# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Yoshitane Imai' _publ_contact_author_email Y-IMAI@APCH.KINDAI.AC.JP _publ_section_title ; Control of crystal structure and solid-state chiral optical properties of chiral supramolecular organic fluorophore consisting of 1-pyrenesulfonic acid and chiral amine molecules ; loop_ _publ_author_name 'Yoshitane Imai' 'Michiya Fujiki' 'Takunori Harada' 'Takafumi Kinuta' 'Reiko Kuroda' 'Yoshio Matsubara' ; K.Murata ; 'Yoko Nakano' 'Tomohiro Sato' 'Nobuo Tajima' # Attachment 'N-IMAI814.CIF' data_Nimai814_1 _database_code_depnum_ccdc_archive 'CCDC 743140' #TrackingRef 'N-IMAI814.CIF' #data_im7615a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H23 N O3 S' _chemical_formula_weight 453.53 _chemical_absolute_configuration ad 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' S S 0.1246 0.1234 '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 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' _cell_length_a 20.575(2) _cell_length_b 5.5363(5) _cell_length_c 18.7917(19) _cell_angle_alpha 90.00 _cell_angle_beta 91.676(2) _cell_angle_gamma 90.00 _cell_volume 2139.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3812 _cell_measurement_theta_min 1.98 _cell_measurement_theta_max 27.86 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.184 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9217 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6689 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0665 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.86 _reflns_number_total 4430 _reflns_number_gt 3812 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0512P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(9) _refine_ls_number_reflns 4430 _refine_ls_number_parameters 300 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.1025 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 C1 C 0.92141(12) 0.9775(5) 0.80875(13) 0.0167(6) Uani 1 1 d . . . C2 C 0.95005(12) 0.8182(5) 0.76220(14) 0.0177(6) Uani 1 1 d . . . H2 H 0.9766 0.6909 0.7805 0.021 Uiso 1 1 calc R . . C3 C 0.94041(12) 0.8423(5) 0.68936(14) 0.0199(6) Uani 1 1 d . . . H3 H 0.9602 0.7304 0.6584 0.024 Uiso 1 1 calc R . . C4 C 0.90239(13) 1.0271(5) 0.66090(14) 0.0183(6) Uani 1 1 d . . . C5 C 0.83136(12) 1.3792(5) 0.67942(13) 0.0163(6) Uani 1 1 d . . . C6 C 0.80110(13) 1.5449(5) 0.72558(15) 0.0181(6) Uani 1 1 d . . . C7 C 0.81194(13) 1.5190(5) 0.80027(15) 0.0193(6) Uani 1 1 d . . . H7 H 0.7924 1.6307 0.8315 0.023 Uiso 1 1 calc R . . C8 C 0.84936(13) 1.3395(5) 0.82786(14) 0.0179(6) Uani 1 1 d . . . H8 H 0.8548 1.3260 0.8781 0.021 Uiso 1 1 calc R . . C9 C 0.88112(12) 1.1680(5) 0.78293(14) 0.0152(6) Uani 1 1 d . . . C10 C 0.87143(12) 1.1920(5) 0.70816(14) 0.0165(6) Uani 1 1 d . . . C11 C 0.89277(14) 1.0622(5) 0.58579(15) 0.0238(7) Uani 1 1 d . . . H11 H 0.9141 0.9573 0.5540 0.029 Uiso 1 1 calc R . . C12 C 0.85469(13) 1.2380(6) 0.55881(14) 0.0238(7) Uani 1 1 d . . . H12 H 0.8494 1.2534 0.5086 0.029 Uiso 1 1 calc R . . C13 C 0.82175(12) 1.4035(5) 0.60420(14) 0.0197(6) Uani 1 1 d . . . C14 C 0.78194(14) 1.5885(6) 0.57786(16) 0.0250(7) Uani 1 1 d . . . H14 H 0.7750 1.6050 0.5279 0.030 Uiso 1 1 calc R . . C15 C 0.75248(13) 1.7481(6) 0.62319(16) 0.0255(7) Uani 1 1 d . . . H15 H 0.7253 1.8721 0.6040 0.031 Uiso 1 1 calc R . . C16 C 0.76204(13) 1.7298(5) 0.69598(16) 0.0226(6) Uani 1 1 d . . . H16 H 0.7421 1.8432 0.7264 0.027 Uiso 1 1 calc R . . S1 S 0.93979(3) 0.94485(13) 0.90121(3) 0.01791(15) Uani 1 1 d . . . O1 O 0.96725(9) 1.1762(4) 0.92346(10) 0.0223(5) Uani 1 1 d . . . O2 O 0.98639(10) 0.7486(4) 0.90665(11) 0.0269(5) Uani 1 1 d . . . O3 O 0.87945(8) 0.8900(3) 0.93668(9) 0.0224(5) Uani 1 1 d . . . C21 C 0.58932(13) -0.1699(5) 0.79601(14) 0.0201(6) Uani 1 1 d . . . H21 H 0.5662 -0.3154 0.8041 0.024 Uiso 1 1 calc R . . C22 C 0.62161(11) -0.0601(6) 0.85148(13) 0.0180(5) Uani 1 1 d . . . C23 C 0.65496(14) 0.1588(5) 0.83960(16) 0.0234(6) Uani 1 1 d . . . H23 H 0.6772 0.2366 0.8782 0.028 Uiso 1 1 calc R . . C24 C 0.65555(13) 0.2592(6) 0.77385(15) 0.0237(6) Uani 1 1 d . . . H24 H 0.6777 0.4078 0.7672 0.028 Uiso 1 1 calc R . . C25 C 0.62555(14) 0.2444(6) 0.64530(16) 0.0275(7) Uani 1 1 d . . . H25 H 0.6485 0.3902 0.6371 0.033 Uiso 1 1 calc R . . C26 C 0.59406(14) 0.1289(6) 0.58984(16) 0.0286(7) Uani 1 1 d . . . H26 H 0.5954 0.1950 0.5432 0.034 Uiso 1 1 calc R . . C27 C 0.55986(13) -0.0862(7) 0.60120(15) 0.0287(7) Uani 1 1 d . . . H27 H 0.5380 -0.1640 0.5623 0.034 Uiso 1 1 calc R . . C28 C 0.55770(13) -0.1845(6) 0.66761(15) 0.0250(7) Uani 1 1 d . . . H28 H 0.5346 -0.3307 0.6747 0.030 Uiso 1 1 calc R . . C29 C 0.58964(11) -0.0703(6) 0.72591(13) 0.0189(5) Uani 1 1 d . . . C30 C 0.62384(13) 0.1465(5) 0.71501(15) 0.0204(6) Uani 1 1 d . . . C31 C 0.62176(12) -0.1745(5) 0.92450(13) 0.0192(6) Uani 1 1 d . . . H31 H 0.6002 -0.3358 0.9199 0.023 Uiso 1 1 calc R . . C32 C 0.68923(13) -0.2136(6) 0.95760(15) 0.0269(7) Uani 1 1 d . . . H32A H 0.7154 -0.3085 0.9250 0.040 Uiso 1 1 calc R . . H32B H 0.6856 -0.3007 1.0027 0.040 Uiso 1 1 calc R . . H32C H 0.7101 -0.0569 0.9664 0.040 Uiso 1 1 calc R . . N33 N 0.58250(10) -0.0232(4) 0.97414(11) 0.0179(5) Uani 1 1 d . . . H33A H 0.6077 0.0984 0.9923 0.027 Uiso 1 1 calc R . . H33B H 0.5684 -0.1171 1.0103 0.027 Uiso 1 1 calc R . . H33C H 0.5477 0.0406 0.9498 0.027 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 C1 0.0160(12) 0.0173(16) 0.0169(13) 0.0017(12) -0.0004(10) -0.0029(12) C2 0.0167(13) 0.0127(14) 0.0238(15) 0.0012(12) 0.0016(11) 0.0007(11) C3 0.0187(13) 0.0184(14) 0.0229(14) -0.0050(12) 0.0049(11) -0.0027(11) C4 0.0183(14) 0.0185(15) 0.0183(14) -0.0035(11) 0.0025(11) -0.0059(11) C5 0.0125(12) 0.0192(16) 0.0171(13) 0.0013(10) -0.0028(10) -0.0047(10) C6 0.0122(13) 0.0193(14) 0.0228(15) 0.0048(12) 0.0004(11) -0.0018(10) C7 0.0173(14) 0.0215(17) 0.0193(14) -0.0020(11) 0.0013(11) 0.0001(11) C8 0.0197(13) 0.0194(14) 0.0145(13) -0.0002(11) 0.0004(11) -0.0031(12) C9 0.0148(13) 0.0154(14) 0.0154(13) 0.0002(11) -0.0013(10) -0.0030(10) C10 0.0126(13) 0.0187(15) 0.0182(14) -0.0008(11) 0.0005(10) -0.0059(11) C11 0.0252(16) 0.0283(17) 0.0181(15) -0.0077(13) 0.0037(12) -0.0066(13) C12 0.0266(15) 0.0325(17) 0.0125(13) -0.0015(13) 0.0016(11) -0.0113(14) C13 0.0178(13) 0.0223(18) 0.0189(13) 0.0043(12) -0.0027(10) -0.0083(12) C14 0.0228(16) 0.0294(18) 0.0225(16) 0.0098(14) -0.0069(12) -0.0072(13) C15 0.0196(15) 0.0227(16) 0.0337(17) 0.0111(14) -0.0074(12) -0.0012(13) C16 0.0173(14) 0.0188(15) 0.0316(16) 0.0026(13) 0.0005(12) -0.0010(12) S1 0.0206(3) 0.0173(3) 0.0157(3) 0.0020(3) -0.0027(2) 0.0022(3) O1 0.0238(11) 0.0248(12) 0.0178(10) -0.0016(8) -0.0044(8) -0.0023(9) O2 0.0316(12) 0.0245(12) 0.0244(11) 0.0046(10) -0.0034(9) 0.0102(10) O3 0.0244(10) 0.0237(13) 0.0190(9) 0.0034(8) 0.0014(7) -0.0006(8) C21 0.0198(13) 0.0165(14) 0.0241(15) 0.0035(12) 0.0035(11) -0.0010(11) C22 0.0177(12) 0.0175(13) 0.0191(12) 0.0021(14) 0.0024(10) 0.0027(13) C23 0.0249(15) 0.0181(16) 0.0270(16) -0.0044(12) -0.0007(12) -0.0031(12) C24 0.0243(15) 0.0145(14) 0.0326(17) 0.0008(13) 0.0041(12) -0.0022(12) C25 0.0278(16) 0.0235(16) 0.0317(17) 0.0075(14) 0.0121(13) 0.0062(13) C26 0.0337(18) 0.0327(19) 0.0200(15) 0.0117(14) 0.0083(13) 0.0124(15) C27 0.0275(14) 0.037(2) 0.0219(14) -0.0049(15) -0.0026(11) 0.0086(15) C28 0.0210(14) 0.0291(17) 0.0251(15) 0.0008(13) 0.0013(12) 0.0010(13) C29 0.0170(12) 0.0170(14) 0.0227(13) 0.0020(14) 0.0030(10) 0.0043(13) C30 0.0196(14) 0.0204(15) 0.0215(15) 0.0018(12) 0.0060(11) 0.0058(12) C31 0.0212(14) 0.0168(14) 0.0197(14) -0.0023(12) 0.0021(11) 0.0020(12) C32 0.0239(15) 0.0293(18) 0.0278(16) 0.0043(14) 0.0027(12) 0.0061(13) N33 0.0158(10) 0.0185(13) 0.0192(11) -0.0007(10) -0.0016(8) 0.0032(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 C1 C2 1.386(4) . ? C1 C9 1.418(4) . ? C1 S1 1.777(3) . ? C2 C3 1.384(4) . ? C3 C4 1.386(4) . ? C4 C11 1.433(4) . ? C4 C10 1.436(4) . ? C5 C6 1.419(4) . ? C5 C10 1.421(4) . ? C5 C13 1.428(3) . ? C6 C16 1.406(4) . ? C6 C7 1.422(4) . ? C7 C8 1.352(4) . ? C8 C9 1.440(4) . ? C9 C10 1.420(3) . ? C11 C12 1.340(4) . ? C12 C13 1.435(4) . ? C13 C14 1.393(4) . ? C14 C15 1.380(4) . ? C15 C16 1.380(4) . ? S1 O2 1.451(2) . ? S1 O1 1.456(2) . ? S1 O3 1.4580(19) . ? C21 C22 1.363(4) . ? C21 C29 1.428(4) . ? C22 C23 1.414(4) . ? C22 C31 1.511(4) . ? C23 C24 1.355(4) . ? C24 C30 1.413(4) . ? C25 C26 1.370(4) . ? C25 C30 1.419(4) . ? C26 C27 1.402(5) . ? C27 C28 1.364(4) . ? C28 C29 1.411(4) . ? C29 C30 1.409(4) . ? C31 N33 1.506(3) . ? C31 C32 1.520(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 C2 C1 C9 120.8(2) . . ? C2 C1 S1 118.0(2) . . ? C9 C1 S1 121.1(2) . . ? C3 C2 C1 120.8(2) . . ? C2 C3 C4 121.1(3) . . ? C3 C4 C11 122.7(2) . . ? C3 C4 C10 119.1(2) . . ? C11 C4 C10 118.2(3) . . ? C6 C5 C10 119.9(2) . . ? C6 C5 C13 119.6(2) . . ? C10 C5 C13 120.4(2) . . ? C16 C6 C5 119.0(2) . . ? C16 C6 C7 122.4(3) . . ? C5 C6 C7 118.6(2) . . ? C8 C7 C6 121.6(3) . . ? C7 C8 C9 121.6(2) . . ? C1 C9 C10 118.2(2) . . ? C1 C9 C8 124.1(2) . . ? C10 C9 C8 117.8(2) . . ? C9 C10 C5 120.5(2) . . ? C9 C10 C4 120.0(2) . . ? C5 C10 C4 119.5(2) . . ? C12 C11 C4 122.3(3) . . ? C11 C12 C13 121.3(3) . . ? C14 C13 C5 118.9(3) . . ? C14 C13 C12 122.7(2) . . ? C5 C13 C12 118.3(2) . . ? C15 C14 C13 121.0(3) . . ? C14 C15 C16 120.9(3) . . ? C15 C16 C6 120.6(3) . . ? O2 S1 O1 112.85(12) . . ? O2 S1 O3 112.45(12) . . ? O1 S1 O3 112.35(12) . . ? O2 S1 C1 105.46(13) . . ? O1 S1 C1 105.12(12) . . ? O3 S1 C1 107.98(11) . . ? C22 C21 C29 121.2(3) . . ? C21 C22 C23 119.3(3) . . ? C21 C22 C31 119.7(3) . . ? C23 C22 C31 121.0(2) . . ? C24 C23 C22 120.9(3) . . ? C23 C24 C30 121.1(3) . . ? C26 C25 C30 120.0(3) . . ? C25 C26 C27 120.6(3) . . ? C28 C27 C26 120.6(3) . . ? C27 C28 C29 120.3(3) . . ? C30 C29 C28 119.5(3) . . ? C30 C29 C21 118.6(2) . . ? C28 C29 C21 121.9(3) . . ? C29 C30 C24 118.9(2) . . ? C29 C30 C25 119.0(3) . . ? C24 C30 C25 122.0(3) . . ? N33 C31 C22 110.0(2) . . ? N33 C31 C32 109.0(2) . . ? C22 C31 C32 114.1(2) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.470 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.058 #===END