#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/44/4304453.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_4304453
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         'C15 H15 N5 O2'
_chemical_formula_sum            'C15 H15 N5 O2'
_chemical_formula_weight         297.32
_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                110.419(2)
_cell_angle_beta                 96.245(2)
_cell_angle_gamma                105.752(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2118(10)
_cell_length_b                   9.8215(14)
_cell_length_c                   11.7772(16)
_cell_measurement_reflns_used    1562
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.89
_cell_measurement_theta_min      2.35
_cell_volume                     733.01(18)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector'
_diffrn_measurement_method       '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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5484
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_correction_T_min  0.9527
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker SHELXTL (Bruker, 1997)'
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0474
_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)+(0.0715P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1370
_reflns_number_gt                1910
_reflns_number_total             2972
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic7019445-file004.cif
_cod_data_source_block           vic0502
_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_database_code               4304453
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 0.5527(2) 0.83659(16) 0.39211(14) 0.0541(4) Uani 1 1 d . . .
O2 O 0.5843(2) 0.85695(16) 0.58224(14) 0.0533(4) Uani 1 1 d . . .
N1 N 0.4022(2) 0.53722(18) 0.31300(15) 0.0361(4) Uani 1 1 d . . .
N2 N 0.3212(2) 0.38812(17) 0.27329(14) 0.0368(4) Uani 1 1 d . . .
H2N H 0.2693 0.3477 0.3233 0.044 Uiso 1 1 calc R . .
N3 N 0.3247(2) 0.58752(17) 0.51958(14) 0.0335(4) Uani 1 1 d . . .
N4 N 0.2316(2) 0.44365(17) 0.48975(14) 0.0340(4) Uani 1 1 d . . .
N5 N 0.5193(2) 0.78300(18) 0.46970(16) 0.0384(4) Uani 1 1 d . . .
C1 C 0.4031(3) 0.6203(2) 0.42868(17) 0.0329(4) Uani 1 1 d . . .
C11 C 0.3157(3) 0.2916(2) 0.15187(17) 0.0352(4) Uani 1 1 d . . .
C12 C 0.2675(4) 0.1362(2) 0.1242(2) 0.0525(6) Uani 1 1 d . . .
H12 H 0.2427 0.0985 0.1871 0.063 Uiso 1 1 calc R . .
C13 C 0.2550(4) 0.0350(2) 0.00564(19) 0.0573(7) Uani 1 1 d . . .
H13 H 0.2227 -0.0717 -0.0118 0.069 Uiso 1 1 calc R . .
C14 C 0.2887(3) 0.0859(2) -0.08876(18) 0.0428(5) Uani 1 1 d . . .
C15 C 0.3392(3) 0.2421(2) -0.05904(19) 0.0450(5) Uani 1 1 d . . .
H15 H 0.3646 0.2798 -0.1219 0.054 Uiso 1 1 calc R . .
C16 C 0.3541(3) 0.3460(2) 0.05996(19) 0.0437(5) Uani 1 1 d . . .
H16 H 0.3901 0.4531 0.0782 0.052 Uiso 1 1 calc R . .
C17 C 0.2684(4) -0.0257(3) -0.2184(2) 0.0612(7) Uani 1 1 d . . .
H17A H 0.1496 -0.1156 -0.2410 0.073 Uiso 1 1 calc R . .
H17B H 0.3850 -0.0588 -0.2224 0.073 Uiso 1 1 calc R . .
H17C H 0.2575 0.0243 -0.2766 0.073 Uiso 1 1 calc R . .
C21 C 0.1427(2) 0.4085(2) 0.58168(17) 0.0323(4) Uani 1 1 d . . .
C22 C 0.0349(3) 0.2542(2) 0.54985(18) 0.0375(5) Uani 1 1 d . . .
H22 H 0.0253 0.1797 0.4701 0.045 Uiso 1 1 calc R . .
C23 C -0.0576(3) 0.2094(2) 0.63323(19) 0.0402(5) Uani 1 1 d . . .
H23 H -0.1312 0.1039 0.6100 0.048 Uiso 1 1 calc R . .
C24 C -0.0454(3) 0.3155(2) 0.75081(19) 0.0393(5) Uani 1 1 d . . .
C25 C 0.0652(3) 0.4692(2) 0.78141(19) 0.0421(5) Uani 1 1 d . . .
H25 H 0.0765 0.5435 0.8617 0.051 Uiso 1 1 calc R . .
C26 C 0.1582(3) 0.5163(2) 0.69936(18) 0.0390(5) Uani 1 1 d . . .
H26 H 0.2325 0.6217 0.7227 0.047 Uiso 1 1 calc R . .
C27 C -0.1498(3) 0.2655(3) 0.8404(2) 0.0542(6) Uani 1 1 d . . .
H27A H -0.2646 0.1726 0.7939 0.065 Uiso 1 1 calc R . .
H27B H -0.1939 0.3479 0.8915 0.065 Uiso 1 1 calc R . .
H27C H -0.0591 0.2433 0.8942 0.065 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
N2 N1 C1 117.19(15) . . ?
N1 N2 C11 120.75(15) . . ?
N4 N3 C1 114.59(15) . . ?
N3 N4 C21 115.24(15) . . ?
O1 N5 O2 123.66(16) . . ?
O1 N5 C1 119.20(16) . . ?
O2 N5 C1 117.08(15) . . ?
N1 C1 N3 134.25(17) . . ?
N1 C1 N5 113.11(16) . . ?
N3 C1 N5 112.61(15) . . ?
C12 C11 C16 119.48(18) . . ?
C12 C11 N2 117.65(17) . . ?
C16 C11 N2 122.86(17) . . ?
C11 C12 C13 120.37(19) . . ?
C12 C13 C14 121.36(19) . . ?
C15 C14 C13 117.51(18) . . ?
C15 C14 C17 121.55(19) . . ?
C13 C14 C17 120.94(19) . . ?
C14 C15 C16 122.00(19) . . ?
C11 C16 C15 119.27(18) . . ?
C26 C21 C22 119.33(17) . . ?
C26 C21 N4 124.36(16) . . ?
C22 C21 N4 116.31(16) . . ?
C23 C22 C21 120.38(18) . . ?
C22 C23 C24 121.18(18) . . ?
C23 C24 C25 117.56(18) . . ?
C23 C24 C27 120.69(19) . . ?
C25 C24 C27 121.75(19) . . ?
C26 C25 C24 122.14(19) . . ?
C25 C26 C21 119.42(17) . . ?
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 N5 1.2185(19) . ?
O2 N5 1.230(2) . ?
N1 N2 1.305(2) . ?
N1 C1 1.320(2) . ?
N2 C11 1.402(2) . ?
N3 N4 1.2877(19) . ?
N3 C1 1.357(2) . ?
N4 C21 1.412(2) . ?
N5 C1 1.462(2) . ?
C11 C12 1.377(3) . ?
C11 C16 1.386(3) . ?
C12 C13 1.378(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.380(3) . ?
C14 C17 1.501(3) . ?
C15 C16 1.388(3) . ?
C21 C26 1.390(2) . ?
C21 C22 1.393(2) . ?
C22 C23 1.374(3) . ?
C23 C24 1.389(3) . ?
C24 C25 1.396(3) . ?
C24 C27 1.501(3) . ?
C25 C26 1.372(3) . ?
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 1.94 2.606(2) 131.1 .
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 -179.45(16) . . . . ?
C1 N3 N4 C21 -177.69(15) . . . . ?
N2 N1 C1 N3 -5.3(3) . . . . ?
N2 N1 C1 N5 172.41(14) . . . . ?
N4 N3 C1 N1 1.9(3) . . . . ?
N4 N3 C1 N5 -175.82(14) . . . . ?
O1 N5 C1 N1 21.4(2) . . . . ?
O2 N5 C1 N1 -155.96(16) . . . . ?
O1 N5 C1 N3 -160.32(16) . . . . ?
O2 N5 C1 N3 22.3(2) . . . . ?
N1 N2 C11 C12 166.44(17) . . . . ?
N1 N2 C11 C16 -14.4(3) . . . . ?
C16 C11 C12 C13 -0.8(3) . . . . ?
N2 C11 C12 C13 178.4(2) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C12 C13 C14 C17 -178.0(2) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C17 C14 C15 C16 178.5(2) . . . . ?
C12 C11 C16 C15 1.3(3) . . . . ?
N2 C11 C16 C15 -177.89(18) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
N3 N4 C21 C26 -2.9(3) . . . . ?
N3 N4 C21 C22 177.69(15) . . . . ?
C26 C21 C22 C23 0.9(3) . . . . ?
N4 C21 C22 C23 -179.65(17) . . . . ?
C21 C22 C23 C24 -0.4(3) . . . . ?
C22 C23 C24 C25 -0.4(3) . . . . ?
C22 C23 C24 C27 179.02(18) . . . . ?
C23 C24 C25 C26 0.6(3) . . . . ?
C27 C24 C25 C26 -178.82(19) . . . . ?
C24 C25 C26 C21 0.0(3) . . . . ?
C22 C21 C26 C25 -0.7(3) . . . . ?
N4 C21 C26 C25 179.89(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28585409
