#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:13:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178426 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/47/4024771.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_4024771
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            'C24 H26 Cl3 N O3'
_chemical_formula_weight         482.81
_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                82.0450(7)
_cell_angle_beta                 88.7559(7)
_cell_angle_gamma                66.1562(7)
_cell_formula_units_Z            2
_cell_length_a                   9.97360(10)
_cell_length_b                   11.1618(2)
_cell_length_c                   11.5289(2)
_cell_measurement_reflns_used    5249
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1161.77(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      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full .998
_diffrn_measured_fraction_theta_max .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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10487
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  0.9206
_exptl_absorpt_correction_T_min  0.8842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         .294
_refine_diff_density_min         -.273
_refine_diff_density_rms         .055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0361
_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)+(0.0435P)²+0.3297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0940
_reflns_number_gt                4182
_reflns_number_total             5279
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo901082r_si_002.cif
_cod_data_source_block           k05011
_cod_database_code               4024771
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
N1 N 0.19440(14) 0.20123(12) 0.27348(11) 0.0164(3) Uani 1 1 d . . .
O1 O 0.17947(12) 0.45499(12) -0.02504(10) 0.0260(3) Uani 1 1 d . . .
O2 O 0.17483(13) 0.01169(11) 0.35707(9) 0.0230(3) Uani 1 1 d . . .
O3 O 0.21027(12) 0.14792(10) 0.46967(9) 0.0187(2) Uani 1 1 d . . .
C1 C 0.21519(16) 0.32245(15) 0.28939(13) 0.0172(3) Uani 1 1 d . . .
H1 H 0.1578 0.3578 0.3584 0.021 Uiso 1 1 calc R . .
C2 C 0.14997(17) 0.42828(15) 0.18194(13) 0.0198(3) Uani 1 1 d . . .
H2A H 0.0417 0.4640 0.1841 0.024 Uiso 1 1 calc R . .
H2B H 0.1796 0.5020 0.1874 0.024 Uiso 1 1 calc R . .
C3 C 0.19586(16) 0.37930(16) 0.06531(14) 0.0193(3) Uani 1 1 d . . .
C4 C 0.25829(17) 0.23161(16) 0.06892(13) 0.0190(3) Uani 1 1 d . . .
H4A H 0.3636 0.1936 0.0930 0.023 Uiso 1 1 calc R . .
H4B H 0.2499 0.2100 -0.0103 0.023 Uiso 1 1 calc R . .
C5 C 0.17677(17) 0.17086(15) 0.15509(13) 0.0173(3) Uani 1 1 d . . .
H5 H 0.2246 0.0726 0.1575 0.021 Uiso 1 1 calc R . .
C6 C 0.01424(17) 0.21629(16) 0.12204(13) 0.0178(3) Uani 1 1 d . . .
H6A H -0.0295 0.1700 0.1802 0.021 Uiso 1 1 calc R . .
H6B H -0.0367 0.3123 0.1256 0.021 Uiso 1 1 calc R . .
C7 C -0.01093(17) 0.18969(17) 0.00011(14) 0.0209(3) Uani 1 1 d . . .
H7A H 0.0247 0.2431 -0.0580 0.025 Uiso 1 1 calc R . .
H7B H 0.0493 0.0953 -0.0055 0.025 Uiso 1 1 calc R . .
C8 C -0.16827(17) 0.21984(15) -0.03309(13) 0.0174(3) Uani 1 1 d . . .
C9 C -0.28676(17) 0.29553(16) 0.02821(14) 0.0199(3) Uani 1 1 d . . .
H9 H -0.2699 0.3296 0.0949 0.024 Uiso 1 1 calc R . .
C10 C -0.42994(18) 0.32209(16) -0.00682(14) 0.0220(3) Uani 1 1 d . . .
H10 H -0.5097 0.3738 0.0362 0.026 Uiso 1 1 calc R . .
C11 C -0.45676(18) 0.27358(16) -0.10382(14) 0.0219(3) Uani 1 1 d . . .
H11 H -0.5544 0.2907 -0.1271 0.026 Uiso 1 1 calc R . .
C12 C -0.33956(18) 0.19961(16) -0.16675(14) 0.0233(4) Uani 1 1 d . . .
H12 H -0.3570 0.1669 -0.2341 0.028 Uiso 1 1 calc R . .
C13 C -0.19729(18) 0.17315(16) -0.13195(14) 0.0206(3) Uani 1 1 d . . .
H13 H -0.1180 0.1224 -0.1759 0.025 Uiso 1 1 calc R . .
C14 C 0.37597(16) 0.29405(15) 0.31675(14) 0.0183(3) Uani 1 1 d . . .
H14A H 0.4296 0.2866 0.2430 0.022 Uiso 1 1 calc R . .
H14B H 0.4217 0.2083 0.3685 0.022 Uiso 1 1 calc R . .
C15 C 0.39004(18) 0.40317(17) 0.37669(16) 0.0259(4) Uani 1 1 d . . .
H15A H 0.3368 0.4898 0.3279 0.031 Uiso 1 1 calc R . .
H15B H 0.3432 0.4055 0.4534 0.031 Uiso 1 1 calc R . .
C16 C 0.54734(17) 0.38275(15) 0.39544(14) 0.0194(3) Uani 1 1 d . . .
C17 C 0.61377(19) 0.44251(17) 0.31387(14) 0.0261(4) Uani 1 1 d . . .
H17 H 0.5596 0.4956 0.2450 0.031 Uiso 1 1 calc R . .
C18 C 0.7574(2) 0.42640(18) 0.33073(15) 0.0291(4) Uani 1 1 d . . .
H18 H 0.8007 0.4688 0.2742 0.035 Uiso 1 1 calc R . .
C19 C 0.83766(18) 0.34832(17) 0.43020(16) 0.0267(4) Uani 1 1 d . . .
H19 H 0.9361 0.3373 0.4424 0.032 Uiso 1 1 calc R . .
C20 C 0.77434(18) 0.28643(16) 0.51174(15) 0.0258(4) Uani 1 1 d . . .
H20 H 0.8297 0.2317 0.5795 0.031 Uiso 1 1 calc R . .
C21 C 0.62983(18) 0.30419(16) 0.49456(15) 0.0228(4) Uani 1 1 d . . .
H21 H 0.5867 0.2620 0.5514 0.027 Uiso 1 1 calc R . .
C22 C 0.19116(16) 0.11245(15) 0.36431(13) 0.0177(3) Uani 1 1 d . . .
C23 C 0.20903(18) 0.05510(16) 0.56816(13) 0.0202(3) Uani 1 1 d . . .
H23A H 0.2760 -0.0359 0.5565 0.024 Uiso 1 1 calc R . .
H23B H 0.1089 0.0583 0.5785 0.024 Uiso 1 1 calc R . .
C24 C 0.25950(17) 0.09394(16) 0.67413(13) 0.0204(3) Uani 1 1 d . . .
Cl1 Cl 0.43905(5) 0.08806(4) 0.65678(4) 0.03013(12) Uani 1 1 d . . .
Cl2 Cl 0.13926(5) 0.25565(4) 0.69801(4) 0.03371(13) Uani 1 1 d . . .
Cl3 Cl 0.26119(5) -0.02190(4) 0.79665(3) 0.02629(11) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .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
C22 N1 C5 116.08(12) . . ?
C22 N1 C1 122.68(12) . . ?
C5 N1 C1 121.24(12) . . ?
C22 O3 C23 113.39(12) . . ?
N1 C1 C14 112.47(12) . . ?
N1 C1 C2 109.70(12) . . ?
C14 C1 C2 112.46(13) . . ?
N1 C1 H1 107.3 . . ?
C14 C1 H1 107.3 . . ?
C2 C1 H1 107.3 . . ?
C3 C2 C1 114.52(13) . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
O1 C3 C4 122.73(15) . . ?
O1 C3 C2 121.90(15) . . ?
C4 C3 C2 115.33(13) . . ?
C3 C4 C5 110.56(13) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C4 108.60(12) . . ?
N1 C5 C6 110.43(12) . . ?
C4 C5 C6 114.02(12) . . ?
N1 C5 H5 107.9 . . ?
C4 C5 H5 107.9 . . ?
C6 C5 H5 107.9 . . ?
C7 C6 C5 112.83(13) . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 115.38(13) . . ?
C8 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C13 118.03(14) . . ?
C9 C8 C7 123.03(13) . . ?
C13 C8 C7 118.91(14) . . ?
C8 C9 C10 120.88(14) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 120.41(15) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.25(15) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 120.36(15) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C8 121.06(15) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C1 C14 C15 111.85(12) . . ?
C1 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C1 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 112.63(13) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C21 118.10(15) . . ?
C17 C16 C15 120.67(15) . . ?
C21 C16 C15 121.23(15) . . ?
C18 C17 C16 121.36(16) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C19 C18 C17 119.75(16) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 119.85(16) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 119.96(15) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 120.98(16) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
O2 C22 N1 125.80(14) . . ?
O2 C22 O3 122.35(14) . . ?
N1 C22 O3 111.85(13) . . ?
O3 C23 C24 106.77(12) . . ?
O3 C23 H23A 110.4 . . ?
C24 C23 H23A 110.4 . . ?
O3 C23 H23B 110.4 . . ?
C24 C23 H23B 110.4 . . ?
H23A C23 H23B 108.6 . . ?
C23 C24 Cl1 110.80(11) . . ?
C23 C24 Cl2 111.11(11) . . ?
Cl1 C24 Cl2 108.91(9) . . ?
C23 C24 Cl3 107.26(11) . . ?
Cl1 C24 Cl3 109.05(8) . . ?
Cl2 C24 Cl3 109.68(8) . . ?
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
N1 C22 1.3478(19) . ?
N1 C5 1.4817(18) . ?
N1 C1 1.4848(19) . ?
O1 C3 1.2156(18) . ?
O2 C22 1.2137(19) . ?
O3 C22 1.3685(17) . ?
O3 C23 1.4307(18) . ?
C1 C14 1.535(2) . ?
C1 C2 1.537(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.513(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.503(2) . ?
C4 C5 1.527(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.529(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.523(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.512(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.390(2) . ?
C8 C13 1.398(2) . ?
C9 C10 1.393(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.535(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.507(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.387(2) . ?
C16 C21 1.390(2) . ?
C17 C18 1.384(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C23 C24 1.511(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 Cl1 1.7732(17) . ?
C24 Cl2 1.7734(16) . ?
C24 Cl3 1.7736(16) . ?
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
C22 N1 C1 C14 78.22(18) . . . . ?
C5 N1 C1 C14 -101.41(15) . . . . ?
C22 N1 C1 C2 -155.82(14) . . . . ?
C5 N1 C1 C2 24.56(18) . . . . ?
N1 C1 C2 C3 -48.67(17) . . . . ?
C14 C1 C2 C3 77.29(16) . . . . ?
C1 C2 C3 O1 -164.25(14) . . . . ?
C1 C2 C3 C4 17.55(19) . . . . ?
O1 C3 C4 C5 -140.39(15) . . . . ?
C2 C3 C4 C5 37.79(17) . . . . ?
C22 N1 C5 C4 -150.88(13) . . . . ?
C1 N1 C5 C4 28.77(18) . . . . ?
C22 N1 C5 C6 83.42(16) . . . . ?
C1 N1 C5 C6 -96.93(16) . . . . ?
C3 C4 C5 N1 -60.78(16) . . . . ?
C3 C4 C5 C6 62.80(16) . . . . ?
N1 C5 C6 C7 179.05(13) . . . . ?
C4 C5 C6 C7 56.46(18) . . . . ?
C5 C6 C7 C8 174.17(13) . . . . ?
C6 C7 C8 C9 15.2(2) . . . . ?
C6 C7 C8 C13 -166.81(14) . . . . ?
C13 C8 C9 C10 1.1(2) . . . . ?
C7 C8 C9 C10 179.10(15) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
C10 C11 C12 C13 0.9(2) . . . . ?
C11 C12 C13 C8 0.1(2) . . . . ?
C9 C8 C13 C12 -1.0(2) . . . . ?
C7 C8 C13 C12 -179.16(15) . . . . ?
N1 C1 C14 C15 -158.80(13) . . . . ?
C2 C1 C14 C15 76.74(17) . . . . ?
C1 C14 C15 C16 -175.35(14) . . . . ?
C14 C15 C16 C17 93.87(19) . . . . ?
C14 C15 C16 C21 -86.30(19) . . . . ?
C21 C16 C17 C18 -0.9(2) . . . . ?
C15 C16 C17 C18 178.97(15) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C21 -0.9(3) . . . . ?
C19 C20 C21 C16 0.6(2) . . . . ?
C17 C16 C21 C20 0.3(2) . . . . ?
C15 C16 C21 C20 -179.57(15) . . . . ?
C5 N1 C22 O2 -0.2(2) . . . . ?
C1 N1 C22 O2 -179.87(14) . . . . ?
C5 N1 C22 O3 179.16(12) . . . . ?
C1 N1 C22 O3 -0.48(19) . . . . ?
C23 O3 C22 O2 0.0(2) . . . . ?
C23 O3 C22 N1 -179.37(12) . . . . ?
C22 O3 C23 C24 169.48(12) . . . . ?
O3 C23 C24 Cl1 -60.21(14) . . . . ?
O3 C23 C24 Cl2 61.01(15) . . . . ?
O3 C23 C24 Cl3 -179.13(10) . . . . ?
