A side-chain engineering strategy for constructing fluorescent dyes with direct and ultrafast self-delivery to living cells
Guo, Lifang; Li, Chuanya; Shang, Hai; Zhang, Ruoyao; Li, Xuechen; Lu, Qing; Cheng, Xiao; Liu, Zhiqiang; Sun, Jing Zhi; Yu, Xiaoqiang; Chemical Science 11 (2020) 661–670; doi:10.1039/C9SC05875C

data_1557108
_publ_section_title
;
 A side-chain engineering strategy for constructing fluorescent dyes with
 direct and ultrafast self-delivery to living cells
;
_journal_issue                   3
_journal_name_full               'Chemical Science'
_journal_page_first              661
_journal_page_last               670
_journal_paper_doi               10.1039/C9SC05875C
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         '3(I), 2(C21 H29 N2), C22 H29 N, 2(O)'
_chemical_formula_sum            'C64 H87 I3 N5 O2'
_chemical_formula_weight         1339.08
_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             2018-08-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2019-03-20 deposited with the CCDC.	2019-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                85.945(4)
_cell_angle_beta                 73.880(4)
_cell_angle_gamma                62.636(5)
_cell_formula_units_Z            2
_cell_length_a                   14.6729(7)
_cell_length_b                   15.6807(7)
_cell_length_c                   16.4518(7)
_cell_measurement_reflns_used    8417
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      76.3580
_cell_measurement_theta_min      3.4770
_cell_volume                     3222.3(3)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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     45.00  78.00   1.00    0.90    --   48.45 -95.00  50.00   33
  2  \w     35.00  95.00   1.00    0.90    --   48.45-125.00 -60.00   60
  3  \w     42.00 106.00   1.00    9.00    --  107.75 -95.00  50.00   64
  4  \w     37.00 115.00   1.00    9.00    --  107.75-125.00  60.00   78
  5  \w     37.00 109.00   1.00    9.00    --  107.75 -99.00 150.00   72
  6  \w     36.00 131.00   1.00    9.00    --  107.75 -77.00 150.00   95
  7  \w     35.00 109.00   1.00    9.00    --  107.75 -99.00 -60.00   74
  8  \w     95.00 177.00   1.00    9.00    --  107.75  37.00 -90.00   82
  9  \w     95.00 178.00   1.00    9.00    --  107.75  37.00-120.00   83
 10  \w     85.00 178.00   1.00    9.00    --  107.75  77.00 -60.00   93
 11  \w     92.00 178.00   1.00    9.00    --  107.75 125.00  90.00   86
 12  \w    102.00 152.00   1.00    9.00    --  107.75  95.00 160.00   50
 13  \w     -5.00  44.00   1.00    0.90    --   48.45 -95.00  50.00   49
 14  \w    -61.00  20.00   1.00    0.90    --  -48.45  37.00  90.00   81
 15  \w    -74.00  24.00   1.00    0.90    --  -48.45  95.00 160.00   98
 16  \w    -80.00 -54.00   1.00    9.00    --  -86.25  95.00 160.00   26
 17  \w    -84.00 -40.00   1.00    0.90    --  -48.45 -57.00  90.00   44
 18  \w   -120.00 -86.00   1.00    0.90    --  -48.45 -57.00  90.00   34
 19  \w   -146.00 -81.00   1.00    9.00    --  -86.25 -95.00  50.00   65
 20  \w   -159.00 -71.00   1.00    9.00    --  -86.25 -57.00  60.00   88
 21  \w   -119.00 -70.00   1.00    0.90    --  -48.45-125.00-180.00   49
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1051365000
_diffrn_orient_matrix_UB_12      0.0426868000
_diffrn_orient_matrix_UB_13      -0.0254652000
_diffrn_orient_matrix_UB_21      -0.0610166000
_diffrn_orient_matrix_UB_22      0.0557320000
_diffrn_orient_matrix_UB_23      0.0873251000
_diffrn_orient_matrix_UB_31      0.0189417000
_diffrn_orient_matrix_UB_32      0.0858148000
_diffrn_orient_matrix_UB_33      -0.0356286000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30522
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.530
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    11.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             1362
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.452
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     694
_refine_ls_number_reflns         11369
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0496
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1579
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8495
_reflns_number_total             11369
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05875c2.cif
_cod_data_source_block           180802e
_cod_depositor_comments
'Adding full bibliography for 1557107--1557109.cif.'
_cod_database_code               1557108
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CN
_reflns_odcompleteness_completeness 99.05
_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. Uiso/Uaniso restraints and constraints
C00W \\sim C01A \\sim C00L \\sim C015 \\sim C011 \\sim N005: within 1.7A with
sigma of 0.004 and sigma for terminal atoms of 0.008
C00Z \\sim C00H \\sim C00O \\sim C00I \\sim C009 \\sim C00E: within 1.7A with
sigma of 0.004 and sigma for terminal atoms of 0.008
C01Y \\sim C01R \\sim C01P \\sim C01W \\sim C01Z \\sim C00X: within 1.7A with
sigma of 0.004 and sigma for terminal atoms of 0.008
3. Others
 Fixed Sof: I002(0.4) I1(0.4) I0AA(0.6) I1AA(0.6)
4.a Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00C(H00D,H00E), C00G(H00G,H00H), C00J(H00J,H00K), C00K(H00L,
 H00M), C00M(H00T,H00U), C00Q(H00V,H00W), C00V(H00,H), C016(H01J,H01K),
 C01B(H01M,H01N), C01F(H0AA,HA), C01H(H1AA,HB), C01O(H4AA,HC), C01V(H9AA,HF),
 C021(H02D,H02E)
4.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00E(H00F), C00I(H00I), C00L(H00Q), C00N(H00N), C00O(H00O),
 C00P(H00P), C00R(H00R), C00S(H00S), C00U(H00X), C00Y(H00Y), C00Z(H00Z),
 C011(H011), C013(H013), C015(H015), C017(H017), C019(H019), C01A(H01L),
 C01C(H01), C01I(H2AA), C01J(H3AA), C01L(H01X), C01M(H01Y), C01N(H01Z),
 C01Q(H5AA), C01R(H6AA), C01T(H7AA), C01W(H0BA), C01Y(H1BA), C01Z(H2BA)
4.c Idealised Me refined as rotating group:
 C012(H01A,H01B,H01C), C018(H01D,H01E,H01F), C01D(H01O,H01P,H01Q), C01E(H01R,
 H01S,H01T), C01G(H01G,H01H,H01I), C01K(H01U,H01V,H01W), C01U(H8AA,HD,HE),
 C020(H02A,H02B,H02C), C022(H02F,H02G,H02H)
;
_shelx_res_checksum              55428
_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 3.133
_oxdiff_exptl_absorpt_empirical_full_min 0.478