Lactonization with concomitant 1,2-aryl migration and alkoxylation mediated by dialkoxyphenyl iodides generated <i>in situ</i>.
Zhang, Jingran; Jalil, Ayesha; He, Jiaxin; Yu, Zhenyang; Cheng, Yifu; Li, Guangchen; Du, Yunfei; Zhao, Kang; Chemical communications (Cambridge, England) 57 (2021) 7426–7429; doi:10.1039/d1cc03110d

data_7128564
_publ_section_title
;
 Lactonization with concomitant 1,2-aryl migration and alkoxylation
 mediated by dialkoxyphenyl iodides generated <i>in situ</i>.
;
_journal_issue                   60
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7426
_journal_page_last               7429
_journal_paper_doi               10.1039/d1cc03110d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C16 H14 O3'
_chemical_formula_sum            'C16 H14 O3'
_chemical_formula_weight         254.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-21
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.05.07 svn.rd67b107b for OlexSys, GUI svn.r6105)
;
_audit_update_record
;
2021-02-19 deposited with the CCDC.	2021-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.2470(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.74290(10)
_cell_length_b                   10.55120(10)
_cell_length_c                   14.69710(10)
_cell_measurement_reflns_used    28149
_cell_measurement_temperature    99.97(11)
_cell_measurement_theta_max      72.6730
_cell_measurement_theta_min      4.9180
_cell_volume                     2592.19(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (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      99.97(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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   -113.00 -32.00   0.50    0.05    --  -35.99 149.00-165.00  162
  2  \w   -111.00 -64.00   0.50    0.05    --  -35.99-149.00 147.00   94
  3  \w    -98.00 -19.00   0.50    0.05    --  -35.99 123.00  31.00  158
  4  \w     58.00 111.00   0.50    0.05    --   35.99 149.00-165.00  106
  5  \w     13.00  98.00   0.50    0.05    --   35.99-123.00 -49.00  170
  6  \w     26.00 113.00   0.50    0.05    --   35.99-149.00 147.00  174
  7  \w   -171.00 -63.00   0.50    0.20    -- -100.00-149.00 147.00  216
  8  \w   -177.00 -80.00   0.50    0.20    -- -100.00-123.00 -49.00  194
  9  \w   -134.00 -32.00   0.50    0.20    -- -100.00 149.00-165.00  204
 10  \w   -115.00 -19.00   0.50    0.20    -- -100.00 123.00  31.00  192
 11  \w     75.00 178.00   0.50    0.20    --  108.37 123.00  31.00  206
 12  \w     28.00 115.00   0.50    0.20    --  108.37-123.00 -49.00  174
 13  \w     33.00 133.00   0.50    0.20    --  108.37-149.00 147.00  200
 14  \w      6.00 113.00   0.50    0.05    --   35.99  57.00-180.00  214
 15  \w      6.00 113.00   0.50    0.05    --   35.99  57.00   0.00  214
 16  \w    -48.00  75.00   0.50    0.05    --   35.99 -37.00-180.00  246
 17  \w      6.00 113.00   0.50    0.05    --   35.99  57.00 120.00  214
 18  \w   -177.00 -86.00   0.50    0.20    -- -100.00-111.00-150.00  182
 19  \w   -177.00 -84.00   0.50    0.20    -- -100.00 -94.00-120.00  186
 20  \w   -111.00 -17.00   0.50    0.20    -- -100.00 111.00-150.00  188
 21  \w   -177.00 -84.00   0.50    0.20    -- -100.00 -94.00-180.00  186
 22  \w   -132.00 -24.00   0.50    0.20    -- -100.00  61.00-120.00  216
 23  \w   -177.00 -84.00   0.50    0.20    -- -100.00 -94.00  60.00  186
 24  \w     81.00 178.00   0.50    0.20    --  108.37 111.00 -30.00  194
 25  \w     77.00 178.00   0.50    0.20    --  108.37  61.00 -60.00  202
 26  \w     74.00 178.00   0.50    0.20    --  108.37  45.00-120.00  208
 27  \w     81.00 178.00   0.50    0.20    --  108.37 111.00-180.00  194
 28  \w     23.00 108.00   0.50    0.20    --  108.37 -94.00  30.00  170
 29  \w     26.00 112.00   0.50    0.20    --  108.37-111.00 150.00  172
 30  \w     23.00 108.00   0.50    0.20    --  108.37 -94.00  60.00  170
 31  \w     23.00 108.00   0.50    0.20    --  108.37 -94.00 150.00  170
 32  \w     23.00 108.00   0.50    0.20    --  108.37 -94.00 -90.00  170
 33  \w     27.00 143.00   0.50    0.20    --  108.37 -45.00 -90.00  232
 34  \w   -115.00   2.00   0.50    0.05    --  -35.99 -77.00 -30.00  234
 35  \w     39.00 124.00   0.50    0.05    --   35.99 179.00  90.00  170
 36  \w      6.00 113.00   0.50    0.05    --   35.99  57.00  30.00  214
 37  \w     -2.00 115.00   0.50    0.05    --   35.99  77.00-150.00  234
 38  \w     -2.00 115.00   0.50    0.05    --   35.99  77.00 -60.00  234
 39  \w     -2.00 115.00   0.50    0.05    --   35.99  77.00 150.00  234
 40  \w     -2.00 115.00   0.50    0.05    --   35.99  77.00  30.00  234
 41  \w      6.00 113.00   0.50    0.05    --   35.99  57.00 -90.00  214
 42  \w   -177.00 -62.00   0.50    0.20    -- -100.00 -77.00-150.00  230
 43  \w   -176.00 -68.00   0.50    0.20    -- -100.00 -61.00-150.00  216
 44  \w   -176.00 -68.00   0.50    0.20    -- -100.00 -61.00   0.00  216
 45  \w   -177.00 -62.00   0.50    0.20    -- -100.00 -77.00 -90.00  230
 46  \w   -176.00 -68.00   0.50    0.20    -- -100.00 -61.00-120.00  216
 47  \w   -177.00 -62.00   0.50    0.20    -- -100.00 -77.00 -30.00  230
 48  \w   -177.00 -62.00   0.50    0.20    -- -100.00 -77.00  60.00  230
 49  \w   -177.00 -65.00   0.50    0.20    -- -100.00 -45.00 150.00  224
 50  \w   -177.00 -62.00   0.50    0.20    -- -100.00 -77.00-120.00  230
 51  \w   -177.00 -62.00   0.50    0.20    -- -100.00 -77.00   0.00  230
 52  \w   -177.00 -62.00   0.50    0.20    -- -100.00 -77.00 -60.00  230
 53  \w   -177.00 -62.00   0.50    0.20    -- -100.00 -77.00 120.00  230
 54  \w   -177.00 -62.00   0.50    0.20    -- -100.00 -77.00-180.00  230
 55  \w   -176.00 -68.00   0.50    0.20    -- -100.00 -61.00 -30.00  216
 56  \w   -177.00 -62.00   0.50    0.20    -- -100.00 -77.00  30.00  230
 57  \w   -177.00 -51.00   0.50    0.20    -- -100.00 -30.00  60.00  252
 58  \w   -176.00 -68.00   0.50    0.20    -- -100.00 -61.00 -60.00  216
 59  \w   -176.00 -68.00   0.50    0.20    -- -100.00 -61.00  30.00  216
 60  \w   -177.00 -62.00   0.50    0.20    -- -100.00 -77.00  90.00  230
 61  \w   -176.00 -68.00   0.50    0.20    -- -100.00 -61.00  90.00  216
 62  \w   -176.00 -68.00   0.50    0.20    -- -100.00 -61.00 150.00  216
 63  \w   -176.00 -68.00   0.50    0.20    -- -100.00 -61.00  60.00  216
 64  \w   -177.00 -62.00   0.50    0.20    -- -100.00 -77.00 150.00  230
 65  \w     70.00 178.00   0.50    0.20    --  108.37  77.00 120.00  216
 66  \w   -125.00 -45.00   0.50    0.05    --  -35.99-179.00-150.00  160
 67  \w   -125.00 -45.00   0.50    0.05    --  -35.99-179.00   0.00  160
 68  \w      6.00 113.00   0.50    0.05    --   35.99  57.00  90.00  214
 69  \w     -3.00 120.00   0.50    0.05    --   35.99  37.00 -30.00  246
 70  \w      6.00 113.00   0.50    0.05    --   35.99  57.00-150.00  214
 71  \w     -2.00 115.00   0.50    0.05    --   35.99  77.00 -30.00  234
 72  \w     -3.00 120.00   0.50    0.05    --   35.99  37.00 -90.00  246
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0133314000
_diffrn_orient_matrix_UB_12      0.1437250000
_diffrn_orient_matrix_UB_13      0.0098106000
_diffrn_orient_matrix_UB_21      -0.0907009000
_diffrn_orient_matrix_UB_22      -0.0224316000
_diffrn_orient_matrix_UB_23      0.0033478000
_diffrn_orient_matrix_UB_31      0.0095053000
_diffrn_orient_matrix_UB_32      -0.0127261000
_diffrn_orient_matrix_UB_33      0.1044669000
_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  0.0393
_diffrn_reflns_av_unetI/netI     0.0105
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            45394
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.903
_diffrn_reflns_theta_min         4.957
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (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    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0403P)^2^+1.9252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2455
_reflns_number_total             2550
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03110d2.cif
_cod_data_source_block           034360_jiali3_100k_b
_cod_depositor_comments          'Adding full bibliography for 7128564.cif.'
_cod_database_code               7128564
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     'Ian '
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.899
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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:
 C7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c)
;
_shelx_res_checksum              35561
_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 1.913
_oxdiff_exptl_absorpt_empirical_full_min 0.808