# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email guigen.li@ttu.edu _publ_contact_author_name 'Guigen Li' loop_ _publ_author_name 'Zhiliang Yuan' 'Liangyong Mei' 'Yin Wei' 'Min Shi' 'Padmanabha Kattamuri' 'Patrick Mcdowell' 'Guigen Li' data_cd201396 _database_code_depnum_ccdc_archive 'CCDC 785244' #TrackingRef '- cd201396.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C55 H43 Cl2 N2 O2 P S' _chemical_formula_weight 897.84 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' Cl Cl 0.1484 0.1585 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M C222(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 13.5209(9) _cell_length_b 16.5318(12) _cell_length_c 41.077(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9181.8(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5619 _cell_measurement_theta_min 4.368 _cell_measurement_theta_max 42.612 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.397 _exptl_crystal_size_mid 0.365 _exptl_crystal_size_min 0.258 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3744 _exptl_absorpt_coefficient_mu 0.267 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.20075 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _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_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24246 _diffrn_reflns_av_R_equivalents 0.0956 _diffrn_reflns_av_sigmaI/netI 0.0852 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.50 _reflns_number_total 8529 _reflns_number_gt 6184 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0386P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(6) _chemical_absolute_configuration ad _refine_ls_number_reflns 8529 _refine_ls_number_parameters 569 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0650 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 0.909 _refine_ls_restrained_S_all 0.909 _refine_ls_shift/su_max 0.003 _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 P1 P 0.94014(6) 0.78502(5) 0.926087(19) 0.0496(2) Uani 1 1 d . . . S1 S 0.69894(5) 0.93798(5) 0.807172(18) 0.0465(2) Uani 1 1 d . . . Cl1 Cl 0.24924(11) 0.38740(14) 0.99342(4) 0.1746(9) Uani 1 1 d . . . Cl2 Cl 0.07216(11) 0.33216(9) 0.96371(4) 0.1240(5) Uani 1 1 d . . . N1 N 0.72691(15) 0.85533(14) 0.82860(5) 0.0388(6) Uani 1 1 d . . . N2 N 0.70315(16) 0.78954(16) 0.87681(5) 0.0443(6) Uani 1 1 d . . . O1 O 0.75665(14) 1.00232(13) 0.81972(5) 0.0576(6) Uani 1 1 d . . . O2 O 0.70711(14) 0.91400(14) 0.77434(5) 0.0599(6) Uani 1 1 d . . . C1 C 0.73899(18) 0.85202(18) 0.86304(6) 0.0366(6) Uani 1 1 d . . . C2 C 0.64931(19) 0.74192(18) 0.85249(7) 0.0429(7) Uani 1 1 d . . . H2 H 0.6738 0.6861 0.8530 0.051 Uiso 1 1 calc R . . C3 C 0.67498(19) 0.78030(18) 0.81872(6) 0.0420(7) Uani 1 1 d . . . H3 H 0.6133 0.7951 0.8077 0.050 Uiso 1 1 calc R . . C4 C 0.7349(2) 0.72708(18) 0.79629(7) 0.0444(7) Uani 1 1 d . . . C5 C 0.6883(3) 0.6858(2) 0.77175(9) 0.0756(11) Uani 1 1 d . . . H5 H 0.6209 0.6930 0.7684 0.091 Uiso 1 1 calc R . . C6 C 0.7414(4) 0.6330(3) 0.75172(10) 0.0916(13) Uani 1 1 d . . . H6 H 0.7092 0.6044 0.7353 0.110 Uiso 1 1 calc R . . C7 C 0.8403(3) 0.6236(2) 0.75629(10) 0.0777(11) Uani 1 1 d . . . H7 H 0.8762 0.5887 0.7430 0.093 Uiso 1 1 calc R . . C8 C 0.8858(3) 0.6647(2) 0.77991(9) 0.0738(11) Uani 1 1 d . . . H8 H 0.9536 0.6585 0.7828 0.089 Uiso 1 1 calc R . . C9 C 0.8341(2) 0.7164(2) 0.80028(8) 0.0614(9) Uani 1 1 d . . . H9 H 0.8672 0.7440 0.8167 0.074 Uiso 1 1 calc R . . C10 C 0.5392(2) 0.74137(18) 0.85812(7) 0.0444(7) Uani 1 1 d . . . C11 C 0.4924(2) 0.8043(2) 0.87404(8) 0.0547(8) Uani 1 1 d . . . H11 H 0.5297 0.8458 0.8832 0.066 Uiso 1 1 calc R . . C12 C 0.3904(3) 0.8061(3) 0.87649(10) 0.0756(11) Uani 1 1 d . . . H12 H 0.3592 0.8487 0.8872 0.091 Uiso 1 1 calc R . . C13 C 0.3358(3) 0.7455(3) 0.86322(11) 0.0897(14) Uani 1 1 d . . . H13 H 0.2672 0.7469 0.8648 0.108 Uiso 1 1 calc R . . C14 C 0.3808(3) 0.6829(3) 0.84774(10) 0.0900(14) Uani 1 1 d . . . H14 H 0.3429 0.6414 0.8389 0.108 Uiso 1 1 calc R . . C15 C 0.4823(2) 0.6807(2) 0.84511(8) 0.0681(10) Uani 1 1 d . . . H15 H 0.5125 0.6378 0.8344 0.082 Uiso 1 1 calc R . . C16 C 0.79009(19) 0.91759(17) 0.88102(6) 0.0382(6) Uani 1 1 d . . . C17 C 0.7317(2) 0.97106(19) 0.89927(7) 0.0491(8) Uani 1 1 d . . . H17 H 0.6636 0.9632 0.9001 0.059 Uiso 1 1 calc R . . C18 C 0.7723(2) 1.0338(2) 0.91570(8) 0.0560(9) Uani 1 1 d . . . H18 H 0.7318 1.0688 0.9274 0.067 Uiso 1 1 calc R . . C19 C 0.8757(2) 1.04671(18) 0.91522(7) 0.0481(8) Uani 1 1 d . . . C20 C 0.9186(3) 1.1139(2) 0.93064(8) 0.0665(10) Uani 1 1 d . . . H20 H 0.8786 1.1504 0.9418 0.080 Uiso 1 1 calc R . . C21 C 1.0167(3) 1.1260(2) 0.92950(9) 0.0792(12) Uani 1 1 d . . . H21 H 1.0443 1.1715 0.9392 0.095 Uiso 1 1 calc R . . C22 C 1.0772(3) 1.0697(2) 0.91361(9) 0.0709(10) Uani 1 1 d . . . H22 H 1.1452 1.0779 0.9131 0.085 Uiso 1 1 calc R . . C23 C 1.0389(2) 1.0040(2) 0.89906(7) 0.0525(8) Uani 1 1 d . . . H23 H 1.0808 0.9667 0.8892 0.063 Uiso 1 1 calc R . . C24 C 0.9359(2) 0.99107(17) 0.89855(6) 0.0415(7) Uani 1 1 d . . . C25 C 0.89295(18) 0.92472(17) 0.88159(6) 0.0359(6) Uani 1 1 d . . . C26 C 0.95679(18) 0.86158(17) 0.86639(6) 0.0385(6) Uani 1 1 d . . . C27 C 1.00153(19) 0.87610(19) 0.83522(7) 0.0425(7) Uani 1 1 d . . . C28 C 0.9894(2) 0.9499(2) 0.81862(7) 0.0531(8) Uani 1 1 d . . . H28 H 0.9482 0.9895 0.8272 0.064 Uiso 1 1 calc R . . C29 C 1.0372(2) 0.9638(2) 0.79029(8) 0.0681(10) Uani 1 1 d . . . H29 H 1.0295 1.0134 0.7799 0.082 Uiso 1 1 calc R . . C30 C 1.0978(3) 0.9052(3) 0.77633(9) 0.0777(12) Uani 1 1 d . . . H30 H 1.1300 0.9157 0.7568 0.093 Uiso 1 1 calc R . . C31 C 1.1098(2) 0.8335(3) 0.79128(8) 0.0694(11) Uani 1 1 d . . . H31 H 1.1496 0.7944 0.7816 0.083 Uiso 1 1 calc R . . C32 C 1.0632(2) 0.8160(2) 0.82135(7) 0.0492(8) Uani 1 1 d . . . C33 C 1.0764(2) 0.7421(2) 0.83787(8) 0.0535(8) Uani 1 1 d . . . H33 H 1.1127 0.7009 0.8282 0.064 Uiso 1 1 calc R . . C34 C 1.0364(2) 0.7307(2) 0.86786(7) 0.0507(8) Uani 1 1 d . . . H34 H 1.0472 0.6821 0.8787 0.061 Uiso 1 1 calc R . . C35 C 0.97835(19) 0.79143(18) 0.88295(7) 0.0418(7) Uani 1 1 d . . . C36 C 0.9422(2) 0.67623(18) 0.93384(7) 0.0478(7) Uani 1 1 d . . . C37 C 0.8580(2) 0.6329(2) 0.92630(9) 0.0667(10) Uani 1 1 d . . . H37 H 0.8050 0.6591 0.9164 0.080 Uiso 1 1 calc R . . C38 C 0.8510(3) 0.5523(2) 0.93306(10) 0.0844(13) Uani 1 1 d . . . H38 H 0.7934 0.5246 0.9276 0.101 Uiso 1 1 calc R . . C39 C 0.9264(3) 0.5116(2) 0.94754(9) 0.0772(11) Uani 1 1 d . . . H39 H 0.9209 0.4566 0.9521 0.093 Uiso 1 1 calc R . . C40 C 1.0099(3) 0.5528(2) 0.95521(10) 0.0785(11) Uani 1 1 d . . . H40 H 1.0626 0.5260 0.9650 0.094 Uiso 1 1 calc R . . C41 C 1.0170(2) 0.6339(2) 0.94860(9) 0.0716(11) Uani 1 1 d . . . H41 H 1.0746 0.6612 0.9543 0.086 Uiso 1 1 calc R . . C42 C 1.0530(3) 0.82018(18) 0.94622(7) 0.0537(8) Uani 1 1 d . . . C43 C 1.1490(3) 0.8060(2) 0.93511(9) 0.0736(11) Uani 1 1 d . . . H43 H 1.1592 0.7768 0.9161 0.088 Uiso 1 1 calc R . . C44 C 1.2292(3) 0.8355(3) 0.95248(10) 0.0925(14) Uani 1 1 d . . . H44 H 1.2930 0.8260 0.9449 0.111 Uiso 1 1 calc R . . C45 C 1.2159(4) 0.8780(3) 0.98044(11) 0.1066(18) Uani 1 1 d . . . H45 H 1.2704 0.8975 0.9918 0.128 Uiso 1 1 calc R . . C46 C 1.1252(4) 0.8919(3) 0.99171(10) 0.1056(17) Uani 1 1 d . . . H46 H 1.1166 0.9209 1.0109 0.127 Uiso 1 1 calc R . . C47 C 1.0427(3) 0.8628(2) 0.97467(9) 0.0821(12) Uani 1 1 d . . . H47 H 0.9797 0.8727 0.9828 0.099 Uiso 1 1 calc R . . C48 C 0.5736(2) 0.95965(17) 0.81520(7) 0.0432(7) Uani 1 1 d . . . C49 C 0.5486(2) 1.00992(19) 0.84025(7) 0.0519(8) Uani 1 1 d . . . H49 H 0.5977 1.0350 0.8525 0.062 Uiso 1 1 calc R . . C50 C 0.4506(2) 1.0233(2) 0.84734(9) 0.0634(9) Uani 1 1 d . . . H50 H 0.4340 1.0579 0.8643 0.076 Uiso 1 1 calc R . . C51 C 0.3765(2) 0.9864(2) 0.82967(9) 0.0598(9) Uani 1 1 d . . . C52 C 0.4018(2) 0.9386(2) 0.80405(8) 0.0638(9) Uani 1 1 d . . . H52 H 0.3523 0.9157 0.7913 0.077 Uiso 1 1 calc R . . C53 C 0.5004(2) 0.9235(2) 0.79660(7) 0.0579(9) Uani 1 1 d . . . H53 H 0.5170 0.8896 0.7794 0.069 Uiso 1 1 calc R . . C54 C 0.2687(2) 1.0021(3) 0.83775(11) 0.0925(13) Uani 1 1 d . . . H54A H 0.2382 1.0311 0.8202 0.139 Uiso 1 1 calc R . . H54B H 0.2645 1.0336 0.8573 0.139 Uiso 1 1 calc R . . H54C H 0.2353 0.9515 0.8409 0.139 Uiso 1 1 calc R . . C55 C 0.1965(3) 0.3187(3) 0.96687(11) 0.1106(16) Uani 1 1 d . . . H55A H 0.2265 0.3248 0.9455 0.133 Uiso 1 1 calc R . . H55B H 0.2099 0.2643 0.9745 0.133 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 P1 0.0510(5) 0.0486(5) 0.0493(5) 0.0005(4) 0.0070(4) 0.0021(4) S1 0.0428(4) 0.0517(5) 0.0449(4) 0.0103(4) 0.0058(3) -0.0006(4) Cl1 0.1182(11) 0.283(3) 0.1228(12) -0.0531(14) 0.0154(9) -0.0334(13) Cl2 0.1283(11) 0.1076(10) 0.1362(11) -0.0281(8) -0.0119(9) 0.0222(8) N1 0.0363(12) 0.0417(14) 0.0385(13) -0.0035(11) 0.0029(10) -0.0013(11) N2 0.0350(12) 0.0525(16) 0.0455(13) 0.0065(13) -0.0024(11) -0.0071(12) O1 0.0474(12) 0.0476(13) 0.0778(15) 0.0144(11) 0.0026(10) -0.0124(11) O2 0.0567(13) 0.0823(17) 0.0409(11) 0.0130(11) 0.0111(10) 0.0036(12) C1 0.0252(13) 0.0452(18) 0.0393(16) -0.0020(13) 0.0019(12) 0.0015(13) C2 0.0353(15) 0.0420(18) 0.0514(17) 0.0000(14) 0.0005(13) -0.0011(13) C3 0.0333(14) 0.0496(18) 0.0431(16) -0.0024(14) 0.0000(12) -0.0014(14) C4 0.0431(16) 0.0459(18) 0.0440(17) -0.0024(14) 0.0026(13) -0.0052(14) C5 0.060(2) 0.088(3) 0.079(2) -0.032(2) -0.005(2) -0.005(2) C6 0.102(3) 0.099(3) 0.074(3) -0.047(3) -0.001(2) -0.017(3) C7 0.086(3) 0.067(3) 0.080(3) -0.026(2) 0.022(2) -0.004(2) C8 0.058(2) 0.074(3) 0.089(3) -0.028(2) 0.013(2) 0.0037(19) C9 0.0480(18) 0.067(2) 0.069(2) -0.0261(19) 0.0024(16) 0.0040(17) C10 0.0398(16) 0.0504(19) 0.0429(16) 0.0073(14) 0.0036(13) -0.0077(15) C11 0.0355(17) 0.064(2) 0.065(2) 0.0054(18) 0.0030(15) -0.0043(16) C12 0.047(2) 0.092(3) 0.088(3) 0.015(2) 0.0118(19) 0.010(2) C13 0.038(2) 0.137(4) 0.094(3) 0.018(3) 0.000(2) -0.013(3) C14 0.064(3) 0.125(4) 0.081(3) -0.006(3) -0.002(2) -0.047(3) C15 0.053(2) 0.080(3) 0.071(2) -0.010(2) 0.0022(17) -0.0323(19) C16 0.0347(15) 0.0410(17) 0.0391(15) 0.0026(13) 0.0012(12) -0.0029(13) C17 0.0382(16) 0.057(2) 0.0527(18) -0.0042(16) 0.0077(14) 0.0035(15) C18 0.055(2) 0.058(2) 0.0549(19) -0.0168(16) 0.0085(15) 0.0080(16) C19 0.058(2) 0.045(2) 0.0405(16) -0.0043(15) -0.0030(14) -0.0016(15) C20 0.083(3) 0.059(2) 0.057(2) -0.0180(17) -0.0059(19) -0.005(2) C21 0.099(3) 0.063(3) 0.075(3) -0.014(2) -0.033(2) -0.022(2) C22 0.056(2) 0.078(3) 0.078(2) -0.004(2) -0.0146(18) -0.018(2) C23 0.0407(18) 0.056(2) 0.061(2) -0.0049(16) -0.0073(14) -0.0110(16) C24 0.0442(17) 0.0438(17) 0.0367(15) -0.0009(13) -0.0047(13) -0.0030(15) C25 0.0319(14) 0.0406(17) 0.0352(14) 0.0064(13) 0.0020(11) -0.0023(13) C26 0.0280(14) 0.0454(17) 0.0422(16) -0.0084(13) -0.0023(12) -0.0065(13) C27 0.0317(15) 0.055(2) 0.0405(17) -0.0061(15) -0.0005(13) -0.0049(14) C28 0.0429(17) 0.075(2) 0.0409(17) -0.0014(17) 0.0047(14) -0.0014(16) C29 0.061(2) 0.089(3) 0.054(2) 0.0144(19) 0.0051(17) -0.010(2) C30 0.061(2) 0.124(4) 0.048(2) 0.011(2) 0.0180(18) 0.003(2) C31 0.0431(19) 0.113(4) 0.052(2) -0.017(2) 0.0100(16) 0.004(2) C32 0.0300(15) 0.075(2) 0.0429(17) -0.0136(16) -0.0006(14) -0.0043(16) C33 0.0345(16) 0.064(2) 0.062(2) -0.0233(18) 0.0006(15) 0.0052(15) C34 0.0424(16) 0.052(2) 0.058(2) -0.0080(16) -0.0018(15) 0.0025(15) C35 0.0327(15) 0.0448(18) 0.0479(17) -0.0066(15) 0.0012(12) -0.0024(14) C36 0.0394(16) 0.0538(18) 0.0502(18) 0.0011(14) 0.0050(15) 0.0001(16) C37 0.0441(18) 0.059(2) 0.097(3) 0.015(2) -0.0173(18) -0.0045(17) C38 0.052(2) 0.067(3) 0.135(4) 0.015(3) -0.025(2) -0.017(2) C39 0.061(2) 0.050(2) 0.121(3) 0.018(2) -0.004(2) -0.010(2) C40 0.061(2) 0.064(3) 0.111(3) 0.028(2) -0.018(2) 0.005(2) C41 0.051(2) 0.061(2) 0.103(3) 0.019(2) -0.0168(19) -0.0075(18) C42 0.073(2) 0.0449(18) 0.0434(18) 0.0003(14) 0.0042(17) -0.0163(17) C43 0.070(2) 0.084(3) 0.067(2) -0.014(2) 0.001(2) -0.025(2) C44 0.077(3) 0.123(4) 0.078(3) 0.007(3) -0.001(2) -0.043(3) C45 0.139(4) 0.120(4) 0.061(3) -0.001(3) -0.006(3) -0.085(4) C46 0.153(4) 0.107(4) 0.057(3) -0.021(2) 0.015(3) -0.066(3) C47 0.103(3) 0.083(3) 0.060(2) -0.009(2) 0.017(2) -0.027(3) C48 0.0411(16) 0.0421(17) 0.0465(17) 0.0079(14) -0.0032(13) 0.0021(13) C49 0.0454(18) 0.0466(19) 0.064(2) -0.0069(16) -0.0079(16) -0.0022(16) C50 0.052(2) 0.055(2) 0.083(2) -0.0158(18) 0.0048(18) 0.0141(17) C51 0.0431(18) 0.058(2) 0.078(2) -0.0005(19) -0.0024(17) 0.0061(17) C52 0.0502(19) 0.071(2) 0.070(2) -0.005(2) -0.0196(17) 0.0070(18) C53 0.062(2) 0.070(2) 0.0418(18) -0.0007(16) -0.0105(15) 0.0069(18) C54 0.043(2) 0.103(3) 0.131(3) -0.022(3) -0.005(2) 0.015(2) C55 0.114(4) 0.127(4) 0.091(3) -0.010(3) 0.000(3) 0.045(3) _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 P1 C36 1.827(3) . ? P1 C42 1.831(3) . ? P1 C35 1.849(3) . ? S1 O2 1.410(2) . ? S1 O1 1.416(2) . ? S1 N1 1.669(2) . ? S1 C48 1.763(3) . ? Cl1 C55 1.728(5) . ? Cl2 C55 1.701(4) . ? N1 C1 1.425(3) . ? N1 C3 1.482(3) . ? N2 C1 1.274(3) . ? N2 C2 1.466(4) . ? C1 C16 1.482(4) . ? C2 C10 1.506(4) . ? C2 C3 1.564(4) . ? C2 H2 0.9800 . ? C3 C4 1.510(4) . ? C3 H3 0.9800 . ? C4 C9 1.362(4) . ? C4 C5 1.371(4) . ? C5 C6 1.398(5) . ? C5 H5 0.9300 . ? C6 C7 1.360(6) . ? C6 H6 0.9300 . ? C7 C8 1.334(5) . ? C7 H7 0.9300 . ? C8 C9 1.385(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.372(4) . ? C10 C11 1.383(4) . ? C11 C12 1.383(4) . ? C11 H11 0.9300 . ? C12 C13 1.359(6) . ? C12 H12 0.9300 . ? C13 C14 1.358(6) . ? C13 H13 0.9300 . ? C14 C15 1.377(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C25 1.396(3) . ? C16 C17 1.403(4) . ? C17 C18 1.354(4) . ? C17 H17 0.9300 . ? C18 C19 1.415(4) . ? C18 H18 0.9300 . ? C19 C20 1.404(4) . ? C19 C24 1.406(4) . ? C20 C21 1.342(5) . ? C20 H20 0.9300 . ? C21 C22 1.401(5) . ? C21 H21 0.9300 . ? C22 C23 1.343(5) . ? C22 H22 0.9300 . ? C23 C24 1.409(4) . ? C23 H23 0.9300 . ? C24 C25 1.423(4) . ? C25 C26 1.491(4) . ? C26 C35 1.376(4) . ? C26 C27 1.437(4) . ? C27 C28 1.407(4) . ? C27 C32 1.417(4) . ? C28 C29 1.351(4) . ? C28 H28 0.9300 . ? C29 C30 1.392(5) . ? C29 H29 0.9300 . ? C30 C31 1.346(5) . ? C30 H30 0.9300 . ? C31 C32 1.416(4) . ? C31 H31 0.9300 . ? C32 C33 1.409(4) . ? C33 C34 1.359(4) . ? C33 H33 0.9300 . ? C34 C35 1.417(4) . ? C34 H34 0.9300 . ? C36 C41 1.371(4) . ? C36 C37 1.381(4) . ? C37 C38 1.364(5) . ? C37 H37 0.9300 . ? C38 C39 1.359(5) . ? C38 H38 0.9300 . ? C39 C40 1.356(5) . ? C39 H39 0.9300 . ? C40 C41 1.371(5) . ? C40 H40 0.9300 . ? C41 H41 0.9300 . ? C42 C47 1.372(4) . ? C42 C43 1.396(5) . ? C43 C44 1.386(5) . ? C43 H43 0.9300 . ? C44 C45 1.358(6) . ? C44 H44 0.9300 . ? C45 C46 1.330(6) . ? C45 H45 0.9300 . ? C46 C47 1.402(6) . ? C46 H46 0.9300 . ? C47 H47 0.9300 . ? C48 C49 1.365(4) . ? C48 C53 1.386(4) . ? C49 C50 1.375(4) . ? C49 H49 0.9300 . ? C50 C51 1.380(4) . ? C50 H50 0.9300 . ? C51 C52 1.360(4) . ? C51 C54 1.516(4) . ? C52 C53 1.391(4) . ? C52 H52 0.9300 . ? C53 H53 0.9300 . ? C54 H54A 0.9600 . ? C54 H54B 0.9600 . ? C54 H54C 0.9600 . ? C55 H55A 0.9700 . ? C55 H55B 0.9700 . ? 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 C36 P1 C42 102.77(14) . . ? C36 P1 C35 102.67(13) . . ? C42 P1 C35 100.47(13) . . ? O2 S1 O1 121.07(13) . . ? O2 S1 N1 104.86(13) . . ? O1 S1 N1 107.33(12) . . ? O2 S1 C48 108.14(13) . . ? O1 S1 C48 107.99(14) . . ? N1 S1 C48 106.59(12) . . ? C1 N1 C3 107.1(2) . . ? C1 N1 S1 125.52(19) . . ? C3 N1 S1 115.69(17) . . ? C1 N2 C2 108.8(2) . . ? N2 C1 N1 115.4(2) . . ? N2 C1 C16 123.3(2) . . ? N1 C1 C16 121.3(2) . . ? N2 C2 C10 112.9(2) . . ? N2 C2 C3 106.1(2) . . ? C10 C2 C3 111.0(2) . . ? N2 C2 H2 108.9 . . ? C10 C2 H2 108.9 . . ? C3 C2 H2 108.9 . . ? N1 C3 C4 113.6(2) . . ? N1 C3 C2 101.6(2) . . ? C4 C3 C2 115.1(2) . . ? N1 C3 H3 108.7 . . ? C4 C3 H3 108.7 . . ? C2 C3 H3 108.7 . . ? C9 C4 C5 118.5(3) . . ? C9 C4 C3 122.0(3) . . ? C5 C4 C3 119.5(3) . . ? C4 C5 C6 120.5(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 119.7(4) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C8 C7 C6 119.7(4) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 121.4(3) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C4 C9 C8 120.2(3) . . ? C4 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C15 C10 C11 118.5(3) . . ? C15 C10 C2 119.9(3) . . ? C11 C10 C2 121.4(3) . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 119.7(4) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C12 120.5(4) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 120.2(4) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C10 C15 C14 120.6(4) . . ? C10 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C25 C16 C17 119.9(3) . . ? C25 C16 C1 122.3(2) . . ? C17 C16 C1 117.7(2) . . ? C18 C17 C16 121.4(3) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C17 C18 C19 120.6(3) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C20 C19 C24 119.9(3) . . ? C20 C19 C18 121.4(3) . . ? C24 C19 C18 118.7(3) . . ? C21 C20 C19 120.7(3) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C20 C21 C22 119.6(3) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C23 C22 C21 121.3(3) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C22 C23 C24 120.7(3) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C19 C24 C23 117.7(3) . . ? C19 C24 C25 120.4(3) . . ? C23 C24 C25 121.8(3) . . ? C16 C25 C24 118.7(2) . . ? C16 C25 C26 120.7(3) . . ? C24 C25 C26 120.5(2) . . ? C35 C26 C27 119.5(3) . . ? C35 C26 C25 120.4(2) . . ? C27 C26 C25 120.0(3) . . ? C28 C27 C32 118.8(3) . . ? C28 C27 C26 121.9(3) . . ? C32 C27 C26 119.3(3) . . ? C29 C28 C27 120.6(3) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C28 C29 C30 121.2(4) . . ? C28 C29 H29 119.4 . . ? C30 C29 H29 119.4 . . ? C31 C30 C29 119.7(3) . . ? C31 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? C30 C31 C32 121.6(4) . . ? C30 C31 H31 119.2 . . ? C32 C31 H31 119.2 . . ? C33 C32 C31 122.7(3) . . ? C33 C32 C27 119.3(3) . . ? C31 C32 C27 118.0(3) . . ? C34 C33 C32 120.5(3) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C33 C34 C35 121.2(3) . . ? C33 C34 H34 119.4 . . ? C35 C34 H34 119.4 . . ? C26 C35 C34 119.9(3) . . ? C26 C35 P1 117.6(2) . . ? C34 C35 P1 122.2(2) . . ? C41 C36 C37 116.3(3) . . ? C41 C36 P1 126.2(2) . . ? C37 C36 P1 117.3(2) . . ? C38 C37 C36 121.2(3) . . ? C38 C37 H37 119.4 . . ? C36 C37 H37 119.4 . . ? C39 C38 C37 121.4(3) . . ? C39 C38 H38 119.3 . . ? C37 C38 H38 119.3 . . ? C40 C39 C38 118.5(3) . . ? C40 C39 H39 120.8 . . ? C38 C39 H39 120.8 . . ? C39 C40 C41 120.3(3) . . ? C39 C40 H40 119.9 . . ? C41 C40 H40 119.9 . . ? C36 C41 C40 122.4(3) . . ? C36 C41 H41 118.8 . . ? C40 C41 H41 118.8 . . ? C47 C42 C43 117.3(3) . . ? C47 C42 P1 117.6(3) . . ? C43 C42 P1 125.1(2) . . ? C44 C43 C42 120.0(4) . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? C45 C44 C43 120.9(4) . . ? C45 C44 H44 119.6 . . ? C43 C44 H44 119.6 . . ? C46 C45 C44 120.4(4) . . ? C46 C45 H45 119.8 . . ? C44 C45 H45 119.8 . . ? C45 C46 C47 120.0(4) . . ? C45 C46 H46 120.0 . . ? C47 C46 H46 120.0 . . ? C42 C47 C46 121.4(4) . . ? C42 C47 H47 119.3 . . ? C46 C47 H47 119.3 . . ? C49 C48 C53 120.1(3) . . ? C49 C48 S1 120.2(2) . . ? C53 C48 S1 119.7(2) . . ? C48 C49 C50 119.8(3) . . ? C48 C49 H49 120.1 . . ? C50 C49 H49 120.1 . . ? C49 C50 C51 121.2(3) . . ? C49 C50 H50 119.4 . . ? C51 C50 H50 119.4 . . ? C52 C51 C50 118.8(3) . . ? C52 C51 C54 120.7(3) . . ? C50 C51 C54 120.5(3) . . ? C51 C52 C53 121.1(3) . . ? C51 C52 H52 119.5 . . ? C53 C52 H52 119.5 . . ? C48 C53 C52 119.1(3) . . ? C48 C53 H53 120.5 . . ? C52 C53 H53 120.5 . . ? C51 C54 H54A 109.5 . . ? C51 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C51 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? Cl2 C55 Cl1 111.7(3) . . ? Cl2 C55 H55A 109.3 . . ? Cl1 C55 H55A 109.3 . . ? Cl2 C55 H55B 109.3 . . ? Cl1 C55 H55B 109.3 . . ? H55A C55 H55B 107.9 . . ? 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 O2 S1 N1 C1 172.9(2) . . . . ? O1 S1 N1 C1 42.9(2) . . . . ? C48 S1 N1 C1 -72.6(2) . . . . ? O2 S1 N1 C3 -49.0(2) . . . . ? O1 S1 N1 C3 -178.97(18) . . . . ? C48 S1 N1 C3 65.5(2) . . . . ? C2 N2 C1 N1 -5.9(3) . . . . ? C2 N2 C1 C16 174.1(2) . . . . ? C3 N1 C1 N2 -1.0(3) . . . . ? S1 N1 C1 N2 140.0(2) . . . . ? C3 N1 C1 C16 179.0(2) . . . . ? S1 N1 C1 C16 -40.0(3) . . . . ? C1 N2 C2 C10 -111.8(3) . . . . ? C1 N2 C2 C3 9.9(3) . . . . ? C1 N1 C3 C4 -117.5(2) . . . . ? S1 N1 C3 C4 97.2(2) . . . . ? C1 N1 C3 C2 6.7(2) . . . . ? S1 N1 C3 C2 -138.60(18) . . . . ? N2 C2 C3 N1 -9.9(3) . . . . ? C10 C2 C3 N1 113.1(2) . . . . ? N2 C2 C3 C4 113.4(3) . . . . ? C10 C2 C3 C4 -123.7(3) . . . . ? N1 C3 C4 C9 39.1(4) . . . . ? C2 C3 C4 C9 -77.6(4) . . . . ? N1 C3 C4 C5 -143.2(3) . . . . ? C2 C3 C4 C5 100.2(3) . . . . ? C9 C4 C5 C6 1.1(5) . . . . ? C3 C4 C5 C6 -176.7(4) . . . . ? C4 C5 C6 C7 -1.1(7) . . . . ? C5 C6 C7 C8 0.2(7) . . . . ? C6 C7 C8 C9 0.7(6) . . . . ? C5 C4 C9 C8 -0.2(5) . . . . ? C3 C4 C9 C8 177.6(3) . . . . ? C7 C8 C9 C4 -0.7(6) . . . . ? N2 C2 C10 C15 -158.4(3) . . . . ? C3 C2 C10 C15 82.7(3) . . . . ? N2 C2 C10 C11 26.8(4) . . . . ? C3 C2 C10 C11 -92.1(3) . . . . ? C15 C10 C11 C12 -0.5(5) . . . . ? C2 C10 C11 C12 174.4(3) . . . . ? C10 C11 C12 C13 0.1(6) . . . . ? C11 C12 C13 C14 0.4(6) . . . . ? C12 C13 C14 C15 -0.6(7) . . . . ? C11 C10 C15 C14 0.3(5) . . . . ? C2 C10 C15 C14 -174.6(3) . . . . ? C13 C14 C15 C10 0.2(6) . . . . ? N2 C1 C16 C25 102.0(3) . . . . ? N1 C1 C16 C25 -78.0(3) . . . . ? N2 C1 C16 C17 -74.7(4) . . . . ? N1 C1 C16 C17 105.4(3) . . . . ? C25 C16 C17 C18 5.0(4) . . . . ? C1 C16 C17 C18 -178.3(3) . . . . ? C16 C17 C18 C19 -0.8(5) . . . . ? C17 C18 C19 C20 176.5(3) . . . . ? C17 C18 C19 C24 -2.8(5) . . . . ? C24 C19 C20 C21 0.4(5) . . . . ? C18 C19 C20 C21 -178.9(3) . . . . ? C19 C20 C21 C22 -2.0(6) . . . . ? C20 C21 C22 C23 0.9(6) . . . . ? C21 C22 C23 C24 1.9(5) . . . . ? C20 C19 C24 C23 2.2(4) . . . . ? C18 C19 C24 C23 -178.5(3) . . . . ? C20 C19 C24 C25 -177.2(3) . . . . ? C18 C19 C24 C25 2.1(4) . . . . ? C22 C23 C24 C19 -3.4(4) . . . . ? C22 C23 C24 C25 176.0(3) . . . . ? C17 C16 C25 C24 -5.5(4) . . . . ? C1 C16 C25 C24 177.9(2) . . . . ? C17 C16 C25 C26 171.0(3) . . . . ? C1 C16 C25 C26 -5.6(4) . . . . ? C19 C24 C25 C16 2.0(4) . . . . ? C23 C24 C25 C16 -177.4(3) . . . . ? C19 C24 C25 C26 -174.5(2) . . . . ? C23 C24 C25 C26 6.1(4) . . . . ? C16 C25 C26 C35 -81.5(3) . . . . ? C24 C25 C26 C35 95.0(3) . . . . ? C16 C25 C26 C27 102.7(3) . . . . ? C24 C25 C26 C27 -80.9(3) . . . . ? C35 C26 C27 C28 -174.0(3) . . . . ? C25 C26 C27 C28 1.9(4) . . . . ? C35 C26 C27 C32 3.2(4) . . . . ? C25 C26 C27 C32 179.0(2) . . . . ? C32 C27 C28 C29 -1.2(4) . . . . ? C26 C27 C28 C29 175.9(3) . . . . ? C27 C28 C29 C30 1.4(5) . . . . ? C28 C29 C30 C31 -0.3(6) . . . . ? C29 C30 C31 C32 -1.0(6) . . . . ? C30 C31 C32 C33 -178.4(3) . . . . ? C30 C31 C32 C27 1.1(5) . . . . ? C28 C27 C32 C33 179.6(3) . . . . ? C26 C27 C32 C33 2.3(4) . . . . ? C28 C27 C32 C31 0.0(4) . . . . ? C26 C27 C32 C31 -177.3(3) . . . . ? C31 C32 C33 C34 174.8(3) . . . . ? C27 C32 C33 C34 -4.8(4) . . . . ? C32 C33 C34 C35 1.7(4) . . . . ? C27 C26 C35 C34 -6.2(4) . . . . ? C25 C26 C35 C34 177.9(2) . . . . ? C27 C26 C35 P1 167.69(19) . . . . ? C25 C26 C35 P1 -8.2(3) . . . . ? C33 C34 C35 C26 3.9(4) . . . . ? C33 C34 C35 P1 -169.7(2) . . . . ? C36 P1 C35 C26 161.0(2) . . . . ? C42 P1 C35 C26 -93.2(2) . . . . ? C36 P1 C35 C34 -25.2(3) . . . . ? C42 P1 C35 C34 80.6(3) . . . . ? C42 P1 C36 C41 -5.4(3) . . . . ? C35 P1 C36 C41 98.6(3) . . . . ? C42 P1 C36 C37 169.7(2) . . . . ? C35 P1 C36 C37 -86.3(3) . . . . ? C41 C36 C37 C38 -0.5(5) . . . . ? P1 C36 C37 C38 -176.1(3) . . . . ? C36 C37 C38 C39 0.2(6) . . . . ? C37 C38 C39 C40 -0.1(6) . . . . ? C38 C39 C40 C41 0.5(6) . . . . ? C37 C36 C41 C40 0.9(5) . . . . ? P1 C36 C41 C40 176.0(3) . . . . ? C39 C40 C41 C36 -0.9(6) . . . . ? C36 P1 C42 C47 -107.3(3) . . . . ? C35 P1 C42 C47 147.0(3) . . . . ? C36 P1 C42 C43 71.8(3) . . . . ? C35 P1 C42 C43 -33.9(3) . . . . ? C47 C42 C43 C44 -0.7(5) . . . . ? P1 C42 C43 C44 -179.8(3) . . . . ? C42 C43 C44 C45 0.3(6) . . . . ? C43 C44 C45 C46 0.2(7) . . . . ? C44 C45 C46 C47 -0.2(8) . . . . ? C43 C42 C47 C46 0.8(5) . . . . ? P1 C42 C47 C46 179.9(3) . . . . ? C45 C46 C47 C42 -0.3(7) . . . . ? O2 S1 C48 C49 -156.8(2) . . . . ? O1 S1 C48 C49 -24.1(3) . . . . ? N1 S1 C48 C49 90.9(2) . . . . ? O2 S1 C48 C53 25.2(3) . . . . ? O1 S1 C48 C53 157.8(2) . . . . ? N1 S1 C48 C53 -87.1(3) . . . . ? C53 C48 C49 C50 1.2(5) . . . . ? S1 C48 C49 C50 -176.8(2) . . . . ? C48 C49 C50 C51 0.4(5) . . . . ? C49 C50 C51 C52 -2.6(5) . . . . ? C49 C50 C51 C54 -179.8(4) . . . . ? C50 C51 C52 C53 3.3(5) . . . . ? C54 C51 C52 C53 -179.6(4) . . . . ? C49 C48 C53 C52 -0.6(5) . . . . ? S1 C48 C53 C52 177.4(3) . . . . ? C51 C52 C53 C48 -1.7(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C14 H14 O1 0.93 2.70 3.613(5) 169.0 5_445 C30 H30 O2 0.93 2.55 3.363(4) 146.7 3_756 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.284 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.040 # Attachment '- mo_dm1055_0m.cif' data_mo_dm1055_0m _database_code_depnum_ccdc_archive 'CCDC 798183' #TrackingRef '- mo_dm1055_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 Br2 F2 N2 O2' _chemical_formula_weight 538.19 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.249(4) _cell_length_b 5.5446(19) _cell_length_c 16.208(6) _cell_angle_alpha 90.00 _cell_angle_beta 104.895(4) _cell_angle_gamma 90.00 _cell_volume 1063.8(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4154 _cell_measurement_theta_min 2.408 _cell_measurement_theta_max 26.626 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.405 _exptl_crystal_size_mid 0.297 _exptl_crystal_size_min 0.198 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.680 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 3.849 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3083 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6946 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0588 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3597 _reflns_number_gt 2767 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0712P)^2^+0.4555P] 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 SHELXL _refine_ls_extinction_coef 0.009(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.066(17) _chemical_absolute_configuration ad _refine_ls_number_reflns 3597 _refine_ls_number_parameters 280 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1486 _refine_ls_wR_factor_gt 0.1386 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.000 _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 0.57616(7) 0.2238(2) 0.07891(4) 0.1053(4) Uani 1 1 d . . . Br2 Br 1.15523(9) 0.2732(3) 1.01050(5) 0.1384(6) Uani 1 1 d . . . F1 F 0.6376(3) 0.6419(7) 0.4742(2) 0.0721(10) Uani 1 1 d . . . F2 F 0.5928(2) 0.2713(7) 0.49209(19) 0.0704(10) Uani 1 1 d . . . O1 O 0.7870(3) 0.6504(7) 0.6256(3) 0.0636(10) Uani 1 1 d . . . O2 O 1.0116(3) 0.3794(9) 0.5773(3) 0.0692(11) Uani 1 1 d . . . N1 N 0.8214(4) 0.1192(7) 0.4998(3) 0.0483(9) Uani 1 1 d D . . N2 N 0.8734(3) 0.1257(8) 0.5877(3) 0.0452(9) Uani 1 1 d D . . C1 C 0.7255(7) 0.4220(14) 0.7564(4) 0.085(2) Uani 1 1 d . . . H1 H 0.7693 0.5610 0.7676 0.101 Uiso 1 1 calc R . . C2 C 0.6983(9) 0.301(2) 0.8223(5) 0.113(3) Uani 1 1 d . . . H2 H 0.7241 0.3595 0.8776 0.135 Uiso 1 1 calc R . . C3 C 0.6352(7) 0.0991(18) 0.8086(5) 0.091(2) Uani 1 1 d . . . H3 H 0.6166 0.0208 0.8539 0.109 Uiso 1 1 calc R . . C4 C 0.5979(6) 0.0086(15) 0.7258(6) 0.092(2) Uani 1 1 d . . . H4 H 0.5550 -0.1318 0.7152 0.111 Uiso 1 1 calc R . . C5 C 0.6258(5) 0.1304(12) 0.6604(4) 0.0679(16) Uani 1 1 d . . . H5 H 0.6017 0.0699 0.6051 0.081 Uiso 1 1 calc R . . C6 C 0.6881(4) 0.3386(9) 0.6741(3) 0.0463(11) Uani 1 1 d . . . C7 C 0.7237(4) 0.4754(9) 0.6075(3) 0.0466(11) Uani 1 1 d . . . C8 C 0.6812(4) 0.4289(9) 0.5108(3) 0.0478(11) Uani 1 1 d . . . C9 C 0.7710(4) 0.3507(9) 0.4657(3) 0.0433(10) Uani 1 1 d . . . H9 H 0.8305 0.4735 0.4754 0.052 Uiso 1 1 calc R . . C10 C 0.7228(4) 0.3204(9) 0.3714(3) 0.0445(11) Uani 1 1 d . . . C11 C 0.7417(5) 0.4947(10) 0.3156(4) 0.0541(12) Uani 1 1 d . . . H11 H 0.7835 0.6315 0.3368 0.065 Uiso 1 1 calc R . . C12 C 0.6987(5) 0.4669(12) 0.2284(4) 0.0641(15) Uani 1 1 d . . . H12 H 0.7115 0.5835 0.1907 0.077 Uiso 1 1 calc R . . C13 C 0.6359(5) 0.2609(12) 0.1981(3) 0.0606(14) Uani 1 1 d . . . C14 C 0.6181(5) 0.0843(11) 0.2519(4) 0.0628(15) Uani 1 1 d . . . H14 H 0.5777 -0.0541 0.2306 0.075 Uiso 1 1 calc R . . C15 C 0.6616(5) 0.1163(10) 0.3392(3) 0.0547(12) Uani 1 1 d . . . H15 H 0.6494 -0.0016 0.3767 0.066 Uiso 1 1 calc R . . C16 C 0.9680(4) 0.2548(9) 0.6217(3) 0.0472(11) Uani 1 1 d . . . C17 C 1.0102(4) 0.2469(10) 0.7163(3) 0.0475(10) Uani 1 1 d . . . C18 C 1.0781(5) 0.4353(11) 0.7547(4) 0.0602(14) Uani 1 1 d . . . H18 H 1.0958 0.5583 0.7213 0.072 Uiso 1 1 calc R . . C19 C 1.1198(6) 0.4424(14) 0.8422(4) 0.0764(19) Uani 1 1 d . . . H19 H 1.1645 0.5708 0.8682 0.092 Uiso 1 1 calc R . . C20 C 1.0945(5) 0.2580(17) 0.8904(4) 0.0725(17) Uani 1 1 d . . . C21 C 1.0288(6) 0.0688(16) 0.8544(4) 0.085(2) Uani 1 1 d . . . H21 H 1.0124 -0.0542 0.8884 0.102 Uiso 1 1 calc R . . C22 C 0.9867(6) 0.0615(12) 0.7667(4) 0.0695(16) Uani 1 1 d . . . H22 H 0.9424 -0.0681 0.7413 0.083 Uiso 1 1 calc R . . H1A H 0.878(3) 0.098(10) 0.480(3) 0.048(14) Uiso 1 1 d D . . H2A H 0.851(4) 0.007(6) 0.614(3) 0.044(13) Uiso 1 1 d 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 0.1109(6) 0.1473(8) 0.0426(4) -0.0153(4) -0.0080(3) 0.0304(6) Br2 0.1340(8) 0.2232(16) 0.0449(4) -0.0099(6) -0.0008(4) 0.0212(9) F1 0.077(2) 0.078(2) 0.0623(19) 0.0122(16) 0.0205(16) 0.0348(18) F2 0.0437(16) 0.111(3) 0.0557(17) -0.0061(18) 0.0109(13) -0.0282(18) O1 0.070(2) 0.053(2) 0.068(2) -0.0056(17) 0.0184(19) -0.0151(18) O2 0.051(2) 0.097(3) 0.058(2) 0.017(2) 0.0106(18) -0.023(2) N1 0.046(2) 0.047(2) 0.050(2) 0.0021(18) 0.0098(19) 0.0057(19) N2 0.040(2) 0.051(2) 0.042(2) 0.0076(17) 0.0052(17) -0.0015(18) C1 0.116(6) 0.082(5) 0.057(4) -0.011(3) 0.024(4) -0.031(4) C2 0.147(8) 0.145(9) 0.047(4) 0.000(4) 0.026(5) -0.035(7) C3 0.088(5) 0.131(7) 0.058(4) 0.037(4) 0.027(4) 0.000(5) C4 0.077(5) 0.088(5) 0.111(7) 0.030(4) 0.024(4) -0.025(4) C5 0.065(4) 0.084(4) 0.055(4) 0.003(3) 0.016(3) -0.019(3) C6 0.036(3) 0.060(3) 0.042(3) 0.002(2) 0.009(2) 0.002(2) C7 0.047(3) 0.042(3) 0.051(3) -0.004(2) 0.014(2) -0.001(2) C8 0.038(3) 0.049(3) 0.057(3) 0.004(2) 0.012(2) -0.001(2) C9 0.037(2) 0.051(3) 0.041(3) -0.001(2) 0.009(2) -0.0027(19) C10 0.038(2) 0.051(3) 0.043(3) -0.003(2) 0.006(2) 0.004(2) C11 0.054(3) 0.058(3) 0.051(3) 0.001(2) 0.016(2) -0.001(2) C12 0.070(4) 0.069(4) 0.054(3) 0.014(3) 0.018(3) 0.016(3) C13 0.065(3) 0.077(4) 0.036(2) -0.008(3) 0.006(2) 0.021(3) C14 0.058(3) 0.058(3) 0.061(4) -0.014(3) -0.006(3) 0.009(3) C15 0.056(3) 0.048(3) 0.055(3) 0.004(2) 0.007(2) 0.001(2) C16 0.036(2) 0.049(3) 0.056(3) 0.010(2) 0.011(2) 0.000(2) C17 0.040(2) 0.052(3) 0.049(3) -0.003(2) 0.0086(19) 0.000(2) C18 0.053(3) 0.063(3) 0.064(4) -0.005(3) 0.013(3) -0.010(3) C19 0.063(4) 0.090(5) 0.067(4) -0.024(4) 0.001(3) -0.008(3) C20 0.053(3) 0.109(5) 0.049(3) -0.003(4) 0.003(2) 0.013(4) C21 0.082(5) 0.116(6) 0.058(4) 0.027(4) 0.017(3) 0.003(4) C22 0.076(4) 0.074(4) 0.052(3) 0.010(3) 0.006(3) -0.014(3) _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 C13 1.893(5) . ? Br2 C20 1.899(6) . ? F1 C8 1.367(6) . ? F2 C8 1.363(6) . ? O1 C7 1.229(6) . ? O2 C16 1.216(6) . ? N1 N2 1.404(6) . ? N1 C9 1.469(6) . ? N1 H1A 0.84(2) . ? N2 C16 1.353(6) . ? N2 H2A 0.86(2) . ? C1 C2 1.373(11) . ? C1 C6 1.375(8) . ? C1 H1 0.9300 . ? C2 C3 1.345(13) . ? C2 H2 0.9300 . ? C3 C4 1.395(12) . ? C3 H3 0.9300 . ? C4 C5 1.373(9) . ? C4 H4 0.9300 . ? C5 C6 1.371(8) . ? C5 H5 0.9300 . ? C6 C7 1.474(7) . ? C7 C8 1.540(7) . ? C8 C9 1.532(7) . ? C9 C10 1.500(7) . ? C9 H9 0.9800 . ? C10 C11 1.383(7) . ? C10 C15 1.384(7) . ? C11 C12 1.384(8) . ? C11 H11 0.9300 . ? C12 C13 1.394(9) . ? C12 H12 0.9300 . ? C13 C14 1.365(9) . ? C14 C15 1.390(8) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.487(7) . ? C17 C18 1.379(8) . ? C17 C22 1.389(8) . ? C18 C19 1.380(9) . ? C18 H18 0.9300 . ? C19 C20 1.369(12) . ? C19 H19 0.9300 . ? C20 C21 1.359(12) . ? C21 C22 1.384(9) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? 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 N2 N1 C9 113.3(4) . . ? N2 N1 H1A 101(4) . . ? C9 N1 H1A 106(4) . . ? C16 N2 N1 123.0(4) . . ? C16 N2 H2A 123(4) . . ? N1 N2 H2A 111(4) . . ? C2 C1 C6 120.2(7) . . ? C2 C1 H1 119.9 . . ? C6 C1 H1 119.9 . . ? C3 C2 C1 121.5(8) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C2 C3 C4 119.3(7) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 118.8(7) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C6 C5 C4 121.8(6) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C5 C6 C1 118.2(5) . . ? C5 C6 C7 124.9(5) . . ? C1 C6 C7 116.8(5) . . ? O1 C7 C6 121.2(5) . . ? O1 C7 C8 113.8(4) . . ? C6 C7 C8 124.9(4) . . ? F2 C8 F1 104.9(4) . . ? F2 C8 C9 109.8(4) . . ? F1 C8 C9 106.6(4) . . ? F2 C8 C7 112.1(4) . . ? F1 C8 C7 106.8(4) . . ? C9 C8 C7 115.9(4) . . ? N1 C9 C10 107.6(4) . . ? N1 C9 C8 110.6(4) . . ? C10 C9 C8 112.1(4) . . ? N1 C9 H9 108.8 . . ? C10 C9 H9 108.8 . . ? C8 C9 H9 108.8 . . ? C11 C10 C15 119.4(5) . . ? C11 C10 C9 120.0(4) . . ? C15 C10 C9 120.6(4) . . ? C10 C11 C12 120.4(5) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C13 118.8(5) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C14 C13 C12 121.8(5) . . ? C14 C13 Br1 119.4(5) . . ? C12 C13 Br1 118.8(4) . . ? C13 C14 C15 118.4(5) . . ? C13 C14 H14 120.8 . . ? C15 C14 H14 120.8 . . ? C10 C15 C14 121.2(5) . . ? C10 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? O2 C16 N2 121.3(4) . . ? O2 C16 C17 122.5(5) . . ? N2 C16 C17 116.1(4) . . ? C18 C17 C22 119.2(5) . . ? C18 C17 C16 116.9(5) . . ? C22 C17 C16 123.9(5) . . ? C17 C18 C19 120.4(6) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C20 C19 C18 119.1(6) . . ? C20 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? C21 C20 C19 121.9(6) . . ? C21 C20 Br2 120.4(6) . . ? C19 C20 Br2 117.7(6) . . ? C20 C21 C22 119.1(6) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C21 C22 C17 120.3(6) . . ? C21 C22 H22 119.9 . . ? C17 C22 H22 119.9 . . ? 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 C9 N1 N2 C16 -67.7(6) . . . . ? C6 C1 C2 C3 0.1(15) . . . . ? C1 C2 C3 C4 1.0(14) . . . . ? C2 C3 C4 C5 -0.8(12) . . . . ? C3 C4 C5 C6 -0.6(11) . . . . ? C4 C5 C6 C1 1.6(9) . . . . ? C4 C5 C6 C7 178.3(6) . . . . ? C2 C1 C6 C5 -1.4(11) . . . . ? C2 C1 C6 C7 -178.3(8) . . . . ? C5 C6 C7 O1 -174.2(5) . . . . ? C1 C6 C7 O1 2.5(8) . . . . ? C5 C6 C7 C8 10.1(8) . . . . ? C1 C6 C7 C8 -173.2(6) . . . . ? O1 C7 C8 F2 -166.1(4) . . . . ? C6 C7 C8 F2 9.8(7) . . . . ? O1 C7 C8 F1 -51.8(5) . . . . ? C6 C7 C8 F1 124.2(5) . . . . ? O1 C7 C8 C9 66.8(6) . . . . ? C6 C7 C8 C9 -117.3(5) . . . . ? N2 N1 C9 C10 177.9(4) . . . . ? N2 N1 C9 C8 -59.4(5) . . . . ? F2 C8 C9 N1 -65.7(5) . . . . ? F1 C8 C9 N1 -178.8(4) . . . . ? C7 C8 C9 N1 62.5(5) . . . . ? F2 C8 C9 C10 54.3(5) . . . . ? F1 C8 C9 C10 -58.8(5) . . . . ? C7 C8 C9 C10 -177.5(4) . . . . ? N1 C9 C10 C11 -134.7(5) . . . . ? C8 C9 C10 C11 103.6(5) . . . . ? N1 C9 C10 C15 43.8(5) . . . . ? C8 C9 C10 C15 -78.0(6) . . . . ? C15 C10 C11 C12 0.8(8) . . . . ? C9 C10 C11 C12 179.2(5) . . . . ? C10 C11 C12 C13 0.2(8) . . . . ? C11 C12 C13 C14 -1.5(8) . . . . ? C11 C12 C13 Br1 179.5(4) . . . . ? C12 C13 C14 C15 1.8(8) . . . . ? Br1 C13 C14 C15 -179.3(4) . . . . ? C11 C10 C15 C14 -0.5(8) . . . . ? C9 C10 C15 C14 -178.9(5) . . . . ? C13 C14 C15 C10 -0.7(8) . . . . ? N1 N2 C16 O2 2.2(7) . . . . ? N1 N2 C16 C17 178.4(4) . . . . ? O2 C16 C17 C18 18.9(7) . . . . ? N2 C16 C17 C18 -157.3(5) . . . . ? O2 C16 C17 C22 -160.2(6) . . . . ? N2 C16 C17 C22 23.7(7) . . . . ? C22 C17 C18 C19 -1.5(9) . . . . ? C16 C17 C18 C19 179.4(5) . . . . ? C17 C18 C19 C20 1.1(10) . . . . ? C18 C19 C20 C21 -0.4(11) . . . . ? C18 C19 C20 Br2 179.2(5) . . . . ? C19 C20 C21 C22 0.3(11) . . . . ? Br2 C20 C21 C22 -179.4(5) . . . . ? C20 C21 C22 C17 -0.8(11) . . . . ? C18 C17 C22 C21 1.4(9) . . . . ? C16 C17 C22 C21 -179.6(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A O1 0.86(2) 2.16(3) 2.963(6) 155(5) 1_545 N1 H1A O2 0.84(2) 2.19(3) 2.970(6) 153(5) 2_746 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.344 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.097