# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data__soeta7 _database_code_depnum_ccdc_archive 'CCDC 911829' #TrackingRef 'web_deposit_cif_file_0_TakahiroSoeta_1353468101.soeta7.cif' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C21 H24 N6 O ' _chemical_formula_moiety 'C21 H24 N6 O ' _chemical_formula_weight 376.46 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_Int_Tables_number 14 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 _cell_length_a 10.2116(7) _cell_length_b 19.269(1) _cell_length_c 10.7192(7) _cell_angle_alpha 90 _cell_angle_beta 113.424(1) _cell_angle_gamma 90 _cell_volume 1935.4(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7622 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 123.2 #------------------------------------------------------------------------------ _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.084 _exptl_crystal_F_000 800.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_absorpt_correction_T_min 0.806 _exptl_absorpt_correction_T_max 0.983 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_ambient_temperature 123.2 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.46 _diffrn_reflns_number 4503 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.9847 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.9847 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4367 _reflns_number_gt 3362 _reflns_threshold_expression F^2^>3.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.0738 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 3362 _refine_ls_number_parameters 253 _refine_ls_goodness_of_fit_ref 1.294 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00198|Fo|^2^]' _refine_ls_shift/su_max 0.0003 _refine_diff_density_max 0.34 _refine_diff_density_min -0.17 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.1059(2) 0.07405(7) 0.1174(1) 0.0290(4) Uani 1.00 d . . . N1 N 0.8910(2) 0.05913(8) 0.2033(1) 0.0196(4) Uani 1.00 d . . . N2 N 1.0168(2) 0.01856(8) 0.2539(1) 0.0209(4) Uani 1.00 d . . . N3 N 1.0255(2) 0.08477(8) 0.5526(1) 0.0200(4) Uani 1.00 d . . . N4 N 1.1402(2) 0.12239(8) 0.6327(1) 0.0218(4) Uani 1.00 d . . . N5 N 1.1632(2) 0.17243(8) 0.5634(1) 0.0213(4) Uani 1.00 d . . . N6 N 1.0619(1) 0.16882(7) 0.4351(1) 0.0179(3) Uani 1.00 d . . . C1 C 0.8536(2) 0.08068(9) 0.3164(2) 0.0183(4) Uani 1.00 d . . . C2 C 0.7191(2) 0.12449(9) 0.2646(2) 0.0192(4) Uani 1.00 d . . . C3 C 0.6889(2) 0.1677(1) 0.3542(2) 0.0245(4) Uani 1.00 d . . . C4 C 0.5656(2) 0.2073(1) 0.3096(2) 0.0277(5) Uani 1.00 d . . . C5 C 0.4707(2) 0.2037(1) 0.1749(2) 0.0278(5) Uani 1.00 d . . . C6 C 0.4988(2) 0.1601(1) 0.0860(2) 0.0258(5) Uani 1.00 d . . . C7 C 0.6233(2) 0.11996(9) 0.1291(2) 0.0215(4) Uani 1.00 d . . . C8 C 0.6545(2) 0.0742(1) 0.0295(2) 0.0268(5) Uani 1.00 d . . . C9 C 0.7706(2) 0.02137(10) 0.1014(2) 0.0242(4) Uani 1.00 d . . . C10 C 0.9783(2) 0.11349(9) 0.4298(2) 0.0175(4) Uani 1.00 d . . . C11 C 1.0717(2) 0.22559(9) 0.3408(2) 0.0191(4) Uani 1.00 d . . . C12 C 1.2140(2) 0.21462(10) 0.3272(2) 0.0235(4) Uani 1.00 d . . . C13 C 0.9477(2) 0.22110(10) 0.2025(2) 0.0238(4) Uani 1.00 d . . . C14 C 1.0684(2) 0.29487(10) 0.4088(2) 0.0257(5) Uani 1.00 d . . . C15 C 1.1173(2) 0.02986(9) 0.2025(2) 0.0206(4) Uani 1.00 d . . . C16 C 1.2470(2) -0.01536(9) 0.2612(2) 0.0205(4) Uani 1.00 d . . . C17 C 1.3788(2) 0.0138(1) 0.2810(2) 0.0277(5) Uani 1.00 d . . . C18 C 1.5013(2) -0.0260(1) 0.3332(2) 0.0336(5) Uani 1.00 d . . . C19 C 1.4933(2) -0.0956(1) 0.3626(2) 0.0347(5) Uani 1.00 d . . . C20 C 1.3632(2) -0.1250(1) 0.3424(2) 0.0321(5) Uani 1.00 d . . . C21 C 1.2399(2) -0.08483(10) 0.2928(2) 0.0252(5) Uani 1.00 d . . . H1 H 0.8394 0.0366 0.3673 0.0912 Uiso 1.00 calc . . . H2 H 0.7600 0.1705 0.4524 0.0912 Uiso 1.00 calc . . . H3 H 0.5517 0.2374 0.3817 0.0912 Uiso 1.00 calc . . . H4 H 0.3874 0.2329 0.1434 0.0912 Uiso 1.00 calc . . . H5 H 0.4322 0.1546 -0.0090 0.0912 Uiso 1.00 calc . . . H6 H 0.6893 0.1031 -0.0282 0.0912 Uiso 1.00 calc . . . H7 H 0.5675 0.0513 -0.0321 0.0912 Uiso 1.00 calc . . . H8 H 0.8078 0.0050 0.0350 0.0912 Uiso 1.00 calc . . . H9 H 0.7393 -0.0166 0.1529 0.0912 Uiso 1.00 calc . . . H10 H 1.2166 0.1682 0.2786 0.0912 Uiso 1.00 calc . . . H11 H 1.2301 0.2546 0.2676 0.0912 Uiso 1.00 calc . . . H12 H 1.2901 0.2160 0.4136 0.0912 Uiso 1.00 calc . . . H13 H 0.9685 0.2651 0.1443 0.0912 Uiso 1.00 calc . . . H14 H 0.8556 0.2340 0.2201 0.0912 Uiso 1.00 calc . . . H15 H 0.9428 0.1782 0.1543 0.0912 Uiso 1.00 calc . . . H16 H 0.9681 0.3016 0.4159 0.0912 Uiso 1.00 calc . . . H17 H 1.0693 0.3318 0.3438 0.0912 Uiso 1.00 calc . . . H18 H 1.1466 0.2991 0.5032 0.0912 Uiso 1.00 calc . . . H19 H 1.0242 -0.0192 0.3163 0.0912 Uiso 1.00 calc . . . H20 H 1.3814 0.0661 0.2561 0.0912 Uiso 1.00 calc . . . H21 H 1.5901 0.0041 0.3491 0.0912 Uiso 1.00 calc . . . H22 H 1.5837 -0.1184 0.3973 0.0912 Uiso 1.00 calc . . . H23 H 1.3545 -0.1708 0.3730 0.0912 Uiso 1.00 calc . . . H24 H 1.1504 -0.1059 0.2808 0.0912 Uiso 1.00 calc . . . 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 O1 0.0342(7) 0.0273(7) 0.0331(7) 0.0077(6) 0.0213(6) 0.0087(6) N1 0.0168(7) 0.0230(7) 0.0186(7) 0.0044(6) 0.0065(6) -0.0004(6) N2 0.0201(7) 0.0215(8) 0.0233(7) 0.0050(6) 0.0107(6) 0.0040(6) N3 0.0191(7) 0.0221(7) 0.0184(7) 0.0022(6) 0.0070(6) 0.0021(6) N4 0.0215(7) 0.0233(8) 0.0197(7) 0.0017(6) 0.0073(6) 0.0014(6) N5 0.0205(7) 0.0239(8) 0.0174(7) 0.0018(6) 0.0055(6) 0.0022(6) N6 0.0153(7) 0.0207(7) 0.0169(7) 0.0013(5) 0.0056(6) 0.0012(5) C1 0.0168(8) 0.0205(8) 0.0182(8) 0.0006(6) 0.0074(7) 0.0006(6) C2 0.0156(8) 0.0207(8) 0.0223(8) -0.0007(6) 0.0088(7) 0.0022(6) C3 0.0196(9) 0.0290(10) 0.0244(9) 0.0019(7) 0.0083(7) -0.0007(7) C4 0.0247(9) 0.031(1) 0.0303(10) 0.0047(8) 0.0139(8) -0.0003(8) C5 0.0190(9) 0.032(1) 0.033(1) 0.0056(7) 0.0109(8) 0.0074(8) C6 0.0191(9) 0.0312(10) 0.0259(9) 0.0006(7) 0.0075(7) 0.0053(8) C7 0.0181(8) 0.0243(9) 0.0217(8) -0.0012(6) 0.0076(7) 0.0025(7) C8 0.0231(9) 0.034(1) 0.0202(9) 0.0045(7) 0.0053(7) -0.0012(7) C9 0.0246(9) 0.0254(9) 0.0204(8) 0.0013(7) 0.0065(7) -0.0037(7) C10 0.0163(8) 0.0188(8) 0.0190(8) 0.0031(6) 0.0089(7) 0.0014(6) C11 0.0203(8) 0.0193(8) 0.0188(8) 0.0000(6) 0.0091(7) 0.0043(6) C12 0.0204(9) 0.0277(9) 0.0240(9) 0.0019(7) 0.0104(7) 0.0029(7) C13 0.0221(9) 0.0265(9) 0.0202(8) -0.0003(7) 0.0057(7) 0.0040(7) C14 0.0306(10) 0.0209(9) 0.0251(9) 0.0029(7) 0.0108(8) 0.0016(7) C15 0.0233(9) 0.0200(8) 0.0208(8) 0.0010(7) 0.0111(7) -0.0016(6) C16 0.0208(9) 0.0240(9) 0.0185(8) 0.0014(7) 0.0098(7) -0.0020(7) C17 0.0242(9) 0.030(1) 0.0298(10) -0.0033(8) 0.0121(8) -0.0011(8) C18 0.0218(9) 0.044(1) 0.035(1) -0.0020(8) 0.0115(8) 0.0019(9) C19 0.0246(10) 0.047(1) 0.034(1) 0.0123(9) 0.0126(9) 0.0104(9) C20 0.033(1) 0.030(1) 0.040(1) 0.0080(8) 0.0212(9) 0.0102(8) C21 0.0225(9) 0.0231(9) 0.0333(10) 0.0011(7) 0.0145(8) 0.0007(8) #------------------------------------------------------------------------------ _computing_data_collection CRYSTALCLEAR _computing_cell_refinement CRYSTALCLEAR _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C15 1.220(2) . . yes N1 N2 1.415(2) . . yes N1 C1 1.469(2) . . yes N1 C9 1.472(2) . . yes N2 C15 1.361(2) . . yes N3 N4 1.355(2) . . yes N3 C10 1.329(2) . . yes N4 N5 1.294(2) . . yes N5 N6 1.355(2) . . yes N6 C10 1.352(2) . . yes N6 C11 1.520(2) . . yes C1 C2 1.517(2) . . yes C1 C10 1.506(2) . . yes C2 C3 1.394(2) . . yes C2 C7 1.395(2) . . yes C3 C4 1.385(3) . . yes C4 C5 1.385(3) . . yes C5 C6 1.385(3) . . yes C6 C7 1.400(2) . . yes C7 C8 1.513(3) . . yes C8 C9 1.519(3) . . yes C11 C12 1.532(2) . . yes C11 C13 1.522(2) . . yes C11 C14 1.528(2) . . yes C15 C16 1.499(2) . . yes C16 C17 1.395(3) . . yes C16 C21 1.390(3) . . yes C17 C18 1.383(3) . . yes C18 C19 1.386(3) . . yes C19 C20 1.380(3) . . yes C20 C21 1.391(3) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C1 109.5(1) . . . yes N2 N1 C9 112.0(1) . . . yes C1 N1 C9 109.7(1) . . . yes N1 N2 C15 118.2(1) . . . yes N4 N3 C10 106.6(1) . . . yes N3 N4 N5 110.1(1) . . . yes N4 N5 N6 107.7(1) . . . yes N5 N6 C10 107.3(1) . . . yes N5 N6 C11 114.4(1) . . . yes C10 N6 C11 138.3(1) . . . yes N1 C1 C2 110.5(1) . . . yes N1 C1 C10 111.8(1) . . . yes C2 C1 C10 114.5(1) . . . yes C1 C2 C3 119.7(1) . . . yes C1 C2 C7 120.3(1) . . . yes C3 C2 C7 119.9(2) . . . yes C2 C3 C4 120.7(2) . . . yes C3 C4 C5 119.7(2) . . . yes C4 C5 C6 119.8(2) . . . yes C5 C6 C7 121.2(2) . . . yes C2 C7 C6 118.6(2) . . . yes C2 C7 C8 120.9(2) . . . yes C6 C7 C8 120.5(2) . . . yes C7 C8 C9 111.9(1) . . . yes N1 C9 C8 107.3(1) . . . yes N3 C10 N6 108.2(1) . . . yes N3 C10 C1 118.8(1) . . . yes N6 C10 C1 133.0(1) . . . yes N6 C11 C12 106.3(1) . . . yes N6 C11 C13 111.0(1) . . . yes N6 C11 C14 107.0(1) . . . yes C12 C11 C13 110.6(1) . . . yes C12 C11 C14 111.6(1) . . . yes C13 C11 C14 110.3(1) . . . yes O1 C15 N2 123.4(2) . . . yes O1 C15 C16 121.7(1) . . . yes N2 C15 C16 114.8(1) . . . yes C15 C16 C17 117.9(2) . . . yes C15 C16 C21 122.6(2) . . . yes C17 C16 C21 119.5(2) . . . yes C16 C17 C18 120.0(2) . . . yes C17 C18 C19 120.2(2) . . . yes C18 C19 C20 120.1(2) . . . yes C19 C20 C21 120.0(2) . . . yes C16 C21 C20 120.1(2) . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C14 3.293(2) . 4_554 ? O1 C9 3.581(2) . 3_755 ? N2 N3 3.028(2) . 3_756 ? N3 N3 3.427(3) . 3_756 ? N3 C1 3.505(2) . 3_756 ? N5 C12 3.440(2) . 4_555 ? N5 C19 3.594(2) . 3_856 ? C3 C20 3.594(3) . 3_756 ? #------------------------------------------------------------------------------ #===END #------------------------------------------------------------------------------