#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/12/2211278.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_2211278
loop_
_publ_author_name
'Deshpande, Megha S.'
'Näther, Christian'
'Bensch, Wolfgang'
'Kumbhar, Avinash S.'
_publ_section_title
;
 Bis(1,10-phenanthroline-5,6-dione) diaminoglyoxime
;
_journal_coeditor_code           BH2052
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5910
_journal_page_last               o5912
_journal_paper_doi               10.1107/S1600536806049397
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '2C12 H6 N2 O2, C2 H6 N4 O2'
_chemical_formula_moiety         '2(C12 H6 N2 O2), (C2 H6 N4 O2)'
_chemical_formula_sum            'C26 H18 N8 O6'
_chemical_formula_weight         538.48
_chemical_name_systematic
;
Bis(1,10-phenanthroline-5,6-dione) diaminoglyoxime
;
_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           SHELXL97
_cell_angle_alpha                78.712(16)
_cell_angle_beta                 81.427(15)
_cell_angle_gamma                68.269(15)
_cell_formula_units_Z            1
_cell_length_a                   7.1513(8)
_cell_length_b                   9.3637(14)
_cell_length_c                   9.6271(12)
_cell_measurement_reflns_used    2741
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3.5
_cell_volume                     585.18(15)
_computing_cell_refinement       'IPDS Program Package'
_computing_data_collection       'IPDS Program Package (Stoe & Cie, 1998)'
_computing_data_reduction        'IPDS Program Package'
_computing_molecular_graphics
;
SHELXTL (Bruker, 1998) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Stoe IPDS-1'
_diffrn_measurement_method       φ
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3472
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             278
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0476
_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)+(0.0876P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1363
_reflns_number_gt                1395
_reflns_number_total             1991
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2052.cif
_cod_data_source_block           I
_cod_original_cell_volume        585.18(13)
_cod_database_code               2211278
_cod_database_fobs_code          2211278
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
O O1 -0.0596(2) 0.39276(18) 0.77530(17) 0.0469(5) Uani d . 1
O O2 0.1168(3) 0.1953(2) 0.58301(16) 0.0538(5) Uani d . 1
N N1 0.2401(3) -0.0160(2) 1.14428(18) 0.0369(5) Uani d . 1
N N2 0.4397(3) -0.2012(2) 0.95105(18) 0.0349(4) Uani d . 1
C C1 0.0466(3) 0.2604(2) 0.8161(2) 0.0330(5) Uani d . 1
C C2 0.0791(3) 0.1982(2) 0.9673(2) 0.0296(5) Uani d . 1
C C3 -0.0183(4) 0.2898(3) 1.0729(3) 0.0414(6) Uani d . 1
H H3 -0.1058 0.3928 1.0491 0.050 Uiso calc R 1
C C4 0.0155(4) 0.2272(3) 1.2118(3) 0.0484(6) Uani d . 1
H H4 -0.0483 0.2866 1.2851 0.058 Uiso calc R 1
C C5 0.1447(4) 0.0757(3) 1.2424(2) 0.0464(6) Uani d . 1
H H5 0.1671 0.0343 1.3381 0.056 Uiso calc R 1
C C6 0.2083(3) 0.0460(2) 1.0079(2) 0.0274(5) Uani d . 1
C C7 0.3172(3) -0.0578(2) 0.9010(2) 0.0277(5) Uani d . 1
C C8 0.5392(4) -0.2962(3) 0.8578(3) 0.0451(6) Uani d . 1
H H8 0.6241 -0.3970 0.8925 0.054 Uiso calc R 1
C C9 0.5255(4) -0.2559(3) 0.7116(3) 0.0464(6) Uani d . 1
H H9 0.6011 -0.3265 0.6492 0.056 Uiso calc R 1
C C10 0.3983(4) -0.1099(3) 0.6613(2) 0.0406(6) Uani d . 1
H H10 0.3832 -0.0794 0.5634 0.049 Uiso calc R 1
C C11 0.2917(3) -0.0071(2) 0.7566(2) 0.0303(5) Uani d . 1
C C12 0.1518(3) 0.1506(2) 0.7064(2) 0.0343(5) Uani d . 1
O O3 0.4122(3) 0.3105(2) 0.75937(17) 0.0543(5) Uani d . 1
H H1O1 0.4965 0.2558 0.8165 0.081 Uiso d R 1
N N3 0.5422(3) 0.3635(2) 0.65360(19) 0.0427(5) Uani d . 1
H H1N3 0.1713 0.4667 0.6103 0.064 Uiso d R 1
H H2N3 0.1855 0.5876 0.4807 0.064 Uiso d R 1
N N4 0.2380(3) 0.5176(2) 0.55172(19) 0.0421(5) Uani d . 1
C C13 0.4401(3) 0.4660(2) 0.5576(2) 0.0315(5) Uani 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C5 N1 C6 . 117.1(2)
C8 N2 C7 . 117.77(18)
O1 C1 C2 . 123.2(2)
O1 C1 C12 . 118.90(19)
C2 C1 C12 . 117.86(17)
C3 C2 C6 . 118.37(19)
C3 C2 C1 . 120.82(19)
C6 C2 C1 . 120.81(18)
C4 C3 C2 . 118.9(2)
C4 C3 H3 . 120.5
C2 C3 H3 . 120.5
C3 C4 C5 . 118.8(2)
C3 C4 H4 . 120.6
C5 C4 H4 . 120.6
N1 C5 C4 . 124.0(2)
N1 C5 H5 . 118.0
C4 C5 H5 . 118.0
N1 C6 C2 . 122.77(19)
N1 C6 C7 . 115.99(17)
C2 C6 C7 . 121.23(17)
N2 C7 C11 . 122.50(18)
N2 C7 C6 . 116.53(17)
C11 C7 C6 . 120.97(17)
N2 C8 C9 . 124.0(2)
N2 C8 H8 . 118.0
C9 C8 H8 . 118.0
C10 C9 C8 . 117.9(2)
C10 C9 H9 . 121.0
C8 C9 H9 . 121.0
C9 C10 C11 . 119.4(2)
C9 C10 H10 . 120.3
C11 C10 H10 . 120.3
C10 C11 C7 . 118.33(19)
C10 C11 C12 . 120.93(18)
C7 C11 C12 . 120.73(18)
O2 C12 C11 . 122.6(2)
O2 C12 C1 . 119.19(18)
C11 C12 C1 . 118.25(17)
N3 O3 H1O1 . 98.7
C13 N3 O3 . 110.48(19)
C13 N4 H1N3 . 117.3
C13 N4 H2N3 . 118.4
H1N3 N4 H2N3 . 123.3
N3 C13 N4 . 126.7(2)
N3 C13 C13 2_666 115.5(2)
N4 C13 C13 2_666 117.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.212(3)
O2 C12 . 1.211(2)
N1 C5 . 1.336(3)
N1 C6 . 1.343(2)
N2 C8 . 1.326(3)
N2 C7 . 1.343(3)
C1 C2 . 1.476(3)
C1 C12 . 1.534(3)
C2 C3 . 1.394(3)
C2 C6 . 1.397(3)
C3 C4 . 1.370(3)
C3 H3 . 0.9400
C4 C5 . 1.379(4)
C4 H4 . 0.9400
C5 H5 . 0.9400
C6 C7 . 1.484(3)
C7 C11 . 1.395(3)
C8 C9 . 1.393(3)
C8 H8 . 0.9400
C9 C10 . 1.372(3)
C9 H9 . 0.9400
C10 C11 . 1.394(3)
C10 H10 . 0.9400
C11 C12 . 1.478(3)
O3 N3 . 1.417(3)
O3 H1O1 . 0.8300
N3 C13 . 1.283(3)
N4 C13 . 1.350(3)
N4 H1N3 . 0.8701
N4 H2N3 . 0.8701
C13 C13 2_666 1.487(4)
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
_geom_hbond_publ_flag
O3 H1O1 N2 2_657 0.83 2.27 2.984(2) 144.1 yes
O3 H1O1 N1 2_657 0.83 2.34 3.043(3) 142.7 yes
N4 H1N3 O1 . 0.87 2.32 3.166(3) 165.7 yes
N4 H2N3 O2 2_566 0.87 2.42 3.149(3) 142.2 yes
