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_4033844
_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 O5'
_chemical_formula_sum            'C22 H18 O5'
_chemical_formula_weight         362.36
_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             2019-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.205(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8387(4)
_cell_length_b                   6.7800(2)
_cell_length_c                   15.4079(4)
_cell_measurement_reflns_used    6206
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3020
_cell_measurement_theta_min      2.7060
_cell_volume                     1689.18(8)
_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 0.999
_diffrn_measured_fraction_theta_max 0.964
_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    -23.00  56.00   0.50    0.06    --   47.70 -55.00  90.00  158
  2  \w     34.00  66.00   0.50    0.25    --  104.75 -55.00  90.00   64
  3  \w     15.00  92.00   0.50    0.06    --   47.70-125.00 -60.00  154
  4  \w     91.00 117.00   0.50    0.25    --  104.75 -45.00-150.00   52
  5  \w    106.00 177.00   0.50    0.25    --  104.75  15.00-180.00  142
  6  \w    109.00 134.00   0.50    0.25    --  104.75  55.00-125.00   50
  7  \w     92.00 177.00   0.50    0.25    --  104.75  45.00 -90.00  170
  8  \w     84.00 109.00   0.50    0.25    --  104.75 -94.00 -60.00   50
  9  \w     49.00  78.00   0.50    0.25    --  104.75 -45.00-150.00   58
 10  \w     34.00  70.00   0.50    0.25    --  104.75 -94.00 -60.00   72
 11  \w     33.00  78.00   0.50    0.06    --   47.70  55.00-125.00   90
 12  \w    -29.00  -3.00   0.50    0.06    --  -47.70  55.00-125.00   52
 13  \w    -61.00 -36.00   0.50    0.06    --  -47.70  55.00-125.00   50
 14  \w   -105.00 -29.00   0.50    0.25    -- -102.00  55.00-125.00  152
 15  \w   -109.00 -27.00   0.50    0.25    -- -102.00  15.00  60.00  164
 16  \w   -104.00 -52.00   0.50    0.25    -- -102.00  45.00  90.00  104
 17  \w   -118.00 -43.00   0.50    0.06    --  -47.70 -55.00  90.00  150
 18  \w   -171.00 -87.00   0.50    0.25    -- -102.00 -55.00  90.00  168
;
_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      0.0128035000
_diffrn_orient_matrix_UB_12      0.1436425000
_diffrn_orient_matrix_UB_13      0.0801783000
_diffrn_orient_matrix_UB_21      0.0933249000
_diffrn_orient_matrix_UB_22      -0.0462361000
_diffrn_orient_matrix_UB_23      0.0279321000
_diffrn_orient_matrix_UB_31      0.0143395000
_diffrn_orient_matrix_UB_32      0.1698077000
_diffrn_orient_matrix_UB_33      -0.0602937000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11399
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.457
_diffrn_reflns_theta_min         2.733
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52521
_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    1.425
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0594P)^2^+1.1308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1291
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2947
_reflns_number_total             3382
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01677_si_004.cif
_cod_data_source_block           20190305a
_cod_original_cell_volume        1689.17(8)
_cod_database_code               4033844
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c1h1n1o1
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.789
_diffrn_oxdiff_digest_frames
;
01cc1e1ab6abe6c9ed986b830428a898b4001260e46
;
_diffrn_oxdiff_digest_hkl
;
01bf56e75365af239e78dd67bf1588765e6555
;
_reflns_odcompleteness_completeness 100.00
_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:
 C8(H8), C10(H10), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
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)
2.d X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              8758
_shelx_hkl_checksum              48164
_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 1.676
_oxdiff_exptl_absorpt_empirical_full_min 0.449