#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/91/2229122.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_2229122
loop_
_publ_author_name
'Betz, Richard'
'Gerber, Thomas'
'Schalekamp, Henk'
_publ_section_title
;
 Bis(piperidin-1-yl)methanone
;
_journal_coeditor_code           JH2250
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o397
_journal_paper_doi               10.1107/S1600536811001334
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H20 N2 O'
_chemical_formula_moiety         'C11 H20 N2 O'
_chemical_formula_sum            'C11 H20 N2 O'
_chemical_formula_weight         196.29
_chemical_name_systematic
;
Bis(piperidin-1-yl)methanone
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 90.7910(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.2193(2)
_cell_length_b                   8.8411(4)
_cell_length_c                   9.9699(4)
_cell_measurement_reflns_used    8651
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      3.08
_cell_volume                     548.15(4)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics
'ORTEPIII (Farrugia, 1997) 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      200(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0762
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9446
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.561
_exptl_crystal_size_mid          0.478
_exptl_crystal_size_min          0.346
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1440
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0297
_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)+(0.0480P)²+0.0376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                1415
_reflns_number_total             1440
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2250.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2229122
_cod_database_fobs_code          2229122
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.75245(16) 0.25290(12) 0.64263(10) 0.0360(2) Uani d . 1 . .
N N11 0.67033(16) 0.00453(12) 0.67895(11) 0.0253(2) Uani d . 1 . .
N N21 0.46865(18) 0.19864(11) 0.77644(10) 0.0267(2) Uani d . 1 . .
C C1 0.63894(19) 0.15808(14) 0.69610(11) 0.0233(2) Uani d . 1 . .
C C11 0.48491(19) -0.09425(14) 0.64910(13) 0.0262(2) Uani d . 1 . .
H H11A 0.4449 -0.0855 0.5530 0.031 Uiso calc R 1 . .
H H11B 0.3603 -0.0616 0.7026 0.031 Uiso calc R 1 . .
C C12 0.5389(2) -0.25768(15) 0.68181(14) 0.0304(3) Uani d . 1 . .
H H12A 0.4159 -0.3231 0.6561 0.036 Uiso calc R 1 . .
H H12B 0.5638 -0.2683 0.7796 0.036 Uiso calc R 1 . .
C C13 0.7384(2) -0.30892(16) 0.60767(15) 0.0320(3) Uani d . 1 . .
H H13A 0.7067 -0.3131 0.5102 0.038 Uiso calc R 1 . .
H H13B 0.7795 -0.4118 0.6378 0.038 Uiso calc R 1 . .
C C14 0.9247(2) -0.19995(16) 0.63433(14) 0.0308(3) Uani d . 1 . .
H H14A 0.9702 -0.2073 0.7297 0.037 Uiso calc R 1 . .
H H14B 1.0484 -0.2291 0.5785 0.037 Uiso calc R 1 . .
C C15 0.8609(2) -0.03795(15) 0.60269(13) 0.0283(3) Uani d . 1 . .
H H15A 0.9814 0.0308 0.6260 0.034 Uiso calc R 1 . .
H H15B 0.8298 -0.0278 0.5055 0.034 Uiso calc R 1 . .
C C21 0.4223(2) 0.36023(14) 0.78549(13) 0.0290(3) Uani d . 1 . .
H H21A 0.4544 0.4098 0.6990 0.035 Uiso calc R 1 . .
H H21B 0.5147 0.4067 0.8559 0.035 Uiso calc R 1 . .
C C22 0.1876(2) 0.38427(17) 0.81904(15) 0.0356(3) Uani d . 1 . .
H H22A 0.0962 0.3474 0.7438 0.043 Uiso calc R 1 . .
H H22B 0.1600 0.4938 0.8303 0.043 Uiso calc R 1 . .
C C23 0.1276(2) 0.30111(18) 0.94720(16) 0.0373(3) Uani d . 1 . .
H H23A -0.0295 0.3086 0.9605 0.045 Uiso calc R 1 . .
H H23B 0.2007 0.3493 1.0250 0.045 Uiso calc R 1 . .
C C24 0.1927(2) 0.13496(17) 0.93964(14) 0.0353(3) Uani d . 1 . .
H H24A 0.1689 0.0862 1.0276 0.042 Uiso calc R 1 . .
H H24B 0.1015 0.0827 0.8719 0.042 Uiso calc R 1 . .
C C25 0.4276(2) 0.11891(16) 0.90219(12) 0.0307(3) Uani d . 1 . .
H H25A 0.5200 0.1613 0.9746 0.037 Uiso calc R 1 . .
H H25B 0.4637 0.0105 0.8920 0.037 Uiso calc R 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
C1 N11 C15 . . 115.61(10) ?
C1 N11 C11 . . 119.70(10) ?
C15 N11 C11 . . 112.30(10) ?
C1 N21 C21 . . 116.26(10) ?
C1 N21 C25 . . 121.00(10) ?
C21 N21 C25 . . 112.41(10) ?
O1 C1 N11 . . 122.40(12) ?
O1 C1 N21 . . 121.71(12) ?
N11 C1 N21 . . 115.88(10) ?
N11 C11 C12 . . 110.53(10) ?
N11 C11 H11A . . 109.5 ?
C12 C11 H11A . . 109.5 ?
N11 C11 H11B . . 109.5 ?
C12 C11 H11B . . 109.5 ?
H11A C11 H11B . . 108.1 ?
C11 C12 C13 . . 111.00(11) ?
C11 C12 H12A . . 109.4 ?
C13 C12 H12A . . 109.4 ?
C11 C12 H12B . . 109.4 ?
C13 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
C12 C13 C14 . . 110.45(10) ?
C12 C13 H13A . . 109.6 ?
C14 C13 H13A . . 109.6 ?
C12 C13 H13B . . 109.6 ?
C14 C13 H13B . . 109.6 ?
H13A C13 H13B . . 108.1 ?
C15 C14 C13 . . 111.32(10) ?
C15 C14 H14A . . 109.4 ?
C13 C14 H14A . . 109.4 ?
C15 C14 H14B . . 109.4 ?
C13 C14 H14B . . 109.4 ?
H14A C14 H14B . . 108.0 ?
N11 C15 C14 . . 110.17(10) ?
N11 C15 H15A . . 109.6 ?
C14 C15 H15A . . 109.6 ?
N11 C15 H15B . . 109.6 ?
C14 C15 H15B . . 109.6 ?
H15A C15 H15B . . 108.1 ?
N21 C21 C22 . . 110.00(11) ?
N21 C21 H21A . . 109.7 ?
C22 C21 H21A . . 109.7 ?
N21 C21 H21B . . 109.7 ?
C22 C21 H21B . . 109.7 ?
H21A C21 H21B . . 108.2 ?
C21 C22 C23 . . 111.39(12) ?
C21 C22 H22A . . 109.3 ?
C23 C22 H22A . . 109.3 ?
C21 C22 H22B . . 109.3 ?
C23 C22 H22B . . 109.3 ?
H22A C22 H22B . . 108.0 ?
C22 C23 C24 . . 110.76(12) ?
C22 C23 H23A . . 109.5 ?
C24 C23 H23A . . 109.5 ?
C22 C23 H23B . . 109.5 ?
C24 C23 H23B . . 109.5 ?
H23A C23 H23B . . 108.1 ?
C25 C24 C23 . . 111.02(11) ?
C25 C24 H24A . . 109.4 ?
C23 C24 H24A . . 109.4 ?
C25 C24 H24B . . 109.4 ?
C23 C24 H24B . . 109.4 ?
H24A C24 H24B . . 108.0 ?
N21 C25 C24 . . 110.20(11) ?
N21 C25 H25A . . 109.6 ?
C24 C25 H25A . . 109.6 ?
N21 C25 H25B . . 109.6 ?
C24 C25 H25B . . 109.6 ?
H25A C25 H25B . . 108.1 ?
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 C1 . 1.2229(16) ?
N11 C1 . 1.3825(15) ?
N11 C15 . 1.4661(15) ?
N11 C11 . 1.4736(15) ?
N21 C1 . 1.3839(15) ?
N21 C21 . 1.4604(16) ?
N21 C25 . 1.4639(15) ?
C11 C12 . 1.5178(18) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.5222(18) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.5273(19) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.5182(19) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C21 C22 . 1.5167(19) ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C22 C23 . 1.525(2) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 C24 . 1.526(2) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 C25 . 1.5193(19) ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C25 H25A . 0.9900 ?
C25 H25B . 0.9900 ?
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
C22 H22A O1 1_455 0.99 2.50 3.4110(17) 154
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
C15 N11 C1 O1 . . . . 5.50(17) ?
C11 N11 C1 O1 . . . . -133.79(13) ?
C15 N11 C1 N21 . . . . -175.32(10) ?
C11 N11 C1 N21 . . . . 45.39(15) ?
C21 N21 C1 O1 . . . . 4.47(18) ?
C25 N21 C1 O1 . . . . -137.93(13) ?
C21 N21 C1 N11 . . . . -174.72(11) ?
C25 N21 C1 N11 . . . . 42.88(16) ?
C1 N11 C11 C12 . . . . -160.27(11) ?
C15 N11 C11 C12 . . . . 59.21(14) ?
N11 C11 C12 C13 . . . . -55.74(14) ?
C11 C12 C13 C14 . . . . 53.25(14) ?
C12 C13 C14 C15 . . . . -53.49(14) ?
C1 N11 C15 C14 . . . . 158.70(10) ?
C11 N11 C15 C14 . . . . -59.06(13) ?
C13 C14 C15 N11 . . . . 55.89(14) ?
C1 N21 C21 C22 . . . . 154.25(11) ?
C25 N21 C21 C22 . . . . -60.21(15) ?
N21 C21 C22 C23 . . . . 55.64(16) ?
C21 C22 C23 C24 . . . . -52.35(17) ?
C22 C23 C24 C25 . . . . 52.16(17) ?
C1 N21 C25 C24 . . . . -155.95(11) ?
C21 N21 C25 C24 . . . . 60.33(15) ?
C23 C24 C25 N21 . . . . -55.55(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20200
