data_global _audit_creation_method 'APEX2 v2012.4-3' _publ_requested_journal ? _publ_contact_author_name ? _publ_contact_author_address ; ; _publ_contact_author_email ? _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_section_title ; ; _publ_section_abstract ; ; _publ_section_references ; ; _publ_section_comment ; ; data_I _chemical_name_systematic ? _chemical_name_common Hamada_F24_22_04_12 _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 Cl N5 O4' _chemical_formula_iupac ? _chemical_formula_weight 425.83 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.918(4) _cell_length_b 6.6325(8) _cell_length_c 24.125(3) _cell_angle_alpha 90 _cell_angle_beta 113.965(9) _cell_angle_gamma 90 _cell_volume 4082.0(9) _cell_formula_units_Z 8 _cell_measurement_reflns_used 2411 _cell_measurement_theta_min 6.2833 _cell_measurement_theta_max 62.8777 _cell_measurement_temperature 296.(2) _exptl_crystal_description Flakes _exptl_crystal_colour 'clear light orange' _exptl_crystal_size_max 0.290 _exptl_crystal_size_mid 0.090 _exptl_crystal_size_min 0.010 _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 1.985 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS Inc.)' _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_T_max 0.99 _exptl_special_details ; ; _diffrn_ambient_temperature 296.(2) _diffrn_source ? _diffrn_source_type 'Incoatec Cu-ImS' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_monochromator 'mirror optics' _diffrn_measurement_device_type 'Bruker X8 Prospector' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 11188 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_theta_min 4.01 _diffrn_reflns_theta_max 66.59 _diffrn_reflns_theta_full 66.59 _diffrn_measured_fraction_theta_max 0.955 _diffrn_measured_fraction_theta_full 0.955 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 28 _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. ; _reflns_number_total 3434 _reflns_number_gt 2116 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1154 _refine_ls_R_factor_gt 0.0781 _refine_ls_wR_factor_gt 0.1746 _refine_ls_wR_factor_ref 0.1984 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.133 _refine_ls_number_reflns 3434 _refine_ls_number_parameters 293 _refine_ls_number_restraints 74 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0748P)^2^+5.8219P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.277 _refine_diff_density_min -0.306 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00015(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Instrument Service v2011.2.0.0' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _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 O O4 0.57265(13) 0.7908(7) -0.0900(2) 0.1417(15) Uani d DU 1.0 . . C C17A 0.5232(6) 0.823(3) -0.1478(9) 0.150(3) Uani d PDU 0.413(10) A 1 H H17A 0.5136 0.6887 -0.1649 0.18 Uiso calc PR 0.413(10) A 1 H H17B 0.4965 0.8607 -0.1336 0.18 Uiso calc PR 0.413(10) A 1 C C18A 0.5170(7) 0.907(3) -0.1815(8) 0.160(4) Uani d PDU 0.413(10) A 1 H H18A 0.5056 1.0369 -0.1742 0.24 Uiso calc PR 0.413(10) A 1 H H18B 0.4905 0.8481 -0.217 0.24 Uiso calc PR 0.413(10) A 1 H H18C 0.5489 0.9215 -0.1874 0.24 Uiso calc PR 0.413(10) A 1 C C17B 0.5213(4) 0.917(2) -0.1184(8) 0.154(3) Uani d PDU 0.587(10) A 2 H H17C 0.4966 0.8387 -0.1518 0.184 Uiso calc PR 0.587(10) A 2 H H17D 0.5069 0.9264 -0.0881 0.184 Uiso calc PR 0.587(10) A 2 C C18B 0.5215(5) 1.056(2) -0.1341(7) 0.160(4) Uani d PDU 0.587(10) A 2 H H18D 0.5392 1.1458 -0.1006 0.24 Uiso calc PR 0.587(10) A 2 H H18E 0.4861 1.1016 -0.156 0.24 Uiso calc PR 0.587(10) A 2 H H18F 0.5395 1.056 -0.1605 0.24 Uiso calc PR 0.587(10) A 2 Cl Cl1 0.93084(4) 0.1044(2) 0.22845(6) 0.1058(5) Uani d . 1.0 . . O O1 0.68772(14) -0.7377(6) 0.24621(18) 0.1148(13) Uani d . 1.0 . . N N4 0.71748(11) 0.5618(5) 0.03286(13) 0.0574(8) Uani d . 1.0 . . C C5 0.71696(14) 0.3896(6) 0.06155(16) 0.0558(9) Uani d . 1.0 . . N N2 0.67376(12) 0.1178(5) 0.08832(14) 0.0644(9) Uani d . 1.0 . . N N3 0.63154(12) 0.0266(5) 0.07644(15) 0.0719(9) Uani d . 1.0 . . C C1 0.86832(15) 0.1853(7) 0.18120(18) 0.0679(11) Uani d . 1.0 . . C C2 0.83429(16) 0.0508(7) 0.14164(19) 0.0707(11) Uani d . 1.0 . . H H2 0.8444 -0.0821 0.1405 0.085 Uiso calc R 1.0 . . C C3 0.78453(15) 0.1149(6) 0.10328(18) 0.0656(10) Uani d . 1.0 . . H H3 0.7612 0.0235 0.0767 0.079 Uiso calc R 1.0 . . C C4 0.76913(13) 0.3130(6) 0.10398(15) 0.0542(9) Uani d . 1.0 . . C C6 0.67021(14) 0.2901(6) 0.05318(17) 0.0611(10) Uani d . 1.0 . . C C7 0.63754(14) -0.1482(6) 0.11322(18) 0.0642(10) Uani d . 1.0 . . C C8 0.59271(15) -0.2623(7) 0.1006(2) 0.0740(12) Uani d . 1.0 . . H H7 0.561 -0.2203 0.0707 0.089 Uiso calc R 1.0 . . C C9 0.59496(15) -0.4367(7) 0.1319(2) 0.0763(12) Uani d . 1.0 . . H H8 0.5649 -0.513 0.124 0.092 Uiso calc R 1.0 . . C C10 0.64245(14) -0.4969(6) 0.17539(18) 0.0639(10) Uani d . 1.0 . . N N1 0.64571(15) -0.6855(6) 0.20798(18) 0.0796(10) Uani d . 1.0 . . C C15 0.67202(14) 0.6443(6) -0.00658(17) 0.0606(10) Uani d . 1.0 A . C C14 0.62290(14) 0.5508(7) -0.01813(19) 0.0703(11) Uani d . 1.0 . . C C13 0.62373(15) 0.3754(7) 0.01239(19) 0.0710(11) Uani d . 1.0 A . H H13 0.5922 0.3115 0.0056 0.085 Uiso calc R 1.0 . . O O2 0.60588(14) -0.7863(5) 0.19500(18) 0.1127(13) Uani d . 1.0 . . C C11 0.68733(15) -0.3857(7) 0.1891(2) 0.0750(12) Uani d . 1.0 . . H H15 0.7189 -0.4282 0.2193 0.09 Uiso calc R 1.0 . . C C12 0.68486(15) -0.2129(7) 0.15789(19) 0.0769(12) Uani d . 1.0 . . H H16 0.7151 -0.1372 0.1664 0.092 Uiso calc R 1.0 . . N N5 0.67706(12) 0.8169(5) -0.03278(15) 0.0706(9) Uani d . 1.0 . . H H5A 0.7077 0.8673 -0.0241 0.085 Uiso calc R 1.0 A . H H5B 0.6497 0.877 -0.0583 0.085 Uiso calc R 1.0 . . C C19 0.80425(14) 0.4448(6) 0.14528(17) 0.0662(11) Uani d . 1.0 . . H H19 0.7945 0.578 0.1468 0.079 Uiso calc R 1.0 . . C C20 0.85382(16) 0.3805(7) 0.18440(18) 0.0737(12) Uani d . 1.0 . . H H20 0.8769 0.4691 0.2125 0.088 Uiso calc R 1.0 . . C C16 0.57099(18) 0.6257(10) -0.0603(3) 0.1129(16) Uani d U 1.0 A . O O3 0.53077(13) 0.5465(7) -0.0673(2) 0.1430(17) Uani d U 1.0 . . 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 O4 0.0649(18) 0.134(3) 0.173(3) -0.0021(19) -0.006(2) 0.074(2) C17A 0.078(3) 0.134(5) 0.175(5) 0.012(4) -0.011(4) 0.067(4) C18A 0.102(6) 0.149(7) 0.171(6) 0.012(6) -0.005(6) 0.060(5) C17B 0.081(3) 0.141(5) 0.177(5) 0.007(3) -0.012(4) 0.069(4) C18B 0.103(5) 0.131(6) 0.183(7) 0.023(5) -0.007(5) 0.053(5) Cl1 0.0634(7) 0.1238(12) 0.1060(9) 0.0139(7) 0.0097(6) 0.0046(8) O1 0.079(2) 0.113(3) 0.124(3) 0.002(2) 0.013(2) 0.051(2) N4 0.0491(17) 0.062(2) 0.0576(17) -0.0088(15) 0.0182(14) -0.0014(15) C5 0.053(2) 0.062(2) 0.054(2) -0.0074(18) 0.0227(17) -0.0055(18) N2 0.0547(18) 0.069(2) 0.0701(19) -0.0125(16) 0.0255(16) 0.0038(17) N3 0.0559(19) 0.077(2) 0.082(2) -0.0116(17) 0.0270(17) 0.0122(19) C1 0.052(2) 0.081(3) 0.067(2) 0.000(2) 0.0198(19) -0.001(2) C2 0.066(2) 0.062(2) 0.081(3) 0.001(2) 0.028(2) -0.005(2) C3 0.058(2) 0.065(3) 0.070(2) -0.0108(19) 0.0220(19) -0.013(2) C4 0.051(2) 0.060(2) 0.0514(19) -0.0105(17) 0.0208(16) -0.0036(18) C6 0.051(2) 0.068(3) 0.062(2) -0.0108(19) 0.0211(18) -0.001(2) C7 0.052(2) 0.071(3) 0.072(2) -0.0064(19) 0.0275(19) 0.008(2) C8 0.047(2) 0.083(3) 0.085(3) -0.006(2) 0.020(2) 0.020(2) C9 0.051(2) 0.080(3) 0.095(3) -0.011(2) 0.026(2) 0.017(3) C10 0.055(2) 0.064(2) 0.075(2) -0.0002(18) 0.028(2) 0.012(2) N1 0.071(2) 0.076(3) 0.093(3) -0.001(2) 0.034(2) 0.013(2) C15 0.054(2) 0.063(2) 0.063(2) -0.0072(18) 0.0225(18) -0.0028(19) C14 0.050(2) 0.080(3) 0.076(3) -0.009(2) 0.021(2) 0.004(2) C13 0.053(2) 0.079(3) 0.078(3) -0.014(2) 0.024(2) 0.004(2) O2 0.081(2) 0.097(3) 0.149(3) -0.013(2) 0.034(2) 0.041(2) C11 0.051(2) 0.081(3) 0.081(3) -0.004(2) 0.015(2) 0.013(2) C12 0.050(2) 0.085(3) 0.084(3) -0.014(2) 0.016(2) 0.011(3) N5 0.0556(19) 0.065(2) 0.082(2) -0.0061(16) 0.0187(17) 0.0086(18) C19 0.059(2) 0.063(2) 0.068(2) -0.0087(19) 0.018(2) -0.011(2) C20 0.058(2) 0.081(3) 0.069(2) -0.011(2) 0.011(2) -0.013(2) C16 0.050(2) 0.127(4) 0.139(4) -0.002(2) 0.015(2) 0.055(3) O3 0.0520(18) 0.167(4) 0.177(4) -0.010(2) 0.013(2) 0.070(3) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O4 C16 . 1.319(6) ? O4 C17A . 1.527(12) ? O4 C17B . 1.558(10) ? C17A C18A . 0.943(15) ? C17A H17A . 0.97 ? C17A H17B . 0.97 ? C18A H18A . 0.96 ? C18A H18B . 0.96 ? C18A H18C . 0.96 ? C17B C18B . 1.000(12) ? C17B H17C . 0.97 ? C17B H17D . 0.97 ? C18B H18D . 0.96 ? C18B H18E . 0.96 ? C18B H18F . 0.96 ? Cl1 C1 . 1.737(4) ? O1 N1 . 1.211(4) ? N4 C5 . 1.338(4) ? N4 C15 . 1.354(5) ? C5 C6 . 1.402(5) ? C5 C4 . 1.489(5) ? N2 N3 . 1.250(4) ? N2 C6 . 1.402(5) ? N3 C7 . 1.428(5) ? C1 C20 . 1.368(6) ? C1 C2 . 1.368(6) ? C2 C3 . 1.386(5) ? C2 H2 . 0.93 ? C3 C4 . 1.385(5) ? C3 H3 . 0.93 ? C4 C19 . 1.387(5) ? C6 C13 . 1.391(5) ? C7 C8 . 1.387(5) ? C7 C12 . 1.391(5) ? C8 C9 . 1.370(5) ? C8 H7 . 0.93 ? C9 C10 . 1.373(5) ? C9 H8 . 0.93 ? C10 C11 . 1.373(5) ? C10 N1 . 1.461(5) ? N1 O2 . 1.224(4) ? C15 N5 . 1.342(5) ? C15 C14 . 1.425(5) ? C14 C13 . 1.372(6) ? C14 C16 . 1.478(6) ? C13 H13 . 0.93 ? C11 C12 . 1.358(6) ? C11 H15 . 0.93 ? C12 H16 . 0.93 ? N5 H5A . 0.86 ? N5 H5B . 0.86 ? C19 C20 . 1.388(5) ? C19 H19 . 0.93 ? C20 H20 . 0.93 ? C16 O3 . 1.188(5) ? 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 C16 O4 C17A . . 113.1(8) ? C16 O4 C17B . . 117.1(6) ? C17A O4 C17B . . 36.3(10) ? C18A C17A O4 . . 130.4(19) ? C18A C17A H17A . . 104.7 ? O4 C17A H17A . . 104.7 ? C18A C17A H17B . . 104.7 ? O4 C17A H17B . . 104.7 ? H17A C17A H17B . . 105.7 ? C18B C17B O4 . . 121.1(13) ? C18B C17B H17C . . 107.1 ? O4 C17B H17C . . 107.1 ? C18B C17B H17D . . 107.1 ? O4 C17B H17D . . 107.1 ? H17C C17B H17D . . 106.8 ? C17B C18B H18D . . 109.5 ? C17B C18B H18E . . 109.5 ? H18D C18B H18E . . 109.5 ? C17B C18B H18F . . 109.5 ? H18D C18B H18F . . 109.5 ? H18E C18B H18F . . 109.5 ? C5 N4 C15 . . 120.3(3) ? N4 C5 C6 . . 122.1(3) ? N4 C5 C4 . . 115.7(3) ? C6 C5 C4 . . 122.1(3) ? N3 N2 C6 . . 115.3(3) ? N2 N3 C7 . . 112.9(3) ? C20 C1 C2 . . 121.2(4) ? C20 C1 Cl1 . . 119.8(3) ? C2 C1 Cl1 . . 119.0(3) ? C1 C2 C3 . . 119.3(4) ? C1 C2 H2 . . 120.3 ? C3 C2 H2 . . 120.3 ? C4 C3 C2 . . 121.0(4) ? C4 C3 H3 . . 119.5 ? C2 C3 H3 . . 119.5 ? C3 C4 C19 . . 118.3(3) ? C3 C4 C5 . . 122.5(3) ? C19 C4 C5 . . 119.2(3) ? C13 C6 C5 . . 117.2(4) ? C13 C6 N2 . . 125.2(3) ? C5 C6 N2 . . 117.6(3) ? C8 C7 C12 . . 119.4(4) ? C8 C7 N3 . . 116.1(3) ? C12 C7 N3 . . 124.5(3) ? C9 C8 C7 . . 120.3(4) ? C9 C8 H7 . . 119.8 ? C7 C8 H7 . . 119.8 ? C8 C9 C10 . . 118.7(4) ? C8 C9 H8 . . 120.6 ? C10 C9 H8 . . 120.6 ? C11 C10 C9 . . 122.1(4) ? C11 C10 N1 . . 118.6(4) ? C9 C10 N1 . . 119.3(4) ? O1 N1 O2 . . 122.5(4) ? O1 N1 C10 . . 118.9(4) ? O2 N1 C10 . . 118.6(4) ? N5 C15 N4 . . 115.3(3) ? N5 C15 C14 . . 123.7(4) ? N4 C15 C14 . . 121.0(4) ? C13 C14 C15 . . 117.3(4) ? C13 C14 C16 . . 116.9(4) ? C15 C14 C16 . . 125.8(4) ? C14 C13 C6 . . 122.2(4) ? C14 C13 H13 . . 118.9 ? C6 C13 H13 . . 118.9 ? C12 C11 C10 . . 118.9(4) ? C12 C11 H15 . . 120.5 ? C10 C11 H15 . . 120.5 ? C11 C12 C7 . . 120.6(4) ? C11 C12 H16 . . 119.7 ? C7 C12 H16 . . 119.7 ? C15 N5 H5A . . 120.0 ? C15 N5 H5B . . 120.0 ? H5A N5 H5B . . 120.0 ? C4 C19 C20 . . 120.9(4) ? C4 C19 H19 . . 119.5 ? C20 C19 H19 . . 119.5 ? C1 C20 C19 . . 119.2(4) ? C1 C20 H20 . . 120.4 ? C19 C20 H20 . . 120.4 ? O3 C16 O4 . . 122.0(5) ? O3 C16 C14 . . 123.7(5) ? O4 C16 C14 . . 114.3(4) ?