#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:23:25 +0300 (Tue, 06 Oct 2020) $ #$Revision: 258016 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240582.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_7240582 loop_ _publ_author_name 'Patel, Divyang M.' 'Patel, Hetal J.' 'Padr\'on, Jos\'e M.' 'Patel, Hitendra M.' _publ_section_title ; A novel substrate directed multicomponent reaction for the syntheses of tetrahydro-spiro[pyrazolo[4,3-f]quinoline]-8,5′-pyrimidines and tetrahydro-pyrazolo[4,3-f]pyrimido[4,5-b]quinolines via selective multiple C--C bond formation under metal-free conditions ; _journal_issue 33 _journal_name_full 'RSC Advances' _journal_page_first 19600 _journal_page_last 19609 _journal_paper_doi 10.1039/D0RA02990D _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C18 H12 BR N5 O2' _chemical_formula_sum 'C18 H12 Br N5 O2' _chemical_formula_weight 410.24 _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-2018/3 _audit_update_record ; 2020-03-13 deposited with the CCDC. 2020-05-08 downloaded from the CCDC. ; _cell_angle_alpha 94.851(4) _cell_angle_beta 97.256(4) _cell_angle_gamma 111.253(3) _cell_formula_units_Z 2 _cell_length_a 10.1063(13) _cell_length_b 10.6214(12) _cell_length_c 12.8286(16) _cell_measurement_reflns_used 3708 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 26.5 _cell_measurement_theta_min 2.2 _cell_volume 1260.4(3) _computing_cell_refinement 'SAINT V8.38A (BRUKER AXS INC.,2017)' _computing_data_collection 'APEX3 INC. BRUKER SOFTWARE PACKAGE' _computing_data_reduction 'SAINT V8.38A (BRUKER AXS INC.,2017)' _computing_molecular_graphics 'ORTEP3 MERCURY AND PLATON' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT-2014/5 (SHELDRICK,2014)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'BRUKER D8 VENTURE,PHOTON 200' _diffrn_measurement_method 'PHI AND OMEGA SCAN' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0590 _diffrn_reflns_av_unetI/netI 0.0403 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 36113 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.494 _diffrn_reflns_theta_min 2.194 _diffrn_source 'FINE FOCUS SEALED TUBE' _exptl_absorpt_coefficient_mu 1.647 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS-2016/2' _exptl_crystal_colour YELLOW _exptl_crystal_density_diffrn 1.081 _exptl_crystal_density_meas 1.081 _exptl_crystal_density_method 'NOT MEASURED' _exptl_crystal_description 'BLOCK TYPE' _exptl_crystal_F_000 412 _exptl_crystal_size_max 0.319 _exptl_crystal_size_mid 0.296 _exptl_crystal_size_min 0.258 _exptl_transmission_factor_max 0.7454 _exptl_transmission_factor_min 0.4850 _platon_squeeze_details ; ; _refine_diff_density_max 0.733 _refine_diff_density_min -0.695 _refine_diff_density_rms 0.080 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 5181 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0584 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1160P)^2^+0.1783P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1734 _refine_ls_wR_factor_ref 0.1865 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3708 _reflns_number_total 5181 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra02990d2.cif _cod_data_source_block shelx_CCDC2 _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 7240580--7240582.cif. ; _cod_database_code 7240582 _shelx_shelxl_version_number 2018/3 _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 ; TITL SIR97 run in space group P -1 shelx.res created by SHELXL-2018/3 at 10:58:08 on 13-Mar-2020 CELL 0.71073 10.1063 10.6214 12.8286 94.851 97.256 111.253 ZERR 2.00 0.0013 0.0012 0.0016 0.004 0.004 0.003 LATT 1 SFAC C H N O BR UNIT 36 24 10 4 2 MERG 2 FMAP 2 PLAN 25 ACTA BOND $H CONF LIST 6 L.S. 10 TEMP 20.00 WGHT 0.116000 0.178300 FVAR 2.56502 BR1 5 0.475031 0.651548 0.586892 11.00000 0.09848 0.13473 = 0.06187 -0.02736 -0.03687 0.06859 O1 4 -0.044103 0.672764 0.330578 11.00000 0.05279 0.07221 = 0.05186 -0.02036 -0.01186 0.03413 C4 1 -0.211899 0.452953 0.080648 11.00000 0.03744 0.04810 = 0.03997 0.00061 0.00349 0.02008 N2 3 -0.328879 0.492678 0.064117 11.00000 0.04317 0.06241 = 0.04143 -0.01046 -0.00733 0.02754 AFIX 43 H2 2 -0.390611 0.456823 0.006790 11.00000 -1.20000 AFIX 0 N3 3 -0.206041 0.364628 0.005788 11.00000 0.04483 0.05772 = 0.03732 -0.00603 -0.00437 0.02264 AFIX 43 H3 2 -0.270335 0.335296 -0.050642 11.00000 -1.20000 AFIX 0 C12 1 0.003657 0.464162 0.190856 11.00000 0.03694 0.04552 = 0.03677 0.00744 0.00606 0.01546 AFIX 13 H12 2 0.061664 0.537919 0.155305 11.00000 -1.20000 AFIX 0 C1 1 -0.109914 0.508390 0.174662 11.00000 0.03695 0.04572 = 0.03697 0.00071 0.00336 0.01776 N1 3 -0.250099 0.638966 0.222158 11.00000 0.04307 0.06365 = 0.04745 -0.01408 -0.00381 0.03041 AFIX 43 H1 2 -0.264371 0.696361 0.266337 11.00000 -1.20000 AFIX 0 C5 1 -0.095848 0.320707 0.019693 11.00000 0.05045 0.04802 = 0.04186 0.00281 0.00743 0.02401 O2 4 -0.456163 0.616141 0.117098 11.00000 0.04773 0.07890 = 0.06648 -0.01952 -0.01226 0.03825 C11 1 0.011619 0.366385 0.112290 11.00000 0.04185 0.04755 = 0.04142 0.00459 0.00877 0.02144 C2 1 -0.127315 0.612306 0.249470 11.00000 0.03646 0.05225 = 0.03887 -0.00296 0.00008 0.02022 C3 1 -0.352021 0.583767 0.132044 11.00000 0.04094 0.05768 = 0.04606 -0.00603 -0.00172 0.02441 C10 1 0.120383 0.308067 0.119079 11.00000 0.05412 0.05501 = 0.05025 0.00914 0.01398 0.02853 C13 1 0.116319 0.514595 0.287489 11.00000 0.04150 0.05516 = 0.03713 0.00079 0.00492 0.02768 C18 1 0.253246 0.606878 0.284187 11.00000 0.04287 0.06015 = 0.04884 0.00727 0.00391 0.01913 AFIX 43 H18 2 0.273704 0.641389 0.221312 11.00000 -1.20000 AFIX 0 C14 1 0.089034 0.462593 0.381849 11.00000 0.05139 0.07456 = 0.04548 0.00834 0.01046 0.03244 AFIX 43 H14 2 -0.002018 0.399540 0.385143 11.00000 -1.20000 AFIX 0 C6 1 -0.092874 0.224047 -0.063605 11.00000 0.06899 0.05931 = 0.04655 -0.00585 0.00602 0.03038 AFIX 43 H6 2 -0.164011 0.196566 -0.123622 11.00000 -1.20000 AFIX 0 N5 3 0.305528 0.238670 0.156016 11.00000 0.07695 0.09707 = 0.09869 0.00303 0.00767 0.06130 C17 1 0.360023 0.648598 0.372655 11.00000 0.04205 0.06633 = 0.06661 -0.00230 -0.00773 0.02131 AFIX 43 H17 2 0.451482 0.711075 0.369639 11.00000 -1.20000 AFIX 0 C8 1 0.116074 0.213799 0.033666 11.00000 0.06326 0.05830 = 0.06657 0.00714 0.02135 0.03552 C9 1 0.243458 0.318671 0.191660 11.00000 0.06736 0.08390 = 0.07205 0.00389 0.00458 0.05176 AFIX 43 H9 2 0.276019 0.375367 0.256479 11.00000 -1.20000 AFIX 0 C15 1 0.194196 0.502783 0.470081 11.00000 0.07773 0.09836 = 0.03553 0.00821 0.00756 0.05654 AFIX 43 H15 2 0.175196 0.467475 0.532898 11.00000 -1.20000 AFIX 0 C16 1 0.329842 0.597296 0.464059 11.00000 0.06217 0.08452 = 0.04387 -0.00936 -0.00814 0.04761 C7 1 0.011355 0.171423 -0.057157 11.00000 0.07805 0.06087 = 0.05961 -0.00459 0.01897 0.03723 AFIX 43 H7 2 0.012728 0.108846 -0.111873 11.00000 -1.20000 AFIX 0 N4 3 0.227659 0.175441 0.059919 11.00000 0.07818 0.08259 = 0.09209 0.00313 0.02205 0.05723 AFIX 43 H4 2 0.247087 0.117389 0.020093 11.00000 -1.20000 AFIX 0 HKLF 4 REM SIR97 run in space group P -1 REM wR2 = 0.1865, GooF = S = 1.053, Restrained GooF = 1.053 for all data REM R1 = 0.0584 for 3708 Fo > 4sig(Fo) and 0.0795 for all 5181 data REM 235 parameters refined using 0 restraints END WGHT 0.1160 0.1783 REM Highest difference peak 0.733, deepest hole -0.695, 1-sigma level 0.080 Q1 1 0.4031 0.5652 0.6018 11.00000 0.05 0.73 Q2 1 0.3988 0.6589 0.6233 11.00000 0.05 0.58 Q3 1 0.4638 0.7300 0.5820 11.00000 0.05 0.36 Q4 1 -0.1090 0.5637 0.2005 11.00000 0.05 0.29 Q5 1 -0.1580 0.4724 0.1466 11.00000 0.05 0.25 Q6 1 -0.2011 0.7195 0.1943 11.00000 0.05 0.24 Q7 1 -0.0180 -0.0488 -0.3663 11.00000 0.05 0.24 Q8 1 0.0937 0.1229 0.3479 11.00000 0.05 0.23 Q9 1 -0.0858 0.7583 0.2199 11.00000 0.05 0.21 Q10 1 0.1205 0.2817 0.0686 11.00000 0.05 0.21 Q11 1 -0.2732 0.8397 0.3834 11.00000 0.05 0.20 Q12 1 -0.1489 0.8854 0.5255 11.00000 0.05 0.20 Q13 1 -0.2621 0.7816 0.3162 11.00000 0.05 0.20 Q14 1 0.2007 0.0387 -0.1441 11.00000 0.05 0.20 Q15 1 0.6980 0.8775 0.4141 11.00000 0.05 0.20 Q16 1 0.1525 0.0800 0.3996 11.00000 0.05 0.20 Q17 1 0.1145 0.2570 -0.1454 11.00000 0.05 0.20 Q18 1 0.2940 0.0549 -0.0800 11.00000 0.05 0.19 Q19 1 -0.3371 0.5340 0.0974 11.00000 0.05 0.19 Q20 1 0.6810 1.0413 0.5134 11.00000 0.05 0.19 Q21 1 -0.1408 -0.0395 -0.2945 11.00000 0.05 0.19 Q22 1 0.7829 0.8748 0.5295 11.00000 0.05 0.19 Q23 1 0.3979 0.0545 -0.0043 11.00000 0.05 0.19 Q24 1 -0.3460 0.7179 0.0907 11.00000 0.05 0.19 Q25 1 0.1802 1.0457 0.4449 11.00000 0.05 0.19 ; _shelx_res_checksum 80002 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 0.47503(5) 0.65155(5) 0.58689(3) 0.0986(3) Uani 1 1 d . . . . . O1 O -0.0441(2) 0.6728(2) 0.33058(17) 0.0597(6) Uani 1 1 d . . . . . C4 C -0.2119(3) 0.4530(3) 0.0806(2) 0.0413(6) Uani 1 1 d . . . . . N2 N -0.3289(2) 0.4927(2) 0.06412(18) 0.0493(6) Uani 1 1 d . . . . . H2 H -0.390611 0.456823 0.006790 0.059 Uiso 1 1 calc R U . . . N3 N -0.2060(2) 0.3646(2) 0.00579(18) 0.0475(5) Uani 1 1 d . . . . . H3 H -0.270335 0.335296 -0.050642 0.057 Uiso 1 1 calc R U . . . C12 C 0.0037(3) 0.4642(3) 0.1909(2) 0.0397(5) Uani 1 1 d . . . . . H12 H 0.061664 0.537919 0.155305 0.048 Uiso 1 1 calc R U . . . C1 C -0.1099(3) 0.5084(3) 0.1747(2) 0.0399(5) Uani 1 1 d . . . . . N1 N -0.2501(2) 0.6390(2) 0.22216(19) 0.0509(6) Uani 1 1 d . . . . . H1 H -0.264371 0.696361 0.266337 0.061 Uiso 1 1 calc R U . . . C5 C -0.0958(3) 0.3207(3) 0.0197(2) 0.0455(6) Uani 1 1 d . . . . . O2 O -0.4562(2) 0.6161(2) 0.11710(19) 0.0642(6) Uani 1 1 d . . . . . C11 C 0.0116(3) 0.3664(3) 0.1123(2) 0.0423(6) Uani 1 1 d . . . . . C2 C -0.1273(3) 0.6123(3) 0.2495(2) 0.0427(6) Uani 1 1 d . . . . . C3 C -0.3520(3) 0.5838(3) 0.1320(2) 0.0483(6) Uani 1 1 d . . . . . C10 C 0.1204(3) 0.3081(3) 0.1191(2) 0.0503(7) Uani 1 1 d . . . . . C13 C 0.1163(3) 0.5146(3) 0.2875(2) 0.0424(6) Uani 1 1 d . . . . . C18 C 0.2532(3) 0.6069(3) 0.2842(2) 0.0511(7) Uani 1 1 d . . . . . H18 H 0.273704 0.641389 0.221312 0.061 Uiso 1 1 calc R U . . . C14 C 0.0890(3) 0.4626(3) 0.3818(2) 0.0545(7) Uani 1 1 d . . . . . H14 H -0.002018 0.399540 0.385143 0.065 Uiso 1 1 calc R U . . . C6 C -0.0929(4) 0.2240(3) -0.0636(2) 0.0577(7) Uani 1 1 d . . . . . H6 H -0.164011 0.196566 -0.123622 0.069 Uiso 1 1 calc R U . . . N5 N 0.3055(4) 0.2387(4) 0.1560(3) 0.0841(10) Uani 1 1 d . . . . . C17 C 0.3600(3) 0.6486(3) 0.3727(3) 0.0604(8) Uani 1 1 d . . . . . H17 H 0.451482 0.711075 0.369639 0.072 Uiso 1 1 calc R U . . . C8 C 0.1161(4) 0.2138(3) 0.0337(3) 0.0583(8) Uani 1 1 d . . . . . C9 C 0.2435(4) 0.3187(4) 0.1917(3) 0.0689(9) Uani 1 1 d . . . . . H9 H 0.276019 0.375367 0.256479 0.083 Uiso 1 1 calc R U . . . C15 C 0.1942(4) 0.5028(4) 0.4701(2) 0.0642(9) Uani 1 1 d . . . . . H15 H 0.175196 0.467475 0.532898 0.077 Uiso 1 1 calc R U . . . C16 C 0.3298(4) 0.5973(4) 0.4641(3) 0.0606(8) Uani 1 1 d . . . . . C7 C 0.0114(4) 0.1714(3) -0.0572(3) 0.0632(8) Uani 1 1 d . . . . . H7 H 0.012728 0.108846 -0.111873 0.076 Uiso 1 1 calc R U . . . N4 N 0.2277(3) 0.1754(3) 0.0599(3) 0.0765(9) Uani 1 1 d . . . . . H4 H 0.247087 0.117389 0.020093 0.092 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 0.0985(4) 0.1347(5) 0.0619(3) -0.0274(2) -0.0369(2) 0.0686(3) O1 0.0528(11) 0.0722(13) 0.0519(12) -0.0204(10) -0.0119(9) 0.0341(10) C4 0.0374(13) 0.0481(14) 0.0400(13) 0.0006(11) 0.0035(11) 0.0201(11) N2 0.0432(12) 0.0624(14) 0.0414(13) -0.0105(10) -0.0073(10) 0.0275(10) N3 0.0448(12) 0.0577(13) 0.0373(12) -0.0060(9) -0.0044(9) 0.0226(10) C12 0.0369(12) 0.0455(13) 0.0368(13) 0.0074(10) 0.0061(10) 0.0155(10) C1 0.0370(12) 0.0457(14) 0.0370(13) 0.0007(10) 0.0034(10) 0.0178(10) N1 0.0431(12) 0.0636(14) 0.0474(13) -0.0141(10) -0.0038(10) 0.0304(11) C5 0.0504(15) 0.0480(15) 0.0419(14) 0.0028(11) 0.0074(12) 0.0240(12) O2 0.0477(11) 0.0789(14) 0.0665(14) -0.0195(11) -0.0123(10) 0.0382(10) C11 0.0419(13) 0.0476(14) 0.0414(14) 0.0046(11) 0.0088(11) 0.0214(11) C2 0.0365(12) 0.0522(15) 0.0389(14) -0.0030(11) 0.0001(11) 0.0202(11) C3 0.0409(14) 0.0577(16) 0.0461(15) -0.0060(12) -0.0017(11) 0.0244(12) C10 0.0541(16) 0.0550(16) 0.0502(16) 0.0091(12) 0.0140(13) 0.0285(13) C13 0.0415(14) 0.0552(15) 0.0371(13) 0.0008(11) 0.0049(11) 0.0277(12) C18 0.0429(15) 0.0601(17) 0.0488(16) 0.0073(13) 0.0039(12) 0.0191(12) C14 0.0514(16) 0.0746(19) 0.0455(16) 0.0083(14) 0.0105(13) 0.0324(14) C6 0.0690(19) 0.0593(18) 0.0465(16) -0.0058(13) 0.0060(14) 0.0304(15) N5 0.077(2) 0.097(2) 0.099(3) 0.0030(19) 0.0077(19) 0.0613(18) C17 0.0420(15) 0.0663(19) 0.067(2) -0.0023(15) -0.0077(14) 0.0213(13) C8 0.0633(18) 0.0583(18) 0.067(2) 0.0071(14) 0.0214(16) 0.0355(15) C9 0.067(2) 0.084(2) 0.072(2) 0.0039(17) 0.0046(17) 0.0518(18) C15 0.078(2) 0.098(2) 0.0355(15) 0.0082(15) 0.0076(15) 0.057(2) C16 0.0622(19) 0.085(2) 0.0439(16) -0.0094(14) -0.0081(14) 0.0476(17) C7 0.078(2) 0.0609(19) 0.0596(19) -0.0046(14) 0.0190(17) 0.0372(16) N4 0.0782(19) 0.083(2) 0.092(2) 0.0031(17) 0.0220(18) 0.0572(17) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _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 N3 C4 N2 116.0(2) . . ? N3 C4 C1 124.8(2) . . ? N2 C4 C1 119.2(2) . . ? C3 N2 C4 124.4(2) . . ? C3 N2 H2 117.8 . . ? C4 N2 H2 117.8 . . ? C4 N3 C5 118.0(2) . . ? C4 N3 H3 121.0 . . ? C5 N3 H3 121.0 . . ? C1 C12 C11 118.5(2) . . ? C1 C12 C13 122.7(2) . . ? C11 C12 C13 118.8(2) . . ? C1 C12 H12 90.1 . . ? C11 C12 H12 90.1 . . ? C13 C12 H12 90.1 . . ? C12 C1 C4 118.1(2) . . ? C12 C1 C2 123.4(2) . . ? C4 C1 C2 118.5(2) . . ? C3 N1 C2 127.1(2) . . ? C3 N1 H1 116.5 . . ? C2 N1 H1 116.5 . . ? N3 C5 C11 122.4(2) . . ? N3 C5 C6 116.6(3) . . ? C11 C5 C6 121.0(3) . . ? C12 C11 C5 118.1(2) . . ? C12 C11 C10 125.0(3) . . ? C5 C11 C10 117.0(2) . . ? O1 C2 N1 119.6(2) . . ? O1 C2 C1 125.3(2) . . ? N1 C2 C1 115.0(2) . . ? O2 C3 N2 123.6(3) . . ? O2 C3 N1 120.7(2) . . ? N2 C3 N1 115.7(2) . . ? C8 C10 C9 103.5(3) . . ? C8 C10 C11 118.6(3) . . ? C9 C10 C11 137.9(3) . . ? C18 C13 C14 118.4(3) . . ? C18 C13 C12 121.1(2) . . ? C14 C13 C12 120.4(2) . . ? C17 C18 C13 121.1(3) . . ? C17 C18 H18 119.4 . . ? C13 C18 H18 119.4 . . ? C15 C14 C13 121.0(3) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C7 C6 C5 121.5(3) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C9 N5 N4 106.0(3) . . ? C16 C17 C18 119.2(3) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? N4 C8 C7 129.5(3) . . ? N4 C8 C10 106.6(3) . . ? C7 C8 C10 123.8(3) . . ? N5 C9 C10 111.6(4) . . ? N5 C9 H9 124.2 . . ? C10 C9 H9 124.2 . . ? C14 C15 C16 118.9(3) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C17 C16 C15 121.4(3) . . ? C17 C16 Br1 120.2(3) . . ? C15 C16 Br1 118.4(3) . . ? C6 C7 C8 118.1(3) . . ? C6 C7 H7 121.0 . . ? C8 C7 H7 121.0 . . ? C8 N4 N5 112.2(3) . . ? C8 N4 H4 123.9 . . ? N5 N4 H4 123.9 . . ? 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 C16 1.902(3) . ? O1 C2 1.215(3) . ? C4 N3 1.307(3) . ? C4 N2 1.391(3) . ? C4 C1 1.411(4) . ? N2 C3 1.350(4) . ? N2 H2 0.8600 . ? N3 C5 1.353(3) . ? N3 H3 0.8600 . ? C12 C1 1.389(4) . ? C12 C11 1.416(4) . ? C12 C13 1.486(4) . ? C12 H12 0.9800 . ? C1 C2 1.475(3) . ? N1 C3 1.374(3) . ? N1 C2 1.380(3) . ? N1 H1 0.8600 . ? C5 C11 1.422(4) . ? C5 C6 1.429(4) . ? O2 C3 1.219(3) . ? C11 C10 1.442(4) . ? C10 C8 1.406(4) . ? C10 C9 1.419(5) . ? C13 C18 1.384(4) . ? C13 C14 1.390(4) . ? C18 C17 1.381(4) . ? C18 H18 0.9300 . ? C14 C15 1.371(4) . ? C14 H14 0.9300 . ? C6 C7 1.357(5) . ? C6 H6 0.9300 . ? N5 C9 1.311(4) . ? N5 N4 1.350(5) . ? C17 C16 1.358(5) . ? C17 H17 0.9300 . ? C8 N4 1.346(4) . ? C8 C7 1.391(5) . ? C9 H9 0.9300 . ? C15 C16 1.391(5) . ? C15 H15 0.9300 . ? C7 H7 0.9300 . ? N4 H4 0.8600 . ? 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 N3 C4 N2 C3 -179.3(3) . . . . ? C1 C4 N2 C3 0.9(4) . . . . ? N2 C4 N3 C5 -178.5(2) . . . . ? C1 C4 N3 C5 1.3(4) . . . . ? C11 C12 C1 C4 0.2(4) . . . . ? C13 C12 C1 C4 -179.3(2) . . . . ? C11 C12 C1 C2 -178.4(2) . . . . ? C13 C12 C1 C2 2.1(4) . . . . ? N3 C4 C1 C12 -1.6(4) . . . . ? N2 C4 C1 C12 178.1(2) . . . . ? N3 C4 C1 C2 177.0(3) . . . . ? N2 C4 C1 C2 -3.2(4) . . . . ? C4 N3 C5 C11 0.4(4) . . . . ? C4 N3 C5 C6 179.9(3) . . . . ? C1 C12 C11 C5 1.3(4) . . . . ? C13 C12 C11 C5 -179.1(2) . . . . ? C1 C12 C11 C10 -178.2(3) . . . . ? C13 C12 C11 C10 1.4(4) . . . . ? N3 C5 C11 C12 -1.7(4) . . . . ? C6 C5 C11 C12 178.9(3) . . . . ? N3 C5 C11 C10 177.8(3) . . . . ? C6 C5 C11 C10 -1.6(4) . . . . ? C3 N1 C2 O1 177.5(3) . . . . ? C3 N1 C2 C1 -2.9(4) . . . . ? C12 C1 C2 O1 2.2(4) . . . . ? C4 C1 C2 O1 -176.4(3) . . . . ? C12 C1 C2 N1 -177.4(3) . . . . ? C4 C1 C2 N1 4.0(4) . . . . ? C4 N2 C3 O2 -179.0(3) . . . . ? C4 N2 C3 N1 0.4(4) . . . . ? C2 N1 C3 O2 -179.9(3) . . . . ? C2 N1 C3 N2 0.7(4) . . . . ? C12 C11 C10 C8 -178.8(3) . . . . ? C5 C11 C10 C8 1.7(4) . . . . ? C12 C11 C10 C9 0.1(5) . . . . ? C5 C11 C10 C9 -179.4(3) . . . . ? C1 C12 C13 C18 -105.1(3) . . . . ? C11 C12 C13 C18 75.3(3) . . . . ? C1 C12 C13 C14 79.3(3) . . . . ? C11 C12 C13 C14 -100.3(3) . . . . ? C14 C13 C18 C17 -1.1(4) . . . . ? C12 C13 C18 C17 -176.8(3) . . . . ? C18 C13 C14 C15 0.9(4) . . . . ? C12 C13 C14 C15 176.5(3) . . . . ? N3 C5 C6 C7 -178.9(3) . . . . ? C11 C5 C6 C7 0.6(5) . . . . ? C13 C18 C17 C16 0.4(5) . . . . ? C9 C10 C8 N4 0.9(3) . . . . ? C11 C10 C8 N4 -179.9(3) . . . . ? C9 C10 C8 C7 179.9(3) . . . . ? C11 C10 C8 C7 -1.0(5) . . . . ? N4 N5 C9 C10 0.8(4) . . . . ? C8 C10 C9 N5 -1.1(4) . . . . ? C11 C10 C9 N5 180.0(4) . . . . ? C13 C14 C15 C16 0.1(4) . . . . ? C18 C17 C16 C15 0.6(5) . . . . ? C18 C17 C16 Br1 179.5(2) . . . . ? C14 C15 C16 C17 -0.8(5) . . . . ? C14 C15 C16 Br1 -179.7(2) . . . . ? C5 C6 C7 C8 0.3(5) . . . . ? N4 C8 C7 C6 178.6(3) . . . . ? C10 C8 C7 C6 -0.1(5) . . . . ? C7 C8 N4 N5 -179.4(3) . . . . ? C10 C8 N4 N5 -0.5(4) . . . . ? C9 N5 N4 C8 -0.2(4) . . . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.071 0.000 0.415 524 101 ' '