#------------------------------------------------------------------------------ #$Date: 2024-11-05 03:32:29 +0200 (Tue, 05 Nov 2024) $ #$Revision: 295768 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160204.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_7160204 loop_ _publ_author_name 'Dong, Lin' 'Zhang, Chao' _publ_section_title ; Iridium-catalyzed tandem olefination/aza-Michael reaction: rapid access to N-N functionalized hydrazides ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB01631A _journal_year 2024 _chemical_formula_moiety 'C H Cl3, C33 H22 N2 O7' _chemical_formula_sum 'C34 H23 Cl3 N2 O7' _chemical_formula_weight 677.89 _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 _atom_sites_solution_primary dual _audit_creation_date 2024-07-20 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817) ; _audit_update_record ; 2024-08-28 deposited with the CCDC. 2024-11-04 downloaded from the CCDC. ; _cell_angle_alpha 81.5570(10) _cell_angle_beta 67.5690(10) _cell_angle_gamma 73.6290(10) _cell_formula_units_Z 2 _cell_length_a 11.40750(10) _cell_length_b 12.09380(10) _cell_length_c 13.11160(10) _cell_measurement_reflns_used 35884 _cell_measurement_temperature 300.57(10) _cell_measurement_theta_max 75.6720 _cell_measurement_theta_min 3.7940 _cell_volume 1602.65(3) _computing_cell_refinement 'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2014/7 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment air _diffrn_ambient_temperature 300.57(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.947 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 40.00 66.00 0.50 0.05 -- 66.00 76.00 1.65 52 2 \w 35.00 75.00 0.50 0.05 -- 62.00 77.00 114.11 80 3 \w 81.00 128.00 0.50 0.05 -- 62.00 77.00 114.11 94 4 \w 107.00 133.00 0.50 0.05 -- 66.00 76.00 1.65 52 5 \w 71.00 115.00 0.50 0.05 -- 44.45 37.00 60.00 88 6 \w 25.00 57.00 0.50 0.05 -- 44.45 37.00 60.00 64 7 \w 38.00 72.00 0.50 0.05 -- 66.00 80.00-122.40 68 8 \w 2.00 27.00 0.50 0.05 -- 38.00 97.00 -72.96 50 9 \w 8.00 33.00 0.50 0.05 -- 42.00 93.00 124.91 50 10 \w 18.00 43.00 0.50 0.05 -- 50.00 89.00 88.71 50 11 \w 18.00 43.00 0.50 0.05 -- 50.00 89.00 27.73 50 12 \w 18.00 43.00 0.50 0.05 -- 50.00 88.00 1.70 50 13 \w 3.00 28.00 0.50 0.05 -- 34.00 86.00 9.52 50 14 \w 18.00 43.00 0.50 0.05 -- 50.00 89.00-116.67 50 15 \w 15.00 40.00 0.50 0.05 -- 46.00 86.00-179.28 50 16 \w 20.00 45.00 0.50 0.05 -- 50.00 88.00-167.41 50 17 \w 100.00 126.00 0.50 0.11 -- 107.48 90.00-170.00 52 18 \w 29.00 55.00 0.50 0.05 -- 58.00 81.00 -62.92 52 19 \w 29.00 91.00 0.50 0.05 -- 58.00 81.00 172.23 124 20 \w 98.00 128.00 0.50 0.05 -- 58.00 81.00 172.23 60 21 \w -23.00 43.00 0.50 0.05 -- 44.45 -37.00 120.00 132 22 \w 51.00 117.00 0.50 0.11 -- 107.48-125.00 -90.00 132 23 \w 39.00 114.00 0.50 0.11 -- 107.48-125.00-120.00 150 24 \w 35.00 70.00 0.50 0.11 -- 107.48 -61.00-150.00 70 25 \w 35.00 60.00 0.50 0.11 -- 107.48 -61.00 -90.00 50 26 \w 34.00 87.00 0.50 0.11 -- 107.48 -90.00 74.00 106 27 \w 39.00 97.00 0.50 0.11 -- 107.48 -94.00 30.00 116 28 \w 45.00 107.00 0.50 0.11 -- 107.48 -94.00 -30.00 124 29 \w 36.00 100.00 0.50 0.11 -- 107.48 -94.00 -60.00 128 30 \w -22.00 75.00 0.50 0.05 -- 44.45 -90.00 74.00 194 31 \w -103.00 -77.00 0.50 0.05 -- -44.45 -57.00 0.00 52 32 \w -53.00 -27.00 0.50 0.05 -- -44.45 -57.00 0.00 52 33 \w -69.00 -25.00 0.50 0.05 -- -44.45 -57.00 -90.00 88 34 \w -48.00 -20.00 0.50 0.05 -- -44.45 -19.00-120.00 56 35 \w -51.00 -25.00 0.50 0.05 -- -44.45 -57.00-180.00 52 36 \w -117.00 -59.00 0.50 0.05 -- -44.45 -57.00-180.00 116 37 \w -121.00 -92.00 0.50 0.05 -- -44.45 -19.00-120.00 58 38 \w -154.00 -77.00 0.50 0.11 -- -102.00 -90.00 74.00 154 39 \w -70.00 -44.00 0.50 0.11 -- -74.00 -83.00 80.02 52 40 \w -58.00 -32.00 0.50 0.05 -- -62.00 -83.00 44.89 52 41 \w -70.00 -44.00 0.50 0.11 -- -74.00 -83.00 15.19 52 42 \w -54.00 -29.00 0.50 0.05 -- -58.00 -82.00 -36.94 50 43 \w -70.00 -33.00 0.50 0.05 -- -62.00 -82.00 -66.90 74 44 \w -119.00 -85.00 0.50 0.05 -- -58.00 -83.00-158.46 68 45 \w -83.00 -49.00 0.50 0.11 -- -78.00 -82.00-172.86 68 46 \w -53.00 -28.00 0.50 0.05 -- -58.00 -83.00-158.46 50 47 \w -76.00 -41.00 0.50 0.05 -- -70.00 -81.00 176.80 70 48 \w -135.00-109.00 0.50 0.05 -- -70.00 -81.00 176.80 52 49 \w -171.00-119.00 0.50 0.11 -- -98.00 -57.00 166.55 104 50 \w -79.00 -54.00 0.50 0.11 -- -82.00 -79.00 61.21 50 51 \w -105.00 -70.00 0.50 0.11 -- -98.00 -78.00 0.28 70 52 \w -112.00 -70.00 0.50 0.11 -- -98.00 -78.00 -38.19 84 53 \w -68.00 -42.00 0.50 0.05 -- -70.00 -80.00 -62.29 52 54 \w -169.00 -70.00 0.50 0.11 -- -98.00 -78.00 -70.94 198 55 \w -171.00-131.00 0.50 0.11 -- -98.00 -78.00 -38.19 80 56 \w -171.00-140.00 0.50 0.11 -- -98.00 -77.00-153.03 62 57 \w -134.00 -71.00 0.50 0.11 -- -98.00 -77.00-153.03 126 58 \w -103.00 -78.00 0.50 0.11 -- -102.00 -77.00-120.00 50 59 \w -175.00 -74.00 0.50 0.11 -- -102.00 -78.00 -23.93 202 60 \w -171.00-110.00 0.50 0.11 -- -98.00 -78.00 0.28 122 61 \w -89.00 -59.00 0.50 0.11 -- -86.00 -77.00 99.17 60 62 \w -155.00 -67.00 0.50 0.11 -- -94.00 -77.00 120.53 176 63 \w -100.00 -75.00 0.50 0.11 -- -102.00 -77.00 -16.38 50 64 \w -140.00-115.00 0.50 0.11 -- -102.00 -77.00 -16.38 50 65 \w -175.00-106.00 0.50 0.11 -- -102.00 -77.00-120.00 138 66 \w -171.00-114.00 0.50 0.11 -- -102.00 -77.00-138.05 114 67 \w -111.00 -77.00 0.50 0.11 -- -102.00 -77.00-138.05 68 68 \w -83.00 -57.00 0.50 0.11 -- -82.00 -76.00-138.78 52 69 \w -76.00 -51.00 0.50 0.11 -- -78.00 -76.00-116.90 50 70 \w -69.00 -44.00 0.50 0.05 -- -70.00 -75.00-103.21 50 71 \w -160.00 -77.00 0.50 0.11 -- -102.00 -76.00-173.13 166 72 \w -130.00-104.00 0.50 0.05 -- -70.00 -75.00-103.21 52 73 \w -167.00 -73.00 0.50 0.11 -- -98.00 -76.00 39.23 188 74 \w -77.00 -52.00 0.50 0.11 -- -78.00 -75.00 -37.43 50 75 \w -86.00 -60.00 0.50 0.11 -- -86.00 -75.00 -54.30 52 76 \w -163.00 -68.00 0.50 0.11 -- -94.00 -75.00 -95.67 190 77 \w -150.00 -68.00 0.50 0.11 -- -94.00 -75.00 -64.20 164 78 \w -85.00 -59.00 0.50 0.11 -- -86.00 -76.00 79.68 52 79 \w -82.00 -48.00 0.50 0.11 -- -74.00 -74.00 100.86 68 80 \w -137.00 -64.00 0.50 0.11 -- -90.00 -74.00 134.33 146 81 \w -144.00-118.00 0.50 0.11 -- -74.00 -75.00 138.90 52 82 \w -87.00 -61.00 0.50 0.11 -- -86.00 -74.00 177.64 52 83 \w -75.00 -49.00 0.50 0.11 -- -74.00 -75.00 138.90 52 84 \w -78.00 -46.00 0.50 0.05 -- -70.00 -70.00 70.54 64 85 \w -86.00 -60.00 0.50 0.11 -- -86.00 -74.00 33.60 52 86 \w -88.00 -61.00 0.50 0.11 -- -86.00 -73.00 -7.64 54 87 \w -155.00-119.00 0.50 0.11 -- -94.00 -69.00 55.30 72 88 \w -154.00-128.00 0.50 0.11 -- -86.00 -73.00 -7.64 52 89 \w -95.00 -70.00 0.50 0.11 -- -94.00 -69.00 55.30 50 90 \w -149.00-110.00 0.50 0.11 -- -90.00 -66.00 143.45 78 91 \w -124.00 -71.00 0.50 0.11 -- -94.00 -66.00 62.21 106 92 \w -102.00 -67.00 0.50 0.11 -- -90.00 -66.00 143.45 70 93 \w -175.00 -87.00 0.50 0.11 -- -102.00 -64.00 96.38 176 94 \w -137.00 -72.00 0.50 0.11 -- -94.00 -67.00 11.94 130 95 \w -91.00 -65.00 0.50 0.11 -- -90.00 -71.00-148.97 52 96 \w -109.00 -67.00 0.50 0.11 -- -90.00 -69.00-121.64 84 97 \w -69.00 -29.00 0.50 0.11 -- -102.00 61.00 -90.00 80 98 \w -91.00 -33.00 0.50 0.11 -- -102.00 125.00-120.00 116 99 \w -104.00 -56.00 0.50 0.11 -- -102.00 125.00 0.00 96 100 \w -117.00 -69.00 0.50 0.11 -- -102.00 125.00 90.00 96 101 \w -63.00 -37.00 0.50 0.11 -- -102.00 125.00 90.00 52 102 \w -116.00 -30.00 0.50 0.11 -- -102.00 125.00 120.00 172 103 \w -82.00 -51.00 0.50 0.11 -- -102.00 90.00-170.00 62 104 \w -66.00 29.00 0.50 0.05 -- -44.45 90.00-170.00 190 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, DW system, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0699030000 _diffrn_orient_matrix_UB_12 -0.1018921000 _diffrn_orient_matrix_UB_13 -0.0771150000 _diffrn_orient_matrix_UB_21 -0.0821552000 _diffrn_orient_matrix_UB_22 -0.0760505000 _diffrn_orient_matrix_UB_23 0.0861627000 _diffrn_orient_matrix_UB_31 -0.1053409000 _diffrn_orient_matrix_UB_32 0.0386798000 _diffrn_orient_matrix_UB_33 -0.0530932000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_unetI/netI 0.0130 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.947 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 46997 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.947 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.823 _diffrn_reflns_theta_min 3.813 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.028 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.58120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.405 _exptl_crystal_description block _exptl_crystal_F_000 696 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.549 _refine_diff_density_min -0.735 _refine_diff_density_rms 0.040 _refine_ls_extinction_coef 0.0045(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 416 _refine_ls_number_reflns 6332 _refine_ls_number_restraints 48 _refine_ls_restrained_S_all 1.106 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_gt 0.0515 _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^)+(0.0655P)^2^+0.6206P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1424 _refine_ls_wR_factor_ref 0.1450 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5762 _reflns_number_total 6332 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01631a2.cif _cod_data_source_block 3-co2ph_auto _cod_database_code 7160204 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula CHONCl _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_max 0.612 _shelx_estimated_absorpt_t_min 0.518 _reflns_odcompleteness_completeness 99.81 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Rigid bond restraints C13, C3, C19, C16, C14, C5 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 3. Uiso/Uaniso restraints and constraints Uanis(C13) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C5) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.2 4.a Ternary CH refined with riding coordinates: C4(H4), C33(H33) 4.b Secondary CH2 refined with riding coordinates: C18(H18A,H18B) 4.c Aromatic/amide H refined with riding coordinates: C22(H22), C28(H28), C30(H30), C32(H32), C9(H9), C19(H19), C5(H5), C21(H21), C11(H11), C23(H23), C3(H3), C25(H25), C13(H13), C27(H27), C7(H7), C29(H29), C15(H15), C31(H31), C2(H2) ; _shelx_res_file ; 3-co2ph_auto.res created by SHELXL-2014/7 TITL 3-co2ph_auto_a.res in P-1 REM Old TITL 3-CO2Ph_auto in P-1 REM SHELXT solution in P-1 REM R1 0.216, Rweak 0.018, Alpha 0.067, Orientation as input REM Formula found by SHELXT: C34 N2 O3 Cl2 CELL 1.54184 11.4075 12.0938 13.1116 81.557 67.569 73.629 ZERR 2 0.0001 0.0001 0.0001 0.001 0.001 0.001 LATT 1 SFAC C H Cl N O UNIT 68 46 6 4 14 ISOR 0.01 0.2 C13 C3 C19 C16 C14 C5 DELU C13 C3 C19 C16 C14 C5 L.S. 20 PLAN 1 SIZE 0.18 0.2 0.25 TEMP 27 CONF MORE -1 BOND $H fmap 2 acta OMIT 4 5 0 OMIT 5 -4 1 REM REM REM WGHT 0.065500 0.620600 EXTI 0.004522 FVAR 8.42415 CL1 3 -0.071411 0.216605 0.682758 11.00000 0.14582 0.11751 = 0.11685 0.01726 -0.06495 -0.05355 CL3 3 -0.133548 0.452690 0.609589 11.00000 0.06962 0.08578 = 0.28607 -0.00987 -0.02593 -0.01845 CL2 3 -0.007624 0.275003 0.454899 11.00000 0.17832 0.18815 = 0.11448 0.01039 -0.07606 -0.09784 O1 5 0.281515 0.285755 0.497184 11.00000 0.03921 0.07074 = 0.06155 -0.02004 -0.02110 -0.00373 O4 5 0.206169 0.214771 0.755092 11.00000 0.05671 0.04441 = 0.06384 -0.00993 -0.01454 -0.00299 O6 5 0.401545 0.434620 0.818779 11.00000 0.06692 0.06312 = 0.04813 -0.01331 -0.00650 -0.02474 O7 5 0.518124 0.561827 0.722530 11.00000 0.06600 0.06450 = 0.06003 -0.01869 -0.00474 -0.03018 O2 5 0.256929 0.580791 0.646448 11.00000 0.06178 0.05531 = 0.07034 -0.00178 -0.01741 -0.01852 O5 5 0.323810 0.080866 0.234751 11.00000 0.06875 0.06299 = 0.07162 -0.02497 -0.03595 -0.00248 O3 5 0.455003 -0.091453 0.173573 11.00000 0.08691 0.05943 = 0.07449 -0.02441 -0.04180 -0.00261 N1 4 0.256705 0.387538 0.679955 11.00000 0.03515 0.04736 = 0.04858 -0.01507 -0.00668 -0.00488 N2 4 0.376295 0.340950 0.601674 11.00000 0.03261 0.05642 = 0.04643 -0.01845 -0.00905 -0.00460 C1 1 0.375227 0.275811 0.522492 11.00000 0.03728 0.04910 = 0.04168 -0.00944 -0.01061 -0.00913 C4 1 0.492955 0.298214 0.633068 11.00000 0.03555 0.05224 = 0.04263 -0.01044 -0.01024 -0.00968 AFIX 13 H4 2 0.469040 0.258533 0.706063 11.00000 -1.20000 AFIX 0 C6 1 0.507617 0.196822 0.484111 11.00000 0.03386 0.04608 = 0.04060 -0.00668 -0.00821 -0.01028 C8 1 0.576526 0.210995 0.546452 11.00000 0.03612 0.04990 = 0.04365 -0.00926 -0.00889 -0.01188 C10 1 0.177355 0.318832 0.753092 11.00000 0.04059 0.04686 = 0.04369 -0.00994 -0.01406 -0.00445 C12 1 0.559081 0.112397 0.405158 11.00000 0.03919 0.04955 = 0.04147 -0.00883 -0.00731 -0.01179 C14 1 0.074951 0.512403 0.787419 11.00000 0.04433 0.04814 = 0.04755 -0.01116 -0.01536 -0.00229 C16 1 0.059567 0.401495 0.820292 11.00000 0.04150 0.04935 = 0.04252 -0.01012 -0.01160 -0.00261 C18 1 0.554791 0.393334 0.634602 11.00000 0.04233 0.06189 = 0.04954 -0.01457 -0.00883 -0.01768 AFIX 23 H18A 2 0.643982 0.359428 0.631203 11.00000 -1.20000 H18B 2 0.558093 0.444210 0.569603 11.00000 -1.20000 AFIX 0 C20 1 0.481041 0.462918 0.736031 11.00000 0.04370 0.05438 = 0.04831 -0.01012 -0.01504 -0.01362 C22 1 0.481352 0.096850 0.343818 11.00000 0.04628 0.05265 = 0.04519 -0.00930 -0.01178 -0.01253 AFIX 43 H22 2 0.404914 0.153304 0.348768 11.00000 -1.20000 AFIX 0 C24 1 0.203647 0.506321 0.696269 11.00000 0.04542 0.04634 = 0.04954 -0.00911 -0.01817 -0.00623 C26 1 0.431478 -0.008096 0.223660 11.00000 0.05696 0.05099 = 0.04660 -0.00977 -0.01710 -0.01032 C28 1 0.511865 0.008594 0.282052 11.00000 0.05139 0.05488 = 0.05049 -0.01199 -0.01666 -0.00850 AFIX 43 H28 2 0.589634 -0.046757 0.275104 11.00000 -1.20000 AFIX 0 C30 1 0.702279 0.144977 0.529645 11.00000 0.03671 0.06524 = 0.05872 -0.01558 -0.01566 -0.00951 AFIX 43 H30 2 0.750124 0.156424 0.569158 11.00000 -1.20000 AFIX 0 C32 1 0.685212 0.044453 0.391359 11.00000 0.04282 0.05889 = 0.05677 -0.02142 -0.00898 -0.00538 AFIX 43 H32 2 0.723156 -0.013143 0.340404 11.00000 -1.20000 AFIX 0 C34 1 0.461058 0.633031 0.814129 11.00000 0.06136 0.05265 = 0.05760 -0.01272 -0.01335 -0.02224 C17 1 0.246905 0.077676 0.174158 11.00000 0.06478 0.04747 = 0.05931 -0.01034 -0.02903 -0.00798 C9 1 0.754823 0.061003 0.451823 11.00000 0.03557 0.06698 = 0.06962 -0.02000 -0.01303 -0.00165 AFIX 43 H9 2 0.838808 0.014751 0.440021 11.00000 -1.20000 AFIX 0 C19 1 -0.051529 0.380710 0.903574 11.00000 0.05017 0.06262 = 0.05255 -0.00592 -0.00498 -0.00798 AFIX 43 H19 2 -0.061322 0.306044 0.924879 11.00000 -1.20000 AFIX 0 C5 1 -0.020813 0.606624 0.838048 11.00000 0.06029 0.04997 = 0.07126 -0.01769 -0.01764 0.00208 AFIX 43 H5 2 -0.011416 0.681397 0.816738 11.00000 -1.20000 AFIX 0 C21 1 0.292278 0.097947 0.061894 11.00000 0.07371 0.06044 = 0.06033 -0.00763 -0.02368 -0.01287 AFIX 43 H21 2 0.375872 0.109378 0.025076 11.00000 -1.20000 AFIX 0 C11 1 0.345778 0.713599 0.826161 11.00000 0.06554 0.05977 = 0.06657 -0.00389 -0.02279 -0.02141 AFIX 43 H11 2 0.301862 0.718267 0.778141 11.00000 -1.20000 AFIX 0 C23 1 0.296274 0.787924 0.911627 11.00000 0.07372 0.05570 = 0.08561 -0.01525 -0.01447 -0.01289 AFIX 43 H23 2 0.218595 0.844070 0.920581 11.00000 -1.20000 AFIX 0 C3 1 -0.147833 0.475464 0.954145 11.00000 0.04972 0.08096 = 0.05896 -0.01462 0.00108 -0.00371 AFIX 43 H3 2 -0.224122 0.464536 1.010368 11.00000 -1.20000 AFIX 0 C25 1 0.212617 0.101151 0.004495 11.00000 0.10678 0.07043 = 0.06497 -0.00688 -0.04370 -0.00744 AFIX 43 H25 2 0.242223 0.115427 -0.071619 11.00000 -1.20000 AFIX 0 C13 1 -0.132263 0.584971 0.922508 11.00000 0.05349 0.07148 = 0.07372 -0.02936 -0.00665 0.01036 AFIX 43 H13 2 -0.198191 0.646890 0.958549 11.00000 -1.20000 AFIX 0 C27 1 0.124339 0.060824 0.229671 11.00000 0.07199 0.08147 = 0.06871 0.00282 -0.02575 -0.02484 AFIX 43 H27 2 0.094211 0.047722 0.305930 11.00000 -1.20000 AFIX 0 C7 1 0.359718 0.780182 0.983191 11.00000 0.10606 0.06787 = 0.07141 -0.02155 -0.01992 -0.02886 AFIX 43 H7 2 0.325239 0.830567 1.040527 11.00000 -1.20000 AFIX 0 C29 1 0.090826 0.083595 0.058212 11.00000 0.10068 0.07535 = 0.11002 -0.01436 -0.07128 -0.00729 AFIX 43 H29 2 0.037757 0.085148 0.018721 11.00000 -1.20000 AFIX 0 C15 1 0.526305 0.623736 0.884316 11.00000 0.08012 0.07531 = 0.09591 -0.02344 -0.04538 -0.00648 AFIX 43 H15 2 0.604659 0.568336 0.874688 11.00000 -1.20000 AFIX 0 C31 1 0.473916 0.698146 0.970089 11.00000 0.12264 0.08857 = 0.08982 -0.02039 -0.05740 -0.02629 AFIX 43 H31 2 0.516797 0.692227 1.019142 11.00000 -1.20000 AFIX 0 C2 1 0.046109 0.063603 0.170519 11.00000 0.07440 0.09689 = 0.11370 0.00147 -0.04348 -0.03136 AFIX 43 H2 2 -0.037387 0.051854 0.207018 11.00000 -1.20000 AFIX 0 C33 1 -0.022765 0.319951 0.579389 11.00000 0.05784 0.09043 = 0.11498 -0.00534 -0.03805 -0.02694 AFIX 13 H33 2 0.062812 0.326966 0.574352 11.00000 -1.20000 AFIX 0 HKLF 4 REM 3-co2ph_auto_a.res in P-1 REM R1 = 0.0515 for 5762 Fo > 4sig(Fo) and 0.0544 for all 6332 data REM 416 parameters refined using 48 restraints END WGHT 0.0655 0.6207 REM Highest difference peak 0.549, deepest hole -0.735, 1-sigma level 0.040 Q1 1 -0.0864 0.4502 0.6253 11.00000 0.05 0.55 ; _shelx_res_checksum 444 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 2.065 _oxdiff_exptl_absorpt_empirical_full_min 0.739 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 Cl1 Cl -0.07141(12) 0.21660(9) 0.68276(9) 0.1191(3) Uani 1 1 d . . . . . Cl3 Cl -0.13355(9) 0.45269(8) 0.60959(14) 0.1588(6) Uani 1 1 d . . . . . Cl2 Cl -0.00762(14) 0.27500(12) 0.45490(9) 0.1434(5) Uani 1 1 d . . . . . O1 O 0.28152(12) 0.28575(13) 0.49718(12) 0.0565(3) Uani 1 1 d . . . . . O4 O 0.20617(14) 0.21477(11) 0.75509(12) 0.0584(4) Uani 1 1 d . . . . . O6 O 0.40155(15) 0.43462(13) 0.81878(11) 0.0606(4) Uani 1 1 d . . . . . O7 O 0.51812(15) 0.56183(13) 0.72253(12) 0.0642(4) Uani 1 1 d . . . . . O2 O 0.25693(15) 0.58079(13) 0.64645(13) 0.0636(4) Uani 1 1 d . . . . . O5 O 0.32381(15) 0.08087(13) 0.23475(13) 0.0651(4) Uani 1 1 d . . . . . O3 O 0.45500(17) -0.09145(13) 0.17357(14) 0.0707(4) Uani 1 1 d . . . . . N1 N 0.25670(14) 0.38754(13) 0.67995(12) 0.0460(3) Uani 1 1 d . . . . . N2 N 0.37629(13) 0.34095(13) 0.60167(12) 0.0463(3) Uani 1 1 d . . . . . C1 C 0.37523(16) 0.27581(15) 0.52249(14) 0.0433(4) Uani 1 1 d . . . . . C4 C 0.49296(16) 0.29821(16) 0.63307(14) 0.0440(4) Uani 1 1 d . . . . . H4 H 0.4690 0.2585 0.7061 0.053 Uiso 1 1 calc R U . . . C6 C 0.50762(15) 0.19682(15) 0.48411(14) 0.0411(4) Uani 1 1 d . . . . . C8 C 0.57653(16) 0.21099(15) 0.54645(14) 0.0438(4) Uani 1 1 d . . . . . C10 C 0.17736(17) 0.31883(15) 0.75309(14) 0.0445(4) Uani 1 1 d . . . . . C12 C 0.55908(17) 0.11240(15) 0.40516(14) 0.0447(4) Uani 1 1 d . . . . . C14 C 0.07495(18) 0.51240(16) 0.78742(15) 0.0480(4) Uani 1 1 d . U . . . C16 C 0.05957(17) 0.40150(16) 0.82029(14) 0.0465(4) Uani 1 1 d . U . . . C18 C 0.55479(18) 0.39333(18) 0.63460(16) 0.0512(4) Uani 1 1 d . . . . . H18A H 0.6440 0.3594 0.6312 0.061 Uiso 1 1 calc R U . . . H18B H 0.5581 0.4442 0.5696 0.061 Uiso 1 1 calc R U . . . C20 C 0.48104(18) 0.46292(16) 0.73603(15) 0.0480(4) Uani 1 1 d . . . . . C22 C 0.48135(18) 0.09685(16) 0.34382(15) 0.0486(4) Uani 1 1 d . . . . . H22 H 0.4049 0.1533 0.3488 0.058 Uiso 1 1 calc R U . . . C24 C 0.20365(18) 0.50632(15) 0.69627(15) 0.0471(4) Uani 1 1 d . . . . . C26 C 0.4315(2) -0.00810(17) 0.22366(15) 0.0518(4) Uani 1 1 d . . . . . C28 C 0.5119(2) 0.00859(17) 0.28205(16) 0.0527(4) Uani 1 1 d . . . . . H28 H 0.5896 -0.0468 0.2751 0.063 Uiso 1 1 calc R U . . . C30 C 0.70228(17) 0.14498(18) 0.52964(17) 0.0533(5) Uani 1 1 d . . . . . H30 H 0.7501 0.1564 0.5692 0.064 Uiso 1 1 calc R U . . . C32 C 0.68521(18) 0.04445(18) 0.39136(17) 0.0550(5) Uani 1 1 d . . . . . H32 H 0.7232 -0.0131 0.3404 0.066 Uiso 1 1 calc R U . . . C34 C 0.4611(2) 0.63303(18) 0.81413(17) 0.0567(5) Uani 1 1 d . . . . . C17 C 0.2469(2) 0.07768(17) 0.17416(17) 0.0555(5) Uani 1 1 d . . . . . C9 C 0.75482(19) 0.06100(19) 0.45182(19) 0.0597(5) Uani 1 1 d . . . . . H9 H 0.8388 0.0148 0.4400 0.072 Uiso 1 1 calc R U . . . C19 C -0.0515(2) 0.3807(2) 0.90357(17) 0.0602(5) Uani 1 1 d . U . . . H19 H -0.0613 0.3060 0.9249 0.072 Uiso 1 1 calc R U . . . C5 C -0.0208(2) 0.60662(19) 0.83805(19) 0.0641(5) Uani 1 1 d . U . . . H5 H -0.0114 0.6814 0.8167 0.077 Uiso 1 1 calc R U . . . C21 C 0.2923(2) 0.09795(19) 0.06189(19) 0.0652(5) Uani 1 1 d . . . . . H21 H 0.3759 0.1094 0.0251 0.078 Uiso 1 1 calc R U . . . C11 C 0.3458(2) 0.71360(19) 0.82616(19) 0.0628(5) Uani 1 1 d . . . . . H11 H 0.3019 0.7183 0.7781 0.075 Uiso 1 1 calc R U . . . C23 C 0.2963(3) 0.7879(2) 0.9116(2) 0.0753(7) Uani 1 1 d . . . . . H23 H 0.2186 0.8441 0.9206 0.090 Uiso 1 1 calc R U . . . C3 C -0.1478(2) 0.4755(2) 0.95415(19) 0.0710(6) Uani 1 1 d . U . . . H3 H -0.2241 0.4645 1.0104 0.085 Uiso 1 1 calc R U . . . C25 C 0.2126(3) 0.1012(2) 0.0045(2) 0.0795(7) Uani 1 1 d . . . . . H25 H 0.2422 0.1154 -0.0716 0.095 Uiso 1 1 calc R U . . . C13 C -0.1323(2) 0.5850(2) 0.9225(2) 0.0739(7) Uani 1 1 d . U . . . H13 H -0.1982 0.6469 0.9585 0.089 Uiso 1 1 calc R U . . . C27 C 0.1243(3) 0.0608(2) 0.2297(2) 0.0733(6) Uani 1 1 d . . . . . H27 H 0.0942 0.0477 0.3059 0.088 Uiso 1 1 calc R U . . . C7 C 0.3597(3) 0.7802(2) 0.9832(2) 0.0818(8) Uani 1 1 d . . . . . H7 H 0.3252 0.8306 1.0405 0.098 Uiso 1 1 calc R U . . . C29 C 0.0908(3) 0.0836(2) 0.0582(3) 0.0871(8) Uani 1 1 d . . . . . H29 H 0.0378 0.0851 0.0187 0.104 Uiso 1 1 calc R U . . . C15 C 0.5263(3) 0.6237(2) 0.8843(2) 0.0801(7) Uani 1 1 d . . . . . H15 H 0.6047 0.5683 0.8747 0.096 Uiso 1 1 calc R U . . . C31 C 0.4739(4) 0.6981(3) 0.9701(3) 0.0925(9) Uani 1 1 d . . . . . H31 H 0.5168 0.6922 1.0191 0.111 Uiso 1 1 calc R U . . . C2 C 0.0461(3) 0.0636(3) 0.1705(3) 0.0904(8) Uani 1 1 d . . . . . H2 H -0.0374 0.0519 0.2070 0.109 Uiso 1 1 calc R U . . . C33 C -0.0228(3) 0.3200(3) 0.5794(3) 0.0836(8) Uani 1 1 d . . . . . H33 H 0.0628 0.3270 0.5744 0.100 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 0.1458(8) 0.1175(7) 0.1168(7) 0.0173(5) -0.0650(6) -0.0536(6) Cl3 0.0696(5) 0.0858(6) 0.2861(17) -0.0099(7) -0.0259(7) -0.0184(4) Cl2 0.1783(11) 0.1881(11) 0.1145(7) 0.0104(7) -0.0761(7) -0.0978(9) O1 0.0392(7) 0.0707(9) 0.0616(8) -0.0200(7) -0.0211(6) -0.0037(6) O4 0.0567(8) 0.0444(7) 0.0638(8) -0.0099(6) -0.0145(7) -0.0030(6) O6 0.0669(9) 0.0631(8) 0.0481(7) -0.0133(6) -0.0065(7) -0.0247(7) O7 0.0660(9) 0.0645(9) 0.0600(8) -0.0187(7) -0.0047(7) -0.0302(7) O2 0.0618(9) 0.0553(8) 0.0703(9) -0.0018(7) -0.0174(7) -0.0185(7) O5 0.0687(9) 0.0630(9) 0.0716(9) -0.0250(7) -0.0359(8) -0.0025(7) O3 0.0869(11) 0.0594(9) 0.0745(10) -0.0244(7) -0.0418(9) -0.0026(8) N1 0.0351(7) 0.0474(8) 0.0486(8) -0.0151(6) -0.0067(6) -0.0049(6) N2 0.0326(7) 0.0564(9) 0.0464(8) -0.0184(6) -0.0091(6) -0.0046(6) C1 0.0373(8) 0.0491(9) 0.0417(8) -0.0094(7) -0.0106(7) -0.0091(7) C4 0.0355(8) 0.0522(9) 0.0426(8) -0.0104(7) -0.0102(7) -0.0097(7) C6 0.0339(8) 0.0461(9) 0.0406(8) -0.0067(7) -0.0082(6) -0.0103(7) C8 0.0361(8) 0.0499(9) 0.0436(9) -0.0093(7) -0.0089(7) -0.0119(7) C10 0.0406(9) 0.0469(9) 0.0437(9) -0.0099(7) -0.0141(7) -0.0045(7) C12 0.0392(8) 0.0496(9) 0.0415(8) -0.0088(7) -0.0073(7) -0.0118(7) C14 0.0443(9) 0.0481(9) 0.0476(9) -0.0112(7) -0.0154(8) -0.0023(7) C16 0.0415(9) 0.0493(9) 0.0425(9) -0.0101(7) -0.0116(7) -0.0026(7) C18 0.0423(9) 0.0619(11) 0.0495(10) -0.0146(8) -0.0088(8) -0.0177(8) C20 0.0437(9) 0.0544(10) 0.0483(10) -0.0101(8) -0.0150(8) -0.0136(8) C22 0.0463(9) 0.0527(10) 0.0452(9) -0.0093(7) -0.0118(7) -0.0125(8) C24 0.0454(9) 0.0463(9) 0.0495(9) -0.0091(8) -0.0182(8) -0.0062(7) C26 0.0570(11) 0.0510(10) 0.0466(9) -0.0098(8) -0.0171(8) -0.0103(8) C28 0.0514(10) 0.0549(10) 0.0505(10) -0.0120(8) -0.0167(8) -0.0085(8) C30 0.0367(9) 0.0652(12) 0.0587(11) -0.0156(9) -0.0157(8) -0.0095(8) C32 0.0428(10) 0.0589(11) 0.0568(11) -0.0214(9) -0.0090(8) -0.0054(8) C34 0.0614(12) 0.0526(10) 0.0576(11) -0.0127(9) -0.0134(9) -0.0222(9) C17 0.0648(12) 0.0475(10) 0.0593(11) -0.0103(8) -0.0290(10) -0.0080(9) C9 0.0356(9) 0.0670(12) 0.0696(13) -0.0200(10) -0.0130(9) -0.0016(8) C19 0.0502(11) 0.0626(12) 0.0525(11) -0.0059(9) -0.0050(9) -0.0080(9) C5 0.0603(12) 0.0500(11) 0.0713(13) -0.0177(9) -0.0176(10) 0.0021(9) C21 0.0737(14) 0.0604(12) 0.0603(12) -0.0076(10) -0.0237(11) -0.0129(10) C11 0.0655(13) 0.0598(12) 0.0666(13) -0.0039(10) -0.0228(10) -0.0214(10) C23 0.0737(15) 0.0557(12) 0.0856(17) -0.0153(11) -0.0145(13) -0.0129(11) C3 0.0497(11) 0.0810(15) 0.0590(12) -0.0146(11) 0.0011(9) -0.0037(10) C25 0.107(2) 0.0704(15) 0.0650(14) -0.0069(11) -0.0437(15) -0.0074(14) C13 0.0535(12) 0.0715(14) 0.0737(14) -0.0294(12) -0.0066(11) 0.0104(10) C27 0.0720(15) 0.0815(16) 0.0687(14) 0.0028(12) -0.0257(12) -0.0248(12) C7 0.106(2) 0.0679(15) 0.0714(15) -0.0215(12) -0.0199(14) -0.0289(15) C29 0.101(2) 0.0753(16) 0.110(2) -0.0144(15) -0.0713(19) -0.0073(15) C15 0.0801(16) 0.0753(15) 0.0959(19) -0.0234(14) -0.0454(15) -0.0065(13) C31 0.123(3) 0.0886(19) 0.0898(19) -0.0204(15) -0.0574(18) -0.0263(18) C2 0.0744(17) 0.097(2) 0.114(2) 0.0015(17) -0.0435(17) -0.0314(15) C33 0.0578(14) 0.0904(18) 0.115(2) -0.0053(16) -0.0380(14) -0.0269(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C20 O7 C34 116.62(15) . . ? C26 O5 C17 116.99(15) . . ? N2 N1 C10 122.19(14) . . ? N2 N1 C24 124.29(15) . . ? C10 N1 C24 113.51(14) . . ? N1 N2 C1 116.54(14) . . ? N1 N2 C4 119.82(14) . . ? C1 N2 C4 113.68(13) . . ? O1 C1 N2 124.10(16) . . ? O1 C1 C6 130.99(16) . . ? N2 C1 C6 104.90(14) . . ? N2 C4 H4 109.4 . . ? N2 C4 C8 100.56(13) . . ? N2 C4 C18 112.91(15) . . ? C8 C4 H4 109.4 . . ? C8 C4 C18 114.80(14) . . ? C18 C4 H4 109.4 . . ? C8 C6 C1 108.92(14) . . ? C8 C6 C12 122.10(16) . . ? C12 C6 C1 128.79(16) . . ? C6 C8 C4 110.92(15) . . ? C30 C8 C4 128.10(16) . . ? C30 C8 C6 120.87(16) . . ? O4 C10 N1 124.17(16) . . ? O4 C10 C16 131.03(18) . . ? N1 C10 C16 104.80(15) . . ? C6 C12 C22 120.60(16) . . ? C32 C12 C6 116.13(16) . . ? C32 C12 C22 123.26(16) . . ? C16 C14 C24 109.05(15) . . ? C5 C14 C16 120.75(18) . . ? C5 C14 C24 130.20(19) . . ? C14 C16 C10 108.73(16) . . ? C19 C16 C10 129.42(18) . . ? C19 C16 C14 121.85(17) . . ? C4 C18 H18A 109.1 . . ? C4 C18 H18B 109.1 . . ? H18A C18 H18B 107.8 . . ? C20 C18 C4 112.57(15) . . ? C20 C18 H18A 109.1 . . ? C20 C18 H18B 109.1 . . ? O6 C20 O7 123.84(17) . . ? O6 C20 C18 125.42(17) . . ? O7 C20 C18 110.72(16) . . ? C12 C22 H22 117.6 . . ? C28 C22 C12 124.85(18) . . ? C28 C22 H22 117.6 . . ? O2 C24 N1 125.07(17) . . ? O2 C24 C14 131.04(17) . . ? N1 C24 C14 103.86(15) . . ? O5 C26 C28 112.75(16) . . ? O3 C26 O5 122.86(19) . . ? O3 C26 C28 124.37(19) . . ? C22 C28 C26 124.50(19) . . ? C22 C28 H28 117.8 . . ? C26 C28 H28 117.8 . . ? C8 C30 H30 121.1 . . ? C8 C30 C9 117.78(18) . . ? C9 C30 H30 121.1 . . ? C12 C32 H32 119.3 . . ? C9 C32 C12 121.49(17) . . ? C9 C32 H32 119.3 . . ? C11 C34 O7 119.0(2) . . ? C15 C34 O7 119.0(2) . . ? C15 C34 C11 121.9(2) . . ? C21 C17 O5 119.8(2) . . ? C27 C17 O5 118.8(2) . . ? C27 C17 C21 121.3(2) . . ? C30 C9 H9 119.2 . . ? C32 C9 C30 121.57(18) . . ? C32 C9 H9 119.2 . . ? C16 C19 H19 121.3 . . ? C16 C19 C3 117.3(2) . . ? C3 C19 H19 121.3 . . ? C14 C5 H5 121.5 . . ? C14 C5 C13 117.1(2) . . ? C13 C5 H5 121.5 . . ? C17 C21 H21 120.4 . . ? C17 C21 C25 119.1(2) . . ? C25 C21 H21 120.4 . . ? C34 C11 H11 120.9 . . ? C34 C11 C23 118.2(2) . . ? C23 C11 H11 120.9 . . ? C11 C23 H23 119.5 . . ? C7 C23 C11 121.0(2) . . ? C7 C23 H23 119.5 . . ? C19 C3 H3 119.6 . . ? C13 C3 C19 120.9(2) . . ? C13 C3 H3 119.6 . . ? C21 C25 H25 119.8 . . ? C29 C25 C21 120.4(3) . . ? C29 C25 H25 119.8 . . ? C5 C13 H13 119.0 . . ? C3 C13 C5 122.08(19) . . ? C3 C13 H13 119.0 . . ? C17 C27 H27 120.6 . . ? C17 C27 C2 118.8(2) . . ? C2 C27 H27 120.6 . . ? C23 C7 H7 120.2 . . ? C31 C7 C23 119.7(2) . . ? C31 C7 H7 120.2 . . ? C25 C29 H29 120.0 . . ? C25 C29 C2 120.1(2) . . ? C2 C29 H29 120.0 . . ? C34 C15 H15 120.6 . . ? C34 C15 C31 118.8(3) . . ? C31 C15 H15 120.6 . . ? C7 C31 C15 120.4(3) . . ? C7 C31 H31 119.8 . . ? C15 C31 H31 119.8 . . ? C27 C2 H2 119.8 . . ? C29 C2 C27 120.3(3) . . ? C29 C2 H2 119.8 . . ? Cl1 C33 H33 108.7 . . ? Cl3 C33 Cl1 110.72(17) . . ? Cl3 C33 H33 108.7 . . ? Cl2 C33 Cl1 109.00(16) . . ? Cl2 C33 Cl3 110.96(18) . . ? Cl2 C33 H33 108.7 . . ? 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 Cl1 C33 1.740(3) . ? Cl3 C33 1.730(3) . ? Cl2 C33 1.727(3) . ? O1 C1 1.206(2) . ? O4 C10 1.207(2) . ? O6 C20 1.197(2) . ? O7 C20 1.344(2) . ? O7 C34 1.414(2) . ? O2 C24 1.200(2) . ? O5 C26 1.361(2) . ? O5 C17 1.401(2) . ? O3 C26 1.195(2) . ? N1 N2 1.3784(19) . ? N1 C10 1.399(2) . ? N1 C24 1.406(2) . ? N2 C1 1.398(2) . ? N2 C4 1.475(2) . ? C1 C6 1.481(2) . ? C4 H4 0.9800 . ? C4 C8 1.507(2) . ? C4 C18 1.515(2) . ? C6 C8 1.387(2) . ? C6 C12 1.403(2) . ? C8 C30 1.382(3) . ? C10 C16 1.476(2) . ? C12 C22 1.467(3) . ? C12 C32 1.399(3) . ? C14 C16 1.386(3) . ? C14 C24 1.488(3) . ? C14 C5 1.378(3) . ? C16 C19 1.380(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 C20 1.503(2) . ? C22 H22 0.9300 . ? C22 C28 1.321(3) . ? C26 C28 1.467(3) . ? C28 H28 0.9300 . ? C30 H30 0.9300 . ? C30 C9 1.388(3) . ? C32 H32 0.9300 . ? C32 C9 1.384(3) . ? C34 C11 1.367(3) . ? C34 C15 1.363(3) . ? C17 C21 1.371(3) . ? C17 C27 1.366(3) . ? C9 H9 0.9300 . ? C19 H19 0.9300 . ? C19 C3 1.385(3) . ? C5 H5 0.9300 . ? C5 C13 1.393(3) . ? C21 H21 0.9300 . ? C21 C25 1.374(4) . ? C11 H11 0.9300 . ? C11 C23 1.382(3) . ? C23 H23 0.9300 . ? C23 C7 1.366(4) . ? C3 H3 0.9300 . ? C3 C13 1.368(4) . ? C25 H25 0.9300 . ? C25 C29 1.359(4) . ? C13 H13 0.9300 . ? C27 H27 0.9300 . ? C27 C2 1.379(4) . ? C7 H7 0.9300 . ? C7 C31 1.364(4) . ? C29 H29 0.9300 . ? C29 C2 1.371(5) . ? C15 H15 0.9300 . ? C15 C31 1.383(4) . ? C31 H31 0.9300 . ? C2 H2 0.9300 . ? C33 H33 0.9800 . ? 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 O1 C1 C6 C8 -173.9(2) . . . . ? O1 C1 C6 C12 1.0(3) . . . . ? O4 C10 C16 C14 178.6(2) . . . . ? O4 C10 C16 C19 -1.2(4) . . . . ? O7 C34 C11 C23 -175.43(19) . . . . ? O7 C34 C15 C31 176.3(2) . . . . ? O5 C26 C28 C22 3.3(3) . . . . ? O5 C17 C21 C25 -176.2(2) . . . . ? O5 C17 C27 C2 176.7(2) . . . . ? O3 C26 C28 C22 -175.1(2) . . . . ? N1 N2 C1 O1 23.3(3) . . . . ? N1 N2 C1 C6 -155.42(15) . . . . ? N1 N2 C4 C8 154.80(15) . . . . ? N1 N2 C4 C18 -82.4(2) . . . . ? N1 C10 C16 C14 -1.6(2) . . . . ? N1 C10 C16 C19 178.6(2) . . . . ? N2 N1 C10 O4 0.7(3) . . . . ? N2 N1 C10 C16 -179.02(15) . . . . ? N2 N1 C24 O2 -2.0(3) . . . . ? N2 N1 C24 C14 179.37(15) . . . . ? N2 C1 C6 C8 4.73(19) . . . . ? N2 C1 C6 C12 179.68(17) . . . . ? N2 C4 C8 C6 -6.91(19) . . . . ? N2 C4 C8 C30 176.89(19) . . . . ? N2 C4 C18 C20 77.5(2) . . . . ? C1 N2 C4 C8 10.34(19) . . . . ? C1 N2 C4 C18 133.16(16) . . . . ? C1 C6 C8 C4 1.7(2) . . . . ? C1 C6 C8 C30 178.18(17) . . . . ? C1 C6 C12 C22 3.2(3) . . . . ? C1 C6 C12 C32 -175.48(18) . . . . ? C4 N2 C1 O1 169.03(18) . . . . ? C4 N2 C1 C6 -9.7(2) . . . . ? C4 C8 C30 C9 173.18(19) . . . . ? C4 C18 C20 O6 16.3(3) . . . . ? C4 C18 C20 O7 -164.88(16) . . . . ? C6 C8 C30 C9 -2.7(3) . . . . ? C6 C12 C22 C28 -168.20(19) . . . . ? C6 C12 C32 C9 -0.6(3) . . . . ? C8 C4 C18 C20 -167.98(16) . . . . ? C8 C6 C12 C22 177.57(17) . . . . ? C8 C6 C12 C32 -1.1(3) . . . . ? C8 C30 C9 C32 1.0(3) . . . . ? C10 N1 N2 C1 61.4(2) . . . . ? C10 N1 N2 C4 -82.1(2) . . . . ? C10 N1 C24 O2 176.68(18) . . . . ? C10 N1 C24 C14 -1.9(2) . . . . ? C10 C16 C19 C3 179.4(2) . . . . ? C12 C6 C8 C4 -173.69(16) . . . . ? C12 C6 C8 C30 2.8(3) . . . . ? C12 C22 C28 C26 178.04(18) . . . . ? C12 C32 C9 C30 0.6(3) . . . . ? C14 C16 C19 C3 -0.4(3) . . . . ? C14 C5 C13 C3 -0.5(4) . . . . ? C16 C14 C24 O2 -177.7(2) . . . . ? C16 C14 C24 N1 0.8(2) . . . . ? C16 C14 C5 C13 -0.1(3) . . . . ? C16 C19 C3 C13 -0.3(4) . . . . ? C18 C4 C8 C6 -128.41(17) . . . . ? C18 C4 C8 C30 55.4(3) . . . . ? C20 O7 C34 C11 -88.9(2) . . . . ? C20 O7 C34 C15 94.8(3) . . . . ? C22 C12 C32 C9 -179.2(2) . . . . ? C24 N1 N2 C1 -120.04(19) . . . . ? C24 N1 N2 C4 96.5(2) . . . . ? C24 N1 C10 O4 -177.98(18) . . . . ? C24 N1 C10 C16 2.3(2) . . . . ? C24 C14 C16 C10 0.5(2) . . . . ? C24 C14 C16 C19 -179.69(18) . . . . ? C24 C14 C5 C13 -179.8(2) . . . . ? C26 O5 C17 C21 -72.1(3) . . . . ? C26 O5 C17 C27 111.7(2) . . . . ? C32 C12 C22 C28 10.4(3) . . . . ? C34 O7 C20 O6 2.0(3) . . . . ? C34 O7 C20 C18 -176.87(18) . . . . ? C34 C11 C23 C7 -0.9(4) . . . . ? C34 C15 C31 C7 -0.8(5) . . . . ? C17 O5 C26 O3 -7.0(3) . . . . ? C17 O5 C26 C28 174.64(18) . . . . ? C17 C21 C25 C29 -0.5(4) . . . . ? C17 C27 C2 C29 -0.4(4) . . . . ? C19 C3 C13 C5 0.7(4) . . . . ? C5 C14 C16 C10 -179.23(18) . . . . ? C5 C14 C16 C19 0.6(3) . . . . ? C5 C14 C24 O2 2.0(4) . . . . ? C5 C14 C24 N1 -179.5(2) . . . . ? C21 C17 C27 C2 0.5(4) . . . . ? C21 C25 C29 C2 0.6(4) . . . . ? C11 C34 C15 C31 0.0(4) . . . . ? C11 C23 C7 C31 0.2(4) . . . . ? C23 C7 C31 C15 0.6(5) . . . . ? C25 C29 C2 C27 -0.2(5) . . . . ? C27 C17 C21 C25 -0.1(3) . . . . ? C15 C34 C11 C23 0.8(4) . . . . ?