#------------------------------------------------------------------------------ #$Date: 2025-02-01 03:46:00 +0200 (Sat, 01 Feb 2025) $ #$Revision: 297558 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573824.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_1573824 _journal_paper_doi 10.1039/D4OB02101K _chemical_formula_moiety 'C46 H36 N2' _chemical_formula_sum 'C46 H36 N2' _chemical_formula_weight 616.77 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2024-10-30 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2024-10-31 deposited with the CCDC. 2025-01-31 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 109.461(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 16.6526(4) _cell_length_b 5.85340(10) _cell_length_c 18.1057(5) _cell_measurement_reflns_used 4074 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 70.1840 _cell_measurement_theta_min 4.3970 _cell_volume 1664.01(7) _computing_cell_refinement 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.2312 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -108.00 -36.00 0.60 2.00 -- -33.50 178.00 -30.00 120 2 \w -92.00 -50.00 0.60 2.00 -- -33.50 178.00-120.00 70 3 \w -98.00 -15.80 0.60 2.00 -- -33.50 -57.00 60.00 137 4 \w -65.00 -20.60 0.60 2.00 -- -33.50 -57.00 -30.00 74 5 \w -46.00 -7.60 0.60 2.00 -- -33.50 19.00 120.00 64 6 \w 37.00 63.40 0.60 2.00 -- 36.47 19.00 -30.00 44 7 \w 2.00 66.80 0.60 2.00 -- 36.47 -99.00-180.00 108 8 \w 61.00 86.20 0.60 2.00 -- 36.47 178.00 -90.00 42 9 \w 61.00 103.60 0.60 2.00 -- 36.47 178.00-120.00 71 10 \w 19.00 70.60 0.60 2.00 -- 36.47 57.00 -60.00 86 11 \w 18.00 77.40 0.60 2.00 -- 36.47 57.00 -30.00 99 12 \w -17.00 49.00 0.60 2.00 -- 36.47 -77.00 -90.00 110 13 \w -18.00 30.00 0.60 2.00 -- 36.47 -77.00-120.00 80 14 \w 66.00 107.40 0.60 2.00 -- 36.47 178.00 90.00 69 15 \w 3.00 32.40 0.60 2.00 -- 36.47 19.00 -30.00 49 16 \w 38.00 74.60 0.60 2.00 -- 36.47 -99.00 -90.00 61 17 \w 26.00 52.40 0.60 2.00 -- 36.47 -99.00-150.00 44 18 \w 44.80 109.00 0.60 14.00 -- 108.00-111.00-180.00 107 19 \w 39.00 72.60 0.60 14.00 -- 108.00 -94.00-150.00 56 20 \w 119.00 167.60 0.60 14.00 -- 108.00 77.00 -60.00 81 21 \w 43.00 178.00 0.60 14.00 -- 108.00 0.00 -60.00 225 22 \w 107.00 136.40 0.60 14.00 -- 108.00 111.00 90.00 49 23 \w 66.00 101.40 0.60 14.00 -- 108.00 -95.00 75.00 59 24 \w 47.00 101.00 0.60 14.00 -- 108.00 -94.00-120.00 90 25 \w 134.00 173.60 0.60 14.00 -- 108.00 61.00 0.00 66 26 \w 82.00 176.20 0.60 14.00 -- 108.00 30.00 150.00 157 27 \w 48.00 90.60 0.60 14.00 -- 108.00 -94.00 30.00 71 28 \w 76.60 109.00 0.60 14.00 -- 108.00-111.00 -30.00 54 29 \w 115.00 163.00 0.60 14.00 -- 108.00 111.00-120.00 80 30 \w 106.00 132.40 0.60 14.00 -- 108.00 111.00-150.00 44 31 \w 95.00 169.40 0.60 14.00 -- 108.00 61.00 -30.00 124 32 \w 41.00 118.40 0.60 14.00 -- 108.00 -45.00 -30.00 129 33 \w 141.00 176.40 0.60 14.00 -- 108.00 77.00 120.00 59 34 \w 147.00 173.40 0.60 14.00 -- 108.00 61.00 -90.00 44 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0447132000 _diffrn_orient_matrix_UB_12 -0.1661743000 _diffrn_orient_matrix_UB_13 0.0396872000 _diffrn_orient_matrix_UB_21 -0.0680404000 _diffrn_orient_matrix_UB_22 0.1825785000 _diffrn_orient_matrix_UB_23 -0.0043417000 _diffrn_orient_matrix_UB_31 -0.0547159000 _diffrn_orient_matrix_UB_32 -0.0911769000 _diffrn_orient_matrix_UB_33 -0.0809616000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_unetI/netI 0.0275 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 10833 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.069 _diffrn_reflns_theta_max 67.069 _diffrn_reflns_theta_min 4.416 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.541 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92653 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.231 _exptl_crystal_description block _exptl_crystal_F_000 652 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.335 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 224 _refine_ls_number_reflns 2950 _refine_ls_number_restraints 60 _refine_ls_restrained_S_all 1.105 _refine_ls_R_factor_all 0.0691 _refine_ls_R_factor_gt 0.0606 _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^)+(0.1115P)^2^+0.4206P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1793 _refine_ls_wR_factor_ref 0.1901 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2455 _reflns_number_total 2950 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob02101k2.cif _cod_data_source_block t4461 _cod_database_code 1573824 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula C12H22O5N1 _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_max 0.958 _shelx_estimated_absorpt_t_min 0.918 _reflns_odcompleteness_completeness 99.88 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Uiso/Uaniso restraints and constraints Uanis(C22A) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C21A) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C20A) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C19A) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C23A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(C19) = Uanis(C19A) Uanis(C20) = Uanis(C20A) Uanis(C23) = Uanis(C23A) Uanis(C22) = Uanis(C22A) Uanis(C21) = Uanis(C21A) Uanis(C18) = Uanis(C18A) 3. Others Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)= Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=1-FVAR(1) Sof(C23)=Sof(H23)=Sof(C22)=Sof(H22)=Sof(C21)=Sof(H21)=Sof(C20)=Sof(H20)= Sof(C19)=Sof(H19)=Sof(C18)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C11(H11A,H11B) 4.b Aromatic/amide H refined with riding coordinates: C1(H1), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A), C23(H23), C22(H22), C21(H21), C20(H20), C19(H19), C23A(H23A) 4.c Fitted hexagon refined as free rotating group: C23(C22,C21,C20,C19,C18) ; _shelx_res_file ; t4461.res created by SHELXL-2014/7 TITL T4461 in P21/n #14 REM reset to P21/n #14 CELL 1.54184 16.6526 5.8534 18.1057 90 109.461 90 ZERR 2 0.0004 0.0001 0.0005 0 0.003 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N UNIT 92 72 4 ISOR 0.01 0.02 C22A C22 C21A C21 C20A C20 C19 C19A C23 C23A EADP C19 C19A EADP C20 C20A EADP C23 C23A EADP C22 C22A EADP C21 C21A EADP C18 C18A L.S. 4 0 0 PLAN 20 SIZE 0.08 0.11 0.16 MPLA C1 C2 C3 C4 N1 MPLA C10 C9 C8 C7 C6 C5 MPLA C18 C19 C20 C21 C22 C23 MPLA C12 C13 C14 C15 C16 C17 BOND $h conf fmap 2 acta SHEL 999 0.837 REM REM REM WGHT 0.111500 0.420600 FVAR 0.57835 0.58754 N1 3 0.390298 0.882027 0.418968 11.00000 0.04950 0.05012 = 0.04457 0.00759 0.01838 0.00822 C1 1 0.375179 0.873169 0.488027 11.00000 0.05246 0.04873 = 0.04716 0.00142 0.02164 0.00957 AFIX 43 H1 2 0.339085 0.970466 0.502836 11.00000 -1.20000 AFIX 0 C2 1 0.421558 0.697917 0.532643 11.00000 0.04488 0.04389 = 0.04170 -0.00031 0.01618 0.00201 C3 1 0.469397 0.595490 0.488403 11.00000 0.03934 0.04332 = 0.03954 -0.00200 0.01343 -0.00094 C4 1 0.447905 0.715623 0.419258 11.00000 0.04361 0.05017 = 0.04262 0.00137 0.01800 0.00361 AFIX 43 H4 2 0.469355 0.687769 0.378807 11.00000 -1.20000 AFIX 0 C5 1 0.413891 0.641291 0.609930 11.00000 0.04505 0.04773 = 0.04302 0.00195 0.01767 0.00939 C6 1 0.433044 0.804942 0.668809 11.00000 0.05842 0.05213 = 0.05128 -0.00268 0.02298 -0.00240 AFIX 43 H6 2 0.455580 0.944508 0.660862 11.00000 -1.20000 AFIX 0 C7 1 0.419369 0.765128 0.739045 11.00000 0.06292 0.06133 = 0.04784 -0.01102 0.02296 -0.00298 AFIX 43 H7 2 0.432856 0.878849 0.777088 11.00000 -1.20000 AFIX 0 C8 1 0.386153 0.560543 0.754142 11.00000 0.05402 0.05983 = 0.04678 0.00418 0.02080 0.00998 C9 1 0.366903 0.397332 0.695068 11.00000 0.07487 0.04952 = 0.05880 0.00279 0.03422 0.00003 AFIX 43 H9 2 0.344201 0.257954 0.702958 11.00000 -1.20000 AFIX 0 C10 1 0.380563 0.436411 0.624926 11.00000 0.07154 0.04674 = 0.05216 -0.00548 0.02792 0.00200 AFIX 43 H10 2 0.367081 0.322609 0.586912 11.00000 -1.20000 AFIX 0 C11 1 0.359864 1.060176 0.359289 11.00000 0.05701 0.05674 = 0.05594 0.01714 0.02365 0.01046 AFIX 23 H11A 2 0.362351 1.003788 0.309720 11.00000 -1.20000 H11B 2 0.397079 1.192011 0.374178 11.00000 -1.20000 AFIX 0 C12 1 0.269542 1.132225 0.349108 11.00000 0.04974 0.04626 = 0.03875 0.00692 0.01364 0.00391 C13 1 0.253649 1.337622 0.379060 11.00000 0.06441 0.04961 = 0.06206 -0.00300 0.02030 -0.00237 AFIX 43 H13 2 0.298477 1.433468 0.405719 11.00000 -1.20000 AFIX 0 C14 1 0.169767 1.400498 0.369049 11.00000 0.09508 0.05799 = 0.09303 0.01024 0.05061 0.02276 AFIX 43 H14 2 0.158627 1.539268 0.388708 11.00000 -1.20000 AFIX 0 C15 1 0.103802 1.258073 0.330299 11.00000 0.05076 0.10118 = 0.08923 0.03101 0.02461 0.01707 AFIX 43 H15 2 0.048046 1.299350 0.324279 11.00000 -1.20000 AFIX 0 C16 1 0.119977 1.056298 0.300660 11.00000 0.05442 0.10105 = 0.06694 0.00293 0.00850 -0.01485 AFIX 43 H16 2 0.075086 0.960960 0.273756 11.00000 -1.20000 AFIX 0 C17 1 0.201789 0.992986 0.310200 11.00000 0.06770 0.06017 = 0.05180 -0.00715 0.01659 -0.00916 AFIX 43 H17 2 0.211976 0.853840 0.290155 11.00000 -1.20000 AFIX 0 PART 2 C18A 1 0.362876 0.517174 0.825285 -21.00000 0.05852 0.07378 = 0.04633 0.00432 0.02184 0.00555 C19A 1 0.359844 0.692112 0.876417 -21.00000 0.10889 0.11857 = 0.06041 -0.00481 0.04066 -0.02999 AFIX 43 H19A 2 0.368007 0.840855 0.862309 -21.00000 -1.20000 AFIX 0 C20A 1 0.345643 0.660435 0.946237 -21.00000 0.13339 0.14716 = 0.06043 -0.01296 0.04315 -0.03007 AFIX 43 H20A 2 0.347987 0.783008 0.979574 -21.00000 -1.20000 AFIX 0 C21A 1 0.327810 0.442809 0.965912 -21.00000 0.10781 0.13290 = 0.06257 0.00270 0.04694 -0.01812 AFIX 43 H21A 2 0.314177 0.418912 1.011120 -21.00000 -1.20000 AFIX 0 C22A 1 0.330224 0.267362 0.919861 -21.00000 0.07625 0.10925 = 0.07674 0.01033 0.04088 -0.01330 AFIX 43 H22A 2 0.322306 0.119613 0.935032 -21.00000 -1.20000 AFIX 66 PART 0 PART 1 C23 1 0.313623 0.382039 0.837935 21.00000 0.05846 0.09150 = 0.06103 0.00177 0.02660 -0.00793 AFIX 43 H23 2 0.278298 0.309108 0.793287 21.00000 -1.20000 AFIX 65 C22 1 0.301498 0.348888 0.909508 21.00000 0.07625 0.10925 = 0.07674 0.01033 0.04088 -0.01330 AFIX 43 H22 2 0.258059 0.253777 0.912748 21.00000 -1.20000 AFIX 65 C21 1 0.354295 0.457892 0.976240 21.00000 0.10781 0.13290 = 0.06257 0.00270 0.04694 -0.01812 AFIX 43 H21 2 0.346182 0.435712 1.024127 21.00000 -1.20000 AFIX 65 C20 1 0.419219 0.600048 0.971399 21.00000 0.13339 0.14716 = 0.06043 -0.01296 0.04315 -0.03007 AFIX 43 H20 2 0.454544 0.672979 1.016047 21.00000 -1.20000 AFIX 65 C19 1 0.431346 0.633200 0.899826 21.00000 0.10889 0.11857 = 0.06041 -0.00481 0.04066 -0.02999 AFIX 43 H19 2 0.474784 0.728312 0.896588 21.00000 -1.20000 AFIX 65 C18 1 0.378549 0.524198 0.833094 21.00000 0.05852 0.07378 = 0.04633 0.00432 0.02184 0.00555 AFIX 0 PART 0 PART 2 C23A 1 0.344480 0.303054 0.849269 -21.00000 0.05846 0.09150 = 0.06103 0.00177 0.02660 -0.00793 AFIX 43 H23A 2 0.341603 0.178426 0.816626 -21.00000 -1.20000 AFIX 0 HKLF 4 REM T4461 in P21/n #14 REM R1 = 0.0606 for 2455 Fo > 4sig(Fo) and 0.0691 for all 2950 data REM 224 parameters refined using 60 restraints END WGHT 0.1115 0.4206 REM Highest difference peak 0.335, deepest hole -0.259, 1-sigma level 0.044 Q1 1 0.3258 0.6245 0.8616 11.00000 0.05 0.33 Q2 1 0.3174 0.5769 0.9380 11.00000 0.05 0.32 Q3 1 0.3951 0.7332 0.8911 11.00000 0.05 0.32 Q4 1 0.3804 0.7007 0.9615 11.00000 0.05 0.25 Q5 1 0.4390 0.4902 0.9686 11.00000 0.05 0.22 Q6 1 0.3867 0.2719 0.8623 11.00000 0.05 0.22 Q7 1 0.3351 0.4183 0.8256 11.00000 0.05 0.22 Q8 1 0.4427 0.5199 0.8924 11.00000 0.05 0.20 Q9 1 0.5000 0.5000 0.5000 10.50000 0.05 0.19 Q10 1 0.4170 0.6639 0.5657 11.00000 0.05 0.19 Q11 1 0.3612 0.5733 0.6045 11.00000 0.05 0.18 Q12 1 0.2683 1.1902 0.3831 11.00000 0.05 0.18 Q13 1 0.1403 1.3269 0.3742 11.00000 0.05 0.17 Q14 1 0.3167 0.3310 0.9502 11.00000 0.05 0.17 Q15 1 0.2401 1.0160 0.3578 11.00000 0.05 0.16 Q16 1 0.4761 0.6864 0.5325 11.00000 0.05 0.16 Q17 1 0.3748 0.6738 0.7406 11.00000 0.05 0.16 Q18 1 0.4418 0.5923 0.5112 11.00000 0.05 0.15 Q19 1 0.3032 1.1137 0.3498 11.00000 0.05 0.15 Q20 1 0.3381 0.5018 0.7137 11.00000 0.05 0.15 ; _shelx_res_checksum 50736 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.870 _oxdiff_exptl_absorpt_empirical_full_min 0.864 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 N1 N 0.39030(10) 0.8820(3) 0.41897(10) 0.0474(4) Uani 1 1 d . . . . . C1 C 0.37518(13) 0.8732(3) 0.48803(12) 0.0482(5) Uani 1 1 d . . . . . H1 H 0.3391 0.9705 0.5028 0.058 Uiso 1 1 calc R . . . . C2 C 0.42156(12) 0.6979(3) 0.53264(11) 0.0430(4) Uani 1 1 d . . . . . C3 C 0.46940(11) 0.5955(3) 0.48840(10) 0.0407(4) Uani 1 1 d . . . . . C4 C 0.44791(12) 0.7156(3) 0.41926(11) 0.0446(5) Uani 1 1 d . . . . . H4 H 0.4694 0.6878 0.3788 0.053 Uiso 1 1 calc R . . . . C5 C 0.41389(12) 0.6413(3) 0.60993(11) 0.0445(5) Uani 1 1 d . . . . . C6 C 0.43304(14) 0.8049(4) 0.66881(12) 0.0528(5) Uani 1 1 d . . . . . H6 H 0.4556 0.9445 0.6609 0.063 Uiso 1 1 calc R . . . . C7 C 0.41937(14) 0.7651(4) 0.73904(12) 0.0562(5) Uani 1 1 d . . . . . H7 H 0.4329 0.8788 0.7771 0.067 Uiso 1 1 calc R . . . . C8 C 0.38615(13) 0.5605(4) 0.75414(12) 0.0525(5) Uani 1 1 d . . . . . C9 C 0.36690(16) 0.3973(4) 0.69507(13) 0.0581(6) Uani 1 1 d . . . . . H9 H 0.3442 0.2580 0.7030 0.070 Uiso 1 1 calc R . . . . C10 C 0.38056(15) 0.4364(4) 0.62493(13) 0.0550(5) Uani 1 1 d . . . . . H10 H 0.3671 0.3226 0.5869 0.066 Uiso 1 1 calc R . . . . C11 C 0.35986(14) 1.0602(4) 0.35929(13) 0.0554(5) Uani 1 1 d . . . . . H11A H 0.3624 1.0038 0.3097 0.066 Uiso 1 1 calc R . . . . H11B H 0.3971 1.1920 0.3742 0.066 Uiso 1 1 calc R . . . . C12 C 0.26954(12) 1.1322(3) 0.34911(11) 0.0452(5) Uani 1 1 d . . . . . C13 C 0.25365(15) 1.3376(4) 0.37906(14) 0.0589(6) Uani 1 1 d . . . . . H13 H 0.2985 1.4335 0.4057 0.071 Uiso 1 1 calc R . . . . C14 C 0.1698(2) 1.4005(5) 0.36905(18) 0.0772(8) Uani 1 1 d . . . . . H14 H 0.1586 1.5393 0.3887 0.093 Uiso 1 1 calc R . . . . C15 C 0.10380(16) 1.2581(6) 0.33030(18) 0.0801(9) Uani 1 1 d . . . . . H15 H 0.0480 1.2993 0.3243 0.096 Uiso 1 1 calc R . . . . C16 C 0.11998(16) 1.0563(6) 0.30066(16) 0.0771(8) Uani 1 1 d . . . . . H16 H 0.0751 0.9610 0.2738 0.092 Uiso 1 1 calc R . . . . C17 C 0.20179(15) 0.9930(4) 0.31020(13) 0.0607(6) Uani 1 1 d . . . . . H17 H 0.2120 0.8538 0.2902 0.073 Uiso 1 1 calc R . . . . C18A C 0.3629(7) 0.5172(19) 0.8253(4) 0.0585(9) Uani 0.412(3) 1 d . . P A 2 C19A C 0.3598(6) 0.6921(17) 0.8764(4) 0.0928(14) Uani 0.412(3) 1 d . U P A 2 H19A H 0.3680 0.8409 0.8623 0.111 Uiso 0.412(3) 1 calc R . P A 2 C20A C 0.3456(7) 0.660(2) 0.9462(5) 0.1109(18) Uani 0.412(3) 1 d . U P A 2 H20A H 0.3480 0.7830 0.9796 0.133 Uiso 0.412(3) 1 calc R . P A 2 C21A C 0.3278(9) 0.443(2) 0.9659(6) 0.0965(19) Uani 0.412(3) 1 d . U P A 2 H21A H 0.3142 0.4189 1.0111 0.116 Uiso 0.412(3) 1 calc R . P A 2 C22A C 0.3302(6) 0.2674(19) 0.9199(6) 0.0836(17) Uani 0.412(3) 1 d . U P A 2 H22A H 0.3223 0.1196 0.9350 0.100 Uiso 0.412(3) 1 calc R . P A 2 C23 C 0.3136(3) 0.3820(9) 0.8379(2) 0.0687(13) Uani 0.588(3) 1 d . U P A 1 H23 H 0.2783 0.3091 0.7933 0.082 Uiso 0.588(3) 1 calc R . P A 1 C22 C 0.3015(3) 0.3489(9) 0.9095(3) 0.0836(17) Uani 0.588(3) 1 d G U P A 1 H22 H 0.2581 0.2538 0.9127 0.100 Uiso 0.588(3) 1 calc R . P A 1 C21 C 0.3543(3) 0.4579(11) 0.9762(2) 0.0965(19) Uani 0.588(3) 1 d G U P A 1 H21 H 0.3462 0.4357 1.0241 0.116 Uiso 0.588(3) 1 calc R . P A 1 C20 C 0.4192(3) 0.6000(9) 0.97140(19) 0.1109(18) Uani 0.588(3) 1 d G U P A 1 H20 H 0.4545 0.6730 1.0160 0.133 Uiso 0.588(3) 1 calc R . P A 1 C19 C 0.4313(3) 0.6332(9) 0.8998(2) 0.0928(14) Uani 0.588(3) 1 d G U P A 1 H19 H 0.4748 0.7283 0.8966 0.111 Uiso 0.588(3) 1 calc R . P A 1 C18 C 0.3785(3) 0.5242(10) 0.83309(19) 0.0585(9) Uani 0.588(3) 1 d G . P A 1 C23A C 0.3445(5) 0.3031(15) 0.8493(5) 0.0687(13) Uani 0.412(3) 1 d . U P A 2 H23A H 0.3416 0.1784 0.8166 0.082 Uiso 0.412(3) 1 calc R . P A 2 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 N1 0.0495(9) 0.0501(9) 0.0446(9) 0.0076(7) 0.0184(7) 0.0082(7) C1 0.0525(11) 0.0487(11) 0.0472(11) 0.0014(8) 0.0216(9) 0.0096(8) C2 0.0449(9) 0.0439(10) 0.0417(10) -0.0003(7) 0.0162(8) 0.0020(8) C3 0.0393(8) 0.0433(10) 0.0395(9) -0.0020(7) 0.0134(7) -0.0009(7) C4 0.0436(9) 0.0502(11) 0.0426(10) 0.0014(8) 0.0180(7) 0.0036(8) C5 0.0451(10) 0.0477(10) 0.0430(10) 0.0020(8) 0.0177(8) 0.0094(8) C6 0.0584(12) 0.0521(11) 0.0513(11) -0.0027(9) 0.0230(9) -0.0024(9) C7 0.0629(13) 0.0613(13) 0.0478(11) -0.0110(9) 0.0230(10) -0.0030(10) C8 0.0540(11) 0.0598(12) 0.0468(11) 0.0042(9) 0.0208(9) 0.0100(9) C9 0.0749(14) 0.0495(12) 0.0588(13) 0.0028(9) 0.0342(11) 0.0000(10) C10 0.0715(13) 0.0467(11) 0.0522(12) -0.0055(9) 0.0279(10) 0.0020(10) C11 0.0570(12) 0.0567(12) 0.0559(12) 0.0171(10) 0.0236(9) 0.0105(9) C12 0.0497(10) 0.0463(10) 0.0388(9) 0.0069(8) 0.0136(8) 0.0039(8) C13 0.0644(13) 0.0496(12) 0.0621(13) -0.0030(10) 0.0203(10) -0.0024(10) C14 0.095(2) 0.0580(15) 0.0930(19) 0.0102(13) 0.0506(16) 0.0228(14) C15 0.0508(13) 0.101(2) 0.0892(19) 0.0310(17) 0.0246(13) 0.0171(14) C16 0.0544(13) 0.101(2) 0.0669(15) 0.0029(14) 0.0085(11) -0.0149(14) C17 0.0677(14) 0.0602(13) 0.0518(12) -0.0071(10) 0.0166(10) -0.0092(11) C18A 0.059(3) 0.0738(16) 0.0463(14) 0.0043(12) 0.0218(15) 0.0056(16) C19A 0.109(3) 0.119(3) 0.060(2) -0.005(2) 0.041(2) -0.030(3) C20A 0.133(4) 0.147(4) 0.060(2) -0.013(3) 0.043(3) -0.030(4) C21A 0.108(5) 0.133(3) 0.063(2) 0.003(2) 0.047(3) -0.018(3) C22A 0.076(3) 0.109(4) 0.077(2) 0.010(3) 0.041(3) -0.013(3) C23 0.058(3) 0.092(3) 0.061(2) 0.002(2) 0.027(2) -0.008(2) C22 0.076(3) 0.109(4) 0.077(2) 0.010(3) 0.041(3) -0.013(3) C21 0.108(5) 0.133(3) 0.063(2) 0.003(2) 0.047(3) -0.018(3) C20 0.133(4) 0.147(4) 0.060(2) -0.013(3) 0.043(3) -0.030(4) C19 0.109(3) 0.119(3) 0.060(2) -0.005(2) 0.041(2) -0.030(3) C18 0.059(3) 0.0738(16) 0.0463(14) 0.0043(12) 0.0218(15) 0.0056(16) C23A 0.058(3) 0.092(3) 0.061(2) 0.002(2) 0.027(2) -0.008(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 '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 C1 N1 C4 108.36(16) . . ? C1 N1 C11 125.61(17) . . ? C4 N1 C11 125.47(17) . . ? N1 C1 H1 125.4 . . ? N1 C1 C2 109.28(17) . . ? C2 C1 H1 125.4 . . ? C1 C2 C3 106.96(17) . . ? C1 C2 C5 120.88(17) . . ? C3 C2 C5 132.13(17) . . ? C2 C3 C3 128.1(2) . 3_666 ? C4 C3 C2 105.66(16) . . ? C4 C3 C3 126.3(2) . 3_666 ? N1 C4 C3 109.73(16) . . ? N1 C4 H4 125.1 . . ? C3 C4 H4 125.1 . . ? C6 C5 C2 119.98(18) . . ? C10 C5 C2 122.94(18) . . ? C10 C5 C6 116.81(18) . . ? C5 C6 H6 119.2 . . ? C7 C6 C5 121.5(2) . . ? C7 C6 H6 119.2 . . ? C6 C7 H7 119.1 . . ? C8 C7 C6 121.7(2) . . ? C8 C7 H7 119.1 . . ? C7 C8 C9 116.60(19) . . ? C7 C8 C18A 123.8(4) . . ? C7 C8 C18 118.7(3) . . ? C9 C8 C18A 119.3(4) . . ? C9 C8 C18 124.6(3) . . ? C8 C9 H9 119.1 . . ? C10 C9 C8 121.8(2) . . ? C10 C9 H9 119.1 . . ? C5 C10 H10 119.2 . . ? C9 C10 C5 121.5(2) . . ? C9 C10 H10 119.2 . . ? N1 C11 H11A 109.2 . . ? N1 C11 H11B 109.2 . . ? N1 C11 C12 111.95(17) . . ? H11A C11 H11B 107.9 . . ? C12 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C13 C12 C11 120.5(2) . . ? C17 C12 C11 120.5(2) . . ? C17 C12 C13 118.9(2) . . ? C12 C13 H13 120.2 . . ? C12 C13 C14 119.5(2) . . ? C14 C13 H13 120.2 . . ? C13 C14 H14 119.9 . . ? C15 C14 C13 120.1(3) . . ? C15 C14 H14 119.9 . . ? C14 C15 H15 120.0 . . ? C16 C15 C14 120.0(2) . . ? C16 C15 H15 120.0 . . ? C15 C16 H16 119.8 . . ? C15 C16 C17 120.4(3) . . ? C17 C16 H16 119.8 . . ? C12 C17 H17 119.5 . . ? C16 C17 C12 121.0(2) . . ? C16 C17 H17 119.5 . . ? C19A C18A C8 121.9(8) . . ? C19A C18A C23A 113.2(6) . . ? C23A C18A C8 124.9(8) . . ? C18A C19A H19A 117.7 . . ? C20A C19A C18A 124.6(9) . . ? C20A C19A H19A 117.7 . . ? C19A C20A H20A 120.7 . . ? C19A C20A C21A 118.6(10) . . ? C21A C20A H20A 120.7 . . ? C20A C21A H21A 120.1 . . ? C22A C21A C20A 119.7(8) . . ? C22A C21A H21A 120.1 . . ? C21A C22A H22A 119.7 . . ? C21A C22A C23A 120.6(9) . . ? C23A C22A H22A 119.7 . . ? C22 C23 H23 120.0 . . ? C22 C23 C18 120.0 . . ? C18 C23 H23 120.0 . . ? C23 C22 H22 120.0 . . ? C21 C22 C23 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C21 H21 120.0 . . ? C22 C21 C20 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C20 H20 120.0 . . ? C19 C20 C21 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C19 H19 120.0 . . ? C20 C19 C18 120.0 . . ? C18 C19 H19 120.0 . . ? C23 C18 C8 117.5(3) . . ? C19 C18 C8 122.4(3) . . ? C19 C18 C23 120.0 . . ? C18A C23A H23A 118.5 . . ? C22A C23A C18A 122.9(8) . . ? C22A C23A H23A 118.5 . . ? 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 N1 C1 1.356(3) . ? N1 C4 1.366(2) . ? N1 C11 1.465(2) . ? C1 H1 0.9300 . ? C1 C2 1.373(3) . ? C2 C3 1.436(3) . ? C2 C5 1.484(3) . ? C3 C3 1.476(4) 3_666 ? C3 C4 1.375(3) . ? C4 H4 0.9300 . ? C5 C6 1.389(3) . ? C5 C10 1.386(3) . ? C6 H6 0.9300 . ? C6 C7 1.384(3) . ? C7 H7 0.9300 . ? C7 C8 1.384(3) . ? C8 C9 1.390(3) . ? C8 C18A 1.485(7) . ? C8 C18 1.492(4) . ? C9 H9 0.9300 . ? C9 C10 1.382(3) . ? C10 H10 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.513(3) . ? C12 C13 1.380(3) . ? C12 C17 1.380(3) . ? C13 H13 0.9300 . ? C13 C14 1.397(4) . ? C14 H14 0.9300 . ? C14 C15 1.371(4) . ? C15 H15 0.9300 . ? C15 C16 1.361(4) . ? C16 H16 0.9300 . ? C16 C17 1.366(4) . ? C17 H17 0.9300 . ? C18A C19A 1.393(13) . ? C18A C23A 1.394(12) . ? C19A H19A 0.9300 . ? C19A C20A 1.374(10) . ? C20A H20A 0.9300 . ? C20A C21A 1.381(16) . ? C21A H21A 0.9300 . ? C21A C22A 1.332(15) . ? C22A H22A 0.9300 . ? C22A C23A 1.391(10) . ? C23 H23 0.9300 . ? C23 C22 1.3900 . ? C23 C18 1.3900 . ? C22 H22 0.9300 . ? C22 C21 1.3900 . ? C21 H21 0.9300 . ? C21 C20 1.3900 . ? C20 H20 0.9300 . ? C20 C19 1.3900 . ? C19 H19 0.9300 . ? C19 C18 1.3900 . ? C23A H23A 0.9300 . ? 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 N1 C1 C2 C3 1.1(2) . . . . ? N1 C1 C2 C5 -176.90(17) . . . . ? N1 C11 C12 C13 104.9(2) . . . . ? N1 C11 C12 C17 -74.7(3) . . . . ? C1 N1 C4 C3 0.9(2) . . . . ? C1 N1 C11 C12 -40.1(3) . . . . ? C1 C2 C3 C3 178.3(2) . . . 3_666 ? C1 C2 C3 C4 -0.5(2) . . . . ? C1 C2 C5 C6 -59.3(3) . . . . ? C1 C2 C5 C10 114.5(2) . . . . ? C2 C3 C4 N1 -0.3(2) . . . . ? C2 C5 C6 C7 174.12(19) . . . . ? C2 C5 C10 C9 -173.9(2) . . . . ? C3 C2 C5 C6 123.3(2) . . . . ? C3 C2 C5 C10 -62.9(3) . . . . ? C3 C3 C4 N1 -179.1(2) 3_666 . . . ? C4 N1 C1 C2 -1.3(2) . . . . ? C4 N1 C11 C12 149.5(2) . . . . ? C5 C2 C3 C3 -4.0(4) . . . 3_666 ? C5 C2 C3 C4 177.2(2) . . . . ? C5 C6 C7 C8 0.1(3) . . . . ? C6 C5 C10 C9 0.1(3) . . . . ? C6 C7 C8 C9 -0.2(3) . . . . ? C6 C7 C8 C18A -174.1(6) . . . . ? C6 C7 C8 C18 176.0(3) . . . . ? C7 C8 C9 C10 0.3(3) . . . . ? C7 C8 C18A C19A 10.6(13) . . . . ? C7 C8 C18A C23A -167.5(7) . . . . ? C7 C8 C18 C23 150.8(3) . . . . ? C7 C8 C18 C19 -26.7(5) . . . . ? C8 C9 C10 C5 -0.3(4) . . . . ? C8 C18A C19A C20A -174.4(8) . . . . ? C8 C18A C23A C22A 174.2(7) . . . . ? C9 C8 C18A C19A -163.1(8) . . . . ? C9 C8 C18A C23A 18.8(13) . . . . ? C9 C8 C18 C23 -33.3(5) . . . . ? C9 C8 C18 C19 149.2(3) . . . . ? C10 C5 C6 C7 -0.1(3) . . . . ? C11 N1 C1 C2 -173.07(19) . . . . ? C11 N1 C4 C3 172.76(19) . . . . ? C11 C12 C13 C14 -179.9(2) . . . . ? C11 C12 C17 C16 180.0(2) . . . . ? C12 C13 C14 C15 0.5(4) . . . . ? C13 C12 C17 C16 0.4(3) . . . . ? C13 C14 C15 C16 -0.8(4) . . . . ? C14 C15 C16 C17 0.9(4) . . . . ? C15 C16 C17 C12 -0.7(4) . . . . ? C17 C12 C13 C14 -0.4(3) . . . . ? C18A C8 C9 C10 174.5(5) . . . . ? C18A C19A C20A C21A -4.2(18) . . . . ? C19A C18A C23A C22A -4.0(15) . . . . ? C19A C20A C21A C22A 4(2) . . . . ? C20A C21A C22A C23A -4.7(19) . . . . ? C21A C22A C23A C18A 4.7(15) . . . . ? C23 C22 C21 C20 0.0 . . . . ? C22 C23 C18 C8 -177.6(5) . . . . ? C22 C23 C18 C19 0.0 . . . . ? C22 C21 C20 C19 0.0 . . . . ? C21 C20 C19 C18 0.0 . . . . ? C20 C19 C18 C8 177.4(6) . . . . ? C20 C19 C18 C23 0.0 . . . . ? C18 C8 C9 C10 -175.7(3) . . . . ? C18 C23 C22 C21 0.0 . . . . ? C23A C18A C19A C20A 3.9(16) . . . . ?