Aluminum Chloride Mediated Alkynylation of Boron Subphthalocyanine Chloride Using Trimethylsilyl-Capped Acetylenes.
Gotfredsen, Henrik; Jevric, Martyn; Broman, Søren L; Petersen, Anne U.; Nielsen, Mogens Brøndsted; The Journal of organic chemistry 81 (2016) 1–5; doi:10.1021/acs.joc.5b02719

data_4036551
_publ_section_title
;
 Aluminum Chloride Mediated Alkynylation of Boron Subphthalocyanine
 Chloride Using Trimethylsilyl-Capped Acetylenes.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1
_journal_page_last               5
_journal_paper_doi               10.1021/acs.joc.5b02719
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C33 H19 B N6 O'
_chemical_formula_sum            'C33 H19 B N6 O'
_chemical_formula_weight         526.35
_chemical_melting_point          'above 230'
_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_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-11-26
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                82.680(3)
_cell_angle_beta                 70.815(3)
_cell_angle_gamma                83.638(3)
_cell_formula_units_Z            2
_cell_length_a                   9.8803(7)
_cell_length_b                   10.8574(7)
_cell_length_c                   12.6802(9)
_cell_measurement_reflns_used    7889
_cell_measurement_temperature    122(2)
_cell_measurement_theta_max      31.70
_cell_measurement_theta_min      2.67
_cell_volume                     1270.79(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      122
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23899
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         2.188
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7411
_exptl_absorpt_correction_T_min  0.7229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1516 before and 0.0676 after correction.
The Ratio of minimum to maximum transmission is 0.9754.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       Rod
_exptl_crystal_F_000             548
_exptl_crystal_recrystallization_method
'crystals grown from chloroform/heptane'
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         5593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0457P)^2^+0.3925P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1060
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4318
_reflns_number_total             5593
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02719_si_002.cif
_cod_data_source_block           mo_d8v1394_0m-1
_cod_database_code               4036551
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
;
_shelx_res_checksum              72449
_shelx_hkl_checksum              11047
_olex2_submission_special_instructions 'No special instructions were received'