# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Santiago Luis' _publ_contact_author_email LUISS@QIO.UJI.ES _publ_section_title ; A simple peptidomimetic that self-associates on the solid state to form a nanoporous architecture containing chiral ?-channels ; loop_ _publ_author_name 'Santiago Luis' 'Jorge Becerril' 'Michael Bolte' 'M Isabel Burguete' 'Jorge Escorihuela' 'Francisco Galindo' # Attachment '4a.cif' data_4a _database_code_depnum_ccdc_archive 'CCDC 279709' #TrackingRef '4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21.33 H29.33 N4 O2.33' _chemical_formula_weight 379.15 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 Hexagonal _symmetry_space_group_name_H-M P64 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+2/3' '-y, x-y, z+1/3' '-x, -y, z' '-x+y, -x, z+2/3' 'y, -x+y, z+1/3' _cell_length_a 16.994(2) _cell_length_b 16.994(2) _cell_length_c 6.2966(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1574.8(3) _cell_formula_units_Z 3 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 449 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 22. _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9420 _exptl_absorpt_correction_T_max 0.9704 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ; _diffrn_ambient_temperature 173(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 CCD three-circle diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 255 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1400 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14595 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 27.99 _reflns_number_total 2348 _reflns_number_gt 2221 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Siemens XTL-Plus)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0484P)^2^+0.1351P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.8(12) _refine_ls_number_reflns 2348 _refine_ls_number_parameters 130 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.46211(9) 0.24970(9) 0.2268(2) 0.0278(3) Uani 1 1 d . . . H1A H 0.4481 0.2012 0.1215 0.033 Uiso 1 1 calc R . . H1B H 0.4657 0.2259 0.3679 0.033 Uiso 1 1 calc R . . C2 C 0.55627(8) 0.33168(9) 0.17357(19) 0.0244(3) Uani 1 1 d . . . H2 H 0.5996 0.3090 0.1489 0.029 Uiso 1 1 calc R . . N21 N 0.59211(8) 0.39895(8) 0.34580(18) 0.0280(2) Uani 1 1 d . . . H21A H 0.6524(12) 0.4248(12) 0.357(3) 0.038(4) Uiso 1 1 d . . . H21B H 0.5634(12) 0.3693(11) 0.477(3) 0.041(4) Uiso 1 1 d . . . C3 C 0.54706(8) 0.37398(8) -0.0334(2) 0.0224(2) Uani 1 1 d . . . O31 O 0.52750(7) 0.33023(6) -0.20138(14) 0.0296(2) Uani 1 1 d . . . N4 N 0.56055(7) 0.45823(7) -0.01580(17) 0.0245(2) Uani 1 1 d . . . H4 H 0.5722(11) 0.4819(11) 0.111(3) 0.036(4) Uiso 1 1 d . . . C5 C 0.54788(9) 0.50634(9) -0.1920(2) 0.0287(3) Uani 1 1 d . . . H5A H 0.5583 0.4835 -0.3276 0.034 Uiso 1 1 calc R . . H5B H 0.5931 0.5719 -0.1815 0.034 Uiso 1 1 calc R . . C11 C 0.38391(8) 0.26893(8) 0.2299(2) 0.0255(3) Uani 1 1 d . . . C12 C 0.36753(10) 0.30835(11) 0.4053(3) 0.0367(3) Uani 1 1 d . . . H12 H 0.4061 0.3244 0.5260 0.044 Uiso 1 1 calc R . . C13 C 0.29483(11) 0.32441(13) 0.4048(3) 0.0485(4) Uani 1 1 d . . . H13 H 0.2847 0.3519 0.5251 0.058 Uiso 1 1 calc R . . C14 C 0.23748(10) 0.30118(11) 0.2330(3) 0.0451(4) Uani 1 1 d . . . H14 H 0.1878 0.3120 0.2349 0.054 Uiso 1 1 calc R . . C15 C 0.25295(11) 0.26187(13) 0.0575(3) 0.0471(4) Uani 1 1 d . . . H15 H 0.2139 0.2458 -0.0623 0.057 Uiso 1 1 calc R . . C16 C 0.32593(10) 0.24586(10) 0.0563(2) 0.0379(3) Uani 1 1 d . . . H16 H 0.3361 0.2188 -0.0649 0.046 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 C1 0.0337(7) 0.0269(6) 0.0274(6) 0.0037(5) 0.0015(5) 0.0186(5) C2 0.0296(6) 0.0319(6) 0.0196(6) 0.0011(5) 0.0009(5) 0.0213(5) N21 0.0287(6) 0.0359(6) 0.0199(5) 0.0000(5) -0.0016(4) 0.0165(5) C3 0.0207(5) 0.0297(6) 0.0203(6) 0.0020(5) 0.0033(4) 0.0153(5) O31 0.0397(5) 0.0363(5) 0.0195(4) -0.0014(4) 0.0009(4) 0.0240(4) N4 0.0292(5) 0.0295(5) 0.0197(5) 0.0015(4) 0.0014(4) 0.0183(4) C5 0.0418(8) 0.0314(6) 0.0212(6) 0.0058(5) 0.0071(5) 0.0245(6) C11 0.0267(6) 0.0210(5) 0.0273(6) 0.0066(5) 0.0025(5) 0.0109(5) C12 0.0331(7) 0.0481(8) 0.0333(7) -0.0096(6) -0.0043(6) 0.0236(6) C13 0.0412(8) 0.0603(10) 0.0532(10) -0.0133(8) -0.0012(8) 0.0324(8) C14 0.0344(8) 0.0546(9) 0.0554(10) 0.0109(8) 0.0026(7) 0.0292(7) C15 0.0353(8) 0.0643(10) 0.0399(8) 0.0074(8) -0.0070(7) 0.0235(7) C16 0.0384(7) 0.0447(8) 0.0293(7) -0.0036(6) -0.0035(6) 0.0197(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 C1 C11 1.5191(17) . ? C1 C2 1.5442(18) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N21 1.4688(16) . ? C2 C3 1.5337(17) . ? C2 H2 1.0000 . ? N21 H21A 0.893(17) . ? N21 H21B 0.96(2) . ? C3 O31 1.2389(16) . ? C3 N4 1.3365(16) . ? N4 C5 1.4568(17) . ? N4 H4 0.871(18) . ? C5 C5 1.531(3) 4_665 ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C11 C12 1.390(2) . ? C11 C16 1.390(2) . ? C12 C13 1.392(2) . ? C12 H12 0.9500 . ? C13 C14 1.375(3) . ? C13 H13 0.9500 . ? C14 C15 1.383(3) . ? C14 H14 0.9500 . ? C15 C16 1.396(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 C11 C1 C2 115.59(10) . . ? C11 C1 H1A 108.4 . . ? C2 C1 H1A 108.4 . . ? C11 C1 H1B 108.4 . . ? C2 C1 H1B 108.4 . . ? H1A C1 H1B 107.4 . . ? N21 C2 C3 111.25(10) . . ? N21 C2 C1 112.41(11) . . ? C3 C2 C1 107.75(10) . . ? N21 C2 H2 108.4 . . ? C3 C2 H2 108.4 . . ? C1 C2 H2 108.4 . . ? C2 N21 H21A 111.7(12) . . ? C2 N21 H21B 108.8(10) . . ? H21A N21 H21B 110.2(16) . . ? O31 C3 N4 124.38(11) . . ? O31 C3 C2 120.25(10) . . ? N4 C3 C2 115.37(11) . . ? C3 N4 C5 122.93(11) . . ? C3 N4 H4 116.7(11) . . ? C5 N4 H4 120.1(11) . . ? N4 C5 C5 111.46(10) . 4_665 ? N4 C5 H5A 109.3 . . ? C5 C5 H5A 109.3 4_665 . ? N4 C5 H5B 109.3 . . ? C5 C5 H5B 109.3 4_665 . ? H5A C5 H5B 108.0 . . ? C12 C11 C16 118.43(12) . . ? C12 C11 C1 121.42(13) . . ? C16 C11 C1 120.14(13) . . ? C11 C12 C13 120.26(15) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 121.10(16) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 119.26(14) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C14 C15 C16 120.02(14) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C11 C16 C15 120.93(14) . . ? C11 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? 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 C11 C1 C2 N21 70.78(14) . . . . ? C11 C1 C2 C3 -52.15(15) . . . . ? N21 C2 C3 O31 171.97(11) . . . . ? C1 C2 C3 O31 -64.39(14) . . . . ? N21 C2 C3 N4 -8.68(15) . . . . ? C1 C2 C3 N4 114.96(12) . . . . ? O31 C3 N4 C5 4.08(19) . . . . ? C2 C3 N4 C5 -175.24(11) . . . . ? C3 N4 C5 C5 93.62(14) . . . 4_665 ? C2 C1 C11 C12 -80.99(16) . . . . ? C2 C1 C11 C16 99.99(14) . . . . ? C16 C11 C12 C13 -0.3(2) . . . . ? C1 C11 C12 C13 -179.35(15) . . . . ? C11 C12 C13 C14 0.6(3) . . . . ? C12 C13 C14 C15 -0.5(3) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? C12 C11 C16 C15 0.1(2) . . . . ? C1 C11 C16 C15 179.10(13) . . . . ? C14 C15 C16 C11 0.0(2) . . . . ? 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 N4 H4 N21 0.871(18) 2.183(17) 2.6509(16) 113.2(13) . N21 H21A O31 0.893(17) 2.361(18) 3.2349(15) 165.9(15) 5_665 N21 H21B O31 0.96(2) 2.12(2) 3.0686(15) 166.5(15) 1_556 _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.136 _refine_diff_density_min -0.133 _refine_diff_density_rms 0.035 # Attachment '4ameso.cif' data_4a-meso _database_code_depnum_ccdc_archive 'CCDC 738995' #TrackingRef '4ameso.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H26 N4 O2' _chemical_formula_sum 'C20 H26 N4 O2' _chemical_formula_weight 354.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 8.327(2) _cell_length_b 12.216(3) _cell_length_c 9.643(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.648(6) _cell_angle_gamma 90.00 _cell_volume 969.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 500 _cell_measurement_theta_min 5 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_T_max . _exptl_absorpt_process_details . _exptl_special_details ; ; _diffrn_ambient_temperature 298(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 CCD three-circle diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7836 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 30.52 _reflns_number_total 2894 _reflns_number_gt 1963 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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^)+(0.0746P)^2^+0.1479P] 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 2894 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0824 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1569 _refine_ls_wR_factor_gt 0.1389 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.51384(16) 0.51161(8) 0.19598(11) 0.0590(3) Uani 1 1 d . . . N1 N 0.59602(18) 0.31910(10) 0.03290(13) 0.0451(3) Uani 1 1 d . . . H1A H 0.577(2) 0.3790(17) -0.021(2) 0.060(5) Uiso 1 1 d . . . H1B H 0.704(3) 0.3208(17) 0.077(3) 0.088(7) Uiso 1 1 d . . . N2 N 0.54411(14) 0.39106(9) 0.37422(11) 0.0366(3) Uani 1 1 d . . . H2 H 0.550(2) 0.3216(14) 0.4029(19) 0.053(4) Uiso 1 1 d . . . C1 C 0.3109(2) 0.32633(13) 0.05650(16) 0.0508(4) Uani 1 1 d . . . H1C H 0.3004 0.3932 0.0015 0.061 Uiso 1 1 calc R . . H1D H 0.2944 0.2653 -0.0084 0.061 Uiso 1 1 calc R . . C2 C 0.48329(18) 0.32006(10) 0.13649(13) 0.0397(3) Uani 1 1 d . . . H2A H 0.4955 0.2516 0.1900 0.048 Uiso 1 1 calc R . . C3 C 0.51519(17) 0.41655(10) 0.23855(13) 0.0376(3) Uani 1 1 d . . . C4 C 0.57728(17) 0.47468(11) 0.48203(13) 0.0396(3) Uani 1 1 d . . . H4A H 0.6440 0.5315 0.4497 0.047 Uiso 1 1 calc R . . H4B H 0.6379 0.4424 0.5658 0.047 Uiso 1 1 calc R . . C11 C 0.17900(19) 0.32431(12) 0.14758(16) 0.0504(4) Uani 1 1 d . . . C12 C 0.1123(3) 0.41795(19) 0.1904(4) 0.1072(10) Uani 1 1 d . . . H12 H 0.1469 0.4853 0.1610 0.129 Uiso 1 1 calc R . . C13 C -0.0067(4) 0.4147(3) 0.2771(4) 0.1328(13) Uani 1 1 d . . . H13 H -0.0500 0.4797 0.3053 0.159 Uiso 1 1 calc R . . C14 C -0.0601(3) 0.3183(2) 0.3209(3) 0.0896(8) Uani 1 1 d . . . H14 H -0.1409 0.3161 0.3777 0.107 Uiso 1 1 calc R . . C15 C 0.0050(3) 0.2267(2) 0.2812(3) 0.0881(7) Uani 1 1 d . . . H15 H -0.0301 0.1599 0.3117 0.106 Uiso 1 1 calc R . . C16 C 0.1243(3) 0.22830(16) 0.1954(2) 0.0747(6) Uani 1 1 d . . . H16 H 0.1679 0.1625 0.1698 0.090 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 0.1089(9) 0.0322(5) 0.0372(5) 0.0040(4) 0.0152(6) -0.0022(5) N1 0.0627(8) 0.0406(6) 0.0346(6) -0.0051(5) 0.0158(6) 0.0002(5) N2 0.0518(6) 0.0310(5) 0.0287(5) -0.0009(4) 0.0120(4) 0.0028(4) C1 0.0603(9) 0.0531(8) 0.0383(7) -0.0033(6) 0.0055(6) -0.0027(6) C2 0.0580(8) 0.0322(6) 0.0305(6) -0.0020(5) 0.0113(5) -0.0004(5) C3 0.0520(7) 0.0316(6) 0.0313(6) -0.0007(5) 0.0134(5) 0.0006(5) C4 0.0486(7) 0.0403(6) 0.0309(6) -0.0069(5) 0.0096(5) -0.0010(5) C11 0.0486(8) 0.0565(9) 0.0444(8) -0.0032(6) 0.0018(6) 0.0037(6) C12 0.0939(17) 0.0650(13) 0.177(3) 0.0047(15) 0.0678(19) 0.0182(11) C13 0.112(2) 0.099(2) 0.208(4) -0.010(2) 0.091(2) 0.0355(17) C14 0.0488(10) 0.137(2) 0.0860(15) 0.0055(14) 0.0202(10) 0.0170(12) C15 0.0836(15) 0.0963(17) 0.0905(16) 0.0182(13) 0.0329(12) -0.0004(12) C16 0.0884(14) 0.0630(11) 0.0802(13) -0.0002(10) 0.0367(11) -0.0014(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 C3 1.2312(15) . ? N1 C2 1.4701(17) . ? N1 H1A 0.90(2) . ? N1 H1B 0.94(3) . ? N2 C3 1.3311(16) . ? N2 C4 1.4540(16) . ? N2 H2 0.892(17) . ? C1 C11 1.506(2) . ? C1 C2 1.526(2) . ? C1 H1C 0.9700 . ? C1 H1D 0.9700 . ? C2 C3 1.5328(17) . ? C2 H2A 0.9800 . ? C4 C4 1.514(3) 3_666 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C11 C12 1.363(3) . ? C11 C16 1.363(2) . ? C12 C13 1.390(4) . ? C12 H12 0.9300 . ? C13 C14 1.349(4) . ? C13 H13 0.9300 . ? C14 C15 1.324(3) . ? C14 H14 0.9300 . ? C15 C16 1.385(3) . ? C15 H15 0.9300 . ? C16 H16 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 C2 N1 H1A 108.1(11) . . ? C2 N1 H1B 111.2(14) . . ? H1A N1 H1B 108.3(17) . . ? C3 N2 C4 121.69(11) . . ? C3 N2 H2 121.4(12) . . ? C4 N2 H2 116.8(12) . . ? C11 C1 C2 114.67(12) . . ? C11 C1 H1C 108.6 . . ? C2 C1 H1C 108.6 . . ? C11 C1 H1D 108.6 . . ? C2 C1 H1D 108.6 . . ? H1C C1 H1D 107.6 . . ? N1 C2 C1 107.77(12) . . ? N1 C2 C3 112.07(11) . . ? C1 C2 C3 110.18(11) . . ? N1 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? O1 C3 N2 122.65(12) . . ? O1 C3 C2 121.28(12) . . ? N2 C3 C2 116.07(10) . . ? N2 C4 C4 111.96(14) . 3_666 ? N2 C4 H4A 109.2 . . ? C4 C4 H4A 109.2 3_666 . ? N2 C4 H4B 109.2 . . ? C4 C4 H4B 109.2 3_666 . ? H4A C4 H4B 107.9 . . ? C12 C11 C16 116.59(18) . . ? C12 C11 C1 121.95(16) . . ? C16 C11 C1 121.42(15) . . ? C11 C12 C13 121.2(2) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C14 C13 C12 120.8(2) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C15 C14 C13 118.6(2) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? C14 C15 C16 121.5(2) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C11 C16 C15 121.33(19) . . ? C11 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? 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 C11 C1 C2 N1 178.08(12) . . . . ? C11 C1 C2 C3 -59.36(15) . . . . ? C4 N2 C3 O1 -0.4(2) . . . . ? C4 N2 C3 C2 179.59(11) . . . . ? N1 C2 C3 O1 56.31(18) . . . . ? C1 C2 C3 O1 -63.68(17) . . . . ? N1 C2 C3 N2 -123.65(13) . . . . ? C1 C2 C3 N2 116.36(13) . . . . ? C3 N2 C4 C4 82.62(18) . . . 3_666 ? C2 C1 C11 C12 94.7(2) . . . . ? C2 C1 C11 C16 -83.0(2) . . . . ? C16 C11 C12 C13 -0.7(4) . . . . ? C1 C11 C12 C13 -178.5(3) . . . . ? C11 C12 C13 C14 -0.4(6) . . . . ? C12 C13 C14 C15 1.0(5) . . . . ? C13 C14 C15 C16 -0.7(4) . . . . ? C12 C11 C16 C15 1.0(4) . . . . ? C1 C11 C16 C15 178.8(2) . . . . ? C14 C15 C16 C11 -0.3(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 N1 H1A O1 0.90(2) 2.20(2) 3.0623(18) 161.7(17) 3_665 N2 H2 N1 0.892(17) 2.127(18) 2.9867(17) 161.6(16) 4_566 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.193 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.046 #===END data_4a? _database_code_depnum_ccdc_archive 'CCDC 739838' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20.50 H27 Cl N4 O2' _chemical_formula_weight 396.91 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P64 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+2/3' '-y, x-y, z+1/3' '-x, -y, z' '-x+y, -x, z+2/3' 'y, -x+y, z+1/3' _cell_length_a 16.9390(10) _cell_length_b 16.9390(10) _cell_length_c 6.2865(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1562.12(18) _cell_formula_units_Z 3 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 501 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 19.7 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 633 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8590 _exptl_absorpt_correction_T_max 0.9257 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ; _diffrn_ambient_temperature 173(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 CCD three-circle diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 193 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1000 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15134 _diffrn_reflns_av_R_equivalents 0.0607 _diffrn_reflns_av_sigmaI/netI 0.0573 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 28.26 _reflns_number_total 2305 _reflns_number_gt 1728 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Siemens XTL-Plus)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(6) _refine_ls_number_reflns 2305 _refine_ls_number_parameters 144 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1338 _refine_ls_wR_factor_gt 0.1183 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.46177(15) 0.24916(15) 0.2266(4) 0.0273(5) Uani 1 1 d . . . H1A H 0.4477 0.2004 0.1214 0.033 Uiso 1 1 calc R . . H1B H 0.4655 0.2255 0.3681 0.033 Uiso 1 1 calc R . . C2 C 0.55628(14) 0.33175(15) 0.1726(4) 0.0240(5) Uani 1 1 d . . . H2 H 0.5999 0.3092 0.1481 0.029 Uiso 1 1 calc R . . N21 N 0.59165(16) 0.39879(15) 0.3445(4) 0.0279(5) Uani 1 1 d . . . H21A H 0.646(3) 0.424(2) 0.370(6) 0.060(10) Uiso 1 1 d . . . H21B H 0.5637(17) 0.3738(16) 0.468(5) 0.025(6) Uiso 1 1 d . . . C3 C 0.54687(14) 0.37376(14) -0.0340(4) 0.0226(5) Uani 1 1 d . . . O31 O 0.52739(11) 0.33009(11) -0.2025(3) 0.0290(4) Uani 1 1 d . . . N4 N 0.56078(12) 0.45848(12) -0.0168(3) 0.0232(4) Uani 1 1 d . . . H4 H 0.5767(17) 0.4845(16) 0.115(5) 0.030(7) Uiso 1 1 d . . . C5 C 0.54782(15) 0.50621(15) -0.1931(4) 0.0269(5) Uani 1 1 d . . . H5A H 0.5581 0.4830 -0.3287 0.032 Uiso 1 1 calc R . . H5B H 0.5933 0.5720 -0.1834 0.032 Uiso 1 1 calc R . . C11 C 0.38365(14) 0.26857(14) 0.2293(4) 0.0246(5) Uani 1 1 d . . . C12 C 0.36713(17) 0.30782(19) 0.4041(5) 0.0366(6) Uani 1 1 d . . . H12 H 0.4059 0.3238 0.5248 0.044 Uiso 1 1 calc R . . C13 C 0.29470(19) 0.3241(2) 0.4049(5) 0.0459(7) Uani 1 1 d . . . H13 H 0.2846 0.3516 0.5255 0.055 Uiso 1 1 calc R . . C14 C 0.23717(17) 0.30053(18) 0.2321(5) 0.0439(7) Uani 1 1 d . . . H14 H 0.1870 0.3109 0.2342 0.053 Uiso 1 1 calc R . . C15 C 0.25286(18) 0.2619(2) 0.0565(5) 0.0443(7) Uani 1 1 d . . . H15 H 0.2140 0.2463 -0.0639 0.053 Uiso 1 1 calc R . . C16 C 0.32559(18) 0.24576(17) 0.0554(4) 0.0373(6) Uani 1 1 d . . . H16 H 0.3358 0.2187 -0.0660 0.045 Uiso 1 1 calc R . . C1L C 0.0000 0.0000 -0.027(4) 0.30(3) Uani 0.50 2 d SPD . . H1L H 0.0210 0.0520 0.0643 0.360 Uiso 0.50 1 d PR . . Cl1 Cl 0.0923(5) 0.0110(6) -0.145(3) 0.350(6) Uani 0.50 1 d PD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0324(12) 0.0261(11) 0.0282(13) 0.0041(10) 0.0014(10) 0.0182(10) C2 0.0287(11) 0.0292(12) 0.0222(13) -0.0003(10) 0.0002(10) 0.0206(10) N21 0.0250(11) 0.0361(12) 0.0218(11) 0.0005(9) -0.0004(9) 0.0147(9) C3 0.0189(10) 0.0285(11) 0.0230(12) 0.0011(10) 0.0029(9) 0.0138(9) O31 0.0390(9) 0.0323(9) 0.0214(9) -0.0023(7) 0.0010(7) 0.0222(8) N4 0.0264(10) 0.0247(9) 0.0224(11) 0.0015(9) 0.0018(8) 0.0157(8) C5 0.0370(13) 0.0281(11) 0.0218(13) 0.0054(10) 0.0072(10) 0.0208(10) C11 0.0264(11) 0.0178(10) 0.0273(12) 0.0056(10) 0.0016(10) 0.0093(9) C12 0.0316(12) 0.0467(14) 0.0338(14) -0.0088(12) -0.0042(11) 0.0213(11) C13 0.0406(14) 0.0567(17) 0.0512(18) -0.0129(14) -0.0005(14) 0.0324(14) C14 0.0326(13) 0.0478(16) 0.058(2) 0.0115(15) 0.0013(14) 0.0255(13) C15 0.0323(13) 0.0605(17) 0.0394(16) 0.0057(15) -0.0057(12) 0.0228(13) C16 0.0372(13) 0.0417(14) 0.0317(15) -0.0043(12) -0.0041(12) 0.0189(11) C1L 0.13(2) 0.55(8) 0.21(3) 0.000 0.000 0.16(4) Cl1 0.226(7) 0.212(7) 0.503(18) -0.103(8) 0.015(12) 0.027(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 C1 C11 1.515(3) . ? C1 C2 1.548(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N21 1.461(3) . ? C2 C3 1.527(3) . ? C2 H2 1.0000 . ? N21 H21A 0.81(4) . ? N21 H21B 0.90(3) . ? C3 O31 1.239(3) . ? C3 N4 1.337(3) . ? N4 C5 1.452(3) . ? N4 H4 0.91(3) . ? C5 C5 1.526(4) 4_665 ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C11 C12 1.383(4) . ? C11 C16 1.390(4) . ? C12 C13 1.385(4) . ? C12 H12 0.9500 . ? C13 C14 1.379(4) . ? C13 H13 0.9500 . ? C14 C15 1.375(4) . ? C14 H14 0.9500 . ? C15 C16 1.389(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C1L Cl1 1.653(9) . ? C1L Cl1 1.653(9) 4 ? C1L Cl1 2.01(2) 3 ? C1L Cl1 2.01(2) 6 ? C1L H1L 0.9600 . ? Cl1 C1L 2.01(2) 2_554 ? 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 C11 C1 C2 115.29(17) . . ? C11 C1 H1A 108.5 . . ? C2 C1 H1A 108.5 . . ? C11 C1 H1B 108.5 . . ? C2 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? N21 C2 C3 111.37(18) . . ? N21 C2 C1 112.15(19) . . ? C3 C2 C1 107.82(17) . . ? N21 C2 H2 108.5 . . ? C3 C2 H2 108.5 . . ? C1 C2 H2 108.5 . . ? C2 N21 H21A 118(3) . . ? C2 N21 H21B 110.9(16) . . ? H21A N21 H21B 105(3) . . ? O31 C3 N4 124.1(2) . . ? O31 C3 C2 120.51(18) . . ? N4 C3 C2 115.3(2) . . ? C3 N4 C5 122.8(2) . . ? C3 N4 H4 116.2(16) . . ? C5 N4 H4 120.9(16) . . ? N4 C5 C5 111.66(16) . 4_665 ? N4 C5 H5A 109.3 . . ? C5 C5 H5A 109.3 4_665 . ? N4 C5 H5B 109.3 . . ? C5 C5 H5B 109.3 4_665 . ? H5A C5 H5B 107.9 . . ? C12 C11 C16 118.2(2) . . ? C12 C11 C1 121.5(2) . . ? C16 C11 C1 120.3(2) . . ? C11 C12 C13 120.7(3) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 119.6(2) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 119.9(3) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C11 121.0(3) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? Cl1 C1L Cl1 126.8(17) . 4 ? Cl1 C1L Cl1 129.2(5) . 3 ? Cl1 C1L Cl1 88.4(4) 4 3 ? Cl1 C1L Cl1 88.4(4) . 6 ? Cl1 C1L Cl1 129.2(5) 4 6 ? Cl1 C1L Cl1 94.9(9) 3 6 ? Cl1 C1L H1L 105.6 . . ? Cl1 C1L H1L 105.5 4 . ? Cl1 C1L H1L 23.6 3 . ? Cl1 C1L H1L 96.0 6 . ? C1L Cl1 C1L 69.1(5) . 2_554 ? 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 C11 C1 C2 N21 70.8(3) . . . . ? C11 C1 C2 C3 -52.1(3) . . . . ? N21 C2 C3 O31 172.11(19) . . . . ? C1 C2 C3 O31 -64.5(2) . . . . ? N21 C2 C3 N4 -8.0(3) . . . . ? C1 C2 C3 N4 115.4(2) . . . . ? O31 C3 N4 C5 4.7(3) . . . . ? C2 C3 N4 C5 -175.14(18) . . . . ? C3 N4 C5 C5 93.4(2) . . . 4_665 ? C2 C1 C11 C12 -81.3(3) . . . . ? C2 C1 C11 C16 99.7(2) . . . . ? C16 C11 C12 C13 -0.2(4) . . . . ? C1 C11 C12 C13 -179.2(3) . . . . ? C11 C12 C13 C14 0.6(5) . . . . ? C12 C13 C14 C15 -1.0(4) . . . . ? C13 C14 C15 C16 0.9(4) . . . . ? C14 C15 C16 C11 -0.4(4) . . . . ? C12 C11 C16 C15 0.0(4) . . . . ? C1 C11 C16 C15 179.1(2) . . . . ? Cl1 C1L Cl1 C1L 0.000(4) 4 . . 2_554 ? Cl1 C1L Cl1 C1L -124.6(11) 3 . . 2_554 ? Cl1 C1L Cl1 C1L 140.3(3) 6 . . 2_554 ? 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 N4 H4 N21 0.91(3) 2.15(3) 2.643(3) 112.9(19) . N21 H21A O31 0.81(4) 2.43(4) 3.231(3) 170(3) 5_665 N21 H21B O31 0.90(3) 2.19(3) 3.063(3) 167(2) 1_556 _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.202 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.051