Construction of 5-Methyleneoxazolidine-2,4-diones Bearing Modifiable Halogen Groups through a Halopalladation Strategy
Zhan, Huilin; Chen, Bin; Zhu, Biao; Li, Xiang; Han, Zhengyu; Sun, Jianwei; Huang, Hai; Chemical Communications  (2023) –; doi:10.1039/D3CC04475K

data_7132250
_publ_section_title
;
 Construction of 5-Methyleneoxazolidine-2,4-diones Bearing Modifiable
 Halogen Groups through a Halopalladation Strategy
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04475K
_journal_year                    2023
_chemical_formula_moiety         'C17 H12 Cl N O3'
_chemical_formula_sum            'C17 H12 Cl N O3'
_chemical_formula_weight         313.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-06-12
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-18 deposited with the CCDC.	2023-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.4445(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.33774(13)
_cell_length_b                   12.11111(16)
_cell_length_c                   12.88123(17)
_cell_measurement_reflns_used    6190
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.2080
_cell_measurement_theta_min      4.9170
_cell_volume                     1397.15(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_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     16.00 115.00   1.00    2.00    --   39.95  37.00 150.00   99
  2  \w    -20.00  74.00   1.00    2.00    --   39.95 -77.00-120.00   94
  3  \w    -30.00  62.00   1.00    2.00    --   39.95 -37.00 -30.00   92
  4  \w     80.00 178.00   1.00    3.50    --  107.44  30.00  60.00   98
  5  \w     37.00 137.00   1.00    3.50    --  107.44 -61.00 -30.00  100
  6  \w     77.00 176.00   1.00    3.50    --  107.44  30.00 150.00   99
  7  \w     24.00  66.00   1.00    3.50    --  107.44 -94.00 -60.00   42
  8  \w     63.00 146.00   1.00    3.50    --  107.44 178.00 -60.00   83
  9  \w     79.00 109.00   1.00    3.50    --  107.44-111.00  60.00   30
 10  \w     79.00 104.00   1.00    3.50    --  107.44 -94.00 -60.00   25
 11  \w     29.00 109.00   1.00    3.50    --  107.44-111.00 -90.00   80
 12  \w     61.00 138.00   1.00    3.50    --  107.44 -61.00  60.00   77
 13  \w    110.00 165.00   1.00    3.50    --  107.44 111.00  90.00   55
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0702944000
_diffrn_orient_matrix_UB_12      0.0254561000
_diffrn_orient_matrix_UB_13      -0.0920519000
_diffrn_orient_matrix_UB_21      -0.0813597000
_diffrn_orient_matrix_UB_22      0.1119933000
_diffrn_orient_matrix_UB_23      -0.0190784000
_diffrn_orient_matrix_UB_31      0.1342149000
_diffrn_orient_matrix_UB_32      0.0547267000
_diffrn_orient_matrix_UB_33      0.0819836000
_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  0.0162
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8023
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.102
_diffrn_reflns_theta_min         4.938
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.537
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.491
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0273
_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^)+(0.0397P)^2^+0.5699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2632
_reflns_number_total             2780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04475k2.cif
_cod_data_source_block           sliu11cult_auto
_cod_database_code               7132250
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C30 H28 Cl O N'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_shelx_res_checksum              19391
_shelx_hkl_checksum              69821
_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 1.524
_oxdiff_exptl_absorpt_empirical_full_min 0.604