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_7131154
_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         '2(F6 P), C28 H36 N4 O2, 2(H2 O)'
_chemical_formula_sum            'C28 H40 F12 N4 O4 P2'
_chemical_formula_weight         786.58
_chemical_name_systematic
'4,4'-(3,6-Dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(1- hexylpyridin-1-ium)'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-11-23
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2022-03-18 deposited with the CCDC.	2023-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                94.465(7)
_cell_angle_beta                 99.481(8)
_cell_angle_gamma                97.531(6)
_cell_formula_units_Z            2
_cell_length_a                   9.2788(8)
_cell_length_b                   9.8717(7)
_cell_length_c                   19.406(2)
_cell_measurement_reflns_used    2265
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.0120
_cell_measurement_theta_min      4.6470
_cell_volume                     1729.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega -109.00  -12.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000 -180.0000 97

  2 omega  -50.00   34.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000  120.0000 84

  3 omega  -65.00   32.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  -30.0000 97

  4 omega   23.00   98.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       43.3152 -125.0000  120.0000 75

  5 omega    1.00   83.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       43.3152  -99.0000   30.0000 82

  6 omega   82.00  177.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   45.0000  150.0000 95

  7 omega   94.00  178.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  125.0000  -30.0000 84

  8 omega   35.00   98.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -45.0000  -30.0000 63

  9 omega   25.00  109.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -95.0000    0.0000 84

 10 omega   82.00  177.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   45.0000   60.0000 95

 11 omega   31.00   91.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -30.0000  150.0000 60

 12 omega   25.00  109.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -95.0000   90.0000 84

 13 omega   35.00   98.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -45.0000   60.0000 63

 14 omega   35.00   98.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -45.0000 -150.0000 63

 15 omega   82.00  177.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   45.0000  -30.0000 95

 16 omega   25.00  109.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -95.0000  -90.0000 84

 17 omega   35.00  121.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322 -125.0000 -150.0000 86

 18 omega   31.00   90.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -30.0000  -60.0000 59

 19 omega   75.00  175.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   77.0000   90.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      -0.0418636000
_diffrn_orient_matrix_UB_12      0.0372576000
_diffrn_orient_matrix_UB_13      -0.0756192000
_diffrn_orient_matrix_UB_21      0.0105648000
_diffrn_orient_matrix_UB_22      -0.1476847000
_diffrn_orient_matrix_UB_23      -0.0286444000
_diffrn_orient_matrix_UB_31      -0.1645918000
_diffrn_orient_matrix_UB_32      -0.0428915000
_diffrn_orient_matrix_UB_33      0.0025919000
_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  0.0994
_diffrn_reflns_av_unetI/netI     0.1210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16104
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.398
_diffrn_reflns_theta_max         67.398
_diffrn_reflns_theta_min         4.542
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.104
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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 reddish violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       plate
_exptl_crystal_F_000             812
_exptl_crystal_preparation
'obtained by evaporation from a concentrated water: methyl ethyl ketone solution'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: water, methylethylketone'
_exptl_crystal_size_max          0.1867
_exptl_crystal_size_mid          0.1079
_exptl_crystal_size_min          0.0199
_refine_diff_density_max         1.078
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         6212
_refine_ls_number_restraints     361
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1444
_refine_ls_R_factor_gt           0.0867
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1246P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2142
_refine_ls_wR_factor_ref         0.2587
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3507
_reflns_number_total             6212
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06770f2.cif
_cod_data_source_block           4-2-2PF6
_cod_depositor_comments
'Adding full bibliography for 7131154--7131156.cif.'
_cod_database_code               7131154
_nottingham_internal_coll_name   OJHALI
_nottingham_internal_coll_number 15784
_nottingham_internal_coll_client JH/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '60.0000, 240.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pcxjh6
_nottingham_internal_coll_date   17/03/2016
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SN, XDA 017/09'
_nottingham_internal_process_date 21/03/2016
_nottingham_internal_process_user pcxjh6
_nottingham_internal_solution_date 21/03/2016
_nottingham_internal_solution_user pcxjh6
_nottingham_internal_refinement_date 23/11/2021
_nottingham_internal_refinement_user pcxjh6/pczspa
_nottingham_internal_validation_date 23/11/2021
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 23/11/2021
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C28 H36 N4 O2 P2 F12'
_chemical_oxdiff_usercomment
'OJHALI #15784 JHpyridiniumhexyl IN FOMBLIN FILM ON MICROMOUNT FOR JH/DBA'
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.695
_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, All N(H) groups, All O(H,H) groups
2. Restrained distances
 O4-H4A
 0.84 with sigma of 0.02
 N2-H2 = N1-H1
 0.88 with sigma of 0.02
 H4A-H4B
 1.32 with sigma of 0.02
 O4-H4B
 0.84 with sigma of 0.02
 O3-H3A
 0.84 with sigma of 0.02
 H3B-H3A
 1.32 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
P1 \\sim F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim P2 \\sim F7
\\sim F8 \\sim F9 \\sim F10 \\sim F11 \\sim F12: within 3A with sigma of 0.02
and sigma for terminal atoms of 0.04 within 3A
Uanis(F4) \\sim Ueq, Uanis(F6) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 P1, F1, F2, F3, F4, F5, F6, P2, F7, F8, F9, F10, F11, F12
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,
 H14B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B),
 C27(H27A,H27B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C19(H19), C20(H20), C21(H21), C22(H22)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C28(H28A,H28B,H28C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              76011
_shelx_hkl_checksum              14250
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id OJHALI
_olex2_submission_special_instructions 'No special instructions were received'