Regioselective Chlorolactonization of Styrene-Type Carboxylic Esters and Amides via PhICl<sub>2</sub>-Mediated Oxidative C-O/C-Cl Bond Formations.
Xing, Linlin; Zhang, Yong; Zhang, Yilin; Ai, Zhenkang; Li, Xuemin; Du, Yunfei; Deng, Jun; Zhao, Kang; The Journal of organic chemistry 84 (2019) 13832–13840; doi:10.1021/acs.joc.9b02022

data_4034574
_publ_section_title
;
 Regioselective Chlorolactonization of Styrene-Type Carboxylic Esters and
 Amides via PhICl<sub>2</sub>-Mediated Oxidative C-O/C-Cl Bond Formations.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13832
_journal_page_last               13840
_journal_paper_doi               10.1021/acs.joc.9b02022
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C16 H13 Cl N2 O4'
_chemical_formula_sum            'C16 H13 Cl N2 O4'
_chemical_formula_weight         332.73
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-05
_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            16
_cell_length_a                   16.2705(2)
_cell_length_b                   23.0829(3)
_cell_length_c                   16.4391(2)
_cell_measurement_reflns_used    8652
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.5820
_cell_measurement_theta_min      3.8340
_cell_volume                     6174.04(13)
_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 (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_type            HyPix
_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    -10.00  27.00   0.50    3.00    --  -46.12  57.00  60.00   74
  2  \w     57.00 110.00   0.50    3.00    --   46.12 163.00-102.00  106
  3  \w    -62.00 -14.00   0.50    3.00    --  -46.12  57.00  60.00   96
  4  \w    -97.00 -27.00   0.50    5.00    -- -100.00  45.00 150.00  140
  5  \w     32.00 108.00   0.50    3.00    --   46.12  57.00-150.00  152
  6  \w     33.00 113.00   0.50    5.00    --  101.75-117.00  20.00  160
  7  \w    105.00 130.00   0.50    5.00    --  101.75-143.00 -52.00   50
  8  \w     32.00  58.00   0.50    5.00    --  101.75-143.00 -52.00   52
  9  \w     41.00  98.00   0.50    5.00    --  101.75 -45.00 150.00  114
 10  \w   -175.00-100.00   0.50    5.00    -- -100.00 -12.00-179.00  150
;
_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      -0.0858101000
_diffrn_orient_matrix_UB_12      -0.0282380000
_diffrn_orient_matrix_UB_13      0.0007201000
_diffrn_orient_matrix_UB_21      0.0395076000
_diffrn_orient_matrix_UB_22      -0.0596287000
_diffrn_orient_matrix_UB_23      0.0152539000
_diffrn_orient_matrix_UB_31      -0.0059019000
_diffrn_orient_matrix_UB_32      0.0100170000
_diffrn_orient_matrix_UB_33      0.0925035000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22513
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.284
_diffrn_reflns_theta_min         3.323
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.397
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93556
_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    1.432
_exptl_crystal_description       plate
_exptl_crystal_F_000             2752
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.075
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         6064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0946P)^2^+4.2912P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1564
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4875
_reflns_number_total             6064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02022_si_002.cif
_cod_data_source_block           exp_60
_cod_database_code               4034574
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(O1A)=Sof(O7A)=1-FVAR(1)
 Sof(O1)=Sof(O7)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C23(H23), C24(H24), C7(H7), C8(H8)
3.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C27(H27), C29(H29),
 C30(H30), C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C13(H13), C14(H14)
3.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              1905
_shelx_hkl_checksum              83067
_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 1.099
_oxdiff_exptl_absorpt_empirical_full_min 0.883