Highly electron deficient diketopyrrolopyrroles.
Humphreys, Joshua; Malagreca, Ferdinando; Hume, Paul A.; Davies, E. Stephen; Argent, Stephen P.; Bradshaw, Tracey D.; Amabilino, David B.; Chemical communications (Cambridge, England) 59 (2023) 1613–1616; doi:10.1039/d2cc06770f

data_7131155
_publ_section_title
;
 Highly electron deficient diketopyrrolopyrroles.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1613
_journal_page_last               1616
_journal_paper_doi               10.1039/d2cc06770f
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C30 H24 N4 O2, 2(C2 H3 N), 2(F6 P)'
_chemical_formula_sum            'C34 H30 F12 N6 O2 P2'
_chemical_formula_weight         844.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-02-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_audit_update_record
;
2022-03-18 deposited with the CCDC.	2023-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.7893(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.56026(5)
_cell_length_b                   13.16435(8)
_cell_length_c                   21.40535(13)
_cell_measurement_reflns_used    28355
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      75.0510
_cell_measurement_theta_min      3.9240
_cell_volume                     1839.17(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'PILATUS3 R 200K Hybrid Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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    -89.00  25.00   0.50    1.00    --    0.00 -57.00 -30.00  228
  2  \w    -89.00  23.00   0.50    1.00    --    0.00 -38.00  30.00  224
  3  \w    -33.00  33.00   0.50    1.00    --    0.00 -82.00-120.00  132
  4  \w     87.00 187.00   0.50    4.00    --   97.70  82.00-120.00  200
  5  \w     74.00 187.00   0.50    4.00    --   97.70  45.00-120.00  226
  6  \w      8.00 135.00   0.50    4.00    --   97.70 -15.00 -90.00  254
  7  \w      8.00 131.00   0.50    4.00    --   97.70 -82.00 150.00  246
  8  \w      8.00 124.00   0.50    4.00    --   97.70 -61.00 -60.00  232
  9  \w      8.00 124.00   0.50    4.00    --   97.70 -61.00 150.00  232
 10  \w     74.00 187.00   0.50    4.00    --   97.70  39.00  -5.29  226
 11  \w      8.00 131.00   0.50    4.00    --   97.70 -82.00  90.00  246
 12  \w      8.00 124.00   0.50    4.00    --   97.70 -61.00 -30.00  232
 13  \w     71.00 187.00   0.50    4.00    --   97.70  61.00  90.00  232
 14  \w      8.00 131.00   0.50    4.00    --   97.70 -82.00 -60.00  246
 15  \w      8.00 131.00   0.50    4.00    --   97.70 -82.00 -30.00  246
 16  \w     79.00 187.00   0.50    4.00    --   97.70  77.00  90.00  216
 17  \w      8.00 131.00   0.50    4.00    --   97.70 -82.00   0.00  246
 18  \w     73.00 187.00   0.50    4.00    --   97.70  30.00   0.00  228
 19  \w    -33.00  33.00   0.50    1.00    --    0.00 -82.00-150.00  132
 20  \w    -33.00  33.00   0.50    1.00    --    0.00 -82.00  30.00  132
 21  \w    -33.00  33.00   0.50    1.00    --    0.00 -82.00 150.00  132
 22  \w     74.00 187.00   0.50    4.00    --   97.70  45.00 -60.00  226
 23  \w     73.00 187.00   0.50    4.00    --   97.70  30.00-180.00  228
 24  \w     71.00 187.00   0.50    4.00    --   97.70  61.00  60.00  232
 25  \w     74.00 187.00   0.50    4.00    --   97.70  45.00 -90.00  226
 26  \w     74.00 187.00   0.50    4.00    --   97.70  45.00-150.00  226
 27  \w     71.00 151.00   0.50    4.00    --   97.70  61.00 120.00  160
 28  \w     74.00 187.00   0.50    4.00    --   97.70  45.00  30.00  226
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'XtalLAB PRO MM007, PILATUS3 R 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0448139000
_diffrn_orient_matrix_UB_12      0.0068345000
_diffrn_orient_matrix_UB_13      0.0719335000
_diffrn_orient_matrix_UB_21      -0.0712913000
_diffrn_orient_matrix_UB_22      0.1115862000
_diffrn_orient_matrix_UB_23      -0.0020819000
_diffrn_orient_matrix_UB_31      -0.2204356000
_diffrn_orient_matrix_UB_32      -0.0346651000
_diffrn_orient_matrix_UB_33      0.0074582000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            40002
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.326
_diffrn_reflns_theta_min         3.948
_diffrn_source                   'rotating anode'
_diffrn_source_type              'MicroMax 007 HF'
_exptl_absorpt_coefficient_mu    2.007
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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            'reddish orange'
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_description       plank
_exptl_crystal_F_000             860
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3779
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0566P)^2^+1.3347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1159
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3581
_reflns_number_total             3779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06770f2.cif
_cod_data_source_block           3-3-2PF6
_cod_depositor_comments
'Adding full bibliography for 7131154--7131156.cif.'
_cod_database_code               7131155
_nottingham_internal_coll_name   DPPFMI
_nottingham_internal_coll_number 18960
_nottingham_internal_coll_client FM/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '1.00, 4.00'
_nottingham_internal_coll_frame_width 0.50
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   11/02/2021
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'XtalLAB PRO, A00000876'
_nottingham_internal_process_date 13/02/2021
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 16/02/2021
_nottingham_internal_solution_user pczspa/pcxfm
_nottingham_internal_refinement_date 16/02/2021
_nottingham_internal_refinement_user pczspa/pcxfm
_nottingham_internal_validation_date 16/02/2021
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 16/02/2021
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C30H24N4O2P2F6
_chemical_oxdiff_usercomment
'DPPFMI #18960 MM-751 FM/DBA fomblin on micromount'
_reflns_odcompleteness_completeness 99.94
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.88 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
3.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              67093
_shelx_hkl_checksum              48612
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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 3.614
_oxdiff_exptl_absorpt_empirical_full_min 0.642