#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/69/2016953.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_2016953
loop_
_publ_author_name
'Tafeenko, Viktor A.'
'Gurskiy, Stanislav I.'
'Baranov, Andrey N.'
'Kaisarova, Tatiana V.'
'Aslanov, Leonid A.'
_publ_section_title
;
 Luminescence properties of three structures built from
 3-cyano-4-dicyanomethylene-5-oxo-4,5-dihydro-1H-pyrrol-2-olate
 and alkaline metals (Na, K and Rb)
;
_journal_coeditor_code           FA3172
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m52
_journal_page_last               m55
_journal_paper_doi               10.1107/S0108270108043783
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'Na +, C8 H N4 O2 -, 2H2 O'
_chemical_formula_moiety         'Na +, C8 H N4 O2 -, 2(H2 O)'
_chemical_formula_sum            'C8 H5 N4 Na O4'
_chemical_formula_weight         244.15
_chemical_melting_point          530
_chemical_name_systematic
;sodium(I)
3-cyano-4-dicyanomethylene-5-oxo-4,5-dihydro-1H-pyrrol-2-olate
 dihydrate
;
_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                108.849(12)
_cell_angle_beta                 94.079(12)
_cell_angle_gamma                91.58(2)
_cell_formula_units_Z            2
_cell_length_a                   3.6549(8)
_cell_length_b                   10.1920(12)
_cell_length_c                   14.8401(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      46
_cell_measurement_theta_min      31
_cell_volume                     521.09(15)
_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  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_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  0.0769
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1794
_diffrn_reflns_theta_full        64.90
_diffrn_reflns_theta_max         64.90
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.447
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.242
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         1721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0523
_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)+(0.0793P)²+0.0504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                1212
_reflns_number_total             1721
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            fa3172.cif
_cod_data_source_block           na
_cod_original_cell_volume        521.09(14)
_cod_database_code               2016953
_cod_database_fobs_code          2016953
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
Na Na1 0.5000 0.0000 0.0000 0.0481(6) Uani d S 1 . .
Na Na2 0.5000 1.0000 0.5000 0.0476(6) Uani d S 1 . .
O O2 0.4265(7) 0.7657(2) 0.39509(16) 0.0442(6) Uani d . 1 . .
O O1 0.1066(6) 0.3364(2) 0.40524(15) 0.0393(6) Uani d . 1 . .
O O3 1.0052(8) -0.1169(3) 0.0466(2) 0.0507(7) Uani d . 1 . .
O O4 0.0070(8) 0.9473(3) 0.5946(2) 0.0524(7) Uani d . 1 . .
N N1 0.2217(7) 0.5660(3) 0.42007(18) 0.0341(6) Uani d . 1 . .
N N2 0.7957(10) 0.3975(3) 0.0521(2) 0.0574(9) Uani d . 1 . .
N N3 0.7784(11) 0.8305(4) 0.2227(2) 0.0604(10) Uani d . 1 . .
N N4 0.4828(10) 0.1678(3) 0.1643(2) 0.0565(9) Uani d . 1 . .
C C2 0.2217(9) 0.4240(3) 0.3718(2) 0.0321(7) Uani d . 1 . .
C C3 0.3745(9) 0.4065(3) 0.2827(2) 0.0313(7) Uani d . 1 . .
C C4 0.4667(8) 0.5359(3) 0.2763(2) 0.0307(7) Uani d . 1 . .
C C5 0.3757(9) 0.6407(3) 0.3694(2) 0.0332(7) Uani d . 1 . .
C C6 0.6205(9) 0.5770(3) 0.2066(2) 0.0338(7) Uani d . 1 . .
C C7 0.6996(10) 0.7183(4) 0.2171(2) 0.0410(8) Uani d . 1 . .
C C8 0.7155(9) 0.4789(4) 0.1207(2) 0.0383(8) Uani d . 1 . .
C C9 0.4316(9) 0.2742(3) 0.2169(2) 0.0364(8) Uani d . 1 . .
H H1 0.152(10) 0.608(4) 0.482(3) 0.051(11) Uiso d . 1 . .
H H31 1.007(13) -0.096(5) 0.107(4) 0.085(17) Uiso d . 1 . .
H H32 0.994(14) -0.211(6) 0.014(4) 0.102(19) Uiso d . 1 . .
H H41 0.041(12) 1.000(5) 0.644(3) 0.067(16) Uiso d . 1 . .
H H42 -0.034(15) 0.867(6) 0.601(4) 0.11(2) Uiso d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1353 0.1239 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 Na1 O3 1_455 . 99.04(10) ?
O3 Na1 N4 . . 93.04(11) ?
O2 Na2 O4 . . 89.06(9) ?
O4 Na2 O4 1_655 . 95.64(10) ?
H31 O3 H32 . . 114(5) ?
H41 O4 H42 . . 108(5) ?
C5 N1 C2 . . 111.2(3) ?
C5 N1 H1 . . 122(2) ?
C2 N1 H1 . . 126(2) ?
C9 N4 Na1 . . 152.8(3) ?
O1 C2 N1 . . 122.6(3) ?
O1 C2 C3 . . 130.0(3) ?
N1 C2 C3 . . 107.4(3) ?
C4 C3 C9 . . 128.0(3) ?
C4 C3 C2 . . 109.2(3) ?
C9 C3 C2 . . 122.7(3) ?
C6 C4 C3 . . 132.7(3) ?
C6 C4 C5 . . 121.4(3) ?
C3 C4 C5 . . 105.9(3) ?
O2 C5 N1 . . 126.1(3) ?
O2 C5 C4 . . 127.8(3) ?
N1 C5 C4 . . 106.2(3) ?
C4 C6 C8 . . 121.4(3) ?
C4 C6 C7 . . 122.5(3) ?
C8 C6 C7 . . 116.0(3) ?
N3 C7 C6 . . 176.4(4) ?
N2 C8 C6 . . 178.5(4) ?
N4 C9 C3 . . 179.0(4) ?
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
Na1 O3 1_455 2.401(3) y
Na1 O3 . 2.404(3) y
Na1 N4 . 2.491(3) y
Na1 Na1 1_455 3.6549(8) y
Na2 O2 . 2.388(2) y
Na2 O4 1_655 2.421(3) y
Na2 O4 . 2.510(3) y
Na2 Na2 1_655 3.6549(8) ?
O2 C5 . 1.211(4) ?
O1 C2 . 1.231(4) ?
O3 H31 . 0.85(5) ?
O3 H32 . 0.93(6) ?
O4 H41 . 0.76(5) ?
O4 H42 . 0.87(6) ?
N1 C5 . 1.367(4) ?
N1 C2 . 1.391(4) ?
N1 H1 . 0.94(4) ?
N2 C8 . 1.149(4) ?
N3 C7 . 1.147(5) ?
N4 C9 . 1.143(4) ?
C2 C3 . 1.431(4) ?
C3 C4 . 1.387(4) ?
C3 C9 . 1.417(4) ?
C4 C6 . 1.382(4) ?
C4 C5 . 1.514(4) ?
C6 C8 . 1.415(4) ?
C6 C7 . 1.417(5) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H32 N2 2_755 0.93(6) 2.03(6) 2.901(4) 155(5)
O3 H31 N3 1_545 0.85(5) 2.28(5) 2.998(4) 142(4)
O4 H41 N3 2_676 0.76(5) 2.21(5) 2.955(5) 170(5)
O4 H42 O1 2_566 0.87(6) 2.05(6) 2.911(4) 171(5)
N1 H1 O1 2_566 0.94(4) 1.91(4) 2.827(3) 165(3)
