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_7159126
_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_absolute_configuration ad
_chemical_formula_moiety         'C48 H32 N8'
_chemical_formula_sum            'C48 H32 N8'
_chemical_formula_weight         720.81
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-22
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.7717(3)
_cell_length_b                   10.3216(2)
_cell_length_c                   30.7588(5)
_cell_measurement_reflns_used    17556
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      76.2770
_cell_measurement_theta_min      2.8700
_cell_volume                     7229.6(2)
_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 0.967
_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   -123.00 -36.00   0.50    0.91    --  -48.46 -28.00 -31.00  174
  2  \w   -173.00 -72.00   0.50    3.68    -- -100.00-140.00 104.00  202
  3  \w   -173.00 -88.00   0.50    3.68    -- -100.00 -95.00 168.00  170
  4  \w    -41.00  25.00   0.50    0.91    --  -48.46  38.00  90.00  132
  5  \w    -41.00  25.00   0.50    0.91    --  -48.46  38.00 -90.00  132
  6  \w     73.00 120.00   0.50    0.91    --   48.46 130.00  -9.00   94
  7  \w    -24.00  41.00   0.50    0.91    --   48.46 -38.00 -60.00  130
  8  \w    -73.00 -27.00   0.50    3.68    -- -100.00  61.00  90.00   92
  9  \w   -112.00 -27.00   0.50    3.68    -- -100.00 125.00-120.00  170
 10  \w    -63.00 -28.00   0.50    3.68    -- -100.00  61.00 120.00   70
 11  \w    -67.00 -30.00   0.50    3.68    -- -100.00  61.00   0.00   74
 12  \w   -173.00 -86.00   0.50    3.68    -- -100.00 -28.00 -31.00  174
 13  \w     78.00 104.00   0.50    3.68    --  107.23 125.00-150.00   52
 14  \w     35.00  73.00   0.50    3.68    --  107.23 -61.00 150.00   76
 15  \w     96.00 173.00   0.50    3.68    --  107.23  15.00-150.00  154
 16  \w     35.00  72.00   0.50    3.68    --  107.23 -61.00 -30.00   74
 17  \w     47.00  72.00   0.50    3.68    --  107.23 -61.00-150.00   50
 18  \w     35.00  60.00   0.50    3.68    --  107.23 -61.00-120.00   50
;
_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      0.1037910000
_diffrn_orient_matrix_UB_12      -0.0163727000
_diffrn_orient_matrix_UB_13      -0.0338004000
_diffrn_orient_matrix_UB_21      -0.1071767000
_diffrn_orient_matrix_UB_22      -0.0188669000
_diffrn_orient_matrix_UB_23      -0.0320067000
_diffrn_orient_matrix_UB_31      -0.0051445000
_diffrn_orient_matrix_UB_32      0.0628747000
_diffrn_orient_matrix_UB_33      -0.0184523000
_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  0.0476
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            51610
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.330
_diffrn_reflns_theta_min         2.873
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72367
_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    1.324
_exptl_crystal_description       plate
_exptl_crystal_F_000             3008
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 4510 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1010
_refine_ls_number_reflns         13834
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0666P)^2^+1.6283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.835
_reflns_number_gt                11491
_reflns_number_total             13834
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00049d2.cif
_cod_data_source_block           exp_719
_cod_depositor_comments
;
Adding full bibliography for 7159126--7159129.cif.

2024-09-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C96 H64 N16'
_cod_original_formula_weight         1441.63
_cod_original_formula_moiety         '2(C48 H32 N8)'
_cod_original_formula_units_Z            4
_cod_database_code               7159126
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     220218_MK_nap
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.884
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Rotating group:
 N00M(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00P(H00P), C00R(H00R), C00S(H00S), C00V(H00V), C00W(H00W),
 C010(H010), C011(H011), C016(H016), C018(H018), C01B(H01B), C01F(H01F),
 C01G(H01G), C01H(H01H), C01I(H01I), C01K(H01K), C01M(H01M), C01N(H01N),
 C01R(H01R), C01U(H01U), C020(H020), C021(H021), C022(H022), C023(H023),
 C025(H025), C026(H026), C027(H027), C028(H028), C02A(H02A), C02C(H02C),
 C02D(H02D), C02E(H02E), C02F(H02F), C02G(H02G), C02I(H02I), C02J(H02J),
 C02K(H02K), C02L(H02L), C02N(H02N), C02O(H02O), C02P(H02P), C02Q(H02Q),
 C02R(H02R), C02S(H02S), C02T(H02T), C02U(H02U), C02V(H02V), C02W(H02W),
 C02X(H02X), C02Y(H02Y), C02Z(H02Z), C030(H030), C031(H031), C032(H032),
 C033(H033), C034(H034)
2.c X=CH2 refined with riding coordinates:
 N001(H00A,H00B), N00B(H00E,H00F), N00F(H00G,H00H)
;
_shelx_res_checksum              68663
_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 1.255
_oxdiff_exptl_absorpt_empirical_full_min 0.823