data_global
 
_publ_contact_author               'Coles, Simon J.'
_publ_contact_author_email          s.j.coles@soton.ac.uk
 
loop_
_publ_author_name
'Coles, Simon J.'
'Hursthouse, Michael B.'
'Whitby, Richard J.'
'Hunter, Rupert'
_journal_name_full                 'private communication'

data_02sot149
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Hunter / Whitby
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H13 N O3'
_chemical_formula_weight          231.24
 
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            Orthorhombic
_symmetry_space_group_name_H-M    P2(1)2(1)2(1)
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    6.80780(10)
_cell_length_b                    9.3184(2)
_cell_length_c                    17.5481(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1113.21(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     6799
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.14
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.380
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              488
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9710
_exptl_absorpt_correction_T_max   0.9863
_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          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Nonius KappaCCD'
_diffrn_measurement_method        'φ & ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_decay_%         negligible
_diffrn_reflns_number             13466
_diffrn_reflns_av_R_equivalents   0.0450
_diffrn_reflns_av_sigmaI/netI     0.0287
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          3.19
_diffrn_reflns_theta_max          27.47
_reflns_number_total              2538
_reflns_number_gt                 2414
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO & COLLECT'
_computing_data_reduction         'DENZO & COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_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)+(0.0600P)²+0.0912P] 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        0.068(7)
_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    -0.6(8)
_refine_ls_number_reflns          2538
_refine_ls_number_parameters      159
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0337
_refine_ls_R_factor_gt            0.0310
_refine_ls_wR_factor_ref          0.0870
_refine_ls_wR_factor_gt           0.0848
_refine_ls_goodness_of_fit_ref    1.010
_refine_ls_restrained_S_all       1.010
_refine_ls_shift/su_max           0.012
_refine_ls_shift/su_mean          0.001
 
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 0.06418(19) 0.03986(13) 0.68464(7) 0.0278(3) Uani 1 1 d . . .
H1A H -0.0647 0.0023 0.7016 0.033 Uiso 1 1 calc R . .
H1B H 0.1685 -0.0086 0.7143 0.033 Uiso 1 1 calc R . .
C2 C 0.07434(17) 0.25104(12) 0.62510(6) 0.0210(2) Uani 1 1 d . . .
C3 C 0.07366(19) 0.39351(13) 0.60667(7) 0.0250(3) Uani 1 1 d . . .
H3 H 0.0697 0.4663 0.6446 0.030 Uiso 1 1 calc R . .
C4 C 0.07915(18) 0.42614(12) 0.52902(6) 0.0227(2) Uani 1 1 d . . .
H4 H 0.0803 0.5240 0.5139 0.027 Uiso 1 1 calc R . .
C5 C 0.08296(16) 0.32044(11) 0.47310(6) 0.0179(2) Uani 1 1 d . . .
C6 C 0.08643(17) 0.17450(11) 0.49414(6) 0.0193(2) Uani 1 1 d . . .
H6 H 0.0913 0.1002 0.4571 0.023 Uiso 1 1 calc R . .
C7 C 0.08251(17) 0.14499(12) 0.57029(6) 0.0206(2) Uani 1 1 d . . .
C8 C 0.08352(15) 0.36493(11) 0.39346(6) 0.0189(2) Uani 1 1 d . . .
H8 H 0.1051 0.4640 0.3838 0.023 Uiso 1 1 calc R . .
C9 C 0.05682(17) 0.28100(11) 0.33288(6) 0.0189(2) Uani 1 1 d . . .
H9 H 0.0316 0.1816 0.3400 0.023 Uiso 1 1 calc R . .
C10 C 0.06582(17) 0.33973(11) 0.25505(6) 0.0181(2) Uani 1 1 d . . .
C11 C 0.06070(19) 0.27891(13) 0.11941(6) 0.0246(2) Uani 1 1 d . . .
H11A H 0.1387 0.2051 0.0924 0.030 Uiso 1 1 calc R . .
H11B H 0.1310 0.3714 0.1143 0.030 Uiso 1 1 calc R . .
C12 C -0.1355(2) 0.29178(13) 0.08142(7) 0.0271(3) Uani 1 1 d . . .
H12 H -0.1365 0.3163 0.0289 0.032 Uiso 1 1 calc R . .
C13 C -0.3063(2) 0.27201(14) 0.11463(8) 0.0318(3) Uani 1 1 d . . .
H13A H -0.3120 0.2473 0.1671 0.038 Uiso 1 1 calc R . .
H13B H -0.4242 0.2824 0.0862 0.038 Uiso 1 1 calc R . .
N1 N 0.05078(15) 0.24133(10) 0.19943(5) 0.0207(2) Uani 1 1 d . . .
O1 O 0.07317(15) 0.19112(9) 0.69641(4) 0.0291(2) Uani 1 1 d . . .
O2 O 0.09093(14) 0.01307(9) 0.60473(5) 0.0295(2) Uani 1 1 d . . .
O3 O 0.09109(14) 0.46900(8) 0.24144(5) 0.0249(2) Uani 1 1 d . . .
H1N H 0.017(2) 0.1482(18) 0.2124(9) 0.035(4) Uiso 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 0.0308(6) 0.0316(6) 0.0211(5) 0.0058(5) 0.0013(5) 0.0045(6)
C2 0.0188(5) 0.0296(6) 0.0144(5) 0.0010(4) -0.0010(4) -0.0014(5)
C3 0.0295(6) 0.0260(5) 0.0194(5) -0.0046(4) -0.0004(5) -0.0030(5)
C4 0.0253(5) 0.0213(5) 0.0214(5) -0.0018(4) 0.0003(5) -0.0017(5)
C5 0.0148(5) 0.0212(5) 0.0177(5) -0.0015(4) -0.0003(4) -0.0004(4)
C6 0.0202(5) 0.0210(5) 0.0167(5) -0.0013(4) 0.0009(4) 0.0005(4)
C7 0.0174(5) 0.0225(5) 0.0219(5) 0.0024(4) 0.0003(4) 0.0010(5)
C8 0.0174(5) 0.0193(5) 0.0201(5) 0.0007(4) 0.0005(4) 0.0005(4)
C9 0.0202(5) 0.0192(5) 0.0174(5) 0.0012(4) -0.0002(4) 0.0000(5)
C10 0.0174(5) 0.0192(5) 0.0178(5) 0.0001(4) -0.0004(4) 0.0004(5)
C11 0.0329(6) 0.0258(5) 0.0152(5) -0.0010(4) 0.0032(5) -0.0026(5)
C12 0.0426(7) 0.0203(5) 0.0183(5) -0.0001(4) -0.0046(5) 0.0012(5)
C13 0.0361(7) 0.0297(6) 0.0296(6) -0.0005(5) -0.0088(5) 0.0042(6)
N1 0.0276(5) 0.0184(4) 0.0160(4) 0.0000(3) -0.0002(4) -0.0003(4)
O1 0.0372(5) 0.0340(5) 0.0162(4) 0.0036(3) -0.0008(4) -0.0025(4)
O2 0.0422(5) 0.0246(4) 0.0217(4) 0.0053(3) 0.0024(4) 0.0022(4)
O3 0.0370(5) 0.0173(4) 0.0206(4) 0.0008(3) 0.0014(3) -0.0011(4)
 
_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 O1 1.4258(15) . ?
C1 O2 1.4359(14) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.3665(17) . ?
C2 O1 1.3703(13) . ?
C2 C7 1.3802(16) . ?
C3 C4 1.3967(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3906(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.4094(15) . ?
C5 C8 1.4578(14) . ?
C6 C7 1.3645(15) . ?
C6 H6 0.9500 . ?
C7 O2 1.3710(13) . ?
C8 C9 1.3321(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.4726(14) . ?
C9 H9 0.9500 . ?
C10 O3 1.2401(13) . ?
C10 N1 1.3431(14) . ?
C11 N1 1.4488(14) . ?
C11 C12 1.4976(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.3139(19) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9500 . ?
C13 H13B 0.9500 . ?
N1 H1N 0.926(17) . ?
 
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 O2 107.93(9) . . ?
O1 C1 H1A 110.1 . . ?
O2 C1 H1A 110.1 . . ?
O1 C1 H1B 110.1 . . ?
O2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
C3 C2 O1 127.73(10) . . ?
C3 C2 C7 122.07(10) . . ?
O1 C2 C7 110.18(10) . . ?
C2 C3 C4 116.25(10) . . ?
C2 C3 H3 121.9 . . ?
C4 C3 H3 121.9 . . ?
C5 C4 C3 122.33(10) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 119.93(10) . . ?
C4 C5 C8 118.37(10) . . ?
C6 C5 C8 121.70(10) . . ?
C7 C6 C5 116.78(10) . . ?
C7 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
C6 C7 O2 127.70(10) . . ?
C6 C7 C2 122.62(10) . . ?
O2 C7 C2 109.66(10) . . ?
C9 C8 C5 126.70(10) . . ?
C9 C8 H8 116.6 . . ?
C5 C8 H8 116.6 . . ?
C8 C9 C10 121.08(10) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
O3 C10 N1 122.26(10) . . ?
O3 C10 C9 123.05(10) . . ?
N1 C10 C9 114.65(9) . . ?
N1 C11 C12 114.16(10) . . ?
N1 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
N1 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 125.51(11) . . ?
C13 C12 H12 117.2 . . ?
C11 C12 H12 117.2 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C10 N1 C11 122.40(9) . . ?
C10 N1 H1N 118.7(10) . . ?
C11 N1 H1N 118.4(10) . . ?
C2 O1 C1 105.71(8) . . ?
C7 O2 C1 105.62(9) . . ?
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              27.47
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.222
_refine_diff_density_min   -0.164
_refine_diff_density_rms    0.034
