#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/38/2013877.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_2013877
loop_
_publ_author_name
'Zheng, Guangrong'
'Parkin, Sean'
'Dwoskin, Linda P.'
'Crooks, Peter A.'
_publ_section_title
;
 Two isomers of 2,4-dibenzyl-8-azabicyclo[3.2.1]octan-3-ol
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o9
_journal_page_last               o11
_journal_paper_doi               10.1107/S0108270103026520
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C22 H27 N O'
_chemical_formula_moiety         'C22 H27 N O'
_chemical_formula_sum            'C22 H27 N O'
_chemical_formula_weight         321.45
_chemical_name_common            '2α, 4α-dibenzyl-3α-tropanol'
_chemical_name_systematic
;
2α,4α-dibenzyl-8-methyl-8-azabicyclo[3.2.1]octane-3α-ol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                   10.4244(4)
_cell_length_b                   11.4988(5)
_cell_length_c                   15.1602(5)
_cell_measurement_reflns_used    11302
_cell_measurement_temperature    206.0(10)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1817.22(12)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO--SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 1994)'
_computing_publication_material
;
SHELX97-2 (Sheldrick, 1997) and local procedures
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      206.0(10)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_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  0.0657
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14506
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.174
_refine_ls_abs_structure_details
;
  Flack H D (1983), Acta Cryst. A39, 876-881
  The absolute structure of the crystal cannot be determined from the x-ray
  data because it is an all light atom structure determined with Mo Kα data.
  The quoted value of the Flack parameter was obtained in the conventional
  way, as a variable in a full-matrix least-squares refinement against data
  with unmerged Friedel opposites.  In the final refinement cycles, performed
  against Friedel-merged data, the Flack parameter was not refined because it
  had previously refined to a value with no physical interpretation.
;
_refine_ls_abs_structure_Flack   0.7(19)
_refine_ls_extinction_coef       0.0126(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.441
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.441
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0496P)²+0.0877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                1902
_reflns_number_total             2371
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq1138.cif
_cod_data_source_block           I
_cod_database_code               2013877
_cod_database_fobs_code          2013877
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_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
_atom_site_type_symbol
N 1.08785(15) 0.09661(14) -0.04257(10) 0.0277(4) Uani d . 1 . . N
O 0.77051(12) 0.26049(13) -0.03745(9) 0.0319(4) Uani d . 1 . . O
H0 0.7232 0.3055 -0.0096 0.048 Uiso calc R 1 . . H
C1 1.01261(19) 0.14121(17) -0.11883(13) 0.0283(5) Uani d . 1 . . C
H1 1.0622 0.1331 -0.1742 0.034 Uiso calc R 1 . . H
C2 0.98372(19) 0.27026(17) -0.09993(12) 0.0251(4) Uani d . 1 . . C
H2 1.0673 0.3075 -0.0870 0.030 Uiso calc R 1 . . H
C3 0.90163(17) 0.28534(18) -0.01704(12) 0.0256(4) Uani d . 1 . . C
H3 0.9075 0.3675 0.0020 0.031 Uiso calc R 1 . . H
C4 0.95351(18) 0.20822(17) 0.05783(12) 0.0258(5) Uani d . 1 . . C
H4 1.0357 0.2434 0.0768 0.031 Uiso calc R 1 . . H
C5 0.98545(18) 0.08504(17) 0.02506(13) 0.0285(5) Uani d . 1 . . C
H5 1.0152 0.0358 0.0746 0.034 Uiso calc R 1 . . H
C6 0.8735(2) 0.02548(18) -0.02408(13) 0.0345(5) Uani d . 1 . . C
H6A 0.7906 0.0519 -0.0012 0.041 Uiso calc R 1 . . H
H6B 0.8786 -0.0593 -0.0184 0.041 Uiso calc R 1 . . H
C7 0.8920(2) 0.06369(19) -0.12132(13) 0.0342(5) Uani d . 1 . . C
H7A 0.9052 -0.0038 -0.1597 0.041 Uiso calc R 1 . . H
H7B 0.8174 0.1075 -0.1424 0.041 Uiso calc R 1 . . H
C8 1.1487(2) -0.01515(19) -0.06362(14) 0.0398(6) Uani d . 1 . . C
H8A 1.1966 -0.0425 -0.0128 0.060 Uiso calc R 1 . . H
H8B 1.2066 -0.0052 -0.1132 0.060 Uiso calc R 1 . . H
H8C 1.0832 -0.0716 -0.0788 0.060 Uiso calc R 1 . . H
C9 0.9287(2) 0.33359(17) -0.18033(14) 0.0322(5) Uani d . 1 . . C
H9A 0.9877 0.3239 -0.2301 0.039 Uiso calc R 1 . . H
H9B 0.8469 0.2974 -0.1965 0.039 Uiso calc R 1 . . H
C10 0.9072(2) 0.46137(18) -0.16500(12) 0.0322(5) Uani d . 1 . . C
C11 0.7854(2) 0.5101(2) -0.17276(14) 0.0432(6) Uani d . 1 . . C
H11 0.7154 0.4632 -0.1890 0.052 Uiso calc R 1 . . H
C12 0.7670(3) 0.6283(2) -0.15647(16) 0.0562(8) Uani d . 1 . . C
H12 0.6843 0.6603 -0.1613 0.067 Uiso calc R 1 . . H
C13 0.8679(3) 0.6983(2) -0.13349(16) 0.0608(9) Uani d . 1 . . C
H13 0.8546 0.7779 -0.1230 0.073 Uiso calc R 1 . . H
C14 0.9881(3) 0.6518(2) -0.12591(15) 0.0518(7) Uani d . 1 . . C
H14 1.0575 0.6996 -0.1102 0.062 Uiso calc R 1 . . H
C15 1.0077(3) 0.53445(19) -0.14136(14) 0.0398(6) Uani d . 1 . . C
H15 1.0908 0.5035 -0.1357 0.048 Uiso calc R 1 . . H
C16 0.86604(19) 0.2089(2) 0.13859(12) 0.0318(5) Uani d . 1 . . C
H16A 0.8296 0.2869 0.1453 0.038 Uiso calc R 1 . . H
H16B 0.7948 0.1550 0.1281 0.038 Uiso calc R 1 . . H
C17 0.93121(19) 0.17546(18) 0.22361(13) 0.0308(5) Uani d . 1 . . C
C18 1.0323(2) 0.2401(2) 0.25647(16) 0.0487(6) Uani d . 1 . . C
H18 1.0651 0.3026 0.2235 0.058 Uiso calc R 1 . . H
C19 1.0862(3) 0.2129(3) 0.33874(17) 0.0638(8) Uani d . 1 . . C
H19 1.1549 0.2571 0.3609 0.077 Uiso calc R 1 . . H
C20 1.0379(3) 0.1209(3) 0.38687(16) 0.0634(9) Uani d . 1 . . C
H20 1.0731 0.1030 0.4423 0.076 Uiso calc R 1 . . H
C21 0.9400(3) 0.0562(3) 0.35463(17) 0.0602(8) Uani d . 1 . . C
H21 0.9080 -0.0069 0.3873 0.072 Uiso calc R 1 . . H
C22 0.8875(2) 0.0830(2) 0.27393(14) 0.0443(6) Uani d . 1 . . C
H22 0.8198 0.0372 0.2522 0.053 Uiso calc R 1 . . H
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
_geom_angle_publ_flag
C8 N C5 112.46(15) ?
C8 N C1 111.14(15) ?
C5 N C1 100.85(14) ?
C3 O H0 109.5 ?
N C1 C2 106.88(15) y
N C1 C7 104.45(15) ?
C2 C1 C7 113.70(17) ?
N C1 H1 110.5 ?
C2 C1 H1 110.5 ?
C7 C1 H1 110.5 ?
C3 C2 C9 112.98(15) y
C3 C2 C1 111.78(16) ?
C9 C2 C1 112.53(16) ?
C3 C2 H2 106.3 ?
C9 C2 H2 106.3 ?
C1 C2 H2 106.3 ?
O C3 C2 109.51(15) y
O C3 C4 112.36(16) y
C2 C3 C4 110.12(15) ?
O C3 H3 108.2 ?
C2 C3 H3 108.2 ?
C4 C3 H3 108.2 ?
C16 C4 C5 113.14(16) ?
C16 C4 C3 112.27(15) y
C5 C4 C3 111.64(16) ?
C16 C4 H4 106.4 ?
C5 C4 H4 106.4 ?
C3 C4 H4 106.4 ?
N C5 C4 107.22(15) y
N C5 C6 104.45(15) ?
C4 C5 C6 113.63(17) ?
N C5 H5 110.4 ?
C4 C5 H5 110.4 ?
C6 C5 H5 110.4 ?
C5 C6 C7 103.85(16) ?
C5 C6 H6A 111.0 ?
C7 C6 H6A 111.0 ?
C5 C6 H6B 111.0 ?
C7 C6 H6B 111.0 ?
H6A C6 H6B 109.0 ?
C1 C7 C6 103.99(16) ?
C1 C7 H7A 111.0 ?
C6 C7 H7A 111.0 ?
C1 C7 H7B 111.0 ?
C6 C7 H7B 111.0 ?
H7A C7 H7B 109.0 ?
N C8 H8A 109.5 ?
N C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
N C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C10 C9 C2 113.41(17) ?
C10 C9 H9A 108.9 ?
C2 C9 H9A 108.9 ?
C10 C9 H9B 108.9 ?
C2 C9 H9B 108.9 ?
H9A C9 H9B 107.7 ?
C15 C10 C11 117.7(2) ?
C15 C10 C9 121.2(2) ?
C11 C10 C9 121.0(2) ?
C10 C11 C12 120.2(3) ?
C10 C11 H11 119.9 ?
C12 C11 H11 119.9 ?
C13 C12 C11 120.8(3) ?
C13 C12 H12 119.6 ?
C11 C12 H12 119.6 ?
C14 C13 C12 119.7(2) ?
C14 C13 H13 120.1 ?
C12 C13 H13 120.1 ?
C13 C14 C15 120.1(3) ?
C13 C14 H14 119.9 ?
C15 C14 H14 119.9 ?
C14 C15 C10 121.4(3) ?
C14 C15 H15 119.3 ?
C10 C15 H15 119.3 ?
C17 C16 C4 114.56(15) ?
C17 C16 H16A 108.6 ?
C4 C16 H16A 108.6 ?
C17 C16 H16B 108.6 ?
C4 C16 H16B 108.6 ?
H16A C16 H16B 107.6 ?
C18 C17 C22 117.7(2) ?
C18 C17 C16 121.0(2) ?
C22 C17 C16 121.20(19) ?
C17 C18 C19 120.4(3) ?
C17 C18 H18 119.8 ?
C19 C18 H18 119.8 ?
C20 C19 C18 119.6(3) ?
C20 C19 H19 120.2 ?
C18 C19 H19 120.2 ?
C21 C20 C19 120.3(3) ?
C21 C20 H20 119.8 ?
C19 C20 H20 119.8 ?
C20 C21 C22 119.9(3) ?
C20 C21 H21 120.0 ?
C22 C21 H21 120.0 ?
C21 C22 C17 122.0(2) ?
C21 C22 H22 119.0 ?
C17 C22 H22 119.0 ?
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
N C8 . 1.468(3) ?
N C5 . 1.486(2) y
N C1 . 1.488(2) y
O C3 . 1.430(2) ?
O H0 . 0.8300 ?
C1 C2 . 1.541(3) ?
C1 C7 . 1.542(3) ?
C1 H1 . 0.9900 ?
C2 C3 . 1.530(3) y
C2 C9 . 1.531(3) y
C2 H2 . 0.9900 ?
C3 C4 . 1.539(3) y
C3 H3 . 0.9900 ?
C4 C16 . 1.527(3) y
C4 C5 . 1.537(3) ?
C4 H4 . 0.9900 ?
C5 C6 . 1.544(3) ?
C5 H5 . 0.9900 ?
C6 C7 . 1.550(3) ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C8 H8C . 0.9700 ?
C9 C10 . 1.504(3) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C10 C15 . 1.390(3) ?
C10 C11 . 1.393(3) ?
C11 C12 . 1.394(4) ?
C11 H11 . 0.9400 ?
C12 C13 . 1.370(4) ?
C12 H12 . 0.9400 ?
C13 C14 . 1.366(4) ?
C13 H13 . 0.9400 ?
C14 C15 . 1.385(3) ?
C14 H14 . 0.9400 ?
C15 H15 . 0.9400 ?
C16 C17 . 1.507(3) ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C17 C18 . 1.382(3) ?
C17 C22 . 1.386(3) ?
C18 C19 . 1.403(3) ?
C18 H18 . 0.9400 ?
C19 C20 . 1.381(4) ?
C19 H19 . 0.9400 ?
C20 C21 . 1.354(4) ?
C20 H20 . 0.9400 ?
C21 C22 . 1.375(3) ?
C21 H21 . 0.9400 ?
C22 H22 . 0.9400 ?
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
_geom_torsion_publ_flag
C8 N C1 C2 -165.20(16) ?
C5 N C1 C2 75.39(18) ?
C8 N C1 C7 74.00(19) ?
C5 N C1 C7 -45.41(18) ?
N C1 C2 C3 -62.4(2) ?
C7 C1 C2 C3 52.3(2) ?
N C1 C2 C9 169.24(16) ?
C7 C1 C2 C9 -76.0(2) ?
C9 C2 C3 O 49.3(2) ?
C1 C2 C3 O -78.81(19) ?
C9 C2 C3 C4 173.36(16) ?
C1 C2 C3 C4 45.2(2) ?
O C3 C4 C16 -50.8(2) ?
C2 C3 C4 C16 -173.21(16) ?
O C3 C4 C5 77.42(19) ?
C2 C3 C4 C5 -45.0(2) ?
C8 N C5 C4 166.13(16) ?
C1 N C5 C4 -75.41(17) ?
C8 N C5 C6 -73.0(2) ?
C1 N C5 C6 45.47(18) ?
C16 C4 C5 N -170.24(15) ?
C3 C4 C5 N 62.0(2) ?
C16 C4 C5 C6 74.9(2) ?
C3 C4 C5 C6 -52.9(2) ?
N C5 C6 C7 -28.0(2) ?
C4 C5 C6 C7 88.53(19) ?
N C1 C7 C6 27.8(2) ?
C2 C1 C7 C6 -88.4(2) ?
C5 C6 C7 C1 0.1(2) ?
C3 C2 C9 C10 55.7(2) y
C1 C2 C9 C10 -176.53(18) y
C2 C9 C10 C15 58.9(3) y
C2 C9 C10 C11 -120.2(2) ?
C15 C10 C11 C12 -0.4(3) ?
C9 C10 C11 C12 178.65(19) ?
C10 C11 C12 C13 0.6(3) ?
C11 C12 C13 C14 -0.4(4) ?
C12 C13 C14 C15 0.0(4) ?
C13 C14 C15 C10 0.2(3) ?
C11 C10 C15 C14 0.0(3) ?
C9 C10 C15 C14 -179.0(2) ?
C5 C4 C16 C17 74.8(2) ?
C3 C4 C16 C17 -157.74(18) y
C4 C16 C17 C18 61.0(3) y
C4 C16 C17 C22 -122.6(2) ?
C22 C17 C18 C19 -1.0(3) ?
C16 C17 C18 C19 175.5(2) ?
C17 C18 C19 C20 0.1(4) ?
C18 C19 C20 C21 0.8(4) ?
C19 C20 C21 C22 -0.7(4) ?
C20 C21 C22 C17 -0.3(4) ?
C18 C17 C22 C21 1.1(3) ?
C16 C17 C22 C21 -175.4(2) ?
