 
data_2009src0062p21c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H17 N5 O'
_chemical_formula_weight          271.33
 
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/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                    13.5783(7)
_cell_length_b                    8.2142(4)
_cell_length_c                    12.6554(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  103.051(3)
_cell_angle_gamma                 90.00
_cell_volume                      1375.06(11)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     8933
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        lath
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.15
_exptl_crystal_size_mid           0.04
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.311
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              576
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9869
_exptl_absorpt_correction_T_max   0.9991
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    '10cm confocal mirrors'
_diffrn_measurement_device_type   
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             10935
_diffrn_reflns_av_R_equivalents   0.1054
_diffrn_reflns_av_sigmaI/netI     0.0847
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        16
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          2.92
_diffrn_reflns_theta_max          24.99
_reflns_number_total              2411
_reflns_number_gt                 1544
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'  
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_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 > 2σ(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)+(0.0081P)²+3.4289P] 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          2411
_refine_ls_number_parameters      183
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1455
_refine_ls_R_factor_gt            0.0868
_refine_ls_wR_factor_ref          0.1845
_refine_ls_wR_factor_gt           0.1533
_refine_ls_goodness_of_fit_ref    1.142
_refine_ls_restrained_S_all       1.142
_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
C8 C 0.4441(3) 0.4344(5) 0.3124(4) 0.0363(11) Uani 1 1 d . . .
H8A H 0.4753 0.4865 0.2574 0.044 Uiso 1 1 calc R . .
H8B H 0.4117 0.5206 0.3475 0.044 Uiso 1 1 calc R . .
C9 C 0.3652(3) 0.3141(5) 0.2576(3) 0.0318(10) Uani 1 1 d . . .
H9A H 0.3097 0.3723 0.2077 0.038 Uiso 1 1 calc R . .
H9B H 0.3955 0.2361 0.2144 0.038 Uiso 1 1 calc R . .
C11 C 0.4028(3) 0.1453(5) 0.4217(3) 0.0302(10) Uani 1 1 d . . .
H11A H 0.4358 0.0592 0.3872 0.036 Uiso 1 1 calc R . .
H11B H 0.3717 0.0936 0.4769 0.036 Uiso 1 1 calc R . .
C12 C 0.4803(3) 0.2682(5) 0.4752(3) 0.0344(11) Uani 1 1 d . . .
H12A H 0.4485 0.3479 0.5158 0.041 Uiso 1 1 calc R . .
H12B H 0.5351 0.2123 0.5275 0.041 Uiso 1 1 calc R . .
N10 N 0.3245(2) 0.2252(4) 0.3395(3) 0.0284(8) Uani 1 1 d . . .
C2 C 0.7596(3) 0.1651(5) 0.4175(4) 0.0359(11) Uani 1 1 d . . .
H2 H 0.8041 0.0948 0.4656 0.043 Uiso 1 1 calc R . .
C3 C 0.7890(3) 0.2217(6) 0.3275(4) 0.0395(11) Uani 1 1 d . . .
H3 H 0.8520 0.1921 0.3123 0.047 Uiso 1 1 calc R . .
C4 C 0.7221(3) 0.3239(6) 0.2598(4) 0.0409(12) Uani 1 1 d . . .
H4 H 0.7403 0.3649 0.1966 0.049 Uiso 1 1 calc R . .
C6 C 0.6122(3) 0.3060(5) 0.3700(3) 0.0291(10) Uani 1 1 d . . .
C13 C 0.2286(3) 0.2323(5) 0.3519(3) 0.0265(9) Uani 1 1 d . . .
C14 C 0.1502(3) 0.3030(5) 0.2632(3) 0.0256(9) Uani 1 1 d . . .
C15 C 0.1318(3) 0.2798(5) 0.1529(3) 0.0316(10) Uani 1 1 d . . .
H15 H 0.1732 0.2210 0.1149 0.038 Uiso 1 1 calc R . .
C16 C 0.0406(3) 0.3588(5) 0.1065(4) 0.0364(11) Uani 1 1 d . . .
H16 H 0.0086 0.3628 0.0316 0.044 Uiso 1 1 calc R . .
C17 C 0.0067(3) 0.4286(6) 0.1890(4) 0.0382(11) Uani 1 1 d . . .
H17 H -0.0530 0.4921 0.1812 0.046 Uiso 1 1 calc R . .
C19 C 0.0631(4) 0.4566(7) 0.3901(4) 0.0544(15) Uani 1 1 d . . .
H19A H 0.0059 0.5322 0.3799 0.082 Uiso 1 1 calc R . .
H19B H 0.1255 0.5140 0.4243 0.082 Uiso 1 1 calc R . .
H19C H 0.0520 0.3663 0.4367 0.082 Uiso 1 1 calc R . .
N1 N 0.6715(3) 0.2043(4) 0.4408(3) 0.0333(9) Uani 1 1 d . . .
N5 N 0.6336(3) 0.3676(5) 0.2791(3) 0.0372(9) Uani 1 1 d . . .
N7 N 0.5229(3) 0.3535(4) 0.3944(3) 0.0349(9) Uani 1 1 d . . .
N18 N 0.0721(3) 0.3928(4) 0.2847(3) 0.0348(9) Uani 1 1 d . . .
O20 O 0.2038(2) 0.1752(4) 0.4328(2) 0.0388(8) Uani 1 1 d . . .
 
 
_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
C8 N7 1.469(5) . ?
C8 C9 1.507(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N10 1.474(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 N10 1.464(5) . ?
C11 C12 1.505(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N7 1.462(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
N10 C13 1.347(5) . ?
C2 N1 1.334(5) . ?
C2 C3 1.371(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(6) . ?
C3 H3 0.9500 . ?
C4 N5 1.329(6) . ?
C4 H4 0.9500 . ?
C6 N5 1.346(5) . ?
C6 N1 1.350(5) . ?
C6 N7 1.374(5) . ?
C13 O20 1.240(5) . ?
C13 C14 1.480(6) . ?
C14 N18 1.368(5) . ?
C14 C15 1.375(5) . ?
C15 C16 1.404(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.359(6) . ?
C16 H16 0.9500 . ?
C17 N18 1.362(5) . ?
C17 H17 0.9500 . ?
C19 N18 1.464(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
N7 C8 C9 110.9(4) . . ?
N7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N7 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
N10 C9 C8 110.0(3) . . ?
N10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
N10 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N10 C11 C12 110.0(3) . . ?
N10 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
N10 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N7 C12 C11 110.7(3) . . ?
N7 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
N7 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C13 N10 C11 120.2(3) . . ?
C13 N10 C9 125.9(3) . . ?
C11 N10 C9 113.2(3) . . ?
N1 C2 C3 123.0(4) . . ?
N1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
C2 C3 C4 116.6(4) . . ?
C2 C3 H3 121.7 . . ?
C4 C3 H3 121.7 . . ?
N5 C4 C3 123.0(4) . . ?
N5 C4 H4 118.5 . . ?
C3 C4 H4 118.5 . . ?
N5 C6 N1 126.0(4) . . ?
N5 C6 N7 117.1(4) . . ?
N1 C6 N7 116.9(4) . . ?
O20 C13 N10 121.9(4) . . ?
O20 C13 C14 119.5(4) . . ?
N10 C13 C14 118.5(3) . . ?
N18 C14 C15 107.7(4) . . ?
N18 C14 C13 121.2(4) . . ?
C15 C14 C13 130.6(4) . . ?
C14 C15 C16 107.6(4) . . ?
C14 C15 H15 126.2 . . ?
C16 C15 H15 126.2 . . ?
C17 C16 C15 107.1(4) . . ?
C17 C16 H16 126.5 . . ?
C15 C16 H16 126.5 . . ?
C16 C17 N18 109.0(4) . . ?
C16 C17 H17 125.5 . . ?
N18 C17 H17 125.5 . . ?
N18 C19 H19A 109.5 . . ?
N18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 N1 C6 115.7(4) . . ?
C4 N5 C6 115.7(4) . . ?
C6 N7 C12 122.0(3) . . ?
C6 N7 C8 120.6(4) . . ?
C12 N7 C8 111.8(3) . . ?
C17 N18 C14 108.6(4) . . ?
C17 N18 C19 124.1(4) . . ?
C14 N18 C19 127.0(4) . . ?
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              24.99
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.279
_refine_diff_density_min   -0.305
_refine_diff_density_rms    0.065
