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_4033847
_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_absolute_configuration ad
_chemical_formula_moiety         'C24 H22 O7'
_chemical_formula_sum            'C24 H22 O7'
_chemical_formula_weight         422.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.0881(2)
_cell_length_b                   7.88590(10)
_cell_length_c                   35.7414(4)
_cell_measurement_reflns_used    22806
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.2770
_cell_measurement_theta_min      2.4990
_cell_volume                     3970.77(9)
_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 0.981
_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    -70.00  25.00   0.50    0.10    --  -47.82  75.00 -55.00  190
  2  \w     73.00  98.00   0.50    0.10    --   47.82  75.00 -55.00   50
  3  \w     83.00 178.00   0.50    0.20    --  104.75  75.00 -55.00  190
  4  \w     49.00 127.00   0.50    0.20    --  104.75 -75.00 177.00  156
  5  \w     44.00  85.00   0.50    0.20    --  104.75 -94.00  30.00   82
  6  \w     32.00  83.00   0.50    0.20    --  104.75 -94.00   0.00  102
  7  \w    -24.00  66.00   0.50    0.10    --   47.82 -75.00 177.00  180
  8  \w    -59.00 -34.00   0.50    0.20    -- -102.00  75.00 -55.00   50
  9  \w   -136.00 -91.00   0.50    0.20    -- -102.00 -45.00  60.00   90
 10  \w   -116.00 -71.00   0.50    0.10    --  -47.82-125.00 -30.00   90
 11  \w    -97.00 -72.00   0.50    0.10    --  -47.82-125.00-120.00   50
 12  \w   -136.00 -93.00   0.50    0.20    -- -102.00 -30.00-120.00   86
 13  \w   -170.00 -90.00   0.50    0.20    -- -102.00 -45.00-150.00  160
 14  \w   -175.00 -91.00   0.50    0.20    -- -102.00 -61.00-120.00  168
 15  \w   -135.00-110.00   0.50    0.20    -- -102.00 -15.00  90.00   50
 16  \w   -154.00-128.00   0.50    0.20    -- -102.00 -75.00 177.00   52
 17  \w   -102.00 -71.00   0.50    0.10    --  -47.82 -75.00 177.00   62
 18  \w    -65.00 -39.00   0.50    0.20    -- -102.00  48.00 156.00   52
 19  \w     52.00  78.00   0.50    0.20    --  104.75 -94.00 -30.00   52
 20  \w     53.00  78.00   0.50    0.10    --   47.70  48.00 156.00   50
 21  \w    -97.00 -72.00   0.50    0.20    -- -102.00  48.00 156.00   50
;
_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      -0.0799009000
_diffrn_orient_matrix_UB_12      0.0078395000
_diffrn_orient_matrix_UB_13      0.0392619000
_diffrn_orient_matrix_UB_21      -0.1401955000
_diffrn_orient_matrix_UB_22      0.0645239000
_diffrn_orient_matrix_UB_23      -0.0158596000
_diffrn_orient_matrix_UB_31      -0.1100778000
_diffrn_orient_matrix_UB_32      -0.0878858000
_diffrn_orient_matrix_UB_33      -0.0081640000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            27953
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.563
_diffrn_reflns_theta_min         2.472
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37529
_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    1.413
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 3091 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.23(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         7424
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0406P)^2^+1.4267P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0786
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    0.882
_reflns_Friedel_fraction_max     0.818
_reflns_number_gt                7217
_reflns_number_total             7424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01677_si_006.cif
_cod_data_source_block           20190514a
_cod_original_cell_volume        3970.78(9)
_cod_database_code               4033847
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c1h1o1
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.781
_diffrn_oxdiff_digest_frames
;
016662a95573e15b2721e77db9610d387c018088bc2
;
_diffrn_oxdiff_digest_hkl
;
01f40f8aeef725008b1f26d4ff47689f85eebb
;
_reflns_odcompleteness_completeness 99.90
_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:
 C7(H7), C17(H17), C31(H31), C43(H43)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C26(H26), C27(H27), C28(H28), C29(H29), C38(H38), C39(H39), C40(H40), C41(H41)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C36(H36A,H36B,
 H36C), C46(H46A,H46B,H46C), C48(H48A,H48B,H48C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O10(H10)
;
_shelx_res_checksum              97854
_shelx_hkl_checksum              6714
_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 2.567
_oxdiff_exptl_absorpt_empirical_full_min 0.616