# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Oleg Shishkin' _publ_contact_author_email SHISHKIN@XRAY.ISC.KHARKOV.COM _publ_section_title ; Layered Crystal Structure of Bicyclic Aziridines as Revealed by Analysis of Intermolecular Interactions Energy ; loop_ _publ_author_name 'Oleg Shishkin' 'Valentin A. Chebanov' 'Sergey M Desenko' 'Viktoriya V. Dyakonenko' 'Andrey V. Maleev' ; A.I.Zbruyev ; # Attachment 'str1.cif' data_foto5 _database_code_depnum_ccdc_archive 'CCDC 737521' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 F N2' _chemical_formula_weight 280.34 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' _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 9.3776(11) _cell_length_b 9.5002(10) _cell_length_c 9.7109(12) _cell_angle_alpha 70.320(11) _cell_angle_beta 66.525(12) _cell_angle_gamma 89.942(9) _cell_volume 738.25(18) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.952 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details 'Blessing, R. H. Acta Crystallogr., Sect A 1995, 51, 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Xcalibur"3 _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 16.1827 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_decay_% ? _diffrn_reflns_number 6478 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3356 _reflns_number_gt 2772 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0567P)^2^+0.1885P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3356 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1175 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 F1 F 0.22898(11) 0.55957(10) -0.31376(10) 0.0395(2) Uani 1 1 d . . . N1 N 0.09426(12) 0.11455(12) 0.65801(12) 0.0216(2) Uani 1 1 d . . . N2 N 0.23803(12) 0.27877(11) 0.38031(12) 0.0206(2) Uani 1 1 d . . . C1 C 0.07769(14) 0.31425(13) 0.44869(14) 0.0207(2) Uani 1 1 d . . . H1 H 0.0575 0.4191 0.4194 0.025 Uiso 1 1 calc R . . C2 C 0.00389(14) 0.20675(13) 0.62028(14) 0.0201(2) Uani 1 1 d . . . C3 C 0.25049(14) 0.15748(14) 0.51934(14) 0.0212(3) Uani 1 1 d . . . C4 C 0.36293(15) 0.22893(16) 0.56428(16) 0.0277(3) Uani 1 1 d . . . H4A H 0.3293 0.3203 0.5793 0.041 Uiso 1 1 calc R . . H4B H 0.4673 0.2520 0.4793 0.041 Uiso 1 1 calc R . . H4C H 0.3629 0.1594 0.6625 0.041 Uiso 1 1 calc R . . C5 C 0.30660(15) 0.01998(15) 0.47864(16) 0.0273(3) Uani 1 1 d . . . H5A H 0.2340 -0.0211 0.4496 0.041 Uiso 1 1 calc R . . H5B H 0.3122 -0.0552 0.5708 0.041 Uiso 1 1 calc R . . H5C H 0.4089 0.0496 0.3898 0.041 Uiso 1 1 calc R . . C6 C -0.15722(14) 0.20449(13) 0.73647(15) 0.0210(2) Uani 1 1 d . . . C7 C -0.26088(15) 0.28647(15) 0.68356(17) 0.0274(3) Uani 1 1 d . . . H7 H -0.2291 0.3419 0.5742 0.033 Uiso 1 1 calc R . . C8 C -0.41215(16) 0.28555(17) 0.7941(2) 0.0340(3) Uani 1 1 d . . . H8 H -0.4811 0.3403 0.7586 0.041 Uiso 1 1 calc R . . C9 C -0.45947(16) 0.20319(17) 0.9566(2) 0.0357(3) Uani 1 1 d . . . H9 H -0.5603 0.2028 1.0303 0.043 Uiso 1 1 calc R . . C10 C -0.35734(16) 0.12141(16) 1.00977(17) 0.0331(3) Uani 1 1 d . . . H10 H -0.3899 0.0661 1.1192 0.040 Uiso 1 1 calc R . . C11 C -0.20654(15) 0.12124(14) 0.90101(16) 0.0257(3) Uani 1 1 d . . . H11 H -0.1384 0.0658 0.9376 0.031 Uiso 1 1 calc R . . C12 C 0.12182(13) 0.23711(13) 0.32844(14) 0.0192(2) Uani 1 1 d . . . H12 H 0.0801 0.1292 0.3715 0.023 Uiso 1 1 calc R . . C13 C 0.15197(13) 0.32254(13) 0.15736(14) 0.0197(2) Uani 1 1 d . . . C14 C 0.25540(16) 0.45893(14) 0.06798(15) 0.0260(3) Uani 1 1 d . . . H14 H 0.3069 0.4967 0.1156 0.031 Uiso 1 1 calc R . . C15 C 0.28236(17) 0.53879(15) -0.09085(16) 0.0291(3) Uani 1 1 d . . . H15 H 0.3518 0.6293 -0.1509 0.035 Uiso 1 1 calc R . . C16 C 0.20353(16) 0.48037(15) -0.15718(15) 0.0268(3) Uani 1 1 d . . . C17 C 0.10141(16) 0.34646(16) -0.07446(16) 0.0281(3) Uani 1 1 d . . . H17 H 0.0507 0.3099 -0.1235 0.034 Uiso 1 1 calc R . . C18 C 0.07571(14) 0.26675(15) 0.08486(15) 0.0241(3) Uani 1 1 d . . . H18 H 0.0071 0.1756 0.1433 0.029 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 F1 0.0506(5) 0.0439(5) 0.0206(4) -0.0055(4) -0.0169(4) 0.0039(4) N1 0.0203(5) 0.0232(5) 0.0198(5) -0.0079(4) -0.0071(4) 0.0037(4) N2 0.0206(5) 0.0225(5) 0.0198(5) -0.0090(4) -0.0087(4) 0.0024(4) C1 0.0221(6) 0.0202(5) 0.0202(6) -0.0084(5) -0.0085(5) 0.0046(4) C2 0.0215(6) 0.0217(6) 0.0195(6) -0.0105(5) -0.0086(5) 0.0028(4) C3 0.0194(6) 0.0248(6) 0.0183(5) -0.0070(5) -0.0074(4) 0.0039(4) C4 0.0239(6) 0.0351(7) 0.0261(6) -0.0116(5) -0.0124(5) 0.0035(5) C5 0.0258(6) 0.0300(7) 0.0278(6) -0.0126(5) -0.0113(5) 0.0104(5) C6 0.0198(5) 0.0223(6) 0.0239(6) -0.0135(5) -0.0082(5) 0.0021(4) C7 0.0274(6) 0.0324(7) 0.0330(7) -0.0203(6) -0.0164(5) 0.0085(5) C8 0.0235(6) 0.0390(8) 0.0546(9) -0.0307(7) -0.0201(6) 0.0113(6) C9 0.0207(6) 0.0337(7) 0.0474(9) -0.0247(7) -0.0011(6) 0.0001(5) C10 0.0306(7) 0.0277(7) 0.0293(7) -0.0125(6) 0.0005(6) -0.0014(5) C11 0.0246(6) 0.0233(6) 0.0258(6) -0.0106(5) -0.0060(5) 0.0015(5) C12 0.0192(5) 0.0197(5) 0.0191(5) -0.0081(4) -0.0077(4) 0.0033(4) C13 0.0203(5) 0.0218(6) 0.0191(6) -0.0102(5) -0.0081(4) 0.0062(4) C14 0.0312(6) 0.0244(6) 0.0240(6) -0.0095(5) -0.0126(5) 0.0004(5) C15 0.0363(7) 0.0239(6) 0.0231(6) -0.0070(5) -0.0099(5) 0.0002(5) C16 0.0315(7) 0.0311(7) 0.0168(6) -0.0076(5) -0.0102(5) 0.0083(5) C17 0.0280(6) 0.0367(7) 0.0249(6) -0.0146(6) -0.0136(5) 0.0037(5) C18 0.0231(6) 0.0268(6) 0.0231(6) -0.0105(5) -0.0095(5) 0.0023(5) _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 F1 C16 1.3696(14) . ? N1 C2 1.2843(16) . ? N1 C3 1.4784(15) . ? N2 C1 1.4730(15) . ? N2 C12 1.4732(15) . ? N2 C3 1.4973(16) . ? C1 C2 1.4950(17) . ? C1 C12 1.5042(16) . ? C2 C6 1.4770(16) . ? C3 C5 1.5232(17) . ? C3 C4 1.5266(18) . ? C6 C7 1.3937(18) . ? C6 C11 1.3976(18) . ? C7 C8 1.3948(19) . ? C8 C9 1.382(2) . ? C9 C10 1.382(2) . ? C10 C11 1.3879(18) . ? C12 C13 1.4890(16) . ? C13 C18 1.3933(17) . ? C13 C14 1.3954(17) . ? C14 C15 1.3856(18) . ? C15 C16 1.375(2) . ? C16 C17 1.372(2) . ? C17 C18 1.3926(18) . ? 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 108.32(10) . . ? C1 N2 C12 61.40(7) . . ? C1 N2 C3 104.38(9) . . ? C12 N2 C3 115.34(9) . . ? N2 C1 C2 105.38(10) . . ? N2 C1 C12 59.30(7) . . ? C2 C1 C12 113.50(10) . . ? N1 C2 C6 122.60(11) . . ? N1 C2 C1 113.39(10) . . ? C6 C2 C1 124.01(11) . . ? N1 C3 N2 108.03(9) . . ? N1 C3 C5 110.64(10) . . ? N2 C3 C5 112.05(10) . . ? N1 C3 C4 107.45(10) . . ? N2 C3 C4 106.67(10) . . ? C5 C3 C4 111.76(10) . . ? C7 C6 C11 119.36(11) . . ? C7 C6 C2 120.44(12) . . ? C11 C6 C2 120.20(11) . . ? C6 C7 C8 120.17(13) . . ? C9 C8 C7 119.96(14) . . ? C8 C9 C10 120.14(12) . . ? C9 C10 C11 120.49(14) . . ? C10 C11 C6 119.88(13) . . ? N2 C12 C13 115.80(10) . . ? N2 C12 C1 59.29(7) . . ? C13 C12 C1 120.83(10) . . ? C18 C13 C14 119.18(11) . . ? C18 C13 C12 119.92(11) . . ? C14 C13 C12 120.90(11) . . ? C15 C14 C13 120.79(12) . . ? C16 C15 C14 118.12(12) . . ? F1 C16 C17 118.51(12) . . ? F1 C16 C15 118.28(12) . . ? C17 C16 C15 123.21(12) . . ? C16 C17 C18 118.21(12) . . ? C17 C18 C13 120.49(12) . . ? 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 C12 N2 C1 C2 108.52(10) . . . . ? C3 N2 C1 C2 -2.79(12) . . . . ? C3 N2 C1 C12 -111.31(10) . . . . ? C3 N1 C2 C6 -174.63(10) . . . . ? C3 N1 C2 C1 5.70(14) . . . . ? N2 C1 C2 N1 -1.82(14) . . . . ? C12 C1 C2 N1 60.94(14) . . . . ? N2 C1 C2 C6 178.52(10) . . . . ? C12 C1 C2 C6 -118.73(12) . . . . ? C2 N1 C3 N2 -7.38(13) . . . . ? C2 N1 C3 C5 -130.37(11) . . . . ? C2 N1 C3 C4 107.37(12) . . . . ? C1 N2 C3 N1 5.99(12) . . . . ? C12 N2 C3 N1 -58.84(12) . . . . ? C1 N2 C3 C5 128.13(10) . . . . ? C12 N2 C3 C5 63.29(13) . . . . ? C1 N2 C3 C4 -109.26(10) . . . . ? C12 N2 C3 C4 -174.10(9) . . . . ? N1 C2 C6 C7 -168.03(12) . . . . ? C1 C2 C6 C7 11.60(18) . . . . ? N1 C2 C6 C11 12.66(18) . . . . ? C1 C2 C6 C11 -167.71(11) . . . . ? C11 C6 C7 C8 0.20(19) . . . . ? C2 C6 C7 C8 -179.12(11) . . . . ? C6 C7 C8 C9 0.0(2) . . . . ? C7 C8 C9 C10 -0.1(2) . . . . ? C8 C9 C10 C11 0.1(2) . . . . ? C9 C10 C11 C6 0.1(2) . . . . ? C7 C6 C11 C10 -0.25(18) . . . . ? C2 C6 C11 C10 179.07(11) . . . . ? C1 N2 C12 C13 112.02(11) . . . . ? C3 N2 C12 C13 -154.83(10) . . . . ? C3 N2 C12 C1 93.15(10) . . . . ? C2 C1 C12 N2 -94.48(11) . . . . ? N2 C1 C12 C13 -103.60(12) . . . . ? C2 C1 C12 C13 161.92(10) . . . . ? N2 C12 C13 C18 163.01(10) . . . . ? C1 C12 C13 C18 -128.83(12) . . . . ? N2 C12 C13 C14 -17.33(15) . . . . ? C1 C12 C13 C14 50.83(16) . . . . ? C18 C13 C14 C15 0.15(19) . . . . ? C12 C13 C14 C15 -179.51(11) . . . . ? C13 C14 C15 C16 0.5(2) . . . . ? C14 C15 C16 F1 179.52(11) . . . . ? C14 C15 C16 C17 -0.8(2) . . . . ? F1 C16 C17 C18 -179.81(11) . . . . ? C15 C16 C17 C18 0.5(2) . . . . ? C16 C17 C18 C13 0.12(19) . . . . ? C14 C13 C18 C17 -0.44(18) . . . . ? C12 C13 C18 C17 179.22(11) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.286 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.042 # Attachment 'str2.CIF' data_foto6 _database_code_depnum_ccdc_archive 'CCDC 737522' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 Cl I N2' _chemical_formula_sum 'C18 H16 Cl I N2' _chemical_formula_weight 422.68 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' Cl Cl 0.1484 0.1585 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4070(11) _cell_length_b 10.3158(11) _cell_length_c 10.7475(12) _cell_angle_alpha 116.008(11) _cell_angle_beta 97.704(9) _cell_angle_gamma 104.225(10) _cell_volume 872.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 1.985 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.499 _exptl_absorpt_correction_T_max 0.680 _exptl_absorpt_process_details 'Blessing, R. H. (1995) Acta Cryst. A51, 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 9019 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3953 _reflns_number_gt 3144 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0671P)^2^+0.0433P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3953 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1147 _refine_ls_wR_factor_gt 0.1055 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 0.14506(3) 0.84239(3) 0.50354(3) 0.07117(14) Uani 1 1 d . . . Cl1 Cl -0.52079(15) -0.44529(14) 0.30660(13) 0.0848(3) Uani 1 1 d . . . N1 N -0.1659(3) 0.0903(3) -0.1100(3) 0.0536(6) Uani 1 1 d . . . N2 N -0.3547(3) -0.1091(3) -0.1034(3) 0.0458(5) Uani 1 1 d . . . C1 C -0.3026(3) 0.0348(3) 0.0348(3) 0.0430(6) Uani 1 1 d . . . H1B H -0.3735 0.0656 0.0915 0.052 Uiso 1 1 calc R . . C2 C -0.1893(3) 0.1480(4) 0.0138(3) 0.0450(6) Uani 1 1 d . . . C3 C -0.2753(4) -0.0698(4) -0.1994(4) 0.0524(7) Uani 1 1 d . . . C4 C -0.3974(5) -0.0689(5) -0.3088(4) 0.0695(10) Uani 1 1 d . . . H4A H -0.4465 0.0015 -0.2585 0.104 Uiso 1 1 calc R . . H4B H -0.4718 -0.1701 -0.3667 0.104 Uiso 1 1 calc R . . H4C H -0.3502 -0.0377 -0.3697 0.104 Uiso 1 1 calc R . . C5 C -0.1939(5) -0.1788(5) -0.2735(5) 0.0717(11) Uani 1 1 d . . . H5A H -0.1187 -0.1770 -0.2023 0.108 Uiso 1 1 calc R . . H5B H -0.1448 -0.1477 -0.3335 0.108 Uiso 1 1 calc R . . H5C H -0.2665 -0.2810 -0.3317 0.108 Uiso 1 1 calc R . . C6 C -0.1115(3) 0.3095(4) 0.1274(3) 0.0446(6) Uani 1 1 d . . . C7 C -0.1531(4) 0.3673(4) 0.2545(4) 0.0510(7) Uani 1 1 d . . . H7A H -0.2310 0.3035 0.2679 0.061 Uiso 1 1 calc R . . C8 C -0.0806(4) 0.5187(4) 0.3621(4) 0.0539(7) Uani 1 1 d . . . H8A H -0.1094 0.5565 0.4471 0.065 Uiso 1 1 calc R . . C9 C 0.0350(3) 0.6125(4) 0.3412(4) 0.0515(7) Uani 1 1 d . . . C10 C 0.0770(4) 0.5582(4) 0.2170(5) 0.0678(10) Uani 1 1 d . . . H10A H 0.1545 0.6224 0.2036 0.081 Uiso 1 1 calc R . . C11 C 0.0033(4) 0.4057(4) 0.1098(4) 0.0638(9) Uani 1 1 d . . . H11A H 0.0324 0.3686 0.0250 0.077 Uiso 1 1 calc R . . C12 C -0.2543(3) -0.0986(4) 0.0198(3) 0.0455(6) Uani 1 1 d . . . H12A H -0.1484 -0.0882 0.0174 0.055 Uiso 1 1 calc R . . C13 C -0.3222(3) -0.1920(3) 0.0848(3) 0.0448(6) Uani 1 1 d . . . C14 C -0.4780(3) -0.2684(4) 0.0450(4) 0.0497(7) Uani 1 1 d . . . H14A H -0.5420 -0.2672 -0.0281 0.060 Uiso 1 1 calc R . . C15 C -0.5392(4) -0.3462(4) 0.1128(4) 0.0564(8) Uani 1 1 d . . . H15A H -0.6437 -0.3979 0.0853 0.068 Uiso 1 1 calc R . . C16 C -0.4440(4) -0.3466(4) 0.2216(4) 0.0553(8) Uani 1 1 d . . . C17 C -0.2903(4) -0.2733(4) 0.2619(4) 0.0617(9) Uani 1 1 d . . . H17A H -0.2277 -0.2734 0.3366 0.074 Uiso 1 1 calc R . . C18 C -0.2272(4) -0.1983(4) 0.1911(4) 0.0545(8) Uani 1 1 d . . . H18A H -0.1219 -0.1527 0.2149 0.065 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 0.0676(2) 0.05136(17) 0.0699(2) 0.02164(13) 0.01051(13) 0.00120(12) Cl1 0.1031(8) 0.0804(7) 0.0796(7) 0.0504(6) 0.0359(6) 0.0181(6) N1 0.0471(14) 0.0517(16) 0.0563(16) 0.0239(13) 0.0189(12) 0.0106(12) N2 0.0394(13) 0.0447(13) 0.0469(14) 0.0190(11) 0.0112(10) 0.0111(10) C1 0.0359(13) 0.0405(15) 0.0503(16) 0.0198(13) 0.0143(11) 0.0128(11) C2 0.0364(13) 0.0460(16) 0.0540(18) 0.0252(14) 0.0137(12) 0.0142(11) C3 0.0487(17) 0.0465(17) 0.0536(18) 0.0209(14) 0.0171(13) 0.0082(13) C4 0.066(2) 0.076(3) 0.055(2) 0.0306(19) 0.0124(17) 0.0109(19) C5 0.066(2) 0.068(2) 0.075(3) 0.026(2) 0.038(2) 0.0200(19) C6 0.0368(14) 0.0456(16) 0.0517(17) 0.0253(14) 0.0100(12) 0.0132(12) C7 0.0557(18) 0.0484(17) 0.0507(18) 0.0295(15) 0.0167(14) 0.0099(14) C8 0.0621(19) 0.0486(17) 0.0499(18) 0.0255(14) 0.0200(14) 0.0123(15) C9 0.0434(16) 0.0426(16) 0.0580(19) 0.0209(14) 0.0081(13) 0.0084(12) C10 0.056(2) 0.054(2) 0.078(3) 0.0231(18) 0.0304(18) 0.0041(16) C11 0.061(2) 0.054(2) 0.070(2) 0.0219(17) 0.0380(18) 0.0149(16) C12 0.0354(13) 0.0450(15) 0.0536(17) 0.0214(13) 0.0138(12) 0.0141(12) C13 0.0424(15) 0.0361(14) 0.0533(17) 0.0185(13) 0.0143(12) 0.0154(12) C14 0.0419(15) 0.0529(18) 0.0552(18) 0.0267(15) 0.0148(13) 0.0165(13) C15 0.0457(17) 0.0552(19) 0.063(2) 0.0272(16) 0.0185(14) 0.0112(14) C16 0.064(2) 0.0439(17) 0.056(2) 0.0227(15) 0.0251(16) 0.0158(15) C17 0.064(2) 0.057(2) 0.058(2) 0.0284(17) 0.0064(16) 0.0165(17) C18 0.0449(16) 0.0496(18) 0.060(2) 0.0235(15) 0.0067(14) 0.0122(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 I1 C9 2.102(3) . ? Cl1 C16 1.739(4) . ? N1 C2 1.273(4) . ? N1 C3 1.490(4) . ? N2 C12 1.465(4) . ? N2 C1 1.470(4) . ? N2 C3 1.487(4) . ? C1 C2 1.495(4) . ? C1 C12 1.503(4) . ? C1 H1B 0.9800 . ? C2 C6 1.476(4) . ? C3 C5 1.512(5) . ? C3 C4 1.534(5) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C11 1.371(5) . ? C6 C7 1.385(5) . ? C7 C8 1.386(5) . ? C7 H7A 0.9300 . ? C8 C9 1.383(5) . ? C8 H8A 0.9300 . ? C9 C10 1.359(5) . ? C10 C11 1.394(5) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 C13 1.494(4) . ? C12 H12A 0.9800 . ? C13 C14 1.386(4) . ? C13 C18 1.389(5) . ? C14 C15 1.381(5) . ? C14 H14A 0.9300 . ? C15 C16 1.376(5) . ? C15 H15A 0.9300 . ? C16 C17 1.363(5) . ? C17 C18 1.394(5) . ? C17 H17A 0.9300 . ? C18 H18A 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 C2 N1 C3 108.6(3) . . ? C12 N2 C1 61.59(19) . . ? C12 N2 C3 115.0(2) . . ? C1 N2 C3 104.8(2) . . ? N2 C1 C2 105.3(2) . . ? N2 C1 C12 59.02(19) . . ? C2 C1 C12 112.8(2) . . ? N2 C1 H1B 121.1 . . ? C2 C1 H1B 121.1 . . ? C12 C1 H1B 121.1 . . ? N1 C2 C6 124.1(3) . . ? N1 C2 C1 113.3(3) . . ? C6 C2 C1 122.7(3) . . ? N2 C3 N1 107.4(3) . . ? N2 C3 C5 113.2(3) . . ? N1 C3 C5 110.8(3) . . ? N2 C3 C4 106.4(3) . . ? N1 C3 C4 107.2(3) . . ? C5 C3 C4 111.5(3) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C11 C6 C7 118.5(3) . . ? C11 C6 C2 120.9(3) . . ? C7 C6 C2 120.6(3) . . ? C6 C7 C8 121.1(3) . . ? C6 C7 H7A 119.4 . . ? C8 C7 H7A 119.4 . . ? C9 C8 C7 119.0(3) . . ? C9 C8 H8A 120.5 . . ? C7 C8 H8A 120.5 . . ? C10 C9 C8 120.8(3) . . ? C10 C9 I1 120.0(2) . . ? C8 C9 I1 119.2(3) . . ? C9 C10 C11 119.6(3) . . ? C9 C10 H10A 120.2 . . ? C11 C10 H10A 120.2 . . ? C6 C11 C10 121.0(3) . . ? C6 C11 H11A 119.5 . . ? C10 C11 H11A 119.5 . . ? N2 C12 C13 117.4(2) . . ? N2 C12 C1 59.38(19) . . ? C13 C12 C1 119.7(2) . . ? N2 C12 H12A 116.1 . . ? C13 C12 H12A 116.1 . . ? C1 C12 H12A 116.1 . . ? C14 C13 C18 119.2(3) . . ? C14 C13 C12 121.7(3) . . ? C18 C13 C12 119.1(3) . . ? C15 C14 C13 120.6(3) . . ? C15 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? C16 C15 C14 119.4(3) . . ? C16 C15 H15A 120.3 . . ? C14 C15 H15A 120.3 . . ? C17 C16 C15 121.1(3) . . ? C17 C16 Cl1 119.5(3) . . ? C15 C16 Cl1 119.4(3) . . ? C16 C17 C18 119.9(3) . . ? C16 C17 H17A 120.0 . . ? C18 C17 H17A 120.0 . . ? C13 C18 C17 119.7(3) . . ? C13 C18 H18A 120.2 . . ? C17 C18 H18A 120.2 . . ? 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 C12 N2 C1 C2 107.8(2) . . . . ? C3 N2 C1 C2 -2.9(3) . . . . ? C3 N2 C1 C12 -110.7(3) . . . . ? C3 N1 C2 C6 -174.5(3) . . . . ? C3 N1 C2 C1 6.4(4) . . . . ? N2 C1 C2 N1 -2.2(3) . . . . ? C12 C1 C2 N1 60.1(3) . . . . ? N2 C1 C2 C6 178.6(2) . . . . ? C12 C1 C2 C6 -119.0(3) . . . . ? C12 N2 C3 N1 -58.8(3) . . . . ? C1 N2 C3 N1 6.4(3) . . . . ? C12 N2 C3 C5 63.9(4) . . . . ? C1 N2 C3 C5 129.1(3) . . . . ? C12 N2 C3 C4 -173.3(3) . . . . ? C1 N2 C3 C4 -108.1(3) . . . . ? C2 N1 C3 N2 -8.1(4) . . . . ? C2 N1 C3 C5 -132.3(3) . . . . ? C2 N1 C3 C4 105.9(3) . . . . ? N1 C2 C6 C11 -6.0(5) . . . . ? C1 C2 C6 C11 173.1(3) . . . . ? N1 C2 C6 C7 174.0(3) . . . . ? C1 C2 C6 C7 -6.9(4) . . . . ? C11 C6 C7 C8 -0.2(5) . . . . ? C2 C6 C7 C8 179.8(3) . . . . ? C6 C7 C8 C9 0.0(5) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C7 C8 C9 I1 179.8(2) . . . . ? C8 C9 C10 C11 -0.4(6) . . . . ? I1 C9 C10 C11 -179.9(3) . . . . ? C7 C6 C11 C10 0.1(6) . . . . ? C2 C6 C11 C10 -179.9(4) . . . . ? C9 C10 C11 C6 0.2(6) . . . . ? C1 N2 C12 C13 109.9(3) . . . . ? C3 N2 C12 C13 -156.1(3) . . . . ? C3 N2 C12 C1 94.0(3) . . . . ? C2 C1 C12 N2 -94.7(3) . . . . ? N2 C1 C12 C13 -106.2(3) . . . . ? C2 C1 C12 C13 159.1(3) . . . . ? N2 C12 C13 C14 -9.1(4) . . . . ? C1 C12 C13 C14 59.5(4) . . . . ? N2 C12 C13 C18 173.0(3) . . . . ? C1 C12 C13 C18 -118.4(3) . . . . ? C18 C13 C14 C15 1.9(5) . . . . ? C12 C13 C14 C15 -176.0(3) . . . . ? C13 C14 C15 C16 0.5(5) . . . . ? C14 C15 C16 C17 -1.0(5) . . . . ? C14 C15 C16 Cl1 -179.7(3) . . . . ? C15 C16 C17 C18 -0.9(6) . . . . ? Cl1 C16 C17 C18 177.8(3) . . . . ? C14 C13 C18 C17 -3.8(5) . . . . ? C12 C13 C18 C17 174.2(3) . . . . ? C16 C17 C18 C13 3.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.722 _refine_diff_density_min -0.913 _refine_diff_density_rms 0.069 # Attachment 'str3.cif' data_foto81 _database_code_depnum_ccdc_archive 'CCDC 737523' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 Br N2' _chemical_formula_sum 'C18 H17 Br N2' _chemical_formula_weight 341.25 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' 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 'P 2(1)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.199(2) _cell_length_b 16.027(2) _cell_length_c 10.752(3) _cell_angle_alpha 90.00 _cell_angle_beta 117.549(2) _cell_angle_gamma 90.00 _cell_volume 1558.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 2.633 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4010 _exptl_absorpt_correction_T_max 0.5970 _exptl_absorpt_process_details 'Blessing, R. H. (1995) Acta Cryst. A51, 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71069 _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 16884 _diffrn_reflns_av_R_equivalents 0.0799 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3526 _reflns_number_gt 3198 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1048P)^2^+2.8759P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3526 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1695 _refine_ls_wR_factor_gt 0.1567 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 Br1 Br 0.51867(6) -0.11639(3) 0.69549(6) 0.02417(18) Uani 1 1 d . . . N1 N 0.4469(5) 0.3131(3) 0.7509(4) 0.0187(8) Uani 1 1 d . . . N2 N 0.5492(5) 0.3737(3) 0.9824(4) 0.0182(8) Uani 1 1 d . . . C1 C 0.5719(6) 0.2823(3) 0.9898(5) 0.0195(10) Uani 1 1 d . . . H1B H 0.6624 0.2568 1.0621 0.023 Uiso 1 1 calc R . . C2 C 0.5048(5) 0.2541(3) 0.8405(5) 0.0174(9) Uani 1 1 d . . . C3 C 0.4784(6) 0.3929(3) 0.8289(5) 0.0195(10) Uani 1 1 d . . . C4 C 0.3389(6) 0.4445(3) 0.7839(5) 0.0213(10) Uani 1 1 d . . . H4A H 0.2685 0.4137 0.8016 0.032 Uiso 1 1 calc R . . H4B H 0.2974 0.4567 0.6856 0.032 Uiso 1 1 calc R . . H4C H 0.3626 0.4957 0.8362 0.032 Uiso 1 1 calc R . . C5 C 0.5924(6) 0.4408(4) 0.8016(6) 0.0237(10) Uani 1 1 d . . . H5A H 0.6799 0.4074 0.8305 0.036 Uiso 1 1 calc R . . H5B H 0.6171 0.4920 0.8538 0.036 Uiso 1 1 calc R . . H5C H 0.5517 0.4529 0.7033 0.036 Uiso 1 1 calc R . . C6 C 0.5041(5) 0.1656(3) 0.8032(5) 0.0186(10) Uani 1 1 d . . . C7 C 0.5611(7) 0.1056(3) 0.9087(5) 0.0236(11) Uani 1 1 d . . . H7A H 0.5958 0.1218 1.0017 0.028 Uiso 1 1 calc R . . C8 C 0.5671(7) 0.0215(3) 0.8771(5) 0.0267(12) Uani 1 1 d . . . H8A H 0.6069 -0.0182 0.9481 0.032 Uiso 1 1 calc R . . C9 C 0.5122(6) -0.0015(3) 0.7376(5) 0.0186(10) Uani 1 1 d . . . C10 C 0.4554(6) 0.0562(3) 0.6306(5) 0.0219(11) Uani 1 1 d . . . H10A H 0.4193 0.0394 0.5377 0.026 Uiso 1 1 calc R . . C11 C 0.4528(6) 0.1400(3) 0.6634(5) 0.0208(10) Uani 1 1 d . . . H11A H 0.4167 0.1796 0.5920 0.025 Uiso 1 1 calc R . . C12 C 0.4583(6) 0.3201(3) 1.0249(5) 0.0180(10) Uani 1 1 d . . . H12A H 0.3550 0.3127 0.9543 0.022 Uiso 1 1 calc R . . C13 C 0.4847(6) 0.3276(3) 1.1732(5) 0.0202(11) Uani 1 1 d . . . C14 C 0.6277(6) 0.3358(3) 1.2841(5) 0.0208(10) Uani 1 1 d . . . H14A H 0.7080 0.3394 1.2655 0.025 Uiso 1 1 calc R . . C15 C 0.6504(7) 0.3385(3) 1.4216(5) 0.0263(12) Uani 1 1 d . . . H15A H 0.7458 0.3446 1.4946 0.032 Uiso 1 1 calc R . . C16 C 0.5317(8) 0.3321(3) 1.4513(6) 0.0303(13) Uani 1 1 d . . . H16A H 0.5476 0.3327 1.5437 0.036 Uiso 1 1 calc R . . C17 C 0.3901(8) 0.3248(4) 1.3424(6) 0.0311(13) Uani 1 1 d . . . H17A H 0.3102 0.3218 1.3617 0.037 Uiso 1 1 calc R . . C18 C 0.3657(7) 0.3220(3) 1.2032(6) 0.0251(11) Uani 1 1 d . . . H18A H 0.2701 0.3165 1.1306 0.030 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 Br1 0.0330(3) 0.0142(2) 0.0230(3) -0.00240(19) 0.0110(2) 0.0005(2) N1 0.023(2) 0.016(2) 0.0154(18) -0.0021(15) 0.0077(16) 0.0015(17) N2 0.022(2) 0.0167(19) 0.0134(18) 0.0006(15) 0.0059(15) 0.0002(16) C1 0.025(2) 0.017(2) 0.013(2) -0.0004(17) 0.0064(19) 0.0003(19) C2 0.018(2) 0.020(2) 0.015(2) -0.0021(17) 0.0077(18) -0.0006(19) C3 0.024(2) 0.016(2) 0.013(2) -0.0024(17) 0.0044(19) -0.0011(19) C4 0.029(3) 0.015(2) 0.017(2) 0.0006(17) 0.009(2) 0.0039(19) C5 0.029(3) 0.020(2) 0.019(2) 0.0004(19) 0.009(2) -0.003(2) C6 0.022(2) 0.017(2) 0.016(2) -0.0015(19) 0.0091(19) -0.0012(18) C7 0.036(3) 0.019(2) 0.012(2) -0.0014(18) 0.008(2) 0.000(2) C8 0.044(3) 0.013(2) 0.018(2) 0.0025(19) 0.011(2) 0.001(2) C9 0.025(2) 0.012(2) 0.020(2) -0.0020(18) 0.0119(19) -0.0002(19) C10 0.026(3) 0.021(3) 0.014(2) 0.0004(19) 0.0057(19) 0.003(2) C11 0.020(2) 0.022(2) 0.017(2) 0.0017(19) 0.0057(18) 0.004(2) C12 0.019(2) 0.017(2) 0.014(2) -0.0011(17) 0.0049(18) -0.0013(18) C13 0.034(3) 0.010(2) 0.016(2) 0.0006(17) 0.012(2) 0.0019(19) C14 0.025(3) 0.018(2) 0.017(2) -0.0012(17) 0.008(2) -0.0015(19) C15 0.036(3) 0.020(2) 0.014(2) -0.0015(19) 0.004(2) -0.001(2) C16 0.054(4) 0.021(3) 0.019(2) -0.002(2) 0.019(3) -0.002(2) C17 0.047(4) 0.027(3) 0.028(3) 0.001(2) 0.025(3) 0.003(3) C18 0.034(3) 0.019(2) 0.020(2) 0.000(2) 0.010(2) 0.001(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 Br1 C9 1.905(5) . ? N1 C2 1.283(7) . ? N1 C3 1.481(6) . ? N2 C1 1.479(6) . ? N2 C12 1.482(6) . ? N2 C3 1.496(6) . ? C1 C2 1.494(6) . ? C1 C12 1.502(7) . ? C1 H1B 0.9800 . ? C2 C6 1.473(7) . ? C3 C4 1.519(7) . ? C3 C5 1.530(8) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.392(7) . ? C6 C11 1.404(7) . ? C7 C8 1.399(7) . ? C7 H7A 0.9300 . ? C8 C9 1.387(7) . ? C8 H8A 0.9300 . ? C9 C10 1.377(7) . ? C10 C11 1.393(7) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 C13 1.494(7) . ? C12 H12A 0.9800 . ? C13 C18 1.395(9) . ? C13 C14 1.399(7) . ? C14 C15 1.387(7) . ? C14 H14A 0.9300 . ? C15 C16 1.392(9) . ? C15 H15A 0.9300 . ? C16 C17 1.380(9) . ? C16 H16A 0.9300 . ? C17 C18 1.400(8) . ? C17 H17A 0.9300 . ? C18 H18A 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 C2 N1 C3 107.9(4) . . ? C1 N2 C12 61.0(3) . . ? C1 N2 C3 104.3(4) . . ? C12 N2 C3 114.0(4) . . ? N2 C1 C2 105.1(4) . . ? N2 C1 C12 59.6(3) . . ? C2 C1 C12 111.6(4) . . ? N2 C1 H1B 121.5 . . ? C2 C1 H1B 121.5 . . ? C12 C1 H1B 121.5 . . ? N1 C2 C6 124.3(4) . . ? N1 C2 C1 114.0(4) . . ? C6 C2 C1 121.7(4) . . ? N1 C3 N2 108.3(4) . . ? N1 C3 C4 111.3(4) . . ? N2 C3 C4 111.5(4) . . ? N1 C3 C5 108.0(4) . . ? N2 C3 C5 107.1(4) . . ? C4 C3 C5 110.4(4) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C11 118.7(4) . . ? C7 C6 C2 119.6(4) . . ? C11 C6 C2 121.6(4) . . ? C6 C7 C8 121.0(5) . . ? C6 C7 H7A 119.5 . . ? C8 C7 H7A 119.5 . . ? C9 C8 C7 118.5(5) . . ? C9 C8 H8A 120.7 . . ? C7 C8 H8A 120.7 . . ? C10 C9 C8 122.0(5) . . ? C10 C9 Br1 119.9(4) . . ? C8 C9 Br1 118.2(4) . . ? C9 C10 C11 119.1(5) . . ? C9 C10 H10A 120.5 . . ? C11 C10 H10A 120.5 . . ? C10 C11 C6 120.7(5) . . ? C10 C11 H11A 119.6 . . ? C6 C11 H11A 119.6 . . ? N2 C12 C13 116.9(4) . . ? N2 C12 C1 59.4(3) . . ? C13 C12 C1 121.4(4) . . ? N2 C12 H12A 115.7 . . ? C13 C12 H12A 115.7 . . ? C1 C12 H12A 115.7 . . ? C18 C13 C14 118.9(5) . . ? C18 C13 C12 119.7(5) . . ? C14 C13 C12 121.3(5) . . ? C15 C14 C13 120.4(5) . . ? C15 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? C14 C15 C16 120.5(5) . . ? C14 C15 H15A 119.7 . . ? C16 C15 H15A 119.7 . . ? C17 C16 C15 119.5(5) . . ? C17 C16 H16A 120.3 . . ? C15 C16 H16A 120.3 . . ? C16 C17 C18 120.5(6) . . ? C16 C17 H17A 119.7 . . ? C18 C17 H17A 119.7 . . ? C13 C18 C17 120.1(6) . . ? C13 C18 H18A 119.9 . . ? C17 C18 H18A 119.9 . . ? 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 C12 N2 C1 C2 106.6(4) . . . . ? C3 N2 C1 C2 -3.3(5) . . . . ? C3 N2 C1 C12 -109.9(4) . . . . ? C3 N1 C2 C6 -176.6(5) . . . . ? C3 N1 C2 C1 4.8(6) . . . . ? N2 C1 C2 N1 -0.9(6) . . . . ? C12 C1 C2 N1 61.9(6) . . . . ? N2 C1 C2 C6 -179.6(4) . . . . ? C12 C1 C2 C6 -116.8(5) . . . . ? C2 N1 C3 N2 -6.8(6) . . . . ? C2 N1 C3 C4 -129.8(5) . . . . ? C2 N1 C3 C5 108.8(5) . . . . ? C1 N2 C3 N1 6.0(5) . . . . ? C12 N2 C3 N1 -58.2(5) . . . . ? C1 N2 C3 C4 128.9(4) . . . . ? C12 N2 C3 C4 64.6(5) . . . . ? C1 N2 C3 C5 -110.2(5) . . . . ? C12 N2 C3 C5 -174.5(4) . . . . ? N1 C2 C6 C7 -175.6(5) . . . . ? C1 C2 C6 C7 3.0(8) . . . . ? N1 C2 C6 C11 7.1(8) . . . . ? C1 C2 C6 C11 -174.3(5) . . . . ? C11 C6 C7 C8 -0.2(9) . . . . ? C2 C6 C7 C8 -177.6(6) . . . . ? C6 C7 C8 C9 -1.2(9) . . . . ? C7 C8 C9 C10 1.4(9) . . . . ? C7 C8 C9 Br1 -179.3(5) . . . . ? C8 C9 C10 C11 0.0(8) . . . . ? Br1 C9 C10 C11 -179.4(4) . . . . ? C9 C10 C11 C6 -1.5(8) . . . . ? C7 C6 C11 C10 1.6(8) . . . . ? C2 C6 C11 C10 178.9(5) . . . . ? C1 N2 C12 C13 112.3(5) . . . . ? C3 N2 C12 C13 -154.2(4) . . . . ? C3 N2 C12 C1 93.5(4) . . . . ? C2 C1 C12 N2 -95.2(4) . . . . ? N2 C1 C12 C13 -104.8(5) . . . . ? C2 C1 C12 C13 160.0(4) . . . . ? N2 C12 C13 C18 143.1(5) . . . . ? C1 C12 C13 C18 -148.0(5) . . . . ? N2 C12 C13 C14 -40.3(7) . . . . ? C1 C12 C13 C14 28.7(7) . . . . ? C18 C13 C14 C15 -0.1(8) . . . . ? C12 C13 C14 C15 -176.8(5) . . . . ? C13 C14 C15 C16 0.8(8) . . . . ? C14 C15 C16 C17 -1.4(9) . . . . ? C15 C16 C17 C18 1.4(9) . . . . ? C14 C13 C18 C17 0.1(8) . . . . ? C12 C13 C18 C17 176.8(5) . . . . ? C16 C17 C18 C13 -0.8(9) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 1.040 _refine_diff_density_min -1.443 _refine_diff_density_rms 0.131