#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/41/7004183.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_7004183
loop_
_publ_author_name
'Ilkun, Olesya T.'
'Archibald, Stephen J.'
'Barnes, Charles L.'
'Gerasimchuk, Nikolay'
'Biagioni, Richard'
'Silchenko, Svitlana'
'Gerasimchuk, Olga A.'
'Nemykin, Victor N.'
_publ_section_title
;
 Benz(2-heteroaryl)cyanoximes and their Tl(i) complexes: new room
 temperature blue emitters
;
_journal_issue                   42
_journal_name_full               'Dalton Transactions'
_journal_page_first              5715
_journal_page_last               5729
_journal_paper_doi               10.1039/b803846e
_journal_year                    2008
_chemical_formula_moiety         'C10 H8 N4 O, H2 O'
_chemical_formula_sum            'C10 H10 N4 O2'
_chemical_formula_weight         218.22
_chemical_name_common
alpha-oximino(N-methyl-2-benzimidazolyl)-acetonitrile
_chemical_name_systematic
;
alpha-oximino(N-methyl-2-benzimidazolyl)-acetonitrile
;
_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                96.67(2)
_cell_angle_beta                 109.370(18)
_cell_angle_gamma                99.79(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1446(18)
_cell_length_b                   8.587(2)
_cell_length_c                   8.988(2)
_cell_measurement_reflns_used    158
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      65.53
_cell_measurement_theta_min      6.17
_cell_volume                     503.7(2)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP III (Farrugia, 1997)'
_computing_publication_material
'SHELXL97(Sheldrick, 1997) and WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Stoe IPDS-II image plate'
_diffrn_measurement_method
'ω scans, 160 frames at 2° intervals, exposure time 8 minutes'
_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  0.0692
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13006
_diffrn_reflns_theta_full        34.75
_diffrn_reflns_theta_max         34.75
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lathe
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.084(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         4301
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0854P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1687
_reflns_number_gt                2326
_reflns_number_total             4301
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b803846e.txt
_cod_data_source_block           HBIMCO_H2O-final
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7004183
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2744(2) 0.57908(18) 0.52010(17) 0.0225(3) Uani 1 1 d . . .
C2 C 0.3897(2) 0.71748(18) 0.64780(17) 0.0241(3) Uani 1 1 d . . .
C3 C 0.5153(2) 0.68307(18) 0.79882(19) 0.0265(3) Uani 1 1 d . . .
C4 C 0.1606(2) 0.33327(18) 0.39729(17) 0.0236(3) Uani 1 1 d . . .
C5 C 0.0663(2) 0.42802(18) 0.29018(17) 0.0232(3) Uani 1 1 d . . .
C6 C -0.0738(2) 0.3608(2) 0.13654(18) 0.0266(3) Uani 1 1 d . . .
H6 H -0.1366 0.4241 0.0667 0.032 Uiso 1 1 calc R . .
C7 C -0.1146(3) 0.1954(2) 0.09348(19) 0.0299(3) Uani 1 1 d . . .
H7 H -0.2070 0.1464 -0.0083 0.036 Uiso 1 1 calc R . .
C8 C -0.0213(3) 0.09888(19) 0.1984(2) 0.0296(3) Uani 1 1 d . . .
H8 H -0.0527 -0.0120 0.1643 0.036 Uiso 1 1 calc R . .
C9 C 0.1168(2) 0.16552(19) 0.35150(19) 0.0271(3) Uani 1 1 d . . .
H9 H 0.1779 0.1015 0.4212 0.033 Uiso 1 1 calc R . .
C10 C 0.0853(3) 0.72564(19) 0.30663(19) 0.0272(3) Uani 1 1 d . . .
H10A H -0.0110 0.6915 0.1988 0.041 Uiso 1 1 calc R . .
H10B H 0.2043 0.7969 0.3065 0.041 Uiso 1 1 calc R . .
H10C H 0.0252 0.7807 0.3717 0.041 Uiso 1 1 calc R . .
N1 N 0.28965(19) 0.43116(15) 0.54050(15) 0.0240(2) Uani 1 1 d . . .
N2 N 0.1423(2) 0.58535(15) 0.37199(15) 0.0232(2) Uani 1 1 d . . .
N3 N 0.3777(2) 0.86264(16) 0.63125(16) 0.0281(3) Uani 1 1 d . . .
N4 N 0.6109(2) 0.65835(19) 0.91983(17) 0.0337(3) Uani 1 1 d . . .
O1 O 0.49954(19) 0.97053(14) 0.76659(15) 0.0334(3) Uani 1 1 d D . .
O2 O 0.4655(2) 1.26288(16) 0.77472(16) 0.0376(3) Uani 1 1 d D . .
H1 H 0.467(4) 1.074(2) 0.747(3) 0.045 Uiso 1 1 d D . .
H1W H 0.414(4) 1.326(3) 0.702(3) 0.056 Uiso 1 1 d D . .
H2W H 0.437(4) 1.300(3) 0.863(3) 0.056 Uiso 1 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 113.23(13) . . ?
N1 C1 C2 121.25(13) . . ?
N2 C1 C2 125.52(13) . . ?
N3 C2 C3 120.93(14) . . ?
N3 C2 C1 122.55(14) . . ?
C3 C2 C1 116.48(13) . . ?
N4 C3 C2 177.96(17) . . ?
N1 C4 C9 129.91(14) . . ?
N1 C4 C5 109.62(13) . . ?
C9 C4 C5 120.47(14) . . ?
N2 C5 C6 132.21(14) . . ?
N2 C5 C4 105.61(13) . . ?
C6 C5 C4 122.18(14) . . ?
C7 C6 C5 116.50(15) . . ?
C6 C7 C8 122.17(15) . . ?
C9 C8 C7 121.33(15) . . ?
C8 C9 C4 117.35(15) . . ?
C1 N1 C4 105.17(12) . . ?
C1 N2 C5 106.36(12) . . ?
C1 N2 C10 128.94(13) . . ?
C5 N2 C10 124.69(13) . . ?
C2 N3 O1 111.61(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.322(2) . ?
C1 N2 1.366(2) . ?
C1 C2 1.460(2) . ?
C2 N3 1.286(2) . ?
C2 C3 1.453(2) . ?
C3 N4 1.142(2) . ?
C4 N1 1.383(2) . ?
C4 C9 1.402(2) . ?
C4 C5 1.407(2) . ?
C5 N2 1.384(2) . ?
C5 C6 1.394(2) . ?
C6 C7 1.382(2) . ?
C7 C8 1.405(2) . ?
C8 C9 1.385(2) . ?
C10 N2 1.461(2) . ?
N3 O1 1.3629(19) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N3 -179.94(15) . . . . ?
N2 C1 C2 N3 -0.4(2) . . . . ?
N1 C1 C2 C3 -2.1(2) . . . . ?
N2 C1 C2 C3 177.42(14) . . . . ?
N1 C4 C5 N2 0.27(16) . . . . ?
C9 C4 C5 N2 -179.96(13) . . . . ?
N1 C4 C5 C6 -179.30(14) . . . . ?
C9 C4 C5 C6 0.5(2) . . . . ?
N2 C5 C6 C7 179.95(15) . . . . ?
C4 C5 C6 C7 -0.6(2) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C7 C8 C9 C4 -0.4(2) . . . . ?
N1 C4 C9 C8 179.77(14) . . . . ?
C5 C4 C9 C8 0.1(2) . . . . ?
N2 C1 N1 C4 0.22(16) . . . . ?
C2 C1 N1 C4 179.77(13) . . . . ?
C9 C4 N1 C1 179.96(16) . . . . ?
C5 C4 N1 C1 -0.30(16) . . . . ?
N1 C1 N2 C5 -0.05(17) . . . . ?
C2 C1 N2 C5 -179.58(13) . . . . ?
N1 C1 N2 C10 179.51(14) . . . . ?
C2 C1 N2 C10 0.0(2) . . . . ?
C6 C5 N2 C1 179.37(16) . . . . ?
C4 C5 N2 C1 -0.14(15) . . . . ?
C6 C5 N2 C10 -0.2(2) . . . . ?
C4 C5 N2 C10 -179.72(13) . . . . ?
C3 C2 N3 O1 2.3(2) . . . . ?
C1 C2 N3 O1 -179.90(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652670
