#------------------------------------------------------------------------------ #$Date: 2025-08-19 20:30:04 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301811 $ #$URL: svn://www.crystallography.net/cod/cif/4/00/07/4000705.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_4000705 loop_ _publ_author_name 'Massin, Julien' 'Dayoub, Wissam' 'Mulatier, Jean-Christophe' 'Aronica, Christophe' 'Bretonni\`ere, Yann' 'Andraud, Chantal' _publ_section_title ; Near-Infrared Solid-State Emitters Based on Isophorone: Synthesis, Crystal Structure and Spectroscopic Properties ; _journal_coden_ASTM CMATEX _journal_issue 3 _journal_name_full 'Chemistry of Materials' _journal_page_first 862 _journal_page_last 873 _journal_paper_doi 10.1021/cm102165r _journal_volume 23 _journal_year 2011 _chemical_absolute_configuration ad _chemical_formula_moiety 'C58 H62 N6' _chemical_formula_sum 'C29 H31 N3' _chemical_formula_weight 421.58 _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 09-06-18 _audit_creation_method CRYSTALS_ver_12.87 _cell_angle_alpha 90 _cell_angle_beta 91.896(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.552(5) _cell_length_b 7.519(5) _cell_length_c 38.551(5) _cell_measurement_reflns_used 0 _cell_measurement_temperature 293 _cell_measurement_theta_max 0 _cell_measurement_theta_min 0 _cell_volume 2478(2) _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _diffrn_ambient_temperature 293 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.841 _diffrn_measurement_device Unknown _diffrn_measurement_device_type Serial _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.067 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 15860 _diffrn_reflns_theta_full 25.256 _diffrn_reflns_theta_max 29.367 _diffrn_reflns_theta_min 2.639 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.130 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 904 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.17 _refine_diff_density_min -0.17 _refine_ls_abs_structure_details 'Flack (1983), 3897 Friedel-pairs' _refine_ls_abs_structure_Flack -2(5) _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.7826 _refine_ls_hydrogen_treatment none _refine_ls_matrix_type full _refine_ls_number_parameters 578 _refine_ls_number_reflns 6055 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1503 _refine_ls_R_factor_gt 0.0574 _refine_ls_shift/su_max 0.0006116 _refine_ls_shift/su_mean 1.5220608 _refine_ls_structure_factor_coef F _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 11.3 0.641 6.47 1.77 -2.33 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1263 _refine_ls_wR_factor_gt 0.0743 _refine_ls_wR_factor_ref 0.0743 _reflns_limit_h_max 10 _reflns_limit_h_min -11 _reflns_limit_k_max 9 _reflns_limit_k_min -10 _reflns_limit_l_max 48 _reflns_limit_l_min 0 _reflns_number_gt 6055 _reflns_number_total 10049 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _oxford_refine_ls_r_factor_ref 0.0574 _oxford_refine_ls_scale 2.198(5) _oxford_reflns_number_all 15771 _oxford_reflns_threshold_expression_ref I>2.0\s(I) _oxford_structure_analysis_title 'wd01 in P 21' _cod_data_source_file cm102165r_si_003.cif _cod_data_source_block JMenantiopur _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana Updated bibliographic information. Antanas Vaitkus, 2019-09-24 ; _cod_original_sg_symbol_H-M 'P 1 21 1 ' _cod_database_code 4000705 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn N1 N 0.3071(6) -0.2829(7) 0.08120(11) 0.0586 1.0000 Uani . N2 N 0.0782(6) 0.4110(7) 0.41806(13) 0.0600 1.0000 Uani . C3 C 0.3441(6) 0.0035(8) 0.17506(12) 0.0437 1.0000 Uani . C4 C 0.3987(6) -0.2588(8) 0.14132(13) 0.0519 1.0000 Uani . C5 C 0.0255(6) 0.1228(8) 0.32439(15) 0.0509 1.0000 Uani . C6 C -0.0511(6) -0.3343(8) 0.20047(13) 0.0495 1.0000 Uani . C7 C 0.5110(7) 0.0862(8) 0.29674(14) 0.0558 1.0000 Uani . C8 C 0.3220(6) -0.1880(8) 0.11110(14) 0.0485 1.0000 Uani . C9 C 0.4289(6) 0.1526(8) 0.26932(14) 0.0467 1.0000 Uani . C10 C 0.4054(7) -0.1652(8) 0.17193(13) 0.0506 1.0000 Uani . C11 C -0.1444(6) 0.0302(8) 0.20213(15) 0.0550 1.0000 Uani . C12 C -0.0667(6) -0.0333(8) 0.23109(15) 0.0504 1.0000 Uani . C13 C 0.5252(7) 0.1723(8) 0.32961(14) 0.0505 1.0000 Uani . C14 C 0.1192(7) 0.0604(8) 0.35210(15) 0.0578 1.0000 Uani . C15 C -0.2238(7) 0.0125(8) 0.14108(16) 0.0575 1.0000 Uani . C16 C 0.2628(6) -0.0158(8) 0.11406(14) 0.0545 1.0000 Uani . C17 C 0.3499(6) 0.1017(8) 0.20713(14) 0.0494 1.0000 Uani . C18 C 0.3460(6) 0.3256(8) 0.27263(14) 0.0568 1.0000 Uani . C19 C 0.6010(7) 0.0960(9) 0.35706(15) 0.0585 1.0000 Uani . C20 C 0.2720(6) 0.0737(8) 0.14512(14) 0.0557 1.0000 Uani . C21 C -0.1481(6) -0.0566(8) 0.16952(14) 0.0484 1.0000 Uani . C22 C 0.4507(7) 0.3490(8) 0.33371(12) 0.0526 1.0000 Uani . C23 C -0.0609(7) -0.2302(8) 0.16650(14) 0.0595 1.0000 Uani . C24 C 0.4222(6) 0.4530(7) 0.29964(13) 0.0491 1.0000 Uani . C25 C 0.4220(6) 0.0558(8) 0.23736(14) 0.0544 1.0000 Uani . C26 C 0.3442(7) -0.4746(9) 0.07942(13) 0.0608 1.0000 Uani . C27 C 0.0130(6) 0.0241(8) 0.29267(15) 0.0561 1.0000 Uani . C28 C 0.1355(7) 0.1521(8) 0.38281(15) 0.0536 1.0000 Uani . C29 C -0.0356(7) 0.3769(8) 0.36074(16) 0.0600 1.0000 Uani . C30 C 0.0596(7) 0.3129(8) 0.38852(16) 0.0525 1.0000 Uani . C31 C -0.3053(8) 0.1795(12) 0.14242(15) 0.0709 1.0000 Uani . C32 C -0.0615(7) 0.0663(8) 0.26292(14) 0.0549 1.0000 Uani . C33 C 0.1988(7) -0.5681(8) 0.06400(15) 0.0576 1.0000 Uani . C34 C 0.2844(7) 0.5389(8) 0.45549(15) 0.0592 1.0000 Uani . C35 C 0.0149(6) -0.2120(7) 0.22900(14) 0.0531 1.0000 Uani . C36 C -0.0506(7) 0.2828(9) 0.32993(15) 0.0582 1.0000 Uani . C37 C 0.1934(8) -0.6619(10) 0.03330(16) 0.0812 1.0000 Uani . C38 C 0.6148(8) 0.1776(9) 0.39022(18) 0.0759 1.0000 Uani . C39 C 0.2583(9) -0.1915(9) 0.04907(15) 0.0800 1.0000 Uani . C40 C 0.0579(7) -0.4936(8) 0.19573(15) 0.0689 1.0000 Uani . C41 C 0.4931(7) -0.5131(10) 0.06050(17) 0.0908 1.0000 Uani . N42 N -0.3704(8) 0.3140(9) 0.14292(16) 0.1029 1.0000 Uani . C43 C 0.2634(8) 0.6284(10) 0.48661(15) 0.0789 1.0000 Uani . C44 C -0.0388(9) 0.5463(10) 0.42764(17) 0.0867 1.0000 Uani . C45 C 0.6684(10) -0.0788(12) 0.35502(18) 0.0841 1.0000 Uani . C46 C -0.2281(8) -0.0718(9) 0.1078(2) 0.0764 1.0000 Uani . C47 C 0.3173(6) 0.6115(7) 0.30579(14) 0.0640 1.0000 Uani . C48 C 0.2007(7) 0.3685(8) 0.44447(16) 0.0640 1.0000 Uani . C49 C -0.2113(6) -0.4000(9) 0.20991(15) 0.0666 1.0000 Uani . C50 C 0.5768(6) 0.5190(8) 0.28559(14) 0.0611 1.0000 Uani . N51 N 0.6277(9) 0.2387(9) 0.41742(15) 0.1173 1.0000 Uani . N52 N -0.2291(9) -0.1405(9) 0.08171(16) 0.1105 1.0000 Uani . C53 C 0.0613(10) -0.5677(10) 0.08242(16) 0.0837 1.0000 Uani . C54 C 0.3395(13) 0.7906(12) 0.4944(2) 0.1052 1.0000 Uani . C55 C 0.4355(12) 0.8563(13) 0.4700(3) 0.1203 1.0000 Uani . C56 C 0.3865(10) 0.6115(11) 0.43245(19) 0.0942 1.0000 Uani . N57 N 0.7172(9) -0.2181(10) 0.35353(17) 0.1301 1.0000 Uani . C58 C 0.1383(9) 0.2614(11) 0.47454(19) 0.1138 1.0000 Uani . C59 C -0.0038(10) 0.7256(12) 0.4161(2) 0.1196 1.0000 Uani . C60 C 0.3840(9) -0.0778(11) 0.03461(16) 0.1052 1.0000 Uani . C61 C -0.0697(12) -0.7458(14) 0.0397(3) 0.1117 1.0000 Uani . C62 C 0.0581(13) -0.7475(11) 0.0214(2) 0.0997 1.0000 Uani . C63 C -0.0735(10) -0.6574(14) 0.0701(3) 0.1142 1.0000 Uani . C64 C 0.4576(10) 0.7721(16) 0.4394(3) 0.1258 1.0000 Uani . H41 H 0.4449 -0.3725 0.1399 0.0620 1.0000 Uiso R H71 H 0.5625 -0.0208 0.2935 0.0680 1.0000 Uiso R H101 H 0.4555 -0.2172 0.1914 0.0607 1.0000 Uiso R H111 H -0.1990 0.1371 0.2040 0.0661 1.0000 Uiso R H141 H 0.1728 -0.0459 0.3492 0.0702 1.0000 Uiso R H161 H 0.2148 0.0398 0.0945 0.0649 1.0000 Uiso R H171 H 0.2989 0.2122 0.2074 0.0587 1.0000 Uiso R H181 H 0.2392 0.3003 0.2798 0.0685 1.0000 Uiso R H182 H 0.3399 0.3844 0.2502 0.0684 1.0000 Uiso R H201 H 0.2282 0.1870 0.1459 0.0680 1.0000 Uiso R H221 H 0.5167 0.4254 0.3475 0.0658 1.0000 Uiso R H222 H 0.3525 0.3344 0.3447 0.0650 1.0000 Uiso R H232 H 0.0446 -0.2036 0.1594 0.0705 1.0000 Uiso R H231 H -0.1113 -0.3058 0.1488 0.0702 1.0000 Uiso R H251 H 0.4760 -0.0515 0.2378 0.0650 1.0000 Uiso R H271 H 0.0664 -0.0855 0.2922 0.0683 1.0000 Uiso R H281 H 0.1992 0.1026 0.4008 0.0645 1.0000 Uiso R H291 H -0.0882 0.4846 0.3630 0.0722 1.0000 Uiso R H321 H -0.1167 0.1737 0.2625 0.0671 1.0000 Uiso R H352 H 0.0110 -0.2739 0.2510 0.0657 1.0000 Uiso R H351 H 0.1225 -0.1902 0.2239 0.0650 1.0000 Uiso R H361 H -0.1149 0.3274 0.3123 0.0706 1.0000 Uiso R H391 H 0.2309 -0.2833 0.0322 0.0960 1.0000 Uiso R H392 H 0.1649 -0.1213 0.0533 0.0960 1.0000 Uiso R H401 H 0.0631 -0.5623 0.2170 0.1050 1.0000 Uiso R H402 H 0.1616 -0.4464 0.1909 0.1046 1.0000 Uiso R H403 H 0.0197 -0.5690 0.1766 0.1050 1.0000 Uiso R H413 H 0.5086 -0.6399 0.0601 0.1359 1.0000 Uiso R H411 H 0.5782 -0.4532 0.0728 0.1359 1.0000 Uiso R H412 H 0.4806 -0.4642 0.0372 0.1358 1.0000 Uiso R H442 H -0.0410 0.5474 0.4529 0.1060 1.0000 Uiso R H441 H -0.1430 0.5136 0.4177 0.1057 1.0000 Uiso R H471 H 0.3638 0.6899 0.3232 0.0962 1.0000 Uiso R H473 H 0.2183 0.5674 0.3139 0.0961 1.0000 Uiso R H472 H 0.2967 0.6758 0.2841 0.0959 1.0000 Uiso R H481 H 0.2788 0.2944 0.4325 0.0757 1.0000 Uiso R H493 H -0.1979 -0.4796 0.2293 0.1011 1.0000 Uiso R H492 H -0.2770 -0.3023 0.2165 0.1004 1.0000 Uiso R H491 H -0.2607 -0.4631 0.1908 0.1010 1.0000 Uiso R H503 H 0.6294 0.5977 0.3018 0.0932 1.0000 Uiso R H502 H 0.6452 0.4212 0.2807 0.0929 1.0000 Uiso R H501 H 0.5560 0.5818 0.2642 0.0928 1.0000 Uiso R H583 H 0.2214 0.2387 0.4912 0.1711 1.0000 Uiso R H582 H 0.0575 0.3304 0.4854 0.1708 1.0000 Uiso R H581 H 0.0943 0.1515 0.4658 0.1710 1.0000 Uiso R H591 H -0.0916 0.8020 0.4204 0.1791 1.0000 Uiso R H592 H 0.0885 0.7712 0.4281 0.1790 1.0000 Uiso R H593 H 0.0125 0.7254 0.3917 0.1790 1.0000 Uiso R H603 H 0.3548 -0.0397 0.0116 0.1578 1.0000 Uiso R H602 H 0.4797 -0.1450 0.0342 0.1582 1.0000 Uiso R H601 H 0.3979 0.0253 0.0492 0.1582 1.0000 Uiso R H371 H 0.2842 -0.6674 0.0201 0.0965 1.0000 Uiso . H431 H 0.1966 0.5780 0.5030 0.0953 1.0000 Uiso . H531 H 0.0606 -0.5041 0.1034 0.1004 1.0000 Uiso . H541 H 0.3236 0.8469 0.5153 0.1272 1.0000 Uiso . H551 H 0.4859 0.9651 0.4748 0.1426 1.0000 Uiso . H561 H 0.4049 0.5505 0.4115 0.1126 1.0000 Uiso . H611 H -0.1593 -0.8096 0.0312 0.1336 1.0000 Uiso . H621 H 0.0590 -0.8084 -0.0001 0.1186 1.0000 Uiso . H631 H -0.1640 -0.6569 0.0826 0.1365 1.0000 Uiso . H641 H 0.5232 0.8211 0.4229 0.1512 1.0000 Uiso . H261 H 0.3613 -0.5195 0.1043 0.0755 1.0000 Uiso . 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 0.091(4) 0.053(4) 0.032(3) -0.004(3) -0.001(3) 0.014(3) N2 0.058(3) 0.051(3) 0.070(4) -0.015(3) -0.012(3) 0.009(3) C3 0.054(4) 0.048(4) 0.029(3) -0.016(3) 0.006(3) 0.000(3) C4 0.063(4) 0.050(4) 0.043(4) -0.012(3) 0.007(3) 0.007(3) C5 0.046(4) 0.050(4) 0.057(4) -0.001(3) 0.003(3) 0.001(3) C6 0.044(3) 0.060(4) 0.046(3) -0.005(3) 0.006(3) 0.000(3) C7 0.074(4) 0.059(4) 0.035(4) -0.007(3) -0.002(3) -0.002(3) C8 0.058(4) 0.050(4) 0.038(3) 0.008(3) -0.001(3) 0.018(3) C9 0.052(4) 0.046(4) 0.042(4) -0.004(3) 0.006(3) 0.004(3) C10 0.054(4) 0.062(5) 0.036(3) 0.000(3) 0.002(3) 0.006(3) C11 0.052(4) 0.052(4) 0.061(4) 0.000(4) 0.009(3) 0.006(3) C12 0.043(4) 0.056(4) 0.052(4) 0.000(3) -0.004(3) 0.003(3) C13 0.062(4) 0.045(4) 0.045(4) 0.009(3) 0.008(3) -0.009(4) C14 0.073(4) 0.046(4) 0.054(4) -0.003(4) 0.000(3) -0.001(3) C15 0.065(4) 0.048(4) 0.059(4) 0.004(4) -0.011(3) -0.012(4) C16 0.069(4) 0.054(4) 0.040(4) 0.014(3) -0.002(3) 0.010(3) C17 0.050(4) 0.048(4) 0.050(4) 0.003(3) -0.002(3) 0.008(3) C18 0.062(4) 0.056(4) 0.052(4) -0.006(3) 0.000(3) -0.005(4) C19 0.079(4) 0.044(4) 0.052(4) -0.008(3) -0.013(3) -0.006(4) C20 0.067(4) 0.054(4) 0.045(4) 0.006(3) 0.003(3) 0.015(3) C21 0.053(4) 0.045(4) 0.047(4) 0.008(3) -0.002(3) -0.011(3) C22 0.064(4) 0.054(4) 0.041(4) -0.013(3) 0.011(3) -0.008(3) C23 0.062(4) 0.062(5) 0.055(4) 0.006(3) 0.007(3) 0.002(4) C24 0.063(4) 0.039(4) 0.046(3) 0.000(3) 0.005(3) 0.000(3) C25 0.063(4) 0.050(4) 0.050(4) -0.007(3) -0.007(3) 0.004(3) C26 0.080(4) 0.057(5) 0.043(3) -0.008(3) -0.018(3) 0.008(4) C27 0.051(4) 0.060(4) 0.057(4) -0.009(4) 0.007(3) 0.005(3) C28 0.064(4) 0.038(4) 0.058(4) 0.002(3) -0.005(3) 0.001(3) C29 0.054(4) 0.054(4) 0.072(4) -0.005(3) 0.004(4) 0.008(3) C30 0.050(4) 0.049(4) 0.058(4) -0.004(4) -0.004(3) -0.012(3) C31 0.079(5) 0.076(6) 0.057(4) 0.020(4) -0.022(4) -0.008(5) C32 0.065(4) 0.060(4) 0.040(4) -0.007(3) -0.001(3) 0.007(3) C33 0.067(4) 0.055(4) 0.050(4) -0.002(3) -0.005(3) 0.025(4) C34 0.058(4) 0.063(4) 0.056(4) -0.002(4) -0.007(3) 0.017(3) C35 0.054(4) 0.055(4) 0.051(4) -0.003(3) 0.001(3) 0.007(3) C36 0.056(4) 0.066(5) 0.052(4) 0.004(4) -0.007(3) 0.009(4) C37 0.089(5) 0.098(6) 0.055(4) -0.017(4) -0.018(4) 0.004(5) C38 0.115(6) 0.057(5) 0.055(4) 0.006(4) -0.019(4) -0.021(4) C39 0.120(6) 0.074(5) 0.044(4) -0.006(4) -0.015(4) 0.022(5) C40 0.071(4) 0.050(4) 0.086(5) -0.007(3) 0.010(4) 0.014(4) C41 0.056(4) 0.107(6) 0.111(5) -0.024(5) 0.019(4) 0.010(4) N42 0.122(5) 0.075(5) 0.110(5) 0.022(4) -0.028(4) 0.009(4) C43 0.109(5) 0.080(6) 0.047(4) -0.011(4) -0.020(3) 0.025(5) C44 0.110(6) 0.076(6) 0.073(5) -0.012(4) -0.018(4) -0.019(5) C45 0.111(6) 0.086(7) 0.053(4) 0.001(5) -0.037(4) 0.002(5) C46 0.104(5) 0.055(5) 0.068(5) 0.007(4) -0.015(4) -0.007(4) C47 0.065(4) 0.051(4) 0.076(4) -0.014(3) 0.007(3) 0.015(4) C48 0.074(4) 0.055(4) 0.063(4) 0.002(3) -0.009(4) 0.005(4) C49 0.057(4) 0.075(4) 0.069(4) 0.003(3) 0.017(3) -0.002(4) C50 0.061(4) 0.057(4) 0.066(4) 0.005(3) 0.010(3) 0.006(3) N51 0.191(7) 0.104(5) 0.054(4) -0.002(4) -0.030(4) -0.027(5) N52 0.168(7) 0.096(5) 0.067(4) -0.005(4) -0.011(4) -0.016(5) C53 0.082(5) 0.102(6) 0.067(4) 0.014(4) 0.001(4) 0.014(5) C54 0.139(8) 0.085(7) 0.087(6) -0.021(5) -0.059(6) 0.044(6) C55 0.110(7) 0.120(8) 0.127(9) -0.017(8) -0.050(7) -0.009(7) C56 0.113(6) 0.085(6) 0.085(5) -0.020(4) 0.003(5) -0.025(5) N57 0.188(7) 0.085(5) 0.111(5) -0.014(5) -0.082(5) 0.044(6) C58 0.126(6) 0.100(6) 0.116(6) 0.029(5) 0.019(5) -0.008(5) C59 0.137(7) 0.099(7) 0.119(7) -0.009(5) -0.050(6) 0.009(6) C60 0.147(7) 0.107(6) 0.064(5) 0.020(4) 0.033(5) 0.022(6) C61 0.101(7) 0.125(8) 0.108(7) 0.024(6) -0.017(7) -0.026(6) C62 0.104(6) 0.101(6) 0.091(6) -0.018(5) -0.039(6) 0.014(6) C63 0.073(6) 0.156(9) 0.114(7) 0.046(7) 0.006(6) 0.009(6) C64 0.113(7) 0.151(10) 0.114(7) 0.005(7) 0.024(6) -0.048(7) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 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_publ_flag C8 N1 C26 122.5(5) yes C8 N1 C39 119.2(5) yes C26 N1 C39 118.3(5) yes C30 N2 C44 121.3(5) yes C30 N2 C48 121.5(5) yes C44 N2 C48 116.6(5) yes C10 C3 C17 123.0(5) yes C10 C3 C20 115.8(5) yes C17 C3 C20 121.2(6) yes C8 C4 C10 121.2(5) yes C8 C4 H41 118.3 no C10 C4 H41 120.5 no C14 C5 C27 120.3(6) yes C14 C5 C36 115.7(5) yes C27 C5 C36 124.0(5) yes C23 C6 C35 108.5(5) yes C23 C6 C40 108.4(5) yes C35 C6 C40 110.2(4) yes C23 C6 C49 110.5(5) yes C35 C6 C49 109.8(4) yes C40 C6 C49 109.4(5) yes C9 C7 C13 123.9(6) yes C9 C7 H71 116.9 no C13 C7 H71 119.2 no C4 C8 N1 121.8(5) yes C4 C8 C16 116.0(5) yes N1 C8 C16 122.1(5) yes C7 C9 C18 119.6(5) yes C7 C9 C25 119.6(6) yes C18 C9 C25 120.8(5) yes C3 C10 C4 122.7(5) yes C3 C10 H101 118.6 no C4 C10 H101 118.7 no C12 C11 C21 124.1(6) yes C12 C11 H111 117.9 no C21 C11 H111 118.0 no C11 C12 C32 121.0(6) yes C11 C12 C35 118.6(5) yes C32 C12 C35 120.4(5) yes C7 C13 C19 121.9(6) yes C7 C13 C22 118.5(5) yes C19 C13 C22 119.6(6) yes C5 C14 C28 122.0(6) yes C5 C14 H141 118.0 no C28 C14 H141 120.0 no C21 C15 C31 121.6(6) yes C21 C15 C46 123.5(6) yes C31 C15 C46 114.9(6) yes C8 C16 C20 121.0(5) yes C8 C16 H161 119.6 no C20 C16 H161 119.4 no C3 C17 C25 127.9(6) yes C3 C17 H171 117.4 no C25 C17 H171 114.7 no C9 C18 C24 114.1(4) yes C9 C18 H181 107.7 no C24 C18 H181 107.8 no C9 C18 H182 109.5 no C24 C18 H182 109.1 no H181 C18 H182 108.5 no C13 C19 C38 123.1(6) yes C13 C19 C45 121.9(6) yes C38 C19 C45 115.0(6) yes C3 C20 C16 123.2(5) yes C3 C20 H201 119.0 no C16 C20 H201 117.8 no C11 C21 C15 122.4(6) yes C11 C21 C23 118.1(5) yes C15 C21 C23 119.5(6) yes C13 C22 C24 114.8(5) yes C13 C22 H221 110.5 no C24 C22 H221 104.1 no C13 C22 H222 109.2 no C24 C22 H222 108.6 no H221 C22 H222 109.4 no C6 C23 C21 113.0(5) yes C6 C23 H232 108.7 no C21 C23 H232 108.0 no C6 C23 H231 108.1 no C21 C23 H231 110.5 no H232 C23 H231 108.4 no C22 C24 C18 108.1(5) yes C22 C24 C47 110.1(5) yes C18 C24 C47 110.8(4) yes C22 C24 C50 110.6(4) yes C18 C24 C50 108.3(4) yes C47 C24 C50 108.9(5) yes C9 C25 C17 128.3(6) yes C9 C25 H251 114.9 no C17 C25 H251 116.7 no N1 C26 C33 107.0(5) yes N1 C26 C41 113.2(5) yes C33 C26 C41 114.2(5) yes N1 C26 H261 107.6 no C33 C26 H261 107.6 no C41 C26 H261 107.0 no C5 C27 C32 129.2(6) yes C5 C27 H271 116.6 no C32 C27 H271 114.2 no C14 C28 C30 122.5(5) yes C14 C28 H281 118.4 no C30 C28 H281 119.1 no C30 C29 C36 120.8(6) yes C30 C29 H291 119.7 no C36 C29 H291 119.4 no C29 C30 C28 115.9(6) yes C29 C30 N2 120.0(6) yes C28 C30 N2 124.1(6) yes C15 C31 N42 178.9(8) yes C12 C32 C27 127.7(6) yes C12 C32 H321 115.8 no C27 C32 H321 116.5 no C26 C33 C37 124.9(6) yes C26 C33 C53 119.3(6) yes C37 C33 C53 115.7(6) yes C43 C34 C48 125.1(7) yes C43 C34 C56 117.8(6) yes C48 C34 C56 117.1(6) yes C6 C35 C12 114.3(4) yes C6 C35 H352 108.5 no C12 C35 H352 110.5 no C6 C35 H351 106.7 no C12 C35 H351 107.7 no H352 C35 H351 108.8 no C5 C36 C29 123.0(5) yes C5 C36 H361 118.2 no C29 C36 H361 118.8 no C33 C37 C62 121.6(7) yes C33 C37 H371 118.7 no C62 C37 H371 119.7 no C19 C38 N51 177.9(8) yes N1 C39 C60 113.3(5) yes N1 C39 H391 106.8 no C60 C39 H391 108.5 no N1 C39 H392 108.8 no C60 C39 H392 110.9 no H391 C39 H392 108.4 no C6 C40 H401 109.1 no C6 C40 H402 107.3 no H401 C40 H402 109.8 no C6 C40 H403 110.7 no H401 C40 H403 109.5 no H402 C40 H403 110.4 no C26 C41 H413 108.4 no C26 C41 H411 107.8 no H413 C41 H411 111.5 no C26 C41 H412 107.7 no H413 C41 H412 111.7 no H411 C41 H412 109.5 no C34 C43 C54 122.0(8) yes C34 C43 H431 118.6 no C54 C43 H431 119.4 no N2 C44 C59 114.4(7) yes N2 C44 H442 106.9 no C59 C44 H442 108.0 no N2 C44 H441 109.9 no C59 C44 H441 107.7 no H442 C44 H441 109.9 no C19 C45 N57 178.0(9) yes C15 C46 N52 178.6(8) yes C24 C47 H471 110.8 no C24 C47 H473 108.0 no H471 C47 H473 109.2 no C24 C47 H472 110.3 no H471 C47 H472 110.4 no H473 C47 H472 108.1 no C34 C48 N2 109.2(5) yes C34 C48 C58 114.0(5) yes N2 C48 C58 112.5(6) yes C34 C48 H481 106.5 no N2 C48 H481 106.0 no C58 C48 H481 108.2 no C6 C49 H493 107.8 no C6 C49 H492 110.8 no H493 C49 H492 109.0 no C6 C49 H491 110.8 no H493 C49 H491 109.1 no H492 C49 H491 109.4 no C24 C50 H503 111.1 no C24 C50 H502 111.1 no H503 C50 H502 108.9 no C24 C50 H501 109.0 no H503 C50 H501 109.0 no H502 C50 H501 107.6 no C33 C53 C63 121.6(7) yes C33 C53 H531 118.0 no C63 C53 H531 120.4 no C43 C54 C55 116.8(8) yes C43 C54 H541 120.1 no C55 C54 H541 123.1 no C54 C55 C64 122.4(9) yes C54 C55 H551 117.4 no C64 C55 H551 120.2 no C34 C56 C64 120.5(8) yes C34 C56 H561 119.0 no C64 C56 H561 120.5 no C48 C58 H583 109.4 no C48 C58 H582 108.6 no H583 C58 H582 109.3 no C48 C58 H581 109.4 no H583 C58 H581 110.7 no H582 C58 H581 109.5 no C44 C59 H591 109.3 no C44 C59 H592 110.8 no H591 C59 H592 109.4 no C44 C59 H593 109.8 no H591 C59 H593 108.2 no H592 C59 H593 109.3 no C39 C60 H603 110.3 no C39 C60 H602 109.1 no H603 C60 H602 109.8 no C39 C60 H601 108.5 no H603 C60 H601 109.0 no H602 C60 H601 110.1 no C62 C61 C63 120.9(9) yes C62 C61 H611 118.9 no C63 C61 H611 120.3 no C37 C62 C61 121.1(8) yes C37 C62 H621 118.7 no C61 C62 H621 120.2 no C53 C63 C61 119.2(8) yes C53 C63 H631 120.8 no C61 C63 H631 120.0 no C56 C64 C55 120.4(9) yes C56 C64 H641 119.0 no C55 C64 H641 120.6 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C8 1.358(6) yes N1 C26 1.479(7) yes N1 C39 1.465(7) yes N2 C30 1.362(7) yes N2 C44 1.483(8) yes N2 C48 1.471(6) yes C3 C10 1.379(7) yes C3 C17 1.439(7) yes C3 C20 1.394(7) yes C4 C8 1.421(7) yes C4 C10 1.374(7) yes C4 H41 0.944 no C5 C14 1.395(7) yes C5 C27 1.431(7) yes C5 C36 1.387(8) yes C6 C23 1.526(7) yes C6 C35 1.527(7) yes C6 C40 1.533(7) yes C6 C49 1.512(7) yes C7 C9 1.346(7) yes C7 C13 1.424(7) yes C7 H71 0.928 no C8 C16 1.396(8) yes C9 C18 1.489(7) yes C9 C25 1.431(7) yes C10 H101 0.938 no C11 C12 1.367(7) yes C11 C21 1.416(7) yes C11 H111 0.933 no C12 C32 1.437(7) yes C12 C35 1.517(7) yes C13 C19 1.350(7) yes C13 C22 1.484(7) yes C14 C28 1.373(7) yes C14 H141 0.930 no C15 C21 1.358(7) yes C15 C31 1.438(10) yes C15 C46 1.431(9) yes C16 C20 1.373(7) yes C16 H161 0.945 no C17 C25 1.346(6) yes C17 H171 0.939 no C18 C24 1.543(7) yes C18 H181 0.982 no C18 H182 0.970 no C19 C38 1.419(8) yes C19 C45 1.439(10) yes C20 H201 0.932 no C21 C23 1.510(7) yes C22 C24 1.541(7) yes C22 H221 0.955 no C22 H222 0.960 no C23 H232 0.972 no C23 H231 0.978 no C24 C47 1.515(7) yes C24 C50 1.528(7) yes C25 H251 0.930 no C26 C33 1.531(8) yes C26 C41 1.516(8) yes C26 H261 1.023 no C27 C32 1.332(7) yes C27 H271 0.943 no C28 C30 1.393(8) yes C28 H281 0.945 no C29 C30 1.408(7) yes C29 C36 1.385(7) yes C29 H291 0.932 no C31 N42 1.154(9) yes C32 H321 0.935 no C33 C37 1.377(8) yes C33 C53 1.393(8) yes C34 C43 1.392(8) yes C34 C48 1.521(8) yes C34 C56 1.379(9) yes C35 H352 0.968 no C35 H351 0.961 no C36 H361 0.923 no C37 C62 1.389(10) yes C37 H371 0.942 no C38 N51 1.147(7) yes C39 C60 1.496(9) yes C39 H391 0.973 no C39 H392 0.976 no C40 H401 0.967 no C40 H402 0.979 no C40 H403 0.976 no C41 H413 0.963 no C41 H411 0.967 no C41 H412 0.972 no C43 C54 1.410(11) yes C43 H431 0.944 no C44 C59 1.454(9) yes C44 H442 0.975 no C44 H441 0.989 no C45 N57 1.130(9) yes C46 N52 1.130(7) yes C47 H471 0.968 no C47 H473 0.970 no C47 H472 0.975 no C48 C58 1.523(8) yes C48 H481 0.995 no C49 H493 0.961 no C49 H492 0.964 no C49 H491 0.963 no C50 H503 0.962 no C50 H502 0.962 no C50 H501 0.963 no C53 C63 1.406(10) yes C53 H531 0.939 no C54 C55 1.362(12) yes C54 H541 0.924 no C55 C64 1.357(12) yes C55 H551 0.941 no C56 C64 1.374(11) yes C56 H561 0.946 no C58 H583 0.956 no C58 H582 0.970 no C58 H581 0.964 no C59 H591 0.965 no C59 H592 0.965 no C59 H593 0.956 no C60 H603 0.957 no C60 H602 0.962 no C60 H601 0.964 no C61 C62 1.320(10) yes C61 C63 1.347(11) yes C61 H611 0.952 no C62 H621 0.950 no C63 H631 0.925 no C64 H641 0.937 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C50 H503 N57 1_565 167 0.96 2.52 3.464(9) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30658421 2 PubChem 168327393