# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1444520'
_audit_update_record             
;
2015-12-28 deposited with the CCDC.
2016-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            
2-(4-dicyanomethylenecyclohexa-2,5-dieny1idene)-imidazolidine.DMF
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N4, C3 H7 N O'
_chemical_formula_sum            'C15 H17 N5 O'
_chemical_formula_weight         283.34

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6328(5)
_cell_length_b                   11.2617(10)
_cell_length_c                   11.2686(10)
_cell_angle_alpha                86.4430(10)
_cell_angle_beta                 77.4390(10)
_cell_angle_gamma                85.4860(10)
_cell_volume                     694.81(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5189
_cell_measurement_theta_min      1.85
_cell_measurement_theta_max      26.380

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7425
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         26.38
_reflns_number_total             2813
_reflns_number_gt                2687
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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     
'calc w=1/[σ²(Fo²)+(0.0669P)²+0.1284P] where P=(Fo²+2Fc²)/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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2813
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
O17 O 1.19539(14) 0.18207(7) 0.39167(7) 0.0252(2) Uani 1 1 d . . .
N10 N 0.91728(17) 0.31452(8) 0.09963(8) 0.0207(2) Uani 1 1 d . . .
N20 N 0.80525(16) 0.24102(8) 0.48113(8) 0.0194(2) Uani 1 1 d . . .
N9 N 0.56925(16) 0.27102(8) 0.21657(8) 0.0203(2) Uani 1 1 d . . .
C3 C 0.82607(19) -0.10036(9) 0.23976(9) 0.0191(2) Uani 1 1 d . . .
N14 N 1.60140(17) -0.30695(8) 0.06884(9) 0.0238(2) Uani 1 1 d . . .
C12 C 1.40623(19) -0.28657(8) 0.12584(9) 0.0187(2) Uani 1 1 d . . .
N13 N 0.93617(17) -0.42261(8) 0.32098(9) 0.0254(2) Uani 1 1 d . . .
C6 C 1.12306(19) 0.07175(9) 0.11450(9) 0.0196(2) Uani 1 1 d . . .
C11 C 1.03943(19) -0.34724(9) 0.26195(9) 0.0193(2) Uani 1 1 d . . .
C2 C 0.73477(19) 0.01669(9) 0.23314(9) 0.0186(2) Uani 1 1 d . . .
C1 C 0.88201(18) 0.10522(9) 0.17017(9) 0.0173(2) Uani 1 1 d . . .
C8 C 1.16955(19) -0.25612(9) 0.19090(9) 0.0185(2) Uani 1 1 d . . .
C18 C 1.03003(19) 0.26067(10) 0.42113(9) 0.0215(2) Uani 1 1 d . . .
C21 C 0.7345(2) 0.12075(9) 0.51937(10) 0.0223(2) Uani 1 1 d . . .
C4 C 1.06862(18) -0.13455(9) 0.18382(9) 0.0170(2) Uani 1 1 d . . .
C15 C 0.53746(19) 0.40044(9) 0.19498(10) 0.0220(2) Uani 1 1 d . . .
C7 C 0.78847(18) 0.22874(9) 0.16263(9) 0.0173(2) Uani 1 1 d . . .
C5 C 1.21452(19) -0.04471(9) 0.12049(9) 0.0196(2) Uani 1 1 d . . .
C22 C 0.6264(2) 0.33937(10) 0.51892(10) 0.0239(2) Uani 1 1 d . . .
C16 C 0.76924(19) 0.42771(9) 0.09975(10) 0.0203(2) Uani 1 1 d . . .
H16A H 0.852(2) 0.4903(12) 0.1247(11) 0.021(3) Uiso 1 1 d . . .
H16B H 0.737(2) 0.4466(10) 0.0202(11) 0.016(3) Uiso 1 1 d . . .
H5 H 1.378(3) -0.0660(12) 0.0835(12) 0.023(3) Uiso 1 1 d . . .
H3 H 0.722(2) -0.1611(12) 0.2839(12) 0.022(3) Uiso 1 1 d . . .
H6 H 1.231(2) 0.1308(12) 0.0704(12) 0.025(3) Uiso 1 1 d . . .
H2 H 0.571(3) 0.0367(12) 0.2701(13) 0.027(3) Uiso 1 1 d . . .
H15A H 0.532(2) 0.4399(12) 0.2707(12) 0.025(3) Uiso 1 1 d . . .
H15B H 0.387(3) 0.4203(12) 0.1643(12) 0.029(3) Uiso 1 1 d . . .
H21A H 0.570(3) 0.1140(12) 0.5091(12) 0.025(3) Uiso 1 1 d . . .
H22A H 0.586(3) 0.3397(12) 0.6077(14) 0.031(3) Uiso 1 1 d . . .
H18 H 1.053(2) 0.3470(12) 0.3994(12) 0.022(3) Uiso 1 1 d . . .
H21C H 0.740(2) 0.1042(12) 0.6035(13) 0.027(3) Uiso 1 1 d . . .
H21B H 0.840(3) 0.0636(14) 0.4689(14) 0.037(4) Uiso 1 1 d . . .
H10 H 1.064(3) 0.3018(13) 0.0480(13) 0.029(3) Uiso 1 1 d . . .
H22B H 0.480(3) 0.3296(12) 0.4875(12) 0.026(3) Uiso 1 1 d . . .
H22C H 0.697(3) 0.4165(13) 0.4852(13) 0.029(3) Uiso 1 1 d . . .
H9 H 0.454(3) 0.2294(14) 0.2744(14) 0.038(4) Uiso 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
O17 C18 1.2383(14) . ?
N10 C7 1.3284(13) . ?
N10 C16 1.4673(13) . ?
N10 H10 0.909(16) . ?
N20 C18 1.3276(14) . ?
N20 C21 1.4549(14) . ?
N20 C22 1.4557(14) . ?
N9 C7 1.3183(13) . ?
N9 C15 1.4661(13) . ?
N9 H9 0.944(17) . ?
C3 C2 1.3803(14) . ?
C3 C4 1.4089(14) . ?
C3 H3 0.976(13) . ?
N14 C12 1.1598(14) . ?
C12 C8 1.4024(15) . ?
N13 C11 1.1578(14) . ?
C6 C5 1.3741(15) . ?
C6 C1 1.3991(14) . ?
C6 H6 0.974(14) . ?
C11 C8 1.4116(14) . ?
C2 C1 1.4042(14) . ?
C2 H2 0.940(15) . ?
C1 C7 1.4523(14) . ?
C8 C4 1.4448(14) . ?
C18 H18 0.999(14) . ?
C21 H21A 0.968(14) . ?
C21 H21C 0.962(14) . ?
C21 H21B 0.964(16) . ?
C4 C5 1.4122(14) . ?
C15 C16 1.5372(15) . ?
C15 H15A 0.980(13) . ?
C15 H15B 0.988(14) . ?
C5 H5 0.945(14) . ?
C22 H22A 0.976(15) . ?
C22 H22B 0.979(14) . ?
C22 H22C 1.001(14) . ?
C16 H16A 0.961(13) . ?
C16 H16B 0.960(12) . ?

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 N10 C16 111.29(9) . . ?
C7 N10 H10 124.4(9) . . ?
C16 N10 H10 122.7(9) . . ?
C18 N20 C21 121.09(9) . . ?
C18 N20 C22 121.18(9) . . ?
C21 N20 C22 117.57(9) . . ?
C7 N9 C15 111.50(9) . . ?
C7 N9 H9 126.2(10) . . ?
C15 N9 H9 121.3(10) . . ?
C2 C3 C4 121.20(9) . . ?
C2 C3 H3 120.0(8) . . ?
C4 C3 H3 118.8(8) . . ?
N14 C12 C8 176.87(11) . . ?
C5 C6 C1 121.17(10) . . ?
C5 C6 H6 118.2(8) . . ?
C1 C6 H6 120.6(8) . . ?
N13 C11 C8 178.85(11) . . ?
C3 C2 C1 120.70(9) . . ?
C3 C2 H2 119.4(8) . . ?
C1 C2 H2 119.9(8) . . ?
C6 C1 C2 118.34(9) . . ?
C6 C1 C7 120.37(9) . . ?
C2 C1 C7 121.29(9) . . ?
C12 C8 C11 117.74(9) . . ?
C12 C8 C4 119.67(9) . . ?
C11 C8 C4 122.59(9) . . ?
O17 C18 N20 124.88(10) . . ?
O17 C18 H18 122.4(8) . . ?
N20 C18 H18 112.7(8) . . ?
N20 C21 H21A 108.8(8) . . ?
N20 C21 H21C 110.4(8) . . ?
H21A C21 H21C 109.1(11) . . ?
N20 C21 H21B 110.1(9) . . ?
H21A C21 H21B 107.9(12) . . ?
H21C C21 H21B 110.4(12) . . ?
C3 C4 C5 117.53(9) . . ?
C3 C4 C8 122.26(9) . . ?
C5 C4 C8 120.20(9) . . ?
N9 C15 C16 102.59(8) . . ?
N9 C15 H15A 109.3(8) . . ?
C16 C15 H15A 111.0(8) . . ?
N9 C15 H15B 109.6(8) . . ?
C16 C15 H15B 112.7(8) . . ?
H15A C15 H15B 111.3(11) . . ?
N9 C7 N10 111.16(9) . . ?
N9 C7 C1 125.41(9) . . ?
N10 C7 C1 123.42(9) . . ?
C6 C5 C4 121.06(10) . . ?
C6 C5 H5 120.4(8) . . ?
C4 C5 H5 118.5(8) . . ?
N20 C22 H22A 109.2(8) . . ?
N20 C22 H22B 109.1(8) . . ?
H22A C22 H22B 110.4(11) . . ?
N20 C22 H22C 109.4(8) . . ?
H22A C22 H22C 109.3(11) . . ?
H22B C22 H22C 109.4(11) . . ?
N10 C16 C15 102.23(8) . . ?
N10 C16 H16A 110.0(8) . . ?
C15 C16 H16A 111.2(8) . . ?
N10 C16 H16B 109.9(7) . . ?
C15 C16 H16B 112.5(7) . . ?
H16A C16 H16B 110.6(10) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1444521'
_audit_update_record             
;
2015-12-28 deposited with the CCDC.
2016-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            
2-(4-dicyanomethylenecyclohexa-2,5-dieny1idene)-1-ethylimidazolidine.
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H30 N8 O'
_chemical_formula_weight         494.60

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   14.7692(12)
_cell_length_b                   7.3550(6)
_cell_length_c                   24.420(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.3880(10)
_cell_angle_gamma                90.00
_cell_volume                     2557.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7849
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      24.97

_exptl_crystal_description       flake
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23583
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.43
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4506
_reflns_number_gt                3828
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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     
'calc w=1/[σ²(Fo²)+(0.0416P)²+1.9125P] where P=(Fo²+2Fc²)/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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4506
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_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
N9 N 0.16252(14) 0.2508(3) 0.24828(7) 0.0200(4) Uani 1 1 d . . .
N5 N 0.30653(13) 0.3536(2) 0.27062(8) 0.0203(4) Uani 1 1 d . . .
C1 C 0.21512(15) 0.3204(3) 0.46176(9) 0.0166(5) Uani 1 1 d . . .
C2 C 0.22776(15) 0.3239(3) 0.34826(9) 0.0170(5) Uani 1 1 d . . .
C3 C 0.23291(15) 0.3114(3) 0.28939(9) 0.0178(5) Uani 1 1 d . . .
C4 C 0.12663(16) 0.3287(3) 0.53585(9) 0.0193(5) Uani 1 1 d . . .
C5 C 0.30663(15) 0.2875(3) 0.39319(9) 0.0180(5) Uani 1 1 d . . .
H5 H 0.3651 0.2626 0.3855 0.022 Uiso 1 1 calc R . .
N2 N 0.05715(13) 0.3387(3) 0.54909(8) 0.0264(5) Uani 1 1 d . . .
C6 C 0.13614(15) 0.3577(3) 0.41632(9) 0.0169(5) Uani 1 1 d . . .
H6 H 0.0776 0.3831 0.4240 0.020 Uiso 1 1 calc R . .
C7 C 0.14204(15) 0.3580(3) 0.36097(9) 0.0170(5) Uani 1 1 d . . .
H7 H 0.0874 0.3816 0.3310 0.020 Uiso 1 1 calc R . .
O1 O 0.46655(13) 0.9567(3) 0.38855(8) 0.0360(5) Uani 1 1 d . . .
N1 N 0.36290(13) 0.2636(3) 0.59844(8) 0.0264(5) Uani 1 1 d . . .
C8 C 0.18572(16) 0.2470(3) 0.19386(9) 0.0242(5) Uani 1 1 d . . .
H8A H 0.1452 0.3310 0.1663 0.029 Uiso 1 1 calc R . .
H8B H 0.1795 0.1229 0.1776 0.029 Uiso 1 1 calc R . .
C9 C 0.21104(15) 0.3132(3) 0.52000(9) 0.0180(5) Uani 1 1 d . . .
C10 C 0.28802(17) 0.3102(3) 0.20989(9) 0.0268(6) Uani 1 1 d . . .
H10A H 0.3302 0.2125 0.2035 0.032 Uiso 1 1 calc R . .
H10B H 0.2961 0.4187 0.1877 0.032 Uiso 1 1 calc R . .
C11 C 0.30065(15) 0.2875(3) 0.44807(9) 0.0176(5) Uani 1 1 d . . .
H11 H 0.3556 0.2646 0.4778 0.021 Uiso 1 1 calc R . .
C12 C 0.29318(15) 0.2845(3) 0.56391(9) 0.0183(5) Uani 1 1 d . . .
C13 C 0.48021(17) 0.3669(4) 0.30608(12) 0.0355(6) Uani 1 1 d . . .
H13A H 0.4804 0.2583 0.3294 0.053 Uiso 1 1 calc R . .
H13B H 0.5317 0.4476 0.3253 0.053 Uiso 1 1 calc R . .
H13C H 0.4885 0.3309 0.2691 0.053 Uiso 1 1 calc R . .
C14 C 0.38789(15) 0.4653(3) 0.29762(10) 0.0245(5) Uani 1 1 d . . .
H14A H 0.3817 0.5069 0.3350 0.029 Uiso 1 1 calc R . .
H14B H 0.3883 0.5744 0.2739 0.029 Uiso 1 1 calc R . .
N10 N 0.12125(13) 0.8107(3) 0.44827(7) 0.0193(4) Uani 1 1 d . . .
C15 C 0.19137(15) 0.7998(3) 0.55035(9) 0.0171(5) Uani 1 1 d . . .
N7 N 0.27445(12) 0.8249(2) 0.47429(7) 0.0186(4) Uani 1 1 d . . .
C16 C 0.19740(14) 0.8118(3) 0.49176(9) 0.0168(5) Uani 1 1 d . . .
C17 C 0.10155(15) 0.8456(3) 0.61845(9) 0.0186(5) Uani 1 1 d . . .
H17 H 0.0459 0.8887 0.6266 0.022 Uiso 1 1 calc R . .
C18 C 0.23702(16) 0.6718(3) 0.76150(9) 0.0202(5) Uani 1 1 d . . .
C19 C 0.25301(15) 0.7044(3) 0.64764(9) 0.0188(5) Uani 1 1 d . . .
H19 H 0.3021 0.6496 0.6760 0.023 Uiso 1 1 calc R . .
C20 C 0.26220(15) 0.7200(3) 0.59324(9) 0.0187(5) Uani 1 1 d . . .
H20 H 0.3174 0.6761 0.5847 0.022 Uiso 1 1 calc R . .
C21 C 0.11072(15) 0.8607(3) 0.56421(9) 0.0185(5) Uani 1 1 d . . .
H21 H 0.0613 0.9137 0.5356 0.022 Uiso 1 1 calc R . .
C22 C 0.16443(15) 0.7524(3) 0.71947(9) 0.0190(5) Uani 1 1 d . . .
C23 C 0.17248(15) 0.7679(3) 0.66215(9) 0.0178(5) Uani 1 1 d . . .
C24 C 0.08540(16) 0.8184(3) 0.73468(9) 0.0201(5) Uani 1 1 d . . .
N3 N 0.01980(14) 0.8759(3) 0.74603(8) 0.0264(5) Uani 1 1 d . . .
N4 N 0.29914(14) 0.6022(3) 0.79379(8) 0.0254(5) Uani 1 1 d . . .
C25 C 0.14586(15) 0.8339(3) 0.39437(9) 0.0211(5) Uani 1 1 d . . .
H25A H 0.1285 0.9565 0.3782 0.025 Uiso 1 1 calc R . .
H25B H 0.1149 0.7411 0.3663 0.025 Uiso 1 1 calc R . .
C26 C 0.25211(15) 0.8085(3) 0.41207(9) 0.0204(5) Uani 1 1 d . . .
H26A H 0.2701 0.6876 0.4006 0.025 Uiso 1 1 calc R . .
H26B H 0.2840 0.9040 0.3955 0.025 Uiso 1 1 calc R . .
C27 C 0.37150(15) 0.8565(3) 0.50734(10) 0.0209(5) Uani 1 1 d . . .
H27A H 0.3715 0.8974 0.5460 0.025 Uiso 1 1 calc R . .
H27B H 0.3989 0.9551 0.4892 0.025 Uiso 1 1 calc R . .
C28 C 0.43242(15) 0.6890(3) 0.51206(10) 0.0250(5) Uani 1 1 d . . .
H28A H 0.4049 0.5898 0.5291 0.037 Uiso 1 1 calc R . .
H28B H 0.4955 0.7160 0.5360 0.037 Uiso 1 1 calc R . .
H28C H 0.4363 0.6526 0.4741 0.037 Uiso 1 1 calc R . .
H41 H 0.1082(17) 0.202(3) 0.2530(9) 0.021(6) Uiso 1 1 d . . .
H40 H 0.0653(19) 0.767(4) 0.4503(11) 0.035(7) Uiso 1 1 d . . .
H43 H 0.423(2) 0.930(4) 0.3559(14) 0.060(10) Uiso 1 1 d . . .
H42 H 0.517(2) 0.883(5) 0.3869(14) 0.076(11) Uiso 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
N9 C3 1.317(3) . ?
N9 C8 1.458(3) . ?
N9 H41 0.91(2) . ?
N5 C3 1.324(3) . ?
N5 C14 1.461(3) . ?
N5 C10 1.470(3) . ?
C1 C6 1.407(3) . ?
C1 C11 1.411(3) . ?
C1 C9 1.440(3) . ?
C2 C5 1.398(3) . ?
C2 C7 1.404(3) . ?
C2 C3 1.462(3) . ?
C4 N2 1.157(3) . ?
C4 C9 1.405(3) . ?
C5 C11 1.366(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
O1 H43 0.90(3) . ?
O1 H42 0.93(4) . ?
N1 C12 1.155(3) . ?
C8 C10 1.529(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C12 1.406(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11 0.9500 . ?
C13 C14 1.509(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N10 C16 1.326(3) . ?
N10 C25 1.465(3) . ?
N10 H40 0.90(3) . ?
C15 C21 1.396(3) . ?
C15 C20 1.398(3) . ?
C15 C16 1.460(3) . ?
N7 C16 1.321(3) . ?
N7 C27 1.465(3) . ?
N7 C26 1.472(3) . ?
C17 C21 1.371(3) . ?
C17 C23 1.404(3) . ?
C17 H17 0.9500 . ?
C18 N4 1.158(3) . ?
C18 C22 1.404(3) . ?
C19 C20 1.376(3) . ?
C19 C23 1.408(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C24 1.402(3) . ?
C22 C23 1.441(3) . ?
C24 N3 1.156(3) . ?
C25 C26 1.525(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.512(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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
C3 N9 C8 111.87(19) . . ?
C3 N9 H41 125.3(14) . . ?
C8 N9 H41 122.4(14) . . ?
C3 N5 C14 128.92(19) . . ?
C3 N5 C10 110.40(18) . . ?
C14 N5 C10 119.21(18) . . ?
C6 C1 C11 116.98(19) . . ?
C6 C1 C9 122.87(19) . . ?
C11 C1 C9 120.15(19) . . ?
C5 C2 C7 118.25(19) . . ?
C5 C2 C3 120.64(19) . . ?
C7 C2 C3 120.91(19) . . ?
N9 C3 N5 111.72(19) . . ?
N9 C3 C2 122.3(2) . . ?
N5 C3 C2 126.0(2) . . ?
N2 C4 C9 179.0(3) . . ?
C11 C5 C2 120.8(2) . . ?
C11 C5 H5 119.6 . . ?
C2 C5 H5 119.6 . . ?
C7 C6 C1 121.3(2) . . ?
C7 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C6 C7 C2 120.8(2) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
H43 O1 H42 103(3) . . ?
N9 C8 C10 102.48(17) . . ?
N9 C8 H8A 111.3 . . ?
C10 C8 H8A 111.3 . . ?
N9 C8 H8B 111.3 . . ?
C10 C8 H8B 111.3 . . ?
H8A C8 H8B 109.2 . . ?
C4 C9 C12 116.84(19) . . ?
C4 C9 C1 122.81(19) . . ?
C12 C9 C1 120.33(19) . . ?
N5 C10 C8 103.35(17) . . ?
N5 C10 H10A 111.1 . . ?
C8 C10 H10A 111.1 . . ?
N5 C10 H10B 111.1 . . ?
C8 C10 H10B 111.1 . . ?
H10A C10 H10B 109.1 . . ?
C5 C11 C1 121.8(2) . . ?
C5 C11 H11 119.1 . . ?
C1 C11 H11 119.1 . . ?
N1 C12 C9 177.1(2) . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N5 C14 C13 113.4(2) . . ?
N5 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
N5 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 N10 C25 111.02(18) . . ?
C16 N10 H40 123.6(16) . . ?
C25 N10 H40 122.8(16) . . ?
C21 C15 C20 118.05(19) . . ?
C21 C15 C16 119.74(19) . . ?
C20 C15 C16 122.13(19) . . ?
C16 N7 C27 129.40(18) . . ?
C16 N7 C26 110.55(17) . . ?
C27 N7 C26 120.02(17) . . ?
N7 C16 N10 111.24(19) . . ?
N7 C16 C15 127.08(19) . . ?
N10 C16 C15 121.68(19) . . ?
C21 C17 C23 121.5(2) . . ?
C21 C17 H17 119.3 . . ?
C23 C17 H17 119.3 . . ?
N4 C18 C22 176.2(2) . . ?
C20 C19 C23 121.5(2) . . ?
C20 C19 H19 119.3 . . ?
C23 C19 H19 119.3 . . ?
C19 C20 C15 120.8(2) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
C17 C21 C15 121.2(2) . . ?
C17 C21 H21 119.4 . . ?
C15 C21 H21 119.4 . . ?
C24 C22 C18 118.73(19) . . ?
C24 C22 C23 121.27(19) . . ?
C18 C22 C23 119.99(19) . . ?
C17 C23 C19 116.99(19) . . ?
C17 C23 C22 122.25(19) . . ?
C19 C23 C22 120.77(19) . . ?
N3 C24 C22 178.2(2) . . ?
N10 C25 C26 102.30(17) . . ?
N10 C25 H25A 111.3 . . ?
C26 C25 H25A 111.3 . . ?
N10 C25 H25B 111.3 . . ?
C26 C25 H25B 111.3 . . ?
H25A C25 H25B 109.2 . . ?
N7 C26 C25 102.39(17) . . ?
N7 C26 H26A 111.3 . . ?
C25 C26 H26A 111.3 . . ?
N7 C26 H26B 111.3 . . ?
C25 C26 H26B 111.3 . . ?
H26A C26 H26B 109.2 . . ?
N7 C27 C28 112.86(18) . . ?
N7 C27 H27A 109.0 . . ?
C28 C27 H27A 109.0 . . ?
N7 C27 H27B 109.0 . . ?
C28 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 1444522'
_audit_update_record             
;
2015-12-28 deposited with the CCDC.
2016-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            
2-(4-dicyanomethylenecyclohexa-2,5-dieny1idene)-1,3-dimethylimidazolidine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N4'
_chemical_formula_weight         238.29

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   'P2(1)/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                   9.1349(6)
_cell_length_b                   11.5867(7)
_cell_length_c                   11.7632(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.4420(10)
_cell_angle_gamma                90.00
_cell_volume                     1231.57(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7902
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      24.98

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11502
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         24.98
_reflns_number_total             2165
_reflns_number_gt                2002
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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     
'calc w=1/[σ²(Fo²)+(0.0479P)²+0.3900P] where P=(Fo²+2Fc²)/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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2165
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
N2 N 0.23934(11) 0.21358(9) 0.79044(9) 0.0215(3) Uani 1 1 d . . .
N1 N 0.26794(11) 0.04120(9) 0.71994(9) 0.0213(2) Uani 1 1 d . . .
C1 C 0.81527(13) 0.29863(10) 0.52235(10) 0.0202(3) Uani 1 1 d . . .
C2 C 0.69024(13) 0.26317(10) 0.57535(10) 0.0202(3) Uani 1 1 d . . .
C3 C 0.81549(12) 0.40243(11) 0.45974(10) 0.0204(3) Uani 1 1 d . . .
N3 N 0.81570(12) 0.48854(9) 0.40982(9) 0.0257(3) Uani 1 1 d . . .
C4 C 0.69720(13) 0.16411(10) 0.64554(10) 0.0215(3) Uani 1 1 d . . .
H4 H 0.7866 0.1211 0.6589 0.026 Uiso 1 1 calc R . .
N4 N 1.04898(12) 0.17339(10) 0.54173(10) 0.0285(3) Uani 1 1 d . . .
C5 C 0.43662(13) 0.29041(10) 0.61190(10) 0.0219(3) Uani 1 1 d . . .
H5 H 0.3481 0.3347 0.6015 0.026 Uiso 1 1 calc R . .
C6 C 0.44515(13) 0.19014(10) 0.67891(10) 0.0202(3) Uani 1 1 d . . .
C7 C 0.57760(13) 0.12829(11) 0.69515(10) 0.0213(3) Uani 1 1 d . . .
H7 H 0.5853 0.0605 0.7411 0.026 Uiso 1 1 calc R . .
C8 C 0.94468(13) 0.23133(10) 0.53335(10) 0.0213(3) Uani 1 1 d . . .
C9 C 0.11733(13) 0.14766(11) 0.82710(11) 0.0234(3) Uani 1 1 d . . .
H9A H 0.0208 0.1851 0.8011 0.028 Uiso 1 1 calc R . .
H9B H 0.1307 0.1389 0.9117 0.028 Uiso 1 1 calc R . .
C10 C 0.55606(13) 0.32541(10) 0.56081(10) 0.0221(3) Uani 1 1 d . . .
H10 H 0.5476 0.3931 0.5147 0.026 Uiso 1 1 calc R . .
C11 C 0.12857(14) 0.03125(11) 0.76778(11) 0.0234(3) Uani 1 1 d . . .
H11A H 0.1328 -0.0331 0.8235 0.028 Uiso 1 1 calc R . .
H11B H 0.0437 0.0191 0.7063 0.028 Uiso 1 1 calc R . .
C12 C 0.31723(13) 0.14932(10) 0.72914(10) 0.0199(3) Uani 1 1 d . . .
C13 C 0.29705(15) -0.04280(11) 0.63447(11) 0.0273(3) Uani 1 1 d . . .
H13A H 0.2107 -0.0484 0.5745 0.041 Uiso 1 1 calc R . .
H13B H 0.3166 -0.1183 0.6712 0.041 Uiso 1 1 calc R . .
H13C H 0.3834 -0.0184 0.6000 0.041 Uiso 1 1 calc R . .
C14 C 0.27131(14) 0.33105(11) 0.83053(11) 0.0257(3) Uani 1 1 d . . .
H14A H 0.3772 0.3466 0.8333 0.039 Uiso 1 1 calc R . .
H14B H 0.2440 0.3401 0.9075 0.039 Uiso 1 1 calc R . .
H14C H 0.2142 0.3855 0.7777 0.039 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
N2 C12 1.3157(15) . ?
N2 C14 1.4560(16) . ?
N2 C9 1.4671(15) . ?
N1 C12 1.3304(16) . ?
N1 C13 1.4516(16) . ?
N1 C11 1.4700(15) . ?
C1 C8 1.4062(17) . ?
C1 C3 1.4104(17) . ?
C1 C2 1.4391(17) . ?
C2 C10 1.4107(17) . ?
C2 C4 1.4099(17) . ?
C3 N3 1.1579(16) . ?
C4 C7 1.3761(17) . ?
N4 C8 1.1577(16) . ?
C5 C10 1.3815(17) . ?
C5 C6 1.3997(17) . ?
C6 C7 1.3950(17) . ?
C6 C12 1.4633(16) . ?
C9 C11 1.5290(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
C12 N2 C14 127.41(10) . . ?
C12 N2 C9 111.21(10) . . ?
C14 N2 C9 121.09(10) . . ?
C12 N1 C13 126.41(10) . . ?
C12 N1 C11 110.15(10) . . ?
C13 N1 C11 118.01(10) . . ?
C8 C1 C3 117.08(11) . . ?
C8 C1 C2 120.78(11) . . ?
C3 C1 C2 122.12(11) . . ?
C10 C2 C4 116.80(11) . . ?
C10 C2 C1 122.15(11) . . ?
C4 C2 C1 121.04(11) . . ?
N3 C3 C1 179.00(13) . . ?
C7 C4 C2 121.57(11) . . ?
C10 C5 C6 120.43(11) . . ?
C7 C6 C5 118.62(11) . . ?
C7 C6 C12 120.44(11) . . ?
C5 C6 C12 120.93(11) . . ?
C4 C7 C6 120.90(11) . . ?
N4 C8 C1 178.22(13) . . ?
N2 C9 C11 102.72(9) . . ?
C5 C10 C2 121.65(11) . . ?
N1 C11 C9 103.04(9) . . ?
N2 C12 N1 111.94(11) . . ?
N2 C12 C6 124.52(11) . . ?
N1 C12 C6 123.53(11) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.041
