#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/96/2229661.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_2229661
loop_
_publ_author_name
'Parthiban, P.'
'Ramkumar, V.'
'Jeong, Yeon Tae'
_publ_section_title
;
 2,4-Bis(4-propoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one
;
_journal_coeditor_code           HB5803
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o790
_journal_paper_doi               10.1107/S1600536811007483
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C26 H33 N O3'
_chemical_formula_moiety         'C26 H33 N O3'
_chemical_formula_sum            'C26 H33 N O3'
_chemical_formula_weight         407.53
_chemical_name_systematic
;
2,4-Bis(4-propoxyphenyl)-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                   7.3846(4)
_cell_length_b                   29.3963(19)
_cell_length_c                   10.2739(7)
_cell_measurement_reflns_used    1042
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.82
_cell_measurement_theta_min      2.29
_cell_volume                     2230.3(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 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 0.905
_diffrn_measured_fraction_theta_max 0.810
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7260
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.22
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0440
_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)+(0.0404P)²+0.4368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                1121
_reflns_number_total             1860
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5803.cif
_cod_data_source_block           I
_cod_database_code               2229661
_cod_database_fobs_code          2229661
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6512(3) 0.29134(6) 0.6070(2) 0.0384(5) Uani d . 1 . .
H H1 0.6934 0.2893 0.6972 0.046 Uiso calc R 1 . .
C C2 0.8207(3) 0.29225(7) 0.5180(2) 0.0426(6) Uani d . 1 . .
H H2 0.8944 0.3188 0.5408 0.051 Uiso calc R 1 . .
C C3 0.7815(3) 0.29351(7) 0.3708(2) 0.0474(6) Uani d . 1 . .
H H3A 0.7004 0.3187 0.3529 0.057 Uiso calc R 1 . .
H H3B 0.8940 0.2993 0.3249 0.057 Uiso calc R 1 . .
C C4 0.6973(4) 0.2500 0.3174(3) 0.0482(8) Uani d S 1 . .
H H4A 0.7093 0.2500 0.2234 0.058 Uiso calc SR 1 . .
H H4B 0.5691 0.2500 0.3377 0.058 Uiso calc SR 1 . .
C C5 0.9286(4) 0.2500 0.5451(3) 0.0437(8) Uani d S 1 . .
C C6 0.5396(3) 0.33407(7) 0.5949(2) 0.0364(5) Uani d . 1 . .
C C7 0.3900(3) 0.33809(7) 0.5140(2) 0.0418(6) Uani d . 1 . .
H H7 0.3506 0.3130 0.4666 0.050 Uiso calc R 1 . .
C C8 0.2990(3) 0.37892(7) 0.5032(2) 0.0426(6) Uani d . 1 . .
H H8 0.1988 0.3811 0.4488 0.051 Uiso calc R 1 . .
C C9 0.3553(3) 0.41666(7) 0.5724(2) 0.0389(6) Uani d . 1 . .
C C10 0.5009(3) 0.41290(7) 0.6550(2) 0.0480(6) Uani d . 1 . .
H H10 0.5384 0.4378 0.7040 0.058 Uiso calc R 1 . .
C C11 0.5911(3) 0.37188(7) 0.6647(2) 0.0462(6) Uani d . 1 . .
H H11 0.6901 0.3697 0.7204 0.055 Uiso calc R 1 . .
C C12 0.3046(3) 0.49521(7) 0.6265(2) 0.0484(6) Uani d . 1 . .
H H12A 0.4284 0.5039 0.6070 0.058 Uiso calc R 1 . .
H H12B 0.2959 0.4889 0.7190 0.058 Uiso calc R 1 . .
C C13 0.1778(3) 0.53290(7) 0.5904(2) 0.0578(7) Uani d . 1 . .
H H13A 0.0545 0.5237 0.6096 0.069 Uiso calc R 1 . .
H H13B 0.1863 0.5386 0.4976 0.069 Uiso calc R 1 . .
C C14 0.2201(4) 0.57630(8) 0.6634(3) 0.0768(9) Uani d . 1 . .
H H14A 0.2116 0.5708 0.7554 0.115 Uiso calc R 1 . .
H H14B 0.1350 0.5995 0.6390 0.115 Uiso calc R 1 . .
H H14C 0.3405 0.5861 0.6423 0.115 Uiso calc R 1 . .
N N1 0.5477(4) 0.2500 0.5790(3) 0.0405(7) Uani d S 1 . .
O O1 1.0831(3) 0.2500 0.5851(2) 0.0633(7) Uani d S 1 . .
O O2 0.25630(19) 0.45579(5) 0.55359(16) 0.0531(5) Uani d . 1 . .
H H1N 0.458(4) 0.2500 0.623(3) 0.029(9) 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'
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
_geom_angle_publ_flag
N1 C1 C6 . . 112.97(17) ?
N1 C1 C2 . . 108.69(19) ?
C6 C1 C2 . . 112.25(17) ?
N1 C1 H1 . . 107.6 ?
C6 C1 H1 . . 107.6 ?
C2 C1 H1 . . 107.6 ?
C5 C2 C3 . . 107.6(2) ?
C5 C2 C1 . . 107.73(19) ?
C3 C2 C1 . . 115.30(17) ?
C5 C2 H2 . . 108.7 ?
C3 C2 H2 . . 108.7 ?
C1 C2 H2 . . 108.7 ?
C4 C3 C2 . . 114.2(2) ?
C4 C3 H3A . . 108.7 ?
C2 C3 H3A . . 108.7 ?
C4 C3 H3B . . 108.7 ?
C2 C3 H3B . . 108.7 ?
H3A C3 H3B . . 107.6 ?
C3 C4 C3 . 7_565 114.1(3) ?
C3 C4 H4A . . 108.7 ?
C3 C4 H4A 7_565 . 108.7 ?
C3 C4 H4B . . 108.7 ?
C3 C4 H4B 7_565 . 108.7 ?
H4A C4 H4B . . 107.6 ?
O1 C5 C2 . 7_565 124.19(13) ?
O1 C5 C2 . . 124.19(13) ?
C2 C5 C2 7_565 . 111.6(3) ?
C11 C6 C7 . . 117.62(19) ?
C11 C6 C1 . . 118.61(18) ?
C7 C6 C1 . . 123.75(19) ?
C8 C7 C6 . . 120.7(2) ?
C8 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
C7 C8 C9 . . 120.7(2) ?
C7 C8 H8 . . 119.6 ?
C9 C8 H8 . . 119.6 ?
C10 C9 O2 . . 124.69(19) ?
C10 C9 C8 . . 119.24(19) ?
O2 C9 C8 . . 116.06(19) ?
C9 C10 C11 . . 119.5(2) ?
C9 C10 H10 . . 120.3 ?
C11 C10 H10 . . 120.3 ?
C6 C11 C10 . . 122.3(2) ?
C6 C11 H11 . . 118.9 ?
C10 C11 H11 . . 118.9 ?
O2 C12 C13 . . 108.35(18) ?
O2 C12 H12A . . 110.0 ?
C13 C12 H12A . . 110.0 ?
O2 C12 H12B . . 110.0 ?
C13 C12 H12B . . 110.0 ?
H12A C12 H12B . . 108.4 ?
C12 C13 C14 . . 111.9(2) ?
C12 C13 H13A . . 109.2 ?
C14 C13 H13A . . 109.2 ?
C12 C13 H13B . . 109.2 ?
C14 C13 H13B . . 109.2 ?
H13A C13 H13B . . 107.9 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C1 N1 C1 . 7_565 112.2(2) ?
C1 N1 H1N . . 108.6(10) ?
C1 N1 H1N 7_565 . 108.6(10) ?
C9 O2 C12 . . 118.21(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.464(2) ?
C1 C6 . 1.507(3) ?
C1 C2 . 1.551(3) ?
C1 H1 . 0.9800 ?
C2 C5 . 1.502(3) ?
C2 C3 . 1.540(3) ?
C2 H2 . 0.9800 ?
C3 C4 . 1.524(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C3 7_565 1.524(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 O1 . 1.213(3) ?
C5 C2 7_565 1.502(3) ?
C6 C11 . 1.377(3) ?
C6 C7 . 1.387(3) ?
C7 C8 . 1.380(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.381(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.375(3) ?
C9 O2 . 1.376(2) ?
C10 C11 . 1.381(3) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 O2 . 1.425(2) ?
C12 C13 . 1.497(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.512(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
N1 C1 7_565 1.464(2) ?
N1 H1N . 0.80(3) ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C5 . . . . -58.5(2) ?
C6 C1 C2 C5 . . . . 175.77(19) ?
N1 C1 C2 C3 . . . . 61.6(2) ?
C6 C1 C2 C3 . . . . -64.1(2) ?
C5 C2 C3 C4 . . . . 52.0(3) ?
C1 C2 C3 C4 . . . . -68.2(3) ?
C2 C3 C4 C3 . . . 7_565 -42.1(3) ?
C3 C2 C5 O1 . . . . 115.5(3) ?
C1 C2 C5 O1 . . . . -119.6(3) ?
C3 C2 C5 C2 . . . 7_565 -65.1(3) ?
C1 C2 C5 C2 . . . 7_565 59.8(3) ?
N1 C1 C6 C11 . . . . 154.5(2) ?
C2 C1 C6 C11 . . . . -82.1(2) ?
N1 C1 C6 C7 . . . . -27.5(3) ?
C2 C1 C6 C7 . . . . 95.8(2) ?
C11 C6 C7 C8 . . . . 1.0(3) ?
C1 C6 C7 C8 . . . . -177.0(2) ?
C6 C7 C8 C9 . . . . 0.2(3) ?
C7 C8 C9 C10 . . . . -1.6(3) ?
C7 C8 C9 O2 . . . . 179.35(19) ?
O2 C9 C10 C11 . . . . -179.3(2) ?
C8 C9 C10 C11 . . . . 1.7(3) ?
C7 C6 C11 C10 . . . . -0.9(3) ?
C1 C6 C11 C10 . . . . 177.2(2) ?
C9 C10 C11 C6 . . . . -0.5(3) ?
O2 C12 C13 C14 . . . . -179.8(2) ?
C6 C1 N1 C1 . . . 7_565 -172.82(15) ?
C2 C1 N1 C1 . . . 7_565 61.9(3) ?
C10 C9 O2 C12 . . . . -1.4(3) ?
C8 C9 O2 C12 . . . . 177.64(18) ?
C13 C12 O2 C9 . . . . -179.52(18) ?
