#------------------------------------------------------------------------------ #$Date: 2024-07-04 07:50:12 +0300 (Thu, 04 Jul 2024) $ #$Revision: 292730 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/20/1572056.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_1572056 loop_ _publ_author_name 'Zhou, Yu-Qiang' 'He, Kui-Cheng' 'Zheng, Wei-Hao' 'Lv, Jing-Fang' 'He, Shi-Mei' 'Yu, Ning' 'Yang, Yun-Bo' 'Liu, Lv-Yan' 'Jiang, Kun' 'Wei, Ye' _publ_section_title ; 1,5-Hydrogen atom transfer of α-iminyl radical cations: a new platform for relay annulation for pyridine derivatives and axially chiral heterobiaryls. ; _journal_issue 20 _journal_name_full 'Chemical science' _journal_page_first 7502 _journal_page_last 7514 _journal_paper_doi 10.1039/d4sc01858c _journal_volume 15 _journal_year 2024 _chemical_formula_moiety '2(C21 H19 N)' _chemical_formula_sum 'C42 H38 N2' _chemical_formula_weight 570.74 _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 iterative _audit_creation_date 2021-04-29 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2023-11-09 deposited with the CCDC. 2024-04-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.672(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.2995(4) _cell_length_b 25.7122(17) _cell_length_c 12.4585(16) _cell_measurement_reflns_used 8115 _cell_measurement_temperature 290.19(10) _cell_measurement_theta_max 71.6550 _cell_measurement_theta_min 3.6400 _cell_volume 3191.7(5) _computing_cell_refinement 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _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 ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_environment air _diffrn_ambient_temperature 290.19(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.0243 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.988 _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 -65.00 36.00 1.00 1.00 -- -35.72 19.00 30.00 101 2 \w -52.00 32.00 1.00 1.00 -- -35.72 57.00 90.00 84 3 \w -103.00 -19.00 1.00 1.00 -- -35.72 -57.00-150.00 84 4 \w -33.00 55.00 1.00 1.00 -- 35.72 -38.00 60.00 88 5 \w 24.00 90.00 1.00 1.00 -- 35.72-126.00 30.00 66 6 \w 1.00 75.00 1.00 1.00 -- 35.72 -99.00 -30.00 74 7 \w 39.00 110.00 1.00 1.17 -- 107.97 -95.00 -90.00 71 8 \w 101.00 178.00 1.00 1.17 -- 107.97 112.00 -30.00 77 9 \w 38.00 129.00 1.00 1.17 -- 107.97 -30.00-150.00 91 10 \w 38.00 112.00 1.00 1.17 -- 107.97-112.00 30.00 74 11 \w 87.00 178.00 1.00 1.17 -- 107.97 30.00 -60.00 91 12 \w 38.00 129.00 1.00 1.17 -- 107.97 -30.00 120.00 91 13 \w 81.00 176.00 1.00 1.17 -- 107.97 77.00-150.00 95 14 \w 40.00 125.00 1.00 1.17 -- 107.97 -45.00 60.00 85 15 \w 40.00 135.00 1.00 1.17 -- 107.97 -77.00 -60.00 95 16 \w -103.00 -9.00 1.00 1.00 -- -35.72 -77.00 120.00 94 17 \w -103.00 -19.00 1.00 1.00 -- -35.72 -57.00 -60.00 84 18 \w -103.00 -19.00 1.00 1.00 -- -35.72 -57.00 30.00 84 19 \w -32.00 52.00 1.00 1.00 -- 35.72 -57.00-180.00 84 20 \w 24.00 90.00 1.00 1.00 -- 35.72-126.00-180.00 66 21 \w 70.00 178.00 1.00 1.17 -- 107.97 15.00 60.00 108 22 \w 70.00 178.00 1.00 1.17 -- 107.97 15.00-180.00 108 23 \w 91.00 176.00 1.00 1.17 -- 107.97 45.00 -30.00 85 24 \w 91.00 176.00 1.00 1.17 -- 107.97 45.00 90.00 85 25 \w 39.00 110.00 1.00 1.17 -- 107.97 -95.00 120.00 71 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, EosS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0072829000 _diffrn_orient_matrix_UB_12 -0.1218067000 _diffrn_orient_matrix_UB_13 0.0055524000 _diffrn_orient_matrix_UB_21 -0.0072283000 _diffrn_orient_matrix_UB_22 0.0099885000 _diffrn_orient_matrix_UB_23 0.0596260000 _diffrn_orient_matrix_UB_31 -0.1542827000 _diffrn_orient_matrix_UB_32 0.0377573000 _diffrn_orient_matrix_UB_33 -0.0030933000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_unetI/netI 0.0265 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 30577 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 71.748 _diffrn_reflns_theta_min 4.051 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.520 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.55655 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) 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 1.188 _exptl_crystal_description prism _exptl_crystal_F_000 1216 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.29 _refine_diff_density_max 0.145 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.033 _refine_ls_extinction_coef 0.0035(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 402 _refine_ls_number_reflns 6172 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0428 _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^)+(0.0584P)^2^+0.5057P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1146 _refine_ls_wR_factor_ref 0.1179 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5627 _reflns_number_total 6172 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL ZYQ-1-2021a in P2(1)/n CELL 1.54184 10.2995 25.7122 12.4585 90 104.672 90 ZERR 4 0.0004 0.0017 0.0016 0 0.007 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N UNIT 168 152 8 L.S. 10 PLAN 20 BOND fmap 2 acta REM REM REM WGHT 0.058400 0.505700 EXTI 0.003510 FVAR 0.15690 N1 3 0.328500 0.060524 0.559844 11.00000 0.04332 0.04743 = 0.04823 0.00197 0.00765 -0.00102 C1 1 0.282246 0.108065 0.529665 11.00000 0.04583 0.05505 = 0.05271 0.00657 0.00502 0.00530 AFIX 43 H1 2 0.198865 0.111041 0.479222 11.00000 -1.20000 AFIX 0 C2 1 0.350437 0.153170 0.568645 11.00000 0.05329 0.04372 = 0.05649 0.00991 0.01246 0.01119 AFIX 43 H2 2 0.312426 0.185372 0.545476 11.00000 -1.20000 AFIX 0 C3 1 0.476805 0.150239 0.643054 11.00000 0.04768 0.03543 = 0.04824 0.00453 0.01755 0.00357 C4 1 0.527855 0.100684 0.676150 11.00000 0.04148 0.03239 = 0.04322 0.00322 0.01289 0.00060 C5 1 0.449920 0.057334 0.632603 11.00000 0.04073 0.03674 = 0.04152 0.00187 0.01176 -0.00100 C6 1 0.499718 0.004728 0.669628 11.00000 0.04124 0.03264 = 0.04724 0.00089 0.01475 -0.00266 C7 1 0.449410 -0.038825 0.605923 11.00000 0.04941 0.04132 = 0.05368 -0.00547 0.01708 -0.00736 AFIX 43 H7 2 0.386768 -0.034552 0.538174 11.00000 -1.20000 AFIX 0 C8 1 0.491466 -0.088195 0.642209 11.00000 0.06166 0.03458 = 0.07378 -0.01032 0.02686 -0.00771 AFIX 43 H8 2 0.458413 -0.116965 0.598572 11.00000 -1.20000 AFIX 0 C9 1 0.582592 -0.094680 0.743314 11.00000 0.06217 0.03145 = 0.08535 0.00638 0.02195 0.00302 AFIX 43 H9 2 0.609251 -0.127958 0.768913 11.00000 -1.20000 AFIX 0 C10 1 0.634616 -0.051793 0.806942 11.00000 0.05511 0.03638 = 0.06636 0.00938 0.01091 0.00166 AFIX 43 H10 2 0.696388 -0.056700 0.874915 11.00000 -1.20000 AFIX 0 C11 1 0.596391 -0.001496 0.771296 11.00000 0.04271 0.03206 = 0.05113 0.00406 0.01389 -0.00069 C12 1 0.651288 0.046436 0.840139 11.00000 0.04524 0.03422 = 0.04573 0.00285 0.00832 -0.00042 C13 1 0.659799 0.090976 0.759911 11.00000 0.04150 0.03208 = 0.05086 0.00296 0.00927 -0.00262 AFIX 23 H13A 2 0.687554 0.122517 0.802215 11.00000 -1.20000 H13B 2 0.727620 0.082624 0.720981 11.00000 -1.20000 AFIX 0 C14 1 0.792098 0.037557 0.916187 11.00000 0.05333 0.04888 = 0.05442 0.00380 0.00202 0.00084 AFIX 137 H14A 2 0.787866 0.011430 0.970242 11.00000 -1.50000 H14B 2 0.825023 0.069449 0.953279 11.00000 -1.50000 H14C 2 0.851455 0.026239 0.872593 11.00000 -1.50000 AFIX 0 C15 1 0.555660 0.061493 0.911537 11.00000 0.06142 0.05502 = 0.05203 -0.00109 0.01836 -0.00081 AFIX 137 H15A 2 0.467025 0.066628 0.864684 11.00000 -1.50000 H15B 2 0.586314 0.093083 0.950909 11.00000 -1.50000 H15C 2 0.553820 0.034187 0.963683 11.00000 -1.50000 AFIX 0 C16 1 0.550227 0.198519 0.688403 11.00000 0.05197 0.03005 = 0.05377 0.00824 0.01855 0.00446 C17 1 0.680115 0.208363 0.681409 11.00000 0.05759 0.03625 = 0.07090 0.00489 0.02805 0.00469 AFIX 43 H17 2 0.722582 0.184907 0.644744 11.00000 -1.20000 AFIX 0 C18 1 0.747301 0.252625 0.728276 11.00000 0.05777 0.04191 = 0.08692 0.01001 0.02440 -0.00396 AFIX 43 H18 2 0.834257 0.258888 0.722630 11.00000 -1.20000 AFIX 0 C19 1 0.685504 0.287550 0.783457 11.00000 0.08145 0.03379 = 0.07785 0.00127 0.02042 -0.00729 AFIX 43 H19 2 0.731407 0.316904 0.816617 11.00000 -1.20000 AFIX 0 C20 1 0.555716 0.278717 0.789146 11.00000 0.08717 0.03743 = 0.08413 -0.00448 0.03873 0.00403 AFIX 43 H20 2 0.513310 0.302499 0.825136 11.00000 -1.20000 AFIX 0 C21 1 0.488093 0.234732 0.741703 11.00000 0.06160 0.03687 = 0.08010 0.00192 0.03291 0.00503 AFIX 43 H21 2 0.400082 0.229264 0.745429 11.00000 -1.20000 AFIX 0 N2 3 -0.075569 0.149407 0.536041 11.00000 0.04996 0.04373 = 0.04599 -0.00195 -0.00076 0.00538 C22 1 -0.124543 0.103253 0.496443 11.00000 0.05200 0.05108 = 0.04608 -0.00913 -0.00560 0.00210 AFIX 43 H22 2 -0.187105 0.102498 0.427967 11.00000 -1.20000 AFIX 0 C23 1 -0.088655 0.056771 0.550146 11.00000 0.04642 0.04197 = 0.04985 -0.01439 0.00161 -0.00323 AFIX 43 H23 2 -0.127264 0.025883 0.518497 11.00000 -1.20000 AFIX 0 C24 1 0.006250 0.056182 0.652653 11.00000 0.03730 0.03315 = 0.04444 -0.00780 0.00822 -0.00157 C25 1 0.058524 0.104201 0.696828 11.00000 0.03631 0.03196 = 0.04128 -0.00454 0.00460 -0.00168 C26 1 0.014745 0.149349 0.635741 11.00000 0.03611 0.03492 = 0.04264 -0.00284 0.00574 0.00190 C27 1 0.069749 0.200523 0.679559 11.00000 0.03622 0.03028 = 0.05066 -0.00108 0.00874 0.00282 C28 1 0.056261 0.243332 0.608435 11.00000 0.05362 0.03721 = 0.05896 0.00508 0.00883 0.00631 AFIX 43 H28 2 0.014914 0.239253 0.533384 11.00000 -1.20000 AFIX 0 C29 1 0.103654 0.291531 0.648467 11.00000 0.06658 0.03256 = 0.07963 0.00990 0.01475 0.00416 AFIX 43 H29 2 0.095054 0.319726 0.600417 11.00000 -1.20000 AFIX 0 C30 1 0.163888 0.297890 0.759955 11.00000 0.05881 0.02753 = 0.08717 -0.00710 0.01608 -0.00266 AFIX 43 H30 2 0.194716 0.330513 0.787179 11.00000 -1.20000 AFIX 0 C31 1 0.178475 0.255970 0.831110 11.00000 0.04969 0.03465 = 0.06182 -0.01042 0.01075 -0.00371 AFIX 43 H31 2 0.218758 0.260773 0.906149 11.00000 -1.20000 AFIX 0 C32 1 0.133987 0.206554 0.792678 11.00000 0.03627 0.03028 = 0.05190 -0.00512 0.00940 -0.00121 C33 1 0.148210 0.159959 0.869691 11.00000 0.05532 0.03472 = 0.04282 -0.00455 0.00203 -0.00900 C34 1 0.163319 0.110321 0.805109 11.00000 0.05059 0.03005 = 0.04619 -0.00183 -0.00476 -0.00269 AFIX 23 H34A 2 0.251284 0.110463 0.790170 11.00000 -1.20000 H34B 2 0.159075 0.080402 0.851523 11.00000 -1.20000 AFIX 0 C35 1 0.023904 0.156492 0.915238 11.00000 0.09455 0.06363 = 0.06683 -0.00835 0.03670 -0.02108 AFIX 137 H35A 2 0.015619 0.187848 0.954804 11.00000 -1.50000 H35B 2 0.032501 0.127306 0.964600 11.00000 -1.50000 H35C 2 -0.054467 0.152144 0.854910 11.00000 -1.50000 AFIX 0 C36 1 0.275061 0.164304 0.966121 11.00000 0.09339 0.04549 = 0.05356 -0.00507 -0.01934 -0.01129 AFIX 137 H36A 2 0.351476 0.170715 0.937091 11.00000 -1.50000 H36B 2 0.288071 0.132425 1.007585 11.00000 -1.50000 H36C 2 0.264779 0.192481 1.013848 11.00000 -1.50000 AFIX 0 C37 1 0.046650 0.005301 0.707470 11.00000 0.04581 0.02952 = 0.04410 -0.01020 0.01077 -0.00368 C38 1 0.180879 -0.008883 0.745452 11.00000 0.04622 0.03840 = 0.04618 -0.00511 0.01018 -0.00116 AFIX 43 H38 2 0.247567 0.014465 0.739271 11.00000 -1.20000 AFIX 0 C39 1 0.216426 -0.057328 0.792344 11.00000 0.06167 0.04317 = 0.04881 -0.00518 0.00966 0.00965 AFIX 43 H39 2 0.306480 -0.066494 0.816439 11.00000 -1.20000 AFIX 0 C40 1 0.118340 -0.092009 0.803344 11.00000 0.08974 0.03234 = 0.05748 -0.00127 0.02065 0.00470 AFIX 43 H40 2 0.142127 -0.124277 0.836174 11.00000 -1.20000 AFIX 0 C41 1 -0.014585 -0.078659 0.765589 11.00000 0.07659 0.03463 = 0.07908 -0.00868 0.03072 -0.01299 AFIX 43 H41 2 -0.080710 -0.102062 0.772785 11.00000 -1.20000 AFIX 0 C42 1 -0.050874 -0.030690 0.716958 11.00000 0.05112 0.03582 = 0.06881 -0.01274 0.01767 -0.00792 AFIX 43 H42 2 -0.141218 -0.022398 0.690357 11.00000 -1.20000 AFIX 0 HKLF 4 REM ZYQ-1-2021a in P2(1)/n REM R1 = 0.0428 for 5627 Fo > 4sig(Fo) and 0.0463 for all 6172 data REM 402 parameters refined using 0 restraints END WGHT 0.0584 0.5057 REM Highest difference peak 0.145, deepest hole -0.175, 1-sigma level 0.033 Q1 1 0.2653 0.0160 0.6965 11.00000 0.05 0.14 Q2 1 0.1465 0.1856 0.8328 11.00000 0.05 0.13 Q3 1 0.0391 0.1773 0.6594 11.00000 0.05 0.13 Q4 1 0.2331 0.1381 1.0268 11.00000 0.05 0.12 Q5 1 0.1578 0.1375 0.8430 11.00000 0.05 0.12 Q6 1 0.1412 0.2331 0.8140 11.00000 0.05 0.12 Q7 1 0.0833 0.1601 0.8824 11.00000 0.05 0.12 Q8 1 0.4872 0.0797 0.6661 11.00000 0.05 0.12 Q9 1 0.4413 0.0565 0.8748 11.00000 0.05 0.12 Q10 1 0.6820 0.2799 0.7185 11.00000 0.05 0.11 Q11 1 0.3323 0.1271 0.9881 11.00000 0.05 0.11 Q12 1 0.2134 0.1903 1.0312 11.00000 0.05 0.11 Q13 1 -0.0030 -0.0061 0.7173 11.00000 0.05 0.11 Q14 1 0.5424 0.2049 0.7386 11.00000 0.05 0.11 Q15 1 0.1083 0.2032 0.7431 11.00000 0.05 0.11 Q16 1 0.3036 0.1340 0.5693 11.00000 0.05 0.11 Q17 1 0.5379 0.1077 0.9052 11.00000 0.05 0.11 Q18 1 -0.1568 -0.0011 0.7230 11.00000 0.05 0.10 Q19 1 0.3191 0.2012 0.5743 11.00000 0.05 0.10 Q20 1 0.5766 -0.0263 0.8017 11.00000 0.05 0.10 REM The information below was added by Olex2. REM REM R1 = 0.0428 for 5627 Fo > 4sig(Fo) and 0.0463 for all 31006 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.14, deepest hole -0.17 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0463 REM R1_gt = 0.0428 REM wR_ref = 0.1179 REM GOOF = 1.057 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 31006 REM Reflections_gt = 5627 REM Parameters = n/a REM Hole = -0.17 REM Peak = 0.14 REM Flack = n/a ; _cod_data_source_file d4sc01858c2.cif _cod_data_source_block zyq-1-2021 _cod_database_code 1572056 _shelxl_version_number 2014-1 _chemical_oxdiff_usercomment 'C1 H1 N1' _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. ; _reflns_odcompleteness_completeness 99.18 _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: C13(H13A,H13B), C34(H34A,H34B) 2.b Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C7(H7), C8(H8), C9(H9), C10(H10), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C28(H28), C29(H29), C30(H30), C31(H31), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42) 2.c Idealised Me refined as rotating group: C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C35(H35A,H35B,H35C), C36(H36A,H36B, H36C) ; _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 1.721 _oxdiff_exptl_absorpt_empirical_full_min 0.574 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 0.32850(11) 0.06052(4) 0.55984(9) 0.0470(3) Uani 1 1 d . . . . . C1 C 0.28225(14) 0.10807(5) 0.52967(11) 0.0525(3) Uani 1 1 d . . . . . H1 H 0.1989 0.1110 0.4792 0.063 Uiso 1 1 calc R . . . . C2 C 0.35044(14) 0.15317(5) 0.56865(11) 0.0514(3) Uani 1 1 d . . . . . H2 H 0.3124 0.1854 0.5455 0.062 Uiso 1 1 calc R . . . . C3 C 0.47681(13) 0.15024(4) 0.64305(10) 0.0428(3) Uani 1 1 d . . . . . C4 C 0.52785(12) 0.10068(4) 0.67615(10) 0.0386(3) Uani 1 1 d . . . . . C5 C 0.44992(12) 0.05733(4) 0.63260(10) 0.0394(3) Uani 1 1 d . . . . . C6 C 0.49972(12) 0.00473(4) 0.66963(10) 0.0397(3) Uani 1 1 d . . . . . C7 C 0.44941(13) -0.03883(5) 0.60592(11) 0.0474(3) Uani 1 1 d . . . . . H7 H 0.3868 -0.0346 0.5382 0.057 Uiso 1 1 calc R . . . . C8 C 0.49147(15) -0.08820(5) 0.64221(13) 0.0549(3) Uani 1 1 d . . . . . H8 H 0.4584 -0.1170 0.5986 0.066 Uiso 1 1 calc R . . . . C9 C 0.58259(15) -0.09468(5) 0.74331(14) 0.0591(4) Uani 1 1 d . . . . . H9 H 0.6093 -0.1280 0.7689 0.071 Uiso 1 1 calc R . . . . C10 C 0.63462(14) -0.05179(5) 0.80694(13) 0.0534(3) Uani 1 1 d . . . . . H10 H 0.6964 -0.0567 0.8749 0.064 Uiso 1 1 calc R . . . . C11 C 0.59639(12) -0.00150(4) 0.77130(10) 0.0416(3) Uani 1 1 d . . . . . C12 C 0.65129(12) 0.04644(4) 0.84014(10) 0.0423(3) Uani 1 1 d . . . . . C13 C 0.65980(12) 0.09098(4) 0.75991(10) 0.0419(3) Uani 1 1 d . . . . . H13A H 0.6876 0.1225 0.8022 0.050 Uiso 1 1 calc R . . . . H13B H 0.7276 0.0826 0.7210 0.050 Uiso 1 1 calc R . . . . C14 C 0.79210(14) 0.03756(5) 0.91619(12) 0.0543(3) Uani 1 1 d . . . . . H14A H 0.7879 0.0114 0.9702 0.081 Uiso 1 1 calc GR . . . . H14B H 0.8250 0.0694 0.9533 0.081 Uiso 1 1 calc GR . . . . H14C H 0.8515 0.0262 0.8726 0.081 Uiso 1 1 calc GR . . . . C15 C 0.55566(15) 0.06149(6) 0.91154(12) 0.0554(3) Uani 1 1 d . . . . . H15A H 0.4670 0.0666 0.8647 0.083 Uiso 1 1 calc GR . . . . H15B H 0.5863 0.0931 0.9509 0.083 Uiso 1 1 calc GR . . . . H15C H 0.5538 0.0342 0.9637 0.083 Uiso 1 1 calc GR . . . . C16 C 0.55023(13) 0.19852(4) 0.68840(11) 0.0443(3) Uani 1 1 d . . . . . C17 C 0.68011(14) 0.20836(5) 0.68141(12) 0.0528(3) Uani 1 1 d . . . . . H17 H 0.7226 0.1849 0.6447 0.063 Uiso 1 1 calc R . . . . C18 C 0.74730(15) 0.25262(5) 0.72828(14) 0.0611(4) Uani 1 1 d . . . . . H18 H 0.8343 0.2589 0.7226 0.073 Uiso 1 1 calc R . . . . C19 C 0.68550(18) 0.28755(5) 0.78346(14) 0.0643(4) Uani 1 1 d . . . . . H19 H 0.7314 0.3169 0.8166 0.077 Uiso 1 1 calc R . . . . C20 C 0.55572(18) 0.27872(5) 0.78915(14) 0.0665(4) Uani 1 1 d . . . . . H20 H 0.5133 0.3025 0.8251 0.080 Uiso 1 1 calc R . . . . C21 C 0.48809(15) 0.23473(5) 0.74170(13) 0.0568(4) Uani 1 1 d . . . . . H21 H 0.4001 0.2293 0.7454 0.068 Uiso 1 1 calc R . . . . N2 N -0.07557(11) 0.14941(4) 0.53604(9) 0.0489(3) Uani 1 1 d . . . . . C22 C -0.12454(14) 0.10325(5) 0.49644(11) 0.0530(3) Uani 1 1 d . . . . . H22 H -0.1871 0.1025 0.4280 0.064 Uiso 1 1 calc R . . . . C23 C -0.08865(13) 0.05677(5) 0.55015(11) 0.0480(3) Uani 1 1 d . . . . . H23 H -0.1273 0.0259 0.5185 0.058 Uiso 1 1 calc R . . . . C24 C 0.00625(12) 0.05618(4) 0.65265(10) 0.0387(3) Uani 1 1 d . . . . . C25 C 0.05852(11) 0.10420(4) 0.69683(9) 0.0375(2) Uani 1 1 d . . . . . C26 C 0.01475(11) 0.14935(4) 0.63574(10) 0.0387(3) Uani 1 1 d . . . . . C27 C 0.06975(11) 0.20052(4) 0.67956(10) 0.0395(3) Uani 1 1 d . . . . . C28 C 0.05626(14) 0.24333(5) 0.60843(12) 0.0509(3) Uani 1 1 d . . . . . H28 H 0.0149 0.2393 0.5334 0.061 Uiso 1 1 calc R . . . . C29 C 0.10365(16) 0.29153(5) 0.64847(14) 0.0603(4) Uani 1 1 d . . . . . H29 H 0.0951 0.3197 0.6004 0.072 Uiso 1 1 calc R . . . . C30 C 0.16389(15) 0.29789(5) 0.75996(14) 0.0583(4) Uani 1 1 d . . . . . H30 H 0.1947 0.3305 0.7872 0.070 Uiso 1 1 calc R . . . . C31 C 0.17847(13) 0.25597(5) 0.83111(12) 0.0493(3) Uani 1 1 d . . . . . H31 H 0.2188 0.2608 0.9061 0.059 Uiso 1 1 calc R . . . . C32 C 0.13399(12) 0.20655(4) 0.79268(10) 0.0398(3) Uani 1 1 d . . . . . C33 C 0.14821(13) 0.15996(5) 0.86969(10) 0.0462(3) Uani 1 1 d . . . . . C34 C 0.16332(13) 0.11032(4) 0.80511(10) 0.0453(3) Uani 1 1 d . . . . . H34A H 0.2513 0.1105 0.7902 0.054 Uiso 1 1 calc R . . . . H34B H 0.1591 0.0804 0.8515 0.054 Uiso 1 1 calc R . . . . C35 C 0.02390(19) 0.15649(6) 0.91524(14) 0.0721(5) Uani 1 1 d . . . . . H35A H 0.0156 0.1878 0.9548 0.108 Uiso 1 1 calc GR . . . . H35B H 0.0325 0.1273 0.9646 0.108 Uiso 1 1 calc GR . . . . H35C H -0.0545 0.1521 0.8549 0.108 Uiso 1 1 calc GR . . . . C36 C 0.27506(19) 0.16430(6) 0.96612(12) 0.0710(5) Uani 1 1 d . . . . . H36A H 0.3515 0.1707 0.9371 0.106 Uiso 1 1 calc GR . . . . H36B H 0.2881 0.1324 1.0076 0.106 Uiso 1 1 calc GR . . . . H36C H 0.2648 0.1925 1.0138 0.106 Uiso 1 1 calc GR . . . . C37 C 0.04665(12) 0.00530(4) 0.70747(10) 0.0399(3) Uani 1 1 d . . . . . C38 C 0.18088(13) -0.00888(5) 0.74545(10) 0.0439(3) Uani 1 1 d . . . . . H38 H 0.2476 0.0145 0.7393 0.053 Uiso 1 1 calc R . . . . C39 C 0.21643(15) -0.05733(5) 0.79234(11) 0.0520(3) Uani 1 1 d . . . . . H39 H 0.3065 -0.0665 0.8164 0.062 Uiso 1 1 calc R . . . . C40 C 0.11834(17) -0.09201(5) 0.80334(12) 0.0595(4) Uani 1 1 d . . . . . H40 H 0.1421 -0.1243 0.8362 0.071 Uiso 1 1 calc R . . . . C41 C -0.01458(17) -0.07866(5) 0.76559(13) 0.0614(4) Uani 1 1 d . . . . . H41 H -0.0807 -0.1021 0.7728 0.074 Uiso 1 1 calc R . . . . C42 C -0.05087(14) -0.03069(5) 0.71696(12) 0.0515(3) Uani 1 1 d . . . . . H42 H -0.1412 -0.0224 0.6904 0.062 Uiso 1 1 calc R . . . . 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 0.0433(6) 0.0474(6) 0.0482(6) 0.0020(4) 0.0076(5) -0.0010(5) C1 0.0458(7) 0.0551(8) 0.0527(7) 0.0066(6) 0.0050(6) 0.0053(6) C2 0.0533(8) 0.0437(7) 0.0565(7) 0.0099(5) 0.0125(6) 0.0112(6) C3 0.0477(7) 0.0354(6) 0.0482(6) 0.0045(5) 0.0175(5) 0.0036(5) C4 0.0415(6) 0.0324(5) 0.0432(6) 0.0032(4) 0.0129(5) 0.0006(5) C5 0.0407(6) 0.0367(6) 0.0415(6) 0.0019(4) 0.0118(5) -0.0010(5) C6 0.0412(6) 0.0326(6) 0.0472(6) 0.0009(5) 0.0147(5) -0.0027(5) C7 0.0494(7) 0.0413(6) 0.0537(7) -0.0055(5) 0.0171(6) -0.0074(5) C8 0.0617(8) 0.0346(6) 0.0738(9) -0.0103(6) 0.0269(7) -0.0077(6) C9 0.0622(9) 0.0314(6) 0.0853(10) 0.0064(6) 0.0220(8) 0.0030(6) C10 0.0551(8) 0.0364(6) 0.0664(8) 0.0094(6) 0.0109(7) 0.0017(6) C11 0.0427(6) 0.0321(6) 0.0511(7) 0.0041(5) 0.0139(5) -0.0007(5) C12 0.0452(6) 0.0342(6) 0.0457(6) 0.0028(5) 0.0083(5) -0.0004(5) C13 0.0415(6) 0.0321(5) 0.0509(6) 0.0030(5) 0.0093(5) -0.0026(5) C14 0.0533(8) 0.0489(7) 0.0544(7) 0.0038(6) 0.0020(6) 0.0008(6) C15 0.0614(8) 0.0550(8) 0.0520(7) -0.0011(6) 0.0184(6) -0.0008(6) C16 0.0520(7) 0.0301(5) 0.0538(7) 0.0082(5) 0.0185(6) 0.0045(5) C17 0.0576(8) 0.0362(6) 0.0709(8) 0.0049(6) 0.0281(7) 0.0047(6) C18 0.0578(8) 0.0419(7) 0.0869(11) 0.0100(7) 0.0244(8) -0.0040(6) C19 0.0814(11) 0.0338(7) 0.0779(10) 0.0013(6) 0.0204(8) -0.0073(7) C20 0.0872(11) 0.0374(7) 0.0841(11) -0.0045(7) 0.0387(9) 0.0040(7) C21 0.0616(8) 0.0369(6) 0.0801(9) 0.0019(6) 0.0329(8) 0.0050(6) N2 0.0500(6) 0.0437(6) 0.0460(6) -0.0020(4) -0.0008(5) 0.0054(5) C22 0.0520(8) 0.0511(7) 0.0461(7) -0.0091(6) -0.0056(6) 0.0021(6) C23 0.0464(7) 0.0420(6) 0.0499(7) -0.0144(5) 0.0016(5) -0.0032(5) C24 0.0373(6) 0.0331(6) 0.0444(6) -0.0078(4) 0.0082(5) -0.0016(4) C25 0.0363(6) 0.0320(5) 0.0413(6) -0.0045(4) 0.0046(5) -0.0017(4) C26 0.0361(6) 0.0349(6) 0.0426(6) -0.0028(4) 0.0057(5) 0.0019(4) C27 0.0362(6) 0.0303(5) 0.0507(6) -0.0011(5) 0.0087(5) 0.0028(4) C28 0.0536(7) 0.0372(6) 0.0590(7) 0.0051(5) 0.0088(6) 0.0063(5) C29 0.0666(9) 0.0326(6) 0.0796(10) 0.0099(6) 0.0148(8) 0.0042(6) C30 0.0588(8) 0.0275(6) 0.0872(10) -0.0071(6) 0.0161(8) -0.0027(5) C31 0.0497(7) 0.0346(6) 0.0618(8) -0.0104(5) 0.0108(6) -0.0037(5) C32 0.0363(6) 0.0303(5) 0.0519(6) -0.0051(5) 0.0094(5) -0.0012(4) C33 0.0553(7) 0.0347(6) 0.0428(6) -0.0046(5) 0.0020(5) -0.0090(5) C34 0.0506(7) 0.0300(5) 0.0462(6) -0.0018(5) -0.0048(5) -0.0027(5) C35 0.0945(13) 0.0636(9) 0.0668(9) -0.0083(7) 0.0367(9) -0.0211(9) C36 0.0934(12) 0.0455(7) 0.0536(8) -0.0051(6) -0.0193(8) -0.0113(8) C37 0.0458(6) 0.0295(5) 0.0441(6) -0.0102(4) 0.0108(5) -0.0037(5) C38 0.0462(7) 0.0384(6) 0.0462(6) -0.0051(5) 0.0102(5) -0.0012(5) C39 0.0617(8) 0.0432(7) 0.0488(7) -0.0052(5) 0.0097(6) 0.0096(6) C40 0.0897(11) 0.0323(6) 0.0575(8) -0.0013(5) 0.0206(8) 0.0047(7) C41 0.0766(10) 0.0346(7) 0.0791(10) -0.0087(6) 0.0307(8) -0.0130(7) C42 0.0511(7) 0.0358(6) 0.0688(8) -0.0127(6) 0.0177(6) -0.0079(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 C5 116.77(11) . . ? N1 C1 C2 123.98(12) . . ? C1 C2 C3 119.65(11) . . ? C2 C3 C4 117.53(11) . . ? C2 C3 C16 120.38(11) . . ? C4 C3 C16 122.03(11) . . ? C3 C4 C13 124.00(10) . . ? C5 C4 C3 118.34(11) . . ? C5 C4 C13 117.61(10) . . ? N1 C5 C4 123.72(11) . . ? N1 C5 C6 117.05(10) . . ? C4 C5 C6 119.20(10) . . ? C7 C6 C5 120.51(11) . . ? C7 C6 C11 119.80(11) . . ? C11 C6 C5 119.67(10) . . ? C8 C7 C6 120.78(13) . . ? C9 C8 C7 119.72(12) . . ? C8 C9 C10 120.17(12) . . ? C9 C10 C11 121.36(13) . . ? C6 C11 C12 119.39(10) . . ? C10 C11 C6 118.11(11) . . ? C10 C11 C12 122.46(11) . . ? C11 C12 C13 108.08(10) . . ? C11 C12 C14 112.61(10) . . ? C11 C12 C15 109.19(10) . . ? C14 C12 C13 108.15(10) . . ? C15 C12 C13 109.86(10) . . ? C15 C12 C14 108.93(11) . . ? C4 C13 C12 112.52(10) . . ? C17 C16 C3 122.29(11) . . ? C17 C16 C21 118.44(12) . . ? C21 C16 C3 119.26(12) . . ? C18 C17 C16 120.79(13) . . ? C19 C18 C17 120.09(14) . . ? C20 C19 C18 119.67(14) . . ? C19 C20 C21 120.32(14) . . ? C20 C21 C16 120.66(14) . . ? C22 N2 C26 116.55(10) . . ? N2 C22 C23 124.32(11) . . ? C22 C23 C24 119.60(11) . . ? C23 C24 C25 117.32(10) . . ? C23 C24 C37 118.63(10) . . ? C25 C24 C37 124.05(10) . . ? C24 C25 C34 124.04(10) . . ? C26 C25 C24 118.58(10) . . ? C26 C25 C34 117.35(9) . . ? N2 C26 C25 123.61(10) . . ? N2 C26 C27 116.63(10) . . ? C25 C26 C27 119.75(10) . . ? C28 C27 C26 119.91(11) . . ? C28 C27 C32 119.65(11) . . ? C32 C27 C26 120.43(10) . . ? C29 C28 C27 120.63(13) . . ? C28 C29 C30 119.90(13) . . ? C31 C30 C29 120.15(12) . . ? C30 C31 C32 121.25(13) . . ? C27 C32 C33 119.47(10) . . ? C31 C32 C27 118.38(11) . . ? C31 C32 C33 122.10(11) . . ? C32 C33 C34 109.30(10) . . ? C32 C33 C35 108.95(11) . . ? C32 C33 C36 111.28(10) . . ? C34 C33 C36 106.88(11) . . ? C35 C33 C34 110.56(11) . . ? C35 C33 C36 109.86(13) . . ? C25 C34 C33 114.24(10) . . ? C38 C37 C24 121.70(11) . . ? C38 C37 C42 118.21(11) . . ? C42 C37 C24 120.01(11) . . ? C39 C38 C37 120.85(12) . . ? C40 C39 C38 120.07(13) . . ? C41 C40 C39 119.71(13) . . ? C40 C41 C42 120.54(13) . . ? C41 C42 C37 120.60(13) . . ? 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 1.3311(16) . ? N1 C5 1.3484(16) . ? C1 C2 1.3789(19) . ? C2 C3 1.3956(18) . ? C3 C4 1.4001(15) . ? C3 C16 1.4885(17) . ? C4 C5 1.4002(16) . ? C4 C13 1.5099(16) . ? C5 C6 1.4784(15) . ? C6 C7 1.3943(16) . ? C6 C11 1.4080(17) . ? C7 C8 1.3799(18) . ? C8 C9 1.377(2) . ? C9 C10 1.3843(19) . ? C10 C11 1.3915(16) . ? C11 C12 1.5259(16) . ? C12 C13 1.5371(16) . ? C12 C14 1.5353(17) . ? C12 C15 1.5346(18) . ? C16 C17 1.3858(18) . ? C16 C21 1.3902(18) . ? C17 C18 1.3821(19) . ? C18 C19 1.380(2) . ? C19 C20 1.375(2) . ? C20 C21 1.380(2) . ? N2 C22 1.3342(16) . ? N2 C26 1.3501(15) . ? C22 C23 1.3738(18) . ? C23 C24 1.3980(17) . ? C24 C25 1.4025(14) . ? C24 C37 1.4856(16) . ? C25 C26 1.3987(15) . ? C25 C34 1.5073(15) . ? C26 C27 1.4811(15) . ? C27 C28 1.3978(17) . ? C27 C32 1.4055(17) . ? C28 C29 1.3782(18) . ? C29 C30 1.380(2) . ? C30 C31 1.3794(19) . ? C31 C32 1.3937(15) . ? C32 C33 1.5186(16) . ? C33 C34 1.5375(16) . ? C33 C35 1.529(2) . ? C33 C36 1.5387(18) . ? C37 C38 1.3917(17) . ? C37 C42 1.3926(17) . ? C38 C39 1.3851(17) . ? C39 C40 1.380(2) . ? C40 C41 1.374(2) . ? C41 C42 1.383(2) . ?