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_7121277
_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         'C20 H20 B F2 N3 O'
_chemical_formula_sum            'C20 H20 B F2 N3 O'
_chemical_formula_weight         367.20
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc1yw140
_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                 115.235(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2429(5)
_cell_length_b                   8.7432(2)
_cell_length_c                   15.0494(4)
_cell_measurement_reflns_used    4029
_cell_measurement_temperature    294.24(10)
_cell_measurement_theta_max      72.2610
_cell_measurement_theta_min      5.8920
_cell_volume                     1814.25(10)
_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      294.24(10)
_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 0.984
_diffrn_measurement_details
;
  1 omega    2.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   90.0000   27.3584 30

  2 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -19.0000   60.0000 101

  3 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000 -120.0000 88

  4 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   30.0000 84

  5 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   30.0000 84

  6 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  150.0000 74

  7 omega   40.00   98.00   1.0000    2.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

  8 omega   81.00  176.00   1.0000    2.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 95

  9 omega   40.00  135.00   1.0000    2.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 95

 10 omega   38.00   91.00   1.0000    2.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 11 omega   38.00  116.00   1.0000    2.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 78

 12 omega   39.00  109.00   1.0000    2.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 13 omega   40.00   98.00   1.0000    2.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 14 omega   71.00  164.00   1.0000    2.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  160.0000 -138.0000 93

 15 omega   38.00   91.00   1.0000    2.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 16 omega   87.00  178.00   1.0000    2.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 91

 17 omega   17.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  150.0000 56
;
_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      -0.0995666000
_diffrn_orient_matrix_UB_12      -0.0791296000
_diffrn_orient_matrix_UB_13      -0.0493879000
_diffrn_orient_matrix_UB_21      -0.0483831000
_diffrn_orient_matrix_UB_22      0.1556628000
_diffrn_orient_matrix_UB_23      -0.0392270000
_diffrn_orient_matrix_UB_31      0.0151979000
_diffrn_orient_matrix_UB_32      -0.0233617000
_diffrn_orient_matrix_UB_33      -0.0939532000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10494
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.593
_diffrn_reflns_theta_min         5.897
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60577
_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    1.344
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0795
_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^)+(0.1396P)^2^+0.1569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1858
_refine_ls_wR_factor_ref         0.1974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3020
_reflns_number_total             3551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc00238j2.cif
_cod_data_source_block           yjs-zhx-1468
_cod_depositor_comments
'Adding full bibliography for 7121276--7121277.cif.'
_cod_database_code               7121277
_shelx_shelxl_version_number     2014/7
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00C), C00K(H00G,H00K), C00M(H00L,H00M), C00P(H00P,H00Q)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I),
 C00J(H00J), C00N(H00N), C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00R(H00R,H00S,H00T)
;
_olex2_date_sample_data_collection 2017-10-23
_olex2_submission_special_instructions 'No special instructions were received'