Synthesis and fluorescence properties of unsymmetrical 1,4-dihydropyrrolo[3,2-b]pyrrole dyes
Kubota, Yasuhiro; Koide, Kenta; Mizuno, Yuka; Nakazawa, Masato; Inuzuka, Toshiyasu; Funabiki, Kazumasa; Sato, Hiroyasu; Matsui, Masaki; New Journal of Chemistry 46 (2022) 1533–1542; doi:10.1039/D1NJ04663B

data_7061150
_publ_section_title
;
 Synthesis and fluorescence properties of unsymmetrical
 1,4-dihydropyrrolo[3,2-b]pyrrole dyes
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1533
_journal_page_last               1542
_journal_paper_doi               10.1039/D1NJ04663B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C20 H25 N3 O2'
_chemical_formula_sum            'C20 H25 N3 O2'
_chemical_formula_weight         339.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-22
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_audit_update_record
;
2021-11-24 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.747(3)
_cell_angle_beta                 96.017(3)
_cell_angle_gamma                93.379(2)
_cell_formula_units_Z            4
_cell_length_a                   10.6244(3)
_cell_length_b                   12.3177(3)
_cell_length_c                   14.0897(6)
_cell_measurement_reflns_used    14435
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      75.1560
_cell_measurement_theta_min      3.1490
_cell_volume                     1830.20(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.944
_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     33.00  95.00   0.50    0.50    --   67.84   0.00 150.00  124
  2  \w     48.00  73.00   0.50    0.50    --   67.84-135.00-115.00   50
  3  \w     41.00  66.00   0.50    0.50    --   69.39-135.00-115.00   50
  4  \w     46.00 109.00   0.50    0.50    --   67.84  15.00-120.00  126
  5  \w     33.00  94.00   0.50    0.50    --   67.84   0.00-150.00  122
  6  \w     37.00  82.00   0.50    0.50    --   69.39-134.00  64.00   90
  7  \w     28.00  63.00   0.50    0.50    --   67.84-125.00 120.00   70
  8  \w     39.00  64.00   0.50    0.50    --   67.84-134.00  64.00   50
  9  \w     32.00  77.00   0.50    0.50    --   67.84-125.00  30.00   90
 10  \w     32.00  96.00   0.50    0.50    --   69.39-125.00   0.00  128
 11  \w   -119.00 -76.00   0.50    0.50    --  -80.25-135.00-115.00   86
 12  \w   -106.00 -57.00   0.50    0.50    --  -80.25 -15.00 -90.00   98
 13  \w   -111.00 -84.00   0.50    0.50    --  -69.93 -15.00-180.00   54
 14  \w    -78.00 -43.00   0.50    0.50    --  -69.93 -15.00-180.00   70
 15  \w   -102.00 -55.00   0.50    0.50    --  -80.25 -15.00-180.00   94
 16  \w    -88.00 -61.00   0.50    0.50    --  -80.25 -15.00-150.00   54
 17  \w    -86.00 -58.00   0.50    0.50    --  -80.25 -15.00   0.00   56
 18  \w   -122.00 -92.00   0.50    0.50    --  -80.25 -15.00   0.00   60
 19  \w    -89.00 -59.00   0.50    0.50    --  -80.25 -15.00 120.00   60
 20  \w    -98.00 -71.00   0.50    0.50    --  -80.25   0.00 -90.00   54
 21  \w    -85.00 -52.00   0.50    0.50    --  -69.93   0.00-150.00   66
 22  \w    -80.00 -53.00   0.50    0.50    --  -80.25   0.00-150.00   54
 23  \w   -111.00 -53.00   0.50    0.50    --  -80.25 135.00 -49.00  116
 24  \w    -88.00 -63.00   0.50    0.50    --  -68.75 135.00 -49.00   50
 25  \w    -80.00 -51.00   0.50    0.50    --  -68.75 125.00-180.00   58
 26  \w    -95.00 -65.00   0.50    0.50    --  -68.75 125.00  30.00   60
 27  \w    -88.00 -63.00   0.50    0.50    --  -68.75 134.00 130.00   50
 28  \w   -100.00 -70.00   0.50    0.50    --  -69.93 134.00 130.00   60
 29  \w   -110.00 -70.00   0.50    0.50    --  -80.25 134.00 130.00   80
 30  \w    -92.00 -32.00   0.50    0.50    --  -68.75 125.00  90.00  120
 31  \w   -103.00 -41.00   0.50    0.50    --  -80.25 125.00 120.00  124
 32  \w   -106.00 -38.00   0.50    0.50    --  -80.25 125.00  60.00  136
 33  \w    -96.00 -45.00   0.50    0.50    --  -69.93 125.00   0.00  102
 34  \w   -106.00 -45.00   0.50    0.50    --  -80.25 125.00 -90.00  122
 35  \w    -95.00 -62.00   0.50    0.50    --  -68.75 125.00-120.00   66
 36  \w    -66.00 -41.00   0.50    0.50    --  -80.25 125.00-150.00   50
 37  \w   -103.00 -39.00   0.50    0.50    --  -80.25 125.00-180.00  128
 38  \w   -106.00 -80.00   0.50    0.50    --  -80.25 125.00-120.00   52
 39  \w   -100.00 -35.00   0.50    0.50    --  -75.44 123.00-142.40  130
 40  \w   -102.00 -76.00   0.50    0.50    --  -80.25 125.00   0.00   52
 41  \w    -63.00 -38.00   0.50    0.50    --  -80.25 125.00   0.00   50
 42  \w    -63.00 -33.00   0.50    0.50    --  -75.44 124.00  63.79   60
 43  \w   -100.00 -75.00   0.50    0.50    --  -75.44 124.00  63.79   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0471372000
_diffrn_orient_matrix_UB_12      0.1143233000
_diffrn_orient_matrix_UB_13      0.0146007000
_diffrn_orient_matrix_UB_21      -0.0223624000
_diffrn_orient_matrix_UB_22      0.0127016000
_diffrn_orient_matrix_UB_23      -0.1089913000
_diffrn_orient_matrix_UB_31      -0.1364399000
_diffrn_orient_matrix_UB_32      -0.0497150000
_diffrn_orient_matrix_UB_33      0.0003660000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26401
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.496
_diffrn_reflns_theta_min         3.154
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.35a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.017
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.068
_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     459
_refine_ls_number_reflns         7268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1065P)^2^+0.6744P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1694
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6589
_reflns_number_total             7268
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj04663b2.cif
_cod_data_source_block           p5
_cod_depositor_comments
'Adding full bibliography for 7061149--7061150.cif.'
_cod_database_code               7061150
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.899
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C17'(H17C,H17D), C19'(H19C,H19D), C9(H9A,H9B), C9'(H9'A,H9'B),
  C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N1'(H1'), N1(H1), C6'(H6'), C12(H12), C16(H16), C15'(H15'), C15(H15),
 C3'(H3'), C6(H6), C13(H13), C3(H3), C13'(H13'), C16'(H16'), C12'(H12')
2.c Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C), C1(H1A,H1B,H1C), C18'(H18D,H18E,H18F), C20(H20A,H20B,
 H20C), C10(H10A,H10B,H10C), C20'(H20D,H20E,H20F), C10'(H10D,H10E,H10F),
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              77114
_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 1.713
_oxdiff_exptl_absorpt_empirical_full_min 0.591