#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/11/2221109.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_2221109
loop_
_publ_author_name
'Safari, Nasser'
'Amani, Vahid'
'Notash, Behrouz'
'Ng, Seik Weng'
_publ_section_title
;
 9-Oxo-4,5-diazafluoren-4-ium
 tetrachloridoaurate(III)--4,5-diazafluoren-9-one (1/1)
;
_journal_coeditor_code           HY2184
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m344
_journal_paper_doi               10.1107/S1600536809006734
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '(C11 H7 N2 O) [Au Cl4], C11 H6 N2 O'
_chemical_formula_moiety         'C11 H7 N2 O +, Au Cl4 -, C11 H6 N2 O'
_chemical_formula_sum            'C22 H13 Au Cl4 N4 O2'
_chemical_formula_weight         704.13
_chemical_name_systematic
;
9-Oxo-4,5-diazafluoren-4-ium tetrachloridoaurate(III)--4,5-diazafluoren-9-one
(1/1)
;
_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                73.2850(10)
_cell_angle_beta                 78.4100(10)
_cell_angle_gamma                88.3750(10)
_cell_formula_units_Z            2
_cell_length_a                   7.10350(10)
_cell_length_b                   12.6513(2)
_cell_length_c                   13.2366(2)
_cell_measurement_reflns_used    7741
_cell_measurement_temperature    118(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.7
_cell_volume                     1115.51(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      118(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9343
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.103
_exptl_absorpt_correction_T_max  0.5369
_exptl_absorpt_correction_T_min  0.3308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    2.096
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         3.051
_refine_diff_density_min         -1.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5044
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0509P)²+0.1124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0666
_reflns_number_gt                4829
_reflns_number_total             5044
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2184.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               2221109
_cod_database_fobs_code          2221109
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
Au Au1 0.298203(14) 0.304054(8) 0.394619(8) 0.01445(6) Uani d . 1 . .
Cl Cl1 0.28189(13) 0.32712(7) 0.56013(7) 0.02448(17) Uani d . 1 . .
Cl Cl2 0.31382(13) 0.49176(6) 0.32181(7) 0.02314(17) Uani d . 1 . .
Cl Cl3 0.31133(12) 0.28082(6) 0.22834(6) 0.01975(16) Uani d . 1 . .
Cl Cl4 0.28622(13) 0.11653(6) 0.46788(7) 0.02373(17) Uani d . 1 . .
O O1 0.1850(4) 0.3950(2) 0.7782(2) 0.0258(5) Uani d . 1 . .
O O2 0.3590(4) 1.22613(19) 0.9995(2) 0.0239(5) Uani d . 1 . .
N N1 0.2353(4) 0.7025(2) 0.9069(2) 0.0163(5) Uani d D 1 . .
H H1 0.247(6) 0.7760(9) 0.885(3) 0.029(11) Uiso d D 1 . .
N N2 0.2032(4) 0.7897(2) 0.6684(2) 0.0187(5) Uani d . 1 . .
N N3 0.3136(4) 0.9265(2) 0.8548(2) 0.0156(5) Uani d . 1 . .
N N4 0.1257(4) 0.8534(2) 1.0949(2) 0.0168(5) Uani d . 1 . .
C C1 0.2546(5) 0.6495(3) 1.0088(3) 0.0186(6) Uani d . 1 . .
H H1A 0.2662 0.6912 1.0567 0.022 Uiso calc R 1 . .
C C2 0.2576(5) 0.5354(3) 1.0441(3) 0.0203(6) Uani d . 1 . .
H H2 0.2704 0.4994 1.1159 0.024 Uiso calc R 1 . .
C C3 0.2420(5) 0.4737(3) 0.9747(3) 0.0205(6) Uani d . 1 . .
H H3 0.2447 0.3954 0.9977 0.025 Uiso calc R 1 . .
C C4 0.2222(4) 0.5296(3) 0.8712(3) 0.0164(6) Uani d . 1 . .
C C5 0.2212(4) 0.6449(2) 0.8388(2) 0.0153(6) Uani d . 1 . .
C C6 0.2012(4) 0.4900(3) 0.7772(3) 0.0181(6) Uani d . 1 . .
C C7 0.1980(5) 0.5922(3) 0.6874(3) 0.0182(6) Uani d . 1 . .
C C8 0.1879(5) 0.6097(3) 0.5801(3) 0.0212(7) Uani d . 1 . .
H H8 0.1825 0.5501 0.5504 0.025 Uiso calc R 1 . .
C C9 0.1863(5) 0.7187(3) 0.5186(3) 0.0212(7) Uani d . 1 . .
H H9 0.1809 0.7349 0.4445 0.025 Uiso calc R 1 . .
C C10 0.1924(5) 0.8047(3) 0.5642(3) 0.0223(7) Uani d . 1 . .
H H10 0.1888 0.8781 0.5195 0.027 Uiso calc R 1 . .
C C11 0.2057(4) 0.6848(3) 0.7249(3) 0.0155(6) Uani d . 1 . .
C C12 0.3999(4) 0.9788(3) 0.7520(3) 0.0181(6) Uani d . 1 . .
H H12 0.4178 0.9380 0.7009 0.022 Uiso calc R 1 . .
C C13 0.4636(4) 1.0882(3) 0.7171(3) 0.0180(6) Uani d . 1 . .
H H13 0.5212 1.1206 0.6436 0.022 Uiso calc R 1 . .
C C14 0.4435(4) 1.1511(2) 0.7894(3) 0.0176(6) Uani d . 1 . .
H H14 0.4858 1.2264 0.7675 0.021 Uiso calc R 1 . .
C C15 0.3585(4) 1.0977(2) 0.8947(3) 0.0154(6) Uani d . 1 . .
C C16 0.2951(4) 0.9874(2) 0.9225(2) 0.0139(6) Uani d . 1 . .
C C17 0.3142(4) 1.1372(2) 0.9930(3) 0.0165(6) Uani d . 1 . .
C C18 0.2124(4) 1.0415(2) 1.0813(3) 0.0162(6) Uani d . 1 . .
C C19 0.1345(4) 1.0290(3) 1.1887(3) 0.0181(6) Uani d . 1 . .
H H19 0.1383 1.0876 1.2200 0.022 Uiso calc R 1 . .
C C20 0.0503(4) 0.9262(3) 1.2485(3) 0.0199(6) Uani d . 1 . .
H H20 -0.0062 0.9133 1.3226 0.024 Uiso calc R 1 . .
C C21 0.0490(4) 0.8422(3) 1.1996(3) 0.0195(6) Uani d . 1 . .
H H21 -0.0094 0.7729 1.2426 0.023 Uiso calc R 1 . .
C C22 0.2039(4) 0.9522(2) 1.0394(2) 0.0143(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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 '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
Cl1 Au1 Cl3 . . 179.43(3) ?
Cl1 Au1 Cl4 . . 90.27(3) ?
Cl3 Au1 Cl4 . . 89.73(3) ?
Cl1 Au1 Cl2 . . 89.47(3) ?
Cl3 Au1 Cl2 . . 90.55(3) ?
Cl4 Au1 Cl2 . . 179.30(3) ?
C5 N1 C1 . . 120.1(3) ?
C5 N1 H1 . . 122(3) ?
C1 N1 H1 . . 118(3) ?
C11 N2 C10 . . 114.0(3) ?
C16 N3 C12 . . 115.2(3) ?
C22 N4 C21 . . 115.0(3) ?
N1 C1 C2 . . 120.9(3) ?
N1 C1 H1A . . 119.6 ?
C2 C1 H1A . . 119.6 ?
C1 C2 C3 . . 120.1(3) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
C4 C3 C2 . . 118.0(3) ?
C4 C3 H3 . . 121.0 ?
C2 C3 H3 . . 121.0 ?
C3 C4 C5 . . 120.0(3) ?
C3 C4 C6 . . 132.0(3) ?
C5 C4 C6 . . 107.9(3) ?
N1 C5 C4 . . 121.0(3) ?
N1 C5 C11 . . 129.2(3) ?
C4 C5 C11 . . 109.8(3) ?
O1 C6 C7 . . 128.9(3) ?
O1 C6 C4 . . 126.0(3) ?
C7 C6 C4 . . 105.1(3) ?
C8 C7 C11 . . 118.2(3) ?
C8 C7 C6 . . 132.5(3) ?
C11 C7 C6 . . 109.4(3) ?
C9 C8 C7 . . 116.6(3) ?
C9 C8 H8 . . 121.7 ?
C7 C8 H8 . . 121.7 ?
C8 C9 C10 . . 120.7(3) ?
C8 C9 H9 . . 119.7 ?
C10 C9 H9 . . 119.7 ?
N2 C10 C9 . . 123.9(3) ?
N2 C10 H10 . . 118.1 ?
C9 C10 H10 . . 118.1 ?
N2 C11 C7 . . 126.7(3) ?
N2 C11 C5 . . 125.6(3) ?
C7 C11 C5 . . 107.7(3) ?
N3 C12 C13 . . 123.8(3) ?
N3 C12 H12 . . 118.1 ?
C13 C12 H12 . . 118.1 ?
C12 C13 C14 . . 120.3(3) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C15 C14 C13 . . 116.1(3) ?
C15 C14 H14 . . 121.9 ?
C13 C14 H14 . . 121.9 ?
C14 C15 C16 . . 119.8(3) ?
C14 C15 C17 . . 131.3(3) ?
C16 C15 C17 . . 108.9(3) ?
N3 C16 C15 . . 124.8(3) ?
N3 C16 C22 . . 126.9(3) ?
C15 C16 C22 . . 108.3(3) ?
O2 C17 C15 . . 126.5(3) ?
O2 C17 C18 . . 128.0(3) ?
C15 C17 C18 . . 105.4(2) ?
C19 C18 C22 . . 119.4(3) ?
C19 C18 C17 . . 132.1(3) ?
C22 C18 C17 . . 108.5(3) ?
C18 C19 C20 . . 116.5(3) ?
C18 C19 H19 . . 121.8 ?
C20 C19 H19 . . 121.8 ?
C19 C20 C21 . . 120.0(3) ?
C19 C20 H20 . . 120.0 ?
C21 C20 H20 . . 120.0 ?
N4 C21 C20 . . 124.0(3) ?
N4 C21 H21 . . 118.0 ?
C20 C21 H21 . . 118.0 ?
N4 C22 C18 . . 125.2(3) ?
N4 C22 C16 . . 126.0(3) ?
C18 C22 C16 . . 108.8(3) ?
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
Au1 Cl1 . 2.2720(8) y
Au1 Cl2 . 2.2882(8) y
Au1 Cl3 . 2.2864(8) y
Au1 Cl4 . 2.2872(8) y
O1 C6 . 1.208(4) ?
O2 C17 . 1.209(4) ?
N1 C5 . 1.331(4) ?
N1 C1 . 1.355(4) ?
N1 H1 . 0.890(10) ?
N2 C11 . 1.325(4) ?
N2 C10 . 1.355(4) ?
N3 C16 . 1.326(4) ?
N3 C12 . 1.354(4) ?
N4 C22 . 1.326(4) ?
N4 C21 . 1.352(4) ?
C1 C2 . 1.384(4) ?
C1 H1A . 0.9500 ?
C2 C3 . 1.387(5) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.383(5) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.397(4) ?
C4 C6 . 1.503(4) ?
C5 C11 . 1.471(4) ?
C6 C7 . 1.486(5) ?
C7 C8 . 1.389(5) ?
C7 C11 . 1.405(4) ?
C8 C9 . 1.386(5) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.393(5) ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C12 C13 . 1.385(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.396(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.381(4) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.400(4) ?
C15 C17 . 1.498(4) ?
C16 C22 . 1.493(4) ?
C17 C18 . 1.500(4) ?
C18 C19 . 1.382(4) ?
C18 C22 . 1.402(4) ?
C19 C20 . 1.392(4) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.396(4) ?
C20 H20 . 0.9500 ?
C21 H21 . 0.9500 ?
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
N1 H1 N3 . 0.890(10) 1.880(10) 2.762(4) 168(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
C5 N1 C1 C2 . . . . -0.8(5) ?
N1 C1 C2 C3 . . . . 0.4(5) ?
C1 C2 C3 C4 . . . . -0.4(5) ?
C2 C3 C4 C5 . . . . 0.9(5) ?
C2 C3 C4 C6 . . . . -179.7(3) ?
C1 N1 C5 C4 . . . . 1.2(5) ?
C1 N1 C5 C11 . . . . -177.8(3) ?
C3 C4 C5 N1 . . . . -1.3(5) ?
C6 C4 C5 N1 . . . . 179.2(3) ?
C3 C4 C5 C11 . . . . 177.9(3) ?
C6 C4 C5 C11 . . . . -1.6(3) ?
C3 C4 C6 O1 . . . . 5.2(6) ?
C5 C4 C6 O1 . . . . -175.3(3) ?
C3 C4 C6 C7 . . . . -176.8(3) ?
C5 C4 C6 C7 . . . . 2.8(3) ?
O1 C6 C7 C8 . . . . -4.5(6) ?
C4 C6 C7 C8 . . . . 177.6(4) ?
O1 C6 C7 C11 . . . . 175.0(3) ?
C4 C6 C7 C11 . . . . -2.9(3) ?
C11 C7 C8 C9 . . . . 0.0(5) ?
C6 C7 C8 C9 . . . . 179.4(3) ?
C7 C8 C9 C10 . . . . -0.7(5) ?
C11 N2 C10 C9 . . . . -0.6(5) ?
C8 C9 C10 N2 . . . . 1.0(5) ?
C10 N2 C11 C7 . . . . -0.2(5) ?
C10 N2 C11 C5 . . . . 178.5(3) ?
C8 C7 C11 N2 . . . . 0.5(5) ?
C6 C7 C11 N2 . . . . -179.1(3) ?
C8 C7 C11 C5 . . . . -178.4(3) ?
C6 C7 C11 C5 . . . . 2.0(4) ?
N1 C5 C11 N2 . . . . 0.0(5) ?
C4 C5 C11 N2 . . . . -179.1(3) ?
N1 C5 C11 C7 . . . . 178.9(3) ?
C4 C5 C11 C7 . . . . -0.2(4) ?
C16 N3 C12 C13 . . . . -0.8(5) ?
N3 C12 C13 C14 . . . . 1.0(5) ?
C12 C13 C14 C15 . . . . 0.1(5) ?
C13 C14 C15 C16 . . . . -1.3(4) ?
C13 C14 C15 C17 . . . . 179.7(3) ?
C12 N3 C16 C15 . . . . -0.5(4) ?
C12 N3 C16 C22 . . . . 179.1(3) ?
C14 C15 C16 N3 . . . . 1.5(5) ?
C17 C15 C16 N3 . . . . -179.3(3) ?
C14 C15 C16 C22 . . . . -178.0(3) ?
C17 C15 C16 C22 . . . . 1.2(3) ?
C14 C15 C17 O2 . . . . -5.5(6) ?
C16 C15 C17 O2 . . . . 175.4(3) ?
C14 C15 C17 C18 . . . . 177.2(3) ?
C16 C15 C17 C18 . . . . -1.9(3) ?
O2 C17 C18 C19 . . . . 3.9(6) ?
C15 C17 C18 C19 . . . . -178.8(3) ?
O2 C17 C18 C22 . . . . -175.3(3) ?
C15 C17 C18 C22 . . . . 2.0(3) ?
C22 C18 C19 C20 . . . . -0.3(4) ?
C17 C18 C19 C20 . . . . -179.5(3) ?
C18 C19 C20 C21 . . . . 0.4(5) ?
C22 N4 C21 C20 . . . . -0.4(5) ?
C19 C20 C21 N4 . . . . -0.1(5) ?
C21 N4 C22 C18 . . . . 0.5(4) ?
C21 N4 C22 C16 . . . . -178.9(3) ?
C19 C18 C22 N4 . . . . -0.1(5) ?
C17 C18 C22 N4 . . . . 179.2(3) ?
C19 C18 C22 C16 . . . . 179.3(3) ?
C17 C18 C22 C16 . . . . -1.3(3) ?
N3 C16 C22 N4 . . . . 0.0(5) ?
C15 C16 C22 N4 . . . . 179.5(3) ?
N3 C16 C22 C18 . . . . -179.5(3) ?
C15 C16 C22 C18 . . . . 0.1(3) ?
