Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name A.Bialonska Z.Ciunik _publ_contact_author_name 'Agata Bialonska' _publ_contact_author_address ; Faculty of Chemistry University of Wroclaw 14. F. Curie-Joliot Wroclaw 50-383 POLAND ; _publ_contact_author_email BIALONSK@ETO.WCHUWR.PL _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Intermolecular Hinge - a New Function of the C-H...Pi Hydrogen Bond ; data_1 _database_code_depnum_ccdc_archive 'CCDC 632635' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium bromide dihydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, 2(H2 O), Br' _chemical_formula_sum 'C23 H31 Br N2 O6' _chemical_formula_weight 511.41 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 monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.475(2) _cell_length_b 11.848(3) _cell_length_c 12.856(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.12(3) _cell_angle_gamma 90.00 _cell_volume 1108.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13286 _cell_measurement_theta_min 3.25 _cell_measurement_theta_max 36.64 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 1.897 _exptl_absorpt_correction_type 'numeric analytical' _exptl_absorpt_correction_T_min 0.5483 _exptl_absorpt_correction_T_max 0.7640 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. ; _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 'Kuma KM4CCD' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19972 _diffrn_reflns_av_R_equivalents 0.0671 _diffrn_reflns_av_sigmaI/netI 0.1102 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 35.00 _reflns_number_total 6905 _reflns_number_gt 4355 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-NT [version 5.1], Bruker AXS Inc., Madison, WI, 1999.' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0327P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration rmad loop_ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' 'Toda F, Tanaka K, Ueda H and Oshima T (1985), Isr. J. Chem., 25, 338-345' _refine_ls_abs_structure_Flack -0.013(6) _refine_ls_number_reflns 6905 _refine_ls_number_parameters 289 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.0774 _refine_ls_wR_factor_gt 0.0703 _refine_ls_goodness_of_fit_ref 0.847 _refine_ls_restrained_S_all 0.847 _refine_ls_shift/su_max 0.008 _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 O1 O 0.2674(2) 0.44729(15) 0.24366(15) 0.0188(4) Uani 1 1 d . . . O2 O 0.2968(2) 0.97035(15) 0.71758(13) 0.0163(4) Uani 1 1 d . . . O3 O 0.2131(2) 1.11534(14) 0.56498(14) 0.0183(4) Uani 1 1 d . . . O4 O 0.2890(3) 0.57420(15) 0.58986(14) 0.0222(4) Uani 1 1 d . . . N1 N 0.3333(3) 0.67671(17) 0.44894(17) 0.0128(4) Uani 1 1 d . . . N2 N 0.2969(3) 0.83477(18) 0.11667(16) 0.0161(4) Uani 1 1 d . . . H2 H 0.2963 0.8979 0.0860 0.019 Uiso 1 1 d . . . C1 C 0.3219(3) 0.8161(2) 0.5967(2) 0.0152(5) Uani 1 1 d . . . H1 H 0.3463 0.7613 0.6521 0.018 Uiso 1 1 calc R . . C2 C 0.2914(3) 0.9290(2) 0.6181(2) 0.0146(5) Uani 1 1 d . . . C3 C 0.2524(3) 1.0095(2) 0.5340(2) 0.0150(5) Uani 1 1 d . . . C4 C 0.2551(3) 0.9780(2) 0.4311(2) 0.0142(5) Uani 1 1 d . . . H4 H 0.2342 1.0324 0.3753 0.017 Uiso 1 1 calc R . . C5 C 0.2892(3) 0.8652(2) 0.4096(2) 0.0148(5) Uani 1 1 d . . . C6 C 0.3150(3) 0.7870(2) 0.4909(2) 0.0137(5) Uani 1 1 d . . . C7 C 0.3181(3) 0.8125(2) 0.30734(19) 0.0128(5) Uani 1 1 d . . . C8 C 0.3051(3) 0.6838(2) 0.33067(18) 0.0121(5) Uani 1 1 d . . . H8 H 0.4068 0.6430 0.3078 0.015 Uiso 1 1 calc R . . C9 C 0.2898(3) 0.5801(2) 0.49419(18) 0.0151(5) Uani 1 1 d . . . C10 C 0.2417(4) 0.4787(2) 0.4222(2) 0.0184(5) Uani 1 1 d . . . H10A H 0.1584 0.4301 0.4525 0.022 Uiso 1 1 calc R . . H10B H 0.3560 0.4352 0.4254 0.022 Uiso 1 1 calc R . . C11 C 0.1511(4) 0.4995(2) 0.3039(2) 0.0172(5) Uani 1 1 d . . . H11 H 0.0287 0.4611 0.2867 0.021 Uiso 1 1 calc R . . C12 C 0.1863(4) 0.4399(2) 0.1311(2) 0.0214(6) Uani 1 1 d . . . H12A H 0.0516 0.4313 0.1202 0.026 Uiso 1 1 calc R . . H12B H 0.2343 0.3723 0.1013 0.026 Uiso 1 1 calc R . . C13 C 0.2275(4) 0.5423(2) 0.0732(2) 0.0197(6) Uani 1 1 d . . . H13 H 0.3009 0.5345 0.0223 0.024 Uiso 1 1 calc R . . C14 C 0.1652(4) 0.6438(2) 0.0903(2) 0.0183(6) Uani 1 1 d . . . C15 C 0.2145(4) 0.7468(2) 0.0343(2) 0.0192(5) Uani 1 1 d . . . H15A H 0.1032 0.7776 -0.0144 0.023 Uiso 1 1 calc R . . H15B H 0.3040 0.7265 -0.0087 0.023 Uiso 1 1 calc R . . C16 C 0.4936(3) 0.8065(2) 0.1720(2) 0.0174(5) Uani 1 1 d . . . H16A H 0.5817 0.8489 0.1399 0.021 Uiso 1 1 calc R . . H16B H 0.5176 0.7247 0.1674 0.021 Uiso 1 1 calc R . . C17 C 0.5074(4) 0.8424(2) 0.2870(2) 0.0167(5) Uani 1 1 d . . . H17A H 0.5318 0.9243 0.2960 0.020 Uiso 1 1 calc R . . H17B H 0.6063 0.8006 0.3363 0.020 Uiso 1 1 calc R . . C18 C 0.1225(3) 0.6257(2) 0.28257(19) 0.0131(5) Uani 1 1 d . . . H18 H 0.0347 0.6511 0.3261 0.016 Uiso 1 1 calc R . . C19 C 0.0401(3) 0.6653(2) 0.1670(2) 0.0171(5) Uani 1 1 d . . . H19 H -0.0793 0.6256 0.1397 0.021 Uiso 1 1 calc R . . C20 C 0.0035(3) 0.7911(2) 0.1735(2) 0.0179(5) Uani 1 1 d . . . H20A H -0.0690 0.8056 0.2277 0.021 Uiso 1 1 calc R . . H20B H -0.0675 0.8189 0.1036 0.021 Uiso 1 1 calc R . . C21 C 0.1879(3) 0.8523(2) 0.2040(2) 0.0155(5) Uani 1 1 d . . . H21 H 0.1644 0.9348 0.2102 0.019 Uiso 1 1 calc R . . C22 C 0.3322(4) 0.8905(2) 0.8039(2) 0.0210(6) Uani 1 1 d . . . H22A H 0.3323 0.9295 0.8711 0.031 Uiso 1 1 calc R . . H22B H 0.4522 0.8550 0.8083 0.031 Uiso 1 1 calc R . . H22C H 0.2364 0.8324 0.7911 0.031 Uiso 1 1 calc R . . C23 C 0.1531(4) 1.1951(2) 0.4803(2) 0.0209(6) Uani 1 1 d . . . H23A H 0.1296 1.2681 0.5106 0.031 Uiso 1 1 calc R . . H23B H 0.0399 1.1678 0.4327 0.031 Uiso 1 1 calc R . . H23C H 0.2486 1.2040 0.4399 0.031 Uiso 1 1 calc R . . Br Br 0.36121(3) 1.09631(2) 0.06093(2) 0.02338(7) Uani 1 1 d . . . O1W O 0.7894(3) 1.04046(19) 0.20923(16) 0.0314(5) Uani 1 1 d . . . H11W H 0.6889 1.0768 0.1777 0.047 Uiso 1 1 d . . . H12W H 0.8002 1.0440 0.2788 0.047 Uiso 1 1 d . . . O2W O 0.0671(3) 1.1972(2) 0.2101(2) 0.0465(6) Uani 1 1 d . . . H21W H 0.1487 1.1792 0.1729 0.070 Uiso 1 1 d . . . H22W H -0.0237 1.1481 0.1950 0.070 Uiso 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 O1 0.0189(9) 0.0166(9) 0.0212(10) -0.0049(8) 0.0053(7) -0.0003(7) O2 0.0195(9) 0.0186(9) 0.0112(9) -0.0005(7) 0.0041(7) -0.0005(7) O3 0.0248(9) 0.0141(11) 0.0166(9) -0.0017(7) 0.0061(7) 0.0027(7) O4 0.0333(10) 0.0172(12) 0.0182(9) 0.0081(8) 0.0103(7) 0.0052(8) N1 0.0147(10) 0.0134(10) 0.0109(10) 0.0007(8) 0.0043(8) 0.0014(8) N2 0.0199(11) 0.0175(10) 0.0115(11) 0.0027(8) 0.0045(8) 0.0009(8) C1 0.0145(12) 0.0162(12) 0.0145(12) 0.0027(10) 0.0024(10) 0.0005(9) C2 0.0116(11) 0.0187(12) 0.0140(12) -0.0011(10) 0.0036(9) -0.0016(9) C3 0.0160(12) 0.0121(11) 0.0181(14) -0.0014(10) 0.0063(10) -0.0017(10) C4 0.0138(12) 0.0124(11) 0.0152(13) 0.0007(9) 0.0012(9) -0.0008(9) C5 0.0139(12) 0.0165(12) 0.0143(13) 0.0000(10) 0.0038(9) -0.0003(10) C6 0.0141(12) 0.0113(11) 0.0162(13) -0.0001(9) 0.0047(9) 0.0022(9) C7 0.0150(12) 0.0122(11) 0.0118(12) -0.0001(9) 0.0043(9) -0.0021(9) C8 0.0146(12) 0.0126(11) 0.0088(12) -0.0001(9) 0.0021(9) -0.0012(9) C9 0.0144(10) 0.0144(14) 0.0173(11) 0.0082(11) 0.0051(8) 0.0056(10) C10 0.0210(14) 0.0140(12) 0.0225(14) 0.0040(10) 0.0096(11) 0.0018(10) C11 0.0161(13) 0.0130(12) 0.0239(14) -0.0031(10) 0.0075(10) -0.0040(10) C12 0.0244(14) 0.0190(13) 0.0197(15) -0.0075(11) 0.0026(11) -0.0033(11) C13 0.0197(15) 0.0236(14) 0.0155(14) -0.0056(11) 0.0037(11) -0.0019(11) C14 0.0180(14) 0.0224(13) 0.0117(14) -0.0047(10) -0.0024(11) -0.0008(11) C15 0.0220(14) 0.0229(14) 0.0120(13) -0.0033(10) 0.0024(10) 0.0016(11) C16 0.0176(13) 0.0187(13) 0.0164(13) 0.0019(10) 0.0047(10) -0.0014(10) C17 0.0200(13) 0.0159(12) 0.0139(13) 0.0011(10) 0.0029(10) -0.0032(10) C18 0.0102(11) 0.0165(12) 0.0131(12) -0.0019(9) 0.0039(9) 0.0002(8) C19 0.0104(11) 0.0253(13) 0.0154(13) -0.0007(10) 0.0020(9) -0.0030(10) C20 0.0171(13) 0.0218(13) 0.0144(13) -0.0007(10) 0.0031(10) 0.0056(10) C21 0.0172(12) 0.0154(12) 0.0150(13) 0.0010(10) 0.0058(10) 0.0027(10) C22 0.0240(14) 0.0265(14) 0.0132(13) 0.0012(11) 0.0057(11) -0.0004(11) C23 0.0269(15) 0.0120(12) 0.0242(15) 0.0022(11) 0.0068(12) 0.0018(11) Br 0.02409(12) 0.02307(12) 0.02313(13) 0.00260(15) 0.00570(9) -0.00063(15) O1W 0.0328(12) 0.0395(12) 0.0247(11) -0.0014(9) 0.0122(9) -0.0015(9) O2W 0.0445(15) 0.0460(15) 0.0528(17) -0.0051(12) 0.0189(12) -0.0128(12) _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 O1 C11 1.430(3) . ? O1 C12 1.439(3) . ? O2 C2 1.362(3) . ? O2 C22 1.436(3) . ? O3 C3 1.368(3) . ? O3 C23 1.434(3) . ? O4 C9 1.233(3) . ? N1 C9 1.356(3) . ? N1 C6 1.432(3) . ? N1 C8 1.489(3) . ? N2 C15 1.513(3) . ? N2 C16 1.518(3) . ? N2 C21 1.544(3) . ? N2 H2 0.8451 . ? C1 C6 1.392(4) . ? C1 C2 1.394(4) . ? C1 H1 0.9500 . ? C2 C3 1.421(4) . ? C3 C4 1.380(4) . ? C4 C5 1.400(4) . ? C4 H4 0.9500 . ? C5 C6 1.378(3) . ? C5 C7 1.514(3) . ? C7 C21 1.531(3) . ? C7 C17 1.538(4) . ? C7 C8 1.561(3) . ? C8 C18 1.529(3) . ? C8 H8 1.0000 . ? C9 C10 1.510(4) . ? C10 C11 1.539(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.527(4) . ? C11 H11 1.0000 . ? C12 C13 1.491(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.326(4) . ? C13 H13 0.9500 . ? C14 C15 1.505(4) . ? C14 C19 1.527(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.520(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.546(4) . ? C18 H18 1.0000 . ? C19 C20 1.521(4) . ? C19 H19 1.0000 . ? C20 C21 1.528(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? O1W H11W 0.8814 . ? O1W H12W 0.8805 . ? O2W H21W 0.8822 . ? O2W H22W 0.8810 . ? 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 C11 O1 C12 113.7(2) . . ? C2 O2 C22 116.7(2) . . ? C3 O3 C23 115.8(2) . . ? C9 N1 C6 123.7(2) . . ? C9 N1 C8 119.6(2) . . ? C6 N1 C8 109.27(19) . . ? C15 N2 C16 111.9(2) . . ? C15 N2 C21 113.8(2) . . ? C16 N2 C21 107.69(18) . . ? C15 N2 H2 108.9 . . ? C16 N2 H2 108.4 . . ? C21 N2 H2 105.8 . . ? C6 C1 C2 117.3(2) . . ? C6 C1 H1 121.4 . . ? C2 C1 H1 121.4 . . ? O2 C2 C1 124.0(2) . . ? O2 C2 C3 115.5(2) . . ? C1 C2 C3 120.6(2) . . ? O3 C3 C4 125.3(2) . . ? O3 C3 C2 114.5(2) . . ? C4 C3 C2 120.2(2) . . ? C3 C4 C5 119.3(2) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 119.5(2) . . ? C6 C5 C7 111.0(2) . . ? C4 C5 C7 129.3(2) . . ? C5 C6 C1 122.8(2) . . ? C5 C6 N1 109.7(2) . . ? C1 C6 N1 127.5(2) . . ? C5 C7 C21 116.0(2) . . ? C5 C7 C17 111.7(2) . . ? C21 C7 C17 102.12(19) . . ? C5 C7 C8 102.07(19) . . ? C21 C7 C8 114.3(2) . . ? C17 C7 C8 110.9(2) . . ? N1 C8 C18 107.09(19) . . ? N1 C8 C7 104.52(18) . . ? C18 C8 C7 116.8(2) . . ? N1 C8 H8 109.4 . . ? C18 C8 H8 109.4 . . ? C7 C8 H8 109.4 . . ? O4 C9 N1 122.1(2) . . ? O4 C9 C10 120.7(2) . . ? N1 C9 C10 117.1(2) . . ? C9 C10 C11 117.9(2) . . ? C9 C10 H10A 107.8 . . ? C11 C10 H10A 107.8 . . ? C9 C10 H10B 107.8 . . ? C11 C10 H10B 107.8 . . ? H10A C10 H10B 107.2 . . ? O1 C11 C18 113.8(2) . . ? O1 C11 C10 106.3(2) . . ? C18 C11 C10 110.3(2) . . ? O1 C11 H11 108.8 . . ? C18 C11 H11 108.8 . . ? C10 C11 H11 108.8 . . ? O1 C12 C13 111.4(2) . . ? O1 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? O1 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C14 C13 C12 122.4(3) . . ? C14 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? C13 C14 C15 121.6(2) . . ? C13 C14 C19 123.2(2) . . ? C15 C14 C19 115.2(2) . . ? C14 C15 N2 109.2(2) . . ? C14 C15 H15A 109.8 . . ? N2 C15 H15A 109.8 . . ? C14 C15 H15B 109.8 . . ? N2 C15 H15B 109.8 . . ? H15A C15 H15B 108.3 . . ? N2 C16 C17 103.8(2) . . ? N2 C16 H16A 111.0 . . ? C17 C16 H16A 111.0 . . ? N2 C16 H16B 111.0 . . ? C17 C16 H16B 111.0 . . ? H16A C16 H16B 109.0 . . ? C16 C17 C7 103.8(2) . . ? C16 C17 H17A 111.0 . . ? C7 C17 H17A 111.0 . . ? C16 C17 H17B 111.0 . . ? C7 C17 H17B 111.0 . . ? H17A C17 H17B 109.0 . . ? C11 C18 C8 107.0(2) . . ? C11 C18 C19 118.6(2) . . ? C8 C18 C19 112.1(2) . . ? C11 C18 H18 106.1 . . ? C8 C18 H18 106.1 . . ? C19 C18 H18 106.1 . . ? C20 C19 C14 110.1(2) . . ? C20 C19 C18 106.4(2) . . ? C14 C19 C18 113.7(2) . . ? C20 C19 H19 108.9 . . ? C14 C19 H19 108.9 . . ? C18 C19 H19 108.9 . . ? C19 C20 C21 108.4(2) . . ? C19 C20 H20A 110.0 . . ? C21 C20 H20A 110.0 . . ? C19 C20 H20B 110.0 . . ? C21 C20 H20B 110.0 . . ? H20A C20 H20B 108.4 . . ? C20 C21 C7 115.8(2) . . ? C20 C21 N2 110.1(2) . . ? C7 C21 N2 104.66(19) . . ? C20 C21 H21 108.7 . . ? C7 C21 H21 108.7 . . ? N2 C21 H21 108.7 . . ? O2 C22 H22A 109.5 . . ? O2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O3 C23 H23A 109.5 . . ? O3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? H11W O1W H12W 108.4 . . ? H21W O2W H22W 108.3 . . ? 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 C22 O2 C2 C1 -1.4(3) . . . . ? C22 O2 C2 C3 178.7(2) . . . . ? C6 C1 C2 O2 -178.9(2) . . . . ? C6 C1 C2 C3 1.0(4) . . . . ? C23 O3 C3 C4 6.4(4) . . . . ? C23 O3 C3 C2 -173.3(2) . . . . ? O2 C2 C3 O3 -4.4(3) . . . . ? C1 C2 C3 O3 175.8(2) . . . . ? O2 C2 C3 C4 175.9(2) . . . . ? C1 C2 C3 C4 -4.0(4) . . . . ? O3 C3 C4 C5 -177.0(2) . . . . ? C2 C3 C4 C5 2.7(4) . . . . ? C3 C4 C5 C6 1.5(4) . . . . ? C3 C4 C5 C7 -173.2(2) . . . . ? C4 C5 C6 C1 -4.7(4) . . . . ? C7 C5 C6 C1 170.9(2) . . . . ? C4 C5 C6 N1 175.6(2) . . . . ? C7 C5 C6 N1 -8.8(3) . . . . ? C2 C1 C6 C5 3.4(4) . . . . ? C2 C1 C6 N1 -176.9(2) . . . . ? C9 N1 C6 C5 -153.4(2) . . . . ? C8 N1 C6 C5 -3.9(3) . . . . ? C9 N1 C6 C1 26.8(4) . . . . ? C8 N1 C6 C1 176.4(2) . . . . ? C6 C5 C7 C21 141.9(2) . . . . ? C4 C5 C7 C21 -43.1(4) . . . . ? C6 C5 C7 C17 -101.7(2) . . . . ? C4 C5 C7 C17 73.4(3) . . . . ? C6 C5 C7 C8 16.9(3) . . . . ? C4 C5 C7 C8 -168.0(2) . . . . ? C9 N1 C8 C18 40.7(3) . . . . ? C6 N1 C8 C18 -110.3(2) . . . . ? C9 N1 C8 C7 165.2(2) . . . . ? C6 N1 C8 C7 14.2(2) . . . . ? C5 C7 C8 N1 -18.0(2) . . . . ? C21 C7 C8 N1 -144.1(2) . . . . ? C17 C7 C8 N1 101.1(2) . . . . ? C5 C7 C8 C18 100.1(2) . . . . ? C21 C7 C8 C18 -26.0(3) . . . . ? C17 C7 C8 C18 -140.8(2) . . . . ? C6 N1 C9 O4 -24.3(4) . . . . ? C8 N1 C9 O4 -171.0(2) . . . . ? C6 N1 C9 C10 155.7(2) . . . . ? C8 N1 C9 C10 9.1(3) . . . . ? O4 C9 C10 C11 149.7(2) . . . . ? N1 C9 C10 C11 -30.4(3) . . . . ? C12 O1 C11 C18 -69.5(3) . . . . ? C12 O1 C11 C10 168.9(2) . . . . ? C9 C10 C11 O1 122.5(2) . . . . ? C9 C10 C11 C18 -1.4(3) . . . . ? C11 O1 C12 C13 89.4(3) . . . . ? O1 C12 C13 C14 -64.9(4) . . . . ? C12 C13 C14 C15 177.5(2) . . . . ? C12 C13 C14 C19 -2.4(5) . . . . ? C13 C14 C15 N2 -125.4(3) . . . . ? C19 C14 C15 N2 54.6(3) . . . . ? C16 N2 C15 C14 76.2(3) . . . . ? C21 N2 C15 C14 -46.2(3) . . . . ? C15 N2 C16 C17 -142.2(2) . . . . ? C21 N2 C16 C17 -16.4(2) . . . . ? N2 C16 C17 C7 36.6(2) . . . . ? C5 C7 C17 C16 -167.3(2) . . . . ? C21 C7 C17 C16 -42.7(2) . . . . ? C8 C7 C17 C16 79.5(2) . . . . ? O1 C11 C18 C8 -69.8(3) . . . . ? C10 C11 C18 C8 49.6(3) . . . . ? O1 C11 C18 C19 58.1(3) . . . . ? C10 C11 C18 C19 177.5(2) . . . . ? N1 C8 C18 C11 -70.4(2) . . . . ? C7 C8 C18 C11 172.9(2) . . . . ? N1 C8 C18 C19 157.9(2) . . . . ? C7 C8 C18 C19 41.2(3) . . . . ? C13 C14 C19 C20 176.5(3) . . . . ? C15 C14 C19 C20 -3.4(3) . . . . ? C13 C14 C19 C18 57.2(4) . . . . ? C15 C14 C19 C18 -122.7(2) . . . . ? C11 C18 C19 C20 172.2(2) . . . . ? C8 C18 C19 C20 -62.2(3) . . . . ? C11 C18 C19 C14 -66.4(3) . . . . ? C8 C18 C19 C14 59.1(3) . . . . ? C14 C19 C20 C21 -55.0(3) . . . . ? C18 C19 C20 C21 68.6(3) . . . . ? C19 C20 C21 C7 -55.9(3) . . . . ? C19 C20 C21 N2 62.6(3) . . . . ? C5 C7 C21 C20 -85.1(3) . . . . ? C17 C7 C21 C20 153.2(2) . . . . ? C8 C7 C21 C20 33.3(3) . . . . ? C5 C7 C21 N2 153.5(2) . . . . ? C17 C7 C21 N2 31.8(2) . . . . ? C8 C7 C21 N2 -88.1(2) . . . . ? C15 N2 C21 C20 -10.4(3) . . . . ? C16 N2 C21 C20 -135.0(2) . . . . ? C15 N2 C21 C7 114.7(2) . . . . ? C16 N2 C21 C7 -9.9(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 Br 0.85 2.44 3.241(2) 159.3 . O1W H11W Br 0.88 2.58 3.398(2) 155.6 . O1W H12W O4 0.88 1.98 2.804(3) 154.4 2_656 O2W H21W Br 0.88 2.57 3.443(3) 170.9 . O2W H22W O1W 0.88 1.93 2.783(3) 162.3 1_455 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 35.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.938 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.085