#------------------------------------------------------------------------------ #$Date: 2025-02-01 03:46:00 +0200 (Sat, 01 Feb 2025) $ #$Revision: 297558 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573822.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_1573822 _journal_paper_doi 10.1039/D4OB02101K _chemical_formula_moiety 'C36 H36 N2' _chemical_formula_sum 'C36 H36 N2' _chemical_formula_weight 496.67 _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 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 115.082(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 28.4509(12) _cell_length_b 9.1830(3) _cell_length_c 11.7236(5) _cell_measurement_reflns_used 2542 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 70.9410 _cell_measurement_theta_min 4.1280 _cell_volume 2774.1(2) _computing_cell_refinement 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)' _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 -103.00 -17.00 1.00 1.00 -- -33.50 -37.00 90.00 86 2 \w -62.00 -36.00 1.00 1.00 -- -33.50 178.00-180.00 26 3 \w -71.00 -17.00 1.00 1.00 -- -33.50 -57.00 -30.00 54 4 \w 62.00 108.00 1.00 1.00 -- 36.47 178.00 -30.00 46 5 \w 70.00 97.00 1.00 1.00 -- 36.47 178.00 0.00 27 6 \w 62.00 92.00 1.00 1.00 -- 36.47 178.00-180.00 30 7 \w 12.00 54.00 1.00 1.00 -- 36.47 -37.00 -90.00 42 8 \w -10.00 54.00 1.00 1.00 -- 36.47 -57.00 0.00 64 9 \w -30.00 0.00 1.00 1.00 -- 36.47 -37.00 -90.00 30 10 \w 61.00 97.00 1.00 1.00 -- 36.47 178.00 -60.00 36 11 \w 41.00 97.00 1.00 3.00 -- 108.00 -77.00 60.00 56 12 \w 39.00 128.00 1.00 3.00 -- 108.00 -45.00 -30.00 89 13 \w 52.00 77.00 1.00 3.00 -- 108.00-111.00 0.00 25 14 \w 103.00 170.00 1.00 3.00 -- 108.00 77.00 -30.00 67 15 \w 84.00 110.00 1.00 3.00 -- 108.00 -30.00 60.00 26 16 \w 38.00 127.00 1.00 3.00 -- 108.00 -45.00-180.00 89 17 \w 37.00 62.00 1.00 3.00 -- 108.00 -30.00 60.00 25 18 \w 101.00 138.00 1.00 3.00 -- 108.00 77.00 90.00 37 19 \w 91.00 175.00 1.00 3.00 -- 108.00 0.00-120.00 84 20 \w 44.00 70.00 1.00 3.00 -- 108.00-104.00 49.00 26 21 \w 43.00 75.00 1.00 3.00 -- 108.00 0.00-120.00 32 ; _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 0.0094588000 _diffrn_orient_matrix_UB_12 0.0718262000 _diffrn_orient_matrix_UB_13 -0.1071733000 _diffrn_orient_matrix_UB_21 -0.0569702000 _diffrn_orient_matrix_UB_22 0.0511177000 _diffrn_orient_matrix_UB_23 -0.0615796000 _diffrn_orient_matrix_UB_31 0.0156023000 _diffrn_orient_matrix_UB_32 0.1426682000 _diffrn_orient_matrix_UB_33 0.0759238000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_unetI/netI 0.0404 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 5549 _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 3.430 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.520 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90932 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023) 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 1.189 _exptl_crystal_description block _exptl_crystal_F_000 1064 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.220 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.040 _refine_ls_extinction_coef 0.0016(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 2466 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0503 _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^)+(0.0872P)^2^+0.3981P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1408 _refine_ls_wR_factor_ref 0.1536 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2022 _reflns_number_total 2466 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob02101k2.cif _cod_data_source_block ta4151 _cod_database_code 1573822 _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 0.950 _shelx_estimated_absorpt_t_min 0.908 _reflns_odcompleteness_completeness 99.89 _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 At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C4(H4A,H4B), C11(H11A,H11B) 2.b Aromatic/amide H refined with riding coordinates: C6(H6), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17) 2.c Idealised Me refined as rotating group: C18(H18A,H18B,H18C) ; _shelx_res_file ; ta4151.res created by SHELXL-2014/7 TITL TA4151 in C2/c #15 REM reset to C2/c #15 CELL 1.54184 28.450872 9.183027 11.723589 90 115.082 90 ZERR 4 0.00122 0.0003 0.000494 0 0.0053 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N UNIT 144 144 8 L.S. 4 0 0 PLAN 20 SIZE 0.1 0.12 0.19 MPLA C1 C4 N1 MPLA C1 C2 C3 C4 MPLA C5 C6 C7 C8 C9 C10 MPLA C12 C13 C14 C15 C16 C17 BOND $H CONF fmap 2 acta SHEL 999 0.837 REM REM REM WGHT 0.087200 0.398100 EXTI 0.001613 FVAR 4.54231 N1 3 0.399185 0.417979 0.520064 11.00000 0.03941 0.04565 = 0.03353 -0.00078 0.00825 0.00352 C1 1 0.433615 0.360099 0.466443 11.00000 0.04292 0.04531 = 0.03083 0.00103 0.01107 0.00205 AFIX 23 H1A 2 0.442439 0.434964 0.420469 11.00000 -1.20000 H1B 2 0.417456 0.279187 0.410227 11.00000 -1.20000 AFIX 0 C2 1 0.481172 0.310532 0.580200 11.00000 0.03698 0.04015 = 0.02980 0.00269 0.00997 -0.00383 C3 1 0.480109 0.368499 0.684068 11.00000 0.03952 0.04006 = 0.03116 0.00257 0.01234 -0.00173 C4 1 0.432301 0.460262 0.649747 11.00000 0.04352 0.04728 = 0.03512 -0.00244 0.01230 0.00197 AFIX 23 H4A 2 0.415509 0.439709 0.704750 11.00000 -1.20000 H4B 2 0.440724 0.563123 0.655013 11.00000 -1.20000 AFIX 0 C5 1 0.520511 0.217444 0.566198 11.00000 0.03879 0.03776 = 0.03313 -0.00064 0.01279 -0.00409 C6 1 0.562394 0.157690 0.669304 11.00000 0.04316 0.04551 = 0.03315 0.00042 0.01487 -0.00154 AFIX 43 H6 2 0.565435 0.176613 0.750076 11.00000 -1.20000 AFIX 0 C7 1 0.599460 0.071289 0.654946 11.00000 0.04341 0.04315 = 0.04651 0.00460 0.01710 0.00179 C8 1 0.594448 0.041855 0.534180 11.00000 0.05579 0.05330 = 0.05278 -0.00220 0.02764 0.00713 AFIX 43 H8 2 0.618967 -0.016028 0.522895 11.00000 -1.20000 AFIX 0 C9 1 0.553296 0.098007 0.430848 11.00000 0.06409 0.06236 = 0.03982 -0.00666 0.02482 0.00402 AFIX 43 H9 2 0.550105 0.077060 0.350270 11.00000 -1.20000 AFIX 0 C10 1 0.516699 0.185294 0.446078 11.00000 0.04713 0.05329 = 0.03297 -0.00105 0.01130 0.00067 AFIX 43 H10 2 0.489270 0.222960 0.375580 11.00000 -1.20000 AFIX 0 C11 1 0.365626 0.535481 0.446588 11.00000 0.04454 0.04596 = 0.04658 0.00008 0.00687 0.00498 AFIX 23 H11A 2 0.386896 0.611180 0.434640 11.00000 -1.20000 H11B 2 0.347979 0.577252 0.493784 11.00000 -1.20000 AFIX 0 C12 1 0.325665 0.487223 0.319598 11.00000 0.03649 0.04781 = 0.04136 0.00222 0.01154 0.00833 C13 1 0.299665 0.356574 0.303770 11.00000 0.05589 0.05906 = 0.04636 0.00310 0.01537 -0.00408 AFIX 43 H13 2 0.308117 0.294146 0.372102 11.00000 -1.20000 AFIX 0 C14 1 0.261204 0.316949 0.187812 11.00000 0.05803 0.07567 = 0.06365 -0.01341 0.01668 -0.01447 AFIX 43 H14 2 0.244365 0.227975 0.178605 11.00000 -1.20000 AFIX 0 C15 1 0.247865 0.408625 0.086421 11.00000 0.05849 0.09254 = 0.04479 -0.00944 0.00253 0.01213 AFIX 43 H15 2 0.221441 0.383089 0.009042 11.00000 -1.20000 AFIX 0 C16 1 0.273565 0.537403 0.099729 11.00000 0.08144 0.08442 = 0.04081 0.01464 0.01178 0.02071 AFIX 43 H16 2 0.264876 0.599333 0.030999 11.00000 -1.20000 AFIX 0 C17 1 0.312772 0.576451 0.215890 11.00000 0.05964 0.05622 = 0.05372 0.00992 0.01872 0.00668 AFIX 43 H17 2 0.330483 0.663686 0.223696 11.00000 -1.20000 AFIX 0 C18 1 0.644188 0.009060 0.768071 11.00000 0.05511 0.06587 = 0.05518 0.00979 0.01857 0.01641 AFIX 137 H18A 2 0.637698 -0.091892 0.777173 11.00000 -1.50000 H18B 2 0.647770 0.061290 0.842252 11.00000 -1.50000 H18C 2 0.675571 0.018165 0.756807 11.00000 -1.50000 AFIX 0 HKLF 4 REM TA4151 in C2/c #15 REM R1 = 0.0503 for 2022 Fo > 4sig(Fo) and 0.0599 for all 2466 data REM 174 parameters refined using 0 restraints END WGHT 0.0872 0.3981 REM Highest difference peak 0.220, deepest hole -0.162, 1-sigma level 0.040 Q1 1 0.5000 0.3306 0.7500 10.50000 0.05 0.22 Q2 1 0.4746 0.2869 0.6346 11.00000 0.05 0.20 Q3 1 0.6282 -0.0487 0.8290 11.00000 0.05 0.18 Q4 1 0.4935 0.3888 0.6301 11.00000 0.05 0.18 Q5 1 0.6670 -0.0760 0.7599 11.00000 0.05 0.17 Q6 1 0.3290 0.5158 0.2605 11.00000 0.05 0.17 Q7 1 0.6671 0.1008 0.8198 11.00000 0.05 0.16 Q8 1 0.3007 0.4481 0.3340 11.00000 0.05 0.14 Q9 1 0.4579 0.4048 0.6816 11.00000 0.05 0.14 Q10 1 0.5299 0.1399 0.6184 11.00000 0.05 0.14 Q11 1 0.5481 0.2356 0.6202 11.00000 0.05 0.13 Q12 1 0.6046 0.1157 0.6006 11.00000 0.05 0.13 Q13 1 0.4154 0.5032 0.7060 11.00000 0.05 0.13 Q14 1 0.2856 0.6084 0.0245 11.00000 0.05 0.12 Q15 1 0.2192 0.3043 -0.0385 11.00000 0.05 0.12 Q16 1 0.2726 0.3425 0.1346 11.00000 0.05 0.12 Q17 1 0.6191 0.0243 0.7151 11.00000 0.05 0.12 Q18 1 0.5735 0.0648 0.6569 11.00000 0.05 0.12 Q19 1 0.2789 0.3831 0.3786 11.00000 0.05 0.11 Q20 1 0.3088 0.5509 0.1535 11.00000 0.05 0.11 ; _shelx_res_checksum 87631 _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 1.167 _oxdiff_exptl_absorpt_empirical_full_min 0.863 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 N1 N 0.39918(5) 0.41798(15) 0.52006(13) 0.0420(4) Uani 1 1 d . . . . . C1 C 0.43362(6) 0.36010(19) 0.46644(15) 0.0413(4) Uani 1 1 d . . . . . H1A H 0.4424 0.4350 0.4205 0.050 Uiso 1 1 calc R . . . . H1B H 0.4175 0.2792 0.4102 0.050 Uiso 1 1 calc R . . . . C2 C 0.48117(6) 0.31053(17) 0.58020(14) 0.0371(4) Uani 1 1 d . . . . . C3 C 0.48011(6) 0.36850(17) 0.68407(14) 0.0378(4) Uani 1 1 d . . . . . C4 C 0.43230(6) 0.4603(2) 0.64975(15) 0.0435(4) Uani 1 1 d . . . . . H4A H 0.4155 0.4397 0.7048 0.052 Uiso 1 1 calc R . . . . H4B H 0.4407 0.5631 0.6550 0.052 Uiso 1 1 calc R . . . . C5 C 0.52051(6) 0.21744(18) 0.56620(14) 0.0374(4) Uani 1 1 d . . . . . C6 C 0.56239(6) 0.15769(19) 0.66930(15) 0.0411(4) Uani 1 1 d . . . . . H6 H 0.5654 0.1766 0.7501 0.049 Uiso 1 1 calc R . . . . C7 C 0.59946(7) 0.07129(19) 0.65495(17) 0.0450(4) Uani 1 1 d . . . . . C8 C 0.59445(8) 0.0419(2) 0.53418(19) 0.0524(5) Uani 1 1 d . . . . . H8 H 0.6190 -0.0160 0.5229 0.063 Uiso 1 1 calc R . . . . C9 C 0.55330(8) 0.0980(2) 0.43085(17) 0.0545(5) Uani 1 1 d . . . . . H9 H 0.5501 0.0771 0.3503 0.065 Uiso 1 1 calc R . . . . C10 C 0.51670(7) 0.1853(2) 0.44608(16) 0.0464(4) Uani 1 1 d . . . . . H10 H 0.4893 0.2230 0.3756 0.056 Uiso 1 1 calc R . . . . C11 C 0.36563(7) 0.5355(2) 0.44659(18) 0.0500(5) Uani 1 1 d . . . . . H11A H 0.3869 0.6112 0.4346 0.060 Uiso 1 1 calc R . . . . H11B H 0.3480 0.5773 0.4938 0.060 Uiso 1 1 calc R . . . . C12 C 0.32567(6) 0.4872(2) 0.31960(16) 0.0436(4) Uani 1 1 d . . . . . C13 C 0.29967(8) 0.3566(2) 0.30377(19) 0.0559(5) Uani 1 1 d . . . . . H13 H 0.3081 0.2941 0.3721 0.067 Uiso 1 1 calc R . . . . C14 C 0.26120(9) 0.3169(3) 0.1878(2) 0.0689(6) Uani 1 1 d . . . . . H14 H 0.2444 0.2280 0.1786 0.083 Uiso 1 1 calc R . . . . C15 C 0.24786(9) 0.4086(3) 0.0864(2) 0.0719(7) Uani 1 1 d . . . . . H15 H 0.2214 0.3831 0.0090 0.086 Uiso 1 1 calc R . . . . C16 C 0.27357(10) 0.5374(3) 0.0997(2) 0.0738(7) Uani 1 1 d . . . . . H16 H 0.2649 0.5993 0.0310 0.089 Uiso 1 1 calc R . . . . C17 C 0.31277(8) 0.5765(2) 0.21589(19) 0.0584(5) Uani 1 1 d . . . . . H17 H 0.3305 0.6637 0.2237 0.070 Uiso 1 1 calc R . . . . C18 C 0.64419(8) 0.0091(3) 0.7681(2) 0.0604(6) Uani 1 1 d . . . . . H18A H 0.6377 -0.0919 0.7772 0.091 Uiso 1 1 calc GR . . . . H18B H 0.6478 0.0613 0.8423 0.091 Uiso 1 1 calc GR . . . . H18C H 0.6756 0.0182 0.7568 0.091 Uiso 1 1 calc GR . . . . 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 0.0394(7) 0.0457(8) 0.0335(7) -0.0008(6) 0.0082(6) 0.0035(6) C1 0.0429(8) 0.0453(9) 0.0308(8) 0.0010(7) 0.0111(7) 0.0020(7) C2 0.0370(8) 0.0401(8) 0.0298(7) 0.0027(6) 0.0100(6) -0.0038(6) C3 0.0395(8) 0.0401(8) 0.0312(8) 0.0026(7) 0.0123(7) -0.0017(7) C4 0.0435(9) 0.0473(9) 0.0351(9) -0.0024(7) 0.0123(7) 0.0020(7) C5 0.0388(8) 0.0378(8) 0.0331(8) -0.0006(6) 0.0128(6) -0.0041(6) C6 0.0432(8) 0.0455(9) 0.0332(8) 0.0004(7) 0.0149(7) -0.0015(7) C7 0.0434(9) 0.0431(9) 0.0465(10) 0.0046(8) 0.0171(8) 0.0018(7) C8 0.0558(11) 0.0533(10) 0.0528(11) -0.0022(9) 0.0276(9) 0.0071(8) C9 0.0641(12) 0.0624(12) 0.0398(9) -0.0067(9) 0.0248(9) 0.0040(9) C10 0.0471(9) 0.0533(10) 0.0330(9) -0.0010(8) 0.0113(7) 0.0007(8) C11 0.0445(9) 0.0460(10) 0.0466(10) 0.0001(8) 0.0069(8) 0.0050(8) C12 0.0365(8) 0.0478(10) 0.0414(9) 0.0022(8) 0.0115(7) 0.0083(7) C13 0.0559(11) 0.0591(11) 0.0464(10) 0.0031(9) 0.0154(9) -0.0041(9) C14 0.0580(12) 0.0757(15) 0.0637(13) -0.0134(12) 0.0167(10) -0.0145(11) C15 0.0585(12) 0.0925(18) 0.0448(11) -0.0094(12) 0.0025(9) 0.0121(12) C16 0.0814(15) 0.0844(16) 0.0408(11) 0.0146(11) 0.0118(10) 0.0207(13) C17 0.0596(12) 0.0562(11) 0.0537(12) 0.0099(10) 0.0187(9) 0.0067(9) C18 0.0551(11) 0.0659(13) 0.0552(12) 0.0098(10) 0.0186(10) 0.0164(10) 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 C4 N1 C1 106.77(13) . . ? C11 N1 C1 113.81(14) . . ? C11 N1 C4 112.98(14) . . ? N1 C1 H1A 111.0 . . ? N1 C1 H1B 111.0 . . ? N1 C1 C2 103.95(12) . . ? H1A C1 H1B 109.0 . . ? C2 C1 H1A 111.0 . . ? C2 C1 H1B 111.0 . . ? C3 C2 C1 108.98(14) . . ? C3 C2 C5 130.00(15) . . ? C5 C2 C1 120.99(14) . . ? C2 C3 C3 130.34(17) . 2_656 ? C2 C3 C4 110.23(14) . . ? C3 C3 C4 118.99(14) 2_656 . ? N1 C4 C3 103.93(13) . . ? N1 C4 H4A 111.0 . . ? N1 C4 H4B 111.0 . . ? C3 C4 H4A 111.0 . . ? C3 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? C6 C5 C2 122.71(14) . . ? C10 C5 C2 119.82(15) . . ? C10 C5 C6 117.47(15) . . ? C5 C6 H6 118.9 . . ? C7 C6 C5 122.17(15) . . ? C7 C6 H6 118.9 . . ? C6 C7 C8 118.75(16) . . ? C6 C7 C18 120.80(17) . . ? C8 C7 C18 120.45(17) . . ? C7 C8 H8 119.8 . . ? C9 C8 C7 120.34(17) . . ? C9 C8 H8 119.8 . . ? C8 C9 H9 119.7 . . ? C8 C9 C10 120.54(17) . . ? C10 C9 H9 119.7 . . ? C5 C10 H10 119.6 . . ? C9 C10 C5 120.74(16) . . ? C9 C10 H10 119.6 . . ? N1 C11 H11A 108.9 . . ? N1 C11 H11B 108.9 . . ? N1 C11 C12 113.42(15) . . ? H11A C11 H11B 107.7 . . ? C12 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C13 C12 C11 121.70(17) . . ? C13 C12 C17 118.06(18) . . ? C17 C12 C11 120.20(18) . . ? C12 C13 H13 119.5 . . ? C12 C13 C14 121.1(2) . . ? C14 C13 H13 119.5 . . ? C13 C14 H14 119.9 . . ? C15 C14 C13 120.2(2) . . ? C15 C14 H14 119.9 . . ? C14 C15 H15 120.2 . . ? C16 C15 C14 119.7(2) . . ? C16 C15 H15 120.2 . . ? C15 C16 H16 119.9 . . ? C15 C16 C17 120.2(2) . . ? C17 C16 H16 119.9 . . ? C12 C17 C16 120.8(2) . . ? C12 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C7 C18 H18A 109.5 . . ? C7 C18 H18B 109.5 . . ? C7 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 N1 C1 1.469(2) . ? N1 C4 1.461(2) . ? N1 C11 1.456(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1 C2 1.512(2) . ? C2 C3 1.341(2) . ? C2 C5 1.472(2) . ? C3 C3 1.479(3) 2_656 ? C3 C4 1.503(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.400(2) . ? C5 C10 1.397(2) . ? C6 H6 0.9300 . ? C6 C7 1.386(2) . ? C7 C8 1.388(3) . ? C7 C18 1.508(2) . ? C8 H8 0.9300 . ? C8 C9 1.379(3) . ? C9 H9 0.9300 . ? C9 C10 1.384(3) . ? C10 H10 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.507(2) . ? C12 C13 1.380(3) . ? C12 C17 1.381(3) . ? C13 H13 0.9300 . ? C13 C14 1.384(3) . ? C14 H14 0.9300 . ? C14 C15 1.372(3) . ? C15 H15 0.9300 . ? C15 C16 1.364(4) . ? C16 H16 0.9300 . ? C16 C17 1.393(3) . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 -15.08(18) . . . . ? N1 C1 C2 C5 166.81(14) . . . . ? N1 C11 C12 C13 40.5(2) . . . . ? N1 C11 C12 C17 -141.84(18) . . . . ? C1 N1 C4 C3 -23.90(17) . . . . ? C1 N1 C11 C12 66.9(2) . . . . ? C1 C2 C3 C3 -171.84(13) . . . 2_656 ? C1 C2 C3 C4 0.25(19) . . . . ? C1 C2 C5 C6 -173.62(15) . . . . ? C1 C2 C5 C10 6.1(2) . . . . ? C2 C3 C4 N1 14.76(18) . . . . ? C2 C5 C6 C7 -179.38(16) . . . . ? C2 C5 C10 C9 179.98(16) . . . . ? C3 C2 C5 C6 8.7(3) . . . . ? C3 C2 C5 C10 -171.52(17) . . . . ? C3 C3 C4 N1 -172.13(13) 2_656 . . . ? C4 N1 C1 C2 24.08(17) . . . . ? C4 N1 C11 C12 -171.08(15) . . . . ? C5 C2 C3 C3 6.0(3) . . . 2_656 ? C5 C2 C3 C4 178.13(16) . . . . ? C5 C6 C7 C8 -0.8(3) . . . . ? C5 C6 C7 C18 179.79(17) . . . . ? C6 C5 C10 C9 -0.2(3) . . . . ? C6 C7 C8 C9 0.1(3) . . . . ? C7 C8 C9 C10 0.5(3) . . . . ? C8 C9 C10 C5 -0.4(3) . . . . ? C10 C5 C6 C7 0.8(3) . . . . ? C11 N1 C1 C2 149.44(13) . . . . ? C11 N1 C4 C3 -149.76(15) . . . . ? C11 C12 C13 C14 176.74(19) . . . . ? C11 C12 C17 C16 -175.85(19) . . . . ? C12 C13 C14 C15 -0.8(4) . . . . ? C13 C12 C17 C16 1.9(3) . . . . ? C13 C14 C15 C16 1.6(4) . . . . ? C14 C15 C16 C17 -0.7(4) . . . . ? C15 C16 C17 C12 -1.1(4) . . . . ? C17 C12 C13 C14 -1.0(3) . . . . ? C18 C7 C8 C9 179.52(19) . . . . ?