 
data_2009src0518
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C16 H16 N6 O3'
_chemical_formula_weight          340.35
 
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'
 '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/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                    11.5481(4)
_cell_length_b                    8.4612(4)
_cell_length_c                    16.5109(8)
_cell_angle_alpha                 90.00
_cell_angle_beta                  98.323(3)
_cell_angle_gamma                 90.00
_cell_volume                      1596.30(12)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     11243
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.19
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.11
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.416
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              712
_exptl_absorpt_coefficient_mu     0.103
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9808
_exptl_absorpt_correction_T_max   0.9888
_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    'graphite'
_diffrn_measurement_device_type   
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '9.091'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             19184
_diffrn_reflns_av_R_equivalents   0.0840
_diffrn_reflns_av_sigmaI/netI     0.0789
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          3.14
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3644
_reflns_number_gt                 2346
_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)+(0.0765P)²+0.5476P] 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        0.014(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3644
_refine_ls_number_parameters      234
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1033
_refine_ls_R_factor_gt            0.0607
_refine_ls_wR_factor_ref          0.1698
_refine_ls_wR_factor_gt           0.1434
_refine_ls_goodness_of_fit_ref    1.031
_refine_ls_restrained_S_all       1.031
_refine_ls_shift/su_max           0.003
_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
C1 C 1.0249(2) 0.2073(3) -0.01964(16) 0.0387(6) Uani 1 1 d . . .
H1A H 0.9679 0.1469 -0.0572 0.058 Uiso 1 1 calc R . .
H1B H 1.0933 0.1410 -0.0015 0.058 Uiso 1 1 calc R . .
H1C H 1.0492 0.3009 -0.0478 0.058 Uiso 1 1 calc R . .
C3 C 0.87737(19) 0.3533(3) 0.03563(15) 0.0283(5) Uani 1 1 d . . .
C4 C 0.8268(2) 0.4052(3) -0.04175(15) 0.0286(5) Uani 1 1 d . . .
H4 H 0.8576 0.3725 -0.0894 0.034 Uiso 1 1 calc R . .
C5 C 0.73037(19) 0.5056(3) -0.04798(14) 0.0278(5) Uani 1 1 d . . .
H5 H 0.6955 0.5412 -0.1005 0.033 Uiso 1 1 calc R . .
C6 C 0.68409(19) 0.5547(3) 0.02089(14) 0.0248(5) Uani 1 1 d . . .
C7 C 0.73555(19) 0.5006(3) 0.09823(14) 0.0265(5) Uani 1 1 d . . .
H7 H 0.7042 0.5318 0.1459 0.032 Uiso 1 1 calc R . .
C8 C 0.83165(18) 0.4021(3) 0.10489(14) 0.0281(5) Uani 1 1 d . . .
H8 H 0.8670 0.3673 0.1574 0.034 Uiso 1 1 calc R . .
C9 C 0.58331(18) 0.6603(3) 0.01395(13) 0.0238(5) Uani 1 1 d . . .
C11 C 0.43947(18) 0.8186(3) -0.01955(13) 0.0247(5) Uani 1 1 d . . .
C12 C 0.45322(18) 0.8035(3) 0.06319(14) 0.0238(5) Uani 1 1 d . . .
C14 C 0.35959(18) 0.9104(3) -0.07715(14) 0.0257(5) Uani 1 1 d . . .
C20 C 0.3229(2) 0.9826(3) 0.12854(15) 0.0323(6) Uani 1 1 d . . .
H20 H 0.2878 1.0403 0.0820 0.039 Uiso 1 1 calc R . .
C21 C 0.3033(2) 1.0043(3) 0.20664(16) 0.0348(6) Uani 1 1 d . . .
H21 H 0.2518 1.0801 0.2245 0.042 Uiso 1 1 calc R . .
C22 C 0.3731(2) 0.8943(3) 0.25733(15) 0.0329(6) Uani 1 1 d . . .
H22 H 0.3761 0.8832 0.3149 0.040 Uiso 1 1 calc R . .
C23 C 0.4343(2) 0.8085(3) 0.20921(14) 0.0308(6) Uani 1 1 d . . .
H23 H 0.4886 0.7270 0.2270 0.037 Uiso 1 1 calc R . .
N10 N 0.52406(15) 0.7255(2) -0.04992(12) 0.0254(5) Uani 1 1 d . . .
N15 N 0.35906(17) 0.9040(2) -0.15818(12) 0.0303(5) Uani 1 1 d D . .
N16 N 0.27519(18) 1.0021(3) -0.19445(13) 0.0351(5) Uani 1 1 d . . .
N17 N 0.22762(18) 1.0654(3) -0.13588(12) 0.0350(5) Uani 1 1 d . . .
N18 N 0.27771(16) 1.0118(2) -0.06144(12) 0.0303(5) Uani 1 1 d . . .
N19 N 0.40375(15) 0.8605(2) 0.12859(11) 0.0256(5) Uani 1 1 d . . .
O2 O 0.97255(14) 0.2557(2) 0.04982(11) 0.0346(4) Uani 1 1 d . . .
O13 O 0.54442(12) 0.70166(18) 0.08582(9) 0.0255(4) Uani 1 1 d . . .
H15 H 0.397(2) 0.843(3) -0.1912(15) 0.039(8) Uiso 1 1 d D . .
O31 O 0.05012(14) 1.2492(2) -0.22467(10) 0.0361(5) Uani 1 1 d . . .
H31 H 0.1086 1.2152 -0.1933 0.054 Uiso 1 1 calc R . .
C32 C -0.0301(2) 1.1251(4) -0.24489(18) 0.0500(8) Uani 1 1 d . . .
H32A H -0.0295 1.0551 -0.1975 0.075 Uiso 1 1 calc R . .
H32B H -0.0077 1.0650 -0.2910 0.075 Uiso 1 1 calc R . .
H32C H -0.1088 1.1688 -0.2602 0.075 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
C1 O2 1.431(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 O2 1.368(3) . ?
C3 C8 1.390(3) . ?
C3 C4 1.397(3) . ?
C4 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.405(3) . ?
C6 C9 1.459(3) . ?
C7 C8 1.379(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 N10 1.294(3) . ?
C9 O13 1.373(3) . ?
C11 C12 1.358(3) . ?
C11 N10 1.403(3) . ?
C11 C14 1.451(3) . ?
C12 O13 1.370(3) . ?
C12 N19 1.380(3) . ?
C14 N18 1.330(3) . ?
C14 N15 1.338(3) . ?
C20 C21 1.354(3) . ?
C20 N19 1.392(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.422(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.349(3) . ?
C22 H22 0.9500 . ?
C23 N19 1.398(3) . ?
C23 H23 0.9500 . ?
N15 N16 1.348(3) . ?
N15 H15 0.911(17) . ?
N16 N17 1.295(3) . ?
N17 N18 1.358(3) . ?
O31 C32 1.408(3) . ?
O31 H31 0.8400 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C3 C8 115.5(2) . . ?
O2 C3 C4 124.5(2) . . ?
C8 C3 C4 120.0(2) . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.0(2) . . ?
C5 C6 C9 121.1(2) . . ?
C7 C6 C9 119.9(2) . . ?
C8 C7 C6 119.9(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C3 120.7(2) . . ?
C7 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
N10 C9 O13 113.28(19) . . ?
N10 C9 C6 130.3(2) . . ?
O13 C9 C6 116.42(18) . . ?
C12 C11 N10 108.69(19) . . ?
C12 C11 C14 132.9(2) . . ?
N10 C11 C14 118.4(2) . . ?
C11 C12 O13 107.87(19) . . ?
C11 C12 N19 138.8(2) . . ?
O13 C12 N19 113.30(18) . . ?
N18 C14 N15 108.7(2) . . ?
N18 C14 C11 128.3(2) . . ?
N15 C14 C11 123.0(2) . . ?
C21 C20 N19 107.7(2) . . ?
C21 C20 H20 126.1 . . ?
N19 C20 H20 126.1 . . ?
C20 C21 C22 108.3(2) . . ?
C20 C21 H21 125.9 . . ?
C22 C21 H21 125.9 . . ?
C23 C22 C21 107.8(2) . . ?
C23 C22 H22 126.1 . . ?
C21 C22 H22 126.1 . . ?
C22 C23 N19 108.1(2) . . ?
C22 C23 H23 126.0 . . ?
N19 C23 H23 126.0 . . ?
C9 N10 C11 105.14(19) . . ?
C14 N15 N16 108.6(2) . . ?
C14 N15 H15 133.6(17) . . ?
N16 N15 H15 117.6(17) . . ?
N17 N16 N15 106.15(19) . . ?
N16 N17 N18 111.48(19) . . ?
C14 N18 N17 105.12(19) . . ?
C12 N19 C20 127.78(19) . . ?
C12 N19 C23 124.01(19) . . ?
C20 N19 C23 108.10(19) . . ?
C3 O2 C1 117.22(19) . . ?
C12 O13 C9 105.01(16) . . ?
C32 O31 H31 109.5 . . ?
O31 C32 H32A 109.5 . . ?
O31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
N15 H15 O31  0.911(17) 1.781(18) 2.673(3) 166(3) 2_544
O31 H31 N17  0.84 2.00 2.810(3) 160.6 .
O31 H31 N16  0.84 2.64 3.316(3) 138.7 .
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.286
_refine_diff_density_min   -0.282
_refine_diff_density_rms    0.073
