#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/42/2014238.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_2014238
loop_
_publ_author_name
'Sonar, Vijayakumar N.'
'Parkin, Sean'
'Crooks, Peter A.'
_publ_section_title
;(Z)-2-(1-Phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one
 and
 (Z)-(S)-2-(1-phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-ol
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o659
_journal_page_last               o661
_journal_paper_doi               10.1107/S0108270104015847
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C22 H20 N2 O3 S'
_chemical_formula_moiety         'C22 H20 N2 O3 S'
_chemical_formula_sum            'C22 H20 N2 O3 S'
_chemical_formula_weight         392.46
_chemical_name_systematic
(Z)-2-(1-Benzenesulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[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                94.5900(7)
_cell_angle_beta                 104.1170(7)
_cell_angle_gamma                110.1160(7)
_cell_formula_units_Z            2
_cell_length_a                   7.70700(10)
_cell_length_b                   10.7080(2)
_cell_length_c                   12.3080(2)
_cell_measurement_reflns_used    4073
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     909.86(3)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 1995)'
_computing_publication_material
;
SHELX97-2 (Sheldrick, 1997) and local procedures
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8085
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular wedge'
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.486
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0439P)²+0.4878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                3720
_reflns_number_total             4145
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1739.cif
_cod_data_source_block           I
_cod_database_code               2014238
_cod_database_fobs_code          2014238
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
S1 0.32935(4) 0.32107(3) 0.64002(2) 0.01552(10) Uani d . 1 . . S
O1 0.29704(15) 0.42210(10) 0.57799(8) 0.0217(2) Uani d . 1 . . O
N1 0.26764(16) 0.18446(11) 0.54245(9) 0.0160(2) Uani d . 1 . . N
O2 0.23334(13) 0.27857(10) 0.72397(7) 0.0189(2) Uani d . 1 . . O
C2 0.29258(18) 0.19292(13) 0.43398(10) 0.0157(2) Uani d . 1 . . C
H2 0.3151 0.2717 0.4004 0.019 Uiso calc R 1 . . H
C3 0.27949(17) 0.07026(12) 0.38404(10) 0.0138(2) Uani d . 1 . . C
C4 0.25055(17) -0.01966(12) 0.46554(10) 0.0137(2) Uani d . 1 . . C
C5 0.22573(18) -0.15570(13) 0.46092(11) 0.0162(2) Uani d . 1 . . C
H5 0.2275 -0.2069 0.3947 0.019 Uiso calc R 1 . . H
C6 0.19853(19) -0.21447(13) 0.55475(11) 0.0193(3) Uani d . 1 . . C
H6 0.1829 -0.3066 0.5531 0.023 Uiso calc R 1 . . H
C7 0.19377(19) -0.13993(14) 0.65217(11) 0.0197(3) Uani d . 1 . . C
H7 0.1751 -0.1828 0.7154 0.024 Uiso calc R 1 . . H
C8 0.21562(18) -0.00533(13) 0.65859(10) 0.0174(3) Uani d . 1 . . C
H8 0.2103 0.0447 0.7242 0.021 Uiso calc R 1 . . H
C9 0.24569(17) 0.05301(12) 0.56428(10) 0.0146(2) Uani d . 1 . . C
C10 0.28881(17) 0.03065(12) 0.27087(10) 0.0147(2) Uani d . 1 . . C
H10 0.2812 -0.0594 0.2529 0.018 Uiso calc R 1 . . H
C11 0.30674(17) 0.10428(12) 0.18825(10) 0.0142(2) Uani d . 1 . . C
N12 0.32003(15) 0.24292(10) 0.19814(9) 0.0149(2) Uani d . 1 . . N
C13 0.51012(19) 0.32820(13) 0.18690(10) 0.0172(3) Uani d . 1 . . C
H13A 0.6136 0.3290 0.2532 0.021 Uiso calc R 1 . . H
H13B 0.5169 0.4222 0.1870 0.021 Uiso calc R 1 . . H
C14 0.54436(19) 0.27581(13) 0.07567(11) 0.0180(3) Uani d . 1 . . C
H14A 0.5761 0.3493 0.0313 0.022 Uiso calc R 1 . . H
H14B 0.6539 0.2453 0.0944 0.022 Uiso calc R 1 . . H
C15 0.35952(18) 0.15734(12) 0.00525(10) 0.0156(3) Uani d . 1 . . C
H15 0.3744 0.1224 -0.0684 0.019 Uiso calc R 1 . . H
C16 0.1907(2) 0.20693(14) -0.01534(11) 0.0199(3) Uani d . 1 . . C
H16A 0.0702 0.1333 -0.0624 0.024 Uiso calc R 1 . . H
H16B 0.2174 0.2840 -0.0564 0.024 Uiso calc R 1 . . H
C17 0.16752(19) 0.25149(14) 0.10198(11) 0.0187(3) Uani d . 1 . . C
H17A 0.1734 0.3457 0.1083 0.022 Uiso calc R 1 . . H
H17B 0.0393 0.1931 0.1068 0.022 Uiso calc R 1 . . H
O18 0.29965(14) -0.06823(9) 0.04749(8) 0.0199(2) Uani d . 1 . . O
C18 0.31991(17) 0.04895(12) 0.07698(10) 0.0146(2) Uani d . 1 . . C
C19 0.57933(18) 0.36889(12) 0.70246(10) 0.0154(2) Uani d . 1 . . C
C20 0.7078(2) 0.45363(13) 0.65299(11) 0.0202(3) Uani d . 1 . . C
H20 0.6619 0.4867 0.5870 0.024 Uiso calc R 1 . . H
C21 0.9040(2) 0.48871(14) 0.70195(13) 0.0242(3) Uani d . 1 . . C
H21 0.9937 0.5462 0.6692 0.029 Uiso calc R 1 . . H
C22 0.9704(2) 0.44045(14) 0.79854(13) 0.0235(3) Uani d . 1 . . C
H22 1.1053 0.4654 0.8316 0.028 Uiso calc R 1 . . H
C23 0.8411(2) 0.35594(13) 0.84723(12) 0.0206(3) Uani d . 1 . . C
H23 0.8875 0.3235 0.9135 0.025 Uiso calc R 1 . . H
C24 0.64378(19) 0.31888(13) 0.79875(11) 0.0167(3) Uani d . 1 . . C
H24 0.5542 0.2602 0.8309 0.020 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'
S S 0.1246 0.1234 '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
O2 S1 O1 121.08(6) y
O2 S1 N1 106.87(6) ?
O1 S1 N1 105.68(5) y
O2 S1 C19 108.40(6) ?
O1 S1 C19 108.92(6) y
N1 S1 C19 104.68(6) y
C2 N1 C9 108.86(10) ?
C2 N1 S1 122.29(9) ?
C9 N1 S1 125.87(9) ?
C3 C2 N1 109.33(11) ?
C3 C2 H2 125.3 ?
N1 C2 H2 125.3 ?
C2 C3 C4 107.23(10) ?
C2 C3 C10 128.56(12) y
C4 C3 C10 124.20(11) ?
C5 C4 C9 119.33(11) ?
C5 C4 C3 132.58(11) ?
C9 C4 C3 108.08(11) ?
C6 C5 C4 118.65(11) ?
C6 C5 H5 120.7 ?
C4 C5 H5 120.7 ?
C5 C6 C7 120.94(12) ?
C5 C6 H6 119.5 ?
C7 C6 H6 119.5 ?
C8 C7 C6 121.64(12) ?
C8 C7 H7 119.2 ?
C6 C7 H7 119.2 ?
C7 C8 C9 116.79(12) ?
C7 C8 H8 121.6 ?
C9 C8 H8 121.6 ?
C8 C9 C4 122.62(12) ?
C8 C9 N1 130.88(11) ?
C4 C9 N1 106.44(10) ?
C11 C10 C3 128.56(12) y
C11 C10 H10 115.7 ?
C3 C10 H10 115.7 ?
C10 C11 N12 124.48(11) ?
C10 C11 C18 121.74(11) y
N12 C11 C18 113.76(10) y
C11 N12 C13 108.39(9) ?
C11 N12 C17 108.28(10) ?
C13 N12 C17 108.02(10) ?
N12 C13 C14 111.80(10) ?
N12 C13 H13A 109.3 ?
C14 C13 H13A 109.3 ?
N12 C13 H13B 109.3 ?
C14 C13 H13B 109.3 ?
H13A C13 H13B 107.9 ?
C15 C14 C13 108.66(10) ?
C15 C14 H14A 110.0 ?
C13 C14 H14A 110.0 ?
C15 C14 H14B 110.0 ?
C13 C14 H14B 110.0 ?
H14A C14 H14B 108.3 ?
C18 C15 C14 107.34(10) ?
C18 C15 C16 107.70(10) ?
C14 C15 C16 108.18(10) ?
C18 C15 H15 111.1 ?
C14 C15 H15 111.1 ?
C16 C15 H15 111.1 ?
C15 C16 C17 108.53(10) ?
C15 C16 H16A 110.0 ?
C17 C16 H16A 110.0 ?
C15 C16 H16B 110.0 ?
C17 C16 H16B 110.0 ?
H16A C16 H16B 108.4 ?
N12 C17 C16 111.85(10) ?
N12 C17 H17A 109.2 ?
C16 C17 H17A 109.2 ?
N12 C17 H17B 109.2 ?
C16 C17 H17B 109.2 ?
H17A C17 H17B 107.9 ?
O18 C18 C11 124.79(11) y
O18 C18 C15 124.77(11) ?
C11 C18 C15 110.44(10) y
C24 C19 C20 121.52(12) ?
C24 C19 S1 119.21(10) ?
C20 C19 S1 119.26(10) ?
C21 C20 C19 118.65(13) ?
C21 C20 H20 120.7 ?
C19 C20 H20 120.7 ?
C20 C21 C22 120.46(13) ?
C20 C21 H21 119.8 ?
C22 C21 H21 119.8 ?
C21 C22 C23 120.46(13) ?
C21 C22 H22 119.8 ?
C23 C22 H22 119.8 ?
C22 C23 C24 119.86(13) ?
C22 C23 H23 120.1 ?
C24 C23 H23 120.1 ?
C23 C24 C19 119.04(12) ?
C23 C24 H24 120.5 ?
C19 C24 H24 120.5 ?
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
S1 O2 . 1.4280(9) y
S1 O1 . 1.4282(10) y
S1 N1 . 1.6643(11) y
S1 C19 . 1.7609(13) y
N1 C2 . 1.4000(15) y
N1 C9 . 1.4145(16) y
C2 C3 . 1.3648(17) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.4487(17) ?
C3 C10 . 1.4493(16) y
C4 C5 . 1.3971(17) ?
C4 C9 . 1.4052(16) ?
C5 C6 . 1.3847(18) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.4016(18) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.3858(19) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.3925(17) ?
C8 H8 . 0.9500 ?
C10 C11 . 1.3404(17) y
C10 H10 . 0.9500 ?
C11 N12 . 1.4455(15) y
C11 C18 . 1.4888(16) y
N12 C13 . 1.4827(16) ?
N12 C17 . 1.4844(16) y
C13 C14 . 1.5535(17) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.5390(17) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C18 . 1.5071(17) ?
C15 C16 . 1.5408(18) ?
C15 H15 . 1.0000 ?
C16 C17 . 1.5554(17) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
O18 C18 . 1.2228(15) y
C19 C24 . 1.3912(17) ?
C19 C20 . 1.3926(18) ?
C20 C21 . 1.385(2) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.388(2) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.3889(19) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.3894(19) ?
C23 H23 . 0.9500 ?
C24 H24 . 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_publ_flag
O2 S1 N1 C2 162.86(10) ?
O1 S1 N1 C2 32.66(12) y
C19 S1 N1 C2 -82.28(11) ?
O2 S1 N1 C9 -38.89(12) y
O1 S1 N1 C9 -169.08(10) ?
C19 S1 N1 C9 75.97(11) ?
C9 N1 C2 C3 2.45(14) ?
S1 N1 C2 C3 163.95(9) ?
N1 C2 C3 C4 -1.73(14) ?
N1 C2 C3 C10 177.44(12) ?
C2 C3 C4 C5 179.22(13) ?
C10 C3 C4 C5 0.0(2) ?
C2 C3 C4 C9 0.39(14) ?
C10 C3 C4 C9 -178.83(11) ?
C9 C4 C5 C6 -0.51(18) ?
C3 C4 C5 C6 -179.25(13) ?
C4 C5 C6 C7 0.68(19) ?
C5 C6 C7 C8 0.1(2) ?
C6 C7 C8 C9 -1.01(19) ?
C7 C8 C9 C4 1.19(19) ?
C7 C8 C9 N1 178.02(12) ?
C5 C4 C9 C8 -0.44(19) ?
C3 C4 C9 C8 178.58(11) ?
C5 C4 C9 N1 -177.94(11) ?
C3 C4 C9 N1 1.07(13) ?
C2 N1 C9 C8 -179.36(13) ?
S1 N1 C9 C8 20.0(2) ?
C2 N1 C9 C4 -2.14(14) ?
S1 N1 C9 C4 -162.81(9) ?
C2 C3 C10 C11 -2.2(2) y
C4 C3 C10 C11 176.88(12) ?
C3 C10 C11 N12 -0.2(2) y
C3 C10 C11 C18 178.18(11) y
C10 C11 N12 C13 117.53(13) ?
C18 C11 N12 C13 -60.96(13) ?
C10 C11 N12 C17 -125.53(13) ?
C18 C11 N12 C17 55.99(13) ?
C11 N12 C13 C14 54.25(13) ?
C17 N12 C13 C14 -62.86(13) ?
N12 C13 C14 C15 5.19(14) ?
C13 C14 C15 C18 -59.93(13) ?
C13 C14 C15 C16 56.04(13) ?
C18 C15 C16 C17 54.57(13) ?
C14 C15 C16 C17 -61.16(13) ?
C11 N12 C17 C16 -59.83(13) ?
C13 N12 C17 C16 57.35(13) ?
C15 C16 C17 N12 4.01(15) ?
C10 C11 C18 O18 6.4(2) y
N12 C11 C18 O18 -175.02(11) y
C10 C11 C18 C15 -174.19(11) ?
N12 C11 C18 C15 4.34(14) ?
C14 C15 C18 O18 -124.84(13) ?
C16 C15 C18 O18 118.88(13) ?
C14 C15 C18 C11 55.79(13) ?
C16 C15 C18 C11 -60.48(13) ?
O2 S1 C19 C24 22.10(11) ?
O1 S1 C19 C24 155.67(10) ?
N1 S1 C19 C24 -91.68(10) ?
O2 S1 C19 C20 -159.20(10) ?
O1 S1 C19 C20 -25.64(12) ?
N1 S1 C19 C20 87.02(11) y
C24 C19 C20 C21 -0.33(19) ?
S1 C19 C20 C21 -179.00(10) ?
C19 C20 C21 C22 -0.18(19) ?
C20 C21 C22 C23 0.2(2) ?
C21 C22 C23 C24 0.3(2) ?
C22 C23 C24 C19 -0.77(19) ?
C20 C19 C24 C23 0.81(18) ?
S1 C19 C24 C23 179.47(10) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21181271
