data_2203333 loop_ _publ_author_name Vasu 'K. A. Nirmala' 'Deepak Chopra' 'S. Mohan' J.Saravanan _publ_section_title ; 2-Amino-N-(2-chlorophenyl)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxamide ; _journal_issue 3 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o437 _journal_page_last o438 _journal_volume 60 _journal_year 2004 _chemical_formula_moiety 'C14 H13 Cl N2 O S' _chemical_formula_structural ? _chemical_formula_sum 'C14 H13 Cl N2 O S' _chemical_formula_weight 292.78 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ; ? ; _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 111.912(4) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 9.939(3) _cell_length_b 29.449(8) _cell_length_c 9.747(3) _cell_measurement_reflns_used 600 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.5 _cell_measurement_theta_min 2.0 _cell_volume 2646.8(14) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.962 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 19431 _diffrn_reflns_reduction_process ; ? ; _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 1.38 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _exptl_absorpt_coefficient_mu 0.439 _exptl_absorpt_correction_T_max 0.8616 _exptl_absorpt_correction_T_min 0.7788 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1997)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description block _exptl_crystal_F_000 1216 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_size_rad ? _refine_diff_density_max 0.341 _refine_diff_density_min -0.232 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 447 _refine_ls_number_reflns 5215 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.145 _refine_ls_R_factor_all 0.0792 _refine_ls_R_factor_gt 0.0568 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0488P)^2^+1.7113P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1212 _refine_ls_wR_factor_ref 0.1303 _reflns_number_gt 4005 _reflns_number_total 5215 _reflns_threshold_expression I>2\s(I) loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S1 0.66111(9) 0.18736(3) 0.86308(10) 0.0523(2) Uani d . 1 . . S S2 1.16488(9) 0.05914(3) 0.90025(10) 0.0499(2) Uani d . 1 . . S Cl1 1.10786(10) 0.33831(3) 0.65822(11) 0.0598(3) Uani d . 1 . . Cl Cl2 1.55132(11) -0.10306(3) 0.65134(13) 0.0731(3) Uani d . 1 . . Cl O1 1.0466(2) 0.16585(6) 0.7236(3) 0.0568(6) Uani d . 1 . . O O2 1.5621(2) 0.06872(7) 0.7754(3) 0.0543(6) Uani d . 1 . . O N1 1.0436(3) 0.24232(8) 0.6889(3) 0.0442(6) Uani d . 1 . . N N2 1.5368(3) -0.00714(9) 0.7300(3) 0.0438(6) Uani d . 1 . . N N3 1.3497(4) 0.11400(9) 0.8383(4) 0.0566(8) Uani d . 1 . . N N4 0.8251(4) 0.12740(9) 0.7893(4) 0.0585(8) Uani d . 1 . . N C1 0.7182(5) 0.32347(12) 0.8415(6) 0.0677(11) Uani d . 1 . . C C2 0.6359(4) 0.28646(11) 0.8903(4) 0.0487(8) Uani d . 1 . . C C3 0.6990(3) 0.24427(10) 0.8533(3) 0.0445(7) Uani d . 1 . . C C4 0.8112(3) 0.25097(9) 0.8099(3) 0.0377(6) Uani d . 1 . . C C5 0.8415(4) 0.30091(9) 0.8068(4) 0.0446(7) Uani d . 1 . . C C6 0.8749(3) 0.20948(8) 0.7819(3) 0.0362(6) Uani d . 1 . . C C7 0.8014(3) 0.17194(9) 0.8061(3) 0.0413(7) Uani d . 1 . . C C8 0.9940(3) 0.20348(9) 0.7312(3) 0.0382(6) Uani d . 1 . . C C9 1.1534(3) 0.24807(9) 0.6335(3) 0.0381(6) Uani d . 1 . . C C10 1.2228(3) 0.21268(11) 0.5914(4) 0.0466(7) Uani d . 1 . . C C11 1.3300(4) 0.22133(13) 0.5378(4) 0.0563(9) Uani d . 1 . . C C12 1.3703(4) 0.26535(13) 0.5228(4) 0.0594(9) Uani d . 1 . . C C13 1.3025(4) 0.30110(12) 0.5615(4) 0.0530(8) Uani d . 1 . . C C14 1.1953(3) 0.29241(10) 0.6154(3) 0.0421(7) Uani d . 1 . . C C15 1.1742(4) -0.07771(11) 0.8552(5) 0.0530(9) Uani d . 1 . . C C16 1.3107(3) -0.05949(9) 0.8333(4) 0.0405(7) Uani d . 1 . . C C17 1.2976(3) -0.00883(8) 0.8446(3) 0.0334(6) Uani d . 1 . . C C18 1.1074(4) -0.03857(10) 0.9140(4) 0.0479(8) Uani d . 1 . . C C19 1.1858(3) 0.00115(9) 0.8843(3) 0.0394(6) Uani d . 1 . . C C20 1.3760(3) 0.03065(8) 0.8252(3) 0.0338(6) Uani d . 1 . . C C21 1.3120(3) 0.07004(9) 0.8493(3) 0.0403(7) Uani d . 1 . . C C22 1.4981(3) 0.03288(9) 0.7766(3) 0.0374(6) Uani d . 1 . . C C23 1.6385(3) -0.01548(10) 0.6646(3) 0.0404(7) Uani d . 1 . . C C24 1.7204(4) 0.01843(13) 0.6320(4) 0.0554(9) Uani d . 1 . . C C25 1.8171(4) 0.00773(15) 0.5665(4) 0.0629(10) Uani d . 1 . . C C26 1.8350(4) -0.03602(15) 0.5294(4) 0.0636(10) Uani d . 1 . . C C27 1.7542(4) -0.07019(13) 0.5583(4) 0.0580(9) Uani d . 1 . . C C28 1.6569(3) -0.05991(10) 0.6242(3) 0.0462(7) Uani d . 1 . . C H1A 0.761(4) 0.3470(15) 0.916(4) 0.088(14) Uiso d . 1 . . H H1B 0.653(4) 0.3373(14) 0.755(5) 0.086(14) Uiso d . 1 . . H H1N 1.001(4) 0.2627(11) 0.695(4) 0.050(10) Uiso d . 1 . . H H2A 0.661(3) 0.2878(10) 0.995(4) 0.050(9) Uiso d . 1 . . H H2B 0.534(4) 0.2879(10) 0.835(3) 0.047(9) Uiso d . 1 . . H H2N 1.490(4) -0.0262(11) 0.733(4) 0.055(11) Uiso d . 1 . . H H5A 0.939(4) 0.3093(11) 0.881(4) 0.061(10) Uiso d . 1 . . H H5B 0.836(3) 0.3111(10) 0.710(3) 0.047(8) Uiso d . 1 . . H H10 1.195(3) 0.1826(11) 0.598(3) 0.048(8) Uiso d . 1 . . H H11 1.376(4) 0.1983(13) 0.507(4) 0.080(12) Uiso d . 1 . . H H12 1.437(3) 0.2688(10) 0.483(3) 0.046(8) Uiso d . 1 . . H H13 1.327(4) 0.3339(12) 0.554(4) 0.069(10) Uiso d . 1 . . H H14N 0.897(5) 0.1210(13) 0.764(4) 0.081(14) Uiso d . 1 . . H H15A 1.195(4) -0.1020(13) 0.913(4) 0.069(11) Uiso d . 1 . . H H15B 1.109(4) -0.0859(12) 0.757(4) 0.069(11) Uiso d . 1 . . H H16A 1.402(4) -0.0706(10) 0.909(4) 0.053(9) Uiso d . 1 . . H H16B 1.311(3) -0.0682(9) 0.744(3) 0.039(8) Uiso d . 1 . . H H18A 1.006(4) -0.0362(11) 0.860(4) 0.057(10) Uiso d . 1 . . H H18B 1.128(3) -0.0413(10) 1.021(4) 0.052(9) Uiso d . 1 . . H H24 1.704(4) 0.0471(12) 0.655(4) 0.059(10) Uiso d . 1 . . H H24N 0.767(4) 0.1070(13) 0.797(4) 0.071(12) Uiso d . 1 . . H H25 1.870(4) 0.0313(13) 0.548(4) 0.080(12) Uiso d . 1 . . H H26 1.895(4) -0.0443(12) 0.480(4) 0.069(11) Uiso d . 1 . . H H27 1.763(4) -0.1022(12) 0.532(4) 0.067(11) Uiso d . 1 . . H H31N 1.416(4) 0.1184(11) 0.799(4) 0.055(10) Uiso d . 1 . . H H32N 1.283(4) 0.1327(12) 0.812(4) 0.065(11) Uiso d . 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0458(4) 0.0445(4) 0.0761(6) -0.0037(3) 0.0335(4) 0.0103(4) S2 0.0524(5) 0.0377(4) 0.0725(6) 0.0068(3) 0.0382(4) -0.0001(4) Cl1 0.0659(5) 0.0345(4) 0.0922(7) -0.0015(3) 0.0448(5) 0.0045(4) Cl2 0.0805(6) 0.0379(4) 0.1292(9) 0.0020(4) 0.0718(6) -0.0029(5) O1 0.0633(14) 0.0301(11) 0.0933(18) 0.0061(10) 0.0478(13) 0.0072(11) O2 0.0541(13) 0.0351(11) 0.0848(17) -0.0101(9) 0.0386(12) -0.0044(10) N1 0.0457(15) 0.0294(13) 0.0680(18) 0.0048(11) 0.0333(14) 0.0071(12) N2 0.0440(15) 0.0352(13) 0.0639(18) -0.0082(11) 0.0338(13) -0.0058(12) N3 0.0633(19) 0.0283(13) 0.090(2) 0.0016(13) 0.0430(18) -0.0003(13) N4 0.0614(19) 0.0277(13) 0.097(2) -0.0056(13) 0.0418(18) 0.0041(14) C1 0.066(2) 0.0434(19) 0.112(4) 0.0076(18) 0.055(3) 0.001(2) C2 0.0431(19) 0.0502(18) 0.057(2) 0.0061(14) 0.0233(17) 0.0029(15) C3 0.0397(16) 0.0401(16) 0.0578(19) 0.0009(12) 0.0226(15) 0.0038(14) C4 0.0368(15) 0.0334(14) 0.0427(16) 0.0004(11) 0.0146(13) 0.0035(12) C5 0.0476(19) 0.0304(14) 0.061(2) 0.0023(13) 0.0262(17) 0.0043(14) C6 0.0351(15) 0.0297(13) 0.0448(16) 0.0000(11) 0.0160(12) 0.0054(11) C7 0.0388(15) 0.0342(14) 0.0510(18) -0.0038(12) 0.0168(14) 0.0057(12) C8 0.0399(15) 0.0285(13) 0.0477(17) -0.0001(11) 0.0178(13) 0.0024(12) C9 0.0360(15) 0.0409(15) 0.0393(16) 0.0009(12) 0.0161(13) 0.0047(12) C10 0.0493(18) 0.0436(17) 0.0532(19) 0.0055(14) 0.0262(15) 0.0029(14) C11 0.057(2) 0.063(2) 0.058(2) 0.0085(17) 0.0318(18) -0.0025(17) C12 0.053(2) 0.075(2) 0.064(2) -0.0036(18) 0.0383(19) 0.0020(18) C13 0.0523(19) 0.059(2) 0.054(2) -0.0093(16) 0.0270(16) 0.0063(16) C14 0.0422(16) 0.0406(15) 0.0461(17) 0.0000(12) 0.0195(14) 0.0041(13) C15 0.059(2) 0.0385(17) 0.072(3) -0.0067(15) 0.037(2) 0.0022(17) C16 0.0451(18) 0.0311(14) 0.0506(19) -0.0021(12) 0.0240(15) -0.0018(13) C17 0.0376(15) 0.0275(13) 0.0373(15) 0.0002(11) 0.0164(12) 0.0012(11) C18 0.046(2) 0.0461(17) 0.060(2) -0.0026(14) 0.0295(17) 0.0080(15) C19 0.0409(16) 0.0348(14) 0.0476(17) 0.0026(12) 0.0223(14) 0.0014(12) C20 0.0334(14) 0.0313(13) 0.0380(15) -0.0017(11) 0.0149(12) -0.0015(11) C21 0.0420(16) 0.0318(14) 0.0483(17) -0.0007(11) 0.0183(13) -0.0011(12) C22 0.0380(15) 0.0323(14) 0.0436(16) -0.0034(11) 0.0173(13) -0.0007(12) C23 0.0352(15) 0.0468(16) 0.0440(17) -0.0042(12) 0.0204(13) -0.0035(13) C24 0.054(2) 0.058(2) 0.064(2) -0.0176(16) 0.0333(18) -0.0122(17) C25 0.051(2) 0.085(3) 0.064(2) -0.0185(19) 0.0348(18) -0.007(2) C26 0.047(2) 0.100(3) 0.056(2) 0.0013(19) 0.0320(18) -0.004(2) C27 0.051(2) 0.067(2) 0.066(2) 0.0086(17) 0.0334(18) -0.0049(18) C28 0.0396(16) 0.0477(17) 0.0563(19) 0.0023(13) 0.0237(14) 0.0005(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C19 S2 C21 . . 90.81(13) ? C3 S1 C7 . . 91.05(13) ? C8 N1 C9 . . 129.7(3) ? C8 N1 H1N . . 111(3) ? C9 N1 H1N . . 119(3) ? C21 C20 C17 . . 110.2(2) ? C21 C20 C22 . . 120.5(2) ? C17 C20 C22 . . 129.1(2) ? C22 N2 C23 . . 129.9(3) ? C22 N2 H2N . . 112(3) ? C23 N2 H2N . . 118(3) ? C21 N3 H31N . . 116(2) ? C21 N3 H32N . . 116(3) ? H31N N3 H32N . . 114(3) ? C19 C17 C20 . . 114.0(2) ? C19 C17 C16 . . 110.1(2) ? C20 C17 C16 . . 136.0(2) ? C4 C3 C2 . . 115.2(3) ? C4 C3 S1 . . 112.5(2) ? C2 C3 S1 . . 132.3(2) ? C14 C13 C12 . . 119.4(3) ? C14 C13 H13 . . 117(2) ? C12 C13 H13 . . 124(2) ? C10 C11 C12 . . 120.8(3) ? C10 C11 H11 . . 122(2) ? C12 C11 H11 . . 117(2) ? C4 C5 C1 . . 103.7(3) ? C4 C5 H5B . . 112.5(18) ? C1 C5 H5B . . 108.7(18) ? C4 C5 H5A . . 112.0(19) ? C1 C5 H5A . . 111.6(19) ? H5B C5 H5A . . 108(3) ? C7 N4 H14N . . 117(3) ? C7 N4 H24N . . 121(3) ? H14N N4 H24N . . 122(4) ? C17 C16 C15 . . 103.2(2) ? C17 C16 H16B . . 112.3(18) ? C15 C16 H16B . . 110.5(18) ? C17 C16 H16A . . 110.8(18) ? C15 C16 H16A . . 112.8(18) ? H16B C16 H16A . . 107(3) ? C7 C6 C4 . . 110.1(2) ? C7 C6 C8 . . 120.4(2) ? C4 C6 C8 . . 129.4(2) ? O1 C8 N1 . . 121.5(3) ? O1 C8 C6 . . 123.0(2) ? N1 C8 C6 . . 115.6(2) ? C11 C10 C9 . . 120.8(3) ? C11 C10 H10 . . 119.6(19) ? C9 C10 H10 . . 119.5(19) ? C10 C9 N1 . . 124.6(3) ? C10 C9 C14 . . 117.2(3) ? N1 C9 C14 . . 118.3(3) ? C24 C23 C28 . . 117.2(3) ? C24 C23 N2 . . 123.9(3) ? C28 C23 N2 . . 118.9(3) ? N3 C21 C20 . . 128.7(3) ? N3 C21 S2 . . 118.9(2) ? C20 C21 S2 . . 112.5(2) ? C19 C18 C15 . . 100.7(2) ? C19 C18 H18A . . 111.1(19) ? C15 C18 H18A . . 112(2) ? C19 C18 H18B . . 110.7(18) ? C15 C18 H18B . . 112.6(18) ? H18A C18 H18B . . 110(3) ? N4 C7 C6 . . 128.5(3) ? N4 C7 S1 . . 119.1(2) ? C6 C7 S1 . . 112.3(2) ? C13 C14 C9 . . 122.0(3) ? C13 C14 Cl1 . . 118.3(2) ? C9 C14 Cl1 . . 119.7(2) ? C3 C2 C1 . . 101.2(3) ? C3 C2 H2A . . 109.1(18) ? C1 C2 H2A . . 110.2(19) ? C3 C2 H2B . . 110.8(18) ? C1 C2 H2B . . 111.6(18) ? H2A C2 H2B . . 113(3) ? C13 C12 C11 . . 119.9(3) ? C13 C12 H12 . . 124(2) ? C11 C12 H12 . . 117(2) ? O2 C22 N2 . . 121.5(3) ? O2 C22 C20 . . 122.4(2) ? N2 C22 C20 . . 116.1(2) ? C3 C4 C6 . . 114.0(2) ? C3 C4 C5 . . 110.2(2) ? C6 C4 C5 . . 135.8(3) ? C5 C1 C2 . . 108.7(3) ? C5 C1 H1A . . 108(2) ? C2 C1 H1A . . 114(2) ? C5 C1 H1B . . 109(3) ? C2 C1 H1B . . 108(3) ? H1A C1 H1B . . 109(3) ? C25 C24 C23 . . 120.6(3) ? C25 C24 H24 . . 123(2) ? C23 C24 H24 . . 116(2) ? C27 C28 C23 . . 121.6(3) ? C27 C28 Cl2 . . 118.7(3) ? C23 C28 Cl2 . . 119.6(2) ? C18 C15 C16 . . 108.3(3) ? C18 C15 H15A . . 113(2) ? C16 C15 H15A . . 111(2) ? C18 C15 H15B . . 110(2) ? C16 C15 H15B . . 104(2) ? H15A C15 H15B . . 110(3) ? C25 C26 C27 . . 119.3(3) ? C25 C26 H26 . . 124(2) ? C27 C26 H26 . . 117(2) ? C28 C27 C26 . . 119.8(3) ? C28 C27 H27 . . 118(2) ? C26 C27 H27 . . 122(2) ? C17 C19 C18 . . 115.7(2) ? C17 C19 S2 . . 112.5(2) ? C18 C19 S2 . . 131.7(2) ? C26 C25 C24 . . 121.4(4) ? C26 C25 H25 . . 121(2) ? C24 C25 H25 . . 117(3) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S2 C19 . 1.734(3) ? S2 C21 . 1.741(3) ? Cl1 C14 . 1.740(3) ? S1 C3 . 1.728(3) ? S1 C7 . 1.743(3) ? Cl2 C28 . 1.730(3) ? O2 C22 . 1.235(3) ? O1 C8 . 1.239(3) ? N1 C8 . 1.369(3) ? N1 C9 . 1.396(4) ? N1 H1N . 0.75(3) ? C20 C21 . 1.384(4) ? C20 C17 . 1.451(3) ? C20 C22 . 1.459(4) ? N2 C22 . 1.369(4) ? N2 C23 . 1.403(4) ? N2 H2N . 0.74(3) ? N3 C21 . 1.363(4) ? N3 H31N . 0.88(4) ? N3 H32N . 0.83(4) ? C17 C19 . 1.338(4) ? C17 C16 . 1.505(4) ? C3 C4 . 1.347(4) ? C3 C2 . 1.495(4) ? C13 C14 . 1.376(4) ? C13 C12 . 1.377(5) ? C13 H13 . 1.01(4) ? C11 C10 . 1.374(4) ? C11 C12 . 1.381(5) ? C11 H11 . 0.93(4) ? C5 C4 . 1.504(4) ? C5 C1 . 1.538(4) ? C5 H5B . 0.97(3) ? C5 H5A . 1.00(3) ? N4 C7 . 1.353(4) ? N4 H14N . 0.86(4) ? N4 H24N . 0.85(4) ? C16 C15 . 1.547(4) ? C16 H16B . 0.91(3) ? C16 H16A . 0.98(3) ? C6 C7 . 1.393(4) ? C6 C4 . 1.448(4) ? C6 C8 . 1.454(4) ? C10 C9 . 1.394(4) ? C10 H10 . 0.94(3) ? C9 C14 . 1.402(4) ? C23 C24 . 1.397(4) ? C23 C28 . 1.398(4) ? C18 C19 . 1.493(4) ? C18 C15 . 1.543(5) ? C18 H18A . 0.95(3) ? C18 H18B . 0.99(3) ? C2 C1 . 1.541(5) ? C2 H2A . 0.95(3) ? C2 H2B . 0.95(3) ? C12 H12 . 0.89(3) ? C1 H1A . 0.98(4) ? C1 H1B . 0.95(4) ? C24 C25 . 1.374(5) ? C24 H24 . 0.90(3) ? C28 C27 . 1.379(4) ? C15 H15A . 0.89(4) ? C15 H15B . 0.97(4) ? C26 C25 . 1.367(5) ? C26 C27 . 1.380(5) ? C26 H26 . 0.93(4) ? C27 H27 . 0.99(4) ? C25 H25 . 0.93(4) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N4 H24N O2 1_455 0.86(4) 2.27(4) 3.094(5) 162(4) yes N3 H32N O1 1_555 0.83(4) 2.39(4) 3.186(5) 162(3) yes N4 H14N O1 1_555 0.86(5) 2.13(5) 2.755(5) 129(4) yes N3 H31N O2 1_555 0.88(4) 2.14(4) 2.752(5) 126(3) yes C10 H10 O1 1_555 0.94(3) 2.29(4) 2.883(5) 120(2) yes C24 H24 O2 1_555 0.90(4) 2.24(4) 2.875(5) 127(3) yes