Construction of Complex Bisether-Bridged Medium-Sized Cyclic Compounds from <i>o</i>-(1-(Acyloxy)propargyl)benzaldehydes under Base and Acid Catalysis.
Zhao, Yun-Long; Cheng, Ying; The Journal of organic chemistry 84 (2019) 11114–11124; doi:10.1021/acs.joc.9b01677

data_4033846
_publ_section_title
;
 Construction of Complex Bisether-Bridged Medium-Sized Cyclic Compounds
 from <i>o</i>-(1-(Acyloxy)propargyl)benzaldehydes under Base and Acid
 Catalysis.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11114
_journal_page_last               11124
_journal_paper_doi               10.1021/acs.joc.9b01677
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C22 H18 O6'
_chemical_formula_sum            'C22 H18 O6'
_chemical_formula_weight         378.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.480(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.10270(10)
_cell_length_b                   27.9899(5)
_cell_length_c                   7.55070(10)
_cell_measurement_reflns_used    7041
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.9870
_cell_measurement_theta_min      3.1270
_cell_volume                     1678.19(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     51.00  76.00   0.50    0.10    --   47.82  64.00 -28.00   50
  2  \w    122.00 176.00   0.50    0.30    --  104.75  64.00 -28.00  108
  3  \w     97.00 178.00   0.50    0.30    --  104.75  61.00  30.00  162
  4  \w     40.00  80.00   0.50    0.30    --  104.75 -64.00-164.00   80
  5  \w     32.00 101.00   0.50    0.30    --  104.75 -94.00 -60.00  138
  6  \w     43.00 118.00   0.50    0.30    --  104.75 -30.00  30.00  150
  7  \w     37.00 108.00   0.50    0.30    --  104.75 -94.00  30.00  142
  8  \w    -23.00  58.00   0.50    0.10    --   47.82 -64.00-164.00  162
  9  \w    -63.00  25.00   0.50    0.10    --  -47.82  64.00 -28.00  176
 10  \w    -84.00 -59.00   0.50    0.30    -- -102.00  64.00 -28.00   50
 11  \w   -111.00 -53.00   0.50    0.10    --  -47.82 -64.00-164.00  116
 12  \w   -101.00 -74.00   0.50    0.10    --  -47.82-125.00 -60.00   54
 13  \w   -119.00 -73.00   0.50    0.10    --  -47.82-125.00 -30.00   92
 14  \w   -175.00-129.00   0.50    0.30    -- -102.00 -64.00-164.00   92
 15  \w   -175.00 -86.00   0.50    0.30    -- -102.00 -61.00 -90.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1274125000
_diffrn_orient_matrix_UB_12      0.0049006000
_diffrn_orient_matrix_UB_13      0.1799644000
_diffrn_orient_matrix_UB_21      0.0888036000
_diffrn_orient_matrix_UB_22      0.0408216000
_diffrn_orient_matrix_UB_23      -0.0809681000
_diffrn_orient_matrix_UB_31      -0.1162432000
_diffrn_orient_matrix_UB_32      0.0365779000
_diffrn_orient_matrix_UB_33      0.0664426000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10411
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.725
_diffrn_reflns_theta_min         3.158
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0352P)^2^+1.7064P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2984
_reflns_number_total             3318
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01677_si_005.cif
_cod_data_source_block           20190520c
_cod_database_code               4033846
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c1h1o1
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.899
_diffrn_oxdiff_digest_frames
;
0170ab4df898cd07bed0ab19a83c6b441c000508971
;
_diffrn_oxdiff_digest_hkl
;
019880d1aaa6df3459db134a00acd68a803342
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15)
2.d X=CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.f Idealised tetrahedral OH refined as rotating group:
 O5(H5A)
;
_shelx_res_checksum              45421
_shelx_hkl_checksum              2304
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.628
_oxdiff_exptl_absorpt_empirical_full_min 0.437