# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Gabriele Kociok-Kohn' _publ_contact_author_email chsgk@bath.ac.uk loop_ _publ_author_name J.A.Griffen A.M.L.Coz G.Kociok-Kohn M.A.Khan A.J.W.Stewart ; S.E.Lewis ; # Attachment 'Compound-21.cif' data_h10sel3 _database_code_depnum_ccdc_archive 'CCDC 808269' #TrackingRef 'Compound-21.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H13 Br Fe O7' _chemical_formula_sum 'C14 H13 Br Fe O7' _chemical_formula_weight 429.00 _chemical_absolute_configuration ad 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' 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.6252(3) _cell_length_b 8.6773(3) _cell_length_c 43.7286(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3272.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 52435 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.741 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 3.394 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3104 _exptl_absorpt_correction_T_max 0.6300 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD' _diffrn_measurement_method '1240 0.8 degree images with \f and \w scans' _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 25844 _diffrn_reflns_av_R_equivalents 0.0663 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -56 _diffrn_reflns_limit_l_max 56 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 27.56 _reflns_number_total 6937 _reflns_number_gt 5544 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinski & Minor, 1997)' _computing_data_reduction ; DENZO-SCALEPACK Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press. ; _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. (1999) J. Appl. Cryst. 32, 115-119 ; _computing_structure_refinement ; SHELXL97 -Program for Crystal Structure Analysis (Release 97-2). Sheldrick, G.M., Institut f\"ur Anorganische Chemie der Universit\"at, Tammanstrasse 4, D-3400 G\"ottingen, Germany, 1998 ; _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material ; 'WinGX publication routines, Farrugia, L. J., J. Appl. Crystallogr., 1999, 32, 837-838 ; _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^)+(0.0281P)^2^+3.0101P] 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 0.011(9) _refine_ls_number_reflns 6937 _refine_ls_number_parameters 429 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.0860 _refine_ls_wR_factor_gt 0.0788 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 Fe1 Fe 1.06298(7) 0.30036(8) 0.178918(14) 0.02869(16) Uani 1 1 d . . . C10 C 1.1952(6) 0.4506(7) 0.16908(11) 0.0374(12) Uani 1 1 d . . . O10 O 1.2725(4) 0.5543(5) 0.16372(10) 0.0550(11) Uani 1 1 d . . . C20 C 0.9414(5) 0.3129(5) 0.14597(11) 0.0331(11) Uani 1 1 d . . . O20 O 0.8621(4) 0.3203(5) 0.12515(7) 0.0477(9) Uani 1 1 d . . . C30 C 1.1935(7) 0.1555(7) 0.16563(12) 0.0488(14) Uani 1 1 d . . . O30 O 1.2798(6) 0.0659(6) 0.15641(11) 0.0818(16) Uani 1 1 d . . . Br1 Br 0.90920(6) -0.06311(6) 0.194481(12) 0.04028(14) Uani 1 1 d . . . O1 O 0.5849(4) 0.4037(4) 0.16607(9) 0.0453(10) Uani 1 1 d . . . O2 O 0.7164(4) 0.6167(4) 0.17670(8) 0.0335(8) Uani 1 1 d . . . O3 O 0.6991(3) 0.4460(4) 0.23537(7) 0.0259(7) Uani 1 1 d . . . O4 O 0.7042(3) 0.1862(4) 0.23717(7) 0.0315(7) Uani 1 1 d . . . C1 C 0.7613(5) 0.2229(5) 0.20752(11) 0.0246(10) Uani 1 1 d . . . H1 H 0.6883 0.1862 0.1913 0.030 Uiso 1 1 calc R . . C2 C 0.9181(5) 0.1552(5) 0.20314(9) 0.0280(10) Uani 1 1 d . . . C3 C 1.0416(5) 0.2056(5) 0.22176(9) 0.0271(10) Uani 1 1 d . . . H3 H 1.1108 0.1375 0.2319 0.033 Uiso 1 1 calc R . . C4 C 1.0515(5) 0.3662(5) 0.22374(10) 0.0272(10) Uani 1 1 d . . . H4 H 1.1291 0.4164 0.2355 0.033 Uiso 1 1 calc R . . C5 C 0.9388(5) 0.4487(6) 0.20709(10) 0.0257(10) Uani 1 1 d . . . C6 C 0.7726(5) 0.4003(5) 0.20745(10) 0.0242(10) Uani 1 1 d . . . C7 C 0.6801(5) 0.4696(5) 0.18089(10) 0.0269(10) Uani 1 1 d . . . C8 C 0.6394(5) 0.6928(6) 0.15137(12) 0.0387(12) Uani 1 1 d . . . H8A H 0.6639 0.6388 0.1323 0.058 Uiso 1 1 calc R . . H8B H 0.6753 0.7998 0.1500 0.058 Uiso 1 1 calc R . . H8C H 0.5271 0.6914 0.1547 0.058 Uiso 1 1 calc R . . C9 C 0.6190(5) 0.3148(5) 0.24814(11) 0.0292(10) Uani 1 1 d . . . C11 C 0.6334(6) 0.3219(7) 0.28229(12) 0.0432(13) Uani 1 1 d . . . H11A H 0.5835 0.2313 0.2913 0.065 Uiso 1 1 calc R . . H11B H 0.5829 0.4155 0.2899 0.065 Uiso 1 1 calc R . . H11C H 0.7433 0.3234 0.2880 0.065 Uiso 1 1 calc R . . C12 C 0.4525(5) 0.3111(6) 0.23757(12) 0.0404(12) Uani 1 1 d . . . H12A H 0.4493 0.2989 0.2153 0.061 Uiso 1 1 calc R . . H12B H 0.4012 0.4078 0.2433 0.061 Uiso 1 1 calc R . . H12C H 0.3988 0.2244 0.2473 0.061 Uiso 1 1 calc R . . Fe2 Fe 1.05368(8) 0.82356(7) 0.070867(14) 0.03102(16) Uani 1 1 d . . . C40 C 1.2113(8) 0.9453(7) 0.08140(12) 0.0487(14) Uani 1 1 d . . . C50 C 1.0325(5) 0.7159(6) 0.10578(11) 0.0338(12) Uani 1 1 d . . . C60 C 0.9096(8) 0.9641(7) 0.08035(12) 0.0524(16) Uani 1 1 d . . . O40 O 1.3210(6) 1.0130(5) 0.08811(11) 0.0796(16) Uani 1 1 d . . . O50 O 1.0073(5) 0.6542(4) 0.12786(9) 0.0535(10) Uani 1 1 d . . . O60 O 0.8167(6) 1.0514(6) 0.08690(11) 0.0855(16) Uani 1 1 d . . . Br2 Br 0.68912(6) 0.67190(6) 0.054416(11) 0.03870(13) Uani 1 1 d . . . O5 O 1.1603(4) 0.3692(5) 0.09038(10) 0.0588(13) Uani 1 1 d . . . O6 O 1.3814(4) 0.4496(4) 0.07063(8) 0.0355(8) Uani 1 1 d . . . O7 O 1.1983(3) 0.4543(4) 0.01631(7) 0.0268(7) Uani 1 1 d . . . O8 O 0.9357(4) 0.4498(4) 0.01650(7) 0.0336(8) Uani 1 1 d . . . C21 C 0.9769(5) 0.5174(5) 0.04508(11) 0.0274(11) Uani 1 1 d . . . H21 H 0.9404 0.4523 0.0625 0.033 Uiso 1 1 calc R . . C22 C 0.9099(5) 0.6770(5) 0.04695(10) 0.0287(10) Uani 1 1 d . . . C23 C 0.9665(5) 0.7941(5) 0.02784(10) 0.0293(11) Uani 1 1 d . . . H23 H 0.9008 0.8622 0.0168 0.035 Uiso 1 1 calc R . . C24 C 1.1290(6) 0.8018(5) 0.02646(10) 0.0317(11) Uani 1 1 d . . . H24 H 1.1823 0.8752 0.0142 0.038 Uiso 1 1 calc R . . C25 C 1.2078(6) 0.6912(6) 0.04475(11) 0.0286(10) Uani 1 1 d . . . C26 C 1.1539(5) 0.5273(5) 0.04457(10) 0.0242(10) Uani 1 1 d . . . C27 C 1.2292(5) 0.4390(5) 0.07149(10) 0.0251(10) Uani 1 1 d . . . C28 C 1.4656(6) 0.3757(6) 0.09522(12) 0.0365(12) Uani 1 1 d . . . H28A H 1.4395 0.4257 0.1147 0.055 Uiso 1 1 calc R . . H28B H 1.5772 0.3849 0.0915 0.055 Uiso 1 1 calc R . . H28C H 1.4370 0.2665 0.0962 0.055 Uiso 1 1 calc R . . C29 C 1.0673(5) 0.3691(5) 0.00529(11) 0.0289(10) Uani 1 1 d . . . C31 C 1.0679(7) 0.3765(6) -0.02897(12) 0.0472(14) Uani 1 1 d . . . H31A H 0.9735 0.3281 -0.0369 0.071 Uiso 1 1 calc R . . H31B H 1.1589 0.3218 -0.0369 0.071 Uiso 1 1 calc R . . H31C H 1.0717 0.4844 -0.0355 0.071 Uiso 1 1 calc R . . C32 C 1.0713(6) 0.2062(5) 0.01736(13) 0.0438(13) Uani 1 1 d . . . H32A H 1.0663 0.2080 0.0397 0.066 Uiso 1 1 calc R . . H32B H 1.1676 0.1561 0.0109 0.066 Uiso 1 1 calc R . . H32C H 0.9824 0.1487 0.0093 0.066 Uiso 1 1 calc R . . H25 H 1.314(5) 0.705(5) 0.0436(9) 0.017(10) Uiso 1 1 d . . . H5 H 0.948(4) 0.546(5) 0.2082(9) 0.013(11) 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 Fe1 0.0295(3) 0.0364(4) 0.0202(3) -0.0006(3) 0.0008(3) 0.0029(3) C10 0.029(3) 0.052(3) 0.032(3) -0.006(3) -0.004(2) 0.002(3) O10 0.037(2) 0.068(3) 0.059(3) 0.003(2) 0.0029(19) -0.020(2) C20 0.037(3) 0.030(3) 0.032(3) -0.005(2) 0.011(2) -0.006(3) O20 0.048(2) 0.076(3) 0.0191(17) 0.0000(19) -0.0083(15) -0.013(2) C30 0.058(3) 0.061(4) 0.027(3) 0.006(3) 0.015(3) 0.019(3) O30 0.109(4) 0.078(3) 0.058(3) 0.013(3) 0.042(3) 0.052(3) Br1 0.0590(3) 0.0281(3) 0.0337(3) -0.0032(2) -0.0049(3) 0.0073(3) O1 0.046(2) 0.037(2) 0.053(2) 0.0034(17) -0.0301(19) -0.0070(18) O2 0.0373(18) 0.0304(19) 0.0328(19) 0.0094(14) -0.0099(16) -0.0092(15) O3 0.0245(15) 0.0284(17) 0.0248(16) 0.0004(14) 0.0032(14) -0.0008(16) O4 0.0310(16) 0.0280(17) 0.0354(18) 0.0061(15) 0.0067(15) 0.0020(17) C1 0.024(2) 0.026(3) 0.023(2) 0.0021(19) -0.0016(18) -0.0015(19) C2 0.040(3) 0.026(2) 0.018(2) -0.0014(18) -0.002(2) 0.000(2) C3 0.030(2) 0.037(3) 0.015(2) 0.0020(19) 0.0027(18) 0.007(2) C4 0.026(2) 0.038(3) 0.018(2) -0.0046(18) -0.0030(19) -0.002(2) C5 0.024(2) 0.029(3) 0.024(2) -0.004(2) 0.001(2) -0.008(2) C6 0.022(2) 0.031(3) 0.019(2) 0.0014(19) -0.0026(18) 0.0006(19) C7 0.028(2) 0.029(3) 0.024(2) 0.0001(19) -0.001(2) -0.001(2) C8 0.042(3) 0.034(3) 0.040(3) 0.013(2) -0.011(2) -0.006(2) C9 0.026(2) 0.028(3) 0.033(2) 0.001(2) 0.005(2) -0.001(2) C11 0.039(3) 0.056(3) 0.034(3) 0.006(3) 0.009(2) 0.002(3) C12 0.028(3) 0.040(3) 0.053(3) 0.004(3) 0.002(2) -0.006(3) Fe2 0.0479(4) 0.0241(3) 0.0210(3) 0.0001(3) -0.0011(3) 0.0008(4) C40 0.082(4) 0.032(3) 0.032(3) 0.002(3) 0.008(3) -0.009(4) C50 0.040(3) 0.035(3) 0.027(3) 0.001(2) 0.001(2) 0.003(2) C60 0.079(4) 0.046(4) 0.033(3) -0.008(3) -0.019(3) 0.011(4) O40 0.101(4) 0.079(4) 0.058(3) -0.020(2) 0.006(3) -0.054(3) O50 0.072(3) 0.053(3) 0.036(2) 0.0163(19) 0.0069(19) -0.002(2) O60 0.108(4) 0.073(3) 0.076(4) -0.033(3) -0.025(3) 0.054(3) Br2 0.0336(2) 0.0498(3) 0.0327(3) 0.0043(3) 0.0024(2) 0.0110(3) O5 0.034(2) 0.084(3) 0.059(3) 0.046(2) 0.0070(19) 0.004(2) O6 0.0340(19) 0.0393(19) 0.0332(19) 0.0089(17) -0.0102(15) -0.0012(17) O7 0.0287(16) 0.0296(17) 0.0222(16) -0.0007(14) 0.0026(14) -0.0032(15) O8 0.0332(18) 0.0289(17) 0.0388(19) -0.0102(15) -0.0075(16) 0.0001(17) C21 0.033(3) 0.020(2) 0.029(3) 0.0011(19) 0.002(2) 0.002(2) C22 0.032(2) 0.032(2) 0.022(2) -0.002(2) -0.0008(19) 0.003(2) C23 0.037(3) 0.030(3) 0.021(2) -0.001(2) -0.0014(19) 0.009(2) C24 0.052(3) 0.020(2) 0.023(2) 0.002(2) 0.005(2) -0.004(2) C25 0.028(2) 0.025(3) 0.032(2) 0.002(2) 0.003(2) -0.003(2) C26 0.027(3) 0.023(3) 0.023(2) -0.0003(18) 0.0026(19) 0.0000(19) C27 0.028(3) 0.026(2) 0.022(2) 0.001(2) -0.0018(19) 0.002(2) C28 0.039(3) 0.037(3) 0.034(3) 0.002(2) -0.019(2) 0.000(2) C29 0.030(2) 0.026(2) 0.030(3) -0.0032(19) -0.002(2) -0.002(2) C31 0.057(3) 0.051(3) 0.034(3) -0.006(2) -0.011(3) -0.011(3) C32 0.044(3) 0.021(2) 0.067(4) -0.003(2) 0.005(3) 0.000(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 Fe1 C30 1.785(6) . ? Fe1 C10 1.785(6) . ? Fe1 C20 1.785(5) . ? Fe1 C4 2.044(4) . ? Fe1 C3 2.054(4) . ? Fe1 C2 2.066(5) . ? Fe1 C5 2.079(5) . ? C10 O10 1.143(6) . ? C20 O20 1.141(5) . ? C30 O30 1.149(6) . ? Br1 C2 1.933(4) . ? O1 C7 1.193(5) . ? O2 C7 1.326(5) . ? O2 C8 1.451(5) . ? O3 C6 1.432(5) . ? O3 C9 1.444(5) . ? O4 C9 1.420(5) . ? O4 C1 1.423(5) . ? C1 C2 1.487(6) . ? C1 C6 1.543(6) . ? C1 H1 1.0000 . ? C2 C3 1.410(6) . ? C3 C4 1.399(6) . ? C3 H3 0.9500 . ? C4 C5 1.410(6) . ? C4 H4 0.9500 . ? C5 C6 1.494(6) . ? C5 H5 0.85(4) . ? C6 C7 1.532(6) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C11 1.500(6) . ? C9 C12 1.509(6) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? Fe2 C40 1.782(7) . ? Fe2 C60 1.790(6) . ? Fe2 C50 1.799(5) . ? Fe2 C23 2.042(4) . ? Fe2 C24 2.057(5) . ? Fe2 C22 2.061(4) . ? Fe2 C25 2.096(5) . ? C40 O40 1.151(7) . ? C50 O50 1.125(5) . ? C60 O60 1.139(7) . ? Br2 C22 1.933(4) . ? O5 C27 1.184(5) . ? O6 C27 1.317(5) . ? O6 C28 1.447(5) . ? O7 C29 1.433(5) . ? O7 C26 1.441(5) . ? O8 C29 1.421(5) . ? O8 C21 1.426(5) . ? C21 C22 1.503(6) . ? C21 C26 1.528(6) . ? C21 H21 1.0000 . ? C22 C23 1.404(6) . ? C23 C24 1.405(7) . ? C23 H23 0.9500 . ? C24 C25 1.422(7) . ? C24 H24 0.9500 . ? C25 C26 1.496(7) . ? C25 H25 0.93(4) . ? C26 C27 1.547(6) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C31 1.500(6) . ? C29 C32 1.509(6) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 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 C30 Fe1 C10 91.9(2) . . ? C30 Fe1 C20 98.7(2) . . ? C10 Fe1 C20 97.8(2) . . ? C30 Fe1 C4 122.7(2) . . ? C10 Fe1 C4 93.3(2) . . ? C20 Fe1 C4 136.7(2) . . ? C30 Fe1 C3 94.1(2) . . ? C10 Fe1 C3 124.7(2) . . ? C20 Fe1 C3 135.03(19) . . ? C4 Fe1 C3 39.93(17) . . ? C30 Fe1 C2 96.8(2) . . ? C10 Fe1 C2 162.8(2) . . ? C20 Fe1 C2 95.5(2) . . ? C4 Fe1 C2 69.49(17) . . ? C3 Fe1 C2 40.01(17) . . ? C30 Fe1 C5 162.6(2) . . ? C10 Fe1 C5 91.1(2) . . ? C20 Fe1 C5 97.92(19) . . ? C4 Fe1 C5 39.97(17) . . ? C3 Fe1 C5 70.20(18) . . ? C2 Fe1 C5 76.24(18) . . ? O10 C10 Fe1 175.0(5) . . ? O20 C20 Fe1 179.1(4) . . ? O30 C30 Fe1 177.6(5) . . ? C7 O2 C8 115.8(4) . . ? C6 O3 C9 108.9(3) . . ? C9 O4 C1 108.1(3) . . ? O4 C1 C2 110.1(3) . . ? O4 C1 C6 104.3(4) . . ? C2 C1 C6 109.7(4) . . ? O4 C1 H1 110.9 . . ? C2 C1 H1 110.9 . . ? C6 C1 H1 110.9 . . ? C3 C2 C1 119.4(4) . . ? C3 C2 Br1 116.6(3) . . ? C1 C2 Br1 112.1(3) . . ? C3 C2 Fe1 69.5(3) . . ? C1 C2 Fe1 112.0(3) . . ? Br1 C2 Fe1 121.4(2) . . ? C4 C3 C2 113.0(4) . . ? C4 C3 Fe1 69.6(3) . . ? C2 C3 Fe1 70.4(3) . . ? C4 C3 H3 123.5 . . ? C2 C3 H3 123.5 . . ? Fe1 C3 H3 128.2 . . ? C3 C4 C5 115.6(4) . . ? C3 C4 Fe1 70.4(3) . . ? C5 C4 Fe1 71.4(3) . . ? C3 C4 H4 122.2 . . ? C5 C4 H4 122.2 . . ? Fe1 C4 H4 127.9 . . ? C4 C5 C6 120.9(4) . . ? C4 C5 Fe1 68.7(3) . . ? C6 C5 Fe1 109.1(3) . . ? C4 C5 H5 114(3) . . ? C6 C5 H5 112(3) . . ? Fe1 C5 H5 127(3) . . ? O3 C6 C5 110.9(3) . . ? O3 C6 C7 107.9(3) . . ? C5 C6 C7 112.4(4) . . ? O3 C6 C1 104.3(4) . . ? C5 C6 C1 109.9(4) . . ? C7 C6 C1 111.1(4) . . ? O1 C7 O2 123.3(4) . . ? O1 C7 C6 125.6(4) . . ? O2 C7 C6 111.1(4) . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O4 C9 O3 104.0(3) . . ? O4 C9 C11 109.0(4) . . ? O3 C9 C11 108.3(4) . . ? O4 C9 C12 111.9(4) . . ? O3 C9 C12 110.7(4) . . ? C11 C9 C12 112.6(4) . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C40 Fe2 C60 93.8(3) . . ? C40 Fe2 C50 99.6(2) . . ? C60 Fe2 C50 95.0(2) . . ? C40 Fe2 C23 126.4(2) . . ? C60 Fe2 C23 92.5(2) . . ? C50 Fe2 C23 132.8(2) . . ? C40 Fe2 C24 93.3(2) . . ? C60 Fe2 C24 120.1(2) . . ? C50 Fe2 C24 141.8(2) . . ? C23 Fe2 C24 40.08(18) . . ? C40 Fe2 C22 162.9(2) . . ? C60 Fe2 C22 96.9(2) . . ? C50 Fe2 C22 92.8(2) . . ? C23 Fe2 C22 40.00(18) . . ? C24 Fe2 C22 69.78(18) . . ? C40 Fe2 C25 88.9(2) . . ? C60 Fe2 C25 160.1(2) . . ? C50 Fe2 C25 104.0(2) . . ? C23 Fe2 C25 70.30(18) . . ? C24 Fe2 C25 40.04(18) . . ? C22 Fe2 C25 76.53(17) . . ? O40 C40 Fe2 174.2(6) . . ? O50 C50 Fe2 174.2(4) . . ? O60 C60 Fe2 178.4(6) . . ? C27 O6 C28 116.6(4) . . ? C29 O7 C26 107.8(3) . . ? C29 O8 C21 107.8(3) . . ? O8 C21 C22 109.3(4) . . ? O8 C21 C26 105.1(4) . . ? C22 C21 C26 109.5(4) . . ? O8 C21 H21 110.9 . . ? C22 C21 H21 110.9 . . ? C26 C21 H21 110.9 . . ? C23 C22 C21 120.1(4) . . ? C23 C22 Br2 117.4(3) . . ? C21 C22 Br2 111.5(3) . . ? C23 C22 Fe2 69.3(3) . . ? C21 C22 Fe2 111.4(3) . . ? Br2 C22 Fe2 121.4(2) . . ? C22 C23 C24 114.0(4) . . ? C22 C23 Fe2 70.7(3) . . ? C24 C23 Fe2 70.5(3) . . ? C22 C23 H23 123.0 . . ? C24 C23 H23 123.0 . . ? Fe2 C23 H23 127.5 . . ? C23 C24 C25 114.9(4) . . ? C23 C24 Fe2 69.4(3) . . ? C25 C24 Fe2 71.5(3) . . ? C23 C24 H24 122.6 . . ? C25 C24 H24 122.6 . . ? Fe2 C24 H24 128.5 . . ? C24 C25 C26 119.3(4) . . ? C24 C25 Fe2 68.5(3) . . ? C26 C25 Fe2 109.0(3) . . ? C24 C25 H25 111(3) . . ? C26 C25 H25 115(3) . . ? Fe2 C25 H25 126(3) . . ? O7 C26 C25 109.8(3) . . ? O7 C26 C21 104.7(4) . . ? C25 C26 C21 111.4(4) . . ? O7 C26 C27 108.9(3) . . ? C25 C26 C27 109.6(4) . . ? C21 C26 C27 112.3(4) . . ? O5 C27 O6 123.8(4) . . ? O5 C27 C26 125.0(4) . . ? O6 C27 C26 111.2(4) . . ? O6 C28 H28A 109.5 . . ? O6 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O6 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O8 C29 O7 105.1(3) . . ? O8 C29 C31 109.0(4) . . ? O7 C29 C31 108.1(4) . . ? O8 C29 C32 111.0(4) . . ? O7 C29 C32 110.4(4) . . ? C31 C29 C32 112.9(4) . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.554 _refine_diff_density_min -0.567 _refine_diff_density_rms 0.086 data_p10sel1 _database_code_depnum_ccdc_archive 'CCDC 808270' #TrackingRef 'Compound-13.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H18 Br N3 O6' _chemical_formula_sum 'C19 H18 Br N3 O6' _chemical_formula_weight 464.27 _chemical_absolute_configuration ad 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 hexagonal _symmetry_space_group_name_H-M 'P 65' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x-y, z+2/3' 'y, -x+y, z+1/6' '-x+y, -x, z+1/3' 'x-y, x, z+5/6' _cell_length_a 27.8075(4) _cell_length_b 27.8075(4) _cell_length_c 6.47080(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4333.24(11) _cell_formula_units_Z 6 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 21306 _cell_measurement_theta_min 3.1759 _cell_measurement_theta_max 66.6305 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.067 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 2.196 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4737 _exptl_absorpt_correction_T_max 0.8103 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3795 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 52878 _diffrn_reflns_av_R_equivalents 0.0752 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 4.86 _diffrn_reflns_theta_max 66.74 _reflns_number_total 4920 _reflns_number_gt 4623 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _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. (1999) J. Appl. Cryst. 32, 115-119 ; _computing_structure_refinement ; SHELXL97 -Program for Crystal Structure Analysis (Release 97-2). Sheldrick, G.M., Instit\"ut f\"ur Anorganische Chemie der Universit\"at, Tammanstrasse 4, D-3400 G\"ottingen, Germany, 1998 ; _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material ; 'WinGX publication routines, Farrugia, L. J., J. Appl. Crystallogr., 1999, 32, 837-838 ; _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^)+(0.0409P)^2^+1.5171P] 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 ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 2124 Friedel pairs' _refine_ls_abs_structure_Flack -0.003(17) _refine_ls_number_reflns 4920 _refine_ls_number_parameters 265 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0864 _refine_ls_wR_factor_gt 0.0850 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.265573(15) 0.349617(14) 0.13960(6) 0.04269(10) Uani 1 1 d . . . N1 N 0.34432(10) 0.47629(11) 0.5658(4) 0.0315(5) Uani 1 1 d . . . N2 N 0.33632(10) 0.43423(10) 0.4164(4) 0.0309(5) Uani 1 1 d . . . N3 N 0.39406(10) 0.43838(10) 0.6624(4) 0.0324(6) Uani 1 1 d . . . O1 O 0.33534(11) 0.56463(10) 0.1551(5) 0.0518(6) Uani 1 1 d . . . O2 O 0.35046(11) 0.59006(10) 0.4867(5) 0.0579(7) Uani 1 1 d . . . O3 O 0.22962(8) 0.49598(9) 0.4150(4) 0.0385(5) Uani 1 1 d . . . O4 O 0.21536(9) 0.42932(10) 0.1759(4) 0.0413(5) Uani 1 1 d . . . O5 O 0.38995(10) 0.50362(11) 0.8774(4) 0.0482(6) Uani 1 1 d . . . O6 O 0.36798(9) 0.37029(9) 0.4114(4) 0.0392(5) Uani 1 1 d . . . C1 C 0.3764(2) 0.62087(17) 0.0931(9) 0.0782(15) Uani 1 1 d . . . H1A H 0.3660 0.6471 0.1488 0.117 Uiso 1 1 calc R . . H1B H 0.3780 0.6233 -0.0580 0.117 Uiso 1 1 calc R . . H1C H 0.4129 0.6299 0.1469 0.117 Uiso 1 1 calc R . . C2 C 0.32649(14) 0.55551(14) 0.3586(6) 0.0406(8) Uani 1 1 d . . . C3 C 0.28075(12) 0.49632(13) 0.4040(5) 0.0337(7) Uani 1 1 d . . . C4 C 0.19437(13) 0.46427(14) 0.2445(6) 0.0391(7) Uani 1 1 d . . . C5 C 0.19854(17) 0.50278(17) 0.0692(6) 0.0516(9) Uani 1 1 d . . . H5A H 0.2376 0.5267 0.0312 0.077 Uiso 1 1 calc R . . H5B H 0.1829 0.5258 0.1144 0.077 Uiso 1 1 calc R . . H5C H 0.1778 0.4806 -0.0507 0.077 Uiso 1 1 calc R . . C6 C 0.13684(14) 0.42923(17) 0.3254(8) 0.0570(10) Uani 1 1 d . . . H6A H 0.1372 0.4061 0.4391 0.086 Uiso 1 1 calc R . . H6B H 0.1127 0.4054 0.2145 0.086 Uiso 1 1 calc R . . H6C H 0.1228 0.4532 0.3757 0.086 Uiso 1 1 calc R . . C7 C 0.27090(12) 0.45142(12) 0.2396(5) 0.0298(6) Uani 1 1 d . . . H7 H 0.2970 0.4680 0.1204 0.036 Uiso 1 1 calc R . . C8 C 0.27801(12) 0.40532(12) 0.3469(5) 0.0319(7) Uani 1 1 d . . . C9 C 0.23935(13) 0.38196(14) 0.5281(6) 0.0405(8) Uani 1 1 d . . . H9 H 0.2121 0.3438 0.5419 0.049 Uiso 1 1 calc R . . C10 C 0.24747(13) 0.42024(15) 0.6661(6) 0.0398(7) Uani 1 1 d . . . H10 H 0.2264 0.4121 0.7898 0.048 Uiso 1 1 calc R . . C11 C 0.29242(13) 0.47728(13) 0.6118(5) 0.0342(7) Uani 1 1 d . . . H11 H 0.2983 0.5043 0.7245 0.041 Uiso 1 1 calc R . . C12 C 0.37729(13) 0.47576(13) 0.7250(5) 0.0356(7) Uani 1 1 d . . . C13 C 0.36526(12) 0.40849(12) 0.4888(5) 0.0317(6) Uani 1 1 d . . . C14 C 0.43639(12) 0.43217(12) 0.7660(5) 0.0308(6) Uani 1 1 d . . . C15 C 0.42689(12) 0.41051(12) 0.9630(6) 0.0362(7) Uani 1 1 d . . . H15 H 0.3923 0.3986 1.0293 0.043 Uiso 1 1 calc R . . C16 C 0.46878(13) 0.40636(14) 1.0624(5) 0.0377(7) Uani 1 1 d . . . H16 H 0.4631 0.3919 1.1988 0.045 Uiso 1 1 calc R . . C17 C 0.51905(13) 0.42326(13) 0.9630(6) 0.0380(7) Uani 1 1 d . . . H17 H 0.5474 0.4198 1.0313 0.046 Uiso 1 1 calc R . . C18 C 0.52804(12) 0.44483(13) 0.7676(5) 0.0347(7) Uani 1 1 d . . . H18 H 0.5625 0.4562 0.7009 0.042 Uiso 1 1 calc R . . C19 C 0.48684(12) 0.45018(13) 0.6662(5) 0.0345(7) Uani 1 1 d . . . H19 H 0.4930 0.4658 0.5316 0.041 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 0.0485(2) 0.04256(19) 0.04040(18) -0.01264(15) -0.01109(16) 0.02530(16) N1 0.0344(13) 0.0398(13) 0.0285(14) -0.0077(11) -0.0084(11) 0.0246(11) N2 0.0324(12) 0.0371(13) 0.0287(14) -0.0063(11) -0.0066(10) 0.0215(11) N3 0.0352(13) 0.0426(13) 0.0282(14) -0.0074(12) -0.0062(11) 0.0260(11) O1 0.0530(14) 0.0391(12) 0.0560(18) 0.0068(13) 0.0097(13) 0.0175(11) O2 0.0631(16) 0.0436(14) 0.0609(19) -0.0121(14) -0.0147(15) 0.0221(13) O3 0.0325(11) 0.0515(13) 0.0407(14) -0.0089(10) -0.0077(9) 0.0280(10) O4 0.0383(11) 0.0486(12) 0.0447(15) -0.0088(11) -0.0136(10) 0.0274(10) O5 0.0541(14) 0.0649(15) 0.0413(15) -0.0216(13) -0.0216(12) 0.0416(13) O6 0.0483(12) 0.0435(12) 0.0368(13) -0.0045(10) -0.0038(10) 0.0311(11) C1 0.074(3) 0.045(2) 0.096(4) 0.021(2) 0.030(3) 0.015(2) C2 0.0385(17) 0.0402(17) 0.050(2) -0.0049(16) -0.0040(16) 0.0251(15) C3 0.0338(15) 0.0426(17) 0.0326(17) -0.0026(14) -0.0025(13) 0.0251(14) C4 0.0382(17) 0.0489(18) 0.0358(19) -0.0046(15) -0.0096(14) 0.0259(15) C5 0.056(2) 0.059(2) 0.050(2) 0.0032(18) -0.0096(18) 0.0358(19) C6 0.0377(17) 0.069(2) 0.066(3) -0.007(2) -0.0035(19) 0.0276(18) C7 0.0294(14) 0.0396(15) 0.0250(16) 0.0001(12) -0.0035(12) 0.0207(13) C8 0.0328(14) 0.0344(15) 0.0298(18) 0.0015(13) -0.0009(13) 0.0177(13) C9 0.0360(16) 0.0434(18) 0.041(2) 0.0040(15) -0.0006(15) 0.0193(15) C10 0.0408(17) 0.060(2) 0.0263(18) -0.0033(15) -0.0021(14) 0.0311(16) C11 0.0365(16) 0.0465(17) 0.0289(18) -0.0032(14) -0.0030(13) 0.0278(14) C12 0.0370(16) 0.0436(17) 0.0328(18) -0.0076(14) -0.0106(13) 0.0252(14) C13 0.0354(14) 0.0388(15) 0.0261(16) 0.0001(13) 0.0032(13) 0.0223(13) C14 0.0294(14) 0.0390(15) 0.0308(18) -0.0019(13) -0.0036(12) 0.0222(12) C15 0.0351(16) 0.0404(16) 0.0367(18) 0.0071(16) 0.0057(15) 0.0215(13) C16 0.0408(17) 0.0433(17) 0.0310(17) 0.0093(14) 0.0042(14) 0.0225(14) C17 0.0370(15) 0.0436(17) 0.039(2) 0.0083(15) -0.0037(15) 0.0239(13) C18 0.0328(15) 0.0408(16) 0.035(2) 0.0075(14) 0.0050(13) 0.0216(13) C19 0.0397(16) 0.0437(16) 0.0274(18) 0.0020(14) -0.0010(14) 0.0262(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 Br C8 1.945(3) . ? N1 C12 1.384(4) . ? N1 N2 1.447(3) . ? N1 C11 1.487(4) . ? N2 C13 1.398(4) . ? N2 C8 1.475(4) . ? N3 C13 1.389(4) . ? N3 C12 1.396(4) . ? N3 C14 1.438(4) . ? O1 C2 1.340(5) . ? O1 C1 1.458(5) . ? O2 C2 1.189(5) . ? O3 C3 1.419(3) . ? O3 C4 1.446(4) . ? O4 C7 1.408(4) . ? O4 C4 1.432(4) . ? O5 C12 1.193(4) . ? O6 C13 1.210(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.523(5) . ? C3 C11 1.538(5) . ? C3 C7 1.557(4) . ? C4 C6 1.491(5) . ? C4 C5 1.524(5) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.555(4) . ? C7 H7 1.0000 . ? C8 C9 1.501(5) . ? C9 C10 1.320(5) . ? C9 H9 0.9500 . ? C10 C11 1.490(5) . ? C10 H10 0.9500 . ? C11 H11 1.0000 . ? C14 C15 1.378(5) . ? C14 C19 1.390(4) . ? C15 C16 1.385(5) . ? C15 H15 0.9500 . ? C16 C17 1.390(5) . ? C16 H16 0.9500 . ? C17 C18 1.368(5) . ? C17 H17 0.9500 . ? C18 C19 1.391(4) . ? C18 H18 0.9500 . ? C19 H19 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 C12 N1 N2 108.9(2) . . ? C12 N1 C11 120.4(3) . . ? N2 N1 C11 113.0(2) . . ? C13 N2 N1 107.1(2) . . ? C13 N2 C8 125.5(2) . . ? N1 N2 C8 109.1(2) . . ? C13 N3 C12 111.9(2) . . ? C13 N3 C14 124.6(2) . . ? C12 N3 C14 123.5(3) . . ? C2 O1 C1 116.4(4) . . ? C3 O3 C4 109.7(2) . . ? C7 O4 C4 110.1(2) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 O1 123.8(3) . . ? O2 C2 C3 124.5(4) . . ? O1 C2 C3 111.7(3) . . ? O3 C3 C2 108.0(2) . . ? O3 C3 C11 109.7(3) . . ? C2 C3 C11 109.6(3) . . ? O3 C3 C7 104.8(2) . . ? C2 C3 C7 116.8(3) . . ? C11 C3 C7 107.7(2) . . ? O4 C4 O3 105.6(2) . . ? O4 C4 C6 109.5(3) . . ? O3 C4 C6 108.0(3) . . ? O4 C4 C5 109.4(3) . . ? O3 C4 C5 110.4(3) . . ? C6 C4 C5 113.6(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O4 C7 C8 109.5(2) . . ? O4 C7 C3 105.4(2) . . ? C8 C7 C3 108.2(2) . . ? O4 C7 H7 111.2 . . ? C8 C7 H7 111.2 . . ? C3 C7 H7 111.2 . . ? N2 C8 C9 110.6(3) . . ? N2 C8 C7 104.2(2) . . ? C9 C8 C7 110.3(2) . . ? N2 C8 Br 110.71(19) . . ? C9 C8 Br 113.0(2) . . ? C7 C8 Br 107.7(2) . . ? C10 C9 C8 112.5(3) . . ? C10 C9 H9 123.8 . . ? C8 C9 H9 123.8 . . ? C9 C10 C11 114.4(3) . . ? C9 C10 H10 122.8 . . ? C11 C10 H10 122.8 . . ? N1 C11 C10 109.4(2) . . ? N1 C11 C3 101.9(3) . . ? C10 C11 C3 111.3(3) . . ? N1 C11 H11 111.3 . . ? C10 C11 H11 111.3 . . ? C3 C11 H11 111.3 . . ? O5 C12 N1 126.2(3) . . ? O5 C12 N3 128.6(3) . . ? N1 C12 N3 105.2(3) . . ? O6 C13 N3 126.1(3) . . ? O6 C13 N2 128.0(3) . . ? N3 C13 N2 105.8(2) . . ? C15 C14 C19 121.7(3) . . ? C15 C14 N3 119.6(3) . . ? C19 C14 N3 118.6(3) . . ? C14 C15 C16 118.7(3) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C15 C16 C17 120.2(3) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C18 C17 C16 120.6(3) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 120.2(3) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C14 C19 C18 118.6(3) . . ? C14 C19 H19 120.7 . . ? C18 C19 H19 120.7 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 66.74 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.324 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.047 #SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.020 1584 211 ' ' _platon_squeeze_details ; the asymmetric unit contains approximately one half molecule of pentane which is disordered over at least two sites. ;