# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Wenwei Lin' _publ_contact_author_email kado2099@yahoo.com.tw loop_ _publ_author_name 'Ko-Wei Chen' 'Siang-en Syu' 'Yeong-Jiunn Jang' 'Wenwei Lin' data_11226 _database_code_depnum_ccdc_archive 'CCDC 792216' #TrackingRef '11226.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H48 Cl O4 P' _chemical_formula_sum 'C42 H48 Cl O4 P' _chemical_formula_weight 683.22 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' Cl Cl 0.1484 0.1585 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.9348(3) _cell_length_b 12.1131(2) _cell_length_c 23.2120(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.0730(10) _cell_angle_gamma 90.00 _cell_volume 3915.47(14) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 37640 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.177 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.884 _exptl_absorpt_correction_T_max 1.0699 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23877 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.04 _reflns_number_total 6854 _reflns_number_gt 4664 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1399P)^2^+1.7764P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6854 _refine_ls_number_parameters 431 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1092 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.2455 _refine_ls_wR_factor_gt 0.2109 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.005 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 C1 C 0.8094(3) 0.2661(3) 0.63553(15) 0.0404(8) Uani 1 1 d . . . C2 C 0.7863(2) 0.3784(3) 0.61398(14) 0.0378(8) Uani 1 1 d . . . C3 C 0.7834(3) 0.3934(3) 0.55427(16) 0.0479(9) Uani 1 1 d . . . H3 H 0.7951 0.3333 0.5292 0.057 Uiso 1 1 calc R . . C4 C 0.7630(3) 0.4978(4) 0.53207(18) 0.0583(11) Uani 1 1 d . . . H4 H 0.7617 0.5094 0.4916 0.070 Uiso 1 1 calc R . . C5 C 0.7447(3) 0.5841(4) 0.56826(19) 0.0611(12) Uani 1 1 d . . . H5 H 0.7311 0.6551 0.5526 0.073 Uiso 1 1 calc R . . C6 C 0.7458(3) 0.5688(3) 0.62737(18) 0.0532(10) Uani 1 1 d . . . H6 H 0.7317 0.6286 0.6522 0.064 Uiso 1 1 calc R . . C7 C 0.7677(3) 0.4659(3) 0.65008(16) 0.0420(8) Uani 1 1 d . . . H7 H 0.7699 0.4554 0.6907 0.050 Uiso 1 1 calc R . . C8 C 0.8313(2) 0.1625(3) 0.72302(14) 0.0351(8) Uani 1 1 d . . . C9 C 0.9359(2) 0.1446(3) 0.72175(13) 0.0328(7) Uani 1 1 d . . . C10 C 0.9977(3) 0.2349(3) 0.72094(15) 0.0416(8) Uani 1 1 d . . . H10 H 0.9722 0.3076 0.7192 0.050 Uiso 1 1 calc R . . C11 C 1.0962(3) 0.2194(3) 0.72267(16) 0.0457(9) Uani 1 1 d . . . H11 H 1.1379 0.2815 0.7234 0.055 Uiso 1 1 calc R . . C12 C 1.1341(3) 0.1149(3) 0.72337(16) 0.0455(9) Uani 1 1 d . . . H12 H 1.2017 0.1046 0.7251 0.055 Uiso 1 1 calc R . . C13 C 1.0731(2) 0.0241(3) 0.72158(15) 0.0438(9) Uani 1 1 d . . . H13 H 1.0992 -0.0482 0.7202 0.053 Uiso 1 1 calc R . . C14 C 0.9746(2) 0.0382(3) 0.72176(14) 0.0357(8) Uani 1 1 d . . . H14 H 0.9334 -0.0243 0.7219 0.043 Uiso 1 1 calc R . . C15 C 0.7644(2) 0.1052(3) 0.75071(14) 0.0369(8) Uani 1 1 d . B . C16 C 0.7840(2) 0.0134(3) 0.79128(14) 0.0365(8) Uani 1 1 d . . . H16 H 0.7514 -0.0542 0.7838 0.044 Uiso 1 1 calc R . . C17 C 0.8437(2) 0.0174(3) 0.83764(15) 0.0373(8) Uani 1 1 d . . . C18 C 0.8595(3) -0.0708(3) 0.88060(14) 0.0409(8) Uani 1 1 d . . . C19 C 0.7920(3) -0.1523(3) 0.88817(16) 0.0513(10) Uani 1 1 d . . . H19 H 0.7341 -0.1525 0.8652 0.062 Uiso 1 1 calc R . . C20 C 0.8085(4) -0.2346(3) 0.92953(18) 0.0652(13) Uani 1 1 d . . . H20 H 0.7619 -0.2907 0.9345 0.078 Uiso 1 1 calc R . . C21 C 0.8917(4) -0.2349(4) 0.96301(19) 0.0695(14) Uani 1 1 d . . . H21 H 0.9020 -0.2905 0.9914 0.083 Uiso 1 1 calc R . . C22 C 0.9592(3) -0.1560(4) 0.95566(19) 0.0679(13) Uani 1 1 d . . . H22 H 1.0172 -0.1577 0.9784 0.081 Uiso 1 1 calc R . . C23 C 0.9443(3) -0.0724(4) 0.91510(17) 0.0543(10) Uani 1 1 d . . . H23 H 0.9914 -0.0166 0.9108 0.065 Uiso 1 1 calc R . . C24 C 0.8822(3) 0.1832(3) 0.88772(15) 0.0439(9) Uani 1 1 d . . . C25 C 0.9573(3) 0.2695(3) 0.89395(15) 0.0484(10) Uani 1 1 d . . . C26 C 1.0474(3) 0.2553(3) 0.87119(16) 0.0506(10) Uani 1 1 d . . . H26 H 1.0618 0.1891 0.8513 0.061 Uiso 1 1 calc R . . C27 C 1.1162(4) 0.3369(4) 0.87738(19) 0.0655(12) Uani 1 1 d . . . H27 H 1.1781 0.3263 0.8624 0.079 Uiso 1 1 calc R . . C28 C 1.0953(5) 0.4320(4) 0.9049(2) 0.0780(16) Uani 1 1 d . . . H28 H 1.1426 0.4883 0.9083 0.094 Uiso 1 1 calc R . . C29 C 1.0079(5) 0.4486(4) 0.9277(2) 0.0776(17) Uani 1 1 d . . . H29 H 0.9948 0.5162 0.9466 0.093 Uiso 1 1 calc R . . C30 C 0.9360(4) 0.3648(4) 0.92330(18) 0.0682(13) Uani 1 1 d . . . H30 H 0.8754 0.3745 0.9401 0.082 Uiso 1 1 calc R . . C31 C 0.6029(3) 0.1250(4) 0.6638(2) 0.0625(12) Uani 1 1 d . B . H31A H 0.5323 0.1332 0.6598 0.075 Uiso 1 1 calc R . . H31B H 0.6321 0.1845 0.6410 0.075 Uiso 1 1 calc R . . C32 C 0.6306(3) 0.0156(5) 0.6387(2) 0.0772(14) Uani 1 1 d . . . H32A H 0.6034 -0.0446 0.6620 0.093 Uiso 1 1 calc R . . H32B H 0.7014 0.0082 0.6408 0.093 Uiso 1 1 calc R . . C33 C 0.5941(5) 0.0038(6) 0.5756(3) 0.104(2) Uani 1 1 d . . . H33A H 0.6231 0.0624 0.5521 0.125 Uiso 1 1 calc R . . H33B H 0.5235 0.0138 0.5734 0.125 Uiso 1 1 calc R . . C34 C 0.6197(5) -0.1118(6) 0.5501(3) 0.1284(19) Uani 1 1 d . . . H34A H 0.5956 -0.1162 0.5100 0.193 Uiso 1 1 calc R . . H34B H 0.5900 -0.1699 0.5728 0.193 Uiso 1 1 calc R . . H34C H 0.6896 -0.1214 0.5516 0.193 Uiso 1 1 calc R . . C35 C 0.5651(3) 0.0526(4) 0.7792(2) 0.0596(11) Uani 1 1 d . B . H35A H 0.4979 0.0633 0.7650 0.071 Uiso 1 1 calc R . . H35B H 0.5831 -0.0242 0.7698 0.071 Uiso 1 1 calc R . . C36 C 0.5674(3) 0.0634(5) 0.8442(2) 0.0783(15) Uani 1 1 d . . . H36A H 0.6338 0.0466 0.8581 0.094 Uiso 1 1 calc R A 3 H36B H 0.5558 0.1422 0.8530 0.094 Uiso 1 1 calc R A 3 C37' C 0.5066(12) 0.0023(14) 0.8777(7) 0.086(4) Uiso 0.40 1 d P B 3 H37A H 0.4407 0.0246 0.8654 0.103 Uiso 0.40 1 calc PR B 3 H37B H 0.5139 -0.0753 0.8653 0.103 Uiso 0.40 1 calc PR B 3 C38' C 0.5076(15) -0.0002(18) 0.9331(9) 0.122(6) Uiso 0.40 1 d P B 3 H38A H 0.4583 -0.0515 0.9458 0.182 Uiso 0.40 1 calc PR B 3 H38B H 0.4945 0.0738 0.9479 0.182 Uiso 0.40 1 calc PR B 3 H38C H 0.5709 -0.0248 0.9478 0.182 Uiso 0.40 1 calc PR B 3 C37 C 0.5133(7) -0.0515(8) 0.8655(4) 0.074(2) Uiso 0.60 1 d P B 4 H37C H 0.4444 -0.0473 0.8538 0.089 Uiso 0.60 1 calc PR B 4 H37D H 0.5412 -0.1152 0.8453 0.089 Uiso 0.60 1 calc PR B 4 C38 C 0.5212(11) -0.0703(13) 0.9244(7) 0.143(5) Uiso 0.60 1 d P B 4 H38D H 0.4889 -0.1396 0.9335 0.215 Uiso 0.60 1 calc PR B 4 H38E H 0.4912 -0.0093 0.9448 0.215 Uiso 0.60 1 calc PR B 4 H38F H 0.5892 -0.0752 0.9364 0.215 Uiso 0.60 1 calc PR B 4 C39 C 0.6161(3) 0.2835(3) 0.7593(2) 0.0574(11) Uani 1 1 d . B . H39A H 0.6288 0.3316 0.7259 0.069 Uiso 1 1 calc R . . H39B H 0.5470 0.2904 0.7672 0.069 Uiso 1 1 calc R . . C40 C 0.6741(3) 0.3273(4) 0.8116(2) 0.0617(11) Uani 1 1 d . . . H40A H 0.7429 0.3315 0.8026 0.074 Uiso 1 1 calc R . . H40B H 0.6676 0.2762 0.8446 0.074 Uiso 1 1 calc R . . C41 C 0.6378(3) 0.4422(4) 0.8279(3) 0.0814(16) Uani 1 1 d . . . H41A H 0.6478 0.4938 0.7956 0.098 Uiso 1 1 calc R . . H41B H 0.5680 0.4385 0.8343 0.098 Uiso 1 1 calc R . . C42 C 0.6892(5) 0.4862(6) 0.8819(3) 0.1284(19) Uani 1 1 d . . . H42A H 0.6647 0.5600 0.8906 0.193 Uiso 1 1 calc R . . H42B H 0.7582 0.4906 0.8756 0.193 Uiso 1 1 calc R . . H42C H 0.6778 0.4366 0.9143 0.193 Uiso 1 1 calc R . . Cl1 Cl 0.63863(8) -0.24062(11) 0.74865(7) 0.0542(4) Uani 0.80 1 d P C 1 Cl1' Cl 0.6457(10) -0.2011(12) 0.7158(6) 0.155(5) Uiso 0.20 1 d P D 2 O1 O 0.8321(2) 0.1880(2) 0.60764(11) 0.0572(8) Uani 1 1 d . . . O2 O 0.79899(16) 0.25914(19) 0.69467(9) 0.0391(6) Uani 1 1 d . . . O3 O 0.90267(17) 0.11022(19) 0.84512(9) 0.0399(6) Uani 1 1 d . . . O4 O 0.8098(2) 0.1758(2) 0.91490(12) 0.0610(8) Uani 1 1 d . . . P1 P 0.63937(7) 0.14324(9) 0.73917(5) 0.0478(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 C1 0.042(2) 0.041(2) 0.0371(19) 0.0036(17) -0.0048(15) 0.0037(16) C2 0.0337(18) 0.039(2) 0.0403(19) 0.0060(16) -0.0025(14) 0.0039(15) C3 0.053(2) 0.049(2) 0.041(2) 0.0057(18) 0.0018(17) 0.0058(18) C4 0.068(3) 0.063(3) 0.044(2) 0.015(2) 0.0054(19) 0.007(2) C5 0.075(3) 0.046(2) 0.064(3) 0.021(2) 0.009(2) 0.009(2) C6 0.065(3) 0.037(2) 0.057(2) 0.0040(19) 0.004(2) 0.0027(18) C7 0.046(2) 0.039(2) 0.0407(19) 0.0037(16) 0.0000(15) -0.0009(16) C8 0.0368(18) 0.0330(19) 0.0351(18) 0.0021(14) -0.0052(14) 0.0057(14) C9 0.0347(18) 0.0343(19) 0.0293(16) 0.0017(14) -0.0024(13) 0.0018(14) C10 0.048(2) 0.0341(19) 0.043(2) 0.0045(16) 0.0044(16) 0.0020(16) C11 0.041(2) 0.047(2) 0.049(2) 0.0053(17) 0.0067(16) -0.0114(17) C12 0.0321(19) 0.056(3) 0.048(2) 0.0083(18) 0.0050(15) 0.0015(17) C13 0.041(2) 0.044(2) 0.047(2) 0.0060(17) 0.0047(16) 0.0062(16) C14 0.0370(18) 0.0330(19) 0.0373(18) 0.0000(15) 0.0027(14) -0.0002(15) C15 0.0313(18) 0.039(2) 0.0402(19) 0.0022(15) -0.0017(14) 0.0018(15) C16 0.0302(17) 0.0369(19) 0.0426(19) 0.0037(15) 0.0049(14) 0.0009(14) C17 0.0377(18) 0.036(2) 0.0391(19) 0.0023(15) 0.0060(15) -0.0007(15) C18 0.049(2) 0.040(2) 0.0339(18) 0.0005(15) 0.0049(15) 0.0101(16) C19 0.069(3) 0.046(2) 0.040(2) 0.0045(18) 0.0029(18) -0.013(2) C20 0.111(4) 0.039(2) 0.046(2) 0.0020(19) 0.011(2) -0.009(2) C21 0.104(4) 0.055(3) 0.050(3) 0.017(2) 0.010(3) 0.021(3) C22 0.066(3) 0.079(3) 0.058(3) 0.023(2) -0.003(2) 0.019(3) C23 0.049(2) 0.062(3) 0.052(2) 0.014(2) 0.0011(18) 0.0064(19) C24 0.058(2) 0.041(2) 0.0325(18) 0.0035(16) -0.0005(17) 0.0102(18) C25 0.076(3) 0.034(2) 0.0341(19) 0.0010(16) -0.0121(18) 0.0041(19) C26 0.067(3) 0.042(2) 0.042(2) 0.0046(17) -0.0077(18) -0.008(2) C27 0.090(3) 0.050(3) 0.056(3) 0.007(2) -0.013(2) -0.020(2) C28 0.117(5) 0.054(3) 0.062(3) 0.013(2) -0.018(3) -0.019(3) C29 0.147(6) 0.035(2) 0.049(3) -0.008(2) -0.025(3) 0.004(3) C30 0.107(4) 0.050(3) 0.046(2) -0.004(2) -0.010(2) 0.015(3) C31 0.042(2) 0.070(3) 0.074(3) 0.007(2) -0.018(2) -0.002(2) C32 0.056(3) 0.100(4) 0.075(3) -0.003(3) -0.012(2) 0.000(3) C33 0.092(4) 0.132(5) 0.085(4) -0.012(4) -0.024(3) -0.003(4) C34 0.108(4) 0.129(4) 0.147(5) -0.059(4) -0.012(3) 0.009(3) C35 0.033(2) 0.067(3) 0.079(3) 0.007(2) 0.0037(19) 0.0012(19) C36 0.048(3) 0.095(4) 0.093(4) 0.013(3) 0.017(2) 0.000(2) C39 0.037(2) 0.057(3) 0.078(3) 0.008(2) 0.0026(19) 0.0111(18) C40 0.047(2) 0.060(3) 0.078(3) -0.006(2) 0.004(2) 0.008(2) C41 0.047(3) 0.068(3) 0.129(5) -0.029(3) 0.003(3) 0.003(2) C42 0.108(4) 0.129(4) 0.147(5) -0.059(4) -0.012(3) 0.009(3) Cl1 0.0309(6) 0.0491(7) 0.0821(10) -0.0130(7) -0.0050(6) 0.0029(5) O1 0.082(2) 0.0444(16) 0.0448(15) -0.0008(13) -0.0031(13) 0.0186(14) O2 0.0418(14) 0.0382(14) 0.0373(13) 0.0077(10) -0.0003(10) 0.0083(10) O3 0.0438(14) 0.0405(14) 0.0355(13) -0.0035(11) 0.0024(10) -0.0038(11) O4 0.070(2) 0.0626(19) 0.0512(16) -0.0025(14) 0.0185(15) 0.0118(15) P1 0.0314(5) 0.0491(6) 0.0623(7) 0.0066(5) -0.0055(4) 0.0031(4) _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 C1 O1 1.196(4) . ? C1 O2 1.388(4) . ? C1 C2 1.481(5) . ? C2 C7 1.382(5) . ? C2 C3 1.397(5) . ? C3 C4 1.391(6) . ? C3 H3 0.9500 . ? C4 C5 1.370(6) . ? C4 H4 0.9500 . ? C5 C6 1.384(6) . ? C5 H5 0.9500 . ? C6 C7 1.383(5) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C15 1.344(5) . ? C8 O2 1.409(4) . ? C8 C9 1.474(4) . ? C9 C10 1.394(5) . ? C9 C14 1.397(4) . ? C10 C11 1.384(5) . ? C10 H10 0.9500 . ? C11 C12 1.371(5) . ? C11 H11 0.9500 . ? C12 C13 1.390(5) . ? C12 H12 0.9500 . ? C13 C14 1.383(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.476(5) . ? C15 P1 1.813(3) . ? C16 C17 1.337(5) . ? C16 H16 0.9500 . ? C17 O3 1.400(4) . ? C17 C18 1.473(5) . ? C18 C19 1.380(5) . ? C18 C23 1.403(5) . ? C19 C20 1.397(6) . ? C19 H19 0.9500 . ? C20 C21 1.371(7) . ? C20 H20 0.9500 . ? C21 C22 1.357(7) . ? C21 H21 0.9500 . ? C22 C23 1.393(6) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 O4 1.213(4) . ? C24 O3 1.364(4) . ? C24 C25 1.483(6) . ? C25 C30 1.379(6) . ? C25 C26 1.391(6) . ? C26 C27 1.380(6) . ? C26 H26 0.9500 . ? C27 C28 1.354(7) . ? C27 H27 0.9500 . ? C28 C29 1.359(8) . ? C28 H28 0.9500 . ? C29 C30 1.427(7) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C32 1.503(7) . ? C31 P1 1.817(4) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.541(7) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.566(9) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 C36 1.514(7) . ? C35 P1 1.792(4) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37' 1.385(16) . ? C36 C37 1.666(11) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37' C38' 1.28(2) . ? C37' H37A 0.9900 . ? C37' H37B 0.9900 . ? C38' H38A 0.9800 . ? C38' H38B 0.9800 . ? C38' H38C 0.9800 . ? C37 C38 1.385(17) . ? C37 H37C 0.9900 . ? C37 H37D 0.9900 . ? C38 H38D 0.9800 . ? C38 H38E 0.9800 . ? C38 H38F 0.9800 . ? C39 C40 1.530(6) . ? C39 P1 1.795(4) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.533(6) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C42 1.517(8) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 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 O1 C1 O2 121.8(3) . . ? O1 C1 C2 127.1(3) . . ? O2 C1 C2 111.2(3) . . ? C7 C2 C3 120.1(3) . . ? C7 C2 C1 122.9(3) . . ? C3 C2 C1 116.9(3) . . ? C4 C3 C2 119.0(4) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C5 C4 C3 120.4(4) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.7(4) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 119.5(4) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C2 C7 C6 120.3(3) . . ? C2 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C15 C8 O2 115.9(3) . . ? C15 C8 C9 129.5(3) . . ? O2 C8 C9 114.4(3) . . ? C10 C9 C14 119.0(3) . . ? C10 C9 C8 119.8(3) . . ? C14 C9 C8 121.2(3) . . ? C11 C10 C9 120.4(3) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 120.4(3) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 119.7(3) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C9 119.8(3) . . ? C13 C14 H14 120.1 . . ? C9 C14 H14 120.1 . . ? C8 C15 C16 125.3(3) . . ? C8 C15 P1 118.6(3) . . ? C16 C15 P1 116.1(2) . . ? C17 C16 C15 125.6(3) . . ? C17 C16 H16 117.2 . . ? C15 C16 H16 117.2 . . ? C16 C17 O3 118.3(3) . . ? C16 C17 C18 126.3(3) . . ? O3 C17 C18 115.2(3) . . ? C19 C18 C23 118.8(3) . . ? C19 C18 C17 121.3(3) . . ? C23 C18 C17 119.9(3) . . ? C18 C19 C20 120.1(4) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C21 C20 C19 120.4(4) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C22 C21 C20 120.2(4) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 120.7(4) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 C18 119.8(4) . . ? C22 C23 H23 120.1 . . ? C18 C23 H23 120.1 . . ? O4 C24 O3 122.0(4) . . ? O4 C24 C25 126.8(4) . . ? O3 C24 C25 111.2(3) . . ? C30 C25 C26 120.3(4) . . ? C30 C25 C24 118.4(4) . . ? C26 C25 C24 121.3(3) . . ? C27 C26 C25 120.3(4) . . ? C27 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C28 C27 C26 119.8(5) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C27 C28 C29 121.3(5) . . ? C27 C28 H28 119.3 . . ? C29 C28 H28 119.3 . . ? C28 C29 C30 120.3(5) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C25 C30 C29 117.9(5) . . ? C25 C30 H30 121.1 . . ? C29 C30 H30 121.1 . . ? C32 C31 P1 114.4(3) . . ? C32 C31 H31A 108.7 . . ? P1 C31 H31A 108.7 . . ? C32 C31 H31B 108.7 . . ? P1 C31 H31B 108.7 . . ? H31A C31 H31B 107.6 . . ? C31 C32 C33 111.7(5) . . ? C31 C32 H32A 109.3 . . ? C33 C32 H32A 109.3 . . ? C31 C32 H32B 109.3 . . ? C33 C32 H32B 109.3 . . ? H32A C32 H32B 107.9 . . ? C32 C33 C34 111.7(5) . . ? C32 C33 H33A 109.3 . . ? C34 C33 H33A 109.3 . . ? C32 C33 H33B 109.3 . . ? C34 C33 H33B 109.3 . . ? H33A C33 H33B 107.9 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C36 C35 P1 118.2(3) . . ? C36 C35 H35A 107.8 . . ? P1 C35 H35A 107.8 . . ? C36 C35 H35B 107.8 . . ? P1 C35 H35B 107.8 . . ? H35A C35 H35B 107.1 . . ? C37' C36 C35 121.5(8) . . ? C37' C36 C37 25.1(7) . . ? C35 C36 C37 103.3(5) . . ? C37' C36 H36A 106.9 . . ? C35 C36 H36A 107.0 . . ? C37 C36 H36A 99.2 . . ? C37' C36 H36B 107.0 . . ? C35 C36 H36B 107.0 . . ? C37 C36 H36B 131.7 . . ? H36A C36 H36B 106.7 . . ? C38' C37' C36 126.1(16) . . ? C38' C37' H37A 105.7 . . ? C36 C37' H37A 105.8 . . ? C38' C37' H37B 105.9 . . ? C36 C37' H37B 105.8 . . ? H37A C37' H37B 106.2 . . ? C37' C38' H38A 109.4 . . ? C37' C38' H38B 109.6 . . ? H38A C38' H38B 109.5 . . ? C37' C38' H38C 109.4 . . ? H38A C38' H38C 109.5 . . ? H38B C38' H38C 109.5 . . ? C38 C37 C36 114.2(10) . . ? C38 C37 H37C 108.7 . . ? C36 C37 H37C 108.7 . . ? C38 C37 H37D 108.8 . . ? C36 C37 H37D 108.7 . . ? H37C C37 H37D 107.6 . . ? C37 C38 H38D 109.4 . . ? C37 C38 H38E 109.6 . . ? H38D C38 H38E 109.5 . . ? C37 C38 H38F 109.4 . . ? H38D C38 H38F 109.5 . . ? H38E C38 H38F 109.5 . . ? C40 C39 P1 116.0(3) . . ? C40 C39 H39A 108.3 . . ? P1 C39 H39A 108.3 . . ? C40 C39 H39B 108.3 . . ? P1 C39 H39B 108.3 . . ? H39A C39 H39B 107.4 . . ? C39 C40 C41 109.9(4) . . ? C39 C40 H40A 109.7 . . ? C41 C40 H40A 109.7 . . ? C39 C40 H40B 109.7 . . ? C41 C40 H40B 109.7 . . ? H40A C40 H40B 108.2 . . ? C42 C41 C40 111.9(5) . . ? C42 C41 H41A 109.2 . . ? C40 C41 H41A 109.2 . . ? C42 C41 H41B 109.2 . . ? C40 C41 H41B 109.2 . . ? H41A C41 H41B 107.9 . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C1 O2 C8 118.0(3) . . ? C24 O3 C17 118.2(3) . . ? C35 P1 C39 109.4(2) . . ? C35 P1 C15 109.76(18) . . ? C39 P1 C15 112.57(18) . . ? C35 P1 C31 106.1(2) . . ? C39 P1 C31 108.6(2) . . ? C15 P1 C31 110.18(18) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.712 _refine_diff_density_min -0.475 _refine_diff_density_rms 0.117 # Attachment 'a11015.cif' data_a10115 _database_code_depnum_ccdc_archive 'CCDC 792217' #TrackingRef 'a11015.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H28 Br O' _chemical_formula_sum 'C22 H15 Br O' _chemical_formula_weight 375.25 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.7171(3) _cell_length_b 12.5408(5) _cell_length_c 17.2932(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.710(2) _cell_angle_gamma 90.00 _cell_volume 1654.31(11) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.66 _exptl_crystal_size_min 0.41 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.507 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 2.489 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2673 _exptl_absorpt_correction_T_max 0.4285 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10359 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2850 _reflns_number_gt 2342 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0251P)^2^+0.7062P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2850 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0781 _refine_ls_wR_factor_gt 0.0743 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 C1 C 0.9959(3) 0.59368(19) 0.11958(14) 0.0265(6) Uani 1 1 d . . . C2 C 1.0699(3) 0.49612(19) 0.10762(14) 0.0246(6) Uani 1 1 d . . . H2 H 1.1286 0.4854 0.0638 0.030 Uiso 1 1 calc R . . C3 C 1.0581(3) 0.41406(19) 0.15992(13) 0.0235(6) Uani 1 1 d . . . H3 H 1.1092 0.3469 0.1516 0.028 Uiso 1 1 calc R . . C4 C 0.9722(3) 0.4279(2) 0.22506(13) 0.0238(6) Uani 1 1 d . . . C5 C 0.8965(3) 0.5275(2) 0.23431(14) 0.0281(6) Uani 1 1 d . . . H5 H 0.8353 0.5386 0.2773 0.034 Uiso 1 1 calc R . . C6 C 0.9082(3) 0.6099(2) 0.18277(14) 0.0290(6) Uani 1 1 d . . . H6 H 0.8567 0.6772 0.1905 0.035 Uiso 1 1 calc R . . C7 C 0.9717(3) 0.3453(2) 0.28569(13) 0.0232(6) Uani 1 1 d . . . C8 C 0.9909(3) 0.2367(2) 0.28088(13) 0.0231(6) Uani 1 1 d . . . C9 C 0.9906(3) 0.15827(19) 0.21782(13) 0.0213(5) Uani 1 1 d . . . C10 C 0.8904(3) 0.17485(19) 0.14429(13) 0.0233(5) Uani 1 1 d . . . H10 H 0.8273 0.2396 0.1337 0.028 Uiso 1 1 calc R . . C11 C 0.8828(3) 0.0974(2) 0.08708(14) 0.0280(6) Uani 1 1 d . . . H11 H 0.8152 0.1095 0.0372 0.034 Uiso 1 1 calc R . . C12 C 0.9733(4) 0.0019(2) 0.10182(14) 0.0304(6) Uani 1 1 d . . . H12 H 0.9666 -0.0514 0.0625 0.036 Uiso 1 1 calc R . . C13 C 1.0733(4) -0.0149(2) 0.17423(14) 0.0321(6) Uani 1 1 d . . . H13 H 1.1362 -0.0797 0.1845 0.038 Uiso 1 1 calc R . . C14 C 1.0819(3) 0.0625(2) 0.23174(14) 0.0264(6) Uani 1 1 d . . . H14 H 1.1508 0.0502 0.2813 0.032 Uiso 1 1 calc R . . C15 C 0.9645(3) 0.3668(2) 0.36646(14) 0.0278(6) Uani 1 1 d . . . H15 H 0.9503 0.4352 0.3884 0.033 Uiso 1 1 calc R . . C16 C 0.9810(3) 0.2741(2) 0.40613(14) 0.0279(6) Uani 1 1 d . . . C17 C 0.9802(3) 0.2442(2) 0.48762(14) 0.0274(6) Uani 1 1 d . . . C18 C 0.9155(4) 0.3169(2) 0.53800(15) 0.0340(7) Uani 1 1 d . . . H18 H 0.8735 0.3846 0.5188 0.041 Uiso 1 1 calc R . . C19 C 0.9126(4) 0.2903(3) 0.61573(16) 0.0420(8) Uani 1 1 d . . . H19 H 0.8683 0.3397 0.6495 0.050 Uiso 1 1 calc R . . C20 C 0.9740(4) 0.1923(3) 0.64405(16) 0.0428(8) Uani 1 1 d . . . H20 H 0.9735 0.1748 0.6975 0.051 Uiso 1 1 calc R . . C21 C 1.0360(4) 0.1198(2) 0.59503(15) 0.0403(7) Uani 1 1 d . . . H21 H 1.0763 0.0520 0.6145 0.048 Uiso 1 1 calc R . . C22 C 1.0398(4) 0.1458(2) 0.51689(15) 0.0335(6) Uani 1 1 d . . . H22 H 1.0835 0.0956 0.4835 0.040 Uiso 1 1 calc R . . O1 O 0.9993(2) 0.19202(12) 0.35453(9) 0.0252(4) Uani 1 1 d . . . Br1 Br 1.02007(4) 0.70795(2) 0.049923(16) 0.03870(12) 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 C1 0.0244(14) 0.0227(14) 0.0302(14) 0.0027(10) -0.0033(11) -0.0038(12) C2 0.0228(14) 0.0241(14) 0.0270(13) -0.0017(10) 0.0039(10) 0.0003(11) C3 0.0203(14) 0.0199(13) 0.0298(13) -0.0047(10) 0.0025(10) 0.0016(11) C4 0.0195(13) 0.0223(14) 0.0283(13) -0.0031(10) -0.0003(11) -0.0017(11) C5 0.0270(15) 0.0264(15) 0.0314(14) -0.0036(11) 0.0057(11) 0.0047(12) C6 0.0277(15) 0.0224(14) 0.0361(15) -0.0045(11) 0.0024(12) 0.0057(12) C7 0.0213(14) 0.0228(14) 0.0260(13) -0.0014(10) 0.0048(10) 0.0014(11) C8 0.0198(14) 0.0267(14) 0.0231(13) 0.0009(10) 0.0042(10) 0.0000(11) C9 0.0194(13) 0.0219(13) 0.0239(12) 0.0017(10) 0.0071(10) -0.0002(11) C10 0.0215(13) 0.0201(13) 0.0279(13) 0.0010(10) 0.0027(10) 0.0014(11) C11 0.0330(16) 0.0279(15) 0.0223(13) 0.0009(10) 0.0013(11) -0.0022(12) C12 0.0419(17) 0.0232(14) 0.0276(14) -0.0033(11) 0.0101(12) -0.0014(13) C13 0.0396(17) 0.0227(14) 0.0347(15) 0.0030(11) 0.0082(13) 0.0085(13) C14 0.0269(14) 0.0261(14) 0.0254(13) 0.0028(10) 0.0014(11) 0.0045(12) C15 0.0278(15) 0.0252(14) 0.0307(14) -0.0042(11) 0.0056(11) -0.0003(12) C16 0.0245(15) 0.0342(16) 0.0256(14) -0.0085(11) 0.0059(11) -0.0017(12) C17 0.0214(14) 0.0351(16) 0.0252(13) -0.0014(12) 0.0017(11) -0.0101(12) C18 0.0283(16) 0.0444(17) 0.0301(14) -0.0071(12) 0.0071(12) -0.0052(13) C19 0.0337(17) 0.062(2) 0.0316(15) -0.0135(14) 0.0104(13) -0.0158(16) C20 0.0389(18) 0.064(2) 0.0257(15) 0.0025(14) 0.0069(13) -0.0234(17) C21 0.0425(18) 0.0442(18) 0.0328(16) 0.0061(13) 0.0009(13) -0.0179(15) C22 0.0335(16) 0.0367(17) 0.0302(14) -0.0015(12) 0.0047(12) -0.0092(14) O1 0.0294(10) 0.0238(10) 0.0224(9) 0.0002(7) 0.0035(7) -0.0004(8) Br1 0.0477(2) 0.02337(18) 0.04541(19) 0.00778(11) 0.00815(14) 0.00349(13) _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 C1 C2 1.379(3) . ? C1 C6 1.385(3) . ? C1 Br1 1.899(2) . ? C2 C3 1.382(3) . ? C2 H2 0.9500 . ? C3 C4 1.402(3) . ? C3 H3 0.9500 . ? C4 C5 1.399(3) . ? C4 C7 1.474(3) . ? C5 C6 1.377(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.374(4) . ? C7 C15 1.432(3) . ? C8 O1 1.384(3) . ? C8 C9 1.468(3) . ? C9 C14 1.395(3) . ? C9 C10 1.400(3) . ? C10 C11 1.381(3) . ? C10 H10 0.9500 . ? C11 C12 1.391(3) . ? C11 H11 0.9500 . ? C12 C13 1.384(3) . ? C12 H12 0.9500 . ? C13 C14 1.384(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.346(4) . ? C15 H15 0.9500 . ? C16 O1 1.383(3) . ? C16 C17 1.459(4) . ? C17 C22 1.386(4) . ? C17 C18 1.405(4) . ? C18 C19 1.388(4) . ? C18 H18 0.9500 . ? C19 C20 1.380(4) . ? C19 H19 0.9500 . ? C20 C21 1.377(4) . ? C20 H20 0.9500 . ? C21 C22 1.394(4) . ? C21 H21 0.9500 . ? C22 H22 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 C2 C1 C6 120.8(2) . . ? C2 C1 Br1 119.44(18) . . ? C6 C1 Br1 119.75(19) . . ? C1 C2 C3 119.5(2) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 121.3(2) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 117.3(2) . . ? C5 C4 C7 120.0(2) . . ? C3 C4 C7 122.5(2) . . ? C6 C5 C4 121.8(2) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C5 C6 C1 119.2(2) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? C8 C7 C15 105.4(2) . . ? C8 C7 C4 129.9(2) . . ? C15 C7 C4 124.5(2) . . ? C7 C8 O1 109.6(2) . . ? C7 C8 C9 136.1(2) . . ? O1 C8 C9 114.0(2) . . ? C14 C9 C10 118.7(2) . . ? C14 C9 C8 120.3(2) . . ? C10 C9 C8 120.9(2) . . ? C11 C10 C9 120.3(2) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 120.6(2) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 119.5(2) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C14 C13 C12 120.2(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C9 120.8(2) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? C16 C15 C7 108.6(2) . . ? C16 C15 H15 125.7 . . ? C7 C15 H15 125.7 . . ? C15 C16 O1 109.0(2) . . ? C15 C16 C17 134.4(2) . . ? O1 C16 C17 116.6(2) . . ? C22 C17 C18 118.8(2) . . ? C22 C17 C16 122.2(2) . . ? C18 C17 C16 119.1(2) . . ? C19 C18 C17 120.2(3) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 120.2(3) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 120.1(3) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 120.2(3) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C17 C22 C21 120.5(3) . . ? C17 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C16 O1 C8 107.29(18) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.337 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.063 # Attachment 'a11023.cif' data_a11023 _database_code_depnum_ccdc_archive 'CCDC 792218' #TrackingRef 'a11023.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H14 Br N O' _chemical_formula_sum 'C23 H14 Br N O' _chemical_formula_weight 400.26 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.4569(2) _cell_length_b 21.6536(7) _cell_length_c 10.4183(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.158(2) _cell_angle_gamma 90.00 _cell_volume 1779.21(9) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 2.321 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4570 _exptl_absorpt_correction_T_max 0.6414 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10771 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3133 _reflns_number_gt 2576 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0292P)^2^+0.5894P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3133 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0666 _refine_ls_wR_factor_gt 0.0627 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 -0.27852(3) 0.019229(12) 0.52292(3) 0.04554(10) Uani 1 1 d . . . C1 C -0.1432(3) 0.08450(10) 0.4955(2) 0.0306(5) Uani 1 1 d . . . C2 C -0.2006(3) 0.11247(11) 0.3669(2) 0.0365(5) Uani 1 1 d . . . H2 H -0.3018 0.0984 0.2973 0.044 Uiso 1 1 calc R . . C3 C -0.1102(3) 0.16068(11) 0.3408(3) 0.0400(6) Uani 1 1 d . . . H3 H -0.1480 0.1797 0.2527 0.048 Uiso 1 1 calc R . . C4 C 0.0359(3) 0.18114(11) 0.4435(3) 0.0386(6) Uani 1 1 d . . . H4 H 0.0986 0.2143 0.4257 0.046 Uiso 1 1 calc R . . C5 C 0.0910(3) 0.15379(10) 0.5714(2) 0.0343(5) Uani 1 1 d . . . H5 H 0.1906 0.1689 0.6412 0.041 Uiso 1 1 calc R . . C6 C 0.0031(3) 0.10404(10) 0.6009(2) 0.0284(5) Uani 1 1 d . . . C7 C 0.0717(3) 0.07609(10) 0.7382(2) 0.0287(5) Uani 1 1 d . . . C8 C 0.0935(3) 0.01817(10) 0.7892(2) 0.0306(5) Uani 1 1 d . . . H8 H 0.0504 -0.0185 0.7385 0.037 Uiso 1 1 calc R . . C9 C 0.1927(3) 0.02171(10) 0.9328(2) 0.0276(5) Uani 1 1 d . . . C10 C 0.2224(3) 0.08316(10) 0.9621(2) 0.0289(5) Uani 1 1 d . . . C11 C 0.2993(3) 0.12070(10) 1.0868(2) 0.0302(5) Uani 1 1 d . . . C12 C 0.3666(3) 0.17850(11) 1.0792(3) 0.0412(6) Uani 1 1 d . . . H12 H 0.3671 0.1932 0.9935 0.049 Uiso 1 1 calc R . . C13 C 0.4330(3) 0.21476(12) 1.1958(3) 0.0491(7) Uani 1 1 d . . . H13 H 0.4779 0.2543 1.1892 0.059 Uiso 1 1 calc R . . C14 C 0.4345(3) 0.19411(11) 1.3213(3) 0.0440(6) Uani 1 1 d . . . H14 H 0.4815 0.2190 1.4013 0.053 Uiso 1 1 calc R . . C15 C 0.3672(3) 0.13689(11) 1.3296(2) 0.0378(6) Uani 1 1 d . . . H15 H 0.3675 0.1224 1.4158 0.045 Uiso 1 1 calc R . . C16 C 0.2992(3) 0.10054(10) 1.2138(2) 0.0319(5) Uani 1 1 d . . . H16 H 0.2519 0.0614 1.2207 0.038 Uiso 1 1 calc R . . C17 C 0.2580(3) -0.03213(10) 1.0236(2) 0.0274(5) Uani 1 1 d . . . C18 C 0.4165(3) -0.03119(10) 1.1300(2) 0.0311(5) Uani 1 1 d . . . H18 H 0.4839 0.0051 1.1453 0.037 Uiso 1 1 calc R . . C19 C 0.4766(3) -0.08185(10) 1.2128(2) 0.0314(5) Uani 1 1 d . . . H19 H 0.5839 -0.0801 1.2854 0.038 Uiso 1 1 calc R . . C20 C 0.3804(3) -0.13559(10) 1.1904(2) 0.0295(5) Uani 1 1 d . . . C21 C 0.4461(3) -0.18858(11) 1.2783(2) 0.0343(5) Uani 1 1 d . . . C22 C 0.2236(3) -0.13821(10) 1.0827(2) 0.0336(5) Uani 1 1 d . . . H22 H 0.1580 -0.1750 1.0661 0.040 Uiso 1 1 calc R . . C23 C 0.1645(3) -0.08701(10) 1.0005(2) 0.0319(5) Uani 1 1 d . . . H23 H 0.0582 -0.0891 0.9267 0.038 Uiso 1 1 calc R . . N1 N 0.5015(3) -0.22990(10) 1.3476(2) 0.0463(5) Uani 1 1 d . . . O1 O 0.15074(18) 0.11704(7) 0.84335(15) 0.0304(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 Br1 0.04487(16) 0.04520(17) 0.03955(17) 0.00438(12) 0.00680(12) -0.01376(12) C1 0.0350(12) 0.0283(12) 0.0304(13) -0.0001(10) 0.0141(11) 0.0013(10) C2 0.0405(13) 0.0369(13) 0.0298(14) 0.0002(11) 0.0099(11) 0.0040(11) C3 0.0509(16) 0.0397(14) 0.0321(14) 0.0085(11) 0.0185(13) 0.0090(12) C4 0.0412(14) 0.0341(13) 0.0450(16) 0.0090(12) 0.0208(13) 0.0034(11) C5 0.0320(13) 0.0321(13) 0.0385(14) 0.0032(11) 0.0123(11) 0.0021(10) C6 0.0315(12) 0.0271(11) 0.0280(13) 0.0001(10) 0.0124(10) 0.0054(9) C7 0.0286(11) 0.0310(12) 0.0268(12) -0.0025(10) 0.0103(10) -0.0005(9) C8 0.0302(12) 0.0286(12) 0.0328(13) -0.0024(10) 0.0112(10) 0.0009(10) C9 0.0249(11) 0.0301(12) 0.0285(13) 0.0015(10) 0.0103(10) 0.0006(9) C10 0.0275(11) 0.0321(13) 0.0286(13) 0.0033(10) 0.0121(10) 0.0003(9) C11 0.0309(12) 0.0314(12) 0.0288(13) -0.0022(10) 0.0112(11) -0.0010(10) C12 0.0567(16) 0.0374(14) 0.0320(14) -0.0019(11) 0.0189(12) -0.0097(12) C13 0.0670(18) 0.0321(14) 0.0474(17) -0.0044(12) 0.0198(15) -0.0122(13) C14 0.0533(16) 0.0386(14) 0.0360(15) -0.0105(12) 0.0112(13) 0.0014(12) C15 0.0425(14) 0.0407(14) 0.0308(14) 0.0007(11) 0.0141(12) 0.0075(11) C16 0.0336(12) 0.0314(12) 0.0315(13) 0.0003(10) 0.0126(11) 0.0012(10) C17 0.0279(12) 0.0284(12) 0.0294(12) -0.0007(9) 0.0147(11) 0.0011(9) C18 0.0267(12) 0.0281(12) 0.0367(14) -0.0051(10) 0.0091(11) -0.0026(9) C19 0.0266(11) 0.0308(13) 0.0312(13) -0.0059(10) 0.0038(10) 0.0007(10) C20 0.0323(12) 0.0289(12) 0.0257(12) -0.0016(10) 0.0085(10) 0.0029(9) C21 0.0388(13) 0.0314(13) 0.0302(14) -0.0053(11) 0.0093(11) -0.0004(11) C22 0.0327(13) 0.0305(13) 0.0346(14) -0.0008(11) 0.0085(11) -0.0068(10) C23 0.0255(11) 0.0365(13) 0.0277(13) -0.0012(10) 0.0024(10) -0.0027(10) N1 0.0599(14) 0.0354(12) 0.0346(13) -0.0003(11) 0.0064(11) 0.0048(11) O1 0.0350(8) 0.0279(8) 0.0280(9) 0.0004(7) 0.0110(7) 0.0000(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 Br1 C1 1.904(2) . ? C1 C2 1.388(3) . ? C1 C6 1.392(3) . ? C2 C3 1.378(3) . ? C2 H2 0.9500 . ? C3 C4 1.384(3) . ? C3 H3 0.9500 . ? C4 C5 1.377(3) . ? C4 H4 0.9500 . ? C5 C6 1.404(3) . ? C5 H5 0.9500 . ? C6 C7 1.466(3) . ? C7 C8 1.348(3) . ? C7 O1 1.380(3) . ? C8 C9 1.430(3) . ? C8 H8 0.9500 . ? C9 C10 1.368(3) . ? C9 C17 1.477(3) . ? C10 O1 1.377(3) . ? C10 C11 1.470(3) . ? C11 C12 1.389(3) . ? C11 C16 1.394(3) . ? C12 C13 1.384(3) . ? C12 H12 0.9500 . ? C13 C14 1.378(3) . ? C13 H13 0.9500 . ? C14 C15 1.379(3) . ? C14 H14 0.9500 . ? C15 C16 1.380(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.397(3) . ? C17 C23 1.399(3) . ? C18 C19 1.375(3) . ? C18 H18 0.9500 . ? C19 C20 1.390(3) . ? C19 H19 0.9500 . ? C20 C22 1.395(3) . ? C20 C21 1.448(3) . ? C21 N1 1.139(3) . ? C22 C23 1.380(3) . ? C22 H22 0.9500 . ? C23 H23 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 C2 C1 C6 122.1(2) . . ? C2 C1 Br1 116.67(17) . . ? C6 C1 Br1 121.25(16) . . ? C3 C2 C1 119.7(2) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 119.6(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 121.4(2) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 116.8(2) . . ? C1 C6 C7 124.79(19) . . ? C5 C6 C7 118.4(2) . . ? C8 C7 O1 109.08(19) . . ? C8 C7 C6 135.9(2) . . ? O1 C7 C6 114.63(18) . . ? C7 C8 C9 107.9(2) . . ? C7 C8 H8 126.0 . . ? C9 C8 H8 126.0 . . ? C10 C9 C8 106.06(19) . . ? C10 C9 C17 129.0(2) . . ? C8 C9 C17 124.81(19) . . ? C9 C10 O1 109.40(19) . . ? C9 C10 C11 136.2(2) . . ? O1 C10 C11 114.22(18) . . ? C12 C11 C16 118.5(2) . . ? C12 C11 C10 120.5(2) . . ? C16 C11 C10 120.93(19) . . ? C13 C12 C11 120.4(2) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 120.7(2) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 119.2(2) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C16 C15 C14 120.6(2) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C11 120.6(2) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C18 C17 C23 118.0(2) . . ? C18 C17 C9 121.75(19) . . ? C23 C17 C9 120.2(2) . . ? C19 C18 C17 121.2(2) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C18 C19 C20 120.1(2) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C20 C22 119.8(2) . . ? C19 C20 C21 119.3(2) . . ? C22 C20 C21 120.9(2) . . ? N1 C21 C20 178.4(3) . . ? C23 C22 C20 119.5(2) . . ? C23 C22 H22 120.2 . . ? C20 C22 H22 120.2 . . ? C22 C23 C17 121.3(2) . . ? C22 C23 H23 119.3 . . ? C17 C23 H23 119.3 . . ? C10 O1 C7 107.52(16) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.252 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.046