#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:13:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178426 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/47/4024770.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024770
loop_
_publ_author_name
'Guangrong Zheng'
'Linda P. Dwoskin'
'Agripina G. Deaciuc'
'Peter A. Crooks'
_publ_section_title
;
Stereocontrolled Synthesis and Pharmacological Evaluation
of cis-2,6-Diphenethyl-1-azabicyclo[2.2.2]octanes as Lobelane Analogues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6072
_journal_page_last               6076
_journal_paper_doi               10.1021/jo901082r
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C16 H12 Cl3 N O3'
_chemical_formula_weight         372.62
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                63.082(1)
_cell_angle_beta                 74.631(1)
_cell_angle_gamma                82.194(1)
_cell_formula_units_Z            2
_cell_length_a                   9.6240(2)
_cell_length_b                   9.9066(2)
_cell_length_c                   10.2640(2)
_cell_measurement_reflns_used    3710
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     841.25(3)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7357
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  0.8733
_exptl_absorpt_correction_T_min  0.8507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.487
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.487
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0411
_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)+(0.0451P)²+0.4771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1068
_reflns_number_gt                3087
_reflns_number_total             3861
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo901082r_si_001.cif
_cod_data_source_block           k03192
_cod_database_code               4024770
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.34567(5) 0.56477(6) 0.32319(6) 0.03946(15) Uani 1 1 d . . .
Cl2 Cl -0.49111(7) 0.46041(8) 0.17541(8) 0.05438(19) Uani 1 1 d . . .
Cl3 Cl -0.18705(8) 0.52876(8) 0.06048(7) 0.0652(2) Uani 1 1 d . . .
O1 O 0.39010(15) 0.15727(17) 0.58390(17) 0.0389(3) Uani 1 1 d . . .
N1 N 0.05457(16) 0.19728(17) 0.39301(17) 0.0247(3) Uani 1 1 d . . .
C1 C 0.05106(19) 0.2905(2) 0.4731(2) 0.0248(4) Uani 1 1 d . . .
H1 H -0.0512 0.3010 0.5237 0.030 Uiso 1 1 calc R . .
O2 O -0.17040(13) 0.27826(15) 0.37337(15) 0.0285(3) Uani 1 1 d . . .
C2 C 0.13784(19) 0.2101(2) 0.5930(2) 0.0265(4) Uani 1 1 d . . .
H2A H 0.1461 0.2785 0.6370 0.032 Uiso 1 1 calc R . .
H2B H 0.0854 0.1193 0.6743 0.032 Uiso 1 1 calc R . .
O3 O -0.05044(14) 0.14425(15) 0.24590(15) 0.0321(3) Uani 1 1 d . . .
C3 C 0.2873(2) 0.1625(2) 0.5322(2) 0.0292(4) Uani 1 1 d . . .
C4 C 0.2966(2) 0.1144(2) 0.4152(2) 0.0313(4) Uani 1 1 d . . .
H4 H 0.3849 0.0728 0.3796 0.038 Uiso 1 1 calc R . .
C5 C 0.1841(2) 0.1272(2) 0.3568(2) 0.0288(4) Uani 1 1 d . . .
H5 H 0.1931 0.0863 0.2871 0.035 Uiso 1 1 calc R . .
C6 C -0.05592(19) 0.2023(2) 0.3276(2) 0.0254(4) Uani 1 1 d . . .
C7 C -0.2964(2) 0.2895(2) 0.3198(2) 0.0313(4) Uani 1 1 d . . .
H7A H -0.3796 0.2463 0.4058 0.038 Uiso 1 1 calc R . .
H7B H -0.2810 0.2316 0.2597 0.038 Uiso 1 1 calc R . .
C8 C -0.3269(2) 0.4547(2) 0.2238(2) 0.0327(4) Uani 1 1 d . . .
C9 C 0.10602(19) 0.4425(2) 0.3663(2) 0.0270(4) Uani 1 1 d . . .
C10 C 0.15078(19) 0.5672(2) 0.2851(2) 0.0273(4) Uani 1 1 d . . .
C11 C 0.20396(19) 0.7187(2) 0.1960(2) 0.0263(4) Uani 1 1 d . . .
C12 C 0.1545(2) 0.8166(2) 0.0682(2) 0.0371(5) Uani 1 1 d . . .
H12 H 0.0882 0.7830 0.0355 0.045 Uiso 1 1 calc R . .
C13 C 0.2037(3) 0.9643(3) -0.0110(3) 0.0492(6) Uani 1 1 d . . .
H13 H 0.1698 1.0320 -0.0977 0.059 Uiso 1 1 calc R . .
C14 C 0.3008(3) 1.0140(2) 0.0345(3) 0.0461(6) Uani 1 1 d . . .
H14 H 0.3327 1.1155 -0.0202 0.055 Uiso 1 1 calc R . .
C15 C 0.3517(2) 0.9163(2) 0.1596(2) 0.0373(5) Uani 1 1 d . . .
H15 H 0.4200 0.9501 0.1899 0.045 Uiso 1 1 calc R . .
C16 C 0.3033(2) 0.7695(2) 0.2408(2) 0.0290(4) Uani 1 1 d . . .
H16 H 0.3377 0.7027 0.3275 0.035 Uiso 1 1 calc R . .
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C5 118.46(15) . . ?
C6 N1 C1 122.14(14) . . ?
C5 N1 C1 118.11(14) . . ?
C9 C1 N1 110.39(14) . . ?
C9 C1 C2 111.68(15) . . ?
N1 C1 C2 109.29(14) . . ?
C9 C1 H1 108.5 . . ?
N1 C1 H1 108.5 . . ?
C2 C1 H1 108.5 . . ?
C6 O2 C7 116.69(14) . . ?
C3 C2 C1 112.78(15) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
O1 C3 C4 123.12(17) . . ?
O1 C3 C2 122.04(17) . . ?
C4 C3 C2 114.72(16) . . ?
C5 C4 C3 121.74(17) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 N1 123.17(17) . . ?
C4 C5 H5 118.4 . . ?
N1 C5 H5 118.4 . . ?
O3 C6 O2 125.87(17) . . ?
O3 C6 N1 124.60(17) . . ?
O2 C6 N1 109.51(14) . . ?
O2 C7 C8 109.07(15) . . ?
O2 C7 H7A 109.9 . . ?
C8 C7 H7A 109.9 . . ?
O2 C7 H7B 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C7 C8 Cl2 106.31(14) . . ?
C7 C8 Cl1 111.63(13) . . ?
Cl2 C8 Cl1 109.04(10) . . ?
C7 C8 Cl3 110.49(13) . . ?
Cl2 C8 Cl3 110.32(11) . . ?
Cl1 C8 Cl3 109.01(11) . . ?
C10 C9 C1 176.98(19) . . ?
C9 C10 C11 176.24(19) . . ?
C12 C11 C16 119.67(18) . . ?
C12 C11 C10 120.84(18) . . ?
C16 C11 C10 119.46(16) . . ?
C13 C12 C11 119.0(2) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.28(18) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.766(2) . ?
Cl2 C8 1.765(2) . ?
Cl3 C8 1.766(2) . ?
O1 C3 1.226(2) . ?
N1 C6 1.384(2) . ?
N1 C5 1.388(2) . ?
N1 C1 1.481(2) . ?
C1 C9 1.471(3) . ?
C1 C2 1.524(2) . ?
C1 H1 1.0000 . ?
O2 C6 1.349(2) . ?
O2 C7 1.430(2) . ?
C2 C3 1.512(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O3 C6 1.201(2) . ?
C3 C4 1.459(3) . ?
C4 C5 1.336(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 C8 1.516(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C10 1.195(3) . ?
C10 C11 1.439(3) . ?
C11 C12 1.394(3) . ?
C11 C16 1.397(3) . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C1 C9 -84.9(2) . . . . ?
C5 N1 C1 C9 81.90(19) . . . . ?
C6 N1 C1 C2 151.89(16) . . . . ?
C5 N1 C1 C2 -41.3(2) . . . . ?
C9 C1 C2 C3 -71.12(19) . . . . ?
N1 C1 C2 C3 51.3(2) . . . . ?
C1 C2 C3 O1 148.42(18) . . . . ?
C1 C2 C3 C4 -35.4(2) . . . . ?
O1 C3 C4 C5 -177.24(19) . . . . ?
C2 C3 C4 C5 6.7(3) . . . . ?
C3 C4 C5 N1 5.3(3) . . . . ?
C6 N1 C5 C4 -179.03(18) . . . . ?
C1 N1 C5 C4 13.7(3) . . . . ?
C7 O2 C6 O3 0.3(3) . . . . ?
C7 O2 C6 N1 -177.96(15) . . . . ?
C5 N1 C6 O3 3.4(3) . . . . ?
C1 N1 C6 O3 170.16(17) . . . . ?
C5 N1 C6 O2 -178.27(15) . . . . ?
C1 N1 C6 O2 -11.5(2) . . . . ?
C6 O2 C7 C8 -116.87(17) . . . . ?
O2 C7 C8 Cl2 -175.20(12) . . . . ?
O2 C7 C8 Cl1 -56.40(18) . . . . ?
O2 C7 C8 Cl3 65.09(18) . . . . ?
N1 C1 C9 C10 -169(4) . . . . ?
C2 C1 C9 C10 -47(4) . . . . ?
C1 C9 C10 C11 -4(6) . . . . ?
C9 C10 C11 C12 -136(3) . . . . ?
C9 C10 C11 C16 42(3) . . . . ?
C16 C11 C12 C13 -1.1(3) . . . . ?
C10 C11 C12 C13 177.06(19) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C15 C16 C11 0.7(3) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
C10 C11 C16 C15 -177.70(17) . . . . ?
