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_4032774
_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         'C22 H18 I2 O4'
_chemical_formula_sum            'C22 H18 I2 O4'
_chemical_formula_weight         600.16
_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
_audit_creation_date             2016-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.21(2)
_cell_angle_gamma                90
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_cell_length_a                   13.946(2)
_cell_length_b                   9.9498(9)
_cell_length_c                   14.897(2)
_cell_measurement_reflns_used    1605
_cell_measurement_temperature    295.15(10)
_cell_measurement_theta_max      25.6350
_cell_measurement_theta_min      3.8630
_cell_volume                     2050.8(5)
_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
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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      295.15(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9953
_diffrn_measured_fraction_theta_max 0.8815
_diffrn_measurement_details
;
  1 omega  -12.00   22.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000   90.0000 34

  2 omega  -47.00   43.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000 -120.0000 90

  3 omega  -47.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -38.0000  150.0000 94
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0047285000
_diffrn_orient_matrix_UB_12      0.0140490000
_diffrn_orient_matrix_UB_13      -0.0458817000
_diffrn_orient_matrix_UB_21      0.0434509000
_diffrn_orient_matrix_UB_22      -0.0379357000
_diffrn_orient_matrix_UB_23      0.0033402000
_diffrn_orient_matrix_UB_31      -0.0270033000
_diffrn_orient_matrix_UB_32      -0.0585766000
_diffrn_orient_matrix_UB_33      -0.0133945000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7189
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.434
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48651
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.944
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.933
_refine_diff_density_min         -1.491
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+2.0135P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2979
_reflns_number_total             4026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01646_si_002.cif
_cod_data_source_block           wangjia_1205_2a
_cod_depositor_comments
'Adding full bibliography for 4032774--4032777.cif.'
_cod_original_cell_volume        2050.7(5)
_cod_database_code               4032774
_chemical_oxdiff_formula         'CH N O'
_reflns_odcompleteness_completeness 99.53
_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:
 C8(H8), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-12-05
_olex2_submission_special_instructions 'No special instructions were received'