# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2002 data_octafluoro_1,2_dimethylenecyclobutane _publ_contact_author_name # Name of author for correspondence ; Prof. Dr. Peter Luger ; _publ_contact_author_address # address of author for correspondence ; Institut f\"ur Chemie Kristallographie Freie Universit\"at Berlin Takustr. 6 14195 Berlin Germany ; _publ_contact_author_email 'luger@chemie.fu-berlin.de' _publ_contact_author_fax '0049-30-83853464' _publ_contact_author_phone '0049-30-83853411' _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Experimental charge density of octafluoro-1,2-dimethylenecyclobutane: atomic volumes and charges in a perfluorinated hydrocarbon. ; loop_ _publ_author_name _publ_author_address 'Lentz, Dieter' # author name ; Institut f\"ur Chemie Anorgnaische Chemie Freie Universit\"at Berlin Fabeckstr. 34-36 14195 Berlin ; 'Patzsche, Mona' ; ; 'Bach, Ansgar' ; Institut f\"ur Chemie Kristallographie Freie Universit\"at Berlin Takustr. 6 14195 Berlin ; 'Scheins, Stephan' ; ; 'Luger, Peter' ; ; #=============================================================================== # TEXT _publ_section_abstract ; ? ; # Insert blank lines between paragraphs _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; # Insert blank lines between references _publ_section_references ; Allen, F.H. & Kennard, O. (1993). Chem. Des. Autom. News., 8, 31-37. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C. Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R. (1999) J. Appl. Cryst. 32, 115-119. Beurskens, P.T., Admiraal, G., Beurskens, G., Bosman, W.P., Garc\'ia-Granda, S., Gould, R.O., Smits, J.M.M. & Smykalla, C. (1999) The DIRDIF99 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410. Boeyens, J.C.A. (1978). J.Cryst.Mol.Struct. 8, 317-320. Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358. Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft, The Netherlands. Flack, H.D. (1983). Acta Cryst. A39, 876-881. LePage, Y. (1987). J. Appl. Cryst. 20, 264-269. Mackay, A.L. (1984). Acta Cryst. A40, 165-166. Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018. Nonius (1998). Collect Software, Nonius, Delft, The Netherlands. North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968). Acta Cryst. A24, 351-359. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, 276, 307-326. Sheldrick, G.M. SHELXL93. Program for crystal structure refinement. University of G\"ottingen, Germany, 1993. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of G\"ottingen, Germany, 1997. Sheldrick, G.M. SHELXS86. Program for Crystal Structure solution. University of G\"ottingen, Germany, 1986. Sheldrick, G.M. SHELXS97. Program for Crystal Structure solution. University of G\"ottingen, Germany, 1997. Spek, A.L. (1987). Acta Cryst. C43, 1233-1235. Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579. Spek, A.L. (1990). Acta Cryst. A46, C-34. Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht University, The Netherlands. Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66. Wilson, A.J.C. (1992) Ed. International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands. ; #_publ_section_figure_captions #; # ? #; _publ_section_acknowledgements ; ? ; _publ_section_figure_captions ; View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. ; #=============================================================================== data_ac #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; octafluoro-1,2-dimethylenecyclobutane ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 F8' _chemical_formula_structural ? _chemical_formula_sum 'C6 F8' _chemical_formula_weight 224.06 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,1/2+y,1/2-z' '-x,-y,-z' 'x,1/2-y,1/2+z' _cell_length_a 8.134(1) _cell_length_b 7.1110(8) _cell_length_c 12.699(2) _cell_angle_alpha 90 _cell_angle_beta 100.87(1) _cell_angle_gamma 90 _cell_volume 721.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 27039 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 51.9 _cell_special_details ; ? ; _exptl_crystal_description 'cylinder' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_size_rad 0.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.063 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.251 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # cylinder 'cylindrical' # empirical 'empirical from intensities' # gaussian 'Gaussian from crystal shape' # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # refdelf 'refined from delta-F' # sphere 'spherical' _exptl_absorpt_correction_type 'empirical' # Example: '(North, Phillips & Mathews, 1968)' _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 0.88 #=============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; A Bruker AXS low temerature device was used. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD diffractometer' _diffrn_measurement_method '\w and \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number no _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 48515 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 53.49 _diffrn_reflns_theta_full ? _diffrn_measured_fraction_theta_max ? _diffrn_measured_fraction_theta_full ? _reflns_number_total 8383 _reflns_number_gt 5127 _reflns_threshold_expression 'I > 3 \s(I)' _computing_data_collection 'Bruker AXS SMART CCD diffractometer' _computing_cell_refinement 'SMART, SAINT (Siemens, 1996)' _computing_data_reduction 'SMART (Siemens, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'Koritsanszky et al, (1995)' _computing_molecular_graphics 'Koritsanszky et al, (1995)' _computing_publication_material 'PLATON (Spek, 1990)' #=============================================================================== # REFINEMENT DATA _refine_special_details ? _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'sigma' #_refine_ls_weighting_details 'w=1/\s' _atom_sites_solution_primary 'direct' _atom_sites_solution_secondary 'difmap' _atom_sites_solution_hydrogens 'geom' _refine_ls_hydrogen_treatment ' no hydrogen in the molecule' _refine_ls_extinction_method ? _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack none _refine_ls_number_reflns 5127 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all ? _refine_ls_R_factor_gt 0.031 _refine_ls_wR_factor_ref 0.041 _refine_ls_wR_factor_gt ? _refine_ls_goodness_of_fit_ref 2.52 _refine_ls_restrained_S_all ? _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.003 _refine_diff_density_max 0.19 _refine_diff_density_min -0.26 _refine_diff_density_rms ? #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags F1 F Uani 0.86839(8) 0.53597(12) 0.88150(5) 1.000 0.0373(2) . . F2 F Uani 0.93774(9) 0.78456(10) 0.97794(6) 1.000 0.0369(2) . . F3 F Uani 0.92545(9) 1.13467(9) 0.79856(5) 1.000 0.0322(1) . . F4 F Uani 0.69354(8) 1.12534(9) 0.85942(6) 1.000 0.0334(2) . . F5 F Uani 0.52212(10) 1.06798(9) 0.66081(5) 1.000 0.0368(2) . . F6 F Uani 0.75312(9) 1.08903(8) 0.59928(6) 1.000 0.0339(1) . . F7 F Uani 0.59126(8) 0.67890(9) 0.52642(6) 1.000 0.0342(2) . . F8 F Uani 0.70099(10) 0.48228(11) 0.64956(6) 1.000 0.0427(2) . . C1 C Uani 0.86507(10) 0.71946(12) 0.88415(6) 1.000 0.0252(2) . . C2 C Uani 0.79655(9) 0.82834(10) 0.80304(6) 1.000 0.0191(1) . . C3 C Uani 0.78104(10) 1.03937(10) 0.79346(7) 1.000 0.0214(1) . . C4 C Uani 0.68205(10) 1.00930(11) 0.67570(6) 1.000 0.0220(2) . . C5 C Uani 0.70957(9) 0.80101(10) 0.69275(6) 1.000 0.0186(1) . . C6 C Uani 0.66899(10) 0.65858(11) 0.62593(6) 1.000 0.0249(2) . . 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 0.0469(4) 0.0270(3) 0.0357(3) 0.0095(2) 0.0017(2) 0.0047(2) F2 0.0383(3) 0.0481(4) 0.0210(2) -0.0003(2) -0.0028(2) 0.0019(3) F3 0.0300(2) 0.0291(2) 0.0380(3) -0.0056(2) 0.0073(2) -0.0123(2) F4 0.0367(3) 0.0318(2) 0.0345(3) -0.0108(2) 0.0135(2) 0.0059(2) F5 0.0278(3) 0.0387(3) 0.0411(3) -0.0011(2) -0.0006(2) 0.0152(2) F6 0.0490(3) 0.0257(2) 0.0290(2) 0.0069(2) 0.0122(3) -0.0023(2) F7 0.0378(3) 0.0390(3) 0.0231(3) -0.0059(2) -0.0012(2) -0.0079(2) F8 0.0633(4) 0.0188(2) 0.0423(3) -0.0052(2) 0.0002(3) -0.0034(2) C1 0.0263(3) 0.0281(3) 0.0202(2) 0.0031(2) 0.0017(2) 0.0023(2) C2 0.0184(2) 0.0205(2) 0.0182(2) -0.0004(2) 0.0031(2) 0.0001(2) C3 0.0207(2) 0.0200(2) 0.0245(3) -0.0046(2) 0.0069(2) -0.0011(2) C4 0.0222(3) 0.0203(2) 0.0237(3) 0.0016(2) 0.0046(2) 0.0032(2) C5 0.0183(2) 0.0186(2) 0.0187(2) -0.0012(2) 0.0028(2) -0.0012(2) C6 0.0293(3) 0.0210(2) 0.0232(3) -0.0040(2) 0.0018(2) -0.0043(2) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 F1 C1 1.3056(12) . . yes F2 C1 1.3102(11) . . yes F3 C3 1.3470(11) . . yes F4 C3 1.3441(11) . . yes F5 C4 1.3451(11) . . yes F6 C4 1.3450(11) . . yes F7 C6 1.3100(11) . . yes F8 C6 1.3038(11) . . yes C1 C2 1.3246(11) . . no C2 C3 1.5089(10) . . no C2 C5 1.4581(11) . . no C3 C4 1.5736(12) . . no C4 C5 1.5075(11) . . no C5 C6 1.3225(11) . . no 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 F1 C1 F2 111.63(7) . . . yes F1 C1 C2 124.88(7) . . . yes F2 C1 C2 123.50(8) . . . yes C1 C2 C3 131.34(7) . . . no C1 C2 C5 136.53(7) . . . no C3 C2 C5 92.12(6) . . . no F3 C3 F4 107.49(7) . . . yes F3 C3 C2 115.95(7) . . . yes F3 C3 C4 113.54(7) . . . yes F4 C3 C2 116.62(7) . . . yes F4 C3 C4 114.70(7) . . . yes C2 C3 C4 87.79(6) . . . no F5 C4 F6 107.68(7) . . . yes F5 C4 C3 113.54(6) . . . yes F5 C4 C5 116.01(7) . . . yes F6 C4 C3 114.57(7) . . . yes F6 C4 C5 116.45(7) . . . yes C3 C4 C5 87.79(6) . . . no C2 C5 C4 92.24(6) . . . no C2 C5 C6 137.35(7) . . . no C4 C5 C6 130.39(7) . . . no F7 C6 F8 111.54(7) . . . yes F7 C6 C5 123.44(7) . . . yes F8 C6 C5 125.02(7) . . . yes 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 F1 C1 C2 C3 179.40(8) . . . . no F1 C1 C2 C5 -0.43(16) . . . . no F2 C1 C2 C3 -0.24(14) . . . . no F2 C1 C2 C5 179.93(9) . . . . no C1 C2 C3 F3 66.65(12) . . . . no C1 C2 C3 F4 -61.51(12) . . . . no C1 C2 C3 C4 -178.16(9) . . . . no C5 C2 C3 F3 -113.46(8) . . . . no C5 C2 C3 F4 118.37(8) . . . . no C5 C2 C3 C4 1.73(6) . . . . no C1 C2 C5 C4 178.07(10) . . . . no C1 C2 C5 C6 -3.79(17) . . . . no C3 C2 C5 C4 -1.81(6) . . . . no C3 C2 C5 C6 176.33(10) . . . . no F3 C3 C4 F5 -126.73(7) . . . . no F3 C3 C4 F6 -2.43(10) . . . . no F3 C3 C4 C5 115.77(7) . . . . no F4 C3 C4 F5 -2.59(10) . . . . no F4 C3 C4 F6 121.71(8) . . . . no F4 C3 C4 C5 -120.09(7) . . . . no C2 C3 C4 F5 115.83(7) . . . . no C2 C3 C4 F6 -119.87(7) . . . . no C2 C3 C4 C5 -1.67(6) . . . . no F5 C4 C5 C2 -113.48(7) . . . . no F5 C4 C5 C6 68.18(11) . . . . no F6 C4 C5 C2 118.20(7) . . . . no F6 C4 C5 C6 -60.14(12) . . . . no C3 C4 C5 C2 1.73(6) . . . . no C3 C4 C5 C6 -176.61(9) . . . . no C2 C5 C6 F7 -177.96(8) . . . . no C2 C5 C6 F8 1.72(16) . . . . no C4 C5 C6 F7 -0.40(14) . . . . no C4 C5 C6 F8 179.27(8) . . . . no 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 F1 F3 3.1068(10) . 1_545 no F1 F8 3.0269(10) . . no F1 F5 3.1283(11) . 2_646 no F1 F6 3.0653(10) . 2_746 no F1 F2 3.1315(11) . 3_767 no F2 F1 3.1315(11) . 3_767 no F2 F3 2.9038(10) . 3_777 no F2 F7 3.0072(10) . 4_565 no F2 C6 3.1659(11) . 4_565 no F3 F1 3.1068(10) . 1_565 no F3 F6 2.6714(10) . . no F3 C1 3.1845(10) . 2_756 no F3 C2 3.1264(10) . 2_756 no F3 C5 3.1782(10) . 2_756 no F3 C6 3.2615(11) . 2_756 no F3 F2 2.9038(10) . 3_777 no F4 F5 2.6731(10) . . no F4 F7 2.9798(10) . 2_656 no F4 C6 2.9988(11) . 2_656 no F5 F4 2.6731(10) . . no F5 F1 3.1283(11) . 2_656 no F5 C1 3.2752(12) . 2_656 no F5 C2 3.2872(11) . 2_656 no F5 C5 3.3282(10) . 2_656 no F5 F7 2.9860(10) . 3_676 no F6 F3 2.6714(10) . . no F6 F8 2.9171(10) . 1_565 no F6 F1 3.0653(10) . 2_756 no F6 C1 3.2098(11) . 2_756 no F7 F4 2.9798(10) . 2_646 no F7 F5 2.9860(10) . 3_676 no F7 F7 2.9584(9) . 3_666 no F7 F2 3.0072(10) . 4_564 no F7 C1 3.2037(11) . 4_564 no F8 F1 3.0269(10) . . no F8 F6 2.9171(10) . 1_545 no C1 F3 3.1845(10) . 2_746 no C1 F5 3.2752(11) . 2_646 no C1 F6 3.2098(11) . 2_746 no C1 F7 3.2037(11) . 4_565 no C2 F3 3.1264(10) . 2_746 no C2 F5 3.2872(11) . 2_646 no C5 F3 3.1782(10) . 2_746 no C5 F5 3.3282(10) . 2_646 no C6 F3 3.2615(11) . 2_746 no C6 F4 2.9988(11) . 2_646 no C6 F2 3.1659(11) . 4_564 no # End of Crystallographic Information File