#------------------------------------------------------------------------------ #$Date: 2022-02-04 21:56:07 +0200 (Fri, 04 Feb 2022) $ #$Revision: 272732 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061088.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_7061088 loop_ _publ_author_name 'Wang, Rui' 'Zhang, Wei' 'Tang, Ying' 'Qi, Ze-Hui' 'Yu, Yuan-Hui' 'Tan, Hong-Bo' 'Tang, Dian-Yong' 'Xu, Zhi-Gang' 'Chen, Zhong-Zhu' _publ_section_title ; A four-component domino reaction for the synthesis of novel bridgehead nitrogen-containing pyrido[1,2-d][1,4]diazepines ; _journal_issue 2 _journal_name_full 'New Journal of Chemistry' _journal_page_first 592 _journal_page_last 598 _journal_paper_doi 10.1039/D1NJ04233E _journal_volume 46 _journal_year 2022 _chemical_formula_sum 'C24 H27 Br N2 O6' _chemical_formula_weight 519.38 _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 geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-07-26 deposited with the CCDC. 2021-11-26 downloaded from the CCDC. ; _cell_angle_alpha 105.831(2) _cell_angle_beta 108.602(2) _cell_angle_gamma 98.017(2) _cell_formula_units_Z 2 _cell_length_a 10.1274(13) _cell_length_b 10.9703(14) _cell_length_c 11.7010(15) _cell_measurement_reflns_used 3666 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.54 _cell_measurement_theta_min 2.57 _cell_volume 1148.2(3) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0124 _diffrn_reflns_av_unetI/netI 0.0229 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6423 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.995 _diffrn_reflns_theta_min 2.986 _exptl_absorpt_coefficient_mu 1.834 _exptl_absorpt_correction_type none _exptl_crystal_colour COLORLESS _exptl_crystal_density_diffrn 1.502 _exptl_crystal_description BLOCK _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.230 _exptl_crystal_size_min 0.190 _refine_diff_density_max 0.222 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 302 _refine_ls_number_reflns 4470 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0293 _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^)+(0.0439P)^2^+0.2714P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0766 _refine_ls_wR_factor_ref 0.0803 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3760 _reflns_number_total 4470 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj04233e2.cif _cod_data_source_block 1 _cod_depositor_comments 'Adding full bibliography for 7061088--7061090.cif.' _cod_database_code 7061088 _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_res_file ; 1.res created by SHELXL-2014/7 TITL 1_a.res in P-1 CELL 0.71073 10.1274 10.9703 11.701 105.831 108.602 98.017 ZERR 2 0.0013 0.0014 0.0015 0.002 0.002 0.002 LATT 1 SFAC C H Br N O UNIT 48 54 2 4 12 OMIT 1 -1 1 OMIT 0 -1 1 OMIT -3 1 1 OMIT -2 2 0 OMIT -3.00 52.00 L.S. 25 ACTA BOND $H FMAP 2 PLAN 20 LIST 4 CONF HTAB HTAB O5 O4 HTAB N2 O2 EQIV $1 x+1, y+1, z HTAB C7 Br1_$1 EQIV $2 x-1, y-1, z HTAB C23 O2_$2 EQIV $3 -x+1, -y+1, -z HTAB C12 O3_$3 HTAB C12 O3 EQIV $4 -x+1, -y+1, -z+1 HTAB C15 O1_$4 TEMP 23 WGHT 0.043900 0.271400 FVAR 0.50750 BR1 3 0.182629 -0.067470 0.333340 11.00000 0.05496 0.04497 = 0.05611 0.01402 0.00730 -0.01557 O002 5 0.240508 0.271053 0.117911 11.00000 0.02552 0.07271 = 0.03177 0.02337 0.00528 0.00056 O4 5 0.761833 0.398395 0.616398 11.00000 0.03195 0.06353 = 0.02867 0.02064 0.00213 -0.00738 O1 5 1.147626 0.863973 0.852519 11.00000 0.04201 0.05635 = 0.03340 0.00380 0.01196 -0.01175 O2 5 1.184235 0.860314 0.672577 11.00000 0.05030 0.05375 = 0.04468 0.01485 0.01983 -0.01137 O3 5 0.323431 0.297157 -0.029951 11.00000 0.04160 0.08376 = 0.02677 0.02251 0.00521 -0.00512 N1 4 0.739785 0.436079 0.274376 11.00000 0.02621 0.03340 = 0.02617 0.01135 0.01260 0.00339 O5 5 0.651614 0.356561 0.773506 11.00000 0.05256 0.06749 = 0.02310 0.01244 0.00789 -0.01125 AFIX 147 H5 2 0.714755 0.386963 0.752001 11.00000 -1.50000 AFIX 0 N2 4 0.960860 0.710897 0.450816 11.00000 0.04076 0.04581 = 0.03370 0.01218 0.01458 -0.01002 AFIX 43 H2 2 1.043716 0.765665 0.484522 11.00000 -1.20000 AFIX 0 C17 1 0.496776 0.325972 0.302879 11.00000 0.02609 0.03099 = 0.02702 0.01208 0.01048 0.00234 AFIX 43 H17 2 0.413648 0.284716 0.308658 11.00000 -1.20000 AFIX 0 C21 1 0.433862 0.141126 0.445610 11.00000 0.03525 0.03238 = 0.02771 0.01439 0.01004 0.00540 AFIX 43 H21 2 0.432095 0.121095 0.362529 11.00000 -1.20000 AFIX 0 C11 1 0.616041 0.394646 0.173115 11.00000 0.03271 0.02720 = 0.02553 0.00972 0.01289 0.00669 C9 1 0.746623 0.456327 0.406151 11.00000 0.02313 0.03222 = 0.02321 0.01178 0.00827 0.00367 AFIX 13 H9 2 0.835709 0.437981 0.454335 11.00000 -1.20000 AFIX 0 C18 1 0.621449 0.363832 0.405613 11.00000 0.02581 0.03125 = 0.02409 0.01107 0.00980 0.00300 C14 1 0.347956 0.304777 0.080000 11.00000 0.03263 0.03525 = 0.02771 0.01302 0.00854 0.00205 C5 1 0.895697 0.692000 0.530538 11.00000 0.03449 0.02762 = 0.03606 0.01244 0.01524 0.00525 C13 1 0.487910 0.346901 0.185991 11.00000 0.02779 0.03028 = 0.02266 0.01043 0.00746 0.00323 C20 1 0.541021 0.245175 0.544448 11.00000 0.02855 0.03650 = 0.02623 0.01663 0.00913 0.00666 C19 1 0.646136 0.336385 0.524231 11.00000 0.02541 0.03840 = 0.02494 0.01274 0.00677 0.00310 C10 1 0.749405 0.599667 0.472742 11.00000 0.03010 0.03568 = 0.03012 0.01122 0.01392 0.00569 AFIX 23 H10A 2 0.685936 0.629611 0.410594 11.00000 -1.20000 H10B 2 0.711709 0.602674 0.539700 11.00000 -1.20000 AFIX 0 C4 1 0.959561 0.748885 0.659925 11.00000 0.04029 0.03387 = 0.03370 0.00821 0.01816 0.00069 AFIX 43 H4 2 0.906977 0.735454 0.709569 11.00000 -1.20000 AFIX 0 C22 1 0.330808 0.067919 0.470000 11.00000 0.03619 0.03129 = 0.03819 0.01627 0.00793 0.00050 C25 1 0.547543 0.264687 0.670696 11.00000 0.03847 0.04348 = 0.02747 0.01792 0.01043 0.00617 C8 1 0.875360 0.499444 0.270647 11.00000 0.02844 0.04754 = 0.03298 0.01632 0.01654 0.00530 AFIX 23 H8A 2 0.872787 0.466890 0.183916 11.00000 -1.20000 H8B 2 0.954176 0.475656 0.325601 11.00000 -1.20000 AFIX 0 C3 1 1.103387 0.828193 0.723180 11.00000 0.04506 0.03097 = 0.03571 0.00850 0.01640 0.00029 C7 1 0.903654 0.647070 0.313237 11.00000 0.03889 0.04700 = 0.03368 0.01901 0.01506 -0.00351 AFIX 23 H7A 2 0.970949 0.680165 0.279023 11.00000 -1.20000 H7B 2 0.814388 0.670269 0.276882 11.00000 -1.20000 AFIX 0 C23 1 0.333329 0.091850 0.592933 11.00000 0.04546 0.04941 = 0.04806 0.02931 0.02202 0.00262 AFIX 43 H23 2 0.262195 0.042987 0.608203 11.00000 -1.20000 AFIX 0 C12 1 0.623847 0.396844 0.048068 11.00000 0.04001 0.06116 = 0.02882 0.01712 0.01596 0.00373 AFIX 137 H12A 2 0.660641 0.485209 0.055088 11.00000 -1.50000 H12B 2 0.529433 0.362467 -0.017850 11.00000 -1.50000 H12C 2 0.686474 0.344264 0.026762 11.00000 -1.50000 AFIX 0 C24 1 0.442286 0.188702 0.691954 11.00000 0.05448 0.05699 = 0.03222 0.02421 0.02067 0.00573 AFIX 43 H24 2 0.445861 0.203906 0.775191 11.00000 -1.20000 AFIX 0 C2 1 1.293949 0.939691 0.925005 11.00000 0.04015 0.05136 = 0.04564 0.00233 0.01081 -0.01111 AFIX 23 H2A 2 1.308505 1.021747 0.908894 11.00000 -1.20000 H2B 2 1.360161 0.891796 0.901199 11.00000 -1.20000 AFIX 0 C15 1 0.096513 0.226848 0.020292 11.00000 0.02689 0.07844 = 0.03864 0.02122 0.00366 -0.00159 AFIX 23 H15A 2 0.035474 0.168804 0.042689 11.00000 -1.20000 H15B 2 0.099554 0.178464 -0.061296 11.00000 -1.20000 AFIX 0 C1 1 1.318461 0.964434 1.063404 11.00000 0.05232 0.05979 = 0.04497 0.00450 0.00595 -0.00372 AFIX 137 H1A 2 1.303069 0.882470 1.077813 11.00000 -1.50000 H1B 2 1.252628 1.012247 1.085705 11.00000 -1.50000 H1C 2 1.415401 1.014445 1.115414 11.00000 -1.50000 AFIX 0 C16 1 0.035727 0.340464 0.008740 11.00000 0.04625 0.11222 = 0.06245 0.03090 0.01833 0.03241 AFIX 137 H16A 2 -0.062511 0.309831 -0.050302 11.00000 -1.50000 H16B 2 0.090517 0.392967 -0.022084 11.00000 -1.50000 H16C 2 0.039865 0.392070 0.091137 11.00000 -1.50000 AFIX 0 HKLF 4 REM 1_a.res in P-1 REM R1 = 0.0293 for 3760 Fo > 4sig(Fo) and 0.0378 for all 4470 data REM 302 parameters refined using 0 restraints END WGHT 0.0436 0.2798 REM Instructions for potential hydrogen bonds HTAB O5 O4 HTAB N2 O2 HTAB C7 Br1_$1 HTAB C23 O2_$2 HTAB C12 O3_$3 HTAB C12 O3 HTAB C15 O1_$4 REM Highest difference peak 0.222, deepest hole -0.351, 1-sigma level 0.051 Q1 1 0.6739 0.4060 0.4017 11.00000 0.05 0.22 Q2 1 0.6351 0.3429 0.4512 11.00000 0.05 0.21 Q3 1 0.1570 -0.1437 0.2657 11.00000 0.05 0.19 Q4 1 1.1267 0.9095 0.6762 11.00000 0.05 0.18 Q5 1 0.5034 0.3261 0.2359 11.00000 0.05 0.18 Q6 1 0.9988 0.6456 0.2917 11.00000 0.05 0.17 Q7 1 0.5662 0.2943 0.5270 11.00000 0.05 0.17 Q8 1 0.8485 0.6846 0.2582 11.00000 0.05 0.17 Q9 1 0.1452 -0.0164 0.2780 11.00000 0.05 0.17 Q10 1 1.3866 1.0705 1.1196 11.00000 0.05 0.17 Q11 1 0.9352 0.6723 0.3840 11.00000 0.05 0.17 Q12 1 0.8637 0.5786 0.2804 11.00000 0.05 0.16 Q13 1 0.8054 0.4669 0.2716 11.00000 0.05 0.16 Q14 1 0.5668 0.3144 0.3446 11.00000 0.05 0.16 Q15 1 0.4929 0.1993 0.5036 11.00000 0.05 0.16 Q16 1 0.5449 0.2618 0.5966 11.00000 0.05 0.15 Q17 1 0.1839 0.0642 0.5740 11.00000 0.05 0.15 Q18 1 0.6843 0.4630 0.2317 11.00000 0.05 0.15 Q19 1 0.8223 0.6532 0.5002 11.00000 0.05 0.15 Q20 1 0.5597 0.3005 -0.0160 11.00000 0.05 0.14 ; _shelx_res_checksum 31450 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 0.18263(3) -0.06747(2) 0.33334(2) 0.05923(10) Uani 1 1 d . . . . . O002 O 0.24051(13) 0.27105(15) 0.11791(12) 0.0448(3) Uani 1 1 d . . . . . O4 O 0.76183(14) 0.39839(15) 0.61640(12) 0.0448(3) Uani 1 1 d . . . . . O1 O 1.14763(15) 0.86397(15) 0.85252(13) 0.0496(4) Uani 1 1 d . . . . . O2 O 1.18423(16) 0.86031(15) 0.67258(14) 0.0521(4) Uani 1 1 d . . . . . O3 O 0.32343(15) 0.29716(17) -0.02995(12) 0.0541(4) Uani 1 1 d . . . . . N1 N 0.73979(15) 0.43608(14) 0.27438(13) 0.0280(3) Uani 1 1 d . . . . . O5 O 0.65161(16) 0.35656(16) 0.77351(12) 0.0528(4) Uani 1 1 d . . . . . H5 H 0.7148 0.3870 0.7520 0.079 Uiso 1 1 calc R U . . . N2 N 0.96086(18) 0.71090(16) 0.45082(15) 0.0425(4) Uani 1 1 d . . . . . H2 H 1.0437 0.7657 0.4845 0.051 Uiso 1 1 calc R U . . . C17 C 0.49678(18) 0.32597(16) 0.30288(15) 0.0279(3) Uani 1 1 d . . . . . H17 H 0.4136 0.2847 0.3087 0.034 Uiso 1 1 calc R U . . . C21 C 0.43386(19) 0.14113(17) 0.44561(16) 0.0316(4) Uani 1 1 d . . . . . H21 H 0.4321 0.1211 0.3625 0.038 Uiso 1 1 calc R U . . . C11 C 0.61604(18) 0.39465(16) 0.17311(15) 0.0279(3) Uani 1 1 d . . . . . C9 C 0.74662(17) 0.45633(16) 0.40615(15) 0.0261(3) Uani 1 1 d . . . . . H9 H 0.8357 0.4380 0.4543 0.031 Uiso 1 1 calc R U . . . C18 C 0.62145(17) 0.36383(16) 0.40561(15) 0.0270(3) Uani 1 1 d . . . . . C14 C 0.34796(19) 0.30478(17) 0.08000(16) 0.0328(4) Uani 1 1 d . . . . . C5 C 0.89570(19) 0.69200(17) 0.53054(17) 0.0321(4) Uani 1 1 d . . . . . C13 C 0.48791(17) 0.34690(16) 0.18599(15) 0.0275(3) Uani 1 1 d . . . . . C20 C 0.54102(18) 0.24518(17) 0.54445(16) 0.0296(4) Uani 1 1 d . . . . . C19 C 0.64614(18) 0.33639(17) 0.52423(15) 0.0304(4) Uani 1 1 d . . . . . C10 C 0.74940(18) 0.59967(17) 0.47274(17) 0.0315(4) Uani 1 1 d . . . . . H10A H 0.6859 0.6296 0.4106 0.038 Uiso 1 1 calc R U . . . H10B H 0.7117 0.6027 0.5397 0.038 Uiso 1 1 calc R U . . . C4 C 0.9596(2) 0.74888(18) 0.65993(17) 0.0365(4) Uani 1 1 d . . . . . H4 H 0.9070 0.7355 0.7096 0.044 Uiso 1 1 calc R U . . . C22 C 0.3308(2) 0.06792(18) 0.47000(18) 0.0366(4) Uani 1 1 d . . . . . C25 C 0.5475(2) 0.26469(19) 0.67070(17) 0.0361(4) Uani 1 1 d . . . . . C8 C 0.87536(19) 0.49944(19) 0.27065(17) 0.0349(4) Uani 1 1 d . . . . . H8A H 0.8728 0.4669 0.1839 0.042 Uiso 1 1 calc R U . . . H8B H 0.9542 0.4757 0.3256 0.042 Uiso 1 1 calc R U . . . C3 C 1.1034(2) 0.82819(18) 0.72318(18) 0.0385(4) Uani 1 1 d . . . . . C7 C 0.9037(2) 0.64707(19) 0.31324(17) 0.0398(4) Uani 1 1 d . . . . . H7A H 0.9709 0.6802 0.2790 0.048 Uiso 1 1 calc R U . . . H7B H 0.8144 0.6703 0.2769 0.048 Uiso 1 1 calc R U . . . C23 C 0.3333(2) 0.0919(2) 0.5929(2) 0.0447(5) Uani 1 1 d . . . . . H23 H 0.2622 0.0430 0.6082 0.054 Uiso 1 1 calc R U . . . C12 C 0.6238(2) 0.3968(2) 0.04807(17) 0.0431(5) Uani 1 1 d . . . . . H12A H 0.6606 0.4852 0.0551 0.065 Uiso 1 1 calc R U . . . H12B H 0.5294 0.3625 -0.0178 0.065 Uiso 1 1 calc R U . . . H12C H 0.6865 0.3443 0.0268 0.065 Uiso 1 1 calc R U . . . C24 C 0.4423(2) 0.1887(2) 0.69195(19) 0.0456(5) Uani 1 1 d . . . . . H24 H 0.4459 0.2039 0.7752 0.055 Uiso 1 1 calc R U . . . C2 C 1.2939(2) 0.9397(2) 0.9250(2) 0.0526(5) Uani 1 1 d . . . . . H2A H 1.3085 1.0217 0.9089 0.063 Uiso 1 1 calc R U . . . H2B H 1.3602 0.8918 0.9012 0.063 Uiso 1 1 calc R U . . . C15 C 0.0965(2) 0.2268(2) 0.0203(2) 0.0515(5) Uani 1 1 d . . . . . H15A H 0.0355 0.1688 0.0427 0.062 Uiso 1 1 calc R U . . . H15B H 0.0996 0.1785 -0.0613 0.062 Uiso 1 1 calc R U . . . C1 C 1.3185(3) 0.9644(2) 1.0634(2) 0.0604(6) Uani 1 1 d . . . . . H1A H 1.3031 0.8825 1.0778 0.091 Uiso 1 1 calc R U . . . H1B H 1.2526 1.0122 1.0857 0.091 Uiso 1 1 calc R U . . . H1C H 1.4154 1.0144 1.1154 0.091 Uiso 1 1 calc R U . . . C16 C 0.0357(3) 0.3405(3) 0.0087(3) 0.0725(8) Uani 1 1 d . . . . . H16A H -0.0625 0.3098 -0.0503 0.109 Uiso 1 1 calc R U . . . H16B H 0.0905 0.3930 -0.0221 0.109 Uiso 1 1 calc R U . . . H16C H 0.0399 0.3921 0.0911 0.109 Uiso 1 1 calc R U . . . 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 0.05496(15) 0.04497(14) 0.05611(16) 0.01402(11) 0.00730(11) -0.01557(10) O002 0.0255(6) 0.0727(10) 0.0318(7) 0.0234(7) 0.0053(5) 0.0006(6) O4 0.0319(7) 0.0635(9) 0.0287(7) 0.0206(6) 0.0021(5) -0.0074(6) O1 0.0420(8) 0.0563(9) 0.0334(7) 0.0038(6) 0.0120(6) -0.0118(7) O2 0.0503(9) 0.0538(9) 0.0447(8) 0.0148(7) 0.0198(7) -0.0114(7) O3 0.0416(8) 0.0838(11) 0.0268(7) 0.0225(7) 0.0052(6) -0.0051(7) N1 0.0262(7) 0.0334(8) 0.0262(7) 0.0114(6) 0.0126(6) 0.0034(6) O5 0.0526(9) 0.0675(10) 0.0231(6) 0.0124(6) 0.0079(6) -0.0112(7) N2 0.0408(9) 0.0458(9) 0.0337(8) 0.0122(7) 0.0146(7) -0.0100(7) C17 0.0261(8) 0.0310(9) 0.0270(8) 0.0121(7) 0.0105(7) 0.0023(7) C21 0.0352(9) 0.0324(9) 0.0277(9) 0.0144(7) 0.0100(7) 0.0054(7) C11 0.0327(9) 0.0272(8) 0.0255(8) 0.0097(7) 0.0129(7) 0.0067(7) C9 0.0231(8) 0.0322(9) 0.0232(8) 0.0118(7) 0.0083(6) 0.0037(7) C18 0.0258(8) 0.0313(9) 0.0241(8) 0.0111(7) 0.0098(7) 0.0030(7) C14 0.0326(9) 0.0352(9) 0.0277(9) 0.0130(7) 0.0085(7) 0.0020(7) C5 0.0345(9) 0.0276(9) 0.0361(9) 0.0124(7) 0.0152(8) 0.0053(7) C13 0.0278(8) 0.0303(9) 0.0227(8) 0.0104(7) 0.0075(7) 0.0032(7) C20 0.0285(8) 0.0365(9) 0.0262(8) 0.0166(7) 0.0091(7) 0.0067(7) C19 0.0254(8) 0.0384(9) 0.0249(8) 0.0127(7) 0.0068(7) 0.0031(7) C10 0.0301(9) 0.0357(9) 0.0301(9) 0.0112(7) 0.0139(7) 0.0057(7) C4 0.0403(10) 0.0339(9) 0.0337(9) 0.0082(8) 0.0182(8) 0.0007(8) C22 0.0362(10) 0.0313(9) 0.0382(10) 0.0163(8) 0.0079(8) 0.0005(8) C25 0.0385(10) 0.0435(10) 0.0275(9) 0.0179(8) 0.0104(8) 0.0062(8) C8 0.0284(9) 0.0475(11) 0.0330(9) 0.0163(8) 0.0165(7) 0.0053(8) C3 0.0451(11) 0.0310(9) 0.0357(10) 0.0085(8) 0.0164(9) 0.0003(8) C7 0.0389(10) 0.0470(11) 0.0337(10) 0.0190(8) 0.0151(8) -0.0035(8) C23 0.0455(11) 0.0494(12) 0.0481(12) 0.0293(10) 0.0220(9) 0.0026(9) C12 0.0400(10) 0.0612(13) 0.0288(9) 0.0171(9) 0.0160(8) 0.0037(9) C24 0.0545(12) 0.0570(13) 0.0322(10) 0.0242(9) 0.0207(9) 0.0057(10) C2 0.0402(11) 0.0514(13) 0.0456(12) 0.0023(10) 0.0108(9) -0.0111(9) C15 0.0269(10) 0.0784(16) 0.0386(11) 0.0212(11) 0.0037(8) -0.0016(10) C1 0.0523(13) 0.0598(14) 0.0450(13) 0.0045(11) 0.0059(10) -0.0037(11) C16 0.0462(14) 0.112(2) 0.0625(16) 0.0309(16) 0.0183(12) 0.0324(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' Br Br -0.2901 2.4595 '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' 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 C14 O002 C15 116.33(14) . . ? C3 O1 C2 116.44(15) . . ? C11 N1 C8 122.57(14) . . ? C11 N1 C9 122.81(13) . . ? C8 N1 C9 112.57(13) . . ? C25 O5 H5 109.5 . . ? C5 N2 C7 125.66(16) . . ? C5 N2 H2 117.2 . . ? C7 N2 H2 117.2 . . ? C18 C17 C13 122.44(15) . . ? C18 C17 H17 118.8 . . ? C13 C17 H17 118.8 . . ? C22 C21 C20 120.65(16) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? N1 C11 C13 119.90(14) . . ? N1 C11 C12 116.91(15) . . ? C13 C11 C12 123.13(16) . . ? N1 C9 C18 110.49(13) . . ? N1 C9 C10 110.49(13) . . ? C18 C9 C10 110.65(13) . . ? N1 C9 H9 108.4 . . ? C18 C9 H9 108.4 . . ? C10 C9 H9 108.4 . . ? C17 C18 C19 127.15(15) . . ? C17 C18 C9 118.00(14) . . ? C19 C18 C9 114.52(14) . . ? O3 C14 O002 120.66(16) . . ? O3 C14 C13 127.83(16) . . ? O002 C14 C13 111.51(14) . . ? N2 C5 C4 122.62(17) . . ? N2 C5 C10 117.76(16) . . ? C4 C5 C10 119.57(16) . . ? C11 C13 C17 118.17(15) . . ? C11 C13 C14 122.59(14) . . ? C17 C13 C14 118.90(15) . . ? C21 C20 C25 117.74(16) . . ? C21 C20 C19 123.86(14) . . ? C25 C20 C19 118.39(15) . . ? O4 C19 C18 117.39(15) . . ? O4 C19 C20 118.39(14) . . ? C18 C19 C20 124.16(14) . . ? C5 C10 C9 114.30(14) . . ? C5 C10 H10A 108.7 . . ? C9 C10 H10A 108.7 . . ? C5 C10 H10B 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C5 C4 C3 123.11(17) . . ? C5 C4 H4 118.4 . . ? C3 C4 H4 118.4 . . ? C21 C22 C23 121.20(17) . . ? C21 C22 Br1 119.68(14) . . ? C23 C22 Br1 119.12(14) . . ? O5 C25 C24 117.49(16) . . ? O5 C25 C20 122.62(16) . . ? C24 C25 C20 119.88(17) . . ? N1 C8 C7 113.02(14) . . ? N1 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? N1 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? O2 C3 O1 120.94(18) . . ? O2 C3 C4 126.77(18) . . ? O1 C3 C4 112.26(16) . . ? N2 C7 C8 114.19(15) . . ? N2 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? N2 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C24 C23 C22 118.90(17) . . ? C24 C23 H23 120.5 . . ? C22 C23 H23 120.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C23 C24 C25 121.38(17) . . ? C23 C24 H24 119.3 . . ? C25 C24 H24 119.3 . . ? O1 C2 C1 106.69(17) . . ? O1 C2 H2A 110.4 . . ? C1 C2 H2A 110.4 . . ? O1 C2 H2B 110.4 . . ? C1 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? O002 C15 C16 110.2(2) . . ? O002 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? O002 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 C22 1.8885(19) . ? O002 C14 1.343(2) . ? O002 C15 1.451(2) . ? O4 C19 1.253(2) . ? O1 C3 1.356(2) . ? O1 C2 1.441(2) . ? O2 C3 1.220(2) . ? O3 C14 1.206(2) . ? N1 C11 1.335(2) . ? N1 C8 1.469(2) . ? N1 C9 1.474(2) . ? O5 C25 1.344(2) . ? O5 H5 0.8200 . ? N2 C5 1.345(2) . ? N2 C7 1.447(2) . ? N2 H2 0.8600 . ? C17 C18 1.351(2) . ? C17 C13 1.425(2) . ? C17 H17 0.9300 . ? C21 C22 1.377(2) . ? C21 C20 1.397(2) . ? C21 H21 0.9300 . ? C11 C13 1.400(2) . ? C11 C12 1.497(2) . ? C9 C18 1.506(2) . ? C9 C10 1.545(2) . ? C9 H9 0.9800 . ? C18 C19 1.452(2) . ? C14 C13 1.464(2) . ? C5 C4 1.359(3) . ? C5 C10 1.499(2) . ? C20 C25 1.412(2) . ? C20 C19 1.478(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C4 C3 1.426(3) . ? C4 H4 0.9300 . ? C22 C23 1.381(3) . ? C25 C24 1.388(3) . ? C8 C7 1.514(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C23 C24 1.369(3) . ? C23 H23 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C24 H24 0.9300 . ? C2 C1 1.498(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C15 C16 1.484(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 O5 H5 O4 0.82 1.83 2.5422(18) 145.1 . N2 H2 O2 0.86 2.07 2.727(2) 132.6 . C7 H7A Br1 0.97 3.03 3.8145(18) 138.9 1_665 C23 H23 O2 0.93 2.44 3.274(2) 148.8 1_445 C12 H12A O3 0.96 2.47 3.400(3) 162.1 2_665 C12 H12B O3 0.96 2.06 2.836(2) 137.2 . C15 H15A O1 0.97 2.56 3.434(3) 149.2 2_666 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 C8 N1 C11 C13 -173.65(16) . . . . ? C9 N1 C11 C13 -11.1(2) . . . . ? C8 N1 C11 C12 8.9(2) . . . . ? C9 N1 C11 C12 171.45(16) . . . . ? C11 N1 C9 C18 30.0(2) . . . . ? C8 N1 C9 C18 -165.90(14) . . . . ? C11 N1 C9 C10 -92.78(18) . . . . ? C8 N1 C9 C10 71.32(17) . . . . ? C13 C17 C18 C19 -173.41(16) . . . . ? C13 C17 C18 C9 13.6(2) . . . . ? N1 C9 C18 C17 -30.3(2) . . . . ? C10 C9 C18 C17 92.42(18) . . . . ? N1 C9 C18 C19 155.85(14) . . . . ? C10 C9 C18 C19 -81.46(18) . . . . ? C15 O002 C14 O3 -0.4(3) . . . . ? C15 O002 C14 C13 -179.66(17) . . . . ? C7 N2 C5 C4 175.64(18) . . . . ? C7 N2 C5 C10 -1.7(3) . . . . ? N1 C11 C13 C17 -9.2(2) . . . . ? C12 C11 C13 C17 168.07(16) . . . . ? N1 C11 C13 C14 177.56(16) . . . . ? C12 C11 C13 C14 -5.2(3) . . . . ? C18 C17 C13 C11 7.5(3) . . . . ? C18 C17 C13 C14 -178.97(16) . . . . ? O3 C14 C13 C11 4.8(3) . . . . ? O002 C14 C13 C11 -175.97(16) . . . . ? O3 C14 C13 C17 -168.37(19) . . . . ? O002 C14 C13 C17 10.8(2) . . . . ? C22 C21 C20 C25 5.6(3) . . . . ? C22 C21 C20 C19 -173.56(17) . . . . ? C17 C18 C19 O4 -167.98(18) . . . . ? C9 C18 C19 O4 5.2(2) . . . . ? C17 C18 C19 C20 9.0(3) . . . . ? C9 C18 C19 C20 -177.76(15) . . . . ? C21 C20 C19 O4 -158.05(17) . . . . ? C25 C20 C19 O4 22.7(2) . . . . ? C21 C20 C19 C18 25.0(3) . . . . ? C25 C20 C19 C18 -154.23(17) . . . . ? N2 C5 C10 C9 64.3(2) . . . . ? C4 C5 C10 C9 -113.07(18) . . . . ? N1 C9 C10 C5 -83.48(17) . . . . ? C18 C9 C10 C5 153.83(14) . . . . ? N2 C5 C4 C3 -3.2(3) . . . . ? C10 C5 C4 C3 174.07(17) . . . . ? C20 C21 C22 C23 -2.4(3) . . . . ? C20 C21 C22 Br1 177.37(13) . . . . ? C21 C20 C25 O5 175.74(17) . . . . ? C19 C20 C25 O5 -5.0(3) . . . . ? C21 C20 C25 C24 -5.4(3) . . . . ? C19 C20 C25 C24 173.91(17) . . . . ? C11 N1 C8 C7 92.42(19) . . . . ? C9 N1 C8 C7 -71.71(18) . . . . ? C2 O1 C3 O2 -0.7(3) . . . . ? C2 O1 C3 C4 177.38(17) . . . . ? C5 C4 C3 O2 3.6(3) . . . . ? C5 C4 C3 O1 -174.29(17) . . . . ? C5 N2 C7 C8 -60.1(3) . . . . ? N1 C8 C7 N2 79.9(2) . . . . ? C21 C22 C23 C24 -1.3(3) . . . . ? Br1 C22 C23 C24 178.95(16) . . . . ? C22 C23 C24 C25 1.5(3) . . . . ? O5 C25 C24 C23 -179.2(2) . . . . ? C20 C25 C24 C23 1.8(3) . . . . ? C3 O1 C2 C1 -178.73(18) . . . . ? C14 O002 C15 C16 -85.8(2) . . . . ?