#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:05:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180373 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/42/7204262.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_7204262
loop_
_publ_author_name
'Christopher Farren'
'Simon FitzGerald'
'Martin R. Bryce'
'Andrew Beeby'
'Andrei S. Batsanov'
_publ_section_title
;
 Synthesis, structure and optical characterisation of silicon
 phthalocyanine bis-esters
;
_journal_issue                   1
_journal_name_full               'J. Chem. Soc., Perkin Trans. 2'
_journal_page_first              59
_journal_page_last               66
_journal_paper_doi               10.1039/b108778a
_journal_year                    2002
_chemical_formula_sum            'C54 H42 N8 O4 Si'
_chemical_formula_weight         895.05
_chemical_name_systematic
' silicon phthalocyanine di(p-t-butylbenzoic acid)   '
_space_group_IT_number           148
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                120.00
_cell_formula_units_Z            9
_cell_length_a                   36.327(8)
_cell_length_b                   36.327(8)
_cell_length_c                   8.841(2)
_cell_measurement_reflns_used    680
_cell_measurement_temperature    108(2)
_cell_measurement_theta_max      21.1
_cell_measurement_theta_min      12.0
_cell_volume                     10104(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      108(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SMART 1K CCD area detector'
_diffrn_measurement_method       'ω scans'
_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  0.0820
_diffrn_reflns_av_sigmaI/netI    0.0775
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20515
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue-purple
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             4212
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0463P)²+7.2208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1166
_reflns_number_gt                3259
_reflns_number_total             5166
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b108778a.txt
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Rhombohedral' changed to 'rhombohedral'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               7204262
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si Si 0.5000 0.0000 1.0000 0.01381(18) Uani 1 2 d S . .
O1 O 0.50651(4) 0.04731(4) 0.92219(16) 0.0157(3) Uani 1 1 d . . .
O2 O 0.44440(5) 0.04672(5) 0.94182(18) 0.0226(4) Uani 1 1 d . . .
N1 N 0.45100(5) -0.03527(5) 0.87964(19) 0.0151(4) Uani 1 1 d . . .
N2 N 0.48356(5) -0.04371(5) 0.6516(2) 0.0167(4) Uani 1 1 d . . .
N3 N 0.53574(5) 0.00134(5) 0.83931(19) 0.0145(4) Uani 1 1 d . . .
N4 N 0.60584(5) 0.04878(5) 0.94371(19) 0.0160(4) Uani 1 1 d . . .
C1 C 0.40871(6) -0.05394(6) 0.9255(2) 0.0150(4) Uani 1 1 d . . .
C2 C 0.45068(6) -0.05199(6) 0.7385(2) 0.0150(4) Uani 1 1 d . . .
C3 C 0.52282(6) -0.01813(6) 0.6990(2) 0.0149(4) Uani 1 1 d . . .
C4 C 0.57986(6) 0.02434(6) 0.8364(2) 0.0156(4) Uani 1 1 d . . .
C5 C 0.38128(7) -0.08239(6) 0.8097(2) 0.0165(4) Uani 1 1 d . . .
C6 C 0.33704(7) -0.10759(7) 0.7999(3) 0.0199(5) Uani 1 1 d . . .
H6 H 0.3191 -0.1081 0.8791 0.024 Uiso 1 1 d R . .
C7 C 0.32042(7) -0.13181(7) 0.6705(3) 0.0236(5) Uani 1 1 d . . .
H7 H 0.2904 -0.1492 0.6608 0.028 Uiso 1 1 d R . .
C8 C 0.34684(7) -0.13119(7) 0.5533(3) 0.0235(5) Uani 1 1 d . . .
H8 H 0.3344 -0.1484 0.4664 0.028 Uiso 1 1 d R . .
C9 C 0.39066(7) -0.10602(7) 0.5620(2) 0.0208(5) Uani 1 1 d . . .
H9 H 0.4086 -0.1055 0.4828 0.025 Uiso 1 1 d R . .
C10 C 0.40736(7) -0.08144(7) 0.6922(2) 0.0170(5) Uani 1 1 d . . .
C11 C 0.55947(6) -0.00711(6) 0.6048(2) 0.0156(4) Uani 1 1 d . . .
C12 C 0.56287(7) -0.01798(7) 0.4554(2) 0.0183(5) Uani 1 1 d . . .
H12 H 0.5383 -0.0355 0.3965 0.022 Uiso 1 1 d R . .
C13 C 0.60342(7) -0.00209(7) 0.3972(3) 0.0210(5) Uani 1 1 d . . .
H13 H 0.6069 -0.0092 0.2968 0.025 Uiso 1 1 d R . .
C14 C 0.63960(7) 0.02426(7) 0.4846(3) 0.0212(5) Uani 1 1 d . . .
H14 H 0.6670 0.0347 0.4414 0.025 Uiso 1 1 d R . .
C15 C 0.63616(7) 0.03553(7) 0.6318(3) 0.0185(5) Uani 1 1 d . . .
H15 H 0.6606 0.0534 0.6904 0.022 Uiso 1 1 d R . .
C16 C 0.59520(6) 0.01928(6) 0.6906(2) 0.0154(4) Uani 1 1 d . . .
C17 C 0.48158(7) 0.06405(6) 0.9053(2) 0.0150(4) Uani 1 1 d . . .
C18 C 0.50418(6) 0.10694(6) 0.8300(2) 0.0160(4) Uani 1 1 d . . .
C19 C 0.54402(7) 0.12247(7) 0.7634(3) 0.0215(5) Uani 1 1 d . . .
H19 H 0.5581 0.1064 0.7687 0.026 Uiso 1 1 d R . .
C20 C 0.56308(7) 0.16132(7) 0.6890(3) 0.0241(5) Uani 1 1 d . . .
H20 H 0.5901 0.1713 0.6431 0.029 Uiso 1 1 d R . .
C21 C 0.54382(7) 0.18633(7) 0.6798(2) 0.0187(5) Uani 1 1 d . . .
C22 C 0.50442(7) 0.17054(7) 0.7499(2) 0.0208(5) Uani 1 1 d . . .
H22 H 0.4908 0.1871 0.7483 0.025 Uiso 1 1 d R . .
C23 C 0.48438(7) 0.13129(7) 0.8221(2) 0.0184(5) Uani 1 1 d . . .
H23 H 0.4571 0.1210 0.8661 0.022 Uiso 1 1 d R . .
C24 C 0.56584(7) 0.22865(7) 0.5930(3) 0.0232(5) Uani 1 1 d . . .
C25 C 0.57107(8) 0.21974(8) 0.4266(3) 0.0329(6) Uani 1 1 d . . .
H25A H 0.5871 0.2046 0.4211 0.038(4) Uiso 1 1 d R . .
H25B H 0.5865 0.2467 0.3717 0.038(4) Uiso 1 1 d R . .
H25C H 0.5429 0.2022 0.3809 0.038(4) Uiso 1 1 d R . .
C26 C 0.54054(8) 0.25197(8) 0.5992(3) 0.0313(6) Uani 1 1 d . . .
H26A H 0.5123 0.2338 0.5553 0.033(4) Uiso 1 1 d R . .
H26B H 0.5555 0.2785 0.5415 0.033(4) Uiso 1 1 d R . .
H26C H 0.5375 0.2584 0.7046 0.033(4) Uiso 1 1 d R . .
C27 C 0.61036(8) 0.25778(7) 0.6615(3) 0.0329(6) Uani 1 1 d . . .
H27A H 0.6076 0.2621 0.7694 0.038(4) Uiso 1 1 d R . .
H27B H 0.6239 0.2853 0.6093 0.038(4) Uiso 1 1 d R . .
H27C H 0.6279 0.2444 0.6492 0.038(4) Uiso 1 1 d R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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
_geom_angle_publ_flag
O1 Si O1 180.00(4) . 10_657 ?
O1 Si N3 85.78(7) . . ?
O1 Si N3 94.22(7) 10_657 . ?
O1 Si N3 94.22(7) . 10_657 ?
O1 Si N3 85.78(7) 10_657 10_657 ?
N3 Si N3 180.00(8) . 10_657 ?
O1 Si N1 93.58(7) . . ?
O1 Si N1 86.42(7) 10_657 . ?
N3 Si N1 89.79(7) . . ?
N3 Si N1 90.21(7) 10_657 . ?
O1 Si N1 86.42(7) . 10_657 ?
O1 Si N1 93.58(7) 10_657 10_657 ?
N3 Si N1 90.21(7) . 10_657 ?
N3 Si N1 89.79(7) 10_657 10_657 ?
N1 Si N1 180.00(9) . 10_657 ?
C17 O1 Si 134.76(13) . . ?
C2 N1 C1 106.44(16) . . ?
C2 N1 Si 126.54(13) . . ?
C1 N1 Si 126.45(14) . . ?
C3 N2 C2 120.66(18) . . ?
C3 N3 C4 106.51(17) . . ?
C3 N3 Si 126.86(14) . . ?
C4 N3 Si 126.51(14) . . ?
C4 N4 C1 121.45(18) . 10_657 ?
N4 C1 N1 127.33(19) 10_657 . ?
N4 C1 C5 122.70(18) 10_657 . ?
N1 C1 C5 109.93(17) . . ?
N2 C2 N1 127.98(18) . . ?
N2 C2 C10 121.78(19) . . ?
N1 C2 C10 110.24(17) . . ?
N2 C3 N3 127.75(19) . . ?
N2 C3 C11 122.15(19) . . ?
N3 C3 C11 110.09(17) . . ?
N4 C4 N3 127.83(19) . . ?
N4 C4 C16 122.19(18) . . ?
N3 C4 C16 109.95(18) . . ?
C10 C5 C6 120.9(2) . . ?
C10 C5 C1 107.08(18) . . ?
C6 C5 C1 132.0(2) . . ?
C7 C6 C5 117.4(2) . . ?
C6 C7 C8 121.5(2) . . ?
C9 C8 C7 121.3(2) . . ?
C8 C9 C10 117.2(2) . . ?
C5 C10 C9 121.7(2) . . ?
C5 C10 C2 106.30(18) . . ?
C9 C10 C2 132.0(2) . . ?
C16 C11 C12 121.64(19) . . ?
C16 C11 C3 106.83(18) . . ?
C12 C11 C3 131.5(2) . . ?
C13 C12 C11 117.3(2) . . ?
C12 C13 C14 121.1(2) . . ?
C15 C14 C13 121.6(2) . . ?
C14 C15 C16 117.2(2) . . ?
C11 C16 C15 121.2(2) . . ?
C11 C16 C4 106.62(18) . . ?
C15 C16 C4 132.2(2) . . ?
O2 C17 O1 124.70(19) . . ?
O2 C17 C18 122.94(18) . . ?
O1 C17 C18 112.33(17) . . ?
C23 C18 C19 118.88(19) . . ?
C23 C18 C17 119.48(19) . . ?
C19 C18 C17 121.61(18) . . ?
C20 C19 C18 120.0(2) . . ?
C19 C20 C21 122.1(2) . . ?
C22 C21 C20 116.8(2) . . ?
C22 C21 C24 123.20(19) . . ?
C20 C21 C24 120.0(2) . . ?
C23 C22 C21 121.99(19) . . ?
C22 C23 C18 120.2(2) . . ?
C26 C24 C21 112.29(19) . . ?
C26 C24 C25 108.8(2) . . ?
C21 C24 C25 108.91(18) . . ?
C26 C24 C27 108.63(19) . . ?
C21 C24 C27 109.40(19) . . ?
C25 C24 C27 108.8(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si O1 1.7540(14) . ?
Si O1 1.7540(14) 10_657 ?
Si N3 1.9087(17) . ?
Si N3 1.9087(17) 10_657 ?
Si N1 1.9136(17) . ?
Si N1 1.9136(17) 10_657 ?
O1 C17 1.328(2) . ?
O2 C17 1.214(2) . ?
N1 C2 1.385(3) . ?
N1 C1 1.393(2) . ?
N2 C3 1.322(3) . ?
N2 C2 1.322(3) . ?
N3 C3 1.388(3) . ?
N3 C4 1.389(3) . ?
N4 C4 1.320(3) . ?
N4 C1 1.323(3) 10_657 ?
C1 N4 1.323(3) 10_657 ?
C1 C5 1.442(3) . ?
C2 C10 1.451(3) . ?
C3 C11 1.447(3) . ?
C4 C16 1.452(3) . ?
C5 C10 1.395(3) . ?
C5 C6 1.399(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.405(3) . ?
C8 C9 1.386(3) . ?
C9 C10 1.396(3) . ?
C11 C16 1.391(3) . ?
C11 C12 1.402(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.408(3) . ?
C14 C15 1.389(3) . ?
C15 C16 1.398(3) . ?
C17 C18 1.505(3) . ?
C18 C23 1.393(3) . ?
C18 C19 1.394(3) . ?
C19 C20 1.388(3) . ?
C20 C21 1.399(3) . ?
C21 C22 1.393(3) . ?
C21 C24 1.537(3) . ?
C22 C23 1.390(3) . ?
C24 C26 1.531(3) . ?
C24 C25 1.539(3) . ?
C24 C27 1.546(3) . ?
