Modulating some photophysical properties of cocrystals
Marasinghe, Aloka A.; Averkiev, Boris B.; Aakeröy, Christer B.; CrystEngComm  (2026) –; doi:10.1039/D6CE00063K

data_7251822
_publ_section_title
;
 Modulating some photophysical properties of cocrystals
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2548
_journal_page_last               2559
_journal_paper_doi               10.1039/D6CE00063K
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C9 H11 N O2, C11 H15 N3 O3'
_chemical_formula_sum            'C20 H26 N4 O5'
_chemical_formula_weight         402.45
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-12
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2025-12-21 deposited with the CCDC.	2026-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                76.6124(10)
_cell_angle_beta                 75.8298(12)
_cell_angle_gamma                80.7872(10)
_cell_formula_units_Z            2
_cell_length_a                   6.42159(9)
_cell_length_b                   12.65205(14)
_cell_length_c                   13.02701(17)
_cell_measurement_reflns_used    15178
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      79.5850
_cell_measurement_theta_min      3.5690
_cell_volume                     992.29(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.984
_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    -84.00 -10.00   0.50    0.80    --  -49.82 121.00-134.00  148
  2  \w   -105.00 -27.00   0.50    0.80    --  -49.82 152.00  25.00  156
  3  \w   -121.00 -55.00   0.50    0.80    --  -49.82-152.00 -16.00  132
  4  \w     32.00  91.00   0.50    0.80    --   49.82-121.00 143.00  118
  5  \w     48.00 112.00   0.50    0.80    --   49.82-152.00 -16.00  128
  6  \w    -84.00 -21.00   0.50    3.50    --  -90.00 121.00-134.00  126
  7  \w   -105.00 -27.00   0.50    3.50    --  -90.00 152.00  25.00  156
  8  \w   -159.00 -76.00   0.50    3.50    --  -90.00-121.00 143.00  166
  9  \w   -148.00 -55.00   0.50    3.50    --  -90.00-152.00 -16.00  186
 10  \w     77.00 164.00   0.50    3.50    --  111.50 152.00  25.00  174
 11  \w     98.00 178.00   0.50    3.50    --  111.50 121.00-134.00  160
 12  \w    100.00 131.00   0.50    3.50    --  111.50-152.00 -16.00   62
 13  \w     52.00  77.00   0.50    3.50    --  111.50-121.00 143.00   50
 14  \w   -117.00 -77.00   0.50    0.80    --  -49.82-125.00-150.00   80
 15  \w    -24.00  23.00   0.50    0.80    --  -49.82  19.00-120.00   94
 16  \w    -23.00  16.00   0.50    0.80    --  -49.82  19.00 150.00   78
 17  \w   -119.00 -31.00   0.50    0.80    --  -49.82 -77.00-180.00  176
 18  \w    -40.00  21.00   0.50    0.80    --  -49.82  38.00 120.00  122
 19  \w   -160.00 -86.00   0.50    3.50    --  -90.00 -45.00-150.00  148
 20  \w    150.00 178.00   0.50    3.50    --  111.50  45.00-150.00   56
 21  \w    107.00 136.00   0.50    3.50    --  111.50  45.00-150.00   58
 22  \w    104.00 130.00   0.50    3.50    --  111.50  30.00 -30.00   52
 23  \w    130.00 169.00   0.50    3.50    --  111.50  15.00 150.00   78
 24  \w     44.00  69.00   0.50    3.50    --  111.50-125.00  60.00   50
 25  \w     85.00 110.00   0.50    3.50    --  111.50-125.00  60.00   50
 26  \w     92.00 117.00   0.50    3.50    --  111.50  77.00  30.00   50
 27  \w    153.00 178.00   0.50    3.50    --  111.50  77.00  30.00   50
 28  \w     48.00  82.00   0.50    3.50    --  111.50 -77.00-150.00   68
 29  \w     79.00 108.00   0.50    3.50    --  111.50-108.00  -6.10   58
 30  \w     79.00 111.00   0.50    3.50    --  111.50-125.00-150.00   64
 31  \w     53.00  78.00   0.50    3.50    --  111.50-125.00-150.00   50
 32  \w     49.00  97.00   0.50    3.50    --  111.50 -94.00  90.00   96
 33  \w     43.00  77.00   0.50    3.50    --  111.50-125.00   0.00   68
 34  \w     49.00  96.00   0.50    3.50    --  111.50 -77.00   0.00   94
 35  \w    118.00 173.00   0.50    3.50    --  111.50  15.00-150.00  110
 36  \w    102.00 155.00   0.50    3.50    --  111.50  45.00 -60.00  106
 37  \w    118.00 178.00   0.50    3.50    --  111.50  45.00-120.00  120
 38  \w     80.00 111.00   0.50    3.50    --  111.50-125.00-120.00   62
 39  \w     71.00 107.00   0.50    3.50    --  111.50-103.00 119.42   72
 40  \w     47.00  77.00   0.50    3.50    --  111.50 -82.00  -6.77   60
 41  \w     94.00 120.00   0.50    3.50    --  111.50 -82.00  -6.77   52
 42  \w    131.00 172.00   0.50    3.50    --  111.50  45.00 150.00   82
 43  \w     80.00 105.00   0.50    3.50    --  111.50 -77.00 120.00   50
 44  \w    107.00 163.00   0.50    3.50    --  111.50  30.00  90.00  112
 45  \w     43.00  70.00   0.50    3.50    --  111.50-125.00  90.00   54
 46  \w     43.00 102.00   0.50    3.50    --  111.50-125.00 -90.00  118
 47  \w     78.00 110.00   0.50    3.50    --  111.50-125.00 120.00   64
 48  \w     65.00 105.00   0.50    3.50    --  111.50 -94.00 -30.00   80
 49  \w    125.00 157.00   0.50    3.50    --  111.50  30.00-150.00   64
 50  \w     53.00  96.00   0.50    3.50    --  111.50 -77.00 150.00   86
 51  \w     51.00 103.00   0.50    3.50    --  111.50 -94.00 -60.00  104
 52  \w     41.00  76.00   0.50    3.50    --  111.50 -77.00 120.00   70
 53  \w     42.00  68.00   0.50    3.50    --  111.50 -94.00 120.00   52
 54  \w     78.00 104.00   0.50    3.50    --  111.50 -94.00 120.00   52
 55  \w     73.00 110.00   0.50    3.50    --  111.50-121.00 126.06   74
 56  \w    113.00 142.00   0.50    3.50    --  111.50  30.00 120.00   58
 57  \w    145.00 170.00   0.50    3.50    --  111.50  30.00 120.00   50
 58  \w    136.00 174.00   0.50    3.50    --  111.50  30.00 -30.00   76
 59  \w    101.00 139.00   0.50    3.50    --  111.50  61.00 150.00   76
 60  \w     43.00  87.00   0.50    3.50    --  111.50 -77.00-180.00   88
 61  \w     51.00  77.00   0.50    3.50    --  111.50 -77.00 -60.00   52
 62  \w     43.00  92.00   0.50    3.50    --  111.50 -77.00  30.00   98
 63  \w     44.00 104.00   0.50    3.50    --  111.50 -94.00 -90.00  120
 64  \w     42.00  68.00   0.50    3.50    --  111.50 -94.00 150.00   52
 65  \w     72.00  98.00   0.50    3.50    --  111.50 -94.00 150.00   52
 66  \w     70.00  95.00   0.50    3.50    --  111.50-125.00 -60.00   50
 67  \w    118.00 157.00   0.50    3.50    --  111.50  30.00  30.00   78
 68  \w    108.00 134.00   0.50    3.50    --  111.50  61.00 -30.00   52
 69  \w    124.00 174.00   0.50    3.50    --  111.50 125.00   0.00  100
 70  \w     93.00 138.00   0.50    3.50    --  111.50  77.00 -30.00   90
 71  \w     99.00 133.00   0.50    3.50    --  111.50 -82.00-177.03   68
 72  \w     88.00 114.00   0.50    3.50    --  111.50 -88.00 -19.07   52
 73  \w     42.00  68.00   0.50    3.50    --  111.50 -61.00   0.00   52
;
_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      0.0799782000
_diffrn_orient_matrix_UB_12      0.0133570000
_diffrn_orient_matrix_UB_13      -0.1233754000
_diffrn_orient_matrix_UB_21      -0.2261185000
_diffrn_orient_matrix_UB_22      -0.0166097000
_diffrn_orient_matrix_UB_23      -0.0100313000
_diffrn_orient_matrix_UB_31      -0.0665760000
_diffrn_orient_matrix_UB_32      0.1241135000
_diffrn_orient_matrix_UB_33      -0.0134522000
_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  0.0187
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20759
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.934
_diffrn_reflns_theta_min         3.572
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_recrystallization_method 'crystallized from methanol'
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0655P)^2^+0.1845P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1156
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3980
_reflns_number_total             4253
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ce00063k2.cif
_cod_data_source_block           exp_781_auto
_cod_depositor_comments
'Adding full bibliography for 7251818--7251826.cif.'
_cod_database_code               7251822
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C7H5O4N2
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.878
_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:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C14(H14), C15(H15), C17(H17)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              77818
_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 1.274
_oxdiff_exptl_absorpt_empirical_full_min 0.790