#------------------------------------------------------------------------------ #$Date: 2021-07-31 04:52:40 +0300 (Sat, 31 Jul 2021) $ #$Revision: 267842 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/42/1564277.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_1564277 loop_ _publ_author_name 'Eagling, Louise' 'Leonard, Daniel J.' 'Schwarz, Maria' 'Urruzuno, I\~naki' 'Boden, Grace' 'Wailes, J. Steven' 'Ward, John W.' 'Clayden, Jonathan' _publ_section_title ; ‘Reverse biomimetic’ synthesis of l-arogenate and its stabilized analogues from l-tyrosine ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D1SC03554A _journal_year 2021 _chemical_absolute_configuration ad _chemical_formula_moiety 'C16 H21 Cl N2 O3' _chemical_formula_sum 'C16 H21 Cl N2 O3' _chemical_formula_weight 324.80 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2018-06-07 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-03-12 deposited with the CCDC. 2021-07-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.8233(2) _cell_length_b 11.9161(3) _cell_length_c 12.3076(3) _cell_measurement_reflns_used 4257 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 27.79 _cell_measurement_theta_min 2.38 _cell_volume 1587.33(6) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_collection 'Bruker Apex suite' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'Bruker area detector' _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device 'Bruker Apex II kappa CCD area detector' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_unetI/netI 0.0362 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 14647 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.906 _diffrn_reflns_theta_min 2.379 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.255 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.5591 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0755 before and 0.0460 after correction. The Ratio of minimum to maximum transmission is 0.7499. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.359 _exptl_crystal_description block _exptl_crystal_F_000 688 _exptl_crystal_size_max 0.426 _exptl_crystal_size_mid 0.396 _exptl_crystal_size_min 0.166 _refine_diff_density_max 0.218 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.042 _refine_ls_abs_structure_details ; Flack x determined using 1410 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 207 _refine_ls_number_reflns 3800 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0347 _refine_ls_R_factor_gt 0.0298 _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^)+(0.0351P)^2^+0.1478P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.0691 _reflns_Friedel_coverage 0.753 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.997 _reflns_number_gt 3478 _reflns_number_total 3800 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc03554a2.cif _cod_data_source_block testo1 _cod_database_code 1564277 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C3(H3), C1(H1) 2.b Secondary CH2 refined with riding coordinates: C4(H4A,H4B) 2.c Aromatic/amide H refined with riding coordinates: C6(H6), C7(H7), C10(H10), C9(H9) 2.d Idealised Me refined as rotating group: C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C14(H14A,H14B, H14C) ; _shelx_res_file ; TITL testo1_a.res in P2(1)2(1)2(1) testo1.res created by SHELXL-2017/1 at 14:43:58 on 07-Jun-2018 REM Old TITL testo1 in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.075, Rweak 0.021, Alpha 0.001, Orientation as input REM Flack x = 0.030 ( 0.026 ) from Parsons' quotients REM Formula found by SHELXT: C16 N2 O3 Cl CELL 0.71073 10.8233 11.9161 12.3076 90 90 90 ZERR 4 0.0002 0.0003 0.0003 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H Cl N O UNIT 64 84 4 8 12 EQIV $1 1-X,0.5+Y,0.5-Z L.S. 4 0 0 PLAN 5 TEMP -173.15 HTAB O2 O1_$1 BOND $H CONF list 4 fmap 2 53 acta REM REM REM WGHT 0.035100 0.147800 FVAR 0.82566 CL1 3 0.278355 0.747652 0.571782 11.00000 0.01520 0.01490 = 0.02497 0.00002 -0.00003 0.00492 O2 5 0.530555 0.590116 0.046745 11.00000 0.02207 0.01437 = 0.01522 0.00137 0.00443 -0.00119 O1 5 0.399855 0.304243 0.497240 11.00000 0.01809 0.01254 = 0.01493 -0.00068 -0.00084 -0.00168 O3 5 0.514037 0.764304 0.540949 11.00000 0.01789 0.01481 = 0.01876 0.00237 0.00237 -0.00371 N2 4 0.443098 0.586534 0.567958 11.00000 0.00999 0.01158 = 0.01324 -0.00051 -0.00079 0.00012 N1 4 0.553587 0.426614 0.545206 11.00000 0.01112 0.01169 = 0.01315 -0.00225 0.00027 0.00229 C6 1 0.375587 0.446323 0.268839 11.00000 0.01291 0.01189 = 0.01671 0.00152 -0.00281 -0.00192 AFIX 43 H6 2 0.354990 0.371501 0.288384 11.00000 -1.20000 AFIX 0 C2 1 0.436495 0.397174 0.527349 11.00000 0.01461 0.01533 = 0.00732 0.00232 0.00079 0.00138 C8 1 0.470539 0.574658 0.143381 11.00000 0.00964 0.01876 = 0.01175 0.00199 -0.00242 -0.00037 C4 1 0.271113 0.512642 0.441759 11.00000 0.01069 0.01559 = 0.01238 -0.00035 -0.00068 0.00018 AFIX 23 H4A 2 0.220205 0.444351 0.432039 11.00000 -1.20000 H4B 2 0.214036 0.576257 0.454308 11.00000 -1.20000 AFIX 0 C5 1 0.341576 0.534091 0.337755 11.00000 0.01018 0.01647 = 0.01200 0.00193 -0.00384 0.00056 C3 1 0.352029 0.497369 0.543895 11.00000 0.01200 0.01084 = 0.01166 0.00084 0.00055 -0.00063 AFIX 13 H3 2 0.298215 0.484556 0.608766 11.00000 -1.20000 AFIX 0 C7 1 0.438885 0.465665 0.172260 11.00000 0.01264 0.01570 = 0.01481 -0.00297 -0.00314 0.00231 AFIX 43 H7 2 0.460356 0.404663 0.126290 11.00000 -1.20000 AFIX 0 C11 1 0.602271 0.543264 0.711823 11.00000 0.01307 0.01435 = 0.01174 -0.00077 -0.00166 0.00108 C1 1 0.568021 0.540059 0.588718 11.00000 0.00916 0.01163 = 0.01339 -0.00034 0.00088 0.00107 AFIX 13 H1 2 0.631010 0.582207 0.545496 11.00000 -1.20000 AFIX 0 C10 1 0.374027 0.642643 0.306393 11.00000 0.02093 0.01481 = 0.01431 0.00102 -0.00199 0.00290 AFIX 43 H10 2 0.351227 0.704015 0.351396 11.00000 -1.20000 AFIX 0 C16 1 0.433024 0.697794 0.555553 11.00000 0.01451 0.01601 = 0.01091 0.00115 -0.00039 0.00422 C9 1 0.438835 0.663321 0.211034 11.00000 0.02041 0.01183 = 0.01580 0.00309 -0.00245 -0.00115 AFIX 43 H9 2 0.461377 0.737872 0.192190 11.00000 -1.20000 AFIX 0 C15 1 0.656858 0.349864 0.528463 11.00000 0.01580 0.01758 = 0.02247 -0.00555 0.00014 0.00590 AFIX 137 H15A 2 0.665668 0.301102 0.592114 11.00000 -1.50000 H15B 2 0.733003 0.393066 0.518134 11.00000 -1.50000 H15C 2 0.641276 0.303865 0.463895 11.00000 -1.50000 AFIX 0 C13 1 0.519124 0.464196 0.776651 11.00000 0.02624 0.01948 = 0.01298 0.00253 0.00002 -0.00318 AFIX 137 H13A 2 0.432460 0.484790 0.765061 11.00000 -1.50000 H13B 2 0.539006 0.470247 0.854112 11.00000 -1.50000 H13C 2 0.532573 0.386832 0.752364 11.00000 -1.50000 AFIX 0 C12 1 0.587870 0.662265 0.756360 11.00000 0.02404 0.01691 = 0.01637 -0.00553 -0.00379 -0.00115 AFIX 137 H12A 2 0.637458 0.714207 0.712661 11.00000 -1.50000 H12B 2 0.616153 0.664445 0.831972 11.00000 -1.50000 H12C 2 0.500766 0.684452 0.753006 11.00000 -1.50000 AFIX 0 C14 1 0.738730 0.510325 0.725438 11.00000 0.01782 0.03059 = 0.02058 -0.00559 -0.00644 0.00590 AFIX 137 H14A 2 0.749273 0.430879 0.707061 11.00000 -1.50000 H14B 2 0.764075 0.522855 0.800912 11.00000 -1.50000 H14C 2 0.789829 0.556246 0.677020 11.00000 -1.50000 AFIX 0 H2 2 0.544537 0.661947 0.039742 11.00000 0.02812 HKLF 4 REM testo1_a.res in P2(1)2(1)2(1) REM R1 = 0.0298 for 3478 Fo > 4sig(Fo) and 0.0347 for all 3800 data REM 207 parameters refined using 0 restraints END WGHT 0.0351 0.1478 REM Highest difference peak 0.218, deepest hole -0.210, 1-sigma level 0.042 Q1 1 0.3827 0.4404 0.5458 11.00000 0.05 0.22 Q2 1 0.5758 0.5396 0.6553 11.00000 0.05 0.21 Q3 1 0.5626 0.4797 0.5594 11.00000 0.05 0.21 Q4 1 0.3871 0.5524 0.5627 11.00000 0.05 0.20 Q5 1 0.3302 0.5170 0.4837 11.00000 0.05 0.19 ; _shelx_res_checksum 46749 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -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 0.27835(4) 0.74765(4) 0.57178(4) 0.01836(12) Uani 1 1 d . . . . . O2 O 0.53055(13) 0.59012(14) 0.04675(12) 0.0172(3) Uani 1 1 d . . . . . O1 O 0.39986(13) 0.30424(12) 0.49724(12) 0.0152(3) Uani 1 1 d . . . . . O3 O 0.51404(13) 0.76430(13) 0.54095(11) 0.0172(3) Uani 1 1 d . . . . . N2 N 0.44310(14) 0.58653(14) 0.56796(14) 0.0116(3) Uani 1 1 d . . . . . N1 N 0.55359(15) 0.42661(14) 0.54521(13) 0.0120(4) Uani 1 1 d . . . . . C6 C 0.37559(18) 0.44632(18) 0.26884(17) 0.0138(4) Uani 1 1 d . . . . . H6 H 0.354990 0.371501 0.288384 0.017 Uiso 1 1 calc R . . . . C2 C 0.43649(19) 0.39717(18) 0.52735(16) 0.0124(4) Uani 1 1 d . . . . . C8 C 0.47054(17) 0.57466(19) 0.14338(16) 0.0134(4) Uani 1 1 d . . . . . C4 C 0.27111(18) 0.51264(17) 0.44176(15) 0.0129(4) Uani 1 1 d . . . . . H4A H 0.220205 0.444351 0.432039 0.015 Uiso 1 1 calc R . . . . H4B H 0.214036 0.576257 0.454308 0.015 Uiso 1 1 calc R . . . . C5 C 0.34158(17) 0.53409(19) 0.33776(16) 0.0129(4) Uani 1 1 d . . . . . C3 C 0.35203(17) 0.49737(17) 0.54389(16) 0.0115(4) Uani 1 1 d . . . . . H3 H 0.298215 0.484556 0.608766 0.014 Uiso 1 1 calc R . . . . C7 C 0.43888(18) 0.46566(19) 0.17226(16) 0.0144(4) Uani 1 1 d . . . . . H7 H 0.460356 0.404663 0.126290 0.017 Uiso 1 1 calc R . . . . C11 C 0.60227(18) 0.54326(18) 0.71182(17) 0.0131(4) Uani 1 1 d . . . . . C1 C 0.56802(17) 0.54006(17) 0.58872(15) 0.0114(4) Uani 1 1 d . . . . . H1 H 0.631010 0.582207 0.545496 0.014 Uiso 1 1 calc R . . . . C10 C 0.3740(2) 0.64264(19) 0.30639(17) 0.0167(4) Uani 1 1 d . . . . . H10 H 0.351227 0.704015 0.351396 0.020 Uiso 1 1 calc R . . . . C16 C 0.43302(19) 0.69779(18) 0.55555(16) 0.0138(4) Uani 1 1 d . . . . . C9 C 0.4388(2) 0.66332(18) 0.21103(17) 0.0160(4) Uani 1 1 d . . . . . H9 H 0.461377 0.737872 0.192190 0.019 Uiso 1 1 calc R . . . . C15 C 0.65686(19) 0.34986(19) 0.52846(19) 0.0186(5) Uani 1 1 d . . . . . H15A H 0.665668 0.301102 0.592114 0.028 Uiso 1 1 calc GR . . . . H15B H 0.733003 0.393066 0.518134 0.028 Uiso 1 1 calc GR . . . . H15C H 0.641276 0.303865 0.463895 0.028 Uiso 1 1 calc GR . . . . C13 C 0.5191(2) 0.4642(2) 0.77665(17) 0.0196(5) Uani 1 1 d . . . . . H13A H 0.432460 0.484790 0.765061 0.029 Uiso 1 1 calc GR . . . . H13B H 0.539006 0.470247 0.854112 0.029 Uiso 1 1 calc GR . . . . H13C H 0.532573 0.386832 0.752364 0.029 Uiso 1 1 calc GR . . . . C12 C 0.5879(2) 0.66226(19) 0.75636(18) 0.0191(5) Uani 1 1 d . . . . . H12A H 0.637458 0.714207 0.712661 0.029 Uiso 1 1 calc GR . . . . H12B H 0.616153 0.664445 0.831972 0.029 Uiso 1 1 calc GR . . . . H12C H 0.500766 0.684452 0.753006 0.029 Uiso 1 1 calc GR . . . . C14 C 0.7387(2) 0.5103(2) 0.72544(19) 0.0230(5) Uani 1 1 d . . . . . H14A H 0.749273 0.430879 0.707061 0.034 Uiso 1 1 calc GR . . . . H14B H 0.764075 0.522855 0.800912 0.034 Uiso 1 1 calc GR . . . . H14C H 0.789829 0.556246 0.677020 0.034 Uiso 1 1 calc GR . . . . H2 H 0.545(2) 0.662(2) 0.040(2) 0.028(8) 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 0.0152(2) 0.0149(2) 0.0250(2) 0.0000(2) -0.00003(19) 0.0049(2) O2 0.0221(8) 0.0144(8) 0.0152(8) 0.0014(6) 0.0044(6) -0.0012(6) O1 0.0181(7) 0.0125(7) 0.0149(7) -0.0007(6) -0.0008(6) -0.0017(6) O3 0.0179(7) 0.0148(8) 0.0188(7) 0.0024(6) 0.0024(6) -0.0037(6) N2 0.0100(7) 0.0116(8) 0.0132(8) -0.0005(7) -0.0008(7) 0.0001(6) N1 0.0111(8) 0.0117(9) 0.0131(8) -0.0022(7) 0.0003(6) 0.0023(6) C6 0.0129(9) 0.0119(11) 0.0167(10) 0.0015(8) -0.0028(8) -0.0019(8) C2 0.0146(9) 0.0153(11) 0.0073(9) 0.0023(8) 0.0008(8) 0.0014(8) C8 0.0096(9) 0.0188(12) 0.0118(9) 0.0020(8) -0.0024(7) -0.0004(8) C4 0.0107(8) 0.0156(10) 0.0124(9) -0.0003(8) -0.0007(8) 0.0002(8) C5 0.0102(9) 0.0165(11) 0.0120(9) 0.0019(8) -0.0038(7) 0.0006(8) C3 0.0120(9) 0.0108(10) 0.0117(10) 0.0008(7) 0.0005(7) -0.0006(7) C7 0.0126(9) 0.0157(11) 0.0148(10) -0.0030(8) -0.0031(8) 0.0023(8) C11 0.0131(9) 0.0143(10) 0.0117(9) -0.0008(8) -0.0017(7) 0.0011(8) C1 0.0092(8) 0.0116(9) 0.0134(9) -0.0003(8) 0.0009(7) 0.0011(7) C10 0.0209(11) 0.0148(11) 0.0143(10) 0.0010(9) -0.0020(8) 0.0029(9) C16 0.0145(9) 0.0160(10) 0.0109(9) 0.0011(8) -0.0004(8) 0.0042(8) C9 0.0204(11) 0.0118(11) 0.0158(10) 0.0031(8) -0.0024(8) -0.0011(8) C15 0.0158(10) 0.0176(11) 0.0225(11) -0.0056(9) 0.0001(8) 0.0059(9) C13 0.0262(11) 0.0195(12) 0.0130(10) 0.0025(9) 0.0000(8) -0.0032(9) C12 0.0240(11) 0.0169(12) 0.0164(11) -0.0055(9) -0.0038(9) -0.0012(9) C14 0.0178(11) 0.0306(14) 0.0206(11) -0.0056(10) -0.0064(9) 0.0059(9) 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' Cl Cl 0.1484 0.1585 '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' 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 C8 O2 H2 107.5(18) . . ? C3 N2 C1 111.94(16) . . ? C16 N2 C3 129.35(17) . . ? C16 N2 C1 117.62(16) . . ? C2 N1 C1 113.90(16) . . ? C2 N1 C15 122.69(18) . . ? C15 N1 C1 123.32(16) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C7 C6 C5 121.7(2) . . ? O1 C2 N1 126.26(19) . . ? O1 C2 C3 123.58(18) . . ? N1 C2 C3 110.09(17) . . ? O2 C8 C7 117.74(19) . . ? O2 C8 C9 122.4(2) . . ? C9 C8 C7 119.80(19) . . ? H4A C4 H4B 107.5 . . ? C5 C4 H4A 108.5 . . ? C5 C4 H4B 108.5 . . ? C5 C4 C3 115.05(15) . . ? C3 C4 H4A 108.5 . . ? C3 C4 H4B 108.5 . . ? C6 C5 C4 121.39(19) . . ? C10 C5 C6 117.40(19) . . ? C10 C5 C4 121.21(19) . . ? N2 C3 C2 100.99(15) . . ? N2 C3 C4 117.17(16) . . ? N2 C3 H3 109.7 . . ? C2 C3 C4 108.99(16) . . ? C2 C3 H3 109.7 . . ? C4 C3 H3 109.7 . . ? C6 C7 H7 120.2 . . ? C8 C7 C6 119.7(2) . . ? C8 C7 H7 120.2 . . ? C13 C11 C1 110.62(17) . . ? C13 C11 C12 108.95(18) . . ? C13 C11 C14 110.58(18) . . ? C12 C11 C1 110.29(17) . . ? C12 C11 C14 107.20(18) . . ? C14 C11 C1 109.14(16) . . ? N2 C1 C11 112.01(15) . . ? N2 C1 H1 110.0 . . ? N1 C1 N2 100.64(15) . . ? N1 C1 C11 113.80(17) . . ? N1 C1 H1 110.0 . . ? C11 C1 H1 110.0 . . ? C5 C10 H10 119.2 . . ? C9 C10 C5 121.7(2) . . ? C9 C10 H10 119.2 . . ? O3 C16 Cl1 118.90(16) . . ? O3 C16 N2 127.87(19) . . ? N2 C16 Cl1 113.12(15) . . ? C8 C9 C10 119.8(2) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 Cl1 C16 1.788(2) . ? O2 C8 1.368(2) . ? O2 H2 0.87(3) . ? O1 C2 1.233(3) . ? O3 C16 1.196(3) . ? N2 C3 1.479(3) . ? N2 C1 1.483(2) . ? N2 C16 1.339(3) . ? N1 C2 1.333(3) . ? N1 C1 1.462(3) . ? N1 C15 1.459(3) . ? C6 H6 0.9500 . ? C6 C5 1.396(3) . ? C6 C7 1.391(3) . ? C2 C3 1.517(3) . ? C8 C7 1.389(3) . ? C8 C9 1.388(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.512(3) . ? C4 C3 1.543(3) . ? C5 C10 1.395(3) . ? C3 H3 1.0000 . ? C7 H7 0.9500 . ? C11 C1 1.560(3) . ? C11 C13 1.528(3) . ? C11 C12 1.528(3) . ? C11 C14 1.537(3) . ? C1 H1 1.0000 . ? C10 H10 0.9500 . ? C10 C9 1.389(3) . ? C9 H9 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 O2 H2 O1 0.87(3) 1.86(3) 2.715(2) 167(3) 3_655 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 O2 C8 C7 C6 -178.73(17) . . . . ? O2 C8 C9 C10 177.73(18) . . . . ? O1 C2 C3 N2 -174.44(19) . . . . ? O1 C2 C3 C4 -50.5(3) . . . . ? N1 C2 C3 N2 2.8(2) . . . . ? N1 C2 C3 C4 126.73(17) . . . . ? C6 C5 C10 C9 -0.7(3) . . . . ? C2 N1 C1 N2 -14.1(2) . . . . ? C2 N1 C1 C11 105.88(19) . . . . ? C4 C5 C10 C9 179.96(19) . . . . ? C5 C6 C7 C8 0.6(3) . . . . ? C5 C4 C3 N2 53.3(2) . . . . ? C5 C4 C3 C2 -60.5(2) . . . . ? C5 C10 C9 C8 1.3(3) . . . . ? C3 N2 C1 N1 15.72(19) . . . . ? C3 N2 C1 C11 -105.53(19) . . . . ? C3 N2 C16 Cl1 30.6(3) . . . . ? C3 N2 C16 O3 -153.3(2) . . . . ? C3 C4 C5 C6 92.7(2) . . . . ? C3 C4 C5 C10 -88.0(2) . . . . ? C7 C6 C5 C4 179.07(18) . . . . ? C7 C6 C5 C10 -0.3(3) . . . . ? C7 C8 C9 C10 -1.0(3) . . . . ? C1 N2 C3 C2 -11.9(2) . . . . ? C1 N2 C3 C4 -130.07(17) . . . . ? C1 N2 C16 Cl1 -162.34(13) . . . . ? C1 N2 C16 O3 13.7(3) . . . . ? C1 N1 C2 O1 -175.40(19) . . . . ? C1 N1 C2 C3 7.5(2) . . . . ? C16 N2 C3 C2 155.7(2) . . . . ? C16 N2 C3 C4 37.5(3) . . . . ? C16 N2 C1 N1 -153.48(17) . . . . ? C16 N2 C1 C11 85.3(2) . . . . ? C9 C8 C7 C6 0.0(3) . . . . ? C15 N1 C2 O1 1.3(3) . . . . ? C15 N1 C2 C3 -175.78(18) . . . . ? C15 N1 C1 N2 169.21(17) . . . . ? C15 N1 C1 C11 -70.8(2) . . . . ? C13 C11 C1 N2 66.3(2) . . . . ? C13 C11 C1 N1 -47.0(2) . . . . ? C12 C11 C1 N2 -54.3(2) . . . . ? C12 C11 C1 N1 -167.62(16) . . . . ? C14 C11 C1 N2 -171.81(17) . . . . ? C14 C11 C1 N1 74.9(2) . . . . ?