#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:45:17 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180275 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/61/7116144.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_7116144
loop_
_publ_author_name
'Joydeep Dhar'
'Durga Prasad Karothu'
'Satish Patil'
_publ_section_title
;
 Herringbone to cofacial solid state packing via H-bonding in
 diketopyrrolopyrrole (DPP) based molecular crystals: influence on charge
 transport
;
_journal_name_full               Chem.Commun.
_journal_page_first              51
_journal_paper_doi               10.1039/C4cc06063F
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C20 H20 N2 O2 S2'
_chemical_formula_weight         384.50
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 95.528(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   5.215(5)
_cell_length_b                   23.832(5)
_cell_length_c                   14.377(5)
_cell_measurement_temperature    120(2)
_cell_volume                     1778.5(19)
_computing_cell_refinement       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97  (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0635
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13705
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.317
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.229
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0689
_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)+(0.0113P)²+6.2389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1495
_reflns_number_gt                2495
_reflns_number_total             3124
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc06063f2.cif
_cod_data_source_block           dpj-new-r
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7116144
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S -0.7478(2) 0.25143(5) -0.25110(8) 0.0209(3) Uani 1 1 d . . .
S1A S 0.3051(3) 0.13492(6) 0.16532(10) 0.0182(6) Uani 0.701(16) 1 d P A 1
C21A C 0.3051(3) 0.13492(6) 0.16532(10) 0.0182(6) Uani 0.31(5) 1 d P A 1
H1A H 0.3246 0.1731 0.1545 0.022 Uiso 0.31(5) 1 calc PR A 1
S1B S 0.1524(5) 0.02866(11) 0.16754(18) 0.0240(11) Uani 0.299(16) 1 d P A 2
C21B C 0.1524(5) 0.02866(11) 0.16754(18) 0.0240(11) Uani 0.69(5) 1 d P A 2
H1B H 0.0631 -0.0049 0.1569 0.029 Uiso 0.69(5) 1 calc PR A 2
O1 O 0.0609(6) 0.23597(12) 0.0334(2) 0.0183(7) Uani 1 1 d . . .
O2 O -0.6677(6) 0.05211(12) -0.0820(2) 0.0171(7) Uani 1 1 d . . .
N2 N -0.3009(7) 0.06009(15) 0.0220(2) 0.0146(8) Uani 1 1 d . . .
H2 H -0.2959 0.0258 0.0405 0.018 Uiso 1 1 calc R . .
C15 C -0.1226(8) 0.10056(18) 0.0549(3) 0.0132(9) Uani 1 1 d . A .
C13 C -0.4198(8) 0.13946(18) -0.0545(3) 0.0149(9) Uani 1 1 d . A .
C4 C -1.0224(9) 0.22210(19) -0.3046(3) 0.0200(10) Uani 1 1 d . . .
H4 H -1.1250 0.2389 -0.3533 0.024 Uiso 1 1 calc R . .
C6 C -0.4844(8) 0.18826(18) -0.1040(3) 0.0127(9) Uani 1 1 d . . .
N1 N -0.3058(7) 0.22890(14) -0.0731(2) 0.0144(8) Uani 1 1 d . . .
C1 C -0.6956(8) 0.19488(18) -0.1757(3) 0.0150(10) Uani 1 1 d . . .
C7 C -0.2903(8) 0.28775(18) -0.1008(3) 0.0147(9) Uani 1 1 d . . .
H7A H -0.3328 0.2907 -0.1678 0.018 Uiso 1 1 calc R . .
H7B H -0.1146 0.3008 -0.0867 0.018 Uiso 1 1 calc R . .
C12 C -0.3649(9) 0.4519(2) 0.1202(4) 0.0293(12) Uani 1 1 d . . .
H12A H -0.5338 0.4381 0.0994 0.044 Uiso 1 1 calc R . .
H12B H -0.3467 0.4895 0.0982 0.044 Uiso 1 1 calc R . .
H12C H -0.3417 0.4515 0.1872 0.044 Uiso 1 1 calc R . .
C10 C -0.1799(9) 0.4129(2) -0.0246(3) 0.0227(11) Uani 1 1 d . . .
H10A H -0.0363 0.3910 -0.0429 0.027 Uiso 1 1 calc R . .
H10B H -0.1609 0.4508 -0.0476 0.027 Uiso 1 1 calc R . .
C18 C 0.0866(8) 0.08744(19) 0.1230(3) 0.0172(10) Uani 1 1 d . . .
C17 C -0.1175(8) 0.20738(18) -0.0028(3) 0.0145(9) Uani 1 1 d . A .
C9 C -0.4316(8) 0.38796(19) -0.0722(3) 0.0188(10) Uani 1 1 d . . .
H9A H -0.5758 0.4090 -0.0521 0.023 Uiso 1 1 calc R . .
H9B H -0.4331 0.3928 -0.1392 0.023 Uiso 1 1 calc R . .
C14 C -0.4882(8) 0.08130(18) -0.0443(3) 0.0145(9) Uani 1 1 d . . .
C16 C -0.1944(8) 0.14980(18) 0.0080(3) 0.0138(9) Uani 1 1 d . . .
C2 C -0.8878(8) 0.15582(19) -0.1937(3) 0.0177(10) Uani 1 1 d . . .
H2A H -0.8952 0.1224 -0.1606 0.021 Uiso 1 1 calc R . .
C19 C 0.3800(11) 0.0383(3) 0.2281(4) 0.0364(14) Uani 1 1 d . . .
H19 H 0.4614 0.0095 0.2633 0.044 Uiso 1 1 calc R A 2
C11 C -0.1640(9) 0.4147(2) 0.0820(3) 0.0252(11) Uani 1 1 d . . .
H11A H -0.1831 0.3769 0.1052 0.030 Uiso 1 1 calc R . .
H11B H 0.0057 0.4280 0.1057 0.030 Uiso 1 1 calc R . .
C20 C 0.4704(10) 0.0902(3) 0.2319(4) 0.0369(16) Uani 1 1 d . A .
H20 H 0.576(11) 0.104(3) 0.261(4) 0.05(2) Uiso 1 1 d . . .
C8 C -0.4709(8) 0.32570(18) -0.0515(3) 0.0179(10) Uani 1 1 d . . .
H8A H -0.6478 0.3155 -0.0713 0.021 Uiso 1 1 calc R . .
H8B H -0.4420 0.3196 0.0154 0.021 Uiso 1 1 calc R . .
C3 C -1.0731(9) 0.1714(2) -0.2673(3) 0.0205(10) Uani 1 1 d . . .
H3 H -1.2143 0.1493 -0.2880 0.025 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'
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'
S S 0.1246 0.1234 '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
C4 S2 C1 92.2(2)
C20 S1A C18 94.3(3)
C15 N2 C14 112.5(3)
C16 C15 N2 106.4(4)
C16 C15 C18 132.1(4)
N2 C15 C18 121.5(4)
C6 C13 C16 108.8(4)
C6 C13 C14 143.9(4)
C16 C13 C14 107.3(4)
C3 C4 S2 111.9(3)
N1 C6 C13 107.4(4)
N1 C6 C1 126.5(4)
C13 C6 C1 126.1(4)
C6 N1 C17 111.6(3)
C6 N1 C7 129.5(4)
C17 N1 C7 118.9(3)
C2 C1 C6 123.6(4)
C2 C1 S2 109.9(3)
C6 C1 S2 126.5(3)
N1 C7 C8 112.9(3)
C11 C10 C9 114.7(4)
C15 C18 S1B 126.8(4)
C15 C18 S1A 123.2(4)
S1B C18 S1A 109.9(3)
O1 C17 N1 122.7(4)
O1 C17 C16 133.6(4)
N1 C17 C16 103.7(3)
C8 C9 C10 114.3(4)
O2 C14 N2 122.9(4)
O2 C14 C13 132.3(4)
N2 C14 C13 104.8(4)
C15 C16 C13 109.0(4)
C15 C16 C17 142.4(4)
C13 C16 C17 108.5(4)
C1 C2 C3 113.4(4)
C12 C11 C10 114.0(4)
C19 C20 S1A 115.0(4)
C9 C8 C7 112.6(4)
C4 C3 C2 112.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S2 C4 1.708(5)
S2 C1 1.735(4)
S1A C20 1.624(7)
S1A C18 1.678(5)
S1B C18 1.564(5)
O1 C17 1.228(5)
O2 C14 1.248(5)
N2 C15 1.390(5)
N2 C14 1.392(5)
C15 C16 1.387(6)
C15 C18 1.429(6)
C13 C6 1.388(6)
C13 C16 1.431(6)
C13 C14 1.442(6)
C4 C3 1.359(7)
C6 N1 1.387(5)
C6 C1 1.443(6)
N1 C17 1.435(5)
N1 C7 1.462(5)
C1 C2 1.374(6)
C7 C8 1.528(6)
C12 C11 1.515(7)
C10 C11 1.527(7)
C10 C9 1.540(6)
C17 C16 1.442(6)
C9 C8 1.531(6)
C2 C3 1.412(6)
C19 C20 1.322(8)
