data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H18 Br2 F N3 O' _chemical_formula_sum 'C21 H18 Br2 F N3 O' _chemical_formula_weight 507.20 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P21212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 19.716(5) _cell_length_b 23.201(6) _cell_length_c 4.2513(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1944.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used 17594 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.732 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 4.195 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.465 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku SCX-Mini with Mercury 2 CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17545 _diffrn_reflns_av_R_equivalents 0.0798 _diffrn_reflns_av_sigmaI/netI 0.0698 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4466 _reflns_number_gt 3864 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-ray Diffraction Data. Hooft, R. W. W., Straver, L. H. and Spek, A. L. (2008). J. Appl. Cryst., 41, 96-103. Determination of absolute structure using Bayesian statistics on Bijvoet differences. Sheldrick, G. M. (2008). SHELXL-97. Acta Cryst., A64, 112-122. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_acknowledgements ; The data were collected using instrumentation purchased with funds provided by the National Science Foundation Grant No. 0741973. ; _chemical_absolute_configuration ad # syn absolute configuration from synthetic procedure # ad absolute configuration from anomalous dispersion effects # rm absolute configuration from reference to a chiral # reference molecule of known abs. conf. # Hooft, R. W. W., Straver, L. H. and Spek, A. L. (2008). J. Appl. Cryst., # 41, 96-103. Determination of absolute structure using Bayesian # statistics on Bijvoet differences. _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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. The absolute structure was determined by the method of Flack (Flack, 1983). The Flack x parameter refined to 0.030(12). The assignment was corroborated by use of Hooft's y-parameter (Hooft, Straver and Spek, 2008), which refined to 0.033(9). ; _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^)+(0.0439P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.030(12) _refine_ls_number_reflns 4466 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 C1 C 0.46413(19) 0.14596(17) 0.4662(10) 0.0244(9) Uani 1 1 d . . . C2 C 0.4287(2) 0.09317(19) 0.4498(10) 0.0284(9) Uani 1 1 d . . . H2 H 0.4465 0.0613 0.3361 0.034 Uiso 1 1 calc R . . C3 C 0.3678(2) 0.08931(18) 0.6033(10) 0.0279(9) Uani 1 1 d . . . H3 H 0.3429 0.0543 0.5968 0.033 Uiso 1 1 calc R . . C4 C 0.34190(19) 0.13628(17) 0.7691(10) 0.0270(9) Uani 1 1 d . . . C5 C 0.37562(19) 0.18763(16) 0.7957(10) 0.0226(8) Uani 1 1 d . . . H5 H 0.3574 0.2187 0.9142 0.027 Uiso 1 1 calc R . . C6 C 0.43786(19) 0.19247(16) 0.6417(9) 0.0232(9) Uani 1 1 d . . . C8 C 0.48661(19) 0.23884(17) 0.6157(9) 0.0217(8) Uani 1 1 d . . . C9 C 0.4895(2) 0.29503(17) 0.7358(10) 0.0266(9) Uani 1 1 d . . . H9 H 0.4539 0.3098 0.8632 0.032 Uiso 1 1 calc R . . C10 C 0.5448(2) 0.32816(17) 0.6652(10) 0.0285(9) Uani 1 1 d . . . C11 C 0.5981(2) 0.30705(19) 0.4778(11) 0.0328(10) Uani 1 1 d . . . H11 H 0.6361 0.3311 0.4362 0.039 Uiso 1 1 calc R . . C12 C 0.5963(2) 0.25238(19) 0.3539(10) 0.0300(10) Uani 1 1 d . . . H12 H 0.6320 0.2384 0.2243 0.036 Uiso 1 1 calc R . . C13 C 0.54015(19) 0.21809(17) 0.4254(10) 0.0241(9) Uani 1 1 d . . . C14 C 0.5671(2) 0.12723(19) 0.1241(9) 0.0291(9) Uani 1 1 d . . . H14A H 0.5916 0.1533 -0.0211 0.035 Uiso 1 1 calc R . . H14B H 0.5376 0.1019 -0.0041 0.035 Uiso 1 1 calc R . . C15 C 0.6181(2) 0.09049(17) 0.2978(9) 0.0223(8) Uani 1 1 d . . . H15 H 0.6421 0.1148 0.4569 0.027 Uiso 1 1 calc R . . C16 C 0.66998(19) 0.06283(17) 0.0832(9) 0.0250(9) Uani 1 1 d . . . H16A H 0.6461 0.0390 -0.0750 0.030 Uiso 1 1 calc R . . H16B H 0.6949 0.0935 -0.0304 0.030 Uiso 1 1 calc R . . C17 C 0.7743(2) 0.05053(17) 0.3960(9) 0.0249(9) Uani 1 1 d . . . C18 C 0.8283(2) 0.01567(18) 0.4875(11) 0.0313(10) Uani 1 1 d . . . H18 H 0.8276 -0.0247 0.4491 0.038 Uiso 1 1 calc R . . C19 C 0.8826(2) 0.0411(2) 0.6346(12) 0.0396(12) Uani 1 1 d . . . H19 H 0.9202 0.0184 0.6990 0.048 Uiso 1 1 calc R . . C20 C 0.8822(2) 0.1005(2) 0.6892(12) 0.0409(11) Uani 1 1 d . . . H20 H 0.9194 0.1193 0.7870 0.049 Uiso 1 1 calc R . . C21 C 0.8253(2) 0.13070(18) 0.5949(11) 0.0305(10) Uani 1 1 d . . . C22 C 0.7644(2) 0.21941(18) 0.5694(13) 0.0395(12) Uani 1 1 d . . . H22A H 0.7570 0.2151 0.3427 0.059 Uiso 1 1 calc R . . H22B H 0.7699 0.2603 0.6204 0.059 Uiso 1 1 calc R . . H22C H 0.7253 0.2039 0.6837 0.059 Uiso 1 1 calc R . . Br1 Br 0.25482(2) 0.127270(18) 0.96122(11) 0.03219(13) Uani 1 1 d . . . Br2 Br 0.55229(3) 0.40469(2) 0.82398(13) 0.04194(15) Uani 1 1 d . . . N1 N 0.52474(16) 0.16165(14) 0.3327(8) 0.0254(7) Uani 1 1 d . . . N2 N 0.71825(18) 0.02702(15) 0.2508(9) 0.0271(8) Uani 1 1 d . . . H2N H 0.726(2) -0.0037(19) 0.164(11) 0.032 Uiso 1 1 d . . . N3 N 0.77250(17) 0.10764(14) 0.4497(8) 0.0259(8) Uani 1 1 d . . . O1 O 0.82451(16) 0.18853(12) 0.6595(9) 0.0396(8) Uani 1 1 d . . . F1 F 0.58171(11) 0.04656(10) 0.4550(6) 0.0296(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 C1 0.018(2) 0.027(2) 0.028(2) 0.0019(18) -0.0051(17) 0.0029(16) C2 0.030(2) 0.026(2) 0.030(2) -0.001(2) -0.0068(18) 0.0043(18) C3 0.026(2) 0.024(2) 0.033(2) 0.001(2) -0.0113(17) -0.0038(18) C4 0.0162(19) 0.032(2) 0.032(2) 0.0042(19) -0.0032(16) -0.0012(17) C5 0.018(2) 0.0219(19) 0.028(2) 0.0009(18) -0.0053(17) 0.0014(16) C6 0.021(2) 0.022(2) 0.027(2) 0.0044(18) -0.0035(17) 0.0024(17) C8 0.0164(19) 0.027(2) 0.021(2) 0.0011(17) -0.0013(15) 0.0034(16) C9 0.020(2) 0.027(2) 0.033(2) 0.0035(19) 0.0032(17) 0.0029(17) C10 0.033(2) 0.0209(19) 0.032(2) 0.0021(19) -0.001(2) -0.0038(18) C11 0.020(2) 0.038(2) 0.040(3) 0.010(2) 0.005(2) -0.0050(18) C12 0.019(2) 0.039(2) 0.032(2) 0.003(2) 0.0065(17) 0.0055(18) C13 0.020(2) 0.026(2) 0.026(2) 0.0035(18) -0.0026(17) 0.0020(16) C14 0.030(2) 0.034(2) 0.023(2) 0.0014(19) -0.0002(16) 0.009(2) C15 0.025(2) 0.0223(19) 0.0197(19) 0.0002(18) 0.0014(16) -0.0004(17) C16 0.021(2) 0.029(2) 0.025(2) -0.0052(18) -0.0037(17) 0.0002(17) C17 0.023(2) 0.030(2) 0.023(2) -0.0025(18) 0.0081(16) -0.0007(17) C18 0.026(2) 0.026(2) 0.042(3) -0.003(2) 0.004(2) 0.0052(17) C19 0.025(2) 0.041(3) 0.052(3) -0.002(3) -0.005(2) 0.010(2) C20 0.027(2) 0.044(3) 0.051(3) -0.009(3) -0.009(2) 0.000(2) C21 0.024(2) 0.027(2) 0.041(3) -0.004(2) -0.0002(18) -0.0013(18) C22 0.032(3) 0.025(2) 0.061(3) -0.001(2) -0.002(2) 0.0009(19) Br1 0.0198(2) 0.0330(2) 0.0438(3) 0.00748(19) -0.00267(18) -0.00467(17) Br2 0.0399(3) 0.0306(2) 0.0553(3) -0.0039(2) 0.0081(2) -0.0145(2) N1 0.0230(18) 0.0258(18) 0.0275(17) -0.0009(16) -0.0008(14) 0.0074(14) N2 0.0241(19) 0.0236(18) 0.034(2) -0.0045(16) 0.0006(15) 0.0037(15) N3 0.0231(17) 0.0272(18) 0.0275(17) -0.0017(15) 0.0050(14) 0.0002(14) O1 0.0301(18) 0.0269(16) 0.062(2) -0.0084(16) -0.0124(16) -0.0008(13) F1 0.0235(12) 0.0308(12) 0.0345(13) 0.0059(12) 0.0016(10) 0.0000(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 C1 N1 1.372(5) . ? C1 C6 1.410(5) . ? C1 C2 1.412(6) . ? C2 C3 1.370(6) . ? C2 H2 0.9500 . ? C3 C4 1.395(6) . ? C3 H3 0.9500 . ? C4 C5 1.369(5) . ? C4 Br1 1.913(4) . ? C5 C6 1.395(5) . ? C5 H5 0.9500 . ? C6 C8 1.447(5) . ? C8 C9 1.401(5) . ? C8 C13 1.414(5) . ? C9 C10 1.367(5) . ? C9 H9 0.9500 . ? C10 C11 1.407(6) . ? C10 Br2 1.905(4) . ? C11 C12 1.374(6) . ? C11 H11 0.9500 . ? C12 C13 1.397(5) . ? C12 H12 0.9500 . ? C13 N1 1.401(5) . ? C14 N1 1.456(5) . ? C14 C15 1.511(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 F1 1.414(4) . ? C15 C16 1.514(5) . ? C15 H15 1.0000 . ? C16 N2 1.450(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 N3 1.345(5) . ? C17 N2 1.378(5) . ? C17 C18 1.392(6) . ? C18 C19 1.373(6) . ? C18 H18 0.9500 . ? C19 C20 1.399(6) . ? C19 H19 0.9500 . ? C20 C21 1.381(6) . ? C20 H20 0.9500 . ? C21 N3 1.323(5) . ? C21 O1 1.370(5) . ? C22 O1 1.437(5) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N2 H2N 0.82(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C6 109.6(3) . . ? N1 C1 C2 129.9(4) . . ? C6 C1 C2 120.5(4) . . ? C3 C2 C1 117.8(4) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 120.7(4) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 122.9(4) . . ? C5 C4 Br1 119.7(3) . . ? C3 C4 Br1 117.3(3) . . ? C4 C5 C6 117.3(4) . . ? C4 C5 H5 121.4 . . ? C6 C5 H5 121.4 . . ? C5 C6 C1 120.6(4) . . ? C5 C6 C8 132.8(4) . . ? C1 C6 C8 106.5(3) . . ? C9 C8 C13 119.7(4) . . ? C9 C8 C6 133.7(4) . . ? C13 C8 C6 106.6(3) . . ? C10 C9 C8 118.4(4) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? C9 C10 C11 121.6(4) . . ? C9 C10 Br2 120.5(3) . . ? C11 C10 Br2 117.8(3) . . ? C12 C11 C10 121.3(4) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 117.6(4) . . ? C11 C12 H12 121.2 . . ? C13 C12 H12 121.2 . . ? C12 C13 N1 130.0(4) . . ? C12 C13 C8 121.5(4) . . ? N1 C13 C8 108.5(3) . . ? N1 C14 C15 113.2(3) . . ? N1 C14 H14A 108.9 . . ? C15 C14 H14A 108.9 . . ? N1 C14 H14B 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.8 . . ? F1 C15 C14 107.5(3) . . ? F1 C15 C16 108.8(3) . . ? C14 C15 C16 113.3(3) . . ? F1 C15 H15 109.1 . . ? C14 C15 H15 109.1 . . ? C16 C15 H15 109.1 . . ? N2 C16 C15 113.0(3) . . ? N2 C16 H16A 109.0 . . ? C15 C16 H16A 109.0 . . ? N2 C16 H16B 109.0 . . ? C15 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? N3 C17 N2 116.4(4) . . ? N3 C17 C18 123.0(4) . . ? N2 C17 C18 120.5(4) . . ? C19 C18 C17 118.3(4) . . ? C19 C18 H18 120.8 . . ? C17 C18 H18 120.8 . . ? C18 C19 C20 119.6(4) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C21 C20 C19 117.1(4) . . ? C21 C20 H20 121.4 . . ? C19 C20 H20 121.4 . . ? N3 C21 O1 118.7(4) . . ? N3 C21 C20 124.7(4) . . ? O1 C21 C20 116.6(4) . . ? O1 C22 H22A 109.5 . . ? O1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C1 N1 C13 108.7(3) . . ? C1 N1 C14 127.3(3) . . ? C13 N1 C14 124.0(3) . . ? C17 N2 C16 121.3(3) . . ? C17 N2 H2N 114(3) . . ? C16 N2 H2N 113(3) . . ? C21 N3 C17 117.2(4) . . ? C21 O1 C22 116.4(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 N1 C1 C2 C3 -179.0(4) . . . . ? C6 C1 C2 C3 1.4(6) . . . . ? C1 C2 C3 C4 0.2(6) . . . . ? C2 C3 C4 C5 -1.7(6) . . . . ? C2 C3 C4 Br1 177.6(3) . . . . ? C3 C4 C5 C6 1.5(6) . . . . ? Br1 C4 C5 C6 -177.8(3) . . . . ? C4 C5 C6 C1 0.1(6) . . . . ? C4 C5 C6 C8 179.7(4) . . . . ? N1 C1 C6 C5 178.7(3) . . . . ? C2 C1 C6 C5 -1.6(6) . . . . ? N1 C1 C6 C8 -1.0(4) . . . . ? C2 C1 C6 C8 178.7(4) . . . . ? C5 C6 C8 C9 0.6(8) . . . . ? C1 C6 C8 C9 -179.8(4) . . . . ? C5 C6 C8 C13 -179.6(4) . . . . ? C1 C6 C8 C13 0.0(4) . . . . ? C13 C8 C9 C10 -0.3(6) . . . . ? C6 C8 C9 C10 179.5(4) . . . . ? C8 C9 C10 C11 -0.2(6) . . . . ? C8 C9 C10 Br2 -179.4(3) . . . . ? C9 C10 C11 C12 1.0(7) . . . . ? Br2 C10 C11 C12 -179.8(3) . . . . ? C10 C11 C12 C13 -1.1(7) . . . . ? C11 C12 C13 N1 179.7(4) . . . . ? C11 C12 C13 C8 0.6(6) . . . . ? C9 C8 C13 C12 0.1(6) . . . . ? C6 C8 C13 C12 -179.7(4) . . . . ? C9 C8 C13 N1 -179.2(3) . . . . ? C6 C8 C13 N1 1.0(4) . . . . ? N1 C14 C15 F1 69.9(4) . . . . ? N1 C14 C15 C16 -169.9(3) . . . . ? F1 C15 C16 N2 -59.8(4) . . . . ? C14 C15 C16 N2 -179.2(3) . . . . ? N3 C17 C18 C19 -1.1(6) . . . . ? N2 C17 C18 C19 -179.2(4) . . . . ? C17 C18 C19 C20 0.2(7) . . . . ? C18 C19 C20 C21 1.2(7) . . . . ? C19 C20 C21 N3 -2.0(8) . . . . ? C19 C20 C21 O1 177.8(4) . . . . ? C6 C1 N1 C13 1.6(4) . . . . ? C2 C1 N1 C13 -178.0(4) . . . . ? C6 C1 N1 C14 -177.4(3) . . . . ? C2 C1 N1 C14 3.0(7) . . . . ? C12 C13 N1 C1 179.2(4) . . . . ? C8 C13 N1 C1 -1.6(4) . . . . ? C12 C13 N1 C14 -1.8(7) . . . . ? C8 C13 N1 C14 177.4(3) . . . . ? C15 C14 N1 C1 -89.2(5) . . . . ? C15 C14 N1 C13 91.9(5) . . . . ? N3 C17 N2 C16 17.7(5) . . . . ? C18 C17 N2 C16 -164.1(4) . . . . ? C15 C16 N2 C17 -82.8(4) . . . . ? O1 C21 N3 C17 -178.6(4) . . . . ? C20 C21 N3 C17 1.2(6) . . . . ? N2 C17 N3 C21 178.6(4) . . . . ? C18 C17 N3 C21 0.4(6) . . . . ? N3 C21 O1 C22 1.6(6) . . . . ? C20 C21 O1 C22 -178.2(4) . . . . ? 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 N2 H2N Br1 0.82(4) 3.02(5) 3.823(4) 169(4) 2_654 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.862 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.092