Solid state structure and properties of phenyl diketopyrrolopyrrole derivatives
Humphreys, Joshua; Pop, Flavia; Hume, Paul A.; Murphy, Alanna S.; Lewis, William; Davies, E. Stephen; Argent, Stephen P.; Amabilino, David B.; CrystEngComm 23 (2021) 1796–1814; doi:10.1039/D1CE00039J

data_7242234
_publ_section_title
;
 Solid state structure and properties of phenyl diketopyrrolopyrrole
 derivatives
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              1796
_journal_page_last               1814
_journal_paper_doi               10.1039/D1CE00039J
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C32 H40 N2 O4'
_chemical_formula_sum            'C32 H40 N2 O4'
_chemical_formula_weight         516.66
_chemical_name_systematic
'2,5-Dihexyl-3,6-bis(4-methoxyphenyl)-2,5-dihydropyrrolo[3,4- c]pyrrole-1,4-dione'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-02 deposited with the CCDC.	2021-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.2530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.4900(2)
_cell_length_b                   10.89170(10)
_cell_length_c                   11.4382(2)
_cell_measurement_reflns_used    14901
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.4960
_cell_measurement_theta_min      5.6370
_cell_volume                     1393.32(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -19.00   6.00   1.00    5.00    --   26.00 110.00-163.17   25
  2  \w     -6.00  20.00   1.00    5.00    --   30.00  92.00 -75.10   26
  3  \w    -38.00  28.00   1.00    5.00    --  -42.12  57.00 -90.00   66
  4  \w   -111.00 -17.00   1.00    5.00    --  -42.12 -57.00 120.00   94
  5  \w    -20.00  21.00   1.00    5.00    --  -42.12  38.00-150.00   41
  6  \w     27.00  96.00   1.00    5.00    --   42.12-125.00-150.00   69
  7  \w     27.00  88.00   1.00    5.00    --   42.12-125.00  90.00   61
  8  \w     15.00  42.00   1.00    5.00    --   46.00  79.00 -61.49   27
  9  \w     13.00  41.00   1.00    5.00    --   46.00  82.00-121.33   28
 10  \w     13.00  40.00   1.00    5.00    --   46.00  82.00 117.81   27
 11  \w     15.00  42.00   1.00    5.00    --   46.00  81.00  14.87   27
 12  \w     79.00 119.00   1.00    5.00    --   54.00  73.00 179.78   40
 13  \w     24.00  66.00   1.00    5.00    --   54.00  73.00 179.78   42
 14  \w     31.00  78.00   1.00    5.00    --   62.00  74.00 -87.73   47
 15  \w     32.00  64.00   1.00    5.00    --   62.00  72.00 -32.47   32
 16  \w     31.00  60.00   1.00    5.00    --   62.00  74.00   2.58   29
 17  \w    108.00 135.00   1.00    5.00    --   62.00  74.00 103.38   27
 18  \w     32.00  61.00   1.00    5.00    --   62.00  74.00 103.38   29
 19  \w     99.00 131.00   1.00    5.00    --   62.00  72.00 -32.47   32
 20  \w     38.00  65.00   1.00    5.00    --   66.00  74.00-118.14   27
 21  \w     99.00 131.00   1.00    5.00    --   66.00  70.00-150.78   32
 22  \w     37.00  66.00   1.00    5.00    --   66.00  70.00-150.78   29
 23  \w     53.00 121.00   1.00    5.00    --   70.00  53.00 -58.44   68
 24  \w     39.00  66.00   1.00    5.00    --   70.00  74.00  40.17   27
 25  \w     48.00  75.00   1.00    5.00    --   70.00  63.00  11.90   27
 26  \w     39.00  70.00   1.00    5.00    --   70.00  74.00 138.23   31
 27  \w     49.00  75.00   1.00   20.00    --   78.00  68.00-105.10   26
 28  \w     49.00  89.00   1.00   20.00    --   78.00  71.00  57.71   40
 29  \w     54.00  81.00   1.00   20.00    --   78.00  62.00 145.31   27
 30  \w     56.00  83.00   1.00   20.00    --   82.00  60.00  22.55   27
 31  \w    114.00 171.00   1.00   20.00    --  101.44  61.00-120.00   57
 32  \w     75.00 103.00   1.00   20.00    --  101.44  61.00-120.00   28
 33  \w     78.00 147.00   1.00   20.00    --  101.44  45.00 150.00   69
 34  \w     29.00 113.00   1.00   20.00    --  101.44-125.00  30.00   84
 35  \w    139.00 166.00   1.00   20.00    --  101.44  61.00  60.00   27
 36  \w     32.00  93.00   1.00   20.00    --  101.44 -61.00-120.00   61
 37  \w     77.00 104.00   1.00   20.00    --  101.44  61.00  60.00   27
 38  \w     75.00 102.00   1.00   20.00    --  101.44  61.00 -90.00   27
 39  \w     75.00 136.00   1.00   20.00    --  101.44  61.00   0.00   61
 40  \w    121.00 171.00   1.00   20.00    --  101.44  61.00 -30.00   50
 41  \w     43.00 112.00   1.00   20.00    --  101.44-125.00-180.00   69
 42  \w     32.00  72.00   1.00   20.00    --  101.44 -45.00 -30.00   40
 43  \w     75.00 152.00   1.00   20.00    --  101.44  61.00-180.00   77
 44  \w    112.00 167.00   1.00   20.00    --  101.44  61.00-150.00   55
 45  \w     75.00 102.00   1.00   20.00    --  101.44  61.00-150.00   27
 46  \w     75.00 107.00   1.00   20.00    --  101.44  61.00 -30.00   32
 47  \w     93.00 120.00   1.00   20.00    --  101.44 -77.00-180.00   27
 48  \w     81.00 113.00   1.00   20.00    --  101.44-125.00 -90.00   32
 49  \w     29.00  62.00   1.00   20.00    --  101.44-125.00 -90.00   33
 50  \w    108.00 158.00   1.00   20.00    --  101.44  61.00 -90.00   50
 51  \w     28.00  92.00   1.00   20.00    --  101.44 -77.00-180.00   64
 52  \w     56.00  92.00   1.00   20.00    --  101.44 -61.00  30.00   36
 53  \w     40.00 102.00   1.00   20.00    --  101.44-125.00  90.00   62
 54  \w     75.00 171.00   1.00   20.00    --  101.44  61.00  90.00   96
 55  \w     75.00 169.00   1.00   20.00    --  101.44  61.00  30.00   94
 56  \w    124.00 168.00   1.00   20.00    --  101.44  61.00 -60.00   44
 57  \w     76.00 103.00   1.00   20.00    --  101.44  61.00 -60.00   27
 58  \w     75.00 103.00   1.00   20.00    --  101.44  61.00 150.00   28
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0561426000
_diffrn_orient_matrix_UB_12      0.0495288000
_diffrn_orient_matrix_UB_13      0.1006428000
_diffrn_orient_matrix_UB_21      -0.1044136000
_diffrn_orient_matrix_UB_22      -0.0911492000
_diffrn_orient_matrix_UB_23      -0.0372127000
_diffrn_orient_matrix_UB_31      0.0702115000
_diffrn_orient_matrix_UB_32      -0.0961491000
_diffrn_orient_matrix_UB_33      0.0873001000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0094
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23084
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.393
_diffrn_reflns_theta_min         3.953
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       plate
_exptl_crystal_F_000             556
_exptl_crystal_recrystallization_method
'obtained by evaporation from a xylene solution'
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2749
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+0.4855P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2607
_reflns_number_total             2749
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00039j2.cif
_cod_data_source_block           PhOMeDPP-N-Hex
_cod_depositor_comments
'Adding full bibliography for 7242233--7242239.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7242234
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C32H40N2O4
_chemical_oxdiff_usercomment
'OJHALJ #16032 GVA-1825 JH/DBA fomblin micromount'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00D(H00C,H00D), C00E(H00E,H00F), C00F(H00G,H00H), C00G(H00I,H00J), C00H(H00K,
 H00L)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00A(H00A), C00B(H00B)
2.c Idealised Me refined as rotating group:
 C00I(H00M,H00N,H00O), C00J(H00P,H00Q,H00R)
;
_shelx_res_checksum              131
_shelx_hkl_checksum              43670
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.156
_oxdiff_exptl_absorpt_empirical_full_min 0.861