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_4033845
_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         'C24 H20 O6'
_chemical_formula_sum            'C24 H20 O6'
_chemical_formula_weight         404.40
_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
_audit_creation_date             2018-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.140(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.7497(5)
_cell_length_b                   9.0408(2)
_cell_length_c                   10.2972(3)
_cell_measurement_reflns_used    4682
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.7710
_cell_measurement_theta_min      4.2950
_cell_volume                     1907.17(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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    -65.00  28.00   1.00    1.00    --  -41.49  57.00 -30.00   93
  2  \w   -116.00 -24.00   1.00    1.00    --  -41.49 -37.00-180.00   92
  3  \w   -105.00 -78.00   1.00    1.00    --  -41.49-146.00 -92.00   27
  4  \w    -92.00 -43.00   1.00    1.00    --  -41.49 125.00  60.00   49
  5  \w   -115.00 -29.00   1.00    1.00    --  -41.49 -37.00  90.00   86
  6  \w     57.00  84.00   1.00    1.00    --   41.49-125.00-180.00   27
  7  \w     32.00 118.00   1.00    3.00    --  104.69-125.00 -30.00   86
  8  \w     44.00 116.00   1.00    3.00    --  104.69 -45.00 -60.00   72
  9  \w     59.00 136.00   1.00    3.00    --  104.69 -77.00 -60.00   77
 10  \w     33.00 131.00   1.00    3.00    --  104.69 -45.00  30.00   98
 11  \w     35.00  80.00   1.00    3.00    --  104.69 -61.00 150.00   45
 12  \w     24.00  83.00   1.00    3.00    --  104.69 -94.00-120.00   59
 13  \w     71.00 109.00   1.00    3.00    --  104.69 -94.00  60.00   38
 14  \w     22.00  50.00   1.00    3.00    --  104.69 -94.00 -90.00   28
 15  \w    106.00 178.00   1.00    3.00    --  104.69  77.00  90.00   72
 16  \w     55.00 107.00   1.00    3.00    --  104.69 -94.00 150.00   52
 17  \w     19.00 169.00   1.00    3.00    --  104.69   0.00 -90.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0298662000
_diffrn_orient_matrix_UB_12      -0.1382818000
_diffrn_orient_matrix_UB_13      -0.0548578000
_diffrn_orient_matrix_UB_21      -0.0687791000
_diffrn_orient_matrix_UB_22      -0.0529160000
_diffrn_orient_matrix_UB_23      -0.0605200000
_diffrn_orient_matrix_UB_31      0.0056024000
_diffrn_orient_matrix_UB_32      0.0843929000
_diffrn_orient_matrix_UB_33      -0.1276264000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12879
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.906
_diffrn_reflns_theta_min         4.316
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (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    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0475P)^2^+0.7620P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3118
_reflns_number_total             3699
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01677_si_003.cif
_cod_data_source_block           20181018a
_cod_database_code               4033845
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c1h1o1
_shelx_estimated_absorpt_t_max   0.885
_shelx_estimated_absorpt_t_min   0.850
_reflns_odcompleteness_completeness 99.97
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              2492
_shelx_hkl_checksum              52421
_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 1.527
_oxdiff_exptl_absorpt_empirical_full_min 0.778