 
data_2009src0459
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C10 H13 N3 O'
_chemical_formula_weight          191.23
 
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            triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    5.4433(2)
_cell_length_b                    6.1440(3)
_cell_length_c                    15.5205(7)
_cell_angle_alpha                 87.696(3)
_cell_angle_beta                  84.420(3)
_cell_angle_gamma                 70.454(2)
_cell_volume                      486.82(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     9562
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.09
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.305
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              204
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9921
_exptl_absorpt_correction_T_max   0.9965
_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             8859
_diffrn_reflns_av_R_equivalents   0.0580
_diffrn_reflns_av_sigmaI/netI     0.0485
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          3.52
_diffrn_reflns_theta_max          27.47
_reflns_number_total              2205
_reflns_number_gt                 1737
_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)+(0.0257P)²+0.4910P] 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      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2205
_refine_ls_number_parameters      135
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0797
_refine_ls_R_factor_gt            0.0591
_refine_ls_wR_factor_ref          0.1309
_refine_ls_wR_factor_gt           0.1184
_refine_ls_goodness_of_fit_ref    1.083
_refine_ls_restrained_S_all       1.082
_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
C1 C 0.4825(4) 0.4899(3) 0.26341(12) 0.0217(4) Uani 1 1 d . . .
H1 H 0.3240 0.4798 0.2385 0.026 Uiso 1 1 calc R . .
C2 C 0.4966(4) 0.3718(4) 0.35281(13) 0.0275(5) Uani 1 1 d . . .
H2A H 0.5147 0.2073 0.3463 0.033 Uiso 1 1 calc R . .
H2B H 0.6522 0.3783 0.3793 0.033 Uiso 1 1 calc R . .
C3 C 0.2492(4) 0.4918(4) 0.41174(15) 0.0335(5) Uani 1 1 d . . .
H3A H 0.0966 0.4691 0.3884 0.040 Uiso 1 1 calc R . .
H3B H 0.2664 0.4203 0.4701 0.040 Uiso 1 1 calc R . .
C4 C 0.2018(5) 0.7495(4) 0.41884(15) 0.0366(6) Uani 1 1 d . . .
H4A H 0.0324 0.8234 0.4529 0.044 Uiso 1 1 calc R . .
H4B H 0.3416 0.7726 0.4499 0.044 Uiso 1 1 calc R . .
C5 C 0.1979(4) 0.8641(4) 0.32996(15) 0.0329(5) Uani 1 1 d . . .
H5A H 0.1800 1.0284 0.3367 0.040 Uiso 1 1 calc R . .
H5B H 0.0442 0.8586 0.3020 0.040 Uiso 1 1 calc R . .
C6 C 0.4471(4) 0.7451(3) 0.27194(14) 0.0267(5) Uani 1 1 d . . .
H6A H 0.4354 0.8194 0.2140 0.032 Uiso 1 1 calc R . .
H6B H 0.6001 0.7614 0.2972 0.032 Uiso 1 1 calc R . .
C7 C 0.7139(4) 0.3701(3) 0.20305(12) 0.0212(4) Uani 1 1 d . . .
C9 C 0.9669(4) 0.0704(3) 0.12838(12) 0.0206(4) Uani 1 1 d . . .
C10 C 1.0552(4) 0.2546(3) 0.11390(12) 0.0211(4) Uani 1 1 d . . .
C13 C 1.2735(4) 0.2652(3) 0.05867(13) 0.0227(4) Uani 1 1 d . . .
N11 N 0.8879(3) 0.4445(3) 0.16281(11) 0.0222(4) Uani 1 1 d . . .
N12 N 1.0452(3) -0.1455(3) 0.10050(12) 0.0264(4) Uani 1 1 d D . .
N14 N 1.4526(3) 0.2695(3) 0.01375(12) 0.0303(4) Uani 1 1 d . . .
O8 O 0.7498(3) 0.1410(2) 0.18575(9) 0.0224(3) Uani 1 1 d . . .
H12B H 0.968(4) -0.242(3) 0.1216(14) 0.025(6) Uiso 1 1 d D . .
H12A H 1.188(4) -0.196(4) 0.0643(14) 0.037(7) Uiso 1 1 d D . .
 
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
C1 0.0177(9) 0.0235(10) 0.0237(10) -0.0032(8) 0.0017(7) -0.0074(8)
C2 0.0239(10) 0.0285(11) 0.0275(11) -0.0016(9) 0.0038(8) -0.0069(9)
C3 0.0280(11) 0.0389(13) 0.0286(12) -0.0028(9) 0.0089(9) -0.0073(10)
C4 0.0303(12) 0.0381(13) 0.0357(13) -0.0139(10) 0.0061(10) -0.0047(10)
C5 0.0250(11) 0.0258(11) 0.0446(13) -0.0079(10) 0.0028(9) -0.0048(9)
C6 0.0228(10) 0.0216(10) 0.0347(12) -0.0016(8) 0.0008(9) -0.0069(8)
C7 0.0210(9) 0.0198(9) 0.0230(10) -0.0021(8) -0.0010(8) -0.0071(8)
C9 0.0199(9) 0.0222(9) 0.0196(9) -0.0004(7) 0.0019(7) -0.0076(8)
C10 0.0218(9) 0.0211(10) 0.0205(10) -0.0007(7) 0.0021(7) -0.0082(8)
C13 0.0238(10) 0.0194(10) 0.0255(10) -0.0008(8) 0.0006(8) -0.0089(8)
N11 0.0200(8) 0.0224(9) 0.0239(9) -0.0026(7) 0.0027(6) -0.0075(7)
N12 0.0277(9) 0.0203(9) 0.0319(10) -0.0053(7) 0.0101(8) -0.0120(7)
N14 0.0288(9) 0.0247(9) 0.0380(11) -0.0033(8) 0.0085(8) -0.0125(8)
O8 0.0217(7) 0.0207(7) 0.0255(7) -0.0033(5) 0.0056(6) -0.0098(5)
 
_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 C7 1.487(3) . ?
C1 C6 1.524(3) . ?
C1 C2 1.536(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.531(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.524(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.522(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.529(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N11 1.284(2) . ?
C7 O8 1.388(2) . ?
C9 N12 1.327(3) . ?
C9 O8 1.364(2) . ?
C9 C10 1.373(3) . ?
C10 N11 1.411(2) . ?
C10 C13 1.414(3) . ?
C13 N14 1.149(2) . ?
N12 H12B 0.872(16) . ?
N12 H12A 0.887(16) . ?
 
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
C7 C1 C6 111.78(16) . . ?
C7 C1 C2 111.70(16) . . ?
C6 C1 C2 110.58(16) . . ?
C7 C1 H1 107.5 . . ?
C6 C1 H1 107.5 . . ?
C2 C1 H1 107.5 . . ?
C3 C2 C1 110.29(17) . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 111.71(18) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 111.40(18) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 111.65(18) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C1 C6 C5 109.95(16) . . ?
C1 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
C1 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N11 C7 O8 113.56(16) . . ?
N11 C7 C1 130.52(18) . . ?
O8 C7 C1 115.92(15) . . ?
N12 C9 O8 117.89(16) . . ?
N12 C9 C10 135.01(18) . . ?
O8 C9 C10 107.10(16) . . ?
C9 C10 N11 109.11(16) . . ?
C9 C10 C13 127.88(18) . . ?
N11 C10 C13 123.00(17) . . ?
N14 C13 C10 178.7(2) . . ?
C7 N11 C10 104.81(16) . . ?
C9 N12 H12B 120.7(15) . . ?
C9 N12 H12A 119.5(16) . . ?
H12B N12 H12A 119(2) . . ?
C9 O8 C7 105.42(14) . . ?
 
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
N12 H12B N11  0.872(16) 2.172(17) 3.017(2) 163(2) 1_545
N12 H12A N14  0.887(16) 2.118(17) 2.995(2) 170(2) 2_855
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              27.47
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.293
_refine_diff_density_min   -0.280
_refine_diff_density_rms    0.055
