# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Shizheng Zhu' 'Qianli Chu' 'Qichen Huang' 'Zheming Want' 'Chunhua Yan' _publ_contact_author_name 'Dr Shizheng Zhu' _publ_contact_author_address ; Shanghai Institute of Organic Chemistry Chinese Academy Sciences 354 Fenglin Lu Shanghai 200032 CHINA ; _publ_contact_author_email ZHUSZ@PUB.SIOC.AC.CN _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Fluorine-containing donor-acceptor complexes: crystallographic study on the interactions between electronegative atoms (N, O, S) and halogen atoms (I, Br)" ; data_Comp3 _database_code_CSD 214914 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 303 _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 Br2 F4 N2' _chemical_formula_weight 374.03 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.2502(3) _cell_length_b 10.4520(4) _cell_length_c 10.5579(3) _cell_angle_alpha 90.00 _cell_angle_beta 127.5085(16) _cell_angle_gamma 90.00 _cell_volume 1334.96(7) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5967 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 29.131 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.861 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 6.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.034 _exptl_absorpt_correction_T_max 0.088 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'NONIUS KappaCCD Diffractometer' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 0.71 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11589 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.88 _diffrn_reflns_theta_max 29.10 _reflns_number_total 1796 _reflns_number_gt 1329 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _publ_section_references ; collect: "Collect" data collection software, Nonius B.V., Delft, The Netherlands, 1998. HKL Scalepack & HKL Denzo: Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R.M. Sweet, Eds., Academic Press, London. absorption correction: R.H. Blessing (1995) Acta Cryst. A51, 33-37. R.H. Blessing (1997) J.Appl. Cryst. 30, 421-426. maXus: S.Mackay, C.J.Gilmore, C.Edwards, M. Tremayne, N. Stuart, K.Shankland maXus: a computer program for the solution and refinement of crystal structures from diffraction data, University of Glasgow, Scotland, UK, Nonius BV, Delft, The Netherlands and MacScience Co. Ltd., Yokohama, Japan (1998). Sheldrick, G. M. (1998). SHELXTL Version 5.1. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1997). SHELX-97. PC Version. University of Goettingen, Germany. ; _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^)+(0.0220P)^2^+4.4380P] 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 0.0111(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1796 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0815 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 Br1 Br 0.09513(3) 0.67436(4) 0.14220(4) 0.05352(17) Uani 1 1 d . . . N1 N 0.2756(2) 0.6658(3) 0.1255(3) 0.0376(6) Uani 1 1 d . . . C1 C 0.3507(3) 0.5825(4) 0.2623(4) 0.0525(9) Uani 1 1 d . . . H1A H 0.4223 0.5835 0.2859 0.079 Uiso 1 1 calc R . . H1B H 0.3223 0.4968 0.2374 0.079 Uiso 1 1 calc R . . H1C H 0.3569 0.6127 0.3533 0.079 Uiso 1 1 calc R . . C2 C 0.3167(3) 0.7967(3) 0.1570(4) 0.0429(8) Uani 1 1 d . . . H2A H 0.3887 0.7978 0.1798 0.051 Uiso 1 1 calc R . . H2B H 0.3253 0.8291 0.2501 0.051 Uiso 1 1 calc R . . C3 C 0.2387(3) 0.8815(3) 0.0162(4) 0.0402(7) Uani 1 1 d . . . H3A H 0.1676 0.8835 -0.0038 0.048 Uiso 1 1 calc R . . H3B H 0.2676 0.9680 0.0395 0.048 Uiso 1 1 calc R . . C4 C -0.0168(8) 0.7148(9) 0.1793(11) 0.048(2) Uani 0.50 1 d P . . C5 C -0.0105(6) 0.6392(9) 0.1786(9) 0.0414(17) Uani 0.50 1 d P . . F1 F -0.11347(18) 0.6765(3) 0.0495(3) 0.0728(8) Uani 1 1 d . . . F2 F -0.0243(8) 0.8381(4) 0.1993(7) 0.076(3) Uani 0.50 1 d P . . F3 F 0.0000 0.5155(3) 0.2500 0.118(2) Uani 1 2 d S . . 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 Br1 0.0501(2) 0.0762(3) 0.0493(2) 0.0000(2) 0.03803(19) -0.0094(2) N1 0.0404(14) 0.0392(15) 0.0417(14) -0.0016(12) 0.0294(12) -0.0025(12) C1 0.056(2) 0.055(2) 0.052(2) 0.0105(18) 0.0354(19) 0.0071(18) C2 0.0467(19) 0.045(2) 0.0405(17) -0.0100(14) 0.0283(16) -0.0091(15) C3 0.0469(18) 0.0343(17) 0.0466(18) -0.0072(14) 0.0322(16) -0.0064(14) C4 0.057(5) 0.049(5) 0.060(5) 0.005(5) 0.047(5) 0.004(5) C5 0.037(4) 0.055(5) 0.038(4) 0.001(4) 0.025(3) 0.003(4) F1 0.0419(11) 0.132(2) 0.0407(11) 0.0192(14) 0.0234(10) 0.0068(14) F2 0.113(8) 0.040(2) 0.137(8) 0.025(3) 0.108(8) 0.023(3) F3 0.118(3) 0.035(2) 0.276(7) 0.000 0.158(4) 0.000 _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 Br1 C5 1.906(7) . ? Br1 C4 2.015(8) . ? N1 C2 1.457(4) . ? N1 C3 1.461(4) 7_565 ? N1 C1 1.463(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.503(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.461(4) 7_565 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 0.796(9) . ? C4 C4 1.248(17) 2 ? C4 F2 1.322(10) . ? C4 F1 1.323(10) . ? C4 C5 1.512(9) 2 ? C4 F2 1.648(10) 2 ? C5 C5 1.337(15) 2 ? C5 F1 1.367(8) . ? C5 F3 1.456(9) . ? C5 C4 1.512(9) 2 ? F2 F2 0.853(13) 2 ? F2 C4 1.648(10) 2 ? F3 C5 1.456(9) 2 ? 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 Br1 C4 23.2(3) . . ? C2 N1 C3 109.0(2) . 7_565 ? C2 N1 C1 111.3(3) . . ? C3 N1 C1 110.4(3) 7_565 . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 110.9(3) . . ? N1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.0 . . ? N1 C3 C2 110.4(3) 7_565 . ? N1 C3 H3A 109.6 7_565 . ? C2 C3 H3A 109.6 . . ? N1 C3 H3B 109.6 7_565 . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C4 92.7(10) . 2 ? C5 C4 F2 172.4(13) . . ? C4 C4 F2 79.7(4) 2 . ? C5 C4 F1 75.8(11) . . ? C4 C4 F1 128.7(9) 2 . ? F2 C4 F1 108.1(8) . . ? C5 C4 C5 61.9(10) . 2 ? C4 C4 C5 31.7(3) 2 2 ? F2 C4 C5 110.4(6) . 2 ? F1 C4 C5 109.2(6) . 2 ? C5 C4 F2 142.4(13) . 2 ? C4 C4 F2 52.1(4) 2 2 ? F2 C4 F2 31.0(5) . 2 ? F1 C4 F2 134.3(7) . 2 ? C5 C4 F2 83.8(5) 2 2 ? C5 C4 Br1 70.7(8) . . ? C4 C4 Br1 116.9(10) 2 . ? F2 C4 Br1 113.6(7) . . ? F1 C4 Br1 106.1(5) . . ? C5 C4 Br1 109.2(5) 2 . ? F2 C4 Br1 110.4(6) 2 . ? C4 C5 C5 86.4(9) . 2 ? C4 C5 F1 69.8(10) . . ? C5 C5 F1 117.7(8) 2 . ? C4 C5 F3 148.4(11) . . ? C5 C5 F3 62.7(3) 2 . ? F1 C5 F3 117.8(6) . . ? C4 C5 C4 55.5(11) . 2 ? C5 C5 C4 31.7(3) 2 2 ? F1 C5 C4 107.2(6) . 2 ? F3 C5 C4 94.2(5) . 2 ? C4 C5 Br1 86.1(9) . . ? C5 C5 Br1 125.2(8) 2 . ? F1 C5 Br1 110.1(5) . . ? F3 C5 Br1 115.8(5) . . ? C4 C5 Br1 110.1(4) 2 . ? C4 F1 C5 34.4(4) . . ? F2 F2 C4 96.1(6) 2 . ? F2 F2 C4 52.9(4) 2 2 ? C4 F2 C4 48.2(7) . 2 ? C5 F3 C5 54.7(6) 2 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.779 _refine_diff_density_min -0.532 _refine_diff_density_rms 0.077 data_Comp4 _database_code_CSD 214915 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 400 _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 F4 I2 N2' _chemical_formula_weight 468.01 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.8483(3) _cell_length_b 10.4899(3) _cell_length_c 10.7354(3) _cell_angle_alpha 90.00 _cell_angle_beta 128.4878(13) _cell_angle_gamma 90.00 _cell_volume 1396.98(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5529 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 30.034 _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 4.526 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.399 _exptl_absorpt_correction_T_max 0.647 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'NONIUS KappaCCD Diffractometer' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 0.71 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13549 _diffrn_reflns_av_R_equivalents 0.0836 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.81 _diffrn_reflns_theta_max 29.96 _reflns_number_total 2011 _reflns_number_gt 1566 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0512P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0109(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2011 _refine_ls_number_parameters 85 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0887 _refine_ls_wR_factor_gt 0.0820 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 I1 I 0.112277(17) 0.67785(2) 0.15128(3) 0.03644(14) Uani 1 1 d . . . N1 N 0.2817(2) 0.6700(2) 0.1324(4) 0.0263(6) Uani 1 1 d . . . C1 C 0.3587(3) 0.5866(4) 0.2663(4) 0.0385(8) Uani 1 1 d . . . H1A H 0.4240 0.5820 0.2785 0.058 Uiso 1 1 calc R . . H1B H 0.3283 0.5029 0.2464 0.058 Uiso 1 1 calc R . . H1C H 0.3743 0.6202 0.3618 0.058 Uiso 1 1 calc R . . C2 C 0.3261(3) 0.7983(3) 0.1559(4) 0.0312(7) Uani 1 1 d . . . H2A H 0.3924 0.7930 0.1690 0.037 Uiso 1 1 calc R . . H2B H 0.3432 0.8349 0.2522 0.037 Uiso 1 1 calc R . . C3 C 0.2474(3) 0.8831(3) 0.0169(4) 0.0308(7) Uani 1 1 d . . . H3A H 0.1828 0.8926 0.0078 0.037 Uiso 1 1 calc R . . H3B H 0.2790 0.9669 0.0348 0.037 Uiso 1 1 calc R . . C5 C -0.0065(6) 0.6399(8) 0.1818(8) 0.0281(14) Uani 0.50 1 d P . . F1 F -0.1077(2) 0.6776(2) 0.0471(3) 0.0557(8) Uani 1 1 d . . . C4 C -0.0128(7) 0.7180(9) 0.1825(10) 0.0363(17) Uani 0.50 1 d P . . F3 F 0.0000 0.5173(3) 0.2500 0.0821(15) Uani 1 2 d S . . F2 F 0.0000 0.8430(4) 0.2500 0.126(3) Uani 1 2 d S . . 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 I1 0.03221(18) 0.0552(2) 0.03290(19) 0.00034(10) 0.02569(15) -0.00659(9) N1 0.0268(14) 0.0297(15) 0.0293(16) -0.0009(11) 0.0209(13) -0.0025(10) C1 0.039(2) 0.046(2) 0.0341(19) 0.0071(17) 0.0246(17) 0.0068(17) C2 0.0324(18) 0.0355(18) 0.0322(19) -0.0084(15) 0.0233(17) -0.0072(14) C3 0.0379(18) 0.0273(18) 0.0385(19) -0.0089(15) 0.0293(17) -0.0084(14) C5 0.022(3) 0.037(4) 0.025(3) 0.001(3) 0.015(3) -0.001(3) F1 0.0271(12) 0.108(2) 0.0295(13) 0.0170(12) 0.0164(11) 0.0051(11) C4 0.036(4) 0.036(4) 0.047(5) 0.004(4) 0.031(4) 0.005(4) F3 0.068(2) 0.0264(17) 0.187(5) 0.000 0.097(3) 0.000 F2 0.177(6) 0.031(2) 0.314(10) 0.000 0.224(7) 0.000 _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 I1 C5 2.139(7) . ? I1 C4 2.246(8) . ? N1 C1 1.461(5) . ? N1 C2 1.466(4) . ? N1 C3 1.474(4) 7_565 ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.503(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.474(4) 7_565 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 C4 0.826(10) . ? C5 C5 1.346(14) 2 ? C5 F1 1.391(8) . ? C5 F3 1.452(8) . ? C5 C4 1.527(10) 2 ? F1 C4 1.354(9) . ? C4 C4 1.238(17) 2 ? C4 F2 1.450(9) . ? C4 C5 1.527(10) 2 ? F3 C5 1.452(8) 2 ? F2 C4 1.450(9) 2 ? 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 I1 C4 21.5(3) . . ? C1 N1 C2 111.3(3) . . ? C1 N1 C3 110.4(3) . 7_565 ? C2 N1 C3 109.1(3) . 7_565 ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 111.1(3) . . ? N1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? N1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? N1 C3 C2 111.1(3) 7_565 . ? N1 C3 H3A 109.4 7_565 . ? C2 C3 H3A 109.4 . . ? N1 C3 H3B 109.4 7_565 . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C4 C5 C5 85.8(7) . 2 ? C4 C5 F1 70.1(8) . . ? C5 C5 F1 115.3(7) 2 . ? C4 C5 F3 147.7(9) . . ? C5 C5 F3 62.4(3) 2 . ? F1 C5 F3 116.7(5) . . ? C4 C5 C4 54.0(9) . 2 ? C5 C5 C4 32.6(4) 2 2 ? F1 C5 C4 104.8(6) . 2 ? F3 C5 C4 94.9(5) . 2 ? C4 C5 I1 86.6(7) . . ? C5 C5 I1 127.9(7) 2 . ? F1 C5 I1 110.1(4) . . ? F3 C5 I1 116.7(4) . . ? C4 C5 I1 111.9(5) 2 . ? C4 F1 C5 35.0(4) . . ? C5 C4 C4 93.3(8) . 2 ? C5 C4 F1 74.9(8) . . ? C4 C4 F1 126.3(9) 2 . ? C5 C4 F2 157.1(10) . . ? C4 C4 F2 64.7(3) 2 . ? F1 C4 F2 122.4(6) . . ? C5 C4 C5 61.5(8) . 2 ? C4 C4 C5 32.7(4) 2 2 ? F1 C4 C5 106.6(6) . 2 ? F2 C4 C5 97.2(6) . 2 ? C5 C4 I1 71.9(7) . . ? C4 C4 I1 119.8(8) 2 . ? F1 C4 I1 106.0(5) . . ? F2 C4 I1 112.5(4) . . ? C5 C4 I1 111.7(5) 2 . ? C5 F3 C5 55.2(6) 2 . ? C4 F2 C4 50.6(7) . 2 ? 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 C1 N1 C2 C3 179.2(3) . . . . ? C3 N1 C2 C3 57.2(4) 7_565 . . . ? N1 C2 C3 N1 -58.4(4) . . . 7_565 ? C4 I1 C5 C5 -82.0(7) . . . 2 ? C4 I1 C5 F1 67.3(8) . . . . ? C4 I1 C5 F3 -156.6(11) . . . . ? C4 I1 C5 C4 -48.8(10) . . . 2 ? C5 C5 F1 C4 75.1(7) 2 . . . ? F3 C5 F1 C4 145.5(10) . . . . ? C4 C5 F1 C4 42.1(8) 2 . . . ? I1 C5 F1 C4 -78.4(8) . . . . ? C5 C5 C4 C4 8.0(9) 2 . . 2 ? F1 C5 C4 C4 126.8(9) . . . 2 ? F3 C5 C4 C4 18(2) . . . 2 ? I1 C5 C4 C4 -120.4(8) . . . 2 ? C5 C5 C4 F1 -118.8(7) 2 . . . ? F3 C5 C4 F1 -108.8(16) . . . . ? C4 C5 C4 F1 -126.8(9) 2 . . . ? I1 C5 C4 F1 112.8(3) . . . . ? C5 C5 C4 F2 23(3) 2 . . . ? F1 C5 C4 F2 142(2) . . . . ? F3 C5 C4 F2 33(4) . . . . ? C4 C5 C4 F2 15.4(18) 2 . . . ? I1 C5 C4 F2 -105(2) . . . . ? F1 C5 C4 C5 118.8(7) . . . 2 ? F3 C5 C4 C5 10.0(12) . . . 2 ? C4 C5 C4 C5 -8.0(9) 2 . . 2 ? I1 C5 C4 C5 -128.4(7) . . . 2 ? C5 C5 C4 I1 128.4(7) 2 . . . ? F1 C5 C4 I1 -112.8(3) . . . . ? F3 C5 C4 I1 138.4(17) . . . . ? C4 C5 C4 I1 120.4(8) 2 . . . ? C5 F1 C4 C4 -82.8(8) . . . 2 ? C5 F1 C4 F2 -163.6(12) . . . . ? C5 F1 C4 C5 -53.5(8) . . . 2 ? C5 F1 C4 I1 65.7(7) . . . . ? C5 I1 C4 C4 83.2(7) . . . 2 ? C5 I1 C4 F1 -67.8(8) . . . . ? C5 I1 C4 F2 156.0(11) . . . . ? C5 I1 C4 C5 47.9(8) . . . 2 ? C4 C5 F3 C5 -11.3(14) . . . 2 ? F1 C5 F3 C5 -106.0(8) . . . 2 ? C4 C5 F3 C5 3.3(4) 2 . . 2 ? I1 C5 F3 C5 120.8(8) . . . 2 ? C5 C4 F2 C4 -17.0(19) . . . 2 ? F1 C4 F2 C4 118.4(10) . . . 2 ? C5 C4 F2 C4 3.6(4) 2 . . 2 ? I1 C4 F2 C4 -113.6(9) . . . 2 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 29.96 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.048 _refine_diff_density_min -1.021 _refine_diff_density_rms 0.161 data_Comp6 _database_code_CSD 214916 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 316 _chemical_formula_moiety ? _chemical_formula_sum 'C7 H11 F4 I2 N O' _chemical_formula_weight 454.97 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' I I -0.4742 1.8119 '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 6.8922(2) _cell_length_b 6.8945(3) _cell_length_c 14.5254(7) _cell_angle_alpha 77.793(3) _cell_angle_beta 81.707(3) _cell_angle_gamma 77.341(3) _cell_volume 654.74(5) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3961 _cell_measurement_theta_min 3.535 _cell_measurement_theta_max 27.480 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 4.828 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'NONIUS KappaCCD Diffractometer' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11693 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 30.06 _reflns_number_total 3690 _reflns_number_gt 3190 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0347P)^2^+1.7737P] 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 0.0113(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3690 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.25664(3) 0.24964(4) 0.101780(16) 0.03201(10) Uani 1 d . . . I2 I 0.83892(4) 0.30385(4) 0.411344(18) 0.03779(11) Uani 1 d . . . O O 0.6766(4) 0.0330(5) 0.3335(2) 0.0407(6) Uani 1 d . . . N N 0.4524(4) -0.1001(5) 0.2165(2) 0.0291(6) Uani 1 d . . . F1 F 0.0876(6) 0.6780(4) 0.0421(3) 0.0745(11) Uani 1 d . . . F2 F 0.2125(4) 0.5334(5) -0.0767(2) 0.0690(10) Uani 1 d . . . F3 F 0.7652(4) 0.6576(5) 0.5002(2) 0.0544(7) Uani 1 d . . . F4 F 1.0149(4) 0.6571(4) 0.38936(18) 0.0502(7) Uani 1 d . . . C1 C 0.1035(6) 0.5091(6) 0.0078(3) 0.0353(8) Uani 1 d . . . C2 C 0.9289(7) 0.5397(7) 0.4624(3) 0.0416(9) Uani 1 d . . . C3 C 0.6700(6) -0.1182(7) 0.1985(3) 0.0362(8) Uani 1 d . . . C4 C 0.7356(6) 0.0449(7) 0.2344(3) 0.0405(9) Uani 1 d . . . C5 C 0.3910(6) -0.1040(6) 0.3176(3) 0.0329(7) Uani 1 d . . . C6 C 0.4648(6) 0.0573(6) 0.3516(3) 0.0361(8) Uani 1 d . . . C7 C 0.3871(7) -0.2602(7) 0.1856(3) 0.0425(9) Uani 1 d . . . H3A H 0.711(10) -0.115(10) 0.137(5) 0.071(19) Uiso 1 d . . . H3B H 0.745(7) -0.259(7) 0.223(3) 0.034(11) Uiso 1 d . . . H4A H 0.887(9) 0.016(9) 0.233(4) 0.058(16) Uiso 1 d . . . H4B H 0.672(7) 0.193(7) 0.198(3) 0.034(11) Uiso 1 d . . . H5A H 0.457(8) -0.227(8) 0.352(4) 0.046(14) Uiso 1 d . . . H5B H 0.244(8) -0.070(8) 0.327(4) 0.046(13) Uiso 1 d . . . H6A H 0.406(7) 0.196(8) 0.321(3) 0.037(12) Uiso 1 d . . . H6B H 0.426(7) 0.051(7) 0.423(4) 0.041(12) Uiso 1 d . . . H7A H 0.421(11) -0.253(11) 0.108(5) 0.08(2) Uiso 1 d . . . H7B H 0.241(8) -0.245(8) 0.201(4) 0.046(13) Uiso 1 d . . . H7C H 0.444(8) -0.384(8) 0.225(4) 0.043(13) 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 I1 0.02886(15) 0.03692(15) 0.02989(14) -0.00057(9) -0.00976(9) -0.00672(9) I2 0.04316(17) 0.03943(16) 0.03698(16) -0.00530(10) -0.01146(11) -0.01823(11) O 0.0424(15) 0.0455(16) 0.0407(15) -0.0042(12) -0.0170(12) -0.0179(12) N 0.0270(14) 0.0357(16) 0.0275(14) -0.0070(12) -0.0058(11) -0.0097(12) F1 0.093(2) 0.0376(15) 0.108(3) -0.0122(16) -0.073(2) -0.0064(15) F2 0.0322(13) 0.084(2) 0.0604(18) 0.0347(16) 0.0055(12) 0.0009(13) F3 0.0339(12) 0.0554(17) 0.078(2) -0.0269(15) -0.0131(13) 0.0006(11) F4 0.0649(17) 0.0554(16) 0.0363(13) 0.0080(11) -0.0121(12) -0.0355(14) C1 0.0307(18) 0.0358(19) 0.0392(19) 0.0022(15) -0.0113(15) -0.0098(15) C2 0.048(2) 0.040(2) 0.041(2) -0.0052(17) -0.0086(18) -0.0164(18) C3 0.0302(18) 0.043(2) 0.0340(19) -0.0065(16) -0.0020(15) -0.0069(16) C4 0.0307(19) 0.051(2) 0.042(2) -0.0009(18) -0.0067(16) -0.0183(17) C5 0.0362(19) 0.0342(19) 0.0306(17) -0.0036(14) -0.0022(15) -0.0148(15) C6 0.041(2) 0.038(2) 0.0321(18) -0.0079(15) -0.0079(16) -0.0110(16) C7 0.049(2) 0.043(2) 0.043(2) -0.0114(18) -0.0129(19) -0.0168(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 I1 C1 2.175(4) . ? I2 C2 2.159(4) . ? O C6 1.424(5) . ? O C4 1.428(5) . ? N C7 1.451(5) . ? N C5 1.466(5) . ? N C3 1.467(5) . ? F1 C1 1.338(5) . ? F2 C1 1.343(5) . ? F3 C2 1.358(5) . ? F4 C2 1.341(5) . ? C1 C1 1.512(7) 2_565 ? C2 C2 1.509(9) 2_766 ? C3 C4 1.509(6) . ? C3 H3A 0.89(7) . ? C3 H3B 1.01(5) . ? C4 H4A 1.02(6) . ? C4 H4B 1.08(5) . ? C5 C6 1.513(5) . ? C5 H5A 0.94(5) . ? C5 H5B 0.98(5) . ? C6 H6A 0.99(5) . ? C6 H6B 1.02(5) . ? C7 H7A 1.11(7) . ? C7 H7B 0.98(5) . ? C7 H7C 0.96(5) . ? 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 O C4 110.0(3) . . ? C7 N C5 110.4(3) . . ? C7 N C3 111.4(3) . . ? C5 N C3 109.4(3) . . ? F1 C1 F2 106.9(4) . . ? F1 C1 C1 108.2(4) . 2_565 ? F2 C1 C1 108.2(4) . 2_565 ? F1 C1 I1 110.2(3) . . ? F2 C1 I1 109.3(3) . . ? C1 C1 I1 113.8(3) 2_565 . ? F4 C2 F3 107.8(4) . . ? F4 C2 C2 109.2(4) . 2_766 ? F3 C2 C2 107.5(5) . 2_766 ? F4 C2 I2 109.2(3) . . ? F3 C2 I2 109.6(3) . . ? C2 C2 I2 113.4(4) 2_766 . ? N C3 C4 110.6(3) . . ? N C3 H3A 111(4) . . ? C4 C3 H3A 111(4) . . ? N C3 H3B 113(3) . . ? C4 C3 H3B 113(3) . . ? H3A C3 H3B 97(5) . . ? O C4 C3 110.7(3) . . ? O C4 H4A 101(3) . . ? C3 C4 H4A 110(3) . . ? O C4 H4B 109(2) . . ? C3 C4 H4B 111(2) . . ? H4A C4 H4B 115(4) . . ? N C5 C6 111.0(3) . . ? N C5 H5A 109(3) . . ? C6 C5 H5A 104(3) . . ? N C5 H5B 108(3) . . ? C6 C5 H5B 106(3) . . ? H5A C5 H5B 119(4) . . ? O C6 C5 110.9(3) . . ? O C6 H6A 108(3) . . ? C5 C6 H6A 113(3) . . ? O C6 H6B 109(3) . . ? C5 C6 H6B 111(3) . . ? H6A C6 H6B 106(4) . . ? N C7 H7A 112(4) . . ? N C7 H7B 109(3) . . ? H7A C7 H7B 108(5) . . ? N C7 H7C 106(3) . . ? H7A C7 H7C 116(5) . . ? H7B C7 H7C 106(4) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 1.471 _refine_diff_density_min -1.208 _refine_diff_density_rms 0.134 data_Comp10 _database_code_CSD 214917 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 363 _chemical_formula_moiety ? _chemical_formula_sum 'C8 H18 F4 I2 N3 O P' _chemical_formula_weight 533.02 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.0280(14) _cell_length_b 16.461(3) _cell_length_c 14.947(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.89(3) _cell_angle_gamma 90.00 _cell_volume 1692.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.092 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 3.846 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26197 _diffrn_reflns_av_R_equivalents 0.0541 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 30.02 _reflns_number_total 4806 _reflns_number_gt 4095 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1111P)^2^+20.6789P] 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 0.0011(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4806 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1886 _refine_ls_wR_factor_gt 0.1818 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.000 _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 I1 I 0.26639(7) 0.61557(3) 0.94292(3) 0.02304(18) Uani 1 1 d . . . I2 I 0.64548(7) 0.36488(3) 0.56299(3) 0.02551(18) Uani 1 1 d . . . P3 P 0.0438(2) 0.27607(11) 0.74432(13) 0.0185(3) Uani 1 1 d . . . O1 O -0.0989(7) 0.2488(3) 0.6619(4) 0.0231(10) Uani 1 1 d . . . F1 F 0.4523(9) 0.5286(4) 1.1056(3) 0.0435(14) Uani 1 1 d . . . F2 F 0.2851(8) 0.4486(3) 1.0049(5) 0.0435(14) Uani 1 1 d . . . F3 F 0.4525(12) 0.4463(4) 0.3979(4) 0.0548(19) Uani 1 1 d . . . N2 N 0.0619(11) 0.3735(4) 0.7667(5) 0.0299(15) Uani 1 1 d . . . F4 F 0.2812(8) 0.4511(4) 0.5020(5) 0.0534(17) Uani 1 1 d . . . N3 N 0.2651(9) 0.2509(4) 0.7330(5) 0.0282(14) Uani 1 1 d . . . N1 N -0.0184(10) 0.2381(4) 0.8372(5) 0.0253(13) Uani 1 1 d . . . C8 C 0.4072(11) 0.5124(4) 1.0154(5) 0.0222(13) Uani 1 1 d . . . C2 C -0.0978(14) 0.1543(6) 0.8283(6) 0.0341(18) Uani 1 1 d . . . C7 C 0.4643(12) 0.4573(5) 0.4873(6) 0.0288(16) Uani 1 1 d . . . C6 C 0.2946(14) 0.1844(6) 0.6728(7) 0.039(2) Uani 1 1 d . . . C3 C -0.0836(13) 0.4165(5) 0.8082(6) 0.0328(18) Uani 1 1 d . . . C5 C 0.4398(13) 0.2733(7) 0.8002(7) 0.040(2) Uani 1 1 d . . . C4 C 0.1603(14) 0.4279(5) 0.7118(7) 0.0362(19) Uani 1 1 d . . . C1 C 0.1008(14) 0.2540(6) 0.9286(6) 0.0351(18) 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 O 0.023(2) 0.019(2) 0.023(2) -0.0013(18) -0.0036(18) 0.0013(18) P 0.0170(7) 0.0156(7) 0.0216(8) -0.0020(6) 0.0014(6) 0.0008(6) N1 0.029(3) 0.017(3) 0.038(4) -0.005(2) -0.003(3) 0.002(2) C1 0.039(4) 0.022(3) 0.034(4) -0.009(3) 0.000(3) 0.011(3) C2 0.036(4) 0.022(4) 0.049(5) 0.003(3) 0.004(4) -0.006(3) N2 0.032(3) 0.022(3) 0.022(3) 0.001(2) 0.005(2) 0.001(2) C3 0.039(4) 0.032(4) 0.030(4) 0.005(3) 0.006(3) -0.009(3) C4 0.042(4) 0.038(4) 0.022(4) -0.002(3) 0.003(3) 0.003(4) N3 0.017(3) 0.030(3) 0.036(4) -0.003(3) 0.002(2) 0.003(2) C5 0.035(4) 0.039(5) 0.043(5) -0.010(4) 0.013(4) 0.009(4) C6 0.023(4) 0.045(5) 0.047(5) -0.002(4) 0.000(3) 0.000(3) I1 0.0230(2) 0.0192(2) 0.0260(3) -0.00384(15) 0.00352(17) -0.00390(15) C7 0.025(3) 0.019(3) 0.023(3) -0.005(2) 0.006(3) 0.000(2) F1 0.059(3) 0.050(3) 0.021(2) -0.004(2) 0.008(2) -0.027(3) F2 0.026(2) 0.028(3) 0.074(4) -0.021(3) 0.006(2) 0.005(2) I2 0.0285(3) 0.0208(3) 0.0247(3) 0.00223(16) 0.00020(18) 0.00418(16) C8 0.031(4) 0.022(3) 0.028(4) -0.001(3) -0.006(3) 0.004(3) F3 0.091(5) 0.038(3) 0.024(3) -0.006(2) -0.014(3) 0.024(3) F4 0.027(3) 0.039(3) 0.089(5) 0.024(3) 0.001(3) 0.002(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 O P 1.489(5) . ? P N1 1.639(6) . ? P N3 1.650(6) . ? P N2 1.664(7) . ? N1 C1 1.469(11) . ? N1 C2 1.473(11) . ? N2 C4 1.466(11) . ? N2 C3 1.481(11) . ? N3 C5 1.453(11) . ? N3 C6 1.458(11) . ? I1 C7 2.143(7) . ? C7 F2 1.344(8) . ? C7 F1 1.349(9) . ? C7 C7 1.526(14) 3_456 ? I2 C8 2.150(7) . ? C8 F3 1.336(10) . ? C8 F4 1.350(10) . ? C8 C8 1.519(15) 3_466 ? 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 O P N1 118.4(3) . . ? O P N3 109.1(3) . . ? N1 P N3 103.5(4) . . ? O P N2 109.1(3) . . ? N1 P N2 102.6(4) . . ? N3 P N2 114.1(4) . . ? C1 N1 C2 112.9(7) . . ? C1 N1 P 121.6(6) . . ? C2 N1 P 120.0(6) . . ? C4 N2 C3 112.4(7) . . ? C4 N2 P 120.9(6) . . ? C3 N2 P 115.6(5) . . ? C5 N3 C6 113.5(7) . . ? C5 N3 P 120.6(6) . . ? C6 N3 P 123.0(6) . . ? F2 C7 F1 106.6(6) . . ? F2 C7 C7 108.8(8) . 3_456 ? F1 C7 C7 108.1(8) . 3_456 ? F2 C7 I1 110.1(5) . . ? F1 C7 I1 109.7(5) . . ? C7 C7 I1 113.2(6) 3_456 . ? F3 C8 F4 106.6(7) . . ? F3 C8 C8 108.9(9) . 3_466 ? F4 C8 C8 108.1(8) . 3_466 ? F3 C8 I2 109.8(5) . . ? F4 C8 I2 110.0(5) . . ? C8 C8 I2 113.2(7) 3_466 . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 7.122 _refine_diff_density_min -1.754 _refine_diff_density_rms 0.360 data_Comp14 _database_code_CSD 214918 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 310 _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 F4 I2 N2 S2' _chemical_formula_weight 652.23 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 6.9160(5) _cell_length_b 7.7021(5) _cell_length_c 10.6364(7) _cell_angle_alpha 80.528(4) _cell_angle_beta 78.781(4) _cell_angle_gamma 85.991(4) _cell_volume 547.75(6) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3048 _cell_measurement_theta_min 3.535 _cell_measurement_theta_max 27.480 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.977 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 310 _exptl_absorpt_coefficient_mu 3.101 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'NONIUS KappaCCD Diffractometer' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10511 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 30.05 _reflns_number_total 3048 _reflns_number_gt 2673 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+0.0086P] 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 0.0181(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3048 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0444 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I I 0.17611(3) 0.16453(2) 0.784291(16) 0.02544(10) Uani 1 d . . . S S 0.25782(12) 0.71642(10) 0.40305(7) 0.02599(18) Uani 1 d . . . F1 F 0.0982(4) -0.1854(2) 0.93069(18) 0.0393(5) Uani 1 d . . . F2 F 0.2395(3) -0.0252(3) 1.03409(19) 0.0393(5) Uani 1 d . . . N N 0.2498(4) 0.4152(3) 0.5513(2) 0.0218(5) Uani 1 d . . . C1 C 0.0991(5) -0.0216(4) 0.9597(3) 0.0241(6) Uani 1 d . . . C2 C 0.2937(4) 0.5301(4) 0.3289(3) 0.0219(6) Uani 1 d . . . C3 C 0.3261(5) 0.5153(5) 0.1968(3) 0.0283(7) Uani 1 d . . . C4 C 0.3482(5) 0.3487(5) 0.1628(3) 0.0301(7) Uani 1 d . . . C5 C 0.3404(5) 0.1988(5) 0.2573(3) 0.0293(7) Uani 1 d . . . C6 C 0.3084(5) 0.2129(4) 0.3874(3) 0.0268(7) Uani 1 d . . . C7 C 0.2850(4) 0.3799(4) 0.4240(3) 0.0212(6) Uani 1 d . . . C8 C 0.2323(4) 0.5832(4) 0.5540(3) 0.0220(6) Uani 1 d . . . C9 C 0.1912(6) 0.6638(5) 0.6750(3) 0.0285(7) Uani 1 d . . . H3 H -0.337(6) 0.391(5) 0.867(4) 0.032(10) Uiso 1 d . . . H4 H -0.349(5) 0.665(5) 0.917(4) 0.020(8) Uiso 1 d . . . H5 H -0.352(6) 0.912(6) 0.763(4) 0.037(11) Uiso 1 d . . . H6 H -0.295(6) 0.894(5) 0.538(4) 0.035(10) Uiso 1 d . . . H91 H -0.062(7) 0.357(6) 0.271(5) 0.062(14) Uiso 1 d . . . H92 H -0.264(10) 0.384(8) 0.272(6) 0.09(2) Uiso 1 d . . . H93 H -0.198(7) 0.211(7) 0.342(5) 0.069(15) 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 I 0.03373(16) 0.02355(14) 0.01652(12) 0.00106(8) -0.00199(8) -0.00118(9) S 0.0328(5) 0.0183(4) 0.0253(4) 0.0001(3) -0.0041(3) -0.0018(3) F1 0.0673(15) 0.0200(9) 0.0242(10) -0.0020(8) 0.0048(10) 0.0014(10) F2 0.0378(12) 0.0521(13) 0.0263(10) 0.0093(9) -0.0138(9) -0.0042(10) N 0.0259(13) 0.0210(12) 0.0173(11) -0.0003(10) -0.0023(10) -0.0022(10) C1 0.0353(18) 0.0206(14) 0.0167(13) -0.0007(11) -0.0074(12) -0.0012(13) C2 0.0220(15) 0.0210(14) 0.0193(13) 0.0013(11) 0.0007(11) 0.0002(11) C3 0.0305(18) 0.0306(17) 0.0197(14) 0.0030(13) -0.0004(12) -0.0019(14) C4 0.0302(18) 0.041(2) 0.0181(15) -0.0067(13) -0.0011(12) -0.0008(15) C5 0.0319(18) 0.0282(17) 0.0299(16) -0.0110(14) -0.0051(14) -0.0015(14) C6 0.0310(18) 0.0238(15) 0.0244(15) -0.0027(13) -0.0034(13) 0.0000(13) C7 0.0217(15) 0.0213(14) 0.0189(13) -0.0001(11) -0.0024(11) -0.0003(12) C8 0.0209(15) 0.0233(14) 0.0201(14) -0.0001(12) -0.0020(11) -0.0029(12) C9 0.0283(18) 0.0304(18) 0.0276(16) -0.0098(14) -0.0016(14) -0.0027(14) _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 I C1 2.159(3) . ? S C2 1.730(3) . ? S C8 1.742(3) . ? F1 C1 1.348(4) . ? F2 C1 1.363(4) . ? N C8 1.296(4) . ? N C7 1.397(4) . ? C1 C1 1.515(6) 2_557 ? C2 C3 1.401(4) . ? C2 C7 1.402(4) . ? C3 C4 1.380(5) . ? C4 C5 1.397(5) . ? C5 C6 1.380(5) . ? C6 C7 1.394(4) . ? C8 C9 1.490(4) . ? 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 C2 S C8 89.61(14) . . ? C8 N C7 111.1(2) . . ? F1 C1 F2 106.6(3) . . ? F1 C1 C1 109.1(3) . 2_557 ? F2 C1 C1 108.3(3) . 2_557 ? F1 C1 I 110.06(18) . . ? F2 C1 I 109.4(2) . . ? C1 C1 I 113.2(3) 2_557 . ? C3 C2 C7 121.0(3) . . ? C3 C2 S 129.7(2) . . ? C7 C2 S 109.3(2) . . ? C4 C3 C2 118.2(3) . . ? C3 C4 C5 121.0(3) . . ? C6 C5 C4 121.0(3) . . ? C5 C6 C7 119.0(3) . . ? C6 C7 N 125.6(3) . . ? C6 C7 C2 119.9(3) . . ? N C7 C2 114.5(3) . . ? N C8 C9 124.3(3) . . ? N C8 S 115.5(2) . . ? C9 C8 S 120.2(2) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 30.05 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 1.415 _refine_diff_density_min -1.835 _refine_diff_density_rms 0.151 data_Comp17 _database_code_CSD 214919 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 318 _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 F4 I2 N2' _chemical_formula_weight 433.91 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 6.2536(5) _cell_length_b 6.4403(7) _cell_length_c 7.5067(7) _cell_angle_alpha 106.843(5) _cell_angle_beta 107.535(6) _cell_angle_gamma 93.925(6) _cell_volume 271.87(4) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4840 _cell_measurement_theta_min 3.47 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.650 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 5.803 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.295 _exptl_absorpt_correction_T_max 0.376 _exptl_absorpt_process_details '(Blessing, 1995, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'NONIUS KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 0.76 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4840 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 27.45 _reflns_number_total 1214 _reflns_number_gt 1172 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _publ_section_references ; collect: "Collect" data collection software, Nonius B.V., Delft, The Netherlands, 1998. HKL Scalepack & HKL Denzo: Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R.M. Sweet, Eds., Academic Press. absorption correction: R.H. Blessing (1995) Acta Cryst. A51, 33-37. R.H. Blessing (1997) J.Appl. Cryst. 30, 421-426. maXus: S.Mackay, C.J.Gilmore, C.Edwards, M. Tremayne, N. Stuart, K.Shankland maXus: a computer program for the solution and refinement of crystal structures from diffraction data, University of Glasgow, Scotland, UK, Nonius BV, Delft, The Netherlands and MacScience Co. Ltd., Yokohama, Japan (1998). Sheldrick, G. M. (1998). SHELXTL Version 5.1. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1997). SHELX-97. PC Version. University of Goettingen, Germany. ; _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^)+(0.0432P)^2^+0.7154P] 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(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1214 _refine_ls_number_parameters 65 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0856 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _refine_ls_shift/su_max 0.000 _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 I1 I -0.19439(5) -0.20659(5) 0.16898(5) 0.0348(2) Uani 1 1 d . . . C1 C 0.0107(9) -0.1133(9) 0.0112(8) 0.0337(11) Uani 1 1 d . . . F1 F 0.2332(6) -0.1089(7) 0.1067(6) 0.0527(10) Uani 1 1 d . . . F2 F -0.0461(7) -0.2621(6) -0.1699(5) 0.0491(9) Uani 1 1 d . . . N1 N -0.4265(9) -0.3869(9) 0.3908(8) 0.0420(11) Uani 1 1 d . . . C2 C -0.5691(10) -0.3162(10) 0.4868(9) 0.0402(12) Uani 1 1 d . . . H2 H -0.6226 -0.1865 0.4798 0.048 Uiso 1 1 calc R . . C3 C -0.3595(11) -0.5733(11) 0.4044(9) 0.0425(13) Uani 1 1 d . . . H3 H -0.2615 -0.6313 0.3387 0.051 Uiso 1 1 calc R . . 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 I1 0.0375(3) 0.0387(3) 0.0367(3) 0.01777(16) 0.01966(17) 0.00464(15) C1 0.031(2) 0.037(3) 0.037(3) 0.014(2) 0.017(2) 0.007(2) F1 0.0326(17) 0.075(3) 0.073(3) 0.048(2) 0.0224(17) 0.0236(17) F2 0.071(2) 0.0355(17) 0.0465(19) 0.0037(14) 0.0384(19) 0.0027(16) N1 0.047(3) 0.046(3) 0.040(3) 0.020(2) 0.021(2) 0.003(2) C2 0.039(3) 0.037(3) 0.049(3) 0.018(2) 0.018(2) 0.005(2) C3 0.040(3) 0.046(3) 0.044(3) 0.011(2) 0.022(2) 0.005(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 I1 C1 2.152(5) . ? C1 F2 1.342(7) . ? C1 F1 1.354(6) . ? C1 C1 1.527(11) 2 ? N1 C3 1.320(9) . ? N1 C2 1.332(8) . ? C2 C3 1.374(8) 2_446 ? C2 H2 0.9300 . ? C3 C2 1.374(8) 2_446 ? C3 H3 0.9300 . ? 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 F2 C1 F1 107.6(5) . . ? F2 C1 C1 108.2(6) . 2 ? F1 C1 C1 107.0(6) . 2 ? F2 C1 I1 109.9(4) . . ? F1 C1 I1 110.0(4) . . ? C1 C1 I1 113.8(5) 2 . ? C3 N1 C2 115.6(5) . . ? N1 C2 C3 122.8(6) . 2_446 ? N1 C2 H2 118.6 . . ? C3 C2 H2 118.6 2_446 . ? N1 C3 C2 121.6(6) . 2_446 ? N1 C3 H3 119.2 . . ? C2 C3 H3 119.2 2_446 . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 2.247 _refine_diff_density_min -0.845 _refine_diff_density_rms 0.160 data_Comp18 _database_code_CSD 214920 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 312 _chemical_formula_moiety ? _chemical_formula_sum 'C7 H6 F4 I2 N2' _chemical_formula_weight 447.94 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.9365(5) _cell_length_b 11.5354(10) _cell_length_c 8.1604(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.487(4) _cell_angle_gamma 90.00 _cell_volume 611.66(8) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7820 _cell_measurement_theta_min 3.53 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 5.163 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.259 _exptl_absorpt_correction_T_max 0.529 _exptl_absorpt_process_details '(Blessing, 1995, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'NONIUS KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 0.76 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7820 _diffrn_reflns_av_R_equivalents 0.0590 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1391 _reflns_number_gt 1124 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _publ_section_references ; collect: "Collect" data collection software, Nonius B.V., Delft, The Netherlands, 1998. HKL Scalepack & HKL Denzo: Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R.M. Sweet, Eds., Academic Press. absorption correction: R.H. Blessing (1995) Acta Cryst. A51, 33-37. R.H. Blessing (1997) J.Appl. Cryst. 30, 421-426. maXus: S.Mackay, C.J.Gilmore, C.Edwards, M. Tremayne, N. Stuart, K.Shankland maXus: a computer program for the solution and refinement of crystal structures from diffraction data, University of Glasgow, Scotland, UK, Nonius BV, Delft, The Netherlands and MacScience Co. Ltd., Yokohama, Japan (1998). Sheldrick, G. M. (1998). SHELXTL Version 5.1. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1997). SHELX-97. PC Version. University of Goettingen, Germany. ; _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^)+(0.0456P)^2^+2.6535P] 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 0.027(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1391 _refine_ls_number_parameters 78 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1167 _refine_ls_wR_factor_gt 0.1080 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _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 I1 I 0.24608(7) 0.16138(5) -0.01208(6) 0.0654(3) Uani 1 1 d . . . F1 F 0.0663(8) -0.0567(4) -0.1713(6) 0.0755(14) Uani 1 1 d . . . F2 F 0.2294(7) -0.0732(4) 0.1091(6) 0.0734(13) Uani 1 1 d . . . N1 N 0.4367(13) 0.3886(9) 0.0086(9) 0.087(3) Uani 1 1 d D . . C1 C 0.1010(11) -0.0034(7) -0.0163(8) 0.0593(19) Uani 1 1 d . . . C2 C 0.329(2) 0.4772(12) 0.0380(11) 0.092(4) Uani 1 1 d D . . H2 H 0.2121 0.4633 0.0655 0.110 Uiso 1 1 calc R . . C3 C 0.6078(15) 0.4119(10) -0.0276(10) 0.078(3) Uani 1 1 d D . . H3 H 0.69(3) 0.351(19) -0.046(10) 0.094 Uiso 0.50 1 d PD . . C4 C 0.714(3) 0.331(2) -0.050(2) 0.063(4) Uani 0.50 1 d P . . H4A H 0.7609 0.2841 0.0533 0.095 Uiso 0.50 1 calc PR . . H4B H 0.8298 0.3620 -0.0737 0.095 Uiso 0.50 1 calc PR . . H4C H 0.6320 0.2848 -0.1474 0.095 Uiso 0.50 1 calc PR . . 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 I1 0.0617(4) 0.0869(5) 0.0454(3) 0.0014(2) 0.0160(2) -0.0357(2) F1 0.088(3) 0.092(3) 0.059(2) -0.022(2) 0.041(2) -0.038(3) F2 0.058(3) 0.075(3) 0.077(3) 0.011(2) 0.011(2) -0.013(2) N1 0.089(6) 0.115(7) 0.045(4) 0.007(4) 0.010(4) -0.073(5) C1 0.052(4) 0.084(5) 0.041(3) -0.001(4) 0.015(3) -0.019(4) C2 0.094(7) 0.128(10) 0.049(4) -0.004(5) 0.021(5) -0.075(7) C3 0.074(6) 0.105(8) 0.044(4) 0.008(4) 0.007(4) -0.044(5) C4 0.051(9) 0.073(11) 0.072(10) 0.012(8) 0.029(7) 0.012(7) _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 I1 C1 2.145(8) . ? F1 C1 1.350(8) . ? F2 C1 1.360(9) . ? N1 C2 1.334(15) . ? N1 C3 1.347(12) . ? C1 C1 1.517(14) 3 ? C2 C3 1.364(14) 3_665 ? C2 H2 0.9300 . ? C3 C4 1.238(17) . ? C3 C2 1.364(14) 3_665 ? C3 H3 0.93(2) . ? C4 H3 0.31(3) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? 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 C2 N1 C3 118.4(9) . . ? F1 C1 F2 106.9(7) . . ? F1 C1 C1 108.4(7) . 3 ? F2 C1 C1 107.5(7) . 3 ? F1 C1 I1 110.3(4) . . ? F2 C1 I1 109.4(4) . . ? C1 C1 I1 114.1(8) 3 . ? N1 C2 C3 119.8(10) . 3_665 ? N1 C2 H2 120.1 . . ? C3 C2 H2 120.1 3_665 . ? C4 C3 N1 119.7(15) . . ? C4 C3 C2 118.5(15) . 3_665 ? N1 C3 C2 121.8(11) . 3_665 ? C4 C3 H3 1(10) . . ? N1 C3 H3 119(10) . . ? C2 C3 H3 119(10) 3_665 . ? C3 C4 H3 3(10) . . ? C3 C4 H4A 109.5 . . ? H3 C4 H4A 111.1 . . ? C3 C4 H4B 109.5 . . ? H3 C4 H4B 110.8 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H3 C4 H4C 106.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.050 _refine_diff_density_min -2.071 _refine_diff_density_rms 0.230