 
data_2008src0926
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H14 N4 O2'
_chemical_formula_weight          246.27
 
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   0.0000
 '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   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0000
 '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
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    10.9342(2)
_cell_length_b                    8.2762(3)
_cell_length_c                    12.6979(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  92.780(2)
_cell_angle_gamma                 90.00
_cell_volume                      1147.73(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     8599
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        slab
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.44
_exptl_crystal_size_mid           0.17
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.425
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              520
_exptl_absorpt_coefficient_mu     0.101
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9569
_exptl_absorpt_correction_T_max   0.9900
_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             15509
_diffrn_reflns_av_R_equivalents   0.0539
_diffrn_reflns_av_sigmaI/netI     0.0417
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          3.09
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2805
_reflns_number_gt                 2424
_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)+(0.0657P)²+0.0000P] 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      SHELXL
_refine_ls_extinction_coef        0.111(8)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    10(10)
_refine_ls_number_reflns          2805
_refine_ls_number_parameters      326
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0560
_refine_ls_R_factor_gt            0.0454
_refine_ls_wR_factor_ref          0.1083
_refine_ls_wR_factor_gt           0.1030
_refine_ls_goodness_of_fit_ref    1.165
_refine_ls_restrained_S_all       1.165
_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
C2 C 0.0406(2) 0.4465(4) 0.3873(2) 0.0288(6) Uani 1 1 d . . .
H2 H -0.0080 0.3516 0.3910 0.035 Uiso 1 1 calc R . .
C4 C 0.1982(2) 0.6051(3) 0.3693(2) 0.0284(6) Uani 1 1 d . . .
H4 H 0.2779 0.6457 0.3586 0.034 Uiso 1 1 calc R . .
C5 C 0.0961(2) 0.6924(4) 0.3878(2) 0.0323(6) Uani 1 1 d . . .
H5 H 0.0936 0.8069 0.3924 0.039 Uiso 1 1 calc R . .
C6 C 0.2383(2) 0.3074(3) 0.3424(2) 0.0236(6) Uani 1 1 d . . .
H6 H 0.3269 0.3312 0.3589 0.035 Uiso 1 1 calc R . .
C7 C 0.2167(2) 0.2624(3) 0.22572(19) 0.0208(5) Uani 1 1 d . . .
H7 H 0.1963 0.3594 0.1813 0.031 Uiso 1 1 calc R . .
C9 C 0.2901(2) 0.0090(3) 0.1733(2) 0.0270(6) Uani 1 1 d . . .
H9A H 0.3169 -0.0548 0.2362 0.041 Uiso 1 1 calc R . .
H9B H 0.3306 -0.0346 0.1112 0.041 Uiso 1 1 calc R . .
C10 C 0.1515(2) 0.0021(3) 0.15584(19) 0.0222(5) Uani 1 1 d . . .
H10 H 0.1193 -0.1030 0.1819 0.033 Uiso 1 1 calc R . .
C11 C 0.1101(2) 0.1419(3) 0.22509(18) 0.0205(5) Uani 1 1 d . . .
H11 H 0.0321 0.1915 0.1963 0.031 Uiso 1 1 calc R . .
C13 C 0.2005(2) 0.1530(3) 0.3969(2) 0.0273(6) Uani 1 1 d . . .
H13A H 0.2693 0.0752 0.4019 0.041 Uiso 1 1 calc R . .
H13B H 0.1742 0.1764 0.4689 0.041 Uiso 1 1 calc R . .
C15 C -0.0013(3) -0.0174(4) 0.0041(2) 0.0302(6) Uani 1 1 d . . .
H15 H -0.0591 -0.0764 0.0423 0.036 Uiso 1 1 calc R . .
C17 C 0.0837(2) 0.1096(4) -0.1177(2) 0.0284(6) Uani 1 1 d . . .
H17 H 0.0973 0.1580 -0.1840 0.034 Uiso 1 1 calc R . .
C18 C 0.1661(2) 0.1111(3) -0.0328(2) 0.0267(6) Uani 1 1 d . . .
H18 H 0.2451 0.1592 -0.0288 0.032 Uiso 1 1 calc R . .
N1 N -0.0022(2) 0.5933(3) 0.39892(18) 0.0323(6) Uani 1 1 d . . .
N3 N 0.16232(18) 0.4452(3) 0.36934(17) 0.0222(5) Uani 1 1 d . . .
N14 N 0.11030(18) 0.0283(3) 0.04552(16) 0.0227(5) Uani 1 1 d . . .
N16 N -0.0208(2) 0.0286(3) -0.09396(18) 0.0337(6) Uani 1 1 d . . .
O8 O 0.31971(15) 0.1760(2) 0.18831(15) 0.0281(4) Uani 1 1 d . . .
O12 O 0.10049(16) 0.0892(2) 0.33222(13) 0.0259(4) Uani 1 1 d . . .
C22 C 0.4741(2) 0.7340(3) 0.9829(2) 0.0270(6) Uani 1 1 d . . .
H22 H 0.5142 0.7783 0.9248 0.032 Uiso 1 1 calc R . .
C24 C 0.3310(2) 0.6318(3) 1.07789(19) 0.0243(5) Uani 1 1 d . . .
H24 H 0.2553 0.5914 1.1004 0.029 Uiso 1 1 calc R . .
C25 C 0.4385(2) 0.6405(4) 1.1355(2) 0.0286(6) Uani 1 1 d . . .
H25 H 0.4500 0.6072 1.2069 0.034 Uiso 1 1 calc R . .
C26 C 0.2663(2) 0.6931(3) 0.88880(19) 0.0223(5) Uani 1 1 d . . .
H26 H 0.1805 0.7032 0.9120 0.033 Uiso 1 1 calc R . .
C27 C 0.2809(2) 0.5379(3) 0.82410(19) 0.0216(5) Uani 1 1 d . . .
H27 H 0.3076 0.4445 0.8696 0.032 Uiso 1 1 calc R . .
C29 C 0.1893(2) 0.5333(4) 0.6521(2) 0.0311(7) Uani 1 1 d . . .
H29A H 0.1588 0.6422 0.6321 0.047 Uiso 1 1 calc R . .
H29B H 0.1451 0.4523 0.6073 0.047 Uiso 1 1 calc R . .
C30 C 0.3267(2) 0.5217(3) 0.63889(19) 0.0237(5) Uani 1 1 d . . .
H30 H 0.3517 0.5946 0.5809 0.036 Uiso 1 1 calc R . .
C31 C 0.3780(2) 0.5834(3) 0.74578(19) 0.0205(5) Uani 1 1 d . . .
H31 H 0.4591 0.5335 0.7656 0.031 Uiso 1 1 calc R . .
C33 C 0.2933(2) 0.8243(4) 0.8098(2) 0.0269(6) Uani 1 1 d . . .
H33A H 0.2185 0.8526 0.7666 0.040 Uiso 1 1 calc R . .
H33B H 0.3246 0.9227 0.8463 0.040 Uiso 1 1 calc R . .
C35 C 0.4686(2) 0.3166(3) 0.5685(2) 0.0264(6) Uani 1 1 d . . .
H35 H 0.5206 0.3938 0.5380 0.032 Uiso 1 1 calc R . .
C37 C 0.3928(2) 0.0944(4) 0.61898(19) 0.0277(6) Uani 1 1 d . . .
H37 H 0.3808 -0.0179 0.6301 0.033 Uiso 1 1 calc R . .
C38 C 0.3194(2) 0.2129(4) 0.6537(2) 0.0284(6) Uani 1 1 d . . .
H38 H 0.2488 0.1993 0.6935 0.034 Uiso 1 1 calc R . .
N21 N 0.52888(19) 0.7047(3) 1.07585(17) 0.0305(5) Uani 1 1 d . . .
N23 N 0.35379(18) 0.6933(3) 0.98027(15) 0.0215(5) Uani 1 1 d . . .
N34 N 0.36684(18) 0.3564(3) 0.62009(16) 0.0222(5) Uani 1 1 d . . .
N36 N 0.48746(19) 0.1602(3) 0.56510(17) 0.0270(5) Uani 1 1 d . . .
O28 O 0.17120(15) 0.5023(3) 0.76195(13) 0.0287(5) Uani 1 1 d . . .
O32 O 0.38499(17) 0.7564(2) 0.74484(14) 0.0279(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
C2 N1 1.314(4) . ?
C2 N3 1.361(3) . ?
C2 H2 0.9500 . ?
C4 C5 1.359(4) . ?
C4 N3 1.380(4) . ?
C4 H4 0.9500 . ?
C5 N1 1.365(4) . ?
C5 H5 0.9500 . ?
C6 N3 1.462(3) . ?
C6 C13 1.520(4) . ?
C6 C7 1.535(4) . ?
C6 H6 1.0000 . ?
C7 O8 1.435(3) . ?
C7 C11 1.533(3) . ?
C7 H7 1.0000 . ?
C9 O8 1.430(3) . ?
C9 C10 1.522(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N14 1.467(3) . ?
C10 C11 1.535(3) . ?
C10 H10 1.0000 . ?
C11 O12 1.437(3) . ?
C11 H11 1.0000 . ?
C13 O12 1.436(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 N16 1.310(4) . ?
C15 N14 1.359(3) . ?
C15 H15 0.9500 . ?
C17 N16 1.371(4) . ?
C17 C18 1.372(4) . ?
C17 H17 0.9500 . ?
C18 N14 1.374(3) . ?
C18 H18 0.9500 . ?
C22 N21 1.319(3) . ?
C22 N23 1.357(3) . ?
C22 H22 0.9500 . ?
C24 C25 1.356(4) . ?
C24 N23 1.374(3) . ?
C24 H24 0.9500 . ?
C25 N21 1.380(3) . ?
C25 H25 0.9500 . ?
C26 N23 1.469(3) . ?
C26 C33 1.517(4) . ?
C26 C27 1.537(4) . ?
C26 H26 1.0000 . ?
C27 O28 1.434(3) . ?
C27 C31 1.536(3) . ?
C27 H27 1.0000 . ?
C29 O28 1.441(3) . ?
C29 C30 1.523(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 N34 1.459(3) . ?
C30 C31 1.531(4) . ?
C30 H30 1.0000 . ?
C31 O32 1.433(3) . ?
C31 H31 1.0000 . ?
C33 O32 1.443(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C35 N36 1.311(4) . ?
C35 N34 1.359(3) . ?
C35 H35 0.9500 . ?
C37 C38 1.355(4) . ?
C37 N36 1.380(3) . ?
C37 H37 0.9500 . ?
C38 N34 1.372(4) . ?
C38 H38 0.9500 . ?
 
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
N1 C2 N3 112.5(2) . . ?
N1 C2 H2 123.8 . . ?
N3 C2 H2 123.8 . . ?
C5 C4 N3 105.9(2) . . ?
C5 C4 H4 127.0 . . ?
N3 C4 H4 127.0 . . ?
C4 C5 N1 110.9(3) . . ?
C4 C5 H5 124.6 . . ?
N1 C5 H5 124.6 . . ?
N3 C6 C13 112.3(2) . . ?
N3 C6 C7 110.6(2) . . ?
C13 C6 C7 101.7(2) . . ?
N3 C6 H6 110.6 . . ?
C13 C6 H6 110.6 . . ?
C7 C6 H6 110.6 . . ?
O8 C7 C11 106.4(2) . . ?
O8 C7 C6 110.70(19) . . ?
C11 C7 C6 104.14(19) . . ?
O8 C7 H7 111.7 . . ?
C11 C7 H7 111.7 . . ?
C6 C7 H7 111.7 . . ?
O8 C9 C10 105.9(2) . . ?
O8 C9 H9A 110.6 . . ?
C10 C9 H9A 110.6 . . ?
O8 C9 H9B 110.6 . . ?
C10 C9 H9B 110.6 . . ?
H9A C9 H9B 108.7 . . ?
N14 C10 C9 113.0(2) . . ?
N14 C10 C11 110.5(2) . . ?
C9 C10 C11 102.0(2) . . ?
N14 C10 H10 110.4 . . ?
C9 C10 H10 110.4 . . ?
C11 C10 H10 110.4 . . ?
O12 C11 C7 106.46(19) . . ?
O12 C11 C10 110.5(2) . . ?
C7 C11 C10 104.40(19) . . ?
O12 C11 H11 111.7 . . ?
C7 C11 H11 111.7 . . ?
C10 C11 H11 111.7 . . ?
O12 C13 C6 105.4(2) . . ?
O12 C13 H13A 110.7 . . ?
C6 C13 H13A 110.7 . . ?
O12 C13 H13B 110.7 . . ?
C6 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
N16 C15 N14 112.9(3) . . ?
N16 C15 H15 123.6 . . ?
N14 C15 H15 123.6 . . ?
N16 C17 C18 110.7(2) . . ?
N16 C17 H17 124.6 . . ?
C18 C17 H17 124.6 . . ?
C17 C18 N14 105.5(2) . . ?
C17 C18 H18 127.3 . . ?
N14 C18 H18 127.3 . . ?
C2 N1 C5 104.9(2) . . ?
C2 N3 C4 105.9(2) . . ?
C2 N3 C6 128.1(2) . . ?
C4 N3 C6 125.7(2) . . ?
C15 N14 C18 106.3(2) . . ?
C15 N14 C10 123.8(2) . . ?
C18 N14 C10 129.6(2) . . ?
C15 N16 C17 104.6(2) . . ?
C9 O8 C7 110.47(19) . . ?
C13 O12 C11 109.93(18) . . ?
N21 C22 N23 112.0(2) . . ?
N21 C22 H22 124.0 . . ?
N23 C22 H22 124.0 . . ?
C25 C24 N23 106.1(2) . . ?
C25 C24 H24 127.0 . . ?
N23 C24 H24 127.0 . . ?
C24 C25 N21 110.4(2) . . ?
C24 C25 H25 124.8 . . ?
N21 C25 H25 124.8 . . ?
N23 C26 C33 112.4(2) . . ?
N23 C26 C27 110.06(19) . . ?
C33 C26 C27 102.46(19) . . ?
N23 C26 H26 110.5 . . ?
C33 C26 H26 110.5 . . ?
C27 C26 H26 110.5 . . ?
O28 C27 C31 106.26(19) . . ?
O28 C27 C26 111.08(19) . . ?
C31 C27 C26 103.6(2) . . ?
O28 C27 H27 111.8 . . ?
C31 C27 H27 111.8 . . ?
C26 C27 H27 111.8 . . ?
O28 C29 C30 106.1(2) . . ?
O28 C29 H29A 110.5 . . ?
C30 C29 H29A 110.5 . . ?
O28 C29 H29B 110.5 . . ?
C30 C29 H29B 110.5 . . ?
H29A C29 H29B 108.7 . . ?
N34 C30 C29 112.5(2) . . ?
N34 C30 C31 111.0(2) . . ?
C29 C30 C31 101.64(19) . . ?
N34 C30 H30 110.5 . . ?
C29 C30 H30 110.5 . . ?
C31 C30 H30 110.5 . . ?
O32 C31 C30 110.1(2) . . ?
O32 C31 C27 106.8(2) . . ?
C30 C31 C27 104.9(2) . . ?
O32 C31 H31 111.6 . . ?
C30 C31 H31 111.6 . . ?
C27 C31 H31 111.6 . . ?
O32 C33 C26 105.2(2) . . ?
O32 C33 H33A 110.7 . . ?
C26 C33 H33A 110.7 . . ?
O32 C33 H33B 110.7 . . ?
C26 C33 H33B 110.7 . . ?
H33A C33 H33B 108.8 . . ?
N36 C35 N34 112.9(2) . . ?
N36 C35 H35 123.6 . . ?
N34 C35 H35 123.6 . . ?
C38 C37 N36 110.2(3) . . ?
C38 C37 H37 124.9 . . ?
N36 C37 H37 124.9 . . ?
C37 C38 N34 106.7(2) . . ?
C37 C38 H38 126.7 . . ?
N34 C38 H38 126.7 . . ?
C22 N21 C25 104.8(2) . . ?
C22 N23 C24 106.7(2) . . ?
C22 N23 C26 127.9(2) . . ?
C24 N23 C26 125.0(2) . . ?
C35 N34 C38 105.7(2) . . ?
C35 N34 C30 124.5(2) . . ?
C38 N34 C30 129.7(2) . . ?
C35 N36 C37 104.5(2) . . ?
C27 O28 C29 110.21(19) . . ?
C31 O32 C33 110.2(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.614
_refine_diff_density_min   -0.602
_refine_diff_density_rms    0.201
