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

data_7251825
_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, C9 H11 N3 O3'
_chemical_formula_sum            'C18 H22 N4 O5'
_chemical_formula_weight         374.39
_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             2023-02-04
_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                79.345(2)
_cell_angle_beta                 78.280(3)
_cell_angle_gamma                80.4467(17)
_cell_formula_units_Z            2
_cell_length_a                   6.21761(15)
_cell_length_b                   12.5048(2)
_cell_length_c                   12.7578(4)
_cell_measurement_reflns_used    11948
_cell_measurement_temperature    200.0(1)
_cell_measurement_theta_max      79.4880
_cell_measurement_theta_min      3.6100
_cell_volume                     945.96(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_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      200.0(1)
_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 0.985
_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   -116.00 -74.00   0.50    2.00    --  -49.82-128.00 140.00   84
  2  \w    -89.00 -63.00   0.50    2.00    --  -49.82 142.00  25.00   52
  3  \w    -86.00 -60.00   0.50    2.00    --  -49.82 128.00-145.00   52
  4  \w   -111.00 -86.00   0.50    2.00    --  -49.82-142.00 -31.00   50
  5  \w     53.00 100.00   0.50    2.00    --   49.82-142.00 -31.00   94
  6  \w     37.00  96.00   0.50    2.00    --   49.82-128.00 140.00  118
  7  \w   -133.00-108.00   0.50    9.00    --  -90.00-142.00 -31.00   50
  8  \w   -135.00-110.00   0.50    9.00    --  -90.00-128.00 140.00   50
  9  \w    -84.00 -59.00   0.50    9.00    --  -90.00 142.00  25.00   50
 10  \w    -78.00 -53.00   0.50    9.00    --  -90.00 128.00-145.00   50
 11  \w    104.00 129.00   0.50    9.00    --  111.50 142.00  25.00   50
 12  \w     92.00 124.00   0.50    9.00    --  111.50-142.00 -31.00   64
 13  \w    122.00 149.00   0.50    9.00    --  111.50 128.00-145.00   54
 14  \w     71.00  96.00   0.50    9.00    --  111.50-128.00 140.00   50
 15  \w   -119.00 -31.00   0.50    2.00    --  -49.82 -77.00 120.00  176
 16  \w     -5.00  20.00   0.50    2.00    --  -49.82  19.00-120.00   50
 17  \w   -114.00 -73.00   0.50    2.00    --  -49.82-125.00 -60.00   82
 18  \w     29.00 119.00   0.50    2.00    --   49.82  77.00-150.00  180
 19  \w   -161.00 -90.00   0.50    9.00    --  -90.00 -15.00   0.00  142
 20  \w    -51.00 -26.00   0.50    9.00    --  -90.00  45.00-180.00   50
 21  \w    -46.00 -19.00   0.50    9.00    --  -90.00  45.00 150.00   54
 22  \w     46.00  91.00   0.50    9.00    --  111.50-125.00  90.00   90
 23  \w    142.00 178.00   0.50    9.00    --  111.50  45.00-150.00   72
 24  \w     41.00  66.00   0.50    9.00    --  111.50 -61.00 120.00   50
 25  \w    122.00 153.00   0.50    9.00    --  111.50 125.00   0.00   62
 26  \w    106.00 132.00   0.50    9.00    --  111.50  15.00-180.00   52
 27  \w     77.00 110.00   0.50    9.00    --  111.50-125.00  60.00   66
 28  \w     93.00 119.00   0.50    9.00    --  111.50  77.00 -90.00   52
 29  \w     77.00 111.00   0.50    9.00    --  111.50-125.00-180.00   68
 30  \w     80.00 108.00   0.50    9.00    --  111.50-125.00 120.00   56
 31  \w    111.00 159.00   0.50    9.00    --  111.50  30.00   0.00   96
 32  \w     82.00 111.00   0.50    9.00    --  111.50-125.00-150.00   58
 33  \w    144.00 170.00   0.50    9.00    --  111.50  61.00 120.00   52
 34  \w    112.00 175.00   0.50    9.00    --  111.50  77.00   0.00  126
 35  \w     50.00 101.00   0.50    9.00    --  111.50 -94.00 -90.00  102
 36  \w     48.00 102.00   0.50    9.00    --  111.50 -77.00 150.00  108
 37  \w     44.00 102.00   0.50    9.00    --  111.50-125.00   0.00  116
 38  \w    107.00 162.00   0.50    9.00    --  111.50  15.00-150.00  110
 39  \w     99.00 124.00   0.50    9.00    --  111.50 125.00 -60.00   50
 40  \w    138.00 164.00   0.50    9.00    --  111.50 125.00 -60.00   52
 41  \w     63.00  88.00   0.50    9.00    --  111.50 -77.00-150.00   50
 42  \w     52.00  96.00   0.50    9.00    --  111.50 -94.00  60.00   88
 43  \w     85.00 110.00   0.50    9.00    --  111.50 -79.00   0.93   50
 44  \w    125.00 177.00   0.50    9.00    --  111.50  77.00 -90.00  104
 45  \w     41.00  70.00   0.50    9.00    --  111.50 -61.00-120.00   58
 46  \w     41.00  66.00   0.50    9.00    --  111.50 -61.00  90.00   50
 47  \w     86.00 111.00   0.50    9.00    --  111.50-125.00-120.00   50
 48  \w     41.00  67.00   0.50    9.00    --  111.50 -61.00  60.00   52
 49  \w    106.00 176.00   0.50    9.00    --  111.50  30.00 -90.00  140
 50  \w     44.00  73.00   0.50    9.00    --  111.50-137.00-132.34   58
 51  \w     96.00 121.00   0.50    9.00    --  111.50-137.00-132.34   50
 52  \w    107.00 133.00   0.50    9.00    --  111.50  61.00 120.00   52
 53  \w     44.00 105.00   0.50    9.00    --  111.50-125.00  30.00  122
 54  \w    133.00 178.00   0.50    9.00    --  111.50 125.00 -30.00   90
 55  \w    100.00 126.00   0.50    9.00    --  111.50  77.00-180.00   52
 56  \w    152.00 178.00   0.50    9.00    --  111.50  77.00-180.00   52
 57  \w     84.00 109.00   0.50    9.00    --  111.50 -83.00 -46.94   50
 58  \w    130.00 170.00   0.50    9.00    --  111.50 125.00-180.00   80
 59  \w     51.00  76.00   0.50    9.00    --  111.50 -77.00-120.00   50
 60  \w     69.00  95.00   0.50    9.00    --  111.50 -77.00 -90.00   52
 61  \w     43.00 105.00   0.50    9.00    --  111.50-125.00 150.00  124
 62  \w    125.00 151.00   0.50    9.00    --  111.50  30.00  90.00   52
 63  \w    116.00 142.00   0.50    9.00    --  111.50 125.00-150.00   52
 64  \w    130.00 177.00   0.50    9.00    --  111.50 125.00-120.00   94
 65  \w    110.00 135.00   0.50    9.00    --  111.50 125.00  90.00   50
 66  \w    150.00 175.00   0.50    9.00    --  111.50 125.00  90.00   50
 67  \w    118.00 143.00   0.50    9.00    --  111.50 125.00 150.00   50
 68  \w     92.00 153.00   0.50    9.00    --  111.50  77.00 -60.00  122
 69  \w    104.00 131.00   0.50    9.00    --  111.50  77.00  60.00   54
 70  \w    103.00 139.00   0.50    9.00    --  111.50  77.00 120.00   72
 71  \w    107.00 133.00   0.50    9.00    --  111.50  77.00 150.00   52
 72  \w     44.00  70.00   0.50    9.00    --  111.50 -79.00   0.93   52
 73  \w     79.00 104.00   0.50    9.00    --  111.50 -94.00-150.00   50
 74  \w     50.00  77.00   0.50    9.00    --  111.50 -86.00 -52.04   54
 75  \w     90.00 128.00   0.50    9.00    --  111.50 -86.00 -52.04   76
 76  \w    107.00 132.00   0.50    9.00    --  111.50 -88.00-122.12   50
 77  \w     43.00  69.00   0.50    9.00    --  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      0.0550673000
_diffrn_orient_matrix_UB_12      0.0249981000
_diffrn_orient_matrix_UB_13      -0.1246221000
_diffrn_orient_matrix_UB_21      0.2488867000
_diffrn_orient_matrix_UB_22      -0.0155489000
_diffrn_orient_matrix_UB_23      0.0051280000
_diffrn_orient_matrix_UB_31      0.0147659000
_diffrn_orient_matrix_UB_32      -0.1230173000
_diffrn_orient_matrix_UB_33      -0.0058687000
_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  0.0236
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17956
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.089
_diffrn_reflns_theta_min         3.582
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
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    1.314
_exptl_crystal_F_000             396
_exptl_crystal_recrystallization_method 'crystallized from methanol'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0591P)^2^+0.1357P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3741
_reflns_number_total             4064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ce00063k2.cif
_cod_data_source_block           exp_650_auto
_cod_depositor_comments
'Adding full bibliography for 7251818--7251826.cif.'
_cod_database_code               7251825
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C18H22N4O5
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.775
_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)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C15(H15), C16(H16), C18(H18)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              42144
_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 0.612