# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is © The Royal Society of Chemistry 2002

data_global

_journal_coden_Cambridge      1145

_publ_requested_journal       'J. Material Chemistry'

loop_
_publ_author_name
'Chen, Y.'
'Harrison, W.T.'
'Imrie, C.'
'Ryder, Karl'


_publ_contact_author_name     	'Karl Ryder'  

_publ_contact_author_address 
;
Faculty of Applied Sciences, School of Pharm & Pharm Sci
De Monfort University,
Leicester
LE1 9BH
UNITED KINGDOM
;
  
  
_publ_contact_author_email       'kryder@dmu.ac.uk'

_publ_section_title		
;
Pyrrole and Polypyrrole-Based Liquid Crystals Containing Azobenzene
Mesogenic Groups
;

data_y609-3CN     
_database_code_CSD                  169300

#
# CIF file for compound "3-CN" (C20H18N4O)
# To accompany revised
# submission b105976a to J. Mater. Chem.
#

_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
'C20 H18 N4 O' 
_chemical_formula_weight          330.38 

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' 
'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' 
'H'  'H'   0.0000   0.0000 
'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                    9.5009(6) 
_cell_length_b                    13.9016(9) 
_cell_length_c                    14.6728(10) 
_cell_angle_alpha                 66.442(2) 
_cell_angle_beta                  81.618(2) 
_cell_angle_gamma                 81.938(2) 
_cell_volume                      1750.3(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     6565 
_cell_measurement_theta_min       3.20 
_cell_measurement_theta_max       28.59 

_exptl_crystal_description        plate 
_exptl_crystal_colour             orange 
_exptl_crystal_size_max           0.24 
_exptl_crystal_size_mid           0.24 
_exptl_crystal_size_min           0.02 

_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.254 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              696 
_exptl_absorpt_coefficient_mu     0.080 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.981 
_exptl_absorpt_correction_T_max   0.998 
_exptl_absorpt_process_details    'SADABS (Bruker, 1999)' 

_exptl_special_details 
; 
? 
; 


_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.69230 
_diffrn_radiation_type            synchrotron 
_diffrn_radiation_source          'Daresbury SRS station 9.8' 
_diffrn_radiation_monochromator   'silicon 111' 
_diffrn_measurement_device_type   'Bruker SMART CCD' 
_diffrn_measurement_method        \w 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         0 

_diffrn_reflns_number             12705 
_diffrn_reflns_av_R_equivalents   0.0187 
_diffrn_reflns_av_sigmaI/netI     0.0279 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -16 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        17 
_diffrn_reflns_theta_min          1.69 
_diffrn_reflns_theta_max          24.00 
_reflns_number_total              5899 
_reflns_number_gt                 4086 
_reflns_threshold_expression      'I>2\s(I)' 

_computing_data_collection        'SMART (Bruker, 1999)'  
_computing_cell_refinement        'SMART (Bruker, 1999)'   
_computing_data_reduction         'SMART (Bruker, 1999)'  
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)' 
_computing_publication_material   'SHELXL-97 (Sheldrick, 1997)' 

_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^)+(0.1573P)^2^+0.1855P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          5899 
_refine_ls_number_parameters      449 
_refine_ls_number_restraints      4 
_refine_ls_R_factor_all           0.100 
_refine_ls_R_factor_gt            0.079 
_refine_ls_wR_factor_ref          0.258 
_refine_ls_wR_factor_gt           0.240 
_refine_ls_goodness_of_fit_ref    1.11 
_refine_ls_restrained_S_all       1.11 
_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 
O1 O 0.0235(2) 0.23962(14) 0.14866(14) 0.0772(6) Uani 1 1 d . . . 
N1 N 0.7643(3) 1.0284(2) -0.36167(19) 0.0939(8) Uani 1 1 d . . . 
N2 N 0.4061(2) 0.59539(16) -0.11315(15) 0.0622(5) Uani 1 1 d . . . 
N3 N 0.3152(2) 0.59635(15) -0.04216(15) 0.0602(5) Uani 1 1 d . . . 
N4 N -0.2173(3) -0.03365(18) 0.41271(17) 0.0769(6) Uani 1 1 d . . . 
C1 C 0.7040(3) 0.9559(2) -0.3178(2) 0.0719(7) Uani 1 1 d . . . 
C2 C 0.6282(3) 0.86410(19) -0.26300(17) 0.0599(6) Uani 1 1 d . . . 
C3 C 0.6586(3) 0.7764(2) -0.28656(19) 0.0693(7) Uani 1 1 d . . . 
H31 H 0.7297 0.7761 -0.3372 0.083 Uiso 1 1 calc R . . 
C4 C 0.5845(3) 0.6899(2) -0.23569(19) 0.0692(7) Uani 1 1 d . . . 
H41 H 0.6057 0.6310 -0.2520 0.083 Uiso 1 1 calc R . . 
C5 C 0.4775(2) 0.68887(18) -0.15972(17) 0.0560(6) Uani 1 1 d . . . 
C6 C 0.4465(3) 0.77811(18) -0.13615(17) 0.0609(6) Uani 1 1 d . . . 
H61 H 0.3746 0.7786 -0.0860 0.073 Uiso 1 1 calc R . . 
C7 C 0.5212(3) 0.86459(19) -0.18638(18) 0.0659(7) Uani 1 1 d . . . 
H71 H 0.5011 0.9234 -0.1698 0.079 Uiso 1 1 calc R . . 
C8 C 0.2415(2) 0.50436(17) 0.00392(17) 0.0558(6) Uani 1 1 d . . . 
C9 C 0.2606(3) 0.42055(19) -0.02722(19) 0.0662(7) Uani 1 1 d . . . 
H91 H 0.3250 0.4233 -0.0822 0.079 Uiso 1 1 calc R . . 
C10 C 0.1859(3) 0.3349(2) 0.0220(2) 0.0705(7) Uani 1 1 d . . . 
H101 H 0.1988 0.2795 0.0005 0.085 Uiso 1 1 calc R . . 
C11 C 0.0898(3) 0.33025(19) 0.10497(18) 0.0610(6) Uani 1 1 d . . . 
C12 C 0.0692(3) 0.4132(2) 0.13586(19) 0.0681(7) Uani 1 1 d . . . 
H121 H 0.0046 0.4106 0.1907 0.082 Uiso 1 1 calc R . . 
C13 C 0.1449(3) 0.49981(19) 0.08511(18) 0.0651(7) Uani 1 1 d . . . 
H131 H 0.1308 0.5559 0.1057 0.078 Uiso 1 1 calc R . . 
C14 C -0.0632(3) 0.2212(2) 0.2408(2) 0.0745(7) Uani 1 1 d . . . 
H141 H -0.1458 0.2726 0.2315 0.089 Uiso 1 1 calc R . . 
H142 H -0.0092 0.2259 0.2900 0.089 Uiso 1 1 calc R . . 
C15 C -0.1092(3) 0.1108(2) 0.2747(2) 0.0756(8) Uani 1 1 d . . . 
H151 H -0.1778 0.1112 0.2315 0.091 Uiso 1 1 calc R . . 
H152 H -0.0268 0.0634 0.2680 0.091 Uiso 1 1 calc R . . 
C16 C -0.1738(4) 0.0711(2) 0.3792(2) 0.1001(11) Uani 1 1 d . . . 
H161 H -0.1053 0.0713 0.4220 0.120 Uiso 1 1 calc R . . 
H162 H -0.2564 0.1185 0.3855 0.120 Uiso 1 1 calc R . . 
C17 C -0.3479(4) -0.0638(4) 0.4225(3) 0.1185(14) Uani 1 1 d . . . 
H171 H -0.4324 -0.0202 0.4098 0.142 Uiso 1 1 calc R . . 
C18 C -0.3333(6) -0.1713(4) 0.4551(3) 0.1259(17) Uani 1 1 d . . . 
H181 H -0.4066 -0.2138 0.4663 0.151 Uiso 1 1 calc R . . 
C19 C -0.1979(6) -0.2048(3) 0.4678(3) 0.1121(13) Uani 1 1 d . . . 
H191 H -0.1599 -0.2747 0.4923 0.135 Uiso 1 1 calc R . . 
C20 C -0.1272(4) -0.1225(2) 0.4400(2) 0.0925(9) Uani 1 1 d . . . 
H201 H -0.0287 -0.1245 0.4390 0.111 Uiso 1 1 calc R . . 
O2 O -0.0097(2) 0.76169(14) 0.14262(14) 0.0795(6) Uani 1 1 d . . . 
N5 N 0.7980(3) 1.5117(2) -0.3546(2) 0.1073(10) Uani 1 1 d . . . 
N6 N 0.3882(2) 1.10488(15) -0.12378(15) 0.0617(5) Uani 1 1 d . . . 
N7 N 0.3368(2) 1.08876(15) -0.03607(15) 0.0601(5) Uani 1 1 d . . . 
N8 N -0.2334(3) 0.47399(19) 0.3988(2) 0.0877(7) Uani 1 1 d D . . 
C21 C 0.7314(3) 1.4421(2) -0.3133(2) 0.0802(8) Uani 1 1 d . . . 
C22 C 0.6469(3) 1.35491(19) -0.26261(19) 0.0653(7) Uani 1 1 d . . . 
C23 C 0.5967(3) 1.3282(2) -0.16227(19) 0.0688(7) Uani 1 1 d . . . 
H231 H 0.6209 1.3657 -0.1275 0.083 Uiso 1 1 calc R . . 
C24 C 0.5122(3) 1.2473(2) -0.11504(18) 0.0651(7) Uani 1 1 d . . . 
H241 H 0.4780 1.2305 -0.0483 0.078 Uiso 1 1 calc R . . 
C25 C 0.4768(3) 1.18963(18) -0.16566(17) 0.0570(6) Uani 1 1 d . . . 
C26 C 0.5296(3) 1.2148(2) -0.26471(19) 0.0777(8) Uani 1 1 d . . . 
H261 H 0.5078 1.1759 -0.2989 0.093 Uiso 1 1 calc R . . 
C27 C 0.6136(3) 1.2966(2) -0.3127(2) 0.0813(8) Uani 1 1 d . . . 
H271 H 0.6485 1.3130 -0.3793 0.098 Uiso 1 1 calc R . . 
C28 C 0.2470(2) 1.00574(17) 0.00663(17) 0.0556(6) Uani 1 1 d . . . 
C29 C 0.1997(3) 0.97841(19) 0.10631(18) 0.0634(6) Uani 1 1 d . . . 
H291 H 0.2265 1.0153 0.1408 0.076 Uiso 1 1 calc R . . 
C30 C 0.1135(3) 0.89759(19) 0.15574(19) 0.0645(6) Uani 1 1 d . . . 
H301 H 0.0829 0.8794 0.2232 0.077 Uiso 1 1 calc R . . 
C31 C 0.0729(3) 0.84367(18) 0.10373(19) 0.0616(6) Uani 1 1 d . . . 
C32 C 0.1178(3) 0.87212(19) 0.00257(19) 0.0656(7) Uani 1 1 d . . . 
H321 H 0.0894 0.8364 -0.0324 0.079 Uiso 1 1 calc R . . 
C33 C 0.2034(3) 0.95217(18) -0.04537(18) 0.0602(6) Uani 1 1 d . . . 
H331 H 0.2328 0.9711 -0.1131 0.072 Uiso 1 1 calc R . . 
C34 C -0.0671(3) 0.7284(2) 0.2442(2) 0.0745(7) Uani 1 1 d . B . 
H341 H -0.1380 0.7817 0.2540 0.089 Uiso 1 1 calc R . . 
H342 H 0.0078 0.7153 0.2872 0.089 Uiso 1 1 calc R . . 
C35 C -0.1349(3) 0.6277(2) 0.2670(2) 0.0830(8) Uani 1 1 d . . . 
H351 H -0.2139 0.6436 0.2267 0.100 Uiso 1 1 calc R B . 
H352 H -0.0651 0.5787 0.2488 0.100 Uiso 1 1 calc R . . 
C36 C -0.1880(4) 0.5772(2) 0.3745(2) 0.0939(10) Uani 1 1 d . B . 
H361 H -0.1126 0.5707 0.4152 0.113 Uiso 1 1 calc R . . 
H362 H -0.2676 0.6217 0.3902 0.113 Uiso 1 1 calc R . . 
C37 C -0.1519(4) 0.3829(3) 0.4385(3) 0.1051(11) Uani 1 1 d . B . 
H371 H -0.0601 0.3778 0.4561 0.126 Uiso 1 1 calc R . . 
C38 C -0.2190(5) 0.3025(3) 0.4490(3) 0.1090(12) Uani 1 1 d . . . 
H381 H -0.1887 0.2316 0.4811 0.131 Uiso 1 1 calc R B . 
C39 C -0.3389(5) 0.3417(3) 0.4048(3) 0.1141(13) Uani 1 1 d D B . 
H391 H -0.4165 0.3056 0.4090 0.137 Uiso 1 1 calc R A 1 
C40A C -0.3237(7) 0.4452(3) 0.3526(4) 0.1140(18) Uiso 0.50 1 d PD B 1 
H40A H -0.3671 0.4888 0.2955 0.137 Uiso 0.50 1 calc PR B 1 
C40B C -0.3611(4) 0.4429(4) 0.3973(6) 0.1140(18) Uiso 0.50 1 d PD B 2 
H40B H -0.4484 0.4835 0.3921 0.137 Uiso 0.50 1 calc PR B 2 

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 
O1 0.0910(13) 0.0684(11) 0.0757(12) -0.0323(9) 0.0128(10) -0.0264(10) 
N1 0.1023(19) 0.0850(18) 0.0825(17) -0.0176(14) 0.0057(14) -0.0310(15) 
N2 0.0702(12) 0.0602(12) 0.0593(12) -0.0281(9) -0.0009(10) -0.0062(10) 
N3 0.0668(12) 0.0557(11) 0.0597(12) -0.0253(9) -0.0032(10) -0.0047(9) 
N4 0.0863(16) 0.0719(15) 0.0731(14) -0.0265(11) -0.0026(12) -0.0198(13) 
C1 0.0709(16) 0.0788(18) 0.0595(15) -0.0193(13) -0.0037(12) -0.0119(14) 
C2 0.0626(14) 0.0645(14) 0.0498(13) -0.0183(11) -0.0079(10) -0.0061(11) 
C3 0.0679(15) 0.0837(18) 0.0587(14) -0.0325(13) 0.0073(12) -0.0133(13) 
C4 0.0744(16) 0.0753(16) 0.0681(16) -0.0418(13) 0.0035(12) -0.0069(13) 
C5 0.0611(13) 0.0562(13) 0.0513(12) -0.0213(10) -0.0076(10) -0.0041(10) 
C6 0.0676(14) 0.0570(14) 0.0559(13) -0.0240(11) 0.0034(11) -0.0022(11) 
C7 0.0753(16) 0.0562(14) 0.0645(15) -0.0247(11) 0.0011(12) -0.0050(12) 
C8 0.0601(13) 0.0504(13) 0.0578(13) -0.0222(10) -0.0071(10) -0.0026(10) 
C9 0.0722(16) 0.0642(15) 0.0666(15) -0.0338(12) 0.0080(12) -0.0097(12) 
C10 0.0816(17) 0.0633(15) 0.0769(17) -0.0401(13) 0.0039(13) -0.0119(13) 
C11 0.0645(14) 0.0579(14) 0.0623(14) -0.0248(11) -0.0042(11) -0.0086(11) 
C12 0.0741(16) 0.0688(16) 0.0638(15) -0.0304(12) 0.0055(12) -0.0118(13) 
C13 0.0759(16) 0.0607(14) 0.0646(15) -0.0328(12) 0.0015(12) -0.0077(12) 
C14 0.0819(18) 0.0770(18) 0.0666(16) -0.0286(13) -0.0005(13) -0.0179(14) 
C15 0.0836(18) 0.0770(18) 0.0725(17) -0.0336(14) -0.0028(14) -0.0188(14) 
C16 0.146(3) 0.0727(19) 0.081(2) -0.0317(16) 0.0144(19) -0.0280(19) 
C17 0.097(3) 0.157(4) 0.084(2) -0.018(2) -0.0230(19) -0.032(3) 
C18 0.177(4) 0.138(4) 0.072(2) -0.022(2) -0.007(2) -0.104(4) 
C19 0.177(4) 0.088(2) 0.079(2) -0.0378(18) 0.008(3) -0.043(3) 
C20 0.111(2) 0.076(2) 0.091(2) -0.0342(16) 0.0039(18) -0.0166(19) 
O2 0.0966(14) 0.0680(11) 0.0762(12) -0.0287(9) 0.0051(10) -0.0262(10) 
N5 0.109(2) 0.0850(19) 0.111(2) -0.0232(16) 0.0176(17) -0.0293(17) 
N6 0.0729(13) 0.0592(12) 0.0569(12) -0.0283(9) -0.0039(10) -0.0032(10) 
N7 0.0653(12) 0.0583(12) 0.0600(12) -0.0275(9) -0.0056(9) -0.0031(9) 
N8 0.0919(17) 0.0705(15) 0.0969(18) -0.0210(13) -0.0154(14) -0.0241(13) 
C21 0.0791(18) 0.0717(18) 0.0785(18) -0.0210(15) 0.0056(15) -0.0092(15) 
C22 0.0656(15) 0.0591(14) 0.0660(15) -0.0220(12) -0.0009(12) -0.0011(12) 
C23 0.0720(16) 0.0724(16) 0.0686(16) -0.0333(13) -0.0004(12) -0.0156(13) 
C24 0.0702(15) 0.0733(16) 0.0567(14) -0.0316(12) 0.0005(11) -0.0097(13) 
C25 0.0620(13) 0.0518(13) 0.0562(13) -0.0223(10) -0.0056(10) 0.0014(10) 
C26 0.107(2) 0.0754(17) 0.0583(15) -0.0343(13) 0.0003(14) -0.0156(16) 
C27 0.105(2) 0.0780(18) 0.0561(15) -0.0252(13) 0.0104(14) -0.0156(16) 
C28 0.0568(13) 0.0516(13) 0.0614(14) -0.0255(11) -0.0096(10) 0.0009(10) 
C29 0.0736(15) 0.0663(15) 0.0597(14) -0.0342(12) -0.0040(11) -0.0093(12) 
C30 0.0751(16) 0.0625(15) 0.0574(14) -0.0263(12) -0.0025(12) -0.0054(12) 
C31 0.0644(14) 0.0509(13) 0.0695(16) -0.0247(11) -0.0046(11) -0.0033(11) 
C32 0.0758(16) 0.0627(15) 0.0670(16) -0.0331(12) -0.0102(12) -0.0064(12) 
C33 0.0676(14) 0.0591(14) 0.0576(13) -0.0284(11) -0.0060(11) -0.0005(11) 
C34 0.0830(18) 0.0623(15) 0.0755(17) -0.0252(13) 0.0015(14) -0.0125(13) 
C35 0.0871(19) 0.0730(18) 0.083(2) -0.0210(15) -0.0064(15) -0.0196(15) 
C36 0.111(2) 0.0707(19) 0.099(2) -0.0335(17) 0.0106(18) -0.0245(17) 
C37 0.114(3) 0.070(2) 0.124(3) -0.0312(19) -0.009(2) -0.0084(19) 
C38 0.168(4) 0.077(2) 0.086(2) -0.0385(18) 0.016(2) -0.030(2) 
C39 0.117(3) 0.095(3) 0.135(3) -0.037(2) -0.009(3) -0.050(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 
O1 C11 1.362(3) . ? 
O1 C14 1.425(3) . ? 
N1 C1 1.138(3) . ? 
N2 N3 1.256(3) . ? 
N2 C5 1.421(3) . ? 
N3 C8 1.416(3) . ? 
N4 C17 1.335(4) . ? 
N4 C20 1.352(4) . ? 
N4 C16 1.439(3) . ? 
C1 C2 1.436(4) . ? 
C2 C3 1.378(3) . ? 
C2 C7 1.403(3) . ? 
C3 C4 1.366(3) . ? 
C3 H31 0.9300 . ? 
C4 C5 1.391(3) . ? 
C4 H41 0.9300 . ? 
C5 C6 1.399(3) . ? 
C6 C7 1.368(3) . ? 
C6 H61 0.9300 . ? 
C7 H71 0.9300 . ? 
C8 C13 1.380(3) . ? 
C8 C9 1.393(3) . ? 
C9 C10 1.357(3) . ? 
C9 H91 0.9300 . ? 
C10 C11 1.396(3) . ? 
C10 H101 0.9300 . ? 
C11 C12 1.379(3) . ? 
C12 C13 1.375(3) . ? 
C12 H121 0.9300 . ? 
C13 H131 0.9300 . ? 
C14 C15 1.520(4) . ? 
C14 H141 0.9700 . ? 
C14 H142 0.9700 . ? 
C15 C16 1.475(4) . ? 
C15 H151 0.9700 . ? 
C15 H152 0.9700 . ? 
C16 H161 0.9700 . ? 
C16 H162 0.9700 . ? 
C17 C18 1.368(6) . ? 
C17 H171 0.9300 . ? 
C18 C19 1.318(6) . ? 
C18 H181 0.9300 . ? 
C19 C20 1.299(4) . ? 
C19 H191 0.9300 . ? 
C20 H201 0.9300 . ? 
O2 C31 1.357(3) . ? 
O2 C34 1.419(3) . ? 
N5 C21 1.138(3) . ? 
N6 N7 1.250(3) . ? 
N6 C25 1.422(3) . ? 
N7 C28 1.412(3) . ? 
N8 C37 1.345(4) . ? 
N8 C40B 1.350(2) . ? 
N8 C40A 1.355(2) . ? 
N8 C36 1.446(3) . ? 
C21 C22 1.430(4) . ? 
C22 C27 1.383(4) . ? 
C22 C23 1.393(3) . ? 
C23 C24 1.363(3) . ? 
C23 H231 0.9300 . ? 
C24 C25 1.390(3) . ? 
C24 H241 0.9300 . ? 
C25 C26 1.384(3) . ? 
C26 C27 1.371(4) . ? 
C26 H261 0.9300 . ? 
C27 H271 0.9300 . ? 
C28 C29 1.377(3) . ? 
C28 C33 1.393(3) . ? 
C29 C30 1.376(3) . ? 
C29 H291 0.9300 . ? 
C30 C31 1.385(4) . ? 
C30 H301 0.9300 . ? 
C31 C32 1.391(3) . ? 
C32 C33 1.362(3) . ? 
C32 H321 0.9300 . ? 
C33 H331 0.9300 . ? 
C34 C35 1.517(4) . ? 
C34 H341 0.9700 . ? 
C34 H342 0.9700 . ? 
C35 C36 1.489(4) . ? 
C35 H351 0.9700 . ? 
C35 H352 0.9700 . ? 
C36 H361 0.9700 . ? 
C36 H362 0.9700 . ? 
C37 C38 1.310(4) . ? 
C37 H371 0.9300 . ? 
C38 C39 1.332(5) . ? 
C38 H381 0.9300 . ? 
C39 C40A 1.351(2) . ? 
C39 C40B 1.355(2) . ? 
C39 H391 0.9300 . ? 
C40A H40A 0.9300 . ? 
C40B H40B 0.9300 . ? 

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 
C11 O1 C14 118.57(19) . . ? 
N3 N2 C5 113.46(19) . . ? 
N2 N3 C8 114.1(2) . . ? 
C17 N4 C20 106.6(3) . . ? 
C17 N4 C16 129.0(3) . . ? 
C20 N4 C16 124.5(3) . . ? 
N1 C1 C2 179.6(3) . . ? 
C3 C2 C7 120.0(2) . . ? 
C3 C2 C1 120.2(2) . . ? 
C7 C2 C1 119.8(2) . . ? 
C4 C3 C2 120.2(2) . . ? 
C4 C3 H31 119.9 . . ? 
C2 C3 H31 119.9 . . ? 
C3 C4 C5 120.8(2) . . ? 
C3 C4 H41 119.6 . . ? 
C5 C4 H41 119.6 . . ? 
C4 C5 C6 119.0(2) . . ? 
C4 C5 N2 115.8(2) . . ? 
C6 C5 N2 125.2(2) . . ? 
C7 C6 C5 120.4(2) . . ? 
C7 C6 H61 119.8 . . ? 
C5 C6 H61 119.8 . . ? 
C6 C7 C2 119.6(2) . . ? 
C6 C7 H71 120.2 . . ? 
C2 C7 H71 120.2 . . ? 
C13 C8 C9 119.2(2) . . ? 
C13 C8 N3 116.2(2) . . ? 
C9 C8 N3 124.6(2) . . ? 
C10 C9 C8 120.6(2) . . ? 
C10 C9 H91 119.7 . . ? 
C8 C9 H91 119.7 . . ? 
C9 C10 C11 119.8(2) . . ? 
C9 C10 H101 120.1 . . ? 
C11 C10 H101 120.1 . . ? 
O1 C11 C12 125.8(2) . . ? 
O1 C11 C10 114.1(2) . . ? 
C12 C11 C10 120.0(2) . . ? 
C13 C12 C11 119.6(2) . . ? 
C13 C12 H121 120.2 . . ? 
C11 C12 H121 120.2 . . ? 
C12 C13 C8 120.7(2) . . ? 
C12 C13 H131 119.7 . . ? 
C8 C13 H131 119.7 . . ? 
O1 C14 C15 105.8(2) . . ? 
O1 C14 H141 110.6 . . ? 
C15 C14 H141 110.6 . . ? 
O1 C14 H142 110.6 . . ? 
C15 C14 H142 110.6 . . ? 
H141 C14 H142 108.7 . . ? 
C16 C15 C14 112.3(2) . . ? 
C16 C15 H151 109.2 . . ? 
C14 C15 H151 109.2 . . ? 
C16 C15 H152 109.2 . . ? 
C14 C15 H152 109.2 . . ? 
H151 C15 H152 107.9 . . ? 
N4 C16 C15 113.1(2) . . ? 
N4 C16 H161 109.0 . . ? 
C15 C16 H161 109.0 . . ? 
N4 C16 H162 109.0 . . ? 
C15 C16 H162 109.0 . . ? 
H161 C16 H162 107.8 . . ? 
N4 C17 C18 106.7(4) . . ? 
N4 C17 H171 126.6 . . ? 
C18 C17 H171 126.6 . . ? 
C19 C18 C17 108.6(3) . . ? 
C19 C18 H181 125.7 . . ? 
C17 C18 H181 125.7 . . ? 
C20 C19 C18 107.7(4) . . ? 
C20 C19 H191 126.1 . . ? 
C18 C19 H191 126.1 . . ? 
C19 C20 N4 110.2(4) . . ? 
C19 C20 H201 124.9 . . ? 
N4 C20 H201 124.9 . . ? 
C31 O2 C34 119.3(2) . . ? 
N7 N6 C25 113.6(2) . . ? 
N6 N7 C28 114.6(2) . . ? 
C37 N8 C40B 103.8(3) . . ? 
C37 N8 C40A 100.9(3) . . ? 
C40B N8 C40A 29.5(4) . . ? 
C37 N8 C36 124.4(3) . . ? 
C40B N8 C36 131.6(3) . . ? 
C40A N8 C36 128.8(3) . . ? 
N5 C21 C22 179.2(3) . . ? 
C27 C22 C23 119.4(2) . . ? 
C27 C22 C21 120.4(2) . . ? 
C23 C22 C21 120.2(2) . . ? 
C24 C23 C22 120.1(2) . . ? 
C24 C23 H231 120.0 . . ? 
C22 C23 H231 120.0 . . ? 
C23 C24 C25 120.6(2) . . ? 
C23 C24 H241 119.7 . . ? 
C25 C24 H241 119.7 . . ? 
C26 C25 C24 119.1(2) . . ? 
C26 C25 N6 115.8(2) . . ? 
C24 C25 N6 125.1(2) . . ? 
C27 C26 C25 120.4(2) . . ? 
C27 C26 H261 119.8 . . ? 
C25 C26 H261 119.8 . . ? 
C26 C27 C22 120.3(2) . . ? 
C26 C27 H271 119.9 . . ? 
C22 C27 H271 119.9 . . ? 
C29 C28 C33 119.2(2) . . ? 
C29 C28 N7 116.4(2) . . ? 
C33 C28 N7 124.5(2) . . ? 
C30 C29 C28 121.2(2) . . ? 
C30 C29 H291 119.4 . . ? 
C28 C29 H291 119.4 . . ? 
C29 C30 C31 119.1(2) . . ? 
C29 C30 H301 120.4 . . ? 
C31 C30 H301 120.4 . . ? 
O2 C31 C30 125.8(2) . . ? 
O2 C31 C32 114.2(2) . . ? 
C30 C31 C32 120.1(2) . . ? 
C33 C32 C31 120.2(2) . . ? 
C33 C32 H321 119.9 . . ? 
C31 C32 H321 119.9 . . ? 
C32 C33 C28 120.3(2) . . ? 
C32 C33 H331 119.9 . . ? 
C28 C33 H331 119.9 . . ? 
O2 C34 C35 105.7(2) . . ? 
O2 C34 H341 110.6 . . ? 
C35 C34 H341 110.6 . . ? 
O2 C34 H342 110.6 . . ? 
C35 C34 H342 110.6 . . ? 
H341 C34 H342 108.7 . . ? 
C36 C35 C34 112.1(3) . . ? 
C36 C35 H351 109.2 . . ? 
C34 C35 H351 109.2 . . ? 
C36 C35 H352 109.2 . . ? 
C34 C35 H352 109.2 . . ? 
H351 C35 H352 107.9 . . ? 
N8 C36 C35 111.9(3) . . ? 
N8 C36 H361 109.2 . . ? 
C35 C36 H361 109.2 . . ? 
N8 C36 H362 109.2 . . ? 
C35 C36 H362 109.2 . . ? 
H361 C36 H362 107.9 . . ? 
C38 C37 N8 110.9(4) . . ? 
C38 C37 H371 124.6 . . ? 
N8 C37 H371 124.6 . . ? 
C37 C38 C39 106.9(4) . . ? 
C37 C38 H381 126.6 . . ? 
C39 C38 H381 126.6 . . ? 
C38 C39 C40A 105.1(4) . . ? 
C38 C39 C40B 105.6(4) . . ? 
C40A C39 C40B 29.5(4) . . ? 
C38 C39 H391 127.4 . . ? 
C40A C39 H391 127.4 . . ? 
C40B C39 H391 119.6 . . ? 
C39 C40A N8 107.4(3) . . ? 
C39 C40A H40A 126.3 . . ? 
N8 C40A H40A 126.3 . . ? 
N8 C40B C39 107.5(3) . . ? 
N8 C40B H40B 126.2 . . ? 
C39 C40B H40B 126.2 . . ? 

_diffrn_measured_fraction_theta_max    0.992 
_diffrn_reflns_theta_full              24.00 
_diffrn_measured_fraction_theta_full   0.992 
_refine_diff_density_max    0.642 
_refine_diff_density_min   -0.266 
_refine_diff_density_rms    0.042 

# end of file

data_y639-3NO2 
_database_code_CSD                  169301

#
# CIF file for compound "3-NO2" (C19H18N4O3)
# To accompany revised
# submission b105976a to J. Mater. Chem.
#


_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
'C19 H18 N4 O3' 
_chemical_formula_weight          350.37 

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' 
'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' 
'H'  'H'   0.0000   0.0000 
'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                    11.8709(18) 
_cell_length_b                    7.6449(12) 
_cell_length_c                    20.891(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  111.696(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1761.6(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 

_cell_measurement_reflns_used     5770 
_cell_measurement_theta_min       3.10 
_cell_measurement_theta_max       27.80 

_exptl_crystal_description        blade 
_exptl_crystal_colour             orange 
_exptl_crystal_size_max           0.90 
_exptl_crystal_size_mid           0.12 
_exptl_crystal_size_min           0.02 

_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.321 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              736 
_exptl_absorpt_coefficient_mu     0.092 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.922 
_exptl_absorpt_correction_T_max   0.998 
_exptl_absorpt_process_details    'SADABS (Bruker, 1999)' 

_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.69230 
_diffrn_radiation_type            synchrotron 
_diffrn_radiation_source          'Daresbury SRS station 9.8' 
_diffrn_radiation_monochromator   'silicon 111' 
_diffrn_measurement_device_type   'Bruker SMART CCD' 
_diffrn_measurement_method        \w 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         0 

_diffrn_reflns_number             16650 
_diffrn_reflns_av_R_equivalents   0.0538 
_diffrn_reflns_av_sigmaI/netI     0.0568 
_diffrn_reflns_limit_h_min        -16 
_diffrn_reflns_limit_h_max        16 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -29 
_diffrn_reflns_limit_l_max        28 
_diffrn_reflns_theta_min          1.80 
_diffrn_reflns_theta_max          29.21 
_reflns_number_total              4764 
_reflns_number_gt                 2416 
_reflns_threshold_expression      'I>2\s(I)' 

_computing_data_collection        'SMART (Bruker, 1999)'  
_computing_cell_refinement        'SMART (Bruker, 1999)'   
_computing_data_reduction         'SMART (Bruker, 1999)'  
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)' 
_computing_publication_material   'SHELXL-97 (Sheldrick, 1997)' 


_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^)+(0.1296P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          4764 
_refine_ls_number_parameters      356 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.117 
_refine_ls_R_factor_gt            0.068 
_refine_ls_wR_factor_ref          0.198 
_refine_ls_wR_factor_gt           0.180 
_refine_ls_goodness_of_fit_ref    0.88 
_refine_ls_restrained_S_all       0.88 
_refine_ls_shift/su_max           0.045 
_refine_ls_shift/su_mean          0.004 

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 
O1 O -0.54147(15) 0.3878(4) -0.16064(10) 0.1326(9) Uani 1 1 d . A . 
O2 O -0.51401(17) 0.5461(4) -0.23739(10) 0.1292(8) Uani 1 1 d . A . 
N1 N -0.47650(15) 0.4559(3) -0.18653(10) 0.0849(6) Uani 1 1 d . . . 
C1A C -0.3499(6) 0.4413(10) -0.1583(4) 0.0492(14) Uani 0.677(11) 1 d P A 1 
C2A C -0.3074(6) 0.3316(11) -0.0991(4) 0.0658(19) Uani 0.677(11) 1 d P A 1 
H2A H -0.3588 0.2795 -0.0802 0.079 Uiso 0.677(11) 1 calc PR A 1 
C3A C -0.1722(7) 0.3071(12) -0.0698(4) 0.0632(16) Uani 0.677(11) 1 d P A 1 
H3A H -0.1363 0.2337 -0.0323 0.076 Uiso 0.677(11) 1 calc PR A 1 
C4A C -0.1022(4) 0.3946(7) -0.0992(3) 0.0471(11) Uani 0.677(11) 1 d P A 1 
C5A C -0.1531(5) 0.5008(8) -0.1557(3) 0.0569(12) Uani 0.677(11) 1 d P A 1 
H5A H -0.1034 0.5582 -0.1745 0.068 Uiso 0.677(11) 1 calc PR A 1 
C6A C -0.2732(7) 0.5226(10) -0.1840(4) 0.0562(13) Uani 0.677(11) 1 d P A 1 
H6A H -0.3054 0.5949 -0.2223 0.067 Uiso 0.677(11) 1 calc PR A 1 
N2A N 0.0297(6) 0.3867(4) -0.07669(19) 0.0610(11) Uani 0.677(11) 1 d P A 1 
N3A N 0.0711(6) 0.2909(4) -0.02753(18) 0.0567(10) Uani 0.677(11) 1 d P A 1 
C7A C 0.2008(6) 0.2719(9) -0.0045(4) 0.0503(13) Uani 0.677(11) 1 d P A 1 
C8A C 0.2531(13) 0.179(3) 0.0502(9) 0.075(4) Uani 0.677(11) 1 d P A 1 
H8A H 0.2054 0.1296 0.0720 0.090 Uiso 0.677(11) 1 calc PR A 1 
C9A C 0.3684(17) 0.153(3) 0.0759(12) 0.071(4) Uani 0.677(11) 1 d P A 1 
H9A H 0.3999 0.0862 0.1159 0.085 Uiso 0.677(11) 1 calc PR A 1 
C10A C 0.4461(12) 0.2153(19) 0.0480(7) 0.071(3) Uani 0.677(11) 1 d P A 1 
C11A C 0.3961(8) 0.3038(14) -0.0098(5) 0.0662(18) Uani 0.677(11) 1 d P A 1 
H11A H 0.4450 0.3428 -0.0329 0.079 Uiso 0.677(11) 1 calc PR A 1 
C12A C 0.2771(10) 0.3398(15) -0.0365(5) 0.063(2) Uani 0.677(11) 1 d P A 1 
H12A H 0.2452 0.4089 -0.0757 0.076 Uiso 0.677(11) 1 calc PR A 1 
C1B C -0.3404(10) 0.4041(15) -0.1446(5) 0.039(3) Uani 0.323(11) 1 d PR A 2 
C2B C -0.2957(10) 0.2991(15) -0.0948(5) 0.065(5) Uani 0.323(11) 1 d PR A 2 
H2B H -0.3529 0.2298 -0.0861 0.078 Uiso 0.323(11) 1 calc PR A 2 
C3B C -0.1976(17) 0.274(3) -0.0583(11) 0.065(3) Uani 0.323(11) 1 d P A 2 
H3B H -0.1806 0.2072 -0.0186 0.078 Uiso 0.323(11) 1 calc PR A 2 
C4B C -0.1044(9) 0.3461(13) -0.0758(5) 0.0379(18) Uani 0.323(11) 1 d P A 2 
C5B C -0.1347(8) 0.4575(14) -0.1297(6) 0.049(2) Uani 0.323(11) 1 d P A 2 
H5B H -0.0760 0.5130 -0.1420 0.058 Uiso 0.323(11) 1 calc PR A 2 
C6B C -0.264(2) 0.487(3) -0.1677(9) 0.079(4) Uani 0.323(11) 1 d P A 2 
H6B H -0.2914 0.5594 -0.2061 0.095 Uiso 0.323(11) 1 calc PR A 2 
N2B N 0.0101(8) 0.2973(8) -0.0385(3) 0.0473(17) Uani 0.323(11) 1 d P A 2 
N3B N 0.0951(8) 0.3611(8) -0.0583(4) 0.0420(18) Uani 0.323(11) 1 d P A 2 
C7B C 0.2171(11) 0.3106(14) -0.0192(7) 0.0353(19) Uani 0.323(11) 1 d P A 2 
C8B C 0.2529(18) 0.211(5) 0.0483(16) 0.061(6) Uani 0.323(11) 1 d P A 2 
H8B H 0.1958 0.1812 0.0672 0.073 Uiso 0.323(11) 1 calc PR A 2 
C9B C 0.386(3) 0.160(6) 0.084(3) 0.056(4) Uani 0.323(11) 1 d P A 2 
H9B H 0.4165 0.1027 0.1262 0.067 Uiso 0.323(11) 1 calc PR A 2 
C10B C 0.459(2) 0.209(3) 0.0465(9) 0.035(3) Uani 0.323(11) 1 d P A 2 
C11B C 0.4186(12) 0.321(2) -0.0175(7) 0.039(2) Uani 0.323(11) 1 d P A 2 
H11B H 0.4742 0.3623 -0.0357 0.047 Uiso 0.323(11) 1 calc PR A 2 
C12B C 0.295(2) 0.363(3) -0.0484(12) 0.056(3) Uani 0.323(11) 1 d P A 2 
H12B H 0.2663 0.4259 -0.0893 0.067 Uiso 0.323(11) 1 calc PR A 2 
O3 O 0.57347(12) 0.1826(2) 0.06932(8) 0.0775(4) Uani 1 1 d . . . 
N4 N 0.96497(13) 0.1576(2) 0.17885(8) 0.0609(4) Uani 1 1 d . . . 
C13 C 0.62614(19) 0.0864(3) 0.13067(13) 0.0854(7) Uani 1 1 d . A . 
H131 H 0.5828 -0.0229 0.1274 0.102 Uiso 1 1 calc R . . 
H132 H 0.6214 0.1525 0.1692 0.102 Uiso 1 1 calc R . . 
C14 C 0.75654(18) 0.0501(3) 0.14179(14) 0.0856(7) Uani 1 1 d . . . 
H141 H 0.7906 -0.0229 0.1824 0.103 Uiso 1 1 calc R A . 
H142 H 0.7588 -0.0167 0.1028 0.103 Uiso 1 1 calc R . . 
C15 C 0.83482(19) 0.2049(3) 0.15046(13) 0.0792(6) Uani 1 1 d . A . 
H151 H 0.8183 0.2873 0.1812 0.095 Uiso 1 1 calc R . . 
H152 H 0.8160 0.2617 0.1062 0.095 Uiso 1 1 calc R . . 
C16 C 1.04110(17) 0.1892(3) 0.24475(10) 0.0637(5) Uani 1 1 d . . . 
H161 H 1.0210 0.2476 0.2781 0.076 Uiso 1 1 calc R . . 
C17 C 1.15054(16) 0.1215(3) 0.25353(10) 0.0652(5) Uani 1 1 d . . . 
H171 H 1.2197 0.1270 0.2935 0.078 Uiso 1 1 calc R . . 
C18 C 1.14116(18) 0.0416(3) 0.19179(11) 0.0673(5) Uani 1 1 d . . . 
H181 H 1.2024 -0.0176 0.1831 0.081 Uiso 1 1 calc R . . 
C19 C 1.02635(19) 0.0665(3) 0.14700(10) 0.0689(5) Uani 1 1 d . . . 
H191 H 0.9949 0.0272 0.1017 0.083 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 
O1 0.0491(9) 0.229(3) 0.1205(14) 0.0168(15) 0.0326(9) -0.0178(12) 
O2 0.0731(12) 0.186(2) 0.1060(14) 0.0390(15) 0.0069(10) 0.0229(12) 
N1 0.0443(9) 0.1256(17) 0.0773(11) -0.0042(11) 0.0138(8) -0.0040(10) 
C1A 0.043(2) 0.053(3) 0.045(3) 0.007(2) 0.0085(19) 0.0003(18) 
C2A 0.052(3) 0.064(3) 0.083(5) -0.002(3) 0.027(3) -0.002(2) 
C3A 0.056(4) 0.071(4) 0.059(3) 0.004(2) 0.016(3) 0.003(3) 
C4A 0.0445(18) 0.047(3) 0.046(3) -0.001(2) 0.012(2) -0.0017(18) 
C5A 0.049(2) 0.058(3) 0.066(3) 0.006(2) 0.025(2) -0.0069(17) 
C6A 0.050(2) 0.060(3) 0.061(3) 0.011(2) 0.023(2) -0.007(2) 
N2A 0.056(3) 0.0630(16) 0.0639(17) -0.0049(13) 0.0216(18) -0.0060(15) 
N3A 0.056(3) 0.0599(16) 0.0540(16) -0.0065(12) 0.0200(18) -0.0065(16) 
C7A 0.039(2) 0.055(3) 0.060(4) -0.007(2) 0.023(2) -0.0105(19) 
C8A 0.069(6) 0.080(7) 0.082(6) -0.002(4) 0.037(5) -0.007(3) 
C9A 0.061(9) 0.082(4) 0.065(5) 0.005(3) 0.016(6) -0.005(6) 
C10A 0.044(4) 0.072(5) 0.087(5) -0.010(4) 0.013(3) 0.011(3) 
C11A 0.062(4) 0.077(3) 0.077(3) 0.003(2) 0.045(3) -0.014(3) 
C12A 0.067(4) 0.068(4) 0.051(4) 0.006(3) 0.017(3) 0.003(3) 
C1B 0.025(3) 0.050(6) 0.036(5) 0.021(3) 0.004(3) 0.008(3) 
C2B 0.055(7) 0.076(8) 0.054(7) 0.008(5) 0.008(5) 0.009(5) 
C3B 0.058(6) 0.073(8) 0.072(8) -0.008(5) 0.035(5) -0.013(5) 
C4B 0.050(4) 0.034(4) 0.031(4) 0.004(3) 0.016(3) -0.004(3) 
C5B 0.042(5) 0.059(6) 0.047(6) 0.021(4) 0.018(5) -0.005(4) 
C6B 0.096(9) 0.081(9) 0.065(7) 0.036(5) 0.037(6) 0.011(6) 
N2B 0.026(3) 0.061(3) 0.053(3) -0.004(2) 0.012(3) -0.003(3) 
N3B 0.028(4) 0.049(3) 0.046(3) -0.004(2) 0.010(3) 0.000(2) 
C7B 0.030(4) 0.035(4) 0.043(5) 0.002(3) 0.016(3) -0.005(3) 
C8B 0.027(6) 0.071(10) 0.082(13) -0.029(8) 0.017(7) 0.001(5) 
C9B 0.024(4) 0.075(10) 0.063(9) 0.003(7) 0.009(5) 0.004(5) 
C10B 0.025(4) 0.043(6) 0.041(5) -0.004(4) 0.015(4) -0.006(4) 
C11B 0.029(4) 0.051(4) 0.040(4) 0.003(3) 0.018(3) -0.012(3) 
C12B 0.061(7) 0.056(6) 0.047(6) 0.006(4) 0.017(5) 0.009(5) 
O3 0.0494(8) 0.0915(11) 0.0881(10) 0.0062(8) 0.0212(7) 0.0052(7) 
N4 0.0468(8) 0.0580(9) 0.0714(9) -0.0094(7) 0.0142(7) -0.0034(6) 
C13 0.0592(12) 0.0836(15) 0.1063(17) 0.0224(13) 0.0224(11) 0.0089(11) 
C14 0.0490(11) 0.0766(14) 0.1182(18) -0.0005(13) 0.0155(11) 0.0072(10) 
C15 0.0594(12) 0.0622(12) 0.1020(16) -0.0034(11) 0.0136(11) 0.0086(10) 
C16 0.0583(11) 0.0688(12) 0.0647(11) -0.0136(9) 0.0234(9) -0.0107(9) 
C17 0.0512(10) 0.0712(12) 0.0657(11) 0.0035(9) 0.0126(8) -0.0077(9) 
C18 0.0603(11) 0.0638(12) 0.0864(13) 0.0034(10) 0.0372(10) 0.0021(9) 
C19 0.0708(13) 0.0726(13) 0.0614(10) -0.0112(9) 0.0222(10) -0.0056(10) 

_geom_special_details 
; 
All esds (except the esd in the dihedral angle between two l.s. planes) 
are estimated using the full covariance matrix.  The cell esds are taken 
into account individually in the estimation of esds in distances, angles 
and torsion angles; correlations between esds in cell parameters are only 
used when they are defined by crystal symmetry.  An approximate (isotropic) 
treatment of cell esds is used for estimating esds involving l.s. planes. 
; 

loop_ 
_geom_bond_atom_site_label_1 
_geom_bond_atom_site_label_2 
_geom_bond_distance 
_geom_bond_site_symmetry_2 
_geom_bond_publ_flag 
O1 N1 1.212(3) . ? 
O2 N1 1.205(3) . ? 
N1 C1A 1.401(7) . ? 
N1 C1B 1.578(11) . ? 
C1A C6A 1.366(11) . ? 
C1A C2A 1.424(7) . ? 
C2A C3A 1.503(11) . ? 
C2A H2A 0.9300 . ? 
C3A C4A 1.376(6) . ? 
C3A H3A 0.9300 . ? 
C4A C5A 1.375(5) . ? 
C4A N2A 1.460(8) . ? 
C5A C6A 1.337(11) . ? 
C5A H5A 0.9300 . ? 
C6A H6A 0.9300 . ? 
N2A N3A 1.208(7) . ? 
N3A C7A 1.441(9) . ? 
C7A C8A 1.29(2) . ? 
C7A C12A 1.408(9) . ? 
C8A C9A 1.29(2) . ? 
C8A H8A 0.9300 . ? 
C9A C10A 1.35(3) . ? 
C9A H9A 0.9300 . ? 
C10A C11A 1.318(15) . ? 
C10A O3 1.431(14) . ? 
C11A C12A 1.341(14) . ? 
C11A H11A 0.9300 . ? 
C12A H12A 0.9300 . ? 
C1B C2B 1.2641 . ? 
C1B C6B 1.34(3) . ? 
C2B C3B 1.15(2) . ? 
C2B H2B 0.9300 . ? 
C3B C4B 1.401(10) . ? 
C3B H3B 0.9300 . ? 
C4B N2B 1.346(15) . ? 
C4B C5B 1.350(8) . ? 
C5B C6B 1.46(3) . ? 
C5B H5B 0.9300 . ? 
C6B H6B 0.9300 . ? 
N2B N3B 1.317(12) . ? 
N3B C7B 1.428(14) . ? 
C7B C12B 1.339(18) . ? 
C7B C8B 1.52(4) . ? 
C8B C9B 1.53(4) . ? 
C8B H8B 0.9300 . ? 
C9B C10B 1.41(5) . ? 
C9B H9B 0.9300 . ? 
C10B O3 1.28(2) . ? 
C10B C11B 1.51(2) . ? 
C11B C12B 1.41(3) . ? 
C11B H11B 0.9300 . ? 
C12B H12B 0.9300 . ? 
O3 C13 1.408(3) . ? 
N4 C19 1.348(2) . ? 
N4 C16 1.360(2) . ? 
N4 C15 1.480(2) . ? 
C13 C14 1.504(3) . ? 
C13 H131 0.9700 . ? 
C13 H132 0.9700 . ? 
C14 C15 1.474(3) . ? 
C14 H141 0.9700 . ? 
C14 H142 0.9700 . ? 
C15 H151 0.9700 . ? 
C15 H152 0.9700 . ? 
C16 C17 1.346(3) . ? 
C16 H161 0.9300 . ? 
C17 C18 1.394(3) . ? 
C17 H171 0.9300 . ? 
C18 C19 1.351(3) . ? 
C18 H181 0.9300 . ? 
C19 H191 0.9300 . ? 

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 
O2 N1 O1 123.4(2) . . ? 
O2 N1 C1A 113.9(4) . . ? 
O1 N1 C1A 122.6(4) . . ? 
O2 N1 C1B 127.0(3) . . ? 
O1 N1 C1B 109.5(3) . . ? 
C1A N1 C1B 13.4(6) . . ? 
C6A C1A N1 124.4(6) . . ? 
C6A C1A C2A 122.4(5) . . ? 
N1 C1A C2A 113.1(6) . . ? 
C1A C2A C3A 114.1(4) . . ? 
C1A C2A H2A 122.9 . . ? 
C3A C2A H2A 122.9 . . ? 
C4A C3A C2A 119.3(6) . . ? 
C4A C3A H3A 120.4 . . ? 
C2A C3A H3A 120.4 . . ? 
C5A C4A C3A 121.6(5) . . ? 
C5A C4A N2A 112.4(5) . . ? 
C3A C4A N2A 126.1(6) . . ? 
C6A C5A C4A 120.8(5) . . ? 
C6A C5A H5A 119.6 . . ? 
C4A C5A H5A 119.6 . . ? 
C5A C6A C1A 121.8(5) . . ? 
C5A C6A H6A 119.1 . . ? 
C1A C6A H6A 119.1 . . ? 
N3A N2A C4A 110.5(7) . . ? 
N2A N3A C7A 113.2(8) . . ? 
C8A C7A C12A 116.0(9) . . ? 
C8A C7A N3A 117.1(8) . . ? 
C12A C7A N3A 126.8(8) . . ? 
C9A C8A C7A 123.0(17) . . ? 
C9A C8A H8A 118.5 . . ? 
C7A C8A H8A 118.5 . . ? 
C8A C9A C10A 124(2) . . ? 
C8A C9A H9A 118.1 . . ? 
C10A C9A H9A 118.2 . . ? 
C11A C10A C9A 115.5(14) . . ? 
C11A C10A O3 116.2(9) . . ? 
C9A C10A O3 128.0(15) . . ? 
C10A C11A C12A 122.3(8) . . ? 
C10A C11A H11A 118.8 . . ? 
C12A C11A H11A 118.8 . . ? 
C11A C12A C7A 119.4(8) . . ? 
C11A C12A H12A 120.3 . . ? 
C7A C12A H12A 120.3 . . ? 
C2B C1B C6B 117.6(9) . . ? 
C2B C1B N1 130.4(3) . . ? 
C6B C1B N1 112.0(10) . . ? 
C3B C2B C1B 131.8(9) . . ? 
C3B C2B H2B 114.1 . . ? 
C1B C2B H2B 114.1 . . ? 
C2B C3B C4B 117.7(16) . . ? 
C2B C3B H3B 121.1 . . ? 
C4B C3B H3B 121.1 . . ? 
N2B C4B C5B 123.9(9) . . ? 
N2B C4B C3B 117.7(13) . . ? 
C5B C4B C3B 118.3(12) . . ? 
C4B C5B C6B 116.9(10) . . ? 
C4B C5B H5B 121.5 . . ? 
C6B C5B H5B 121.5 . . ? 
C1B C6B C5B 116.6(10) . . ? 
C1B C6B H6B 121.7 . . ? 
C5B C6B H6B 121.7 . . ? 
N3B N2B C4B 116.3(10) . . ? 
N2B N3B C7B 117.0(10) . . ? 
C12B C7B N3B 112.4(12) . . ? 
C12B C7B C8B 124.7(15) . . ? 
N3B C7B C8B 122.9(10) . . ? 
C7B C8B C9B 118(3) . . ? 
C7B C8B H8B 121.2 . . ? 
C9B C8B H8B 121.2 . . ? 
C10B C9B C8B 113(4) . . ? 
C10B C9B H9B 123.3 . . ? 
C8B C9B H9B 123.3 . . ? 
O3 C10B C9B 122(2) . . ? 
O3 C10B C11B 111.1(12) . . ? 
C9B C10B C11B 126(2) . . ? 
C12B C11B C10B 117.8(13) . . ? 
C12B C11B H11B 121.1 . . ? 
C10B C11B H11B 121.1 . . ? 
C7B C12B C11B 120.1(16) . . ? 
C7B C12B H12B 119.9 . . ? 
C11B C12B H12B 119.9 . . ? 
C10B O3 C13 118.2(7) . . ? 
C10B O3 C10A 3.5(12) . . ? 
C13 O3 C10A 115.9(6) . . ? 
C19 N4 C16 108.24(16) . . ? 
C19 N4 C15 127.06(17) . . ? 
C16 N4 C15 124.53(17) . . ? 
O3 C13 C14 108.81(19) . . ? 
O3 C13 H131 109.9 . . ? 
C14 C13 H131 109.9 . . ? 
O3 C13 H132 109.9 . . ? 
C14 C13 H132 109.9 . . ? 
H131 C13 H132 108.3 . . ? 
C15 C14 C13 115.92(19) . . ? 
C15 C14 H141 108.3 . . ? 
C13 C14 H141 108.3 . . ? 
C15 C14 H142 108.3 . . ? 
C13 C14 H142 108.3 . . ? 
H141 C14 H142 107.4 . . ? 
C14 C15 N4 111.76(17) . . ? 
C14 C15 H151 109.3 . . ? 
N4 C15 H151 109.3 . . ? 
C14 C15 H152 109.3 . . ? 
N4 C15 H152 109.3 . . ? 
H151 C15 H152 107.9 . . ? 
C17 C16 N4 108.44(17) . . ? 
C17 C16 H161 125.8 . . ? 
N4 C16 H161 125.8 . . ? 
C16 C17 C18 107.42(16) . . ? 
C16 C17 H171 126.3 . . ? 
C18 C17 H171 126.3 . . ? 
C19 C18 C17 107.11(17) . . ? 
C19 C18 H181 126.4 . . ? 
C17 C18 H181 126.4 . . ? 
N4 C19 C18 108.77(17) . . ? 
N4 C19 H191 125.6 . . ? 
C18 C19 H191 125.6 . . ? 

_diffrn_measured_fraction_theta_max    0.922 
_diffrn_reflns_theta_full              29.21 
_diffrn_measured_fraction_theta_full   0.922 
_refine_diff_density_max    0.257 
_refine_diff_density_min   -0.267 
_refine_diff_density_rms    0.054 

# end of file