#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:59:05 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180406 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/75/7207527.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_7207527
loop_
_publ_author_name
'Gurskiy, Stanislav I.'
'Tafeenko, Viktor A.'
_publ_section_title
;
 The luminescent properties of structures built from
 3-cyano-4-dicyanomethylene-5-oxo-4,5-dihydro-1H-pyrrole-2-olate and
 copper(I,II) cations
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              2721
_journal_paper_doi               10.1039/c2ce06238k
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C16 H6 Cu N8 O6, 2(H2 O)'
_chemical_formula_sum            'C16 H10 Cu N8 O8'
_chemical_formula_weight         505.86
_chemical_melting_point          488
_chemical_name_systematic
;
Poly[[diaquabis(μ₂-3-cyano-4-dicyanomethylene-5-oxo-
4,5-dihydro-1H-pyrrol-2-olato-κ²N³:N^3'^)copper(II)] dihydrate]
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 125.406(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.9657(19)
_cell_length_b                   10.8842(11)
_cell_length_c                   11.7477(12)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      40
_cell_measurement_theta_min      32
_cell_volume                     1976.6(5)
_computing_cell_refinement       'CAD-4 Software (Enraf-Nonius, 1989'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989'
_computing_data_reduction        'XCAD-4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2000; '
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4 diffractometr'
_diffrn_measurement_method       'non-profiled omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2057
_diffrn_reflns_theta_full        72.92
_diffrn_reflns_theta_max         72.92
_diffrn_reflns_theta_min         4.97
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.172
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'black red'
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1020
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       0.00182(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0372
_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)+(0.0631P)²+1.8621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1054
_reflns_number_gt                1780
_reflns_number_total             1962
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce06238k.txt
_cod_data_source_block           red
_cod_original_cell_volume        1976.6(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7207527
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_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
Cu1 Cu 0.2500 0.7500 0.0000 0.02693(19) Uani 1 2 d S
O1 O 0.05963(14) 1.36056(18) -0.33947(19) 0.0525(5) Uani 1 1 d .
O2 O 0.18774(14) 1.39450(16) 0.12737(19) 0.0528(5) Uani 1 1 d .
N1 N 0.12401(15) 1.41051(19) -0.1088(2) 0.0393(5) Uani 1 1 d .
N2 N 0.06556(17) 1.0196(2) -0.3212(2) 0.0540(6) Uani 1 1 d .
N3 N 0.20417(13) 0.90500(17) 0.02996(19) 0.0346(4) Uani 1 1 d .
N4 N 0.23713(14) 1.17796(16) 0.33463(19) 0.0349(4) Uani 1 1 d .
C2 C 0.09554(16) 1.3305(2) -0.2184(2) 0.0370(5) Uani 1 1 d .
C3 C 0.11542(15) 1.2058(2) -0.1594(2) 0.0326(5) Uani 1 1 d .
C4 C 0.15368(15) 1.21364(19) -0.0183(2) 0.0292(4) Uani 1 1 d .
C5 C 0.15825(15) 1.34994(19) 0.0147(2) 0.0344(5) Uani 1 1 d .
C6 C 0.08982(16) 1.1016(2) -0.2466(2) 0.0370(5) Uani 1 1 d .
C7 C 0.18701(15) 1.12452(19) 0.0867(2) 0.0294(4) Uani 1 1 d .
C8 C 0.19560(14) 1.00122(19) 0.0582(2) 0.0291(4) Uani 1 1 d .
C9 C 0.21531(15) 1.15460(18) 0.2241(2) 0.0303(5) Uani 1 1 d .
O3 O 0.38889(12) 0.82916(15) 0.14329(18) 0.0369(4) Uani 1 1 d .
O4 O 0.50224(16) 0.7363(2) 0.0875(2) 0.0499(5) Uani 1 1 d .
H1 H 0.114(2) 1.483(4) -0.122(4) 0.063(10) Uiso 1 1 d .
H3 H 0.413(2) 0.808(4) 0.224(4) 0.064(10) Uiso 1 1 d .
H31 H 0.418(2) 0.795(4) 0.119(4) 0.070(11) Uiso 1 1 d .
H4 H 0.490(3) 0.764(3) 0.030(4) 0.056(12) Uiso 1 1 d .
H41 H 0.513(4) 0.674(5) 0.100(6) 0.11(2) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N4 Cu1 N4 180.00(9) 4_545 6_575
N4 Cu1 N3 88.89(7) 4_545 .
N4 Cu1 N3 91.11(7) 6_575 .
N4 Cu1 N3 91.11(7) 4_545 7_565
N4 Cu1 N3 88.89(7) 6_575 7_565
N3 Cu1 N3 180.0 . 7_565
N4 Cu1 O3 90.43(8) 4_545 7_565
N4 Cu1 O3 89.57(8) 6_575 7_565
N3 Cu1 O3 90.82(7) . 7_565
N3 Cu1 O3 89.18(7) 7_565 7_565
N4 Cu1 O3 89.57(8) 4_545 .
N4 Cu1 O3 90.43(8) 6_575 .
N3 Cu1 O3 89.18(7) . .
N3 Cu1 O3 90.82(7) 7_565 .
O3 Cu1 O3 180.0 7_565 .
C5 N1 C2 111.99(19) . .
C5 N1 H1 126(3) . .
C2 N1 H1 121(3) . .
C8 N3 Cu1 165.4(2) . .
C9 N4 Cu1 164.94(19) . 4
O1 C2 N1 125.1(2) . .
O1 C2 C3 128.1(2) . .
N1 C2 C3 106.73(19) . .
C4 C3 C6 130.1(2) . .
C4 C3 C2 108.9(2) . .
C6 C3 C2 120.9(2) . .
C3 C4 C7 132.3(2) . .
C3 C4 C5 106.24(19) . .
C7 C4 C5 121.40(19) . .
O2 C5 N1 127.3(2) . .
O2 C5 C4 126.5(2) . .
N1 C5 C4 106.15(19) . .
N2 C6 C3 176.9(3) . .
C4 C7 C9 121.65(19) . .
C4 C7 C8 120.27(18) . .
C9 C7 C8 118.05(19) . .
N3 C8 C7 175.5(2) . .
N4 C9 C7 179.0(3) . .
Cu1 O3 H3 112(3) . .
Cu1 O3 H31 106(3) . .
H3 O3 H31 103(4) . .
H4 O4 H41 124(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N4 1.9746(17) 4_545
Cu1 N4 1.9746(17) 6_575
Cu1 N3 2.0199(18) .
Cu1 N3 2.0199(18) 7_565
Cu1 O3 2.3188(18) 7_565
Cu1 O3 2.3188(18) .
O1 C2 1.213(3) .
O2 C5 1.201(3) .
N1 C5 1.366(3) .
N1 C2 1.379(3) .
N1 H1 0.80(4) .
N2 C6 1.144(3) .
N3 C8 1.138(3) .
N4 C9 1.140(3) .
N4 Cu1 1.9746(17) 4
C2 C3 1.470(3) .
C3 C4 1.374(3) .
C3 C6 1.413(3) .
C4 C7 1.399(3) .
C4 C5 1.523(3) .
C7 C9 1.414(3) .
C7 C8 1.415(3) .
O3 H3 0.81(4) .
O3 H31 0.84(4) .
O4 H4 0.65(4) .
O4 H41 0.71(5) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H31 O4 0.84(4) 1.95(4) 2.776(3) 169(4) .
O3 H3 O4 0.81(4) 1.99(4) 2.779(3) 163(4) 2_655
O4 H4 O1 0.65(4) 2.13(4) 2.781(3) 175(5) 4_544
O4 H41 N2 0.71(5) 2.28(5) 2.976(4) 170(6) 8_566
N1 H1 O3 0.80(4) 2.06(4) 2.853(3) 170(3) 7_575
