data_YL-I-122B _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H23 Br N2 O2' _chemical_formula_weight 427.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.1786(2) _cell_length_b 10.4497(2) _cell_length_c 19.1308(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2034.82(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 31708 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 28.4 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 2.039 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5991 _exptl_absorpt_correction_T_max 0.6404 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 77714 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0138 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.73 _reflns_number_total 5269 _reflns_number_gt 4998 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2009.3.0 (Bruker-AXS, 2009)' _computing_cell_refinement 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_data_reduction 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0362P)^2^+0.3490P] 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 0.001(4) _chemical_absolute_configuration ad _refine_ls_number_reflns 5269 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0245 _refine_ls_R_factor_gt 0.0222 _refine_ls_wR_factor_ref 0.0579 _refine_ls_wR_factor_gt 0.0569 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.310706(17) 0.231472(17) 0.145914(8) 0.03543(5) Uani 1 1 d . . . O1 O 0.28756(10) 0.77718(10) -0.09765(6) 0.0268(2) Uani 1 1 d . . . O2 O 0.07056(11) 0.82561(10) -0.10942(6) 0.0248(2) Uani 1 1 d . . . N1 N 0.14728(11) 0.62440(11) -0.12917(6) 0.0202(2) Uani 1 1 d . . . N2 N 0.13590(13) 0.36150(13) -0.28810(7) 0.0242(2) Uani 1 1 d . . . H2 H 0.077(2) 0.348(2) -0.3197(11) 0.038(5) Uiso 1 1 d . . . C1 C 0.01627(12) 0.57551(12) -0.14611(9) 0.0213(2) Uani 1 1 d . . . H1B H -0.0501 0.6428 -0.1371 0.026 Uiso 1 1 calc R . . H1A H -0.0042 0.5013 -0.1159 0.026 Uiso 1 1 calc R . . C2 C 0.01005(13) 0.53497(14) -0.22295(8) 0.0230(3) Uani 1 1 d . . . H2A H -0.0724 0.4877 -0.2324 0.028 Uiso 1 1 calc R . . H2B H 0.0133 0.6110 -0.2538 0.028 Uiso 1 1 calc R . . C3 C 0.12615(13) 0.45106(13) -0.23565(8) 0.0206(3) Uani 1 1 d . . . C4 C 0.25321(14) 0.29626(15) -0.28026(8) 0.0238(3) Uani 1 1 d . . . C5 C 0.30471(16) 0.19329(16) -0.31797(9) 0.0313(3) Uani 1 1 d . . . H5 H 0.2591 0.1588 -0.3570 0.038 Uiso 1 1 calc R . . C6 C 0.42347(16) 0.14323(16) -0.29691(10) 0.0347(4) Uani 1 1 d . . . H6 H 0.4593 0.0722 -0.3213 0.042 Uiso 1 1 calc R . . C7 C 0.49228(15) 0.19468(16) -0.24047(10) 0.0313(4) Uani 1 1 d . . . H7 H 0.5749 0.1594 -0.2278 0.038 Uiso 1 1 calc R . . C8 C 0.44184(13) 0.29661(14) -0.20265(8) 0.0250(3) Uani 1 1 d . . . H8 H 0.4892 0.3312 -0.1643 0.030 Uiso 1 1 calc R . . C9 C 0.31973(14) 0.34794(13) -0.22194(7) 0.0207(3) Uani 1 1 d . . . C10 C 0.23594(13) 0.44755(13) -0.19485(8) 0.0194(3) Uani 1 1 d . . . C11 C 0.25762(12) 0.53185(13) -0.13226(8) 0.0198(3) Uani 1 1 d . . . H11 H 0.3410 0.5808 -0.1395 0.024 Uiso 1 1 calc R . . C12 C 0.26878(13) 0.45792(14) -0.06399(8) 0.0201(3) Uani 1 1 d . . . C13 C 0.19316(14) 0.34906(13) -0.05110(7) 0.0226(3) Uani 1 1 d . . . H13 H 0.1343 0.3194 -0.0860 0.027 Uiso 1 1 calc R . . C14 C 0.20226(14) 0.28326(14) 0.01178(8) 0.0249(3) Uani 1 1 d . . . H14 H 0.1487 0.2106 0.0206 0.030 Uiso 1 1 calc R . . C15 C 0.29177(15) 0.32637(15) 0.06157(8) 0.0264(3) Uani 1 1 d . . . C16 C 0.36814(16) 0.43308(16) 0.05051(9) 0.0307(3) Uani 1 1 d . . . H16 H 0.4284 0.4612 0.0852 0.037 Uiso 1 1 calc R . . C17 C 0.35573(15) 0.49920(15) -0.01229(9) 0.0274(3) Uani 1 1 d . . . H17 H 0.4073 0.5736 -0.0201 0.033 Uiso 1 1 calc R . . C18 C 0.16196(12) 0.74942(12) -0.11205(7) 0.0191(2) Uani 1 1 d . . . C19 C 0.32628(16) 0.90713(14) -0.07509(9) 0.0292(3) Uani 1 1 d . . . C20 C 0.47437(18) 0.8945(2) -0.06767(15) 0.0573(7) Uani 1 1 d . . . H20A H 0.4947 0.8262 -0.0343 0.086 Uiso 1 1 calc R . . H20C H 0.5110 0.9755 -0.0507 0.086 Uiso 1 1 calc R . . H20B H 0.5129 0.8736 -0.1132 0.086 Uiso 1 1 calc R . . C21 C 0.2642(2) 0.9332(2) -0.00493(10) 0.0438(5) Uani 1 1 d . . . H21B H 0.1695 0.9466 -0.0110 0.066 Uiso 1 1 calc R . . H21C H 0.3036 1.0100 0.0156 0.066 Uiso 1 1 calc R . . H21A H 0.2789 0.8600 0.0261 0.066 Uiso 1 1 calc R . . C22 C 0.2874(3) 1.0070(2) -0.12908(12) 0.0591(7) Uani 1 1 d . . . H22B H 0.3175 0.9798 -0.1754 0.089 Uiso 1 1 calc R . . H22C H 0.3281 1.0892 -0.1171 0.089 Uiso 1 1 calc R . . H22A H 0.1917 1.0165 -0.1295 0.089 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 0.04282(9) 0.03801(9) 0.02546(7) -0.00262(6) -0.00692(6) 0.01403(7) O1 0.0229(5) 0.0179(5) 0.0397(6) -0.0104(5) 0.0018(4) -0.0035(4) O2 0.0294(5) 0.0173(5) 0.0276(5) -0.0024(4) -0.0041(4) 0.0043(4) N1 0.0153(5) 0.0144(5) 0.0310(7) -0.0034(4) 0.0011(4) -0.0003(4) N2 0.0232(6) 0.0267(6) 0.0226(6) -0.0046(5) 0.0008(5) -0.0034(5) C1 0.0159(5) 0.0175(6) 0.0306(7) 0.0000(6) 0.0015(5) -0.0009(4) C2 0.0196(6) 0.0209(6) 0.0285(7) 0.0024(6) -0.0016(5) -0.0008(5) C3 0.0205(6) 0.0171(6) 0.0241(7) 0.0009(5) 0.0026(5) -0.0032(5) C4 0.0205(6) 0.0254(8) 0.0255(7) -0.0050(6) 0.0052(5) -0.0061(5) C5 0.0251(7) 0.0343(8) 0.0345(8) -0.0154(6) 0.0097(6) -0.0088(6) C6 0.0234(7) 0.0279(8) 0.0528(11) -0.0185(7) 0.0161(7) -0.0055(6) C7 0.0183(6) 0.0248(8) 0.0509(10) -0.0087(7) 0.0087(6) -0.0010(5) C8 0.0191(6) 0.0215(7) 0.0343(8) -0.0056(6) 0.0051(5) -0.0031(5) C9 0.0188(6) 0.0169(6) 0.0263(6) -0.0036(5) 0.0059(5) -0.0046(5) C10 0.0177(6) 0.0161(6) 0.0243(7) -0.0025(5) 0.0041(5) -0.0011(5) C11 0.0130(5) 0.0156(6) 0.0308(8) -0.0062(5) 0.0028(5) -0.0004(4) C12 0.0151(5) 0.0181(6) 0.0270(7) -0.0065(5) -0.0003(5) 0.0020(5) C13 0.0208(6) 0.0202(6) 0.0267(7) -0.0044(5) -0.0042(6) -0.0002(5) C14 0.0245(6) 0.0223(7) 0.0279(7) -0.0043(5) -0.0027(5) 0.0023(6) C15 0.0280(7) 0.0270(7) 0.0242(7) -0.0062(6) -0.0045(6) 0.0104(6) C16 0.0290(7) 0.0306(8) 0.0325(8) -0.0112(7) -0.0105(6) 0.0038(6) C17 0.0225(6) 0.0244(7) 0.0354(8) -0.0088(6) -0.0066(6) -0.0019(5) C18 0.0229(6) 0.0163(6) 0.0179(6) -0.0020(5) 0.0025(4) -0.0018(5) C19 0.0341(8) 0.0171(6) 0.0364(8) -0.0086(6) -0.0016(6) -0.0075(6) C20 0.0307(9) 0.0414(11) 0.0998(19) -0.0379(12) 0.0046(10) -0.0137(8) C21 0.0475(10) 0.0462(11) 0.0379(10) -0.0199(8) -0.0067(8) 0.0008(8) C22 0.0879(17) 0.0360(10) 0.0533(13) 0.0140(9) -0.0080(11) -0.0293(11) _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 C15 1.9037(16) . ? O1 C18 1.3396(15) . ? O1 C19 1.4784(17) . ? O2 C18 1.2256(16) . ? N1 C18 1.3551(16) . ? N1 C1 1.4643(16) . ? N1 C11 1.4832(16) . ? N2 C3 1.3757(19) . ? N2 C4 1.3832(19) . ? N2 H2 0.86(2) . ? C1 C2 1.531(2) . ? C1 H1B 0.9900 . ? C1 H1A 0.9900 . ? C2 C3 1.4914(19) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C10 1.3637(19) . ? C4 C5 1.397(2) . ? C4 C9 1.412(2) . ? C5 C6 1.377(2) . ? C5 H5 0.9500 . ? C6 C7 1.395(3) . ? C6 H6 0.9500 . ? C7 C8 1.386(2) . ? C7 H7 0.9500 . ? C8 C9 1.403(2) . ? C8 H8 0.9500 . ? C9 C10 1.4420(18) . ? C10 C11 1.5027(19) . ? C11 C12 1.522(2) . ? C11 H11 1.0000 . ? C12 C13 1.3955(19) . ? C12 C17 1.396(2) . ? C13 C14 1.389(2) . ? C13 H13 0.9500 . ? C14 C15 1.393(2) . ? C14 H14 0.9500 . ? C15 C16 1.376(2) . ? C16 C17 1.392(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C19 C21 1.508(2) . ? C19 C20 1.520(2) . ? C19 C22 1.521(3) . ? C20 H20A 0.9800 . ? C20 H20C 0.9800 . ? C20 H20B 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C21 H21A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C22 H22A 0.9800 . ? 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 C18 O1 C19 120.89(11) . . ? C18 N1 C1 119.35(11) . . ? C18 N1 C11 123.69(11) . . ? C1 N1 C11 116.95(10) . . ? C3 N2 C4 108.57(12) . . ? C3 N2 H2 125.0(15) . . ? C4 N2 H2 126.4(15) . . ? N1 C1 C2 110.28(11) . . ? N1 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? N1 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? H1B C1 H1A 108.1 . . ? C3 C2 C1 106.64(12) . . ? C3 C2 H2A 110.4 . . ? C1 C2 H2A 110.4 . . ? C3 C2 H2B 110.4 . . ? C1 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? C10 C3 N2 109.89(13) . . ? C10 C3 C2 124.88(13) . . ? N2 C3 C2 125.17(13) . . ? N2 C4 C5 130.34(14) . . ? N2 C4 C9 108.12(12) . . ? C5 C4 C9 121.49(14) . . ? C6 C5 C4 118.07(14) . . ? C6 C5 H5 121.0 . . ? C4 C5 H5 121.0 . . ? C5 C6 C7 121.38(14) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C6 120.95(15) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 118.98(14) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C8 C9 C4 119.09(13) . . ? C8 C9 C10 134.85(13) . . ? C4 C9 C10 106.05(12) . . ? C3 C10 C9 107.36(12) . . ? C3 C10 C11 124.10(12) . . ? C9 C10 C11 128.51(12) . . ? N1 C11 C10 107.63(11) . . ? N1 C11 C12 110.69(11) . . ? C10 C11 C12 113.40(11) . . ? N1 C11 H11 108.3 . . ? C10 C11 H11 108.3 . . ? C12 C11 H11 108.3 . . ? C13 C12 C17 118.46(14) . . ? C13 C12 C11 121.62(12) . . ? C17 C12 C11 119.92(13) . . ? C14 C13 C12 121.32(13) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C15 118.42(14) . . ? C13 C14 H14 120.8 . . ? C15 C14 H14 120.8 . . ? C16 C15 C14 121.77(15) . . ? C16 C15 Br1 119.69(11) . . ? C14 C15 Br1 118.52(12) . . ? C15 C16 C17 118.94(14) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C16 C17 C12 121.06(15) . . ? C16 C17 H17 119.5 . . ? C12 C17 H17 119.5 . . ? O2 C18 O1 125.12(12) . . ? O2 C18 N1 123.54(12) . . ? O1 C18 N1 111.33(11) . . ? O1 C19 C21 108.31(14) . . ? O1 C19 C20 102.23(13) . . ? C21 C19 C20 110.39(17) . . ? O1 C19 C22 111.28(14) . . ? C21 C19 C22 111.79(17) . . ? C20 C19 C22 112.39(19) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? H20C C20 H20B 109.5 . . ? C19 C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C21 H21A 109.5 . . ? H21B C21 H21A 109.5 . . ? H21C C21 H21A 109.5 . . ? C19 C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C19 C22 H22A 109.5 . . ? H22B C22 H22A 109.5 . . ? H22C C22 H22A 109.5 . . ? 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 C18 N1 C1 C2 114.07(14) . . . . ? C11 N1 C1 C2 -65.67(15) . . . . ? N1 C1 C2 C3 49.84(14) . . . . ? C4 N2 C3 C10 1.42(16) . . . . ? C4 N2 C3 C2 -175.68(13) . . . . ? C1 C2 C3 C10 -19.75(18) . . . . ? C1 C2 C3 N2 156.92(13) . . . . ? C3 N2 C4 C5 176.55(16) . . . . ? C3 N2 C4 C9 -0.99(16) . . . . ? N2 C4 C5 C6 -177.57(16) . . . . ? C9 C4 C5 C6 -0.3(2) . . . . ? C4 C5 C6 C7 -1.2(3) . . . . ? C5 C6 C7 C8 1.4(3) . . . . ? C6 C7 C8 C9 0.0(2) . . . . ? C7 C8 C9 C4 -1.4(2) . . . . ? C7 C8 C9 C10 177.48(16) . . . . ? N2 C4 C9 C8 179.43(12) . . . . ? C5 C4 C9 C8 1.6(2) . . . . ? N2 C4 C9 C10 0.22(15) . . . . ? C5 C4 C9 C10 -177.57(14) . . . . ? N2 C3 C10 C9 -1.25(16) . . . . ? C2 C3 C10 C9 175.85(13) . . . . ? N2 C3 C10 C11 -179.41(12) . . . . ? C2 C3 C10 C11 -2.3(2) . . . . ? C8 C9 C10 C3 -178.40(15) . . . . ? C4 C9 C10 C3 0.62(15) . . . . ? C8 C9 C10 C11 -0.4(3) . . . . ? C4 C9 C10 C11 178.67(13) . . . . ? C18 N1 C11 C10 -139.83(13) . . . . ? C1 N1 C11 C10 39.90(16) . . . . ? C18 N1 C11 C12 95.73(15) . . . . ? C1 N1 C11 C12 -84.54(14) . . . . ? C3 C10 C11 N1 -5.91(18) . . . . ? C9 C10 C11 N1 176.33(13) . . . . ? C3 C10 C11 C12 116.87(15) . . . . ? C9 C10 C11 C12 -60.88(18) . . . . ? N1 C11 C12 C13 84.35(15) . . . . ? C10 C11 C12 C13 -36.73(17) . . . . ? N1 C11 C12 C17 -95.25(14) . . . . ? C10 C11 C12 C17 143.68(13) . . . . ? C17 C12 C13 C14 0.7(2) . . . . ? C11 C12 C13 C14 -178.92(12) . . . . ? C12 C13 C14 C15 -1.7(2) . . . . ? C13 C14 C15 C16 1.5(2) . . . . ? C13 C14 C15 Br1 -176.94(11) . . . . ? C14 C15 C16 C17 -0.3(2) . . . . ? Br1 C15 C16 C17 178.16(12) . . . . ? C15 C16 C17 C12 -0.8(2) . . . . ? C13 C12 C17 C16 0.6(2) . . . . ? C11 C12 C17 C16 -179.79(13) . . . . ? C19 O1 C18 O2 1.3(2) . . . . ? C19 O1 C18 N1 -177.73(12) . . . . ? C1 N1 C18 O2 0.4(2) . . . . ? C11 N1 C18 O2 -179.87(13) . . . . ? C1 N1 C18 O1 179.49(12) . . . . ? C11 N1 C18 O1 -0.78(19) . . . . ? C18 O1 C19 C21 65.40(18) . . . . ? C18 O1 C19 C20 -178.04(16) . . . . ? C18 O1 C19 C22 -57.9(2) . . . . ? 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 H2 O2 0.86(2) 2.04(2) 2.8983(17) 176(2) 3_544 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.73 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.371 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.043