#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/68/2206839.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_2206839
loop_
_publ_author_name
'Sonar, Vijayakumar N.'
'Parkin, Sean'
'Crooks, Peter A.'
_publ_section_title
(2E,4E)-8-Methyl-2,4-bis(3-thienylmethylene)-8-azabicyclo[3.2.1]octan-3-one
_journal_coeditor_code           AC6202
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3445
_journal_page_last               o3446
_journal_paper_doi               10.1107/S160053680503028X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C18 H17 N O S2'
_chemical_formula_moiety         'C18 H17 N O S2'
_chemical_formula_sum            'C18 H17 N O S2'
_chemical_formula_weight         327.45
_chemical_name_systematic
(2E,4E)-8-Methyl-2,4-bis-thiophen-3-ylmethylene-8-azabicyclo[3.2.1]octan-3-one
_space_group_IT_number           36
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.3783(4)
_cell_length_b                   10.5680(6)
_cell_length_c                   7.3257(3)
_cell_measurement_reflns_used    994
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1500.23(11)
_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  'SHELXL97 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 area-detector'
_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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1668
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.9164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(SCALEPACK, Version 0.95.373; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular fragment'
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.196
_refine_ls_abs_structure_details 'Flack (1983), with how many Friedel pairs'
_refine_ls_abs_structure_Flack   0.47(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1668
_refine_ls_number_restraints     186
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0313
_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)+(0.0376P)²+0.3768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0738
_reflns_number_gt                1551
_reflns_number_total             1668
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6202.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'C 2c -2 '
_cod_database_code               2206839
_cod_database_fobs_code          2206839
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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
O1 1.0000 1.04922(15) 0.7913(3) 0.0239(4) Uani d SU 1 . . O
N1 1.0000 0.67138(18) 0.8054(3) 0.0157(4) Uani d SU 1 . . N
C1 1.0000 0.9364(2) 0.7552(3) 0.0165(5) Uani d SU 1 . . C
C2 0.93431(8) 0.86450(14) 0.7290(3) 0.0155(3) Uani d U 1 B . C
C3 0.94082(8) 0.72283(14) 0.7042(3) 0.0152(3) Uani d U 1 . . C
H3 0.8972 0.6795 0.7421 0.018 Uiso calc R 1 . . H
C4 0.95997(8) 0.68646(16) 0.5066(3) 0.0182(4) Uani d U 1 . . C
H4A 0.9417 0.7492 0.4186 0.022 Uiso calc R 1 . . H
H4B 0.9417 0.6018 0.4751 0.022 Uiso calc R 1 . . H
C5 1.0000 0.6941(2) 1.0032(3) 0.0201(5) Uani d SU 1 . . C
H5A 0.9933 0.7846 1.0268 0.030 Uiso calc PR 0.50 . . H
H5B 1.0442 0.6669 1.0549 0.030 Uiso calc PR 0.50 . . H
H5C 0.9625 0.6460 1.0599 0.030 Uiso calc PR 0.50 . . H
C6 0.87556(8) 0.93268(15) 0.7284(2) 0.0160(3) Uani d U 1 . . C
H6 0.8813 1.0203 0.7532 0.019 Uiso calc R 1 A 1 H
C7 0.80459(7) 0.89298(15) 0.6955(3) 0.0144(3) Uani d PDU 0.604(2) B 1 C
C8 0.7817(6) 0.7892(12) 0.607(3) 0.0135(13) Uani d PDU 0.604(2) B 1 C
H8 0.8119 0.7276 0.5566 0.016 Uiso calc PR 0.604(2) B 1 H
S1 0.69352(6) 0.77756(15) 0.5917(2) 0.0162(3) Uani d PDU 0.604(2) B 1 S
C9 0.6851(4) 0.9185(10) 0.7108(17) 0.0176(16) Uani d PDU 0.604(2) B 1 C
H9 0.6420 0.9539 0.7448 0.021 Uiso calc PR 0.604(2) B 1 H
C10 0.7459(4) 0.9719(11) 0.7496(19) 0.0136(12) Uani d PDU 0.604(2) B 1 C
H10 0.7505 1.0523 0.8062 0.016 Uiso calc PR 0.604(2) B 1 H
C7' 0.80459(7) 0.89298(15) 0.6955(3) 0.0144(3) Uani d PDU 0.396(2) B 2 C
C8' 0.7535(6) 0.9653(16) 0.754(3) 0.0143(18) Uani d PDU 0.396(2) B 2 C
H8' 0.7607 1.0396 0.8246 0.017 Uiso calc PR 0.396(2) B 2 H
S1' 0.67364(15) 0.9136(4) 0.6918(6) 0.0170(5) Uani d PDU 0.396(2) B 2 S
C9' 0.7115(4) 0.7811(11) 0.593(2) 0.0203(18) Uani d PDU 0.396(2) B 2 C
H9' 0.6852 0.7156 0.5374 0.024 Uiso calc PR 0.396(2) B 2 H
C10' 0.7801(9) 0.7786(19) 0.600(4) 0.0135(18) Uani d PDU 0.396(2) B 2 C
H10' 0.8087 0.7136 0.5522 0.016 Uiso calc PR 0.396(2) B 2 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C3 . 3_755 115.92(13) ?
C5 N1 C3 . . 115.92(13) ?
C3 N1 C3 3_755 . 102.55(18) ?
O1 C1 C2 . 3_755 121.63(9) ?
O1 C1 C2 . . 121.62(9) y
C2 C1 C2 3_755 . 116.72(19) ?
C6 C2 C1 . . 116.60(15) y
C6 C2 C3 . . 126.81(14) ?
C1 C2 C3 . . 116.58(14) ?
N1 C3 C2 . . 111.75(15) ?
N1 C3 C4 . . 101.15(13) ?
C2 C3 C4 . . 112.28(14) ?
N1 C3 H3 . . 110.4 ?
C2 C3 H3 . . 110.4 ?
C4 C3 H3 . . 110.4 ?
C3 C4 C4 . 3_755 103.92(8) ?
C3 C4 H4A . . 111.0 ?
C4 C4 H4A 3_755 . 111.0 ?
C3 C4 H4B . . 111.0 ?
C4 C4 H4B 3_755 . 111.0 ?
H4A C4 H4B . . 109.0 ?
N1 C5 H5A . . 109.5 ?
N1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
N1 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C2 C6 C7 . . 130.07(14) y
C2 C6 H6 . . 115.0 ?
C7 C6 H6 . . 115.0 ?
C8 C7 C6 . . 128.6(5) y
C8 C7 C10 . . 109.7(4) ?
C6 C7 C10 . . 121.6(4) ?
C7 C8 S1 . . 114.6(7) y
C7 C8 H8 . . 122.7 ?
S1 C8 H8 . . 122.7 ?
C8 S1 C9 . . 90.0(4) y
C10 C9 S1 . . 112.8(7) ?
C10 C9 H9 . . 123.6 ?
S1 C9 H9 . . 123.6 ?
C9 C10 C7 . . 112.7(8) ?
C9 C10 H10 . . 123.7 ?
C7 C10 H10 . . 123.7 ?
S1' C8' H8' . . 123.0 ?
C8' S1' C9' . . 89.2(6) ?
C10' C9' S1' . . 114.8(9) ?
C10' C9' H9' . . 122.6 ?
S1' C9' H9' . . 122.6 ?
C9' C10' H10' . . 125.5 ?
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
O1 C1 . 1.221(3) y
N1 C5 . 1.469(3) y
N1 C3 3_755 1.470(2) ?
N1 C3 . 1.470(2) y
C1 C2 3_755 1.4951(19) ?
C1 C2 . 1.4952(19) y
C2 C6 . 1.347(2) y
C2 C3 . 1.513(2) y
C3 C4 . 1.543(3) y
C3 H3 . 1.0000 ?
C4 C4 3_755 1.552(3) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 C7 . 1.458(2) y
C6 H6 . 0.9500 ?
C7 C8 . 1.350(10) ?
C7 C10 . 1.465(8) ?
C8 S1 . 1.716(11) y
C8 H8 . 0.9500 ?
S1 C9 . 1.733(9) y
C9 C10 . 1.337(12) ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C8' S1' . 1.704(14) ?
C8' H8' . 0.9500 ?
S1' C9' . 1.740(10) ?
C9' C10' . 1.331(18) ?
C9' H9' . 0.9500 ?
C10' H10' . 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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C6 . . 6.6(3) y
C2 C1 C2 C6 3_755 . -171.36(13) ?
O1 C1 C2 C3 . . -173.9(2) y
C2 C1 C2 C3 3_755 . 8.1(3) ?
C5 N1 C3 C2 . . 58.0(2) ?
C3 N1 C3 C2 3_755 . -69.3(2) ?
C5 N1 C3 C4 . . 177.69(15) ?
C3 N1 C3 C4 3_755 . 50.38(18) ?
C6 C2 C3 N1 . . -148.89(17) ?
C1 C2 C3 N1 . . 31.7(2) ?
C6 C2 C3 C4 . . 98.2(2) ?
C1 C2 C3 C4 . . -81.18(19) ?
N1 C3 C4 C4 . 3_755 -29.76(11) ?
C2 C3 C4 C4 . 3_755 89.51(11) ?
C1 C2 C6 C7 . . 175.88(18) ?
C3 C2 C6 C7 . . -3.5(3) ?
C2 C6 C7 C8 . . -21.6(12) y
C2 C6 C7 C10 . . 162.7(7) y
C6 C7 C8 S1 . . -178.5(5) ?
C10 C7 C8 S1 . . -2.3(17) ?
C7 C8 S1 C9 . . -0.2(14) ?
C8 S1 C9 C10 . . 2.9(13) ?
S1 C9 C10 C7 . . -4.8(15) ?
C8 C7 C10 C9 . . 4.6(17) ?
C6 C7 C10 C9 . . -178.9(9) ?
C8' S1' C9' C10' . . -2(2) ?
