#------------------------------------------------------------------------------ #$Date: 2014-03-14 10:39:55 +0200 (Fri, 14 Mar 2014) $ #$Revision: 105906 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/21/7112138.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_7112138 loop_ _publ_author_name 'Thomas Hjelmgaard' 'Olivier Roy' 'Lionel Nauton' 'Malika El-Ghozzi' 'Daniel Avignant' 'Claude Didierjean' 'Claude Taillefumier' 'Sophie Faure' _publ_section_title ; Macrocyclic arylopeptoids -- a novel type of cyclic N-alkylated aromatic oligoamides forming nanotubular assemblies ; _journal_name_full Chem.Commun. _journal_page_first 3564 _journal_paper_doi 10.1039/C4CC00821A _journal_volume 50 _journal_year 2014 _chemical_formula_moiety 'C33 H39 N3 O3' _chemical_formula_sum 'C33 H39 N3 O3' _chemical_formula_weight 525.69 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _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 _cell_angle_alpha 90 _cell_angle_beta 91.413(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.8222(3) _cell_length_b 16.1122(6) _cell_length_c 27.2257(10) _cell_measurement_reflns_used 704 _cell_measurement_temperature 296 _cell_measurement_theta_max 15.35 _cell_measurement_theta_min 2.89 _cell_volume 3430.3(2) _computing_cell_refinement 'SAINT (Bruker 2008)' _computing_data_collection 'APEX II (Bruker 2008)' _computing_data_reduction SAINT _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 296 _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEXII CCD diffractometer' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.072 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 9408 _diffrn_reflns_theta_full 23.092 _diffrn_reflns_theta_max 23.092 _diffrn_reflns_theta_min 1.469 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_T_max 0.7441 _exptl_absorpt_correction_T_min 0.6621 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.018 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1128 _exptl_crystal_size_max 1.61 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.22 _refine_diff_density_min -0.29 _refine_ls_extinction_coef 400(100) _refine_ls_extinction_method 'Larson (1970), Equation 22' _refine_ls_goodness_of_fit_ref 1.0713 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 353 _refine_ls_number_reflns 5126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1027 _refine_ls_R_factor_gt 0.0663 _refine_ls_shift/su_max 0.0001785 _refine_ls_shift/su_mean 0.0000168 _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: 0.682 0.953 0.594 0.259 0.100 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1180 _refine_ls_wR_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.0596 _reflns_limit_h_max 8 _reflns_limit_h_min -8 _reflns_limit_k_max 17 _reflns_limit_k_min -17 _reflns_limit_l_max 30 _reflns_limit_l_min 0 _reflns_number_gt 6192 _reflns_number_total 9408 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 3.73 _oxford_diffrn_Wilson_scale 73.88 _oxford_refine_ls_r_factor_ref 0.0566 _oxford_refine_ls_scale 0.1412(3) _oxford_reflns_number_all 9368 _oxford_reflns_threshold_expression_ref I>0.0\s(I) _[local]_cod_data_source_file c4cc00821a.cif _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_Hall '-p 2ybc' _cod_database_code 7112138 _iucr_refine_instruction_details_constraints ; BLOCK SCALE X'S, U'S CONT EXTPARAM RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) H ( 82,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) H ( 102,X'S) H ( 103,X'S) RIDE C ( 11,X'S) H ( 111,X'S) H ( 112,X'S) H ( 113,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 19,X'S) H ( 191,X'S) H ( 192,X'S) RIDE C ( 20,X'S) H ( 201,X'S) RIDE C ( 21,X'S) H ( 211,X'S) H ( 212,X'S) H ( 213,X'S) RIDE C ( 22,X'S) H ( 221,X'S) H ( 222,X'S) H ( 223,X'S) RIDE C ( 25,X'S) H ( 251,X'S) RIDE C ( 26,X'S) H ( 261,X'S) RIDE C ( 27,X'S) H ( 271,X'S) RIDE C ( 29,X'S) H ( 291,X'S) RIDE C ( 30,X'S) H ( 301,X'S) H ( 302,X'S) RIDE C ( 31,X'S) H ( 311,X'S) RIDE C ( 32,X'S) H ( 321,X'S) H ( 322,X'S) H ( 323,X'S) RIDE C ( 33,X'S) H ( 331,X'S) H ( 332,X'S) H ( 333,X'S) END ; _iucr_refine_instruction_details_restraints ; NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn C1 C 0.3191(3) 0.22704(13) 0.42825(9) 0.0541 1.0000 Uani . C2 C 0.3753(2) 0.27364(13) 0.38368(9) 0.0487 1.0000 Uani . C3 C 0.4576(3) 0.34873(14) 0.38971(10) 0.0643 1.0000 Uani . C4 C 0.5194(4) 0.38934(16) 0.34949(12) 0.0765 1.0000 Uani . C5 C 0.5013(3) 0.35562(13) 0.30357(11) 0.0632 1.0000 Uani . C6 C 0.4212(3) 0.27953(12) 0.29648(9) 0.0508 1.0000 Uani . C7 C 0.3584(3) 0.23953(13) 0.33708(9) 0.0531 1.0000 Uani . C8 C 0.4022(4) 0.24751(15) 0.24513(10) 0.0798 1.0000 Uani . C9 C 0.4997(3) 0.10119(17) 0.22634(10) 0.0671 1.0000 Uani . C10 C 0.6423(4) 0.0998(3) 0.26523(14) 0.1238 1.0000 Uani . C11 C 0.5673(4) 0.1213(2) 0.17572(12) 0.1058 1.0000 Uani . C12 C 0.1964(3) 0.13730(13) 0.23998(9) 0.0519 1.0000 Uani . C13 C 0.1444(3) 0.04935(13) 0.23133(9) 0.0480 1.0000 Uani . C14 C 0.0565(3) 0.02837(16) 0.18837(10) 0.0675 1.0000 Uani . C15 C -0.0032(4) -0.05237(19) 0.18236(12) 0.0812 1.0000 Uani . C16 C 0.0221(3) -0.10994(16) 0.21874(11) 0.0700 1.0000 Uani . C17 C 0.1080(3) -0.09007(13) 0.26184(9) 0.0525 1.0000 Uani . C18 C 0.1693(3) -0.00914(12) 0.26784(9) 0.0481 1.0000 Uani . C19 C 0.1334(3) -0.15534(13) 0.30098(10) 0.0641 1.0000 Uani . C20 C -0.0433(3) -0.12641(15) 0.37464(10) 0.0636 1.0000 Uani . C21 C -0.1756(3) -0.07540(19) 0.34600(12) 0.0835 1.0000 Uani . C22 C -0.1022(4) -0.2151(2) 0.38259(13) 0.1042 1.0000 Uani . C23 C 0.2702(3) -0.10582(15) 0.37553(12) 0.0662 1.0000 Uani . C24 C 0.2606(3) -0.06294(14) 0.42401(11) 0.0605 1.0000 Uani . C25 C 0.3277(3) -0.09841(19) 0.46641(15) 0.0765 1.0000 Uani . C26 C 0.3247(3) -0.0562(2) 0.50980(14) 0.0789 1.0000 Uani . C27 C 0.2583(3) 0.02306(19) 0.51178(10) 0.0691 1.0000 Uani . C28 C 0.1926(3) 0.06138(15) 0.46964(10) 0.0565 1.0000 Uani . C29 C 0.1943(3) 0.01718(15) 0.42617(10) 0.0596 1.0000 Uani . C30 C 0.1153(3) 0.14661(15) 0.47206(9) 0.0655 1.0000 Uani . C31 C 0.0144(3) 0.24142(15) 0.40336(10) 0.0611 1.0000 Uani . C32 C -0.0993(3) 0.18097(19) 0.37514(11) 0.0879 1.0000 Uani . C33 C -0.0881(4) 0.2955(2) 0.43760(13) 0.1050 1.0000 Uani . O34 O 0.4233(2) 0.21148(12) 0.46109(7) 0.0837 1.0000 Uani . O35 O 0.0842(2) 0.18932(10) 0.24674(8) 0.0836 1.0000 Uani . O36 O 0.4097(2) -0.11990(15) 0.35723(10) 0.1177 1.0000 Uani . N37 N 0.3620(3) 0.15848(10) 0.23993(7) 0.0563 1.0000 Uani . N38 N 0.1238(2) -0.12388(10) 0.35095(8) 0.0544 1.0000 Uani . N39 N 0.1555(2) 0.19979(11) 0.42974(7) 0.0530 1.0000 Uani . H31 H 0.4705 0.3756 0.4216 0.0802 1.0000 Uiso R H41 H 0.5792 0.4422 0.3550 0.0909 1.0000 Uiso R H51 H 0.5457 0.3826 0.2751 0.0784 1.0000 Uiso R H71 H 0.3011 0.1864 0.3335 0.0646 1.0000 Uiso R H81 H 0.5068 0.2586 0.2271 0.1048 1.0000 Uiso R H82 H 0.3102 0.2779 0.2276 0.1060 1.0000 Uiso R H91 H 0.4491 0.0450 0.2251 0.0873 1.0000 Uiso R H101 H 0.5932 0.0920 0.2968 0.1942 1.0000 Uiso R H102 H 0.7025 0.1514 0.2631 0.1943 1.0000 Uiso R H103 H 0.7158 0.0543 0.2575 0.1936 1.0000 Uiso R H111 H 0.4741 0.1278 0.1527 0.1709 1.0000 Uiso R H112 H 0.6322 0.1725 0.1759 0.1711 1.0000 Uiso R H113 H 0.6400 0.0773 0.1648 0.1710 1.0000 Uiso R H141 H 0.0396 0.0716 0.1620 0.0854 1.0000 Uiso R H151 H -0.0657 -0.0658 0.1525 0.0996 1.0000 Uiso R H161 H -0.0202 -0.1660 0.2148 0.0872 1.0000 Uiso R H181 H 0.2354 0.0063 0.2975 0.0621 1.0000 Uiso R H191 H 0.2480 -0.1804 0.2983 0.0814 1.0000 Uiso R H192 H 0.0420 -0.1992 0.2962 0.0806 1.0000 Uiso R H201 H -0.0296 -0.0981 0.4087 0.0834 1.0000 Uiso R H211 H -0.1375 -0.0184 0.3444 0.1335 1.0000 Uiso R H212 H -0.2804 -0.0767 0.3631 0.1337 1.0000 Uiso R H213 H -0.1875 -0.0986 0.3126 0.1334 1.0000 Uiso R H221 H -0.0128 -0.2436 0.4011 0.1601 1.0000 Uiso R H222 H -0.2032 -0.2132 0.4022 0.1596 1.0000 Uiso R H223 H -0.1279 -0.2415 0.3508 0.1601 1.0000 Uiso R H251 H 0.3791 -0.1535 0.4651 0.0958 1.0000 Uiso R H261 H 0.3710 -0.0838 0.5397 0.0960 1.0000 Uiso R H271 H 0.2572 0.0529 0.5423 0.0902 1.0000 Uiso R H291 H 0.1461 0.0418 0.3966 0.0743 1.0000 Uiso R H301 H 0.1559 0.1741 0.5041 0.0849 1.0000 Uiso R H302 H -0.0119 0.1421 0.4733 0.0847 1.0000 Uiso R H311 H 0.0668 0.2786 0.3778 0.0788 1.0000 Uiso R H321 H -0.0355 0.1535 0.3493 0.1398 1.0000 Uiso R H322 H -0.1436 0.1410 0.3978 0.1404 1.0000 Uiso R H323 H -0.1950 0.2113 0.3607 0.1402 1.0000 Uiso R H331 H -0.0043 0.3286 0.4552 0.1623 1.0000 Uiso R H332 H -0.1498 0.2596 0.4591 0.1636 1.0000 Uiso R H333 H -0.1590 0.3328 0.4184 0.1632 1.0000 Uiso 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 C1 0.0546(15) 0.0438(13) 0.0632(17) -0.0019(12) -0.0107(13) -0.0049(11) C2 0.0382(12) 0.0392(12) 0.0682(17) 0.0029(12) -0.0056(11) -0.0018(10) C3 0.0712(16) 0.0469(14) 0.0748(19) -0.0063(13) 0.0035(14) -0.0115(12) C4 0.0845(19) 0.0466(15) 0.099(2) -0.0119(16) 0.0059(17) -0.0274(13) C5 0.0673(16) 0.0385(13) 0.084(2) 0.0034(13) 0.0190(14) -0.0132(11) C6 0.0511(13) 0.0327(12) 0.0691(17) 0.0052(11) 0.0108(12) -0.0074(10) C7 0.0581(14) 0.0348(12) 0.0666(17) 0.0025(12) 0.0036(12) -0.0129(10) C8 0.117(2) 0.0492(15) 0.074(2) 0.0019(14) 0.0192(17) -0.0340(15) C9 0.0519(15) 0.0716(17) 0.078(2) -0.0053(14) 0.0104(14) -0.0110(12) C10 0.074(2) 0.180(4) 0.116(3) -0.024(3) -0.010(2) 0.013(2) C11 0.121(3) 0.101(2) 0.097(3) -0.0146(19) 0.047(2) -0.021(2) C12 0.0612(16) 0.0367(13) 0.0579(16) 0.0045(10) 0.0069(12) 0.0040(12) C13 0.0415(12) 0.0412(12) 0.0618(16) -0.0007(12) 0.0084(11) 0.0005(10) C14 0.0703(17) 0.0634(17) 0.0686(19) 0.0002(13) -0.0012(15) -0.0011(13) C15 0.083(2) 0.078(2) 0.082(2) -0.0190(17) -0.0066(16) -0.0225(16) C16 0.0748(18) 0.0492(15) 0.087(2) -0.0134(16) 0.0141(16) -0.0179(13) C17 0.0420(13) 0.0447(14) 0.0717(18) -0.0084(12) 0.0170(12) -0.0033(10) C18 0.0453(13) 0.0343(12) 0.0651(16) -0.0034(11) 0.0083(11) -0.0034(10) C19 0.0649(16) 0.0346(12) 0.094(2) -0.0039(13) 0.0213(14) -0.0043(11) C20 0.0493(14) 0.0646(16) 0.0774(18) -0.0067(13) 0.0115(13) -0.0186(12) C21 0.0456(15) 0.109(2) 0.097(2) -0.0049(18) 0.0059(14) 0.0022(15) C22 0.115(3) 0.094(2) 0.104(3) 0.0058(18) 0.019(2) -0.056(2) C23 0.0430(15) 0.0465(14) 0.109(2) 0.0099(15) 0.0015(15) -0.0002(11) C24 0.0361(13) 0.0487(15) 0.096(2) 0.0173(15) -0.0108(13) -0.0084(10) C25 0.0440(15) 0.0685(18) 0.117(3) 0.038(2) -0.0098(16) -0.0106(13) C26 0.0527(16) 0.090(2) 0.093(3) 0.050(2) -0.0049(16) -0.0130(15) C27 0.0511(15) 0.096(2) 0.0598(17) 0.0263(15) -0.0001(13) -0.0232(14) C28 0.0459(13) 0.0639(15) 0.0596(18) 0.0129(14) 0.0019(12) -0.0151(11) C29 0.0506(14) 0.0576(15) 0.0699(18) 0.0176(14) -0.0101(12) -0.0076(11) C30 0.0696(17) 0.0725(17) 0.0547(17) 0.0050(13) 0.0075(13) -0.0077(13) C31 0.0489(13) 0.0654(15) 0.0689(16) 0.0037(13) 0.0014(12) 0.0016(12) C32 0.0691(19) 0.100(2) 0.094(2) 0.0005(18) -0.0139(16) -0.0194(16) C33 0.087(2) 0.105(2) 0.123(3) -0.012(2) 0.002(2) 0.0311(19) O34 0.0757(12) 0.0853(13) 0.0884(14) 0.0212(11) -0.0330(11) -0.0208(10) O35 0.0860(13) 0.0486(10) 0.1163(16) 0.0007(10) 0.0028(11) 0.0252(10) O36 0.0445(12) 0.1263(18) 0.183(3) -0.0335(17) 0.0139(13) 0.0111(11) N37 0.0678(13) 0.0356(10) 0.0661(14) 0.0004(9) 0.0163(10) -0.0114(9) N38 0.0473(12) 0.0381(10) 0.0783(15) 0.0034(10) 0.0099(10) -0.0026(8) N39 0.0512(12) 0.0524(11) 0.0555(13) 0.0043(9) 0.0015(9) -0.0040(9) 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' 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' 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' 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 C2 C1 O34 119.4(2) yes C2 C1 N39 118.8(2) yes O34 C1 N39 121.7(2) yes C1 C2 C3 119.2(2) yes C1 C2 C7 121.20(19) yes C3 C2 C7 119.4(2) yes C2 C3 C4 119.7(3) yes C2 C3 H31 122.3 no C4 C3 H31 117.9 no C3 C4 C5 120.6(2) yes C3 C4 H41 117.9 no C5 C4 H41 121.5 no C4 C5 C6 121.0(2) yes C4 C5 H51 121.7 no C6 C5 H51 117.3 no C5 C6 C7 118.0(2) yes C5 C6 C8 118.0(2) yes C7 C6 C8 123.97(19) yes C2 C7 C6 121.3(2) yes C2 C7 H71 118.4 no C6 C7 H71 120.3 no C6 C8 N37 116.2(2) yes C6 C8 H81 109.8 no N37 C8 H81 107.9 no C6 C8 H82 109.7 no N37 C8 H82 106.6 no H81 C8 H82 106.0 no C10 C9 C11 111.6(3) yes C10 C9 N37 111.3(2) yes C11 C9 N37 111.5(2) yes C10 C9 H91 107.3 no C11 C9 H91 108.1 no N37 C9 H91 106.8 no C9 C10 H101 108.8 no C9 C10 H102 107.4 no H101 C10 H102 112.1 no C9 C10 H103 107.0 no H101 C10 H103 110.6 no H102 C10 H103 110.6 no C9 C11 H111 109.9 no C9 C11 H112 111.7 no H111 C11 H112 107.6 no C9 C11 H113 110.1 no H111 C11 H113 109.0 no H112 C11 H113 108.4 no C13 C12 O35 118.5(2) yes C13 C12 N37 120.13(19) yes O35 C12 N37 121.3(2) yes C12 C13 C14 119.6(2) yes C12 C13 C18 120.1(2) yes C14 C13 C18 120.0(2) yes C13 C14 C15 119.1(3) yes C13 C14 H141 119.2 no C15 C14 H141 121.7 no C14 C15 C16 120.5(3) yes C14 C15 H151 118.2 no C16 C15 H151 121.4 no C15 C16 C17 121.3(2) yes C15 C16 H161 120.7 no C17 C16 H161 118.1 no C16 C17 C18 118.4(2) yes C16 C17 C19 119.6(2) yes C18 C17 C19 122.0(2) yes C17 C18 C13 120.7(2) yes C17 C18 H181 120.3 no C13 C18 H181 118.9 no C17 C19 N38 114.15(18) yes C17 C19 H191 109.7 no N38 C19 H191 106.2 no C17 C19 H192 108.4 no N38 C19 H192 108.1 no H191 C19 H192 110.2 no C21 C20 C22 112.1(2) yes C21 C20 N38 111.1(2) yes C22 C20 N38 111.4(2) yes C21 C20 H201 106.0 no C22 C20 H201 108.1 no N38 C20 H201 107.9 no C20 C21 H211 109.3 no C20 C21 H212 108.7 no H211 C21 H212 108.2 no C20 C21 H213 108.4 no H211 C21 H213 110.0 no H212 C21 H213 112.3 no C20 C22 H221 107.7 no C20 C22 H222 107.8 no H221 C22 H222 108.6 no C20 C22 H223 109.8 no H221 C22 H223 112.5 no H222 C22 H223 110.4 no C24 C23 O36 120.5(2) yes C24 C23 N38 118.6(2) yes O36 C23 N38 120.7(3) yes C23 C24 C25 121.4(3) yes C23 C24 C29 119.5(2) yes C25 C24 C29 118.9(3) yes C24 C25 C26 120.2(3) yes C24 C25 H251 119.6 no C26 C25 H251 120.1 no C25 C26 C27 120.6(3) yes C25 C26 H261 118.3 no C27 C26 H261 121.1 no C26 C27 C28 120.7(3) yes C26 C27 H271 120.6 no C28 C27 H271 118.7 no C27 C28 C29 117.8(3) yes C27 C28 C30 120.7(3) yes C29 C28 C30 121.4(2) yes C24 C29 C28 121.7(2) yes C24 C29 H291 118.9 no C28 C29 H291 119.4 no C28 C30 N39 113.7(2) yes C28 C30 H301 108.4 no N39 C30 H301 110.3 no C28 C30 H302 109.7 no N39 C30 H302 107.5 no H301 C30 H302 107.0 no C32 C31 C33 111.6(2) yes C32 C31 N39 112.3(2) yes C33 C31 N39 111.4(2) yes C32 C31 H311 106.0 no C33 C31 H311 108.1 no N39 C31 H311 107.2 no C31 C32 H321 110.6 no C31 C32 H322 108.8 no H321 C32 H322 110.9 no C31 C32 H323 108.6 no H321 C32 H323 109.9 no H322 C32 H323 108.0 no C31 C33 H331 105.0 no C31 C33 H332 108.0 no H331 C33 H332 112.1 no C31 C33 H333 109.3 no H331 C33 H333 107.5 no H332 C33 H333 114.6 no C8 N37 C9 118.6(2) yes C8 N37 C12 116.8(2) yes C9 N37 C12 123.63(18) yes C20 N38 C19 117.81(19) yes C20 N38 C23 122.9(2) yes C19 N38 C23 118.6(2) yes C30 N39 C31 118.41(19) yes C30 N39 C1 115.57(19) yes C31 N39 C1 122.54(19) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.502(3) yes C1 O34 1.221(3) yes C1 N39 1.354(3) yes C2 C3 1.378(3) yes C2 C7 1.386(3) yes C3 C4 1.374(4) yes C3 H31 0.973 no C4 C5 1.367(4) yes C4 H41 0.981 no C5 C6 1.388(3) yes C5 H51 0.960 no C6 C7 1.380(3) yes C6 C8 1.494(3) yes C7 H71 0.971 no C8 N37 1.475(3) yes C8 H81 0.980 no C8 H82 0.984 no C9 C10 1.519(4) yes C9 C11 1.523(4) yes C9 N37 1.472(3) yes C9 H91 0.988 no C10 H101 0.957 no C10 H102 0.957 no C10 H103 0.958 no C11 H111 0.955 no C11 H112 0.968 no C11 H113 0.960 no C12 C13 1.491(3) yes C12 O35 1.231(3) yes C12 N37 1.339(3) yes C13 C14 1.384(3) yes C13 C18 1.380(3) yes C14 C15 1.390(4) yes C14 H141 1.007 no C15 C16 1.368(4) yes C15 H151 0.963 no C16 C17 1.376(3) yes C16 H161 0.967 no C17 C18 1.397(3) yes C17 C19 1.507(3) yes C18 H181 0.980 no C19 N38 1.455(3) yes C19 H191 0.988 no C19 H192 1.012 no C20 C21 1.521(4) yes C20 C22 1.518(4) yes C20 N38 1.473(3) yes C20 H201 1.038 no C21 H211 0.967 no C21 H212 0.953 no C21 H213 0.985 no C22 H221 0.967 no C22 H222 0.965 no C22 H223 0.980 no C23 C24 1.493(4) yes C23 O36 1.232(3) yes C23 N38 1.344(3) yes C24 C25 1.380(4) yes C24 C29 1.393(3) yes C25 C26 1.364(4) yes C25 H251 0.976 no C26 C27 1.380(4) yes C26 H261 0.988 no C27 C28 1.390(3) yes C27 H271 0.962 no C28 C29 1.382(3) yes C28 C30 1.503(3) yes C29 H291 0.967 no C30 N39 1.476(3) yes C30 H301 1.021 no C30 H302 0.999 no C31 C32 1.516(3) yes C31 C33 1.519(4) yes C31 N39 1.464(3) yes C31 H311 1.012 no C32 H321 0.978 no C32 H322 0.962 no C32 H323 0.969 no C33 H331 0.962 no C33 H332 0.962 no C33 H333 0.963 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 C19 H192 O35 3_545 152.39(8) 1.012 2.347 3.277(4) yes C20 H201 C29 . 122.27(8) 1.038 2.589 3.263(4) yes C21 H212 O36 1_455 144.27(9) 0.953 2.523 3.344(4) yes loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag -1 -2 3 x 0 3 2 x 0 0 6 x 0 3 4 x 0 -3 4 x 0 3 5 x 0 3 3 x 0 4 3 x 0 -4 3 x 0 3 6 x 0 -3 6 x