Unprecedented perspectives on the application of CinNapht fluorophores provided by a "late-stage" functionalization strategy.
Tacke, Eléonore; Hoang, Minh-Duc; Tatoueix, Kevin; Keromnes, Benoît; Van Eslande, Elsa; Durand, Philippe; Pieters, Gregory; Chevalier, Arnaud; Chemical science 14 (2023) 6000–6010; doi:10.1039/d3sc01365k

data_1569188
_publ_section_title
;
 Unprecedented perspectives on the application of CinNapht fluorophores
 provided by a "late-stage" functionalization strategy.
;
_journal_issue                   22
_journal_name_full               'Chemical science'
_journal_page_first              6000
_journal_page_last               6010
_journal_paper_doi               10.1039/d3sc01365k
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C22 H16 F N3 O2'
_chemical_formula_sum            'C22 H16 F N3 O2'
_chemical_formula_weight         373.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-11-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-11-21 deposited with the CCDC.	2023-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.507(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8187(4)
_cell_length_b                   15.7239(18)
_cell_length_c                   22.4752(16)
_cell_measurement_reflns_used    2755
_cell_measurement_temperature    273
_cell_measurement_theta_max      62.30
_cell_measurement_theta_min      3.40
_cell_volume                     1702.3(3)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.0
_diffrn_detector                 'Rapid 2'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device
'four-circle partial \c goniometer diffractometer'
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  'Confocal Osmic mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11107
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        65.085
_diffrn_reflns_theta_max         65.085
_diffrn_reflns_theta_min         3.431
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku micromax 007 1.2kW'
_exptl_absorpt_coefficient_mu    0.849
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Reqab (Higashi-Rigaku, 1998)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             776
_exptl_crystal_preparation       'slow evaporation'
_exptl_crystal_recrystallization_method 'heptane/ethyl acetate'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2878
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.2014
_refine_ls_R_factor_gt           0.0934
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2397
_refine_ls_wR_factor_ref         0.3593
_reflns_Friedel_coverage         0.000
_reflns_number_gt                895
_reflns_number_total             2878
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01365k2.cif
_cod_data_source_block           compound-4
_cod_depositor_comments          'Adding full bibliography for 1569188.cif.'
_cod_database_code               1569188
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.676
_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:
 C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C14(H14), C18(H18), C16(H16), C11(H11), C17(H17), C12(H12)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              98251
_olex2_exptl_crystal_mounting_method cryoloop
_olex2_submission_special_instructions 'No special instructions were received'