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_7158671
_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         'C17 H17 F6 N3 O'
_chemical_formula_sum            'C17 H17 F6 N3 O'
_chemical_formula_weight         393.33
_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                 91.6470(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.55670(10)
_cell_length_b                   18.5529(3)
_cell_length_c                   9.70230(10)
_cell_measurement_reflns_used    8096
_cell_measurement_temperature    93
_cell_measurement_theta_max      73.6940
_cell_measurement_theta_min      4.6180
_cell_volume                     1719.55(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.34a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.34a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.34a (Rigaku OD, 2019)'
_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                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.927
_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    143.00 175.00   0.50    0.10    --  110.12 125.00 -90.00   64
  2  \w     97.00 123.00   0.50    0.10    --  110.12 125.00 -90.00   52
  3  \w     85.00 111.00   0.50    0.05    --   40.95 137.00  47.00   52
  4  \w    -40.00   5.00   0.50    0.05    --   40.95 -19.00  60.00   90
  5  \w    -41.00  23.00   0.50    0.05    --   40.95 -19.00 -30.00  128
  6  \w    -18.00  20.00   0.50    0.05    --   40.95 -19.00-150.00   76
  7  \w     45.00  70.00   0.50    0.10    --  110.12 -77.00-180.00   50
  8  \w     40.00  65.00   0.50    0.10    --  110.12 -61.00  30.00   50
  9  \w     38.00  63.00   0.50    0.10    --  110.12 -61.00 120.00   50
 10  \w     69.00  94.00   0.50    0.10    --  110.12-132.00 161.00   50
 11  \w     62.00 104.00   0.50    0.05    --   40.95-132.00 161.00   84
 12  \w     53.00  78.00   0.50    0.05    --   40.95-137.00 -15.00   50
 13  \w     53.00  78.00   0.50    0.10    --  110.12-137.00 -15.00   50
 14  \w    -68.00 -38.00   0.50    0.05    --  -40.95 137.00  47.00   60
 15  \w   -120.00 -87.00   0.50    0.10    --  -97.00 137.00  47.00   66
 16  \w    -73.00 -48.00   0.50    0.05    --  -40.95 132.00-129.00   50
 17  \w   -108.00 -19.00   0.50    0.10    --  -97.00 109.00-142.12  178
 18  \w    -96.00 -71.00   0.50    0.10    --  -97.00 132.00-129.00   50
 19  \w    -95.00 -64.00   0.50    0.10    --  -97.00  77.00-120.00   62
 20  \w    -76.00 -51.00   0.50    0.10    --  -97.00  61.00 -90.00   50
 21  \w    -50.00 -25.00   0.50    0.10    --  -97.00  77.00-120.00   50
 22  \w    -42.00 -17.00   0.50    0.10    --  -97.00  30.00 -60.00   50
 23  \w    -47.00 -20.00   0.50    0.10    --  -97.00  45.00   0.00   54
 24  \w    -40.00 -15.00   0.50    0.10    --  -97.00  30.00  30.00   50
 25  \w    -55.00 -29.00   0.50    0.10    --  -97.00  45.00  60.00   52
 26  \w    -39.00 -14.00   0.50    0.10    --  -97.00  30.00  60.00   50
 27  \w    -49.00 -19.00   0.50    0.10    --  -97.00  45.00  90.00   60
 28  \w    -41.00 -16.00   0.50    0.10    --  -97.00  30.00 120.00   50
 29  \w    -40.00 -14.00   0.50    0.10    --  -97.00  30.00  90.00   52
 30  \w    -34.00  40.00   0.50    0.05    --  -40.95  19.00 120.00  148
 31  \w   -147.00 -74.00   0.50    0.10    --  -97.00-137.00 -15.00  146
 32  \w   -111.00 -79.00   0.50    0.10    --  -97.00-132.00 161.00   64
 33  \w   -167.00-115.00   0.50    0.10    --  -97.00-132.00 161.00  104
 34  \w   -173.00 -88.00   0.50    0.10    --  -97.00 -94.00-120.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0109026000
_diffrn_orient_matrix_UB_12      -0.0799617000
_diffrn_orient_matrix_UB_13      0.0421598000
_diffrn_orient_matrix_UB_21      -0.0479218000
_diffrn_orient_matrix_UB_22      -0.0225612000
_diffrn_orient_matrix_UB_23      -0.1467411000
_diffrn_orient_matrix_UB_31      0.1535071000
_diffrn_orient_matrix_UB_32      -0.0011871000
_diffrn_orient_matrix_UB_33      -0.0437907000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11771
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.125
_diffrn_reflns_theta_min         4.629
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.245
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.34a (Rigaku Oxford Diffraction, 2019)
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    1.519
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_preparation       'ACN, rt,Luminescent'
_exptl_crystal_recrystallization_method ACN
_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0673P)^2^+0.4163P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2879
_reflns_number_total             3237
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00546h2.cif
_cod_data_source_block           exp_251
_cod_database_code               7158671
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N F O'
_chemical_oxdiff_usercomment     'ACN, rt'
_shelx_estimated_absorpt_t_max   0.886
_shelx_estimated_absorpt_t_min   0.806
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C13(H13a,H13b), C18(H18a,H18b), C15(H15a,H15b), C16(H16a,
 H16b), C19(H19a,H19b)
2.b Aromatic/amide H refined with riding coordinates:
 N11(H11), C3(H3), C5(H5), 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 1.511
_oxdiff_exptl_absorpt_empirical_full_min 0.645