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_7251454
_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         'C11 H11 N O4'
_chemical_formula_sum            'C11 H11 N O4'
_chemical_formula_weight         221.21
_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             2025-05-13
_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                69.905(5)
_cell_angle_beta                 72.221(5)
_cell_angle_gamma                68.201(5)
_cell_formula_units_Z            2
_cell_length_a                   6.9802(3)
_cell_length_b                   8.0029(4)
_cell_length_c                   10.9422(7)
_cell_measurement_reflns_used    5098
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.8160
_cell_measurement_theta_min      4.3910
_cell_volume                     521.80(5)
_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 0.931
_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     35.00 130.00   0.50    0.45    --  107.32-151.00 112.00  190
  2  \w     35.00 130.00   0.50    0.45    --  107.32-151.00 112.00  190
  3  \w     20.00 110.00   0.50    0.45    --   95.82-122.00 -86.00  180
  4  \w     20.00 110.00   0.50    0.45    --   95.82-122.00 -86.00  180
  5  \w     32.00 110.00   0.50    0.45    --  107.32-122.00 -86.00  156
  6  \w     81.00 112.00   0.50    0.45    --  107.32-125.00-180.00   62
  7  \w     32.00  63.00   0.50    0.45    --  107.32-125.00-180.00   62
  8  \w     11.00 103.00   0.50    0.11    --   46.11-122.00 -86.00  184
  9  \w    -36.00  26.00   0.50    0.11    --   46.11 -19.00 -90.00  124
 10  \w     25.00 105.00   0.50    0.45    --   95.82 -77.00  90.00  160
 11  \w     25.00 105.00   0.50    0.45    --   95.82 -77.00  90.00  160
 12  \w     33.00  64.00   0.50    0.45    --  107.32 -61.00  90.00   62
 13  \w     19.00  71.00   0.50    0.45    --   95.82 -61.00 -60.00  104
 14  \w     45.00 105.00   0.50    0.45    --  107.32 -77.00 -90.00  120
 15  \w     41.00 103.00   0.50    0.45    --  107.32 -77.00-180.00  124
 16  \w     15.00  51.00   0.50    0.45    --   95.82 -45.00-180.00   72
 17  \w     15.00  51.00   0.50    0.45    --   95.82 -45.00-120.00   72
 18  \w     15.00  51.00   0.50    0.45    --   95.82 -45.00 -90.00   72
 19  \w     15.00  51.00   0.50    0.45    --   95.82 -45.00 -30.00   72
 20  \w     15.00  51.00   0.50    0.45    --   95.82 -45.00 120.00   72
 21  \w     84.00 132.00   0.50    0.45    --  107.32 125.00-150.00   96
 22  \w    141.00 167.00   0.50    0.45    --  107.32 125.00-150.00   52
 23  \w     74.00 122.00   0.50    0.11    --   46.11 125.00 120.00   96
 24  \w     57.00 118.00   0.50    0.11    --   46.11 151.00 155.00  122
 25  \w     56.00 165.00   0.50    0.45    --   95.82 151.00 155.00  218
 26  \w   -110.00 -16.00   0.50    0.45    --  -92.22 122.00  -5.00  188
 27  \w   -130.00 -26.00   0.50    0.45    --  -92.22 151.00 155.00  208
 28  \w   -124.00 -26.00   0.50    0.11    --  -47.36 151.00 155.00  196
 29  \w   -104.00 -11.00   0.50    0.11    --  -47.36 122.00  -5.00  186
 30  \w    -51.00 -11.00   0.50    0.45    --  -92.22  45.00  30.00   80
 31  \w    -35.00  -9.00   0.50    0.45    --  -92.22  30.00 150.00   52
 32  \w    -51.00 -11.00   0.50    0.45    --  -92.22  45.00 -60.00   80
 33  \w    -51.00 -11.00   0.50    0.45    --  -92.22  45.00-180.00   80
 34  \w    -35.00  -9.00   0.50    0.45    --  -92.22  30.00-150.00   52
 35  \w    -35.00  -9.00   0.50    0.45    --  -92.22  30.00-120.00   52
 36  \w    -26.00  35.00   0.50    0.11    --  -47.36  19.00-120.00  122
 37  \w    -35.00  -9.00   0.50    0.45    --  -92.22  30.00 120.00   52
 38  \w    -26.00  35.00   0.50    0.11    --  -47.36  19.00 120.00  122
 39  \w   -119.00 -56.00   0.50    0.11    --  -47.36-151.00 112.00  126
 40  \w   -165.00 -55.00   0.50    0.45    --  -92.22-151.00 112.00  220
 41  \w   -168.00 -75.00   0.50    0.45    --  -92.22-122.00 -86.00  186
 42  \w   -169.00 -67.00   0.50    0.45    --  -92.22 -61.00-180.00  204
 43  \w   -169.00 -67.00   0.50    0.45    --  -92.22 -61.00-180.00  204
;
_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      -0.0158259000
_diffrn_orient_matrix_UB_12      -0.0787785000
_diffrn_orient_matrix_UB_13      -0.1055421000
_diffrn_orient_matrix_UB_21      -0.0504818000
_diffrn_orient_matrix_UB_22      -0.1688254000
_diffrn_orient_matrix_UB_23      0.1098462000
_diffrn_orient_matrix_UB_31      -0.2369645000
_diffrn_orient_matrix_UB_32      0.1067795000
_diffrn_orient_matrix_UB_33      0.0156322000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9705
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.104
_diffrn_reflns_theta_min         4.395
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.907
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       plate
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0627P)^2^+0.0859P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1139
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1790
_reflns_number_total             2050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce01159k2.cif
_cod_data_source_block           jds250024_fa_SM2
_cod_depositor_comments
'Adding full bibliography for 7251450--7251455.cif.'
_cod_database_code               7251454
_chemical_oxdiff_formula         'C11 H11 N1 O4'
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.875
_diffrn_oxdiff_digest_frames
;
0171bd6a42202ab6afe001247ed0c929fa0541284cf
;
_diffrn_oxdiff_digest_hkl
;
01d665dfaac8a1930dec29c507afef54d4ac95
;
_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              84696
_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 1.962
_oxdiff_exptl_absorpt_empirical_full_min 0.699