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_7158670
_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_absolute_configuration unk
_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           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_Int_Tables_number      7
_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                 91.313(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.4392(1)
_cell_length_b                   6.5027(1)
_cell_length_c                   22.2547(3)
_cell_measurement_reflns_used    7546
_cell_measurement_temperature    298
_cell_measurement_theta_max      72.9140
_cell_measurement_theta_min      6.0600
_cell_volume                     642.25(2)
_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 1.0000
_diffrn_measured_fraction_theta_max 0.9915
_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    -35.00  30.00   1.00    2.00    --  -41.76  57.00  90.00   65
  2  \w   -114.00 -40.00   1.00    2.00    --  -41.76 -57.00  30.00   74
  3  \w    -64.00  31.00   1.00    2.00    --  -41.76  57.00  30.00   95
  4  \w    -65.00 -40.00   1.00    2.00    --  -41.76  57.00  90.00   25
  5  \w    -12.00  70.00   1.00    2.00    --   41.76 -57.00-150.00   82
  6  \w     39.00  73.00   1.00    4.00    --  106.05-125.00   0.00   34
  7  \w     34.00  59.00   1.00    4.00    --  106.05-125.00  90.00   25
  8  \w     39.00  74.00   1.00    4.00    --  106.05 -94.00 -90.00   35
  9  \w     55.00 134.00   1.00    4.00    --  106.05 -30.00 -60.00   79
 10  \w     52.00 132.00   1.00    4.00    --  106.05 -77.00  30.00   80
 11  \w     78.00 177.00   1.00    4.00    --  106.05  61.00 -60.00   99
 12  \w     34.00  92.00   1.00    4.00    --  106.05-118.00-128.00   58
 13  \w     86.00 112.00   1.00    4.00    --  106.05-125.00  90.00   26
 14  \w    143.00 174.00   1.00    4.00    --  106.05  77.00-120.00   31
 15  \w     85.00 126.00   1.00    4.00    --  106.05-142.00-117.23   41
 16  \w     82.00 109.00   1.00    4.00    --  106.05-114.00 -40.00   27
 17  \w     27.00 107.00   1.00    4.00    --  106.05 -94.00   0.00   80
 18  \w     23.00 161.00   1.00    4.00    --  106.05   0.00-180.00  138
 19  \w    -20.00   5.00   1.00    2.00    --   42.01 -77.00-120.00   25
 20  \w    108.00 134.00   1.00    4.00    --  106.05  77.00-180.00   26
 21  \w   -118.00 -54.00   1.00    2.00    --  -42.01-159.00  78.00   64
 22  \w   -114.00 -14.00   1.00    2.00    --  -42.01 -57.00-150.00  100
 23  \w   -114.00 -14.00   1.00    2.00    --  -42.01 -57.00 -60.00  100
 24  \w   -114.00 -14.00   1.00    2.00    --  -42.01 -57.00  60.00  100
 25  \w   -114.00 -14.00   1.00    2.00    --  -42.01 -57.00 150.00  100
 26  \w     78.00 178.00   1.00    4.00    --  106.05  30.00-120.00  100
 27  \w     80.00 178.00   1.00    4.00    --  106.05  45.00 120.00   98
 28  \w     77.00 178.00   1.00    4.00    --  106.05  61.00   0.00  101
 29  \w     77.00 178.00   1.00    4.00    --  106.05  61.00  30.00  101
 30  \w     77.00 178.00   1.00    4.00    --  106.05  61.00 150.00  101
 31  \w     77.00 178.00   1.00    4.00    --  106.05  61.00 -90.00  101
 32  \w     77.00 178.00   1.00    4.00    --  106.05  61.00-180.00  101
 33  \w     77.00 178.00   1.00    4.00    --  106.05  61.00  60.00  101
;
_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      0.0634559000
_diffrn_orient_matrix_UB_12      -0.2324350000
_diffrn_orient_matrix_UB_13      0.0049446000
_diffrn_orient_matrix_UB_21      -0.0498449000
_diffrn_orient_matrix_UB_22      -0.0223287000
_diffrn_orient_matrix_UB_23      -0.0684185000
_diffrn_orient_matrix_UB_31      0.3376189000
_diffrn_orient_matrix_UB_32      0.0401312000
_diffrn_orient_matrix_UB_33      -0.0093948000
_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  0.0175
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9915
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8918
_diffrn_reflns_point_group_measured_fraction_full 0.9177
_diffrn_reflns_point_group_measured_fraction_max 0.9002
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         73.00
_diffrn_reflns_theta_min         3.97
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79163
_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    1.460
_exptl_crystal_description       block
_exptl_crystal_F_000             293.107
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.1000
_refine_diff_density_min         -0.1573
_refine_diff_density_rms         0.0300
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.35(13)
_refine_ls_d_res_high            0.8061
_refine_ls_d_res_low             11.1244
_refine_ls_goodness_of_fit_ref   1.1546
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.1546
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.0393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0747
_reflns_Friedel_coverage         0.808
_reflns_limit_h_max              5
_reflns_limit_h_min              -4
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              27
_reflns_limit_l_min              -27
_reflns_number_gt                2308
_reflns_number_total             2317
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2ob00623e2.cif
_cod_data_source_block           SM-DOWN_auto
_cod_depositor_comments
'Adding full bibliography for 7158669--7158670.cif.'
_cod_original_sg_symbol_Hall     ' P -2yc (x-z,y,z)'
_cod_database_code               7158670
_chemical_oxdiff_formula         C20H20N2O2
_reflns_odcompleteness_completeness 99.92
_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:
 C8(H8), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C6(H6), C5(H5), C11(H11), C3(H3), C14(H14), C12(H12), 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 1.289
_oxdiff_exptl_absorpt_empirical_full_min 0.718