Design, synthesis, crystal structure, and herbicidal activity of novel pyrrolidine-2,4-dione derivatives incorporating an alkyl ether pharmacophore with natural tetramic acids as lead compounds
Chen, Min; Geng, Chun-Wen; Han, Ling; Liu, Yu; Yu, Yong-Kai; Lu, Ai-Min; Yang, Chun-Long; Li, Guo-Hua; New Journal of Chemistry 45 (2021) 5621–5630; doi:10.1039/D1NJ00119A

data_7060422
_publ_section_title
;
 Design, synthesis, crystal structure, and herbicidal activity of novel
 pyrrolidine-2,4-dione derivatives incorporating an alkyl ether
 pharmacophore with natural tetramic acids as lead compounds
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5621
_journal_page_last               5630
_journal_paper_doi               10.1039/D1NJ00119A
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C14 Cl N O4'
_chemical_formula_sum            'C14 Cl N O4'
_chemical_formula_weight         281.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2020-04-04 deposited with the CCDC.	2021-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                68.650(5)
_cell_angle_beta                 76.418(6)
_cell_angle_gamma                81.653(6)
_cell_formula_units_Z            4
_cell_length_a                   8.0403(7)
_cell_length_b                   13.5577(9)
_cell_length_c                   14.0775(7)
_cell_measurement_reflns_used    4371
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.0210
_cell_measurement_theta_min      3.4040
_cell_volume                     1386.26(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_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    -89.00  -7.00   1.00    1.00    --  -40.98 125.00 -90.00   82
  2  \w   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00   0.00   99
  3  \w    -93.00 -20.00   1.00    1.00    --  -40.98 -57.00-150.00   73
  4  \w     52.00  78.00   1.00    1.00    --   40.98-125.00-180.00   26
  5  \w     91.00 118.00   1.00    1.00    --  106.95-125.00-120.00   27
  6  \w     48.00 130.00   1.00    1.00    --  106.95 -45.00 -90.00   82
  7  \w     89.00 178.00   1.00    1.00    --  106.95  30.00 -30.00   89
  8  \w    150.00 177.00   1.00    1.00    --  106.95 125.00-120.00   27
  9  \w    127.00 173.00   1.00    1.00    --  106.95 125.00 -60.00   46
 10  \w     95.00 150.00   1.00    1.00    --  106.95 125.00 -30.00   55
 11  \w     98.00 125.00   1.00    1.00    --  106.95 125.00-120.00   27
 12  \w     95.00 173.00   1.00    1.00    --  106.95 125.00   0.00   78
 13  \w    106.00 132.00   1.00    1.00    --  106.95 125.00 150.00   26
 14  \w     83.00 164.00   1.00    1.00    --  106.95  61.00  60.00   81
 15  \w     55.00 109.00   1.00    1.00    --  106.95 -95.00  30.00   54
 16  \w     43.00 129.00   1.00    1.00    --  106.95 -45.00  30.00   86
 17  \w     35.00 103.00   1.00    1.00    --  106.95 -95.00 -60.00   68
 18  \w   -111.00 -20.00   1.00    1.00    --  -40.98 -57.00 120.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0585722000
_diffrn_orient_matrix_UB_12      0.1182465000
_diffrn_orient_matrix_UB_13      -0.0447364000
_diffrn_orient_matrix_UB_21      0.1857301000
_diffrn_orient_matrix_UB_22      0.0301122000
_diffrn_orient_matrix_UB_23      -0.0197645000
_diffrn_orient_matrix_UB_31      0.0331238000
_diffrn_orient_matrix_UB_32      -0.0078277000
_diffrn_orient_matrix_UB_33      -0.1094260000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9377
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.813
_diffrn_reflns_theta_min         3.439
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.238
_exptl_crystal_description       block
_exptl_crystal_F_000             546
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.0020(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0770
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1771P)^2^+0.4655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2478
_refine_ls_wR_factor_ref         0.2684
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4286
_reflns_number_total             5385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj00119a2.cif
_cod_data_source_block           nl1209-2
_cod_depositor_comments
;
          Adding full bibliography for 7060422.cif.

2025-03-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C11 H10 Cl0 N O'
_cod_original_formula_weight         172.20
_cod_original_formula_moiety         '0.67(C14 Cl N O4)'
_cod_original_formula_units_Z            6
_cod_database_code               7060422
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_res_checksum              99237
_shelx_hkl_checksum              16552
_olex2_date_sample_data_collection 2019-12-09
_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 1.915
_oxdiff_exptl_absorpt_empirical_full_min 0.604