#------------------------------------------------------------------------------ #$Date: 2025-02-01 03:46:00 +0200 (Sat, 01 Feb 2025) $ #$Revision: 297558 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573825.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_1573825 _journal_paper_doi 10.1039/D4OB02101K _chemical_formula_moiety 'C38 H32 N2 O2' _chemical_formula_sum 'C38 H32 N2 O2' _chemical_formula_weight 548.65 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2024-12-26 _audit_creation_method ; Olex2 1.5 (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _audit_update_record ; 2024-12-28 deposited with the CCDC. 2025-01-31 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 116.268(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 26.2762(11) _cell_length_b 10.1154(3) _cell_length_c 12.3299(5) _cell_measurement_reflns_used 7091 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 28.7170 _cell_measurement_theta_min 1.7520 _cell_volume 2938.8(2) _computing_cell_refinement 'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)' _computing_data_reduction 'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.00(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.878 _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 -78.00 -53.00 0.50 0.80 -- -20.24 127.00-104.00 50 2 \w -89.00 -64.00 0.50 0.80 -- -20.24 145.00 63.00 50 3 \w -42.00 62.00 0.50 0.80 -- -20.24 38.00 120.00 208 4 \w -25.00 55.00 0.50 0.80 -- -20.24 19.00 30.00 160 5 \w -21.00 17.00 0.50 0.80 -- 22.51 19.00 -30.00 76 6 \w 49.00 74.00 0.50 0.80 -- 22.51-145.00 10.00 50 7 \w 32.00 95.00 0.50 0.80 -- 22.51-127.00 179.00 126 8 \w 61.00 87.00 0.50 0.80 -- 22.51 19.00 -30.00 52 9 \w 46.00 105.00 0.50 0.80 -- 22.51 178.00 90.00 118 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0136254865 _diffrn_orient_matrix_UB_12 -0.0559456841 _diffrn_orient_matrix_UB_13 -0.0357560808 _diffrn_orient_matrix_UB_21 0.0200945938 _diffrn_orient_matrix_UB_22 -0.0420017530 _diffrn_orient_matrix_UB_23 0.0443943596 _diffrn_orient_matrix_UB_31 -0.0178120638 _diffrn_orient_matrix_UB_32 -0.0046181813 _diffrn_orient_matrix_UB_33 0.0294218329 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_unetI/netI 0.0257 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.878 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 11065 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.878 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.940 _diffrn_reflns_theta_min 1.728 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Mova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.97354 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.240 _exptl_crystal_description block _exptl_crystal_F_000 1160 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.207 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 3418 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.081 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0384 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+1.3865P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0925 _refine_ls_wR_factor_ref 0.0987 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2812 _reflns_number_total 3418 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob02101k2.cif _cod_data_source_block 202412t496f1_auto _cod_database_code 1573825 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula CHNOCl _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 0.992 _shelx_estimated_absorpt_t_min 0.989 _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 Secondary CH2 refined with riding coordinates: C13(H13A,H13B) 2.b Aromatic/amide H refined with riding coordinates: C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19) 2.c Idealised Me refined as rotating group: C1(H1A,H1B,H1C) ; _shelx_res_file ; TITL 202412t496f1_auto_a.res in C2/c 202412t496f1_auto.res created by SHELXL-2019/3 at 16:58:13 on 26-Dec-2024 REM Old TITL 202412ZY8_auto in C2/c REM SHELXT solution in C2/c: R1 0.132, Rweak 0.027, Alpha 0.019 REM 0.335 for 181 systematic absences, Orientation as input REM Formula found by SHELXT: C19 N O CELL 0.71073 26.2762 10.1154 12.3299 90 116.268 90 ZERR 4 0.0011 0.0003 0.0005 0 0.005 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N O UNIT 152 128 8 8 L.S. 4 0 0 PLAN 1 SIZE 0.1 0.12 0.15 TEMP -123 CONF MPLA C3 C4 C5 C6 N1 MPLA C7 C8 C9 C10 C11 C12 MPLA C14 C15 C16 C17 C18 C19 BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.041800 1.386500 FVAR 0.29626 O1 4 0.645881 0.729498 0.712484 11.00000 0.02352 0.05531 = 0.02164 0.00426 0.00672 0.00162 N1 3 0.611590 0.786820 0.464569 11.00000 0.01484 0.02683 = 0.01977 0.00029 0.00751 -0.00132 C1 1 0.554005 0.744239 0.700463 11.00000 0.02826 0.07181 = 0.02198 0.00245 0.01265 0.00118 AFIX 137 H1A 2 0.573705 0.717242 0.785447 11.00000 -1.50000 H1B 2 0.523324 0.681654 0.655930 11.00000 -1.50000 H1C 2 0.538087 0.832943 0.695257 11.00000 -1.50000 AFIX 0 C2 1 0.595380 0.745592 0.646254 11.00000 0.02194 0.02568 = 0.02048 -0.00165 0.00841 -0.00155 C3 1 0.574556 0.766958 0.516160 11.00000 0.01801 0.02194 = 0.02076 -0.00155 0.01002 -0.00118 C4 1 0.519372 0.769842 0.421878 11.00000 0.01874 0.02121 = 0.02013 -0.00193 0.00921 -0.00124 C5 1 0.523344 0.789824 0.311651 11.00000 0.01780 0.02489 = 0.02050 -0.00113 0.00848 -0.00055 C6 1 0.580985 0.801700 0.343708 11.00000 0.01895 0.03016 = 0.01919 0.00096 0.00906 -0.00082 AFIX 43 H6 2 0.596601 0.817921 0.288660 11.00000 -1.20000 AFIX 0 C7 1 0.465033 0.753986 0.431017 11.00000 0.01692 0.02562 = 0.01665 0.00128 0.00674 -0.00130 C8 1 0.438963 0.861888 0.455652 11.00000 0.02271 0.02652 = 0.02970 -0.00256 0.01306 -0.00270 AFIX 43 H8 2 0.456631 0.946231 0.469389 11.00000 -1.20000 AFIX 0 C9 1 0.387444 0.847673 0.460380 11.00000 0.02469 0.03877 = 0.03276 0.00089 0.01667 0.00496 AFIX 43 H9 2 0.370208 0.922049 0.477715 11.00000 -1.20000 AFIX 0 C10 1 0.361196 0.725947 0.439997 11.00000 0.02143 0.04834 = 0.03533 0.00616 0.01685 -0.00322 AFIX 43 H10 2 0.325939 0.716395 0.443284 11.00000 -1.20000 AFIX 0 C11 1 0.386353 0.617849 0.414762 11.00000 0.03180 0.03373 = 0.04282 0.00250 0.01858 -0.01123 AFIX 43 H11 2 0.368265 0.533976 0.400334 11.00000 -1.20000 AFIX 0 C12 1 0.438130 0.631675 0.410455 11.00000 0.02816 0.02552 = 0.03255 0.00079 0.01518 -0.00205 AFIX 43 H12 2 0.455252 0.556947 0.393326 11.00000 -1.20000 AFIX 0 C13 1 0.674045 0.793862 0.523746 11.00000 0.01401 0.02636 = 0.02195 -0.00109 0.00656 -0.00342 AFIX 23 H13A 2 0.686513 0.835238 0.604258 11.00000 -1.20000 H13B 2 0.686313 0.852212 0.475269 11.00000 -1.20000 AFIX 0 C14 1 0.703647 0.662048 0.539805 11.00000 0.01515 0.02511 = 0.02176 0.00111 0.00932 -0.00394 C15 1 0.746512 0.627136 0.652750 11.00000 0.02256 0.03185 = 0.02070 0.00094 0.00985 -0.00132 AFIX 43 H15 2 0.754607 0.682624 0.720592 11.00000 -1.20000 AFIX 0 C16 1 0.777483 0.511615 0.666706 11.00000 0.02547 0.03229 = 0.02794 0.00919 0.01071 0.00186 AFIX 43 H16 2 0.806741 0.488911 0.743932 11.00000 -1.20000 AFIX 0 C17 1 0.765946 0.429466 0.568746 11.00000 0.02815 0.02309 = 0.04068 0.00500 0.01838 0.00002 AFIX 43 H17 2 0.787155 0.350556 0.578609 11.00000 -1.20000 AFIX 0 C18 1 0.723186 0.463120 0.455995 11.00000 0.03014 0.02599 = 0.03354 -0.00533 0.01594 -0.00596 AFIX 43 H18 2 0.715008 0.407054 0.388478 11.00000 -1.20000 AFIX 0 C19 1 0.692387 0.578685 0.441925 11.00000 0.02061 0.02851 = 0.02305 -0.00085 0.00743 -0.00431 AFIX 43 H19 2 0.663245 0.601190 0.364500 11.00000 -1.20000 AFIX 0 HKLF 4 REM 202412t496f1_auto_a.res in C2/c REM wR2 = 0.0987, GooF = S = 1.081, Restrained GooF = 1.081 for all data REM R1 = 0.0384 for 2812 Fo > 4sig(Fo) and 0.0486 for all 3418 data REM 191 parameters refined using 0 restraints END WGHT 0.0417 1.3859 REM Highest difference peak 0.207, deepest hole -0.216, 1-sigma level 0.039 Q1 1 0.5178 0.7846 0.3627 11.00000 0.05 0.21 ; _shelx_res_checksum 58181 _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 1.279 _oxdiff_exptl_absorpt_empirical_full_min 0.786 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 O1 O 0.64588(4) 0.72950(10) 0.71248(8) 0.0347(2) Uani 1 1 d . . . . . N1 N 0.61159(4) 0.78682(9) 0.46457(8) 0.0205(2) Uani 1 1 d . . . . . C1 C 0.55401(6) 0.74424(17) 0.70046(12) 0.0401(4) Uani 1 1 d . . . . . H1A H 0.573705 0.717242 0.785447 0.060 Uiso 1 1 calc R U . . . H1B H 0.523324 0.681654 0.655930 0.060 Uiso 1 1 calc R U . . . H1C H 0.538087 0.832943 0.695257 0.060 Uiso 1 1 calc R U . . . C2 C 0.59538(5) 0.74559(11) 0.64625(10) 0.0231(2) Uani 1 1 d . . . . . C3 C 0.57456(4) 0.76696(11) 0.51616(10) 0.0197(2) Uani 1 1 d . . . . . C4 C 0.51937(5) 0.76984(11) 0.42188(10) 0.0198(2) Uani 1 1 d . . . . . C5 C 0.52334(4) 0.78982(11) 0.31165(10) 0.0211(2) Uani 1 1 d . . . . . C6 C 0.58098(5) 0.80170(12) 0.34371(10) 0.0225(2) Uani 1 1 d . . . . . H6 H 0.596601 0.817921 0.288660 0.027 Uiso 1 1 calc R U . . . C7 C 0.46503(4) 0.75399(11) 0.43102(10) 0.0200(2) Uani 1 1 d . . . . . C8 C 0.43896(5) 0.86189(12) 0.45565(11) 0.0258(3) Uani 1 1 d . . . . . H8 H 0.456631 0.946231 0.469389 0.031 Uiso 1 1 calc R U . . . C9 C 0.38744(5) 0.84767(13) 0.46038(11) 0.0306(3) Uani 1 1 d . . . . . H9 H 0.370208 0.922049 0.477715 0.037 Uiso 1 1 calc R U . . . C10 C 0.36120(5) 0.72595(14) 0.44000(12) 0.0335(3) Uani 1 1 d . . . . . H10 H 0.325939 0.716395 0.443284 0.040 Uiso 1 1 calc R U . . . C11 C 0.38635(6) 0.61785(14) 0.41476(13) 0.0354(3) Uani 1 1 d . . . . . H11 H 0.368265 0.533976 0.400334 0.042 Uiso 1 1 calc R U . . . C12 C 0.43813(5) 0.63167(12) 0.41045(11) 0.0281(3) Uani 1 1 d . . . . . H12 H 0.455252 0.556947 0.393326 0.034 Uiso 1 1 calc R U . . . C13 C 0.67405(4) 0.79386(11) 0.52375(10) 0.0213(2) Uani 1 1 d . . . . . H13A H 0.686513 0.835238 0.604258 0.026 Uiso 1 1 calc R U . . . H13B H 0.686313 0.852212 0.475269 0.026 Uiso 1 1 calc R U . . . C14 C 0.70365(4) 0.66205(11) 0.53981(10) 0.0202(2) Uani 1 1 d . . . . . C15 C 0.74651(5) 0.62714(12) 0.65275(10) 0.0249(3) Uani 1 1 d . . . . . H15 H 0.754607 0.682624 0.720592 0.030 Uiso 1 1 calc R U . . . C16 C 0.77748(5) 0.51162(13) 0.66671(11) 0.0290(3) Uani 1 1 d . . . . . H16 H 0.806741 0.488911 0.743932 0.035 Uiso 1 1 calc R U . . . C17 C 0.76595(5) 0.42947(12) 0.56875(12) 0.0295(3) Uani 1 1 d . . . . . H17 H 0.787155 0.350556 0.578609 0.035 Uiso 1 1 calc R U . . . C18 C 0.72319(5) 0.46312(12) 0.45599(12) 0.0292(3) Uani 1 1 d . . . . . H18 H 0.715008 0.407054 0.388478 0.035 Uiso 1 1 calc R U . . . C19 C 0.69239(5) 0.57868(12) 0.44193(10) 0.0249(2) Uani 1 1 d . . . . . H19 H 0.663245 0.601190 0.364500 0.030 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 O1 0.0235(4) 0.0553(6) 0.0216(4) 0.0043(4) 0.0067(4) 0.0016(4) N1 0.0148(4) 0.0268(5) 0.0198(5) 0.0003(4) 0.0075(4) -0.0013(4) C1 0.0283(7) 0.0718(11) 0.0220(6) 0.0024(6) 0.0126(5) 0.0012(6) C2 0.0219(5) 0.0257(6) 0.0205(5) -0.0016(5) 0.0084(5) -0.0015(4) C3 0.0180(5) 0.0219(5) 0.0208(5) -0.0016(4) 0.0100(4) -0.0012(4) C4 0.0187(5) 0.0212(5) 0.0201(5) -0.0019(4) 0.0092(4) -0.0012(4) C5 0.0178(5) 0.0249(6) 0.0205(6) -0.0011(4) 0.0085(5) -0.0005(4) C6 0.0189(5) 0.0302(6) 0.0192(5) 0.0010(5) 0.0091(4) -0.0008(4) C7 0.0169(5) 0.0256(6) 0.0166(5) 0.0013(4) 0.0067(4) -0.0013(4) C8 0.0227(5) 0.0265(6) 0.0297(6) -0.0026(5) 0.0131(5) -0.0027(5) C9 0.0247(6) 0.0388(7) 0.0328(6) 0.0009(6) 0.0167(5) 0.0050(5) C10 0.0214(6) 0.0483(8) 0.0353(7) 0.0062(6) 0.0168(5) -0.0032(5) C11 0.0318(7) 0.0337(7) 0.0428(8) 0.0025(6) 0.0186(6) -0.0112(5) C12 0.0282(6) 0.0255(6) 0.0325(6) 0.0008(5) 0.0152(5) -0.0021(5) C13 0.0140(5) 0.0264(6) 0.0220(5) -0.0011(5) 0.0066(4) -0.0034(4) C14 0.0151(5) 0.0251(6) 0.0218(5) 0.0011(4) 0.0093(4) -0.0039(4) C15 0.0226(5) 0.0318(6) 0.0207(5) 0.0009(5) 0.0098(4) -0.0013(5) C16 0.0255(6) 0.0323(7) 0.0279(6) 0.0092(5) 0.0107(5) 0.0019(5) C17 0.0282(6) 0.0231(6) 0.0407(7) 0.0050(5) 0.0184(5) 0.0000(5) C18 0.0301(6) 0.0260(6) 0.0335(6) -0.0053(5) 0.0159(5) -0.0060(5) C19 0.0206(5) 0.0285(6) 0.0230(6) -0.0008(5) 0.0074(4) -0.0043(5) 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 C3 N1 C13 129.13(9) . . ? C6 N1 C3 108.93(9) . . ? C6 N1 C13 121.94(9) . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? O1 C2 C1 119.02(11) . . ? O1 C2 C3 121.36(10) . . ? C3 C2 C1 119.61(10) . . ? N1 C3 C2 121.60(10) . . ? N1 C3 C4 107.09(9) . . ? C4 C3 C2 131.31(10) . . ? C3 C4 C5 108.00(9) . . ? C3 C4 C7 127.56(10) . . ? C5 C4 C7 124.43(10) . . ? C4 C5 C5 127.36(12) . 2_655 ? C6 C5 C4 105.77(9) . . ? C6 C5 C5 126.77(12) . 2_655 ? N1 C6 C5 110.19(10) . . ? N1 C6 H6 124.9 . . ? C5 C6 H6 124.9 . . ? C8 C7 C4 120.85(10) . . ? C12 C7 C4 120.57(10) . . ? C12 C7 C8 118.53(10) . . ? C7 C8 H8 119.6 . . ? C9 C8 C7 120.75(11) . . ? C9 C8 H8 119.6 . . ? C8 C9 H9 119.9 . . ? C10 C9 C8 120.22(11) . . ? C10 C9 H9 119.9 . . ? C9 C10 H10 120.1 . . ? C9 C10 C11 119.79(11) . . ? C11 C10 H10 120.1 . . ? C10 C11 H11 119.9 . . ? C10 C11 C12 120.13(12) . . ? C12 C11 H11 119.9 . . ? C7 C12 C11 120.58(11) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? N1 C13 H13A 108.6 . . ? N1 C13 H13B 108.6 . . ? N1 C13 C14 114.71(9) . . ? H13A C13 H13B 107.6 . . ? C14 C13 H13A 108.6 . . ? C14 C13 H13B 108.6 . . ? C15 C14 C13 119.70(10) . . ? C19 C14 C13 121.39(10) . . ? C19 C14 C15 118.69(11) . . ? C14 C15 H15 119.8 . . ? C16 C15 C14 120.42(11) . . ? C16 C15 H15 119.8 . . ? C15 C16 H16 119.8 . . ? C17 C16 C15 120.41(11) . . ? C17 C16 H16 119.8 . . ? C16 C17 H17 120.2 . . ? C16 C17 C18 119.60(12) . . ? C18 C17 H17 120.2 . . ? C17 C18 H18 120.0 . . ? C19 C18 C17 120.01(12) . . ? C19 C18 H18 120.0 . . ? C14 C19 H19 119.6 . . ? C18 C19 C14 120.87(11) . . ? C18 C19 H19 119.6 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.2227(14) . ? N1 C3 1.3928(13) . ? N1 C6 1.3525(14) . ? N1 C13 1.4733(13) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C1 C2 1.5073(16) . ? C2 C3 1.4636(16) . ? C3 C4 1.4010(15) . ? C4 C5 1.4228(15) . ? C4 C7 1.4898(14) . ? C5 C5 1.472(2) 2_655 ? C5 C6 1.3909(15) . ? C6 H6 0.9500 . ? C7 C8 1.3918(16) . ? C7 C12 1.3914(16) . ? C8 H8 0.9500 . ? C8 C9 1.3880(16) . ? C9 H9 0.9500 . ? C9 C10 1.3790(19) . ? C10 H10 0.9500 . ? C10 C11 1.383(2) . ? C11 H11 0.9500 . ? C11 C12 1.3919(17) . ? C12 H12 0.9500 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 C14 1.5119(16) . ? C14 C15 1.3944(15) . ? C14 C19 1.3925(16) . ? C15 H15 0.9500 . ? C15 C16 1.3905(17) . ? C16 H16 0.9500 . ? C16 C17 1.3846(18) . ? C17 H17 0.9500 . ? C17 C18 1.3887(18) . ? C18 H18 0.9500 . ? C18 C19 1.3883(17) . ? C19 H19 0.9500 . ? 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 O1 C2 C3 N1 -8.38(17) . . . . ? O1 C2 C3 C4 170.26(12) . . . . ? N1 C3 C4 C5 0.85(12) . . . . ? N1 C3 C4 C7 -179.68(10) . . . . ? N1 C13 C14 C15 -129.85(10) . . . . ? N1 C13 C14 C19 55.52(13) . . . . ? C1 C2 C3 N1 171.18(11) . . . . ? C1 C2 C3 C4 -10.18(19) . . . . ? C2 C3 C4 C5 -177.93(11) . . . . ? C2 C3 C4 C7 1.5(2) . . . . ? C3 N1 C6 C5 -1.08(13) . . . . ? C3 N1 C13 C14 87.74(13) . . . . ? C3 C4 C5 C5 175.11(6) . . . 2_655 ? C3 C4 C5 C6 -1.47(13) . . . . ? C3 C4 C7 C8 85.89(15) . . . . ? C3 C4 C7 C12 -96.60(14) . . . . ? C4 C5 C6 N1 1.57(13) . . . . ? C4 C7 C8 C9 177.97(11) . . . . ? C4 C7 C12 C11 -177.71(11) . . . . ? C5 C4 C7 C8 -94.73(14) . . . . ? C5 C4 C7 C12 82.79(15) . . . . ? C5 C5 C6 N1 -175.03(6) 2_655 . . . ? C6 N1 C3 C2 179.05(10) . . . . ? C6 N1 C3 C4 0.12(12) . . . . ? C6 N1 C13 C14 -93.11(13) . . . . ? C7 C4 C5 C5 -4.37(14) . . . 2_655 ? C7 C4 C5 C6 179.04(10) . . . . ? C7 C8 C9 C10 -0.34(19) . . . . ? C8 C7 C12 C11 -0.14(18) . . . . ? C8 C9 C10 C11 0.0(2) . . . . ? C9 C10 C11 C12 0.3(2) . . . . ? C10 C11 C12 C7 -0.2(2) . . . . ? C12 C7 C8 C9 0.41(18) . . . . ? C13 N1 C3 C2 -1.72(17) . . . . ? C13 N1 C3 C4 179.36(10) . . . . ? C13 N1 C6 C5 179.62(10) . . . . ? C13 C14 C15 C16 -174.42(10) . . . . ? C13 C14 C19 C18 174.56(10) . . . . ? C14 C15 C16 C17 -0.33(17) . . . . ? C15 C14 C19 C18 -0.13(16) . . . . ? C15 C16 C17 C18 0.08(17) . . . . ? C16 C17 C18 C19 0.15(17) . . . . ? C17 C18 C19 C14 -0.13(17) . . . . ? C19 C14 C15 C16 0.36(16) . . . . ?