#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/38/1513827.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_1513827
loop_
_publ_author_name
'Mori, Takamichi'
'Yanai, Naoyuki'
'Osaka, Itaru'
'Takimiya, Kazuo'
_publ_section_title
;
 Quinoidal Naphtho[1,2-b:5,6-b']dithiophenes for Solution-Processed
 n-Channel Organic Field-Effect Transistors.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1334
_journal_page_last               1337
_journal_paper_doi               10.1021/ol5000567
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C44 H54 N4 S2'
_chemical_formula_sum            'C44 H54 N4 S2'
_chemical_formula_weight         703.03
_chemical_name_common            C12-QNDT-CN
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.0404(15)
_cell_angle_beta                 95.4568(14)
_cell_angle_gamma                99.291(2)
_cell_formula_units_Z            1
_cell_length_a                   4.62000(10)
_cell_length_b                   14.0234(3)
_cell_length_c                   15.5359(4)
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      3.81
_cell_volume                     973.48(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      99(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_sigmaI/netI    0.1108
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10337
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         3.24
_exptl_absorpt_coefficient_mu    1.502
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.5849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             378
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0692
_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)+(0.1076P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.2009
_reflns_number_gt                2151
_reflns_number_total             3484
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5000567_si_002.cif
_cod_data_source_block           C12-QNDT-CN
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1513827
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
S1 S 0.72952(19) 0.33891(5) 0.12293(6) 0.0321(3) Uani 1 1 d .
C1 C 0.5921(7) 0.4865(2) 0.0343(2) 0.0296(8) Uani 1 1 d .
C26 C 0.8156(9) 0.1532(2) 0.1870(3) 0.0364(9) Uani 1 1 d .
C27 C 0.1788(7) 0.4408(2) -0.0879(2) 0.0313(8) Uani 1 1 d .
H26 H 0.0604 0.4604 -0.1330 0.038 Uiso 1 1 calc R
C5 C 0.5155(7) 0.2236(2) 0.0844(2) 0.0287(8) Uani 1 1 d .
C6 C 0.0031(7) 0.2025(2) -0.2050(2) 0.0317(8) Uani 1 1 d .
H1 H 0.1166 0.2422 -0.2420 0.038 Uiso 1 1 calc R
H2 H 0.1399 0.1668 -0.1755 0.038 Uiso 1 1 calc R
C7 C -0.2585(8) -0.1056(2) -0.4389(2) 0.0325(8) Uani 1 1 d .
H3 H -0.1064 -0.1324 -0.4055 0.039 Uiso 1 1 calc R
H4 H -0.1621 -0.0728 -0.4834 0.039 Uiso 1 1 calc R
C8 C 0.3073(7) 0.3172(2) -0.0087(2) 0.0291(8) Uani 1 1 d .
C9 C -0.3843(8) -0.2652(2) -0.5490(2) 0.0349(9) Uani 1 1 d .
H5 H -0.2245 -0.2896 -0.5167 0.042 Uiso 1 1 calc R
H6 H -0.2979 -0.2324 -0.5950 0.042 Uiso 1 1 calc R
C10 C 0.5354(7) 0.3891(2) 0.0455(2) 0.0277(8) Uani 1 1 d .
C11 C 0.1234(7) 0.3459(2) -0.0772(2) 0.0289(8) Uani 1 1 d .
C12 C 0.2965(8) 0.2251(2) 0.0152(2) 0.0323(8) Uani 1 1 d .
H27 H 0.1557 0.1689 -0.0124 0.039 Uiso 1 1 calc R
C13 C -0.1294(8) 0.0512(2) -0.3252(2) 0.0319(8) Uani 1 1 d .
H7 H -0.0196 0.0837 -0.3675 0.038 Uiso 1 1 calc R
H8 H 0.0109 0.0212 -0.2906 0.038 Uiso 1 1 calc R
C14 C -0.1148(8) 0.2708(2) -0.1355(2) 0.0321(8) Uani 1 1 d .
H9 H -0.2541 0.3054 -0.1653 0.039 Uiso 1 1 calc R
H10 H -0.2266 0.2307 -0.0984 0.039 Uiso 1 1 calc R
C15 C -0.3726(7) -0.0297(2) -0.3761(2) 0.0328(8) Uani 1 1 d .
H11 H -0.5150 0.0003 -0.4100 0.039 Uiso 1 1 calc R
H12 H -0.4801 -0.0632 -0.3339 0.039 Uiso 1 1 calc R
C16 C 0.5693(8) 0.1430(2) 0.1211(2) 0.0329(8) Uani 1 1 d .
C17 C -0.2424(7) 0.1285(2) -0.2634(2) 0.0319(8) Uani 1 1 d .
H13 H -0.3635 0.1641 -0.2987 0.038 Uiso 1 1 calc R
H14 H -0.3720 0.0952 -0.2258 0.038 Uiso 1 1 calc R
C18 C -0.6214(8) -0.3526(2) -0.5931(2) 0.0369(9) Uani 1 1 d .
H15 H -0.7821 -0.3281 -0.6249 0.044 Uiso 1 1 calc R
H16 H -0.7066 -0.3857 -0.5471 0.044 Uiso 1 1 calc R
N2 N 1.0205(8) 0.1660(2) 0.2381(2) 0.0459(9) Uani 1 1 d .
N1 N 0.2410(7) -0.0274(2) 0.0729(2) 0.0469(9) Uani 1 1 d .
C21 C 0.3863(8) 0.0480(2) 0.0939(2) 0.0359(9) Uani 1 1 d .
C22 C -0.4980(8) -0.1904(2) -0.4859(2) 0.0358(9) Uani 1 1 d .
H17 H -0.5929 -0.2237 -0.4415 0.043 Uiso 1 1 calc R
H18 H -0.6512 -0.1636 -0.5188 0.043 Uiso 1 1 calc R
C23 C -0.7332(9) -0.5193(3) -0.6953(3) 0.0447(10) Uani 1 1 d .
H19 H -0.6564 -0.5567 -0.7449 0.054 Uiso 1 1 calc R
H20 H -0.9168 -0.4996 -0.7189 0.054 Uiso 1 1 calc R
C24 C -0.5086(8) -0.4281(2) -0.6576(3) 0.0413(10) Uani 1 1 d .
H21 H -0.4410 -0.3965 -0.7066 0.050 Uiso 1 1 calc R
H22 H -0.3351 -0.4477 -0.6272 0.050 Uiso 1 1 calc R
C25 C -0.8073(11) -0.5857(3) -0.6299(3) 0.0638(13) Uani 1 1 d .
H23 H -0.6291 -0.6088 -0.6086 0.096 Uiso 1 1 calc R
H24 H -0.9582 -0.6421 -0.6583 0.096 Uiso 1 1 calc R
H25 H -0.8829 -0.5494 -0.5803 0.096 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 0.0181 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'
S S 0.3331 0.5567 '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
C10 S1 C5 91.06(15) . .
C10 C1 C1 116.9(4) . 2_665
C10 C1 C27 123.1(3) . 2_665
C1 C1 C27 119.9(4) 2_665 2_665
N2 C26 C16 176.2(4) . .
C11 C27 C1 123.3(3) . 2_665
C11 C27 H26 118.4 . .
C1 C27 H26 118.4 2_665 .
C16 C5 C12 127.2(3) . .
C16 C5 S1 120.7(3) . .
C12 C5 S1 112.1(2) . .
C17 C6 C14 112.5(3) . .
C17 C6 H1 109.1 . .
C14 C6 H1 109.1 . .
C17 C6 H2 109.1 . .
C14 C6 H2 109.1 . .
H1 C6 H2 107.8 . .
C15 C7 C22 113.8(3) . .
C15 C7 H3 108.8 . .
C22 C7 H3 108.8 . .
C15 C7 H4 108.8 . .
C22 C7 H4 108.8 . .
H3 C7 H4 107.7 . .
C12 C8 C10 111.6(3) . .
C12 C8 C11 128.8(3) . .
C10 C8 C11 119.6(3) . .
C22 C9 C18 113.8(3) . .
C22 C9 H5 108.8 . .
C18 C9 H5 108.8 . .
C22 C9 H6 108.8 . .
C18 C9 H6 108.8 . .
H5 C9 H6 107.7 . .
C1 C10 C8 122.6(3) . .
C1 C10 S1 125.4(3) . .
C8 C10 S1 111.9(2) . .
C27 C11 C8 117.6(3) . .
C27 C11 C14 122.2(3) . .
C8 C11 C14 120.2(3) . .
C8 C12 C5 113.2(3) . .
C8 C12 H27 123.4 . .
C5 C12 H27 123.4 . .
C15 C13 C17 113.7(3) . .
C15 C13 H7 108.8 . .
C17 C13 H7 108.8 . .
C15 C13 H8 108.8 . .
C17 C13 H8 108.8 . .
H7 C13 H8 107.7 . .
C11 C14 C6 113.7(3) . .
C11 C14 H9 108.8 . .
C6 C14 H9 108.8 . .
C11 C14 H10 108.8 . .
C6 C14 H10 108.8 . .
H9 C14 H10 107.7 . .
C13 C15 C7 113.4(3) . .
C13 C15 H11 108.9 . .
C7 C15 H11 108.9 . .
C13 C15 H12 108.9 . .
C7 C15 H12 108.9 . .
H11 C15 H12 107.7 . .
C5 C16 C26 119.8(3) . .
C5 C16 C21 121.9(3) . .
C26 C16 C21 118.3(3) . .
C6 C17 C13 113.5(3) . .
C6 C17 H13 108.9 . .
C13 C17 H13 108.9 . .
C6 C17 H14 108.9 . .
C13 C17 H14 108.9 . .
H13 C17 H14 107.7 . .
C9 C18 C24 114.1(3) . .
C9 C18 H15 108.7 . .
C24 C18 H15 108.7 . .
C9 C18 H16 108.7 . .
C24 C18 H16 108.7 . .
H15 C18 H16 107.6 . .
N1 C21 C16 179.5(4) . .
C9 C22 C7 113.6(3) . .
C9 C22 H17 108.8 . .
C7 C22 H17 108.8 . .
C9 C22 H18 108.8 . .
C7 C22 H18 108.8 . .
H17 C22 H18 107.7 . .
C24 C23 C25 114.0(3) . .
C24 C23 H19 108.8 . .
C25 C23 H19 108.8 . .
C24 C23 H20 108.8 . .
C25 C23 H20 108.8 . .
H19 C23 H20 107.6 . .
C23 C24 C18 114.6(3) . .
C23 C24 H21 108.6 . .
C18 C24 H21 108.6 . .
C23 C24 H22 108.6 . .
C18 C24 H22 108.6 . .
H21 C24 H22 107.6 . .
C23 C25 H23 109.5 . .
C23 C25 H24 109.5 . .
H23 C25 H24 109.5 . .
C23 C25 H25 109.5 . .
H23 C25 H25 109.5 . .
H24 C25 H25 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C10 1.736(3) .
S1 C5 1.737(3) .
C1 C10 1.390(4) .
C1 C1 1.435(7) 2_665
C1 C27 1.439(4) 2_665
C26 N2 1.147(5) .
C26 C16 1.429(5) .
C27 C11 1.354(4) .
C27 C1 1.439(4) 2_665
C27 H26 0.9500 .
C5 C16 1.390(4) .
C5 C12 1.409(5) .
C6 C17 1.521(4) .
C6 C14 1.529(4) .
C6 H1 0.9900 .
C6 H2 0.9900 .
C7 C15 1.522(4) .
C7 C22 1.523(4) .
C7 H3 0.9900 .
C7 H4 0.9900 .
C8 C12 1.393(4) .
C8 C10 1.435(4) .
C8 C11 1.446(5) .
C9 C22 1.513(5) .
C9 C18 1.527(5) .
C9 H5 0.9900 .
C9 H6 0.9900 .
C11 C14 1.509(5) .
C12 H27 0.9500 .
C13 C15 1.520(4) .
C13 C17 1.524(4) .
C13 H7 0.9900 .
C13 H8 0.9900 .
C14 H9 0.9900 .
C14 H10 0.9900 .
C15 H11 0.9900 .
C15 H12 0.9900 .
C16 C21 1.434(5) .
C17 H13 0.9900 .
C17 H14 0.9900 .
C18 C24 1.530(4) .
C18 H15 0.9900 .
C18 H16 0.9900 .
N1 C21 1.139(4) .
C22 H17 0.9900 .
C22 H18 0.9900 .
C23 C24 1.509(5) .
C23 C25 1.509(5) .
C23 H19 0.9900 .
C23 H20 0.9900 .
C24 H21 0.9900 .
C24 H22 0.9900 .
C25 H23 0.9800 .
C25 H24 0.9800 .
C25 H25 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
C10 S1 C5 C16 178.4(3) .
C10 S1 C5 C12 -1.4(3) .
C1 C1 C10 C8 0.8(5) 2_665
C27 C1 C10 C8 -179.7(3) 2_665
C1 C1 C10 S1 179.4(3) 2_665
C27 C1 C10 S1 -1.1(5) 2_665
C12 C8 C10 C1 179.4(3) .
C11 C8 C10 C1 -1.0(5) .
C12 C8 C10 S1 0.7(3) .
C11 C8 C10 S1 -179.8(2) .
C5 S1 C10 C1 -178.3(3) .
C5 S1 C10 C8 0.4(2) .
C1 C27 C11 C8 -0.5(5) 2_665
C1 C27 C11 C14 -178.9(3) 2_665
C12 C8 C11 C27 -179.8(3) .
C10 C8 C11 C27 0.8(4) .
C12 C8 C11 C14 -1.4(5) .
C10 C8 C11 C14 179.2(3) .
C10 C8 C12 C5 -1.8(4) .
C11 C8 C12 C5 178.7(3) .
C16 C5 C12 C8 -177.7(3) .
S1 C5 C12 C8 2.1(4) .
C27 C11 C14 C6 102.8(4) .
C8 C11 C14 C6 -75.5(4) .
C17 C6 C14 C11 -179.3(3) .
C17 C13 C15 C7 179.0(3) .
C22 C7 C15 C13 176.4(3) .
C12 C5 C16 C26 175.4(3) .
S1 C5 C16 C26 -4.4(5) .
C12 C5 C16 C21 -3.6(6) .
S1 C5 C16 C21 176.5(3) .
N2 C26 C16 C5 -23(6) .
N2 C26 C16 C21 156(6) .
C14 C6 C17 C13 -172.4(3) .
C15 C13 C17 C6 173.3(3) .
C22 C9 C18 C24 179.5(3) .
C5 C16 C21 N1 -134(48) .
C26 C16 C21 N1 47(48) .
C18 C9 C22 C7 177.3(3) .
C15 C7 C22 C9 179.4(3) .
C25 C23 C24 C18 -70.4(4) .
C9 C18 C24 C23 174.6(3) .
