#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:13:29 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267003 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/84/7128402.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_7128402
loop_
_publ_author_name
'Mastropasqua Talamo, Maurizio'
'Pop, Flavia'
'Avarvari, Narcis'
_publ_section_title
;
 Straightforward N-alkylation of diketopyrrolopyrroles through the
 Mitsunobu reaction with benzyl, α-branched, and chiral alcohols.
;
_journal_issue                   53
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6514
_journal_page_last               6517
_journal_paper_doi               10.1039/d1cc02472h
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C24 H28 N2 O2 S2'
_chemical_formula_sum            'C24 H28 N2 O2 S2'
_chemical_formula_weight         440.60
_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_method           SHELXL-2018/3
_audit_update_record
;
2021-05-07 deposited with the CCDC.	2021-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.093(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.0653(11)
_cell_length_b                   5.5363(3)
_cell_length_c                   16.2264(10)
_cell_measurement_reflns_used    1875
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.5970
_cell_measurement_theta_min      5.7170
_cell_volume                     1109.14(14)
_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    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material
'WinGX publication routines (Farrugia, V2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector_area_resol_mean 5.1990
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source
'SuperNova(Cu)micro-focus sealed X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4034
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        71.000
_diffrn_reflns_theta_max         72.219
_diffrn_reflns_theta_min         3.580
_exptl_absorpt_coefficient_mu    2.357
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2123
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0455
_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)+(0.0735P)²+0.2070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1807
_reflns_number_total             2123
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02472h2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7128401--7128403.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7128402
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.6617(2) 1.1343(4) 0.77553(15) 0.0690(7) Uani 1 1 d . . . . .
H1 H 0.694624 1.218695 0.826954 0.083 Uiso 1 1 calc R U . . .
C2 C 0.5676(2) 1.1972(4) 0.71643(14) 0.0612(6) Uani 1 1 d . . . . .
H2 H 0.528383 1.332955 0.721878 0.073 Uiso 1 1 calc R U . . .
C3 C 0.53353(19) 1.0373(3) 0.64481(12) 0.0520(5) Uani 1 1 d . . . . .
H3 H 0.468913 1.054683 0.598939 0.062 Uiso 1 1 calc R U . . .
C4 C 0.60598(17) 0.8535(3) 0.65011(11) 0.0484(4) Uani 1 1 d . . . . .
C5 C 0.58864(16) 0.6608(3) 0.58672(10) 0.0434(4) Uani 1 1 d . . . . .
C6 C 0.49154(16) 0.5990(3) 0.52470(10) 0.0428(4) Uani 1 1 d . . . . .
C7 C 0.62166(16) 0.3374(3) 0.50791(11) 0.0452(4) Uani 1 1 d . . . . .
C8 C 0.78271(17) 0.5065(4) 0.62236(12) 0.0528(5) Uani 1 1 d . . . . .
H8A H 0.812253 0.350602 0.614624 0.063 Uiso 1 1 calc R U . . .
H8B H 0.795100 0.527653 0.684208 0.063 Uiso 1 1 calc R U . . .
C9 C 0.84379(18) 0.7030(4) 0.59197(14) 0.0595(5) Uani 1 1 d . . . . .
H9A H 0.809584 0.856287 0.598247 0.071 Uiso 0.474(8) 1 calc R U P A 1
H9B H 0.819378 0.861527 0.604928 0.071 Uiso 0.526(8) 1 calc R U P A 2
C10A C 0.8287(14) 0.676(3) 0.4913(11) 0.089(5) Uani 0.474(8) 1 d . U P A 1
H10A H 0.857504 0.521613 0.481386 0.106 Uiso 0.474(8) 1 calc R U P A 1
H10B H 0.752020 0.678800 0.458099 0.106 Uiso 0.474(8) 1 calc R U P A 1
C10B C 0.9675(16) 0.675(3) 0.6425(11) 0.072(2) Uani 0.526(8) 1 d . U P A 2
H10C H 0.992850 0.523948 0.626090 0.087 Uiso 0.526(8) 1 calc R U P A 2
H10D H 0.978740 0.669300 0.704622 0.087 Uiso 0.526(8) 1 calc R U P A 2
C11A C 0.8850(7) 0.8759(17) 0.4587(6) 0.116(3) Uani 0.474(8) 1 d . . P A 1
H11A H 0.862454 1.029853 0.473833 0.175 Uiso 0.474(8) 1 calc R U P A 1
H11B H 0.866182 0.864536 0.396429 0.175 Uiso 0.474(8) 1 calc R U P A 1
H11C H 0.961975 0.859588 0.485049 0.175 Uiso 0.474(8) 1 calc R U P A 1
C11B C 1.0327(4) 0.8787(11) 0.6243(4) 0.0850(19) Uani 0.526(8) 1 d . . P A 2
H11D H 1.030355 0.871095 0.564635 0.127 Uiso 0.526(8) 1 calc R U P A 2
H11E H 1.106401 0.865441 0.662008 0.127 Uiso 0.526(8) 1 calc R U P A 2
H11F H 1.003060 1.029964 0.634676 0.127 Uiso 0.526(8) 1 calc R U P A 2
C12A C 0.9587(18) 0.713(4) 0.6555(13) 0.091(4) Uani 0.474(8) 1 d . U P A 1
H12A H 0.956814 0.725599 0.713958 0.136 Uiso 0.474(8) 1 calc R U P A 1
H12B H 0.995155 0.851792 0.642637 0.136 Uiso 0.474(8) 1 calc R U P A 1
H12C H 0.996892 0.569366 0.649931 0.136 Uiso 0.474(8) 1 calc R U P A 1
C12B C 0.8265(8) 0.686(2) 0.4970(9) 0.058(3) Uani 0.526(8) 1 d . U P A 2
H12D H 0.851601 0.831809 0.477738 0.087 Uiso 0.526(8) 1 calc R U P A 2
H12E H 0.750706 0.665425 0.465915 0.087 Uiso 0.526(8) 1 calc R U P A 2
H12F H 0.866013 0.550778 0.485980 0.087 Uiso 0.526(8) 1 calc R U P A 2
N1 N 0.66695(13) 0.5045(3) 0.57689(9) 0.0461(4) Uani 1 1 d . . . . .
O1 O 0.67577(12) 0.1816(2) 0.48760(8) 0.0530(4) Uani 1 1 d . . . . .
S1 S 0.71465(5) 0.87918(12) 0.74528(4) 0.0716(2) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C2 C1 S1 111.88(16) . . ?
C2 C1 H1 124.1 . . ?
S1 C1 H1 124.1 . . ?
C1 C2 C3 113.3(2) . . ?
C1 C2 H2 123.3 . . ?
C3 C2 H2 123.3 . . ?
C4 C3 C2 112.8(2) . . ?
C4 C3 H3 123.6 . . ?
C2 C3 H3 123.6 . . ?
C3 C4 C5 123.86(19) . . ?
C3 C4 S1 110.06(14) . . ?
C5 C4 S1 125.98(15) . . ?
C6 C5 N1 107.33(15) . . ?
C6 C5 C4 126.44(17) . . ?
N1 C5 C4 126.23(18) . . ?
C5 C6 C6 109.1(2) . 3_666 ?
C5 C6 C7 142.66(16) . 3_666 ?
C6 C6 C7 108.2(2) 3_666 3_666 ?
O1 C7 N1 122.72(18) . . ?
O1 C7 C6 133.25(18) . 3_666 ?
N1 C7 C6 104.04(14) . 3_666 ?
N1 C8 C9 114.22(15) . . ?
N1 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
N1 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C12B C9 C10B 108.6(7) . . ?
C12B C9 C8 111.9(5) . . ?
C10B C9 C8 108.8(7) . . ?
C8 C9 C12A 108.3(9) . . ?
C8 C9 C10A 111.4(7) . . ?
C12A C9 C10A 117.6(10) . . ?
C8 C9 H9A 106.3 . . ?
C12A C9 H9A 106.3 . . ?
C10A C9 H9A 106.3 . . ?
C12B C9 H9B 109.2 . . ?
C10B C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C11A C10A C9 112.4(13) . . ?
C11A C10A H10A 109.1 . . ?
C9 C10A H10A 109.1 . . ?
C11A C10A H10B 109.1 . . ?
C9 C10A H10B 109.1 . . ?
H10A C10A H10B 107.9 . . ?
C9 C10B C11B 112.3(10) . . ?
C9 C10B H10C 109.1 . . ?
C11B C10B H10C 109.1 . . ?
C9 C10B H10D 109.1 . . ?
C11B C10B H10D 109.1 . . ?
H10C C10B H10D 107.9 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C9 C12A H12A 109.5 . . ?
C9 C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C9 C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C9 C12B H12D 109.5 . . ?
C9 C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C9 C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C5 N1 C7 111.29(16) . . ?
C5 N1 C8 128.48(16) . . ?
C7 N1 C8 120.07(15) . . ?
C1 S1 C4 91.90(11) . . ?
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
C1 C2 1.335(4) . ?
C1 S1 1.713(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.412(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.447(2) . ?
C4 S1 1.728(2) . ?
C5 C6 1.380(3) . ?
C5 N1 1.389(2) . ?
C6 C6 1.418(3) 3_666 ?
C6 C7 1.442(3) 3_666 ?
C7 O1 1.227(2) . ?
C7 N1 1.423(2) . ?
C8 N1 1.450(3) . ?
C8 C9 1.524(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C12B 1.485(14) . ?
C9 C10B 1.563(19) . ?
C9 C12A 1.52(2) . ?
C9 C10A 1.588(18) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10A C11A 1.51(2) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C10B C11B 1.50(2) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 1.2(2) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
C2 C3 C4 C5 177.74(16) . . . . ?
C2 C3 C4 S1 1.0(2) . . . . ?
C3 C4 C5 C6 -15.6(3) . . . . ?
S1 C4 C5 C6 160.53(14) . . . . ?
C3 C4 C5 N1 164.06(16) . . . . ?
S1 C4 C5 N1 -19.8(2) . . . . ?
N1 C5 C6 C6 0.2(2) . . . 3_666 ?
C4 C5 C6 C6 179.97(17) . . . 3_666 ?
N1 C5 C6 C7 179.8(2) . . . 3_666 ?
C4 C5 C6 C7 -0.5(3) . . . 3_666 ?
N1 C8 C9 C12B -57.0(4) . . . . ?
N1 C8 C9 C10B -177.0(6) . . . . ?
N1 C8 C9 C12A 169.7(8) . . . . ?
N1 C8 C9 C10A -59.4(7) . . . . ?
C8 C9 C10A C11A 177.7(8) . . . . ?
C12A C9 C10A C11A -56.5(15) . . . . ?
C12B C9 C10B C11B 64.6(11) . . . . ?
C8 C9 C10B C11B -173.3(7) . . . . ?
C6 C5 N1 C7 -0.06(18) . . . . ?
C4 C5 N1 C7 -179.81(15) . . . . ?
C6 C5 N1 C8 175.31(16) . . . . ?
C4 C5 N1 C8 -4.4(3) . . . . ?
O1 C7 N1 C5 -179.78(15) . . . . ?
C6 C7 N1 C5 -0.12(17) 3_666 . . . ?
O1 C7 N1 C8 4.4(2) . . . . ?
C6 C7 N1 C8 -175.93(14) 3_666 . . . ?
C9 C8 N1 C5 -75.4(2) . . . . ?
C9 C8 N1 C7 99.6(2) . . . . ?
C2 C1 S1 C4 -0.54(18) . . . . ?
C3 C4 S1 C1 -0.30(15) . . . . ?
C5 C4 S1 C1 -176.92(17) . . . . ?
