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_4515856
_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