Azo-tagged C4N4 fluorophores: unusual overcrowded structures and their application to fluorescent imaging.
Kohei, Miki; Takizawa, Naoki; Tsutsumi, Ryosuke; Xu, Wei; Kumagai, Naoya; Organic & biomolecular chemistry 21 (2023) 2889–2893; doi:10.1039/d3ob00049d

data_7159129
_publ_section_title
;
 Azo-tagged C4N4 fluorophores: unusual overcrowded structures and their
 application to fluorescent imaging.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2889
_journal_page_last               2893
_journal_paper_doi               10.1039/d3ob00049d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         '2(C3 H7 N O), C40 H40 N8'
_chemical_formula_sum            'C46 H54 N10 O2'
_chemical_formula_weight         778.99
_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             2022-01-27
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-01-07 deposited with the CCDC.	2023-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.6430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.83720(10)
_cell_length_b                   23.7847(2)
_cell_length_c                   15.47280(10)
_cell_measurement_reflns_used    38759
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      76.4980
_cell_measurement_theta_min      3.4590
_cell_volume                     4250.65(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (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_temperature      93.15
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_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   -118.00 -39.00   0.50    0.43    --  -48.46 160.00  16.00  158
  2  \w   -120.00 -58.00   0.50    0.43    --  -48.46-160.00 -13.00  124
  3  \w    -93.00 -19.00   0.50    0.43    --  -48.46 118.00-135.00  148
  4  \w     33.00 119.00   0.50    0.43    --   48.46-160.00 -13.00  172
  5  \w     13.00  93.00   0.50    0.43    --   48.46-118.00 138.00  160
  6  \w     52.00 120.00   0.50    0.43    --   48.46 160.00  16.00  136
  7  \w   -135.00 -39.00   0.50    1.12    -- -100.00 160.00  16.00  192
  8  \w   -109.00 -27.00   0.50    1.12    -- -100.00 118.00-135.00  164
  9  \w   -173.00 -87.00   0.50    1.12    -- -100.00-118.00 138.00  172
 10  \w   -158.00 -58.00   0.50    1.12    -- -100.00-160.00 -13.00  200
 11  \w     35.00 109.00   0.50    1.12    --  107.23-118.00 138.00  148
 12  \w     52.00 158.00   0.50    1.12    --  107.23 160.00  16.00  212
 13  \w     35.00 135.00   0.50    1.12    --  107.23-160.00 -13.00  200
 14  \w     81.00 174.00   0.50    1.12    --  107.23 118.00-135.00  186
 15  \w   -120.00 -33.00   0.50    0.43    --  -48.46 -57.00  30.00  174
 16  \w   -120.00 -26.00   0.50    0.43    --  -48.46 -77.00 150.00  188
 17  \w    -20.00  27.00   0.50    0.43    --  -48.46  19.00 120.00   94
 18  \w    -26.00  20.00   0.50    0.43    --   48.46 -19.00 -90.00   92
 19  \w    -26.00  20.00   0.50    0.43    --   48.46 -19.00  90.00   92
 20  \w    -26.00  20.00   0.50    0.43    --   48.46 -19.00  60.00   92
 21  \w    -73.00 -27.00   0.50    1.12    -- -100.00  61.00-180.00   92
 22  \w   -122.00 -31.00   0.50    1.12    -- -100.00 140.00 139.45  182
 23  \w   -109.00 -27.00   0.50    1.12    -- -100.00 125.00 -30.00  164
 24  \w    -70.00 -30.00   0.50    1.12    -- -100.00  61.00-120.00   80
 25  \w   -173.00 -82.00   0.50    1.12    -- -100.00 -65.00  78.87  182
 26  \w   -108.00 -72.00   0.50    1.12    -- -100.00 111.00-141.88   72
 27  \w    -73.00 -48.00   0.50    1.12    -- -100.00  61.00  60.00   50
 28  \w    -73.00 -28.00   0.50    1.12    -- -100.00  61.00  90.00   90
 29  \w    -69.00 -27.00   0.50    1.12    -- -100.00  61.00-150.00   84
 30  \w   -157.00 -89.00   0.50    1.12    -- -100.00 -56.00  47.43  136
 31  \w    148.00 173.00   0.50    1.12    --  107.23  30.00  30.00   50
 32  \w     95.00 122.00   0.50    1.12    --  107.23  30.00  30.00   54
 33  \w     35.00 105.00   0.50    1.12    --  107.23 -95.00 -60.00  140
 34  \w    149.00 174.00   0.50    1.12    --  107.23  45.00 -60.00   50
 35  \w    103.00 130.00   0.50    1.12    --  107.23  45.00 -60.00   54
 36  \w     95.00 158.00   0.50    1.12    --  107.23  30.00-150.00  126
 37  \w    135.00 174.00   0.50    1.12    --  107.23  45.00-150.00   78
 38  \w    101.00 127.00   0.50    1.12    --  107.23  45.00-150.00   52
 39  \w     65.00 105.00   0.50    1.12    --  107.23 -95.00   0.00   80
 40  \w     36.00  67.00   0.50    1.12    --  107.23 -61.00 120.00   62
 41  \w     96.00 172.00   0.50    1.12    --  107.23  30.00 150.00  152
 42  \w     36.00  83.00   0.50    1.12    --  107.23 -95.00 150.00   94
 43  \w     56.00  97.00   0.50    1.12    --  107.23 -77.00 -60.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-Custom'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0161332000
_diffrn_orient_matrix_UB_12      -0.0641124000
_diffrn_orient_matrix_UB_13      -0.0050156000
_diffrn_orient_matrix_UB_21      0.0460398000
_diffrn_orient_matrix_UB_22      -0.0019912000
_diffrn_orient_matrix_UB_23      0.1011340000
_diffrn_orient_matrix_UB_31      -0.1241158000
_diffrn_orient_matrix_UB_32      -0.0089827000
_diffrn_orient_matrix_UB_33      0.0128206000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            80504
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.889
_diffrn_reflns_theta_min         3.467
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       plate
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         8760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0626P)^2^+2.7736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1345
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7622
_reflns_number_total             8760
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00049d2.cif
_cod_data_source_block           exp_705
_cod_depositor_comments
'Adding full bibliography for 7159126--7159129.cif.'
_cod_database_code               7159129
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     '220125_MK_2, 6-Me'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00U(H00U), C00Y(H00Y), C00Z(H00Z), C011(H011), C20(H20), C017(H017),
 C018(H018), C01B(H01S), C01C(H01T), C01E(H01U), C01F(H01V), C01G(H01W),
 C01H(H01X), C21(H21)
2.b X=CH2 refined with riding coordinates:
 N009(H00A,H00B), N00A(H00C,H00D)
2.c Idealised Me refined as rotating group:
 C00X(H00E,H00F,H00G), C010(H01A,H01B,H01C), C012(H01D,H01E,H01F), C015(H01G,
 H01H,H01I), C016(H01J,H01K,H01L), C019(H01M,H01N,H01O), C01A(H01P,H01Q,H01R),
 C01D(H01Z,H,HA), C01I(H01,HB,HC), C01K(H01Y,HD,HE), C01L(H1,HF,HG), C01M(H2,HH,
 HI)
;
_shelx_res_checksum              57923
_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 1.345
_oxdiff_exptl_absorpt_empirical_full_min 0.790