Enantioselective Synthesis of Cyclohexadienone Containing Spiroketals via DyKat Ketalization/oxa-Michael Addition Cascade.
Reddy, Reddy Rajasekhar; Panda, Shibaram; Ghorai, Prasanta; The Journal of organic chemistry 84 (2019) 5357–5368; doi:10.1021/acs.joc.9b00371

data_4034311
_publ_section_title
;
 Enantioselective Synthesis of Cyclohexadienone Containing Spiroketals via
 DyKat Ketalization/oxa-Michael Addition Cascade.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5357
_journal_page_last               5368
_journal_paper_doi               10.1021/acs.joc.9b00371
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration S
_chemical_formula_moiety         'C24 H19 I O4'
_chemical_formula_sum            'C24 H19 I O4'
_chemical_formula_weight         494.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-09-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8288(5)
_cell_length_b                   10.6374(8)
_cell_length_c                   29.5460(15)
_cell_measurement_reflns_used    3285
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      23.29
_cell_measurement_theta_min      2.82
_cell_volume                     2146.2(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_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  0.0639
_diffrn_reflns_av_unetI/netI     0.0916
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            8959
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.359
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.519
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0875 before and 0.0620 after correction.
The Ratio of minimum to maximum transmission is 0.8178.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 730 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0546P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1218
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                2340
_reflns_number_total             3635
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00371_si_002.cif
_cod_data_source_block           try2
_cod_depositor_comments
;

2020-10-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '0.13(C24 H19 I O4)'
_cod_original_formula_sum        'C3.10 H2.45 I0.13 O0.52'
_cod_original_formula_units_Z    31
_cod_original_formula_weight     64.30
_cod_database_code               4034311
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.842
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C00T) \\sim Ueq, Uanis(O00F) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.001
3.a Ternary CH refined with riding coordinates:
 C00D(H00D)
3.b Secondary CH2 refined with riding coordinates:
 C00H(H00B,H00E), C00J(H00F,H00H), C00T(H00J,H00M)
3.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00A(H00A), C00C(H00C), C00G(H00G), C00I(H00I),
 C00K(H00K), C00L(H00L), C00N(H00N), C00Q(H00Q), C00R(H00R), C00S(H00S)
;
_shelx_res_checksum              3734
_shelx_hkl_checksum              43153
_olex2_submission_special_instructions 'No special instructions were received'