Pd-Catalyzed carbonylative lactonization of 2-halidearomatic aldehydes with H<sub>2</sub>O as a nucleophile.
Si, Min; Yan, Jiaqi; Ding, Yongzheng; Huang, Hanmin; Organic & biomolecular chemistry 20 (2022) 3917–3921; doi:10.1039/d2ob00623e

data_7158669
_publ_section_title
;
 Pd-Catalyzed carbonylative lactonization of 2-halidearomatic aldehydes
 with H<sub>2</sub>O as a nucleophile.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3917
_journal_page_last               3921
_journal_paper_doi               10.1039/d2ob00623e
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C16 H10 O5'
_chemical_formula_sum            'C16 H10 O5'
_chemical_formula_weight         282.255
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_Int_Tables_number      15
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-04-02 deposited with the CCDC.	2022-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.503(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.3058(5)
_cell_length_b                   6.1080(2)
_cell_length_c                   28.2912(9)
_cell_measurement_reflns_used    2479
_cell_measurement_temperature    298
_cell_measurement_theta_max      72.4280
_cell_measurement_theta_min      5.8850
_cell_volume                     2591.76(15)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.9682
_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   -115.00 -25.00   1.00    2.00    --  -41.76 -38.00 -30.00   90
  2  \w    -36.00  -9.00   1.00    2.00    --  -41.76 116.00 127.00   27
  3  \w    -60.00  16.00   1.00    2.00    --  -41.76  38.00 -30.00   76
  4  \w     28.00  54.00   1.00    2.00    --   41.76  57.00 -90.00   26
  5  \w     25.00  51.00   1.00    4.00    --  106.05 -94.00 -30.00   26
  6  \w     56.00 105.00   1.00    4.00    --  106.05 -94.00 -30.00   49
  7  \w    133.00 170.00   1.00    4.00    --  106.05  77.00-180.00   37
  8  \w    130.00 166.00   1.00    4.00    --  106.05  77.00 150.00   36
  9  \w     82.00 171.00   1.00    4.00    --  106.05  61.00 -90.00   89
 10  \w     40.00 133.00   1.00    4.00    --  106.05 -61.00 120.00   93
 11  \w    147.00 178.00   1.00    4.00    --  106.05  77.00-150.00   31
 12  \w    113.00 168.00   1.00    4.00    --  106.05  77.00 120.00   55
;
_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      0.0894090000
_diffrn_orient_matrix_UB_12      -0.1237106000
_diffrn_orient_matrix_UB_13      0.0073639000
_diffrn_orient_matrix_UB_21      0.0017800000
_diffrn_orient_matrix_UB_22      -0.0140094000
_diffrn_orient_matrix_UB_23      0.0545511000
_diffrn_orient_matrix_UB_31      -0.0505372000
_diffrn_orient_matrix_UB_32      -0.2193584000
_diffrn_orient_matrix_UB_33      -0.0076140000
_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  0.0210
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.9974
_diffrn_reflns_Laue_measured_fraction_max 0.9682
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            4845
_diffrn_reflns_point_group_measured_fraction_full 0.9974
_diffrn_reflns_point_group_measured_fraction_max 0.9682
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         72.91
_diffrn_reflns_theta_min         5.90
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.915
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       needle
_exptl_crystal_F_000             1172.426
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.1726
_refine_diff_density_min         -0.2141
_refine_diff_density_rms         0.0461
_refine_ls_d_res_high            0.8065
_refine_ls_d_res_low             7.4992
_refine_ls_goodness_of_fit_ref   1.0486
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0486
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.8543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1044
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              0
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              32
_reflns_limit_l_min              -34
_reflns_number_gt                2152
_reflns_number_total             2523
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2ob00623e2.cif
_cod_data_source_block           SM-UP_auto
_cod_depositor_comments
'Adding full bibliography for 7158669--7158670.cif.'
_cod_original_sg_symbol_Hall     '-C 2yc (x+z,y,-x)'
_cod_database_code               7158669
_chemical_oxdiff_formula         C10H20O3
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C3(H3), C6(H6), C11(H11), C14(H14), C13(H13), C5(H5), C4(H4)
;
_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 1.274
_oxdiff_exptl_absorpt_empirical_full_min 0.692