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_7133657
_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         '0.133(C14 H16 Br2 O4)'
_chemical_formula_sum            'C1.87 H2.13 Br0.27 O0.53'
_chemical_formula_weight         54.41
_chemical_name_systematic
3,3-bis(bromomethyl)-1,5,7-trioxadispiro[5.1.58.26]pentadeca-9,12-dien-11-one
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-02-05 deposited with the CCDC.	2024-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.2440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            30
_cell_length_a                   11.1660(3)
_cell_length_b                   10.3032(3)
_cell_length_c                   13.0230(3)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.53
_cell_volume                     1489.35(7)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24644
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.376
_diffrn_reflns_theta_min         2.526
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.452
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5224
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0805 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.7005.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_preparation       acetone
_exptl_crystal_recrystallization_method 'slow evaporation'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0194
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0151P)^2^+1.2115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0434
_refine_ls_wR_factor_ref         0.0443
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3421
_reflns_number_total             3720
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03031a2.cif
_cod_data_source_block           15sepa_o_0m
_cod_depositor_comments
'Adding full bibliography for 7133655--7133659.cif.'
_cod_database_code               7133657
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C00A(H00C,H00D), C00B(H00E,H00F), C00E(H00H,H00I), C00F(H00J,
 H00K), C00G(H00L,H00M)
1.b Aromatic/amide H refined with riding coordinates:
 C00D(H00G), C00H(H00N), C00J(H00O), C00K(H00P)
;
_shelx_res_checksum              45285
_shelx_hkl_checksum              26551
_olex2_submission_special_instructions 'No special instructions were received'