#------------------------------------------------------------------------------ #$Date: 2022-01-06 23:48:02 +0200 (Thu, 06 Jan 2022) $ #$Revision: 271866 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061070.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_7061070 loop_ _publ_author_name 'Dayaker, Gandrath' 'Erb, William' 'Hedidi, Madani' 'Chevallier, Floris' 'Blot, Marielle' 'Gros, Philippe C.' 'Hilmersson, G\"oran' 'Roisnel, Thierry' 'Dorcet, Vincent' 'Bentabed-Ababsa, Ghenia' 'Mongin, Florence' _publ_section_title ; Enantioselective deprotometalation of alkyl ferrocenecarboxylates using bimetallic bases ; _journal_issue 48 _journal_name_full 'New Journal of Chemistry' _journal_page_first 22579 _journal_page_last 22590 _journal_paper_doi 10.1039/D1NJ04526A _journal_volume 45 _journal_year 2021 _chemical_absolute_configuration ad _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C18 H28 N, Cl' _chemical_formula_sum 'C18 H28 Cl N' _chemical_formula_weight 293.86 _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 geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_update_record ; 2021-09-16 deposited with the CCDC. 2021-11-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 118.618(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.0788(17) _cell_length_b 7.5785(11) _cell_length_c 11.6867(18) _cell_measurement_reflns_used 1763 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 22.76 _cell_measurement_theta_min 3.34 _cell_measurement_wavelength 0.71073 _cell_volume 861.3(2) _computing_cell_refinement 'Bruker APEX2 (Bruker, 2014)' _computing_data_collection 'Bruker APEX2 (Bruker, 2014)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2014)' _computing_molecular_graphics ; 'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)' ; _computing_publication_material 'CRYSCALC (T. Roisnel, local program, 2020)' _computing_structure_refinement 'SHELXL-2018_3 (Sheldrick, 2018)' _computing_structure_solution 'SIR97 (A. Altomare et al., 1999)' _diffrn_ambient_temperature 150(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.970 _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_orient_matrix_UB_11 0.0274617 _diffrn_orient_matrix_UB_12 0.1115226 _diffrn_orient_matrix_UB_13 0.0520858 _diffrn_orient_matrix_UB_21 -0.0434003 _diffrn_orient_matrix_UB_22 -0.0434537 _diffrn_orient_matrix_UB_23 0.0525669 _diffrn_orient_matrix_UB_31 0.0890788 _diffrn_orient_matrix_UB_32 -0.0555520 _diffrn_orient_matrix_UB_33 0.0634453 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0636 _diffrn_reflns_av_unetI/netI 0.0966 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 6699 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 27.374 _diffrn_reflns_theta_min 3.342 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_correction_T_min 0.592 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.133 _exptl_crystal_description stick _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.480 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.737 _refine_diff_density_min -0.546 _refine_diff_density_rms 0.089 _refine_ls_abs_structure_details ; Flack x determined using 757 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.13(8) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 3503 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.070 _refine_ls_R_factor_all 0.1232 _refine_ls_R_factor_gt 0.0835 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1133P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1915 _refine_ls_wR_factor_ref 0.2176 _reflns_Friedel_coverage 0.726 _reflns_Friedel_fraction_full 0.862 _reflns_Friedel_fraction_max 0.823 _reflns_number_gt 2299 _reflns_number_total 3503 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d1nj04526a2.cif _cod_data_source_block DG266c _cod_depositor_comments 'Adding full bibliography for 7061069--7061073.cif.' _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7061070 _shelx_res_file ; TITL import in P 21 job.res created by SHELXL-2018/3 at 16:37:08 on 30-Aug-2021 CELL 0.71073 11.0788 7.5785 11.6867 90.000 118.618 90.000 ZERR 2.00 0.0017 0.0011 0.0018 0.000 0.005 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H N CL UNIT 36 56 2 2 MERG 2 EQIV $1 -x+1, y+1/2, -z HTAB N11 Cl1_$1 HTAB N11 Cl1 FMAP 2 PLAN 20 ACTA 50.00 BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.113300 FVAR 1.24508 MOLE 1 C1 1 0.027025 0.586537 -0.327724 11.00000 0.06297 0.03468 = 0.05436 0.00165 0.01992 0.00123 C2 1 -0.101138 0.582273 -0.458750 11.00000 0.08441 0.05331 = 0.06595 0.00337 0.02517 -0.00206 AFIX 137 H2A 2 -0.112394 0.464245 -0.496816 11.00000 -1.50000 H2B 2 -0.092934 0.669187 -0.516739 11.00000 -1.50000 H2C 2 -0.181283 0.610619 -0.447750 11.00000 -1.50000 AFIX 0 C3 1 0.151625 0.567077 -0.347732 11.00000 0.08457 0.05976 = 0.07399 0.00211 0.03928 0.00634 AFIX 137 H3A 2 0.233822 0.549760 -0.263220 11.00000 -1.50000 H3B 2 0.162556 0.673902 -0.389140 11.00000 -1.50000 H3C 2 0.139167 0.464971 -0.403788 11.00000 -1.50000 AFIX 0 C4 1 0.026904 0.743350 -0.241844 11.00000 0.04947 0.02179 = 0.07173 0.00505 0.01830 0.00402 AFIX 13 H4 2 -0.021246 0.851333 -0.292218 11.00000 -1.20000 AFIX 0 C5 1 0.166074 0.779225 -0.123985 11.00000 0.05293 0.01608 = 0.07258 -0.00270 0.02642 -0.00296 AFIX 13 H5 2 0.234012 0.807471 -0.154701 11.00000 -1.20000 AFIX 0 C6 1 0.153487 0.937529 -0.050094 11.00000 0.06470 0.02383 = 0.10397 -0.01929 0.01803 0.00395 AFIX 137 H6A 2 0.126100 1.041591 -0.106786 11.00000 -1.50000 H6B 2 0.242306 0.959769 0.027124 11.00000 -1.50000 H6C 2 0.083957 0.913085 -0.023075 11.00000 -1.50000 AFIX 0 C7 1 0.215858 0.611543 -0.035472 11.00000 0.05689 0.02012 = 0.05309 0.00231 0.02292 -0.00044 AFIX 13 H7 2 0.186369 0.626360 0.032546 11.00000 -1.20000 AFIX 0 C8 1 0.149970 0.437405 -0.108911 11.00000 0.05164 0.02474 = 0.06172 0.00388 0.01472 -0.00645 AFIX 23 H8A 2 0.212574 0.381009 -0.136383 11.00000 -1.20000 H8B 2 0.138235 0.355361 -0.049046 11.00000 -1.20000 AFIX 0 C9 1 0.013251 0.468624 -0.226332 11.00000 0.06567 0.02307 = 0.06712 -0.00261 0.02120 -0.01242 AFIX 13 H9 2 -0.044285 0.360487 -0.263036 11.00000 -1.20000 AFIX 0 C10 1 -0.061609 0.626075 -0.201420 11.00000 0.05475 0.03548 = 0.06993 0.00303 0.03031 -0.00347 AFIX 23 H10A 2 -0.161748 0.631566 -0.261691 11.00000 -1.20000 H10B 2 -0.040627 0.639922 -0.109488 11.00000 -1.20000 AFIX 0 N11 3 0.368693 0.593187 0.034897 11.00000 0.05000 0.02218 = 0.04651 0.00084 0.02375 -0.00079 AFIX 23 H11A 2 0.399964 0.616133 -0.022769 11.00000 -1.20000 H11B 2 0.389123 0.478545 0.059901 11.00000 -1.20000 AFIX 0 C12 1 0.447668 0.706852 0.152605 11.00000 0.05617 0.02108 = 0.04652 -0.00127 0.02031 -0.00769 AFIX 13 H12 2 0.439549 0.832290 0.123239 11.00000 -1.20000 AFIX 0 C13 1 0.600800 0.652149 0.214988 11.00000 0.05457 0.03963 = 0.05403 0.00013 0.02430 -0.00575 AFIX 137 H13A 2 0.655782 0.729317 0.289291 11.00000 -1.50000 H13B 2 0.632716 0.662932 0.150249 11.00000 -1.50000 H13C 2 0.610836 0.529570 0.244913 11.00000 -1.50000 AFIX 66 C14 1 0.397606 0.695048 0.250168 11.00000 0.04508 0.03387 = 0.04510 -0.00398 0.01274 -0.00615 C15 1 0.407176 0.846289 0.321327 11.00000 0.06515 0.04292 = 0.06178 -0.00838 0.02374 0.00172 AFIX 43 H15 2 0.436002 0.954405 0.300994 11.00000 -1.20000 AFIX 65 C16 1 0.374569 0.839340 0.422236 11.00000 0.06921 0.06823 = 0.07337 -0.01623 0.03478 0.00411 AFIX 43 H16 2 0.381110 0.942707 0.470869 11.00000 -1.20000 AFIX 65 C17 1 0.332392 0.681150 0.451986 11.00000 0.06576 0.10610 = 0.06451 0.00282 0.03906 0.01082 AFIX 43 H17 2 0.310106 0.676401 0.520953 11.00000 -1.20000 AFIX 65 C18 1 0.322821 0.529907 0.380829 11.00000 0.07379 0.07293 = 0.07893 0.01535 0.04247 0.00077 AFIX 43 H18 2 0.293995 0.421792 0.401163 11.00000 -1.20000 AFIX 65 C19 1 0.355428 0.536854 0.279920 11.00000 0.06031 0.04313 = 0.05766 0.00402 0.02956 -0.00366 AFIX 43 H19 2 0.348887 0.433486 0.231287 11.00000 -1.20000 AFIX 0 MOLE 2 CL1 4 0.482102 0.201320 0.124804 11.00000 0.06212 0.02289 = 0.06354 0.00281 0.03311 0.00401 HKLF 4 REM import in P 21 REM wR2 = 0.2176, GooF = S = 1.070, Restrained GooF = 1.070 for all data REM R1 = 0.0835 for 2299 Fo > 4sig(Fo) and 0.1232 for all 3503 data REM 173 parameters refined using 1 restraints END WGHT 0.1170 0.0000 REM Highest difference peak 0.737, deepest hole -0.546, 1-sigma level 0.089 Q1 1 0.4356 0.1992 0.0215 11.00000 0.05 0.74 Q2 1 0.5355 0.2038 0.0804 11.00000 0.05 0.68 Q3 1 0.4480 0.2042 0.1825 11.00000 0.05 0.58 Q4 1 0.3760 0.1993 0.0669 11.00000 0.05 0.52 Q5 1 0.5809 0.2082 0.2021 11.00000 0.05 0.51 Q6 1 0.5200 0.6918 0.1061 11.00000 0.05 0.43 Q7 1 0.3016 0.6075 0.0761 11.00000 0.05 0.38 Q8 1 0.4536 0.7057 0.2244 11.00000 0.05 0.37 Q9 1 0.3842 0.5565 0.3550 11.00000 0.05 0.33 Q10 1 0.3774 0.8339 0.3558 11.00000 0.05 0.32 Q11 1 0.3015 0.5982 -0.0734 11.00000 0.05 0.30 Q12 1 0.0371 0.5877 -0.4106 11.00000 0.05 0.29 Q13 1 0.3510 0.7052 0.1594 11.00000 0.05 0.29 Q14 1 0.2625 0.5954 -0.3044 11.00000 0.05 0.25 Q15 1 0.0986 0.7370 -0.1309 11.00000 0.05 0.25 Q16 1 0.0955 0.4637 -0.2112 11.00000 0.05 0.24 Q17 1 0.1159 0.7196 -0.2139 11.00000 0.05 0.24 Q18 1 -0.0611 0.5870 -0.3743 11.00000 0.05 0.24 Q19 1 0.5337 0.6862 0.2550 11.00000 0.05 0.23 Q20 1 0.4748 0.8336 0.4223 11.00000 0.05 0.23 ; _shelx_res_checksum 16171 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 C1 C 0.0270(8) 0.5865(9) -0.3277(7) 0.0541(18) Uani 1 1 d . . . . . C2 C -0.1011(10) 0.5823(11) -0.4588(8) 0.072(2) Uani 1 1 d . . . . . H2A H -0.112394 0.464245 -0.496816 0.109 Uiso 1 1 calc R U . . . H2B H -0.092934 0.669187 -0.516739 0.109 Uiso 1 1 calc R U . . . H2C H -0.181283 0.610619 -0.447750 0.109 Uiso 1 1 calc R U . . . C3 C 0.1516(10) 0.5671(12) -0.3477(9) 0.072(2) Uani 1 1 d . . . . . H3A H 0.233822 0.549760 -0.263220 0.108 Uiso 1 1 calc R U . . . H3B H 0.162556 0.673902 -0.389140 0.108 Uiso 1 1 calc R U . . . H3C H 0.139167 0.464971 -0.403788 0.108 Uiso 1 1 calc R U . . . C4 C 0.0269(8) 0.7434(7) -0.2418(8) 0.0521(19) Uani 1 1 d . . . . . H4 H -0.021246 0.851333 -0.292218 0.063 Uiso 1 1 calc R U . . . C5 C 0.1661(8) 0.7792(7) -0.1240(8) 0.0487(17) Uani 1 1 d . . . . . H5 H 0.234012 0.807471 -0.154701 0.058 Uiso 1 1 calc R U . . . C6 C 0.1535(9) 0.9375(9) -0.0501(10) 0.073(3) Uani 1 1 d . . . . . H6A H 0.126100 1.041591 -0.106786 0.110 Uiso 1 1 calc R U . . . H6B H 0.242306 0.959769 0.027124 0.110 Uiso 1 1 calc R U . . . H6C H 0.083957 0.913085 -0.023075 0.110 Uiso 1 1 calc R U . . . C7 C 0.2159(8) 0.6115(7) -0.0355(7) 0.0448(16) Uani 1 1 d . . . . . H7 H 0.186369 0.626360 0.032546 0.054 Uiso 1 1 calc R U . . . C8 C 0.1500(8) 0.4374(8) -0.1089(7) 0.0512(19) Uani 1 1 d . . . . . H8A H 0.212574 0.381009 -0.136383 0.061 Uiso 1 1 calc R U . . . H8B H 0.138235 0.355361 -0.049046 0.061 Uiso 1 1 calc R U . . . C9 C 0.0133(8) 0.4686(8) -0.2263(7) 0.0563(19) Uani 1 1 d . . . . . H9 H -0.044285 0.360487 -0.263036 0.068 Uiso 1 1 calc R U . . . C10 C -0.0616(8) 0.6261(9) -0.2014(8) 0.0532(18) Uani 1 1 d . . . . . H10A H -0.161748 0.631566 -0.261691 0.064 Uiso 1 1 calc R U . . . H10B H -0.040627 0.639922 -0.109488 0.064 Uiso 1 1 calc R U . . . N11 N 0.3687(5) 0.5932(6) 0.0349(5) 0.0393(12) Uani 1 1 d . . . . . H11A H 0.399964 0.616133 -0.022769 0.047 Uiso 1 1 calc R U . . . H11B H 0.389123 0.478545 0.059901 0.047 Uiso 1 1 calc R U . . . C12 C 0.4477(6) 0.7069(9) 0.1526(5) 0.0430(14) Uani 1 1 d . . . . . H12 H 0.439549 0.832290 0.123239 0.052 Uiso 1 1 calc R U . . . C13 C 0.6008(7) 0.6521(9) 0.2150(7) 0.0501(17) Uani 1 1 d . . . . . H13A H 0.655782 0.729317 0.289291 0.075 Uiso 1 1 calc R U . . . H13B H 0.632716 0.662932 0.150249 0.075 Uiso 1 1 calc R U . . . H13C H 0.610836 0.529570 0.244913 0.075 Uiso 1 1 calc R U . . . C14 C 0.3976(5) 0.6950(6) 0.2502(4) 0.0450(14) Uani 1 1 d G . . . . C15 C 0.4072(6) 0.8463(5) 0.3213(5) 0.059(2) Uani 1 1 d G . . . . H15 H 0.436002 0.954405 0.300994 0.071 Uiso 1 1 calc R U . . . C16 C 0.3746(6) 0.8393(7) 0.4222(5) 0.070(2) Uani 1 1 d G . . . . H16 H 0.381110 0.942707 0.470869 0.084 Uiso 1 1 calc R U . . . C17 C 0.3324(6) 0.6811(9) 0.4520(5) 0.076(2) Uani 1 1 d G . . . . H17 H 0.310106 0.676401 0.520953 0.091 Uiso 1 1 calc R U . . . C18 C 0.3228(7) 0.5299(7) 0.3808(6) 0.073(3) Uani 1 1 d G . . . . H18 H 0.293995 0.421792 0.401163 0.087 Uiso 1 1 calc R U . . . C19 C 0.3554(6) 0.5369(5) 0.2799(5) 0.0532(19) Uani 1 1 d G . . . . H19 H 0.348887 0.433486 0.231287 0.064 Uiso 1 1 calc R U . . . Cl1 Cl 0.48210(16) 0.2013(2) 0.12480(15) 0.0483(5) Uani 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 C1 0.063(5) 0.035(3) 0.054(4) 0.002(3) 0.020(4) 0.001(3) C2 0.084(7) 0.053(5) 0.066(5) 0.003(4) 0.025(5) -0.002(4) C3 0.085(7) 0.060(5) 0.074(6) 0.002(4) 0.039(5) 0.006(4) C4 0.049(5) 0.022(3) 0.072(5) 0.005(3) 0.018(4) 0.004(2) C5 0.053(5) 0.016(2) 0.073(5) -0.003(3) 0.026(4) -0.003(3) C6 0.065(6) 0.024(3) 0.104(7) -0.019(4) 0.018(5) 0.004(3) C7 0.057(5) 0.020(3) 0.053(4) 0.002(3) 0.023(4) 0.000(3) C8 0.052(5) 0.025(3) 0.062(5) 0.004(3) 0.015(4) -0.006(3) C9 0.066(5) 0.023(3) 0.067(5) -0.003(3) 0.021(4) -0.012(3) C10 0.055(5) 0.035(3) 0.070(5) 0.003(3) 0.030(4) -0.003(3) N11 0.050(3) 0.022(2) 0.047(3) 0.001(2) 0.024(3) -0.001(2) C12 0.056(4) 0.021(2) 0.047(3) -0.001(3) 0.020(3) -0.008(3) C13 0.055(5) 0.040(4) 0.054(4) 0.000(3) 0.024(4) -0.006(3) C14 0.045(4) 0.034(3) 0.045(3) -0.004(3) 0.013(3) -0.006(3) C15 0.065(5) 0.043(4) 0.062(5) -0.008(3) 0.024(5) 0.002(3) C16 0.069(6) 0.068(5) 0.073(6) -0.016(5) 0.035(6) 0.004(4) C17 0.066(5) 0.106(7) 0.065(5) 0.003(6) 0.039(5) 0.011(6) C18 0.074(7) 0.073(6) 0.079(6) 0.015(5) 0.042(6) 0.001(5) C19 0.060(5) 0.043(4) 0.058(5) 0.004(3) 0.030(4) -0.004(3) Cl1 0.0621(11) 0.0229(6) 0.0635(10) 0.0028(8) 0.0331(9) 0.0040(7) 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' 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 C3 C1 C2 109.0(7) . . ? C3 C1 C9 119.6(7) . . ? C2 C1 C9 112.0(7) . . ? C3 C1 C4 117.2(6) . . ? C2 C1 C4 112.3(6) . . ? C9 C1 C4 85.2(5) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C10 109.9(6) . . ? C5 C4 C1 114.0(6) . . ? C10 C4 C1 87.4(5) . . ? C5 C4 H4 114.2 . . ? C10 C4 H4 114.2 . . ? C1 C4 H4 114.2 . . ? C6 C5 C4 109.0(6) . . ? C6 C5 C7 111.4(6) . . ? C4 C5 C7 109.7(5) . . ? C6 C5 H5 108.9 . . ? C4 C5 H5 108.9 . . ? C7 C5 H5 108.9 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N11 C7 C8 109.5(5) . . ? N11 C7 C5 112.8(5) . . ? C8 C7 C5 113.7(5) . . ? N11 C7 H7 106.8 . . ? C8 C7 H7 106.8 . . ? C5 C7 H7 106.8 . . ? C9 C8 C7 111.9(5) . . ? C9 C8 H8A 109.2 . . ? C7 C8 H8A 109.2 . . ? C9 C8 H8B 109.2 . . ? C7 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C1 111.4(6) . . ? C8 C9 C10 110.2(6) . . ? C1 C9 C10 87.6(5) . . ? C8 C9 H9 114.9 . . ? C1 C9 H9 114.9 . . ? C10 C9 H9 114.9 . . ? C4 C10 C9 84.9(5) . . ? C4 C10 H10A 114.5 . . ? C9 C10 H10A 114.5 . . ? C4 C10 H10B 114.5 . . ? C9 C10 H10B 114.5 . . ? H10A C10 H10B 111.6 . . ? C7 N11 C12 117.5(5) . . ? C7 N11 H11A 107.9 . . ? C12 N11 H11A 107.9 . . ? C7 N11 H11B 107.9 . . ? C12 N11 H11B 107.9 . . ? H11A N11 H11B 107.2 . . ? C14 C12 N11 113.6(5) . . ? C14 C12 C13 110.4(5) . . ? N11 C12 C13 107.7(5) . . ? C14 C12 H12 108.3 . . ? N11 C12 H12 108.3 . . ? C13 C12 H12 108.3 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 120.0 . . ? C15 C14 C12 117.3(4) . . ? C19 C14 C12 122.4(4) . . ? C14 C15 C16 120.0 . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C17 120.0 . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C18 C17 C16 120.0 . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 120.0 . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C18 C19 C14 120.0 . . ? C18 C19 H19 120.0 . . ? C14 C19 H19 120.0 . . ? 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 C1 C3 1.514(12) . ? C1 C2 1.510(12) . ? C1 C9 1.549(10) . ? C1 C4 1.556(9) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.521(11) . ? C4 C10 1.555(10) . ? C4 H4 1.0000 . ? C5 C6 1.523(9) . ? C5 C7 1.563(8) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 N11 1.493(9) . ? C7 C8 1.553(9) . ? C7 H7 1.0000 . ? C8 C9 1.497(11) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.558(10) . ? C9 H9 1.0000 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? N11 C12 1.499(8) . ? N11 H11A 0.9100 . ? N11 H11B 0.9100 . ? C12 C14 1.490(6) . ? C12 C13 1.548(10) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.3900 . ? C14 C19 1.3900 . ? C15 C16 1.3900 . ? C15 H15 0.9500 . ? C16 C17 1.3900 . ? C16 H16 0.9500 . ? C17 C18 1.3900 . ? C17 H17 0.9500 . ? C18 C19 1.3900 . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? 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 N11 H11A Cl1 0.91 2.24 3.137(5) 166.7 2_655 yes N11 H11A Cl1 0.91 2.24 3.137(5) 166.7 2_655 yes N11 H11B Cl1 0.91 2.30 3.200(5) 168.6 . yes N11 H11B Cl1 0.91 2.30 3.200(5) 168.6 . 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 C3 C1 C4 C5 -38.9(9) . . . . ? C2 C1 C4 C5 -166.2(6) . . . . ? C9 C1 C4 C5 82.0(6) . . . . ? C3 C1 C4 C10 -149.6(7) . . . . ? C2 C1 C4 C10 83.1(7) . . . . ? C9 C1 C4 C10 -28.7(5) . . . . ? C10 C4 C5 C6 -85.1(7) . . . . ? C1 C4 C5 C6 178.6(6) . . . . ? C10 C4 C5 C7 37.0(7) . . . . ? C1 C4 C5 C7 -59.2(7) . . . . ? C6 C5 C7 N11 -90.5(7) . . . . ? C4 C5 C7 N11 148.7(5) . . . . ? C6 C5 C7 C8 144.0(7) . . . . ? C4 C5 C7 C8 23.2(8) . . . . ? N11 C7 C8 C9 -152.8(6) . . . . ? C5 C7 C8 C9 -25.5(9) . . . . ? C7 C8 C9 C1 62.7(8) . . . . ? C7 C8 C9 C10 -32.8(8) . . . . ? C3 C1 C9 C8 36.5(9) . . . . ? C2 C1 C9 C8 165.7(6) . . . . ? C4 C1 C9 C8 -82.1(6) . . . . ? C3 C1 C9 C10 147.2(7) . . . . ? C2 C1 C9 C10 -83.5(7) . . . . ? C4 C1 C9 C10 28.6(5) . . . . ? C5 C4 C10 C9 -86.1(6) . . . . ? C1 C4 C10 C9 28.5(5) . . . . ? C8 C9 C10 C4 83.3(6) . . . . ? C1 C9 C10 C4 -28.6(5) . . . . ? C8 C7 N11 C12 -154.5(5) . . . . ? C5 C7 N11 C12 77.8(6) . . . . ? C7 N11 C12 C14 52.3(7) . . . . ? C7 N11 C12 C13 175.0(5) . . . . ? N11 C12 C14 C15 -147.0(4) . . . . ? C13 C12 C14 C15 91.8(5) . . . . ? N11 C12 C14 C19 39.3(6) . . . . ? C13 C12 C14 C19 -81.9(5) . . . . ? C19 C14 C15 C16 0.0 . . . . ? C12 C14 C15 C16 -173.9(5) . . . . ? C14 C15 C16 C17 0.0 . . . . ? C15 C16 C17 C18 0.0 . . . . ? C16 C17 C18 C19 0.0 . . . . ? C17 C18 C19 C14 0.0 . . . . ? C15 C14 C19 C18 0.0 . . . . ? C12 C14 C19 C18 173.5(5) . . . . ?