Silver-mediated direct C-H amination of BODIPYs for screening endoplasmic reticulum-targeting reagents.
Zhang, Huaxing; Chen, Xingyu; Lan, Jingbo; Liu, Yanhong; Zhou, Fulin; Wu, Di; You, Jingsong; Chemical communications (Cambridge, England) 54 (2018) 3219–3222; doi:10.1039/c8cc00238j

data_7121276
_publ_section_title
;
 Silver-mediated direct C-H amination of BODIPYs for screening endoplasmic
 reticulum-targeting reagents.
;
_journal_issue                   26
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3219
_journal_page_last               3222
_journal_paper_doi               10.1039/c8cc00238j
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C30 H21 B F2 N6'
_chemical_formula_sum            'C30 H21 B F2 N6'
_chemical_formula_weight         514.34
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc1yw13z
_audit_creation_date             2017-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-12-26 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.691(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0347(3)
_cell_length_b                   13.6496(4)
_cell_length_c                   17.0188(6)
_cell_measurement_reflns_used    6274
_cell_measurement_temperature    278(6)
_cell_measurement_theta_max      72.5680
_cell_measurement_theta_min      4.2360
_cell_volume                     2455.36(14)
_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)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      278(6)
_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 0.985
_diffrn_measurement_details
;
  1 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000    0.0000 84

  2 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000   60.0000 84

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

  4 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000 -180.0000 84

  5 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000   60.0000 66

  6 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000 -180.0000 84

  7 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  120.0000 66

  8 omega   39.00  109.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

  9 omega   87.00  178.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 91

 10 omega   41.00  126.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   60.0000 85

 11 omega   40.00   98.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 12 omega   38.00   91.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 13 omega   91.00  176.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 85

 14 omega   91.00  176.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 85

 15 omega   38.00   91.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 16 omega   38.00  116.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

 17 omega   19.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  -90.0000 80
;
_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      0.1405898000
_diffrn_orient_matrix_UB_12      -0.0244368000
_diffrn_orient_matrix_UB_13      0.0119477000
_diffrn_orient_matrix_UB_21      0.0348783000
_diffrn_orient_matrix_UB_22      0.0496934000
_diffrn_orient_matrix_UB_23      0.0849237000
_diffrn_orient_matrix_UB_31      -0.0172805000
_diffrn_orient_matrix_UB_32      -0.0981115000
_diffrn_orient_matrix_UB_33      0.0398624000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13806
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.510
_diffrn_reflns_theta_min         4.224
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56232
_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    1.391
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0749
_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^)+(0.1195P)^2^+0.3887P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.1832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4123
_reflns_number_total             4793
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc00238j2.cif
_cod_data_source_block           yjs-zhx-1540
_cod_depositor_comments
'Adding full bibliography for 7121276--7121277.cif.'
_cod_original_cell_volume        2455.35(13)
_cod_database_code               7121276
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.85
_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.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V),
 C00W(H00W), C00X(H00X), C00Z(H00Z), C010(H010), C011(H011), C013(H013)
2.b Idealised Me refined as rotating group:
 C00Y(H00A,H00C,H00D)
;
_olex2_submission_special_instructions 'No special instructions were received'