# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name parksy@snu.ac.kr _publ_contact_author_email Yoon, _publ_section_title ; Polymorphic and Mechanochromic Luminescence Modulation in the Highly Emissive Dicyanodistyrylbenzene Crystal: Secondary Bonding Interaction in Molecular Stacking Assembly ; loop_ _publ_author_name 'Seong-Jun Yoon' 'SooYoung Park' # Attachment '- a-bdcs1.cif' data_a-bdcs1 _database_code_depnum_ccdc_archive 'CCDC 799014' #TrackingRef '- a-bdcs1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H16 N2' _chemical_formula_weight 332.39 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 6.8239(4) _cell_length_b 7.2324(3) _cell_length_c 35.2082(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1737.64(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2070 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 24.29 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type 'Multi-scan SADABS' _exptl_absorpt_correction_T_min 0.9757 _exptl_absorpt_correction_T_max 0.9944 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8242 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.16 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1989 _reflns_number_gt 1471 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0788P)^2^+0.1972P] 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 1989 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1538 _refine_ls_wR_factor_gt 0.1319 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _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 N1 N 0.0349(2) 0.1272(2) 0.09156(4) 0.0440(5) Uani 1 1 d . . . C1 C 0.3189(2) 0.0752(2) 0.00829(4) 0.0305(4) Uani 1 1 d . . . H1A H 0.1937 0.1259 0.0138 0.037 Uiso 1 1 calc R . . C2 C 0.4538(2) 0.0496(2) 0.03752(4) 0.0263(4) Uani 1 1 d . . . C3 C 0.6349(2) -0.0279(2) 0.02867(4) 0.0308(4) Uani 1 1 d . . . H3A H 0.7280 -0.0484 0.0483 0.037 Uiso 1 1 calc R . . C4 C 0.4056(2) 0.1041(2) 0.07711(4) 0.0255(4) Uani 1 1 d . . . C5 C 0.1992(3) 0.1158(2) 0.08591(4) 0.0289(4) Uani 1 1 d . . . C6 C 0.5415(2) 0.1488(2) 0.10319(5) 0.0289(4) Uani 1 1 d . . . H6A H 0.6732 0.1466 0.0944 0.035 Uiso 1 1 calc R . . C7 C 0.5161(2) 0.2006(2) 0.14324(4) 0.0265(4) Uani 1 1 d . . . C8 C 0.3666(3) 0.1329(2) 0.16644(5) 0.0312(4) Uani 1 1 d . . . H8A H 0.2721 0.0497 0.1564 0.037 Uiso 1 1 calc R . . C9 C 0.3564(3) 0.1875(3) 0.20415(5) 0.0363(5) Uani 1 1 d . . . H9A H 0.2548 0.1407 0.2199 0.044 Uiso 1 1 calc R . . C10 C 0.4923(3) 0.3089(2) 0.21908(5) 0.0373(5) Uani 1 1 d . . . H10A H 0.4835 0.3465 0.2449 0.045 Uiso 1 1 calc R . . C11 C 0.6410(3) 0.3754(2) 0.19623(5) 0.0389(5) Uani 1 1 d . . . H11A H 0.7340 0.4601 0.2062 0.047 Uiso 1 1 calc R . . C12 C 0.6547(3) 0.3190(2) 0.15895(5) 0.0343(5) Uani 1 1 d . . . H12A H 0.7604 0.3617 0.1437 0.041 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 N1 0.0292(9) 0.0663(12) 0.0366(9) 0.0021(8) 0.0000(7) 0.0018(8) C1 0.0255(9) 0.0375(10) 0.0285(9) -0.0030(7) 0.0004(7) 0.0040(8) C2 0.0271(9) 0.0276(9) 0.0241(8) 0.0004(6) 0.0003(6) -0.0004(7) C3 0.0257(9) 0.0385(10) 0.0282(9) 0.0002(7) -0.0037(7) 0.0032(8) C4 0.0244(8) 0.0259(8) 0.0261(8) 0.0001(6) 0.0015(6) 0.0012(7) C5 0.0279(10) 0.0338(10) 0.0250(8) -0.0012(7) -0.0005(7) 0.0002(7) C6 0.0256(9) 0.0332(9) 0.0279(9) 0.0001(7) 0.0022(7) -0.0006(7) C7 0.0263(9) 0.0283(9) 0.0250(8) 0.0004(6) -0.0015(6) 0.0025(7) C8 0.0306(10) 0.0332(9) 0.0299(9) 0.0003(7) -0.0003(7) -0.0029(8) C9 0.0367(10) 0.0432(11) 0.0289(9) 0.0018(7) 0.0058(8) 0.0006(8) C10 0.0480(12) 0.0399(10) 0.0239(8) -0.0034(7) -0.0031(8) 0.0080(9) C11 0.0454(12) 0.0384(11) 0.0328(10) -0.0028(7) -0.0086(8) -0.0060(9) C12 0.0338(10) 0.0407(11) 0.0285(9) 0.0006(7) -0.0010(7) -0.0080(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 N1 C5 1.142(2) . ? C1 C3 1.382(2) 5_655 ? C1 C2 1.393(2) . ? C2 C3 1.392(2) . ? C2 C4 1.486(2) . ? C3 C1 1.382(2) 5_655 ? C4 C6 1.344(2) . ? C4 C5 1.445(2) . ? C6 C7 1.469(2) . ? C7 C12 1.391(2) . ? C7 C8 1.395(2) . ? C8 C9 1.387(2) . ? C9 C10 1.381(2) . ? C10 C11 1.381(3) . ? C11 C12 1.378(2) . ? 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 C3 C1 C2 120.79(16) 5_655 . ? C3 C2 C1 118.35(14) . . ? C3 C2 C4 120.87(14) . . ? C1 C2 C4 120.78(15) . . ? C1 C3 C2 120.85(15) 5_655 . ? C6 C4 C5 120.79(15) . . ? C6 C4 C2 123.51(15) . . ? C5 C4 C2 115.63(14) . . ? N1 C5 C4 177.52(17) . . ? C4 C6 C7 129.45(15) . . ? C12 C7 C8 118.72(15) . . ? C12 C7 C6 117.28(14) . . ? C8 C7 C6 123.95(15) . . ? C9 C8 C7 119.81(16) . . ? C10 C9 C8 120.78(17) . . ? C9 C10 C11 119.52(16) . . ? C12 C11 C10 120.11(17) . . ? C11 C12 C7 121.00(16) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.179 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.051