Herringbone to cofacial solid state packing via H-bonding in diketopyrrolopyrrole (DPP) based molecular crystals: influence on charge transport
Joydeep Dhar; Durga Prasad Karothu; Satish Patil; Chem.Commun. 51 (2015) 51–; doi:10.1039/C4cc06063F

data_7116145
_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_moiety         'C24 H24 N2 O2'
_chemical_formula_sum            'C24 H24 N2 O2'
_chemical_formula_weight         372.45
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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_date             2013-10-23
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.55(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9724(13)
_cell_length_b                   26.488(6)
_cell_length_c                   14.650(5)
_cell_measurement_reflns_used    483
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      19.9380
_cell_measurement_theta_min      2.6870
_cell_volume                     1916.9(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.0839
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -96.00  -65.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4177  179.0000 -120.0000 31

  2 omega  -83.00  -37.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4177  179.0000    0.0000 46

  3 omega   13.00   43.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       21.4490  -57.0000  -90.0000 30

  4 omega    7.00   94.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       21.4490   37.0000  -60.0000 87

  5 omega  -50.00   -3.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       21.4490  -37.0000    0.0000 47

  6 omega   -9.00   16.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       21.4490   77.0000   90.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0009045000
_diffrn_orient_matrix_UB_12      -0.0125895000
_diffrn_orient_matrix_UB_13      -0.0427524000
_diffrn_orient_matrix_UB_21      -0.0579338000
_diffrn_orient_matrix_UB_22      0.0216064000
_diffrn_orient_matrix_UB_23      -0.0230611000
_diffrn_orient_matrix_UB_31      0.1315230000
_diffrn_orient_matrix_UB_32      0.0095194000
_diffrn_orient_matrix_UB_33      -0.0038191000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.1166
_diffrn_reflns_av_unetI/netI     0.2341
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7995
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.70
_diffrn_source                   'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.850
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.850
_refine_ls_R_factor_all          0.2647
_refine_ls_R_factor_gt           0.0889
_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/[\s^2^(Fo^2^)+(0.0408P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.2099
_reflns_number_gt                1039
_reflns_number_total             3358
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc06063f2.cif
_cod_data_source_block           red
_cod_database_code               7116145
_chemical_oxdiff_formula         'C15 H11 N3 O4 F2'
_reflns_odcompleteness_completeness 88.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H19A,H19B} of C19, {H22A,H22B} of C22, {H21A,H21B} of C21, H16 of C16, H11
  of C11, H15 of C15, H18 of C18, H17 of C17, H7 of C7, H14 of C14, H8 of C8,
  H9 of C9, {H20A,H20B} of C20, H10 of C10, {H23A,H23B} of C23
 At 1.5 times of:
  {H24A,H24B,H24C} of C24
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C20(H20A,H20B), C19(H19A,H19B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C7(H7), C17(H17), C18(H18), C15(H15), C11(H11), C16(H16),
 C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;