#------------------------------------------------------------------------------ #$Date: 2020-11-06 14:15:47 +0200 (Fri, 06 Nov 2020) $ #$Revision: 258839 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/53/7705305.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_7705305 loop_ _publ_author_name 'Bakhonsky, Vladyslav V.' 'Pashenko, Aleksander A.' 'Becker, Jonathan' 'Hausmann, Heike' 'De Groot, Huub J. M.' 'Overkleeft, Herman S.' 'Fokin, Andrey A.' 'Schreiner, Peter R.' _publ_section_title ; Synthesis and antiproliferative activity of hindered, chiral 1,2-diaminodiamantane platinum(II) complexes. ; _journal_issue 40 _journal_name_full 'Dalton transactions (Cambridge, England : 2003)' _journal_page_first 14009 _journal_page_last 14016 _journal_paper_doi 10.1039/d0dt02391d _journal_volume 49 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_sum 'C15 H28 Cl2 N2 O' _chemical_formula_weight 323.29 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2017/1 _audit_update_record ; 2019-09-30 deposited with the CCDC. 2020-08-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.4679(15) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.7449(3) _cell_length_b 8.4127(3) _cell_length_c 9.7717(3) _cell_measurement_reflns_used 9978 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 52.12 _cell_measurement_theta_min 2.42 _cell_volume 800.35(5) _computing_cell_refinement 'SAINT 8.38A (Bruker-AXS, 2017)' _computing_data_collection 'APEX3 v2017.3-0 (Bruker-AXS, 2017)' _computing_data_reduction 'SAINT 8.38A (Bruker-AXS, 2017)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_solution 'SHELXT-2015 (Sheldrick, 2015)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker PHOTON100' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_unetI/netI 0.0157 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 272934 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 49.117 _diffrn_reflns_theta_min 2.890 _diffrn_source 'I\mS micro-focus sealed tube, multilayer optics' _exptl_absorpt_coefficient_mu 0.404 _exptl_absorpt_correction_T_max 0.7503 _exptl_absorpt_correction_T_min 0.6984 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 2009)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 348 _exptl_crystal_size_max 0.560 _exptl_crystal_size_mid 0.335 _exptl_crystal_size_min 0.260 _refine_diff_density_max 0.265 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.065 _refine_ls_abs_structure_details ; Flack x determined using 7059 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.004(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 203 _refine_ls_number_reflns 16136 _refine_ls_number_restraints 8 _refine_ls_restrained_S_all 1.079 _refine_ls_R_factor_all 0.0207 _refine_ls_R_factor_gt 0.0189 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0329P)^2^+0.0050P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.0516 _reflns_Friedel_coverage 0.921 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 15392 _reflns_number_total 16136 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02391d2.cif _cod_data_source_block D18099 _cod_depositor_comments 'Adding full bibliography for 7705304--7705305.cif.' _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7705305 _shelx_shelxl_version_number 2017/1 _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 0.805 _shelx_estimated_absorpt_t_max 0.902 _shelx_res_file ; TITL D18099 in P2(1) D18099.res created by SHELXL-2017/1 at 10:30:30 on 11-Aug-2018 CELL 0.71073 9.74490 8.41270 9.77170 90.0000 92.4679 90.0000 ZERR 2.00 0.00030 0.00030 0.00030 0.0000 0.0015 0.0000 LATT -1 SYMM -X, 0.5+Y, -Z SFAC C H N O CL UNIT 30 56 4 2 4 LIST 4 TEMP -173 SIZE 0.26 0.335 0.56 OMIT -5 0 3 ! outlier, Fo > Fc OMIT -1 0 3 ! outlier, Fo > Fc OMIT 2 0 5 ! outlier, Fo > Fc OMIT -8 0 3 ! outlier, Fo > Fc OMIT 6 0 6 ! outlier, Fo > Fc OMIT 2 0 1 ! outlier, Fo > Fc OMIT 6 0 8 ! outlier, Fo > Fc OMIT -1 -3 3 ! outlier, Fo > Fc OMIT 1 0 1 ! partly behind beamstop shadow OMIT 0 -1 1 ! partly behind beamstop shadow ACTA L.S. 10 BOND $H FMAP 2 PLAN 20 EQIV $1 -x+2, y-1/2, -z+1 EQIV $2 -x+2, y+1/2, -z+1 EQIV $3 -x+2, y-1/2, -z HTAB O1 Cl2_$1 HTAB N1 O1 HTAB N1 Cl1 HTAB N1 Cl1_$2 HTAB N2 Cl2 HTAB N2 Cl1_$2 HTAB N2 Cl2_$3 HTAB DFIX 0.91 N1 H1A N1 H1B N1 H1C N2 H2A N2 H2B N2 H2C DFIX 0.84 O1 H1 WGHT 0.032900 0.005000 FVAR 0.40841 CL1 5 0.828174 0.065871 0.578995 11.00000 0.00921 0.01204 = 0.01567 0.00387 -0.00101 -0.00001 CL2 5 0.930292 0.934190 0.064003 11.00000 0.01620 0.01042 = 0.01160 0.00110 0.00330 -0.00188 O1 4 0.906715 0.583768 0.682926 11.00000 0.01717 0.02974 = 0.01298 -0.00625 -0.00345 0.00750 H1 2 0.956501 0.528963 0.740958 11.00000 -1.50000 REM Q6 1 0.9599 0.5218 0.7469 11.00000 0.05 0.54 N1 3 0.881999 0.394074 0.441266 11.00000 0.00882 0.01068 = 0.00959 0.00191 -0.00150 -0.00025 H1A 2 0.865570 0.463204 0.517359 11.00000 -1.20000 H1B 2 0.868698 0.293146 0.470969 11.00000 -1.20000 H1C 2 0.961747 0.399249 0.413486 11.00000 -1.20000 REM Q2 1 0.8704 0.4650 0.5095 11.00000 0.05 0.60 REM Q4 1 0.8721 0.3049 0.4712 11.00000 0.05 0.59 REM Q5 1 0.9732 0.4196 0.4196 11.00000 0.05 0.57 N2 3 0.934614 0.595058 0.192638 11.00000 0.00782 0.01014 = 0.00921 0.00009 0.00149 -0.00083 H2A 2 0.940206 0.687706 0.156492 11.00000 -1.20000 H2B 2 1.000370 0.596068 0.259212 11.00000 -1.20000 H2C 2 0.953042 0.530470 0.129483 11.00000 -1.20000 REM Q1 1 0.9387 0.6970 0.1499 11.00000 0.05 0.63 REM Q3 1 1.0079 0.5935 0.2585 11.00000 0.05 0.59 REM Q7 1 0.9502 0.5251 0.1256 11.00000 0.05 0.49 C1 1 0.777757 0.413973 0.323689 11.00000 0.00706 0.00774 = 0.00785 0.00050 -0.00060 -0.00051 C2 1 0.794372 0.575271 0.249821 11.00000 0.00671 0.00800 = 0.00757 0.00067 0.00051 -0.00012 C3 1 0.686534 0.580505 0.128741 11.00000 0.00873 0.01305 = 0.00847 0.00219 -0.00076 0.00014 AFIX 13 H3 2 0.697770 0.681815 0.076877 11.00000 -1.20000 AFIX 0 C4 1 0.542242 0.577086 0.187383 11.00000 0.00762 0.01522 = 0.01200 0.00240 -0.00122 0.00118 AFIX 13 H4 2 0.471953 0.583608 0.109954 11.00000 -1.20000 AFIX 0 C5 1 0.524768 0.417827 0.262984 11.00000 0.00728 0.01412 = 0.01159 0.00038 -0.00061 -0.00207 AFIX 13 H5 2 0.430867 0.413710 0.300271 11.00000 -1.20000 AFIX 0 C6 1 0.632531 0.410761 0.382876 11.00000 0.00767 0.01026 = 0.00938 0.00100 0.00059 -0.00157 AFIX 13 H6 2 0.620998 0.308907 0.433871 11.00000 -1.20000 AFIX 0 C7 1 0.794630 0.273917 0.225754 11.00000 0.01083 0.00864 = 0.01233 -0.00204 -0.00024 -0.00013 AFIX 23 H7A 2 0.784964 0.172687 0.276095 11.00000 -1.20000 H7AB 2 0.887443 0.276732 0.188420 11.00000 -1.20000 AFIX 0 C8 1 0.685796 0.282600 0.108108 11.00000 0.01217 0.01422 = 0.01187 -0.00402 -0.00089 -0.00256 AFIX 13 H8 2 0.697532 0.191128 0.044314 11.00000 -1.20000 AFIX 0 C9 1 0.702384 0.439401 0.030640 11.00000 0.01184 0.01850 = 0.00813 -0.00106 -0.00109 -0.00180 AFIX 23 H9A 2 0.632046 0.446361 -0.045300 11.00000 -1.20000 H9AB 2 0.794094 0.443092 -0.009070 11.00000 -1.20000 AFIX 0 C10 1 0.542292 0.276734 0.166276 11.00000 0.01146 0.01624 = 0.01488 -0.00306 -0.00137 -0.00487 AFIX 23 H10A 2 0.471544 0.281256 0.090571 11.00000 -1.20000 H10B 2 0.530567 0.175903 0.216686 11.00000 -1.20000 AFIX 0 C11 1 0.773395 0.714861 0.348110 11.00000 0.00985 0.00825 = 0.01159 -0.00109 0.00195 -0.00038 AFIX 23 H11A 2 0.842882 0.709855 0.424936 11.00000 -1.20000 H11B 2 0.785483 0.816568 0.299110 11.00000 -1.20000 AFIX 0 C12 1 0.628768 0.707725 0.404125 11.00000 0.01049 0.01110 = 0.01368 -0.00138 0.00329 0.00131 AFIX 13 H12 2 0.615786 0.798658 0.468195 11.00000 -1.20000 AFIX 0 C13 1 0.522495 0.718028 0.284091 11.00000 0.01022 0.01437 = 0.01833 0.00198 0.00155 0.00411 AFIX 23 H13A 2 0.534062 0.819096 0.233987 11.00000 -1.20000 H13B 2 0.428622 0.715735 0.318954 11.00000 -1.20000 AFIX 0 C14 1 0.609513 0.550230 0.480120 11.00000 0.01016 0.01394 = 0.01004 -0.00085 0.00261 -0.00100 AFIX 23 H14A 2 0.675714 0.543861 0.559669 11.00000 -1.20000 H14B 2 0.515522 0.544870 0.514467 11.00000 -1.20000 AFIX 0 C15 1 0.818595 0.683482 0.757943 11.00000 0.01655 0.01649 = 0.01422 -0.00089 0.00093 0.00148 AFIX 137 H15A 2 0.788312 0.773454 0.700538 11.00000 -1.50000 H15B 2 0.868509 0.723120 0.840214 11.00000 -1.50000 H15C 2 0.738394 0.622413 0.784643 11.00000 -1.50000 AFIX 0 HKLF 4 REM D18099 in P2(1) REM R1 = 0.0189 for 15392 Fo > 4sig(Fo) and 0.0207 for all 16136 data REM 203 parameters refined using 8 restraints END WGHT 0.0329 0.0050 REM Instructions for potential hydrogen bonds HTAB O1 Cl2_$1 HTAB N1 O1 HTAB N1 Cl1 HTAB N1 Cl1_$2 HTAB N2 Cl2 HTAB N2 Cl1_$2 HTAB N2 Cl2_$3 HTAB C11 Cl2 EQIV $4 x, y+1, z HTAB C15 Cl1_$4 EQIV $5 x, y, z+1 HTAB C15 Cl2_$5 REM Highest difference peak 0.265, deepest hole -0.296, 1-sigma level 0.065 Q1 1 0.8397 0.1140 0.6127 11.00000 0.05 0.26 Q2 1 0.7598 0.2827 0.1805 11.00000 0.05 0.26 Q3 1 0.8786 0.5338 0.7043 11.00000 0.05 0.26 Q4 1 0.8600 0.0643 0.5364 11.00000 0.05 0.25 Q5 1 0.6159 0.6230 0.4419 11.00000 0.05 0.24 Q6 1 0.7514 0.5797 0.1963 11.00000 0.05 0.24 Q7 1 0.8412 0.9651 0.2420 11.00000 0.05 0.23 Q8 1 0.5382 0.5137 0.2211 11.00000 0.05 0.23 Q9 1 0.7101 0.7069 0.3788 11.00000 0.05 0.22 Q10 1 0.7833 0.3667 0.2825 11.00000 0.05 0.22 Q11 1 0.8590 0.9892 0.2789 11.00000 0.05 0.21 Q12 1 0.5884 0.7051 0.3530 11.00000 0.05 0.21 Q13 1 0.6157 0.2833 0.1476 11.00000 0.05 0.21 Q14 1 0.7482 0.8597 0.1681 11.00000 0.05 0.21 Q15 1 0.6178 0.4993 0.4358 11.00000 0.05 0.21 Q16 1 0.7666 0.7799 0.0416 11.00000 0.05 0.20 Q17 1 0.8591 0.0319 0.2489 11.00000 0.05 0.20 Q18 1 0.6888 0.3595 0.0825 11.00000 0.05 0.20 Q19 1 0.6158 0.5889 0.1578 11.00000 0.05 0.19 Q20 1 0.7252 0.4426 0.6265 11.00000 0.05 0.18 ; _shelx_res_checksum 43551 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -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 0.82817(2) 0.06587(2) 0.57900(2) 0.01235(2) Uani 1 1 d . . . . . Cl2 Cl 0.93029(2) 0.93419(2) 0.06400(2) 0.01266(2) Uani 1 1 d . . . . . O1 O 0.90671(5) 0.58377(7) 0.68293(4) 0.02008(8) Uani 1 1 d D . . . . H1 H 0.9565(13) 0.5290(18) 0.7410(14) 0.030 Uiso 1 1 d D U . . . N1 N 0.88200(4) 0.39407(5) 0.44127(4) 0.00975(5) Uani 1 1 d D . . . . H1A H 0.8656(11) 0.4632(13) 0.5174(10) 0.012 Uiso 1 1 d D U . . . H1B H 0.8687(11) 0.2931(13) 0.4710(10) 0.012 Uiso 1 1 d D U . . . H1C H 0.9617(10) 0.3992(14) 0.4135(10) 0.012 Uiso 1 1 d D U . . . N2 N 0.93461(3) 0.59506(4) 0.19264(4) 0.00902(4) Uani 1 1 d D . . . . H2A H 0.9402(11) 0.6877(13) 0.1565(10) 0.011 Uiso 1 1 d D U . . . H2B H 1.0004(10) 0.5961(14) 0.2592(10) 0.011 Uiso 1 1 d D U . . . H2C H 0.9530(10) 0.5305(13) 0.1295(10) 0.011 Uiso 1 1 d D U . . . C1 C 0.77776(4) 0.41397(4) 0.32369(4) 0.00758(5) Uani 1 1 d . . . . . C2 C 0.79437(4) 0.57527(5) 0.24982(4) 0.00742(4) Uani 1 1 d . . . . . C3 C 0.68653(4) 0.58051(5) 0.12874(4) 0.01011(5) Uani 1 1 d . . . . . H3 H 0.697770 0.681815 0.076877 0.012 Uiso 1 1 calc R U . . . C4 C 0.54224(4) 0.57709(6) 0.18738(4) 0.01166(6) Uani 1 1 d . . . . . H4 H 0.471953 0.583608 0.109954 0.014 Uiso 1 1 calc R U . . . C5 C 0.52477(4) 0.41783(5) 0.26298(4) 0.01103(6) Uani 1 1 d . . . . . H5 H 0.430867 0.413710 0.300271 0.013 Uiso 1 1 calc R U . . . C6 C 0.63253(4) 0.41076(5) 0.38288(4) 0.00910(5) Uani 1 1 d . . . . . H6 H 0.620998 0.308907 0.433871 0.011 Uiso 1 1 calc R U . . . C7 C 0.79463(4) 0.27392(5) 0.22575(5) 0.01062(5) Uani 1 1 d . . . . . H7A H 0.784964 0.172687 0.276095 0.013 Uiso 1 1 calc R U . . . H7AB H 0.887443 0.276732 0.188420 0.013 Uiso 1 1 calc R U . . . C8 C 0.68580(5) 0.28260(6) 0.10811(5) 0.01279(6) Uani 1 1 d . . . . . H8 H 0.697532 0.191128 0.044314 0.015 Uiso 1 1 calc R U . . . C9 C 0.70238(4) 0.43940(7) 0.03064(4) 0.01287(6) Uani 1 1 d . . . . . H9A H 0.632046 0.446361 -0.045300 0.015 Uiso 1 1 calc R U . . . H9AB H 0.794094 0.443092 -0.009070 0.015 Uiso 1 1 calc R U . . . C10 C 0.54229(5) 0.27673(6) 0.16628(5) 0.01425(7) Uani 1 1 d . . . . . H10A H 0.471544 0.281256 0.090571 0.017 Uiso 1 1 calc R U . . . H10B H 0.530567 0.175903 0.216686 0.017 Uiso 1 1 calc R U . . . C11 C 0.77340(4) 0.71486(5) 0.34811(4) 0.00985(5) Uani 1 1 d . . . . . H11A H 0.842882 0.709855 0.424936 0.012 Uiso 1 1 calc R U . . . H11B H 0.785483 0.816568 0.299110 0.012 Uiso 1 1 calc R U . . . C12 C 0.62877(4) 0.70772(5) 0.40413(5) 0.01168(6) Uani 1 1 d . . . . . H12 H 0.615786 0.798658 0.468195 0.014 Uiso 1 1 calc R U . . . C13 C 0.52250(5) 0.71803(6) 0.28409(5) 0.01428(7) Uani 1 1 d . . . . . H13A H 0.534062 0.819096 0.233987 0.017 Uiso 1 1 calc R U . . . H13B H 0.428622 0.715735 0.318954 0.017 Uiso 1 1 calc R U . . . C14 C 0.60951(4) 0.55023(5) 0.48012(4) 0.01132(6) Uani 1 1 d . . . . . H14A H 0.675714 0.543861 0.559669 0.014 Uiso 1 1 calc R U . . . H14B H 0.515522 0.544870 0.514467 0.014 Uiso 1 1 calc R U . . . C15 C 0.81860(6) 0.68348(7) 0.75794(5) 0.01575(7) Uani 1 1 d . . . . . H15A H 0.788312 0.773454 0.700538 0.024 Uiso 1 1 calc R U . . . H15B H 0.868509 0.723120 0.840214 0.024 Uiso 1 1 calc R U . . . H15C H 0.738394 0.622413 0.784643 0.024 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 0.00921(3) 0.01204(3) 0.01567(4) 0.00387(3) -0.00101(3) -0.00001(3) Cl2 0.01620(4) 0.01042(3) 0.01160(3) 0.00110(3) 0.00330(3) -0.00188(3) O1 0.01717(14) 0.0297(2) 0.01298(12) -0.00625(13) -0.00345(10) 0.00750(14) N1 0.00882(10) 0.01068(11) 0.00959(11) 0.00191(9) -0.00150(8) -0.00025(9) N2 0.00782(10) 0.01014(11) 0.00921(10) 0.00009(8) 0.00149(8) -0.00083(8) C1 0.00706(10) 0.00774(12) 0.00785(10) 0.00050(8) -0.00060(8) -0.00051(8) C2 0.00671(9) 0.00800(11) 0.00757(10) 0.00067(9) 0.00051(8) -0.00012(9) C3 0.00873(11) 0.01305(14) 0.00847(11) 0.00219(10) -0.00076(9) 0.00014(10) C4 0.00762(11) 0.01522(15) 0.01200(13) 0.00240(12) -0.00122(9) 0.00118(11) C5 0.00728(11) 0.01412(15) 0.01159(13) 0.00038(11) -0.00061(9) -0.00207(11) C6 0.00767(11) 0.01026(13) 0.00938(11) 0.00100(9) 0.00059(9) -0.00157(9) C7 0.01083(13) 0.00864(12) 0.01233(13) -0.00204(10) -0.00024(10) -0.00013(10) C8 0.01217(14) 0.01422(15) 0.01187(14) -0.00402(11) -0.00089(11) -0.00256(12) C9 0.01184(13) 0.01850(16) 0.00813(11) -0.00106(12) -0.00109(10) -0.00180(13) C10 0.01146(14) 0.01624(16) 0.01488(16) -0.00306(13) -0.00137(12) -0.00487(12) C11 0.00985(12) 0.00825(12) 0.01159(13) -0.00109(10) 0.00195(10) -0.00038(10) C12 0.01049(13) 0.01110(13) 0.01368(14) -0.00138(11) 0.00329(11) 0.00131(11) C13 0.01022(14) 0.01437(15) 0.01833(17) 0.00198(13) 0.00155(12) 0.00411(12) C14 0.01016(12) 0.01394(15) 0.01004(12) -0.00085(10) 0.00261(10) -0.00100(11) C15 0.01655(17) 0.01649(17) 0.01422(16) -0.00089(13) 0.00093(13) 0.00148(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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 O1 H1 108.1(9) . . ? C1 N1 H1A 113.1(6) . . ? C1 N1 H1B 104.3(6) . . ? H1A N1 H1B 106.7(9) . . ? C1 N1 H1C 110.6(7) . . ? H1A N1 H1C 114.0(10) . . ? H1B N1 H1C 107.5(10) . . ? C2 N2 H2A 109.1(7) . . ? C2 N2 H2B 111.4(7) . . ? H2A N2 H2B 103.6(10) . . ? C2 N2 H2C 115.0(7) . . ? H2A N2 H2C 105.3(10) . . ? H2B N2 H2C 111.6(10) . . ? N1 C1 C7 107.66(3) . . ? N1 C1 C2 111.80(3) . . ? C7 C1 C2 111.51(3) . . ? N1 C1 C6 108.00(3) . . ? C7 C1 C6 110.10(3) . . ? C2 C1 C6 107.71(3) . . ? N2 C2 C11 107.12(3) . . ? N2 C2 C1 112.59(3) . . ? C11 C2 C1 111.04(3) . . ? N2 C2 C3 108.04(3) . . ? C11 C2 C3 110.59(3) . . ? C1 C2 C3 107.45(3) . . ? C9 C3 C4 109.58(4) . . ? C9 C3 C2 111.79(3) . . ? C4 C3 C2 108.38(3) . . ? C9 C3 H3 109.0 . . ? C4 C3 H3 109.0 . . ? C2 C3 H3 109.0 . . ? C13 C4 C3 110.82(4) . . ? C13 C4 C5 110.92(4) . . ? C3 C4 C5 108.39(3) . . ? C13 C4 H4 108.9 . . ? C3 C4 H4 108.9 . . ? C5 C4 H4 108.9 . . ? C10 C5 C6 110.42(4) . . ? C10 C5 C4 111.10(4) . . ? C6 C5 C4 108.18(3) . . ? C10 C5 H5 109.0 . . ? C6 C5 H5 109.0 . . ? C4 C5 H5 109.0 . . ? C14 C6 C5 109.20(3) . . ? C14 C6 C1 112.21(3) . . ? C5 C6 C1 108.58(3) . . ? C14 C6 H6 108.9 . . ? C5 C6 H6 108.9 . . ? C1 C6 H6 108.9 . . ? C1 C7 C8 110.05(3) . . ? C1 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? C1 C7 H7AB 109.7 . . ? C8 C7 H7AB 109.7 . . ? H7A C7 H7AB 108.2 . . ? C7 C8 C10 109.47(4) . . ? C7 C8 C9 109.11(4) . . ? C10 C8 C9 109.15(4) . . ? C7 C8 H8 109.7 . . ? C10 C8 H8 109.7 . . ? C9 C8 H8 109.7 . . ? C8 C9 C3 109.93(3) . . ? C8 C9 H9A 109.7 . . ? C3 C9 H9A 109.7 . . ? C8 C9 H9AB 109.7 . . ? C3 C9 H9AB 109.7 . . ? H9A C9 H9AB 108.2 . . ? C5 C10 C8 109.37(4) . . ? C5 C10 H10A 109.8 . . ? C8 C10 H10A 109.8 . . ? C5 C10 H10B 109.8 . . ? C8 C10 H10B 109.8 . . ? H10A C10 H10B 108.2 . . ? C12 C11 C2 110.00(3) . . ? C12 C11 H11A 109.7 . . ? C2 C11 H11A 109.7 . . ? C12 C11 H11B 109.7 . . ? C2 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C13 C12 C14 109.05(4) . . ? C13 C12 C11 108.98(4) . . ? C14 C12 C11 109.86(3) . . ? C13 C12 H12 109.6 . . ? C14 C12 H12 109.6 . . ? C11 C12 H12 109.6 . . ? C12 C13 C4 109.22(3) . . ? C12 C13 H13A 109.8 . . ? C4 C13 H13A 109.8 . . ? C12 C13 H13B 109.8 . . ? C4 C13 H13B 109.8 . . ? H13A C13 H13B 108.3 . . ? C6 C14 C12 109.68(3) . . ? C6 C14 H14A 109.7 . . ? C12 C14 H14A 109.7 . . ? C6 C14 H14B 109.7 . . ? C12 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? O1 C15 H15A 109.5 . . ? O1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C15 1.4257(7) . ? O1 H1 0.864(13) . ? N1 C1 1.5098(5) . ? N1 H1A 0.963(10) . ? N1 H1B 0.908(11) . ? N1 H1C 0.835(10) . ? N2 C2 1.5078(5) . ? N2 H2A 0.858(10) . ? N2 H2B 0.893(10) . ? N2 H2C 0.847(10) . ? C1 C7 1.5312(5) . ? C1 C2 1.5487(5) . ? C1 C6 1.5519(5) . ? C2 C11 1.5363(6) . ? C2 C3 1.5489(5) . ? C3 C9 1.5377(7) . ? C3 C4 1.5413(6) . ? C3 H3 1.0000 . ? C4 C13 1.5335(7) . ? C4 C5 1.5429(6) . ? C4 H4 1.0000 . ? C5 C10 1.5313(7) . ? C5 C6 1.5404(6) . ? C5 H5 1.0000 . ? C6 C14 1.5324(6) . ? C6 H6 1.0000 . ? C7 C8 1.5319(6) . ? C7 H7A 0.9900 . ? C7 H7AB 0.9900 . ? C8 C10 1.5328(7) . ? C8 C9 1.5329(7) . ? C8 H8 1.0000 . ? C9 H9A 0.9900 . ? C9 H9AB 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5349(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.5334(7) . ? C12 C14 1.5343(6) . ? C12 H12 1.0000 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 H1 Cl2 0.864(13) 2.303(13) 3.1438(4) 164.5(13) 2_746 yes N1 H1A O1 0.963(10) 1.937(10) 2.8517(6) 157.8(9) . yes N1 H1B Cl1 0.908(11) 2.228(11) 3.1258(4) 169.8(9) . yes N1 H1C Cl1 0.835(10) 2.480(10) 3.1864(4) 143.0(10) 2_756 yes N2 H2A Cl2 0.858(10) 2.262(10) 3.1172(4) 173.8(10) . yes N2 H2B Cl1 0.893(10) 2.265(10) 3.1527(4) 172.7(10) 2_756 yes N2 H2C Cl2 0.847(10) 2.389(10) 3.1840(4) 156.5(9) 2_745 yes