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_7133658
_publ_section_title
;
 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         '0.167(C14 H16 O4)'
_chemical_formula_sum            'C2.33 H2.67 O0.67'
_chemical_formula_weight         41.38
_chemical_name_systematic
7,9,14-trioxadispiro[5.1.68.36]heptadeca-1,4,11-trien-3-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 92.5800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   6.61730(10)
_cell_length_b                   18.0893(4)
_cell_length_c                   10.0300(2)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      3.03
_cell_volume                     1199.40(4)
_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 0.996
_diffrn_measured_fraction_theta_max 0.997
_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  0.0643
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25099
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_min         2.324
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5174
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1481 before and 0.0709 after correction.
The Ratio of minimum to maximum transmission is 0.6938.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       irregular
_exptl_crystal_F_000             528
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0481P)^2^+0.4475P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2736
_reflns_number_total             2973
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03031a2.cif
_cod_data_source_block           24mayc_o_0m
_cod_depositor_comments
'Adding full bibliography for 7133655--7133659.cif.'
_cod_database_code               7133658
_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
2.a Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C008(H00C,H00D), C00A(H00E,H00F), C00C(H00H,H00I), C00D(H00J,
 H00K)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00G), C00E(H00L), C00F(H00M), C00G(H00N), C00H(H00O)
;
_shelx_res_checksum              11322
_shelx_hkl_checksum              34025
_olex2_submission_special_instructions 'No special instructions were received'