#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/08/2230815.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_2230815
loop_
_publ_author_name
'Yadav, Vitthal N.'
'Hansen, Tore'
'Görbitz, Carl Henrik'
_publ_section_title
;
 1,1'-(4,4'-Bipiperidine-1,1'-diyl)bis(2,2,2-trifluoroethanone)
;
_journal_coeditor_code           NG5179
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1691
_journal_paper_doi               10.1107/S1600536811022434
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H18 F6 N2 O2'
_chemical_formula_moiety         'C14 H18 F6 N2 O2'
_chemical_formula_sum            'C14 H18 F6 N2 O2'
_chemical_formula_weight         360.30
_chemical_melting_point          397
_chemical_name_common            N,N'-di-trifluoroacetyl-4,4'-bipiperidine
_chemical_name_systematic
;
1,1'-(4,4'-Bipiperidine-1,1'-diyl)bis(2,2,2-trifluoroethanone)
;
_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                99.952(2)
_cell_angle_beta                 108.564(2)
_cell_angle_gamma                101.542(2)
_cell_formula_units_Z            1
_cell_length_a                   6.6825(12)
_cell_length_b                   6.7350(12)
_cell_length_c                   9.3089(16)
_cell_measurement_reflns_used    2545
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.3867
_cell_volume                     376.30(12)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      105(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method
'Sets of exposures each taken over 0.5° ω rotation'
_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  0.0092
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3303
_diffrn_reflns_theta_full        25.67
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.9617
_exptl_absorpt_correction_T_min  0.9208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rods
_exptl_crystal_F_000             186
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0398P)²+0.1258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0795
_reflns_number_gt                1586
_reflns_number_total             1731
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng5179.cif
_cod_data_source_block           I
_cod_database_code               2230815
_cod_database_fobs_code          2230815
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
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.11060(12) 0.31663(10) 0.84127(9) 0.03113(19) Uani d . 1 1 . .
F F2 0.00855(11) 0.51373(11) 0.68885(8) 0.02834(18) Uani d . 1 1 . .
F F3 0.13374(10) 0.63747(10) 0.93992(7) 0.02236(16) Uani d . 1 1 . .
O O1 0.49112(14) 0.43556(12) 0.82275(10) 0.02475(19) Uani d . 1 1 . .
N N1 0.47091(14) 0.76768(13) 0.81595(10) 0.01700(19) Uani d . 1 1 . .
C C2 0.68525(17) 0.82626(17) 0.80093(12) 0.0199(2) Uani d . 1 1 . .
H H21 0.7640 0.7193 0.8255 0.024 Uiso calc R 1 1 . .
H H22 0.7745 0.9622 0.8764 0.024 Uiso calc R 1 1 . .
C C3 0.65544(17) 0.84357(16) 0.63442(12) 0.0186(2) Uani d . 1 1 . .
H H31 0.5798 0.7036 0.5607 0.022 Uiso calc R 1 1 . .
H H32 0.8014 0.8906 0.6274 0.022 Uiso calc R 1 1 . .
C C4 0.52192(16) 0.99793(15) 0.58605(11) 0.0155(2) Uani d . 1 1 . .
H H41 0.6099 1.1413 0.6534 0.019 Uiso calc R 1 1 . .
C C5 0.30751(16) 0.94359(15) 0.61687(11) 0.0166(2) Uani d . 1 1 . .
H H51 0.2321 1.0545 0.5987 0.020 Uiso calc R 1 1 . .
H H52 0.2099 0.8101 0.5418 0.020 Uiso calc R 1 1 . .
C C6 0.34705(17) 0.92258(15) 0.78370(12) 0.0171(2) Uani d . 1 1 . .
H H61 0.4304 1.0600 0.8592 0.021 Uiso calc R 1 1 . .
H H62 0.2047 0.8779 0.7965 0.021 Uiso calc R 1 1 . .
C C7 0.39316(17) 0.57031(16) 0.82058(11) 0.0176(2) Uani d . 1 1 . .
C C8 0.15978(18) 0.51030(16) 0.82412(13) 0.0210(2) Uani d . 1 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
F1 0.0357(4) 0.0179(3) 0.0457(4) 0.0046(3) 0.0226(3) 0.0114(3)
F2 0.0223(3) 0.0307(4) 0.0252(3) 0.0026(3) 0.0040(3) 0.0043(3)
F3 0.0247(3) 0.0240(3) 0.0250(3) 0.0098(3) 0.0148(3) 0.0082(3)
O1 0.0318(4) 0.0201(4) 0.0305(4) 0.0140(3) 0.0164(4) 0.0093(3)
N1 0.0180(4) 0.0177(4) 0.0194(4) 0.0078(3) 0.0087(3) 0.0080(3)
C2 0.0169(5) 0.0246(5) 0.0218(5) 0.0080(4) 0.0078(4) 0.0110(4)
C3 0.0184(5) 0.0217(5) 0.0207(5) 0.0093(4) 0.0093(4) 0.0095(4)
C4 0.0164(4) 0.0152(4) 0.0163(5) 0.0055(4) 0.0065(4) 0.0052(4)
C5 0.0175(5) 0.0175(4) 0.0174(5) 0.0073(4) 0.0072(4) 0.0063(4)
C6 0.0211(5) 0.0160(4) 0.0185(5) 0.0090(4) 0.0093(4) 0.0065(4)
C7 0.0218(5) 0.0174(5) 0.0157(4) 0.0070(4) 0.0086(4) 0.0043(4)
C8 0.0238(5) 0.0171(5) 0.0233(5) 0.0053(4) 0.0103(4) 0.0058(4)
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'
F F 0.0171 0.0103 '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
C7 N1 C2 . . 118.28(8) ?
C7 N1 C6 . . 127.41(9) ?
C2 N1 C6 . . 112.38(8) ?
N1 C2 C3 . . 110.03(8) ?
N1 C2 H21 . . 109.7 ?
C3 C2 H21 . . 109.7 ?
N1 C2 H22 . . 109.7 ?
C3 C2 H22 . . 109.7 ?
H21 C2 H22 . . 108.2 ?
C2 C3 C4 . . 111.99(8) ?
C2 C3 H31 . . 109.2 ?
C4 C3 H31 . . 109.2 ?
C2 C3 H32 . . 109.2 ?
C4 C3 H32 . . 109.2 ?
H31 C3 H32 . . 107.9 ?
C5 C4 C3 . . 109.77(8) ?
C5 C4 C4 . 2_676 111.59(10) ?
C3 C4 C4 . 2_676 111.60(10) ?
C5 C4 H41 . . 107.9 ?
C3 C4 H41 . . 107.9 ?
C4 C4 H41 2_676 . 107.9 ?
C6 C5 C4 . . 112.24(8) ?
C6 C5 H51 . . 109.2 ?
C4 C5 H51 . . 109.2 ?
C6 C5 H52 . . 109.2 ?
C4 C5 H52 . . 109.2 ?
H51 C5 H52 . . 107.9 ?
N1 C6 C5 . . 109.91(8) ?
N1 C6 H61 . . 109.7 ?
C5 C6 H61 . . 109.7 ?
N1 C6 H62 . . 109.7 ?
C5 C6 H62 . . 109.7 ?
H61 C6 H62 . . 108.2 ?
O1 C7 N1 . . 125.64(10) ?
O1 C7 C8 . . 117.66(9) ?
N1 C7 C8 . . 116.70(9) ?
F1 C8 F3 . . 107.55(8) ?
F1 C8 F2 . . 107.07(9) ?
F3 C8 F2 . . 107.07(9) ?
F1 C8 C7 . . 110.32(9) ?
F3 C8 C7 . . 113.47(9) ?
F2 C8 C7 . . 111.08(8) ?
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
F1 C8 . 1.3299(12) ?
F2 C8 . 1.3478(13) ?
F3 C8 . 1.3363(12) ?
O1 C7 . 1.2199(13) ?
N1 C7 . 1.3403(13) ?
N1 C2 . 1.4654(13) ?
N1 C6 . 1.4694(12) ?
C2 C3 . 1.5267(14) ?
C2 H21 . 0.9900 ?
C2 H22 . 0.9900 ?
C3 C4 . 1.5352(13) ?
C3 H31 . 0.9900 ?
C3 H32 . 0.9900 ?
C4 C5 . 1.5354(14) ?
C4 C4 2_676 1.5404(19) ?
C4 H41 . 1.0000 ?
C5 C6 . 1.5268(13) ?
C5 H51 . 0.9900 ?
C5 H52 . 0.9900 ?
C6 H61 . 0.9900 ?
C6 H62 . 0.9900 ?
C7 C8 . 1.5433(15) ?
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
C7 N1 C2 C3 . . . . 104.98(10) ?
C6 N1 C2 C3 . . . . -60.38(11) ?
N1 C2 C3 C4 . . . . 55.87(11) ?
C2 C3 C4 C5 . . . . -51.51(11) ?
C2 C3 C4 C4 . . . 2_676 -175.77(10) ?
C3 C4 C5 C6 . . . . 51.41(11) ?
C4 C4 C5 C6 2_676 . . . 175.67(9) ?
C7 N1 C6 C5 . . . . -103.67(11) ?
C2 N1 C6 C5 . . . . 60.06(11) ?
C4 C5 C6 N1 . . . . -55.39(11) ?
C2 N1 C7 O1 . . . . 4.65(15) ?
C6 N1 C7 O1 . . . . 167.54(10) ?
C2 N1 C7 C8 . . . . -175.62(8) ?
C6 N1 C7 C8 . . . . -12.72(15) ?
O1 C7 C8 F1 . . . . 4.75(13) ?
N1 C7 C8 F1 . . . . -175.01(8) ?
O1 C7 C8 F3 . . . . 125.51(10) ?
N1 C7 C8 F3 . . . . -54.25(12) ?
O1 C7 C8 F2 . . . . -113.81(10) ?
N1 C7 C8 F2 . . . . 66.43(12) ?
