data_q62b _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H31 Br N2 O2' _chemical_formula_weight 435.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.5683(4) _cell_length_b 17.2000(6) _cell_length_c 9.5705(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.0620(10) _cell_angle_gamma 90.00 _cell_volume 2068.55(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9836 _cell_measurement_theta_min 3.52 _cell_measurement_theta_max 68.94 _exptl_crystal_description 'Irregular chunk' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 2.853 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker MicroStar microfocus rotating anode' _diffrn_radiation_monochromator 'Helios multilayer optics' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 22290 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.36 _diffrn_reflns_theta_max 69.34 _reflns_number_total 3785 _reflns_number_gt 3714 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0288P)^2^+1.1802P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3785 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0239 _refine_ls_R_factor_gt 0.0234 _refine_ls_wR_factor_ref 0.0600 _refine_ls_wR_factor_gt 0.0597 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 Br Br -0.561455(12) 0.089393(9) 0.126028(16) 0.02507(7) Uani 1 1 d . . . O1 O 0.05384(8) 0.24506(6) 0.06931(10) 0.0185(2) Uani 1 1 d . . . O2 O -0.07958(8) 0.22724(6) -0.09050(10) 0.0225(2) Uani 1 1 d . . . N1 N 0.21232(9) 0.38984(7) 0.17373(13) 0.0188(2) Uani 1 1 d . . . N2 N -0.09954(10) 0.19588(7) 0.13960(13) 0.0184(2) Uani 1 1 d . . . H2N H -0.0752(15) 0.2063(11) 0.215(2) 0.022(5) Uiso 1 1 d . . . C1 C 0.31001(11) 0.38906(9) 0.08945(15) 0.0203(3) Uani 1 1 d . . . H1 H 0.3276 0.4439 0.0643 0.024 Uiso 1 1 calc R . . C2 C 0.28973(12) 0.34338(9) -0.04663(15) 0.0223(3) Uani 1 1 d . . . H2 H 0.3572 0.3357 -0.0987 0.027 Uiso 1 1 calc R . . C3 C 0.23603(12) 0.26445(9) -0.01449(16) 0.0222(3) Uani 1 1 d . . . H3A H 0.2613 0.2232 -0.0780 0.027 Uiso 1 1 calc R . . H3B H 0.2505 0.2484 0.0834 0.027 Uiso 1 1 calc R . . C4 C 0.11703(11) 0.28105(9) -0.03943(15) 0.0204(3) Uani 1 1 d . . . H4 H 0.0950 0.2581 -0.1315 0.024 Uiso 1 1 calc R . . C5 C 0.10733(12) 0.36976(9) -0.04954(15) 0.0219(3) Uani 1 1 d . . . H5 H 0.0408 0.3850 -0.1015 0.026 Uiso 1 1 calc R . . C6 C 0.11890(12) 0.41523(8) 0.08832(16) 0.0210(3) Uani 1 1 d . . . H6 H 0.1315 0.4708 0.0627 0.025 Uiso 1 1 calc R . . C7 C 0.01828(13) 0.41356(9) 0.17565(18) 0.0256(3) Uani 1 1 d . . . H7A H -0.0429 0.4318 0.1178 0.031 Uiso 1 1 calc R . . H7B H 0.0036 0.3594 0.2046 0.031 Uiso 1 1 calc R . . C8 C 0.02942(13) 0.46477(10) 0.30539(18) 0.0308(4) Uani 1 1 d . . . H8A H 0.0335 0.5201 0.2774 0.037 Uiso 1 1 calc R . . H8B H -0.0335 0.4581 0.3649 0.037 Uiso 1 1 calc R . . C9 C 0.12983(14) 0.44216(9) 0.38711(17) 0.0289(3) Uani 1 1 d . . . H9A H 0.1414 0.4790 0.4654 0.035 Uiso 1 1 calc R . . H9B H 0.1211 0.3895 0.4269 0.035 Uiso 1 1 calc R . . C10 C 0.22574(13) 0.44320(9) 0.29296(16) 0.0245(3) Uani 1 1 d . . . H10A H 0.2366 0.4967 0.2577 0.029 Uiso 1 1 calc R . . H10B H 0.2900 0.4281 0.3480 0.029 Uiso 1 1 calc R . . C11 C 0.20575(13) 0.38546(9) -0.13735(16) 0.0252(3) Uani 1 1 d . . . H11A H 0.2209 0.4418 -0.1454 0.030 Uiso 1 1 calc R . . H11B H 0.1990 0.3623 -0.2318 0.030 Uiso 1 1 calc R . . C12 C 0.40690(12) 0.35373(9) 0.16663(17) 0.0241(3) Uani 1 1 d . . . H12A H 0.3983 0.3599 0.2687 0.029 Uiso 1 1 calc R . . H12B H 0.4108 0.2974 0.1459 0.029 Uiso 1 1 calc R . . C13 C 0.51063(12) 0.39319(9) 0.12260(16) 0.0221(3) Uani 1 1 d . . . H13A H 0.5053 0.4065 0.0221 0.027 Uiso 1 1 calc R . . H13B H 0.5198 0.4422 0.1757 0.027 Uiso 1 1 calc R . . C14 C 0.60798(12) 0.34199(9) 0.14762(16) 0.0227(3) Uani 1 1 d . . . H14A H 0.6050 0.2977 0.0816 0.027 Uiso 1 1 calc R . . H14B H 0.6057 0.3206 0.2435 0.027 Uiso 1 1 calc R . . C15 C 0.71302(12) 0.38484(10) 0.12982(17) 0.0262(3) Uani 1 1 d . . . H15A H 0.7723 0.3486 0.1452 0.039 Uiso 1 1 calc R . . H15B H 0.7182 0.4273 0.1978 0.039 Uiso 1 1 calc R . . H15C H 0.7161 0.4061 0.0350 0.039 Uiso 1 1 calc R . . C16 C -0.04483(11) 0.22339(8) 0.02859(14) 0.0169(3) Uani 1 1 d . . . C17 C -0.20587(11) 0.16894(8) 0.13316(14) 0.0173(3) Uani 1 1 d . . . C18 C -0.25073(12) 0.13581(9) 0.01297(15) 0.0204(3) Uani 1 1 d . . . H18 H -0.2094 0.1304 -0.0686 0.024 Uiso 1 1 calc R . . C19 C -0.35572(12) 0.11073(9) 0.01229(15) 0.0211(3) Uani 1 1 d . . . H19 H -0.3865 0.0883 -0.0696 0.025 Uiso 1 1 calc R . . C20 C -0.41526(11) 0.11867(8) 0.13176(16) 0.0197(3) Uani 1 1 d . . . C21 C -0.37130(12) 0.14924(9) 0.25297(15) 0.0209(3) Uani 1 1 d . . . H21 H -0.4124 0.1531 0.3350 0.025 Uiso 1 1 calc R . . C22 C -0.26613(12) 0.17439(8) 0.25369(15) 0.0199(3) Uani 1 1 d . . . H22 H -0.2352 0.1954 0.3367 0.024 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 Br 0.01908(10) 0.02888(11) 0.02724(10) -0.00062(6) 0.00073(6) -0.00427(6) O1 0.0180(5) 0.0219(5) 0.0156(5) 0.0012(4) 0.0000(4) -0.0030(4) O2 0.0215(5) 0.0305(6) 0.0154(5) 0.0033(4) -0.0012(4) -0.0031(4) N1 0.0183(6) 0.0182(6) 0.0198(6) -0.0014(5) 0.0004(5) 0.0000(5) N2 0.0198(6) 0.0234(6) 0.0120(6) -0.0005(5) -0.0020(5) -0.0023(5) C1 0.0192(7) 0.0192(7) 0.0225(7) 0.0016(6) 0.0016(6) -0.0023(6) C2 0.0208(7) 0.0245(8) 0.0218(7) -0.0006(6) 0.0054(6) -0.0030(6) C3 0.0207(7) 0.0213(7) 0.0249(7) -0.0028(6) 0.0038(6) -0.0010(6) C4 0.0211(7) 0.0237(8) 0.0165(7) 0.0008(5) 0.0028(5) -0.0043(6) C5 0.0207(7) 0.0243(8) 0.0204(7) 0.0050(6) -0.0018(6) -0.0016(6) C6 0.0206(7) 0.0173(7) 0.0251(8) 0.0033(5) 0.0000(6) 0.0011(5) C7 0.0208(8) 0.0239(8) 0.0321(9) 0.0006(6) 0.0026(6) 0.0031(6) C8 0.0308(8) 0.0237(8) 0.0381(9) -0.0045(7) 0.0111(7) 0.0036(7) C9 0.0380(9) 0.0226(8) 0.0264(8) -0.0060(6) 0.0070(7) -0.0014(7) C10 0.0279(8) 0.0207(8) 0.0249(8) -0.0035(6) -0.0002(6) -0.0015(6) C11 0.0283(8) 0.0274(8) 0.0198(7) 0.0035(6) 0.0023(6) -0.0067(6) C12 0.0204(7) 0.0236(8) 0.0284(8) 0.0027(6) 0.0004(6) -0.0006(6) C13 0.0220(7) 0.0207(7) 0.0238(7) -0.0013(6) 0.0003(6) -0.0011(6) C14 0.0225(7) 0.0214(7) 0.0241(7) -0.0005(6) -0.0004(6) -0.0009(6) C15 0.0213(7) 0.0278(8) 0.0297(8) 0.0012(6) 0.0005(6) -0.0007(6) C16 0.0184(7) 0.0149(6) 0.0174(7) -0.0007(5) -0.0002(5) 0.0013(5) C17 0.0190(7) 0.0153(7) 0.0176(7) 0.0022(5) -0.0003(5) 0.0003(5) C18 0.0239(7) 0.0205(7) 0.0168(7) -0.0003(5) 0.0020(5) -0.0016(6) C19 0.0246(7) 0.0203(7) 0.0183(7) -0.0006(5) -0.0019(6) -0.0028(6) C20 0.0182(7) 0.0174(7) 0.0234(7) 0.0030(5) -0.0004(5) -0.0010(5) C21 0.0227(7) 0.0214(7) 0.0186(7) 0.0010(5) 0.0037(6) 0.0000(6) C22 0.0230(7) 0.0213(7) 0.0153(6) 0.0000(5) -0.0009(5) -0.0011(6) _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 Br C20 1.9051(14) . ? O1 C16 1.3457(17) . ? O1 C4 1.4586(16) . ? O2 C16 1.2148(18) . ? N1 C10 1.4716(19) . ? N1 C1 1.4816(18) . ? N1 C6 1.4840(19) . ? N2 C16 1.3610(19) . ? N2 C17 1.4147(19) . ? N2 H2N 0.80(2) . ? C1 C12 1.538(2) . ? C1 C2 1.538(2) . ? C1 H1 1.0000 . ? C2 C11 1.535(2) . ? C2 C3 1.549(2) . ? C2 H2 1.0000 . ? C3 C4 1.537(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.534(2) . ? C4 H4 1.0000 . ? C5 C11 1.532(2) . ? C5 C6 1.538(2) . ? C5 H5 1.0000 . ? C6 C7 1.529(2) . ? C6 H6 1.0000 . ? C7 C8 1.527(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.523(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.518(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.536(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.523(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.524(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C17 C18 1.393(2) . ? C17 C22 1.395(2) . ? C18 C19 1.388(2) . ? C18 H18 0.9500 . ? C19 C20 1.385(2) . ? C19 H19 0.9500 . ? C20 C21 1.380(2) . ? C21 C22 1.391(2) . ? C21 H21 0.9500 . ? C22 H22 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 C16 O1 C4 114.96(11) . . ? C10 N1 C1 110.10(11) . . ? C10 N1 C6 108.77(12) . . ? C1 N1 C6 110.97(11) . . ? C16 N2 C17 124.77(12) . . ? C16 N2 H2N 115.9(13) . . ? C17 N2 H2N 117.3(13) . . ? N1 C1 C12 113.51(12) . . ? N1 C1 C2 109.85(12) . . ? C12 C1 C2 108.80(12) . . ? N1 C1 H1 108.2 . . ? C12 C1 H1 108.2 . . ? C2 C1 H1 108.2 . . ? C11 C2 C1 109.84(12) . . ? C11 C2 C3 103.17(12) . . ? C1 C2 C3 110.21(12) . . ? C11 C2 H2 111.1 . . ? C1 C2 H2 111.1 . . ? C3 C2 H2 111.1 . . ? C4 C3 C2 103.45(12) . . ? C4 C3 H3A 111.1 . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3B 111.1 . . ? C2 C3 H3B 111.1 . . ? H3A C3 H3B 109.0 . . ? O1 C4 C5 115.06(12) . . ? O1 C4 C3 110.58(12) . . ? C5 C4 C3 105.70(12) . . ? O1 C4 H4 108.4 . . ? C5 C4 H4 108.4 . . ? C3 C4 H4 108.4 . . ? C11 C5 C4 98.39(12) . . ? C11 C5 C6 108.45(12) . . ? C4 C5 C6 116.46(12) . . ? C11 C5 H5 110.9 . . ? C4 C5 H5 110.9 . . ? C6 C5 H5 110.9 . . ? N1 C6 C7 110.33(12) . . ? N1 C6 C5 112.59(12) . . ? C7 C6 C5 113.16(13) . . ? N1 C6 H6 106.8 . . ? C7 C6 H6 106.8 . . ? C5 C6 H6 106.8 . . ? C8 C7 C6 111.68(13) . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C9 C8 C7 109.45(13) . . ? C9 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? C9 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? C10 C9 C8 110.59(13) . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? N1 C10 C9 111.84(12) . . ? N1 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? N1 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C5 C11 C2 99.22(11) . . ? C5 C11 H11A 111.9 . . ? C2 C11 H11A 111.9 . . ? C5 C11 H11B 111.9 . . ? C2 C11 H11B 111.9 . . ? H11A C11 H11B 109.6 . . ? C13 C12 C1 111.24(12) . . ? C13 C12 H12A 109.4 . . ? C1 C12 H12A 109.4 . . ? C13 C12 H12B 109.4 . . ? C1 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C14 C13 C12 112.64(13) . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13A 109.1 . . ? C14 C13 H13B 109.1 . . ? C12 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C13 C14 C15 113.44(13) . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14B 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O2 C16 O1 124.74(13) . . ? O2 C16 N2 124.98(13) . . ? O1 C16 N2 110.27(12) . . ? C18 C17 C22 119.51(13) . . ? C18 C17 N2 122.50(13) . . ? C22 C17 N2 117.96(13) . . ? C19 C18 C17 120.06(13) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 119.58(14) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C21 C20 C19 121.18(13) . . ? C21 C20 Br 119.73(11) . . ? C19 C20 Br 119.07(11) . . ? C20 C21 C22 119.24(13) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C21 C22 C17 120.37(13) . . ? C21 C22 H22 119.8 . . ? C17 C22 H22 119.8 . . ? 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 C10 N1 C1 C12 66.65(15) . . . . ? C6 N1 C1 C12 -172.88(12) . . . . ? C10 N1 C1 C2 -171.31(12) . . . . ? C6 N1 C1 C2 -50.83(15) . . . . ? N1 C1 C2 C11 64.60(15) . . . . ? C12 C1 C2 C11 -170.59(12) . . . . ? N1 C1 C2 C3 -48.42(16) . . . . ? C12 C1 C2 C3 76.39(14) . . . . ? C11 C2 C3 C4 -20.82(14) . . . . ? C1 C2 C3 C4 96.41(14) . . . . ? C16 O1 C4 C5 90.48(14) . . . . ? C16 O1 C4 C3 -149.88(12) . . . . ? C2 C3 C4 O1 -138.00(12) . . . . ? C2 C3 C4 C5 -12.86(14) . . . . ? O1 C4 C5 C11 163.68(12) . . . . ? C3 C4 C5 C11 41.37(14) . . . . ? O1 C4 C5 C6 48.17(17) . . . . ? C3 C4 C5 C6 -74.14(15) . . . . ? C10 N1 C6 C7 -60.30(15) . . . . ? C1 N1 C6 C7 178.44(12) . . . . ? C10 N1 C6 C5 172.22(12) . . . . ? C1 N1 C6 C5 50.96(15) . . . . ? C11 C5 C6 N1 -62.38(15) . . . . ? C4 C5 C6 N1 47.37(17) . . . . ? C11 C5 C6 C7 171.66(12) . . . . ? C4 C5 C6 C7 -78.60(16) . . . . ? N1 C6 C7 C8 57.64(16) . . . . ? C5 C6 C7 C8 -175.20(13) . . . . ? C6 C7 C8 C9 -53.31(18) . . . . ? C7 C8 C9 C10 53.01(17) . . . . ? C1 N1 C10 C9 -176.61(13) . . . . ? C6 N1 C10 C9 61.60(16) . . . . ? C8 C9 C10 N1 -58.68(17) . . . . ? C4 C5 C11 C2 -53.49(13) . . . . ? C6 C5 C11 C2 68.11(14) . . . . ? C1 C2 C11 C5 -70.76(14) . . . . ? C3 C2 C11 C5 46.73(14) . . . . ? N1 C1 C12 C13 -147.05(12) . . . . ? C2 C1 C12 C13 90.32(15) . . . . ? C1 C12 C13 C14 -156.93(13) . . . . ? C12 C13 C14 C15 -169.54(13) . . . . ? C4 O1 C16 O2 5.06(19) . . . . ? C4 O1 C16 N2 -175.54(11) . . . . ? C17 N2 C16 O2 -1.2(2) . . . . ? C17 N2 C16 O1 179.41(12) . . . . ? C16 N2 C17 C18 28.9(2) . . . . ? C16 N2 C17 C22 -152.70(14) . . . . ? C22 C17 C18 C19 2.0(2) . . . . ? N2 C17 C18 C19 -179.65(13) . . . . ? C17 C18 C19 C20 -0.2(2) . . . . ? C18 C19 C20 C21 -1.7(2) . . . . ? C18 C19 C20 Br 176.50(11) . . . . ? C19 C20 C21 C22 1.8(2) . . . . ? Br C20 C21 C22 -176.48(11) . . . . ? C20 C21 C22 C17 0.1(2) . . . . ? C18 C17 C22 C21 -2.0(2) . . . . ? N2 C17 C22 C21 179.59(13) . . . . ? 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 O2 0.80(2) 2.18(2) 2.9085(16) 150.6(18) 4_566 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 66.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.322 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.046