# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email deba_h76@yahoo.com _publ_contact_author_name 'Debasish Haldar' loop_ _publ_author_name 'Debasish Haldar' 'Poulami Jana' 'Sibaprasad Maity' 'Suman Maity' data_pj _database_code_depnum_ccdc_archive 'CCDC 866281' #TrackingRef '- bisimide 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 N2 O8' _chemical_formula_sum 'C24 H28 N2 O8' _chemical_formula_weight 472.48 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' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.3430(11) _cell_length_b 10.4839(11) _cell_length_c 11.3463(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.229(3) _cell_angle_gamma 90.00 _cell_volume 1230.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5348 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 27.000 _chemical_absolute_configuration syn _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max .4 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details 'SADABS, bruker-2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10770 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5067 _reflns_number_gt 4568 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0672P)^2^+0.4966P] 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 constr _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 0.001(1) _refine_ls_number_reflns 5067 _refine_ls_number_parameters 313 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1260 _refine_ls_wR_factor_gt 0.1211 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.002 _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 C33 C 0.1328(2) 0.8897(2) 0.07477(19) 0.0203(5) Uani 1 1 d . . . H33 H 0.0673 0.9302 0.1153 0.024 Uiso 1 1 calc R . . O2 O 0.10143(16) 0.98564(17) -0.39659(14) 0.0269(4) Uani 1 1 d . . . O3 O 0.2057(2) 1.1342(2) -0.50005(15) 0.0460(6) Uani 1 1 d . . . O4 O 0.05240(16) 1.12467(16) -0.07535(14) 0.0256(4) Uani 1 1 d . . . O5 O 0.09205(15) 0.72720(16) 0.30212(13) 0.0244(4) Uani 1 1 d . . . O6 O 0.3113(3) 0.5143(2) 0.52519(17) 0.0610(8) Uani 1 1 d . . . O7 O 0.37678(16) 0.67539(17) 0.41206(14) 0.0269(4) Uani 1 1 d . . . C31 C 0.0882(3) 0.2829(3) 0.2167(3) 0.0401(7) Uani 1 1 d . . . H31A H 0.0524 0.2334 0.1527 0.060 Uiso 1 1 calc R . . H31B H 0.0436 0.3630 0.2209 0.060 Uiso 1 1 calc R . . H31C H 0.0784 0.2373 0.2893 0.060 Uiso 1 1 calc R . . O9 O 0.42364(17) 0.53659(18) 0.10705(16) 0.0312(4) Uani 1 1 d . . . O10 O 0.37072(15) 0.92860(16) -0.28209(14) 0.0242(4) Uani 1 1 d . . . C29 C 0.3213(2) 1.2406(2) -0.2940(2) 0.0224(5) Uani 1 1 d . . . H29A H 0.3106 1.2965 -0.3617 0.027 Uiso 1 1 calc R . . H29B H 0.3977 1.1891 -0.3063 0.027 Uiso 1 1 calc R . . C27 C 0.4642(2) 1.4073(3) -0.2018(2) 0.0318(6) Uani 1 1 d . . . H27A H 0.4452 1.4699 -0.2615 0.048 Uiso 1 1 calc R . . H27B H 0.5350 1.3551 -0.2261 0.048 Uiso 1 1 calc R . . H27C H 0.4871 1.4495 -0.1292 0.048 Uiso 1 1 calc R . . C25 C 0.3004(3) 0.1802(3) 0.1815(3) 0.0424(7) Uani 1 1 d . . . H25A H 0.2825 0.1258 0.2472 0.064 Uiso 1 1 calc R . . H25B H 0.3919 0.1949 0.1780 0.064 Uiso 1 1 calc R . . H25C H 0.2707 0.1400 0.1099 0.064 Uiso 1 1 calc R . . C23 C 0.2309(3) 0.3067(2) 0.1962(2) 0.0289(5) Uani 1 1 d . . . H23 H 0.2395 0.3565 0.1237 0.035 Uiso 1 1 calc R . . C21 C 0.1924(2) 0.7789(2) 0.11541(19) 0.0203(5) Uani 1 1 d . . . C34 C 0.1371(2) 1.0508(2) -0.09761(18) 0.0182(4) Uani 1 1 d . . . N5 N 0.21672(18) 1.05623(18) -0.19638(16) 0.0195(4) Uani 1 1 d . . . C3 C 0.2907(2) 0.7197(2) 0.05572(19) 0.0200(5) Uani 1 1 d . . . C19 C 0.3369(2) 0.7652(2) -0.05062(19) 0.0205(5) Uani 1 1 d . . . H19 H 0.4027 0.7246 -0.0908 0.025 Uiso 1 1 calc R . . C17 C 0.3445(2) 1.3233(2) -0.1836(2) 0.0275(5) Uani 1 1 d . . . H29 H 0.3614 1.2670 -0.1161 0.033 Uiso 1 1 calc R . . C12 C 0.2286(3) 1.4063(3) -0.1570(3) 0.0363(6) Uani 1 1 d . . . H12A H 0.2497 1.4620 -0.0922 0.054 Uiso 1 1 calc R . . H12B H 0.1568 1.3532 -0.1367 0.054 Uiso 1 1 calc R . . H12C H 0.2059 1.4563 -0.2253 0.054 Uiso 1 1 calc R . . C32 C 0.2996(2) 0.3781(2) 0.2976(2) 0.0268(5) Uani 1 1 d . . . H1A H 0.2931 0.3273 0.3687 0.032 Uiso 1 1 calc R . . H1B H 0.3906 0.3852 0.2798 0.032 Uiso 1 1 calc R . . C20 C 0.2476(3) 0.5113(2) 0.3228(2) 0.0269(5) Uani 1 1 d . . . H25 H 0.1565 0.5006 0.3429 0.032 Uiso 1 1 calc R . . N1 N 0.24955(19) 0.59925(19) 0.22160(17) 0.0226(4) Uani 1 1 d . . . C18 C 0.1665(2) 0.7042(2) 0.2242(2) 0.0216(5) Uani 1 1 d . . . C15 C 0.1789(2) 0.9346(2) -0.03068(19) 0.0192(4) Uani 1 1 d . . . C14 C 0.2045(2) 1.1527(2) -0.2890(2) 0.0212(5) Uani 1 1 d . . . H21 H 0.1301 1.2060 -0.2697 0.025 Uiso 1 1 calc R . . C22 C 0.1739(2) 1.0910(2) -0.4086(2) 0.0256(5) Uani 1 1 d . . . C30 C 0.0693(3) 0.9207(3) -0.5055(2) 0.0447(8) Uani 1 1 d . . . H8A H 0.0169 0.9754 -0.5548 0.067 Uiso 1 1 calc R . . H8B H 0.0223 0.8440 -0.4887 0.067 Uiso 1 1 calc R . . H8C H 0.1473 0.8994 -0.5454 0.067 Uiso 1 1 calc R . . C24 C 0.3345(2) 0.6058(2) 0.1270(2) 0.0224(5) Uani 1 1 d . . . C28 C 0.3154(3) 0.5662(3) 0.4322(2) 0.0318(6) Uani 1 1 d . . . C16 C 0.4396(3) 0.7328(3) 0.5149(2) 0.0389(6) Uani 1 1 d . . . H11A H 0.3800 0.7356 0.5786 0.058 Uiso 1 1 calc R . . H11B H 0.4665 0.8179 0.4961 0.058 Uiso 1 1 calc R . . H11C H 0.5137 0.6829 0.5380 0.058 Uiso 1 1 calc R . . C5 C 0.2777(2) 0.8756(2) -0.09217(19) 0.0187(4) Uani 1 1 d . . . C26 C 0.2998(2) 0.9511(2) -0.20162(19) 0.0190(4) Uani 1 1 d . . . 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 C33 0.0208(10) 0.0193(11) 0.0209(10) -0.0014(9) -0.0001(8) 0.0020(9) O2 0.0345(9) 0.0264(9) 0.0198(8) -0.0044(7) 0.0019(7) -0.0088(7) O3 0.0729(14) 0.0476(13) 0.0173(8) 0.0048(9) -0.0019(9) -0.0287(11) O4 0.0295(8) 0.0255(9) 0.0219(8) 0.0029(7) 0.0026(6) 0.0075(7) O5 0.0281(8) 0.0269(9) 0.0182(7) 0.0000(7) 0.0009(6) -0.0031(7) O6 0.119(2) 0.0394(13) 0.0233(10) 0.0079(9) -0.0215(12) -0.0253(14) O7 0.0316(9) 0.0286(9) 0.0203(8) -0.0027(7) -0.0033(6) -0.0045(8) C31 0.0380(14) 0.0432(17) 0.0387(15) -0.0102(13) -0.0103(11) 0.0093(13) O9 0.0351(9) 0.0287(10) 0.0297(9) 0.0041(8) -0.0003(7) 0.0074(8) O10 0.0264(8) 0.0253(9) 0.0211(8) -0.0012(7) 0.0034(6) 0.0006(7) C29 0.0261(11) 0.0200(11) 0.0212(10) 0.0035(9) -0.0005(8) -0.0025(9) C27 0.0325(12) 0.0290(13) 0.0336(13) 0.0024(11) -0.0090(10) -0.0067(11) C25 0.0350(14) 0.0362(16) 0.0563(18) -0.0139(14) 0.0069(13) -0.0012(13) C23 0.0432(14) 0.0219(12) 0.0215(11) 0.0010(10) -0.0011(10) -0.0041(11) C21 0.0230(10) 0.0191(11) 0.0188(10) -0.0016(9) -0.0034(8) -0.0027(9) C34 0.0197(10) 0.0183(11) 0.0166(10) 0.0013(9) 0.0011(8) 0.0000(9) N5 0.0226(9) 0.0186(10) 0.0172(9) 0.0008(8) 0.0023(7) 0.0000(8) C3 0.0237(10) 0.0168(11) 0.0192(10) 0.0001(9) -0.0063(8) -0.0022(9) C19 0.0225(10) 0.0210(12) 0.0180(10) -0.0016(9) 0.0001(8) -0.0002(9) C17 0.0369(13) 0.0215(12) 0.0240(11) 0.0038(10) -0.0035(9) -0.0049(10) C12 0.0428(14) 0.0271(14) 0.0390(15) -0.0081(12) 0.0018(11) -0.0038(12) C32 0.0309(12) 0.0240(13) 0.0256(12) 0.0060(10) -0.0009(9) -0.0013(10) C20 0.0387(13) 0.0212(12) 0.0207(11) 0.0063(10) -0.0025(10) -0.0026(10) N1 0.0300(10) 0.0196(10) 0.0179(9) 0.0016(8) -0.0052(7) -0.0017(8) C18 0.0256(11) 0.0150(11) 0.0239(11) -0.0011(9) -0.0074(9) -0.0047(9) C15 0.0204(10) 0.0190(11) 0.0181(10) -0.0006(9) -0.0029(8) -0.0005(9) C14 0.0275(11) 0.0168(11) 0.0193(10) 0.0015(8) 0.0006(8) 0.0003(9) C22 0.0341(12) 0.0223(12) 0.0202(11) 0.0026(9) -0.0017(9) -0.0035(10) C30 0.0612(18) 0.0463(19) 0.0264(13) -0.0094(13) -0.0027(12) -0.0232(16) C24 0.0283(12) 0.0178(11) 0.0208(10) -0.0007(9) -0.0054(9) 0.0010(9) C28 0.0495(15) 0.0239(13) 0.0215(12) 0.0020(10) -0.0071(11) -0.0010(12) C16 0.0489(15) 0.0415(17) 0.0258(12) -0.0107(12) -0.0064(11) -0.0094(14) C5 0.0208(10) 0.0172(11) 0.0180(10) -0.0016(8) -0.0006(8) -0.0038(9) C26 0.0198(10) 0.0189(11) 0.0182(10) -0.0017(9) 0.0002(8) -0.0028(8) _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 C33 C15 1.380(3) . ? C33 C21 1.389(3) . ? C33 H33 0.9300 . ? O2 C22 1.343(3) . ? O2 C30 1.444(3) . ? O3 C22 1.185(3) . ? O4 C34 1.200(3) . ? O5 C18 1.209(3) . ? O6 C28 1.188(3) . ? O7 C28 1.331(3) . ? O7 C16 1.454(3) . ? C31 C23 1.520(4) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? O9 C24 1.199(3) . ? O10 C26 1.206(3) . ? C29 C14 1.522(3) . ? C29 C17 1.538(3) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C27 C17 1.537(3) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C25 C23 1.519(4) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C23 C32 1.534(3) . ? C23 H23 0.9800 . ? C21 C3 1.381(3) . ? C21 C18 1.491(3) . ? C34 N5 1.406(3) . ? C34 C15 1.494(3) . ? N5 C26 1.400(3) . ? N5 C14 1.462(3) . ? C3 C19 1.392(3) . ? C3 C24 1.506(3) . ? C19 C5 1.387(3) . ? C19 H19 0.9300 . ? C17 C12 1.517(4) . ? C17 H29 0.9800 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C32 C20 1.526(4) . ? C32 H1A 0.9700 . ? C32 H1B 0.9700 . ? C20 N1 1.473(3) . ? C20 C28 1.525(3) . ? C20 H25 0.9800 . ? N1 C18 1.396(3) . ? N1 C24 1.403(3) . ? C15 C5 1.395(3) . ? C14 C22 1.531(3) . ? C14 H21 0.9800 . ? C30 H8A 0.9600 . ? C30 H8B 0.9600 . ? C30 H8C 0.9600 . ? C16 H11A 0.9600 . ? C16 H11B 0.9600 . ? C16 H11C 0.9600 . ? C5 C26 1.495(3) . ? 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 C15 C33 C21 114.5(2) . . ? C15 C33 H33 122.8 . . ? C21 C33 H33 122.8 . . ? C22 O2 C30 114.8(2) . . ? C28 O7 C16 115.1(2) . . ? C23 C31 H31A 109.5 . . ? C23 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C23 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C14 C29 C17 114.90(19) . . ? C14 C29 H29A 108.5 . . ? C17 C29 H29A 108.5 . . ? C14 C29 H29B 108.5 . . ? C17 C29 H29B 108.5 . . ? H29A C29 H29B 107.5 . . ? C17 C27 H27A 109.5 . . ? C17 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C17 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C25 C23 C31 109.7(2) . . ? C25 C23 C32 107.2(2) . . ? C31 C23 C32 113.6(2) . . ? C25 C23 H23 108.7 . . ? C31 C23 H23 108.7 . . ? C32 C23 H23 108.7 . . ? C3 C21 C33 122.6(2) . . ? C3 C21 C18 108.5(2) . . ? C33 C21 C18 128.9(2) . . ? O4 C34 N5 125.7(2) . . ? O4 C34 C15 128.6(2) . . ? N5 C34 C15 105.67(18) . . ? C26 N5 C34 111.89(18) . . ? C26 N5 C14 123.91(18) . . ? C34 N5 C14 123.90(18) . . ? C21 C3 C19 122.8(2) . . ? C21 C3 C24 108.02(19) . . ? C19 C3 C24 129.2(2) . . ? C5 C19 C3 115.0(2) . . ? C5 C19 H19 122.5 . . ? C3 C19 H19 122.5 . . ? C12 C17 C27 109.9(2) . . ? C12 C17 C29 112.0(2) . . ? C27 C17 C29 109.0(2) . . ? C12 C17 H29 108.6 . . ? C27 C17 H29 108.6 . . ? C29 C17 H29 108.6 . . ? C17 C12 H12A 109.5 . . ? C17 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C17 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C20 C32 C23 115.3(2) . . ? C20 C32 H1A 108.4 . . ? C23 C32 H1A 108.4 . . ? C20 C32 H1B 108.4 . . ? C23 C32 H1B 108.4 . . ? H1A C32 H1B 107.5 . . ? N1 C20 C28 112.6(2) . . ? N1 C20 C32 114.6(2) . . ? C28 C20 C32 109.9(2) . . ? N1 C20 H25 106.4 . . ? C28 C20 H25 106.4 . . ? C32 C20 H25 106.4 . . ? C18 N1 C24 111.91(18) . . ? C18 N1 C20 117.22(19) . . ? C24 N1 C20 130.3(2) . . ? O5 C18 N1 125.1(2) . . ? O5 C18 C21 129.0(2) . . ? N1 C18 C21 105.94(19) . . ? C33 C15 C5 123.5(2) . . ? C33 C15 C34 128.1(2) . . ? C5 C15 C34 108.34(18) . . ? N5 C14 C29 112.93(18) . . ? N5 C14 C22 110.96(19) . . ? C29 C14 C22 111.84(19) . . ? N5 C14 H21 106.9 . . ? C29 C14 H21 106.9 . . ? C22 C14 H21 106.9 . . ? O3 C22 O2 124.7(2) . . ? O3 C22 C14 124.0(2) . . ? O2 C22 C14 111.27(19) . . ? O2 C30 H8A 109.5 . . ? O2 C30 H8B 109.5 . . ? H8A C30 H8B 109.5 . . ? O2 C30 H8C 109.5 . . ? H8A C30 H8C 109.5 . . ? H8B C30 H8C 109.5 . . ? O9 C24 N1 127.7(2) . . ? O9 C24 C3 127.1(2) . . ? N1 C24 C3 105.27(19) . . ? O6 C28 O7 124.9(2) . . ? O6 C28 C20 121.6(2) . . ? O7 C28 C20 113.4(2) . . ? O7 C16 H11A 109.5 . . ? O7 C16 H11B 109.5 . . ? H11A C16 H11B 109.5 . . ? O7 C16 H11C 109.5 . . ? H11A C16 H11C 109.5 . . ? H11B C16 H11C 109.5 . . ? C19 C5 C15 121.5(2) . . ? C19 C5 C26 130.5(2) . . ? C15 C5 C26 107.90(19) . . ? O10 C26 N5 124.8(2) . . ? O10 C26 C5 129.1(2) . . ? N5 C26 C5 106.07(17) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.490 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.049 # Attachment '- bisimide-1.cif' data_jp-1 _database_code_depnum_ccdc_archive 'CCDC 866278' #TrackingRef '- bisimide-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H24 N2 O8' _chemical_formula_sum 'C30 H24 N2 O8' _chemical_formula_weight 540.51 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 13.218(4) _cell_length_b 5.8309(18) _cell_length_c 18.241(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.237(15) _cell_angle_gamma 90.00 _cell_volume 1335.2(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2709 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 21.02 _chemical_absolute_configuration syn _exptl_crystal_description cubic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.434 _exptl_crystal_size_mid 0.083 _exptl_crystal_size_min 0.071 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.099 _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 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12185 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 21.23 _reflns_number_total 1475 _reflns_number_gt 1130 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0376P)^2^+0.5991P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1475 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0983 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.49808(17) 0.3316(4) 0.42485(12) 0.0743(7) Uani 1 1 d . . . O3 O 0.88562(14) 0.4975(3) 0.58024(11) 0.0534(5) Uani 1 1 d . . . O4 O 0.64259(16) 0.4004(3) 0.38910(11) 0.0613(6) Uani 1 1 d . . . C1 C 0.8724(3) 0.1926(8) 0.7925(2) 0.0856(12) Uani 1 1 d . . . H1 H 0.9265 0.2029 0.8395 0.103 Uiso 1 1 calc R . . C2 C 0.8004(3) 0.3635(6) 0.76981(19) 0.0765(10) Uani 1 1 d . . . H2 H 0.8040 0.4900 0.8016 0.092 Uiso 1 1 calc R . . C3 C 0.7222(2) 0.3509(6) 0.70033(17) 0.0614(9) Uani 1 1 d . . . H3 H 0.6741 0.4714 0.6852 0.074 Uiso 1 1 calc R . . C4 C 0.7125(2) 0.1658(5) 0.65200(16) 0.0504(8) Uani 1 1 d . . . C5 C 0.6311(2) 0.1667(5) 0.57307(16) 0.0564(8) Uani 1 1 d . . . H5A H 0.5648 0.2313 0.5759 0.068 Uiso 1 1 calc R . . H5B H 0.6173 0.0108 0.5540 0.068 Uiso 1 1 calc R . . C6 C 0.6716(2) 0.3074(5) 0.51851(15) 0.0474(7) Uani 1 1 d . . . H6 H 0.6873 0.4604 0.5415 0.057 Uiso 1 1 calc R . . N1 N 0.77167(16) 0.2174(4) 0.51320(12) 0.0418(6) Uani 1 1 d . . . C8 C 0.7789(2) 0.0155(5) 0.47491(15) 0.0458(7) Uani 1 1 d . . . C9 C 0.89324(19) -0.0158(4) 0.48329(14) 0.0376(7) Uani 1 1 d . . . C10 C 1.0572(2) 0.1875(5) 0.54470(14) 0.0423(7) Uani 1 1 d . . . H10 H 1.0946 0.3090 0.5739 0.051 Uiso 1 1 calc R . . C11 C 0.9480(2) 0.1660(4) 0.52622(14) 0.0361(7) Uani 1 1 d . . . C12 C 0.8697(2) 0.3190(5) 0.54530(15) 0.0403(7) Uani 1 1 d . . . C13 C 0.7842(3) -0.0107(6) 0.6758(2) 0.0712(9) Uani 1 1 d . . . H13 H 0.7786 -0.1402 0.6450 0.085 Uiso 1 1 calc R . . C14 C 0.8658(3) 0.0047(8) 0.7465(2) 0.0876(12) Uani 1 1 d . . . H14 H 0.9155 -0.1130 0.7620 0.105 Uiso 1 1 calc R . . C15 C 0.5923(3) 0.3412(5) 0.43900(17) 0.0500(8) Uani 1 1 d . . . C16 C 0.5782(3) 0.4739(7) 0.31429(17) 0.0927(12) Uani 1 1 d . . . H16A H 0.5261 0.3583 0.2916 0.139 Uiso 1 1 calc R . . H16B H 0.6224 0.4983 0.2821 0.139 Uiso 1 1 calc R . . H16C H 0.5428 0.6144 0.3189 0.139 Uiso 1 1 calc R . . O2 O 0.70466(15) -0.1043(3) 0.44130(12) 0.0648(6) Uani 1 1 d . . . 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 0.0393(14) 0.1021(18) 0.0698(15) -0.0004(13) 0.0002(11) 0.0031(13) O3 0.0504(12) 0.0479(12) 0.0593(13) -0.0136(11) 0.0132(10) -0.0022(10) O4 0.0606(13) 0.0733(14) 0.0439(12) 0.0006(10) 0.0077(12) 0.0101(11) C1 0.078(3) 0.108(3) 0.059(2) 0.018(3) 0.005(2) 0.001(3) C2 0.085(3) 0.081(3) 0.053(2) 0.0037(19) 0.006(2) 0.001(2) C3 0.065(2) 0.066(2) 0.051(2) 0.0031(18) 0.0140(18) 0.0065(17) C4 0.0438(18) 0.058(2) 0.0505(19) 0.0048(17) 0.0166(15) 0.0015(16) C5 0.0434(18) 0.068(2) 0.057(2) -0.0007(16) 0.0158(16) -0.0021(16) C6 0.0377(17) 0.0528(18) 0.0461(17) -0.0065(14) 0.0051(14) 0.0043(14) N1 0.0333(14) 0.0447(14) 0.0434(13) -0.0078(11) 0.0062(11) -0.0002(11) C8 0.0380(18) 0.0520(19) 0.0402(17) -0.0017(15) 0.0018(14) -0.0042(16) C9 0.0356(16) 0.0397(17) 0.0332(15) 0.0009(13) 0.0047(13) 0.0013(15) C10 0.0432(19) 0.0427(17) 0.0354(15) -0.0014(13) 0.0041(14) -0.0050(15) C11 0.0361(17) 0.0371(16) 0.0314(15) 0.0022(12) 0.0053(13) 0.0007(14) C12 0.0424(18) 0.0417(18) 0.0329(15) 0.0003(14) 0.0062(14) -0.0024(16) C13 0.081(2) 0.064(2) 0.072(2) 0.0106(19) 0.028(2) 0.012(2) C14 0.078(3) 0.096(3) 0.087(3) 0.044(3) 0.022(2) 0.032(2) C15 0.047(2) 0.0481(19) 0.0491(19) -0.0082(15) 0.0072(17) 0.0059(16) C16 0.095(3) 0.128(3) 0.042(2) 0.005(2) 0.003(2) 0.029(2) O2 0.0414(13) 0.0655(14) 0.0792(15) -0.0231(12) 0.0068(11) -0.0088(11) _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 C15 1.191(3) . ? O3 C12 1.204(3) . ? O4 C15 1.330(3) . ? O4 C16 1.430(3) . ? C1 C2 1.351(5) . ? C1 C14 1.367(5) . ? C1 H1 0.9300 . ? C2 C3 1.363(4) . ? C2 H2 0.9300 . ? C3 C4 1.374(4) . ? C3 H3 0.9300 . ? C4 C13 1.374(4) . ? C4 C5 1.504(4) . ? C5 C6 1.512(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N1 1.454(3) . ? C6 C15 1.513(4) . ? C6 H6 0.9800 . ? N1 C12 1.378(3) . ? N1 C8 1.387(3) . ? C8 O2 1.204(3) . ? C8 C9 1.482(4) . ? C9 C10 1.379(3) 3_756 ? C9 C11 1.381(3) . ? C10 C9 1.379(3) 3_756 ? C10 C11 1.382(3) . ? C10 H10 0.9300 . ? C11 C12 1.488(4) . ? C13 C14 1.402(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 C15 O4 C16 117.1(2) . . ? C2 C1 C14 120.0(3) . . ? C2 C1 H1 120.0 . . ? C14 C1 H1 120.0 . . ? C1 C2 C3 120.1(4) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C4 122.0(3) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C13 C4 C3 118.0(3) . . ? C13 C4 C5 121.4(3) . . ? C3 C4 C5 120.4(3) . . ? C4 C5 C6 109.7(2) . . ? C4 C5 H5A 109.7 . . ? C6 C5 H5A 109.7 . . ? C4 C5 H5B 109.7 . . ? C6 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? N1 C6 C5 111.4(2) . . ? N1 C6 C15 110.8(2) . . ? C5 C6 C15 114.8(2) . . ? N1 C6 H6 106.4 . . ? C5 C6 H6 106.4 . . ? C15 C6 H6 106.4 . . ? C12 N1 C8 112.0(2) . . ? C12 N1 C6 124.8(2) . . ? C8 N1 C6 123.2(2) . . ? O2 C8 N1 125.1(2) . . ? O2 C8 C9 128.6(3) . . ? N1 C8 C9 106.4(2) . . ? C10 C9 C11 122.8(2) 3_756 . ? C10 C9 C8 129.7(2) 3_756 . ? C11 C9 C8 107.5(2) . . ? C9 C10 C11 115.1(2) 3_756 . ? C9 C10 H10 122.4 3_756 . ? C11 C10 H10 122.4 . . ? C9 C11 C10 122.0(2) . . ? C9 C11 C12 108.3(2) . . ? C10 C11 C12 129.7(2) . . ? O3 C12 N1 125.6(2) . . ? O3 C12 C11 128.6(2) . . ? N1 C12 C11 105.8(2) . . ? C4 C13 C14 119.9(3) . . ? C4 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C1 C14 C13 120.0(3) . . ? C1 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? O1 C15 O4 125.2(3) . . ? O1 C15 C6 124.4(3) . . ? O4 C15 C6 110.2(3) . . ? O4 C16 H16A 109.5 . . ? O4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 21.23 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.142 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.034