Experimental and theoretical comprehension of ESIPT fluorophores based on a 2-(2'-hydroxyphenyl)-3,3'-dimethylindole (HDMI) scaffold.
Stoerkler, Timothée; Ulrich, Gilles; Retailleau, Pascal; Laurent, Adèle D; Jacquemin, Denis; Massue, Julien; Chemical science 15 (2024) 7206–7218; doi:10.1039/d4sc01937g

data_1571448
_publ_section_title
;
 Experimental and theoretical comprehension of ESIPT fluorophores based on
 a 2-(2'-hydroxyphenyl)-3,3'-dimethylindole (HDMI) scaffold.
;
_journal_issue                   19
_journal_name_full               'Chemical science'
_journal_page_first              7206
_journal_page_last               7218
_journal_paper_doi               10.1039/d4sc01937g
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C26 H21 N3 O'
_chemical_formula_sum            'C26 H21 N3 O'
_chemical_formula_weight         391.476
_chemical_name_systematic
"'2,4-dibromo-6-(3,3-dimethyl-3H-indol-2-yl)phenol'"
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2023-04-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-02 deposited with the CCDC.	2024-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                70.6975(19)
_cell_angle_beta                 89.7069(17)
_cell_angle_gamma                85.8279(17)
_cell_formula_units_Z            2
_cell_length_a                   8.50238(18)
_cell_length_b                   10.0282(2)
_cell_length_c                   12.6916(3)
_cell_measurement_reflns_used    20125
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      32.8260
_cell_measurement_theta_min      2.9800
_cell_volume                     1018.39(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9987
_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    -20.00  99.00   0.50    3.00    --    9.20  59.00  20.35  238
  2  \w    -20.00  99.00   0.50    3.00    --    9.20  57.00  60.00  238
  3  \w    -20.00  99.00   0.50    3.00    --    9.20  57.00-180.00  238
  4  \w    -22.00  99.00   0.50    3.00    --    9.20  38.00 -90.00  242
  5  \w    -20.00  99.00   0.50    3.00    --    9.20  57.00-120.00  238
  6  \w    -20.00  99.00   0.50    3.00    --    9.20  57.00   0.00  238
  7  \w    -20.00  99.00   0.50    3.00    --    9.20  57.00 120.00  238
  8  \w    -20.00  99.00   0.50    3.00    --    9.20  59.00 -45.09  238
  9  \w    -41.00 -16.00   0.50    3.00    --   -9.80  38.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0470734000
_diffrn_orient_matrix_UB_12      -0.0467861000
_diffrn_orient_matrix_UB_13      0.0396933000
_diffrn_orient_matrix_UB_21      0.0640642000
_diffrn_orient_matrix_UB_22      -0.0191423000
_diffrn_orient_matrix_UB_23      0.0389852000
_diffrn_orient_matrix_UB_31      -0.0260626000
_diffrn_orient_matrix_UB_32      0.0556158000
_diffrn_orient_matrix_UB_33      0.0203120000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.9984
_diffrn_reflns_Laue_measured_fraction_max 0.9987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39300
_diffrn_reflns_point_group_measured_fraction_full 0.9984
_diffrn_reflns_point_group_measured_fraction_max 0.9987
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         3.11
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.554
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
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            yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       prism
_exptl_crystal_F_000             412.242
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane / methanol'
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.173
_refine_diff_density_max         0.1111
_refine_diff_density_min         -0.1250
_refine_diff_density_rms         0.0212
_refine_ls_d_res_high            0.7401
_refine_ls_d_res_low             6.5572
_refine_ls_extinction_coef       0.0077(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0715
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     461
_refine_ls_number_reflns         5266
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.0635
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0153
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0127P)^2^+0.0096P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0325
_refine_ls_wR_factor_ref         0.0336
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                4604
_reflns_number_total             5266
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4sc01937g2.cif
_cod_data_source_block           TS727
_cod_depositor_comments
'Adding full bibliography for 1571447--1571448.cif.'
_cod_database_code               1571448
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     '173 K'
_olex2_refinement_description
;
1. Rigid body (RIGU) restrains
 C15, C16, C17, N2, C18, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C20, C21, C22, N3, C23, C24
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_olex2_refine_details
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      cc-pVTZ
   CHARGE:         0
   MULTIPLICITY:   1
   SOLVATION:      CH2CL2
   DATE:           2023-04-28_12-27-25
;
_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 1.286
_oxdiff_exptl_absorpt_empirical_full_min 0.801