# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 188/245

data_hm1m

_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H14 N2 O2'
_chemical_formula_weight          242.27

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   0.0016
 '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)

loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                    7.776(4)
_cell_length_b                    5.832(3)
_cell_length_c                    14.092(8)
_cell_angle_alpha                 90.00
_cell_angle_beta                  97.65(5)
_cell_angle_gamma                 90.00
_cell_volume                      633.4(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     160(2)
_cell_measurement_reflns_used     32
_cell_measurement_theta_min       1.5
_cell_measurement_theta_max       20

_exptl_crystal_description        'long plate'
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.78
_exptl_crystal_size_mid           0.14
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.270
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              256
_exptl_absorpt_coefficient_mu     0.086
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?

_exptl_special_details
;
 ?
;

_diffrn_ambient_temperature       160(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Siemens SMART CCD diffractometer'
_diffrn_measurement_method        '\w rotation with narrow frames'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          0
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         0
_diffrn_reflns_number             2661
_diffrn_reflns_av_R_equivalents   0.0461
_diffrn_reflns_av_sigmaI/netI     0.0262
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -6
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          2.84
_diffrn_reflns_theta_max          25.26
_reflns_number_total              1139
_reflns_number_gt                 1054
_reflns_threshold_expression      >2sigma(I)

_computing_data_collection        'Siemens SMART'
_computing_cell_refinement        'Siemens SMART'
_computing_data_reduction         'Siemens SAINT'
_computing_structure_solution     'Siemens SHELXTL'
_computing_structure_refinement   'Siemens SHELXTL'
_computing_molecular_graphics     'Siemens SHELXTL'
_computing_publication_material   'SHELXTL and local programs'

_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR 
and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and 
is
 not relevant to the choice of reflections for refinement.  R-factors 
based
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0262P)^2^+0.3872P] where P=(Fo^2^+2Fc^2^)/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        0.037(8)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_abs_structure_details
 'not refined, Friedel pairs merged'
_refine_ls_abs_structure_Flack    ?
_refine_ls_number_reflns          1139
_refine_ls_number_parameters      192
_refine_ls_number_restraints      51
_refine_ls_R_factor_all           0.0588
_refine_ls_R_factor_gt            0.0523
_refine_ls_wR_factor_ref          0.1158
_refine_ls_wR_factor_gt           0.1111
_refine_ls_goodness_of_fit_ref    1.298
_refine_ls_restrained_S_all       1.337
_refine_ls_shift/su_max           0.009
_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
N1 N 0.1572(6) 0.4147(8) 0.7671(3) 0.0394(13) Uani 0.873(6) 1 d PD A 1
N2 N 0.0849(6) 0.6102(8) 0.7419(3) 0.0448(13) Uani 0.873(6) 1 d PD A 1
O1 O 0.3248(4) 0.3653(7) 0.7482(2) 0.0358(10) Uani 0.873(6) 1 d PD A 1
N1X N 0.228(4) 0.416(3) 0.6967(15) 0.047(6) Uani 0.127(6) 1 d PDU A 2
N2X N 0.157(5) 0.586(4) 0.6472(18) 0.067(9) Uani 0.127(6) 1 d PDU A 2
O1X O 0.249(4) 0.369(6) 0.7914(15) 0.067(8) Uani 0.127(6) 1 d PDU A 2
O2 O 0.1659(5) 0.7402(6) 0.6977(3) 0.0634(11) Uani 1 1 d DU . .
C1 C 0.3110(6) 0.2710(10) 0.6466(3) 0.0505(13) Uani 1 1 d DU . .
H1A H 0.2360 0.1332 0.6397 0.061 Uiso 0.873(6) 1 calc PR A 1
H1B H 0.2616 0.3877 0.5997 0.061 Uiso 0.873(6) 1 calc PR A 1
H1C H 0.2545 0.2989 0.5804 0.061 Uiso 0.127(6) 1 calc PR A 2
H1D H 0.2651 0.1210 0.6645 0.061 Uiso 0.127(6) 1 calc PR A 2
C2 C 0.4926(5) 0.2117(9) 0.6313(3) 0.0379(10) Uani 1 1 d . A .
C3 C 0.5886(6) 0.3617(10) 0.5834(3) 0.0484(12) Uani 1 1 d . . .
H3 H 0.5410 0.5052 0.5615 0.058 Uiso 1 1 calc R A .
C4 C 0.7553(7) 0.3009(11) 0.5677(4) 0.0565(15) Uani 1 1 d . A .
H4 H 0.8227 0.4040 0.5357 0.068 Uiso 1 1 calc R . .
C5 C 0.8230(6) 0.0912(11) 0.5985(4) 0.0560(15) Uani 1 1 d . . .
H5 H 0.9357 0.0487 0.5858 0.067 Uiso 1 1 calc R A .
C6 C 0.7286(6) -0.0576(9) 0.6475(3) 0.0486(13) Uani 1 1 d . A .
H6 H 0.7768 -0.2003 0.6702 0.058 Uiso 1 1 calc R . .
C7 C 0.5627(6) 0.0037(9) 0.6634(3) 0.0436(12) Uani 1 1 d . . .
H7 H 0.4965 -0.0983 0.6966 0.052 Uiso 1 1 calc R A .
C8 C 0.0816(6) 0.2481(9) 0.8217(3) 0.0443(12) Uani 1 1 d DU . .
H8A H 0.0756 0.1009 0.7864 0.053 Uiso 0.873(6) 1 calc PR A 1
H8B H -0.0389 0.2956 0.8273 0.053 Uiso 0.873(6) 1 calc PR A 1
H8C H -0.0197 0.3515 0.8202 0.053 Uiso 0.127(6) 1 calc PR A 2
H8D H 0.0493 0.1048 0.7860 0.053 Uiso 0.127(6) 1 calc PR A 2
C9 C 0.1768(5) 0.2084(8) 0.9215(3) 0.0378(10) Uani 1 1 d . A .
C10 C 0.2721(6) 0.0091(9) 0.9432(3) 0.0408(11) Uani 1 1 d . . .
H10 H 0.2810 -0.1017 0.8947 0.049 Uiso 1 1 calc R A .
C11 C 0.3546(6) -0.0286(9) 1.0359(3) 0.0471(12) Uani 1 1 d . A .
H11 H 0.4208 -0.1641 1.0504 0.056 Uiso 1 1 calc R . .
C12 C 0.3399(6) 0.1310(9) 1.1066(3) 0.0475(12) Uani 1 1 d . . .
H12 H 0.3943 0.1042 1.1701 0.057 Uiso 1 1 calc R A .
C13 C 0.2465(6) 0.3290(9) 1.0853(3) 0.0481(13) Uani 1 1 d . A .
H13 H 0.2382 0.4399 1.1339 0.058 Uiso 1 1 calc R . .
C14 C 0.1642(5) 0.3671(9) 0.9928(3) 0.0410(11) Uani 1 1 d . . .
H14 H 0.0989 0.5034 0.9787 0.049 Uiso 1 1 calc R A .

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
N1 0.035(3) 0.043(3) 0.040(3) 0.003(2) 0.004(2) 0.008(2)
N2 0.050(3) 0.036(3) 0.047(3) -0.001(2) 0.003(2) 0.008(2)
O1 0.0259(17) 0.043(2) 0.037(2) -0.0014(19) -0.0020(14) 0.0052(17)
N1X 0.070(18) 0.032(10) 0.040(12) -0.004(9) 0.015(11) -0.010(11)
N2X 0.09(2) 0.043(14) 0.067(18) 0.006(9) 0.003(17) 0.007(13)
O1X 0.09(2) 0.073(19) 0.036(11) 0.000(12) 0.009(13) -0.031(18)
O2 0.069(2) 0.040(2) 0.081(3) 0.015(2) 0.009(2) 0.000(2)
C1 0.048(3) 0.056(3) 0.049(3) 0.002(2) 0.010(2) 0.007(3)
C2 0.041(2) 0.037(2) 0.034(2) 0.000(2) 0.0030(19) -0.002(2)
C3 0.054(3) 0.047(3) 0.043(3) -0.001(3) 0.003(2) -0.003(3)
C4 0.055(3) 0.064(4) 0.051(3) 0.006(3) 0.011(2) -0.022(3)
C5 0.032(3) 0.083(4) 0.052(3) -0.014(3) 0.001(2) -0.003(3)
C6 0.042(3) 0.052(3) 0.049(3) -0.009(2) -0.004(2) 0.007(2)
C7 0.046(3) 0.042(3) 0.043(3) 0.005(2) 0.005(2) 0.001(2)
C8 0.053(3) 0.040(3) 0.040(2) 0.003(2) 0.009(2) 0.007(2)
C9 0.033(2) 0.035(2) 0.046(3) 0.004(2) 0.0074(18) -0.004(2)
C10 0.043(2) 0.036(2) 0.044(2) -0.003(2) 0.008(2) 0.002(2)
C11 0.042(3) 0.039(3) 0.059(3) 0.003(2) 0.004(2) 0.004(2)
C12 0.044(3) 0.053(3) 0.043(3) 0.002(3) -0.001(2) 0.005(2)
C13 0.055(3) 0.046(3) 0.044(3) -0.005(2) 0.008(2) 0.006(3)
C14 0.042(2) 0.038(3) 0.044(2) 0.004(2) 0.0100(18) 0.007(2)

_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
N1 N2 1.300(7) . ?
N1 O1 1.395(5) . ?
N1 C8 1.415(6) . ?
N2 O2 1.210(5) . ?
O1 C1 1.524(6) . ?
N1X N2X 1.29(2) . ?
N1X C1 1.324(17) . ?
N1X O1X 1.351(18) . ?
N2X O2 1.141(19) . ?
O1X C8 1.59(2) . ?
C1 C2 1.498(6) . ?
C2 C3 1.382(7) . ?
C2 C7 1.381(7) . ?
C3 C4 1.390(7) . ?
C4 C5 1.378(8) . ?
C5 C6 1.380(7) . ?
C6 C7 1.385(6) . ?
C8 C9 1.518(6) . ?
C9 C14 1.379(6) . ?
C9 C10 1.390(7) . ?
C10 C11 1.395(6) . ?
C11 C12 1.379(7) . ?
C12 C13 1.376(7) . ?
C13 C14 1.392(6) . ?

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
N2 N1 O1 120.7(4) . . ?
N2 N1 C8 123.7(4) . . ?
O1 N1 C8 115.4(4) . . ?
O2 N2 N1 117.0(4) . . ?
N1 O1 C1 107.7(3) . . ?
N2X N1X C1 113.9(17) . . ?
N2X N1X O1X 132(2) . . ?
C1 N1X O1X 113(2) . . ?
O2 N2X N1X 106.4(19) . . ?
N1X O1X C8 111.1(18) . . ?
N1X C1 C2 139.6(14) . . ?
C2 C1 O1 105.6(4) . . ?
C3 C2 C7 120.1(4) . . ?
C3 C2 C1 120.3(5) . . ?
C7 C2 C1 119.6(4) . . ?
C2 C3 C4 119.5(5) . . ?
C5 C4 C3 120.1(5) . . ?
C4 C5 C6 120.6(5) . . ?
C5 C6 C7 119.2(5) . . ?
C2 C7 C6 120.6(5) . . ?
N1 C8 C9 114.9(4) . . ?
C9 C8 O1X 90.0(9) . . ?
C14 C9 C10 119.2(4) . . ?
C14 C9 C8 120.0(4) . . ?
C10 C9 C8 120.7(4) . . ?
C9 C10 C11 120.2(4) . . ?
C12 C11 C10 119.9(5) . . ?
C13 C12 C11 120.1(4) . . ?
C12 C13 C14 120.1(5) . . ?
C9 C14 C13 120.5(5) . . ?

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
O1 N1 N2 O2 3.5(7) . . . . ?
C8 N1 N2 O2 177.8(5) . . . . ?
N2 N1 O1 C1 -85.1(5) . . . . ?
C8 N1 O1 C1 100.1(5) . . . . ?
C1 N1X N2X O2 -146(3) . . . . ?
O1X N1X N2X O2 26(5) . . . . ?
N2X N1X O1X C8 85(4) . . . . ?
C1 N1X O1X C8 -103(3) . . . . ?
N2X N1X C1 C2 103(3) . . . . ?
O1X N1X C1 C2 -71(2) . . . . ?
N2X N1X C1 O1 147(3) . . . . ?
O1X N1X C1 O1 -26.2(13) . . . . ?
N1 O1 C1 N1X 30.5(15) . . . . ?
N1 O1 C1 C2 -177.7(4) . . . . ?
N1X C1 C2 C7 111.8(14) . . . . ?
O1 C1 C2 C7 83.2(5) . . . . ?
N1X C1 C2 C3 -69.6(14) . . . . ?
O1 C1 C2 C3 -98.2(5) . . . . ?
C7 C2 C3 C4 0.3(7) . . . . ?
C1 C2 C3 C4 -178.3(4) . . . . ?
C2 C3 C4 C5 0.9(7) . . . . ?
C3 C4 C5 C6 -1.9(8) . . . . ?
C4 C5 C6 C7 1.7(7) . . . . ?
C3 C2 C7 C6 -0.5(7) . . . . ?
C1 C2 C7 C6 178.1(4) . . . . ?
C5 C6 C7 C2 -0.5(7) . . . . ?
N2 N1 C8 C9 -112.9(5) . . . . ?
O1 N1 C8 C9 61.7(6) . . . . ?
N2 N1 C8 O1X -149(3) . . . . ?
O1 N1 C8 O1X 25(2) . . . . ?
N1X O1X C8 N1 -39.5(13) . . . . ?
N1X O1X C8 C9 173(3) . . . . ?
N1 C8 C9 C14 75.2(5) . . . . ?
O1X C8 C9 C14 92.4(15) . . . . ?
N1 C8 C9 C10 -107.2(5) . . . . ?
O1X C8 C9 C10 -90.0(15) . . . . ?
C14 C9 C10 C11 -0.4(6) . . . . ?
C8 C9 C10 C11 -178.0(4) . . . . ?
C9 C10 C11 C12 0.8(7) . . . . ?
C10 C11 C12 C13 -1.1(7) . . . . ?
C11 C12 C13 C14 1.0(7) . . . . ?
C10 C9 C14 C13 0.3(7) . . . . ?
C8 C9 C14 C13 177.9(4) . . . . ?
C12 C13 C14 C9 -0.7(7) . . . . ?

_diffrn_measured_fraction_theta_max    0.899
_diffrn_reflns_theta_full              25.26
_diffrn_measured_fraction_theta_full   0.899
_refine_diff_density_max    0.179
_refine_diff_density_min   -0.220
_refine_diff_density_rms    0.041

#===END OF CIF