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_7242239
_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_absolute_configuration syn
_chemical_formula_moiety         'C30 H36 N2 O4'
_chemical_formula_sum            'C30 H36 N2 O4'
_chemical_formula_weight         488.61
_chemical_name_systematic
'3,6-Bis(4-methoxyphenyl)-2,5-bis((S)-2-methylbutyl)-2,5- dihydropyrrolo[3,4-c]pyrrole-1,4-dione'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-26 deposited with the CCDC.	2021-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.259(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0360(8)
_cell_length_b                   11.6239(6)
_cell_length_c                   11.4808(10)
_cell_measurement_reflns_used    4896
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.9870
_cell_measurement_theta_min      4.4380
_cell_volume                     1297.2(2)
_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 (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      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
  1 omega  -38.00   30.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000 -180.0000 68

  2 omega  -83.00  -24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000  -30.0000 59

  3 omega  -48.00   33.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000  -60.0000 81

  4 omega  145.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  125.0000  150.0000 32

  5 omega   41.00   92.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -45.0000 -120.0000 51

  6 omega   41.00   76.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -30.0000 -150.0000 35

  7 omega   42.00   98.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -45.0000  150.0000 56

  8 omega   49.00   97.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -45.0000   60.0000 48

  9 omega   39.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -45.0000    0.0000 52

 10 omega   84.00  173.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   45.0000    0.0000 89

 11 omega   85.00  155.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   30.0000  120.0000 70

 12 omega   16.00  113.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   57.0000 -150.0000 97

 13 omega   12.00  117.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   77.0000   90.0000 105

 14 omega    1.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277  -99.0000   60.0000 82

 15 omega   75.00  123.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   77.0000  150.0000 48

 16 omega   61.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   15.0000  -90.0000 117
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      0.1467019000
_diffrn_orient_matrix_UB_12      -0.0447258000
_diffrn_orient_matrix_UB_13      0.0890410000
_diffrn_orient_matrix_UB_21      0.0553646000
_diffrn_orient_matrix_UB_22      0.0802359000
_diffrn_orient_matrix_UB_23      -0.0708654000
_diffrn_orient_matrix_UB_31      0.0223427000
_diffrn_orient_matrix_UB_32      0.0954674000
_diffrn_orient_matrix_UB_33      0.1013672000
_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  0.0395
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8266
_diffrn_reflns_point_group_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.420
_diffrn_reflns_theta_min         4.372
_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    0.660
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.950
_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 orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       plate
_exptl_crystal_F_000             524
_exptl_crystal_recrystallization_method
'grown by evaporation of a concentrated THF solution'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.2434
_exptl_crystal_size_min          0.1397
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1663 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4540
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0525
_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^)+(0.0964P)^2^+0.2300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1411
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_full    0.793
_reflns_Friedel_fraction_max     0.724
_reflns_number_gt                4353
_reflns_number_total             4540
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00039j2.cif
_cod_data_source_block           PhOMeDPP-N-2MB
_cod_depositor_comments
'Adding full bibliography for 7242233--7242239.cif.'
_cod_original_cell_volume        1297.3(2)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7242239
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H36 N2 O4'
_chemical_oxdiff_usercomment
'OJHALA #14636 SN-525 fomblin film on a mount for JH/DBA'
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.807
_reflns_odcompleteness_completeness 99.92
_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 Ternary CH refined with riding coordinates:
 C22(H22), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C24(H24A,H24B), C26(H26A,H26B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C25(H25A,H25B,
 H25C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              53474
_shelx_hkl_checksum              4116
_nottingham_internal_coll_client JH/DBA
_nottingham_internal_coll_date   01/05/2015
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '3.0000, 12.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_instrument 'SN, XDA 017/09'
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_name   OJHALA
_nottingham_internal_coll_number 14636
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_user   pcxjh6
_nottingham_internal_process_date 24/07/2015
_nottingham_internal_process_user pcxjh6
_nottingham_internal_refinement_date 24/08/2015
_nottingham_internal_refinement_user pcxjh6
_nottingham_internal_self_validation_date 03/06/2019
_nottingham_internal_self_validation_user pcxjh6
_nottingham_internal_solution_date 24/08/2015
_nottingham_internal_solution_user pcxjh6
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id OJHALA
_olex2_submission_special_instructions 'No special instructions were received'