# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Iris Oppel' 'Rudiger Seidel' _publ_contact_author_name 'Iris Oppel' _publ_contact_author_email IRIS.OPPEL@RUB.DE _publ_section_title ; Assembly of a rhomboidally distorted (4,4)-net based polymeric sheet structure bearing copper(II) 5,10,15,20-tetra(4-pyridyl)porphyrin ; # Attachment 'rs580cu.cif' data_rs580cu _database_code_depnum_ccdc_archive 'CCDC 751857' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C60 H28 Cu3 F24 N8 O8, 6 H2O' _chemical_formula_sum 'C60 H40 Cu3 F24 N8 O14' _chemical_formula_weight 1743.62 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' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/m' _symmetry_space_group_name_Hall '-C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 22.8333(6) _cell_length_b 25.7253(6) _cell_length_c 6.42264(16) _cell_angle_alpha 90.00 _cell_angle_beta 105.895(3) _cell_angle_gamma 90.00 _cell_volume 3628.38(17) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 3129 _cell_measurement_theta_min 3.4368 _cell_measurement_theta_max 65.3999 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1742 _exptl_absorpt_coefficient_mu 2.173 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5523 _exptl_absorpt_correction_T_max 0.8284 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur^TM^2, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.4171 _diffrn_reflns_number 10029 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 65.55 _reflns_number_total 3155 _reflns_number_gt 2259 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond 3.2c (Brandenburg, 2009)' _computing_publication_material 'enCIFer 1.3 (Allen et al., 2004)' _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^)+(0.0607P)^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 3155 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 0.902 _refine_ls_restrained_S_all 0.902 _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 Cu1 Cu 0.5000 0.5000 0.5000 0.0162(2) Uani 1 4 d S . . N21 N 0.43868(15) 0.5000 0.6703(6) 0.0214(7) Uani 1 2 d S . . N22 N 0.5000 0.42264(12) 0.5000 0.0165(7) Uani 1 2 d S . . C3 C 0.36790(15) 0.47393(12) 0.8460(6) 0.0358(8) Uani 1 1 d . . . H3 H 0.3435 0.4520 0.9072 0.043 Uiso 1 1 calc R . . C4 C 0.41178(13) 0.45730(11) 0.7362(5) 0.0239(6) Uani 1 1 d . . . C5 C 0.42295(12) 0.40594(10) 0.6956(4) 0.0200(6) Uani 1 1 d . . . C6 C 0.46452(12) 0.38982(10) 0.5858(4) 0.0183(6) Uani 1 1 d . . . C7 C 0.47813(13) 0.33663(10) 0.5527(5) 0.0233(6) Uani 1 1 d . . . H7 H 0.4599 0.3069 0.5967 0.028 Uiso 1 1 calc R . . N51 N 0.31118(11) 0.29311(9) 0.8962(4) 0.0267(6) Uani 1 1 d . . . C52 C 0.30210(15) 0.30601(13) 0.6874(5) 0.0335(8) Uani 1 1 d . . . H52 H 0.2694 0.2902 0.5825 0.040 Uiso 1 1 calc R . . C53 C 0.33830(14) 0.34125(13) 0.6185(5) 0.0320(7) Uani 1 1 d . . . H53 H 0.3305 0.3489 0.4686 0.038 Uiso 1 1 calc R . . C54 C 0.38592(12) 0.36541(10) 0.7666(5) 0.0217(6) Uani 1 1 d . . . C55 C 0.39614(14) 0.35106(12) 0.9818(5) 0.0301(7) Uani 1 1 d . . . H55 H 0.4290 0.3659 1.0893 0.036 Uiso 1 1 calc R . . C56 C 0.35848(14) 0.31524(12) 1.0394(5) 0.0315(7) Uani 1 1 d . . . H56 H 0.3664 0.3058 1.1876 0.038 Uiso 1 1 calc R . . Cu2 Cu 0.2500 0.2500 1.0000 0.02638(18) Uani 1 2 d S . . F111 F 0.43824(10) 0.21308(9) 1.4893(4) 0.0664(7) Uani 1 1 d . . . F112 F 0.37255(12) 0.19441(13) 1.6512(4) 0.0824(9) Uani 1 1 d . . . F113 F 0.41929(15) 0.13432(10) 1.5337(5) 0.0994(11) Uani 1 1 d . . . F151 F 0.28664(15) 0.09520(11) 0.5958(5) 0.0874(9) Uani 1 1 d . . . F152 F 0.2378(2) 0.06595(12) 0.8067(6) 0.1205(14) Uani 1 1 d . . . F153 F 0.3355(2) 0.05589(12) 0.8791(6) 0.1391(17) Uani 1 1 d . . . O12 O 0.31709(10) 0.22635(8) 1.2485(3) 0.0320(5) Uani 1 1 d . . . O13 O 0.26454(11) 0.17557(9) 0.8295(4) 0.0383(6) Uani 1 1 d . . . C11 C 0.39346(18) 0.18097(14) 1.4910(7) 0.0498(10) Uani 1 1 d . . . C12 C 0.34433(15) 0.18307(13) 1.2741(6) 0.0391(8) Uani 1 1 d . . . C13 C 0.33669(18) 0.14084(13) 1.1377(6) 0.0496(10) Uani 1 1 d . . . H13 H 0.3599 0.1105 1.1882 0.059 Uiso 1 1 calc R . . C14 C 0.29695(18) 0.13998(14) 0.9301(6) 0.0456(9) Uani 1 1 d . . . C15 C 0.2900(3) 0.08786(17) 0.8041(8) 0.0737(14) 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 Cu1 0.0189(4) 0.0080(4) 0.0289(4) 0.000 0.0185(4) 0.000 N21 0.0243(17) 0.0098(16) 0.037(2) 0.000 0.0202(16) 0.000 N22 0.0183(16) 0.0140(16) 0.0240(17) 0.000 0.0173(14) 0.000 C3 0.0404(18) 0.0238(16) 0.061(2) 0.0015(15) 0.0442(18) -0.0024(14) C4 0.0264(15) 0.0150(14) 0.0384(17) 0.0002(12) 0.0227(13) -0.0035(11) C5 0.0235(14) 0.0160(14) 0.0262(15) 0.0009(11) 0.0165(12) -0.0054(11) C6 0.0221(14) 0.0133(13) 0.0241(14) 0.0003(11) 0.0141(12) -0.0051(11) C7 0.0325(15) 0.0100(14) 0.0319(16) -0.0006(11) 0.0165(13) -0.0042(12) N51 0.0329(14) 0.0216(13) 0.0301(14) -0.0006(10) 0.0163(12) -0.0097(11) C52 0.0410(18) 0.0355(19) 0.0281(16) -0.0050(14) 0.0162(15) -0.0213(15) C53 0.0386(18) 0.0356(19) 0.0284(16) -0.0008(14) 0.0203(15) -0.0192(14) C54 0.0263(16) 0.0158(15) 0.0307(16) -0.0022(12) 0.0209(13) -0.0047(11) C55 0.0298(16) 0.0311(18) 0.0318(17) 0.0027(13) 0.0124(14) -0.0151(13) C56 0.0350(18) 0.0313(18) 0.0304(16) 0.0060(13) 0.0130(14) -0.0111(14) Cu2 0.0310(3) 0.0213(3) 0.0321(3) 0.0024(3) 0.0176(3) -0.0115(3) F111 0.0454(13) 0.0573(16) 0.0900(18) -0.0034(13) 0.0077(13) -0.0133(11) F112 0.0725(17) 0.128(3) 0.0440(14) 0.0118(15) 0.0108(13) 0.0004(17) F113 0.117(2) 0.0393(15) 0.102(2) 0.0099(14) -0.0381(19) 0.0110(15) F151 0.126(3) 0.0611(18) 0.0786(19) -0.0285(15) 0.0331(18) 0.0054(17) F152 0.195(4) 0.0561(19) 0.130(3) -0.0337(18) 0.076(3) -0.069(2) F153 0.207(4) 0.0496(18) 0.123(3) -0.0266(18) -0.019(3) 0.053(2) O12 0.0360(12) 0.0238(12) 0.0417(13) 0.0039(9) 0.0198(10) -0.0097(9) O13 0.0500(14) 0.0298(13) 0.0417(13) -0.0002(10) 0.0237(12) -0.0060(11) C11 0.050(2) 0.031(2) 0.065(3) 0.0097(18) 0.010(2) -0.0077(17) C12 0.0382(19) 0.031(2) 0.049(2) 0.0110(15) 0.0153(17) -0.0111(15) C13 0.063(3) 0.0203(19) 0.062(3) 0.0045(17) 0.012(2) 0.0011(17) C14 0.059(2) 0.0276(19) 0.054(2) -0.0016(17) 0.023(2) -0.0045(17) C15 0.104(4) 0.033(2) 0.077(4) -0.004(2) 0.015(3) 0.002(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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N22 1.990(3) 5_666 ? Cu1 N22 1.990(3) . ? Cu1 N21 1.999(3) . ? Cu1 N21 1.999(3) 2_656 ? N21 C4 1.380(3) . ? N21 C4 1.380(3) 6_565 ? N22 C6 1.384(3) . ? N22 C6 1.384(3) 2_656 ? C3 C3 1.341(6) 6_565 ? C3 C4 1.439(4) . ? C4 C5 1.384(4) . ? C5 C6 1.392(4) . ? C5 C54 1.491(4) . ? C6 C7 1.432(4) . ? C7 C7 1.352(5) 2_656 ? N51 C56 1.339(4) . ? N51 C52 1.341(4) . ? N51 Cu2 2.034(2) . ? C52 C53 1.379(4) . ? C53 C54 1.381(4) . ? C54 C55 1.387(4) . ? C55 C56 1.378(4) . ? Cu2 O12 1.981(2) 7_557 ? Cu2 O12 1.981(2) . ? Cu2 N51 2.034(2) 7_557 ? Cu2 O13 2.275(2) . ? Cu2 O13 2.275(2) 7_557 ? F111 C11 1.317(4) . ? F111 F111 2.786(5) 2_658 ? F112 C11 1.294(5) . ? F113 C11 1.332(5) . ? F151 C15 1.333(6) . ? F152 C15 1.323(6) . ? F153 C15 1.309(6) . ? O12 C12 1.264(4) . ? O13 C14 1.241(4) . ? C11 C12 1.532(5) . ? C12 C13 1.376(5) . ? C13 C14 1.393(5) . ? C14 C15 1.551(6) . ? 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 N22 Cu1 N22 180.0 5_666 . ? N22 Cu1 N21 90.00(1) 5_666 . ? N22 Cu1 N21 90.00(1) . . ? N22 Cu1 N21 90.00(1) 5_666 2_656 ? N22 Cu1 N21 90.00(1) . 2_656 ? N21 Cu1 N21 180.00(1) . 2_656 ? C4 N21 C4 105.4(3) . 6_565 ? C4 N21 Cu1 127.23(15) . . ? C4 N21 Cu1 127.23(15) 6_565 . ? C6 N22 C6 104.9(3) . 2_656 ? C6 N22 Cu1 127.57(15) . . ? C6 N22 Cu1 127.57(15) 2_656 . ? C3 C3 C4 107.30(16) 6_565 . ? N21 C4 C5 125.5(2) . . ? N21 C4 C3 110.0(2) . . ? C5 C4 C3 124.4(2) . . ? C4 C5 C6 124.5(2) . . ? C4 C5 C54 117.4(2) . . ? C6 C5 C54 118.0(2) . . ? N22 C6 C5 125.1(2) . . ? N22 C6 C7 110.5(2) . . ? C5 C6 C7 124.4(2) . . ? C7 C7 C6 107.12(15) 2_656 . ? C56 N51 C52 117.2(2) . . ? C56 N51 Cu2 120.24(19) . . ? C52 N51 Cu2 122.1(2) . . ? N51 C52 C53 122.8(3) . . ? C52 C53 C54 120.2(3) . . ? C53 C54 C55 116.9(2) . . ? C53 C54 C5 120.6(3) . . ? C55 C54 C5 122.4(3) . . ? C56 C55 C54 119.9(3) . . ? N51 C56 C55 123.0(3) . . ? O12 Cu2 O12 180.0 7_557 . ? O12 Cu2 N51 91.00(9) 7_557 . ? O12 Cu2 N51 89.00(9) . . ? O12 Cu2 N51 89.00(9) 7_557 7_557 ? O12 Cu2 N51 91.00(9) . 7_557 ? N51 Cu2 N51 180.00(12) . 7_557 ? O12 Cu2 O13 93.06(9) 7_557 . ? O12 Cu2 O13 86.94(9) . . ? N51 Cu2 O13 95.58(9) . . ? N51 Cu2 O13 84.42(9) 7_557 . ? O12 Cu2 O13 86.94(9) 7_557 7_557 ? O12 Cu2 O13 93.06(9) . 7_557 ? N51 Cu2 O13 84.42(9) . 7_557 ? N51 Cu2 O13 95.58(9) 7_557 7_557 ? O13 Cu2 O13 180.0 . 7_557 ? C11 F111 F111 141.0(2) . 2_658 ? C12 O12 Cu2 128.3(2) . . ? C14 O13 Cu2 121.0(2) . . ? F112 C11 F111 107.2(3) . . ? F112 C11 F113 108.4(4) . . ? F111 C11 F113 105.4(3) . . ? F112 C11 C12 112.1(3) . . ? F111 C11 C12 110.3(3) . . ? F113 C11 C12 113.0(3) . . ? O12 C12 C13 129.8(4) . . ? O12 C12 C11 111.2(3) . . ? C13 C12 C11 119.0(3) . . ? C12 C13 C14 123.9(4) . . ? O13 C14 C13 128.7(3) . . ? O13 C14 C15 113.9(4) . . ? C13 C14 C15 117.4(4) . . ? F153 C15 F152 110.8(4) . . ? F153 C15 F151 106.3(5) . . ? F152 C15 F151 105.6(4) . . ? F153 C15 C14 113.2(4) . . ? F152 C15 C14 109.0(4) . . ? F151 C15 C14 111.8(4) . . ? 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 C3 H3 F152 0.95 2.98 3.846(4) 151.8 7_557 C7 H7 F111 0.95 2.52 3.301(3) 139.3 1_554 C52 H52 O13 0.95 2.69 3.286(4) 121.0 7_556 C53 H53 O13 0.95 2.55 3.206(4) 126.5 7_556 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 65.55 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.551 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.070 # 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 0.500 -0.042 406 57 '6 H2O' 2 0.500 0.000 0.027 406 57 '6 H2O' _platon_squeeze_details ; ;