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_1557107
_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         'I, C16 H19 N2'
_chemical_formula_sum            'C16 H19 I N2'
_chemical_formula_weight         366.23
_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
_audit_creation_date             2018-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-03-20 deposited with the CCDC.	2019-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.1584(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.29025(14)
_cell_length_b                   7.62301(17)
_cell_length_c                   32.0065(7)
_cell_measurement_reflns_used    4226
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.6210
_cell_measurement_theta_min      5.5010
_cell_volume                     1534.73(6)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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    -77.00 -43.00   1.00    0.10    --  -48.45  96.00 161.00   34
  2  \w     10.00  39.00   1.00    0.10    --   48.45 -96.00  53.00   29
  3  \w   -157.00-127.00   1.00    0.15    --  -86.25 -96.00  53.00   30
  4  \w    -72.00 -47.00   1.00    0.15    --  -86.25  96.00 161.00   25
  5  \w   -106.00 -81.00   1.00    0.15    --  -86.25 -96.00  53.00   25
  6  \w     83.00 108.00   1.00    0.15    --  107.75 -96.00  53.00   25
  7  \w    -39.00   4.00   1.00    0.10    --  -48.45  96.00 161.00   43
  8  \w   -117.00 -70.00   1.00    0.10    --  -48.45-125.00   0.00   47
  9  \w   -120.00 -70.00   1.00    0.10    --  -48.45-125.00-150.00   50
 10  \w    -20.00  63.00   1.00    0.10    --   48.45 -57.00 120.00   83
 11  \w   -146.00 -75.00   1.00    0.15    --  -86.25 -37.00  90.00   71
 12  \w     99.00 176.00   1.00    0.15    --  107.75  37.00 -30.00   77
 13  \w     35.00 123.00   1.00    0.15    --  107.75 -57.00  60.00   88
 14  \w     40.00 108.00   1.00    0.15    --  107.75 -99.00   0.00   68
 15  \w    101.00 172.00   1.00    0.15    --  107.75  37.00 -60.00   71
 16  \w    106.00 178.00   1.00    0.15    --  107.75  96.00 161.00   72
;
_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      0.0522888000
_diffrn_orient_matrix_UB_12      -0.0573383000
_diffrn_orient_matrix_UB_13      0.0450075000
_diffrn_orient_matrix_UB_21      -0.0723001000
_diffrn_orient_matrix_UB_22      0.1805880000
_diffrn_orient_matrix_UB_23      0.0162616000
_diffrn_orient_matrix_UB_31      -0.2281314000
_diffrn_orient_matrix_UB_32      -0.0704085000
_diffrn_orient_matrix_UB_33      0.0049941000
_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  0.0586
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            8481
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         5.529
_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    16.289
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.30d (Rigaku Oxford Diffraction, 2017)
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    1.585
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.868
_refine_diff_density_min         -1.056
_refine_diff_density_rms         0.199
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0961P)^2^+3.2391P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2365
_reflns_number_total             2724
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05875c2.cif
_cod_data_source_block           180724a
_cod_depositor_comments
'Adding full bibliography for 1557107--1557109.cif.'
_cod_database_code               1557107
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CNI
_diffrn_oxdiff_ac3_digest_frames
;
01dcfa186d9e0d4bb967f0eac23c18e09100838de40
;
_diffrn_oxdiff_ac3_digest_hkl
;
0144990f283d2158ef80d86697db5716fd6e10
;
_reflns_odcompleteness_completeness 99.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              45063
_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 36.422
_oxdiff_exptl_absorpt_empirical_full_min 0.325