#------------------------------------------------------------------------------ #$Date: 2024-10-30 20:34:16 +0200 (Wed, 30 Oct 2024) $ #$Revision: 295677 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126449.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_7126449 loop_ _publ_author_name 'Sch\"afer, Dominic' 'Fink, Fabian' 'Kleinschmidt, Denise' 'Keisers, Kristina' 'Thomas, Fabian' 'Hoffmann, Alexander' 'Pich, Andrij' 'Herres-Pawlis, Sonja' _publ_section_title ; Enhanced catalytic activity of copper complexes in microgels for aerobic oxidation of benzyl alcohols. ; _journal_issue 42 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 5601 _journal_page_last 5604 _journal_paper_doi 10.1039/d0cc02433c _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C8 H11 Cl2 Cu N5, 0.5(H2 O)' _chemical_formula_sum 'C8 H12 Cl2 Cu N5 O0.5' _chemical_formula_weight 320.66 _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 mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-03-06 deposited with the CCDC. 2020-04-23 downloaded from the CCDC. ; _cell_angle_alpha 110.78(3) _cell_angle_beta 103.66(3) _cell_angle_gamma 96.17(3) _cell_formula_units_Z 4 _cell_length_a 7.7357(15) _cell_length_b 12.816(3) _cell_length_c 13.522(3) _cell_measurement_reflns_used 13336 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 32.50 _cell_measurement_theta_min 2.78 _cell_volume 1190.6(6) _computing_cell_refinement ; X-Area Recipe 1.33.0.0 (STOE, 2015) ; _computing_data_collection ; X-Area Pilatus3_SV 1.31.131.0 (STOE, 2017) ; _computing_data_reduction ; X-Area Integrate 1.71.0.0 (STOE, 2016) X-Area LANA 1.71.4.0 (STOE, 2017) ; _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material ; STOE & Cie GmbH, X-Area, software package for collecting single-crystal or multi-domain crystal data on STOE area-detector diffractometers, for image processing, for the correction and scaling of reflection intensities and for outlier rejection, version 1.77, Darmstadt 2016 ; _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100 _diffrn_detector 'Hybrid Pixel Counting Detector' _diffrn_detector_area_resol_mean 5.81 _diffrn_detector_type 'Dectris Pilatus 200K' _diffrn_measured_fraction_theta_full 0.959 _diffrn_measured_fraction_theta_max 0.960 _diffrn_measurement_details ' 1227 frames, detector distance = 60 mm' _diffrn_measurement_device '4-circle diffractometer' _diffrn_measurement_device_type 'STOE STADIVARI' _diffrn_measurement_method 'rotation method, \w scans' _diffrn_radiation_collimation '0.6 mm diameter' _diffrn_radiation_monochromator 'Graded multilayer mirror' _diffrn_radiation_polarisn_norm 270 _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_unetI/netI 0.0453 _diffrn_reflns_Laue_measured_fraction_full 0.959 _diffrn_reflns_Laue_measured_fraction_max 0.960 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 8358 _diffrn_reflns_point_group_measured_fraction_full 0.959 _diffrn_reflns_point_group_measured_fraction_max 0.960 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.499 _diffrn_reflns_theta_min 2.772 _diffrn_source 'Genix Mo' _diffrn_source_current 1.000 _diffrn_source_power 0.050 _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 2.268 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_correction_T_min 0.1365 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; STOE X-Red32, absorption correction by Gaussian integration, analogous to P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic Computing", Munksgaard, Copenhagen (1970), 255 - 270. ; _exptl_crystal_colour blue-green _exptl_crystal_density_diffrn 1.789 _exptl_crystal_description rod _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.090 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.706 _refine_diff_density_min -0.764 _refine_diff_density_rms 0.156 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 322 _refine_ls_number_reflns 4269 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.097 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0659 _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^)+(0.0742P)^2^+9.8173P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1694 _refine_ls_wR_factor_ref 0.1753 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3873 _reflns_number_total 4269 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc02433c2.cif _cod_data_source_block C1 _cod_depositor_comments ; Adding full bibliography for 7126449.cif. 2024-10-30 Z value and formula fixed to values more according to usual chemical conventions. miguel ; _cod_original_formula_sum 'C16 H24 Cl4 Cu2 N10 O' _cod_original_formula_weight 641.33 _cod_original_formula_moiety '2(C8 H11 Cl2 Cu N5), H2 O' _cod_original_formula_units_Z 2 _cod_original_cell_volume 1190.6(5) _cod_database_code 7126449 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.773 _shelx_estimated_absorpt_t_max 0.839 _exptl_absorpt_special_details ; Afterwards scaling of reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different absorption corrections on the model structure of tetrakis(\m~2~-acetato)- diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140. Finally a spherical absorption correction was done within STOE LANA. ; _shelx_res_file ; TITL sh1115_a.res in P-1 sh1115_a.res created by SHELXL-2018/3 at 19:10:04 on 16-Oct-2019 REM Old TITL sh1115 in P-1 REM SHELXT solution in P-1: R1 0.134, Rweak 0.008, Alpha 0.053 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C21 N6 Cl4 Cu2 CELL 0.71073 7.7357 12.8159 13.5216 110.784 103.658 96.167 ZERR 2.000 0.0015 0.0026 0.0027 0.030 0.030 0.030 LATT 1 SFAC C H N CL CU O UNIT 32 48 20 8 4 2 L.S. 10 BOND $H ACTA CONF EQIV $1 x+1, y+1, z HTAB O1 Cl4_$1 EQIV $2 x+1, y, z HTAB C1 Cl1_$2 HTAB C2 Cl2_$2 HTAB C21 Cl3_$2 HTAB C21 Cl4_$2 HTAB C22 Cl4_$2 EQIV $3 -x+1, -y+1, -z+2 EQIV $4 -x, -y+1, -z+1 HTAB N5 Cl3_$4 HTAB N5 O1 HTAB N25 Cl1_$4 HTAB N25 Cl1 EQIV $5 -x+1, -y+2, -z+2 HTAB O1 Cl2_$5 DFIX 0.87 0.02 N25 H102 DFIX 0.87 0.02 N25 H103 SIZE .08 .09 .12 TEMP -173 LIST 4 FMAP 2 OMIT 0 51 PLAN -20 WGHT 0.074200 9.817301 FVAR 0.54160 CL1 4 0.123365 0.685196 0.715370 11.00000 0.01341 0.03707 = 0.02333 0.00755 0.00405 0.00270 O1 6 0.622732 1.024197 0.779379 11.00000 0.04032 0.02737 = 0.03123 0.00999 0.01579 0.00457 H105 2 0.644760 1.055508 0.735327 11.00000 0.06169 N1 3 0.794998 0.841487 0.947022 11.00000 0.01329 0.03005 = 0.03360 0.01623 0.01109 0.00587 C1 1 0.798550 0.745677 0.849429 11.00000 0.01496 0.01948 = 0.02859 0.00451 0.00785 0.00237 AFIX 13 H1 2 0.928955 0.746817 0.851818 11.00000 -1.20000 AFIX 0 CU2 5 0.400122 0.752916 0.848129 11.00000 0.01105 0.03058 = 0.02235 0.00932 0.00579 0.00273 CL2 4 0.279387 0.752907 0.987502 11.00000 0.01490 0.03660 = 0.02660 0.01173 0.00799 0.00361 N2 3 0.631146 0.866150 0.961100 11.00000 0.01898 0.02723 = 0.02565 0.01082 0.01269 0.00147 C2 1 0.933175 0.909321 1.036739 11.00000 0.01365 0.03235 = 0.02605 0.01281 0.00431 -0.00029 AFIX 43 H2 2 1.058216 0.906439 1.047880 11.00000 -1.20000 AFIX 0 CU3 5 -0.169171 0.297056 0.598422 11.00000 0.01368 0.03193 = 0.02896 0.01360 0.00763 0.00424 CL3 4 -0.387201 0.383357 0.536444 11.00000 0.01719 0.04245 = 0.03581 0.01987 0.01019 0.00968 N3 3 0.726121 0.639499 0.854956 11.00000 0.01438 0.02887 = 0.02354 0.00895 0.00441 0.00333 C3 1 0.860881 0.983890 1.109760 11.00000 0.02514 0.02446 = 0.02564 0.00916 0.00601 0.00095 AFIX 43 H3 2 0.924785 1.043508 1.179348 11.00000 -1.20000 AFIX 0 CL4 4 -0.360866 0.172800 0.629370 11.00000 0.01784 0.03723 = 0.04551 0.02118 0.01282 0.00587 N4 3 0.548854 0.616283 0.852044 11.00000 0.00950 0.03008 = 0.02537 0.00649 0.00657 0.00024 C4 1 0.674141 0.952555 1.059079 11.00000 0.02491 0.02462 = 0.02164 0.00736 0.01202 0.00696 AFIX 43 H4 2 0.587770 0.988538 1.090652 11.00000 -1.20000 AFIX 0 N5 3 0.515153 0.776095 0.735347 11.00000 0.01208 0.03656 = 0.02119 0.01156 0.00308 0.00402 C5 1 0.815786 0.560230 0.875717 11.00000 0.01758 0.03123 = 0.02990 0.00645 0.00687 0.00432 AFIX 43 H5 2 0.940023 0.558023 0.881493 11.00000 -1.20000 AFIX 0 C6 1 0.691299 0.484924 0.886487 11.00000 0.02915 0.02808 = 0.03009 0.00714 0.00607 0.00328 AFIX 43 H6 2 0.711001 0.419349 0.901326 11.00000 -1.20000 AFIX 0 C7 1 0.531868 0.522491 0.871671 11.00000 0.02123 0.02963 = 0.02597 0.00570 0.00517 -0.00296 AFIX 43 H7 2 0.421690 0.485347 0.875116 11.00000 -1.20000 AFIX 0 C8 1 0.701651 0.756029 0.741926 11.00000 0.01795 0.03935 = 0.03064 0.02040 0.00530 0.00441 AFIX 23 H8A 2 0.774701 0.819763 0.734665 11.00000 -1.20000 H8AB 2 0.695546 0.685042 0.678729 11.00000 -1.20000 AFIX 0 N21 3 0.203963 0.280047 0.696392 11.00000 0.01030 0.03020 = 0.02134 0.00762 0.00431 0.00190 C21 1 0.226845 0.279889 0.592006 11.00000 0.01749 0.02739 = 0.02279 0.00530 0.00881 0.00020 AFIX 13 H21 2 0.356026 0.275977 0.594163 11.00000 -1.20000 AFIX 0 N22 3 0.047538 0.300160 0.721759 11.00000 0.01515 0.03478 = 0.02362 0.01167 0.00482 0.00773 C22 1 0.320417 0.262079 0.776720 11.00000 0.01537 0.02334 = 0.03093 0.01274 0.00254 0.00208 AFIX 43 H22 2 0.436630 0.244786 0.776078 11.00000 -1.20000 AFIX 0 N23 3 0.111320 0.177931 0.501176 11.00000 0.01216 0.03141 = 0.02631 0.00937 0.00482 0.00303 C23 1 0.241606 0.273152 0.860037 11.00000 0.02207 0.02770 = 0.02505 0.01266 -0.00037 -0.00093 AFIX 43 H23 2 0.290965 0.266307 0.928249 11.00000 -1.20000 AFIX 0 N24 3 -0.074090 0.161912 0.477842 11.00000 0.01356 0.03568 = 0.02965 0.01284 0.00380 0.00521 C24 1 0.073565 0.296598 0.821762 11.00000 0.02257 0.02876 = 0.02283 0.00751 0.01371 0.00499 AFIX 43 H24 2 -0.013023 0.308725 0.861954 11.00000 -1.20000 AFIX 0 N25 3 0.002600 0.402615 0.566242 11.00000 0.01694 0.02224 = 0.02005 0.00572 0.00703 0.00194 C25 1 0.160962 0.083900 0.439103 11.00000 0.02504 0.03453 = 0.02451 0.01120 0.01208 0.00983 AFIX 43 H25 2 0.281777 0.073756 0.442509 11.00000 -1.20000 AFIX 0 C26 1 0.004556 0.006502 0.370751 11.00000 0.03359 0.02996 = 0.02292 0.00609 0.01057 0.00565 AFIX 43 H26 2 -0.005612 -0.067037 0.316135 11.00000 -1.20000 AFIX 0 C27 1 -0.137775 0.058263 0.398041 11.00000 0.02262 0.03526 = 0.02840 0.01092 0.00714 -0.00158 AFIX 43 H27 2 -0.263284 0.023743 0.363940 11.00000 -1.20000 AFIX 0 C28 1 0.192650 0.389179 0.577539 11.00000 0.00946 0.02955 = 0.02626 0.00928 0.00685 -0.00224 AFIX 23 H28A 2 0.274128 0.455376 0.642219 11.00000 -1.20000 H28B 2 0.224276 0.389701 0.510891 11.00000 -1.20000 REM ##### REM ##### AFIX 0 H100 2 0.443311 0.741169 0.671209 11.00000 0.02145 H101 2 0.522534 0.856845 0.744316 11.00000 0.03903 H102 2 -0.049243 0.387998 0.496813 11.00000 0.02082 H103 2 0.005857 0.473341 0.608514 11.00000 0.02673 H104 2 0.630352 1.079319 0.829455 11.00000 0.01481 HKLF 4 REM sh1115_a.res in P-1 REM wR2 = 0.1753, GooF = S = 1.097, Restrained GooF = 1.097 for all data REM R1 = 0.0659 for 3873 Fo > 4sig(Fo) and 0.0736 for all 4269 data REM 322 parameters refined using 2 restraints END WGHT 0.0742 9.8172 REM Highest difference peak 0.706, deepest hole -0.764, 1-sigma level 0.156 Q1 1 0.3339 0.7357 0.9014 11.00000 0.05 0.71 Q2 1 0.4562 0.8130 0.9190 11.00000 0.05 0.70 Q3 1 0.0301 0.6601 0.6614 11.00000 0.05 0.69 Q4 1 0.3680 0.6931 0.7726 11.00000 0.05 0.69 Q5 1 -0.0323 0.3019 0.6536 11.00000 0.05 0.67 Q6 1 -0.1361 0.3665 0.5816 11.00000 0.05 0.65 Q7 1 -0.2198 0.2299 0.5327 11.00000 0.05 0.65 Q8 1 -0.4454 0.3123 0.4782 11.00000 0.05 0.63 Q9 1 0.4627 0.7782 0.8098 11.00000 0.05 0.62 Q10 1 0.3243 0.7922 0.9683 11.00000 0.05 0.60 Q11 1 -0.3610 0.2653 0.5819 11.00000 0.05 0.59 Q12 1 0.7261 0.8889 1.0968 11.00000 0.05 0.58 Q13 1 -0.4413 0.2942 0.5428 11.00000 0.05 0.56 Q14 1 -0.3019 0.2871 0.5343 11.00000 0.05 0.55 Q15 1 0.5075 0.7549 0.9029 11.00000 0.05 0.54 Q16 1 -0.1967 0.2115 0.6220 11.00000 0.05 0.54 Q17 1 0.1167 0.3673 0.5904 11.00000 0.05 0.53 Q18 1 0.0060 0.0583 0.4233 11.00000 0.05 0.52 Q19 1 0.1049 0.6324 0.7472 11.00000 0.05 0.51 Q20 1 0.2016 0.7500 0.7757 11.00000 0.05 0.51 ; _shelx_res_checksum 26027 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 0.12336(19) 0.68520(14) 0.71537(12) 0.0263(4) Uani 1 1 d . . . . . O1 O 0.6227(7) 1.0242(5) 0.7794(5) 0.0327(11) Uani 1 1 d . . . . . H105 H 0.645(14) 1.056(9) 0.735(9) 0.06(3) Uiso 1 1 d . . . . . N1 N 0.7950(7) 0.8415(5) 0.9470(5) 0.0237(11) Uani 1 1 d . . . . . C1 C 0.7985(8) 0.7457(5) 0.8494(5) 0.0223(13) Uani 1 1 d . . . . . H1 H 0.928955 0.746817 0.851818 0.027 Uiso 1 1 calc R U . . . Cu2 Cu 0.40012(9) 0.75292(7) 0.84813(6) 0.0216(2) Uani 1 1 d . . . . . Cl2 Cl 0.2794(2) 0.75291(14) 0.98750(13) 0.0260(4) Uani 1 1 d . . . . . N2 N 0.6311(7) 0.8662(5) 0.9611(4) 0.0230(11) Uani 1 1 d . . . . . C2 C 0.9332(8) 0.9093(6) 1.0367(5) 0.0243(13) Uani 1 1 d . . . . . H2 H 1.058216 0.906439 1.047880 0.029 Uiso 1 1 calc R U . . . Cu3 Cu -0.16917(10) 0.29706(7) 0.59842(6) 0.0242(2) Uani 1 1 d . . . . . Cl3 Cl -0.3872(2) 0.38336(15) 0.53644(14) 0.0298(4) Uani 1 1 d . . . . . N3 N 0.7261(7) 0.6395(5) 0.8550(4) 0.0230(11) Uani 1 1 d . . . . . C3 C 0.8609(9) 0.9839(6) 1.1098(5) 0.0259(14) Uani 1 1 d . . . . . H3 H 0.924785 1.043508 1.179348 0.031 Uiso 1 1 calc R U . . . Cl4 Cl -0.3609(2) 0.17280(15) 0.62937(15) 0.0315(4) Uani 1 1 d . . . . . N4 N 0.5489(7) 0.6163(5) 0.8520(4) 0.0230(11) Uani 1 1 d . . . . . C4 C 0.6741(9) 0.9526(5) 1.0591(5) 0.0231(13) Uani 1 1 d . . . . . H4 H 0.587770 0.988538 1.090652 0.028 Uiso 1 1 calc R U . . . N5 N 0.5152(7) 0.7761(5) 0.7353(5) 0.0237(11) Uani 1 1 d . . . . . C5 C 0.8158(9) 0.5602(6) 0.8757(6) 0.0279(14) Uani 1 1 d . . . . . H5 H 0.940023 0.558023 0.881493 0.034 Uiso 1 1 calc R U . . . C6 C 0.6913(10) 0.4849(6) 0.8865(6) 0.0311(15) Uani 1 1 d . . . . . H6 H 0.711001 0.419349 0.901326 0.037 Uiso 1 1 calc R U . . . C7 C 0.5319(9) 0.5225(6) 0.8717(5) 0.0281(14) Uani 1 1 d . . . . . H7 H 0.421690 0.485347 0.875116 0.034 Uiso 1 1 calc R U . . . C8 C 0.7017(9) 0.7560(6) 0.7419(6) 0.0279(14) Uani 1 1 d . . . . . H8A H 0.774701 0.819763 0.734665 0.033 Uiso 1 1 calc R U . . . H8AB H 0.695546 0.685042 0.678729 0.033 Uiso 1 1 calc R U . . . N21 N 0.2040(7) 0.2800(5) 0.6964(4) 0.0216(11) Uani 1 1 d . . . . . C21 C 0.2268(8) 0.2799(5) 0.5920(5) 0.0237(13) Uani 1 1 d . . . . . H21 H 0.356026 0.275977 0.594163 0.028 Uiso 1 1 calc R U . . . N22 N 0.0475(7) 0.3002(5) 0.7218(4) 0.0244(11) Uani 1 1 d . . . . . C22 C 0.3204(8) 0.2621(5) 0.7767(5) 0.0236(13) Uani 1 1 d . . . . . H22 H 0.436630 0.244786 0.776078 0.028 Uiso 1 1 calc R U . . . N23 N 0.1113(7) 0.1779(5) 0.5012(4) 0.0242(11) Uani 1 1 d . . . . . C23 C 0.2416(9) 0.2732(5) 0.8600(5) 0.0261(14) Uani 1 1 d . . . . . H23 H 0.290965 0.266307 0.928249 0.031 Uiso 1 1 calc R U . . . N24 N -0.0741(7) 0.1619(5) 0.4778(5) 0.0268(12) Uani 1 1 d . . . . . C24 C 0.0736(9) 0.2966(5) 0.8218(5) 0.0242(13) Uani 1 1 d . . . . . H24 H -0.013023 0.308725 0.861954 0.029 Uiso 1 1 calc R U . . . N25 N 0.0026(7) 0.4026(4) 0.5662(4) 0.0204(11) Uani 1 1 d D . . . . C25 C 0.1610(9) 0.0839(6) 0.4391(5) 0.0270(14) Uani 1 1 d . . . . . H25 H 0.281777 0.073756 0.442509 0.032 Uiso 1 1 calc R U . . . C26 C 0.0046(10) 0.0065(6) 0.3708(5) 0.0297(15) Uani 1 1 d . . . . . H26 H -0.005612 -0.067037 0.316135 0.036 Uiso 1 1 calc R U . . . C27 C -0.1378(9) 0.0583(6) 0.3980(6) 0.0299(15) Uani 1 1 d . . . . . H27 H -0.263284 0.023743 0.363940 0.036 Uiso 1 1 calc R U . . . C28 C 0.1926(8) 0.3892(5) 0.5775(5) 0.0225(13) Uani 1 1 d . . . . . H28A H 0.274128 0.455376 0.642219 0.027 Uiso 1 1 calc R U . . . H28B H 0.224276 0.389701 0.510891 0.027 Uiso 1 1 calc R U . . . H100 H 0.443(10) 0.741(6) 0.671(6) 0.021(18) Uiso 1 1 d . . . . . H101 H 0.523(11) 0.857(8) 0.744(7) 0.04(2) Uiso 1 1 d . . . . . H102 H -0.049(9) 0.388(6) 0.497(2) 0.021(18) Uiso 1 1 d D . . . . H103 H 0.006(10) 0.473(3) 0.609(5) 0.027(19) Uiso 1 1 d D . . . . H104 H 0.630(9) 1.079(6) 0.829(6) 0.015(18) Uiso 1 1 d . . . . . 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 0.0134(7) 0.0371(9) 0.0233(7) 0.0075(7) 0.0040(6) 0.0027(6) O1 0.040(3) 0.027(3) 0.031(3) 0.010(3) 0.016(2) 0.005(2) N1 0.013(2) 0.030(3) 0.034(3) 0.016(2) 0.011(2) 0.006(2) C1 0.015(3) 0.019(3) 0.029(3) 0.005(3) 0.008(2) 0.002(2) Cu2 0.0111(4) 0.0306(4) 0.0224(4) 0.0093(3) 0.0058(3) 0.0027(3) Cl2 0.0149(7) 0.0366(9) 0.0266(8) 0.0117(7) 0.0080(6) 0.0036(6) N2 0.019(3) 0.027(3) 0.026(3) 0.011(2) 0.013(2) 0.001(2) C2 0.014(3) 0.032(3) 0.026(3) 0.013(3) 0.004(2) 0.000(2) Cu3 0.0137(4) 0.0319(5) 0.0290(4) 0.0136(4) 0.0076(3) 0.0042(3) Cl3 0.0172(7) 0.0425(9) 0.0358(9) 0.0199(8) 0.0102(6) 0.0097(7) N3 0.014(2) 0.029(3) 0.024(3) 0.009(2) 0.004(2) 0.003(2) C3 0.025(3) 0.024(3) 0.026(3) 0.009(3) 0.006(3) 0.001(3) Cl4 0.0178(7) 0.0372(9) 0.0455(10) 0.0212(8) 0.0128(7) 0.0059(6) N4 0.010(2) 0.030(3) 0.025(3) 0.006(2) 0.007(2) 0.000(2) C4 0.025(3) 0.025(3) 0.022(3) 0.007(3) 0.012(3) 0.007(3) N5 0.012(2) 0.037(3) 0.021(3) 0.012(3) 0.003(2) 0.004(2) C5 0.018(3) 0.031(4) 0.030(3) 0.006(3) 0.007(3) 0.004(3) C6 0.029(4) 0.028(4) 0.030(4) 0.007(3) 0.006(3) 0.003(3) C7 0.021(3) 0.030(3) 0.026(3) 0.006(3) 0.005(3) -0.003(3) C8 0.018(3) 0.039(4) 0.031(3) 0.020(3) 0.005(3) 0.004(3) N21 0.010(2) 0.030(3) 0.021(3) 0.008(2) 0.004(2) 0.002(2) C21 0.017(3) 0.027(3) 0.023(3) 0.005(3) 0.009(2) 0.000(2) N22 0.015(3) 0.035(3) 0.024(3) 0.012(2) 0.005(2) 0.008(2) C22 0.015(3) 0.023(3) 0.031(3) 0.013(3) 0.003(3) 0.002(2) N23 0.012(2) 0.031(3) 0.026(3) 0.009(2) 0.005(2) 0.003(2) C23 0.022(3) 0.028(3) 0.025(3) 0.013(3) 0.000(3) -0.001(3) N24 0.014(3) 0.036(3) 0.030(3) 0.013(3) 0.004(2) 0.005(2) C24 0.023(3) 0.029(3) 0.023(3) 0.008(3) 0.014(3) 0.005(3) N25 0.017(3) 0.022(3) 0.020(3) 0.006(2) 0.007(2) 0.002(2) C25 0.025(3) 0.035(4) 0.025(3) 0.011(3) 0.012(3) 0.010(3) C26 0.034(4) 0.030(4) 0.023(3) 0.006(3) 0.011(3) 0.006(3) C27 0.023(3) 0.035(4) 0.028(3) 0.011(3) 0.007(3) -0.002(3) C28 0.009(3) 0.030(3) 0.026(3) 0.009(3) 0.007(2) -0.002(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' N N 0.0061 0.0033 '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' Cu Cu 0.3201 1.2651 '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 H105 O1 H104 98(8) . . ? C2 N1 N2 110.4(5) . . ? C2 N1 C1 129.2(5) . . ? N2 N1 C1 120.1(5) . . ? N3 C1 N1 109.6(5) . . ? N3 C1 C8 112.7(5) . . ? N1 C1 C8 112.2(5) . . ? N3 C1 H1 107.4 . . ? N1 C1 H1 107.4 . . ? C8 C1 H1 107.4 . . ? N5 Cu2 N2 83.9(2) . . ? N5 Cu2 N4 90.0(2) . . ? N2 Cu2 N4 87.0(2) . . ? N5 Cu2 Cl1 89.36(16) . . ? N2 Cu2 Cl1 159.56(16) . . ? N4 Cu2 Cl1 112.34(15) . . ? N5 Cu2 Cl2 172.30(19) . . ? N2 Cu2 Cl2 90.90(15) . . ? N4 Cu2 Cl2 95.44(15) . . ? Cl1 Cu2 Cl2 93.64(6) . . ? C4 N2 N1 105.1(5) . . ? C4 N2 Cu2 137.2(4) . . ? N1 N2 Cu2 116.7(4) . . ? N1 C2 C3 107.8(6) . . ? N1 C2 H2 126.1 . . ? C3 C2 H2 126.1 . . ? N25 Cu3 N22 87.8(2) . . ? N25 Cu3 N24 82.6(2) . . ? N22 Cu3 N24 88.0(2) . . ? N25 Cu3 Cl3 85.38(16) . . ? N22 Cu3 Cl3 149.56(17) . . ? N24 Cu3 Cl3 120.27(15) . . ? N25 Cu3 Cl4 177.86(16) . . ? N22 Cu3 Cl4 92.50(17) . . ? N24 Cu3 Cl4 95.32(16) . . ? Cl3 Cu3 Cl4 95.42(7) . . ? N4 N3 C5 111.4(5) . . ? N4 N3 C1 119.2(5) . . ? C5 N3 C1 129.0(5) . . ? C2 C3 C4 104.8(6) . . ? C2 C3 H3 127.6 . . ? C4 C3 H3 127.6 . . ? C7 N4 N3 104.3(5) . . ? C7 N4 Cu2 139.4(4) . . ? N3 N4 Cu2 115.1(4) . . ? N2 C4 C3 111.7(6) . . ? N2 C4 H4 124.1 . . ? C3 C4 H4 124.1 . . ? C8 N5 Cu2 117.9(4) . . ? C8 N5 H100 112(5) . . ? Cu2 N5 H100 110(5) . . ? C8 N5 H101 106(5) . . ? Cu2 N5 H101 108(5) . . ? H100 N5 H101 102(7) . . ? C6 C5 N3 106.0(6) . . ? C6 C5 H5 127.0 . . ? N3 C5 H5 127.0 . . ? C5 C6 C7 106.2(6) . . ? C5 C6 H6 126.9 . . ? C7 C6 H6 126.9 . . ? N4 C7 C6 112.2(6) . . ? N4 C7 H7 123.9 . . ? C6 C7 H7 123.9 . . ? N5 C8 C1 113.8(5) . . ? N5 C8 H8A 108.8 . . ? C1 C8 H8A 108.8 . . ? N5 C8 H8AB 108.8 . . ? C1 C8 H8AB 108.8 . . ? H8A C8 H8AB 107.7 . . ? C22 N21 N22 111.4(5) . . ? C22 N21 C21 128.7(5) . . ? N22 N21 C21 119.9(5) . . ? N23 C21 N21 109.3(5) . . ? N23 C21 C28 112.7(5) . . ? N21 C21 C28 111.6(5) . . ? N23 C21 H21 107.7 . . ? N21 C21 H21 107.7 . . ? C28 C21 H21 107.7 . . ? C24 N22 N21 104.3(5) . . ? C24 N22 Cu3 136.5(4) . . ? N21 N22 Cu3 117.9(4) . . ? N21 C22 C23 107.9(6) . . ? N21 C22 H22 126.1 . . ? C23 C22 H22 126.1 . . ? C25 N23 N24 111.1(5) . . ? C25 N23 C21 128.3(5) . . ? N24 N23 C21 120.1(5) . . ? C22 C23 C24 104.2(5) . . ? C22 C23 H23 127.9 . . ? C24 C23 H23 127.9 . . ? C27 N24 N23 105.1(5) . . ? C27 N24 Cu3 139.8(5) . . ? N23 N24 Cu3 113.9(4) . . ? N22 C24 C23 112.2(6) . . ? N22 C24 H24 123.9 . . ? C23 C24 H24 123.9 . . ? C28 N25 Cu3 119.4(4) . . ? C28 N25 H102 107(5) . . ? Cu3 N25 H102 103(5) . . ? C28 N25 H103 107(5) . . ? Cu3 N25 H103 109(5) . . ? H102 N25 H103 111(7) . . ? N23 C25 C26 107.1(6) . . ? N23 C25 H25 126.5 . . ? C26 C25 H25 126.5 . . ? C25 C26 C27 105.6(6) . . ? C25 C26 H26 127.2 . . ? C27 C26 H26 127.2 . . ? N24 C27 C26 111.1(6) . . ? N24 C27 H27 124.5 . . ? C26 C27 H27 124.5 . . ? N25 C28 C21 113.5(5) . . ? N25 C28 H28A 108.9 . . ? C21 C28 H28A 108.9 . . ? N25 C28 H28B 108.9 . . ? C21 C28 H28B 108.9 . . ? H28A C28 H28B 107.7 . . ? 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 Cu2 2.2890(19) . ? O1 H105 0.86(11) . ? O1 H104 0.77(8) . ? N1 C2 1.345(8) . ? N1 N2 1.378(7) . ? N1 C1 1.457(8) . ? C1 N3 1.449(8) . ? C1 C8 1.528(9) . ? C1 H1 1.0000 . ? Cu2 N5 2.028(5) . ? Cu2 N2 2.053(6) . ? Cu2 N4 2.205(6) . ? Cu2 Cl2 2.2924(17) . ? N2 C4 1.328(8) . ? C2 C3 1.381(9) . ? C2 H2 0.9500 . ? Cu3 N25 2.022(5) . ? Cu3 N22 2.052(5) . ? Cu3 N24 2.244(6) . ? Cu3 Cl3 2.2719(19) . ? Cu3 Cl4 2.2735(19) . ? N3 N4 1.360(7) . ? N3 C5 1.362(9) . ? C3 C4 1.389(9) . ? C3 H3 0.9500 . ? N4 C7 1.320(9) . ? C4 H4 0.9500 . ? N5 C8 1.480(8) . ? N5 H100 0.84(8) . ? N5 H101 0.99(9) . ? C5 C6 1.359(10) . ? C5 H5 0.9500 . ? C6 C7 1.368(10) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9900 . ? C8 H8AB 0.9900 . ? N21 C22 1.343(8) . ? N21 N22 1.360(7) . ? N21 C21 1.463(8) . ? C21 N23 1.451(8) . ? C21 C28 1.523(9) . ? C21 H21 1.0000 . ? N22 C24 1.337(8) . ? C22 C23 1.375(9) . ? C22 H22 0.9500 . ? N23 C25 1.356(8) . ? N23 N24 1.370(7) . ? C23 C24 1.387(9) . ? C23 H23 0.9500 . ? N24 C27 1.328(9) . ? C24 H24 0.9500 . ? N25 C28 1.477(8) . ? N25 H102 0.87(2) . ? N25 H103 0.88(2) . ? C25 C26 1.366(10) . ? C25 H25 0.9500 . ? C26 C27 1.401(10) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? 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 _geom_hbond_publ_flag O1 H105 Cl4 0.86(11) 2.41(11) 3.251(6) 163(9) 1_665 yes C1 H1 Cl1 1.00 2.61 3.431(6) 139.2 1_655 yes C2 H2 Cl2 0.95 2.78 3.561(7) 140.5 1_655 yes C21 H21 Cl3 1.00 2.71 3.486(6) 134.4 1_655 yes C21 H21 Cl4 1.00 2.71 3.603(7) 148.7 1_655 yes C22 H22 Cl4 0.95 2.78 3.559(7) 140.0 1_655 yes N5 H100 Cl3 0.84(8) 2.59(8) 3.344(6) 150(6) 2_566 yes N5 H101 O1 0.99(9) 2.04(9) 3.002(8) 162(7) . yes N25 H102 Cl1 0.87(2) 2.58(3) 3.419(5) 163(6) 2_566 yes N25 H103 Cl1 0.88(2) 2.52(3) 3.355(6) 159(6) . yes O1 H104 Cl2 0.77(8) 2.51(8) 3.269(6) 167(7) 2_677 yes 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 C2 N1 C1 N3 104.9(7) . . . . ? N2 N1 C1 N3 -68.6(7) . . . . ? C2 N1 C1 C8 -129.1(7) . . . . ? N2 N1 C1 C8 57.4(7) . . . . ? C2 N1 N2 C4 2.1(7) . . . . ? C1 N1 N2 C4 176.7(5) . . . . ? C2 N1 N2 Cu2 -168.5(4) . . . . ? C1 N1 N2 Cu2 6.1(7) . . . . ? N2 N1 C2 C3 -2.7(7) . . . . ? C1 N1 C2 C3 -176.7(6) . . . . ? N1 C1 N3 N4 64.3(7) . . . . ? C8 C1 N3 N4 -61.3(7) . . . . ? N1 C1 N3 C5 -107.3(7) . . . . ? C8 C1 N3 C5 127.0(7) . . . . ? N1 C2 C3 C4 2.1(7) . . . . ? C5 N3 N4 C7 0.2(7) . . . . ? C1 N3 N4 C7 -172.8(5) . . . . ? C5 N3 N4 Cu2 169.8(4) . . . . ? C1 N3 N4 Cu2 -3.2(7) . . . . ? N1 N2 C4 C3 -0.8(7) . . . . ? Cu2 N2 C4 C3 166.9(5) . . . . ? C2 C3 C4 N2 -0.8(8) . . . . ? N4 N3 C5 C6 -0.2(7) . . . . ? C1 N3 C5 C6 172.0(6) . . . . ? N3 C5 C6 C7 0.0(7) . . . . ? N3 N4 C7 C6 -0.3(7) . . . . ? Cu2 N4 C7 C6 -165.7(5) . . . . ? C5 C6 C7 N4 0.2(8) . . . . ? Cu2 N5 C8 C1 -12.8(8) . . . . ? N3 C1 C8 N5 72.2(7) . . . . ? N1 C1 C8 N5 -52.1(7) . . . . ? C22 N21 C21 N23 107.7(7) . . . . ? N22 N21 C21 N23 -72.1(7) . . . . ? C22 N21 C21 C28 -126.9(7) . . . . ? N22 N21 C21 C28 53.3(7) . . . . ? C22 N21 N22 C24 1.4(7) . . . . ? C21 N21 N22 C24 -178.7(5) . . . . ? C22 N21 N22 Cu3 -167.6(4) . . . . ? C21 N21 N22 Cu3 12.2(7) . . . . ? N22 N21 C22 C23 -1.5(7) . . . . ? C21 N21 C22 C23 178.7(6) . . . . ? N21 C21 N23 C25 -107.1(7) . . . . ? C28 C21 N23 C25 128.2(7) . . . . ? N21 C21 N23 N24 64.5(7) . . . . ? C28 C21 N23 N24 -60.3(7) . . . . ? N21 C22 C23 C24 0.9(7) . . . . ? C25 N23 N24 C27 -2.0(7) . . . . ? C21 N23 N24 C27 -174.9(6) . . . . ? C25 N23 N24 Cu3 168.4(4) . . . . ? C21 N23 N24 Cu3 -4.5(7) . . . . ? N21 N22 C24 C23 -0.8(7) . . . . ? Cu3 N22 C24 C23 165.0(5) . . . . ? C22 C23 C24 N22 0.0(8) . . . . ? N24 N23 C25 C26 2.4(8) . . . . ? C21 N23 C25 C26 174.5(6) . . . . ? N23 C25 C26 C27 -1.7(8) . . . . ? N23 N24 C27 C26 0.9(7) . . . . ? Cu3 N24 C27 C26 -165.4(5) . . . . ? C25 C26 C27 N24 0.5(8) . . . . ? Cu3 N25 C28 C21 11.0(7) . . . . ? N23 C21 C28 N25 57.9(7) . . . . ? N21 C21 C28 N25 -65.5(7) . . . . ?