# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Duncan Bruce' 'Wyeth Callaway' 'Richard W. Date' 'Stephen P Dudek' 'Vincent Lynch' 'Jonathan L. Sessler' _publ_contact_author_name 'Prof Duncan Bruce' _publ_contact_author_address ; Prof Duncan Bruce School of Chemistry University of Exeter Stocker Road Exeter EX4 4QD UNITED KINGDOM ; _publ_contact_author_email D.BRUCE@EXETER.AC.UK _publ_section_title ; The First Liquid-crystalline, Expanded Porphyrins ; data_aza _database_code_CSD 216305 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H44 N12 O10' _chemical_formula_weight 780.82 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.4409(1) _cell_length_b 13.4669(2) _cell_length_c 19.1745(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.1340(8) _cell_angle_gamma 90.00 _cell_volume 1921.39(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'long needles' _exptl_crystal_colour black _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8262 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4363 _reflns_number_gt 3055 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+1.0354P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0101(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4363 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1008 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1528 _refine_ls_wR_factor_gt 0.1412 _refine_ls_goodness_of_fit_ref 1.333 _refine_ls_restrained_S_all 1.333 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.003 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.2719(3) 0.62177(15) 0.73359(11) 0.0318(5) Uani 1 1 d . . . C2 C 0.2834(3) 0.66965(17) 0.79608(12) 0.0330(5) Uani 1 1 d . . . C3 C 0.1324(3) 0.64288(17) 0.83520(12) 0.0330(5) Uani 1 1 d . . . C4 C 0.0292(3) 0.57847(18) 0.79460(13) 0.0334(6) Uani 1 1 d . . . C5 C 0.1179(3) 0.56578(17) 0.73087(12) 0.0310(5) Uani 1 1 d . . . C6 C 0.0627(3) 0.50435(17) 0.67476(12) 0.0315(5) Uani 1 1 d . . . H6 H -0.0491 0.4692 0.6787 0.038 Uiso 1 1 d R . . N7 N 0.1555(3) 0.49390(14) 0.61832(10) 0.0313(5) Uani 1 1 d . . . N8 N 0.0778(3) 0.42603(15) 0.57175(10) 0.0323(5) Uani 1 1 d . . . C9 C 0.1758(3) 0.41142(17) 0.51755(12) 0.0305(5) Uani 1 1 d . . . H9 H 0.2842 0.4494 0.5126 0.037 Uiso 1 1 d R . . C10 C 0.1295(3) 0.34075(17) 0.46438(11) 0.0286(5) Uani 1 1 d . . . N11 N 0.2373(3) 0.33241(16) 0.40727(10) 0.0325(5) Uani 1 1 d . . . C12 C 0.1766(3) 0.25841(19) 0.36512(12) 0.0353(6) Uani 1 1 d . . . C13 C 0.0248(3) 0.21646(18) 0.39693(12) 0.0337(6) Uani 1 1 d . . . C14 C -0.0045(3) 0.26749(17) 0.45891(11) 0.0290(5) Uani 1 1 d . . . C15 C 0.2550(4) 0.2310(2) 0.30018(14) 0.0421(6) Uani 1 1 d . . . H15 H 0.1965 0.1805 0.2731 0.051 Uiso 1 1 d R . . N16 N 0.4024(3) 0.27128(16) 0.27468(11) 0.0382(5) Uani 1 1 d . . . N17 N 0.4368(3) 0.22939(18) 0.21007(12) 0.0495(6) Uani 1 1 d . . . C18 C 0.5806(4) 0.2620(2) 0.18147(15) 0.0432(6) Uani 1 1 d . . . H18 H 0.6009 0.2357 0.1356 0.052 Uiso 1 1 d R . . O19 O 0.0977(2) 0.67859(13) 0.90095(9) 0.0427(5) Uani 1 1 d . . . C20 C 0.1788(4) 0.6211(2) 0.95558(14) 0.0549(8) Uani 1 1 d . . . H20A H 0.1491 0.6495 1.0000 0.082 Uiso 1 1 d R . . H20B H 0.1362 0.5539 0.9536 0.082 Uiso 1 1 d R . . H20C H 0.3068 0.6219 0.9495 0.082 Uiso 1 1 d R . . O21 O -0.1261(2) 0.52892(15) 0.80818(10) 0.0511(5) Uani 1 1 d . . . C22 C -0.2304(4) 0.5587(3) 0.86585(15) 0.0564(8) Uani 1 1 d . . . H22A H -0.3354 0.5175 0.8687 0.085 Uiso 1 1 d R . . H22B H -0.1607 0.5517 0.9078 0.085 Uiso 1 1 d R . . H22C H -0.2660 0.6268 0.8604 0.085 Uiso 1 1 d R . . O23 O -0.1310(2) 0.24245(12) 0.50777(8) 0.0339(4) Uani 1 1 d . . . C24 C -0.2750(3) 0.3132(2) 0.51496(14) 0.0417(6) Uani 1 1 d . . . H24A H -0.3574 0.2908 0.5500 0.063 Uiso 1 1 d R . . H24B H -0.2264 0.3765 0.5283 0.063 Uiso 1 1 d R . . H24C H -0.3370 0.3196 0.4712 0.063 Uiso 1 1 d R . . O25 O -0.0615(2) 0.13514(14) 0.37130(10) 0.0486(5) Uani 1 1 d . . . C26 C -0.2509(4) 0.1423(2) 0.36766(19) 0.0666(9) Uani 1 1 d . . . H26C H -0.2930 0.2072 0.3801 0.100 Uiso 1 1 d R . . H26A H -0.2985 0.0919 0.3979 0.100 Uiso 1 1 d R . . H26B H -0.2853 0.1246 0.3210 0.100 Uiso 1 1 d R . . O1A O 0.5151(3) 0.51970(14) 0.61979(9) 0.0408(5) Uani 1 1 d . . . C2A C 0.5585(4) 0.4460(2) 0.67104(15) 0.0487(7) Uani 1 1 d . . . H2AC H 0.4752 0.4521 0.7090 0.073 Uiso 1 1 d R . . H2AA H 0.6779 0.4552 0.6890 0.073 Uiso 1 1 d R . . H2AB H 0.5483 0.3803 0.6520 0.073 Uiso 1 1 d R . . H11 H 0.327(4) 0.376(2) 0.3972(14) 0.044(8) Uiso 1 1 d . . . H1 H 0.345(4) 0.622(2) 0.7026(14) 0.041(8) Uiso 1 1 d . . . H1A H 0.400(4) 0.520(2) 0.6143(16) 0.061(10) Uiso 1 1 d . . . 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 0.0310(11) 0.0321(11) 0.0322(11) -0.0022(9) 0.0069(9) -0.0014(9) C2 0.0338(12) 0.0285(12) 0.0367(13) -0.0052(10) 0.0042(10) 0.0008(10) C3 0.0346(13) 0.0283(12) 0.0360(13) -0.0036(10) 0.0049(10) 0.0028(10) C4 0.0296(12) 0.0317(13) 0.0389(14) 0.0007(11) 0.0044(10) 0.0003(10) C5 0.0288(12) 0.0290(12) 0.0351(13) 0.0019(10) -0.0010(10) -0.0003(10) C6 0.0287(12) 0.0327(13) 0.0333(13) 0.0034(10) -0.0025(10) -0.0007(10) N7 0.0328(10) 0.0296(11) 0.0314(10) -0.0005(8) -0.0078(9) -0.0017(8) N8 0.0348(11) 0.0347(11) 0.0274(10) 0.0015(9) -0.0051(9) -0.0040(9) C9 0.0307(12) 0.0280(12) 0.0329(13) 0.0056(10) -0.0080(10) -0.0023(10) C10 0.0273(11) 0.0315(12) 0.0269(12) 0.0041(10) -0.0017(9) -0.0004(9) N11 0.0290(10) 0.0356(12) 0.0329(11) 0.0015(9) 0.0010(9) -0.0036(9) C12 0.0319(12) 0.0402(14) 0.0338(13) -0.0011(11) 0.0046(10) 0.0004(11) C13 0.0348(13) 0.0325(13) 0.0339(13) -0.0031(10) 0.0010(10) -0.0029(10) C14 0.0290(11) 0.0298(12) 0.0283(12) 0.0039(10) 0.0015(9) 0.0002(10) C15 0.0434(15) 0.0432(15) 0.0398(14) -0.0091(12) 0.0051(12) -0.0045(12) N16 0.0381(12) 0.0382(12) 0.0382(12) -0.0115(10) 0.0005(9) -0.0057(10) N17 0.0521(14) 0.0548(15) 0.0417(13) -0.0183(11) 0.0100(11) -0.0117(12) C18 0.0425(15) 0.0427(15) 0.0443(15) -0.0087(12) 0.0078(12) -0.0094(12) O19 0.0478(10) 0.0436(11) 0.0368(10) -0.0108(8) 0.0117(8) 0.0003(8) C20 0.0625(19) 0.066(2) 0.0359(15) -0.0073(14) -0.0018(13) -0.0086(16) O21 0.0396(10) 0.0554(12) 0.0585(12) -0.0142(10) 0.0166(9) -0.0169(9) C22 0.0360(15) 0.080(2) 0.0533(18) -0.0054(16) 0.0157(13) -0.0093(15) O23 0.0374(9) 0.0336(9) 0.0309(9) 0.0047(7) 0.0085(7) -0.0036(7) C24 0.0357(14) 0.0432(15) 0.0462(15) 0.0010(12) 0.0118(12) -0.0044(12) O25 0.0475(11) 0.0433(11) 0.0551(12) -0.0176(9) 0.0040(9) -0.0116(9) C26 0.060(2) 0.0481(18) 0.091(3) -0.0071(18) -0.0264(18) -0.0171(15) O1A 0.0332(10) 0.0489(11) 0.0402(10) 0.0030(8) -0.0012(8) -0.0124(9) C2A 0.0394(15) 0.0564(18) 0.0504(17) 0.0067(14) -0.0026(13) 0.0065(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.363(3) . ? N1 C5 1.372(3) . ? N1 H1 0.80(3) . ? C2 C3 1.400(3) . ? C2 C18 1.433(3) 3_666 ? C3 O19 1.374(3) . ? C3 C4 1.395(3) . ? C4 O21 1.360(3) . ? C4 C5 1.401(3) . ? C5 C6 1.417(3) . ? C6 N7 1.293(3) . ? C6 H6 0.9600 . ? N7 N8 1.402(3) . ? N8 C9 1.286(3) . ? C9 C10 1.436(3) . ? C9 H9 0.9600 . ? C10 N11 1.364(3) . ? C10 C14 1.406(3) . ? N11 C12 1.360(3) . ? N11 H11 0.91(3) . ? C12 C13 1.403(3) . ? C12 C15 1.425(3) . ? C13 O25 1.361(3) . ? C13 C14 1.391(3) . ? C14 O23 1.372(3) . ? C15 N16 1.318(3) . ? C15 H15 0.9599 . ? N16 N17 1.386(3) . ? N17 C18 1.281(3) . ? C18 C2 1.433(3) 3_666 ? C18 H18 0.9600 . ? O19 C20 1.434(3) . ? C20 H20A 0.9599 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? O21 C22 1.410(3) . ? C22 H22A 0.9599 . ? C22 H22B 0.9599 . ? C22 H22C 0.9601 . ? O23 C24 1.441(3) . ? C24 H24A 0.9601 . ? C24 H24B 0.9599 . ? C24 H24C 0.9600 . ? O25 C26 1.414(4) . ? C26 H26C 0.9599 . ? C26 H26A 0.9600 . ? C26 H26B 0.9601 . ? O1A C2A 1.433(3) . ? O1A H1A 0.86(3) . ? C2A H2AC 0.9600 . ? C2A H2AA 0.9600 . ? C2A H2AB 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 110.1(2) . . ? C2 N1 H1 127(2) . . ? C5 N1 H1 123(2) . . ? N1 C2 C3 107.5(2) . . ? N1 C2 C18 127.6(2) . 3_666 ? C3 C2 C18 124.9(2) . 3_666 ? O19 C3 C4 128.7(2) . . ? O19 C3 C2 123.7(2) . . ? C4 C3 C2 107.6(2) . . ? O21 C4 C3 131.7(2) . . ? O21 C4 C5 120.6(2) . . ? C3 C4 C5 107.6(2) . . ? N1 C5 C4 107.2(2) . . ? N1 C5 C6 126.2(2) . . ? C4 C5 C6 126.6(2) . . ? N7 C6 C5 123.0(2) . . ? N7 C6 H6 118.5 . . ? C5 C6 H6 118.5 . . ? C6 N7 N8 112.57(19) . . ? C9 N8 N7 112.39(19) . . ? N8 C9 C10 122.7(2) . . ? N8 C9 H9 118.5 . . ? C10 C9 H9 118.8 . . ? N11 C10 C14 107.5(2) . . ? N11 C10 C9 118.9(2) . . ? C14 C10 C9 133.4(2) . . ? C12 N11 C10 110.0(2) . . ? C12 N11 H11 126.3(17) . . ? C10 N11 H11 123.3(17) . . ? N11 C12 C13 107.7(2) . . ? N11 C12 C15 124.9(2) . . ? C13 C12 C15 127.4(2) . . ? O25 C13 C14 129.1(2) . . ? O25 C13 C12 123.1(2) . . ? C14 C13 C12 107.5(2) . . ? O23 C14 C13 124.9(2) . . ? O23 C14 C10 127.5(2) . . ? C13 C14 C10 107.3(2) . . ? N16 C15 C12 124.1(2) . . ? N16 C15 H15 117.8 . . ? C12 C15 H15 118.1 . . ? C15 N16 N17 108.7(2) . . ? C18 N17 N16 113.5(2) . . ? N17 C18 C2 133.0(3) . 3_666 ? N17 C18 H18 113.5 . . ? C2 C18 H18 113.6 3_666 . ? C3 O19 C20 113.7(2) . . ? O19 C20 H20A 109.6 . . ? O19 C20 H20B 110.0 . . ? H20A C20 H20B 109.5 . . ? O19 C20 H20C 108.8 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C4 O21 C22 118.7(2) . . ? O21 C22 H22A 109.2 . . ? O21 C22 H22B 109.4 . . ? H22A C22 H22B 109.5 . . ? O21 C22 H22C 109.8 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C14 O23 C24 114.49(17) . . ? O23 C24 H24A 109.6 . . ? O23 C24 H24B 109.4 . . ? H24A C24 H24B 109.5 . . ? O23 C24 H24C 109.4 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C13 O25 C26 115.7(2) . . ? O25 C26 H26C 112.1 . . ? O25 C26 H26A 107.0 . . ? H26C C26 H26A 111.8 . . ? O25 C26 H26B 107.0 . . ? H26C C26 H26B 111.8 . . ? H26A C26 H26B 106.8 . . ? C2A O1A H1A 108(2) . . ? O1A C2A H2AC 108.4 . . ? O1A C2A H2AA 111.3 . . ? H2AC C2A H2AA 108.4 . . ? O1A C2A H2AB 111.2 . . ? H2AC C2A H2AB 108.4 . . ? H2AA C2A H2AB 109.1 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C2 C3 0.5(3) . . . . ? C5 N1 C2 C18 -177.5(2) . . . 3_666 ? N1 C2 C3 O19 -178.9(2) . . . . ? C18 C2 C3 O19 -0.8(4) 3_666 . . . ? N1 C2 C3 C4 -0.5(3) . . . . ? C18 C2 C3 C4 177.6(2) 3_666 . . . ? O19 C3 C4 O21 -3.9(4) . . . . ? C2 C3 C4 O21 177.8(3) . . . . ? O19 C3 C4 C5 178.6(2) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? C2 N1 C5 C4 -0.4(3) . . . . ? C2 N1 C5 C6 -178.6(2) . . . . ? O21 C4 C5 N1 -177.8(2) . . . . ? C3 C4 C5 N1 0.1(3) . . . . ? O21 C4 C5 C6 0.4(4) . . . . ? C3 C4 C5 C6 178.3(2) . . . . ? N1 C5 C6 N7 0.4(4) . . . . ? C4 C5 C6 N7 -177.5(2) . . . . ? C5 C6 N7 N8 177.3(2) . . . . ? C6 N7 N8 C9 -176.2(2) . . . . ? N7 N8 C9 C10 176.33(19) . . . . ? N8 C9 C10 N11 177.6(2) . . . . ? N8 C9 C10 C14 -8.0(4) . . . . ? C14 C10 N11 C12 1.0(3) . . . . ? C9 C10 N11 C12 176.8(2) . . . . ? C10 N11 C12 C13 -0.9(3) . . . . ? C10 N11 C12 C15 178.5(2) . . . . ? N11 C12 C13 O25 -174.7(2) . . . . ? C15 C12 C13 O25 5.9(4) . . . . ? N11 C12 C13 C14 0.4(3) . . . . ? C15 C12 C13 C14 -179.0(2) . . . . ? O25 C13 C14 O23 0.8(4) . . . . ? C12 C13 C14 O23 -173.9(2) . . . . ? O25 C13 C14 C10 175.0(2) . . . . ? C12 C13 C14 C10 0.3(3) . . . . ? N11 C10 C14 O23 173.2(2) . . . . ? C9 C10 C14 O23 -1.7(4) . . . . ? N11 C10 C14 C13 -0.8(3) . . . . ? C9 C10 C14 C13 -175.6(2) . . . . ? N11 C12 C15 N16 3.6(4) . . . . ? C13 C12 C15 N16 -177.2(3) . . . . ? C12 C15 N16 N17 -178.2(3) . . . . ? C15 N16 N17 C18 -178.4(3) . . . . ? N16 N17 C18 C2 2.7(5) . . . 3_666 ? C4 C3 O19 C20 94.1(3) . . . . ? C2 C3 O19 C20 -87.8(3) . . . . ? C3 C4 O21 C22 15.8(4) . . . . ? C5 C4 O21 C22 -166.9(2) . . . . ? C13 C14 O23 C24 -112.9(3) . . . . ? C10 C14 O23 C24 74.2(3) . . . . ? C14 C13 O25 C26 52.8(4) . . . . ? C12 C13 O25 C26 -133.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 O1A 0.91(3) 1.86(3) 2.763(3) 171(3) 3_666 N1 H1 N16 0.80(3) 2.40(3) 2.824(3) 114(2) 3_666 O1A H1A N7 0.86(3) 1.86(3) 2.698(3) 166(3) . N1 H1 O1A 0.80(3) 2.46(3) 3.153(3) 145(3) . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.644 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.062