# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2001
# CCDC Numbers: 155368,155369

data_global

loop_
_publ_author_name

'Bobosikova, Maria'
'Clegg, W.'
'Coles, Simon J.'
'Dandarova, Miloslava'
'Hursthouse, Michael B.'
'Kiss, Tibor'
'Krutosikova, Alzbeta'
'Liptaj, Tibor'
'Pronayova, N.'
'Ramsden, C. A.'

_journal_coden_Cambridge   207

_publ_contact_author
;Prof C A Ramsden
Department of Chemistry
Keele University
Keele
STAFFS
ST5 5BG
UK
;

data_s92_15b 
_database_code_CSD             155638
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
'C25 H17 N3 O2' 
_chemical_formula_weight          391.42 

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                    15.508(2) 
_cell_length_b                    3.832(4) 
_cell_length_c                    30.909(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  92.30(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1835.3(19) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     12000
_cell_measurement_theta_min       2.25
_cell_measurement_theta_max       29.41

_exptl_crystal_description        needle
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.30 
_exptl_crystal_size_mid           0.02 
_exptl_crystal_size_min           0.02 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.417 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              816 
_exptl_absorpt_coefficient_mu     0.092 
_exptl_absorpt_correction_type    'multi-scans'
_exptl_absorpt_correction_T_min   0.9729 
_exptl_absorpt_correction_T_max   0.9982 
_exptl_absorpt_process_details    ? 

_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       150(2) 
_diffrn_radiation_wavelength      0.68750 
_diffrn_radiation_type            synchrotron
_diffrn_radiation_source          synchrotron
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker SMART CCD'
_diffrn_measurement_method        'phi scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             12000 
_diffrn_reflns_av_R_equivalents   0.0446 
_diffrn_reflns_av_sigmaI/netI     0.0569 
_diffrn_reflns_limit_h_min        -21 
_diffrn_reflns_limit_h_max        18 
_diffrn_reflns_limit_k_min        -5 
_diffrn_reflns_limit_k_max        3 
_diffrn_reflns_limit_l_min        -43 
_diffrn_reflns_limit_l_max        42 
_diffrn_reflns_theta_min          2.25 
_diffrn_reflns_theta_max          29.41 
_reflns_number_total              5143 
_reflns_number_gt                 4019 
_reflns_threshold_expression      >2sigma(I) 

_computing_data_collection        SMART
_computing_cell_refinement        SMART
_computing_data_reduction         SAINT
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     CAMERON
_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^)+(0.0899P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          5143 
_refine_ls_number_parameters      272 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0624 
_refine_ls_R_factor_gt            0.0507 
_refine_ls_wR_factor_ref          0.1371 
_refine_ls_wR_factor_gt           0.1316 
_refine_ls_goodness_of_fit_ref    0.981 
_refine_ls_restrained_S_all       0.981 
_refine_ls_shift/su_max           0.027 
_refine_ls_shift/su_mean          0.000 

loop_ 
_atom_site_label 
_atom_site_type_symbol 
_atom_site_fract_x 
_atom_site_fract_y 
_atom_site_fract_z 
_atom_site_U_iso_or_equiv 
_atom_site_adp_type 
_atom_site_occupancy 
_atom_site_symmetry_multiplicity 
_atom_site_calc_flag 
_atom_site_refinement_flags 
_atom_site_disorder_assembly 
_atom_site_disorder_group 
O1 O 0.67740(5) -0.1155(3) 0.06819(3) 0.0226(2) Uani 1 1 d . . . 
O2 O 0.52251(5) 0.0677(2) 0.20913(3) 0.02024(19) Uani 1 1 d . . . 
N1 N 0.43969(6) -0.3098(3) 0.10938(3) 0.0178(2) Uani 1 1 d . . . 
N2 N 0.40176(6) -0.5156(3) 0.04036(3) 0.0209(2) Uani 1 1 d . . . 
H2 H 0.4200 -0.5723 0.0147 0.025 Uiso 1 1 calc R . . 
N3 N 0.54099(6) -0.3293(3) 0.05223(3) 0.0199(2) Uani 1 1 d . . . 
C1 C 0.80479(8) 0.1288(4) 0.10551(4) 0.0258(3) Uani 1 1 d . . . 
H1 H 0.8390 0.1084 0.0808 0.031 Uiso 1 1 calc R . . 
C2 C 0.83803(8) 0.2629(4) 0.14453(4) 0.0277(3) Uani 1 1 d . . . 
H2A H 0.8966 0.3362 0.1469 0.033 Uiso 1 1 calc R . . 
C3 C 0.78643(8) 0.2910(4) 0.18021(4) 0.0269(3) Uani 1 1 d . . . 
H3 H 0.8107 0.3831 0.2065 0.032 Uiso 1 1 calc R . . 
C4 C 0.70051(8) 0.1884(4) 0.17845(4) 0.0240(3) Uani 1 1 d . . . 
H4 H 0.6663 0.2111 0.2031 0.029 Uiso 1 1 calc R . . 
C5 C 0.66527(7) 0.0509(3) 0.13968(4) 0.0186(2) Uani 1 1 d . . . 
C6 C 0.71953(7) 0.0271(3) 0.10458(4) 0.0206(2) Uani 1 1 d . . . 
C7 C 0.59553(7) -0.1862(3) 0.08026(4) 0.0182(2) Uani 1 1 d . . . 
C8 C 0.58270(7) -0.0893(3) 0.12352(3) 0.0171(2) Uani 1 1 d . . . 
C9 C 0.49922(7) -0.1636(3) 0.13663(3) 0.0168(2) Uani 1 1 d . . . 
C10 C 0.46162(7) -0.3812(3) 0.06879(3) 0.0175(2) Uani 1 1 d . . . 
C11 C 0.31318(7) -0.5754(3) 0.04723(3) 0.0174(2) Uani 1 1 d . . . 
C12 C 0.25420(7) -0.4919(3) 0.01383(4) 0.0208(2) Uani 1 1 d . . . 
H12 H 0.2736 -0.3857 -0.0118 0.025 Uiso 1 1 calc R . . 
C13 C 0.16702(8) -0.5629(4) 0.01773(4) 0.0237(3) Uani 1 1 d . . . 
H13 H 0.1275 -0.5071 -0.0055 0.028 Uiso 1 1 calc R . . 
C14 C 0.13673(7) -0.7139(3) 0.05501(4) 0.0220(3) Uani 1 1 d . . . 
C15 C 0.19655(8) -0.7936(3) 0.08832(4) 0.0209(2) Uani 1 1 d . . . 
H15 H 0.1769 -0.8956 0.1142 0.025 Uiso 1 1 calc R . . 
C16 C 0.28392(8) -0.7283(3) 0.08486(4) 0.0198(2) Uani 1 1 d . . . 
H16 H 0.3235 -0.7873 0.1079 0.024 Uiso 1 1 calc R . . 
C17 C 0.04213(8) -0.7947(4) 0.05942(5) 0.0328(3) Uani 1 1 d . . . 
H17A H 0.0351 -1.0438 0.0655 0.049 Uiso 1 1 calc R . . 
H17B H 0.0103 -0.7353 0.0324 0.049 Uiso 1 1 calc R . . 
H17C H 0.0197 -0.6574 0.0832 0.049 Uiso 1 1 calc R . . 
C18 C 0.46693(7) -0.0928(3) 0.17934(3) 0.0175(2) Uani 1 1 d . . . 
C19 C 0.38903(7) -0.1616(3) 0.19618(3) 0.0190(2) Uani 1 1 d . . . 
H19 H 0.3408 -0.2704 0.1818 0.023 Uiso 1 1 calc R . . 
C20 C 0.39426(7) -0.0367(3) 0.24003(3) 0.0183(2) Uani 1 1 d . . . 
C21 C 0.47706(7) 0.1014(3) 0.24620(3) 0.0189(2) Uani 1 1 d . . . 
C22 C 0.50863(8) 0.2510(3) 0.28432(4) 0.0236(3) Uani 1 1 d . . . 
H22 H 0.5653 0.3447 0.2872 0.028 Uiso 1 1 calc R . . 
C23 C 0.45245(9) 0.2560(4) 0.31815(4) 0.0261(3) Uani 1 1 d . . . 
H23 H 0.4710 0.3556 0.3451 0.031 Uiso 1 1 calc R . . 
C24 C 0.36886(9) 0.1173(3) 0.31341(4) 0.0257(3) Uani 1 1 d . . . 
H24 H 0.3321 0.1242 0.3373 0.031 Uiso 1 1 calc R . . 
C25 C 0.33879(8) -0.0291(3) 0.27490(4) 0.0223(2) Uani 1 1 d . . . 
H25 H 0.2821 -0.1223 0.2720 0.027 Uiso 1 1 calc R . . 

loop_ 
_atom_site_aniso_label 
_atom_site_aniso_U_11 
_atom_site_aniso_U_22 
_atom_site_aniso_U_33 
_atom_site_aniso_U_23 
_atom_site_aniso_U_13 
_atom_site_aniso_U_12 
O1 0.0195(4) 0.0305(5) 0.0179(4) -0.0015(3) 0.0044(3) -0.0031(3) 
O2 0.0211(4) 0.0257(5) 0.0140(4) -0.0056(3) 0.0018(3) -0.0001(3) 
N1 0.0206(4) 0.0203(5) 0.0127(4) -0.0018(4) 0.0020(3) 0.0013(4) 
N2 0.0202(5) 0.0310(6) 0.0117(4) -0.0056(4) 0.0037(3) -0.0029(4) 
N3 0.0208(5) 0.0249(6) 0.0143(4) -0.0016(4) 0.0038(3) -0.0007(4) 
C1 0.0217(6) 0.0277(7) 0.0281(6) 0.0027(5) 0.0025(4) -0.0025(5) 
C2 0.0220(6) 0.0257(7) 0.0353(7) 0.0026(5) -0.0019(5) -0.0040(5) 
C3 0.0265(6) 0.0268(7) 0.0271(6) -0.0029(5) -0.0051(5) -0.0036(5) 
C4 0.0258(6) 0.0246(7) 0.0215(6) -0.0030(5) -0.0011(4) -0.0016(5) 
C5 0.0200(5) 0.0168(6) 0.0189(5) 0.0011(4) 0.0000(4) 0.0003(4) 
C6 0.0221(5) 0.0195(6) 0.0202(5) 0.0006(4) 0.0002(4) -0.0005(4) 
C7 0.0187(5) 0.0207(6) 0.0156(5) 0.0015(4) 0.0043(4) 0.0009(4) 
C8 0.0211(5) 0.0170(6) 0.0131(5) -0.0009(4) 0.0012(4) 0.0007(4) 
C9 0.0212(5) 0.0166(5) 0.0127(5) 0.0004(4) 0.0018(4) 0.0021(4) 
C10 0.0206(5) 0.0185(6) 0.0135(5) -0.0007(4) 0.0031(4) 0.0010(4) 
C11 0.0200(5) 0.0179(6) 0.0145(5) -0.0034(4) 0.0037(4) 0.0001(4) 
C12 0.0241(5) 0.0247(6) 0.0139(5) 0.0019(4) 0.0030(4) -0.0001(5) 
C13 0.0227(5) 0.0285(7) 0.0199(6) 0.0031(5) -0.0003(4) 0.0012(5) 
C14 0.0218(5) 0.0212(6) 0.0233(6) -0.0001(5) 0.0049(4) 0.0001(4) 
C15 0.0267(6) 0.0192(6) 0.0173(5) 0.0019(4) 0.0062(4) -0.0008(4) 
C16 0.0239(5) 0.0207(6) 0.0148(5) 0.0002(4) 0.0016(4) 0.0007(4) 
C17 0.0230(6) 0.0375(8) 0.0382(7) 0.0042(6) 0.0061(5) -0.0030(5) 
C18 0.0214(5) 0.0183(6) 0.0128(5) -0.0021(4) 0.0005(4) 0.0005(4) 
C19 0.0229(5) 0.0200(6) 0.0142(5) -0.0021(4) 0.0020(4) -0.0002(4) 
C20 0.0248(5) 0.0165(5) 0.0137(5) -0.0001(4) 0.0016(4) 0.0024(4) 
C21 0.0241(5) 0.0196(6) 0.0131(5) -0.0011(4) 0.0029(4) 0.0044(4) 
C22 0.0272(6) 0.0247(7) 0.0188(5) -0.0048(5) -0.0024(4) 0.0038(5) 
C23 0.0400(7) 0.0237(7) 0.0144(5) -0.0042(5) -0.0002(4) 0.0064(5) 
C24 0.0403(7) 0.0215(6) 0.0159(5) -0.0007(5) 0.0085(5) 0.0055(5) 
C25 0.0289(6) 0.0195(6) 0.0189(5) 0.0005(4) 0.0065(4) 0.0015(5) 

_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 C7 1.3648(13) . ? 
O1 C6 1.3895(14) . ? 
O2 C21 1.3751(13) . ? 
O2 C18 1.3804(14) . ? 
N1 C10 1.3413(14) . ? 
N1 C9 1.3465(15) . ? 
N2 C10 1.3541(15) . ? 
N2 C11 1.4170(14) . ? 
N3 C7 1.3066(15) . ? 
N3 C10 1.3664(14) . ? 
C1 C6 1.3777(16) . ? 
C1 C2 1.3911(19) . ? 
C2 C3 1.3925(19) . ? 
C3 C4 1.3882(17) . ? 
C4 C5 1.4000(16) . ? 
C5 C6 1.4024(16) . ? 
C5 C8 1.4581(16) . ? 
C7 C8 1.4097(15) . ? 
C8 C9 1.4012(15) . ? 
C9 C18 1.4561(15) . ? 
C11 C12 1.3890(16) . ? 
C11 C16 1.3945(16) . ? 
C12 C13 1.3890(16) . ? 
C13 C14 1.3880(17) . ? 
C14 C15 1.3919(17) . ? 
C14 C17 1.5109(16) . ? 
C15 C16 1.3861(16) . ? 
C18 C19 1.3602(15) . ? 
C19 C20 1.4366(15) . ? 
C20 C21 1.3949(17) . ? 
C20 C25 1.4062(15) . ? 
C21 C22 1.3822(16) . ? 
C22 C23 1.3878(18) . ? 
C23 C24 1.403(2) . ? 
C24 C25 1.3799(17) . ? 

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 O1 C6 105.62(9) . . ? 
C21 O2 C18 105.69(9) . . ? 
C10 N1 C9 118.46(10) . . ? 
C10 N2 C11 127.44(9) . . ? 
C7 N3 C10 112.44(9) . . ? 
C6 C1 C2 116.41(12) . . ? 
C1 C2 C3 120.70(12) . . ? 
C4 C3 C2 121.88(12) . . ? 
C3 C4 C5 118.78(12) . . ? 
C4 C5 C6 117.45(11) . . ? 
C4 C5 C8 137.66(11) . . ? 
C6 C5 C8 104.89(10) . . ? 
C1 C6 O1 123.22(11) . . ? 
C1 C6 C5 124.79(11) . . ? 
O1 C6 C5 112.00(10) . . ? 
N3 C7 O1 119.13(10) . . ? 
N3 C7 C8 128.84(10) . . ? 
O1 C7 C8 112.03(10) . . ? 
C9 C8 C7 112.82(10) . . ? 
C9 C8 C5 141.69(10) . . ? 
C7 C8 C5 105.46(10) . . ? 
N1 C9 C8 121.47(10) . . ? 
N1 C9 C18 113.11(10) . . ? 
C8 C9 C18 125.42(10) . . ? 
N1 C10 N2 119.44(10) . . ? 
N1 C10 N3 125.93(11) . . ? 
N2 C10 N3 114.63(10) . . ? 
C12 C11 C16 119.35(10) . . ? 
C12 C11 N2 117.70(10) . . ? 
C16 C11 N2 122.87(10) . . ? 
C11 C12 C13 120.31(11) . . ? 
C14 C13 C12 121.11(11) . . ? 
C13 C14 C15 117.89(11) . . ? 
C13 C14 C17 121.51(12) . . ? 
C15 C14 C17 120.60(11) . . ? 
C16 C15 C14 121.87(11) . . ? 
C15 C16 C11 119.46(11) . . ? 
C19 C18 O2 111.80(10) . . ? 
C19 C18 C9 130.83(11) . . ? 
O2 C18 C9 117.37(10) . . ? 
C18 C19 C20 106.21(10) . . ? 
C21 C20 C25 118.39(10) . . ? 
C21 C20 C19 105.79(10) . . ? 
C25 C20 C19 135.81(11) . . ? 
O2 C21 C22 124.98(11) . . ? 
O2 C21 C20 110.50(10) . . ? 
C22 C21 C20 124.51(11) . . ? 
C21 C22 C23 115.88(12) . . ? 
C22 C23 C24 121.42(12) . . ? 
C25 C24 C23 121.52(11) . . ? 
C24 C25 C20 118.28(11) . . ? 

_diffrn_measured_fraction_theta_max    0.914 
_diffrn_reflns_theta_full              29.41 
_diffrn_measured_fraction_theta_full   0.914 
_refine_diff_density_max    0.395 
_refine_diff_density_min   -0.267 
_refine_diff_density_rms    0.064 

data_s92_23
_database_code_CSD             155639
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
'C20 H15 N3'
_chemical_formula_weight          297.35

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                    25.908(5)
_cell_length_b                    10.067(2)
_cell_length_c                    11.851(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  103.36(3)
_cell_angle_gamma                 90.00
_cell_volume                      3007.3(10)
_cell_formula_units_Z             8
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     20181
_cell_measurement_theta_min       2.18
_cell_measurement_theta_max       27.52

_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.4
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.314
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1248
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type    multi-scans
_exptl_absorpt_correction_T_min   0.9690
_exptl_absorpt_correction_T_max   0.9960
_exptl_absorpt_process_details    ?

_exptl_special_details
;
?
;

_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'Phi and Omega scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             20181
_diffrn_reflns_av_R_equivalents   0.0579
_diffrn_reflns_av_sigmaI/netI     0.0380
_diffrn_reflns_limit_h_min        -33
_diffrn_reflns_limit_h_max        33
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          2.18
_diffrn_reflns_theta_max          27.52
_reflns_number_total              3426
_reflns_number_gt                 2720
_reflns_threshold_expression      >2sigma(I)

_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin, Pearce 1995)'
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_number_reflns          3426
_refine_ls_number_parameters      209
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0666
_refine_ls_R_factor_gt            0.0515
_refine_ls_wR_factor_ref          0.1500
_refine_ls_wR_factor_gt           0.1375
_refine_ls_goodness_of_fit_ref    1.118
_refine_ls_restrained_S_all       1.118
_refine_ls_shift/su_max           0.007
_refine_ls_shift/su_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_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 0.35536(4) 0.16651(10) 1.15942(8) 0.0249(3) Uani 1 1 d . . .
N2 N 0.29787(4) 0.13637(10) 0.97155(8) 0.0246(3) Uani 1 1 d . . .
N3 N 0.35091(4) 0.03549(10) 1.31639(8) 0.0258(3) Uani 1 1 d . . .
H3 H 0.3335 -0.0230 1.3453 0.031 Uiso 1 1 calc R . .
C1 C 0.35602(5) 0.33355(13) 0.88208(11) 0.0308(3) Uani 1 1 d . . .
H1 H 0.3302 0.2862 0.8299 0.037 Uiso 1 1 calc R . .
C2 C 0.38306(5) 0.43507(14) 0.84249(12) 0.0361(3) Uani 1 1 d . . .
H2 H 0.3756 0.4549 0.7637 0.043 Uiso 1 1 calc R . .
C3 C 0.42117(5) 0.50769(13) 0.91914(12) 0.0349(3) Uani 1 1 d . . .
H3A H 0.4389 0.5767 0.8922 0.042 Uiso 1 1 calc R . .
C4 C 0.43259(5) 0.47662(13) 1.03620(11) 0.0323(3) Uani 1 1 d . . .
H4 H 0.4582 0.5250 1.0880 0.039 Uiso 1 1 calc R . .
C5 C 0.40611(5) 0.37397(12) 1.07642(10) 0.0273(3) Uani 1 1 d . . .
H5 H 0.4144 0.3532 1.1550 0.033 Uiso 1 1 calc R . .
C6 C 0.36714(4) 0.30130(12) 1.00027(10) 0.0248(3) Uani 1 1 d . . .
C7 C 0.33767(4) 0.19451(11) 1.04482(10) 0.0232(3) Uani 1 1 d . . .
C8 C 0.33134(4) 0.07027(11) 1.20386(9) 0.0233(3) Uani 1 1 d . . .
C9 C 0.28546(4) 0.00285(11) 1.13548(9) 0.0231(3) Uani 1 1 d . . .
C10 C 0.27024(4) 0.04191(11) 1.01799(9) 0.0235(3) Uani 1 1 d . . .
C11 C 0.22608(5) -0.02010(12) 0.94512(10) 0.0285(3) Uani 1 1 d . . .
H11 H 0.2158 0.0043 0.8675 0.034 Uiso 1 1 calc R . .
C12 C 0.19821(5) -0.11592(13) 0.98766(11) 0.0302(3) Uani 1 1 d . . .
H12 H 0.1690 -0.1558 0.9388 0.036 Uiso 1 1 calc R . .
C13 C 0.21327(5) -0.15431(13) 1.10402(11) 0.0290(3) Uani 1 1 d . . .
H13 H 0.1940 -0.2191 1.1322 0.035 Uiso 1 1 calc R . .
C14 C 0.25644(5) -0.09685(12) 1.17683(10) 0.0262(3) Uani 1 1 d . . .
H14 H 0.2666 -0.1239 1.2538 0.031 Uiso 1 1 calc R . .
C15 C 0.39775(5) 0.08730(11) 1.39073(10) 0.0250(3) Uani 1 1 d . . .
C16 C 0.39725(5) 0.11383(12) 1.50575(10) 0.0292(3) Uani 1 1 d . . .
H16 H 0.3664 0.1002 1.5318 0.035 Uiso 1 1 calc R . .
C17 C 0.44258(5) 0.16051(13) 1.58148(11) 0.0356(3) Uani 1 1 d . . .
H17 H 0.4422 0.1772 1.6585 0.043 Uiso 1 1 calc R . .
C18 C 0.48843(5) 0.18249(13) 1.54335(12) 0.0369(3) Uani 1 1 d . . .
H18 H 0.5186 0.2159 1.5938 0.044 Uiso 1 1 calc R . .
C19 C 0.48905(5) 0.15440(13) 1.42937(12) 0.0341(3) Uani 1 1 d . . .
H19 H 0.5200 0.1679 1.4037 0.041 Uiso 1 1 calc R . .
C20 C 0.44420(5) 0.10642(12) 1.35321(11) 0.0294(3) Uani 1 1 d . . .
H20 H 0.4451 0.0870 1.2770 0.035 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 0.0291(5) 0.0236(6) 0.0219(5) 0.0002(4) 0.0060(4) -0.0012(4)
N2 0.0268(5) 0.0251(5) 0.0225(5) 0.0001(4) 0.0072(4) -0.0010(4)
N3 0.0280(5) 0.0272(6) 0.0222(5) 0.0020(4) 0.0056(4) -0.0047(4)
C1 0.0325(7) 0.0302(7) 0.0284(6) 0.0023(5) 0.0042(5) -0.0050(5)
C2 0.0391(7) 0.0373(8) 0.0324(7) 0.0089(6) 0.0089(6) -0.0055(6)
C3 0.0315(7) 0.0295(7) 0.0445(8) 0.0091(6) 0.0100(6) -0.0041(5)
C4 0.0271(6) 0.0274(7) 0.0404(7) -0.0002(5) 0.0037(5) -0.0039(5)
C5 0.0276(6) 0.0265(7) 0.0275(6) 0.0003(5) 0.0059(5) 0.0018(5)
C6 0.0267(6) 0.0225(6) 0.0263(6) 0.0009(5) 0.0085(5) 0.0024(4)
C7 0.0257(6) 0.0219(6) 0.0229(6) -0.0013(4) 0.0071(5) 0.0025(4)
C8 0.0257(6) 0.0223(6) 0.0232(6) -0.0012(4) 0.0082(5) 0.0024(4)
C9 0.0253(6) 0.0220(6) 0.0233(6) -0.0021(5) 0.0080(5) 0.0025(4)
C10 0.0250(6) 0.0234(6) 0.0232(6) -0.0008(5) 0.0083(5) 0.0017(4)
C11 0.0292(6) 0.0320(7) 0.0236(6) 0.0001(5) 0.0050(5) -0.0007(5)
C12 0.0274(6) 0.0310(7) 0.0311(6) -0.0024(5) 0.0048(5) -0.0035(5)
C13 0.0295(6) 0.0264(7) 0.0326(6) 0.0012(5) 0.0100(5) -0.0036(5)
C14 0.0284(6) 0.0270(7) 0.0246(6) 0.0013(5) 0.0089(5) 0.0012(5)
C15 0.0273(6) 0.0208(6) 0.0253(6) 0.0024(4) 0.0026(5) 0.0008(4)
C16 0.0334(7) 0.0265(7) 0.0273(6) 0.0015(5) 0.0062(5) -0.0010(5)
C17 0.0452(8) 0.0298(7) 0.0274(6) -0.0010(5) -0.0006(6) 0.0004(6)
C18 0.0332(7) 0.0272(7) 0.0432(8) -0.0002(6) -0.0060(6) -0.0036(5)
C19 0.0281(6) 0.0280(7) 0.0450(8) 0.0052(6) 0.0058(6) -0.0003(5)
C20 0.0317(7) 0.0277(7) 0.0295(6) 0.0031(5) 0.0089(5) 0.0011(5)

_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 C8 1.3248(15) . ?
N1 C7 1.3587(15) . ?
N2 C7 1.3214(16) . ?
N2 C10 1.3790(15) . ?
N3 C8 1.3585(15) . ?
N3 C15 1.4236(15) . ?
C1 C2 1.3810(18) . ?
C1 C6 1.4013(16) . ?
C2 C3 1.3856(19) . ?
C3 C4 1.3857(18) . ?
C4 C5 1.3845(18) . ?
C5 C6 1.3956(17) . ?
C6 C7 1.4845(17) . ?
C8 C9 1.4440(16) . ?
C9 C14 1.4083(16) . ?
C9 C10 1.4124(16) . ?
C10 C11 1.4100(16) . ?
C11 C12 1.3691(17) . ?
C12 C13 1.3980(18) . ?
C13 C14 1.3726(18) . ?
C15 C20 1.3894(18) . ?
C15 C16 1.3919(17) . ?
C16 C17 1.3852(19) . ?
C17 C18 1.383(2) . ?
C18 C19 1.384(2) . ?
C19 C20 1.3833(19) . ?

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
C8 N1 C7 117.91(10) . . ?
C7 N2 C10 116.19(9) . . ?
C8 N3 C15 125.77(10) . . ?
C2 C1 C6 120.51(12) . . ?
C1 C2 C3 120.55(12) . . ?
C2 C3 C4 119.49(12) . . ?
C5 C4 C3 120.33(11) . . ?
C4 C5 C6 120.70(11) . . ?
C5 C6 C1 118.41(11) . . ?
C5 C6 C7 120.28(10) . . ?
C1 C6 C7 121.29(11) . . ?
N2 C7 N1 126.64(11) . . ?
N2 C7 C6 118.32(10) . . ?
N1 C7 C6 115.04(10) . . ?
N1 C8 N3 118.40(10) . . ?
N1 C8 C9 121.47(10) . . ?
N3 C8 C9 120.13(10) . . ?
C14 C9 C10 119.44(11) . . ?
C14 C9 C8 125.18(10) . . ?
C10 C9 C8 115.37(10) . . ?
N2 C10 C11 118.91(10) . . ?
N2 C10 C9 122.21(10) . . ?
C11 C10 C9 118.86(11) . . ?
C12 C11 C10 120.58(11) . . ?
C11 C12 C13 120.48(11) . . ?
C14 C13 C12 120.32(11) . . ?
C13 C14 C9 120.30(11) . . ?
C20 C15 C16 119.43(12) . . ?
C20 C15 N3 122.02(10) . . ?
C16 C15 N3 118.49(11) . . ?
C17 C16 C15 120.09(12) . . ?
C18 C17 C16 120.42(12) . . ?
C17 C18 C19 119.40(12) . . ?
C20 C19 C18 120.72(12) . . ?
C19 C20 C15 119.92(11) . . ?

_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              27.52
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.370
_refine_diff_density_min   -0.259
_refine_diff_density_rms    0.060