data_2053 _database_code_CSD 189061 _journal_coden_Cambridge 1326 loop_ _publ_author_name 'Tung, Chen-Ho' 'Tang, Xin-Jing' 'Wu, Li-Zhu' 'Zhang, Li-Ping' _publ_contact_author_name 'Prof Chen-Ho Tung' _publ_contact_author_address ; Technical Institute of Physics and Chemistry G516,Technical Institute of Physics ChaoYang 100101 CHINA ; _publ_contact_author_email 'CHTUNG@IPC.AC.CN' _publ_requested_journal 'Phys.Chem.Chem.Phys.' _publ_section_title ; Two-Photon-Pumped Frequency-Upconverted Lasing and Optical Power Limiting Properties of Vinylbenzothiazole-Containing Compounds in Solution ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H21 I N2 O S' _chemical_formula_weight 452.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'I' 'I' -0.4742 1.8119 '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5429(7) _cell_length_b 10.9459(10) _cell_length_c 12.1974(11) _cell_angle_alpha 76.360(2) _cell_angle_beta 78.100(2) _cell_angle_gamma 74.491(2) _cell_volume 931.94(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description sheet _exptl_crystal_colour black _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 1.838 _exptl_absorpt_correction_type 'SADABS -Bruker area detector absorption correc' _exptl_absorpt_correction_T_min 0.748161 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8859 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0788 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 33.44 _reflns_number_total 6492 _reflns_number_gt 3075 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0651P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6492 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0971 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1068 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 0.659 _refine_ls_restrained_S_all 0.659 _refine_ls_shift/su_max 0.520 _refine_ls_shift/su_mean 0.032 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 0.36530(4) 0.78629(2) 0.24936(2) 0.05895(11) Uani 1 1 d . . . S1 S 0.97039(16) 0.53879(9) 0.24018(8) 0.0616(3) Uani 1 1 d . . . O1 O 0.1133(4) 1.0810(3) 0.7118(2) 0.0782(9) Uani 1 1 d . . . H1 H 0.0033 1.1119 0.7057 0.117 Uiso 1 1 calc R . . N1 N 0.9511(4) 0.3134(3) 0.3523(2) 0.0438(6) Uani 1 1 d . . . N2 N 0.3278(4) 0.8374(3) 0.8390(2) 0.0519(7) Uani 1 1 d . . . C1 C 1.0586(4) 0.2930(3) 0.2467(3) 0.0431(7) Uani 1 1 d . . . C2 C 1.1353(5) 0.1755(4) 0.2122(3) 0.0516(9) Uani 1 1 d . . . H2 H 1.1197 0.0982 0.2604 0.062 Uiso 1 1 calc R . . C3 C 1.2355(5) 0.1774(4) 0.1039(3) 0.0576(10) Uani 1 1 d . . . H3 H 1.2882 0.0999 0.0786 0.069 Uiso 1 1 calc R . . C4 C 1.2594(5) 0.2919(4) 0.0320(3) 0.0616(11) Uani 1 1 d . . . H4 H 1.3275 0.2900 -0.0407 0.074 Uiso 1 1 calc R . . C5 C 1.1841(5) 0.4084(4) 0.0661(3) 0.0605(10) Uani 1 1 d . . . H5 H 1.2011 0.4854 0.0178 0.073 Uiso 1 1 calc R . . C6 C 1.0815(5) 0.4078(3) 0.1750(3) 0.0493(8) Uani 1 1 d . . . C7 C 0.9079(6) 0.2081(4) 0.4390(3) 0.0582(10) Uani 1 1 d . . . H7A H 1.0023 0.1779 0.4875 0.087 Uiso 1 1 calc R . . H7B H 0.9030 0.1392 0.4043 0.087 Uiso 1 1 calc R . . H7C H 0.7895 0.2363 0.4837 0.087 Uiso 1 1 calc R . . C8 C 0.8937(5) 0.4377(3) 0.3623(3) 0.0439(7) Uani 1 1 d . . . C9 C 0.7851(5) 0.4838(4) 0.4604(3) 0.0480(8) Uani 1 1 d . . . H9 H 0.7472 0.4243 0.5231 0.058 Uiso 1 1 calc R . . C10 C 0.7350(5) 0.6095(3) 0.4662(3) 0.0461(8) Uani 1 1 d . . . H10 H 0.7739 0.6664 0.4017 0.055 Uiso 1 1 calc R . . C11 C 0.6278(5) 0.6655(3) 0.5611(3) 0.0442(8) Uani 1 1 d . . . C12 C 0.5533(5) 0.5938(3) 0.6616(3) 0.0463(8) Uani 1 1 d . . . H12 H 0.5711 0.5052 0.6676 0.056 Uiso 1 1 calc R . . C13 C 0.4539(5) 0.6494(3) 0.7528(3) 0.0459(8) Uani 1 1 d . . . H13 H 0.4058 0.5980 0.8183 0.055 Uiso 1 1 calc R . . C14 C 0.4243(5) 0.7834(3) 0.7479(3) 0.0433(7) Uani 1 1 d . . . C15 C 0.4973(5) 0.8567(3) 0.6458(3) 0.0483(8) Uani 1 1 d . . . H15 H 0.4786 0.9455 0.6391 0.058 Uiso 1 1 calc R . . C16 C 0.5959(5) 0.7993(3) 0.5559(3) 0.0507(9) Uani 1 1 d . . . H16 H 0.6428 0.8503 0.4897 0.061 Uiso 1 1 calc R . . C17 C 0.2515(6) 0.7583(4) 0.9419(3) 0.0609(10) Uani 1 1 d . . . H17A H 0.1665 0.7175 0.9235 0.091 Uiso 1 1 calc R . . H17B H 0.1868 0.8118 0.9965 0.091 Uiso 1 1 calc R . . H17C H 0.3508 0.6934 0.9737 0.091 Uiso 1 1 calc R . . C18 C 0.3202(5) 0.9703(3) 0.8465(3) 0.0550(9) Uani 1 1 d . . . H18A H 0.4182 1.0008 0.7905 0.066 Uiso 1 1 calc R . . H18B H 0.3442 0.9708 0.9215 0.066 Uiso 1 1 calc R . . C19 C 0.1367(6) 1.0620(4) 0.8269(3) 0.0640(11) Uani 1 1 d . . . H19A H 0.0362 1.0271 0.8762 0.077 Uiso 1 1 calc R . . H19B H 0.1325 1.1441 0.8458 0.077 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 I1 0.06092(18) 0.05634(16) 0.05173(15) -0.00672(10) 0.00164(11) -0.01122(12) S1 0.0722(7) 0.0503(5) 0.0522(5) -0.0122(4) 0.0079(5) -0.0082(5) O1 0.0636(19) 0.094(2) 0.0654(18) -0.0182(16) 0.0001(14) -0.0038(18) N1 0.0419(16) 0.0479(16) 0.0432(15) -0.0177(12) -0.0075(12) -0.0045(13) N2 0.0542(18) 0.0499(17) 0.0522(17) -0.0223(13) 0.0018(14) -0.0096(14) C1 0.0348(17) 0.057(2) 0.0373(16) -0.0161(14) -0.0033(13) -0.0048(15) C2 0.053(2) 0.056(2) 0.0484(19) -0.0194(16) -0.0106(16) -0.0048(18) C3 0.049(2) 0.072(3) 0.054(2) -0.034(2) -0.0101(17) 0.0042(19) C4 0.046(2) 0.088(3) 0.048(2) -0.027(2) 0.0015(16) -0.004(2) C5 0.057(2) 0.070(3) 0.048(2) -0.0113(18) 0.0023(17) -0.012(2) C6 0.043(2) 0.055(2) 0.0468(19) -0.0168(16) -0.0017(15) -0.0042(16) C7 0.059(2) 0.065(2) 0.048(2) -0.0154(17) 0.0015(17) -0.011(2) C8 0.0389(18) 0.0518(19) 0.0417(17) -0.0143(14) -0.0065(14) -0.0066(15) C9 0.047(2) 0.057(2) 0.0397(17) -0.0174(15) -0.0020(14) -0.0090(17) C10 0.0439(19) 0.054(2) 0.0410(17) -0.0161(15) -0.0065(14) -0.0070(16) C11 0.0427(19) 0.0487(19) 0.0440(17) -0.0178(14) -0.0100(14) -0.0050(15) C12 0.053(2) 0.0397(17) 0.0482(18) -0.0165(14) -0.0071(15) -0.0069(15) C13 0.050(2) 0.0459(19) 0.0424(17) -0.0112(14) -0.0038(15) -0.0116(16) C14 0.0394(18) 0.0485(19) 0.0441(18) -0.0159(14) -0.0078(14) -0.0062(15) C15 0.053(2) 0.0385(17) 0.0517(19) -0.0124(14) -0.0064(16) -0.0057(16) C16 0.052(2) 0.048(2) 0.0486(19) -0.0105(15) -0.0013(16) -0.0092(17) C17 0.064(3) 0.069(3) 0.047(2) -0.0215(18) 0.0049(18) -0.011(2) C18 0.054(2) 0.057(2) 0.060(2) -0.0322(18) -0.0049(17) -0.0074(18) C19 0.063(3) 0.063(2) 0.065(2) -0.0292(19) -0.001(2) -0.003(2) _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 S1 C6 1.735(3) . ? S1 C8 1.728(3) . ? O1 C19 1.411(5) . ? N1 C8 1.340(4) . ? N1 C1 1.405(4) . ? N1 C7 1.428(4) . ? N2 C14 1.363(4) . ? N2 C18 1.464(4) . ? N2 C17 1.453(5) . ? C1 C2 1.387(5) . ? C1 C6 1.382(5) . ? C2 C3 1.379(5) . ? C3 C4 1.382(6) . ? C4 C5 1.374(6) . ? C5 C6 1.393(4) . ? C8 C9 1.419(4) . ? C9 C10 1.341(5) . ? C10 C11 1.433(4) . ? C11 C16 1.407(5) . ? C11 C12 1.391(5) . ? C12 C13 1.378(4) . ? C13 C14 1.412(5) . ? C14 C15 1.407(4) . ? C15 C16 1.374(5) . ? C18 C19 1.503(5) . ? 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 S1 C8 91.01(17) . . ? C8 N1 C1 114.4(3) . . ? C8 N1 C7 124.3(3) . . ? C1 N1 C7 121.3(3) . . ? C14 N2 C18 122.7(3) . . ? C14 N2 C17 120.6(3) . . ? C18 N2 C17 116.0(3) . . ? C2 C1 C6 121.2(3) . . ? C2 C1 N1 127.0(3) . . ? C6 C1 N1 111.7(3) . . ? C1 C2 C3 117.6(4) . . ? C4 C3 C2 121.5(3) . . ? C3 C4 C5 121.1(3) . . ? C4 C5 C6 118.0(4) . . ? C1 C6 C5 120.7(3) . . ? C1 C6 S1 111.2(2) . . ? C5 C6 S1 128.1(3) . . ? N1 C8 C9 125.4(3) . . ? N1 C8 S1 111.7(2) . . ? C9 C8 S1 122.9(3) . . ? C10 C9 C8 122.6(3) . . ? C9 C10 C11 127.0(3) . . ? C16 C11 C12 116.7(3) . . ? C16 C11 C10 120.0(3) . . ? C12 C11 C10 123.3(3) . . ? C13 C12 C11 122.3(3) . . ? C12 C13 C14 120.8(3) . . ? N2 C14 C15 122.4(3) . . ? N2 C14 C13 120.5(3) . . ? C15 C14 C13 117.1(3) . . ? C16 C15 C14 121.1(3) . . ? C11 C16 C15 121.9(3) . . ? N2 C18 C19 113.6(3) . . ? O1 C19 C18 110.1(3) . . ? _diffrn_measured_fraction_theta_max 0.894 _diffrn_reflns_theta_full 33.44 _diffrn_measured_fraction_theta_full 0.894 _refine_diff_density_max 0.988 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.087