Facile Synthesis of Halogenated Spiroketals via a Tandem Iodocyclization.
Wang, Jia; Zhu, Hai-Tao; Li, Ying-Xiu; Wang, Li-Jing; Qiu, Yi-Feng; Qiu, Zi-Hang; Zhong, Mei-Jin; Liu, Xue-Yuan; Liang, Yong-Min; Organic letters 16 (2014) 2236–2239; doi:10.1021/ol500741a

data_1514254
_publ_section_title
;
 Facile Synthesis of Halogenated Spiroketals via a Tandem Iodocyclization.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2236
_journal_page_last               2239
_journal_paper_doi               10.1021/ol500741a
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C21 H17 Cl I2 O3'
_chemical_formula_sum            'C21 H17 Cl I2 O3'
_chemical_formula_weight         606.60
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4715)
;
_cell_angle_alpha                73.782(10)
_cell_angle_beta                 80.037(9)
_cell_angle_gamma                62.461(12)
_cell_formula_units_Z            2
_cell_length_a                   9.6504(11)
_cell_length_b                   10.0633(12)
_cell_length_c                   12.6865(12)
_cell_measurement_reflns_used    3517
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3760
_cell_measurement_theta_min      3.1860
_cell_volume                     1047.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.8841
_diffrn_measurement_details
;
  1 omega  -16.00   26.00   1.2000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -99.0000 -120.0000 35

  2 omega  -33.00   27.00   1.2000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262   57.0000 -120.0000 50

  3 omega  -50.00   92.80   1.2000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       22.8075    0.0000   30.0000 119

  4 omega   57.00  105.00   1.2000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  178.0000 -120.0000 40

  5 omega   -2.00   36.40   1.2000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   57.0000  120.0000 32

  6 omega  -12.00   48.00   1.2000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -57.0000  -30.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0751464000
_diffrn_orient_matrix_UB_12      -0.0599773000
_diffrn_orient_matrix_UB_13      0.0144075000
_diffrn_orient_matrix_UB_21      -0.0182436000
_diffrn_orient_matrix_UB_22      -0.0517459000
_diffrn_orient_matrix_UB_23      -0.0163677000
_diffrn_orient_matrix_UB_31      0.0301564000
_diffrn_orient_matrix_UB_32      0.0197735000
_diffrn_orient_matrix_UB_33      -0.0540736000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6749
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.98
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.148
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.923
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_refine_diff_density_max         1.043
_refine_diff_density_min         -1.671
_refine_diff_density_rms         0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0317P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                3023
_reflns_number_total             4122
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol500741a_si_001.cif
_cod_data_source_block           wangjia1121
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-8800/cifs/1514254.cif.
;
_cod_database_code               1514254
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C16(H16), C17(H17), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;