#------------------------------------------------------------------------------ #$Date: 2026-05-04 14:11:28 +0100 (Mon, 04 May 2026) $ #$Revision: 305706 $ #$URL: svn://www.crystallography.net/cod/cif/7/72/09/7720980.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_7720980 loop_ _publ_author_name 'Balayan, Kajal' 'Biswas, Arindam' 'Sharma, Himanshu' 'Tiwari, Prabhakar' 'Vanka, Kumar' 'Gonnade, Rajesh G.' 'Rath, Arup K.' 'Sen, Sakya S.' _publ_section_title ; Unveiling the reactivity of N-heterocyclic methylene hydrazines. ; _journal_issue 14 _journal_name_full 'Dalton transactions (Cambridge, England : 2003)' _journal_page_first 5432 _journal_page_last 5436 _journal_paper_doi 10.1039/d6dt00611f _journal_volume 55 _journal_year 2026 _chemical_formula_moiety '2(C12 H23 N4 Cl), 0.75 (H2 O)' _chemical_formula_sum 'C24 H47.5 Cl2 N8 O0.75' _chemical_formula_weight 531.10 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary 'difference Fourier' _audit_creation_method SHELXL-2019/3 _audit_update_record ; 2026-02-08 deposited with the CCDC. 2026-03-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.906(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.5515(12) _cell_length_b 11.5612(13) _cell_length_c 21.090(2) _cell_measurement_reflns_used 9826 _cell_measurement_temperature 201(2) _cell_measurement_theta_max 27.89 _cell_measurement_theta_min 2.56 _cell_volume 3058.7(5) _computing_cell_refinement 'SAINT (Bruker, 2016)' _computing_data_collection 'APEX3 (Bruker, 2016)' _computing_data_reduction 'SAINT (Bruker, 2016)' _computing_molecular_graphics 'Bruker SHELXTL, Mercury 2020.20' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 201(2) _diffrn_detector 'Photon II CPAD Area Detector' _diffrn_detector_area_resol_mean 7.39 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'multilayer mirrors' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0707 _diffrn_reflns_av_unetI/netI 0.0286 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 87615 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.500 _diffrn_reflns_theta_min 1.861 _diffrn_source 'micro-focus sealed tube' _diffrn_source_type 'Incoatech I\mS HB' _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_T_max 0.1504 _exptl_absorpt_correction_T_min 0.1118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.153 _exptl_crystal_description block _exptl_crystal_F_000 1150 _exptl_crystal_size_max 0.190 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.790 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 337 _refine_ls_number_reflns 5672 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.102 _refine_ls_R_factor_all 0.0796 _refine_ls_R_factor_gt 0.0701 _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^)+(0.0831P)^2^+3.1623P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1901 _refine_ls_wR_factor_ref 0.1991 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4793 _reflns_number_total 5672 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6dt00611f2.cif _cod_data_source_block mo_KB_ItbuNNCH2salt_2_a _cod_depositor_comments ; The following automatic conversions were performed: data item '_atom_sites_solution_primary' value 'direct method' was changed to 'direct'. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_original_cell_volume 3058.7(6) _cod_original_sg_symbol_H-M 'P 21/n' _cod_original_formula_sum 'C24 H47.50 Cl2 N8 O0.75' _cod_database_code 7720980 _shelx_shelxl_version_number 2019/3 _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_estimated_absorpt_t_min 0.956 _shelx_estimated_absorpt_t_max 0.988 _shelx_res_file ; TITL mo_KB_ItbuNNCH2salt_2_a.res in P2(1)/n mo_KB_ItbuNNCH2salt_2_a.res created by SHELXL-2019/3 at 17:31:44 on 08-Feb-2026 REM Old TITL mo_KB_ItbuNNCH2salt_2 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.186, Rweak 0.014, Alpha 0.043 REM 0.910 for 330 systematic absences, Orientation as input REM Formula found by SHELXT: C25 Cl2 N8 CELL 0.71073 12.5515 11.5612 21.0899 90 91.906 90 ZERR 4 0.0012 0.0013 0.0022 0 0.003 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Cl N O UNIT 96 190 8 32 3 L.S. 10 PLAN 20 SIZE 0.19 0.11 0.05 TEMP -72.15 CONF ACTA LIST 4 BOND $H HTAB FMAP 2 MORE -1 OMIT -3 51 OMIT 3 1 0 OMIT 1 5 12 OMIT 0 1 1 OMIT 1 0 1 OMIT 2 0 0 OMIT 1 1 0 OMIT 2 2 1 OMIT 0 2 0 WGHT 0.083100 3.162300 FVAR 0.66516 MOLE 1 CL1 3 0.572891 -0.022933 0.622294 11.00000 0.04963 0.07615 = 0.05818 0.00724 -0.00368 -0.00594 N1 4 0.903403 0.256615 0.632898 11.00000 0.03923 0.05015 = 0.03684 -0.00269 0.00157 -0.00648 N2 4 0.854527 0.190423 0.724695 11.00000 0.03744 0.04630 = 0.03798 0.00002 0.00346 -0.00197 N3 4 0.812660 0.072432 0.632195 11.00000 0.03839 0.05418 = 0.05732 -0.01503 0.00457 -0.00702 H3 2 0.748028 0.057589 0.629423 11.00000 -1.50000 N4 4 0.886307 -0.013001 0.620534 11.00000 0.05509 0.06297 = 0.08015 -0.02654 0.01192 -0.00344 C1 1 0.853147 0.169261 0.661622 11.00000 0.03090 0.04784 = 0.04138 -0.00225 -0.00059 -0.00071 C2 1 0.906822 0.293667 0.735391 11.00000 0.04366 0.04677 = 0.03932 -0.00689 -0.00068 -0.00480 AFIX 43 H2 2 0.918871 0.330102 0.775363 11.00000 -1.20000 AFIX 0 C3 1 0.937717 0.333530 0.679039 11.00000 0.04693 0.04596 = 0.04255 -0.00350 -0.00153 -0.00972 AFIX 43 H3A 2 0.976492 0.402747 0.672227 11.00000 -1.20000 AFIX 0 C4 1 0.917571 0.283188 0.562948 11.00000 0.05119 0.06415 = 0.03500 0.00007 0.00336 -0.00973 C5 1 0.862017 0.397869 0.549989 11.00000 0.08697 0.09309 = 0.05357 0.01622 0.00284 0.01313 AFIX 137 H5A 2 0.866188 0.417060 0.504879 11.00000 -1.50000 H5B 2 0.896931 0.458688 0.575507 11.00000 -1.50000 H5C 2 0.787080 0.391867 0.561219 11.00000 -1.50000 AFIX 0 C6 1 0.871949 0.190542 0.518746 11.00000 0.13679 0.10370 = 0.03778 -0.00710 -0.00171 -0.04766 AFIX 137 H6A 2 0.880574 0.214355 0.474617 11.00000 -1.50000 H6B 2 0.796034 0.179989 0.526557 11.00000 -1.50000 H6C 2 0.909815 0.117526 0.526556 11.00000 -1.50000 AFIX 0 C7 1 1.036054 0.296133 0.553559 11.00000 0.06310 0.11071 = 0.05697 -0.00811 0.01967 -0.00601 AFIX 137 H7A 2 1.047927 0.322638 0.510225 11.00000 -1.50000 H7B 2 1.071272 0.221330 0.560496 11.00000 -1.50000 H7C 2 1.065647 0.352809 0.583879 11.00000 -1.50000 AFIX 0 C8 1 0.798233 0.122099 0.775209 11.00000 0.04515 0.05421 = 0.04062 0.00337 0.00707 -0.00177 C9 1 0.679107 0.139858 0.764497 11.00000 0.04327 0.08593 = 0.06009 0.00255 0.01371 -0.00323 AFIX 137 H9A 2 0.640952 0.102117 0.798615 11.00000 -1.50000 H9B 2 0.656379 0.106087 0.723627 11.00000 -1.50000 H9C 2 0.663118 0.222829 0.764336 11.00000 -1.50000 AFIX 0 C10 1 0.833508 0.168316 0.839774 11.00000 0.07544 0.08418 = 0.04476 0.00662 0.00244 -0.01662 AFIX 137 H10A 2 0.799939 0.123036 0.872939 11.00000 -1.50000 H10B 2 0.812202 0.249555 0.843273 11.00000 -1.50000 H10C 2 0.911199 0.162251 0.844873 11.00000 -1.50000 AFIX 0 C11 1 0.828389 -0.004877 0.770781 11.00000 0.08626 0.05745 = 0.07118 0.01725 0.02381 -0.00009 AFIX 137 H11A 2 0.800584 -0.046755 0.807091 11.00000 -1.50000 H11B 2 0.906188 -0.012207 0.771055 11.00000 -1.50000 H11C 2 0.797840 -0.037554 0.731341 11.00000 -1.50000 AFIX 0 C12 1 0.851002 -0.103603 0.594614 11.00000 0.08468 0.07109 = 0.10086 -0.03480 0.02889 -0.01154 AFIX 93 H12A 2 0.777090 -0.110566 0.584113 11.00000 -1.20000 H12B 2 0.898199 -0.165196 0.585502 11.00000 -1.20000 AFIX 0 MOLE 2 CL2 3 0.073129 0.599874 0.628197 11.00000 0.05431 0.05591 = 0.04572 -0.00185 -0.00047 -0.00609 N5 4 0.395296 0.335387 0.641537 11.00000 0.04561 0.05117 = 0.04588 0.01232 0.00482 0.00319 N6 4 0.354733 0.399155 0.735356 11.00000 0.03706 0.04902 = 0.04906 0.01432 0.00717 0.00303 N7 4 0.314531 0.524138 0.645555 11.00000 0.04486 0.05971 = 0.07156 0.02711 0.00884 0.01451 H7 2 0.248539 0.541089 0.635277 11.00000 -1.50000 N8 4 0.392098 0.604296 0.633306 11.00000 0.06206 0.05802 = 0.07757 0.02744 0.02227 0.00599 C13 1 0.350909 0.424095 0.672955 11.00000 0.03644 0.04630 = 0.05141 0.01563 0.00724 0.00492 C14 1 0.429523 0.255212 0.685999 11.00000 0.04769 0.04929 = 0.05995 0.01399 0.00219 0.00865 AFIX 43 H14 2 0.465582 0.184983 0.677393 11.00000 -1.20000 AFIX 0 C15 1 0.413288 0.319046 0.571768 11.00000 0.06520 0.07388 = 0.04640 0.00542 0.00496 0.00486 C16 1 0.403415 0.292960 0.743258 11.00000 0.04522 0.05182 = 0.05142 0.01821 0.00086 0.00343 AFIX 43 H16 2 0.416082 0.253753 0.782372 11.00000 -1.20000 AFIX 0 C17 1 0.349146 0.401969 0.530397 11.00000 0.17210 0.09966 = 0.05308 0.01687 -0.00805 0.03201 AFIX 137 H17A 2 0.347399 0.374251 0.486462 11.00000 -1.50000 H17B 2 0.382165 0.478751 0.532413 11.00000 -1.50000 H17C 2 0.276260 0.406703 0.545477 11.00000 -1.50000 AFIX 0 C18 1 0.531814 0.330078 0.563503 11.00000 0.08528 0.19118 = 0.07064 -0.00315 0.03683 -0.02104 AFIX 137 H18A 2 0.547893 0.317196 0.518900 11.00000 -1.50000 H18B 2 0.569315 0.272417 0.589985 11.00000 -1.50000 H18C 2 0.555209 0.407785 0.576255 11.00000 -1.50000 AFIX 0 C19 1 0.376010 0.198024 0.555315 11.00000 0.10949 0.09447 = 0.05962 -0.01164 -0.00203 0.01258 AFIX 137 H19A 2 0.383827 0.184369 0.509846 11.00000 -1.50000 H19B 2 0.300940 0.189533 0.565818 11.00000 -1.50000 H19C 2 0.419102 0.141729 0.579619 11.00000 -1.50000 AFIX 0 C20 1 0.303277 0.468140 0.787322 11.00000 0.04464 0.05277 = 0.05346 0.00553 0.01093 0.00124 C21 1 0.183468 0.452051 0.778746 11.00000 0.04498 0.08127 = 0.06221 0.00955 0.01312 0.00486 AFIX 137 H21A 2 0.147805 0.486686 0.814766 11.00000 -1.50000 H21B 2 0.166842 0.369296 0.776560 11.00000 -1.50000 H21C 2 0.158514 0.489798 0.739383 11.00000 -1.50000 AFIX 0 C22 1 0.335491 0.595113 0.783579 11.00000 0.08214 0.05925 = 0.08629 -0.00421 0.02635 -0.00904 AFIX 137 H22A 2 0.309681 0.636493 0.820605 11.00000 -1.50000 H22B 2 0.304149 0.629453 0.744783 11.00000 -1.50000 H22C 2 0.413340 0.600970 0.782944 11.00000 -1.50000 AFIX 0 C23 1 0.341888 0.418482 0.851082 11.00000 0.06513 0.08489 = 0.05678 0.00354 -0.00082 0.00320 AFIX 137 H23A 2 0.305617 0.457953 0.885373 11.00000 -1.50000 H23B 2 0.419017 0.430025 0.856411 11.00000 -1.50000 H23C 2 0.325821 0.335582 0.852403 11.00000 -1.50000 AFIX 0 C24 1 0.361385 0.697029 0.607145 11.00000 0.09552 0.05811 = 0.07131 0.02281 0.02877 0.01504 AFIX 93 H24A 2 0.287872 0.708634 0.596936 11.00000 -1.20000 H24B 2 0.411745 0.755328 0.597634 11.00000 -1.20000 AFIX 6 MOLE 3 O1 5 0.373753 0.923250 0.520566 10.75000 0.09969 0.08523 = 0.08219 0.01141 -0.00401 -0.03127 H1A 2 0.385043 0.948144 0.482440 10.75000 -1.50000 H1B 2 0.430579 0.934268 0.544544 10.75000 -1.50000 AFIX 0 HKLF 4 REM mo_KB_ItbuNNCH2salt_2_a.res in P2(1)/n REM wR2 = 0.1991, GooF = S = 1.102, Restrained GooF = 1.102 for all data REM R1 = 0.0701 for 4793 Fo > 4sig(Fo) and 0.0796 for all 5672 data REM 337 parameters refined using 0 restraints END WGHT 0.0831 3.1623 REM Instructions for potential hydrogen bonds HTAB N3 Cl1 EQIV $1 -x+3/2, y+1/2, -z+3/2 HTAB C2 Cl1_$1 EQIV $2 x+1, y, z HTAB C3 Cl2_$2 EQIV $3 -x+1, -y+1, -z+1 HTAB C5 Cl2_$3 HTAB C5 Cl2_$2 HTAB C6 O1_$3 HTAB C6 N4 HTAB C9 Cl1 EQIV $4 -x+3/2, y-1/2, -z+3/2 HTAB C10 N8_$4 HTAB C11 N3 HTAB C11 N4 HTAB C12 Cl1 HTAB N7 Cl2 EQIV $5 -x+1/2, y-1/2, -z+3/2 HTAB C16 Cl2_$5 HTAB C17 N8 HTAB C19 Cl1 HTAB C21 Cl2 HTAB C22 N7 HTAB C22 N8 HTAB C23 N4_$1 HTAB C24 O1 REM Highest difference peak 0.790, deepest hole -0.356, 1-sigma level 0.055 Q1 1 0.5721 -0.1085 0.6284 11.00000 0.05 0.79 Q2 1 0.0719 0.5203 0.6220 11.00000 0.05 0.68 Q3 1 0.3997 0.2523 0.6335 11.00000 0.05 0.41 Q4 1 0.4376 0.1766 0.6740 11.00000 0.05 0.34 Q5 1 1.0253 0.1956 0.5544 11.00000 0.05 0.31 Q6 1 0.3541 0.3160 0.7253 11.00000 0.05 0.31 Q7 1 0.9095 0.2170 0.7342 11.00000 0.05 0.30 Q8 1 0.3018 0.4444 0.6271 11.00000 0.05 0.30 Q9 1 0.3583 0.1020 0.5509 11.00000 0.05 0.29 Q10 1 0.3869 0.5271 0.6171 11.00000 0.05 0.29 Q11 1 0.5289 0.2227 0.5492 11.00000 0.05 0.27 Q12 1 0.9018 0.1788 0.6332 11.00000 0.05 0.27 Q13 1 0.4019 0.2212 0.7283 11.00000 0.05 0.26 Q14 1 0.8369 0.1122 0.5274 11.00000 0.05 0.26 Q15 1 0.3425 0.3542 0.6526 11.00000 0.05 0.26 Q16 1 0.8536 0.1132 0.7244 11.00000 0.05 0.26 Q17 1 0.8423 0.0925 0.6611 11.00000 0.05 0.24 Q18 1 0.8787 -0.0876 0.6259 11.00000 0.05 0.23 Q19 1 0.8252 0.3200 0.5460 11.00000 0.05 0.23 Q20 1 0.3379 0.3237 0.5163 11.00000 0.05 0.22 ; _shelx_res_checksum 8852 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 Cl1 Cl 0.57289(6) -0.02293(9) 0.62229(4) 0.0614(3) Uani 1 1 d . . . . . N1 N 0.90340(18) 0.2566(2) 0.63290(11) 0.0421(5) Uani 1 1 d . . . . . N2 N 0.85453(17) 0.1904(2) 0.72469(11) 0.0405(5) Uani 1 1 d . . . . . N3 N 0.8127(2) 0.0724(2) 0.63220(13) 0.0499(6) Uani 1 1 d . . . . . H3 H 0.748(3) 0.058(4) 0.6294(19) 0.075 Uiso 1 1 d . U . . . N4 N 0.8863(2) -0.0130(3) 0.62053(16) 0.0659(8) Uani 1 1 d . . . . . C1 C 0.8531(2) 0.1693(3) 0.66162(13) 0.0401(6) Uani 1 1 d . . . . . C2 C 0.9068(2) 0.2937(3) 0.73539(13) 0.0433(6) Uani 1 1 d . . . . . H2 H 0.918871 0.330102 0.775363 0.052 Uiso 1 1 calc R U . . . C3 C 0.9377(2) 0.3335(3) 0.67904(13) 0.0452(7) Uani 1 1 d . . . . . H3A H 0.976492 0.402747 0.672227 0.054 Uiso 1 1 calc R U . . . C4 C 0.9176(2) 0.2832(3) 0.56295(13) 0.0501(7) Uani 1 1 d . . . . . C5 C 0.8620(4) 0.3979(4) 0.54999(18) 0.0779(12) Uani 1 1 d . . . . . H5A H 0.866188 0.417060 0.504879 0.117 Uiso 1 1 calc R U . . . H5B H 0.896931 0.458688 0.575507 0.117 Uiso 1 1 calc R U . . . H5C H 0.787080 0.391867 0.561219 0.117 Uiso 1 1 calc R U . . . C6 C 0.8719(4) 0.1905(4) 0.51875(17) 0.0929(16) Uani 1 1 d . . . . . H6A H 0.880574 0.214355 0.474617 0.139 Uiso 1 1 calc R U . . . H6B H 0.796034 0.179989 0.526557 0.139 Uiso 1 1 calc R U . . . H6C H 0.909815 0.117526 0.526556 0.139 Uiso 1 1 calc R U . . . C7 C 1.0361(3) 0.2961(4) 0.55356(18) 0.0765(11) Uani 1 1 d . . . . . H7A H 1.047927 0.322638 0.510225 0.115 Uiso 1 1 calc R U . . . H7B H 1.071272 0.221330 0.560496 0.115 Uiso 1 1 calc R U . . . H7C H 1.065647 0.352809 0.583879 0.115 Uiso 1 1 calc R U . . . C8 C 0.7982(2) 0.1221(3) 0.77521(14) 0.0465(7) Uani 1 1 d . . . . . C9 C 0.6791(2) 0.1399(4) 0.76450(17) 0.0628(9) Uani 1 1 d . . . . . H9A H 0.640952 0.102117 0.798615 0.094 Uiso 1 1 calc R U . . . H9B H 0.656379 0.106087 0.723627 0.094 Uiso 1 1 calc R U . . . H9C H 0.663118 0.222829 0.764336 0.094 Uiso 1 1 calc R U . . . C10 C 0.8335(3) 0.1683(4) 0.83977(16) 0.0681(10) Uani 1 1 d . . . . . H10A H 0.799939 0.123036 0.872939 0.102 Uiso 1 1 calc R U . . . H10B H 0.812202 0.249555 0.843273 0.102 Uiso 1 1 calc R U . . . H10C H 0.911199 0.162251 0.844873 0.102 Uiso 1 1 calc R U . . . C11 C 0.8284(3) -0.0049(3) 0.77078(19) 0.0712(11) Uani 1 1 d . . . . . H11A H 0.800584 -0.046755 0.807091 0.107 Uiso 1 1 calc R U . . . H11B H 0.906188 -0.012207 0.771055 0.107 Uiso 1 1 calc R U . . . H11C H 0.797840 -0.037554 0.731341 0.107 Uiso 1 1 calc R U . . . C12 C 0.8510(4) -0.1036(4) 0.5946(2) 0.0850(13) Uani 1 1 d . . . . . H12A H 0.777090 -0.110566 0.584113 0.102 Uiso 1 1 calc R U . . . H12B H 0.898199 -0.165196 0.585502 0.102 Uiso 1 1 calc R U . . . Cl2 Cl 0.07313(6) 0.59987(7) 0.62820(3) 0.0520(2) Uani 1 1 d . . . . . N5 N 0.39530(19) 0.3354(2) 0.64154(12) 0.0475(6) Uani 1 1 d . . . . . N6 N 0.35473(18) 0.3992(2) 0.73536(12) 0.0449(6) Uani 1 1 d . . . . . N7 N 0.3145(2) 0.5241(3) 0.64555(15) 0.0586(8) Uani 1 1 d . . . . . H7 H 0.249(4) 0.541(4) 0.635(2) 0.088 Uiso 1 1 d . U . . . N8 N 0.3921(2) 0.6043(3) 0.63331(15) 0.0654(8) Uani 1 1 d . . . . . C13 C 0.3509(2) 0.4241(3) 0.67296(14) 0.0446(7) Uani 1 1 d . . . . . C14 C 0.4295(2) 0.2552(3) 0.68600(16) 0.0523(8) Uani 1 1 d . . . . . H14 H 0.465582 0.184983 0.677393 0.063 Uiso 1 1 calc R U . . . C15 C 0.4133(3) 0.3190(3) 0.57177(16) 0.0618(9) Uani 1 1 d . . . . . C16 C 0.4034(2) 0.2930(3) 0.74326(15) 0.0495(7) Uani 1 1 d . . . . . H16 H 0.416082 0.253753 0.782372 0.059 Uiso 1 1 calc R U . . . C17 C 0.3491(5) 0.4020(5) 0.5304(2) 0.1085(19) Uani 1 1 d . . . . . H17A H 0.347399 0.374251 0.486462 0.163 Uiso 1 1 calc R U . . . H17B H 0.382165 0.478751 0.532413 0.163 Uiso 1 1 calc R U . . . H17C H 0.276260 0.406703 0.545477 0.163 Uiso 1 1 calc R U . . . C18 C 0.5318(4) 0.3301(6) 0.5635(2) 0.115(2) Uani 1 1 d . . . . . H18A H 0.547893 0.317196 0.518900 0.172 Uiso 1 1 calc R U . . . H18B H 0.569315 0.272417 0.589985 0.172 Uiso 1 1 calc R U . . . H18C H 0.555209 0.407785 0.576255 0.172 Uiso 1 1 calc R U . . . C19 C 0.3760(4) 0.1980(4) 0.5553(2) 0.0880(13) Uani 1 1 d . . . . . H19A H 0.383827 0.184369 0.509846 0.132 Uiso 1 1 calc R U . . . H19B H 0.300940 0.189533 0.565818 0.132 Uiso 1 1 calc R U . . . H19C H 0.419102 0.141729 0.579619 0.132 Uiso 1 1 calc R U . . . C20 C 0.3033(2) 0.4681(3) 0.78732(15) 0.0501(7) Uani 1 1 d . . . . . C21 C 0.1835(3) 0.4521(4) 0.77875(17) 0.0626(9) Uani 1 1 d . . . . . H21A H 0.147805 0.486686 0.814766 0.094 Uiso 1 1 calc R U . . . H21B H 0.166842 0.369296 0.776560 0.094 Uiso 1 1 calc R U . . . H21C H 0.158514 0.489798 0.739383 0.094 Uiso 1 1 calc R U . . . C22 C 0.3355(3) 0.5951(3) 0.7836(2) 0.0754(11) Uani 1 1 d . . . . . H22A H 0.309681 0.636493 0.820605 0.113 Uiso 1 1 calc R U . . . H22B H 0.304149 0.629453 0.744783 0.113 Uiso 1 1 calc R U . . . H22C H 0.413340 0.600970 0.782944 0.113 Uiso 1 1 calc R U . . . C23 C 0.3419(3) 0.4185(4) 0.85108(17) 0.0690(10) Uani 1 1 d . . . . . H23A H 0.305617 0.457953 0.885373 0.103 Uiso 1 1 calc R U . . . H23B H 0.419017 0.430025 0.856411 0.103 Uiso 1 1 calc R U . . . H23C H 0.325821 0.335582 0.852403 0.103 Uiso 1 1 calc R U . . . C24 C 0.3614(4) 0.6970(3) 0.60714(18) 0.0744(11) Uani 1 1 d . . . . . H24A H 0.287872 0.708634 0.596936 0.089 Uiso 1 1 calc R U . . . H24B H 0.411745 0.755328 0.597634 0.089 Uiso 1 1 calc R U . . . O1 O 0.3738(4) 0.9233(4) 0.5206(2) 0.0892(12) Uani 0.75 1 d G . P . . H1A H 0.385043 0.948144 0.482440 0.134 Uiso 0.75 1 d G U P . . H1B H 0.430579 0.934268 0.544544 0.134 Uiso 0.75 1 d G U P . . 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 Cl1 0.0496(5) 0.0761(6) 0.0582(5) 0.0072(4) -0.0037(3) -0.0059(4) N1 0.0392(12) 0.0502(14) 0.0368(12) -0.0027(10) 0.0016(9) -0.0065(10) N2 0.0374(12) 0.0463(13) 0.0380(12) 0.0000(10) 0.0035(9) -0.0020(10) N3 0.0384(13) 0.0542(16) 0.0573(15) -0.0150(12) 0.0046(11) -0.0070(12) N4 0.0551(16) 0.0630(18) 0.080(2) -0.0265(16) 0.0119(14) -0.0034(14) C1 0.0309(12) 0.0478(16) 0.0414(14) -0.0022(12) -0.0006(10) -0.0007(11) C2 0.0437(15) 0.0468(16) 0.0393(14) -0.0069(12) -0.0007(11) -0.0048(12) C3 0.0469(15) 0.0460(16) 0.0425(15) -0.0035(12) -0.0015(12) -0.0097(13) C4 0.0512(17) 0.064(2) 0.0350(14) 0.0001(13) 0.0034(12) -0.0097(15) C5 0.087(3) 0.093(3) 0.054(2) 0.016(2) 0.0028(19) 0.013(2) C6 0.137(4) 0.104(3) 0.0378(18) -0.007(2) -0.002(2) -0.048(3) C7 0.063(2) 0.111(3) 0.057(2) -0.008(2) 0.0197(17) -0.006(2) C8 0.0451(15) 0.0542(18) 0.0406(15) 0.0034(13) 0.0071(12) -0.0018(13) C9 0.0433(17) 0.086(3) 0.060(2) 0.0026(19) 0.0137(14) -0.0032(17) C10 0.075(2) 0.084(3) 0.0448(18) 0.0066(17) 0.0024(16) -0.017(2) C11 0.086(3) 0.057(2) 0.071(2) 0.0172(18) 0.024(2) -0.0001(19) C12 0.085(3) 0.071(3) 0.101(3) -0.035(2) 0.029(2) -0.012(2) Cl2 0.0543(4) 0.0559(5) 0.0457(4) -0.0018(3) -0.0005(3) -0.0061(3) N5 0.0456(13) 0.0512(15) 0.0459(13) 0.0123(11) 0.0048(10) 0.0032(11) N6 0.0371(12) 0.0490(14) 0.0491(14) 0.0143(11) 0.0072(10) 0.0030(10) N7 0.0449(14) 0.0597(17) 0.0716(19) 0.0271(14) 0.0088(13) 0.0145(13) N8 0.0621(17) 0.0580(17) 0.078(2) 0.0274(15) 0.0223(15) 0.0060(14) C13 0.0364(14) 0.0463(16) 0.0514(17) 0.0156(13) 0.0072(12) 0.0049(12) C14 0.0477(16) 0.0493(18) 0.0599(19) 0.0140(15) 0.0022(14) 0.0087(14) C15 0.065(2) 0.074(2) 0.0464(18) 0.0054(16) 0.0050(15) 0.0049(18) C16 0.0452(16) 0.0518(18) 0.0514(17) 0.0182(14) 0.0009(13) 0.0034(13) C17 0.172(5) 0.100(4) 0.053(2) 0.017(2) -0.008(3) 0.032(4) C18 0.085(3) 0.191(6) 0.071(3) -0.003(3) 0.037(2) -0.021(4) C19 0.109(4) 0.094(3) 0.060(2) -0.012(2) -0.002(2) 0.013(3) C20 0.0446(16) 0.0528(18) 0.0535(18) 0.0055(14) 0.0109(13) 0.0012(13) C21 0.0450(17) 0.081(2) 0.062(2) 0.0095(18) 0.0131(15) 0.0049(17) C22 0.082(3) 0.059(2) 0.086(3) -0.004(2) 0.026(2) -0.0090(19) C23 0.065(2) 0.085(3) 0.057(2) 0.0035(19) -0.0008(17) 0.0032(19) C24 0.096(3) 0.058(2) 0.071(2) 0.0228(19) 0.029(2) 0.015(2) O1 0.100(3) 0.085(3) 0.082(3) 0.011(2) -0.004(2) -0.031(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' Cl Cl 0.1484 0.1585 '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 C1 N1 C3 107.9(2) . . ? C1 N1 C4 131.2(2) . . ? C3 N1 C4 120.7(2) . . ? C1 N2 C2 108.0(2) . . ? C1 N2 C8 127.2(2) . . ? C2 N2 C8 124.5(2) . . ? C1 N3 N4 115.2(2) . . ? C1 N3 H3 123(3) . . ? N4 N3 H3 120(3) . . ? C12 N4 N3 116.5(3) . . ? N1 C1 N2 108.4(2) . . ? N1 C1 N3 125.6(3) . . ? N2 C1 N3 125.9(3) . . ? C3 C2 N2 107.6(2) . . ? C3 C2 H2 126.2 . . ? N2 C2 H2 126.2 . . ? C2 C3 N1 108.1(3) . . ? C2 C3 H3A 125.9 . . ? N1 C3 H3A 125.9 . . ? C7 C4 C5 109.7(3) . . ? C7 C4 C6 109.9(3) . . ? C5 C4 C6 110.1(3) . . ? C7 C4 N1 107.1(3) . . ? C5 C4 N1 106.4(3) . . ? C6 C4 N1 113.5(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C10 C8 C9 110.1(3) . . ? C10 C8 N2 108.5(3) . . ? C9 C8 N2 107.7(2) . . ? C10 C8 C11 109.3(3) . . ? C9 C8 C11 111.6(3) . . ? N2 C8 C11 109.7(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N4 C12 H12A 120.0 . . ? N4 C12 H12B 120.0 . . ? H12A C12 H12B 120.0 . . ? C13 N5 C14 107.5(3) . . ? C13 N5 C15 130.6(3) . . ? C14 N5 C15 121.8(3) . . ? C13 N6 C16 108.1(3) . . ? C13 N6 C20 126.2(2) . . ? C16 N6 C20 125.3(2) . . ? C13 N7 N8 114.9(3) . . ? C13 N7 H7 127(3) . . ? N8 N7 H7 118(3) . . ? C24 N8 N7 116.6(3) . . ? N6 C13 N5 108.4(2) . . ? N6 C13 N7 126.6(3) . . ? N5 C13 N7 125.0(3) . . ? C16 C14 N5 108.4(3) . . ? C16 C14 H14 125.8 . . ? N5 C14 H14 125.8 . . ? N5 C15 C18 106.4(3) . . ? N5 C15 C17 112.9(3) . . ? C18 C15 C17 112.8(4) . . ? N5 C15 C19 106.5(3) . . ? C18 C15 C19 110.5(4) . . ? C17 C15 C19 107.4(4) . . ? C14 C16 N6 107.6(3) . . ? C14 C16 H16 126.2 . . ? N6 C16 H16 126.2 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C15 C19 H19A 109.5 . . ? C15 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C15 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N6 C20 C21 107.0(3) . . ? N6 C20 C22 110.4(3) . . ? C21 C20 C22 112.0(3) . . ? N6 C20 C23 108.0(3) . . ? C21 C20 C23 110.0(3) . . ? C22 C20 C23 109.3(3) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N8 C24 H24A 120.0 . . ? N8 C24 H24B 120.0 . . ? H24A C24 H24B 120.0 . . ? H1A O1 H1B 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 N1 C1 1.345(4) . ? N1 C3 1.377(4) . ? N1 C4 1.523(4) . ? N2 C1 1.352(4) . ? N2 C2 1.377(4) . ? N2 C8 1.519(4) . ? N3 C1 1.370(4) . ? N3 N4 1.380(4) . ? N3 H3 0.83(4) . ? N4 C12 1.255(5) . ? C2 C3 1.344(4) . ? C2 H2 0.9500 . ? C3 H3A 0.9500 . ? C4 C7 1.514(5) . ? C4 C5 1.519(5) . ? C4 C6 1.519(5) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C10 1.515(5) . ? C8 C9 1.519(4) . ? C8 C11 1.520(5) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9500 . ? C12 H12B 0.9500 . ? N5 C13 1.351(4) . ? N5 C14 1.377(4) . ? N5 C15 1.508(4) . ? N6 C13 1.347(4) . ? N6 C16 1.379(4) . ? N6 C20 1.517(4) . ? N7 C13 1.365(4) . ? N7 N8 1.375(4) . ? N7 H7 0.87(5) . ? N8 C24 1.260(4) . ? C14 C16 1.335(5) . ? C14 H14 0.9500 . ? C15 C18 1.509(6) . ? C15 C17 1.511(6) . ? C15 C19 1.512(6) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.520(4) . ? C20 C22 1.525(5) . ? C20 C23 1.526(5) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9500 . ? C24 H24B 0.9500 . ? O1 H1A 0.8701 . ? O1 H1B 0.8699 . ? 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 C1 N3 N4 C12 178.8(4) . . . . ? C3 N1 C1 N2 0.5(3) . . . . ? C4 N1 C1 N2 -174.3(3) . . . . ? C3 N1 C1 N3 -176.3(3) . . . . ? C4 N1 C1 N3 9.0(5) . . . . ? C2 N2 C1 N1 0.1(3) . . . . ? C8 N2 C1 N1 173.5(2) . . . . ? C2 N2 C1 N3 176.9(3) . . . . ? C8 N2 C1 N3 -9.8(4) . . . . ? N4 N3 C1 N1 80.8(4) . . . . ? N4 N3 C1 N2 -95.4(4) . . . . ? C1 N2 C2 C3 -0.7(3) . . . . ? C8 N2 C2 C3 -174.3(3) . . . . ? N2 C2 C3 N1 1.0(3) . . . . ? C1 N1 C3 C2 -0.9(3) . . . . ? C4 N1 C3 C2 174.5(3) . . . . ? C1 N1 C4 C7 -125.4(3) . . . . ? C3 N1 C4 C7 60.3(4) . . . . ? C1 N1 C4 C5 117.3(3) . . . . ? C3 N1 C4 C5 -56.9(4) . . . . ? C1 N1 C4 C6 -3.9(5) . . . . ? C3 N1 C4 C6 -178.2(3) . . . . ? C1 N2 C8 C10 173.0(3) . . . . ? C2 N2 C8 C10 -14.6(4) . . . . ? C1 N2 C8 C9 -67.9(4) . . . . ? C2 N2 C8 C9 104.5(3) . . . . ? C1 N2 C8 C11 53.7(4) . . . . ? C2 N2 C8 C11 -133.9(3) . . . . ? C13 N7 N8 C24 179.0(3) . . . . ? C16 N6 C13 N5 0.5(3) . . . . ? C20 N6 C13 N5 -172.9(3) . . . . ? C16 N6 C13 N7 -175.9(3) . . . . ? C20 N6 C13 N7 10.7(5) . . . . ? C14 N5 C13 N6 -1.4(3) . . . . ? C15 N5 C13 N6 -178.9(3) . . . . ? C14 N5 C13 N7 175.1(3) . . . . ? C15 N5 C13 N7 -2.3(5) . . . . ? N8 N7 C13 N6 95.8(4) . . . . ? N8 N7 C13 N5 -80.0(4) . . . . ? C13 N5 C14 C16 1.9(4) . . . . ? C15 N5 C14 C16 179.5(3) . . . . ? C13 N5 C15 C18 108.6(4) . . . . ? C14 N5 C15 C18 -68.4(5) . . . . ? C13 N5 C15 C17 -15.7(5) . . . . ? C14 N5 C15 C17 167.2(4) . . . . ? C13 N5 C15 C19 -133.4(4) . . . . ? C14 N5 C15 C19 49.5(4) . . . . ? N5 C14 C16 N6 -1.5(4) . . . . ? C13 N6 C16 C14 0.6(3) . . . . ? C20 N6 C16 C14 174.1(3) . . . . ? C13 N6 C20 C21 69.8(4) . . . . ? C16 N6 C20 C21 -102.5(3) . . . . ? C13 N6 C20 C22 -52.3(4) . . . . ? C16 N6 C20 C22 135.4(3) . . . . ? C13 N6 C20 C23 -171.8(3) . . . . ? C16 N6 C20 C23 15.9(4) . . . . ?