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_7242233
_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 H32 N2 O8'
_chemical_formula_sum            'C30 H32 N2 O8'
_chemical_formula_weight         548.57
_chemical_name_systematic
'Di-tert-butyl 3,6-bis(4-methoxyphenyl)-1,4-dioxopyrrolo[3,4- c]pyrrole-2,5(1H,4H)-dicarboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-06-03
_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                 96.832(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2882(2)
_cell_length_b                   22.9444(5)
_cell_length_c                   9.3448(2)
_cell_measurement_reflns_used    8463
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.6330
_cell_measurement_theta_min      2.1060
_cell_volume                     1338.68(6)
_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_area_resol_mean 0.0350
_diffrn_detector_type            'PILATUS 2M Hybrid Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details
;
  1 omega  -60.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000    0.0000    0.0000 175

  2 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000    0.0000 120

  3 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000  120.0000 120

  4 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000  240.0000 120
;
_diffrn_measurement_device       'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Kappa Rigaku Saturn724+'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      -0.0241433000
_diffrn_orient_matrix_UB_12      -0.0285752000
_diffrn_orient_matrix_UB_13      -0.0177216000
_diffrn_orient_matrix_UB_21      0.0351238000
_diffrn_orient_matrix_UB_22      -0.0083175000
_diffrn_orient_matrix_UB_23      0.0696570000
_diffrn_orient_matrix_UB_31      -0.1017952000
_diffrn_orient_matrix_UB_32      0.0039069000
_diffrn_orient_matrix_UB_33      0.0186502000
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  Synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16657
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         31.790
_diffrn_reflns_theta_min         3.346
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81695
_exptl_absorpt_correction_type   multi-scan
_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)
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    1.361
_exptl_crystal_description       plate
_exptl_crystal_F_000             580
_exptl_crystal_preparation
'obtained by evaporation from a toluene solution'
_exptl_crystal_recrystallization_method
'Obtained by slow evaporation from a DCM solution'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         4316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0510P)^2^+0.4128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1237
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3523
_reflns_number_total             4316
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00039j2.cif
_cod_data_source_block           PhOMeDPP-N-Boc
_cod_depositor_comments
'Adding full bibliography for 7242233--7242239.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7242233
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C30 H32 N2 O8'
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 96.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.50
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C11)=Sof(H11a)=Sof(H11b)=Sof(H11c)=Sof(O2)=1-FVAR(1)
 Sof(C10)=Sof(H10a)=Sof(H10b)=Sof(H10c)=Sof(O3)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C8(H8)
3.b Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C13(H13a,H13b,H13c), C15(H15a,H15b,H15c), C10(H10a,H10b,
 H10c), C11(H11a,H11b,H11c)
;
_shelx_res_checksum              90765
_shelx_hkl_checksum              5067
_nottingham_internal_coll_client JH/DBA
_nottingham_internal_coll_date   25/6/2015
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time 1.00
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_instrument 'DLS I19'
_nottingham_internal_coll_location DLS
_nottingham_internal_coll_name   OJHALE
_nottingham_internal_coll_number 14887
_nottingham_internal_coll_type   hemi
_nottingham_internal_coll_user   pczwl
_nottingham_internal_process_user pcxjh6
_nottingham_internal_refinement_user pcxjh6/pczwl
_nottingham_internal_solution_user pcxjh6
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id OJHALE
_olex2_submission_special_instructions 'No special instructions were received'