#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:30:04 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301811 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/20/4002005.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_4002005
loop_
_publ_author_name
'Doi, Iori'
'Miyazaki, Eigo'
'Takimiya, Kazuo'
'Kunugi, Yoshihito'
_publ_section_title
;
 Development ofN-Alkyl-Substituted Bis(pyrrolo[3,4-d])tetrathiafulvalenes
 as Organic Semiconductors for Solution-Processible Field-Effect
 Transistors
;
_journal_issue                   22
_journal_name_full               'Chemistry of Materials'
_journal_page_first              5230
_journal_paper_doi               10.1021/cm070956+
_journal_volume                  19
_journal_year                    2007
_chemical_formula_sum            'C42 H70 N2 S4'
_chemical_formula_weight         731.27
_chemical_melting_point          393.7(5)
_chemical_name_common            Bis(N-n-cetylpyrrolo[3,4-d])TTF
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.34(2)
_cell_angle_beta                 94.06(2)
_cell_angle_gamma                103.68(2)
_cell_formula_units_Z            1
_cell_length_a                   5.394(3)
_cell_length_b                   7.502(3)
_cell_length_c                   26.920(2)
_cell_measurement_reflns_used    7684
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.5
_cell_volume                     1053.9(7)
_computing_cell_refinement       PROCESS-AUTO'
_computing_data_collection       PROCESS-AUTO'
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.819
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            7780
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0564
_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)+(0.1290P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1777
_reflns_number_gt                2751
_reflns_number_total             3934
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm070956%2B%2B-file003.cif
_cod_data_source_block           6(R=n-cetyl)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '393.2-394.2' was changed to
'393.7(5)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1053.8(9)
_cod_database_code               4002005
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
S1 S 0.28083(14) 0.57442(9) 0.56518(3) 0.0363(2) Uani 1 1 d
S2 S 0.10003(14) 0.23137(9) 0.49728(2) 0.0337(2) Uani 1 1 d
N1 N 0.6552(5) 0.1938(3) 0.59746(8) 0.0350(6) Uani 1 1 d
C1 C 0.0812(5) 0.4598(3) 0.51286(9) 0.0290(6) Uani 1 1 d
C2 C 0.4337(5) 0.3960(4) 0.57488(9) 0.0309(6) Uani 1 1 d
C3 C 0.6260(6) 0.3698(4) 0.60813(10) 0.0343(6) Uani 1 1 d
C4 C 0.4889(6) 0.1117(4) 0.55820(10) 0.0329(6) Uani 1 1 d
C5 C 0.3479(5) 0.2343(3) 0.54325(9) 0.0301(6) Uani 1 1 d
C6 C 0.8589(6) 0.1168(4) 0.62035(10) 0.0365(7) Uani 1 1 d
C7 C 0.7739(6) -0.0251(4) 0.65825(10) 0.0352(6) Uani 1 1 d
C8 C 0.9896(6) -0.1180(4) 0.67215(10) 0.0379(7) Uani 1 1 d
C9 C 0.9294(6) -0.2639(4) 0.71065(10) 0.0370(7) Uani 1 1 d
C10 C 1.1375(6) -0.3696(4) 0.71817(10) 0.0376(7) Uani 1 1 d
C11 C 1.0734(6) -0.5264(4) 0.75302(10) 0.0401(7) Uani 1 1 d
C12 C 1.2836(6) -0.6295(4) 0.76077(10) 0.0395(7) Uani 1 1 d
C13 C 1.2204(6) -0.7859(4) 0.79590(11) 0.0406(7) Uani 1 1 d
C14 C 1.4313(6) -0.8880(4) 0.80446(11) 0.0399(7) Uani 1 1 d
C15 C 1.3690(6) -1.0416(4) 0.84039(11) 0.0414(7) Uani 1 1 d
C16 C 1.5794(6) -1.1435(4) 0.84908(11) 0.0427(7) Uani 1 1 d
C17 C 1.5183(6) -1.2977(4) 0.88497(11) 0.0416(7) Uani 1 1 d
C18 C 1.7320(6) -1.3980(4) 0.89332(11) 0.0425(7) Uani 1 1 d
C19 C 1.6724(7) -1.5524(4) 0.92898(11) 0.0458(8) Uani 1 1 d
C20 C 1.8825(7) -1.6558(5) 0.93578(12) 0.0552(9) Uani 1 1 d
C21 C 1.8248(10) -1.8115(6) 0.97097(15) 0.0776(13) Uani 1 1 d
H1 H 0.7182 0.4560 0.6342 0.037 Uiso 1 1 d
H2 H 0.4716 -0.0102 0.5437 0.039 Uiso 1 1 d
H3 H 0.9320 0.0598 0.5945 0.043 Uiso 1 1 d
H4 H 0.9895 0.2147 0.6366 0.043 Uiso 1 1 d
H5 H 0.7281 0.0334 0.6872 0.041 Uiso 1 1 d
H6 H 0.6253 -0.1151 0.6441 0.041 Uiso 1 1 d
H7 H 1.0309 -0.1742 0.6424 0.045 Uiso 1 1 d
H8 H 1.1352 -0.0246 0.6852 0.045 Uiso 1 1 d
H9 H 0.9088 -0.2056 0.7417 0.045 Uiso 1 1 d
H10 H 0.7708 -0.3493 0.6995 0.045 Uiso 1 1 d
H11 H 1.1675 -0.4191 0.6865 0.046 Uiso 1 1 d
H12 H 1.2924 -0.2855 0.7318 0.046 Uiso 1 1 d
H13 H 1.0433 -0.4775 0.7847 0.047 Uiso 1 1 d
H14 H 0.9201 -0.6114 0.7394 0.047 Uiso 1 1 d
H15 H 1.3119 -0.6819 0.7292 0.048 Uiso 1 1 d
H16 H 1.4376 -0.5460 0.7739 0.048 Uiso 1 1 d
H17 H 1.1911 -0.7339 0.8272 0.049 Uiso 1 1 d
H18 H 1.0694 -0.8704 0.7824 0.049 Uiso 1 1 d
H19 H 1.4599 -0.9407 0.7733 0.048 Uiso 1 1 d
H20 H 1.5845 -0.8020 0.8175 0.048 Uiso 1 1 d
H21 H 1.3398 -0.9872 0.8718 0.049 Uiso 1 1 d
H22 H 1.2148 -1.1258 0.8276 0.049 Uiso 1 1 d
H23 H 1.6100 -1.1950 0.8178 0.052 Uiso 1 1 d
H24 H 1.7325 -1.0583 0.8625 0.052 Uiso 1 1 d
H25 H 1.4826 -1.2484 0.9159 0.050 Uiso 1 1 d
H26 H 1.3658 -1.3861 0.8710 0.050 Uiso 1 1 d
H27 H 1.7655 -1.4493 0.8624 0.052 Uiso 1 1 d
H28 H 1.8838 -1.3105 0.9070 0.052 Uiso 1 1 d
H29 H 1.6486 -1.4991 0.9608 0.054 Uiso 1 1 d
H30 H 1.5176 -1.6356 0.9166 0.054 Uiso 1 1 d
H31 H 1.9111 -1.7057 0.9039 0.067 Uiso 1 1 d
H32 H 2.0408 -1.5702 0.9485 0.067 Uiso 1 1 d
H33 H 1.8067 -1.7612 1.0030 0.091 Uiso 1 1 d
H34 H 1.6756 -1.8965 0.9585 0.091 Uiso 1 1 d
H35 H 1.9660 -1.8691 0.9732 0.091 Uiso 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'
S S 0.1246 0.1234 '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'
H H 0.0000 0.0000 '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_publ_flag
C2 S1 C1 94.51(12) . yes
C5 S2 C1 94.40(12) . yes
C4 N1 C3 110.0(2) . yes
C4 N1 C6 124.5(2) . yes
C3 N1 C6 124.9(2) . yes
C1 C1 S1 121.5(3) 2_566 yes
C1 C1 S2 121.9(3) 2_566 yes
S1 C1 S2 116.55(14) . yes
C3 C2 C5 107.9(2) . yes
C3 C2 S1 134.9(2) . yes
C5 C2 S1 117.3(2) . yes
C2 C3 N1 106.9(2) . yes
C2 C3 H1 126.2(3) . yes
N1 C3 H1 126.9(3) . yes
N1 C4 C5 107.8(2) . yes
N1 C4 H2 126.1(3) . yes
C5 C4 H2 126.1(3) . yes
C4 C5 C2 107.4(2) . yes
C4 C5 S2 135.5(2) . yes
C2 C5 S2 117.1(2) . yes
N1 C6 C7 115.1(2) . yes
N1 C6 H3 108.5(2) . yes
C7 C6 H3 107.9(2) . yes
N1 C6 H4 108.9(2) . yes
C7 C6 H4 108.0(2) . yes
H3 C6 H4 108.4(3) . yes
C6 C7 C8 109.7(2) . yes
C6 C7 H5 109.5(2) . yes
C8 C7 H5 110.3(2) . yes
C6 C7 H6 109.2(2) . yes
C8 C7 H6 110.0(2) . yes
H5 C7 H6 108.2(3) . yes
C7 C8 C9 115.1(2) . yes
C7 C8 H7 108.0(2) . yes
C9 C8 H7 108.6(2) . yes
C7 C8 H8 107.8(2) . yes
C9 C8 H8 108.5(2) . yes
H7 C8 H8 108.7(3) . yes
C10 C9 C8 112.8(2) . yes
C10 C9 H9 109.3(2) . yes
C8 C9 H9 108.9(2) . yes
C10 C9 H10 108.8(3) . yes
C8 C9 H10 108.6(2) . yes
H9 C9 H10 108.4(3) . yes
C11 C10 C9 114.1(2) . yes
C11 C10 H11 108.5(3) . yes
C9 C10 H11 109.0(2) . yes
C11 C10 H12 108.2(2) . yes
C9 C10 H12 108.6(2) . yes
H11 C10 H12 108.3(3) . yes
C12 C11 C10 113.7(3) . yes
C12 C11 H13 108.5(3) . yes
C10 C11 H13 108.7(3) . yes
C12 C11 H14 108.7(3) . yes
C10 C11 H14 108.5(2) . yes
H13 C11 H14 108.7(3) . yes
C11 C12 C13 113.8(3) . yes
C11 C12 H15 109.0(3) . yes
C13 C12 H15 107.5(3) . yes
C11 C12 H16 109.4(3) . yes
C13 C12 H16 108.3(3) . yes
H15 C12 H16 108.8(3) . yes
C14 C13 C12 114.1(3) . yes
C14 C13 H17 108.5(3) . yes
C12 C13 H17 107.4(3) . yes
C14 C13 H18 108.8(3) . yes
C12 C13 H18 108.3(3) . yes
H17 C13 H18 109.6(3) . yes
C13 C14 C15 113.9(3) . yes
C13 C14 H19 108.6(3) . yes
C15 C14 H19 108.1(3) . yes
C13 C14 H20 108.7(3) . yes
C15 C14 H20 108.5(3) . yes
H19 C14 H20 109.1(3) . yes
C16 C15 C14 114.0(3) . yes
C16 C15 H21 108.9(3) . yes
C14 C15 H21 107.6(3) . yes
C16 C15 H22 109.6(3) . yes
C14 C15 H22 108.3(3) . yes
H21 C15 H22 108.3(3) . yes
C15 C16 C17 114.3(3) . yes
C15 C16 H23 108.5(3) . yes
C17 C16 H23 108.5(3) . yes
C15 C16 H24 109.0(3) . yes
C17 C16 H24 107.7(3) . yes
H23 C16 H24 108.7(3) . yes
C16 C17 C18 113.5(3) . yes
C16 C17 H25 109.1(3) . yes
C18 C17 H25 109.8(3) . yes
C16 C17 H26 107.9(3) . yes
C18 C17 H26 108.2(3) . yes
H25 C17 H26 108.2(3) . yes
C19 C18 C17 113.9(3) . yes
C19 C18 H27 107.9(3) . yes
C17 C18 H27 109.8(3) . yes
C19 C18 H28 108.0(3) . yes
C17 C18 H28 108.4(3) . yes
H27 C18 H28 108.7(3) . yes
C20 C19 C18 113.6(3) . yes
C20 C19 H29 108.9(3) . yes
C18 C19 H29 107.8(3) . yes
C20 C19 H30 109.3(3) . yes
C18 C19 H30 108.3(3) . yes
H29 C19 H30 108.8(3) . yes
C21 C20 C19 114.2(3) . yes
C21 C20 H31 108.5(3) . yes
C19 C20 H31 109.2(3) . yes
C21 C20 H32 108.4(3) . yes
C19 C20 H32 109.2(3) . yes
H31 C20 H32 107.1(4) . yes
C20 C21 H33 108.6(4) . yes
C20 C21 H34 109.0(3) . yes
H33 C21 H34 111.2(5) . yes
C20 C21 H35 109.0(4) . yes
H33 C21 H35 108.9(4) . yes
H34 C21 H35 110.1(4) . yes
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
S1 C2 1.749(3) . yes
S1 C1 1.769(3) . yes
S2 C5 1.752(3) . yes
S2 C1 1.775(3) . yes
N1 C4 1.361(4) . yes
N1 C3 1.387(4) . yes
N1 C6 1.467(3) . yes
C1 C1 1.345(5) 2_566 yes
C2 C3 1.377(4) . yes
C2 C5 1.416(4) . yes
C3 H1 0.959(3) . yes
C4 C5 1.380(4) . yes
C4 H2 0.961(3) . yes
C6 C7 1.520(4) . yes
C6 H3 0.958(3) . yes
C6 H4 0.955(3) . yes
C7 C8 1.524(4) . yes
C7 H5 0.955(3) . yes
C7 H6 0.961(3) . yes
C8 C9 1.533(4) . yes
C8 H7 0.954(3) . yes
C8 H8 0.955(3) . yes
C9 C10 1.527(4) . yes
C9 H9 0.954(3) . yes
C9 H10 0.959(3) . yes
C10 C11 1.526(4) . yes
C10 H11 0.955(3) . yes
C10 H12 0.958(3) . yes
C11 C12 1.524(4) . yes
C11 H13 0.953(3) . yes
C11 H14 0.956(3) . yes
C12 C13 1.528(4) . yes
C12 H15 0.958(3) . yes
C12 H16 0.950(3) . yes
C13 C14 1.525(4) . yes
C13 H17 0.953(3) . yes
C13 H18 0.945(3) . yes
C14 C15 1.526(4) . yes
C14 H19 0.950(3) . yes
C14 H20 0.954(3) . yes
C15 C16 1.522(4) . yes
C15 H21 0.964(3) . yes
C15 H22 0.950(3) . yes
C16 C17 1.528(4) . yes
C16 H23 0.954(3) . yes
C16 H24 0.955(3) . yes
C17 C18 1.527(4) . yes
C17 H25 0.947(3) . yes
C17 H26 0.967(3) . yes
C18 C19 1.525(4) . yes
C18 H27 0.949(3) . yes
C18 H28 0.959(3) . yes
C19 C20 1.522(4) . yes
C19 H29 0.961(3) . yes
C19 H30 0.946(4) . yes
C20 C21 1.522(5) . yes
C20 H31 0.959(4) . yes
C20 H32 0.970(4) . yes
C21 H33 0.947(4) . yes
C21 H34 0.933(5) . yes
C21 H35 0.960(5) . yes
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_4
_geom_torsion_publ_flag
C2 S1 C1 C1 -177.3(3) 2_566 yes
C2 S1 C1 S2 4.46(17) . yes
C5 S2 C1 C1 177.6(3) 2_566 yes
C5 S2 C1 S1 -4.15(17) . yes
C1 S1 C2 C3 178.3(3) . yes
C1 S1 C2 C5 -3.1(2) . yes
C5 C2 C3 N1 -0.8(3) . yes
S1 C2 C3 N1 177.9(2) . yes
C4 N1 C3 C2 0.8(3) . yes
C6 N1 C3 C2 172.9(2) . yes
C3 N1 C4 C5 -0.5(3) . yes
C6 N1 C4 C5 -172.6(2) . yes
N1 C4 C5 C2 0.0(3) . yes
N1 C4 C5 S2 -179.0(2) . yes
C3 C2 C5 C4 0.5(3) . yes
S1 C2 C5 C4 -178.50(19) . yes
C3 C2 C5 S2 179.69(19) . yes
S1 C2 C5 S2 0.7(3) . yes
C1 S2 C5 C4 -179.0(3) . yes
C1 S2 C5 C2 2.0(2) . yes
C4 N1 C6 C7 -82.4(3) . yes
C3 N1 C6 C7 106.6(3) . yes
N1 C6 C7 C8 170.0(2) . yes
C6 C7 C8 C9 179.5(2) . yes
C7 C8 C9 C10 172.6(2) . yes
C8 C9 C10 C11 -175.2(2) . yes
C9 C10 C11 C12 -179.3(2) . yes
C10 C11 C12 C13 179.7(2) . yes
C11 C12 C13 C14 -179.2(3) . yes
C12 C13 C14 C15 178.9(2) . yes
C13 C14 C15 C16 -179.9(3) . yes
C14 C15 C16 C17 -179.9(3) . yes
C15 C16 C17 C18 -179.8(3) . yes
C16 C17 C18 C19 -179.8(3) . yes
C17 C18 C19 C20 178.1(3) . yes
C18 C19 C20 C21 -179.6(3) . yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101441911
