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_4515854
_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         'C25 H26 N2 O2 S2'
_chemical_formula_sum            'C25 H26 N2 O2 S2'
_chemical_formula_weight         450.60
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-05-25
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                112.082(15)
_cell_angle_beta                 94.659(11)
_cell_angle_gamma                115.759(15)
_cell_formula_units_Z            2
_cell_length_a                   10.8541(14)
_cell_length_b                   11.169(2)
_cell_length_c                   12.0753(17)
_cell_measurement_reflns_used    2022
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.9580
_cell_measurement_theta_min      2.1840
_cell_volume                     1168.1(4)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.854
_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    -13.00 106.00   1.00   37.50    --   26.84  77.00   0.00  119
  2  \w    -13.00 106.00   1.00   37.50    --   26.84  77.00 120.00  119
  3  \w    -13.00 106.00   1.00   37.50    --   26.84  77.00-120.00  119
;
_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      0.0198863000
_diffrn_orient_matrix_UB_12      0.0446471000
_diffrn_orient_matrix_UB_13      0.0655078000
_diffrn_orient_matrix_UB_21      0.0400854000
_diffrn_orient_matrix_UB_22      -0.0330839000
_diffrn_orient_matrix_UB_23      0.0096152000
_diffrn_orient_matrix_UB_31      0.0612954000
_diffrn_orient_matrix_UB_32      0.0566133000
_diffrn_orient_matrix_UB_33      -0.0034818000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1146
_diffrn_reflns_av_unetI/netI     0.1650
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6499
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.90
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.850
_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    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triclinic
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.1491
_refine_ls_R_factor_gt           0.0906
_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^)+(0.1111P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1980
_refine_ls_wR_factor_ref         0.2670
_reflns_number_gt                2378
_reflns_number_total             4949
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao8b02116_si_004.cif
_cod_data_source_block           sbl_r_lt_mo
_cod_original_cell_volume        1168.0(3)
_cod_database_code               4515854
_chemical_oxdiff_formula         'C50 H52 N4 O4 S4'
_reflns_odcompleteness_completeness 98.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C17(H17), C4(H4), C2(H2), C10(H10), C13(H13), C14(H14), C23(H23),
 C20(H20), C21(H21), C24(H24), C11(H11)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C31(H31A,H31B,H31C), C16(H16A,H16B,H16C), C29(H29A,H29B,
 H29C)
;
_olex2_date_sample_data_collection 2018-05-24
_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 2.775
_oxdiff_exptl_absorpt_empirical_full_min 0.332