Switchable cascade C-H annulation to polycyclic pyryliums and pyridiniums: discovering mitochondria-targeting fluorescent probes.
Chen, Xingyu; Yan, Lipeng; Liu, Yanhong; Yang, Yudong; You, Jingsong; Chemical communications (Cambridge, England) 56 (2020) 15080–15083; doi:10.1039/d0cc06997c

data_7127487
_publ_section_title
;
 Switchable cascade C-H annulation to polycyclic pyryliums and
 pyridiniums: discovering mitochondria-targeting fluorescent probes.
;
_journal_issue                   95
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              15080
_journal_page_last               15083
_journal_paper_doi               10.1039/d0cc06997c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C0.5 H Cl, C53 H33 O2, B0.5 F2'
_chemical_formula_sum            'C53.5 H34 B0.5 Cl F2 O2'
_chemical_formula_weight         787.66
_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_Hall           '-P 4bc'
_space_group_name_H-M_alt        'P 42/n :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2020-09-03 deposited with the CCDC.	2020-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.1081(4)
_cell_length_b                   19.1081(4)
_cell_length_c                   24.3996(6)
_cell_measurement_reflns_used    14394
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.2300
_cell_measurement_theta_min      4.3600
_cell_volume                     8908.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
  1 omega    9.00  104.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000    0.0000 95

  2 omega  -32.00   63.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -77.0000 -120.0000 95

  3 omega   16.00   84.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -116.0000  100.0000 68

  4 omega  -33.00   55.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -38.0000  120.0000 88

  5 omega   17.00  105.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000   30.0000 88

  6 omega    9.00  104.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000  -90.0000 95

  7 omega    1.00   75.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000  150.0000 74

  8 omega   38.00   91.00   1.0000   13.1200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

  9 omega   38.00   91.00   1.0000   13.1200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 10 omega   40.00  135.00   1.0000   13.1200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 95

 11 omega   38.00   91.00   1.0000   13.1200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 12 omega   39.00  109.00   1.0000   13.1200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 13 omega   39.00  109.00   1.0000   13.1200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 14 omega   38.00   91.00   1.0000   13.1200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 15 omega   81.00  176.00   1.0000   13.1200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 95

 16 omega   97.00  159.00   1.0000   13.1200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 62

 17 omega   40.00   89.00   1.0000   13.1200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0181700000
_diffrn_orient_matrix_UB_12      0.0448897000
_diffrn_orient_matrix_UB_13      -0.0504991000
_diffrn_orient_matrix_UB_21      -0.0051289000
_diffrn_orient_matrix_UB_22      0.0652385000
_diffrn_orient_matrix_UB_23      0.0368468000
_diffrn_orient_matrix_UB_31      0.0784113000
_diffrn_orient_matrix_UB_32      0.0145835000
_diffrn_orient_matrix_UB_33      -0.0092646000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            48707
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.751
_diffrn_reflns_theta_min         4.884
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.140
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       plate
_exptl_crystal_F_000             3268
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         8643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0899
_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^)+(0.1489P)^2^+8.0012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2573
_refine_ls_wR_factor_ref         0.2869
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5757
_reflns_number_total             8643
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc06997c2.cif
_cod_data_source_block           yjs-cxy-561_sq
_cod_original_cell_volume        8908.8(4)
_cod_original_sg_symbol_H-M      'P 42/n'
_cod_original_formula_sum        'C53.50 H34 B0.50 Cl F2 O2'
_cod_database_code               7127487
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.56
_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
2. Others
 Fixed Sof: H01B(0.5) H01K(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C01S(H01B,H01K)
3.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00K(H00K), C00Q(H00Q), C00S(H00S), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z),
 C010(H010), C011(H011), C013(H013), C015(H015), C016(H016), C017(H017),
 C018(H018), C019(H019), C01A(H01A), C01C(H01C), C01D(H01D), C01E(H01E),
 C01F(H01F), C01G(H01G), C01H(H01H), C01I(H01I), C01J(H01J), C01L(H01L),
 C01M(H01M), C01N(H01N), C2(H2)
;
_shelx_res_checksum              46301
_shelx_fab_checksum              75022
_olex2_date_sample_data_collection 2017-07-05
_olex2_submission_special_instructions 'No special instructions were received'