?
    Cl1 C11 S1 C9 . . . . -179.41(14) ?
    C10 C9 S1 C11 . . . . 0.11(16) ?
    C8 C9 S1 C11 . . . . -179.09(17) ?
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
    N3 H3A N6 1_565 0.79(2) 2.55(2) 3.133(2) 132(2)
    N3 H3A O3 . 0.79(2) 1.98(2) 2.570(2) 131(2)
    C3 H3C O3 1_445 0.97 2.57 3.191(3) 121.9
    C5 H5A N1 2_576 0.97 2.61 3.449(3) 144.2
    C6 H6B O4 2_676 0.97 2.56 3.478(3) 159.0
    C10 H10 O1 2_566 0.93 2.45 3.278(3) 149.0
data_global
_journal_date_recd_electronic     2010-04-11
_journal_date_accepted     2010-05-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      6
_journal_page_first     o1457
_journal_page_last     o1458
_journal_paper_category     QO
_journal_coeditor_code     RK2201
_publ_contact_author_name     'Doctor C.W. Sun'
_publ_contact_author_address
;
Department of Chemistry
College of Life and Environmental Science
Shanghai Normal University
Shanghai, 200234
People's Republic of China
;
_publ_contact_author_email     willin112@163.com
_publ_contact_author_fax     '86-21-64321926'
_publ_contact_author_phone     '86-21-64321926'
_publ_section_title
;\
Ethyl
2-{3-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-nitroimino-1,3,5-triazinan-1-yl}\
acetate
;
loop_
    _publ_author_name
    _publ_author_address
    'Sun, Chuan-wen'
;
Department of Chemistry
College of Life and Environmental Science
Shanghai Normal University
Shanghai 200234
People's Republic of China
;
    'Zhu, Jun'
;
Department of Chemistry
College of Life and Environmental Science
Shanghai Normal University
Shanghai 200234
People's Republic of China
;
    'Jin, Jia'
;
Department of Chemistry
College of Life and Environmental Science
Shanghai Normal University
Shanghai 200234
People's Republic of China
;
    'Yang, Ding-rong'
;
Department of Chemistry
College of Life and Environmental Science
Shanghai Normal University
Shanghai 200234
People's Republic of China
;
