Crystal structures of bis(phenoxy)silicon phthalocyanines: increasing π‒π interactions, solubility and disorder and no halogen bonding observed
Lessard, Beno\?ît H.; Lough, Alan J.; Bender, Timothy P.; Acta Crystallographica Section E 72 (2016) 988–994; doi:10.1107/S205698901600935X

data_2241737
_publ_section_title
;
 Crystal structures of bis(phenoxy)silicon phthalocyanines: increasing
 \p--\p interactions, solubility and disorder and no halogen bonding
 observed
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              988
_journal_page_last               994
_journal_paper_doi               10.1107/S205698901600935X
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C52 H42 N8 O2 Si'
_chemical_formula_moiety         'C52 H42 N8 O2 Si'
_chemical_formula_sum            'C52 H42 N8 O2 Si'
_chemical_formula_weight         839.03
_chemical_name_systematic
;
Bis(3-iodophenoxy)(phthalocyanine)silicon
;
_space_group_IT_number           73
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-I 2b 2c'
_symmetry_space_group_name_H-M   'I b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.9239(3)
_cell_length_b                   25.7282(7)
_cell_length_c                   33.2065(8)
_cell_measurement_reflns_used    586
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      35.12
_cell_measurement_theta_min      4.35
_cell_volume                     9332.8(4)
_computing_cell_refinement
;
SAINT (Bruker, 2011)
;
_computing_data_collection
;
APEX2 (Bruker, 2011)
;
_computing_data_reduction
;
SAINT (Bruker, 2011)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2006)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Kappa APEX DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            120855
_diffrn_reflns_theta_full        66.79
_diffrn_reflns_theta_max         66.79
_diffrn_reflns_theta_min         3.44
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>TWINABS</i>; Bruker, 2007)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3520
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_platon_squeeze_details
;
During the
refinement of the structure, electron density peaks were located
that were believed to be highly disordered
solvent molecules (possibly pentane/dichloromethane). Attempts
made to model the solvent molecule were not successful.
The SQUEEZE option in PLATON (Spek, 2009) indicated there was a
large solvent cavity 367 A3. In the final cycles of refinement,
this contribution (99 electrons) 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, 2009). 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. (2009). <i>Acta Cryst.</i> <b>D65</b>, 148--155.
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         0.401
_refine_diff_density_min         -0.364
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4085
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0662
_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^)+(0.1166P)^2^+6.9892P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1968
_refine_ls_wR_factor_ref         0.2084
_reflns_number_gt                2969
_reflns_number_total             4085
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            hb7581sup1.cif
_cod_data_source_block           2secBP2-SiPc
_cod_database_code               2241737
_cod_database_fobs_code 2241737