#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/28/2202896.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_2202896
loop_
_publ_author_name
'Sonar, Vijayakumar N.'
'Parkin, Sean'
'Crooks, Peter A.'
_publ_section_title
;
 2-(1-Benzyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1478
_journal_page_last               o1480
_journal_paper_doi               10.1107/S1600536803019809
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C23 H22 N2 O'
_chemical_formula_sum            'C23 H22 N2 O'
_chemical_formula_weight         342.43
_chemical_name_common
;
2-(1-Benzyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2]octan-3-one
;
_chemical_name_systematic
;
2-(1-Benzyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2]octan-3-one
;
_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                112.38(2)
_cell_angle_beta                 92.78(2)
_cell_angle_gamma                109.51(2)
_cell_formula_units_Z            2
_cell_length_a                   9.245(2)
_cell_length_b                   10.015(3)
_cell_length_c                   11.245(3)
_cell_measurement_reflns_used    26987
_cell_measurement_temperature    173.0(10)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     888.8(5)
_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 Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELXL97 and local procedures'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173.0(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  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6198
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        <1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular plate'
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.04
_refine_diff_density_max         .146
_refine_diff_density_min         -.175
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
' calc w = 1/[σ²(Fo²)+(0.0457P)²+0.2487P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1210
_reflns_number_gt                2342
_reflns_number_total             3118
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6038.cif
_cod_data_source_block           I
_cod_original_cell_volume        888.8(4)
_cod_database_code               2202896
_cod_database_fobs_code          2202896
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O 0.34682(17) -0.55464(17) -0.11645(14) 0.0435(4) Uani d . 1 . . O
N1 0.35684(19) 0.02696(19) 0.41524(16) 0.0315(4) Uani d . 1 . . N
C2 0.3181(2) -0.1281(2) 0.3371(2) 0.0301(5) Uani d . 1 . . C
H2 0.2515 -0.2116 0.3540 0.036 Uiso calc R 1 . . H
C3 0.3893(2) -0.1458(2) 0.23060(19) 0.0284(5) Uani d . 1 . . C
C4 0.4786(2) 0.0103(2) 0.2443(2) 0.0302(5) Uani d . 1 . . C
C5 0.5734(2) 0.0709(3) 0.1686(2) 0.0368(5) Uani d . 1 . . C
H5 0.5948 0.0037 0.0917 0.044 Uiso calc R 1 . . H
C6 0.6348(2) 0.2309(3) 0.2090(2) 0.0427(6) Uani d . 1 . . C
H6 0.6978 0.2734 0.1580 0.051 Uiso calc R 1 . . H
C7 0.6067(2) 0.3313(3) 0.3225(2) 0.0435(6) Uani d . 1 . . C
H7 0.6506 0.4406 0.3470 0.052 Uiso calc R 1 . . H
C8 0.5169(2) 0.2757(2) 0.4000(2) 0.0375(6) Uani d . 1 . . C
H8 0.4987 0.3443 0.4780 0.045 Uiso calc R 1 . . H
C9 0.4535(2) 0.1140(2) 0.3590(2) 0.0313(5) Uani d . 1 . . C
C10 0.3727(2) -0.2875(2) 0.1199(2) 0.0315(5) Uani d . 1 . . C
H10 0.4272 -0.2730 0.0535 0.038 Uiso calc R 1 . . H
C11 0.2918(2) -0.4367(2) 0.09660(19) 0.0306(5) Uani d . 1 . . C
N12 0.21001(19) -0.48497(19) 0.18864(16) 0.0322(4) Uani d . 1 . . N
C13 0.2871(3) -0.5760(2) 0.2253(2) 0.0368(5) Uani d . 1 . . C
H13A 0.2361 -0.6084 0.2906 0.044 Uiso calc R 1 . . H
H13B 0.3985 -0.5089 0.2666 0.044 Uiso calc R 1 . . H
C14 0.2776(3) -0.7221(3) 0.1047(2) 0.0404(6) Uani d . 1 . . C
H14A 0.3841 -0.7213 0.0972 0.048 Uiso calc R 1 . . H
H14B 0.2153 -0.8176 0.1147 0.048 Uiso calc R 1 . . H
C15 0.2001(2) -0.7220(2) -0.0193(2) 0.0369(5) Uani d . 1 . . C
H15 0.1985 -0.8114 -0.1003 0.044 Uiso calc R 1 . . H
C16 0.0331(3) -0.7291(3) -0.0051(2) 0.0431(6) Uani d . 1 . . C
H16A -0.0303 -0.8288 -0.0019 0.052 Uiso calc R 1 . . H
H16B -0.0181 -0.7229 -0.0811 0.052 Uiso calc R 1 . . H
C17 0.0454(3) -0.5898(2) 0.1233(2) 0.0402(6) Uani d . 1 . . C
H17A -0.0099 -0.5293 0.1032 0.048 Uiso calc R 1 . . H
H17B -0.0073 -0.6301 0.1841 0.048 Uiso calc R 1 . . H
C18 0.2886(2) -0.5678(2) -0.0233(2) 0.0335(5) Uani d . 1 . . C
C19 0.2832(3) 0.0897(2) 0.5234(2) 0.0353(5) Uani d . 1 . . C
H19A 0.3653 0.1766 0.5982 0.042 Uiso calc R 1 . . H
H19B 0.2301 0.0072 0.5524 0.042 Uiso calc R 1 . . H
C20 0.1650(2) 0.1487(2) 0.48625(19) 0.0283(5) Uani d . 1 . . C
C21 0.1308(2) 0.2620(2) 0.5840(2) 0.0331(5) Uani d . 1 . . C
H21 0.1815 0.3013 0.6728 0.040 Uiso calc R 1 . . H
C22 0.0229(3) 0.3182(2) 0.5530(2) 0.0385(6) Uani d . 1 . . C
H22 -0.0004 0.3954 0.6207 0.046 Uiso calc R 1 . . H
C23 -0.0505(2) 0.2628(2) 0.4249(2) 0.0392(6) Uani d . 1 . . C
H23 -0.1233 0.3025 0.4037 0.047 Uiso calc R 1 . . H
C24 -0.0176(2) 0.1489(2) 0.3270(2) 0.0364(6) Uani d . 1 . . C
H24 -0.0691 0.1092 0.2385 0.044 Uiso calc R 1 . . H
C25 0.0896(2) 0.0928(2) 0.3574(2) 0.0323(5) Uani d . 1 . . C
H25 0.1120 0.0151 0.2894 0.039 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 .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'
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
C2 N1 C9 108.68(17) y
C2 N1 C19 125.50(17) ?
C9 N1 C19 124.65(17) ?
N1 C2 C3 110.27(18) ?
N1 C2 H2 124.9 ?
C3 C2 H2 124.9 ?
C2 C3 C10 128.90(19) y
C2 C3 C4 106.13(18) ?
C10 C3 C4 124.81(18) ?
C9 C4 C5 118.95(19) ?
C9 C4 C3 106.86(17) ?
C5 C4 C3 134.2(2) ?
C6 C5 C4 118.2(2) ?
C6 C5 H5 120.9 ?
C4 C5 H5 120.9 ?
C5 C6 C7 121.7(2) ?
C5 C6 H6 119.2 ?
C7 C6 H6 119.2 ?
C8 C7 C6 121.5(2) ?
C8 C7 H7 119.3 ?
C6 C7 H7 119.3 ?
C7 C8 C9 117.1(2) ?
C7 C8 H8 121.5 ?
C9 C8 H8 121.5 ?
N1 C9 C8 129.3(2) ?
N1 C9 C4 108.05(17) ?
C8 C9 C4 122.6(2) ?
C11 C10 C3 129.6(2) y
C11 C10 H10 115.2 ?
C3 C10 H10 115.2 ?
C10 C11 N12 124.16(19) ?
C10 C11 C18 122.05(19) ?
N12 C11 C18 113.64(18) y
C11 N12 C17 109.50(16) y
C11 N12 C13 107.01(16) ?
C17 N12 C13 107.97(16) ?
N12 C13 C14 111.59(17) y
N12 C13 H13A 109.3 ?
C14 C13 H13A 109.3 ?
N12 C13 H13B 109.3 ?
C14 C13 H13B 109.3 ?
H13A C13 H13B 108.0 ?
C15 C14 C13 109.00(17) ?
C15 C14 H14A 109.9 ?
C13 C14 H14A 109.9 ?
C15 C14 H14B 109.9 ?
C13 C14 H14B 109.9 ?
H14A C14 H14B 108.3 ?
C18 C15 C14 108.17(17) ?
C18 C15 C16 106.77(17) ?
C14 C15 C16 107.92(18) ?
C18 C15 H15 111.3 ?
C14 C15 H15 111.3 ?
C16 C15 H15 111.3 ?
C15 C16 C17 108.09(18) ?
C15 C16 H16A 110.1 ?
C17 C16 H16A 110.1 ?
C15 C16 H16B 110.1 ?
C17 C16 H16B 110.1 ?
H16A C16 H16B 108.4 ?
N12 C17 C16 112.40(17) y
N12 C17 H17A 109.1 ?
C16 C17 H17A 109.1 ?
N12 C17 H17B 109.1 ?
C16 C17 H17B 109.1 ?
H17A C17 H17B 107.9 ?
O C18 C11 125.0(2) y
O C18 C15 124.0(2) y
C11 C18 C15 111.01(18) y
N1 C19 C20 112.62(16) y
N1 C19 H19A 109.1 ?
C20 C19 H19A 109.1 ?
N1 C19 H19B 109.1 ?
C20 C19 H19B 109.1 ?
H19A C19 H19B 107.8 ?
C21 C20 C25 118.87(19) ?
C21 C20 C19 119.04(18) ?
C25 C20 C19 122.09(18) ?
C20 C21 C22 120.34(19) ?
C20 C21 H21 119.8 ?
C22 C21 H21 119.8 ?
C23 C22 C21 120.4(2) ?
C23 C22 H22 119.8 ?
C21 C22 H22 119.8 ?
C22 C23 C24 119.5(2) ?
C22 C23 H23 120.2 ?
C24 C23 H23 120.2 ?
C25 C24 C23 120.3(2) ?
C25 C24 H24 119.9 ?
C23 C24 H24 119.9 ?
C24 C25 C20 120.60(19) ?
C24 C25 H25 119.7 ?
C20 C25 H25 119.7 ?
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
O C18 . 1.232(2) y
N1 C2 . 1.368(3) ?
N1 C9 . 1.383(3) y
N1 C19 . 1.456(3) y
C2 C3 . 1.376(3) ?
C2 H2 . 0.9500 ?
C3 C10 . 1.442(3) y
C3 C4 . 1.447(3) ?
C4 C9 . 1.401(3) ?
C4 C5 . 1.404(3) ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.392(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.374(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.396(3) ?
C8 H8 . 0.9500 ?
C10 C11 . 1.340(3) y
C10 H10 . 0.9500 ?
C11 N12 . 1.446(2) y
C11 C18 . 1.471(3) y
N12 C17 . 1.481(3) y
N12 C13 . 1.483(3) y
C13 C14 . 1.543(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.538(3) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C18 . 1.506(3) y
C15 C16 . 1.541(3) ?
C15 H15 . 1.0000 ?
C16 C17 . 1.545(3) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C19 C20 . 1.514(3) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 C21 . 1.385(3) ?
C20 C25 . 1.387(3) ?
C21 C22 . 1.387(3) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.374(3) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.383(3) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.378(3) ?
C24 H24 . 0.9500 ?
C25 H25 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2 N12 . 0.9500 2.5400 3.077(3) 116.00 yes
C10 H10 O . 0.9500 2.5500 2.894(3) 101.00 yes
C21 H21 O 1_566 0.9500 2.3700 3.301(3) 167.00 yes
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
C9 N1 C2 C3 0.9(2) ?
C19 N1 C2 C3 168.89(17) ?
N1 C2 C3 C10 -175.44(18) ?
N1 C2 C3 C4 0.0(2) ?
C2 C3 C4 C9 -0.9(2) ?
C10 C3 C4 C9 174.82(18) ?
C2 C3 C4 C5 -178.8(2) ?
C10 C3 C4 C5 -3.2(3) ?
C9 C4 C5 C6 -1.6(3) ?
C3 C4 C5 C6 176.1(2) ?
C4 C5 C6 C7 1.0(3) ?
C5 C6 C7 C8 0.2(3) ?
C6 C7 C8 C9 -0.7(3) ?
C2 N1 C9 C8 177.0(2) ?
C19 N1 C9 C8 8.9(3) ?
C2 N1 C9 C4 -1.4(2) ?
C19 N1 C9 C4 -169.55(17) ?
C7 C8 C9 N1 -178.21(18) ?
C7 C8 C9 C4 0.0(3) ?
C5 C4 C9 N1 179.74(16) ?
C3 C4 C9 N1 1.4(2) ?
C5 C4 C9 C8 1.2(3) ?
C3 C4 C9 C8 -177.16(18) ?
C2 C3 C10 C11 -4.4(3) y
C4 C3 C10 C11 -179.0(2) ?
C3 C10 C11 N12 -4.6(3) ?
C3 C10 C11 C18 -179.90(18) ?
C10 C11 N12 C17 127.2(2) ?
C18 C11 N12 C17 -57.1(2) ?
C10 C11 N12 C13 -116.0(2) ?
C18 C11 N12 C13 59.7(2) ?
C11 N12 C13 C14 -60.7(2) ?
C17 N12 C13 C14 57.1(2) ?
N12 C13 C14 C15 4.0(2) ?
C13 C14 C15 C18 53.7(2) ?
C13 C14 C15 C16 -61.5(2) ?
C18 C15 C16 C17 -59.7(2) ?
C14 C15 C16 C17 56.4(2) ?
C11 N12 C17 C16 53.7(2) ?
C13 N12 C17 C16 -62.4(2) ?
C15 C16 C17 N12 4.5(2) ?
C10 C11 C18 O -6.2(3) ?
N12 C11 C18 O 178.02(18) ?
C10 C11 C18 C15 175.39(18) ?
N12 C11 C18 C15 -0.4(2) ?
C14 C15 C18 O 124.6(2) ?
C16 C15 C18 O -119.5(2) ?
C14 C15 C18 C11 -57.0(2) ?
C16 C15 C18 C11 58.9(2) ?
C2 N1 C19 C20 -101.0(2) y
C9 N1 C19 C20 65.2(2) ?
N1 C19 C20 C21 -155.31(17) y
N1 C19 C20 C25 24.8(3) ?
C25 C20 C21 C22 -0.1(3) ?
C19 C20 C21 C22 -179.94(18) ?
C20 C21 C22 C23 -0.4(3) ?
C21 C22 C23 C24 0.8(3) ?
C22 C23 C24 C25 -0.9(3) ?
C23 C24 C25 C20 0.4(3) ?
C21 C20 C25 C24 0.0(3) ?
C19 C20 C25 C24 179.90(19) ?
