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_7708501
_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, 1(C10 H16 O4)'
_chemical_formula_sum            'C31 H37 O5 P'
_chemical_formula_weight         520.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-19
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.0842(16)
_cell_length_b                   11.7871(9)
_cell_length_c                   21.7655(17)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      26.745
_cell_measurement_theta_min      2.189
_cell_volume                     5409.2(7)
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0467
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            57147
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.871
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1432 before and 0.0560 after correction. The Ratio of minimum to maximum transmission is 0.9285. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         4759
_refine_ls_number_restraints     807
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0417P)^2^+2.3609P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0945
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3905
_reflns_number_total             4759
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03243g2.cif
_cod_data_source_block           ffe407a
_cod_database_code               7708501
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.935
_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. Restrained distances
 O5A-O4A \\sim O5-O4 \\sim O3-O2 \\sim O3A-O2A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O2 \\sim O3 \\sim O4 \\sim O5 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26
\\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim O2A \\sim O3A \\sim O4A
\\sim O5A \\sim C22A \\sim C23A \\sim C24A \\sim C25A \\sim C26A \\sim C27A
\\sim C28A \\sim C29A \\sim C30A \\sim C31A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C22) = Uanis(C22A)
Uanis(O5) = Uanis(O5A)
Uanis(O3A) = Uanis(O3)
4. Rigid body (RIGU) restrains
 O2, O3, O4, O5, C22, C23, C24, C25, C26, C27, C28, C29, C30, C31, O2A, O3A,
 O4A, O5A, C22A, C23A, C24A, C25A, C26A, C27A, C28A, C29A, C30A, C31A
 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, C22, C23, C24, C25, C26, C27, C28, C29, C30, C31} sigma for
1-2: 0.01, 1-3: 0.04
as
{O2A, O3A, O4A, O5A, C22A, C23A, C24A, C25A, C26A, C27A, C28A, C29A, C30A, C31A}
6. 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)
7.a Riding coordinates:
 O3(H3a), O5(H5a), O3A(H3Aa), O5A(H5Aa)
7.b Ternary CH refined with riding coordinates:
 C23(H23), C25(H25), C27(H27), C31(H31), C23A(H23A), C25A(H25A), C27A(H27A),
 C31A(H31A)
7.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)
7.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C16(H16), C17(H17), C19(H19), C20(H20)
7.e Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C14(H14a,H14b,H14c), C21(H21a,H21b,H21c)
;
_shelx_res_checksum              41
_shelx_hkl_checksum              94516
_olex2_submission_special_instructions 'No special instructions were received'