#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/62/2236250.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_2236250
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Quah, Ching Kheng'
'Abdel-Aziz, Hatem A.'
'Ghabbour, Hazem A.'
_publ_section_title
;
 3-Oxo-3-(piperidin-1-yl)propanenitrile
;
_journal_coeditor_code           HB6912
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2726
_journal_paper_doi               10.1107/S1600536812035015
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H12 N2 O'
_chemical_formula_moiety         'C8 H12 N2 O'
_chemical_formula_sum            'C8 H12 N2 O'
_chemical_formula_weight         152.20
_chemical_name_systematic
;
3-Oxo-3-(piperidin-1-yl)propanenitrile
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.4250(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7106(2)
_cell_length_b                   8.9468(2)
_cell_length_c                   9.8487(2)
_cell_measurement_reflns_used    2826
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      70.86
_cell_measurement_theta_min      4.58
_cell_volume                     838.69(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5110
_diffrn_reflns_theta_full        63.00
_diffrn_reflns_theta_max         63.00
_diffrn_reflns_theta_min         4.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  0.7828
_exptl_absorpt_correction_T_min  0.6560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.62
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.299
_refine_ls_extinction_coef       0.82(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0759P)²+0.0948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                1222
_reflns_number_total             1300
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6912.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236250
_cod_database_fobs_code          2236250
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N N1 0.24331(12) 0.06319(12) 0.22467(11) 0.0473(4) Uani d . 1 1
N N2 0.08305(19) 0.56540(17) 0.19855(19) 0.0850(6) Uani d . 1 1
O O1 0.24717(12) 0.26280(12) 0.36568(9) 0.0599(5) Uani d . 1 1
C C1 0.19317(15) -0.01701(16) 0.09524(15) 0.0514(5) Uani d . 1 1
H H1A 0.1452 0.0519 0.0257 0.062 Uiso calc R 1 1
H H1B 0.1266 -0.0934 0.1097 0.062 Uiso calc R 1 1
C C2 0.31440(19) -0.08861(19) 0.04488(17) 0.0637(5) Uani d . 1 1
H H2A 0.3752 -0.0113 0.0205 0.076 Uiso calc R 1 1
H H2B 0.2787 -0.1468 -0.0377 0.076 Uiso calc R 1 1
C C3 0.39850(19) -0.1892(2) 0.15449(19) 0.0683(6) Uani d . 1 1
H H3A 0.3414 -0.2738 0.1705 0.082 Uiso calc R 1 1
H H3B 0.4801 -0.2269 0.1224 0.082 Uiso calc R 1 1
C C4 0.44535(18) -0.10440(19) 0.28805(19) 0.0673(6) Uani d . 1 1
H H4A 0.4908 -0.1729 0.3594 0.081 Uiso calc R 1 1
H H4B 0.5136 -0.0293 0.2751 0.081 Uiso calc R 1 1
C C5 0.32379(19) -0.0296(2) 0.33513(16) 0.0635(5) Uani d . 1 1
H H5A 0.2627 -0.1051 0.3621 0.076 Uiso calc R 1 1
H H5B 0.3590 0.0322 0.4155 0.076 Uiso calc R 1 1
C C6 0.20841(13) 0.20271(15) 0.25256(12) 0.0425(5) Uani d . 1 1
C C7 0.11643(16) 0.28844(15) 0.13497(14) 0.0491(5) Uani d . 1 1
H H7A 0.1588 0.2852 0.0537 0.059 Uiso calc R 1 1
H H7B 0.0250 0.2410 0.1116 0.059 Uiso calc R 1 1
C C8 0.09924(16) 0.44374(17) 0.17336(16) 0.0558(5) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C6 N1 C1 125.76(11)
C6 N1 C5 119.75(11)
C1 N1 C5 113.99(12)
N1 C1 C2 110.43(11)
N1 C1 H1A 109.6
C2 C1 H1A 109.6
N1 C1 H1B 109.6
C2 C1 H1B 109.6
H1A C1 H1B 108.1
C1 C2 C3 111.34(14)
C1 C2 H2A 109.4
C3 C2 H2A 109.4
C1 C2 H2B 109.4
C3 C2 H2B 109.4
H2A C2 H2B 108.0
C4 C3 C2 110.49(13)
C4 C3 H3A 109.6
C2 C3 H3A 109.6
C4 C3 H3B 109.6
C2 C3 H3B 109.6
H3A C3 H3B 108.1
C5 C4 C3 111.85(14)
C5 C4 H4A 109.2
C3 C4 H4A 109.2
C5 C4 H4B 109.2
C3 C4 H4B 109.2
H4A C4 H4B 107.9
N1 C5 C4 110.98(13)
N1 C5 H5A 109.4
C4 C5 H5A 109.4
N1 C5 H5B 109.4
C4 C5 H5B 109.4
H5A C5 H5B 108.0
O1 C6 N1 123.45(12)
O1 C6 C7 119.88(12)
N1 C6 C7 116.67(11)
C8 C7 C6 111.28(11)
C8 C7 H7A 109.4
C6 C7 H7A 109.4
C8 C7 H7B 109.4
C6 C7 H7B 109.4
H7A C7 H7B 108.0
N2 C8 C7 177.51(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.3361(18)
N1 C1 1.4597(16)
N1 C5 1.4650(17)
N2 C8 1.134(2)
O1 C6 1.2271(16)
C1 C2 1.508(2)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C3 1.514(2)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.508(2)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.508(3)
C4 H4A 0.9700
C4 H4B 0.9700
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.5224(18)
C7 C8 1.458(2)
C7 H7A 0.9700
C7 H7B 0.9700
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
C7 H7A O1 4_565 0.97 2.23 3.1922(17) 170 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
C6 N1 C1 C2 131.80(14)
C5 N1 C1 C2 -56.33(17)
N1 C1 C2 C3 55.29(18)
C1 C2 C3 C4 -54.4(2)
C2 C3 C4 C5 53.3(2)
C6 N1 C5 C4 -132.36(14)
C1 N1 C5 C4 55.23(18)
C3 C4 C5 N1 -53.1(2)
C1 N1 C6 O1 175.87(13)
C5 N1 C6 O1 4.4(2)
C1 N1 C6 C7 -4.54(19)
C5 N1 C6 C7 -175.99(12)
O1 C6 C7 C8 6.13(18)
N1 C6 C7 C8 -173.48(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 76469
