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_7251451
_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_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           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-19
_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                 90.961(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.4185(5)
_cell_length_b                   9.8231(4)
_cell_length_c                   7.2136(3)
_cell_measurement_reflns_used    4045
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      72.6470
_cell_measurement_theta_min      3.2970
_cell_volume                     950.70(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.126a (Rigaku OD, 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 0.997
_diffrn_measured_fraction_theta_max 0.937
_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     26.00 127.00   0.50    1.10    --   46.05  46.00 109.00  202
  2  \w    -35.00  52.00   0.50    1.10    --   46.05 -46.00 -39.00  174
  3  \w   -127.00 -26.00   0.50    1.10    --  -46.92 -46.00 -39.00  202
  4  \w   -173.00 -72.00   0.50    4.40    --  -92.45 -46.00 -39.00  202
  5  \w   -173.00 -72.00   0.50    4.40    --  -92.45 -46.00 -39.00  202
  6  \w    -52.00 -12.00   0.50    4.40    --  -92.45  46.00 109.00   80
  7  \w     77.00 178.00   0.50    4.40    --   97.16  46.00 109.00  202
  8  \w     17.00  52.00   0.50    4.40    --   97.16 -46.00 -39.00   70
  9  \w     74.00 122.00   0.50    1.10    --   46.05 125.00 -30.00   96
 10  \w    -52.00  34.00   0.50    1.10    --  -46.92  46.00 109.00  172
 11  \w   -166.00 -83.00   0.50    4.40    --  -92.45 -95.00-120.00  166
 12  \w    -51.00 -11.00   0.50    4.40    --  -92.45  45.00 -90.00   80
 13  \w   -166.00 -83.00   0.50    4.40    --  -92.45 -95.00-120.00  166
 14  \w    -71.00 -15.00   0.50    4.40    --  -92.45  61.00 -90.00  112
 15  \w    -51.00 -11.00   0.50    4.40    --  -92.45  45.00 -30.00   80
 16  \w    -51.00 -11.00   0.50    4.40    --  -92.45  45.00  60.00   80
 17  \w    -51.00 -11.00   0.50    4.40    --  -92.45  45.00-120.00   80
 18  \w     16.00  51.00   0.50    4.40    --   97.16 -45.00 150.00   70
 19  \w     27.00 105.00   0.50    4.40    --   97.16 -77.00  60.00  156
 20  \w     35.00 105.00   0.50    4.40    --  108.12 -95.00   0.00  140
 21  \w     36.00  71.00   0.50    4.40    --  108.12 -61.00  90.00   70
 22  \w     42.00 102.00   0.50    4.40    --  108.12 -77.00-150.00  120
;
_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      -0.0727389000
_diffrn_orient_matrix_UB_12      0.0723939000
_diffrn_orient_matrix_UB_13      -0.1347320000
_diffrn_orient_matrix_UB_21      0.0888083000
_diffrn_orient_matrix_UB_22      0.0525494000
_diffrn_orient_matrix_UB_23      -0.1124397000
_diffrn_orient_matrix_UB_31      -0.0048472000
_diffrn_orient_matrix_UB_32      -0.1287628000
_diffrn_orient_matrix_UB_33      -0.1216320000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8654
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.437
_diffrn_reflns_theta_min         3.294
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.932
_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    1.322
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0474P)^2^+0.2826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1601
_reflns_number_total             1866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce01159k2.cif
_cod_data_source_block           jds240052_fa_III
_cod_depositor_comments
'Adding full bibliography for 7251450--7251455.cif.'
_cod_database_code               7251451
_chemical_oxdiff_formula         'C22 H24 N2 O4'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.903
_diffrn_oxdiff_digest_frames
;
01828faa26fb282caa983d35c4363654d902922d712
;
_diffrn_oxdiff_digest_hkl
;
019f813f56b11bb2bc668792eacae6f82c43dc
;
_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)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              57116
_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 1.389
_oxdiff_exptl_absorpt_empirical_full_min 0.712