data_2006179
_journal_name_full 'Acta Crystallographica'
_journal_year 1997
_journal_volume C53
_journal_page_first 797
_journal_page_last 799
_publ_section_title
;
N-(2,3,5,6-Tetrachloropyrid-4-yl)cinnamide
;
loop_
_publ_author_name
 'Clegg, William'
 'Elsegood, Mark R. J.'
 'Jackson, Richard F. W.'
 'Fraser, Joanne L.'
 'Emsden, Lee J.'
_chemical_formula_sum 'C14 H8 Cl4 N2 O'
_chemical_formula_weight 362.02
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
_cell_length_a 11.437(2)
_cell_length_b 7.5790(10)
_cell_length_c 17.335(2)
_cell_angle_alpha 90.00
_cell_angle_beta 95.09(3)
_cell_angle_gamma 90.00
_cell_volume 1496.7(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 160(2)
_exptl_crystal_density_diffrn 1.607
_diffrn_ambient_temperature 160(2)
_refine_ls_R_factor_obs  .0464
_refine_ls_wR_factor_obs  .1177
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
 C1  .3059(2)  .3223(3)  .51630(16)  .0285(6) Uani d . 1 . C
 C2  .2735(2)  .3866(4)  .44261(16)  .0295(6) Uani d . 1 . C
 Cl2  .13344(7)  .46301(12)  .41995(5)  .0476(2) Uani d . 1 . Cl
 C3  .3580(2)  .3891(4)  .38982(15)  .0300(6) Uani d . 1 . C
 Cl3  .32432(8)  .46992(11)  .29785(4)  .0466(2) Uani d . 1 . Cl
 N1  .4666(2)  .3304(3)  .40650(13)  .0303(5) Uani d . 1 . N
 C4  .4960(2)  .2687(3)  .47684(16)  .0282(6) Uani d . 1 . C
 Cl4  .63850(6)  .19321(10)  .49473(5)  .0395(2) Uani d . 1 . Cl
 C5  .4195(2)  .2626(4)  .53496(15)  .0284(6) Uani d . 1 . C
 Cl5  .46046(7)  .18428(11)  .62573(4)  .0435(2) Uani d . 1 . Cl
 O  .15025(17)  .0702(3)  .52660(11)  .0345(5) Uani d . 1 . O
 N2  .22866(17)  .3258(3)  .57234(11)  .0214(5) Uani d . 1 . N
 H2  .2288  .4124  .6062  .026 Uiso calc R 1 . H
 C6  .1502(2)  .1864(4)  .57327(15)  .0271(6) Uani d . 1 . C
 C7  .0751(2)  .2094(4)  .63657(16)  .0284(6) Uani d . 1 . C
 H7  .0936  .2955  .6756  .034 Uiso calc R 1 . H
 C8  -.0198(2)  .1077(4)  .63875(15)  .0272(6) Uani d . 1 . C
 H8  -.0329  .0232  .5985  .033 Uiso calc R 1 . H
 C9  -.1056(2)  .1120(3)  .69624(15)  .0267(6) Uani d . 1 . C
 C10  -.0880(2)  .2073(4)  .76556(15)  .0303(6) Uani d . 1 . C
 H10  -.0169  .2706  .7771  .036 Uiso calc R 1 . H
 C11  -.1734(3)  .2098(4)  .81736(17)  .0356(7) Uani d . 1 . C
 H11  -.1607  .2753  .8641  .043 Uiso calc R 1 . H
 C12  -.2771(3)  .1176(4)  .80153(17)  .0350(7) Uani d . 1 . C
 H12  -.3357  .1206  .8371  .042 Uiso calc R 1 . H
 C13  -.2953(3)  .0205(4)  .73366(17)  .0352(7) Uani d . 1 . C
 H13  -.3661  -.0442  .7229  .042 Uiso calc R 1 . H
 C14  -.2101(2)  .0182(4)  .68153(16)  .0312(6) Uani d . 1 . C
 H14  -.2231  -.0483  .6351  .037 Uiso calc R 1 . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
 C1  .0309(14)  .0252(13)  .0301(13)  -.0060(11)  .0077(11)  -.0054(11)
 C2  .0266(13)  .0262(14)  .0357(14)  .0011(11)  .0022(11)  -.0012(11)
 Cl2  .0303(4)  .0544(5)  .0577(5)  .0108(3)  .0016(3)  .0048(4)
 C3  .0348(14)  .0259(14)  .0294(14)  -.0003(11)  .0031(11)  .0015(11)
 Cl3  .0588(5)  .0496(5)  .0313(4)  .0007(4)  .0029(3)  .0113(3)
 N1  .0341(12)  .0262(12)  .0319(12)  -.0029(10)  .0109(10)  .0004(10)
 C4  .0269(13)  .0227(13)  .0356(14)  -.0002(10)  .0062(12)  -.0024(11)
 Cl4  .0269(4)  .0379(4)  .0538(5)  .0047(3)  .0049(3)  -.0008(3)
 C5  .0320(14)  .0275(14)  .0260(13)  -.0038(11)  .0044(11)  -.0020(11)
 Cl5  .0507(5)  .0511(5)  .0278(4)  -.0019(4)  -.0012(3)  .0058(3)
 O  .0321(10)  .0365(11)  .0365(11)  -.0038(8)  .0125(8)  -.0106(9)
 N2  .0229(10)  .0236(11)  .0199(10)  -.0085(8)  .0143(8)  -.0128(8)
 C6  .0243(13)  .0308(14)  .0261(13)  .0019(10)  .0014(11)  -.0023(11)
 C7  .0268(13)  .0319(14)  .0272(13)  .0015(11)  .0066(11)  -.0046(11)
 C8  .0278(13)  .0282(14)  .0259(13)  .0026(11)  .0043(11)  -.0019(11)
 C9  .0263(13)  .0264(13)  .0275(13)  .0035(11)  .0042(10)  .0029(11)
 C10  .0308(14)  .0329(15)  .0280(14)  -.0020(11)  .0065(11)  -.0019(11)
 C11  .0439(17)  .0348(16)  .0297(14)  .0025(13)  .0118(13)  -.0017(12)
 C12  .0331(15)  .0378(16)  .0362(15)  .0076(12)  .0150(12)  .0120(13)
 C13  .0268(14)  .0379(16)  .0412(16)  -.0007(12)  .0051(12)  .0093(13)
 C14  .0299(14)  .0340(15)  .0299(14)  -.0016(11)  .0033(11)  .0001(12)
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 N2 . 1.370(3) no
 C1 C2 . 1.387(4) no
 C1 C5 . 1.387(4) no
 C2 C3 . 1.389(4) no
 C2 Cl2 . 1.715(3) no
 C3 N1 . 1.327(4) no
 C3 Cl3 . 1.719(3) no
 N1 C4 . 1.322(4) no
 C4 C5 . 1.393(4) no
 C4 Cl4 . 1.729(3) no
 C5 Cl5 . 1.708(3) no
 O C6 . 1.196(3) yes
 N2 C6 . 1.387(3) yes
 C6 C7 . 1.463(4) yes
 C7 C8 . 1.334(4) yes
 C8 C9 . 1.460(4) no
 C9 C14 . 1.395(4) no
 C9 C10 . 1.401(4) no
 C10 C11 . 1.384(4) no
 C11 C12 . 1.383(4) no
 C12 C13 . 1.388(4) no
 C13 C14 . 1.387(4) no