#------------------------------------------------------------------------------
#$Date: 2025-03-07 17:30:27 +0100 (Fri 07 de Mar de 2025) $
#$Revision: 298328 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/04/7060422.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7060422
loop_
_publ_author_name
'Chen, Min'
'Geng, Chun-Wen'
'Han, Ling'
'Liu, Yu'
'Yu, Yong-Kai'
'Lu, Ai-Min'
'Yang, Chun-Long'
'Li, Guo-Hua'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  -7.00   1.00    1.00    --  -40.98 125.00 -90.00   82
  2  ω   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00   0.00   99
  3  ω    -93.00 -20.00   1.00    1.00    --  -40.98 -57.00-150.00   73
  4  ω     52.00  78.00   1.00    1.00    --   40.98-125.00-180.00   26
  5  ω     91.00 118.00   1.00    1.00    --  106.95-125.00-120.00   27
  6  ω     48.00 130.00   1.00    1.00    --  106.95 -45.00 -90.00   82
  7  ω     89.00 178.00   1.00    1.00    --  106.95  30.00 -30.00   89
  8  ω    150.00 177.00   1.00    1.00    --  106.95 125.00-120.00   27
  9  ω    127.00 173.00   1.00    1.00    --  106.95 125.00 -60.00   46
 10  ω     95.00 150.00   1.00    1.00    --  106.95 125.00 -30.00   55
 11  ω     98.00 125.00   1.00    1.00    --  106.95 125.00-120.00   27
 12  ω     95.00 173.00   1.00    1.00    --  106.95 125.00   0.00   78
 13  ω    106.00 132.00   1.00    1.00    --  106.95 125.00 150.00   26
 14  ω     83.00 164.00   1.00    1.00    --  106.95  61.00  60.00   81
 15  ω     55.00 109.00   1.00    1.00    --  106.95 -95.00  30.00   54
 16  ω     43.00 129.00   1.00    1.00    --  106.95 -45.00  30.00   86
 17  ω     35.00 103.00   1.00    1.00    --  106.95 -95.00 -60.00   68
 18  ω   -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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.1771P)²+0.4655P] where P=(Fo²+2Fc²)/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 > 2σ(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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 0.20904(15) 0.39791(8) 0.92589(7) 0.0785(4) Uani 1 1 d . . . . .
Cl02 Cl 0.36729(16) 0.16950(9) 0.09891(7) 0.0865(4) Uani 1 1 d . . . . .
O003 O 0.3106(3) 0.37411(16) 0.72791(16) 0.0622(6) Uani 1 1 d . . . . .
O004 O 0.3962(3) 0.19110(17) 0.28716(17) 0.0616(6) Uani 1 1 d . . . . .
O005 O 0.3300(4) 0.0900(2) 0.62263(19) 0.0712(7) Uani 1 1 d . . . . .
O006 O 0.3169(4) 0.4728(2) 0.40267(19) 0.0774(7) Uani 1 1 d . . . . .
O007 O 0.1284(4) 0.6493(2) 0.3473(2) 0.0803(8) Uani 1 1 d . . . . .
O008 O 0.1998(4) -0.0928(2) 0.7075(2) 0.0760(7) Uani 1 1 d . . . . .
O009 O 0.2881(4) 0.5931(2) 0.04786(19) 0.0817(8) Uani 1 1 d . . . . .
N00A N 0.4246(4) 0.4070(2) 0.2705(2) 0.0589(6) Uani 1 1 d . . . . .
N00B N 0.3830(4) 0.1560(2) 0.7407(2) 0.0605(7) Uani 1 1 d . . . . .
O00C O 0.2329(5) -0.0281(2) 0.9885(2) 0.0947(10) Uani 1 1 d . . . . .
C00D C 0.2119(4) 0.4667(2) 0.7196(2) 0.0538(7) Uani 1 1 d . . . . .
C00E C 0.2662(4) 0.5651(2) 0.2300(2) 0.0549(7) Uani 1 1 d . . . . .
C00F C 0.3370(4) 0.4792(3) 0.3098(3) 0.0584(7) Uani 1 1 d . . . . .
C00G C 0.3250(4) 0.0843(2) 0.7127(2) 0.0550(7) Uani 1 1 d . . . . .
C00H C 0.3684(5) 0.3478(2) 0.6345(2) 0.0625(8) Uani 1 1 d . . . . .
C00I C 0.1654(5) 0.6464(3) 0.2508(3) 0.0611(8) Uani 1 1 d . . . . .
C00J C 0.1546(4) 0.4885(2) 0.8129(3) 0.0574(7) Uani 1 1 d . . . . .
C00K C 0.3146(4) 0.1021(2) 0.3079(3) 0.0547(7) Uani 1 1 d . . . . .
C00L C 0.2546(4) -0.0013(2) 0.8064(2) 0.0571(7) Uani 1 1 d . . . . .
C00M C 0.3193(5) 0.5416(3) 0.1339(2) 0.0597(8) Uani 1 1 d . . . . .
C00N C 0.1683(5) 0.5370(3) 0.6286(3) 0.0632(8) Uani 1 1 d . . . . .
C00O C 0.4225(5) 0.4354(3) 0.1589(2) 0.0631(8) Uani 1 1 d . . . . .
C00P C 0.4783(5) 0.2449(3) 0.6649(3) 0.0671(9) Uani 1 1 d . . . . .
C00Q C 0.2756(5) 0.0227(3) 0.8953(3) 0.0659(9) Uani 1 1 d . . . . .
C00R C 0.2932(4) 0.0818(3) 0.2222(3) 0.0618(8) Uani 1 1 d . . . . .
C00S C 0.0558(5) 0.5810(3) 0.8132(3) 0.0730(10) Uani 1 1 d . . . . .
C00T C 0.4199(5) 0.2154(3) 0.3746(2) 0.0605(8) Uani 1 1 d . . . . .
C00U C 0.3651(5) 0.1256(3) 0.8527(3) 0.0680(9) Uani 1 1 d . . . . .
C00V C 0.0673(5) 0.6303(3) 0.6296(3) 0.0724(10) Uani 1 1 d . . . . .
C00W C 0.1966(5) -0.0869(3) 0.7996(3) 0.0637(8) Uani 1 1 d . . . . .
C00X C 0.2555(5) 0.0329(3) 0.4069(3) 0.0652(8) Uani 1 1 d . . . . .
C00Y C 0.5209(5) 0.3142(3) 0.3282(3) 0.0662(8) Uani 1 1 d . . . . .
C00Z C 0.2110(5) -0.0076(3) 0.2338(4) 0.0747(10) Uani 1 1 d . . . . .
C010 C 0.1706(5) -0.0566(3) 0.4201(4) 0.0769(10) Uani 1 1 d . . . . .
C011 C 0.0138(5) 0.6512(3) 0.7214(4) 0.0782(11) Uani 1 1 d . . . . .
C012 C 0.1507(5) -0.0753(3) 0.3322(4) 0.0774(11) Uani 1 1 d . . . . .
C013 C 0.0885(6) 0.7372(3) 0.1742(3) 0.0792(11) Uani 1 1 d . . . . .
C014 C 0.1266(7) -0.1786(3) 0.8909(4) 0.0905(13) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00D O003 C00H 116.9(2) . . ?
C00K O004 C00T 117.6(2) . . ?
C00F N00A C00O 112.3(3) . . ?
C00F N00A C00Y 124.2(3) . . ?
C00Y N00A C00O 123.4(3) . . ?
C00G N00B C00P 122.2(3) . . ?
C00G N00B C00U 113.0(3) . . ?
C00U N00B C00P 124.1(3) . . ?
O003 C00D C00J 115.2(3) . . ?
O003 C00D C00N 124.7(3) . . ?
C00N C00D C00J 120.0(3) . . ?
C00F C00E C00M 107.4(3) . . ?
C00I C00E C00F 122.0(3) . . ?
C00I C00E C00M 130.6(3) . . ?
O006 C00F N00A 124.8(3) . . ?
O006 C00F C00E 125.0(3) . . ?
N00A C00F C00E 110.2(3) . . ?
O005 C00G N00B 125.7(3) . . ?
O005 C00G C00L 125.5(3) . . ?
N00B C00G C00L 108.9(3) . . ?
O003 C00H C00P 105.7(3) . . ?
O007 C00I C00E 120.0(3) . . ?
O007 C00I C013 114.5(3) . . ?
C00E C00I C013 125.5(3) . . ?
C00D C00J Cl01 118.8(2) . . ?
C00S C00J Cl01 121.0(3) . . ?
C00S C00J C00D 120.1(3) . . ?
O004 C00K C00R 115.9(3) . . ?
O004 C00K C00X 124.4(3) . . ?
C00R C00K C00X 119.6(3) . . ?
C00Q C00L C00G 107.5(3) . . ?
C00W C00L C00G 120.7(3) . . ?
C00W C00L C00Q 131.7(3) . . ?
O009 C00M C00E 129.0(3) . . ?
O009 C00M C00O 123.9(3) . . ?
C00E C00M C00O 107.1(3) . . ?
C00D C00N C00V 119.5(3) . . ?
N00A C00O C00M 103.0(3) . . ?
N00B C00P C00H 113.4(3) . . ?
O00C C00Q C00L 128.8(4) . . ?
O00C C00Q C00U 124.2(3) . . ?
C00L C00Q C00U 107.0(3) . . ?
C00K C00R Cl02 119.1(3) . . ?
C00K C00R C00Z 121.1(3) . . ?
C00Z C00R Cl02 119.8(3) . . ?
C011 C00S C00J 119.4(4) . . ?
O004 C00T C00Y 105.7(3) . . ?
N00B C00U C00Q 103.6(3) . . ?
C011 C00V C00N 119.8(4) . . ?
O008 C00W C00L 120.2(3) . . ?
O008 C00W C014 115.6(3) . . ?
C00L C00W C014 124.2(3) . . ?
C00K C00X C010 120.0(4) . . ?
N00A C00Y C00T 112.7(3) . . ?
C012 C00Z C00R 119.0(4) . . ?
C012 C010 C00X 119.2(4) . . ?
C00V C011 C00S 121.1(3) . . ?
C00Z C012 C010 121.1(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C00J 1.726(4) . ?
Cl02 C00R 1.731(4) . ?
O003 C00D 1.367(4) . ?
O003 C00H 1.442(4) . ?
O004 C00K 1.361(4) . ?
O004 C00T 1.444(4) . ?
O005 C00G 1.233(4) . ?
O006 C00F 1.252(4) . ?
O007 C00I 1.334(4) . ?
O008 C00W 1.322(4) . ?
O009 C00M 1.222(4) . ?
N00A C00F 1.330(4) . ?
N00A C00O 1.479(4) . ?
N00A C00Y 1.454(4) . ?
N00B C00G 1.348(4) . ?
N00B C00P 1.459(4) . ?
N00B C00U 1.453(4) . ?
O00C C00Q 1.230(4) . ?
C00D C00J 1.408(4) . ?
C00D C00N 1.378(5) . ?
C00E C00F 1.448(5) . ?
C00E C00I 1.350(5) . ?
C00E C00M 1.454(4) . ?
C00G C00L 1.461(4) . ?
C00H C00P 1.514(5) . ?
C00I C013 1.479(5) . ?
C00J C00S 1.384(5) . ?
C00K C00R 1.384(5) . ?
C00K C00X 1.384(5) . ?
C00L C00Q 1.452(5) . ?
C00L C00W 1.354(5) . ?
C00M C00O 1.518(5) . ?
C00N C00V 1.403(5) . ?
C00Q C00U 1.518(5) . ?
C00R C00Z 1.403(5) . ?
C00S C011 1.381(6) . ?
C00T C00Y 1.519(5) . ?
C00V C011 1.379(6) . ?
C00W C014 1.488(5) . ?
C00X C010 1.410(5) . ?
C00Z C012 1.372(6) . ?
C010 C012 1.397(6) . ?
