Azulenes exhibiting solid-state fluorescence: synthesis and photophysics of 2-aryl-6-pyrrolidinylazulenes.
Shoji, Taku; Ariga, Yukino; Ito, Daichi; Ito, Fuyuki; Hamasaki, Atom; Mori, Shigeki; Okujima, Tetsuo; Sekiguchi, Ryuta; Ito, Shunji; Chemical communications (Cambridge, England) 61 (2025) 19481–19484; doi:10.1039/d5cc05926g

data_7135296
_publ_section_title
;
 Azulenes exhibiting solid-state fluorescence: synthesis and photophysics
 of 2-aryl-6-pyrrolidinylazulenes.
;
_journal_issue                   98
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              19481
_journal_page_last               19484
_journal_paper_doi               10.1039/d5cc05926g
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C H Cl3, C26 H26 N2 O6'
_chemical_formula_sum            'C27 H27 Cl3 N2 O6'
_chemical_formula_weight         581.85
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-11-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-11-17 deposited with the CCDC.	2025-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                96.494(4)
_cell_angle_beta                 99.614(4)
_cell_angle_gamma                104.201(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4109(3)
_cell_length_b                   9.9848(6)
_cell_length_c                   18.7960(9)
_cell_measurement_reflns_used    11810
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.7720
_cell_measurement_theta_min      2.2020
_cell_volume                     1312.01(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 7.111
_diffrn_detector_type            'Rigaku Saturn724+ area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -105.00  75.00   0.50    1.00    --  -15.00  45.00   0.00  360
  2  \w   -105.00  75.00   0.50    1.00    --  -15.00  45.00  90.00  360
  3  \w   -105.00  75.00   0.50    1.00    --  -15.00  45.00 180.00  360
  4  \w   -105.00  75.00   0.50    1.00    --  -15.00  45.00 270.00  360
;
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0975998000
_diffrn_orient_matrix_UB_12      0.0253659000
_diffrn_orient_matrix_UB_13      -0.0009528000
_diffrn_orient_matrix_UB_21      -0.0174228000
_diffrn_orient_matrix_UB_22      0.0612516000
_diffrn_orient_matrix_UB_23      -0.0121265000
_diffrn_orient_matrix_UB_31      0.0182532000
_diffrn_orient_matrix_UB_32      0.0334315000
_diffrn_orient_matrix_UB_33      0.0368244000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25568
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.132
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'MicroMax 007'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.396
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         6321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0531P)^2^+0.2284P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1378
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4455
_reflns_number_total             6321
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05926g2.cif
_cod_data_source_block           shojix3
_cod_database_code               7135296
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'O6 N2 C26 H26'
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.954
_reflns_odcompleteness_completeness 89.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.72
_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.a Ternary CH refined with riding coordinates:
 C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C21(H21A,H21B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,
 H25B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C15(H15), C16(H16), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              17619
_shelx_hkl_checksum              69346
_olex2_exptl_crystal_mounting_method loop
_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 1.157
_oxdiff_exptl_absorpt_empirical_full_min 0.893