#------------------------------------------------------------------------------ #$Date: 2014-12-24 13:20:49 +0200 (Wed, 24 Dec 2014) $ #$Revision: 129046 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/61/7116104.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7116104 loop_ _publ_author_name 'Yang Li' 'Francisco Javier Lopez-Delgado' 'Danny Kaare Bech Jorgensen' 'Rune Pagh Nielsen' 'Hao Jiang' 'Karl Anker Jorgensen' _publ_section_title ; Trienamine-mediated asymmetric [4+2]-cycloaddition of alpha,beta-unsaturated ester surrogates applying 4-nitro-5-styrylisoxazoles ; _journal_name_full Chem.Commun. _journal_page_first 15689 _journal_paper_doi 10.1039/C4cc08171D _journal_volume 50 _journal_year 2014 _chemical_absolute_configuration ad _chemical_formula_moiety 'C27 H27 Br N2 O5' _chemical_formula_sum 'C27 H27 Br N2 O5' _chemical_formula_weight 539.41 _chemical_name_systematic '2-(5-hydroxy-4-methyl-2-(4-methyl-3-nitropyrrolidin-2-yl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-3-yl)ethyl 2-methylbenzoate' _chemical_properties_physical Air-sensitive _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2014-08-21 _audit_creation_method ; Olex2 1.2 (compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862) ; _cell_angle_alpha 90 _cell_angle_beta 102.9605(13) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.89050(7) _cell_length_b 23.7962(3) _cell_length_c 9.09712(12) _cell_measurement_reflns_used 23509 _cell_measurement_temperature 99.99(10) _cell_measurement_theta_max 32.7650 _cell_measurement_theta_min 2.8720 _cell_volume 1242.67(3) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 99.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.3590 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.961 _diffrn_measurement_details ; 1 omega -70.00 107.00 1.0000 22.5000 omega____ theta____ kappa____ phi______ frames - 18.5695 0.0000 -120.0000 177 2 omega -14.00 95.00 1.0000 22.5000 omega____ theta____ kappa____ phi______ frames - 18.5695 77.0000 30.0000 109 3 omega -14.00 95.00 1.0000 22.5000 omega____ theta____ kappa____ phi______ frames - 18.5695 77.0000 -90.0000 109 4 omega -56.00 43.00 1.0000 22.5000 omega____ theta____ kappa____ phi______ frames - 18.5695 -38.0000 30.0000 99 5 omega -80.00 -7.00 1.0000 22.5000 omega____ theta____ kappa____ phi______ frames - -19.8195 133.0000 74.0000 73 6 omega 34.00 106.00 1.0000 22.5000 omega____ theta____ kappa____ phi______ frames - 18.5695 -178.0000 90.0000 72 7 omega 7.00 79.00 1.0000 22.5000 omega____ theta____ kappa____ phi______ frames - 18.5695 -133.0000 6.0000 72 8 omega -10.00 92.00 1.0000 22.5000 omega____ theta____ kappa____ phi______ frames - 18.5695 57.0000 -180.0000 102 9 omega -44.00 54.00 1.0000 22.5000 omega____ theta____ kappa____ phi______ frames - -19.8195 38.0000 -180.0000 98 10 omega -107.00 -34.00 1.0000 22.5000 omega____ theta____ kappa____ phi______ frames - -19.8195 178.0000 150.0000 73 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Single source at offset, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0047798000 _diffrn_orient_matrix_UB_12 0.0226077000 _diffrn_orient_matrix_UB_13 0.0514085000 _diffrn_orient_matrix_UB_21 -0.0084711000 _diffrn_orient_matrix_UB_22 0.0194239000 _diffrn_orient_matrix_UB_23 -0.0601266000 _diffrn_orient_matrix_UB_31 -0.1231925000 _diffrn_orient_matrix_UB_32 -0.0004571000 _diffrn_orient_matrix_UB_33 -0.0118647000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_unetI/netI 0.0234 _diffrn_reflns_laue_measured_fraction_full 1.000 _diffrn_reflns_laue_measured_fraction_max 0.961 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 40829 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.942 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 32.960 _diffrn_reflns_theta_min 2.297 _diffrn_source 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 1.695 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'Clear yellowish' _exptl_crystal_density_diffrn 1.442 _exptl_crystal_F_000 556 _exptl_crystal_size_max 0.3046 _exptl_crystal_size_mid 0.1741 _exptl_crystal_size_min 0.1026 _refine_diff_density_max 3.236 _refine_diff_density_min -0.795 _refine_diff_density_rms 0.119 _refine_ls_abs_structure_details ; Flack x determined using 3849 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.001(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 318 _refine_ls_number_reflns 8771 _refine_ls_number_restraints 268 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0491 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+1.8490P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1333 _refine_ls_wR_factor_ref 0.1355 _reflns_Friedel_coverage 0.922 _reflns_friedel_fraction_full 1.000 _reflns_friedel_fraction_max 0.923 _reflns_number_gt 8404 _reflns_number_total 8771 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file c4cc08171d2.cif _[local]_cod_data_source_block exp_2279 _cod_database_code 7116104 _shelxl_version_number 2014/6 _chemical_oxdiff_formula 'C27 H27 N2 O5 Br' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _reflns_odcompleteness_completeness 99.92 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2. Uiso/Uaniso restraints and constraints Uiso(O1H) = Uiso(O1I) 3. Rigid body (RIGU) restrains All non-hydrogen atoms with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 4. Others Sof(O1I)=1-FVAR(1) Sof(O1H)=FVAR(1) 5.a Ternary CH refined with riding coordinates: C4(H4), C11(H11), C12(H12) 5.b Secondary CH2 refined with riding coordinates: C6(H6A,H6B), C9(H9A,H9B), C19(H19A,H19B) 5.c Aromatic/amide H refined with riding coordinates: C5(H5), C15(H15), C17(H17), N22(H22), C1E(H1E), C1G(H1G), C1K(H1K), C1M(H1M), C1Y(H1Y), C2(H2), C1(H1) 5.d Idealised Me refined as rotating group: C1C(H1CA,H1CB,H1CC), C1D(H1DA,H1DB,H1DC) 5.e Idealised tetrahedral OH refined as rotating group: O1P(H1P) ; _shelx_res_file ; TITL exp_2279 in P21 #4 CELL 0.71073 5.890503 23.796166 9.097116 90 102.9605 90 ZERR 2 0.000074 0.000318 0.000121 0 0.0013 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O Br UNIT 54 54 4 10 2 RIGU EADP O1H O1I L.S. 4 0 0 PLAN 20 REM reset to P21 #4 BOND fmap 2 53 acta REM C:/Crystals/2014_07_24b/exp_2279/exp_2279.hkl WGHT 0.080000 1.849000 FVAR 4.96993 0.44252 BR1 5 0.725393 0.406690 -0.045933 11.00000 0.01644 0.02873 = 0.02488 0.00210 0.00546 0.00442 O1 4 0.834171 0.269215 0.046770 11.00000 0.01712 0.02265 = 0.01593 -0.00127 0.00521 -0.00773 O2 4 0.326315 0.383746 0.104921 11.00000 0.01548 0.01620 = 0.01308 -0.00009 0.00223 0.00154 C3 1 0.301902 0.438342 0.132082 11.00000 0.01751 0.01093 = 0.01783 0.00025 0.00100 -0.00258 C5 1 0.232459 0.176940 0.166653 11.00000 0.01018 0.01105 = 0.00926 -0.00225 0.00100 -0.00544 AFIX 43 H5 2 0.096187 0.157518 0.168674 11.00000 -1.20000 AFIX 0 C4 1 0.730614 0.263189 0.355305 11.00000 0.01053 0.01041 = 0.00914 -0.00018 0.00244 -0.00196 AFIX 13 H4 2 0.881194 0.259560 0.327310 11.00000 -1.20000 AFIX 0 C7 1 0.333271 0.181539 0.052201 11.00000 0.01416 0.01235 = 0.01209 -0.00119 0.00112 -0.00294 C8 1 0.556750 0.230578 0.242938 11.00000 0.01163 0.00786 = 0.00994 0.00023 0.00303 -0.00068 C6 1 0.967801 0.270173 0.617674 11.00000 0.01592 0.01688 = 0.01027 -0.00124 0.00061 -0.00354 AFIX 23 H6A 2 0.963149 0.263619 0.722197 11.00000 -1.20000 H6B 2 1.110803 0.253677 0.601499 11.00000 -1.20000 AFIX 0 C9 1 0.414260 0.339615 0.359486 11.00000 0.01460 0.01307 = 0.01483 -0.00068 0.00623 0.00104 AFIX 23 H9A 2 0.359840 0.310068 0.416516 11.00000 -1.20000 H9B 2 0.410972 0.374572 0.413813 11.00000 -1.20000 AFIX 0 C10 1 0.798486 0.176195 0.528483 11.00000 0.01310 0.01259 = 0.01002 0.00147 0.00260 -0.00045 C11 1 0.670312 0.326788 0.352406 11.00000 0.01253 0.00869 = 0.01224 -0.00072 0.00402 -0.00189 AFIX 13 H11 2 0.691552 0.341461 0.255729 11.00000 -1.20000 AFIX 0 C12 1 0.760073 0.239264 0.516378 11.00000 0.01150 0.01172 = 0.00906 0.00021 0.00242 -0.00033 AFIX 13 H12 2 0.619441 0.248194 0.552385 11.00000 -1.20000 AFIX 0 C14 1 0.536758 0.215904 0.094841 11.00000 0.01338 0.01075 = 0.00922 -0.00131 0.00329 -0.00236 C13 1 0.976700 0.332501 0.592819 11.00000 0.01718 0.01540 = 0.01293 -0.00466 0.00286 -0.00549 C15 1 0.655209 0.142305 0.593872 11.00000 0.01642 0.01353 = 0.01131 0.00149 0.00414 -0.00215 AFIX 43 H15 2 0.525455 0.157879 0.620718 11.00000 -1.20000 AFIX 0 C17 1 0.987882 0.151567 0.483499 11.00000 0.01678 0.01588 = 0.01563 0.00280 0.00651 0.00165 AFIX 43 H17 2 1.082196 0.173360 0.436702 11.00000 -1.20000 AFIX 0 C18 1 0.840168 0.358513 0.475411 11.00000 0.01607 0.01107 = 0.01506 -0.00351 0.00566 -0.00507 C19 1 0.247280 0.344370 0.206769 11.00000 0.01398 0.01021 = 0.01898 -0.00035 0.00314 -0.00150 AFIX 23 H19A 2 0.227438 0.307535 0.159966 11.00000 -1.20000 H19B 2 0.096562 0.356532 0.221103 11.00000 -1.20000 AFIX 0 O1A 4 0.232271 0.455956 0.238758 11.00000 0.03882 0.01313 = 0.02576 -0.00083 0.01453 0.00274 N22 3 0.374827 0.207831 0.287108 11.00000 0.00773 0.00986 = 0.00577 -0.00155 0.00283 -0.00549 AFIX 43 H22 2 0.347766 0.211372 0.375696 11.00000 -1.20000 AFIX 0 C1B 1 0.521971 0.469309 -0.071090 11.00000 0.01494 0.01980 = 0.01748 0.00029 0.00154 -0.00173 C1C 1 0.841012 0.421138 0.449946 11.00000 0.02736 0.00926 = 0.02698 -0.00220 0.00746 -0.00521 AFIX 137 H1CA 2 0.903669 0.428987 0.363382 11.00000 -1.50000 H1CB 2 0.935319 0.439062 0.537103 11.00000 -1.50000 H1CC 2 0.684584 0.435225 0.433143 11.00000 -1.50000 AFIX 0 C1D 1 0.233092 0.151980 -0.092793 11.00000 0.02234 0.02129 = 0.01448 -0.00429 -0.00030 -0.00823 AFIX 137 H1DA 2 0.326545 0.119680 -0.102021 11.00000 -1.50000 H1DB 2 0.231537 0.177044 -0.175705 11.00000 -1.50000 H1DC 2 0.076845 0.140231 -0.093790 11.00000 -1.50000 AFIX 0 C1E 1 0.703996 0.085223 0.619621 11.00000 0.02107 0.01335 = 0.01741 0.00269 0.00596 -0.00161 AFIX 43 H1E 2 0.608369 0.063297 0.665066 11.00000 -1.20000 AFIX 0 C1F 1 0.353468 0.476986 0.013893 11.00000 0.01750 0.01423 = 0.01597 -0.00116 0.00111 -0.00292 C1G 1 0.210030 0.527942 -0.014393 11.00000 0.02308 0.04556 = 0.01538 -0.00894 0.00714 -0.01675 AFIX 43 H1G 2 0.099053 0.534885 0.041720 11.00000 -1.20000 AFIX 0 PART 1 O1H 4 0.628513 0.220342 -0.136881 21.00000 0.02168 PART 0 N1I 3 0.686919 0.233165 0.000166 11.00000 0.02368 0.02303 = 0.01395 -0.00466 0.00765 -0.00942 C1K 1 0.238840 0.564966 -0.122193 11.00000 0.02968 0.01844 = 0.02391 0.00523 0.00153 0.00294 AFIX 43 H1K 2 0.143745 0.596539 -0.141429 11.00000 -1.20000 AFIX 0 C1M 1 1.036033 0.094310 0.508589 11.00000 0.01929 0.01851 = 0.02232 0.00082 0.00724 0.00658 AFIX 43 H1M 2 1.162884 0.078332 0.479086 11.00000 -1.20000 AFIX 0 O1P 4 1.161847 0.361079 0.711330 11.00000 0.04472 0.04433 = 0.03477 -0.00920 -0.00321 -0.01281 AFIX 147 H1P 2 1.290352 0.348750 0.707417 11.00000 -1.50000 AFIX 0 C1Y 1 0.894633 0.061071 0.577667 11.00000 0.02714 0.01207 = 0.02233 0.00305 0.00684 0.00437 AFIX 43 H1Y 2 0.927752 0.023136 0.595415 11.00000 -1.20000 AFIX 0 C2 1 0.409448 0.556327 -0.204763 11.00000 0.03062 0.02434 = 0.01787 0.00429 0.00175 -0.00654 AFIX 43 H2 2 0.427811 0.582338 -0.277510 11.00000 -1.20000 AFIX 0 C1 1 0.550339 0.509593 -0.179087 11.00000 0.02280 0.02977 = 0.01678 0.00117 0.00544 -0.00727 AFIX 43 H1 2 0.665083 0.504557 -0.233380 11.00000 -1.20000 AFIX 0 PART 2 O1I 4 0.686973 0.203481 -0.112373 -21.00000 0.02168 HKLF 4 REM exp_2279 in P21 #4 REM R1 = 0.0491 for 8404 Fo > 4sig(Fo) and 0.0518 for all 8771 data REM 318 parameters refined using 268 restraints END WGHT 0.0794 1.8592 REM Highest difference peak 3.236, deepest hole -0.795, 1-sigma level 0.119 Q1 1 0.1631 0.5586 -0.0329 11.00000 0.05 3.24 Q2 1 0.1581 0.2599 -0.0340 11.00000 0.05 1.70 Q3 1 0.5654 0.2380 -0.1528 11.00000 0.05 0.90 Q4 1 0.2972 0.2603 -0.0547 11.00000 0.05 0.69 Q5 1 0.3881 0.2601 0.1228 11.00000 0.05 0.66 Q6 1 1.1132 0.3585 0.8170 11.00000 0.05 0.66 Q7 1 0.4461 0.4606 -0.0176 11.00000 0.05 0.63 Q8 1 0.5962 0.4162 -0.0588 11.00000 0.05 0.63 Q9 1 1.1816 0.4062 0.6789 11.00000 0.05 0.51 Q10 1 0.2817 0.1230 0.0455 11.00000 0.05 0.51 Q11 1 0.7284 0.1831 -0.0874 11.00000 0.05 0.49 Q12 1 0.5520 0.5760 -0.1539 11.00000 0.05 0.48 Q13 1 0.6330 0.1063 0.7054 11.00000 0.05 0.46 Q14 1 0.2968 0.4568 0.1974 11.00000 0.05 0.46 Q15 1 0.5946 0.2243 0.0473 11.00000 0.05 0.45 Q16 1 0.5641 0.1054 0.7264 11.00000 0.05 0.45 Q17 1 0.8811 0.1637 0.4999 11.00000 0.05 0.43 Q18 1 0.8708 0.4062 -0.0377 11.00000 0.05 0.43 Q19 1 0.7394 0.1395 -0.1564 11.00000 0.05 0.43 Q20 1 0.7293 0.4371 -0.1643 11.00000 0.05 0.42 ; _shelx_res_checksum 25045 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.72539(6) 0.40669(2) -0.04593(4) 0.02322(11) Uani 1 1 d . . . . O1 O 0.8342(5) 0.26922(13) 0.0468(3) 0.0183(5) Uani 1 1 d . . . . O2 O 0.3263(5) 0.38375(12) 0.1049(3) 0.0151(5) Uani 1 1 d . . . . C3 C 0.3019(7) 0.43834(15) 0.1321(5) 0.0159(6) Uani 1 1 d . . . . C5 C 0.2325(6) 0.17694(14) 0.1667(3) 0.0103(5) Uani 1 1 d . . . . H5 H 0.0962 0.1575 0.1687 0.012 Uiso 1 1 calc R . . . C4 C 0.7306(6) 0.26319(13) 0.3553(4) 0.0100(5) Uani 1 1 d . . . . H4 H 0.8812 0.2596 0.3273 0.012 Uiso 1 1 calc R . . . C7 C 0.3333(6) 0.18154(15) 0.0522(4) 0.0132(5) Uani 1 1 d . . . . C8 C 0.5567(6) 0.23058(13) 0.2429(4) 0.0097(5) Uani 1 1 d . . . . C6 C 0.9678(6) 0.27017(15) 0.6177(4) 0.0147(6) Uani 1 1 d . . . . H6A H 0.9631 0.2636 0.7222 0.018 Uiso 1 1 calc R . . . H6B H 1.1108 0.2537 0.6015 0.018 Uiso 1 1 calc R . . . C9 C 0.4143(6) 0.33962(15) 0.3595(4) 0.0137(6) Uani 1 1 d . . . . H9A H 0.3598 0.3101 0.4165 0.016 Uiso 1 1 calc R . . . H9B H 0.4110 0.3746 0.4138 0.016 Uiso 1 1 calc R . . . C10 C 0.7985(6) 0.17619(15) 0.5285(4) 0.0119(5) Uani 1 1 d . . . . C11 C 0.6703(6) 0.32679(13) 0.3524(4) 0.0110(5) Uani 1 1 d . . . . H11 H 0.6916 0.3415 0.2557 0.013 Uiso 1 1 calc R . . . C12 C 0.7601(6) 0.23926(14) 0.5164(4) 0.0107(5) Uani 1 1 d . . . . H12 H 0.6194 0.2482 0.5524 0.013 Uiso 1 1 calc R . . . C14 C 0.5368(6) 0.21590(13) 0.0948(4) 0.0110(5) Uani 1 1 d . . . . C13 C 0.9767(7) 0.33250(15) 0.5928(4) 0.0153(6) Uani 1 1 d . . . . C15 C 0.6552(6) 0.14231(15) 0.5939(4) 0.0136(6) Uani 1 1 d . . . . H15 H 0.5255 0.1579 0.6207 0.016 Uiso 1 1 calc R . . . C17 C 0.9879(7) 0.15157(16) 0.4835(4) 0.0156(6) Uani 1 1 d . . . . H17 H 1.0822 0.1734 0.4367 0.019 Uiso 1 1 calc R . . . C18 C 0.8402(6) 0.35851(15) 0.4754(4) 0.0137(6) Uani 1 1 d . . . . C19 C 0.2473(7) 0.34437(15) 0.2068(4) 0.0145(6) Uani 1 1 d . . . . H19A H 0.2274 0.3075 0.1600 0.017 Uiso 1 1 calc R . . . H19B H 0.0966 0.3565 0.2211 0.017 Uiso 1 1 calc R . . . O1A O 0.2323(7) 0.45596(13) 0.2388(4) 0.0248(7) Uani 1 1 d . . . . N22 N 0.3748(5) 0.20783(11) 0.2871(3) 0.0076(4) Uani 1 1 d . . . . H22 H 0.3478 0.2114 0.3757 0.009 Uiso 1 1 calc R . . . C1B C 0.5220(7) 0.46931(17) -0.0711(4) 0.0177(6) Uani 1 1 d . . . . C1C C 0.8410(8) 0.42114(15) 0.4499(5) 0.0210(7) Uani 1 1 d . . . . H1CA H 0.9037 0.4290 0.3634 0.031 Uiso 1 1 calc GR . . . H1CB H 0.9353 0.4391 0.5371 0.031 Uiso 1 1 calc GR . . . H1CC H 0.6846 0.4352 0.4331 0.031 Uiso 1 1 calc GR . . . C1D C 0.2331(7) 0.15198(17) -0.0928(4) 0.0201(7) Uani 1 1 d . . . . H1DA H 0.3265 0.1197 -0.1020 0.030 Uiso 1 1 calc GR . . . H1DB H 0.2315 0.1770 -0.1757 0.030 Uiso 1 1 calc GR . . . H1DC H 0.0768 0.1402 -0.0938 0.030 Uiso 1 1 calc GR . . . C1E C 0.7040(7) 0.08522(15) 0.6196(4) 0.0170(6) Uani 1 1 d . . . . H1E H 0.6084 0.0633 0.6651 0.020 Uiso 1 1 calc R . . . C1F C 0.3535(7) 0.47699(15) 0.0139(4) 0.0163(6) Uani 1 1 d . . . . C1G C 0.2100(8) 0.5279(2) -0.0144(5) 0.0276(9) Uani 1 1 d . . . . H1G H 0.0991 0.5349 0.0417 0.033 Uiso 1 1 calc R . . . O1H O 0.6285(15) 0.2203(4) -0.1369(9) 0.0217(8) Uiso 0.443(10) 1 d . P A 1 N1I N 0.6869(6) 0.23317(16) 0.0002(4) 0.0197(6) Uani 1 1 d . . . . C1K C 0.2388(8) 0.56497(18) -0.1222(5) 0.0247(8) Uani 1 1 d . . . . H1K H 0.1437 0.5965 -0.1414 0.030 Uiso 1 1 calc R . . . C1M C 1.0360(7) 0.09431(17) 0.5086(5) 0.0196(7) Uani 1 1 d . . . . H1M H 1.1629 0.0783 0.4791 0.024 Uiso 1 1 calc R . . . O1P O 1.1618(9) 0.3611(2) 0.7113(5) 0.0432(10) Uani 1 1 d . . . . H1P H 1.2904 0.3488 0.7074 0.065 Uiso 1 1 calc GR . . . C1Y C 0.8946(8) 0.06107(16) 0.5777(5) 0.0203(7) Uani 1 1 d . . . . H1Y H 0.9278 0.0231 0.5954 0.024 Uiso 1 1 calc R . . . C2 C 0.4094(9) 0.55633(19) -0.2048(5) 0.0249(8) Uani 1 1 d . . . . H2 H 0.4278 0.5823 -0.2775 0.030 Uiso 1 1 calc R . . . C1 C 0.5503(8) 0.5096(2) -0.1791(5) 0.0230(8) Uani 1 1 d . . . . H1 H 0.6651 0.5046 -0.2334 0.028 Uiso 1 1 calc R . . . O1I O 0.6870(12) 0.2035(3) -0.1124(7) 0.0217(8) Uiso 0.557(10) 1 d . P 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 0.01644(16) 0.02873(19) 0.02488(18) 0.00210(16) 0.00546(12) 0.00442(16) O1 0.0171(12) 0.0227(13) 0.0159(12) -0.0013(9) 0.0052(9) -0.0077(10) O2 0.0155(12) 0.0162(11) 0.0131(11) -0.0001(9) 0.0022(9) 0.0015(9) C3 0.0175(16) 0.0109(13) 0.0178(15) 0.0003(11) 0.0010(12) -0.0026(11) C5 0.0102(12) 0.0110(12) 0.0093(11) -0.0023(10) 0.0010(10) -0.0054(10) C4 0.0105(12) 0.0104(12) 0.0091(12) -0.0002(9) 0.0024(9) -0.0020(9) C7 0.0142(14) 0.0123(13) 0.0121(13) -0.0012(10) 0.0011(10) -0.0029(11) C8 0.0116(13) 0.0079(11) 0.0099(12) 0.0002(9) 0.0030(10) -0.0007(9) C6 0.0159(14) 0.0169(15) 0.0103(13) -0.0012(10) 0.0006(11) -0.0035(11) C9 0.0146(14) 0.0131(13) 0.0148(14) -0.0007(11) 0.0062(11) 0.0010(11) C10 0.0131(13) 0.0126(13) 0.0100(12) 0.0015(10) 0.0026(10) -0.0004(10) C11 0.0125(13) 0.0087(12) 0.0122(13) -0.0007(9) 0.0040(10) -0.0019(10) C12 0.0115(13) 0.0117(13) 0.0091(12) 0.0002(9) 0.0024(10) -0.0003(10) C14 0.0134(13) 0.0107(13) 0.0092(12) -0.0013(9) 0.0033(10) -0.0024(10) C13 0.0172(15) 0.0154(14) 0.0129(14) -0.0047(11) 0.0029(11) -0.0055(11) C15 0.0164(15) 0.0135(13) 0.0113(13) 0.0015(10) 0.0041(11) -0.0021(11) C17 0.0168(15) 0.0159(15) 0.0156(16) 0.0028(11) 0.0065(13) 0.0017(12) C18 0.0161(14) 0.0111(13) 0.0151(14) -0.0035(10) 0.0057(11) -0.0051(10) C19 0.0140(15) 0.0102(13) 0.0190(15) -0.0003(11) 0.0031(12) -0.0015(11) O1A 0.0388(18) 0.0131(12) 0.0258(15) -0.0008(11) 0.0145(13) 0.0027(12) N22 0.0077(10) 0.0099(10) 0.0058(9) -0.0016(8) 0.0028(8) -0.0055(8) C1B 0.0149(15) 0.0198(15) 0.0175(15) 0.0003(12) 0.0015(12) -0.0017(12) C1C 0.0274(19) 0.0093(14) 0.0270(18) -0.0022(11) 0.0075(15) -0.0052(12) C1D 0.0223(18) 0.0213(17) 0.0145(15) -0.0043(12) -0.0003(12) -0.0082(13) C1E 0.0211(16) 0.0134(14) 0.0174(15) 0.0027(11) 0.0060(12) -0.0016(12) C1F 0.0175(15) 0.0142(14) 0.0160(15) -0.0012(11) 0.0011(12) -0.0029(11) C1G 0.0231(19) 0.046(3) 0.0154(16) -0.0089(16) 0.0071(14) -0.0168(17) N1I 0.0237(16) 0.0230(15) 0.0139(13) -0.0047(11) 0.0076(11) -0.0094(12) C1K 0.030(2) 0.0184(17) 0.0239(18) 0.0052(14) 0.0015(15) 0.0029(14) C1M 0.0193(17) 0.0185(16) 0.0223(17) 0.0008(13) 0.0072(13) 0.0066(13) O1P 0.045(2) 0.044(2) 0.035(2) -0.0092(17) -0.0032(18) -0.0128(19) C1Y 0.0271(18) 0.0121(14) 0.0223(17) 0.0031(12) 0.0068(14) 0.0044(13) C2 0.031(2) 0.0243(18) 0.0179(16) 0.0043(13) 0.0018(14) -0.0065(15) C1 0.0228(18) 0.030(2) 0.0168(16) 0.0012(13) 0.0054(13) -0.0073(15) 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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 3 5 0.0264 0.0001 2.9806 4.9483 0.3218 -0.2396 -0.0601 5 2 -1 0.1367 4.9500 1.9941 -0.9901 0.0178 0.0563 -0.5990 0 -1 0 0.0951 -0.0000 -0.9899 0.0006 -0.0224 -0.0193 0.0004 0 1 0 0.0623 0.0004 0.9998 -0.0001 0.0226 0.0194 -0.0005 0 1 -5 0.0496 -0.0000 0.9748 -4.9505 -0.2325 0.3166 0.0583 -5 1 1 0.1414 -4.9498 0.9733 0.9883 0.0492 0.0014 0.5976 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C3 O2 C19 116.2(3) O2 C3 C1F 114.6(3) O1A C3 O2 123.7(4) O1A C3 C1F 121.5(3) C7 C5 N22 105.9(3) C8 C4 C11 112.1(3) C8 C4 C12 111.8(3) C12 C4 C11 110.6(3) C5 C7 C14 109.4(3) C5 C7 C1D 120.1(3) C14 C7 C1D 130.5(3) C14 C8 C4 134.4(3) N22 C8 C4 118.5(3) N22 C8 C14 107.1(3) C13 C6 C12 115.5(3) C19 C9 C11 114.4(3) C15 C10 C12 120.6(3) C15 C10 C17 118.8(3) C17 C10 C12 120.5(3) C4 C11 C9 114.3(3) C18 C11 C4 111.1(3) C18 C11 C9 110.8(3) C6 C12 C4 107.2(3) C10 C12 C4 114.6(3) C10 C12 C6 110.0(3) C8 C14 C7 107.1(3) C8 C14 N1I 126.3(3) N1I C14 C7 126.6(3) C6 C13 O1P 112.4(3) C18 C13 C6 122.8(3) C18 C13 O1P 124.8(4) C10 C15 C1E 120.8(3) C10 C17 C1M 120.4(4) C13 C18 C11 122.4(3) C13 C18 C1C 123.9(3) C1C C18 C11 113.6(3) O2 C19 C9 113.2(3) C8 N22 C5 110.5(3) C1F C1B Br1 122.9(3) C1F C1B C1 120.4(4) C1 C1B Br1 116.7(3) C1Y C1E C15 120.3(3) C1B C1F C3 126.8(3) C1B C1F C1G 117.6(3) C1G C1F C3 115.6(3) C1K C1G C1F 120.2(4) O1 N1I C14 118.6(3) O1 N1I O1H 121.9(5) O1 N1I O1I 123.5(4) O1H N1I C14 117.5(4) O1I N1I C14 116.6(4) C1G C1K C2 120.9(4) C1Y C1M C17 120.3(4) C1E C1Y C1M 119.3(3) C1 C2 C1K 120.4(4) C2 C1 C1B 120.5(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C1B 1.894(4) O1 N1I 1.226(4) O2 C3 1.336(4) O2 C19 1.465(5) C3 O1A 1.210(5) C3 C1F 1.497(5) C5 C7 1.314(5) C5 N22 1.426(4) C4 C8 1.492(4) C4 C11 1.553(5) C4 C12 1.545(5) C7 C14 1.431(5) C7 C1D 1.495(5) C8 C14 1.371(4) C8 N22 1.340(4) C6 C12 1.543(5) C6 C13 1.503(5) C9 C11 1.554(5) C9 C19 1.516(5) C10 C12 1.518(5) C10 C15 1.393(5) C10 C17 1.400(5) C11 C18 1.523(5) C14 N1I 1.426(5) C13 C18 1.336(5) C13 O1P 1.512(5) C15 C1E 1.397(5) C17 C1M 1.400(6) C18 C1C 1.508(5) C1B C1F 1.400(6) C1B C1 1.409(6) C1E C1Y 1.389(6) C1F C1G 1.467(7) C1G C1K 1.357(6) O1H N1I 1.254(8) N1I O1I 1.244(7) C1K C2 1.398(7) C1M C1Y 1.396(6) C2 C1 1.376(7)