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_1557109
_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, C17 H18 N2'
_chemical_formula_sum            'C17 H18 I N2'
_chemical_formula_weight         377.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-08-09
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9063(2)
_cell_length_b                   7.9318(2)
_cell_length_c                   30.1570(6)
_cell_measurement_reflns_used    7084
_cell_measurement_temperature    173.00(2)
_cell_measurement_theta_max      76.2590
_cell_measurement_theta_min      5.7640
_cell_volume                     1651.98(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.998
_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    -66.00  19.00   1.00    0.10    --  -48.45  64.00 123.00   85
  2  \w    -93.00 -31.00   1.00    0.10    --  -48.45 -64.00 -13.00   62
  3  \w     52.00  77.00   1.00    0.10    --   48.45  64.00 123.00   25
  4  \w      7.00  34.00   1.00    0.10    --   48.45 -64.00 -13.00   27
  5  \w    -48.00 -22.00   1.00    0.40    --  -86.25  64.00 123.00   26
  6  \w   -159.00-122.00   1.00    0.40    --  -86.25 -64.00 -13.00   37
  7  \w     41.00 124.00   1.00    0.40    --  107.75 -64.00 -13.00   83
  8  \w     90.00 178.00   1.00    0.40    --  107.75  64.00 123.00   88
  9  \w   -120.00 -76.00   1.00    0.10    --  -48.45-125.00  60.00   44
 10  \w   -124.00 -84.00   1.00    0.40    --  -86.25 -99.00  60.00   40
 11  \w   -154.00-127.00   1.00    0.40    --  -86.25 -99.00  60.00   27
 12  \w     88.00 172.00   1.00    0.40    --  107.75  77.00-150.00   84
 13  \w    105.00 137.00   1.00    0.40    --  107.75  19.00  30.00   32
 14  \w     36.00 117.00   1.00    0.40    --  107.75-125.00-150.00   81
 15  \w     35.00 104.00   1.00    0.40    --  107.75 -99.00-150.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0349226000
_diffrn_orient_matrix_UB_12      -0.0821113000
_diffrn_orient_matrix_UB_13      0.0456394000
_diffrn_orient_matrix_UB_21      0.1518198000
_diffrn_orient_matrix_UB_22      -0.1182647000
_diffrn_orient_matrix_UB_23      -0.0207996000
_diffrn_orient_matrix_UB_31      0.1596902000
_diffrn_orient_matrix_UB_32      0.1302024000
_diffrn_orient_matrix_UB_33      0.0098231000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9254
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.003
_diffrn_reflns_theta_min         5.768
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    15.154
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00449
_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 light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.284
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.156
_refine_ls_abs_structure_details
;
 Flack x determined using 1068 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.001(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2915
_refine_ls_number_restraints     120
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0927P)^2^+5.0290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1451
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                2733
_reflns_number_total             2915
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05875c2.cif
_cod_data_source_block           180728b
_cod_depositor_comments
'Adding full bibliography for 1557107--1557109.cif.'
_cod_database_code               1557109
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CNI
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.518
_reflns_odcompleteness_completeness 99.89
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.004 and
sigma for terminal atoms of 0.008
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.004 and
sigma for terminal atoms of 0.008
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              88740
_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 104.529
_oxdiff_exptl_absorpt_empirical_full_min 0.481