# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2001


data_global

_database_code_CSD	163028

_journal_coden_Cambridge            207
_audit_creation_date                ?
_audit_creation_method              ?
_audit_update_record                ?
# PROCESSING SUMMARY (IUCr Office Use only) ##############
_journal_year                       ?
_journal_volume                     ?
_journal_issue                      ?
_journal_page_first                 ?
_journal_page_last                  ?
_journal_suppl_publ_number          ?
_journal_suppl_publ_pages           ?
# SUBMISSION DETAILS #####################################
_publ_contact_author         'Dr Alberto Flamini'
_publ_contact_author_address
;
Dr Alberto Flamini
Istituto di Chimica dei Materiali del CNR
Area della Ricerca di Roma/Montelibretti
Roma
Monterotondo Stazione
00016
ITALY
;
_publ_contact_letter
; Please consider this CIF submission as crystallographic data 
for publication in Perkin Trans. 1
;

_publ_contact_author_email   ' ALBERTO.FLAMINI@MLIB.CNR.IT '
_publ_requested_journal      ' Perkin Trans. 1 '
_publ_requested_category           ?
_publ_requested_coeditor_name      ?
#  TITLE  ################################################
_publ_section_title
;
5-amino-3-imino-1,2,6,7-tetracyano-3H-pyrrolizine: synthesis
of alkyl-imino derivatives. X-ray crystal and molecular structure
of the 6-hexenyl, and Langmuir-Blodgett film of the octyl and
octadecyl derivatives.
;
# AUTHOR LIST ############################################
loop_
_publ_author_name
'Capobianchi, Aldo'
'Fares, Vicenzo'
'Flamini, Alberto'
'Valentini, Veronica'

# TEXT ###################################################
_publ_section_abstract
;
;
_publ_section_comment
;
;
_publ_section_experimental
;
;
_publ_section_acknowledgements
;
;
_publ_section_references
;
;
_publ_section_figure_captions
;
;
_publ_section_table_legends
;
;
# DATA SECTION OF BLOCK ##################################
_chemical_name_systematic
;
5-amino-3-(6-hexenyl)-imino-1,2,6,7-tetracyano-pyrrolizine
;
_chemical_compound_source
;
;
_chemical_formula_iucr                      ?
_chemical_formula_analytical                ?
_chemical_formula_moiety                    ?
_chemical_formula_structural                ?
_chemical_formula_sum                'H13 C17 N7'
_chemical_formula_weight                 315.34

_chemical_melting_point                     ?
_computing_data_collection                  ?
_computing_cell_refinement                  ?
_computing_data_reduction                   ?
_computing_structure_solution  
'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)'
_computing_structure_refinement 
;
SHELXTL PC, Siemens Analytical X-Ray Instruments, Madison, WI, 1990
;
_computing_molecular_graphics  
;
SHELXTL PC, Siemens Analytical X-Ray Instruments, Madison, WI, 1990
;
_computing_publication_material            ?
_cell_length_a                            6.136
_cell_length_b                           30.470
_cell_length_c                            9.285
_cell_angle_alpha                        90.000
_cell_angle_beta                        102.810
_cell_angle_gamma                        90.000
_cell_volume                           1692.753
_cell_formula_units_Z                      4
_cell_measurement_radiation          'CuK\a'
_cell_measurement_wavelength            1.54180

_cell_measurement_temperature                   293
_cell_measurement_reflns_used                   25
_cell_measurement_theta_min                     40
_cell_measurement_theta_max                     55
_symmetry_cell_setting                 monoclinic
_symmetry_space_group_name_H-M       'P 21/n'
_symmetry_Int_Tables_number               14

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

_exptl_crystal_description    'platelets'
_exptl_crystal_colour         'bronze'
_exptl_crystal_size_max     0.6
_exptl_crystal_size_mid     0.2
_exptl_crystal_size_min     0.02
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn             1.238
_exptl_crystal_F_000                        656
_exptl_absorpt_coefficient_mu            ' 0.649 mm-1 '

_exptl_absorpt_correction_type  'semiempirical via \y scans (TEXSAN, 1985)'
_exptl_absorpt_correction_T_min             0.86
_exptl_absorpt_correction_T_max             1.00
_diffrn_ambient_temperature                    293
_diffrn_radiation_wavelength            1.54180
_diffrn_radiation_type               'CuK\a'
_diffrn_radiation_source             'Rigaku rotating anode'
_diffrn_radiation_monochromator      'graphite'

_diffrn_radiation_detector                      ?
_diffrn_measurement_device           'MSC-AFC5 diffractometer'
_diffrn_measurement_method           '\q-2\q scan'
_diffrn_standards_number                        3
_diffrn_standards_interval_count                147
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%                     'none'

loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
?  ?  ?
_diffrn_reflns_av_R_equivalents                 ?
_diffrn_reflns_av_sigmaI/netI                   ?
_diffrn_reflns_reduction_process                ?
_diffrn_reflns_number                        ?
_diffrn_reflns_theta_min                     5
_diffrn_reflns_theta_max                   124
_diffrn_reflns_limit_h_max                    7
_diffrn_reflns_limit_h_min                    0
_diffrn_reflns_limit_k_max                   34
_diffrn_reflns_limit_k_min                    0
_diffrn_reflns_limit_l_max                   10
_diffrn_reflns_limit_l_min                  -10
loop_
_atom_type_symbol               
_atom_type_number_in_cell       
_atom_type_description          
_atom_type_scat_dispersion_real 
_atom_type_scat_dispersion_imag 
_atom_type_scat_source          
'h   '   52 'Hydrogen    '  0.0000  0.0000 ' Int. Tab. C, 4.2.6.8, 6.1.1.4'
'c   '   68 'Carbon      '  0.0020  0.0020 ' Int. Tab. C, 4.2.6.8, 6.1.1.4'
'n   '   28 'Nitrogen    '  0.0040  0.0030 ' Int. Tab. C, 4.2.6.8, 6.1.1.4'

_atom_sites_solution_primary   ?
_atom_sites_solution_secondary                  ?
_atom_sites_solution_hydrogens                  ?
_reflns_number_total                       2660
_reflns_number_observed                    1492
_reflns_observed_criterion           'F > 6.0 sigma(F)'
_reflns_limit_h_max                           7
_reflns_limit_h_min                           0
_reflns_limit_k_max                          34
_reflns_limit_k_min                           0
_reflns_limit_l_max                          10
_reflns_limit_l_min                         -10
_reflns_d_resolution_high                 ?
_reflns_d_resolution_low                  ?

_refine_ls_structure_factor_coef          F
_refine_ls_extinction_method           'none'
_refine_ls_extinction_expression         ?
_refine_ls_extinction_coef               ?
_refine_ls_abs_structure_Flack           ?
_refine_ls_abs_structure_Rogers          ?
_refine_ls_abs_structure_details
;
;
_refine_ls_matrix_type               Full    
_refine_ls_hydrogen_treatment        'H atoms rigid to parent C atom'
_refine_ls_weighting_scheme          'W=1/(\s^2(Fo)+0.0005Fo^2)'
_refine_ls_number_reflns              1492
_refine_ls_number_parameters           217
_refine_ls_R_factor_all               0.1005
_refine_ls_R_factor_obs               0.0684
_refine_ls_wR_factor_all              0.1094
_refine_ls_wR_factor_obs              0.0982
_refine_ls_goodness_of_fit_all        ?
_refine_ls_goodness_of_fit_obs        2.20
_refine_ls_shift/esd_max              0.135
_refine_ls_shift/esd_mean             0.006
_refine_diff_density_max              0.35
_refine_diff_density_min              -0.32
_refine_diff_density_rms              ?

loop_
_atom_site_label  
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type

N(1)       0.3520(6)   0.0829(1)   0.3877(4)   1.000   0.060(1)    uani
C(2)       0.5427(8)   0.0599(2)   0.4382(5)   1.000   0.058(2)    uani
C(3)       0.6109(8)   0.0451(1)   0.3101(5)   1.000   0.057(2)    uani
C(4)       0.4524(7)   0.0608(2)   0.1839(5)   1.000   0.055(2)    uani
C(5)       0.2931(7)   0.0841(2)   0.2343(5)   1.000   0.058(2)    uani
C(6)       0.0953(8)   0.1095(2)   0.1976(5)   1.000   0.062(2)    uani
C(7)       0.0373(8)   0.1239(2)   0.3254(6)   1.000   0.063(2)    uani
N(8)       0.6294(7)   0.0545(1)   0.5806(4)   1.000   0.068(2)    uani
H(81)      0.7570(7)   0.0392(1)   0.6107(4)   1.000   0.080       uiso
H(82)      0.5606(7)   0.0663(1)   0.6476(4)   1.000   0.080       uiso
C(9)       0.8067(9)   0.0205(2)   0.3128(5)   1.000   0.062(2)    uani
C(10)      0.4641(8)   0.0549(2)   0.0338(6)   1.000   0.061(2)    uani
C(11)     -0.0311(8)   0.1180(2)   0.0534(6)   1.000   0.071(2)    uani
C(12)     -0.1611(9)   0.1477(2)   0.3301(6)   1.000   0.075(2)    uani
C(13)      0.2062(8)   0.1081(2)   0.4553(6)   1.000   0.064(2)    uani
N(14)      0.2470(7)   0.1119(1)   0.5930(5)   1.000   0.074(2)    uani
N(15)      0.9700(8)   0.0018(2)   0.3167(5)   1.000   0.080(2)    uani
N(16)      0.4777(8)   0.0508(2)  -0.0855(5)   1.000   0.082(2)    uani
N(17)     -0.1379(9)   0.1247(2)  -0.0612(6)   1.000   0.106(2)    uani
N(18)     -0.3265(8)   0.1647(2)   0.3291(6)   1.000   0.100(2)    uani
C(19)      0.1129(9)   0.1397(2)   0.6650(6)   1.000   0.098(3)    uani
H(191)     0.0195(9)   0.1224(2)   0.7135(6)   1.000   0.080       uiso
H(192)     0.0189(9)   0.1578(2)   0.5922(6)   1.000   0.080       uiso
C(20)      0.260(1)    0.1697(2)   0.7737(6)   1.000   0.090(3)    uani
H(201)     0.363(1)    0.1511(2)   0.8396(6)   1.000   0.080       uiso
H(202)     0.176(1)    0.1860(2)   0.8315(6)   1.000   0.080       uiso
C(21)      0.400(1)    0.2008(2)   0.7039(7)   1.000   0.109(3)    uani
H(211)     0.299(1)    0.2192(2)   0.6355(7)   1.000   0.080       uiso
H(212)     0.493(1)    0.1850(2)   0.6508(7)   1.000   0.080       uiso
C(22)      0.543(1)    0.2310(2)   0.8128(9)   1.000   0.133(4)    uani
H(221)     0.624(1)    0.2119(2)   0.8881(9)   1.000   0.080       uiso
H(222)     0.447(1)    0.2490(2)   0.8568(9)   1.000   0.080       uiso
C(23)      0.711(1)    0.2603(3)   0.761(1)    1.000   0.130(4)    uani
H(23)      0.811(1)    0.2763(3)   0.837(1)    1.000   0.080       uiso
C(24)      0.736(2)    0.2667(3)   0.644(1)    1.000   0.157(5)    uani
H(241)     0.815(2)    0.2475(3)   0.592(1)    1.000   0.080       uiso
H(242)     0.643(2)    0.2861(3)   0.575(1)    1.000   0.080       uiso

loop_
_atom_site_aniso_label  
_atom_site_aniso_U_11   
_atom_site_aniso_U_12   
_atom_site_aniso_U_13   
_atom_site_aniso_U_22   
_atom_site_aniso_U_23   
_atom_site_aniso_U_33   

N(1)      0.057(2)   0.007(2)   0.012(2)   0.067(2)   0.001(2)   0.055(2)  
C(2)      0.055(3)   0.004(2)   0.011(2)   0.056(3)   0.004(2)   0.061(3)  
C(3)      0.054(3)   0.003(2)   0.016(2)   0.054(2)  -0.001(2)   0.064(3)  
C(4)      0.050(3)  -0.003(2)   0.006(2)   0.061(3)   0.001(2)   0.052(3)  
C(5)      0.050(3)   0.001(2)   0.008(2)   0.067(3)   0.003(2)   0.054(3)  
C(6)      0.050(3)  -0.002(2)   0.013(2)   0.069(3)   0.015(3)   0.067(3)  
C(7)      0.048(3)   0.001(2)   0.015(2)   0.062(3)   0.007(3)   0.078(3)  
N(8)      0.068(3)   0.015(2)   0.006(2)   0.083(3)  -0.001(2)   0.051(2)  
C(9)      0.065(3)   0.002(3)   0.007(2)   0.069(3)  -0.003(2)   0.051(3)  
C(10)     0.059(3)   0.006(2)   0.014(2)   0.058(3)   0.003(3)   0.067(3)  
C(11)     0.050(3)   0.003(3)   0.009(3)   0.090(4)   0.016(3)   0.072(3)  
C(12)     0.061(3)  -0.001(3)   0.015(3)   0.075(4)  -0.001(3)   0.088(4)  
C(13)     0.058(3)  -0.002(2)   0.020(3)   0.067(3)  -0.006(3)   0.070(3)  
N(14)     0.069(3)   0.002(2)   0.019(2)   0.094(3)  -0.009(2)   0.061(3)  
N(15)     0.069(3)   0.018(3)   0.014(2)   0.091(3)  -0.003(3)   0.078(3)  
N(16)     0.104(4)   0.001(3)   0.019(3)   0.080(3)  -0.001(3)   0.062(3)  
N(17)     0.072(3)   0.005(3)   0.010(3)   0.151(5)   0.028(3)   0.090(4)  
N(18)     0.070(3)   0.022(3)   0.021(3)   0.102(4)  -0.002(3)   0.127(4)  
C(19)     0.076(4)   0.011(4)   0.032(3)   0.149(6)  -0.019(4)   0.075(3)  
C(20)     0.102(4)   0.001(4)   0.041(3)   0.089(4)  -0.013(3)   0.087(4)  
C(21)     0.124(5)   0.006(4)   0.046(4)   0.109(5)  -0.003(4)   0.105(5)  
C(22)     0.165(7)  -0.012(5)   0.084(6)   0.091(5)  -0.007(5)   0.165(7)  
C(23)     0.159(8)  -0.021(5)   0.031(6)   0.108(6)  -0.010(5)   0.124(6)  
C(24)     0.23(1)    0.041(7)   0.052(7)   0.149(8)   0.019(6)   0.095(5)  

# GEOMETRY ###############################################


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N(1)      C(2)        1.355(6)         . .   yes
N(1)      C(5)        1.390(6)         . .   yes
N(1)      C(13)       1.426(6)         . .   yes
C(2)      C(3)        1.420(6)         . .   yes
C(2)      N(8)        1.321(7)         . .   yes
C(3)      C(4)        1.429(7)         . .   yes
C(3)      C(9)        1.411(7)         . .   yes
C(4)      C(5)        1.372(6)         . .   yes
C(4)      C(10)       1.423(7)         . .   yes
C(5)      C(6)        1.415(7)         . .   yes
C(6)      C(7)        1.383(7)         . .   yes
C(6)      C(11)       1.414(8)         . .   yes
C(7)      C(12)       1.427(7)         . .   yes
C(7)      C(13)       1.485(8)         . .   yes
N(8)      H(81)       0.901(6)         . .   yes
N(8)      H(82)       0.901(5)         . .   yes
C(9)      N(15)       1.147(7)         . .   yes
C(10)     N(16)       1.136(7)         . .   yes
C(11)     N(17)       1.138(9)         . .   yes
C(12)     N(18)       1.137(8)         . .   yes
C(13)     N(14)       1.252(7)         . .   yes
N(14)     C(19)       1.443(7)         . .   yes
C(19)     H(191)      0.961(8)         . .   yes
C(19)     H(192)      0.961(9)         . .   yes
C(19)     C(20)       1.507(9)         . .   yes
C(20)     H(201)      0.961(9)         . .   yes
C(20)     H(202)      0.961(8)         . .   yes
C(20)     C(21)       1.515(9)         . .   yes
C(21)     H(211)      0.96(1)          . .   yes
C(21)     H(212)      0.961(9)         . .   yes
C(21)     C(22)       1.50(1)          . .   yes
C(22)     H(221)      0.96(1)          . .   yes
C(22)     H(222)      0.96(1)          . .   yes
C(22)     C(23)       1.52(1)          . .   yes
C(23)     H(23)       0.96(1)          . .   yes
C(23)     C(24)       1.15(1)          . .   yes
C(24)     H(241)      0.96(1)          . .   yes
C(24)     H(242)      0.96(1)          . .   yes


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_2  
_geom_angle_site_symmetry_3  
_geom_angle_publ_flag
C(5)      N(1)      C(2)     112.2(4)  . . .   yes
C(13)     N(1)      C(2)     134.7(4)  . . .   yes
C(13)     N(1)      C(5)     113.0(4)  . . .   yes
C(3)      C(2)      N(1)     105.4(4)  . . .   yes
N(8)      C(2)      N(1)     122.4(4)  . . .   yes
N(8)      C(2)      C(3)     132.2(5)  . . .   yes
C(2)      C(3)      C(9)     124.2(5)  . . .   yes
C(4)      C(3)      C(9)     127.9(4)  . . .   yes
C(4)      C(3)      C(2)     107.9(4)  . . .   yes
C(3)      C(4)      C(5)     107.5(4)  . . .   yes
C(10)     C(4)      C(5)     126.4(5)  . . .   yes
C(10)     C(4)      C(3)     126.0(4)  . . .   yes
C(4)      C(5)      C(6)     147.0(5)  . . .   yes
N(1)      C(5)      C(6)     106.0(4)  . . .   yes
N(1)      C(5)      C(4)     107.0(4)  . . .   yes
C(7)      C(6)      C(11)    124.3(5)  . . .   yes
C(5)      C(6)      C(11)    126.1(4)  . . .   yes
C(5)      C(6)      C(7)     109.6(5)  . . .   yes
C(13)     C(7)      C(12)    125.9(5)  . . .   yes
C(6)      C(7)      C(12)    124.8(5)  . . .   yes
C(6)      C(7)      C(13)    109.2(4)  . . .   yes
H(82)     N(8)      C(2)     119.7(5)  . . .   yes
H(81)     N(8)      C(2)     120.3(4)  . . .   yes
H(81)     N(8)      H(82)    120.0(6)  . . .   yes
C(3)      C(9)      N(15)    177.6(6)  . . .   yes
N(16)     C(10)     C(4)     178.5(5)  . . .   yes
N(17)     C(11)     C(6)     178.1(5)  . . .   yes
N(18)     C(12)     C(7)     175.7(6)  . . .   yes
C(7)      C(13)     N(1)     102.1(4)  . . .   yes
N(14)     C(13)     N(1)     119.8(5)  . . .   yes
N(14)     C(13)     C(7)     138.1(5)  . . .   yes
C(13)     N(14)     C(19)    121.5(5)  . . .   yes
H(191)    C(19)     N(14)    110.9(7)  . . .   yes
H(192)    C(19)     N(14)    109.0(6)  . . .   yes
H(192)    C(19)     H(191)   108.6(8)  . . .   yes
C(20)     C(19)     N(14)    110.3(5)  . . .   yes
C(20)     C(19)     H(191)   110.6(6)  . . .   yes
C(20)     C(19)     H(192)   107.4(7)  . . .   yes
H(201)    C(20)     C(19)    106.2(6)  . . .   yes
H(202)    C(20)     C(19)    111.7(7)  . . .   yes
H(202)    C(20)     H(201)   108.0(7)  . . .   yes
C(21)     C(20)     C(19)    113.9(5)  . . .   yes
C(21)     C(20)     H(201)   106.8(7)  . . .   yes
C(21)     C(20)     H(202)   110.0(6)  . . .   yes
H(211)    C(21)     C(20)    107.8(8)  . . .   yes
H(212)    C(21)     C(20)    111.2(7)  . . .   yes
H(212)    C(21)     H(211)   108.6(9)  . . .   yes
C(22)     C(21)     C(20)    113.4(6)  . . .   yes
C(22)     C(21)     H(211)   106.4(8)  . . .   yes
C(22)     C(21)     H(212)   109.1(8)  . . .   yes
H(221)    C(22)     C(21)    104.4(8)  . . .   yes
H(222)    C(22)     C(21)    108.2(9)  . . .   yes
H(222)    C(22)     H(221)   107(1)    . . .   yes
C(23)     C(22)     C(21)    119.1(7)  . . .   yes
C(23)     C(22)     H(221)   108.0(9)  . . .   yes
C(23)     C(22)     H(222)   108.8(8)  . . .   yes
H(23)     C(23)     C(22)    116(1)    . . .   yes
C(24)     C(23)     C(22)    129(1)    . . .   yes
C(24)     C(23)     H(23)    114(1)    . . .   yes
H(241)    C(24)     C(23)    124(1)    . . .   yes
H(242)    C(24)     C(23)    123(1)    . . .   yes
H(242)    C(24)     H(241)   109(1)    . . .   yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag

?  ? ?  ?  ?  .  .  .  .   ?

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag

?  ? ?  .  .  ?