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_7242237
_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         'C38 H44 N2 O12'
_chemical_formula_sum            'C38 H44 N2 O12'
_chemical_formula_weight         720.75
_chemical_name_systematic
'Di-tert-butyl 3,6-bis(4-((tert-butoxycarbonyl)oxy)phenyl)-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5(1H,4H)-dicarboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 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                 91.113(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4073(9)
_cell_length_b                   10.3312(4)
_cell_length_c                   21.7327(10)
_cell_measurement_reflns_used    3474
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.1520
_cell_measurement_theta_min      4.7340
_cell_volume                     3683.2(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 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.970
_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  34.00   1.00   40.00    --  -38.50  38.00 -90.00   54
  2  \w   -109.00 -12.00   1.00   40.00    --  -38.50 -57.00 -60.00   97
  3  \w    -49.00 -15.00   1.00   40.00    --  -38.50  38.00  90.00   34
  4  \w     68.00 100.00   1.00   40.00    --   42.83 140.00 -65.00   32
  5  \w     33.00  93.00   1.00  180.00    --  104.50 -45.00 -60.00   60
  6  \w     40.00  89.00   1.00  180.00    --  104.50 -30.00-180.00   49
  7  \w     72.00  99.00   1.00  180.00    --  104.50 -94.00 -30.00   27
  8  \w     24.00  52.00   1.00  180.00    --  104.50 -94.00 -30.00   28
  9  \w     50.00  75.00   1.00  180.00    --  104.50 -30.00-150.00   25
 10  \w     26.00 100.00   1.00  180.00    --  104.50 -94.00  60.00   74
 11  \w     29.00 173.00   1.00  180.00    --  104.50   0.00-150.00  144
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas 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      -0.0888677000
_diffrn_orient_matrix_UB_12      -0.0471314000
_diffrn_orient_matrix_UB_13      -0.0062319000
_diffrn_orient_matrix_UB_21      0.0069923000
_diffrn_orient_matrix_UB_22      -0.0007442000
_diffrn_orient_matrix_UB_23      -0.0704758000
_diffrn_orient_matrix_UB_31      0.0296688000
_diffrn_orient_matrix_UB_32      -0.1416397000
_diffrn_orient_matrix_UB_33      0.0026551000
_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  0.0259
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.453
_diffrn_reflns_theta_min         4.069
_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    0.808
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.703
_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    1.300
_exptl_crystal_description       plate
_exptl_crystal_F_000             1528
_exptl_crystal_preparation
'obtained by slow evaporation from a DCM solution'
_exptl_crystal_recrystallization_method
'obtained by slow evaporation from a DCM solution'
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0594P)^2^+3.8360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3131
_reflns_number_total             3595
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00039j2.cif
_cod_data_source_block           PhOBocDPP-N-Boc
_cod_depositor_comments
'Adding full bibliography for 7242233--7242239.cif.'
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               7242237
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C38 H44 N2 O10'
_chemical_oxdiff_usercomment
'OJHALY #16926 GVB-1316 IN FOMBLIN FILM ON A MICROMOUNT FOR JH/DBA'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C19(H19a,H19b,H19c), C12(H12a,H12b,H12c), C13(H13a,H13b,
 H13c), C14(H14a,H14b,H14c), C17(H17a,H17b,H17c)
;
_shelx_res_checksum              83875
_shelx_hkl_checksum              13159
_nottingham_internal_coll_client JH/DBA
_nottingham_internal_coll_date   07/03/2017
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '180.00, 40.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_name   OJHALY
_nottingham_internal_coll_number 16926
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_user   pcxjh6
_nottingham_internal_process_date 21/03/2017
_nottingham_internal_process_user pcxjh6
_nottingham_internal_refinement_date 21/03/2017
_nottingham_internal_refinement_user pcxjh6
_nottingham_internal_self_validation_date 21/03/2017
_nottingham_internal_self_validation_user pcxjh6
_nottingham_internal_solution_date 21/03/2017
_nottingham_internal_solution_user pcxjh6
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id OJHALY
_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 1.246
_oxdiff_exptl_absorpt_empirical_full_min 0.838