#------------------------------------------------------------------------------
#$Date: 2019-11-24 10:07:13 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237580 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/73/7237304.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7237304
loop_
_publ_author_name
'Melville, Owen A.'
'Grant, Trevor M.'
'Lessard, Benoît H.'
_publ_section_title
;
 Silicon phthalocyanines as N-type semiconductors in organic thin film
 transistors
;
_journal_issue                   20
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              5482
_journal_paper_doi               10.1039/C8TC01116H
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C46 H26 N8 O4 Si'
_chemical_formula_sum            'C46 H26 N8 O4 Si'
_chemical_formula_weight         782.84
_chemical_name_systematic        'Bis(benzoate) silicon phthalocyanine'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-01-16 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                108.442(2)
_cell_angle_beta                 112.993(2)
_cell_angle_gamma                97.706(2)
_cell_formula_units_Z            1
_cell_length_a                   9.2516(5)
_cell_length_b                   10.4441(5)
_cell_length_c                   10.6544(5)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      67.14
_cell_measurement_theta_min      4.67
_cell_volume                     859.00(8)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19258
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.825
_diffrn_reflns_theta_min         4.671
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    1.132
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       Block
_exptl_crystal_F_000             404
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0326
_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/[σ²(Fo²)+(0.0346P)²+0.5112P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0821
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2944
_reflns_number_total             3049
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8tc01116h2.cif
_cod_data_source_block           d15153_A
_cod_database_code               7237304
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.805
_shelx_estimated_absorpt_t_max   0.849
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Si1 Si 0.5000 0.5000 0.5000 0.01535(13) Uani 1 2 d S . P
O1 O 0.56876(11) 0.36203(10) 0.54157(10) 0.0184(2) Uani 1 1 d . . .
O2 O 0.45350(13) 0.16878(11) 0.32630(11) 0.0299(3) Uani 1 1 d . . .
N1 N 0.72270(13) 0.61608(11) 0.62217(12) 0.0171(2) Uani 1 1 d . . .
N2 N 0.73691(14) 0.70010(12) 0.86818(12) 0.0190(3) Uani 1 1 d . . .
N3 N 0.46613(13) 0.54855(11) 0.67212(12) 0.0169(2) Uani 1 1 d . . .
N4 N 0.17803(14) 0.41810(12) 0.56213(13) 0.0197(3) Uani 1 1 d . . .
C1 C 0.79948(16) 0.69391(14) 0.77492(15) 0.0180(3) Uani 1 1 d . . .
C2 C 0.58108(16) 0.63362(14) 0.81833(15) 0.0177(3) Uani 1 1 d . . .
C3 C 0.50556(17) 0.64323(14) 0.91574(15) 0.0187(3) Uani 1 1 d . . .
C4 C 0.56653(18) 0.71133(15) 1.07005(16) 0.0227(3) Uani 1 1 d . . .
H4A H 0.6781 0.7666 1.1330 0.027 Uiso 1 1 calc R U .
C5 C 0.45771(19) 0.69491(15) 1.12707(16) 0.0255(3) Uani 1 1 d . . .
H5A H 0.4962 0.7377 1.2318 0.031 Uiso 1 1 calc R U .
C6 C 0.29156(19) 0.61650(16) 1.03418(17) 0.0266(3) Uani 1 1 d . . .
H6A H 0.2197 0.6090 1.0771 0.032 Uiso 1 1 calc R U .
C7 C 0.23085(18) 0.55024(15) 0.88181(16) 0.0233(3) Uani 1 1 d . . .
H7A H 0.1184 0.4977 0.8185 0.028 Uiso 1 1 calc R U .
C8 C 0.34142(17) 0.56365(14) 0.82483(15) 0.0190(3) Uani 1 1 d . . .
C9 C 0.32001(16) 0.50438(14) 0.67470(15) 0.0179(3) Uani 1 1 d . . .
C10 C 0.16093(16) 0.36243(14) 0.42572(15) 0.0181(3) Uani 1 1 d . . .
C11 C 0.00798(16) 0.26486(14) 0.30169(15) 0.0193(3) Uani 1 1 d . . .
C12 C -0.14105(17) 0.20803(15) 0.29536(17) 0.0230(3) Uani 1 1 d . . .
H12A H -0.1577 0.2348 0.3814 0.028 Uiso 1 1 calc R U .
C13 C -0.26391(17) 0.11054(16) 0.15766(17) 0.0260(3) Uani 1 1 d . . .
H13A H -0.3672 0.0695 0.1490 0.031 Uiso 1 1 calc R U .
C14 C -0.23887(18) 0.07124(15) 0.03095(17) 0.0256(3) Uani 1 1 d . . .
H14A H -0.3250 0.0031 -0.0614 0.031 Uiso 1 1 calc R U .
C15 C -0.09106(17) 0.12969(15) 0.03751(16) 0.0226(3) Uani 1 1 d . . .
H15A H -0.0746 0.1039 -0.0487 0.027 Uiso 1 1 calc R U .
C16 C 0.03270(16) 0.22812(14) 0.17606(15) 0.0191(3) Uani 1 1 d . . .
C17 C 0.55581(17) 0.23362(14) 0.45559(15) 0.0200(3) Uani 1 1 d . . .
C18 C 0.68389(17) 0.17406(15) 0.53336(15) 0.0200(3) Uani 1 1 d . . .
C19 C 0.6696(2) 0.03278(16) 0.46307(18) 0.0288(3) Uani 1 1 d . . .
H19A H 0.5768 -0.0251 0.3700 0.035 Uiso 1 1 calc R U .
C20 C 0.7907(2) -0.02375(17) 0.5285(2) 0.0348(4) Uani 1 1 d . . .
H20A H 0.7812 -0.1203 0.4801 0.042 Uiso 1 1 calc R U .
C21 C 0.9258(2) 0.06074(18) 0.6647(2) 0.0339(4) Uani 1 1 d . . .
H21A H 1.0083 0.0216 0.7099 0.041 Uiso 1 1 calc R U .
C22 C 0.94082(19) 0.20121(17) 0.73475(18) 0.0305(4) Uani 1 1 d . . .
H22A H 1.0337 0.2588 0.8279 0.037 Uiso 1 1 calc R U .
C23 C 0.82002(18) 0.25844(15) 0.66893(16) 0.0228(3) Uani 1 1 d . . .
H23A H 0.8306 0.3554 0.7168 0.027 Uiso 1 1 calc R U .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Si1 O1 180.0 . 2_666
O1 Si1 N3 92.42(4) . 2_666
O1 Si1 N3 87.58(4) 2_666 2_666
O1 Si1 N3 87.58(4) . .
O1 Si1 N3 92.42(4) 2_666 .
N3 Si1 N3 180.0 2_666 .
O1 Si1 N1 86.96(4) . .
O1 Si1 N1 93.04(4) 2_666 .
N3 Si1 N1 90.60(5) 2_666 .
N3 Si1 N1 89.40(5) . .
O1 Si1 N1 93.04(4) . 2_666
O1 Si1 N1 86.96(4) 2_666 2_666
N3 Si1 N1 89.40(5) 2_666 2_666
N3 Si1 N1 90.60(5) . 2_666
N1 Si1 N1 180.0 . 2_666
C17 O1 Si1 132.07(9) . .
C10 N1 C1 106.68(11) 2_666 .
C10 N1 Si1 126.16(9) 2_666 .
C1 N1 Si1 127.16(9) . .
C2 N2 C1 120.65(12) . .
C9 N3 C2 106.58(11) . .
C9 N3 Si1 126.04(9) . .
C2 N3 Si1 127.38(9) . .
C10 N4 C9 121.09(12) . .
N2 C1 N1 127.69(12) . .
N2 C1 C16 122.46(12) . 2_666
N1 C1 C16 109.85(12) . 2_666
N2 C2 N3 127.61(12) . .
N2 C2 C3 122.44(12) . .
N3 C2 C3 109.94(12) . .
C8 C3 C4 120.70(13) . .
C8 C3 C2 106.42(12) . .
C4 C3 C2 132.87(13) . .
C5 C4 C3 117.19(14) . .
C5 C4 H4A 121.4 . .
C3 C4 H4A 121.4 . .
C4 C5 C6 121.70(14) . .
C4 C5 H5A 119.2 . .
C6 C5 H5A 119.2 . .
C7 C6 C5 121.18(14) . .
C7 C6 H6A 119.4 . .
C5 C6 H6A 119.4 . .
C6 C7 C8 117.10(14) . .
C6 C7 H7A 121.4 . .
C8 C7 H7A 121.4 . .
C7 C8 C3 122.09(13) . .
C7 C8 C9 131.01(13) . .
C3 C8 C9 106.89(12) . .
N4 C9 N3 128.14(13) . .
N4 C9 C8 121.69(12) . .
N3 C9 C8 110.14(11) . .
N4 C10 N1 127.93(12) . 2_666
N4 C10 C11 121.98(13) . .
N1 C10 C11 110.08(12) 2_666 .
C16 C11 C12 121.97(13) . .
C16 C11 C10 106.83(12) . .
C12 C11 C10 131.17(13) . .
C13 C12 C11 116.91(14) . .
C13 C12 H12A 121.5 . .
C11 C12 H12A 121.5 . .
C12 C13 C14 121.40(14) . .
C12 C13 H13A 119.3 . .
C14 C13 H13A 119.3 . .
C15 C14 C13 121.42(13) . .
C15 C14 H14A 119.3 . .
C13 C14 H14A 119.3 . .
C14 C15 C16 117.25(14) . .
C14 C15 H15A 121.4 . .
C16 C15 H15A 121.4 . .
C11 C16 C15 121.03(13) . .
C11 C16 C1 106.49(12) . 2_666
C15 C16 C1 132.45(13) . 2_666
O2 C17 O1 124.97(13) . .
O2 C17 C18 122.07(13) . .
O1 C17 C18 112.96(12) . .
C23 C18 C19 119.81(13) . .
C23 C18 C17 121.48(13) . .
C19 C18 C17 118.60(13) . .
C20 C19 C18 120.02(15) . .
C20 C19 H19A 120.0 . .
C18 C19 H19A 120.0 . .
C19 C20 C21 119.93(15) . .
C19 C20 H20A 120.0 . .
C21 C20 H20A 120.0 . .
C22 C21 C20 120.29(14) . .
C22 C21 H21A 119.9 . .
C20 C21 H21A 119.9 . .
C21 C22 C23 119.90(15) . .
C21 C22 H22A 120.0 . .
C23 C22 H22A 120.0 . .
C18 C23 C22 120.03(14) . .
C18 C23 H23A 120.0 . .
C22 C23 H23A 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 O1 1.7626(9) .
Si1 O1 1.7627(9) 2_666
Si1 N3 1.9030(11) 2_666
Si1 N3 1.9030(11) .
Si1 N1 1.9093(11) .
Si1 N1 1.9093(11) 2_666
O1 C17 1.3213(17) .
O2 C17 1.2130(17) .
N1 C10 1.3808(18) 2_666
N1 C1 1.3852(17) .
N2 C2 1.3201(18) .
N2 C1 1.3211(18) .
N3 C9 1.3823(17) .
N3 C2 1.3870(17) .
N4 C10 1.3178(18) .
N4 C9 1.3206(18) .
C1 C16 1.4508(19) 2_666
C2 C3 1.4474(19) .
C3 C8 1.392(2) .
C3 C4 1.398(2) .
C4 C5 1.382(2) .
C4 H4A 0.9500 .
C5 C6 1.405(2) .
C5 H5A 0.9500 .
C6 C7 1.379(2) .
C6 H6A 0.9500 .
C7 C8 1.391(2) .
C7 H7A 0.9500 .
C8 C9 1.4401(19) .
C10 N1 1.3808(18) 2_666
C10 C11 1.4448(19) .
C11 C16 1.389(2) .
C11 C12 1.393(2) .
C12 C13 1.387(2) .
C12 H12A 0.9500 .
C13 C14 1.401(2) .
C13 H13A 0.9500 .
C14 C15 1.386(2) .
C14 H14A 0.9500 .
C15 C16 1.3967(19) .
C15 H15A 0.9500 .
C16 C1 1.4509(19) 2_666
C17 C18 1.4947(19) .
C18 C23 1.387(2) .
C18 C19 1.388(2) .
C19 C20 1.384(2) .
C19 H19A 0.9500 .
C20 C21 1.387(2) .
C20 H20A 0.9500 .
C21 C22 1.378(2) .
C21 H21A 0.9500 .
C22 C23 1.389(2) .
C22 H22A 0.9500 .
C23 H23A 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N3 Si1 O1 C17 -34.16(12) 2_666 .
N3 Si1 O1 C17 145.84(12) . .
N1 Si1 O1 C17 -124.64(12) . .
N1 Si1 O1 C17 55.36(12) 2_666 .
C2 N2 C1 N1 -4.2(2) . .
C2 N2 C1 C16 176.35(12) . 2_666
C10 N1 C1 N2 -176.93(13) 2_666 .
Si1 N1 C1 N2 2.6(2) . .
C10 N1 C1 C16 2.61(14) 2_666 2_666
Si1 N1 C1 C16 -177.81(9) . 2_666
C1 N2 C2 N3 2.2(2) . .
C1 N2 C2 C3 -176.90(12) . .
C9 N3 C2 N2 -179.16(13) . .
Si1 N3 C2 N2 1.1(2) . .
C9 N3 C2 C3 0.08(14) . .
Si1 N3 C2 C3 -179.71(8) . .
N2 C2 C3 C8 178.41(12) . .
N3 C2 C3 C8 -0.87(15) . .
N2 C2 C3 C4 -2.4(2) . .
N3 C2 C3 C4 178.30(14) . .
C8 C3 C4 C5 0.5(2) . .
C2 C3 C4 C5 -178.52(14) . .
C3 C4 C5 C6 -1.7(2) . .
C4 C5 C6 C7 1.2(2) . .
C5 C6 C7 C8 0.5(2) . .
C6 C7 C8 C3 -1.7(2) . .
C6 C7 C8 C9 177.31(14) . .
C4 C3 C8 C7 1.2(2) . .
C2 C3 C8 C7 -179.53(12) . .
C4 C3 C8 C9 -178.02(12) . .
C2 C3 C8 C9 1.26(14) . .
C10 N4 C9 N3 -0.5(2) . .
C10 N4 C9 C8 -178.68(12) . .
C2 N3 C9 N4 -177.60(13) . .
Si1 N3 C9 N4 2.2(2) . .
C2 N3 C9 C8 0.73(14) . .
Si1 N3 C9 C8 -179.48(8) . .
C7 C8 C9 N4 -1.9(2) . .
C3 C8 C9 N4 177.17(12) . .
C7 C8 C9 N3 179.61(13) . .
C3 C8 C9 N3 -1.28(15) . .
C9 N4 C10 N1 -1.3(2) . 2_666
C9 N4 C10 C11 178.31(12) . .
N4 C10 C11 C16 179.70(12) . .
N1 C10 C11 C16 -0.64(15) 2_666 .
N4 C10 C11 C12 -2.0(2) . .
N1 C10 C11 C12 177.70(13) 2_666 .
C16 C11 C12 C13 1.1(2) . .
C10 C11 C12 C13 -177.05(14) . .
C11 C12 C13 C14 0.0(2) . .
C12 C13 C14 C15 -0.9(2) . .
C13 C14 C15 C16 0.8(2) . .
C12 C11 C16 C15 -1.3(2) . .
C10 C11 C16 C15 177.27(12) . .
C12 C11 C16 C1 -179.47(12) . 2_666
C10 C11 C16 C1 -0.94(14) . 2_666
C14 C15 C16 C11 0.3(2) . .
C14 C15 C16 C1 177.97(14) . 2_666
Si1 O1 C17 O2 -21.6(2) . .
Si1 O1 C17 C18 157.56(9) . .
O2 C17 C18 C23 166.10(14) . .
O1 C17 C18 C23 -13.07(19) . .
O2 C17 C18 C19 -10.2(2) . .
O1 C17 C18 C19 170.66(13) . .
C23 C18 C19 C20 0.3(2) . .
C17 C18 C19 C20 176.59(14) . .
C18 C19 C20 C21 0.3(3) . .
C19 C20 C21 C22 -0.5(3) . .
C20 C21 C22 C23 0.2(3) . .
C19 C18 C23 C22 -0.6(2) . .
C17 C18 C23 C22 -176.86(14) . .
C21 C22 C23 C18 0.4(2) . .
