Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: design, synthesis, crystal structure, and insecticidal activities.
Shao, Xusheng; Fu, Hua; Xu, Xiaoyong; Xu, Xinglei; Liu, Zewen; Li, Zhong; Qian, Xuhong; Journal of agricultural and food chemistry 58 (2010) 2696–2702; doi:10.1021/jf902531y

data_1502655
_publ_section_title
;
 Divalent and oxabridged neonicotinoids constructed by dialdehydes and
 nitromethylene analogues of imidacloprid: design, synthesis, crystal
 structure, and insecticidal activities.
;
_journal_issue                   5
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              2696
_journal_page_last               2702
_journal_paper_doi               10.1021/jf902531y
_journal_volume                  58
_journal_year                    2010
_chemical_formula_sum            'C14.5 H16 Cl2 N4 O3'
_chemical_formula_weight         365.21
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.678(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.130(4)
_cell_length_b                   9.2835(18)
_cell_length_c                   15.475(3)
_cell_measurement_reflns_used    1225
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.395
_cell_measurement_theta_min      5.398
_cell_volume                     3175.8(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0985
_diffrn_reflns_av_sigmaI/netI    0.1021
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7954
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7876
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.369
_exptl_crystal_size_min          0.327
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1271
_refine_ls_R_factor_gt           0.0744
_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^)+(0.0903P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1670
_refine_ls_wR_factor_ref         0.1990
_reflns_number_gt                1612
_reflns_number_total             2958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jf902531y_si_001.cif
_cod_data_source_block           cd28579
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3175.8(11)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C14.50 H16 Cl2 N4 O3'
_cod_database_code               1502655