#------------------------------------------------------------------------------ #$Date: 2018-01-10 07:45:33 +0200 (Wed, 10 Jan 2018) $ #$Revision: 205019 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229932.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_7229932 loop_ _publ_author_name 'Yang, Wei' 'Lu, Huanchang' 'Liao, Longyu' 'Fan, Guijuan' 'Ma, Qing' 'Huang, Jinglun' _publ_section_title ; Synthesis, and single crystal structure of fully-substituted polynitrobenzene derivatives for high-energy materials ; _journal_issue 4 _journal_name_full 'RSC Advances' _journal_page_first 2203 _journal_paper_doi 10.1039/C7RA13346D _journal_volume 8 _journal_year 2018 _chemical_formula_sum 'C8 H2 Cl3 N5 O4' _chemical_formula_weight 338.50 _chemical_name_systematic ; ? ; _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' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2017-05-25 deposited with the CCDC. 2018-01-03 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.832(4) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 8.8432(19) _cell_length_b 17.400(4) _cell_length_c 16.430(4) _cell_measurement_reflns_used 4096 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 56.497 _cell_measurement_theta_min 4.677 _cell_volume 2526.8(10) _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-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 0.0357 _diffrn_reflns_av_unetI/netI 0.0368 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 14977 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.999 _diffrn_reflns_theta_min 1.705 _exptl_absorpt_coefficient_mu 0.746 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6378 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.780 _exptl_crystal_description prismatic _exptl_crystal_F_000 1344 _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.130 _refine_diff_density_max 0.327 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.058 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 361 _refine_ls_number_reflns 4970 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0413 _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^)+(0.0539P)^2^+0.7201P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1040 _refine_ls_wR_factor_ref 0.1139 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3636 _reflns_number_total 4970 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ra13346d2.cif _cod_data_source_block cd15349m _cod_original_cell_volume 2526.9(9) _cod_database_code 7229932 _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 0.859 _shelx_estimated_absorpt_t_max 0.909 _shelxl_version_number 2013-4 _shelx_res_file ; TITL cd15349m in P2(1)/n CELL 0.71073 8.8432 17.4001 16.4302 90.000 91.832 90.000 ZERR 8.00 0.0019 0.0037 0.0036 0.000 0.004 0.000 LATT 1 SYMM -x+1/2, y+1/2, -z+1/2 SFAC C H N O Cl UNIT 64 16 40 32 24 OMIT -3.00 52.00 L.S. 10 ACTA BOND $H FMAP 2 PLAN 0 wpdb -1 size 0.21 0.16 0.13 mpla n6 n7 n8 c15 c16 mpla c9 > c14 mpla n1 n2 n3 c7 c8 mpla c1 > c6 htab conf EQIV $1 -x+1, -y+1, -z HTAB C7 O2_$1 EQIV $2 x+1/2, -y+1/2, z-1/2 HTAB C8 O1_$2 EQIV $3 -x+1, -y, -z HTAB C15 O6_$3 EQIV $4 x-1/2, -y+1/2, z+1/2 HTAB C16 O8_$4 BIND O1 N7 TEMP 0.000 WGHT 0.053900 0.720100 FVAR 0.09357 CL1 5 1.019610 0.360919 -0.024988 11.00000 0.03843 0.10998 = 0.05364 -0.01034 0.00849 0.00281 CL2 5 0.418902 0.356214 -0.082089 11.00000 0.04324 0.09066 = 0.04407 -0.00570 -0.00848 -0.00342 CL3 5 0.643538 0.438459 0.211636 11.00000 0.06683 0.08274 = 0.03532 -0.01394 0.00763 -0.00303 CL4 5 0.764423 0.063718 -0.183364 11.00000 0.07120 0.09454 = 0.03484 -0.01599 0.00606 0.01025 CL5 5 0.402905 0.143938 0.057113 11.00000 0.03896 0.11178 = 0.05250 -0.01238 0.00781 0.00832 CL6 5 1.004781 0.149539 0.107014 11.00000 0.04249 0.09679 = 0.05045 -0.00870 -0.01004 -0.00544 N1 3 0.739703 0.337744 -0.126315 11.00000 0.04906 0.04601 = 0.02953 -0.00176 0.00298 -0.00009 N2 3 0.730546 0.263735 -0.149071 11.00000 0.11580 0.04876 = 0.04357 -0.00776 0.00388 -0.00164 N3 3 0.759232 0.340165 -0.257049 11.00000 0.07349 0.08215 = 0.03227 -0.00397 0.00471 0.00225 N4 3 0.397327 0.404315 0.090520 11.00000 0.04035 0.07252 = 0.04711 -0.00018 0.00656 -0.00036 N5 3 0.947029 0.412479 0.142664 11.00000 0.04580 0.08345 = 0.04146 -0.00587 -0.00172 -0.00903 N6 3 0.686978 0.166378 0.155140 11.00000 0.04815 0.04362 = 0.03017 -0.00320 0.00116 0.00057 N7 3 0.688490 0.240803 0.177531 11.00000 0.10393 0.04850 = 0.04357 -0.00524 0.00529 -0.00171 N8 3 0.672196 0.164480 0.286252 11.00000 0.07335 0.07290 = 0.03242 -0.00355 -0.00014 -0.00524 N9 3 0.468199 0.090894 -0.110404 11.00000 0.04457 0.07576 = 0.03781 -0.00360 -0.00281 0.00030 N10 3 1.019358 0.101912 -0.067425 11.00000 0.04352 0.08685 = 0.04778 0.00593 0.00915 0.00438 O1 4 0.337129 0.348969 0.117232 11.00000 0.06035 0.11523 = 0.11428 0.04445 0.03219 -0.00243 O2 4 0.341261 0.466315 0.083545 11.00000 0.06731 0.07618 = 0.16495 -0.00652 0.03145 0.02472 O3 4 1.006580 0.356711 0.172524 11.00000 0.06347 0.12073 = 0.07524 0.01925 -0.02651 0.00461 O4 4 0.982312 0.477407 0.154779 11.00000 0.09176 0.09466 = 0.12054 -0.02627 -0.03344 -0.02726 O5 4 0.416596 0.144757 -0.146795 11.00000 0.06488 0.11952 = 0.07613 0.02839 -0.02773 -0.00115 O6 4 0.420363 0.026470 -0.113791 11.00000 0.08358 0.08179 = 0.10293 -0.01995 -0.02948 -0.02037 O7 4 1.067302 0.039108 -0.077875 11.00000 0.07928 0.10593 = 0.14254 0.00016 0.04659 0.03787 O8 4 1.084873 0.160337 -0.081744 11.00000 0.06301 0.12115 = 0.10850 0.02315 0.03242 -0.01130 C1 1 0.840662 0.373809 0.007775 11.00000 0.03618 0.04781 = 0.03672 0.00137 0.00397 -0.00027 C2 1 0.717940 0.359959 -0.044444 11.00000 0.04338 0.04223 = 0.02800 0.00151 0.00133 -0.00053 C3 1 0.571788 0.370152 -0.017658 11.00000 0.03835 0.04705 = 0.03678 0.00133 -0.00305 -0.00296 C4 1 0.551909 0.394379 0.061142 11.00000 0.03820 0.04586 = 0.03511 0.00349 0.00558 0.00042 C5 1 0.672675 0.409502 0.113930 11.00000 0.04550 0.04455 = 0.02978 0.00020 0.00386 -0.00276 C6 1 0.816353 0.398537 0.086064 11.00000 0.03810 0.04944 = 0.03424 0.00006 -0.00417 -0.00368 C7 1 0.756502 0.381114 -0.191579 11.00000 0.09049 0.05672 = 0.03792 0.00267 0.01092 -0.00452 AFIX 43 H7 2 0.765239 0.434369 -0.190427 11.00000 -1.20000 AFIX 0 C8 1 0.743741 0.269214 -0.227715 11.00000 0.09743 0.06844 = 0.04373 -0.01876 0.00064 0.00485 AFIX 43 H8 2 0.742425 0.226203 -0.261334 11.00000 -1.20000 AFIX 0 C9 1 0.743055 0.093926 -0.085558 11.00000 0.04718 0.04781 = 0.02894 0.00026 0.00343 0.00544 C10 1 0.601305 0.105264 -0.055967 11.00000 0.04168 0.04678 = 0.03187 0.00116 -0.00408 0.00086 C11 1 0.580560 0.131002 0.022017 11.00000 0.03691 0.04894 = 0.03600 0.00118 0.00375 0.00350 C12 1 0.706299 0.144141 0.073136 11.00000 0.04264 0.04133 = 0.02859 0.00005 0.00002 0.00306 C13 1 0.849686 0.134345 0.043828 11.00000 0.03903 0.04936 = 0.03506 0.00156 -0.00344 0.00037 C14 1 0.866388 0.109603 -0.035243 11.00000 0.03526 0.05267 = 0.03888 0.00448 0.00291 0.00573 C15 1 0.675985 0.122780 0.221021 11.00000 0.08842 0.05435 = 0.03495 0.00397 -0.00151 -0.00297 AFIX 43 H15 2 0.671587 0.069381 0.220417 11.00000 -1.20000 AFIX 0 C16 1 0.679551 0.235041 0.256649 11.00000 0.08723 0.06384 = 0.04337 -0.01740 -0.00025 -0.00038 AFIX 43 H16 2 0.678433 0.278100 0.290157 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM cd15349m in P2(1)/n REM R1 = 0.0413 for 3636 Fo > 4sig(Fo) and 0.0582 for all 4970 data REM 361 parameters refined using 0 restraints END WGHT 0.0539 0.7197 REM Instructions for potential hydrogen bonds HTAB C7 O2_$1 HTAB C8 O1_$2 HTAB C15 O6_$3 HTAB C16 O8_$4 REM Highest difference peak 0.327, deepest hole -0.236, 1-sigma level 0.058 Q1 1 1.0293 0.1367 -0.1238 11.00000 0.05 0.33 Q2 1 0.7350 0.3520 -0.0837 11.00000 0.05 0.25 Q3 1 0.3869 0.3757 0.1556 11.00000 0.05 0.25 Q4 1 1.1118 0.0477 -0.0205 11.00000 0.05 0.24 Q5 1 0.7681 0.3597 -0.0154 11.00000 0.05 0.23 Q6 1 0.9916 0.3605 -0.0715 11.00000 0.05 0.22 Q7 1 1.0173 0.4862 0.0950 11.00000 0.05 0.21 Q8 1 0.5695 0.3579 0.0437 11.00000 0.05 0.20 Q9 1 0.4643 0.3168 -0.0592 11.00000 0.05 0.20 Q10 1 0.7485 0.0852 -0.1255 11.00000 0.05 0.19 Q11 1 0.4976 0.1795 -0.1394 11.00000 0.05 0.19 Q12 1 0.6959 0.1497 0.1158 11.00000 0.05 0.19 Q13 1 0.9413 0.3179 0.1553 11.00000 0.05 0.18 Q14 1 0.3225 0.3239 0.1210 11.00000 0.05 0.18 Q15 1 0.7246 0.2789 0.1568 11.00000 0.05 0.18 Q16 1 0.6525 0.1164 0.0599 11.00000 0.05 0.18 Q17 1 1.1102 0.1442 0.0627 11.00000 0.05 0.18 Q18 1 0.8178 0.4034 0.0452 11.00000 0.05 0.18 Q19 1 0.6334 0.1414 0.0422 11.00000 0.05 0.18 Q20 1 0.7048 0.2307 -0.1233 11.00000 0.05 0.18 ; _shelx_res_checksum 63109 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 Cl1 Cl 1.01961(7) 0.36092(5) -0.02499(4) 0.0672(2) Uani 1 1 d . . Cl2 Cl 0.41890(7) 0.35621(4) -0.08209(4) 0.0595(2) Uani 1 1 d . . Cl3 Cl 0.64354(8) 0.43846(4) 0.21164(4) 0.0615(2) Uani 1 1 d . . Cl4 Cl 0.76442(8) 0.06372(4) -0.18336(4) 0.0668(2) Uani 1 1 d . . Cl5 Cl 0.40291(7) 0.14394(5) 0.05711(4) 0.0676(2) Uani 1 1 d . . Cl6 Cl 1.00478(7) 0.14954(4) 0.10701(4) 0.0635(2) Uani 1 1 d . . N1 N 0.7397(2) 0.33774(10) -0.12632(11) 0.0415(4) Uani 1 1 d . . N2 N 0.7305(3) 0.26374(12) -0.14907(14) 0.0693(7) Uani 1 1 d . . N3 N 0.7592(3) 0.34016(14) -0.25705(13) 0.0626(6) Uani 1 1 d . . N4 N 0.3973(2) 0.40432(14) 0.09052(13) 0.0532(5) Uani 1 1 d . . N5 N 0.9470(2) 0.41248(15) 0.14266(13) 0.0570(6) Uani 1 1 d . . N6 N 0.6870(2) 0.16638(10) 0.15514(11) 0.0407(4) Uani 1 1 d . . N7 N 0.6885(3) 0.24080(12) 0.17753(13) 0.0653(6) Uani 1 1 d . . N8 N 0.6722(3) 0.16448(14) 0.28625(12) 0.0596(6) Uani 1 1 d . . N9 N 0.4682(2) 0.09089(14) -0.11040(12) 0.0528(5) Uani 1 1 d . . N10 N 1.0194(2) 0.10191(16) -0.06742(13) 0.0592(6) Uani 1 1 d . . O1 O 0.3371(2) 0.34897(14) 0.11723(16) 0.0960(8) Uani 1 1 d . . O2 O 0.3413(2) 0.46632(13) 0.08354(19) 0.1022(9) Uani 1 1 d . . O3 O 1.0066(2) 0.35671(15) 0.17252(14) 0.0871(7) Uani 1 1 d . . O4 O 0.9823(3) 0.47741(15) 0.15478(17) 0.1031(8) Uani 1 1 d . . O5 O 0.4166(2) 0.14476(14) -0.14679(14) 0.0875(7) Uani 1 1 d . . O6 O 0.4204(3) 0.02647(13) -0.11379(15) 0.0901(7) Uani 1 1 d . . O7 O 1.0673(3) 0.03911(15) -0.07787(18) 0.1083(9) Uani 1 1 d . . O8 O 1.0849(3) 0.16034(15) -0.08174(17) 0.0969(8) Uani 1 1 d . . C1 C 0.8407(2) 0.37381(13) 0.00777(13) 0.0402(5) Uani 1 1 d . . C2 C 0.7179(2) 0.35996(12) -0.04444(13) 0.0379(5) Uani 1 1 d . . C3 C 0.5718(2) 0.37015(12) -0.01766(14) 0.0408(5) Uani 1 1 d . . C4 C 0.5519(2) 0.39438(13) 0.06114(13) 0.0396(5) Uani 1 1 d . . C5 C 0.6727(2) 0.40950(12) 0.11393(13) 0.0399(5) Uani 1 1 d . . C6 C 0.8164(2) 0.39854(13) 0.08606(13) 0.0407(5) Uani 1 1 d . . C7 C 0.7565(3) 0.38111(16) -0.19158(15) 0.0615(7) Uani 1 1 d . . H7 H 0.7652 0.4344 -0.1904 0.074 Uiso 1 1 calc R U C8 C 0.7437(4) 0.26921(18) -0.22772(17) 0.0699(8) Uani 1 1 d . . H8 H 0.7424 0.2262 -0.2613 0.084 Uiso 1 1 calc R U C9 C 0.7431(3) 0.09393(13) -0.08556(13) 0.0413(5) Uani 1 1 d . . C10 C 0.6013(2) 0.10526(12) -0.05597(13) 0.0402(5) Uani 1 1 d . . C11 C 0.5806(2) 0.13100(13) 0.02202(13) 0.0406(5) Uani 1 1 d . . C12 C 0.7063(2) 0.14414(12) 0.07314(13) 0.0375(5) Uani 1 1 d . . C13 C 0.8497(2) 0.13435(13) 0.04383(13) 0.0412(5) Uani 1 1 d . . C14 C 0.8664(2) 0.10960(13) -0.03524(13) 0.0422(5) Uani 1 1 d . . C15 C 0.6760(3) 0.12278(16) 0.22102(15) 0.0593(7) Uani 1 1 d . . H15 H 0.6716 0.0694 0.2204 0.071 Uiso 1 1 calc R U C16 C 0.6796(3) 0.23504(17) 0.25665(16) 0.0649(7) Uani 1 1 d . . H16 H 0.6784 0.2781 0.2902 0.078 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 Cl1 0.0384(3) 0.1100(6) 0.0536(4) -0.0103(4) 0.0085(3) 0.0028(3) Cl2 0.0432(3) 0.0907(5) 0.0441(4) -0.0057(3) -0.0085(3) -0.0034(3) Cl3 0.0668(4) 0.0827(5) 0.0353(3) -0.0139(3) 0.0076(3) -0.0030(3) Cl4 0.0712(4) 0.0945(5) 0.0348(3) -0.0160(3) 0.0061(3) 0.0102(4) Cl5 0.0390(3) 0.1118(6) 0.0525(4) -0.0124(4) 0.0078(3) 0.0083(3) Cl6 0.0425(3) 0.0968(5) 0.0505(4) -0.0087(3) -0.0100(3) -0.0054(3) N1 0.0491(11) 0.0460(11) 0.0295(10) -0.0018(8) 0.0030(8) -0.0001(8) N2 0.116(2) 0.0488(13) 0.0436(13) -0.0078(10) 0.0039(12) -0.0016(12) N3 0.0735(15) 0.0821(17) 0.0323(12) -0.0040(11) 0.0047(10) 0.0023(12) N4 0.0403(11) 0.0725(15) 0.0471(13) -0.0002(11) 0.0066(9) -0.0004(11) N5 0.0458(12) 0.0834(17) 0.0415(12) -0.0059(11) -0.0017(9) -0.0090(12) N6 0.0482(11) 0.0436(11) 0.0302(10) -0.0032(8) 0.0012(8) 0.0006(8) N7 0.1039(19) 0.0485(13) 0.0436(13) -0.0052(10) 0.0053(12) -0.0017(12) N8 0.0734(15) 0.0729(15) 0.0324(11) -0.0035(10) -0.0001(10) -0.0052(11) N9 0.0446(11) 0.0758(16) 0.0378(12) -0.0036(11) -0.0028(9) 0.0003(11) N10 0.0435(12) 0.0869(18) 0.0478(13) 0.0059(12) 0.0092(10) 0.0044(12) O1 0.0603(13) 0.1152(19) 0.114(2) 0.0445(15) 0.0322(13) -0.0024(12) O2 0.0673(14) 0.0762(15) 0.165(3) -0.0065(15) 0.0315(15) 0.0247(12) O3 0.0635(13) 0.1207(19) 0.0752(15) 0.0192(13) -0.0265(11) 0.0046(12) O4 0.0918(17) 0.0947(17) 0.121(2) -0.0263(15) -0.0334(15) -0.0273(14) O5 0.0649(13) 0.1195(19) 0.0761(15) 0.0284(13) -0.0277(11) -0.0012(12) O6 0.0836(15) 0.0818(16) 0.1029(19) -0.0199(13) -0.0295(13) -0.0204(12) O7 0.0793(16) 0.1059(19) 0.143(3) 0.0002(17) 0.0466(16) 0.0379(14) O8 0.0630(14) 0.121(2) 0.109(2) 0.0232(16) 0.0324(13) -0.0113(13) C1 0.0362(11) 0.0478(13) 0.0367(12) 0.0014(10) 0.0040(9) -0.0003(9) C2 0.0434(12) 0.0422(12) 0.0280(11) 0.0015(9) 0.0013(9) -0.0005(9) C3 0.0384(12) 0.0471(13) 0.0368(12) 0.0013(10) -0.0031(9) -0.0030(9) C4 0.0382(11) 0.0459(13) 0.0351(12) 0.0035(10) 0.0056(9) 0.0004(9) C5 0.0455(12) 0.0445(13) 0.0298(11) 0.0002(9) 0.0039(9) -0.0028(9) C6 0.0381(11) 0.0494(13) 0.0342(12) 0.0001(10) -0.0042(9) -0.0037(10) C7 0.090(2) 0.0567(16) 0.0379(14) 0.0027(12) 0.0109(13) -0.0045(14) C8 0.097(2) 0.0684(19) 0.0437(16) -0.0188(14) 0.0006(15) 0.0049(16) C9 0.0472(13) 0.0478(13) 0.0289(11) 0.0003(9) 0.0034(9) 0.0054(10) C10 0.0417(12) 0.0468(13) 0.0319(12) 0.0012(9) -0.0041(9) 0.0009(10) C11 0.0369(11) 0.0489(13) 0.0360(12) 0.0012(10) 0.0038(9) 0.0035(9) C12 0.0426(12) 0.0413(12) 0.0286(11) 0.0000(9) 0.0000(9) 0.0031(9) C13 0.0390(12) 0.0494(13) 0.0351(12) 0.0016(10) -0.0034(9) 0.0004(9) C14 0.0353(11) 0.0527(14) 0.0389(13) 0.0045(10) 0.0029(9) 0.0057(9) C15 0.088(2) 0.0543(15) 0.0350(14) 0.0040(11) -0.0015(13) -0.0030(13) C16 0.087(2) 0.0638(18) 0.0434(15) -0.0174(13) -0.0002(14) -0.0004(14) 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' Cl Cl 0.1484 0.1585 '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 C7 N1 N2 109.2(2) C7 N1 C2 129.4(2) N2 N1 C2 121.10(18) C8 N2 N1 101.5(2) C7 N3 C8 101.8(2) O1 N4 O2 125.3(2) O1 N4 C4 117.1(2) O2 N4 C4 117.5(2) O4 N5 O3 126.2(2) O4 N5 C6 117.2(2) O3 N5 C6 116.6(2) C15 N6 N7 109.1(2) C15 N6 C12 129.3(2) N7 N6 C12 121.46(18) C16 N7 N6 101.4(2) C16 N7 O1 103.04(19) N6 N7 O1 114.26(16) C15 N8 C16 102.3(2) O5 N9 O6 125.6(2) O5 N9 C10 117.0(2) O6 N9 C10 117.4(2) O7 N10 O8 125.2(2) O7 N10 C14 118.1(2) O8 N10 C14 116.7(2) N4 O1 N7 97.31(16) C6 C1 C2 119.35(19) C6 C1 Cl1 120.66(17) C2 C1 Cl1 119.99(17) C1 C2 C3 120.0(2) C1 C2 N1 120.54(19) C3 C2 N1 119.39(19) C4 C3 C2 119.0(2) C4 C3 Cl2 120.24(17) C2 C3 Cl2 120.76(17) C3 C4 C5 121.98(19) C3 C4 N4 119.40(19) C5 C4 N4 118.6(2) C6 C5 C4 117.9(2) C6 C5 Cl3 121.41(17) C4 C5 Cl3 120.64(17) C5 C6 C1 121.7(2) C5 C6 N5 118.6(2) C1 C6 N5 119.68(19) N3 C7 N1 111.5(2) N3 C7 C8 39.85(15) N1 C7 C8 71.62(16) N3 C7 H7 124.3 N1 C7 H7 124.3 C8 C7 H7 164.1 N2 C8 N3 116.0(2) N2 C8 C7 77.71(17) N3 C8 C7 38.33(14) N2 C8 H8 122.0 N3 C8 H8 122.0 C7 C8 H8 160.3 C10 C9 C14 118.3(2) C10 C9 Cl4 120.49(17) C14 C9 Cl4 121.18(17) C9 C10 C11 121.8(2) C9 C10 N9 118.7(2) C11 C10 N9 119.47(19) C10 C11 C12 119.23(19) C10 C11 Cl5 120.65(17) C12 C11 Cl5 120.09(17) C13 C12 C11 119.6(2) C13 C12 N6 120.33(19) C11 C12 N6 120.04(19) C14 C13 C12 119.6(2) C14 C13 Cl6 120.68(17) C12 C13 Cl6 119.71(17) C9 C14 C13 121.4(2) C9 C14 N10 119.1(2) C13 C14 N10 119.5(2) N8 C15 N6 111.0(2) N8 C15 C16 39.34(15) N6 C15 C16 71.69(16) N8 C15 H15 124.5 N6 C15 H15 124.5 C16 C15 H15 163.8 N7 C16 N8 116.2(2) N7 C16 C15 77.83(17) N8 C16 C15 38.38(13) N7 C16 H16 121.9 N8 C16 H16 121.9 C15 C16 H16 160.3 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C1 1.703(2) Cl2 C3 1.708(2) Cl3 C5 1.710(2) Cl4 C9 1.707(2) Cl5 C11 1.706(2) Cl6 C13 1.714(2) N1 C7 1.323(3) N1 N2 1.343(3) N1 C2 1.419(3) N2 C8 1.305(3) N3 C7 1.291(3) N3 C8 1.334(4) N4 O1 1.191(3) N4 O2 1.191(3) N4 C4 1.474(3) N5 O4 1.187(3) N5 O3 1.201(3) N5 C6 1.480(3) N6 C15 1.328(3) N6 N7 1.346(3) N6 C12 1.417(3) N7 C16 1.309(3) N7 O1 3.739(4) N8 C15 1.296(3) N8 C16 1.323(3) N9 O5 1.194(3) N9 O6 1.199(3) N9 C10 1.477(3) N10 O7 1.187(3) N10 O8 1.197(3) N10 C14 1.474(3) C1 C6 1.380(3) C1 C2 1.383(3) C2 C3 1.390(3) C3 C4 1.378(3) C4 C5 1.379(3) C5 C6 1.378(3) C7 C8 2.038(4) C7 H7 0.9300 C8 H8 0.9300 C9 C10 1.373(3) C9 C14 1.375(3) C10 C11 1.375(3) C11 C12 1.391(3) C12 C13 1.381(3) C13 C14 1.381(3) C15 C16 2.039(4) C15 H15 0.9300 C16 H16 0.9300 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 C7 H7 O2 0.93 2.66 3.323(4) 129.1 3_665 C8 H8 O1 0.93 2.55 3.396(4) 151.6 4_665 C15 H15 O6 0.93 2.53 3.237(3) 132.6 3_655 C16 H16 O8 0.93 2.52 3.348(4) 147.7 4_566 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 C7 N1 N2 C8 0.3(3) C2 N1 N2 C8 174.7(2) C15 N6 N7 C16 0.6(3) C12 N6 N7 C16 -175.2(2) C15 N6 N7 O1 -109.48(19) C12 N6 N7 O1 74.8(2) O2 N4 O1 N7 -157.5(3) C4 N4 O1 N7 24.8(2) C6 C1 C2 C3 -0.7(3) Cl1 C1 C2 C3 179.73(17) C6 C1 C2 N1 177.2(2) Cl1 C1 C2 N1 -2.3(3) C7 N1 C2 C1 -87.8(3) N2 N1 C2 C1 99.1(3) C7 N1 C2 C3 90.1(3) N2 N1 C2 C3 -83.0(3) C1 C2 C3 C4 0.2(3) N1 C2 C3 C4 -177.7(2) C1 C2 C3 Cl2 177.97(17) N1 C2 C3 Cl2 0.0(3) C2 C3 C4 C5 0.6(3) Cl2 C3 C4 C5 -177.12(17) C2 C3 C4 N4 -179.1(2) Cl2 C3 C4 N4 3.1(3) O1 N4 C4 C3 86.1(3) O2 N4 C4 C3 -91.9(3) O1 N4 C4 C5 -93.7(3) O2 N4 C4 C5 88.4(3) C3 C4 C5 C6 -1.0(3) N4 C4 C5 C6 178.8(2) C3 C4 C5 Cl3 -179.28(18) N4 C4 C5 Cl3 0.5(3) C4 C5 C6 C1 0.5(3) Cl3 C5 C6 C1 178.78(18) C4 C5 C6 N5 -178.4(2) Cl3 C5 C6 N5 -0.1(3) C2 C1 C6 C5 0.3(3) Cl1 C1 C6 C5 179.89(18) C2 C1 C6 N5 179.2(2) Cl1 C1 C6 N5 -1.3(3) O4 N5 C6 C5 -77.7(3) O3 N5 C6 C5 101.7(3) O4 N5 C6 C1 103.4(3) O3 N5 C6 C1 -77.2(3) C8 N3 C7 N1 -0.3(3) N2 N1 C7 N3 0.0(3) C2 N1 C7 N3 -173.8(2) N2 N1 C7 C8 -0.2(2) C2 N1 C7 C8 -174.0(2) N1 N2 C8 N3 -0.5(4) N1 N2 C8 C7 -0.20(19) C7 N3 C8 N2 0.5(4) C14 C9 C10 C11 -0.5(3) Cl4 C9 C10 C11 -178.71(18) C14 C9 C10 N9 178.1(2) Cl4 C9 C10 N9 -0.1(3) O5 N9 C10 C9 -94.1(3) O6 N9 C10 C9 86.6(3) O5 N9 C10 C11 84.6(3) O6 N9 C10 C11 -94.8(3) C9 C10 C11 C12 -1.6(3) N9 C10 C11 C12 179.7(2) C9 C10 C11 Cl5 -179.60(18) N9 C10 C11 Cl5 1.8(3) C10 C11 C12 C13 2.8(3) Cl5 C11 C12 C13 -179.26(17) C10 C11 C12 N6 -176.3(2) Cl5 C11 C12 N6 1.6(3) C15 N6 C12 C13 -88.8(3) N7 N6 C12 C13 86.0(3) C15 N6 C12 C11 90.3(3) N7 N6 C12 C11 -94.9(3) C11 C12 C13 C14 -1.7(3) N6 C12 C13 C14 177.3(2) C11 C12 C13 Cl6 -179.33(17) N6 C12 C13 Cl6 -0.2(3) C10 C9 C14 C13 1.6(3) Cl4 C9 C14 C13 179.74(18) C10 C9 C14 N10 -176.6(2) Cl4 C9 C14 N10 1.5(3) C12 C13 C14 C9 -0.4(3) Cl6 C13 C14 C9 177.11(18) C12 C13 C14 N10 177.8(2) Cl6 C13 C14 N10 -4.7(3) O7 N10 C14 C9 -73.5(3) O8 N10 C14 C9 105.7(3) O7 N10 C14 C13 108.2(3) O8 N10 C14 C13 -72.5(3) C16 N8 C15 N6 0.7(3) N7 N6 C15 N8 -0.9(3) C12 N6 C15 N8 174.5(2) N7 N6 C15 C16 -0.40(19) C12 N6 C15 C16 174.9(2) N6 N7 C16 N8 -0.2(3) O1 N7 C16 N8 118.3(2) N6 N7 C16 C15 -0.38(18) O1 N7 C16 C15 118.10(13) C15 N8 C16 N7 -0.3(4)