#------------------------------------------------------------------------------
#$Date: 2016-02-20 17:35:30 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/75/2217520.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_2217520
loop_
_publ_author_name
'Yi Deng'
'Yan-xue Chen'
'Zhi-lei Gao'
'Jin-hui Yang'
'Wei Wang'
_publ_section_title
;
 3,3'-(2-Oxocyclopentane-1,3-diyl)dipropanenitrile
;
_journal_coeditor_code           HB2685
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o391
_journal_page_last               o391
_journal_paper_doi               10.1107/S1600536807068535
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C11 H14 N2 O'
_chemical_formula_moiety         'C11 H14 N2 O'
_chemical_formula_sum            'C11 H14 N2 O'
_chemical_formula_weight         190.24
_chemical_name_systematic
;
3,3'-(2-Oxocyclopentane-1,3-diyl)dipropanenitrile
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 111.510(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.261(3)
_cell_length_b                   7.8182(10)
_cell_length_c                   8.1943(11)
_cell_measurement_reflns_used    798
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.58
_cell_measurement_theta_min      2.87
_cell_volume                     1088.4(3)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART 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  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3003
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.40
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         1114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0588P)²+0.1398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1330
_reflns_number_gt                644
_reflns_number_total             1114
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2685.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2217520
_cod_database_fobs_code          2217520
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
O O1 1.0000 1.0500(2) 0.2500 0.0639(6) Uani d S 1
N N1 0.69534(13) 0.8243(3) -0.3591(3) 0.0968(8) Uani d . 1
C C1 1.0000 0.8948(3) 0.2500 0.0495(7) Uani d S 1
C C2 0.95717(10) 0.7841(2) 0.0927(2) 0.0491(5) Uani d . 1
H H2 0.9889 0.7818 0.0189 0.059 Uiso calc R 1
C C3 0.96129(10) 0.6064(2) 0.1722(2) 0.0555(5) Uani d . 1
H H3A 0.9174 0.5874 0.2097 0.067 Uiso calc R 1
H H3B 0.9609 0.5184 0.0884 0.067 Uiso calc R 1
C C4 0.87656(11) 0.8505(2) -0.0189(2) 0.0579(6) Uani d . 1
H H4A 0.8805 0.9706 -0.0443 0.069 Uiso calc R 1
H H4B 0.8417 0.8409 0.0461 0.069 Uiso calc R 1
C C5 0.84170(11) 0.7522(3) -0.1902(3) 0.0627(6) Uani d . 1
H H5A 0.8720 0.7769 -0.2630 0.075 Uiso calc R 1
H H5B 0.8460 0.6305 -0.1651 0.075 Uiso calc R 1
C C6 0.75994(14) 0.7945(3) -0.2864(3) 0.0672(6) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0821(14) 0.0465(12) 0.0598(12) 0.000 0.0223(10) 0.000
N1 0.0764(15) 0.1164(18) 0.0812(15) 0.0217(12) 0.0096(11) -0.0174(13)
C1 0.0539(15) 0.0485(17) 0.0538(16) 0.000 0.0286(13) 0.000
C2 0.0550(11) 0.0493(11) 0.0462(11) 0.0005(8) 0.0222(9) -0.0018(8)
C3 0.0605(11) 0.0496(11) 0.0569(11) -0.0020(9) 0.0221(9) -0.0027(9)
C4 0.0598(12) 0.0566(12) 0.0554(12) 0.0026(9) 0.0191(10) -0.0027(10)
C5 0.0624(14) 0.0638(12) 0.0570(13) 0.0006(10) 0.0159(11) -0.0072(10)
C6 0.0680(14) 0.0697(15) 0.0570(13) 0.0067(12) 0.0147(11) -0.0095(11)
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_3
_geom_angle
O1 C1 C2 . . 124.94(10)
O1 C1 C2 . 2_755 124.95(10)
C2 C1 C2 . 2_755 110.1(2)
C1 C2 C4 . . 113.82(14)
C1 C2 C3 . . 103.22(15)
C4 C2 C3 . . 117.13(15)
C1 C2 H2 . . 107.4
C4 C2 H2 . . 107.4
C3 C2 H2 . . 107.4
C3 C3 C2 2_755 . 104.12(10)
C3 C3 H3A 2_755 . 110.9
C2 C3 H3A . . 110.9
C3 C3 H3B 2_755 . 110.9
C2 C3 H3B . . 110.9
H3A C3 H3B . . 109.0
C2 C4 C5 . . 111.70(15)
C2 C4 H4A . . 109.3
C5 C4 H4A . . 109.3
C2 C4 H4B . . 109.3
C5 C4 H4B . . 109.3
H4A C4 H4B . . 107.9
C6 C5 C4 . . 112.71(17)
C6 C5 H5A . . 109.1
C4 C5 H5A . . 109.1
C6 C5 H5B . . 109.1
C4 C5 H5B . . 109.1
H5A C5 H5B . . 107.8
N1 C6 C5 . . 178.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.213(3)
N1 C6 . 1.134(3)
C1 C2 . 1.511(2)
C1 C2 2_755 1.511(2)
C2 C4 . 1.512(2)
C2 C3 . 1.525(2)
C2 H2 . 0.9800
C3 C3 2_755 1.518(3)
C3 H3A . 0.9700
C3 H3B . 0.9700
C4 C5 . 1.521(2)
C4 H4A . 0.9700
C4 H4B . 0.9700
C5 C6 . 1.448(3)
C5 H5A . 0.9700
C5 H5B . 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
C5 H5B N1 4_644 0.97 2.54 3.466(3) 160
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_4
_geom_torsion
O1 C1 C2 C4 . . -39.96(17)
C2 C1 C2 C4 2_755 . 140.04(17)
O1 C1 C2 C3 . . -167.96(8)
C2 C1 C2 C3 2_755 . 12.04(8)
C1 C2 C3 C3 . 2_755 -31.6(2)
C4 C2 C3 C3 . 2_755 -157.50(18)
C1 C2 C4 C5 . . 170.57(15)
C3 C2 C4 C5 . . -69.0(2)
C2 C4 C5 C6 . . 170.72(17)
