#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/30/2223022.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_2223022
loop_
_publ_author_name
'Büyükgüngör, Orhan'
'Yavuz, Serkan'
'Odabaşoğlu, Mustafa'
'Pamir, Özgür'
'Yıldırır, Yılmaz'
_publ_section_title
;
 1-Methoxy-3-o-tolylbicyclo[2.2.2]oct-5-ene-2,2-dicarbonitrile
;
_journal_coeditor_code           CI2877
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2208
_journal_paper_doi               10.1107/S1600536809032474
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H18 N2 O'
_chemical_formula_moiety         'C18 H18 N2 O'
_chemical_formula_sum            'C18 H18 N2 O'
_chemical_formula_weight         278.34
_chemical_name_systematic
;
1-Methoxy-3-o-tolylbicyclo[2.2.2]oct-5-ene-2,2-dicarbonitrile
;
_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                91.201(7)
_cell_angle_beta                 107.206(6)
_cell_angle_gamma                110.856(6)
_cell_formula_units_Z            2
_cell_length_a                   7.5922(6)
_cell_length_b                   9.5026(8)
_cell_length_c                   11.5584(9)
_cell_measurement_reflns_used    8047
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.13
_cell_measurement_theta_min      1.86
_cell_volume                     736.89(11)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       'ω-scan rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8047
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        -2.6
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_correction_T_min  0.9561
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0409
_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)+(0.0455P)²+0.127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                2532
_reflns_number_total             3057
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2877.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_original_cell_volume        736.89(10)
_cod_database_code               2223022
_cod_database_fobs_code          2223022
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.76186(18) 0.53676(14) 0.34535(12) 0.0411(3) Uani d . 1 . .
C C2 0.75171(19) 0.51461(15) 0.46312(12) 0.0434(3) Uani d . 1 . .
C C3 0.6500(2) 0.36832(17) 0.48325(14) 0.0522(4) Uani d . 1 . .
H H3 0.6401 0.3530 0.5607 0.063 Uiso calc R 1 . .
C C4 0.5636(2) 0.24556(17) 0.39194(16) 0.0584(4) Uani d . 1 . .
H H4 0.4979 0.1488 0.4081 0.070 Uiso calc R 1 . .
C C5 0.5753(2) 0.26716(17) 0.27703(16) 0.0594(4) Uani d . 1 . .
H H5 0.5185 0.1848 0.2151 0.071 Uiso calc R 1 . .
C C6 0.6717(2) 0.41157(16) 0.25353(14) 0.0526(4) Uani d . 1 . .
H H6 0.6766 0.4256 0.1750 0.063 Uiso calc R 1 . .
C C7 0.8491(2) 0.64107(17) 0.56952(13) 0.0522(3) Uani d . 1 . .
H H7A 0.8152 0.6031 0.6396 0.078 Uiso calc R 1 . .
H H7B 0.8031 0.7220 0.5486 0.078 Uiso calc R 1 . .
H H7C 0.9911 0.6787 0.5882 0.078 Uiso calc R 1 . .
C C8 0.87437(18) 0.69280(14) 0.31871(11) 0.0390(3) Uani d . 1 . .
H H8 0.9680 0.7512 0.3977 0.047 Uiso calc R 1 . .
C C9 0.74043(18) 0.78601(14) 0.26415(11) 0.0398(3) Uani d . 1 . .
C C10 0.8251(2) 0.88159(16) 0.16893(12) 0.0454(3) Uani d . 1 . .
C C11 0.7944(2) 0.76528(19) 0.06747(13) 0.0543(4) Uani d . 1 . .
H H11 0.7201 0.7619 -0.0133 0.065 Uiso calc R 1 . .
C C12 0.8816(2) 0.66815(18) 0.10214(13) 0.0528(4) Uani d . 1 . .
H H12 0.8691 0.5884 0.0483 0.063 Uiso calc R 1 . .
C C13 1.00195(19) 0.69628(15) 0.23466(12) 0.0440(3) Uani d . 1 . .
H H13 1.0670 0.6232 0.2537 0.053 Uiso calc R 1 . .
C C14 0.5290(2) 0.68754(16) 0.20146(13) 0.0473(3) Uani d . 1 . .
C C15 0.7433(2) 0.88992(15) 0.36219(12) 0.0438(3) Uani d . 1 . .
C C16 1.0492(2) 0.97044(16) 0.23344(14) 0.0487(3) Uani d . 1 . .
H H16A 1.1033 1.0413 0.1820 0.058 Uiso calc R 1 . .
H H16B 1.0693 1.0283 0.3096 0.058 Uiso calc R 1 . .
C C17 1.1581(2) 0.86011(16) 0.25968(13) 0.0475(3) Uani d . 1 . .
H H17A 1.2439 0.8831 0.3443 0.057 Uiso calc R 1 . .
H H17B 1.2402 0.8707 0.2076 0.057 Uiso calc R 1 . .
C C18 0.7764(3) 1.0878(2) 0.0652(2) 0.0806(6) Uani d . 1 . .
H H18A 0.8949 1.1689 0.1157 0.121 Uiso calc R 1 . .
H H18B 0.6739 1.1264 0.0319 0.121 Uiso calc R 1 . .
H H18C 0.8045 1.0458 -0.0004 0.121 Uiso calc R 1 . .
N N1 0.3655(2) 0.61425(17) 0.15462(14) 0.0698(4) Uani d . 1 . .
N N2 0.7485(2) 0.96949(16) 0.43909(13) 0.0622(4) Uani d . 1 . .
O O1 0.71183(17) 0.97361(13) 0.13594(10) 0.0617(3) Uani d . 1 . .
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'
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
C6 C1 C2 . . 118.87(12) ?
C6 C1 C8 . . 120.32(12) ?
C2 C1 C8 . . 120.77(11) ?
C3 C2 C1 . . 118.44(13) ?
C3 C2 C7 . . 118.43(13) ?
C1 C2 C7 . . 123.11(12) ?
C4 C3 C2 . . 121.98(14) ?
C4 C3 H3 . . 119.0 ?
C2 C3 H3 . . 119.0 ?
C5 C4 C3 . . 119.50(14) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
C4 C5 C6 . . 119.87(14) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C5 C6 C1 . . 121.31(15) ?
C5 C6 H6 . . 119.3 ?
C1 C6 H6 . . 119.3 ?
C2 C7 H7A . . 109.5 ?
C2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C1 C8 C13 . . 115.60(10) ?
C1 C8 C9 . . 114.62(10) ?
C13 C8 C9 . . 107.25(10) ?
C1 C8 H8 . . 106.2 ?
C13 C8 H8 . . 106.2 ?
C9 C8 H8 . . 106.2 ?
C15 C9 C14 . . 106.69(11) ?
C15 C9 C10 . . 109.45(11) ?
C14 C9 C10 . . 108.55(11) ?
C15 C9 C8 . . 110.69(10) ?
C14 C9 C8 . . 112.91(11) ?
C10 C9 C8 . . 108.49(10) ?
O1 C10 C11 . . 114.96(12) ?
O1 C10 C16 . . 114.58(12) ?
C11 C10 C16 . . 109.89(12) ?
O1 C10 C9 . . 104.47(10) ?
C11 C10 C9 . . 104.90(11) ?
C16 C10 C9 . . 107.10(11) ?
C12 C11 C10 . . 114.56(12) ?
C12 C11 H11 . . 122.7 ?
C10 C11 H11 . . 122.7 ?
C11 C12 C13 . . 114.81(13) ?
C11 C12 H12 . . 122.6 ?
C13 C12 H12 . . 122.6 ?
C12 C13 C17 . . 106.54(12) ?
C12 C13 C8 . . 111.97(11) ?
C17 C13 C8 . . 105.91(10) ?
C12 C13 H13 . . 110.7 ?
C17 C13 H13 . . 110.7 ?
C8 C13 H13 . . 110.7 ?
N1 C14 C9 . . 178.43(15) ?
N2 C15 C9 . . 178.70(15) ?
C17 C16 C10 . . 110.08(11) ?
C17 C16 H16A . . 109.6 ?
C10 C16 H16A . . 109.6 ?
C17 C16 H16B . . 109.6 ?
C10 C16 H16B . . 109.6 ?
H16A C16 H16B . . 108.2 ?
C16 C17 C13 . . 108.74(11) ?
C16 C17 H17A . . 109.9 ?
C13 C17 H17A . . 109.9 ?
C16 C17 H17B . . 109.9 ?
C13 C17 H17B . . 109.9 ?
H17A C17 H17B . . 108.3 ?
O1 C18 H18A . . 109.5 ?
O1 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O1 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C18 O1 C10 . . 116.48(12) ?
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
C1 C6 . 1.3955(19) ?
C1 C2 . 1.4019(19) ?
C1 C8 . 1.5153(17) ?
C2 C3 . 1.3923(19) ?
C2 C7 . 1.5068(19) ?
C3 C4 . 1.378(2) ?
C3 H3 . 0.93 ?
C4 C5 . 1.372(2) ?
C4 H4 . 0.93 ?
C5 C6 . 1.382(2) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
C8 C13 . 1.5551(18) ?
C8 C9 . 1.5816(17) ?
C8 H8 . 0.98 ?
C9 C15 . 1.4776(18) ?
C9 C14 . 1.4804(18) ?
C9 C10 . 1.5794(18) ?
C10 O1 . 1.4160(17) ?
C10 C11 . 1.501(2) ?
C10 C16 . 1.5372(19) ?
C11 C12 . 1.321(2) ?
C11 H11 . 0.93 ?
C12 C13 . 1.494(2) ?
C12 H12 . 0.93 ?
C13 C17 . 1.5417(19) ?
C13 H13 . 0.98 ?
C14 N1 . 1.1355(19) ?
C15 N2 . 1.1371(18) ?
C16 C17 . 1.535(2) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C18 O1 . 1.408(2) ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
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
C12 H12 N1 2_665 0.93 2.70 3.509(3) 146
C7 H7C Cg1 2_766 0.96 2.84 3.688(2) 146
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.63(19) ?
C8 C1 C2 C3 . . . . -178.64(12) ?
C6 C1 C2 C7 . . . . 178.11(13) ?
C8 C1 C2 C7 . . . . 0.10(19) ?
C1 C2 C3 C4 . . . . 1.4(2) ?
C7 C2 C3 C4 . . . . -177.44(13) ?
C2 C3 C4 C5 . . . . -0.8(2) ?
C3 C4 C5 C6 . . . . -0.6(2) ?
C4 C5 C6 C1 . . . . 1.3(2) ?
C2 C1 C6 C5 . . . . -0.7(2) ?
C8 C1 C6 C5 . . . . 177.32(13) ?
C6 C1 C8 C13 . . . . -39.45(17) ?
C2 C1 C8 C13 . . . . 138.53(12) ?
C6 C1 C8 C9 . . . . 86.10(15) ?
C2 C1 C8 C9 . . . . -95.92(14) ?
C1 C8 C9 C15 . . . . 95.40(13) ?
C13 C8 C9 C15 . . . . -134.81(11) ?
C1 C8 C9 C14 . . . . -24.13(15) ?
C13 C8 C9 C14 . . . . 105.66(12) ?
C1 C8 C9 C10 . . . . -144.50(11) ?
C13 C8 C9 C10 . . . . -14.70(13) ?
C15 C9 C10 O1 . . . . -52.60(13) ?
C14 C9 C10 O1 . . . . 63.49(13) ?
C8 C9 C10 O1 . . . . -173.47(10) ?
C15 C9 C10 C11 . . . . -173.91(11) ?
C14 C9 C10 C11 . . . . -57.83(14) ?
C8 C9 C10 C11 . . . . 65.22(13) ?
C15 C9 C10 C16 . . . . 69.33(14) ?
C14 C9 C10 C16 . . . . -174.58(11) ?
C8 C9 C10 C16 . . . . -51.54(13) ?
O1 C10 C11 C12 . . . . -172.24(12) ?
C16 C10 C11 C12 . . . . 56.73(16) ?
C9 C10 C11 C12 . . . . -58.09(15) ?
C10 C11 C12 C13 . . . . -2.60(18) ?
C11 C12 C13 C17 . . . . -57.14(16) ?
C11 C12 C13 C8 . . . . 58.22(17) ?
C1 C8 C13 C12 . . . . 85.22(14) ?
C9 C8 C13 C12 . . . . -44.02(14) ?
C1 C8 C13 C17 . . . . -159.04(11) ?
C9 C8 C13 C17 . . . . 71.72(12) ?
O1 C10 C16 C17 . . . . -177.48(11) ?
C11 C10 C16 C17 . . . . -46.25(15) ?
C9 C10 C16 C17 . . . . 67.16(14) ?
C10 C16 C17 C13 . . . . -10.53(15) ?
C12 C13 C17 C16 . . . . 61.71(14) ?
C8 C13 C17 C16 . . . . -57.67(14) ?
C11 C10 O1 C18 . . . . -74.84(18) ?
C16 C10 O1 C18 . . . . 53.89(18) ?
C9 C10 O1 C18 . . . . 170.76(14) ?
