#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/57/2225798.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_2225798
loop_
_publ_author_name
'Li, Jian'
'Xu, Ting'
'Wu, Peng-Bo'
'Lu, Jing'
'Tang, Yao'
_publ_section_title
;
 4-(2-Oxa-6-azaspiro[3.3]hept-6-yl)benzonitrile
;
_journal_coeditor_code           CI5062
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1179
_journal_paper_doi               10.1107/S1600536810012936
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H12 N2 O'
_chemical_formula_moiety         'C12 H12 N2 O'
_chemical_formula_sum            'C12 H12 N2 O'
_chemical_formula_weight         200.24
_chemical_name_systematic
;
4-(2-Oxa-6-azaspiro[3.3]hept-6-yl)benzonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 113.186(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.484(4)
_cell_length_b                   11.033(4)
_cell_length_c                   10.419(4)
_cell_measurement_reflns_used    2956
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.08
_cell_volume                     1002.2(7)
_computing_cell_refinement       'CrystalClear (Rigaku, 2008)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Rigaku AFC10/Saturn 724-Plus'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7662
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.08
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0456P)²+0.36P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                1872
_reflns_number_total             2234
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5062.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2225798
_cod_database_fobs_code          2225798
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.53098(12) 0.21116(9) -0.00129(10) 0.0272(3) Uani d . 1 . .
N N1 0.81838(14) 0.46062(12) 1.07793(13) 0.0275(3) Uani d . 1 . .
N N2 0.58259(13) 0.37004(10) 0.38573(11) 0.0186(3) Uani d . 1 . .
C C1 0.74599(15) 0.47583(12) 0.59326(14) 0.0178(3) Uani d . 1 . .
H H1 0.7933 0.5192 0.5421 0.021 Uiso calc R 1 . .
C C2 0.79050(15) 0.49646(12) 0.73352(14) 0.0186(3) Uani d . 1 . .
H H2 0.8679 0.5547 0.7788 0.022 Uiso calc R 1 . .
C C3 0.72270(15) 0.43219(12) 0.81086(14) 0.0177(3) Uani d . 1 . .
C C4 0.60810(15) 0.34638(12) 0.74350(14) 0.0183(3) Uani d . 1 . .
H H4 0.5624 0.3022 0.7954 0.022 Uiso calc R 1 . .
C C5 0.56183(15) 0.32601(12) 0.60278(14) 0.0178(3) Uani d . 1 . .
H H5 0.4835 0.2683 0.5577 0.021 Uiso calc R 1 . .
C C6 0.62984(14) 0.39026(12) 0.52463(13) 0.0165(3) Uani d . 1 . .
C C7 0.49702(15) 0.26581(12) 0.30534(14) 0.0178(3) Uani d . 1 . .
H H7A 0.3842 0.2751 0.2702 0.021 Uiso calc R 1 . .
H H7B 0.5303 0.1871 0.3534 0.021 Uiso calc R 1 . .
C C8 0.56407(14) 0.29329(12) 0.19522(14) 0.0167(3) Uani d . 1 . .
C C9 0.65782(15) 0.39702(12) 0.28976(13) 0.0177(3) Uani d . 1 . .
H H9A 0.7699 0.3827 0.3302 0.021 Uiso calc R 1 . .
H H9B 0.6331 0.4782 0.2461 0.021 Uiso calc R 1 . .
C C10 0.45979(16) 0.31151(12) 0.04116(14) 0.0204(3) Uani d . 1 . .
H H10A 0.3499 0.2979 0.0208 0.024 Uiso calc R 1 . .
H H10B 0.4749 0.3907 0.0037 0.024 Uiso calc R 1 . .
C C11 0.63751(16) 0.19237(13) 0.14221(14) 0.0226(3) Uani d . 1 . .
H H11A 0.7455 0.2092 0.1575 0.027 Uiso calc R 1 . .
H H11B 0.6281 0.1114 0.1790 0.027 Uiso calc R 1 . .
C C12 0.77569(15) 0.44870(12) 0.95891(15) 0.0202(3) Uani d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O1 C10 . . 90.79(9) ?
C6 N2 C7 . . 128.02(11) ?
C6 N2 C9 . . 130.44(11) ?
C7 N2 C9 . . 94.47(10) ?
C2 C1 C6 . . 120.13(12) ?
C2 C1 H1 . . 119.9 ?
C6 C1 H1 . . 119.9 ?
C1 C2 C3 . . 120.61(12) ?
C1 C2 H2 . . 119.7 ?
C3 C2 H2 . . 119.7 ?
C4 C3 C2 . . 119.53(12) ?
C4 C3 C12 . . 119.89(12) ?
C2 C3 C12 . . 120.49(12) ?
C5 C4 C3 . . 120.22(12) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C4 C5 C6 . . 120.45(12) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
N2 C6 C5 . . 119.95(12) ?
N2 C6 C1 . . 121.00(12) ?
C5 C6 C1 . . 119.05(12) ?
N2 C7 C8 . . 88.47(10) ?
N2 C7 H7A . . 113.9 ?
C8 C7 H7A . . 113.9 ?
N2 C7 H7B . . 113.9 ?
C8 C7 H7B . . 113.9 ?
H7A C7 H7B . . 111.1 ?
C11 C8 C10 . . 85.12(10) ?
C11 C8 C9 . . 122.78(11) ?
C10 C8 C9 . . 122.94(11) ?
C11 C8 C7 . . 120.34(11) ?
C10 C8 C7 . . 121.30(11) ?
C9 C8 C7 . . 88.49(10) ?
N2 C9 C8 . . 88.40(10) ?
N2 C9 H9A . . 113.9 ?
C8 C9 H9A . . 113.9 ?
N2 C9 H9B . . 113.9 ?
C8 C9 H9B . . 113.9 ?
H9A C9 H9B . . 111.1 ?
O1 C10 C8 . . 91.91(10) ?
O1 C10 H10A . . 113.3 ?
C8 C10 H10A . . 113.3 ?
O1 C10 H10B . . 113.3 ?
C8 C10 H10B . . 113.3 ?
H10A C10 H10B . . 110.6 ?
O1 C11 C8 . . 92.11(10) ?
O1 C11 H11A . . 113.3 ?
C8 C11 H11A . . 113.3 ?
O1 C11 H11B . . 113.3 ?
C8 C11 H11B . . 113.3 ?
H11A C11 H11B . . 110.6 ?
N1 C12 C3 . . 179.26(15) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 . 1.4525(17) ?
O1 C10 . 1.4534(17) ?
N1 C12 . 1.1504(18) ?
N2 C6 . 1.3544(17) ?
N2 C7 . 1.4653(17) ?
N2 C9 . 1.4695(17) ?
C1 C2 . 1.3711(19) ?
C1 C6 . 1.4127(18) ?
C1 H1 . 0.95 ?
C2 C3 . 1.4049(19) ?
C2 H2 . 0.95 ?
C3 C4 . 1.4034(19) ?
C3 C12 . 1.4335(19) ?
C4 C5 . 1.3734(19) ?
C4 H4 . 0.95 ?
C5 C6 . 1.4125(19) ?
C5 H5 . 0.95 ?
C7 C8 . 1.5451(18) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C11 . 1.5274(18) ?
C8 C10 . 1.5314(18) ?
C8 C9 . 1.5431(18) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
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
C4 H4 O1 1_556 0.95 2.47 3.371(2) 159
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 C1 C2 C3 . . . . 0.67(19) ?
C1 C2 C3 C4 . . . . -0.17(18) ?
C1 C2 C3 C12 . . . . 176.30(12) ?
C2 C3 C4 C5 . . . . -0.45(19) ?
C12 C3 C4 C5 . . . . -176.95(12) ?
C3 C4 C5 C6 . . . . 0.57(19) ?
C7 N2 C6 C5 . . . . -18.4(2) ?
C9 N2 C6 C5 . . . . -161.23(13) ?
C7 N2 C6 C1 . . . . 162.08(12) ?
C9 N2 C6 C1 . . . . 19.3(2) ?
C4 C5 C6 N2 . . . . -179.56(12) ?
C4 C5 C6 C1 . . . . -0.07(19) ?
C2 C1 C6 N2 . . . . 178.93(12) ?
C2 C1 C6 C5 . . . . -0.55(19) ?
C6 N2 C7 C8 . . . . -155.71(13) ?
C9 N2 C7 C8 . . . . -3.21(10) ?
N2 C7 C8 C11 . . . . 130.78(12) ?
N2 C7 C8 C10 . . . . -125.31(12) ?
N2 C7 C8 C9 . . . . 3.04(9) ?
C6 N2 C9 C8 . . . . 154.66(13) ?
C7 N2 C9 C8 . . . . 3.21(10) ?
C11 C8 C9 N2 . . . . -128.76(12) ?
C10 C8 C9 N2 . . . . 123.99(12) ?
C7 C8 C9 N2 . . . . -3.04(9) ?
C11 O1 C10 C8 . . . . -2.22(10) ?
C11 C8 C10 O1 . . . . 2.12(10) ?
C9 C8 C10 O1 . . . . 128.42(12) ?
C7 C8 C10 O1 . . . . -120.66(12) ?
C10 O1 C11 C8 . . . . 2.22(10) ?
C10 C8 C11 O1 . . . . -2.12(10) ?
C9 C8 C11 O1 . . . . -128.56(12) ?
C7 C8 C11 O1 . . . . 121.54(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744854
