Design, synthesis, crystal structure analysis, and insecticidal evaluation of phenylazoneonicotinoids.
Ye, Zhenjun; Xia, Shuang; Shao, Xusheng; Cheng, Jiagao; Xu, Xiaoyong; Xu, Zhiping; Li, Zhong; Qian, Xuhong; Journal of agricultural and food chemistry 59 (2011) 10615–10623; doi:10.1021/jf2029708

data_1501658
_publ_section_title
;
 Design, synthesis, crystal structure analysis, and insecticidal
 evaluation of phenylazoneonicotinoids.
;
_journal_issue                   19
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              10615
_journal_page_last               10623
_journal_paper_doi               10.1021/jf2029708
_journal_volume                  59
_journal_year                    2011
_chemical_formula_sum            'C16 H13 Cl3 N6 O2'
_chemical_formula_weight         427.67
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.256(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.4438(17)
_cell_length_b                   10.2569(11)
_cell_length_c                   11.1264(12)
_cell_measurement_reflns_used    3227
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.032
_cell_measurement_theta_min      4.723
_cell_volume                     1818.8(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0935
_diffrn_reflns_av_sigmaI/netI    0.0677
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9712
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61673
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.317
_exptl_crystal_size_min          0.223
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3565
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0824P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1448
_reflns_number_gt                2641
_reflns_number_total             3565
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jf2029708_si_001.cif
_cod_data_source_block           cd29554
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1501658