(2<i>E</i>)-1-[(6-Chloropyridin-3-yl)methyl]-<i>N</i>-nitroimidazolidin-2-imine (imidachloprid)
Chopra, Deepak; Mohan, T. P.; Rao, K. S.; Guru Row, T. N.; Acta Crystallographica Section E 60 (2004) o2415–o2417; doi:10.1107/S1600536804029824

data_2204775
_publ_section_title
;(2<i>E</i>)-1-[(6-Chloropyridin-3-yl)methyl]-<i>N</i>-nitroimidazolidin-2-imine
 (imidachloprid)
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2415
_journal_page_last               o2417
_journal_paper_doi               10.1107/S1600536804029824
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C9 H10 Cl N5 O2'
_chemical_formula_moiety         'C9 H10 Cl N5 O2'
_chemical_formula_sum            'C9 H10 Cl N5 O2'
_chemical_formula_weight         255.67
_chemical_name_common            Imidachloprid
_chemical_name_systematic
;
(2E)-1-[(6-Chloropyridin-3-yl)methyl]-N-nitroimidazolidin-2-imine
(imidachloprid)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 99.220(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.290(8)
_cell_length_b                   4.839(2)
_cell_length_c                   11.784(5)
_cell_measurement_reflns_used    865
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      1.4
_cell_volume                     1085.8(8)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8430
_diffrn_reflns_reduction_process
;
 ?
;
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.79
_diffrn_reflns_theta_min         1.07
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  0.9526
_exptl_absorpt_correction_T_min  0.8416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.323
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0928P)^2^+0.1346P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1619
_reflns_number_gt                1822
_reflns_number_total             2364
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ob6440.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204775
_cod_database_fobs_code          2204775