 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H20 N4 O2'
_chemical_formula_weight          324.38
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 '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    Pbca
_symmetry_space_group_name_hall   '-P 2ac 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'
 
_cell_length_a                    10.6683(3)
_cell_length_b                    10.8869(3)
_cell_length_c                    29.9190(8)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      3474.93(17)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4016
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.240
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1376
_exptl_absorpt_coefficient_mu     0.084
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9835
_exptl_absorpt_correction_T_max   0.9917
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
;
_diffrn_ambient_temperature       120(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        'φ and ω 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             11806
_diffrn_reflns_av_R_equivalents   0.0560
_diffrn_reflns_av_sigmaI/netI     0.0637
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -33
_diffrn_reflns_limit_l_max        35
_diffrn_reflns_theta_min          3.33
_diffrn_reflns_theta_max          25.03
_reflns_number_total              3047
_reflns_number_gt                 2027
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection
' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)'
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0545P)²+0.3280P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3047
_refine_ls_number_parameters      218
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0844
_refine_ls_R_factor_gt            0.0452
_refine_ls_wR_factor_ref          0.1103
_refine_ls_wR_factor_gt           0.0947
_refine_ls_goodness_of_fit_ref    0.966
_refine_ls_restrained_S_all       0.966
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O2 O 0.15087(12) 0.42379(11) 0.02778(4) 0.0274(3) Uani 1 1 d . . .
N2 N 0.15828(14) 0.38625(13) -0.08953(5) 0.0227(4) Uani 1 1 d . . .
O1 O 0.19262(13) 0.56952(11) -0.02320(4) 0.0333(4) Uani 1 1 d . . .
N1 N 0.27535(14) 0.35538(13) -0.15435(5) 0.0234(4) Uani 1 1 d . . .
C16 C 0.17974(17) 0.46304(17) -0.01285(6) 0.0233(4) Uani 1 1 d . . .
N3 N 0.59197(17) 0.38690(17) -0.12344(6) 0.0385(5) Uani 1 1 d . . .
C8 C 0.41511(18) 0.34014(16) -0.00853(7) 0.0246(5) Uani 1 1 d . . .
C10 C 0.35083(17) 0.32274(17) -0.23037(6) 0.0257(5) Uani 1 1 d . . .
C3 C 0.10671(18) 0.28150(17) -0.11474(6) 0.0266(5) Uani 1 1 d . . .
H3A H 0.0141 0.2790 -0.1127 0.032 Uiso 1 1 calc R . .
H3B H 0.1413 0.2027 -0.1038 0.032 Uiso 1 1 calc R . .
C15 C 0.29190(19) 0.33148(18) -0.27150(7) 0.0325(5) Uani 1 1 d . . .
H15 H 0.2386 0.3994 -0.2775 0.039 Uiso 1 1 calc R . .
C17 C 0.14375(19) 0.51738(18) 0.06265(6) 0.0300(5) Uani 1 1 d . . .
H17A H 0.0752 0.5760 0.0561 0.036 Uiso 1 1 calc R . .
H17B H 0.2235 0.5636 0.0643 0.036 Uiso 1 1 calc R . .
C2 C 0.26374(17) 0.43608(17) -0.11583(6) 0.0226(4) Uani 1 1 d . . .
H2 H 0.2455 0.5221 -0.1256 0.027 Uiso 1 1 calc R . .
N4 N 0.46893(16) 0.34982(15) 0.02434(6) 0.0335(4) Uani 1 1 d . . .
C14 C 0.3095(2) 0.24275(19) -0.30405(7) 0.0364(5) Uani 1 1 d . . .
H14 H 0.2687 0.2501 -0.3321 0.044 Uiso 1 1 calc R . .
C5 C 0.34318(17) 0.33342(16) -0.05005(6) 0.0221(4) Uani 1 1 d . . .
H5 H 0.3561 0.2508 -0.0639 0.026 Uiso 1 1 calc R . .
C4 C 0.20059(17) 0.35643(17) -0.04459(6) 0.0228(4) Uani 1 1 d . . .
H4 H 0.1576 0.2809 -0.0333 0.027 Uiso 1 1 calc R . .
C7 C 0.49775(19) 0.40694(17) -0.10670(7) 0.0271(5) Uani 1 1 d . . .
C6 C 0.37913(17) 0.43303(16) -0.08418(6) 0.0229(4) Uani 1 1 d . . .
H6 H 0.3859 0.5138 -0.0685 0.028 Uiso 1 1 calc R . .
C11 C 0.4299(2) 0.22373(19) -0.22261(7) 0.0345(5) Uani 1 1 d . . .
H11 H 0.4724 0.2171 -0.1948 0.041 Uiso 1 1 calc R . .
C9 C 0.3274(2) 0.41593(17) -0.19411(6) 0.0281(5) Uani 1 1 d . . .
H9A H 0.4070 0.4574 -0.1862 0.034 Uiso 1 1 calc R . .
H9B H 0.2680 0.4790 -0.2050 0.034 Uiso 1 1 calc R . .
C1 C 0.14903(18) 0.30759(18) -0.16172(6) 0.0268(5) Uani 1 1 d . . .
H1A H 0.1505 0.2319 -0.1800 0.032 Uiso 1 1 calc R . .
H1B H 0.0946 0.3694 -0.1763 0.032 Uiso 1 1 calc R . .
C13 C 0.38651(19) 0.14378(19) -0.29559(7) 0.0349(5) Uani 1 1 d . . .
H13 H 0.3978 0.0820 -0.3177 0.042 Uiso 1 1 calc R . .
C12 C 0.4472(2) 0.1347(2) -0.25504(7) 0.0386(6) Uani 1 1 d . . .
H12 H 0.5010 0.0670 -0.2493 0.046 Uiso 1 1 calc R . .
C18 C 0.1194(2) 0.4528(2) 0.10565(7) 0.0466(6) Uani 1 1 d . . .
H18A H 0.0380 0.4112 0.1041 0.070 Uiso 1 1 calc R . .
H18B H 0.1186 0.5126 0.1301 0.070 Uiso 1 1 calc R . .
H18C H 0.1855 0.3920 0.1110 0.070 Uiso 1 1 calc R . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O2 C16 1.325(2) . ?
O2 C17 1.460(2) . ?
N2 C4 1.455(2) . ?
N2 C3 1.474(2) . ?
N2 C2 1.476(2) . ?
O1 C16 1.208(2) . ?
N1 C2 1.454(2) . ?
N1 C1 1.461(2) . ?
N1 C9 1.469(2) . ?
C16 C4 1.516(3) . ?
N3 C7 1.144(2) . ?
C8 N4 1.144(2) . ?
C8 C5 1.462(3) . ?
C10 C15 1.385(3) . ?
C10 C11 1.388(3) . ?
C10 C9 1.506(3) . ?
C3 C1 1.503(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C15 C14 1.384(3) . ?
C15 H15 0.9500 . ?
C17 C18 1.489(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C2 C6 1.553(3) . ?
C2 H2 1.0000 . ?
C14 C13 1.378(3) . ?
C14 H14 0.9500 . ?
C5 C6 1.538(3) . ?
C5 C4 1.550(3) . ?
C5 H5 1.0000 . ?
C4 H4 1.0000 . ?
C7 C6 1.461(3) . ?
C6 H6 1.0000 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C13 C12 1.378(3) . ?
C13 H13 0.9500 . ?
C12 H12 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C16 O2 C17 116.27(14) . . ?
C4 N2 C3 114.58(14) . . ?
C4 N2 C2 109.77(14) . . ?
C3 N2 C2 107.22(14) . . ?
C2 N1 C1 104.83(14) . . ?
C2 N1 C9 113.75(14) . . ?
C1 N1 C9 112.72(15) . . ?
O1 C16 O2 124.84(17) . . ?
O1 C16 C4 123.89(17) . . ?
O2 C16 C4 111.22(15) . . ?
N4 C8 C5 177.2(2) . . ?
C15 C10 C11 118.53(18) . . ?
C15 C10 C9 121.22(18) . . ?
C11 C10 C9 120.22(17) . . ?
N2 C3 C1 102.72(14) . . ?
N2 C3 H3A 111.2 . . ?
C1 C3 H3A 111.2 . . ?
N2 C3 H3B 111.2 . . ?
C1 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C14 C15 C10 121.02(19) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
O2 C17 C18 107.26(16) . . ?
O2 C17 H17A 110.3 . . ?
C18 C17 H17A 110.3 . . ?
O2 C17 H17B 110.3 . . ?
C18 C17 H17B 110.3 . . ?
H17A C17 H17B 108.5 . . ?
N1 C2 N2 105.38(14) . . ?
N1 C2 C6 113.74(14) . . ?
N2 C2 C6 105.74(14) . . ?
N1 C2 H2 110.6 . . ?
N2 C2 H2 110.6 . . ?
C6 C2 H2 110.6 . . ?
C13 C14 C15 119.81(19) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C8 C5 C6 113.45(15) . . ?
C8 C5 C4 114.67(15) . . ?
C6 C5 C4 101.59(14) . . ?
C8 C5 H5 108.9 . . ?
C6 C5 H5 108.9 . . ?
C4 C5 H5 108.9 . . ?
N2 C4 C16 111.25(15) . . ?
N2 C4 C5 104.06(14) . . ?
C16 C4 C5 109.49(14) . . ?
N2 C4 H4 110.6 . . ?
C16 C4 H4 110.6 . . ?
C5 C4 H4 110.6 . . ?
N3 C7 C6 178.5(2) . . ?
C7 C6 C5 112.65(15) . . ?
C7 C6 C2 114.17(15) . . ?
C5 C6 C2 102.83(14) . . ?
C7 C6 H6 109.0 . . ?
C5 C6 H6 109.0 . . ?
C2 C6 H6 109.0 . . ?
C12 C11 C10 120.51(19) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
N1 C9 C10 110.11(15) . . ?
N1 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
N1 C1 C3 101.72(15) . . ?
N1 C1 H1A 111.4 . . ?
C3 C1 H1A 111.4 . . ?
N1 C1 H1B 111.4 . . ?
C3 C1 H1B 111.4 . . ?
H1A C1 H1B 109.3 . . ?
C12 C13 C14 119.85(19) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.993
_diffrn_reflns_theta_full              25.03
_diffrn_measured_fraction_theta_full   0.993
_refine_diff_density_max    0.162
_refine_diff_density_min   -0.259
_refine_diff_density_rms    0.048
