Bioorthogonally Applicable Multicolor Fluorogenic Naphthalimide-Tetrazine Probes with Aggregation-Induced Emission Characters
Wang, Yongcheng; Teng, Yu; Yang, Hong; Li, Xiang; Yin, Dali; Tian, Yulin; Chemical Communications  (2021) –; doi:10.1039/D1CC05204G

data_7129353
_publ_section_title
;
 Bioorthogonally Applicable Multicolor Fluorogenic Naphthalimide-Tetrazine
 Probes with Aggregation-Induced Emission Characters
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05204G
_journal_year                    2021
_chemical_formula_moiety         'C33 H33 N3 O3'
_chemical_formula_sum            'C33 H33 N3 O3'
_chemical_formula_weight         519.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-11-13 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 130.84(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.443(6)
_cell_length_b                   9.3730(5)
_cell_length_c                   23.143(4)
_cell_measurement_reflns_used    2150
_cell_measurement_temperature    292.98(10)
_cell_measurement_theta_max      71.5010
_cell_measurement_theta_min      3.5580
_cell_volume                     5324(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -21.00  32.00   1.00    4.00    --  -41.11  77.00 120.00   53
  2  \w    -69.00  32.00   1.00    4.00    --  -41.11  57.00 -90.00  101
  3  \w    -84.00 -42.00   1.00    4.00    --  -41.11 -38.00 -60.00   42
  4  \w     69.00  95.00   1.00    4.00    --   41.11-125.00 -90.00   26
  5  \w     61.00 120.00   1.00    6.00    --  106.95-125.00-150.00   59
  6  \w     33.00 120.00   1.00    6.00    --  106.95 -77.00  30.00   87
  7  \w     81.00 107.00   1.00    6.00    --  106.95-125.00  60.00   26
  8  \w     35.00  60.00   1.00    6.00    --  106.95-125.00  60.00   25
  9  \w     37.00  63.00   1.00    6.00    --  106.95 -45.00 150.00   26
 10  \w     89.00 178.00   1.00    6.00    --  106.95  30.00 -60.00   89
 11  \w     80.00 177.00   1.00    6.00    --  106.95  30.00-150.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0562151000
_diffrn_orient_matrix_UB_12      0.0488067000
_diffrn_orient_matrix_UB_13      0.0736292000
_diffrn_orient_matrix_UB_21      0.0217917000
_diffrn_orient_matrix_UB_22      -0.0005862000
_diffrn_orient_matrix_UB_23      -0.0424363000
_diffrn_orient_matrix_UB_31      -0.0173830000
_diffrn_orient_matrix_UB_32      0.1569536000
_diffrn_orient_matrix_UB_33      -0.0229538000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9064
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         3.602
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0760
_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^)+(0.1296P)^2^+2.0706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2175
_refine_ls_wR_factor_ref         0.2520
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2927
_reflns_number_total             4687
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05204g2.cif
_cod_data_source_block           3-5b_2
_cod_original_cell_volume        5324(2)
_cod_database_code               7129353
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.63
_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 C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(H26A)=Sof(H28C)=Sof(H28D)=Sof(C34)=Sof(H34A)=Sof(H34B)=1-FVAR(1)
 Sof(H26)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H28A)=Sof(H28B)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C26(H26), C26(H26A)
3.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B), C28(H28C,
 H28D), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B),
 C34(H34A,H34B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C17(H17),
 C18(H18)
3.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C33(H33A,H33B,H33C)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              26103
_shelx_hkl_checksum              23798
_olex2_date_sample_data_collection 2021-11-05
_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 1.655
_oxdiff_exptl_absorpt_empirical_full_min 0.404