#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/92/2219278.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_2219278
loop_
_publ_author_name
'Parthiban, P.'
'Thirumurugan, K.'
'Ramkumar, V.'
'Pazhamalai, S.'
'Jeong, Yeon Tae'
_publ_section_title
;
 2,4-Bis(3-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-one
;
_journal_coeditor_code           BX2166
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1708
_journal_page_last               o1709
_journal_paper_doi               10.1107/S1600536808024690
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C20 H19 F2 N O'
_chemical_formula_moiety         'C20 H19 F2 N O'
_chemical_formula_sum            'C20 H19 F2 N O'
_chemical_formula_weight         327.36
_chemical_name_systematic
;
2,4-Bis(3-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-one
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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            4
_cell_length_a                   7.3844(2)
_cell_length_b                   21.5172(10)
_cell_length_c                   10.2608(4)
_cell_measurement_reflns_used    3860
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.20
_cell_volume                     1630.36(11)
_computing_cell_refinement       'APEX2 (Bruker--Nonius, 2004)'
_computing_data_collection       'APEX2 (Bruker--Nonius, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker--Nonius, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11640
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_correction_T_min  0.9667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.255
_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     118
_refine_ls_number_reflns         2069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0507
_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)+(0.0736P)²+0.4778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1544
_reflns_number_gt                1507
_reflns_number_total             2069
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2166.cif
_cod_data_source_block           I
_cod_database_code               2219278
_cod_database_fobs_code          2219278
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
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
C C1 0.9282(2) 0.30645(7) 0.60735(13) 0.0415(4) Uani d . 1
H H1 0.8910 0.3052 0.6990 0.050 Uiso calc R 1
C C2 0.75387(19) 0.30789(7) 0.52202(15) 0.0444(4) Uani d . 1
H H2 0.6813 0.3441 0.5468 0.053 Uiso calc R 1
C C3 0.7856(2) 0.30939(8) 0.37344(15) 0.0482(4) Uani d . 1
H H3A 0.6707 0.3166 0.3302 0.058 Uiso calc R 1
H H3B 0.8646 0.3441 0.3529 0.058 Uiso calc R 1
C C4 0.8693(3) 0.2500 0.3196(2) 0.0501(6) Uani d S 1
H H4A 0.8565 0.2500 0.2255 0.060 Uiso calc SR 1
H H4B 0.9978 0.2500 0.3394 0.060 Uiso calc SR 1
C C5 0.6479(3) 0.2500 0.5518(2) 0.0460(5) Uani d S 1
C C6 1.0432(2) 0.36362(7) 0.58774(14) 0.0436(4) Uani d . 1
C C7 1.1855(2) 0.36471(8) 0.49973(17) 0.0509(4) Uani d . 1
H H7 1.2153 0.3294 0.4522 0.061 Uiso calc R 1
C C8 1.2815(2) 0.41854(9) 0.4838(2) 0.0603(5) Uani d . 1
C C9 1.2457(3) 0.47171(9) 0.5505(2) 0.0723(6) Uani d . 1
H H9 1.3139 0.5075 0.5371 0.087 Uiso calc R 1
C C10 1.1056(3) 0.47077(9) 0.6385(2) 0.0767(7) Uani d . 1
H H10 1.0775 0.5065 0.6853 0.092 Uiso calc R 1
C C11 1.0059(3) 0.41717(8) 0.65820(19) 0.0599(5) Uani d . 1
H H11 0.9128 0.4170 0.7193 0.072 Uiso calc R 1
F F1 1.42123(18) 0.41845(6) 0.39681(15) 0.0962(5) Uani d . 1
N N1 1.0305(2) 0.2500 0.57975(17) 0.0395(4) Uani d S 1
O O1 0.4936(2) 0.2500 0.59191(18) 0.0638(5) Uani d S 1
H H1A 1.127(3) 0.2500 0.629(2) 0.047(6) Uiso d S 1
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
N1 C1 C6 . . 111.20(12)
N1 C1 C2 . . 109.63(12)
C6 C1 C2 . . 111.97(12)
N1 C1 H1 . . 108.0
C6 C1 H1 . . 108.0
C2 C1 H1 . . 108.0
C5 C2 C3 . . 107.30(14)
C5 C2 C1 . . 107.44(13)
C3 C2 C1 . . 115.49(12)
C5 C2 H2 . . 108.8
C3 C2 H2 . . 108.8
C1 C2 H2 . . 108.8
C4 C3 C2 . . 113.73(14)
C4 C3 H3A . . 108.8
C2 C3 H3A . . 108.8
C4 C3 H3B . . 108.8
C2 C3 H3B . . 108.8
H3A C3 H3B . . 107.7
C3 C4 C3 7_565 . 114.07(18)
C3 C4 H4A 7_565 . 108.7
C3 C4 H4A . . 108.7
C3 C4 H4B 7_565 . 108.7
C3 C4 H4B . . 108.7
H4A C4 H4B . . 107.6
O1 C5 C2 . . 123.98(8)
O1 C5 C2 . 7_565 123.98(8)
C2 C5 C2 . 7_565 112.01(17)
C7 C6 C11 . . 118.42(16)
C7 C6 C1 . . 121.85(13)
C11 C6 C1 . . 119.73(15)
C8 C7 C6 . . 119.02(16)
C8 C7 H7 . . 120.5
C6 C7 H7 . . 120.5
C9 C8 F1 . . 118.52(17)
C9 C8 C7 . . 123.5(2)
F1 C8 C7 . . 117.96(17)
C8 C9 C10 . . 117.71(19)
C8 C9 H9 . . 121.1
C10 C9 H9 . . 121.1
C9 C10 C11 . . 120.63(18)
C9 C10 H10 . . 119.7
C11 C10 H10 . . 119.7
C10 C11 C6 . . 120.68(19)
C10 C11 H11 . . 119.7
C6 C11 H11 . . 119.7
C1 N1 C1 7_565 . 112.78(16)
C1 N1 H1A 7_565 . 108.1(8)
C1 N1 H1A . . 108.1(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.4585(17)
C1 C6 . 1.508(2)
C1 C2 . 1.557(2)
C1 H1 . 0.9800
C2 C5 . 1.5025(19)
C2 C3 . 1.543(2)
C2 H2 . 0.9800
C3 C4 . 1.523(2)
C3 H3A . 0.9700
C3 H3B . 0.9700
C4 C3 7_565 1.523(2)
C4 H4A . 0.9700
C4 H4B . 0.9700
C5 O1 . 1.212(2)
C5 C2 7_565 1.5025(19)
C6 C7 . 1.386(2)
C6 C11 . 1.388(2)
C7 C8 . 1.368(2)
C7 H7 . 0.9300
C8 C9 . 1.359(3)
C8 F1 . 1.364(2)
C9 C10 . 1.373(3)
C9 H9 . 0.9300
C10 C11 . 1.383(3)
C10 H10 . 0.9300
C11 H11 . 0.9300
N1 C1 7_565 1.4585(17)
N1 H1A . 0.87(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C4 H4B N1 . 0.97 2.48 2.923(3) 108
C11 H11 Cg1 4_456 0.93 2.93 3.862(2) 175
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_4
_geom_torsion
N1 C1 C2 C5 . 57.58(16)
C6 C1 C2 C5 . -178.52(13)
N1 C1 C2 C3 . -62.09(17)
C6 C1 C2 C3 . 61.81(17)
C5 C2 C3 C4 . -52.65(18)
C1 C2 C3 C4 . 67.10(18)
C2 C3 C4 C3 7_565 44.0(2)
C3 C2 C5 O1 . -113.3(2)
C1 C2 C5 O1 . 122.0(2)
C3 C2 C5 C2 7_565 65.0(2)
C1 C2 C5 C2 7_565 -59.8(2)
N1 C1 C6 C7 . 28.45(19)
C2 C1 C6 C7 . -94.57(16)
N1 C1 C6 C11 . -152.20(15)
C2 C1 C6 C11 . 84.78(17)
C11 C6 C7 C8 . -1.2(2)
C1 C6 C7 C8 . 178.18(15)
C6 C7 C8 C9 . 0.4(3)
C6 C7 C8 F1 . 179.86(15)
F1 C8 C9 C10 . -179.43(17)
C7 C8 C9 C10 . 0.1(3)
C8 C9 C10 C11 . 0.4(3)
C9 C10 C11 C6 . -1.2(3)
C7 C6 C11 C10 . 1.6(3)
C1 C6 C11 C10 . -177.76(16)
C6 C1 N1 C1 7_565 175.53(10)
C2 C1 N1 C1 7_565 -60.11(18)
