# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1278 #============================================================================ data_ni200 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H20 F6 N2 O2' _chemical_formula_weight 386.34 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0015 0.0009 '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' 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0096 0.0061 '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 5.849(2) _cell_length_b 31.360(200) _cell_length_c 9.436(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.8600(5) _cell_angle_gamma 90.00 _cell_volume 1726.9(111) _cell_formula_units_Z 4 _cell_measurement_temperature 50(2) _cell_measurement_reflns_used 14483 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 25.13 _exptl_crystal_description platy _exptl_crystal_colour orange _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method ? _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 50(2) _diffrn_radiation_wavelength 0.56080 _diffrn_radiation_type AgK\a _diffrn_radiation_source 'rotating anode generator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'MarResearch image-plate detector' _diffrn_measurement_method 'phi scans' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 21072 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 47 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.13 _reflns_number_total 6049 _reflns_number_observed 5018 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'MARVIEW' _computing_cell_refinement 'MARXDS 2.1 (Klein, 1994)' _computing_data_reduction 'MARXDS 2.1 (Klein, 1994)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 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. MARXDS set all negative F^2^ to zero during data reduction. These data were included in refinement. ; _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^)+(0.0513P)^2^+0.7519P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6049 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.001 _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 0.58067(18) 0.14494(3) 0.70218(10) 0.00677(17) Uani 1 1 d . . . H1A H 0.6159 0.1661 0.6333 0.013(3) Uiso 1 1 d R . . C2 C 0.43888(18) 0.15556(3) 0.81011(10) 0.00594(16) Uani 1 1 d . . . C3 C 0.38444(18) 0.12422(3) 0.90914(10) 0.00732(17) Uani 1 1 d . . . C4 C 0.4806(2) 0.08386(3) 0.90130(11) 0.00962(19) Uani 1 1 d . . . H4A H 0.4460 0.0627 0.9701 0.013(3) Uiso 1 1 d R . . C5 C 0.62604(19) 0.07349(3) 0.79527(11) 0.00861(18) Uani 1 1 d . . . C6 C 0.67101(18) 0.10404(3) 0.69257(10) 0.00676(17) Uani 1 1 d . . . C7 C 0.24388(18) 0.22532(3) 0.71048(10) 0.00610(17) Uani 1 1 d . . . C8 C 0.21209(19) 0.13159(3) 1.01944(10) 0.00902(18) Uani 1 1 d . . . C9 C 0.7250(2) 0.02911(4) 0.79215(11) 0.0117(2) Uani 1 1 d . . . C10 C 0.73356(18) 0.09173(3) 0.42631(10) 0.00745(17) Uani 1 1 d . . . C11 C 0.1596(2) 0.19759(4) 0.58414(11) 0.01031(19) Uani 1 1 d . . . H11A H 0.2887 0.1850 0.5425 0.0208(11) Uiso 1 1 d R . . H11B H 0.0616 0.1755 0.6160 0.0208(11) Uiso 1 1 d R . . H11C H 0.0757 0.2149 0.5146 0.0208(11) Uiso 1 1 d R . . C12 C 0.4085(2) 0.26001(3) 0.66665(11) 0.00984(18) Uani 1 1 d . . . H12A H 0.5370 0.2471 0.6252 0.0208(11) Uiso 1 1 d R . . H12B H 0.3304 0.2786 0.5985 0.0208(11) Uiso 1 1 d R . . H12C H 0.4615 0.2762 0.7487 0.0208(11) Uiso 1 1 d R . . C13 C 0.03772(19) 0.24555(4) 0.77694(11) 0.01016(19) Uani 1 1 d . . . H13A H 0.0904 0.2630 0.8562 0.0208(11) Uiso 1 1 d R . . H13B H -0.0461 0.2628 0.7074 0.0208(11) Uiso 1 1 d R . . H13C H -0.0602 0.2235 0.8088 0.0208(11) Uiso 1 1 d R . . C14 C 0.8046(2) 0.13235(4) 0.35055(11) 0.01096(19) Uani 1 1 d . . . H14A H 0.7321 0.1566 0.3906 0.0208(11) Uiso 1 1 d R . . H14B H 0.9680 0.1356 0.3623 0.0208(11) Uiso 1 1 d R . . H14C H 0.7582 0.1303 0.2512 0.0208(11) Uiso 1 1 d R . . C15 C 0.47385(19) 0.08648(4) 0.41613(11) 0.01035(19) Uani 1 1 d . . . H15A H 0.4044 0.1111 0.4561 0.0208(11) Uiso 1 1 d R . . H15B H 0.4198 0.0836 0.3183 0.0208(11) Uiso 1 1 d R . . H15C H 0.4339 0.0615 0.4676 0.0208(11) Uiso 1 1 d R . . C16 C 0.8483(2) 0.05286(4) 0.36306(12) 0.0120(2) Uani 1 1 d . . . H16A H 0.8031 0.0275 0.4110 0.0208(11) Uiso 1 1 d R . . H16B H 0.8019 0.0507 0.2638 0.0208(11) Uiso 1 1 d R . . H16C H 1.0117 0.0560 0.3748 0.0208(11) Uiso 1 1 d R . . N1 N 0.36519(16) 0.19849(3) 0.82437(9) 0.00626(15) Uani 1 1 d . . . N2 N 0.81742(16) 0.09475(3) 0.58032(9) 0.00692(16) Uani 1 1 d . . . O1 O 0.40391(15) 0.21519(3) 0.94817(8) 0.01036(15) Uani 1 1 d . . . O2 O 1.03148(14) 0.09026(3) 0.61623(9) 0.01332(17) Uani 1 1 d . . . F1 F 0.03282(12) 0.15496(2) 0.96846(7) 0.01187(14) Uani 1 1 d . . . F2 F 0.30115(14) 0.15099(2) 1.13768(7) 0.01331(14) Uani 1 1 d . . . F3 F 0.12606(14) 0.09432(2) 1.06249(7) 0.01410(15) Uani 1 1 d . . . F4 F 0.70706(15) 0.01216(2) 0.66126(8) 0.01698(16) Uani 1 1 d . . . F5 F 0.94644(15) 0.02782(3) 0.83722(9) 0.02093(17) Uani 1 1 d . . . F6 F 0.61481(17) 0.00227(2) 0.87535(9) 0.02164(19) 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 0.0074(4) 0.0060(4) 0.0071(4) 0.0002(3) 0.0019(3) 0.0000(3) C2 0.0066(4) 0.0053(4) 0.0060(4) -0.0002(3) 0.0008(3) 0.0003(3) C3 0.0088(4) 0.0069(4) 0.0065(4) 0.0008(3) 0.0027(3) 0.0010(3) C4 0.0131(5) 0.0072(4) 0.0091(4) 0.0019(3) 0.0042(3) 0.0013(4) C5 0.0116(5) 0.0055(4) 0.0092(4) 0.0011(3) 0.0039(3) 0.0021(3) C6 0.0069(4) 0.0062(4) 0.0074(4) -0.0004(3) 0.0022(3) 0.0008(3) C7 0.0078(4) 0.0055(4) 0.0050(3) 0.0003(3) 0.0006(3) 0.0012(3) C8 0.0116(5) 0.0076(4) 0.0083(4) 0.0009(3) 0.0041(3) 0.0005(4) C9 0.0166(5) 0.0071(4) 0.0120(4) 0.0021(3) 0.0064(4) 0.0031(4) C10 0.0072(4) 0.0083(4) 0.0072(4) -0.0016(3) 0.0022(3) -0.0007(3) C11 0.0135(5) 0.0088(4) 0.0083(4) -0.0011(3) -0.0024(3) 0.0011(4) C12 0.0122(5) 0.0087(4) 0.0088(4) 0.0015(3) 0.0021(3) -0.0019(4) C13 0.0098(4) 0.0116(5) 0.0094(4) 0.0014(3) 0.0024(3) 0.0032(4) C14 0.0127(5) 0.0113(4) 0.0092(4) 0.0007(3) 0.0028(3) -0.0017(4) C15 0.0071(4) 0.0132(5) 0.0110(4) -0.0018(3) 0.0018(3) -0.0003(4) C16 0.0120(5) 0.0114(5) 0.0129(4) -0.0042(3) 0.0037(4) 0.0011(4) N1 0.0088(4) 0.0049(3) 0.0051(3) -0.0005(3) 0.0003(3) 0.0013(3) N2 0.0060(4) 0.0076(4) 0.0075(3) -0.0006(3) 0.0025(3) 0.0007(3) O1 0.0162(4) 0.0089(3) 0.0057(3) -0.0031(2) -0.0014(3) 0.0004(3) O2 0.0053(3) 0.0217(4) 0.0129(3) 0.0001(3) 0.0006(3) 0.0022(3) F1 0.0101(3) 0.0131(3) 0.0130(3) 0.0011(2) 0.0045(2) 0.0037(3) F2 0.0200(4) 0.0137(3) 0.0066(3) -0.0015(2) 0.0035(2) 0.0005(3) F3 0.0194(4) 0.0091(3) 0.0152(3) 0.0022(2) 0.0112(3) -0.0011(3) F4 0.0288(4) 0.0081(3) 0.0147(3) -0.0027(2) 0.0064(3) 0.0040(3) F5 0.0183(4) 0.0150(4) 0.0292(4) 0.0011(3) -0.0001(3) 0.0099(3) F6 0.0340(5) 0.0084(3) 0.0250(4) 0.0079(3) 0.0197(3) 0.0063(3) _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. Geometry of methyl groups was constrained to tetrahedral angles with d(C-H) = 0.96A. Geometry of H external to aromatic ring was constrained such that C-H bisects the external C-C-C angle and d(C-H) = 0.96A. A single isotropic ADP was refined for each of these two hydrogen types. Mean plane fit to C1 through C6 fits these to RMS deviation of 0.014A. Other distances to this plane: C8 0.158(2)A C7 0.034(2)A N2 0.020(2)A N1 0.153(2)A N1 is 0.009(1)A from plane defined by C2, C7, O1 N2 is 0.016(1)A from plane defined by C6, C10, O2 Torsion angle C5-C6-N2-O2 -69.65(17)degrees Torsion angle C3-C2-N1-O1 48.77(14)degrees ; 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 C6 1.392(8) . yes C1 C2 1.3963(15) . yes C2 C3 1.407(5) . yes C2 N1 1.423(8) . yes C3 C4 1.389(8) . yes C3 C8 1.5146(16) . yes C4 C5 1.3946(16) . yes C5 C6 1.400(4) . yes C5 C9 1.509(8) . yes C6 N2 1.4361(14) . yes C7 N1 1.505(3) . yes C7 C12 1.528(5) . yes C7 C11 1.530(4) . yes C7 C13 1.533(2) . yes C8 F1 1.342(3) . yes C8 F2 1.345(2) . yes C8 F3 1.346(7) . yes C9 F5 1.3362(15) . yes C9 F4 1.342(2) . yes C9 F6 1.345(4) . yes C10 N2 1.5051(16) . yes C10 C15 1.5245(16) . yes C10 C14 1.532(7) . yes C10 C16 1.532(6) . yes N1 O1 1.2863(19) . yes N2 O2 1.2826(13) . yes 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 C6 C1 C2 120.91(9) . . yes C1 C2 C3 119.3(3) . . yes C1 C2 N1 119.55(9) . . yes C3 C2 N1 121.0(3) . . yes C4 C3 C2 119.4(3) . . yes C4 C3 C8 117.78(10) . . yes C2 C3 C8 122.7(2) . . yes C3 C4 C5 121.28(10) . . yes C4 C5 C6 119.3(3) . . yes C4 C5 C9 118.85(9) . . yes C6 C5 C9 121.8(3) . . yes C1 C6 C5 119.7(3) . . yes C1 C6 N2 118.85(9) . . yes C5 C6 N2 121.4(3) . . yes N1 C7 C12 108.4(2) . . yes N1 C7 C11 110.5(3) . . yes C12 C7 C11 111.7(2) . . yes N1 C7 C13 106.57(15) . . yes C12 C7 C13 110.1(3) . . yes C11 C7 C13 109.44(15) . . yes F1 C8 F2 107.5(3) . . yes F1 C8 F3 106.5(3) . . yes F2 C8 F3 105.9(2) . . yes F1 C8 C3 112.16(9) . . yes F2 C8 C3 113.62(10) . . yes F3 C8 C3 110.8(2) . . yes F5 C9 F4 107.17(10) . . yes F5 C9 F6 106.72(11) . . yes F4 C9 F6 106.2(3) . . yes F5 C9 C5 112.76(15) . . yes F4 C9 C5 112.14(17) . . yes F6 C9 C5 111.5(3) . . yes N2 C10 C15 109.04(8) . . yes N2 C10 C14 108.50(15) . . yes C15 C10 C14 111.15(9) . . yes N2 C10 C16 107.67(9) . . yes C15 C10 C16 110.50(18) . . yes C14 C10 C16 109.9(4) . . yes O1 N1 C2 115.80(15) . . yes O1 N1 C7 117.8(3) . . yes C2 N1 C7 126.36(18) . . yes O2 N2 C6 116.58(9) . . yes O2 N2 C10 119.81(8) . . yes C6 N2 C10 123.58(9) . . yes _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 25.13 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.507 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.058