#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:51:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180452 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/21/7212124.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_7212124
loop_
_publ_author_name
'Wöbkenberg, Paul H.'
'Labram, John G.'
'Swiecicki, Jean-Marie'
'Parkhomenko, Ksenia'
'Sredojevic, Dusan'
'Gisselbrecht, Jean-Paul'
'de Leeuw, Dago M.'
'Bradley, Donal D. C.'
'Djukic, Jean-Pierre'
'Anthopoulos, Thomas D.'
_publ_section_title
;
 Ambipolar organic transistors and near-infrared phototransistors based on
 a solution-processable squarilium dye
;
_journal_issue                   18
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              3673
_journal_paper_doi               10.1039/b919970e
_journal_volume                  20
_journal_year                    2010
_chemical_formula_moiety         'C34 H34 O2'
_chemical_formula_sum            'C34 H34 O2'
_chemical_formula_weight         474.61
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 123.306(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6702(6)
_cell_length_b                   14.2059(10)
_cell_length_c                   11.0365(7)
_cell_measurement_reflns_used    6269
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1267.10(15)
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega 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  0.0653
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10136
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0560
_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/[σ2^(Fo2^)+(0.0716P)2^+0.0000P] where P=(Fo2+2Fc2)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1373
_reflns_number_gt                1850
_reflns_number_total             2894
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b919970e.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1267.10(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7212124
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O -0.22207(15) 0.01974(9) 0.14165(11) 0.0341(4) Uani 1 1 d .
C1 C -0.3728(2) 0.00960(12) 0.06683(17) 0.0256(4) Uani 1 1 d .
C2 C -0.5023(2) -0.02241(12) 0.08910(16) 0.0243(4) Uani 1 1 d .
C3 C -0.5263(2) -0.06057(12) 0.19476(17) 0.0238(4) Uani 1 1 d .
C4 C -0.6709(2) -0.11528(12) 0.15115(17) 0.0259(4) Uani 1 1 d .
H4 H -0.7629 -0.1211 0.0538 0.031 Uiso 1 1 calc R
C5 C -0.6598(2) -0.15806(12) 0.26717(17) 0.0250(4) Uani 1 1 d .
C6 C -0.7872(2) -0.21977(13) 0.26426(18) 0.0336(5) Uani 1 1 d .
H6A H -0.8743 -0.2345 0.1635 0.050 Uiso 1 1 calc R
H6B H -0.8356 -0.1870 0.3105 0.050 Uiso 1 1 calc R
H6C H -0.7349 -0.2783 0.3168 0.050 Uiso 1 1 calc R
C7 C -0.5049(2) -0.13177(12) 0.39444(16) 0.0236(4) Uani 1 1 d .
C8 C -0.4223(2) -0.06549(12) 0.35146(17) 0.0234(4) Uani 1 1 d .
C9 C -0.2872(2) -0.00924(12) 0.44664(17) 0.0255(4) Uani 1 1 d .
C10 C -0.2476(2) 0.07556(13) 0.38981(18) 0.0332(5) Uani 1 1 d .
H10A H -0.1761 0.0569 0.3566 0.050 Uiso 1 1 calc R
H10B H -0.1905 0.1225 0.4671 0.050 Uiso 1 1 calc R
H10C H -0.3504 0.1026 0.3086 0.050 Uiso 1 1 calc R
C11 C -0.1800(2) -0.02436(13) 0.59677(16) 0.0308(4) Uani 1 1 d .
H11 H -0.0893 0.0181 0.6436 0.037 Uiso 1 1 calc R
C12 C -0.1823(2) -0.08971(13) 0.68900(18) 0.0323(5) Uani 1 1 d .
H12 H -0.0861 -0.0899 0.7848 0.039 Uiso 1 1 calc R
C13 C -0.3030(2) -0.15540(12) 0.66404(17) 0.0265(4) Uani 1 1 d .
C14 C -0.4496(2) -0.16898(12) 0.53096(16) 0.0263(4) Uani 1 1 d .
H14 H -0.5253 -0.2106 0.5328 0.032 Uiso 1 1 calc R
C15 C -0.2706(2) -0.21686(13) 0.79097(17) 0.0310(5) Uani 1 1 d .
H15 H -0.3738 -0.2536 0.7577 0.037 Uiso 1 1 calc R
C16 C -0.2318(3) -0.16013(15) 0.92275(19) 0.0466(6) Uani 1 1 d .
H16A H -0.1302 -0.1239 0.9589 0.070 Uiso 1 1 calc R
H16B H -0.2167 -0.2029 0.9988 0.070 Uiso 1 1 calc R
H16C H -0.3236 -0.1170 0.8956 0.070 Uiso 1 1 calc R
C17 C -0.1330(2) -0.28731(13) 0.83179(19) 0.0381(5) Uani 1 1 d .
H17A H -0.1636 -0.3265 0.7475 0.057 Uiso 1 1 calc R
H17B H -0.1164 -0.3273 0.9111 0.057 Uiso 1 1 calc R
H17C H -0.0303 -0.2534 0.8631 0.057 Uiso 1 1 calc 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'
O O 0.0106 0.0060 '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 C1 C2 132.88(15) . 3_455
O1 C1 C2 136.72(15) . .
C2 C1 C2 90.36(13) 3_455 .
C3 C2 C1 127.54(16) . 3_455
C3 C2 C1 142.54(16) . .
C1 C2 C1 89.64(13) 3_455 .
C2 C3 C4 120.14(14) . .
C2 C3 C8 132.97(16) . .
C4 C3 C8 106.55(13) . .
C5 C4 C3 111.51(14) . .
C5 C4 H4 124.2 . .
C3 C4 H4 124.2 . .
C4 C5 C7 107.73(15) . .
C4 C5 C6 126.85(16) . .
C7 C5 C6 125.41(15) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C14 C7 C5 122.32(16) . .
C14 C7 C8 129.47(15) . .
C5 C7 C8 108.17(14) . .
C9 C8 C3 128.42(15) . .
C9 C8 C7 125.04(14) . .
C3 C8 C7 105.77(14) . .
C8 C9 C11 125.42(16) . .
C8 C9 C10 119.59(14) . .
C11 C9 C10 114.99(15) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C12 C11 C9 131.94(17) . .
C12 C11 H11 114.0 . .
C9 C11 H11 114.0 . .
C11 C12 C13 130.53(16) . .
C11 C12 H12 114.7 . .
C13 C12 H12 114.7 . .
C14 C13 C12 124.02(15) . .
C14 C13 C15 117.88(16) . .
C12 C13 C15 118.10(15) . .
C13 C14 C7 130.85(17) . .
C13 C14 H14 114.6 . .
C7 C14 H14 114.6 . .
C16 C15 C17 110.46(14) . .
C16 C15 C13 113.12(15) . .
C17 C15 C13 110.66(14) . .
C16 C15 H15 107.4 . .
C17 C15 H15 107.4 . .
C13 C15 H15 107.4 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C15 C17 H17A 109.5 . .
C15 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C15 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2269(19) .
C1 C2 1.473(2) 3_455
C1 C2 1.474(2) .
C2 C3 1.416(2) .
C2 C1 1.473(2) 3_455
C3 C4 1.432(2) .
C3 C8 1.448(2) .
C4 C5 1.368(2) .
C4 H4 0.9500 .
C5 C7 1.430(2) .
C5 C6 1.497(2) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C14 1.397(2) .
C7 C8 1.472(2) .
C8 C9 1.393(2) .
C9 C11 1.407(2) .
C9 C10 1.502(2) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C12 1.387(2) .
C11 H11 0.9500 .
C12 C13 1.399(2) .
C12 H12 0.9500 .
C13 C14 1.385(2) .
C13 C15 1.530(2) .
C14 H14 0.9500 .
C15 C16 1.519(2) .
C15 C17 1.522(3) .
C15 H15 1.0000 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
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
O1 C1 C2 C3 -4.3(4) . .
C2 C1 C2 C3 173.5(3) 3_455 .
O1 C1 C2 C1 -177.9(3) . 3_455
C2 C1 C2 C1 0.0 3_455 3_455
C1 C2 C3 C4 17.4(3) 3_455 .
C1 C2 C3 C4 -154.4(2) . .
C1 C2 C3 C8 -170.28(17) 3_455 .
C1 C2 C3 C8 17.9(4) . .
C2 C3 C4 C5 170.44(15) . .
C8 C3 C4 C5 -3.71(19) . .
C3 C4 C5 C7 0.6(2) . .
C3 C4 C5 C6 179.32(16) . .
C4 C5 C7 C14 -175.30(15) . .
C6 C5 C7 C14 5.9(3) . .
C4 C5 C7 C8 2.76(19) . .
C6 C5 C7 C8 -176.00(16) . .
C2 C3 C8 C9 21.8(3) . .
C4 C3 C8 C9 -165.08(17) . .
C2 C3 C8 C7 -167.93(18) . .
C4 C3 C8 C7 5.15(18) . .
C14 C7 C8 C9 -16.4(3) . .
C5 C7 C8 C9 165.72(16) . .
C14 C7 C8 C3 172.94(16) . .
C5 C7 C8 C3 -4.93(18) . .
C3 C8 C9 C11 -172.49(17) . .
C7 C8 C9 C11 19.0(3) . .
C3 C8 C9 C10 7.7(3) . .
C7 C8 C9 C10 -160.80(16) . .
C8 C9 C11 C12 -4.7(3) . .
C10 C9 C11 C12 175.08(19) . .
C9 C11 C12 C13 -8.0(3) . .
C11 C12 C13 C14 2.4(3) . .
C11 C12 C13 C15 -178.34(18) . .
C12 C13 C14 C7 7.0(3) . .
C15 C13 C14 C7 -172.24(17) . .
C5 C7 C14 C13 177.21(17) . .
C8 C7 C14 C13 -0.4(3) . .
C14 C13 C15 C16 -125.90(18) . .
C12 C13 C15 C16 54.8(2) . .
C14 C13 C15 C17 109.55(18) . .
C12 C13 C15 C17 -69.8(2) . .
