#------------------------------------------------------------------------------ #$Date: 2014-12-24 13:14:38 +0200 (Wed, 24 Dec 2014) $ #$Revision: 129035 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/60/7116087.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_7116087 loop_ _publ_author_name 'Xihong Liu' 'Jinlong Zhang' 'Shixiong Ma' 'Yunxia Ma' 'Rui Wang' _publ_section_title ; Oxidative cross-dehydrogenative coupling between N-aryl tetrahydroisoquinolins and 5H-oxazol-4-ones through two methodologies: copper catalysis or a metal-free strategy ; _journal_name_full Chem.Commun. _journal_page_first 15714 _journal_paper_doi 10.1039/C4cc04508D _journal_volume 50 _journal_year 2014 _chemical_formula_moiety 'C32 H28 N2 O2' _chemical_formula_sum 'C32 H28 N2 O2' _chemical_formula_weight 472.56 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2014-03-10 _audit_creation_method ; Olex2 1.2 (compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781) ; _cell_angle_alpha 90 _cell_angle_beta 94.884(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.5198(3) _cell_length_b 16.3244(7) _cell_length_c 24.2413(9) _cell_measurement_reflns_used 2666 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 22.6710 _cell_measurement_theta_min 3.8270 _cell_volume 2570.68(19) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.885 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0117501000 _diffrn_orient_matrix_UB_12 -0.0322053000 _diffrn_orient_matrix_UB_13 -0.0196603000 _diffrn_orient_matrix_UB_21 0.0433167000 _diffrn_orient_matrix_UB_22 0.0251394000 _diffrn_orient_matrix_UB_23 -0.0198500000 _diffrn_orient_matrix_UB_31 0.0995747000 _diffrn_orient_matrix_UB_32 -0.0147309000 _diffrn_orient_matrix_UB_33 0.0090632000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_unetI/netI 0.0576 _diffrn_reflns_laue_measured_fraction_full 0.999 _diffrn_reflns_laue_measured_fraction_max 0.885 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 10786 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.885 _diffrn_reflns_theta_full 25.500 _diffrn_reflns_theta_max 28.477 _diffrn_reflns_theta_min 3.012 _diffrn_source 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.56560 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.221 _exptl_crystal_description block _exptl_crystal_F_000 1000 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.155 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.035 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 326 _refine_ls_number_reflns 5764 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.073 _refine_ls_R_factor_all 0.1122 _refine_ls_R_factor_gt 0.0667 _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^)+(0.0532P)^2^+0.6680P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1549 _refine_ls_wR_factor_ref 0.1843 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3293 _reflns_number_total 5764 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file c4cc04508d2.cif _[local]_cod_data_source_block liuxh0307 _cod_original_cell_volume 2570.66(18) _cod_database_code 7116087 _shelxl_version_number 2013-2 _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 99.82 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _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 Ternary CH refined with riding coordinates: C9(H9) 2.b Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C2(H2A,H2B), C18(H18A,H18B) 2.c Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32) 2.d Idealised Me refined as rotating group: C16(H16A,H16B,H16C) ; _shelx_res_file ; TITL liuxh0307 in P2(1)/c CELL 0.71073 6.519767 16.324384 24.241318 90 94.884 90 ZERR 4 0.000251 0.00071 0.000933 0 0.0035 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 128 112 8 8 L.S. 20 PLAN 20 BOND $H HTAB MORE -1 CONF fmap 2 acta 51.0 REM D:/olex2_liuxh0307/liuxh0307.hkl WGHT 0.053200 0.668000 FVAR 5.94897 O1 4 0.128209 0.686000 0.153364 11.00000 0.05120 0.05910 = 0.03627 -0.00037 0.00149 0.00412 O2 4 0.651382 0.730534 0.173411 11.00000 0.05318 0.10561 = 0.06908 0.00069 0.00625 -0.00582 N1 3 0.206027 0.673355 0.287026 11.00000 0.04650 0.08452 = 0.03999 0.00462 0.00596 0.00533 N2 3 0.405882 0.688508 0.103732 11.00000 0.06179 0.08258 = 0.04306 0.00150 0.01144 0.00588 C1 1 -0.006260 0.646092 0.276618 11.00000 0.05174 0.12330 = 0.05929 0.02226 0.00297 0.00129 AFIX 23 H1A 2 -0.065586 0.670155 0.242308 11.00000 -1.20000 H1B 2 -0.085031 0.665237 0.306269 11.00000 -1.20000 AFIX 0 C2 1 -0.022199 0.555707 0.272778 11.00000 0.08137 0.12350 = 0.07225 0.02088 -0.00463 -0.03388 AFIX 23 H2A 2 -0.160538 0.540888 0.258329 11.00000 -1.20000 H2B 2 0.002069 0.532320 0.309539 11.00000 -1.20000 AFIX 0 C3 1 0.130067 0.520196 0.235916 11.00000 0.11007 0.06806 = 0.05735 0.01596 -0.02063 -0.01583 C4 1 0.107414 0.440875 0.215672 11.00000 0.20062 0.07760 = 0.08164 0.01789 -0.03397 -0.03912 AFIX 43 H4 2 -0.008385 0.410930 0.223132 11.00000 -1.20000 AFIX 0 C5 1 0.250445 0.405444 0.185064 11.00000 0.24777 0.06383 = 0.08012 0.00423 -0.03699 0.00761 AFIX 43 H5 2 0.230836 0.352133 0.172149 11.00000 -1.20000 AFIX 0 C6 1 0.421948 0.448013 0.173383 11.00000 0.18435 0.08125 = 0.06745 -0.00376 -0.02128 0.05164 AFIX 43 H6 2 0.520285 0.423576 0.153127 11.00000 -1.20000 AFIX 0 C7 1 0.448337 0.528712 0.192168 11.00000 0.11046 0.07823 = 0.05316 -0.00313 -0.01113 0.03202 AFIX 43 H7 2 0.563964 0.558257 0.184050 11.00000 -1.20000 AFIX 0 C8 1 0.301901 0.564882 0.222981 11.00000 0.08177 0.05896 = 0.04318 0.00817 -0.01122 0.01207 C9 1 0.330402 0.652826 0.241790 11.00000 0.04806 0.06414 = 0.03983 0.00032 0.00161 0.00624 AFIX 13 H9 2 0.474720 0.658600 0.256210 11.00000 -1.20000 AFIX 0 C10 1 0.299514 0.675054 0.341683 11.00000 0.05630 0.06327 = 0.04341 0.00292 0.00613 0.01007 C11 1 0.198004 0.649702 0.386794 11.00000 0.07101 0.09371 = 0.05012 0.00444 0.01645 0.00092 AFIX 43 H11 2 0.063734 0.630230 0.381432 11.00000 -1.20000 AFIX 0 C12 1 0.296225 0.653303 0.439933 11.00000 0.10404 0.09453 = 0.04297 0.00559 0.01987 0.01387 AFIX 43 H12 2 0.224421 0.636384 0.469462 11.00000 -1.20000 AFIX 0 C13 1 0.494164 0.680687 0.450687 11.00000 0.10023 0.07247 = 0.04228 -0.00650 -0.00002 0.01817 C14 1 0.591620 0.707476 0.405940 11.00000 0.07771 0.07862 = 0.05484 -0.01094 -0.00403 0.00007 AFIX 43 H14 2 0.725143 0.727641 0.411665 11.00000 -1.20000 AFIX 0 C15 1 0.496962 0.705359 0.352509 11.00000 0.06809 0.07393 = 0.04431 -0.00254 0.00368 -0.00413 AFIX 43 H15 2 0.567602 0.724688 0.323401 11.00000 -1.20000 AFIX 0 C16 1 0.602246 0.680579 0.508607 11.00000 0.15218 0.12043 = 0.04526 -0.01236 -0.01551 0.03334 AFIX 137 H16A 2 0.744559 0.694569 0.506850 11.00000 -1.50000 H16B 2 0.592269 0.627092 0.524621 11.00000 -1.50000 H16C 2 0.538336 0.720007 0.531018 11.00000 -1.50000 AFIX 0 C17 1 0.294801 0.713700 0.192549 11.00000 0.05028 0.05483 = 0.03792 -0.00056 0.00015 0.00155 C18 1 0.247179 0.800471 0.211081 11.00000 0.07287 0.06045 = 0.05099 -0.00416 0.00455 0.00420 AFIX 23 H18A 2 0.116493 0.799736 0.227440 11.00000 -1.20000 H18B 2 0.352073 0.816753 0.239766 11.00000 -1.20000 AFIX 0 C19 1 0.236457 0.864152 0.166112 11.00000 0.07094 0.04842 = 0.04934 -0.00508 0.00295 -0.00012 C20 1 0.401322 0.915505 0.159593 11.00000 0.07442 0.06544 = 0.07742 -0.00570 -0.00101 -0.00534 AFIX 43 H20 2 0.521048 0.909854 0.183022 11.00000 -1.20000 AFIX 0 C21 1 0.391677 0.974842 0.119090 11.00000 0.10802 0.06212 = 0.09462 0.00013 0.01872 -0.01388 AFIX 43 H21 2 0.503406 1.009300 0.115573 11.00000 -1.20000 AFIX 0 C22 1 0.217325 0.982857 0.084115 11.00000 0.14316 0.06510 = 0.06698 0.01001 0.00510 -0.00316 AFIX 43 H22 2 0.210819 1.022314 0.056348 11.00000 -1.20000 AFIX 0 C23 1 0.052639 0.932970 0.089906 11.00000 0.11685 0.06501 = 0.06888 -0.00228 -0.02322 0.00680 AFIX 43 H23 2 -0.066170 0.939031 0.066174 11.00000 -1.20000 AFIX 0 C24 1 0.060314 0.873563 0.130609 11.00000 0.08015 0.05795 = 0.06855 -0.00321 -0.00641 -0.00259 AFIX 43 H24 2 -0.052885 0.839896 0.134152 11.00000 -1.20000 AFIX 0 C25 1 0.475547 0.713084 0.157044 11.00000 0.05649 0.06747 = 0.04844 0.00599 0.00696 0.00341 C26 1 0.211523 0.673974 0.105361 11.00000 0.05973 0.05593 = 0.03959 0.00356 0.00453 0.01262 C27 1 0.072668 0.644655 0.059166 11.00000 0.07156 0.06317 = 0.04387 -0.00703 -0.00563 0.01548 C28 1 0.139712 0.642065 0.006341 11.00000 0.10090 0.10320 = 0.04868 -0.00609 0.00078 0.01662 AFIX 43 H28 2 0.271315 0.660029 0.000313 11.00000 -1.20000 AFIX 0 C29 1 0.010381 0.612764 -0.037088 11.00000 0.13590 0.13703 = 0.04509 -0.01622 -0.01235 0.02895 AFIX 43 H29 2 0.054505 0.611442 -0.072563 11.00000 -1.20000 AFIX 0 C30 1 -0.182772 0.585580 -0.028303 11.00000 0.12583 0.12413 = 0.07489 -0.03112 -0.04014 0.02858 AFIX 43 H30 2 -0.268464 0.565031 -0.057706 11.00000 -1.20000 AFIX 0 C31 1 -0.250436 0.588548 0.023774 11.00000 0.08981 0.12317 = 0.08867 -0.03343 -0.02352 0.00662 AFIX 43 H31 2 -0.381745 0.570093 0.029666 11.00000 -1.20000 AFIX 0 C32 1 -0.122489 0.619111 0.067479 11.00000 0.07351 0.09459 = 0.06477 -0.02050 -0.00796 0.00965 AFIX 43 H32 2 -0.169188 0.622315 0.102611 11.00000 -1.20000 AFIX 0 HKLF 4 REM liuxh0307 in P2(1)/c REM R1 = 0.0667 for 3293 Fo > 4sig(Fo) and 0.1122 for all 5764 data REM 326 parameters refined using 0 restraints END WGHT 0.0518 0.6618 REM Instructions for potential hydrogen bonds HTAB C1 O1 EQIV $1 x-1, y, z HTAB C1 O2_$1 REM Highest difference peak 0.155, deepest hole -0.172, 1-sigma level 0.035 Q1 1 0.7314 0.6319 0.5124 11.00000 0.05 0.13 Q2 1 -0.1647 0.9445 0.0785 11.00000 0.05 0.13 Q3 1 0.4662 0.6750 0.5415 11.00000 0.05 0.12 Q4 1 0.0357 0.6182 0.1474 11.00000 0.05 0.12 Q5 1 0.5914 0.4741 0.1511 11.00000 0.05 0.12 Q6 1 0.2676 0.6998 0.0057 11.00000 0.05 0.12 Q7 1 0.4943 0.6467 0.3484 11.00000 0.05 0.12 Q8 1 0.6234 0.7411 0.5236 11.00000 0.05 0.12 Q9 1 0.4848 0.5615 0.2788 11.00000 0.05 0.11 Q10 1 0.5970 0.6430 0.1783 11.00000 0.05 0.11 Q11 1 0.5915 0.7995 0.1884 11.00000 0.05 0.11 Q12 1 0.5223 0.6186 0.1102 11.00000 0.05 0.11 Q13 1 0.0074 0.5861 0.0591 11.00000 0.05 0.11 Q14 1 -0.1314 0.8589 0.1811 11.00000 0.05 0.11 Q15 1 0.4364 0.3868 0.1609 11.00000 0.05 0.11 Q16 1 0.5874 0.9976 0.1125 11.00000 0.05 0.11 Q17 1 -0.0348 0.8013 0.2029 11.00000 0.05 0.11 Q18 1 -0.0452 0.7219 0.1677 11.00000 0.05 0.11 Q19 1 0.7486 0.8470 0.2093 11.00000 0.05 0.11 Q20 1 0.2269 0.5026 0.2170 11.00000 0.05 0.11 ; _shelx_res_checksum 35399 _olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)' _olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn O1 O 0.1282(2) 0.68600(10) 0.15336(6) 0.0490(4) Uani 1 1 d . O2 O 0.6514(3) 0.73053(13) 0.17341(8) 0.0759(6) Uani 1 1 d . N1 N 0.2060(3) 0.67336(13) 0.28703(8) 0.0569(5) Uani 1 1 d . N2 N 0.4059(3) 0.68851(14) 0.10373(8) 0.0621(6) Uani 1 1 d . C1 C -0.0063(4) 0.6461(2) 0.27662(12) 0.0782(9) Uani 1 1 d . H1A H -0.0656 0.6702 0.2423 0.094 Uiso 1 1 calc R H1B H -0.0850 0.6652 0.3063 0.094 Uiso 1 1 calc R C2 C -0.0222(5) 0.5557(2) 0.27278(14) 0.0930(11) Uani 1 1 d . H2A H -0.1605 0.5409 0.2583 0.112 Uiso 1 1 calc R H2B H 0.0021 0.5323 0.3095 0.112 Uiso 1 1 calc R C3 C 0.1301(5) 0.5202(2) 0.23592(12) 0.0801(9) Uani 1 1 d . C4 C 0.1074(8) 0.4409(3) 0.21567(17) 0.1226(16) Uani 1 1 d . H4 H -0.0084 0.4109 0.2231 0.147 Uiso 1 1 calc R C5 C 0.2504(10) 0.4054(3) 0.18506(19) 0.133(2) Uani 1 1 d . H5 H 0.2308 0.3521 0.1721 0.160 Uiso 1 1 calc R C6 C 0.4219(8) 0.4480(3) 0.17338(15) 0.1128(15) Uani 1 1 d . H6 H 0.5203 0.4236 0.1531 0.135 Uiso 1 1 calc R C7 C 0.4483(5) 0.5287(2) 0.19217(11) 0.0817(9) Uani 1 1 d . H7 H 0.5640 0.5583 0.1841 0.098 Uiso 1 1 calc R C8 C 0.3019(4) 0.56488(16) 0.22298(10) 0.0623(7) Uani 1 1 d . C9 C 0.3304(3) 0.65283(15) 0.24179(9) 0.0508(6) Uani 1 1 d . H9 H 0.4747 0.6586 0.2562 0.061 Uiso 1 1 calc R C10 C 0.2995(4) 0.67505(16) 0.34168(9) 0.0542(6) Uani 1 1 d . C11 C 0.1980(4) 0.64970(19) 0.38679(11) 0.0710(8) Uani 1 1 d . H11 H 0.0637 0.6302 0.3814 0.085 Uiso 1 1 calc R C12 C 0.2962(5) 0.6533(2) 0.43993(11) 0.0797(9) Uani 1 1 d . H12 H 0.2244 0.6364 0.4695 0.096 Uiso 1 1 calc R C13 C 0.4942(5) 0.68069(18) 0.45069(11) 0.0720(8) Uani 1 1 d . C14 C 0.5916(4) 0.70748(18) 0.40594(11) 0.0709(8) Uani 1 1 d . H14 H 0.7251 0.7276 0.4117 0.085 Uiso 1 1 calc R C15 C 0.4970(4) 0.70536(17) 0.35251(10) 0.0622(7) Uani 1 1 d . H15 H 0.5676 0.7247 0.3234 0.075 Uiso 1 1 calc R C16 C 0.6022(6) 0.6806(2) 0.50861(12) 0.1073(13) Uani 1 1 d . H16A H 0.7446 0.6946 0.5068 0.161 Uiso 1 1 calc GR H16B H 0.5923 0.6271 0.5246 0.161 Uiso 1 1 calc GR H16C H 0.5383 0.7200 0.5310 0.161 Uiso 1 1 calc GR C17 C 0.2948(3) 0.71370(14) 0.19255(9) 0.0479(5) Uani 1 1 d . C18 C 0.2472(4) 0.80047(15) 0.21108(10) 0.0615(7) Uani 1 1 d . H18A H 0.1165 0.7997 0.2274 0.074 Uiso 1 1 calc R H18B H 0.3521 0.8168 0.2398 0.074 Uiso 1 1 calc R C19 C 0.2365(4) 0.86415(15) 0.16611(10) 0.0564(6) Uani 1 1 d . C20 C 0.4013(4) 0.91550(18) 0.15959(12) 0.0729(8) Uani 1 1 d . H20 H 0.5210 0.9099 0.1830 0.087 Uiso 1 1 calc R C21 C 0.3917(6) 0.97484(19) 0.11909(15) 0.0877(10) Uani 1 1 d . H21 H 0.5034 1.0093 0.1156 0.105 Uiso 1 1 calc R C22 C 0.2173(6) 0.9829(2) 0.08411(13) 0.0920(10) Uani 1 1 d . H22 H 0.2108 1.0223 0.0563 0.110 Uiso 1 1 calc R C23 C 0.0526(6) 0.93297(19) 0.08991(13) 0.0854(10) Uani 1 1 d . H23 H -0.0662 0.9390 0.0662 0.102 Uiso 1 1 calc R C24 C 0.0603(4) 0.87356(17) 0.13061(12) 0.0696(8) Uani 1 1 d . H24 H -0.0529 0.8399 0.1342 0.084 Uiso 1 1 calc R C25 C 0.4755(4) 0.71308(16) 0.15704(10) 0.0573(6) Uani 1 1 d . C26 C 0.2115(4) 0.67397(15) 0.10536(9) 0.0517(6) Uani 1 1 d . C27 C 0.0727(4) 0.64465(16) 0.05917(10) 0.0601(7) Uani 1 1 d . C28 C 0.1397(5) 0.6421(2) 0.00634(12) 0.0846(9) Uani 1 1 d . H28 H 0.2713 0.6600 0.0003 0.101 Uiso 1 1 calc R C29 C 0.0104(7) 0.6128(3) -0.03709(13) 0.1072(13) Uani 1 1 d . H29 H 0.0545 0.6114 -0.0726 0.129 Uiso 1 1 calc R C30 C -0.1828(7) 0.5856(3) -0.02830(16) 0.1111(14) Uani 1 1 d . H30 H -0.2685 0.5650 -0.0577 0.133 Uiso 1 1 calc R C31 C -0.2504(5) 0.5885(2) 0.02377(15) 0.1023(12) Uani 1 1 d . H31 H -0.3817 0.5701 0.0297 0.123 Uiso 1 1 calc R C32 C -0.1225(4) 0.61911(19) 0.06748(12) 0.0784(9) Uani 1 1 d . H32 H -0.1692 0.6223 0.1026 0.094 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 O1 0.0512(9) 0.0591(10) 0.0363(8) -0.0004(7) 0.0015(6) 0.0041(8) O2 0.0532(11) 0.1056(17) 0.0691(12) 0.0007(11) 0.0062(9) -0.0058(10) N1 0.0465(11) 0.0845(15) 0.0400(10) 0.0046(10) 0.0060(8) 0.0053(10) N2 0.0618(13) 0.0826(16) 0.0431(11) 0.0015(10) 0.0114(9) 0.0059(12) C1 0.0517(15) 0.123(3) 0.0593(17) 0.0223(17) 0.0030(12) 0.0013(17) C2 0.081(2) 0.124(3) 0.072(2) 0.021(2) -0.0046(16) -0.034(2) C3 0.110(2) 0.068(2) 0.0573(17) 0.0160(15) -0.0206(16) -0.0158(18) C4 0.201(5) 0.078(3) 0.082(3) 0.018(2) -0.034(3) -0.039(3) C5 0.248(7) 0.064(3) 0.080(3) 0.004(2) -0.037(4) 0.008(3) C6 0.184(4) 0.081(3) 0.067(2) -0.004(2) -0.021(3) 0.052(3) C7 0.110(2) 0.078(2) 0.0532(16) -0.0031(15) -0.0111(15) 0.0320(19) C8 0.0818(18) 0.0590(17) 0.0432(13) 0.0082(12) -0.0112(12) 0.0121(15) C9 0.0481(13) 0.0641(16) 0.0398(12) 0.0003(11) 0.0016(9) 0.0062(11) C10 0.0563(14) 0.0633(16) 0.0434(13) 0.0029(11) 0.0061(10) 0.0101(12) C11 0.0710(17) 0.094(2) 0.0501(15) 0.0044(14) 0.0165(13) 0.0009(16) C12 0.104(2) 0.095(2) 0.0430(15) 0.0056(14) 0.0199(15) 0.0139(19) C13 0.100(2) 0.0725(19) 0.0423(14) -0.0065(13) 0.0000(14) 0.0182(17) C14 0.0777(18) 0.079(2) 0.0548(16) -0.0109(14) -0.0040(13) 0.0001(15) C15 0.0681(17) 0.0739(18) 0.0443(14) -0.0025(12) 0.0037(11) -0.0041(14) C16 0.152(3) 0.120(3) 0.0453(17) -0.0124(18) -0.0155(18) 0.033(2) C17 0.0503(13) 0.0548(14) 0.0379(11) -0.0006(10) 0.0002(9) 0.0016(11) C18 0.0729(17) 0.0604(16) 0.0510(14) -0.0042(12) 0.0046(12) 0.0042(14) C19 0.0709(16) 0.0484(14) 0.0493(14) -0.0051(11) 0.0029(12) -0.0001(13) C20 0.0744(18) 0.0654(19) 0.077(2) -0.0057(15) -0.0010(14) -0.0053(15) C21 0.108(3) 0.062(2) 0.095(2) 0.0001(18) 0.019(2) -0.0139(19) C22 0.143(3) 0.065(2) 0.067(2) 0.0100(16) 0.005(2) -0.003(2) C23 0.117(3) 0.065(2) 0.069(2) -0.0023(16) -0.0232(18) 0.0068(19) C24 0.0801(19) 0.0580(17) 0.0685(18) -0.0032(14) -0.0064(14) -0.0026(14) C25 0.0565(15) 0.0675(17) 0.0484(14) 0.0060(12) 0.0070(11) 0.0034(13) C26 0.0597(15) 0.0559(15) 0.0396(12) 0.0036(10) 0.0045(10) 0.0126(12) C27 0.0716(17) 0.0632(16) 0.0439(13) -0.0070(12) -0.0056(11) 0.0155(14) C28 0.101(2) 0.103(2) 0.0487(16) -0.0061(16) 0.0008(15) 0.0166(19) C29 0.136(3) 0.137(4) 0.0451(17) -0.0162(19) -0.0124(19) 0.029(3) C30 0.126(3) 0.124(3) 0.075(2) -0.031(2) -0.040(2) 0.029(3) C31 0.090(2) 0.123(3) 0.089(3) -0.033(2) -0.0235(19) 0.007(2) C32 0.0735(19) 0.095(2) 0.0648(18) -0.0205(16) -0.0080(14) 0.0097(17) 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 C26 O1 C17 106.12(17) C1 N1 C9 112.4(2) C10 N1 C1 119.8(2) C10 N1 C9 119.18(18) C26 N2 C25 105.5(2) N1 C1 H1A 109.2 N1 C1 H1B 109.2 N1 C1 C2 112.1(2) H1A C1 H1B 107.9 C2 C1 H1A 109.2 C2 C1 H1B 109.2 C1 C2 H2A 109.2 C1 C2 H2B 109.2 C1 C2 C3 112.0(3) H2A C2 H2B 107.9 C3 C2 H2A 109.2 C3 C2 H2B 109.2 C4 C3 C2 120.9(4) C4 C3 C8 118.1(4) C8 C3 C2 121.0(3) C3 C4 H4 119.0 C5 C4 C3 121.9(5) C5 C4 H4 119.0 C4 C5 H5 119.8 C6 C5 C4 120.3(4) C6 C5 H5 119.8 C5 C6 H6 120.3 C5 C6 C7 119.4(4) C7 C6 H6 120.3 C6 C7 H7 119.9 C8 C7 C6 120.2(4) C8 C7 H7 119.9 C3 C8 C9 120.6(3) C7 C8 C3 120.0(3) C7 C8 C9 119.5(3) N1 C9 C8 112.5(2) N1 C9 H9 106.8 N1 C9 C17 111.98(19) C8 C9 H9 106.8 C8 C9 C17 111.62(18) C17 C9 H9 106.8 C11 C10 N1 122.5(2) C15 C10 N1 120.4(2) C15 C10 C11 117.1(2) C10 C11 H11 119.9 C10 C11 C12 120.3(3) C12 C11 H11 119.9 C11 C12 H12 118.6 C13 C12 C11 122.8(3) C13 C12 H12 118.6 C12 C13 C14 116.4(2) C12 C13 C16 122.1(3) C14 C13 C16 121.4(3) C13 C14 H14 119.0 C13 C14 C15 122.0(3) C15 C14 H14 119.0 C10 C15 C14 121.3(3) C10 C15 H15 119.4 C14 C15 H15 119.4 C13 C16 H16A 109.5 C13 C16 H16B 109.5 C13 C16 H16C 109.5 H16A C16 H16B 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 O1 C17 C9 110.94(18) O1 C17 C18 108.78(18) O1 C17 C25 101.57(17) C18 C17 C9 112.83(19) C25 C17 C9 111.02(19) C25 C17 C18 111.1(2) C17 C18 H18A 108.5 C17 C18 H18B 108.5 H18A C18 H18B 107.5 C19 C18 C17 115.2(2) C19 C18 H18A 108.5 C19 C18 H18B 108.5 C20 C19 C18 120.9(2) C20 C19 C24 118.3(3) C24 C19 C18 120.8(2) C19 C20 H20 119.4 C21 C20 C19 121.3(3) C21 C20 H20 119.4 C20 C21 H21 120.2 C22 C21 C20 119.7(3) C22 C21 H21 120.2 C21 C22 H22 120.0 C23 C22 C21 120.0(3) C23 C22 H22 120.0 C22 C23 H23 119.6 C22 C23 C24 120.8(3) C24 C23 H23 119.6 C19 C24 H24 120.0 C23 C24 C19 120.0(3) C23 C24 H24 120.0 O2 C25 N2 126.5(2) O2 C25 C17 124.8(2) N2 C25 C17 108.7(2) O1 C26 C27 116.3(2) N2 C26 O1 118.1(2) N2 C26 C27 125.6(2) C28 C27 C26 119.6(3) C32 C27 C26 120.7(2) C32 C27 C28 119.7(3) C27 C28 H28 120.2 C29 C28 C27 119.7(3) C29 C28 H28 120.2 C28 C29 H29 119.8 C30 C29 C28 120.3(3) C30 C29 H29 119.8 C29 C30 H30 119.9 C29 C30 C31 120.2(3) C31 C30 H30 119.9 C30 C31 H31 120.1 C30 C31 C32 119.8(4) C32 C31 H31 120.1 C27 C32 C31 120.2(3) C27 C32 H32 119.9 C31 C32 H32 119.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C17 1.453(2) O1 C26 1.340(3) O2 C25 1.215(3) N1 C1 1.455(3) N1 C9 1.457(3) N1 C10 1.411(3) N2 C25 1.392(3) N2 C26 1.293(3) C1 H1A 0.9700 C1 H1B 0.9700 C1 C2 1.481(4) C2 H2A 0.9700 C2 H2B 0.9700 C2 C3 1.507(5) C3 C4 1.388(5) C3 C8 1.395(4) C4 H4 0.9300 C4 C5 1.368(6) C5 H5 0.9300 C5 C6 1.366(6) C6 H6 0.9300 C6 C7 1.400(5) C7 H7 0.9300 C7 C8 1.393(4) C8 C9 1.513(3) C9 H9 0.9800 C9 C17 1.555(3) C10 C11 1.389(3) C10 C15 1.383(3) C11 H11 0.9300 C11 C12 1.390(4) C12 H12 0.9300 C12 C13 1.370(4) C13 C14 1.374(4) C13 C16 1.516(4) C14 H14 0.9300 C14 C15 1.387(3) C15 H15 0.9300 C16 H16A 0.9600 C16 H16B 0.9600 C16 H16C 0.9600 C17 C18 1.526(3) C17 C25 1.517(3) C18 H18A 0.9700 C18 H18B 0.9700 C18 C19 1.504(3) C19 C20 1.383(4) C19 C24 1.384(3) C20 H20 0.9300 C20 C21 1.377(4) C21 H21 0.9300 C21 C22 1.365(4) C22 H22 0.9300 C22 C23 1.364(4) C23 H23 0.9300 C23 C24 1.381(4) C24 H24 0.9300 C26 C27 1.459(3) C27 C28 1.389(4) C27 C32 1.370(4) C28 H28 0.9300 C28 C29 1.377(4) C29 H29 0.9300 C29 C30 1.369(5) C30 H30 0.9300 C30 C31 1.373(5) C31 H31 0.9300 C31 C32 1.384(4) C32 H32 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 O1 C17 C18 C19 -63.5(3) O1 C17 C25 O2 -178.3(2) O1 C17 C25 N2 1.0(2) O1 C26 C27 C28 170.7(2) O1 C26 C27 C32 -9.8(4) N1 C1 C2 C3 -47.1(3) N1 C9 C17 O1 -89.8(2) N1 C9 C17 C18 32.5(3) N1 C9 C17 C25 158.05(19) N1 C10 C11 C12 -179.4(3) N1 C10 C15 C14 -179.9(2) N2 C26 C27 C28 -9.8(4) N2 C26 C27 C32 169.7(3) C1 N1 C9 C8 -47.3(3) C1 N1 C9 C17 79.4(3) C1 N1 C10 C11 1.5(4) C1 N1 C10 C15 -176.2(3) C1 C2 C3 C4 -163.7(3) C1 C2 C3 C8 18.9(4) C2 C3 C4 C5 -175.8(3) C2 C3 C8 C7 175.3(2) C2 C3 C8 C9 -5.1(4) C3 C4 C5 C6 -0.1(6) C3 C8 C9 N1 18.8(3) C3 C8 C9 C17 -108.1(2) C4 C3 C8 C7 -2.2(4) C4 C3 C8 C9 177.4(3) C4 C5 C6 C7 -1.1(6) C5 C6 C7 C8 0.7(5) C6 C7 C8 C3 1.0(4) C6 C7 C8 C9 -178.6(2) C7 C8 C9 N1 -161.7(2) C7 C8 C9 C17 71.4(3) C8 C3 C4 C5 1.8(5) C8 C9 C17 O1 37.4(3) C8 C9 C17 C18 159.7(2) C8 C9 C17 C25 -74.8(3) C9 N1 C1 C2 63.7(3) C9 N1 C10 C11 -143.9(3) C9 N1 C10 C15 38.4(3) C9 C17 C18 C19 173.0(2) C9 C17 C25 O2 -60.3(3) C9 C17 C25 N2 119.0(2) C10 N1 C1 C2 -83.9(3) C10 N1 C9 C8 100.5(3) C10 N1 C9 C17 -132.8(2) C10 C11 C12 C13 -0.5(5) C11 C10 C15 C14 2.3(4) C11 C12 C13 C14 2.0(5) C11 C12 C13 C16 -177.2(3) C12 C13 C14 C15 -1.4(4) C13 C14 C15 C10 -0.8(4) C15 C10 C11 C12 -1.6(4) C16 C13 C14 C15 177.8(3) C17 O1 C26 N2 -0.3(3) C17 O1 C26 C27 179.3(2) C17 C18 C19 C20 -99.7(3) C17 C18 C19 C24 81.1(3) C18 C17 C25 O2 66.2(3) C18 C17 C25 N2 -114.5(2) C18 C19 C20 C21 -179.0(3) C18 C19 C24 C23 179.3(3) C19 C20 C21 C22 -0.8(5) C20 C19 C24 C23 0.1(4) C20 C21 C22 C23 0.9(5) C21 C22 C23 C24 -0.6(5) C22 C23 C24 C19 0.0(5) C24 C19 C20 C21 0.2(4) C25 N2 C26 O1 0.9(3) C25 N2 C26 C27 -178.6(2) C25 C17 C18 C19 47.5(3) C26 O1 C17 C9 -118.5(2) C26 O1 C17 C18 116.8(2) C26 O1 C17 C25 -0.5(2) C26 N2 C25 O2 178.1(3) C26 N2 C25 C17 -1.2(3) C26 C27 C28 C29 178.6(3) C26 C27 C32 C31 -177.6(3) C27 C28 C29 C30 -0.6(6) C28 C27 C32 C31 1.9(5) C28 C29 C30 C31 1.1(6) C29 C30 C31 C32 0.0(6) C30 C31 C32 C27 -1.4(5) C32 C27 C28 C29 -0.9(5)