#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/98/2239851.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2239851
loop_
_publ_author_name
'Harrison, William T. A.'
'Al-Sakka, Ola K.'
'Fleita, Daisy H.'
'Saleh, Amina'
'Salem, Sara'
_publ_section_title
;
 Crystal structure of 2-cyano-N'-(cyclohexylidene)acetohydrazide
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o886
_journal_paper_doi               10.1107/S1600536814009350
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C9 H13 N3 O'
_chemical_formula_moiety         'C9 H13 N3 O'
_chemical_formula_sum            'C9 H13 N3 O'
_chemical_formula_weight         179.22
_chemical_name_systematic
;
2-Cyano-N'-(cyclohexylidene)acetohydrazide
;
_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                73.917(9)
_cell_angle_beta                 82.819(10)
_cell_angle_gamma                75.980(9)
_cell_formula_units_Z            2
_cell_length_a                   4.8420(2)
_cell_length_b                   9.7407(7)
_cell_length_c                   10.7071(8)
_cell_measurement_reflns_used    5790
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     469.87(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 2012)'
_computing_data_collection       'CrystalClear (Rigaku, 2012)'
_computing_data_reduction        'CrystalClear (Rigaku, 2012)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6176
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.58
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut slab'
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0351
_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)+(0.0528P)²+0.0762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                1789
_reflns_number_total             2136
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su0002sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        469.87(5)
_cod_database_code               2239851
_cod_database_fobs_code          2239851
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.5886(2) 0.25153(11) 0.23432(10) 0.0172(2) Uani d . 1 1
C C2 0.7514(2) 0.14590(11) 0.34545(10) 0.0201(2) Uani d . 1 1
H H2A 0.6664 0.1673 0.4289 0.024 Uiso calc R 1 1
H H2B 0.9522 0.1560 0.3350 0.024 Uiso calc R 1 1
C C3 0.7394(2) -0.01067(12) 0.34647(11) 0.0264(3) Uani d . 1 1
H H3A 0.8587 -0.0815 0.4150 0.032 Uiso calc R 1 1
H H3B 0.5406 -0.0233 0.3673 0.032 Uiso calc R 1 1
C C4 0.8456(3) -0.04206(13) 0.21466(12) 0.0290(3) Uani d . 1 1
H H4A 0.8225 -0.1407 0.2159 0.035 Uiso calc R 1 1
H H4B 1.0513 -0.0415 0.1989 0.035 Uiso calc R 1 1
C C5 0.6822(2) 0.07141(13) 0.10418(11) 0.0272(3) Uani d . 1 1
H H5A 0.4801 0.0636 0.1148 0.033 Uiso calc R 1 1
H H5B 0.7631 0.0511 0.0199 0.033 Uiso calc R 1 1
C C6 0.6986(2) 0.22686(12) 0.10284(10) 0.0217(2) Uani d . 1 1
H H6A 0.8983 0.2385 0.0843 0.026 Uiso calc R 1 1
H H6B 0.5815 0.2992 0.0343 0.026 Uiso calc R 1 1
C C7 -0.0539(2) 0.51593(11) 0.19148(10) 0.0173(2) Uani d . 1 1
C C8 -0.1182(2) 0.51675(11) 0.33402(10) 0.0188(2) Uani d . 1 1
H H8A -0.1150 0.4156 0.3873 0.023 Uiso calc R 1 1
H H8B 0.0320 0.5522 0.3629 0.023 Uiso calc R 1 1
C C9 -0.3962(2) 0.61033(11) 0.35514(10) 0.0190(2) Uani d . 1 1
N N1 0.36168(17) 0.33947(9) 0.26408(8) 0.0176(2) Uani d . 1 1
N N2 0.19288(17) 0.42828(9) 0.16325(8) 0.0183(2) Uani d . 1 1
H H1 0.227(3) 0.4221(14) 0.0801(14) 0.022 Uiso d . 1 1
N N3 -0.61224(19) 0.68227(10) 0.37675(9) 0.0251(2) Uani d . 1 1
O O1 -0.21717(15) 0.59183(8) 0.10701(7) 0.0228(2) Uani d . 1 1
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
N1 C1 C2 116.83(9)
N1 C1 C6 128.63(9)
C2 C1 C6 114.13(8)
C1 C2 C3 108.83(9)
C1 C2 H2A 109.9
C3 C2 H2A 109.9
C1 C2 H2B 109.9
C3 C2 H2B 109.9
H2A C2 H2B 108.3
C4 C3 C2 111.01(9)
C4 C3 H3A 109.4
C2 C3 H3A 109.4
C4 C3 H3B 109.4
C2 C3 H3B 109.4
H3A C3 H3B 108.0
C3 C4 C5 111.44(9)
C3 C4 H4A 109.3
C5 C4 H4A 109.3
C3 C4 H4B 109.3
C5 C4 H4B 109.3
H4A C4 H4B 108.0
C4 C5 C6 111.25(9)
C4 C5 H5A 109.4
C6 C5 H5A 109.4
C4 C5 H5B 109.4
C6 C5 H5B 109.4
H5A C5 H5B 108.0
C1 C6 C5 108.10(9)
C1 C6 H6A 110.1
C5 C6 H6A 110.1
C1 C6 H6B 110.1
C5 C6 H6B 110.1
H6A C6 H6B 108.4
O1 C7 N2 122.06(9)
O1 C7 C8 121.97(9)
N2 C7 C8 115.97(9)
C9 C8 C7 111.64(8)
C9 C8 H8A 109.3
C7 C8 H8A 109.3
C9 C8 H8B 109.3
C7 C8 H8B 109.3
H8A C8 H8B 108.0
N3 C9 C8 177.32(11)
C1 N1 N2 117.65(9)
C7 N2 N1 119.30(9)
C7 N2 H1 116.5(8)
N1 N2 H1 123.6(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.2845(13)
C1 C2 1.5032(14)
C1 C6 1.5036(14)
C2 C3 1.5371(15)
C2 H2A 0.99
C2 H2B 0.99
C3 C4 1.5269(16)
C3 H3A 0.99
C3 H3B 0.99
C4 C5 1.5273(17)
C4 H4A 0.99
C4 H4B 0.99
C5 C6 1.5314(16)
C5 H5A 0.99
C5 H5B 0.99
C6 H6A 0.99
C6 H6B 0.99
C7 O1 1.2306(12)
C7 N2 1.3442(13)
C7 C8 1.5209(14)
C8 C9 1.4622(14)
C8 H8A 0.99
C8 H8B 0.99
C9 N3 1.1457(13)
N1 N2 1.3938(12)
N2 H1 0.900(14)
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
N2 H1 O1 2_565 0.900(14) 2.052(15) 2.9399(12) 168.4(11)
C6 H6B O1 2_565 0.99 2.32 3.2736(13) 161
C8 H8B N3 1_655 0.99 2.41 3.3783(14) 165
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
N1 C1 C2 C3 114.56(10)
C6 C1 C2 C3 -58.72(11)
C1 C2 C3 C4 54.68(12)
C2 C3 C4 C5 -54.91(12)
C3 C4 C5 C6 55.98(12)
N1 C1 C6 C5 -113.10(12)
C2 C1 C6 C5 59.23(11)
C4 C5 C6 C1 -56.13(11)
O1 C7 C8 C9 3.02(14)
N2 C7 C8 C9 -177.51(9)
C2 C1 N1 N2 -173.88(8)
C6 C1 N1 N2 -1.72(16)
O1 C7 N2 N1 -176.79(9)
C8 C7 N2 N1 3.75(13)
C1 N1 N2 C7 176.44(9)
