#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:07:04 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180412 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/81/7208134.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_7208134
loop_
_publ_author_name
'Chien, Ching-Ting'
'Lin, Chih-Chun'
'Watanabe, Motonori'
'Lin, Yan-Duo'
'Chao, Ting-Han'
'Chiang, Ta-chung'
'Huang, Xin-Hua'
'Wen, Yuh-Sheng'
'Tu, Chih-Hsin'
'Sun, Chia-Hsing'
'Chow, Tahsin J.'
_publ_section_title
;
 Tetracene-based field-effect transistors using solution processes
;
_journal_issue                   26
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              13070
_journal_paper_doi               10.1039/c2jm31134h
_journal_volume                  22
_journal_year                    2012
_chemical_formula_moiety         'C22 H18 O2'
_chemical_formula_sum            'C22 H18 O2'
_chemical_formula_weight         314.36
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                102.711(2)
_cell_angle_beta                 102.324(2)
_cell_angle_gamma                91.986(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1278(4)
_cell_length_b                   9.4651(4)
_cell_length_c                   10.7576(5)
_cell_measurement_reflns_used    5395
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      2.57
_cell_volume                     785.80(6)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11193
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.04
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0448P)²+0.3123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.096
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                2780
_reflns_number_total             3194
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2jm31134h.txt
_cod_data_source_block           i12160
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/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_values 1891 2012-01-12 08:04:46Z andrius 

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      P-1
_cod_database_code               7208134
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.28652(12) 0.59164(10) 0.44155(9) 0.0269(2) Uani 1 1 d .
O2 O 0.48916(14) 1.08945(10) 0.80994(10) 0.0310(3) Uani 1 1 d .
C1 C 0.18718(16) 0.84623(13) 0.90421(12) 0.0192(3) Uani 1 1 d .
H1 H 0.2173 0.9332 0.967 0.023 Uiso 1 1 calc R
C2 C 0.02009(16) 0.78668(14) 0.86355(13) 0.0218(3) Uani 1 1 d .
H2 H -0.0621 0.8334 0.9014 0.026 Uiso 1 1 calc R
C3 C -0.02574(16) 0.65876(15) 0.76747(13) 0.0217(3) Uani 1 1 d .
H3 H -0.1382 0.6212 0.7417 0.026 Uiso 1 1 calc R
C4 C 0.09435(16) 0.58573(14) 0.70910(12) 0.0194(3) Uani 1 1 d .
H4 H 0.0632 0.5013 0.6432 0.023 Uiso 1 1 calc R
C4A C 0.26131(15) 0.64245(13) 0.75210(12) 0.0171(3) Uani 1 1 d .
C5 C 0.42317(15) 0.59007(13) 0.71633(12) 0.0172(3) Uani 1 1 d .
H5 H 0.4204 0.4864 0.6755 0.021 Uiso 1 1 calc R
C5A C 0.48097(15) 0.69928(13) 0.63994(12) 0.0172(3) Uani 1 1 d .
H5A H 0.5816 0.6651 0.6103 0.021 Uiso 1 1 calc R
C6 C 0.34586(16) 0.70423(14) 0.52102(12) 0.0187(3) Uani 1 1 d .
C6A C 0.28687(16) 0.84683(14) 0.50087(12) 0.0195(3) Uani 1 1 d .
C7 C 0.17428(17) 0.84992(16) 0.38349(13) 0.0247(3) Uani 1 1 d .
H7 H 0.1379 0.7643 0.32 0.03 Uiso 1 1 calc R
C8 C 0.11708(18) 0.98016(17) 0.36183(14) 0.0293(3) Uani 1 1 d .
H8 H 0.043 0.9819 0.2834 0.035 Uiso 1 1 calc R
C9 C 0.16973(18) 1.10845(16) 0.45665(15) 0.0291(3) Uani 1 1 d .
H9 H 0.1307 1.1957 0.4415 0.035 Uiso 1 1 calc R
C10 C 0.27994(18) 1.10664(15) 0.57323(14) 0.0252(3) Uani 1 1 d .
H10 H 0.3144 1.1927 0.6366 0.03 Uiso 1 1 calc R
C10A C 0.33985(16) 0.97595(14) 0.59635(12) 0.0198(3) Uani 1 1 d .
C11 C 0.45650(16) 0.97851(13) 0.72407(12) 0.0198(3) Uani 1 1 d .
C11A C 0.53550(15) 0.84208(13) 0.74759(12) 0.0174(3) Uani 1 1 d .
H11A H 0.6583 0.861 0.7623 0.021 Uiso 1 1 calc R
C12 C 0.49689(15) 0.80086(13) 0.87293(12) 0.0167(3) Uani 1 1 d .
H12 H 0.5527 0.8652 0.9571 0.02 Uiso 1 1 calc R
C12A C 0.30702(15) 0.77209(13) 0.84830(12) 0.0164(3) Uani 1 1 d .
C13 C 0.54531(15) 0.64480(13) 0.84930(12) 0.0170(3) Uani 1 1 d .
C14 C 0.65460(16) 0.57842(14) 0.92279(12) 0.0193(3) Uani 1 1 d .
C15 C 0.68376(18) 0.42116(14) 0.88068(14) 0.0248(3) Uani 1 1 d .
H15A H 0.6187 0.382 0.7933 0.037 Uiso 1 1 calc R
H15B H 0.6497 0.3684 0.939 0.037 Uiso 1 1 calc R
H15C H 0.8016 0.4125 0.8828 0.037 Uiso 1 1 calc R
C16 C 0.75760(17) 0.65496(15) 1.05578(13) 0.0248(3) Uani 1 1 d .
H16A H 0.7328 0.7548 1.0748 0.037 Uiso 1 1 calc R
H16B H 0.8757 0.6502 1.0568 0.037 Uiso 1 1 calc R
H16C H 0.73 0.6087 1.1206 0.037 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
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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
C12A C1 C2 117.97(12)
C12A C1 H1 121
C2 C1 H1 121
C3 C2 C1 121.06(12)
C3 C2 H2 119.5
C1 C2 H2 119.5
C2 C3 C4 120.96(12)
C2 C3 H3 119.5
C4 C3 H3 119.5
C4A C4 C3 118.06(12)
C4A C4 H4 121
C3 C4 H4 121
C4 C4A C12A 120.84(11)
C4 C4A C5 132.45(11)
C12A C4A C5 106.70(10)
C4A C5 C13 99.24(9)
C4A C5 C5A 105.82(9)
C13 C5 C5A 100.05(9)
C4A C5 H5 116.4
C13 C5 H5 116.4
C5A C5 H5 116.4
C6 C5A C11A 117.80(10)
C6 C5A C5 111.21(10)
C11A C5A C5 103.22(9)
C6 C5A H5A 108.1
C11A C5A H5A 108.1
C5 C5A H5A 108.1
O1 C6 C6A 120.50(12)
O1 C6 C5A 119.67(11)
C6A C6 C5A 119.83(11)
C10A C6A C7 119.63(12)
C10A C6A C6 121.76(11)
C7 C6A C6 118.61(12)
C8 C7 C6A 120.05(13)
C8 C7 H7 120
C6A C7 H7 120
C7 C8 C9 120.33(13)
C7 C8 H8 119.8
C9 C8 H8 119.8
C10 C9 C8 120.15(13)
C10 C9 H9 119.9
C8 C9 H9 119.9
C9 C10 C10A 120.24(13)
C9 C10 H10 119.9
C10A C10 H10 119.9
C10 C10A C6A 119.60(12)
C10 C10A C11 118.51(12)
C6A C10A C11 121.88(11)
O2 C11 C10A 120.75(12)
O2 C11 C11A 119.43(12)
C10A C11 C11A 119.82(11)
C11 C11A C5A 118.18(10)
C11 C11A C12 111.65(10)
C5A C11A C12 103.34(9)
C11 C11A H11A 107.7
C5A C11A H11A 107.7
C12 C11A H11A 107.7
C12A C12 C13 99.38(9)
C12A C12 C11A 106.95(9)
C13 C12 C11A 99.27(9)
C12A C12 H12 116.2
C13 C12 H12 116.2
C11A C12 H12 116.2
C1 C12A C4A 121.06(11)
C1 C12A C12 131.99(11)
C4A C12A C12 106.93(10)
C14 C13 C12 131.24(12)
C14 C13 C5 132.15(12)
C12 C13 C5 96.59(9)
C13 C14 C15 122.82(12)
C13 C14 C16 122.52(12)
C15 C14 C16 114.66(11)
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.2193(16)
O2 C11 1.2147(16)
C1 C12A 1.3837(17)
C1 C2 1.3922(18)
C1 H1 0.93
C2 C3 1.3881(19)
C2 H2 0.93
C3 C4 1.3936(18)
C3 H3 0.93
C4 C4A 1.3842(18)
C4 H4 0.93
C4A C12A 1.4000(17)
C4A C5 1.5172(17)
C5 C13 1.5271(17)
C5 C5A 1.5714(17)
C5 H5 0.98
C5A C6 1.5083(17)
C5A C11A 1.5540(16)
C5A H5A 0.98
C6 C6A 1.4926(17)
C6A C10A 1.3987(18)
C6A C7 1.3991(18)
C7 C8 1.382(2)
C7 H7 0.93
C8 C9 1.389(2)
C8 H8 0.93
C9 C10 1.381(2)
C9 H9 0.93
C10 C10A 1.3980(18)
C10 H10 0.93
C10A C11 1.4883(18)
C11 C11A 1.5085(17)
C11A C12 1.5725(17)
C11A H11A 0.98
C12 C12A 1.5135(17)
C12 C13 1.5228(17)
C12 H12 0.98
C13 C14 1.3290(18)
C14 C15 1.5002(18)
C14 C16 1.5043(18)
C15 H15A 0.96
C15 H15B 0.96
C15 H15C 0.96
C16 H16A 0.96
C16 H16B 0.96
C16 H16C 0.96
