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_7127486
_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         'C53 H34 N O, B F4'
_chemical_formula_sum            'C53 H34 B F4 N O'
_chemical_formula_weight         787.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-09-29 deposited with the CCDC.	2020-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.350(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.3530(5)
_cell_length_b                   13.2053(3)
_cell_length_c                   20.2472(7)
_cell_measurement_reflns_used    6611
_cell_measurement_temperature    296.4(7)
_cell_measurement_theta_max      72.1550
_cell_measurement_theta_min      4.6360
_cell_volume                     4301.2(2)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.4(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
  1 omega   10.00  104.00   1.0000    5.4400
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000  -90.0000 94

  2 omega   20.00  104.00   1.0000    5.4400
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000   30.0000 84

  3 omega  -31.00   63.00   1.0000    5.4400
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -77.0000  120.0000 94

  4 omega  -31.00   53.00   1.0000    5.4400
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000 -120.0000 84

  5 omega   20.00  104.00   1.0000    5.4400
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000 -120.0000 84

  6 omega   18.00  106.00   1.0000    5.4400
omega____ theta____ kappa____ phi______ frames
    -       36.4171   38.0000 -180.0000 88

  7 omega    1.00   75.00   1.0000    5.4400
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000    0.0000 74

  8 omega   40.00   98.00   1.0000   21.7500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

  9 omega   38.00   91.00   1.0000   21.7500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 10 omega   57.00  150.00   1.0000   21.7500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   60.0000 93

 11 omega   38.00   91.00   1.0000   21.7500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 12 omega   38.00   91.00   1.0000   21.7500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 13 omega   39.00  109.00   1.0000   21.7500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 14 omega   94.00  175.00   1.0000   21.7500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 81

 15 omega   48.00  109.00   1.0000   21.7500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 61

 16 omega   39.00   72.00   1.0000   21.7500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 33

 17 omega   43.00  132.00   1.0000   21.7500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 89
;
_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      0.0077923000
_diffrn_orient_matrix_UB_12      -0.0095839000
_diffrn_orient_matrix_UB_13      -0.0744689000
_diffrn_orient_matrix_UB_21      -0.0947504000
_diffrn_orient_matrix_UB_22      -0.0144816000
_diffrn_orient_matrix_UB_23      -0.0191516000
_diffrn_orient_matrix_UB_31      -0.0111244000
_diffrn_orient_matrix_UB_32      0.1153843000
_diffrn_orient_matrix_UB_33      -0.0085628000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24708
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.641
_diffrn_reflns_theta_min         4.332
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70751
_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 orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       plate
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.803
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         8346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0768
_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^)+(0.1653P)^2^+0.4138P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2365
_refine_ls_wR_factor_ref         0.2564
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6263
_reflns_number_total             8346
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc06997c2.cif
_cod_data_source_block           yjs-cxy-1
_cod_database_code               7127486
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C00G(H00G), C00M(H00M), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013),
 C014(H014), C015(H015), C016(H016), C017(H017), C018(H018), C019(H019),
 C01A(H01A), C01B(H01B), C01C(H01C), C01D(H01D), C01F(H01F), C01G(H01G),
 C01H(H01H), C01I(H01I), C01K(H01K), C01L(H01L)
;
_shelx_res_checksum              34720
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2018-08-18
_olex2_submission_special_instructions 'No special instructions were received'