#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/29/7102992.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_7102992
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 H15 F N2 O3'
_chemical_formula_weight         266.27
_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                79.479(2)
_cell_angle_beta                 80.510(2)
_cell_angle_gamma                78.922(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6927(3)
_cell_length_b                   8.2566(3)
_cell_length_c                   12.1565(5)
_cell_measurement_reflns_used    5746
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.88
_cell_measurement_theta_min      2.74
_cell_volume                     642.26(5)
_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      293(2)
_diffrn_detector_area_resol_mean 512x512
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13438
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0366
_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)+(0.0777P)²+0.0821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1315
_reflns_number_gt                1917
_reflns_number_total             2260
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b719309b.txt
_cod_data_source_block           2j
_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               7102992
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 0.11822(17) -0.04181(12) 0.81230(8) 0.0633(3) Uani 1 1 d . . .
N1 N 0.05269(18) 0.20028(16) 0.55588(10) 0.0436(3) Uani 1 1 d . . .
C2 C 0.2379(2) 0.0798(2) 0.57740(13) 0.0468(4) Uani 1 1 d . . .
H2A H 0.3395 0.0864 0.5106 0.056 Uiso 1 1 calc R . .
H2B H 0.2051 -0.0323 0.5936 0.056 Uiso 1 1 calc R . .
C3 C 0.3257(3) 0.1141(2) 0.67572(15) 0.0542(4) Uani 1 1 d . . .
H3A H 0.3771 0.2191 0.6548 0.065 Uiso 1 1 calc R . .
H3B H 0.4406 0.0265 0.6927 0.065 Uiso 1 1 calc R . .
C2' C -0.1074(2) 0.2005(2) 0.65366(14) 0.0541(5) Uani 1 1 d . . .
H2'A H -0.1520 0.0925 0.6720 0.065 Uiso 1 1 calc R . .
H2'B H -0.2250 0.2846 0.6357 0.065 Uiso 1 1 calc R . .
C3' C -0.0272(3) 0.2366(2) 0.75366(15) 0.0647(5) Uani 1 1 d . . .
H3'A H -0.0031 0.3513 0.7388 0.078 Uiso 1 1 calc R . .
H3'B H -0.1310 0.2258 0.8192 0.078 Uiso 1 1 calc R . .
C4 C 0.1685(3) 0.1225(2) 0.78018(14) 0.0539(4) Uani 1 1 d . . .
C5 C 0.0211(2) 0.30295(18) 0.45859(12) 0.0382(4) Uani 1 1 d . . .
C6 C 0.1959(2) 0.30992(17) 0.36354(12) 0.0367(3) Uani 1 1 d . . .
C7 C 0.1627(2) 0.28017(19) 0.25984(12) 0.0427(4) Uani 1 1 d . . .
H7 H 0.0389 0.2504 0.2528 0.051 Uiso 1 1 calc R . .
C8 C 0.3117(2) 0.2943(2) 0.16702(12) 0.0455(4) Uani 1 1 d . . .
H8 H 0.2906 0.2726 0.0978 0.055 Uiso 1 1 calc R . .
C7' C 0.3797(2) 0.35830(18) 0.37301(12) 0.0401(4) Uani 1 1 d . . .
H7' H 0.4023 0.3794 0.4421 0.048 Uiso 1 1 calc R . .
C8' C 0.5286(2) 0.37516(19) 0.28045(12) 0.0413(4) Uani 1 1 d . . .
H8' H 0.6510 0.4086 0.2862 0.050 Uiso 1 1 calc R . .
C9 C 0.4920(2) 0.34133(18) 0.17941(12) 0.0404(4) Uani 1 1 d . . .
C10 C 0.2513(5) 0.1558(3) 0.8805(2) 0.0953(8) Uani 1 1 d . . .
H10A H 0.1489 0.1474 0.9457 0.143 Uiso 1 1 calc R . .
H10B H 0.2858 0.2661 0.8651 0.143 Uiso 1 1 calc R . .
H10C H 0.3719 0.0752 0.8945 0.143 Uiso 1 1 calc R . .
N2 N 0.6512(2) 0.35545(18) 0.08091(11) 0.0510(4) Uani 1 1 d . . .
O1 O 0.6237(2) 0.3103(2) -0.00446(10) 0.0724(4) Uani 1 1 d . . .
O2 O 0.8022(2) 0.41221(19) 0.08888(11) 0.0707(4) Uani 1 1 d . . .
O3 O -0.14539(16) 0.39021(15) 0.44368(9) 0.0524(3) 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 126.47(12) . . ?
C5 N1 C2' 120.59(12) . . ?
C2 N1 C2' 112.94(12) . . ?
N1 C2 C3 110.77(13) . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C2 C3 C4 112.34(14) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
N1 C2' C3' 110.32(14) . . ?
N1 C2' H2'A 109.6 . . ?
C3' C2' H2'A 109.6 . . ?
N1 C2' H2'B 109.6 . . ?
C3' C2' H2'B 109.6 . . ?
H2'A C2' H2'B 108.1 . . ?
C4 C3' C2' 113.20(14) . . ?
C4 C3' H3'A 108.9 . . ?
C2' C3' H3'A 108.9 . . ?
C4 C3' H3'B 108.9 . . ?
C2' C3' H3'B 108.9 . . ?
H3'A C3' H3'B 107.8 . . ?
F1 C4 C3' 106.29(15) . . ?
F1 C4 C10 105.05(15) . . ?
C3' C4 C10 114.17(17) . . ?
F1 C4 C3 105.46(13) . . ?
C3' C4 C3 111.19(14) . . ?
C10 C4 C3 113.79(18) . . ?
O3 C5 N1 122.64(13) . . ?
O3 C5 C6 118.47(13) . . ?
N1 C5 C6 118.89(12) . . ?
C7 C6 C7' 119.41(13) . . ?
C7 C6 C5 117.48(13) . . ?
C7' C6 C5 122.88(12) . . ?
C8 C7 C6 120.71(14) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 118.41(13) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8' C7' C6 120.42(13) . . ?
C8' C7' H7' 119.8 . . ?
C6 C7' H7' 119.8 . . ?
C9 C8' C7' 118.55(13) . . ?
C9 C8' H8' 120.7 . . ?
C7' C8' H8' 120.7 . . ?
C8 C9 C8' 122.48(14) . . ?
C8 C9 N2 118.48(13) . . ?
C8' C9 N2 119.04(14) . . ?
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 . . ?
O1 N2 O2 123.68(14) . . ?
O1 N2 C9 117.91(14) . . ?
O2 N2 C9 118.41(14) . . ?
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 1.4301(19) . ?
N1 C5 1.3451(19) . ?
N1 C2 1.4603(19) . ?
N1 C2' 1.4632(19) . ?
C2 C3 1.507(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.513(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2' C3' 1.505(3) . ?
C2' H2'A 0.9700 . ?
C2' H2'B 0.9700 . ?
C3' C4 1.503(3) . ?
C3' H3'A 0.9700 . ?
C3' H3'B 0.9700 . ?
C4 C10 1.508(3) . ?
C5 O3 1.2266(17) . ?
C5 C6 1.504(2) . ?
C6 C7 1.387(2) . ?
C6 C7' 1.392(2) . ?
C7 C8 1.381(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.375(2) . ?
C8 H8 0.9300 . ?
C7' C8' 1.380(2) . ?
C7' H7' 0.9300 . ?
C8' C9 1.378(2) . ?
C8' H8' 0.9300 . ?
C9 N2 1.469(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N2 O1 1.2167(19) . ?
N2 O2 1.2172(19) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21118622
