data_p26zas _audit_creation_method SHELXL-97 _audit_update_record ; 2004-01-02 text and data added, srw ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C25 H30 Br N O4), C4 H8 O2' _chemical_formula_sum 'C54 H68 Br2 N2 O10' _chemical_formula_structural ? _chemical_formula_weight 1064.92 _chemical_absolute_configuration ad _chemical_formula_analytical ? _chemical_compound_source ? 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 'Monoclinic' _symmetry_space_group_name_H-M 'P 21 ' _symmetry_space_group_name_Hall 'P 2yb ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.4713(18) _cell_length_b 27.311(7) _cell_length_c 14.938(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.220(5) _cell_angle_gamma 90.00 _cell_volume 2640.0(12) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 19.2 _exptl_crystal_description 'columnar' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method ? _exptl_crystal_F_000 1112 _exptl_crystal_id p26zas _exptl_crystal_preparation ; The data crystal was mounted using oil (Parantone-N, Exxon) to a 0.4 mm cryo-loop (Hampton Research) with the (0 1 -1) scattering planes roughly normal to the spindle axis. ; _exptl_absorpt_coefficient_mu 1.593 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.5935 _exptl_absorpt_correction_T_max 0.9185 _exptl_absorpt_process_details '(Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id p26zas _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type ? _diffrn_measurement_device 'Siemens Platform/CCD' _diffrn_measurement_method 'profile data from \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 65 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 306 _diffrn_standards_decay_% 3.6 _diffrn_reflns_number 27759 _diffrn_reflns_av_R_equivalents 0.0930 _diffrn_reflns_av_sigmaI/netI 0.1116 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 21.99 _reflns_number_total 6471 _reflns_number_gt 4437 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT V6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT V6.22 (Bruker, 2001)' _computing_structure_solution 'SHELXTL V6.10 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL V6.10 (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL V6.10 (Bruker, 2001)' _computing_publication_material 'CIFTAB (Sheldrick, 2001)' _refine_special_details ; ? ; _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^)+(0.0892P)^2^+13.9497P] 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 noref _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 0.09(2) _refine_ls_number_reflns 6471 _refine_ls_number_parameters 767 _refine_ls_number_restraints 721 _refine_ls_R_factor_all 0.1305 _refine_ls_R_factor_gt 0.0889 _refine_ls_wR_factor_ref 0.2340 _refine_ls_wR_factor_gt 0.2126 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 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 0.4326(3) 0.67620(11) 0.71956(12) 0.0859(6) Uani 1 1 d . . . C1 C 0.6002(18) 0.8102(5) 0.6240(8) 0.042(3) Uani 1 1 d . . . H1A H 0.5339 0.8350 0.5897 0.051 Uiso 1 1 calc R . . C2 C 0.491(2) 0.7690(5) 0.6459(9) 0.043(3) Uani 1 1 d . . . H2A H 0.3495 0.7662 0.6294 0.052 Uiso 1 1 calc R . . C3 C 0.585(2) 0.7324(6) 0.6907(9) 0.058(4) Uani 1 1 d . . . C4 C 0.795(2) 0.7349(5) 0.7175(8) 0.047(4) Uani 1 1 d . . . H4A H 0.8618 0.7090 0.7489 0.056 Uiso 1 1 calc R . . C5 C 0.896(2) 0.7771(6) 0.6951(9) 0.047(4) Uani 1 1 d . . . H5A H 1.0381 0.7793 0.7111 0.057 Uiso 1 1 calc R . . C6 C 0.810(2) 0.8173(5) 0.6508(8) 0.050(4) Uani 1 1 d . . . C7 C 0.9208(17) 0.8643(5) 0.6283(9) 0.045(4) Uani 1 1 d . . . H7A H 0.8733 0.8763 0.5684 0.054 Uiso 1 1 calc R . . C8 C 0.8841(18) 0.9038(5) 0.6979(8) 0.042(3) Uani 1 1 d . . . H8A H 0.9614 0.9338 0.6793 0.051 Uiso 1 1 calc R . . C9 C 0.9584(19) 0.8892(6) 0.7947(8) 0.052(4) Uani 1 1 d . . . H9A H 1.0556 0.8613 0.7925 0.062 Uiso 1 1 calc R . . H9B H 1.0275 0.9172 0.8246 0.062 Uiso 1 1 calc R . . C10 C 0.763(2) 0.8753(6) 0.8433(9) 0.066(5) Uani 1 1 d . . . H10A H 0.7312 0.8403 0.8334 0.079 Uiso 1 1 calc R . . H10B H 0.7795 0.8809 0.9084 0.079 Uiso 1 1 calc R . . C11 C 0.5934(19) 0.9068(6) 0.8064(8) 0.048(4) Uani 1 1 d . . . H11A H 0.5790 0.9373 0.8416 0.057 Uiso 1 1 calc R . . H11B H 0.4598 0.8892 0.8065 0.057 Uiso 1 1 calc R . . C12 C 0.6621(17) 0.9177(5) 0.7121(7) 0.031(3) Uani 1 1 d . . . C13 C 0.5402(18) 0.9381(4) 0.6506(8) 0.034(3) Uani 1 1 d . A . H13A H 0.3994 0.9436 0.6655 0.041 Uiso 1 1 calc R . . C14 C 0.7724(16) 0.9875(4) 0.5587(7) 0.041(3) Uani 0.74(4) 1 d PGDU A 1 C15 C 0.7587(17) 1.0286(6) 0.6132(9) 0.042(3) Uani 0.74(4) 1 d PGDU A 1 H15A H 0.6438 1.0325 0.6519 0.050 Uiso 0.74(4) 1 calc PR A 1 C16 C 0.913(2) 1.0640(5) 0.6109(12) 0.042(3) Uani 0.74(4) 1 d PGDU A 1 H16A H 0.9036 1.0921 0.6482 0.051 Uiso 0.74(4) 1 calc PR A 1 C17 C 1.0811(16) 1.0582(4) 0.5543(10) 0.046(2) Uani 0.74(4) 1 d PGDU A 1 C18 C 1.0949(17) 1.0171(5) 0.4998(8) 0.041(2) Uani 0.74(4) 1 d PGDU A 1 H18A H 1.2097 1.0132 0.4610 0.049 Uiso 0.74(4) 1 calc PR A 1 C19 C 0.941(2) 0.9818(4) 0.5020(8) 0.041(2) Uani 0.74(4) 1 d PGDU A 1 H19A H 0.9499 0.9537 0.4647 0.049 Uiso 0.74(4) 1 calc PR A 1 C20 C 0.495(2) 0.9355(5) 0.4915(9) 0.039(3) Uani 1 1 d . A . C21 C 0.506(2) 0.9306(5) 0.3271(8) 0.050(4) Uani 1 1 d . A . C22 C 0.2783(19) 0.9307(6) 0.3102(9) 0.056(4) Uani 1 1 d . . . H22A H 0.2278 0.9645 0.3094 0.084 Uiso 1 1 calc R . . H22B H 0.2084 0.9125 0.3578 0.084 Uiso 1 1 calc R . . H22C H 0.2493 0.9152 0.2523 0.084 Uiso 1 1 calc R . . C23 C 0.600(2) 0.8797(6) 0.3290(10) 0.069(4) Uani 1 1 d . . . H23A H 0.5698 0.8630 0.2724 0.103 Uiso 1 1 calc R . . H23B H 0.5407 0.8610 0.3787 0.103 Uiso 1 1 calc R . . H23C H 0.7498 0.8823 0.3371 0.103 Uiso 1 1 calc R . . C24 C 0.609(2) 0.9653(6) 0.2603(8) 0.059(4) Uani 1 1 d . . . H24A H 0.5401 0.9972 0.2620 0.088 Uiso 1 1 calc R . . H24B H 0.5983 0.9516 0.1998 0.088 Uiso 1 1 calc R . . H24C H 0.7553 0.9694 0.2762 0.088 Uiso 1 1 calc R . . C25 C 1.366(3) 1.0985(8) 0.4754(12) 0.054(4) Uani 0.74(4) 1 d PDU A 1 H25A H 1.4570 1.1269 0.4822 0.082 Uiso 0.74(4) 1 calc PR A 1 H25B H 1.2801 1.1026 0.4216 0.082 Uiso 0.74(4) 1 calc PR A 1 H25C H 1.4489 1.0687 0.4698 0.082 Uiso 0.74(4) 1 calc PR A 1 N1 N 0.6084(14) 0.9521(3) 0.5638(6) 0.043(3) Uani 1 1 d D . . O1 O 1.1332(13) 0.8515(4) 0.6238(6) 0.058(3) Uani 1 1 d . . . H1B H 1.1921 0.8690 0.5854 0.086 Uiso 1 1 calc R . . O2 O 1.231(2) 1.0945(5) 0.5549(9) 0.052(3) Uani 0.74(4) 1 d PDU A 1 O3 O 0.5557(12) 0.9554(3) 0.4149(5) 0.041(2) Uani 1 1 d . . . O4 O 0.3661(13) 0.9052(4) 0.4994(5) 0.045(2) Uani 1 1 d . . . Br2 Br -0.0880(3) 0.98341(10) 0.01493(13) 0.0840(6) Uani 1 1 d . . . C26 C 0.0899(19) 0.8504(5) 0.1191(9) 0.046(3) Uani 1 1 d . . . H26A H 0.0271 0.8264 0.1562 0.055 Uiso 1 1 calc R . . C27 C -0.0247(19) 0.8924(5) 0.0918(8) 0.043(3) Uani 1 1 d . . . H27A H -0.1661 0.8953 0.1078 0.051 Uiso 1 1 calc R . . C28 C 0.063(2) 0.9268(5) 0.0452(9) 0.050(4) Uani 1 1 d . . . C29 C 0.272(2) 0.9218(6) 0.0226(8) 0.054(4) Uani 1 1 d . . . H29A H 0.3390 0.9476 -0.0083 0.064 Uiso 1 1 calc R . . C30 C 0.3776(19) 0.8815(5) 0.0436(8) 0.035(3) Uani 1 1 d . . . H30A H 0.5169 0.8787 0.0244 0.042 Uiso 1 1 calc R . . C31 C 0.2934(18) 0.8443(5) 0.0915(7) 0.038(3) Uani 1 1 d . . . C32 C 0.4038(17) 0.7986(5) 0.1131(9) 0.039(3) Uani 1 1 d . . . H32A H 0.3522 0.7873 0.1726 0.047 Uiso 1 1 calc R . . C33 C 0.3814(16) 0.7546(5) 0.0473(8) 0.035(3) Uani 1 1 d . . . H33A H 0.4600 0.7258 0.0711 0.042 Uiso 1 1 calc R . . C34 C 0.4573(19) 0.7667(5) -0.0477(8) 0.043(3) Uani 1 1 d . . . H34A H 0.5599 0.7936 -0.0460 0.051 Uiso 1 1 calc R . . H34B H 0.5218 0.7376 -0.0756 0.051 Uiso 1 1 calc R . . C35 C 0.264(2) 0.7823(7) -0.1003(10) 0.080(5) Uani 1 1 d . . . H35A H 0.2372 0.8177 -0.0921 0.096 Uiso 1 1 calc R . . H35B H 0.2818 0.7757 -0.1650 0.096 Uiso 1 1 calc R . . C36 C 0.089(2) 0.7521(6) -0.0623(9) 0.056(4) Uani 1 1 d . . . H36A H 0.0704 0.7217 -0.0975 0.067 Uiso 1 1 calc R . . H36B H -0.0416 0.7708 -0.0638 0.067 Uiso 1 1 calc R . . C37 C 0.150(2) 0.7400(5) 0.0335(9) 0.047(4) Uani 1 1 d . . . C38 C 0.030(2) 0.7207(4) 0.0921(9) 0.041(3) Uani 1 1 d . B . H38A H -0.1094 0.7151 0.0754 0.049 Uiso 1 1 calc R . . C39 C 0.225(2) 0.6646(4) 0.1895(8) 0.040(3) Uani 0.561(10) 1 d PGDU B 1 C40 C 0.1512(18) 0.6215(6) 0.1518(10) 0.046(3) Uani 0.561(10) 1 d PGDU B 1 H40 H 0.0193 0.6209 0.1237 0.055 Uiso 0.561(10) 1 calc PR B 1 C41 C 0.270(2) 0.5791(4) 0.1552(11) 0.048(3) Uani 0.561(10) 1 d PGU B 1 H41 H 0.2195 0.5496 0.1294 0.058 Uiso 0.561(10) 1 calc PR B 1 C42 C 0.463(2) 0.5799(4) 0.1963(11) 0.051(3) Uani 0.561(10) 1 d PGDU B 1 C43 C 0.5372(19) 0.6230(5) 0.2341(12) 0.045(3) Uani 0.561(10) 1 d PGU B 1 H43 H 0.6691 0.6235 0.2622 0.054 Uiso 0.561(10) 1 calc PR B 1 C44 C 0.418(3) 0.6654(4) 0.2306(11) 0.037(3) Uani 0.561(10) 1 d PGDU B 1 H44 H 0.4690 0.6948 0.2564 0.044 Uiso 0.561(10) 1 calc PR B 1 C45 C -0.011(2) 0.7255(5) 0.2506(8) 0.036(3) Uani 1 1 d . B . C46 C -0.003(2) 0.7308(5) 0.4144(8) 0.053(4) Uani 1 1 d . B . C47 C -0.229(2) 0.7285(6) 0.4295(10) 0.062(4) Uani 1 1 d . . . H47A H -0.2731 0.6942 0.4319 0.093 Uiso 1 1 calc R . . H47B H -0.3010 0.7451 0.3803 0.093 Uiso 1 1 calc R . . H47C H -0.2624 0.7447 0.4862 0.093 Uiso 1 1 calc R . . C48 C 0.075(2) 0.7837(6) 0.4110(11) 0.071(5) Uani 1 1 d . . . H48A H -0.0033 0.8020 0.3659 0.106 Uiso 1 1 calc R . . H48B H 0.2221 0.7838 0.3951 0.106 Uiso 1 1 calc R . . H48C H 0.0575 0.7991 0.4697 0.106 Uiso 1 1 calc R . . C49 C 0.120(2) 0.7001(6) 0.4820(10) 0.064(4) Uani 1 1 d . . . H49A H 0.0652 0.6666 0.4828 0.097 Uiso 1 1 calc R . . H49B H 0.1066 0.7146 0.5417 0.097 Uiso 1 1 calc R . . H49C H 0.2654 0.6995 0.4647 0.097 Uiso 1 1 calc R . . C50 C 0.782(3) 0.5332(9) 0.2218(19) 0.064(4) Uani 0.561(10) 1 d PDU B 1 H50A H 0.8392 0.5008 0.2086 0.096 Uiso 0.561(10) 1 calc PR B 1 H50B H 0.7755 0.5378 0.2868 0.096 Uiso 0.561(10) 1 calc PR B 1 H50C H 0.8707 0.5584 0.1956 0.096 Uiso 0.561(10) 1 calc PR B 1 N2 N 0.0937(12) 0.7066(3) 0.1829(6) 0.027(2) Uani 1 1 d D . . O5 O 0.6185(12) 0.8107(3) 0.1244(6) 0.059(3) Uani 1 1 d . . . H5B H 0.6722 0.7916 0.1620 0.089 Uiso 1 1 calc R . . O6 O 0.572(2) 0.5370(4) 0.1833(11) 0.062(3) Uani 0.561(10) 1 d PDU B 1 O7 O 0.0517(12) 0.7067(3) 0.3276(5) 0.041(2) Uani 1 1 d . . . O8 O -0.1465(13) 0.7562(4) 0.2431(6) 0.053(3) Uani 1 1 d . . . C51 C 0.731(9) 0.5932(16) 0.895(5) 0.334(14) Uani 0.67(2) 1 d PDU C 1 C52 C 0.666(11) 0.6339(15) 0.954(4) 0.333(14) Uani 0.67(2) 1 d PDU C 1 H52A H 0.7796 0.6574 0.9604 0.500 Uiso 0.67(2) 1 calc PR C 1 H52B H 0.6299 0.6209 1.0133 0.500 Uiso 0.67(2) 1 calc PR C 1 H52C H 0.5455 0.6504 0.9281 0.500 Uiso 0.67(2) 1 calc PR C 1 C53 C 0.884(8) 0.5664(19) 0.769(4) 0.333(14) Uani 0.67(2) 1 d PDU C 1 H53A H 0.7482 0.5706 0.7395 0.399 Uiso 0.67(2) 1 calc PR C 1 H53B H 0.8975 0.5317 0.7878 0.399 Uiso 0.67(2) 1 calc PR C 1 C54 C 1.055(11) 0.5790(19) 0.704(4) 0.331(14) Uani 0.67(2) 1 d PDU C 1 H54A H 1.0337 0.5611 0.6475 0.496 Uiso 0.67(2) 1 calc PR C 1 H54B H 1.1892 0.5698 0.7295 0.496 Uiso 0.67(2) 1 calc PR C 1 H54C H 1.0536 0.6143 0.6916 0.496 Uiso 0.67(2) 1 calc PR C 1 O9 O 0.898(6) 0.5977(15) 0.845(3) 0.333(14) Uani 0.67(2) 1 d PDU C 1 O10 O 0.617(7) 0.5568(12) 0.888(3) 0.335(14) Uani 0.67(2) 1 d PDU C 1 C55 C 0.857(15) 0.595(3) 0.835(6) 0.333(14) Uani 0.33(2) 1 d PDU C 2 C56 C 1.052(18) 0.575(4) 0.801(9) 0.332(14) Uani 0.33(2) 1 d PDU C 2 H56A H 1.0574 0.5789 0.7356 0.499 Uiso 0.33(2) 1 calc PR C 2 H56B H 1.0591 0.5397 0.8153 0.499 Uiso 0.33(2) 1 calc PR C 2 H56C H 1.1695 0.5917 0.8284 0.499 Uiso 0.33(2) 1 calc PR C 2 C57 C 0.681(18) 0.615(4) 0.960(6) 0.333(14) Uani 0.33(2) 1 d PDU C 2 H57A H 0.7391 0.6474 0.9422 0.400 Uiso 0.33(2) 1 calc PR C 2 H57B H 0.7123 0.6103 1.0246 0.400 Uiso 0.33(2) 1 calc PR C 2 C58 C 0.449(18) 0.615(4) 0.946(10) 0.333(15) Uani 0.33(2) 1 d PDU C 2 H58A H 0.3828 0.6358 0.9914 0.500 Uiso 0.33(2) 1 calc PR C 2 H58B H 0.3962 0.5818 0.9504 0.500 Uiso 0.33(2) 1 calc PR C 2 H58C H 0.4171 0.6284 0.8862 0.500 Uiso 0.33(2) 1 calc PR C 2 O11 O 0.772(16) 0.577(3) 0.908(7) 0.334(14) Uani 0.33(2) 1 d PDU C 2 O12 O 0.792(16) 0.635(2) 0.803(6) 0.334(14) Uani 0.33(2) 1 d PDU C 2 C59 C 0.249(2) 0.6694(6) 0.1894(12) 0.040(3) Uani 0.439(10) 1 d PGDU B 2 C60 C 0.416(3) 0.6778(5) 0.2460(13) 0.035(3) Uani 0.439(10) 1 d PGDU B 2 H60 H 0.4247 0.7075 0.2790 0.041 Uiso 0.439(10) 1 calc PR B 2 C61 C 0.571(3) 0.6428(7) 0.2545(14) 0.043(3) Uani 0.439(10) 1 d PGU B 2 H61 H 0.6853 0.6486 0.2932 0.051 Uiso 0.439(10) 1 calc PR B 2 C62 C 0.559(2) 0.5994(6) 0.2062(13) 0.049(3) Uani 0.439(10) 1 d PGDU B 2 C63 C 0.392(3) 0.5909(6) 0.1496(13) 0.050(3) Uani 0.439(10) 1 d PGU B 2 H63 H 0.3832 0.5613 0.1166 0.059 Uiso 0.439(10) 1 calc PR B 2 C64 C 0.237(2) 0.6259(7) 0.1411(13) 0.046(3) Uani 0.439(10) 1 d PGDU B 2 H64 H 0.1227 0.6202 0.1024 0.055 Uiso 0.439(10) 1 calc PR B 2 C65 C 0.711(5) 0.5199(8) 0.165(2) 0.066(4) Uani 0.439(10) 1 d PDU B 2 H65A H 0.8360 0.5008 0.1782 0.098 Uiso 0.439(10) 1 calc PR B 2 H65B H 0.7050 0.5272 0.1010 0.098 Uiso 0.439(10) 1 calc PR B 2 H65C H 0.5890 0.5010 0.1824 0.098 Uiso 0.439(10) 1 calc PR B 2 O13 O 0.717(3) 0.5661(6) 0.2162(14) 0.064(3) Uani 0.439(10) 1 d PDU B 2 C66 C 0.741(5) 0.9944(11) 0.5604(16) 0.041(3) Uani 0.26(4) 1 d PGDU A 2 C67 C 0.719(5) 1.0423(14) 0.591(3) 0.042(3) Uani 0.26(4) 1 d PGDU A 2 H67A H 0.5967 1.0521 0.6203 0.051 Uiso 0.26(4) 1 calc PR A 2 C68 C 0.878(6) 1.0759(10) 0.577(3) 0.043(3) Uani 0.26(4) 1 d PGDU A 2 H68A H 0.8631 1.1086 0.5978 0.052 Uiso 0.26(4) 1 calc PR A 2 C69 C 1.057(5) 1.0616(12) 0.534(3) 0.045(3) Uani 0.26(4) 1 d PGDU A 2 C70 C 1.079(5) 1.0137(15) 0.503(3) 0.043(3) Uani 0.26(4) 1 d PGDU A 2 H70A H 1.2014 1.0039 0.4737 0.051 Uiso 0.26(4) 1 calc PR A 2 C71 C 0.920(7) 0.9801(9) 0.517(2) 0.041(3) Uani 0.26(4) 1 d PGDU A 2 H71A H 0.9349 0.9474 0.4963 0.049 Uiso 0.26(4) 1 calc PR A 2 C72 C 1.407(4) 1.094(2) 0.506(5) 0.052(4) Uani 0.26(4) 1 d PDU A 2 H72A H 1.4839 1.1244 0.5148 0.079 Uiso 0.26(4) 1 calc PR A 2 H72B H 1.4174 1.0834 0.4438 0.079 Uiso 0.26(4) 1 calc PR A 2 H72C H 1.4652 1.0684 0.5454 0.079 Uiso 0.26(4) 1 calc PR A 2 O14 O 1.187(5) 1.1017(9) 0.529(3) 0.051(3) Uani 0.26(4) 1 d PDU A 2 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 0.0823(13) 0.0790(12) 0.0963(13) 0.0062(11) 0.0061(10) -0.0265(11) C1 0.023(7) 0.068(10) 0.036(8) -0.005(7) -0.003(6) 0.006(7) C2 0.037(8) 0.049(9) 0.043(8) -0.005(7) -0.008(7) -0.006(7) C3 0.042(9) 0.101(13) 0.032(8) 0.015(9) 0.002(7) -0.021(9) C4 0.060(10) 0.043(9) 0.038(8) 0.003(7) -0.013(7) -0.013(7) C5 0.025(7) 0.076(11) 0.041(8) 0.009(8) -0.007(6) 0.013(7) C6 0.051(9) 0.065(10) 0.033(8) 0.002(7) -0.003(7) 0.008(8) C7 0.016(7) 0.055(9) 0.064(9) -0.005(8) 0.021(6) -0.001(6) C8 0.028(7) 0.054(8) 0.044(8) 0.005(7) -0.018(6) -0.010(6) C9 0.038(8) 0.093(12) 0.025(7) -0.017(7) 0.006(6) -0.002(8) C10 0.043(9) 0.117(13) 0.038(8) 0.039(9) -0.008(7) 0.002(9) C11 0.037(8) 0.078(10) 0.028(7) -0.002(7) 0.005(6) 0.002(7) C12 0.022(7) 0.044(8) 0.028(7) -0.003(6) 0.001(6) 0.006(6) C13 0.021(7) 0.042(8) 0.039(8) 0.004(6) 0.000(6) 0.003(6) C14 0.041(5) 0.033(5) 0.048(5) 0.001(5) 0.002(4) 0.001(5) C15 0.040(5) 0.034(5) 0.051(6) 0.000(5) -0.004(5) 0.009(5) C16 0.044(5) 0.033(5) 0.050(6) -0.004(5) -0.008(5) 0.006(5) C17 0.043(5) 0.039(4) 0.054(5) 0.001(4) -0.009(4) 0.000(4) C18 0.036(5) 0.037(5) 0.050(5) 0.004(4) -0.003(4) 0.001(4) C19 0.033(5) 0.032(5) 0.057(5) 0.001(5) 0.004(4) 0.004(4) C20 0.019(7) 0.062(10) 0.037(8) -0.005(7) -0.001(6) -0.005(7) C21 0.048(9) 0.071(11) 0.031(8) -0.018(7) -0.020(6) 0.010(8) C22 0.037(9) 0.086(11) 0.046(8) -0.015(8) -0.001(7) -0.008(8) C23 0.074(11) 0.077(11) 0.055(10) -0.016(8) 0.010(8) 0.018(9) C24 0.048(9) 0.104(13) 0.025(7) 0.002(7) 0.008(6) -0.002(8) C25 0.048(7) 0.054(6) 0.061(8) 0.002(6) -0.006(6) -0.003(6) N1 0.048(7) 0.062(7) 0.019(6) -0.010(5) -0.002(5) -0.019(6) O1 0.030(5) 0.072(7) 0.070(6) 0.024(5) 0.012(4) 0.013(5) O2 0.049(5) 0.046(5) 0.060(6) -0.001(5) -0.009(4) -0.003(4) O3 0.035(5) 0.050(5) 0.038(5) -0.004(4) 0.007(4) -0.012(4) O4 0.026(5) 0.066(6) 0.044(5) 0.012(5) 0.004(4) 0.000(5) Br2 0.0751(12) 0.0776(12) 0.0995(13) 0.0145(11) 0.0049(9) 0.0244(10) C26 0.028(8) 0.062(10) 0.049(8) -0.010(7) 0.006(6) -0.003(7) C27 0.026(7) 0.063(10) 0.039(8) -0.008(7) -0.008(6) -0.004(7) C28 0.067(11) 0.041(8) 0.043(8) 0.002(7) 0.000(7) -0.005(8) C29 0.058(10) 0.058(10) 0.045(9) 0.020(7) 0.032(7) -0.002(9) C30 0.034(7) 0.046(8) 0.027(7) -0.009(6) 0.015(6) -0.015(7) C31 0.027(8) 0.060(9) 0.027(7) 0.000(7) 0.000(6) -0.004(7) C32 0.013(7) 0.063(10) 0.042(8) 0.014(7) 0.003(5) 0.004(6) C33 0.011(6) 0.063(9) 0.032(7) 0.022(7) 0.008(5) 0.011(6) C34 0.038(8) 0.049(8) 0.041(8) 0.006(7) -0.006(6) -0.004(7) C35 0.064(11) 0.128(15) 0.050(10) 0.023(10) 0.030(9) 0.004(11) C36 0.053(10) 0.079(11) 0.035(8) -0.001(8) -0.022(7) 0.017(8) C37 0.038(8) 0.063(9) 0.039(8) 0.008(7) -0.008(7) 0.008(7) C38 0.044(8) 0.032(7) 0.047(8) 0.017(6) -0.002(7) -0.019(6) C39 0.036(5) 0.037(5) 0.047(6) 0.003(5) 0.013(5) -0.008(5) C40 0.043(6) 0.040(6) 0.055(6) 0.000(6) 0.010(6) -0.007(6) C41 0.048(6) 0.041(6) 0.057(6) -0.003(6) 0.006(6) -0.005(6) C42 0.052(6) 0.039(5) 0.062(6) 0.001(6) 0.006(6) 0.000(5) C43 0.039(6) 0.040(6) 0.056(6) 0.003(5) 0.010(5) -0.004(5) C44 0.029(5) 0.033(5) 0.048(6) 0.007(5) 0.013(5) -0.006(5) C45 0.034(8) 0.059(9) 0.014(7) 0.009(7) -0.009(6) -0.007(7) C46 0.087(12) 0.046(9) 0.024(7) -0.011(7) -0.008(7) 0.008(8) C47 0.040(9) 0.089(12) 0.057(9) 0.005(8) 0.022(7) 0.010(8) C48 0.068(11) 0.061(10) 0.084(12) 0.000(9) 0.016(9) 0.010(9) C49 0.064(10) 0.064(10) 0.065(10) -0.014(8) 0.011(8) -0.005(8) C50 0.070(8) 0.044(8) 0.078(8) 0.008(8) 0.002(7) 0.011(6) N2 0.023(5) 0.032(5) 0.025(6) 0.000(5) -0.003(4) -0.005(4) O5 0.025(5) 0.074(7) 0.078(7) 0.026(6) -0.007(4) -0.013(5) O6 0.069(7) 0.042(6) 0.075(7) 0.003(6) 0.001(6) 0.011(5) O7 0.038(5) 0.053(5) 0.031(5) -0.014(4) 0.005(4) 0.007(4) O8 0.030(5) 0.083(7) 0.048(6) -0.003(5) 0.012(4) 0.031(5) C51 0.46(4) 0.135(18) 0.41(3) 0.118(19) -0.07(3) 0.012(19) C52 0.46(4) 0.136(19) 0.41(3) 0.116(19) -0.07(3) 0.01(2) C53 0.46(4) 0.132(18) 0.41(3) 0.118(19) -0.07(3) 0.01(2) C54 0.45(4) 0.128(19) 0.41(3) 0.12(2) -0.07(3) 0.01(2) O9 0.46(4) 0.133(18) 0.41(3) 0.120(19) -0.07(3) 0.013(19) O10 0.46(4) 0.138(18) 0.41(3) 0.116(19) -0.07(3) 0.010(19) C55 0.46(4) 0.134(18) 0.41(3) 0.119(19) -0.07(3) 0.012(19) C56 0.45(4) 0.132(18) 0.41(3) 0.119(19) -0.07(3) 0.012(19) C57 0.46(4) 0.135(19) 0.41(3) 0.117(19) -0.07(3) 0.01(2) C58 0.46(4) 0.14(2) 0.41(3) 0.12(2) -0.07(3) 0.01(2) O11 0.46(4) 0.135(18) 0.41(3) 0.117(19) -0.07(3) 0.011(19) O12 0.46(4) 0.134(19) 0.41(3) 0.119(19) -0.07(3) 0.01(2) C59 0.037(6) 0.037(5) 0.048(6) 0.003(5) 0.012(5) -0.007(5) C60 0.029(5) 0.031(6) 0.044(6) 0.005(5) 0.015(5) -0.008(5) C61 0.039(6) 0.035(6) 0.055(7) 0.005(6) 0.008(6) -0.007(6) C62 0.046(6) 0.039(6) 0.061(6) 0.001(6) 0.009(5) -0.002(5) C63 0.048(7) 0.042(6) 0.059(7) -0.003(6) 0.010(6) -0.004(6) C64 0.042(6) 0.041(6) 0.054(6) -0.001(5) 0.010(6) -0.007(6) C65 0.071(8) 0.046(7) 0.080(9) 0.003(7) 0.000(8) 0.010(7) O13 0.065(7) 0.046(7) 0.081(7) 0.001(6) 0.005(6) 0.012(5) C66 0.039(6) 0.034(5) 0.051(6) 0.002(5) 0.000(5) 0.004(5) C67 0.042(6) 0.035(6) 0.050(6) 0.001(5) -0.004(5) 0.006(5) C68 0.043(6) 0.035(5) 0.051(6) -0.002(5) -0.008(5) 0.004(5) C69 0.043(5) 0.039(5) 0.053(6) 0.001(5) -0.009(5) 0.001(4) C70 0.038(5) 0.037(5) 0.053(6) 0.002(5) -0.004(5) 0.003(5) C71 0.036(6) 0.033(5) 0.053(6) 0.002(5) 0.001(5) 0.004(5) C72 0.047(7) 0.051(7) 0.060(8) 0.001(7) -0.009(7) -0.003(7) O14 0.047(6) 0.047(5) 0.059(7) 0.001(6) -0.009(6) -0.003(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 Br1 C3 1.875(14) . ? C1 C2 1.371(18) . ? C1 C6 1.427(18) . ? C1 H1A 0.9500 . ? C2 C3 1.346(18) . ? C2 H2A 0.9500 . ? C3 C4 1.421(19) . ? C4 C5 1.367(18) . ? C4 H4A 0.9500 . ? C5 C6 1.397(18) . ? C5 H5A 0.9500 . ? C6 C7 1.508(19) . ? C7 O1 1.420(14) . ? C7 C8 1.518(18) . ? C7 H7A 1.0000 . ? C8 C12 1.502(17) . ? C8 C9 1.573(17) . ? C8 H8A 1.0000 . ? C9 C10 1.508(18) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.499(19) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.508(16) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.331(16) . ? C13 N1 1.424(14) . ? C13 H13A 0.9500 . ? C14 C15 1.3900 . ? C14 C19 1.3900 . ? C14 N1 1.437(9) . ? C15 C16 1.3900 . ? C15 H15A 0.9500 . ? C16 C17 1.3900 . ? C16 H16A 0.9500 . ? C17 O2 1.384(8) . ? C17 C18 1.3900 . ? C18 C19 1.3900 . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 O4 1.180(15) . ? C20 O3 1.327(15) . ? C20 N1 1.381(15) . ? C21 C22 1.495(18) . ? C21 O3 1.509(15) . ? C21 C23 1.515(19) . ? C21 C24 1.533(19) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 O2 1.481(9) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? N1 C66 1.439(11) . ? O1 H1B 0.8400 . ? Br2 C28 1.882(14) . ? C26 C31 1.391(17) . ? C26 C27 1.425(18) . ? C26 H26A 0.9500 . ? C27 C28 1.302(17) . ? C27 H27A 0.9500 . ? C28 C29 1.399(18) . ? C29 C30 1.334(18) . ? C29 H29A 0.9500 . ? C30 C31 1.359(17) . ? C30 H30A 0.9500 . ? C31 C32 1.473(17) . ? C32 O5 1.437(14) . ? C32 C33 1.559(18) . ? C32 H32A 1.0000 . ? C33 C34 1.539(17) . ? C33 C37 1.565(17) . ? C33 H33A 1.0000 . ? C34 C35 1.53(2) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.52(2) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.518(18) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C38 1.282(17) . ? C38 N2 1.468(15) . ? C38 H38A 0.9500 . ? C39 C40 1.3900 . ? C39 C44 1.3900 . ? C39 N2 1.432(9) . ? C40 C41 1.3900 . ? C40 H40 0.9500 . ? C41 C42 1.3900 . ? C41 H41 0.9500 . ? C42 O6 1.381(9) . ? C42 C43 1.3900 . ? C43 C44 1.3900 . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C45 O8 1.219(15) . ? C45 O7 1.321(13) . ? C45 N2 1.322(15) . ? C46 C47 1.48(2) . ? C46 O7 1.499(15) . ? C46 C49 1.531(19) . ? C46 C48 1.53(2) . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? C50 O6 1.477(9) . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? N2 C59 1.433(10) . ? O5 H5B 0.8400 . ? C51 O10 1.241(9) . ? C51 O9 1.321(9) . ? C51 C52 1.481(9) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 O9 1.430(10) . ? C53 C54 1.518(10) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? C55 O12 1.243(14) . ? C55 O11 1.323(13) . ? C55 C56 1.482(14) . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? C57 O11 1.430(14) . ? C57 C58 1.518(14) . ? C57 H57A 0.9900 . ? C57 H57B 0.9900 . ? C58 H58A 0.9800 . ? C58 H58B 0.9800 . ? C58 H58C 0.9800 . ? C59 C60 1.3900 . ? C59 C64 1.3900 . ? C60 C61 1.3900 . ? C60 H60 0.9500 . ? C61 C62 1.3900 . ? C61 H61 0.9500 . ? C62 O13 1.377(9) . ? C62 C63 1.3900 . ? C63 C64 1.3900 . ? C63 H63 0.9500 . ? C64 H64 0.9500 . ? C65 O13 1.474(10) . ? C65 H65A 0.9800 . ? C65 H65B 0.9800 . ? C65 H65C 0.9800 . ? C66 C67 1.3900 . ? C66 C71 1.3900 . ? C67 C68 1.3900 . ? C67 H67A 0.9500 . ? C68 C69 1.3900 . ? C68 H68A 0.9500 . ? C69 O14 1.383(10) . ? C69 C70 1.3900 . ? C70 C71 1.3900 . ? C70 H70A 0.9500 . ? C71 H71A 0.9500 . ? C72 O14 1.481(10) . ? C72 H72A 0.9800 . ? C72 H72B 0.9800 . ? C72 H72C 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 C2 C1 C6 122.4(12) . . ? C2 C1 H1A 118.8 . . ? C6 C1 H1A 118.8 . . ? C3 C2 C1 119.7(12) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? C2 C3 C4 122.4(13) . . ? C2 C3 Br1 119.0(10) . . ? C4 C3 Br1 118.6(11) . . ? C5 C4 C3 115.4(13) . . ? C5 C4 H4A 122.3 . . ? C3 C4 H4A 122.3 . . ? C4 C5 C6 126.1(13) . . ? C4 C5 H5A 116.9 . . ? C6 C5 H5A 116.9 . . ? C5 C6 C1 113.8(13) . . ? C5 C6 C7 125.8(12) . . ? C1 C6 C7 120.3(12) . . ? O1 C7 C6 105.1(10) . . ? O1 C7 C8 111.2(11) . . ? C6 C7 C8 112.1(10) . . ? O1 C7 H7A 109.4 . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? C12 C8 C7 115.4(10) . . ? C12 C8 C9 102.9(10) . . ? C7 C8 C9 113.7(11) . . ? C12 C8 H8A 108.1 . . ? C7 C8 H8A 108.1 . . ? C9 C8 H8A 108.1 . . ? C10 C9 C8 104.6(10) . . ? C10 C9 H9A 110.8 . . ? C8 C9 H9A 110.8 . . ? C10 C9 H9B 110.8 . . ? C8 C9 H9B 110.8 . . ? H9A C9 H9B 108.9 . . ? C11 C10 C9 107.0(11) . . ? C11 C10 H10A 110.3 . . ? C9 C10 H10A 110.3 . . ? C11 C10 H10B 110.3 . . ? C9 C10 H10B 110.3 . . ? H10A C10 H10B 108.6 . . ? C10 C11 C12 103.8(10) . . ? C10 C11 H11A 111.0 . . ? C12 C11 H11A 111.0 . . ? C10 C11 H11B 111.0 . . ? C12 C11 H11B 111.0 . . ? H11A C11 H11B 109.0 . . ? C13 C12 C8 125.0(10) . . ? C13 C12 C11 123.5(10) . . ? C8 C12 C11 111.5(10) . . ? C12 C13 N1 123.8(10) . . ? C12 C13 H13A 118.1 . . ? N1 C13 H13A 118.1 . . ? C15 C14 C19 120.0 . . ? C15 C14 N1 117.5(10) . . ? C19 C14 N1 122.5(10) . . ? C16 C15 C14 120.0 . . ? C16 C15 H15A 120.0 . . ? C14 C15 H15A 120.0 . . ? C15 C16 C17 120.0 . . ? C15 C16 H16A 120.0 . . ? C17 C16 H16A 120.0 . . ? O2 C17 C16 117.7(11) . . ? O2 C17 C18 122.3(11) . . ? C16 C17 C18 120.0 . . ? C19 C18 C17 120.0 . . ? C19 C18 H18A 120.0 . . ? C17 C18 H18A 120.0 . . ? C18 C19 C14 120.0 . . ? C18 C19 H19A 120.0 . . ? C14 C19 H19A 120.0 . . ? O4 C20 O3 125.8(12) . . ? O4 C20 N1 121.7(12) . . ? O3 C20 N1 112.3(11) . . ? C22 C21 O3 110.6(10) . . ? C22 C21 C23 113.6(13) . . ? O3 C21 C23 108.1(10) . . ? C22 C21 C24 108.7(11) . . ? O3 C21 C24 101.3(10) . . ? C23 C21 C24 113.8(12) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O2 C25 H25A 109.5 . . ? O2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C20 N1 C13 117.2(9) . . ? C20 N1 C14 124.8(8) . . ? C13 N1 C14 117.4(8) . . ? C20 N1 C66 123.5(10) . . ? C13 N1 C66 115.8(13) . . ? C7 O1 H1B 109.5 . . ? C17 O2 C25 117.5(10) . . ? C20 O3 C21 120.2(10) . . ? C31 C26 C27 120.3(13) . . ? C31 C26 H26A 119.9 . . ? C27 C26 H26A 119.9 . . ? C28 C27 C26 120.5(12) . . ? C28 C27 H27A 119.7 . . ? C26 C27 H27A 119.7 . . ? C27 C28 C29 118.7(13) . . ? C27 C28 Br2 119.7(11) . . ? C29 C28 Br2 121.5(11) . . ? C30 C29 C28 121.4(12) . . ? C30 C29 H29A 119.3 . . ? C28 C29 H29A 119.3 . . ? C29 C30 C31 122.3(11) . . ? C29 C30 H30A 118.9 . . ? C31 C30 H30A 118.9 . . ? C30 C31 C26 116.6(12) . . ? C30 C31 C32 123.6(11) . . ? C26 C31 C32 119.7(12) . . ? O5 C32 C31 107.4(10) . . ? O5 C32 C33 109.8(9) . . ? C31 C32 C33 118.1(10) . . ? O5 C32 H32A 107.0 . . ? C31 C32 H32A 107.0 . . ? C33 C32 H32A 107.0 . . ? C34 C33 C32 112.7(10) . . ? C34 C33 C37 104.0(9) . . ? C32 C33 C37 111.4(9) . . ? C34 C33 H33A 109.5 . . ? C32 C33 H33A 109.5 . . ? C37 C33 H33A 109.5 . . ? C35 C34 C33 105.7(10) . . ? C35 C34 H34A 110.6 . . ? C33 C34 H34A 110.6 . . ? C35 C34 H34B 110.6 . . ? C33 C34 H34B 110.6 . . ? H34A C34 H34B 108.7 . . ? C36 C35 C34 105.4(12) . . ? C36 C35 H35A 110.7 . . ? C34 C35 H35A 110.7 . . ? C36 C35 H35B 110.7 . . ? C34 C35 H35B 110.7 . . ? H35A C35 H35B 108.8 . . ? C35 C36 C37 106.3(12) . . ? C35 C36 H36A 110.5 . . ? C37 C36 H36A 110.5 . . ? C35 C36 H36B 110.5 . . ? C37 C36 H36B 110.5 . . ? H36A C36 H36B 108.7 . . ? C38 C37 C36 125.4(13) . . ? C38 C37 C33 126.4(11) . . ? C36 C37 C33 108.2(11) . . ? C37 C38 N2 125.0(12) . . ? C37 C38 H38A 117.5 . . ? N2 C38 H38A 117.5 . . ? C40 C39 C44 120.0 . . ? C40 C39 N2 116.6(13) . . ? C44 C39 N2 123.4(13) . . ? C41 C40 C39 120.0 . . ? C41 C40 H40 120.0 . . ? C39 C40 H40 120.0 . . ? C40 C41 C42 120.0 . . ? C40 C41 H41 120.0 . . ? C42 C41 H41 120.0 . . ? O6 C42 C43 126.8(12) . . ? O6 C42 C41 112.6(12) . . ? C43 C42 C41 120.0 . . ? C42 C43 C44 120.0 . . ? C42 C43 H43 120.0 . . ? C44 C43 H43 120.0 . . ? C43 C44 C39 120.0 . . ? C43 C44 H44 120.0 . . ? C39 C44 H44 120.0 . . ? O8 C45 O7 124.4(11) . . ? O8 C45 N2 124.6(10) . . ? O7 C45 N2 111.0(11) . . ? C47 C46 O7 110.5(11) . . ? C47 C46 C49 112.8(12) . . ? O7 C46 C49 101.9(10) . . ? C47 C46 C48 111.9(12) . . ? O7 C46 C48 107.8(11) . . ? C49 C46 C48 111.5(12) . . ? C46 C47 H47A 109.5 . . ? C46 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C46 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C46 C48 H48A 109.5 . . ? C46 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C46 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C46 C49 H49A 109.5 . . ? C46 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C46 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? O6 C50 H50A 109.5 . . ? O6 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? O6 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C45 N2 C39 124.4(8) . . ? C45 N2 C59 125.9(10) . . ? C45 N2 C38 117.6(9) . . ? C39 N2 C38 115.9(9) . . ? C59 N2 C38 116.2(10) . . ? C32 O5 H5B 109.5 . . ? C42 O6 C50 118.4(13) . . ? C45 O7 C46 120.6(10) . . ? O10 C51 O9 120.7(15) . . ? O10 C51 C52 119.0(15) . . ? O9 C51 C52 120.1(15) . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? O9 C53 C54 109.5(15) . . ? O9 C53 H53A 109.8 . . ? C54 C53 H53A 109.8 . . ? O9 C53 H53B 109.8 . . ? C54 C53 H53B 109.8 . . ? H53A C53 H53B 108.2 . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C51 O9 C53 110.3(16) . . ? O12 C55 O11 120(2) . . ? O12 C55 C56 119(2) . . ? O11 C55 C56 119.9(19) . . ? C55 C56 H56A 109.5 . . ? C55 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C55 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? O11 C57 C58 109.5(18) . . ? O11 C57 H57A 109.8 . . ? C58 C57 H57A 109.8 . . ? O11 C57 H57B 109.8 . . ? C58 C57 H57B 109.8 . . ? H57A C57 H57B 108.2 . . ? C57 C58 H58A 109.5 . . ? C57 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C57 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C55 O11 C57 110.1(19) . . ? C60 C59 C64 120.0 . . ? C60 C59 N2 117.9(16) . . ? C64 C59 N2 122.1(16) . . ? C59 C60 C61 120.0 . . ? C59 C60 H60 120.0 . . ? C61 C60 H60 120.0 . . ? C62 C61 C60 120.0 . . ? C62 C61 H61 120.0 . . ? C60 C61 H61 120.0 . . ? O13 C62 C61 117.8(15) . . ? O13 C62 C63 122.2(15) . . ? C61 C62 C63 120.0 . . ? C62 C63 C64 120.0 . . ? C62 C63 H63 120.0 . . ? C64 C63 H63 120.0 . . ? C63 C64 C59 120.0 . . ? C63 C64 H64 120.0 . . ? C59 C64 H64 120.0 . . ? O13 C65 H65A 109.5 . . ? O13 C65 H65B 109.5 . . ? H65A C65 H65B 109.5 . . ? O13 C65 H65C 109.5 . . ? H65A C65 H65C 109.5 . . ? H65B C65 H65C 109.5 . . ? C62 O13 C65 119.5(15) . . ? C67 C66 C71 120.00(5) . . ? C67 C66 N1 133(3) . . ? C71 C66 N1 107(3) . . ? C68 C67 C66 120.0 . . ? C68 C67 H67A 120.0 . . ? C66 C67 H67A 120.0 . . ? C67 C68 C69 120.0 . . ? C67 C68 H68A 120.0 . . ? C69 C68 H68A 120.0 . . ? O14 C69 C68 108(3) . . ? O14 C69 C70 132(3) . . ? C68 C69 C70 120.00(5) . . ? C71 C70 C69 120.0 . . ? C71 C70 H70A 120.0 . . ? C69 C70 H70A 120.0 . . ? C70 C71 C66 120.0 . . ? C70 C71 H71A 120.0 . . ? C66 C71 H71A 120.0 . . ? O14 C72 H72A 109.5 . . ? O14 C72 H72B 109.5 . . ? H72A C72 H72B 109.5 . . ? O14 C72 H72C 109.5 . . ? H72A C72 H72C 109.5 . . ? H72B C72 H72C 109.5 . . ? C69 O14 C72 118.6(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 C6 C1 C2 C3 -3.1(19) . . . . ? C1 C2 C3 C4 1(2) . . . . ? C1 C2 C3 Br1 -179.8(10) . . . . ? C2 C3 C4 C5 0(2) . . . . ? Br1 C3 C4 C5 -179.3(10) . . . . ? C3 C4 C5 C6 1(2) . . . . ? C4 C5 C6 C1 -3.6(19) . . . . ? C4 C5 C6 C7 178.4(13) . . . . ? C2 C1 C6 C5 4.4(18) . . . . ? C2 C1 C6 C7 -177.5(11) . . . . ? C5 C6 C7 O1 25.0(17) . . . . ? C1 C6 C7 O1 -152.8(12) . . . . ? C5 C6 C7 C8 -95.9(14) . . . . ? C1 C6 C7 C8 86.2(15) . . . . ? O1 C7 C8 C12 -176.2(10) . . . . ? C6 C7 C8 C12 -58.9(15) . . . . ? O1 C7 C8 C9 -57.6(14) . . . . ? C6 C7 C8 C9 59.8(14) . . . . ? C12 C8 C9 C10 23.7(14) . . . . ? C7 C8 C9 C10 -101.9(13) . . . . ? C8 C9 C10 C11 -32.8(16) . . . . ? C9 C10 C11 C12 28.1(16) . . . . ? C7 C8 C12 C13 -63.6(17) . . . . ? C9 C8 C12 C13 171.9(12) . . . . ? C7 C8 C12 C11 117.6(13) . . . . ? C9 C8 C12 C11 -6.9(14) . . . . ? C10 C11 C12 C13 168.6(13) . . . . ? C10 C11 C12 C8 -12.7(15) . . . . ? C8 C12 C13 N1 -4(2) . . . . ? C11 C12 C13 N1 174.7(11) . . . . ? C19 C14 C15 C16 0.0 . . . . ? N1 C14 C15 C16 180.0(3) . . . . ? C14 C15 C16 C17 0.0 . . . . ? C15 C16 C17 O2 -179.8(3) . . . . ? C15 C16 C17 C18 0.0 . . . . ? O2 C17 C18 C19 179.8(3) . . . . ? C16 C17 C18 C19 0.0 . . . . ? C17 C18 C19 C14 0.0 . . . . ? C15 C14 C19 C18 0.0 . . . . ? N1 C14 C19 C18 -180.0(3) . . . . ? O4 C20 N1 C13 -11.3(18) . . . . ? O3 C20 N1 C13 172.4(10) . . . . ? O4 C20 N1 C14 177.4(12) . . . . ? O3 C20 N1 C14 1.1(16) . . . . ? O4 C20 N1 C66 -169(3) . . . . ? O3 C20 N1 C66 15(3) . . . . ? C12 C13 N1 C20 128.6(13) . . . . ? C12 C13 N1 C14 -59.4(15) . . . . ? C12 C13 N1 C66 -72(2) . . . . ? C15 C14 N1 C20 125.6(13) . . . . ? C19 C14 N1 C20 -54.4(13) . . . . ? C15 C14 N1 C13 -45.7(10) . . . . ? C19 C14 N1 C13 134.3(10) . . . . ? C15 C14 N1 C66 38(5) . . . . ? C19 C14 N1 C66 -142(5) . . . . ? C16 C17 O2 C25 -158.5(16) . . . . ? C18 C17 O2 C25 21.7(16) . . . . ? O4 C20 O3 C21 -17.1(19) . . . . ? N1 C20 O3 C21 159.0(10) . . . . ? C22 C21 O3 C20 66.1(15) . . . . ? C23 C21 O3 C20 -58.8(15) . . . . ? C24 C21 O3 C20 -178.8(10) . . . . ? C31 C26 C27 C28 -3.9(19) . . . . ? C26 C27 C28 C29 -0.1(19) . . . . ? C26 C27 C28 Br2 -177.0(9) . . . . ? C27 C28 C29 C30 4(2) . . . . ? Br2 C28 C29 C30 -179.5(10) . . . . ? C28 C29 C30 C31 -3(2) . . . . ? C29 C30 C31 C26 -0.8(18) . . . . ? C29 C30 C31 C32 177.8(13) . . . . ? C27 C26 C31 C30 4.3(17) . . . . ? C27 C26 C31 C32 -174.3(11) . . . . ? C30 C31 C32 O5 33.2(17) . . . . ? C26 C31 C32 O5 -148.3(11) . . . . ? C30 C31 C32 C33 -91.5(14) . . . . ? C26 C31 C32 C33 87.0(14) . . . . ? O5 C32 C33 C34 -63.8(12) . . . . ? C31 C32 C33 C34 59.8(13) . . . . ? O5 C32 C33 C37 179.7(9) . . . . ? C31 C32 C33 C37 -56.8(14) . . . . ? C32 C33 C34 C35 -95.0(13) . . . . ? C37 C33 C34 C35 25.8(14) . . . . ? C33 C34 C35 C36 -33.3(16) . . . . ? C34 C35 C36 C37 27.1(17) . . . . ? C35 C36 C37 C38 169.9(15) . . . . ? C35 C36 C37 C33 -10.9(16) . . . . ? C34 C33 C37 C38 169.9(14) . . . . ? C32 C33 C37 C38 -68.4(17) . . . . ? C34 C33 C37 C36 -9.3(14) . . . . ? C32 C33 C37 C36 112.4(12) . . . . ? C36 C37 C38 N2 176.2(12) . . . . ? C33 C37 C38 N2 -3(2) . . . . ? C44 C39 C40 C41 0.0 . . . . ? N2 C39 C40 C41 179.8(3) . . . . ? C39 C40 C41 C42 0.0 . . . . ? C40 C41 C42 O6 -171.7(12) . . . . ? C40 C41 C42 C43 0.0 . . . . ? O6 C42 C43 C44 170.4(14) . . . . ? C41 C42 C43 C44 0.0 . . . . ? C42 C43 C44 C39 0.0 . . . . ? C40 C39 C44 C43 0.0 . . . . ? N2 C39 C44 C43 -179.8(3) . . . . ? O8 C45 N2 C39 -167.9(14) . . . . ? O7 C45 N2 C39 11.8(17) . . . . ? O8 C45 N2 C59 -177.7(15) . . . . ? O7 C45 N2 C59 2.1(17) . . . . ? O8 C45 N2 C38 -4.9(17) . . . . ? O7 C45 N2 C38 174.9(9) . . . . ? C40 C39 N2 C45 106.7(12) . . . . ? C44 C39 N2 C45 -73.5(12) . . . . ? C40 C39 N2 C59 -150(8) . . . . ? C44 C39 N2 C59 29(8) . . . . ? C40 C39 N2 C38 -56.6(10) . . . . ? C44 C39 N2 C38 123.2(10) . . . . ? C37 C38 N2 C45 124.0(14) . . . . ? C37 C38 N2 C39 -71.6(17) . . . . ? C37 C38 N2 C59 -62.5(17) . . . . ? C43 C42 O6 C50 8(2) . . . . ? C41 C42 O6 C50 178.7(17) . . . . ? O8 C45 O7 C46 -15.8(18) . . . . ? N2 C45 O7 C46 164.5(11) . . . . ? C47 C46 O7 C45 66.0(14) . . . . ? C49 C46 O7 C45 -173.9(10) . . . . ? C48 C46 O7 C45 -56.5(15) . . . . ? O10 C51 O9 C53 19(10) . . . . ? C52 C51 O9 C53 -155(6) . . . . ? C54 C53 O9 C51 169(5) . . . . ? O12 C55 O11 C57 -25(13) . . . . ? C56 C55 O11 C57 143(10) . . . . ? C58 C57 O11 C55 102(9) . . . . ? C45 N2 C59 C60 -55.5(13) . . . . ? C39 N2 C59 C60 -138(8) . . . . ? C38 N2 C59 C60 131.6(11) . . . . ? C45 N2 C59 C64 124.6(13) . . . . ? C39 N2 C59 C64 42(8) . . . . ? C38 N2 C59 C64 -48.3(11) . . . . ? C64 C59 C60 C61 0.0 . . . . ? N2 C59 C60 C61 -179.9(3) . . . . ? C59 C60 C61 C62 0.0 . . . . ? C60 C61 C62 O13 179.3(17) . . . . ? C60 C61 C62 C63 0.0 . . . . ? O13 C62 C63 C64 -179.3(17) . . . . ? C61 C62 C63 C64 0.0 . . . . ? C62 C63 C64 C59 0.0 . . . . ? C60 C59 C64 C63 0.0 . . . . ? N2 C59 C64 C63 179.9(3) . . . . ? C61 C62 O13 C65 -179(2) . . . . ? C63 C62 O13 C65 0(3) . . . . ? C20 N1 C66 C67 102(3) . . . . ? C13 N1 C66 C67 -56(2) . . . . ? C14 N1 C66 C67 -157(5) . . . . ? C20 N1 C66 C71 -77(3) . . . . ? C13 N1 C66 C71 124(2) . . . . ? C14 N1 C66 C71 23(5) . . . . ? C71 C66 C67 C68 0.0 . . . . ? N1 C66 C67 C68 -179.9(3) . . . . ? C66 C67 C68 C69 0.0 . . . . ? C67 C68 C69 O14 180.0(3) . . . . ? C67 C68 C69 C70 0.0 . . . . ? O14 C69 C70 C71 -180.0(3) . . . . ? C68 C69 C70 C71 0.0 . . . . ? C69 C70 C71 C66 0.0 . . . . ? C67 C66 C71 C70 0.0 . . . . ? N1 C66 C71 C70 179.9(3) . . . . ? C68 C69 O14 C72 165(5) . . . . ? C70 C69 O14 C72 -15(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1B O4 0.84 1.98 2.810(12) 172.0 1_655 O5 H5B O8 0.84 1.94 2.766(13) 166.8 1_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 21.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.800 _refine_diff_density_min -0.572 _refine_diff_density_rms 0.095 _vrf_THETM01_p26zas ; PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550 RESPONSE: The best available single crystal produced a weak diffraction pattern. The mean I/\s(I) for reflections beyond 1.05\%A resolution was less than 1. Beyond 0.95\%A resolution less than 10% of the data werre observed at the 2\s level so all calculations were limited to 0.95\%A resolution. ; _vrf_PLAT023_p26zas ; PROBLEM: Resolution (too) Low [sin(th)/Lambda < 0.6]..... 21.99 Deg. RESPONSE: The best available single crystal produced a weak diffraction pattern. The mean I/\s(I) for reflections beyond 1.05\%A resolution was less than 1. Beyond 0.95\%A resolution less than 10% of the data werre observed at the 2\s level so all calculations were limited to 0.95\%A resolution. ; _vrf_PLAT027_p26zas ; PROBLEM: _diffrn_reflns_theta_full (too) Low ............ 21.99 Deg. RESPONSE: The best available single crystal produced a weak diffraction pattern. The mean I/\s(I) for reflections beyond 1.05\%A resolution was less than 1. Beyond 0.95\%A resolution less than 10% of the data werre observed at the 2\s level so all calculations were limited to 0.95\%A resolution. ; _vrf_PLAT432_p26zas ; PROBLEM: Short Inter X...Y Contact C67 .. C72 = 2.77 Ang. RESPONSE: The proposed model describes two disordered positions for the p-methoxyphenyl groups in addition to the ethylacetate solvate. Positions for these disordered groups were idealized and poorly determined but chemically reasonable. ; # end Validation Reply Form _publ_requested_category CO _publ_section_references ; Sheldrick, G.M. (2001). SHELX-97-2. Program for crystal structure solution and refinement. Institute fur anorg chemie, G\"ottingen, Germany. Bruker AXS, Inc. (2001). Madison, Wisconsin, USA. ; _publ_section_figure_captions ; Figure 1. SHELXTL (Bruker, 2000) plot showing host molecule 1 using 35% probability ellipsoids for non-H atoms and circles of arbitrary size for H atoms; minor site disordered positions were omitted for clarity. Figure 2. SHELXTL (Bruker, 2000) plot showing host molecule 2 using 35% probability ellipsoids for non-H atoms and circles of arbitrary size for H atoms; minor site disordered positions were omitted for clarity. ; _publ_section_exptl_prep ; Crystals were grown from ethylacetate. The largest and best available single crystal produced a weak diffraction pattern. The mean I/\s(I) for reflections beyond 1.05\%A resolution was less than 1. Beyond 0.95\%A resolution less than 10% of the data werre observed at the 2\s level so all calculations were limited to 0.95\%A resolution. Five frame series were filtered for statistical outliers then corrected for absorption by integration using SHELXTL/XPREP (Bruker, 2001) before using SAINT/SADABS (Bruker, 2001) to sort, merge, and scale the combined data. A series of identical frames was collected twice during the experiment to monitor decay. No decay correction was applied. ; _publ_section_exptl_refinement ; Systematic conditions suggested the ambiguous space group. Structure was solved by direct methods (Sheldrick, 2001). The proposed model includes disordered sites for the p-methoxyphenyl moieties of the two chemically equivalent host molecules in addition to disordered sites for the ethylacetate solvate molecule. Disordered groups were restrained to ideal geometry with an effective standard deviation of 0.01\%A for bond lengths and 0.02\%A for bond angles. Methyl H atom positions, R-CH~3~, were optimized by rotation about R-C bonds with idealized C-H, R--H and H--H distances. Hydroxyl H atom positions, R-OH, were optimized by rotation about R-O bonds with idealized O-H and R--H distances. Remaining H atoms were included as riding idealized contributors. Methyl and hydroxyl H atom U's were assigned as 1.5 times Ueq of adjacent atom; remaining H atom U's were assigned as 1.2 times adjacent Ueq. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F^2^ (Sheldrick, 2001). The highest peaks in the final difference Fourier map were in the vicinity of the disordered p-methoxyphenyl group in the first molecule suggesting possible additional disorder at this site; the final map had no other significant features. Unusually anisotropic displacement parameters for the five-membered rings gave artificially short C-C bond lengths and suggested possible additional disorder for these rings. A final analysis of variance between observed and calculated structure factors showed slight dependence on amplitude. ; _publ_contact_author ; Peter Beak University of Illinois at Urbana-Champaign Department of Chemistry, Roger Adams Laboratory 600 South Mathews Avenue Urbana, Illinois 61801 USA ; _publ_contact_author_phone '1 217 333 2805' _publ_contact_author_fax '1 217 244 8068' _publ_contact_author_email beak@scs.uiuc.edu _publ_contact_letter ; Please consider this CIF submission from a publication in J. Org. Chem. ; _publ_requested_journal 'J. Org. Chem.' _publ_requested_coeditor_name ? _publ_section_title ; Asymmetric Lithiation-Substitution Sequences of Substituted Allyl Amines ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_acknowledgements ; We are grateful to the National Institutes of Health(GM-18874) for support of this work.The Materials Chemistry Laboratory at the Univeristy of Illinois was supported in part by Grant No. NSF CHE 95-03145 from the National Science Foundation. ; loop_ _publ_author_name _publ_author_address 'Beak, Peter' ; University of Illinois at Urbana-Champaign Department of Chemistry, Roger Adams Laboratory 600 South Mathews Avenue Urbana, Illinois 61801 USA ; 'Lee, Suk Joong' ; University of Illinois at Urbana-Champaign Department of Chemistry, Roger Adams Laboratory 600 South Mathews Avenue Urbana, Illinois 61801 USA ; 'Kim, Dwight D.' ; University of Illinois at Urbana-Champaign Department of Chemistry, Roger Adams Laboratory 600 South Mathews Avenue Urbana, Illinois 61801 USA ; loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 1.00 0.0300 0.00 0.00 -1.00 0.0300 0.00 1.00 1.00 0.0300 0.00 1.00 -1.00 0.0300 0.00 -1.00 0.00 0.0700 1.00 0.00 1.00 0.2400 -1.00 1.00 -1.00 0.2200