# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Yingwei Li' _publ_contact_author_address ; School of Chemistry and Chemical Engineering South China University of Technology Guangzhou 510640 P. R. China ; _publ_contact_author_phone '86 20 22236337' _publ_contact_author_fax '86 20 22236337' _publ_contact_author_email liyw@scut.edu.cn _publ_section_title ; A microporous, moisture-stable, and amine-functionalized metal-organic framework for highly selective separation of CO2 from CH4 ; loop_ _publ_author_name 'Bizhen Yuan' 'Deyun Ma' 'Xi Wang' 'Zhong Li' 'Yingwei Li' 'Huimin Liu' 'Dehua He' # Attachment '- 1.cif' data_x _database_code_depnum_ccdc_archive 'CCDC 846041' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H10 In N2 O8' _chemical_formula_sum 'C16 H10 In N2 O8' _chemical_formula_weight 473.08 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' In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'F d d d ' _symmetry_space_group_name_Hall '-F 2uv 2vw ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 15.300(2) _cell_length_b 26.902(4) _cell_length_c 31.342(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 12900(3) _cell_formula_units_Z 16 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5837 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 27.90 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.974 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3728 _exptl_absorpt_coefficient_mu 0.759 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.807 _exptl_absorpt_correction_T_max 0.859 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Bruker APEX-II area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13601 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.20 _reflns_number_total 2896 _reflns_number_gt 2309 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'XP in SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _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^)+(0.0494P)^2^+0.4496P] 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 2896 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0758 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 In1 In 0.3750 0.3750 0.565219(6) 0.01993(10) Uani 1 2 d S . . O2 O 0.26215(10) 0.41156(6) 0.52929(5) 0.0336(4) Uani 1 1 d . . . C7 C 0.31500(17) 0.43852(10) 0.50869(8) 0.0325(6) Uani 1 1 d . . . C1 C 0.28300(17) 0.47183(10) 0.47465(8) 0.0379(7) Uani 1 1 d . . . C2 C 0.33801(19) 0.50530(14) 0.45387(10) 0.0572(10) Uani 1 1 d . . . C6 C 0.19578(18) 0.46959(12) 0.46285(9) 0.0485(8) Uani 1 1 d . . . H6 H 0.1580 0.4471 0.4772 0.058 Uiso 1 1 calc R . . N1 N 0.4246(2) 0.51263(16) 0.46499(13) 0.141(2) Uani 1 1 d . . . H1A H 0.4586 0.5348 0.4477 0.170 Uiso 1 1 d R . . H1B H 0.4526 0.4847 0.4783 0.170 Uiso 1 1 d R . . O1 O 0.39632(11) 0.43589(7) 0.51741(6) 0.0371(4) Uani 1 1 d . . . C5 C 0.1621(2) 0.49922(14) 0.43066(10) 0.0515(9) Uani 1 1 d . . . H5 H 0.1021 0.4973 0.4231 0.062 Uiso 1 1 calc R . . C3 C 0.30388(18) 0.53542(12) 0.42092(10) 0.0500(8) Uani 1 1 d . . . H3 H 0.3409 0.5583 0.4066 0.060 Uiso 1 1 calc R . . C4 C 0.21804(16) 0.53182(10) 0.40960(8) 0.0322(6) Uani 1 1 d . . . C8 C 0.18539(16) 0.56390(9) 0.37403(7) 0.0265(5) Uani 1 1 d . . . O4 O 0.10388(11) 0.56771(7) 0.36719(5) 0.0308(4) Uani 1 1 d . . . O3 O 0.23842(10) 0.58750(6) 0.35101(5) 0.0284(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 In1 0.02296(15) 0.02223(15) 0.01460(14) 0.000 0.000 -0.00095(10) O2 0.0267(9) 0.0419(10) 0.0321(9) 0.0134(8) -0.0053(7) 0.0014(8) C7 0.0331(14) 0.0374(15) 0.0271(13) 0.0091(11) 0.0055(11) -0.0043(12) C1 0.0302(14) 0.0493(17) 0.0342(15) 0.0196(13) -0.0030(11) 0.0011(13) C2 0.0290(15) 0.083(2) 0.060(2) 0.0465(19) -0.0109(14) -0.0119(16) C6 0.0302(15) 0.062(2) 0.0531(19) 0.0340(15) -0.0013(13) -0.0061(14) N1 0.062(2) 0.196(5) 0.167(4) 0.138(4) -0.053(3) -0.057(3) O1 0.0283(10) 0.0500(12) 0.0331(10) 0.0186(9) -0.0014(7) -0.0022(9) C5 0.0291(15) 0.074(2) 0.0517(19) 0.0326(17) -0.0072(13) -0.0006(16) C3 0.0297(15) 0.070(2) 0.0504(18) 0.0381(16) -0.0036(13) -0.0098(14) C4 0.0253(13) 0.0402(15) 0.0311(14) 0.0124(12) 0.0017(11) 0.0028(12) C8 0.0265(13) 0.0279(13) 0.0252(12) 0.0046(11) 0.0085(11) 0.0051(10) O4 0.0242(9) 0.0374(10) 0.0307(10) 0.0098(8) 0.0029(7) 0.0052(8) O3 0.0270(9) 0.0340(9) 0.0242(9) 0.0073(7) -0.0040(7) 0.0040(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 In1 O1 2.2438(17) 2 ? In1 O1 2.2438(17) . ? In1 O4 2.2656(17) 19_666 ? In1 O4 2.2656(17) 32_556 ? In1 O2 2.2840(15) 2 ? In1 O2 2.2840(15) . ? In1 O3 2.2995(15) 19_666 ? In1 O3 2.2995(15) 32_556 ? In1 C7 2.627(2) 2 ? In1 C8 2.637(2) 19_666 ? In1 C8 2.637(2) 32_556 ? O2 C7 1.264(3) . ? C7 O1 1.276(3) . ? C7 C1 1.477(3) . ? C1 C6 1.386(4) . ? C1 C2 1.394(4) . ? C2 N1 1.383(4) . ? C2 C3 1.413(4) . ? C6 C5 1.385(4) . ? C6 H6 0.9500 . ? N1 H1A 0.9602 . ? N1 H1B 0.9601 . ? C5 C4 1.391(4) . ? C5 H5 0.9500 . ? C3 C4 1.364(4) . ? C3 H3 0.9500 . ? C4 C8 1.496(3) . ? C8 O3 1.258(3) . ? C8 O4 1.270(3) . ? C8 In1 2.637(2) 27_565 ? O4 In1 2.2656(17) 27_565 ? O3 In1 2.2995(15) 27_565 ? 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 O1 In1 O1 96.21(10) 2 . ? O1 In1 O4 162.94(6) 2 19_666 ? O1 In1 O4 90.25(8) . 19_666 ? O1 In1 O4 90.25(8) 2 32_556 ? O1 In1 O4 162.94(6) . 32_556 ? O4 In1 O4 88.06(9) 19_666 32_556 ? O1 In1 O2 57.74(6) 2 2 ? O1 In1 O2 82.83(7) . 2 ? O4 In1 O2 139.04(6) 19_666 2 ? O4 In1 O2 87.35(6) 32_556 2 ? O1 In1 O2 82.83(7) 2 . ? O1 In1 O2 57.74(6) . . ? O4 In1 O2 87.35(6) 19_666 . ? O4 In1 O2 139.05(6) 32_556 . ? O2 In1 O2 120.92(9) 2 . ? O1 In1 O3 139.09(6) 2 19_666 ? O1 In1 O3 84.02(6) . 19_666 ? O4 In1 O3 57.21(6) 19_666 19_666 ? O4 In1 O3 80.79(6) 32_556 19_666 ? O2 In1 O3 81.89(6) 2 19_666 ? O2 In1 O3 128.47(6) . 19_666 ? O1 In1 O3 84.02(6) 2 32_556 ? O1 In1 O3 139.09(6) . 32_556 ? O4 In1 O3 80.79(6) 19_666 32_556 ? O4 In1 O3 57.21(6) 32_556 32_556 ? O2 In1 O3 128.47(6) 2 32_556 ? O2 In1 O3 81.89(6) . 32_556 ? O3 In1 O3 121.60(8) 19_666 32_556 ? O1 In1 C7 29.03(7) 2 2 ? O1 In1 C7 88.49(8) . 2 ? O4 In1 C7 167.74(7) 19_666 2 ? O4 In1 C7 89.58(7) 32_556 2 ? O2 In1 C7 28.75(7) 2 2 ? O2 In1 C7 102.22(7) . 2 ? O3 In1 C7 110.53(7) 19_666 2 ? O3 In1 C7 107.90(7) 32_556 2 ? O1 In1 C8 166.61(7) 2 19_666 ? O1 In1 C8 87.75(7) . 19_666 ? O4 In1 C8 28.76(7) 19_666 19_666 ? O4 In1 C8 82.62(7) 32_556 19_666 ? O2 In1 C8 110.38(6) 2 19_666 ? O2 In1 C8 109.95(7) . 19_666 ? O3 In1 C8 28.48(6) 19_666 19_666 ? O3 In1 C8 101.35(6) 32_556 19_666 ? C7 In1 C8 138.98(8) 2 19_666 ? O1 In1 C8 87.75(7) 2 32_556 ? O1 In1 C8 166.61(7) . 32_556 ? O4 In1 C8 82.62(7) 19_666 32_556 ? O4 In1 C8 28.76(7) 32_556 32_556 ? O2 In1 C8 109.95(7) 2 32_556 ? O2 In1 C8 110.38(6) . 32_556 ? O3 In1 C8 101.35(6) 19_666 32_556 ? O3 In1 C8 28.48(6) 32_556 32_556 ? C7 In1 C8 100.86(8) 2 32_556 ? C8 In1 C8 91.30(10) 19_666 32_556 ? C7 O2 In1 90.88(14) . . ? O2 C7 O1 118.9(2) . . ? O2 C7 C1 120.4(2) . . ? O1 C7 C1 120.8(2) . . ? C6 C1 C2 119.0(2) . . ? C6 C1 C7 119.0(2) . . ? C2 C1 C7 122.0(2) . . ? N1 C2 C1 123.5(3) . . ? N1 C2 C3 117.1(3) . . ? C1 C2 C3 119.3(3) . . ? C5 C6 C1 121.8(3) . . ? C5 C6 H6 119.1 . . ? C1 C6 H6 119.1 . . ? C2 N1 H1A 117.8 . . ? C2 N1 H1B 115.2 . . ? H1A N1 H1B 119.3 . . ? C7 O1 In1 92.40(14) . . ? C6 C5 C4 118.7(3) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.9(2) . . ? C3 C4 C8 118.3(2) . . ? C5 C4 C8 120.8(2) . . ? O3 C8 O4 119.7(2) . . ? O3 C8 C4 120.2(2) . . ? O4 C8 C4 120.0(2) . . ? O3 C8 In1 60.69(11) . 27_565 ? O4 C8 In1 59.17(12) . 27_565 ? C4 C8 In1 176.12(18) . 27_565 ? C8 O4 In1 92.07(14) . 27_565 ? C8 O3 In1 90.83(14) . 27_565 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.527 _refine_diff_density_min -0.639 _refine_diff_density_rms 0.069 _iucr_refine_instruction_details ; TITL 1 in Fddd CELL 0.71073 15.3000 26.9020 31.3421 90.000 90.000 90.000 ZERR 16.00 0.0022 0.0039 0.0045 0.000 0.000 0.000 LATT 4 SYMM 0.75-X, 0.75-Y, Z SYMM 0.75-X, Y, 0.75-Z SYMM X, 0.75-Y, 0.75-Z SFAC C H N O In UNIT 256 160 32 128 16 omit 0 4 0 omit 1 1 5 omit 1 1 1 omit 0 0 4 omit 3 3 3 omit 0 4 8 omit 1 3 7 omit 0 2 2 omit 2 4 4 OMIT -3 50.4 L.S. 20 ACTA BOND $h FMAP 2 PLAN 40 size 0.30 0.28 0.22 FREE C7 In1 DFIX 2.50 0.01 C10 C11 C10 C12 DFIX 2.6 0.01 C11 C12 DFIX 1.45 0.01 N3 C11 N3 C12 N3 C10 DFIX 1.30 0.01 C10 O5 WGHT 0.049400 0.449590 FVAR 0.743050 0.449590 TEMP -163 MOLE 1 In1 5 0.375000 0.375000 0.565219 10.500000 0.022960 = 0.022230 0.014600 0.000000 0.000000 -0.000950 O2 4 0.262151 0.411556 0.529289 11.000000 0.026740 = 0.041890 0.032130 0.013410 -0.005250 0.001430 C7 1 0.314997 0.438521 0.508688 11.000000 0.033090 = 0.037400 0.027060 0.009150 0.005540 -0.004270 C1 1 0.283001 0.471834 0.474652 11.000000 0.030230 = 0.049310 0.034170 0.019570 -0.003020 0.001070 C2 1 0.338013 0.505303 0.453873 11.000000 0.028960 = 0.082560 0.060180 0.046530 -0.010870 -0.011930 C6 1 0.195784 0.469590 0.462852 11.000000 0.030230 = 0.062110 0.053060 0.033970 -0.001320 -0.006070 AFIX 43 H6 2 0.158041 0.447113 0.477241 11.000000 -1.200000 AFIX 0 N1 3 0.424562 0.512635 0.464987 11.000000 0.062200 = 0.195540 0.166740 0.138180 -0.052590 -0.057330 AFIX 3 H1A 2 0.458622 0.534815 0.447676 11.000000 -1.200000 H1B 2 0.452602 0.484725 0.478297 11.000000 -1.200000 AFIX 0 O1 4 0.396319 0.435889 0.517412 11.000000 0.028270 = 0.049960 0.033140 0.018630 -0.001410 -0.002230 C5 1 0.162145 0.499221 0.430657 11.000000 0.029080 = 0.073710 0.051650 0.032640 -0.007170 -0.000550 AFIX 43 H5 2 0.102107 0.497323 0.423100 11.000000 -1.200000 AFIX 0 C3 1 0.303878 0.535420 0.420918 11.000000 0.029670 = 0.069800 0.050400 0.038060 -0.003620 -0.009760 AFIX 43 H3 2 0.340919 0.558300 0.406562 11.000000 -1.200000 AFIX 0 C4 1 0.218043 0.531823 0.409604 11.000000 0.025320 = 0.040180 0.031110 0.012380 0.001690 0.002820 C8 1 0.185389 0.563899 0.374029 11.000000 0.026530 = 0.027890 0.025210 0.004590 0.008480 0.005090 O4 4 0.103879 0.567712 0.367193 11.000000 0.024160 = 0.037420 0.030730 0.009840 0.002940 0.005230 O3 4 0.238420 0.587502 0.351015 11.000000 0.027010 = 0.033980 0.024200 0.007260 -0.003950 0.004050 HKLF 4 REM 1 in Fddd REM R1= 0.0278 for 2309 Fo > 4sig(Fo) and 0.0342 for all 2896 data REM 124 parameters refined using 0 restraints END ; # SQUEEZE RESULTS (APPEND TO CIF) 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 1 -0.004 -0.018 -0.005 3116.1 689.4 2 0.625 0.125 0.125 169.4 22.7 3 0.125 0.125 0.625 169.4 22.7 4 0.375 0.375 0.375 169.4 23.1 5 0.875 0.375 0.875 169.4 23.1 6 0.125 0.625 0.125 169.4 22.7 7 0.625 0.625 0.625 169.4 22.7 8 0.875 0.875 0.375 169.4 23.1 9 0.375 0.875 0.875 169.4 23.1 _platon_squeeze_details ; ; #==END