Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Jurg Hulliger' _publ_contact_author_address ; Department of Chemistry and Biochemistry University of Berne Freiestrasse 3 Berne CH-3012 SWITZERLAND ; _publ_contact_author_email PUBLICATION.HULLIGER@IAC.UNIBE.CH _publ_section_title ; Synthesis and Crystal Engineering of Fluorinated Stilbenes ; loop_ _publ_author_name 'Raul Mariaca' 'Patrick Eggli' Stoeckli-Evans 'Norwid-Rasmus Behrnd' 'Jurg Hulliger' data_CF4H4B _database_code_depnum_ccdc_archive 'CCDC 291488' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H6 Br F4 N' _chemical_formula_sum 'C15 H6 Br F4 N' _chemical_formula_weight 356.12 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' Br Br -0.2901 2.4595 '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' N N 0.0061 0.0033 '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 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.3134(10) _cell_length_b 11.0006(8) _cell_length_c 12.5519(14) _cell_angle_alpha 90.00 _cell_angle_beta 97.193(13) _cell_angle_gamma 90.00 _cell_volume 1275.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 26.02 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.854 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 3.261 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.167 _exptl_absorpt_correction_T_max 0.235 _exptl_absorpt_process_details 'MULscanABS in PLATON (Spek, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9773 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 26.06 _reflns_number_total 2493 _reflns_number_gt 2083 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON99 (Spek, 2003)' _computing_publication_material SHELXL-97 _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^)+(0.0468P)^2^] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2493 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_ref 0.0702 _refine_ls_wR_factor_gt 0.0673 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 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 -0.21979(3) 0.07693(2) -0.150836(18) 0.02880(10) Uani 1 1 d . . . F1 F 0.45793(17) 0.53446(14) 0.18992(11) 0.0370(4) Uani 1 1 d . . . F2 F 0.65325(17) 0.70095(14) 0.25617(11) 0.0383(4) Uani 1 1 d . . . F3 F 0.54572(16) 0.91375(11) -0.06847(11) 0.0307(3) Uani 1 1 d . . . F4 F 0.34613(17) 0.75050(13) -0.13608(10) 0.0338(3) Uani 1 1 d . . . N1 N 0.8016(2) 0.9684(2) 0.16487(17) 0.0344(5) Uani 1 1 d . . . C1 C -0.0865(2) 0.19833(19) -0.09550(18) 0.0231(5) Uani 1 1 d . . . C2 C -0.0268(3) 0.1911(2) 0.01064(18) 0.0263(5) Uani 1 1 d . . . H2A H -0.0532 0.1274 0.0555 0.032 Uiso 1 1 calc R . . C3 C 0.0725(3) 0.2788(2) 0.05028(18) 0.0269(5) Uani 1 1 d . . . H3A H 0.1136 0.2752 0.1234 0.032 Uiso 1 1 calc R . . C4 C 0.1136(2) 0.3724(2) -0.01467(18) 0.0231(5) Uani 1 1 d . . . C5 C 0.0482(3) 0.3784(2) -0.12094(18) 0.0251(5) Uani 1 1 d . . . H5A H 0.0731 0.4426 -0.1658 0.030 Uiso 1 1 calc R . . C6 C -0.0525(3) 0.2921(2) -0.16196(18) 0.0251(5) Uani 1 1 d . . . H6A H -0.0972 0.2971 -0.2341 0.030 Uiso 1 1 calc R . . C7 C 0.2231(3) 0.4593(2) 0.03259(18) 0.0253(5) Uani 1 1 d . . . H7A H 0.2563 0.4508 0.1069 0.030 Uiso 1 1 calc R . . C8 C 0.2799(3) 0.5491(2) -0.02001(18) 0.0248(5) Uani 1 1 d . . . H8A H 0.2453 0.5573 -0.0941 0.030 Uiso 1 1 calc R . . C9 C 0.3895(2) 0.6359(2) 0.02435(17) 0.0219(5) Uani 1 1 d . . . C10 C 0.4728(3) 0.6289(2) 0.12438(19) 0.0253(5) Uani 1 1 d . . . C11 C 0.5766(3) 0.7136(2) 0.15957(18) 0.0257(5) Uani 1 1 d . . . C12 C 0.6049(2) 0.8121(2) 0.09615(18) 0.0230(5) Uani 1 1 d . . . C13 C 0.5235(3) 0.82086(19) -0.00416(18) 0.0237(5) Uani 1 1 d . . . C14 C 0.4206(2) 0.7359(2) -0.03808(17) 0.0230(5) Uani 1 1 d . . . C15 C 0.7140(3) 0.8997(2) 0.13345(18) 0.0265(5) 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 Br1 0.03070(15) 0.02514(14) 0.03043(15) -0.00250(9) 0.00330(9) -0.00883(10) F1 0.0389(9) 0.0373(8) 0.0319(8) 0.0147(6) -0.0071(6) -0.0151(7) F2 0.0368(8) 0.0453(8) 0.0293(7) 0.0096(6) -0.0096(6) -0.0139(7) F3 0.0394(8) 0.0255(7) 0.0271(7) 0.0051(5) 0.0038(6) -0.0097(6) F4 0.0416(9) 0.0329(7) 0.0241(7) 0.0049(6) -0.0071(6) -0.0098(6) N1 0.0325(12) 0.0341(11) 0.0365(12) -0.0065(9) 0.0039(9) -0.0123(10) C1 0.0206(11) 0.0216(10) 0.0273(11) -0.0024(9) 0.0044(9) -0.0003(9) C2 0.0280(13) 0.0246(11) 0.0267(12) 0.0053(9) 0.0048(9) -0.0028(10) C3 0.0253(12) 0.0308(12) 0.0236(11) 0.0051(9) -0.0008(9) -0.0037(10) C4 0.0181(11) 0.0245(11) 0.0268(11) -0.0009(9) 0.0035(9) -0.0016(9) C5 0.0285(12) 0.0228(11) 0.0248(11) 0.0032(9) 0.0063(9) -0.0032(10) C6 0.0270(12) 0.0250(11) 0.0231(11) 0.0001(9) 0.0025(9) -0.0004(10) C7 0.0240(12) 0.0284(11) 0.0231(11) 0.0004(9) 0.0010(9) -0.0008(10) C8 0.0233(12) 0.0255(11) 0.0255(11) -0.0012(9) 0.0025(9) -0.0020(9) C9 0.0203(11) 0.0228(11) 0.0230(11) -0.0013(8) 0.0046(9) -0.0005(9) C10 0.0262(12) 0.0236(11) 0.0272(12) 0.0038(9) 0.0068(9) -0.0027(10) C11 0.0208(11) 0.0329(12) 0.0226(11) 0.0009(9) -0.0008(9) -0.0023(10) C12 0.0211(11) 0.0228(11) 0.0257(11) -0.0046(9) 0.0054(9) -0.0031(9) C13 0.0263(12) 0.0214(10) 0.0246(11) 0.0005(8) 0.0077(9) -0.0021(9) C14 0.0234(11) 0.0248(11) 0.0205(10) -0.0023(8) 0.0017(8) 0.0008(9) C15 0.0279(13) 0.0288(11) 0.0233(11) -0.0005(9) 0.0058(9) 0.0001(10) _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 C1 1.895(2) . ? F1 C10 1.343(3) . ? F2 C11 1.335(3) . ? F3 C13 1.334(2) . ? F4 C14 1.344(3) . ? N1 C15 1.146(3) . ? C1 C2 1.380(3) . ? C1 C6 1.389(3) . ? C2 C3 1.386(3) . ? C2 H2A 0.9500 . ? C3 C4 1.396(3) . ? C3 H3A 0.9500 . ? C4 C5 1.397(3) . ? C4 C7 1.467(3) . ? C5 C6 1.387(3) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.334(3) . ? C7 H7A 0.9500 . ? C8 C9 1.457(3) . ? C8 H8A 0.9500 . ? C9 C10 1.393(3) . ? C9 C14 1.401(3) . ? C10 C11 1.375(3) . ? C11 C12 1.388(3) . ? C12 C13 1.389(3) . ? C12 C15 1.436(3) . ? C13 C14 1.368(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_3 _geom_angle_publ_flag C2 C1 C6 121.9(2) . . ? C2 C1 Br1 118.63(16) . . ? C6 C1 Br1 119.48(17) . . ? C1 C2 C3 118.4(2) . . ? C1 C2 H2A 120.8 . . ? C3 C2 H2A 120.8 . . ? C2 C3 C4 121.6(2) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C3 C4 C5 118.3(2) . . ? C3 C4 C7 118.1(2) . . ? C5 C4 C7 123.6(2) . . ? C6 C5 C4 121.1(2) . . ? C6 C5 H5A 119.5 . . ? C4 C5 H5A 119.5 . . ? C5 C6 C1 118.7(2) . . ? C5 C6 H6A 120.7 . . ? C1 C6 H6A 120.7 . . ? C8 C7 C4 125.5(2) . . ? C8 C7 H7A 117.2 . . ? C4 C7 H7A 117.2 . . ? C7 C8 C9 126.8(2) . . ? C7 C8 H8A 116.6 . . ? C9 C8 H8A 116.6 . . ? C10 C9 C14 114.7(2) . . ? C10 C9 C8 126.3(2) . . ? C14 C9 C8 119.0(2) . . ? F1 C10 C11 116.7(2) . . ? F1 C10 C9 120.5(2) . . ? C11 C10 C9 122.8(2) . . ? F2 C11 C10 119.7(2) . . ? F2 C11 C12 118.9(2) . . ? C10 C11 C12 121.4(2) . . ? C11 C12 C13 116.9(2) . . ? C11 C12 C15 120.9(2) . . ? C13 C12 C15 122.2(2) . . ? F3 C13 C14 119.4(2) . . ? F3 C13 C12 119.6(2) . . ? C14 C13 C12 121.0(2) . . ? F4 C14 C13 117.7(2) . . ? F4 C14 C9 119.12(19) . . ? C13 C14 C9 123.2(2) . . ? N1 C15 C12 178.8(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 C6 C1 C2 C3 -1.6(3) . . . . ? Br1 C1 C2 C3 178.88(18) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C2 C3 C4 C5 2.1(4) . . . . ? C2 C3 C4 C7 -178.0(2) . . . . ? C3 C4 C5 C6 -1.5(3) . . . . ? C7 C4 C5 C6 178.6(2) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? C2 C1 C6 C5 2.2(3) . . . . ? Br1 C1 C6 C5 -178.29(17) . . . . ? C3 C4 C7 C8 175.9(2) . . . . ? C5 C4 C7 C8 -4.2(4) . . . . ? C4 C7 C8 C9 -179.4(2) . . . . ? C7 C8 C9 C10 11.8(4) . . . . ? C7 C8 C9 C14 -170.2(2) . . . . ? C14 C9 C10 F1 -177.1(2) . . . . ? C8 C9 C10 F1 1.1(4) . . . . ? C14 C9 C10 C11 0.5(3) . . . . ? C8 C9 C10 C11 178.6(2) . . . . ? F1 C10 C11 F2 -2.0(3) . . . . ? C9 C10 C11 F2 -179.6(2) . . . . ? F1 C10 C11 C12 177.3(2) . . . . ? C9 C10 C11 C12 -0.3(4) . . . . ? F2 C11 C12 C13 179.4(2) . . . . ? C10 C11 C12 C13 0.0(3) . . . . ? F2 C11 C12 C15 -0.3(3) . . . . ? C10 C11 C12 C15 -179.7(2) . . . . ? C11 C12 C13 F3 179.8(2) . . . . ? C15 C12 C13 F3 -0.5(3) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C15 C12 C13 C14 179.6(2) . . . . ? F3 C13 C14 F4 0.1(3) . . . . ? C12 C13 C14 F4 180.0(2) . . . . ? F3 C13 C14 C9 -179.6(2) . . . . ? C12 C13 C14 C9 0.3(4) . . . . ? C10 C9 C14 F4 179.9(2) . . . . ? C8 C9 C14 F4 1.6(3) . . . . ? C10 C9 C14 C13 -0.5(3) . . . . ? C8 C9 C14 C13 -178.7(2) . . . . ? C11 C12 C15 N1 -1(13) . . . . ? C13 C12 C15 N1 179(100) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.06 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.376 _refine_diff_density_min -0.498 _refine_diff_density_rms 0.081 # Attachment 'CF8B.CIF' data_CF8B _database_code_depnum_ccdc_archive 'CCDC 291489' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H2 Br F8 N' _chemical_formula_sum 'C15 H2 Br F8 N' _chemical_formula_weight 428.09 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' Br Br -0.2901 2.4595 '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' N N 0.0061 0.0033 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2037(17) _cell_length_b 8.0870(18) _cell_length_c 13.661(3) _cell_angle_alpha 81.226(18) _cell_angle_beta 79.789(18) _cell_angle_gamma 62.434(16) _cell_volume 692.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 6301 _cell_measurement_theta_min 1.50 _cell_measurement_theta_max 24.90 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.054 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 3.065 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.067 _exptl_absorpt_correction_T_max 0.509 _exptl_absorpt_process_details 'DIFABS (Platon, Spek 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'STOE IPDS-2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6252 _diffrn_reflns_av_R_equivalents 0.0816 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 24.65 _reflns_number_total 2349 _reflns_number_gt 1814 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'X-Area V1.17 (STOE & Cie GmbH, 2002)' _computing_cell_refinement 'X-Area V1.17' _computing_data_reduction 'X-RED32 V1.04 (STOE & Cie GmbH, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _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^)+(0.0760P)^2^] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2349 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1248 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 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 0.71967(8) 0.44296(7) -0.31559(4) 0.0572(2) Uani 1 1 d . . . F1 F 0.7452(5) 0.8117(4) -0.3148(2) 0.0563(7) Uani 1 1 d . . . F2 F 0.7593(4) 0.9708(4) -0.1622(2) 0.0502(6) Uani 1 1 d . . . F3 F 0.7367(5) 0.4661(4) 0.0579(2) 0.0527(7) Uani 1 1 d . . . F4 F 0.7230(5) 0.3096(4) -0.0944(2) 0.0573(7) Uani 1 1 d . . . F5 F 0.8147(5) 1.1056(4) 0.1068(2) 0.0556(7) Uani 1 1 d . . . F6 F 0.8199(5) 1.2674(4) 0.2594(2) 0.0554(7) Uani 1 1 d . . . F7 F 0.7071(5) 0.8112(4) 0.4842(2) 0.0646(8) Uani 1 1 d . . . F8 F 0.7023(5) 0.6450(4) 0.3311(2) 0.0593(7) Uani 1 1 d . . . N1 N 0.7581(8) 1.2106(7) 0.5225(4) 0.0720(13) Uani 1 1 d . . . C1 C 0.7307(7) 0.5570(7) -0.2082(4) 0.0473(11) Uani 1 1 d . . . C2 C 0.7410(8) 0.7254(7) -0.2225(4) 0.0482(11) Uani 1 1 d . . . C3 C 0.7492(7) 0.8073(6) -0.1422(4) 0.0444(10) Uani 1 1 d . . . C4 C 0.7467(7) 0.7270(6) -0.0448(3) 0.0428(10) Uani 1 1 d . . . C5 C 0.7355(7) 0.5581(7) -0.0331(3) 0.0444(10) Uani 1 1 d . . . C6 C 0.7299(7) 0.4735(6) -0.1122(4) 0.0464(11) Uani 1 1 d . . . C7 C 0.7577(7) 0.8236(6) 0.0351(4) 0.0444(10) Uani 1 1 d . . . H7 H 0.7781 0.9324 0.0154 0.053 Uiso 1 1 calc R . . C8 C 0.7415(8) 0.7731(7) 0.1335(4) 0.0467(11) Uani 1 1 d . . . H8 H 0.7198 0.6649 0.1534 0.056 Uiso 1 1 calc R . . C9 C 0.7541(7) 0.8692(6) 0.2123(3) 0.0432(10) Uani 1 1 d . . . C10 C 0.7870(7) 1.0286(7) 0.1988(3) 0.0456(11) Uani 1 1 d . . . C11 C 0.7892(7) 1.1146(6) 0.2777(4) 0.0468(11) Uani 1 1 d . . . C12 C 0.7606(8) 1.0446(7) 0.3758(4) 0.0489(11) Uani 1 1 d . . . C13 C 0.7303(8) 0.8856(7) 0.3914(4) 0.0507(11) Uani 1 1 d . . . C14 C 0.7279(8) 0.7997(7) 0.3115(4) 0.0485(11) Uani 1 1 d . . . C15 C 0.7585(8) 1.1393(8) 0.4586(4) 0.0545(12) 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 Br1 0.0612(4) 0.0604(3) 0.0577(4) -0.0145(2) -0.0106(2) -0.0296(3) F1 0.0726(19) 0.0620(17) 0.0409(15) 0.0024(13) -0.0089(13) -0.0370(16) F2 0.0636(17) 0.0470(15) 0.0493(15) 0.0011(12) -0.0045(13) -0.0348(14) F3 0.0705(18) 0.0490(15) 0.0486(16) -0.0015(12) -0.0055(13) -0.0367(14) F4 0.0744(19) 0.0478(15) 0.0634(18) -0.0067(13) -0.0077(15) -0.0386(15) F5 0.085(2) 0.0537(16) 0.0439(16) 0.0033(12) -0.0075(14) -0.0465(16) F6 0.0705(18) 0.0513(16) 0.0582(17) -0.0055(13) -0.0059(14) -0.0393(15) F7 0.091(2) 0.079(2) 0.0386(16) -0.0022(14) -0.0033(15) -0.0533(19) F8 0.087(2) 0.0585(17) 0.0494(16) 0.0012(13) -0.0041(15) -0.0503(17) N1 0.081(3) 0.078(3) 0.067(3) -0.018(3) -0.009(3) -0.040(3) C1 0.046(3) 0.049(3) 0.049(3) -0.009(2) -0.010(2) -0.021(2) C2 0.050(3) 0.050(3) 0.049(3) -0.004(2) -0.008(2) -0.026(2) C3 0.044(2) 0.043(2) 0.051(3) -0.004(2) -0.004(2) -0.024(2) C4 0.047(2) 0.043(2) 0.046(3) -0.002(2) -0.004(2) -0.027(2) C5 0.050(3) 0.050(3) 0.039(2) -0.001(2) -0.003(2) -0.029(2) C6 0.050(3) 0.041(2) 0.054(3) -0.007(2) -0.005(2) -0.025(2) C7 0.049(3) 0.041(2) 0.049(3) 0.000(2) -0.004(2) -0.027(2) C8 0.053(3) 0.044(2) 0.052(3) -0.002(2) -0.005(2) -0.030(2) C9 0.046(2) 0.044(2) 0.044(3) -0.004(2) -0.002(2) -0.025(2) C10 0.049(3) 0.048(3) 0.044(3) -0.002(2) -0.005(2) -0.027(2) C11 0.043(3) 0.041(2) 0.061(3) -0.007(2) -0.005(2) -0.022(2) C12 0.050(3) 0.054(3) 0.048(3) -0.007(2) -0.006(2) -0.027(2) C13 0.053(3) 0.061(3) 0.042(3) -0.003(2) -0.001(2) -0.031(3) C14 0.054(3) 0.052(3) 0.049(3) -0.002(2) -0.001(2) -0.034(2) C15 0.055(3) 0.063(3) 0.051(3) -0.005(3) -0.004(2) -0.032(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 1.879(4) . ? F1 C2 1.346(6) . ? F2 C3 1.342(5) . ? F3 C5 1.347(5) . ? F4 C6 1.334(5) . ? F5 C10 1.341(5) . ? F6 C11 1.333(5) . ? F7 C13 1.335(6) . ? F8 C14 1.329(5) . ? N1 C15 1.116(6) . ? C1 C2 1.380(7) . ? C1 C6 1.381(7) . ? C2 C3 1.388(6) . ? C3 C4 1.390(7) . ? C4 C5 1.389(6) . ? C4 C7 1.468(6) . ? C5 C6 1.379(6) . ? C7 C8 1.344(7) . ? C7 H7 0.9500 . ? C8 C9 1.459(6) . ? C8 H8 0.9500 . ? C9 C10 1.395(6) . ? C9 C14 1.401(7) . ? C10 C11 1.375(6) . ? C11 C12 1.392(7) . ? C12 C13 1.381(7) . ? C12 C15 1.455(7) . ? C13 C14 1.386(7) . ? 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 C1 C6 118.0(4) . . ? C2 C1 Br1 121.4(4) . . ? C6 C1 Br1 120.7(3) . . ? F1 C2 C1 120.5(4) . . ? F1 C2 C3 119.0(4) . . ? C1 C2 C3 120.5(5) . . ? F2 C3 C2 117.0(4) . . ? F2 C3 C4 120.3(4) . . ? C2 C3 C4 122.7(4) . . ? C5 C4 C3 115.2(4) . . ? C5 C4 C7 126.1(4) . . ? C3 C4 C7 118.7(4) . . ? F3 C5 C6 116.9(4) . . ? F3 C5 C4 120.1(4) . . ? C6 C5 C4 122.9(4) . . ? F4 C6 C5 118.9(4) . . ? F4 C6 C1 120.4(4) . . ? C5 C6 C1 120.8(4) . . ? C8 C7 C4 126.3(4) . . ? C8 C7 H7 116.8 . . ? C4 C7 H7 116.8 . . ? C7 C8 C9 126.0(4) . . ? C7 C8 H8 117.0 . . ? C9 C8 H8 117.0 . . ? C10 C9 C14 115.7(4) . . ? C10 C9 C8 126.0(4) . . ? C14 C9 C8 118.3(4) . . ? F5 C10 C11 117.3(4) . . ? F5 C10 C9 120.4(4) . . ? C11 C10 C9 122.3(4) . . ? F6 C11 C10 119.2(4) . . ? F6 C11 C12 119.7(4) . . ? C10 C11 C12 121.1(4) . . ? C13 C12 C11 117.9(4) . . ? C13 C12 C15 121.5(4) . . ? C11 C12 C15 120.6(4) . . ? F7 C13 C12 119.8(4) . . ? F7 C13 C14 119.5(4) . . ? C12 C13 C14 120.7(4) . . ? F8 C14 C13 118.0(4) . . ? F8 C14 C9 119.7(4) . . ? C13 C14 C9 122.3(4) . . ? N1 C15 C12 179.4(7) . . ? 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 C6 C1 C2 F1 179.1(4) . . . . ? Br1 C1 C2 F1 -0.6(6) . . . . ? C6 C1 C2 C3 -0.3(7) . . . . ? Br1 C1 C2 C3 -180.0(4) . . . . ? F1 C2 C3 F2 0.5(6) . . . . ? C1 C2 C3 F2 179.9(4) . . . . ? F1 C2 C3 C4 -179.7(4) . . . . ? C1 C2 C3 C4 -0.2(7) . . . . ? F2 C3 C4 C5 179.9(4) . . . . ? C2 C3 C4 C5 0.0(7) . . . . ? F2 C3 C4 C7 -0.6(7) . . . . ? C2 C3 C4 C7 179.5(4) . . . . ? C3 C4 C5 F3 178.6(4) . . . . ? C7 C4 C5 F3 -0.9(7) . . . . ? C3 C4 C5 C6 0.8(7) . . . . ? C7 C4 C5 C6 -178.6(4) . . . . ? F3 C5 C6 F4 1.0(6) . . . . ? C4 C5 C6 F4 178.8(4) . . . . ? F3 C5 C6 C1 -179.2(4) . . . . ? C4 C5 C6 C1 -1.4(7) . . . . ? C2 C1 C6 F4 -179.1(4) . . . . ? Br1 C1 C6 F4 0.6(6) . . . . ? C2 C1 C6 C5 1.1(7) . . . . ? Br1 C1 C6 C5 -179.2(4) . . . . ? C5 C4 C7 C8 -5.8(8) . . . . ? C3 C4 C7 C8 174.8(5) . . . . ? C4 C7 C8 C9 179.5(4) . . . . ? C7 C8 C9 C10 -0.6(8) . . . . ? C7 C8 C9 C14 178.2(5) . . . . ? C14 C9 C10 F5 179.7(4) . . . . ? C8 C9 C10 F5 -1.4(7) . . . . ? C14 C9 C10 C11 -1.3(7) . . . . ? C8 C9 C10 C11 177.6(5) . . . . ? F5 C10 C11 F6 -0.5(7) . . . . ? C9 C10 C11 F6 -179.5(4) . . . . ? F5 C10 C11 C12 179.7(4) . . . . ? C9 C10 C11 C12 0.7(8) . . . . ? F6 C11 C12 C13 -179.7(4) . . . . ? C10 C11 C12 C13 0.1(7) . . . . ? F6 C11 C12 C15 1.6(7) . . . . ? C10 C11 C12 C15 -178.6(4) . . . . ? C11 C12 C13 F7 178.5(4) . . . . ? C15 C12 C13 F7 -2.8(8) . . . . ? C11 C12 C13 C14 -0.3(8) . . . . ? C15 C12 C13 C14 178.5(5) . . . . ? F7 C13 C14 F8 0.0(7) . . . . ? C12 C13 C14 F8 178.7(4) . . . . ? F7 C13 C14 C9 -179.2(4) . . . . ? C12 C13 C14 C9 -0.4(8) . . . . ? C10 C9 C14 F8 -177.9(4) . . . . ? C8 C9 C14 F8 3.1(7) . . . . ? C10 C9 C14 C13 1.2(7) . . . . ? C8 C9 C14 C13 -177.8(5) . . . . ? C13 C12 C15 N1 55(65) . . . . ? C11 C12 C15 N1 -126(64) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C7 H7 F2 0.9500 2.4200 2.776(6) 102.00 . ? C7 H7 F5 0.9500 2.1400 2.832(6) 129.00 . ? C8 H8 F3 0.9500 2.1700 2.847(6) 127.00 . ? C8 H8 F8 0.9500 2.3900 2.754(6) 102.00 . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.65 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.486 _refine_diff_density_min -1.018 _refine_diff_density_rms 0.086 # Attachment 'CH4F4B.CIF' data_CH4F4B _database_code_depnum_ccdc_archive 'CCDC 291490' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H6 Br F4 N' _chemical_formula_sum 'C15 H6 Br F4 N' _chemical_formula_weight 356.12 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' Br Br -0.2901 2.4595 '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' N N 0.0061 0.0033 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8616(10) _cell_length_b 8.3583(11) _cell_length_c 10.1162(14) _cell_angle_alpha 91.004(11) _cell_angle_beta 95.029(11) _cell_angle_gamma 107.029(10) _cell_volume 632.49(15) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 8974 _cell_measurement_theta_min 2.03 _cell_measurement_theta_max 29.60 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.870 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 3.289 _exptl_absorpt_correction_type empircal _exptl_absorpt_correction_T_min 0.052 _exptl_absorpt_correction_T_max 0.477 _exptl_absorpt_process_details 'refined from \DF (DELABS in PLATON; Spek, 2003' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'STOE IPDS-2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6228 _diffrn_reflns_av_R_equivalents 0.0629 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 29.63 _reflns_number_total 2534 _reflns_number_gt 2299 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'X-Area V2.1 (STOE, 2003)' _computing_cell_refinement 'X-Area V2.1' _computing_data_reduction 'X-RED32 V1.05 (STOE, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _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^)+(0.0761P)^2^+0.7950P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2534 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1379 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 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 0.42646(6) 0.02873(5) 0.26799(4) 0.03922(16) Uani 1 1 d . . . F1 F 0.5836(3) 0.2815(4) 0.5005(3) 0.0427(6) Uani 1 1 d . . . F2 F 0.4256(3) 0.4326(3) 0.6585(3) 0.0402(6) Uani 1 1 d . . . F3 F -0.1328(3) 0.1563(3) 0.4209(2) 0.0370(5) Uani 1 1 d . . . F4 F 0.0281(4) 0.0015(3) 0.2647(3) 0.0390(6) Uani 1 1 d . . . N1 N -0.3747(6) 0.8437(6) 1.1172(5) 0.0539(11) Uani 1 1 d . . . C1 C 0.3110(5) 0.1379(5) 0.3777(4) 0.0338(7) Uani 1 1 d . . . C2 C 0.4064(5) 0.2483(5) 0.4799(4) 0.0344(8) Uani 1 1 d . . . C3 C 0.3211(5) 0.3279(5) 0.5620(4) 0.0332(7) Uani 1 1 d . . . C4 C 0.1376(5) 0.3023(5) 0.5466(4) 0.0322(7) Uani 1 1 d . . . C5 C 0.0446(5) 0.1901(5) 0.4425(4) 0.0321(7) Uani 1 1 d . . . C6 C 0.1277(5) 0.1102(5) 0.3599(4) 0.0316(7) Uani 1 1 d . . . C7 C 0.0383(5) 0.3765(5) 0.6331(4) 0.0342(8) Uani 1 1 d . . . H7 H -0.0904 0.3277 0.6108 0.026(11) Uiso 1 1 d R . . C8 C 0.1058(5) 0.4981(5) 0.7284(4) 0.0359(8) Uani 1 1 d . . . H8 H 0.2418 0.5441 0.7453 0.053(16) Uiso 1 1 d R . . C9 C -0.0009(5) 0.5659(5) 0.8128(4) 0.0334(7) Uani 1 1 d . . . C10 C -0.1871(6) 0.5046(5) 0.8081(4) 0.0370(8) Uani 1 1 d . . . H10 H -0.2529 0.4209 0.7546 0.030(11) Uiso 1 1 d R . . C11 C -0.2802(6) 0.5764(6) 0.8881(4) 0.0378(8) Uani 1 1 d . . . H11 H -0.4068 0.5350 0.8862 0.033(12) Uiso 1 1 d R . . C12 C -0.1896(6) 0.7111(5) 0.9751(4) 0.0356(8) Uani 1 1 d . . . C13 C -0.0036(6) 0.7732(5) 0.9829(4) 0.0370(8) Uani 1 1 d . . . H13 H 0.0507 0.8645 1.0377 0.033(12) Uiso 1 1 d R . . C14 C 0.0880(5) 0.7006(5) 0.9015(4) 0.0359(8) Uani 1 1 d . . . H14 H 0.2219 0.7413 0.9122 0.039(13) Uiso 1 1 d R . . C15 C -0.2920(7) 0.7852(6) 1.0548(5) 0.0420(10) 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 Br1 0.0417(2) 0.0424(2) 0.0380(2) -0.00227(16) 0.01052(16) 0.01771(17) F1 0.0316(11) 0.0533(15) 0.0452(14) -0.0053(12) 0.0031(10) 0.0166(11) F2 0.0321(11) 0.0462(14) 0.0405(13) -0.0112(11) -0.0014(10) 0.0109(10) F3 0.0282(10) 0.0413(12) 0.0405(12) -0.0021(10) 0.0024(9) 0.0092(9) F4 0.0427(13) 0.0377(13) 0.0360(12) -0.0084(10) 0.0025(10) 0.0119(11) N1 0.049(2) 0.060(3) 0.057(2) -0.010(2) 0.0139(19) 0.020(2) C1 0.0373(18) 0.0352(18) 0.0325(17) 0.0013(15) 0.0077(15) 0.0149(15) C2 0.0306(17) 0.0380(19) 0.0364(19) 0.0024(16) 0.0074(15) 0.0119(15) C3 0.0352(18) 0.0318(17) 0.0323(17) -0.0026(15) 0.0025(14) 0.0100(14) C4 0.0320(17) 0.0332(17) 0.0327(17) 0.0030(14) 0.0061(14) 0.0108(14) C5 0.0326(17) 0.0326(17) 0.0330(17) 0.0031(14) 0.0052(14) 0.0116(14) C6 0.0363(18) 0.0323(17) 0.0277(16) -0.0009(14) 0.0035(14) 0.0127(14) C7 0.0323(17) 0.0380(19) 0.0344(18) -0.0005(15) 0.0062(14) 0.0130(15) C8 0.0324(17) 0.040(2) 0.0368(19) -0.0021(16) 0.0087(15) 0.0113(15) C9 0.0393(19) 0.0299(16) 0.0311(17) 0.0000(14) 0.0053(15) 0.0101(14) C10 0.040(2) 0.038(2) 0.0349(19) -0.0060(16) 0.0016(15) 0.0153(16) C11 0.0377(18) 0.041(2) 0.037(2) -0.0012(17) 0.0067(16) 0.0141(16) C12 0.0394(19) 0.0365(19) 0.0328(18) 0.0000(15) 0.0079(15) 0.0130(16) C13 0.042(2) 0.0334(18) 0.0366(19) -0.0031(15) 0.0082(16) 0.0114(16) C14 0.0353(18) 0.0343(18) 0.0361(19) -0.0035(15) 0.0033(15) 0.0077(15) C15 0.046(2) 0.040(2) 0.043(2) -0.0010(18) 0.0088(18) 0.0159(18) _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 C1 1.875(4) . ? F1 C2 1.334(4) . ? F2 C3 1.343(4) . ? F3 C5 1.337(4) . ? F4 C6 1.336(4) . ? N1 C15 1.143(6) . ? C1 C2 1.382(6) . ? C1 C6 1.386(5) . ? C2 C3 1.386(5) . ? C3 C4 1.389(5) . ? C4 C5 1.397(5) . ? C4 C7 1.464(5) . ? C5 C6 1.379(5) . ? C7 C8 1.344(5) . ? C7 H7 0.9775 . ? C8 C9 1.462(5) . ? C8 H8 1.0228 . ? C9 C14 1.398(5) . ? C9 C10 1.398(6) . ? C10 C11 1.377(6) . ? C10 H10 0.8809 . ? C11 C12 1.391(6) . ? C11 H11 0.9511 . ? C12 C13 1.396(6) . ? C12 C15 1.439(6) . ? C13 C14 1.381(5) . ? C13 H13 0.9080 . ? C14 H14 1.0022 . ? 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 C1 C6 117.7(3) . . ? C2 C1 Br1 120.8(3) . . ? C6 C1 Br1 121.4(3) . . ? F1 C2 C1 120.3(4) . . ? F1 C2 C3 118.7(4) . . ? C1 C2 C3 120.9(4) . . ? F2 C3 C2 116.4(4) . . ? F2 C3 C4 121.1(3) . . ? C2 C3 C4 122.5(4) . . ? C3 C4 C5 115.2(3) . . ? C3 C4 C7 125.3(4) . . ? C5 C4 C7 119.4(4) . . ? F3 C5 C6 117.6(3) . . ? F3 C5 C4 119.5(3) . . ? C6 C5 C4 122.9(4) . . ? F4 C6 C5 119.0(4) . . ? F4 C6 C1 120.3(3) . . ? C5 C6 C1 120.6(4) . . ? C8 C7 C4 127.4(4) . . ? C8 C7 H7 122.0 . . ? C4 C7 H7 110.5 . . ? C7 C8 C9 124.8(4) . . ? C7 C8 H8 117.6 . . ? C9 C8 H8 117.5 . . ? C14 C9 C10 118.3(4) . . ? C14 C9 C8 118.2(4) . . ? C10 C9 C8 123.5(3) . . ? C11 C10 C9 120.7(4) . . ? C11 C10 H10 115.5 . . ? C9 C10 H10 123.9 . . ? C10 C11 C12 120.2(4) . . ? C10 C11 H11 121.3 . . ? C12 C11 H11 118.6 . . ? C11 C12 C13 120.3(4) . . ? C11 C12 C15 118.5(4) . . ? C13 C12 C15 121.2(4) . . ? C14 C13 C12 118.9(4) . . ? C14 C13 H13 123.1 . . ? C12 C13 H13 117.9 . . ? C13 C14 C9 121.7(4) . . ? C13 C14 H14 118.1 . . ? C9 C14 H14 120.1 . . ? N1 C15 C12 179.4(6) . . ? 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 C6 C1 C2 F1 -179.1(4) . . . . ? Br1 C1 C2 F1 1.3(6) . . . . ? C6 C1 C2 C3 0.3(6) . . . . ? Br1 C1 C2 C3 -179.4(3) . . . . ? F1 C2 C3 F2 -0.8(6) . . . . ? C1 C2 C3 F2 179.8(4) . . . . ? F1 C2 C3 C4 179.2(4) . . . . ? C1 C2 C3 C4 -0.1(7) . . . . ? F2 C3 C4 C5 -179.9(4) . . . . ? C2 C3 C4 C5 0.1(6) . . . . ? F2 C3 C4 C7 -2.8(7) . . . . ? C2 C3 C4 C7 177.2(4) . . . . ? C3 C4 C5 F3 179.3(4) . . . . ? C7 C4 C5 F3 2.1(6) . . . . ? C3 C4 C5 C6 -0.2(6) . . . . ? C7 C4 C5 C6 -177.5(4) . . . . ? F3 C5 C6 F4 -1.2(6) . . . . ? C4 C5 C6 F4 178.3(4) . . . . ? F3 C5 C6 C1 -179.2(4) . . . . ? C4 C5 C6 C1 0.4(6) . . . . ? C2 C1 C6 F4 -178.3(4) . . . . ? Br1 C1 C6 F4 1.3(5) . . . . ? C2 C1 C6 C5 -0.4(6) . . . . ? Br1 C1 C6 C5 179.2(3) . . . . ? C3 C4 C7 C8 10.3(8) . . . . ? C5 C4 C7 C8 -172.7(4) . . . . ? C4 C7 C8 C9 -179.3(4) . . . . ? C7 C8 C9 C14 -175.6(4) . . . . ? C7 C8 C9 C10 3.6(7) . . . . ? C14 C9 C10 C11 0.6(7) . . . . ? C8 C9 C10 C11 -178.5(4) . . . . ? C9 C10 C11 C12 -0.2(7) . . . . ? C10 C11 C12 C13 -0.7(7) . . . . ? C10 C11 C12 C15 178.6(4) . . . . ? C11 C12 C13 C14 1.0(7) . . . . ? C15 C12 C13 C14 -178.2(4) . . . . ? C12 C13 C14 C9 -0.6(7) . . . . ? C10 C9 C14 C13 -0.3(7) . . . . ? C8 C9 C14 C13 178.9(4) . . . . ? C11 C12 C15 N1 -32(53) . . . . ? C13 C12 C15 N1 148(53) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C7 H7 F3 0.9778 2.3164 2.777(5) 107.85 . ? C8 H8 F2 1.0223 2.1703 2.868(5) 123.82 . ? _diffrn_measured_fraction_theta_max 0.711 _diffrn_reflns_theta_full 29.63 _diffrn_measured_fraction_theta_full 0.711 _refine_diff_density_max 0.574 _refine_diff_density_min -1.294 _refine_diff_density_rms 0.099 # Attachment 'CH8B.CIF' data_CH8B _database_code_depnum_ccdc_archive 'CCDC 291491' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H10 Br N' _chemical_formula_sum 'C15 H10 Br N' _chemical_formula_weight 284.15 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9795(13) _cell_length_b 13.3572(14) _cell_length_c 16.7277(19) _cell_angle_alpha 104.434(9) _cell_angle_beta 104.567(9) _cell_angle_gamma 102.171(9) _cell_volume 1999.0(4) _cell_formula_units_Z 7 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 28929 _cell_measurement_theta_min 1.65 _cell_measurement_theta_max 29.50 _exptl_crystal_description block _exptl_crystal_colour pale_yellow _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.652 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 994 _exptl_absorpt_coefficient_mu 3.571 _exptl_absorpt_correction_type empircal _exptl_absorpt_correction_T_min 0.354 _exptl_absorpt_correction_T_max 0.771 _exptl_absorpt_process_details 'DIFABS (Spek, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'STOE IPDS-2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19932 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.50 _reflns_number_total 7421 _reflns_number_gt 5845 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'X-Area V1.17 (STOE & Cie GmbH, 2002)' _computing_cell_refinement 'X-Area V1.17' _computing_data_reduction 'X-RED32 V1.04 (STOE & Cie GmbH, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; The H-atoms were included in calculated postions and teated as riding atoms using SHELXL default parameters; C-H 0.95 \%A U~iso~(H) = 1.2 x U~eq~(parent C-atom). The data werer limited to 51\% in 2\q for the refinement and the distances C32-C35 and C61-C68 constrained to 1.50 +/- 0.02 \%A, distances C35-N2 and C68-N4 constrained to 1.00 +/- 0.02 \%A, and distance C61-Br1 constrained to 1.90 +/- 0.02 \%A. ; _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^)+(0.0667P)^2^+7.1118P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7421 _refine_ls_number_parameters 550 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0837 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1638 _refine_ls_wR_factor_gt 0.1523 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean <0.001 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 Br4 Br 0.7587(5) 0.1823(3) 0.2180(3) 0.0427(6) Uani 0.50 1 d PD . . C61 C 0.6773(6) 0.1194(5) 0.2988(4) 0.0389(13) Uani 1 1 d D . . C62 C 0.6298(6) 0.0098(5) 0.2778(4) 0.0413(14) Uani 1 1 d . . . H62 H 0.6370 -0.0353 0.2263 0.050 Uiso 1 1 calc R . . C63 C 0.5723(6) -0.0348(5) 0.3305(4) 0.0414(14) Uani 1 1 d . . . H63 H 0.5359 -0.1112 0.3141 0.050 Uiso 1 1 calc R . . C64 C 0.5656(6) 0.0284(5) 0.4073(4) 0.0388(13) Uani 1 1 d . . . C65 C 0.6158(6) 0.1391(5) 0.4281(4) 0.0425(14) Uani 1 1 d . . . H65 H 0.6122 0.1844 0.4808 0.051 Uiso 1 1 calc R . . C66 C 0.6707(6) 0.1845(5) 0.3742(4) 0.0414(14) Uani 1 1 d . . . H66 H 0.7041 0.2609 0.3889 0.050 Uiso 1 1 calc R . . C67 C 0.5039(6) -0.0240(5) 0.4614(4) 0.0407(14) Uani 1 1 d . . . H67 H 0.4652 -0.1004 0.4391 0.049 Uiso 1 1 calc R . . C68 C 0.7304(18) 0.1753(14) 0.2458(10) 0.043(7) Uani 0.50 1 d PD . . Br1 Br -0.13221(7) -0.50800(5) 0.31600(5) 0.0533(2) Uani 1 1 d . . . N1 N 0.2791(7) 0.5790(6) 0.4924(4) 0.0544(15) Uani 1 1 d . . . C1 C -0.0889(7) -0.3569(5) 0.3424(4) 0.0404(13) Uani 1 1 d . . . C2 C -0.1977(7) -0.3108(5) 0.3325(4) 0.0442(14) Uani 1 1 d . . . H2 H -0.2958 -0.3540 0.3118 0.053 Uiso 1 1 calc R . . C3 C -0.1642(7) -0.2022(5) 0.3526(4) 0.0444(15) Uani 1 1 d . . . H3 H -0.2408 -0.1699 0.3462 0.053 Uiso 1 1 calc R . . C4 C -0.0246(7) -0.1367(5) 0.3818(4) 0.0393(13) Uani 1 1 d . . . C5 C 0.0814(7) -0.1880(5) 0.3894(4) 0.0414(14) Uani 1 1 d . . . H5 H 0.1797 -0.1457 0.4081 0.050 Uiso 1 1 calc R . . C6 C 0.0517(7) -0.2954(5) 0.3713(4) 0.0421(14) Uani 1 1 d . . . H6 H 0.1278 -0.3281 0.3786 0.050 Uiso 1 1 calc R . . C7 C 0.0059(7) -0.0205(5) 0.4002(4) 0.0475(15) Uani 1 1 d . . . H7 H -0.0756 0.0065 0.3948 0.057 Uiso 1 1 calc R . . C8 C 0.1340(7) 0.0530(5) 0.4237(4) 0.0475(15) Uani 1 1 d . . . H8 H 0.2160 0.0266 0.4288 0.057 Uiso 1 1 calc R . . C9 C 0.1606(7) 0.1649(5) 0.4418(4) 0.0452(15) Uani 1 1 d . . . C10 C 0.0504(6) 0.2135(5) 0.4344(4) 0.0424(14) Uani 1 1 d . . . H10 H -0.0468 0.1715 0.4206 0.051 Uiso 1 1 calc R . . C11 C 0.0820(7) 0.3206(5) 0.4470(4) 0.0446(14) Uani 1 1 d . . . H11 H 0.0062 0.3536 0.4401 0.054 Uiso 1 1 calc R . . C12 C 0.2234(7) 0.3827(5) 0.4698(4) 0.0439(14) Uani 1 1 d . . . C13 C 0.3318(7) 0.3358(6) 0.4786(4) 0.0485(15) Uani 1 1 d . . . H13 H 0.4295 0.3779 0.4940 0.058 Uiso 1 1 calc R . . C14 C 0.2990(7) 0.2291(6) 0.4652(5) 0.0555(18) Uani 1 1 d . . . H14 H 0.3756 0.1968 0.4722 0.067 Uiso 1 1 calc R . . C15 C 0.2587(8) 0.5021(8) 0.4835(4) 0.0551(19) Uani 1 1 d . . . Br2 Br 0.01084(8) -0.39934(5) 0.14210(5) 0.0524(2) Uani 1 1 d . . . N2 N 0.4024(6) 0.6811(4) 0.3236(4) 0.0316(13) Uani 1 1 d D . . C21 C 0.0480(6) -0.2477(4) 0.1677(4) 0.0361(12) Uani 1 1 d . . . C22 C -0.0645(6) -0.2048(5) 0.1604(4) 0.0396(13) Uani 1 1 d . . . H22 H -0.1611 -0.2498 0.1430 0.048 Uiso 1 1 calc R . . C23 C -0.0360(6) -0.0961(5) 0.1785(4) 0.0384(13) Uani 1 1 d . . . H23 H -0.1140 -0.0653 0.1742 0.046 Uiso 1 1 calc R . . C24 C 0.1020(6) -0.0298(5) 0.2029(4) 0.0354(12) Uani 1 1 d . . . C25 C 0.2115(6) -0.0767(5) 0.2098(4) 0.0416(14) Uani 1 1 d . . . H25 H 0.3083 -0.0323 0.2269 0.050 Uiso 1 1 calc R . . C26 C 0.1865(6) -0.1839(5) 0.1931(4) 0.0415(14) Uani 1 1 d . . . H26 H 0.2646 -0.2147 0.1990 0.050 Uiso 1 1 calc R . . C27 C 0.1253(6) 0.0860(4) 0.2209(4) 0.0353(12) Uani 1 1 d . . . H27 H 0.0436 0.1121 0.2200 0.042 Uiso 1 1 calc R . . C28 C 0.2497(6) 0.1572(4) 0.2381(4) 0.0372(12) Uani 1 1 d . . . H28 H 0.3304 0.1299 0.2385 0.045 Uiso 1 1 calc R . . C29 C 0.2780(6) 0.2724(4) 0.2565(4) 0.0344(12) Uani 1 1 d . . . C30 C 0.1698(6) 0.3229(5) 0.2465(4) 0.0372(12) Uani 1 1 d . . . H30 H 0.0713 0.2808 0.2267 0.045 Uiso 1 1 calc R . . C31 C 0.2026(6) 0.4307(5) 0.2646(4) 0.0390(13) Uani 1 1 d . . . H31 H 0.1269 0.4638 0.2572 0.047 Uiso 1 1 calc R . . C32 C 0.3435(7) 0.4936(4) 0.2934(4) 0.0370(13) Uani 1 1 d D . . C33 C 0.4526(6) 0.4449(5) 0.3030(4) 0.0385(13) Uani 1 1 d . . . H33 H 0.5509 0.4875 0.3233 0.046 Uiso 1 1 calc R . . C34 C 0.4192(6) 0.3358(5) 0.2832(4) 0.0411(13) Uani 1 1 d . . . H34 H 0.4948 0.3025 0.2880 0.049 Uiso 1 1 calc R . . C35 C 0.3822(8) 0.6187(7) 0.3145(4) 0.051(2) Uani 1 1 d D . . Br3 Br 0.13403(7) -0.33153(5) -0.04661(5) 0.04716(19) Uani 1 1 d . . . N3 N 0.5776(6) 0.7586(4) 0.1518(3) 0.0435(12) Uani 1 1 d . . . C41 C 0.2069(6) -0.1809(4) -0.0112(4) 0.0355(12) Uani 1 1 d . . . C42 C 0.1152(6) -0.1218(5) -0.0326(4) 0.0365(12) Uani 1 1 d . . . H42 H 0.0154 -0.1564 -0.0638 0.044 Uiso 1 1 calc R . . C43 C 0.1697(6) -0.0131(4) -0.0084(4) 0.0367(12) Uani 1 1 d . . . H43 H 0.1068 0.0285 -0.0232 0.044 Uiso 1 1 calc R . . C44 C 0.3126(6) 0.0383(5) 0.0367(4) 0.0365(12) Uani 1 1 d . . . C45 C 0.3999(7) -0.0239(5) 0.0586(4) 0.0411(13) Uani 1 1 d . . . H45 H 0.4994 0.0103 0.0908 0.049 Uiso 1 1 calc R . . C46 C 0.3478(7) -0.1330(5) 0.0354(4) 0.0409(13) Uani 1 1 d . . . H46 H 0.4095 -0.1748 0.0518 0.049 Uiso 1 1 calc R . . C47 C 0.3778(6) 0.1540(5) 0.0612(4) 0.0378(13) Uani 1 1 d . . . H47 H 0.4788 0.1815 0.0914 0.045 Uiso 1 1 calc R . . C48 C 0.3083(7) 0.2245(4) 0.0450(4) 0.0374(13) Uani 1 1 d . . . H48 H 0.2070 0.1972 0.0154 0.045 Uiso 1 1 calc R . . C49 C 0.3728(6) 0.3389(4) 0.0682(4) 0.0343(12) Uani 1 1 d . . . C50 C 0.2825(7) 0.4038(5) 0.0611(4) 0.0394(13) Uani 1 1 d . . . H50 H 0.1807 0.3716 0.0403 0.047 Uiso 1 1 calc R . . C51 C 0.3357(6) 0.5119(5) 0.0829(4) 0.0372(12) Uani 1 1 d . . . H51 H 0.2717 0.5553 0.0783 0.045 Uiso 1 1 calc R . . C52 C 0.4816(6) 0.5590(4) 0.1114(4) 0.0330(12) Uani 1 1 d . . . C53 C 0.5743(6) 0.4967(5) 0.1183(4) 0.0401(13) Uani 1 1 d . . . H53 H 0.6759 0.5296 0.1378 0.048 Uiso 1 1 calc R . . C54 C 0.5203(6) 0.3880(4) 0.0971(4) 0.0389(13) Uani 1 1 d . . . H54 H 0.5848 0.3451 0.1022 0.047 Uiso 1 1 calc R . . C55 C 0.5388(6) 0.6752(6) 0.1343(4) 0.0394(13) Uani 1 1 d . . . N4 N 0.785(4) 0.207(2) 0.213(2) 0.042(7) Uani 0.50 1 d PD . . 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 Br4 0.0347(17) 0.0509(19) 0.0435(16) 0.0176(13) 0.0155(10) 0.0078(14) C61 0.029(3) 0.040(3) 0.044(3) 0.013(3) 0.005(3) 0.012(2) C62 0.033(3) 0.041(3) 0.041(3) 0.005(3) 0.002(3) 0.016(2) C63 0.034(3) 0.036(3) 0.046(4) 0.007(3) 0.001(3) 0.013(2) C64 0.026(3) 0.039(3) 0.043(3) 0.006(3) 0.003(2) 0.009(2) C65 0.036(3) 0.041(3) 0.045(4) 0.011(3) 0.002(3) 0.015(3) C66 0.030(3) 0.035(3) 0.047(4) 0.005(3) -0.001(3) 0.012(2) C67 0.034(3) 0.036(3) 0.046(3) 0.009(3) 0.002(3) 0.014(2) C68 0.009(7) 0.057(11) 0.033(11) -0.031(9) -0.005(6) 0.017(7) Br1 0.0462(4) 0.0475(4) 0.0716(5) 0.0280(3) 0.0189(3) 0.0144(3) N1 0.063(4) 0.059(4) 0.039(3) 0.007(3) 0.012(3) 0.027(3) C1 0.039(3) 0.048(3) 0.040(3) 0.020(3) 0.014(3) 0.016(3) C2 0.033(3) 0.060(4) 0.047(4) 0.026(3) 0.014(3) 0.017(3) C3 0.045(4) 0.060(4) 0.043(4) 0.026(3) 0.017(3) 0.030(3) C4 0.043(3) 0.048(3) 0.030(3) 0.010(2) 0.010(3) 0.023(3) C5 0.036(3) 0.047(3) 0.038(3) 0.009(3) 0.007(3) 0.017(3) C6 0.042(3) 0.048(3) 0.044(3) 0.018(3) 0.015(3) 0.022(3) C7 0.042(3) 0.043(3) 0.047(4) 0.006(3) 0.004(3) 0.014(3) C8 0.042(4) 0.051(4) 0.051(4) 0.016(3) 0.014(3) 0.017(3) C9 0.038(3) 0.047(3) 0.040(3) 0.000(3) 0.006(3) 0.015(3) C10 0.032(3) 0.055(4) 0.034(3) 0.006(3) 0.003(2) 0.017(3) C11 0.044(3) 0.051(4) 0.039(3) 0.016(3) 0.008(3) 0.018(3) C12 0.043(3) 0.060(4) 0.029(3) 0.016(3) 0.011(3) 0.014(3) C13 0.039(3) 0.060(4) 0.042(4) 0.009(3) 0.015(3) 0.012(3) C14 0.035(3) 0.075(5) 0.048(4) 0.008(3) 0.008(3) 0.022(3) C15 0.040(4) 0.099(6) 0.027(3) 0.025(4) 0.011(3) 0.016(4) Br2 0.0600(4) 0.0398(3) 0.0561(4) 0.0153(3) 0.0198(3) 0.0106(3) N2 0.026(3) 0.043(3) 0.033(3) 0.023(3) 0.009(2) 0.013(3) C21 0.036(3) 0.038(3) 0.037(3) 0.017(2) 0.014(3) 0.007(2) C22 0.034(3) 0.041(3) 0.042(3) 0.014(3) 0.012(3) 0.006(2) C23 0.032(3) 0.044(3) 0.042(3) 0.016(3) 0.013(3) 0.011(2) C24 0.034(3) 0.041(3) 0.032(3) 0.014(2) 0.009(2) 0.012(2) C25 0.030(3) 0.042(3) 0.054(4) 0.020(3) 0.011(3) 0.008(2) C26 0.033(3) 0.044(3) 0.052(4) 0.021(3) 0.012(3) 0.014(3) C27 0.037(3) 0.040(3) 0.034(3) 0.017(2) 0.012(2) 0.014(2) C28 0.039(3) 0.037(3) 0.039(3) 0.014(2) 0.013(3) 0.014(2) C29 0.036(3) 0.038(3) 0.029(3) 0.013(2) 0.009(2) 0.010(2) C30 0.036(3) 0.042(3) 0.034(3) 0.012(2) 0.010(2) 0.010(2) C31 0.037(3) 0.041(3) 0.036(3) 0.009(2) 0.009(3) 0.015(3) C32 0.044(3) 0.033(3) 0.036(3) 0.014(2) 0.014(3) 0.010(2) C33 0.029(3) 0.040(3) 0.045(3) 0.017(3) 0.010(3) 0.007(2) C34 0.035(3) 0.042(3) 0.048(4) 0.018(3) 0.014(3) 0.013(3) C35 0.021(3) 0.109(7) 0.018(3) 0.013(5) 0.005(2) 0.021(5) Br3 0.0482(4) 0.0337(3) 0.0586(4) 0.0148(3) 0.0161(3) 0.0112(3) N3 0.041(3) 0.043(3) 0.042(3) 0.010(2) 0.005(2) 0.016(2) C41 0.041(3) 0.033(3) 0.034(3) 0.011(2) 0.016(3) 0.010(2) C42 0.031(3) 0.041(3) 0.036(3) 0.011(2) 0.011(2) 0.009(2) C43 0.040(3) 0.038(3) 0.037(3) 0.012(2) 0.016(3) 0.016(2) C44 0.040(3) 0.039(3) 0.034(3) 0.015(2) 0.014(3) 0.013(2) C45 0.039(3) 0.040(3) 0.043(3) 0.018(3) 0.008(3) 0.007(2) C46 0.041(3) 0.043(3) 0.043(3) 0.021(3) 0.009(3) 0.017(3) C47 0.036(3) 0.040(3) 0.038(3) 0.015(3) 0.012(3) 0.008(2) C48 0.041(3) 0.035(3) 0.038(3) 0.012(2) 0.017(3) 0.010(2) C49 0.035(3) 0.037(3) 0.032(3) 0.012(2) 0.013(2) 0.009(2) C50 0.037(3) 0.039(3) 0.042(3) 0.015(3) 0.012(3) 0.010(2) C51 0.033(3) 0.040(3) 0.041(3) 0.013(3) 0.012(3) 0.014(2) C52 0.039(3) 0.032(3) 0.030(3) 0.011(2) 0.013(2) 0.013(2) C53 0.033(3) 0.040(3) 0.043(3) 0.010(3) 0.010(3) 0.008(2) C54 0.038(3) 0.033(3) 0.044(3) 0.011(2) 0.010(3) 0.015(2) C55 0.032(3) 0.055(4) 0.033(3) 0.015(3) 0.008(2) 0.018(3) N4 0.037(14) 0.032(12) 0.053(11) 0.019(7) 0.013(8) -0.001(9) _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 Br4 C68 0.618(13) . ? Br4 C61 2.006(7) . ? C61 C62 1.363(8) . ? C61 C66 1.368(9) . ? C61 C68 1.422(14) . ? C62 C63 1.353(9) . ? C62 H62 0.9500 . ? C63 C64 1.377(9) . ? C63 H63 0.9500 . ? C64 C65 1.379(8) . ? C64 C67 1.450(9) . ? C65 C66 1.366(9) . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? C67 C67 1.319(12) 2_656 ? C67 H67 0.9500 . ? C68 N4 0.964(19) . ? Br1 C1 1.883(6) . ? N1 C15 0.969(9) . ? C1 C2 1.352(8) . ? C1 C6 1.361(9) . ? C2 C3 1.351(9) . ? C2 H2 0.9500 . ? C3 C4 1.370(9) . ? C3 H3 0.9500 . ? C4 C5 1.374(8) . ? C4 C7 1.453(9) . ? C5 C6 1.340(9) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.333(9) . ? C7 H7 0.9500 . ? C8 C9 1.401(9) . ? C8 H8 0.9500 . ? C9 C14 1.363(9) . ? C9 C10 1.385(8) . ? C10 C11 1.348(9) . ? C10 H10 0.9500 . ? C11 C12 1.379(9) . ? C11 H11 0.9500 . ? C12 C13 1.355(9) . ? C12 C15 1.504(12) . ? C13 C14 1.340(10) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? Br2 C21 1.896(6) . ? N2 C35 0.780(8) . ? C21 C26 1.358(8) . ? C21 C22 1.358(8) . ? C22 C23 1.357(8) . ? C22 H22 0.9500 . ? C23 C24 1.368(8) . ? C23 H23 0.9500 . ? C24 C25 1.365(8) . ? C24 C27 1.455(8) . ? C25 C26 1.343(8) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.309(8) . ? C27 H27 0.9500 . ? C28 C29 1.441(8) . ? C28 H28 0.9500 . ? C29 C34 1.376(8) . ? C29 C30 1.386(8) . ? C30 C31 1.345(8) . ? C30 H30 0.9500 . ? C31 C32 1.369(8) . ? C31 H31 0.9500 . ? C32 C33 1.377(8) . ? C32 C35 1.560(10) . ? C33 C34 1.358(8) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? Br3 C41 1.870(5) . ? N3 C55 1.037(8) . ? C41 C46 1.348(8) . ? C41 C42 1.367(8) . ? C42 C43 1.354(8) . ? C42 H42 0.9500 . ? C43 C44 1.365(8) . ? C43 H43 0.9500 . ? C44 C45 1.371(8) . ? C44 C47 1.452(8) . ? C45 C46 1.357(8) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C47 C48 1.322(8) . ? C47 H47 0.9500 . ? C48 C49 1.436(8) . ? C48 H48 0.9500 . ? C49 C50 1.380(8) . ? C49 C54 1.381(8) . ? C50 C51 1.349(8) . ? C50 H50 0.9500 . ? C51 C52 1.363(8) . ? C51 H51 0.9500 . ? C52 C53 1.370(8) . ? C52 C55 1.450(9) . ? C53 C54 1.358(8) . ? C53 H53 0.9500 . ? C54 H54 0.9500 . ? 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 C68 Br4 C61 16.0(16) . . ? C62 C61 C66 120.2(6) . . ? C62 C61 C68 125.0(8) . . ? C66 C61 C68 114.8(8) . . ? C62 C61 Br4 118.8(5) . . ? C66 C61 Br4 121.1(5) . . ? C68 C61 Br4 6.9(7) . . ? C63 C62 C61 120.0(6) . . ? C63 C62 H62 120.0 . . ? C61 C62 H62 120.0 . . ? C62 C63 C64 121.3(6) . . ? C62 C63 H63 119.3 . . ? C64 C63 H63 119.3 . . ? C63 C64 C65 117.9(6) . . ? C63 C64 C67 118.8(5) . . ? C65 C64 C67 123.2(6) . . ? C66 C65 C64 121.0(6) . . ? C66 C65 H65 119.5 . . ? C64 C65 H65 119.5 . . ? C65 C66 C61 119.6(6) . . ? C65 C66 H66 120.2 . . ? C61 C66 H66 120.2 . . ? C67 C67 C64 126.5(7) 2_656 . ? C67 C67 H67 116.7 2_656 . ? C64 C67 H67 116.7 . . ? Br4 C68 N4 16(2) . . ? Br4 C68 C61 157(2) . . ? N4 C68 C61 167(4) . . ? C2 C1 C6 120.8(6) . . ? C2 C1 Br1 119.7(5) . . ? C6 C1 Br1 119.6(4) . . ? C3 C2 C1 118.7(6) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 122.8(6) . . ? C2 C3 H3 118.6 . . ? C4 C3 H3 118.6 . . ? C3 C4 C5 115.9(6) . . ? C3 C4 C7 120.8(5) . . ? C5 C4 C7 123.2(6) . . ? C6 C5 C4 122.6(6) . . ? C6 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? C5 C6 C1 119.1(6) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? C8 C7 C4 128.1(6) . . ? C8 C7 H7 115.9 . . ? C4 C7 H7 115.9 . . ? C7 C8 C9 127.0(6) . . ? C7 C8 H8 116.5 . . ? C9 C8 H8 116.5 . . ? C14 C9 C10 118.0(6) . . ? C14 C9 C8 119.6(6) . . ? C10 C9 C8 122.4(6) . . ? C11 C10 C9 119.6(6) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.6(6) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 120.0(6) . . ? C13 C12 C15 119.4(6) . . ? C11 C12 C15 120.6(6) . . ? C14 C13 C12 118.9(7) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C9 122.9(6) . . ? C13 C14 H14 118.6 . . ? C9 C14 H14 118.6 . . ? N1 C15 C12 178.6(9) . . ? C26 C21 C22 121.2(5) . . ? C26 C21 Br2 119.5(4) . . ? C22 C21 Br2 119.3(4) . . ? C23 C22 C21 118.5(5) . . ? C23 C22 H22 120.8 . . ? C21 C22 H22 120.8 . . ? C22 C23 C24 121.8(6) . . ? C22 C23 H23 119.1 . . ? C24 C23 H23 119.1 . . ? C25 C24 C23 117.4(5) . . ? C25 C24 C27 123.4(5) . . ? C23 C24 C27 119.2(5) . . ? C26 C25 C24 122.0(6) . . ? C26 C25 H25 119.0 . . ? C24 C25 H25 119.0 . . ? C25 C26 C21 119.1(6) . . ? C25 C26 H26 120.5 . . ? C21 C26 H26 120.5 . . ? C28 C27 C24 125.3(5) . . ? C28 C27 H27 117.3 . . ? C24 C27 H27 117.3 . . ? C27 C28 C29 127.2(6) . . ? C27 C28 H28 116.4 . . ? C29 C28 H28 116.4 . . ? C34 C29 C30 117.9(5) . . ? C34 C29 C28 118.7(5) . . ? C30 C29 C28 123.4(5) . . ? C31 C30 C29 120.8(6) . . ? C31 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? C30 C31 C32 121.0(6) . . ? C30 C31 H31 119.5 . . ? C32 C31 H31 119.5 . . ? C31 C32 C33 119.1(5) . . ? C31 C32 C35 121.2(5) . . ? C33 C32 C35 119.6(5) . . ? C34 C33 C32 119.8(5) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? C33 C34 C29 121.4(6) . . ? C33 C34 H34 119.3 . . ? C29 C34 H34 119.3 . . ? N2 C35 C32 178.0(11) . . ? C46 C41 C42 121.4(5) . . ? C46 C41 Br3 119.5(4) . . ? C42 C41 Br3 119.1(4) . . ? C43 C42 C41 118.6(5) . . ? C43 C42 H42 120.7 . . ? C41 C42 H42 120.7 . . ? C42 C43 C44 121.7(5) . . ? C42 C43 H43 119.1 . . ? C44 C43 H43 119.1 . . ? C43 C44 C45 117.7(5) . . ? C43 C44 C47 124.0(5) . . ? C45 C44 C47 118.3(5) . . ? C46 C45 C44 121.7(6) . . ? C46 C45 H45 119.1 . . ? C44 C45 H45 119.1 . . ? C41 C46 C45 118.8(5) . . ? C41 C46 H46 120.6 . . ? C45 C46 H46 120.6 . . ? C48 C47 C44 125.5(6) . . ? C48 C47 H47 117.3 . . ? C44 C47 H47 117.3 . . ? C47 C48 C49 125.6(6) . . ? C47 C48 H48 117.2 . . ? C49 C48 H48 117.2 . . ? C50 C49 C54 117.8(5) . . ? C50 C49 C48 118.3(5) . . ? C54 C49 C48 123.9(5) . . ? C51 C50 C49 121.4(6) . . ? C51 C50 H50 119.3 . . ? C49 C50 H50 119.3 . . ? C50 C51 C52 119.8(5) . . ? C50 C51 H51 120.1 . . ? C52 C51 H51 120.1 . . ? C51 C52 C53 120.2(5) . . ? C51 C52 C55 119.8(5) . . ? C53 C52 C55 120.0(5) . . ? C54 C53 C52 119.8(6) . . ? C54 C53 H53 120.1 . . ? C52 C53 H53 120.1 . . ? C53 C54 C49 120.9(5) . . ? C53 C54 H54 119.6 . . ? C49 C54 H54 119.6 . . ? N3 C55 C52 178.2(7) . . ? 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 C68 Br4 C61 C62 156(6) . . . . ? C68 Br4 C61 C66 -25(6) . . . . ? C66 C61 C62 C63 1.8(9) . . . . ? C68 C61 C62 C63 -175.6(10) . . . . ? Br4 C61 C62 C63 -179.0(4) . . . . ? C61 C62 C63 C64 -2.6(9) . . . . ? C62 C63 C64 C65 1.7(8) . . . . ? C62 C63 C64 C67 -179.5(5) . . . . ? C63 C64 C65 C66 -0.1(8) . . . . ? C67 C64 C65 C66 -178.8(5) . . . . ? C64 C65 C66 C61 -0.7(9) . . . . ? C62 C61 C66 C65 -0.2(8) . . . . ? C68 C61 C66 C65 177.4(9) . . . . ? Br4 C61 C66 C65 -179.4(4) . . . . ? C63 C64 C67 C67 176.3(7) . . . 2_656 ? C65 C64 C67 C67 -5.0(11) . . . 2_656 ? C61 Br4 C68 N4 146(12) . . . . ? C62 C61 C68 Br4 -26(7) . . . . ? C66 C61 C68 Br4 157(6) . . . . ? C62 C61 C68 N4 -70(13) . . . . ? C66 C61 C68 N4 113(13) . . . . ? Br4 C61 C68 N4 -44(12) . . . . ? C6 C1 C2 C3 -0.6(10) . . . . ? Br1 C1 C2 C3 179.4(5) . . . . ? C1 C2 C3 C4 0.7(10) . . . . ? C2 C3 C4 C5 0.3(9) . . . . ? C2 C3 C4 C7 178.2(6) . . . . ? C3 C4 C5 C6 -1.4(9) . . . . ? C7 C4 C5 C6 -179.3(6) . . . . ? C4 C5 C6 C1 1.5(10) . . . . ? C2 C1 C6 C5 -0.5(10) . . . . ? Br1 C1 C6 C5 179.5(5) . . . . ? C3 C4 C7 C8 -175.6(7) . . . . ? C5 C4 C7 C8 2.2(11) . . . . ? C4 C7 C8 C9 -179.4(7) . . . . ? C7 C8 C9 C14 -180.0(7) . . . . ? C7 C8 C9 C10 -1.9(12) . . . . ? C14 C9 C10 C11 2.5(10) . . . . ? C8 C9 C10 C11 -175.5(6) . . . . ? C9 C10 C11 C12 -2.1(10) . . . . ? C10 C11 C12 C13 0.9(10) . . . . ? C10 C11 C12 C15 179.7(6) . . . . ? C11 C12 C13 C14 -0.3(10) . . . . ? C15 C12 C13 C14 -179.2(6) . . . . ? C12 C13 C14 C9 0.9(11) . . . . ? C10 C9 C14 C13 -2.0(11) . . . . ? C8 C9 C14 C13 176.1(7) . . . . ? C13 C12 C15 N1 -165(100) . . . . ? C11 C12 C15 N1 16(35) . . . . ? C26 C21 C22 C23 0.5(9) . . . . ? Br2 C21 C22 C23 -179.7(5) . . . . ? C21 C22 C23 C24 0.6(9) . . . . ? C22 C23 C24 C25 -1.0(9) . . . . ? C22 C23 C24 C27 179.6(6) . . . . ? C23 C24 C25 C26 0.3(10) . . . . ? C27 C24 C25 C26 179.7(6) . . . . ? C24 C25 C26 C21 0.8(10) . . . . ? C22 C21 C26 C25 -1.2(10) . . . . ? Br2 C21 C26 C25 179.0(5) . . . . ? C25 C24 C27 C28 6.1(10) . . . . ? C23 C24 C27 C28 -174.4(6) . . . . ? C24 C27 C28 C29 -179.8(5) . . . . ? C27 C28 C29 C34 172.4(6) . . . . ? C27 C28 C29 C30 -9.4(10) . . . . ? C34 C29 C30 C31 -1.6(9) . . . . ? C28 C29 C30 C31 -179.9(6) . . . . ? C29 C30 C31 C32 -0.1(9) . . . . ? C30 C31 C32 C33 0.7(9) . . . . ? C30 C31 C32 C35 -180.0(6) . . . . ? C31 C32 C33 C34 0.5(9) . . . . ? C35 C32 C33 C34 -178.9(6) . . . . ? C32 C33 C34 C29 -2.3(10) . . . . ? C30 C29 C34 C33 2.8(9) . . . . ? C28 C29 C34 C33 -178.8(6) . . . . ? C31 C32 C35 N2 -108(34) . . . . ? C33 C32 C35 N2 72(34) . . . . ? C46 C41 C42 C43 2.1(9) . . . . ? Br3 C41 C42 C43 -178.5(4) . . . . ? C41 C42 C43 C44 -0.2(9) . . . . ? C42 C43 C44 C45 -1.2(9) . . . . ? C42 C43 C44 C47 177.4(6) . . . . ? C43 C44 C45 C46 0.9(9) . . . . ? C47 C44 C45 C46 -177.8(6) . . . . ? C42 C41 C46 C45 -2.4(9) . . . . ? Br3 C41 C46 C45 178.2(5) . . . . ? C44 C45 C46 C41 0.9(10) . . . . ? C43 C44 C47 C48 1.4(10) . . . . ? C45 C44 C47 C48 -179.9(6) . . . . ? C44 C47 C48 C49 -179.2(6) . . . . ? C47 C48 C49 C50 -168.4(6) . . . . ? C47 C48 C49 C54 11.9(10) . . . . ? C54 C49 C50 C51 -1.1(9) . . . . ? C48 C49 C50 C51 179.1(6) . . . . ? C49 C50 C51 C52 1.0(9) . . . . ? C50 C51 C52 C53 -0.2(9) . . . . ? C50 C51 C52 C55 179.6(6) . . . . ? C51 C52 C53 C54 -0.4(9) . . . . ? C55 C52 C53 C54 179.8(6) . . . . ? C52 C53 C54 C49 0.3(9) . . . . ? C50 C49 C54 C53 0.4(9) . . . . ? C48 C49 C54 C53 -179.8(6) . . . . ? C51 C52 C55 N3 50(24) . . . . ? C53 C52 C55 N3 -131(24) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C46 H46 N3 0.9500 2.5200 3.421(9) 158.00 1_545 ? C62 H62 N3 0.9500 2.5900 3.340(8) 136.00 1_545 ? C66 H66 N1 0.9500 2.4700 3.235(10) 137.00 2_666 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.089 _refine_diff_density_min -1.159 _refine_diff_density_rms 0.107