Electrophilic Cyclization and Intermolecular Acetalation of 2-(4-Hydroxybut-1-yn-1-yl)benzaldehydes: Synthesis of Diiodinated Diepoxydibenzo[c,k][1,9]dioxacyclohexadecines.
Wang, Jia; Zhu, Hai-Tao; Chen, Si; Luan, Cheng; Xia, Yu; Shen, Yi; Li, Ying-Xiu; Hua, Yingxi; Liang, Yong-Min; The Journal of organic chemistry 82 (2017) 10641–10649; doi:10.1021/acs.joc.7b01646

data_4032775
_publ_section_title
;
 Electrophilic Cyclization and Intermolecular Acetalation of
 2-(4-Hydroxybut-1-yn-1-yl)benzaldehydes: Synthesis of Diiodinated
 Diepoxydibenzo[c,k][1,9]dioxacyclohexadecines.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10641
_journal_page_last               10649
_journal_paper_doi               10.1021/acs.joc.7b01646
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C34 H24 Br2 I2 O4'
_chemical_formula_sum            'C34 H24 Br2 I2 O4'
_chemical_formula_weight         910.15
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.066(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4274(7)
_cell_length_b                   13.8870(6)
_cell_length_c                   16.6402(9)
_cell_measurement_reflns_used    2079
_cell_measurement_temperature    296.0(3)
_cell_measurement_theta_max      23.7470
_cell_measurement_theta_min      3.7010
_cell_volume                     3151.0(3)
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.0(3)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -14.00   24.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  -60.0000 38

  2 omega   61.00  102.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000   30.0000 41

  3 omega  -42.00   79.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000   30.0000 121

  4 omega   59.00  105.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867 -178.0000 -120.0000 46
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0101495000
_diffrn_orient_matrix_UB_12      -0.0118569000
_diffrn_orient_matrix_UB_13      0.0377988000
_diffrn_orient_matrix_UB_21      0.0025524000
_diffrn_orient_matrix_UB_22      -0.0496353000
_diffrn_orient_matrix_UB_23      -0.0088437000
_diffrn_orient_matrix_UB_31      0.0509638000
_diffrn_orient_matrix_UB_32      0.0001395000
_diffrn_orient_matrix_UB_33      0.0230121000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12569
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.29
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.569
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70500
_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_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.805
_refine_diff_density_min         -1.346
_refine_diff_density_rms         0.109
_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     379
_refine_ls_number_reflns         6199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0631
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+4.6343P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1743
_reflns_number_gt                3382
_reflns_number_total             6199
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01646_si_002.cif
_cod_data_source_block           wangjia_0508_2h
_cod_depositor_comments
'Adding full bibliography for 4032774--4032777.cif.'
_cod_database_code               4032775
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C26(H26), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C15(H15), C16(H16),
 C21(H21), C22(H22), C23(H23), C24(H24), C29(H29), C30(H30), C32(H32), C33(H33)
;
_olex2_date_sample_data_collection 2017-05-09
_olex2_submission_special_instructions 'No special instructions were received'