Four polymorphic structures of a symmetric azo dye
Hill, Max T.; Birch-Machin, Mark A.; Sellars, Jonathan D.; Waddell, Paul G.; CrystEngComm 28 (2026) 1781–1790; doi:10.1039/D5CE01159K

data_7251452
_publ_section_title
;
 Four polymorphic structures of a symmetric azo dye
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1781
_journal_page_last               1790
_journal_paper_doi               10.1039/D5CE01159K
_journal_volume                  28
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H22 N2 O4'
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-12
_audit_creation_method
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2025-12-08 deposited with the CCDC.	2026-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.91720(10)
_cell_length_b                   9.6395(2)
_cell_length_c                   50.1648(11)
_cell_measurement_reflns_used    5273
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      73.2820
_cell_measurement_theta_min      3.5200
_cell_volume                     1894.22(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.126a 64-bit (release 11-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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   -137.00-111.00   0.25    1.57    --  -96.07 -95.00   0.00  104
  2  \w    -51.00 -17.00   0.25    1.57    --  -96.07  45.00  30.00  136
  3  \w     14.00  48.00   0.25    0.39    --  -38.83  38.00 -30.00  136
  4  \w    -33.00   8.00   0.25    0.39    --  -38.83  38.00 -30.00  164
  5  \w    -24.00   8.00   0.25    0.39    --  -38.83  13.00 -73.00  128
  6  \w     40.00  66.00   0.25    0.39    --   35.33-178.00   0.00  104
  7  \w     80.00 118.00   0.25    0.39    --   35.33-178.00   0.00  152
  8  \w     28.00  77.00   0.25    1.57    --  104.27-129.00 -91.00  196
  9  \w     43.00 106.00   0.25    1.57    --  111.20-111.00 -90.00  252
 10  \w     34.00 104.00   0.25    1.57    --  104.27-115.00  -8.00  280
 11  \w     -9.00  23.00   0.25    0.39    --   35.33 -13.00 114.00  128
 12  \w     14.00  48.00   0.25    1.57    --  104.27 -45.00 150.00  136
 13  \w     18.00  43.00   0.25    1.57    --  104.27 -45.00 120.00  100
 14  \w    -51.00 -20.00   0.25    0.39    --   35.33 -13.00 114.00  124
 15  \w     45.00  70.00   0.25    1.57    --  111.20 -61.00  60.00  100
 16  \w     49.00 171.00   0.25    1.57    --  111.20  13.00 -73.00  488
 17  \w     71.00  97.00   0.25    0.39    --   35.33 171.00-137.00  104
 18  \w   -100.00 -70.00   0.25    0.39    --  -38.83-142.00  97.00  120
 19  \w     50.00  93.00   0.25    0.39    --   35.58 178.00  90.00  172
 20  \w    -59.00 -13.00   0.25    1.57    --  -96.07  61.00  90.00  184
 21  \w     17.00  43.00   0.25    1.57    --  104.27 -45.00-150.00  104
 22  \w     14.00  45.00   0.25    1.57    --  104.27 -45.00-120.00  124
 23  \w     14.00  39.00   0.25    1.57    --  104.27 -45.00 -90.00  100
 24  \w     21.00  46.00   0.25    1.57    --  111.20 -45.00-180.00  100
 25  \w     27.00  52.00   0.25    1.57    --  111.20 -61.00   0.00  100
 26  \w     21.00  48.00   0.25    1.57    --  111.20 -45.00 -60.00  108
 27  \w     37.00  63.00   0.25    1.57    --  111.20 -77.00 -60.00  104
 28  \w     77.00 103.00   0.25    1.57    --  111.20 -77.00 -60.00  104
 29  \w     27.00  52.00   0.25    1.57    --  111.20 -61.00 -30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0639827000
_diffrn_orient_matrix_UB_12      -0.1279370000
_diffrn_orient_matrix_UB_13      0.0177047000
_diffrn_orient_matrix_UB_21      0.0236173000
_diffrn_orient_matrix_UB_22      -0.0918816000
_diffrn_orient_matrix_UB_23      -0.0250567000
_diffrn_orient_matrix_UB_31      0.3873948000
_diffrn_orient_matrix_UB_32      0.0267913000
_diffrn_orient_matrix_UB_33      -0.0014088000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_number            8816
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.640
_diffrn_reflns_theta_min         3.524
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.698
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.126a (Rigaku Oxford Diffraction, 2024)
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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       plank
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1225 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0582P)^2^+0.0877P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.614
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                3336
_reflns_number_total             3665
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce01159k2.cif
_cod_data_source_block           jds240049_fa_II
_cod_depositor_comments
'Adding full bibliography for 7251450--7251455.cif.'
_cod_database_code               7251452
_chemical_oxdiff_formula         'C19 H21 N1 O6 S1'
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.795
_diffrn_oxdiff_digest_frames
;
01b47cd8c44bbeecc96111008d78cd7a2a04252f643
;
_diffrn_oxdiff_digest_hkl
;
015fbbdc20dc2dd5016bc9e4f8d6679713b33f
;
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              67581
_shelx_shelxl_version_number     2019/1
_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 1.524
_oxdiff_exptl_absorpt_empirical_full_min 0.684