#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/77/2017789.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_2017789
loop_
_publ_author_name
'Altaf, Muhammad'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 Green chemistry synthesis:
 2-amino-3-[(E)-(2-pyridyl)methylideneamino]but-2-enedinitrile
 monohydrate and
 5-cyano-2-(2-pyridyl)-1-(2-pyridylmethyl)-1H-imidazole-4-carboxamide
;
_journal_coeditor_code           BM3095
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o441
_journal_page_last               o445
_journal_paper_doi               10.1107/S0108270110029021
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H12 N6 O'
_chemical_formula_moiety         'C16 H12 N6 O'
_chemical_formula_sum            'C16 H12 N6 O'
_chemical_formula_weight         304.32
_chemical_name_systematic
;
5-cyano-2-(2-pyridyl)-1-(2-pyridylmethyl)-1H-imidazole-4-carboxamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.950(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7315(4)
_cell_length_b                   15.8398(9)
_cell_length_c                   12.0572(8)
_cell_measurement_reflns_used    17872
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.63
_cell_measurement_theta_min      2.12
_cell_volume                     1471.08(15)
_computing_cell_refinement       'X-AREA (Version 1.23; Stoe & Cie, 2009)'
_computing_data_collection       'X-AREA (Version 1.23; Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32 (Version 1.05; Stoe & Cie, 2009)'
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al., 2006)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'two-circle image plate diffractometer'
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       'φ + ω rotation'
_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  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21034
_diffrn_reflns_theta_full        29.22
_diffrn_reflns_theta_max         29.22
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.174
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression 'Fc* = kFc[1+0.001Fc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3974
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0385
_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)+(0.0509P)²+0.2338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                3241
_reflns_number_total             3974
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm3095.cif
_cod_data_source_block           L2-II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017789
_cod_database_fobs_code          2017789
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 1.01156(12) 0.09860(5) 0.09066(6) 0.0318(3) Uani . . 1.000
N N1 0.75225(13) 0.06697(7) 0.61970(8) 0.0326(3) Uani . . 1.000
N N2 0.84501(12) 0.01621(6) 0.33797(7) 0.0249(2) Uani . . 1.000
N N3 0.89248(11) 0.13893(5) 0.42579(7) 0.0217(2) Uani . . 1.000
N N4 0.93337(15) -0.03545(6) 0.13136(8) 0.0344(3) Uani . . 1.000
N N5 1.10636(14) 0.28099(6) 0.26524(8) 0.0331(3) Uani . . 1.000
N N6 0.65570(13) 0.28481(6) 0.41589(8) 0.0308(3) Uani . . 1.000
C C2 0.75565(13) 0.02001(7) 0.52803(9) 0.0258(3) Uani . . 1.000
C C3 0.69047(15) -0.06181(8) 0.51919(10) 0.0318(3) Uani . . 1.000
C C4 0.61387(16) -0.09495(9) 0.60960(12) 0.0397(4) Uani . . 1.000
C C5 0.60638(17) -0.04636(9) 0.70374(11) 0.0425(4) Uani . . 1.000
C C6 0.67853(18) 0.03328(9) 0.70580(11) 0.0395(4) Uani . . 1.000
C C7 0.83060(13) 0.05831(7) 0.43182(8) 0.0230(3) Uani . . 1.000
C C8 0.91836(13) 0.07055(7) 0.26873(8) 0.0230(3) Uani . . 1.000
C C9 0.94908(12) 0.14691(6) 0.32093(8) 0.0220(3) Uani . . 1.000
C C10 0.95879(14) 0.04588(7) 0.15496(8) 0.0252(3) Uani . . 1.000
C C11 1.03424(14) 0.22090(7) 0.28779(8) 0.0245(3) Uani . . 1.000
C C12 0.89753(14) 0.20790(7) 0.50805(8) 0.0256(3) Uani . . 1.000
C C13 0.72230(14) 0.24958(7) 0.51130(9) 0.0257(3) Uani . . 1.000
C C14 0.63775(16) 0.25007(7) 0.60845(10) 0.0316(3) Uani . . 1.000
C C15 0.47485(17) 0.28696(8) 0.60593(11) 0.0393(4) Uani . . 1.000
C C16 0.40436(17) 0.32329(9) 0.50861(13) 0.0424(4) Uani . . 1.000
C C17 0.49924(16) 0.32127(8) 0.41640(11) 0.0385(4) Uani . . 1.000
H H3 0.69820 -0.09400 0.45330 0.0380 Uiso calc R 1.000
H H4 0.56720 -0.15050 0.60660 0.0480 Uiso calc R 1.000
H H4A 0.957(2) -0.0554(10) 0.0645(12) 0.045(4) Uiso . . 1.000
H H4B 0.906(2) -0.0706(9) 0.1830(12) 0.042(4) Uiso . . 1.000
H H5 0.55250 -0.06730 0.76610 0.0510 Uiso calc R 1.000
H H6 0.67580 0.06590 0.77170 0.0470 Uiso calc R 1.000
H H12A 0.98370 0.25060 0.48910 0.0310 Uiso calc R 1.000
H H12B 0.93520 0.18510 0.58270 0.0310 Uiso calc R 1.000
H H14 0.69030 0.22570 0.67500 0.0380 Uiso calc R 1.000
H H15 0.41270 0.28720 0.67050 0.0470 Uiso calc R 1.000
H H16 0.29320 0.34920 0.50480 0.0510 Uiso calc R 1.000
H H17 0.45080 0.34720 0.34970 0.0460 Uiso calc R 1.000
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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C6 . . . 117.43(11) no
C7 N2 C8 . . . 106.04(9) no
C7 N3 C9 . . . 105.93(8) no
C7 N3 C12 . . . 130.19(8) no
C9 N3 C12 . . . 123.85(8) no
C13 N6 C17 . . . 117.07(10) no
H4A N4 H4B . . . 119.7(14) no
C10 N4 H4B . . . 120.3(9) no
C10 N4 H4A . . . 119.6(10) no
C3 C2 C7 . . . 119.23(10) no
N1 C2 C7 . . . 117.41(10) no
N1 C2 C3 . . . 123.35(10) no
C2 C3 C4 . . . 117.94(11) no
C3 C4 C5 . . . 119.16(13) no
C4 C5 C6 . . . 118.73(12) no
N1 C6 C5 . . . 123.36(12) no
N3 C7 C2 . . . 126.17(9) no
N2 C7 N3 . . . 111.62(9) no
N2 C7 C2 . . . 122.21(10) no
N2 C8 C9 . . . 109.96(9) no
N2 C8 C10 . . . 122.26(10) no
C9 C8 C10 . . . 127.77(10) no
C8 C9 C11 . . . 131.61(9) no
N3 C9 C8 . . . 106.45(8) no
N3 C9 C11 . . . 121.72(9) no
O1 C10 C8 . . . 120.67(10) no
O1 C10 N4 . . . 124.91(10) no
N4 C10 C8 . . . 114.42(9) no
N5 C11 C9 . . . 177.24(11) no
N3 C12 C13 . . . 111.70(9) no
C12 C13 C14 . . . 120.82(10) no
N6 C13 C12 . . . 116.01(9) no
N6 C13 C14 . . . 123.17(10) no
C13 C14 C15 . . . 118.45(11) no
C14 C15 C16 . . . 119.14(12) no
C15 C16 C17 . . . 118.47(12) no
N6 C17 C16 . . . 123.67(12) no
C2 C3 H3 . . . 121.00 no
C4 C3 H3 . . . 121.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 121.00 no
C6 C5 H5 . . . 121.00 no
N1 C6 H6 . . . 118.00 no
C5 C6 H6 . . . 118.00 no
N3 C12 H12A . . . 109.00 no
N3 C12 H12B . . . 109.00 no
C13 C12 H12A . . . 109.00 no
C13 C12 H12B . . . 109.00 no
H12A C12 H12B . . . 108.00 no
C13 C14 H14 . . . 121.00 no
C15 C14 H14 . . . 121.00 no
C14 C15 H15 . . . 120.00 no
C16 C15 H15 . . . 120.00 no
C15 C16 H16 . . . 121.00 no
C17 C16 H16 . . . 121.00 no
N6 C17 H17 . . . 118.00 no
C16 C17 H17 . . . 118.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 . . 1.2327(13) no
N1 C2 . . 1.3344(15) no
N1 C6 . . 1.3377(17) no
N2 C7 . . 1.3264(13) no
N2 C8 . . 1.3569(14) no
N3 C7 . . 1.3678(14) no
N3 C9 . . 1.3789(13) no
N3 C12 . . 1.4738(13) no
N4 C10 . . 1.3302(15) no
N5 C11 . . 1.1476(15) no
N6 C13 . . 1.3408(15) no
N6 C17 . . 1.3410(16) no
N4 H4B . . 0.875(14) no
N4 H4A . . 0.899(15) no
C2 C7 . . 1.4716(15) no
C2 C3 . . 1.3913(17) no
C3 C4 . . 1.3878(18) no
C4 C5 . . 1.377(2) no
C5 C6 . . 1.379(2) no
C8 C9 . . 1.3747(14) no
C8 C10 . . 1.4853(14) no
C9 C11 . . 1.4185(14) no
C12 C13 . . 1.5106(15) no
C13 C14 . . 1.3898(16) no
C14 C15 . . 1.3864(18) no
C15 C16 . . 1.377(2) no
C16 C17 . . 1.384(2) no
C3 H3 . . 0.9500 no
C4 H4 . . 0.9500 no
C5 H5 . . 0.9500 no
C6 H6 . . 0.9500 no
C12 H12A . . 0.9900 no
C12 H12B . . 0.9900 no
C14 H14 . . 0.9500 no
C15 H15 . . 0.9500 no
C16 H16 . . 0.9500 no
C17 H17 . . 0.9500 no
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
N4 H4A O1 3_755 0.899(15) 2.026(15) 2.9231(12) 175.1(14) yes
N4 H4B N2 . 0.875(14) 2.399(14) 2.7633(13) 105.4(11) yes
N4 H4B N5 2_745 0.875(14) 2.436(14) 3.1888(14) 144.5(12) yes
C12 H12B N5 4_555 0.99 2.53 3.3749(14) 144 yes
C3 H3 CgB^i^ . 0.95 2.72 3.5854(15) 151 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
C6 N1 C2 C3 . . . . -1.49(17) no
C6 N1 C2 C7 . . . . 177.67(10) no
C2 N1 C6 C5 . . . . -0.32(19) no
C8 N2 C7 N3 . . . . 0.07(12) no
C8 N2 C7 C2 . . . . 179.89(9) no
C7 N2 C8 C9 . . . . -0.04(10) no
C7 N2 C8 C10 . . . . 178.88(9) no
C9 N3 C7 N2 . . . . -0.08(11) no
C9 N3 C7 C2 . . . . -179.88(9) no
C12 N3 C7 N2 . . . . 177.99(10) no
C12 N3 C7 C2 . . . . -1.81(17) no
C7 N3 C9 C8 . . . . 0.04(12) no
C7 N3 C9 C11 . . . . -175.14(9) no
C12 N3 C9 C8 . . . . -178.18(9) no
C12 N3 C9 C11 . . . . 6.64(15) no
C7 N3 C12 C13 . . . . -77.76(13) no
C9 N3 C12 C13 . . . . 100.01(11) no
C17 N6 C13 C12 . . . . 179.19(10) no
C17 N6 C13 C14 . . . . -0.51(17) no
C13 N6 C17 C16 . . . . -0.79(18) no
N1 C2 C3 C4 . . . . 1.86(17) no
C7 C2 C3 C4 . . . . -177.29(10) no
N1 C2 C7 N2 . . . . 177.90(10) no
N1 C2 C7 N3 . . . . -2.31(16) no
C3 C2 C7 N2 . . . . -2.90(16) no
C3 C2 C7 N3 . . . . 176.89(10) no
C2 C3 C4 C5 . . . . -0.40(18) no
C3 C4 C5 C6 . . . . -1.25(19) no
C4 C5 C6 N1 . . . . 1.7(2) no
N2 C8 C9 N3 . . . . 0.00(11) no
N2 C8 C9 C11 . . . . 174.51(10) no
C10 C8 C9 N3 . . . . -178.85(10) no
C10 C8 C9 C11 . . . . -4.34(18) no
N2 C8 C10 O1 . . . . 173.76(10) no
N2 C8 C10 N4 . . . . -6.38(15) no
C9 C8 C10 O1 . . . . -7.52(17) no
C9 C8 C10 N4 . . . . 172.34(11) no
N3 C12 C13 N6 . . . . -60.05(12) no
N3 C12 C13 C14 . . . . 119.66(11) no
N6 C13 C14 C15 . . . . 1.61(17) no
C12 C13 C14 C15 . . . . -178.08(11) no
C13 C14 C15 C16 . . . . -1.42(18) no
C14 C15 C16 C17 . . . . 0.24(19) no
C15 C16 C17 N6 . . . . 0.9(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654256
