4,5,5-Trimethyl-2,5-dihydrofuran-Based Electron-Withdrawing Groups for NIR-Emitting Push-Pull Dipolar Fluorophores.
Rémond, Maxime; Zheng, Zheng; Jeanneau, Erwann; Andraud, Chantal; Bretonnière, Yann; Redon, Sébastien; The Journal of organic chemistry 84 (2019) 9965–9974; doi:10.1021/acs.joc.9b01120

data_4034017
_publ_section_title
;
 4,5,5-Trimethyl-2,5-dihydrofuran-Based Electron-Withdrawing Groups for
 NIR-Emitting Push-Pull Dipolar Fluorophores.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9965
_journal_page_last               9974
_journal_paper_doi               10.1021/acs.joc.9b01120
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C46 H39 N3 O S'
_chemical_formula_sum            'C46 H39 N3 O S'
_chemical_formula_weight         681.90
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 105.731(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.113(3)
_cell_length_b                   9.141(8)
_cell_length_c                   19.164(2)
_cell_measurement_reflns_used    6241
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      27.5810
_cell_measurement_theta_min      2.9920
_cell_volume                     3729(3)
_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    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.071
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33835
_diffrn_reflns_theta_full        26.212
_diffrn_reflns_theta_max         29.661
_diffrn_reflns_theta_min         2.770
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.091
_refine_diff_density_max         1.87
_refine_diff_density_min         -1.39
_refine_ls_extinction_coef       260(20)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0599
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         9261
_refine_ls_number_restraints     76
_refine_ls_R_factor_all          0.1486
_refine_ls_R_factor_gt           0.0988
_refine_ls_shift/su_max          0.0007650
_refine_ls_shift/su_mean         0.0000323
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 194. 252. 82.9 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1661
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1661
_reflns_limit_h_max              27
_reflns_limit_h_min              -29
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                5723
_reflns_number_total             9283
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.10
_oxford_diffrn_Wilson_scale      0.41
_oxford_refine_ls_r_factor_ref   0.1486
_oxford_refine_ls_scale          1.557(10)
_oxford_reflns_number_all        9261
_cod_data_source_file            jo9b01120_si_007.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4034017
_oxdiff_exptl_absorpt_empirical_full_min 0.936
_oxdiff_exptl_absorpt_empirical_full_max 1.103
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)