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_7242238
_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_formula_moiety         'C30 H36 N2 O4'
_chemical_formula_sum            'C30 H36 N2 O4'
_chemical_formula_weight         488.61
_chemical_name_systematic
'2,5-Dihexyl-3,6-bis(4-hydroxyphenyl)-2,5-dihydropyrrolo[3,4- c]pyrrole-1,4-dione'
_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   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                76.61(2)
_cell_angle_beta                 85.29(2)
_cell_angle_gamma                76.64(2)
_cell_formula_units_Z            1
_cell_length_a                   5.2797(14)
_cell_length_b                   7.831(2)
_cell_length_c                   16.028(3)
_cell_measurement_reflns_used    453
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.2930
_cell_measurement_theta_min      5.7010
_cell_volume                     626.9(3)
_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                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.953
_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    -47.00 -15.00   1.00   30.00    --  -43.56 125.00 -60.00   32
  2  \w    -94.00 -51.00   1.00   30.00    --  -43.56 125.00 -60.00   43
  3  \w    -27.00  65.00   1.00   30.00    --   43.56 -38.00  90.00   92
  4  \w     16.00 119.00   1.00   30.00    --   43.56  19.00 -90.00  103
  5  \w     69.00 109.00   1.00  120.00    --  103.00 -94.00  60.00   40
  6  \w     31.00  70.00   1.00  120.00    --  103.00 -77.00 -90.00   39
  7  \w     38.00  72.00   1.00  120.00    --  103.00-125.00-120.00   34
  8  \w     31.00  84.00   1.00  120.00    --  103.00 -30.00  90.00   53
  9  \w     37.00  63.00   1.00  120.00    --  103.00 -45.00  30.00   26
 10  \w     26.00  66.00   1.00  120.00    --  103.00 -94.00  60.00   40
 11  \w    114.00 178.00   1.00  120.00    --  103.00  15.00  30.00   64
 12  \w     79.00 133.00   1.00  120.00    --  103.00 -77.00 120.00   54
 13  \w     88.00 126.00   1.00  120.00    --  103.00 -77.00 -90.00   38
 14  \w     44.00  70.00   1.00  120.00    --  103.00 -77.00 120.00   26
 15  \w     87.00 112.00   1.00  120.00    --  103.00-125.00-120.00   25
 16  \w     69.00  95.00   1.00  120.00    --  103.00  15.00  30.00   26
 17  \w     35.00  70.00   1.00  120.00    --  103.00 -30.00 -60.00   35
 18  \w     56.00 106.00   1.00  120.00    --  103.00 -94.00 -60.00   50
 19  \w     44.00  87.00   1.00  120.00    --  103.00 -30.00  30.00   43
 20  \w     33.00 119.00   1.00  120.00    --  103.00 -15.00-180.00   86
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_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      -0.0736011000
_diffrn_orient_matrix_UB_12      -0.1808266000
_diffrn_orient_matrix_UB_13      0.0035258000
_diffrn_orient_matrix_UB_21      -0.0193642000
_diffrn_orient_matrix_UB_22      0.0471240000
_diffrn_orient_matrix_UB_23      -0.0983944000
_diffrn_orient_matrix_UB_31      0.2902338000
_diffrn_orient_matrix_UB_32      -0.0895836000
_diffrn_orient_matrix_UB_33      -0.0087561000
_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  0.1408
_diffrn_reflns_av_unetI/netI     0.2050
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4095
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.579
_diffrn_reflns_theta_min         5.677
_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    0.683
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.887
_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 orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       plate
_exptl_crystal_F_000             262
_exptl_crystal_recrystallization_method
'grown by slow evaporation from a concentrated THF solution'
_exptl_crystal_size_max          0.141
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.1663
_refine_ls_R_factor_gt           0.0880
_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^)+(0.0180P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.2184
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1189
_reflns_number_total             2419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00039j2.cif
_cod_data_source_block           PhOHDPP-N-Hex
_cod_depositor_comments
'Adding full bibliography for 7242233--7242239.cif.'
_cod_original_cell_volume        627.0(3)
_cod_database_code               7242238
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H36 O4 N2'
_chemical_oxdiff_usercomment
'OJHALZ #16971 GVA-1215 FOMBLIN ON MICROMOUNT FOR JH/DBA'
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.910
_reflns_odcompleteness_completeness 98.89
_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 Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C11(H11a,H11b), C12(H12a,H12b), C13(H13a,H13b), C14(H14a,H14b)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H2), C6(H3), C5(H5), C7(H6)
2.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H1)
;
_shelx_res_checksum              24110
_shelx_hkl_checksum              19169
_nottingham_internal_coll_client JH/DBA
_nottingham_internal_coll_date   21/03/2017
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '30.00, 120.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_name   OJHALZ
_nottingham_internal_coll_number 16971
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_user   pcxjh6
_nottingham_internal_process_date 27/03/2017
_nottingham_internal_process_user pcxjh6
_nottingham_internal_refinement_date 27/03/2017
_nottingham_internal_refinement_user pcxjh6
_nottingham_internal_self_validation_date 03/06/2019
_nottingham_internal_self_validation_user pcxjh6
_nottingham_internal_solution_date 27/03/2017
_nottingham_internal_solution_user pcxjh6
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id OJHALZ
_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 1.629
_oxdiff_exptl_absorpt_empirical_full_min 0.539