#------------------------------------------------------------------------------
#$Date: 2016-03-26 12:56:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180217 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/03/7110380.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7110380
loop_
_publ_author_name
'Eric Banks, R.'
'Besheesh, Mohamed K.'
'Lawrence, Nicholas J.'
'Pritchard, Robin G.'
'Tovell, David J.'
_publ_section_title
;
 Novel conversion of perfluoro(2,6-dimethyl-1-azacyclohexene) to
 3,3,4,4,5-pentafluoro-2,6-diphenyl-2,6-bis(trifluoromethyl)-
 1-azabicyclo[3.1.0]hexane
;
_journal_issue                   1
_journal_name_full               'Chemical Communications'
_journal_page_first              47
_journal_paper_doi               10.1039/a807673a
_journal_year                    1999
_chemical_formula_sum            'C19 H11 F12 N'
_chemical_formula_weight         481.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                   27.339(2)
_cell_length_b                   8.3850(10)
_cell_length_c                   15.593(2)
_cell_measurement_temperature    203(2)
_cell_volume                     3574.5(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3129
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.9716
_exptl_absorpt_correction_T_min  0.9267
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0355
_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)+(0.0323P)²+1.5942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0808
_reflns_number_gt                2295
_reflns_number_total             3129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            807673asup1.cif
_cod_data_source_block           beta
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               7110380
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y, -z-1/2'
'x-1/2, y-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
N1 N 0.38082(7) 0.2214(2) 0.32397(12) 0.0226(4) Uani 1 1 d
C2 C 0.41641(8) 0.1508(3) 0.38296(13) 0.0248(5) Uani 1 1 d
C3 C 0.42647(8) -0.0240(3) 0.35631(14) 0.0287(5) Uani 1 1 d
C4 C 0.38223(8) -0.1201(3) 0.32543(15) 0.0307(5) Uani 1 1 d
C5 C 0.35047(8) -0.0286(3) 0.26105(14) 0.0274(5) Uani 1 1 d
C6 C 0.33810(7) 0.1457(2) 0.28526(13) 0.0231(5) Uani 1 1 d
C7 C 0.39931(8) 0.1614(3) 0.47783(14) 0.0331(6) Uani 1 1 d
C8 C 0.46270(8) 0.2552(3) 0.37853(13) 0.0251(5) Uani 1 1 d
C9 C 0.50931(8) 0.1941(3) 0.39105(15) 0.0333(6) Uani 1 1 d
C10 C 0.54936(9) 0.2930(3) 0.39173(16) 0.0378(6) Uani 1 1 d
C11 C 0.54405(9) 0.4542(3) 0.38045(17) 0.0415(6) Uani 1 1 d
C12 C 0.49817(10) 0.5164(3) 0.36956(19) 0.0451(7) Uani 1 1 d
C13 C 0.45782(9) 0.4185(3) 0.36889(16) 0.0354(6) Uani 1 1 d
C14 C 0.29266(8) 0.1562(3) 0.34456(14) 0.0289(5) Uani 1 1 d
C15 C 0.32432(7) 0.2455(3) 0.20562(13) 0.0233(5) Uani 1 1 d
C16 C 0.33103(8) 0.4094(3) 0.20786(14) 0.0262(5) Uani 1 1 d
C17 C 0.31905(8) 0.5026(3) 0.13797(15) 0.0315(5) Uani 1 1 d
C18 C 0.30024(9) 0.4331(3) 0.06486(15) 0.0343(6) Uani 1 1 d
C19 C 0.29201(9) 0.2716(3) 0.06323(15) 0.0369(6) Uani 1 1 d
C20 C 0.30371(8) 0.1783(3) 0.13303(15) 0.0308(5) Uani 1 1 d
F3A F 0.44839(5) -0.10794(16) 0.41981(9) 0.0405(4) Uani 1 1 d
F3B F 0.45757(4) -0.02261(16) 0.28879(8) 0.0355(3) Uani 1 1 d
F4A F 0.35509(5) -0.16998(16) 0.39167(9) 0.0418(4) Uani 1 1 d
F4B F 0.39864(5) -0.25346(15) 0.28656(9) 0.0425(4) Uani 1 1 d
F5A F 0.31014(5) -0.11723(15) 0.24552(9) 0.0391(3) Uani 1 1 d
F5B F 0.37718(5) -0.02660(15) 0.18762(8) 0.0341(3) Uani 1 1 d
F7A F 0.43687(5) 0.15236(18) 0.53167(8) 0.0423(4) Uani 1 1 d
F7B F 0.36871(6) 0.0480(2) 0.50172(8) 0.0545(4) Uani 1 1 d
F7C F 0.37774(6) 0.29990(18) 0.49225(8) 0.0511(4) Uani 1 1 d
F14A F 0.28847(5) 0.30205(16) 0.37650(9) 0.0413(4) Uani 1 1 d
F14B F 0.29337(5) 0.05687(18) 0.41066(9) 0.0455(4) Uani 1 1 d
F14C F 0.25199(5) 0.12487(18) 0.30191(8) 0.0433(4) Uani 1 1 d
H1 H 0.3951(8) 0.265(3) 0.2872(14) 0.024(7) Uiso 1 1 d
H9 H 0.5133(8) 0.092(3) 0.3992(14) 0.029(7) Uiso 1 1 d
H10 H 0.5808(10) 0.250(3) 0.4029(15) 0.041(7) Uiso 1 1 d
H11 H 0.5715(9) 0.523(3) 0.3816(16) 0.047(8) Uiso 1 1 d
H12 H 0.4925(10) 0.626(3) 0.3602(18) 0.064(9) Uiso 1 1 d
H13 H 0.4270(8) 0.464(3) 0.3640(14) 0.029(6) Uiso 1 1 d
H16 H 0.3429(7) 0.457(2) 0.2583(14) 0.024(6) Uiso 1 1 d
H17 H 0.3226(8) 0.615(3) 0.1406(15) 0.036(7) Uiso 1 1 d
H18 H 0.2924(8) 0.499(3) 0.0180(16) 0.041(7) Uiso 1 1 d
H19 H 0.2770(8) 0.220(3) 0.0130(15) 0.038(7) Uiso 1 1 d
H20 H 0.2975(8) 0.068(3) 0.1327(13) 0.025(6) Uiso 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'
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
C6 N1 C2 128.05(18)
N1 C2 C8 106.77(17)
N1 C2 C3 109.38(17)
C8 C2 C3 112.34(17)
N1 C2 C7 112.03(17)
C8 C2 C7 104.92(17)
C3 C2 C7 111.28(18)
F3B C3 F3A 107.18(17)
F3B C3 C4 104.84(17)
F3A C3 C4 107.83(18)
F3B C3 C2 108.18(17)
F3A C3 C2 111.99(18)
C4 C3 C2 116.25(18)
F4A C4 F4B 105.76(17)
F4A C4 C3 111.08(18)
F4B C4 C3 108.36(18)
F4A C4 C5 110.34(18)
F4B C4 C5 107.99(18)
C3 C4 C5 112.99(18)
F5A C5 F5B 107.13(17)
F5A C5 C4 107.74(17)
F5B C5 C4 104.69(17)
F5A C5 C6 112.64(17)
F5B C5 C6 108.14(16)
C4 C5 C6 115.88(18)
N1 C6 C15 107.01(17)
N1 C6 C5 109.67(17)
C15 C6 C5 111.64(17)
N1 C6 C14 111.70(17)
C15 C6 C14 104.68(16)
C5 C6 C14 111.96(17)
F7B C7 F7C 107.60(19)
F7B C7 F7A 105.67(19)
F7C C7 F7A 106.72(19)
F7B C7 C2 114.71(19)
F7C C7 C2 110.27(18)
F7A C7 C2 111.45(18)
C13 C8 C9 118.0(2)
C13 C8 C2 119.2(2)
C9 C8 C2 122.6(2)
C10 C9 C8 120.7(2)
C11 C10 C9 120.7(2)
C12 C11 C10 119.2(3)
C11 C12 C13 120.6(3)
C12 C13 C8 120.8(2)
F14C C14 F14B 106.19(18)
F14C C14 F14A 107.44(18)
F14B C14 F14A 106.79(18)
F14C C14 C6 111.25(17)
F14B C14 C6 114.60(18)
F14A C14 C6 110.21(18)
C20 C15 C16 118.5(2)
C20 C15 C6 122.4(2)
C16 C15 C6 118.96(19)
C17 C16 C15 120.6(2)
C18 C17 C16 120.1(2)
C19 C18 C17 119.5(2)
C18 C19 C20 120.5(2)
C19 C20 C15 120.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.460(3)
N1 C2 1.464(3)
C2 C8 1.540(3)
C2 C3 1.549(3)
C2 C7 1.554(3)
C3 F3B 1.353(2)
C3 F3A 1.354(2)
C3 C4 1.531(3)
C4 F4A 1.339(3)
C4 F4B 1.349(3)
C4 C5 1.533(3)
C5 F5A 1.351(2)
C5 F5B 1.358(2)
C5 C6 1.547(3)
C6 C15 1.544(3)
C6 C14 1.551(3)
C7 F7B 1.320(3)
C7 F7C 1.321(3)
C7 F7A 1.329(3)
C8 C13 1.384(3)
C8 C9 1.387(3)
C9 C10 1.374(3)
C10 C11 1.371(4)
C11 C12 1.369(4)
C12 C13 1.375(4)
C14 F14C 1.322(3)
C14 F14B 1.325(2)
C14 F14A 1.325(3)
C15 C20 1.384(3)
C15 C16 1.387(3)
C16 C17 1.381(3)
C17 C18 1.380(3)
C18 C19 1.373(4)
C19 C20 1.378(3)
