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_7242235
_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         'C28 H32 N2 O4'
_chemical_formula_sum            'C28 H32 N2 O4'
_chemical_formula_weight         460.55
_chemical_name_systematic
'3,6-Bis(4-hydroxyphenyl)-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                 108.388(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3208(2)
_cell_length_b                   8.58917(16)
_cell_length_c                   13.1920(3)
_cell_measurement_reflns_used    6351
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      77.8870
_cell_measurement_theta_min      4.1340
_cell_volume                     1217.25(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'PILATUS3 R 200K Hybrid Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_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    -20.00  89.00   0.50    1.50    --    0.00  38.00 120.00  218
  2  \w      8.00  33.00   0.50    1.50    --    0.00 -82.00  60.00   50
  3  \w    -32.00  20.00   0.50    1.50    --    0.00 -19.00 120.00  104
  4  \w    -67.00 -38.00   0.50    1.50    --    0.00 -19.00 120.00   58
  5  \w     10.00  69.00   0.50    6.00    --   99.10 -38.00-150.00  118
  6  \w     41.00  70.00   0.50    6.00    --   99.10 -38.00-180.00   58
  7  \w     38.00  91.00   0.50    6.00    --   99.10 -57.00-120.00  106
  8  \w     53.00  85.00   0.50    6.00    --   99.10 -57.00  30.00   64
  9  \w     66.00  94.00   0.50    6.00    --   99.10 -57.00 120.00   56
 10  \w     74.00 131.00   0.50    6.00    --   99.10  19.00 -30.00  114
 11  \w    125.00 172.00   0.50    6.00    --   99.10  38.00   0.00   94
 12  \w    150.00 188.00   0.50    6.00    --   99.10  19.00 -30.00   76
 13  \w    115.00 141.00   0.50    6.00    --   99.10  19.00  90.00   52
 14  \w     92.00 132.00   0.50    6.00    --   99.10  82.00  30.00   80
 15  \w     89.00 129.00   0.50    6.00    --   99.10  82.00 -60.00   80
 16  \w     90.00 187.00   0.50    6.00    --   99.10  38.00-120.00  194
 17  \w     89.00 115.00   0.50    6.00    --   99.10  77.00-120.00   52
 18  \w     76.00 149.00   0.50    6.00    --   99.10  38.00  90.00  146
 19  \w     82.00 178.00   0.50    6.00    --   99.10  38.00 120.00  192
 20  \w     67.00  97.00   0.50    6.00    --   99.10  19.00  90.00   60
 21  \w     27.00  69.00   0.50    6.00    --   99.10 -38.00 -90.00   84
 22  \w     16.00 119.00   0.50    6.00    --   99.10 -82.00-150.00  206
 23  \w     27.00  53.00   0.50    6.00    --   99.10 -38.00  90.00   52
 24  \w     19.00  86.00   0.50    6.00    --   99.10 -57.00  60.00  134
 25  \w     15.00  66.00   0.50    6.00    --   99.10 -38.00 120.00  102
 26  \w     11.00  39.00   0.50    6.00    --   99.10 -38.00  30.00   56
 27  \w     10.00  60.00   0.50    6.00    --   99.10 -57.00 120.00  100
 28  \w     29.00  63.00   0.50    6.00    --   99.10 -38.00-120.00   68
;
_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      0.0786771000
_diffrn_orient_matrix_UB_12      0.0081098000
_diffrn_orient_matrix_UB_13      -0.0761927000
_diffrn_orient_matrix_UB_21      0.0815896000
_diffrn_orient_matrix_UB_22      -0.1347568000
_diffrn_orient_matrix_UB_23      0.0610365000
_diffrn_orient_matrix_UB_31      -0.0878472000
_diffrn_orient_matrix_UB_32      -0.1181414000
_diffrn_orient_matrix_UB_33      -0.0748812000
_diffrn_radiation_collimation    'VariMax VHF mirror optic'
_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  0.0400
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13621
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.310
_diffrn_reflns_theta_min         4.115
_diffrn_source                   'rotating anode'
_diffrn_source_current           30
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'MicroMax 007 HF'
_diffrn_source_voltage           40
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       plate
_exptl_crystal_F_000             492
_exptl_crystal_recrystallization_method
'slow evaporation from an acetone solution at low temperature'
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1911 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5021
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0423P)^2^+0.3898P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                4544
_reflns_number_total             5021
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00039j2.cif
_cod_data_source_block           PhOHDPP-N-2MB
_cod_depositor_comments
'Adding full bibliography for 7242233--7242239.cif.'
_cod_original_cell_volume        1217.25(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7242235
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C28 H32 N2 O4'
_chemical_oxdiff_usercomment
'MM-592 OJHAMZ #17321 on a micromount for jh/dba'
_reflns_odcompleteness_completeness 99.96
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C25(H20), C20(H25)
2.b Secondary CH2 refined with riding coordinates:
 C24(H19a,H19b), C27(H22a,H22b), C19(H24a,H24b), C22(H27a,H27b)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H2), C8(H3), C9(H5), C11(H6), C14(H14), C16(H15), C17(H17), C15(H18)
2.d Idealised Me refined as rotating group:
 C26(H21a,H21b,H21c), C28(H23a,H23b,H23c), C21(H26a,H26b,H26c), C23(H28a,H28b,
 H28c)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H1), O4(H4)
;
_shelx_res_checksum              16570
_shelx_hkl_checksum              55588
_nottingham_internal_coll_client JH/DBA
_nottingham_internal_coll_date   30/10/2017
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '6.00, 1.50'
_nottingham_internal_coll_frame_width 0.50
_nottingham_internal_coll_instrument 'XtalLAB PRO, A00000876'
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_name   OJHAMZ
_nottingham_internal_coll_number 17321
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_user   pcxjh6
_nottingham_internal_process_date 31/10/2017
_nottingham_internal_process_user pcxjh6
_nottingham_internal_refinement_date 31/10/2017
_nottingham_internal_refinement_user pcxjh6
_nottingham_internal_self_validation_date 31/10/2017
_nottingham_internal_self_validation_user pcxjh6
_nottingham_internal_solution_date 31/10/2017
_nottingham_internal_solution_user pcxjh6
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id OJHAMZ
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.776
_oxdiff_exptl_absorpt_empirical_full_min 0.701