 
data_2009src1152
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C22 H18 N4 O4'
_chemical_formula_sum
 'C22 H18 N4 O4'
_chemical_formula_weight          402.40
 
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'
_symmetry_space_group_name_Hall   '-P 1'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    8.3907(5)
_cell_length_b                    8.7207(4)
_cell_length_c                    15.3024(9)
_cell_angle_alpha                 87.410(4)
_cell_angle_beta                  75.837(3)
_cell_angle_gamma                 62.831(3)
_cell_volume                      963.02(9)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     21669
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.14
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.388
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              420
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.9864
_exptl_absorpt_correction_T_max   0.9990
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)'

 
_exptl_special_details
;
SADABS was used to perform the Absorption correction
Parameter refinement on 11698 reflections reduced R(int) from 0.1665 to 0.0825
Ratio of minimum to maximum apparent transmission:  0.664294
The given Tmin and Tmax were generated using the SHELX SIZE command
;
 
_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 to fill the asymmetric unit'
_diffrn_detector_area_resol_mean  66.065
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             15539
_diffrn_reflns_av_R_equivalents   0.1087
_diffrn_reflns_av_sigmaI/netI     0.0995
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.92
_diffrn_reflns_theta_max          25.00
_reflns_number_total              3379
_reflns_number_gt                 2186
_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     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     
'CrystalMaker (CrystalMaker Software Ltd, 2009'
_computing_publication_material   'WINGX (Farrugia, 1998)' 
 
_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)+(0.0382P)²+4.2924P] 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        0.010(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3379
_refine_ls_number_parameters      276
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1629
_refine_ls_R_factor_gt            0.1043
_refine_ls_wR_factor_ref          0.2259
_refine_ls_wR_factor_gt           0.1950
_refine_ls_goodness_of_fit_ref    1.147
_refine_ls_restrained_S_all       1.147
_refine_ls_shift/su_max           0.000
_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 -0.0316(8) 0.6787(6) 0.0956(3) 0.0210(12) Uani 1 1 d . . .
C2 C 0.3020(8) 0.5313(7) 0.0788(4) 0.0253(13) Uani 1 1 d . . .
C3 C 0.2205(7) 0.8333(6) 0.1160(3) 0.0207(12) Uani 1 1 d . . .
C4 C 0.0295(8) 0.9147(6) 0.1332(4) 0.0226(12) Uani 1 1 d . . .
C5 C -0.0630(8) 1.0946(7) 0.1339(4) 0.0274(13) Uani 1 1 d . . .
H5 H -0.1943 1.1525 0.1467 0.033 Uiso 1 1 calc R . .
C6 C 0.0331(8) 1.1880(7) 0.1166(4) 0.0295(14) Uani 1 1 d . . .
H6 H -0.0324 1.3107 0.1201 0.035 Uiso 1 1 calc R . .
C7 C 0.2252(8) 1.1063(7) 0.0938(4) 0.0279(13) Uani 1 1 d . . .
H7 H 0.2918 1.1713 0.0791 0.033 Uiso 1 1 calc R . .
C8 C 0.3179(8) 0.9274(7) 0.0929(4) 0.0253(13) Uani 1 1 d . . .
H8 H 0.4494 0.8692 0.0762 0.030 Uiso 1 1 calc R . .
C9 C -0.2420(7) 0.8809(6) 0.2225(4) 0.0223(12) Uani 1 1 d . . .
C10 C -0.4107(8) 0.9956(7) 0.2070(4) 0.0272(13) Uani 1 1 d . . .
H10 H -0.4176 1.0400 0.1495 0.033 Uiso 1 1 calc R . .
C11 C -0.5699(8) 1.0449(7) 0.2767(4) 0.0303(14) Uani 1 1 d . . .
H11 H -0.6865 1.1247 0.2670 0.036 Uiso 1 1 calc R . .
C12 C -0.5596(8) 0.9780(7) 0.3608(4) 0.0314(14) Uani 1 1 d . . .
H12 H -0.6690 1.0109 0.4081 0.038 Uiso 1 1 calc R . .
C13 C -0.3895(8) 0.8635(8) 0.3750(4) 0.0332(14) Uani 1 1 d . . .
H13 H -0.3821 0.8181 0.4323 0.040 Uiso 1 1 calc R . .
C14 C -0.2315(8) 0.8154(7) 0.3068(4) 0.0283(13) Uani 1 1 d . . .
H14 H -0.1148 0.7374 0.3169 0.034 Uiso 1 1 calc R . .
C15 C 0.4680(8) 0.5880(7) 0.1687(4) 0.0259(13) Uani 1 1 d . . .
H15A H 0.4870 0.6856 0.1855 0.031 Uiso 1 1 calc R . .
H15B H 0.5835 0.5048 0.1263 0.031 Uiso 1 1 calc R . .
C16 C 0.4263(8) 0.4993(7) 0.2537(4) 0.0268(13) Uani 1 1 d . . .
C17 C 0.5598(8) 0.3442(8) 0.3701(4) 0.0303(14) Uani 1 1 d . . .
H17A H 0.5670 0.2300 0.3589 0.036 Uiso 1 1 calc R . .
H17B H 0.4397 0.4167 0.4131 0.036 Uiso 1 1 calc R . .
C18 C 0.7151(8) 0.3231(7) 0.4082(4) 0.0270(13) Uani 1 1 d . . .
C19 C 0.8415(8) 0.3820(7) 0.3728(4) 0.0320(14) Uani 1 1 d . . .
H19 H 0.8360 0.4386 0.3183 0.038 Uiso 1 1 calc R . .
C20 C 0.9761(8) 0.3603(7) 0.4152(4) 0.0322(14) Uani 1 1 d . . .
H20 H 1.0650 0.3997 0.3905 0.039 Uiso 1 1 calc R . .
C21 C 0.9787(8) 0.2780(7) 0.4964(4) 0.0333(14) Uani 1 1 d . . .
H21 H 1.0676 0.2620 0.5288 0.040 Uiso 1 1 calc R . .
C22 C 0.8483(9) 0.2216(8) 0.5269(4) 0.0366(15) Uani 1 1 d . . .
H22 H 0.8530 0.1623 0.5805 0.044 Uiso 1 1 calc R . .
N1 N 0.1461(6) 0.5902(6) 0.0440(3) 0.0231(10) Uani 1 1 d D . .
N2 N 0.3181(6) 0.6516(5) 0.1246(3) 0.0228(10) Uani 1 1 d . . .
N3 N -0.0719(6) 0.8173(5) 0.1515(3) 0.0233(10) Uani 1 1 d . . .
N4 N 0.7158(7) 0.2436(6) 0.4872(3) 0.0329(12) Uani 1 1 d . . .
O1 O -0.1523(5) 0.6379(5) 0.0926(3) 0.0257(9) Uani 1 1 d . . .
O2 O 0.4185(5) 0.3787(5) 0.0670(3) 0.0289(10) Uani 1 1 d . . .
O3 O 0.2810(6) 0.4987(5) 0.2869(3) 0.0344(10) Uani 1 1 d . . .
O4 O 0.5755(5) 0.4264(5) 0.2860(3) 0.0293(10) Uani 1 1 d . . .
H1N H 0.152(8) 0.495(5) 0.008(3) 0.033(16) Uiso 1 1 d 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 O1 1.228(6) . ?
C1 N1 1.368(7) . ?
C1 N3 1.373(6) . ?
C2 O2 1.227(6) . ?
C2 N2 1.361(7) . ?
C2 N1 1.400(7) . ?
C3 C8 1.383(7) . ?
C3 C4 1.383(7) . ?
C3 N2 1.431(6) . ?
C4 C5 1.396(7) . ?
C4 N3 1.430(7) . ?
C5 C6 1.363(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(8) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.383(8) . ?
C9 C14 1.392(8) . ?
C9 N3 1.449(7) . ?
C10 C11 1.387(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.371(8) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 N2 1.446(7) . ?
C15 C16 1.531(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O3 1.203(7) . ?
C16 O4 1.328(7) . ?
C17 O4 1.453(6) . ?
C17 C18 1.488(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N4 1.365(7) . ?
C18 C19 1.369(8) . ?
C19 C20 1.373(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.405(8) . ?
C20 H20 0.9500 . ?
C21 C22 1.369(9) . ?
C21 H21 0.9500 . ?
C22 N4 1.330(7) . ?
C22 H22 0.9500 . ?
N1 H1N 1.00(2) . ?
 
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
O1 C1 N1 122.0(5) . . ?
O1 C1 N3 120.5(5) . . ?
N1 C1 N3 117.4(5) . . ?
O2 C2 N2 122.3(5) . . ?
O2 C2 N1 121.0(5) . . ?
N2 C2 N1 116.7(5) . . ?
C8 C3 C4 120.3(5) . . ?
C8 C3 N2 119.6(5) . . ?
C4 C3 N2 120.1(5) . . ?
C3 C4 C5 118.6(5) . . ?
C3 C4 N3 120.8(4) . . ?
C5 C4 N3 120.5(5) . . ?
C6 C5 C4 120.7(5) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 120.8(5) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 118.6(5) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C3 C8 C7 120.6(5) . . ?
C3 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C14 120.6(5) . . ?
C10 C9 N3 121.8(5) . . ?
C14 C9 N3 117.5(5) . . ?
C9 C10 C11 119.1(5) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 120.3(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 119.8(6) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.2(6) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 120.0(5) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
N2 C15 C16 111.1(4) . . ?
N2 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
N2 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O3 C16 O4 125.5(5) . . ?
O3 C16 C15 125.7(5) . . ?
O4 C16 C15 108.8(5) . . ?
O4 C17 C18 107.7(5) . . ?
O4 C17 H17A 110.2 . . ?
C18 C17 H17A 110.2 . . ?
O4 C17 H17B 110.2 . . ?
C18 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
N4 C18 C19 121.7(5) . . ?
N4 C18 C17 112.7(5) . . ?
C19 C18 C17 125.6(5) . . ?
C18 C19 C20 120.7(6) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C21 118.1(6) . . ?
C19 C20 H20 120.9 . . ?
C21 C20 H20 120.9 . . ?
C22 C21 C20 117.5(6) . . ?
C22 C21 H21 121.2 . . ?
C20 C21 H21 121.2 . . ?
N4 C22 C21 125.1(6) . . ?
N4 C22 H22 117.5 . . ?
C21 C22 H22 117.5 . . ?
C1 N1 C2 123.5(5) . . ?
C1 N1 H1N 107(3) . . ?
C2 N1 H1N 111(3) . . ?
C2 N2 C3 123.1(4) . . ?
C2 N2 C15 116.6(4) . . ?
C3 N2 C15 119.0(4) . . ?
C1 N3 C4 122.6(4) . . ?
C1 N3 C9 117.0(4) . . ?
C4 N3 C9 119.7(4) . . ?
C22 N4 C18 116.9(5) . . ?
C16 O4 C17 117.2(4) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C8 C3 C4 C5 -5.2(8) . . . . ?
N2 C3 C4 C5 173.1(5) . . . . ?
C8 C3 C4 N3 175.9(5) . . . . ?
N2 C3 C4 N3 -5.8(7) . . . . ?
C3 C4 C5 C6 1.1(8) . . . . ?
N3 C4 C5 C6 180.0(5) . . . . ?
C4 C5 C6 C7 2.9(9) . . . . ?
C5 C6 C7 C8 -2.8(8) . . . . ?
C4 C3 C8 C7 5.3(8) . . . . ?
N2 C3 C8 C7 -172.9(5) . . . . ?
C6 C7 C8 C3 -1.3(8) . . . . ?
C14 C9 C10 C11 0.1(8) . . . . ?
N3 C9 C10 C11 176.7(5) . . . . ?
C9 C10 C11 C12 -0.7(8) . . . . ?
C10 C11 C12 C13 0.8(8) . . . . ?
C11 C12 C13 C14 -0.2(9) . . . . ?
C12 C13 C14 C9 -0.4(9) . . . . ?
C10 C9 C14 C13 0.5(8) . . . . ?
N3 C9 C14 C13 -176.3(5) . . . . ?
N2 C15 C16 O3 -8.4(8) . . . . ?
N2 C15 C16 O4 173.1(4) . . . . ?
O4 C17 C18 N4 -178.9(5) . . . . ?
O4 C17 C18 C19 4.1(8) . . . . ?
N4 C18 C19 C20 1.1(9) . . . . ?
C17 C18 C19 C20 177.9(6) . . . . ?
C18 C19 C20 C21 -0.8(9) . . . . ?
C19 C20 C21 C22 1.3(8) . . . . ?
C20 C21 C22 N4 -2.2(9) . . . . ?
O1 C1 N1 C2 -130.7(5) . . . . ?
N3 C1 N1 C2 49.7(7) . . . . ?
O2 C2 N1 C1 125.6(6) . . . . ?
N2 C2 N1 C1 -55.3(7) . . . . ?
O2 C2 N2 C3 160.0(5) . . . . ?
N1 C2 N2 C3 -19.2(7) . . . . ?
O2 C2 N2 C15 -7.3(8) . . . . ?
N1 C2 N2 C15 173.5(5) . . . . ?
C8 C3 N2 C2 -125.4(6) . . . . ?
C4 C3 N2 C2 56.3(7) . . . . ?
C8 C3 N2 C15 41.6(7) . . . . ?
C4 C3 N2 C15 -136.7(5) . . . . ?
C16 C15 N2 C2 -74.0(6) . . . . ?
C16 C15 N2 C3 118.1(5) . . . . ?
O1 C1 N3 C4 -153.3(5) . . . . ?
N1 C1 N3 C4 26.3(7) . . . . ?
O1 C1 N3 C9 16.5(7) . . . . ?
N1 C1 N3 C9 -163.8(4) . . . . ?
C3 C4 N3 C1 -52.3(7) . . . . ?
C5 C4 N3 C1 128.8(5) . . . . ?
C3 C4 N3 C9 138.1(5) . . . . ?
C5 C4 N3 C9 -40.8(7) . . . . ?
C10 C9 N3 C1 -83.8(6) . . . . ?
C14 C9 N3 C1 93.0(6) . . . . ?
C10 C9 N3 C4 86.4(6) . . . . ?
C14 C9 N3 C4 -96.9(6) . . . . ?
C21 C22 N4 C18 2.5(9) . . . . ?
C19 C18 N4 C22 -1.8(8) . . . . ?
C17 C18 N4 C22 -179.0(5) . . . . ?
O3 C16 O4 C17 -2.2(8) . . . . ?
C15 C16 O4 C17 176.3(4) . . . . ?
C18 C17 O4 C16 -162.1(5) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.356
_refine_diff_density_min   -0.386
_refine_diff_density_rms    0.089
