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_7127485
_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         'C25 H16 O2'
_chemical_formula_sum            'C25 H16 O2'
_chemical_formula_weight         348.38
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-31
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-09-03 deposited with the CCDC.	2020-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.672(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.30435(19)
_cell_length_b                   23.1463(4)
_cell_length_c                   9.7550(2)
_cell_measurement_reflns_used    3856
_cell_measurement_temperature    296.75(18)
_cell_measurement_theta_max      72.1430
_cell_measurement_theta_min      5.1430
_cell_volume                     1776.37(7)
_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      296.75(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -30.0000 74

  2 omega  -18.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -83.0000  130.0000 84

  3 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   90.0000 84

  4 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -60.0000 84

  5 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   30.0000 74

  6 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -150.0000 84

  7 omega   38.00   91.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

  8 omega   39.00  109.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

  9 omega   38.00   91.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 10 omega   91.00  176.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 85

 11 omega   40.00   98.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 12 omega   40.00   98.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

 13 omega   40.00   98.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 14 omega   81.00  176.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 95

 15 omega   57.00  150.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  150.0000 93

 16 omega   20.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000    0.0000 43

 17 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -180.0000 94
;
_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      -0.0973977000
_diffrn_orient_matrix_UB_12      -0.0576884000
_diffrn_orient_matrix_UB_13      -0.0332548000
_diffrn_orient_matrix_UB_21      0.0743659000
_diffrn_orient_matrix_UB_22      -0.0115088000
_diffrn_orient_matrix_UB_23      -0.1232018000
_diffrn_orient_matrix_UB_31      0.1527599000
_diffrn_orient_matrix_UB_32      -0.0311566000
_diffrn_orient_matrix_UB_33      0.1072100000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9541
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.027
_diffrn_reflns_theta_max         67.027
_diffrn_reflns_theta_min         5.153
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57845
_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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0923P)^2^+0.1890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1484
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2738
_reflns_number_total             3168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc06997c2.cif
_cod_data_source_block           cxy-249
_cod_database_code               7127485
_reflns_odcompleteness_completeness 99.94
_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:
 C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R)
;
_shelx_res_checksum              62041
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-03-31
_olex2_submission_special_instructions 'No special instructions were received'