#------------------------------------------------------------------------------ #$Date: 2018-02-18 11:45:15 +0200 (Sun, 18 Feb 2018) $ #$Revision: 206489 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229933.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_7229933 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 'C10 H4 Cl2 N8 O4' _chemical_formula_weight 371.11 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 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 92.886(4) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 16.424(3) _cell_length_b 10.270(2) _cell_length_c 17.559(3) _cell_measurement_reflns_used 3437 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 49.276 _cell_measurement_theta_min 4.645 _cell_volume 2958.0(9) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.963 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_unetI/netI 0.0514 _diffrn_reflns_Laue_measured_fraction_full 0.963 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 15478 _diffrn_reflns_point_group_measured_fraction_full 0.963 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 1.241 _exptl_absorpt_coefficient_mu 0.476 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6452 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.667 _exptl_crystal_description prismatic _exptl_crystal_F_000 1488 _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.130 _refine_diff_density_max 0.544 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.098 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 433 _refine_ls_number_reflns 5161 _refine_ls_number_restraints 13 _refine_ls_restrained_S_all 1.122 _refine_ls_R_factor_all 0.0965 _refine_ls_R_factor_gt 0.0788 _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^)+(0.0746P)^2^+9.2256P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2088 _refine_ls_wR_factor_ref 0.2193 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3958 _reflns_number_total 5161 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ra13346d2.cif _cod_data_source_block cd16192 _cod_depositor_comments ; 2018-02-08 Z value and formula fixed to values more according to usual chemical conventions. miguel ; _cod_original_formula_sum 'C20 H8 Cl4 N16 O8' _cod_original_formula_weight 742.22 _cod_original_formula_units_Z 4 _cod_original_cell_volume 2958.0(10) _cod_database_code 7229933 _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 0.902 _shelx_estimated_absorpt_t_max 0.941 _shelxl_version_number 2013-4 _shelx_res_file ; TITL cd16192 in P2(1)/c CELL 0.71073 16.4241 10.2699 17.5588 90.000 92.886 90.000 ZERR 4.00 0.0031 0.0021 0.0033 0.000 0.004 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O Cl UNIT 80 32 64 32 16 OMIT 1 3 8 OMIT 10 4 2 OMIT 2 2 14 OMIT -9 4 7 OMIT 9 6 1 OMIT -10 4 12 OMIT -10 2 9 OMIT 9 5 7 OMIT -9 2 8 OMIT 9 3 1 OMIT 9 3 7 OMIT 9 4 0 OMIT 1 2 13 OMIT 1 0 6 OMIT 1 0 10 OMIT 10 2 6 OMIT 1 1 9 OMIT -10 2 1 OMIT 9 1 4 OMIT -9 4 8 OMIT -9 2 3 OMIT -9 4 6 OMIT 9 1 0 OMIT -3.00 50.00 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 HTAB C17 N7_$4 HTAB C9 N7 HTAB C8 O6_$3 HTAB C7 O4_$2 HTAB C7 N15_$1 isor 0.01 c19 c20 dfix 2.10 0.02 c19 c20 HTAB C17 N7_$4 HTAB C9 N7 HTAB C8 O6_$3 HTAB C7 O4_$2 HTAB C7 N15_$1 wpdb -1 size 0.22 0.17 0.13 mpla n11 c12 c13 c19 c20 mpla c14 c15 c16 c17 c18 mpla c11 > c16 mpla n6 n7 n8 c7 c8 mpla n3 n4 n5 c9 c10 mpla c1 > c6 conf EQIV $1 x, -y+3/2, z-1/2 HTAB C7 N15_$1 EQIV $2 -x+2, -y+2, -z HTAB C7 O4_$2 EQIV $3 -x+1, -y+1, -z+1 HTAB C8 O6_$3 HTAB C9 N7 EQIV $4 x, -y+1/2, z+1/2 HTAB C17 N7_$4 HTAB C7 N15_$1 HTAB C7 O4_$2 HTAB C8 O6_$3 HTAB C9 N7 HTAB C17 N7_$4 WGHT 0.074600 9.225600 FVAR 0.07752 MOLE 1 CL1 5 0.868809 0.909444 0.271582 11.00000 0.07343 0.07753 = 0.04638 -0.01478 0.02273 0.00486 CL2 5 1.100094 0.690057 0.111531 11.00000 0.04630 0.07853 = 0.06080 0.02078 0.01213 0.03225 CL3 5 0.655421 0.054724 0.750115 11.00000 0.06536 0.08486 = 0.05006 0.02274 -0.01151 0.00215 CL4 5 0.418888 0.330821 0.605386 11.00000 0.04294 0.06219 = 0.06956 -0.01052 0.00293 0.01724 N1 3 1.023109 0.763785 0.253231 11.00000 0.05324 0.07093 = 0.03813 0.00868 -0.00083 0.00597 N2 3 0.999032 0.764255 -0.025797 11.00000 0.04320 0.05166 = 0.03917 -0.00278 0.00576 0.00567 N3 3 0.852119 0.908058 -0.021091 11.00000 0.03218 0.04811 = 0.04416 0.01718 -0.00056 -0.00534 N4 3 0.891272 0.958437 -0.080742 11.00000 0.04360 0.07214 = 0.04638 0.02208 0.00027 -0.00981 N5 3 0.758878 0.925570 -0.112568 11.00000 0.05008 0.17943 = 0.07032 0.05759 -0.02124 -0.02901 N6 3 0.789680 0.979565 0.121449 11.00000 0.03094 0.02894 = 0.06259 0.00405 0.01226 -0.00100 N7 3 0.720135 0.911646 0.131030 11.00000 0.03477 0.03913 = 0.11662 0.01096 0.02307 0.00006 N8 3 0.695288 1.123881 0.122686 11.00000 0.04782 0.04365 = 0.14488 0.02347 0.03353 0.01709 N9 3 0.504976 0.217998 0.741656 11.00000 0.04621 0.07633 = 0.04000 -0.00791 0.00674 -0.01160 N10 3 0.498105 0.257166 0.462340 11.00000 0.04528 0.06101 = 0.04226 0.00777 -0.00039 0.00133 N11 3 0.641216 0.105985 0.459404 11.00000 0.03789 0.04956 = 0.04705 -0.00820 0.01073 -0.00413 N12 3 0.635584 -0.010944 0.427208 11.00000 0.09138 0.07956 = 0.08039 -0.03844 0.04331 -0.03874 N13 3 0.715736 0.115626 0.360947 11.00000 0.06879 0.12787 = 0.06247 -0.02517 0.03027 -0.02489 N14 3 0.720122 0.020133 0.594352 11.00000 0.03507 0.02735 = 0.06521 0.00068 0.00212 0.00202 N15 3 0.785826 0.085419 0.570323 11.00000 0.03685 0.03675 = 0.11775 0.00565 0.00783 0.00149 N16 3 0.819350 -0.118887 0.603247 11.00000 0.05394 0.03746 = 0.17494 0.01479 0.01302 0.01739 O1 4 1.076793 0.834121 0.277533 11.00000 0.08436 0.16079 = 0.05522 0.01962 -0.02820 -0.03486 O2 4 1.003766 0.660835 0.278551 11.00000 0.11940 0.08139 = 0.05773 0.03119 0.00117 0.01133 O3 4 0.961915 0.675968 -0.056756 11.00000 0.08862 0.07246 = 0.05610 -0.02438 0.01520 -0.00949 O4 4 1.060311 0.814802 -0.047017 11.00000 0.05176 0.09777 = 0.05408 0.00235 0.02286 -0.00229 O5 4 0.529339 0.315557 0.771055 11.00000 0.10409 0.12120 = 0.06737 -0.04367 0.02524 -0.02431 O6 4 0.455088 0.148357 0.762151 11.00000 0.11965 0.16271 = 0.06020 -0.01069 0.04283 -0.06206 O7 4 0.445893 0.195507 0.432087 11.00000 0.07236 0.13926 = 0.06256 0.02710 -0.02441 -0.04094 O8 4 0.524170 0.358788 0.439792 11.00000 0.14007 0.07647 = 0.09109 0.04124 -0.03746 -0.02445 C1 1 0.907200 0.873890 0.184827 11.00000 0.04115 0.03354 = 0.03512 -0.00329 0.00927 -0.00741 C2 1 0.978587 0.806278 0.181524 11.00000 0.03813 0.03809 = 0.03670 0.00610 -0.00147 -0.00095 C3 1 1.010574 0.773805 0.112785 11.00000 0.02563 0.04187 = 0.03989 0.00608 0.00413 0.00612 C4 1 0.967932 0.809453 0.047213 11.00000 0.03107 0.03517 = 0.03008 0.00292 0.00918 -0.00022 C5 1 0.895406 0.877633 0.048033 11.00000 0.02840 0.02682 = 0.03923 0.00725 -0.00058 -0.00626 C6 1 0.865079 0.912284 0.118455 11.00000 0.03282 0.02200 = 0.04762 0.00108 0.01093 -0.00263 C7 1 0.774026 1.104878 0.117853 11.00000 0.04759 0.03249 = 0.10588 0.01131 0.02908 0.00350 AFIX 43 H7 2 0.812653 1.170081 0.112687 11.00000 -1.20000 AFIX 0 C8 1 0.665823 1.003399 0.130370 11.00000 0.03835 0.04882 = 0.11595 0.01674 0.03001 0.00948 AFIX 43 H8 2 0.610622 0.986707 0.134893 11.00000 -1.20000 AFIX 0 C9 1 0.773895 0.888028 -0.041200 11.00000 0.04128 0.14205 = 0.06224 0.04149 -0.01168 -0.02097 AFIX 43 H9 2 0.735583 0.852927 -0.009795 11.00000 -1.20000 AFIX 0 C10 1 0.832199 0.965256 -0.133269 11.00000 0.05628 0.10901 = 0.04903 0.03199 -0.00766 -0.01386 AFIX 43 H10 2 0.840575 0.995841 -0.182109 11.00000 -1.20000 AFIX 0 C11 1 0.609845 0.110194 0.666109 11.00000 0.03748 0.03717 = 0.03625 0.00718 -0.00380 -0.00616 C12 1 0.540988 0.185400 0.667473 11.00000 0.03470 0.04367 = 0.03510 -0.00209 0.00751 -0.00949 C13 1 0.503890 0.234798 0.601580 11.00000 0.03353 0.03305 = 0.04590 -0.00321 0.00307 -0.00191 C14 1 0.537496 0.205593 0.533346 11.00000 0.03378 0.03554 = 0.03941 0.00254 -0.00190 -0.00191 C15 1 0.607330 0.132335 0.530395 11.00000 0.02984 0.03066 = 0.04084 -0.00520 0.00602 -0.00311 C16 1 0.644757 0.084952 0.597128 11.00000 0.03256 0.02389 = 0.04927 -0.00004 -0.00119 -0.00026 C17 1 0.741522 -0.101276 0.612769 11.00000 0.05052 0.03033 = 0.11687 0.01051 0.00174 0.00483 AFIX 43 H17 2 0.706293 -0.164513 0.629929 11.00000 -1.20000 AFIX 0 C18 1 0.842170 -0.001020 0.577521 11.00000 0.04491 0.04171 = 0.15705 0.00353 0.01681 0.00601 AFIX 43 H18 2 0.895640 0.016478 0.565706 11.00000 -1.20000 AFIX 0 C19 1 0.687679 0.182455 0.417000 11.00000 0.07782 0.07780 = 0.07217 -0.00751 0.02500 -0.02595 AFIX 43 H19 2 0.698218 0.270140 0.426332 11.00000 -1.20000 AFIX 0 C20 1 0.680752 0.001503 0.368779 11.00000 0.08386 0.10090 = 0.06534 -0.03312 0.03375 -0.02361 AFIX 43 H20 2 0.687856 -0.066266 0.334615 11.00000 -1.20000 AFIX 0 HKLF 4 REM cd16192 in P2(1)/c REM R1 = 0.0788 for 3958 Fo > 4sig(Fo) and 0.0965 for all 5161 data REM 433 parameters refined using 13 restraints END WGHT 0.0736 9.5534 REM Highest difference peak 0.544, deepest hole -0.331, 1-sigma level 0.098 Q1 1 1.0006 0.6863 0.1139 11.00000 0.05 0.54 Q2 1 0.7838 0.1966 0.3902 11.00000 0.05 0.48 Q3 1 0.9752 0.9211 0.2658 11.00000 0.05 0.47 Q4 1 1.0572 0.6355 0.1034 11.00000 0.05 0.46 Q5 1 0.5415 0.0550 0.7503 11.00000 0.05 0.45 Q6 1 0.5247 0.3453 0.6058 11.00000 0.05 0.43 Q7 1 0.8273 0.9627 0.2493 11.00000 0.05 0.41 Q8 1 0.5185 -0.0069 0.4156 11.00000 0.05 0.41 Q9 1 0.6874 0.1369 0.7359 11.00000 0.05 0.41 Q10 1 0.7677 1.0586 -0.2529 11.00000 0.05 0.40 Q11 1 0.4453 0.3372 0.4504 11.00000 0.05 0.37 Q12 1 0.6394 1.1468 0.1089 11.00000 0.05 0.37 Q13 1 0.3244 0.3232 0.6061 11.00000 0.05 0.37 Q14 1 0.6971 0.8380 -0.1117 11.00000 0.05 0.36 Q15 1 0.5999 0.0930 0.7657 11.00000 0.05 0.35 Q16 1 0.4538 0.4176 0.5951 11.00000 0.05 0.35 Q17 1 0.8043 0.8236 -0.0845 11.00000 0.05 0.35 Q18 1 0.4352 0.0433 0.7453 11.00000 0.05 0.34 Q19 1 0.4792 0.3105 0.6024 11.00000 0.05 0.33 Q20 1 0.8560 0.9967 0.1250 11.00000 0.05 0.32 ; _shelx_res_checksum 18354 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 0.86881(10) 0.90944(17) 0.27158(9) 0.0651(5) Uani 1 1 d . . Cl2 Cl 1.10009(9) 0.69006(17) 0.11153(9) 0.0616(5) Uani 1 1 d . . Cl3 Cl 0.65542(10) 0.05472(18) 0.75012(9) 0.0672(5) Uani 1 1 d . . Cl4 Cl 0.41889(8) 0.33082(15) 0.60539(9) 0.0582(4) Uani 1 1 d . . N1 N 1.0231(3) 0.7638(6) 0.2532(3) 0.0542(13) Uani 1 1 d . . N2 N 0.9990(3) 0.7643(5) -0.0258(2) 0.0446(11) Uani 1 1 d . . N3 N 0.8521(2) 0.9081(4) -0.0211(2) 0.0416(10) Uani 1 1 d . . N4 N 0.8913(3) 0.9584(5) -0.0807(3) 0.0541(13) Uani 1 1 d . . N5 N 0.7589(3) 0.9256(9) -0.1126(4) 0.101(3) Uani 1 1 d . . N6 N 0.7897(2) 0.9796(4) 0.1214(3) 0.0405(10) Uani 1 1 d . . N7 N 0.7201(3) 0.9116(5) 0.1310(4) 0.0629(15) Uani 1 1 d . . N8 N 0.6953(3) 1.1239(5) 0.1227(4) 0.0778(19) Uani 1 1 d . . N9 N 0.5050(3) 0.2180(6) 0.7417(3) 0.0540(12) Uani 1 1 d . . N10 N 0.4981(3) 0.2572(5) 0.4623(3) 0.0496(11) Uani 1 1 d . . N11 N 0.6412(3) 0.1060(4) 0.4594(3) 0.0445(11) Uani 1 1 d . . N12 N 0.6356(4) -0.0109(6) 0.4272(4) 0.082(2) Uani 1 1 d . . N13 N 0.7157(4) 0.1156(8) 0.3609(3) 0.085(2) Uani 1 1 d . . N14 N 0.7201(2) 0.0201(4) 0.5944(3) 0.0426(10) Uani 1 1 d . . N15 N 0.7858(3) 0.0854(5) 0.5703(4) 0.0637(15) Uani 1 1 d . . N16 N 0.8194(3) -0.1189(5) 0.6032(5) 0.089(2) Uani 1 1 d . . O1 O 1.0768(3) 0.8341(7) 0.2775(3) 0.101(2) Uani 1 1 d . . O2 O 1.0038(4) 0.6608(5) 0.2786(3) 0.0863(16) Uani 1 1 d . . O3 O 0.9619(3) 0.6760(5) -0.0568(3) 0.0720(13) Uani 1 1 d . . O4 O 1.0603(3) 0.8148(5) -0.0470(2) 0.0672(12) Uani 1 1 d . . O5 O 0.5293(4) 0.3156(6) 0.7711(3) 0.0968(19) Uani 1 1 d . . O6 O 0.4551(4) 0.1484(7) 0.7622(3) 0.113(2) Uani 1 1 d . . O7 O 0.4459(3) 0.1955(6) 0.4321(3) 0.0923(18) Uani 1 1 d . . O8 O 0.5242(4) 0.3588(5) 0.4398(3) 0.104(2) Uani 1 1 d . . C1 C 0.9072(3) 0.8739(5) 0.1848(3) 0.0364(11) Uani 1 1 d . . C2 C 0.9786(3) 0.8063(5) 0.1815(3) 0.0378(11) Uani 1 1 d . . C3 C 1.0106(3) 0.7738(5) 0.1128(3) 0.0357(11) Uani 1 1 d . . C4 C 0.9679(3) 0.8095(5) 0.0472(3) 0.0318(10) Uani 1 1 d . . C5 C 0.8954(3) 0.8776(4) 0.0480(3) 0.0316(10) Uani 1 1 d . . C6 C 0.8651(3) 0.9123(4) 0.1185(3) 0.0338(11) Uani 1 1 d . . C7 C 0.7740(4) 1.1049(5) 0.1179(4) 0.0611(18) Uani 1 1 d . . H7 H 0.8127 1.1701 0.1127 0.073 Uiso 1 1 calc R U C8 C 0.6658(4) 1.0034(6) 0.1304(4) 0.067(2) Uani 1 1 d . . H8 H 0.6106 0.9867 0.1349 0.080 Uiso 1 1 calc R U C9 C 0.7739(4) 0.8880(9) -0.0412(4) 0.082(3) Uani 1 1 d . . H9 H 0.7356 0.8529 -0.0098 0.099 Uiso 1 1 calc R U C10 C 0.8322(4) 0.9653(8) -0.1333(4) 0.072(2) Uani 1 1 d . . H10 H 0.8406 0.9958 -0.1821 0.086 Uiso 1 1 calc R U C11 C 0.6098(3) 0.1102(5) 0.6661(3) 0.0372(11) Uani 1 1 d . . C12 C 0.5410(3) 0.1854(5) 0.6675(3) 0.0376(11) Uani 1 1 d . . C13 C 0.5039(3) 0.2348(5) 0.6016(3) 0.0375(11) Uani 1 1 d . . C14 C 0.5375(3) 0.2056(5) 0.5333(3) 0.0364(11) Uani 1 1 d . . C15 C 0.6073(3) 0.1323(4) 0.5304(3) 0.0336(11) Uani 1 1 d . . C16 C 0.6448(3) 0.0850(4) 0.5971(3) 0.0353(11) Uani 1 1 d . . C17 C 0.7415(4) -0.1013(6) 0.6128(4) 0.0660(19) Uani 1 1 d . . H17 H 0.7063 -0.1645 0.6299 0.079 Uiso 1 1 calc R U C18 C 0.8422(4) -0.0010(6) 0.5775(5) 0.081(2) Uani 1 1 d . . H18 H 0.8956 0.0165 0.5657 0.097 Uiso 1 1 calc R U C19 C 0.6877(4) 0.1825(7) 0.4170(4) 0.075(2) Uani 1 1 d D U H19 H 0.6982 0.2701 0.4263 0.090 Uiso 1 1 calc R U C20 C 0.6808(5) 0.0015(8) 0.3688(4) 0.082(2) Uani 1 1 d D U H20 H 0.6879 -0.0663 0.3346 0.099 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 0.0734(10) 0.0775(11) 0.0464(9) -0.0148(8) 0.0227(7) 0.0049(9) Cl2 0.0463(8) 0.0785(11) 0.0608(9) 0.0208(8) 0.0121(7) 0.0323(7) Cl3 0.0654(10) 0.0849(12) 0.0501(9) 0.0227(8) -0.0115(7) 0.0021(9) Cl4 0.0429(8) 0.0622(9) 0.0696(10) -0.0105(7) 0.0029(7) 0.0172(7) N1 0.053(3) 0.071(4) 0.038(3) 0.009(3) -0.001(2) 0.006(3) N2 0.043(2) 0.052(3) 0.039(2) -0.003(2) 0.006(2) 0.006(2) N3 0.032(2) 0.048(3) 0.044(3) 0.017(2) -0.0006(18) -0.0053(19) N4 0.044(3) 0.072(3) 0.046(3) 0.022(2) 0.000(2) -0.010(2) N5 0.050(3) 0.179(8) 0.070(4) 0.058(5) -0.021(3) -0.029(4) N6 0.031(2) 0.029(2) 0.063(3) 0.0040(19) 0.012(2) -0.0010(17) N7 0.035(2) 0.039(3) 0.117(5) 0.011(3) 0.023(3) 0.000(2) N8 0.048(3) 0.044(3) 0.145(6) 0.023(3) 0.034(3) 0.017(2) N9 0.046(3) 0.076(4) 0.040(3) -0.008(3) 0.007(2) -0.012(3) N10 0.045(3) 0.061(3) 0.042(3) 0.008(2) 0.000(2) 0.001(2) N11 0.038(2) 0.050(3) 0.047(3) -0.008(2) 0.011(2) -0.004(2) N12 0.091(4) 0.080(4) 0.080(4) -0.038(3) 0.043(3) -0.039(3) N13 0.069(4) 0.128(6) 0.062(4) -0.025(4) 0.030(3) -0.025(4) N14 0.035(2) 0.027(2) 0.065(3) 0.001(2) 0.002(2) 0.0020(18) N15 0.037(3) 0.037(3) 0.118(5) 0.006(3) 0.008(3) 0.001(2) N16 0.054(3) 0.037(3) 0.175(7) 0.015(4) 0.013(4) 0.017(3) O1 0.084(4) 0.161(6) 0.055(3) 0.020(3) -0.028(3) -0.035(4) O2 0.119(4) 0.081(4) 0.058(3) 0.031(3) 0.001(3) 0.011(3) O3 0.089(3) 0.072(3) 0.056(3) -0.024(2) 0.015(2) -0.009(3) O4 0.052(2) 0.098(4) 0.054(3) 0.002(2) 0.023(2) -0.002(2) O5 0.104(4) 0.121(5) 0.067(3) -0.044(3) 0.025(3) -0.024(4) O6 0.120(5) 0.163(6) 0.060(3) -0.011(3) 0.043(3) -0.062(5) O7 0.072(3) 0.139(5) 0.063(3) 0.027(3) -0.024(3) -0.041(3) O8 0.140(5) 0.076(4) 0.091(4) 0.041(3) -0.037(4) -0.024(4) C1 0.041(3) 0.034(3) 0.035(3) -0.003(2) 0.009(2) -0.007(2) C2 0.038(3) 0.038(3) 0.037(3) 0.006(2) -0.001(2) -0.001(2) C3 0.026(2) 0.042(3) 0.040(3) 0.006(2) 0.004(2) 0.006(2) C4 0.031(2) 0.035(3) 0.030(2) 0.0029(19) 0.0092(19) 0.000(2) C5 0.028(2) 0.027(2) 0.039(3) 0.0073(19) -0.001(2) -0.0063(18) C6 0.033(2) 0.022(2) 0.048(3) 0.001(2) 0.011(2) -0.0026(19) C7 0.048(3) 0.032(3) 0.106(5) 0.011(3) 0.029(3) 0.004(2) C8 0.038(3) 0.049(4) 0.116(6) 0.017(4) 0.030(3) 0.009(3) C9 0.041(3) 0.142(7) 0.062(4) 0.041(5) -0.012(3) -0.021(4) C10 0.056(4) 0.109(6) 0.049(4) 0.032(4) -0.008(3) -0.014(4) C11 0.037(3) 0.037(3) 0.036(3) 0.007(2) -0.004(2) -0.006(2) C12 0.035(3) 0.044(3) 0.035(3) -0.002(2) 0.008(2) -0.009(2) C13 0.034(3) 0.033(3) 0.046(3) -0.003(2) 0.003(2) -0.002(2) C14 0.034(2) 0.036(3) 0.039(3) 0.003(2) -0.002(2) -0.002(2) C15 0.030(2) 0.031(2) 0.041(3) -0.005(2) 0.006(2) -0.0031(19) C16 0.033(2) 0.024(2) 0.049(3) 0.000(2) -0.001(2) -0.0003(19) C17 0.051(4) 0.030(3) 0.117(6) 0.011(3) 0.002(4) 0.005(3) C18 0.045(4) 0.042(4) 0.157(8) 0.004(4) 0.017(4) 0.006(3) C19 0.078(4) 0.078(4) 0.072(4) -0.008(4) 0.025(4) -0.026(4) C20 0.084(5) 0.101(5) 0.065(4) -0.033(4) 0.034(4) -0.024(4) 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 O2 N1 O1 127.1(6) O2 N1 C2 116.4(5) O1 N1 C2 116.4(5) O3 N2 O4 126.4(5) O3 N2 C4 116.0(4) O4 N2 C4 117.5(5) C9 N3 N4 110.0(5) C9 N3 C5 129.2(5) N4 N3 C5 120.7(4) C10 N4 N3 101.6(4) C9 N5 C10 102.6(5) C7 N6 N7 110.2(4) C7 N6 C6 130.0(4) N7 N6 C6 119.7(4) C8 N7 N6 102.0(5) C7 N8 C8 103.4(5) O6 N9 O5 127.9(6) O6 N9 C12 116.7(5) O5 N9 C12 115.4(5) O7 N10 O8 125.8(6) O7 N10 C14 118.0(5) O8 N10 C14 116.2(5) N12 N11 C19 108.7(5) N12 N11 C15 121.7(4) C19 N11 C15 129.4(5) C20 N12 N11 102.5(6) C19 N13 C20 102.6(6) C17 N14 N15 109.5(5) C17 N14 C16 131.0(5) N15 N14 C16 119.5(4) C18 N15 N14 102.0(5) C17 N16 C18 102.0(5) C2 C1 C6 120.2(4) C2 C1 Cl1 120.0(4) C6 C1 Cl1 119.8(4) C1 C2 C3 121.6(4) C1 C2 N1 119.9(4) C3 C2 N1 118.4(4) C4 C3 C2 118.0(4) C4 C3 Cl2 122.0(4) C2 C3 Cl2 120.0(4) C3 C4 C5 122.1(4) C3 C4 N2 117.5(4) C5 C4 N2 120.2(4) C4 C5 C6 118.8(4) C4 C5 N3 120.0(4) C6 C5 N3 121.1(4) C1 C6 C5 119.1(4) C1 C6 N6 120.5(4) C5 C6 N6 120.3(4) N6 C7 N8 109.5(5) N6 C7 H7 125.3 N8 C7 H7 125.3 N7 C8 N8 114.9(5) N7 C8 H8 122.6 N8 C8 H8 122.6 N5 C9 N3 109.7(6) N5 C9 H9 125.1 N3 C9 H9 125.1 N4 C10 N5 116.0(6) N4 C10 H10 122.0 N5 C10 H10 122.0 C12 C11 C16 119.8(4) C12 C11 Cl3 119.8(4) C16 C11 Cl3 120.4(4) C11 C12 C13 121.6(5) C11 C12 N9 120.3(5) C13 C12 N9 118.1(5) C12 C13 C14 118.1(4) C12 C13 Cl4 120.4(4) C14 C13 Cl4 121.5(4) C15 C14 C13 121.6(4) C15 C14 N10 119.8(4) C13 C14 N10 118.7(4) C14 C15 C16 119.8(4) C14 C15 N11 120.2(4) C16 C15 N11 120.0(4) C15 C16 C11 119.1(4) C15 C16 N14 119.4(4) C11 C16 N14 121.3(4) N16 C17 N14 110.2(6) N16 C17 H17 124.9 N14 C17 H17 124.9 N15 C18 N16 116.2(6) N15 C18 H18 121.9 N16 C18 H18 121.9 N13 C19 N11 110.0(6) N13 C19 C20 38.9(4) N11 C19 C20 71.2(4) N13 C19 H19 125.0 N11 C19 H19 125.0 C20 C19 H19 163.7 N12 C20 N13 116.0(6) N12 C20 C19 77.6(4) N13 C20 C19 38.5(4) N12 C20 H20 122.0 N13 C20 H20 122.0 C19 C20 H20 160.4 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C1 1.717(5) Cl2 C3 1.704(5) Cl3 C11 1.717(5) Cl4 C13 1.713(5) N1 O2 1.196(7) N1 O1 1.201(7) N1 C2 1.489(7) N2 O3 1.207(6) N2 O4 1.208(6) N2 C4 1.478(6) N3 C9 1.331(7) N3 N4 1.359(6) N3 C5 1.410(6) N4 C10 1.306(8) N5 C9 1.322(8) N5 C10 1.339(8) N6 C7 1.313(7) N6 N7 1.356(6) N6 C6 1.421(6) N7 C8 1.297(7) N8 C7 1.315(7) N8 C8 1.338(8) N9 O6 1.158(7) N9 O5 1.187(7) N9 C12 1.495(7) N10 O7 1.172(6) N10 O8 1.203(7) N10 C14 1.474(7) N11 N12 1.328(7) N11 C19 1.346(8) N11 C15 1.417(6) N12 C20 1.302(8) N13 C19 1.303(9) N13 C20 1.316(10) N14 C17 1.331(7) N14 N15 1.356(6) N14 C16 1.408(6) N15 C18 1.284(8) N16 C17 1.310(8) N16 C18 1.352(9) C1 C2 1.366(7) C1 C6 1.382(7) C2 C3 1.381(7) C3 C4 1.367(7) C4 C5 1.382(6) C5 C6 1.402(7) C7 H7 0.9300 C8 H8 0.9300 C9 H9 0.9300 C10 H10 0.9300 C11 C12 1.371(7) C11 C16 1.390(7) C12 C13 1.377(7) C13 C14 1.377(7) C14 C15 1.375(7) C15 C16 1.384(7) C17 H17 0.9300 C18 H18 0.9300 C19 C20 2.043(10) C19 H19 0.9300 C20 H20 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 C17 H17 N7 0.93 2.55 3.225(7) 129.9 4_566 C9 H9 N7 0.93 2.57 3.202(10) 125.6 . C8 H8 O6 0.93 2.56 3.211(8) 127.4 3_666 C7 H7 O4 0.93 2.44 3.158(7) 134.1 3_775 C7 H7 N15 0.93 2.65 3.296(7) 127.2 4_575 C17 H17 N7 0.93 2.55 3.225(7) 129.9 4_566 C9 H9 N7 0.93 2.57 3.202(10) 125.6 . C8 H8 O6 0.93 2.56 3.211(8) 127.4 3_666 C7 H7 O4 0.93 2.44 3.158(7) 134.1 3_775 C7 H7 N15 0.93 2.65 3.296(7) 127.2 4_575 C7 H7 N15 0.93 2.65 3.296(7) 127.2 4_575 C7 H7 O4 0.93 2.44 3.158(7) 134.1 3_775 C8 H8 O6 0.93 2.56 3.211(8) 127.4 3_666 C9 H9 N7 0.93 2.57 3.202(10) 125.6 . C17 H17 N7 0.93 2.55 3.225(7) 129.9 4_566 C7 H7 N15 0.93 2.65 3.296(7) 127.2 4_575 C7 H7 O4 0.93 2.44 3.158(7) 134.1 3_775 C8 H8 O6 0.93 2.56 3.211(8) 127.4 3_666 C9 H9 N7 0.93 2.57 3.202(10) 125.6 . C17 H17 N7 0.93 2.55 3.225(7) 129.9 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 C9 N3 N4 C10 0.1(8) C5 N3 N4 C10 176.6(6) C7 N6 N7 C8 1.7(7) C6 N6 N7 C8 -179.6(5) C19 N11 N12 C20 1.7(8) C15 N11 N12 C20 -173.5(6) C17 N14 N15 C18 -1.2(8) C16 N14 N15 C18 178.1(6) C6 C1 C2 C3 -0.3(7) Cl1 C1 C2 C3 178.8(4) C6 C1 C2 N1 -179.2(5) Cl1 C1 C2 N1 -0.1(7) O2 N1 C2 C1 87.6(7) O1 N1 C2 C1 -95.4(7) O2 N1 C2 C3 -91.4(6) O1 N1 C2 C3 85.6(7) C1 C2 C3 C4 -1.1(8) N1 C2 C3 C4 177.9(5) C1 C2 C3 Cl2 179.7(4) N1 C2 C3 Cl2 -1.4(7) C2 C3 C4 C5 0.9(7) Cl2 C3 C4 C5 -179.9(4) C2 C3 C4 N2 -174.8(4) Cl2 C3 C4 N2 4.4(7) O3 N2 C4 C3 104.7(6) O4 N2 C4 C3 -72.4(6) O3 N2 C4 C5 -71.1(6) O4 N2 C4 C5 111.8(5) C3 C4 C5 C6 0.6(7) N2 C4 C5 C6 176.2(4) C3 C4 C5 N3 -177.7(4) N2 C4 C5 N3 -2.1(7) C9 N3 C5 C4 129.1(7) N4 N3 C5 C4 -46.6(7) C9 N3 C5 C6 -49.1(9) N4 N3 C5 C6 135.2(5) C2 C1 C6 C5 1.8(7) Cl1 C1 C6 C5 -177.3(3) C2 C1 C6 N6 178.3(4) Cl1 C1 C6 N6 -0.8(6) C4 C5 C6 C1 -2.0(7) N3 C5 C6 C1 176.3(4) C4 C5 C6 N6 -178.4(4) N3 C5 C6 N6 -0.2(7) C7 N6 C6 C1 97.1(7) N7 N6 C6 C1 -81.3(6) C7 N6 C6 C5 -86.4(8) N7 N6 C6 C5 95.2(6) N7 N6 C7 N8 -1.7(8) C6 N6 C7 N8 179.8(6) C8 N8 C7 N6 0.8(9) N6 N7 C8 N8 -1.3(9) C7 N8 C8 N7 0.3(10) C10 N5 C9 N3 1.4(11) N4 N3 C9 N5 -1.0(10) C5 N3 C9 N5 -177.1(7) N3 N4 C10 N5 0.8(9) C9 N5 C10 N4 -1.4(11) C16 C11 C12 C13 1.5(7) Cl3 C11 C12 C13 178.2(4) C16 C11 C12 N9 -177.3(4) Cl3 C11 C12 N9 -0.7(7) O6 N9 C12 C11 -92.1(7) O5 N9 C12 C11 90.5(7) O6 N9 C12 C13 89.0(8) O5 N9 C12 C13 -88.4(7) C11 C12 C13 C14 0.6(7) N9 C12 C13 C14 179.5(4) C11 C12 C13 Cl4 -178.9(4) N9 C12 C13 Cl4 0.0(6) C12 C13 C14 C15 -1.8(7) Cl4 C13 C14 C15 177.7(4) C12 C13 C14 N10 179.6(4) Cl4 C13 C14 N10 -0.9(7) O7 N10 C14 C15 93.5(7) O8 N10 C14 C15 -85.0(7) O7 N10 C14 C13 -87.8(7) O8 N10 C14 C13 93.7(7) C13 C14 C15 C16 0.8(7) N10 C14 C15 C16 179.4(4) C13 C14 C15 N11 -178.8(4) N10 C14 C15 N11 -0.2(7) N12 N11 C15 C14 -106.3(7) C19 N11 C15 C14 79.6(8) N12 N11 C15 C16 74.1(7) C19 N11 C15 C16 -100.0(7) C14 C15 C16 C11 1.4(7) N11 C15 C16 C11 -179.0(4) C14 C15 C16 N14 -174.3(4) N11 C15 C16 N14 5.3(7) C12 C11 C16 C15 -2.5(7) Cl3 C11 C16 C15 -179.1(4) C12 C11 C16 N14 173.1(4) Cl3 C11 C16 N14 -3.6(6) C17 N14 C16 C15 -118.5(7) N15 N14 C16 C15 62.4(7) C17 N14 C16 C11 65.9(8) N15 N14 C16 C11 -113.2(6) C18 N16 C17 N14 -0.5(9) N15 N14 C17 N16 1.1(8) C16 N14 C17 N16 -178.1(6) N14 N15 C18 N16 0.9(10) C17 N16 C18 N15 -0.3(11) C20 N13 C19 N11 3.7(9) N12 N11 C19 N13 -3.6(9) C15 N11 C19 N13 171.1(6) N12 N11 C19 C20 -1.1(6) C15 N11 C19 C20 173.6(6) N11 N12 C20 N13 0.7(10) N11 N12 C20 C19 -1.1(5) C19 N13 C20 N12 -2.8(11)