The effect of rigidity on the emission of quadrupolar strongly polarized dyes
Szymański, Bartosz; Sahoo, Smruti Ranjan; Valiev, Rashid; Vakuliuk, Olena; Łaski, Piotr; Jarzembska, Katarzyna N.; Kamiński, Radosław; Baryshnikov, Glib; Teimouri, Mohammad B.; Gryko, Daniel T.; New Journal of Chemistry 48 (2024) 2416–2420; doi:10.1039/D3NJ05467E

data_7062945
_publ_section_title
;
 The effect of rigidity on the emission of quadrupolar strongly polarized
 dyes
;
_journal_issue                   6
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2416
_journal_page_last               2420
_journal_paper_doi               10.1039/D3NJ05467E
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         '2(C27 H33 N3 O), 0.824(C H2 Cl2)'
_chemical_formula_sum            'C54.83 H67.65 Cl1.65 N6 O2'
_chemical_formula_weight         901.19
_chemical_melting_point          364
_chemical_name_systematic
2,5-bis(4-(2,1,3-benzoxadiazolyl))-1,4-bis(4-dodecylphenyl)-1,4-dihydropyrrolo[3,2-b]pyrrole
_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             2023-07-25
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-08-15 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                78.691(4)
_cell_angle_beta                 88.151(4)
_cell_angle_gamma                87.222(5)
_cell_formula_units_Z            2
_cell_length_a                   8.0413(5)
_cell_length_b                   14.3206(8)
_cell_length_c                   21.6156(8)
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.8710
_cell_measurement_theta_min      2.0290
_cell_volume                     2437.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5373
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_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   -117.00 -30.00   1.00    5.00    --  -40.76 -77.00 120.00   87
  2  \w   -117.00 -30.00   1.00    5.00    --  -40.76 -77.00  60.00   87
  3  \w   -117.00 -30.00   1.00    5.00    --  -40.76 -77.00-180.00   87
  4  \w   -117.00 -30.00   1.00    5.00    --  -40.76 -77.00 -60.00   87
  5  \w    -97.00 -12.00   1.00    5.00    --  -40.76 125.00-180.00   85
  6  \w      8.00  87.00   1.00    5.00    --   40.76  77.00   0.00   79
  7  \w     34.00  82.00   1.00    5.00    --   40.76 -99.00   0.00   48
  8  \w     29.00 106.00   1.00   20.00    --  109.50 -94.00  90.00   77
  9  \w     43.00 108.00   1.00   20.00    --  109.50-111.00-120.00   65
 10  \w     29.00 106.00   1.00   20.00    --  109.50 -94.00 -30.00   77
 11  \w     36.00 139.00   1.00   20.00    --  109.50 -61.00-180.00  103
 12  \w     37.00 137.00   1.00   20.00    --  109.50 -45.00 -60.00  100
 13  \w     78.00 158.00   1.00   20.00    --  109.50  30.00 -30.00   80
 14  \w     78.00 158.00   1.00   20.00    --  109.50  30.00 150.00   80
 15  \w     37.00 137.00   1.00   20.00    --  109.50 -45.00  90.00  100
 16  \w     82.00 158.00   1.00   20.00    --  109.50  45.00-180.00   76
 17  \w     43.00 108.00   1.00   20.00    --  109.50-111.00 -60.00   65
 18  \w     82.00 158.00   1.00   20.00    --  109.50  45.00 -90.00   76
 19  \w     43.00 108.00   1.00   20.00    --  109.50-111.00  30.00   65
 20  \w     78.00 158.00   1.00   20.00    --  109.50  30.00-120.00   80
 21  \w     89.00 146.00   1.00   20.00    --  109.50 178.00 150.00   57
 22  \w     34.00 143.00   1.00   20.00    --  109.50 -77.00  90.00  109
 23  \w     34.00 158.00   1.00   20.00    --  109.50  15.00  90.00  124
 24  \w   -114.00 -54.00   1.00    5.00    --  -40.76-152.00 -99.00   60
 25  \w      8.00  87.00   1.00    5.00    --   40.76  77.00 120.00   79
 26  \w      8.00  87.00   1.00    5.00    --   40.76  77.00-120.00   79
 27  \w      6.00  74.00   1.00    5.00    --   40.76 -77.00  30.00   68
 28  \w      6.00  74.00   1.00    5.00    --   40.76 -77.00 120.00   68
 29  \w      6.00  74.00   1.00    5.00    --   40.76 -77.00 -90.00   68
 30  \w     79.00 158.00   1.00   20.00    --  109.50  61.00  90.00   79
 31  \w     79.00 119.00   1.00   20.00    --  109.50  61.00-120.00   40
 32  \w     79.00 158.00   1.00   20.00    --  109.50  61.00 -90.00   79
 33  \w     79.00 158.00   1.00   20.00    --  109.50  61.00  60.00   79
 34  \w     79.00 158.00   1.00   20.00    --  109.50  61.00  30.00   79
 35  \w     79.00 158.00   1.00   20.00    --  109.50  61.00 -30.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0081641000
_diffrn_orient_matrix_UB_12      -0.1094065000
_diffrn_orient_matrix_UB_13      0.0143152000
_diffrn_orient_matrix_UB_21      0.0214645000
_diffrn_orient_matrix_UB_22      -0.0010567000
_diffrn_orient_matrix_UB_23      -0.0709429000
_diffrn_orient_matrix_UB_31      0.1904779000
_diffrn_orient_matrix_UB_32      -0.0093251000
_diffrn_orient_matrix_UB_33      0.0069062000
_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  0.0645
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            38160
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.726
_diffrn_reflns_theta_min         2.085
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.388
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
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            red
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       needle
_exptl_crystal_F_000             965
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane, isopropanol'
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.092
_refine_diff_density_max         1.271
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     589
_refine_ls_number_reflns         9943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0732
_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^)+(0.1034P)^2^+2.7818P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1985
_refine_ls_wR_factor_ref         0.2260
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7145
_reflns_number_total             9943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj05467e2.cif
_cod_data_source_block           28_12_2022_bsz0047-10_t=100k_01
_cod_depositor_comments          'Adding full bibliography for 7062945.cif.'
_cod_database_code               7062945
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C55H68N6O2Cl2
_shelx_estimated_absorpt_t_max   0.883
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(Cl1)=Sof(Cl2)=Sof(C55)=Sof(H55A)=Sof(H55B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C49(H49A,H49B), C25(H25A,H25B), C51(H51A,H51B), C23(H23A,
 H23B), C19(H19A,H19B), C50(H50A,H50B), C44(H44A,H44B), C48(H48A,H48B),
 C52(H52A,H52B), C24(H24A,H24B), C26(H26A,H26B), C45(H45A,H45B), C46(H46A,H46B),
  C53(H53A,H53B), C22(H22A,H22B), C20(H20A,H20B), C16(H16A,H16B), C47(H47A,
 H47B), C18(H18A,H18B), C43(H43A,H43B), C21(H21A,H21B), C55(H55A,H55B)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C38(H38), C8(H8), C4(H4), C39(H39), C42(H42), C35(H35),
 C15(H15), C14(H14), C2(H2A), C31(H31), C30(H30), C32(H32), C3(H3), C41(H41)
3.c Idealised Me refined as rotating group:
 C54(H54A,H54B,H54C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              67111
_shelx_hkl_checksum              93948
_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 1.728
_oxdiff_exptl_absorpt_empirical_full_min 0.669