#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/80/2208064.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_2208064
loop_
_publ_author_name
'Sonar, Vijayakumar N.'
'Parkin, Sean'
'Crooks, Peter A.'
_publ_section_title
(Z)-2-[1-(4-Methylphenylsulfonyl)-1H-indol-3-ylmethylene]-1-azabicyclo[2.2.2]octan-3-one
_journal_coeditor_code           FL6213
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o623
_journal_page_last               o625
_journal_paper_doi               10.1107/S1600536806001103
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C23 H22 N2 O3 S'
_chemical_formula_moiety         'C23 H22 N2 O3 S'
_chemical_formula_sum            'C23 H22 N2 O3 S'
_chemical_formula_weight         406.49
_chemical_name_systematic
;
(Z)-2-[1-(4-Methylbenzenesulfonyl)-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                93.2146(7)
_cell_angle_beta                 101.1313(8)
_cell_angle_gamma                107.3499(7)
_cell_formula_units_Z            2
_cell_length_a                   7.90500(10)
_cell_length_b                   10.6596(2)
_cell_length_c                   12.2642(2)
_cell_measurement_reflns_used    4384
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     960.70(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 .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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_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            8764
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.9616
_exptl_absorpt_correction_T_min  0.9524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         .290
_refine_diff_density_min         -.478
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0436P)²+0.4054P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                3686
_reflns_number_total             4419
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl6213.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (3 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (3 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2208064
_cod_database_fobs_code          2208064
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_type_symbol
N1 0.75848(16) 0.33706(11) 0.45647(9) 0.0156(2) Uani d . 1 N
C2 0.73667(18) 0.32900(13) 0.56644(11) 0.0158(3) Uani d . 1 C
H2 0.7249 0.2522 0.6039 0.019 Uiso calc R 1 H
C3 0.73486(18) 0.44827(13) 0.61186(11) 0.0151(3) Uani d . 1 C
C4 0.75212(18) 0.53632(13) 0.52570(11) 0.0146(3) Uani d . 1 C
C5 0.76136(19) 0.66935(13) 0.52469(12) 0.0176(3) Uani d . 1 C
H5 0.7541 0.7191 0.5894 0.021 Uiso calc R 1 H
C6 0.7813(2) 0.72702(14) 0.42779(12) 0.0203(3) Uani d . 1 C
H6 0.7869 0.8171 0.4258 0.024 Uiso calc R 1 H
C7 0.7933(2) 0.65424(14) 0.33249(12) 0.0210(3) Uani d . 1 C
H7 0.8060 0.6960 0.2668 0.025 Uiso calc R 1 H
C8 0.78721(19) 0.52283(14) 0.33150(12) 0.0188(3) Uani d . 1 C
H8 0.7977 0.4741 0.2672 0.023 Uiso calc R 1 H
C9 0.76501(18) 0.46575(13) 0.42917(11) 0.0156(3) Uani d . 1 C
C10 0.71856(18) 0.48549(13) 0.72375(11) 0.0161(3) Uani d . 1 C
H10 0.7088 0.5714 0.7374 0.019 Uiso calc R 1 H
C11 0.71541(18) 0.41470(13) 0.81055(11) 0.0157(3) Uani d . 1 C
N12 0.73004(16) 0.28260(11) 0.80691(9) 0.0174(3) Uani d . 1 N
C13 0.5589(2) 0.19104(14) 0.82597(12) 0.0206(3) Uani d . 1 C
H13A 0.5705 0.1014 0.8299 0.025 Uiso calc R 1 H
H13B 0.4581 0.1856 0.7620 0.025 Uiso calc R 1 H
C14 0.5131(2) 0.23735(14) 0.93547(12) 0.0213(3) Uani d . 1 C
H14A 0.3994 0.2606 0.9179 0.026 Uiso calc R 1 H
H14B 0.4951 0.1651 0.9836 0.026 Uiso calc R 1 H
C15 0.67093(19) 0.35897(13) 0.99712(11) 0.0158(3) Uani d . 1 C
H15 0.6480 0.3900 1.0697 0.019 Uiso calc R 1 H
C16 0.8470(2) 0.32136(15) 1.01569(12) 0.0203(3) Uani d . 1 C
H16A 0.8357 0.2464 1.0609 0.024 Uiso calc R 1 H
H16B 0.9506 0.3975 1.0566 0.024 Uiso calc R 1 H
C17 0.8805(2) 0.28180(14) 0.90016(11) 0.0198(3) Uani d . 1 C
H17A 0.9956 0.3443 0.8899 0.024 Uiso calc R 1 H
H17B 0.8933 0.1921 0.8982 0.024 Uiso calc R 1 H
O18 0.68521(14) 0.57662(9) 0.94411(8) 0.0204(2) Uani d . 1 O
S1 0.71705(5) 0.20360(3) 0.36585(3) 0.01588(10) Uani d . 1 S
O1 0.80640(14) 0.24847(10) 0.27801(8) 0.0207(2) Uani d . 1 O
O2 0.76104(14) 0.10600(9) 0.43094(8) 0.0195(2) Uani d . 1 O
C18 0.68934(18) 0.46512(13) 0.91986(11) 0.0155(3) Uani d . 1 C
C19 0.48100(19) 0.14954(13) 0.31137(11) 0.0156(3) Uani d . 1 C
C20 0.3683(2) 0.05641(13) 0.36278(12) 0.0190(3) Uani d . 1 C
H20 0.4177 0.0256 0.4289 0.023 Uiso calc R 1 H
C21 0.1836(2) 0.00900(14) 0.31690(12) 0.0202(3) Uani d . 1 C
H21 0.1065 -0.0543 0.3522 0.024 Uiso calc R 1 H
C22 0.1089(2) 0.05300(13) 0.21932(12) 0.0193(3) Uani d . 1 C
C23 0.2238(2) 0.14897(14) 0.17111(12) 0.0199(3) Uani d . 1 C
H23 0.1741 0.1816 0.1061 0.024 Uiso calc R 1 H
C24 0.4091(2) 0.19772(14) 0.21604(11) 0.0186(3) Uani d . 1 C
H24 0.4859 0.2631 0.1823 0.022 Uiso calc R 1 H
C25 -0.0910(2) -0.00388(15) 0.16736(13) 0.0243(3) Uani d . 1 C
H25A -0.1395 0.0679 0.1461 0.036 Uiso calc PR 0.549(19) H
H25B -0.1544 -0.0510 0.2215 0.036 Uiso calc PR 0.549(19) H
H25C -0.1091 -0.0656 0.1007 0.036 Uiso calc PR 0.549(19) H
H25D -0.1291 -0.1004 0.1661 0.036 Uiso calc PR 0.451(19) H
H25E -0.1143 0.0186 0.0907 0.036 Uiso calc PR 0.451(19) H
H25F -0.1596 0.0331 0.2115 0.036 Uiso calc PR 0.451(19) 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'
S S .1246 .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
C2 N1 C9 108.74(11) ?
C2 N1 S1 122.57(9) ?
C9 N1 S1 126.12(9) ?
C3 C2 N1 109.57(12) ?
C3 C2 H2 125.2 ?
N1 C2 H2 125.2 ?
C2 C3 C10 128.47(12) y
C2 C3 C4 107.14(12) ?
C10 C3 C4 124.39(12) y
C5 C4 C9 119.30(12) ?
C5 C4 C3 132.66(13) ?
C9 C4 C3 108.03(12) ?
C6 C5 C4 118.74(13) ?
C6 C5 H5 120.6 ?
C4 C5 H5 120.6 ?
C5 C6 C7 120.82(13) ?
C5 C6 H6 119.6 ?
C7 C6 H6 119.6 ?
C8 C7 C6 121.75(13) ?
C8 C7 H7 119.1 ?
C6 C7 H7 119.1 ?
C7 C8 C9 116.77(13) ?
C7 C8 H8 121.6 ?
C9 C8 H8 121.6 ?
C8 C9 C4 122.63(12) ?
C8 C9 N1 130.84(13) ?
C4 C9 N1 106.49(11) ?
C11 C10 C3 128.49(13) y
C11 C10 H10 115.8 ?
C3 C10 H10 115.8 ?
C10 C11 N12 124.13(12) ?
C10 C11 C18 122.02(12) y
N12 C11 C18 113.82(11) y
C11 N12 C13 108.27(11) ?
C11 N12 C17 108.27(11) ?
C13 N12 C17 108.07(11) ?
N12 C13 C14 111.73(11) ?
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 108.87(11) ?
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 107.10(11) ?
C18 C15 C16 107.71(11) ?
C14 C15 C16 108.26(12) ?
C18 C15 H15 111.2 ?
C14 C15 H15 111.2 ?
C16 C15 H15 111.2 ?
C15 C16 C17 108.67(11) ?
C15 C16 H16A 110.0 ?
C17 C16 H16A 110.0 ?
C15 C16 H16B 110.0 ?
C17 C16 H16B 110.0 ?
H16A C16 H16B 108.3 ?
N12 C17 C16 111.94(11) ?
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 ?
O1 S1 O2 121.41(6) y
O1 S1 N1 106.10(6) y
O2 S1 N1 105.82(6) y
O1 S1 C19 108.58(6) ?
O2 S1 C19 108.14(6) ?
N1 S1 C19 105.73(6) y
O18 C18 C11 125.05(13) y
O18 C18 C15 124.70(12) ?
C11 C18 C15 110.24(11) y
C20 C19 C24 120.64(13) ?
C20 C19 S1 119.45(11) ?
C24 C19 S1 119.89(11) ?
C21 C20 C19 119.53(13) ?
C21 C20 H20 120.2 ?
C19 C20 H20 120.2 ?
C20 C21 C22 120.87(13) ?
C20 C21 H21 119.6 ?
C22 C21 H21 119.6 ?
C23 C22 C21 118.53(13) ?
C23 C22 C25 121.13(13) ?
C21 C22 C25 120.34(13) ?
C24 C23 C22 121.35(13) ?
C24 C23 H23 119.3 ?
C22 C23 H23 119.3 ?
C23 C24 C19 119.03(13) ?
C23 C24 H24 120.5 ?
C19 C24 H24 120.5 ?
C22 C25 H25A 109.5 ?
C22 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
C22 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
C22 C25 H25D 109.5 ?
H25A C25 H25D 141.1 ?
H25B C25 H25D 56.3 ?
H25C C25 H25D 56.3 ?
C22 C25 H25E 109.5 ?
H25A C25 H25E 56.3 ?
H25B C25 H25E 141.1 ?
H25C C25 H25E 56.3 ?
H25D C25 H25E 109.5 ?
C22 C25 H24F 109.5 ?
H25A C25 H25F 56.3 ?
H25B C25 H25F 56.3 ?
H25C C25 H25F 141.1 ?
H25D C25 H25F 109.5 ?
H25E C25 H25F 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.3965(17) y
N1 C9 1.4186(17) ?
N1 S1 1.6646(11) y
C2 C3 1.3643(19) y
C2 H2 0.9500 ?
C3 C10 1.4474(19) y
C3 C4 1.4514(18) ?
C4 C5 1.3989(19) ?
C4 C9 1.4037(19) ?
C5 C6 1.383(2) ?
C5 H5 0.9500 ?
C6 C7 1.401(2) ?
C6 H6 0.9500 ?
C7 C8 1.386(2) ?
C7 H7 0.9500 ?
C8 C9 1.3911(19) ?
C8 H8 0.9500 ?
C10 C11 1.3388(19) y
C10 H10 0.9500 ?
C11 N12 1.4458(17) ?
C11 C18 1.4901(18) y
N12 C13 1.4825(18) ?
N12 C17 1.4846(18) ?
C13 C14 1.549(2) ?
C13 H13A 0.9900 ?
C13 H13B 0.9900 ?
C14 C15 1.5395(19) ?
C14 H14A 0.9900 ?
C14 H14B 0.9900 ?
C15 C18 1.5082(18) ?
C15 C16 1.540(2) ?
C15 H15 1.0000 ?
C16 C17 1.5490(19) ?
C16 H16A 0.9900 ?
C16 H16B 0.9900 ?
C17 H17A 0.9900 ?
C17 H17B 0.9900 ?
O18 C18 1.2204(16) y
S1 O1 1.4276(10) y
S1 O2 1.4291(10) ?
S1 C19 1.7591(14) ?
C19 C20 1.3917(19) ?
C19 C24 1.3923(19) ?
C20 C21 1.384(2) ?
C20 H20 0.9500 ?
C21 C22 1.399(2) ?
C21 H21 0.9500 ?
C22 C23 1.394(2) ?
C22 C25 1.505(2) ?
C23 C24 1.386(2) ?
C23 H23 0.9500 ?
C24 H24 0.9500 ?
C25 H25A 0.9800 ?
C25 H25B 0.9800 ?
C25 H25C 0.9800 ?
C25 H25D 0.9800 ?
C25 H25E 0.9800 ?
C25 H25F 0.9800 ?
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 -1.95(15) ?
S1 N1 C2 C3 -164.74(10) ?
N1 C2 C3 C10 -178.82(13) ?
N1 C2 C3 C4 1.38(15) ?
C2 C3 C4 C5 -178.70(15) ?
C10 C3 C4 C5 1.5(2) ?
C2 C3 C4 C9 -0.31(15) ?
C10 C3 C4 C9 179.88(12) ?
C9 C4 C5 C6 0.6(2) ?
C3 C4 C5 C6 178.83(14) ?
C4 C5 C6 C7 -0.4(2) ?
C5 C6 C7 C8 -0.5(2) ?
C6 C7 C8 C9 1.2(2) ?
C7 C8 C9 C4 -1.0(2) ?
C7 C8 C9 N1 -178.04(13) ?
C5 C4 C9 C8 0.1(2) ?
C3 C4 C9 C8 -178.49(13) ?
C5 C4 C9 N1 177.79(12) ?
C3 C4 C9 N1 -0.85(15) ?
C2 N1 C9 C8 179.07(14) ?
S1 N1 C9 C8 -18.9(2) ?
C2 N1 C9 C4 1.69(15) ?
S1 N1 C9 C4 163.71(10) ?
C2 C3 C10 C11 5.6(2) y
C4 C3 C10 C11 -174.65(14) ?
C3 C10 C11 N12 0.6(2) ?
C3 C10 C11 C18 -177.18(13) ?
C10 C11 N12 C13 -116.89(15) ?
C18 C11 N12 C13 61.01(14) ?
C10 C11 N12 C17 126.17(14) ?
C18 C11 N12 C17 -55.93(15) ?
C11 N12 C13 C14 -54.33(15) ?
C17 N12 C13 C14 62.74(15) ?
N12 C13 C14 C15 -5.24(17) ?
C13 C14 C15 C18 60.16(15) ?
C13 C14 C15 C16 -55.73(15) ?
C18 C15 C16 C17 -54.77(14) ?
C14 C15 C16 C17 60.72(14) ?
C11 N12 C17 C16 59.65(15) ?
C13 N12 C17 C16 -57.41(15) ?
C15 C16 C17 N12 -3.80(16) ?
C2 N1 S1 O1 -162.15(11) y
C9 N1 S1 O1 38.15(13) ?
C2 N1 S1 O2 -31.94(13) y
C9 N1 S1 O2 168.36(11) ?
C2 N1 S1 C19 82.64(12) ?
C9 N1 S1 C19 -77.06(12) ?
C10 C11 C18 O18 -6.9(2) y
N12 C11 C18 O18 175.12(13) ?
C10 C11 C18 C15 173.74(13) ?
N12 C11 C18 C15 -4.21(16) ?
C14 C15 C18 O18 124.77(14) ?
C16 C15 C18 O18 -118.97(15) ?
C14 C15 C18 C11 -55.90(14) ?
C16 C15 C18 C11 60.36(14) ?
O1 S1 C19 C20 154.83(11) ?
O2 S1 C19 C20 21.30(13) ?
N1 S1 C19 C20 -91.68(12) y
O1 S1 C19 C24 -23.68(13) ?
O2 S1 C19 C24 -157.21(11) ?
N1 S1 C19 C24 89.81(12) ?
C24 C19 C20 C21 1.6(2) ?
S1 C19 C20 C21 -176.89(11) ?
C19 C20 C21 C22 0.3(2) ?
C20 C21 C22 C23 -2.0(2) ?
C20 C21 C22 C25 177.24(13) ?
C21 C22 C23 C24 1.9(2) ?
C25 C22 C23 C24 -177.33(13) ?
C22 C23 C24 C19 -0.1(2) ?
C20 C19 C24 C23 -1.7(2) ?
S1 C19 C24 C23 176.78(10) ?
