#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/62/2226216.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_2226216
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Loh, Wan-Sin'
'Maity, Annada C.'
'Goswami, Shyamaprosad'
_publ_section_title
;
 1,10-Phenanthroline--dithiooxamide (2/1)
;
_journal_coeditor_code           LH5039
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1320
_journal_paper_doi               10.1107/S1600536810016405
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H8 N2, 0.5C2 H4 N2 S2'
_chemical_formula_moiety         'C12 H8 N2, 0.5(C2 H4 N2 S2)'
_chemical_formula_sum            'C13 H10 N3 S'
_chemical_formula_weight         240.30
_chemical_name_systematic
;
1,10-Phenanthroline--dithiooxamide (2/1)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 130.145(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5481(3)
_cell_length_b                   10.0544(3)
_cell_length_c                   13.9960(4)
_cell_measurement_reflns_used    5115
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.08
_cell_measurement_theta_min      2.53
_cell_volume                     1134.65(7)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0742
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22512
_diffrn_reflns_theta_full        30.26
_diffrn_reflns_theta_max         30.26
_diffrn_reflns_theta_min         2.53
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_correction_T_min  0.9311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.235
_refine_diff_density_min         -0.404
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         3374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0764P)²+0.8154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1603
_reflns_number_gt                2307
_reflns_number_total             3374
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5039.cif
_cod_data_source_block           I
_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_cell_volume        1134.65(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226216
_cod_database_fobs_code          2226216
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N N1 0.3548(2) 0.2611(2) 0.34019(17) 0.0185(4) Uani d . 1 . .
N N2 0.5551(2) 0.4592(2) 0.36522(18) 0.0217(4) Uani d . 1 . .
N N3 0.8022(2) 0.9404(2) 0.36819(19) 0.0201(4) Uani d . 1 . .
C C1 0.2582(3) 0.1675(2) 0.3304(2) 0.0217(5) Uani d . 1 . .
H H1A 0.1591 0.1482 0.2512 0.026 Uiso calc R 1 . .
C C2 0.2959(3) 0.0962(2) 0.4317(2) 0.0234(5) Uani d . 1 . .
H H2A 0.2241 0.0313 0.4198 0.028 Uiso calc R 1 . .
C C3 0.4421(3) 0.1243(3) 0.5494(2) 0.0247(5) Uani d . 1 . .
H H3A 0.4698 0.0791 0.6186 0.030 Uiso calc R 1 . .
C C4 0.5493(3) 0.2219(2) 0.5643(2) 0.0193(5) Uani d . 1 . .
C C5 0.7051(3) 0.2534(3) 0.6845(2) 0.0240(5) Uani d . 1 . .
H H5A 0.7382 0.2072 0.7549 0.029 Uiso calc R 1 . .
C C6 0.8035(3) 0.3489(3) 0.6961(2) 0.0236(5) Uani d . 1 . .
H H6A 0.9044 0.3670 0.7746 0.028 Uiso calc R 1 . .
C C7 0.7561(3) 0.4235(2) 0.5902(2) 0.0193(5) Uani d . 1 . .
C C8 0.8544(3) 0.5272(3) 0.6009(2) 0.0248(5) Uani d . 1 . .
H H8A 0.9528 0.5508 0.6790 0.030 Uiso calc R 1 . .
C C9 0.8045(3) 0.5928(3) 0.4964(3) 0.0277(6) Uani d . 1 . .
H H9A 0.8688 0.6604 0.5015 0.033 Uiso calc R 1 . .
C C10 0.6528(3) 0.5553(3) 0.3803(2) 0.0267(5) Uani d . 1 . .
H H10A 0.6190 0.6011 0.3095 0.032 Uiso calc R 1 . .
C C11 0.6054(3) 0.3938(2) 0.4689(2) 0.0182(5) Uani d . 1 . .
C C12 0.4998(3) 0.2896(2) 0.4565(2) 0.0170(4) Uani d . 1 . .
C C13 0.9644(3) 0.9392(2) 0.4567(2) 0.0196(5) Uani d . 1 . .
S S1 1.08871(7) 0.81821(6) 0.47638(6) 0.02354(18) Uani d . 1 . .
H H3C 0.752(4) 0.884(3) 0.314(3) 0.030(8) Uiso d . 1 . .
H H3B 0.754(4) 1.004(3) 0.366(3) 0.032(8) 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 0.0033 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'
S S 0.1246 0.1234 '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
C1 N1 C12 . . 117.8(2) ?
C10 N2 C11 . . 117.2(2) ?
C13 N3 H3C . . 123(2) ?
C13 N3 H3B . . 117(2) ?
H3C N3 H3B . . 120(3) ?
N1 C1 C2 . . 124.2(2) ?
N1 C1 H1A . . 117.9 ?
C2 C1 H1A . . 117.9 ?
C3 C2 C1 . . 118.3(2) ?
C3 C2 H2A . . 120.8 ?
C1 C2 H2A . . 120.8 ?
C2 C3 C4 . . 119.6(2) ?
C2 C3 H3A . . 120.2 ?
C4 C3 H3A . . 120.2 ?
C3 C4 C12 . . 118.0(2) ?
C3 C4 C5 . . 122.0(2) ?
C12 C4 C5 . . 120.0(2) ?
C6 C5 C4 . . 120.7(2) ?
C6 C5 H5A . . 119.7 ?
C4 C5 H5A . . 119.7 ?
C5 C6 C7 . . 121.4(2) ?
C5 C6 H6A . . 119.3 ?
C7 C6 H6A . . 119.3 ?
C8 C7 C11 . . 117.5(2) ?
C8 C7 C6 . . 122.4(2) ?
C11 C7 C6 . . 120.1(2) ?
C9 C8 C7 . . 119.7(2) ?
C9 C8 H8A . . 120.1 ?
C7 C8 H8A . . 120.1 ?
C8 C9 C10 . . 118.2(2) ?
C8 C9 H9A . . 120.9 ?
C10 C9 H9A . . 120.9 ?
N2 C10 C9 . . 124.5(2) ?
N2 C10 H10A . . 117.8 ?
C9 C10 H10A . . 117.8 ?
N2 C11 C7 . . 122.9(2) ?
N2 C11 C12 . . 118.79(19) ?
C7 C11 C12 . . 118.3(2) ?
N1 C12 C4 . . 122.1(2) ?
N1 C12 C11 . . 118.4(2) ?
C4 C12 C11 . . 119.46(19) ?
N3 C13 C13 . 3_776 114.4(3) ?
N3 C13 S1 . . 124.50(19) ?
C13 C13 S1 3_776 . 121.1(2) ?
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
N1 C1 . 1.328(3) ?
N1 C12 . 1.364(3) ?
N2 C10 . 1.326(3) ?
N2 C11 . 1.352(3) ?
N3 C13 . 1.315(3) ?
N3 H3C . 0.81(3) ?
N3 H3B . 0.81(3) ?
C1 C2 . 1.398(3) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.377(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.407(3) ?
C3 H3A . 0.9300 ?
C4 C12 . 1.412(3) ?
C4 C5 . 1.438(3) ?
C5 C6 . 1.344(4) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.433(3) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.408(3) ?
C7 C11 . 1.420(3) ?
C8 C9 . 1.364(4) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.411(3) ?
C9 H9A . 0.9300 ?
C10 H10A . 0.9300 ?
C11 C12 . 1.456(3) ?
C13 C13 3_776 1.535(5) ?
C13 S1 . 1.676(2) ?
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
N3 H3C N1 2_655 0.81(3) 2.08(3) 2.876(3) 167(4) yes
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
C12 N1 C1 C2 . . . . -0.2(3) ?
N1 C1 C2 C3 . . . . 0.2(4) ?
C1 C2 C3 C4 . . . . -0.7(4) ?
C2 C3 C4 C12 . . . . 1.3(4) ?
C2 C3 C4 C5 . . . . -178.6(2) ?
C3 C4 C5 C6 . . . . -178.7(2) ?
C12 C4 C5 C6 . . . . 1.4(4) ?
C4 C5 C6 C7 . . . . 0.8(4) ?
C5 C6 C7 C8 . . . . 177.7(2) ?
C5 C6 C7 C11 . . . . -2.4(3) ?
C11 C7 C8 C9 . . . . -1.3(3) ?
C6 C7 C8 C9 . . . . 178.6(2) ?
C7 C8 C9 C10 . . . . 1.2(4) ?
C11 N2 C10 C9 . . . . 0.3(4) ?
C8 C9 C10 N2 . . . . -0.7(4) ?
C10 N2 C11 C7 . . . . -0.4(3) ?
C10 N2 C11 C12 . . . . 178.7(2) ?
C8 C7 C11 N2 . . . . 0.9(3) ?
C6 C7 C11 N2 . . . . -179.0(2) ?
C8 C7 C11 C12 . . . . -178.2(2) ?
C6 C7 C11 C12 . . . . 1.9(3) ?
C1 N1 C12 C4 . . . . 0.8(3) ?
C1 N1 C12 C11 . . . . -178.8(2) ?
C3 C4 C12 N1 . . . . -1.3(3) ?
C5 C4 C12 N1 . . . . 178.6(2) ?
C3 C4 C12 C11 . . . . 178.2(2) ?
C5 C4 C12 C11 . . . . -1.8(3) ?
N2 C11 C12 N1 . . . . 0.7(3) ?
C7 C11 C12 N1 . . . . 179.81(19) ?
N2 C11 C12 C4 . . . . -178.9(2) ?
C7 C11 C12 C4 . . . . 0.2(3) ?
