#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/81/1518141.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_1518141 loop_ _publ_author_name 'Brachet, E.' 'Ghosh, T.' 'Ghosh, I.' 'K\"onig, B.' _publ_section_title ; Visible light C--H amidation of heteroarenes with benzoyl azides ; _journal_issue 2 _journal_name_full 'Chem. Sci.' _journal_page_first 987 _journal_paper_doi 10.1039/C4SC02365J _journal_volume 6 _journal_year 2015 _chemical_formula_moiety 'C13 H14 N2 O2' _chemical_formula_sum 'C13 H14 N2 O2' _chemical_formula_weight 230.26 _chemical_name_systematic 2-(4-Chlorophenyl)-4-methyl-4-phenyl-4,5-dihydrooxazole _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 _atom_sites_solution_secondary difmap _audit_creation_date 2014-07-02 _audit_creation_method ; Olex2 1.2 (compiled 2014.06.23 svn.r2946 for OlexSys, GUI svn.r4855) ; _cell_angle_alpha 90.00 _cell_angle_beta 103.161(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 11.6434(3) _cell_length_b 10.03245(18) _cell_length_c 20.8570(4) _cell_measurement_reflns_used 5594 _cell_measurement_temperature 123.01(10) _cell_measurement_theta_max 63.2750 _cell_measurement_theta_min 3.8740 _cell_volume 2372.35(9) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _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-97 (Sheldrick, 1990)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 123.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2548 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.967 _diffrn_measured_fraction_theta_max 0.967 _diffrn_measurement_details ; 1 omega -124.00 -79.00 0.5000 4.5000 omega____ theta____ kappa____ phi______ frames - -41.6587 -99.0000 -60.0000 90 2 omega -123.00 -79.00 0.5000 4.5000 omega____ theta____ kappa____ phi______ frames - -41.6587 -99.0000 90.0000 88 3 omega -124.00 -79.00 0.5000 4.5000 omega____ theta____ kappa____ phi______ frames - -41.6587 -99.0000 -150.0000 90 4 omega -69.00 -6.00 0.5000 40.0000 omega____ theta____ kappa____ phi______ frames - -83.0000 30.0000 -90.0000 126 5 omega 64.00 153.00 0.5000 40.0000 omega____ theta____ kappa____ phi______ frames - 86.4674 45.0000 -180.0000 178 6 omega 64.00 145.00 0.5000 40.0000 omega____ theta____ kappa____ phi______ frames - 86.4674 45.0000 90.0000 162 7 omega 2.00 105.00 0.5000 40.0000 omega____ theta____ kappa____ phi______ frames - 86.4674 -94.0000 -30.0000 206 8 omega -120.00 -8.00 0.5000 4.5000 omega____ theta____ kappa____ phi______ frames - -41.6587 -77.0000 -150.0000 224 9 omega -117.00 -10.00 0.5000 4.5000 omega____ theta____ kappa____ phi______ frames - -41.6587 -67.0000 -37.0000 214 10 omega 12.00 42.00 0.5000 40.0000 omega____ theta____ kappa____ phi______ frames - 86.4674 -45.0000 90.0000 60 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Single source at offset, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0540875000 _diffrn_orient_matrix_UB_12 0.1019833000 _diffrn_orient_matrix_UB_13 0.0398623000 _diffrn_orient_matrix_UB_21 -0.0741198000 _diffrn_orient_matrix_UB_22 0.0587027000 _diffrn_orient_matrix_UB_23 -0.0645227000 _diffrn_orient_matrix_UB_31 -0.1002089000 _diffrn_orient_matrix_UB_32 -0.0985891000 _diffrn_orient_matrix_UB_33 0.0027279000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_unetI/netI 0.0246 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 9809 _diffrn_reflns_theta_full 63.48 _diffrn_reflns_theta_max 63.48 _diffrn_reflns_theta_min 3.90 _diffrn_source 'sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.719 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_correction_T_min 0.991 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_crystal_size_max 0.1345 _exptl_crystal_size_mid 0.1066 _exptl_crystal_size_min 0.0361 _refine_diff_density_max 0.201 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.040 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 367 _refine_ls_number_reflns 3758 _refine_ls_number_restraints 190 _refine_ls_restrained_S_all 1.070 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0366 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.6172P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0975 _refine_ls_wR_factor_ref 0.1027 _reflns_number_gt 3356 _reflns_number_total 3758 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c4sc02365j2.cif _cod_data_source_block n071 _cod_depositor_comments 'Adding full bibliography for 1518141.cif.' _cod_original_cell_volume 2372.35(8) _cod_database_code 1518141 #BEGIN Tags that were not found in dictionaries: _chemical_oxdiff_formula 'C13 H14 N2 O2' _reflns_odcompleteness_completeness 95.22 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 64.00 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C22-N4 \\sim C22A-N4A with sigma of 0.001 C22-C23 \\sim C22A-C23A with sigma of 0.001 N4A-C25A \\sim N4-C25 with sigma of 0.001 C24A-C25A \\sim C25-C24 with sigma of 0.001 3. Uiso/Uaniso restraints and constraints N4 \\sim C25 \\sim C26 \\sim C23 \\sim C22 \\sim C24 \\sim N4A \\sim C25A \\sim C24A \\sim C23A \\sim C22A \\sim C26A: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.005 4. Others Sof(H3B)=Sof(N4A)=Sof(C25A)=Sof(H25A)=Sof(C24A)=Sof(H24A)=Sof(C23A)=Sof(H23A)= Sof(C22A)=Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(1) Sof(H3A)=Sof(N4)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)= Sof(C23)=Sof(H23)=Sof(C22)=Sof(C24)=Sof(H24)=FVAR(1) 5.a Aromatic/amide H refined with riding coordinates: N1(H1), N3(H3A), N3(H3B), C10(H10), C19(H19), C15(H15), C11(H11), C18(H18), C2(H2), C16(H16), C25(H25), C6(H6), C12(H12), C5(H5), C23(H23), C3(H3), C24(H24), C25A(H25A), C24A(H24A), C23A(H23A) 5.b Idealised Me refined as rotating group: C20(H20A,H20B,H20C), C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C26(H26A,H26B, H26C), C26A(H26D,H26E,H26F) ; _olex2_submission_special_instructions 'No special instructions were received' #END Tags that were not found in dictionaries loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 '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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn O3 O 0.85364(10) 0.00048(11) 0.22196(5) 0.0404(3) Uani 1 d . . . O1 O 0.53025(10) 0.50345(11) 0.29770(5) 0.0396(3) Uani 1 d . . . O4 O 0.75084(10) 0.23978(10) 0.48319(5) 0.0376(3) Uani 1 d . . . O2 O 0.30639(11) 0.25278(10) 0.51790(5) 0.0413(3) Uani 1 d . . . N1 N 0.25305(11) 0.46420(11) 0.53170(6) 0.0290(3) Uani 1 d . . . H1 H 0.2635 0.5471 0.5242 0.035 Uiso 1 calc . . R N3 N 0.71851(12) 0.02452(12) 0.50363(6) 0.0332(3) Uani 1 d . . . H3A H 0.7207 -0.0564 0.4903 0.040 Uiso 0.826(2) calc A 1 R H3B H 0.6795 -0.0445 0.4865 0.040 Uiso 0.174(2) calc A 2 R N2 N 0.07242(11) 0.36688(12) 0.54828(6) 0.0327(3) Uani 1 d . . . N4 N 0.77433(16) 0.02577(16) 0.62105(8) 0.0378(4) Uani 0.826(2) d A 1 . C20 C 0.85345(17) -0.13321(18) 0.19885(8) 0.0445(4) Uani 1 d . . . H20A H 0.8815 -0.1347 0.1590 0.067 Uiso 1 calc . . GR H20B H 0.7746 -0.1681 0.1903 0.067 Uiso 1 calc . . GR H20C H 0.9041 -0.1869 0.2317 0.067 Uiso 1 calc . . GR C7 C 0.52688(17) 0.63705(19) 0.27350(9) 0.0496(5) Uani 1 d . . . H7A H 0.5703 0.6421 0.2396 0.074 Uiso 1 calc . . GR H7B H 0.5616 0.6960 0.3089 0.074 Uiso 1 calc . . GR H7C H 0.4465 0.6627 0.2558 0.074 Uiso 1 calc . . GR C10 C 0.18453(14) 0.45899(15) 0.63815(7) 0.0323(3) Uani 1 d . . . H10 H 0.2468 0.5010 0.6669 0.039 Uiso 1 calc . . R C19 C 0.81877(14) 0.15282(15) 0.29983(8) 0.0363(4) Uani 1 d . . . H19 H 0.8375 0.2207 0.2736 0.044 Uiso 1 calc . . R C14 C 0.81823(13) 0.02089(15) 0.27914(7) 0.0314(3) Uani 1 d . . . C15 C 0.78608(14) -0.07908(15) 0.31708(7) 0.0332(4) Uani 1 d . . . H15 H 0.7824 -0.1670 0.3027 0.040 Uiso 1 calc . . R C11 C 0.07911(15) 0.41307(15) 0.65317(8) 0.0371(4) Uani 1 d . . . H11 H 0.0586 0.4203 0.6936 0.045 Uiso 1 calc . . R C18 C 0.79161(13) 0.18298(15) 0.35896(7) 0.0328(3) Uani 1 d A . . H18 H 0.7926 0.2714 0.3724 0.039 Uiso 1 calc . . R C2 C 0.41291(14) 0.57591(16) 0.37389(8) 0.0361(4) Uani 1 d . . . H2 H 0.4051 0.6616 0.3565 0.043 Uiso 1 calc . . R C13 C 0.03216(15) 0.31688(17) 0.48156(8) 0.0418(4) Uani 1 d . . . H13A H 0.0460 0.3830 0.4509 0.063 Uiso 1 calc . . GR H13B H -0.0507 0.2977 0.4733 0.063 Uiso 1 calc . . GR H13C H 0.0745 0.2370 0.4764 0.063 Uiso 1 calc . . GR C16 C 0.75926(14) -0.04770(15) 0.37672(7) 0.0323(3) Uani 1 d A . . H16 H 0.7386 -0.1155 0.4023 0.039 Uiso 1 calc . . R C25 C 0.7228(3) 0.0398(3) 0.67357(11) 0.0445(7) Uani 0.826(2) d A 1 . H25 H 0.7610 0.0307 0.7176 0.053 Uiso 0.826(2) calc A 1 R C9 C 0.17763(13) 0.42994(13) 0.57328(7) 0.0281(3) Uani 1 d . . . C6 C 0.49030(14) 0.35395(16) 0.37579(7) 0.0359(4) Uani 1 d . . . H6 H 0.5348 0.2906 0.3596 0.043 Uiso 1 calc . . R C17 C 0.76267(12) 0.08329(14) 0.39904(7) 0.0268(3) Uani 1 d . . . C12 C 0.01272(15) 0.35609(15) 0.59745(8) 0.0385(4) Uani 1 d . . . H12 H -0.0608 0.3166 0.5936 0.046 Uiso 1 calc . . R C21 C 0.74283(12) 0.12280(14) 0.46478(7) 0.0274(3) Uani 1 d A . . C26 C 0.8959(2) -0.0073(3) 0.62487(15) 0.0560(7) Uani 0.826(2) d A 1 . H26A H 0.9433 0.0239 0.6659 0.084 Uiso 0.826(2) calc A 1 GR H26B H 0.9216 0.0344 0.5891 0.084 Uiso 0.826(2) calc A 1 GR H26C H 0.9039 -0.1022 0.6221 0.084 Uiso 0.826(2) calc A 1 GR C5 C 0.43724(14) 0.32162(15) 0.42642(7) 0.0348(4) Uani 1 d . . . H5 H 0.4459 0.2361 0.4441 0.042 Uiso 1 calc . . R C1 C 0.47726(13) 0.48127(15) 0.34887(7) 0.0325(3) Uani 1 d . . . C23 C 0.5850(3) 0.0709(4) 0.5823(2) 0.0424(8) Uani 0.826(2) d A 1 . H23 H 0.5124 0.0860 0.5536 0.051 Uiso 0.826(2) calc A 1 R C4 C 0.37073(13) 0.41550(14) 0.45160(7) 0.0295(3) Uani 1 d . . . C22 C 0.68971(17) 0.04621(17) 0.56473(8) 0.0282(4) Uani 0.826(2) d A 1 . C3 C 0.36021(14) 0.54275(15) 0.42491(7) 0.0333(3) Uani 1 d . . . H3 H 0.3171 0.6068 0.4415 0.040 Uiso 1 calc . . R C8 C 0.30972(13) 0.37137(14) 0.50314(7) 0.0295(3) Uani 1 d . . . C24 C 0.6072(2) 0.0692(2) 0.65076(10) 0.0431(5) Uani 0.826(2) d A 1 . H24 H 0.5526 0.0852 0.6762 0.052 Uiso 0.826(2) calc A 1 R N4A N 0.6732(8) 0.0636(8) 0.6099(4) 0.0400(11) Uani 0.174(2) d A 2 . C25A C 0.7213(10) 0.0731(18) 0.6762(4) 0.0425(14) Uani 0.174(2) d A 2 . H25A H 0.6806 0.0907 0.7088 0.051 Uiso 0.174(2) calc A 2 R C24A C 0.8388(9) 0.0523(10) 0.6855(5) 0.0453(13) Uani 0.174(2) d A 2 . H24A H 0.8926 0.0490 0.7259 0.054 Uiso 0.174(2) calc A 2 R C23A C 0.8658(12) 0.0365(13) 0.6238(6) 0.0432(16) Uani 0.174(2) d A 2 . H23A H 0.9406 0.0276 0.6156 0.052 Uiso 0.174(2) calc A 2 R C22A C 0.7606(8) 0.0365(10) 0.5779(5) 0.0391(13) Uani 0.174(2) d A 2 . C26A C 0.5620(19) 0.090(3) 0.5767(12) 0.0398(16) Uani 0.174(2) d A 2 . H26D H 0.5086 0.0730 0.6047 0.060 Uiso 0.174(2) calc A 2 GR H26E H 0.5421 0.0329 0.5387 0.060 Uiso 0.174(2) calc A 2 GR H26F H 0.5561 0.1811 0.5630 0.060 Uiso 0.174(2) calc A 2 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 O3 0.0523(7) 0.0444(7) 0.0302(6) 0.0035(5) 0.0210(5) 0.0030(5) O1 0.0448(7) 0.0441(7) 0.0359(6) 0.0038(5) 0.0216(5) -0.0008(5) O4 0.0530(7) 0.0237(6) 0.0416(6) -0.0056(5) 0.0221(5) -0.0061(5) O2 0.0648(8) 0.0237(6) 0.0428(6) 0.0053(5) 0.0278(6) 0.0044(5) N1 0.0410(7) 0.0202(6) 0.0295(6) -0.0005(5) 0.0156(5) -0.0032(5) N3 0.0518(8) 0.0226(6) 0.0295(6) -0.0029(5) 0.0186(6) -0.0049(5) N2 0.0392(7) 0.0268(7) 0.0338(7) 0.0001(5) 0.0117(5) -0.0030(5) N4 0.0445(10) 0.0381(8) 0.0293(9) -0.0005(7) 0.0056(7) 0.0072(7) C20 0.0566(11) 0.0512(11) 0.0301(8) -0.0026(7) 0.0193(7) 0.0047(8) C7 0.0532(11) 0.0521(11) 0.0522(10) 0.0168(9) 0.0302(9) 0.0052(9) C10 0.0425(9) 0.0271(8) 0.0293(8) 0.0023(6) 0.0125(6) 0.0015(6) C19 0.0455(9) 0.0323(8) 0.0346(8) 0.0102(7) 0.0162(7) 0.0008(7) C14 0.0321(8) 0.0394(9) 0.0248(7) 0.0038(6) 0.0109(6) 0.0032(6) C15 0.0445(9) 0.0271(8) 0.0311(8) -0.0008(6) 0.0148(7) 0.0000(6) C11 0.0490(10) 0.0326(8) 0.0355(8) 0.0081(7) 0.0217(7) 0.0066(7) C18 0.0397(9) 0.0252(8) 0.0354(8) 0.0034(6) 0.0125(7) 0.0002(6) C2 0.0469(9) 0.0292(8) 0.0365(8) 0.0039(6) 0.0184(7) -0.0012(7) C13 0.0458(10) 0.0359(9) 0.0422(9) -0.0061(7) 0.0067(7) -0.0045(7) C16 0.0436(9) 0.0267(8) 0.0307(8) 0.0026(6) 0.0170(6) -0.0029(6) C25 0.0709(13) 0.0393(17) 0.0247(9) 0.0009(9) 0.0137(9) 0.0096(11) C9 0.0360(8) 0.0197(7) 0.0308(7) 0.0021(6) 0.0122(6) -0.0006(6) C6 0.0419(9) 0.0352(9) 0.0335(8) -0.0030(7) 0.0147(7) 0.0048(7) C17 0.0267(7) 0.0265(7) 0.0285(7) 0.0018(6) 0.0092(6) -0.0004(6) C12 0.0410(9) 0.0305(8) 0.0498(10) 0.0086(7) 0.0226(8) -0.0002(7) C21 0.0262(7) 0.0260(8) 0.0312(7) -0.0014(6) 0.0089(6) -0.0015(6) C26 0.0499(15) 0.0652(18) 0.0476(12) -0.0047(13) -0.0002(11) 0.0124(11) C5 0.0468(9) 0.0287(8) 0.0316(8) 0.0015(6) 0.0143(7) 0.0032(7) C1 0.0340(8) 0.0387(9) 0.0273(7) -0.0007(6) 0.0118(6) -0.0053(6) C23 0.0512(19) 0.0401(17) 0.0367(13) 0.0023(11) 0.0117(13) 0.0109(12) C4 0.0367(8) 0.0280(8) 0.0250(7) -0.0019(6) 0.0093(6) -0.0017(6) C22 0.0398(11) 0.0227(8) 0.0238(9) 0.0000(7) 0.0109(8) 0.0005(8) C3 0.0442(9) 0.0258(8) 0.0345(8) -0.0004(6) 0.0182(7) -0.0001(6) C8 0.0390(8) 0.0238(8) 0.0270(7) 0.0009(6) 0.0102(6) -0.0011(6) C24 0.0641(12) 0.0384(10) 0.0347(10) 0.0026(8) 0.0275(9) 0.0082(9) N4A 0.0537(19) 0.0363(19) 0.0311(18) 0.0021(17) 0.0120(18) 0.0054(18) C25A 0.062(2) 0.039(3) 0.028(2) 0.000(2) 0.014(2) 0.006(2) C24A 0.057(2) 0.043(2) 0.033(2) -0.003(2) 0.007(2) 0.007(2) C23A 0.052(3) 0.041(3) 0.035(2) -0.002(3) 0.008(3) 0.010(3) C22A 0.048(2) 0.036(2) 0.032(2) 0.001(2) 0.008(2) 0.007(2) C26A 0.053(3) 0.036(3) 0.033(3) 0.000(3) 0.014(3) 0.007(3) 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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 0 13 0.0148 0.0003 0.0008 12.9986 0.5182 -0.8387 0.0353 0 0 -13 0.0213 -0.0003 -0.0008 -12.9986 -0.5182 0.8387 -0.0353 -7 1 2 0.0661 -7.0025 0.9986 2.0018 0.5604 0.4485 0.6087 1 -6 2 0.0355 1.0079 -5.9979 1.9929 -0.5868 -0.5554 0.4958 8 0 -2 0.0429 8.0015 0.0013 -2.0007 -0.5124 -0.4639 -0.8074 0 6 -2 0.0643 -0.0077 5.9981 -1.9930 0.5327 0.4813 -0.5960 -3 6 -1 0.0572 -3.0083 5.9976 -0.9928 0.7348 0.6391 -0.2926 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C14 O3 C20 117.37(12) C1 O1 C7 116.56(12) C9 N1 H1 118.8 C8 N1 H1 118.8 C8 N1 C9 122.45(12) H3A N3 H3B 32.7 C21 N3 H3A 118.0 C21 N3 H3B 120.3 C21 N3 C22 123.92(13) C21 N3 C22A 119.5(4) C22 N3 H3A 118.0 C22 N3 H3B 106.7 C22 N3 C22A 32.0(3) C22A N3 H3A 112.2 C22A N3 H3B 120.3 C9 N2 C13 126.07(13) C12 N2 C13 125.63(14) C12 N2 C9 108.29(13) C25 N4 C26 125.7(2) C22 N4 C25 108.08(19) C22 N4 C26 126.2(2) O3 C20 H20A 109.5 O3 C20 H20B 109.5 O3 C20 H20C 109.5 H20A C20 H20B 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 O1 C7 H7A 109.5 O1 C7 H7B 109.5 O1 C7 H7C 109.5 H7A C7 H7B 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 C11 C10 H10 126.5 C9 C10 H10 126.5 C9 C10 C11 106.96(14) C14 C19 H19 119.9 C18 C19 H19 119.9 C18 C19 C14 120.11(14) O3 C14 C19 115.67(13) O3 C14 C15 124.59(14) C15 C14 C19 119.72(13) C14 C15 H15 120.2 C14 C15 C16 119.68(14) C16 C15 H15 120.2 C10 C11 H11 126.3 C12 C11 C10 107.46(13) C12 C11 H11 126.3 C19 C18 H18 119.4 C19 C18 C17 121.12(14) C17 C18 H18 119.4 C1 C2 H2 120.1 C1 C2 C3 119.87(14) C3 C2 H2 120.1 N2 C13 H13A 109.5 N2 C13 H13B 109.5 N2 C13 H13C 109.5 H13A C13 H13B 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C15 C16 H16 119.3 C15 C16 C17 121.31(13) C17 C16 H16 119.3 N4 C25 H25 125.6 C24 C25 N4 108.8(2) C24 C25 H25 125.6 N2 C9 N1 120.39(13) C10 C9 N1 130.67(14) C10 C9 N2 108.68(13) C5 C6 H6 120.0 C5 C6 C1 119.94(14) C1 C6 H6 120.0 C18 C17 C21 117.97(13) C16 C17 C18 118.00(13) C16 C17 C21 123.96(12) N2 C12 H12 125.7 C11 C12 N2 108.60(14) C11 C12 H12 125.7 O4 C21 N3 121.43(13) O4 C21 C17 121.47(13) N3 C21 C17 117.08(12) C6 C5 H5 119.6 C6 C5 C4 120.89(14) C4 C5 H5 119.6 O1 C1 C2 124.22(14) O1 C1 C6 115.96(13) C2 C1 C6 119.82(13) C22 C23 H23 126.2 C22 C23 C24 107.6(3) C24 C23 H23 126.2 C5 C4 C8 117.98(13) C3 C4 C5 118.43(13) C3 C4 C8 123.51(13) N4 C22 N3 118.80(16) N4 C22 C23 108.0(2) C23 C22 N3 132.7(2) C2 C3 C4 121.03(14) C2 C3 H3 119.5 C4 C3 H3 119.5 O2 C8 N1 120.51(13) O2 C8 C4 121.10(13) N1 C8 C4 118.33(12) C25 C24 C23 107.5(2) C25 C24 H24 126.3 C23 C24 H24 126.3 C22A N4A C25A 109.2(10) C26A N4A C25A 129.0(14) C26A N4A C22A 121.5(14) N4A C25A H25A 126.2 C24A C25A N4A 107.5(9) C24A C25A H25A 126.2 C25A C24A H24A 125.8 C25A C24A C23A 108.5(9) C23A C24A H24A 125.8 C24A C23A H23A 126.6 C22A C23A C24A 106.9(12) C22A C23A H23A 126.6 N4A C22A N3 114.3(7) N4A C22A C23A 107.7(11) C23A C22A N3 137.8(8) N4A C26A H26D 109.5 N4A C26A H26E 109.5 N4A C26A H26F 109.5 H26D C26A H26E 109.5 H26D C26A H26F 109.5 H26E C26A H26F 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O3 C20 1.425(2) O3 C14 1.3632(17) O1 C7 1.430(2) O1 C1 1.3672(17) O4 C21 1.2317(17) O2 C8 1.2317(17) N1 H1 0.8600 N1 C9 1.4100(18) N1 C8 1.3553(18) N3 H3A 0.8600 N3 H3B 0.8600 N3 C21 1.3466(18) N3 C22 1.407(2) N3 C22A 1.519(10) N2 C13 1.453(2) N2 C9 1.372(2) N2 C12 1.368(2) N4 C25 1.371(3) N4 C26 1.438(3) N4 C22 1.366(2) C20 H20A 0.9600 C20 H20B 0.9600 C20 H20C 0.9600 C7 H7A 0.9600 C7 H7B 0.9600 C7 H7C 0.9600 C10 H10 0.9300 C10 C11 1.411(2) C10 C9 1.368(2) C19 H19 0.9300 C19 C14 1.392(2) C19 C18 1.375(2) C14 C15 1.381(2) C15 H15 0.9300 C15 C16 1.386(2) C11 H11 0.9300 C11 C12 1.366(2) C18 H18 0.9300 C18 C17 1.393(2) C2 H2 0.9300 C2 C1 1.383(2) C2 C3 1.385(2) C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 C16 H16 0.9300 C16 C17 1.392(2) C25 H25 0.9300 C25 C24 1.353(4) C6 H6 0.9300 C6 C5 1.378(2) C6 C1 1.390(2) C17 C21 1.4948(19) C12 H12 0.9300 C26 H26A 0.9600 C26 H26B 0.9600 C26 H26C 0.9600 C5 H5 0.9300 C5 C4 1.396(2) C23 H23 0.9300 C23 C22 1.373(5) C23 C24 1.393(5) C4 C3 1.387(2) C4 C8 1.484(2) C3 H3 0.9300 C24 H24 0.9300 N4A C25A 1.371(3) N4A C22A 1.366(3) N4A C26A 1.35(2) C25A H25A 0.9300 C25A C24A 1.354(4) C24A H24A 0.9300 C24A C23A 1.400(17) C23A H23A 0.9300 C23A C22A 1.372(5) C26A H26D 0.9600 C26A H26E 0.9600 C26A H26F 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 O3 C14 C15 C16 175.58(14) N4 C25 C24 C23 1.2(3) C20 O3 C14 C19 -179.53(14) C20 O3 C14 C15 2.2(2) C7 O1 C1 C2 6.0(2) C7 O1 C1 C6 -174.42(15) C10 C11 C12 N2 -0.90(18) C19 C14 C15 C16 -2.6(2) C19 C18 C17 C16 -1.5(2) C19 C18 C17 C21 175.61(14) C14 C19 C18 C17 -0.3(2) C14 C15 C16 C17 0.8(2) C15 C16 C17 C18 1.3(2) C15 C16 C17 C21 -175.65(14) C11 C10 C9 N1 173.49(14) C11 C10 C9 N2 -0.56(17) C18 C19 C14 O3 -175.95(14) C18 C19 C14 C15 2.4(2) C18 C17 C21 O4 0.5(2) C18 C17 C21 N3 -178.02(13) C13 N2 C9 N1 6.7(2) C13 N2 C9 C10 -178.55(14) C13 N2 C12 C11 179.14(14) C16 C17 C21 O4 177.44(14) C16 C17 C21 N3 -1.1(2) C25 N4 C22 N3 -173.97(18) C25 N4 C22 C23 -1.0(3) C9 N1 C8 O2 -7.3(2) C9 N1 C8 C4 169.83(13) C9 N2 C12 C11 0.56(17) C9 C10 C11 C12 0.90(17) C6 C5 C4 C3 -0.7(2) C6 C5 C4 C8 176.11(14) C12 N2 C9 N1 -174.76(13) C12 N2 C9 C10 0.02(17) C21 N3 C22 N4 -101.84(19) C21 N3 C22 C23 87.2(4) C21 N3 C22A N4A 106.7(7) C21 N3 C22A C23A -67.8(15) C26 N4 C25 C24 -179.1(2) C26 N4 C22 N3 4.9(3) C26 N4 C22 C23 177.9(3) C5 C6 C1 O1 -178.31(14) C5 C6 C1 C2 1.2(2) C5 C4 C3 C2 0.9(2) C5 C4 C8 O2 -8.2(2) C5 C4 C8 N1 174.64(14) C1 C2 C3 C4 0.0(2) C1 C6 C5 C4 -0.4(2) C22 N3 C21 O4 6.1(2) C22 N3 C21 C17 -175.42(14) C22 N3 C22A N4A -1.0(4) C22 N3 C22A C23A -175.5(19) C22 N4 C25 C24 -0.2(3) C22 C23 C24 C25 -1.8(4) C3 C2 C1 O1 178.48(15) C3 C2 C1 C6 -1.0(2) C3 C4 C8 O2 168.37(15) C3 C4 C8 N1 -8.8(2) C8 N1 C9 N2 -67.93(19) C8 N1 C9 C10 118.61(18) C8 C4 C3 C2 -175.70(14) C24 C23 C22 N3 173.3(2) C24 C23 C22 N4 1.7(4) N4A C25A C24A C23A 3.2(17) C25A N4A C22A N3 -179.5(10) C25A N4A C22A C23A -3.4(14) C25A C24A C23A C22A -5.2(16) C24A C23A C22A N3 180.0(10) C24A C23A C22A N4A 5.2(13) C22A N3 C21 O4 -31.4(4) C22A N3 C21 C17 147.1(4) C22A N3 C22 N4 -9.3(7) C22A N3 C22 C23 179.7(9) C22A N4A C25A C24A 0.1(16) C26A N4A C25A C24A -172.8(17) C26A N4A C22A N3 -6.0(18) C26A N4A C22A C23A 170.2(16)