Photoinduced radical formation in hydrogen-bonded organic frameworks.
Almuhana, Asia R. Y.; Orton, Georgia R. F.; Rosenberg, Callum; Champness, Neil R.; Chemical communications (Cambridge, England) 60 (2024) 452–455; doi:10.1039/d3cc05236b

data_7132441
_publ_section_title
;
 Photoinduced radical formation in hydrogen-bonded organic frameworks.
;
_journal_issue                   4
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              452
_journal_page_last               455
_journal_paper_doi               10.1039/d3cc05236b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C15 H5 N O6, 3(H2 O), C8 H12 N4, O, 4.5[H2O]'
_chemical_formula_sum            'C23 H32 N5 O14.5'
_chemical_formula_weight         610.53
_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             2023-11-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-01 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                93.4340(10)
_cell_angle_beta                 95.1770(10)
_cell_angle_gamma                94.8900(10)
_cell_formula_units_Z            2
_cell_length_a                   7.08760(10)
_cell_length_b                   9.07010(10)
_cell_length_c                   22.17710(10)
_cell_measurement_reflns_used    26908
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.7530
_cell_measurement_theta_min      1.9920
_cell_volume                     1411.39(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_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    -83.00   0.00   0.50    1.00    --  -46.61 105.00  48.00  166
  2  \w      6.00  83.00   0.50    1.00    --   46.61-105.00 -51.00  154
  3  \w     29.00 107.00   0.50    4.00    --  101.75-105.00 -51.00  156
  4  \w   -107.00 -30.00   0.50    4.00    -- -103.00 105.00  48.00  154
  5  \w   -174.00 -86.00   0.50    4.00    -- -103.00-105.00 -51.00  176
  6  \w    -40.00  27.00   0.50    1.00    --  -46.61  37.00-150.00  134
  7  \w    -24.00  29.00   0.50    1.00    --  -46.61  19.00 -60.00  106
  8  \w    -24.00  29.00   0.50    1.00    --  -46.61  19.00 -30.00  106
  9  \w     24.00 118.00   0.50    1.00    --   46.61  77.00  60.00  188
 10  \w    -25.00  62.00   0.50    1.00    --   46.61 -57.00-180.00  174
 11  \w    -25.00  69.00   0.50    1.00    --   46.61 -77.00  90.00  188
 12  \w     29.00 106.00   0.50    4.00    --  101.75 -94.00-150.00  154
 13  \w     29.00 106.00   0.50    4.00    --  101.75 -94.00 120.00  154
 14  \w     29.00  73.00   0.50    4.00    --  101.75 -61.00 120.00   88
 15  \w     29.00  73.00   0.50    4.00    --  101.75 -61.00-150.00   88
 16  \w     29.00 112.00   0.50    4.00    --  101.75-125.00 120.00  166
 17  \w     79.00 175.00   0.50    4.00    --  101.75  77.00-180.00  192
 18  \w     29.00 108.00   0.50    4.00    --  101.75 -77.00 120.00  158
 19  \w     29.00 108.00   0.50    4.00    --  101.75 -77.00 -60.00  158
 20  \w     82.00 175.00   0.50    4.00    --  101.75 125.00   0.00  186
 21  \w     29.00 112.00   0.50    4.00    --  101.75-125.00 -60.00  166
 22  \w     92.00 175.00   0.50    4.00    --  101.75 105.00  48.00  166
 23  \w     29.00  73.00   0.50    4.00    --  101.75 -61.00-180.00   88
 24  \w     29.00 106.00   0.50    4.00    --  101.75 -94.00 -60.00  154
 25  \w     29.00  73.00   0.50    4.00    --  101.75 -61.00   0.00   88
 26  \w   -104.00 -30.00   0.50    4.00    -- -103.00  77.00-180.00  148
 27  \w   -174.00 -83.00   0.50    4.00    -- -103.00 -69.00  29.68  182
 28  \w   -174.00 -89.00   0.50    4.00    -- -103.00 -51.00 -18.37  170
 29  \w   -174.00 -89.00   0.50    4.00    -- -103.00 -54.00 -33.19  170
 30  \w   -112.00 -30.00   0.50    4.00    -- -103.00 125.00  60.00  164
 31  \w     24.00 118.00   0.50    1.00    --   46.61  77.00 -90.00  188
 32  \w     32.00 118.00   0.50    1.00    --   46.61  57.00   0.00  172
 33  \w     32.00 118.00   0.50    1.00    --   46.61  57.00-120.00  172
 34  \w     32.00 118.00   0.50    1.00    --   46.61  57.00 150.00  172
 35  \w     24.00 118.00   0.50    1.00    --   46.61  77.00 150.00  188
 36  \w     24.00  53.00   0.50    1.00    --   46.61  77.00-180.00   58
 37  \w    -55.00 -24.00   0.50    1.00    --  -46.61 -77.00   0.00   62
 38  \w    -60.00 -33.00   0.50    1.00    --  -46.61 -57.00 150.00   54
 39  \w    -55.00 -24.00   0.50    1.00    --  -46.61 -77.00  60.00   62
 40  \w    -81.00 -34.00   0.50    1.00    --  -46.61 -37.00 -90.00   94
 41  \w    -67.00 -34.00   0.50    1.00    --  -46.61 -37.00 120.00   66
 42  \w    -60.00 -33.00   0.50    1.00    --  -46.61 -57.00-150.00   54
 43  \w     91.00 119.00   0.50    1.00    --   46.61  37.00 -60.00   56
 44  \w     53.00  79.00   0.50    1.00    --   46.61  37.00 -60.00   52
 45  \w     26.00  54.00   0.50    1.00    --   46.61  77.00  90.00   56
 46  \w     28.00  54.00   0.50    1.00    --   46.61  77.00-150.00   52
 47  \w     25.00  51.00   0.50    1.00    --   46.61  77.00 -30.00   52
 48  \w     35.00  89.00   0.50    1.00    --   46.61  19.00  30.00  108
 49  \w     24.00  50.00   0.50    1.00    --   46.61  77.00-120.00   52
 50  \w     25.00  69.00   0.50    1.00    --   46.61  77.00   0.00   88
 51  \w   -109.00 -82.00   0.50    4.00    -- -103.00 -74.00 -24.17   54
 52  \w   -147.00 -86.00   0.50    4.00    -- -103.00 -66.00 131.08  122
 53  \w   -172.00-146.00   0.50    4.00    -- -103.00 -81.00-115.87   52
 54  \w   -117.00 -86.00   0.50    4.00    -- -103.00 -67.00  47.27   62
 55  \w   -170.00-128.00   0.50    4.00    -- -103.00 -67.00  47.27   84
 56  \w   -107.00 -80.00   0.50    4.00    -- -103.00 -77.00 120.00   54
 57  \w   -173.00-140.00   0.50    4.00    -- -103.00 -74.00 -88.49   66
 58  \w   -115.00 -86.00   0.50    4.00    -- -103.00 -61.00 -90.00   58
 59  \w   -109.00 -84.00   0.50    4.00    -- -103.00 -68.00 -52.64   50
 60  \w   -149.00 -83.00   0.50    4.00    -- -103.00 -70.00-112.86  132
 61  \w   -107.00 -81.00   0.50    4.00    -- -103.00 -77.00-180.00   52
 62  \w   -106.00 -80.00   0.50    4.00    -- -103.00 -76.00  -3.91   52
 63  \w   -160.00-134.00   0.50    4.00    -- -103.00 -61.00  60.00   52
 64  \w   -111.00 -86.00   0.50    4.00    -- -103.00 -61.00  60.00   50
 65  \w   -107.00 -81.00   0.50    4.00    -- -103.00 -77.00  30.00   52
 66  \w   -174.00 -81.00   0.50    4.00    -- -103.00 -78.00-148.85  186
 67  \w   -143.00-117.00   0.50    4.00    -- -103.00 -61.00 -90.00   52
 68  \w   -105.00 -78.00   0.50    4.00    -- -103.00 -82.00 137.22   54
 69  \w   -138.00 -84.00   0.50    4.00    -- -103.00 -68.00 140.78  108
 70  \w   -158.00 -87.00   0.50    4.00    -- -103.00 -61.00 150.00  142
 71  \w   -110.00 -84.00   0.50    4.00    -- -103.00 -68.00 -39.93   52
 72  \w   -114.00 -87.00   0.50    4.00    -- -103.00 -61.00 -30.00   54
 73  \w   -106.00 -80.00   0.50    4.00    -- -103.00 -79.00 161.01   52
 74  \w   -105.00 -80.00   0.50    4.00    -- -103.00 -77.00 -95.02   50
 75  \w   -110.00 -84.00   0.50    4.00    -- -103.00 -68.00 -58.99   52
 76  \w   -166.00-139.00   0.50    4.00    -- -103.00 -79.00 161.01   54
 77  \w   -108.00 -83.00   0.50    4.00    -- -103.00 -69.00  55.45   50
 78  \w   -129.00 -91.00   0.50    4.00    -- -103.00 -48.00  -8.47   76
 79  \w   -106.00 -80.00   0.50    4.00    -- -103.00 -77.00  45.42   52
 80  \w   -111.00 -86.00   0.50    4.00    -- -103.00 -61.00  90.00   50
 81  \w   -107.00 -80.00   0.50    4.00    -- -103.00 -78.00-113.42   54
 82  \w   -105.00 -79.00   0.50    4.00    -- -103.00 -80.00 100.99   52
 83  \w   -170.00-120.00   0.50    4.00    -- -103.00 -80.00-160.96  100
 84  \w   -108.00 -80.00   0.50    4.00    -- -103.00 -80.00-160.96   56
 85  \w   -164.00-137.00   0.50    4.00    -- -103.00 -61.00  90.00   54
 86  \w   -105.00 -79.00   0.50    4.00    -- -103.00 -81.00-115.87   52
 87  \w   -107.00 -81.00   0.50    4.00    -- -103.00 -75.00-141.01   52
 88  \w   -116.00 -86.00   0.50    4.00    -- -103.00 -64.00  77.65   60
 89  \w   -115.00 -85.00   0.50    4.00    -- -103.00 -66.00 172.34   60
 90  \w   -107.00 -81.00   0.50    4.00    -- -103.00 -74.00 -88.49   52
 91  \w   -109.00 -79.00   0.50    4.00    -- -103.00 -80.00-128.03   60
 92  \w   -109.00 -82.00   0.50    4.00    -- -103.00 -77.00 -60.00   54
 93  \w   -120.00 -34.00   0.50    1.00    --  -46.61 -37.00-180.00  172
 94  \w   -121.00 -34.00   0.50    1.00    --  -46.61 -19.00 -60.00  174
 95  \w   -118.00 -24.00   0.50    1.00    --  -46.61 -77.00  60.00  188
 96  \w   -118.00 -32.00   0.50    1.00    --  -46.61 -57.00 -90.00  172
 97  \w     24.00 118.00   0.50    1.00    --   46.61  77.00-150.00  188
 98  \w    -26.00  44.00   0.50    1.00    --   46.61 -37.00 -60.00  140
 99  \w     24.00 118.00   0.50    1.00    --   46.61  77.00   0.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            47656
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.144
_diffrn_reflns_theta_min         2.005
_exptl_absorpt_coefficient_mu    1.043
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       plate
_exptl_crystal_F_000             642
_exptl_crystal_preparation       'see experimental'
_exptl_crystal_recrystallization_method 'see experimental'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0918P)^2^+0.8735P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1670
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5071
_reflns_number_total             5703
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05236b2.cif
_cod_data_source_block           2022ncs0045z
_cod_depositor_comments
'Adding full bibliography for 7132441--7132443.cif.'
_cod_original_formula_sum        'C23 H32 N5 O14.50'
_cod_database_code               7132441
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.903
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Sof(O9A)=1-FVAR(1)
 Sof(O9)=FVAR(1)
 Fixed Sof: O11(0.5) H11A(0.5) H11B(0.5) O7(0.5) H7A(0.5) H7B(0.5)
3.a Free rotating group:
 O8(H8A,H8B), O10(H10A,H10B), O11(H11A,H11B), O7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C16(H16), C19(H19), C22(H22), C3(H3), C4(H4), C6(H6),
 C7(H7)
3.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 89 electrons were 
found in a volume of 279\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
4.5[H2O] per Asymmetric Unit 
which account for 90 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              10627
_shelx_hkl_checksum              1096
_shelx_fab_checksum              14923
_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
- Detector area scaling
;