#------------------------------------------------------------------------------ #$Date: 2020-04-17 04:47:05 +0300 (Fri, 17 Apr 2020) $ #$Revision: 250878 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157472.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_7157472 loop_ _publ_author_name 'Gunnlaugsson, Thorfinnur' 'Scanlan, Eoin M.' 'Elena Calatrava-P\'erez, Elena' 'Achermann, Stefan' 'Stricker, Lucas' 'McManus, Gavin' 'Delente, Jason' 'Lynes, Amy Danielle' 'Henwood, Adam' 'Lovitt, June' 'Hawes, Chris Samuel' 'Byrne, Kevin' 'Schmitt, Wolfgang' 'Kotova, Oxana' _publ_section_title ; Fluorescent supramolecular hierarchical self-assemblies from glycosylated 4-amino- and 4-bromo-1,8-naphthalimides ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00033G _journal_year 2020 _chemical_formula_moiety '2(C16 H14 Br N O2)' _chemical_formula_sum 'C32 H28 Br2 N2 O4' _chemical_formula_weight 664.38 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2019-11-28 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-11-28 deposited with the CCDC. 2020-04-15 downloaded from the CCDC. ; _cell_angle_alpha 99.692(2) _cell_angle_beta 94.484(2) _cell_angle_gamma 92.775(2) _cell_formula_units_Z 2 _cell_length_a 4.4247(3) _cell_length_b 16.1174(10) _cell_length_c 19.4957(13) _cell_measurement_reflns_used 9604 _cell_measurement_temperature 100 _cell_measurement_theta_max 68.17 _cell_measurement_theta_min 2.79 _cell_volume 1363.61(16) _computing_cell_refinement 'SAINT V8.38A (?, 2016)' _computing_data_reduction 'SAINT V8.38A (?, 2016)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 100.01 _diffrn_detector 'Bruker APEX2 area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_unetI/netI 0.0346 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 12740 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.213 _diffrn_reflns_theta_min 2.787 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_type 'Incoatec I\ms' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 4.115 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_correction_T_min 0.5856 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0681 before and 0.0440 after correction. The Ratio of minimum to maximum transmission is 0.7776. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.959 _refine_diff_density_min -0.809 _refine_diff_density_rms 0.082 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 376 _refine_ls_number_reflns 4955 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.167 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0410 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+2.6902P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1059 _refine_ls_wR_factor_ref 0.1066 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4759 _reflns_number_total 4955 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00033g2.cif _cod_data_source_block 7 _cod_database_code 7157472 _shelx_shelxl_version_number 2016/4 _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. ; _shelx_estimated_absorpt_t_max 0.922 _shelx_estimated_absorpt_t_min 0.525 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C27-Br2 1.9 with sigma of 0.01 C25-Br3 1.9 with sigma of 0.01 3. Others Fixed Sof: Br2(0.93172) Br3(0.07071) H25(0.93) H27(0.06828) 4.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B) 4.b Aromatic/amide H refined with riding coordinates: C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C23(H23), C24(H24), C27(H27), C28(H28), C29(H29) 4.c Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C17(H17A,H17B,H17C) ; _shelx_res_file ; TITL cu_jil050_0m_a.res in P-1 cu_jil050_0m.res created by SHELXL-2016/4 at 12:09:02 on 28-Nov-2019 REM Old TITL cu_JIL050_0m in P-1 REM SHELXT solution in P-1 REM R1 0.135, Rweak 0.007, Alpha 0.052, Orientation as input REM Formula found by SHELXT: C22 N2 O4 Br2 CELL 1.54178 4.4247 16.1174 19.4957 99.692 94.484 92.775 ZERR 2 0.0003 0.001 0.0013 0.002 0.002 0.002 LATT 1 SFAC C H Br N O UNIT 64 56 4 4 8 DFIX 1.9 0.01 C27 Br2 DFIX 1.9 0.01 C25 Br3 L.S. 20 PLAN 20 SIZE 0.18 0.06 0.02 TEMP -173.14 BOND $H list 4 fmap 2 acta OMIT 0 -2 3 REM REM REM WGHT 0.042600 2.690200 FVAR 0.53439 PART 2 BR1 3 0.113694 0.399821 0.485557 11.00000 0.04984 0.01823 = 0.02635 -0.00156 0.00507 0.00528 PART 0 O1 5 -0.110287 -0.079495 0.368180 11.00000 0.03424 0.01893 = 0.03062 0.00400 -0.00079 -0.00459 N1 4 0.209659 -0.007639 0.309564 11.00000 0.02629 0.01502 = 0.02300 0.00019 -0.00012 0.00208 C1 1 0.043428 -0.189556 0.071840 11.00000 0.05371 0.04686 = 0.03377 -0.01700 0.00338 0.00114 AFIX 137 H1A 2 -0.177260 -0.186041 0.071121 11.00000 -1.50000 H1B 2 0.089544 -0.244409 0.046014 11.00000 -1.50000 H1C 2 0.130040 -0.144466 0.049940 11.00000 -1.50000 AFIX 0 O2 5 0.538446 0.065047 0.254376 11.00000 0.02970 0.02709 = 0.02716 -0.00173 0.00874 0.00000 C2 1 0.180013 -0.179856 0.147068 11.00000 0.03740 0.02335 = 0.03559 -0.00752 0.00363 0.00013 AFIX 23 H2A 2 0.401931 -0.185427 0.147360 11.00000 -1.20000 H2B 2 0.093140 -0.225894 0.168737 11.00000 -1.20000 AFIX 0 C3 1 0.121024 -0.095252 0.190633 11.00000 0.02893 0.02418 = 0.02712 -0.00350 0.00073 0.00353 AFIX 23 H3A 2 0.199467 -0.048888 0.168143 11.00000 -1.20000 H3B 2 -0.100442 -0.090657 0.192833 11.00000 -1.20000 AFIX 0 C4 1 0.275101 -0.086693 0.264318 11.00000 0.03130 0.01782 = 0.02923 -0.00185 0.00146 0.00632 AFIX 23 H4A 2 0.205561 -0.135219 0.285403 11.00000 -1.20000 H4B 2 0.497405 -0.088450 0.261887 11.00000 -1.20000 AFIX 0 C5 1 0.355476 0.066906 0.297917 11.00000 0.02311 0.02186 = 0.02065 0.00090 -0.00173 0.00336 C6 1 0.280945 0.146678 0.341361 11.00000 0.02342 0.01747 = 0.02068 0.00115 0.00014 0.00111 C7 1 0.406693 0.222243 0.330003 11.00000 0.02653 0.02398 = 0.02306 0.00356 0.00348 0.00025 AFIX 43 H7 2 0.533228 0.223209 0.292923 11.00000 -1.20000 AFIX 0 C8 1 0.349733 0.298112 0.372765 11.00000 0.03146 0.01546 = 0.02745 0.00506 0.00051 -0.00031 AFIX 43 H8 2 0.434037 0.350385 0.364277 11.00000 -1.20000 AFIX 0 C9 1 0.171266 0.295881 0.426841 11.00000 0.03076 0.01670 = 0.02342 0.00001 -0.00186 0.00611 C10 1 0.032738 0.220276 0.440965 11.00000 0.02322 0.02133 = 0.01982 0.00326 -0.00181 0.00329 C11 1 -0.156203 0.214890 0.495985 11.00000 0.02977 0.02753 = 0.02032 0.00255 0.00241 0.00819 AFIX 43 H11 2 -0.196692 0.264800 0.526495 11.00000 -1.20000 AFIX 0 C12 1 -0.279980 0.138974 0.505493 11.00000 0.02686 0.03429 = 0.02240 0.00707 0.00458 0.00415 AFIX 43 H12 2 -0.405373 0.136467 0.542575 11.00000 -1.20000 AFIX 0 C13 1 -0.223594 0.064491 0.460921 11.00000 0.02504 0.02589 = 0.02520 0.00726 0.00095 -0.00019 AFIX 43 H13 2 -0.311268 0.011923 0.467933 11.00000 -1.20000 AFIX 0 C14 1 -0.041967 0.067292 0.407144 11.00000 0.02159 0.01987 = 0.02188 0.00328 -0.00257 0.00196 C15 1 0.011142 -0.012638 0.361008 11.00000 0.02385 0.02088 = 0.02212 0.00428 -0.00483 0.00136 C16 1 0.090242 0.144926 0.396039 11.00000 0.02065 0.02076 = 0.01873 0.00313 -0.00127 0.00278 PART -2 BR2 3 1.692852 0.728882 0.330756 10.93172 0.03806 0.02117 = 0.03972 -0.00287 -0.00605 -0.00098 PART 0 N2 4 0.830103 0.374978 0.156123 11.00000 0.02379 0.01874 = 0.02674 0.00311 0.00317 0.00271 PART -1 BR3 3 1.773956 0.729967 0.255447 10.07071 0.03439 0.02990 = 0.10263 0.01193 0.00073 -0.00265 PART 0 O3 5 0.758586 0.366146 0.269171 11.00000 0.04843 0.03005 = 0.03470 0.00935 0.01726 -0.00148 PART 1 H25 2 1.695138 0.685693 0.187400 10.93000 0.02317 PART 0 O4 5 0.914827 0.381729 0.043954 11.00000 0.04785 0.02903 = 0.02227 0.00157 -0.00017 0.00423 C17 1 0.725531 0.059314 0.089542 11.00000 0.03427 0.01991 = 0.04457 -0.00059 0.00551 0.00013 AFIX 137 H17A 2 0.879528 0.061442 0.056277 11.00000 -1.50000 H17B 2 0.576742 0.012057 0.071788 11.00000 -1.50000 H17C 2 0.823429 0.051570 0.134685 11.00000 -1.50000 AFIX 0 C18 1 0.564948 0.141661 0.098694 11.00000 0.02595 0.02149 = 0.03762 0.00097 0.00237 -0.00017 AFIX 23 H18A 2 0.459760 0.148012 0.053327 11.00000 -1.20000 H18B 2 0.409192 0.139034 0.132192 11.00000 -1.20000 AFIX 0 C19 1 0.783584 0.218586 0.125093 11.00000 0.02170 0.02175 = 0.03271 0.00285 0.00054 0.00137 AFIX 23 H19A 2 0.885378 0.213068 0.171019 11.00000 -1.20000 H19B 2 0.941906 0.220765 0.092147 11.00000 -1.20000 AFIX 0 C20 1 0.620049 0.300391 0.132416 11.00000 0.02414 0.01896 = 0.03941 0.00290 0.00096 -0.00062 AFIX 23 H20A 2 0.513741 0.305074 0.086751 11.00000 -1.20000 H20B 2 0.465211 0.298708 0.166250 11.00000 -1.20000 AFIX 0 C21 1 0.968240 0.411906 0.105781 11.00000 0.02767 0.02018 = 0.02238 0.00428 0.00135 0.00792 C22 1 1.176879 0.487416 0.130631 11.00000 0.02471 0.01917 = 0.02635 0.00594 0.00442 0.00670 C23 1 1.312142 0.526192 0.082222 11.00000 0.03141 0.03133 = 0.02797 0.00948 0.00673 0.00745 AFIX 43 H23 2 1.273739 0.503660 0.033887 11.00000 -1.20000 AFIX 0 C24 1 1.506211 0.598717 0.103759 11.00000 0.03349 0.03052 = 0.04347 0.01623 0.01054 0.00285 AFIX 43 H24 2 1.600006 0.624678 0.069886 11.00000 -1.20000 AFIX 0 C25 1 1.562775 0.632968 0.173912 11.00000 0.02793 0.02084 = 0.05202 0.01078 0.00501 0.00245 C26 1 1.423467 0.594013 0.224959 11.00000 0.02708 0.02053 = 0.03710 0.00321 -0.00022 0.00868 C27 1 1.463142 0.625104 0.297413 11.00000 0.03309 0.01913 = 0.03879 -0.00194 -0.00237 0.00377 PART 1 AFIX 43 H27 2 1.584037 0.675951 0.313799 10.06828 -1.20000 AFIX 0 PART 0 C28 1 1.334107 0.584639 0.344221 11.00000 0.04661 0.02781 = 0.02543 -0.00485 -0.00486 0.01111 AFIX 43 H28 2 1.372619 0.606130 0.392739 11.00000 -1.20000 AFIX 0 C29 1 1.142360 0.510636 0.321689 11.00000 0.04216 0.03237 = 0.02385 0.00671 0.00693 0.01063 AFIX 43 H29 2 1.050716 0.483206 0.355013 11.00000 -1.20000 AFIX 0 C30 1 1.088673 0.478472 0.251826 11.00000 0.02946 0.02073 = 0.02337 0.00360 0.00392 0.00856 C31 1 0.881596 0.403045 0.227974 11.00000 0.03131 0.02142 = 0.02728 0.00616 0.00800 0.00935 C32 1 1.230474 0.519506 0.202579 11.00000 0.02378 0.01850 = 0.02617 0.00317 0.00135 0.00806 HKLF 4 REM cu_jil050_0m_a.res in P-1 REM R1 = 0.0410 for 4759 Fo > 4sig(Fo) and 0.0420 for all 4955 data REM 376 parameters refined using 2 restraints END WGHT 0.0426 2.6902 REM Highest difference peak 0.959, deepest hole -0.809, 1-sigma level 0.082 Q1 1 -0.1648 0.3377 0.5335 11.00000 0.05 0.96 Q2 1 1.8156 0.7221 0.3004 11.00000 0.05 0.94 Q3 1 1.5262 0.6180 0.1572 11.00000 0.05 0.57 Q4 1 0.2407 0.4366 0.4774 11.00000 0.05 0.40 Q5 1 0.1270 0.2596 0.4444 11.00000 0.05 0.38 Q6 1 -0.1999 0.4663 0.5288 11.00000 0.05 0.37 Q7 1 0.6207 0.3421 0.2408 11.00000 0.05 0.37 Q8 1 1.1633 0.4996 0.2285 11.00000 0.05 0.36 Q9 1 1.4964 0.5854 0.3198 11.00000 0.05 0.35 Q10 1 0.0194 0.1050 0.4009 11.00000 0.05 0.33 Q11 1 1.7775 0.7029 0.3628 11.00000 0.05 0.31 Q12 1 1.4597 0.5930 0.2639 11.00000 0.05 0.31 Q13 1 0.0246 0.4651 0.5088 11.00000 0.05 0.30 Q14 1 1.0801 0.4574 0.1238 11.00000 0.05 0.30 Q15 1 1.7847 0.6612 0.3096 11.00000 0.05 0.29 Q16 1 1.5439 0.6334 0.2288 11.00000 0.05 0.29 Q17 1 -0.2072 0.4790 0.4544 11.00000 0.05 0.29 Q18 1 1.0491 0.4774 0.3377 11.00000 0.05 0.28 Q19 1 0.1825 0.1467 0.3677 11.00000 0.05 0.28 Q20 1 -0.1274 0.1806 0.5070 11.00000 0.05 0.28 ; _shelx_res_checksum 43205 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.11369(8) 0.39982(2) 0.48556(2) 0.03191(12) Uani 1 1 d . . . A 2 O1 O -0.1103(5) -0.07949(13) 0.36818(11) 0.0284(5) Uani 1 1 d . . . . . N1 N 0.2097(6) -0.00764(15) 0.30956(13) 0.0219(5) Uani 1 1 d . . . . . C1 C 0.0434(10) -0.1896(3) 0.0718(2) 0.0477(10) Uani 1 1 d . . . . . H1A H -0.177260 -0.186041 0.071121 0.071 Uiso 1 1 calc GR . . . . H1B H 0.089544 -0.244409 0.046014 0.071 Uiso 1 1 calc GR . . . . H1C H 0.130040 -0.144466 0.049940 0.071 Uiso 1 1 calc GR . . . . O2 O 0.5384(5) 0.06505(14) 0.25438(11) 0.0285(5) Uani 1 1 d . . . . . C2 C 0.1800(8) -0.1799(2) 0.14707(18) 0.0336(7) Uani 1 1 d . . . . . H2A H 0.401931 -0.185427 0.147360 0.040 Uiso 1 1 calc R . . . . H2B H 0.093140 -0.225894 0.168737 0.040 Uiso 1 1 calc R . . . . C3 C 0.1210(7) -0.0953(2) 0.19063(16) 0.0277(6) Uani 1 1 d . . . . . H3A H 0.199467 -0.048888 0.168143 0.033 Uiso 1 1 calc R . . . . H3B H -0.100442 -0.090657 0.192833 0.033 Uiso 1 1 calc R . . . . C4 C 0.2751(7) -0.08669(19) 0.26432(16) 0.0267(6) Uani 1 1 d . . . . . H4A H 0.205561 -0.135219 0.285403 0.032 Uiso 1 1 calc R . . . . H4B H 0.497405 -0.088450 0.261887 0.032 Uiso 1 1 calc R . . . . C5 C 0.3555(6) 0.06691(19) 0.29792(15) 0.0223(6) Uani 1 1 d . . . . . C6 C 0.2809(6) 0.14668(18) 0.34136(15) 0.0209(6) Uani 1 1 d . . . . . C7 C 0.4067(7) 0.2222(2) 0.33000(16) 0.0246(6) Uani 1 1 d . . . . . H7 H 0.533228 0.223209 0.292923 0.029 Uiso 1 1 calc R . . . . C8 C 0.3497(7) 0.29811(19) 0.37276(16) 0.0248(6) Uani 1 1 d . . . . . H8 H 0.434037 0.350385 0.364277 0.030 Uiso 1 1 calc R . . . . C9 C 0.1713(7) 0.29588(19) 0.42684(15) 0.0241(6) Uani 1 1 d . . . . . C10 C 0.0327(6) 0.22028(19) 0.44096(15) 0.0216(6) Uani 1 1 d . . . . . C11 C -0.1562(7) 0.2149(2) 0.49599(15) 0.0258(6) Uani 1 1 d . . . . . H11 H -0.196692 0.264800 0.526495 0.031 Uiso 1 1 calc R . . . . C12 C -0.2800(7) 0.1390(2) 0.50549(16) 0.0274(6) Uani 1 1 d . . . . . H12 H -0.405373 0.136467 0.542575 0.033 Uiso 1 1 calc R . . . . C13 C -0.2236(7) 0.0645(2) 0.46092(16) 0.0252(6) Uani 1 1 d . . . . . H13 H -0.311268 0.011923 0.467933 0.030 Uiso 1 1 calc R . . . . C14 C -0.0420(6) 0.06729(18) 0.40714(15) 0.0214(6) Uani 1 1 d . . . . . C15 C 0.0111(7) -0.01264(19) 0.36101(15) 0.0226(6) Uani 1 1 d . . . . . C16 C 0.0902(6) 0.14493(18) 0.39604(14) 0.0202(6) Uani 1 1 d . . . . . Br2 Br 1.69285(9) 0.72888(2) 0.33076(2) 0.03453(12) Uani 0.9317 1 d D . P B -2 N2 N 0.8301(6) 0.37498(16) 0.15612(13) 0.0231(5) Uani 1 1 d . . . . . Br3 Br 1.7740(13) 0.7300(3) 0.2554(4) 0.0560(17) Uani 0.0707 1 d D . P C -1 O3 O 0.7586(6) 0.36615(15) 0.26917(13) 0.0367(6) Uani 1 1 d . . . . . H25 H 1.695(8) 0.686(3) 0.1874(19) 0.023(9) Uiso 0.93 1 d . . P D 1 O4 O 0.9148(6) 0.38173(15) 0.04395(11) 0.0335(5) Uani 1 1 d . . . . . C17 C 0.7255(8) 0.0593(2) 0.08954(19) 0.0336(7) Uani 1 1 d . . . . . H17A H 0.879528 0.061442 0.056277 0.050 Uiso 1 1 calc GR . . . . H17B H 0.576742 0.012057 0.071788 0.050 Uiso 1 1 calc GR . . . . H17C H 0.823429 0.051570 0.134685 0.050 Uiso 1 1 calc GR . . . . C18 C 0.5649(7) 0.1417(2) 0.09869(18) 0.0289(7) Uani 1 1 d . . . . . H18A H 0.459760 0.148012 0.053327 0.035 Uiso 1 1 calc R . . . . H18B H 0.409192 0.139034 0.132192 0.035 Uiso 1 1 calc R . . . . C19 C 0.7836(7) 0.21859(19) 0.12509(17) 0.0257(6) Uani 1 1 d . . . . . H19A H 0.885378 0.213068 0.171019 0.031 Uiso 1 1 calc R . . . . H19B H 0.941906 0.220765 0.092147 0.031 Uiso 1 1 calc R . . . . C20 C 0.6200(7) 0.30039(19) 0.13242(18) 0.0279(7) Uani 1 1 d . . . . . H20A H 0.513741 0.305074 0.086751 0.033 Uiso 1 1 calc R . . . . H20B H 0.465211 0.298708 0.166250 0.033 Uiso 1 1 calc R . . . . C21 C 0.9682(7) 0.41191(19) 0.10578(15) 0.0232(6) Uani 1 1 d . . . . . C22 C 1.1769(7) 0.48742(19) 0.13063(16) 0.0229(6) Uani 1 1 d . . . . . C23 C 1.3121(7) 0.5262(2) 0.08222(17) 0.0293(7) Uani 1 1 d . . . . . H23 H 1.273739 0.503660 0.033887 0.035 Uiso 1 1 calc R . . . . C24 C 1.5062(8) 0.5987(2) 0.10376(19) 0.0343(7) Uani 1 1 d . . . . . H24 H 1.600006 0.624678 0.069886 0.041 Uiso 1 1 calc R . . . . C25 C 1.5628(7) 0.6330(2) 0.17391(19) 0.0330(7) Uani 1 1 d D . . . . C26 C 1.4235(7) 0.5940(2) 0.22496(18) 0.0284(7) Uani 1 1 d . . . . . C27 C 1.4631(7) 0.62510(19) 0.29741(18) 0.0314(7) Uani 1 1 d D . . . . H27 H 1.584037 0.675951 0.313799 0.038 Uiso 0.0683 1 calc R . P B 1 C28 C 1.3341(8) 0.5846(2) 0.34422(17) 0.0345(8) Uani 1 1 d . . . . . H28 H 1.372619 0.606130 0.392739 0.041 Uiso 1 1 calc R . . . . C29 C 1.1424(8) 0.5106(2) 0.32169(17) 0.0321(7) Uani 1 1 d . . . . . H29 H 1.050716 0.483206 0.355013 0.039 Uiso 1 1 calc R . . . . C30 C 1.0887(7) 0.47847(19) 0.25183(16) 0.0242(6) Uani 1 1 d . . . . . C31 C 0.8816(7) 0.40304(19) 0.22797(16) 0.0259(6) Uani 1 1 d . . . . . C32 C 1.2305(7) 0.51951(18) 0.20258(16) 0.0227(6) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0498(2) 0.01823(18) 0.02635(18) -0.00156(13) 0.00507(14) 0.00528(14) O1 0.0342(12) 0.0189(11) 0.0306(11) 0.0040(9) -0.0008(9) -0.0046(9) N1 0.0263(12) 0.0150(12) 0.0230(12) 0.0002(10) -0.0001(10) 0.0021(9) C1 0.054(2) 0.047(2) 0.0338(19) -0.0170(17) 0.0034(17) 0.0011(18) O2 0.0297(11) 0.0271(12) 0.0272(11) -0.0017(9) 0.0087(9) 0.0000(9) C2 0.0374(17) 0.0233(17) 0.0356(18) -0.0075(14) 0.0036(14) 0.0001(13) C3 0.0289(15) 0.0242(16) 0.0271(15) -0.0035(12) 0.0007(12) 0.0035(12) C4 0.0313(15) 0.0178(15) 0.0292(16) -0.0019(12) 0.0015(12) 0.0063(12) C5 0.0231(14) 0.0219(15) 0.0207(14) 0.0009(11) -0.0017(11) 0.0034(11) C6 0.0234(14) 0.0175(14) 0.0207(14) 0.0012(11) 0.0001(11) 0.0011(11) C7 0.0265(14) 0.0240(15) 0.0231(14) 0.0036(12) 0.0035(11) 0.0002(12) C8 0.0315(15) 0.0155(14) 0.0274(15) 0.0051(12) 0.0005(12) -0.0003(12) C9 0.0308(15) 0.0167(14) 0.0234(14) 0.0000(11) -0.0019(12) 0.0061(12) C10 0.0232(14) 0.0213(15) 0.0198(14) 0.0033(11) -0.0018(11) 0.0033(11) C11 0.0298(15) 0.0275(16) 0.0203(14) 0.0025(12) 0.0024(12) 0.0082(12) C12 0.0269(15) 0.0343(18) 0.0224(14) 0.0071(13) 0.0046(12) 0.0042(13) C13 0.0250(14) 0.0259(16) 0.0252(15) 0.0073(12) 0.0010(12) -0.0002(12) C14 0.0216(13) 0.0199(15) 0.0219(14) 0.0033(11) -0.0026(11) 0.0020(11) C15 0.0238(14) 0.0209(15) 0.0221(14) 0.0043(11) -0.0048(11) 0.0014(11) C16 0.0207(13) 0.0208(14) 0.0187(13) 0.0031(11) -0.0013(11) 0.0028(11) Br2 0.0381(2) 0.0212(2) 0.0397(2) -0.00287(15) -0.00605(16) -0.00098(15) N2 0.0238(12) 0.0187(12) 0.0267(13) 0.0031(10) 0.0032(10) 0.0027(10) Br3 0.034(3) 0.030(3) 0.103(5) 0.012(3) 0.001(3) -0.003(2) O3 0.0484(14) 0.0300(13) 0.0347(13) 0.0094(10) 0.0173(11) -0.0015(11) O4 0.0478(14) 0.0290(12) 0.0223(11) 0.0016(9) -0.0002(10) 0.0042(10) C17 0.0343(17) 0.0199(16) 0.0446(19) -0.0006(14) 0.0055(14) 0.0001(13) C18 0.0260(15) 0.0215(16) 0.0376(17) 0.0010(13) 0.0024(13) -0.0002(12) C19 0.0217(14) 0.0218(15) 0.0327(16) 0.0029(12) 0.0005(12) 0.0014(12) C20 0.0241(14) 0.0190(15) 0.0394(18) 0.0029(13) 0.0010(13) -0.0006(12) C21 0.0277(15) 0.0202(15) 0.0224(14) 0.0043(11) 0.0014(11) 0.0079(12) C22 0.0247(14) 0.0192(14) 0.0264(15) 0.0059(12) 0.0044(11) 0.0067(11) C23 0.0314(16) 0.0313(17) 0.0280(16) 0.0095(13) 0.0067(13) 0.0075(13) C24 0.0335(17) 0.0305(18) 0.0435(19) 0.0162(15) 0.0105(14) 0.0028(14) C25 0.0279(16) 0.0208(16) 0.052(2) 0.0108(15) 0.0050(14) 0.0024(13) C26 0.0271(15) 0.0205(15) 0.0371(17) 0.0032(13) -0.0002(13) 0.0087(12) C27 0.0331(16) 0.0191(15) 0.0388(18) -0.0019(13) -0.0024(14) 0.0038(13) C28 0.0466(19) 0.0278(17) 0.0254(16) -0.0049(13) -0.0049(14) 0.0111(15) C29 0.0422(18) 0.0324(18) 0.0238(15) 0.0067(13) 0.0069(13) 0.0106(14) C30 0.0295(15) 0.0207(15) 0.0234(14) 0.0036(12) 0.0039(12) 0.0086(12) C31 0.0313(15) 0.0214(15) 0.0273(15) 0.0062(12) 0.0080(12) 0.0094(12) C32 0.0238(14) 0.0185(14) 0.0262(15) 0.0032(11) 0.0013(11) 0.0081(11) 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' Br Br -0.6763 1.2805 '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' 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 C5 N1 C4 117.1(2) . . ? C15 N1 C4 118.1(2) . . ? C15 N1 C5 124.8(2) . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? C1 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C1 C2 C3 112.6(3) . . ? H2A C2 H2B 107.8 . . ? C3 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C4 C3 C2 110.7(3) . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? N1 C4 C3 112.5(2) . . ? N1 C4 H4A 109.1 . . ? N1 C4 H4B 109.1 . . ? C3 C4 H4A 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? N1 C5 C6 117.2(3) . . ? O2 C5 N1 120.5(3) . . ? O2 C5 C6 122.3(3) . . ? C7 C6 C5 119.8(3) . . ? C7 C6 C16 120.0(3) . . ? C16 C6 C5 120.2(3) . . ? C6 C7 H7 119.7 . . ? C6 C7 C8 120.5(3) . . ? C8 C7 H7 119.7 . . ? C7 C8 H8 120.4 . . ? C9 C8 C7 119.3(3) . . ? C9 C8 H8 120.4 . . ? C8 C9 Br1 117.7(2) . . ? C8 C9 C10 123.0(3) . . ? C10 C9 Br1 119.3(2) . . ? C9 C10 C11 125.0(3) . . ? C9 C10 C16 116.3(3) . . ? C16 C10 C11 118.6(3) . . ? C10 C11 H11 119.6 . . ? C12 C11 C10 120.8(3) . . ? C12 C11 H11 119.6 . . ? C11 C12 H12 119.7 . . ? C11 C12 C13 120.5(3) . . ? C13 C12 H12 119.7 . . ? C12 C13 H13 119.9 . . ? C14 C13 C12 120.3(3) . . ? C14 C13 H13 119.9 . . ? C13 C14 C15 118.7(3) . . ? C13 C14 C16 120.6(3) . . ? C16 C14 C15 120.7(3) . . ? O1 C15 N1 121.6(3) . . ? O1 C15 C14 121.5(3) . . ? N1 C15 C14 116.9(3) . . ? C6 C16 C10 120.9(3) . . ? C14 C16 C6 119.9(3) . . ? C14 C16 C10 119.2(3) . . ? C21 N2 C20 118.2(3) . . ? C31 N2 C20 117.3(3) . . ? C31 N2 C21 124.5(3) . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C18 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? C18 C17 H17C 109.5 . . ? C17 C18 H18A 109.1 . . ? C17 C18 H18B 109.1 . . ? H18A C18 H18B 107.8 . . ? C19 C18 C17 112.6(3) . . ? C19 C18 H18A 109.1 . . ? C19 C18 H18B 109.1 . . ? C18 C19 H19A 109.3 . . ? C18 C19 H19B 109.3 . . ? H19A C19 H19B 107.9 . . ? C20 C19 C18 111.8(2) . . ? C20 C19 H19A 109.3 . . ? C20 C19 H19B 109.3 . . ? N2 C20 C19 112.2(2) . . ? N2 C20 H20A 109.2 . . ? N2 C20 H20B 109.2 . . ? C19 C20 H20A 109.2 . . ? C19 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? N2 C21 C22 117.4(3) . . ? O4 C21 N2 119.9(3) . . ? O4 C21 C22 122.7(3) . . ? C23 C22 C21 118.8(3) . . ? C23 C22 C32 120.9(3) . . ? C32 C22 C21 120.3(3) . . ? C22 C23 H23 119.8 . . ? C22 C23 C24 120.4(3) . . ? C24 C23 H23 119.8 . . ? C23 C24 H24 119.7 . . ? C25 C24 C23 120.7(3) . . ? C25 C24 H24 119.7 . . ? Br3 C25 H25 32(2) . . ? C24 C25 Br3 150.3(3) . . ? C24 C25 H25 119(2) . . ? C24 C25 C26 119.9(3) . . ? C26 C25 Br3 89.8(3) . . ? C26 C25 H25 121(2) . . ? C27 C26 C25 123.9(3) . . ? C27 C26 C32 117.1(3) . . ? C32 C26 C25 119.0(3) . . ? C26 C27 Br2 119.5(3) . . ? C26 C27 H27 119.0 . . ? C28 C27 Br2 118.5(3) . . ? C28 C27 C26 121.9(3) . . ? C28 C27 H27 119.0 . . ? C27 C28 H28 119.6 . . ? C27 C28 C29 120.7(3) . . ? C29 C28 H28 119.6 . . ? C28 C29 H29 120.0 . . ? C30 C29 C28 120.1(3) . . ? C30 C29 H29 120.0 . . ? C29 C30 C31 120.3(3) . . ? C29 C30 C32 119.4(3) . . ? C32 C30 C31 120.3(3) . . ? N2 C31 C30 117.4(3) . . ? O3 C31 N2 120.9(3) . . ? O3 C31 C30 121.7(3) . . ? C22 C32 C26 119.2(3) . . ? C22 C32 C30 120.1(3) . . ? C30 C32 C26 120.8(3) . . ? 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 BR1b C9 1.903(3) . ? O1 C15 1.215(4) . ? N1 C4 1.477(4) . ? N1 C5 1.397(4) . ? N1 C15 1.394(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C1 C2 1.522(5) . ? O2 C5 1.216(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.526(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.523(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.482(4) . ? C6 C7 1.373(4) . ? C6 C16 1.413(4) . ? C7 H7 0.9500 . ? C7 C8 1.405(4) . ? C8 H8 0.9500 . ? C8 C9 1.370(4) . ? C9 C10 1.415(4) . ? C10 C11 1.422(4) . ? C10 C16 1.419(4) . ? C11 H11 0.9500 . ? C11 C12 1.363(5) . ? C12 H12 0.9500 . ? C12 C13 1.404(5) . ? C13 H13 0.9500 . ? C13 C14 1.375(4) . ? C14 C15 1.482(4) . ? C14 C16 1.412(4) . ? Br2 C27 1.902(3) . ? N2 C20 1.470(4) . ? N2 C21 1.395(4) . ? N2 C31 1.395(4) . ? Br3 C25 2.153(6) . ? O3 C31 1.222(4) . ? O4 C21 1.222(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C17 C18 1.526(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C18 C19 1.526(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C19 C20 1.526(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.480(4) . ? C22 C23 1.375(4) . ? C22 C32 1.408(4) . ? C23 H23 0.9500 . ? C23 C24 1.400(5) . ? C24 H24 0.9500 . ? C24 C25 1.384(5) . ? C25 H25 0.99(4) . ? C25 C26 1.426(5) . ? C26 C27 1.411(5) . ? C26 C32 1.424(4) . ? C27 H27 0.9500 . ? C27 C28 1.353(5) . ? C28 H28 0.9500 . ? C28 C29 1.415(5) . ? C29 H29 0.9500 . ? C29 C30 1.371(4) . ? C30 C31 1.473(5) . ? C30 C32 1.422(4) . ?