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_7061149
_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         'C10 H12 N2 O2'
_chemical_formula_sum            'C10 H12 N2 O2'
_chemical_formula_weight         192.22
_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
_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
_cell_angle_beta                 90.2250(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.13210(10)
_cell_length_b                   9.99270(10)
_cell_length_c                   15.33430(10)
_cell_measurement_reflns_used    4474
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.6110
_cell_measurement_theta_min      2.8540
_cell_volume                     939.621(19)
_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      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.942
_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     48.00  74.00   0.50    0.05    --   67.84-125.00-120.00   52
  2  \w     26.00  90.00   0.50    0.05    --   67.84-125.00 -30.00  128
  3  \w     38.00  66.00   0.50    0.05    --   67.84   0.00 120.00   56
  4  \w     76.00 102.00   0.50    0.05    --   67.84   0.00 120.00   52
  5  \w    -97.00 -45.00   0.50    0.05    --  -69.93   0.00-120.00  104
  6  \w    -95.00 -57.00   0.50    0.05    --  -68.75 125.00-180.00   76
  7  \w   -102.00 -74.00   0.50    0.05    --  -80.25 125.00-120.00   56
  8  \w    -74.00 -40.00   0.50    0.05    --  -69.93 125.00  90.00   68
  9  \w   -104.00 -57.00   0.50    0.05    --  -80.25 125.00 120.00   94
 10  \w   -104.00 -40.00   0.50    0.05    --  -68.75 -15.00 120.00  128
 11  \w   -119.00 -58.00   0.50    0.05    --  -80.25 -15.00  90.00  122
 12  \w   -111.00 -50.00   0.50    0.05    --  -69.93 -15.00   0.00  122
 13  \w   -121.00 -51.00   0.50    0.05    --  -80.25 -15.00 -30.00  140
 14  \w   -120.00 -64.00   0.50    0.05    --  -80.25 -15.00-150.00  112
;
_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      0.0075209000
_diffrn_orient_matrix_UB_12      0.1211212000
_diffrn_orient_matrix_UB_13      -0.0620455000
_diffrn_orient_matrix_UB_21      -0.2069328000
_diffrn_orient_matrix_UB_22      0.0571201000
_diffrn_orient_matrix_UB_23      0.0428817000
_diffrn_orient_matrix_UB_31      0.1422660000
_diffrn_orient_matrix_UB_32      0.0764009000
_diffrn_orient_matrix_UB_33      0.0663614000
_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  0.0098
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5182
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.749
_diffrn_reflns_theta_min         5.283
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86928
_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    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.184
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0394P)^2^+0.3588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0842
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1799
_reflns_number_total             1848
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj04663b2.cif
_cod_data_source_block           p2
_cod_depositor_comments
'Adding full bibliography for 7061149--7061150.cif.'
_cod_database_code               7061149
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.868
_shelx_estimated_absorpt_t_min   0.773
_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:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              19502
_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 1.286
_oxdiff_exptl_absorpt_empirical_full_min 0.670