# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A
_database_code_depnum_ccdc_archive 'CCDC 1431281'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;
#data_eca7n 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1,1-Dicyano-2,2-bis(4-dimethylaminophenyl)ethylene
;
_chemical_formula_moiety         'C20 H20 N4'
_chemical_formula_sum            'C20 H20 N4'
_chemical_formula_weight         316.40

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.9266(11)
_cell_length_b                   9.3889(8)
_cell_length_c                   15.6279(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.4980(10)
_cell_angle_gamma                90.00
_cell_volume                     1735.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2933
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      24.16

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD area detector'
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14369
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         27.93
_reflns_number_total             2074
_reflns_number_gt                1498
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  'SHELXL-97,PARST (Nardelli, 1995)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²+0.6728P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2074
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
N1 N 0.62983(13) -0.18499(15) 0.66857(9) 0.0722(4) Uani 1 1 d . . .
N2 N 0.66058(11) 0.43494(13) 0.48273(9) 0.0623(4) Uani 1 1 d . . .
C1 C 0.57165(13) -0.11385(15) 0.70291(9) 0.0535(4) Uani 1 1 d . . .
C2 C 0.5000 -0.0310(2) 0.7500 0.0497(4) Uani 1 2 d S . .
C3 C 0.5000 0.1167(2) 0.7500 0.0476(4) Uani 1 2 d S . .
C4 C 0.54503(11) 0.19580(14) 0.68167(8) 0.0475(3) Uani 1 1 d . . .
C5 C 0.52956(12) 0.14996(14) 0.59563(8) 0.0522(3) Uani 1 1 d . . .
H5 H 0.4934 0.0635 0.5823 0.063 Uiso 1 1 calc R . .
C6 C 0.56572(12) 0.22797(15) 0.53062(9) 0.0534(4) Uani 1 1 d . . .
H6 H 0.5521 0.1944 0.4742 0.064 Uiso 1 1 calc R . .
C7 C 0.62321(11) 0.35833(14) 0.54733(9) 0.0493(3) Uani 1 1 d . . .
C8 C 0.63999(12) 0.40423(15) 0.63390(10) 0.0573(4) Uani 1 1 d . . .
H8 H 0.6779 0.4894 0.6478 0.069 Uiso 1 1 calc R . .
C9 C 0.60143(12) 0.32559(15) 0.69797(9) 0.0553(4) Uani 1 1 d . . .
H9 H 0.6132 0.3597 0.7543 0.066 Uiso 1 1 calc R . .
C10 C 0.64385(15) 0.38654(19) 0.39407(10) 0.0692(5) Uani 1 1 d . . .
H10A H 0.6634 0.2875 0.3920 0.104 Uiso 1 1 calc R . .
H10B H 0.6910 0.4408 0.3609 0.104 Uiso 1 1 calc R . .
H10C H 0.5660 0.3992 0.3706 0.104 Uiso 1 1 calc R . .
C11 C 0.71142(17) 0.57401(18) 0.49893(14) 0.0823(6) Uani 1 1 d . . .
H11A H 0.6594 0.6354 0.5231 0.123 Uiso 1 1 calc R . .
H11B H 0.7290 0.6138 0.4457 0.123 Uiso 1 1 calc R . .
H11C H 0.7795 0.5650 0.5387 0.123 Uiso 1 1 calc R . .


_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
N1 C1 1.1458(18) . ?
N2 C7 1.3611(17) . ?
N2 C10 1.447(2) . ?
N2 C11 1.448(2) . ?
C1 C2 1.4285(18) . ?
C2 C3 1.387(3) . ?
C2 C1 1.4285(18) 2_656 ?
C3 C4 1.4594(16) 2_656 ?
C3 C4 1.4594(16) . ?
C4 C9 1.3992(18) . ?
C4 C5 1.4008(18) . ?
C5 C6 1.3671(19) . ?
C6 C7 1.4105(19) . ?
C7 C8 1.409(2) . ?
C8 C9 1.371(2) . ?

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
C7 N2 C10 121.78(13) . . ?
C7 N2 C11 121.14(14) . . ?
C10 N2 C11 116.92(13) . . ?
N1 C1 C2 176.54(15) . . ?
C3 C2 C1 122.98(8) . . ?
C3 C2 C1 122.98(8) . 2_656 ?
C1 C2 C1 114.04(17) . 2_656 ?
C2 C3 C4 120.58(8) . 2_656 ?
C2 C3 C4 120.58(8) . . ?
C4 C3 C4 118.83(16) 2_656 . ?
C9 C4 C5 116.25(12) . . ?
C9 C4 C3 121.60(12) . . ?
C5 C4 C3 122.08(12) . . ?
C6 C5 C4 122.27(13) . . ?
C5 C6 C7 121.34(13) . . ?
N2 C7 C8 122.09(13) . . ?
N2 C7 C6 121.30(13) . . ?
C8 C7 C6 116.61(12) . . ?
C9 C8 C7 121.15(13) . . ?
C8 C9 C4 122.36(13) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.93
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.030

_chemical_name_common            
2-(bis(4-dimethylaminophenyl)methylene)malonitrile
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_B
_database_code_depnum_ccdc_archive 'CCDC 1431282'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;
#data_eca8 
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1,1-Dicyano-2,2-bis(4-dimethylaminophenyl)ethylene
;
_chemical_formula_moiety         'C20 H20 N4'
_chemical_formula_sum            'C20 H20 N4'
_chemical_formula_weight         316.40

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   8.4920(7)
_cell_length_b                   13.9497(11)
_cell_length_c                   15.0750(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.0620(10)
_cell_angle_gamma                90.00
_cell_volume                     1758.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3667
_cell_measurement_theta_min      2.744
_cell_measurement_theta_max      25.527

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'

_exptl_special_details           
; 
 Crystals of different morphology with respect to eca7.
These are extended along one direction while the others are 
quite squared.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD area detector'
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            16782
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         29.82
_reflns_number_total             2531
_reflns_number_gt                1782
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  'SHELXL-97,PARST (Nardelli, 1995)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0608P)²+0.6116P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2531
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1429
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_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
N1 N 0.78396(18) 1.29756(9) 0.65638(9) 0.0709(4) Uani 1 1 d . . .
N2 N 0.62956(15) 0.88502(9) 0.46382(8) 0.0613(3) Uani 1 1 d . . .
C1 C 0.87905(17) 1.24848(9) 0.69583(9) 0.0522(3) Uani 1 1 d . . .
C2 C 1.0000 1.19212(12) 0.7500 0.0467(4) Uani 1 2 d S . .
C3 C 1.0000 1.09251(12) 0.7500 0.0423(4) Uani 1 2 d S . .
C4 C 0.90331(15) 1.03984(8) 0.67616(8) 0.0422(3) Uani 1 1 d . . .
C5 C 0.88183(16) 1.07234(9) 0.58690(8) 0.0472(3) Uani 1 1 d . . .
H5 H 0.9295 1.1297 0.5745 0.057 Uiso 1 1 calc R . .
C6 C 0.79284(16) 1.02241(9) 0.51727(8) 0.0490(3) Uani 1 1 d . . .
H6 H 0.7825 1.0461 0.4589 0.059 Uiso 1 1 calc R . .
C7 C 0.71689(15) 0.93592(9) 0.53269(8) 0.0459(3) Uani 1 1 d . . .
C8 C 0.73759(16) 0.90314(9) 0.62244(9) 0.0508(3) Uani 1 1 d . . .
H8 H 0.6880 0.8466 0.6352 0.061 Uiso 1 1 calc R . .
C9 C 0.82948(16) 0.95291(9) 0.69138(8) 0.0474(3) Uani 1 1 d . . .
H9 H 0.8430 0.9283 0.7496 0.057 Uiso 1 1 calc R . .
C10 C 0.6075(2) 0.91861(15) 0.37169(10) 0.0803(5) Uani 1 1 d . . .
H10A H 0.5478 0.9774 0.3665 0.120 Uiso 1 1 calc R . .
H10B H 0.5500 0.8712 0.3326 0.120 Uiso 1 1 calc R . .
H10C H 0.7099 0.9295 0.3549 0.120 Uiso 1 1 calc R . .
C11 C 0.54271(19) 0.79927(12) 0.48118(11) 0.0696(4) Uani 1 1 d . . .
H11A H 0.6157 0.7539 0.5139 0.104 Uiso 1 1 calc R . .
H11B H 0.4927 0.7715 0.4250 0.104 Uiso 1 1 calc R . .
H11C H 0.4624 0.8158 0.5161 0.104 Uiso 1 1 calc R . .


_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
N1 C1 1.1431(17) . ?
N2 C7 1.3649(16) . ?
N2 C10 1.447(2) . ?
N2 C11 1.453(2) . ?
C1 C2 1.4306(16) . ?
C2 C3 1.390(2) . ?
C2 C1 1.4306(16) 2_756 ?
C3 C4 1.4607(14) 2_756 ?
C3 C4 1.4607(14) . ?
C4 C5 1.4012(16) . ?
C4 C9 1.4023(17) . ?
C5 C6 1.3714(17) . ?
C6 C7 1.4064(18) . ?
C7 C8 1.4097(17) . ?
C8 C9 1.3740(17) . ?

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
C7 N2 C10 121.59(13) . . ?
C7 N2 C11 121.12(12) . . ?
C10 N2 C11 117.05(13) . . ?
N1 C1 C2 175.97(14) . . ?
C3 C2 C1 123.33(8) . . ?
C3 C2 C1 123.33(8) . 2_756 ?
C1 C2 C1 113.34(15) . 2_756 ?
C2 C3 C4 120.19(7) . 2_756 ?
C2 C3 C4 120.20(7) . . ?
C4 C3 C4 119.61(14) 2_756 . ?
C5 C4 C9 116.74(11) . . ?
C5 C4 C3 122.04(11) . . ?
C9 C4 C3 121.20(11) . . ?
C6 C5 C4 122.17(12) . . ?
C5 C6 C7 121.10(11) . . ?
N2 C7 C6 121.64(12) . . ?
N2 C7 C8 121.42(12) . . ?
C6 C7 C8 116.93(11) . . ?
C9 C8 C7 121.41(12) . . ?
C8 C9 C4 121.62(11) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.82
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.032

_chemical_name_common            
2-(bis(4-dimethylaminophenyl)methylene)malonitrile
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_C
_database_code_depnum_ccdc_archive 'CCDC 1431283'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;
#data_lucia915

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
1,1-Dicyano-2,2-bis(4-dimethylaminophenyl)ethylene
;
_chemical_formula_moiety         'C20 H20 N4'
_chemical_formula_sum            'C20 H20 N4'
_chemical_formula_weight         316.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.7959(12)
_cell_length_b                   9.9417(12)
_cell_length_c                   17.678(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.4780(10)
_cell_angle_gamma                90
_cell_volume                     1716.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6369
_cell_measurement_theta_min      2.311
_cell_measurement_theta_max      26.373

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD area detector'
_diffrn_standards_decay_%        0
_diffrn_reflns_number            28874
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.155
_diffrn_reflns_theta_max         32.200
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             11008
_reflns_number_gt                8262
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_max     0.875
_reflns_Friedel_fraction_full    0.995

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  'SHELXL-97,PARST (Nardelli, 1995)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+0.2532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_abs_structure_details 
;
 Flack x determined using 3039 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.4(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         11007
_refine_ls_number_parameters     433
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3424(3) -0.3915(3) 0.93370(13) 0.0472(6) Uani 1 1 d . . . . .
N2 N -0.2300(2) -0.6641(2) 0.88762(12) 0.0339(5) Uani 1 1 d . . . . .
N3 N 0.5791(3) -0.3706(3) 0.74500(13) 0.0479(7) Uani 1 1 d . . . . .
N4 N 0.35220(18) -0.7221(2) 0.45792(10) 0.0245(4) Uani 1 1 d . . . . .
N5 N 0.3868(2) 0.1337(3) 0.89386(15) 0.0512(7) Uani 1 1 d . . . . .
N6 N -0.1949(2) -0.1722(2) 0.92975(11) 0.0306(5) Uani 1 1 d . . . . .
N7 N 0.5643(2) 0.0304(3) 0.69193(13) 0.0391(5) Uani 1 1 d . . . . .
N8 N 0.1697(2) -0.1771(2) 0.42465(10) 0.0272(4) Uani 1 1 d . . . . .
C1 C 0.3441(2) -0.4235(3) 0.87178(14) 0.0303(5) Uani 1 1 d . . . . .
C2 C 0.3555(2) -0.4610(2) 0.79395(12) 0.0255(5) Uani 1 1 d . . . . .
C3 C 0.2596(2) -0.5370(2) 0.75280(12) 0.0221(4) Uani 1 1 d . . . . .
C4 C 0.1272(2) -0.5659(2) 0.78303(12) 0.0216(4) Uani 1 1 d . . . . .
C5 C 0.0515(2) -0.4665(2) 0.81747(12) 0.0247(5) Uani 1 1 d . . . . .
H5 H 0.0836 -0.3763 0.8187 0.030 Uiso 1 1 calc R U . . .
C6 C -0.0686(2) -0.4970(2) 0.84963(13) 0.0261(5) Uani 1 1 d . . . . .
H6 H -0.1195 -0.4272 0.8710 0.031 Uiso 1 1 calc R U . . .
C7 C -0.1169(2) -0.6306(2) 0.85116(12) 0.0245(4) Uani 1 1 d . . . . .
C8 C -0.0424(2) -0.7296(2) 0.81448(12) 0.0241(5) Uani 1 1 d . . . . .
H8 H -0.0735 -0.8202 0.8134 0.029 Uiso 1 1 calc R U . . .
C9 C 0.0746(2) -0.6968(2) 0.78035(12) 0.0227(4) Uani 1 1 d . . . . .
H9 H 0.1207 -0.7646 0.7543 0.027 Uiso 1 1 calc R U . . .
C10 C -0.2758(3) -0.8030(3) 0.88835(16) 0.0400(7) Uani 1 1 d . . . . .
H10A H -0.3576 -0.8096 0.9167 0.060 Uiso 1 1 calc R U . . .
H10B H -0.2978 -0.8338 0.8361 0.060 Uiso 1 1 calc R U . . .
H10C H -0.2030 -0.8595 0.9127 0.060 Uiso 1 1 calc R U . . .
C11 C -0.3070(3) -0.5620(3) 0.92534(16) 0.0408(7) Uani 1 1 d . . . . .
H11A H -0.3842 -0.6044 0.9482 0.061 Uiso 1 1 calc R U . . .
H11B H -0.2471 -0.5183 0.9650 0.061 Uiso 1 1 calc R U . . .
H11C H -0.3416 -0.4946 0.8882 0.061 Uiso 1 1 calc R U . . .
C12 C 0.4783(3) -0.4121(3) 0.76453(13) 0.0318(5) Uani 1 1 d . . . . .
C13 C 0.2851(2) -0.5903(2) 0.67804(12) 0.0211(4) Uani 1 1 d . . . . .
C14 C 0.4138(2) -0.6377(2) 0.66020(13) 0.0244(4) Uani 1 1 d . . . . .
H14 H 0.4872 -0.6394 0.6986 0.029 Uiso 1 1 calc R U . . .
C15 C 0.4360(2) -0.6817(2) 0.58839(13) 0.0243(5) Uani 1 1 d . . . . .
H15 H 0.5237 -0.7151 0.5785 0.029 Uiso 1 1 calc R U . . .
C16 C 0.3307(2) -0.6779(2) 0.52897(12) 0.0215(4) Uani 1 1 d . . . . .
C17 C 0.2012(2) -0.6309(2) 0.54697(12) 0.0223(4) Uani 1 1 d . . . . .
H17 H 0.1282 -0.6263 0.5084 0.027 Uiso 1 1 calc R U . . .
C18 C 0.1793(2) -0.5916(2) 0.61982(12) 0.0220(4) Uani 1 1 d . . . . .
H18 H 0.0900 -0.5645 0.6309 0.026 Uiso 1 1 calc R U . . .
C19 C 0.4878(2) -0.7647(3) 0.43983(15) 0.0368(6) Uani 1 1 d . . . . .
H19A H 0.4846 -0.7931 0.3866 0.055 Uiso 1 1 calc R U . . .
H19B H 0.5521 -0.6896 0.4480 0.055 Uiso 1 1 calc R U . . .
H19C H 0.5183 -0.8401 0.4726 0.055 Uiso 1 1 calc R U . . .
C20 C 0.2478(2) -0.7040(3) 0.39552(13) 0.0273(5) Uani 1 1 d . . . . .
H20A H 0.2804 -0.7415 0.3489 0.041 Uiso 1 1 calc R U . . .
H20B H 0.1637 -0.7505 0.4073 0.041 Uiso 1 1 calc R U . . .
H20C H 0.2288 -0.6079 0.3883 0.041 Uiso 1 1 calc R U . . .
C21 C 0.3662(2) 0.0773(3) 0.83771(15) 0.0318(5) Uani 1 1 d . . . . .
C22 C 0.3471(2) 0.0127(2) 0.76521(13) 0.0255(5) Uani 1 1 d . . . . .
C23 C 0.2277(2) -0.0518(2) 0.73895(12) 0.0217(4) Uani 1 1 d . . . . .
C24 C 0.1204(2) -0.0849(2) 0.78848(12) 0.0215(4) Uani 1 1 d . . . . .
C25 C 0.1473(2) -0.1128(2) 0.86630(13) 0.0263(5) Uani 1 1 d . . . . .
H25 H 0.2393 -0.1115 0.8876 0.032 Uiso 1 1 calc R U . . .
C26 C 0.0449(2) -0.1419(2) 0.91220(12) 0.0268(5) Uani 1 1 d . . . . .
H26 H 0.0676 -0.1624 0.9641 0.032 Uiso 1 1 calc R U . . .
C27 C -0.0945(2) -0.1419(2) 0.88354(12) 0.0248(5) Uani 1 1 d . . . . .
C28 C -0.1224(2) -0.1140(2) 0.80550(13) 0.0244(5) Uani 1 1 d . . . . .
H28 H -0.2144 -0.1132 0.7841 0.029 Uiso 1 1 calc R U . . .
C29 C -0.0178(2) -0.0878(2) 0.76016(12) 0.0229(4) Uani 1 1 d . . . . .
H29 H -0.0396 -0.0711 0.7077 0.027 Uiso 1 1 calc R U . . .
C30 C -0.1609(3) -0.1941(3) 1.01053(14) 0.0428(7) Uani 1 1 d . . . . .
H30A H -0.2446 -0.2147 1.0352 0.064 Uiso 1 1 calc R U . . .
H30B H -0.0968 -0.2695 1.0176 0.064 Uiso 1 1 calc R U . . .
H30C H -0.1186 -0.1127 1.0331 0.064 Uiso 1 1 calc R U . . .
C31 C -0.3396(3) -0.1625(3) 0.90472(16) 0.0392(6) Uani 1 1 d . . . . .
H31A H -0.3945 -0.1886 0.9463 0.059 Uiso 1 1 calc R U . . .
H31B H -0.3615 -0.0697 0.8895 0.059 Uiso 1 1 calc R U . . .
H31C H -0.3601 -0.2227 0.8614 0.059 Uiso 1 1 calc R U . . .
C32 C 0.4653(2) 0.0213(3) 0.72189(13) 0.0278(5) Uani 1 1 d . . . . .
C33 C 0.2069(2) -0.0847(2) 0.65755(12) 0.0205(4) Uani 1 1 d . . . . .
C34 C 0.2325(2) 0.0117(2) 0.60289(12) 0.0237(4) Uani 1 1 d . . . . .
H34 H 0.2621 0.0989 0.6189 0.028 Uiso 1 1 calc R U . . .
C35 C 0.2160(2) -0.0165(2) 0.52647(13) 0.0238(4) Uani 1 1 d . . . . .
H35 H 0.2315 0.0522 0.4908 0.029 Uiso 1 1 calc R U . . .
C36 C 0.1765(2) -0.1456(2) 0.50043(12) 0.0207(4) Uani 1 1 d . . . . .
C37 C 0.1466(2) -0.2419(2) 0.55556(12) 0.0224(4) Uani 1 1 d . . . . .
H37 H 0.1167 -0.3292 0.5399 0.027 Uiso 1 1 calc R U . . .
C38 C 0.1602(2) -0.2109(2) 0.63185(12) 0.0227(4) Uani 1 1 d . . . . .
H38 H 0.1373 -0.2767 0.6677 0.027 Uiso 1 1 calc R U . . .
C39 C 0.1395(3) -0.3133(3) 0.39917(14) 0.0349(6) Uani 1 1 d . . . . .
H39A H 0.1387 -0.3172 0.3437 0.052 Uiso 1 1 calc R U . . .
H39B H 0.2097 -0.3745 0.4218 0.052 Uiso 1 1 calc R U . . .
H39C H 0.0496 -0.3402 0.4148 0.052 Uiso 1 1 calc R U . . .
C40 C 0.2051(3) -0.0772(3) 0.36920(13) 0.0310(5) Uani 1 1 d . . . . .
H40A H 0.1945 -0.1165 0.3182 0.047 Uiso 1 1 calc R U . . .
H40B H 0.1443 0.0007 0.3715 0.047 Uiso 1 1 calc R U . . .
H40C H 0.3002 -0.0487 0.3805 0.047 Uiso 1 1 calc R U . . .


_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
N1 C1 1.142(3) . ?
N2 C7 1.366(3) . ?
N2 C10 1.453(4) . ?
N2 C11 1.457(3) . ?
N3 C12 1.147(3) . ?
N4 C16 1.362(3) . ?
N4 C19 1.454(3) . ?
N4 C20 1.456(3) . ?
N5 C21 1.144(3) . ?
N6 C27 1.360(3) . ?
N6 C31 1.454(3) . ?
N6 C30 1.457(3) . ?
N7 C32 1.144(3) . ?
N8 C36 1.372(3) . ?
N8 C39 1.450(3) . ?
N8 C40 1.456(3) . ?
C1 C2 1.438(3) . ?
C2 C3 1.369(3) . ?
C2 C12 1.433(3) . ?
C3 C13 1.463(3) . ?
C3 C4 1.470(3) . ?
C4 C9 1.399(3) . ?
C4 C5 1.403(3) . ?
C5 C6 1.380(3) . ?
C6 C7 1.410(3) . ?
C7 C8 1.414(3) . ?
C8 C9 1.375(3) . ?
C13 C18 1.402(3) . ?
C13 C14 1.405(3) . ?
C14 C15 1.376(3) . ?
C15 C16 1.414(3) . ?
C16 C17 1.411(3) . ?
C17 C18 1.379(3) . ?
C21 C22 1.433(3) . ?
C22 C23 1.382(3) . ?
C22 C32 1.440(3) . ?
C23 C24 1.457(3) . ?
C23 C33 1.474(3) . ?
C24 C29 1.407(3) . ?
C24 C25 1.408(3) . ?
C25 C26 1.369(3) . ?
C26 C27 1.419(3) . ?
C27 C28 1.413(3) . ?
C28 C29 1.374(3) . ?
C33 C34 1.398(3) . ?
C33 C38 1.399(3) . ?
C34 C35 1.377(3) . ?
C35 C36 1.407(3) . ?
C36 C37 1.414(3) . ?
C37 C38 1.380(3) . ?

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
C7 N2 C10 119.9(2) . . ?
C7 N2 C11 120.9(2) . . ?
C10 N2 C11 119.1(2) . . ?
C16 N4 C19 120.43(19) . . ?
C16 N4 C20 120.57(19) . . ?
C19 N4 C20 118.01(19) . . ?
C27 N6 C31 122.4(2) . . ?
C27 N6 C30 120.1(2) . . ?
C31 N6 C30 116.8(2) . . ?
C36 N8 C39 120.66(19) . . ?
C36 N8 C40 120.34(19) . . ?
C39 N8 C40 118.76(19) . . ?
N1 C1 C2 176.2(3) . . ?
C3 C2 C12 123.7(2) . . ?
C3 C2 C1 123.4(2) . . ?
C12 C2 C1 112.9(2) . . ?
C2 C3 C13 121.43(19) . . ?
C2 C3 C4 120.21(19) . . ?
C13 C3 C4 118.36(19) . . ?
C9 C4 C5 117.7(2) . . ?
C9 C4 C3 120.18(19) . . ?
C5 C4 C3 122.1(2) . . ?
C6 C5 C4 121.4(2) . . ?
C5 C6 C7 120.9(2) . . ?
N2 C7 C6 121.6(2) . . ?
N2 C7 C8 120.9(2) . . ?
C6 C7 C8 117.5(2) . . ?
C9 C8 C7 120.9(2) . . ?
C8 C9 C4 121.5(2) . . ?
N3 C12 C2 176.2(3) . . ?
C18 C13 C14 117.2(2) . . ?
C18 C13 C3 119.87(19) . . ?
C14 C13 C3 122.92(19) . . ?
C15 C14 C13 121.6(2) . . ?
C14 C15 C16 121.2(2) . . ?
N4 C16 C17 121.4(2) . . ?
N4 C16 C15 121.32(19) . . ?
C17 C16 C15 117.24(19) . . ?
C18 C17 C16 120.84(19) . . ?
C17 C18 C13 121.9(2) . . ?
N5 C21 C22 176.1(3) . . ?
C23 C22 C21 123.8(2) . . ?
C23 C22 C32 122.9(2) . . ?
C21 C22 C32 113.2(2) . . ?
C22 C23 C24 122.3(2) . . ?
C22 C23 C33 118.66(19) . . ?
C24 C23 C33 119.05(19) . . ?
C29 C24 C25 116.4(2) . . ?
C29 C24 C23 120.66(19) . . ?
C25 C24 C23 122.9(2) . . ?
C26 C25 C24 122.1(2) . . ?
C25 C26 C27 121.2(2) . . ?
N6 C27 C28 122.5(2) . . ?
N6 C27 C26 120.4(2) . . ?
C28 C27 C26 117.1(2) . . ?
C29 C28 C27 120.7(2) . . ?
C28 C29 C24 122.5(2) . . ?
N7 C32 C22 175.4(3) . . ?
C34 C33 C38 117.55(19) . . ?
C34 C33 C23 120.28(19) . . ?
C38 C33 C23 122.17(19) . . ?
C35 C34 C33 121.7(2) . . ?
C34 C35 C36 121.0(2) . . ?
N8 C36 C35 121.3(2) . . ?
N8 C36 C37 121.4(2) . . ?
C35 C36 C37 117.32(19) . . ?
C38 C37 C36 120.9(2) . . ?
C37 C38 C33 121.5(2) . . ?

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.043



_chemical_name_common            
2-(bis(4-dimethylaminophenyl)methylene)malonitrile
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_D
_database_code_depnum_ccdc_archive 'CCDC 1431284'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;
#data_eca10lt 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'1,1-Dicyano-2,2-bis(4-dimethylaminophenyl)ethylene dichloromethane solvate'
_chemical_formula_moiety         'C20 H20 N4, C H2 Cl2'
_chemical_formula_sum            'C21 H22 Cl2 N4'
_chemical_formula_weight         401.33

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   12.5444(8)
_cell_length_b                   22.3085(14)
_cell_length_c                   7.5898(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.3500(10)
_cell_angle_gamma                90.00
_cell_volume                     2048.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4027
_cell_measurement_theta_min      2.483
_cell_measurement_theta_max      21.834

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'

_exptl_special_details           
; 
 Crystals decay in few days owing to solvent loss.
 The crystal used for data collection has been covered by
 perfluorinated oil to prevent decay.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD area detector'
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            23624
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         23.41
_reflns_number_total             2993
_reflns_number_gt                2360
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  'SHELXL-97,PARST (Nardelli, 1995)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²+2.7655P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2993
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1360
_refine_ls_wR_factor_gt          0.1253
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_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
N1 N 1.0228(2) 0.75537(12) 0.1650(4) 0.0420(7) Uani 1 1 d . . .
N2 N 1.03805(19) 0.47184(10) 0.2512(3) 0.0309(6) Uani 1 1 d . . .
N3 N 0.7334(2) 0.83724(11) 0.2544(3) 0.0363(6) Uani 1 1 d . . .
N4 N 0.31828(19) 0.68175(12) 0.1390(4) 0.0383(6) Uani 1 1 d . . .
C1 C 0.9377(2) 0.74604(12) 0.1898(4) 0.0291(7) Uani 1 1 d . . .
C2 C 0.8292(2) 0.73767(12) 0.2129(4) 0.0253(6) Uani 1 1 d . . .
C3 C 0.7800(2) 0.68220(12) 0.2110(3) 0.0243(6) Uani 1 1 d . . .
C4 C 0.8450(2) 0.62716(12) 0.2306(4) 0.0244(6) Uani 1 1 d . . .
C5 C 0.9546(2) 0.62446(12) 0.3378(4) 0.0253(6) Uani 1 1 d . . .
H5 H 0.9864 0.6589 0.4049 0.030 Uiso 1 1 calc R . .
C6 C 1.0173(2) 0.57336(12) 0.3486(4) 0.0258(6) Uani 1 1 d . . .
H6 H 1.0909 0.5731 0.4243 0.031 Uiso 1 1 calc R . .
C7 C 0.9745(2) 0.52131(12) 0.2495(4) 0.0258(6) Uani 1 1 d . . .
C8 C 0.8626(2) 0.52329(12) 0.1471(4) 0.0281(6) Uani 1 1 d . . .
H8 H 0.8296 0.4886 0.0829 0.034 Uiso 1 1 calc R . .
C9 C 0.8007(2) 0.57459(12) 0.1389(4) 0.0272(6) Uani 1 1 d . . .
H9 H 0.7257 0.5744 0.0690 0.033 Uiso 1 1 calc R . .
C10 C 1.1546(2) 0.47190(13) 0.3494(4) 0.0356(7) Uani 1 1 d . . .
H10A H 1.1905 0.5073 0.3143 0.053 Uiso 1 1 calc R . .
H10B H 1.1898 0.4356 0.3188 0.053 Uiso 1 1 calc R . .
H10C H 1.1619 0.4729 0.4811 0.053 Uiso 1 1 calc R . .
C11 C 0.9901(3) 0.41616(13) 0.1670(4) 0.0383(8) Uani 1 1 d . . .
H11A H 0.9613 0.4220 0.0349 0.057 Uiso 1 1 calc R . .
H11B H 0.9297 0.4040 0.2189 0.057 Uiso 1 1 calc R . .
H11C H 1.0469 0.3849 0.1902 0.057 Uiso 1 1 calc R . .
C12 C 0.7740(2) 0.79258(13) 0.2337(4) 0.0269(6) Uani 1 1 d . . .
C13 C 0.6601(2) 0.67951(11) 0.1877(4) 0.0238(6) Uani 1 1 d . . .
C14 C 0.6125(2) 0.63955(12) 0.2864(4) 0.0262(6) Uani 1 1 d . . .
H14 H 0.6583 0.6116 0.3663 0.031 Uiso 1 1 calc R . .
C15 C 0.5004(2) 0.63983(12) 0.2706(4) 0.0290(7) Uani 1 1 d . . .
H15 H 0.4708 0.6125 0.3413 0.035 Uiso 1 1 calc R . .
C16 C 0.4289(2) 0.67972(12) 0.1518(4) 0.0281(6) Uani 1 1 d . . .
C17 C 0.4765(2) 0.71828(12) 0.0474(4) 0.0286(6) Uani 1 1 d . . .
H17 H 0.4305 0.7449 -0.0371 0.034 Uiso 1 1 calc R . .
C18 C 0.5887(2) 0.71806(12) 0.0655(4) 0.0265(6) Uani 1 1 d . . .
H18 H 0.6184 0.7447 -0.0068 0.032 Uiso 1 1 calc R . .
C19 C 0.2667(3) 0.63630(17) 0.2244(5) 0.0533(10) Uani 1 1 d . . .
H19A H 0.2722 0.5973 0.1678 0.080 Uiso 1 1 calc R . .
H19B H 0.1887 0.6464 0.2082 0.080 Uiso 1 1 calc R . .
H19C H 0.3042 0.6343 0.3551 0.080 Uiso 1 1 calc R . .
C20 C 0.2456(3) 0.71873(19) 0.0000(5) 0.0575(10) Uani 1 1 d . . .
H20A H 0.1694 0.7148 0.0094 0.086 Uiso 1 1 calc R . .
H20B H 0.2495 0.7055 -0.1213 0.086 Uiso 1 1 calc R . .
H20C H 0.2688 0.7607 0.0184 0.086 Uiso 1 1 calc R . .
C21 C 0.4919(3) 0.9128(2) 0.2997(6) 0.0687(12) Uani 1 1 d . . .
H21A H 0.5176 0.9068 0.4335 0.082 Uiso 1 1 calc R . .
H21B H 0.5194 0.8787 0.2406 0.082 Uiso 1 1 calc R . .
Cl1 Cl 0.34764(10) 0.91219(8) 0.23390(18) 0.1067(5) Uani 1 1 d . . .
Cl2 Cl 0.54756(15) 0.97758(7) 0.2440(3) 0.1463(8) Uani 1 1 d . . .


_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
N1 C1 1.150(4) . ?
N2 C7 1.360(3) . ?
N2 C11 1.453(4) . ?
N2 C10 1.454(4) . ?
N3 C12 1.149(4) . ?
N4 C16 1.366(4) . ?
N4 C19 1.445(4) . ?
N4 C20 1.455(4) . ?
C1 C2 1.430(4) . ?
C2 C3 1.381(4) . ?
C2 C12 1.436(4) . ?
C3 C4 1.459(4) . ?
C3 C13 1.468(4) . ?
C4 C5 1.401(4) . ?
C4 C9 1.402(4) . ?
C5 C6 1.375(4) . ?
C6 C7 1.410(4) . ?
C7 C8 1.413(4) . ?
C8 C9 1.376(4) . ?
C13 C14 1.397(4) . ?
C13 C18 1.402(4) . ?
C14 C15 1.379(4) . ?
C15 C16 1.408(4) . ?
C16 C17 1.405(4) . ?
C17 C18 1.377(4) . ?
C21 Cl2 1.707(4) . ?
C21 Cl1 1.746(4) . ?

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
C7 N2 C11 121.1(2) . . ?
C7 N2 C10 120.8(2) . . ?
C11 N2 C10 118.0(2) . . ?
C16 N4 C19 120.8(3) . . ?
C16 N4 C20 120.0(3) . . ?
C19 N4 C20 117.0(3) . . ?
N1 C1 C2 176.3(3) . . ?
C3 C2 C1 123.5(2) . . ?
C3 C2 C12 122.6(2) . . ?
C1 C2 C12 113.8(2) . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 C13 118.6(2) . . ?
C4 C3 C13 120.3(2) . . ?
C5 C4 C9 116.9(2) . . ?
C5 C4 C3 122.1(2) . . ?
C9 C4 C3 121.0(2) . . ?
C6 C5 C4 121.9(3) . . ?
C5 C6 C7 121.3(2) . . ?
N2 C7 C6 121.6(2) . . ?
N2 C7 C8 121.7(2) . . ?
C6 C7 C8 116.7(2) . . ?
C9 C8 C7 121.2(3) . . ?
C8 C9 C4 121.9(3) . . ?
N3 C12 C2 177.6(3) . . ?
C14 C13 C18 117.2(2) . . ?
C14 C13 C3 122.1(2) . . ?
C18 C13 C3 120.7(2) . . ?
C15 C14 C13 121.4(3) . . ?
C14 C15 C16 121.4(3) . . ?
N4 C16 C17 121.0(3) . . ?
N4 C16 C15 122.0(3) . . ?
C17 C16 C15 117.0(2) . . ?
C18 C17 C16 121.1(3) . . ?
C17 C18 C13 121.7(3) . . ?
Cl2 C21 Cl1 113.3(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        23.41
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.049

#===END
_chemical_name_common            
2-(bis(4-dimethylaminophenyl)methylene)malonitrile
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
_chemical_properties_physical    
'The crystals decay in few days owing to co-crystallized solvent loss'
_exptl_crystal_preparation       Luminescent
