# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name 'Jan Bergman' 'Ivan Romero' 'Per Wiklund' _publ_contact_author_name 'Prof Jan Bergman' _publ_contact_author_address ; Department of Biosciences Unit for Organic Chemistry Karolinska Institute and Sodertorn Novum Reserach Park Huddinge 141 57 Huddinge SWEDEN ; _publ_contact_author_email JAN.BERGMAN@BIOSCI.KI.SE _publ_section_title ; Products from dehydration of dicarboxylic acids derived from anthranilic acid ; _publ_section_abstract ; Structure,Packing 3a-Pentafluoroethyl-3,4-dioxa-9b-aza-benz[e]indene-2,5-dione ; _publ_section_comment ; The single-crystal X-ray study of the titled compound was undertaken to establish its three dimensional crystal structure. Geometries are tabulated below. All Diagrams and calculations were performed using maXus (Nonius, Delft & MacScience, Japan). ; _publ_section_references ; Nonius B.V. (2000). KappaCCD Server Software. Nonius, B.V., Delft, The Nederlands. Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Hooft, R. (1998). Collect. Software for data collection and unit-cell determination. Nonius, B.V.,Delft, The Netherlands. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). SIR92. J. Appl. Cryst. 27, 435. Waasmaier, D. & Kirfel, A. (1995). Acta Cryst. A51, 416-431. Spek, A. L. (1999). Platon. A program designed for generation and analysis of stereochemical and molecular geometry data. University of Utrecht, Netherlands. Hall, S. R. Allen, F. H.& Brown, I. D. (1991). CIF. Crystallographic Information File for Crystallographic Data Exchange. Acta Cryst. A47, 665-685. ; data_3a-Pentafluoroethyl-3,4-dioxa-9b-aza-benz[e]indene-2,5-dione _database_code_CSD 212237 _chemical_name_common ;(()3a-Pentafluoroethyl-3,4-dioxa-9b-aza- cyclopenta(a)naphthalene-2,5-dione ; #============================================================= _audit_creation_method maXus #------------------------------------------------------------------------------- _chemical_compound_source ; Per Wiklund: Organic Chemistry CNT Biosciences, Karolinska Institute, Novum 141 57 Huddinge, Sweden ; _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 loop_ _diffrn_radiation_wavelength 0.71073 _exptl_crystal_size_min 0.11 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_max 0.23 _exptl_crystal_description rod _exptl_crystal_colour Colourless _cell_measurement_temperature 298 _refine_ls_hydrogen_treatment refxyz _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 323.173 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z '-X,+Y+ 1/2,-Z+ 1/2' '+X,-Y+ 1/2,+Z+ 1/2' _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_cell_setting Monoclinic _chemical_formula_moiety 'C12 H6 F5 N O4 ' _chemical_formula_sum 'C12 H6 F5 N O4 ' _chemical_name_systematic ; (()3a-Pentafluoroethyl-3,4-dioxa-9b-aza-cyclopenta[a]naphthalene-2,5-dione ; _cell_length_a 10.323(1) _cell_length_b 8.328(1) _cell_length_c 15.665(1) _cell_angle_alpha 90(1) _cell_angle_beta 108.30(1) _cell_angle_gamma 90(1) _cell_volume 1278.6(2) _diffrn_reflns_number 5003 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_av_R_equivalents 0.029 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_coefficient_mu 0.17 _exptl_crystal_F_000 648 #------------------------------------------------------------------------------- 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 'Waasmaier & Kirfel, 1995' 'H ' 'H ' 0.0000 0.0000 'Waasmaier & Kirfel, 1995' 'F ' 'F ' 0.0171 0.0103 'Waasmaier & Kirfel, 1995' 'O ' 'O ' 0.0106 0.0060 'Waasmaier & Kirfel, 1995' 'N ' 'N ' 0.0061 0.0033 'Waasmaier & Kirfel, 1995' _reflns_number_total 2851 _reflns_number_gt 1148 _reflns_threshold_expression 'I> 4.00 sigma(I)' _reflns_d_resolution_low 1.93 _reflns_d_resolution_high 0.63 _reflns_limit_h_max 13 _reflns_limit_h_min 0 _reflns_limit_k_max 10 _reflns_limit_k_min 0 _reflns_limit_l_max 13 _reflns_limit_l_min -4 _refine_ls_matrix_type full _refine_ls_R_factor_all 0.138 _refine_ls_wR_factor_all 0.172 _refine_ls_R_factor_gt 0.050 _refine_ls_wR_factor_gt 0.060 _refine_ls_wR_factor_ref 0.060 _refine_ls_goodness_of_fit_gt 1.554 _refine_ls_goodness_of_fit_ref 1.554 _refine_ls_goodness_of_fit_all 2.455 _refine_ls_number_parameters 200 _refine_ls_number_reflns 1148 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ; w = 1 / ( s^2^(Fo^2^) + 0.03000 * Fo^2^) ; _refine_ls_extinction_method Zachariasen _refine_ls_extinction_expression ? _refine_ls_extinction_coef 16267(1410) _computing_structure_refinement 'maxus(Mackay et al., 1999)' _computing_molecular_graphics 'Ortep (Johnson, 1976)' _computing_publication_material 'maxus(Mackay et al., 1999)' _atom_sites_solution_hydrogens geom _refine_diff_density_max 0.40 _refine_diff_density_min -0.31 _refine_diff_density_rms 0.05 #=============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type F16 0.4351(2) 0.1109(2) 0.4307(1) 0.106(1) 1.00 Uij F17 0.2541(2) -0.0333(2) 0.3717(2) 0.126(2) 1.00 Uij F18 0.4454(3) 0.1514(3) 0.2582(2) 0.225(3) 1.00 Uij F19 0.4650(3) -0.0806(3) 0.3056(2) 0.183(2) 1.00 Uij F20 0.2850(4) -0.0075(4) 0.2125(2) 0.192(3) 1.00 Uij O3 0.4067(2) 0.5949(3) 0.4111(2) 0.086(1) 1.00 Uij O4 0.3185(2) 0.3725(2) 0.3349(1) 0.060(1) 1.00 Uij O6 0.1307(2) 0.2268(2) 0.2634(1) 0.059(1) 1.00 Uij O7 -0.0646(2) 0.1115(3) 0.1912(1) 0.078(1) 1.00 Uij N1 0.1975(2) 0.2726(2) 0.4219(1) 0.049(1) 1.00 Uij C2 0.2674(3) 0.4148(3) 0.4680(2) 0.060(2) 1.00 Uij C3 0.3399(3) 0.4782(4) 0.4066(2) 0.062(2) 1.00 Uij C5 0.2372(3) 0.2423(3) 0.3442(2) 0.051(2) 1.00 Uij C7 0.0071(3) 0.1596(3) 0.2628(2) 0.058(2) 1.00 Uij C8 -0.0243(3) 0.1641(3) 0.3469(2) 0.045(1) 1.00 Uij C9 -0.1520(3) 0.1143(3) 0.3490(2) 0.062(2) 1.00 Uij C10 -0.1872(3) 0.1304(3) 0.4257(2) 0.069(2) 1.00 Uij C11 -0.0956(3) 0.1979(3) 0.5005(2) 0.065(2) 1.00 Uij C12 0.0315(3) 0.2474(3) 0.5010(2) 0.055(2) 1.00 Uij C13 0.0684(3) 0.2293(3) 0.4235(2) 0.046(2) 1.00 Uij C14 0.3267(3) 0.0903(3) 0.3569(2) 0.070(2) 1.00 Uij C15 0.3849(5) 0.0435(5) 0.2825(3) 0.102(3) 1.00 Uij H9 -0.2157(2) 0.0680(3) 0.2963(1) 0.050(1) 1.00 Uiso H10 -0.2750(2) 0.0950(2) 0.4271(1) 0.050(1) 1.00 Uiso H11 -0.1198(2) 0.2114(2) 0.5545(2) 0.050(2) 1.00 Uiso H12 0.0956(3) 0.2945(3) 0.5532(2) 0.050(4) 1.00 Uiso H2A 0.3335(3) 0.3904(3) 0.5250(2) 0.050(3) 1.00 Uiso H2B 0.2059(4) 0.4956(4) 0.4760(2) 0.050(3) 1.00 Uiso #------------------------------------------------------------------------------- loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F16 0.091(1) 0.113(2) 0.097(2) 0.049(1) 0.014(1) 0.023(1) F17 0.137(2) 0.053(1) 0.193(2) 0.014(1) 0.118(2) 0.033(1) F18 0.311(4) 0.096(2) 0.297(4) -.022(2) 0.270(4) -.002(2) F19 0.200(3) 0.109(2) 0.244(3) 0.073(2) 0.152(3) 0.022(2) F20 0.175(3) 0.233(3) 0.159(3) 0.012(3) 0.076(2) -.097(3) O3 0.075(1) 0.068(1) 0.098(2) -.026(1) 0.005(1) 0.009(1) O4 0.054(1) 0.054(1) 0.065(1) -.0050(9) 0.021(1) 0.015(1) O6 0.058(1) 0.072(1) 0.042(1) -.009(1) 0.019(1) 0.0031(9) O7 0.077(1) 0.106(2) 0.041(1) -.026(1) 0.012(1) -.006(1) N1 0.044(1) 0.054(1) 0.043(1) -.006(1) 0.011(1) -.002(1) C2 0.048(2) 0.067(2) 0.054(2) -.006(1) 0.000(1) -.006(2) C3 0.052(2) 0.057(2) 0.066(2) -.001(2) 0.001(2) 0.008(2) C5 0.047(2) 0.050(2) 0.051(2) -.004(1) 0.018(2) 0.009(1) C7 0.059(2) 0.061(2) 0.046(2) -.009(2) 0.016(2) 0.002(2) C8 0.045(2) 0.049(2) 0.037(2) -.005(1) 0.013(1) 0.002(1) C9 0.056(2) 0.065(2) 0.058(2) -.016(2) 0.017(2) -.007(2) C10 0.055(2) 0.075(2) 0.073(2) -.014(2) 0.031(2) -.005(2) C11 0.075(2) 0.058(2) 0.061(2) -.003(2) 0.039(2) -.003(2) C12 0.059(2) 0.054(2) 0.046(2) -.004(1) 0.017(2) -.005(1) C13 0.048(2) 0.042(1) 0.043(2) 0.000(1) 0.016(1) 0.003(1) C14 0.070(2) 0.054(2) 0.083(2) 0.002(2) 0.039(2) 0.011(2) C15 0.106(3) 0.074(3) 0.124(4) 0.000(2) 0.067(3) -.013(3) #------------------------------------------------------------------------------- _geom_special_details ; All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case. ; #------------------------------------------------------------------------------- loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F16 C14 1.344(4) . . ? F17 C14 1.336(3) . . ? F18 C15 1.221(4) . . ? F19 C15 1.302(4) . . ? F20 C15 1.318(5) . . ? O3 C3 1.181(3) . . ? O4 C3 1.390(3) . . ? O4 C5 1.406(3) . . ? O6 C5 1.397(3) . . ? O6 C7 1.390(3) . . ? O7 C7 1.202(3) . . ? N1 C2 1.456(3) . . ? N1 C5 1.424(3) . . ? N1 C13 1.388(3) . . ? C2 C3 1.489(4) . . ? C7 C8 1.452(4) . . ? C8 C9 1.393(3) . . ? C8 C13 1.389(3) . . ? C9 C10 1.366(4) . . ? C10 C11 1.374(4) . . ? C11 C12 1.374(4) . . ? C12 C13 1.389(3) . . ? C2 H2A 0.960(3) . . ? C2 H2B 0.960(3) . . ? C9 H9 0.960(3) . . ? C10 H10 0.960(3) . . ? C11 H11 0.960(3) . . ? C12 H12 0.960(3) . . ? #------------------------------------------------------------------------------- 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O4 C5 110.7(3) . . . ? C5 O6 C7 120.2(3) . . . ? C2 N1 C5 109.8(2) . . . ? C2 N1 C13 122.1(3) . . . ? C5 N1 C13 120.4(3) . . . ? N1 C2 C3 103.8(3) . . . ? O3 C3 O4 120.7(3) . . . ? O3 C3 C2 131.0(4) . . . ? O4 C3 C2 108.3(3) . . . ? O4 C5 O6 107.7(2) . . . ? O4 C5 N1 107.1(3) . . . ? O6 C5 N1 115.7(3) . . . ? O6 C7 O7 115.8(3) . . . ? O6 C7 C8 116.7(3) . . . ? O7 C7 C8 127.4(3) . . . ? C7 C8 C9 119.8(3) . . . ? C7 C8 C13 120.3(3) . . . ? C9 C8 C13 119.7(3) . . . ? C8 C9 C10 120.5(3) . . . ? C9 C10 C11 119.2(3) . . . ? C10 C11 C12 121.8(3) . . . ? C11 C12 C13 119.1(3) . . . ? N1 C13 C8 119.4(3) . . . ? N1 C13 C12 121.1(3) . . . ? C8 C13 C12 119.6(3) . . . ? F16 C14 F17 108.1(3) . . . ? F18 C15 F19 109.2(4) . . . ? F18 C15 F20 108.8(5) . . . ? F19 C15 F20 103.8(4) . . . ? N1 C2 H2A 112.7(3) . . . ? N1 C2 H2B 113.0(3) . . . ? C3 C2 H2A 108.7(3) . . . ? C3 C2 H2B 108.8(3) . . . ? H2A C2 H2B 109.5(3) . . . ? C8 C9 H9 119.7(3) . . . ? C10 C9 H9 119.8(3) . . . ? C9 C10 H10 120.2(4) . . . ? C11 C10 H10 120.5(3) . . . ? C10 C11 H11 120.0(3) . . . ? C12 C11 H11 118.2(4) . . . ? C11 C12 H12 121.9(3) . . . ? C13 C12 H12 119.0(3) . . . ? #------------------------------------------------------------------------------- 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 C5 O4 C3 O3 179.6(4) . . . . ? C3 O4 C5 O6 129.2(3) . . . . ? C3 O4 C5 N1 4.2(3) . . . . ? C5 O4 C3 C2 -0.3(3) . . . . ? C7 O6 C5 O4 -152.9(3) . . . . ? C5 O6 C7 O7 -160.9(4) . . . . ? C7 O6 C5 N1 -33.2(3) . . . . ? C5 O6 C7 C8 22.6(3) . . . . ? C2 N1 C5 O4 -6.5(2) . . . . ? C2 N1 C5 O6 -126.5(3) . . . . ? C5 N1 C2 C3 6.2(3) . . . . ? C13 N1 C2 C3 -143.0(4) . . . . ? C2 N1 C13 C8 142.6(4) . . . . ? C2 N1 C13 C12 -38.7(3) . . . . ? C13 N1 C5 O4 143.3(3) . . . . ? C13 N1 C5 O6 23.3(3) . . . . ? C5 N1 C13 C8 -3.4(3) . . . . ? C5 N1 C13 C12 175.3(4) . . . . ? N1 C2 C3 O3 176.6(5) . . . . ? N1 C2 C3 O4 -3.6(3) . . . . ? O6 C7 C8 C9 173.4(4) . . . . ? O6 C7 C8 C13 -1.6(3) . . . . ? O7 C7 C8 C9 -2.6(3) . . . . ? O7 C7 C8 C13 -177.6(5) . . . . ? C7 C8 C9 C10 -174.5(5) . . . . ? C7 C8 C13 N1 -7.6(3) . . . . ? C7 C8 C13 C12 173.6(4) . . . . ? C9 C8 C13 N1 177.4(4) . . . . ? C13 C8 C9 C10 0.6(3) . . . . ? C9 C8 C13 C12 -1.4(3) . . . . ? C8 C9 C10 C11 0.6(3) . . . . ? C9 C10 C11 C12 -1.0(3) . . . . ? C10 C11 C12 C13 0.2(3) . . . . ? C11 C12 C13 N1 -177.7(4) . . . . ? C11 C12 C13 C8 1.0(3) . . . . ? C5 N1 C2 H2A -111.3(4) . . . . ? C5 N1 C2 H2B 123.9(4) . . . . ? C13 N1 C2 H2A 99.5(4) . . . . ? C13 N1 C2 H2B -25.3(4) . . . . ? H2A C2 C3 O3 -63.1(5) . . . . ? H2A C2 C3 O4 116.7(4) . . . . ? H2B C2 C3 O3 56.0(5) . . . . ? H2B C2 C3 O4 -124.1(4) . . . . ? C7 C8 C9 H9 5.7(3) . . . . ? C13 C8 C9 H9 -179.2(5) . . . . ? C8 C9 C10 H10 -179.4(5) . . . . ? H9 C9 C10 C11 -179.6(5) . . . . ? H9 C9 C10 H10 0.4(4) . . . . ? C9 C10 C11 H11 179.0(5) . . . . ? H10 C10 C11 C12 179.0(6) . . . . ? H10 C10 C11 H11 -1.0(4) . . . . ? C10 C11 C12 H12 -180.0(6) . . . . ? H11 C11 C12 C13 -179.8(5) . . . . ? H11 C11 C12 H12 0.0(4) . . . . ? H12 C12 C13 N1 2.5(4) . . . . ? H12 C12 C13 C8 -178.8(5) . . . . ? #------------------------------------------------------------------------------- loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag F16 F16 2.845(4) 1_555 2_656 ? F17 C11 3.258(3) 1_555 2_556 ? F17 H11 2.542(2) 1_555 2_556 ? F18 F19 2.723(3) 1_555 3_655 ? F20 C9 3.450(5) 1_555 3_545 ? O3 C2 3.303(3) 1_555 2_666 ? O3 C3 3.267(4) 1_555 2_666 ? O3 H2A 2.554(2) 1_555 2_666 ? O4 C9 3.493(3) 1_555 3_555 ? O4 H9 2.575(2) 1_555 3_555 ? O7 C2 3.164(3) 1_555 3_545 ? O7 C3 2.987(3) 1_555 3_545 ? O7 C5 3.509(3) 1_555 3_545 ? O7 C11 3.309(4) 1_555 4_565 ? O7 H11 2.515(2) 1_555 4_565 ? C2 C11 3.787(4) 1_555 2_566 ? C3 C3 3.679(6) 1_555 2_666 ? C3 H9 3.123(3) 1_555 3_555 ? C8 C11 3.805(4) 1_555 2_556 ? C9 C11 3.881(4) 1_555 2_556 ? C9 C12 3.782(4) 1_555 2_556 ? C10 C11 3.900(4) 1_555 2_556 ? C10 C12 3.556(4) 1_555 2_556 ? C10 C13 3.774(4) 1_555 2_556 ? C11 C11 3.844(5) 1_555 2_556 ? C11 C12 3.768(4) 1_555 2_556 ? C11 C13 3.734(4) 1_555 2_556 ? C11 H2B 2.865(3) 1_555 2_566 ? F16 F16 2.845(4) 1_555 2_656 ? F17 C11 3.258(3) 1_555 2_556 ? F17 H11 2.542(2) 1_555 2_556 ? F18 F19 2.723(3) 1_555 3_655 ? F20 C9 3.450(5) 1_555 3_545 ? O3 C2 3.303(3) 1_555 2_666 ? O3 C3 3.267(4) 1_555 2_666 ? O3 H2A 2.554(2) 1_555 2_666 ? O4 C9 3.493(3) 1_555 3_555 ? O4 H9 2.575(2) 1_555 3_555 ? O7 C2 3.164(3) 1_555 3_545 ? O7 C3 2.987(3) 1_555 3_545 ? O7 C5 3.509(3) 1_555 3_545 ? O7 C11 3.309(4) 1_555 4_565 ? O7 H11 2.515(2) 1_555 4_565 ? C2 C11 3.787(4) 1_555 2_566 ? C3 C3 3.679(6) 1_555 2_666 ? C3 H9 3.123(3) 1_555 3_555 ? C8 C11 3.805(4) 1_555 2_556 ? C9 C11 3.881(4) 1_555 2_556 ? C9 C12 3.782(4) 1_555 2_556 ? C10 C11 3.900(4) 1_555 2_556 ? C10 C12 3.556(4) 1_555 2_556 ? C10 C13 3.774(4) 1_555 2_556 ? C11 C11 3.844(5) 1_555 2_556 ? C11 C12 3.768(4) 1_555 2_556 ? C11 C13 3.734(4) 1_555 2_556 ? C11 H2B 2.865(3) 1_555 2_566 ? #=============================================================================== #==END