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_7251450
_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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-21
_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                99.782(3)
_cell_angle_beta                 96.732(3)
_cell_angle_gamma                102.517(3)
_cell_formula_units_Z            1
_cell_length_a                   5.9187(2)
_cell_length_b                   8.0533(3)
_cell_length_c                   10.5862(3)
_cell_measurement_reflns_used    4199
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.1720
_cell_measurement_theta_min      4.2870
_cell_volume                     479.17(3)
_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 0.931
_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    -51.00 -11.00   0.50    0.05    --  -92.45  45.00-120.00   80
  2  \w    -51.00 -11.00   0.50    0.05    --  -92.45  45.00  30.00   80
  3  \w    -51.00 -11.00   0.50    0.05    --  -92.45  45.00 150.00   80
  4  \w    -26.00  35.00   0.50    0.05    --  -47.30  19.00  60.00  122
  5  \w     15.00 117.00   0.50    0.05    --   46.55  77.00  90.00  204
  6  \w     15.00 117.00   0.50    0.05    --   46.55  77.00   0.00  204
  7  \w     15.00  95.00   0.50    0.05    --   46.55  77.00-150.00  160
  8  \w     20.00 175.00   0.50    0.05    --   97.16   0.00-150.00  310
  9  \w     78.00 178.00   0.50    0.05    --  108.12 118.00 -78.00  200
 10  \w     51.00 115.00   0.50    0.05    --   46.55 161.00  72.00  128
 11  \w     50.00 157.00   0.50    0.05    --  108.12 161.00  72.00  214
 12  \w     31.00  71.00   0.50    0.05    --  108.12 -61.00  90.00   80
 13  \w     27.00 105.00   0.50    0.05    --   97.16 -77.00   0.00  156
 14  \w     27.00 105.00   0.50    0.05    --   97.16 -77.00   0.00  156
 15  \w     31.00  71.00   0.50    0.05    --  108.12 -61.00  60.00   80
 16  \w     31.00  71.00   0.50    0.05    --  108.12 -61.00   0.00   80
 17  \w     38.00 105.00   0.50    0.05    --  108.12 -77.00-150.00  134
 18  \w     16.00  51.00   0.50    0.05    --   97.16 -45.00-150.00   70
 19  \w     20.00  71.00   0.50    0.05    --   97.16 -61.00-180.00  102
 20  \w     22.00 109.00   0.50    0.05    --   97.16-118.00-165.00  174
 21  \w     35.00 105.00   0.50    0.05    --  108.12 -95.00   0.00  140
 22  \w     35.00 105.00   0.50    0.05    --  108.12 -95.00  90.00  140
 23  \w     35.00 105.00   0.50    0.05    --  108.12 -95.00  90.00  140
 24  \w   -130.00 -31.00   0.50    0.05    --  -47.30 161.00  72.00  198
 25  \w   -101.00  -8.00   0.50    0.05    --  -47.30 118.00 -78.00  186
 26  \w   -109.00 -17.00   0.50    0.05    --  -92.45 118.00 -78.00  184
 27  \w   -175.00 -23.00   0.50    0.05    --  -92.45 -15.00-150.00  304
 28  \w   -175.00 -23.00   0.50    0.05    --  -92.45 -15.00-150.00  304
 29  \w   -175.00 -23.00   0.50    0.05    --  -92.45 -15.00-150.00  304
 30  \w   -169.00 -67.00   0.50    0.05    --  -92.45 -61.00 -90.00  204
 31  \w   -167.00 -78.00   0.50    0.05    --  -92.45-118.00-165.00  178
 32  \w   -157.00 -49.00   0.50    0.05    --  -92.45-161.00  43.00  216
 33  \w   -115.00 -50.00   0.50    0.05    --  -47.30-161.00  43.00  130
;
_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      0.1222814000
_diffrn_orient_matrix_UB_12      -0.1226115000
_diffrn_orient_matrix_UB_13      -0.0792509000
_diffrn_orient_matrix_UB_21      -0.1597709000
_diffrn_orient_matrix_UB_22      0.0026642000
_diffrn_orient_matrix_UB_23      -0.1250996000
_diffrn_orient_matrix_UB_31      0.1802255000
_diffrn_orient_matrix_UB_32      0.1580536000
_diffrn_orient_matrix_UB_33      -0.0212260000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9088
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.316
_diffrn_reflns_theta_min         4.293
_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  0.952
_exptl_absorpt_correction_T_min  0.910
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       prism
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0059(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0552P)^2^+0.0945P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1660
_reflns_number_total             1892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce01159k2.cif
_cod_data_source_block           jds240053_fa_I
_cod_depositor_comments
'Adding full bibliography for 7251450--7251455.cif.'
_cod_database_code               7251450
_chemical_oxdiff_formula         'C11 H11 N1 O2'
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.860
_diffrn_oxdiff_digest_frames
;
01e65775425804872a1205c2c267543a450544228d3
;
_diffrn_oxdiff_digest_hkl
;
017fae741d46f35cc5d0235bb69082adb83ca5
;
_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              30034
_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 1.176
_oxdiff_exptl_absorpt_empirical_full_min 0.865