# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is (c) The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2008


data_global
_journal_name_full               'New J.Chem.'

_journal_coden_Cambridge         0440
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Dionisia Sanz'
_publ_contact_author_email       DSANZ@CCIA.UNED.ES

_publ_section_title              
;
A Theoretical and Experimental NMR Study of the
Tautomerism of two Phenylene-bis-C-Substituted Pyrazoles
;
loop_
_publ_author_name
'Dionisia Sanz del Castillo'
'Ibon Alkorta'
'Rosa Claramunt'
'J Elguero'
'Tobias Ruffer'
;
W.Thiel
;

# Attachment 'B803855D_2ndRev_compound_1.txt'

data_ii229a
_database_code_depnum_ccdc_archive 'CCDC 679321'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H40 N12 O'
_chemical_formula_weight         704.84

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)/n

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

_cell_length_a                   15.3449(19)
_cell_length_b                   9.6588(12)
_cell_length_c                   26.538(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.190(2)
_cell_angle_gamma                90.00
_cell_volume                     3777.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9317
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13355
_diffrn_reflns_av_R_equivalents  0.1093
_diffrn_reflns_av_sigmaI/netI    0.2019
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         26.02
_reflns_number_total             6804
_reflns_number_gt                2313
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SAINT
_computing_data_reduction        XPREP
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 218 restraints have been
used in order to refine the disordered diethyl ether molecule anisotropically
as well as reaching lower hirshfeld values of atoms possesing large Uij
values. Measurements were limited due to release of Et2O, destroying the
crystal quality. Therefore four different measurements have been combined.
Large crystals have been used for measurement, reducing exposure times.
Problems in reaching completeness and a good ratio between observed/unique
reflections are originated by the mentioned release of Et2O.

;

_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^)+(0.0526P)^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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         6804
_refine_ls_number_parameters     527
_refine_ls_number_restraints     218
_refine_ls_R_factor_all          0.2399
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.1440
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   0.801
_refine_ls_restrained_S_all      0.795
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4842(2) 0.9144(4) 0.23583(12) 0.0559(10) Uani 1 1 d U . .
N2 N 0.4055(2) 0.9477(4) 0.19943(13) 0.0582(10) Uani 1 1 d U . .
H2N H 0.3842 1.0326 0.1934 0.070 Uiso 1 1 calc R . .
N3 N 0.5881(2) 0.2644(4) 0.26803(13) 0.0551(10) Uani 1 1 d . . .
N4 N 0.6209(2) 0.1345(4) 0.26636(13) 0.0624(11) Uani 1 1 d . . .
H4N H 0.5865 0.0615 0.2554 0.075 Uiso 1 1 calc R . .
C1 C 0.3640(3) 0.8351(5) 0.17375(16) 0.0622(13) Uani 1 1 d U . .
H1 H 0.3085 0.8336 0.1466 0.075 Uiso 1 1 calc R . .
C2 C 0.4168(3) 0.7232(5) 0.19407(16) 0.0572(12) Uani 1 1 d . . .
H2 H 0.4052 0.6290 0.1843 0.069 Uiso 1 1 calc R . .
C3 C 0.4917(3) 0.7768(5) 0.23238(15) 0.0510(12) Uani 1 1 d U . .
C4 C 0.7117(3) 0.1301(6) 0.28332(18) 0.0794(16) Uani 1 1 d . . .
H4 H 0.7488 0.0506 0.2850 0.095 Uiso 1 1 calc R . .
C5 C 0.7408(3) 0.2618(6) 0.29786(17) 0.0745(15) Uani 1 1 d . . .
H5 H 0.8016 0.2923 0.3121 0.089 Uiso 1 1 calc R . .
C6 C 0.6621(3) 0.3417(5) 0.28723(15) 0.0534(12) Uani 1 1 d . . .
C7 C 0.5680(3) 0.7029(5) 0.26843(15) 0.0533(12) Uani 1 1 d . . .
C8 C 0.5794(3) 0.5629(5) 0.26271(15) 0.0511(12) Uani 1 1 d . . .
H8 H 0.5360 0.5146 0.2359 0.061 Uiso 1 1 calc R . .
C9 C 0.6522(3) 0.4890(5) 0.29471(15) 0.0543(12) Uani 1 1 d . . .
C10 C 0.7155(3) 0.5638(6) 0.33343(17) 0.0631(13) Uani 1 1 d . . .
H10 H 0.7668 0.5177 0.3553 0.076 Uiso 1 1 calc R . .
C11 C 0.7042(3) 0.7020(6) 0.34006(16) 0.0686(14) Uani 1 1 d . . .
H11 H 0.7471 0.7505 0.3670 0.082 Uiso 1 1 calc R . .
C12 C 0.6309(3) 0.7728(5) 0.30793(16) 0.0587(12) Uani 1 1 d . . .
H12 H 0.6238 0.8690 0.3130 0.070 Uiso 1 1 calc R . .
N5 N 0.4027(2) 0.9566(4) -0.05007(11) 0.0473(9) Uani 1 1 d U . .
N6 N 0.4261(2) 1.0882(4) -0.05637(12) 0.0552(10) Uani 1 1 d U . .
H6N H 0.4078 1.1605 -0.0419 0.066 Uiso 1 1 calc R . .
N7 N 0.3546(2) 0.3059(4) -0.00308(13) 0.0536(10) Uani 1 1 d . . .
N8 N 0.3265(2) 0.2702(4) 0.03937(14) 0.0591(10) Uani 1 1 d . . .
H8N H 0.3176 0.1848 0.0483 0.071 Uiso 1 1 calc R . .
C13 C 0.4810(3) 1.0944(5) -0.08767(16) 0.0598(13) Uani 1 1 d . . .
H13 H 0.5058 1.1761 -0.0981 0.072 Uiso 1 1 calc R . .
C14 C 0.4948(3) 0.9623(5) -0.10185(16) 0.0577(13) Uani 1 1 d . . .
H14 H 0.5310 0.9335 -0.1237 0.069 Uiso 1 1 calc R . .
C15 C 0.4448(2) 0.8787(4) -0.07757(14) 0.0435(10) Uani 1 1 d . . .
C16 C 0.3145(3) 0.3829(5) 0.06558(18) 0.0656(13) Uani 1 1 d . . .
H16 H 0.2950 0.3838 0.0966 0.079 Uiso 1 1 calc R . .
C17 C 0.3348(3) 0.4972(4) 0.04045(16) 0.0593(13) Uani 1 1 d . . .
H17 H 0.3324 0.5915 0.0501 0.071 Uiso 1 1 calc R . .
C18 C 0.3597(2) 0.4448(5) -0.00245(15) 0.0470(11) Uani 1 1 d . . .
C19 C 0.4312(2) 0.7291(4) -0.08021(14) 0.0428(11) Uani 1 1 d . . .
C20 C 0.4065(2) 0.6587(5) -0.04049(14) 0.0451(11) Uani 1 1 d . . .
H20 H 0.4035 0.7077 -0.0100 0.054 Uiso 1 1 calc R . .
C21 C 0.3860(2) 0.5177(5) -0.04451(14) 0.0454(11) Uani 1 1 d . . .
C22 C 0.3915(3) 0.4477(4) -0.08887(15) 0.0576(12) Uani 1 1 d . . .
H22 H 0.3770 0.3520 -0.0925 0.069 Uiso 1 1 calc R . .
C23 C 0.4178(3) 0.5153(5) -0.12810(16) 0.0612(13) Uani 1 1 d . . .
H23 H 0.4219 0.4658 -0.1583 0.073 Uiso 1 1 calc R . .
C24 C 0.4382(3) 0.6546(5) -0.12351(16) 0.0563(12) Uani 1 1 d . . .
H24 H 0.4573 0.7000 -0.1504 0.068 Uiso 1 1 calc R . .
N9 N 0.2523(2) 0.9936(4) 0.03409(12) 0.0543(10) Uani 1 1 d . . .
N10 N 0.2598(2) 0.9003(4) -0.00243(13) 0.0558(10) Uani 1 1 d . . .
H10N H 0.3042 0.8993 -0.0174 0.067 Uiso 1 1 calc R . .
N11 N 0.3485(2) 1.2288(4) 0.20817(13) 0.0548(10) Uani 1 1 d . . .
N12 N 0.3977(2) 1.3118(4) 0.24618(14) 0.0659(11) Uani 1 1 d . . .
H12N H 0.4569 1.3050 0.2595 0.079 Uiso 1 1 calc R . .
C25 C 0.1914(3) 0.8100(4) -0.01294(16) 0.0622(13) Uani 1 1 d . . .
H25 H 0.1825 0.7357 -0.0373 0.075 Uiso 1 1 calc R . .
C26 C 0.1361(3) 0.8442(5) 0.01784(17) 0.0625(13) Uani 1 1 d . . .
H26 H 0.0820 0.7989 0.0194 0.075 Uiso 1 1 calc R . .
C27 C 0.1760(2) 0.9579(5) 0.04582(15) 0.0505(12) Uani 1 1 d . . .
C28 C 0.3462(3) 1.4061(6) 0.26154(19) 0.0864(17) Uani 1 1 d . . .
H28 H 0.3660 1.4746 0.2879 0.104 Uiso 1 1 calc R . .
C29 C 0.2581(3) 1.3830(6) 0.23092(18) 0.0838(17) Uani 1 1 d . . .
H29 H 0.2055 1.4336 0.2319 0.101 Uiso 1 1 calc R . .
C30 C 0.2619(3) 1.2721(5) 0.19886(16) 0.0603(13) Uani 1 1 d U . .
C31 C 0.1482(3) 1.0414(4) 0.08532(15) 0.0523(12) Uani 1 1 d U . .
C32 C 0.2124(3) 1.1169(4) 0.12171(15) 0.0547(12) Uani 1 1 d U . .
H32 H 0.2739 1.1121 0.1210 0.066 Uiso 1 1 calc R . .
C33 C 0.1905(2) 1.1998(5) 0.15937(14) 0.0547(12) Uani 1 1 d U . .
C34 C 0.0985(3) 1.2105(5) 0.15760(16) 0.0673(14) Uani 1 1 d . . .
H34 H 0.0807 1.2697 0.1816 0.081 Uiso 1 1 calc R . .
C35 C 0.0342(3) 1.1363(5) 0.12164(17) 0.0735(15) Uani 1 1 d . . .
H35 H -0.0276 1.1430 0.1215 0.088 Uiso 1 1 calc R . .
C36 C 0.0576(3) 1.0521(5) 0.08558(16) 0.0679(14) Uani 1 1 d . . .
H36 H 0.0121 1.0013 0.0609 0.081 Uiso 1 1 calc R . .
O1 O -0.0039(8) 0.6801(12) 0.0950(5) 0.134(4) Uani 0.548(6) 1 d PDU A 1
C37 C -0.0959(10) 0.673(2) 0.0963(6) 0.124(5) Uani 0.548(6) 1 d PDU A 1
H37A H -0.1271 0.5988 0.0721 0.149 Uiso 0.548(6) 1 calc PR A 1
H37B H -0.0974 0.6475 0.1321 0.149 Uiso 0.548(6) 1 calc PR A 1
C38 C -0.1433(18) 0.798(3) 0.0819(13) 0.113(6) Uani 0.548(6) 1 d PDU A 1
H38A H -0.2059 0.7863 0.0835 0.170 Uiso 0.548(6) 1 calc PR A 1
H38B H -0.1434 0.8223 0.0461 0.170 Uiso 0.548(6) 1 calc PR A 1
H38C H -0.1136 0.8711 0.1061 0.170 Uiso 0.548(6) 1 calc PR A 1
C39 C 0.0517(9) 0.5805(15) 0.1225(6) 0.166(6) Uani 0.548(6) 1 d PDU A 1
H39A H 0.0308 0.4893 0.1067 0.199 Uiso 0.548(6) 1 calc PR A 1
H39B H 0.0470 0.5799 0.1589 0.199 Uiso 0.548(6) 1 calc PR A 1
C40 C 0.1443(7) 0.5986(13) 0.1237(6) 0.166(7) Uani 0.548(6) 1 d PDU A 1
H40A H 0.1499 0.5967 0.0878 0.248 Uiso 0.548(6) 1 calc PR A 1
H40B H 0.1807 0.5237 0.1441 0.248 Uiso 0.548(6) 1 calc PR A 1
H40C H 0.1661 0.6878 0.1400 0.248 Uiso 0.548(6) 1 calc PR A 1
O1' O -0.0281(8) 0.6316(16) 0.0651(5) 0.113(4) Uani 0.452(6) 1 d PDU A 2
C37' C -0.1156(12) 0.659(3) 0.0710(10) 0.152(7) Uani 0.452(6) 1 d PDU A 2
H37C H -0.1627 0.6244 0.0400 0.182 Uiso 0.452(6) 1 calc PR A 2
H37D H -0.1230 0.6113 0.1025 0.182 Uiso 0.452(6) 1 calc PR A 2
C38' C -0.127(2) 0.801(3) 0.0760(18) 0.130(10) Uani 0.452(6) 1 d PDU A 2
H38D H -0.1848 0.8194 0.0832 0.195 Uiso 0.452(6) 1 calc PR A 2
H38E H -0.1253 0.8478 0.0434 0.195 Uiso 0.452(6) 1 calc PR A 2
H38F H -0.0771 0.8370 0.1050 0.195 Uiso 0.452(6) 1 calc PR A 2
C39' C -0.0137(11) 0.4997(17) 0.0522(10) 0.184(8) Uani 0.452(6) 1 d PDU A 2
H39C H -0.0585 0.4777 0.0184 0.221 Uiso 0.452(6) 1 calc PR A 2
H39D H -0.0261 0.4375 0.0790 0.221 Uiso 0.452(6) 1 calc PR A 2
C40' C 0.0747(9) 0.4676(15) 0.0474(8) 0.167(9) Uani 0.452(6) 1 d PDU A 2
H40D H 0.0804 0.3672 0.0440 0.251 Uiso 0.452(6) 1 calc PR A 2
H40E H 0.1208 0.5001 0.0787 0.251 Uiso 0.452(6) 1 calc PR A 2
H40F H 0.0835 0.5136 0.0163 0.251 Uiso 0.452(6) 1 calc PR A 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
N1 0.039(2) 0.098(3) 0.0306(19) -0.004(2) 0.0101(17) 0.005(2)
N2 0.042(2) 0.092(3) 0.044(2) 0.008(2) 0.0173(18) 0.004(2)
N3 0.043(2) 0.077(3) 0.0411(19) -0.014(2) 0.0056(18) -0.003(2)
N4 0.052(2) 0.080(3) 0.053(2) -0.020(2) 0.010(2) -0.002(2)
C1 0.047(3) 0.090(4) 0.043(3) -0.002(3) 0.002(2) -0.014(3)
C2 0.044(3) 0.077(4) 0.043(3) -0.003(3) 0.000(2) -0.002(3)
C3 0.050(3) 0.076(4) 0.033(2) -0.013(3) 0.021(2) -0.005(3)
C4 0.049(3) 0.116(5) 0.074(3) -0.039(4) 0.019(3) 0.004(3)
C5 0.036(3) 0.112(5) 0.068(3) -0.035(3) 0.004(3) 0.002(3)
C6 0.038(3) 0.077(4) 0.041(2) -0.017(3) 0.006(2) -0.001(3)
C7 0.037(2) 0.089(4) 0.033(2) -0.011(3) 0.008(2) 0.001(3)
C8 0.039(3) 0.078(4) 0.037(2) -0.011(3) 0.011(2) -0.003(3)
C9 0.040(3) 0.090(4) 0.033(2) -0.016(3) 0.008(2) -0.009(3)
C10 0.038(3) 0.093(4) 0.049(3) -0.020(3) -0.002(2) 0.002(3)
C11 0.040(3) 0.111(5) 0.042(3) -0.021(3) -0.010(2) 0.001(3)
C12 0.052(3) 0.080(4) 0.040(2) -0.018(3) 0.005(2) 0.001(3)
N5 0.050(2) 0.057(3) 0.0330(19) 0.0119(18) 0.0080(17) -0.0097(19)
N6 0.048(2) 0.071(3) 0.047(2) 0.011(2) 0.0136(18) -0.005(2)
N7 0.043(2) 0.068(3) 0.052(2) 0.025(2) 0.0173(18) -0.006(2)
N8 0.051(2) 0.064(3) 0.066(3) 0.025(2) 0.021(2) -0.008(2)
C13 0.046(3) 0.077(4) 0.059(3) 0.028(3) 0.020(2) -0.002(3)
C14 0.044(3) 0.081(4) 0.055(3) 0.019(3) 0.024(2) 0.001(3)
C15 0.037(2) 0.060(3) 0.032(2) 0.016(2) 0.0080(19) 0.000(2)
C16 0.073(3) 0.072(4) 0.061(3) 0.008(3) 0.034(3) -0.006(3)
C17 0.072(3) 0.059(3) 0.051(3) 0.007(3) 0.024(3) -0.013(2)
C18 0.039(2) 0.058(3) 0.043(2) 0.014(2) 0.011(2) -0.005(2)
C19 0.030(2) 0.066(3) 0.031(2) 0.016(2) 0.0068(18) 0.001(2)
C20 0.027(2) 0.073(3) 0.031(2) 0.006(2) 0.0015(18) -0.009(2)
C21 0.037(2) 0.064(3) 0.034(2) 0.007(2) 0.009(2) -0.005(2)
C22 0.065(3) 0.065(3) 0.046(3) 0.013(2) 0.021(2) -0.002(2)
C23 0.071(3) 0.069(4) 0.049(3) 0.007(3) 0.027(3) 0.001(3)
C24 0.048(3) 0.081(4) 0.043(3) 0.019(3) 0.018(2) 0.002(3)
N9 0.046(2) 0.082(3) 0.0393(19) 0.010(2) 0.0182(18) -0.0010(19)
N10 0.042(2) 0.083(3) 0.045(2) 0.016(2) 0.0153(18) -0.014(2)
N11 0.042(2) 0.084(3) 0.0358(19) -0.003(2) 0.0052(17) -0.006(2)
N12 0.039(2) 0.106(3) 0.053(2) -0.014(2) 0.014(2) -0.007(2)
C25 0.048(3) 0.082(4) 0.051(3) 0.005(3) 0.005(2) -0.023(3)
C26 0.044(3) 0.089(4) 0.052(3) 0.017(3) 0.009(2) -0.026(3)
C27 0.029(2) 0.084(4) 0.036(2) 0.015(3) 0.004(2) -0.010(2)
C28 0.052(3) 0.141(5) 0.068(3) -0.032(3) 0.021(3) -0.002(3)
C29 0.052(3) 0.143(5) 0.059(3) -0.013(4) 0.022(3) 0.012(3)
C30 0.048(3) 0.101(4) 0.039(2) 0.010(3) 0.023(2) 0.008(3)
C31 0.033(2) 0.087(3) 0.033(2) 0.015(2) 0.002(2) -0.019(2)
C32 0.035(2) 0.093(4) 0.040(2) 0.018(2) 0.016(2) -0.001(2)
C33 0.036(2) 0.097(4) 0.031(2) 0.016(2) 0.010(2) -0.002(2)
C34 0.038(3) 0.128(4) 0.038(2) 0.016(3) 0.016(2) -0.001(3)
C35 0.034(2) 0.141(5) 0.045(3) 0.020(3) 0.010(2) -0.005(3)
C36 0.032(2) 0.130(4) 0.039(2) 0.015(3) 0.007(2) -0.018(3)
O1 0.098(7) 0.164(10) 0.143(10) 0.079(7) 0.039(7) 0.001(6)
C37 0.113(9) 0.190(13) 0.084(9) 0.021(10) 0.052(9) -0.005(9)
C38 0.071(9) 0.201(14) 0.067(9) 0.018(11) 0.016(10) -0.031(7)
C39 0.135(9) 0.205(15) 0.155(13) 0.091(11) 0.038(11) 0.025(9)
C40 0.104(7) 0.196(14) 0.180(14) 0.127(12) 0.013(10) 0.013(9)
O1' 0.070(6) 0.161(10) 0.109(9) -0.014(8) 0.025(6) -0.011(7)
C37' 0.067(9) 0.184(12) 0.191(19) -0.015(16) 0.014(11) 0.004(11)
C38' 0.084(16) 0.181(13) 0.14(2) 0.022(16) 0.058(13) -0.005(12)
C39' 0.100(11) 0.180(14) 0.27(2) -0.029(16) 0.041(13) 0.012(12)
C40' 0.119(12) 0.160(13) 0.26(2) 0.083(15) 0.123(16) 0.029(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
N1 C3 1.340(5) . ?
N1 N2 1.359(4) . ?
N2 C1 1.346(5) . ?
N2 H2N 0.8800 . ?
N3 C6 1.335(5) . ?
N3 N4 1.357(4) . ?
N4 C4 1.339(5) . ?
N4 H4N 0.8800 . ?
C1 C2 1.368(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.404(5) . ?
C2 H2 0.9500 . ?
C3 C7 1.474(6) . ?
C4 C5 1.368(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(5) . ?
C5 H5 0.9500 . ?
C6 C9 1.451(5) . ?
C7 C8 1.377(5) . ?
C7 C12 1.386(5) . ?
C8 C9 1.396(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.401(5) . ?
C10 C11 1.364(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
N5 C15 1.334(4) . ?
N5 N6 1.344(4) . ?
N6 C13 1.339(4) . ?
N6 H6N 0.8800 . ?
N7 C18 1.343(4) . ?
N7 N8 1.358(4) . ?
N8 C16 1.332(5) . ?
N8 H8N 0.8800 . ?
C13 C14 1.364(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(5) . ?
C14 H14 0.9500 . ?
C15 C19 1.459(5) . ?
C16 C17 1.370(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(5) . ?
C17 H17 0.9500 . ?
C18 C21 1.468(5) . ?
C19 C24 1.385(5) . ?
C19 C20 1.393(4) . ?
C20 C21 1.395(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.380(5) . ?
C22 C23 1.381(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
N9 C27 1.338(4) . ?
N9 N10 1.352(4) . ?
N10 C25 1.333(4) . ?
N10 H10N 0.8800 . ?
N11 N12 1.343(4) . ?
N11 C30 1.349(4) . ?
N12 C28 1.341(5) . ?
N12 H12N 0.8800 . ?
C25 C26 1.372(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.370(5) . ?
C26 H26 0.9500 . ?
C27 C31 1.477(5) . ?
C28 C29 1.388(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.379(6) . ?
C29 H29 0.9500 . ?
C30 C33 1.465(5) . ?
C31 C32 1.380(5) . ?
C31 C36 1.395(5) . ?
C32 C33 1.392(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.404(5) . ?
C34 C35 1.369(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.378(6) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
O1 C39 1.355(11) . ?
O1 C37 1.423(11) . ?
C37 C38 1.403(13) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.422(11) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
O1' C39' 1.354(13) . ?
O1' C37' 1.420(12) . ?
C37' C38' 1.393(16) . ?
C37' H37C 0.9900 . ?
C37' H37D 0.9900 . ?
C38' H38D 0.9800 . ?
C38' H38E 0.9800 . ?
C38' H38F 0.9800 . ?
C39' C40' 1.431(13) . ?
C39' H39C 0.9900 . ?
C39' H39D 0.9900 . ?
C40' H40D 0.9800 . ?
C40' H40E 0.9800 . ?
C40' H40F 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 N1 N2 105.2(4) . . ?
C1 N2 N1 111.7(4) . . ?
C1 N2 H2N 124.1 . . ?
N1 N2 H2N 124.1 . . ?
C6 N3 N4 104.3(3) . . ?
C4 N4 N3 112.2(4) . . ?
C4 N4 H4N 123.9 . . ?
N3 N4 H4N 123.9 . . ?
N2 C1 C2 107.1(4) . . ?
N2 C1 H1 126.4 . . ?
C2 C1 H1 126.4 . . ?
C1 C2 C3 105.7(4) . . ?
C1 C2 H2 127.2 . . ?
C3 C2 H2 127.2 . . ?
N1 C3 C2 110.3(4) . . ?
N1 C3 C7 120.3(4) . . ?
C2 C3 C7 129.3(5) . . ?
N4 C4 C5 107.0(4) . . ?
N4 C4 H4 126.5 . . ?
C5 C4 H4 126.5 . . ?
C4 C5 C6 105.1(4) . . ?
C4 C5 H5 127.5 . . ?
C6 C5 H5 127.5 . . ?
N3 C6 C5 111.4(4) . . ?
N3 C6 C9 119.4(4) . . ?
C5 C6 C9 129.2(4) . . ?
C8 C7 C12 118.6(4) . . ?
C8 C7 C3 120.4(4) . . ?
C12 C7 C3 121.0(5) . . ?
C7 C8 C9 122.6(4) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
C8 C9 C10 117.1(4) . . ?
C8 C9 C6 120.9(4) . . ?
C10 C9 C6 121.9(5) . . ?
C11 C10 C9 120.8(5) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.9(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C11 119.9(4) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C15 N5 N6 106.2(3) . . ?
C13 N6 N5 110.9(3) . . ?
C13 N6 H6N 124.6 . . ?
N5 N6 H6N 124.6 . . ?
C18 N7 N8 105.9(3) . . ?
C16 N8 N7 110.4(3) . . ?
C16 N8 H8N 124.8 . . ?
N7 N8 H8N 124.8 . . ?
N6 C13 C14 107.6(4) . . ?
N6 C13 H13 126.2 . . ?
C14 C13 H13 126.2 . . ?
C13 C14 C15 105.5(4) . . ?
C13 C14 H14 127.3 . . ?
C15 C14 H14 127.3 . . ?
N5 C15 C14 109.9(4) . . ?
N5 C15 C19 120.0(3) . . ?
C14 C15 C19 130.0(4) . . ?
N8 C16 C17 108.7(4) . . ?
N8 C16 H16 125.7 . . ?
C17 C16 H16 125.7 . . ?
C16 C17 C18 104.8(4) . . ?
C16 C17 H17 127.6 . . ?
C18 C17 H17 127.6 . . ?
N7 C18 C17 110.2(3) . . ?
N7 C18 C21 119.8(4) . . ?
C17 C18 C21 130.0(4) . . ?
C24 C19 C20 118.3(4) . . ?
C24 C19 C15 120.8(3) . . ?
C20 C19 C15 120.9(4) . . ?
C19 C20 C21 121.5(4) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 118.5(3) . . ?
C22 C21 C18 120.6(4) . . ?
C20 C21 C18 120.9(4) . . ?
C21 C22 C23 120.8(4) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 120.1(4) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C19 120.8(4) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
C27 N9 N10 104.4(3) . . ?
C25 N10 N9 111.5(3) . . ?
C25 N10 H10N 124.2 . . ?
N9 N10 H10N 124.2 . . ?
N12 N11 C30 105.7(3) . . ?
C28 N12 N11 112.2(3) . . ?
C28 N12 H12N 123.9 . . ?
N11 N12 H12N 123.9 . . ?
N10 C25 C26 107.4(4) . . ?
N10 C25 H25 126.3 . . ?
C26 C25 H25 126.3 . . ?
C27 C26 C25 105.0(3) . . ?
C27 C26 H26 127.5 . . ?
C25 C26 H26 127.5 . . ?
N9 C27 C26 111.6(4) . . ?
N9 C27 C31 118.0(4) . . ?
C26 C27 C31 130.4(4) . . ?
N12 C28 C29 105.8(4) . . ?
N12 C28 H28 127.1 . . ?
C29 C28 H28 127.1 . . ?
C30 C29 C28 106.5(4) . . ?
C30 C29 H29 126.7 . . ?
C28 C29 H29 126.7 . . ?
N11 C30 C29 109.7(4) . . ?
N11 C30 C33 119.0(4) . . ?
C29 C30 C33 131.3(4) . . ?
C32 C31 C36 118.3(4) . . ?
C32 C31 C27 119.6(3) . . ?
C36 C31 C27 121.9(4) . . ?
C31 C32 C33 122.6(4) . . ?
C31 C32 H32 118.7 . . ?
C33 C32 H32 118.7 . . ?
C32 C33 C34 117.4(4) . . ?
C32 C33 C30 120.4(3) . . ?
C34 C33 C30 122.2(4) . . ?
C35 C34 C33 120.5(4) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 121.1(4) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 H35 119.4 . . ?
C35 C36 C31 120.0(4) . . ?
C35 C36 H36 120.0 . . ?
C31 C36 H36 120.0 . . ?
C39 O1 C37 115.6(10) . . ?
C38 C37 O1 113.2(14) . . ?
C38 C37 H37A 108.9 . . ?
O1 C37 H37A 108.9 . . ?
C38 C37 H37B 108.9 . . ?
O1 C37 H37B 108.9 . . ?
H37A C37 H37B 107.7 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O1 C39 C40 113.6(11) . . ?
O1 C39 H39A 108.8 . . ?
C40 C39 H39A 108.8 . . ?
O1 C39 H39B 108.8 . . ?
C40 C39 H39B 108.8 . . ?
H39A C39 H39B 107.7 . . ?
C39' O1' C37' 115.6(14) . . ?
C38' C37' O1' 109.8(17) . . ?
C38' C37' H37C 109.7 . . ?
O1' C37' H37C 109.7 . . ?
C38' C37' H37D 109.7 . . ?
O1' C37' H37D 109.7 . . ?
H37C C37' H37D 108.2 . . ?
C37' C38' H38D 109.5 . . ?
C37' C38' H38E 109.5 . . ?
H38D C38' H38E 109.5 . . ?
C37' C38' H38F 109.5 . . ?
H38D C38' H38F 109.5 . . ?
H38E C38' H38F 109.5 . . ?
O1' C39' C40' 116.9(14) . . ?
O1' C39' H39C 108.1 . . ?
C40' C39' H39C 108.1 . . ?
O1' C39' H39D 108.1 . . ?
C40' C39' H39D 108.1 . . ?
H39C C39' H39D 107.3 . . ?
C39' C40' H40D 109.5 . . ?
C39' C40' H40E 109.5 . . ?
H40D C40' H40E 109.5 . . ?
C39' C40' H40F 109.5 . . ?
H40D C40' H40F 109.5 . . ?
H40E C40' H40F 109.5 . . ?

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
C3 N1 N2 C1 0.2(4) . . . . ?
C6 N3 N4 C4 -0.5(4) . . . . ?
N1 N2 C1 C2 0.4(4) . . . . ?
N2 C1 C2 C3 -0.8(4) . . . . ?
N2 N1 C3 C2 -0.7(4) . . . . ?
N2 N1 C3 C7 -177.0(3) . . . . ?
C1 C2 C3 N1 0.9(4) . . . . ?
C1 C2 C3 C7 176.8(3) . . . . ?
N3 N4 C4 C5 1.1(5) . . . . ?
N4 C4 C5 C6 -1.2(5) . . . . ?
N4 N3 C6 C5 -0.3(4) . . . . ?
N4 N3 C6 C9 -179.7(3) . . . . ?
C4 C5 C6 N3 0.9(5) . . . . ?
C4 C5 C6 C9 -179.7(4) . . . . ?
N1 C3 C7 C8 -175.6(3) . . . . ?
C2 C3 C7 C8 8.9(6) . . . . ?
N1 C3 C7 C12 3.0(5) . . . . ?
C2 C3 C7 C12 -172.6(3) . . . . ?
C12 C7 C8 C9 -0.8(5) . . . . ?
C3 C7 C8 C9 177.8(3) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C7 C8 C9 C6 -179.6(3) . . . . ?
N3 C6 C9 C8 -29.6(5) . . . . ?
C5 C6 C9 C8 151.2(4) . . . . ?
N3 C6 C9 C10 151.5(4) . . . . ?
C5 C6 C9 C10 -27.8(6) . . . . ?
C8 C9 C10 C11 1.7(5) . . . . ?
C6 C9 C10 C11 -179.3(4) . . . . ?
C9 C10 C11 C12 -1.3(6) . . . . ?
C8 C7 C12 C11 1.2(5) . . . . ?
C3 C7 C12 C11 -177.4(3) . . . . ?
C10 C11 C12 C7 -0.1(6) . . . . ?
C15 N5 N6 C13 0.7(4) . . . . ?
C18 N7 N8 C16 0.0(4) . . . . ?
N5 N6 C13 C14 -0.7(4) . . . . ?
N6 C13 C14 C15 0.4(5) . . . . ?
N6 N5 C15 C14 -0.5(4) . . . . ?
N6 N5 C15 C19 -178.1(3) . . . . ?
C13 C14 C15 N5 0.1(5) . . . . ?
C13 C14 C15 C19 177.4(4) . . . . ?
N7 N8 C16 C17 0.0(5) . . . . ?
N8 C16 C17 C18 0.0(5) . . . . ?
N8 N7 C18 C17 0.0(5) . . . . ?
N8 N7 C18 C21 -178.3(3) . . . . ?
C16 C17 C18 N7 0.0(5) . . . . ?
C16 C17 C18 C21 178.0(4) . . . . ?
N5 C15 C19 C24 151.3(4) . . . . ?
C14 C15 C19 C24 -25.9(6) . . . . ?
N5 C15 C19 C20 -25.5(5) . . . . ?
C14 C15 C19 C20 157.3(4) . . . . ?
C24 C19 C20 C21 -2.2(5) . . . . ?
C15 C19 C20 C21 174.6(3) . . . . ?
C19 C20 C21 C22 0.7(6) . . . . ?
C19 C20 C21 C18 -179.8(3) . . . . ?
N7 C18 C21 C22 10.4(6) . . . . ?
C17 C18 C21 C22 -167.5(4) . . . . ?
N7 C18 C21 C20 -169.2(4) . . . . ?
C17 C18 C21 C20 13.0(6) . . . . ?
C20 C21 C22 C23 0.8(6) . . . . ?
C18 C21 C22 C23 -178.8(4) . . . . ?
C21 C22 C23 C24 -0.6(7) . . . . ?
C22 C23 C24 C19 -1.1(6) . . . . ?
C20 C19 C24 C23 2.4(6) . . . . ?
C15 C19 C24 C23 -174.4(4) . . . . ?
C27 N9 N10 C25 -0.2(4) . . . . ?
C30 N11 N12 C28 0.0(4) . . . . ?
N9 N10 C25 C26 -0.1(4) . . . . ?
N10 C25 C26 C27 0.4(4) . . . . ?
N10 N9 C27 C26 0.4(4) . . . . ?
N10 N9 C27 C31 -180.0(3) . . . . ?
C25 C26 C27 N9 -0.5(5) . . . . ?
C25 C26 C27 C31 180.0(4) . . . . ?
N11 N12 C28 C29 -0.6(5) . . . . ?
N12 C28 C29 C30 1.0(5) . . . . ?
N12 N11 C30 C29 0.6(4) . . . . ?
N12 N11 C30 C33 -179.0(3) . . . . ?
C28 C29 C30 N11 -1.0(5) . . . . ?
C28 C29 C30 C33 178.6(4) . . . . ?
N9 C27 C31 C32 -23.2(5) . . . . ?
C26 C27 C31 C32 156.3(4) . . . . ?
N9 C27 C31 C36 153.6(4) . . . . ?
C26 C27 C31 C36 -26.9(6) . . . . ?
C36 C31 C32 C33 1.8(6) . . . . ?
C27 C31 C32 C33 178.8(3) . . . . ?
C31 C32 C33 C34 -3.3(6) . . . . ?
C31 C32 C33 C30 176.8(4) . . . . ?
N11 C30 C33 C32 -18.7(6) . . . . ?
C29 C30 C33 C32 161.8(4) . . . . ?
N11 C30 C33 C34 161.4(4) . . . . ?
C29 C30 C33 C34 -18.2(7) . . . . ?
C32 C33 C34 C35 3.1(6) . . . . ?
C30 C33 C34 C35 -177.0(4) . . . . ?
C33 C34 C35 C36 -1.5(7) . . . . ?
C34 C35 C36 C31 0.0(7) . . . . ?
C32 C31 C36 C35 -0.1(6) . . . . ?
C27 C31 C36 C35 -177.0(4) . . . . ?
C39 O1 C37 C38 161.4(19) . . . . ?
C37 O1 C39 C40 -175.1(14) . . . . ?
C39' O1' C37' C38' -171(3) . . . . ?
C37' O1' C39' C40' -178.3(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.914
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 0.914
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042

# Attachment 'B803855D_Rev_compound_2.cif'

data_werner10
_database_code_depnum_ccdc_archive 'CCDC 679322'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N4'
_chemical_formula_weight         210.24

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   C2/c

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

_cell_length_a                   10.4886(11)
_cell_length_b                   12.8375(13)
_cell_length_c                   15.7298(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.024(2)
_cell_angle_gamma                90.00
_cell_volume                     2078.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    183
_cell_measurement_reflns_used    1989
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      25.74

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      183
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart 1K CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9102
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2038
_reflns_number_gt                1520
_reflns_threshold_expression     >2sigma(I)

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

_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^)+(0.0558P)^2^+0.5815P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2038
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.03341(14) 0.29464(10) 0.37569(8) 0.0583(4) Uani 1 1 d . . .
H1N H 0.0929 0.2600 0.3573 0.070 Uiso 0.50 1 calc PR . .
N2 N -0.02965(15) 0.37757(11) 0.33535(9) 0.0675(4) Uani 1 1 d . . .
H2N H -0.0175 0.4049 0.2876 0.081 Uiso 0.50 1 calc PR . .
N3 N 0.13037(13) -0.10118(10) 0.73511(9) 0.0577(4) Uani 1 1 d . . .
H3N H 0.0530 -0.0838 0.7401 0.069 Uiso 0.50 1 calc PR . .
N4 N 0.20089(14) -0.17687(11) 0.78054(9) 0.0638(4) Uani 1 1 d . . .
H4N H 0.1768 -0.2163 0.8187 0.077 Uiso 0.50 1 calc PR . .
C1 C 0.14394(15) 0.02743(11) 0.62173(10) 0.0480(4) Uani 1 1 d . . .
C3 C 0.15831(17) 0.13935(12) 0.50104(11) 0.0592(4) Uani 1 1 d . . .
H3 H 0.2032 0.1597 0.4582 0.071 Uiso 1 1 calc R . .
C4 C 0.04204(15) 0.18875(11) 0.50668(10) 0.0505(4) Uani 1 1 d . . .
C5 C -0.02207(16) 0.15479(14) 0.57075(11) 0.0615(4) Uani 1 1 d . . .
H5 H -0.1000 0.1862 0.5763 0.074 Uiso 1 1 calc R . .
C6 C 0.02698(17) 0.07576(14) 0.62630(11) 0.0619(4) Uani 1 1 d . . .
H6 H -0.0193 0.0541 0.6680 0.074 Uiso 1 1 calc R . .
C7 C -0.01015(15) 0.27416(12) 0.44856(10) 0.0530(4) Uani 1 1 d . . .
C8 C -0.1055(2) 0.34664(15) 0.45566(13) 0.0772(6) Uani 1 1 d . . .
H8 H -0.1533 0.3521 0.4995 0.093 Uiso 1 1 calc R . .
C9 C -0.1139(2) 0.40931(16) 0.38281(13) 0.0817(6) Uani 1 1 d . . .
H9 H -0.1703 0.4653 0.3693 0.098 Uiso 1 1 calc R . .
C10 C 0.19826(15) -0.05661(11) 0.68082(10) 0.0496(4) Uani 1 1 d . . .
C11 C 0.31853(17) -0.10488(14) 0.69245(12) 0.0665(5) Uani 1 1 d . . .
H11 H 0.3868 -0.0905 0.6642 0.080 Uiso 1 1 calc R . .
C12 C 0.31425(19) -0.17956(15) 0.75572(13) 0.0741(5) Uani 1 1 d . . .
H12 H 0.3816 -0.2250 0.7775 0.089 Uiso 1 1 calc R . .
C2 C 0.20798(17) 0.06144(12) 0.55711(11) 0.0574(4) Uani 1 1 d . . .
H2 H 0.2863 0.0305 0.5519 0.069 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
N1 0.0688(9) 0.0502(7) 0.0551(8) -0.0032(6) 0.0100(7) 0.0022(7)
N2 0.0826(11) 0.0589(9) 0.0589(9) 0.0022(7) 0.0083(8) 0.0069(8)
N3 0.0605(9) 0.0536(8) 0.0613(8) 0.0011(7) 0.0178(7) -0.0032(7)
N4 0.0672(9) 0.0586(8) 0.0678(9) 0.0087(7) 0.0183(7) -0.0008(7)
C1 0.0494(9) 0.0421(8) 0.0516(9) -0.0068(6) 0.0075(7) -0.0066(7)
C3 0.0688(11) 0.0516(9) 0.0619(10) 0.0034(8) 0.0244(8) 0.0031(8)
C4 0.0559(9) 0.0441(8) 0.0504(9) -0.0081(7) 0.0073(7) -0.0027(7)
C5 0.0532(10) 0.0657(10) 0.0678(11) 0.0033(9) 0.0168(8) 0.0083(8)
C6 0.0579(10) 0.0681(10) 0.0633(10) 0.0075(9) 0.0207(8) 0.0018(9)
C7 0.0591(10) 0.0477(9) 0.0506(9) -0.0068(7) 0.0065(7) 0.0008(7)
C8 0.0901(14) 0.0755(12) 0.0689(12) 0.0059(10) 0.0221(10) 0.0287(11)
C9 0.0954(15) 0.0723(12) 0.0758(13) 0.0062(10) 0.0119(11) 0.0290(11)
C10 0.0528(9) 0.0454(8) 0.0505(8) -0.0049(7) 0.0098(7) -0.0068(7)
C11 0.0577(11) 0.0677(11) 0.0765(12) 0.0142(9) 0.0188(9) 0.0058(9)
C12 0.0657(12) 0.0732(12) 0.0846(13) 0.0149(10) 0.0175(10) 0.0122(9)
C2 0.0589(10) 0.0492(9) 0.0681(10) 0.0005(8) 0.0218(8) 0.0050(8)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.339(2) . ?
N1 N2 1.3464(18) . ?
N1 H1N 0.8600 . ?
N2 C9 1.325(2) . ?
N2 H2N 0.8600 . ?
N3 C10 1.3402(19) . ?
N3 N4 1.3416(19) . ?
N3 H3N 0.8600 . ?
N4 C12 1.321(2) . ?
N4 H4N 0.8600 . ?
C1 C6 1.389(2) . ?
C1 C2 1.391(2) . ?
C1 C10 1.466(2) . ?
C3 C2 1.369(2) . ?
C3 C4 1.392(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C4 C7 1.465(2) . ?
C5 C6 1.373(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.386(2) . ?
C8 C9 1.389(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.386(2) . ?
C11 C12 1.389(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C2 H2 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
C7 N1 N2 109.97(14) . . ?
C7 N1 H1N 125.0 . . ?
N2 N1 H1N 125.0 . . ?
C9 N2 N1 107.33(15) . . ?
C9 N2 H2N 126.3 . . ?
N1 N2 H2N 126.3 . . ?
C10 N3 N4 110.04(13) . . ?
C10 N3 H3N 125.0 . . ?
N4 N3 H3N 125.0 . . ?
C12 N4 N3 107.29(14) . . ?
C12 N4 H4N 126.4 . . ?
N3 N4 H4N 126.4 . . ?
C6 C1 C2 116.89(15) . . ?
C6 C1 C10 122.40(14) . . ?
C2 C1 C10 120.70(14) . . ?
C2 C3 C4 121.45(15) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 117.14(15) . . ?
C5 C4 C7 120.96(15) . . ?
C3 C4 C7 121.89(15) . . ?
C6 C5 C4 121.39(16) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 121.62(16) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
N1 C7 C8 107.87(15) . . ?
N1 C7 C4 122.24(14) . . ?
C8 C7 C4 129.89(16) . . ?
C7 C8 C9 104.77(18) . . ?
C7 C8 H8 127.6 . . ?
C9 C8 H8 127.6 . . ?
N2 C9 C8 110.06(17) . . ?
N2 C9 H9 125.0 . . ?
C8 C9 H9 125.0 . . ?
N3 C10 C11 107.83(14) . . ?
N3 C10 C1 121.92(14) . . ?
C11 C10 C1 130.25(15) . . ?
C10 C11 C12 104.47(16) . . ?
C10 C11 H11 127.8 . . ?
C12 C11 H11 127.8 . . ?
N4 C12 C11 110.37(16) . . ?
N4 C12 H12 124.8 . . ?
C11 C12 H12 124.8 . . ?
C3 C2 C1 121.50(15) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?

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
C7 N1 N2 C9 -0.28(19) . . . . ?
C10 N3 N4 C12 0.68(18) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C2 C3 C4 C7 178.27(15) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C7 C4 C5 C6 -179.10(15) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C2 C1 C6 C5 -1.2(2) . . . . ?
C10 C1 C6 C5 179.60(15) . . . . ?
N2 N1 C7 C8 0.12(19) . . . . ?
N2 N1 C7 C4 -179.17(13) . . . . ?
C5 C4 C7 N1 -165.90(15) . . . . ?
C3 C4 C7 N1 15.1(2) . . . . ?
C5 C4 C7 C8 15.0(3) . . . . ?
C3 C4 C7 C8 -164.04(18) . . . . ?
N1 C7 C8 C9 0.1(2) . . . . ?
C4 C7 C8 C9 179.29(17) . . . . ?
N1 N2 C9 C8 0.3(2) . . . . ?
C7 C8 C9 N2 -0.3(2) . . . . ?
N4 N3 C10 C11 -0.71(18) . . . . ?
N4 N3 C10 C1 178.77(13) . . . . ?
C6 C1 C10 N3 9.0(2) . . . . ?
C2 C1 C10 N3 -170.11(14) . . . . ?
C6 C1 C10 C11 -171.60(17) . . . . ?
C2 C1 C10 C11 9.3(2) . . . . ?
N3 C10 C11 C12 0.46(19) . . . . ?
C1 C10 C11 C12 -178.97(16) . . . . ?
N3 N4 C12 C11 -0.4(2) . . . . ?
C10 C11 C12 N4 0.0(2) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
C10 C1 C2 C3 179.60(15) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.028