 
data_2009src0462
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C15 H11 N3 O2'
_chemical_formula_weight          265.27
 
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                    4.95560(10)
_cell_length_b                    15.8959(4)
_cell_length_c                    15.8659(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  92.257(2)
_cell_angle_gamma                 90.00
_cell_volume                      1248.85(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     13380
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.67
_exptl_crystal_size_mid           0.07
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.411
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              552
_exptl_absorpt_coefficient_mu     0.097
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9378
_exptl_absorpt_correction_T_max   0.9961
_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             14753
_diffrn_reflns_av_R_equivalents   0.0588
_diffrn_reflns_av_sigmaI/netI     0.0500
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -20
_diffrn_reflns_limit_k_max        20
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          3.63
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2865
_reflns_number_gt                 2147
_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)+(0.0211P)²+1.5761P] 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          2865
_refine_ls_number_parameters      182
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0895
_refine_ls_R_factor_gt            0.0617
_refine_ls_wR_factor_ref          0.1322
_refine_ls_wR_factor_gt           0.1159
_refine_ls_goodness_of_fit_ref    1.080
_refine_ls_restrained_S_all       1.080
_refine_ls_shift/su_max           0.002
_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 -0.2315(4) 0.09373(13) 0.36113(13) 0.0217(4) Uani 1 1 d . . .
C2 C -0.2740(4) 0.16865(14) 0.31604(14) 0.0238(5) Uani 1 1 d . . .
H2 H -0.1742 0.1799 0.2674 0.029 Uiso 1 1 calc R . .
C3 C -0.4615(4) 0.22592(13) 0.34260(14) 0.0243(5) Uani 1 1 d . . .
H3 H -0.4916 0.2764 0.3116 0.029 Uiso 1 1 calc R . .
C4 C -0.6071(4) 0.21060(13) 0.41419(14) 0.0224(5) Uani 1 1 d . . .
C5 C -0.5688(4) 0.13576(13) 0.45937(14) 0.0238(5) Uani 1 1 d . . .
H5 H -0.6707 0.1242 0.5075 0.029 Uiso 1 1 calc R . .
C6 C -0.3786(4) 0.07867(13) 0.43239(14) 0.0230(5) Uani 1 1 d . . .
H6 H -0.3484 0.0281 0.4633 0.028 Uiso 1 1 calc R . .
C7 C -0.0389(4) 0.03077(13) 0.33524(13) 0.0214(4) Uani 1 1 d . . .
C9 C 0.2759(4) -0.01785(13) 0.25765(13) 0.0226(5) Uani 1 1 d . . .
C10 C 0.2095(4) -0.07666(14) 0.31580(13) 0.0236(5) Uani 1 1 d . . .
C13 C 0.5017(5) 0.05593(15) 0.14355(14) 0.0282(5) Uani 1 1 d . . .
H13 H 0.4117 0.1086 0.1456 0.034 Uiso 1 1 calc R . .
C14 C 0.6998(5) 0.03460(16) 0.09116(15) 0.0323(5) Uani 1 1 d . . .
H14 H 0.7737 0.0701 0.0498 0.039 Uiso 1 1 calc R . .
C15 C 0.7783(5) -0.04956(15) 0.10851(14) 0.0298(5) Uani 1 1 d . . .
H15 H 0.9141 -0.0802 0.0811 0.036 Uiso 1 1 calc R . .
C16 C 0.6255(5) -0.07858(15) 0.17120(15) 0.0287(5) Uani 1 1 d . . .
H16 H 0.6338 -0.1333 0.1953 0.034 Uiso 1 1 calc R . .
C17 C 0.3126(5) -0.15968(15) 0.32862(14) 0.0262(5) Uani 1 1 d . . .
C20 C -0.9437(5) 0.25832(15) 0.50710(15) 0.0287(5) Uani 1 1 d . . .
H20A H -1.0406 0.2049 0.4996 0.043 Uiso 1 1 calc R . .
H20B H -1.0741 0.3043 0.5118 0.043 Uiso 1 1 calc R . .
H20C H -0.8280 0.2558 0.5586 0.043 Uiso 1 1 calc R . .
N11 N 0.0047(4) -0.04401(11) 0.36501(11) 0.0237(4) Uani 1 1 d . . .
N12 N 0.4545(4) -0.01399(11) 0.19391(11) 0.0236(4) Uani 1 1 d . . .
N18 N 0.3925(4) -0.22688(13) 0.33870(13) 0.0340(5) Uani 1 1 d . . .
O8 O 0.1220(3) 0.05098(9) 0.26886(9) 0.0218(3) Uani 1 1 d . . .
O19 O -0.7807(3) 0.27293(9) 0.43602(10) 0.0284(4) 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
C1 C6 1.390(3) . ?
C1 C2 1.401(3) . ?
C1 C7 1.453(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 O19 1.366(3) . ?
C4 C5 1.398(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N11 1.294(3) . ?
C7 O8 1.384(2) . ?
C9 O8 1.350(3) . ?
C9 C10 1.363(3) . ?
C9 N12 1.371(3) . ?
C10 N11 1.404(3) . ?
C10 C17 1.427(3) . ?
C13 C14 1.354(3) . ?
C13 N12 1.394(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.417(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.355(3) . ?
C15 H15 0.9500 . ?
C16 N12 1.388(3) . ?
C16 H16 0.9500 . ?
C17 N18 1.148(3) . ?
C20 O19 1.432(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C6 C1 C2 119.2(2) . . ?
C6 C1 C7 118.86(19) . . ?
C2 C1 C7 121.90(19) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
O19 C4 C3 115.61(19) . . ?
O19 C4 C5 124.2(2) . . ?
C3 C4 C5 120.2(2) . . ?
C6 C5 C4 118.6(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 121.5(2) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
N11 C7 O8 113.44(18) . . ?
N11 C7 C1 129.2(2) . . ?
O8 C7 C1 117.38(18) . . ?
O8 C9 C10 108.30(19) . . ?
O8 C9 N12 116.45(19) . . ?
C10 C9 N12 135.3(2) . . ?
C9 C10 N11 108.79(19) . . ?
C9 C10 C17 129.5(2) . . ?
N11 C10 C17 121.7(2) . . ?
C14 C13 N12 107.1(2) . . ?
C14 C13 H13 126.4 . . ?
N12 C13 H13 126.4 . . ?
C13 C14 C15 108.5(2) . . ?
C13 C14 H14 125.8 . . ?
C15 C14 H14 125.8 . . ?
C16 C15 C14 107.9(2) . . ?
C16 C15 H15 126.1 . . ?
C14 C15 H15 126.1 . . ?
C15 C16 N12 107.7(2) . . ?
C15 C16 H16 126.2 . . ?
N12 C16 H16 126.2 . . ?
N18 C17 C10 179.2(3) . . ?
O19 C20 H20A 109.5 . . ?
O19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 N11 C10 104.52(18) . . ?
C9 N12 C16 125.22(19) . . ?
C9 N12 C13 125.89(19) . . ?
C16 N12 C13 108.85(18) . . ?
C9 O8 C7 104.94(16) . . ?
C4 O19 C20 117.56(17) . . ?
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.243
_refine_diff_density_min   -0.242
_refine_diff_density_rms    0.059
