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

data_7251824
_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 N3 O3, C7 H7 N O2'
_chemical_formula_sum            'C16 H18 N4 O5'
_chemical_formula_weight         346.34
_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             2023-02-05
_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                73.991(9)
_cell_angle_beta                 78.882(9)
_cell_angle_gamma                78.277(7)
_cell_formula_units_Z            2
_cell_length_a                   5.8059(4)
_cell_length_b                   11.8005(10)
_cell_length_c                   12.9057(16)
_cell_measurement_reflns_used    6508
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      79.8590
_cell_measurement_theta_min      3.5960
_cell_volume                     823.35(14)
_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      200.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.934
_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    -51.00 -21.00   0.50    0.80    --  -49.44 122.00 -58.00   60
  2  \w    -96.00 -59.00   0.50    0.80    --  -49.44-151.00  58.00   74
  3  \w    -74.00 -48.00   0.50    0.80    --  -49.44 151.00 102.00   52
  4  \w     53.00 111.00   0.50    0.80    --   49.44-151.00  58.00  116
  5  \w     51.00  90.00   0.50    0.80    --   49.44-122.00-140.00   78
  6  \w   -141.00-116.00   0.50    3.50    --  -90.00-122.00-140.00   50
  7  \w   -102.00 -77.00   0.50    3.50    --  -90.00-151.00  58.00   50
  8  \w    -77.00 -52.00   0.50    3.50    --  -90.00 122.00 -58.00   50
  9  \w    -89.00 -64.00   0.50    3.50    --  -90.00 151.00 102.00   50
 10  \w     63.00  90.00   0.50    3.50    --  111.50-151.00  58.00   54
 11  \w     53.00  80.00   0.50    3.50    --  111.50-122.00-140.00   54
 12  \w    113.00 138.00   0.50    3.50    --  111.50 122.00 -58.00   50
 13  \w    131.00 156.00   0.50    3.50    --  111.50 151.00 102.00   50
 14  \w   -112.00 -87.00   0.50    0.80    --  -49.44-125.00   0.00   50
 15  \w    -15.00  23.00   0.50    0.80    --  -49.44  19.00-120.00   76
 16  \w    -11.00  17.00   0.50    0.80    --  -49.44  19.00  60.00   56
 17  \w    -26.00  19.00   0.50    0.80    --  -49.44  19.00-150.00   90
 18  \w    -25.00   9.00   0.50    0.80    --  -49.44  19.00-180.00   68
 19  \w    -18.00  22.00   0.50    0.80    --   49.44 -19.00 150.00   80
 20  \w    -23.00  20.00   0.50    0.80    --   49.44 -19.00-150.00   86
 21  \w    -50.00 -22.00   0.50    3.50    --  -90.00  45.00   0.00   56
 22  \w    -50.00 -25.00   0.50    3.50    --  -90.00  45.00  90.00   50
 23  \w   -154.00 -82.00   0.50    3.50    --  -90.00 -30.00 -90.00  144
 24  \w     43.00  87.00   0.50    3.50    --  111.50 -94.00  60.00   88
 25  \w    104.00 166.00   0.50    3.50    --  111.50  30.00-180.00  124
 26  \w     47.00 110.00   0.50    3.50    --  111.50-125.00-180.00  126
 27  \w     42.00 104.00   0.50    3.50    --  111.50 -77.00   0.00  124
 28  \w     42.00  68.00   0.50    3.50    --  111.50 -61.00 -60.00   52
 29  \w    144.00 177.00   0.50    3.50    --  111.50  15.00 -60.00   66
 30  \w    114.00 169.00   0.50    3.50    --  111.50  15.00 120.00  110
 31  \w    103.00 166.00   0.50    3.50    --  111.50  45.00 -30.00  126
 32  \w     44.00 104.00   0.50    3.50    --  111.50 -94.00-120.00  120
 33  \w     43.00  71.00   0.50    3.50    --  111.50 -61.00-180.00   56
 34  \w     70.00 107.00   0.50    3.50    --  111.50-104.00-150.84   74
 35  \w    105.00 135.00   0.50    3.50    --  111.50  15.00 -60.00   60
 36  \w     46.00  93.00   0.50    3.50    --  111.50 -77.00-120.00   94
 37  \w    141.00 166.00   0.50    3.50    --  111.50  30.00   0.00   50
 38  \w    103.00 159.00   0.50    3.50    --  111.50  45.00  30.00  112
 39  \w     73.00 100.00   0.50    3.50    --  111.50 -94.00  90.00   54
 40  \w     44.00  71.00   0.50    3.50    --  111.50-125.00  30.00   54
 41  \w     85.00 110.00   0.50    3.50    --  111.50-125.00  30.00   50
 42  \w     48.00 101.00   0.50    3.50    --  111.50 -94.00 -60.00  106
 43  \w    117.00 155.00   0.50    3.50    --  111.50  15.00 -90.00   76
 44  \w     41.00 102.00   0.50    3.50    --  111.50 -77.00  60.00  122
 45  \w     50.00 105.00   0.50    3.50    --  111.50 -94.00-180.00  110
 46  \w    103.00 176.00   0.50    3.50    --  111.50  45.00-150.00  146
 47  \w     42.00  67.00   0.50    3.50    --  111.50 -61.00  90.00   50
 48  \w     44.00  69.00   0.50    3.50    --  111.50 -61.00-120.00   50
 49  \w     44.00  69.00   0.50    3.50    --  111.50 -61.00  60.00   50
 50  \w    104.00 143.00   0.50    3.50    --  111.50 151.00 103.00   78
 51  \w     57.00 107.00   0.50    3.50    --  111.50-103.00-175.47  100
 52  \w    103.00 129.00   0.50    3.50    --  111.50 125.00 -30.00   52
 53  \w    134.00 160.00   0.50    3.50    --  111.50 125.00 -30.00   52
 54  \w    112.00 138.00   0.50    3.50    --  111.50  30.00 120.00   52
 55  \w    146.00 172.00   0.50    3.50    --  111.50  30.00 120.00   52
 56  \w     73.00 100.00   0.50    3.50    --  111.50-125.00  60.00   54
 57  \w    134.00 165.00   0.50    3.50    --  111.50 125.00-120.00   62
 58  \w     86.00 111.00   0.50    3.50    --  111.50-125.00 -60.00   50
 59  \w    141.00 167.00   0.50    3.50    --  111.50  30.00  60.00   52
 60  \w    104.00 129.00   0.50    3.50    --  111.50  15.00 -30.00   50
 61  \w    138.00 164.00   0.50    3.50    --  111.50  15.00 -30.00   52
 62  \w     63.00  89.00   0.50    3.50    --  111.50 -77.00-180.00   52
 63  \w     80.00 105.00   0.50    3.50    --  111.50 -94.00-150.00   50
 64  \w     66.00 117.00   0.50    3.50    --  111.50-133.00 -14.21  102
 65  \w     80.00 105.00   0.50    3.50    --  111.50 -94.00 -98.68   50
;
_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      -0.0356676000
_diffrn_orient_matrix_UB_12      0.1366000000
_diffrn_orient_matrix_UB_13      -0.0188700000
_diffrn_orient_matrix_UB_21      0.0718997000
_diffrn_orient_matrix_UB_22      0.0128644000
_diffrn_orient_matrix_UB_23      -0.1231257000
_diffrn_orient_matrix_UB_31      -0.2616216000
_diffrn_orient_matrix_UB_32      0.0076084000
_diffrn_orient_matrix_UB_33      -0.0124470000
_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  0.0349
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11962
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         81.117
_diffrn_reflns_theta_min         3.601
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.733
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       irregular
_exptl_crystal_F_000             364
_exptl_crystal_recrystallization_method 'crystallized from methanol'
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0956P)^2^+0.1023P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1498
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2923
_reflns_number_total             3406
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ce00063k2.cif
_cod_data_source_block           exp_654
_cod_depositor_comments
'Adding full bibliography for 7251818--7251826.cif.'
_cod_database_code               7251824
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H18N4O5
_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:
 C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C17(H17), C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              35282
_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 1.765
_oxdiff_exptl_absorpt_empirical_full_min 0.704