# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is © The Royal Society of Chemistry 2001
# CCDC Number: 1145/268

data_global

publ_contact_author
;
Prof. J. D. Wallis
;
_publ_contact_author_email       john.wallis@ntu.ac.uk
_publ_contact_author_fax         0115-948-6636
_publ_contact_author_phone       0115-848-3149

_publ_requested_journal           'J. Mater. Chem.'

_publ_section_title
;
Synthesis, characterisation and structure-property analysis of 
derivatives
of the non-linear optical material 5-nitro-N-(1-phenylethyl)-2-
pyridinamine.


;
loop_
_publ_author_name
_publ_author_address
'John D. Wallis'
;
Department of Chemistry and Physics
Nottingham Trent University
Clifton Lane
Nottingham
UK NG11 8NS
;

#TEXT

_publ_section_references
;
Darr,  J.A., Drake, S.R., Hursthouse, M.B. & Malik, K.M.A. (1993).
Inorg. Chem., 32, 5704-5708.

Karaoulov, A. I. (1992). ABSMAD. Program for FAST Data Processing.
University of Wales, Cardiff, Wales.

Nonius (1997a). Kappa-CCD Control Software. Nonius BV, Delft, The
Netherlands.

Nonius (1997b). Kappa-CCD DENZO Processing Software, Nonius BV, Delft,
The Netherlands. 

Pflugrath, J.W. & Messerschmidt, A. (1989) MADNES version 11-09-
89, Program for Control of Data Collection with Enraf-Nonius FAST
X-ray Diffractometer, Enraf-Nonius, Delft, The Netherlands.  

Sheldrick, G.M. (1990). Acta Cryst. A46, 467-473.

Sheldrick, G.M. (1993). SHELXL-93 Program for the Refinement of Crystal 
Structures, University of G\"ottingen, Germany.
;

#DATA

data_compound_(S)-2 
 
_audit_creation_method            SHELXL
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C14 H15 N3 O2'
_chemical_formula_weight          257.29
_chemical_melting_point           318-319
_chemical_compound_source         ?
 
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    P212121
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 
_cell_length_a                    5.481(4)
_cell_length_b                    6.791(8)
_cell_length_c                    35.877(29)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1335.4(21)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     250
_cell_measurement_theta_min       2.27
_cell_measurement_theta_max       24.94
 
_exptl_crystal_description        rod
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.28
_exptl_crystal_size_mid           0.22
_exptl_crystal_size_min           0.18
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.280
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              544
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'rotating anode source' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        'Delft Instruments FAST-TV area-
detector'
_diffrn_measurement_method        'Darr et al. (1993)'
_diffrn_standards_number          'not measured'
_diffrn_standards_interval_count  'not measured'
_diffrn_standards_interval_time    'not measured'
_diffrn_standards_decay_%          'not measured'
_diffrn_reflns_number             4474
_diffrn_reflns_av_R_equivalents   0.1208
_diffrn_reflns_av_sigmaI/netI     0.0966
_diffrn_reflns_limit_h_min        -5
_diffrn_reflns_limit_h_max        4
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -38
_diffrn_reflns_limit_l_max        39
_diffrn_reflns_theta_min          2.27
_diffrn_reflns_theta_max          24.94
_reflns_number_total              1842
_reflns_number_observed           1562
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection       'MADNES (Pflugrath & 
Messerschmidt,1989)' 
_computing_cell_refinement        'REFINE (incorporated in MADNES)' 
_computing_data_reduction         'ABSMAD (Karaulov, 1991)'
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     ?
_computing_publication_material   'SHELXL-93 (Sheldrick, 1993)'  


_refine_special_details
;
 Refinement on F^2^ for ALL reflections except for 22 with very negative
F^2^
 or flagged by the user for potential systematic errors.  Weighted R-
factors
 wR and all goodnesses 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 observed
criterion
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.1099P)^2^+0.0318P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    difmap
_refine_ls_hydrogen_treatment     refall
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    -1.30(330)
_refine_ls_number_reflns          1820
_refine_ls_number_parameters      232
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0765
_refine_ls_R_factor_obs           0.0573
_refine_ls_wR_factor_all          0.1794
_refine_ls_wR_factor_obs          0.1718
_refine_ls_goodness_of_fit_all    1.234
_refine_ls_goodness_of_fit_obs    1.318
_refine_ls_restrained_S_all       1.254
_refine_ls_restrained_S_obs       1.318
_refine_ls_shift/esd_max          -0.002
_refine_ls_shift/esd_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_thermal_displace_type
 _atom_site_occupancy
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_group
O1 O 0.4808(7) 0.8553(5) 0.03156(8) 0.0502(9) Uani 1 d . .
O2 O 0.2310(9) 0.8333(5) 0.07802(12) 0.0746(13) Uani 1 d . .
N1 N 0.5095(7) 0.3103(5) 0.11124(9) 0.0315(8) Uani 1 d . .
N2 N 0.8045(7) 0.0703(5) 0.10626(9) 0.0318(8) Uani 1 d . .
N5 N 0.3973(7) 0.7669(5) 0.05840(10) 0.0398(10) Uani 1 d . .
C2 C 0.7008(8) 0.2361(6) 0.09211(10) 0.0278(9) Uani 1 d . .
C3 C 0.7973(8) 0.3240(6) 0.05910(10) 0.0288(9) Uani 1 d . .
C4 C 0.6965(8) 0.5006(6) 0.04797(11) 0.0329(10) Uani 1 d . .
C5 C 0.5032(9) 0.5794(5) 0.06891(10) 0.0313(9) Uani 1 d . .
C6 C 0.4123(9) 0.4800(6) 0.09959(11) 0.0344(10) Uani 1 d . .
C7 C 0.7327(9) -0.0115(6) 0.14235(10) 0.0295(10) Uani 1 d . .
C8 C 0.8670(11) -0.2073(7) 0.14875(13) 0.0431(12) Uani 1 d . .
C31 C 0.9973(10) 0.2264(7) 0.03714(12) 0.0377(10) Uani 1 d . .
C1' C 0.7843(8) 0.1293(6) 0.17431(10) 0.0300(9) Uani 1 d . .
C2' C 0.6206(8) 0.1401(7) 0.20421(11) 0.0353(10) Uani 1 d . .
C3' C 0.6678(9) 0.2620(7) 0.23442(11) 0.0402(11) Uani 1 d . .
C4' C 0.8784(9) 0.3765(7) 0.23536(12) 0.0416(11) Uani 1 d . .
C5' C 1.0412(9) 0.3666(7) 0.20603(12) 0.0383(10) Uani 1 d . .
C6' C 0.9955(9) 0.2432(6) 0.17590(12) 0.0342(10) Uani 1 d . .
H2 H 0.9313(95) 0.0284(59) 0.0954(12) 0.026(11) Uiso 1 d . .
H4 H 0.7525(76) 0.5720(51) 0.0240(10) 0.019(9) Uiso 1 d . .
H6 H 0.2846(97) 0.5296(63) 0.1118(13) 0.037(12) Uiso 1 d . .
H71 H 0.5639(86) -0.0296(54) 0.1421(10) 0.022(10) Uiso 1 d . .
H81 H 1.0569(129) -0.1797(76) 0.1501(15) 0.059(16) Uiso 1 d . .
H82 H 0.8170(97) -0.2672(73) 0.1743(15) 0.051(14) Uiso 1 d . .
H83 H 0.8326(106) -0.2995(84) 0.1286(17) 0.060(15) Uiso 1 d . .
H311 H 1.0342(76) 0.3013(56) 0.0170(12) 0.023(10) Uiso 1 d . .
H312 H 1.1486(104) 0.2181(78) 0.0544(16) 0.059(16) Uiso 1 d . .
H313 H 0.9579(111) 0.0957(95) 0.0277(16) 0.065(17) Uiso 1 d . .
H21' H 0.4538(105) 0.0684(77) 0.2007(14) 0.055(15) Uiso 1 d . .
H31' H 0.5461(79) 0.2704(52) 0.2548(11) 0.022(9) Uiso 1 d . .
H41' H 0.9006(78) 0.4673(62) 0.2561(13) 0.031(11) Uiso 1 d . .
H51' H 1.1977(98) 0.4339(76) 0.2034(13) 0.049(13) Uiso 1 d . .
H61' H 1.0958(123) 0.2381(92) 0.1587(19) 0.072(19) Uiso 1 d . .
 
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 0.064(2) 0.047(2) 0.039(2) 0.0173(14) 0.001(2) 0.013(2)
O2 0.083(3) 0.063(2) 0.078(3) 0.026(2) 0.031(2) 0.046(2)
N1 0.029(2) 0.036(2) 0.030(2) 0.0022(13) 0.0037(15) 0.008(2)
N2 0.033(2) 0.037(2) 0.026(2) 0.0037(14) 0.004(2) 0.0128(15)
N5 0.045(3) 0.038(2) 0.036(2) 0.002(2) 0.000(2) 0.012(2)
C2 0.030(2) 0.031(2) 0.023(2) -0.0004(15) -0.001(2) 0.004(2)
C3 0.031(2) 0.032(2) 0.023(2) -0.002(2) -0.003(2) 0.005(2)
C4 0.039(3) 0.035(2) 0.025(2) 0.003(2) -0.003(2) 0.003(2)
C5 0.034(2) 0.028(2) 0.032(2) 0.003(2) -0.003(2) 0.009(2)
C6 0.032(3) 0.039(2) 0.032(2) 0.000(2) 0.003(2) 0.012(2)
C7 0.027(3) 0.032(2) 0.029(2) 0.006(2) 0.002(2) 0.004(2)
C8 0.064(4) 0.034(3) 0.032(2) 0.005(2) -0.001(2) 0.007(2)
C31 0.043(3) 0.042(3) 0.028(2) 0.006(2) 0.007(2) 0.007(2)
C1' 0.033(3) 0.031(2) 0.026(2) 0.0084(15) 0.000(2) 0.006(2)
C2' 0.032(3) 0.038(2) 0.036(2) 0.009(2) 0.005(2) 0.004(2)
C3' 0.041(3) 0.052(3) 0.028(2) -0.003(2) 0.006(2) 0.008(2)
C4' 0.048(3) 0.039(2) 0.038(2) -0.007(2) -0.007(2) 0.007(2)
C5' 0.033(3) 0.036(2) 0.047(3) 0.002(2) -0.005(2) 0.000(2)
C6' 0.033(3) 0.037(2) 0.033(2) 0.006(2) 0.005(2) 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
O1 N5 1.223(5) . ?
O2 N5 1.237(5) . ?
N1 C6 1.337(5) . ?
N1 C2 1.350(5) . ?
N2 C2 1.360(5) . ?
N2 C7 1.463(5) . ?
N5 C5 1.449(5) . ?
C2 C3 1.428(6) . ?
C3 C4 1.380(6) . ?
C3 C31 1.504(6) . ?
C4 C5 1.405(6) . ?
C5 C6 1.384(6) . ?
C7 C1' 1.520(6) . ?
C7 C8 1.537(6) . ?
C1' C6' 1.393(6) . ?
C1' C2' 1.400(6) . ?
C2' C3' 1.388(7) . ?
C3' C4' 1.392(7) . ?
C4' C5' 1.381(7) . ?
C5' C6' 1.390(6) . ?
 
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
C6 N1 C2 118.2(3) . . ?
C2 N2 C7 122.2(3) . . ?
O1 N5 O2 123.0(4) . . ?
O1 N5 C5 119.1(4) . . ?
O2 N5 C5 117.8(4) . . ?
N1 C2 N2 116.3(3) . . ?
N1 C2 C3 123.6(4) . . ?
N2 C2 C3 120.0(4) . . ?
C4 C3 C2 117.1(4) . . ?
C4 C3 C31 121.6(4) . . ?
C2 C3 C31 121.4(3) . . ?
C3 C4 C5 118.6(4) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 N5 119.4(4) . . ?
C4 C5 N5 119.8(3) . . ?
N1 C6 C5 121.7(4) . . ?
N2 C7 C1' 112.3(3) . . ?
N2 C7 C8 109.4(3) . . ?
C1' C7 C8 110.0(3) . . ?
C6' C1' C2' 118.2(4) . . ?
C6' C1' C7 122.3(4) . . ?
C2' C1' C7 119.5(4) . . ?
C3' C2' C1' 120.7(4) . . ?
C2' C3' C4' 120.4(4) . . ?
C5' C4' C3' 119.3(4) . . ?
C4' C5' C6' 120.4(4) . . ?
C5' C6' C1' 121.1(4) . . ?
 
_refine_diff_density_max    0.268
_refine_diff_density_min   -0.253
_refine_diff_density_rms    0.064

#===END

data_compound_5 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C14 H15 N3 O2' 
_chemical_formula_weight          257.29 
_chemical_melting_point           379-381 
_chemical_compound_source         ? 
 
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    P21 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
 
_cell_length_a                    11.4150(7) 
_cell_length_b                    10.6973(5) 
_cell_length_c                    16.935(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  102.638(9) 
_cell_angle_gamma                 90.00 
_cell_volume                      2017.8(3) 
_cell_formula_units_Z             6 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     250
_cell_measurement_theta_min       1.83 
_cell_measurement_theta_max       25.08 
 
_exptl_crystal_description        'thick plate' 
_exptl_crystal_colour             yellow 
_exptl_crystal_size_max           0.32 
_exptl_crystal_size_mid           0.28
_exptl_crystal_size_min           0.14 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.270 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              816 
_exptl_absorpt_coefficient_mu     0.087 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(2) 
_diffrn_radiation_wavelength      0.71069 
_diffrn_radiation_type            MoK\a  
_diffrn_radiation_source          'rotating anode source' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        'Delft Instruments FAST-TV area-
detector'
_diffrn_measurement_method        'Darr et al. (1993)'
_diffrn_standards_number          'not measured'
_diffrn_standards_interval_count  'not measured'
_diffrn_standards_interval_time    'not measured'
_diffrn_standards_decay_%          'not measured' 
_diffrn_reflns_number             9082 
_diffrn_reflns_av_R_equivalents   0.0693 
_diffrn_reflns_av_sigmaI/netI     0.0895 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          1.83 
_diffrn_reflns_theta_max          25.08 
_reflns_number_total              5847 
_reflns_number_observed           4322 
_reflns_observed_criterion        >2sigma(I) 

_computing_data_collection       'MADNES (Pflugrath & 
Messerschmidt,1989)' 
_computing_cell_refinement        'REFINE (incorporated in MADNES)' 
_computing_data_reduction         'ABSMAD (Karaulov, 1991)'
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     ?
_computing_publication_material   'SHELXL-93 (Sheldrick, 1993)'  

_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 124 with very 
negative
F^2^ 
 or flagged by the user for potential systematic errors.  Weighted R-
factors

 wR and all goodnesses 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 observed
criterion 
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+( 0.1134P)^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     riding 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    1.13(135) 
_refine_ls_number_reflns          5723 
_refine_ls_number_parameters      520 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0635 
_refine_ls_R_factor_obs           0.0501 
_refine_ls_wR_factor_all          0.1288 
_refine_ls_wR_factor_obs          0.1186 
_refine_ls_goodness_of_fit_all    0.661 
_refine_ls_goodness_of_fit_obs    0.713 
_refine_ls_restrained_S_all       0.659 
_refine_ls_restrained_S_obs       0.713 
_refine_ls_shift/esd_max          -0.092 
_refine_ls_shift/esd_mean         0.007 
 
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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
O1A O 0.9784(2) 0.8731(2) 0.4425(2) 0.0420(6) Uani 1 d . . 
O2A O 0.8522(2) 0.7376(2) 0.4702(2) 0.0443(7) Uani 1 d . . 
N1A N 0.7356(3) 0.9816(2) 0.6196(2) 0.0321(7) Uani 1 d . . 
N2A N 0.7582(3) 1.1640(3) 0.6916(2) 0.0379(7) Uani 1 d . . 
H2A H 0.6837(3) 1.1505(3) 0.6957(2) 0.046 Uiso 1 calc R . 
N5A N 0.9027(3) 0.8408(3) 0.4799(2) 0.0325(7) Uani 1 d . . 
C2A C 0.8038(3) 1.0852(3) 0.6442(2) 0.0287(8) Uani 1 d . . 
C3A C 0.9112(3) 1.1081(3) 0.6185(2) 0.0297(8) Uani 1 d . . 
H3A H 0.9602(3) 1.1776(3) 0.6390(2) 0.036 Uiso 1 calc R . 
C4A C 0.9437(3) 1.0296(3) 0.5639(2) 0.0303(8) Uani 1 d . . 
H4A H 1.0140(3) 1.0449(3) 0.5440(2) 0.036 Uiso 1 calc R . 
C5A C 0.8716(3) 0.9264(3) 0.5379(2) 0.0284(8) Uani 1 d . . 
C6A C 0.7702(3) 0.9052(3) 0.5676(2) 0.0289(8) Uani 1 d . . 
H6A H 0.7234(3) 0.8329(3) 0.5501(2) 0.035 Uiso 1 calc R . 
C7A C 0.8202(3) 1.2695(3) 0.7368(2) 0.0373(9) Uani 1 d . . 
H7A H 0.8763(3) 1.3059(3) 0.7051(2) 0.045 Uiso 1 calc R . 
C8A C 0.7283(4) 1.3682(4) 0.7450(3) 0.0565(12) Uani 1 d . . 
H8A1 H 0.7690(5) 1.4397(12) 0.7754(15) 0.085 Uiso 1 calc R . 
H8A2 H 0.6703(15) 1.3329(8) 0.7738(16) 0.085 Uiso 1 calc R . 
H8A3 H 0.6861(19) 1.3960(20) 0.6911(3) 0.085 Uiso 1 calc R . 
C9A C 1.0817(5) 1.1588(5) 1.0677(3) 0.0692(14) Uani 1 d . . 
H9A1 H 1.1649(10) 1.1880(28) 1.0761(6) 0.104 Uiso 1 calc R . 
H9A2 H 1.0810(26) 1.0689(6) 1.0787(6) 0.104 Uiso 1 calc R . 
H9A3 H 1.0408(18) 1.2036(25) 1.1044(3) 0.104 Uiso 1 calc R . 
C1'A C 0.8926(3) 1.2327(3) 0.8197(2) 0.0330(8) Uani 1 d . . 
C2'A C 0.8618(4) 1.1329(3) 0.8631(3) 0.0475(10) Uani 1 d . . 
H2'A H 0.7976(4) 1.0795(3) 0.8384(3) 0.057 Uiso 1 calc R . 
C3'A C 0.9231(4) 1.1093(4) 0.9420(3) 0.0572(12) Uani 1 d . . 
H3'A H 0.8995(4) 1.0401(4) 0.9701(3) 0.069 Uiso 1 calc R . 
C4'A C 1.0173(4) 1.1836(4) 0.9808(2) 0.0468(10) Uani 1 d . . 
C5'A C 1.0494(4) 1.2807(4) 0.9365(3) 0.0478(10) Uani 1 d . . 
H5'A H 1.1156(4) 1.3319(4) 0.9605(3) 0.057 Uiso 1 calc R . 
C6'A C 0.9891(3) 1.3060(4) 0.8588(2) 0.0422(9) Uani 1 d . . 
H6'A H 1.0135(3) 1.3750(4) 0.8310(2) 0.051 Uiso 1 calc R . 
O1B O 1.1504(2) 1.3075(3) 0.7289(2) 0.0459(7) Uani 1 d . . 
O2B O 1.2754(2) 1.4132(2) 0.6763(2) 0.0471(7) Uani 1 d . . 
N1B N 1.4961(3) 1.1183(3) 0.6812(2) 0.0372(8) Uani 1 d . . 
N2B N 1.5453(3) 0.9150(3) 0.7105(2) 0.0353(7) Uani 1 d . . 
H2B H 1.6066(3) 0.9304(3) 0.6882(2) 0.042 Uiso 1 calc R . 
N5B N 1.2423(3) 1.3149(3) 0.7029(2) 0.0368(7) Uani 1 d . . 
C2B C 1.4663(3) 1.0087(3) 0.7113(2) 0.0294(8) Uani 1 d . . 
C3B C 1.3609(3) 0.9945(3) 0.7404(2) 0.0306(8) Uani 1 d . . 
H3B H 1.3426(3) 0.9171(3) 0.7624(2) 0.037 Uiso 1 calc R . 
C4B C 1.2857(3) 1.0935(3) 0.7365(2) 0.0312(8) Uani 1 d . . 
H4B H 1.2133(3) 1.0867(3) 0.7553(2) 0.037 Uiso 1 calc R . 
C5B C 1.3169(3) 1.2055(3) 0.7045(2) 0.0294(8) Uani 1 d . . 
C6B C 1.4211(3) 1.2137(3) 0.6779(2) 0.0353(9) Uani 1 d . . 
H6B H 1.4407(3) 1.2908(3) 0.6561(2) 0.042 Uiso 1 calc R . 
C7B C 1.5371(3) 0.7907(3) 0.7434(2) 0.0373(9) Uani 1 d . . 
H7B H 1.4552(3) 0.7563(3) 0.7208(2) 0.045 Uiso 1 calc R . 
C8B C 1.6298(4) 0.7098(4) 0.7143(3) 0.0612(13) Uani 1 d . . 
H8B1 H 1.6293(20) 0.6254(9) 0.7367(16) 0.092 Uiso 1 calc R . 
H8B2 H 1.7098(6) 0.7466(16) 0.7324(16) 0.092 Uiso 1 calc R . 
H8B3 H 1.6097(16) 0.7055(24) 0.6551(3) 0.092 Uiso 1 calc R . 
C9B C 1.6199(7) 0.7784(11) 1.0968(4) 0.168(4) Uani 1 d . . 
H9B1 H 1.5547(37) 0.8228(61) 1.1141(5) 0.251 Uiso 1 calc R . 
H9B2 H 1.6967(33) 0.8181(61) 1.1211(4) 0.251 Uiso 1 calc R . 
H9B3 H 1.6211(65) 0.6910(12) 1.1143(5) 0.251 Uiso 1 calc R . 
C1'B C 1.5590(3) 0.7908(3) 0.8351(2) 0.0344(9) Uani 1 d . . 
C2'B C 1.6045(3) 0.8931(4) 0.8814(2) 0.0446(10) Uani 1 d . . 
H2'B H 1.6217(3) 0.9677(4) 0.8558(2) 0.054 Uiso 1 calc R . 
C3'B C 1.6251(4) 0.8874(6) 0.9655(3) 0.0705(15) Uani 1 d . . 
H3'B H 1.6578(4) 0.9584(6) 0.9963(3) 0.085 Uiso 1 calc R . 
C4'B C 1.5998(5) 0.7836(8) 1.0047(3) 0.085(2) Uani 1 d . . 
C5'B C 1.5549(5) 0.6809(6) 0.9581(4) 0.083(2) Uani 1 d . . 
H5'B H 1.5374(5) 0.6067(6) 0.9841(4) 0.099 Uiso 1 calc R . 
C6'B C 1.5350(4) 0.6840(4) 0.8745(3) 0.0588(12) Uani 1 d . . 
H6'B H 1.5044(4) 0.6121(4) 0.8440(3) 0.071 Uiso 1 calc R . 
O1C O 1.5053(2) 1.4206(3) 0.5463(2) 0.0506(7) Uani 1 d . . 
O2C O 1.6210(3) 1.5721(3) 0.5259(2) 0.0554(8) Uani 1 d . . 
N1C N 1.8167(3) 1.3479(2) 0.4123(2) 0.0321(7) Uani 1 d . . 
N2C N 1.8574(2) 1.1524(3) 0.3688(2) 0.0327(7) Uani 1 d . . 
H2C H 1.8466(2) 1.0710(3) 0.3696(2) 0.039 Uiso 1 calc R . 
N5C N 1.5907(3) 1.4611(3) 0.5202(2) 0.0374(8) Uani 1 d . . 
C2C C 1.7884(3) 1.2249(3) 0.4051(2) 0.0263(8) Uani 1 d . . 
C3C C 1.6929(3) 1.1738(3) 0.4354(2) 0.0309(8) Uani 1 d . . 
H3C H 1.6747(3) 1.0872(3) 0.4293(2) 0.037 Uiso 1 calc R . 
C4C C 1.6272(3) 1.2495(3) 0.4735(2) 0.0319(8) Uani 1 d . . 
H4C H 1.5622(3) 1.2173(3) 0.4939(2) 0.038 Uiso 1 calc R . 
C5C C 1.6576(3) 1.3751(3) 0.4816(2) 0.0289(8) Uani 1 d . . 
C6C C 1.7513(3) 1.4199(3) 0.4505(2) 0.0326(8) Uani 1 d . . 
H6C H 1.7703(3) 1.5064(3) 0.4566(2) 0.039 Uiso 1 calc R . 
C7C C 1.9483(3) 1.1988(3) 0.3283(2) 0.0332(8) Uani 1 d . . 
H7C H 1.9895(3) 1.2708(3) 0.3606(2) 0.040 Uiso 1 calc R . 
C8C C 2.0422(3) 1.0979(4) 0.3274(3) 0.0435(10) Uani 1 d . . 
H8C1 H 2.1006(13) 1.1280(9) 0.2971(13) 0.065 Uiso 1 calc R . 
H8C2 H 2.0029(4) 1.0224(9) 0.3015(13) 0.065 Uiso 1 calc R . 
H8C3 H 2.0836(15) 1.0785(17) 0.3831(3) 0.065 Uiso 1 calc R . 
C9C C 1.7433(5) 1.3778(5) 0.0017(3) 0.0748(15) Uani 1 d . . 
H9C1 H 1.7859(21) 1.3392(26) -0.0365(4) 0.112 Uiso 1 calc R . 
H9C2 H 1.7510(28) 1.4689(6) -0.0006(6) 0.112 Uiso 1 calc R . 
H9C3 H 1.6583(9) 1.3547(28) -0.0130(8) 0.112 Uiso 1 calc R . 
C1'C C 1.8942(3) 1.2464(3) 0.2435(2) 0.0339(9) Uani 1 d . . 
C2'C C 1.9248(3) 1.3615(3) 0.2181(2) 0.0399(9) Uani 1 d . . 
H2'C H 1.9799(3) 1.4128(3) 0.2543(2) 0.048 Uiso 1 calc R . 
C3'C C 1.8761(4) 1.4040(4) 0.1400(3) 0.0503(11) Uani 1 d . . 
H3'C H 1.8984(4) 1.4841(4) 0.1240(3) 0.060 Uiso 1 calc R . 
C4'C C 1.7969(4) 1.3328(4) 0.0861(3) 0.0491(11) Uani 1 d . . 
C5'C C 1.7670(4) 1.2168(5) 0.1114(3) 0.0562(11) Uani 1 d . . 
H5'C H 1.7134(4) 1.1648(5) 0.0747(3) 0.067 Uiso 1 calc R . 
C6'C C 1.8138(4) 1.1746(4) 0.1895(2) 0.0483(10) Uani 1 d . . 
H6'C H 1.7902(4) 1.0954(4) 0.2059(2) 0.058 Uiso 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 
O1A 0.042(2) 0.050(2) 0.037(2) -0.0046(11) 0.0156(13) 0.0009(12) 
O2A 0.054(2) 0.0289(15) 0.050(2) -0.0079(11) 0.0135(14) -0.0016(13) 
N1A 0.032(2) 0.031(2) 0.036(2) -0.0019(13) 0.0109(14) -0.0003(13) 
N2A 0.035(2) 0.039(2) 0.041(2) -0.0119(14) 0.0104(15) 0.0007(14) 
N5A 0.033(2) 0.032(2) 0.032(2) -0.0010(13) 0.0062(15) 0.0054(14) 
C2A 0.028(2) 0.027(2) 0.029(2) 0.0005(15) 0.003(2) 0.0060(15) 
C3A 0.028(2) 0.022(2) 0.037(2) 0.0011(15) 0.002(2) 0.0022(14) 
C4A 0.025(2) 0.031(2) 0.035(2) 0.007(2) 0.007(2) 0.003(2) 
C5A 0.034(2) 0.022(2) 0.028(2) 0.0015(14) 0.005(2) 0.0054(15) 
C6A 0.029(2) 0.025(2) 0.031(2) -0.0003(15) 0.003(2) 0.0022(14) 
C7A 0.046(2) 0.028(2) 0.039(2) -0.005(2) 0.011(2) 0.000(2) 
C8A 0.067(3) 0.043(2) 0.051(3) -0.010(2) -0.006(2) 0.020(2) 
C9A 0.069(3) 0.085(3) 0.051(3) 0.002(2) 0.006(3) 0.030(3) 
C1'A 0.034(2) 0.028(2) 0.040(2) -0.007(2) 0.015(2) 0.003(2) 
C2'A 0.046(2) 0.042(2) 0.052(3) 0.004(2) 0.004(2) -0.008(2) 
C3'A 0.060(3) 0.050(3) 0.059(3) 0.019(2) 0.007(3) 0.001(2) 
C4'A 0.042(2) 0.053(3) 0.045(3) -0.004(2) 0.009(2) 0.016(2) 
C5'A 0.038(2) 0.052(3) 0.055(3) -0.015(2) 0.013(2) -0.005(2) 
C6'A 0.044(2) 0.043(2) 0.042(3) -0.009(2) 0.014(2) -0.008(2) 
O1B 0.040(2) 0.054(2) 0.048(2) 0.0055(13) 0.0173(14) 0.0148(13) 
O2B 0.047(2) 0.0295(14) 0.065(2) 0.0104(13) 0.0130(15) 0.0079(12) 
N1B 0.040(2) 0.034(2) 0.042(2) 0.0127(14) 0.018(2) 0.0108(15) 
N2B 0.040(2) 0.033(2) 0.037(2) 0.0079(13) 0.0162(15) 0.0125(14) 
N5B 0.034(2) 0.041(2) 0.035(2) 0.0030(14) 0.008(2) 0.0112(15) 
C2B 0.033(2) 0.034(2) 0.021(2) 0.0028(15) 0.005(2) 0.008(2) 
C3B 0.038(2) 0.028(2) 0.027(2) 0.0024(14) 0.008(2) -0.001(2) 
C4B 0.028(2) 0.038(2) 0.028(2) -0.001(2) 0.008(2) 0.000(2) 
C5B 0.029(2) 0.028(2) 0.029(2) 0.0005(14) 0.003(2) 0.0063(15) 
C6B 0.037(2) 0.032(2) 0.041(2) 0.009(2) 0.017(2) 0.008(2) 
C7B 0.039(2) 0.031(2) 0.040(2) 0.000(2) 0.005(2) 0.004(2) 
C8B 0.090(4) 0.038(2) 0.060(3) -0.004(2) 0.025(3) 0.022(2) 
C9B 0.104(5) 0.354(13) 0.044(4) 0.073(6) 0.015(4) 0.064(7) 
C1'B 0.032(2) 0.033(2) 0.039(2) 0.011(2) 0.007(2) 0.007(2) 
C2'B 0.042(2) 0.053(3) 0.038(2) 0.002(2) 0.006(2) 0.005(2) 
C3'B 0.053(3) 0.108(4) 0.045(3) -0.013(3) -0.001(2) 0.011(3) 
C4'B 0.047(3) 0.162(6) 0.045(3) 0.037(4) 0.007(3) 0.025(4) 
C5'B 0.058(3) 0.111(5) 0.082(4) 0.066(4) 0.020(3) 0.012(3) 
C6'B 0.049(3) 0.059(3) 0.069(3) 0.025(2) 0.014(2) -0.001(2) 
O1C 0.040(2) 0.062(2) 0.057(2) 0.0071(14) 0.026(2) 0.0072(14) 
O2C 0.058(2) 0.041(2) 0.074(2) -0.0156(14) 0.028(2) -0.0003(14) 
N1C 0.033(2) 0.030(2) 0.035(2) -0.0033(13) 0.0127(14) -0.0049(13) 
N2C 0.039(2) 0.0271(15) 0.036(2) -0.0043(12) 0.0156(15) -0.0040(13) 
N5C 0.034(2) 0.048(2) 0.032(2) 0.0005(14) 0.010(2) 0.005(2) 
C2C 0.027(2) 0.029(2) 0.022(2) -0.0005(14) 0.003(2) -0.001(2) 
C3C 0.030(2) 0.031(2) 0.031(2) 0.0058(15) 0.004(2) -0.001(2) 
C4C 0.030(2) 0.037(2) 0.030(2) 0.0085(15) 0.009(2) 0.001(2) 
C5C 0.028(2) 0.033(2) 0.027(2) -0.0008(14) 0.007(2) 0.004(2) 
C6C 0.037(2) 0.030(2) 0.031(2) -0.002(2) 0.005(2) 0.000(2) 
C7C 0.033(2) 0.032(2) 0.035(2) -0.0063(15) 0.010(2) -0.006(2) 
C8C 0.038(2) 0.047(2) 0.048(3) -0.003(2) 0.014(2) 0.005(2) 
C9C 0.070(3) 0.096(4) 0.060(3) 0.024(3) 0.016(3) 0.021(3) 
C1'C 0.033(2) 0.036(2) 0.036(2) -0.005(2) 0.015(2) -0.002(2) 
C2'C 0.047(2) 0.031(2) 0.046(3) -0.006(2) 0.020(2) -0.004(2) 
C3'C 0.066(3) 0.037(2) 0.056(3) 0.009(2) 0.032(3) 0.010(2) 
C4'C 0.046(3) 0.065(3) 0.041(3) 0.006(2) 0.019(2) 0.011(2) 
C5'C 0.048(3) 0.079(3) 0.040(3) -0.003(2) 0.006(2) -0.016(2) 
C6'C 0.053(3) 0.046(2) 0.044(3) 0.000(2) 0.007(2) -0.018(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 
O1A N5A 1.228(4) . ? 
O2A N5A 1.239(4) . ? 
N1A C6A 1.324(4) . ? 
N1A C2A 1.365(4) . ? 
N2A C2A 1.344(4) . ? 
N2A C7A 1.457(4) . ? 
N5A C5A 1.442(4) . ? 
C2A C3A 1.410(5) . ? 
C3A C4A 1.360(5) . ? 
C4A C5A 1.390(5) . ? 
C5A C6A 1.379(5) . ? 
C7A C8A 1.517(5) . ? 
C7A C1'A 1.518(5) . ? 
C9A C4'A 1.517(6) . ? 
C1'A C2'A 1.384(5) . ? 
C1'A C6'A 1.395(5) . ? 
C2'A C3'A 1.389(6) . ? 
C3'A C4'A 1.383(6) . ? 
C4'A C5'A 1.378(6) . ? 
C5'A C6'A 1.371(6) . ? 
O1B N5B 1.225(4) . ? 
O2B N5B 1.234(4) . ? 
N1B C6B 1.325(4) . ? 
N1B C2B 1.352(4) . ? 
N2B C2B 1.351(4) . ? 
N2B C7B 1.452(5) . ? 
N5B C5B 1.445(4) . ? 
C2B C3B 1.404(5) . ? 
C3B C4B 1.356(5) . ? 
C4B C5B 1.393(5) . ? 
C5B C6B 1.364(5) . ? 
C7B C1'B 1.518(5) . ? 
C7B C8B 1.530(5) . ? 
C9B C4'B 1.527(8) . ? 
C1'B C2'B 1.379(5) . ? 
C1'B C6'B 1.380(5) . ? 
C2'B C3'B 1.393(6) . ? 
C3'B C4'B 1.357(8) . ? 
C4'B C5'B 1.384(9) . ? 
C5'B C6'B 1.384(7) . ? 
O1C N5C 1.233(4) . ? 
O2C N5C 1.235(4) . ? 
N1C C6C 1.335(4) . ? 
N1C C2C 1.353(4) . ? 
N2C C2C 1.346(4) . ? 
N2C C7C 1.450(4) . ? 
N5C C5C 1.441(4) . ? 
C2C C3C 1.414(4) . ? 
C3C C4C 1.358(5) . ? 
C4C C5C 1.386(5) . ? 
C5C C6C 1.378(5) . ? 
C7C C1'C 1.521(5) . ? 
C7C C8C 1.523(5) . ? 
C9C C4'C 1.506(6) . ? 
C1'C C2'C 1.374(5) . ? 
C1'C C6'C 1.379(5) . ? 
C2'C C3'C 1.394(6) . ? 
C3'C C4'C 1.368(6) . ? 
C4'C C5'C 1.380(6) . ? 
C5'C C6'C 1.389(6) . ? 
 
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 
C6A N1A C2A 118.1(3) . . ? 
C2A N2A C7A 126.3(3) . . ? 
O1A N5A O2A 122.8(3) . . ? 
O1A N5A C5A 118.6(3) . . ? 
O2A N5A C5A 118.7(3) . . ? 
N2A C2A N1A 114.9(3) . . ? 
N2A C2A C3A 123.5(3) . . ? 
N1A C2A C3A 121.5(3) . . ? 
C4A C3A C2A 119.2(3) . . ? 
C3A C4A C5A 118.4(3) . . ? 
C6A C5A C4A 120.1(3) . . ? 
C6A C5A N5A 119.7(3) . . ? 
C4A C5A N5A 120.2(3) . . ? 
N1A C6A C5A 122.5(3) . . ? 
N2A C7A C8A 108.7(3) . . ? 
N2A C7A C1'A 112.9(3) . . ? 
C8A C7A C1'A 110.0(3) . . ? 
C2'A C1'A C6'A 116.6(4) . . ? 
C2'A C1'A C7A 122.8(3) . . ? 
C6'A C1'A C7A 120.4(3) . . ? 
C1'A C2'A C3'A 121.1(4) . . ? 
C4'A C3'A C2'A 122.0(4) . . ? 
C5'A C4'A C3'A 116.5(4) . . ? 
C5'A C4'A C9A 122.0(4) . . ? 
C3'A C4'A C9A 121.5(4) . . ? 
C6'A C5'A C4'A 122.3(4) . . ? 
C5'A C6'A C1'A 121.5(4) . . ? 
C6B N1B C2B 118.1(3) . . ? 
C2B N2B C7B 125.2(3) . . ? 
O1B N5B O2B 122.7(3) . . ? 
O1B N5B C5B 119.2(3) . . ? 
O2B N5B C5B 118.1(3) . . ? 
N2B C2B N1B 114.6(3) . . ? 
N2B C2B C3B 123.3(3) . . ? 
N1B C2B C3B 122.1(3) . . ? 
C4B C3B C2B 118.7(3) . . ? 
C3B C4B C5B 118.5(3) . . ? 
C6B C5B C4B 120.0(3) . . ? 
C6B C5B N5B 119.7(3) . . ? 
C4B C5B N5B 120.2(3) . . ? 
N1B C6B C5B 122.6(3) . . ? 
N2B C7B C1'B 112.5(3) . . ? 
N2B C7B C8B 106.7(3) . . ? 
C1'B C7B C8B 111.1(3) . . ? 
C2'B C1'B C6'B 118.2(4) . . ? 
C2'B C1'B C7B 122.6(3) . . ? 
C6'B C1'B C7B 119.2(4) . . ? 
C1'B C2'B C3'B 120.3(4) . . ? 
C4'B C3'B C2'B 121.9(5) . . ? 
C3'B C4'B C5'B 117.6(5) . . ? 
C3'B C4'B C9B 121.9(8) . . ? 
C5'B C4'B C9B 120.5(7) . . ? 
C4'B C5'B C6'B 121.4(5) . . ? 
C1'B C6'B C5'B 120.6(5) . . ? 
C6C N1C C2C 117.2(3) . . ? 
C2C N2C C7C 124.7(3) . . ? 
O1C N5C O2C 122.7(3) . . ? 
O1C N5C C5C 118.5(3) . . ? 
O2C N5C C5C 118.8(3) . . ? 
N2C C2C N1C 116.7(3) . . ? 
N2C C2C C3C 121.2(3) . . ? 
N1C C2C C3C 122.1(3) . . ? 
C4C C3C C2C 119.4(3) . . ? 
C3C C4C C5C 118.2(3) . . ? 
C6C C5C C4C 119.8(3) . . ? 
C6C C5C N5C 118.9(3) . . ? 
C4C C5C N5C 121.2(3) . . ? 
N1C C6C C5C 123.2(3) . . ? 
N2C C7C C1'C 112.1(3) . . ? 
N2C C7C C8C 109.9(3) . . ? 
C1'C C7C C8C 111.7(3) . . ? 
C2'C C1'C C6'C 118.0(4) . . ? 
C2'C C1'C C7C 121.1(3) . . ? 
C6'C C1'C C7C 120.9(3) . . ? 
C1'C C2'C C3'C 120.9(4) . . ? 
C4'C C3'C C2'C 121.3(4) . . ? 
C3'C C4'C C5'C 117.8(4) . . ? 
C3'C C4'C C9C 121.9(4) . . ? 
C5'C C4'C C9C 120.4(4) . . ? 
C4'C C5'C C6'C 121.2(4) . . ? 
C1'C C6'C C5'C 120.8(4) . . ? 
 
_refine_diff_density_max    0.296 
_refine_diff_density_min   -0.265 
_refine_diff_density_rms    0.066 

#===END
 

data_compound_6
 
_audit_creation_method            SHELXL
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C14 H15 N3 O2'
_chemical_formula_weight          257.29
_chemical_melting_point           371-373
_chemical_compound_source         ?
 
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    P21
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    8.9790(10)
_cell_length_b                    15.977(2)
_cell_length_c                    9.410(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  96.520(10)
_cell_angle_gamma                 90.00
_cell_volume                      1341.2(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     250
_cell_measurement_theta_min       2.18
_cell_measurement_theta_max       24.88
 
_exptl_crystal_description        block
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.42
_exptl_crystal_size_mid           0.28
_exptl_crystal_size_min           0.28
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.274
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              544
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
 
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71069  
_diffrn_radiation_type            MoK\a  
_diffrn_radiation_source          'rotating anode source' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        'Delft Instruments FAST-TV area-
detector'
_diffrn_measurement_method        'Darr et al. (1993)'
_diffrn_standards_number          'not measured'
_diffrn_standards_interval_count  'not measured'
_diffrn_standards_interval_time    'not measured'
_diffrn_standards_decay_%          'not measured' 
_diffrn_reflns_number             5980
_diffrn_reflns_av_R_equivalents   0.1075
_diffrn_reflns_av_sigmaI/netI     0.0907
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          2.18
_diffrn_reflns_theta_max          24.88
_reflns_number_total              3752
_reflns_number_observed           2870
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection       'MADNES (Pflugrath & 
Messerschmidt,1989)' 
_computing_cell_refinement        'REFINE (incorporated in MADNES)' 
_computing_data_reduction         'ABSMAD (Karaulov, 1991)'
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     ?
_computing_publication_material   'SHELXL-93 (Sheldrick, 1993)'  
 
_refine_special_details
;
 Refinement on F^2^ for ALL reflections except for 65 with very negative
F^2^
 or flagged by the user for potential systematic errors.  Weighted R-
factors
 wR and all goodnesses 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 observed
criterion
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0579P)^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     riding
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    1.54(152)
_refine_ls_number_reflns          3687
_refine_ls_number_parameters      346
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0643
_refine_ls_R_factor_obs           0.0481
_refine_ls_wR_factor_all          0.1351
_refine_ls_wR_factor_obs          0.1101
_refine_ls_goodness_of_fit_all    0.942
_refine_ls_goodness_of_fit_obs    1.029
_refine_ls_restrained_S_all       1.089
_refine_ls_restrained_S_obs       1.029
_refine_ls_shift/esd_max          -0.004
_refine_ls_shift/esd_mean         0.001
 
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_thermal_displace_type
 _atom_site_occupancy
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_group
O1A O 0.6841(3) -0.0146(2) 0.2447(3) 0.0982(9) Uani 1 d . .
O2A O 0.6767(3) -0.1322(2) 0.3582(3) 0.0875(8) Uani 1 d . .
N1A N 0.4435(3) -0.0303(2) 0.6591(3) 0.0596(7) Uani 1 d . .
N2A N 0.3333(3) 0.08453(14) 0.7540(3) 0.0560(7) Uani 1 d . .
N5A N 0.6459(3) -0.0580(2) 0.3426(3) 0.0676(8) Uani 1 d . .
C2A C 0.4061(3) 0.0510(2) 0.6481(3) 0.0499(8) Uani 1 d . .
C3A C 0.4408(4) 0.0999(2) 0.5323(4) 0.0591(9) Uani 1 d . .
H3A H 0.4116(4) 0.1557(2) 0.5252(4) 0.071 Uiso 1 calc R .
C4A C 0.5183(4) 0.0647(2) 0.4295(3) 0.0619(9) Uani 1 d . .
H4A H 0.5430(4) 0.0961(2) 0.3523(3) 0.074 Uiso 1 calc R .
C5A C 0.5582(3) -0.0181(2) 0.4441(3) 0.0547(8) Uani 1 d . .
C6A C 0.5182(4) -0.0637(2) 0.5569(3) 0.0624(9) Uani 1 d . .
H6A H 0.5439(4) -0.1201(2) 0.5632(3) 0.075 Uiso 1 calc R .
C7A C 0.2983(4) 0.0351(2) 0.8784(3) 0.0575(8) Uani 1 d . .
H7A H 0.3299(4) -0.0225(2) 0.8623(3) 0.069 Uiso 1 calc R .
C8A C 0.3891(5) 0.0649(3) 1.0161(4) 0.0863(11) Uani 1 d . .
H8A1 H 0.4938(5) 0.0646(3) 1.0039(4) 0.130 Uiso 1 calc R .
H8A2 H 0.3716(5) 0.0282(3) 1.0932(4) 0.130 Uiso 1 calc R .
H8A3 H 0.3590(5) 0.1207(3) 1.0377(4) 0.130 Uiso 1 calc R .
C9A C 0.2884(4) 0.1716(2) 0.7489(4) 0.0748(10) Uani 1 d . .
H9A1 H 0.2388(4) 0.1845(2) 0.8313(4) 0.112 Uiso 1 calc R .
H9A2 H 0.2211(4) 0.1815(2) 0.6637(4) 0.112 Uiso 1 calc R .
H9A3 H 0.3754(4) 0.2064(2) 0.7481(4) 0.112 Uiso 1 calc R .
C1'A C 0.1294(4) 0.0328(2) 0.8839(3) 0.0567(8) Uani 1 d . .
C2'A C 0.0409(5) -0.0129(3) 0.7810(4) 0.0766(10) Uani 1 d . .
H2'A H 0.0869(5) -0.0411(3) 0.7113(4) 0.092 Uiso 1 calc R .
C3'A C -0.1092(5) -0.0179(3) 0.7785(5) 0.0971(13) Uani 1 d . .
H3'A H -0.1649(5) -0.0495(3) 0.7083(5) 0.117 Uiso 1 calc R .
C4'A C -0.1792(5) 0.0233(3) 0.8790(6) 0.1005(14) Uani 1 d . .
H4'A H -0.2829(5) 0.0203(3) 0.8766(6) 0.121 Uiso 1 calc R .
C5'A C -0.0991(6) 0.0682(3) 0.9815(6) 0.1022(15) Uani 1 d . .
H5'A H -0.1476(6) 0.0958(3) 1.0501(6) 0.123 Uiso 1 calc R .
C6'A C 0.0571(5) 0.0738(3) 0.9856(4) 0.0812(11) Uani 1 d . .
H6'A H 0.1120(5) 0.1050(3) 1.0568(4) 0.097 Uiso 1 calc R .
O1B O 0.2955(3) 0.2937(2) 0.1260(3) 0.1026(10) Uani 1 d . .
O2B O 0.4551(3) 0.2504(2) 0.2975(3) 0.0811(8) Uani 1 d . .
N1B N 0.6190(3) 0.3413(2) -0.1293(2) 0.0574(7) Uani 1 d . .
N2B N 0.8678(3) 0.3355(2) -0.1713(3) 0.0582(7) Uani 1 d . .
N5B N 0.4247(3) 0.2797(2) 0.1777(3) 0.0626(7) Uani 1 d . .
C2B C 0.7631(3) 0.3245(2) -0.0797(3) 0.0486(7) Uani 1 d . .
C3B C 0.8036(4) 0.2969(2) 0.0626(3) 0.0600(8) Uani 1 d . .
H3B H 0.9037(4) 0.2887(2) 0.0972(3) 0.072 Uiso 1 calc R .
C4B C 0.6933(4) 0.2827(2) 0.1480(3) 0.0599(8) Uani 1 d . .
H4B H 0.7169(4) 0.2637(2) 0.2413(3) 0.072 Uiso 1 calc R .
C5B C 0.5459(4) 0.2968(2) 0.0936(3) 0.0523(7) Uani 1 d . .
C6B C 0.5142(4) 0.3275(2) -0.0429(3) 0.0555(8) Uani 1 d . .
H6B H 0.4149(4) 0.3391(2) -0.0765(3) 0.067 Uiso 1 calc R .
C7B C 0.8261(4) 0.3594(2) -0.3223(3) 0.0586(8) Uani 1 d . .
H7B H 0.7166(4) 0.3559(2) -0.3409(3) 0.070 Uiso 1 calc R .
C8B C 0.8691(5) 0.4497(2) -0.3459(4) 0.0799(11) Uani 1 d . .
H8B1 H 0.8239(5) 0.4851(2) -0.2805(4) 0.120 Uiso 1 calc R .
H8B2 H 0.8345(5) 0.4658(2) -0.4424(4) 0.120 Uiso 1 calc R .
H8B3 H 0.9761(5) 0.4553(2) -0.3300(4) 0.120 Uiso 1 calc R .
C9B C 1.0261(4) 0.3276(2) -0.1206(3) 0.0700(10) Uani 1 d . .
H9B1 H 1.0844(4) 0.3372(2) -0.1985(3) 0.105 Uiso 1 calc R .
H9B2 H 1.0458(4) 0.2723(2) -0.0833(3) 0.105 Uiso 1 calc R .
H9B3 H 1.0527(4) 0.3680(2) -0.0467(3) 0.105 Uiso 1 calc R .
C1'B C 0.8903(3) 0.2961(2) -0.4193(3) 0.0551(8) Uani 1 d . .
C2'B C 0.9969(4) 0.3158(2) -0.5078(3) 0.0607(8) Uani 1 d . .
H2'B H 1.0328(4) 0.3703(2) -0.5093(3) 0.073 Uiso 1 calc R .
C3'B C 1.0523(4) 0.2555(3) -0.5955(4) 0.0755(11) Uani 1 d . .
H3'B H 1.1246(4) 0.2699(3) -0.6546(4) 0.091 Uiso 1 calc R .
C4'B C 1.0000(6) 0.1758(3) -0.5942(5) 0.0883(13) Uani 1 d . .
H4'B H 1.0367(6) 0.1355(3) -0.6526(5) 0.106 Uiso 1 calc R .
C5'B C 0.8944(6) 0.1544(3) -0.5081(5) 0.0962(13) Uani 1 d . .
H5'B H 0.8587(6) 0.0998(3) -0.5084(5) 0.115 Uiso 1 calc R .
C6'B C 0.8401(5) 0.2135(3) -0.4203(4) 0.0805(11) Uani 1 d . .
H6'B H 0.7688(5) 0.1980(3) -0.3609(4) 0.097 Uiso 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
O1A 0.102(2) 0.123(2) 0.076(2) 0.001(2) 0.039(2) 0.006(2)
O2A 0.092(2) 0.093(2) 0.077(2) -0.0140(15) 0.0099(14) 0.034(2)
N1A 0.077(2) 0.051(2) 0.053(2) 0.0034(12) 0.0166(13) 0.0077(13)
N2A 0.068(2) 0.0452(15) 0.057(2) 0.0039(12) 0.0175(14) 0.0038(12)
N5A 0.062(2) 0.087(2) 0.054(2) -0.009(2) 0.0067(15) 0.007(2)
C2A 0.051(2) 0.049(2) 0.050(2) 0.0002(14) 0.0064(14) -0.0013(14)
C3A 0.066(2) 0.052(2) 0.061(2) 0.006(2) 0.013(2) 0.000(2)
C4A 0.066(2) 0.069(2) 0.051(2) 0.008(2) 0.011(2) -0.002(2)
C5A 0.053(2) 0.065(2) 0.046(2) -0.006(2) 0.0076(14) 0.003(2)
C6A 0.072(2) 0.058(2) 0.058(2) -0.002(2) 0.010(2) 0.011(2)
C7A 0.070(2) 0.056(2) 0.048(2) 0.0013(14) 0.013(2) 0.005(2)
C8A 0.083(3) 0.110(3) 0.064(2) -0.002(2) 0.002(2) 0.000(2)
C9A 0.088(3) 0.059(2) 0.080(2) -0.004(2) 0.020(2) 0.007(2)
C1'A 0.071(2) 0.053(2) 0.048(2) 0.0017(14) 0.016(2) 0.005(2)
C2'A 0.072(3) 0.095(3) 0.065(2) -0.011(2) 0.016(2) -0.002(2)
C3'A 0.083(4) 0.120(4) 0.089(3) -0.010(3) 0.016(3) -0.013(3)
C4'A 0.063(3) 0.117(4) 0.124(4) 0.016(3) 0.019(3) -0.006(3)
C5'A 0.091(4) 0.110(3) 0.116(4) -0.010(3) 0.057(3) 0.010(3)
C6'A 0.092(3) 0.080(2) 0.077(3) -0.011(2) 0.030(2) 0.002(2)
O1B 0.063(2) 0.157(3) 0.093(2) 0.032(2) 0.028(2) 0.011(2)
O2B 0.109(2) 0.077(2) 0.063(2) 0.0188(13) 0.0355(14) 0.0021(13)
N1B 0.049(2) 0.075(2) 0.0487(15) 0.0069(13) 0.0084(13) 0.0025(13)
N2B 0.0412(15) 0.085(2) 0.049(2) 0.0057(13) 0.0076(12) 0.0065(13)
N5B 0.074(2) 0.063(2) 0.055(2) 0.0039(14) 0.025(2) 0.002(2)
C2B 0.045(2) 0.054(2) 0.047(2) -0.0019(13) 0.0068(14) 0.0025(14)
C3B 0.057(2) 0.078(2) 0.044(2) 0.005(2) 0.0038(14) 0.010(2)
C4B 0.077(2) 0.063(2) 0.041(2) 0.0038(15) 0.010(2) 0.009(2)
C5B 0.058(2) 0.053(2) 0.048(2) -0.0002(14) 0.0154(14) -0.0016(14)
C6B 0.049(2) 0.068(2) 0.051(2) 0.003(2) 0.0076(15) 0.0025(15)
C7B 0.056(2) 0.075(2) 0.046(2) 0.008(2) 0.0111(14) 0.005(2)
C8B 0.096(3) 0.072(2) 0.073(3) 0.010(2) 0.019(2) 0.021(2)
C9B 0.051(2) 0.100(3) 0.060(2) 0.003(2) 0.011(2) 0.009(2)
C1'B 0.049(2) 0.069(2) 0.046(2) 0.004(2) 0.0029(14) 0.000(2)
C2'B 0.060(2) 0.072(2) 0.051(2) 0.008(2) 0.014(2) 0.002(2)
C3'B 0.075(3) 0.104(3) 0.051(2) 0.002(2) 0.017(2) 0.015(2)
C4'B 0.103(3) 0.087(3) 0.072(3) -0.020(2) -0.002(2) 0.021(3)
C5'B 0.115(4) 0.070(3) 0.103(3) -0.011(2) 0.008(3) -0.014(2)
C6'B 0.080(3) 0.085(3) 0.078(3) 0.000(2) 0.015(2) -0.020(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
O1A N5A 1.233(4) . ?
O2A N5A 1.221(4) . ?
N1A C2A 1.342(4) . ?
N1A C6A 1.344(4) . ?
N2A C2A 1.362(4) . ?
N2A C9A 1.448(4) . ?
N2A C7A 1.475(4) . ?
N5A C5A 1.452(4) . ?
C2A C3A 1.405(4) . ?
C3A C4A 1.374(4) . ?
C4A C5A 1.373(5) . ?
C5A C6A 1.369(4) . ?
C7A C1'A 1.524(5) . ?
C7A C8A 1.526(5) . ?
C1'A C6'A 1.381(5) . ?
C1'A C2'A 1.388(5) . ?
C2'A C3'A 1.348(5) . ?
C3'A C4'A 1.364(6) . ?
C4'A C5'A 1.343(7) . ?
C5'A C6'A 1.402(6) . ?
O1B N5B 1.227(4) . ?
O2B N5B 1.223(3) . ?
N1B C6B 1.330(3) . ?
N1B C2B 1.352(4) . ?
N2B C2B 1.357(3) . ?
N2B C9B 1.452(4) . ?
N2B C7B 1.478(4) . ?
N5B C5B 1.442(4) . ?
C2B C3B 1.417(4) . ?
C3B C4B 1.364(4) . ?
C4B C5B 1.383(4) . ?
C5B C6B 1.374(4) . ?
C7B C8B 1.516(5) . ?
C7B C1'B 1.519(4) . ?
C1'B C2'B 1.375(4) . ?
C1'B C6'B 1.394(5) . ?
C2'B C3'B 1.396(5) . ?
C3'B C4'B 1.358(6) . ?
C4'B C5'B 1.358(6) . ?
C5'B C6'B 1.379(6) . ?
 
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
C2A N1A C6A 118.0(3) . . ?
C2A N2A C9A 120.6(3) . . ?
C2A N2A C7A 122.2(2) . . ?
C9A N2A C7A 117.2(3) . . ?
O2A N5A O1A 123.9(3) . . ?
O2A N5A C5A 118.7(3) . . ?
O1A N5A C5A 117.5(3) . . ?
N1A C2A N2A 117.5(2) . . ?
N1A C2A C3A 121.5(3) . . ?
N2A C2A C3A 121.0(3) . . ?
C4A C3A C2A 119.6(3) . . ?
C5A C4A C3A 118.1(3) . . ?
C6A C5A C4A 120.1(3) . . ?
C6A C5A N5A 119.0(3) . . ?
C4A C5A N5A 120.8(3) . . ?
N1A C6A C5A 122.7(3) . . ?
N2A C7A C1'A 110.0(2) . . ?
N2A C7A C8A 111.4(3) . . ?
C1'A C7A C8A 114.6(3) . . ?
C6'A C1'A C2'A 117.1(3) . . ?
C6'A C1'A C7A 124.0(3) . . ?
C2'A C1'A C7A 118.8(3) . . ?
C3'A C2'A C1'A 122.4(4) . . ?
C2'A C3'A C4'A 119.8(4) . . ?
C5'A C4'A C3'A 120.4(4) . . ?
C4'A C5'A C6'A 120.4(4) . . ?
C1'A C6'A C5'A 119.9(4) . . ?
C6B N1B C2B 118.2(2) . . ?
C2B N2B C9B 120.2(2) . . ?
C2B N2B C7B 121.7(2) . . ?
C9B N2B C7B 118.0(2) . . ?
O2B N5B O1B 122.5(3) . . ?
O2B N5B C5B 118.4(3) . . ?
O1B N5B C5B 119.1(3) . . ?
N1B C2B N2B 117.4(2) . . ?
N1B C2B C3B 121.4(2) . . ?
N2B C2B C3B 121.2(3) . . ?
C4B C3B C2B 118.9(3) . . ?
C3B C4B C5B 118.9(3) . . ?
C6B C5B C4B 119.5(3) . . ?
C6B C5B N5B 119.4(3) . . ?
C4B C5B N5B 121.1(3) . . ?
N1B C6B C5B 123.0(3) . . ?
N2B C7B C8B 110.2(3) . . ?
N2B C7B C1'B 109.5(2) . . ?
C8B C7B C1'B 115.1(3) . . ?
C2'B C1'B C6'B 117.3(3) . . ?
C2'B C1'B C7B 123.3(3) . . ?
C6'B C1'B C7B 119.3(3) . . ?
C1'B C2'B C3'B 121.3(3) . . ?
C4'B C3'B C2'B 119.7(4) . . ?
C5'B C4'B C3'B 120.4(4) . . ?
C4'B C5'B C6'B 120.3(4) . . ?
C5'B C6'B C1'B 121.0(4) . . ?
 
_refine_diff_density_max    0.279
_refine_diff_density_min   -0.254
_refine_diff_density_rms    0.075


#===END

data_racemic_compound_2
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H15 N3 O2'
_chemical_formula_weight          257.29
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'O'  'O'   0.0106   0.0060
 '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'
 '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'
 
_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                    6.9781(11)
_cell_length_b                    22.337(4)
_cell_length_c                    8.3899(12)
_cell_angle_alpha                 90.00
_cell_angle_beta                  91.149(12)
_cell_angle_gamma                 90.00
_cell_volume                      1307.5(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     23
_cell_measurement_theta_min       20.86
_cell_measurement_theta_max       23.52
 
_exptl_crystal_description        block
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.75
_exptl_crystal_size_mid           0.40
_exptl_crystal_size_min           0.40
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.307
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              544
_exptl_absorpt_coefficient_mu     0.090
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'AFC7S'
_diffrn_measurement_method        '\w/2\q'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          3
_diffrn_standards_interval_count  150
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         0
_diffrn_reflns_number             3401
_diffrn_reflns_av_R_equivalents   0.0106
_diffrn_reflns_av_sigmaI/netI     0.0370
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        29
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          2.59
_diffrn_reflns_theta_max          28.01
_reflns_number_total              3159
_reflns_number_gt                 2253
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     '?'
_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^)+(0.0298P)^2^+0.4067P] 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      SHELXL
_refine_ls_extinction_coef        0.021(2)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          3159
_refine_ls_number_parameters      233
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0663
_refine_ls_R_factor_gt            0.0398
_refine_ls_wR_factor_ref          0.1188
_refine_ls_wR_factor_gt           0.1006
_refine_ls_goodness_of_fit_ref    1.055
_refine_ls_restrained_S_all       1.055
_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_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.2150(2) 0.38747(6) 0.54607(19) 0.0785(4) Uani 1 d . . .
O2 O 0.0235(2) 0.31657(7) 0.6121(2) 0.0873(5) Uani 1 d . . .
N5 N 0.1702(2) 0.33441(7) 0.54918(18) 0.0582(4) Uani 1 d . . .
N1 N 0.37133(18) 0.18882(6) 0.43412(16) 0.0496(3) Uani 1 d . . .
N2 N 0.63826(19) 0.16384(5) 0.29209(16) 0.0463(3) Uani 1 d . . .
C6 C 0.2584(2) 0.23095(8) 0.4938(2) 0.0521(4) Uani 1 d . . .
C5 C 0.2950(2) 0.29121(7) 0.47721(18) 0.0463(4) Uani 1 d . . .
C4 C 0.4562(2) 0.30993(7) 0.39579(18) 0.0455(3) Uani 1 d . . .
C3 C 0.5762(2) 0.26840(6) 0.33283(17) 0.0413(3) Uani 1 d . . .
C2 C 0.5266(2) 0.20678(6) 0.35409(17) 0.0401(3) Uani 1 d . . .
C31 C 0.7547(3) 0.28558(8) 0.2480(2) 0.0553(4) Uani 1 d . . .
C7 C 0.6195(2) 0.09959(6) 0.32545(18) 0.0436(3) Uani 1 d . . .
C8 C 0.6818(3) 0.06459(9) 0.1793(2) 0.0573(4) Uani 1 d . . .
C1' C 0.7341(2) 0.08249(6) 0.47394(17) 0.0423(3) Uani 1 d . . .
C6' C 0.9297(2) 0.09372(8) 0.4866(2) 0.0547(4) Uani 1 d . . .
C5' C 1.0314(3) 0.07824(10) 0.6234(3) 0.0676(5) Uani 1 d . . .
C4' C 0.9406(3) 0.05099(9) 0.7480(3) 0.0694(5) Uani 1 d . . .
C3' C 0.7486(3) 0.03865(9) 0.7364(2) 0.0640(5) Uani 1 d . . .
C2' C 0.6452(3) 0.05507(7) 0.60078(19) 0.0509(4) Uani 1 d . . .
H6 H 0.145(3) 0.2173(8) 0.550(2) 0.059(5) Uiso 1 d . . .
H4 H 0.486(2) 0.3515(9) 0.383(2) 0.060(5) Uiso 1 d . . .
H311 H 0.776(3) 0.3285(12) 0.246(3) 0.092(7) Uiso 1 d . . .
H312 H 0.754(3) 0.2701(9) 0.136(3) 0.075(6) Uiso 1 d . . .
H313 H 0.870(3) 0.2689(9) 0.301(2) 0.073(6) Uiso 1 d . . .
H2 H 0.743(3) 0.1744(8) 0.247(2) 0.057(5) Uiso 1 d . . .
H7 H 0.484(2) 0.0916(7) 0.3412(19) 0.048(4) Uiso 1 d . . .
H81 H 0.599(3) 0.0752(10) 0.088(3) 0.090(7) Uiso 1 d . . .
H82 H 0.813(3) 0.0754(8) 0.153(2) 0.064(5) Uiso 1 d . . .
H83 H 0.672(3) 0.0197(10) 0.197(2) 0.077(6) Uiso 1 d . . .
H61' H 0.993(3) 0.1118(8) 0.403(2) 0.063(5) Uiso 1 d . . .
H51' H 1.162(3) 0.0884(10) 0.626(3) 0.085(7) Uiso 1 d . . .
H41' H 1.010(3) 0.0400(11) 0.846(3) 0.094(7) Uiso 1 d . . .
H31' H 0.680(3) 0.0197(9) 0.822(2) 0.070(6) Uiso 1 d . . .
H21' H 0.509(3) 0.0473(8) 0.595(2) 0.060(5) Uiso 1 d . . .
 
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 0.0749(9) 0.0529(8) 0.1078(12) -0.0172(7) 0.0070(8) 0.0122(7)
O2 0.0696(9) 0.0782(10) 0.1157(13) -0.0160(9) 0.0430(9) 0.0059(7)
N5 0.0540(8) 0.0569(9) 0.0637(9) -0.0112(7) 0.0027(7) 0.0091(7)
N1 0.0461(7) 0.0423(7) 0.0610(8) 0.0013(6) 0.0120(6) -0.0027(5)
N2 0.0470(7) 0.0366(6) 0.0559(8) 0.0059(6) 0.0135(6) 0.0014(5)
C6 0.0442(8) 0.0510(9) 0.0616(10) -0.0010(7) 0.0125(7) -0.0010(7)
C5 0.0438(8) 0.0439(8) 0.0512(8) -0.0050(6) 0.0024(6) 0.0049(6)
C4 0.0482(8) 0.0398(8) 0.0484(8) 0.0010(6) -0.0019(6) 0.0000(6)
C3 0.0437(7) 0.0372(7) 0.0429(7) 0.0043(6) -0.0001(6) -0.0022(6)
C2 0.0404(7) 0.0386(7) 0.0411(7) 0.0030(6) 0.0005(6) -0.0002(6)
C31 0.0548(10) 0.0467(9) 0.0648(11) 0.0072(8) 0.0141(8) -0.0045(8)
C7 0.0457(8) 0.0350(7) 0.0505(8) 0.0010(6) 0.0084(6) -0.0001(6)
C8 0.0710(12) 0.0488(10) 0.0523(10) -0.0048(7) 0.0068(9) 0.0044(8)
C1' 0.0471(8) 0.0317(7) 0.0484(8) -0.0026(6) 0.0080(6) 0.0015(6)
C6' 0.0475(9) 0.0533(10) 0.0638(10) 0.0015(8) 0.0105(8) 0.0034(7)
C5' 0.0509(10) 0.0690(12) 0.0825(14) -0.0075(10) -0.0054(9) 0.0145(9)
C4' 0.0868(15) 0.0588(11) 0.0621(12) -0.0033(9) -0.0121(11) 0.0196(10)
C3' 0.0881(14) 0.0546(10) 0.0494(10) 0.0024(8) 0.0071(9) -0.0004(10)
C2' 0.0582(10) 0.0429(8) 0.0518(9) -0.0021(7) 0.0097(7) -0.0058(7)
 
_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 N5 1.226(2) . ?
O2 N5 1.228(2) . ?
N5 C5 1.441(2) . ?
N1 C6 1.332(2) . ?
N1 C2 1.3470(18) . ?
N2 C2 1.3469(19) . ?
N2 C7 1.4685(18) . ?
C6 C5 1.378(2) . ?
C5 C4 1.392(2) . ?
C4 C3 1.363(2) . ?
C3 C2 1.431(2) . ?
C3 C31 1.497(2) . ?
C7 C1' 1.515(2) . ?
C7 C8 1.524(2) . ?
C1' C2' 1.385(2) . ?
C1' C6' 1.390(2) . ?
C6' C5' 1.381(3) . ?
C5' C4' 1.375(3) . ?
C4' C3' 1.370(3) . ?
C3' C2' 1.384(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
O1 N5 O2 122.54(15) . . ?
O1 N5 C5 118.82(15) . . ?
O2 N5 C5 118.63(15) . . ?
C2 N1 C6 117.70(13) . . ?
C2 N2 C7 124.61(13) . . ?
N1 C6 C5 122.72(15) . . ?
C6 C5 C4 119.75(14) . . ?
C6 C5 N5 119.83(14) . . ?
C4 C5 N5 120.39(14) . . ?
C3 C4 C5 119.63(14) . . ?
C2 C3 C4 117.01(13) . . ?
C4 C3 C31 122.22(14) . . ?
C2 C3 C31 120.76(14) . . ?
N1 C2 N2 117.25(13) . . ?
N2 C2 C3 119.56(13) . . ?
N1 C2 C3 123.19(13) . . ?
N2 C7 C1' 110.82(12) . . ?
N2 C7 C8 108.66(13) . . ?
C1' C7 C8 112.20(13) . . ?
C2' C1' C6' 118.38(16) . . ?
C2' C1' C7 120.42(14) . . ?
C6' C1' C7 121.20(14) . . ?
C5' C6' C1' 120.36(17) . . ?
C4' C5' C6' 120.39(19) . . ?
C3' C4' C5' 119.99(19) . . ?
C4' C3' C2' 119.86(19) . . ?
C3' C2' C1' 120.99(17) . . ?
 
 
_diffrn_measured_fraction_theta_max    0.974
_diffrn_reflns_theta_full              28.01
_diffrn_measured_fraction_theta_full   0.974
_refine_diff_density_max    0.187
_refine_diff_density_min   -0.143
_refine_diff_density_rms    0.036