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_7251455
_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 unk
_chemical_formula_moiety         'C22 H22 N2 O4'
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-22
_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                 98.001(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8556(2)
_cell_length_b                   10.0594(3)
_cell_length_c                   21.7173(6)
_cell_measurement_reflns_used    10930
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      76.3170
_cell_measurement_theta_min      2.0390
_cell_volume                     1915.79(9)
_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 0.998
_diffrn_measured_fraction_theta_max 0.920
_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     72.00  97.00   0.50    1.27    --   46.11 130.00  87.00   50
  2  \w     69.00  94.00   0.50    1.27    --   46.11 140.00 -98.00   50
  3  \w     40.00  84.00   0.50    1.27    --   46.11-130.00  16.00   88
  4  \w    -87.00 -62.00   0.50    1.27    --  -47.36 130.00  87.00   50
  5  \w   -119.00 -90.00   0.50    5.07    --  -92.22-130.00  16.00   58
  6  \w   -140.00-115.00   0.50    5.07    --  -92.22-140.00-157.00   50
  7  \w    -73.00 -36.00   0.50    5.07    --  -92.22 140.00 -98.00   74
  8  \w   -115.00 -51.00   0.50    5.07    --  -92.22 130.00  87.00  128
  9  \w     48.00  73.00   0.50    5.07    --   95.82-140.00-157.00   50
 10  \w     21.00 115.00   0.50    5.07    --   95.82-130.00  16.00  188
 11  \w     49.00  74.00   0.50    5.07    --  107.32-130.00  16.00   50
 12  \w     66.00 172.00   0.50    5.07    --  107.32 140.00 -98.00  212
 13  \w     53.00  78.00   0.50    5.07    --  107.32-140.00-157.00   50
 14  \w    -34.00  24.00   0.50    1.27    --   46.11 -19.00   0.00  116
 15  \w    -36.00  13.00   0.50    1.27    --   46.11 -19.00  60.00   98
 16  \w     78.00 103.00   0.50    1.27    --   46.11 125.00 -60.00   50
 17  \w   -120.00 -73.00   0.50    1.27    --  -47.36-125.00-120.00   94
 18  \w    -37.00  33.00   0.50    1.27    --  -47.36  38.00-180.00  140
 19  \w    -35.00  -9.00   0.50    5.07    --  -92.22  30.00  30.00   52
 20  \w   -168.00-122.00   0.50    5.07    --  -92.22-125.00 150.00   92
 21  \w    -35.00  -9.00   0.50    5.07    --  -92.22  30.00  90.00   52
 22  \w    -51.00 -16.00   0.50    5.07    --  -92.22  45.00-150.00   70
 23  \w    -45.00 -19.00   0.50    5.07    --  -92.22  45.00  90.00   52
 24  \w    -51.00 -11.00   0.50    5.07    --  -92.22  45.00-120.00   80
 25  \w    -34.00  -9.00   0.50    5.07    --  -92.22  30.00  60.00   50
 26  \w   -117.00 -87.00   0.50    5.07    --  -92.22-125.00 150.00   60
 27  \w    -34.00  -9.00   0.50    5.07    --  -92.22  30.00 150.00   50
 28  \w     16.00  43.00   0.50    5.07    --   95.82 -45.00 -30.00   54
 29  \w     15.00  40.00   0.50    5.07    --   95.82 -45.00   0.00   50
 30  \w     33.00  71.00   0.50    5.07    --   95.82 -61.00  30.00   76
 31  \w     45.00  71.00   0.50    5.07    --  107.32 -95.00-150.00   52
 32  \w     34.00  79.00   0.50    5.07    --  107.32-125.00 -90.00   90
 33  \w     74.00 103.00   0.50    5.07    --  107.32 -95.00-150.00   58
 34  \w     45.00  71.00   0.50    1.27    --   46.11-140.00-157.00   52
 35  \w    -11.00  19.00   0.50    1.27    --   46.11 -19.00-150.00   60
 36  \w     80.00 122.00   0.50    1.27    --   46.11 125.00  30.00   84
 37  \w    -23.00  16.00   0.50    1.27    --   46.11 -19.00-180.00   78
 38  \w   -102.00 -73.00   0.50    1.27    --  -47.36-125.00  90.00   58
 39  \w    -94.00 -64.00   0.50    5.07    --  -92.22 -77.00  90.00   60
 40  \w    -35.00 -10.00   0.50    5.07    --  -92.22  30.00   0.00   50
 41  \w   -147.00-119.00   0.50    5.07    --  -92.22 -77.00  90.00   56
 42  \w    -41.00 -15.00   0.50    5.07    --  -92.22  45.00 -60.00   52
 43  \w    -35.00 -10.00   0.50    5.07    --  -92.22  30.00 -30.00   50
 44  \w    -35.00 -10.00   0.50    5.07    --  -92.22  30.00-180.00   50
 45  \w    -35.00 -10.00   0.50    5.07    --  -92.22  30.00 120.00   50
 46  \w    -54.00 -21.00   0.50    5.07    --  -92.22 125.00 -30.00   66
 47  \w    -38.00 -12.00   0.50    5.07    --  -92.22  45.00 120.00   52
 48  \w   -111.00 -60.00   0.50    5.07    --  -92.22 125.00 -30.00  102
 49  \w    -87.00 -61.00   0.50    5.07    --  -92.22 -77.00 -90.00   52
 50  \w   -144.00-113.00   0.50    5.07    --  -92.22 -77.00 -90.00   62
;
_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      -0.0266254000
_diffrn_orient_matrix_UB_12      -0.0942306000
_diffrn_orient_matrix_UB_13      -0.0564163000
_diffrn_orient_matrix_UB_21      0.0129878000
_diffrn_orient_matrix_UB_22      -0.1206707000
_diffrn_orient_matrix_UB_23      0.0441080000
_diffrn_orient_matrix_UB_31      -0.1731100000
_diffrn_orient_matrix_UB_32      0.0054411000
_diffrn_orient_matrix_UB_33      0.0018242000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22630
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.046
_diffrn_reflns_theta_min         2.054
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.126a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.312
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.007
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2695 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.39(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7157
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0612P)^2^+0.1261P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.844
_reflns_number_gt                6538
_reflns_number_total             7157
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce01159k2.cif
_cod_data_source_block           jds250003_fa_IV
_cod_depositor_comments
'Adding full bibliography for 7251450--7251455.cif.'
_cod_database_code               7251455
_chemical_oxdiff_formula         'C22 H22 N2 O4'
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.812
_diffrn_oxdiff_digest_frames
;
010e41379c47f69791521737a0a8acb0cf03568816c
;
_diffrn_oxdiff_digest_hkl
;
012a90aea3537fb6f85eba556444c145250b62
;
_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), C32(H32A,H32B), C43(H43A,H43B)
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), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29),
  C30(H30), C35(H35), C36(H36), C38(H38), C39(H39), C40(H40), C41(H41)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C22(H22A,H22B,H22C), C33(H33A,H33B,H33C), C44(H44A,H44B,
 H44C)
;
_shelx_res_checksum              2640
_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 1.856
_oxdiff_exptl_absorpt_empirical_full_min 0.622