#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/29/1502979.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_1502979
loop_
_publ_author_name
'Knoll, Wolfgang'
'Mieusset, Jean-Luc'
'Arion, Vladimir B.'
'Brecker, Lothar'
'Brinker, Udo H.'
_publ_section_title
;
 2H-Azirines from a concerted addition of alkylcarbenes to nitrile groups.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2366
_journal_page_last               2369
_journal_paper_doi               10.1021/ol100703r
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C10 H13 F N2'
_chemical_formula_sum            'C10 H13 F N2'
_chemical_formula_weight         180.22
_chemical_name_systematic
; 
4-Azi-1-fluoroadamantane 
;
_space_group_IT_number           106
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4c -2ab'
_symmetry_space_group_name_H-M   'P 42 b c'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.0215(4)
_cell_length_b                   14.0215(4)
_cell_length_c                   8.8612(3)
_cell_measurement_reflns_used    7503
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.30
_cell_measurement_theta_min      3.60
_cell_volume                     1742.13(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0116
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            68494
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1068
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0298
_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)+(0.0521P)²+0.3802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                970
_reflns_number_total             1068
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100703r_si_002.cif
_cod_data_source_block           wokn002
_cod_original_sg_symbol_H-M      P42bc
_cod_database_code               1502979
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z+1/2'
'y, -x, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'
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
F1X F 0.9269(2) 0.0081(3) 0.0288(4) 0.0217(7) Uani 0.30 1 d PD A 1
F1 F 0.77816(10) 0.19678(10) 0.39622(17) 0.0208(3) Uani 0.70 1 d PD B 2
N1 N 0.61392(12) -0.13713(11) 0.1689(2) 0.0313(4) Uani 1 1 d . . .
N2 N 0.57379(11) -0.08895(12) 0.2679(2) 0.0309(4) Uani 1 1 d . . .
C3 C 0.68067(12) 0.12388(12) 0.2133(2) 0.0176(3) Uani 1 1 d . B .
H3A H 0.6857 0.1812 0.1485 0.021 Uiso 1 1 calc R . .
H3B H 0.6238 0.1309 0.2785 0.021 Uiso 1 1 calc R . .
C5 C 0.76235(12) 0.02781(11) 0.41442(19) 0.0166(4) Uani 1 1 d . B .
H5A H 0.7058 0.0344 0.4805 0.020 Uiso 1 1 calc R . .
H5B H 0.8197 0.0235 0.4792 0.020 Uiso 1 1 calc R . .
C4 C 0.77008(12) 0.11425(12) 0.31055(19) 0.0159(4) Uani 1 1 d D . .
H4A H 0.7760 0.1704 0.3717 0.019 Uiso 0.30 1 d PR B .
C2 C 0.67088(12) 0.03416(12) 0.1147(2) 0.0163(3) Uani 1 1 d . . .
H2 H 0.6118 0.0378 0.0518 0.024 Uiso 1 1 calc R B .
C8 C 0.85848(12) 0.10602(12) 0.2114(2) 0.0179(3) Uani 1 1 d . A .
H8A H 0.9163 0.1014 0.2750 0.021 Uiso 1 1 calc R . .
H8B H 0.8644 0.1631 0.1464 0.021 Uiso 1 1 calc R . .
C6 C 0.75326(12) -0.06299(12) 0.31753(18) 0.0160(4) Uani 1 1 d . . .
H6 H 0.7464 -0.1207 0.3830 0.024 Uiso 1 1 calc R B .
C7 C 0.84150(12) -0.07217(12) 0.2146(2) 0.0186(4) Uani 1 1 d . A .
H7A H 0.8998 -0.0780 0.2769 0.022 Uiso 1 1 calc R . .
H7B H 0.8359 -0.1301 0.1514 0.022 Uiso 1 1 calc R . .
C1 C 0.66733(12) -0.05145(12) 0.2168(2) 0.0176(4) Uani 1 1 d . B .
C9 C 0.75977(12) 0.02428(13) 0.0131(2) 0.0183(4) Uani 1 1 d . A .
H9A H 0.7539 -0.0332 -0.0511 0.022 Uiso 1 1 calc R . .
H9B H 0.7654 0.0806 -0.0536 0.022 Uiso 1 1 calc R . .
C10 C 0.84851(11) 0.01624(12) 0.1137(2) 0.0173(3) Uani 1 1 d D . .
H10A H 0.9039 0.0105 0.0506 0.021 Uiso 0.70 1 d PR A .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0000 '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
N2 N1 C1 65.46(13)
N1 N2 C1 64.96(13)
C4 C3 C2 108.76(13)
C4 C3 H3A 109.9
C2 C3 H3A 109.9
C4 C3 H3B 109.9
C2 C3 H3B 109.9
H3A C3 H3B 108.3
C4 C5 C6 109.04(14)
C4 C5 H5A 109.9
C6 C5 H5A 109.9
C4 C5 H5B 109.9
C6 C5 H5B 109.9
H5A C5 H5B 108.3
F1 C4 C8 108.18(14)
F1 C4 C5 109.76(14)
C8 C4 C5 110.21(13)
F1 C4 C3 107.57(13)
C8 C4 C3 110.42(15)
C5 C4 C3 110.63(13)
C8 C4 H4A 108.5
C5 C4 H4A 108.5
C3 C4 H4A 108.5
C1 C2 C3 108.28(15)
C1 C2 C9 107.82(14)
C3 C2 C9 109.43(14)
C1 C2 H2 110.4
C3 C2 H2 110.4
C9 C2 H2 110.4
C4 C8 C10 108.27(13)
C4 C8 H8A 110.0
C10 C8 H8A 110.0
C4 C8 H8B 110.0
C10 C8 H8B 110.0
H8A C8 H8B 108.4
C1 C6 C5 107.89(13)
C1 C6 C7 107.45(14)
C5 C6 C7 109.40(14)
C1 C6 H6 110.7
C5 C6 H6 110.7
C7 C6 H6 110.7
C10 C7 C6 109.22(13)
C10 C7 H7A 109.8
C6 C7 H7A 109.8
C10 C7 H7B 109.8
C6 C7 H7B 109.8
H7A C7 H7B 108.3
N1 C1 N2 49.58(11)
N1 C1 C2 119.51(16)
N2 C1 C2 119.71(15)
N1 C1 C6 119.18(15)
N2 C1 C6 119.18(16)
C2 C1 C6 114.54(14)
C10 C9 C2 108.81(15)
C10 C9 H9A 109.9
C2 C9 H9A 109.9
C10 C9 H9B 109.9
C2 C9 H9B 109.9
H9A C9 H9B 108.3
F1X C10 C7 108.21(19)
F1X C10 C8 108.2(2)
C7 C10 C8 109.89(14)
F1X C10 C9 110.3(2)
C7 C10 C9 110.28(13)
C8 C10 C9 109.97(13)
C7 C10 H10A 108.9
C8 C10 H10A 108.9
C9 C10 H10A 108.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1X C10 1.336(3)
F1X H10A 0.3773
F1 C4 1.389(2)
F1 H4A 0.4294
N1 N2 1.242(3)
N1 C1 1.478(2)
N2 C1 1.484(2)
C3 C4 1.528(2)
C3 C2 1.538(2)
C3 H3A 0.9900
C3 H3B 0.9900
C5 C4 1.526(2)
C5 C6 1.541(2)
C5 H5A 0.9900
C5 H5B 0.9900
C4 C8 1.524(2)
C4 H4A 0.9599
C2 C1 1.504(2)
C2 C9 1.544(2)
C2 H2 1.0000
C8 C10 1.534(2)
C8 H8A 0.9900
C8 H8B 0.9900
C6 C1 1.508(2)
C6 C7 1.543(2)
C6 H6 1.0000
C7 C10 1.532(2)
C7 H7A 0.9900
C7 H7B 0.9900
C9 C10 1.535(2)
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9600
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
C6 C5 C4 F1 179.90(14)
C6 C5 C4 C8 -61.06(17)
C6 C5 C4 C3 61.35(18)
C2 C3 C4 F1 178.92(14)
C2 C3 C4 C8 61.07(18)
C2 C3 C4 C5 -61.21(19)
C4 C3 C2 C1 57.43(19)
C4 C3 C2 C9 -59.85(18)
F1 C4 C8 C10 -178.56(14)
C5 C4 C8 C10 61.44(18)
C3 C4 C8 C10 -61.09(17)
C4 C5 C6 C1 -57.33(18)
C4 C5 C6 C7 59.26(18)
C1 C6 C7 C10 57.81(17)
C5 C6 C7 C10 -59.06(18)
N2 N1 C1 C2 -105.43(18)
N2 N1 C1 C6 104.95(18)
N1 N2 C1 C2 105.01(18)
N1 N2 C1 C6 -104.94(18)
C3 C2 C1 N1 150.44(15)
C9 C2 C1 N1 -91.25(19)
C3 C2 C1 N2 92.77(19)
C9 C2 C1 N2 -148.91(17)
C3 C2 C1 C6 -58.60(19)
C9 C2 C1 C6 59.72(18)
C5 C6 C1 N1 -150.59(16)
C7 C6 C1 N1 91.56(19)
C5 C6 C1 N2 -93.18(18)
C7 C6 C1 N2 148.96(15)
C5 C6 C1 C2 58.35(19)
C7 C6 C1 C2 -59.51(18)
C1 C2 C9 C10 -57.81(17)
C3 C2 C9 C10 59.76(17)
C6 C7 C10 F1X 178.2(2)
C6 C7 C10 C8 60.21(17)
C6 C7 C10 C9 -61.18(18)
C4 C8 C10 F1X -178.85(19)
C4 C8 C10 C7 -60.90(17)
C4 C8 C10 C9 60.67(18)
C2 C9 C10 F1X -179.6(2)
C2 C9 C10 C7 60.93(17)
C2 C9 C10 C8 -60.41(17)
