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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 2.1.    #
#                                                                            #
# 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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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
5-Chloro-4-chloromethyl-2-phenyl-1,3-selenazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H7 Cl2 N Se'
_chemical_formula_sum     'C10 H7 Cl2 N Se'
_chemical_formula_iupac     'C10 H7 Cl2 N Se'
_chemical_formula_weight     291.03
_chemical_melting_point     ?
_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     8.1640(5)
_cell_length_b     10.4050(6)
_cell_length_c     13.7225(7)
_cell_angle_alpha     76.264(3)
_cell_angle_beta     74.357(3)
_cell_angle_gamma     86.475(3)
_cell_volume     1090.39(11)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5903
_cell_measurement_theta_min     1.58
_cell_measurement_theta_max     27.66
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.571
_exptl_crystal_size_mid     0.300
_exptl_crystal_size_min     0.221
_exptl_crystal_density_diffrn     1.773
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     568
_exptl_absorpt_coefficient_mu     3.890
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.256
_exptl_absorpt_correction_T_max     0.423
_exptl_special_details     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX2 area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     17299
_diffrn_reflns_av_R_equivalents     0.0276
_diffrn_reflns_av_sigmaI/netI     0.0305
_diffrn_reflns_theta_min     1.58
_diffrn_reflns_theta_max     27.66
_diffrn_reflns_theta_full     27.66
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     5021
_reflns_number_gt     3550
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_gt     0.0352
_refine_ls_wR_factor_gt     0.0872
_refine_ls_wR_factor_ref     0.0976
_refine_ls_goodness_of_fit_ref     1.025
_refine_ls_restrained_S_all     1.025
_refine_ls_number_reflns     5021
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0445P)²+0.4631P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.420
_refine_diff_density_min     -0.481
_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'
    'Se' 'Se' -0.0929 2.2259
                         '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     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'SMART (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXTL (Bruker, 2004)'
_computing_structure_refinement     SHELXTL
_computing_molecular_graphics     SHELXTL
_computing_publication_material     SHELXTL
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
    Se Se1 1.37993(5) 1.00206(4) -0.11871(3) 0.06946(13) Uani d . 1 . .
    Se Se2 0.72129(4) 0.96216(3) 0.65950(2) 0.06129(12) Uani d . 1 . .
    Cl Cl1 1.2736(2) 1.44955(11) -0.02164(11) 0.1177(5) Uani d . 1 . .
    Cl Cl2 1.43418(18) 1.27694(13) -0.27490(8) 0.1086(4) Uani d . 1 . .
    Cl Cl3 0.56928(17) 0.69066(11) 0.79275(8) 0.1012(4) Uani d . 1 . .
    Cl Cl4 0.70828(12) 0.54767(9) 0.52221(9) 0.0791(3) Uani d . 1 . .
    N N1 1.1682(3) 1.1290(2) 0.01349(19) 0.0552(6) Uani d . 1 . .
    N N2 0.6747(3) 0.8781(2) 0.49813(19) 0.0500(6) Uani d . 1 . .
    C C1 1.1660(6) 1.3615(3) -0.0819(3) 0.0866(12) Uani d . 1 . .
    H H1A 1.0453 1.3592 -0.0477 0.104 Uiso calc R 1 . .
    H H1B 1.1811 1.4075 -0.1540 0.104 Uiso calc R 1 . .
    C C2 1.2296(4) 1.2242(3) -0.0772(3) 0.0601(8) Uani d . 1 . .
    C C3 1.3401(4) 1.1821(3) -0.1550(3) 0.0650(8) Uani d . 1 . .
    C C4 1.2275(3) 1.0130(3) 0.0093(2) 0.0488(6) Uani d . 1 . .
    C C5 1.1829(4) 0.8961(3) 0.0952(2) 0.0498(7) Uani d . 1 . .
    C C6 1.2630(5) 0.7759(3) 0.0919(3) 0.0771(10) Uani d . 1 . .
    H H6A 1.3466 0.7661 0.0329 0.093 Uiso calc R 1 . .
    C C7 1.2180(6) 0.6693(4) 0.1774(4) 0.0937(13) Uani d . 1 . .
    H H7A 1.2740 0.5889 0.1760 0.112 Uiso calc R 1 . .
    C C8 1.0924(6) 0.6819(4) 0.2632(3) 0.0832(11) Uani d . 1 . .
    H H8A 1.0617 0.6098 0.3194 0.100 Uiso calc R 1 . .
    C C9 1.0126(5) 0.7990(4) 0.2667(3) 0.0712(9) Uani d . 1 . .
    H H9A 0.9269 0.8070 0.3254 0.085 Uiso calc R 1 . .
    C C10 1.0572(4) 0.9069(3) 0.1840(2) 0.0577(7) Uani d . 1 . .
    H H10A 1.0027 0.9874 0.1878 0.069 Uiso calc R 1 . .
    C C11 0.5462(4) 0.6569(3) 0.5694(3) 0.0686(9) Uani d . 1 . .
    H H11A 0.4769 0.6834 0.5207 0.082 Uiso calc R 1 . .
    H H11B 0.4733 0.6107 0.6353 0.082 Uiso calc R 1 . .
    C C12 0.6184(3) 0.7770(3) 0.5839(3) 0.0543(7) Uani d . 1 . .
    C C13 0.6302(4) 0.7979(3) 0.6745(3) 0.0599(8) Uani d . 1 . .
    C C14 0.7312(3) 0.9791(3) 0.5186(2) 0.0455(6) Uani d . 1 . .
    C C15 0.7991(3) 1.0989(3) 0.4403(2) 0.0464(6) Uani d . 1 . .
    C C16 0.8770(4) 1.1978(3) 0.4642(3) 0.0589(8) Uani d . 1 . .
    H H16A 0.8828 1.1904 0.5320 0.071 Uiso calc R 1 . .
    C C17 0.9459(4) 1.3072(3) 0.3878(3) 0.0716(10) Uani d . 1 . .
    H H17A 0.9982 1.3731 0.4043 0.086 Uiso calc R 1 . .
    C C18 0.9374(5) 1.3189(3) 0.2881(3) 0.0776(11) Uani d . 1 . .
    H H18A 0.9855 1.3922 0.2367 0.093 Uiso calc R 1 . .
    C C19 0.8585(5) 1.2234(4) 0.2632(3) 0.0740(10) Uani d . 1 . .
    H H19A 0.8515 1.2328 0.1954 0.089 Uiso calc R 1 . .
    C C20 0.7894(4) 1.1132(3) 0.3388(2) 0.0581(8) Uani d . 1 . .
    H H20A 0.7362 1.0484 0.3217 0.070 Uiso calc R 1 . .
_geom_special_details     ?
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
    Se1 C3 . 1.852(4) ?
    Se1 C4 . 1.883(3) ?
    Se2 C13 . 1.851(3) ?
    Se2 C14 . 1.878(3) ?
    Cl1 C1 . 1.773(4) ?
    Cl2 C3 . 1.706(3) ?
    Cl3 C13 . 1.703(3) ?
    Cl4 C11 . 1.779(3) ?
    N1 C4 . 1.282(4) ?
    N1 C2 . 1.386(4) ?
    N2 C14 . 1.291(3) ?
    N2 C12 . 1.372(4) ?
    C1 C2 . 1.482(5) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 C3 . 1.342(5) ?
    C4 C5 . 1.464(4) ?
    C5 C6 . 1.380(4) ?
    C5 C10 . 1.388(4) ?
    C6 C7 . 1.393(6) ?
    C6 H6A . 0.9300 ?
    C7 C8 . 1.364(6) ?
    C7 H7A . 0.9300 ?
    C8 C9 . 1.351(5) ?
    C8 H8A . 0.9300 ?
    C9 C10 . 1.379(5) ?
    C9 H9A . 0.9300 ?
    C10 H10A . 0.9300 ?
    C11 C12 . 1.490(4) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 C13 . 1.341(4) ?
    C14 C15 . 1.464(4) ?
    C15 C16 . 1.386(4) ?
    C15 C20 . 1.389(4) ?
    C16 C17 . 1.380(5) ?
    C16 H16A . 0.9300 ?
    C17 C18 . 1.365(6) ?
    C17 H17A . 0.9300 ?
    C18 C19 . 1.371(5) ?
    C18 H18A . 0.9300 ?
    C19 C20 . 1.381(5) ?
    C19 H19A . 0.9300 ?
    C20 H20A . 0.9300 ?
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
    C3 Se1 C4 . . 83.79(14) ?
    C13 Se2 C14 . . 83.25(13) ?
    C4 N1 C2 . . 113.8(3) ?
    C14 N2 C12 . . 113.7(3) ?
    C2 C1 Cl1 . . 112.0(3) ?
    C2 C1 H1A . . 109.2 ?
    Cl1 C1 H1A . . 109.2 ?
    C2 C1 H1B . . 109.2 ?
    Cl1 C1 H1B . . 109.2 ?
    H1A C1 H1B . . 107.9 ?
    C3 C2 N1 . . 116.1(3) ?
    C3 C2 C1 . . 125.5(3) ?
    N1 C2 C1 . . 118.3(3) ?
    C2 C3 Cl2 . . 126.1(3) ?
    C2 C3 Se1 . . 111.7(2) ?
    Cl2 C3 Se1 . . 122.1(2) ?
    N1 C4 C5 . . 124.1(3) ?
    N1 C4 Se1 . . 114.5(2) ?
    C5 C4 Se1 . . 121.3(2) ?
    C6 C5 C10 . . 118.7(3) ?
    C6 C5 C4 . . 122.4(3) ?
    C10 C5 C4 . . 118.9(3) ?
    C5 C6 C7 . . 119.7(4) ?
    C5 C6 H6A . . 120.2 ?
    C7 C6 H6A . . 120.2 ?
    C8 C7 C6 . . 120.5(4) ?
    C8 C7 H7A . . 119.7 ?
    C6 C7 H7A . . 119.7 ?
    C9 C8 C7 . . 120.1(4) ?
    C9 C8 H8A . . 119.9 ?
    C7 C8 H8A . . 119.9 ?
    C8 C9 C10 . . 120.5(4) ?
    C8 C9 H9A . . 119.7 ?
    C10 C9 H9A . . 119.7 ?
    C9 C10 C5 . . 120.5(3) ?
    C9 C10 H10A . . 119.8 ?
    C5 C10 H10A . . 119.8 ?
    C12 C11 Cl4 . . 111.8(2) ?
    C12 C11 H11A . . 109.3 ?
    Cl4 C11 H11A . . 109.3 ?
    C12 C11 H11B . . 109.3 ?
    Cl4 C11 H11B . . 109.3 ?
    H11A C11 H11B . . 107.9 ?
    C13 C12 N2 . . 115.9(3) ?
    C13 C12 C11 . . 125.9(3) ?
    N2 C12 C11 . . 118.1(3) ?
    C12 C13 Cl3 . . 126.1(3) ?
    C12 C13 Se2 . . 112.4(2) ?
    Cl3 C13 Se2 . . 121.5(2) ?
    N2 C14 C15 . . 124.0(3) ?
    N2 C14 Se2 . . 114.8(2) ?
    C15 C14 Se2 . . 121.2(2) ?
    C16 C15 C20 . . 118.8(3) ?
    C16 C15 C14 . . 121.7(3) ?
    C20 C15 C14 . . 119.5(3) ?
    C17 C16 C15 . . 120.4(3) ?
    C17 C16 H16A . . 119.8 ?
    C15 C16 H16A . . 119.8 ?
    C18 C17 C16 . . 120.1(3) ?
    C18 C17 H17A . . 120.0 ?
    C16 C17 H17A . . 120.0 ?
    C17 C18 C19 . . 120.4(3) ?
    C17 C18 H18A . . 119.8 ?
    C19 C18 H18A . . 119.8 ?
    C18 C19 C20 . . 120.1(4) ?
    C18 C19 H19A . . 120.0 ?
    C20 C19 H19A . . 120.0 ?
    C19 C20 C15 . . 120.2(3) ?
    C19 C20 H20A . . 119.9 ?
    C15 C20 H20A . . 119.9 ?
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
    C4 N1 C2 C3 . . . . 0.2(4) ?
    C4 N1 C2 C1 . . . . 178.5(3) ?
    Cl1 C1 C2 C3 . . . . -100.3(4) ?
    Cl1 C1 C2 N1 . . . . 81.6(4) ?
    N1 C2 C3 Cl2 . . . . 179.5(2) ?
    C1 C2 C3 Cl2 . . . . 1.3(5) ?
    N1 C2 C3 Se1 . . . . 0.4(4) ?
    C1 C2 C3 Se1 . . . . -177.8(3) ?
    C4 Se1 C3 C2 . . . . -0.6(2) ?
    C4 Se1 C3 Cl2 . . . . -179.7(2) ?
    C2 N1 C4 C5 . . . . 179.6(3) ?
    C2 N1 C4 Se1 . . . . -0.6(3) ?
    C3 Se1 C4 N1 . . . . 0.7(2) ?
    C3 Se1 C4 C5 . . . . -179.5(2) ?
    N1 C4 C5 C6 . . . . -172.8(3) ?
    Se1 C4 C5 C6 . . . . 7.4(4) ?
    N1 C4 C5 C10 . . . . 6.2(4) ?
    Se1 C4 C5 C10 . . . . -173.6(2) ?
    C10 C5 C6 C7 . . . . -0.8(5) ?
    C4 C5 C6 C7 . . . . 178.2(3) ?
    C5 C6 C7 C8 . . . . 1.7(6) ?
    C6 C7 C8 C9 . . . . -1.2(7) ?
    C7 C8 C9 C10 . . . . -0.1(6) ?
    C8 C9 C10 C5 . . . . 1.1(5) ?
    C6 C5 C10 C9 . . . . -0.6(4) ?
    C4 C5 C10 C9 . . . . -179.6(3) ?
    C14 N2 C12 C13 . . . . 0.0(4) ?
    C14 N2 C12 C11 . . . . 178.4(2) ?
    Cl4 C11 C12 C13 . . . . -100.8(3) ?
    Cl4 C11 C12 N2 . . . . 81.0(3) ?
    N2 C12 C13 Cl3 . . . . 179.6(2) ?
    C11 C12 C13 Cl3 . . . . 1.4(5) ?
    N2 C12 C13 Se2 . . . . 0.2(3) ?
    C11 C12 C13 Se2 . . . . -178.1(2) ?
    C14 Se2 C13 C12 . . . . -0.2(2) ?
    C14 Se2 C13 Cl3 . . . . -179.7(2) ?
    C12 N2 C14 C15 . . . . 179.6(2) ?
    C12 N2 C14 Se2 . . . . -0.2(3) ?
    C13 Se2 C14 N2 . . . . 0.2(2) ?
    C13 Se2 C14 C15 . . . . -179.6(2) ?
    N2 C14 C15 C16 . . . . -172.1(3) ?
    Se2 C14 C15 C16 . . . . 7.7(4) ?
    N2 C14 C15 C20 . . . . 6.4(4) ?
    Se2 C14 C15 C20 . . . . -173.8(2) ?
    C20 C15 C16 C17 . . . . -1.1(4) ?
    C14 C15 C16 C17 . . . . 177.4(3) ?
    C15 C16 C17 C18 . . . . 0.2(5) ?
    C16 C17 C18 C19 . . . . 0.9(5) ?
    C17 C18 C19 C20 . . . . -1.1(6) ?
    C18 C19 C20 C15 . . . . 0.2(5) ?
    C16 C15 C20 C19 . . . . 0.9(4) ?
    C14 C15 C20 C19 . . . . -177.6(3) ?
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
    C1 H1B Cl2 . 0.97 2.78 3.213(5) 107.7 yes
    C6 H6A Se1 . 0.93 2.79 3.219(4) 109.3 yes
    C11 H11B Cl3 . 0.97 2.80 3.222(4) 107.4 yes
    C16 H16A Se2 . 0.93 2.76 3.200(3) 110.2 yes
data_global
_journal_date_recd_electronic     2007-07-04
_journal_date_accepted     2007-07-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      8
_journal_page_first     o3642
_journal_page_last     o3642
_journal_paper_category     QO
_journal_coeditor_code     BH2124
_publ_contact_author_name     'Guo-Liang Zhao'
_publ_contact_author_address
;
Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces
Institute of Physical Chemistry
Zhejiang Normal University
Jinhua
Zhejiang 321004
People's Republic of China
;
_publ_contact_author_email     sky53@zjnu.cn
_publ_contact_author_fax     '86-579-2282595'
_publ_contact_author_phone     '86-579-2283925'
_publ_section_title
;
5-Chloro-4-chloromethyl-2-phenyl-1,3-selenazole
;
loop_
    _publ_author_name
    _publ_author_address
    "Shi, Xia"
;
College of Chemistry and Life Science
Zhejiang Normal University
Jinhua 321004
Zhejiang
People's Republic of China
;
    "Zhao, Guo-Liang"
;
Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces
Institute of Physical Chemistry
Zhejiang Normal University
Jinhua 321004
Zhejiang
People's Republic of China
and College of Chemistry and Life Science
Zhejiang Normal University
Jinhua 321004
Zhejiang
People's Republic of China
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