# Copyright The Royal Society of Chemistry, 1998
# CCDC Number: 207/279


data_1
#=============================================================
_audit_creation_date        'February 22, 1995'
_audit_creation_method
 'from NRCVAX CIF routine and SHELXL93 with Word-Perfect Macro PREPSHEL'
_audit_update_record
;   February 22, 1995  Assembled, pass-1


;

#=====================================================================

# 5. Chemical Data
_chemical_name_systematic
;
 ?  #Insert the chemical name here.
;
_chemical_name_common             ?
_chemical_formula_moiety         'C20 H20 N4 O4 '
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum             'C20 H20 N4 O4'
_chemical_formula_weight          380.40
_chemical_compound_source         'synthesized by the authors'

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'

#==========================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting            Triclinic  
_symmetry_space_group_name_H-M    'P -1'

loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                    7.943(5)
_cell_length_b                    8.000(3)
_cell_length_c                    16.237(3)
_cell_angle_alpha                 101.63(2)
_cell_angle_beta                  93.12(3)
_cell_angle_gamma                 112.79(3)
_cell_volume                      921.6(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     294(1)

_cell_measurement_reflns_used      25
_cell_measurement_theta_min         5.30
_cell_measurement_theta_max        13.35
_cell_special_details
;
 ?  #Insert any comments here.
;
_exptl_crystal_description        plate
_exptl_crystal_colour             reddish-orange
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.40
_exptl_crystal_size_min           0.04
_exptl_crystal_size_rad           ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.371
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              400
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   1.0000
_exptl_absorpt_correction_T_max   1.0000

#==========================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details
;
 ?  #Insert any special details here.
;

_diffrn_ambient_temperature     294(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Molybdenum K\a'
_diffrn_radiation_source         'X-ray tube'

_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Nonius CAD-4    '
_diffrn_measurement_method       'Theta/2theta scan b/P/b '
_diffrn_standards_number           3
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%         2.0
loop_
     _diffrn_standard_refln_index_h
     _diffrn_standard_refln_index_k
     _diffrn_standard_refln_index_l
      0   0   8
      1  -3   4
      2  -1   4

_diffrn_reflns_number             3248
_diffrn_reflns_av_R_equivalents   0.0
_diffrn_reflns_av_sigmaI/netI     0.1091
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2
_diffrn_reflns_theta_max          25
_reflns_number_total              3248
_reflns_number_observed           1274
_reflns_observed_criterion        >2\s(I)

_computing_data_collection        'Enraf-Nonius CAD4 (Enraf-Nonius 1992)'
_computing_cell_refinement        'Enraf-Nonius SET4 and CELDIM'
_computing_data_reduction       
          'DATRD2 in NRCVAX94 (Gabe, Le Page, Charland, Lee & White, 1989)'
_computing_structure_solution     'SHELXS86 (Sheldrick, 1986)'
_computing_structure_refinement   'NRCVAX94 and SHELXL93 (Sheldrick, 1993)'
_computing_molecular_graphics   
          'NRCVAX94, PLATON (Spek, 1994a) and PLUTON (Spek 1994b)'
_computing_publication_material   'NRCVAX94, SHELXL93  and WordPerfect'

#=========================================================================

# 8. Refinement Data

_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme
 'calc w=1/[\s^2^(Fo^2^)+(0.0649P)^2^] 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 (SHELXL defaults, C-H 0.93 to 0.98, N-H 0.86\%A)'
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3248
_refine_ls_number_parameters      253
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1577
_refine_ls_R_factor_obs           0.0541
_refine_ls_wR_factor_all          0.1376
_refine_ls_wR_factor_obs          0.1152
_refine_ls_goodness_of_fit_all    0.835
_refine_ls_goodness_of_fit_obs    1.192
_refine_ls_restrained_S_all       0.835
_refine_ls_restrained_S_obs       1.192
_refine_ls_shift/esd_max          0.000
_refine_ls_shift/esd_mean         0.000
_refine_diff_density_max          0.164
_refine_diff_density_min         -0.212

#=========================================================================

# 9. Atomic Coordinates and Thermal Parameters

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 0.2635(4) 0.1160(3) 0.4306(2) 0.0879(10) Uani 1 d . .
O2 O 0.1907(4) 0.0544(3) 0.5497(2) 0.0777(9) Uani 1 d . .
O3 O 0.0614(4) 0.4668(4) 0.7624(2) 0.0893(9) Uani 1 d . .
O4 O 0.0761(4) 0.7293(4) 0.7426(2) 0.0853(9) Uani 1 d . .
N1 N 0.3681(4) 0.5853(3) 0.3612(2) 0.0485(7) Uani 1 d . .
N2 N 0.3170(4) 0.4414(3) 0.40276(15) 0.0487(8) Uani 1 d . .
N3 N 0.2221(4) 0.1582(4) 0.5014(2) 0.0584(8) Uani 1 d . .
N4 N 0.0917(4) 0.5826(4) 0.7202(2) 0.0585(8) Uani 1 d . .
C1 C 0.4087(5) 0.5535(4) 0.2861(2) 0.0489(9) Uani 1 d . .
C2 C 0.4642(5) 0.7151(4) 0.2456(2) 0.0541(10) Uani 1 d . .
C3 C 0.4603(6) 0.6749(5) 0.1507(2) 0.0645(11) Uani 1 d . .
C4 C 0.3992(6) 0.4751(5) 0.0987(2) 0.0699(12) Uani 1 d . .
C5 C 0.2905(5) 0.3281(4) 0.1436(2) 0.0573(10) Uani 1 d . .
C6 C 0.3921(5) 0.3678(4) 0.2326(2) 0.0578(10) Uani 1 d . .
C7 C 0.4197(6) 0.8752(5) 0.2877(2) 0.0726(12) Uani 1 d . .
C8 C 0.6419(6) 0.7639(5) 0.2083(2) 0.0744(12) Uani 1 d . .
C11 C 0.2630(4) 0.4716(4) 0.4794(2) 0.0379(8) Uani 1 d . .
C12 C 0.2157(4) 0.3389(4) 0.5290(2) 0.0420(8) Uani 1 d . .
C13 C 0.1585(4) 0.3740(4) 0.6071(2) 0.0471(9) Uani 1 d . .
C14 C 0.1503(4) 0.5433(4) 0.6376(2) 0.0427(8) Uani 1 d . .
C15 C 0.1963(5) 0.6758(4) 0.5908(2) 0.0478(9) Uani 1 d . .
C16 C 0.2528(4) 0.6429(4) 0.5138(2) 0.0438(9) Uani 1 d . .
C21 C 0.2391(5) 0.1276(5) 0.0941(2) 0.0555(10) Uani 1 d . .
C22 C 0.2992(6) 0.0832(6) 0.0189(2) 0.0889(14) Uani 1 d . .
C23 C 0.2421(7) -0.1016(6) -0.0266(2) 0.094(2) Uani 1 d . .
C24 C 0.1292(6) -0.2417(6) 0.0034(2) 0.0781(13) Uani 1 d . .
C25 C 0.0671(7) -0.2010(6) 0.0790(3) 0.0911(15) Uani 1 d . .
C26 C 0.1227(6) -0.0178(5) 0.1233(2) 0.0790(13) Uani 1 d . .
H2 H 0.3198 0.3358 0.38010 0.058 Uiso 1 calc R .
H3 H 0.4286 0.7581 0.1223 0.077 Uiso 1 calc R .
H4A H 0.3240 0.4592 0.0462 0.084 Uiso 1 calc R .
H4B H 0.5077 0.4551 0.0839 0.084 Uiso 1 calc R .
H5 H 0.1744 0.3415 0.1510 0.069 Uiso 1 calc R .
H6A H 0.3256 0.2688 0.2597 0.069 Uiso 1 calc R .
H6B H 0.5144 0.3701 0.2286 0.069 Uiso 1 calc R .
H7A H 0.4622 0.9725 0.2578 0.109 Uiso 1 calc R .
H7B H 0.4799 0.9228 0.3455 0.109 Uiso 1 calc R .
H7C H 0.2886 0.8327 0.2866 0.109 Uiso 1 calc R .
H8A H 0.7170 0.8949 0.2126 0.089 Uiso 1 calc R .
H8B H 0.7109 0.6881 0.2122 0.089 Uiso 1 calc R .
H13 H 0.1259 0.2841 0.6386 0.057 Uiso 1 calc R .
H15 H 0.1886 0.7892 0.6119 0.057 Uiso 1 calc R .
H16 H 0.2852 0.7350 0.4835 0.053 Uiso 1 calc R .
H22 H 0.3801 0.1786 -0.0024 0.107 Uiso 1 calc R .
H23 H 0.2829 -0.1277 -0.0784 0.113 Uiso 1 calc R .
H24 H 0.0931 -0.3651 -0.0266 0.094 Uiso 1 calc R .
H25 H -0.0124 -0.2970 0.1004 0.109 Uiso 1 calc R .
H26 H 0.0799 0.0077 0.1745 0.095 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
O1 0.138(3) 0.056(2) 0.090(2) 0.0210(14) 0.055(2) 0.053(2)
O2 0.112(2) 0.0464(14) 0.086(2) 0.0328(14) 0.013(2) 0.0358(15)
O3 0.122(3) 0.102(2) 0.071(2) 0.050(2) 0.044(2) 0.056(2)
O4 0.117(3) 0.070(2) 0.071(2) 0.0085(14) 0.041(2) 0.041(2)
N1 0.056(2) 0.042(2) 0.046(2) 0.0160(13) 0.0113(15) 0.0155(15)
N2 0.066(2) 0.041(2) 0.038(2) 0.0083(13) 0.0081(15) 0.021(2)
N3 0.064(2) 0.045(2) 0.070(2) 0.016(2) 0.010(2) 0.025(2)
N4 0.059(2) 0.064(2) 0.052(2) 0.012(2) 0.014(2) 0.025(2)
C1 0.050(2) 0.050(2) 0.045(2) 0.009(2) 0.009(2) 0.020(2)
C2 0.063(3) 0.049(2) 0.051(2) 0.021(2) 0.014(2) 0.019(2)
C3 0.079(3) 0.066(3) 0.050(2) 0.026(2) 0.013(2) 0.024(2)
C4 0.084(3) 0.070(3) 0.053(2) 0.024(2) 0.017(2) 0.023(2)
C5 0.070(3) 0.060(2) 0.039(2) 0.011(2) 0.009(2) 0.024(2)
C6 0.075(3) 0.061(2) 0.041(2) 0.013(2) 0.007(2) 0.033(2)
C7 0.097(3) 0.056(2) 0.072(3) 0.024(2) 0.021(2) 0.032(2)
C8 0.071(3) 0.073(3) 0.077(3) 0.033(2) 0.024(3) 0.018(2)
C11 0.037(2) 0.034(2) 0.035(2) 0.0035(14) -0.005(2) 0.011(2)
C12 0.045(2) 0.031(2) 0.050(2) 0.011(2) 0.003(2) 0.014(2)
C13 0.043(2) 0.049(2) 0.049(2) 0.020(2) 0.002(2) 0.015(2)
C14 0.041(2) 0.048(2) 0.037(2) 0.011(2) 0.006(2) 0.016(2)
C15 0.055(3) 0.036(2) 0.047(2) 0.008(2) 0.006(2) 0.014(2)
C16 0.048(2) 0.036(2) 0.046(2) 0.014(2) 0.005(2) 0.014(2)
C21 0.068(3) 0.059(2) 0.043(2) 0.011(2) 0.013(2) 0.029(2)
C22 0.124(4) 0.077(3) 0.061(3) 0.015(2) 0.038(3) 0.033(3)
C23 0.137(5) 0.091(3) 0.054(3) 0.006(3) 0.025(3) 0.050(3)
C24 0.100(4) 0.067(3) 0.064(3) -0.001(2) -0.004(3) 0.040(3)
C25 0.115(4) 0.063(3) 0.079(3) 0.006(2) 0.024(3) 0.023(3)
C26 0.099(4) 0.067(3) 0.060(3) 0.007(2) 0.023(2) 0.025(3)

#=========================================================================

# 10. Molecular Geometry

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 N3 1.232(3) . ?
O2 N3 1.220(3) . ?
O3 N4 1.219(3) . ?
O4 N4 1.212(3) . ?
N1 C1 1.279(4) . ?
N1 N2 1.388(3) . ?
N2 C11 1.345(3) . ?
N2 H2 0.86 . ?
N2 O1 2.608(4) . ?
H2 O1 1.99 . ?
N3 C12 1.446(4) . ?
N4 C14 1.458(4) . ?
C1 C2 1.494(4) . ?
C1 C6 1.515(4) . ?
C2 C3 1.506(4) . ?
C2 C7 1.502(4) . ?
C2 C8 1.508(5) . ?
C3 C4 1.520(4) . ?
C3 C8 1.501(5) . ?
C4 C5 1.513(4) . ?
C5 C6 1.526(4) . ?
C5 C21 1.524(4) . ?
C11 C12 1.408(4) . ?
C11 C16 1.407(4) . ?
C12 C13 1.382(4) . ?
C13 C14 1.373(4) . ?
C14 C15 1.375(4) . ?
C15 C16 1.361(4) . ?
C21 C22 1.365(5) . ?
C21 C26 1.368(5) . ?
C22 C23 1.394(5) . ?
C23 C24 1.336(5) . ?
C24 C25 1.374(5) . ?
C25 C26 1.378(5) . ?

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C1 N1 N2 118.4(3) . . ?
C11 N2 N1 118.2(3) . . ?
O2 N3 O1 122.1(3) . . ?
O2 N3 C12 119.1(3) . . ?
O1 N3 C12 118.7(3) . . ?
O4 N4 O3 124.1(3) . . ?
O4 N4 C14 117.6(3) . . ?
O3 N4 C14 118.3(3) . . ?
N1 C1 C2 115.5(3) . . ?
N1 C1 C6 126.9(3) . . ?
C2 C1 C6 117.4(3) . . ?
C1 C2 C7 115.7(3) . . ?
C1 C2 C3 117.8(3) . . ?
C7 C2 C3 118.2(3) . . ?
C1 C2 C8 117.1(3) . . ?
C7 C2 C8 116.8(3) . . ?
C3 C2 C8 59.7(2) . . ?
C8 C3 C2 60.2(2) . . ?
C8 C3 C4 118.4(4) . . ?
C2 C3 C4 120.4(3) . . ?
C5 C4 C3 114.2(3) . . ?
C4 C5 C6 110.0(3) . . ?
C4 C5 C21 114.4(3) . . ?
C6 C5 C21 111.8(3) . . ?
C1 C6 C5 110.7(3) . . ?
C3 C8 C2 60.1(2) . . ?
N2 C11 C16 119.9(3) . . ?
N2 C11 C12 123.2(3) . . ?
C16 C11 C12 116.9(3) . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 N3 116.0(3) . . ?
C11 C12 N3 122.4(3) . . ?
C14 C13 C12 119.2(3) . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 N4 119.7(3) . . ?
C15 C14 N4 119.7(3) . . ?
C16 C15 C14 120.8(3) . . ?
C15 C16 C11 121.0(3) . . ?
C22 C21 C26 116.9(4) . . ?
C22 C21 C5 123.2(3) . . ?
C26 C21 C5 119.9(3) . . ?
C21 C22 C23 121.5(4) . . ?
C24 C23 C22 120.5(4) . . ?
C23 C24 C25 119.1(4) . . ?
C24 C25 C26 120.0(4) . . ?
C21 C26 C25 121.9(4) . . ?
N2 H2 O1 127.4 . . ?

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
 C1 N1 N2 C11 -175.8(3) . . . . ?
 N2 N1 C1 C2 -179.4(3) . . . . ?
 N2 N1 C1 C6 5.7(5) . . . . ?
 N1 C1 C2 C7 -14.8(5) . . . . ?
 C6 C1 C2 C7 160.6(3) . . . . ?
 N1 C1 C2 C3 -162.7(3) . . . . ?
 C6 C1 C2 C3 12.7(5) . . . . ?
 N1 C1 C2 C8 129.1(4) . . . . ?
 C6 C1 C2 C8 -55.5(4) . . . . ?
 C1 C2 C3 C8 -106.7(4) . . . . ?
 C7 C2 C3 C8 106.2(4) . . . . ?
 C8 C2 C3 C8 0.000(1) . . . . ?
 C1 C2 C3 C4 0.8(6) . . . . ?
 C7 C2 C3 C4 -146.3(4) . . . . ?
 C8 C2 C3 C4 107.5(4) . . . . ?
 C8 C3 C4 C5 88.7(4) . . . . ?
 C2 C3 C4 C5 18.4(6) . . . . ?
 C3 C4 C5 C6 -49.6(5) . . . . ?
 C3 C4 C5 C21 -176.4(3) . . . . ?
 N1 C1 C6 C5 130.4(4) . . . . ?
 C2 C1 C6 C5 -44.4(4) . . . . ?
 C4 C5 C6 C1 62.7(4) . . . . ?
 C21 C5 C6 C1 -169.0(3) . . . . ?
 C2 C3 C8 C2 0.000(1) . . . . ?
 C4 C3 C8 C2 -110.6(3) . . . . ?
 C1 C2 C8 C3 107.9(4) . . . . ?
 C7 C2 C8 C3 -108.6(3) . . . . ?
 N1 N2 C11 C16 2.4(4) . . . . ?
 N1 N2 C11 C12 -177.2(3) . . . . ?
 N2 C11 C12 C13 -179.1(3) . . . . ?
 C16 C11 C12 C13 1.2(4) . . . . ?
 N2 C11 C12 N3 0.3(5) . . . . ?
 C16 C11 C12 N3 -179.4(3) . . . . ?
 O2 N3 C12 C13 -5.2(4) . . . . ?
 O1 N3 C12 C13 176.6(3) . . . . ?
 O2 N3 C12 C11 175.4(3) . . . . ?
 O1 N3 C12 C11 -2.8(5) . . . . ?
 C11 C12 C13 C14 -1.0(5) . . . . ?
 N3 C12 C13 C14 179.6(3) . . . . ?
 C12 C13 C14 C15 0.8(5) . . . . ?
 C12 C13 C14 N4 -179.5(3) . . . . ?
 O4 N4 C14 C13 -175.8(3) . . . . ?
 O3 N4 C14 C13 4.1(5) . . . . ?
 O4 N4 C14 C15 3.9(5) . . . . ?
 O3 N4 C14 C15 -176.1(3) . . . . ?
 C13 C14 C15 C16 -0.8(5) . . . . ?
 N4 C14 C15 C16 179.4(3) . . . . ?
 C14 C15 C16 C11 1.0(5) . . . . ?
 N2 C11 C16 C15 179.1(3) . . . . ?
 C12 C11 C16 C15 -1.2(4) . . . . ?
 C4 C5 C21 C22 5.5(5) . . . . ?
 C6 C5 C21 C22 -120.3(4) . . . . ?
 C4 C5 C21 C26 -172.3(4) . . . . ?
 C6 C5 C21 C26 61.8(5) . . . . ?
 C26 C21 C22 C23 1.0(6) . . . . ?
 C5 C21 C22 C23 -176.8(4) . . . . ?
 C21 C22 C23 C24 -1.5(7) . . . . ?
 C22 C23 C24 C25 1.3(7) . . . . ?
 C23 C24 C25 C26 -0.6(7) . . . . ?
 C22 C21 C26 C25 -0.4(6) . . . . ?
 C5 C21 C26 C25 177.6(4) . . . . ?
 C24 C25 C26 C21 0.2(7) . . . . ?