#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/01/2200131.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_2200131
loop_
_publ_author_name
'Crean, Colm'
'Gallagher, John F.'
'Pratt, Albert C.'
_publ_section_title
;2,2'-{2-[(E)-3-Phenylprop-2-enyl]-2,3-dihydro-1H-isoindol-1,3-diylidene}dimalononitrile,
 a π-deficient system for π···π (1:1) stacking
 investigations
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o236
_journal_page_last               o238
_journal_paper_doi               10.1107/S1600536801002598
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C23 H13 N5'
_chemical_formula_moiety         'C23 H13 N5'
_chemical_formula_structural     'C23 H13 N5'
_chemical_formula_sum            'C23 H13 N5'
_chemical_formula_weight         359.38
_chemical_melting_point          470
_chemical_name_common
2,2'-(Cinnamylisoindolin-1,3-diylidene)bispropanedinitrile
_chemical_name_systematic
;
2,2'-{2-[(E)-3-phenylprop-2-enyl]-2,3-dihydro-1H-isoindol-1,3-diylidene}-
dimalononitrile
;
_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'
_cell_angle_alpha                90
_cell_angle_beta                 108.327(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3872(18)
_cell_length_b                   8.2696(10)
_cell_length_c                   16.1442(15)
_cell_measurement_reflns_used    33
_cell_measurement_temperature    296.0(10)
_cell_measurement_theta_max      20.5
_cell_measurement_theta_min      7.1
_cell_volume                     1823.4(4)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Bruker, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 1998)'
_computing_publication_material
'NRCVAX96, SHELXL97 and WordPerfect macro PREP8 (Ferguson, 1998)'
_computing_structure_refinement
'NRCVAX96 (Gabe et al., 1989) and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296.0(10)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device       'Bruker P4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .012
_diffrn_reflns_av_sigmaI/netI    .024
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4331
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         2.7
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 197
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          .43
_exptl_crystal_size_mid          .38
_exptl_crystal_size_min          .28
_refine_diff_density_max         .25
_refine_diff_density_min         -.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          .059
_refine_ls_R_factor_gt           .042
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0529P)²+0.3178P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .112
_reflns_number_gt                2630
_reflns_number_total             3367
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf6047.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2200131
_cod_database_fobs_code          2200131
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_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
N1 -.00647(8) .87131(15) .15563(8) .0367(3) Uani d . 1 . . N
N2A -.11664(14) 1.4060(2) .04262(12) .0788(6) Uani d . 1 . . N
N3A -.24231(13) 1.0780(3) .17486(15) .0907(6) Uani d . 1 . . N
N2B .28853(13) .5619(2) .18438(12) .0732(5) Uani d . 1 . . N
N3B .04444(12) .42660(19) .24932(11) .0620(4) Uani d . 1 . . N
C1 -.07949(11) .7765(2) .18104(10) .0437(4) Uani d . 1 . . C
C2 -.05987(12) .7661(2) .27751(11) .0470(4) Uani d . 1 . . C
C3 .00903(12) .8440(2) .33779(11) .0458(4) Uani d . 1 . . C
C4 -.01804(11) 1.02862(18) .12450(9) .0380(3) Uani d . 1 . . C
C5 .08302(10) .80880(18) .15561(9) .0349(3) Uani d . 1 . . C
C11 .06880(11) 1.06855(18) .10020(9) .0380(3) Uani d . 1 . . C
C12 .09685(13) 1.2087(2) .06691(10) .0479(4) Uani d . 1 . . C
C13 .18639(13) 1.2119(2) .05246(11) .0539(5) Uani d . 1 . . C
C14 .24716(13) 1.0783(2) .07089(11) .0524(4) Uani d . 1 . . C
C15 .22077(11) .9379(2) .10446(10) .0443(4) Uani d . 1 . . C
C16 .13076(10) .93386(18) .11947(9) .0363(3) Uani d . 1 . . C
C6A -.09671(11) 1.1275(2) .11819(10) .0465(4) Uani d . 1 . . C
C7A -.10479(13) 1.2830(2) .07685(12) .0559(5) Uani d . 1 . . C
C8A -.17655(13) 1.0939(2) .14997(13) .0598(5) Uani d . 1 . . C
C6B .11864(11) .65823(18) .18467(9) .0390(4) Uani d . 1 . . C
C7B .21323(13) .6091(2) .18276(11) .0483(4) Uani d . 1 . . C
C8B .07334(12) .5348(2) .22056(10) .0441(4) Uani d . 1 . . C
C21 .03457(13) .8243(2) .43290(11) .0488(4) Uani d . 1 . . C
C22 -.01487(18) .7189(2) .47126(13) .0697(6) Uani d . 1 . . C
C23 .0135(2) .6989(3) .56013(15) .0909(8) Uani d . 1 . . C
C24 .0913(2) .7812(3) .61307(15) .0896(8) Uani d . 1 . . C
C25 .14131(17) .8881(3) .57716(14) .0791(7) Uani d . 1 . . C
C26 .11258(13) .9101(3) .48711(12) .0601(5) Uani d . 1 . . C
H1A -.0814 .6679 .1578 .052 Uiso calc R 1 . . H
H1B -.1435 .8246 .1547 .052 Uiso calc R 1 . . H
H2 -.1002 .6980 .2969 .056 Uiso calc R 1 . . H
H3 .0453 .9194 .3181 .055 Uiso calc R 1 . . H
H12 .0560 1.2987 .0546 .057 Uiso calc R 1 . . H
H13 .2060 1.3048 .0301 .065 Uiso calc R 1 . . H
H14 .3071 1.0829 .0605 .063 Uiso calc R 1 . . H
H15 .2621 .8486 .1167 .053 Uiso calc R 1 . . H
H22 -.0681 .6608 .4362 .084 Uiso calc R 1 . . H
H23 -.0210 .6282 .5844 .109 Uiso calc R 1 . . H
H24 .1107 .7655 .6731 .108 Uiso calc R 1 . . H
H25 .1943 .9455 .6131 .095 Uiso calc R 1 . . H
H26 .1462 .9831 .4632 .072 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 .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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 1 1
0 1 -5
4 2 -2
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
C1 N1 C4 125.99(12) yes
C1 N1 C5 123.11(12) yes
C4 N1 C5 110.82(12) yes
N1 C1 C2 113.84(13) yes
C1 C2 C3 126.34(15) yes
C2 C3 C21 126.82(16) yes
N1 C4 C6A 126.02(15) yes
N1 C5 C6B 125.80(14) yes
N1 C4 C11 107.12(12) yes
C6A C4 C11 126.86(15) no
C6B C5 C16 127.39(13) no
N1 C5 C16 106.81(12) yes
C4 C11 C12 132.04(14) no
C4 C11 C16 107.42(13) no
C12 C11 C16 120.50(14) no
C11 C12 C13 118.79(16) no
C12 C13 C14 120.64(16) no
C13 C14 C15 121.46(16) no
C14 C15 C16 118.26(16) no
C11 C16 C15 120.35(14) no
C5 C16 C11 107.80(13) no
C5 C16 C15 131.85(14) no
C4 C6A C7A 120.78(16) no
C4 C6A C8A 126.56(16) no
C8A C6A C7A 112.66(15) no
N2A C7A C6A 176.3(2) yes
N3A C8A C6A 175.3(2) yes
C5 C6B C7B 120.42(14) no
C5 C6B C8B 128.19(14) no
C8B C6B C7B 111.37(14) no
N2B C7B C6B 175.81(18) yes
N3B C8B C6B 173.41(18) yes
C3 C21 C22 122.70(17) no
C3 C21 C26 119.39(17) no
C22 C21 C26 117.89(18) no
C21 C22 C23 121.1(2) no
C22 C23 C24 120.8(2) no
C23 C24 C25 119.5(2) no
C24 C25 C26 120.0(2) no
C21 C26 C25 120.6(2) no
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
N1 C1 . 1.469(2) yes
N1 C4 . 1.386(2) yes
N1 C5 . 1.388(2) yes
N2A C7A . 1.145(2) yes
N3A C8A . 1.146(2) yes
N2B C7B . 1.144(2) yes
N3B C8B . 1.145(2) yes
C1 C2 . 1.495(2) yes
C2 C3 . 1.319(2) yes
C3 C21 . 1.471(2) yes
C4 C6A . 1.374(2) yes
C4 C11 . 1.460(2) yes
C5 C6B . 1.372(2) yes
C5 C16 . 1.461(2) yes
C11 C12 . 1.389(2) no
C11 C16 . 1.399(2) no
C12 C13 . 1.380(2) no
C13 C14 . 1.382(3) no
C14 C15 . 1.384(2) no
C15 C16 . 1.391(2) no
C6A C8A . 1.425(3) no
C6A C7A . 1.436(3) no
C6B C8B . 1.428(2) no
C6B C7B . 1.430(2) no
C21 C26 . 1.382(3) no
C21 C22 . 1.388(3) no
C22 C23 . 1.373(3) no
C23 C24 . 1.359(4) no
C24 C25 . 1.377(4) no
C25 C26 . 1.393(3) no
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
_geom_hbond_publ_flag
C1 H1B N3A 1_555 .97 2.61 3.401(2) 139 yes
C12 H12 N2A 1_555 .93 2.59 3.390(3) 145 yes
C12 H12 C7A 1_555 .93 2.45 3.019(3) 119 yes
C15 H15 N2B 1_555 .93 2.59 3.390(2) 145 yes
C15 H15 C7B 1_555 .93 2.46 3.015(2) 119 yes
C14 H14 Cg1 2_555 .93 3.20 3.984(2) 143 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
C4 N1 C1 C2 -102.16(17) yes
C5 N1 C1 C2 81.50(18) yes
N1 C1 C2 C3 6.6(2) yes
C1 C2 C3 C21 -174.28(16) yes
C1 N1 C4 C6A 5.3(2) no
C5 N1 C4 C6A -178.02(14) no
C1 N1 C4 C11 -174.88(13) no
C5 N1 C4 C11 1.84(15) no
C1 N1 C5 C6B -5.2(2) no
C4 N1 C5 C6B 178.01(13) no
C1 N1 C5 C16 175.11(12) no
C4 N1 C5 C16 -1.72(15) no
N1 C4 C11 C12 -178.93(15) no
N1 C4 C11 C16 -1.22(15) no
C6A C4 C11 C12 .9(3) no
C6A C4 C11 C16 178.64(14) no
C4 C11 C12 C13 178.09(15) no
C16 C11 C12 C13 .6(2) no
C12 C11 C16 C5 178.22(13) no
C12 C11 C16 C15 -.8(2) no
C11 C12 C13 C14 -.1(2) no
C12 C13 C14 C15 -.2(3) no
C13 C14 C15 C16 .0(2) no
C14 C15 C16 C11 .5(2) no
C14 C15 C16 C5 -178.28(15) no
C4 C11 C16 C5 .19(15) no
C4 C11 C16 C15 -178.86(13) no
C6B C5 C16 C11 -178.82(14) no
C6B C5 C16 C15 .1(3) no
N1 C5 C16 C11 .90(15) no
N1 C5 C16 C15 179.80(15) no
N1 C4 C6A C7A -173.84(14) no
N1 C4 C6A C8A 6.6(3) no
C11 C4 C6A C7A 6.3(2) no
C11 C4 C6A C8A -173.25(15) no
N1 C5 C6B C7B -178.75(14) no
N1 C5 C6B C8B .0(2) no
C16 C5 C6B C7B .9(2) no
C16 C5 C6B C8B 179.65(14) no
C2 C3 C21 C22 -1.5(3) yes
C2 C3 C21 C26 176.66(17) yes
C26 C21 C22 C23 -.8(3) no
C3 C21 C22 C23 177.4(2) no
C3 C21 C26 C25 -176.94(17) no
C21 C22 C23 C24 -.4(4) no
C22 C23 C24 C25 1.1(4) no
C23 C24 C25 C26 -.6(3) no
C22 C21 C26 C25 1.3(3) no
C24 C25 C26 C21 -.6(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654608
