#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007329.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_2007329
loop_
_publ_author_name
'Elgemeie, G. E. H.'
'Hanfy, N.'
'Hopf, H.'
'Jones, P. G.'
_publ_section_title
;
 2-Dicyanomethylene-5,6-dimethyl-1,2-dihydropyridine-3-carbonitrile
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              820
_journal_page_last               822
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C11 H8 N4'
_chemical_formula_sum            'C11 H8 N4'
_chemical_formula_weight         196.21
_chemical_name_systematic
;
 2-Dicyanomethylene-5,6-dimethyl-3-cyano-1,2-dihydropyridine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 106.11(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.712(3)
_cell_length_b                   11.579(4)
_cell_length_c                   11.416(4)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      10.0
_cell_volume                     979.4(6)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1992a)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1992b)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      143(2)
_diffrn_measurement_device       'Stoe Stadi-4'
_diffrn_measurement_method       \w/\q
_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  0.024
_diffrn_reflns_av_sigmaI/netI    0.053
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2432
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.26
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.199
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.018
_refine_ls_goodness_of_fit_obs   1.084
_refine_ls_hydrogen_treatment
'H atoms treated by a mixture of independent and constrained refinement'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_restrained_S_obs      1.084
_refine_ls_R_factor_all          0.090
_refine_ls_R_factor_obs          0.054
_refine_ls_shift/esd_max         0.006
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0553P)^2^+0.5865P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.143
_refine_ls_wR_factor_obs         0.123
_reflns_number_observed          1163
_reflns_number_total             1726
_reflns_observed_criterion       I>2\s(I)
_[local]_cod_data_source_file    fg1411.cif
_[local]_cod_data_source_block   eggy
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_database_code               2007329
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0174(11) 0.0362(14) 0.0304(12) 0.0007(10) 0.0086(10) 0.0006(11)
N2 0.0346(13) 0.0579(18) 0.0538(17) -0.0087(13) 0.0229(13) -0.0088(14)
N3 0.0350(14) 0.0614(19) 0.0505(16) -0.0099(14) 0.0199(13) -0.0238(15)
N4 0.0470(16) 0.059(2) 0.0550(17) -0.0192(15) 0.0224(14) -0.0132(16)
C1 0.0187(12) 0.0295(15) 0.0251(13) 0.0015(11) 0.0048(10) 0.0034(12)
C2 0.0219(12) 0.0341(16) 0.0250(13) -0.0007(12) 0.0059(11) 0.0026(12)
C3 0.0220(12) 0.0404(17) 0.0260(14) 0.0016(13) 0.0087(11) 0.0059(13)
C4 0.0273(13) 0.0393(17) 0.0233(13) 0.0043(13) 0.0082(11) 0.0057(13)
C5 0.0272(14) 0.0339(16) 0.0235(13) 0.0020(12) 0.0075(11) 0.0019(12)
C6 0.0226(13) 0.0334(16) 0.0300(14) 0.0020(12) 0.0095(11) -0.0004(13)
C7 0.0276(14) 0.0380(18) 0.0318(15) 0.0012(13) 0.0120(12) -0.0008(13)
C8 0.0242(13) 0.0411(18) 0.0390(16) 0.0009(13) 0.0166(12) -0.0023(15)
C9 0.0259(14) 0.0434(19) 0.0338(15) -0.0011(14) 0.0141(12) 0.0031(15)
C10 0.0398(16) 0.047(2) 0.0352(16) 0.0022(15) 0.0165(14) -0.0011(15)
C11 0.0363(16) 0.0432(19) 0.0362(16) -0.0060(14) 0.0130(13) -0.0071(15)
loop_
_atom_site_label
_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_occupancy
_atom_site_type_symbol
N1 0.7161(3) 0.4441(2) 0.6188(2) 0.0276(6) Uani d . 1 N
H1 0.1820(4) 0.468(3) 0.610(3) 0.038(8) Uiso d . 1 H
N2 1.0035(3) 0.3888(3) 0.4350(2) 0.0466(7) Uani d . 1 N
N3 0.5559(3) 0.1614(3) 0.2947(2) 0.0473(7) Uani d . 1 N
N4 0.2811(4) 0.1438(3) 0.4710(3) 0.0519(8) Uani d . 1 N
C1 0.6292(3) 0.3551(2) 0.5478(2) 0.0247(6) Uani d . 1 C
C2 0.4654(3) 0.3209(2) 0.5712(2) 0.0271(6) Uani d . 1 C
C3 0.4035(3) 0.3793(2) 0.6577(2) 0.0291(7) Uani d . 1 C
H3 0.2915 0.3566 0.6699 0.035 Uiso calc R 1 H
C4 0.4973(3) 0.4693(3) 0.7271(2) 0.0297(7) Uani d . 1 C
C5 0.6610(3) 0.4993(2) 0.7078(2) 0.0281(6) Uani d . 1 C
C6 0.7065(3) 0.3070(2) 0.4610(2) 0.0282(6) Uani d . 1 C
C7 0.8715(4) 0.3506(3) 0.4471(2) 0.0317(7) Uani d . 1 C
C8 0.6196(3) 0.2249(3) 0.3718(3) 0.0332(7) Uani d . 1 C
C9 0.3644(4) 0.2232(3) 0.5120(3) 0.0332(7) Uani d . 1 C
C10 0.4301(4) 0.5282(3) 0.8235(3) 0.0395(8) Uani d . 1 C
H10A 0.5053 0.5056 0.9043 0.047 Uiso calc R 1 H
H10B 0.3048 0.5053 0.8147 0.047 Uiso calc R 1 H
H10C 0.4362 0.6121 0.8141 0.047 Uiso calc R 1 H
C11 0.7844(4) 0.5885(3) 0.7792(3) 0.0380(7) Uani d . 1 C
H11A 0.8921 0.5942 0.7499 0.046 Uiso calc R 1 H
H11B 0.8199 0.5670 0.8656 0.046 Uiso calc R 1 H
H11C 0.7224 0.6633 0.7692 0.046 Uiso calc R 1 H
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'
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
C5 N1 C1 126.3(2) y
N1 C1 C6 118.9(2) ?
N1 C1 C2 114.5(2) y
C6 C1 C2 126.6(2) ?
C3 C2 C1 119.9(2) y
C3 C2 C9 118.2(2) ?
C1 C2 C9 121.9(2) ?
C4 C3 C2 123.1(2) y
C5 C4 C3 116.9(2) y
C5 C4 C10 121.1(3) ?
C3 C4 C10 121.9(2) ?
N1 C5 C4 119.1(3) y
N1 C5 C11 116.8(2) ?
C4 C5 C11 124.1(2) ?
C1 C6 C7 120.5(2) ?
C1 C6 C8 124.3(2) ?
C7 C6 C8 114.7(2) ?
N2 C7 C6 178.2(3) ?
N3 C8 C6 175.4(3) ?
N4 C9 C2 176.0(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C5 1.364(3) y
N1 C1 1.367(3) y
N2 C7 1.154(3) ?
N3 C8 1.147(4) ?
N4 C9 1.144(4) ?
C1 C6 1.405(4) y
C1 C2 1.418(3) y
C2 C3 1.387(4) y
C2 C9 1.432(4) ?
C3 C4 1.385(4) y
C4 C5 1.385(4) y
C4 C10 1.504(4) ?
C5 C11 1.486(4) ?
C6 C7 1.418(4) ?
C6 C8 1.418(4) ?
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
C5 N1 C1 C6 -179.2(3)
C5 N1 C1 C2 0.9(4)
N1 C1 C2 C3 1.9(4)
C6 C1 C2 C3 -178.0(3)
N1 C1 C2 C9 -175.0(2)
C6 C1 C2 C9 5.2(4)
C1 C2 C3 C4 -2.0(4)
C9 C2 C3 C4 174.9(3)
C2 C3 C4 C5 -0.7(4)
C2 C3 C4 C10 -177.8(3)
C1 N1 C5 C4 -3.7(4)
C1 N1 C5 C11 175.8(2)
C3 C4 C5 N1 3.3(4)
C10 C4 C5 N1 -179.5(2)
C3 C4 C5 C11 -176.1(3)
C10 C4 C5 C11 1.0(4)
N1 C1 C6 C7 -0.2(4)
C2 C1 C6 C7 179.6(3)
N1 C1 C6 C8 -171.6(3)
C2 C1 C6 C8 8.2(4)