#------------------------------------------------------------------------------ #$Date: 2022-01-06 23:48:02 +0200 (Thu, 06 Jan 2022) $ #$Revision: 271866 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061069.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_7061069 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 rm/ad/rmad/syn/unk/. _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C25 H30 N2 O3' _chemical_formula_sum 'C25 H30 N2 O3' _chemical_formula_weight 406.51 _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 geom _atom_sites_solution_primary dual _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 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.4497(2) _cell_length_b 15.2211(5) _cell_length_c 19.6694(6) _cell_measurement_reflns_used 4668 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 26.05 _cell_measurement_theta_min 2.47 _cell_measurement_wavelength 0.71073 _cell_volume 2230.36(12) _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 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 150(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_orient_matrix_UB_11 0.1283597 _diffrn_orient_matrix_UB_12 0.0054145 _diffrn_orient_matrix_UB_13 -0.0142730 _diffrn_orient_matrix_UB_21 -0.0218035 _diffrn_orient_matrix_UB_22 -0.0426087 _diffrn_orient_matrix_UB_23 -0.0378067 _diffrn_orient_matrix_UB_31 -0.0326675 _diffrn_orient_matrix_UB_32 0.0497135 _diffrn_orient_matrix_UB_33 -0.0308491 _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 0.0383 _diffrn_reflns_av_unetI/netI 0.0469 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 14181 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.486 _diffrn_reflns_theta_min 1.692 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_correction_T_min 0.881 _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 1.211 _exptl_crystal_description fragment _exptl_crystal_F_000 872 _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.320 _exptl_crystal_size_min 0.250 _refine_diff_density_max 0.215 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.051 _refine_ls_abs_structure_details ; Flack x determined using 1567 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.8(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.170 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 275 _refine_ls_number_reflns 4968 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.170 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0417 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+0.2401P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0888 _refine_ls_wR_factor_ref 0.1042 _reflns_Friedel_coverage 0.738 _reflns_Friedel_fraction_full 0.991 _reflns_Friedel_fraction_max 0.957 _reflns_number_gt 4331 _reflns_number_total 4968 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d1nj04526a2.cif _cod_data_source_block DG180F1 _cod_depositor_comments 'Adding full bibliography for 7061069--7061073.cif.' _cod_original_cell_volume 2230.37(12) _cod_database_code 7061069 _shelx_res_file ; TITL import in P 21 21 21 job.res created by SHELXL-2018/3 at 09:04:40 on 26-Aug-2021 CELL 0.71073 7.4497 15.2211 19.6694 90.000 90.000 90.000 ZERR 4.00 0.0002 0.0005 0.0006 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 100 120 8 12 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.040200 0.240100 FVAR 0.79013 C1 1 1.340859 0.950433 0.732756 11.00000 0.02356 0.03019 = 0.02934 -0.00303 0.00060 0.00310 AFIX 43 H1 2 1.407870 0.913980 0.762636 11.00000 -1.20000 AFIX 0 C2 1 1.403223 1.034271 0.716755 11.00000 0.02438 0.03090 = 0.03628 -0.00685 0.00103 -0.00110 AFIX 43 H2 2 1.512707 1.054532 0.735922 11.00000 -1.20000 AFIX 0 C3 1 1.307896 1.088215 0.673411 11.00000 0.03831 0.03025 = 0.03091 -0.00232 0.00983 0.00106 AFIX 43 H3 2 1.351401 1.145210 0.662641 11.00000 -1.20000 AFIX 0 C4 1 1.148724 1.058461 0.645895 11.00000 0.03771 0.03907 = 0.02850 0.00740 0.00096 0.00544 AFIX 43 H4 2 1.081980 1.095103 0.616067 11.00000 -1.20000 AFIX 0 C5 1 1.086220 0.975366 0.661681 11.00000 0.02822 0.04219 = 0.02507 -0.00003 -0.00074 -0.00144 AFIX 43 H5 2 0.976375 0.955607 0.642495 11.00000 -1.20000 AFIX 0 C6 1 1.181117 0.920150 0.705119 11.00000 0.02279 0.02931 = 0.01856 -0.00473 0.00504 0.00018 C7 1 1.103626 0.829234 0.719634 11.00000 0.02183 0.03100 = 0.02164 -0.00802 0.00203 -0.00308 AFIX 13 H7 2 1.044405 0.809276 0.676703 11.00000 -1.20000 AFIX 0 C8 1 1.240085 0.758600 0.738403 11.00000 0.02933 0.02714 = 0.04008 -0.00714 0.00375 0.00061 AFIX 137 H8A 2 1.178108 0.702492 0.745197 11.00000 -1.50000 H8B 2 1.301838 0.775386 0.780434 11.00000 -1.50000 H8C 2 1.328000 0.752531 0.701638 11.00000 -1.50000 AFIX 0 N9 3 0.959291 0.835006 0.772158 11.00000 0.02239 0.02848 = 0.01619 -0.00434 0.00031 -0.00188 C10 1 0.788845 0.810496 0.758595 11.00000 0.02424 0.01930 = 0.01850 0.00032 -0.00107 -0.00003 O11 4 0.665860 0.813701 0.800260 11.00000 0.02313 0.03316 = 0.02038 -0.00435 0.00175 -0.00245 C12 1 0.743373 0.778029 0.688067 11.00000 0.01894 0.02395 = 0.01899 0.00050 0.00087 -0.00332 C13 1 0.762484 0.689467 0.671410 11.00000 0.03342 0.02514 = 0.01933 0.00047 -0.00408 -0.00088 AFIX 43 H13 2 0.816687 0.650154 0.702807 11.00000 -1.20000 AFIX 0 C14 1 0.702362 0.658692 0.608975 11.00000 0.03830 0.02478 = 0.02726 -0.00423 -0.00339 -0.00007 AFIX 43 H14 2 0.711408 0.598196 0.597600 11.00000 -1.20000 AFIX 0 C15 1 0.629250 0.718080 0.563923 11.00000 0.02990 0.03567 = 0.01964 -0.00649 -0.00485 -0.00226 C16 1 0.610290 0.806159 0.578685 11.00000 0.03127 0.03242 = 0.02115 0.00158 -0.00553 0.00332 AFIX 43 H16 2 0.560786 0.845572 0.546267 11.00000 -1.20000 AFIX 0 C17 1 0.665102 0.835686 0.641827 11.00000 0.02740 0.02405 = 0.02393 -0.00194 -0.00021 0.00188 AFIX 43 H17 2 0.649256 0.895677 0.653726 11.00000 -1.20000 AFIX 0 N18 3 0.573857 0.686210 0.496410 11.00000 0.05366 0.04738 = 0.02702 -0.01057 -0.01425 0.00423 O19 4 0.548316 0.607469 0.489328 11.00000 0.14650 0.04777 = 0.05211 -0.01890 -0.04133 -0.00725 O20 4 0.553286 0.739708 0.451071 11.00000 0.08085 0.06370 = 0.02582 -0.00248 -0.02018 0.01083 C21 1 1.013690 0.867300 0.840137 11.00000 0.02100 0.02921 = 0.01951 -0.00498 -0.00355 -0.00078 AFIX 13 H21 2 1.147691 0.868605 0.837321 11.00000 -1.20000 AFIX 0 C22 1 0.963666 0.965095 0.855913 11.00000 0.03023 0.02251 = 0.02150 -0.00135 -0.00028 -0.00323 AFIX 13 H22 2 1.066033 1.000364 0.837564 11.00000 -1.20000 AFIX 0 C23 1 0.970628 0.979044 0.933253 11.00000 0.03004 0.02573 = 0.02236 -0.00459 -0.00099 -0.00175 AFIX 13 H23 2 0.969583 1.042110 0.947495 11.00000 -1.20000 AFIX 0 C24 1 1.130496 0.925105 0.962331 11.00000 0.03107 0.04587 = 0.02374 -0.01198 -0.00686 0.00237 AFIX 23 H24A 2 1.229568 0.915157 0.929680 11.00000 -1.20000 H24B 2 1.175900 0.946369 1.006680 11.00000 -1.20000 AFIX 0 C25 1 0.994988 0.848414 0.967398 11.00000 0.04080 0.03117 = 0.02000 0.00100 -0.00479 0.00483 AFIX 13 H25 2 1.012896 0.808492 1.007202 11.00000 -1.20000 AFIX 0 C26 1 0.845065 0.918330 0.976503 11.00000 0.03164 0.03046 = 0.01950 -0.00343 -0.00034 0.00084 C27 1 0.834129 0.951715 1.049779 11.00000 0.04360 0.04298 = 0.02236 -0.00773 0.00304 0.00005 AFIX 137 H27A 2 0.789157 0.904723 1.079273 11.00000 -1.50000 H27B 2 0.752412 1.002095 1.051919 11.00000 -1.50000 H27C 2 0.953814 0.969706 1.065068 11.00000 -1.50000 AFIX 0 C28 1 0.654426 0.896198 0.954098 11.00000 0.03340 0.03555 = 0.02870 -0.00523 0.00555 -0.00402 AFIX 137 H28A 2 0.580863 0.949565 0.954858 11.00000 -1.50000 H28B 2 0.603029 0.852597 0.985164 11.00000 -1.50000 H28C 2 0.656849 0.872205 0.907873 11.00000 -1.50000 AFIX 0 C29 1 0.977202 0.801829 0.898484 11.00000 0.03552 0.02612 = 0.02101 -0.00042 -0.00335 0.00750 AFIX 23 H29A 2 0.854763 0.777286 0.893780 11.00000 -1.20000 H29B 2 1.063959 0.752665 0.896002 11.00000 -1.20000 AFIX 0 C30 1 0.796791 1.003633 0.822089 11.00000 0.04298 0.02454 = 0.02500 0.00208 -0.00468 0.00181 AFIX 137 H30A 2 0.784767 1.065619 0.834768 11.00000 -1.50000 H30B 2 0.690341 0.971234 0.837197 11.00000 -1.50000 H30C 2 0.808179 0.998778 0.772594 11.00000 -1.50000 AFIX 0 HKLF 4 REM import in P 21 21 21 REM wR2 = 0.1042, GooF = S = 1.170, Restrained GooF = 1.170 for all data REM R1 = 0.0417 for 4331 Fo > 4sig(Fo) and 0.0519 for all 4968 data REM 275 parameters refined using 0 restraints END WGHT 0.0570 0.0596 REM Highest difference peak 0.215, deepest hole -0.202, 1-sigma level 0.051 Q1 1 0.8865 0.9492 0.9513 11.00000 0.05 0.21 Q2 1 0.9036 0.8756 0.9689 11.00000 0.05 0.19 Q3 1 0.8683 0.8577 0.9638 11.00000 0.05 0.19 Q4 1 1.2336 0.8600 1.0373 11.00000 0.05 0.18 Q5 1 0.9714 0.8262 0.9345 11.00000 0.05 0.17 Q6 1 0.9597 0.9150 0.8363 11.00000 0.05 0.16 Q7 1 0.8756 0.7782 1.0261 11.00000 0.05 0.16 Q8 1 1.1599 1.0033 0.6404 11.00000 0.05 0.16 Q9 1 0.9475 0.8399 0.8702 11.00000 0.05 0.16 Q10 1 1.3868 0.8998 0.9543 11.00000 0.05 0.15 Q11 1 0.8270 0.9427 1.0114 11.00000 0.05 0.15 Q12 1 1.2147 0.7854 0.9290 11.00000 0.05 0.15 Q13 1 1.0758 0.8750 0.9627 11.00000 0.05 0.15 Q14 1 0.8422 0.8272 0.9751 11.00000 0.05 0.15 Q15 1 0.8541 0.7170 1.0500 11.00000 0.05 0.15 Q16 1 1.1574 0.8745 0.7055 11.00000 0.05 0.15 Q17 1 0.6724 0.6249 0.4724 11.00000 0.05 0.15 Q18 1 0.7704 0.9109 0.9646 11.00000 0.05 0.15 Q19 1 0.8182 0.7343 0.9511 11.00000 0.05 0.15 Q20 1 1.0194 0.8352 0.7469 11.00000 0.05 0.14 ; _shelx_res_checksum 74259 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 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 1.3409(3) 0.95043(17) 0.73276(13) 0.0277(5) Uani 1 1 d . . . . . H1 H 1.407870 0.913980 0.762636 0.033 Uiso 1 1 calc R U . . . C2 C 1.4032(3) 1.03427(17) 0.71675(14) 0.0305(6) Uani 1 1 d . . . . . H2 H 1.512707 1.054532 0.735922 0.037 Uiso 1 1 calc R U . . . C3 C 1.3079(4) 1.08822(18) 0.67341(13) 0.0332(6) Uani 1 1 d . . . . . H3 H 1.351401 1.145210 0.662641 0.040 Uiso 1 1 calc R U . . . C4 C 1.1487(4) 1.05846(19) 0.64589(14) 0.0351(6) Uani 1 1 d . . . . . H4 H 1.081980 1.095103 0.616067 0.042 Uiso 1 1 calc R U . . . C5 C 1.0862(3) 0.97537(18) 0.66168(13) 0.0318(6) Uani 1 1 d . . . . . H5 H 0.976375 0.955607 0.642495 0.038 Uiso 1 1 calc R U . . . C6 C 1.1811(3) 0.92015(16) 0.70512(12) 0.0236(5) Uani 1 1 d . . . . . C7 C 1.1036(3) 0.82923(16) 0.71963(12) 0.0248(5) Uani 1 1 d . . . . . H7 H 1.044405 0.809276 0.676703 0.030 Uiso 1 1 calc R U . . . C8 C 1.2401(3) 0.75860(16) 0.73840(14) 0.0322(6) Uani 1 1 d . . . . . H8A H 1.178108 0.702492 0.745197 0.048 Uiso 1 1 calc R U . . . H8B H 1.301838 0.775386 0.780434 0.048 Uiso 1 1 calc R U . . . H8C H 1.328000 0.752531 0.701638 0.048 Uiso 1 1 calc R U . . . N9 N 0.9593(2) 0.83501(13) 0.77216(9) 0.0224(4) Uani 1 1 d . . . . . C10 C 0.7888(3) 0.81050(15) 0.75859(12) 0.0207(5) Uani 1 1 d . . . . . O11 O 0.6659(2) 0.81370(11) 0.80026(8) 0.0256(4) Uani 1 1 d . . . . . C12 C 0.7434(3) 0.77803(15) 0.68807(12) 0.0206(5) Uani 1 1 d . . . . . C13 C 0.7625(3) 0.68947(16) 0.67141(12) 0.0260(5) Uani 1 1 d . . . . . H13 H 0.816687 0.650154 0.702807 0.031 Uiso 1 1 calc R U . . . C14 C 0.7024(3) 0.65869(17) 0.60898(13) 0.0301(6) Uani 1 1 d . . . . . H14 H 0.711408 0.598196 0.597600 0.036 Uiso 1 1 calc R U . . . C15 C 0.6292(3) 0.71808(18) 0.56392(13) 0.0284(6) Uani 1 1 d . . . . . C16 C 0.6103(3) 0.80616(18) 0.57869(12) 0.0283(6) Uani 1 1 d . . . . . H16 H 0.560786 0.845572 0.546267 0.034 Uiso 1 1 calc R U . . . C17 C 0.6651(3) 0.83569(16) 0.64183(12) 0.0251(5) Uani 1 1 d . . . . . H17 H 0.649256 0.895677 0.653726 0.030 Uiso 1 1 calc R U . . . N18 N 0.5739(3) 0.68621(18) 0.49641(12) 0.0427(6) Uani 1 1 d . . . . . O19 O 0.5483(4) 0.60747(17) 0.48933(13) 0.0821(9) Uani 1 1 d . . . . . O20 O 0.5533(3) 0.73971(16) 0.45107(10) 0.0568(6) Uani 1 1 d . . . . . C21 C 1.0137(3) 0.86730(16) 0.84014(12) 0.0232(5) Uani 1 1 d . . . . . H21 H 1.147691 0.868605 0.837321 0.028 Uiso 1 1 calc R U . . . C22 C 0.9637(3) 0.96510(16) 0.85591(12) 0.0247(5) Uani 1 1 d . . . . . H22 H 1.066033 1.000364 0.837564 0.030 Uiso 1 1 calc R U . . . C23 C 0.9706(3) 0.97904(16) 0.93325(12) 0.0260(5) Uani 1 1 d . . . . . H23 H 0.969583 1.042110 0.947495 0.031 Uiso 1 1 calc R U . . . C24 C 1.1305(4) 0.92511(18) 0.96233(14) 0.0336(6) Uani 1 1 d . . . . . H24A H 1.229568 0.915157 0.929680 0.040 Uiso 1 1 calc R U . . . H24B H 1.175900 0.946369 1.006680 0.040 Uiso 1 1 calc R U . . . C25 C 0.9950(3) 0.84841(18) 0.96740(13) 0.0307(6) Uani 1 1 d . . . . . H25 H 1.012896 0.808492 1.007202 0.037 Uiso 1 1 calc R U . . . C26 C 0.8451(3) 0.91833(17) 0.97650(13) 0.0272(5) Uani 1 1 d . . . . . C27 C 0.8341(4) 0.9517(2) 1.04978(13) 0.0363(6) Uani 1 1 d . . . . . H27A H 0.789157 0.904723 1.079273 0.054 Uiso 1 1 calc R U . . . H27B H 0.752412 1.002095 1.051919 0.054 Uiso 1 1 calc R U . . . H27C H 0.953814 0.969706 1.065068 0.054 Uiso 1 1 calc R U . . . C28 C 0.6544(3) 0.89620(18) 0.95410(14) 0.0326(6) Uani 1 1 d . . . . . H28A H 0.580863 0.949565 0.954858 0.049 Uiso 1 1 calc R U . . . H28B H 0.603029 0.852597 0.985164 0.049 Uiso 1 1 calc R U . . . H28C H 0.656849 0.872205 0.907873 0.049 Uiso 1 1 calc R U . . . C29 C 0.9772(3) 0.80183(16) 0.89848(12) 0.0276(6) Uani 1 1 d . . . . . H29A H 0.854763 0.777286 0.893780 0.033 Uiso 1 1 calc R U . . . H29B H 1.063959 0.752665 0.896002 0.033 Uiso 1 1 calc R U . . . C30 C 0.7968(4) 1.00363(17) 0.82209(13) 0.0308(6) Uani 1 1 d . . . . . H30A H 0.784767 1.065619 0.834768 0.046 Uiso 1 1 calc R U . . . H30B H 0.690341 0.971234 0.837197 0.046 Uiso 1 1 calc R U . . . H30C H 0.808179 0.998778 0.772594 0.046 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 C1 0.0236(12) 0.0302(13) 0.0293(13) -0.0030(11) 0.0006(11) 0.0031(10) C2 0.0244(13) 0.0309(14) 0.0363(15) -0.0068(12) 0.0010(11) -0.0011(11) C3 0.0383(15) 0.0303(13) 0.0309(15) -0.0023(12) 0.0098(12) 0.0011(12) C4 0.0377(15) 0.0391(15) 0.0285(14) 0.0074(13) 0.0010(13) 0.0054(13) C5 0.0282(13) 0.0422(16) 0.0251(13) 0.0000(12) -0.0007(11) -0.0014(12) C6 0.0228(12) 0.0293(12) 0.0186(12) -0.0047(10) 0.0050(10) 0.0002(10) C7 0.0218(11) 0.0310(13) 0.0216(12) -0.0080(11) 0.0020(10) -0.0031(10) C8 0.0293(13) 0.0271(13) 0.0401(16) -0.0071(12) 0.0037(12) 0.0006(11) N9 0.0224(10) 0.0285(11) 0.0162(10) -0.0043(9) 0.0003(8) -0.0019(8) C10 0.0242(12) 0.0193(11) 0.0185(11) 0.0003(10) -0.0011(9) 0.0000(9) O11 0.0231(8) 0.0332(9) 0.0204(8) -0.0043(7) 0.0018(7) -0.0024(7) C12 0.0189(11) 0.0239(11) 0.0190(12) 0.0005(10) 0.0009(9) -0.0033(9) C13 0.0334(13) 0.0251(12) 0.0193(12) 0.0005(10) -0.0041(10) -0.0009(10) C14 0.0383(14) 0.0248(12) 0.0273(13) -0.0042(11) -0.0034(11) -0.0001(11) C15 0.0299(13) 0.0357(14) 0.0196(12) -0.0065(11) -0.0049(11) -0.0023(11) C16 0.0313(13) 0.0324(14) 0.0211(12) 0.0016(11) -0.0055(10) 0.0033(11) C17 0.0274(12) 0.0241(11) 0.0239(12) -0.0019(10) -0.0002(10) 0.0019(10) N18 0.0537(15) 0.0474(16) 0.0270(12) -0.0106(12) -0.0143(11) 0.0042(13) O19 0.147(3) 0.0478(15) 0.0521(16) -0.0189(13) -0.0413(17) -0.0072(17) O20 0.0808(16) 0.0637(15) 0.0258(11) -0.0025(11) -0.0202(11) 0.0108(13) C21 0.0210(11) 0.0292(12) 0.0195(12) -0.0050(10) -0.0035(10) -0.0008(10) C22 0.0302(13) 0.0225(12) 0.0215(12) -0.0013(10) -0.0003(10) -0.0032(10) C23 0.0300(13) 0.0257(12) 0.0224(12) -0.0046(10) -0.0010(10) -0.0018(10) C24 0.0311(14) 0.0459(16) 0.0237(13) -0.0120(12) -0.0069(11) 0.0024(12) C25 0.0408(14) 0.0312(13) 0.0200(12) 0.0010(11) -0.0048(11) 0.0048(12) C26 0.0316(13) 0.0305(13) 0.0195(12) -0.0034(11) -0.0003(11) 0.0008(11) C27 0.0436(16) 0.0430(16) 0.0224(13) -0.0077(12) 0.0030(12) 0.0001(13) C28 0.0334(14) 0.0356(14) 0.0287(14) -0.0052(12) 0.0056(11) -0.0040(12) C29 0.0355(13) 0.0261(12) 0.0210(13) -0.0004(11) -0.0033(11) 0.0075(11) C30 0.0430(16) 0.0245(12) 0.0250(13) 0.0021(11) -0.0047(12) 0.0018(11) 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' 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 C6 C1 C2 120.1(2) . . ? C6 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C3 C2 C1 120.8(2) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 119.3(3) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 121.3(2) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.4(2) . . ? C1 C6 C7 123.5(2) . . ? C5 C6 C7 118.1(2) . . ? N9 C7 C8 110.7(2) . . ? N9 C7 C6 110.38(19) . . ? C8 C7 C6 115.62(19) . . ? N9 C7 H7 106.5 . . ? C8 C7 H7 106.5 . . ? C6 C7 H7 106.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 N9 C21 121.83(19) . . ? C10 N9 C7 121.61(19) . . ? C21 N9 C7 116.55(18) . . ? O11 C10 N9 123.9(2) . . ? O11 C10 C12 117.23(19) . . ? N9 C10 C12 118.86(19) . . ? C17 C12 C13 119.9(2) . . ? C17 C12 C10 119.2(2) . . ? C13 C12 C10 120.6(2) . . ? C14 C13 C12 120.1(2) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C15 C14 C13 118.4(2) . . ? C15 C14 H14 120.8 . . ? C13 C14 H14 120.8 . . ? C14 C15 C16 122.9(2) . . ? C14 C15 N18 118.3(2) . . ? C16 C15 N18 118.8(2) . . ? C15 C16 C17 118.4(2) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? C16 C17 C12 120.4(2) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? O20 N18 O19 123.6(2) . . ? O20 N18 C15 118.4(2) . . ? O19 N18 C15 118.0(3) . . ? N9 C21 C29 114.12(19) . . ? N9 C21 C22 115.43(19) . . ? C29 C21 C22 115.11(19) . . ? N9 C21 H21 103.3 . . ? C29 C21 H21 103.3 . . ? C22 C21 H21 103.3 . . ? C30 C22 C23 113.9(2) . . ? C30 C22 C21 118.2(2) . . ? C23 C22 C21 108.6(2) . . ? C30 C22 H22 104.9 . . ? C23 C22 H22 104.9 . . ? C21 C22 H22 104.9 . . ? C22 C23 C24 108.5(2) . . ? C22 C23 C26 115.8(2) . . ? C24 C23 C26 86.91(19) . . ? C22 C23 H23 114.2 . . ? C24 C23 H23 114.2 . . ? C26 C23 H23 114.2 . . ? C25 C24 C23 85.54(19) . . ? C25 C24 H24A 114.4 . . ? C23 C24 H24A 114.4 . . ? C25 C24 H24B 114.4 . . ? C23 C24 H24B 114.4 . . ? H24A C24 H24B 111.5 . . ? C29 C25 C24 110.4(2) . . ? C29 C25 C26 110.9(2) . . ? C24 C25 C26 87.69(19) . . ? C29 C25 H25 115.0 . . ? C24 C25 H25 115.0 . . ? C26 C25 H25 115.0 . . ? C28 C26 C27 107.2(2) . . ? C28 C26 C25 119.0(2) . . ? C27 C26 C25 112.0(2) . . ? C28 C26 C23 122.0(2) . . ? C27 C26 C23 110.3(2) . . ? C25 C26 C23 84.96(19) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C25 C29 C21 110.1(2) . . ? C25 C29 H29A 109.6 . . ? C21 C29 H29A 109.6 . . ? C25 C29 H29B 109.6 . . ? C21 C29 H29B 109.6 . . ? H29A C29 H29B 108.2 . . ? C22 C30 H30A 109.5 . . ? C22 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C22 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 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 C1 C6 1.387(3) . ? C1 C2 1.394(4) . ? C1 H1 0.9500 . ? C2 C3 1.380(4) . ? C2 H2 0.9500 . ? C3 C4 1.380(4) . ? C3 H3 0.9500 . ? C4 C5 1.383(4) . ? C4 H4 0.9500 . ? C5 C6 1.391(4) . ? C5 H5 0.9500 . ? C6 C7 1.526(3) . ? C7 N9 1.494(3) . ? C7 C8 1.525(3) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? N9 C10 1.350(3) . ? N9 C21 1.481(3) . ? C10 O11 1.230(3) . ? C10 C12 1.511(3) . ? C12 C17 1.392(3) . ? C12 C13 1.395(3) . ? C13 C14 1.389(3) . ? C13 H13 0.9500 . ? C14 C15 1.378(4) . ? C14 H14 0.9500 . ? C15 C16 1.379(4) . ? C15 N18 1.473(3) . ? C16 C17 1.382(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? N18 O20 1.217(3) . ? N18 O19 1.222(3) . ? C21 C29 1.544(3) . ? C21 C22 1.566(3) . ? C21 H21 1.0000 . ? C22 C30 1.527(3) . ? C22 C23 1.537(3) . ? C22 H22 1.0000 . ? C23 C24 1.556(4) . ? C23 C26 1.566(4) . ? C23 H23 1.0000 . ? C24 C25 1.546(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C29 1.535(3) . ? C25 C26 1.553(4) . ? C25 H25 1.0000 . ? C26 C28 1.525(4) . ? C26 C27 1.530(3) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.0(4) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C2 C1 C6 C5 -0.2(4) . . . . ? C2 C1 C6 C7 179.7(2) . . . . ? C4 C5 C6 C1 0.2(4) . . . . ? C4 C5 C6 C7 -179.6(2) . . . . ? C1 C6 C7 N9 99.9(3) . . . . ? C5 C6 C7 N9 -80.2(3) . . . . ? C1 C6 C7 C8 -26.7(3) . . . . ? C5 C6 C7 C8 153.1(2) . . . . ? C8 C7 N9 C10 -111.7(2) . . . . ? C6 C7 N9 C10 119.0(2) . . . . ? C8 C7 N9 C21 67.1(3) . . . . ? C6 C7 N9 C21 -62.2(3) . . . . ? C21 N9 C10 O11 0.9(4) . . . . ? C7 N9 C10 O11 179.7(2) . . . . ? C21 N9 C10 C12 -179.9(2) . . . . ? C7 N9 C10 C12 -1.1(3) . . . . ? O11 C10 C12 C17 80.7(3) . . . . ? N9 C10 C12 C17 -98.5(3) . . . . ? O11 C10 C12 C13 -92.8(3) . . . . ? N9 C10 C12 C13 87.9(3) . . . . ? C17 C12 C13 C14 -0.5(4) . . . . ? C10 C12 C13 C14 173.1(2) . . . . ? C12 C13 C14 C15 1.9(4) . . . . ? C13 C14 C15 C16 -1.2(4) . . . . ? C13 C14 C15 N18 177.0(2) . . . . ? C14 C15 C16 C17 -0.8(4) . . . . ? N18 C15 C16 C17 -179.1(2) . . . . ? C15 C16 C17 C12 2.3(4) . . . . ? C13 C12 C17 C16 -1.7(4) . . . . ? C10 C12 C17 C16 -175.3(2) . . . . ? C14 C15 N18 O20 -161.4(3) . . . . ? C16 C15 N18 O20 16.9(4) . . . . ? C14 C15 N18 O19 19.7(4) . . . . ? C16 C15 N18 O19 -162.0(3) . . . . ? C10 N9 C21 C29 57.9(3) . . . . ? C7 N9 C21 C29 -121.0(2) . . . . ? C10 N9 C21 C22 -78.8(3) . . . . ? C7 N9 C21 C22 102.3(2) . . . . ? N9 C21 C22 C30 29.7(3) . . . . ? C29 C21 C22 C30 -106.6(2) . . . . ? N9 C21 C22 C23 161.48(19) . . . . ? C29 C21 C22 C23 25.2(3) . . . . ? C30 C22 C23 C24 171.6(2) . . . . ? C21 C22 C23 C24 37.6(3) . . . . ? C30 C22 C23 C26 75.9(3) . . . . ? C21 C22 C23 C26 -58.1(3) . . . . ? C22 C23 C24 C25 -87.7(2) . . . . ? C26 C23 C24 C25 28.55(17) . . . . ? C23 C24 C25 C29 82.6(2) . . . . ? C23 C24 C25 C26 -28.79(18) . . . . ? C29 C25 C26 C28 41.7(3) . . . . ? C24 C25 C26 C28 152.6(2) . . . . ? C29 C25 C26 C27 167.8(2) . . . . ? C24 C25 C26 C27 -81.3(2) . . . . ? C29 C25 C26 C23 -82.3(2) . . . . ? C24 C25 C26 C23 28.60(18) . . . . ? C22 C23 C26 C28 -40.7(3) . . . . ? C24 C23 C26 C28 -149.7(2) . . . . ? C22 C23 C26 C27 -167.8(2) . . . . ? C24 C23 C26 C27 83.2(2) . . . . ? C22 C23 C26 C25 80.6(2) . . . . ? C24 C23 C26 C25 -28.44(18) . . . . ? C24 C25 C29 C21 -29.1(3) . . . . ? C26 C25 C29 C21 66.4(3) . . . . ? N9 C21 C29 C25 -166.5(2) . . . . ? C22 C21 C29 C25 -29.7(3) . . . . ?