A water-soluble aza-adamantyl nitroxide radical and its complexes with β-cyclodextrin derivatives
Zhao, Yani; Duan, Ran; Guo, Weijie; Lyu, Lele; Liu, Xiaoyu; Jiang, Hua; Wang, Ying; New Journal of Chemistry 48 (2024) 12681–12687; doi:10.1039/D4NJ01211A

data_7063272
_publ_section_title
;
 A water-soluble aza-adamantyl nitroxide radical and its complexes with
 \b-cyclodextrin derivatives
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12681
_journal_page_last               12687
_journal_paper_doi               10.1039/D4NJ01211A
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         '7(C9 H14 N O2), 4.83(H2 O)'
_chemical_formula_sum            'C63 H107.65 N7 O18.82'
_chemical_formula_weight         1264.40
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2jyrdn
_audit_creation_date             2024-05-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-06-04 deposited with the CCDC.	2024-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                101.7560(10)
_cell_angle_beta                 90.9180(10)
_cell_angle_gamma                90.584(2)
_cell_formula_units_Z            2
_cell_length_a                   6.63740(10)
_cell_length_b                   16.5830(3)
_cell_length_c                   28.8082(4)
_cell_measurement_reflns_used    23104
_cell_measurement_temperature    100.00(13)
_cell_measurement_theta_max      76.1160
_cell_measurement_theta_min      3.8060
_cell_volume                     3103.66(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(13)
_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 0.959
_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    -60.00  -6.00   0.50    2.27    --  -48.75 112.00 -77.00  108
  2  \w     34.00  68.00   0.50    2.27    --   48.75-112.00-170.00   68
  3  \w   -128.00 -94.00   0.50    9.08    -- -102.00-112.00-170.00   68
  4  \w   -167.00-136.00   0.50    9.08    -- -102.00-112.00-170.00   62
  5  \w   -108.00 -81.00   0.50    9.08    -- -102.00 112.00 -77.00   54
  6  \w     84.00 136.00   0.50    9.08    --  102.75 112.00 -77.00  104
  7  \w    -12.00  14.00   0.50    2.27    --  -48.75  19.00 -90.00   52
  8  \w    -11.00  25.00   0.50    2.27    --  -48.75  19.00   0.00   72
  9  \w   -121.00 -78.00   0.50    2.27    --  -48.75-125.00 -30.00   86
 10  \w    -92.00 -58.00   0.50    2.27    --  -48.75 125.00  30.00   68
 11  \w    -20.00  24.00   0.50    2.27    --  -48.75  19.00  60.00   88
 12  \w    -45.00 -13.00   0.50    2.27    --  -48.75 125.00  30.00   64
 13  \w     76.00 101.00   0.50    2.27    --   48.75 125.00 120.00   50
 14  \w    -22.00  53.00   0.50    2.27    --   48.75 -57.00-180.00  150
 15  \w     30.00 120.00   0.50    2.27    --   48.75  77.00 -60.00  180
 16  \w    -63.00 -31.00   0.50    9.08    -- -102.00  57.00 -90.00   64
 17  \w   -130.00-103.00   0.50    9.08    -- -102.00 -99.00  30.00   54
 18  \w   -173.00-147.00   0.50    9.08    -- -102.00 -99.00  30.00   52
 19  \w   -172.00-128.00   0.50    9.08    -- -102.00 -37.00 120.00   88
 20  \w   -167.00 -91.00   0.50    9.08    -- -102.00 -57.00 -90.00  152
 21  \w    -55.00 -30.00   0.50    9.08    -- -102.00  57.00-180.00   50
 22  \w     35.00 106.00   0.50    9.08    --  102.75 -77.00  60.00  142
 23  \w     42.00  68.00   0.50    9.08    --  102.75 -57.00-120.00   52
 24  \w     96.00 172.00   0.50    9.08    --  102.75  37.00-180.00  152
 25  \w     37.00  64.00   0.50    9.08    --  102.75-125.00 150.00   54
 26  \w    129.00 167.00   0.50    9.08    --  102.75  37.00-150.00   76
 27  \w     37.00 107.00   0.50    9.08    --  102.75 -77.00-180.00  140
 28  \w     34.00  61.00   0.50    9.08    --  102.75 -57.00 -30.00   54
 29  \w     34.00 111.00   0.50    9.08    --  102.75-125.00  60.00  154
 30  \w     82.00 109.00   0.50    9.08    --  102.75 -99.00-180.00   54
 31  \w     54.00  81.00   0.50    9.08    --  102.75 -99.00-180.00   54
 32  \w     80.00 116.00   0.50    9.08    --  102.75-125.00 150.00   72
 33  \w     32.00 110.00   0.50    9.08    --  102.75-125.00  30.00  156
 34  \w     32.00 100.00   0.50    9.08    --  102.75 -99.00  60.00  136
 35  \w     68.00 109.00   0.50    9.08    --  102.75 -99.00 -90.00   82
 36  \w    125.00 173.00   0.50    9.08    --  102.75  77.00  60.00   96
 37  \w     84.00 110.00   0.50    9.08    --  102.75  77.00  60.00   52
 38  \w     31.00  67.00   0.50    9.08    --  102.75 -57.00  90.00   72
 39  \w     34.00  65.00   0.50    9.08    --  102.75 -57.00-180.00   62
 40  \w     32.00  67.00   0.50    9.08    --  102.75 -57.00 -60.00   70
 41  \w     99.00 171.00   0.50    9.08    --  102.75  37.00  90.00  144
 42  \w     62.00 112.00   0.50    9.08    --  102.75-112.00-170.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0523381000
_diffrn_orient_matrix_UB_12      -0.0848362000
_diffrn_orient_matrix_UB_13      -0.0300709000
_diffrn_orient_matrix_UB_21      -0.0891935000
_diffrn_orient_matrix_UB_22      0.0257312000
_diffrn_orient_matrix_UB_23      -0.0444185000
_diffrn_orient_matrix_UB_31      0.2078504000
_diffrn_orient_matrix_UB_32      0.0338620000
_diffrn_orient_matrix_UB_33      -0.0103608000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            40168
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.541
_diffrn_reflns_theta_min         3.407
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.816
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       needle
_exptl_crystal_F_000             1370
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane and chloroform'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     951
_refine_ls_number_reflns         12532
_refine_ls_number_restraints     163
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0736P)^2^+1.5049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1423
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10576
_reflns_number_total             12532
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj01211a2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7063272.cif.'
_cod_database_code               7063272
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N'
_diffrn_oxdiff_digest_frames
;
01294298c94f608cc37c37e2662e02d9d6000270f14
;
_diffrn_oxdiff_digest_hkl
;
011d93d432373c87f6defb7cd641a20608872d
;
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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,H,H,H,H,H) groups, All O(H) groups
2. Restrained distances
 O19-H19A = O19-H19B
 0.87 with sigma of 0.02
 O18-H18C = O18-H18D
 0.87 with sigma of 0.02
 O17-H17A = O17-H17B
 0.87 with sigma of 0.02
 O16-H16D = O16-H16C
 0.87 with sigma of 0.02
 O15-H15A = O15-H15B
 0.87 with sigma of 0.02
 H19A-H19B
 1.38 with sigma of 0.04
 H18C-H18D
 1.38 with sigma of 0.04
 H17A-H17B
 1.38 with sigma of 0.04
 H16D-H16C
 1.38 with sigma of 0.04
 H15A-H15B
 1.38 with sigma of 0.04
 C53-C54 \\sim C53A-C54A
 with sigma of 0.02
 C53-C55 \\sim C53A-C55A
 with sigma of 0.02
 C53-C59 \\sim C53A-C59A
 with sigma of 0.02
 C53-O13 \\sim C53A-O13A
 with sigma of 0.02
 C54-C58 \\sim C54A-C58A
 with sigma of 0.02
 C55-C56 \\sim C55A-C56A
 with sigma of 0.02
 C56-C57 \\sim C56A-C57A
 with sigma of 0.02
 C56-C61 \\sim C56A-C61A
 with sigma of 0.02
 C57-C58 \\sim C57A-C58A
 with sigma of 0.02
 C58-N7 \\sim C58A-N7A
 with sigma of 0.02
 C59-C60 \\sim C59A-C60A
 with sigma of 0.02
 C60-C61 \\sim C60A-C61A
 with sigma of 0.02
 C60-N7 \\sim C60A-N7A
 with sigma of 0.02
 N7-O14 \\sim N7A-O14A
 with sigma of 0.02
 C53-C56 \\sim C53A-C56A
 with sigma of 0.04
 C53-C58 \\sim C53A-C58A
 with sigma of 0.04
 C53-C60 \\sim C53A-C60A
 with sigma of 0.04
 C54-C55 \\sim C54A-C55A
 with sigma of 0.04
 C54-C57 \\sim C54A-C57A
 with sigma of 0.04
 C54-C59 \\sim C54A-C59A
 with sigma of 0.04
 C54-N7 \\sim C54A-N7A
 with sigma of 0.04
 C54-O13 \\sim C54A-O13A
 with sigma of 0.04
 C55-C57 \\sim C55A-C57A
 with sigma of 0.04
 C55-C59 \\sim C55A-C59A
 with sigma of 0.04
 C55-C61 \\sim C55A-C61A
 with sigma of 0.04
 C55-O13 \\sim C55A-O13A
 with sigma of 0.04
 C56-C58 \\sim C56A-C58A
 with sigma of 0.04
 C56-C60 \\sim C56A-C60A
 with sigma of 0.04
 C57-C61 \\sim C57A-C61A
 with sigma of 0.04
 C57-N7 \\sim C57A-N7A
 with sigma of 0.04
 C58-C60 \\sim C58A-C60A
 with sigma of 0.04
 C58-O14 \\sim C58A-O14A
 with sigma of 0.04
 C59-C61 \\sim C59A-C61A
 with sigma of 0.04
 C59-N7 \\sim C59A-N7A
 with sigma of 0.04
 C59-O13 \\sim C59A-O13A
 with sigma of 0.04
 C60-O14 \\sim C60A-O14A
 with sigma of 0.04
 C61-N7 \\sim C61A-N7A
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C54A, N7A, C58A, C60A, O14A, C57A, C59A, C61A, C53A, C56A, C55A, O13A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(N7A)=Sof(C53A)=Sof(C54A)=Sof(H54C)=Sof(H54D)=Sof(C55A)=Sof(H55C)=
 Sof(H55D)=Sof(C59A)=Sof(H59C)=Sof(H59D)=Sof(O13A)=Sof(H13B)=Sof(C58A)=
 Sof(H58A)=Sof(C56A)=Sof(H56A)=Sof(C60A)=Sof(H60A)=Sof(C57A)=Sof(H57C)=
 Sof(H57D)=Sof(C61A)=Sof(H61C)=Sof(H61D)=Sof(O14A)=1-FVAR(1)
 Sof(C53)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(C56)=
 Sof(H56)=Sof(C57)=Sof(H57A)=Sof(H57B)=Sof(C58)=Sof(H58)=Sof(C59)=Sof(H59A)=
 Sof(H59B)=Sof(C60)=Sof(H60)=Sof(C61)=Sof(H61A)=Sof(H61B)=Sof(N7)=Sof(O13)=
 Sof(H13A)=Sof(O14)=Sof(O19)=Sof(H19A)=Sof(H19B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C9(H9), C13(H13), C15(H15), C17(H17), C22(H22), C24(H24),
 C26(H26), C31(H31), C34(H34), C39(H39), C41(H41), C43(H43), C47(H47), C49(H49),
  C51(H51), C56(H56), C58(H58), C60(H60), C65(H65), C58A(H58A), C56A(H56A),
 C60A(H60A)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,
 H10B), C12(H12A,H12B), C14(H14A,H14B), C16(H16A,H16B), C18(H18A,H18B),
 C20(H20A,H20B), C21(H21A,H21B), C23(H23A,H23B), C25(H25A,H25B), C27(H27A,H27B),
  C29(H29A,H29B), C30(H30A,H30B), C32(H32A,H32B), C33(H33A,H33B), C36(H36A,
 H36B), C37(H37A,H37B), C38(H38A,H38B), C40(H40A,H40B), C42(H42A,H42B),
 C45(H45A,H45B), C46(H46A,H46B), C48(H48A,H48B), C50(H50A,H50B), C52(H52A,H52B),
  C54(H54A,H54B), C55(H55A,H55B), C57(H57A,H57B), C59(H59A,H59B), C61(H61A,
 H61B), C66(H66A,H66B), C54A(H54C,H54D), C55A(H55C,H55D), C59A(H59C,H59D),
 C57A(H57C,H57D), C61A(H61C,H61D)
5.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4A), O6(H6A), O8(H8), O10(H10), O11(H11), O13(H13A), O13A(H13B)
;
_shelx_res_checksum              20434
_shelx_hkl_checksum              83266
_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 1.587
_oxdiff_exptl_absorpt_empirical_full_min 0.473