 
data_2009src0189
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H8 N2 O4'
_chemical_formula_weight          244.20
 
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                    7.7644(2)
_cell_length_b                    8.7396(3)
_cell_length_c                    9.6184(3)
_cell_angle_alpha                 108.0280(10)
_cell_angle_beta                  96.346(2)
_cell_angle_gamma                 107.648(2)
_cell_volume                      576.19(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     7330
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.37
_exptl_crystal_size_min           0.21
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.408
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              252
_exptl_absorpt_coefficient_mu     0.108
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9579
_exptl_absorpt_correction_T_max   0.9776
_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             14073
_diffrn_reflns_av_R_equivalents   0.0400
_diffrn_reflns_av_sigmaI/netI     0.0305
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          3.09
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2622
_reflns_number_gt                 2173
_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)+(0.0594P)²+0.2416P] 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          2622
_refine_ls_number_parameters      165
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0544
_refine_ls_R_factor_gt            0.0439
_refine_ls_wR_factor_ref          0.1206
_refine_ls_wR_factor_gt           0.1133
_refine_ls_goodness_of_fit_ref    1.049
_refine_ls_restrained_S_all       1.049
_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 -0.1191(2) -0.33899(19) -0.49227(17) 0.0279(3) Uani 1 1 d . . .
H1A H -0.2405 -0.3298 -0.5170 0.042 Uiso 1 1 calc R . .
H1B H -0.1268 -0.4135 -0.4334 0.042 Uiso 1 1 calc R . .
H1C H -0.0819 -0.3884 -0.5850 0.042 Uiso 1 1 calc R . .
C2 C 0.02044(19) -0.16481(18) -0.40326(15) 0.0205(3) Uani 1 1 d . . .
C4 C 0.10772(19) 0.05260(17) -0.16034(15) 0.0186(3) Uani 1 1 d . . .
C5 C 0.08269(19) 0.19507(18) -0.18193(16) 0.0208(3) Uani 1 1 d . . .
H5 H -0.0010 0.1806 -0.2689 0.025 Uiso 1 1 calc R . .
C6 C 0.18013(19) 0.35848(18) -0.07625(16) 0.0208(3) Uani 1 1 d . . .
H6 H 0.1653 0.4566 -0.0912 0.025 Uiso 1 1 calc R . .
C7 C 0.29967(18) 0.37775(17) 0.05177(15) 0.0183(3) Uani 1 1 d . . .
C8 C 0.32527(18) 0.23652(18) 0.07538(15) 0.0186(3) Uani 1 1 d . . .
C9 C 0.22914(18) 0.07065(17) -0.03398(15) 0.0183(3) Uani 1 1 d . . .
C10 C 0.2554(2) -0.07770(18) -0.01356(16) 0.0216(3) Uani 1 1 d . . .
C12 C 0.4443(2) 0.25919(19) 0.21141(17) 0.0238(3) Uani 1 1 d . . .
C15 C 0.30751(19) 0.62712(17) 0.24287(15) 0.0187(3) Uani 1 1 d . . .
C16 C 0.4329(2) 0.80338(19) 0.34257(16) 0.0246(3) Uani 1 1 d . . .
H16A H 0.3644 0.8824 0.3548 0.037 Uiso 1 1 calc R . .
H16B H 0.5375 0.8422 0.2978 0.037 Uiso 1 1 calc R . .
H16C H 0.4796 0.8017 0.4408 0.037 Uiso 1 1 calc R . .
N11 N 0.27841(19) -0.19418(17) 0.00492(16) 0.0295(3) Uani 1 1 d . . .
N13 N 0.5361(2) 0.2757(2) 0.32100(16) 0.0371(4) Uani 1 1 d . . .
O2 O 0.13563(15) -0.07479(14) -0.44476(12) 0.0275(3) Uani 1 1 d . . .
O3 O -0.00044(14) -0.11374(13) -0.25656(11) 0.0225(2) Uani 1 1 d . . .
O14 O 0.40399(13) 0.54028(12) 0.15707(11) 0.0211(2) Uani 1 1 d . . .
O15 O 0.14545(14) 0.56060(13) 0.23457(12) 0.0247(3) Uani 1 1 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 0.0320(8) 0.0212(7) 0.0228(7) 0.0034(6) 0.0046(6) 0.0045(6)
C2 0.0219(7) 0.0214(7) 0.0185(7) 0.0055(6) 0.0038(5) 0.0101(6)
C4 0.0188(7) 0.0177(7) 0.0169(6) 0.0041(5) 0.0073(5) 0.0044(5)
C5 0.0213(7) 0.0222(7) 0.0188(7) 0.0074(6) 0.0049(5) 0.0078(6)
C6 0.0221(7) 0.0202(7) 0.0228(7) 0.0087(6) 0.0079(6) 0.0094(6)
C7 0.0169(6) 0.0164(6) 0.0201(7) 0.0042(5) 0.0075(5) 0.0050(5)
C8 0.0183(7) 0.0214(7) 0.0174(7) 0.0071(6) 0.0070(5) 0.0080(5)
C9 0.0195(7) 0.0179(7) 0.0197(7) 0.0071(5) 0.0093(5) 0.0076(5)
C10 0.0224(7) 0.0212(7) 0.0204(7) 0.0066(6) 0.0069(5) 0.0069(6)
C12 0.0254(7) 0.0215(7) 0.0234(7) 0.0074(6) 0.0064(6) 0.0073(6)
C15 0.0228(7) 0.0197(7) 0.0158(6) 0.0072(5) 0.0044(5) 0.0096(6)
C16 0.0261(7) 0.0199(7) 0.0211(7) 0.0015(6) 0.0028(6) 0.0058(6)
N11 0.0335(7) 0.0246(7) 0.0335(7) 0.0127(6) 0.0091(6) 0.0120(6)
N13 0.0411(8) 0.0362(8) 0.0281(7) 0.0112(6) -0.0027(6) 0.0101(7)
O2 0.0283(6) 0.0254(6) 0.0245(5) 0.0058(4) 0.0103(4) 0.0055(4)
O3 0.0264(5) 0.0175(5) 0.0178(5) 0.0036(4) 0.0056(4) 0.0026(4)
O14 0.0189(5) 0.0166(5) 0.0234(5) 0.0023(4) 0.0052(4) 0.0054(4)
O15 0.0215(5) 0.0240(5) 0.0252(5) 0.0050(4) 0.0072(4) 0.0070(4)
 
_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 C2 1.487(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.1937(18) . ?
C2 O3 1.3861(17) . ?
C4 C9 1.3888(19) . ?
C4 C5 1.389(2) . ?
C4 O3 1.3894(16) . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(2) . ?
C7 O14 1.3893(16) . ?
C8 C9 1.4112(19) . ?
C8 C12 1.438(2) . ?
C9 C10 1.439(2) . ?
C10 N11 1.147(2) . ?
C12 N13 1.148(2) . ?
C15 O15 1.1972(17) . ?
C15 O14 1.3827(17) . ?
C15 C16 1.4868(19) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O3 121.91(13) . . ?
O2 C2 C1 128.14(13) . . ?
O3 C2 C1 109.95(12) . . ?
C9 C4 C5 121.10(13) . . ?
C9 C4 O3 117.43(12) . . ?
C5 C4 O3 121.19(12) . . ?
C6 C5 C4 119.84(13) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 119.54(13) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 O14 117.83(12) . . ?
C8 C7 C6 121.29(13) . . ?
O14 C7 C6 120.82(12) . . ?
C7 C8 C9 119.08(12) . . ?
C7 C8 C12 120.21(13) . . ?
C9 C8 C12 120.69(12) . . ?
C4 C9 C8 119.13(12) . . ?
C4 C9 C10 120.62(12) . . ?
C8 C9 C10 120.25(12) . . ?
N11 C10 C9 178.87(16) . . ?
N13 C12 C8 178.53(16) . . ?
O15 C15 O14 121.64(12) . . ?
O15 C15 C16 127.58(13) . . ?
O14 C15 C16 110.76(11) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 O3 C4 117.84(10) . . ?
C15 O14 C7 116.35(10) . . ?
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.380
_refine_diff_density_min   -0.332
_refine_diff_density_rms    0.051
