# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


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#  This CIF contains data from an original supplementary publication 
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#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_ab47-iiip
_database_code_depnum_ccdc_archive 'CCDC 924716'
#TrackingRef '17817_web_deposit_cif_file_0_ChristophJaniak_1361026650.ab47-iiip_final.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
tetra(4-cyanophenyl)ethylene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H16 N4'
_chemical_formula_sum            'C30 H16 N4'
_chemical_formula_weight         432.27
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   'I 41/a c d'
_symmetry_space_group_name_Hall  '-I 4bd 2c'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+1/4, x+3/4, z+1/4'
'y+1/4, -x+1/4, z+3/4'
'-x+1/2, y, -z'
'x, -y, -z+1/2'
'y+1/4, x+3/4, -z+3/4'
'-y+1/4, -x+1/4, -z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+3/4, x+5/4, z+3/4'
'y+3/4, -x+3/4, z+5/4'
'-x+1, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1'
'y+3/4, x+5/4, -z+5/4'
'-y+3/4, -x+3/4, -z+3/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-1/4, -x-3/4, -z-1/4'
'-y-1/4, x-1/4, -z-3/4'
'x-1/2, -y, z'
'-x, y, z-1/2'
'-y-1/4, -x-3/4, z-3/4'
'y-1/4, x-1/4, z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y+1/4, -x-1/4, -z+1/4'
'-y+1/4, x+1/4, -z-1/4'
'x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'-y+1/4, -x-1/4, z-1/4'
'y+1/4, x+1/4, z+1/4'
_cell_length_a                   22.0767(8)
_cell_length_b                   22.0767(8)
_cell_length_c                   21.1707(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     10318.2(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4210
_cell_measurement_theta_min      4.005
_cell_measurement_theta_max      39.53
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3656
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5672
_exptl_absorpt_correction_T_max  0.7478
_exptl_absorpt_process_details   '(<i>SADABS</i>; Sheldrick, 1996)'
_exptl_special_details           
;
Several crystals of the compound were measured both at room and
low temperature.
Because of the high symmetry not only small crystals but also larger
crystals of the size up to 0.3 x 0.3 x 0.2 did not diffract above a
2Theta angle of 77 deg.
For this reason it was decided to limit the 2Theta angle to 79 deg for
the given measurement, which causes the Alerts level A:
"ratio of reflections to parameters < 6",
"value of sine(theta_max)/wavelength is less than 0.550" and
"poor data / parameter ratio".
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10906
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         39.53
_reflns_number_total             753
_reflns_number_gt                665
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
'SHELXL-97 (Sheldrick, 2008), PLATON (Spek, 2009)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact, 2009)'
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.250 -0.004 437 101 ' '
2 0.000 0.750 -0.017 437 101 ' '
3 0.500 0.250 -0.021 437 101 ' '
4 0.500 0.750 -0.008 437 101 ' '
_platon_squeeze_details          
;
The unit cell contains 4 ethanol molecules which have been treated as
a diffuse contribution to the overall scattering without specific atom
positions by SQUEEZE/PLATON
;
_iucr_refine_instructions_details 
;
TITL AB47-II in I4(1)/acd
CELL 1.54178 22.0767 22.0767 21.1707 90.000 90.000 90.000
ZERR 16.00 0.0008 0.0008 0.0010 0.000 0.000 0.000
LATT 2
SYMM 1/2 - X, - Y, 1/2 + Z
SYMM 1/4 - Y, 3/4 + X, 1/4 + Z
SYMM 1/4 + Y, 1/4 - X, 3/4 + Z
SYMM 1/2 - X, Y, - Z
SYMM X, - Y, 1/2 - Z
SYMM 1/4 + Y, 3/4 + X, 3/4 - Z
SYMM 1/4 - Y, 1/4 - X, 1/4 - Z
SFAC C H N O
UNIT 488 280 64 4
TEMP -100.00
MERG 2
FMAP 2
PLAN 1
ACTA
BOND $H
L.S. 40
WGHT 0.086300 29.228500
EXTI 0.000025
FVAR 0.36125
C1 1 0.105125 0.067417 0.920077 11.00000 0.07836 0.07405 =
0.05675 -0.00762 -0.00613 -0.00289
C2 1 0.132108 0.109036 0.882918 11.00000 0.09273 0.07164 =
0.06612 -0.01099 -0.02640 0.03844
AFIX 43
H2 2 0.108724 0.141167 0.865703 11.00000 -1.20000
AFIX 0
C3 1 0.192660 0.105684 0.869637 11.00000 0.09271 0.04713 =
0.06940 0.00370 -0.01264 0.00413
C4 1 0.226629 0.057477 0.893961 11.00000 0.03186 0.06584 =
0.07396 -0.00065 -0.00078 -0.02071
C5 1 0.200339 0.014615 0.930812 11.00000 0.03295 0.05477 =
0.06766 -0.00887 0.00872 -0.00380
C6 1 0.138719 0.019138 0.943951 11.00000 0.09349 0.04382 =
0.04488 0.00195 0.00197 -0.02237
C7 1 0.040468 0.071744 0.933815 11.00000 0.06405 0.14945 =
0.09055 -0.05139 -0.00457 0.01584
C8 1 0.293723 0.043723 0.875000 10.50000 0.12315 0.12315 =
0.06248 0.05187 -0.05187 -0.08426
C9 1 0.333157 0.083157 0.875000 10.50000 0.11790 0.11790 =
0.06485 0.02733 -0.02733 -0.00870
C10 1 0.324161 0.149498 0.899027 11.00000 0.08883 0.06357 =
0.06362 0.00104 -0.01550 0.00557
C11 1 0.330127 0.196647 0.855899 11.00000 0.12247 0.09151 =
0.06478 0.02598 -0.01206 -0.00560
AFIX 43
H11 2 0.333772 0.188317 0.812039 11.00000 -1.20000
AFIX 0
C12 1 0.330689 0.254236 0.876916 11.00000 0.11815 0.06382 =
0.11042 0.02661 -0.04128 -0.02506
AFIX 43
H12A 2 0.333552 0.286866 0.847814 11.00000 -1.20000
AFIX 0
C13 1 0.327176 0.265355 0.939310 11.00000 0.16772 0.03623 =
0.10562 -0.00438 -0.06402 -0.01972
C14 1 0.321027 0.219120 0.982371 11.00000 0.15569 0.05746 =
0.08561 0.01320 -0.03703 0.00451
AFIX 43
H14A 2 0.317903 0.227717 1.026219 11.00000 -1.20000
AFIX 0
C15 1 0.319466 0.160418 0.961166 11.00000 0.09568 0.04826 =
0.07304 0.01269 -0.01589 -0.00307
C16 1 0.331723 0.325621 0.958411 11.00000 0.34304 0.07451 =
0.14996 0.01566 -0.13517 -0.00837
N1 3 -0.008762 0.077001 0.945833 11.00000 0.05803 0.25704 =
0.14642 -0.08191 -0.02067 0.03880
N2 3 0.331115 0.376017 0.976665 11.00000 0.66205 0.07920 =
0.21653 0.00337 -0.25616 -0.01788
H3 2 0.220734 0.131820 0.839572 11.00000 0.08212
H5 2 0.227958 -0.028340 0.947218 11.00000 0.08982
H6 2 0.121694 -0.007839 0.970382 11.00000 0.01044
H15 2 0.313720 0.126842 0.990629 11.00000 0.06880
HKLF 4
REM AB47-II in I4(1)/acd
REM R1 = 0.0592 for 665 Fo > 4sig(Fo) and 0.0660 for all 753 data
REM 172 parameters refined using 0 restraints
END
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0863P)^2^+29.2285P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.000025(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         753
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1693
_refine_ls_wR_factor_gt          0.1643
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1051(4) 0.0674(6) 0.9201(5) 0.070(2) Uani 1 1 d . . .
C2 C 0.1321(6) 0.1090(4) 0.8829(5) 0.077(2) Uani 1 1 d . . .
H2 H 0.1087 0.1412 0.8657 0.092 Uiso 1 1 calc R . .
C3 C 0.1927(6) 0.1057(4) 0.8696(3) 0.070(2) Uani 1 1 d . . .
C4 C 0.2266(3) 0.0575(5) 0.8940(4) 0.057(2) Uani 1 1 d . . .
C5 C 0.2003(5) 0.0146(4) 0.9308(4) 0.0518(19) Uani 1 1 d . . .
C6 C 0.1387(6) 0.0191(4) 0.9440(4) 0.061(2) Uani 1 1 d . . .
C7 C 0.0405(5) 0.0717(3) 0.9338(3) 0.101(3) Uani 1 1 d . . .
C8 C 0.2937(6) 0.0437(6) 0.8750 0.103(6) Uani 1 2 d S . .
C9 C 0.3332(7) 0.0832(7) 0.8750 0.100(4) Uani 1 2 d S . .
C10 C 0.3242(3) 0.1495(4) 0.8990(6) 0.072(2) Uani 1 1 d . . .
C11 C 0.3301(3) 0.1966(7) 0.8559(4) 0.093(2) Uani 1 1 d . . .
H11 H 0.3338 0.1883 0.8120 0.112 Uiso 1 1 calc R . .
C12 C 0.3307(3) 0.2542(6) 0.8769(7) 0.097(3) Uani 1 1 d . . .
H12A H 0.3336 0.2869 0.8478 0.117 Uiso 1 1 calc R . .
C13 C 0.3272(4) 0.2654(4) 0.9393(7) 0.103(3) Uani 1 1 d . . .
C14 C 0.3210(3) 0.2191(7) 0.9824(4) 0.100(3) Uani 1 1 d . . .
H14A H 0.3179 0.2277 1.0262 0.120 Uiso 1 1 calc R . .
C15 C 0.3195(3) 0.1604(5) 0.9612(6) 0.072(2) Uani 1 1 d . . .
C16 C 0.3317(6) 0.3256(7) 0.9584(5) 0.189(5) Uani 1 1 d . . .
N1 N -0.0088(3) 0.0770(4) 0.9458(4) 0.154(4) Uani 1 1 d . . .
N2 N 0.3311(7) 0.3760(4) 0.9767(5) 0.319(9) Uani 1 1 d . . .
H3 H 0.221(3) 0.132(3) 0.840(3) 0.08(2) Uiso 1 1 d . . .
H5 H 0.228(3) -0.028(3) 0.947(2) 0.090(19) Uiso 1 1 d . . .
H6 H 0.1217(17) -0.0078(18) 0.9704(18) 0.010(16) Uiso 1 1 d . . .
H15 H 0.314(2) 0.127(3) 0.991(3) 0.07(2) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.078(8) 0.074(6) 0.057(5) -0.008(5) -0.006(6) -0.003(8)
C2 0.093(9) 0.072(7) 0.066(6) -0.011(6) -0.026(5) 0.038(6)
C3 0.093(9) 0.047(6) 0.069(5) 0.004(4) -0.013(6) 0.004(6)
C4 0.032(6) 0.066(6) 0.074(5) -0.001(5) -0.001(5) -0.021(7)
C5 0.033(7) 0.055(7) 0.068(5) -0.009(5) 0.009(4) -0.004(5)
C6 0.093(10) 0.044(7) 0.045(5) 0.002(5) 0.002(6) -0.022(6)
C7 0.064(7) 0.149(7) 0.091(6) -0.051(5) -0.005(5) 0.016(6)
C8 0.123(8) 0.123(8) 0.062(7) 0.052(7) -0.052(7) -0.084(14)
C9 0.118(6) 0.118(6) 0.065(8) 0.027(6) -0.027(6) -0.009(11)
C10 0.089(5) 0.064(9) 0.064(8) 0.001(8) -0.016(4) 0.006(4)
C11 0.122(6) 0.092(7) 0.065(6) 0.026(9) -0.012(4) -0.006(5)
C12 0.118(6) 0.064(9) 0.110(11) 0.027(7) -0.041(5) -0.025(5)
C13 0.168(8) 0.036(9) 0.106(9) -0.004(9) -0.064(6) -0.020(4)
C14 0.156(7) 0.057(7) 0.086(7) 0.013(9) -0.037(5) 0.005(4)
C15 0.096(5) 0.048(9) 0.073(9) 0.013(7) -0.016(4) -0.003(4)
C16 0.343(16) 0.075(9) 0.150(10) 0.016(8) -0.135(9) -0.008(8)
N1 0.058(5) 0.257(9) 0.146(6) -0.082(6) -0.021(5) 0.039(5)
N2 0.66(2) 0.079(7) 0.217(11) 0.003(7) -0.256(13) -0.018(10)
_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.348(9) . ?
C1 C6 1.393(9) . ?
C1 C7 1.460(11) . ?
C2 C3 1.368(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(9) . ?
C3 H3 1.06(6) . ?
C4 C5 1.357(8) . ?
C4 C8 1.564(8) . ?
C5 C6 1.392(8) . ?
C5 H5 1.18(6) . ?
C6 H6 0.90(4) . ?
C7 N1 1.122(9) . ?
C8 C9 1.231(13) . ?
C8 C4 1.564(8) 7_546 ?
C9 C10 1.563(10) 7_546 ?
C9 C10 1.563(10) . ?
C10 C15 1.341(8) . ?
C10 C11 1.391(9) . ?
C11 C12 1.347(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.346(10) . ?
C12 H12A 0.9500 . ?
C13 C14 1.375(10) . ?
C13 C16 1.394(13) . ?
C14 C15 1.372(9) . ?
C14 H14A 0.9500 . ?
C15 H15 0.98(6) . ?
C16 N2 1.178(13) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.9(7) . . ?
C2 C1 C7 120.2(12) . . ?
C6 C1 C7 119.9(11) . . ?
C1 C2 C3 121.0(6) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 119.3(7) . . ?
C2 C3 H3 132(3) . . ?
C4 C3 H3 109(3) . . ?
C5 C4 C3 120.8(7) . . ?
C5 C4 C8 114.7(9) . . ?
C3 C4 C8 124.1(9) . . ?
C4 C5 C6 118.9(6) . . ?
C4 C5 H5 121(3) . . ?
C6 C5 H5 120(3) . . ?
C5 C6 C1 120.2(7) . . ?
C5 C6 H6 119(2) . . ?
C1 C6 H6 121(3) . . ?
N1 C7 C1 177.3(8) . . ?
C9 C8 C4 122.2(5) . 7_546 ?
C9 C8 C4 122.2(5) . . ?
C4 C8 C4 115.7(10) 7_546 . ?
C8 C9 C10 124.9(7) . 7_546 ?
C8 C9 C10 124.9(7) . . ?
C10 C9 C10 110.1(14) 7_546 . ?
C15 C10 C11 121.1(8) . . ?
C15 C10 C9 119.8(9) . . ?
C11 C10 C9 118.4(11) . . ?
C12 C11 C10 119.4(7) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 119.7(8) . . ?
C13 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C12 C13 C14 121.4(8) . . ?
C12 C13 C16 117.0(13) . . ?
C14 C13 C16 121.5(13) . . ?
C15 C14 C13 119.1(8) . . ?
C15 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
C10 C15 C14 119.3(8) . . ?
C10 C15 H15 120(3) . . ?
C14 C15 H15 121(3) . . ?
N2 C16 C13 174.7(16) . . ?
_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        39.53
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.033