Supramolecular interactions and aromaticity in phenazine–hydroxybenzoic acid co-crystals
Wzgarda-Raj, Kinga; CrystEngComm 28 (2026) 1791–1800; doi:10.1039/D5CE01177A

data_7251512
_publ_section_title
;
 Supramolecular interactions and aromaticity in phenazine--hydroxybenzoic
 acid co-crystals
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1791
_journal_page_last               1800
_journal_paper_doi               10.1039/D5CE01177A
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         '4(C12 H8 N2), 3(C7 H6 O3)'
_chemical_formula_sum            'C69 H50 N8 O9'
_chemical_formula_weight         1135.17
_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   mixed
_audit_creation_date             2025-05-19
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-12-14 deposited with the CCDC.	2026-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                69.730(2)
_cell_angle_beta                 83.520(2)
_cell_angle_gamma                80.248(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6222(2)
_cell_length_b                   16.8759(4)
_cell_length_c                   20.4571(5)
_cell_measurement_reflns_used    17578
_cell_measurement_temperature    99.96(18)
_cell_measurement_theta_max      74.8130
_cell_measurement_theta_min      2.9650
_cell_volume                     2747.24(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.96(18)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.952
_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    -12.00  28.00   0.50    2.34    --  -47.24  19.00 -60.00   80
  2  \w    -86.00 -13.00   0.50    2.34    --  -47.24 125.00-180.00  146
  3  \w    -62.00  25.00   0.50    2.34    --  -47.24  57.00   0.00  174
  4  \w    -12.00  28.00   0.50    2.34    --  -47.24  19.00 -30.00   80
  5  \w    -12.00  28.00   0.50    2.34    --  -47.24  19.00 -90.00   80
  6  \w    -12.00  28.00   0.50    2.34    --  -47.24  19.00  90.00   80
  7  \w    -12.00  28.00   0.50    2.34    --  -47.24  19.00 120.00   80
  8  \w    -12.00  28.00   0.50    2.34    --  -47.24  19.00-120.00   80
  9  \w    -12.00  28.00   0.50    2.34    --  -47.24  19.00  30.00   80
 10  \w    -12.00  28.00   0.50    2.34    --  -47.24  19.00   0.00   80
 11  \w   -119.00 -92.00   0.50    2.34    --  -47.24 -57.00-120.00   54
 12  \w     34.00  93.00   0.50    2.34    --   47.24-125.00 150.00  118
 13  \w   -163.00 -78.00   0.50    9.37    --  -91.75 -50.00 -91.01  170
 14  \w    -49.00 -20.00   0.50    9.37    --  -91.75  45.00 -30.00   58
 15  \w   -114.00 -19.00   0.50    9.37    --  -91.75  77.00-180.00  190
 16  \w   -163.00 -92.00   0.50    9.37    --  -91.75 -57.00-141.03  142
 17  \w    -75.00 -19.00   0.50    9.37    --  -91.75  61.00  90.00  112
 18  \w   -114.00 -19.00   0.50    9.37    --  -91.75  77.00  90.00  190
 19  \w    -85.00 -22.00   0.50    9.37    --  -91.75 125.00 120.00  126
 20  \w   -163.00 -78.00   0.50    9.37    --  -91.75 -50.00 115.74  170
 21  \w   -163.00-103.00   0.50    9.37    --  -91.75 -95.00-150.00  120
 22  \w     36.00 111.00   0.50    9.37    --  105.58-125.00   0.00  150
 23  \w     33.00  75.00   0.50    9.37    --  105.58 -61.00 -60.00   84
 24  \w     33.00 105.00   0.50    9.37    --  105.58 -95.00 150.00  144
 25  \w     36.00 111.00   0.50    9.37    --  105.58-125.00  30.00  150
 26  \w     33.00 105.00   0.50    9.37    --  105.58 -95.00-150.00  144
 27  \w    104.00 178.00   0.50    9.37    --  105.58  77.00  30.00  148
 28  \w     93.00 178.00   0.50    9.37    --  105.58  47.00 -67.85  170
 29  \w     36.00 111.00   0.50    9.37    --  105.58-125.00-180.00  150
 30  \w     93.00 177.00   0.50    9.37    --  105.58  45.00  30.00  168
 31  \w     35.00 106.00   0.50    9.37    --  105.58 -97.00 177.00  142
 32  \w     33.00 105.00   0.50    9.37    --  105.58 -95.00  60.00  144
 33  \w     33.00 105.00   0.50    9.37    --  105.58 -95.00  30.00  144
 34  \w     35.00 107.00   0.50    9.37    --  105.58-105.00 -82.60  144
 35  \w   -119.00 -34.00   0.50    2.34    --  -47.24 -49.00 167.73  170
 36  \w   -119.00 -34.00   0.50    2.34    --  -47.24 -49.00  39.01  170
 37  \w   -119.00 -33.00   0.50    2.34    --  -47.24 -52.00-124.58  172
 38  \w   -119.00 -33.00   0.50    2.34    --  -47.24 -51.00 109.06  172
 39  \w   -119.00 -35.00   0.50    2.34    --  -47.24 -44.00 -25.61  168
 40  \w   -119.00 -34.00   0.50    2.34    --  -47.24 -50.00 -90.90  170
 41  \w   -119.00 -33.00   0.50    2.34    --  -47.24 -51.00 -46.31  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1139269000
_diffrn_orient_matrix_UB_12      0.0131628000
_diffrn_orient_matrix_UB_13      0.0469905000
_diffrn_orient_matrix_UB_21      -0.1305599000
_diffrn_orient_matrix_UB_22      -0.0097530000
_diffrn_orient_matrix_UB_23      0.0590899000
_diffrn_orient_matrix_UB_31      0.0543604000
_diffrn_orient_matrix_UB_32      -0.0969041000
_diffrn_orient_matrix_UB_33      0.0276969000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            52296
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.655
_diffrn_reflns_theta_min         2.819
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.78a (Rigaku Oxford Diffraction, 2020)
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            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     801
_refine_ls_number_reflns         10992
_refine_ls_number_restraints     785
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0702
_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^)+(0.1475P)^2^+0.1889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2002
_refine_ls_wR_factor_ref         0.2118
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8931
_reflns_number_total             10992
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce01177a2.cif
_cod_data_source_block           exp_1477
_cod_depositor_comments
'Adding full bibliography for 7251511--7251512.cif.'
_cod_original_cell_volume        2747.25(13)
_cod_database_code               7251512
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_cell_oxdiff_angle_alpha         69.731(2)
_cell_oxdiff_angle_beta          83.520(2)
_cell_oxdiff_angle_gamma         80.248(2)
_cell_oxdiff_length_a            8.6222(2)
_cell_oxdiff_length_b            16.8759(4)
_cell_oxdiff_length_c            20.4571(5)
_cell_oxdiff_measurement_reflns_used 17578
_cell_oxdiff_volume              2747.25(11)
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
4.a Aromatic/amide H refined with riding coordinates:
 C22C(H22C), C23C(H23C), C23B(H23B), C23A(H23A), C22B(H22B), C22A(H22A),
 C26A(H26A), C25C(H25C), C25A(H25A), C26C(H26C), C25B(H25B), C3D(H3D),
 C26B(H26B), C6D(H6D), C13A(H13A), C10D(H10D), C6B(H6B), C3A(H3A), C10A(H10A),
 C10B(H10B), C3B(H3B), C4D(H4D), C5D(H5D), C13D(H13D), C11A(H11A), C12A(H12A),
 C5B(H5B), C6A(H6A), C13B(H13B), C11D(H11D), C12D(H12D), C4B(H4B), C4A(H4A),
 C11B(H11B), C12B(H12B), C5A(H5A), C13C(H13C), C3C(H3C), C12C(H12C), C5C(H5C),
 C6C(H6C), C4C(H4C), C11C(H11C), C10C(H10C)
;
_shelx_res_checksum              19605
_shelx_hkl_checksum              15500
_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 1.171
_oxdiff_exptl_absorpt_empirical_full_min 0.884