# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry, 1999 # CCDC Number: 182/1310 data_ic6143 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C22 H25 N O6' _chemical_formula_weight 399.43 _chemical_melting_point ? _chemical_compound_source ? 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' _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 10.6487(14) _cell_length_b 22.172(3) _cell_length_c 8.588(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.726(13) _cell_angle_gamma 90.00 _cell_volume 2017.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.35 _cell_measurement_theta_max 11.6 _exptl_crystal_description prism _exptl_crystal_colour colorles _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.025 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method ? _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type psi _exptl_absorpt_correction_T_min 0.927 _exptl_absorpt_correction_T_max 0.9743 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Enraf-Nonius CAD4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 60 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3545 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3545 _reflns_number_observed 2267 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Enraf-Nonius CAD4' _computing_cell_refinement 'Enraf-Nonius CAD4' _computing_data_reduction 'NRCSDP DATARD2' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0767P)^2^+0.0989P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0049(13) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3545 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_obs 0.0430 _refine_ls_wR_factor_all 0.1403 _refine_ls_wR_factor_obs 0.1261 _refine_ls_goodness_of_fit_all 1.068 _refine_ls_goodness_of_fit_obs 1.225 _refine_ls_restrained_S_all 1.068 _refine_ls_restrained_S_obs 1.225 _refine_ls_shift/esd_max 0.013 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.2108(2) 0.71537(7) 0.9304(2) 0.0538(5) Uani 1 d . . O2 O 0.3574(2) 0.50082(8) 1.2868(2) 0.0628(5) Uani 1 d . . O3 O 0.32782(14) 0.60171(7) 0.9203(2) 0.0431(4) Uani 1 d . . O4 O 0.11783(14) 0.59162(7) 0.8179(2) 0.0393(4) Uani 1 d . . O5 O -0.2620(2) 0.59533(8) 1.0027(2) 0.0641(5) Uani 1 d . . O6 O -0.29800(15) 0.68669(8) 0.8969(2) 0.0574(5) Uani 1 d . . N1 N -0.0078(2) 0.53740(8) 1.2401(2) 0.0362(4) Uani 1 d . . H1A H 0.0108(2) 0.50029(8) 1.2604(2) 0.043 Uiso 1 calc R . C1 C 0.2430(2) 0.58955(10) 1.2315(2) 0.0367(5) Uani 1 d . . C2 C 0.2128(2) 0.64542(10) 1.2674(2) 0.0377(5) Uani 1 d . . H2A H 0.2487(2) 0.66486(10) 1.3570(2) 0.045 Uiso 1 calc R . C3 C 0.1163(2) 0.67510(9) 1.1527(2) 0.0357(5) Uani 1 d . . H3A H 0.1007(2) 0.71694(9) 1.1821(2) 0.043 Uiso 1 calc R . C4 C 0.1802(2) 0.67169(9) 1.0015(3) 0.0363(5) Uani 1 d . . C5 C 0.2026(2) 0.60590(9) 0.9511(2) 0.0337(5) Uani 1 d . . C6 C 0.1686(2) 0.56508(9) 1.0860(2) 0.0311(5) Uani 1 d . . H6A H 0.1915(2) 0.52306(9) 1.0677(2) 0.037 Uiso 1 calc R . C7 C 0.0265(2) 0.57071(8) 1.1032(2) 0.0307(5) Uani 1 d . . H7A H -0.0225(2) 0.55573(8) 1.0084(2) 0.037 Uiso 1 calc R . C8 C -0.0083(2) 0.63772(9) 1.1322(2) 0.0318(5) Uani 1 d . . C9 C -0.0739(2) 0.63414(9) 1.2809(2) 0.0344(5) Uani 1 d . . C10 C -0.1351(2) 0.67822(10) 1.3554(3) 0.0453(6) Uani 1 d . . H10A H -0.1362(2) 0.71774(10) 1.3189(3) 0.054 Uiso 1 calc R . C11 C -0.1958(2) 0.66309(11) 1.4866(3) 0.0549(7) Uani 1 d . . H11A H -0.2359(2) 0.69279(11) 1.5400(3) 0.066 Uiso 1 calc R . C12 C -0.1964(2) 0.60415(12) 1.5370(3) 0.0524(7) Uani 1 d . . H12A H -0.2379(2) 0.59443(12) 1.6239(3) 0.063 Uiso 1 calc R . C13 C -0.1363(2) 0.55901(11) 1.4609(3) 0.0436(6) Uani 1 d . . H13A H -0.1374(2) 0.51929(11) 1.4956(3) 0.052 Uiso 1 calc R . C14 C -0.0745(2) 0.57447(9) 1.3319(2) 0.0338(5) Uani 1 d . . C15 C 0.3452(2) 0.55359(11) 1.3170(3) 0.0434(6) Uani 1 d . . C16 C 0.4360(3) 0.58444(15) 1.4365(4) 0.0809(10) Uani 1 d . . H16A H 0.4963(3) 0.55566(15) 1.4818(4) 0.121 Uiso 1 calc R . H16B H 0.3904(3) 0.60136(15) 1.5170(4) 0.121 Uiso 1 calc R . H16C H 0.4792(3) 0.61601(15) 1.3870(4) 0.121 Uiso 1 calc R . C17 C 0.3679(2) 0.54255(11) 0.8769(3) 0.0587(7) Uani 1 d . . H17A H 0.4552(2) 0.54385(11) 0.8579(3) 0.088 Uiso 1 calc R . H17B H 0.3179(2) 0.52965(11) 0.7836(3) 0.088 Uiso 1 calc R . H17C H 0.3573(2) 0.51469(11) 0.9601(3) 0.088 Uiso 1 calc R . C18 C 0.1378(3) 0.62396(12) 0.6765(3) 0.0564(7) Uani 1 d . . H18A H 0.0764(3) 0.61137(12) 0.5935(3) 0.085 Uiso 1 calc R . H18B H 0.2210(3) 0.61552(12) 0.6482(3) 0.085 Uiso 1 calc R . H18C H 0.1294(3) 0.66648(12) 0.6938(3) 0.085 Uiso 1 calc R . C19 C -0.0929(2) 0.66712(9) 0.9988(3) 0.0379(5) Uani 1 d . . H19A H -0.0965(2) 0.71004(9) 1.0197(3) 0.045 Uiso 1 calc R . H19B H -0.0528(2) 0.66216(9) 0.9030(3) 0.045 Uiso 1 calc R . C20 C -0.2251(2) 0.64404(10) 0.9705(3) 0.0397(5) Uani 1 d . . C21 C -0.4291(2) 0.67169(14) 0.8546(4) 0.0715(9) Uani 1 d . . H21A H -0.4710(2) 0.66351(14) 0.9476(4) 0.086 Uiso 1 calc R . H21B H -0.4359(2) 0.63619(14) 0.7883(4) 0.086 Uiso 1 calc R . C22 C -0.4879(3) 0.7244(2) 0.7694(5) 0.0991(13) Uani 1 d . . H22A H -0.5754(3) 0.7162(2) 0.7391(5) 0.149 Uiso 1 calc R . H22B H -0.4456(3) 0.7320(2) 0.6778(5) 0.149 Uiso 1 calc R . H22C H -0.4806(3) 0.7592(2) 0.8363(5) 0.149 Uiso 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 O1 0.0698(12) 0.0340(9) 0.0598(11) 0.0118(8) 0.0171(9) -0.0067(8) O2 0.0663(12) 0.0503(12) 0.0692(13) 0.0062(9) -0.0069(10) 0.0172(9) O3 0.0388(9) 0.0423(9) 0.0496(10) 0.0042(7) 0.0114(7) -0.0002(7) O4 0.0471(9) 0.0421(9) 0.0286(8) 0.0029(7) 0.0028(6) -0.0070(7) O5 0.0633(12) 0.0442(10) 0.0819(14) 0.0123(10) -0.0076(10) -0.0171(9) O6 0.0376(9) 0.0512(10) 0.0808(13) 0.0182(9) -0.0066(8) -0.0010(8) N1 0.0485(10) 0.0256(9) 0.0358(10) 0.0057(8) 0.0109(8) 0.0019(7) C1 0.0378(12) 0.0380(12) 0.0341(12) 0.0029(9) 0.0028(9) -0.0025(9) C2 0.0427(12) 0.0375(12) 0.0322(12) 0.0006(10) 0.0001(9) -0.0045(9) C3 0.0433(12) 0.0231(10) 0.0402(12) -0.0019(9) 0.0014(10) -0.0016(8) C4 0.0374(11) 0.0326(11) 0.0378(12) 0.0064(10) -0.0020(9) -0.0041(9) C5 0.0376(11) 0.0332(11) 0.0301(11) 0.0020(9) 0.0028(9) -0.0017(9) C6 0.0376(11) 0.0242(10) 0.0316(11) 0.0008(8) 0.0039(9) 0.0005(8) C7 0.0383(11) 0.0241(10) 0.0294(11) 0.0018(8) 0.0028(9) -0.0006(8) C8 0.0381(11) 0.0244(10) 0.0329(11) 0.0023(8) 0.0040(9) 0.0003(8) C9 0.0406(12) 0.0300(11) 0.0325(11) -0.0021(9) 0.0034(9) -0.0001(9) C10 0.0547(14) 0.0350(12) 0.0470(14) -0.0049(10) 0.0099(11) -0.0002(10) C11 0.064(2) 0.0477(15) 0.057(2) -0.0119(12) 0.0222(13) 0.0021(12) C12 0.057(2) 0.061(2) 0.0415(14) -0.0055(12) 0.0181(12) -0.0059(12) C13 0.0524(13) 0.0386(12) 0.0408(13) 0.0037(10) 0.0089(11) -0.0038(10) C14 0.0385(11) 0.0310(11) 0.0314(11) -0.0024(9) 0.0019(9) -0.0011(9) C15 0.0447(13) 0.0474(15) 0.0379(13) 0.0079(11) 0.0033(10) 0.0017(10) C16 0.070(2) 0.083(2) 0.082(2) -0.003(2) -0.034(2) 0.009(2) C17 0.057(2) 0.052(2) 0.071(2) 0.0045(14) 0.0259(14) 0.0122(12) C18 0.073(2) 0.061(2) 0.0348(14) 0.0131(12) 0.0024(12) -0.0094(13) C19 0.0410(12) 0.0305(11) 0.0419(13) 0.0067(9) 0.0029(10) 0.0027(9) C20 0.0453(13) 0.0363(12) 0.0372(12) -0.0002(10) 0.0031(10) -0.0024(10) C21 0.0393(14) 0.077(2) 0.095(2) 0.008(2) -0.0091(14) -0.0087(13) C22 0.049(2) 0.115(3) 0.128(3) 0.026(3) -0.016(2) 0.012(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 O1 C4 1.207(2) . ? O2 C15 1.208(3) . ? O3 C5 1.388(3) . ? O3 C17 1.440(3) . ? O4 C5 1.420(2) . ? O4 C18 1.445(3) . ? O5 C20 1.191(3) . ? O6 C20 1.341(3) . ? O6 C21 1.446(3) . ? N1 C14 1.383(3) . ? N1 C7 1.466(3) . ? C1 C2 1.324(3) . ? C1 C15 1.483(3) . ? C1 C6 1.512(3) . ? C2 C3 1.503(3) . ? C3 C4 1.526(3) . ? C3 C8 1.560(3) . ? C4 C5 1.547(3) . ? C5 C6 1.542(3) . ? C6 C7 1.540(3) . ? C7 C8 1.557(3) . ? C8 C9 1.518(3) . ? C8 C19 1.531(3) . ? C9 C10 1.368(3) . ? C9 C14 1.394(3) . ? C10 C11 1.395(3) . ? C11 C12 1.377(4) . ? C12 C13 1.386(3) . ? C13 C14 1.388(3) . ? C15 C16 1.502(4) . ? C19 C20 1.495(3) . ? C21 C22 1.484(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 C5 O3 C17 115.2(2) . . ? C5 O4 C18 115.5(2) . . ? C20 O6 C21 117.1(2) . . ? C14 N1 C7 109.9(2) . . ? C2 C1 C15 124.8(2) . . ? C2 C1 C6 114.1(2) . . ? C15 C1 C6 121.0(2) . . ? C1 C2 C3 115.0(2) . . ? C2 C3 C4 101.7(2) . . ? C2 C3 C8 111.1(2) . . ? C4 C3 C8 108.9(2) . . ? O1 C4 C3 123.8(2) . . ? O1 C4 C5 123.9(2) . . ? C3 C4 C5 112.3(2) . . ? O3 C5 O4 112.2(2) . . ? O3 C5 C6 113.9(2) . . ? O4 C5 C6 107.2(2) . . ? O3 C5 C4 107.1(2) . . ? O4 C5 C4 109.4(2) . . ? C6 C5 C4 106.8(2) . . ? C1 C6 C7 109.3(2) . . ? C1 C6 C5 105.5(2) . . ? C7 C6 C5 109.3(2) . . ? N1 C7 C6 111.2(2) . . ? N1 C7 C8 105.6(2) . . ? C6 C7 C8 110.2(2) . . ? C9 C8 C19 111.5(2) . . ? C9 C8 C7 102.8(2) . . ? C19 C8 C7 114.7(2) . . ? C9 C8 C3 113.0(2) . . ? C19 C8 C3 106.7(2) . . ? C7 C8 C3 108.1(2) . . ? C10 C9 C14 121.0(2) . . ? C10 C9 C8 129.5(2) . . ? C14 C9 C8 109.3(2) . . ? C9 C10 C11 119.1(2) . . ? C12 C11 C10 119.9(2) . . ? C11 C12 C13 121.4(2) . . ? C14 C13 C12 118.4(2) . . ? N1 C14 C13 128.3(2) . . ? N1 C14 C9 111.5(2) . . ? C13 C14 C9 120.2(2) . . ? O2 C15 C1 120.2(2) . . ? O2 C15 C16 120.8(2) . . ? C1 C15 C16 118.9(2) . . ? C20 C19 C8 116.7(2) . . ? O5 C20 O6 124.0(2) . . ? O5 C20 C19 126.9(2) . . ? O6 C20 C19 109.1(2) . . ? O6 C21 C22 107.0(2) . . ? _refine_diff_density_max 0.402 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.041 data_ot17m _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 H14 Br N O4' _chemical_formula_weight 376.20 _chemical_melting_point ? _chemical_compound_source ? 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0176(2) _cell_length_b 9.4144(2) _cell_length_c 10.36370(10) _cell_angle_alpha 90.7060(10) _cell_angle_beta 96.9180(10) _cell_angle_gamma 117.1930(10) _cell_volume 774.62(2) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 5457 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Columnar _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 2.673 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6580 _exptl_absorpt_correction_T_max 0.9420 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens Smart CCD' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7349 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.92 _reflns_number_total 3317 _reflns_number_observed 2952 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Smart (Siemens, 1995)' _computing_cell_refinement 'Smart (Siemens, 1995)' _computing_data_reduction 'Smart (Siemens, 1995)' _computing_structure_solution 'SHELXTL-PLUS (Siemens, 1994)' _computing_structure_refinement 'SHELXTL-PLUS (Siemens, 1994)' _computing_molecular_graphics 'SHELXTL-PLUS (Siemens, 1994)' _computing_publication_material 'SHELXTL-PLUS (Siemens, 1994)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0364P)^2^+0.4249P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef ? _refine_ls_number_reflns 3316 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_obs 0.0349 _refine_ls_wR_factor_all 0.0957 _refine_ls_wR_factor_obs 0.0893 _refine_ls_goodness_of_fit_all 1.185 _refine_ls_goodness_of_fit_obs 1.178 _refine_ls_restrained_S_all 1.187 _refine_ls_restrained_S_obs 1.178 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Br1 Br 0.28502(4) 0.15066(4) 0.48139(3) 0.06226(13) Uani 1 d . . O1 O -0.2615(2) 0.2353(2) 0.5572(2) 0.0447(4) Uani 1 d . . O2 O -0.1070(3) 0.4465(2) 0.7005(2) 0.0484(4) Uani 1 d . . O3 O -0.0502(2) 0.0931(2) 1.0837(2) 0.0374(4) Uani 1 d . . O4 O -0.3652(2) -0.1605(2) 1.0448(2) 0.0459(4) Uani 1 d . . N1 N 0.3191(2) 0.5408(2) 0.9558(2) 0.0367(4) Uani 1 d . . C1 C 0.1776(2) 0.3382(2) 0.8008(2) 0.0285(4) Uani 1 d . . C2 C 0.1602(3) 0.2422(3) 0.6899(2) 0.0337(5) Uani 1 d . . C3 C 0.3000(3) 0.2836(3) 0.6276(2) 0.0382(5) Uani 1 d . . C4 C 0.4556(3) 0.4182(3) 0.6698(3) 0.0419(5) Uani 1 d . . C5 C 0.4743(3) 0.5145(3) 0.7779(2) 0.0386(5) Uani 1 d . . C6 C 0.3351(3) 0.4735(2) 0.8436(2) 0.0316(4) Uani 1 d . . C7 C 0.1599(3) 0.4515(3) 0.9874(2) 0.0341(5) Uani 1 d . . C8 C 0.0675(2) 0.3274(2) 0.8945(2) 0.0285(4) Uani 1 d . . C9 C -0.1106(2) 0.2018(2) 0.8850(2) 0.0275(4) Uani 1 d . . C10 C -0.1602(3) 0.0874(2) 0.9771(2) 0.0290(4) Uani 1 d . . C11 C -0.3207(3) -0.0442(2) 0.9584(2) 0.0326(4) Uani 1 d . . C12 C -0.4367(3) -0.0603(3) 0.8517(2) 0.0373(5) Uani 1 d . . C13 C -0.3913(3) 0.0529(3) 0.7606(2) 0.0354(5) Uani 1 d . . C14 C -0.2300(3) 0.1829(2) 0.7758(2) 0.0298(4) Uani 1 d . . C15 C -0.1895(3) 0.3046(3) 0.6773(2) 0.0307(4) Uani 1 d . . C16 C -0.2357(4) 0.3402(4) 0.4527(3) 0.0547(7) Uani 1 d . . C17 C -0.0626(4) 0.1706(4) 1.1998(3) 0.0560(7) Uani 1 d . . H1 H 0.3994 0.6178 1.0018 0.080 Uiso 1 d . . H4 H -0.2838 -0.1501 1.0924 0.080 Uiso 1 d . . H2A H 0.0583 0.1520 0.6577 0.080 Uiso 1 d . . H4A H 0.5471 0.4428 0.6268 0.080 Uiso 1 d . . H5A H 0.5805 0.6077 0.8064 0.080 Uiso 1 d . . H7A H 0.1300 0.4865 1.0610 0.080 Uiso 1 d . . H12A H -0.5482 -0.1490 0.8431 0.080 Uiso 1 d . . H13A H -0.4691 0.0409 0.6836 0.080 Uiso 1 d . . H16A H -0.2379 0.4389 0.4798 0.080 Uiso 1 d . . H16B H -0.3217 0.2807 0.3841 0.080 Uiso 1 d . . H16C H -0.1306 0.3665 0.4301 0.080 Uiso 1 d . . H17A H -0.0692 0.2714 1.1815 0.080 Uiso 1 d . . H17B H 0.0233 0.1826 1.2645 0.080 Uiso 1 d . . H17C H -0.1776 0.0928 1.2321 0.080 Uiso 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 Br1 0.0518(2) 0.0736(2) 0.0573(2) -0.01822(15) 0.01118(13) 0.0253(2) O1 0.0489(10) 0.0394(9) 0.0304(8) 0.0033(7) -0.0017(7) 0.0089(8) O2 0.0617(12) 0.0289(8) 0.0394(9) 0.0049(7) 0.0034(8) 0.0086(8) O3 0.0323(8) 0.0374(8) 0.0359(8) 0.0018(6) -0.0069(6) 0.0132(7) O4 0.0356(9) 0.0330(8) 0.0516(10) 0.0165(7) -0.0049(7) 0.0031(7) N1 0.0271(9) 0.0282(9) 0.0388(10) -0.0028(7) -0.0024(7) 0.0010(7) C1 0.0225(9) 0.0253(9) 0.0324(10) 0.0045(8) 0.0006(8) 0.0071(8) C2 0.0266(10) 0.0326(10) 0.0369(11) 0.0002(9) 0.0010(8) 0.0103(8) C3 0.0351(11) 0.0415(12) 0.0383(12) 0.0015(9) 0.0050(9) 0.0179(10) C4 0.0298(11) 0.0478(13) 0.0467(13) 0.0119(11) 0.0110(10) 0.0152(10) C5 0.0242(10) 0.0357(11) 0.0465(13) 0.0090(10) 0.0036(9) 0.0060(9) C6 0.0232(9) 0.0267(10) 0.0358(11) 0.0056(8) 0.0003(8) 0.0047(8) C7 0.0292(10) 0.0307(10) 0.0335(11) 0.0002(8) 0.0000(8) 0.0074(8) C8 0.0225(9) 0.0247(9) 0.0318(10) 0.0016(8) 0.0005(8) 0.0062(8) C9 0.0227(9) 0.0251(9) 0.0301(10) -0.0024(8) 0.0015(7) 0.0079(8) C10 0.0249(9) 0.0273(10) 0.0312(10) -0.0007(8) -0.0004(8) 0.0099(8) C11 0.0296(10) 0.0255(10) 0.0369(11) 0.0046(8) 0.0023(8) 0.0084(8) C12 0.0246(10) 0.0302(10) 0.0439(12) 0.0040(9) -0.0020(9) 0.0029(8) C13 0.0255(10) 0.0335(11) 0.0367(11) 0.0018(9) -0.0032(8) 0.0065(9) C14 0.0256(10) 0.0286(10) 0.0304(10) 0.0011(8) 0.0016(8) 0.0088(8) C15 0.0289(10) 0.0321(10) 0.0294(10) 0.0028(8) 0.0030(8) 0.0129(8) C16 0.057(2) 0.061(2) 0.0322(12) 0.0113(12) 0.0022(11) 0.0161(14) C17 0.068(2) 0.051(2) 0.0360(13) -0.0047(11) -0.0073(12) 0.0191(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 Br1 C3 1.905(2) . ? O1 C15 1.340(3) . ? O1 C16 1.442(3) . ? O2 C15 1.199(3) . ? O3 C10 1.376(2) . ? O3 C17 1.442(3) . ? O4 C11 1.367(3) . ? N1 C6 1.371(3) . ? N1 C7 1.376(3) . ? C1 C2 1.402(3) . ? C1 C6 1.421(3) . ? C1 C8 1.443(3) . ? C2 C3 1.382(3) . ? C3 C4 1.407(3) . ? C4 C5 1.377(4) . ? C5 C6 1.399(3) . ? C7 C8 1.369(3) . ? C8 C9 1.486(3) . ? C9 C10 1.400(3) . ? C9 C14 1.414(3) . ? C10 C11 1.398(3) . ? C11 C12 1.383(3) . ? C12 C13 1.383(3) . ? C13 C14 1.396(3) . ? C14 C15 1.492(3) . ? 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 C15 O1 C16 116.8(2) . . ? C10 O3 C17 113.5(2) . . ? C6 N1 C7 109.6(2) . . ? C2 C1 C6 119.4(2) . . ? C2 C1 C8 133.7(2) . . ? C6 C1 C8 106.8(2) . . ? C3 C2 C1 117.7(2) . . ? C2 C3 C4 122.8(2) . . ? C2 C3 Br1 119.1(2) . . ? C4 C3 Br1 118.1(2) . . ? C5 C4 C3 120.2(2) . . ? C4 C5 C6 118.0(2) . . ? N1 C6 C5 130.8(2) . . ? N1 C6 C1 107.3(2) . . ? C5 C6 C1 121.9(2) . . ? C8 C7 N1 109.8(2) . . ? C7 C8 C1 106.6(2) . . ? C7 C8 C9 129.5(2) . . ? C1 C8 C9 123.9(2) . . ? C10 C9 C14 117.8(2) . . ? C10 C9 C8 120.6(2) . . ? C14 C9 C8 121.3(2) . . ? O3 C10 C11 117.4(2) . . ? O3 C10 C9 121.7(2) . . ? C11 C10 C9 120.7(2) . . ? O4 C11 C12 118.7(2) . . ? O4 C11 C10 120.5(2) . . ? C12 C11 C10 120.8(2) . . ? C11 C12 C13 119.4(2) . . ? C12 C13 C14 120.6(2) . . ? C13 C14 C9 120.6(2) . . ? C13 C14 C15 118.4(2) . . ? C9 C14 C15 120.9(2) . . ? O2 C15 O1 123.4(2) . . ? O2 C15 C14 125.5(2) . . ? O1 C15 C14 111.1(2) . . ? _refine_diff_density_max 0.450 _refine_diff_density_min -0.692 _refine_diff_density_rms 0.053