# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               J.Mater.Chem.

_journal_coden_Cambridge         1145

_publ_contact_author_name        'Yanlin Song'
_publ_contact_author_address     
;
Institute of Chemistry, Chinese Academy of Sciences
Beijing
100080
CHINA
;

_publ_contact_author_email       YLSONG@ICCAS.AC.CN

_publ_section_title              
;
A Non-planar Organic Molecule with Nonvolatile
Electrical Bistability for Nano-scale Data Storage
;
loop_
_publ_author_name
'Yanlin Song'
'Hongjun Gao'
'Junping Hu'
'Wenping Hu'
'Zhuoyu Ji'
;
Guiyuan Jiang
;
'Lei Jiang'
'Ying-Feng Li'
'Yongqiang Wen'
'Lian-Ming Yang'
;
Daoben Zhu
;

data_CPMAB
_database_code_depnum_ccdc_archive 'CCDC 624824'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"4-3, 4-dicyanophenoxy-4'-dimethylaminoazobenzene(CPMAB)"

_chemical_name_common            
"4-3, 4-dicyanophenoxy-4'-dimethylaminoazobenzene(CPMAB)"
_chemical_melting_point          471~473
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 N5 O'
_chemical_formula_weight         367.41

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   7.5300(15)
_cell_length_b                   12.173(2)
_cell_length_c                   40.996(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3757.8(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14285
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      25.02

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   
;
HIGASHI, T. (1995). Abscor-Empirical
Absorption
Correction based on Fourier Series
Approximation.Rigaku Corporation,Tokyo,
Japan.
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       Oscillation
_diffrn_detector_area_resol_mean '100x100 microns'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14285
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3010
_reflns_number_gt                1626
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
Molecular Structure Corporation (1994)
MSC/AFC Diffractometer Control Software
SC, 3200 Research Forest Drive, The
Woodlands, TX 77381, USA.
;
_computing_cell_refinement       
;
Molecular Structure Corporation (1994)
MSC/AFC Diffractometer Control Software
MSC, 3200 Research Forest Drive, The
Woodlands, TX 77381 USA.
;
_computing_data_reduction        
;
Sheldrick, G. M. (1998) SHELXS98, Program
for the Solution of Crystal Structure,
University of Gottingen, Germany.
;
_computing_structure_solution    
;
Sheldrick, G. M. (1998) SHELXS98, Program
for the Solution of Crystal Structure,
University of Gottingen, Germany.
;
_computing_structure_refinement  
;
Sheldrick, G. M. (1998) SHELXL98, Program
for the Refinement of Crystal Structure,
University of Gottingen, Germany.
;
_computing_molecular_graphics    
;
Interactive Molecular Graphics XP, Virsion
4.2 for MSDOS (1990), Siemens Analytical
X-ray Instruments Inc., Madison, Wisconsin,
USA.
;
_computing_publication_material  
;
Sheldrick, G. M. (1998) SHELXL98, Program
for the refinement of Crystal Structure,
University of Gottingen, Germany.
;

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0602P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   
;
hydrogen atoms are generated by HFIX
instructions.
;
_refine_ls_hydrogen_treatment    
;
hydrogen coordinates ride on the coordinates
of the previous atom, the isotropic U values
are 1.2 OR 1.5 time over the U values of the
previous atom.
;
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0079(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3010
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1331
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_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
O O 0.5819(3) 0.62049(14) 0.07760(4) 0.0673(6) Uani 1 1 d . . .
N1 N 0.6966(3) 0.59954(18) -0.05671(4) 0.0579(6) Uani 1 1 d . . .
N2 N 0.7941(3) 0.52016(19) -0.06556(5) 0.0614(6) Uani 1 1 d . . .
N3 N 0.8655(3) 0.4167(2) -0.19758(5) 0.0718(7) Uani 1 1 d . . .
N4 N 0.8135(4) 1.0006(2) 0.18817(6) 0.0886(9) Uani 1 1 d . . .
N5 N 0.4914(4) 0.7566(2) 0.21152(5) 0.0880(8) Uani 1 1 d . . .
C1 C 0.6272(3) 0.7046(2) 0.09794(5) 0.0505(6) Uani 1 1 d . . .
C2 C 0.7360(3) 0.7915(2) 0.08928(5) 0.0529(6) Uani 1 1 d . . .
H2 H 0.7784 0.7976 0.0681 0.064 Uiso 1 1 calc R . .
C3 C 0.7812(3) 0.8691(2) 0.11245(5) 0.0549(7) Uani 1 1 d . . .
H3 H 0.8538 0.9279 0.1067 0.066 Uiso 1 1 calc R . .
C4 C 0.7190(3) 0.8601(2) 0.14422(5) 0.0515(6) Uani 1 1 d . . .
C5 C 0.6087(3) 0.7725(2) 0.15253(5) 0.0516(6) Uani 1 1 d . . .
C6 C 0.5621(3) 0.6944(2) 0.12940(5) 0.0520(6) Uani 1 1 d . . .
H6 H 0.4883 0.6360 0.1349 0.062 Uiso 1 1 calc R . .
C7 C 0.6246(4) 0.6242(2) 0.04430(6) 0.0555(7) Uani 1 1 d . . .
C8 C 0.7355(4) 0.5438(2) 0.03264(6) 0.0640(7) Uani 1 1 d . . .
H8 H 0.7928 0.4963 0.0470 0.077 Uiso 1 1 calc R . .
C9 C 0.7609(4) 0.5342(2) -0.00045(6) 0.0614(7) Uani 1 1 d . . .
H9 H 0.8326 0.4782 -0.0085 0.074 Uiso 1 1 calc R . .
C10 C 0.6813(3) 0.6064(2) -0.02187(5) 0.0522(7) Uani 1 1 d . . .
C11 C 0.5764(4) 0.6894(2) -0.00950(6) 0.0676(8) Uani 1 1 d . . .
H11 H 0.5251 0.7402 -0.0236 0.081 Uiso 1 1 calc R . .
C12 C 0.5470(4) 0.6976(2) 0.02366(6) 0.0668(8) Uani 1 1 d . . .
H12 H 0.4746 0.7530 0.0319 0.080 Uiso 1 1 calc R . .
C13 C 0.8110(3) 0.5032(2) -0.09932(6) 0.0570(7) Uani 1 1 d . . .
C14 C 0.9031(4) 0.4100(2) -0.10864(6) 0.0688(8) Uani 1 1 d . . .
H14 H 0.9532 0.3656 -0.0926 0.083 Uiso 1 1 calc R . .
C15 C 0.9227(4) 0.3808(2) -0.14080(6) 0.0696(8) Uani 1 1 d . . .
H15 H 0.9854 0.3174 -0.1461 0.083 Uiso 1 1 calc R . .
C16 C 0.8498(3) 0.4450(2) -0.16574(6) 0.0577(7) Uani 1 1 d . . .
C17 C 0.7590(4) 0.5416(2) -0.15610(6) 0.0615(7) Uani 1 1 d . . .
H17 H 0.7099 0.5869 -0.1720 0.074 Uiso 1 1 calc R . .
C18 C 0.7419(3) 0.5699(2) -0.12381(6) 0.0568(7) Uani 1 1 d . . .
H18 H 0.6834 0.6346 -0.1182 0.068 Uiso 1 1 calc R . .
C19 C 0.7703(4) 0.9390(2) 0.16860(6) 0.0639(8) Uani 1 1 d . . .
C20 C 0.5431(4) 0.7622(2) 0.18548(6) 0.0625(7) Uani 1 1 d . . .
C21 C 0.7822(4) 0.4802(3) -0.22339(6) 0.0904(11) Uani 1 1 d . . .
H21A H 0.8086 0.4472 -0.2441 0.136 Uiso 1 1 calc R . .
H21B H 0.8271 0.5540 -0.2230 0.136 Uiso 1 1 calc R . .
H21C H 0.6560 0.4812 -0.2201 0.136 Uiso 1 1 calc R . .
C22 C 0.9637(5) 0.3193(3) -0.20733(6) 0.0933(11) Uani 1 1 d . . .
H22A H 0.9609 0.3124 -0.2307 0.140 Uiso 1 1 calc R . .
H22B H 0.9105 0.2555 -0.1976 0.140 Uiso 1 1 calc R . .
H22C H 1.0846 0.3256 -0.2002 0.140 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O 0.0909(15) 0.0630(12) 0.0479(10) -0.0120(9) 0.0135(9) -0.0186(10)
N1 0.0623(15) 0.0649(14) 0.0466(12) -0.0086(10) -0.0019(10) -0.0004(12)
N2 0.0634(15) 0.0729(15) 0.0481(12) -0.0086(11) 0.0016(10) 0.0017(13)
N3 0.0807(18) 0.0922(17) 0.0426(12) -0.0126(12) 0.0054(11) -0.0111(14)
N4 0.106(2) 0.0922(19) 0.0672(16) -0.0233(15) -0.0076(15) -0.0061(16)
N5 0.110(2) 0.104(2) 0.0501(14) 0.0020(13) 0.0182(14) 0.0092(17)
C1 0.0603(17) 0.0497(15) 0.0415(13) -0.0040(11) 0.0023(11) 0.0014(14)
C2 0.0658(17) 0.0547(15) 0.0384(12) 0.0017(12) 0.0065(11) 0.0005(13)
C3 0.0614(18) 0.0563(16) 0.0470(14) 0.0020(12) 0.0007(12) -0.0084(13)
C4 0.0574(17) 0.0555(16) 0.0416(13) -0.0031(12) -0.0030(11) 0.0001(13)
C5 0.0548(16) 0.0602(16) 0.0396(13) 0.0020(12) 0.0024(11) 0.0082(13)
C6 0.0551(16) 0.0562(15) 0.0448(13) -0.0022(12) 0.0055(11) -0.0034(13)
C7 0.0635(18) 0.0599(16) 0.0433(14) -0.0087(13) 0.0059(12) -0.0102(14)
C8 0.081(2) 0.0626(18) 0.0486(15) 0.0028(14) 0.0046(14) 0.0062(15)
C9 0.070(2) 0.0619(19) 0.0525(15) -0.0030(14) 0.0103(14) 0.0082(15)
C10 0.0548(17) 0.0582(17) 0.0435(13) -0.0067(12) -0.0018(11) -0.0034(13)
C11 0.077(2) 0.0725(18) 0.0537(16) -0.0116(14) -0.0115(14) 0.0156(16)
C12 0.0677(19) 0.0771(19) 0.0555(15) -0.0162(15) -0.0027(13) 0.0205(16)
C13 0.0579(18) 0.0715(18) 0.0414(13) -0.0043(13) 0.0006(12) -0.0034(14)
C14 0.073(2) 0.085(2) 0.0484(16) -0.0015(14) 0.0017(13) 0.0202(17)
C15 0.075(2) 0.082(2) 0.0515(16) -0.0054(15) 0.0067(14) 0.0073(17)
C16 0.0572(18) 0.0741(19) 0.0417(14) -0.0066(14) 0.0092(12) -0.0144(14)
C17 0.0623(18) 0.078(2) 0.0439(14) 0.0074(14) 0.0001(12) -0.0084(15)
C18 0.0530(16) 0.0626(17) 0.0549(15) -0.0020(13) 0.0049(12) -0.0018(13)
C19 0.071(2) 0.0675(18) 0.0528(15) -0.0031(15) -0.0010(14) -0.0011(15)
C20 0.0716(19) 0.0716(19) 0.0443(15) 0.0007(13) 0.0051(13) 0.0062(15)
C21 0.114(3) 0.110(3) 0.0465(15) -0.0021(17) -0.0044(17) -0.025(2)
C22 0.100(3) 0.115(3) 0.0653(19) -0.0302(19) 0.0163(17) -0.006(2)

_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
O C1 1.364(3) . ?
O C7 1.403(3) . ?
N1 N2 1.267(3) . ?
N1 C10 1.435(3) . ?
N2 C13 1.405(3) . ?
N3 C16 1.355(3) . ?
N3 C22 1.454(4) . ?
N3 C21 1.452(3) . ?
N4 C19 1.145(3) . ?
N5 C20 1.138(3) . ?
C1 C2 1.385(3) . ?
C1 C6 1.386(3) . ?
C2 C3 1.382(3) . ?
C3 C4 1.389(3) . ?
C4 C5 1.393(3) . ?
C4 C19 1.439(4) . ?
C5 C6 1.388(3) . ?
C5 C20 1.444(3) . ?
C7 C12 1.363(3) . ?
C7 C8 1.372(3) . ?
C8 C9 1.375(3) . ?
C9 C10 1.379(3) . ?
C10 C11 1.380(3) . ?
C11 C12 1.381(3) . ?
C13 C14 1.384(3) . ?
C13 C18 1.392(3) . ?
C14 C15 1.373(3) . ?
C15 C16 1.399(3) . ?
C16 C17 1.417(4) . ?
C17 C18 1.374(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
C1 O C7 120.90(18) . . ?
N2 N1 C10 112.1(2) . . ?
N1 N2 C13 116.6(2) . . ?
C16 N3 C22 121.1(2) . . ?
C16 N3 C21 122.0(3) . . ?
C22 N3 C21 116.9(2) . . ?
O C1 C2 124.4(2) . . ?
O C1 C6 114.4(2) . . ?
C2 C1 C6 121.1(2) . . ?
C3 C2 C1 119.5(2) . . ?
C2 C3 C4 120.5(2) . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 C19 120.5(2) . . ?
C5 C4 C19 120.1(2) . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 C20 119.5(2) . . ?
C4 C5 C20 119.9(2) . . ?
C1 C6 C5 119.0(2) . . ?
C12 C7 C8 120.8(2) . . ?
C12 C7 O 121.8(2) . . ?
C8 C7 O 117.1(2) . . ?
C7 C8 C9 119.3(2) . . ?
C8 C9 C10 120.9(2) . . ?
C9 C10 C11 118.8(2) . . ?
C9 C10 N1 124.2(2) . . ?
C11 C10 N1 117.0(2) . . ?
C12 C11 C10 120.4(2) . . ?
C7 C12 C11 119.7(2) . . ?
C14 C13 C18 117.8(2) . . ?
C14 C13 N2 116.0(2) . . ?
C18 C13 N2 126.2(2) . . ?
C15 C14 C13 122.1(2) . . ?
C14 C15 C16 121.0(3) . . ?
N3 C16 C15 121.9(3) . . ?
N3 C16 C17 121.4(2) . . ?
C15 C16 C17 116.7(2) . . ?
C18 C17 C16 121.5(2) . . ?
C17 C18 C13 120.9(3) . . ?
N4 C19 C4 178.8(3) . . ?
N5 C20 C5 178.4(3) . . ?

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
C10 N1 N2 C13 177.1(2) . . . . ?
C7 O C1 C2 -8.8(4) . . . . ?
C7 O C1 C6 174.3(2) . . . . ?
O C1 C2 C3 -176.4(2) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 C19 178.1(2) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C19 C4 C5 C6 -178.3(2) . . . . ?
C3 C4 C5 C20 -180.0(2) . . . . ?
C19 C4 C5 C20 1.2(4) . . . . ?
O C1 C6 C5 176.5(2) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C20 C5 C6 C1 -179.4(2) . . . . ?
C1 O C7 C12 -67.8(3) . . . . ?
C1 O C7 C8 118.3(3) . . . . ?
C12 C7 C8 C9 -3.4(4) . . . . ?
O C7 C8 C9 170.7(2) . . . . ?
C7 C8 C9 C10 2.2(4) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C8 C9 C10 N1 -177.8(2) . . . . ?
N2 N1 C10 C9 -1.0(3) . . . . ?
N2 N1 C10 C11 -179.3(2) . . . . ?
C9 C10 C11 C12 -2.2(4) . . . . ?
N1 C10 C11 C12 176.3(2) . . . . ?
C8 C7 C12 C11 1.7(4) . . . . ?
O C7 C12 C11 -172.0(2) . . . . ?
C10 C11 C12 C7 1.1(4) . . . . ?
N1 N2 C13 C14 -173.8(2) . . . . ?
N1 N2 C13 C18 5.1(4) . . . . ?
C18 C13 C14 C15 -2.0(4) . . . . ?
N2 C13 C14 C15 177.1(2) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C22 N3 C16 C15 -1.7(4) . . . . ?
C21 N3 C16 C15 176.8(3) . . . . ?
C22 N3 C16 C17 178.0(3) . . . . ?
C21 N3 C16 C17 -3.5(4) . . . . ?
C14 C15 C16 N3 -179.0(2) . . . . ?
C14 C15 C16 C17 1.3(4) . . . . ?
N3 C16 C17 C18 179.5(2) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C16 C17 C18 C13 -1.1(4) . . . . ?
C14 C13 C18 C17 2.5(4) . . . . ?
N2 C13 C18 C17 -176.5(2) . . . . ?
C3 C4 C19 N4 -96(15) . . . . ?
C5 C4 C19 N4 83(15) . . . . ?
C6 C5 C20 N5 -149(12) . . . . ?
C4 C5 C20 N5 32(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.909
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.909
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.037