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_4033843
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-18
_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                   20.3439(4)
_cell_length_b                   8.3230(2)
_cell_length_c                   22.9542(5)
_cell_measurement_reflns_used    7433
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3160
_cell_measurement_theta_min      3.8360
_cell_volume                     3886.66(15)
_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 0.961
_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    -59.00  -3.00   0.50    0.50    --  -47.70  37.00 131.00  112
  2  \w   -124.00 -82.00   0.50    2.00    -- -102.00-104.00-119.00   84
  3  \w     92.00 117.00   0.50    2.00    --  104.75  37.00 131.00   50
  4  \w     41.00 107.00   0.50    2.00    --  104.75 -93.00 138.00  132
  5  \w    -45.00   7.00   0.50    0.50    --  -47.70  37.00-180.00  104
  6  \w   -119.00 -72.00   0.50    0.50    --  -47.70-125.00 120.00   94
  7  \w     33.00  76.00   0.50    0.50    --   47.70  57.00-120.00   86
  8  \w    -83.00 -30.00   0.50    2.00    -- -102.00 125.00 -90.00  106
  9  \w     32.00 117.00   0.50    2.00    --  104.75 -37.00 -24.00  170
 10  \w     34.00 102.00   0.50    2.00    --  104.75-125.00-120.00  136
;
_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      0.0266774000
_diffrn_orient_matrix_UB_12      0.1652907000
_diffrn_orient_matrix_UB_13      -0.0187941000
_diffrn_orient_matrix_UB_21      -0.0678205000
_diffrn_orient_matrix_UB_22      0.0430925000
_diffrn_orient_matrix_UB_23      -0.0255218000
_diffrn_orient_matrix_UB_31      -0.0209063000
_diffrn_orient_matrix_UB_32      0.0707827000
_diffrn_orient_matrix_UB_33      0.0591497000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13714
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.593
_diffrn_reflns_theta_min         3.851
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86446
_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    1.382
_exptl_crystal_description       needle
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0410P)^2^+2.2473P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3482
_reflns_number_total             3887
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01677_si_002.cif
_cod_data_source_block           20190104a
_cod_database_code               4033843
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c1h1n1o1Cl1
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.791
_diffrn_oxdiff_digest_frames
;
0129558eba64f97d5753bad44d2041d791000454182
;
_diffrn_oxdiff_digest_hkl
;
010ca60687bfd4d2c11e563035a758337335ed
;
_reflns_odcompleteness_completeness 99.95
_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), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C15(H15), C16(H16), C17(H17), C18(H18)
2.d X=CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              20535
_shelx_hkl_checksum              7539
_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 2.407
_oxdiff_exptl_absorpt_empirical_full_min 0.590