#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/93/2229325.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_2229325
loop_
_publ_author_name
'Parthiban, P.'
'Ramkumar, V.'
'Jeong, Yeon Tae'
_publ_section_title
;
 2,4-Bis(4-butoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one
;
_journal_coeditor_code           BQ2279
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o635
_journal_paper_doi               10.1107/S1600536811005058
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C28 H37 N O3'
_chemical_formula_moiety         'C28 H37 N O3'
_chemical_formula_sum            'C28 H37 N O3'
_chemical_formula_weight         435.59
_chemical_name_systematic
;
2,4-Bis(4-butoxyphenyl)-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                   7.7780(5)
_cell_length_b                   31.457(2)
_cell_length_c                   9.9560(6)
_cell_measurement_reflns_used    4431
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.9
_cell_measurement_theta_min      3.3
_cell_volume                     2436.0(3)
_computing_cell_refinement       'APEX2 and 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 0.983
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10360
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0560
_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)+(0.0606P)²+1.2024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1634
_reflns_number_gt                1900
_reflns_number_total             2991
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2279.cif
_cod_data_source_block           I
_cod_database_code               2229325
_cod_database_fobs_code          2229325
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 1.1848(3) 0.71161(6) 0.10972(19) 0.0455(5) Uani d . 1 . .
H H1 1.2239 0.7136 0.2031 0.055 Uiso calc R 1 . .
C C2 1.3471(3) 0.71050(6) 0.0188(2) 0.0487(5) Uani d . 1 . .
H H2 1.4165 0.6857 0.0432 0.058 Uiso calc R 1 . .
C C3 1.4496(4) 0.7500 0.0466(3) 0.0494(7) Uani d S 1 . .
C C4 1.3130(3) 0.70937(6) -0.1338(2) 0.0523(5) Uani d . 1 . .
H H4A 1.4208 0.7044 -0.1801 0.063 Uiso calc R 1 . .
H H4B 1.2372 0.6857 -0.1536 0.063 Uiso calc R 1 . .
C C5 1.2325(4) 0.7500 -0.1884(3) 0.0547(7) Uani d S 1 . .
H H5A 1.1109 0.7500 -0.1667 0.066 Uiso calc SR 1 . .
H H5B 1.2429 0.7500 -0.2855 0.066 Uiso calc SR 1 . .
C C6 1.0781(3) 0.67181(6) 0.09708(18) 0.0440(4) Uani d . 1 . .
C C7 0.9491(3) 0.66660(6) 0.0020(2) 0.0542(5) Uani d . 1 . .
H H7 0.9213 0.6891 -0.0544 0.065 Uiso calc R 1 . .
C C8 0.8618(3) 0.62882(7) -0.0105(2) 0.0560(5) Uani d . 1 . .
H H8 0.7765 0.6260 -0.0753 0.067 Uiso calc R 1 . .
C C9 0.9001(3) 0.59496(6) 0.0730(2) 0.0495(5) Uani d . 1 . .
C C10 1.0237(3) 0.59983(6) 0.1706(2) 0.0530(5) Uani d . 1 . .
H H10 1.0487 0.5775 0.2288 0.064 Uiso calc R 1 . .
C C11 1.1108(3) 0.63806(6) 0.1821(2) 0.0500(5) Uani d . 1 . .
H H11 1.1936 0.6411 0.2489 0.060 Uiso calc R 1 . .
C C12 0.8378(3) 0.52285(6) 0.1337(2) 0.0601(6) Uani d . 1 . .
H H12A 0.8154 0.5296 0.2271 0.072 Uiso calc R 1 . .
H H12B 0.9567 0.5139 0.1253 0.072 Uiso calc R 1 . .
C C13 0.7190(3) 0.48792(7) 0.0868(3) 0.0663(6) Uani d . 1 . .
H H13A 0.6013 0.4978 0.0945 0.080 Uiso calc R 1 . .
H H13B 0.7413 0.4825 -0.0075 0.080 Uiso calc R 1 . .
C C14 0.7355(4) 0.44743(7) 0.1615(3) 0.0752(7) Uani d . 1 . .
H H14A 0.7082 0.4523 0.2553 0.090 Uiso calc R 1 . .
H H14B 0.8538 0.4377 0.1566 0.090 Uiso calc R 1 . .
C C15 0.6187(4) 0.41318(8) 0.1070(3) 0.0882(9) Uani d . 1 . .
H H15A 0.5020 0.4231 0.1080 0.132 Uiso calc R 1 . .
H H15B 0.6283 0.3882 0.1618 0.132 Uiso calc R 1 . .
H H15C 0.6517 0.4065 0.0165 0.132 Uiso calc R 1 . .
N N1 1.0856(3) 0.7500 0.0803(2) 0.0456(5) Uani d S 1 . .
O O1 1.5979(3) 0.7500 0.0826(2) 0.0692(6) Uani d S 1 . .
O O2 0.8061(2) 0.55880(5) 0.05158(16) 0.0662(5) Uani d . 1 . .
H H1N 0.991(4) 0.7500 0.127(3) 0.052(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 . . 112.25(17) ?
N1 C1 C2 . . 109.31(16) ?
C6 C1 C2 . . 112.33(15) ?
N1 C1 H1 . . 107.6 ?
C6 C1 H1 . . 107.6 ?
C2 C1 H1 . . 107.6 ?
C3 C2 C4 . . 106.96(18) ?
C3 C2 C1 . . 107.76(17) ?
C4 C2 C1 . . 115.76(17) ?
C3 C2 H2 . . 108.7 ?
C4 C2 H2 . . 108.7 ?
C1 C2 H2 . . 108.7 ?
O1 C3 C2 . . 124.15(12) ?
O1 C3 C2 . 7_575 124.15(12) ?
C2 C3 C2 . 7_575 111.7(2) ?
C5 C4 C2 . . 113.74(17) ?
C5 C4 H4A . . 108.8 ?
C2 C4 H4A . . 108.8 ?
C5 C4 H4B . . 108.8 ?
C2 C4 H4B . . 108.8 ?
H4A C4 H4B . . 107.7 ?
C4 C5 C4 . 7_575 114.1(2) ?
C4 C5 H5A . . 108.7 ?
C4 C5 H5A 7_575 . 108.7 ?
C4 C5 H5B . . 108.7 ?
C4 C5 H5B 7_575 . 108.7 ?
H5A C5 H5B . . 107.6 ?
C11 C6 C7 . . 117.37(18) ?
C11 C6 C1 . . 119.07(18) ?
C7 C6 C1 . . 123.54(17) ?
C8 C7 C6 . . 121.36(18) ?
C8 C7 H7 . . 119.3 ?
C6 C7 H7 . . 119.3 ?
C7 C8 C9 . . 120.3(2) ?
C7 C8 H8 . . 119.8 ?
C9 C8 H8 . . 119.8 ?
O2 C9 C10 . . 125.15(18) ?
O2 C9 C8 . . 115.55(18) ?
C10 C9 C8 . . 119.29(19) ?
C9 C10 C11 . . 119.77(18) ?
C9 C10 H10 . . 120.1 ?
C11 C10 H10 . . 120.1 ?
C6 C11 C10 . . 121.80(19) ?
C6 C11 H11 . . 119.1 ?
C10 C11 H11 . . 119.1 ?
O2 C12 C13 . . 107.21(19) ?
O2 C12 H12A . . 110.3 ?
C13 C12 H12A . . 110.3 ?
O2 C12 H12B . . 110.3 ?
C13 C12 H12B . . 110.3 ?
H12A C12 H12B . . 108.5 ?
C14 C13 C12 . . 114.7(2) ?
C14 C13 H13A . . 108.6 ?
C12 C13 H13A . . 108.6 ?
C14 C13 H13B . . 108.6 ?
C12 C13 H13B . . 108.6 ?
H13A C13 H13B . . 107.6 ?
C13 C14 C15 . . 112.4(2) ?
C13 C14 H14A . . 109.1 ?
C15 C14 H14A . . 109.1 ?
C13 C14 H14B . . 109.1 ?
C15 C14 H14B . . 109.1 ?
H14A C14 H14B . . 107.9 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C1 N1 C1 . 7_575 111.3(2) ?
C1 N1 H1N . . 109.8(9) ?
C1 N1 H1N 7_575 . 109.8(9) ?
C9 O2 C12 . . 118.72(17) ?
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 . 1.463(2) ?
C1 C6 . 1.507(3) ?
C1 C2 . 1.554(3) ?
C1 H1 . 0.9800 ?
C2 C3 . 1.502(2) ?
C2 C4 . 1.543(3) ?
C2 H2 . 0.9800 ?
C3 O1 . 1.208(3) ?
C3 C2 7_575 1.502(2) ?
C4 C5 . 1.523(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C4 7_575 1.523(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C11 . 1.382(3) ?
C6 C7 . 1.390(3) ?
C7 C8 . 1.374(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.384(3) ?
C8 H8 . 0.9300 ?
C9 O2 . 1.369(2) ?
C9 C10 . 1.376(3) ?
C10 C11 . 1.385(3) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 O2 . 1.417(2) ?
C12 C13 . 1.510(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.481(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.510(4) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
N1 C1 7_575 1.463(2) ?
N1 H1N . 0.87(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 C3 . . . . 58.7(2) ?
C6 C1 C2 C3 . . . . -176.04(17) ?
N1 C1 C2 C4 . . . . -61.0(2) ?
C6 C1 C2 C4 . . . . 64.3(2) ?
C4 C2 C3 O1 . . . . -111.7(3) ?
C1 C2 C3 O1 . . . . 123.2(3) ?
C4 C2 C3 C2 . . . 7_575 66.0(3) ?
C1 C2 C3 C2 . . . 7_575 -59.1(3) ?
C3 C2 C4 C5 . . . . -52.9(2) ?
C1 C2 C4 C5 . . . . 67.2(2) ?
C2 C4 C5 C4 . . . 7_575 43.6(3) ?
N1 C1 C6 C11 . . . . -145.94(19) ?
C2 C1 C6 C11 . . . . 90.4(2) ?
N1 C1 C6 C7 . . . . 35.4(3) ?
C2 C1 C6 C7 . . . . -88.3(2) ?
C11 C6 C7 C8 . . . . -2.4(3) ?
C1 C6 C7 C8 . . . . 176.3(2) ?
C6 C7 C8 C9 . . . . 0.5(3) ?
C7 C8 C9 O2 . . . . -179.7(2) ?
C7 C8 C9 C10 . . . . 1.5(3) ?
O2 C9 C10 C11 . . . . 179.82(19) ?
C8 C9 C10 C11 . . . . -1.6(3) ?
C7 C6 C11 C10 . . . . 2.4(3) ?
C1 C6 C11 C10 . . . . -176.39(18) ?
C9 C10 C11 C6 . . . . -0.4(3) ?
O2 C12 C13 C14 . . . . 179.6(2) ?
C12 C13 C14 C15 . . . . -177.8(2) ?
C6 C1 N1 C1 . . . 7_575 172.73(12) ?
C2 C1 N1 C1 . . . 7_575 -61.9(2) ?
C10 C9 O2 C12 . . . . -1.0(3) ?
C8 C9 O2 C12 . . . . -179.72(19) ?
C13 C12 O2 C9 . . . . -179.18(19) ?
