Pseudohalides of Boron Subphthalocyanine
Andrew S. Paton; Graham E. Morse; David Castelino; Timothy P. Bender; Journal of Organic Chemistry 77 (2012) 2531–2536; doi:10.1021/jo202365x

data_4027012
_publ_contact_author_address
;                       Department of Chemical Engineering and Applied Chemistry
                        University of Toronto
                        200 College St.
                        Ontario
                        Canada
                        M5S 3E5

            Department of Chemistry
            University of Toronto
            80 St. George St.
            Toronto
            Ontario, Canada
            M5S 3H6 
;
_publ_contact_author_email       TIM.BENDER@UTORONTO.CA
_publ_contact_author_name        'Timothy Bender'
_publ_section_title
;
 Pseudohalides of Boron Subphthalocyanine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2531
_journal_page_last               2536
_journal_paper_doi               10.1021/jo202365x
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C25 H15 B N6 O3 S'
_chemical_formula_sum            'C25 H15 B N6 O3 S'
_chemical_formula_weight         490.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.147(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.6367(11)
_cell_length_b                   10.6211(5)
_cell_length_c                   16.0322(4)
_cell_measurement_reflns_used    11425
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     4868.9(3)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f scans and \w scans with \k offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1135
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5489
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         2.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       needle
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
During the
refinement of the structure, electron density peaks were located
that were believed to be highly disordered
solvent molecules (possibly dichloromethane and/or pentane). Attempts
made to model the solvent molecule were not successful.
The SQUEEZE option in PLATON (Spek, 2003) indicated there was a
solvent cavity of volume 427 \%A^3^ containing approximately 96
electrons. In the final cycles of refinement, this contribution to the
electron density was removed from the observed data. The
density, the F(000) value, the molecular weight and the formula are
given without taking into account the results obtained with the
SQUEEZE option PLATON (Spek, 2003). Similar treatments of disordered
solvent molecules were carried out by St\"ahler et al. (2001),
Cox et al. (2003), Mohamed et al. (2003) and Athimoolam et al. (2005).
References:

Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13

Athimoolam, S., Kumar, J., Ramakrishnan, V. & Rajaram, R.K. (2005).
Acta Cryst. E61, m2014-m2017.

Cox, J.P., Kumarasammy, Y., Nahar, L., Sarkar D.S. & Shoeb, M.
(2003). Acta Cryst. E59, o975-o977.

Mohamed, A.A., Krause Bauer, A.J., Bruce, E.A. & Bruce M.R.M.
(2003). Acta Cryst. C59, m84-m86.

St\"ahler, R., N\"ather, C. & Bensch, W. (2001). Acta Cryst.
C57, 26-27.
;
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0966P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1847
_reflns_number_gt                2821
_reflns_number_total             5489
_reflns_threshold_expression     I.2\s(I)
_cod_data_source_file            jo202365x_si_002.cif
_cod_data_source_block           k11107
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4027012