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_7132443
_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, C8 H12 N4, C4 H4 N O, 4(H2 O)'
_chemical_formula_sum            'C27 H29 N6 O11'
_chemical_formula_weight         613.56
_chemical_name_systematic        HOF_2
_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             2023-10-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-10-24 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                88.4100(10)
_cell_angle_beta                 87.4730(10)
_cell_angle_gamma                83.4320(10)
_cell_formula_units_Z            2
_cell_length_a                   7.13610(10)
_cell_length_b                   9.06550(10)
_cell_length_c                   20.9919(3)
_cell_measurement_reflns_used    39448
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      78.8720
_cell_measurement_theta_min      4.1590
_cell_volume                     1347.44(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_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    -76.00  23.00   0.50    2.00    --  -49.01  88.00-160.00  198
  2  \w    -21.00  76.00   0.50    2.00    --   49.01 -88.00  82.00  194
  3  \w   -117.00 -18.00   0.50   10.00    --  -90.00  88.00-160.00  198
  4  \w   -161.00 -79.00   0.50   10.00    --  -90.00 -88.00  82.00  164
  5  \w    101.00 178.00   0.50   10.00    --  111.50  88.00-160.00  154
  6  \w     40.00 138.00   0.50   10.00    --  111.50 -88.00  82.00  196
  7  \w   -120.00 -94.00   0.50    2.00    --  -49.01 -57.00   0.00   52
  8  \w   -120.00 -94.00   0.50    2.00    --  -49.01 -57.00 150.00   52
  9  \w   -120.00 -94.00   0.50    2.00    --  -49.01 -57.00  60.00   52
 10  \w    -34.00  25.00   0.50    2.00    --  -49.01  19.00 120.00  118
 11  \w   -120.00 -94.00   0.50    2.00    --  -49.01 -57.00  30.00   52
 12  \w    -24.00  26.00   0.50    2.00    --   49.01 -19.00   0.00  100
 13  \w    -24.00  26.00   0.50    2.00    --   49.01 -19.00 150.00  100
 14  \w     94.00 121.00   0.50    2.00    --   49.01  57.00-150.00   54
 15  \w    -55.00 -18.00   0.50   10.00    --  -90.00  45.00-150.00   74
 16  \w    -75.00 -18.00   0.50   10.00    --  -90.00  61.00 150.00  114
 17  \w   -161.00-105.00   0.50   10.00    --  -90.00 -77.00 150.00  112
 18  \w   -161.00-105.00   0.50   10.00    --  -90.00 -77.00-180.00  112
 19  \w    -75.00 -18.00   0.50   10.00    --  -90.00  61.00 -30.00  114
 20  \w    101.00 178.00   0.50   10.00    --  111.50  30.00 -60.00  154
 21  \w     40.00 105.00   0.50   10.00    --  111.50 -95.00  60.00  130
 22  \w     40.00 108.00   0.50   10.00    --  111.50-110.00 -48.66  136
 23  \w     40.00 105.00   0.50   10.00    --  111.50 -95.00  30.00  130
 24  \w    101.00 178.00   0.50   10.00    --  111.50  15.00  30.00  154
 25  \w     95.00 178.00   0.50   10.00    --  111.50 125.00 -30.00  166
 26  \w     40.00  67.00   0.50   10.00    --  111.50 -61.00   0.00   54
 27  \w     40.00 111.00   0.50   10.00    --  111.50-125.00 -30.00  142
 28  \w     40.00 111.00   0.50   10.00    --  111.50-125.00  30.00  142
 29  \w     40.00 105.00   0.50   10.00    --  111.50 -95.00-150.00  130
 30  \w     40.00  97.00   0.50   10.00    --  111.50 -77.00 120.00  114
 31  \w    101.00 178.00   0.50   10.00    --  111.50  45.00  90.00  154
 32  \w     40.00  67.00   0.50   10.00    --  111.50 -61.00-180.00   54
 33  \w     98.00 178.00   0.50   10.00    --  111.50  61.00-120.00  160
 34  \w     40.00  67.00   0.50   10.00    --  111.50 -61.00 -60.00   54
 35  \w     40.00 105.00   0.50   10.00    --  111.50 -95.00-120.00  130
 36  \w     40.00 109.00   0.50   10.00    --  111.50-117.00  35.61  138
 37  \w     40.00  67.00   0.50   10.00    --  111.50 -61.00 120.00   54
 38  \w    101.00 178.00   0.50   10.00    --  111.50  45.00 150.00  154
 39  \w     40.00 108.00   0.50   10.00    --  111.50-109.00-168.57  136
 40  \w    101.00 178.00   0.50   10.00    --  111.50  30.00-150.00  154
 41  \w     40.00  97.00   0.50   10.00    --  111.50 -77.00  60.00  114
 42  \w    101.00 178.00   0.50   10.00    --  111.50  15.00-120.00  154
 43  \w     40.00 111.00   0.50   10.00    --  111.50-125.00 -60.00  142
 44  \w     40.00 111.00   0.50   10.00    --  111.50-125.00   0.00  142
 45  \w     40.00 105.00   0.50   10.00    --  111.50 -95.00  90.00  130
 46  \w     40.00  67.00   0.50   10.00    --  111.50 -61.00  90.00   54
 47  \w     40.00  67.00   0.50   10.00    --  111.50 -61.00-120.00   54
 48  \w   -120.00 -37.00   0.50    2.00    --  -49.01 -51.00 -40.03  166
 49  \w   -120.00 -38.00   0.50    2.00    --  -49.01 -45.00  59.20  164
 50  \w   -120.00 -37.00   0.50    2.00    --  -49.01 -50.00 114.71  166
 51  \w   -121.00 -39.00   0.50    2.00    --  -49.01 -38.00   0.00  164
 52  \w   -120.00 -94.00   0.50    2.00    --  -49.01 -57.00  90.00   52
 53  \w   -120.00 -37.00   0.50    2.00    --  -49.01 -49.00 167.14  166
 54  \w   -121.00 -39.00   0.50    2.00    --  -49.01 -38.00-150.00  164
 55  \w     37.00 121.00   0.50    2.00    --   49.01  52.00 -54.38  168
 56  \w   -161.00 -78.00   0.50   10.00    --  -90.00 -49.00 -48.31  166
 57  \w   -161.00 -78.00   0.50   10.00    --  -90.00 -51.00-158.42  166
 58  \w   -161.00 -80.00   0.50   10.00    --  -90.00 -52.00  -4.89  162
 59  \w   -161.00 -78.00   0.50   10.00    --  -90.00 -50.00  13.54  166
 60  \w   -161.00 -78.00   0.50   10.00    --  -90.00 -50.00 -28.63  166
 61  \w   -161.00 -78.00   0.50   10.00    --  -90.00 -49.00-148.89  166
 62  \w   -161.00 -78.00   0.50   10.00    --  -90.00 -49.00  58.47  166
 63  \w   -161.00 -85.00   0.50   10.00    --  -90.00 -53.00-171.35  152
 64  \w   -161.00 -78.00   0.50   10.00    --  -90.00 -50.00  86.42  166
 65  \w   -161.00 -78.00   0.50   10.00    --  -90.00 -51.00 -89.69  166
 66  \w   -161.00 -79.00   0.50   10.00    --  -90.00 -45.00 150.00  164
 67  \w   -161.00 -78.00   0.50   10.00    --  -90.00 -51.00  45.32  166
 68  \w   -161.00 -78.00   0.50   10.00    --  -90.00 -50.00 106.62  166
 69  \w   -161.00 -78.00   0.50   10.00    --  -90.00 -50.00 127.79  166
 70  \w   -161.00 -78.00   0.50   10.00    --  -90.00 -50.00-121.67  166
 71  \w   -161.00 -78.00   0.50   10.00    --  -90.00 -51.00 -62.02  166
 72  \w     98.00 178.00   0.50   10.00    --  111.50  61.00  60.00  160
 73  \w    101.00 178.00   0.50   10.00    --  111.50  45.00-150.00  154
 74  \w     98.00 178.00   0.50   10.00    --  111.50  61.00 -30.00  160
 75  \w     98.00 178.00   0.50   10.00    --  111.50  61.00 150.00  160
 76  \w    101.00 178.00   0.50   10.00    --  111.50  45.00 120.00  154
 77  \w    105.00 178.00   0.50   10.00    --  111.50  77.00 -90.00  146
 78  \w     98.00 178.00   0.50   10.00    --  111.50  61.00   0.00  160
 79  \w     97.00 178.00   0.50   10.00    --  111.50  60.00  40.10  162
 80  \w    101.00 178.00   0.50   10.00    --  111.50  30.00 -30.00  154
 81  \w     98.00 151.00   0.50   10.00    --  111.50  61.00-150.00  106
 82  \w    101.00 178.00   0.50   10.00    --  111.50  45.00  30.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            56339
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.085
_diffrn_reflns_theta_min         4.217
_exptl_absorpt_coefficient_mu    1.014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       plate
_exptl_crystal_F_000             642
_exptl_crystal_preparation       'see experimental'
_exptl_crystal_recrystallization_method 'see experimental'
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         5728
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0468P)^2^+1.0838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5421
_reflns_number_total             5728
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05236b2.cif
_cod_data_source_block           ov_hofs2_auto
_cod_depositor_comments
'Adding full bibliography for 7132441--7132443.cif.'
_cod_database_code               7132443
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.961
_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) groups, All O(H,H) groups
2. Restrained distances
 O9-H9A = O9-H9B
 0.87 with sigma of 0.02
 O10-H10A = O10-H10B
 0.87 with sigma of 0.02
 O8-H8A
 0.87 with sigma of 0.02
 O11-H11A = O11-H11B
 0.87 with sigma of 0.02
 H9A-H9B
 1.38 with sigma of 0.04
 H10A-H10B
 1.38 with sigma of 0.04
 H11A-H11B
 1.38 with sigma of 0.04
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C8(H8), C12(H12), C13(H13), C18(H18), C19(H19), C21(H21),
 C22(H22), C26(H26), C27(H27)
3.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B), N5(H5A,H5B), N6(H6A,H6B)
;
_shelx_res_checksum              10687
_shelx_hkl_checksum              42482
_olex2_exptl_crystal_mounting_method 'fomblin on micromount'
_olex2_submission_original_sample_id HOF_2
_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
;