#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/01/4020177.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4020177
loop_
_publ_author_name
'Fu-Lu Zhao'
'Jin-Tao Liu'
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3801
_journal_page_last               3805
_journal_paper_doi               10.1021/jo0477852
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C13 H13 Cl2 F2 N O4'
_chemical_formula_weight         356.14
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                109.281(3)
_cell_angle_beta                 97.029(3)
_cell_angle_gamma                107.275(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9132(12)
_cell_length_b                   9.9342(16)
_cell_length_c                   10.9874(18)
_cell_measurement_temperature    293(2)
_cell_volume                     754.9(2)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.567
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_formula_sum        'C13 H13 N O4 F2 Cl2'
_cod_database_code               4020177
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.5390(3) 0.3670(2) 0.2867(2) 0.1155(8) Uani 1 1 d . . .
Cl2 Cl 0.1935(2) 0.98876(17) 0.07521(13) 0.0837(6) Uani 1 1 d . . .
F1 F 0.5517(5) 0.6215(3) 0.4391(3) 0.0923(11) Uani 1 1 d . . .
F2 F 0.3903(3) 0.5200(4) 0.2284(3) 0.0858(10) Uani 1 1 d . . .
N1 N 0.7421(4) 0.7932(3) 0.3073(3) 0.0473(8) Uani 1 1 d . . .
H13 H 0.8378 0.8663 0.3626 0.057 Uiso 1 1 calc R . .
O1 O 0.7225(4) 0.5558(3) 0.1508(2) 0.0488(7) Uani 1 1 d . . .
O2 O 1.0331(5) 0.6072(5) 0.1824(3) 0.0787(11) Uani 1 1 d . . .
O3 O 0.9554(6) 0.8734(4) 0.5631(3) 0.0818(12) Uani 1 1 d . . .
O4 O 0.9846(5) 0.6722(4) 0.5933(3) 0.0718(10) Uani 1 1 d . . .
C1 C 0.7342(5) 0.6415(4) 0.2841(3) 0.0413(8) Uani 1 1 d . . .
C2 C 0.9061(6) 0.6468(5) 0.3726(4) 0.0516(10) Uani 1 1 d . . .
H1 H 0.8895 0.5420 0.3641 0.062 Uiso 1 1 calc R . .
C3 C 1.0682(6) 0.7024(7) 0.3156(5) 0.0727(14) Uani 1 1 d . . .
H3 H 1.0883 0.8063 0.3231 0.087 Uiso 1 1 calc R . .
H2 H 1.1776 0.7019 0.3658 0.087 Uiso 1 1 calc R . .
C4 C 0.8806(6) 0.6136(6) 0.1089(4) 0.0647(12) Uani 1 1 d . . .
H4 H 0.8628 0.5543 0.0153 0.078 Uiso 1 1 calc R . .
H5 H 0.9011 0.7187 0.1201 0.078 Uiso 1 1 calc R . .
C5 C 0.5598(7) 0.5475(5) 0.3104(5) 0.0669(13) Uani 1 1 d . . .
C6 C 0.9472(6) 0.7439(5) 0.5178(4) 0.0535(10) Uani 1 1 d . . .
C7 C 1.0337(9) 0.7571(7) 0.7335(5) 0.0841(17) Uani 1 1 d . . .
H8 H 1.1526 0.8349 0.7586 0.126 Uiso 1 1 calc R . .
H7 H 1.0355 0.6897 0.7788 0.126 Uiso 1 1 calc R . .
H6 H 0.9462 0.8040 0.7575 0.126 Uiso 1 1 calc R . .
C8 C 0.6100(5) 0.8348(4) 0.2492(4) 0.0432(8) Uani 1 1 d . . .
C9 C 0.5286(7) 0.7701(5) 0.1147(4) 0.0602(12) Uani 1 1 d . . .
H9 H 0.5610 0.6937 0.0588 0.072 Uiso 1 1 calc R . .
C10 C 0.4000(7) 0.8168(6) 0.0617(4) 0.0651(12) Uani 1 1 d . . .
H10 H 0.3435 0.7701 -0.0287 0.078 Uiso 1 1 calc R . .
C11 C 0.3565(6) 0.9323(5) 0.1431(4) 0.0546(10) Uani 1 1 d . . .
C12 C 0.4384(6) 1.0011(5) 0.2769(4) 0.0569(10) Uani 1 1 d . . .
H11 H 0.4091 1.0803 0.3317 0.068 Uiso 1 1 calc R . .
C13 C 0.5629(6) 0.9523(5) 0.3284(4) 0.0523(10) Uani 1 1 d . . .
H12 H 0.6178 0.9989 0.4190 0.063 Uiso 1 1 calc R . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.678(5) . ?
Cl2 C11 1.734(4) . ?
F1 C5 1.381(5) . ?
F2 C5 1.418(6) . ?
N1 C8 1.392(5) . ?
N1 C1 1.424(4) . ?
N1 H13 0.8600 . ?
O1 C1 1.406(4) . ?
O1 C4 1.412(5) . ?
O2 C3 1.395(6) . ?
O2 C4 1.398(6) . ?
O3 C6 1.194(5) . ?
O4 C6 1.319(5) . ?
O4 C7 1.427(5) . ?
C1 C5 1.539(6) . ?
C1 C2 1.548(5) . ?
C2 C6 1.501(5) . ?
C2 C3 1.532(7) . ?
C2 H1 0.9800 . ?
C3 H3 0.9700 . ?
C3 H2 0.9700 . ?
C4 H4 0.9700 . ?
C4 H5 0.9700 . ?
C7 H8 0.9600 . ?
C7 H7 0.9600 . ?
C7 H6 0.9600 . ?
C8 C9 1.381(5) . ?
C8 C13 1.388(5) . ?
C9 C10 1.379(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(6) . ?
C12 C13 1.362(6) . ?
C12 H11 0.9300 . ?
C13 H12 0.9300 . ?
