# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Alex Slawin' _publ_contact_author_email amzs@st-andrews.ac.uk loop_ _publ_author_name 'Mathilde Lachia' 'Cyril Poriel' 'Alexandra M. Z. Slawin' 'Christopher J. Moody' data_8b _database_code_depnum_ccdc_archive 'CCDC 609781' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H21 Br N2 O3.(C H Cl3)0.5' _chemical_formula_sum 'C21.50 H21.50 Br Cl1.50 N2 O3' _chemical_formula_weight 488.99 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 9.64370(19) _cell_length_b 12.4445(12) _cell_length_c 18.3737(17) _cell_angle_alpha 90.00 _cell_angle_beta 102.099(3) _cell_angle_gamma 90.00 _cell_volume 2156.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7230 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 60.35 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 996 _exptl_absorpt_coefficient_mu 4.520 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3940 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28203 _diffrn_reflns_av_R_equivalents 0.1652 _diffrn_reflns_av_sigmaI/netI 0.1397 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 67.98 _reflns_number_total 7217 _reflns_number_gt 4900 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0122P)^2^+14.1128P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 7217 _refine_ls_number_parameters 532 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1471 _refine_ls_R_factor_gt 0.0858 _refine_ls_wR_factor_ref 0.1574 _refine_ls_wR_factor_gt 0.1330 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.004 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 0.4697(11) 0.9729(10) 0.0013(6) 0.025(3) Uani 1 1 d . . . C2 C 0.4868(11) 0.8479(9) -0.0061(6) 0.021(2) Uani 1 1 d . . . O2 O 0.5391(8) 0.8051(6) -0.0521(4) 0.0346(19) Uani 1 1 d . . . N3 N 0.4388(9) 0.8011(6) 0.0517(5) 0.024(2) Uani 1 1 d D . . H3N H 0.419(10) 0.7239(16) 0.054(5) 0.04(3) Uiso 1 1 d D . . C4 C 0.3770(12) 0.8783(9) 0.0900(6) 0.026(3) Uani 1 1 d . . . C5 C 0.3044(11) 0.8615(9) 0.1469(5) 0.027(3) Uani 1 1 d . . . Br5 Br 0.28028(13) 0.7203(3) 0.18331(6) 0.0360(3) Uani 1 1 d . . . C6 C 0.2508(11) 0.9495(10) 0.1790(6) 0.029(3) Uani 1 1 d . . . H6A H 0.2049 0.9393 0.2194 0.035 Uiso 1 1 calc R . . C7 C 0.2643(12) 1.0511(11) 0.1520(6) 0.034(3) Uani 1 1 d . . . H7A H 0.2276 1.1112 0.1737 0.040 Uiso 1 1 calc R . . C8 C 0.3315(11) 1.0657(10) 0.0929(6) 0.030(3) Uani 1 1 d . . . H8A H 0.3372 1.1355 0.0728 0.036 Uiso 1 1 calc R . . C9 C 0.3891(11) 0.9807(10) 0.0640(5) 0.024(3) Uani 1 1 d . . . C10 C 0.3889(11) 1.0264(8) -0.0717(5) 0.022(2) Uani 1 1 d . . . O10 O 0.4434(7) 1.0981(6) -0.1022(4) 0.0287(18) Uani 1 1 d . . . N11 N 0.2540(9) 0.9945(7) -0.0999(4) 0.025(2) Uani 1 1 d . . . C12 C 0.1674(11) 1.0541(9) -0.1645(6) 0.025(2) Uani 1 1 d . . . H12A H 0.2145 1.0482 -0.2079 0.030 Uiso 1 1 calc R . . C13 C 0.0241(13) 0.9922(10) -0.1824(6) 0.035(3) Uani 1 1 d . . . H13A H -0.0501 1.0314 -0.1633 0.042 Uiso 1 1 calc R . . H13B H -0.0082 0.9817 -0.2368 0.042 Uiso 1 1 calc R . . C14 C 0.0572(12) 0.8854(11) -0.1430(6) 0.042(3) Uani 1 1 d . . . H14A H -0.0286 0.8552 -0.1290 0.050 Uiso 1 1 calc R . . H14B H 0.0932 0.8332 -0.1752 0.050 Uiso 1 1 calc R . . C15 C 0.1703(11) 0.9108(10) -0.0740(6) 0.035(3) Uani 1 1 d . . . H15A H 0.1272 0.9371 -0.0329 0.042 Uiso 1 1 calc R . . H15B H 0.2290 0.8467 -0.0568 0.042 Uiso 1 1 calc R . . C16 C 0.1487(11) 1.1722(9) -0.1476(6) 0.029(3) Uani 1 1 d . . . H16A H 0.2409 1.2100 -0.1405 0.034 Uiso 1 1 calc R . . H16B H 0.0820 1.2066 -0.1894 0.034 Uiso 1 1 calc R . . O17 O 0.0952(9) 1.1779(7) -0.0826(4) 0.042(2) Uani 1 1 d . . . C18 C 0.0853(15) 1.2876(12) -0.0583(8) 0.059(4) Uani 1 1 d . . . H18A H 0.0475 1.2883 -0.0128 0.089 Uiso 1 1 calc R . . H18B H 0.0219 1.3282 -0.0973 0.089 Uiso 1 1 calc R . . H18C H 0.1797 1.3205 -0.0483 0.089 Uiso 1 1 calc R . . C19 C 0.6199(12) 1.0186(9) 0.0243(6) 0.026(2) Uani 1 1 d . . . C20 C 0.6715(13) 1.0648(9) 0.0918(6) 0.032(3) Uani 1 1 d . . . H20A H 0.6109 1.0721 0.1262 0.039 Uiso 1 1 calc R . . C21 C 0.8089(12) 1.1012(10) 0.1115(7) 0.040(3) Uani 1 1 d . . . H21A H 0.8432 1.1284 0.1602 0.048 Uiso 1 1 calc R . . C22 C 0.8959(13) 1.0988(11) 0.0627(8) 0.046(4) Uani 1 1 d . . . H22A H 0.9900 1.1257 0.0761 0.055 Uiso 1 1 calc R . . C23 C 0.8450(12) 1.0564(10) -0.0070(7) 0.040(3) Uani 1 1 d . . . H23A H 0.9043 1.0556 -0.0422 0.048 Uiso 1 1 calc R . . C24 C 0.7097(11) 1.0151(9) -0.0266(6) 0.032(3) Uani 1 1 d . . . H24A H 0.6774 0.9843 -0.0745 0.038 Uiso 1 1 calc R . . C31 C 0.4765(10) 0.9037(9) 0.4828(5) 0.022(3) Uani 1 1 d . . . C32 C 0.4995(11) 0.7783(9) 0.4957(6) 0.024(2) Uani 1 1 d . . . O32 O 0.6042(8) 0.7364(7) 0.5314(4) 0.0321(19) Uani 1 1 d . . . N33 N 0.3734(8) 0.7307(5) 0.4620(4) 0.0250(19) Uani 1 1 d D . . H33N H 0.367(10) 0.6530(14) 0.469(5) 0.04(3) Uiso 1 1 d D . . C34 C 0.2811(11) 0.8034(9) 0.4225(6) 0.025(2) Uani 1 1 d . . . C35 C 0.1469(11) 0.7852(9) 0.3778(6) 0.027(3) Uani 1 1 d . . . Br35 Br 0.07760(14) 0.6424(3) 0.36130(7) 0.0407(3) Uani 1 1 d . . . C36 C 0.0697(11) 0.8695(9) 0.3402(6) 0.026(3) Uani 1 1 d . . . H36A H -0.0190 0.8565 0.3075 0.031 Uiso 1 1 calc R . . C37 C 0.1225(11) 0.9721(10) 0.3508(6) 0.032(3) Uani 1 1 d . . . H37A H 0.0668 1.0305 0.3275 0.039 Uiso 1 1 calc R . . C38 C 0.2574(12) 0.9926(9) 0.3954(6) 0.031(3) Uani 1 1 d . . . H38A H 0.2955 1.0633 0.4003 0.037 Uiso 1 1 calc R . . C39 C 0.3325(11) 0.9072(8) 0.4316(5) 0.022(2) Uani 1 1 d . . . C40 C 0.5888(12) 0.9591(9) 0.4470(6) 0.027(3) Uani 1 1 d . . . O40 O 0.6597(8) 1.0363(7) 0.4780(4) 0.0322(19) Uani 1 1 d . . . N41 N 0.6041(9) 0.9238(8) 0.3804(5) 0.027(2) Uani 1 1 d . . . C42 C 0.6835(12) 0.9893(9) 0.3342(6) 0.024(3) Uani 1 1 d . . . H42A H 0.7843 0.9992 0.3608 0.029 Uiso 1 1 calc R . . C43 C 0.6756(11) 0.9226(10) 0.2643(6) 0.030(3) Uani 1 1 d . . . H43A H 0.7645 0.9286 0.2457 0.036 Uiso 1 1 calc R . . H43B H 0.5951 0.9458 0.2246 0.036 Uiso 1 1 calc R . . C44 C 0.6534(12) 0.8064(10) 0.2897(6) 0.033(3) Uani 1 1 d . . . H44A H 0.6093 0.7608 0.2469 0.039 Uiso 1 1 calc R . . H44B H 0.7445 0.7737 0.3148 0.039 Uiso 1 1 calc R . . C45 C 0.5562(13) 0.8203(10) 0.3428(7) 0.038(3) Uani 1 1 d . . . H45A H 0.4560 0.8245 0.3159 0.046 Uiso 1 1 calc R . . H45B H 0.5667 0.7604 0.3790 0.046 Uiso 1 1 calc R . . C46 C 0.6091(12) 1.0986(9) 0.3177(6) 0.032(3) Uani 1 1 d . . . H46A H 0.5065 1.0886 0.2972 0.039 Uiso 1 1 calc R . . H46B H 0.6208 1.1422 0.3636 0.039 Uiso 1 1 calc R . . O47 O 0.6751(9) 1.1498(7) 0.2647(4) 0.047(2) Uani 1 1 d . . . C48 C 0.6165(16) 1.2536(10) 0.2485(8) 0.059(4) Uani 1 1 d . . . H48A H 0.6627 1.2888 0.2122 0.088 Uiso 1 1 calc R . . H48B H 0.6316 1.2963 0.2942 0.088 Uiso 1 1 calc R . . H48C H 0.5145 1.2473 0.2277 0.088 Uiso 1 1 calc R . . C49 C 0.4720(13) 0.9501(9) 0.5602(6) 0.032(3) Uani 1 1 d . . . C50 C 0.3530(12) 0.9916(9) 0.5784(7) 0.031(3) Uani 1 1 d . . . H50A H 0.2684 0.9966 0.5412 0.037 Uiso 1 1 calc R . . C51 C 0.3523(15) 1.0271(11) 0.6511(7) 0.050(4) Uani 1 1 d . . . H51A H 0.2672 1.0537 0.6627 0.060 Uiso 1 1 calc R . . C52 C 0.4747(14) 1.0232(11) 0.7052(7) 0.047(3) Uani 1 1 d . . . H52A H 0.4743 1.0470 0.7543 0.056 Uiso 1 1 calc R . . C53 C 0.5984(14) 0.9846(10) 0.6879(6) 0.042(3) Uani 1 1 d . . . H53A H 0.6836 0.9829 0.7249 0.050 Uiso 1 1 calc R . . C54 C 0.5977(12) 0.9483(10) 0.6167(6) 0.036(3) Uani 1 1 d . . . H54A H 0.6830 0.9217 0.6054 0.043 Uiso 1 1 calc R . . C61 C -0.0592(13) 0.7697(11) 0.5702(7) 0.047(3) Uani 1 1 d . . . H61A H -0.1556 0.7395 0.5498 0.056 Uiso 1 1 calc R . . Cl1 Cl -0.0417(5) 0.7889(5) 0.6666(2) 0.0937(16) Uani 1 1 d . . . Cl2 Cl 0.0658(5) 0.6772(4) 0.5542(2) 0.0730(12) Uani 1 1 d . . . Cl3 Cl -0.0434(4) 0.8902(4) 0.5245(3) 0.0840(14) 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 0.038(7) 0.022(6) 0.018(5) -0.006(4) 0.011(5) -0.001(6) C2 0.019(6) 0.017(6) 0.024(6) -0.006(5) -0.003(5) -0.004(5) O2 0.049(5) 0.022(5) 0.036(4) -0.008(4) 0.018(4) 0.006(4) N3 0.025(5) 0.021(6) 0.028(5) 0.000(4) 0.007(4) -0.001(4) C4 0.038(7) 0.014(6) 0.022(6) 0.008(4) -0.001(5) -0.004(5) C5 0.032(6) 0.030(7) 0.015(5) 0.008(5) -0.003(5) -0.004(5) Br5 0.0410(7) 0.0291(7) 0.0384(7) 0.0071(6) 0.0098(6) -0.0077(7) C6 0.032(7) 0.036(8) 0.023(6) 0.000(5) 0.014(5) -0.001(6) C7 0.035(7) 0.044(8) 0.016(6) -0.014(6) -0.008(5) 0.018(6) C8 0.034(7) 0.027(7) 0.027(6) -0.005(5) 0.001(5) 0.001(6) C9 0.020(6) 0.035(7) 0.015(5) 0.004(5) 0.001(4) 0.009(5) C10 0.031(6) 0.008(5) 0.025(6) 0.000(4) 0.004(5) -0.006(5) O10 0.031(4) 0.017(4) 0.036(4) 0.004(3) 0.003(3) -0.002(3) N11 0.028(5) 0.018(5) 0.027(5) 0.001(4) 0.000(4) -0.001(4) C12 0.027(6) 0.022(6) 0.025(6) -0.003(5) 0.000(5) 0.006(5) C13 0.048(8) 0.028(7) 0.023(6) -0.008(5) -0.005(5) 0.001(6) C14 0.033(7) 0.049(9) 0.038(7) 0.005(6) -0.005(6) -0.012(7) C15 0.026(6) 0.040(8) 0.041(7) 0.004(6) 0.011(6) -0.001(6) C16 0.021(6) 0.030(7) 0.037(6) 0.008(5) 0.008(5) 0.001(5) O17 0.051(5) 0.029(5) 0.053(5) -0.008(4) 0.023(4) -0.007(4) C18 0.063(10) 0.046(10) 0.071(10) -0.017(8) 0.016(8) -0.005(8) C19 0.034(7) 0.015(6) 0.026(6) 0.003(5) 0.002(5) -0.002(5) C20 0.043(7) 0.023(7) 0.030(6) -0.005(5) 0.006(5) 0.004(6) C21 0.031(7) 0.043(9) 0.042(7) 0.014(6) 0.000(6) -0.003(6) C22 0.025(7) 0.044(9) 0.064(9) 0.020(7) -0.002(7) -0.002(6) C23 0.034(7) 0.028(7) 0.061(9) 0.029(7) 0.020(7) 0.006(6) C24 0.029(6) 0.031(7) 0.034(6) -0.010(5) 0.002(5) 0.008(5) C31 0.010(5) 0.018(6) 0.030(7) -0.009(5) -0.010(5) 0.003(5) C32 0.018(5) 0.029(7) 0.023(6) -0.005(5) 0.002(5) 0.002(5) O32 0.036(4) 0.020(5) 0.037(4) 0.007(4) -0.001(4) 0.002(4) N33 0.027(5) 0.010(5) 0.036(5) 0.006(4) 0.003(4) -0.004(4) C34 0.026(6) 0.017(6) 0.033(6) -0.001(5) 0.012(5) 0.005(5) C35 0.017(6) 0.026(7) 0.039(7) -0.005(5) 0.010(5) -0.004(5) Br35 0.0394(7) 0.0306(8) 0.0469(8) -0.0066(7) -0.0032(6) -0.0110(7) C36 0.029(6) 0.020(7) 0.028(6) -0.001(5) 0.005(5) 0.005(5) C37 0.025(6) 0.038(8) 0.032(7) 0.004(6) 0.002(5) 0.014(6) C38 0.041(7) 0.025(7) 0.030(6) 0.002(5) 0.015(5) -0.001(6) C39 0.027(6) 0.015(6) 0.023(6) 0.010(4) 0.007(5) 0.004(5) C40 0.032(7) 0.017(7) 0.034(7) 0.010(5) 0.011(5) 0.017(5) O40 0.039(5) 0.018(4) 0.040(5) -0.011(4) 0.010(4) -0.010(4) N41 0.029(5) 0.024(6) 0.025(5) -0.009(4) -0.001(4) -0.001(4) C42 0.025(6) 0.021(7) 0.029(6) 0.000(5) 0.009(5) 0.002(5) C43 0.019(6) 0.042(8) 0.028(6) -0.005(6) 0.006(5) 0.000(5) C44 0.029(6) 0.029(7) 0.040(7) 0.003(6) 0.007(5) -0.009(6) C45 0.043(8) 0.031(8) 0.049(8) -0.009(6) 0.027(6) -0.010(6) C46 0.034(7) 0.029(7) 0.032(6) 0.010(5) 0.002(5) 0.004(5) O47 0.067(5) 0.028(5) 0.051(5) 0.013(5) 0.027(4) 0.009(5) C48 0.089(11) 0.019(8) 0.070(10) 0.018(7) 0.020(9) -0.009(7) C49 0.044(8) 0.012(6) 0.037(7) 0.013(5) 0.006(6) 0.003(6) C50 0.025(6) 0.024(7) 0.046(7) -0.001(6) 0.011(5) 0.003(5) C51 0.057(9) 0.040(9) 0.055(9) -0.025(7) 0.018(7) -0.016(7) C52 0.054(9) 0.042(8) 0.043(8) -0.022(6) 0.005(7) -0.024(7) C53 0.047(8) 0.042(8) 0.035(7) -0.017(6) 0.005(6) -0.011(7) C54 0.032(7) 0.030(7) 0.044(8) 0.004(6) 0.005(6) -0.001(6) C61 0.041(8) 0.046(9) 0.047(8) 0.002(6) -0.004(6) 0.002(7) Cl1 0.106(4) 0.114(4) 0.056(3) -0.028(3) 0.005(2) 0.034(3) Cl2 0.104(3) 0.051(3) 0.074(2) 0.0123(18) 0.041(2) 0.030(2) Cl3 0.072(3) 0.055(3) 0.128(4) 0.028(3) 0.028(3) 0.020(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C9 1.522(13) . ? C1 C19 1.530(15) . ? C1 C10 1.553(15) . ? C1 C2 1.573(15) . ? C2 O2 1.196(11) . ? C2 N3 1.373(13) . ? N3 C4 1.397(13) . ? N3 H3N 0.9800(11) . ? C4 C9 1.375(13) . ? C4 C5 1.391(14) . ? C5 C6 1.393(15) . ? C5 Br5 1.911(11) . ? C6 C7 1.375(16) . ? C6 H6A 0.9500 . ? C7 C8 1.387(15) . ? C7 H7A 0.9500 . ? C8 C9 1.354(14) . ? C8 H8A 0.9500 . ? C10 O10 1.229(11) . ? C10 N11 1.355(12) . ? N11 C15 1.458(13) . ? N11 C12 1.497(13) . ? C12 C16 1.521(15) . ? C12 C13 1.556(15) . ? C12 H12A 1.0000 . ? C13 C14 1.515(16) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.522(15) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O17 1.399(12) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? O17 C18 1.445(14) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.363(14) . ? C19 C24 1.403(14) . ? C20 C21 1.375(15) . ? C20 H20A 0.9500 . ? C21 C22 1.350(17) . ? C21 H21A 0.9500 . ? C22 C23 1.376(17) . ? C22 H22A 0.9500 . ? C23 C24 1.378(15) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C31 C39 1.506(13) . ? C31 C49 1.543(15) . ? C31 C40 1.543(15) . ? C31 C32 1.587(15) . ? C32 O32 1.201(11) . ? C32 N33 1.377(13) . ? N33 C34 1.366(13) . ? N33 H33N 0.9800(11) . ? C34 C39 1.381(14) . ? C34 C35 1.398(14) . ? C35 C36 1.383(14) . ? C35 Br35 1.900(11) . ? C36 C37 1.374(15) . ? C36 H36A 0.9500 . ? C37 C38 1.408(15) . ? C37 H37A 0.9500 . ? C38 C39 1.377(14) . ? C38 H38A 0.9500 . ? C40 O40 1.245(13) . ? C40 N41 1.337(12) . ? N41 C45 1.489(14) . ? N41 C42 1.497(13) . ? C42 C43 1.517(14) . ? C42 C46 1.539(14) . ? C42 H42A 1.0000 . ? C43 C44 1.548(15) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 C45 1.498(15) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 O47 1.420(13) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? O47 C48 1.417(14) . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C49 C50 1.363(15) . ? C49 C54 1.422(15) . ? C50 C51 1.407(15) . ? C50 H50A 0.9500 . ? C51 C52 1.376(18) . ? C51 H51A 0.9500 . ? C52 C53 1.383(17) . ? C52 H52A 0.9500 . ? C53 C54 1.382(15) . ? C53 H53A 0.9500 . ? C54 H54A 0.9500 . ? C61 Cl2 1.736(13) . ? C61 Cl3 1.740(13) . ? C61 Cl1 1.760(13) . ? C61 H61A 1.0000 . ? 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 C9 C1 C19 111.8(9) . . ? C9 C1 C10 112.5(9) . . ? C19 C1 C10 110.7(9) . . ? C9 C1 C2 102.0(9) . . ? C19 C1 C2 106.4(8) . . ? C10 C1 C2 113.0(8) . . ? O2 C2 N3 128.1(10) . . ? O2 C2 C1 124.6(9) . . ? N3 C2 C1 107.1(8) . . ? C2 N3 C4 110.2(8) . . ? C2 N3 H3N 123(6) . . ? C4 N3 H3N 124(6) . . ? C9 C4 C5 119.6(10) . . ? C9 C4 N3 112.7(9) . . ? C5 C4 N3 127.7(10) . . ? C6 C5 C4 119.3(10) . . ? C6 C5 Br5 119.4(8) . . ? C4 C5 Br5 121.2(9) . . ? C7 C6 C5 119.9(10) . . ? C7 C6 H6A 120.0 . . ? C5 C6 H6A 120.0 . . ? C6 C7 C8 119.9(11) . . ? C6 C7 H7A 120.1 . . ? C8 C7 H7A 120.1 . . ? C9 C8 C7 120.1(11) . . ? C9 C8 H8A 119.9 . . ? C7 C8 H8A 119.9 . . ? C8 C9 C4 121.1(9) . . ? C8 C9 C1 131.6(11) . . ? C4 C9 C1 107.3(9) . . ? O10 C10 N11 120.4(9) . . ? O10 C10 C1 121.4(9) . . ? N11 C10 C1 118.2(9) . . ? C10 N11 C15 129.6(9) . . ? C10 N11 C12 119.3(8) . . ? C15 N11 C12 111.0(8) . . ? N11 C12 C16 112.8(8) . . ? N11 C12 C13 104.2(8) . . ? C16 C12 C13 112.6(9) . . ? N11 C12 H12A 109.0 . . ? C16 C12 H12A 109.0 . . ? C13 C12 H12A 109.0 . . ? C14 C13 C12 104.1(9) . . ? C14 C13 H13A 110.9 . . ? C12 C13 H13A 110.9 . . ? C14 C13 H13B 110.9 . . ? C12 C13 H13B 110.9 . . ? H13A C13 H13B 108.9 . . ? C15 C14 C13 105.0(10) . . ? C15 C14 H14A 110.7 . . ? C13 C14 H14A 110.7 . . ? C15 C14 H14B 110.7 . . ? C13 C14 H14B 110.7 . . ? H14A C14 H14B 108.8 . . ? N11 C15 C14 103.0(9) . . ? N11 C15 H15A 111.2 . . ? C14 C15 H15A 111.2 . . ? N11 C15 H15B 111.2 . . ? C14 C15 H15B 111.2 . . ? H15A C15 H15B 109.1 . . ? O17 C16 C12 107.7(8) . . ? O17 C16 H16A 110.2 . . ? C12 C16 H16A 110.2 . . ? O17 C16 H16B 110.2 . . ? C12 C16 H16B 110.2 . . ? H16A C16 H16B 108.5 . . ? C16 O17 C18 111.8(9) . . ? O17 C18 H18A 109.5 . . ? O17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 117.5(10) . . ? C20 C19 C1 123.5(10) . . ? C24 C19 C1 119.0(9) . . ? C19 C20 C21 121.7(11) . . ? C19 C20 H20A 119.2 . . ? C21 C20 H20A 119.2 . . ? C22 C21 C20 121.2(12) . . ? C22 C21 H21A 119.4 . . ? C20 C21 H21A 119.4 . . ? C21 C22 C23 118.4(12) . . ? C21 C22 H22A 120.8 . . ? C23 C22 H22A 120.8 . . ? C22 C23 C24 121.4(11) . . ? C22 C23 H23A 119.3 . . ? C24 C23 H23A 119.3 . . ? C23 C24 C19 119.7(10) . . ? C23 C24 H24A 120.1 . . ? C19 C24 H24A 120.1 . . ? C39 C31 C49 111.4(9) . . ? C39 C31 C40 111.0(9) . . ? C49 C31 C40 112.5(9) . . ? C39 C31 C32 101.7(8) . . ? C49 C31 C32 105.1(8) . . ? C40 C31 C32 114.5(8) . . ? O32 C32 N33 128.4(11) . . ? O32 C32 C31 125.7(9) . . ? N33 C32 C31 105.8(9) . . ? C34 N33 C32 111.8(9) . . ? C34 N33 H33N 132(6) . . ? C32 N33 H33N 116(6) . . ? N33 C34 C39 112.1(9) . . ? N33 C34 C35 128.7(10) . . ? C39 C34 C35 119.1(10) . . ? C36 C35 C34 120.4(10) . . ? C36 C35 Br35 119.6(8) . . ? C34 C35 Br35 119.7(8) . . ? C37 C36 C35 119.3(10) . . ? C37 C36 H36A 120.4 . . ? C35 C36 H36A 120.4 . . ? C36 C37 C38 121.4(11) . . ? C36 C37 H37A 119.3 . . ? C38 C37 H37A 119.3 . . ? C39 C38 C37 118.0(11) . . ? C39 C38 H38A 121.0 . . ? C37 C38 H38A 121.0 . . ? C38 C39 C34 121.6(10) . . ? C38 C39 C31 130.3(10) . . ? C34 C39 C31 108.0(9) . . ? O40 C40 N41 121.1(10) . . ? O40 C40 C31 121.1(10) . . ? N41 C40 C31 117.7(10) . . ? C40 N41 C45 128.8(9) . . ? C40 N41 C42 120.5(8) . . ? C45 N41 C42 110.7(8) . . ? N41 C42 C43 104.0(8) . . ? N41 C42 C46 108.7(8) . . ? C43 C42 C46 112.2(9) . . ? N41 C42 H42A 110.6 . . ? C43 C42 H42A 110.6 . . ? C46 C42 H42A 110.6 . . ? C42 C43 C44 104.0(9) . . ? C42 C43 H43A 111.0 . . ? C44 C43 H43A 111.0 . . ? C42 C43 H43B 111.0 . . ? C44 C43 H43B 111.0 . . ? H43A C43 H43B 109.0 . . ? C45 C44 C43 103.5(9) . . ? C45 C44 H44A 111.1 . . ? C43 C44 H44A 111.1 . . ? C45 C44 H44B 111.1 . . ? C43 C44 H44B 111.1 . . ? H44A C44 H44B 109.0 . . ? N41 C45 C44 103.1(9) . . ? N41 C45 H45A 111.2 . . ? C44 C45 H45A 111.1 . . ? N41 C45 H45B 111.1 . . ? C44 C45 H45B 111.2 . . ? H45A C45 H45B 109.1 . . ? O47 C46 C42 105.9(9) . . ? O47 C46 H46A 110.6 . . ? C42 C46 H46A 110.5 . . ? O47 C46 H46B 110.6 . . ? C42 C46 H46B 110.6 . . ? H46A C46 H46B 108.7 . . ? C46 O47 C48 109.7(9) . . ? O47 C48 H48A 109.5 . . ? O47 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? O47 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C50 C49 C54 117.3(11) . . ? C50 C49 C31 123.8(10) . . ? C54 C49 C31 118.9(10) . . ? C49 C50 C51 121.6(12) . . ? C49 C50 H50A 119.2 . . ? C51 C50 H50A 119.2 . . ? C52 C51 C50 120.1(13) . . ? C52 C51 H51A 120.0 . . ? C50 C51 H51A 120.0 . . ? C51 C52 C53 119.8(12) . . ? C51 C52 H52A 120.1 . . ? C53 C52 H52A 120.1 . . ? C54 C53 C52 119.8(12) . . ? C54 C53 H53A 120.1 . . ? C52 C53 H53A 120.1 . . ? C53 C54 C49 121.4(11) . . ? C53 C54 H54A 119.3 . . ? C49 C54 H54A 119.3 . . ? Cl2 C61 Cl3 110.8(7) . . ? Cl2 C61 Cl1 109.7(7) . . ? Cl3 C61 Cl1 111.6(8) . . ? Cl2 C61 H61A 108.2 . . ? Cl3 C61 H61A 108.2 . . ? Cl1 C61 H61A 108.2 . . ? 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 C1 C2 O2 176.2(10) . . . . ? C19 C1 C2 O2 -66.6(12) . . . . ? C10 C1 C2 O2 55.1(13) . . . . ? C9 C1 C2 N3 -7.2(10) . . . . ? C19 C1 C2 N3 110.0(9) . . . . ? C10 C1 C2 N3 -128.3(9) . . . . ? O2 C2 N3 C4 -176.3(11) . . . . ? C1 C2 N3 C4 7.2(11) . . . . ? C2 N3 C4 C9 -4.3(12) . . . . ? C2 N3 C4 C5 173.3(10) . . . . ? C9 C4 C5 C6 -3.0(15) . . . . ? N3 C4 C5 C6 179.6(10) . . . . ? C9 C4 C5 Br5 178.3(8) . . . . ? N3 C4 C5 Br5 0.8(16) . . . . ? C4 C5 C6 C7 3.0(16) . . . . ? Br5 C5 C6 C7 -178.3(8) . . . . ? C5 C6 C7 C8 -0.1(17) . . . . ? C6 C7 C8 C9 -2.8(16) . . . . ? C7 C8 C9 C4 2.8(16) . . . . ? C7 C8 C9 C1 -178.9(11) . . . . ? C5 C4 C9 C8 0.1(16) . . . . ? N3 C4 C9 C8 177.9(9) . . . . ? C5 C4 C9 C1 -178.6(9) . . . . ? N3 C4 C9 C1 -0.8(12) . . . . ? C19 C1 C9 C8 72.9(15) . . . . ? C10 C1 C9 C8 -52.4(16) . . . . ? C2 C1 C9 C8 -173.8(11) . . . . ? C19 C1 C9 C4 -108.6(11) . . . . ? C10 C1 C9 C4 126.1(10) . . . . ? C2 C1 C9 C4 4.7(11) . . . . ? C9 C1 C10 O10 123.4(11) . . . . ? C19 C1 C10 O10 -2.5(13) . . . . ? C2 C1 C10 O10 -121.7(10) . . . . ? C9 C1 C10 N11 -54.2(13) . . . . ? C19 C1 C10 N11 179.8(9) . . . . ? C2 C1 C10 N11 60.6(12) . . . . ? O10 C10 N11 C15 178.7(10) . . . . ? C1 C10 N11 C15 -3.6(16) . . . . ? O10 C10 N11 C12 -5.4(14) . . . . ? C1 C10 N11 C12 172.3(9) . . . . ? C10 N11 C12 C16 -59.8(12) . . . . ? C15 N11 C12 C16 116.8(10) . . . . ? C10 N11 C12 C13 177.8(9) . . . . ? C15 N11 C12 C13 -5.6(11) . . . . ? N11 C12 C13 C14 -16.7(11) . . . . ? C16 C12 C13 C14 -139.3(10) . . . . ? C12 C13 C14 C15 32.3(12) . . . . ? C10 N11 C15 C14 -158.5(10) . . . . ? C12 N11 C15 C14 25.3(12) . . . . ? C13 C14 C15 N11 -35.5(12) . . . . ? N11 C12 C16 O17 -53.3(11) . . . . ? C13 C12 C16 O17 64.4(11) . . . . ? C12 C16 O17 C18 175.0(9) . . . . ? C9 C1 C19 C20 -2.7(15) . . . . ? C10 C1 C19 C20 123.6(11) . . . . ? C2 C1 C19 C20 -113.2(11) . . . . ? C9 C1 C19 C24 178.4(10) . . . . ? C10 C1 C19 C24 -55.3(13) . . . . ? C2 C1 C19 C24 67.9(12) . . . . ? C24 C19 C20 C21 -3.7(16) . . . . ? C1 C19 C20 C21 177.4(11) . . . . ? C19 C20 C21 C22 4.3(18) . . . . ? C20 C21 C22 C23 -1.6(19) . . . . ? C21 C22 C23 C24 -1.3(18) . . . . ? C22 C23 C24 C19 1.8(17) . . . . ? C20 C19 C24 C23 0.7(16) . . . . ? C1 C19 C24 C23 179.7(10) . . . . ? C39 C31 C32 O32 177.0(10) . . . . ? C49 C31 C32 O32 -66.8(13) . . . . ? C40 C31 C32 O32 57.2(14) . . . . ? C39 C31 C32 N33 -6.6(10) . . . . ? C49 C31 C32 N33 109.6(9) . . . . ? C40 C31 C32 N33 -126.4(9) . . . . ? O32 C32 N33 C34 -176.3(10) . . . . ? C31 C32 N33 C34 7.4(11) . . . . ? C32 N33 C34 C39 -5.3(12) . . . . ? C32 N33 C34 C35 176.2(10) . . . . ? N33 C34 C35 C36 -178.4(10) . . . . ? C39 C34 C35 C36 3.2(15) . . . . ? N33 C34 C35 Br35 -4.1(15) . . . . ? C39 C34 C35 Br35 177.5(7) . . . . ? C34 C35 C36 C37 -3.8(15) . . . . ? Br35 C35 C36 C37 -178.1(8) . . . . ? C35 C36 C37 C38 3.9(16) . . . . ? C36 C37 C38 C39 -3.4(15) . . . . ? C37 C38 C39 C34 2.8(15) . . . . ? C37 C38 C39 C31 -179.5(10) . . . . ? N33 C34 C39 C38 178.6(9) . . . . ? C35 C34 C39 C38 -2.8(15) . . . . ? N33 C34 C39 C31 0.5(12) . . . . ? C35 C34 C39 C31 179.1(9) . . . . ? C49 C31 C39 C38 74.3(14) . . . . ? C40 C31 C39 C38 -52.0(14) . . . . ? C32 C31 C39 C38 -174.2(10) . . . . ? C49 C31 C39 C34 -107.8(10) . . . . ? C40 C31 C39 C34 125.9(9) . . . . ? C32 C31 C39 C34 3.7(10) . . . . ? C39 C31 C40 O40 122.0(11) . . . . ? C49 C31 C40 O40 -3.5(14) . . . . ? C32 C31 C40 O40 -123.5(10) . . . . ? C39 C31 C40 N41 -55.7(12) . . . . ? C49 C31 C40 N41 178.7(9) . . . . ? C32 C31 C40 N41 58.7(12) . . . . ? O40 C40 N41 C45 164.5(11) . . . . ? C31 C40 N41 C45 -17.7(15) . . . . ? O40 C40 N41 C42 -12.8(14) . . . . ? C31 C40 N41 C42 165.0(9) . . . . ? C40 N41 C42 C43 -179.6(9) . . . . ? C45 N41 C42 C43 2.6(11) . . . . ? C40 N41 C42 C46 -60.0(12) . . . . ? C45 N41 C42 C46 122.3(10) . . . . ? N41 C42 C43 C44 -24.6(11) . . . . ? C46 C42 C43 C44 -141.9(9) . . . . ? C42 C43 C44 C45 38.1(11) . . . . ? C40 N41 C45 C44 -156.4(10) . . . . ? C42 N41 C45 C44 21.1(12) . . . . ? C43 C44 C45 N41 -35.6(11) . . . . ? N41 C42 C46 O47 -171.1(8) . . . . ? C43 C42 C46 O47 -56.7(12) . . . . ? C42 C46 O47 C48 -177.7(10) . . . . ? C39 C31 C49 C50 -1.7(15) . . . . ? C40 C31 C49 C50 123.6(12) . . . . ? C32 C31 C49 C50 -111.1(11) . . . . ? C39 C31 C49 C54 177.0(9) . . . . ? C40 C31 C49 C54 -57.6(13) . . . . ? C32 C31 C49 C54 67.7(12) . . . . ? C54 C49 C50 C51 -2.7(17) . . . . ? C31 C49 C50 C51 176.1(10) . . . . ? C49 C50 C51 C52 1.8(19) . . . . ? C50 C51 C52 C53 0(2) . . . . ? C51 C52 C53 C54 -1.1(19) . . . . ? C52 C53 C54 C49 0.2(18) . . . . ? C50 C49 C54 C53 1.7(17) . . . . ? C31 C49 C54 C53 -177.2(10) . . . . ? 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 N3 H3N O10 0.9800(11) 2.12(8) 2.845(11) 129(7) 2_645 N33 H33N O40 0.9800(11) 1.79(4) 2.706(11) 153(8) 2_646 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 67.98 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.494 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.113 # Attachment '8f.CIF' data_8f _database_code_depnum_ccdc_archive 'CCDC 609782' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H21 Cl N2 O3' _chemical_formula_sum 'C21 H21 Cl N2 O3' _chemical_formula_weight 384.85 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.9714(7) _cell_length_b 14.1418(11) _cell_length_c 15.1487(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1921.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 10817 _cell_measurement_theta_min 1.12 _cell_measurement_theta_max 28.22 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.080 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.223 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9016 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13683 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0116 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3381 _reflns_number_gt 3349 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0314P)^2^+0.4603P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(4) _refine_ls_number_reflns 3381 _refine_ls_number_parameters 249 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0224 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_ref 0.0555 _refine_ls_wR_factor_gt 0.0554 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 -0.55382(13) -0.57233(8) -0.79849(8) 0.0141(3) Uani 1 1 d . . . C2 C -0.49598(14) -0.46799(8) -0.79236(8) 0.0142(2) Uani 1 1 d . . . O2 O -0.36625(10) -0.44284(6) -0.78916(7) 0.0194(2) Uani 1 1 d . . . N3 N -0.61785(11) -0.40952(7) -0.79392(7) 0.0144(2) Uani 1 1 d D . . H3N H -0.6117(19) -0.34060(16) -0.7884(11) 0.031(4) Uiso 1 1 d D . . C4 C -0.75024(13) -0.46084(8) -0.78932(8) 0.0134(2) Uani 1 1 d . . . C5 C -0.89575(14) -0.42851(8) -0.78548(8) 0.0143(2) Uani 1 1 d . . . Cl5 Cl -0.92938(3) -0.30754(2) -0.79250(2) 0.01851(8) Uani 1 1 d . . . C6 C -1.01290(14) -0.49225(9) -0.77848(8) 0.0163(3) Uani 1 1 d . . . H6A H -1.1128 -0.4702 -0.7758 0.020 Uiso 1 1 calc R . . C7 C -0.98277(15) -0.58885(9) -0.77536(8) 0.0179(3) Uani 1 1 d . . . H7A H -1.0629 -0.6324 -0.7702 0.021 Uiso 1 1 calc R . . C8 C -0.83575(14) -0.62276(9) -0.77970(9) 0.0161(3) Uani 1 1 d . . . H8A H -0.8159 -0.6887 -0.7774 0.019 Uiso 1 1 calc R . . C9 C -0.72055(13) -0.55849(8) -0.78740(8) 0.0139(2) Uani 1 1 d . . . C10 C -0.48561(14) -0.63789(8) -0.72684(8) 0.0144(3) Uani 1 1 d . . . O10 O -0.43089(10) -0.71457(6) -0.74834(6) 0.01808(19) Uani 1 1 d . . . N11 N -0.49065(12) -0.60933(7) -0.64226(7) 0.0159(2) Uani 1 1 d . . . C12 C -0.41283(15) -0.66556(9) -0.57340(8) 0.0167(3) Uani 1 1 d . . . H12A H -0.3133 -0.6864 -0.5959 0.020 Uiso 1 1 calc R . . C13 C -0.39190(15) -0.59379(10) -0.49868(9) 0.0198(3) Uani 1 1 d . . . H13A H -0.3000 -0.5562 -0.5072 0.024 Uiso 1 1 calc R . . H13B H -0.3875 -0.6256 -0.4405 0.024 Uiso 1 1 calc R . . C14 C -0.53143(16) -0.53166(10) -0.50654(9) 0.0209(3) Uani 1 1 d . . . H14A H -0.6202 -0.5640 -0.4822 0.025 Uiso 1 1 calc R . . H14B H -0.5178 -0.4705 -0.4758 0.025 Uiso 1 1 calc R . . C15 C -0.54511(16) -0.51781(9) -0.60649(9) 0.0199(3) Uani 1 1 d . . . H15A H -0.6498 -0.5060 -0.6239 0.024 Uiso 1 1 calc R . . H15B H -0.4824 -0.4646 -0.6270 0.024 Uiso 1 1 calc R . . C16 C -0.50356(15) -0.75149(9) -0.54492(9) 0.0182(3) Uani 1 1 d . . . H16A H -0.5879 -0.7321 -0.5069 0.022 Uiso 1 1 calc R . . H16B H -0.5434 -0.7854 -0.5970 0.022 Uiso 1 1 calc R . . O17 O -0.40261(11) -0.80998(7) -0.49732(6) 0.0224(2) Uani 1 1 d . . . C18 C -0.47340(17) -0.89102(10) -0.46131(10) 0.0232(3) Uani 1 1 d . . . H18A H -0.3999 -0.9291 -0.4293 0.035 Uiso 1 1 calc R . . H18B H -0.5167 -0.9288 -0.5091 0.035 Uiso 1 1 calc R . . H18C H -0.5524 -0.8711 -0.4207 0.035 Uiso 1 1 calc R . . C19 C -0.51099(15) -0.60755(8) -0.89178(8) 0.0152(3) Uani 1 1 d . . . C20 C -0.61799(16) -0.62941(9) -0.95526(9) 0.0202(3) Uani 1 1 d . . . H20A H -0.7208 -0.6264 -0.9405 0.024 Uiso 1 1 calc R . . C21 C -0.57512(18) -0.65573(10) -1.04054(10) 0.0259(3) Uani 1 1 d . . . H21A H -0.6488 -0.6703 -1.0835 0.031 Uiso 1 1 calc R . . C22 C -0.42531(18) -0.66059(10) -1.06248(9) 0.0260(3) Uani 1 1 d . . . H22A H -0.3961 -0.6779 -1.1206 0.031 Uiso 1 1 calc R . . C23 C -0.31764(16) -0.64001(10) -0.99894(10) 0.0239(3) Uani 1 1 d . . . H23A H -0.2149 -0.6440 -1.0136 0.029 Uiso 1 1 calc R . . C24 C -0.36010(16) -0.61376(10) -0.91427(10) 0.0203(3) Uani 1 1 d . . . H24A H -0.2861 -0.5999 -0.8713 0.024 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 C1 0.0130(6) 0.0134(6) 0.0161(6) -0.0007(5) 0.0001(5) 0.0005(5) C2 0.0148(6) 0.0153(6) 0.0125(6) 0.0002(5) 0.0010(5) 0.0016(5) O2 0.0135(4) 0.0186(4) 0.0261(5) -0.0006(4) -0.0001(4) -0.0010(3) N3 0.0140(5) 0.0114(5) 0.0177(5) 0.0003(5) -0.0001(4) -0.0004(4) C4 0.0158(6) 0.0136(6) 0.0109(6) 0.0008(5) -0.0018(5) -0.0013(5) C5 0.0176(6) 0.0125(6) 0.0127(6) 0.0008(5) -0.0003(5) 0.0027(5) Cl5 0.01773(14) 0.01251(14) 0.02527(16) 0.00025(12) 0.00074(13) 0.00394(12) C6 0.0145(6) 0.0197(6) 0.0148(6) 0.0012(5) -0.0005(5) 0.0007(5) C7 0.0162(6) 0.0193(6) 0.0181(7) 0.0027(5) -0.0011(5) -0.0045(5) C8 0.0184(6) 0.0127(6) 0.0171(6) 0.0013(5) -0.0014(5) -0.0017(5) C9 0.0144(6) 0.0144(6) 0.0128(6) -0.0002(5) -0.0010(5) 0.0022(5) C10 0.0117(5) 0.0133(6) 0.0183(7) 0.0007(5) 0.0012(5) -0.0004(5) O10 0.0214(4) 0.0140(4) 0.0189(4) 0.0010(4) 0.0000(4) 0.0047(4) N11 0.0173(5) 0.0137(5) 0.0168(5) -0.0002(4) 0.0000(4) 0.0034(4) C12 0.0158(6) 0.0182(6) 0.0161(6) 0.0010(5) -0.0017(5) 0.0028(5) C13 0.0205(7) 0.0215(6) 0.0175(6) -0.0016(6) -0.0040(5) 0.0001(5) C14 0.0244(7) 0.0209(7) 0.0176(7) -0.0027(5) -0.0007(5) 0.0033(5) C15 0.0244(7) 0.0161(6) 0.0192(7) -0.0029(5) 0.0003(5) 0.0054(5) C16 0.0174(6) 0.0196(7) 0.0176(6) 0.0008(5) -0.0013(5) 0.0029(5) O17 0.0205(5) 0.0202(5) 0.0265(5) 0.0075(4) -0.0045(4) 0.0014(4) C18 0.0281(8) 0.0191(7) 0.0224(7) 0.0034(5) 0.0016(6) 0.0013(6) C19 0.0209(6) 0.0087(6) 0.0160(6) 0.0008(5) 0.0016(5) 0.0021(5) C20 0.0217(7) 0.0176(7) 0.0212(7) 0.0007(5) -0.0008(6) 0.0011(5) C21 0.0324(8) 0.0249(7) 0.0205(7) -0.0035(6) -0.0030(6) -0.0015(7) C22 0.0369(8) 0.0226(7) 0.0184(7) -0.0035(5) 0.0054(6) 0.0031(7) C23 0.0249(7) 0.0208(7) 0.0259(8) -0.0001(6) 0.0077(6) 0.0045(6) C24 0.0207(7) 0.0174(7) 0.0227(7) 0.0007(5) -0.0004(5) 0.0028(5) _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 C9 1.5179(17) . ? C1 C19 1.5469(17) . ? C1 C10 1.5531(17) . ? C1 C2 1.5669(16) . ? C2 O2 1.2179(15) . ? C2 N3 1.3710(16) . ? N3 C4 1.3936(16) . ? N3 H3N 0.9797(10) . ? C4 C5 1.3844(17) . ? C4 C9 1.4068(17) . ? C5 C6 1.3886(18) . ? C5 Cl5 1.7404(12) . ? C6 C7 1.3934(19) . ? C6 H6A 0.9500 . ? C7 C8 1.4050(18) . ? C7 H7A 0.9500 . ? C8 C9 1.3812(18) . ? C8 H8A 0.9500 . ? C10 O10 1.2341(15) . ? C10 N11 1.3441(17) . ? N11 C15 1.4858(16) . ? N11 C12 1.4859(16) . ? C12 C16 1.5249(18) . ? C12 C13 1.5319(18) . ? C12 H12A 1.0000 . ? C13 C14 1.5340(19) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.5316(19) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O17 1.4228(16) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? O17 C18 1.4192(17) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.394(2) . ? C19 C24 1.3987(19) . ? C20 C21 1.398(2) . ? C20 H20A 0.9500 . ? C21 C22 1.386(2) . ? C21 H21A 0.9500 . ? C22 C23 1.394(2) . ? C22 H22A 0.9500 . ? C23 C24 1.389(2) . ? C23 H23A 0.9500 . ? C24 H24A 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 C9 C1 C19 112.79(10) . . ? C9 C1 C10 112.82(10) . . ? C19 C1 C10 110.39(10) . . ? C9 C1 C2 101.44(9) . . ? C19 C1 C2 105.97(10) . . ? C10 C1 C2 112.97(10) . . ? O2 C2 N3 125.93(11) . . ? O2 C2 C1 126.42(11) . . ? N3 C2 C1 107.63(10) . . ? C2 N3 C4 111.39(10) . . ? C2 N3 H3N 123.6(10) . . ? C4 N3 H3N 124.2(10) . . ? C5 C4 N3 129.33(11) . . ? C5 C4 C9 120.12(11) . . ? N3 C4 C9 110.54(10) . . ? C4 C5 C6 120.17(11) . . ? C4 C5 Cl5 119.04(9) . . ? C6 C5 Cl5 120.76(9) . . ? C5 C6 C7 119.48(12) . . ? C5 C6 H6A 120.3 . . ? C7 C6 H6A 120.3 . . ? C6 C7 C8 121.01(12) . . ? C6 C7 H7A 119.5 . . ? C8 C7 H7A 119.5 . . ? C9 C8 C7 118.80(11) . . ? C9 C8 H8A 120.6 . . ? C7 C8 H8A 120.6 . . ? C8 C9 C4 120.40(11) . . ? C8 C9 C1 131.45(11) . . ? C4 C9 C1 108.11(10) . . ? O10 C10 N11 121.94(11) . . ? O10 C10 C1 119.79(11) . . ? N11 C10 C1 118.26(11) . . ? C10 N11 C15 128.35(11) . . ? C10 N11 C12 119.51(10) . . ? C15 N11 C12 111.39(10) . . ? N11 C12 C16 111.98(10) . . ? N11 C12 C13 102.81(10) . . ? C16 C12 C13 112.60(11) . . ? N11 C12 H12A 109.8 . . ? C16 C12 H12A 109.8 . . ? C13 C12 H12A 109.8 . . ? C12 C13 C14 102.84(11) . . ? C12 C13 H13A 111.2 . . ? C14 C13 H13A 111.2 . . ? C12 C13 H13B 111.2 . . ? C14 C13 H13B 111.2 . . ? H13A C13 H13B 109.1 . . ? C15 C14 C13 102.44(11) . . ? C15 C14 H14A 111.3 . . ? C13 C14 H14A 111.3 . . ? C15 C14 H14B 111.3 . . ? C13 C14 H14B 111.3 . . ? H14A C14 H14B 109.2 . . ? N11 C15 C14 102.87(10) . . ? N11 C15 H15A 111.2 . . ? C14 C15 H15A 111.2 . . ? N11 C15 H15B 111.2 . . ? C14 C15 H15B 111.2 . . ? H15A C15 H15B 109.1 . . ? O17 C16 C12 105.48(10) . . ? O17 C16 H16A 110.6 . . ? C12 C16 H16A 110.6 . . ? O17 C16 H16B 110.6 . . ? C12 C16 H16B 110.6 . . ? H16A C16 H16B 108.8 . . ? C18 O17 C16 112.30(10) . . ? O17 C18 H18A 109.5 . . ? O17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 118.99(12) . . ? C20 C19 C1 122.07(12) . . ? C24 C19 C1 118.89(12) . . ? C19 C20 C21 120.48(14) . . ? C19 C20 H20A 119.8 . . ? C21 C20 H20A 119.8 . . ? C22 C21 C20 120.09(14) . . ? C22 C21 H21A 120.0 . . ? C20 C21 H21A 120.0 . . ? C21 C22 C23 119.73(13) . . ? C21 C22 H22A 120.1 . . ? C23 C22 H22A 120.1 . . ? C24 C23 C22 120.23(13) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 119.9 . . ? C23 C24 C19 120.48(13) . . ? C23 C24 H24A 119.8 . . ? C19 C24 H24A 119.8 . . ? 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 C1 C2 O2 172.48(14) . . . . ? C19 C1 C2 O2 -69.55(17) . . . . ? C10 C1 C2 O2 51.44(18) . . . . ? C9 C1 C2 N3 -9.31(13) . . . . ? C19 C1 C2 N3 108.66(11) . . . . ? C10 C1 C2 N3 -130.35(11) . . . . ? O2 C2 N3 C4 -174.43(13) . . . . ? C1 C2 N3 C4 7.35(14) . . . . ? C2 N3 C4 C5 177.05(13) . . . . ? C2 N3 C4 C9 -2.00(15) . . . . ? N3 C4 C5 C6 -178.07(12) . . . . ? C9 C4 C5 C6 0.90(19) . . . . ? N3 C4 C5 Cl5 3.61(19) . . . . ? C9 C4 C5 Cl5 -177.42(10) . . . . ? C4 C5 C6 C7 0.00(18) . . . . ? Cl5 C5 C6 C7 178.29(10) . . . . ? C5 C6 C7 C8 -0.38(19) . . . . ? C6 C7 C8 C9 -0.16(19) . . . . ? C7 C8 C9 C4 1.06(19) . . . . ? C7 C8 C9 C1 -176.19(13) . . . . ? C5 C4 C9 C8 -1.44(19) . . . . ? N3 C4 C9 C8 177.70(12) . . . . ? C5 C4 C9 C1 176.39(12) . . . . ? N3 C4 C9 C1 -4.46(15) . . . . ? C19 C1 C9 C8 72.71(17) . . . . ? C10 C1 C9 C8 -53.22(18) . . . . ? C2 C1 C9 C8 -174.36(13) . . . . ? C19 C1 C9 C4 -104.80(12) . . . . ? C10 C1 C9 C4 129.27(11) . . . . ? C2 C1 C9 C4 8.13(13) . . . . ? C9 C1 C10 O10 115.29(13) . . . . ? C19 C1 C10 O10 -11.92(16) . . . . ? C2 C1 C10 O10 -130.37(12) . . . . ? C9 C1 C10 N11 -63.59(15) . . . . ? C19 C1 C10 N11 169.20(11) . . . . ? C2 C1 C10 N11 50.75(15) . . . . ? O10 C10 N11 C15 176.52(12) . . . . ? C1 C10 N11 C15 -4.62(19) . . . . ? O10 C10 N11 C12 7.39(18) . . . . ? C1 C10 N11 C12 -173.75(11) . . . . ? C10 N11 C12 C16 -80.30(15) . . . . ? C15 N11 C12 C16 108.85(12) . . . . ? C10 N11 C12 C13 158.59(11) . . . . ? C15 N11 C12 C13 -12.27(14) . . . . ? N11 C12 C13 C14 33.40(13) . . . . ? C16 C12 C13 C14 -87.29(13) . . . . ? C12 C13 C14 C15 -42.37(13) . . . . ? C10 N11 C15 C14 176.29(13) . . . . ? C12 N11 C15 C14 -13.86(14) . . . . ? C13 C14 C15 N11 34.24(13) . . . . ? N11 C12 C16 O17 165.73(10) . . . . ? C13 C12 C16 O17 -79.00(13) . . . . ? C12 C16 O17 C18 176.31(11) . . . . ? C9 C1 C19 C20 -3.91(16) . . . . ? C10 C1 C19 C20 123.31(12) . . . . ? C2 C1 C19 C20 -114.04(13) . . . . ? C9 C1 C19 C24 173.31(11) . . . . ? C10 C1 C19 C24 -59.47(15) . . . . ? C2 C1 C19 C24 63.18(14) . . . . ? C24 C19 C20 C21 -0.99(19) . . . . ? C1 C19 C20 C21 176.23(12) . . . . ? C19 C20 C21 C22 0.2(2) . . . . ? C20 C21 C22 C23 0.6(2) . . . . ? C21 C22 C23 C24 -0.7(2) . . . . ? C22 C23 C24 C19 -0.1(2) . . . . ? C20 C19 C24 C23 0.9(2) . . . . ? C1 C19 C24 C23 -176.39(11) . . . . ? 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 N3 H3N O10 0.9797(10) 1.906(5) 2.8639(13) 165.1(15) 3_453 _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.163 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.029 # Attachment '8g.CIF' data_8g _database_code_depnum_ccdc_archive 'CCDC 609783' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H21 F N2 O3' _chemical_formula_sum 'C21 H21 F N2 O3' _chemical_formula_weight 368.40 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.797(2) _cell_length_b 12.303(2) _cell_length_c 14.883(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1793.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 6578 _cell_measurement_theta_min 1.6542 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.0500 _exptl_crystal_size_mid 0.0500 _exptl_crystal_size_min 0.0500 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8034 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11683 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3208 _reflns_number_gt 2956 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0416P)^2^+0.1648P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(8) _refine_ls_number_reflns 3208 _refine_ls_number_parameters 249 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0837 _refine_ls_wR_factor_gt 0.0812 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.084 _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 C1 C 0.53748(17) 0.16725(13) 0.23259(11) 0.0154(4) Uani 1 1 d . . . C2 C 0.49770(18) 0.29013(14) 0.23964(11) 0.0171(4) Uani 1 1 d . . . O2 O 0.38627(12) 0.32891(10) 0.22523(9) 0.0226(3) Uani 1 1 d . . . N3 N 0.61021(15) 0.34460(11) 0.27093(10) 0.0193(3) Uani 1 1 d D . . H3N H 0.614(2) 0.4214(5) 0.2881(14) 0.041(6) Uiso 1 1 d D . . C4 C 0.72534(18) 0.27746(14) 0.27136(12) 0.0173(4) Uani 1 1 d . . . C5 C 0.85945(18) 0.30374(14) 0.28673(13) 0.0202(4) Uani 1 1 d . . . F5 F 0.89232(11) 0.40672(8) 0.31141(7) 0.0298(3) Uani 1 1 d . . . C6 C 0.96055(19) 0.22680(15) 0.27600(12) 0.0218(4) Uani 1 1 d . . . H6A H 1.0533 0.2452 0.2867 0.026 Uiso 1 1 calc R . . C7 C 0.92577(19) 0.12207(15) 0.24935(12) 0.0210(4) Uani 1 1 d . . . H7A H 0.9956 0.0694 0.2410 0.025 Uiso 1 1 calc R . . C8 C 0.79029(19) 0.09324(15) 0.23478(12) 0.0194(4) Uani 1 1 d . . . H8A H 0.7668 0.0214 0.2174 0.023 Uiso 1 1 calc R . . C9 C 0.69046(17) 0.17180(14) 0.24626(11) 0.0159(4) Uani 1 1 d . . . C10 C 0.49814(17) 0.11470(14) 0.14158(11) 0.0160(4) Uani 1 1 d . . . O10 O 0.40990(12) 0.04328(9) 0.13850(8) 0.0189(3) Uani 1 1 d . . . N11 N 0.56520(15) 0.14518(11) 0.06777(10) 0.0185(4) Uani 1 1 d . . . C12 C 0.54907(19) 0.08309(14) -0.01718(12) 0.0205(4) Uani 1 1 d . . . H12A H 0.4526 0.0899 -0.0383 0.025 Uiso 1 1 calc R . . C13 C 0.6424(2) 0.14311(15) -0.08262(13) 0.0246(4) Uani 1 1 d . . . H13A H 0.7342 0.1096 -0.0840 0.029 Uiso 1 1 calc R . . H13B H 0.6038 0.1423 -0.1441 0.029 Uiso 1 1 calc R . . C14 C 0.6492(2) 0.25838(15) -0.04618(13) 0.0270(5) Uani 1 1 d . . . H14A H 0.5662 0.3002 -0.0619 0.032 Uiso 1 1 calc R . . H14B H 0.7306 0.2973 -0.0689 0.032 Uiso 1 1 calc R . . C15 C 0.6586(2) 0.23869(15) 0.05503(14) 0.0250(4) Uani 1 1 d . . . H15A H 0.7529 0.2203 0.0733 0.030 Uiso 1 1 calc R . . H15B H 0.6274 0.3030 0.0894 0.030 Uiso 1 1 calc R . . C16 C 0.5836(2) -0.03651(14) -0.00654(13) 0.0232(4) Uani 1 1 d . . . H16A H 0.5146 -0.0724 0.0320 0.028 Uiso 1 1 calc R . . H16B H 0.5830 -0.0726 -0.0660 0.028 Uiso 1 1 calc R . . O17 O 0.71465(14) -0.04615(10) 0.03316(9) 0.0282(3) Uani 1 1 d . . . C18 C 0.7458(2) -0.15674(17) 0.05163(16) 0.0378(5) Uani 1 1 d . . . H18A H 0.8367 -0.1616 0.0787 0.057 Uiso 1 1 calc R . . H18B H 0.7442 -0.1985 -0.0045 0.057 Uiso 1 1 calc R . . H18C H 0.6779 -0.1864 0.0933 0.057 Uiso 1 1 calc R . . C19 C 0.46180(18) 0.11316(14) 0.31148(12) 0.0164(4) Uani 1 1 d . . . C20 C 0.53082(19) 0.07127(14) 0.38495(11) 0.0205(4) Uani 1 1 d . . . H20A H 0.6278 0.0701 0.3850 0.025 Uiso 1 1 calc R . . C21 C 0.4598(2) 0.03082(15) 0.45870(13) 0.0254(4) Uani 1 1 d . . . H21A H 0.5087 0.0029 0.5088 0.031 Uiso 1 1 calc R . . C22 C 0.3191(2) 0.03102(15) 0.45961(13) 0.0241(4) Uani 1 1 d . . . H22A H 0.2704 0.0042 0.5102 0.029 Uiso 1 1 calc R . . C23 C 0.2499(2) 0.07107(15) 0.38548(12) 0.0229(4) Uani 1 1 d . . . H23A H 0.1529 0.0705 0.3851 0.027 Uiso 1 1 calc R . . C24 C 0.31939(18) 0.11183(14) 0.31213(13) 0.0193(4) Uani 1 1 d . . . H24A H 0.2701 0.1390 0.2620 0.023 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 C1 0.0175(9) 0.0136(8) 0.0150(8) -0.0013(8) 0.0002(7) 0.0008(7) C2 0.0186(9) 0.0174(9) 0.0154(9) 0.0008(7) 0.0013(7) 0.0011(7) O2 0.0191(7) 0.0211(6) 0.0277(7) 0.0031(6) -0.0016(6) 0.0044(5) N3 0.0202(8) 0.0141(7) 0.0235(8) -0.0019(7) 0.0001(7) -0.0003(6) C4 0.0196(9) 0.0170(8) 0.0154(9) 0.0024(8) 0.0017(7) 0.0012(7) C5 0.0208(10) 0.0188(9) 0.0210(10) -0.0009(8) -0.0027(8) -0.0066(8) F5 0.0275(6) 0.0204(5) 0.0415(7) -0.0023(5) -0.0054(6) -0.0074(5) C6 0.0173(9) 0.0273(10) 0.0209(9) 0.0042(9) -0.0017(8) -0.0016(8) C7 0.0188(10) 0.0243(10) 0.0200(9) 0.0016(8) 0.0009(8) 0.0050(8) C8 0.0218(9) 0.0187(9) 0.0179(9) 0.0016(8) -0.0004(8) 0.0006(8) C9 0.0169(9) 0.0170(9) 0.0138(9) 0.0017(7) 0.0002(7) -0.0009(7) C10 0.0147(9) 0.0148(9) 0.0183(9) 0.0022(8) -0.0008(8) 0.0034(8) O10 0.0198(6) 0.0175(6) 0.0196(6) 0.0005(5) -0.0008(6) -0.0036(5) N11 0.0217(8) 0.0186(8) 0.0153(8) -0.0018(6) 0.0008(6) -0.0041(6) C12 0.0207(9) 0.0239(9) 0.0168(9) -0.0043(8) -0.0010(8) -0.0005(8) C13 0.0284(11) 0.0271(10) 0.0182(10) 0.0023(8) 0.0036(8) 0.0012(8) C14 0.0345(12) 0.0249(10) 0.0217(10) 0.0051(8) 0.0045(9) -0.0056(9) C15 0.0275(11) 0.0253(10) 0.0222(10) 0.0035(9) 0.0032(8) -0.0086(8) C16 0.0261(11) 0.0214(9) 0.0220(10) -0.0042(8) -0.0001(8) -0.0023(8) O17 0.0300(8) 0.0245(7) 0.0300(8) 0.0043(6) -0.0047(6) 0.0036(6) C18 0.0429(13) 0.0311(12) 0.0394(13) 0.0116(10) 0.0066(11) 0.0094(10) C19 0.0193(9) 0.0125(8) 0.0173(9) -0.0021(8) 0.0022(7) -0.0009(7) C20 0.0193(10) 0.0219(10) 0.0203(10) 0.0021(8) -0.0006(8) -0.0019(7) C21 0.0309(11) 0.0260(10) 0.0194(10) 0.0040(9) -0.0039(8) -0.0021(8) C22 0.0264(11) 0.0242(10) 0.0216(10) 0.0036(9) 0.0055(8) -0.0034(8) C23 0.0191(10) 0.0214(10) 0.0281(11) -0.0005(9) 0.0024(8) -0.0017(7) C24 0.0209(10) 0.0158(9) 0.0211(9) -0.0001(8) -0.0008(8) 0.0025(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 C1 C9 1.514(2) . ? C1 C19 1.540(2) . ? C1 C10 1.550(2) . ? C1 C2 1.565(2) . ? C2 O2 1.211(2) . ? C2 N3 1.371(2) . ? N3 C4 1.398(2) . ? C4 C5 1.372(2) . ? C4 C9 1.395(2) . ? C5 F5 1.358(2) . ? C5 C6 1.379(3) . ? C6 C7 1.390(3) . ? C7 C8 1.391(3) . ? C8 C9 1.386(2) . ? C10 O10 1.233(2) . ? C10 N11 1.334(2) . ? N11 C15 1.482(2) . ? N11 C12 1.486(2) . ? C12 C16 1.518(3) . ? C12 C13 1.526(3) . ? C13 C14 1.520(3) . ? C14 C15 1.528(3) . ? C16 O17 1.419(2) . ? O17 C18 1.421(2) . ? C19 C20 1.385(2) . ? C19 C24 1.395(2) . ? C20 C21 1.392(3) . ? C21 C22 1.379(3) . ? C22 C23 1.386(3) . ? C23 C24 1.381(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 C1 C19 112.98(14) . . ? C9 C1 C10 112.29(14) . . ? C19 C1 C10 111.49(13) . . ? C9 C1 C2 101.64(14) . . ? C19 C1 C2 104.27(13) . . ? C10 C1 C2 113.57(13) . . ? O2 C2 N3 126.33(15) . . ? O2 C2 C1 126.40(16) . . ? N3 C2 C1 107.14(14) . . ? C2 N3 C4 111.18(13) . . ? C5 C4 C9 119.92(16) . . ? C5 C4 N3 129.35(16) . . ? C9 C4 N3 110.59(15) . . ? F5 C5 C4 119.47(16) . . ? F5 C5 C6 120.09(15) . . ? C4 C5 C6 120.44(16) . . ? C5 C6 C7 119.53(17) . . ? C6 C7 C8 120.97(17) . . ? C9 C8 C7 118.46(17) . . ? C8 C9 C4 120.67(16) . . ? C8 C9 C1 131.04(16) . . ? C4 C9 C1 108.24(15) . . ? O10 C10 N11 120.99(15) . . ? O10 C10 C1 120.27(15) . . ? N11 C10 C1 118.69(14) . . ? C10 N11 C15 128.88(15) . . ? C10 N11 C12 120.26(14) . . ? C15 N11 C12 110.85(14) . . ? N11 C12 C16 112.70(14) . . ? N11 C12 C13 103.34(14) . . ? C16 C12 C13 113.72(16) . . ? C14 C13 C12 104.48(15) . . ? C13 C14 C15 101.92(14) . . ? N11 C15 C14 102.24(15) . . ? O17 C16 C12 109.03(14) . . ? C16 O17 C18 110.78(15) . . ? C20 C19 C24 118.58(17) . . ? C20 C19 C1 121.84(16) . . ? C24 C19 C1 119.46(16) . . ? C19 C20 C21 120.78(18) . . ? C22 C21 C20 120.46(19) . . ? C21 C22 C23 118.83(18) . . ? C24 C23 C22 121.14(17) . . ? C23 C24 C19 120.19(17) . . ? 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 C1 C2 O2 173.03(17) . . . . ? C19 C1 C2 O2 -69.3(2) . . . . ? C10 C1 C2 O2 52.2(2) . . . . ? C9 C1 C2 N3 -10.89(18) . . . . ? C19 C1 C2 N3 106.74(16) . . . . ? C10 C1 C2 N3 -131.71(15) . . . . ? O2 C2 N3 C4 -174.07(17) . . . . ? C1 C2 N3 C4 9.84(19) . . . . ? C2 N3 C4 C5 170.99(19) . . . . ? C2 N3 C4 C9 -4.5(2) . . . . ? C9 C4 C5 F5 -179.79(15) . . . . ? N3 C4 C5 F5 5.1(3) . . . . ? C9 C4 C5 C6 1.1(3) . . . . ? N3 C4 C5 C6 -174.00(17) . . . . ? F5 C5 C6 C7 -179.01(16) . . . . ? C4 C5 C6 C7 0.0(3) . . . . ? C5 C6 C7 C8 -1.1(3) . . . . ? C6 C7 C8 C9 0.9(3) . . . . ? C7 C8 C9 C4 0.4(3) . . . . ? C7 C8 C9 C1 177.52(18) . . . . ? C5 C4 C9 C8 -1.4(3) . . . . ? N3 C4 C9 C8 174.63(16) . . . . ? C5 C4 C9 C1 -179.11(16) . . . . ? N3 C4 C9 C1 -3.11(19) . . . . ? C19 C1 C9 C8 79.7(2) . . . . ? C10 C1 C9 C8 -47.4(2) . . . . ? C2 C1 C9 C8 -169.13(18) . . . . ? C19 C1 C9 C4 -102.84(16) . . . . ? C10 C1 C9 C4 130.01(15) . . . . ? C2 C1 C9 C4 8.30(18) . . . . ? C9 C1 C10 O10 131.95(17) . . . . ? C19 C1 C10 O10 4.0(2) . . . . ? C2 C1 C10 O10 -113.42(17) . . . . ? C9 C1 C10 N11 -45.4(2) . . . . ? C19 C1 C10 N11 -173.38(14) . . . . ? C2 C1 C10 N11 69.2(2) . . . . ? O10 C10 N11 C15 170.21(17) . . . . ? C1 C10 N11 C15 -12.4(3) . . . . ? O10 C10 N11 C12 -8.7(2) . . . . ? C1 C10 N11 C12 168.69(14) . . . . ? C10 N11 C12 C16 -56.2(2) . . . . ? C15 N11 C12 C16 124.72(16) . . . . ? C10 N11 C12 C13 -179.37(15) . . . . ? C15 N11 C12 C13 1.54(19) . . . . ? N11 C12 C13 C14 -26.13(18) . . . . ? C16 C12 C13 C14 -148.63(16) . . . . ? C12 C13 C14 C15 40.43(19) . . . . ? C10 N11 C15 C14 -155.73(17) . . . . ? C12 N11 C15 C14 23.25(19) . . . . ? C13 C14 C15 N11 -38.38(18) . . . . ? N11 C12 C16 O17 -52.3(2) . . . . ? C13 C12 C16 O17 64.91(19) . . . . ? C12 C16 O17 C18 174.83(16) . . . . ? C9 C1 C19 C20 -1.7(2) . . . . ? C10 C1 C19 C20 125.85(17) . . . . ? C2 C1 C19 C20 -111.23(17) . . . . ? C9 C1 C19 C24 174.30(16) . . . . ? C10 C1 C19 C24 -58.1(2) . . . . ? C2 C1 C19 C24 64.79(19) . . . . ? C24 C19 C20 C21 -1.4(3) . . . . ? C1 C19 C20 C21 174.70(16) . . . . ? C19 C20 C21 C22 0.5(3) . . . . ? C20 C21 C22 C23 0.7(3) . . . . ? C21 C22 C23 C24 -1.0(3) . . . . ? C22 C23 C24 C19 0.1(3) . . . . ? C20 C19 C24 C23 1.1(3) . . . . ? C1 C19 C24 C23 -175.09(16) . . . . ? 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 N3 H3N O10 0.9799(11) 1.869(9) 2.7984(19) 157.1(19) 3_655 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.143 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.042 # Attachment '8i.cif' data_8i _database_code_depnum_ccdc_archive 'CCDC 609784' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 Br N2 O3' _chemical_formula_sum 'C16 H19 Br N2 O3' _chemical_formula_weight 367.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.5669(14) _cell_length_b 12.7503(16) _cell_length_c 14.900(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1627.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 6532 _cell_measurement_theta_min 2.1038 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.0300 _exptl_crystal_size_min 0.0300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 2.539 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7533 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10463 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.33 _reflns_number_total 2932 _reflns_number_gt 2707 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0323P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.005(7) _refine_ls_number_reflns 2932 _refine_ls_number_parameters 204 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0230 _refine_ls_R_factor_gt 0.0206 _refine_ls_wR_factor_ref 0.0479 _refine_ls_wR_factor_gt 0.0468 _refine_ls_goodness_of_fit_ref 0.776 _refine_ls_restrained_S_all 0.776 _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 0.5121(3) 0.79215(16) 0.25073(14) 0.0141(4) Uani 1 1 d . . . C2 C 0.4775(3) 0.67248(15) 0.25595(14) 0.0156(5) Uani 1 1 d . . . O2 O 0.40126(19) 0.62842(11) 0.31380(10) 0.0218(4) Uani 1 1 d . . . N3 N 0.5402(2) 0.62687(12) 0.18111(11) 0.0146(4) Uani 1 1 d D . . H3N H 0.527(3) 0.5531(6) 0.1645(18) 0.048(8) Uiso 1 1 d D . . C4 C 0.6273(2) 0.69838(14) 0.13066(14) 0.0120(4) Uani 1 1 d . . . C5 C 0.7161(3) 0.68303(14) 0.05497(14) 0.0157(4) Uani 1 1 d . . . Br5 Br 0.72510(2) 0.548155(13) 0.000487(16) 0.02027(7) Uani 1 1 d . . . C6 C 0.7997(3) 0.76678(15) 0.01903(14) 0.0185(5) Uani 1 1 d . . . H6A H 0.8632 0.7563 -0.0325 0.022 Uiso 1 1 calc R . . C7 C 0.7910(3) 0.86443(15) 0.05775(14) 0.0205(5) Uani 1 1 d . . . H7A H 0.8484 0.9209 0.0325 0.025 Uiso 1 1 calc R . . C8 C 0.6985(3) 0.88193(15) 0.13401(14) 0.0169(5) Uani 1 1 d . . . H8A H 0.6916 0.9497 0.1602 0.020 Uiso 1 1 calc R . . C9 C 0.6179(2) 0.79815(15) 0.16993(13) 0.0127(4) Uani 1 1 d . . . C10 C 0.5894(2) 0.83944(15) 0.33522(14) 0.0130(4) Uani 1 1 d . . . O10 O 0.53558(17) 0.92170(9) 0.36726(10) 0.0166(3) Uani 1 1 d . . . N11 N 0.7158(2) 0.79465(12) 0.37019(11) 0.0129(4) Uani 1 1 d . . . C12 C 0.8025(3) 0.84808(14) 0.44289(14) 0.0162(5) Uani 1 1 d . . . H12A H 0.7290 0.8665 0.4926 0.019 Uiso 1 1 calc R . . C13 C 0.9168(3) 0.76271(17) 0.47507(14) 0.0221(6) Uani 1 1 d . . . H13A H 1.0147 0.7944 0.4977 0.026 Uiso 1 1 calc R . . H13B H 0.8695 0.7198 0.5233 0.026 Uiso 1 1 calc R . . C14 C 0.9478(3) 0.69620(16) 0.39147(15) 0.0200(5) Uani 1 1 d . . . H14A H 1.0306 0.7279 0.3539 0.024 Uiso 1 1 calc R . . H14B H 0.9794 0.6241 0.4081 0.024 Uiso 1 1 calc R . . C15 C 0.7917(2) 0.69588(15) 0.34226(14) 0.0171(5) Uani 1 1 d . . . H15A H 0.8075 0.6943 0.2765 0.021 Uiso 1 1 calc R . . H15B H 0.7280 0.6345 0.3600 0.021 Uiso 1 1 calc R . . C16 C 0.8801(3) 0.94701(17) 0.40799(15) 0.0219(5) Uani 1 1 d . . . H16A H 0.7995 0.9984 0.3898 0.026 Uiso 1 1 calc R . . H16B H 0.9443 0.9790 0.4560 0.026 Uiso 1 1 calc R . . O17 O 0.97596(19) 0.92195(11) 0.33335(11) 0.0262(4) Uani 1 1 d . . . C18 C 1.0160(3) 1.01113(17) 0.28225(19) 0.0315(6) Uani 1 1 d . . . H18A H 1.0815 0.9899 0.2315 0.047 Uiso 1 1 calc R . . H18B H 1.0735 1.0608 0.3200 0.047 Uiso 1 1 calc R . . H18C H 0.9208 1.0446 0.2598 0.047 Uiso 1 1 calc R . . C19 C 0.3545(3) 0.84602(16) 0.23404(15) 0.0216(5) Uani 1 1 d . . . H19A H 0.3051 0.8155 0.1808 0.032 Uiso 1 1 calc R . . H19B H 0.3712 0.9212 0.2245 0.032 Uiso 1 1 calc R . . H19C H 0.2866 0.8357 0.2862 0.032 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 C1 0.0147(11) 0.0153(10) 0.0123(11) 0.0021(8) -0.0006(10) 0.0002(8) C2 0.0133(12) 0.0196(11) 0.0139(11) 0.0016(8) -0.0025(10) -0.0010(9) O2 0.0278(10) 0.0213(8) 0.0164(8) 0.0010(6) 0.0059(8) -0.0072(7) N3 0.0156(10) 0.0151(9) 0.0130(9) -0.0005(7) 0.0020(8) -0.0026(7) C4 0.0083(11) 0.0159(10) 0.0119(11) 0.0017(8) -0.0043(9) -0.0005(8) C5 0.0154(11) 0.0179(10) 0.0138(11) -0.0050(8) -0.0015(10) 0.0021(8) Br5 0.02362(12) 0.01856(11) 0.01864(12) -0.00566(9) 0.00381(13) -0.00066(7) C6 0.0167(12) 0.0237(11) 0.0151(14) 0.0004(8) 0.0053(10) -0.0024(8) C7 0.0218(13) 0.0218(11) 0.0178(11) 0.0054(9) 0.0025(11) -0.0049(9) C8 0.0220(13) 0.0132(9) 0.0156(11) 0.0004(8) -0.0015(11) 0.0013(8) C9 0.0129(12) 0.0164(10) 0.0089(11) 0.0016(8) -0.0026(9) 0.0037(8) C10 0.0153(12) 0.0144(10) 0.0093(11) 0.0018(8) 0.0039(9) -0.0030(8) O10 0.0219(9) 0.0130(7) 0.0148(8) 0.0010(6) 0.0026(7) 0.0049(6) N11 0.0150(9) 0.0134(8) 0.0103(9) 0.0012(6) -0.0008(8) 0.0013(7) C12 0.0175(13) 0.0192(10) 0.0119(11) -0.0022(8) -0.0004(10) 0.0002(9) C13 0.0219(13) 0.0259(12) 0.0184(15) -0.0009(8) -0.0067(10) 0.0024(9) C14 0.0204(13) 0.0193(11) 0.0205(13) 0.0023(9) -0.0010(10) 0.0059(9) C15 0.0195(12) 0.0128(9) 0.0191(12) -0.0035(8) -0.0032(11) 0.0060(9) C16 0.0194(13) 0.0236(11) 0.0226(13) -0.0034(9) 0.0003(10) -0.0033(10) O17 0.0254(10) 0.0223(8) 0.0310(10) 0.0053(6) 0.0116(9) -0.0015(7) C18 0.0287(15) 0.0301(13) 0.0358(16) 0.0117(10) -0.0001(14) -0.0057(11) C19 0.0186(13) 0.0271(12) 0.0190(12) 0.0003(9) -0.0017(11) 0.0034(9) _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 C9 1.509(3) . ? C1 C19 1.535(3) . ? C1 C10 1.545(3) . ? C1 C2 1.556(3) . ? C2 O2 1.219(2) . ? C2 N3 1.368(3) . ? N3 C4 1.398(3) . ? N3 H3N 0.9799(10) . ? C4 C5 1.374(3) . ? C4 C9 1.403(3) . ? C5 C6 1.393(3) . ? C5 Br5 1.9032(18) . ? C6 C7 1.374(3) . ? C6 H6A 0.9500 . ? C7 C8 1.403(3) . ? C7 H7A 0.9500 . ? C8 C9 1.380(3) . ? C8 H8A 0.9500 . ? C10 O10 1.241(2) . ? C10 N11 1.331(3) . ? N11 C15 1.477(2) . ? N11 C12 1.479(3) . ? C12 C16 1.518(3) . ? C12 C13 1.540(3) . ? C12 H12A 1.0000 . ? C13 C14 1.530(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.525(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O17 1.419(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? O17 C18 1.411(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 C9 C1 C19 112.10(17) . . ? C9 C1 C10 111.89(17) . . ? C19 C1 C10 109.53(17) . . ? C9 C1 C2 101.78(16) . . ? C19 C1 C2 106.22(18) . . ? C10 C1 C2 115.06(16) . . ? O2 C2 N3 126.24(18) . . ? O2 C2 C1 126.12(19) . . ? N3 C2 C1 107.54(16) . . ? C2 N3 C4 111.77(16) . . ? C2 N3 H3N 124.5(16) . . ? C4 N3 H3N 123.7(16) . . ? C5 C4 N3 130.10(17) . . ? C5 C4 C9 120.22(17) . . ? N3 C4 C9 109.66(17) . . ? C4 C5 C6 119.41(17) . . ? C4 C5 Br5 120.06(15) . . ? C6 C5 Br5 120.53(16) . . ? C7 C6 C5 120.34(19) . . ? C7 C6 H6A 119.8 . . ? C5 C6 H6A 119.8 . . ? C6 C7 C8 120.99(18) . . ? C6 C7 H7A 119.5 . . ? C8 C7 H7A 119.5 . . ? C9 C8 C7 118.28(18) . . ? C9 C8 H8A 120.9 . . ? C7 C8 H8A 120.9 . . ? C8 C9 C4 120.75(19) . . ? C8 C9 C1 130.50(17) . . ? C4 C9 C1 108.75(17) . . ? O10 C10 N11 120.95(18) . . ? O10 C10 C1 118.95(18) . . ? N11 C10 C1 120.03(17) . . ? C10 N11 C15 127.86(17) . . ? C10 N11 C12 119.84(16) . . ? C15 N11 C12 112.22(16) . . ? N11 C12 C16 110.59(17) . . ? N11 C12 C13 102.80(15) . . ? C16 C12 C13 114.54(18) . . ? N11 C12 H12A 109.6 . . ? C16 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? C14 C13 C12 104.39(17) . . ? C14 C13 H13A 110.9 . . ? C12 C13 H13A 110.9 . . ? C14 C13 H13B 110.9 . . ? C12 C13 H13B 110.9 . . ? H13A C13 H13B 108.9 . . ? C15 C14 C13 103.93(17) . . ? C15 C14 H14A 111.0 . . ? C13 C14 H14A 111.0 . . ? C15 C14 H14B 111.0 . . ? C13 C14 H14B 111.0 . . ? H14A C14 H14B 109.0 . . ? N11 C15 C14 104.36(16) . . ? N11 C15 H15A 110.9 . . ? C14 C15 H15A 110.9 . . ? N11 C15 H15B 110.9 . . ? C14 C15 H15B 110.9 . . ? H15A C15 H15B 108.9 . . ? O17 C16 C12 109.58(17) . . ? O17 C16 H16A 109.8 . . ? C12 C16 H16A 109.8 . . ? O17 C16 H16B 109.8 . . ? C12 C16 H16B 109.8 . . ? H16A C16 H16B 108.2 . . ? C18 O17 C16 112.47(17) . . ? O17 C18 H18A 109.5 . . ? O17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C1 C19 H19A 109.5 . . ? C1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 C1 C2 O2 176.5(2) . . . . ? C19 C1 C2 O2 -66.1(3) . . . . ? C10 C1 C2 O2 55.3(3) . . . . ? C9 C1 C2 N3 -7.0(2) . . . . ? C19 C1 C2 N3 110.42(19) . . . . ? C10 C1 C2 N3 -128.22(19) . . . . ? O2 C2 N3 C4 -177.1(2) . . . . ? C1 C2 N3 C4 6.4(2) . . . . ? C2 N3 C4 C5 175.4(2) . . . . ? C2 N3 C4 C9 -3.0(2) . . . . ? N3 C4 C5 C6 -176.7(2) . . . . ? C9 C4 C5 C6 1.6(3) . . . . ? N3 C4 C5 Br5 3.0(3) . . . . ? C9 C4 C5 Br5 -178.70(15) . . . . ? C4 C5 C6 C7 -1.4(3) . . . . ? Br5 C5 C6 C7 178.97(17) . . . . ? C5 C6 C7 C8 0.2(3) . . . . ? C6 C7 C8 C9 0.8(3) . . . . ? C7 C8 C9 C4 -0.5(3) . . . . ? C7 C8 C9 C1 179.3(2) . . . . ? C5 C4 C9 C8 -0.7(3) . . . . ? N3 C4 C9 C8 177.91(19) . . . . ? C5 C4 C9 C1 179.44(18) . . . . ? N3 C4 C9 C1 -1.9(2) . . . . ? C19 C1 C9 C8 72.4(3) . . . . ? C10 C1 C9 C8 -51.1(3) . . . . ? C2 C1 C9 C8 -174.5(2) . . . . ? C19 C1 C9 C4 -107.78(19) . . . . ? C10 C1 C9 C4 128.71(18) . . . . ? C2 C1 C9 C4 5.3(2) . . . . ? C9 C1 C10 O10 112.2(2) . . . . ? C19 C1 C10 O10 -12.8(3) . . . . ? C2 C1 C10 O10 -132.3(2) . . . . ? C9 C1 C10 N11 -64.9(2) . . . . ? C19 C1 C10 N11 170.20(18) . . . . ? C2 C1 C10 N11 50.7(3) . . . . ? O10 C10 N11 C15 177.98(19) . . . . ? C1 C10 N11 C15 -5.0(3) . . . . ? O10 C10 N11 C12 -5.6(3) . . . . ? C1 C10 N11 C12 171.35(17) . . . . ? C10 N11 C12 C16 -67.6(2) . . . . ? C15 N11 C12 C16 109.29(19) . . . . ? C10 N11 C12 C13 169.67(17) . . . . ? C15 N11 C12 C13 -13.4(2) . . . . ? N11 C12 C13 C14 29.8(2) . . . . ? C16 C12 C13 C14 -90.2(2) . . . . ? C12 C13 C14 C15 -35.6(2) . . . . ? C10 N11 C15 C14 168.16(18) . . . . ? C12 N11 C15 C14 -8.5(2) . . . . ? C13 C14 C15 N11 27.0(2) . . . . ? N11 C12 C16 O17 -55.1(2) . . . . ? C13 C12 C16 O17 60.5(2) . . . . ? C12 C16 O17 C18 163.13(19) . . . . ? 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 N3 H3N O10 0.9799(10) 1.820(5) 2.790(2) 170(2) 3_645 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.589 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.048