data_IM4
# 
_chem_comp.id                                    IM4 
_chem_comp.name                                  (2E)-1-[(6-chloropyridin-3-yl)methyl]-N-nitroimidazolidin-2-imine 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C9 H10 Cl N5 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         imidacloprid 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-02-11 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        255.661 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     IM4 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        3C79 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
IM4 C5  C5  C  0  1 Y N N 55.275 -20.512 -6.923 1.944  1.581  0.530  C5  IM4 1  
IM4 C6  C6  C  0  1 Y N N 54.261 -20.401 -7.930 3.136  1.089  0.024  C6  IM4 2  
IM4 C1  C1  C  0  1 Y N N 53.029 -19.851 -7.656 3.321  -0.280 -0.056 C1  IM4 3  
IM4 CL7 CL7 CL 0  0 N N N 51.891 -19.734 -8.658 4.811  -0.909 -0.687 CL7 IM4 4  
IM4 N2  N2  N  0  1 Y N N 52.934 -19.368 -6.365 2.378  -1.112 0.341  N2  IM4 5  
IM4 C3  C3  C  0  1 Y N N 53.853 -19.478 -5.392 1.231  -0.679 0.827  C3  IM4 6  
IM4 C4  C4  C  0  1 Y N N 55.084 -20.091 -5.623 0.976  0.674  0.937  C4  IM4 7  
IM4 C8  C8  C  0  1 N N N 56.196 -20.182 -4.526 -0.336 1.160  1.499  C8  IM4 8  
IM4 N9  N9  N  0  1 N N N 55.638 -20.115 -3.167 -1.302 1.325  0.411  N9  IM4 9  
IM4 C13 C13 C  0  1 N N N 55.598 -18.947 -2.308 -1.503 2.553  -0.373 C13 IM4 10 
IM4 C12 C12 C  0  1 N N N 54.903 -19.435 -1.010 -2.619 2.179  -1.367 C12 IM4 11 
IM4 N11 N11 N  0  1 N N N 54.656 -20.839 -1.293 -2.930 0.780  -1.040 N11 IM4 12 
IM4 C10 C10 C  0  1 N N N 55.081 -21.137 -2.531 -2.140 0.377  -0.034 C10 IM4 13 
IM4 N14 N14 N  0  1 N N N 55.028 -22.355 -3.086 -2.188 -0.864 0.486  N14 IM4 14 
IM4 N15 N15 N  1  1 N N N 54.507 -23.277 -2.449 -3.086 -1.698 0.084  N15 IM4 15 
IM4 O16 O16 O  0  1 N N N 54.827 -24.599 -2.449 -4.193 -1.693 0.592  O16 IM4 16 
IM4 O17 O17 O  -1 1 N N N 53.998 -22.942 -1.144 -2.827 -2.490 -0.804 O17 IM4 17 
IM4 H5  H5  H  0  1 N N N 56.228 -20.943 -7.193 1.773  2.644  0.609  H5  IM4 18 
IM4 H6  H6  H  0  1 N N N 54.469 -20.758 -8.928 3.912  1.766  -0.303 H6  IM4 19 
IM4 H3  H3  H  0  1 N N N 53.634 -19.084 -4.411 0.482  -1.390 1.143  H3  IM4 20 
IM4 H8  H8  H  0  1 N N N 56.726 -21.139 -4.641 -0.716 0.433  2.216  H8  IM4 21 
IM4 H8A H8A H  0  1 N N N 56.875 -19.327 -4.658 -0.184 2.117  1.999  H8A IM4 22 
IM4 H13 H13 H  0  1 N N N 56.612 -18.575 -2.098 -1.824 3.370  0.273  H13 IM4 23 
IM4 H7  H7  H  0  1 N N N 55.061 -18.108 -2.775 -0.590 2.820  -0.905 H7  IM4 24 
IM4 H12 H12 H  0  1 N N N 55.545 -19.302 -0.127 -3.494 2.811  -1.215 H12 IM4 25 
IM4 H9  H9  H  0  1 N N N 53.989 -18.873 -0.768 -2.261 2.264  -2.393 H9  IM4 26 
IM4 H10 H10 H  0  1 N N N 54.232 -21.487 -0.660 -3.597 0.234  -1.484 H10 IM4 27 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
IM4 C5  C4  SING Y N 1  
IM4 C5  H5  SING N N 2  
IM4 C6  C5  DOUB Y N 3  
IM4 C6  C1  SING Y N 4  
IM4 C6  H6  SING N N 5  
IM4 C1  N2  DOUB Y N 6  
IM4 CL7 C1  SING N N 7  
IM4 N2  C3  SING Y N 8  
IM4 C3  H3  SING N N 9  
IM4 C4  C3  DOUB Y N 10 
IM4 C4  C8  SING N N 11 
IM4 C8  N9  SING N N 12 
IM4 C8  H8  SING N N 13 
IM4 C8  H8A SING N N 14 
IM4 N9  C10 SING N N 15 
IM4 N9  C13 SING N N 16 
IM4 C13 C12 SING N N 17 
IM4 N11 C12 SING N N 18 
IM4 C10 N11 SING N N 19 
IM4 N14 C10 DOUB N N 20 
IM4 N14 N15 SING N N 21 
IM4 N15 O17 SING N N 22 
IM4 O16 N15 DOUB N N 23 
IM4 C13 H13 SING N N 24 
IM4 C13 H7  SING N E 25 
IM4 C12 H12 SING N N 26 
IM4 C12 H9  SING N N 27 
IM4 N11 H10 SING N N 28 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
IM4 SMILES           ACDLabs              10.04 [O-][N+](=O)/N=C1\NCCN1Cc2cnc(Cl)cc2                                                                        
IM4 InChI            InChI                1.02b InChI=1/C9H10ClN5O2/c10-8-2-1-7(5-12-8)6-14-4-3-11-9(14)13-15(16)17/h1-2,5H,3-4,6H2,(H,11,13)/f/h11H/b13-9+ 
IM4 InChIKey         InChI                1.02b YWTYJOPNNQFBPC-DLSJENCCDA                                                                                   
IM4 SMILES_CANONICAL CACTVS               3.341 [O-][N+](=O)\N=C\1NCCN\1Cc2ccc(Cl)nc2                                                                       
IM4 SMILES           CACTVS               3.341 [O-][N+](=O)N=C1NCCN1Cc2ccc(Cl)nc2                                                                          
IM4 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ncc1CN\2CCN/C2=N\[N+](=O)[O-])Cl                                                                       
IM4 SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ncc1CN2CCNC2=N[N+](=O)[O-])Cl                                                                          
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
IM4 "SYSTEMATIC NAME" ACDLabs              10.04 (2E)-1-[(6-chloropyridin-3-yl)methyl]-N-nitroimidazolidin-2-imine        
IM4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (NE)-N-[1-[(6-chloropyridin-3-yl)methyl]imidazolidin-2-ylidene]nitramide 
# 
