#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/15/2211573.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_2211573
loop_
_publ_author_name
'Sonar, Vijayakumar N.'
'M. Venkataraj'
'Parkin, Sean'
'Crooks, Peter A.'
_publ_section_title
;
 (Z)-2-(4-Methylbenzylidene)-1-azabicyclo[2.2.2]octan-3-one
;
_journal_coeditor_code           OM2071
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5740
_journal_page_last               o5741
_journal_paper_doi               10.1107/S1600536806048963
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H17 N O'
_chemical_formula_moiety         'C15 H17 N O'
_chemical_formula_sum            'C15 H17 N O'
_chemical_formula_weight         227.30
_chemical_name_systematic
;
(Z)-2-(4-Methylbenzylidene)-1-azabicyclo[2.2.2]octan-3-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   5.8527(2)
_cell_length_b                   9.9840(3)
_cell_length_c                   20.3309(6)
_cell_measurement_reflns_used    1619
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1188.00(6)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            2724
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0474
_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)+(0.0819P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                1262
_reflns_number_total             1602
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2071.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_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.

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

The following automatic conversions were performed:

'_geom_bond_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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2211573
_cod_database_fobs_code          2211573
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_type_symbol
_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
C C1 0.5858(4) 0.5276(2) 0.38226(11) 0.0167(5) Uani d . 1
C C2 0.4250(4) 0.6220(2) 0.36096(11) 0.0191(5) Uani d . 1
H H2 0.2886 0.6353 0.3854 0.023 Uiso calc R 1
C C3 0.4638(5) 0.6959(2) 0.30453(12) 0.0220(6) Uani d . 1
H H3 0.3518 0.7585 0.2905 0.026 Uiso calc R 1
C C4 0.6636(4) 0.6809(2) 0.26760(11) 0.0202(6) Uani d . 1
C C5 0.8206(5) 0.5861(2) 0.28855(11) 0.0214(6) Uani d . 1
H H5 0.9571 0.5735 0.2640 0.026 Uiso calc R 1
C C6 0.7839(5) 0.5088(2) 0.34456(11) 0.0190(6) Uani d . 1
H H6 0.8931 0.4434 0.3573 0.023 Uiso calc R 1
C C7 0.5558(5) 0.4446(2) 0.44123(11) 0.0172(5) Uani d . 1
H H7 0.6321 0.3607 0.4405 0.021 Uiso calc R 1
C C8 0.4368(4) 0.4703(2) 0.49567(11) 0.0156(5) Uani d . 1
N N9 0.3166(4) 0.5927(2) 0.50949(9) 0.0178(5) Uani d . 1
C C10 0.0731(4) 0.5604(3) 0.52208(12) 0.0206(6) Uani d . 1
H H10A 0.0050 0.5212 0.4819 0.025 Uiso calc R 1
H H10B -0.0108 0.6439 0.5324 0.025 Uiso calc R 1
C C11 0.0451(5) 0.4603(2) 0.57997(12) 0.0202(6) Uani d . 1
H H11A -0.0476 0.5014 0.6153 0.024 Uiso calc R 1
H H11B -0.0342 0.3785 0.5646 0.024 Uiso calc R 1
C C12 0.2845(5) 0.4238(2) 0.60652(12) 0.0205(6) Uani d . 1
H H12 0.2740 0.3573 0.6432 0.025 Uiso calc R 1
O O13 0.5189(3) 0.26066(16) 0.55027(8) 0.0217(4) Uani d . 1
C C13 0.4252(4) 0.3700(2) 0.55038(11) 0.0165(5) Uani d . 1
C C14 0.4016(5) 0.5535(2) 0.62937(12) 0.0226(6) Uani d . 1
H H14A 0.5576 0.5336 0.6454 0.027 Uiso calc R 1
H H14B 0.3138 0.5942 0.6659 0.027 Uiso calc R 1
C C15 0.4133(5) 0.6524(2) 0.57049(11) 0.0211(6) Uani d . 1
H H15A 0.3275 0.7348 0.5816 0.025 Uiso calc R 1
H H15B 0.5745 0.6777 0.5626 0.025 Uiso calc R 1
C C16 0.7073(5) 0.7674(3) 0.20801(12) 0.0259(6) Uani d . 1
H H16A 0.7866 0.8494 0.2215 0.039 Uiso calc R 1
H H16B 0.5614 0.7909 0.1873 0.039 Uiso calc R 1
H H16C 0.8022 0.7182 0.1765 0.039 Uiso calc R 1
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 C1 C6 118.4(2) ?
C2 C1 C7 123.5(2) y
C6 C1 C7 118.0(2) ?
C3 C2 C1 120.3(2) ?
C3 C2 H2 119.8 ?
C1 C2 H2 119.8 ?
C2 C3 C4 121.7(2) ?
C2 C3 H3 119.1 ?
C4 C3 H3 119.1 ?
C5 C4 C3 117.6(2) ?
C5 C4 C16 121.7(2) ?
C3 C4 C16 120.8(2) ?
C4 C5 C6 121.8(2) ?
C4 C5 H5 119.1 ?
C6 C5 H5 119.1 ?
C5 C6 C1 120.1(2) ?
C5 C6 H6 120.0 ?
C1 C6 H6 120.0 ?
C8 C7 C1 129.2(2) y
C8 C7 H7 115.4 ?
C1 C7 H7 115.4 ?
C7 C8 N9 125.5(2) y
C7 C8 C13 120.8(2) y
N9 C8 C13 113.62(19) y
C8 N9 C10 108.6(2) y
C8 N9 C15 108.50(19) ?
C10 N9 C15 108.0(2) ?
N9 C10 C11 111.8(2) ?
N9 C10 H10A 109.2 ?
C11 C10 H10A 109.2 ?
N9 C10 H10B 109.2 ?
C11 C10 H10B 109.2 ?
H10A C10 H10B 107.9 ?
C12 C11 C10 108.71(19) ?
C12 C11 H11A 109.9 ?
C10 C11 H11A 109.9 ?
C12 C11 H11B 109.9 ?
C10 C11 H11B 109.9 ?
H11A C11 H11B 108.3 ?
C13 C12 C14 106.6(2) ?
C13 C12 C11 108.4(2) ?
C14 C12 C11 108.1(2) ?
C13 C12 H12 111.2 ?
C14 C12 H12 111.2 ?
C11 C12 H12 111.2 ?
O13 C13 C8 125.1(2) y
O13 C13 C12 124.5(2) y
C8 C13 C12 110.4(2) y
C12 C14 C15 108.80(19) ?
C12 C14 H14A 109.9 ?
C15 C14 H14A 109.9 ?
C12 C14 H14B 109.9 ?
C15 C14 H14B 109.9 ?
H14A C14 H14B 108.3 ?
N9 C15 C14 111.78(19) ?
N9 C15 H15A 109.3 ?
C14 C15 H15A 109.3 ?
N9 C15 H15B 109.3 ?
C14 C15 H15B 109.3 ?
H15A C15 H15B 107.9 ?
C4 C16 H16A 109.5 ?
C4 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C4 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.400(3) ?
C1 C6 1.402(3) ?
C1 C7 1.468(3) y
C2 C3 1.383(3) ?
C2 H2 0.9500 ?
C3 C4 1.397(4) ?
C3 H3 0.9500 ?
C4 C5 1.386(3) ?
C4 C16 1.510(3) y
C5 C6 1.392(3) ?
C5 H5 0.9500 ?
C6 H6 0.9500 ?
C7 C8 1.332(3) y
C7 H7 0.9500 ?
C8 N9 1.438(3) y
C8 C13 1.498(3) y
N9 C10 1.484(3) y
N9 C15 1.488(3) ?
C10 C11 1.553(3) ?
C10 H10A 0.9900 ?
C10 H10B 0.9900 ?
C11 C12 1.545(4) ?
C11 H11A 0.9900 ?
C11 H11B 0.9900 ?
C12 C13 1.507(3) ?
C12 C14 1.537(3) ?
C12 H12 1.0000 ?
O13 C13 1.221(3) y
C14 C15 1.553(3) ?
C14 H14A 0.9900 ?
C14 H14B 0.9900 ?
C15 H15A 0.9900 ?
C15 H15B 0.9900 ?
C16 H16A 0.9800 ?
C16 H16B 0.9800 ?
C16 H16C 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
C6 C1 C2 C3 -0.9(3) ?
C7 C1 C2 C3 -179.4(2) ?
C1 C2 C3 C4 -0.9(4) ?
C2 C3 C4 C5 1.7(4) ?
C2 C3 C4 C16 -177.0(2) ?
C3 C4 C5 C6 -0.6(4) ?
C16 C4 C5 C6 178.1(2) ?
C4 C5 C6 C1 -1.2(4) ?
C2 C1 C6 C5 2.0(3) ?
C7 C1 C6 C5 -179.4(2) ?
C2 C1 C7 C8 -27.5(4) y
C6 C1 C7 C8 154.0(3) ?
C1 C7 C8 N9 -3.1(4) ?
C1 C7 C8 C13 179.0(2) y
C7 C8 N9 C10 122.8(3) ?
C13 C8 N9 C10 -59.2(3) ?
C7 C8 N9 C15 -120.0(3) ?
C13 C8 N9 C15 58.0(2) ?
C8 N9 C10 C11 58.0(3) ?
C15 N9 C10 C11 -59.5(3) ?
N9 C10 C11 C12 -0.5(3) ?
C10 C11 C12 C13 -56.0(2) ?
C10 C11 C12 C14 59.2(3) ?
C7 C8 C13 O13 0.0(4) y
N9 C8 C13 O13 -178.1(2) ?
C7 C8 C13 C12 178.9(2) ?
N9 C8 C13 C12 0.8(3) ?
C14 C12 C13 O13 119.7(2) ?
C11 C12 C13 O13 -124.1(2) ?
C14 C12 C13 C8 -59.3(3) ?
C11 C12 C13 C8 56.9(3) ?
C13 C12 C14 C15 58.5(3) ?
C11 C12 C14 C15 -57.8(3) ?
C8 N9 C15 C14 -56.5(3) ?
C10 N9 C15 C14 61.0(3) ?
C12 C14 C15 N9 -1.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20177254
