#------------------------------------------------------------------------------ #$Date: 2019-11-10 18:52:32 +0200 (Sun, 10 Nov 2019) $ #$Revision: 225956 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/51/58/4515856.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4515856 loop_ _publ_author_name 'Gupta, Abhishek Kumar' 'Kumar, Ashwani' 'Singh, Ranjit' 'Devi, Manisha' 'Dhir, Abhimanew' 'Pradeep, Chullikkattil P.' _publ_section_title ; Facile Synthesis of an Organic Solid State Near-Infrared-Emitter with Large Stokes Shift via Excited-State Intramolecular Proton Transfer. ; _journal_issue 10 _journal_name_full 'ACS omega' _journal_page_first 14341 _journal_page_last 14348 _journal_paper_doi 10.1021/acsomega.8b02116 _journal_volume 3 _journal_year 2018 _chemical_absolute_configuration ad _chemical_formula_moiety 'C15 H15 N O2 S' _chemical_formula_sum 'C15 H15 N O2 S' _chemical_formula_weight 273.34 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2017-05-29 _audit_creation_method ; Olex2 1.2-ac21 (compiled 2015.09.16 svn.r134, GUI svn.r4998) ; _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.2088(3) _cell_length_b 9.2720(6) _cell_length_c 28.3737(17) _cell_measurement_reflns_used 1283 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 65.7880 _cell_measurement_theta_min 3.1100 _cell_volume 1370.34(14) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 15.9974 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames -------------------------------------------------------------------------- 1 \w -13.00 41.00 1.00 1.00 -- 25.69 57.00 60.00 54 2 \w 43.00 100.00 1.00 1.00 -- 25.69 57.00 60.00 57 3 \w -7.00 106.00 1.00 10.00 -- 66.85 -45.00-120.00 113 4 \w 89.00 115.00 1.00 10.00 -- 66.85-111.00-180.00 26 5 \w 12.00 83.00 1.00 10.00 -- 66.85-111.00-180.00 71 6 \w 139.00 167.00 1.00 65.00 -- 108.00 138.00-120.00 28 7 \w 108.00 157.00 1.00 65.00 -- 108.00 104.00-120.00 49 8 \w 102.00 127.00 1.00 65.00 -- 108.00 138.00-120.00 25 9 \w 102.00 169.00 1.00 65.00 -- 108.00 104.00 150.00 67 10 \w 104.00 172.00 1.00 65.00 -- 108.00 104.00 -90.00 68 11 \w 83.00 153.00 1.00 65.00 -- 108.00 -43.00-180.00 70 12 \w 28.00 74.00 1.00 65.00 -- 108.00 -43.00-180.00 46 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0255048000 _diffrn_orient_matrix_UB_12 0.0209870000 _diffrn_orient_matrix_UB_13 0.0536815000 _diffrn_orient_matrix_UB_21 -0.2782808000 _diffrn_orient_matrix_UB_22 -0.0558119000 _diffrn_orient_matrix_UB_23 -0.0021410000 _diffrn_orient_matrix_UB_31 0.0967506000 _diffrn_orient_matrix_UB_32 -0.1550527000 _diffrn_orient_matrix_UB_33 0.0079793000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_unetI/netI 0.0433 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 2564 _diffrn_reflns_theta_full 66.72 _diffrn_reflns_theta_max 66.72 _diffrn_reflns_theta_min 5.02 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.075 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.568 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_description orthorhombic _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.264 _exptl_crystal_size_mid 0.076 _exptl_crystal_size_min 0.054 _refine_diff_density_max 0.316 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.070 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 175 _refine_ls_number_reflns 1901 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0644 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1438P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1756 _refine_ls_wR_factor_ref 0.1816 _reflns_number_gt 1749 _reflns_number_total 1901 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ao8b02116_si_002.cif _cod_data_source_block sbl_148_rt_cu _cod_original_cell_volume 1370.33(15) _cod_database_code 4515856 _chemical_oxdiff_formula 'C60 H60 N4 O8 S4' _reflns_odcompleteness_completeness 97.85 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Aromatic/amide H refined with riding coordinates: C4(H4), C8(H8), C6(H6), C14(H14), C11(H11), C12(H12), C3(H3), C7(H7) 2.b Idealised Me refined as rotating group: C15(H15A,H15B,H15C), C1(H1A,H1B,H1C) 2.c Idealised tetrahedral OH refined as rotating group: O1(H1) ; _olex2_date_sample_data_collection 2016-12-07 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 2.147 _oxdiff_exptl_absorpt_empirical_full_min 0.493 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' 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_calc_flag _atom_site_refinement_flags_posn S1 S -0.1129(2) 0.27170(13) 0.12349(3) 0.0738(4) Uani 1 d . O2 O 0.6142(7) 0.5327(3) 0.49982(10) 0.0763(8) Uani 1 d . C15 C 0.3964(13) 0.6229(6) 0.49859(18) 0.0881(14) Uani 1 d . H15A H 0.4193 0.6955 0.4748 0.132 Uiso 1 calc GR H15B H 0.3746 0.6683 0.5287 0.132 Uiso 1 calc GR H15C H 0.2471 0.5664 0.4914 0.132 Uiso 1 calc GR C4 C 0.1045(9) 0.3739(4) 0.25681(13) 0.0629(9) Uani 1 d . H4 H 0.0591 0.4391 0.2803 0.075 Uiso 1 calc R N1 N 0.4506(6) 0.2711(3) 0.30651(10) 0.0567(7) Uani 1 d . C9 C 0.5635(6) 0.3470(4) 0.38438(12) 0.0536(7) Uani 1 d . C2 C 0.0360(6) 0.2781(4) 0.17920(12) 0.0527(7) Uani 1 d . C8 C 0.4045(7) 0.3523(4) 0.34239(12) 0.0534(7) Uani 1 d . H8 H 0.2662 0.4158 0.3414 0.064 Uiso 1 calc R C1 C -0.3307(10) 0.4222(5) 0.12312(17) 0.0786(12) Uani 1 d . H1A H -0.4024 0.4332 0.0922 0.118 Uiso 1 calc GR H1B H -0.2397 0.5084 0.1316 0.118 Uiso 1 calc GR H1C H -0.4662 0.4053 0.1454 0.118 Uiso 1 calc GR C5 C 0.3023(6) 0.2781(3) 0.26500(11) 0.0500(7) Uani 1 d . C6 C 0.3651(8) 0.1817(4) 0.22934(14) 0.0608(8) Uani 1 d . H6 H 0.4972 0.1158 0.2340 0.073 Uiso 1 calc R C10 C 0.7679(7) 0.2515(4) 0.38890(13) 0.0601(8) Uani 1 d . C14 C 0.5078(7) 0.4430(4) 0.42151(13) 0.0563(8) Uani 1 d . H14 H 0.3715 0.5072 0.4187 0.068 Uiso 1 calc R C11 C 0.9079(8) 0.2497(5) 0.43065(16) 0.0719(10) Uani 1 d . H11 H 1.0405 0.1836 0.4345 0.086 Uiso 1 calc R C13 C 0.6531(7) 0.4423(4) 0.46180(13) 0.0589(8) Uani 1 d . C12 C 0.8515(8) 0.3452(5) 0.46638(14) 0.0674(10) Uani 1 d . H12 H 0.9486 0.3441 0.4939 0.081 Uiso 1 calc R O1 O 0.8322(7) 0.1580(4) 0.35406(12) 0.0818(9) Uani 1 d . H1 H 0.7355 0.1693 0.3316 0.123 Uiso 1 calc GR C3 C -0.0275(8) 0.3754(5) 0.21465(14) 0.0628(9) Uani 1 d . H3 H -0.1592 0.4415 0.2099 0.075 Uiso 1 calc R C7 C 0.2341(9) 0.1823(4) 0.18703(13) 0.0640(9) Uani 1 d . H7 H 0.2800 0.1173 0.1635 0.077 Uiso 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 S1 0.0881(6) 0.0782(6) 0.0552(5) -0.0146(4) -0.0066(4) -0.0104(6) O2 0.092(2) 0.0744(16) 0.0623(15) 0.0000(13) -0.0233(15) 0.0056(18) C15 0.102(3) 0.085(3) 0.077(3) -0.019(2) -0.023(3) 0.015(3) C4 0.0709(19) 0.0636(19) 0.0541(16) -0.0144(15) 0.0009(16) 0.009(2) N1 0.0592(14) 0.0535(14) 0.0573(15) 0.0056(12) 0.0038(11) 0.0022(14) C9 0.0531(15) 0.0508(15) 0.0568(16) 0.0151(14) -0.0013(13) -0.0054(15) C2 0.0603(16) 0.0487(15) 0.0492(15) -0.0036(13) 0.0080(13) -0.0155(16) C8 0.0519(14) 0.0501(15) 0.0583(17) 0.0088(13) -0.0002(14) 0.0030(16) C1 0.081(2) 0.082(3) 0.072(2) 0.001(2) -0.016(2) -0.018(2) C5 0.0543(14) 0.0454(15) 0.0502(14) 0.0009(12) 0.0092(13) -0.0042(14) C6 0.0651(18) 0.0485(15) 0.0688(19) -0.0018(14) 0.0081(17) 0.0119(17) C10 0.0564(16) 0.0631(18) 0.0608(17) 0.0141(15) 0.0051(14) 0.0031(18) C14 0.0572(15) 0.0516(16) 0.0600(18) 0.0125(14) -0.0054(14) -0.0025(16) C11 0.0602(17) 0.080(2) 0.075(2) 0.020(2) -0.0041(17) 0.010(2) C13 0.0625(18) 0.0570(16) 0.0571(17) 0.0160(14) -0.0086(15) -0.0146(17) C12 0.0628(19) 0.080(2) 0.0593(19) 0.0210(18) -0.0078(15) -0.006(2) O1 0.0757(17) 0.091(2) 0.0784(18) -0.0016(16) -0.0012(14) 0.0286(18) C3 0.0653(18) 0.0634(19) 0.0596(17) -0.0090(16) -0.0063(15) 0.0129(19) C7 0.081(2) 0.0518(17) 0.0591(17) -0.0107(14) 0.0131(18) 0.0015(19) 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' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 6 -4 0.0472 -3 -1 12 0.0837 0 -5 11 0.0200 2 -3 -13 0.0821 -3 -2 0 0.1100 2 1 15 0.0710 0 -5 -11 0.0302 0 2 17 0.0187 0 5 10 0.0348 0 0 -18 0.0328 3 0 -3 0.1296 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 S1 C1 104.87(19) C13 O2 C15 117.3(3) O2 C15 H15A 109.5 O2 C15 H15B 109.5 O2 C15 H15C 109.5 H15A C15 H15B 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C5 C4 H4 119.2 C3 C4 H4 119.2 C3 C4 C5 121.6(3) C8 N1 C5 122.0(3) C10 C9 C8 122.3(3) C10 C9 C14 119.4(3) C14 C9 C8 118.3(3) C3 C2 S1 124.5(3) C7 C2 S1 116.9(3) C7 C2 C3 118.6(3) N1 C8 C9 121.4(3) N1 C8 H8 119.3 C9 C8 H8 119.3 S1 C1 H1A 109.5 S1 C1 H1B 109.5 S1 C1 H1C 109.5 H1A C1 H1B 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 C4 C5 N1 125.4(3) C4 C5 C6 117.9(3) C6 C5 N1 116.7(3) C5 C6 H6 119.5 C7 C6 C5 120.9(3) C7 C6 H6 119.5 C9 C10 C11 119.2(4) O1 C10 C9 121.9(3) O1 C10 C11 118.9(3) C9 C14 H14 119.8 C13 C14 C9 120.4(3) C13 C14 H14 119.8 C10 C11 H11 119.8 C12 C11 C10 120.5(4) C12 C11 H11 119.8 C14 C13 O2 124.6(4) C14 C13 C12 119.8(4) C12 C13 O2 115.7(3) C11 C12 H12 119.6 C13 C12 C11 120.7(3) C13 C12 H12 119.6 C10 O1 H1 109.5 C4 C3 C2 120.1(3) C4 C3 H3 119.9 C2 C3 H3 119.9 C2 C7 C6 120.8(3) C2 C7 H7 119.6 C6 C7 H7 119.6 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C2 1.762(3) S1 C1 1.798(6) O2 C15 1.409(7) O2 C13 1.381(5) C15 H15A 0.9600 C15 H15B 0.9600 C15 H15C 0.9600 C4 H4 0.9300 C4 C5 1.380(5) C4 C3 1.380(6) N1 C8 1.289(5) N1 C5 1.410(4) C9 C8 1.452(5) C9 C10 1.391(5) C9 C14 1.409(5) C2 C3 1.391(5) C2 C7 1.380(6) C8 H8 0.9300 C1 H1A 0.9600 C1 H1B 0.9600 C1 H1C 0.9600 C5 C6 1.390(5) C6 H6 0.9300 C6 C7 1.381(6) C10 C11 1.391(6) C10 O1 1.357(5) C14 H14 0.9300 C14 C13 1.371(5) C11 H11 0.9300 C11 C12 1.378(7) C13 C12 1.377(6) C12 H12 0.9300 O1 H1 0.8200 C3 H3 0.9300 C7 H7 0.9300 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 O1 H1 N1 0.82 1.90 2.621(4) 146.8 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion S1 C2 C3 C4 -178.5(3) S1 C2 C7 C6 178.7(3) O2 C13 C12 C11 180.0(4) C15 O2 C13 C14 5.8(6) C15 O2 C13 C12 -173.4(4) C4 C5 C6 C7 0.2(5) N1 C5 C6 C7 -178.7(3) C9 C10 C11 C12 -2.5(6) C9 C14 C13 O2 179.5(3) C9 C14 C13 C12 -1.3(5) C8 N1 C5 C4 3.3(5) C8 N1 C5 C6 -177.9(3) C8 C9 C10 C11 -178.3(3) C8 C9 C10 O1 0.5(5) C8 C9 C14 C13 -179.8(3) C1 S1 C2 C3 4.5(4) C1 S1 C2 C7 -173.4(3) C5 C4 C3 C2 0.5(6) C5 N1 C8 C9 -178.1(3) C5 C6 C7 C2 -0.5(6) C10 C9 C8 N1 -2.2(5) C10 C9 C14 C13 -0.1(5) C10 C11 C12 C13 1.2(6) C14 C9 C8 N1 177.5(3) C14 C9 C10 C11 2.0(5) C14 C9 C10 O1 -179.2(4) C14 C13 C12 C11 0.8(6) O1 C10 C11 C12 178.6(4) C3 C4 C5 N1 178.6(4) C3 C4 C5 C6 -0.2(6) C3 C2 C7 C6 0.7(5) C7 C2 C3 C4 -0.7(6) loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.0013 6.0086 -4.0044 -0.0888 -0.3264 -0.9637 -3.0008 -1.0118 11.9759 0.6982 0.8659 -0.0379 -0.0001 -5.0143 11.0026 0.4854 0.2563 0.8653 2.0025 -2.9904 -12.9803 -0.8106 -0.3626 0.5538 -2.9987 -2.0013 -0.0216 0.0333 0.9462 0.0200 1.9970 0.9866 15.0127 0.7757 -0.6429 0.1600 0.0033 -4.9937 -10.9944 -0.6951 0.3013 0.6869 -0.0032 1.9857 16.9961 0.9541 -0.1463 -0.1726 -0.0031 4.9947 9.9945 0.6414 -0.2993 -0.6950 0.0027 0.0168 -17.9976 -0.9659 0.0368 -0.1460 2.9998 0.0025 -2.9763 -0.2362 -0.8286 0.2661