# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2006 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Bradley Smith' _publ_contact_author_address ; Dept of Chemistry and Biochemistry University of Notre Dame Notre Dame IN 46556 UNITED STATES OF AMERICA ; _publ_contact_author_email SMITH.115@ND.EDU _publ_section_title ; Singlet Oxygen Generation Using Iodinated Squaraine and Squaraine-Rotaxane Dyes ; loop_ _publ_author_name 'Bradley Smith' 'Easwaran Arunkumar' 'Prashant Kamat' 'Bruce C. Noll' 'Pallikkara Sudeep' # Attachment 'bcn263_0m.cif' data_bcn263_0m _database_code_depnum_ccdc_archive 'CCDC 626189' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H32 I4 N2 O2, 2(C H Cl3)' _chemical_formula_sum 'C46 H34 Cl6 I4 N2 O2' _chemical_formula_weight 1367.05 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_int_tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 14.2033(3) _cell_length_b 16.4470(4) _cell_length_c 20.4164(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4769.31(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6322 _cell_measurement_theta_min 2.4767 _cell_measurement_theta_max 28.6811 _exptl_crystal_description plate _exptl_crystal_colour 'translucent intense blue gold' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.904 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2616 _exptl_absorpt_coefficient_mu 2.989 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6258 _exptl_absorpt_correction_T_max 0.8872 _exptl_absorpt_process_details ;Blessing, R. H. (1985) Acta Cryst. A51, 33-38. Sheldrick, G. M. (2005) SADABS. University of G\:ottingen, Germany. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Siemens KFFMO2K-90' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker d8-ApexII CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 56848 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.40 _reflns_number_total 4884 _reflns_number_gt 4049 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004; Sheldrick, 2003)' _computing_structure_solution 'XS (Sheldrick, 2001)' _computing_structure_refinement 'XL (Sheldrick, 2001)' _computing_molecular_graphics 'XP (Sheldrick, 1998)' _computing_publication_material 'XCIF (Sheldrick, 2001)/enCIFer (CCDC, 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^)+(0.0225P)^2^+4.0046P] 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 4884 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0213 _refine_ls_wR_factor_ref 0.0512 _refine_ls_wR_factor_gt 0.0467 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _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 I1 I 0.304217(13) 0.297217(13) 0.704379(9) 0.03060(6) Uani 1 1 d . . . I2 I 0.947998(13) -0.179831(10) 0.421415(9) 0.02560(6) Uani 1 1 d . . . N1 N 0.73966(14) 0.17588(13) 0.56494(10) 0.0195(4) Uani 1 1 d . . . O1 O 1.00142(13) 0.53398(11) 0.60775(9) 0.0225(4) Uani 1 1 d . . . C1 C 1.00105(17) 0.51515(15) 0.54916(12) 0.0173(5) Uani 1 1 d . . . C2 C 0.95798(16) 0.45005(15) 0.51050(12) 0.0164(5) Uani 1 1 d . . . C3 C 0.90155(17) 0.38239(15) 0.52467(12) 0.0171(5) Uani 1 1 d . . . C4 C 0.87205(17) 0.36483(15) 0.58911(12) 0.0188(5) Uani 1 1 d . . . H4 H 0.8897 0.4002 0.6238 0.023 Uiso 1 1 calc R . . C5 C 0.81849(17) 0.29789(16) 0.60255(13) 0.0199(5) Uani 1 1 d . . . H5 H 0.7988 0.2876 0.6462 0.024 Uiso 1 1 calc R . . C6 C 0.79186(16) 0.24330(15) 0.55162(12) 0.0173(5) Uani 1 1 d . . . C7 C 0.82075(17) 0.26145(15) 0.48716(12) 0.0185(5) Uani 1 1 d . . . H7 H 0.8036 0.2261 0.4524 0.022 Uiso 1 1 calc R . . C8 C 0.87293(17) 0.32910(15) 0.47411(12) 0.0186(5) Uani 1 1 d . . . H8 H 0.8904 0.3407 0.4302 0.022 Uiso 1 1 calc R . . C9 C 0.70859(18) 0.15617(15) 0.63111(13) 0.0205(5) Uani 1 1 d . . . H9A H 0.7585 0.1725 0.6623 0.025 Uiso 1 1 calc R . . H9B H 0.7009 0.0965 0.6345 0.025 Uiso 1 1 calc R . . C10 C 0.61689(18) 0.19658(15) 0.65146(13) 0.0193(5) Uani 1 1 d . . . C11 C 0.57582(17) 0.25740(15) 0.61390(12) 0.0187(5) Uani 1 1 d . . . H11 H 0.6080 0.2782 0.5767 0.022 Uiso 1 1 calc R . . C12 C 0.48758(18) 0.28803(16) 0.63065(12) 0.0196(5) Uani 1 1 d . . . H12 H 0.4597 0.3300 0.6053 0.024 Uiso 1 1 calc R . . C13 C 0.44117(17) 0.25695(16) 0.68430(12) 0.0209(5) Uani 1 1 d . . . C14 C 0.48261(19) 0.19862(16) 0.72396(13) 0.0220(6) Uani 1 1 d . . . H14 H 0.4510 0.1792 0.7619 0.026 Uiso 1 1 calc R . . C15 C 0.57081(19) 0.16912(15) 0.70744(13) 0.0216(5) Uani 1 1 d . . . H15 H 0.6002 0.1297 0.7346 0.026 Uiso 1 1 calc R . . C16 C 0.70087(17) 0.12549(15) 0.51255(13) 0.0205(5) Uani 1 1 d . . . H16A H 0.6868 0.1607 0.4744 0.025 Uiso 1 1 calc R . . H16B H 0.6406 0.1018 0.5277 0.025 Uiso 1 1 calc R . . C17 C 0.76501(17) 0.05682(15) 0.49026(12) 0.0184(5) Uani 1 1 d . . . C18 C 0.83530(19) 0.02528(16) 0.53020(13) 0.0237(6) Uani 1 1 d . . . H18 H 0.8475 0.0499 0.5714 0.028 Uiso 1 1 calc R . . C19 C 0.88806(19) -0.04164(16) 0.51085(13) 0.0237(6) Uani 1 1 d . . . H19 H 0.9359 -0.0628 0.5386 0.028 Uiso 1 1 calc R . . C20 C 0.86987(18) -0.07732(15) 0.45010(13) 0.0202(5) Uani 1 1 d . . . C21 C 0.80120(18) -0.04579(16) 0.40927(13) 0.0223(5) Uani 1 1 d . . . H21 H 0.7897 -0.0697 0.3677 0.027 Uiso 1 1 calc R . . C22 C 0.74925(18) 0.02104(16) 0.42962(13) 0.0225(6) Uani 1 1 d . . . H22 H 0.7021 0.0427 0.4016 0.027 Uiso 1 1 calc R . . C23 C 0.0718(2) 0.47857(17) 0.73872(14) 0.0267(6) Uani 1 1 d . . . H23 H 0.0481 0.5132 0.7020 0.032 Uiso 1 1 calc R . . Cl1 Cl 0.18649(6) 0.51073(5) 0.75931(5) 0.0476(2) Uani 1 1 d . . . Cl2 Cl -0.00408(6) 0.49064(5) 0.80622(4) 0.0413(2) Uani 1 1 d . . . Cl3 Cl 0.07347(5) 0.37668(4) 0.71235(3) 0.02712(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 I1 0.02412(10) 0.04860(13) 0.01907(9) 0.00100(8) 0.00305(7) 0.00750(8) I2 0.03078(10) 0.02031(9) 0.02572(10) 0.00091(7) 0.00410(7) 0.00338(7) N1 0.0177(10) 0.0191(11) 0.0217(11) 0.0001(9) 0.0019(9) -0.0021(9) O1 0.0326(10) 0.0197(9) 0.0153(9) -0.0015(7) 0.0011(8) -0.0003(8) C1 0.0179(12) 0.0138(12) 0.0202(13) 0.0006(10) 0.0009(10) 0.0037(10) C2 0.0153(11) 0.0146(12) 0.0193(12) -0.0010(9) 0.0000(10) 0.0050(9) C3 0.0171(12) 0.0155(12) 0.0186(12) -0.0001(10) 0.0009(10) 0.0034(10) C4 0.0201(12) 0.0197(13) 0.0167(12) -0.0041(10) -0.0029(10) 0.0015(10) C5 0.0211(13) 0.0211(13) 0.0174(13) 0.0012(10) 0.0016(10) -0.0014(10) C6 0.0145(11) 0.0160(12) 0.0215(13) -0.0002(10) -0.0001(10) 0.0014(9) C7 0.0206(13) 0.0170(12) 0.0181(13) -0.0034(10) -0.0006(10) 0.0006(10) C8 0.0221(12) 0.0177(13) 0.0159(12) 0.0007(10) -0.0003(10) 0.0034(10) C9 0.0218(13) 0.0153(12) 0.0242(14) 0.0052(10) -0.0003(10) -0.0033(10) C10 0.0223(13) 0.0162(13) 0.0195(13) -0.0011(10) -0.0015(10) -0.0046(10) C11 0.0185(12) 0.0209(13) 0.0165(12) 0.0014(10) -0.0005(10) -0.0046(10) C12 0.0216(12) 0.0204(13) 0.0169(12) -0.0005(10) -0.0046(10) -0.0015(10) C13 0.0182(12) 0.0254(14) 0.0193(13) -0.0058(10) -0.0013(10) -0.0016(11) C14 0.0278(14) 0.0223(14) 0.0160(13) -0.0014(10) 0.0018(10) -0.0059(11) C15 0.0273(14) 0.0171(13) 0.0203(13) 0.0036(10) -0.0023(11) -0.0015(10) C16 0.0183(12) 0.0183(13) 0.0248(14) -0.0017(10) -0.0019(10) -0.0045(10) C17 0.0189(12) 0.0153(13) 0.0209(13) 0.0025(10) 0.0016(10) -0.0057(10) C18 0.0249(13) 0.0226(14) 0.0235(14) -0.0021(11) -0.0028(11) 0.0004(11) C19 0.0265(14) 0.0215(14) 0.0231(14) 0.0035(11) -0.0021(11) 0.0009(11) C20 0.0214(12) 0.0149(12) 0.0244(13) 0.0017(10) 0.0043(11) -0.0014(10) C21 0.0243(13) 0.0228(14) 0.0199(13) -0.0008(10) 0.0008(11) -0.0020(11) C22 0.0219(13) 0.0226(14) 0.0231(14) 0.0051(11) -0.0029(11) -0.0027(10) C23 0.0360(16) 0.0214(14) 0.0227(14) 0.0004(11) 0.0035(12) -0.0009(12) Cl1 0.0476(5) 0.0447(5) 0.0505(5) -0.0137(4) -0.0090(4) -0.0138(4) Cl2 0.0643(5) 0.0301(4) 0.0295(4) 0.0069(3) 0.0187(4) 0.0175(4) Cl3 0.0272(3) 0.0222(3) 0.0320(4) -0.0033(3) 0.0039(3) -0.0011(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 I1 C13 2.095(3) . ? I2 C20 2.102(3) . ? N1 C6 1.361(3) . ? N1 C9 1.458(3) . ? N1 C16 1.461(3) . ? O1 C1 1.236(3) . ? C1 C2 1.464(3) . ? C1 C2 1.466(3) 5_766 ? C2 C3 1.401(3) . ? C2 C1 1.466(3) 5_766 ? C3 C4 1.411(3) . ? C3 C8 1.414(4) . ? C4 C5 1.366(4) . ? C4 H4 0.9500 . ? C5 C6 1.425(4) . ? C5 H5 0.9500 . ? C6 C7 1.410(4) . ? C7 C8 1.363(4) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.520(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.389(4) . ? C10 C15 1.392(4) . ? C11 C12 1.393(4) . ? C11 H11 0.9500 . ? C12 C13 1.377(4) . ? C12 H12 0.9500 . ? C13 C14 1.386(4) . ? C14 C15 1.385(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.521(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C22 1.389(4) . ? C17 C18 1.389(4) . ? C18 C19 1.389(4) . ? C18 H18 0.9500 . ? C19 C20 1.396(4) . ? C19 H19 0.9500 . ? C20 C21 1.384(4) . ? C21 C22 1.388(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 Cl3 1.760(3) . ? C23 Cl2 1.760(3) . ? C23 Cl1 1.764(3) . ? C23 H23 1.0000 . ? 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 C6 N1 C9 122.1(2) . . ? C6 N1 C16 121.4(2) . . ? C9 N1 C16 116.0(2) . . ? O1 C1 C2 135.0(2) . . ? O1 C1 C2 134.8(2) . 5_766 ? C2 C1 C2 90.2(2) . 5_766 ? C3 C2 C1 135.1(2) . . ? C3 C2 C1 135.1(2) . 5_766 ? C1 C2 C1 89.8(2) . 5_766 ? C2 C3 C4 121.7(2) . . ? C2 C3 C8 120.4(2) . . ? C4 C3 C8 117.9(2) . . ? C5 C4 C3 121.2(2) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 120.6(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? N1 C6 C7 121.1(2) . . ? N1 C6 C5 120.8(2) . . ? C7 C6 C5 118.1(2) . . ? C8 C7 C6 120.9(2) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C3 121.3(2) . . ? C7 C8 H8 119.3 . . ? C3 C8 H8 119.3 . . ? N1 C9 C10 114.5(2) . . ? N1 C9 H9A 108.6 . . ? C10 C9 H9A 108.6 . . ? N1 C9 H9B 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C11 C10 C15 119.3(2) . . ? C11 C10 C9 121.6(2) . . ? C15 C10 C9 119.0(2) . . ? C10 C11 C12 120.2(2) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 119.4(2) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 121.2(2) . . ? C12 C13 I1 118.86(19) . . ? C14 C13 I1 119.90(19) . . ? C15 C14 C13 119.0(2) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C10 120.8(2) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? N1 C16 C17 114.5(2) . . ? N1 C16 H16A 108.6 . . ? C17 C16 H16A 108.6 . . ? N1 C16 H16B 108.6 . . ? C17 C16 H16B 108.6 . . ? H16A C16 H16B 107.6 . . ? C22 C17 C18 118.7(2) . . ? C22 C17 C16 119.0(2) . . ? C18 C17 C16 122.1(2) . . ? C19 C18 C17 121.1(3) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C18 C19 C20 119.1(2) . . ? C18 C19 H19 120.5 . . ? C20 C19 H19 120.5 . . ? C21 C20 C19 120.5(2) . . ? C21 C20 I2 120.32(19) . . ? C19 C20 I2 119.14(19) . . ? C20 C21 C22 119.4(2) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C21 C22 C17 121.1(2) . . ? C21 C22 H22 119.4 . . ? C17 C22 H22 119.4 . . ? Cl3 C23 Cl2 110.81(15) . . ? Cl3 C23 Cl1 110.22(16) . . ? Cl2 C23 Cl1 110.18(15) . . ? Cl3 C23 H23 108.5 . . ? Cl2 C23 H23 108.5 . . ? Cl1 C23 H23 108.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.489 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.086 _chemical_compound_source synthesized