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_7131156
_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         'C28 H36 N4 O2, 2(F6 P)'
_chemical_formula_sum            'C28 H36 F12 N4 O2 P2'
_chemical_formula_weight         750.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-12-10
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2022-03-18 deposited with the CCDC.	2023-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 96.9621(18)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   34.9289(7)
_cell_length_b                   9.64811(19)
_cell_length_c                   9.32463(17)
_cell_measurement_reflns_used    6800
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.5070056337
_cell_measurement_theta_min      2.27018366285
_cell_volume                     3119.21(11)
_computing_cell_refinement
'DIALS 2theta refinement, DIALS 2.1.1-gcdd629a7b-release'
_computing_data_reduction
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 2.1.1-gcdd629a7b-release (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.6.366-ga657f9d9-dials-2.1 (Winter, G., 2010)
;
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      100(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'Photon counting pixel array'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed \c 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24129
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         29.477
_diffrn_reflns_theta_min         2.277
_diffrn_source                   'Diamond Light Source Beamline I19-1'
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.9941388463812154
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
CCP4 7.0.078: AIMLESS, version 0.7.4 : 13/12/18
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_description       plank
_exptl_crystal_F_000             1544
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4749
_refine_ls_number_restraints     175
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0436P)^2^+1.0726P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3386
_reflns_number_total             4749
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06770f2.cif
_cod_data_source_block           3-2-2PF6
_cod_depositor_comments
'Adding full bibliography for 7131154--7131156.cif.'
_cod_original_cell_volume        3119.21(7)
_cod_database_code               7131156
_nottingham_internal_coll_name   DPPFMB_C1
_nottingham_internal_coll_number 18572
_nottingham_internal_coll_client FM/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'fine \w scans'
_nottingham_internal_coll_frame_time 0.2
_nottingham_internal_coll_frame_width 0.01
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   26/01/2020
_nottingham_internal_coll_location DLS
_nottingham_internal_coll_instrument i19-EH1
_nottingham_internal_process_date 26/01/2020
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 26/01/2020
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 10/12/2021
_nottingham_internal_refinement_user pczspa
_nottingham_internal_validation_date 10/12/2021
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 10/12/2021
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.982
_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_$1-H1_$1
 0.88 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11)
4.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              31878
_shelx_hkl_checksum              21728
_olex2_submission_special_instructions 'No special instructions were received'