Urea-fused and π-extended single-benzene fluorophores with ultralarge Stokes shifts.
Choi, Taehyeon; Kim, Heechan; Kim, Younghun; Lee, Dongwhan; Chemical communications (Cambridge, England) 60 (2024) 9105–9108; doi:10.1039/d4cc03389b

data_7133434
_publ_section_title
;
 Urea-fused and &#x3c0;-extended single-benzene fluorophores with
 ultralarge Stokes shifts.
;
_journal_issue                   68
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9105
_journal_page_last               9108
_journal_paper_doi               10.1039/d4cc03389b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C H Cl3, C25 H30 N6 O'
_chemical_formula_sum            'C26 H31 Cl3 N6 O'
_chemical_formula_weight         549.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-21
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-07-02 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.2310(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.18070(10)
_cell_length_b                   11.62690(10)
_cell_length_c                   19.3144(2)
_cell_measurement_reflns_used    15020
_cell_measurement_temperature    93
_cell_measurement_theta_max      78.8470
_cell_measurement_theta_min      4.4830
_cell_volume                     2673.29(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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_temperature      93
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_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    -49.00 -24.00   0.50    4.41    --    0.00 -21.00  76.00   50
  2  \w      2.00  49.00   0.50    4.41    --    0.00  21.00-116.00   94
  3  \w    130.00 155.00   0.50   15.13    --  105.20  21.00-116.00   50
  4  \w     73.00  99.00   0.50   15.13    --  105.20 -21.00  76.00   52
  5  \w     19.00  62.00   0.50    4.41    --    0.00  57.00 120.00   86
  6  \w    -24.00   2.00   0.50    4.41    --    0.00 -38.00   0.00   52
  7  \w    -21.00   5.00   0.50    4.41    --    0.00 -38.00 -30.00   52
  8  \w    -32.00  88.00   0.50    4.41    --    0.00  77.00  30.00  240
  9  \w    -64.00 -39.00   0.50    4.41    --    0.00 -38.00 -30.00   50
 10  \w    -52.00 -26.00   0.50    4.41    --    0.00 -38.00   0.00   52
 11  \w     76.00 133.00   0.50   15.13    --  105.20 -61.00 -30.00  114
 12  \w     79.00 194.00   0.50   15.13    --  105.20  45.00-120.00  230
 13  \w    103.00 139.00   0.50   15.13    --  105.20 -77.00  90.00   72
 14  \w    126.00 194.00   0.50   15.13    --  105.20  30.00 120.00  136
 15  \w     80.00 105.00   0.50   15.13    --  105.20  30.00 120.00   50
 16  \w     17.00  50.00   0.50   15.13    --  105.20 -61.00 -30.00   66
 17  \w     90.00 132.00   0.50   15.13    --  105.20 -45.00 120.00   84
 18  \w     82.00 113.00   0.50   15.13    --  105.20  45.00-150.00   62
 19  \w     71.00 139.00   0.50   15.13    --  105.20 -77.00 -90.00  136
 20  \w     22.00  66.00   0.50   15.13    --  105.20 -77.00 -90.00   88
 21  \w     17.00  84.00   0.50   15.13    --  105.20 -45.00 120.00  134
 22  \w     24.00  64.00   0.50   15.13    --  105.20 -77.00  90.00   80
 23  \w     38.00 122.00   0.50   15.13    --  105.20 -61.00 -90.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0899050000
_diffrn_orient_matrix_UB_12      -0.0353454000
_diffrn_orient_matrix_UB_13      0.0413081000
_diffrn_orient_matrix_UB_21      -0.0916087000
_diffrn_orient_matrix_UB_22      0.0118414000
_diffrn_orient_matrix_UB_23      -0.0680737000
_diffrn_orient_matrix_UB_31      0.0163595000
_diffrn_orient_matrix_UB_32      -0.1271671000
_diffrn_orient_matrix_UB_33      -0.0178590000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19770
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.414
_diffrn_reflns_theta_min         3.948
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.355
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.223
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.587
_exptl_crystal_size_mid          0.416
_exptl_crystal_size_min          0.357
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5672
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0657
_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^)+(0.1197P)^2^+1.8402P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1816
_refine_ls_wR_factor_ref         0.1841
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5289
_reflns_number_total             5672
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03389b2.cif
_cod_data_source_block           cth-4-202
_cod_depositor_comments          'Adding full bibliography for 7133434.cif.'
_cod_database_code               7133434
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_olex2_refinement_description
;
1. Restrained distances
 N00Q-C00Z \\sim N00Q-C1
 with sigma of 0.02
 C00Z-C010 \\sim C1-C0
 with sigma of 0.02
 N00Q-C010 \\sim N00Q-C0
 with sigma of 0.04
2. Others
 Sof(C0)=Sof(H0A)=Sof(H0B)=Sof(H0C)=Sof(C1)=Sof(H1A)=Sof(H1B)=1-FVAR(1)
 Sof(C00Z)=Sof(H00X)=Sof(H00Y)=Sof(C010)=Sof(H01A)=Sof(H01B)=Sof(H01C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C00S(H00A,H00B), C00T(H00C,H00D), C00U(H00E,H00G), C00Z(H00X,H00Y), C1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 N005(H005), N006(H006), C00F(H00F), C00H(H00H), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P)
3.c Idealised Me refined as rotating group:
 C00V(H00I,H00J,H00Q), C00X(H00R,H00S,H00T), C00Y(H00U,H00V,H00W), C010(H01A,
 H01B,H01C), C0(H0A,H0B,H0C)
;
_shelx_res_checksum              58269
_shelx_hkl_checksum              75271
_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 3.708
_oxdiff_exptl_absorpt_empirical_full_min 0.340