#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/32/2003297.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_2003297
loop_
_publ_author_name
'Schollmeyer, D.'
'Keilhofer, D.'
'Pindur, U.'
_publ_section_title
;
 Diels--Alder Products of the Alkaloid ({-})-Thebaine with
 \a-Chloroacrylnitrile and 1-Methoxy-1,3-cyclohexadiene with
 Tetracyanoethene
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              502
_journal_page_last               505
_journal_paper_doi               10.1107/S0108270194007900
_journal_volume                  51
_journal_year                    1995
_chemical_compound_source
;
slow evaporation of chloroform solution of (2)
;
_chemical_formula_sum            'C13 H10 N4 O'
_chemical_formula_weight         238.25
_chemical_name_systematic
;
1-Methoxy-5,5,6,6-tetracyanobicyclo[2.2.2]oct-3-ene
;
_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'
_audit_creation_method           SHELXL93
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5252(5)
_cell_length_b                   9.398(1)
_cell_length_c                   17.2900(7)
_cell_measurement_reflns_used    74
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70
_cell_measurement_theta_min      65
_cell_volume                     1222.78(16)
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2648
_diffrn_reflns_theta_max         69.90
_diffrn_reflns_theta_min         5.12
_diffrn_standards_decay_%        5
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Reddish
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             496
_exptl_crystal_size_max          1.09
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.168
_refine_ls_abs_structure_details '\c = 0.4(4) (Flack, 1983)'
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_extinction_coef       0.0038(14)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.027
_refine_ls_goodness_of_fit_obs   1.031
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_restrained_S_obs      1.031
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_obs          0.0527
_refine_ls_shift/esd_max         -0.003
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo^2^)+(0.1125P)^2^+0.1044P]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1421
_refine_ls_wR_factor_obs         0.1407
_reflns_number_observed          2218
_reflns_number_total             2277
_reflns_observed_criterion       >2\s(I)
_cod_data_source_file            se1061.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.1125P)^2^+0.1044P]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1/[\s^2^(Fo^2^)+(0.1125P)^2^+0.1044P]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1222.8(2)
_cod_database_code               2003297
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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_22
_atom_site_aniso_U_23
_atom_site_aniso_U_33
C1 0.0514(11) -0.0021(8) 0.0020(8) 0.0483(9) -0.0035(7) 0.0424(9)
C2 0.0528(11) -0.0027(9) -0.0009(8) 0.0653(12) -0.0121(8) 0.0408(9)
C3 0.0527(12) 0.0056(10) 0.0064(8) 0.0848(15) -0.0060(9) 0.0369(8)
C4 0.0347(9) -0.0009(9) 0.0054(7) 0.0760(13) -0.0018(9) 0.0473(9)
C5 0.0386(8) -0.0051(7) -0.0013(7) 0.0541(9) 0.0032(7) 0.0365(8)
C6 0.0368(8) -0.0013(7) 0.0002(6) 0.0482(8) 0.0014(6) 0.0324(7)
C7 0.0507(12) 0.0147(11) -0.0046(9) 0.086(2) -0.0087(11) 0.0572(12)
C8 0.071(2) 0.0208(11) -0.0031(10) 0.0674(13) -0.0024(10) 0.0540(11)
C9 0.0474(10) -0.0012(8) 0.0031(7) 0.0528(9) 0.0015(7) 0.0385(9)
N1 0.0776(13) -0.0068(11) 0.0057(7) 0.0836(13) 0.0046(8) 0.0378(8)
C10 0.0393(10) -0.0016(8) 0.0000(7) 0.0581(10) 0.0025(8) 0.0433(8)
N2 0.0435(10) 0.0008(9) -0.0088(9) 0.0868(14) 0.0139(10) 0.0733(12)
C11 0.0525(10) -0.0084(8) -0.0031(8) 0.0593(10) -0.0002(8) 0.0460(9)
N3 0.0691(12) -0.0126(11) -0.0191(9) 0.0814(13) -0.0093(10) 0.0603(11)
C12 0.0457(10) -0.0038(9) 0.0034(8) 0.0643(11) 0.0108(9) 0.0484(10)
N4 0.0765(14) 0.0015(11) 0.0106(11) 0.0761(13) 0.0306(11) 0.0759(14)
O1 0.0723(11) -0.0193(7) 0.0148(7) 0.0560(8) -0.0072(7) 0.0638(9)
C13 0.131(3) -0.034(2) 0.023(2) 0.0607(14) -0.0178(15) 0.095(2)
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
C1 1 0.1974(3) 0.3606(2) 0.87082(10) 0.0474(4) Uani d . C
C2 1 0.2124(3) 0.3842(2) 0.78435(11) 0.0530(5) Uani d . C
H2 1 0.1572(3) 0.3300(2) 0.76013(11) 0.088(11) Uiso d R H
C3 1 0.3525(3) 0.4664(3) 0.76335(11) 0.0581(6) Uani d . C
H3 1 0.3816(3) 0.4963(3) 0.72023(11) 0.060(7) Uiso d R H
C4 1 0.4660(3) 0.5150(3) 0.83029(11) 0.0526(5) Uani d . C
H4 1 0.5616(3) 0.5751(3) 0.81996(11) 0.077(9) Uiso d R H
C5 1 0.3425(2) 0.6074(2) 0.88505(10) 0.0431(4) Uani d . C
C6 1 0.1732(2) 0.5136(2) 0.90747(9) 0.0391(4) Uani d . C
C7 1 0.5264(3) 0.3858(3) 0.87587(14) 0.0645(6) Uani d . C
H7A 1 0.5868(3) 0.3345(3) 0.84009(14) 0.100(9) Uiso d R H
H7B 1 0.5855(3) 0.4194(3) 0.91965(14) 0.100(9) Uiso d R H
C8 1 0.3714(4) 0.2977(3) 0.90137(13) 0.0641(6) Uani d . C
H8A 1 0.3625(4) 0.2973(3) 0.96026(13) 0.111(9) Uiso d R H
H8B 1 0.3695(4) 0.2026(3) 0.88026(13) 0.111(9) Uiso d R H
C9 1 0.1501(2) 0.4995(2) 0.99205(10) 0.0462(4) Uani d . C
N1 1 0.1305(3) 0.4860(2) 1.05666(9) 0.0663(5) Uani d . N
C10 1 0.0086(2) 0.5750(2) 0.87629(11) 0.0469(4) Uani d . C
N2 1 -0.1193(3) 0.6204(3) 0.84990(13) 0.0679(6) Uani d . N
C11 1 0.4473(3) 0.6496(2) 0.95378(11) 0.0526(5) Uani d . C
N3 1 0.5372(3) 0.6799(2) 1.00374(12) 0.0703(6) Uani d . N
C12 1 0.2915(3) 0.7386(2) 0.84392(11) 0.0528(5) Uani d . C
N4 1 0.2583(3) 0.8366(3) 0.80851(13) 0.0762(7) Uani d . N
O1 1 0.0429(3) 0.2866(2) 0.89409(10) 0.0640(5) Uani d . O
C13 1 0.0279(6) 0.1443(3) 0.8664(2) 0.0957(12) Uani d . C
H13A 1 -0.0889(17) 0.1085(14) 0.8776(20) 0.154(12) Uiso calc R H
H13B 1 0.1150(33) 0.0856(9) 0.8914(16) 0.154(12) Uiso calc R H
H13C 1 0.0473(51) 0.1428(7) 0.8115(4) 0.154(12) Uiso calc R H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0181 0.009
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000
N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0311 0.018
O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0492 0.032
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
6 2 0
0 4 12
-6 -2 0
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
O1 C1 C2 114.5(2) yes
O1 C1 C8 114.5(2) yes
C2 C1 C8 109.5(2) yes
O1 C1 C6 103.79(14) yes
C2 C1 C6 105.7(2) yes
C8 C1 C6 108.2(2) yes
C3 C2 C1 113.9(2) yes
C2 C3 C4 114.0(2) yes
C3 C4 C7 109.0(2) yes
C3 C4 C5 107.0(2) yes
C7 C4 C5 107.7(2) yes
C12 C5 C11 107.6(2) yes
C12 C5 C4 108.8(2) yes
C11 C5 C4 108.3(2) yes
C12 C5 C6 111.77(15) yes
C11 C5 C6 112.22(14) yes
C4 C5 C6 108.09(15) yes
C10 C6 C9 107.42(15) yes
C10 C6 C1 107.89(15) yes
C9 C6 C1 109.16(15) yes
C10 C6 C5 111.53(15) yes
C9 C6 C5 112.52(14) yes
C1 C6 C5 108.20(14) yes
C8 C7 C4 111.2(2) yes
C7 C8 C1 110.6(2) yes
N1 C9 C6 178.5(2) yes
N2 C10 C6 177.9(2) yes
N3 C11 C5 175.6(3) yes
N4 C12 C5 175.7(2) yes
C1 O1 C13 115.6(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.414(3) yes
C1 C2 1.516(3) yes
C1 C8 1.531(3) yes
C1 C6 1.582(3) yes
C2 C3 1.356(3) yes
C3 C4 1.509(3) yes
C4 C7 1.518(3) yes
C4 C5 1.585(3) yes
C5 C12 1.475(3) yes
C5 C11 1.481(3) yes
C5 C6 1.597(2) yes
C6 C10 1.468(3) yes
C6 C9 1.479(2) yes
C7 C8 1.497(4) yes
C9 N1 1.134(2) yes
C10 N2 1.148(3) yes
C11 N3 1.133(3) yes
C12 N4 1.133(3) yes
O1 C13 1.425(3) yes
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
C1 C2 C3 C4 1.0(2) yes
C4 C7 C8 C1 2.5(2) yes
C4 C5 C6 C1 3.3(2) yes
C2 C1 C6 C5 -59.5(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21187413
2 PubChem 139054197