#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/44/4304452.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_4304452
loop_
_publ_author_name
'Joe B. Gilroy'
'Peter O. Otieno'
'Michael J. Ferguson'
'Robert McDonald'
'Robin G. Hicks'
_publ_section_title
;
Synthesis and Characterization of 3-Cyano- and 3-Nitroformazans,
Nitrogen-Rich Analogues of β-Diketimine Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1279
_journal_page_last               1286
_journal_paper_doi               10.1021/ic7019445
_journal_volume                  47
_journal_year                    2008
_chemical_formula_moiety         'C16 H15 N5 O2'
_chemical_formula_sum            'C16 H15 N5 O2'
_chemical_formula_weight         309.33
_chemical_name_systematic
; 
 ? 
;
_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                62.139(9)
_cell_angle_beta                 74.242(8)
_cell_angle_gamma                72.220(9)
_cell_formula_units_Z            2
_cell_length_a                   7.1822(9)
_cell_length_b                   10.8832(14)
_cell_length_c                   11.6087(12)
_cell_measurement_reflns_used    36
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      12.51
_cell_measurement_theta_min      10.19
_cell_volume                     754.90(17)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker P4/RA'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2771
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 297
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_correction_T_min  0.9525
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker SHELXTL'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0644
_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)+(0.0980P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1547
_refine_ls_wR_factor_ref         0.1829
_reflns_number_gt                1734
_reflns_number_total             2571
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic7019445-file003.cif
_cod_data_source_block           vic0609
_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 
;
_cod_original_cell_volume        754.90(16)
_cod_database_code               4304452
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
O1 O 0.1269(3) 0.1273(2) 0.13220(19) 0.0408(6) Uani 1 1 d . . .
O2 O 0.2701(3) 0.2732(2) 0.27401(19) 0.0422(6) Uani 1 1 d . . .
N1 N 0.2569(4) -0.2086(2) 0.4542(2) 0.0331(6) Uani 1 1 d . . .
N2 N 0.2511(4) -0.0946(2) 0.3453(2) 0.0326(6) Uani 1 1 d . . .
H2N H 0.2275 -0.0100 0.3444 0.039 Uiso 1 1 calc R . .
N3 N 0.2383(3) -0.0815(2) 0.5881(2) 0.0326(6) Uani 1 1 d . . .
N4 N 0.2328(3) 0.0390(2) 0.4852(2) 0.0304(6) Uani 1 1 d . . .
N5 N 0.2432(4) -0.4311(3) 0.7760(3) 0.0530(8) Uani 1 1 d . . .
C1 C 0.2437(4) -0.1942(3) 0.5662(3) 0.0324(7) Uani 1 1 d . . .
C2 C 0.2433(5) -0.3263(3) 0.6836(3) 0.0373(8) Uani 1 1 d . . .
C11 C 0.2844(4) -0.1124(3) 0.2278(3) 0.0306(7) Uani 1 1 d . . .
C12 C 0.2212(4) 0.0064(3) 0.1159(3) 0.0314(7) Uani 1 1 d . . .
C13 C 0.2583(4) -0.0056(3) -0.0037(3) 0.0363(8) Uani 1 1 d . . .
H13 H 0.2162 0.0740 -0.0807 0.044 Uiso 1 1 calc R . .
C14 C 0.3564(5) -0.1341(3) -0.0090(3) 0.0386(8) Uani 1 1 d . . .
H14 H 0.3838 -0.1417 -0.0905 0.046 Uiso 1 1 calc R . .
C15 C 0.4151(5) -0.2513(3) 0.1020(3) 0.0395(8) Uani 1 1 d . . .
H15 H 0.4801 -0.3393 0.0970 0.047 Uiso 1 1 calc R . .
C16 C 0.3793(4) -0.2411(3) 0.2209(3) 0.0349(7) Uani 1 1 d . . .
H16 H 0.4198 -0.3219 0.2975 0.042 Uiso 1 1 calc R . .
C17 C 0.0551(5) 0.2495(3) 0.0217(3) 0.0406(8) Uani 1 1 d . . .
H17A H 0.1668 0.2803 -0.0472 0.049 Uiso 1 1 calc R . .
H17B H -0.0175 0.3263 0.0488 0.049 Uiso 1 1 calc R . .
H17C H -0.0335 0.2261 -0.0127 0.049 Uiso 1 1 calc R . .
C21 C 0.2343(4) 0.1576(3) 0.5036(3) 0.0301(7) Uani 1 1 d . . .
C22 C 0.2519(4) 0.2829(3) 0.3898(3) 0.0318(7) Uani 1 1 d . . .
C23 C 0.2499(4) 0.4054(3) 0.3994(3) 0.0358(8) Uani 1 1 d . . .
H23 H 0.2610 0.4908 0.3222 0.043 Uiso 1 1 calc R . .
C24 C 0.2314(5) 0.4023(3) 0.5227(3) 0.0389(8) Uani 1 1 d . . .
H24 H 0.2320 0.4858 0.5296 0.047 Uiso 1 1 calc R . .
C25 C 0.2121(5) 0.2794(4) 0.6354(3) 0.0427(8) Uani 1 1 d . . .
H25 H 0.1967 0.2794 0.7193 0.051 Uiso 1 1 calc R . .
C26 C 0.2148(4) 0.1572(3) 0.6276(3) 0.0379(8) Uani 1 1 d . . .
H26 H 0.2037 0.0724 0.7056 0.046 Uiso 1 1 calc R . .
C27 C 0.2830(5) 0.3990(3) 0.1554(3) 0.0464(9) Uani 1 1 d . . .
H27A H 0.1677 0.4742 0.1601 0.056 Uiso 1 1 calc R . .
H27B H 0.2859 0.3798 0.0804 0.056 Uiso 1 1 calc R . .
H27C H 0.4041 0.4297 0.1441 0.056 Uiso 1 1 calc R . .
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
C12 O1 C17 118.2(2) . . ?
C22 O2 C27 117.4(2) . . ?
N2 N1 C1 117.3(3) . . ?
N1 N2 C11 116.9(2) . . ?
N4 N3 C1 115.5(2) . . ?
N3 N4 C21 117.1(2) . . ?
N3 C1 N1 132.3(3) . . ?
N3 C1 C2 114.3(3) . . ?
N1 C1 C2 113.4(3) . . ?
N5 C2 C1 179.6(3) . . ?
C16 C11 C12 120.4(3) . . ?
C16 C11 N2 122.1(3) . . ?
C12 C11 N2 117.5(3) . . ?
O1 C12 C11 116.4(3) . . ?
O1 C12 C13 124.5(3) . . ?
C11 C12 C13 119.1(3) . . ?
C14 C13 C12 119.5(3) . . ?
C15 C14 C13 121.0(3) . . ?
C14 C15 C16 120.1(3) . . ?
C15 C16 C11 119.8(3) . . ?
C22 C21 C26 119.4(3) . . ?
C22 C21 N4 116.5(3) . . ?
C26 C21 N4 124.1(3) . . ?
O2 C22 C23 124.6(3) . . ?
O2 C22 C21 115.2(3) . . ?
C23 C22 C21 120.2(3) . . ?
C22 C23 C24 119.5(3) . . ?
C25 C24 C23 120.7(3) . . ?
C26 C25 C24 120.6(3) . . ?
C25 C26 C21 119.7(3) . . ?
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
O1 C12 1.358(3) . ?
O1 C17 1.424(3) . ?
O2 C22 1.366(3) . ?
O2 C27 1.423(3) . ?
N1 N2 1.292(3) . ?
N1 C1 1.355(4) . ?
N2 C11 1.413(4) . ?
N3 N4 1.296(3) . ?
N3 C1 1.353(4) . ?
N4 C21 1.406(4) . ?
N5 C2 1.144(4) . ?
C1 C2 1.447(4) . ?
C11 C16 1.387(4) . ?
C11 C12 1.399(4) . ?
C12 C13 1.402(4) . ?
C13 C14 1.383(4) . ?
C14 C15 1.377(4) . ?
C15 C16 1.385(4) . ?
C21 C22 1.397(4) . ?
C21 C26 1.406(4) . ?
C22 C23 1.383(4) . ?
C23 C24 1.387(4) . ?
C24 C25 1.379(4) . ?
C25 C26 1.369(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N N4 0.88 1.95 2.597(3) 128.8 .
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
C1 N1 N2 C11 174.0(2) . . . . ?
C1 N3 N4 C21 -177.8(2) . . . . ?
N4 N3 C1 N1 4.8(5) . . . . ?
N4 N3 C1 C2 -178.1(2) . . . . ?
N2 N1 C1 N3 -5.3(5) . . . . ?
N2 N1 C1 C2 177.6(2) . . . . ?
N3 C1 C2 N5 -164(100) . . . . ?
N1 C1 C2 N5 14(58) . . . . ?
N1 N2 C11 C16 -20.2(4) . . . . ?
N1 N2 C11 C12 161.1(2) . . . . ?
C17 O1 C12 C11 -178.2(3) . . . . ?
C17 O1 C12 C13 1.9(4) . . . . ?
C16 C11 C12 O1 179.0(3) . . . . ?
N2 C11 C12 O1 -2.3(4) . . . . ?
C16 C11 C12 C13 -1.1(4) . . . . ?
N2 C11 C12 C13 177.6(3) . . . . ?
O1 C12 C13 C14 179.8(3) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C13 C14 C15 1.2(5) . . . . ?
C13 C14 C15 C16 -1.2(5) . . . . ?
C14 C15 C16 C11 0.0(5) . . . . ?
C12 C11 C16 C15 1.2(4) . . . . ?
N2 C11 C16 C15 -177.5(3) . . . . ?
N3 N4 C21 C22 172.7(3) . . . . ?
N3 N4 C21 C26 -8.8(4) . . . . ?
C27 O2 C22 C23 -1.6(5) . . . . ?
C27 O2 C22 C21 178.3(3) . . . . ?
C26 C21 C22 O2 -180.0(3) . . . . ?
N4 C21 C22 O2 -1.4(4) . . . . ?
C26 C21 C22 C23 -0.1(4) . . . . ?
N4 C21 C22 C23 178.5(3) . . . . ?
O2 C22 C23 C24 -179.7(3) . . . . ?
C21 C22 C23 C24 0.4(5) . . . . ?
C22 C23 C24 C25 -1.0(5) . . . . ?
C23 C24 C25 C26 1.3(5) . . . . ?
C24 C25 C26 C21 -1.1(5) . . . . ?
C22 C21 C26 C25 0.4(5) . . . . ?
N4 C21 C26 C25 -178.0(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660774
