#------------------------------------------------------------------------------
#$Date: 2011-03-31 12:48:06 +0100 (Thu, 31 Mar 2011) $
#$Revision: 17004 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202523.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_2202523
loop_
_publ_author_name
'Xue-Mei Li'
'Hua-You Hu'
'Jian-Hua Xu'
'Shu-Sheng Zhang'
'Hoong-Kun Fun'
_publ_section_title
;
2a,5a-Dichloro-4-methyl-1-methylene-2-phenyl-2a,5a-dihydrocyclobuta[c]pyrrole-
3,5-dione
;
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o1822
_journal_page_last               o1823
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C14 H11 Cl2 N O2'
_chemical_formula_moiety         'C14 H11 Cl2 N O2'
_chemical_formula_sum            'C14 H11 Cl2 N O2'
_chemical_formula_weight         296.14
_chemical_melting_point          407.5(5)
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 106.1670(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.8302(11)
_cell_length_b                   7.3973(5)
_cell_length_c                   25.3885(18)
_cell_measurement_temperature    293(2)
_cell_volume                     2675.1(3)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.471
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_chemical_melting_point' value '407-408 K' was changed to '407.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               2202523
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
Cl1 -0.01248(4) 0.95649(9) 0.07205(3) 0.0386(2) Uani d . 1 . . Cl
Cl2 0.10127(6) 0.92538(11) 0.20482(3) 0.0495(2) Uani d . 1 . . Cl
O1 0.09626(15) 0.6853(3) 0.01726(8) 0.0524(6) Uani d . 1 . . O
O2 0.27917(15) 0.7240(3) 0.19346(9) 0.0571(6) Uani d . 1 . . O
N1 0.20372(15) 0.6917(3) 0.10169(10) 0.0355(5) Uani d . 1 . . N
C1 0.11558(18) 0.7078(4) 0.06601(11) 0.0333(6) Uani d . 1 . . C
C2 0.04696(17) 0.7578(3) 0.09887(10) 0.0277(5) Uani d . 1 . . C
C3 0.10893(18) 0.7510(4) 0.15935(10) 0.0314(6) Uani d . 1 . . C
C4 0.20898(19) 0.7243(4) 0.15627(12) 0.0368(6) Uani d . 1 . . C
C5 0.2864(2) 0.6441(4) 0.08401(15) 0.0481(8) Uani d . 1 . . C
H5A 0.2889 0.7187 0.0535 0.072 Uiso calc R 1 . . H
H5B 0.2827 0.5194 0.0732 0.072 Uiso calc R 1 . . H
H5C 0.3420 0.6631 0.1137 0.072 Uiso calc R 1 . . H
C6 0.06019(18) 0.5739(4) 0.16548(11) 0.0338(6) Uani d . 1 . . C
C7 -0.01225(19) 0.5920(4) 0.10977(11) 0.0314(6) Uani d . 1 . . C
C8 -0.11163(18) 0.6327(3) 0.11099(11) 0.0303(5) Uani d . 1 . . C
C9 -0.1848(2) 0.6099(4) 0.06379(12) 0.0390(7) Uani d . 1 . . C
C10 -0.2768(2) 0.6453(5) 0.06369(14) 0.0457(8) Uani d . 1 . . C
C11 -0.2962(2) 0.7040(4) 0.11067(14) 0.0452(7) Uani d . 1 . . C
C12 -0.2244(2) 0.7273(5) 0.15780(14) 0.0456(7) Uani d . 1 . . C
C13 -0.1328(2) 0.6916(4) 0.15785(12) 0.0405(7) Uani d . 1 . . C
C14 0.0794(3) 0.4499(5) 0.20380(15) 0.0510(8) Uani d . 1 . . C
H14B 0.040(3) 0.344(5) 0.1978(14) 0.059(10) Uiso d . 1 . . H
H13 -0.085(2) 0.708(4) 0.1898(12) 0.038(8) Uiso d . 1 . . H
H7 -0.0099(18) 0.497(4) 0.0871(11) 0.027(7) Uiso d . 1 . . H
H9 -0.172(2) 0.568(5) 0.0330(14) 0.051(9) Uiso d . 1 . . H
H10 -0.320(2) 0.625(5) 0.0327(15) 0.062(11) Uiso d . 1 . . H
H11 -0.358(2) 0.736(4) 0.1114(12) 0.045(9) Uiso d . 1 . . H
H12 -0.237(2) 0.768(5) 0.1862(14) 0.053(10) Uiso d . 1 . . H
H14A 0.132(2) 0.466(5) 0.2363(15) 0.055(10) Uiso d . 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
Cl1 0.0284(3) 0.0391(4) 0.0477(4) 0.0070(3) 0.0093(3) 0.0131(3)
Cl2 0.0708(5) 0.0432(4) 0.0358(4) 0.0038(4) 0.0172(3) -0.0105(3)
O1 0.0493(12) 0.0805(17) 0.0320(11) 0.0001(12) 0.0193(9) -0.0085(11)
O2 0.0337(11) 0.0698(16) 0.0558(14) -0.0002(11) -0.0074(10) -0.0026(12)
N1 0.0267(11) 0.0378(13) 0.0436(13) 0.0043(9) 0.0123(9) -0.0009(10)
C1 0.0311(13) 0.0367(15) 0.0356(15) 0.0013(11) 0.0153(11) -0.0015(12)
C2 0.0260(12) 0.0312(13) 0.0259(12) 0.0064(10) 0.0076(9) 0.0004(10)
C3 0.0342(13) 0.0334(14) 0.0253(12) 0.0054(11) 0.0063(10) -0.0037(11)
C4 0.0318(14) 0.0325(14) 0.0436(16) 0.0012(11) 0.0061(12) 0.0008(12)
C5 0.0324(14) 0.0426(17) 0.077(2) 0.0069(13) 0.0285(15) 0.0027(16)
C6 0.0339(13) 0.0368(15) 0.0326(14) 0.0085(11) 0.0123(11) 0.0032(11)
C7 0.0368(14) 0.0272(13) 0.0333(14) 0.0016(11) 0.0147(11) -0.0036(11)
C8 0.0328(13) 0.0261(13) 0.0333(14) -0.0042(10) 0.0117(11) 0.0008(10)
C9 0.0443(16) 0.0396(16) 0.0329(15) -0.0038(13) 0.0105(12) -0.0050(12)
C10 0.0315(15) 0.0517(19) 0.0467(18) -0.0085(13) -0.0012(13) -0.0013(15)
C11 0.0333(15) 0.0456(18) 0.059(2) -0.0035(13) 0.0169(14) 0.0005(15)
C12 0.0416(16) 0.055(2) 0.0451(18) 0.0004(14) 0.0204(14) -0.0040(15)
C13 0.0329(14) 0.0560(19) 0.0328(15) -0.0022(13) 0.0096(12) -0.0051(13)
C14 0.058(2) 0.046(2) 0.0484(19) 0.0125(17) 0.0140(16) 0.0129(16)
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
Cl1 C2 . 1.751(3) y
Cl2 C3 . 1.756(3) y
O1 C1 . 1.202(3) y
O2 C4 . 1.195(3) y
N1 C1 . 1.373(3) y
N1 C4 . 1.387(4) y
N1 C5 . 1.462(3) y
C1 C2 . 1.530(4) yes
C2 C3 . 1.555(3) yes
C2 C7 . 1.577(4) yes
C3 C4 . 1.520(4) yes
C3 C6 . 1.525(4) yes
C5 H5A . 0.96 ?
C5 H5B . 0.96 ?
C5 H5C . 0.96 ?
C6 C14 . 1.309(4) y
C6 C7 . 1.525(4) y
C7 C8 . 1.513(4) y
C7 H7 . 0.92(3) ?
C8 C13 . 1.383(4) ?
C8 C9 . 1.385(4) ?
C9 C10 . 1.388(4) ?
C9 H9 . 0.91(4) ?
C10 C11 . 1.373(5) ?
C10 H10 . 0.88(3) ?
C11 C12 . 1.373(4) ?
C11 H11 . 0.94(3) ?
C12 C13 . 1.383(4) ?
C12 H12 . 0.85(4) ?
C13 H13 . 0.93(3) ?
C14 H14B . 0.96(4) ?
C14 H14A . 0.97(4) ?