#------------------------------------------------------------------------------
#$Date: 2019-11-23 16:03:12 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233933 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/61/7236116.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_7236116
loop_
_publ_author_name
'Lessard, Benoît H.'
'Grant, Trevor M.'
'White, Robin'
'Thibau, Emmanuel'
'Lu, Zheng-Hong'
'Bender, Timothy P.'
_publ_section_title
;
 The position and frequency of fluorine atoms changes the electron
 donor/acceptor properties of fluorophenoxy silicon phthalocyanines within
 organic photovoltaic devices
;
_journal_issue                   48
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              24512
_journal_paper_doi               10.1039/C5TA07173A
_journal_volume                  3
_journal_year                    2015
_chemical_formula_moiety         'C44 H22 F4 N8 O2 Si'
_chemical_formula_sum            'C44 H22 F4 N8 O2 Si'
_chemical_formula_weight         798.78
_chemical_name_systematic
'bis(3,5-difluorophenoxy) silicon phthalocyanine'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-09-03 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.453(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4484(6)
_cell_length_b                   13.6023(9)
_cell_length_c                   15.2391(10)
_cell_measurement_reflns_used    6440
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      66.32
_cell_measurement_theta_min      4.37
_cell_volume                     1736.4(2)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.981
_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  0.0238
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11884
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.519
_diffrn_reflns_theta_min         4.373
_diffrn_source                   'Bruker ImuS'
_exptl_absorpt_coefficient_mu    1.258
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0301
_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)+(0.0400P)²+0.7593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0792
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2721
_reflns_number_total             2992
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ta07173a2.cif
_cod_data_source_block           d1429_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7236116
_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   0.769
_shelx_estimated_absorpt_t_max   0.951
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.01604(14) Uani 1 2 d S . P
F1 F 0.66635(13) 0.72637(7) 0.20686(6) 0.0392(3) Uani 1 1 d . . .
F2 F 0.32304(12) 0.46817(7) 0.10455(6) 0.0394(2) Uani 1 1 d . . .
O1 O 0.56568(11) 0.46969(7) 0.40064(6) 0.0195(2) Uani 1 1 d . . .
N1 N 0.31801(13) 0.41629(8) 0.46910(7) 0.0184(2) Uani 1 1 d . . .
N2 N 0.12281(13) 0.53383(9) 0.40241(8) 0.0214(3) Uani 1 1 d . . .
N3 N 0.37832(13) 0.61014(8) 0.45235(7) 0.0176(2) Uani 1 1 d . . .
N4 N 0.57007(13) 0.74250(8) 0.48538(7) 0.0202(3) Uani 1 1 d . . .
C1 C 0.16904(16) 0.44489(10) 0.42925(9) 0.0191(3) Uani 1 1 d . . .
C2 C 0.22103(16) 0.60952(10) 0.41359(9) 0.0193(3) Uani 1 1 d . . .
C3 C 0.17140(16) 0.70810(11) 0.38739(9) 0.0213(3) Uani 1 1 d . . .
C4 C 0.02791(18) 0.74538(12) 0.34491(10) 0.0265(3) Uani 1 1 d . . .
H4A H -0.0599 0.7035 0.3261 0.032 Uiso 1 1 calc R U .
C5 C 0.01841(19) 0.84592(12) 0.33120(10) 0.0309(4) Uani 1 1 d . . .
H5A H -0.0778 0.8735 0.3022 0.037 Uiso 1 1 calc R U .
C6 C 0.14758(19) 0.90791(12) 0.35916(10) 0.0299(3) Uani 1 1 d . . .
H6A H 0.1369 0.9767 0.3492 0.036 Uiso 1 1 calc R U .
C7 C 0.29018(18) 0.87104(11) 0.40101(10) 0.0258(3) Uani 1 1 d . . .
H7A H 0.3778 0.9130 0.4201 0.031 Uiso 1 1 calc R U .
C8 C 0.30020(17) 0.76952(11) 0.41415(9) 0.0211(3) Uani 1 1 d . . .
C9 C 0.42841(16) 0.70706(10) 0.45400(9) 0.0185(3) Uani 1 1 d . . .
C10 C 0.68718(16) 0.68432(10) 0.51982(9) 0.0186(3) Uani 1 1 d . . .
C11 C 0.84560(16) 0.72065(11) 0.55171(9) 0.0203(3) Uani 1 1 d . . .
C12 C 0.91100(18) 0.81491(11) 0.55463(10) 0.0258(3) Uani 1 1 d . . .
H12A H 0.8499 0.8704 0.5327 0.031 Uiso 1 1 calc R U .
C13 C 1.06922(19) 0.82379(12) 0.59107(11) 0.0304(4) Uani 1 1 d . . .
H13A H 1.1175 0.8870 0.5949 0.037 Uiso 1 1 calc R U .
C14 C 1.15982(18) 0.74186(12) 0.62240(10) 0.0299(4) Uani 1 1 d . . .
H14A H 1.2682 0.7508 0.6467 0.036 Uiso 1 1 calc R U .
C15 C 1.09529(17) 0.64829(11) 0.61884(10) 0.0255(3) Uani 1 1 d . . .
H15A H 1.1568 0.5926 0.6398 0.031 Uiso 1 1 calc R U .
C16 C 0.93555(16) 0.63971(11) 0.58293(9) 0.0208(3) Uani 1 1 d . . .
C17 C 0.53896(16) 0.51373(10) 0.32087(9) 0.0185(3) Uani 1 1 d . . .
C18 C 0.61717(17) 0.60096(11) 0.30482(9) 0.0227(3) Uani 1 1 d . . .
H18A H 0.6865 0.6323 0.3505 0.027 Uiso 1 1 calc R U .
C19 C 0.59119(18) 0.64028(11) 0.22125(10) 0.0251(3) Uani 1 1 d . . .
C20 C 0.49481(18) 0.59853(11) 0.15163(10) 0.0268(3) Uani 1 1 d . . .
H20A H 0.4809 0.6268 0.0941 0.032 Uiso 1 1 calc R U .
C21 C 0.41979(18) 0.51275(11) 0.17113(10) 0.0256(3) Uani 1 1 d . . .
C22 C 0.43817(16) 0.46873(11) 0.25300(9) 0.0223(3) Uani 1 1 d . . .
H22A H 0.3838 0.4095 0.2630 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'
F F 0.0727 0.0534 '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 3_666 .
O1 Si1 N3 94.14(4) 3_666 3_666
O1 Si1 N3 85.86(4) . 3_666
O1 Si1 N3 85.86(4) 3_666 .
O1 Si1 N3 94.14(4) . .
N3 Si1 N3 180.0 3_666 .
O1 Si1 N1 88.94(4) 3_666 3_666
O1 Si1 N1 91.06(4) . 3_666
N3 Si1 N1 89.86(5) 3_666 3_666
N3 Si1 N1 90.14(5) . 3_666
O1 Si1 N1 91.06(4) 3_666 .
O1 Si1 N1 88.94(4) . .
N3 Si1 N1 90.14(5) 3_666 .
N3 Si1 N1 89.86(5) . .
N1 Si1 N1 180.0 3_666 .
C17 O1 Si1 130.46(8) . .
C10 N1 C1 106.96(11) 3_666 .
C10 N1 Si1 126.48(9) 3_666 .
C1 N1 Si1 126.54(9) . .
C2 N2 C1 121.29(12) . .
C2 N3 C9 106.76(11) . .
C2 N3 Si1 126.79(9) . .
C9 N3 Si1 126.38(9) . .
C9 N4 C10 121.45(12) . .
N2 C1 N1 127.65(12) . .
N2 C1 C16 122.52(13) . 3_666
N1 C1 C16 109.80(12) . 3_666
N2 C2 N3 127.84(13) . .
N2 C2 C3 122.21(12) . .
N3 C2 C3 109.92(12) . .
C8 C3 C4 121.20(14) . .
C8 C3 C2 106.77(12) . .
C4 C3 C2 132.02(14) . .
C5 C4 C3 117.35(15) . .
C5 C4 H4A 121.3 . .
C3 C4 H4A 121.3 . .
C4 C5 C6 121.41(15) . .
C4 C5 H5A 119.3 . .
C6 C5 H5A 119.3 . .
C7 C6 C5 121.32(14) . .
C7 C6 H6A 119.3 . .
C5 C6 H6A 119.3 . .
C6 C7 C8 117.26(15) . .
C6 C7 H7A 121.4 . .
C8 C7 H7A 121.4 . .
C3 C8 C7 121.44(14) . .
C3 C8 C9 106.56(12) . .
C7 C8 C9 132.00(14) . .
N4 C9 N3 127.94(13) . .
N4 C9 C8 122.11(13) . .
N3 C9 C8 109.95(12) . .
N4 C10 N1 127.47(12) . 3_666
N4 C10 C11 122.69(13) . .
N1 C10 C11 109.84(12) 3_666 .
C16 C11 C12 121.46(13) . .
C16 C11 C10 106.59(12) . .
C12 C11 C10 131.96(14) . .
C13 C12 C11 116.80(14) . .
C13 C12 H12A 121.6 . .
C11 C12 H12A 121.6 . .
C12 C13 C14 121.59(14) . .
C12 C13 H13A 119.2 . .
C14 C13 H13A 119.2 . .
C15 C14 C13 121.59(14) . .
C15 C14 H14A 119.2 . .
C13 C14 H14A 119.2 . .
C14 C15 C16 116.69(14) . .
C14 C15 H15A 121.7 . .
C16 C15 H15A 121.7 . .
C11 C16 C15 121.87(13) . .
C11 C16 C1 106.79(12) . 3_666
C15 C16 C1 131.34(14) . 3_666
O1 C17 C22 119.28(13) . .
O1 C17 C18 120.56(12) . .
C22 C17 C18 120.08(13) . .
C19 C18 C17 118.15(13) . .
C19 C18 H18A 120.9 . .
C17 C18 H18A 120.9 . .
F1 C19 C18 117.53(13) . .
F1 C19 C20 118.20(13) . .
C18 C19 C20 124.26(14) . .
C19 C20 C21 115.24(13) . .
C19 C20 H20A 122.4 . .
C21 C20 H20A 122.4 . .
F2 C21 C22 117.98(14) . .
F2 C21 C20 117.72(13) . .
C22 C21 C20 124.29(14) . .
C21 C22 C17 117.95(14) . .
C21 C22 H22A 121.0 . .
C17 C22 H22A 121.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 O1 1.7287(9) 3_666
Si1 O1 1.7287(9) .
Si1 N3 1.9066(11) 3_666
Si1 N3 1.9066(11) .
Si1 N1 1.9220(11) 3_666
Si1 N1 1.9221(11) .
F1 C19 1.3634(17) .
F2 C21 1.3602(17) .
O1 C17 1.3477(16) .
N1 C10 1.3803(18) 3_666
N1 C1 1.3806(18) .
N2 C2 1.3194(18) .
N2 C1 1.3198(19) .
N3 C2 1.3824(18) .
N3 C9 1.3839(18) .
N4 C9 1.3210(18) .
N4 C10 1.3213(18) .
C1 C16 1.4481(19) 3_666
C2 C3 1.446(2) .
C3 C8 1.390(2) .
C3 C4 1.394(2) .
C4 C5 1.384(2) .
C4 H4A 0.9500 .
C5 C6 1.401(2) .
C5 H5A 0.9500 .
C6 C7 1.382(2) .
C6 H6A 0.9500 .
C7 C8 1.396(2) .
C7 H7A 0.9500 .
C8 C9 1.447(2) .
C10 N1 1.3803(18) 3_666
C10 C11 1.4501(19) .
C11 C16 1.386(2) .
C11 C12 1.395(2) .
C12 C13 1.385(2) .
C12 H12A 0.9500 .
C13 C14 1.400(2) .
C13 H13A 0.9500 .
C14 C15 1.383(2) .
C14 H14A 0.9500 .
C15 C16 1.394(2) .
C15 H15A 0.9500 .
C16 C1 1.4481(19) 3_666
C17 C22 1.393(2) .
C17 C18 1.395(2) .
C18 C19 1.372(2) .
C18 H18A 0.9500 .
C19 C20 1.374(2) .
C20 C21 1.379(2) .
C20 H20A 0.9500 .
C21 C22 1.374(2) .
C22 H22A 0.9500 .
