# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2005 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Dr Pierre Audebert' _publ_contact_author_address ; PPSM ENS Cachan 61 Blvd du President Wilson Cachan 94235 FRANCE ; _publ_contact_author_email AUDEBERT@PPSM.ENS-CACHAN.FR _publ_section_title ; Electrochromic Conjugated N-Salicylidene-Aniline (Anil) Functionalized Pyrrole and 2,5-Dithienylpyrrole-Based Polymers ; loop_ _publ_author_name 'P. Audebert' 'Khalil Abboud' 'Keitaro Nakatani' 'J. Reynolds' 'Barry C. Thompson' data_bct1 _database_code_depnum_ccdc_archive 'CCDC 268887' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H30 N2 O' _chemical_formula_weight 374.51 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8773(6) _cell_length_b 12.1540(7) _cell_length_c 18.6430(11) _cell_angle_alpha 100.878(2) _cell_angle_beta 93.328(2) _cell_angle_gamma 94.944(2) _cell_volume 2183.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 37 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.0 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.139 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9844 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details 'based on measured indexed crystal faces, SHELXTL (Bruker 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 16332 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7625 _reflns_number_gt 4710 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker 1998)' _computing_cell_refinement 'Bruker SMART & SAINT (Bruker 1998)' _computing_data_reduction 'Bruker SHELXTL (Bruker 2000)' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0588P)^2^+0.2871P] 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 0.0013(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7625 _refine_ls_number_parameters 581 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 O1 O 0.47263(15) 0.51562(14) 0.20698(10) 0.0530(4) Uani 1 1 d . . . H1 H 0.502(3) 0.582(2) 0.2454(15) 0.084(9) Uiso 1 1 d . . . N1 N 0.78187(17) 1.04673(14) 0.50789(9) 0.0399(4) Uani 1 1 d . . . N2 N 0.47894(18) 0.69580(15) 0.30730(10) 0.0462(5) Uani 1 1 d . . . C1 C 0.7938(2) 1.15870(19) 0.50523(13) 0.0468(6) Uani 1 1 d . . . H1A H 0.7523 1.1918 0.4684 0.056 Uiso 1 1 calc R . . C2 C 0.8752(2) 1.2145(2) 0.56445(13) 0.0505(6) Uani 1 1 d . . . H2A H 0.9011 1.2933 0.5761 0.061 Uiso 1 1 calc R . . C3 C 0.9144(2) 1.1350(2) 0.60534(13) 0.0525(6) Uani 1 1 d . . . H3A H 0.9705 1.1500 0.6499 0.063 Uiso 1 1 calc R . . C4 C 0.8568(2) 1.0326(2) 0.56904(13) 0.0495(6) Uani 1 1 d . . . H4A H 0.8669 0.9628 0.5837 0.059 Uiso 1 1 calc R . . C5 C 0.7041(2) 0.95943(18) 0.45652(12) 0.0387(5) Uani 1 1 d . . . C6 C 0.5844(2) 0.98027(19) 0.42086(12) 0.0455(6) Uani 1 1 d . . . H6A H 0.5543 1.0534 0.4305 0.055 Uiso 1 1 calc R . . C7 C 0.5090(2) 0.89497(19) 0.37141(12) 0.0482(6) Uani 1 1 d . . . H7A H 0.4276 0.9101 0.3470 0.058 Uiso 1 1 calc R . . C8 C 0.5508(2) 0.78757(19) 0.35698(12) 0.0413(5) Uani 1 1 d . . . C9 C 0.6710(2) 0.76817(19) 0.39230(12) 0.0459(6) Uani 1 1 d . . . H9A H 0.7015 0.6952 0.3823 0.055 Uiso 1 1 calc R . . C10 C 0.7474(2) 0.85255(18) 0.44167(12) 0.0431(6) Uani 1 1 d . . . H10A H 0.8295 0.8375 0.4655 0.052 Uiso 1 1 calc R . . C11 C 0.3492(2) 0.68965(19) 0.29532(12) 0.0448(6) Uani 1 1 d . . . H11A H 0.3017 0.7472 0.3215 0.054 Uiso 1 1 calc R . . C12 C 0.2718(2) 0.59909(19) 0.24374(12) 0.0419(5) Uani 1 1 d . . . C13 C 0.1294(2) 0.5975(2) 0.23733(12) 0.0456(6) Uani 1 1 d . . . H13A H 0.0872 0.6550 0.2672 0.055 Uiso 1 1 calc R . . C14 C 0.0497(2) 0.51490(19) 0.18885(12) 0.0439(6) Uani 1 1 d . . . C15 C 0.1170(2) 0.43323(19) 0.14470(12) 0.0440(6) Uani 1 1 d . . . H15A H 0.0631 0.3766 0.1102 0.053 Uiso 1 1 calc R . . C16 C 0.2577(2) 0.42996(18) 0.14831(11) 0.0397(5) Uani 1 1 d . . . C17 C 0.3349(2) 0.51440(18) 0.20004(12) 0.0401(5) Uani 1 1 d . . . C18 C 0.3257(2) 0.33997(19) 0.09804(13) 0.0494(6) Uani 1 1 d . . . C19 C 0.4061(3) 0.2711(2) 0.14387(15) 0.0673(8) Uani 1 1 d . . . H19C H 0.3439 0.2348 0.1734 0.101 Uiso 1 1 calc R . . H19B H 0.4767 0.3212 0.1762 0.101 Uiso 1 1 calc R . . H19A H 0.4488 0.2135 0.1112 0.101 Uiso 1 1 calc R . . C20 C 0.2216(3) 0.2569(2) 0.04643(15) 0.0705(8) Uani 1 1 d . . . H20C H 0.1630 0.2158 0.0752 0.106 Uiso 1 1 calc R . . H20B H 0.2694 0.2035 0.0133 0.106 Uiso 1 1 calc R . . H20A H 0.1656 0.2983 0.0177 0.106 Uiso 1 1 calc R . . C21 C 0.4207(3) 0.3974(2) 0.05080(14) 0.0675(8) Uani 1 1 d . . . H21C H 0.4627 0.3400 0.0174 0.101 Uiso 1 1 calc R . . H21B H 0.4921 0.4476 0.0825 0.101 Uiso 1 1 calc R . . H21A H 0.3680 0.4413 0.0223 0.101 Uiso 1 1 calc R . . C22 C -0.1061(2) 0.5104(2) 0.18111(14) 0.0565(7) Uani 1 1 d . . . C23 C -0.1591(3) 0.5890(3) 0.24492(19) 0.0986(12) Uani 1 1 d . . . H23C H -0.1364 0.6674 0.2403 0.148 Uiso 1 1 calc R . . H23B H -0.1167 0.5768 0.2912 0.148 Uiso 1 1 calc R . . H23A H -0.2583 0.5734 0.2442 0.148 Uiso 1 1 calc R . . C24 C -0.1710(3) 0.3917(2) 0.18181(17) 0.0790(9) Uani 1 1 d . . . H24C H -0.2704 0.3912 0.1792 0.119 Uiso 1 1 calc R . . H24B H -0.1396 0.3688 0.2271 0.119 Uiso 1 1 calc R . . H24A H -0.1444 0.3391 0.1396 0.119 Uiso 1 1 calc R . . C25 C -0.1502(3) 0.5426(3) 0.10862(16) 0.0844(10) Uani 1 1 d . . . H25C H -0.2499 0.5373 0.1026 0.127 Uiso 1 1 calc R . . H25B H -0.1162 0.4911 0.0681 0.127 Uiso 1 1 calc R . . H25A H -0.1127 0.6199 0.1086 0.127 Uiso 1 1 calc R . . O2 O 0.43751(16) 1.01686(16) 0.20703(10) 0.0473(6) Uani 0.902(4) 1 d P A 3 H2 H 0.470(3) 1.083(3) 0.248(2) 0.101(12) Uiso 0.902(4) 1 d P A 3 O2' O 0.1089(15) 1.1434(12) 0.3119(8) 0.039(5) Uani 0.098(4) 1 d P A 4 H2' H 0.0645 1.1961 0.3036 0.058 Uiso 0.098(4) 1 calc PR A 4 N3 N 0.77472(18) 1.51346(14) 0.52618(10) 0.0425(5) Uani 1 1 d . . . N4 N 0.4531(2) 1.1826(2) 0.31867(12) 0.0414(6) Uani 0.902(4) 1 d P A 3 N4' N 0.374(2) 1.203(2) 0.3523(14) 0.050(7) Uani 0.098(4) 1 d P A 4 C26 C 0.8671(2) 1.59491(19) 0.51027(14) 0.0490(6) Uani 1 1 d . . . H26A H 0.8819 1.6083 0.4626 0.059 Uiso 1 1 calc R . . C27 C 0.9338(2) 1.6530(2) 0.57340(14) 0.0532(6) Uani 1 1 d . . . H27A H 1.0026 1.7141 0.5781 0.064 Uiso 1 1 calc R . . C28 C 0.8821(3) 1.60580(19) 0.63076(14) 0.0561(7) Uani 1 1 d . . . H28A H 0.9100 1.6289 0.6814 0.067 Uiso 1 1 calc R . . C29 C 0.7849(3) 1.5213(2) 0.60051(13) 0.0555(7) Uani 1 1 d . . . H29A H 0.7326 1.4751 0.6267 0.067 Uiso 1 1 calc R . . C30 C 0.6883(2) 1.43276(18) 0.47494(12) 0.0416(6) Uani 1 1 d . A . C31 C 0.7214(2) 1.40408(19) 0.40275(13) 0.0500(6) Uani 1 1 d . . . H31A H 0.8006 1.4406 0.3876 0.060 Uiso 1 1 calc R . . C32 C 0.6409(2) 1.3237(2) 0.35312(13) 0.0544(6) Uani 1 1 d . A . H32A H 0.6656 1.3051 0.3041 0.065 Uiso 1 1 calc R . . C33 C 0.5253(2) 1.26952(19) 0.37312(12) 0.0476(6) Uani 1 1 d . . . C34 C 0.4913(2) 1.29838(19) 0.44557(13) 0.0502(6) Uani 1 1 d . A . H34A H 0.4117 1.2618 0.4604 0.060 Uiso 1 1 calc R . . C35 C 0.5720(2) 1.37963(18) 0.49612(12) 0.0465(6) Uani 1 1 d . . . H35A H 0.5475 1.3987 0.5451 0.056 Uiso 1 1 calc R A . C36 C 0.3230(3) 1.1682(3) 0.31831(18) 0.0397(7) Uani 0.902(4) 1 d P A 3 H36A H 0.2779 1.2141 0.3546 0.048 Uiso 0.902(4) 1 calc PR A 3 C36' C 0.387(3) 1.122(2) 0.3011(12) 0.030(6) Uiso 0.098(4) 1 d P A 4 H36B H 0.4698 1.0920 0.2881 0.036 Uiso 0.098(4) 1 calc PR A 4 C37 C 0.2424(2) 1.08188(19) 0.26281(12) 0.0466(6) Uani 1 1 d . . . C38 C 0.3014(2) 1.0099(2) 0.20806(13) 0.0468(6) Uani 1 1 d . A . H38A H 0.3979 1.0126 0.2081 0.056 Uiso 0.098(4) 1 calc PR A 4 C39 C 0.2189(2) 0.93333(19) 0.15271(12) 0.0461(6) Uani 1 1 d . . . C40 C 0.0788(2) 0.93366(19) 0.15690(12) 0.0470(6) Uani 1 1 d . A . H40A H 0.0211 0.8824 0.1208 0.056 Uiso 1 1 calc R . . C41 C 0.0168(2) 1.00496(19) 0.21116(12) 0.0447(6) Uani 1 1 d . . . C42 C 0.1019(2) 1.0780(2) 0.26348(14) 0.0457(6) Uani 1 1 d . A . H42A H 0.0633 1.1269 0.3010 0.055 Uiso 0.902(4) 1 calc PR A 3 C43 C -0.1384(2) 1.0038(2) 0.20947(14) 0.0526(6) Uani 1 1 d . A . C44' C -0.1880(4) 1.0807(4) 0.2772(2) 0.0674(13) Uani 0.738(5) 1 d P A 1 H44F H -0.2878 1.0743 0.2739 0.101 Uiso 0.738(5) 1 calc PR A 1 H44E H -0.1529 1.1590 0.2785 0.101 Uiso 0.738(5) 1 calc PR A 1 H44D H -0.1544 1.0573 0.3220 0.101 Uiso 0.738(5) 1 calc PR A 1 C44 C -0.1795(12) 0.9896(13) 0.2778(7) 0.080(4) Uani 0.262(5) 1 d P A 2 H44C H -0.2750 1.0047 0.2813 0.120 Uiso 0.262(5) 1 calc PR A 2 H44B H -0.1224 1.0420 0.3165 0.120 Uiso 0.262(5) 1 calc PR A 2 H44A H -0.1699 0.9121 0.2836 0.120 Uiso 0.262(5) 1 calc PR A 2 C45' C -0.2052(3) 0.8825(3) 0.2109(2) 0.0678(14) Uani 0.738(5) 1 d P A 1 H45F H -0.1728 0.8597 0.2560 0.102 Uiso 0.738(5) 1 calc PR A 1 H45E H -0.1801 0.8296 0.1684 0.102 Uiso 0.738(5) 1 calc PR A 1 H45D H -0.3046 0.8826 0.2091 0.102 Uiso 0.738(5) 1 calc PR A 1 C45 C -0.2025(10) 0.9226(10) 0.1423(6) 0.072(4) Uani 0.262(5) 1 d P A 2 H45C H -0.1893 0.8454 0.1474 0.108 Uiso 0.262(5) 1 calc PR A 2 H45B H -0.1595 0.9390 0.0989 0.108 Uiso 0.262(5) 1 calc PR A 2 H45A H -0.3002 0.9307 0.1369 0.108 Uiso 0.262(5) 1 calc PR A 2 C46' C -0.1961(4) 1.0381(4) 0.1408(2) 0.0697(14) Uani 0.738(5) 1 d P A 1 H46F H -0.2957 1.0342 0.1405 0.105 Uiso 0.738(5) 1 calc PR A 1 H46E H -0.1707 0.9870 0.0975 0.105 Uiso 0.738(5) 1 calc PR A 1 H46D H -0.1594 1.1153 0.1398 0.105 Uiso 0.738(5) 1 calc PR A 1 C46 C -0.1533(14) 1.1270(10) 0.1929(8) 0.090(5) Uani 0.262(5) 1 d P A 2 H46C H -0.2496 1.1350 0.1812 0.136 Uiso 0.262(5) 1 calc PR A 2 H46B H -0.1011 1.1377 0.1512 0.136 Uiso 0.262(5) 1 calc PR A 2 H46A H -0.1183 1.1838 0.2361 0.136 Uiso 0.262(5) 1 calc PR A 2 C47 C 0.2799(2) 0.8569(2) 0.09020(13) 0.0543(6) Uani 1 1 d . A . C48 C 0.1716(3) 0.7818(3) 0.03834(17) 0.1017(12) Uani 1 1 d . . . H48C H 0.2148 0.7385 -0.0024 0.153 Uiso 1 1 calc R A . H48B H 0.1073 0.8282 0.0192 0.153 Uiso 1 1 calc R . . H48A H 0.1228 0.7300 0.0646 0.153 Uiso 1 1 calc R . . C49 C 0.3747(3) 0.7811(2) 0.12158(16) 0.0788(9) Uani 1 1 d . . . H49C H 0.3219 0.7318 0.1480 0.118 Uiso 1 1 calc R A . H49B H 0.4460 0.8279 0.1553 0.118 Uiso 1 1 calc R . . H49A H 0.4166 0.7351 0.0815 0.118 Uiso 1 1 calc R . . C50 C 0.3620(3) 0.9296(2) 0.04577(14) 0.0707(8) Uani 1 1 d . . . H50C H 0.3965 0.8809 0.0042 0.106 Uiso 1 1 calc R A . H50B H 0.4387 0.9734 0.0771 0.106 Uiso 1 1 calc R . . H50A H 0.3031 0.9810 0.0277 0.106 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 0.0334(9) 0.0575(11) 0.0629(11) 0.0011(9) -0.0007(8) 0.0023(8) N1 0.0356(10) 0.0411(11) 0.0420(11) 0.0087(9) -0.0005(8) -0.0007(8) N2 0.0378(11) 0.0531(12) 0.0452(12) 0.0081(10) -0.0020(9) -0.0022(9) C1 0.0442(14) 0.0455(14) 0.0518(15) 0.0153(12) 0.0014(11) 0.0004(11) C2 0.0447(14) 0.0442(14) 0.0581(16) 0.0026(12) 0.0046(12) -0.0040(11) C3 0.0398(14) 0.0603(16) 0.0522(15) 0.0009(13) -0.0059(11) 0.0044(12) C4 0.0467(14) 0.0532(15) 0.0479(15) 0.0118(12) -0.0090(11) 0.0052(12) C5 0.0329(12) 0.0425(13) 0.0410(13) 0.0113(11) 0.0024(10) -0.0008(10) C6 0.0409(13) 0.0396(13) 0.0573(15) 0.0143(12) -0.0022(11) 0.0038(10) C7 0.0399(13) 0.0530(15) 0.0532(15) 0.0205(12) -0.0089(11) -0.0010(11) C8 0.0372(13) 0.0455(14) 0.0402(13) 0.0083(11) 0.0020(10) -0.0019(11) C9 0.0375(13) 0.0460(14) 0.0519(15) 0.0038(12) 0.0015(11) 0.0060(11) C10 0.0328(12) 0.0506(14) 0.0450(14) 0.0076(11) -0.0019(10) 0.0063(11) C11 0.0416(14) 0.0524(14) 0.0393(13) 0.0083(11) 0.0030(11) 0.0004(11) C12 0.0382(13) 0.0485(14) 0.0377(13) 0.0109(11) -0.0006(10) -0.0054(11) C13 0.0371(13) 0.0568(15) 0.0424(14) 0.0093(12) 0.0037(10) 0.0017(11) C14 0.0371(13) 0.0518(14) 0.0418(13) 0.0105(11) -0.0010(11) -0.0022(11) C15 0.0406(13) 0.0486(14) 0.0404(13) 0.0094(11) -0.0045(10) -0.0054(11) C16 0.0380(13) 0.0447(13) 0.0378(13) 0.0138(11) 0.0010(10) -0.0006(10) C17 0.0309(12) 0.0495(14) 0.0409(13) 0.0136(11) -0.0006(10) 0.0008(10) C18 0.0460(14) 0.0472(14) 0.0536(15) 0.0076(12) -0.0014(12) 0.0055(11) C19 0.0635(17) 0.0539(16) 0.085(2) 0.0162(15) -0.0048(15) 0.0110(13) C20 0.0648(18) 0.0624(18) 0.0732(19) -0.0123(15) -0.0024(15) 0.0056(14) C21 0.0689(18) 0.0752(19) 0.0585(17) 0.0089(15) 0.0190(14) 0.0069(15) C22 0.0338(13) 0.0745(18) 0.0561(16) 0.0051(14) -0.0040(12) -0.0007(12) C23 0.0355(16) 0.133(3) 0.108(3) -0.026(2) 0.0059(16) 0.0096(17) C24 0.0439(16) 0.103(2) 0.087(2) 0.0222(18) 0.0033(14) -0.0178(16) C25 0.0492(17) 0.114(3) 0.094(2) 0.038(2) -0.0159(16) 0.0079(17) O2 0.0354(11) 0.0593(12) 0.0452(11) 0.0038(9) 0.0064(8) 0.0043(9) O2' 0.042(10) 0.029(9) 0.038(10) -0.010(7) -0.002(7) 0.009(7) N3 0.0436(11) 0.0397(11) 0.0429(11) 0.0089(9) -0.0068(9) 0.0019(9) N4 0.0346(13) 0.0487(15) 0.0396(13) 0.0069(11) 0.0013(11) 0.0021(12) N4' 0.016(13) 0.082(18) 0.047(16) 0.003(13) -0.004(11) 0.005(12) C26 0.0424(14) 0.0459(14) 0.0586(16) 0.0121(12) 0.0006(12) 0.0009(11) C27 0.0422(14) 0.0467(14) 0.0661(18) 0.0031(13) -0.0039(13) 0.0021(11) C28 0.0653(17) 0.0469(15) 0.0500(16) 0.0011(12) -0.0198(13) 0.0058(13) C29 0.0715(17) 0.0489(15) 0.0450(15) 0.0144(12) -0.0103(13) -0.0015(13) C30 0.0419(13) 0.0386(13) 0.0442(14) 0.0118(11) -0.0086(11) 0.0036(10) C31 0.0490(14) 0.0545(15) 0.0456(15) 0.0125(12) -0.0033(12) -0.0009(12) C32 0.0597(16) 0.0593(16) 0.0425(14) 0.0105(12) -0.0009(12) -0.0017(13) C33 0.0535(15) 0.0482(14) 0.0388(14) 0.0071(12) -0.0106(12) 0.0043(12) C34 0.0448(14) 0.0499(14) 0.0564(16) 0.0173(13) -0.0020(12) -0.0040(11) C35 0.0508(15) 0.0481(14) 0.0397(13) 0.0099(11) -0.0044(11) 0.0013(12) C36 0.0370(19) 0.0435(18) 0.0397(18) 0.0092(14) 0.0054(15) 0.0068(15) C37 0.0505(15) 0.0524(15) 0.0361(13) 0.0120(11) 0.0011(11) -0.0060(12) C38 0.0344(13) 0.0599(16) 0.0485(15) 0.0223(13) 0.0005(11) -0.0059(11) C39 0.0479(14) 0.0534(15) 0.0358(13) 0.0113(11) 0.0030(11) -0.0068(11) C40 0.0441(14) 0.0506(14) 0.0433(14) 0.0101(11) -0.0028(11) -0.0101(11) C41 0.0463(14) 0.0458(14) 0.0406(13) 0.0100(11) -0.0015(11) -0.0032(11) C42 0.0478(15) 0.0483(15) 0.0415(14) 0.0138(13) 0.0012(12) -0.0027(12) C43 0.0465(15) 0.0536(16) 0.0551(16) 0.0055(13) -0.0036(12) 0.0062(12) C44' 0.0300(19) 0.089(3) 0.078(3) 0.001(3) 0.0072(18) 0.009(2) C44 0.072(8) 0.113(13) 0.063(8) 0.030(9) 0.015(6) 0.020(8) C45' 0.043(2) 0.066(3) 0.096(4) 0.024(2) 0.006(2) -0.0059(18) C45 0.049(6) 0.075(9) 0.086(9) -0.004(7) 0.001(6) 0.017(6) C46' 0.051(2) 0.086(4) 0.074(3) 0.022(3) -0.0116(19) 0.012(2) C46 0.125(11) 0.067(8) 0.088(10) 0.027(7) 0.019(8) 0.026(8) C47 0.0509(15) 0.0621(16) 0.0484(15) 0.0108(13) 0.0069(12) -0.0046(13) C48 0.081(2) 0.117(3) 0.078(2) -0.044(2) 0.0211(18) -0.021(2) C49 0.109(2) 0.0596(18) 0.072(2) 0.0150(15) 0.0270(18) 0.0170(17) C50 0.081(2) 0.080(2) 0.0544(17) 0.0179(15) 0.0213(15) 0.0069(16) _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 O1 C17 1.357(2) . ? O1 H1 0.98(3) . ? N1 C1 1.366(3) . ? N1 C4 1.369(3) . ? N1 C5 1.423(3) . ? N2 C11 1.281(3) . ? N2 C8 1.415(3) . ? C1 C2 1.359(3) . ? C1 H1A 0.9500 . ? C2 C3 1.405(3) . ? C2 H2A 0.9500 . ? C3 C4 1.359(3) . ? C3 H3A 0.9500 . ? C4 H4A 0.9500 . ? C5 C10 1.386(3) . ? C5 C6 1.388(3) . ? C6 C7 1.380(3) . ? C6 H6A 0.9500 . ? C7 C8 1.386(3) . ? C7 H7A 0.9500 . ? C8 C9 1.384(3) . ? C9 C10 1.378(3) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C11 C12 1.446(3) . ? C11 H11A 0.9500 . ? C12 C17 1.402(3) . ? C12 C13 1.403(3) . ? C13 C14 1.373(3) . ? C13 H13A 0.9500 . ? C14 C15 1.405(3) . ? C14 C22 1.533(3) . ? C15 C16 1.391(3) . ? C15 H15A 0.9500 . ? C16 C17 1.404(3) . ? C16 C18 1.529(3) . ? C18 C20 1.531(3) . ? C18 C21 1.536(3) . ? C18 C19 1.538(3) . ? C19 H19C 0.9800 . ? C19 H19B 0.9800 . ? C19 H19A 0.9800 . ? C20 H20C 0.9800 . ? C20 H20B 0.9800 . ? C20 H20A 0.9800 . ? C21 H21C 0.9800 . ? C21 H21B 0.9800 . ? C21 H21A 0.9800 . ? C22 C25 1.526(4) . ? C22 C23 1.527(4) . ? C22 C24 1.530(4) . ? C23 H23C 0.9800 . ? C23 H23B 0.9800 . ? C23 H23A 0.9800 . ? C24 H24C 0.9800 . ? C24 H24B 0.9800 . ? C24 H24A 0.9800 . ? C25 H25C 0.9800 . ? C25 H25B 0.9800 . ? C25 H25A 0.9800 . ? O2 C38 1.341(3) . ? O2 H2 1.02(4) . ? O2' C42 1.080(13) . ? O2' H2' 0.8400 . ? N3 C29 1.368(3) . ? N3 C26 1.374(3) . ? N3 C30 1.418(3) . ? N4 C36 1.282(4) . ? N4 C33 1.427(3) . ? N4' C36' 1.25(4) . ? N4' C33 1.63(2) . ? C26 C27 1.354(3) . ? C26 H26A 0.9500 . ? C27 C28 1.407(3) . ? C27 H27A 0.9500 . ? C28 C29 1.358(3) . ? C28 H28A 0.9500 . ? C29 H29A 0.9500 . ? C30 C35 1.383(3) . ? C30 C31 1.390(3) . ? C31 C32 1.372(3) . ? C31 H31A 0.9500 . ? C32 C33 1.374(3) . ? C32 H32A 0.9500 . ? C33 C34 1.398(3) . ? C34 C35 1.388(3) . ? C34 H34A 0.9500 . ? C35 H35A 0.9500 . ? C36 C37 1.468(4) . ? C36 H36A 0.9500 . ? C36' C37 1.56(3) . ? C36' H2 1.36(4) . ? C36' H36B 0.9500 . ? C37 C42 1.386(3) . ? C37 C38 1.402(3) . ? C38 C39 1.416(3) . ? C38 H38A 0.9500 . ? C39 C40 1.391(3) . ? C39 C47 1.534(3) . ? C40 C41 1.408(3) . ? C40 H40A 0.9500 . ? C41 C42 1.377(3) . ? C41 C43 1.530(3) . ? C42 H42A 0.9500 . ? C43 C44 1.396(11) . ? C43 C45 1.509(10) . ? C43 C46' 1.516(4) . ? C43 C44' 1.554(4) . ? C43 C45' 1.568(4) . ? C43 C46 1.602(11) . ? C44' H44F 0.9800 . ? C44' H44E 0.9800 . ? C44' H44D 0.9800 . ? C44 H44C 0.9800 . ? C44 H44B 0.9800 . ? C44 H44A 0.9800 . ? C45' H45F 0.9800 . ? C45' H45E 0.9800 . ? C45' H45D 0.9800 . ? C45 H45C 0.9800 . ? C45 H45B 0.9800 . ? C45 H45A 0.9800 . ? C46' H46F 0.9800 . ? C46' H46E 0.9800 . ? C46' H46D 0.9800 . ? C46 H46C 0.9800 . ? C46 H46B 0.9800 . ? C46 H46A 0.9800 . ? C47 C48 1.513(3) . ? C47 C50 1.535(3) . ? C47 C49 1.535(4) . ? C48 H48C 0.9800 . ? C48 H48B 0.9800 . ? C48 H48A 0.9800 . ? C49 H49C 0.9800 . ? C49 H49B 0.9800 . ? C49 H49A 0.9800 . ? C50 H50C 0.9800 . ? C50 H50B 0.9800 . ? C50 H50A 0.9800 . ? 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 C17 O1 H1 104.1(16) . . ? C1 N1 C4 108.33(18) . . ? C1 N1 C5 126.12(18) . . ? C4 N1 C5 125.55(19) . . ? C11 N2 C8 121.0(2) . . ? C2 C1 N1 108.2(2) . . ? C2 C1 H1A 125.9 . . ? N1 C1 H1A 125.9 . . ? C1 C2 C3 107.9(2) . . ? C1 C2 H2A 126.1 . . ? C3 C2 H2A 126.1 . . ? C4 C3 C2 107.0(2) . . ? C4 C3 H3A 126.5 . . ? C2 C3 H3A 126.5 . . ? C3 C4 N1 108.7(2) . . ? C3 C4 H4A 125.7 . . ? N1 C4 H4A 125.7 . . ? C10 C5 C6 119.4(2) . . ? C10 C5 N1 120.13(19) . . ? C6 C5 N1 120.5(2) . . ? C7 C6 C5 120.2(2) . . ? C7 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? C6 C7 C8 120.7(2) . . ? C6 C7 H7A 119.6 . . ? C8 C7 H7A 119.6 . . ? C9 C8 C7 118.5(2) . . ? C9 C8 N2 117.4(2) . . ? C7 C8 N2 124.1(2) . . ? C10 C9 C8 121.3(2) . . ? C10 C9 H9A 119.3 . . ? C8 C9 H9A 119.3 . . ? C9 C10 C5 119.8(2) . . ? C9 C10 H10A 120.1 . . ? C5 C10 H10A 120.1 . . ? N2 C11 C12 123.0(2) . . ? N2 C11 H11A 118.5 . . ? C12 C11 H11A 118.5 . . ? C17 C12 C13 119.6(2) . . ? C17 C12 C11 122.0(2) . . ? C13 C12 C11 118.4(2) . . ? C14 C13 C12 121.5(2) . . ? C14 C13 H13A 119.2 . . ? C12 C13 H13A 119.2 . . ? C13 C14 C15 117.1(2) . . ? C13 C14 C22 122.7(2) . . ? C15 C14 C22 120.2(2) . . ? C16 C15 C14 124.2(2) . . ? C16 C15 H15A 117.9 . . ? C14 C15 H15A 117.9 . . ? C15 C16 C17 116.7(2) . . ? C15 C16 C18 121.98(19) . . ? C17 C16 C18 121.3(2) . . ? O1 C17 C12 119.40(19) . . ? O1 C17 C16 119.8(2) . . ? C12 C17 C16 120.8(2) . . ? C16 C18 C20 112.08(19) . . ? C16 C18 C21 109.07(19) . . ? C20 C18 C21 107.8(2) . . ? C16 C18 C19 110.1(2) . . ? C20 C18 C19 107.1(2) . . ? C21 C18 C19 110.6(2) . . ? C18 C19 H19C 109.5 . . ? C18 C19 H19B 109.5 . . ? H19C C19 H19B 109.5 . . ? C18 C19 H19A 109.5 . . ? H19C C19 H19A 109.5 . . ? H19B C19 H19A 109.5 . . ? C18 C20 H20C 109.5 . . ? C18 C20 H20B 109.5 . . ? H20C C20 H20B 109.5 . . ? C18 C20 H20A 109.5 . . ? H20C C20 H20A 109.5 . . ? H20B C20 H20A 109.5 . . ? C18 C21 H21C 109.5 . . ? C18 C21 H21B 109.5 . . ? H21C C21 H21B 109.5 . . ? C18 C21 H21A 109.5 . . ? H21C C21 H21A 109.5 . . ? H21B C21 H21A 109.5 . . ? C25 C22 C23 110.3(3) . . ? C25 C22 C24 108.8(2) . . ? C23 C22 C24 106.8(2) . . ? C25 C22 C14 109.1(2) . . ? C23 C22 C14 111.2(2) . . ? C24 C22 C14 110.6(2) . . ? C22 C23 H23C 109.5 . . ? C22 C23 H23B 109.5 . . ? H23C C23 H23B 109.5 . . ? C22 C23 H23A 109.5 . . ? H23C C23 H23A 109.5 . . ? H23B C23 H23A 109.5 . . ? C22 C24 H24C 109.5 . . ? C22 C24 H24B 109.5 . . ? H24C C24 H24B 109.5 . . ? C22 C24 H24A 109.5 . . ? H24C C24 H24A 109.5 . . ? H24B C24 H24A 109.5 . . ? C22 C25 H25C 109.5 . . ? C22 C25 H25B 109.5 . . ? H25C C25 H25B 109.5 . . ? C22 C25 H25A 109.5 . . ? H25C C25 H25A 109.5 . . ? H25B C25 H25A 109.5 . . ? C38 O2 H2 103.5(18) . . ? C42 O2' H2' 109.5 . . ? C29 N3 C26 107.54(19) . . ? C29 N3 C30 126.0(2) . . ? C26 N3 C30 126.45(19) . . ? C36 N4 C33 118.4(3) . . ? C36' N4' C33 106(2) . . ? C27 C26 N3 109.1(2) . . ? C27 C26 H26A 125.5 . . ? N3 C26 H26A 125.5 . . ? C26 C27 C28 107.1(2) . . ? C26 C27 H27A 126.5 . . ? C28 C27 H27A 126.5 . . ? C29 C28 C27 107.5(2) . . ? C29 C28 H28A 126.3 . . ? C27 C28 H28A 126.3 . . ? C28 C29 N3 108.8(2) . . ? C28 C29 H29A 125.6 . . ? N3 C29 H29A 125.6 . . ? C35 C30 C31 119.0(2) . . ? C35 C30 N3 120.8(2) . . ? C31 C30 N3 120.1(2) . . ? C32 C31 C30 120.8(2) . . ? C32 C31 H31A 119.6 . . ? C30 C31 H31A 119.6 . . ? C31 C32 C33 121.1(2) . . ? C31 C32 H32A 119.4 . . ? C33 C32 H32A 119.4 . . ? C32 C33 C34 118.3(2) . . ? C32 C33 N4 116.8(2) . . ? C34 C33 N4 124.8(2) . . ? C32 C33 N4' 150.5(9) . . ? C34 C33 N4' 88.6(9) . . ? N4 C33 N4' 39.4(9) . . ? C35 C34 C33 120.9(2) . . ? C35 C34 H34A 119.5 . . ? C33 C34 H34A 119.5 . . ? C30 C35 C34 119.8(2) . . ? C30 C35 H35A 120.1 . . ? C34 C35 H35A 120.1 . . ? N4 C36 C37 121.1(3) . . ? N4 C36 H36A 119.4 . . ? C37 C36 H36A 119.4 . . ? N4' C36' C37 107(3) . . ? N4' C36' H2 144(3) . . ? C37 C36' H2 103(2) . . ? N4' C36' H36B 126.5 . . ? C37 C36' H36B 126.5 . . ? H2 C36' H36B 30.7 . . ? C42 C37 C38 120.0(2) . . ? C42 C37 C36 117.0(2) . . ? C38 C37 C36 122.9(2) . . ? C42 C37 C36' 150.2(10) . . ? C38 C37 C36' 89.2(10) . . ? C36 C37 C36' 34.9(9) . . ? O2 C38 C37 119.3(2) . . ? O2 C38 C39 120.0(2) . . ? C37 C38 C39 120.7(2) . . ? O2 C38 H38A 2.0 . . ? C37 C38 H38A 119.6 . . ? C39 C38 H38A 119.6 . . ? C40 C39 C38 116.2(2) . . ? C40 C39 C47 121.7(2) . . ? C38 C39 C47 122.1(2) . . ? C39 C40 C41 124.3(2) . . ? C39 C40 H40A 117.8 . . ? C41 C40 H40A 117.8 . . ? C42 C41 C40 117.1(2) . . ? C42 C41 C43 122.0(2) . . ? C40 C41 C43 120.9(2) . . ? O2' C42 C41 146.3(8) . . ? O2' C42 C37 92.0(8) . . ? C41 C42 C37 121.7(3) . . ? O2' C42 H42A 27.2 . . ? C41 C42 H42A 119.2 . . ? C37 C42 H42A 119.2 . . ? C44 C43 C45 118.3(8) . . ? C44 C43 C46' 139.0(6) . . ? C45 C43 C46' 55.4(5) . . ? C44 C43 C41 108.4(5) . . ? C45 C43 C41 109.5(4) . . ? C46' C43 C41 111.4(2) . . ? C44 C43 C44' 44.2(6) . . ? C45 C43 C44' 137.1(4) . . ? C46' C43 C44' 108.7(3) . . ? C41 C43 C44' 113.3(2) . . ? C44 C43 C45' 65.7(6) . . ? C45 C43 C45' 56.3(5) . . ? C46' C43 C45' 107.8(3) . . ? C41 C43 C45' 110.2(2) . . ? C44' C43 C45' 105.1(3) . . ? C44 C43 C46 114.0(8) . . ? C45 C43 C46 105.7(7) . . ? C46' C43 C46 50.4(5) . . ? C41 C43 C46 99.2(5) . . ? C44' C43 C46 69.9(5) . . ? C45' C43 C46 149.2(6) . . ? C43 C44' H44F 109.5 . . ? C43 C44' H44E 109.5 . . ? C43 C44' H44D 109.5 . . ? C43 C44 H44C 109.5 . . ? C43 C44 H44B 109.5 . . ? H44C C44 H44B 109.5 . . ? C43 C44 H44A 109.5 . . ? H44C C44 H44A 109.5 . . ? H44B C44 H44A 109.5 . . ? C43 C45' H45F 109.5 . . ? C43 C45' H45E 109.5 . . ? C43 C45' H45D 109.5 . . ? C43 C45 H45C 109.5 . . ? C43 C45 H45B 109.5 . . ? H45C C45 H45B 109.5 . . ? C43 C45 H45A 109.5 . . ? H45C C45 H45A 109.5 . . ? H45B C45 H45A 109.5 . . ? C43 C46' H46F 109.5 . . ? C43 C46' H46E 109.5 . . ? C43 C46' H46D 109.5 . . ? C43 C46 H46C 109.5 . . ? C43 C46 H46B 109.5 . . ? H46C C46 H46B 109.5 . . ? C43 C46 H46A 109.5 . . ? H46C C46 H46A 109.5 . . ? H46B C46 H46A 109.5 . . ? C48 C47 C39 112.4(2) . . ? C48 C47 C50 107.9(2) . . ? C39 C47 C50 109.5(2) . . ? C48 C47 C49 107.9(2) . . ? C39 C47 C49 110.0(2) . . ? C50 C47 C49 109.1(2) . . ? C47 C48 H48C 109.5 . . ? C47 C48 H48B 109.5 . . ? H48C C48 H48B 109.5 . . ? C47 C48 H48A 109.5 . . ? H48C C48 H48A 109.5 . . ? H48B C48 H48A 109.5 . . ? C47 C49 H49C 109.5 . . ? C47 C49 H49B 109.5 . . ? H49C C49 H49B 109.5 . . ? C47 C49 H49A 109.5 . . ? H49C C49 H49A 109.5 . . ? H49B C49 H49A 109.5 . . ? C47 C50 H50C 109.5 . . ? C47 C50 H50B 109.5 . . ? H50C C50 H50B 109.5 . . ? C47 C50 H50A 109.5 . . ? H50C C50 H50A 109.5 . . ? H50B C50 H50A 109.5 . . ? 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 O2 H2 N4 1.02(4) 1.63(4) 2.596(3) 156(3) . O1 H1 N2 0.98(3) 1.67(3) 2.591(2) 155(2) . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.261 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.034