Tandem Rh(ii)-catalyzed 1,3-acyloxy migration/intermolecular [2 + 2] cycloaddition of electron-deficient propargylic esters with alkenes and alkynes.
Xu, Zurong; Zhu, Dong; Wu, Rui; Zhu, Shifa; Chemical science 16 (2024) 205–210; doi:10.1039/d4sc06458e

data_1573215
_publ_section_title
;
 Tandem Rh(ii)-catalyzed 1,3-acyloxy migration/intermolecular [2 + 2]
 cycloaddition of electron-deficient propargylic esters with alkenes and
 alkynes.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              205
_journal_page_last               210
_journal_paper_doi               10.1039/d4sc06458e
_journal_volume                  16
_journal_year                    2024
_chemical_formula_moiety         'C16 H14 O5'
_chemical_formula_sum            'C16 H14 O5'
_chemical_formula_weight         286.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-02-27 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.683(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.7856(4)
_cell_length_b                   6.0442(4)
_cell_length_c                   16.6292(9)
_cell_measurement_reflns_used    2083
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.3590
_cell_measurement_theta_min      5.3060
_cell_volume                     681.27(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.962
_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     -2.00  61.00   1.00    1.00    --   40.73 -57.00   0.00   63
  2  \w     31.00 134.00   1.00    1.00    --  106.95 -30.00 -90.00  103
  3  \w     93.00 119.00   1.00    1.00    --  106.95-125.00-180.00   26
  4  \w     54.00  80.00   1.00    1.00    --  106.95-125.00-180.00   26
  5  \w     26.00 101.00   1.00    1.00    --  106.95 -95.00  90.00   75
  6  \w     86.00 111.00   1.00    1.00    --  106.95  45.00  90.00   25
  7  \w    132.00 164.00   1.00    1.00    --  106.95  45.00  90.00   32
  8  \w    115.00 177.00   1.00    1.00    --  106.95 125.00  60.00   62
  9  \w     94.00 170.00   1.00    1.00    --  106.95 125.00   0.00   76
 10  \w    -34.00   3.00   1.00    1.00    --   40.73 -77.00 150.00   37
 11  \w    -67.00  31.00   1.00    1.00    --  -40.73  57.00-120.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0012453000
_diffrn_orient_matrix_UB_12      0.2295785000
_diffrn_orient_matrix_UB_13      0.0402826000
_diffrn_orient_matrix_UB_21      0.0244265000
_diffrn_orient_matrix_UB_22      -0.1101374000
_diffrn_orient_matrix_UB_23      0.0833625000
_diffrn_orient_matrix_UB_31      0.2260592000
_diffrn_orient_matrix_UB_32      0.0107062000
_diffrn_orient_matrix_UB_33      -0.0048817000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2502
_diffrn_reflns_point_group_measured_fraction_full 0.727
_diffrn_reflns_point_group_measured_fraction_max 0.688
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.435
_diffrn_reflns_theta_min         2.660
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.871
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details
;
 Flack x determined using 415 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       0.0157(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         1897
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0834
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0728P)^2^+3.7566P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2455
_refine_ls_wR_factor_ref         0.2464
_reflns_Friedel_coverage         0.302
_reflns_Friedel_fraction_full    0.393
_reflns_Friedel_fraction_max     0.355
_reflns_number_gt                1864
_reflns_number_total             1897
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06458e2.cif
_cod_data_source_block           179-4
_cod_depositor_comments
'Adding full bibliography for 1573214--1573215.cif.'
_cod_database_code               1573215
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.78
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C12(H12)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              21673
_shelx_hkl_checksum              39389
_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 1.502
_oxdiff_exptl_absorpt_empirical_full_min 0.480