#------------------------------------------------------------------------------ #$Date: 2020-06-05 14:30:58 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252925 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157471.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_7157471 loop_ _publ_author_name 'Calatrava-P\'erez, Elena' 'Acherman, Stefan' 'Stricker, Lucas' 'McManus, Gavin' 'Delente, Jason' 'Lynes, Amy D.' 'Henwood, Adam F.' 'Lovitt, June I.' 'Hawes, Chris S.' 'Byrne, Kevin' 'Schmitt, Wolfgang' 'Kotova, Oxana' 'Gunnlaugsson, Thorfinnur' 'Scanlan, Eoin M.' _publ_section_title ; Fluorescent supramolecular hierarchical self-assemblies from glycosylated 4-amino- and 4-bromo-1,8-naphthalimides. ; _journal_issue 18 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3475 _journal_page_last 3480 _journal_paper_doi 10.1039/d0ob00033g _journal_volume 18 _journal_year 2020 _chemical_formula_moiety 'C20 H22 Br N O2' _chemical_formula_sum 'C20 H22 Br N O2' _chemical_formula_weight 388.29 _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 geom _atom_sites_solution_primary dual _audit_creation_date 2017-10-31 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2019-11-28 deposited with the CCDC. 2020-04-15 downloaded from the CCDC. ; _cell_angle_alpha 81.534(3) _cell_angle_beta 86.654(4) _cell_angle_gamma 84.890(3) _cell_formula_units_Z 2 _cell_length_a 4.6972(2) _cell_length_b 11.9618(5) _cell_length_c 15.7954(7) _cell_measurement_reflns_used 2912 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 67.85 _cell_measurement_theta_min 3.75 _cell_volume 873.41(7) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _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 100.0 _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_unetI/netI 0.0565 _diffrn_reflns_Laue_measured_fraction_full 0.983 _diffrn_reflns_Laue_measured_fraction_max 0.978 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 7358 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.978 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.319 _diffrn_reflns_theta_min 3.748 _diffrn_source 'sealed tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 3.296 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_correction_T_min 0.5220 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0825 before and 0.0554 after correction. The Ratio of minimum to maximum transmission is 0.6931. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.476 _exptl_crystal_description plate _exptl_crystal_F_000 400 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _refine_diff_density_max 1.239 _refine_diff_density_min -0.610 _refine_diff_density_rms 0.140 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 3139 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.136 _refine_ls_R_factor_all 0.0839 _refine_ls_R_factor_gt 0.0732 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1140P)^2^+0.9070P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1867 _refine_ls_wR_factor_ref 0.1935 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2664 _reflns_number_total 3139 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00033g2.cif _cod_data_source_block 8 _cod_depositor_comments 'Adding full bibliography for 7157470--7157472.cif.' _cod_database_code 7157471 _shelx_shelxl_version_number 2014/7 _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 0.937 _shelx_estimated_absorpt_t_min 0.655 _olex2_refinement_description ; 1. Others Fixed Sof: Br1(0.93) Br2(0.07) H13(0.07) H15(0.93) Fixed Uiso: H1A(0.081) H1B(0.081) H1C(0.081) H2A(0.055) H2B(0.055) H3A(0.05) H3B(0.05) H4A(0.048) H4B(0.048) H5A(0.046) H5B(0.046) H6A(0.045) H6B(0.045) H7A(0.041) H7B(0.041) H8A(0.036) H8B(0.036) H11(0.039) H12(0.042) H13(0.041) H15(0.04) H16(0.041) H17(0.038) Fixed X: H1A(1.0701) H1B(1.1872) H1C(0.8826) H2A(1.0007) H2B(0.6939) H3A(0.675) H3B(0.9841) H4A(0.4785) H4B(0.7882) H5A(0.8038) H5B(0.4899) H6A(0.5925) H6B(0.2869) H7A(0.4306) H7B(0.7026) H8A(0.3492) H8B(0.1175) H11(0.1265) H12(0.2409) H13(0.5477) H15(0.8681) H16(1.0587) H17(0.9447) Fixed Y: H1A(0.8801) H1B(0.8277) H1C(0.8992) H2A(0.6887) H2B(0.7582) H3A(0.724) H3B(0.6563) H4A(0.5818) H4B(0.5157) H5A(0.4825) H5B(0.5451) H6A(0.345) H6B(0.4011) H7A(0.2348) H7B(0.2945) H8A(0.4422) H8B(0.3522) H11(0.0201) H12(-0.0616) H13(0.0217) H15(0.1812) H16(0.3471) H17(0.4237) Fixed Z: H1A(-0.0491) H1B(0.0427) H1C(0.0363) H2A(-0.0276) H2B(-0.0252) H3A(0.127) H3B(0.1254) H4A(0.0652) H4B(0.0566) H5A(0.2096) H5B(0.2166) H6A(0.1376) H6B(0.1662) H7A(0.2627) H7B(0.2852) H8A(0.3337) H8B(0.3325) H11(0.5543) H12(0.6931) H13(0.7673) H15(0.7761) H16(0.7099) H17(0.5702) ; _shelx_res_file ; cu_csh276_0m.res created by SHELXL-2014/7 TITL cu_csh276_0m_a.res in P-1 REM Old TITL cu_CSH276_0m in P-1 REM SHELXT solution in P-1 REM R1 0.155, Rweak 0.015, Alpha 0.064, Orientation as input REM Formula found by SHELXT: C21 N O2 Br CELL 1.54178 4.6972 11.9618 15.7954 81.534 86.654 84.89 ZERR 2 0.0002 0.0005 0.0007 0.003 0.004 0.003 LATT 1 SFAC C H Br N O UNIT 40 44 2 2 4 L.S. 10 PLAN 20 SIZE 0.02 0.08 0.14 TEMP -173.15 BOND $H list 4 fmap 2 ACTA OMIT -4 8 1 REM REM REM WGHT 0.114000 0.907000 FVAR 0.53192 PART 1 BR1 3 0.594546 -0.013352 0.824118 10.93000 0.05624 0.02641 = 0.04242 0.00188 -0.00658 -0.00509 PART 0 PART 2 BR2 3 0.849126 0.123046 0.835784 10.07000 0.04980 0.04130 = 0.05750 -0.01654 -0.01438 -0.00548 PART 0 O1 5 0.107031 0.167150 0.419635 11.00000 0.03370 0.02552 = 0.04419 -0.00236 -0.00567 -0.00863 O2 5 0.711554 0.440971 0.428443 11.00000 0.03296 0.01941 = 0.04788 -0.00314 0.00090 -0.00584 N1 4 0.399729 0.306480 0.425501 11.00000 0.02643 0.01611 = 0.04354 -0.00165 -0.00218 -0.00498 PART 1 C1 1 1.015750 0.845797 0.009158 11.00000 0.07072 0.03790 = 0.05100 0.00388 -0.00352 -0.01171 AFIX 137 H1A 2 1.070061 0.880131 -0.049096 11.00000 -1.50000 H1B 2 1.187152 0.827732 0.042683 11.00000 -1.50000 H1C 2 0.882593 0.899191 0.036255 11.00000 -1.50000 AFIX 0 PART 0 C2 1 0.873449 0.738695 0.005515 11.00000 0.06230 0.03179 = 0.04194 0.00038 -0.00072 -0.00151 AFIX 23 H2A 2 1.000723 0.688685 -0.027563 11.00000 -1.20000 H2B 2 0.693896 0.758201 -0.025174 11.00000 -1.20000 AFIX 0 C3 1 0.804771 0.674160 0.094411 11.00000 0.05107 0.03059 = 0.04218 -0.00290 -0.00028 -0.00222 AFIX 23 H3A 2 0.675046 0.723984 0.126978 11.00000 -1.20000 H3B 2 0.984099 0.656320 0.125405 11.00000 -1.20000 AFIX 0 C4 1 0.665024 0.563796 0.092275 11.00000 0.04516 0.02814 = 0.04686 -0.00713 -0.00016 0.00047 AFIX 23 H4A 2 0.478526 0.581750 0.065164 11.00000 -1.20000 H4B 2 0.788176 0.515721 0.056644 11.00000 -1.20000 AFIX 0 C5 1 0.617887 0.497479 0.181837 11.00000 0.04511 0.02651 = 0.04271 -0.00329 -0.00276 -0.00125 AFIX 23 H5A 2 0.803792 0.482470 0.209562 11.00000 -1.20000 H5B 2 0.489931 0.545055 0.216649 11.00000 -1.20000 AFIX 0 C6 1 0.489040 0.385610 0.181919 11.00000 0.04270 0.02837 = 0.04249 -0.00804 -0.00253 -0.00185 AFIX 23 H6A 2 0.592491 0.344965 0.137638 11.00000 -1.20000 H6B 2 0.286922 0.401150 0.166192 11.00000 -1.20000 AFIX 0 C7 1 0.501124 0.308675 0.268631 11.00000 0.03648 0.01778 = 0.04868 -0.00693 -0.00009 -0.00220 AFIX 23 H7A 2 0.430566 0.234779 0.262704 11.00000 -1.20000 H7B 2 0.702580 0.294535 0.285221 11.00000 -1.20000 AFIX 0 C8 1 0.322454 0.360228 0.339561 11.00000 0.02711 0.01819 = 0.04348 -0.00275 -0.00070 -0.00356 AFIX 23 H8A 2 0.349180 0.442223 0.333673 11.00000 -1.20000 H8B 2 0.117539 0.352212 0.332519 11.00000 -1.20000 AFIX 0 C9 1 0.276390 0.206182 0.460433 11.00000 0.02342 0.01642 = 0.04447 -0.00557 0.00200 -0.00398 C10 1 0.361767 0.154439 0.546554 11.00000 0.02594 0.01484 = 0.04391 -0.00584 0.00099 -0.00331 C11 1 0.252222 0.055694 0.584887 11.00000 0.03590 0.01986 = 0.04425 -0.00775 0.00035 -0.00904 AFIX 43 H11 2 0.126519 0.020104 0.554269 11.00000 -1.20000 AFIX 0 C12 1 0.320679 0.006303 0.667578 11.00000 0.03015 0.01736 = 0.05373 -0.00030 0.00597 0.00130 AFIX 43 H12 2 0.240949 -0.061597 0.693086 11.00000 -1.20000 AFIX 0 C13 1 0.502241 0.056268 0.711134 11.00000 0.04127 0.02362 = 0.03594 0.00188 -0.00354 0.00236 PART 2 AFIX 43 H13 2 0.547667 0.021730 0.767329 10.07000 -1.20000 AFIX 0 PART 0 C14 1 0.627858 0.158095 0.676504 11.00000 0.02575 0.02169 = 0.04665 -0.00827 -0.00163 0.00259 C15 1 0.817816 0.212335 0.719560 11.00000 0.02999 0.02710 = 0.04230 -0.00834 -0.00312 0.00202 PART 1 AFIX 43 H15 2 0.868064 0.181201 0.776081 10.93000 -1.20000 AFIX 0 PART 0 C16 1 0.932011 0.310818 0.680071 11.00000 0.02876 0.02389 = 0.05186 -0.01432 -0.00466 -0.00140 AFIX 43 H16 2 1.058658 0.347055 0.709898 11.00000 -1.20000 AFIX 0 C17 1 0.862406 0.356952 0.597054 11.00000 0.02970 0.02024 = 0.04660 -0.00880 0.00131 -0.00587 AFIX 43 H17 2 0.944721 0.423685 0.570229 11.00000 -1.20000 AFIX 0 C18 1 0.674697 0.306549 0.553337 11.00000 0.02404 0.01737 = 0.04549 -0.00817 -0.00014 -0.00165 C19 1 0.604767 0.356788 0.465956 11.00000 0.02485 0.01720 = 0.04339 -0.00777 -0.00033 -0.00109 C20 1 0.554888 0.205538 0.592300 11.00000 0.02656 0.01710 = 0.04252 -0.00604 0.00058 -0.00046 HKLF 4 REM cu_csh276_0m_a.res in P-1 REM R1 = 0.0732 for 2664 Fo > 4sig(Fo) and 0.0839 for all 3139 data REM 227 parameters refined using 0 restraints END WGHT 0.1161 0.8188 REM Highest difference peak 1.239, deepest hole -0.610, 1-sigma level 0.140 Q1 1 0.4362 -0.0333 0.8026 11.00000 0.05 1.22 Q2 1 0.7481 0.0151 0.8454 11.00000 0.05 1.05 Q3 1 0.6045 -0.0216 0.8809 11.00000 0.05 1.04 Q4 1 0.3477 0.0170 0.7113 11.00000 0.05 0.67 Q5 1 0.4876 0.1724 0.5578 11.00000 0.05 0.66 Q6 1 0.5272 0.3280 0.4320 11.00000 0.05 0.50 Q7 1 0.7459 0.3336 0.5827 11.00000 0.05 0.49 Q8 1 0.7544 0.1781 0.6842 11.00000 0.05 0.47 Q9 1 0.2303 0.1827 0.4255 11.00000 0.05 0.47 Q10 1 0.5480 0.1252 0.6992 11.00000 0.05 0.43 Q11 1 0.6568 0.1664 0.7186 11.00000 0.05 0.43 Q12 1 0.6382 0.2780 0.5611 11.00000 0.05 0.40 Q13 1 0.3905 0.2482 0.4484 11.00000 0.05 0.39 Q14 1 0.3430 0.1012 0.5634 11.00000 0.05 0.38 Q15 1 0.7672 0.4039 0.4584 11.00000 0.05 0.35 Q16 1 0.8805 0.4567 0.4569 11.00000 0.05 0.33 Q17 1 0.1161 0.1420 0.4593 11.00000 0.05 0.33 Q18 1 0.6412 0.3916 0.4006 11.00000 0.05 0.33 Q19 1 0.6565 0.1670 0.6245 11.00000 0.05 0.32 Q20 1 0.7967 0.7121 -0.0426 11.00000 0.05 0.32 ; _shelx_res_checksum 80325 _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 0.59455(15) -0.01335(5) 0.82412(4) 0.0421(3) Uani 0.93 1 d . . P A 1 Br2 Br 0.8491(19) 0.1230(8) 0.8358(6) 0.0480(19) Uani 0.07 1 d . . P B 2 O1 O 0.1070(7) 0.1671(3) 0.4196(2) 0.0342(8) Uani 1 1 d . . . . . O2 O 0.7116(7) 0.4410(3) 0.4284(2) 0.0335(8) Uani 1 1 d . . . . . N1 N 0.3997(8) 0.3065(3) 0.4255(3) 0.0287(8) Uani 1 1 d . . . . . C1 C 1.0157(16) 0.8458(6) 0.0092(4) 0.0538(15) Uani 1 1 d . . . C 1 H1A H 1.0701 0.8801 -0.0491 0.081 Uiso 1 1 calc GR . . C 1 H1B H 1.1872 0.8277 0.0427 0.081 Uiso 1 1 calc GR . . C 1 H1C H 0.8826 0.8992 0.0363 0.081 Uiso 1 1 calc GR . . C 1 C2 C 0.8734(14) 0.7387(5) 0.0055(4) 0.0461(13) Uani 1 1 d . . . . . H2A H 1.0007 0.6887 -0.0276 0.055 Uiso 1 1 calc R . . C . H2B H 0.6939 0.7582 -0.0252 0.055 Uiso 1 1 calc R . . C . C3 C 0.8048(13) 0.6742(5) 0.0944(4) 0.0417(12) Uani 1 1 d . . . . . H3A H 0.6750 0.7240 0.1270 0.050 Uiso 1 1 calc R . . . . H3B H 0.9841 0.6563 0.1254 0.050 Uiso 1 1 calc R . . . . C4 C 0.6650(12) 0.5638(5) 0.0923(4) 0.0402(12) Uani 1 1 d . . . . . H4A H 0.4785 0.5818 0.0652 0.048 Uiso 1 1 calc R . . . . H4B H 0.7882 0.5157 0.0566 0.048 Uiso 1 1 calc R . . . . C5 C 0.6179(12) 0.4975(5) 0.1818(3) 0.0384(11) Uani 1 1 d . . . . . H5A H 0.8038 0.4825 0.2096 0.046 Uiso 1 1 calc R . . . . H5B H 0.4899 0.5451 0.2166 0.046 Uiso 1 1 calc R . . . . C6 C 0.4890(12) 0.3856(5) 0.1819(3) 0.0376(11) Uani 1 1 d . . . . . H6A H 0.5925 0.3450 0.1376 0.045 Uiso 1 1 calc R . . . . H6B H 0.2869 0.4011 0.1662 0.045 Uiso 1 1 calc R . . . . C7 C 0.5011(11) 0.3087(4) 0.2686(3) 0.0342(11) Uani 1 1 d . . . . . H7A H 0.4306 0.2348 0.2627 0.041 Uiso 1 1 calc R . . . . H7B H 0.7026 0.2945 0.2852 0.041 Uiso 1 1 calc R . . . . C8 C 0.3225(10) 0.3602(4) 0.3396(3) 0.0297(10) Uani 1 1 d . . . . . H8A H 0.3492 0.4422 0.3337 0.036 Uiso 1 1 calc R . . . . H8B H 0.1175 0.3522 0.3325 0.036 Uiso 1 1 calc R . . . . C9 C 0.2764(9) 0.2062(4) 0.4604(3) 0.0280(10) Uani 1 1 d . . . . . C10 C 0.3618(10) 0.1544(4) 0.5466(3) 0.0281(9) Uani 1 1 d . . . . . C11 C 0.2522(11) 0.0557(4) 0.5849(3) 0.0327(10) Uani 1 1 d . . . . . H11 H 0.1265 0.0201 0.5543 0.039 Uiso 1 1 calc R . . . . C12 C 0.3207(10) 0.0063(4) 0.6676(4) 0.0347(11) Uani 1 1 d . . . . . H12 H 0.2409 -0.0616 0.6931 0.042 Uiso 1 1 calc R . . . . C13 C 0.5022(11) 0.0563(4) 0.7111(3) 0.0345(11) Uani 1 1 d . . . . . H13 H 0.5477 0.0217 0.7673 0.041 Uiso 0.07 1 calc R . P A 2 C14 C 0.6279(10) 0.1581(4) 0.6765(3) 0.0313(10) Uani 1 1 d . . . . . C15 C 0.8178(10) 0.2123(4) 0.7196(3) 0.0330(10) Uani 1 1 d . . . . . H15 H 0.8681 0.1812 0.7761 0.040 Uiso 0.93 1 calc R . P B 1 C16 C 0.9320(10) 0.3108(4) 0.6801(4) 0.0339(11) Uani 1 1 d . . . . . H16 H 1.0587 0.3471 0.7099 0.041 Uiso 1 1 calc R . . . . C17 C 0.8624(10) 0.3570(4) 0.5971(3) 0.0317(10) Uani 1 1 d . . . . . H17 H 0.9447 0.4237 0.5702 0.038 Uiso 1 1 calc R . . . . C18 C 0.6747(9) 0.3065(4) 0.5533(3) 0.0287(10) Uani 1 1 d . . . . . C19 C 0.6048(10) 0.3568(4) 0.4660(3) 0.0282(9) Uani 1 1 d . . . . . C20 C 0.5549(10) 0.2055(4) 0.5923(3) 0.0287(10) 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 0.0562(4) 0.0264(4) 0.0424(4) 0.0019(2) -0.0066(2) -0.0051(2) Br2 0.050(4) 0.041(5) 0.057(5) -0.017(4) -0.014(4) -0.005(4) O1 0.0337(17) 0.0255(18) 0.0442(19) -0.0024(14) -0.0057(14) -0.0086(14) O2 0.0330(17) 0.0194(17) 0.0479(19) -0.0031(14) 0.0009(15) -0.0058(13) N1 0.0264(18) 0.0161(19) 0.044(2) -0.0017(16) -0.0022(16) -0.0050(15) C1 0.071(4) 0.038(3) 0.051(3) 0.004(3) -0.004(3) -0.012(3) C2 0.062(4) 0.032(3) 0.042(3) 0.000(2) -0.001(3) -0.002(3) C3 0.051(3) 0.031(3) 0.042(3) -0.003(2) 0.000(2) -0.002(2) C4 0.045(3) 0.028(3) 0.047(3) -0.007(2) 0.000(2) 0.000(2) C5 0.045(3) 0.027(3) 0.043(3) -0.003(2) -0.003(2) -0.001(2) C6 0.043(3) 0.028(3) 0.042(3) -0.008(2) -0.003(2) -0.002(2) C7 0.036(2) 0.018(2) 0.049(3) -0.007(2) 0.000(2) -0.0022(18) C8 0.027(2) 0.018(2) 0.043(3) -0.0027(19) -0.0007(19) -0.0036(17) C9 0.023(2) 0.016(2) 0.044(3) -0.0056(19) 0.0020(18) -0.0040(17) C10 0.026(2) 0.015(2) 0.044(3) -0.0058(18) 0.0010(18) -0.0033(17) C11 0.036(2) 0.020(2) 0.044(3) -0.008(2) 0.000(2) -0.0090(19) C12 0.030(2) 0.017(2) 0.054(3) 0.000(2) 0.006(2) 0.0013(18) C13 0.041(3) 0.024(2) 0.036(2) 0.0019(19) -0.004(2) 0.002(2) C14 0.026(2) 0.022(2) 0.047(3) -0.008(2) -0.0016(19) 0.0026(18) C15 0.030(2) 0.027(3) 0.042(3) -0.008(2) -0.0031(19) 0.0020(19) C16 0.029(2) 0.024(2) 0.052(3) -0.014(2) -0.005(2) -0.0014(18) C17 0.030(2) 0.020(2) 0.047(3) -0.0088(19) 0.0013(19) -0.0059(18) C18 0.024(2) 0.017(2) 0.045(3) -0.0082(19) -0.0001(18) -0.0016(17) C19 0.025(2) 0.017(2) 0.043(3) -0.0078(18) -0.0003(18) -0.0011(17) C20 0.027(2) 0.017(2) 0.043(3) -0.0060(18) 0.0006(18) -0.0005(17) 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 C9 N1 C8 118.4(4) . . ? C9 N1 C19 124.3(4) . . ? C19 N1 C8 117.2(4) . . ? 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 109.0 . . ? C1 C2 H2B 109.0 . . ? C1 C2 C3 112.8(5) . . ? H2A C2 H2B 107.8 . . ? C3 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? C2 C3 H3A 108.8 . . ? C2 C3 H3B 108.8 . . ? C2 C3 C4 113.8(5) . . ? H3A C3 H3B 107.7 . . ? C4 C3 H3A 108.8 . . ? C4 C3 H3B 108.8 . . ? C3 C4 H4A 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.9 . . ? C5 C4 C3 112.4(5) . . ? C5 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C4 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C6 C5 C4 113.8(5) . . ? C6 C5 H5A 108.8 . . ? C6 C5 H5B 108.8 . . ? C5 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C5 C6 C7 113.4(4) . . ? H6A C6 H6B 107.7 . . ? C7 C6 H6A 108.9 . . ? C7 C6 H6B 108.9 . . ? C6 C7 H7A 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C8 C7 C6 112.6(4) . . ? C8 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? N1 C8 C7 112.6(4) . . ? N1 C8 H8A 109.1 . . ? N1 C8 H8B 109.1 . . ? C7 C8 H8A 109.1 . . ? C7 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? O1 C9 N1 119.7(5) . . ? O1 C9 C10 123.7(4) . . ? N1 C9 C10 116.6(4) . . ? C11 C10 C9 120.2(4) . . ? C11 C10 C20 118.6(5) . . ? C20 C10 C9 121.2(4) . . ? C10 C11 H11 119.1 . . ? C10 C11 C12 121.8(5) . . ? C12 C11 H11 119.1 . . ? C11 C12 H12 120.4 . . ? C13 C12 C11 119.3(5) . . ? C13 C12 H12 120.4 . . ? C12 C13 Br1 118.5(4) . . ? C12 C13 H13 118.5 . . ? C12 C13 C14 123.0(5) . . ? C14 C13 Br1 118.5(4) . . ? C14 C13 H13 118.5 . . ? C15 C14 C13 124.7(5) . . ? C15 C14 C20 119.1(5) . . ? C20 C14 C13 116.2(4) . . ? C14 C15 Br2 106.2(4) . . ? C14 C15 H15 119.8 . . ? C16 C15 Br2 133.3(5) . . ? C16 C15 C14 120.5(5) . . ? C16 C15 H15 119.8 . . ? C15 C16 H16 119.8 . . ? C15 C16 C17 120.4(5) . . ? C17 C16 H16 119.8 . . ? C16 C17 H17 119.7 . . ? C18 C17 C16 120.5(5) . . ? C18 C17 H17 119.7 . . ? C17 C18 C19 119.5(4) . . ? C17 C18 C20 120.1(5) . . ? C20 C18 C19 120.4(4) . . ? O2 C19 N1 119.6(5) . . ? O2 C19 C18 122.7(4) . . ? N1 C19 C18 117.6(4) . . ? C14 C20 C10 121.2(4) . . ? C14 C20 C18 119.3(4) . . ? C18 C20 C10 119.6(5) . . ? 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 C13 1.912(5) . ? Br2 C15 1.990(11) . ? O1 C9 1.217(6) . ? O2 C19 1.223(6) . ? N1 C8 1.465(6) . ? N1 C9 1.404(6) . ? N1 C19 1.409(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C1 C2 1.507(9) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.531(8) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.531(8) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.531(8) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C6 1.517(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.535(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C8 1.530(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.472(7) . ? C10 C11 1.374(7) . ? C10 C20 1.423(7) . ? C11 H11 0.9500 . ? C11 C12 1.395(8) . ? C12 H12 0.9500 . ? C12 C13 1.356(8) . ? C13 H13 0.9500 . ? C13 C14 1.423(7) . ? C14 C15 1.408(7) . ? C14 C20 1.416(7) . ? C15 H15 0.9500 . ? C15 C16 1.386(8) . ? C16 H16 0.9500 . ? C16 C17 1.391(8) . ? C17 H17 0.9500 . ? C17 C18 1.381(7) . ? C18 C19 1.465(7) . ? C18 C20 1.420(7) . ?