#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:19:39 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178381 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/03/4020324.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_4020324
loop_
_publ_author_name
'Fabian Mohr'
'Seth A. Binfield'
'James C. Fettinger'
'Andrei N. Vedernikov'
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4833
_journal_page_last               4839
_journal_paper_doi               10.1021/jo050485f
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C23 H20 Cl6 Cu2 N4'
_chemical_formula_weight         692.21
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 105.510(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6293(15)
_cell_length_b                   13.7395(18)
_cell_length_c                   16.846(2)
_cell_measurement_temperature    173(2)
_cell_volume                     2593.6(6)
_diffrn_ambient_temperature      173(2)
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_meas      0
_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 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4020324
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Cu1 Cu 0.57875(4) 0.17842(3) 0.07255(2) 0.02811(13) Uani 1 1 d . . .
Cl1 Cl 0.74505(8) 0.38443(6) 0.11027(5) 0.0378(2) Uani 1 1 d . . .
N1 N 0.6698(2) 0.25330(18) -0.00429(15) 0.0233(6) Uani 1 1 d . . .
C1 C 0.7273(3) 0.3376(2) 0.0117(2) 0.0261(7) Uani 1 1 d . . .
C2 C 0.7745(3) 0.3889(2) -0.0425(2) 0.0307(8) Uani 1 1 d . . .
H2 H 0.815(3) 0.447(3) -0.028(2) 0.039(10) Uiso 1 1 d . . .
C3 C 0.7590(3) 0.3496(3) -0.1202(2) 0.0324(8) Uani 1 1 d . . .
H3 H 0.786(3) 0.382(3) -0.156(2) 0.038(11) Uiso 1 1 d . . .
C4 C 0.7006(3) 0.2620(2) -0.1390(2) 0.0291(7) Uani 1 1 d . . .
H4 H 0.691(3) 0.233(2) -0.190(2) 0.031(9) Uiso 1 1 d . . .
C5 C 0.6587(3) 0.2146(2) -0.08011(19) 0.0232(7) Uani 1 1 d . . .
C6 C 0.5999(3) 0.1158(2) -0.0952(2) 0.0273(7) Uani 1 1 d . . .
H6A H 0.610(3) 0.093(2) -0.146(2) 0.023(8) Uiso 1 1 d . . .
H6B H 0.637(3) 0.073(3) -0.052(2) 0.031(9) Uiso 1 1 d . . .
C7 C 0.4704(3) 0.1185(2) -0.09565(19) 0.0239(7) Uani 1 1 d . . .
N7 N 0.4476(2) 0.13142(19) -0.02156(16) 0.0256(6) Uani 1 1 d . . .
C8 C 0.3798(3) 0.1103(2) -0.1679(2) 0.0292(8) Uani 1 1 d . . .
H8 H 0.398(3) 0.104(2) -0.219(2) 0.028(9) Uiso 1 1 d . . .
C9 C 0.2623(3) 0.1128(2) -0.1645(2) 0.0323(8) Uani 1 1 d . . .
H9 H 0.209(3) 0.109(2) -0.211(2) 0.027(9) Uiso 1 1 d . . .
C10 C 0.2384(3) 0.1242(3) -0.0892(2) 0.0327(8) Uani 1 1 d . . .
H10 H 0.167(3) 0.129(2) -0.087(2) 0.024(9) Uiso 1 1 d . . .
C11 C 0.3327(3) 0.1334(2) -0.0196(2) 0.0298(7) Uani 1 1 d . . .
H11 H 0.321(3) 0.144(2) 0.032(2) 0.017(8) Uiso 1 1 d . . .
C12 C 0.4435(3) 0.3495(2) 0.12986(19) 0.0260(7) Uani 1 1 d . . .
Cl12 Cl 0.43303(8) 0.39403(6) 0.03148(5) 0.0376(2) Uani 1 1 d . . .
N12 N 0.4962(2) 0.26334(18) 0.14839(15) 0.0235(6) Uani 1 1 d . . .
C13 C 0.3971(3) 0.4044(3) 0.1823(2) 0.0316(8) Uani 1 1 d . . .
H13 H 0.372(4) 0.461(3) 0.168(3) 0.052(12) Uiso 1 1 d . . .
C14 C 0.4070(3) 0.3692(3) 0.2599(2) 0.0305(8) Uani 1 1 d . . .
H14 H 0.380(3) 0.408(3) 0.297(2) 0.042(11) Uiso 1 1 d . . .
C15 C 0.4616(3) 0.2796(2) 0.2820(2) 0.0270(7) Uani 1 1 d . . .
H15 H 0.470(3) 0.254(2) 0.336(2) 0.030(9) Uiso 1 1 d . . .
C16 C 0.5045(3) 0.2286(2) 0.22529(18) 0.0222(7) Uani 1 1 d . . .
C17 C 0.5619(3) 0.1296(2) 0.2445(2) 0.0262(7) Uani 1 1 d . . .
H17A H 0.553(3) 0.111(2) 0.297(2) 0.020(8) Uiso 1 1 d . . .
H17B H 0.521(3) 0.083(2) 0.204(2) 0.024(8) Uiso 1 1 d . . .
C18 C 0.6904(3) 0.1272(2) 0.24280(19) 0.0246(7) Uani 1 1 d . . .
N18 N 0.7113(2) 0.13436(18) 0.16807(16) 0.0249(6) Uani 1 1 d . . .
C19 C 0.7829(3) 0.1194(2) 0.3139(2) 0.0294(7) Uani 1 1 d . . .
H19 H 0.767(3) 0.113(2) 0.3656(19) 0.017(8) Uiso 1 1 d . . .
C20 C 0.8996(3) 0.1164(3) 0.3083(2) 0.0350(8) Uani 1 1 d . . .
H20 H 0.959(3) 0.111(2) 0.352(2) 0.031(10) Uiso 1 1 d . . .
C21 C 0.9206(3) 0.1215(3) 0.2320(2) 0.0336(8) Uani 1 1 d . . .
H21 H 0.998(3) 0.121(2) 0.226(2) 0.026(9) Uiso 1 1 d . . .
C22 C 0.8241(3) 0.1314(2) 0.1634(2) 0.0302(8) Uani 1 1 d . . .
H22 H 0.836(3) 0.133(2) 0.111(2) 0.023(8) Uiso 1 1 d . . .
Cu31 Cu 0.40449(4) 0.54075(4) 0.43069(3) 0.04127(15) Uani 1 1 d . . .
Cl31 Cl 0.43796(8) 0.38183(6) 0.47977(5) 0.0324(2) Uani 1 1 d . . .
Cl32 Cl 0.26519(8) 0.59439(6) 0.32748(5) 0.0351(2) Uani 1 1 d . . .
C41 C 0.0722(4) 0.3172(3) 0.0910(3) 0.0445(10) Uani 1 1 d . . .
H41A H 0.126(4) 0.269(3) 0.116(3) 0.059(13) Uiso 1 1 d . . .
H41B H -0.002(3) 0.291(2) 0.074(2) 0.029(9) Uiso 1 1 d . . .
Cl41 Cl 0.08128(9) 0.41578(7) 0.16005(6) 0.0477(3) Uani 1 1 d . . .
Cl42 Cl 0.10839(12) 0.35328(9) 0.00060(8) 0.0646(3) Uani 1 1 d . . .
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
Cu1 N7 1.991(3) . ?
Cu1 N18 2.001(3) . ?
Cu1 N12 2.138(3) . ?
Cu1 N1 2.142(3) . ?
Cl1 C1 1.741(3) . ?
N1 C1 1.329(4) . ?
N1 C5 1.358(4) . ?
C1 C2 1.378(5) . ?
C2 C3 1.382(5) . ?
C2 H2 0.92(4) . ?
C3 C4 1.376(5) . ?
C3 H3 0.86(4) . ?
C4 C5 1.380(4) . ?
C4 H4 0.92(3) . ?
C5 C6 1.511(4) . ?
C6 C7 1.504(4) . ?
C6 H6A 0.94(3) . ?
C6 H6B 0.94(4) . ?
C7 N7 1.355(4) . ?
C7 C8 1.386(5) . ?
N7 C11 1.345(4) . ?
C8 C9 1.383(5) . ?
C8 H8 0.94(3) . ?
C9 C10 1.377(5) . ?
C9 H9 0.87(3) . ?
C10 C11 1.381(5) . ?
C10 H10 0.84(3) . ?
C11 H11 0.93(3) . ?
C12 N12 1.331(4) . ?
C12 C13 1.376(5) . ?
C12 Cl12 1.740(3) . ?
N12 C16 1.360(4) . ?
C13 C14 1.369(5) . ?
C13 H13 0.84(4) . ?
C14 C15 1.389(5) . ?
C14 H14 0.94(4) . ?
C15 C16 1.380(4) . ?
C15 H15 0.95(3) . ?
C16 C17 1.511(4) . ?
C17 C18 1.503(4) . ?
C17 H17A 0.94(3) . ?
C17 H17B 0.97(3) . ?
C18 N18 1.348(4) . ?
C18 C19 1.383(5) . ?
N18 C22 1.335(4) . ?
C19 C20 1.387(5) . ?
C19 H19 0.94(3) . ?
C20 C21 1.373(5) . ?
C20 H20 0.87(4) . ?
C21 C22 1.385(5) . ?
C21 H21 0.94(3) . ?
C22 H22 0.93(3) . ?
Cu31 Cl32 2.1644(10) . ?
Cu31 Cl31 2.2991(10) 3_666 ?
Cu31 Cl31 2.3303(10) . ?
Cu31 Cu31 2.9777(9) 3_666 ?
Cl31 Cu31 2.2991(10) 3_666 ?
C41 Cl42 1.757(5) . ?
C41 Cl41 1.770(4) . ?
C41 H41A 0.93(4) . ?
C41 H41B 0.90(4) . ?
