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

data_7251823
_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         'C7 H7 N O2, C10 H13 N3 O3'
_chemical_formula_sum            'C17 H20 N4 O5'
_chemical_formula_weight         360.37
_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     direct
_audit_creation_date             2023-10-26
_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                73.875(3)
_cell_angle_beta                 79.965(2)
_cell_angle_gamma                76.405(2)
_cell_formula_units_Z            2
_cell_length_a                   6.15171(12)
_cell_length_b                   12.3495(4)
_cell_length_c                   12.6749(4)
_cell_measurement_reflns_used    8885
_cell_measurement_temperature    295.9(3)
_cell_measurement_theta_max      79.5070
_cell_measurement_theta_min      3.6520
_cell_volume                     892.97(5)
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_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    -38.00  25.00   0.50    3.00    --  -47.98  33.00  52.00  126
  2  \w    -85.00 -36.00   0.50    3.00    --  -47.98 -33.00-105.00   98
  3  \w   -118.00 -88.00   0.50    3.00    --  -47.98 -33.00-105.00   60
  4  \w    -71.00 -24.00   0.50    3.00    --  -47.98  77.00-120.00   94
  5  \w    -20.00  28.00   0.50    3.00    --  -47.98  19.00 -30.00   96
  6  \w     -5.00  20.00   0.50    3.00    --  -47.98  77.00-120.00   50
  7  \w    -26.00  10.00   0.50    3.00    --   47.98 -19.00 120.00   72
  8  \w     51.00 116.00   0.50    3.00    --   47.98  33.00  52.00  130
  9  \w    -23.00  37.00   0.50    3.00    --   47.98 -33.00-105.00  120
 10  \w     37.00  93.00   0.50    3.00    --   47.98-125.00   0.00  112
 11  \w   -130.00 -95.00   0.50   12.00    --  -91.75 -33.00-105.00   70
 12  \w    -76.00 -29.00   0.50   12.00    --  -91.75 125.00  90.00   94
 13  \w    139.00 170.00   0.50   12.00    --  113.25  33.00  52.00   62
 14  \w    103.00 129.00   0.50   12.00    --  113.25  33.00  52.00   52
 15  \w     46.00 102.00   0.50   12.00    --  113.25 -94.00 -60.00  112
 16  \w    101.00 173.00   0.50   12.00    --  113.25  30.00-180.00  144
 17  \w    111.00 155.00   0.50   12.00    --  113.25   0.00-150.00   88
 18  \w     70.00  96.00   0.50   12.00    --  113.25 -94.00 120.00   52
 19  \w     85.00 111.00   0.50   12.00    --  113.25-125.00  30.00   52
 20  \w     79.00 104.00   0.50   12.00    --  113.25 -94.00 -90.00   50
 21  \w     45.00  70.00   0.50   12.00    --  113.25 -61.00 150.00   50
 22  \w     43.00  70.00   0.50   12.00    --  113.25 -61.00 -60.00   54
 23  \w     74.00 104.00   0.50   12.00    --  113.25 -77.00   0.00   60
 24  \w     42.00  71.00   0.50   12.00    --  113.25 -61.00-180.00   58
 25  \w     42.00  69.00   0.50   12.00    --  113.25 -61.00 -30.00   54
 26  \w     66.00 107.00   0.50   12.00    --  113.25-104.00 155.29   82
 27  \w     42.00  96.00   0.50   12.00    --  113.25 -77.00-120.00  108
 28  \w     45.00  74.00   0.50   12.00    --  113.25 -77.00-180.00   58
 29  \w     45.00  71.00   0.50   12.00    --  113.25 -77.00  30.00   52
 30  \w     72.00 109.00   0.50   12.00    --  113.25-125.00 150.00   74
 31  \w    109.00 177.00   0.50   12.00    --  113.25  30.00-120.00  136
 32  \w     78.00 111.00   0.50   12.00    --  113.25-125.00 -60.00   66
 33  \w     54.00 106.00   0.50   12.00    --  113.25 -94.00-180.00  104
 34  \w     42.00  76.00   0.50   12.00    --  113.25 -94.00 -90.00   68
 35  \w    124.00 150.00   0.50   12.00    --  113.25 125.00-150.00   52
 36  \w     70.00  96.00   0.50   12.00    --  113.25 -94.00-150.00   52
 37  \w     43.00  70.00   0.50   12.00    --  113.25 -77.00   0.00   54
 38  \w    142.00 176.00   0.50   12.00    --  113.25  30.00-150.00   68
 39  \w     79.00 104.00   0.50   12.00    --  113.25 -94.00  30.00   50
 40  \w     49.00  79.00   0.50   12.00    --  113.25 -77.00 -60.00   60
 41  \w    103.00 175.00   0.50   12.00    --  113.25  45.00 120.00  144
 42  \w    116.00 141.00   0.50   12.00    --  113.25  30.00-150.00   50
 43  \w     95.00 129.00   0.50   12.00    --  113.25 125.00 -90.00   68
 44  \w    133.00 164.00   0.50   12.00    --  113.25 125.00 -90.00   62
 45  \w    101.00 126.00   0.50   12.00    --  113.25  77.00 150.00   50
 46  \w     46.00  71.00   0.50   12.00    --  113.25 -94.00 150.00   50
 47  \w     78.00 105.00   0.50   12.00    --  113.25 -94.00 150.00   54
 48  \w     64.00  90.00   0.50   12.00    --  113.25 -86.00 -76.10   52
 49  \w     99.00 124.00   0.50   12.00    --  113.25 -86.00 -76.10   50
 50  \w    101.00 154.00   0.50   12.00    --  113.25  45.00 -60.00  106
 51  \w     46.00 111.00   0.50   12.00    --  113.25-125.00 120.00  130
 52  \w     79.00 104.00   0.50   12.00    --  113.25 -77.00-150.00   50
 53  \w    107.00 137.00   0.50   12.00    --  113.25 -79.00  58.70   60
 54  \w     81.00 106.00   0.50   12.00    --  113.25 -94.00 -30.00   50
 55  \w     52.00  78.00   0.50   12.00    --  113.25 -94.00   0.00   52
 56  \w     81.00 106.00   0.50   12.00    --  113.25 -94.00   0.00   50
 57  \w     72.00 106.00   0.50   12.00    --  113.25 -94.00  90.00   68
 58  \w     83.00 108.00   0.50   12.00    --  113.25-108.00 -83.67   50
 59  \w     44.00  74.00   0.50   12.00    --  113.25-125.00  90.00   60
 60  \w    131.00 157.00   0.50   12.00    --  113.25  45.00   0.00   52
 61  \w    113.00 173.00   0.50   12.00    --  113.25  30.00  90.00  120
 62  \w    115.00 140.00   0.50   12.00    --  113.25  30.00 120.00   50
 63  \w    120.00 159.00   0.50   12.00    --  113.25  61.00 -30.00   78
 64  \w    100.00 126.00   0.50   12.00    --  113.25  61.00  30.00   52
 65  \w     74.00 107.00   0.50   12.00    --  113.25-106.00  83.85   66
 66  \w    101.00 126.00   0.50   12.00    --  113.25  77.00  30.00   50
 67  \w    135.00 177.00   0.50   12.00    --  113.25  77.00  90.00   84
 68  \w     46.00  72.00   0.50   12.00    --  113.25 -79.00  58.70   52
 69  \w     42.00  68.00   0.50   12.00    --  113.25 -94.00  30.00   52
 70  \w     60.00 111.00   0.50   12.00    --  113.25-125.00 -90.00  102
;
_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      0.0680136000
_diffrn_orient_matrix_UB_12      -0.1305299000
_diffrn_orient_matrix_UB_13      0.0485166000
_diffrn_orient_matrix_UB_21      -0.2252990000
_diffrn_orient_matrix_UB_22      -0.0166714000
_diffrn_orient_matrix_UB_23      -0.0241017000
_diffrn_orient_matrix_UB_31      0.1091667000
_diffrn_orient_matrix_UB_32      -0.0152430000
_diffrn_orient_matrix_UB_33      -0.1152915000
_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  0.0174
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14844
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.078
_diffrn_reflns_theta_min         3.655
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72756
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_recrystallization_method 'crystallized from methanol'
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3854
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0744P)^2^+0.0660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1287
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3482
_reflns_number_total             3854
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ce00063k2.cif
_cod_data_source_block           exp_787_auto
_cod_depositor_comments
'Adding full bibliography for 7251818--7251826.cif.'
_cod_original_cell_volume        892.97(4)
_cod_database_code               7251823
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C17H20N4O5
_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. Rigid bond restraints
 O25, N24
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
3.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C6(H6), C14(H14), C2(H2), C5(H5), C3(H3)
3.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              36531
_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 1.670
_oxdiff_exptl_absorpt_empirical_full_min 0.735