# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Qi-Yu Zheng' _publ_contact_author_email ZHENGQY@ICCAS.AC.CN _publ_section_title ; Organic hydrogen-bonded interpenetrating diamondoid frameworks from modular self-assembly of methanetetrabenzoic acid with linkers ; loop_ _publ_author_name 'Qi-Yu Zheng' 'Zhi-Tang Huang' 'Yong-Biao Men' 'Junliang Sun' # Attachment 'HMTBphen_708658_-revised.cif' data_myb1 _database_code_depnum_ccdc_archive 'CCDC 708658' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H20 O8, C12 H8 N2' _chemical_formula_sum 'C41 H28 N2 O8' _chemical_formula_weight 676.65 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 C2/c loop_ _symmetry_equiv_pos_as_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 25.574(5) _cell_length_b 8.6352(17) _cell_length_c 17.905(4) _cell_angle_alpha 90.00 _cell_angle_beta 122.61(3) _cell_angle_gamma 90.00 _cell_volume 3330.5(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 786 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9604 _exptl_absorpt_correction_T_max 0.9767 _exptl_absorpt_process_details 'ABSCOR by T.Higashi 8 March, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku raxis Rapid IP Area Detector' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5209 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2931 _reflns_number_gt 2373 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (Sheldrick, 1997)' _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^)+(0.0560P)^2^+0.7938P] 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 2931 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1256 _refine_ls_wR_factor_gt 0.1162 _refine_ls_goodness_of_fit_ref 1.189 _refine_ls_restrained_S_all 1.189 _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 -0.04655(8) 1.84400(19) -0.02322(11) 0.0377(5) Uani 1 1 d . . . O2 O 0.05527(8) 1.8688(2) 0.07501(12) 0.0396(5) Uani 1 1 d . . . H2A H 0.0483 1.9596 0.0550 0.059 Uiso 1 1 calc R . . O3 O 0.20169(8) 0.74433(19) 0.33975(11) 0.0335(4) Uani 1 1 d . . . O4 O 0.17781(7) 0.69688(19) 0.44047(10) 0.0300(4) Uani 1 1 d . . . H4 H 0.2005 0.6191 0.4509 0.045 Uiso 1 1 calc R . . N1 N 0.23202(8) 0.4063(2) 0.47749(12) 0.0232(4) Uani 1 1 d . . . C1 C 0.0000 1.2886(3) 0.2500 0.0170(6) Uani 1 2 d S . . C2 C 0.00251(9) 1.4020(2) 0.18538(14) 0.0191(5) Uani 1 1 d . . . C3 C -0.04958(10) 1.4411(3) 0.10396(15) 0.0238(5) Uani 1 1 d . . . H3A H -0.0865 1.3821 0.0809 0.029 Uiso 1 1 calc R . . C4 C -0.04848(10) 1.5654(3) 0.05578(15) 0.0255(5) Uani 1 1 d . . . H4A H -0.0847 1.5913 0.0004 0.031 Uiso 1 1 calc R . . C5 C 0.00499(10) 1.6519(2) 0.08779(15) 0.0220(5) Uani 1 1 d . . . C6 C 0.05852(10) 1.6096(3) 0.16775(15) 0.0244(5) Uani 1 1 d . . . H6A H 0.0960 1.6657 0.1892 0.029 Uiso 1 1 calc R . . C7 C 0.05715(10) 1.4866(2) 0.21559(15) 0.0221(5) Uani 1 1 d . . . H7A H 0.0939 1.4586 0.2700 0.027 Uiso 1 1 calc R . . C9 C 0.00401(10) 1.7961(3) 0.04233(15) 0.0242(5) Uani 1 1 d . . . C10 C 0.05512(10) 1.1747(2) 0.29415(14) 0.0189(5) Uani 1 1 d . . . C11 C 0.08625(10) 1.1351(2) 0.25254(15) 0.0220(5) Uani 1 1 d . . . H11A H 0.0799 1.1946 0.2037 0.026 Uiso 1 1 calc R . . C12 C 0.12628(10) 1.0099(3) 0.28197(15) 0.0233(5) Uani 1 1 d . . . H12A H 0.1470 0.9836 0.2528 0.028 Uiso 1 1 calc R . . C13 C 0.13656(10) 0.9223(2) 0.35348(14) 0.0202(5) Uani 1 1 d . . . C14 C 0.10750(10) 0.9640(3) 0.39757(14) 0.0219(5) Uani 1 1 d . . . H14A H 0.1152 0.9068 0.4478 0.026 Uiso 1 1 calc R . . C15 C 0.06747(10) 1.0890(2) 0.36793(15) 0.0229(5) Uani 1 1 d . . . H15A H 0.0479 1.1171 0.3985 0.027 Uiso 1 1 calc R . . C16 C 0.17575(10) 0.7806(3) 0.37727(14) 0.0217(5) Uani 1 1 d . . . C17 C 0.27427(12) 0.3060(3) 0.32001(18) 0.0370(6) Uani 1 1 d . . . H17A H 0.2759 0.3527 0.2733 0.044 Uiso 1 1 calc R . . C18 C 0.25507(12) 0.3906(3) 0.36468(17) 0.0346(6) Uani 1 1 d . . . H18A H 0.2437 0.4960 0.3495 0.041 Uiso 1 1 calc R . . C19 C 0.25190(10) 0.3219(3) 0.43413(15) 0.0225(5) Uani 1 1 d . . . C20 C 0.23021(9) 0.3365(3) 0.54333(14) 0.0199(5) Uani 1 1 d . . . C21 C 0.21065(10) 0.4210(3) 0.59210(15) 0.0246(5) Uani 1 1 d . . . H21A H 0.1993 0.5268 0.5786 0.030 Uiso 1 1 calc R . . C22 C 0.20809(11) 0.3511(3) 0.65788(16) 0.0288(6) Uani 1 1 d . . . H22A H 0.1943 0.4081 0.6895 0.035 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 0.0420(11) 0.0316(10) 0.0326(10) 0.0113(8) 0.0156(9) -0.0008(8) O2 0.0435(11) 0.0262(10) 0.0458(12) 0.0098(8) 0.0218(9) -0.0091(8) O3 0.0423(10) 0.0302(10) 0.0401(10) 0.0112(8) 0.0301(9) 0.0142(8) O4 0.0380(10) 0.0240(9) 0.0348(10) 0.0127(7) 0.0241(8) 0.0143(7) N1 0.0249(10) 0.0202(10) 0.0262(11) 0.0036(8) 0.0148(9) 0.0045(8) C1 0.0193(15) 0.0131(15) 0.0174(15) 0.000 0.0090(13) 0.000 C2 0.0224(12) 0.0140(11) 0.0217(12) -0.0011(9) 0.0123(10) 0.0020(8) C3 0.0215(12) 0.0204(12) 0.0251(13) 0.0008(10) 0.0096(10) -0.0042(9) C4 0.0269(12) 0.0206(12) 0.0227(12) 0.0039(10) 0.0093(11) -0.0001(10) C5 0.0294(12) 0.0160(12) 0.0247(12) -0.0001(9) 0.0172(11) -0.0020(9) C6 0.0257(12) 0.0183(12) 0.0312(14) -0.0011(10) 0.0168(11) -0.0027(10) C7 0.0202(12) 0.0171(12) 0.0246(12) 0.0034(9) 0.0091(10) 0.0021(9) C9 0.0272(12) 0.0202(12) 0.0242(13) -0.0016(10) 0.0132(11) -0.0031(10) C10 0.0235(11) 0.0123(11) 0.0213(12) -0.0038(9) 0.0124(10) -0.0024(9) C11 0.0269(12) 0.0196(12) 0.0207(12) 0.0043(10) 0.0136(10) 0.0013(9) C12 0.0262(12) 0.0208(12) 0.0253(12) 0.0013(10) 0.0154(11) 0.0022(9) C13 0.0202(11) 0.0177(12) 0.0206(12) -0.0007(9) 0.0097(10) 0.0003(9) C14 0.0284(12) 0.0179(12) 0.0199(12) 0.0047(9) 0.0134(10) 0.0022(9) C15 0.0297(12) 0.0191(12) 0.0248(13) -0.0006(9) 0.0180(11) 0.0034(9) C16 0.0222(11) 0.0184(12) 0.0223(12) 0.0013(10) 0.0104(10) -0.0011(9) C17 0.0529(16) 0.0364(15) 0.0393(15) 0.0097(12) 0.0364(14) 0.0083(13) C18 0.0525(16) 0.0265(14) 0.0378(15) 0.0110(11) 0.0330(14) 0.0106(12) C19 0.0239(12) 0.0205(12) 0.0243(12) 0.0012(10) 0.0136(10) 0.0022(9) C20 0.0195(11) 0.0202(12) 0.0193(11) 0.0006(9) 0.0101(10) -0.0011(9) C21 0.0255(12) 0.0231(12) 0.0279(13) 0.0005(10) 0.0161(11) 0.0050(9) C22 0.0332(13) 0.0296(14) 0.0320(14) -0.0016(11) 0.0232(12) 0.0044(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 C9 1.259(3) . ? O2 C9 1.276(3) . ? O2 H2A 0.8400 . ? O3 C16 1.212(3) . ? O4 C16 1.319(3) . ? O4 H4 0.8400 . ? N1 C20 1.347(3) . ? N1 C19 1.348(3) . ? C1 C10 1.542(3) 2 ? C1 C10 1.542(3) . ? C1 C2 1.543(3) 2 ? C1 C2 1.543(3) . ? C2 C3 1.386(3) . ? C2 C7 1.402(3) . ? C3 C4 1.386(3) . ? C3 H3A 0.9500 . ? C4 C5 1.382(3) . ? C4 H4A 0.9500 . ? C5 C6 1.394(3) . ? C5 C9 1.481(3) . ? C6 C7 1.377(3) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C10 C15 1.394(3) . ? C10 C11 1.395(3) . ? C11 C12 1.383(3) . ? C11 H11A 0.9500 . ? C12 C13 1.385(3) . ? C12 H12A 0.9500 . ? C13 C14 1.392(3) . ? C13 C16 1.491(3) . ? C14 C15 1.381(3) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C17 C18 1.355(3) . ? C17 C22 1.417(3) 7_556 ? C17 H17A 0.9500 . ? C18 C19 1.419(3) . ? C18 H18A 0.9500 . ? C19 C20 1.429(3) 7_556 ? C20 C21 1.420(3) . ? C20 C19 1.429(3) 7_556 ? C21 C22 1.356(3) . ? C21 H21A 0.9500 . ? C22 C17 1.417(3) 7_556 ? C22 H22A 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 C9 O2 H2A 109.5 . . ? C16 O4 H4 109.5 . . ? C20 N1 C19 117.59(19) . . ? C10 C1 C10 100.7(2) 2 . ? C10 C1 C2 113.16(11) 2 2 ? C10 C1 C2 114.60(11) . 2 ? C10 C1 C2 114.60(11) 2 . ? C10 C1 C2 113.16(11) . . ? C2 C1 C2 101.2(2) 2 . ? C3 C2 C7 118.2(2) . . ? C3 C2 C1 122.60(17) . . ? C7 C2 C1 118.49(17) . . ? C2 C3 C4 120.9(2) . . ? C2 C3 H3A 119.6 . . ? C4 C3 H3A 119.6 . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? C4 C5 C6 119.3(2) . . ? C4 C5 C9 120.4(2) . . ? C6 C5 C9 120.0(2) . . ? C7 C6 C5 120.0(2) . . ? C7 C6 H6A 120.0 . . ? C5 C6 H6A 120.0 . . ? C6 C7 C2 121.1(2) . . ? C6 C7 H7A 119.5 . . ? C2 C7 H7A 119.5 . . ? O1 C9 O2 123.4(2) . . ? O1 C9 C5 119.6(2) . . ? O2 C9 C5 116.9(2) . . ? C15 C10 C11 118.2(2) . . ? C15 C10 C1 120.15(17) . . ? C11 C10 C1 120.64(17) . . ? C12 C11 C10 120.4(2) . . ? C12 C11 H11A 119.8 . . ? C10 C11 H11A 119.8 . . ? C11 C12 C13 120.8(2) . . ? C11 C12 H12A 119.6 . . ? C13 C12 H12A 119.6 . . ? C12 C13 C14 119.3(2) . . ? C12 C13 C16 118.41(19) . . ? C14 C13 C16 122.2(2) . . ? C15 C14 C13 119.7(2) . . ? C15 C14 H14A 120.1 . . ? C13 C14 H14A 120.1 . . ? C14 C15 C10 121.4(2) . . ? C14 C15 H15A 119.3 . . ? C10 C15 H15A 119.3 . . ? O3 C16 O4 123.6(2) . . ? O3 C16 C13 122.5(2) . . ? O4 C16 C13 113.85(19) . . ? C18 C17 C22 120.9(2) . 7_556 ? C18 C17 H17A 119.6 . . ? C22 C17 H17A 119.6 7_556 . ? C17 C18 C19 120.1(2) . . ? C17 C18 H18A 119.9 . . ? C19 C18 H18A 119.9 . . ? N1 C19 C18 119.7(2) . . ? N1 C19 C20 121.2(2) . 7_556 ? C18 C19 C20 119.1(2) . 7_556 ? N1 C20 C21 119.8(2) . . ? N1 C20 C19 121.25(19) . 7_556 ? C21 C20 C19 118.9(2) . 7_556 ? C22 C21 C20 120.2(2) . . ? C22 C21 H21A 119.9 . . ? C20 C21 H21A 119.9 . . ? C21 C22 C17 120.8(2) . 7_556 ? C21 C22 H22A 119.6 . . ? C17 C22 H22A 119.6 7_556 . ? 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 C10 C1 C2 C3 23.5(3) 2 . . . ? C10 C1 C2 C3 138.2(2) . . . . ? C2 C1 C2 C3 -98.6(2) 2 . . . ? C10 C1 C2 C7 -166.63(18) 2 . . . ? C10 C1 C2 C7 -51.9(3) . . . . ? C2 C1 C2 C7 71.23(17) 2 . . . ? C7 C2 C3 C4 -3.1(3) . . . . ? C1 C2 C3 C4 166.8(2) . . . . ? C2 C3 C4 C5 0.7(3) . . . . ? C3 C4 C5 C6 2.2(3) . . . . ? C3 C4 C5 C9 -172.1(2) . . . . ? C4 C5 C6 C7 -2.5(3) . . . . ? C9 C5 C6 C7 171.8(2) . . . . ? C5 C6 C7 C2 0.0(3) . . . . ? C3 C2 C7 C6 2.8(3) . . . . ? C1 C2 C7 C6 -167.5(2) . . . . ? C4 C5 C9 O1 3.6(3) . . . . ? C6 C5 C9 O1 -170.7(2) . . . . ? C4 C5 C9 O2 -179.2(2) . . . . ? C6 C5 C9 O2 6.6(3) . . . . ? C10 C1 C10 C15 -71.57(18) 2 . . . ? C2 C1 C10 C15 50.2(3) 2 . . . ? C2 C1 C10 C15 165.63(18) . . . . ? C10 C1 C10 C11 97.0(2) 2 . . . ? C2 C1 C10 C11 -141.24(19) 2 . . . ? C2 C1 C10 C11 -25.8(3) . . . . ? C15 C10 C11 C12 2.7(3) . . . . ? C1 C10 C11 C12 -166.1(2) . . . . ? C10 C11 C12 C13 -0.5(3) . . . . ? C11 C12 C13 C14 -1.8(3) . . . . ? C11 C12 C13 C16 174.7(2) . . . . ? C12 C13 C14 C15 1.9(3) . . . . ? C16 C13 C14 C15 -174.4(2) . . . . ? C13 C14 C15 C10 0.3(3) . . . . ? C11 C10 C15 C14 -2.6(3) . . . . ? C1 C10 C15 C14 166.2(2) . . . . ? C12 C13 C16 O3 4.3(3) . . . . ? C14 C13 C16 O3 -179.2(2) . . . . ? C12 C13 C16 O4 -173.66(19) . . . . ? C14 C13 C16 O4 2.8(3) . . . . ? C22 C17 C18 C19 -0.5(4) 7_556 . . . ? C20 N1 C19 C18 -179.6(2) . . . . ? C20 N1 C19 C20 0.6(3) . . . 7_556 ? C17 C18 C19 N1 -179.2(2) . . . . ? C17 C18 C19 C20 0.6(4) . . . 7_556 ? C19 N1 C20 C21 178.9(2) . . . . ? C19 N1 C20 C19 -0.6(3) . . . 7_556 ? N1 C20 C21 C22 179.3(2) . . . . ? C19 C20 C21 C22 -1.1(3) 7_556 . . . ? C20 C21 C22 C17 1.0(3) . . . 7_556 ? 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 O2 H2A O1 0.84 1.78 2.614(2) 170.8 5_595 O4 H4 N1 0.84 1.96 2.769(2) 161.6 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.221 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.051 # Attachment 'HMTBbipy_708659_-revised.cif' data_myb2 _database_code_depnum_ccdc_archive 'CCDC 708659' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H20 O8, 2 C10 H8 N2' _chemical_formula_sum 'C49 H36 N4 O8' _chemical_formula_weight 808.82 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 Tetragonal _symmetry_space_group_name_H-M I4(1)/acd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+1/4, x+3/4, z+1/4' 'y+1/4, -x+1/4, z+3/4' '-x+1/2, y, -z' 'x, -y, -z+1/2' 'y+1/4, x+3/4, -z+3/4' '-y+1/4, -x+1/4, -z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+3/4, x+5/4, z+3/4' 'y+3/4, -x+3/4, z+5/4' '-x+1, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1' 'y+3/4, x+5/4, -z+5/4' '-y+3/4, -x+3/4, -z+3/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-1/4, -x-3/4, -z-1/4' '-y-1/4, x-1/4, -z-3/4' 'x-1/2, -y, z' '-x, y, z-1/2' '-y-1/4, -x-3/4, z-3/4' 'y-1/4, x-1/4, z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y+1/4, -x-1/4, -z+1/4' '-y+1/4, x+1/4, -z-1/4' 'x, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' '-y+1/4, -x-1/4, z-1/4' 'y+1/4, x+1/4, z+1/4' _cell_length_a 12.7276(18) _cell_length_b 12.7276(18) _cell_length_c 56.994(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9233(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1523 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.48 _exptl_crystal_description colorless _exptl_crystal_colour plate _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3376 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9610 _exptl_absorpt_correction_T_max 0.9849 _exptl_absorpt_process_details 'ABSCOR by T.Higashi 8 March, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku raxis Rapid IP Area Detector' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3944 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0629 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -67 _diffrn_reflns_limit_l_max 61 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2046 _reflns_number_gt 1290 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (Sheldrick, 1997)' _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^)+(0.0480P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2046 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0800 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 0.893 _refine_ls_restrained_S_all 0.893 _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 O2 O 0.13954(11) 0.47989(10) 0.06256(2) 0.0504(4) Uani 1 1 d . . . H2A H 0.0920 0.4925 0.0527 0.076 Uiso 1 1 calc R . . O1 O 0.13938(12) 0.32252(11) 0.04519(2) 0.0529(4) Uani 1 1 d . . . C2 C 0.41269(14) 0.28995(13) 0.10838(3) 0.0274(4) Uani 1 1 d . . . C1 C 0.5000 0.2500 0.1250 0.0267(8) Uani 1 4 d S . . C5 C 0.25873(15) 0.35345(14) 0.07635(3) 0.0322(5) Uani 1 1 d . . . C7 C 0.37365(14) 0.22085(13) 0.09142(3) 0.0310(5) Uani 1 1 d . . . H7A H 0.4007 0.1514 0.0906 0.037 Uiso 1 1 calc R . . C4 C 0.29828(15) 0.42331(15) 0.09266(3) 0.0363(5) Uani 1 1 d . . . H4A H 0.2729 0.4935 0.0930 0.044 Uiso 1 1 calc R . . C6 C 0.29728(14) 0.25125(16) 0.07591(3) 0.0318(4) Uani 1 1 d . . . H6A H 0.2706 0.2024 0.0648 0.038 Uiso 1 1 calc R . . C8 C 0.17370(15) 0.38286(16) 0.05968(4) 0.0389(5) Uani 1 1 d . . . C3 C 0.37471(15) 0.39208(14) 0.10856(3) 0.0326(5) Uani 1 1 d . . . H3A H 0.4013 0.4411 0.1197 0.039 Uiso 1 1 calc R . . N1 N 0.02598(13) -0.00851(15) 0.03638(3) 0.0481(5) Uani 1 1 d . . . C12 C 0.17556(16) 0.07841(17) 0.02045(3) 0.0421(5) Uani 1 1 d . . . H12A H 0.2172 0.1402 0.0196 0.050 Uiso 1 1 calc R . . C13 C 0.08760(17) 0.07596(17) 0.03435(4) 0.0482(6) Uani 1 1 d . . . H13A H 0.0696 0.1373 0.0430 0.058 Uiso 1 1 calc R . . C11 C 0.20303(14) -0.01000(16) 0.00770(3) 0.0373(5) Uani 1 1 d . . . C10 C 0.13925(17) -0.09819(17) 0.00983(4) 0.0503(6) Uani 1 1 d . . . H10A H 0.1551 -0.1608 0.0015 0.060 Uiso 1 1 calc R . . C9 C 0.05271(18) -0.09294(17) 0.02424(4) 0.0526(6) Uani 1 1 d . . . H9A H 0.0096 -0.1536 0.0256 0.063 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 O2 0.0546(10) 0.0364(9) 0.0603(9) -0.0058(7) -0.0295(8) 0.0110(7) O1 0.0620(10) 0.0410(9) 0.0556(9) -0.0090(8) -0.0323(8) 0.0061(7) C2 0.0273(11) 0.0271(11) 0.0278(9) -0.0001(8) 0.0011(8) -0.0005(8) C1 0.0254(11) 0.0254(11) 0.0291(18) 0.000 0.000 0.000 C5 0.0348(11) 0.0302(11) 0.0315(9) 0.0011(9) -0.0055(10) 0.0010(9) C7 0.0368(12) 0.0226(10) 0.0336(11) -0.0004(8) -0.0030(9) 0.0025(8) C4 0.0372(11) 0.0280(11) 0.0436(11) -0.0037(9) -0.0075(10) 0.0053(9) C6 0.0375(11) 0.0274(10) 0.0306(8) -0.0059(10) -0.0045(9) -0.0020(10) C8 0.0436(13) 0.0319(12) 0.0413(11) 0.0015(10) -0.0074(10) 0.0015(10) C3 0.0346(11) 0.0270(11) 0.0363(11) -0.0042(9) -0.0058(9) 0.0000(9) N1 0.0483(12) 0.0373(11) 0.0586(10) 0.0016(10) 0.0184(9) 0.0054(9) C12 0.0384(13) 0.0398(13) 0.0481(12) -0.0060(11) 0.0065(11) -0.0021(9) C13 0.0478(14) 0.0443(14) 0.0524(14) -0.0086(11) 0.0103(12) 0.0035(11) C11 0.0388(11) 0.0367(11) 0.0364(11) 0.0012(10) 0.0053(9) 0.0013(10) C10 0.0534(14) 0.0359(13) 0.0615(14) -0.0053(11) 0.0227(12) -0.0005(10) C9 0.0538(15) 0.0337(13) 0.0704(16) -0.0010(12) 0.0259(12) -0.0014(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 O2 C8 1.320(2) . ? O2 H2A 0.8400 . ? O1 C8 1.209(2) . ? C2 C3 1.387(2) . ? C2 C7 1.398(2) . ? C2 C1 1.5461(18) . ? C1 C2 1.5461(18) 27_565 ? C1 C2 1.5461(18) 20_656 ? C1 C2 1.5461(18) 10_554 ? C5 C4 1.381(2) . ? C5 C6 1.390(3) . ? C5 C8 1.488(3) . ? C7 C6 1.370(2) . ? C7 H7A 0.9500 . ? C4 C3 1.387(2) . ? C4 H4A 0.9500 . ? C6 H6A 0.9500 . ? C3 H3A 0.9500 . ? N1 C9 1.323(3) . ? N1 C13 1.336(3) . ? C12 C13 1.372(3) . ? C12 C11 1.384(3) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C11 C10 1.391(3) . ? C11 C11 1.484(3) 5 ? C10 C9 1.376(3) . ? C10 H10A 0.9500 . ? C9 H9A 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 C8 O2 H2A 109.5 . . ? C3 C2 C7 118.07(16) . . ? C3 C2 C1 123.67(14) . . ? C7 C2 C1 118.17(13) . . ? C2 C1 C2 112.04(7) 27_565 . ? C2 C1 C2 104.44(13) 27_565 20_656 ? C2 C1 C2 112.04(7) . 20_656 ? C2 C1 C2 112.04(7) 27_565 10_554 ? C2 C1 C2 104.44(13) . 10_554 ? C2 C1 C2 112.04(7) 20_656 10_554 ? C4 C5 C6 119.07(17) . . ? C4 C5 C8 122.20(17) . . ? C6 C5 C8 118.70(16) . . ? C6 C7 C2 121.38(16) . . ? C6 C7 H7A 119.3 . . ? C2 C7 H7A 119.3 . . ? C5 C4 C3 120.69(17) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C7 C6 C5 120.20(17) . . ? C7 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? O1 C8 O2 124.08(18) . . ? O1 C8 C5 122.62(18) . . ? O2 C8 C5 113.30(17) . . ? C2 C3 C4 120.55(17) . . ? C2 C3 H3A 119.7 . . ? C4 C3 H3A 119.7 . . ? C9 N1 C13 117.23(18) . . ? C13 C12 C11 119.4(2) . . ? C13 C12 H12A 120.3 . . ? C11 C12 H12A 120.3 . . ? N1 C13 C12 123.2(2) . . ? N1 C13 H13A 118.4 . . ? C12 C13 H13A 118.4 . . ? C12 C11 C10 117.59(17) . . ? C12 C11 C11 120.94(13) . 5 ? C10 C11 C11 121.47(13) . 5 ? C9 C10 C11 118.7(2) . . ? C9 C10 H10A 120.7 . . ? C11 C10 H10A 120.7 . . ? N1 C9 C10 123.9(2) . . ? N1 C9 H9A 118.0 . . ? C10 C9 H9A 118.0 . . ? 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 C3 C2 C1 C2 -0.32(17) . . . 27_565 ? C7 C2 C1 C2 176.23(15) . . . 27_565 ? C3 C2 C1 C2 116.7(2) . . . 20_656 ? C7 C2 C1 C2 -66.75(10) . . . 20_656 ? C3 C2 C1 C2 -121.82(19) . . . 10_554 ? C7 C2 C1 C2 54.74(12) . . . 10_554 ? C3 C2 C7 C6 -2.4(3) . . . . ? C1 C2 C7 C6 -179.16(14) . . . . ? C6 C5 C4 C3 -0.6(3) . . . . ? C8 C5 C4 C3 177.47(18) . . . . ? C2 C7 C6 C5 1.8(3) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C8 C5 C6 C7 -178.35(17) . . . . ? C4 C5 C8 O1 179.21(19) . . . . ? C6 C5 C8 O1 -2.7(3) . . . . ? C4 C5 C8 O2 -1.5(3) . . . . ? C6 C5 C8 O2 176.53(17) . . . . ? C7 C2 C3 C4 1.6(3) . . . . ? C1 C2 C3 C4 178.13(14) . . . . ? C5 C4 C3 C2 -0.1(3) . . . . ? C9 N1 C13 C12 0.1(3) . . . . ? C11 C12 C13 N1 0.2(3) . . . . ? C13 C12 C11 C10 -0.4(3) . . . . ? C13 C12 C11 C11 179.4(2) . . . 5 ? C12 C11 C10 C9 0.3(3) . . . . ? C11 C11 C10 C9 -179.4(2) 5 . . . ? C13 N1 C9 C10 -0.1(3) . . . . ? C11 C10 C9 N1 -0.1(3) . . . . ? 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 O2 H2A N1 0.84 1.78 2.607(2) 168.3 10_454 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.189 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.035 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.250 0.125 183 44 ' ' 2 0.000 0.750 0.375 183 44 ' ' 3 0.000 0.250 0.625 183 44 ' ' 4 0.000 0.750 0.875 183 44 ' ' 5 0.500 0.750 0.125 183 44 ' ' 6 0.500 0.250 0.375 183 44 ' ' 7 0.500 0.750 0.625 183 44 ' ' 8 0.500 0.250 0.875 183 44 ' ' _platon_squeeze_details ; ;