#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/29/7102991.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7102991
loop_
_publ_author_name
'Vardelle, Emilie'
'Gamba-Sanchez, Diego'
'Martin-Mingot, Agnès'
'Jouannetaud, Marie-Paule'
'Thibaudeau, Sébastien'
'Marrot, Jérôme'
_publ_section_title
;
 Cyclisation/fluorination of nitrogen containing dienes in superacid
 HF-SbF5: a new route to 3- and 4-fluoropiperidines.
;
_journal_issue                   12
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1473
_journal_page_last               1475
_journal_paper_doi               10.1039/b719309b
_journal_year                    2008
_chemical_formula_sum            'C13 H17 F N2 O2'
_chemical_formula_weight         252.29
_chemical_name_systematic
;
?
;
_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                96.205(7)
_cell_angle_beta                 93.734(8)
_cell_angle_gamma                103.868(7)
_cell_formula_units_Z            2
_cell_length_a                   6.3802(11)
_cell_length_b                   7.2136(11)
_cell_length_c                   14.245(3)
_cell_measurement_reflns_used    8571
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      3.30
_cell_volume                     629.95(19)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512x512
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26662
_diffrn_reflns_theta_full        30.08
_diffrn_reflns_theta_max         30.08
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.9763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0380
_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)+(0.0712P)²+0.1435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                2993
_reflns_number_total             3642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b719309b.txt
_cod_data_source_block           2e
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7102991
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.26809(11) 0.68588(10) 0.48066(5) 0.02296(17) Uani 1 1 d . . .
N1 N 1.01914(14) 0.37072(12) 0.27679(6) 0.01575(19) Uani 1 1 d . . .
C2 C 0.97053(17) 0.55594(14) 0.30773(8) 0.0177(2) Uani 1 1 d . . .
H2A H 0.9038 0.5492 0.3685 0.021 Uiso 1 1 calc R . .
H2B H 0.8657 0.5827 0.2599 0.021 Uiso 1 1 calc R . .
C3 C 1.17775(18) 0.71801(15) 0.32040(8) 0.0189(2) Uani 1 1 d . . .
H3A H 1.2356 0.7328 0.2581 0.023 Uiso 1 1 calc R . .
H3B H 1.1433 0.8403 0.3442 0.023 Uiso 1 1 calc R . .
C2' C 1.16329(17) 0.32607(14) 0.35110(7) 0.0168(2) Uani 1 1 d . . .
H2'1 H 1.1882 0.1972 0.3330 0.020 Uiso 1 1 calc R . .
H2'2 H 1.0948 0.3244 0.4115 0.020 Uiso 1 1 calc R . .
C3' C 1.37850(17) 0.47743(15) 0.36401(7) 0.0175(2) Uani 1 1 d . . .
H3'1 H 1.4739 0.4480 0.4149 0.021 Uiso 1 1 calc R . .
H3'2 H 1.4504 0.4718 0.3046 0.021 Uiso 1 1 calc R . .
C4 C 1.35007(17) 0.67947(15) 0.38917(7) 0.0172(2) Uani 1 1 d . . .
C5 C 0.81961(17) 0.21750(15) 0.25684(8) 0.0184(2) Uani 1 1 d . . .
H5A H 0.7290 0.2243 0.3103 0.022 Uiso 1 1 calc R . .
H5B H 0.8567 0.0914 0.2522 0.022 Uiso 1 1 calc R . .
C6 C 0.68959(17) 0.23005(14) 0.16591(7) 0.0163(2) Uani 1 1 d . . .
C7 C 0.46479(17) 0.15693(15) 0.15642(7) 0.0176(2) Uani 1 1 d . . .
H7 H 0.3950 0.1046 0.2080 0.021 Uiso 1 1 calc R . .
C8 C 0.34155(16) 0.15955(14) 0.07251(8) 0.0174(2) Uani 1 1 d . . .
H8 H 0.1886 0.1101 0.0662 0.021 Uiso 1 1 calc R . .
C7' C 0.79080(16) 0.30608(15) 0.08945(8) 0.0176(2) Uani 1 1 d . . .
H7' H 0.9436 0.3564 0.0955 0.021 Uiso 1 1 calc R . .
C8' C 0.67150(17) 0.30916(14) 0.00501(7) 0.0171(2) Uani 1 1 d . . .
H8' H 0.7406 0.3598 -0.0471 0.020 Uiso 1 1 calc R . .
C9 C 0.44786(16) 0.23609(14) -0.00142(7) 0.0157(2) Uani 1 1 d . . .
C10 C 1.56253(19) 0.83176(17) 0.39911(8) 0.0233(2) Uani 1 1 d . . .
H10A H 1.5359 0.9588 0.4164 0.035 Uiso 1 1 calc R . .
H10B H 1.6277 0.8296 0.3387 0.035 Uiso 1 1 calc R . .
H10C H 1.6615 0.8055 0.4486 0.035 Uiso 1 1 calc R . .
N2 N 0.32037(15) 0.23718(13) -0.09101(6) 0.01803(19) Uani 1 1 d . . .
O1 O 0.12101(13) 0.18341(13) -0.09464(6) 0.0262(2) Uani 1 1 d . . .
O2 O 0.41744(14) 0.29120(13) -0.15847(6) 0.0257(2) Uani 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C2' 110.43(8) . . ?
C5 N1 C2 110.63(8) . . ?
C2' N1 C2 109.18(8) . . ?
N1 C2 C3 110.30(8) . . ?
N1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 112.02(9) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N1 C2' C3' 109.51(8) . . ?
N1 C2' H2'1 109.8 . . ?
C3' C2' H2'1 109.8 . . ?
N1 C2' H2'2 109.8 . . ?
C3' C2' H2'2 109.8 . . ?
H2'1 C2' H2'2 108.2 . . ?
C4 C3' C2' 112.23(9) . . ?
C4 C3' H3'1 109.2 . . ?
C2' C3' H3'1 109.2 . . ?
C4 C3' H3'2 109.2 . . ?
C2' C3' H3'2 109.2 . . ?
H3'1 C3' H3'2 107.9 . . ?
F1 C4 C10 106.48(8) . . ?
F1 C4 C3' 106.91(8) . . ?
C10 C4 C3' 112.64(9) . . ?
F1 C4 C3 106.40(8) . . ?
C10 C4 C3 113.45(9) . . ?
C3' C4 C3 110.46(8) . . ?
N1 C5 C6 112.79(8) . . ?
N1 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
N1 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C7' 119.05(9) . . ?
C7 C6 C5 119.52(9) . . ?
C7' C6 C5 121.38(9) . . ?
C8 C7 C6 120.97(10) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C7 118.18(9) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8' C7' C6 120.99(9) . . ?
C8' C7' H7' 119.5 . . ?
C6 C7' H7' 119.5 . . ?
C7' C8' C9 118.21(9) . . ?
C7' C8' H8' 120.9 . . ?
C9 C8' H8' 120.9 . . ?
C8 C9 C8' 122.59(9) . . ?
C8 C9 N2 118.84(9) . . ?
C8' C9 N2 118.56(9) . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 N2 O1 123.23(9) . . ?
O2 N2 C9 118.36(9) . . ?
O1 N2 C9 118.40(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C4 1.4358(12) . ?
N1 C5 1.4607(13) . ?
N1 C2' 1.4693(13) . ?
N1 C2 1.4713(13) . ?
C2 C3 1.5263(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5202(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2' C3' 1.5219(14) . ?
C2' H2'1 0.9900 . ?
C2' H2'2 0.9900 . ?
C3' C4 1.5192(14) . ?
C3' H3'1 0.9900 . ?
C3' H3'2 0.9900 . ?
C4 C10 1.5139(15) . ?
C5 C6 1.5152(14) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.3965(14) . ?
C6 C7' 1.3982(15) . ?
C7 C8 1.3917(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.3832(15) . ?
C8 H8 0.9500 . ?
C7' C8' 1.3861(15) . ?
C7' H7' 0.9500 . ?
C8' C9 1.3908(14) . ?
C8' H8' 0.9500 . ?
C9 N2 1.4699(13) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N2 O2 1.2255(13) . ?
N2 O1 1.2335(12) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21118623
