#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/30/7213036.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7213036
loop_
_publ_author_name
'Booth, Brian L.'
'Costa, Flora A. T.'
'Mahmood, Zahid'
'Pritchard, Robin G.'
'Proença, M. Fernanda'
_publ_section_title
;
 Synthesis of (Z )-N-(2-amino-1,2-dicyanovinyl)formamide
 O-alkyloximes and a study of their cyclization in the presence of base
;
_journal_issue                   13
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1853
_journal_paper_doi               10.1039/a901332f
_journal_year                    1999
_chemical_formula_sum            'C12 H11 N5 O'
_chemical_formula_weight         241.26
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 93.35(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3838(10)
_cell_length_b                   6.6380(10)
_cell_length_c                   10.580(2)
_cell_measurement_temperature    293(2)
_cell_volume                     587.79(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2162
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9815
_exptl_absorpt_correction_T_min  0.9679
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         1132
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0343
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1151
_reflns_number_gt                963
_reflns_number_total             1132
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            901332fsup1.cif
_cod_data_source_block           bo97
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_original_sg_symbol_H-M      'P 2(1)'
_cod_database_code               7213036
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
N1 N 1.0957(2) 0.1886(3) 0.72301(18) 0.0395(5) Uani 1 1 d .
C2 C 1.0294(3) 0.3662(4) 0.6845(3) 0.0476(7) Uani 1 1 d .
N3 N 0.8977(3) 0.3789(3) 0.6179(3) 0.0471(6) Uani 1 1 d .
C4 C 0.8218(3) 0.1989(4) 0.5876(2) 0.0384(5) Uani 1 1 d .
C5 C 0.8763(3) 0.0119(4) 0.6260(2) 0.0359(5) Uani 1 1 d .
C6 C 1.0295(3) 0.0009(4) 0.7007(2) 0.0371(5) Uani 1 1 d .
O7 O 1.23544(17) 0.1959(3) 0.80017(13) 0.0426(4) Uani 1 1 d .
C8 C 1.3721(3) 0.2060(6) 0.7221(2) 0.0512(6) Uani 1 1 d .
H8A H 1.3697 0.3304 0.6739 0.061 Uiso 1 1 calc R
H8B H 1.3701 0.0939 0.6632 0.061 Uiso 1 1 calc R
C9 C 1.5192(3) 0.1972(6) 0.8079(2) 0.0495(6) Uani 1 1 d .
C10 C 1.6061(4) 0.3675(7) 0.8366(4) 0.0760(11) Uani 1 1 d .
H10 H 1.5727 0.4917 0.8041 0.091 Uiso 1 1 calc R
C11 C 1.7455(5) 0.3526(11) 0.9153(5) 0.111(2) Uani 1 1 d .
H11 H 1.8037 0.4680 0.9371 0.133 Uiso 1 1 calc R
C12 C 1.7962(5) 0.1716(14) 0.9599(3) 0.117(2) Uani 1 1 d .
H12 H 1.8912 0.1621 1.0094 0.140 Uiso 1 1 calc R
C13 C 1.7083(5) 0.0030(12) 0.9324(4) 0.111(2) Uani 1 1 d .
H13 H 1.7419 -0.1210 0.9650 0.133 Uiso 1 1 calc R
C15 C 0.6761(3) 0.2138(4) 0.5117(2) 0.0443(6) Uani 1 1 d .
C14 C 1.5716(4) 0.0162(8) 0.8574(3) 0.0759(11) Uani 1 1 d .
H14 H 1.5124 -0.0998 0.8391 0.091 Uiso 1 1 calc R
N16 N 0.5594(3) 0.2210(5) 0.4509(2) 0.0621(7) Uani 1 1 d .
N17 N 0.8016(3) -0.1627(4) 0.6019(2) 0.0476(6) Uani 1 1 d .
N18 N 1.0873(3) -0.1672(4) 0.7387(2) 0.0510(6) Uani 1 1 d .
H2 H 1.087(4) 0.481(6) 0.710(3) 0.053(8) Uiso 1 1 d .
H17A H 0.693(4) -0.169(7) 0.577(3) 0.061(8) Uiso 1 1 d .
H17B H 0.853(4) -0.282(6) 0.628(3) 0.055(8) Uiso 1 1 d .
H18 H 1.183(4) -0.150(6) 0.787(3) 0.056(8) Uiso 1 1 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
C2 N1 C6 125.49(18)
C2 N1 O7 117.6(2)
C6 N1 O7 116.7(2)
N3 C2 N1 123.3(2)
C2 N3 C4 116.3(2)
C5 C4 N3 124.77(18)
C5 C4 C15 119.2(3)
N3 C4 C15 116.0(3)
N17 C5 C4 125.6(2)
N17 C5 C6 116.4(2)
C4 C5 C6 117.9(2)
N18 C6 N1 126.6(2)
N18 C6 C5 121.2(2)
N1 C6 C5 112.2(2)
N1 O7 C8 109.50(15)
O7 C8 C9 107.72(17)
C10 C9 C14 119.0(3)
C10 C9 C8 120.9(4)
C14 C9 C8 120.1(3)
C9 C10 C11 119.3(5)
C12 C11 C10 120.4(5)
C11 C12 C13 120.1(3)
C14 C13 C12 120.0(6)
N16 C15 C4 178.4(3)
C13 C14 C9 121.3(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.355(4)
N1 C6 1.379(3)
N1 O7 1.389(2)
C2 N3 1.277(4)
N3 C4 1.383(4)
C4 C5 1.376(4)
C4 C15 1.426(3)
C5 N17 1.335(4)
C5 C6 1.469(3)
C6 N18 1.273(4)
O7 C8 1.453(3)
C8 C9 1.489(3)
C9 C10 1.369(5)
C9 C14 1.373(6)
C10 C11 1.399(6)
C11 C12 1.350(10)
C12 C13 1.362(10)
C13 C14 1.358(6)
C15 N16 1.139(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10490284
