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_4034016
_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_absolute_configuration ad
_chemical_formula_moiety         'C20 H15 N5 O S, 2(C H4 O)'
_chemical_formula_sum            'C22 H23 N5 O3 S'
_chemical_formula_weight         437.51
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   55.259(2)
_cell_length_b                   21.9278(9)
_cell_length_c                   7.1347(3)
_cell_measurement_reflns_used    15189
_cell_measurement_temperature    150
_cell_measurement_theta_max      67.1160
_cell_measurement_theta_min      4.0100
_cell_volume                     8645.2(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.074
_diffrn_reflns_limit_h_max       58
_diffrn_reflns_limit_h_min       -65
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            38356
_diffrn_reflns_theta_full        66.305
_diffrn_reflns_theta_max         68.592
_diffrn_reflns_theta_min         3.199
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.618
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3680
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.458
_exptl_crystal_size_min          0.216
_refine_diff_density_max         0.51
_refine_diff_density_min         -0.36
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 1739 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.164(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0196
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.0024594
_refine_ls_shift/su_mean         0.0001037
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.10P)^2^ +16.86P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1287
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1271
_reflns_limit_h_max              65
_reflns_limit_h_min              0
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              -8
_reflns_number_gt                3838
_reflns_number_total             3868
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.12
_oxford_diffrn_Wilson_scale      0.66
_oxford_refine_ls_r_factor_ref   0.0426
_oxford_refine_ls_scale          1.294(8)
_oxford_reflns_number_all        3868
_cod_data_source_file            jo9b01120_si_003.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'F d d 2 '
_cod_database_code               4034016
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_hooft_y                  0.153(8)
_oxford_bijvoet_difference       0.164(3)
_oxford_refined_flack_x          0.197(12)