Synthesis of 2-aminoBODIPYs by palladium catalysed amination
Alnoman, Rua Bandar; Stachelek, Patrycja; Knight, Julian G.; Harriman, Anthony; Waddell, Paul G.; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01767G

data_7155856
_publ_section_title
;
 Synthesis of 2-aminoBODIPYs by palladium catalysed amination
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01767G
_journal_year                    2017
_chemical_formula_moiety         'C29 H32 B F2 N3'
_chemical_formula_sum            'C29 H32 B F2 N3'
_chemical_formula_weight         471.38
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2017-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.325(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.3605(3)
_cell_length_b                   11.6571(3)
_cell_length_c                   21.6409(8)
_cell_measurement_reflns_used    13371
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      66.8000
_cell_measurement_theta_min      3.7810
_cell_volume                     5136.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -59.00  -32.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.5905  137.0000 -115.0000 27

  2 omega   54.00  117.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       41.5905   38.0000 -150.0000 63

  3 omega  -15.00   80.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       41.5905  -99.0000  150.0000 95

  4 omega   89.00  115.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       41.5905  132.0000   67.0000 26

  5 omega   32.00   68.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -120.0000 36

  6 omega  113.00  176.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  120.0000 63

  7 omega   16.00   41.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -150.0000 25

  8 omega   71.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000   30.0000 25

  9 omega   17.00   43.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  150.0000 26

 10 omega   31.00   57.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   60.0000 26

 11 omega   20.00   73.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  -30.0000 53

 12 omega   50.00   76.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  120.0000 26

 13 omega   26.00   58.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000   30.0000 32

 14 omega   29.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -30.0000 48

 15 omega   92.00  120.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -150.0000 28

 16 omega   36.00   70.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -150.0000 34

 17 omega   21.00   47.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  120.0000 26

 18 omega   22.00   71.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000   90.0000 49

 19 omega   82.00  146.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000   90.0000 64

 20 omega   84.00  123.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -120.0000 39

 21 omega   25.00   65.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   60.0000 40

 22 omega   26.00   60.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000    0.0000 34

 23 omega   23.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000 -180.0000 67

 24 omega   96.00  122.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000 -180.0000 26

 25 omega  130.00  156.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  150.0000 26

 26 omega   16.00   59.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  -90.0000 43

 27 omega    8.00   64.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       41.5905   77.0000   90.0000 56

 28 omega   12.00  116.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       41.5905   57.0000  -60.0000 104
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0246807000
_diffrn_orient_matrix_UB_12      -0.0565241000
_diffrn_orient_matrix_UB_13      0.0598623000
_diffrn_orient_matrix_UB_21      0.0375221000
_diffrn_orient_matrix_UB_22      0.0901218000
_diffrn_orient_matrix_UB_23      0.0384660000
_diffrn_orient_matrix_UB_31      -0.0609181000
_diffrn_orient_matrix_UB_32      0.0783800000
_diffrn_orient_matrix_UB_33      -0.0010699000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.962
_diffrn_reflns_theta_min         4.086
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     651
_refine_ls_number_reflns         9089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+1.3274P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1043
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7261
_reflns_number_total             9089
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01767g2.cif
_cod_data_source_block           jgk150008
_cod_original_cell_volume        5136.2(2)
_cod_database_code               7155856
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C29 H32 B1 F2 N3'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C51(H51A,H51B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C25(H25), C26(H26), C28(H28),
 C29(H29), C44(H44), C45(H45), C46(H46), C47(H47), C55(H55), C56(H56), C58(H58),
  C59(H59)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C), C41(H41A,
 H41B,H41C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C),
 C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C60(H60A,H60B,H60C)
;
_shelx_res_checksum              86124
_olex2_submission_special_instructions 'No special instructions were received'