# 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 "Donal O'Shea" _publ_contact_author_address ; Chemistry University College Dublin Belfield Dublin 4 4 REPUBLIC OF IRELAND ; _publ_contact_author_email DONAL.F.OSHEA@UCD.IE _publ_section_title ; A Study of the Effects of Subunit Pre-orientation for Diarylpyrrole esters; Design of New Aryl-Heteroaryl Fluorescent Sensors ; loop_ _publ_author_name D.O'Shea 'J.F. Gallagher' 'John Killoran' 'Paul V. Murphy' #================================================================== data_(I) _database_code_depnum_ccdc_archive 'CCDC 233393' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-Diphenyl-1H-pyrrole-2-carboxylic acid ethyl ester ; _chemical_name_common '3,5-Diphenyl-1H-pyrrole-2-carboxylic acid ethyl ester' _chemical_melting_point 412 _chemical_formula_moiety 'C19 H17 N O2' _chemical_formula_sum 'C19 H17 N O2' _chemical_formula_weight 291.34 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 'P 21/c' _symmetry_space_group_name_Hall '-p 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5232(12) _cell_length_b 7.5048(4) _cell_length_c 20.2461(15) _cell_angle_alpha 90 _cell_angle_beta 102.020(7) _cell_angle_gamma 90 _cell_volume 1563.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 85 _cell_measurement_theta_min 6.94 _cell_measurement_theta_max 18.88 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'Siemens P4' _diffrn_measurement_method /w _diffrn_standards_number 4 _diffrn_standards_interval_count 296 _diffrn_standards_decay_% 1 _diffrn_reflns_number 4173 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_sigmaI/netI 0.037 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.0 _diffrn_reflns_theta_max 26.0 _diffrn_measured_fraction_theta_max 1.00 _diffrn_reflns_theta_full 26.0 _diffrn_measured_fraction_theta_full 1.00 _reflns_number_total 3081 _reflns_number_gt 2189 _reflns_threshold_expression >2\s(I) _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_cell_refinement 'XSCANS (Siemens, 1996)' _computing_data_reduction 'XSCANS (Siemens, 1996)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002), ORTEX (McArdle, 1995)' _computing_publication_material 'PLATON (Spek, 2002), PREP8 (Ferguson, 1998)' _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^)+(0.0466P)^2^+0.3335P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3081 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.1018 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.21 _refine_diff_density_min -0.19 _refine_diff_density_rms 0.05 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 0.06896(13) 0.10083(17) 0.06866(6) 0.0645(4) Uani 1 1 d . . . O2 O 0.22181(12) 0.30052(17) 0.11184(6) 0.0592(3) Uani 1 1 d . . . N1 N 0.03471(14) 0.26533(19) -0.05616(7) 0.0460(3) Uani 1 1 d . . . H1 H -0.0087(17) 0.170(3) -0.0566(9) 0.055(5) Uiso 1 1 d . . . C1 C 0.03206(15) 0.3739(2) -0.11010(8) 0.0464(4) Uani 1 1 d . . . C2 C 0.12451(16) 0.5039(2) -0.08972(8) 0.0516(4) Uani 1 1 d . . . H2 H 0.1436 0.5964 -0.1166 0.062 Uiso 1 1 calc R . . C3 C 0.18519(15) 0.4746(2) -0.02211(8) 0.0473(4) Uani 1 1 d . . . C4 C 0.12686(15) 0.3228(2) -0.00201(8) 0.0447(4) Uani 1 1 d . . . C5 C 0.13518(16) 0.2296(2) 0.06169(8) 0.0467(4) Uani 1 1 d . . . C6 C 0.2377(2) 0.2209(3) 0.17788(9) 0.0701(6) Uani 1 1 d . . . H6A H 0.2169 0.0949 0.1737 0.084 Uiso 1 1 calc R . . H6B H 0.1796 0.2771 0.2030 0.084 Uiso 1 1 calc R . . C7 C 0.3722(2) 0.2452(4) 0.21307(13) 0.1100(10) Uani 1 1 d . . . H7A H 0.4283 0.1773 0.1908 0.165 Uiso 1 1 calc R . . H7B H 0.3822 0.2053 0.2589 0.165 Uiso 1 1 calc R . . H7C H 0.3947 0.3691 0.2126 0.165 Uiso 1 1 calc R . . C11 C -0.05949(16) 0.3533(2) -0.17497(8) 0.0465(4) Uani 1 1 d . . . C12 C -0.17885(17) 0.2704(2) -0.17955(9) 0.0556(4) Uani 1 1 d . . . H12 H -0.2006 0.2218 -0.1411 0.067 Uiso 1 1 calc R . . C13 C -0.26566(18) 0.2598(3) -0.24088(10) 0.0662(5) Uani 1 1 d . . . H13 H -0.3448 0.2021 -0.2435 0.079 Uiso 1 1 calc R . . C14 C -0.2365(2) 0.3334(3) -0.29799(9) 0.0670(5) Uani 1 1 d . . . H14 H -0.2960 0.3274 -0.3389 0.080 Uiso 1 1 calc R . . C15 C -0.1182(2) 0.4164(3) -0.29420(9) 0.0668(5) Uani 1 1 d . . . H15 H -0.0976 0.4659 -0.3328 0.080 Uiso 1 1 calc R . . C16 C -0.03039(19) 0.4262(3) -0.23333(8) 0.0589(5) Uani 1 1 d . . . H16 H 0.0492 0.4822 -0.2312 0.071 Uiso 1 1 calc R . . C31 C 0.28900(17) 0.5912(2) 0.01582(8) 0.0526(4) Uani 1 1 d . . . C32 C 0.2766(2) 0.7752(3) 0.00753(10) 0.0655(5) Uani 1 1 d . . . H32 H 0.2022 0.8225 -0.0198 0.079 Uiso 1 1 calc R . . C33 C 0.3741(2) 0.8879(3) 0.03953(12) 0.0850(7) Uani 1 1 d . . . H33 H 0.3647 1.0105 0.0337 0.102 Uiso 1 1 calc R . . C34 C 0.4841(3) 0.8203(4) 0.07978(13) 0.0953(9) Uani 1 1 d . . . H34 H 0.5490 0.8969 0.1015 0.114 Uiso 1 1 calc R . . C35 C 0.4988(2) 0.6384(4) 0.08820(11) 0.0829(7) Uani 1 1 d . . . H35 H 0.5738 0.5924 0.1154 0.100 Uiso 1 1 calc R . . C36 C 0.40181(17) 0.5245(3) 0.05618(9) 0.0646(5) Uani 1 1 d . . . H36 H 0.4124 0.4020 0.0618 0.078 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 0.0818(9) 0.0527(7) 0.0541(7) 0.0055(6) 0.0032(6) -0.0226(7) O2 0.0641(7) 0.0628(8) 0.0449(6) 0.0038(6) -0.0020(6) -0.0170(6) N1 0.0518(8) 0.0408(8) 0.0441(7) 0.0005(6) 0.0069(6) -0.0086(7) C1 0.0530(9) 0.0427(9) 0.0444(8) -0.0012(7) 0.0117(7) -0.0017(8) C2 0.0611(10) 0.0464(9) 0.0489(9) 0.0025(8) 0.0149(8) -0.0098(8) C3 0.0492(9) 0.0471(9) 0.0463(8) -0.0038(7) 0.0114(7) -0.0069(8) C4 0.0466(9) 0.0437(9) 0.0420(8) -0.0026(7) 0.0055(7) -0.0053(7) C5 0.0487(9) 0.0425(9) 0.0468(9) -0.0010(7) 0.0052(7) -0.0029(8) C6 0.0817(14) 0.0757(13) 0.0469(10) 0.0084(10) -0.0006(9) -0.0030(11) C7 0.0910(18) 0.138(3) 0.0817(16) 0.0226(16) -0.0256(14) -0.0093(17) C11 0.0548(10) 0.0412(9) 0.0433(8) -0.0021(7) 0.0095(7) 0.0030(8) C12 0.0547(10) 0.0606(11) 0.0501(10) 0.0044(8) 0.0075(8) -0.0005(9) C13 0.0548(11) 0.0732(13) 0.0643(12) -0.0019(10) -0.0017(9) 0.0003(10) C14 0.0760(13) 0.0684(12) 0.0481(10) -0.0043(9) -0.0065(9) 0.0174(11) C15 0.0927(15) 0.0637(12) 0.0429(9) 0.0016(9) 0.0114(10) 0.0064(11) C16 0.0717(12) 0.0578(11) 0.0483(10) -0.0026(8) 0.0147(9) -0.0059(9) C31 0.0553(10) 0.0586(11) 0.0472(9) -0.0079(8) 0.0182(8) -0.0177(9) C32 0.0746(13) 0.0596(12) 0.0672(12) -0.0079(10) 0.0259(10) -0.0215(10) C33 0.1004(18) 0.0711(14) 0.0906(16) -0.0224(13) 0.0364(14) -0.0402(14) C34 0.0896(18) 0.113(2) 0.0871(17) -0.0374(16) 0.0274(14) -0.0591(17) C35 0.0625(13) 0.117(2) 0.0680(13) -0.0199(13) 0.0112(10) -0.0290(14) C36 0.0568(11) 0.0789(13) 0.0583(10) -0.0092(10) 0.0124(9) -0.0174(10) _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 C5 1.2166(19) . ? O2 C5 1.3267(19) . ? O2 C6 1.442(2) . ? N1 C1 1.358(2) . ? N1 C4 1.373(2) . ? C1 C2 1.379(2) . ? C1 C11 1.466(2) . ? C2 C3 1.402(2) . ? C3 C4 1.394(2) . ? C3 C31 1.483(2) . ? C4 C5 1.454(2) . ? C6 C7 1.458(3) . ? C11 C12 1.387(2) . ? C11 C16 1.393(2) . ? C12 C13 1.382(2) . ? C13 C14 1.373(3) . ? C14 C15 1.380(3) . ? C15 C16 1.380(3) . ? C31 C32 1.394(3) . ? C31 C36 1.387(3) . ? C32 C33 1.382(3) . ? C33 C34 1.367(4) . ? C34 C35 1.380(4) . ? C35 C36 1.384(3) . ? N1 H1 0.848(19) . ? C2 H2 0.9300 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? 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 C5 O2 C6 118.13(14) . . ? C1 N1 C4 110.27(14) . . ? N1 C1 C2 106.77(14) . . ? N1 C1 C11 123.81(14) . . ? C2 C1 C11 129.34(15) . . ? C1 C2 C3 109.32(14) . . ? C4 C3 C2 105.93(14) . . ? C4 C3 C31 130.73(15) . . ? C2 C3 C31 123.33(15) . . ? N1 C4 C3 107.70(14) . . ? N1 C4 C5 117.34(14) . . ? C3 C4 C5 134.69(15) . . ? O1 C5 O2 123.29(15) . . ? O1 C5 C4 123.71(15) . . ? O2 C5 C4 113.00(14) . . ? O2 C6 C7 108.31(18) . . ? C12 C11 C16 118.39(15) . . ? C12 C11 C1 121.60(15) . . ? C16 C11 C1 119.92(15) . . ? C13 C12 C11 120.39(17) . . ? C14 C13 C12 120.76(19) . . ? C13 C14 C15 119.50(18) . . ? C16 C15 C14 120.14(18) . . ? C15 C16 C11 120.81(18) . . ? C36 C31 C32 118.37(18) . . ? C36 C31 C3 122.69(17) . . ? C32 C31 C3 118.82(17) . . ? C33 C32 C31 120.6(2) . . ? C34 C33 C32 120.4(2) . . ? C33 C34 C35 120.0(2) . . ? C34 C35 C36 120.0(2) . . ? C35 C36 C31 120.7(2) . . ? C1 N1 H1 125.2(12) . . ? C4 N1 H1 124.3(12) . . ? C1 C2 H2 125.3 . . ? C3 C2 H2 125.3 . . ? O2 C6 H6A 110.0 . . ? C7 C6 H6A 110.0 . . ? O2 C6 H6B 110.0 . . ? C7 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C35 C36 H36 119.7 . . ? C31 C36 H36 119.7 . . ? 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 C4 N1 C1 C2 -0.16(18) . . . . ? C4 N1 C1 C11 -177.33(14) . . . . ? N1 C1 C2 C3 0.08(19) . . . . ? C11 C1 C2 C3 177.04(16) . . . . ? C1 C2 C3 C4 0.02(19) . . . . ? C1 C2 C3 C31 -179.51(15) . . . . ? C1 N1 C4 C3 0.18(18) . . . . ? C1 N1 C4 C5 175.15(14) . . . . ? C2 C3 C4 N1 -0.12(18) . . . . ? C31 C3 C4 N1 179.37(17) . . . . ? C2 C3 C4 C5 -173.83(18) . . . . ? C31 C3 C4 C5 5.7(3) . . . . ? C6 O2 C5 O1 -0.2(3) . . . . ? C6 O2 C5 C4 179.20(15) . . . . ? N1 C4 C5 O1 2.9(3) . . . . ? C3 C4 C5 O1 176.13(18) . . . . ? N1 C4 C5 O2 -176.48(14) . . . . ? C3 C4 C5 O2 -3.2(3) . . . . ? C5 O2 C6 C7 149.2(2) . . . . ? N1 C1 C11 C12 25.2(2) . . . . ? C2 C1 C11 C12 -151.26(18) . . . . ? N1 C1 C11 C16 -158.27(16) . . . . ? C2 C1 C11 C16 25.2(3) . . . . ? C16 C11 C12 C13 0.6(3) . . . . ? C1 C11 C12 C13 177.12(17) . . . . ? C11 C12 C13 C14 -1.1(3) . . . . ? C12 C13 C14 C15 1.0(3) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? C14 C15 C16 C11 -0.1(3) . . . . ? C12 C11 C16 C15 0.0(3) . . . . ? C1 C11 C16 C15 -176.56(16) . . . . ? C4 C3 C31 C36 45.8(3) . . . . ? C2 C3 C31 C36 -134.75(18) . . . . ? C4 C3 C31 C32 -138.10(19) . . . . ? C2 C3 C31 C32 41.3(2) . . . . ? C36 C31 C32 C33 -0.8(3) . . . . ? C3 C31 C32 C33 -176.98(16) . . . . ? C31 C32 C33 C34 0.0(3) . . . . ? C32 C33 C34 C35 0.5(4) . . . . ? C33 C34 C35 C36 -0.3(4) . . . . ? C34 C35 C36 C31 -0.4(3) . . . . ? C32 C31 C36 C35 1.0(3) . . . . ? C3 C31 C36 C35 177.02(16) . . . . ? 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 N1 H1 O1 0.848(19) 2.128(19) 2.9480(18) 162.6(16) 3 #============================================================ data_(II) _database_code_depnum_ccdc_archive 'CCDC 233394' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-(4-Dimethylamino-phenyl)-5-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester ; _chemical_name_common ;3-(4-Dimethylamino-phenyl)-5-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester ; _chemical_melting_point 439 _chemical_formula_moiety 'C21 H22 N2 O2' _chemical_formula_sum 'C21 H22 N2 O2' _chemical_formula_weight 334.41 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' _symmetry_space_group_name_Hall '-p 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8173(11) _cell_length_b 13.3363(11) _cell_length_c 15.9016(10) _cell_angle_alpha 67.237(5) _cell_angle_beta 80.480(8) _cell_angle_gamma 72.421(8) _cell_volume 1827.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 72 _cell_measurement_theta_min 5.6 _cell_measurement_theta_max 35.63 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.971 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'Siemens P4' _diffrn_measurement_method /w _diffrn_standards_number 4 _diffrn_standards_interval_count 296 _diffrn_standards_decay_% 1 _diffrn_reflns_number 8324 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_av_sigmaI/netI 0.031 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.2 _diffrn_reflns_theta_max 26.0 _diffrn_measured_fraction_theta_max 1.00 _diffrn_reflns_theta_full 26.0 _diffrn_measured_fraction_theta_full 1.00 _reflns_number_total 7032 _reflns_number_gt 4257 _reflns_threshold_expression >2\s(I) _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_cell_refinement 'XSCANS (Siemens, 1996)' _computing_data_reduction 'XSCANS (Siemens, 1996)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002), ORTEX (McArdle, 1995)' _computing_publication_material 'PLATON (Spek, 2002), PREP8 (Ferguson, 1998)' _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^)+(0.0651P)^2^+0.2011P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7032 _refine_ls_number_parameters 468 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0997 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1408 _refine_ls_wR_factor_gt 0.1187 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.34 _refine_diff_density_min -0.32 _refine_diff_density_rms 0.15 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 O1A O 0.17632(18) 0.56100(12) 0.99586(10) 0.0742(5) Uani 1 1 d . . . O2A O 0.14885(16) 0.74579(12) 0.92194(9) 0.0656(4) Uani 1 1 d . . . N1A N 0.42332(19) 0.51566(15) 0.88989(12) 0.0580(5) Uani 1 1 d . . . H1A H 0.406(2) 0.4544(19) 0.9389(16) 0.073(7) Uiso 1 1 d . . . C1A C 0.5359(2) 0.51506(18) 0.82725(13) 0.0551(5) Uani 1 1 d . . . C2A C 0.5185(2) 0.62454(18) 0.76715(14) 0.0584(5) Uani 1 1 d . . . H2A H 0.5804 0.6489 0.7172 0.070 Uiso 1 1 calc R . . C3A C 0.3928(2) 0.69399(17) 0.79269(13) 0.0537(5) Uani 1 1 d . . . C4A C 0.3356(2) 0.62307(17) 0.87120(14) 0.0545(5) Uani 1 1 d . . . C5A C 0.2143(2) 0.63816(18) 0.93516(14) 0.0556(5) Uani 1 1 d . . . C6A C 0.0200(3) 0.76711(19) 0.97834(15) 0.0691(6) Uani 1 1 d . . . H6A1 H 0.0404 0.7323 1.0425 0.083 Uiso 1 1 calc R . . H6A2 H -0.0514 0.7369 0.9680 0.083 Uiso 1 1 calc R . . C7A C -0.0324(3) 0.8917(2) 0.9515(2) 0.1055(10) Uani 1 1 d . . . H7A1 H 0.0387 0.9202 0.9630 0.158 Uiso 1 1 calc R . . H7A2 H -0.1193 0.9103 0.9866 0.158 Uiso 1 1 calc R . . H7A3 H -0.0504 0.9250 0.8877 0.158 Uiso 1 1 calc R . . C11A C 0.6460(2) 0.41347(18) 0.82574(14) 0.0549(5) Uani 1 1 d . . . C12A C 0.6283(3) 0.30610(19) 0.87379(16) 0.0716(7) Uani 1 1 d . . . H12A H 0.5444 0.2976 0.9095 0.086 Uiso 1 1 calc R . . C13A C 0.7328(3) 0.2117(2) 0.86962(17) 0.0759(7) Uani 1 1 d . . . H13A H 0.7187 0.1404 0.9024 0.091 Uiso 1 1 calc R . . C14A C 0.8571(3) 0.2223(2) 0.81750(16) 0.0691(6) Uani 1 1 d . . . H14A H 0.9274 0.1587 0.8146 0.083 Uiso 1 1 calc R . . C15A C 0.8767(3) 0.3275(2) 0.76972(17) 0.0717(6) Uani 1 1 d . . . H15A H 0.9610 0.3354 0.7344 0.086 Uiso 1 1 calc R . . C16A C 0.7724(2) 0.4217(2) 0.77355(15) 0.0648(6) Uani 1 1 d . . . H16A H 0.7872 0.4925 0.7403 0.078 Uiso 1 1 calc R . . C31A C 0.3393(2) 0.81576(17) 0.73845(13) 0.0524(5) Uani 1 1 d . . . C32A C 0.4368(2) 0.87825(18) 0.69002(14) 0.0591(5) Uani 1 1 d . . . H32A H 0.5342 0.8429 0.6944 0.071 Uiso 1 1 calc R . . C33A C 0.3944(2) 0.99033(18) 0.63606(15) 0.0622(6) Uani 1 1 d . . . H33A H 0.4632 1.0288 0.6052 0.075 Uiso 1 1 calc R . . C34A C 0.2496(2) 1.04726(18) 0.62685(14) 0.0568(5) Uani 1 1 d . . . C35A C 0.1511(2) 0.98493(18) 0.67348(14) 0.0578(5) Uani 1 1 d . . . H35A H 0.0537 1.0198 0.6683 0.069 Uiso 1 1 calc R . . C36A C 0.1955(2) 0.87227(18) 0.72728(13) 0.0561(5) Uani 1 1 d . . . H36A H 0.1270 0.8331 0.7569 0.067 Uiso 1 1 calc R . . N34A N 0.2057(2) 1.16052(16) 0.57282(14) 0.0760(6) Uani 1 1 d . . . C37A C 0.3094(3) 1.2200(2) 0.51975(19) 0.0899(8) Uani 1 1 d . . . H37A H 0.3692 1.2238 0.5599 0.135 Uiso 1 1 calc R . . H37B H 0.2610 1.2949 0.4827 0.135 Uiso 1 1 calc R . . H37C H 0.3673 1.1811 0.4812 0.135 Uiso 1 1 calc R . . C38A C 0.0589(3) 1.2209(2) 0.57081(18) 0.0885(8) Uani 1 1 d . . . H38A H 0.0088 1.1966 0.5384 0.133 Uiso 0.81(3) 1 calc PR . . H38B H 0.0507 1.3001 0.5405 0.133 Uiso 0.81(3) 1 calc PR . . H38C H 0.0181 1.2067 0.6321 0.133 Uiso 0.81(3) 1 calc PR . . H38D H 0.0429 1.2723 0.6023 0.133 Uiso 0.19(3) 1 calc PR . . H38E H 0.0010 1.1689 0.6002 0.133 Uiso 0.19(3) 1 calc PR . . H38F H 0.0336 1.2622 0.5086 0.133 Uiso 0.19(3) 1 calc PR . . O1B O 0.35788(19) 0.30627(13) 1.04218(10) 0.0804(5) Uani 1 1 d . . . O2B O 0.41612(16) 0.13001(12) 1.14159(10) 0.0702(4) Uani 1 1 d . . . N1B N 0.13166(18) 0.36321(15) 1.16032(12) 0.0530(4) Uani 1 1 d . . . H1B H 0.149(2) 0.4219(18) 1.1104(15) 0.067(7) Uiso 1 1 d . . . C1B C 0.0368(2) 0.36856(17) 1.23228(14) 0.0524(5) Uani 1 1 d . . . C2B C 0.0591(2) 0.26109(16) 1.29679(14) 0.0539(5) Uani 1 1 d . . . H2B H 0.0088 0.2406 1.3531 0.065 Uiso 1 1 calc R . . C3B C 0.1698(2) 0.18729(16) 1.26417(13) 0.0486(5) Uani 1 1 d . . . C4B C 0.2155(2) 0.25444(16) 1.17845(13) 0.0500(5) Uani 1 1 d . . . C5B C 0.3336(2) 0.23547(18) 1.11366(14) 0.0558(5) Uani 1 1 d . . . C6B C 0.5442(3) 0.1038(2) 1.08624(17) 0.0836(8) Uani 1 1 d . . . H6B1 H 0.6071 0.1496 1.0820 0.100 Uiso 1 1 calc R . . H6B2 H 0.5201 0.1185 1.0251 0.100 Uiso 1 1 calc R . . C7B C 0.6156(4) -0.0174(3) 1.1312(2) 0.1285(14) Uani 1 1 d . . . H7B1 H 0.6369 -0.0312 1.1921 0.193 Uiso 1 1 calc R . . H7B2 H 0.7029 -0.0376 1.0970 0.193 Uiso 1 1 calc R . . H7B3 H 0.5534 -0.0619 1.1336 0.193 Uiso 1 1 calc R . . C11B C -0.0687(2) 0.47192(17) 1.23561(15) 0.0545(5) Uani 1 1 d . . . C12B C -0.1290(2) 0.55807(19) 1.15813(17) 0.0676(6) Uani 1 1 d . . . H12B H -0.1011 0.5518 1.1012 0.081 Uiso 1 1 calc R . . C13B C -0.2302(3) 0.6532(2) 1.1647(2) 0.0820(8) Uani 1 1 d . . . H13B H -0.2699 0.7103 1.1122 0.098 Uiso 1 1 calc R . . C14B C -0.2724(3) 0.6639(2) 1.2479(2) 0.0859(8) Uani 1 1 d . . . H14B H -0.3403 0.7280 1.2520 0.103 Uiso 1 1 calc R . . C15B C -0.2140(3) 0.5795(2) 1.32517(19) 0.0820(8) Uani 1 1 d . . . H15B H -0.2425 0.5864 1.3819 0.098 Uiso 1 1 calc R . . C16B C -0.1133(3) 0.48461(19) 1.31909(16) 0.0699(6) Uani 1 1 d . . . H16B H -0.0744 0.4280 1.3720 0.084 Uiso 1 1 calc R . . C31B C 0.2165(2) 0.06493(16) 1.31551(13) 0.0490(5) Uani 1 1 d . . . C32B C 0.2175(2) 0.02537(17) 1.41046(14) 0.0569(5) Uani 1 1 d . . . H32B H 0.1923 0.0773 1.4397 0.068 Uiso 1 1 calc R . . C33B C 0.2545(2) -0.08772(18) 1.46253(14) 0.0622(6) Uani 1 1 d . . . H33B H 0.2545 -0.1101 1.5257 0.075 Uiso 1 1 calc R . . C34B C 0.2920(2) -0.16928(17) 1.42245(14) 0.0581(5) Uani 1 1 d . . . C35B C 0.2904(2) -0.13022(17) 1.32732(15) 0.0591(5) Uani 1 1 d . . . H35B H 0.3149 -0.1820 1.2980 0.071 Uiso 1 1 calc R . . C36B C 0.2535(2) -0.01669(17) 1.27598(14) 0.0554(5) Uani 1 1 d . . . H36B H 0.2533 0.0059 1.2128 0.067 Uiso 1 1 calc R . . N34B N 0.3253(3) -0.28362(16) 1.47479(14) 0.0844(7) Uani 1 1 d . . . C37B C 0.3629(3) -0.3219(2) 1.56698(16) 0.0828(8) Uani 1 1 d . . . H37G H 0.4351 -0.2882 1.5696 0.124 Uiso 0.74(3) 1 calc PR . . H37H H 0.3992 -0.4024 1.5894 0.124 Uiso 0.74(3) 1 calc PR . . H37I H 0.2798 -0.3008 1.6040 0.124 Uiso 0.74(3) 1 calc PR . . H37J H 0.3077 -0.3727 1.6057 0.124 Uiso 0.26(3) 1 calc PR . . H37K H 0.3435 -0.2586 1.5859 0.124 Uiso 0.26(3) 1 calc PR . . H37L H 0.4629 -0.3602 1.5713 0.124 Uiso 0.26(3) 1 calc PR . . C38B C 0.3543(3) -0.36498(19) 1.43194(19) 0.0867(8) Uani 1 1 d . . . H38G H 0.2793 -0.3458 1.3922 0.130 Uiso 0.88(3) 1 calc PR . . H38H H 0.3590 -0.4383 1.4778 0.130 Uiso 0.88(3) 1 calc PR . . H38I H 0.4440 -0.3655 1.3970 0.130 Uiso 0.88(3) 1 calc PR . . H38J H 0.4422 -0.4206 1.4525 0.130 Uiso 0.12(3) 1 calc PR . . H38K H 0.3625 -0.3281 1.3669 0.130 Uiso 0.12(3) 1 calc PR . . H38L H 0.2775 -0.4008 1.4477 0.130 Uiso 0.12(3) 1 calc PR . . 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 O1A 0.0828(11) 0.0546(9) 0.0694(10) -0.0173(8) 0.0210(9) -0.0155(8) O2A 0.0760(10) 0.0497(9) 0.0580(9) -0.0182(7) 0.0085(8) -0.0061(8) N1A 0.0594(11) 0.0511(11) 0.0548(11) -0.0153(9) 0.0049(9) -0.0117(9) C1A 0.0527(12) 0.0585(13) 0.0502(12) -0.0183(10) -0.0009(10) -0.0115(10) C2A 0.0506(12) 0.0646(14) 0.0527(12) -0.0142(11) -0.0006(10) -0.0150(11) C3A 0.0497(12) 0.0570(13) 0.0515(12) -0.0161(10) -0.0038(10) -0.0136(10) C4A 0.0529(12) 0.0512(13) 0.0553(12) -0.0175(10) -0.0004(10) -0.0115(10) C5A 0.0615(13) 0.0496(13) 0.0514(12) -0.0162(10) -0.0013(10) -0.0118(11) C6A 0.0680(15) 0.0709(16) 0.0635(14) -0.0319(12) -0.0005(12) -0.0028(12) C7A 0.117(2) 0.0774(19) 0.098(2) -0.0393(16) -0.0031(18) 0.0184(17) C11A 0.0515(12) 0.0609(14) 0.0510(11) -0.0219(10) -0.0030(10) -0.0100(11) C12A 0.0631(14) 0.0660(16) 0.0687(14) -0.0185(12) 0.0132(12) -0.0093(12) C13A 0.0759(17) 0.0592(15) 0.0764(16) -0.0196(12) 0.0124(13) -0.0098(13) C14A 0.0638(15) 0.0707(16) 0.0706(15) -0.0344(13) -0.0034(12) -0.0028(12) C15A 0.0582(14) 0.0831(18) 0.0790(16) -0.0404(14) 0.0101(12) -0.0183(13) C16A 0.0599(14) 0.0657(15) 0.0710(14) -0.0293(12) 0.0052(12) -0.0179(12) C31A 0.0508(12) 0.0547(13) 0.0496(11) -0.0147(10) -0.0034(9) -0.0158(10) C32A 0.0441(11) 0.0623(14) 0.0649(13) -0.0166(11) -0.0037(10) -0.0132(10) C33A 0.0501(13) 0.0631(14) 0.0682(14) -0.0126(11) 0.0013(11) -0.0245(11) C34A 0.0520(13) 0.0593(13) 0.0546(12) -0.0149(10) -0.0003(10) -0.0168(11) C35A 0.0443(11) 0.0640(14) 0.0570(12) -0.0141(11) -0.0026(10) -0.0132(10) C36A 0.0472(12) 0.0636(14) 0.0528(12) -0.0116(10) -0.0003(9) -0.0215(10) N34A 0.0572(12) 0.0578(12) 0.0883(14) -0.0035(10) 0.0001(10) -0.0125(10) C37A 0.0872(19) 0.0634(16) 0.102(2) -0.0121(14) 0.0115(16) -0.0281(15) C38A 0.0782(18) 0.0690(16) 0.0895(18) -0.0152(14) 0.0104(15) -0.0042(14) O1B 0.0927(12) 0.0615(10) 0.0541(9) -0.0073(8) 0.0150(9) -0.0020(9) O2B 0.0695(10) 0.0563(9) 0.0604(9) -0.0136(7) 0.0131(8) -0.0004(8) N1B 0.0542(10) 0.0464(11) 0.0523(10) -0.0149(8) -0.0008(9) -0.0094(9) C1B 0.0479(12) 0.0522(13) 0.0580(12) -0.0225(10) 0.0011(10) -0.0126(10) C2B 0.0544(12) 0.0486(12) 0.0567(12) -0.0180(10) 0.0052(10) -0.0161(10) C3B 0.0465(11) 0.0485(12) 0.0526(11) -0.0190(9) -0.0040(9) -0.0132(9) C4B 0.0510(12) 0.0467(12) 0.0497(11) -0.0179(9) -0.0043(9) -0.0074(10) C5B 0.0622(14) 0.0506(13) 0.0478(12) -0.0173(10) -0.0026(10) -0.0059(11) C6B 0.0814(18) 0.0705(17) 0.0736(15) -0.0244(13) 0.0212(14) 0.0004(14) C7B 0.132(3) 0.085(2) 0.110(2) -0.0291(18) 0.030(2) 0.027(2) C11B 0.0466(12) 0.0487(12) 0.0667(13) -0.0208(10) 0.0031(10) -0.0136(10) C12B 0.0602(14) 0.0630(15) 0.0754(15) -0.0247(12) -0.0042(12) -0.0100(12) C13B 0.0669(16) 0.0623(16) 0.095(2) -0.0179(14) -0.0060(14) 0.0012(13) C14B 0.0688(16) 0.0609(16) 0.109(2) -0.0311(16) 0.0212(16) -0.0032(13) C15B 0.0858(18) 0.0624(16) 0.0841(17) -0.0294(14) 0.0289(15) -0.0138(14) C16B 0.0745(16) 0.0537(14) 0.0686(15) -0.0169(11) 0.0141(12) -0.0149(12) C31B 0.0466(11) 0.0470(12) 0.0525(12) -0.0159(9) -0.0041(9) -0.0128(9) C32B 0.0659(14) 0.0517(13) 0.0561(12) -0.0226(10) 0.0006(10) -0.0172(11) C33B 0.0786(16) 0.0582(14) 0.0501(12) -0.0150(11) -0.0063(11) -0.0227(12) C34B 0.0604(13) 0.0511(13) 0.0615(13) -0.0149(11) -0.0113(11) -0.0154(10) C35B 0.0669(14) 0.0499(13) 0.0659(14) -0.0264(11) -0.0084(11) -0.0129(11) C36B 0.0594(13) 0.0547(13) 0.0519(12) -0.0191(10) -0.0070(10) -0.0127(10) N34B 0.1227(19) 0.0484(12) 0.0764(14) -0.0113(10) -0.0349(13) -0.0135(12) C37B 0.0947(19) 0.0651(16) 0.0732(16) -0.0002(13) -0.0125(14) -0.0278(14) C38B 0.102(2) 0.0502(14) 0.0956(19) -0.0203(13) -0.0111(16) -0.0069(14) _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 O1A C5A 1.214(2) . ? O2A C5A 1.331(2) . ? O2A C6A 1.446(3) . ? N1A C1A 1.361(3) . ? N1A C4A 1.375(3) . ? C1A C2A 1.378(3) . ? C1A C11A 1.462(3) . ? C2A C3A 1.407(3) . ? C3A C4A 1.394(3) . ? C3A C31A 1.486(3) . ? C4A C5A 1.452(3) . ? C6A C7A 1.488(3) . ? C11A C12A 1.387(3) . ? C11A C16A 1.382(3) . ? C12A C13A 1.380(3) . ? C13A C14A 1.369(3) . ? C14A C15A 1.369(3) . ? C15A C16A 1.375(3) . ? C31A C32A 1.395(3) . ? C31A C36A 1.389(3) . ? C32A C33A 1.376(3) . ? C33A C34A 1.396(3) . ? C34A N34A 1.389(3) . ? C34A C35A 1.395(3) . ? C35A C36A 1.383(3) . ? N34A C37A 1.437(3) . ? N34A C38A 1.421(3) . ? N1A H1A 0.92(2) . ? C2A H2A 0.9300 . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C7A H7A1 0.9600 . ? C7A H7A2 0.9600 . ? C7A H7A3 0.9600 . ? C12A H12A 0.9300 . ? C13A H13A 0.9300 . ? C14A H14A 0.9300 . ? C15A H15A 0.9300 . ? C16A H16A 0.9300 . ? C32A H32A 0.9300 . ? C33A H33A 0.9300 . ? C35A H35A 0.9300 . ? C36A H36A 0.9300 . ? C37A H37A 0.9600 . ? C37A H37B 0.9600 . ? C37A H37C 0.9600 . ? C38A H38A 0.9600 . ? C38A H38B 0.9600 . ? C38A H38C 0.9600 . ? C38A H38D 0.9600 . ? C38A H38E 0.9600 . ? C38A H38F 0.9600 . ? O1B C5B 1.207(2) . ? O2B C5B 1.334(2) . ? O2B C6B 1.444(3) . ? N1B C1B 1.361(3) . ? N1B C4B 1.378(2) . ? C1B C2B 1.379(3) . ? C1B C11B 1.467(3) . ? C2B C3B 1.408(3) . ? C3B C4B 1.399(3) . ? C3B C31B 1.477(3) . ? C4B C5B 1.449(3) . ? C6B C7B 1.484(3) . ? C11B C16B 1.385(3) . ? C11B C12B 1.387(3) . ? C12B C13B 1.384(3) . ? C13B C14B 1.368(4) . ? C14B C15B 1.370(4) . ? C15B C16B 1.377(3) . ? C31B C36B 1.388(3) . ? C31B C32B 1.394(3) . ? C32B C33B 1.376(3) . ? C33B C34B 1.393(3) . ? C34B N34B 1.390(3) . ? C34B C35B 1.397(3) . ? C35B C36B 1.378(3) . ? N34B C37B 1.426(3) . ? N34B C38B 1.430(3) . ? N1B H1B 0.91(2) . ? C2B H2B 0.9300 . ? C6B H6B1 0.9700 . ? C6B H6B2 0.9700 . ? C7B H7B1 0.9600 . ? C7B H7B2 0.9600 . ? C7B H7B3 0.9600 . ? C12B H12B 0.9300 . ? C13B H13B 0.9300 . ? C14B H14B 0.9300 . ? C15B H15B 0.9300 . ? C16B H16B 0.9300 . ? C32B H32B 0.9300 . ? C33B H33B 0.9300 . ? C35B H35B 0.9300 . ? C36B H36B 0.9300 . ? C37B H37G 0.9600 . ? C37B H37H 0.9600 . ? C37B H37I 0.9600 . ? C37B H37J 0.9600 . ? C37B H37K 0.9600 . ? C37B H37L 0.9600 . ? C38B H38G 0.9600 . ? C38B H38H 0.9600 . ? C38B H38I 0.9600 . ? C38B H38J 0.9600 . ? C38B H38K 0.9600 . ? C38B H38L 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 C5A O2A C6A 116.29(17) . . ? C1A N1A C4A 110.34(18) . . ? N1A C1A C2A 106.50(18) . . ? N1A C1A C11A 124.08(19) . . ? C2A C1A C11A 129.3(2) . . ? C1A C2A C3A 109.72(19) . . ? C4A C3A C2A 105.53(18) . . ? C4A C3A C31A 131.48(19) . . ? C2A C3A C31A 122.91(18) . . ? N1A C4A C3A 107.90(18) . . ? N1A C4A C5A 116.73(18) . . ? C3A C4A C5A 135.3(2) . . ? O1A C5A O2A 122.68(19) . . ? O1A C5A C4A 123.93(19) . . ? O2A C5A C4A 113.38(18) . . ? O2A C6A C7A 106.3(2) . . ? C16A C11A C12A 117.2(2) . . ? C16A C11A C1A 120.4(2) . . ? C12A C11A C1A 122.4(2) . . ? C13A C12A C11A 121.2(2) . . ? C13A C12A H12A 119.4 . . ? C11A C12A H12A 119.4 . . ? C14A C13A C12A 120.3(2) . . ? C14A C13A H13A 119.8 . . ? C12A C13A H13A 119.8 . . ? C15A C14A C13A 119.3(2) . . ? C15A C14A H14A 120.3 . . ? C13A C14A H14A 120.3 . . ? C14A C15A C16A 120.4(2) . . ? C14A C15A H15A 119.8 . . ? C16A C15A H15A 119.8 . . ? C15A C16A C11A 121.5(2) . . ? C15A C16A H16A 119.2 . . ? C11A C16A H16A 119.2 . . ? C36A C31A C32A 116.16(19) . . ? C36A C31A C3A 124.19(18) . . ? C32A C31A C3A 119.52(18) . . ? C33A C32A C31A 122.5(2) . . ? C33A C32A H32A 118.8 . . ? C31A C32A H32A 118.8 . . ? C32A C33A C34A 121.0(2) . . ? C32A C33A H33A 119.5 . . ? C34A C33A H33A 119.5 . . ? N34A C34A C35A 121.55(19) . . ? N34A C34A C33A 121.46(19) . . ? C35A C34A C33A 116.99(19) . . ? C36A C35A C34A 121.2(2) . . ? C36A C35A H35A 119.4 . . ? C34A C35A H35A 119.4 . . ? C35A C36A C31A 122.08(19) . . ? C35A C36A H36A 119.0 . . ? C31A C36A H36A 119.0 . . ? C34A N34A C38A 121.21(19) . . ? C34A N34A C37A 120.2(2) . . ? C38A N34A C37A 118.6(2) . . ? C1A N1A H1A 126.6(14) . . ? C4A N1A H1A 123.0(14) . . ? C1A C2A H2A 125.1 . . ? C3A C2A H2A 125.1 . . ? O2A C6A H6A1 110.5 . . ? C7A C6A H6A1 110.5 . . ? O2A C6A H6A2 110.5 . . ? C7A C6A H6A2 110.5 . . ? H6A1 C6A H6A2 108.7 . . ? C6A C7A H7A1 109.5 . . ? C6A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C6A C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? N34A C37A H37A 109.5 . . ? N34A C37A H37B 109.5 . . ? H37A C37A H37B 109.5 . . ? N34A C37A H37C 109.5 . . ? H37A C37A H37C 109.5 . . ? H37B C37A H37C 109.5 . . ? N34A C38A H38A 109.5 . . ? N34A C38A H38B 109.5 . . ? H38A C38A H38B 109.5 . . ? N34A C38A H38C 109.5 . . ? H38A C38A H38C 109.5 . . ? H38B C38A H38C 109.5 . . ? N34A C38A H38D 109.5 . . ? H38A C38A H38D 141.1 . . ? H38B C38A H38D 56.3 . . ? H38C C38A H38D 56.3 . . ? N34A C38A H38E 109.5 . . ? H38A C38A H38E 56.3 . . ? H38B C38A H38E 141.1 . . ? H38C C38A H38E 56.3 . . ? H38D C38A H38E 109.5 . . ? N34A C38A H38F 109.5 . . ? H38A C38A H38F 56.3 . . ? H38B C38A H38F 56.3 . . ? H38C C38A H38F 141.1 . . ? H38D C38A H38F 109.5 . . ? H38E C38A H38F 109.5 . . ? C5B O2B C6B 117.62(17) . . ? C1B N1B C4B 109.87(17) . . ? N1B C1B C2B 107.14(17) . . ? N1B C1B C11B 124.16(18) . . ? C2B C1B C11B 128.68(19) . . ? C1B C2B C3B 109.35(18) . . ? C4B C3B C2B 105.62(17) . . ? C4B C3B C31B 131.34(18) . . ? C2B C3B C31B 123.03(17) . . ? N1B C4B C3B 107.99(17) . . ? N1B C4B C5B 117.40(18) . . ? C3B C4B C5B 134.32(18) . . ? O1B C5B O2B 122.49(19) . . ? O1B C5B C4B 124.76(19) . . ? O2B C5B C4B 112.75(17) . . ? O2B C6B C7B 107.1(2) . . ? C16B C11B C12B 117.8(2) . . ? C16B C11B C1B 119.5(2) . . ? C12B C11B C1B 122.7(2) . . ? C13B C12B C11B 120.7(2) . . ? C13B C12B H12B 119.6 . . ? C11B C12B H12B 119.6 . . ? C14B C13B C12B 120.4(2) . . ? C14B C13B H13B 119.8 . . ? C12B C13B H13B 119.8 . . ? C13B C14B C15B 119.6(2) . . ? C13B C14B H14B 120.2 . . ? C15B C14B H14B 120.2 . . ? C14B C15B C16B 120.2(2) . . ? C14B C15B H15B 119.9 . . ? C16B C15B H15B 119.9 . . ? C15B C16B C11B 121.2(2) . . ? C15B C16B H16B 119.4 . . ? C11B C16B H16B 119.4 . . ? C36B C31B C32B 116.06(18) . . ? C36B C31B C3B 124.27(18) . . ? C32B C31B C3B 119.58(18) . . ? C33B C32B C31B 122.43(19) . . ? C33B C32B H32B 118.8 . . ? C31B C32B H32B 118.8 . . ? C32B C33B C34B 121.2(2) . . ? C32B C33B H33B 119.4 . . ? C34B C33B H33B 119.4 . . ? N34B C34B C33B 121.6(2) . . ? N34B C34B C35B 121.8(2) . . ? C33B C34B C35B 116.62(19) . . ? C36B C35B C34B 121.53(19) . . ? C36B C35B H35B 119.2 . . ? C34B C35B H35B 119.2 . . ? C35B C36B C31B 122.11(19) . . ? C35B C36B H36B 118.9 . . ? C31B C36B H36B 118.9 . . ? C34B N34B C37B 120.3(2) . . ? C34B N34B C38B 120.1(2) . . ? C37B N34B C38B 118.1(2) . . ? C1B N1B H1B 127.3(14) . . ? C4B N1B H1B 122.2(14) . . ? C1B C2B H2B 125.3 . . ? C3B C2B H2B 125.3 . . ? O2B C6B H6B1 110.3 . . ? C7B C6B H6B1 110.3 . . ? O2B C6B H6B2 110.3 . . ? C7B C6B H6B2 110.3 . . ? H6B1 C6B H6B2 108.6 . . ? C6B C7B H7B1 109.5 . . ? C6B C7B H7B2 109.5 . . ? H7B1 C7B H7B2 109.5 . . ? C6B C7B H7B3 109.5 . . ? H7B1 C7B H7B3 109.5 . . ? H7B2 C7B H7B3 109.5 . . ? N34B C37B H37G 109.5 . . ? N34B C37B H37H 109.5 . . ? H37G C37B H37H 109.5 . . ? N34B C37B H37I 109.5 . . ? H37G C37B H37I 109.5 . . ? H37H C37B H37I 109.5 . . ? N34B C37B H37J 109.5 . . ? H37G C37B H37J 141.1 . . ? H37H C37B H37J 56.3 . . ? H37I C37B H37J 56.3 . . ? N34B C37B H37K 109.5 . . ? H37G C37B H37K 56.3 . . ? H37H C37B H37K 141.1 . . ? H37I C37B H37K 56.3 . . ? H37J C37B H37K 109.5 . . ? N34B C37B H37L 109.5 . . ? H37G C37B H37L 56.3 . . ? H37H C37B H37L 56.3 . . ? H37I C37B H37L 141.1 . . ? H37J C37B H37L 109.5 . . ? H37K C37B H37L 109.5 . . ? N34B C38B H38G 109.5 . . ? N34B C38B H38H 109.5 . . ? H38G C38B H38H 109.5 . . ? N34B C38B H38I 109.5 . . ? H38G C38B H38I 109.5 . . ? H38H C38B H38I 109.5 . . ? N34B C38B H38J 109.5 . . ? H38G C38B H38J 141.1 . . ? H38H C38B H38J 56.3 . . ? H38I C38B H38J 56.3 . . ? N34B C38B H38K 109.5 . . ? H38G C38B H38K 56.3 . . ? H38H C38B H38K 141.1 . . ? H38I C38B H38K 56.3 . . ? H38J C38B H38K 109.5 . . ? N34B C38B H38L 109.5 . . ? H38G C38B H38L 56.3 . . ? H38H C38B H38L 56.3 . . ? H38I C38B H38L 141.1 . . ? H38J C38B H38L 109.5 . . ? H38K C38B H38L 109.5 . . ? 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 C4A N1A C1A C2A -0.4(2) . . . . ? C4A N1A C1A C11A -177.63(19) . . . . ? N1A C1A C2A C3A -0.3(2) . . . . ? C11A C1A C2A C3A 176.7(2) . . . . ? C1A C2A C3A C4A 0.8(2) . . . . ? C1A C2A C3A C31A -176.37(18) . . . . ? C1A N1A C4A C3A 1.0(2) . . . . ? C1A N1A C4A C5A -176.91(18) . . . . ? C2A C3A C4A N1A -1.1(2) . . . . ? C31A C3A C4A N1A 175.8(2) . . . . ? C2A C3A C4A C5A 176.2(2) . . . . ? C31A C3A C4A C5A -6.9(4) . . . . ? C6A O2A C5A O1A -5.9(3) . . . . ? C6A O2A C5A C4A 175.04(18) . . . . ? N1A C4A C5A O1A -9.9(3) . . . . ? C3A C4A C5A O1A 173.0(2) . . . . ? N1A C4A C5A O2A 169.13(18) . . . . ? C3A C4A C5A O2A -8.0(3) . . . . ? C5A O2A C6A C7A 179.8(2) . . . . ? N1A C1A C11A C16A -165.7(2) . . . . ? C2A C1A C11A C16A 17.8(3) . . . . ? N1A C1A C11A C12A 15.9(3) . . . . ? C2A C1A C11A C12A -160.6(2) . . . . ? C16A C11A C12A C13A 0.1(3) . . . . ? C1A C11A C12A C13A 178.6(2) . . . . ? C11A C12A C13A C14A 0.0(4) . . . . ? C12A C13A C14A C15A 0.1(4) . . . . ? C13A C14A C15A C16A -0.4(4) . . . . ? C14A C15A C16A C11A 0.5(4) . . . . ? C12A C11A C16A C15A -0.4(3) . . . . ? C1A C11A C16A C15A -178.9(2) . . . . ? C4A C3A C31A C36A -32.9(3) . . . . ? C2A C3A C31A C36A 143.5(2) . . . . ? C4A C3A C31A C32A 151.4(2) . . . . ? C2A C3A C31A C32A -32.1(3) . . . . ? C36A C31A C32A C33A 1.8(3) . . . . ? C3A C31A C32A C33A 177.8(2) . . . . ? C31A C32A C33A C34A -0.3(3) . . . . ? C32A C33A C34A N34A 179.7(2) . . . . ? C32A C33A C34A C35A -1.0(3) . . . . ? N34A C34A C35A C36A -179.9(2) . . . . ? C33A C34A C35A C36A 0.9(3) . . . . ? C34A C35A C36A C31A 0.6(3) . . . . ? C32A C31A C36A C35A -1.9(3) . . . . ? C3A C31A C36A C35A -177.70(19) . . . . ? C35A C34A N34A C38A 7.1(3) . . . . ? C33A C34A N34A C38A -173.7(2) . . . . ? C35A C34A N34A C37A -174.9(2) . . . . ? C33A C34A N34A C37A 4.4(4) . . . . ? C4B N1B C1B C2B -0.9(2) . . . . ? C4B N1B C1B C11B -179.91(18) . . . . ? N1B C1B C2B C3B -0.2(2) . . . . ? C11B C1B C2B C3B 178.7(2) . . . . ? C1B C2B C3B C4B 1.2(2) . . . . ? C1B C2B C3B C31B -177.69(18) . . . . ? C1B N1B C4B C3B 1.7(2) . . . . ? C1B N1B C4B C5B -173.09(17) . . . . ? C2B C3B C4B N1B -1.7(2) . . . . ? C31B C3B C4B N1B 177.02(19) . . . . ? C2B C3B C4B C5B 171.8(2) . . . . ? C31B C3B C4B C5B -9.5(4) . . . . ? C6B O2B C5B O1B 4.6(3) . . . . ? C6B O2B C5B C4B -174.8(2) . . . . ? N1B C4B C5B O1B -5.3(3) . . . . ? C3B C4B C5B O1B -178.3(2) . . . . ? N1B C4B C5B O2B 173.98(18) . . . . ? C3B C4B C5B O2B 0.9(3) . . . . ? C5B O2B C6B C7B -179.7(2) . . . . ? N1B C1B C11B C16B -150.7(2) . . . . ? C2B C1B C11B C16B 30.5(3) . . . . ? N1B C1B C11B C12B 30.5(3) . . . . ? C2B C1B C11B C12B -148.2(2) . . . . ? C16B C11B C12B C13B 0.0(3) . . . . ? C1B C11B C12B C13B 178.8(2) . . . . ? C11B C12B C13B C14B 0.1(4) . . . . ? C12B C13B C14B C15B -0.1(4) . . . . ? C13B C14B C15B C16B 0.1(4) . . . . ? C14B C15B C16B C11B 0.0(4) . . . . ? C12B C11B C16B C15B 0.0(3) . . . . ? C1B C11B C16B C15B -178.8(2) . . . . ? C4B C3B C31B C36B -38.3(3) . . . . ? C2B C3B C31B C36B 140.2(2) . . . . ? C4B C3B C31B C32B 145.3(2) . . . . ? C2B C3B C31B C32B -36.1(3) . . . . ? C36B C31B C32B C33B 0.7(3) . . . . ? C3B C31B C32B C33B 177.41(19) . . . . ? C31B C32B C33B C34B -0.6(3) . . . . ? C32B C33B C34B N34B -178.0(2) . . . . ? C32B C33B C34B C35B 0.2(3) . . . . ? N34B C34B C35B C36B 178.2(2) . . . . ? C33B C34B C35B C36B -0.1(3) . . . . ? C34B C35B C36B C31B 0.3(3) . . . . ? C32B C31B C36B C35B -0.6(3) . . . . ? C3B C31B C36B C35B -177.09(19) . . . . ? C33B C34B N34B C37B -18.5(4) . . . . ? C35B C34B N34B C37B 163.4(2) . . . . ? C33B C34B N34B C38B 176.0(2) . . . . ? C35B C34B N34B C38B -2.2(4) . . . . ? 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 N1A H1A O1B 0.92(2) 2.15(2) 3.068(2) 174(2) . N1B H1B O1A 0.91(2) 2.09(2) 2.995(2) 176(2) . C12A H12A O1B 0.93 2.57 3.445(3) 157.0 . C12B H12B O1A 0.93 2.96 3.616(3) 128.7 . C36A H36A O2A 0.93 2.44 2.932(2) 112.9 . C36B H36B O2B 0.93 2.47 2.910(3) 108.7 . #============================================================ data_(IIIa) _database_code_depnum_ccdc_archive 'CCDC 233395' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-(4-Dimethylamino-2,6-dimethyl-phenyl)-5-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester ; _chemical_name_common ; 3-(4-Dimethylamino-2,6-dimethyl-phenyl)-5-phenyl-1H-pyrrole-2- carboxylic acid ethyl ester ; _chemical_melting_point 432 _chemical_formula_moiety 'C23 H26 N2 O2' _chemical_formula_sum 'C23 H26 N2 O2' _chemical_formula_weight 362.46 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' _symmetry_space_group_name_Hall '-p 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.861(2) _cell_length_b 9.401(3) _cell_length_c 14.244(3) _cell_angle_alpha 83.46(2) _cell_angle_beta 81.780(10) _cell_angle_gamma 79.74(2) _cell_volume 1020.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 47 _cell_measurement_theta_min 6.1 _cell_measurement_theta_max 17.2 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 1.00 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'Siemens P4' _diffrn_measurement_method /w _diffrn_standards_number 4 _diffrn_standards_interval_count 296 _diffrn_standards_decay_% 1 _diffrn_reflns_number 4454 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_av_sigmaI/netI 0.045 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.2 _diffrn_reflns_theta_max 25.0 _diffrn_measured_fraction_theta_max 1.00 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_full 1.00 _reflns_number_total 3604 _reflns_number_gt 1979 _reflns_threshold_expression >2\s(I) _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_cell_refinement 'XSCANS (Siemens, 1996)' _computing_data_reduction 'XSCANS (Siemens, 1996)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002), ORTEX (McArdle, 1995)' _computing_publication_material 'PLATON (Spek, 2002), PREP8 (Ferguson, 1998)' _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^)+(0.2P)] 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 0.004(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3604 _refine_ls_number_parameters 261 _refine_ls_number_restraints 32 _refine_ls_R_factor_all 0.214 _refine_ls_R_factor_gt 0.154 _refine_ls_goodness_of_fit_ref 2.111 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.46 _refine_diff_density_min -0.47 _refine_diff_density_rms 0.11 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 0.6360(8) 0.4969(7) 0.3971(4) 0.081(2) Uani 1 1 d . . . O2 O 0.7259(10) 0.3768(9) 0.2671(5) 0.110(3) Uani 1 1 d D . . N1 N 0.3461(9) 0.3420(7) 0.4343(5) 0.066(2) Uani 1 1 d . A . H1 H 0.3444 0.3954 0.4798 0.080 Uiso 1 1 calc R . . C1 C 0.2223(12) 0.2614(9) 0.4276(6) 0.068(2) Uani 1 1 d . . . C2 C 0.2768(12) 0.1885(9) 0.3475(6) 0.069(2) Uani 1 1 d . . . H2 H 0.2190 0.1222 0.3265 0.083 Uiso 1 1 calc R . . C3 C 0.4340(12) 0.2299(9) 0.3023(6) 0.067(2) Uani 1 1 d . A . C4 C 0.4765(11) 0.3262(9) 0.3573(6) 0.064(2) Uani 1 1 d . . . C5 C 0.6161(12) 0.4076(10) 0.3458(6) 0.070(2) Uani 1 1 d . A . C6A C 0.845(3) 0.487(2) 0.2341(14) 0.071(6) Uani 0.50 1 d PDU A -1 H6A H 0.7910 0.5814 0.2546 0.085 Uiso 0.50 1 calc PR A -1 H6B H 0.9543 0.4580 0.2605 0.085 Uiso 0.50 1 calc PR A -1 C7A C 0.876(3) 0.494(3) 0.1277(13) 0.095(6) Uani 0.50 1 d PDU A -1 H7A H 0.9714 0.5452 0.1048 0.143 Uiso 0.50 1 calc PR A -1 H7B H 0.7731 0.5441 0.1019 0.143 Uiso 0.50 1 calc PR A -1 H7C H 0.9037 0.3974 0.1081 0.143 Uiso 0.50 1 calc PR A -1 C6B C 0.892(2) 0.426(3) 0.2425(17) 0.084(7) Uani 0.50 1 d PDU A -2 H6C H 0.9804 0.3509 0.2147 0.100 Uiso 0.50 1 calc PR A -2 H6D H 0.9320 0.4555 0.2975 0.100 Uiso 0.50 1 calc PR A -2 C7B C 0.848(4) 0.555(3) 0.169(2) 0.131(9) Uani 0.50 1 d PDU A -2 H7D H 0.7601 0.5355 0.1342 0.196 Uiso 0.50 1 calc PR A -2 H7E H 0.9503 0.5688 0.1266 0.196 Uiso 0.50 1 calc PR A -2 H7F H 0.8042 0.6404 0.2019 0.196 Uiso 0.50 1 calc PR A -2 N34 N 0.7827(13) 0.0248(10) -0.0486(6) 0.099(3) Uani 1 1 d . . . C11 C 0.0610(12) 0.2613(9) 0.4940(6) 0.068(2) Uani 1 1 d . . . C12 C 0.0301(13) 0.3364(11) 0.5750(7) 0.081(3) Uani 1 1 d . . . H12 H 0.1122 0.3889 0.5883 0.097 Uiso 1 1 calc R . . C13 C -0.1228(14) 0.3328(11) 0.6355(7) 0.091(3) Uani 1 1 d . . . H13 H -0.1429 0.3828 0.6898 0.109 Uiso 1 1 calc R . . C14 C -0.2450(14) 0.2570(11) 0.6170(7) 0.084(3) Uani 1 1 d . . . H14 H -0.3466 0.2544 0.6591 0.101 Uiso 1 1 calc R . . C15 C -0.2182(14) 0.1843(12) 0.5361(8) 0.091(3) Uani 1 1 d . . . H15 H -0.3030 0.1355 0.5219 0.109 Uiso 1 1 calc R . . C16 C -0.0656(13) 0.1850(11) 0.4771(7) 0.082(3) Uani 1 1 d . . . H16 H -0.0457 0.1328 0.4239 0.099 Uiso 1 1 calc R . . C31 C 0.5291(12) 0.1771(9) 0.2104(6) 0.065(2) Uani 1 1 d . . . C32 C 0.6423(13) 0.0439(10) 0.2115(6) 0.070(2) Uani 1 1 d . A . C33 C 0.7226(12) -0.0067(10) 0.1233(6) 0.074(3) Uani 1 1 d . . . H33 H 0.7939 -0.0970 0.1233 0.089 Uiso 1 1 calc R A . C34 C 0.6983(12) 0.0740(11) 0.0365(6) 0.077(3) Uani 1 1 d . A . C35 C 0.5864(12) 0.2068(10) 0.0383(6) 0.072(3) Uani 1 1 d . . . H35 H 0.5657 0.2619 -0.0186 0.087 Uiso 1 1 calc R A . C36 C 0.5051(12) 0.2580(9) 0.1241(6) 0.068(2) Uani 1 1 d . A . C37 C 0.6776(15) -0.0442(9) 0.3015(4) 0.102(4) Uani 1 1 d . . . H37A H 0.7093 0.0154 0.3444 0.154 Uiso 1 1 calc R A . H37B H 0.7714 -0.1228 0.2886 0.154 Uiso 1 1 calc R . . H37C H 0.5749 -0.0825 0.3300 0.154 Uiso 1 1 calc R . . C38 C 0.8667(12) -0.1276(8) -0.0507(4) 0.112(4) Uani 1 1 d R . . H38A H 0.9527 -0.1485 -0.0073 0.168 Uiso 1 1 calc R . . H38B H 0.9217 -0.1443 -0.1140 0.168 Uiso 1 1 calc R . . H38C H 0.7805 -0.1895 -0.0321 0.168 Uiso 1 1 calc R . . C39 C 0.7512(11) 0.1020(8) -0.1370(4) 0.125(5) Uani 1 1 d R . . H39A H 0.6289 0.1165 -0.1423 0.187 Uiso 1 1 calc R . . H39B H 0.8146 0.0476 -0.1877 0.187 Uiso 1 1 calc R . . H39C H 0.7889 0.1945 -0.1411 0.187 Uiso 1 1 calc R . . C40 C 0.3858(15) 0.4058(10) 0.1212(7) 0.087(3) Uani 1 1 d . . . H40A H 0.2817 0.3998 0.1647 0.130 Uiso 1 1 calc R A . H40B H 0.3558 0.4329 0.0578 0.130 Uiso 1 1 calc R . . H40C H 0.4452 0.4774 0.1391 0.130 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 0.088(5) 0.095(4) 0.070(4) -0.031(4) 0.000(3) -0.036(4) O2 0.113(6) 0.163(7) 0.072(4) -0.052(5) 0.028(4) -0.078(5) N1 0.072(5) 0.078(4) 0.053(4) -0.020(3) -0.001(3) -0.019(4) C1 0.081(6) 0.067(5) 0.057(5) -0.001(4) 0.000(4) -0.026(4) C2 0.085(6) 0.065(5) 0.062(5) -0.008(4) -0.007(5) -0.028(5) C3 0.079(6) 0.072(5) 0.055(5) -0.018(4) -0.002(4) -0.022(4) C4 0.065(5) 0.075(5) 0.055(5) -0.011(4) -0.005(4) -0.016(4) C5 0.075(6) 0.085(6) 0.052(5) -0.012(4) 0.002(4) -0.027(5) C6A 0.061(9) 0.081(10) 0.070(8) -0.010(8) -0.004(7) -0.013(8) C7A 0.105(10) 0.102(10) 0.078(8) -0.009(8) -0.011(8) -0.016(8) C6B 0.077(10) 0.094(10) 0.087(10) -0.029(7) -0.010(8) -0.020(8) C7B 0.136(13) 0.120(11) 0.136(12) 0.000(8) -0.020(9) -0.026(9) N34 0.117(7) 0.110(7) 0.070(5) -0.033(5) 0.015(5) -0.026(6) C11 0.079(6) 0.067(5) 0.056(5) 0.002(4) -0.003(4) -0.018(4) C12 0.081(6) 0.094(6) 0.069(6) -0.025(5) 0.014(5) -0.029(5) C13 0.090(7) 0.100(7) 0.078(7) -0.022(5) 0.024(6) -0.024(6) C14 0.077(6) 0.098(7) 0.074(6) 0.009(5) 0.001(5) -0.025(6) C15 0.080(7) 0.116(8) 0.080(7) 0.000(6) -0.004(6) -0.036(6) C16 0.088(7) 0.089(6) 0.072(6) -0.011(5) 0.006(5) -0.034(6) C31 0.081(6) 0.070(5) 0.048(5) -0.009(4) -0.010(4) -0.023(5) C32 0.088(6) 0.075(6) 0.051(5) -0.006(4) -0.012(4) -0.022(5) C33 0.082(6) 0.079(6) 0.066(6) -0.027(5) -0.002(5) -0.019(5) C34 0.076(6) 0.105(7) 0.058(5) -0.032(5) 0.005(5) -0.027(5) C35 0.076(6) 0.092(6) 0.053(5) -0.016(4) -0.005(4) -0.025(5) C36 0.074(6) 0.075(5) 0.060(5) -0.009(4) -0.006(4) -0.021(5) C37 0.136(10) 0.095(7) 0.069(6) -0.006(5) -0.010(6) -0.003(7) C38 0.105(9) 0.119(9) 0.120(10) -0.065(8) 0.019(7) -0.036(7) C39 0.142(11) 0.171(12) 0.063(7) -0.038(8) 0.006(7) -0.029(10) C40 0.112(8) 0.077(6) 0.068(6) -0.006(5) -0.016(5) -0.005(6) _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 C5 1.217(10) . ? O2 C5 1.340(10) . ? O2 C6A 1.510(15) . ? O2 C6B 1.446(16) . ? N1 C1 1.355(11) . ? N1 C4 1.392(10) . ? C1 C2 1.374(12) . ? C1 C11 1.470(13) . ? C2 C3 1.407(12) . ? C3 C4 1.375(11) . ? C3 C31 1.501(11) . ? C4 C5 1.427(12) . ? C6A C7A 1.50(2) . ? C6B C7B 1.53(2) . ? N34 C34 1.382(11) . ? N34 C38 1.468(12) . ? N34 C39 1.411(12) . ? C11 C16 1.388(13) . ? C11 C12 1.390(12) . ? C12 C13 1.379(13) . ? C13 C14 1.363(14) . ? C14 C15 1.378(14) . ? C15 C16 1.363(13) . ? C31 C32 1.401(12) . ? C31 C36 1.389(12) . ? C32 C33 1.416(11) . ? C32 C37 1.477(11) . ? C33 C34 1.395(13) . ? C34 C35 1.394(13) . ? C35 C36 1.390(12) . ? C36 C40 1.531(12) . ? N1 H1 0.8600 . ? C2 H2 0.9300 . ? C6A H6A 0.9700 . ? C6A H6B 0.9700 . ? C7A H7A 0.9600 . ? C7A H7B 0.9600 . ? C7A H7C 0.9600 . ? C6B H6C 0.9700 . ? C6B H6D 0.9700 . ? C7B H7D 0.9600 . ? C7B H7E 0.9600 . ? C7B H7F 0.9600 . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C33 H33 0.9300 . ? C35 H35 0.9300 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 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 C5 O2 C6B 124.3(11) . . ? C5 O2 C6A 114.0(10) . . ? C1 N1 C4 110.4(7) . . ? N1 C1 C2 106.6(7) . . ? N1 C1 C11 124.2(8) . . ? C2 C1 C11 129.2(8) . . ? C1 C2 C3 109.2(7) . . ? C4 C3 C2 106.8(7) . . ? C4 C3 C31 128.8(8) . . ? C2 C3 C31 124.5(7) . . ? C3 C4 N1 107.0(8) . . ? C3 C4 C5 132.3(8) . . ? N1 C4 C5 120.6(7) . . ? O1 C5 O2 122.3(8) . . ? O1 C5 C4 126.7(8) . . ? O2 C5 C4 110.9(7) . . ? C7A C6A O2 107.1(15) . . ? O2 C6B C7B 101.3(16) . . ? C34 N34 C39 121.6(9) . . ? C34 N34 C38 119.4(8) . . ? C39 N34 C38 116.7(6) . . ? C16 C11 C12 118.0(8) . . ? C16 C11 C1 120.3(8) . . ? C12 C11 C1 121.7(8) . . ? C13 C12 C11 119.7(9) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C14 C13 C12 121.0(10) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 120.1(9) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 119.1(10) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C11 122.0(9) . . ? C15 C16 H16 119.0 . . ? C11 C16 H16 119.0 . . ? C36 C31 C32 119.5(8) . . ? C36 C31 C3 120.8(8) . . ? C32 C31 C3 119.7(7) . . ? C31 C32 C33 118.3(8) . . ? C31 C32 C37 121.8(7) . . ? C33 C32 C37 119.9(8) . . ? C34 C33 C32 122.3(9) . . ? C34 C33 H33 118.8 . . ? C32 C33 H33 118.8 . . ? N34 C34 C35 121.0(9) . . ? N34 C34 C33 121.4(10) . . ? C35 C34 C33 117.6(8) . . ? C36 C35 C34 121.0(9) . . ? C36 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? C31 C36 C35 121.2(8) . . ? C31 C36 C40 120.5(8) . . ? C35 C36 C40 118.3(8) . . ? C1 N1 H1 124.8 . . ? C4 N1 H1 124.8 . . ? C1 C2 H2 125.4 . . ? C3 C2 H2 125.4 . . ? C7A C6A H6A 110.3 . . ? O2 C6A H6A 110.3 . . ? C7A C6A H6B 110.3 . . ? O2 C6A H6B 110.3 . . ? H6A C6A H6B 108.6 . . ? O2 C6B H6C 111.5 . . ? C7B C6B H6C 111.5 . . ? O2 C6B H6D 111.5 . . ? C7B C6B H6D 111.5 . . ? H6C C6B H6D 109.3 . . ? C6B C7B H7D 109.5 . . ? C6B C7B H7E 109.5 . . ? H7D C7B H7E 109.5 . . ? C6B C7B H7F 109.5 . . ? H7D C7B H7F 109.5 . . ? H7E C7B H7F 109.5 . . ? C32 C37 H37A 109.5 . . ? C32 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C32 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? N34 C38 H38A 109.5 . . ? N34 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? N34 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N34 C39 H39A 109.5 . . ? N34 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? N34 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C36 C40 H40A 109.5 . . ? C36 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C36 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? 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 C4 N1 C1 C2 2.4(9) . . . . ? C4 N1 C1 C11 -175.8(8) . . . . ? N1 C1 C2 C3 -2.4(10) . . . . ? C11 C1 C2 C3 175.7(9) . . . . ? C1 C2 C3 C4 1.5(10) . . . . ? C1 C2 C3 C31 -177.5(8) . . . . ? C2 C3 C4 N1 -0.1(10) . . . . ? C31 C3 C4 N1 178.9(8) . . . . ? C2 C3 C4 C5 -177.4(9) . . . . ? C31 C3 C4 C5 1.6(17) . . . . ? C1 N1 C4 C3 -1.5(10) . . . . ? C1 N1 C4 C5 176.2(8) . . . . ? C6B O2 C5 O1 10.7(19) . . . . ? C6A O2 C5 O1 -15.2(17) . . . . ? C6B O2 C5 C4 -171.1(13) . . . . ? C6A O2 C5 C4 163.0(12) . . . . ? C3 C4 C5 O1 175.6(10) . . . . ? N1 C4 C5 O1 -1.4(15) . . . . ? C3 C4 C5 O2 -2.6(15) . . . . ? N1 C4 C5 O2 -179.6(8) . . . . ? C5 O2 C6A C7A -146.8(17) . . . . ? C6B O2 C6A C7A 93(4) . . . . ? C5 O2 C6B C7B -100(2) . . . . ? C6A O2 C6B C7B -28(3) . . . . ? N1 C1 C11 C16 174.5(8) . . . . ? C2 C1 C11 C16 -3.3(14) . . . . ? N1 C1 C11 C12 -5.6(14) . . . . ? C2 C1 C11 C12 176.7(9) . . . . ? C16 C11 C12 C13 0.2(14) . . . . ? C1 C11 C12 C13 -179.8(9) . . . . ? C11 C12 C13 C14 -0.3(16) . . . . ? C12 C13 C14 C15 -1.0(16) . . . . ? C13 C14 C15 C16 2.4(15) . . . . ? C14 C15 C16 C11 -2.5(16) . . . . ? C12 C11 C16 C15 1.2(15) . . . . ? C1 C11 C16 C15 -178.8(9) . . . . ? C4 C3 C31 C36 -83.3(12) . . . . ? C2 C3 C31 C36 95.5(11) . . . . ? C4 C3 C31 C32 97.3(12) . . . . ? C2 C3 C31 C32 -83.8(11) . . . . ? C36 C31 C32 C33 -2.9(13) . . . . ? C3 C31 C32 C33 176.5(8) . . . . ? C36 C31 C32 C37 177.8(9) . . . . ? C3 C31 C32 C37 -2.8(14) . . . . ? C31 C32 C33 C34 2.8(13) . . . . ? C37 C32 C33 C34 -177.9(10) . . . . ? C39 N34 C34 C35 -3.9(15) . . . . ? C38 N34 C34 C35 -166.1(8) . . . . ? C39 N34 C34 C33 176.4(9) . . . . ? C38 N34 C34 C33 14.3(14) . . . . ? C32 C33 C34 N34 177.7(9) . . . . ? C32 C33 C34 C35 -2.0(14) . . . . ? N34 C34 C35 C36 -178.3(8) . . . . ? C33 C34 C35 C36 1.4(13) . . . . ? C32 C31 C36 C35 2.4(13) . . . . ? C3 C31 C36 C35 -176.9(8) . . . . ? C32 C31 C36 C40 -178.4(8) . . . . ? C3 C31 C36 C40 2.3(13) . . . . ? C34 C35 C36 C31 -1.7(13) . . . . ? C34 C35 C36 C40 179.1(8) . . . . ? #================================================================== data_(IIIb) _database_code_depnum_ccdc_archive 'CCDC 233396' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-(4-Dimethylamino-2,6-dimethyl-phenyl)-5-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester ; _chemical_name_common ; 3-(4-Dimethylamino-2,6-dimethyl-phenyl)-5-phenyl-1H-pyrrole-2- carboxylic acid ethyl ester ; _chemical_melting_point 412 _chemical_formula_moiety 'C23 H26 N2 O2' _chemical_formula_sum 'C23 H26 N2 O2' _chemical_formula_weight 362.46 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' _symmetry_space_group_name_Hall '-p 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6973(5) _cell_length_b 9.3729(6) _cell_length_c 14.0807(10) _cell_angle_alpha 83.3470(10) _cell_angle_beta 82.3910(10) _cell_angle_gamma 79.1320(10) _cell_volume 984.54(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9999 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 26.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.944 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker Apex CCD diffractometer' _diffrn_measurement_method '/f and /w' _diffrn_standards_decay_% 1 _diffrn_reflns_number 16869 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.2 _diffrn_reflns_theta_max 28.2 _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 28.22 _diffrn_measured_fraction_theta_full 0.943 _reflns_number_total 4591 _reflns_number_gt 3988 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SAINT/SMART software (Bruker, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett and Johnson, 1996), PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and WordPerfect macro PREP8 (Ferguson, 1998)' _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^)+(0.0678P)^2^+0.2892P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4591 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1326 _refine_ls_wR_factor_gt 0.1273 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.28 _refine_diff_density_min -0.28 _refine_diff_density_rms 0.04 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 0.63881(11) 0.49654(10) 0.39758(6) 0.0387(2) Uani 1 1 d . . . O2 O 0.73146(14) 0.37923(15) 0.26467(7) 0.0648(3) Uani 1 1 d . . . N1 N 0.34801(12) 0.34147(11) 0.43348(7) 0.0304(2) Uani 1 1 d . A . H1 H 0.347(2) 0.4001(17) 0.4802(11) 0.046(4) Uiso 1 1 d . . . C1 C 0.22206(15) 0.26002(12) 0.42605(8) 0.0305(2) Uani 1 1 d . . . C2 C 0.27665(16) 0.18725(13) 0.34394(8) 0.0337(2) Uani 1 1 d . . . H2 H 0.2152 0.1213 0.3213 0.040 Uiso 1 1 calc R . . C3 C 0.43753(15) 0.22683(13) 0.29958(8) 0.0315(2) Uani 1 1 d . A . C4 C 0.47884(15) 0.32424(13) 0.35696(8) 0.0312(2) Uani 1 1 d . . . C5 C 0.62158(16) 0.40870(14) 0.34473(8) 0.0349(3) Uani 1 1 d . A . C6A C 0.8592(3) 0.4856(3) 0.23460(18) 0.0393(6) Uani 0.608(4) 1 d P A -1 H6A H 0.8117 0.5786 0.2634 0.047 Uiso 0.608(4) 1 calc PR A -1 H6B H 0.9757 0.4447 0.2581 0.047 Uiso 0.608(4) 1 calc PR A -1 C7A C 0.8826(4) 0.5128(3) 0.12727(18) 0.0480(7) Uani 0.608(4) 1 d P A -1 H7A H 0.7744 0.5736 0.1055 0.072 Uiso 0.608(4) 1 calc PR A -1 H7B H 0.9049 0.4196 0.0988 0.072 Uiso 0.608(4) 1 calc PR A -1 H7C H 0.9839 0.5632 0.1072 0.072 Uiso 0.608(4) 1 calc PR A -1 C6B C 0.8980(5) 0.4227(5) 0.2456(3) 0.0392(10) Uani 0.392(4) 1 d P A -2 H6B1 H 0.9903 0.3469 0.2164 0.047 Uiso 0.392(4) 1 calc PR A -2 H6B2 H 0.9376 0.4506 0.3038 0.047 Uiso 0.392(4) 1 calc PR A -2 C7B C 0.8495(7) 0.5503(7) 0.1760(5) 0.0749(17) Uani 0.392(4) 1 d P A -2 H7B1 H 0.7555 0.6213 0.2072 0.112 Uiso 0.392(4) 1 calc PR A -2 H7B2 H 0.8065 0.5187 0.1208 0.112 Uiso 0.392(4) 1 calc PR A -2 H7B3 H 0.9543 0.5957 0.1539 0.112 Uiso 0.392(4) 1 calc PR A -2 C11 C 0.05865(15) 0.25885(12) 0.49275(8) 0.0305(2) Uani 1 1 d . . . C12 C 0.02199(16) 0.33788(14) 0.57296(9) 0.0360(3) Uani 1 1 d . . . H12 H 0.1053 0.3939 0.5862 0.043 Uiso 1 1 calc R . . C13 C -0.13470(17) 0.33574(15) 0.63375(9) 0.0410(3) Uani 1 1 d . . . H13 H -0.1577 0.3902 0.6883 0.049 Uiso 1 1 calc R . . C14 C -0.25776(17) 0.25521(14) 0.61577(9) 0.0401(3) Uani 1 1 d . . . H14 H -0.3646 0.2536 0.6579 0.048 Uiso 1 1 calc R . . C15 C -0.22417(17) 0.17703(15) 0.53602(10) 0.0422(3) Uani 1 1 d . . . H15 H -0.3086 0.1220 0.5229 0.051 Uiso 1 1 calc R . . C16 C -0.06769(17) 0.17868(14) 0.47505(9) 0.0391(3) Uani 1 1 d . . . H16 H -0.0458 0.1245 0.4204 0.047 Uiso 1 1 calc R . . C31 C 0.53553(15) 0.17406(13) 0.20852(8) 0.0311(2) Uani 1 1 d . . . C32 C 0.64830(16) 0.03813(13) 0.20879(8) 0.0339(2) Uani 1 1 d . A . C33 C 0.73123(16) -0.01336(14) 0.12235(9) 0.0367(3) Uani 1 1 d . . . H33 H 0.8060 -0.1065 0.1234 0.044 Uiso 1 1 calc R A . C34 C 0.70749(16) 0.06840(14) 0.03377(9) 0.0359(3) Uani 1 1 d . A . C35 C 0.59547(16) 0.20456(14) 0.03500(8) 0.0358(3) Uani 1 1 d . . . H35 H 0.5768 0.2622 -0.0241 0.043 Uiso 1 1 calc R A . C36 C 0.51065(15) 0.25748(13) 0.12084(8) 0.0332(2) Uani 1 1 d . A . N34 N 0.79708(16) 0.01838(14) -0.05163(8) 0.0466(3) Uani 1 1 d . . . C37 C 0.6848(2) -0.05266(15) 0.30201(10) 0.0457(3) Uani 1 1 d . . . H37A H 0.7574 -0.1472 0.2881 0.069 Uiso 0.605(18) 1 calc PR A . H37B H 0.5718 -0.0680 0.3392 0.069 Uiso 0.605(18) 1 calc PR . . H37C H 0.7489 -0.0018 0.3392 0.069 Uiso 0.605(18) 1 calc PR . . H37D H 0.6280 0.0026 0.3563 0.069 Uiso 0.395(18) 1 calc PR . . H37E H 0.8136 -0.0767 0.3052 0.069 Uiso 0.395(18) 1 calc PR . . H37F H 0.6365 -0.1429 0.3052 0.069 Uiso 0.395(18) 1 calc PR . . C38 C 0.8747(2) -0.13355(16) -0.05443(11) 0.0509(4) Uani 1 1 d . A . H38A H 0.7814 -0.1931 -0.0369 0.076 Uiso 1 1 calc R . . H38B H 0.9638 -0.1602 -0.0088 0.076 Uiso 1 1 calc R . . H38C H 0.9318 -0.1508 -0.1195 0.076 Uiso 1 1 calc R . . C39 C 0.7585(2) 0.09976(19) -0.14206(10) 0.0536(4) Uani 1 1 d . A . H39A H 0.8387 0.0547 -0.1946 0.080 Uiso 1 1 calc R . . H39B H 0.7756 0.2006 -0.1412 0.080 Uiso 1 1 calc R . . H39C H 0.6349 0.0993 -0.1518 0.080 Uiso 1 1 calc R . . C40 C 0.39256(18) 0.40532(15) 0.11831(9) 0.0415(3) Uani 1 1 d . . . H40A H 0.2790 0.3982 0.1576 0.062 Uiso 1 1 calc R A . H40B H 0.3707 0.4394 0.0518 0.062 Uiso 1 1 calc R . . H40C H 0.4511 0.4745 0.1439 0.062 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 0.0372(4) 0.0474(5) 0.0356(4) -0.0135(4) 0.0021(3) -0.0166(4) O2 0.0513(5) 0.1164(9) 0.0424(5) -0.0414(5) 0.0200(4) -0.0513(6) N1 0.0301(5) 0.0353(5) 0.0269(4) -0.0073(4) -0.0003(4) -0.0083(4) C1 0.0315(5) 0.0321(5) 0.0285(5) -0.0016(4) -0.0030(4) -0.0084(4) C2 0.0364(6) 0.0369(6) 0.0302(5) -0.0060(4) -0.0007(4) -0.0129(5) C3 0.0335(5) 0.0352(5) 0.0271(5) -0.0054(4) -0.0024(4) -0.0087(4) C4 0.0298(5) 0.0384(6) 0.0264(5) -0.0072(4) 0.0001(4) -0.0079(4) C5 0.0319(5) 0.0473(6) 0.0276(5) -0.0087(5) 0.0006(4) -0.0121(5) C6A 0.0352(12) 0.0541(16) 0.0323(12) -0.0065(11) 0.0062(9) -0.0226(11) C7A 0.0503(14) 0.0629(15) 0.0299(12) -0.0004(10) 0.0032(10) -0.0153(11) C6B 0.0359(19) 0.042(2) 0.042(2) -0.0139(17) 0.0056(15) -0.0153(16) C7B 0.060(3) 0.090(4) 0.073(4) 0.022(3) -0.002(3) -0.033(3) C11 0.0315(5) 0.0304(5) 0.0285(5) 0.0009(4) -0.0014(4) -0.0060(4) C12 0.0340(6) 0.0418(6) 0.0336(6) -0.0062(5) 0.0007(5) -0.0118(5) C13 0.0384(6) 0.0490(7) 0.0348(6) -0.0080(5) 0.0048(5) -0.0099(5) C14 0.0317(6) 0.0456(7) 0.0397(7) 0.0033(5) 0.0041(5) -0.0082(5) C15 0.0370(6) 0.0473(7) 0.0446(7) -0.0006(5) -0.0016(5) -0.0177(5) C16 0.0401(6) 0.0426(6) 0.0365(6) -0.0064(5) 0.0007(5) -0.0145(5) C31 0.0305(5) 0.0390(6) 0.0267(5) -0.0087(4) -0.0003(4) -0.0122(4) C32 0.0331(5) 0.0387(6) 0.0319(6) -0.0064(5) -0.0003(4) -0.0120(5) C33 0.0337(6) 0.0384(6) 0.0388(6) -0.0108(5) 0.0012(5) -0.0078(5) C34 0.0334(6) 0.0478(6) 0.0305(6) -0.0139(5) 0.0022(4) -0.0154(5) C35 0.0366(6) 0.0463(6) 0.0273(5) -0.0054(5) -0.0029(4) -0.0138(5) C36 0.0316(5) 0.0403(6) 0.0306(5) -0.0071(5) -0.0027(4) -0.0116(5) N34 0.0502(6) 0.0578(7) 0.0332(5) -0.0186(5) 0.0060(5) -0.0117(5) C37 0.0509(8) 0.0456(7) 0.0378(7) -0.0021(6) -0.0018(6) -0.0047(6) C38 0.0489(8) 0.0574(8) 0.0508(8) -0.0279(6) 0.0097(6) -0.0174(6) C39 0.0565(8) 0.0775(10) 0.0305(6) -0.0176(6) 0.0040(6) -0.0195(7) C40 0.0435(7) 0.0449(7) 0.0350(6) -0.0044(5) -0.0023(5) -0.0054(5) _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 C5 1.2077(15) . ? O2 C5 1.3393(14) . ? O2 C6B 1.401(4) . ? O2 C6A 1.517(3) . ? N1 C1 1.3631(15) . ? N1 C4 1.3758(14) . ? N1 H1 0.904(16) . ? C1 C2 1.3873(16) . ? C1 C11 1.4678(16) . ? C2 C3 1.4057(16) . ? C2 H2 0.9500 . ? C3 C4 1.3913(16) . ? C3 C31 1.4860(15) . ? C4 C5 1.4525(17) . ? C6A C7A 1.496(3) . ? C6A H6A 0.9900 . ? C6A H6B 0.9900 . ? C7A H7A 0.9800 . ? C7A H7B 0.9800 . ? C7A H7C 0.9800 . ? C6B C7B 1.479(7) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7B H7B1 0.9800 . ? C7B H7B2 0.9800 . ? C7B H7B3 0.9800 . ? C11 C12 1.3908(17) . ? C11 C16 1.3984(17) . ? C12 C13 1.3855(17) . ? C12 H12 0.9500 . ? C13 C14 1.3814(19) . ? C13 H13 0.9500 . ? C14 C15 1.3810(19) . ? C14 H14 0.9500 . ? C15 C16 1.3849(18) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C31 C36 1.3981(16) . ? C31 C32 1.3998(17) . ? C32 C33 1.3915(16) . ? C32 C37 1.5082(18) . ? C33 C34 1.4009(18) . ? C33 H33 0.9500 . ? C34 N34 1.3894(15) . ? C34 C35 1.3995(18) . ? C35 C36 1.3933(16) . ? C35 H35 0.9500 . ? C36 C40 1.5066(17) . ? N34 C38 1.4396(19) . ? N34 C39 1.4427(19) . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C37 H37D 0.9800 . ? C37 H37E 0.9800 . ? C37 H37F 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 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 C5 O2 C6B 122.45(19) . . ? C5 O2 C6A 114.13(14) . . ? C1 N1 C4 109.76(9) . . ? C1 N1 H1 126.5(10) . . ? C4 N1 H1 123.8(10) . . ? N1 C1 C2 106.96(10) . . ? N1 C1 C11 124.27(10) . . ? C2 C1 C11 128.73(11) . . ? C1 C2 C3 109.00(10) . . ? C1 C2 H2 125.5 . . ? C3 C2 H2 125.5 . . ? C4 C3 C2 105.97(10) . . ? C4 C3 C31 129.06(11) . . ? C2 C3 C31 124.96(10) . . ? N1 C4 C3 108.29(10) . . ? N1 C4 C5 120.22(10) . . ? C3 C4 C5 131.37(11) . . ? O1 C5 O2 123.71(11) . . ? O1 C5 C4 125.42(11) . . ? O2 C5 C4 110.85(10) . . ? C7A C6A O2 109.5(2) . . ? C7A C6A H6A 109.8 . . ? O2 C6A H6A 109.8 . . ? C7A C6A H6B 109.8 . . ? O2 C6A H6B 109.8 . . ? H6A C6A H6B 108.2 . . ? O2 C6B C7B 98.2(3) . . ? O2 C6B H6B1 112.1 . . ? C7B C6B H6B1 112.1 . . ? O2 C6B H6B2 112.1 . . ? C7B C6B H6B2 112.1 . . ? H6B1 C6B H6B2 109.8 . . ? C6B C7B H7B1 109.5 . . ? C6B C7B H7B2 109.5 . . ? H7B1 C7B H7B2 109.5 . . ? C6B C7B H7B3 109.5 . . ? H7B1 C7B H7B3 109.5 . . ? H7B2 C7B H7B3 109.5 . . ? C12 C11 C16 118.08(11) . . ? C12 C11 C1 122.22(11) . . ? C16 C11 C1 119.69(11) . . ? C13 C12 C11 120.68(12) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 120.62(12) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 119.47(12) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 120.16(12) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 121.00(12) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? C36 C31 C32 119.13(10) . . ? C36 C31 C3 120.19(10) . . ? C32 C31 C3 120.63(10) . . ? C33 C32 C31 119.93(11) . . ? C33 C32 C37 119.19(11) . . ? C31 C32 C37 120.87(11) . . ? C32 C33 C34 121.77(11) . . ? C32 C33 H33 119.1 . . ? C34 C33 H33 119.1 . . ? N34 C34 C35 121.35(12) . . ? N34 C34 C33 121.14(12) . . ? C35 C34 C33 117.48(11) . . ? C36 C35 C34 121.52(11) . . ? C36 C35 H35 119.2 . . ? C34 C35 H35 119.2 . . ? C35 C36 C31 120.17(11) . . ? C35 C36 C40 119.44(11) . . ? C31 C36 C40 120.39(10) . . ? C34 N34 C38 119.70(12) . . ? C34 N34 C39 119.53(12) . . ? C38 N34 C39 116.92(11) . . ? C32 C37 H37A 109.5 . . ? C32 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C32 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C32 C37 H37D 109.5 . . ? H37A C37 H37D 141.1 . . ? H37B C37 H37D 56.3 . . ? H37C C37 H37D 56.3 . . ? C32 C37 H37E 109.5 . . ? H37A C37 H37E 56.3 . . ? H37B C37 H37E 141.1 . . ? H37C C37 H37E 56.3 . . ? H37D C37 H37E 109.5 . . ? C32 C37 H37F 109.5 . . ? H37A C37 H37F 56.3 . . ? H37B C37 H37F 56.3 . . ? H37C C37 H37F 141.1 . . ? H37D C37 H37F 109.5 . . ? H37E C37 H37F 109.5 . . ? N34 C38 H38A 109.5 . . ? N34 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? N34 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N34 C39 H39A 109.5 . . ? N34 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? N34 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C36 C40 H40A 109.5 . . ? C36 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C36 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? 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 C4 N1 C1 C2 1.25(13) . . . . ? C4 N1 C1 C11 -176.58(10) . . . . ? N1 C1 C2 C3 -0.94(13) . . . . ? C11 C1 C2 C3 176.77(11) . . . . ? C1 C2 C3 C4 0.28(13) . . . . ? C1 C2 C3 C31 -178.52(11) . . . . ? C1 N1 C4 C3 -1.10(13) . . . . ? C1 N1 C4 C5 175.37(10) . . . . ? C2 C3 C4 N1 0.48(13) . . . . ? C31 C3 C4 N1 179.22(11) . . . . ? C2 C3 C4 C5 -175.45(12) . . . . ? C31 C3 C4 C5 3.3(2) . . . . ? C6B O2 C5 O1 14.5(3) . . . . ? C6A O2 C5 O1 -11.3(2) . . . . ? C6B O2 C5 C4 -167.0(2) . . . . ? C6A O2 C5 C4 167.17(15) . . . . ? N1 C4 C5 O1 0.34(19) . . . . ? C3 C4 C5 O1 175.87(13) . . . . ? N1 C4 C5 O2 -178.08(11) . . . . ? C3 C4 C5 O2 -2.55(19) . . . . ? C5 O2 C6A C7A -142.2(2) . . . . ? C6B O2 C6A C7A 101.8(6) . . . . ? C5 O2 C6B C7B -101.8(4) . . . . ? C6A O2 C6B C7B -25.3(5) . . . . ? N1 C1 C11 C12 -2.80(18) . . . . ? C2 C1 C11 C12 179.85(12) . . . . ? N1 C1 C11 C16 175.80(11) . . . . ? C2 C1 C11 C16 -1.55(18) . . . . ? C16 C11 C12 C13 0.56(18) . . . . ? C1 C11 C12 C13 179.17(11) . . . . ? C11 C12 C13 C14 -0.1(2) . . . . ? C12 C13 C14 C15 -0.4(2) . . . . ? C13 C14 C15 C16 0.5(2) . . . . ? C14 C15 C16 C11 0.0(2) . . . . ? C12 C11 C16 C15 -0.51(18) . . . . ? C1 C11 C16 C15 -179.16(11) . . . . ? C4 C3 C31 C36 -83.14(16) . . . . ? C2 C3 C31 C36 95.38(15) . . . . ? C4 C3 C31 C32 99.36(15) . . . . ? C2 C3 C31 C32 -82.12(15) . . . . ? C36 C31 C32 C33 -1.18(17) . . . . ? C3 C31 C32 C33 176.35(11) . . . . ? C36 C31 C32 C37 177.48(11) . . . . ? C3 C31 C32 C37 -4.99(17) . . . . ? C31 C32 C33 C34 0.99(18) . . . . ? C37 C32 C33 C34 -177.69(12) . . . . ? C32 C33 C34 N34 177.22(11) . . . . ? C32 C33 C34 C35 -0.44(18) . . . . ? N34 C34 C35 C36 -177.55(11) . . . . ? C33 C34 C35 C36 0.10(18) . . . . ? C34 C35 C36 C31 -0.32(18) . . . . ? C34 C35 C36 C40 179.50(11) . . . . ? C32 C31 C36 C35 0.85(17) . . . . ? C3 C31 C36 C35 -176.69(11) . . . . ? C32 C31 C36 C40 -178.97(11) . . . . ? C3 C31 C36 C40 3.49(17) . . . . ? C35 C34 N34 C38 -164.68(12) . . . . ? C33 C34 N34 C38 17.75(19) . . . . ? C35 C34 N34 C39 -7.43(19) . . . . ? C33 C34 N34 C39 175.01(12) . . . . ? 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 N1 H1 O1 0.904(16) 2.094(16) 2.9889(13) 170.3(14) 2_666