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_7158672
_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         'F6 P, C19 H22 F6 N3 O'
_chemical_formula_sum            'C19 H22 F12 N3 O P'
_chemical_formula_weight         567.36
_chemical_name_systematic        FY-005_7
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-04-09 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                81.551(3)
_cell_angle_beta                 85.313(3)
_cell_angle_gamma                80.624(3)
_cell_formula_units_Z            2
_cell_length_a                   6.1777(2)
_cell_length_b                   8.8010(3)
_cell_length_c                   22.3052(8)
_cell_measurement_reflns_used    5758
_cell_measurement_temperature    93
_cell_measurement_theta_max      75.1090
_cell_measurement_theta_min      4.0180
_cell_volume                     1181.47(7)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (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 0.998
_diffrn_measured_fraction_theta_max 0.929
_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   -119.00 -69.00   0.50    5.53    --  -48.82-152.00   9.00  100
  2  \w    -93.00 -57.00   0.50    5.53    --  -48.82 121.00-107.00   72
  3  \w    -98.00 -73.00   0.50    5.53    --  -48.82 152.00  51.00   50
  4  \w     71.00 101.00   0.50    5.53    --   48.82-152.00   9.00   60
  5  \w     31.00  57.00   0.50    5.53    --   48.82-121.00 168.00   52
  6  \w     61.00 105.00   0.50    5.53    --   48.82 152.00  51.00   88
  7  \w   -138.00-113.00   0.50   22.14    --  -97.00-152.00   9.00   50
  8  \w   -107.00 -54.00   0.50   22.14    --  -97.00 121.00-107.00  106
  9  \w   -160.00 -86.00   0.50   22.14    --  -97.00-121.00 168.00  148
 10  \w   -129.00 -44.00   0.50   22.14    --  -97.00 152.00  51.00  170
 11  \w    104.00 130.00   0.50   22.14    --  108.36-152.00   9.00   52
 12  \w     49.00  74.00   0.50   22.14    --  108.36-121.00 168.00   50
 13  \w    118.00 171.00   0.50   22.14    --  108.36 121.00-107.00  106
 14  \w     37.00  63.00   0.50   22.14    --  108.36-152.00   9.00   52
 15  \w    -26.00  27.00   0.50    5.53    --  -48.82  19.00 -90.00  106
 16  \w    -24.00  37.00   0.50    5.53    --   48.82 -37.00-150.00  122
 17  \w    -25.00  23.00   0.50    5.53    --   48.82 -19.00-120.00   96
 18  \w    -19.00  37.00   0.50    5.53    --   48.82 -37.00 -60.00  112
 19  \w     80.00 122.00   0.50    5.53    --   48.82 125.00 -30.00   84
 20  \w    -20.00   5.00   0.50    5.53    --   48.82 -19.00 -90.00   50
 21  \w   -115.00 -87.00   0.50   22.14    --  -97.00 -19.00 150.00   56
 22  \w    -57.00 -24.00   0.50   22.14    --  -97.00  77.00  90.00   66
 23  \w    -66.00 -25.00   0.50   22.14    --  -97.00  57.00-120.00   82
 24  \w   -171.00-119.00   0.50   22.14    --  -97.00 -19.00 150.00  104
 25  \w   -157.00 -91.00   0.50   22.14    --  -97.00-125.00 -60.00  132
 26  \w    -67.00 -24.00   0.50   22.14    --  -97.00  57.00  30.00   86
 27  \w   -169.00 -82.00   0.50   22.14    --  -97.00 -57.00-120.00  174
 28  \w   -168.00-143.00   0.50   22.14    --  -97.00 -57.00   0.00   50
 29  \w   -123.00 -97.00   0.50   22.14    --  -97.00 -99.00-150.00   52
 30  \w    -66.00 -28.00   0.50   22.14    --  -97.00  57.00-150.00   76
 31  \w   -119.00 -88.00   0.50   22.14    --  -97.00 -57.00   0.00   62
 32  \w   -169.00-126.00   0.50   22.14    --  -97.00 -99.00-150.00   86
 33  \w   -141.00 -92.00   0.50   22.14    --  -97.00 -99.00 120.00   98
 34  \w     80.00 105.00   0.50   22.14    --  108.36 -99.00  30.00   50
 35  \w     75.00 102.00   0.50   22.14    --  108.36 -77.00-180.00   54
 36  \w     39.00  68.00   0.50   22.14    --  108.36 -77.00-180.00   58
 37  \w     39.00  64.00   0.50   22.14    --  108.36 -99.00 -60.00   50
 38  \w     50.00 111.00   0.50   22.14    --  108.36-125.00  60.00  122
 39  \w     38.00  63.00   0.50   22.14    --  108.36 -57.00-150.00   50
 40  \w     71.00 106.00   0.50   22.14    --  108.36 -99.00 -60.00   70
 41  \w     36.00  61.00   0.50   22.14    --  108.36 -57.00  30.00   50
 42  \w     52.00 100.00   0.50   22.14    --  108.36 -99.00 -30.00   96
 43  \w     77.00 109.00   0.50   22.14    --  108.36-125.00-120.00   64
 44  \w    102.00 127.00   0.50   22.14    --  108.36 152.00  51.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  Rigaku_Synergy-Custom_007
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1010640000
_diffrn_orient_matrix_UB_12      0.0772889000
_diffrn_orient_matrix_UB_13      -0.0599133000
_diffrn_orient_matrix_UB_21      -0.0968103000
_diffrn_orient_matrix_UB_22      -0.1084848000
_diffrn_orient_matrix_UB_23      -0.0353041000
_diffrn_orient_matrix_UB_31      -0.2109999000
_diffrn_orient_matrix_UB_32      0.1196869000
_diffrn_orient_matrix_UB_33      -0.0075307000
_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  0.0461
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15135
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.410
_diffrn_reflns_theta_min         4.014
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    2.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70371
_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    1.595
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.064
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0708
_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^)+(0.1240P)^2^+0.7401P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1978
_refine_ls_wR_factor_ref         0.2158
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3267
_reflns_number_total             4672
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00546h2.cif
_cod_data_source_block           7
_cod_database_code               7158672
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N F O P'
_diffrn_oxdiff_digest_frames
;
0188f2617783b5f69858f9667d1c604cb603564cb46
;
_diffrn_oxdiff_digest_hkl
;
01e9e0b9a63e7649da2f43a2b25378cf2a0212
;
_reflns_odcompleteness_completeness 99.93
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C26(H26A,H26B), C19(H19A,H19B), C25(H25A,H25B), C22(H22A,
 H22B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C9(H9), C15(H15)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C21(H21A,H21B,H21C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_original_sample_id FY-005_7
_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 1.575
_oxdiff_exptl_absorpt_empirical_full_min 0.630