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_7133655
_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         'C13 H14 O4'
_chemical_formula_sum            'C13 H14 O4'
_chemical_formula_weight         234.24
_chemical_name_systematic        Manoj
_chemical_properties_physical    'Heat-sensitive,Acid senstive'
_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             2023-08-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-12 deposited with the CCDC.	2024-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.0640(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6135(4)
_cell_length_b                   5.8166(2)
_cell_length_c                   16.6086(5)
_cell_measurement_reflns_used    8183
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.18
_cell_volume                     1121.20(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14371
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_min         2.177
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6519
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1259 before and 0.0584 after correction.
The Ratio of minimum to maximum transmission is 0.8742.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_preparation       Acetone
_exptl_crystal_recrystallization_method 'Slow evporation'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.6729P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1790
_reflns_number_total             2065
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03031a2.cif
_cod_data_source_block           10feba_o_0m
_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            'C26 H28 O8'
_cod_original_formula_weight         468.48
_cod_original_formula_moiety         '2(C13 H14 O4)'
_cod_original_formula_units_Z            2
_cod_database_code               7133655
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.978
_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), C00B(H00D,H00E), C00C(H00F,H00G), C00D(H00H,H00I)
2.b Aromatic/amide H refined with riding coordinates:
 C005(H005), C008(H008), C00A(H00C), C00E(H00J), C00G(H00K), C00H(H00L)
;
_shelx_res_checksum              38902
_shelx_hkl_checksum              69242
_olex2_exptl_crystal_mounting_method 'Low temprature '
_olex2_submission_original_sample_id 'Manoj 6-5-7'
_olex2_submission_special_instructions 'No special instructions were received'