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_7242236
_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         'C40 H52 N2 O6'
_chemical_formula_sum            'C40 H52 N2 O6'
_chemical_formula_weight         656.83
_chemical_name_systematic
2,5-Dihexyl-3,6-bis(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-11-07
_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                 96.470(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.4391(17)
_cell_length_b                   15.1213(15)
_cell_length_c                   9.5874(8)
_cell_measurement_reflns_used    5096
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.2210
_cell_measurement_theta_min      4.6050
_cell_volume                     1791.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.960
_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    -65.00  32.00   1.00   13.00    --  -38.50  57.00 150.00   97
  2  \w    -94.00  -2.00   1.00   13.00    --  -38.50 125.00 -90.00   92
  3  \w   -117.00  -2.00   1.00   13.00    --  -38.50 -19.00  90.00  115
  4  \w    -75.00  40.00   1.00   13.00    --  -38.50  19.00  90.00  115
  5  \w     16.00 113.00   1.00   13.00    --   43.13  57.00 150.00   97
  6  \w     21.00 116.00   1.00   13.00    --   43.13  38.00-180.00   95
  7  \w     12.00 117.00   1.00   13.00    --   43.13  77.00-150.00  105
  8  \w     33.00  91.00   1.00   52.00    --  107.38 -30.00 150.00   58
  9  \w     83.00 178.00   1.00   52.00    --  107.38  45.00 150.00   95
 10  \w     80.00 110.00   1.00   52.00    --  107.38  61.00-180.00   30
 11  \w    116.00 177.00   1.00   52.00    --  107.38  77.00  90.00   61
 12  \w     80.00 107.00   1.00   52.00    --  107.38  61.00 150.00   27
 13  \w    117.00 144.00   1.00   52.00    --  107.38  45.00-150.00   27
 14  \w     94.00 175.00   1.00   52.00    --  107.38 125.00 -90.00   81
 15  \w     76.00 103.00   1.00   52.00    --  107.38  77.00  90.00   27
 16  \w     76.00 102.00   1.00   52.00    --  107.38  77.00 150.00   26
 17  \w    140.00 170.00   1.00   52.00    --  107.38  77.00-180.00   30
 18  \w     77.00 104.00   1.00   52.00    --  107.38  77.00-180.00   27
 19  \w     34.00  83.00   1.00   52.00    --  107.38 -30.00-150.00   49
 20  \w    104.00 178.00   1.00   52.00    --  107.38 125.00-120.00   74
 21  \w    112.00 177.00   1.00   52.00    --  107.38  77.00 150.00   65
 22  \w    131.00 158.00   1.00   52.00    --  107.38  61.00 120.00   27
 23  \w     76.00 103.00   1.00   52.00    --  107.38  77.00 120.00   27
 24  \w     53.00  80.00   1.00   52.00    --  107.38 -45.00 120.00   27
 25  \w     84.00 111.00   1.00   52.00    --  107.38  45.00-180.00   27
 26  \w     86.00 113.00   1.00   52.00    --  107.38  45.00-150.00   27
 27  \w     86.00 111.00   1.00   52.00    --  107.38  30.00-180.00   25
 28  \w    152.00 177.00   1.00   52.00    --  107.38  45.00-150.00   25
 29  \w     84.00 114.00   1.00   52.00    --  107.38  45.00 120.00   30
 30  \w     80.00 106.00   1.00   52.00    --  107.38  61.00 120.00   26
 31  \w     80.00 154.00   1.00   52.00    --  107.38  61.00-150.00   74
 32  \w     27.00  94.00   1.00   52.00    --  107.38 -95.00   0.00   67
 33  \w     80.00 122.00   1.00   52.00    --  107.38  61.00  90.00   42
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_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      0.0080897000
_diffrn_orient_matrix_UB_12      0.0415986000
_diffrn_orient_matrix_UB_13      0.1474585000
_diffrn_orient_matrix_UB_21      -0.1227115000
_diffrn_orient_matrix_UB_22      -0.0118553000
_diffrn_orient_matrix_UB_23      0.0018866000
_diffrn_orient_matrix_UB_31      0.0195657000
_diffrn_orient_matrix_UB_32      -0.0922920000
_diffrn_orient_matrix_UB_33      0.0663027000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18027
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.808
_diffrn_reflns_theta_min         3.576
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       plate
_exptl_crystal_F_000             708
_exptl_crystal_recrystallization_method 'Slow evaporation of DCM solution'
_exptl_crystal_size_max          0.456
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3626
_refine_ls_number_restraints     1116
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0850
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1610P)^2^+1.6855P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2398
_refine_ls_wR_factor_ref         0.2621
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2679
_reflns_number_total             3626
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00039j2.cif
_cod_data_source_block           PhOTHPDPP-N-Hex
_cod_depositor_comments
'Adding full bibliography for 7242233--7242239.cif.'
_cod_database_code               7242236
_nottingham_internal_coll_name   OJHALH
_nottingham_internal_coll_number 15783
_nottingham_internal_coll_client JH/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '13.00, 52.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pcxjh6
_nottingham_internal_coll_date   16/03/2016
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SN, XDA 017-09'
_nottingham_internal_process_date 07/11/2019
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 07/11/2019
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 07/11/2019
_nottingham_internal_refinement_user pczspa
_nottingham_internal_validation_date 07/11/2019
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 07/11/2019
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C40 H52 N2 O6'
_chemical_oxdiff_usercomment
'OJHALH #15783 JHlactatehexyl IN FOMBLIN FILM ON MICROMOUNT FOR JH/DBA'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.757
_reflns_odcompleteness_completeness 99.64
_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. Restrained distances
 C26-C25 = C16-C15
 1.5 with sigma of 0.02
 C41-C2 \\sim C31-C2
 with sigma of 0.02
 O37-C62 \\sim O47-C72
 with sigma of 0.02
 O37-C61 \\sim O47-C71
 with sigma of 0.02
 O37-O66 \\sim O47-O76
 with sigma of 0.02
 N1-C21 \\sim N1-C11
 with sigma of 0.02
 C22-C21 \\sim C12-C11
 with sigma of 0.02
 C22-C23 \\sim C13-C12
 with sigma of 0.02
 C24-C23 \\sim C14-C13
 with sigma of 0.02
 C15-C14 \\sim C24-C25
 with sigma of 0.02
 C15-C16 \\sim C26-C25
 with sigma of 0.02
 C11-C13 \\sim C21-C23
 with sigma of 0.02
 C22-C24 \\sim C12-C14
 with sigma of 0.02
 C23-C25 \\sim C13-C15
 with sigma of 0.02
 C16-C14 \\sim C26-C24
 with sigma of 0.02
3. Restrained planarity
 C43, C44, C45, O47
 with sigma of 0.1
 C33, C34, C35, O37
 with sigma of 0.1
 C31, C42, C43, C44, C45, C46
 with sigma of 0.1
 C41, C42, C43, C44, C45, C46
 with sigma of 0.1
 C31, C32, C33, C34, C35, C36
 with sigma of 0.1
 O47, C44, C43, C45
 with sigma of 0.1
 O37, C34, C35, C33
 with sigma of 0.1
 C2, C31, C42, C46
 with sigma of 0.1
 C2, C31, C32, C36
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim C41 \\sim C42 \\sim
C43 \\sim C44 \\sim C45 \\sim C46: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
O47 \\sim O37: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C61 \\sim C62 \\sim C63 \\sim C64 \\sim C65 \\sim O66 \\sim C71 \\sim C72 \\sim
C73 \\sim C74 \\sim C75 \\sim O76 \\sim O47 \\sim O37: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C21 \\sim C22 \\sim
C23 \\sim C24 \\sim C25 \\sim C26: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C11 \\sim H11A \\sim H11B \\sim C12 \\sim H12A \\sim H12B \\sim C13 \\sim H13A
\\sim H13B \\sim C14 \\sim H14A \\sim H14B \\sim C15 \\sim H15A \\sim H15B
\\sim C16 \\sim H16A \\sim H16B \\sim H16C \\sim C21 \\sim H21A \\sim H21B
\\sim C22 \\sim H22A \\sim H22B \\sim C23 \\sim H23A \\sim H23B \\sim C24 \\sim
H24A \\sim H24B \\sim C25 \\sim H25A \\sim H25B \\sim C26 \\sim H26A \\sim H26B
\\sim H26C: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 C31, C32, C33, C34, C35, C36, C41, C42, C43, C44, C45, C46
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C11, C12, C13, C14, C15, C16, C21, C22, C23, C24, C25, C26
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{C11, C12, C13, C14, C15, C16} sigma for 1-2: 0.02, 1-3: 0.04
as
{C21, C22, C23, C24, C25, C26}
{C31, C36, C35, C34, C33, C32} sigma for 1-2: 0.02, 1-3: 0.04
as
{C31, C32, C33, C34, C35, C36}
{C31, C32, C33, C34, C35, C36, O37} sigma for 1-2: 0.02, 1-3: 0.04
as
{C41, C42, C43, C44, C45, C46, O47}
{C61, C62, C63, C64, C65, O66} sigma for 1-2: 0.02, 1-3: 0.04
as
{C71, C72, C73, C74, C75, O76}
7. Others
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=
 Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=
 Sof(H26A)=Sof(H26B)=Sof(H26C)=1-FVAR(1)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=Sof(H13A)=
 Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=
 Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
 Sof(C41)=Sof(C42)=Sof(H42)=Sof(C43)=Sof(H43)=Sof(C44)=Sof(C45)=Sof(H45)=
 Sof(C46)=Sof(H46)=Sof(O47)=Sof(C71)=Sof(H71)=Sof(C72)=Sof(H72A)=Sof(H72B)=
 Sof(C73)=Sof(H73A)=Sof(H73B)=Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(C75)=Sof(H75A)=
 Sof(H75B)=Sof(O76)=1-FVAR(2)
 Sof(C31)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33)=Sof(C34)=Sof(C35)=Sof(H35)=
 Sof(C36)=Sof(H36)=Sof(O37)=Sof(C61)=Sof(H61)=Sof(C62)=Sof(H62A)=Sof(H62B)=
 Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(C65)=Sof(H65A)=
 Sof(H65B)=Sof(O66)=FVAR(2)
8.a Ternary CH refined with riding coordinates:
 C61(H61), C71(H71)
8.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B), C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,H65B),
  C72(H72A,H72B), C73(H73A,H73B), C74(H74A,H74B), C75(H75A,H75B)
8.c Me refined with riding coordinates:
 C16(H16A,H16B,H16C), C26(H26A,H26B,H26C)
8.d Aromatic/amide H refined with riding coordinates:
 C32(H32), C33(H33), C35(H35), C36(H36), C42(H42), C43(H43), C45(H45), C46(H46)
;
_shelx_res_checksum              50114
_shelx_hkl_checksum              65389
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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 2.691
_oxdiff_exptl_absorpt_empirical_full_min 0.754