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_7708497
_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         'C44 H34 O2 P2, C H2 Cl2'
_chemical_formula_sum            'C45 H36 Cl2 O2 P2'
_chemical_formula_weight         741.58
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-17 deposited with the CCDC.	2021-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                86.205(3)
_cell_angle_beta                 86.487(3)
_cell_angle_gamma                72.612(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0759(5)
_cell_length_b                   11.4561(7)
_cell_length_c                   20.3379(12)
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      26.713
_cell_measurement_theta_min      2.163
_cell_volume                     2011.7(2)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            54613
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         4.328
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1477 before and 0.0750 after correction. The Ratio of minimum to maximum transmission is 0.8330. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       block
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.514
_exptl_crystal_size_mid          0.367
_exptl_crystal_size_min          0.208
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         7046
_refine_ls_number_restraints     271
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0390P)^2^+1.6252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5696
_reflns_number_total             7046
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03243g2.cif
_cod_data_source_block           fa381
_cod_database_code               7708497
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.871
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 Cl2T-C3T \\sim Cl2S-C3S \\sim Cl1T-C3T \\sim Cl1S-C3S
 with sigma of 0.02
 Cl1S-Cl2S \\sim Cl1T-Cl2T
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C33 \\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C33A \\sim C34A
\\sim C35A \\sim C36A \\sim C37A \\sim C38A: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04
Uanis(C3S) = Uanis(C3T)
Uanis(Cl1S) = Uanis(Cl1T)
Uanis(Cl2S) = Uanis(Cl2T)
Uanis(C33) = Uanis(C33A)
4. Rigid body (RIGU) restrains
 C33, C34, C35, C36, C37, C38, C33A, C34A, C35A, C36A, C37A, C38A
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
5. Others
 Sof(Cl2T)=Sof(Cl1T)=Sof(C3T)=Sof(H3TA)=Sof(H3TB)=1-FVAR(1)
 Sof(Cl1S)=Sof(Cl2S)=Sof(C3S)=Sof(H3SA)=Sof(H3SB)=FVAR(1)
 Sof(C33A)=Sof(C34A)=Sof(H34A)=Sof(C35A)=Sof(H35A)=Sof(C36A)=Sof(H36A)=
 Sof(C37A)=Sof(H37A)=Sof(C38A)=Sof(H38A)=1-FVAR(2)
 Sof(C33)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=Sof(C36)=Sof(H36)=Sof(C37)=
 Sof(H37)=Sof(C38)=Sof(H38)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6)
6.b Secondary CH2 refined with riding coordinates:
 C3S(H3SA,H3SB), C3T(H3TA,H3TB)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34),
 C35(H35), C36(H36), C37(H37), C38(H38), C34A(H34A), C35A(H35A), C36A(H36A),
 C37A(H37A), C38A(H38A), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44)
6.d Fitted hexagon refined as free rotating group:
 C33(C34,C35,C36,C37,C38), C33A(C34A,C35A,C36A,C37A,C38A)
;
_shelx_res_checksum              22071
_shelx_hkl_checksum              54547
_shelx_fab_checksum              57109
_olex2_submission_special_instructions 'No special instructions were received'