data_03src0359
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Davies
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H16 N2 O6'
_chemical_formula_weight          356.33
 
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    P2(1)/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                    10.9384(3)
_cell_length_b                    8.2970(2)
_cell_length_c                    17.3097(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  96.667(2)
_cell_angle_gamma                 90.00
_cell_volume                      1560.33(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     6114
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             orange
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.517
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              744
_exptl_absorpt_coefficient_mu     0.116
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9661
_exptl_absorpt_correction_T_max   0.9988
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_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 KappaCCD'
_diffrn_measurement_method        'Φ & ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             14639
_diffrn_reflns_av_R_equivalents   0.0791
_diffrn_reflns_av_sigmaI/netI     0.0651
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          3.09
_diffrn_reflns_theta_max          27.46
_reflns_number_total              3551
_reflns_number_gt                 2748
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'COLLECT (Hooft, 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_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 > 2sigma(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)+(0.0569P)²+0.9341P] 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        0.014(2)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3551
_refine_ls_number_parameters      246
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0716
_refine_ls_R_factor_gt            0.0525
_refine_ls_wR_factor_ref          0.1395
_refine_ls_wR_factor_gt           0.1266
_refine_ls_goodness_of_fit_ref    1.011
_refine_ls_restrained_S_all       1.011
_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 0.82593(15) 0.7376(2) 0.07007(10) 0.0174(4) Uani 1 1 d . . .
C2 C 0.71927(16) 0.8188(2) 0.04022(10) 0.0184(4) Uani 1 1 d . . .
C3 C 0.71094(16) 0.9093(2) -0.03564(10) 0.0199(4) Uani 1 1 d . . .
C4 C 0.81840(16) 0.9150(2) -0.07510(10) 0.0207(4) Uani 1 1 d . . .
H4 H 0.8172 0.9726 -0.1226 0.025 Uiso 1 1 calc R . .
C5 C 0.92138(16) 0.8386(2) -0.04485(10) 0.0182(4) Uani 1 1 d . . .
C6 C 0.93406(15) 0.7466(2) 0.02846(10) 0.0169(4) Uani 1 1 d . . .
C7 C 1.13911(16) 0.6974(2) 0.01355(10) 0.0175(4) Uani 1 1 d . . .
C8 C 1.25447(16) 0.6304(2) 0.04120(10) 0.0186(4) Uani 1 1 d . . .
C9 C 1.35203(17) 0.6416(2) -0.00353(11) 0.0219(4) Uani 1 1 d . . .
H9 H 1.4288 0.5934 0.0145 0.026 Uiso 1 1 calc R . .
C10 C 1.33809(17) 0.7228(2) -0.07458(11) 0.0240(4) Uani 1 1 d . . .
H10 H 1.4057 0.7303 -0.1042 0.029 Uiso 1 1 calc R . .
C11 C 1.22654(17) 0.7925(2) -0.10227(10) 0.0212(4) Uani 1 1 d . . .
H11 H 1.2165 0.8487 -0.1504 0.025 Uiso 1 1 calc R . .
C12 C 1.12997(16) 0.7776(2) -0.05755(10) 0.0184(4) Uani 1 1 d . . .
C13 C 0.82321(16) 0.6495(2) 0.14420(10) 0.0187(4) Uani 1 1 d . . .
C14 C 0.91931(16) 0.4775(2) 0.24095(10) 0.0214(4) Uani 1 1 d . . .
H14A H 0.8487 0.4026 0.2398 0.026 Uiso 1 1 calc R . .
H14B H 0.9131 0.5583 0.2824 0.026 Uiso 1 1 calc R . .
C15 C 1.03915(17) 0.3867(2) 0.25535(10) 0.0236(4) Uani 1 1 d . . .
H15A H 1.0432 0.3061 0.2143 0.035 Uiso 1 1 calc R . .
H15B H 1.0441 0.3327 0.3060 0.035 Uiso 1 1 calc R . .
H15C H 1.1080 0.4622 0.2551 0.035 Uiso 1 1 calc R . .
C16 C 1.27686(15) 0.5581(2) 0.12069(10) 0.0194(4) Uani 1 1 d . . .
C17 C 1.37363(18) 0.3424(2) 0.19545(11) 0.0253(4) Uani 1 1 d . . .
H17A H 1.3949 0.2286 0.1863 0.030 Uiso 1 1 calc R . .
H17B H 1.2995 0.3434 0.2233 0.030 Uiso 1 1 calc R . .
C18 C 1.47816(19) 0.4207(3) 0.24545(12) 0.0303(5) Uani 1 1 d . . .
H18A H 1.5523 0.4178 0.2187 0.045 Uiso 1 1 calc R . .
H18B H 1.4936 0.3626 0.2949 0.045 Uiso 1 1 calc R . .
H18C H 1.4569 0.5330 0.2554 0.045 Uiso 1 1 calc R . .
N1 N 1.03923(13) 0.68058(18) 0.05558(8) 0.0183(3) Uani 1 1 d . . .
N2 N 0.61570(15) 0.8254(2) 0.07322(10) 0.0234(4) Uani 1 1 d . . .
O1 O 1.02024(11) 0.84797(16) -0.08581(7) 0.0205(3) Uani 1 1 d . . .
O2 O 0.61251(12) 0.97444(17) -0.06049(8) 0.0263(3) Uani 1 1 d . . .
O3 O 0.73725(12) 0.66032(17) 0.18411(8) 0.0263(3) Uani 1 1 d . . .
O4 O 0.92006(11) 0.55666(15) 0.16581(7) 0.0202(3) Uani 1 1 d . . .
O5 O 1.24193(12) 0.61644(17) 0.17831(7) 0.0252(3) Uani 1 1 d . . .
O6 O 1.34546(12) 0.42382(15) 0.12053(7) 0.0222(3) Uani 1 1 d . . .
H1N H 0.614(2) 0.774(3) 0.1208(14) 0.033(6) Uiso 1 1 d . . .
H2N H 0.553(2) 0.886(3) 0.0516(13) 0.029(6) Uiso 1 1 d . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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 1.394(2) . ?
C1 C6 1.456(2) . ?
C1 C13 1.480(2) . ?
C2 N2 1.328(2) . ?
C2 C3 1.506(2) . ?
C3 O2 1.236(2) . ?
C3 C4 1.427(2) . ?
C4 C5 1.344(3) . ?
C4 H4 0.9500 . ?
C5 O1 1.362(2) . ?
C5 C6 1.474(2) . ?
C6 N1 1.311(2) . ?
C7 N1 1.388(2) . ?
C7 C12 1.392(2) . ?
C7 C8 1.411(2) . ?
C8 C9 1.392(2) . ?
C8 C16 1.495(2) . ?
C9 C10 1.395(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 O1 1.373(2) . ?
C13 O3 1.233(2) . ?
C13 O4 1.328(2) . ?
C14 O4 1.458(2) . ?
C14 C15 1.508(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O5 1.210(2) . ?
C16 O6 1.343(2) . ?
C17 O6 1.463(2) . ?
C17 C18 1.500(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N2 H1N 0.93(2) . ?
N2 H2N 0.90(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
C2 C1 C6 119.00(16) . . ?
C2 C1 C13 117.38(15) . . ?
C6 C1 C13 123.60(15) . . ?
N2 C2 C1 125.45(17) . . ?
N2 C2 C3 112.71(16) . . ?
C1 C2 C3 121.84(16) . . ?
O2 C3 C4 123.47(17) . . ?
O2 C3 C2 118.89(16) . . ?
C4 C3 C2 117.63(15) . . ?
C5 C4 C3 119.83(16) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 O1 116.75(15) . . ?
C4 C5 C6 124.78(16) . . ?
O1 C5 C6 118.47(15) . . ?
N1 C6 C1 122.06(16) . . ?
N1 C6 C5 121.05(15) . . ?
C1 C6 C5 116.86(15) . . ?
N1 C7 C12 122.08(16) . . ?
N1 C7 C8 120.68(16) . . ?
C12 C7 C8 117.23(16) . . ?
C9 C8 C7 119.90(16) . . ?
C9 C8 C16 118.96(16) . . ?
C7 C8 C16 120.98(15) . . ?
C8 C9 C10 120.66(17) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 120.56(17) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 117.90(17) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
O1 C12 C11 117.05(16) . . ?
O1 C12 C7 119.23(15) . . ?
C11 C12 C7 123.72(16) . . ?
O3 C13 O4 121.30(16) . . ?
O3 C13 C1 122.92(16) . . ?
O4 C13 C1 115.79(15) . . ?
O4 C14 C15 106.13(14) . . ?
O4 C14 H14A 110.5 . . ?
C15 C14 H14A 110.5 . . ?
O4 C14 H14B 110.5 . . ?
C15 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O5 C16 O6 124.29(17) . . ?
O5 C16 C8 124.37(16) . . ?
O6 C16 C8 111.27(15) . . ?
O6 C17 C18 112.31(16) . . ?
O6 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
O6 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 N1 C7 118.80(15) . . ?
C2 N2 H1N 118.2(15) . . ?
C2 N2 H2N 119.6(14) . . ?
H1N N2 H2N 122(2) . . ?
C5 O1 C12 120.28(14) . . ?
C13 O4 C14 115.20(13) . . ?
C16 O6 C17 116.18(14) . . ?
 
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
C6 C1 C2 N2 -177.64(16) . . . . ?
C13 C1 C2 N2 0.9(3) . . . . ?
C6 C1 C2 C3 2.8(3) . . . . ?
C13 C1 C2 C3 -178.70(15) . . . . ?
N2 C2 C3 O2 -2.1(2) . . . . ?
C1 C2 C3 O2 177.56(17) . . . . ?
N2 C2 C3 C4 177.93(16) . . . . ?
C1 C2 C3 C4 -2.4(3) . . . . ?
O2 C3 C4 C5 -178.86(18) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 O1 179.52(16) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C2 C1 C6 N1 176.14(16) . . . . ?
C13 C1 C6 N1 -2.3(3) . . . . ?
C2 C1 C6 C5 -1.9(2) . . . . ?
C13 C1 C6 C5 179.74(16) . . . . ?
C4 C5 C6 N1 -177.37(17) . . . . ?
O1 C5 C6 N1 2.8(2) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
O1 C5 C6 C1 -179.21(15) . . . . ?
N1 C7 C8 C9 176.83(16) . . . . ?
C12 C7 C8 C9 -2.1(3) . . . . ?
N1 C7 C8 C16 -7.8(3) . . . . ?
C12 C7 C8 C16 173.25(16) . . . . ?
C7 C8 C9 C10 2.0(3) . . . . ?
C16 C8 C9 C10 -173.47(17) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 O1 179.76(16) . . . . ?
C10 C11 C12 C7 0.3(3) . . . . ?
N1 C7 C12 O1 2.6(3) . . . . ?
C8 C7 C12 O1 -178.46(15) . . . . ?
N1 C7 C12 C11 -177.92(16) . . . . ?
C8 C7 C12 C11 1.0(3) . . . . ?
C2 C1 C13 O3 -8.4(3) . . . . ?
C6 C1 C13 O3 170.00(17) . . . . ?
C2 C1 C13 O4 171.57(15) . . . . ?
C6 C1 C13 O4 -10.0(2) . . . . ?
C9 C8 C16 O5 133.20(19) . . . . ?
C7 C8 C16 O5 -42.2(3) . . . . ?
C9 C8 C16 O6 -44.0(2) . . . . ?
C7 C8 C16 O6 140.57(17) . . . . ?
C1 C6 N1 C7 -178.51(15) . . . . ?
C5 C6 N1 C7 -0.6(2) . . . . ?
C12 C7 N1 C6 -2.1(3) . . . . ?
C8 C7 N1 C6 179.01(16) . . . . ?
C4 C5 O1 C12 177.90(16) . . . . ?
C6 C5 O1 C12 -2.2(2) . . . . ?
C11 C12 O1 C5 -179.81(15) . . . . ?
C7 C12 O1 C5 -0.3(2) . . . . ?
O3 C13 O4 C14 -3.2(2) . . . . ?
C1 C13 O4 C14 176.81(14) . . . . ?
C15 C14 O4 C13 -177.18(15) . . . . ?
O5 C16 O6 C17 2.6(3) . . . . ?
C8 C16 O6 C17 179.88(14) . . . . ?
C18 C17 O6 C16 -80.3(2) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.46
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.272
_refine_diff_density_min   -0.301
_refine_diff_density_rms    0.064
