data_s93
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Prof. R. C. F. Jones
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H19 N5 O2'
_chemical_formula_weight          349.39
 
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)/c
_symmetry_space_group_name_hall   '-P 2ybc'
 
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                    15.0361(5)
_cell_length_b                    11.7861(3)
_cell_length_c                    10.4725(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  100.5280(10)
_cell_angle_gamma                 90.00
_cell_volume                      1824.66(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4285
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.32
_exptl_crystal_size_mid           0.22
_exptl_crystal_size_min           0.22
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.272
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              736
_exptl_absorpt_coefficient_mu     0.086
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9729
_exptl_absorpt_correction_T_max   0.9813
_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             20550
_diffrn_reflns_av_R_equivalents   0.0758
_diffrn_reflns_av_sigmaI/netI     0.0691
_diffrn_reflns_limit_h_min        -19
_diffrn_reflns_limit_h_max        19
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.25
_diffrn_reflns_theta_max          27.51
_reflns_number_total              4169
_reflns_number_gt                 2593
_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)+(0.0632P)²+0.0344P] where P=(Fo²+2Fc²)/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        0.0064(15)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4169
_refine_ls_number_parameters      312
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1001
_refine_ls_R_factor_gt            0.0487
_refine_ls_wR_factor_ref          0.1225
_refine_ls_wR_factor_gt           0.1048
_refine_ls_goodness_of_fit_ref    1.006
_refine_ls_restrained_S_all       1.006
_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_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.01377(8) 0.37543(10) 0.29541(10) 0.0253(3) Uani 1 1 d . . .
O2 O -0.11758(8) 0.08552(11) 0.04389(12) 0.0337(3) Uani 1 1 d . . .
N1 N 0.30852(9) 0.31564(12) 0.28534(14) 0.0257(3) Uani 1 1 d . . .
N2 N 0.16589(9) 0.23002(12) 0.27367(13) 0.0215(3) Uani 1 1 d . . .
N3 N -0.01577(11) 0.39656(13) -0.10145(14) 0.0298(4) Uani 1 1 d . . .
N4 N 0.28076(12) 0.52773(15) 0.04752(17) 0.0418(4) Uani 1 1 d . . .
N5 N -0.07098(9) 0.24361(12) 0.16446(13) 0.0226(3) Uani 1 1 d . . .
C1 C 0.32058(12) 0.19605(16) 0.32453(19) 0.0301(4) Uani 1 1 d . . .
C2 C 0.21352(11) 0.34127(14) 0.28360(16) 0.0218(4) Uani 1 1 d . . .
C3 C 0.23417(12) 0.14358(16) 0.25345(19) 0.0277(4) Uani 1 1 d . . .
C4 C 0.08610(11) 0.23838(14) 0.16955(15) 0.0198(4) Uani 1 1 d . . .
C5 C 0.11849(11) 0.32099(14) 0.07079(15) 0.0215(4) Uani 1 1 d . . .
C6 C 0.16981(11) 0.41187(14) 0.16126(16) 0.0219(4) Uani 1 1 d . . .
C7 C 0.04469(12) 0.36453(14) -0.02734(16) 0.0227(4) Uani 1 1 d . . .
C8 C 0.23360(12) 0.47573(15) 0.09995(17) 0.0282(4) Uani 1 1 d . . .
C9 C 0.36836(12) 0.39482(17) 0.3695(2) 0.0316(4) Uani 1 1 d . . .
C10 C 0.46635(12) 0.37981(17) 0.3611(2) 0.0371(5) Uani 1 1 d . . .
C11 C 0.52648(16) 0.3379(2) 0.4679(3) 0.0584(7) Uani 1 1 d . . .
C12 C 0.61724(19) 0.3270(3) 0.4638(4) 0.0828(10) Uani 1 1 d . . .
C13 C 0.64854(19) 0.3577(3) 0.3547(4) 0.0830(11) Uani 1 1 d . . .
C14 C 0.5912(2) 0.3980(3) 0.2474(4) 0.0745(9) Uani 1 1 d . . .
C15 C 0.49783(16) 0.4095(2) 0.2504(3) 0.0533(6) Uani 1 1 d . . .
C16 C 0.00787(11) 0.29591(14) 0.22102(15) 0.0203(4) Uani 1 1 d . . .
C17 C -0.05687(12) 0.14524(14) 0.09808(15) 0.0238(4) Uani 1 1 d . . .
C18 C 0.04404(11) 0.12803(15) 0.11137(17) 0.0224(4) Uani 1 1 d . . .
C19 C -0.15912(13) 0.27736(19) 0.1912(2) 0.0324(5) Uani 1 1 d . . .
H1A H 0.3274(13) 0.1861(17) 0.424(2) 0.035(5) Uiso 1 1 d . . .
H1B H 0.3745(14) 0.1616(17) 0.3009(18) 0.033(5) Uiso 1 1 d . . .
H2 H 0.2038(11) 0.3846(15) 0.3647(17) 0.019(4) Uiso 1 1 d . . .
H3A H 0.2207(13) 0.0679(17) 0.2888(19) 0.032(5) Uiso 1 1 d . . .
H3B H 0.2342(12) 0.1315(16) 0.158(2) 0.033(5) Uiso 1 1 d . . .
H5 H 0.1587(12) 0.2776(16) 0.0261(18) 0.025(5) Uiso 1 1 d . . .
H6 H 0.1269(11) 0.4637(15) 0.1845(16) 0.017(4) Uiso 1 1 d . . .
H9A H 0.3474(12) 0.4747(17) 0.3419(18) 0.027(5) Uiso 1 1 d . . .
H9B H 0.3587(12) 0.3873(16) 0.459(2) 0.030(5) Uiso 1 1 d . . .
H11 H 0.501(2) 0.324(3) 0.549(4) 0.114(12) Uiso 1 1 d . . .
H12 H 0.665(3) 0.292(4) 0.547(4) 0.142(15) Uiso 1 1 d . . .
H13 H 0.717(2) 0.348(3) 0.363(3) 0.100(10) Uiso 1 1 d . . .
H14 H 0.5961(19) 0.418(2) 0.162(3) 0.073(9) Uiso 1 1 d . . .
H15 H 0.4587(15) 0.4346(18) 0.177(2) 0.040(6) Uiso 1 1 d . . .
H18A H 0.0606(12) 0.1080(15) 0.0299(19) 0.025(5) Uiso 1 1 d . . .
H18B H 0.0596(12) 0.0656(17) 0.170(2) 0.032(5) Uiso 1 1 d . . .
H19A H -0.1944(17) 0.311(2) 0.117(3) 0.065(8) Uiso 1 1 d . . .
H19B H -0.1887(17) 0.210(2) 0.215(3) 0.065(8) Uiso 1 1 d . . .
H19C H -0.1511(17) 0.331(2) 0.265(3) 0.065(7) Uiso 1 1 d . . .
 
 
_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 C16 1.212(2) . ?
O2 C17 1.209(2) . ?
N1 C2 1.457(2) . ?
N1 C1 1.470(2) . ?
N1 C9 1.472(2) . ?
N2 C4 1.470(2) . ?
N2 C2 1.489(2) . ?
N2 C3 1.489(2) . ?
N3 C7 1.146(2) . ?
N4 C8 1.150(2) . ?
N5 C16 1.371(2) . ?
N5 C17 1.388(2) . ?
N5 C19 1.459(2) . ?
C1 C3 1.507(3) . ?
C1 H1A 1.03(2) . ?
C1 H1B 0.98(2) . ?
C2 C6 1.568(2) . ?
C2 H2 1.024(18) . ?
C3 H3A 1.00(2) . ?
C3 H3B 1.01(2) . ?
C4 C18 1.524(2) . ?
C4 C16 1.538(2) . ?
C4 C5 1.562(2) . ?
C5 C7 1.461(2) . ?
C5 C6 1.541(2) . ?
C5 H5 0.974(19) . ?
C6 C8 1.457(3) . ?
C6 H6 0.952(18) . ?
C9 C10 1.502(3) . ?
C9 H9A 1.02(2) . ?
C9 H9B 0.98(2) . ?
C10 C15 1.375(3) . ?
C10 C11 1.394(3) . ?
C11 C12 1.379(4) . ?
C11 H11 1.01(4) . ?
C12 C13 1.362(5) . ?
C12 H12 1.10(4) . ?
C13 C14 1.370(5) . ?
C13 H13 1.03(3) . ?
C14 C15 1.417(4) . ?
C14 H14 0.94(3) . ?
C15 H15 0.93(2) . ?
C17 C18 1.512(2) . ?
C18 H18A 0.961(19) . ?
C18 H18B 0.96(2) . ?
C19 H19A 0.95(3) . ?
C19 H19B 0.97(3) . ?
C19 H19C 0.99(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
C2 N1 C1 105.84(13) . . ?
C2 N1 C9 111.51(14) . . ?
C1 N1 C9 114.20(14) . . ?
C4 N2 C2 108.06(12) . . ?
C4 N2 C3 115.53(13) . . ?
C2 N2 C3 106.09(13) . . ?
C16 N5 C17 113.12(14) . . ?
C16 N5 C19 122.58(15) . . ?
C17 N5 C19 123.45(15) . . ?
N1 C1 C3 101.79(14) . . ?
N1 C1 H1A 112.0(11) . . ?
C3 C1 H1A 111.6(11) . . ?
N1 C1 H1B 113.2(11) . . ?
C3 C1 H1B 112.6(11) . . ?
H1A C1 H1B 105.9(15) . . ?
N1 C2 N2 106.04(13) . . ?
N1 C2 C6 112.58(13) . . ?
N2 C2 C6 106.61(13) . . ?
N1 C2 H2 112.4(9) . . ?
N2 C2 H2 110.9(9) . . ?
C6 C2 H2 108.1(9) . . ?
N2 C3 C1 101.75(15) . . ?
N2 C3 H3A 111.5(11) . . ?
C1 C3 H3A 113.5(11) . . ?
N2 C3 H3B 111.3(11) . . ?
C1 C3 H3B 113.0(11) . . ?
H3A C3 H3B 106.0(16) . . ?
N2 C4 C18 117.54(14) . . ?
N2 C4 C16 110.03(13) . . ?
C18 C4 C16 103.20(13) . . ?
N2 C4 C5 102.82(13) . . ?
C18 C4 C5 115.10(13) . . ?
C16 C4 C5 107.95(13) . . ?
C7 C5 C6 114.77(14) . . ?
C7 C5 C4 113.34(14) . . ?
C6 C5 C4 102.01(12) . . ?
C7 C5 H5 107.7(11) . . ?
C6 C5 H5 112.1(11) . . ?
C4 C5 H5 106.7(11) . . ?
C8 C6 C5 112.59(14) . . ?
C8 C6 C2 115.00(14) . . ?
C5 C6 C2 102.80(13) . . ?
C8 C6 H6 108.2(10) . . ?
C5 C6 H6 108.5(10) . . ?
C2 C6 H6 109.5(10) . . ?
N3 C7 C5 177.07(18) . . ?
N4 C8 C6 176.97(19) . . ?
N1 C9 C10 112.90(16) . . ?
N1 C9 H9A 107.0(10) . . ?
C10 C9 H9A 110.4(10) . . ?
N1 C9 H9B 109.6(11) . . ?
C10 C9 H9B 111.3(11) . . ?
H9A C9 H9B 105.3(15) . . ?
C15 C10 C11 119.6(2) . . ?
C15 C10 C9 120.8(2) . . ?
C11 C10 C9 119.6(2) . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 123(2) . . ?
C10 C11 H11 116(2) . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 119(2) . . ?
C11 C12 H12 121(2) . . ?
C12 C13 C14 121.2(3) . . ?
C12 C13 H13 113.6(19) . . ?
C14 C13 H13 125.2(19) . . ?
C13 C14 C15 119.5(3) . . ?
C13 C14 H14 136.1(18) . . ?
C15 C14 H14 104.3(18) . . ?
C10 C15 C14 119.3(3) . . ?
C10 C15 H15 121.2(14) . . ?
C14 C15 H15 119.5(14) . . ?
O1 C16 N5 125.55(15) . . ?
O1 C16 C4 126.56(15) . . ?
N5 C16 C4 107.86(14) . . ?
O2 C17 N5 123.37(16) . . ?
O2 C17 C18 128.63(16) . . ?
N5 C17 C18 107.98(14) . . ?
C17 C18 C4 104.99(13) . . ?
C17 C18 H18A 111.7(10) . . ?
C4 C18 H18A 114.1(11) . . ?
C17 C18 H18B 106.5(11) . . ?
C4 C18 H18B 111.3(11) . . ?
H18A C18 H18B 108.0(15) . . ?
N5 C19 H19A 110.4(15) . . ?
N5 C19 H19B 107.4(15) . . ?
H19A C19 H19B 110(2) . . ?
N5 C19 H19C 109.9(14) . . ?
H19A C19 H19C 110(2) . . ?
H19B C19 H19C 109(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              27.51
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.257
_refine_diff_density_min   -0.245
_refine_diff_density_rms    0.047
