#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/34/7103409.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_7103409
loop_
_publ_author_name
'Hirao, Atsuko'
'Akiyama, Taiji'
'Okujima, Tetsuo'
'Yamada, Hiroko'
'Uno, Hidemitsu'
'Sakai, Yoshimasa'
'Aramaki, Shinji'
'Ono, Noboru'
_publ_section_title
;
 Soluble precursors of 2,3-naphthalocyanine and phthalocyanine for use
 in thin film transistors.
;
_journal_issue                   39
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4714
_journal_page_last               4716
_journal_paper_doi               10.1039/b811674a
_journal_year                    2008
_chemical_formula_moiety         'C13 H12 N2 O2 '
_chemical_formula_sum            'C13 H12 N2 O2'
_chemical_formula_weight         228.25
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                114.705(17)
_cell_angle_beta                 95.44(2)
_cell_angle_gamma                102.56(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7368(14)
_cell_length_b                   9.5154(15)
_cell_length_c                   10.4950(15)
_cell_measurement_reflns_used    1327
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     583.3(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8.2'
_computing_structure_refinement  SHELXL97
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 14.6199
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku Mercury-8'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6098
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0782
_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)+(0.1397P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2034
_refine_ls_wR_factor_ref         0.2465
_reflns_number_gt                1445
_reflns_number_total             2639
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b811674a.txt
_cod_data_source_block           '__LessPolar'
_cod_original_formula_sum        'C13 H12 N2 O2 '
_cod_database_code               7103409
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6777(3) 0.3559(2) 0.41162(18) 0.0645(6) Uani 1 1 d . . .
O2 O 0.5461(4) 0.1221(2) 0.20717(19) 0.0713(7) Uani 1 1 d . . .
N1 N 0.6312(4) 0.3535(4) -0.2136(3) 0.0836(9) Uani 1 1 d . . .
N2 N 0.8841(5) 0.7960(4) 0.1585(4) 0.0935(10) Uani 1 1 d . . .
C1 C 0.5648(5) 0.1891(3) 0.3584(3) 0.0584(7) Uani 1 1 d . . .
C2 C 0.6467(4) 0.4030(3) 0.3006(3) 0.0540(7) Uani 1 1 d . . .
H2 H 0.5477 0.4673 0.3169 0.065 Uiso 1 1 calc R . .
C3 C 0.8591(4) 0.4977(3) 0.2911(3) 0.0564(7) Uani 1 1 d . . .
H3 H 0.9193 0.6012 0.3769 0.068 Uiso 1 1 calc R . .
C4 C 0.8127(4) 0.5189(3) 0.1576(3) 0.0535(7) Uani 1 1 d . . .
C5 C 0.7396(4) 0.3788(3) 0.0375(3) 0.0535(7) Uani 1 1 d . . .
C6 C 0.7199(4) 0.2315(3) 0.0625(3) 0.0587(7) Uani 1 1 d . . .
H6 H 0.6745 0.1306 -0.0268 0.070 Uiso 1 1 calc R . .
C7 C 0.5621(4) 0.2443(3) 0.1630(3) 0.0570(7) Uani 1 1 d . . .
H7 H 0.4258 0.2374 0.1149 0.068 Uiso 1 1 calc R . .
C8 C 0.9250(5) 0.2517(4) 0.1492(3) 0.0660(8) Uani 1 1 d . . .
H8 H 0.9953 0.1731 0.1221 0.079 Uiso 1 1 calc R . .
C9 C 0.9963(5) 0.3898(4) 0.2666(3) 0.0637(8) Uani 1 1 d . . .
H9 H 1.1218 0.4175 0.3288 0.076 Uiso 1 1 calc R . .
C10 C 0.6938(5) 0.1104(4) 0.4158(4) 0.0712(9) Uani 1 1 d . . .
H10A H 0.6271 -0.0035 0.3732 0.107 Uiso 1 1 calc R . .
H10B H 0.7080 0.1553 0.5180 0.107 Uiso 1 1 calc R . .
H10C H 0.8288 0.1289 0.3932 0.107 Uiso 1 1 calc R . .
C11 C 0.3543(5) 0.1739(4) 0.3966(4) 0.0752(9) Uani 1 1 d . . .
H11A H 0.2806 0.2300 0.3607 0.113 Uiso 1 1 calc R . .
H11B H 0.3706 0.2200 0.4989 0.113 Uiso 1 1 calc R . .
H11C H 0.2771 0.0620 0.3544 0.113 Uiso 1 1 calc R . .
C12 C 0.8502(5) 0.6734(4) 0.1587(4) 0.0660(8) Uani 1 1 d . . .
C13 C 0.6794(4) 0.3664(4) -0.1015(3) 0.0602(8) Uani 1 1 d . . .
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'
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
C2 O1 C1 108.89(19) . . ?
C7 O2 C1 110.0(2) . . ?
O2 C1 O1 104.8(2) . . ?
O2 C1 C10 108.8(3) . . ?
O1 C1 C10 108.5(2) . . ?
O2 C1 C11 110.9(2) . . ?
O1 C1 C11 110.5(3) . . ?
C10 C1 C11 112.9(2) . . ?
O1 C2 C7 104.8(2) . . ?
O1 C2 C3 109.5(2) . . ?
C7 C2 C3 109.2(2) . . ?
O1 C2 H2 111.1 . . ?
C7 C2 H2 111.1 . . ?
C3 C2 H2 111.1 . . ?
C9 C3 C4 108.4(2) . . ?
C9 C3 C2 106.5(2) . . ?
C4 C3 C2 104.7(2) . . ?
C9 C3 H3 112.2 . . ?
C4 C3 H3 112.2 . . ?
C2 C3 H3 112.2 . . ?
C5 C4 C12 123.3(3) . . ?
C5 C4 C3 113.5(2) . . ?
C12 C4 C3 123.2(2) . . ?
C4 C5 C13 124.3(3) . . ?
C4 C5 C6 113.7(2) . . ?
C13 C5 C6 122.0(2) . . ?
C8 C6 C5 107.9(2) . . ?
C8 C6 C7 106.3(2) . . ?
C5 C6 C7 104.1(2) . . ?
C8 C6 H6 112.7 . . ?
C5 C6 H6 112.7 . . ?
C7 C6 H6 112.7 . . ?
O2 C7 C2 105.3(2) . . ?
O2 C7 C6 109.8(2) . . ?
C2 C7 C6 109.2(2) . . ?
O2 C7 H7 110.8 . . ?
C2 C7 H7 110.8 . . ?
C6 C7 H7 110.8 . . ?
C9 C8 C6 114.4(3) . . ?
C9 C8 H8 122.8 . . ?
C6 C8 H8 122.8 . . ?
C8 C9 C3 114.3(3) . . ?
C8 C9 H9 122.9 . . ?
C3 C9 H9 122.9 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C4 178.4(3) . . ?
N1 C13 C5 178.7(4) . . ?
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
O1 C2 1.426(3) . ?
O1 C1 1.436(3) . ?
O2 C7 1.409(3) . ?
O2 C1 1.422(3) . ?
N1 C13 1.138(3) . ?
N2 C12 1.140(4) . ?
C1 C10 1.496(5) . ?
C1 C11 1.503(4) . ?
C2 C7 1.529(4) . ?
C2 C3 1.553(4) . ?
C2 H2 0.9800 . ?
C3 C9 1.487(4) . ?
C3 C4 1.510(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.342(4) . ?
C4 C12 1.432(4) . ?
C5 C13 1.424(4) . ?
C5 C6 1.512(4) . ?
C6 C8 1.508(4) . ?
C6 C7 1.555(4) . ?
C6 H6 0.9800 . ?
C7 H7 0.9800 . ?
C8 C9 1.318(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O2 C1 O1 -23.9(3) . . . . ?
C7 O2 C1 C10 -139.8(2) . . . . ?
C7 O2 C1 C11 95.4(3) . . . . ?
C2 O1 C1 O2 24.9(3) . . . . ?
C2 O1 C1 C10 141.0(2) . . . . ?
C2 O1 C1 C11 -94.7(3) . . . . ?
C1 O1 C2 C7 -16.4(3) . . . . ?
C1 O1 C2 C3 -133.4(2) . . . . ?
O1 C2 C3 C9 56.9(3) . . . . ?
C7 C2 C3 C9 -57.2(3) . . . . ?
O1 C2 C3 C4 171.7(2) . . . . ?
C7 C2 C3 C4 57.5(3) . . . . ?
C9 C3 C4 C5 52.4(3) . . . . ?
C2 C3 C4 C5 -61.1(3) . . . . ?
C9 C3 C4 C12 -125.5(3) . . . . ?
C2 C3 C4 C12 121.0(3) . . . . ?
C12 C4 C5 C13 -3.8(4) . . . . ?
C3 C4 C5 C13 178.3(2) . . . . ?
C12 C4 C5 C6 178.0(2) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C8 -51.4(3) . . . . ?
C13 C5 C6 C8 130.2(3) . . . . ?
C4 C5 C6 C7 61.2(3) . . . . ?
C13 C5 C6 C7 -117.2(3) . . . . ?
C1 O2 C7 C2 13.8(3) . . . . ?
C1 O2 C7 C6 131.3(2) . . . . ?
O1 C2 C7 O2 1.8(3) . . . . ?
C3 C2 C7 O2 118.9(2) . . . . ?
O1 C2 C7 C6 -116.1(2) . . . . ?
C3 C2 C7 C6 1.0(3) . . . . ?
C8 C6 C7 O2 -60.0(3) . . . . ?
C5 C6 C7 O2 -173.85(19) . . . . ?
C8 C6 C7 C2 55.0(3) . . . . ?
C5 C6 C7 C2 -58.8(3) . . . . ?
C5 C6 C8 C9 51.7(3) . . . . ?
C7 C6 C8 C9 -59.5(3) . . . . ?
C6 C8 C9 C3 0.6(4) . . . . ?
C4 C3 C9 C8 -53.0(3) . . . . ?
C2 C3 C9 C8 59.2(3) . . . . ?
