#------------------------------------------------------------------------------ #$Date: 2021-07-05 21:06:38 +0300 (Mon, 05 Jul 2021) $ #$Revision: 267225 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060690.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_7060690 loop_ _publ_author_name 'Yadav, Rahul' 'Parvin, Tasneem' _publ_section_title ; Multicomponent synthesis of styryl linked benzo[h]pyrazolo[3,4-b]quinoline-5,6(10H)-diones by liquid assisted grinding ; _journal_issue 23 _journal_name_full 'New Journal of Chemistry' _journal_page_first 10388 _journal_page_last 10395 _journal_paper_doi 10.1039/D1NJ00770J _journal_volume 45 _journal_year 2021 _chemical_formula_moiety 'C29 H18 Br N3 O2' _chemical_formula_sum 'C29 H18 Br N3 O2' _chemical_formula_weight 520.37 _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 ; 2020-02-05 deposited with the CCDC. 2021-05-03 downloaded from the CCDC. ; _cell_angle_alpha 110.376(2) _cell_angle_beta 102.926(2) _cell_angle_gamma 108.235(2) _cell_formula_units_Z 2 _cell_length_a 10.6575(7) _cell_length_b 10.8837(7) _cell_length_c 11.6850(8) _cell_measurement_reflns_used 3797 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 25.996 _cell_measurement_theta_min 2.959 _cell_volume 1119.38(13) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014 (Sheldrick 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0774 _diffrn_reflns_av_unetI/netI 0.1223 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 14398 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.996 _diffrn_reflns_theta_min 2.959 _exptl_absorpt_coefficient_mu 1.870 _exptl_absorpt_correction_T_max 0.571 _exptl_absorpt_correction_T_min 0.565 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS-2016/2 _exptl_crystal_colour ORANGE _exptl_crystal_density_diffrn 1.544 _exptl_crystal_description BLOCK _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.300 _refine_diff_density_max 0.270 _refine_diff_density_min -0.390 _refine_diff_density_rms 0.066 _refine_ls_extinction_coef 0.0024(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 318 _refine_ls_number_reflns 4391 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.010 _refine_ls_R_factor_all 0.1500 _refine_ls_R_factor_gt 0.0570 _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^)+(0.0211P)^2^+0.6426P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0735 _refine_ls_wR_factor_ref 0.0932 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2306 _reflns_number_total 4391 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj00770j2.cif _cod_data_source_block PP_a _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas Adding full bibliography for 7060689--7060690.cif. ; _cod_database_code 7060690 _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_min 0.604 _shelx_estimated_absorpt_t_max 0.604 _shelx_res_file ; PP_a.res created by SHELXL-2014/7 TITL PP_a.res in P-1 CELL 0.71073 10.6575 10.8837 11.6850 110.376 102.926 108.235 ZERR 2.000 0.0007 0.0007 0.0008 0.002 0.002 0.002 LATT 1 SFAC C H Br N O UNIT 58 36 2 6 4 OMIT -7 8 9 OMIT -2 1 5 OMIT -3 52 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 CONF SIZE 0.3 0.3 0.3 TEMP 25 WGHT 0.021100 0.642600 EXTI 0.002433 FVAR 0.47794 BR1 3 1.049711 -0.168264 0.249677 11.00000 0.06502 0.06656 = 0.07280 0.03034 0.03488 0.04851 C1 1 0.829789 0.083898 0.257823 11.00000 0.04906 0.04002 = 0.05884 0.02686 0.02773 0.02508 AFIX 43 H1 2 0.823160 0.148081 0.223651 11.00000 -1.20000 AFIX 0 C2 1 0.914573 0.013373 0.228580 11.00000 0.04776 0.04558 = 0.05433 0.02610 0.02929 0.02259 AFIX 43 H2 2 0.962657 0.028277 0.173842 11.00000 -1.20000 AFIX 0 C3 1 0.926833 -0.078658 0.281223 11.00000 0.03380 0.04059 = 0.04536 0.01507 0.01440 0.02082 C4 1 0.852351 -0.104600 0.358510 11.00000 0.05304 0.04450 = 0.05055 0.02708 0.02129 0.03097 AFIX 43 H3 2 0.860026 -0.168371 0.392897 11.00000 -1.20000 AFIX 0 C5 1 0.766591 -0.036055 0.384770 11.00000 0.04609 0.05211 = 0.04637 0.02844 0.02495 0.02872 AFIX 43 H4 2 0.715171 -0.055150 0.436050 11.00000 -1.20000 AFIX 0 C6 1 0.754953 0.061564 0.336194 11.00000 0.03341 0.03128 = 0.03484 0.01137 0.01235 0.01786 C7 1 0.666260 0.138422 0.364715 11.00000 0.04360 0.03747 = 0.04700 0.02236 0.01667 0.02471 AFIX 43 H5 2 0.661335 0.198454 0.325115 11.00000 -1.20000 AFIX 0 C8 1 0.593029 0.130915 0.440673 11.00000 0.03930 0.04109 = 0.04808 0.02346 0.01807 0.02531 AFIX 43 H6 2 0.594362 0.069009 0.478804 11.00000 -1.20000 AFIX 0 C9 1 0.509154 0.213958 0.469308 11.00000 0.03181 0.03654 = 0.04000 0.02253 0.01561 0.01782 C10 1 0.532422 0.307377 0.598718 11.00000 0.02673 0.03858 = 0.03942 0.02324 0.01121 0.01642 C11 1 0.632217 0.314766 0.714344 11.00000 0.04466 0.05805 = 0.05020 0.03585 0.01971 0.03353 C12 1 0.669653 0.432846 0.851600 11.00000 0.03261 0.06635 = 0.04316 0.03611 0.01255 0.02211 C13 1 0.593993 0.524850 0.865436 11.00000 0.03403 0.04576 = 0.03237 0.02317 0.00861 0.01356 C14 1 0.624136 0.631120 0.988931 11.00000 0.04329 0.05343 = 0.03337 0.01949 0.00316 0.01001 AFIX 43 H7 2 0.697021 0.647363 1.061236 11.00000 -1.20000 AFIX 0 C15 1 0.548596 0.712367 1.006204 11.00000 0.05836 0.03849 = 0.03987 0.00691 0.01625 0.01056 AFIX 43 H8 2 0.571397 0.785185 1.089092 11.00000 -1.20000 AFIX 0 C16 1 0.437799 0.685064 0.898970 11.00000 0.04870 0.05214 = 0.04669 0.01534 0.01804 0.02447 AFIX 43 H9 2 0.382749 0.736525 0.910723 11.00000 -1.20000 AFIX 0 C17 1 0.408203 0.582317 0.774863 11.00000 0.04076 0.05150 = 0.03629 0.01915 0.01393 0.02543 AFIX 43 H10 2 0.334750 0.566707 0.703371 11.00000 -1.20000 AFIX 0 C18 1 0.486931 0.501747 0.755354 11.00000 0.02972 0.03600 = 0.03205 0.01685 0.00969 0.01340 C19 1 0.458608 0.396389 0.621100 11.00000 0.02157 0.03787 = 0.03246 0.01969 0.00768 0.01292 C20 1 0.338264 0.300898 0.403141 11.00000 0.02887 0.03992 = 0.03211 0.02229 0.01190 0.01794 C21 1 0.405068 0.208611 0.367710 11.00000 0.02630 0.03152 = 0.03323 0.01290 0.01058 0.01462 C22 1 0.336529 0.126921 0.228389 11.00000 0.03360 0.03599 = 0.03909 0.01410 0.01298 0.01522 C23 1 0.351284 0.002315 0.133422 11.00000 0.05578 0.04745 = 0.04218 0.01186 0.01287 0.02826 AFIX 137 H11 2 0.342439 -0.069909 0.164188 11.00000 -1.50000 H12 2 0.442895 0.036511 0.127062 11.00000 -1.50000 H13 2 0.277943 -0.039249 0.048357 11.00000 -1.50000 AFIX 0 C24 1 0.146918 0.339406 0.265863 11.00000 0.02449 0.04080 = 0.03917 0.02240 0.00770 0.01773 C25 1 0.135152 0.440743 0.368010 11.00000 0.05802 0.06583 = 0.03530 0.01141 0.00058 0.04263 AFIX 43 H14 2 0.189344 0.468684 0.454641 11.00000 -1.20000 AFIX 0 C26 1 0.042394 0.500819 0.341244 11.00000 0.05797 0.06507 = 0.04973 0.01148 0.00576 0.04129 AFIX 43 H15 2 0.034807 0.569668 0.410276 11.00000 -1.20000 AFIX 0 C27 1 -0.038300 0.459992 0.214261 11.00000 0.03333 0.05039 = 0.06268 0.02924 0.00296 0.02160 AFIX 43 H16 2 -0.101243 0.500037 0.196871 11.00000 -1.20000 AFIX 0 C28 1 -0.025775 0.360162 0.113375 11.00000 0.04288 0.06124 = 0.04108 0.02869 0.00390 0.02243 AFIX 43 H17 2 -0.079966 0.332940 0.026946 11.00000 -1.20000 AFIX 0 C29 1 0.066242 0.298978 0.137808 11.00000 0.05021 0.05576 = 0.04016 0.02616 0.01291 0.03107 AFIX 43 H18 2 0.073830 0.230788 0.068248 11.00000 -1.20000 AFIX 0 N1 4 0.361996 0.394013 0.523983 11.00000 0.02940 0.04022 = 0.03207 0.01715 0.00842 0.01971 N2 4 0.241350 0.275301 0.288952 11.00000 0.03176 0.04206 = 0.03065 0.01467 0.00818 0.02027 N3 4 0.240251 0.166520 0.182553 11.00000 0.03605 0.04474 = 0.03548 0.01582 0.00979 0.02064 O1 5 0.682033 0.227688 0.706993 11.00000 0.10053 0.10403 = 0.06357 0.04193 0.01961 0.08219 O2 5 0.756187 0.440182 0.943259 11.00000 0.06755 0.09858 = 0.05402 0.04166 0.00336 0.04692 HKLF 4 REM PP_a.res in P-1 REM R1 = 0.0570 for 2306 Fo > 4sig(Fo) and 0.1500 for all 4391 data REM 318 parameters refined using 0 restraints END WGHT 0.0240 0.5304 REM Highest difference peak 0.270, deepest hole -0.390, 1-sigma level 0.066 Q1 1 0.3304 0.0430 0.3239 11.00000 0.05 0.27 Q2 1 0.1239 0.6007 0.2959 11.00000 0.05 0.25 Q3 1 0.3968 0.1635 0.3977 11.00000 0.05 0.25 Q4 1 0.3981 0.3010 0.3794 11.00000 0.05 0.25 Q5 1 0.7457 -0.0033 0.2472 11.00000 0.05 0.24 Q6 1 0.2729 -0.0234 0.3038 11.00000 0.05 0.24 Q7 1 0.6674 0.4919 0.8846 11.00000 0.05 0.23 Q8 1 1.0267 -0.3059 0.2270 11.00000 0.05 0.23 Q9 1 0.1612 0.1198 0.2226 11.00000 0.05 0.23 Q10 1 1.0991 -0.0627 0.2089 11.00000 0.05 0.23 Q11 1 0.5553 -0.0371 0.5137 11.00000 0.05 0.23 Q12 1 0.5011 0.0216 0.3218 11.00000 0.05 0.22 Q13 1 0.7124 0.7967 0.9616 11.00000 0.05 0.22 Q14 1 0.8959 0.3543 0.7887 11.00000 0.05 0.22 Q15 1 0.8074 0.1029 0.3184 11.00000 0.05 0.22 Q16 1 0.4796 0.4623 0.8184 11.00000 0.05 0.22 Q17 1 1.0546 -0.0795 0.3877 11.00000 0.05 0.21 Q18 1 0.2093 -0.1959 0.1634 11.00000 0.05 0.21 Q19 1 0.7546 0.0794 0.5463 11.00000 0.05 0.21 Q20 1 0.4955 0.5630 0.7610 11.00000 0.05 0.21 ; _shelx_res_checksum 70142 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 1.04971(5) -0.16826(5) 0.24968(5) 0.0610(2) Uani 1 1 d . . . . . C1 C 0.8298(4) 0.0839(4) 0.2578(4) 0.0447(11) Uani 1 1 d . . . . . H1 H 0.8232 0.1481 0.2237 0.054 Uiso 1 1 calc R U . . . C2 C 0.9146(4) 0.0134(4) 0.2286(4) 0.0454(11) Uani 1 1 d . . . . . H2 H 0.9627 0.0283 0.1738 0.054 Uiso 1 1 calc R U . . . C3 C 0.9268(4) -0.0787(4) 0.2812(4) 0.0400(11) Uani 1 1 d . . . . . C4 C 0.8524(4) -0.1046(4) 0.3585(4) 0.0444(11) Uani 1 1 d . . . . . H3 H 0.8600 -0.1684 0.3929 0.053 Uiso 1 1 calc R U . . . C5 C 0.7666(4) -0.0361(4) 0.3848(4) 0.0426(11) Uani 1 1 d . . . . . H4 H 0.7152 -0.0551 0.4361 0.051 Uiso 1 1 calc R U . . . C6 C 0.7550(4) 0.0616(4) 0.3362(4) 0.0333(10) Uani 1 1 d . . . . . C7 C 0.6663(4) 0.1384(4) 0.3647(4) 0.0396(11) Uani 1 1 d . . . . . H5 H 0.6613 0.1985 0.3251 0.048 Uiso 1 1 calc R U . . . C8 C 0.5930(4) 0.1309(4) 0.4407(4) 0.0392(11) Uani 1 1 d . . . . . H6 H 0.5944 0.0690 0.4788 0.047 Uiso 1 1 calc R U . . . C9 C 0.5092(4) 0.2140(4) 0.4693(4) 0.0331(10) Uani 1 1 d . . . . . C10 C 0.5324(4) 0.3074(4) 0.5987(4) 0.0327(10) Uani 1 1 d . . . . . C11 C 0.6322(4) 0.3148(5) 0.7143(4) 0.0438(11) Uani 1 1 d . . . . . C12 C 0.6697(4) 0.4328(5) 0.8516(4) 0.0438(11) Uani 1 1 d . . . . . C13 C 0.5940(4) 0.5249(4) 0.8654(4) 0.0374(10) Uani 1 1 d . . . . . C14 C 0.6241(4) 0.6311(5) 0.9889(4) 0.0486(12) Uani 1 1 d . . . . . H7 H 0.6970 0.6474 1.0612 0.058 Uiso 1 1 calc R U . . . C15 C 0.5486(5) 0.7124(4) 1.0062(4) 0.0522(12) Uani 1 1 d . . . . . H8 H 0.5714 0.7852 1.0891 0.063 Uiso 1 1 calc R U . . . C16 C 0.4378(5) 0.6851(5) 0.8990(4) 0.0505(12) Uani 1 1 d . . . . . H9 H 0.3827 0.7365 0.9107 0.061 Uiso 1 1 calc R U . . . C17 C 0.4082(4) 0.5823(4) 0.7749(4) 0.0416(11) Uani 1 1 d . . . . . H10 H 0.3347 0.5667 0.7034 0.050 Uiso 1 1 calc R U . . . C18 C 0.4869(4) 0.5017(4) 0.7554(4) 0.0327(10) Uani 1 1 d . . . . . C19 C 0.4586(4) 0.3964(4) 0.6211(4) 0.0298(9) Uani 1 1 d . . . . . C20 C 0.3383(4) 0.3009(4) 0.4031(4) 0.0307(9) Uani 1 1 d . . . . . C21 C 0.4051(4) 0.2086(4) 0.3677(4) 0.0304(9) Uani 1 1 d . . . . . C22 C 0.3365(4) 0.1269(4) 0.2284(4) 0.0372(10) Uani 1 1 d . . . . . C23 C 0.3513(4) 0.0023(4) 0.1334(4) 0.0504(12) Uani 1 1 d . . . . . H11 H 0.3424 -0.0699 0.1642 0.076 Uiso 1 1 calc R U . . . H12 H 0.4429 0.0365 0.1271 0.076 Uiso 1 1 calc R U . . . H13 H 0.2779 -0.0392 0.0484 0.076 Uiso 1 1 calc R U . . . C24 C 0.1469(4) 0.3394(4) 0.2659(4) 0.0332(10) Uani 1 1 d . . . . . C25 C 0.1352(4) 0.4407(5) 0.3680(4) 0.0554(13) Uani 1 1 d . . . . . H14 H 0.1893 0.4687 0.4546 0.067 Uiso 1 1 calc R U . . . C26 C 0.0424(5) 0.5008(5) 0.3412(4) 0.0608(14) Uani 1 1 d . . . . . H15 H 0.0348 0.5697 0.4103 0.073 Uiso 1 1 calc R U . . . C27 C -0.0383(4) 0.4600(5) 0.2143(4) 0.0495(12) Uani 1 1 d . . . . . H16 H -0.1012 0.5000 0.1969 0.059 Uiso 1 1 calc R U . . . C28 C -0.0258(4) 0.3602(5) 0.1134(4) 0.0489(12) Uani 1 1 d . . . . . H17 H -0.0800 0.3329 0.0269 0.059 Uiso 1 1 calc R U . . . C29 C 0.0662(4) 0.2990(4) 0.1378(4) 0.0457(11) Uani 1 1 d . . . . . H18 H 0.0738 0.2308 0.0682 0.055 Uiso 1 1 calc R U . . . N1 N 0.3620(3) 0.3940(3) 0.5240(3) 0.0329(8) Uani 1 1 d . . . . . N2 N 0.2413(3) 0.2753(3) 0.2890(3) 0.0348(8) Uani 1 1 d . . . . . N3 N 0.2403(3) 0.1665(3) 0.1826(3) 0.0392(8) Uani 1 1 d . . . . . O1 O 0.6820(3) 0.2277(4) 0.7070(3) 0.0795(11) Uani 1 1 d . . . . . O2 O 0.7562(3) 0.4402(3) 0.9433(3) 0.0717(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 0.0650(4) 0.0666(4) 0.0728(4) 0.0303(3) 0.0349(3) 0.0485(3) C1 0.049(3) 0.040(3) 0.059(3) 0.027(3) 0.028(3) 0.025(2) C2 0.048(3) 0.046(3) 0.054(3) 0.026(3) 0.029(3) 0.023(3) C3 0.034(3) 0.041(3) 0.045(3) 0.015(2) 0.014(2) 0.021(2) C4 0.053(3) 0.045(3) 0.051(3) 0.027(2) 0.021(3) 0.031(3) C5 0.046(3) 0.052(3) 0.046(3) 0.028(2) 0.025(2) 0.029(3) C6 0.033(2) 0.031(3) 0.035(2) 0.011(2) 0.012(2) 0.018(2) C7 0.044(3) 0.037(3) 0.047(3) 0.022(2) 0.017(2) 0.025(2) C8 0.039(3) 0.041(3) 0.048(3) 0.023(2) 0.018(2) 0.025(2) C9 0.032(2) 0.037(3) 0.040(3) 0.023(2) 0.016(2) 0.018(2) C10 0.027(2) 0.039(3) 0.039(3) 0.023(2) 0.011(2) 0.016(2) C11 0.045(3) 0.058(3) 0.050(3) 0.036(3) 0.020(2) 0.034(3) C12 0.033(3) 0.066(3) 0.043(3) 0.036(3) 0.013(2) 0.022(3) C13 0.034(3) 0.046(3) 0.032(3) 0.023(2) 0.009(2) 0.014(2) C14 0.043(3) 0.053(3) 0.033(3) 0.019(3) 0.003(2) 0.010(3) C15 0.058(3) 0.038(3) 0.040(3) 0.007(2) 0.016(3) 0.011(3) C16 0.049(3) 0.052(3) 0.047(3) 0.015(3) 0.018(3) 0.024(3) C17 0.041(3) 0.052(3) 0.036(3) 0.019(2) 0.014(2) 0.025(2) C18 0.030(2) 0.036(3) 0.032(2) 0.017(2) 0.010(2) 0.013(2) C19 0.022(2) 0.038(3) 0.032(2) 0.020(2) 0.008(2) 0.013(2) C20 0.029(2) 0.040(3) 0.032(3) 0.022(2) 0.012(2) 0.018(2) C21 0.026(2) 0.032(2) 0.033(3) 0.013(2) 0.011(2) 0.015(2) C22 0.034(3) 0.036(3) 0.039(3) 0.014(2) 0.013(2) 0.015(2) C23 0.056(3) 0.047(3) 0.042(3) 0.012(2) 0.013(2) 0.028(3) C24 0.024(2) 0.041(3) 0.039(3) 0.022(2) 0.008(2) 0.018(2) C25 0.058(3) 0.066(3) 0.035(3) 0.011(3) 0.001(2) 0.043(3) C26 0.058(3) 0.065(3) 0.050(3) 0.011(3) 0.006(3) 0.041(3) C27 0.033(3) 0.050(3) 0.063(3) 0.029(3) 0.003(3) 0.022(3) C28 0.043(3) 0.061(3) 0.041(3) 0.029(3) 0.004(2) 0.022(3) C29 0.050(3) 0.056(3) 0.040(3) 0.026(2) 0.013(2) 0.031(3) N1 0.029(2) 0.040(2) 0.032(2) 0.0172(18) 0.0084(17) 0.0197(18) N2 0.032(2) 0.042(2) 0.031(2) 0.0147(19) 0.0082(17) 0.0203(18) N3 0.036(2) 0.045(2) 0.035(2) 0.0158(19) 0.0098(17) 0.0206(19) O1 0.101(3) 0.104(3) 0.064(2) 0.042(2) 0.020(2) 0.082(3) O2 0.068(2) 0.099(3) 0.054(2) 0.042(2) 0.0034(18) 0.047(2) 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 C6 C1 C2 121.7(4) . . ? C6 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C3 C2 C1 119.2(4) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 120.6(4) . . ? C2 C3 Br1 119.7(3) . . ? C4 C3 Br1 119.7(3) . . ? C3 C4 C5 119.7(4) . . ? C3 C4 H3 120.2 . . ? C5 C4 H3 120.2 . . ? C4 C5 C6 121.3(4) . . ? C4 C5 H4 119.4 . . ? C6 C5 H4 119.4 . . ? C1 C6 C5 117.6(3) . . ? C1 C6 C7 120.0(4) . . ? C5 C6 C7 122.5(4) . . ? C8 C7 C6 126.4(4) . . ? C8 C7 H5 116.8 . . ? C6 C7 H5 116.8 . . ? C7 C8 C9 124.2(4) . . ? C7 C8 H6 117.9 . . ? C9 C8 H6 117.9 . . ? C21 C9 C10 116.5(3) . . ? C21 C9 C8 121.2(3) . . ? C10 C9 C8 122.3(3) . . ? C9 C10 C19 120.3(3) . . ? C9 C10 C11 121.5(3) . . ? C19 C10 C11 118.3(3) . . ? O1 C11 C10 123.2(4) . . ? O1 C11 C12 117.5(4) . . ? C10 C11 C12 119.2(3) . . ? O2 C12 C13 123.7(4) . . ? O2 C12 C11 117.7(4) . . ? C13 C12 C11 118.5(3) . . ? C14 C13 C18 120.0(4) . . ? C14 C13 C12 119.8(4) . . ? C18 C13 C12 120.2(4) . . ? C15 C14 C13 121.1(4) . . ? C15 C14 H7 119.4 . . ? C13 C14 H7 119.4 . . ? C14 C15 C16 119.2(4) . . ? C14 C15 H8 120.4 . . ? C16 C15 H8 120.4 . . ? C17 C16 C15 120.6(4) . . ? C17 C16 H9 119.7 . . ? C15 C16 H9 119.7 . . ? C16 C17 C18 120.7(4) . . ? C16 C17 H10 119.6 . . ? C18 C17 H10 119.6 . . ? C17 C18 C13 118.2(3) . . ? C17 C18 C19 120.3(3) . . ? C13 C18 C19 121.4(3) . . ? N1 C19 C10 123.2(3) . . ? N1 C19 C18 115.3(3) . . ? C10 C19 C18 121.6(3) . . ? N1 C20 N2 126.0(3) . . ? N1 C20 C21 127.2(3) . . ? N2 C20 C21 106.8(3) . . ? C9 C21 C20 117.6(3) . . ? C9 C21 C22 137.6(3) . . ? C20 C21 C22 104.7(3) . . ? N3 C22 C21 111.0(3) . . ? N3 C22 C23 118.2(4) . . ? C21 C22 C23 130.7(4) . . ? C22 C23 H11 109.5 . . ? C22 C23 H12 109.5 . . ? H11 C23 H12 109.5 . . ? C22 C23 H13 109.5 . . ? H11 C23 H13 109.5 . . ? H12 C23 H13 109.5 . . ? C25 C24 C29 119.7(3) . . ? C25 C24 N2 121.5(3) . . ? C29 C24 N2 118.8(3) . . ? C24 C25 C26 119.7(4) . . ? C24 C25 H14 120.2 . . ? C26 C25 H14 120.2 . . ? C27 C26 C25 120.6(4) . . ? C27 C26 H15 119.7 . . ? C25 C26 H15 119.7 . . ? C28 C27 C26 119.5(4) . . ? C28 C27 H16 120.3 . . ? C26 C27 H16 120.3 . . ? C27 C28 C29 120.8(4) . . ? C27 C28 H17 119.6 . . ? C29 C28 H17 119.6 . . ? C28 C29 C24 119.7(4) . . ? C28 C29 H18 120.2 . . ? C24 C29 H18 120.2 . . ? C20 N1 C19 115.2(3) . . ? C20 N2 N3 110.3(3) . . ? C20 N2 C24 131.1(3) . . ? N3 N2 C24 118.6(3) . . ? C22 N3 N2 107.1(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 Br1 C3 1.889(4) . ? C1 C6 1.376(5) . ? C1 C2 1.383(5) . ? C1 H1 0.9300 . ? C2 C3 1.369(5) . ? C2 H2 0.9300 . ? C3 C4 1.372(5) . ? C4 C5 1.371(5) . ? C4 H3 0.9300 . ? C5 C6 1.392(5) . ? C5 H4 0.9300 . ? C6 C7 1.465(5) . ? C7 C8 1.313(5) . ? C7 H5 0.9300 . ? C8 C9 1.469(5) . ? C8 H6 0.9300 . ? C9 C21 1.402(5) . ? C9 C10 1.409(5) . ? C10 C19 1.421(4) . ? C10 C11 1.480(5) . ? C11 O1 1.211(4) . ? C11 C12 1.530(5) . ? C12 O2 1.207(4) . ? C12 C13 1.459(5) . ? C13 C14 1.386(5) . ? C13 C18 1.399(5) . ? C14 C15 1.366(5) . ? C14 H7 0.9300 . ? C15 C16 1.383(5) . ? C15 H8 0.9300 . ? C16 C17 1.378(5) . ? C16 H9 0.9300 . ? C17 C18 1.390(4) . ? C17 H10 0.9300 . ? C18 C19 1.478(5) . ? C19 N1 1.337(4) . ? C20 N1 1.330(4) . ? C20 N2 1.367(4) . ? C20 C21 1.406(4) . ? C21 C22 1.424(5) . ? C22 N3 1.310(4) . ? C22 C23 1.503(5) . ? C23 H11 0.9600 . ? C23 H12 0.9600 . ? C23 H13 0.9600 . ? C24 C25 1.376(5) . ? C24 C29 1.379(5) . ? C24 N2 1.422(4) . ? C25 C26 1.382(5) . ? C25 H14 0.9300 . ? C26 C27 1.367(5) . ? C26 H15 0.9300 . ? C27 C28 1.363(5) . ? C27 H16 0.9300 . ? C28 C29 1.379(5) . ? C28 H17 0.9300 . ? C29 H18 0.9300 . ? N2 N3 1.381(4) . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.4(6) . . . . ? C1 C2 C3 C4 2.2(6) . . . . ? C1 C2 C3 Br1 -176.8(3) . . . . ? C2 C3 C4 C5 -1.0(6) . . . . ? Br1 C3 C4 C5 178.0(3) . . . . ? C3 C4 C5 C6 -1.0(6) . . . . ? C2 C1 C6 C5 -0.5(6) . . . . ? C2 C1 C6 C7 -180.0(4) . . . . ? C4 C5 C6 C1 1.7(6) . . . . ? C4 C5 C6 C7 -178.8(4) . . . . ? C1 C6 C7 C8 -177.8(4) . . . . ? C5 C6 C7 C8 2.7(6) . . . . ? C6 C7 C8 C9 178.0(4) . . . . ? C7 C8 C9 C21 54.1(6) . . . . ? C7 C8 C9 C10 -123.2(4) . . . . ? C21 C9 C10 C19 -3.7(5) . . . . ? C8 C9 C10 C19 173.7(3) . . . . ? C21 C9 C10 C11 175.7(3) . . . . ? C8 C9 C10 C11 -7.0(6) . . . . ? C9 C10 C11 O1 -11.9(6) . . . . ? C19 C10 C11 O1 167.5(4) . . . . ? C9 C10 C11 C12 171.3(3) . . . . ? C19 C10 C11 C12 -9.3(5) . . . . ? O1 C11 C12 O2 6.3(6) . . . . ? C10 C11 C12 O2 -176.7(4) . . . . ? O1 C11 C12 C13 -170.5(4) . . . . ? C10 C11 C12 C13 6.4(5) . . . . ? O2 C12 C13 C14 2.3(6) . . . . ? C11 C12 C13 C14 179.0(4) . . . . ? O2 C12 C13 C18 -174.8(4) . . . . ? C11 C12 C13 C18 1.8(5) . . . . ? C18 C13 C14 C15 1.6(6) . . . . ? C12 C13 C14 C15 -175.6(4) . . . . ? C13 C14 C15 C16 1.8(6) . . . . ? C14 C15 C16 C17 -3.3(6) . . . . ? C15 C16 C17 C18 1.5(6) . . . . ? C16 C17 C18 C13 1.8(6) . . . . ? C16 C17 C18 C19 -177.3(4) . . . . ? C14 C13 C18 C17 -3.3(6) . . . . ? C12 C13 C18 C17 173.8(4) . . . . ? C14 C13 C18 C19 175.8(3) . . . . ? C12 C13 C18 C19 -7.1(5) . . . . ? C9 C10 C19 N1 2.1(6) . . . . ? C11 C10 C19 N1 -177.3(3) . . . . ? C9 C10 C19 C18 -176.3(3) . . . . ? C11 C10 C19 C18 4.3(5) . . . . ? C17 C18 C19 N1 4.6(5) . . . . ? C13 C18 C19 N1 -174.5(3) . . . . ? C17 C18 C19 C10 -176.8(4) . . . . ? C13 C18 C19 C10 4.1(5) . . . . ? C10 C9 C21 C20 2.8(5) . . . . ? C8 C9 C21 C20 -174.6(3) . . . . ? C10 C9 C21 C22 -173.5(4) . . . . ? C8 C9 C21 C22 9.2(7) . . . . ? N1 C20 C21 C9 -0.4(6) . . . . ? N2 C20 C21 C9 -179.4(3) . . . . ? N1 C20 C21 C22 177.0(4) . . . . ? N2 C20 C21 C22 -2.0(4) . . . . ? C9 C21 C22 N3 177.8(4) . . . . ? C20 C21 C22 N3 1.2(4) . . . . ? C9 C21 C22 C23 2.3(8) . . . . ? C20 C21 C22 C23 -174.3(4) . . . . ? C29 C24 C25 C26 0.1(6) . . . . ? N2 C24 C25 C26 179.8(4) . . . . ? C24 C25 C26 C27 0.3(7) . . . . ? C25 C26 C27 C28 -0.7(7) . . . . ? C26 C27 C28 C29 0.6(7) . . . . ? C27 C28 C29 C24 -0.1(6) . . . . ? C25 C24 C29 C28 -0.2(6) . . . . ? N2 C24 C29 C28 -179.9(3) . . . . ? N2 C20 N1 C19 177.6(3) . . . . ? C21 C20 N1 C19 -1.3(6) . . . . ? C10 C19 N1 C20 0.4(5) . . . . ? C18 C19 N1 C20 179.0(3) . . . . ? N1 C20 N2 N3 -176.9(3) . . . . ? C21 C20 N2 N3 2.2(4) . . . . ? N1 C20 N2 C24 2.4(6) . . . . ? C21 C20 N2 C24 -178.5(3) . . . . ? C25 C24 N2 C20 -4.1(6) . . . . ? C29 C24 N2 C20 175.6(4) . . . . ? C25 C24 N2 N3 175.2(4) . . . . ? C29 C24 N2 N3 -5.1(5) . . . . ? C21 C22 N3 N2 0.1(4) . . . . ? C23 C22 N3 N2 176.2(3) . . . . ? C20 N2 N3 C22 -1.4(4) . . . . ? C24 N2 N3 C22 179.2(3) . . . . ?