# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 1999
# CCDC Number: 207/350

data_3h 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C20 H21 F2 N O3' 
_chemical_formula_weight          361.38 
_chemical_melting_point           ? 
_chemical_compound_source         ? 
 
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' 
 'F'  'F'   0.0171   0.0103 
 '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                    7.7023(13) 
_cell_length_b                    9.925(2) 
_cell_length_c                    13.356(2) 
_cell_angle_alpha                 80.96(3) 
_cell_angle_beta                  76.495(11) 
_cell_angle_gamma                 70.767(13) 
_cell_volume                      933.8(3) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.285 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              380 
_exptl_absorpt_coefficient_mu     0.099 
_exptl_absorpt_correction_type    'Empirical, DIFABS'
_exptl_absorpt_correction_T_min   1.098
_exptl_absorpt_correction_T_max   1.369
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(2) 
_diffrn_radiation_wavelength      0.71069 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        'Enraf Nonius FAST TV area detector'
_diffrn_measurement_method        ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             3767 
_diffrn_reflns_av_R_equivalents   0.0791 
_diffrn_reflns_av_sigmaI/netI     0.1469 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        10 
_diffrn_reflns_theta_min          2.18 
_diffrn_reflns_theta_max          24.85 
_reflns_number_total              2431 
_reflns_number_observed           1311 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-92 (Sheldrick, 1993)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses 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 observed criterion 
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.0000P] 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     ? 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          2431 
_refine_ls_number_parameters      241 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0783 
_refine_ls_R_factor_obs           0.0429 
_refine_ls_wR_factor_all          0.1054 
_refine_ls_wR_factor_obs          0.0975 
_refine_ls_goodness_of_fit_all    0.648 
_refine_ls_goodness_of_fit_obs    0.852 
_refine_ls_restrained_S_all       0.648 
_refine_ls_restrained_S_obs       0.852 
_refine_ls_shift/esd_max          0.001 
_refine_ls_shift/esd_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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
F1 F 0.1206(3) 0.1108(2) 1.00410(14) 0.0560(7) Uani 1 d . . 
F2 F 0.3866(3) 0.1469(2) 0.99773(14) 0.0525(6) Uani 1 d . . 
O1 O -0.0468(3) 0.4888(2) 0.8277(2) 0.0374(7) Uani 1 d . . 
O2 O 0.3355(3) 0.3536(2) 0.83792(15) 0.0297(6) Uani 1 d . . 
O3 O 0.2183(3) 0.5073(2) 0.9645(2) 0.0392(7) Uani 1 d . . 
N1 N 0.4536(4) 0.5352(3) 0.8309(2) 0.0330(8) Uani 1 d . . 
C1 C 0.0652(4) 0.2815(3) 0.7308(2) 0.0255(8) Uani 1 d . . 
C2 C 0.0754(5) 0.1414(4) 0.7245(2) 0.0323(9) Uani 1 d . . 
H2 H 0.0509(5) 0.0824(4) 0.7860(2) 0.039 Uiso 1 calc R . 
C3 C 0.1210(4) 0.0855(4) 0.6291(2) 0.0307(9) Uani 1 d . . 
H3 H 0.1267(4) -0.0110(4) 0.6265(2) 0.037 Uiso 1 calc R . 
C4 C 0.1582(4) 0.1682(3) 0.5382(2) 0.0252(8) Uani 1 d . . 
C5 C 0.2127(5) 0.1071(3) 0.4359(2) 0.0274(9) Uani 1 d . . 
C6 C 0.3362(5) -0.0309(4) 0.4246(3) 0.0341(9) Uani 1 d . . 
H6 H 0.3839(5) -0.0861(4) 0.4826(3) 0.041 Uiso 1 calc R . 
C7 C 0.3906(5) -0.0891(4) 0.3298(3) 0.0403(10) Uani 1 d . . 
H7 H 0.4750(5) -0.1832(4) 0.3232(3) 0.048 Uiso 1 calc R . 
C8 C 0.3214(5) -0.0095(4) 0.2458(3) 0.0397(10) Uani 1 d . . 
H8 H 0.3588(5) -0.0489(4) 0.1809(3) 0.048 Uiso 1 calc R . 
C9 C 0.1973(5) 0.1280(4) 0.2550(3) 0.0379(10) Uani 1 d . . 
H9 H 0.1480(5) 0.1822(4) 0.1971(3) 0.045 Uiso 1 calc R . 
C10 C 0.1463(5) 0.1854(4) 0.3499(2) 0.0311(9) Uani 1 d . . 
H10 H 0.0640(5) 0.2803(4) 0.3558(2) 0.037 Uiso 1 calc R . 
C11 C 0.1434(4) 0.3113(3) 0.5445(2) 0.0290(9) Uani 1 d . . 
H11 H 0.1645(4) 0.3711(3) 0.4830(2) 0.035 Uiso 1 calc R . 
C12 C 0.0981(4) 0.3667(3) 0.6400(2) 0.0292(9) Uani 1 d . . 
H12 H 0.0896(4) 0.4637(3) 0.6431(2) 0.035 Uiso 1 calc R . 
C13 C 0.0245(5) 0.3361(3) 0.8371(2) 0.0295(9) Uani 1 d . . 
H13 H -0.0725(5) 0.2969(3) 0.8842(2) 0.035 Uiso 1 calc R . 
C14 C 0.1974(5) 0.2894(3) 0.8824(2) 0.0253(8) Uani 1 d . . 
C15 C 0.2331(6) 0.1884(4) 0.9571(3) 0.0357(10) Uani 1 d . . 
C16 C 0.3273(5) 0.4724(3) 0.8839(2) 0.0293(9) Uani 1 d . . 
C17 C 0.4599(5) 0.6633(4) 0.8714(3) 0.0395(10) Uani 1 d . . 
H17A H 0.5904(5) 0.6672(4) 0.8532(3) 0.047 Uiso 1 calc R . 
H17B H 0.4246(5) 0.6532(4) 0.9477(3) 0.047 Uiso 1 calc R . 
C18 C 0.3345(6) 0.8014(4) 0.8319(3) 0.0685(14) Uani 1 d . . 
H18A H 0.3389(27) 0.8801(5) 0.8663(14) 0.103 Uiso 1 calc R . 
H18B H 0.2056(8) 0.7970(10) 0.8462(17) 0.103 Uiso 1 calc R . 
H18C H 0.3765(21) 0.8177(13) 0.7571(5) 0.103 Uiso 1 calc R . 
C19 C 0.5743(5) 0.4898(4) 0.7333(3) 0.0507(12) Uani 1 d . . 
H19A H 0.6189(5) 0.3838(4) 0.7377(3) 0.061 Uiso 1 calc R . 
H19B H 0.6855(5) 0.5234(4) 0.7223(3) 0.061 Uiso 1 calc R . 
C20 C 0.4808(7) 0.5445(6) 0.6410(3) 0.096(2) Uani 1 d . . 
H20A H 0.5710(15) 0.5113(30) 0.5781(4) 0.144 Uiso 1 calc R . 
H20B H 0.4371(41) 0.6495(6) 0.6354(15) 0.144 Uiso 1 calc R . 
H20C H 0.3738(29) 0.5082(29) 0.6495(12) 0.144 Uiso 1 calc R . 
H1 H -0.1014(53) 0.5165(39) 0.8922(28) 0.073(14) Uiso 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 
F1 0.088(2) 0.0478(15) 0.0337(12) 0.0044(10) -0.0060(12) -0.0306(14) 
F2 0.065(2) 0.0522(15) 0.0338(13) -0.0013(10) -0.0232(12) -0.0011(12) 
O1 0.044(2) 0.031(2) 0.0286(15) -0.0118(12) -0.0062(12) 0.0034(12) 
O2 0.0331(14) 0.0319(14) 0.0246(13) -0.0118(11) 0.0007(11) -0.0108(12) 
O3 0.048(2) 0.040(2) 0.0275(14) -0.0149(12) 0.0057(12) -0.0149(13) 
N1 0.032(2) 0.040(2) 0.030(2) -0.0085(14) -0.0019(14) -0.014(2) 
C1 0.025(2) 0.030(2) 0.021(2) -0.008(2) -0.001(2) -0.007(2) 
C2 0.043(2) 0.034(2) 0.021(2) -0.002(2) -0.003(2) -0.015(2) 
C3 0.038(2) 0.028(2) 0.028(2) -0.005(2) -0.005(2) -0.013(2) 
C4 0.030(2) 0.026(2) 0.020(2) -0.007(2) -0.004(2) -0.008(2) 
C5 0.028(2) 0.029(2) 0.027(2) -0.009(2) -0.002(2) -0.011(2) 
C6 0.035(2) 0.036(2) 0.032(2) -0.008(2) -0.009(2) -0.007(2) 
C7 0.045(3) 0.035(2) 0.038(2) -0.016(2) -0.001(2) -0.007(2) 
C8 0.046(3) 0.049(3) 0.027(2) -0.015(2) 0.008(2) -0.023(2) 
C9 0.044(3) 0.046(2) 0.029(2) -0.006(2) -0.003(2) -0.021(2) 
C10 0.037(2) 0.029(2) 0.025(2) -0.005(2) -0.006(2) -0.007(2) 
C11 0.038(2) 0.027(2) 0.021(2) -0.000(2) -0.005(2) -0.010(2) 
C12 0.038(2) 0.024(2) 0.027(2) -0.009(2) -0.003(2) -0.010(2) 
C13 0.033(2) 0.030(2) 0.023(2) -0.008(2) -0.001(2) -0.008(2) 
C14 0.031(2) 0.023(2) 0.021(2) -0.006(2) -0.002(2) -0.006(2) 
C15 0.046(3) 0.034(3) 0.028(2) -0.009(2) -0.002(2) -0.013(2) 
C16 0.033(2) 0.027(2) 0.026(2) -0.007(2) -0.006(2) -0.005(2) 
C17 0.041(2) 0.036(2) 0.046(2) -0.006(2) -0.010(2) -0.016(2) 
C18 0.054(3) 0.038(3) 0.116(4) -0.004(3) -0.034(3) -0.006(2) 
C19 0.040(3) 0.075(3) 0.040(2) -0.020(2) 0.010(2) -0.028(2) 
C20 0.093(4) 0.195(6) 0.027(3) -0.009(3) -0.007(3) -0.083(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 
F1 C15 1.332(4) . ? 
F2 C15 1.330(4) . ? 
O1 C13 1.427(4) . ? 
O1 H1 0.91(3) . ? 
O2 C14 1.386(4) . ? 
O2 C16 1.390(3) . ? 
O3 C16 1.219(3) . ? 
N1 C16 1.332(4) . ? 
N1 C19 1.453(4) . ? 
N1 C17 1.476(4) . ? 
C1 C2 1.382(4) . ? 
C1 C12 1.387(4) . ? 
C1 C13 1.526(4) . ? 
C2 C3 1.393(4) . ? 
C2 H2 0.95 . ? 
C3 C4 1.382(4) . ? 
C3 H3 0.95 . ? 
C4 C11 1.401(4) . ? 
C4 C5 1.494(4) . ? 
C5 C10 1.385(4) . ? 
C5 C6 1.394(4) . ? 
C6 C7 1.390(4) . ? 
C6 H6 0.95 . ? 
C7 C8 1.375(5) . ? 
C7 H7 0.95 . ? 
C8 C9 1.390(5) . ? 
C8 H8 0.95 . ? 
C9 C10 1.390(4) . ? 
C9 H9 0.95 . ? 
C10 H10 0.95 . ? 
C11 C12 1.392(4) . ? 
C11 H11 0.95 . ? 
C12 H12 0.95 . ? 
C13 C14 1.495(4) . ? 
C13 H13 1.00 . ? 
C14 C15 1.307(5) . ? 
C17 C18 1.493(5) . ? 
C17 H17A 0.99 . ? 
C17 H17B 0.99 . ? 
C18 H18A 0.98 . ? 
C18 H18B 0.98 . ? 
C18 H18C 0.98 . ? 
C19 C20 1.510(5) . ? 
C19 H19A 0.99 . ? 
C19 H19B 0.99 . ? 
C20 H20A 0.98 . ? 
C20 H20B 0.98 . ? 
C20 H20C 0.98 . ? 
 
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 
C13 O1 H1 107.1(23) . . ? 
C14 O2 C16 115.6(2) . . ? 
C16 N1 C19 123.4(3) . . ? 
C16 N1 C17 117.2(3) . . ? 
C19 N1 C17 119.2(3) . . ? 
C2 C1 C12 118.7(3) . . ? 
C2 C1 C13 119.1(3) . . ? 
C12 C1 C13 122.1(3) . . ? 
C1 C2 C3 120.8(3) . . ? 
C1 C2 H2 119.6(2) . . ? 
C3 C2 H2 119.6(2) . . ? 
C4 C3 C2 121.0(3) . . ? 
C4 C3 H3 119.5(2) . . ? 
C2 C3 H3 119.5(2) . . ? 
C3 C4 C11 118.1(3) . . ? 
C3 C4 C5 121.1(3) . . ? 
C11 C4 C5 120.9(3) . . ? 
C10 C5 C6 118.1(3) . . ? 
C10 C5 C4 121.7(3) . . ? 
C6 C5 C4 120.2(3) . . ? 
C7 C6 C5 121.1(3) . . ? 
C7 C6 H6 119.4(2) . . ? 
C5 C6 H6 119.4(2) . . ? 
C8 C7 C6 119.6(3) . . ? 
C8 C7 H7 120.2(2) . . ? 
C6 C7 H7 120.2(2) . . ? 
C7 C8 C9 120.5(3) . . ? 
C7 C8 H8 119.7(2) . . ? 
C9 C8 H8 119.7(2) . . ? 
C8 C9 C10 119.2(4) . . ? 
C8 C9 H9 120.4(2) . . ? 
C10 C9 H9 120.4(2) . . ? 
C5 C10 C9 121.4(3) . . ? 
C5 C10 H10 119.3(2) . . ? 
C9 C10 H10 119.3(2) . . ? 
C12 C11 C4 120.7(3) . . ? 
C12 C11 H11 119.6(2) . . ? 
C4 C11 H11 119.6(2) . . ? 
C1 C12 C11 120.6(3) . . ? 
C1 C12 H12 119.7(2) . . ? 
C11 C12 H12 119.7(2) . . ? 
O1 C13 C14 109.8(3) . . ? 
O1 C13 C1 109.2(3) . . ? 
C14 C13 C1 111.1(3) . . ? 
O1 C13 H13 108.9(2) . . ? 
C14 C13 H13 108.9(2) . . ? 
C1 C13 H13 108.9(2) . . ? 
C15 C14 O2 117.2(3) . . ? 
C15 C14 C13 125.5(4) . . ? 
O2 C14 C13 117.2(3) . . ? 
C14 C15 F2 125.6(4) . . ? 
C14 C15 F1 124.9(4) . . ? 
F2 C15 F1 109.5(3) . . ? 
O3 C16 N1 126.8(3) . . ? 
O3 C16 O2 121.5(3) . . ? 
N1 C16 O2 111.6(3) . . ? 
N1 C17 C18 114.4(3) . . ? 
N1 C17 H17A 108.7(2) . . ? 
C18 C17 H17A 108.7(2) . . ? 
N1 C17 H17B 108.7(2) . . ? 
C18 C17 H17B 108.7(2) . . ? 
H17A C17 H17B 107.6 . . ? 
C17 C18 H18A 109.5(2) . . ? 
C17 C18 H18B 109.5(2) . . ? 
H18A C18 H18B 109.5 . . ? 
C17 C18 H18C 109.5(2) . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 109.5 . . ? 
N1 C19 C20 114.1(3) . . ? 
N1 C19 H19A 108.7(2) . . ? 
C20 C19 H19A 108.7(2) . . ? 
N1 C19 H19B 108.7(2) . . ? 
C20 C19 H19B 108.7(2) . . ? 
H19A C19 H19B 107.6 . . ? 
C19 C20 H20A 109.5(2) . . ? 
C19 C20 H20B 109.5(3) . . ? 
H20A C20 H20B 109.5 . . ? 
C19 C20 H20C 109.5(2) . . ? 
H20A C20 H20C 109.5 . . ? 
H20B C20 H20C 109.5 . . ? 
 
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 
 C12 C1 C2 C3 1.1(5) . . . . ? 
 C13 C1 C2 C3 -176.9(3) . . . . ? 
 C1 C2 C3 C4 0.3(5) . . . . ? 
 C2 C3 C4 C11 -1.8(5) . . . . ? 
 C2 C3 C4 C5 178.2(3) . . . . ? 
 C3 C4 C5 C10 140.4(3) . . . . ? 
 C11 C4 C5 C10 -39.6(5) . . . . ? 
 C3 C4 C5 C6 -40.9(5) . . . . ? 
 C11 C4 C5 C6 139.1(3) . . . . ? 
 C10 C5 C6 C7 -0.4(5) . . . . ? 
 C4 C5 C6 C7 -179.2(3) . . . . ? 
 C5 C6 C7 C8 -0.1(5) . . . . ? 
 C6 C7 C8 C9 -0.2(5) . . . . ? 
 C7 C8 C9 C10 1.1(5) . . . . ? 
 C6 C5 C10 C9 1.3(5) . . . . ? 
 C4 C5 C10 C9 -180.0(3) . . . . ? 
 C8 C9 C10 C5 -1.6(5) . . . . ? 
 C3 C4 C11 C12 1.9(5) . . . . ? 
 C5 C4 C11 C12 -178.1(3) . . . . ? 
 C2 C1 C12 C11 -1.0(5) . . . . ? 
 C13 C1 C12 C11 177.0(3) . . . . ? 
 C4 C11 C12 C1 -0.5(5) . . . . ? 
 C2 C1 C13 O1 -158.9(3) . . . . ? 
 C12 C1 C13 O1 23.2(4) . . . . ? 
 C2 C1 C13 C14 79.9(4) . . . . ? 
 C12 C1 C13 C14 -98.1(4) . . . . ? 
 C16 O2 C14 C15 -89.5(3) . . . . ? 
 C16 O2 C14 C13 93.7(3) . . . . ? 
 O1 C13 C14 C15 133.7(3) . . . . ? 
 C1 C13 C14 C15 -105.4(4) . . . . ? 
 O1 C13 C14 O2 -49.8(3) . . . . ? 
 C1 C13 C14 O2 71.1(3) . . . . ? 
 O2 C14 C15 F2 3.7(4) . . . . ? 
 C13 C14 C15 F2 -179.8(3) . . . . ? 
 O2 C14 C15 F1 -176.1(2) . . . . ? 
 C13 C14 C15 F1 0.4(5) . . . . ? 
 C19 N1 C16 O3 -177.8(3) . . . . ? 
 C17 N1 C16 O3 -2.1(5) . . . . ? 
 C19 N1 C16 O2 4.2(5) . . . . ? 
 C17 N1 C16 O2 179.9(3) . . . . ? 
 C14 O2 C16 O3 7.7(4) . . . . ? 
 C14 O2 C16 N1 -174.2(3) . . . . ? 
 C16 N1 C17 C18 -89.6(4) . . . . ? 
 C19 N1 C17 C18 86.3(4) . . . . ? 
 C16 N1 C19 C20 80.3(5) . . . . ? 
 C17 N1 C19 C20 -95.3(4) . . . . ? 
 
_refine_diff_density_max    0.228 
_refine_diff_density_min   -0.176 
_refine_diff_density_rms    0.051 




data_6E
 
_audit_creation_method            SHELXL
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C17 H22 F2 N2 O6'
_chemical_formula_weight          388.37
_chemical_melting_point           ?
_chemical_compound_source         ?
 
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'
 'F'  'F'   0.0171   0.0103
 '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                    7.7241(3)
_cell_length_b                    25.4363(8)
_cell_length_c                    10.1058(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  103.0745(16)
_cell_angle_gamma                 90.00
_cell_volume                      1934.04(12)
_cell_formula_units_Z             4
_cell_measurement_temperature     423(2)
_cell_measurement_reflns_used     na
_cell_measurement_theta_min       na
_cell_measurement_theta_max       na
 
_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_diffrn     1.334
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              816
_exptl_absorpt_coefficient_mu     0.113
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       423(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device        'Enraf Nonius KCCD area detector'
_diffrn_measurement_method        'Phi and Omega scans to fill Ewald sphere'
_diffrn_standards_number          'not measured'
_diffrn_standards_interval_count  na
_diffrn_standards_interval_time   na
_diffrn_standards_decay_%         na
_diffrn_reflns_number             24046
_diffrn_reflns_av_R_equivalents   0.0556
_diffrn_reflns_av_sigmaI/netI     0.0416
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -30
_diffrn_reflns_limit_k_max        30
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          3.01
_diffrn_reflns_theta_max          26.39
_reflns_number_total              3911
_reflns_number_observed           3035
_reflns_observed_criterion        >2sigma(I)
 
_computing_data_collection
;
DENZO (Otwinowski and MInor, 1997), COLLECT (Hooft, 1998)
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-96 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-96 (Sheldrick, 1996)'
_computing_molecular_graphics     ORTEP
_computing_publication_material   CIFTAB
 
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  Weighted R-factors wR and all
 goodnesses 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 observed criterion
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+1.4434P] 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     refine
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0068(17)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          3911
_refine_ls_number_parameters      252
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0763
_refine_ls_R_factor_obs           0.0570
_refine_ls_wR_factor_all          0.1512
_refine_ls_wR_factor_obs          0.1401
_refine_ls_goodness_of_fit_all    1.021
_refine_ls_goodness_of_fit_obs    1.082
_refine_ls_restrained_S_all       1.021
_refine_ls_restrained_S_obs       1.082
_refine_ls_shift/esd_max          0.000
_refine_ls_shift/esd_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_thermal_displace_type
 _atom_site_occupancy
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_group
F1 F 0.43455(16) 0.04306(5) 0.69517(16) 0.0448(4) Uani 1 d . .
O2 O 0.30541(18) -0.12215(6) 0.74090(16) 0.0324(4) Uani 1 d . .
O4 O 0.8505(2) -0.02029(6) 0.80209(18) 0.0382(4) Uani 1 d . .
F2 F 0.56582(19) 0.01365(5) 0.89451(13) 0.0456(4) Uani 1 d . .
O3 O 0.4819(2) -0.06000(6) 0.59767(16) 0.0397(4) Uani 1 d . .
O1 O 0.1012(2) -0.05796(6) 0.6785(2) 0.0484(5) Uani 1 d . .
N2 N 0.9647(3) 0.22924(8) 0.8839(2) 0.0444(5) Uani 1 d . .
N1 N 0.0419(2) -0.14315(8) 0.6100(2) 0.0430(5) Uani 1 d . .
C13 C 0.7379(3) 0.11629(8) 0.6842(2) 0.0301(5) Uani 1 d . .
H13 H 0.6622 0.1099 0.6001 0.036 Uiso 1 calc R .
C14 C 0.7889(3) 0.16709(8) 0.7212(2) 0.0325(5) Uani 1 d . .
H14 H 0.7481 0.1951 0.6634 0.039 Uiso 1 calc R .
C11 C 0.7380(3) 0.01876(8) 0.7293(2) 0.0277(4) Uani 1 d . .
H11 H 0.7305 0.0144 0.6318 0.033 Uiso 1 calc R .
C9 C 0.4850(3) -0.04725(8) 0.7129(2) 0.0281(5) Uani 1 d . .
C15 C 0.9025(3) 0.17540(8) 0.8466(2) 0.0333(5) Uani 1 d . .
C17 C 0.9108(3) 0.08403(9) 0.8974(2) 0.0328(5) Uani 1 d . .
H17 H 0.9508 0.0563 0.9564 0.039 Uiso 1 calc R .
C12 C 0.7984(3) 0.07419(8) 0.7714(2) 0.0267(4) Uani 1 d . .
C16 C 0.9633(3) 0.13482(9) 0.9354(2) 0.0353(5) Uani 1 d . .
H16 H 1.0385 0.1415 1.0195 0.042 Uiso 1 calc R .
C10 C 0.5568(3) 0.00745(8) 0.7597(2) 0.0299(5) Uani 1 d . .
C6 C 0.4234(3) -0.08296(8) 0.8135(2) 0.0292(5) Uani 1 d . .
H6 H 0.3630 -0.0623 0.8715 0.035 Uiso 1 calc R .
C5 C 0.1428(3) -0.10432(9) 0.6751(2) 0.0354(5) Uani 1 d . .
O6 O 1.0711(3) 0.23567(8) 0.9929(2) 0.0679(6) Uani 1 d . .
C7 C 0.5810(3) -0.11216(9) 0.9002(2) 0.0354(5) Uani 1 d . .
H7A H 0.6684 -0.0868 0.9452 0.043 Uiso 1 calc R .
H7B H 0.6360 -0.1336 0.8416 0.043 Uiso 1 calc R .
O5 O 0.9123(3) 0.26480(8) 0.8036(3) 0.0739(7) Uani 1 d . .
C4 C 0.1053(3) -0.19745(9) 0.6126(3) 0.0419(6) Uani 1 d . .
H4A H 0.2302 -0.1973 0.6104 0.050 Uiso 1 calc R .
H4B H 0.0409 -0.2156 0.5320 0.050 Uiso 1 calc R .
C8 C 0.5288(4) -0.14732(10) 1.0072(3) 0.0488(6) Uani 1 d . .
H8A H 0.6335 -0.1632 1.0621 0.073 Uiso 1 calc R .
H8B H 0.4495 -0.1743 0.9631 0.073 Uiso 1 calc R .
H8C H 0.4707 -0.1266 1.0637 0.073 Uiso 1 calc R .
C2 C -0.1472(3) -0.13358(12) 0.5476(4) 0.0651(9) Uani 1 d . .
H2A H -0.2190 -0.1588 0.5834 0.078 Uiso 1 calc R .
H2B H -0.1792 -0.0987 0.5726 0.078 Uiso 1 calc R .
C3 C 0.0818(5) -0.22689(12) 0.7370(3) 0.0641(8) Uani 1 d . .
H3A H 0.1504 -0.2101 0.8169 0.096 Uiso 1 calc R .
H3B H 0.1215 -0.2625 0.7330 0.096 Uiso 1 calc R .
H3C H -0.0415 -0.2268 0.7401 0.096 Uiso 1 calc R .
C1 C -0.1874(5) -0.13777(17) 0.3999(4) 0.0859(12) Uani 1 d . .
H1A H -0.1304 -0.1096 0.3630 0.129 Uiso 1 calc R .
H1B H -0.3137 -0.1356 0.3653 0.129 Uiso 1 calc R .
H1C H -0.1448 -0.1708 0.3743 0.129 Uiso 1 calc R .
H18 H 0.9199(46) -0.0271(13) 0.7591(34) 0.064(11) Uiso 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
F1 0.0295(7) 0.0311(7) 0.0740(11) 0.0048(7) 0.0124(6) 0.0054(5)
O2 0.0251(7) 0.0265(8) 0.0437(9) -0.0030(6) 0.0038(6) -0.0011(6)
O4 0.0352(9) 0.0309(9) 0.0465(10) 0.0042(7) 0.0047(8) 0.0077(7)
F2 0.0628(9) 0.0438(8) 0.0366(8) -0.0140(6) 0.0247(7) -0.0198(7)
O3 0.0470(9) 0.0412(9) 0.0294(9) -0.0057(7) 0.0057(7) -0.0077(7)
O1 0.0297(8) 0.0331(9) 0.0774(13) -0.0125(8) 0.0017(8) 0.0062(7)
N2 0.0401(11) 0.0362(12) 0.0602(14) -0.0122(11) 0.0182(10) -0.0129(9)
N1 0.0242(9) 0.0356(11) 0.0661(14) -0.0158(10) 0.0040(9) 0.0019(8)
C13 0.0286(10) 0.0321(11) 0.0281(11) 0.0005(9) 0.0031(8) -0.0004(9)
C14 0.0301(11) 0.0282(11) 0.0387(12) 0.0030(9) 0.0070(9) 0.0013(9)
C11 0.0270(10) 0.0267(11) 0.0284(11) -0.0001(8) 0.0042(8) 0.0019(8)
C9 0.0221(9) 0.0300(11) 0.0300(12) -0.0010(9) 0.0013(8) 0.0018(8)
C15 0.0272(10) 0.0295(11) 0.0441(13) -0.0079(10) 0.0098(9) -0.0059(9)
C17 0.0274(10) 0.0364(12) 0.0318(12) 0.0021(9) 0.0007(9) 0.0005(9)
C12 0.0223(9) 0.0284(11) 0.0295(11) -0.0004(8) 0.0058(8) 0.0009(8)
C16 0.0250(10) 0.0429(13) 0.0345(12) -0.0058(10) -0.0003(9) -0.0038(9)
C10 0.0323(11) 0.0288(11) 0.0298(11) -0.0007(9) 0.0092(9) 0.0019(9)
C6 0.0281(10) 0.0260(10) 0.0327(12) -0.0030(8) 0.0051(9) -0.0031(8)
C5 0.0240(10) 0.0319(12) 0.0506(14) -0.0079(10) 0.0087(10) 0.0016(9)
O6 0.0867(15) 0.0639(13) 0.0525(12) -0.0193(10) 0.0143(11) -0.0429(12)
C7 0.0318(11) 0.0345(12) 0.0372(13) 0.0039(10) 0.0020(9) -0.0005(9)
O5 0.0670(14) 0.0295(10) 0.112(2) 0.0001(11) -0.0065(13) -0.0072(9)
C4 0.0373(12) 0.0334(13) 0.0533(15) -0.0138(11) 0.0069(11) -0.0018(10)
C8 0.0492(15) 0.0452(15) 0.0498(16) 0.0145(12) 0.0065(12) 0.0038(12)
C2 0.0293(13) 0.0574(18) 0.101(3) -0.0269(17) -0.0005(14) 0.0027(12)
C3 0.075(2) 0.0479(17) 0.072(2) -0.0067(15) 0.0217(17) -0.0177(15)
C1 0.060(2) 0.095(3) 0.095(3) 0.001(2) 0.0010(19) 0.0270(19)
 
_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
F1 C10 1.3635(25) . ?
O2 C5 1.3593(25) . ?
O2 C6 1.4353(25) . ?
O4 C11 1.4122(25) . ?
F2 C10 1.3575(24) . ?
O3 C9 1.2036(25) . ?
O1 C5 1.2246(27) . ?
N2 O5 1.2214(30) . ?
N2 O6 1.2276(30) . ?
N2 C15 1.4717(29) . ?
N1 C5 1.3357(29) . ?
N1 C4 1.4636(30) . ?
N1 C2 1.4739(31) . ?
C13 C14 1.3777(30) . ?
C13 C12 1.3983(29) . ?
C14 C15 1.3850(32) . ?
C11 C12 1.5153(28) . ?
C11 C10 1.5263(28) . ?
C9 C6 1.5179(29) . ?
C9 C10 1.5328(29) . ?
C15 C16 1.3786(33) . ?
C17 C16 1.3821(32) . ?
C17 C12 1.3926(30) . ?
C6 C7 1.5230(29) . ?
C7 C8 1.5259(33) . ?
C4 C3 1.5091(40) . ?
C2 C1 1.4576(52) . ?
 
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
C5 O2 C6 115.33(16) . . ?
O5 N2 O6 123.5(2) . . ?
O5 N2 C15 118.6(2) . . ?
O6 N2 C15 117.8(2) . . ?
C5 N1 C4 122.23(19) . . ?
C5 N1 C2 120.0(2) . . ?
C4 N1 C2 117.3(2) . . ?
C14 C13 C12 120.9(2) . . ?
C13 C14 C15 118.4(2) . . ?
O4 C11 C12 113.21(17) . . ?
O4 C11 C10 104.28(17) . . ?
C12 C11 C10 110.91(16) . . ?
O3 C9 C6 123.10(19) . . ?
O3 C9 C10 118.02(19) . . ?
C6 C9 C10 118.87(18) . . ?
C16 C15 C14 122.2(2) . . ?
C16 C15 N2 119.1(2) . . ?
C14 C15 N2 118.6(2) . . ?
C16 C17 C12 120.3(2) . . ?
C17 C12 C13 119.28(19) . . ?
C17 C12 C11 120.84(19) . . ?
C13 C12 C11 119.86(18) . . ?
C15 C16 C17 118.9(2) . . ?
F2 C10 F1 105.99(17) . . ?
F2 C10 C11 109.82(17) . . ?
F1 C10 C11 110.24(17) . . ?
F2 C10 C9 110.37(17) . . ?
F1 C10 C9 106.99(16) . . ?
C11 C10 C9 113.15(17) . . ?
O2 C6 C9 109.41(17) . . ?
O2 C6 C7 106.73(17) . . ?
C9 C6 C7 110.25(17) . . ?
O1 C5 N1 126.8(2) . . ?
O1 C5 O2 121.8(2) . . ?
N1 C5 O2 111.46(18) . . ?
C6 C7 C8 112.86(19) . . ?
N1 C4 C3 112.4(2) . . ?
C1 C2 N1 112.8(3) . . ?
 
_refine_diff_density_max    0.834
_refine_diff_density_min   -0.347
_refine_diff_density_rms    0.050