Di(hydroperoxy)adamantane Adducts: Synthesis, Characterization and Application as Oxidizers for the Direct Esterification of Aldehydes
Arp, Fabian Felix; Ashirov, Rahym; Bhuvanesh, Nattamai; Bluemel, Janet; Dalton Transactions  (2021) –; doi:10.1039/D1DT03243G

data_7708499
_publ_section_title
;
 Di(hydroperoxy)adamantane Adducts: Synthesis, Characterization and
 Application as Oxidizers for the Direct Esterification of Aldehydes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT03243G
_journal_year                    2021
_chemical_formula_moiety         'C18 H33 O P, C10 H15 O4'
_chemical_formula_sum            'C28 H48 O5 P'
_chemical_formula_weight         495.63
_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             2019-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-29 deposited with the CCDC.	2021-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                99.3060(10)
_cell_angle_beta                 96.0350(10)
_cell_angle_gamma                90.6870(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6844(3)
_cell_length_b                   11.1339(4)
_cell_length_c                   13.0829(5)
_cell_measurement_reflns_used    9176
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.436
_cell_measurement_theta_min      2.235
_cell_volume                     1383.78(8)
_computing_cell_refinement
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_data_reduction
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker PHOTON II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14566
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.234
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_correction_T_min  0.4023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1273 before and 0.0534 after correction. The Ratio of minimum to maximum transmission is 0.9345. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             542
_exptl_crystal_size_max          0.526
_exptl_crystal_size_mid          0.397
_exptl_crystal_size_min          0.322
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         4842
_refine_ls_number_restraints     821
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0435P)^2^+0.8664P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1015
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4456
_reflns_number_total             4842
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03243g2.cif
_cod_data_source_block           ffe409
_cod_database_code               7708499
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.933
_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 O(H) groups
2. Restrained distances
 O5-O4 \\sim O5A-O4A \\sim O3A-O2A \\sim O3-O2
 with sigma of 0.005
 O4-C19 \\sim O4A-C19A \\sim O2A-C19A \\sim O2-C19
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
O2 \\sim O3 \\sim O4 \\sim O5 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23
\\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim C28 \\sim O2A \\sim O3A \\sim O4A
\\sim O5A \\sim C19A \\sim C20A \\sim C21A \\sim C22A \\sim C23A \\sim C24A
\\sim C25A \\sim C26A \\sim C27A \\sim C28A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C19A) = Uanis(C19)
Uanis(O3) = Uanis(O3A)
Uanis(O5A) = Uanis(O5)
Uanis(C21A) = Uanis(C27)
4. Rigid body (RIGU) restrains
 O2, O3, O4, O5, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, O2A, O3A,
 O4A, O5A, C19A, C20A, C21A, C22A, C23A, C24A, C25A, C26A, C27A, C28A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Same fragment restrains
{O2, O3, O4, O5, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28} sigma for
1-2: 0.01, 1-3: 0.04
as
{O2A, O3A, O4A, O5A, C19A, C20A, C21A, C22A, C23A, C24A, C25A, C26A, C27A, C28A}
6. Others
 Sof(O2A)=Sof(O3A)=Sof(H3AA)=Sof(O4A)=Sof(O5A)=Sof(H5AA)=Sof(C19A)=Sof(C20A)=
 Sof(H20A)=Sof(C21A)=Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22A)=Sof(C23A)=
 Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(H25C)=Sof(H25D)=
 Sof(C26A)=Sof(H26C)=Sof(H26D)=Sof(C27A)=Sof(H27A)=Sof(C28A)=Sof(H28A)=1-FVAR(1)
 Sof(O2)=Sof(O3)=Sof(H3)=Sof(O4)=Sof(O5)=Sof(H5)=Sof(C19)=Sof(C20)=Sof(H20)=
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23A)=Sof(H23B)=
 Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=
 Sof(C27)=Sof(H27)=Sof(C28)=Sof(H28)=FVAR(1)
7.a Riding coordinates:
 O3(H3), O5(H5), O3A(H3AA), O5A(H5AA)
7.b Ternary CH refined with riding coordinates:
 C1(H1), C7(H7), C13(H13), C20(H20), C22(H22), C24(H24), C28(H28), C20A(H20A),
 C22A(H22A), C24A(H24A), C28A(H28A)
7.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B),
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B),
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C21(H21A,H21B),
  C23(H23A,H23B), C25(H25A,H25B), C26(H26A,H26B), C21A(H21C,H21D), C23A(H23C,
 H23D), C25A(H25C,H25D), C26A(H26C,H26D)
7.d Aromatic/amide H refined with riding coordinates:
 C27(H27), C27A(H27A)
;
_shelx_res_checksum              9793
_shelx_hkl_checksum              18684
_olex2_submission_special_instructions 'No special instructions were received'