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_7158673
_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, C18 H20 F6 N3 O, 0.5(C H4 O)'
_chemical_formula_sum            'C18.5 H22 F12 N3 O1.5 P'
_chemical_formula_weight         569.36
_chemical_name_systematic        FY-005_3
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   55.7279(19)
_cell_length_b                   8.6632(2)
_cell_length_c                   9.3599(3)
_cell_measurement_reflns_used    6613
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.1500
_cell_measurement_theta_min      4.9700
_cell_volume                     4518.8(2)
_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 1.000
_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    -62.00   1.00   0.50   16.15    --  -48.70  71.00 -38.00  126
  2  \w   -167.00 -98.00   0.50   64.61    --  -97.00 -92.00 -51.00  138
  3  \w   -170.00 -84.00   0.50   64.61    --  -97.00 -71.00-169.00  172
  4  \w    -73.00 -47.00   0.50   64.61    --  -97.00  61.00-171.00   52
  5  \w   -112.00 -47.00   0.50   16.15    --  -48.70 -37.00-150.00  130
  6  \w    -16.00  19.00   0.50   16.15    --   48.70 -19.00 150.00   70
  7  \w    -68.00 -27.00   0.50   64.61    --  -97.00  57.00 150.00   82
  8  \w    -56.00 -31.00   0.50   64.61    --  -97.00  57.00 -90.00   50
  9  \w    -67.00 -39.00   0.50   64.61    --  -97.00  57.00 -30.00   56
 10  \w     36.00  61.00   0.50   64.61    --  108.36 -57.00 120.00   50
 11  \w     37.00  63.00   0.50   64.61    --  108.36 -57.00-150.00   52
 12  \w     36.00  61.00   0.50   64.61    --  108.36 -57.00   0.00   50
 13  \w     36.00  64.00   0.50   64.61    --  108.36 -57.00 -30.00   56
 14  \w     39.00  64.00   0.50   64.61    --  108.36 -57.00  90.00   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      -0.0319051000
_diffrn_orient_matrix_UB_12      -0.0618851000
_diffrn_orient_matrix_UB_13      0.0253671000
_diffrn_orient_matrix_UB_21      -0.1283008000
_diffrn_orient_matrix_UB_22      0.1105372000
_diffrn_orient_matrix_UB_23      0.0019781000
_diffrn_orient_matrix_UB_31      -0.0980576000
_diffrn_orient_matrix_UB_32      -0.1247132000
_diffrn_orient_matrix_UB_33      -0.0108269000
_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  0.0705
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       68
_diffrn_reflns_limit_h_min       -66
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18212
_diffrn_reflns_point_group_measured_fraction_full 0.790
_diffrn_reflns_point_group_measured_fraction_max 0.733
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.592
_diffrn_reflns_theta_min         3.172
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    2.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84620
_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    1.674
_exptl_crystal_description       plate
_exptl_crystal_F_000             2312
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.112
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.879
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Flack x determined using 1334 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     669
_refine_ls_number_reflns         7027
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0834
_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^)+(0.1570P)^2^+3.5513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2318
_refine_ls_wR_factor_ref         0.2608
_reflns_Friedel_coverage         0.454
_reflns_Friedel_fraction_full    0.550
_reflns_Friedel_fraction_max     0.488
_reflns_number_gt                4788
_reflns_number_total             7027
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00546h2.cif
_cod_data_source_block           3
_cod_original_formula_sum        'C18.50 H22 F12 N3 O1.50 P'
_cod_database_code               7158673
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N F O P'
_diffrn_oxdiff_digest_frames
;
016d02e860545949cc9eb1435685fa7609011345fd3
;
_diffrn_oxdiff_digest_hkl
;
0172fc4071096c621887e357564cdde121c4fa
;
_reflns_odcompleteness_completeness 99.96
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N00W-C01X \\sim N00W-C1
 with sigma of 0.02
 N00W-C2 \\sim N00W-C2A
 with sigma of 0.02
 C01X-C5 \\sim C1-C5A
 with sigma of 0.02
 O1-C4 \\sim O1A-C4A
 with sigma of 0.02
 O1-C5 \\sim O1A-C5A
 with sigma of 0.02
 C2-C4 \\sim C2A-C4A
 with sigma of 0.02
 N00W-C4 \\sim N00W-C4A
 with sigma of 0.04
 N00W-C5 \\sim N00W-C5A
 with sigma of 0.04
 C01X-O1 \\sim C1-O1A
 with sigma of 0.04
 O1-C2 \\sim O1A-C2A
 with sigma of 0.04
 C4-C5 \\sim C4A-C5A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C01X)
Uanis(C2) = Uanis(C2A)
Uanis(C4) = Uanis(C4A)
Uanis(C5) = Uanis(C5A)
Uanis(O1) = Uanis(O1A)
4. Others
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(O1A)=Sof(C5A)=
 Sof(H5AA)=Sof(H5AB)=Sof(C1)=Sof(H1A)=Sof(H1B)=1-FVAR(1)
 Sof(C01X)=Sof(H01H)=Sof(H01K)=Sof(O1)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C4)=
 Sof(H4A)=Sof(H4B)=Sof(C5)=Sof(H5A)=Sof(H5B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C01D(H01M,H01N), C01H(H01A,H01B), C01L(H01P,H01Q), C01M(H01R,H01S), C01R(H01C,
 H01D), C01S(H01X,H01Y), C01T(H01Z,H), C01U(H01,HA), C01X(H01H,H01K), C2(H2A,
 H2B), C4(H4A,H4B), C5(H5A,H5B), C2A(H2AA,H2AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB),
  C1(H1A,H1B)
5.b Aromatic/amide H refined with riding coordinates:
 N00M(H00M), C010(H010), N012(H012), C016(H016), C019(H019), C01C(H01L),
 C01F(H01O), C01I(H01I), C01J(H01J), C01N(H01T)
5.c Idealised Me refined as rotating group:
 C01O(H01U,H01V,H01W), C01V(H01E,H01F,H01G), C01Y(H2,HB,HC)
5.d Idealised tetrahedral OH refined as rotating group:
 O01B(H1)
;
_olex2_submission_original_sample_id FY-005_3
_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 2.037
_oxdiff_exptl_absorpt_empirical_full_min 0.629