Acid Responsiveness of Emissive Morpholinyl Aminoquinolines and Their Use for Cell Fluorescence Imaging
Fukumoto, Yuri; Umeno, Tomohiro; Kuramochi, Hina; Hamada, Koichi; Matsumoto, Shota; Suzuki, Noriko; Usui, Kazuteru; Mizutani, Akihiro; Karasawa, Satoru; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00546H

data_7158674
_publ_section_title
;
 Acid Responsiveness of Emissive Morpholinyl Aminoquinolines and Their Use
 for Cell Fluorescence Imaging
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00546H
_journal_year                    2022
_chemical_formula_moiety         'C23 H28 F6 N4 O2'
_chemical_formula_sum            'C23 H28 F6 N4 O2'
_chemical_formula_weight         506.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-27
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-04-09 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.732(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5656(2)
_cell_length_b                   18.4733(5)
_cell_length_c                   22.5869(7)
_cell_measurement_reflns_used    5890
_cell_measurement_temperature    93
_cell_measurement_theta_max      73.8650
_cell_measurement_theta_min      2.3850
_cell_volume                     2322.08(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.948
_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     89.00 115.00   0.50    0.84    --  110.12  45.00   0.00   52
  2  \w    143.00 169.00   0.50    0.84    --  110.12  45.00   0.00   52
  3  \w     93.00 173.00   0.50    0.84    --  110.12  51.00 -69.00  160
  4  \w     84.00 116.00   0.50    0.84    --  110.12  61.00-120.00   64
  5  \w    119.00 168.00   0.50    0.84    --  110.12  61.00-120.00   98
  6  \w     36.00  85.00   0.50    0.84    --  110.12 -77.00  30.00   98
  7  \w     64.00  95.00   0.50    0.84    --  110.12 -77.00  90.00   62
  8  \w     36.00  81.00   0.50    0.84    --  110.12 -77.00 150.00   90
  9  \w     35.00  60.00   0.50    0.84    --  110.12 -61.00 150.00   50
 10  \w    -16.00   9.00   0.50    0.21    --   40.70 -51.00 144.00   50
 11  \w     35.00  60.00   0.50    0.84    --  110.12 -61.00   0.00   50
 12  \w     35.00  60.00   0.50    0.84    --  110.12 -61.00 -90.00   50
 13  \w     35.00  60.00   0.50    0.84    --  110.12 -61.00-180.00   50
 14  \w    -71.00 -21.00   0.50    0.84    --  -97.00  61.00 120.00  100
 15  \w    -55.00 -29.00   0.50    0.84    --  -97.00  45.00 120.00   52
 16  \w    -52.00 -21.00   0.50    0.84    --  -97.00  45.00  30.00   62
 17  \w    -50.00 -22.00   0.50    0.84    --  -97.00  45.00  90.00   56
 18  \w    -41.00 -15.00   0.50    0.84    --  -97.00  30.00  60.00   52
 19  \w    -39.00 -14.00   0.50    0.84    --  -97.00  30.00  90.00   50
 20  \w    -51.00 -19.00   0.50    0.84    --  -97.00  51.00 -69.00   64
 21  \w    -42.00 -17.00   0.50    0.84    --  -97.00  30.00 -90.00   50
 22  \w    -53.00 -28.00   0.50    0.84    --  -97.00  45.00-120.00   50
 23  \w    -63.00  37.00   0.50    0.21    --  -40.70  51.00 -69.00  200
 24  \w    -42.00 -17.00   0.50    0.84    --  -97.00  30.00  30.00   50
 25  \w   -157.00-131.00   0.50    0.84    --  -97.00 -51.00 144.00   52
 26  \w   -147.00 -87.00   0.50    0.84    --  -97.00 -94.00 -90.00  120
 27  \w   -124.00 -53.00   0.50    0.21    --  -40.70-179.00 -60.00  142
 28  \w   -110.00 -26.00   0.50    0.21    --  -40.70 -51.00 144.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-Custom'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0142477000
_diffrn_orient_matrix_UB_12      -0.0414146000
_diffrn_orient_matrix_UB_13      -0.0591046000
_diffrn_orient_matrix_UB_21      0.2521443000
_diffrn_orient_matrix_UB_22      -0.0316235000
_diffrn_orient_matrix_UB_23      0.0118683000
_diffrn_orient_matrix_UB_31      -0.1132318000
_diffrn_orient_matrix_UB_32      -0.0651690000
_diffrn_orient_matrix_UB_33      0.0318641000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13461
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.309
_diffrn_reflns_theta_min         3.091
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    1.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.63a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 'MeOH (rt, slow evaporation)'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0681
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0876P)^2^+2.7037P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1824
_refine_ls_wR_factor_ref         0.1877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3946
_reflns_number_total             4463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00546h2.cif
_cod_data_source_block           exp_252
_cod_database_code               7158674
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N F O'
_chemical_oxdiff_usercomment     'MeOH, rt'
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.827
_diffrn_oxdiff_digest_frames
;
0199841bf011db67878d82abe1d3451e600219436b2
;
_diffrn_oxdiff_digest_hkl
;
0142ffb8157265b8a0b3ddf01eaa2fe991c897
;
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C14(H14a,H14b), C12(H12a,H12b), C15(H15a,H15b), C21(H21a,
 H21b), C17(H17a,H17b), C20(H20a,H20b), C18(H18a,H18b), C27(H27a,H27b),
 C23(H23a,H23b), C26(H26a,H26b), C24(H24a,H24b)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C6(H6), C9(H9)
;
_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 1.615
_oxdiff_exptl_absorpt_empirical_full_min 0.687