# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'G. C. W. Fu' _publ_contact_author_address ; Department of Chemistry Massachusetts Ave., 18-290 Cambridge MA MA 02139-4307 UNITED STATES OF AMERICA ; _publ_contact_author_email GCF@MIT.EDU _publ_section_title ; Asymmetric [3+2] Annulations Catalyzed by a Planar-Chiral Derivative of DMAP ; loop_ _publ_author_name 'G. C. W. Fu' 'E. Bappert' 'Peter Muller' # Attachment '05261.cif' data_05261 _database_code_depnum_ccdc_archive 'CCDC 294368' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H35 F6 Fe N2 O P' _chemical_formula_weight 652.43 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 Tetragonal _symmetry_space_group_name_H-M P4(3)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 11.9811(3) _cell_length_b 11.9811(3) _cell_length_c 40.4968(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5813.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6103 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 25.43 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2704 _exptl_absorpt_coefficient_mu 0.641 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8825 _exptl_absorpt_correction_T_max 0.9686 _exptl_absorpt_process_details sadabs _exptl_special_details ; Siemens three-circle diffractometer, Bruker APEX CCD ; _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 'Bruker Smart APEX CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 124357 _diffrn_reflns_av_R_equivalents 0.0955 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -54 _diffrn_reflns_limit_l_max 54 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 28.70 _reflns_number_total 7504 _reflns_number_gt 6592 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5 (Bruker-AXS, 2003)' _computing_cell_refinement 'SAINT 5 (Bruker-AXS, 2003)' _computing_data_reduction 'SAINT 5 (Bruker-AXS, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0422P)^2^+1.6954P] 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' _refine_ls_abs_structure_Flack -0.008(14) _refine_ls_number_reflns 7504 _refine_ls_number_parameters 384 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.0904 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.02129(2) 0.98339(2) 0.082926(7) 0.01399(7) Uani 1 1 d . . . O1 O -0.14679(15) 0.73620(15) 0.03873(5) 0.0267(4) Uani 1 1 d . . . N1 N -0.17669(16) 0.92384(16) 0.03660(4) 0.0159(4) Uani 1 1 d . . . N2 N -0.07818(17) 1.26068(16) 0.04244(5) 0.0191(4) Uani 1 1 d . . . C1 C -0.06161(19) 0.94912(19) 0.04010(5) 0.0161(4) Uani 1 1 d . . . C2 C 0.03238(19) 0.87814(19) 0.04307(5) 0.0172(5) Uani 1 1 d . . . H2 H 0.0312 0.7989 0.0439 0.021 Uiso 1 1 calc R . . C3 C 0.1284(2) 0.9468(2) 0.04454(5) 0.0176(5) Uani 1 1 d . . . H3 H 0.2030 0.9206 0.0461 0.021 Uiso 1 1 calc R . . C4 C 0.09646(19) 1.0607(2) 0.04330(5) 0.0180(5) Uani 1 1 d . . . H4 H 0.1452 1.1232 0.0442 0.022 Uiso 1 1 calc R . . C5 C -0.0232(2) 1.06444(18) 0.04044(5) 0.0157(4) Uani 1 1 d . . . C6 C -0.1035(2) 1.15431(19) 0.03912(5) 0.0174(4) Uani 1 1 d . . . C7 C -0.2167(2) 1.1201(2) 0.03356(6) 0.0195(5) Uani 1 1 d . . . H7 H -0.2721 1.1759 0.0305 0.023 Uiso 1 1 calc R . . C8 C -0.24765(18) 1.0123(2) 0.03251(5) 0.0185(4) Uani 1 1 d . . . H8 H -0.3242 0.9964 0.0286 0.022 Uiso 1 1 calc R . . C9 C -0.2148(2) 0.81162(19) 0.03845(5) 0.0185(5) Uani 1 1 d . . . C10 C -0.3363(2) 0.7904(2) 0.04077(5) 0.0195(5) Uani 1 1 d . . . H10 H -0.3879 0.8502 0.0427 0.023 Uiso 1 1 calc R . . C11 C -0.3709(2) 0.6849(2) 0.04009(6) 0.0200(5) Uani 1 1 d . . . H11 H -0.3139 0.6300 0.0387 0.024 Uiso 1 1 calc R . . C12 C -0.4855(2) 0.64266(19) 0.04115(5) 0.0204(5) Uani 1 1 d . . . C13 C -0.5782(2) 0.7128(2) 0.04176(6) 0.0258(6) Uani 1 1 d . . . H13 H -0.5685 0.7914 0.0430 0.031 Uiso 1 1 calc R . . C14 C -0.6849(2) 0.6677(2) 0.04052(7) 0.0320(6) Uani 1 1 d . . . H14 H -0.7480 0.7158 0.0409 0.038 Uiso 1 1 calc R . . C15 C -0.7001(2) 0.5532(3) 0.03873(7) 0.0344(7) Uani 1 1 d . . . H15 H -0.7734 0.5233 0.0372 0.041 Uiso 1 1 calc R . . C16 C -0.6091(2) 0.4827(3) 0.03922(6) 0.0309(6) Uani 1 1 d . . . H16 H -0.6194 0.4041 0.0388 0.037 Uiso 1 1 calc R . . C17 C -0.5023(2) 0.5277(2) 0.04039(5) 0.0252(5) Uani 1 1 d . . . H17 H -0.4396 0.4792 0.0407 0.030 Uiso 1 1 calc R . . C18 C 0.0318(2) 1.3063(2) 0.05234(6) 0.0246(5) Uani 1 1 d . . . H18A H 0.0821 1.3138 0.0331 0.030 Uiso 1 1 calc R . . H18B H 0.0679 1.2585 0.0692 0.030 Uiso 1 1 calc R . . C19 C 0.0012(2) 1.4204(2) 0.06659(7) 0.0357(7) Uani 1 1 d . . . H19A H -0.0225 1.4141 0.0899 0.043 Uiso 1 1 calc R . . H19B H 0.0648 1.4729 0.0651 0.043 Uiso 1 1 calc R . . C20 C -0.0952(2) 1.4578(2) 0.04469(7) 0.0341(7) Uani 1 1 d . . . H20A H -0.1402 1.5164 0.0556 0.041 Uiso 1 1 calc R . . H20B H -0.0678 1.4865 0.0233 0.041 Uiso 1 1 calc R . . C21 C -0.1626(2) 1.3511(2) 0.04010(7) 0.0262(6) Uani 1 1 d . . . H21A H -0.2197 1.3434 0.0576 0.031 Uiso 1 1 calc R . . H21B H -0.2000 1.3503 0.0183 0.031 Uiso 1 1 calc R . . C31 C 0.1083(2) 0.9472(2) 0.12475(5) 0.0188(5) Uani 1 1 d . . . C32 C 0.0138(2) 0.87491(19) 0.12150(5) 0.0190(5) Uani 1 1 d . . . C33 C -0.0845(2) 0.9435(2) 0.12077(5) 0.0181(5) Uani 1 1 d . . . C34 C -0.0501(2) 1.0570(2) 0.12375(5) 0.0180(5) Uani 1 1 d . . . C35 C 0.0686(2) 1.0600(2) 0.12623(5) 0.0182(5) Uani 1 1 d . . . C310 C 0.2283(2) 0.9115(2) 0.12651(6) 0.0233(5) Uani 1 1 d . . . H31A H 0.2462 0.8889 0.1491 0.035 Uiso 1 1 calc R . . H31B H 0.2764 0.9739 0.1200 0.035 Uiso 1 1 calc R . . H31C H 0.2405 0.8485 0.1115 0.035 Uiso 1 1 calc R . . C320 C 0.0160(2) 0.7496(2) 0.11978(6) 0.0249(5) Uani 1 1 d . . . H32A H 0.0067 0.7187 0.1420 0.037 Uiso 1 1 calc R . . H32B H 0.0875 0.7251 0.1106 0.037 Uiso 1 1 calc R . . H32C H -0.0450 0.7235 0.1056 0.037 Uiso 1 1 calc R . . C330 C -0.2028(2) 0.9037(2) 0.11836(6) 0.0237(5) Uani 1 1 d . . . H33A H -0.2045 0.8305 0.1076 0.035 Uiso 1 1 calc R . . H33B H -0.2465 0.9570 0.1053 0.035 Uiso 1 1 calc R . . H33C H -0.2348 0.8977 0.1406 0.035 Uiso 1 1 calc R . . C340 C -0.1278(2) 1.1557(2) 0.12502(6) 0.0228(5) Uani 1 1 d . . . H34A H -0.1539 1.1665 0.1477 0.034 Uiso 1 1 calc R . . H34B H -0.1918 1.1421 0.1105 0.034 Uiso 1 1 calc R . . H34C H -0.0881 1.2227 0.1176 0.034 Uiso 1 1 calc R . . C350 C 0.1389(2) 1.1623(2) 0.13162(6) 0.0241(5) Uani 1 1 d . . . H35A H 0.1012 1.2274 0.1221 0.036 Uiso 1 1 calc R . . H35B H 0.2116 1.1522 0.1209 0.036 Uiso 1 1 calc R . . H35C H 0.1497 1.1740 0.1554 0.036 Uiso 1 1 calc R . . P1 P -0.56238(6) 1.10812(6) 0.044973(17) 0.02515(15) Uani 1 1 d . . . F1 F -0.62224(15) 0.99674(14) 0.03151(5) 0.0484(5) Uani 1 1 d . . . F2 F -0.50035(15) 1.21788(14) 0.05683(4) 0.0459(5) Uani 1 1 d . . . F3 F -0.64515(14) 1.18031(15) 0.02270(5) 0.0424(4) Uani 1 1 d . . . F4 F -0.48012(16) 1.03285(17) 0.06646(4) 0.0523(5) Uani 1 1 d . . . F5 F -0.64813(15) 1.11457(16) 0.07483(4) 0.0461(5) Uani 1 1 d . . . F6 F -0.47691(13) 1.09941(13) 0.01430(3) 0.0294(3) Uani 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 0.01348(14) 0.01535(14) 0.01313(13) -0.00003(11) -0.00044(11) -0.00019(12) O1 0.0222(10) 0.0170(9) 0.0410(10) -0.0008(8) -0.0032(8) -0.0005(7) N1 0.0128(9) 0.0172(10) 0.0176(9) -0.0014(7) -0.0026(7) -0.0004(7) N2 0.0228(11) 0.0166(10) 0.0179(9) 0.0033(8) 0.0048(8) 0.0001(8) C1 0.0170(11) 0.0173(11) 0.0142(9) 0.0008(8) 0.0004(8) -0.0014(8) C2 0.0172(11) 0.0175(11) 0.0168(10) -0.0022(8) -0.0003(9) 0.0051(9) C3 0.0152(11) 0.0203(12) 0.0172(10) -0.0026(9) 0.0001(8) 0.0042(9) C4 0.0137(11) 0.0230(12) 0.0172(10) 0.0024(9) 0.0021(8) -0.0028(9) C5 0.0169(10) 0.0169(10) 0.0133(9) 0.0012(8) 0.0008(8) -0.0026(9) C6 0.0191(11) 0.0193(11) 0.0137(10) 0.0033(8) 0.0034(8) 0.0010(9) C7 0.0174(12) 0.0201(12) 0.0209(11) 0.0034(9) 0.0003(9) 0.0023(9) C8 0.0148(10) 0.0226(12) 0.0181(10) 0.0027(9) -0.0016(8) -0.0001(10) C9 0.0210(12) 0.0171(12) 0.0173(10) 0.0000(8) -0.0020(9) -0.0024(9) C10 0.0209(12) 0.0195(12) 0.0182(11) -0.0012(9) -0.0017(9) -0.0007(9) C11 0.0188(12) 0.0221(12) 0.0191(10) 0.0012(9) -0.0027(9) 0.0010(9) C12 0.0247(12) 0.0239(11) 0.0126(10) 0.0018(8) -0.0037(9) -0.0075(11) C13 0.0283(14) 0.0221(13) 0.0269(12) 0.0046(10) -0.0027(11) -0.0029(11) C14 0.0223(14) 0.0355(16) 0.0382(15) 0.0071(12) -0.0018(11) -0.0025(11) C15 0.0264(14) 0.0492(18) 0.0275(13) 0.0013(12) 0.0003(11) -0.0200(13) C16 0.0411(16) 0.0293(13) 0.0222(12) -0.0008(11) 0.0007(11) -0.0164(14) C17 0.0322(15) 0.0231(11) 0.0201(10) 0.0009(9) 0.0000(9) -0.0054(10) C18 0.0234(13) 0.0205(12) 0.0299(12) -0.0003(9) 0.0060(10) -0.0054(10) C19 0.0355(18) 0.0250(14) 0.0466(16) -0.0096(11) 0.0097(13) -0.0072(12) C20 0.0389(16) 0.0174(14) 0.0460(16) 0.0015(11) 0.0175(13) 0.0008(11) C21 0.0285(14) 0.0182(12) 0.0318(13) 0.0041(10) 0.0083(11) 0.0054(10) C31 0.0186(12) 0.0225(12) 0.0153(10) 0.0028(8) -0.0020(9) -0.0016(9) C32 0.0185(11) 0.0226(12) 0.0160(10) 0.0034(8) -0.0013(9) -0.0014(10) C33 0.0196(12) 0.0210(12) 0.0137(9) 0.0010(8) -0.0001(8) -0.0002(9) C34 0.0190(12) 0.0213(12) 0.0135(9) 0.0008(8) 0.0009(8) 0.0006(9) C35 0.0195(12) 0.0216(12) 0.0136(10) -0.0018(8) -0.0011(8) -0.0025(9) C310 0.0211(12) 0.0262(14) 0.0226(12) 0.0032(10) -0.0051(10) 0.0004(10) C320 0.0265(13) 0.0218(12) 0.0263(12) 0.0039(9) -0.0022(11) -0.0005(11) C330 0.0200(12) 0.0293(14) 0.0217(11) 0.0011(10) 0.0025(9) -0.0059(10) C340 0.0254(13) 0.0225(13) 0.0205(11) -0.0033(9) 0.0031(9) 0.0045(10) C350 0.0256(13) 0.0240(13) 0.0226(11) -0.0052(10) -0.0015(10) -0.0055(10) P1 0.0181(3) 0.0239(3) 0.0334(3) -0.0018(3) 0.0047(3) 0.0009(3) F1 0.0428(10) 0.0296(10) 0.0729(13) -0.0130(9) 0.0217(9) -0.0123(8) F2 0.0415(11) 0.0454(10) 0.0507(10) -0.0170(8) -0.0024(8) -0.0130(9) F3 0.0290(9) 0.0402(10) 0.0580(11) -0.0034(9) -0.0079(8) 0.0107(8) F4 0.0458(10) 0.0736(13) 0.0374(9) 0.0222(9) 0.0115(8) 0.0247(11) F5 0.0368(10) 0.0514(11) 0.0499(11) -0.0086(9) 0.0230(8) 0.0026(9) F6 0.0227(7) 0.0357(8) 0.0296(7) 0.0030(6) 0.0029(6) 0.0003(7) _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 C32 2.034(2) . ? Fe1 C31 2.035(2) . ? Fe1 C1 2.040(2) . ? Fe1 C33 2.045(2) . ? Fe1 C5 2.046(2) . ? Fe1 C2 2.052(2) . ? Fe1 C35 2.059(2) . ? Fe1 C34 2.060(2) . ? Fe1 C4 2.060(2) . ? Fe1 C3 2.063(2) . ? O1 C9 1.217(3) . ? N1 C8 1.369(3) . ? N1 C1 1.419(3) . ? N1 C9 1.422(3) . ? N2 C6 1.317(3) . ? N2 C18 1.481(3) . ? N2 C21 1.485(3) . ? C1 C2 1.416(3) . ? C1 C5 1.456(3) . ? C2 C3 1.416(3) . ? C3 C4 1.418(3) . ? C4 C5 1.439(3) . ? C5 C6 1.445(3) . ? C6 C7 1.435(3) . ? C7 C8 1.344(3) . ? C9 C10 1.480(3) . ? C10 C11 1.330(3) . ? C11 C12 1.464(3) . ? C12 C17 1.392(3) . ? C12 C13 1.394(4) . ? C13 C14 1.389(4) . ? C14 C15 1.386(4) . ? C15 C16 1.380(4) . ? C16 C17 1.390(3) . ? C18 C19 1.528(3) . ? C19 C20 1.524(4) . ? C20 C21 1.523(4) . ? C31 C32 1.432(3) . ? C31 C35 1.434(3) . ? C31 C310 1.502(3) . ? C32 C33 1.436(3) . ? C32 C320 1.503(3) . ? C33 C34 1.426(3) . ? C33 C330 1.499(3) . ? C34 C35 1.426(3) . ? C34 C340 1.506(3) . ? C35 C350 1.503(3) . ? P1 F2 1.5850(17) . ? P1 F5 1.5884(17) . ? P1 F4 1.5942(18) . ? P1 F3 1.5954(18) . ? P1 F1 1.6101(18) . ? P1 F6 1.6133(16) . ? 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 C32 Fe1 C31 41.20(10) . . ? C32 Fe1 C1 120.17(9) . . ? C31 Fe1 C1 156.03(10) . . ? C32 Fe1 C33 41.21(10) . . ? C31 Fe1 C33 69.13(9) . . ? C1 Fe1 C33 106.76(9) . . ? C32 Fe1 C5 159.60(10) . . ? C31 Fe1 C5 159.09(10) . . ? C1 Fe1 C5 41.75(9) . . ? C33 Fe1 C5 125.41(9) . . ? C32 Fe1 C2 102.37(9) . . ? C31 Fe1 C2 119.37(9) . . ? C1 Fe1 C2 40.49(9) . . ? C33 Fe1 C2 119.06(9) . . ? C5 Fe1 C2 69.35(9) . . ? C32 Fe1 C35 69.08(9) . . ? C31 Fe1 C35 40.99(10) . . ? C1 Fe1 C35 161.38(10) . . ? C33 Fe1 C35 68.67(9) . . ? C5 Fe1 C35 125.19(9) . . ? C2 Fe1 C35 157.81(10) . . ? C32 Fe1 C34 68.81(9) . . ? C31 Fe1 C34 68.64(9) . . ? C1 Fe1 C34 124.49(9) . . ? C33 Fe1 C34 40.64(9) . . ? C5 Fe1 C34 111.32(9) . . ? C2 Fe1 C34 157.08(10) . . ? C35 Fe1 C34 40.50(9) . . ? C32 Fe1 C4 154.81(10) . . ? C31 Fe1 C4 121.34(9) . . ? C1 Fe1 C4 68.97(9) . . ? C33 Fe1 C4 163.66(10) . . ? C5 Fe1 C4 41.03(9) . . ? C2 Fe1 C4 68.62(9) . . ? C35 Fe1 C4 110.05(9) . . ? C34 Fe1 C4 127.90(10) . . ? C32 Fe1 C3 118.07(10) . . ? C31 Fe1 C3 105.27(9) . . ? C1 Fe1 C3 67.64(9) . . ? C33 Fe1 C3 154.22(10) . . ? C5 Fe1 C3 68.25(9) . . ? C2 Fe1 C3 40.24(9) . . ? C35 Fe1 C3 124.44(9) . . ? C34 Fe1 C3 162.59(10) . . ? C4 Fe1 C3 40.23(9) . . ? C8 N1 C1 116.76(19) . . ? C8 N1 C9 122.63(19) . . ? C1 N1 C9 120.57(19) . . ? C6 N2 C18 126.1(2) . . ? C6 N2 C21 122.8(2) . . ? C18 N2 C21 110.70(19) . . ? C2 C1 N1 130.8(2) . . ? C2 C1 C5 108.54(19) . . ? N1 C1 C5 120.7(2) . . ? C2 C1 Fe1 70.22(12) . . ? N1 C1 Fe1 126.94(15) . . ? C5 C1 Fe1 69.35(11) . . ? C3 C2 C1 107.5(2) . . ? C3 C2 Fe1 70.28(13) . . ? C1 C2 Fe1 69.29(12) . . ? C2 C3 C4 109.8(2) . . ? C2 C3 Fe1 69.48(13) . . ? C4 C3 Fe1 69.78(13) . . ? C3 C4 C5 107.6(2) . . ? C3 C4 Fe1 69.98(13) . . ? C5 C4 Fe1 68.97(12) . . ? C4 C5 C6 133.6(2) . . ? C4 C5 C1 106.61(19) . . ? C6 C5 C1 119.8(2) . . ? C4 C5 Fe1 70.00(12) . . ? C6 C5 Fe1 123.94(15) . . ? C1 C5 Fe1 68.90(11) . . ? N2 C6 C7 120.7(2) . . ? N2 C6 C5 124.3(2) . . ? C7 C6 C5 115.0(2) . . ? C8 C7 C6 122.7(2) . . ? C7 C8 N1 124.7(2) . . ? O1 C9 N1 119.2(2) . . ? O1 C9 C10 122.0(2) . . ? N1 C9 C10 118.8(2) . . ? C11 C10 C9 117.9(2) . . ? C10 C11 C12 128.3(2) . . ? C17 C12 C13 118.8(2) . . ? C17 C12 C11 118.5(2) . . ? C13 C12 C11 122.7(2) . . ? C14 C13 C12 119.9(2) . . ? C15 C14 C13 120.6(3) . . ? C16 C15 C14 120.1(3) . . ? C15 C16 C17 119.4(3) . . ? C16 C17 C12 121.2(2) . . ? N2 C18 C19 102.7(2) . . ? C20 C19 C18 103.0(2) . . ? C21 C20 C19 103.1(2) . . ? N2 C21 C20 104.1(2) . . ? C32 C31 C35 108.2(2) . . ? C32 C31 C310 126.1(2) . . ? C35 C31 C310 125.7(2) . . ? C32 C31 Fe1 69.35(13) . . ? C35 C31 Fe1 70.38(12) . . ? C310 C31 Fe1 126.17(16) . . ? C31 C32 C33 107.7(2) . . ? C31 C32 C320 126.5(2) . . ? C33 C32 C320 125.8(2) . . ? C31 C32 Fe1 69.45(13) . . ? C33 C32 Fe1 69.81(12) . . ? C320 C32 Fe1 127.00(16) . . ? C34 C33 C32 107.9(2) . . ? C34 C33 C330 125.6(2) . . ? C32 C33 C330 126.5(2) . . ? C34 C33 Fe1 70.22(12) . . ? C32 C33 Fe1 68.98(13) . . ? C330 C33 Fe1 127.69(16) . . ? C35 C34 C33 108.6(2) . . ? C35 C34 C340 126.4(2) . . ? C33 C34 C340 125.0(2) . . ? C35 C34 Fe1 69.73(12) . . ? C33 C34 Fe1 69.14(12) . . ? C340 C34 Fe1 128.33(15) . . ? C34 C35 C31 107.7(2) . . ? C34 C35 C350 126.2(2) . . ? C31 C35 C350 126.0(2) . . ? C34 C35 Fe1 69.77(12) . . ? C31 C35 Fe1 68.62(12) . . ? C350 C35 Fe1 129.88(16) . . ? F2 P1 F5 91.85(10) . . ? F2 P1 F4 90.81(11) . . ? F5 P1 F4 90.68(10) . . ? F2 P1 F3 90.74(10) . . ? F5 P1 F3 90.12(10) . . ? F4 P1 F3 178.23(11) . . ? F2 P1 F1 177.55(10) . . ? F5 P1 F1 90.58(10) . . ? F4 P1 F1 89.51(12) . . ? F3 P1 F1 88.91(11) . . ? F2 P1 F6 89.38(9) . . ? F5 P1 F6 178.75(10) . . ? F4 P1 F6 89.50(9) . . ? F3 P1 F6 89.67(9) . . ? F1 P1 F6 88.18(9) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.70 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.542 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.066 # Attachment 'GF106T.CIF' data_gf106t _database_code_depnum_ccdc_archive 'CCDC 294369' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H17 Br O' _chemical_formula_sum 'C20 H17 Br O' _chemical_formula_weight 353.25 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.2277(14) _cell_length_b 14.583(3) _cell_length_c 15.656(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1650.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 926 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 25.45 _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 2.490 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.6358 _exptl_absorpt_correction_T_max 0.7888 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer equipped with an oxford low-temperature apparatus perating at 193 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3\% per frame for 30 s, such that a hemisphere was collected. A total of 1271 frames were collected with a final resolution of 0.80 \%A. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Absorption corrections were applied using SADABS based on Blessing,(1995). The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V6.1. All H atoms were found by difference fourier methods and refined isotropically. ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD' _diffrn_measurement_method '\w, 0.3 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9518 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.88 _reflns_number_total 3593 _reflns_number_gt 2987 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ASTRO (BRUKER, V5.007, 1997)' _computing_cell_refinement 'SMART (BRUKER, V5.625, 2001)' _computing_data_reduction 'SAINT (BRUKER, V6.22, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (BRUKER, 2000, V6.1)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, 1997, V5.1)' _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^)+(0.0354P)^2^+0.0000P] 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 refall _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 0.015(9) _refine_ls_number_reflns 3593 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0728 _refine_ls_wR_factor_gt 0.0694 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.74604(4) 0.284300(19) 0.818391(18) 0.05285(11) Uani 1 1 d . . . O1 O 0.1265(3) -0.27011(13) 0.94631(13) 0.0436(5) Uani 1 1 d . . . C1 C 0.1321(4) -0.18900(19) 0.93100(18) 0.0352(6) Uani 1 1 d . . . C2 C 0.3044(4) -0.13290(18) 0.9164(2) 0.0348(6) Uani 1 1 d . . . H2 H 0.398(4) -0.1609(18) 0.9463(19) 0.034(7) Uiso 1 1 d . . . H1 H 0.343(4) -0.135(2) 0.853(2) 0.056(9) Uiso 1 1 d . . . C3 C 0.2457(4) -0.03542(16) 0.93952(15) 0.0287(5) Uani 1 1 d . . . H3 H 0.237(4) -0.0301(14) 1.0002(15) 0.021(5) Uiso 1 1 d . . . C4 C 0.0386(3) -0.02803(17) 0.91061(17) 0.0280(5) Uani 1 1 d . . . C5 C 0.0101(3) -0.01203(17) 0.8152(2) 0.0283(5) Uani 1 1 d . . . C6 C 0.0597(3) 0.0642(2) 0.76657(18) 0.0351(6) Uani 1 1 d . . . H4 H 0.126(4) 0.1145(19) 0.7932(17) 0.038(8) Uiso 1 1 d . . . C7 C 0.0112(4) 0.0673(2) 0.6815(2) 0.0416(7) Uani 1 1 d . . . H5 H 0.041(4) 0.122(2) 0.6419(19) 0.049(9) Uiso 1 1 d . . . C8 C -0.0865(4) -0.0039(2) 0.6447(2) 0.0442(7) Uani 1 1 d . . . H6 H -0.113(4) -0.0030(18) 0.586(2) 0.046(9) Uiso 1 1 d . . . C9 C -0.1422(4) -0.0776(2) 0.69214(19) 0.0405(7) Uani 1 1 d . . . H7 H -0.210(4) -0.1249(18) 0.6672(16) 0.039(8) Uiso 1 1 d . . . C10 C -0.0939(3) -0.08181(18) 0.77810(17) 0.0304(6) Uani 1 1 d . . . C11 C -0.1452(3) -0.15081(18) 0.84295(17) 0.0331(6) Uani 1 1 d . . . C12 C -0.0378(4) -0.12696(17) 0.92264(18) 0.0313(6) Uani 1 1 d . . . H8 H -0.101(3) -0.1314(16) 0.9698(17) 0.024(7) Uiso 1 1 d . . . C13 C -0.0656(4) 0.0441(2) 0.9618(2) 0.0358(6) Uani 1 1 d . . . H10 H -0.016(4) 0.109(2) 0.950(2) 0.049(9) Uiso 1 1 d . . . H9 H -0.050(3) 0.0336(16) 1.0186(18) 0.021(6) Uiso 1 1 d . . . H11 H -0.193(4) 0.0406(18) 0.9472(18) 0.041(8) Uiso 1 1 d . . . C14 C -0.2643(4) -0.21916(19) 0.8344(2) 0.0439(6) Uani 1 1 d . . . H12 H -0.316(4) -0.228(2) 0.782(2) 0.044(8) Uiso 1 1 d . . . H13 H -0.286(4) -0.2564(19) 0.8792(17) 0.031(7) Uiso 1 1 d . . . C15 C 0.3713(3) 0.04077(17) 0.90858(17) 0.0288(6) Uani 1 1 d . . . C16 C 0.3889(4) 0.12043(19) 0.95702(18) 0.0352(6) Uani 1 1 d . . . H14 H 0.320(4) 0.1253(17) 1.0056(17) 0.032(7) Uiso 1 1 d . . . C17 C 0.4961(4) 0.1941(2) 0.9300(2) 0.0414(7) Uani 1 1 d . . . H15 H 0.510(4) 0.2469(19) 0.9651(17) 0.043(8) Uiso 1 1 d . . . C18 C 0.5898(3) 0.18633(18) 0.85365(18) 0.0349(6) Uani 1 1 d . . . C19 C 0.5791(3) 0.1090(2) 0.80446(18) 0.0343(6) Uani 1 1 d . . . H16 H 0.640(4) 0.1043(18) 0.7553(17) 0.031(7) Uiso 1 1 d . . . C20 C 0.4695(3) 0.03623(19) 0.83237(18) 0.0315(6) Uani 1 1 d . . . H17 H 0.466(3) -0.0152(17) 0.7994(16) 0.019(7) 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 Br1 0.06132(19) 0.05017(17) 0.04706(17) 0.00514(14) -0.0026(2) -0.02553(16) O1 0.0444(11) 0.0340(11) 0.0525(13) 0.0096(9) -0.0111(10) -0.0070(8) C1 0.0397(14) 0.0365(15) 0.0294(14) 0.0028(12) -0.0009(12) -0.0036(12) C2 0.0267(14) 0.0341(14) 0.0435(17) 0.0042(13) -0.0037(12) 0.0033(10) C3 0.0263(11) 0.0353(12) 0.0244(11) 0.0012(9) -0.0031(14) -0.0014(12) C4 0.0242(12) 0.0306(13) 0.0291(13) -0.0011(11) 0.0005(11) -0.0014(10) C5 0.0219(11) 0.0342(13) 0.0290(13) -0.0010(13) 0.0024(12) 0.0056(9) C6 0.0253(13) 0.0420(16) 0.0381(16) 0.0034(13) -0.0007(12) 0.0024(11) C7 0.0323(14) 0.0548(18) 0.0377(15) 0.0140(16) 0.0022(15) 0.0081(12) C8 0.0400(16) 0.067(2) 0.0254(15) 0.0017(15) -0.0031(13) 0.0109(15) C9 0.0321(14) 0.0517(18) 0.0376(17) -0.0104(14) -0.0062(13) 0.0059(12) C10 0.0212(12) 0.0382(15) 0.0317(13) -0.0048(12) 0.0001(11) 0.0045(10) C11 0.0241(12) 0.0359(14) 0.0392(16) -0.0044(12) -0.0035(11) 0.0036(11) C12 0.0287(13) 0.0360(15) 0.0293(14) 0.0023(12) 0.0045(12) -0.0042(10) C13 0.0310(16) 0.0442(17) 0.0322(16) -0.0055(14) 0.0043(13) 0.0023(13) C14 0.0353(14) 0.0416(14) 0.0547(19) -0.0019(15) -0.0076(17) -0.0041(14) C15 0.0208(12) 0.0333(14) 0.0322(14) 0.0007(11) -0.0057(11) 0.0028(10) C16 0.0353(15) 0.0417(16) 0.0286(14) -0.0033(13) 0.0009(13) -0.0009(11) C17 0.0473(16) 0.0367(16) 0.0401(17) -0.0060(13) -0.0014(14) -0.0045(13) C18 0.0305(13) 0.0347(14) 0.0396(15) 0.0072(12) -0.0044(12) -0.0086(11) C19 0.0250(13) 0.0445(16) 0.0335(16) -0.0003(13) 0.0010(12) -0.0007(11) C20 0.0253(12) 0.0343(14) 0.0349(16) -0.0069(13) -0.0008(11) 0.0004(10) _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 C18 1.903(2) . ? O1 C1 1.208(3) . ? C1 C2 1.507(4) . ? C1 C12 1.531(4) . ? C2 C3 1.527(3) . ? C2 H2 0.92(3) . ? C2 H1 1.02(3) . ? C3 C15 1.514(4) . ? C3 C4 1.567(4) . ? C3 H3 0.96(2) . ? C4 C13 1.521(4) . ? C4 C5 1.526(4) . ? C4 C12 1.556(3) . ? C5 C10 1.392(3) . ? C5 C6 1.394(4) . ? C6 C7 1.378(4) . ? C6 H4 0.97(3) . ? C7 C8 1.381(5) . ? C7 H5 1.03(3) . ? C8 C9 1.367(4) . ? C8 H6 0.94(3) . ? C9 C10 1.392(4) . ? C9 H7 0.93(3) . ? C10 C11 1.477(4) . ? C11 C14 1.324(4) . ? C11 C12 1.510(4) . ? C12 H8 0.87(3) . ? C13 H10 1.02(3) . ? C13 H9 0.91(3) . ? C13 H11 0.95(3) . ? C14 H12 0.91(3) . ? C14 H13 0.90(3) . ? C15 C20 1.390(4) . ? C15 C16 1.393(4) . ? C16 C17 1.390(4) . ? C16 H14 0.91(3) . ? C17 C18 1.379(4) . ? C17 H15 0.95(3) . ? C18 C19 1.368(4) . ? C19 C20 1.394(4) . ? C19 H16 0.89(3) . ? C20 H17 0.91(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 O1 C1 C2 126.1(3) . . ? O1 C1 C12 124.7(3) . . ? C2 C1 C12 109.2(2) . . ? C1 C2 C3 103.9(2) . . ? C1 C2 H2 106.8(17) . . ? C3 C2 H2 119.8(17) . . ? C1 C2 H1 110.7(18) . . ? C3 C2 H1 109.8(17) . . ? H2 C2 H1 106(3) . . ? C15 C3 C2 116.2(2) . . ? C15 C3 C4 115.4(2) . . ? C2 C3 C4 105.1(2) . . ? C15 C3 H3 107.5(14) . . ? C2 C3 H3 109.3(13) . . ? C4 C3 H3 102.4(17) . . ? C13 C4 C5 110.1(2) . . ? C13 C4 C12 113.7(2) . . ? C5 C4 C12 102.3(2) . . ? C13 C4 C3 111.6(2) . . ? C5 C4 C3 115.0(2) . . ? C12 C4 C3 103.90(19) . . ? C10 C5 C6 119.6(3) . . ? C10 C5 C4 111.7(2) . . ? C6 C5 C4 128.5(2) . . ? C7 C6 C5 119.3(3) . . ? C7 C6 H4 121.1(16) . . ? C5 C6 H4 119.6(16) . . ? C6 C7 C8 120.6(3) . . ? C6 C7 H5 123.8(17) . . ? C8 C7 H5 115.7(16) . . ? C9 C8 C7 121.0(3) . . ? C9 C8 H6 118.9(18) . . ? C7 C8 H6 120.1(18) . . ? C8 C9 C10 119.1(3) . . ? C8 C9 H7 120.6(16) . . ? C10 C9 H7 120.2(16) . . ? C9 C10 C5 120.4(3) . . ? C9 C10 C11 129.2(2) . . ? C5 C10 C11 110.3(2) . . ? C14 C11 C10 127.4(3) . . ? C14 C11 C12 126.3(3) . . ? C10 C11 C12 106.4(2) . . ? C11 C12 C1 110.3(2) . . ? C11 C12 C4 107.2(2) . . ? C1 C12 C4 105.9(2) . . ? C11 C12 H8 114.6(16) . . ? C1 C12 H8 107.6(16) . . ? C4 C12 H8 110.9(16) . . ? C4 C13 H10 111.5(18) . . ? C4 C13 H9 109.9(16) . . ? H10 C13 H9 107(2) . . ? C4 C13 H11 108.5(17) . . ? H10 C13 H11 110(2) . . ? H9 C13 H11 110(2) . . ? C11 C14 H12 117.3(19) . . ? C11 C14 H13 119.4(16) . . ? H12 C14 H13 123(2) . . ? C20 C15 C16 117.4(2) . . ? C20 C15 C3 123.1(2) . . ? C16 C15 C3 119.5(2) . . ? C17 C16 C15 122.0(3) . . ? C17 C16 H14 119.9(16) . . ? C15 C16 H14 117.9(16) . . ? C18 C17 C16 118.3(3) . . ? C18 C17 H15 121.0(17) . . ? C16 C17 H15 120.6(17) . . ? C19 C18 C17 121.9(2) . . ? C19 C18 Br1 119.3(2) . . ? C17 C18 Br1 118.8(2) . . ? C18 C19 C20 118.9(3) . . ? C18 C19 H16 121.4(18) . . ? C20 C19 H16 119.7(18) . . ? C15 C20 C19 121.5(3) . . ? C15 C20 H17 120.7(15) . . ? C19 C20 H17 117.8(15) . . ? 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 O1 C1 C2 C3 -155.6(3) . . . . ? C12 C1 C2 C3 24.9(3) . . . . ? C1 C2 C3 C15 -163.7(2) . . . . ? C1 C2 C3 C4 -34.7(3) . . . . ? C15 C3 C4 C13 -76.2(3) . . . . ? C2 C3 C4 C13 154.4(2) . . . . ? C15 C3 C4 C5 50.0(3) . . . . ? C2 C3 C4 C5 -79.3(3) . . . . ? C15 C3 C4 C12 160.9(2) . . . . ? C2 C3 C4 C12 31.6(3) . . . . ? C13 C4 C5 C10 -112.2(2) . . . . ? C12 C4 C5 C10 8.8(3) . . . . ? C3 C4 C5 C10 120.7(2) . . . . ? C13 C4 C5 C6 61.7(3) . . . . ? C12 C4 C5 C6 -177.3(2) . . . . ? C3 C4 C5 C6 -65.4(3) . . . . ? C10 C5 C6 C7 -2.6(4) . . . . ? C4 C5 C6 C7 -176.1(2) . . . . ? C5 C6 C7 C8 0.4(4) . . . . ? C6 C7 C8 C9 2.1(4) . . . . ? C7 C8 C9 C10 -2.2(4) . . . . ? C8 C9 C10 C5 -0.1(4) . . . . ? C8 C9 C10 C11 176.4(3) . . . . ? C6 C5 C10 C9 2.5(3) . . . . ? C4 C5 C10 C9 177.1(2) . . . . ? C6 C5 C10 C11 -174.6(2) . . . . ? C4 C5 C10 C11 -0.1(3) . . . . ? C9 C10 C11 C14 -7.2(4) . . . . ? C5 C10 C11 C14 169.6(3) . . . . ? C9 C10 C11 C12 174.0(2) . . . . ? C5 C10 C11 C12 -9.1(3) . . . . ? C14 C11 C12 C1 80.8(3) . . . . ? C10 C11 C12 C1 -100.4(2) . . . . ? C14 C11 C12 C4 -164.3(3) . . . . ? C10 C11 C12 C4 14.5(3) . . . . ? O1 C1 C12 C11 -69.0(4) . . . . ? C2 C1 C12 C11 110.5(3) . . . . ? O1 C1 C12 C4 175.3(3) . . . . ? C2 C1 C12 C4 -5.2(3) . . . . ? C13 C4 C12 C11 104.6(3) . . . . ? C5 C4 C12 C11 -14.0(2) . . . . ? C3 C4 C12 C11 -133.9(2) . . . . ? C13 C4 C12 C1 -137.6(2) . . . . ? C5 C4 C12 C1 103.8(2) . . . . ? C3 C4 C12 C1 -16.1(3) . . . . ? C2 C3 C15 C20 33.1(3) . . . . ? C4 C3 C15 C20 -90.7(3) . . . . ? C2 C3 C15 C16 -148.1(2) . . . . ? C4 C3 C15 C16 88.2(3) . . . . ? C20 C15 C16 C17 1.6(4) . . . . ? C3 C15 C16 C17 -177.3(3) . . . . ? C15 C16 C17 C18 -1.3(4) . . . . ? C16 C17 C18 C19 0.3(4) . . . . ? C16 C17 C18 Br1 -177.1(2) . . . . ? C17 C18 C19 C20 0.3(4) . . . . ? Br1 C18 C19 C20 177.68(19) . . . . ? C16 C15 C20 C19 -1.1(4) . . . . ? C3 C15 C20 C19 177.8(2) . . . . ? C18 C19 C20 C15 0.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.492 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.050