#------------------------------------------------------------------------------
#$Date: 2021-03-05 03:43:19 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262555 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/22/7242233.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7242233
loop_
_publ_author_name
'Humphreys, Joshua'
'Pop, Flavia'
'Hume, Paul A.'
'Murphy, Alanna S.'
'Lewis, William'
'Davies, E. Stephen'
'Argent, Stephen P.'
'Amabilino, David B.'
_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
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -60.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000    0.0000    0.0000 175

#__ type_ start__ end____ width___ exp.time_
  2 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000    0.0000 120

#__ type_ start__ end____ width___ exp.time_
  3 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000  120.0000 120

#__ type_ start__ end____ width___ exp.time_
  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       'ω 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/[σ²(Fo²)+(0.0510P)²+0.4128P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.66246(14) 0.63652(3) 0.28733(8) 0.02519(18) Uani 1 1 d . . . . .
O1 O 1.12174(15) 0.59025(4) 0.29833(9) 0.02877(19) Uani 1 1 d . . . . .
O4 O 0.84736(15) 0.68299(3) 0.47684(9) 0.0304(2) Uani 1 1 d . . . . .
N1 N 0.86225(15) 0.58288(4) 0.45223(9) 0.02162(18) Uani 1 1 d . . . . .
C2 C 0.92249(17) 0.49550(4) 0.54860(10) 0.01981(19) Uani 1 1 d . . . . .
C3 C 0.78793(17) 0.54341(4) 0.54893(10) 0.0200(2) Uani 1 1 d . . . . .
C1 C 1.03893(18) 0.56143(4) 0.38689(11) 0.0220(2) Uani 1 1 d . . . . .
C009 C 0.78950(18) 0.64046(4) 0.40913(11) 0.0219(2) Uani 1 1 d . . . . .
C4 C 0.60673(18) 0.55334(4) 0.62776(11) 0.0219(2) Uani 1 1 d . . . . .
C5 C 0.55141(19) 0.50979(5) 0.72222(11) 0.0256(2) Uani 1 1 d . . . . .
H5 H 0.632900 0.474845 0.731853 0.031 Uiso 1 1 calc R . . . .
C6 C 0.3815(2) 0.51662(6) 0.80126(12) 0.0293(2) Uani 1 1 d . . . . .
H6 H 0.347799 0.486730 0.865208 0.035 Uiso 1 1 calc R . . . .
C9 C 0.4794(2) 0.60377(5) 0.61484(14) 0.0302(2) Uani 1 1 d . . . . .
H9 H 0.511737 0.633822 0.550919 0.036 Uiso 1 1 calc R . . . .
C7 C 0.2590(2) 0.56746(6) 0.78732(12) 0.0288(2) Uani 1 1 d . . . . .
C8 C 0.3086(2) 0.61057(5) 0.69291(15) 0.0326(3) Uani 1 1 d . . . . .
H8 H 0.224397 0.645004 0.681971 0.039 Uiso 1 1 calc R . . . .
C12 C 0.5825(2) 0.69004(5) 0.20707(12) 0.0293(3) Uani 1 1 d . . . . .
C14 C 0.7723(2) 0.72456(6) 0.16805(15) 0.0375(3) Uani 1 1 d . . . . .
H14A H 0.846110 0.742794 0.254961 0.056 Uiso 1 1 calc GR . . . .
H14B H 0.722444 0.754826 0.097996 0.056 Uiso 1 1 calc GR . . . .
H14C H 0.871279 0.698417 0.125929 0.056 Uiso 1 1 calc GR . . . .
C13 C 0.4391(2) 0.72384(6) 0.29571(16) 0.0384(3) Uani 1 1 d . . . . .
H13A H 0.325663 0.698219 0.322650 0.058 Uiso 1 1 calc GR . . . .
H13B H 0.374711 0.756654 0.239006 0.058 Uiso 1 1 calc GR . . . .
H13C H 0.523760 0.738597 0.383017 0.058 Uiso 1 1 calc GR . . . .
C15 C 0.4525(3) 0.66406(6) 0.07506(15) 0.0445(4) Uani 1 1 d . . . . .
H15A H 0.546864 0.641268 0.020216 0.067 Uiso 1 1 calc GR . . . .
H15B H 0.385906 0.695474 0.014345 0.067 Uiso 1 1 calc GR . . . .
H15C H 0.340851 0.638662 0.105417 0.067 Uiso 1 1 calc GR . . . .
C10 C 0.0210(5) 0.54226(12) 0.9514(3) 0.0325(7) Uani 0.494(4) 1 d . . P A 1
H10A H -0.017112 0.505792 0.900021 0.049 Uiso 0.494(4) 1 calc GR . P A 1
H10B H -0.102933 0.556738 0.995099 0.049 Uiso 0.494(4) 1 calc GR . P A 1
H10C H 0.140185 0.535223 1.026899 0.049 Uiso 0.494(4) 1 calc GR . P A 1
C11 C -0.0265(4) 0.61575(12) 0.8768(3) 0.0376(7) Uani 0.506(4) 1 d . . P A 2
H11A H -0.094053 0.624042 0.778922 0.056 Uiso 0.506(4) 1 calc GR . P A 2
H11B H 0.065376 0.648529 0.911547 0.056 Uiso 0.506(4) 1 calc GR . P A 2
H11C H -0.137580 0.610156 0.940725 0.056 Uiso 0.506(4) 1 calc GR . P A 2
O2 O 0.0996(6) 0.56413(13) 0.8756(4) 0.0336(6) Uani 0.506(4) 1 d . . P A 2
O3 O 0.0836(5) 0.58476(13) 0.8519(3) 0.0288(6) Uani 0.494(4) 1 d . . P A 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C009 O5 C12 120.78(8) . . ?
C3 N1 C1 113.12(8) . . ?
C3 N1 C009 130.95(9) . . ?
C1 N1 C009 115.93(9) . . ?
C2 C2 C1 107.64(11) 3_766 3_766 ?
C3 C2 C2 110.52(11) . 3_766 ?
C3 C2 C1 141.85(10) . 3_766 ?
N1 C3 C4 124.82(9) . . ?
C2 C3 N1 105.12(9) . . ?
C2 C3 C4 130.06(9) . . ?
O1 C1 N1 121.48(9) . . ?
O1 C1 C2 134.93(11) . 3_766 ?
N1 C1 C2 103.60(9) . 3_766 ?
O5 C009 N1 108.62(8) . . ?
O4 C009 O5 129.06(9) . . ?
O4 C009 N1 122.29(9) . . ?
C5 C4 C3 118.49(10) . . ?
C9 C4 C3 124.18(10) . . ?
C9 C4 C5 117.33(11) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.45(11) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 119.98(11) . . ?
C7 C6 H6 120.0 . . ?
C4 C9 H9 119.3 . . ?
C8 C9 C4 121.36(11) . . ?
C8 C9 H9 119.3 . . ?
C8 C7 C6 119.49(11) . . ?
O2 C7 C6 109.38(16) . . ?
O2 C7 C8 131.13(16) . . ?
O3 C7 C6 131.47(16) . . ?
O3 C7 C8 109.04(16) . . ?
C9 C8 C7 120.37(12) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
O5 C12 C14 108.87(10) . . ?
O5 C12 C13 109.51(10) . . ?
O5 C12 C15 101.63(9) . . ?
C14 C12 C15 111.95(12) . . ?
C13 C12 C14 113.78(11) . . ?
C13 C12 C15 110.38(12) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
C7 O2 C11 113.9(3) . . ?
C7 O3 C10 112.6(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C009 1.3136(12) . ?
O5 C12 1.4945(13) . ?
O1 C1 1.2230(13) . ?
O4 C009 1.1958(13) . ?
N1 C3 1.3985(13) . ?
N1 C1 1.4180(15) . ?
N1 C009 1.4399(13) . ?
C2 C2 1.424(2) 3_766 ?
C2 C3 1.3873(14) . ?
C2 C1 1.4470(13) 3_766 ?
C3 C4 1.4465(16) . ?
C4 C5 1.4042(15) . ?
C4 C9 1.4041(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3783(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.3954(18) . ?
C9 H9 0.9500 . ?
C9 C8 1.3769(19) . ?
C7 C8 1.3857(19) . ?
C7 O2 1.373(4) . ?
C7 O3 1.377(4) . ?
C8 H8 0.9500 . ?
C12 C14 1.5125(19) . ?
C12 C13 1.5097(19) . ?
C12 C15 1.5184(17) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 O3 1.434(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 O2 1.426(4) . ?
