Synthesis of dispiro-orthoester <i>via</i> an acetal oxo-carbenium ion.
Kumar, Manoj; Singh, Shubham; Subramanian, Parthasarathi; Chemical communications (Cambridge, England) 60 (2024) 12860–12863; doi:10.1039/d4cc03031a

data_7133659
_publ_section_title
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 Synthesis of dispiro-orthoester <i>via</i> an acetal oxo-carbenium ion.
;
_journal_issue                   88
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12860
_journal_page_last               12863
_journal_paper_doi               10.1039/d4cc03031a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C14 H16 O4'
_chemical_formula_sum            'C14 H16 O4'
_chemical_formula_weight         248.26
_chemical_name_systematic
3,3-dimethyl-1,5,7-trioxadispiro[5.1.58.26]pentadeca-9,12,14-trien-11-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-02-08 deposited with the CCDC.	2024-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 129.818(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.5396(8)
_cell_length_b                   5.76770(10)
_cell_length_c                   20.9082(6)
_cell_measurement_reflns_used    9172
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.43
_cell_measurement_theta_min      2.54
_cell_volume                     2550.85(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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  0.0516
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20942
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.575
_diffrn_reflns_theta_min         1.971
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5520
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1621 before and 0.0753 after correction.
The Ratio of minimum to maximum transmission is 0.7402.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1056
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.046
_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     165
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0428P)^2^+2.1382P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1036
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2686
_reflns_number_total             3226
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03031a2.cif
_cod_data_source_block           1maya_o
_cod_depositor_comments
;
Adding full bibliography for 7133655--7133659.cif.

2025-03-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C28 H32 O8'
_cod_original_formula_weight         496.53
_cod_original_formula_moiety         '2(C14 H16 O4)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        2550.85(13)
_cod_database_code               7133659
_shelx_shelxl_version_number     2019/3
_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
2.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00G(H00E,H00G)
2.b Aromatic/amide H refined with riding coordinates:
 C005(H005), C007(H007), C008(H008), C00B(H00C), C00C(H00D), C00F(H00F)
2.c Idealised Me refined as rotating group:
 C00H(H00H,H00I,H00J), C00I(H00K,H00L,H00M)
;
_shelx_res_checksum              84056
_shelx_hkl_checksum              97903
_olex2_submission_special_instructions 'No special instructions were received'