A host–guest interaction activated Bobbitt oxidant for highly efficient oxidation of alcohols
Wu, Jinyang; Luo, Youran; Chen, Lingxuan; Sun, Xuan; Chen, Xinnan; Qin, Song; Feng, Wen; Li, Xiaowei; Yuan, Lihua; Chemical Communications  (2022) –; doi:10.1039/D2CC05027G

data_7130940
_publ_section_title
;
 A host--guest interaction activated Bobbitt oxidant for highly efficient
 oxidation of alcohols
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC05027G
_journal_year                    2022
_chemical_formula_moiety
'2(C84 H113.02 N6 O18), 2(C11 H21 N2 O2), 2(B F4), 4(C2 H3 N), 2(C H1.5 N), 5(H2 O)'
_chemical_formula_sum            'C200 H293.03 B2 F8 N22 O45'
_chemical_formula_weight         3899.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-07-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-19 deposited with the CCDC.	2022-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.284(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   23.8670(3)
_cell_length_b                   20.5849(3)
_cell_length_c                   23.4795(3)
_cell_measurement_reflns_used    26151
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.6080
_cell_measurement_theta_min      2.0690
_cell_volume                     10252.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_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(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.958
_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    -28.00  18.00   0.50    0.50    --   46.62 -19.00 -30.00   92
  2  \w    -11.00  15.00   0.50    0.50    --   46.62 -19.00  60.00   52
  3  \w     73.00 100.00   0.50    1.00    --  107.75 -77.00 -30.00   54
  4  \w     58.00  83.00   0.50    1.00    --  107.75 -94.00   0.00   50
  5  \w     80.00 120.00   0.50    1.00    --  107.75-143.00  23.00   80
  6  \w     42.00  67.00   0.50    0.50    --   46.62-143.00  23.00   50
  7  \w     35.00  69.00   0.50    1.00    --  107.75 -77.00 -30.00   68
  8  \w     39.00 112.00   0.50    1.00    --  107.75-125.00 -90.00  146
  9  \w     64.00 106.00   0.50    1.00    --  107.75-127.00-167.00   84
 10  \w     62.00 111.00   0.50    1.00    --  107.75-125.00-120.00   98
 11  \w     57.00  96.00   0.50    0.50    --   46.62-127.00-167.00   78
 12  \w     35.00 108.00   0.50    1.00    --  107.75-114.00-152.23  146
 13  \w     36.00  67.00   0.50    1.00    --  107.75 -61.00 -30.00   62
 14  \w    105.00 165.00   0.50    1.00    --  107.75  45.00-180.00  120
 15  \w     76.00 142.00   0.50    1.00    --  107.75 127.00 -91.00  132
 16  \w     98.00 148.00   0.50    1.00    --  107.75  45.00  60.00  100
 17  \w     69.00 100.00   0.50    0.50    --   46.62 143.00  78.00   62
 18  \w    -28.00  28.00   0.50    0.50    --  -46.62  19.00-180.00  112
 19  \w    -67.00 -32.00   0.50    1.00    -- -100.00  61.00 -90.00   70
 20  \w    -83.00 -57.00   0.50    0.50    --  -46.62 127.00 -91.00   52
 21  \w    -94.00 -69.00   0.50    1.00    -- -100.00 127.00 -91.00   50
 22  \w    -74.00 -39.00   0.50    1.00    -- -100.00  61.00  30.00   70
 23  \w    -54.00 -27.00   0.50    1.00    -- -100.00  45.00  60.00   54
 24  \w    -54.00 -27.00   0.50    1.00    -- -100.00  45.00  90.00   54
 25  \w    -53.00 -28.00   0.50    1.00    -- -100.00  45.00 150.00   50
 26  \w   -119.00 -94.00   0.50    0.50    --  -46.62-143.00  23.00   50
 27  \w   -117.00 -23.00   0.50    0.50    --  -46.62 -77.00-150.00  188
 28  \w   -148.00 -88.00   0.50    1.00    -- -100.00 -61.00-150.00  120
 29  \w   -146.00-105.00   0.50    1.00    -- -100.00-127.00-167.00   82
 30  \w   -166.00-116.00   0.50    1.00    -- -100.00 -30.00   0.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0554658000
_diffrn_orient_matrix_UB_12      0.0472934000
_diffrn_orient_matrix_UB_13      -0.0172308000
_diffrn_orient_matrix_UB_21      0.0460549000
_diffrn_orient_matrix_UB_22      0.0578496000
_diffrn_orient_matrix_UB_23      0.0194488000
_diffrn_orient_matrix_UB_31      -0.0087682000
_diffrn_orient_matrix_UB_32      0.0044994000
_diffrn_orient_matrix_UB_33      -0.0690873000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.1427
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            83534
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.284
_diffrn_reflns_theta_min         2.083
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             4178
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1390
_refine_ls_number_reflns         20836
_refine_ls_number_restraints     717
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1390
_refine_ls_R_factor_gt           0.0930
_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^)+(0.1295P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2433
_refine_ls_wR_factor_ref         0.2627
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9895
_reflns_number_total             20836
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05027g2.cif
_cod_data_source_block           wwz-wjy-1-100k
_cod_database_code               7130940
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
016aae837473c65dc33e15eb053bfb4b3f02526a28a
;
_diffrn_oxdiff_digest_hkl
;
019de4fdb961416118353a4bf0f0e351abd8af
;
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 F036-B03L = F02N-B03L = F00T-B03L = F00S-B03L = F00U-B03M = F0-B03M = F02O-
 B03M = F0AA-B03M
 1.2 with sigma of 0.01
 F0AA-F0
 2.2 with sigma of 0.02
 F036-F02N = F02O-F0
 2.2 with sigma of 0.02
 C100-C101
 1.45 with sigma of 0.01
 N10-C101
 1.15 with sigma of 0.01
 N10-C100
 2.4 with sigma of 0.01
 F00U-F0
 2.2 with sigma of 0.02
 O14-C76A = O14-C76 = C86-C76 = C86A-C76A = C98A-C86A = C98-C86 = C99A-C98A =
 C99-C98 = C94A-C86A = C94-C86 = C94-C92 = C94A-C92A
 1.48 with sigma of 0.01
 C99A-C86A
 2.5 with sigma of 0.02
 C94A-C76A
 2.5 with sigma of 0.02
 C86-C99
 2.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F036 \\sim F00S \\sim B03L \\sim F00T \\sim F02N \\sim F0 \\sim F0AA \\sim B03M
\\sim F00U \\sim F02O: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
C97 \\sim N9 \\sim C91 \\sim N10 \\sim C101 \\sim C100 \\sim C96 \\sim N11
\\sim C95: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C76 \\sim C86 \\sim C92 \\sim C94 \\sim C98 \\sim C99 \\sim C76A \\sim C86A
\\sim C92A \\sim C94A \\sim C98A \\sim C99A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(F036) \\sim Ueq, Uanis(F00S) \\sim Ueq, Uanis(B03L) \\sim Ueq,
Uanis(F00T) \\sim Ueq, Uanis(F02N) \\sim Ueq, Uanis(F0) \\sim Ueq, Uanis(F0AA)
\\sim Ueq, Uanis(B03M) \\sim Ueq, Uanis(F00U) \\sim Ueq, Uanis(F02O) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C95) \\sim Ueq, Uanis(N11) \\sim Ueq, Uanis(C96) \\sim Ueq, Uanis(N10)
\\sim Ueq, Uanis(C101) \\sim Ueq, Uanis(C100) \\sim Ueq, Uanis(N9) \\sim Ueq,
Uanis(C91) \\sim Ueq, Uanis(C97) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C76) \\sim Ueq, Uanis(C86) \\sim Ueq, Uanis(C92) \\sim Ueq, Uanis(C94)
\\sim Ueq, Uanis(C98) \\sim Ueq, Uanis(C99) \\sim Ueq, Uanis(C76A) \\sim Ueq,
Uanis(C86A) \\sim Ueq, Uanis(C92A) \\sim Ueq, Uanis(C94A) \\sim Ueq,
Uanis(C98A) \\sim Ueq, Uanis(C99A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 F0, F0AA, B03M, F00U, F02O, F036, F00S, B03L, F00T, F02N
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C96, N11, C95, N10, C101, C100, C97, N9, C91
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C76, C86, C92, C94, C98, C99, C76A, C86A, C92A, C94A, C98A, C99A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Others
 Sof(F0AA)=Sof(B03M)=Sof(F00U)=Sof(F02O)=Sof(F0)=1-FVAR(1)
 Sof(F00S)=Sof(F00T)=Sof(F02N)=Sof(F036)=Sof(B03L)=FVAR(1)
 Sof(C76A)=Sof(H76C)=Sof(H76D)=Sof(C86A)=Sof(H86A)=Sof(C92A)=Sof(H92D)=
 Sof(H92E)=Sof(H92F)=Sof(C94A)=Sof(H94C)=Sof(H94D)=Sof(C98A)=Sof(H98A)=
 Sof(H98B)=Sof(C99A)=Sof(H99D)=Sof(H99E)=Sof(H99F)=1-FVAR(2)
 Sof(C76)=Sof(H76A)=Sof(H76B)=Sof(C86)=Sof(H86)=Sof(C92)=Sof(H92A)=Sof(H92B)=
 Sof(H92C)=Sof(C94)=Sof(H94A)=Sof(H94B)=Sof(C98)=Sof(C99)=Sof(H99A)=Sof(H99B)=
 Sof(H99C)=FVAR(2)
 Fixed Sof: C100(0.5) H10A(0.5) H10B(0.5) H10C(0.5) C101(0.5) O22(0.5)
 H22A(0.5) H22B(0.5)
6.a Riding coordinates:
 O21(H21A,H21B), O22(H22A,H22B), O23(H23A,H23B)
6.b Ternary CH refined with riding coordinates:
 C26(H26), C35(H35), C53(H53), C57(H57), C67(H67), C70(H70), C86(H86),
 C86A(H86A)
6.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C19(H19A,H19B), C42(H42A,H42B), C48(H48A,H48B), C52(H52A,H52B),
 C54(H54A,H54B), C58(H58A,H58B), C60(H60A,H60B), C62(H62A,H62B), C66(H66A,H66B),
  C68(H68A,H68B), C71(H71A,H71B), C76(H76A,H76B), C77(H77A,H77B), C79(H79A,
 H79B), C80(H80A,H80B), C82(H82A,H82B), C88(H88A,H88B), C94(H94A,H94B),
 C76A(H76C,H76D), C94A(H94C,H94D), C98A(H98A,H98B)
6.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N4(H4), N5(H5), N6(H6), C2(H2A), N8(H8), C5(H5A),
 C14(H14), C15(H15), C16(H16), C20(H20), C36(H36), C37(H37), C40(H40), C44(H44),
  C46(H46), C50(H50)
6.e Idealised Me refined as rotating group:
 C47(H47A,H47B,H47C), C51(H51A,H51B,H51C), C55(H55A,H55B,H55C), C59(H59A,H59B,
 H59C), C63(H63A,H63B,H63C), C64(H64A,H64B,H64C), C65(H65A,H65B,H65C), C69(H69A,
 H69B,H69C), C72(H72A,H72B,H72C), C73(H73A,H73B,H73C), C74(H74A,H74B,H74C),
 C75(H75A,H75B,H75C), C78(H78A,H78B,H78C), C81(H81A,H81B,H81C), C83(H83A,H83B,
 H83C), C84(H84A,H84B,H84C), C85(H85A,H85B,H85C), C87(H87A,H87B,H87C), C89(H89A,
 H89B,H89C), C90(H90A,H90B,H90C), C92(H92A,H92B,H92C), C93(H93A,H93B,H93C),
 C95(H95A,H95B,H95C), C97(H97A,H97B,H97C), C99(H99A,H99B,H99C), C100(H10A,H10B,
 H10C), C92A(H92D,H92E,H92F), C99A(H99D,H99E,H99F)
;
_shelx_res_checksum              8522
_shelx_hkl_checksum              96605
_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 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.699