#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/05/2220520.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2220520
loop_
_publ_author_name
'Li, Bai-Yu'
'Tong, Jun-Feng'
'Dong, Wen-Kui'
'Yao, Jian'
'Wu, Jian-Chao'
_publ_section_title
Bis(N,N-dimethylformamide-κO)bis(2,4,6-trinitrophenolato-κ²O¹,O²)copper(II)
_journal_coeditor_code           HG2446
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1
_journal_paper_doi               10.1107/S1600536808039846
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu (C6 H2 N3 O7)2 (C3 H7 N O)2]'
_chemical_formula_moiety         'C18 H18 Cu N8 O16'
_chemical_formula_sum            'C18 H18 Cu N8 O16'
_chemical_formula_weight         665.94
_chemical_name_systematic
;Bis(N,N-dimethylformamide-κO)bis(2,4,6-trinitrophenolato-
κ²O¹,O²)copper(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.9450(10)
_cell_angle_beta                 88.796(2)
_cell_angle_gamma                87.968(2)
_cell_formula_units_Z            1
_cell_length_a                   8.0620(10)
_cell_length_b                   8.3361(11)
_cell_length_c                   9.8429(14)
_cell_measurement_reflns_used    2174
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.446
_cell_measurement_theta_min      2.544
_cell_volume                     635.25(15)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3320
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.956
_exptl_absorpt_correction_T_max  0.7624
_exptl_absorpt_correction_T_min  0.6728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block-like
_exptl_crystal_F_000             339
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.361
_refine_ls_extinction_coef       0.141(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.036P)²+0.273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                1973
_reflns_number_total             2198
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2446.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2220520
_cod_database_fobs_code          2220520
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cu Cu1 0.5000 0.5000 0.5000 0.02554(17) Uani d S 1 . .
N N1 0.5597(3) 0.5206(2) 0.1667(2) 0.0339(5) Uani d . 1 . .
N N2 0.8515(3) 1.0013(3) -0.1186(2) 0.0407(5) Uani d . 1 . .
N N3 0.5610(3) 1.0497(2) 0.3079(2) 0.0341(5) Uani d . 1 . .
N N4 0.9697(2) 0.3374(2) 0.4240(2) 0.0289(4) Uani d . 1 . .
O O1 0.4863(2) 0.71913(19) 0.36927(16) 0.0332(4) Uani d . 1 . .
O O2 0.4407(2) 0.4683(2) 0.2441(2) 0.0497(5) Uani d . 1 . .
O O3 0.6381(3) 0.4363(2) 0.1017(2) 0.0496(5) Uani d . 1 . .
O O4 0.9214(3) 0.9088(3) -0.1814(2) 0.0587(6) Uani d . 1 . .
O O5 0.8672(3) 1.1525(3) -0.1527(2) 0.0639(6) Uani d . 1 . .
O O6 0.6713(3) 1.1133(3) 0.3553(2) 0.0552(5) Uani d . 1 . .
O O7 0.4137(3) 1.0653(2) 0.3315(2) 0.0556(5) Uani d . 1 . .
O O8 0.72371(18) 0.47226(19) 0.43167(16) 0.0306(4) Uani d . 1 . .
C C1 0.5606(3) 0.7778(3) 0.2512(2) 0.0255(5) Uani d . 1 . .
C C2 0.6088(3) 0.6916(3) 0.1486(2) 0.0265(5) Uani d . 1 . .
C C3 0.7030(3) 0.7633(3) 0.0293(2) 0.0301(5) Uani d . 1 . .
H H3 0.7350 0.7018 -0.0331 0.036 Uiso calc R 1 . .
C C4 0.7490(3) 0.9268(3) 0.0041(2) 0.0298(5) Uani d . 1 . .
C C5 0.7014(3) 1.0223(3) 0.0951(2) 0.0287(5) Uani d . 1 . .
H H5 0.7312 1.1331 0.0767 0.034 Uiso calc R 1 . .
C C6 0.6098(3) 0.9480(3) 0.2118(2) 0.0259(5) Uani d . 1 . .
C C7 0.8263(3) 0.3548(3) 0.4840(2) 0.0278(5) Uani d . 1 . .
H H7 0.7989 0.2774 0.5687 0.033 Uiso calc R 1 . .
C C8 1.0134(3) 0.4484(4) 0.2868(3) 0.0434(6) Uani d . 1 . .
H H8A 0.9757 0.4034 0.2134 0.065 Uiso calc R 1 . .
H H8B 1.1317 0.4587 0.2795 0.065 Uiso calc R 1 . .
H H8C 0.9615 0.5564 0.2768 0.065 Uiso calc R 1 . .
C C9 1.0878(3) 0.2028(3) 0.4895(3) 0.0402(6) Uani d . 1 . .
H H9A 1.0476 0.1441 0.5817 0.060 Uiso calc R 1 . .
H H9B 1.1933 0.2489 0.4979 0.060 Uiso calc R 1 . .
H H9C 1.1001 0.1270 0.4320 0.060 Uiso calc R 1 . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O1 Cu1 O1 2_666 . 180.0 ?
O1 Cu1 O8 2_666 . 90.87(6) ?
O1 Cu1 O8 . . 89.13(6) ?
O1 Cu1 O8 2_666 2_666 89.13(6) ?
O1 Cu1 O8 . 2_666 90.87(6) ?
O8 Cu1 O8 . 2_666 180.0000(10) ?
O1 Cu1 O2 2_666 . 108.49(7) ?
O1 Cu1 O2 . . 71.51(7) ?
O8 Cu1 O2 . . 78.81(6) ?
O8 Cu1 O2 2_666 . 101.19(6) ?
O3 N1 O2 . . 123.1(2) ?
O3 N1 C2 . . 118.1(2) ?
O2 N1 C2 . . 118.8(2) ?
O5 N2 O4 . . 123.1(2) ?
O5 N2 C4 . . 118.4(2) ?
O4 N2 C4 . . 118.5(2) ?
O6 N3 O7 . . 125.3(2) ?
O6 N3 C6 . . 117.4(2) ?
O7 N3 C6 . . 117.3(2) ?
C7 N4 C8 . . 120.7(2) ?
C7 N4 C9 . . 121.3(2) ?
C8 N4 C9 . . 117.95(19) ?
C1 O1 Cu1 . . 130.29(14) ?
N1 O2 Cu1 . . 108.53(14) ?
C7 O8 Cu1 . . 126.60(14) ?
O1 C1 C6 . . 119.4(2) ?
O1 C1 C2 . . 127.7(2) ?
C6 C1 C2 . . 112.79(19) ?
C3 C2 C1 . . 123.0(2) ?
C3 C2 N1 . . 116.6(2) ?
C1 C2 N1 . . 120.38(19) ?
C4 C3 C2 . . 119.3(2) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C3 C4 C5 . . 121.5(2) ?
C3 C4 N2 . . 119.6(2) ?
C5 C4 N2 . . 118.9(2) ?
C6 C5 C4 . . 117.8(2) ?
C6 C5 H5 . . 121.1 ?
C4 C5 H5 . . 121.1 ?
C5 C6 C1 . . 125.5(2) ?
C5 C6 N3 . . 117.3(2) ?
C1 C6 N3 . . 117.15(18) ?
O8 C7 N4 . . 122.7(2) ?
O8 C7 H7 . . 118.7 ?
N4 C7 H7 . . 118.7 ?
N4 C8 H8A . . 109.5 ?
N4 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
N4 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N4 C9 H9A . . 109.5 ?
N4 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
N4 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
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
Cu1 O1 2_666 1.9226(15) ?
Cu1 O1 . 1.9226(15) ?
Cu1 O8 . 1.9401(15) ?
Cu1 O8 2_666 1.9401(15) ?
Cu1 O2 . 2.659(2) ?
N1 O3 . 1.226(3) ?
N1 O2 . 1.228(3) ?
N1 C2 . 1.455(3) ?
N2 O5 . 1.222(3) ?
N2 O4 . 1.230(3) ?
N2 C4 . 1.452(3) ?
N3 O6 . 1.215(3) ?
N3 O7 . 1.215(3) ?
N3 C6 . 1.474(3) ?
N4 C7 . 1.310(3) ?
N4 C8 . 1.455(3) ?
N4 C9 . 1.459(3) ?
O1 C1 . 1.275(3) ?
O8 C7 . 1.261(3) ?
C1 C6 . 1.431(3) ?
C1 C2 . 1.432(3) ?
C2 C3 . 1.385(3) ?
C3 C4 . 1.379(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.393(3) ?
C5 C6 . 1.361(3) ?
C5 H5 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
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
O8 Cu1 O1 C1 . . . . 27.0(2) ?
O8 Cu1 O1 C1 2_666 . . . -153.0(2) ?
O2 Cu1 O1 C1 . . . . -51.52(19) ?
O3 N1 O2 Cu1 . . . . 123.9(2) ?
C2 N1 O2 Cu1 . . . . -57.3(2) ?
O1 Cu1 O2 N1 2_666 . . . -115.98(15) ?
O1 Cu1 O2 N1 . . . . 64.02(15) ?
O8 Cu1 O2 N1 . . . . -28.83(15) ?
O8 Cu1 O2 N1 2_666 . . . 151.17(15) ?
O1 Cu1 O8 C7 2_666 . . . -8.81(18) ?
O1 Cu1 O8 C7 . . . . 171.19(18) ?
O2 Cu1 O8 C7 . . . . -117.49(19) ?
Cu1 O1 C1 C6 . . . . -144.15(17) ?
Cu1 O1 C1 C2 . . . . 33.8(3) ?
O1 C1 C2 C3 . . . . -173.8(2) ?
C6 C1 C2 C3 . . . . 4.3(3) ?
O1 C1 C2 N1 . . . . 5.9(3) ?
C6 C1 C2 N1 . . . . -176.03(19) ?
O3 N1 C2 C3 . . . . 19.5(3) ?
O2 N1 C2 C3 . . . . -159.3(2) ?
O3 N1 C2 C1 . . . . -160.2(2) ?
O2 N1 C2 C1 . . . . 21.0(3) ?
C1 C2 C3 C4 . . . . -2.2(3) ?
N1 C2 C3 C4 . . . . 178.0(2) ?
C2 C3 C4 C5 . . . . -0.7(3) ?
C2 C3 C4 N2 . . . . 178.4(2) ?
O5 N2 C4 C3 . . . . 167.6(2) ?
O4 N2 C4 C3 . . . . -14.0(3) ?
O5 N2 C4 C5 . . . . -13.3(3) ?
O4 N2 C4 C5 . . . . 165.1(2) ?
C3 C4 C5 C6 . . . . 1.1(3) ?
N2 C4 C5 C6 . . . . -177.9(2) ?
C4 C5 C6 C1 . . . . 1.4(3) ?
C4 C5 C6 N3 . . . . 179.6(2) ?
O1 C1 C6 C5 . . . . 174.3(2) ?
C2 C1 C6 C5 . . . . -3.9(3) ?
O1 C1 C6 N3 . . . . -3.9(3) ?
C2 C1 C6 N3 . . . . 177.93(19) ?
O6 N3 C6 C5 . . . . -56.1(3) ?
O7 N3 C6 C5 . . . . 122.8(2) ?
O6 N3 C6 C1 . . . . 122.2(2) ?
O7 N3 C6 C1 . . . . -58.9(3) ?
Cu1 O8 C7 N4 . . . . 173.74(16) ?
C8 N4 C7 O8 . . . . -4.3(3) ?
C9 N4 C7 O8 . . . . 178.2(2) ?
