Facile Synthesis of an Organic Solid State Near-Infrared-Emitter with Large Stokes Shift via Excited-State Intramolecular Proton Transfer.
Gupta, Abhishek Kumar; Kumar, Ashwani; Singh, Ranjit; Devi, Manisha; Dhir, Abhimanew; Pradeep, Chullikkattil P.; ACS omega 3 (2018) 14341–14348; doi:10.1021/acsomega.8b02116

data_4515855
_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_formula_moiety         'C23 H22 N2 O2 S2'
_chemical_formula_sum            'C23 H22 N2 O2 S2'
_chemical_formula_weight         422.54
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                93.055(3)
_cell_angle_beta                 107.510(4)
_cell_angle_gamma                106.789(4)
_cell_formula_units_Z            4
_cell_length_a                   10.0414(4)
_cell_length_b                   15.0433(6)
_cell_length_c                   15.5315(6)
_cell_measurement_reflns_used    6400
_cell_measurement_temperature    300
_cell_measurement_theta_max      66.7130
_cell_measurement_theta_min      3.0120
_cell_volume                     2116.64(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43i (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43i (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43i (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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      300
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9987
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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     -6.00  88.00   1.00    1.00    --   25.44  57.00  30.00   94
  2  \w    101.00 132.00   1.00    2.00    --   66.72  63.00 -90.00   31
  3  \w    100.00 135.00   1.00    2.00    --   66.72 111.00-150.00   35
  4  \w    108.00 145.00   1.00    2.00    --   66.72 111.00-120.00   37
  5  \w     96.00 175.00   1.00   10.00    --  108.00  32.00-150.00   79
  6  \w    119.00 175.00   1.00   10.00    --  108.00 138.00  30.00   56
  7  \w    110.00 175.00   1.00   10.00    --  108.00  65.00 150.00   65
  8  \w    112.00 178.00   1.00   10.00    --  108.00 104.00 120.00   66
  9  \w     75.00 145.00   1.00    2.00    --   66.72  12.00 -90.00   70
 10  \w     82.00 164.00   1.00   10.00    --  108.00  65.00 -90.00   82
 11  \w     65.00 138.00   1.00    2.00    --   66.72 178.00 -90.00   73
 12  \w     67.00 172.00   1.00   10.00    --  108.00  77.00 -60.00  105
 13  \w     69.00 178.00   1.00   10.00    --  108.00  54.00-120.00  109
 14  \w    117.00 143.00   1.00   10.00    --  108.00 -65.00  60.00   26
 15  \w     66.00 112.00   1.00   10.00    --  108.00-104.00  90.00   46
 16  \w     61.00 138.00   1.00   10.00    --  108.00 -65.00 120.00   77
 17  \w     73.00  99.00   1.00   10.00    --  108.00  65.00 150.00   26
 18  \w     31.00 101.00   1.00   10.00    --  108.00 -65.00  60.00   70
 19  \w     37.00 118.00   1.00   10.00    --  108.00-117.00 -29.91   81
 20  \w     73.00 109.00   1.00   10.00    --  108.00-104.00-180.00   36
 21  \w     28.00  57.00   1.00   10.00    --  108.00-104.00-180.00   29
 22  \w     19.00  83.00   1.00    2.00    --   66.72-111.00-120.00   64
 23  \w     28.00  93.00   1.00   10.00    --  108.00-104.00   0.00   65
 24  \w     23.00  56.00   1.00   10.00    --  108.00-104.00  90.00   33
 25  \w     23.00 101.00   1.00   10.00    --  108.00-104.00  60.00   78
 26  \w      7.00 116.00   1.00    2.00    --   66.72 -38.00 -90.00  109
 27  \w     41.00  67.00   1.00    2.00    --   66.72  63.00 -90.00   26
 28  \w     -9.00  95.00   1.00    1.00    --   25.44  57.00 -90.00  104
 29  \w    -10.00 100.00   1.00    1.00    --   25.44  57.00 150.00  110
 30  \w      1.00 117.00   1.00    2.00    --   66.72 -91.00 -60.00  116
 31  \w    -14.00  72.00   1.00    2.00    --   66.72  12.00 -90.00   86
;
_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      0.0460423000
_diffrn_orient_matrix_UB_12      0.0932978000
_diffrn_orient_matrix_UB_13      -0.0365299000
_diffrn_orient_matrix_UB_21      -0.1399184000
_diffrn_orient_matrix_UB_22      0.0196063000
_diffrn_orient_matrix_UB_23      0.0052470000
_diffrn_orient_matrix_UB_31      0.0844936000
_diffrn_orient_matrix_UB_32      0.0512802000
_diffrn_orient_matrix_UB_33      0.0985754000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12596
_diffrn_reflns_theta_full        66.97
_diffrn_reflns_theta_max         66.97
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.452
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.43i (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_colour            'metallic dark red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triclinic
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     531
_refine_ls_number_reflns         7383
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0668P)^2^+1.0115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1652
_reflns_number_gt                6129
_reflns_number_total             7383
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao8b02116_si_003.cif
_cod_data_source_block           sbl_126_rt_cu
_cod_depositor_comments
;

2020-04-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2116.64(15)
_cod_original_formula_moiety     '2(C23 H22 N2 O2 S2)'
_cod_original_formula_sum        'C46 H44 N4 O4 S4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     845.09
_cod_database_code               4515855
_chemical_oxdiff_formula         'C92 H88 N8 O8 S8'
_reflns_odcompleteness_completeness 97.75
_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:
 C26(H26), C6(H6), C25(H25), C28(H28), C29(H29), C7(H7), C4(H4), C37(H37),
 C15(H15), C21(H21), C8(H8), C20(H20), C3(H3), C39(H39), C34(H34), C30(H30),
 C12(H12), C40(H40), C43(H43), C17(H17), C10(H10), C42(H42), C32(H32), C18(H18)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C1(H1A,H1B,H1C), C46(H46A,H46B,H46C), C45(H45A,H45B,
 H45C), C44(H44A,H44B,H44C), C22(H22A,H22B,H22C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4A)
;
_olex2_date_sample_data_collection 2016-04-11
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.842
_oxdiff_exptl_absorpt_empirical_full_min 0.211