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_7708500
_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         'C21 H21 O P, C10 H16 O4'
_chemical_formula_sum            'C31 H37 O5 P'
_chemical_formula_weight         520.57
_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
_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                90
_cell_angle_beta                 106.362(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0424(17)
_cell_length_b                   11.7362(12)
_cell_length_c                   14.7397(16)
_cell_measurement_reflns_used    9151
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.606
_cell_measurement_theta_min      2.255
_cell_volume                     2662.8(5)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0710
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            109510
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.606
_diffrn_reflns_theta_min         2.182
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.5301
_exptl_absorpt_correction_T_min  0.3923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1317 before and 0.0984 after correction. The Ratio of minimum to maximum transmission is 0.7400. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.146
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         6163
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0369P)^2^+1.5583P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0999
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5287
_reflns_number_total             6163
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03243g2.cif
_cod_data_source_block           ffe408a
_cod_database_code               7708500
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.966
_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) groups, All O(H) groups
2. Shared sites
{C22, C22A}
3. Restrained distances
 O3A-O2A \\sim O3-O2 \\sim O5A-O4A \\sim O5-O4
 with sigma of 0.005
 O2-C22 \\sim O2A-C22 \\sim O4-C22 \\sim O4A-C22
 with sigma of 0.005
4. Uiso/Uaniso restraints and constraints
Uanis(O2A) = Uanis(O2)
Uanis(O4A) = Uanis(O4)
Uanis(O5A) = Uanis(O5)
Uanis(O3A) = Uanis(O3)
Uanis(C22A) = Uanis(C22)
Uanis(C27) = Uanis(C23A)
Uanis(C23) = Uanis(C27A)
Uanis(C31A) = Uanis(C31)
Uanis(C25A) = Uanis(C26)
Uanis(C26) = Uanis(C26A)
Uanis(C28) = Uanis(C28A)
Uanis(C29) = Uanis(C29A)
Uanis(C30A) = Uanis(C24)
5. Others
 Sof(O2A)=Sof(O3A)=Sof(H3AA)=Sof(O4A)=Sof(O5A)=Sof(H5AA)=Sof(C22A)=Sof(C23A)=
 Sof(H23A)=Sof(C24A)=Sof(H24C)=Sof(H24D)=Sof(C25A)=Sof(H25A)=Sof(C26A)=
 Sof(H26C)=Sof(H26D)=Sof(C27A)=Sof(H27A)=Sof(C28A)=Sof(H28C)=Sof(H28D)=
 Sof(C29A)=Sof(H29C)=Sof(H29D)=Sof(C30A)=Sof(H30C)=Sof(H30D)=Sof(C31A)=
 Sof(H31A)=1-FVAR(1)
 Sof(O2)=Sof(O3)=Sof(H3A)=Sof(O4)=Sof(O5)=Sof(H5A)=Sof(C22)=Sof(C23)=Sof(H23)=
 Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26A)=Sof(H26B)=
 Sof(C27)=Sof(H27)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(C29)=Sof(H29A)=Sof(H29B)=
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31)=FVAR(1)
6.a Riding coordinates:
 O3(H3A), O5(H5A), O3A(H3AA), O5A(H5AA)
6.b Ternary CH refined with riding coordinates:
 C23(H23), C25(H25), C27(H27), C31(H31), C23A(H23A), C25A(H25A), C27A(H27A),
 C31A(H31A)
6.c Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C26(H26A,H26B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,
 H30B), C24A(H24C,H24D), C26A(H26C,H26D), C28A(H28C,H28D), C29A(H29C,H29D),
 C30A(H30C,H30D)
6.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C20(H20)
6.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              81253
_shelx_hkl_checksum              43329
_olex2_submission_special_instructions 'No special instructions were received'