data_2010725
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  384
_journal_page_last  385
_publ_section_title
;
A new precursor for the synthesis of porphyrazine:
2,3-di-(4-methylphenyl)maleonitrile
;
loop_
_publ_author_name
  'Faulmann, Christophe'
  'Cassoux, Patrick'
  'Pullen, Anthony E.'
_chemical_name_common  bis(4-methylphenyl)maleonitrile
_chemical_formula_moiety  'C18 H14 N2'
_chemical_formula_sum  'C18 H14 N2'
_chemical_formula_weight  258.31
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  8.5424(8)
_cell_length_b  18.089(2)
_cell_length_c  9.3202(9)
_cell_angle_alpha  90.00
_cell_angle_beta  90.898(11)
_cell_angle_gamma  90.00
_cell_volume  1440.0(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  160(2)
_exptl_crystal_density_diffrn  1.192
_diffrn_ambient_temperature  160(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
  C1  .47115(16)  .19171(8)  .24459(17)  .0312(4) Uani d . 1 . . C
  C2  .47219(16)  .11648(8)  .24911(17)  .0300(3) Uani d . 1 . . C
  C3  .59308(19)  .22740(8)  .16402(19)  .0386(4) Uani d . 1 . . C
  C4  .57971(17)  .07937(8)  .15590(18)  .0328(4) Uani d . 1 . . C
  C5  .35478(16)  .24199(8)  .30717(17)  .0307(3) Uani d . 1 . . C
  C6  .39837(17)  .31218(8)  .35387(18)  .0343(4) Uani d . 1 . . C
  H6  .5045  .3273  .3474  .041 Uiso calc R 1 . . H
  C7  .28962(18)  .35972(8)  .40915(18)  .0381(4) Uani d . 1 . . C
  H7  .3221  .4071  .4420  .046 Uiso calc R 1 . . H
  C8  .13319(19)  .33991(8)  .41792(19)  .0394(4) Uani d . 1 . . C
  C9  .08933(19)  .27076(9)  .3675(2)  .0442(4) Uani d . 1 . . C
  H9  -.0175  .2564  .3710  .053 Uiso calc R 1 . . H
  C10  .19770(18)  .22244(8)  .3123(2)  .0397(4) Uani d . 1 . . C
  H10  .1648  .1755  .2777  .048 Uiso calc R 1 . . H
  C11  .0151(2)  .39230(11)  .4794(2)  .0573(5) Uani d . 1 . . C
  H11A  .062(2)  .4431(9)  .487(5)  .069 Uiso calc PR  .50 . . H
  H11B  -.016(4)  .3747(15)  .577(2)  .069 Uiso calc PR  .50 . . H
  H11C  -.080(3)  .394(2)  .415(3)  .069 Uiso calc PR  .50 . . H
  H11D  -.085(2)  .3648(7)  .499(5)  .069 Uiso calc PR  .50 . . H
  H11E  -.007(4)  .4332(15)  .409(2)  .069 Uiso calc PR  .50 . . H
  H11F  .058(2)  .414(2)  .571(3)  .069 Uiso calc PR  .50 . . H
  C12  .37592(15)  .06696(8)  .33801(17)  .0293(3) Uani d . 1 . . C
  C13  .34716(17)  .08246(8)  .48101(18)  .0338(4) Uani d . 1 . . C
  H13  .3850  .1271  .5225  .041 Uiso calc R 1 . . H
  C14  .26364(17)  .03309(8)  .56332(18)  .0359(4) Uani d . 1 . . C
  H14  .2445  .0445  .6610  .043 Uiso calc R 1 . . H
  C15  .20717(16)  -.03286(8)  .50625(18)  .0345(4) Uani d . 1 . . C
  C16  .23710(17)  -.04807(8)  .36377(19)  .0377(4) Uani d . 1 . . C
  H16  .1990  -.0928  .3226  .045 Uiso calc R 1 . . H
  C17  .32123(17)  .00041(8)  .28002(19)  .0349(4) Uani d . 1 . . C
  H17  .3419  -.0116  .1829  .042 Uiso calc R 1 . . H
  C18  .11612(19)  -.08676(10)  .5952(2)  .0450(4) Uani d . 1 . . C
  H18A  .065(4)  -.0596(5)  .677(3)  .054 Uiso calc PR  .50 . . H
  H18B  .1895(11)  -.1256(13)  .636(3)  .054 Uiso calc PR  .50 . . H
  H18C  .033(3)  -.1113(15)  .5332(12)  .054 Uiso calc PR  .50 . . H
  H18D  .127(4)  -.1381(7)  .554(2)  .054 Uiso calc PR  .50 . . H
  H18E  .0020(16)  -.0720(12)  .595(3)  .054 Uiso calc PR  .50 . . H
  H18F  .158(3)  -.0864(15)  .6972(15)  .054 Uiso calc PR  .50 . . H
  N1  .68911(19)  .25669(8)  .1013(2)  .0576(5) Uani d . 1 . . N
  N2  .66194(16)  .04879(7)  .08024(16)  .0411(4) Uani d . 1 . . N
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
  C1  .0305(7)  .0287(8)  .0345(10)  -.0028(6)  .0024(6)  -.0006(7)
  C2  .0295(7)  .0283(8)  .0321(9)  -.0003(6)  .0017(6)  -.0024(6)
  C3  .0409(9)  .0287(8)  .0464(11)  -.0020(7)  .0090(8)  -.0024(7)
  C4  .0343(8)  .0277(8)  .0367(10)  -.0017(6)  .0043(7)  .0012(7)
  C5  .0344(8)  .0255(7)  .0324(9)  .0003(6)  .0021(6)  .0002(6)
  C6  .0375(8)  .0267(8)  .0387(10)  -.0032(6)  -.0013(7)  .0003(7)
  C7  .0505(9)  .0244(8)  .0393(11)  .0015(7)  -.0020(7)  -.0023(7)
  C8  .0495(9)  .0327(9)  .0360(10)  .0111(7)  .0041(7)  .0016(7)
  C9  .0338(8)  .0365(9)  .0623(13)  .0034(7)  .0059(8)  .0001(8)
  C10  .0370(8)  .0276(8)  .0545(12)  -.0016(6)  .0040(7)  -.0051(7)
  C11  .0629(12)  .0476(11)  .0616(14)  .0204(9)  .0071(10)  -.0054(10)
  C12  .0301(7)  .0244(7)  .0334(10)  .0017(6)  .0013(6)  -.0001(6)
  C13  .0383(8)  .0289(8)  .0341(10)  -.0007(6)  .0003(7)  -.0028(7)
  C14  .0405(8)  .0373(9)  .0300(10)  .0039(7)  .0033(7)  -.0001(7)
  C15  .0307(7)  .0348(8)  .0380(11)  .0013(6)  .0006(6)  .0066(7)
  C16  .0405(9)  .0303(8)  .0424(11)  -.0051(6)  .0011(7)  -.0008(7)
  C17  .0418(8)  .0298(8)  .0331(10)  -.0009(6)  .0051(7)  -.0051(7)
  C18  .0409(9)  .0462(10)  .0480(12)  -.0051(7)  .0028(8)  .0115(8)
  N1  .0565(9)  .0416(8)  .0753(13)  -.0106(7)  .0237(9)  -.0012(8)
  N2  .0447(7)  .0342(7)  .0448(10)  -.0006(6)  .0106(7)  -.0025(6)
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 C2 . 1.362(2) yes
  C1 C3 . 1.446(2) yes
  C1 C5 . 1.474(2) yes
  C2 C4 . 1.440(2) yes
  C2 C12 . 1.479(2) yes
  C3 N1 . 1.145(2) yes
  C4 N2 . 1.146(2) yes
  C5 C10 . 1.389(2) ?
  C5 C6 . 1.391(2) ?
  C6 C7 . 1.372(2) ?
  C7 C8 . 1.387(2) ?
  C8 C9 . 1.386(2) ?
  C8 C11 . 1.504(2) yes
  C9 C10 . 1.378(2) ?
  C12 C13 . 1.388(2) ?
  C12 C17 . 1.397(2) ?
  C13 C14 . 1.383(2) ?
  C14 C15 . 1.389(2) ?
  C15 C16 . 1.384(2) ?
  C15 C18 . 1.505(2) yes
  C16 C17 . 1.383(2) ?