Iridium-catalysed 3,5-bis-borylation of phthalonitrile enables access to a family of C<sub>4h</sub> octaarylphthalocyanines.
Mulholland, Katie D.; Yoon, Sangbin; Rennie, Christopher C.; Sitch, Eleanor K.; McKay, Alasdair I.; Edkins, Katharina; Edkins, Robert M.; Chemical communications (Cambridge, England) 56 (2020) 8452–8455; doi:10.1039/d0cc03161e

data_7126716
_publ_section_title
;
 Iridium-catalysed 3,5-bis-borylation of phthalonitrile enables access to
 a family of C<sub>4h</sub> octaarylphthalocyanines.
;
_journal_issue                   60
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8452
_journal_page_last               8455
_journal_paper_doi               10.1039/d0cc03161e
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C24 H20 N2 O4'
_chemical_formula_sum            'C24 H20 N2 O4'
_chemical_formula_weight         400.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2020-03-10 deposited with the CCDC.	2020-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                87.763(5)
_cell_angle_beta                 74.272(6)
_cell_angle_gamma                87.728(6)
_cell_formula_units_Z            2
_cell_length_a                   7.6587(6)
_cell_length_b                   11.0602(8)
_cell_length_c                   12.3929(8)
_cell_measurement_reflns_used    2658
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.5090
_cell_measurement_theta_min      2.5660
_cell_volume                     1009.23(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0756
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -36.00  51.00   1.00    7.50    --  -17.48  57.00  60.00   87
  2  \w    -24.00  24.00   1.00    7.50    --  -17.48-100.00 -60.00   48
  3  \w    -24.00  24.00   1.00    7.50    --  -17.48-100.00  90.00   48
  4  \w    -40.00  53.00   1.00    7.50    --  -17.48  38.00 -60.00   93
  5  \w     -1.00  86.00   1.00    7.50    --   17.95  57.00 -30.00   87
  6  \w    -51.00  47.00   1.00    7.50    --   17.95 -77.00-180.00   98
  7  \w     35.00  92.00   1.00    7.50    --   17.95 178.00  90.00   57
  8  \w     -1.00  15.00   1.00    7.50    --   17.95  57.00-150.00   16
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0299349000
_diffrn_orient_matrix_UB_12      -0.0575569000
_diffrn_orient_matrix_UB_13      -0.0093765000
_diffrn_orient_matrix_UB_21      -0.0782900000
_diffrn_orient_matrix_UB_22      0.0278724000
_diffrn_orient_matrix_UB_23      -0.0115003000
_diffrn_orient_matrix_UB_31      0.0473347000
_diffrn_orient_matrix_UB_32      0.0057538000
_diffrn_orient_matrix_UB_33      -0.0576059000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11573
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.48
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3176
_exptl_crystal_description       block
_exptl_crystal_F_000             420.2185
_exptl_crystal_preparation       'Cut from a larger crystal'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.294
_exptl_crystal_size_min          0.154
_refine_diff_density_max         0.4157
_refine_diff_density_min         -0.4030
_refine_diff_density_rms         0.0945
_refine_ls_d_res_high            0.8106
_refine_ls_d_res_low             8.2250
_refine_ls_goodness_of_fit_ref   1.0487
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0487
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.0143P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1194
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -8
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2619
_reflns_number_total             3968
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0cc03161e2.cif
_cod_data_source_block           KE072
_cod_depositor_comments
'Adding full bibliography for 7126716--7126723.cif.'
_cod_database_code               7126716
_chemical_oxdiff_formula         'C24 H20 O2 N2'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C8(H8), C11(H11), C12(H12), C14(H14), C15(H15), C20(H20), C25(H25), C30(H30)
2.b Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C21(H21a,H21b,H21c), C22(H22a,H22b,H22c), C28(H28a,H28b,
 H28c)
;
_olex2_date_sample_data_collection 2017-04-18
_olex2_exptl_crystal_mounting_method
'Crystal soaked in perfluoro polyether oil and mounted on MiTeGen sample holder directly into the precooled cryostream.'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.092
_oxdiff_exptl_absorpt_empirical_full_min 0.898