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_4036552
_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         'C41 H29 B Fe N6 Si'
_chemical_formula_sum            'C41 H29 B Fe N6 Si'
_chemical_formula_weight         700.49
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-11-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                91.609(4)
_cell_angle_beta                 94.080(5)
_cell_angle_gamma                104.775(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0159(11)
_cell_length_b                   12.6153(13)
_cell_length_c                   17.649(2)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    122(2)
_cell_measurement_theta_max      29.56
_cell_measurement_theta_min      2.32
_cell_volume                     1719.4(4)
_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    'XS (Sheldrick, 2008)'
_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  0.1113
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            67746
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.696
_diffrn_reflns_theta_min         2.316
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.514
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1642 before and 0.0861 after correction.
The Ratio of minimum to maximum transmission is 0.8549.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       Plate
_exptl_crystal_F_000             724
_exptl_crystal_recrystallization_method
'crystals grown from Ethylacetate /heptane'
_exptl_crystal_size_max          0.611
_exptl_crystal_size_mid          0.318
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         8864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0453P)^2^+1.6061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1192
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6734
_reflns_number_total             8864
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02719_si_004.cif
_cod_data_source_block           mo_d8v1426_0m-1
_cod_original_cell_volume        1719.3(4)
_cod_database_code               4036552
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.744
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              99623
_shelx_hkl_checksum              35856
_olex2_submission_special_instructions 'No special instructions were received'