Synthesis, insecticidal activity, and structure-activity relationship (SAR) of anthranilic diamides analogs containing oxadiazole rings.
Li, Yuhao; Zhu, Hongjun; Chen, Kai; Liu, Rui; Khallaf, Abdalla; Zhang, Xiangning; Ni, Jueping; Organic & biomolecular chemistry 11 (2013) 3979–3988; doi:10.1039/c3ob40345a

data_7152948
_publ_section_title
;
 Synthesis, insecticidal activity, and structure-activity relationship
 (SAR) of anthranilic diamides analogs containing oxadiazole rings.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3979
_journal_page_last               3988
_journal_paper_doi               10.1039/c3ob40345a
_journal_volume                  11
_journal_year                    2013
_chemical_formula_sum            'C24 H14 Br2 Cl2 N6 O2'
_chemical_formula_weight         649.13
_chemical_name_systematic
;
3-bromo-N-(2-(3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl)-4
-chloro-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole
-5-carboxamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.53(3)
_cell_angle_beta                 80.97(3)
_cell_angle_gamma                86.17(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2290(18)
_cell_length_b                   11.142(2)
_cell_length_c                   12.526(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     1236.5(5)
_computing_cell_refinement       'CAD4 Software'
_computing_data_collection       'CAD4 Software(Enraf-Nonius,1985)'
_computing_data_reduction        'XCAD4(Harms & Wocadlo,1995)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'
_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  'Nonius cad4'
_diffrn_measurement_method       \w/2\q
_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  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4844
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.69
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.530
_exptl_absorpt_correction_T_max  0.7191
_exptl_absorpt_correction_T_min  0.5387
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(M. Takahashi, et al., 1989)'
_exptl_crystal_colour            colourlrss
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.118
_refine_diff_density_min         -0.875
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0657
_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^)+(0.0900P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1713
_reflns_number_gt                2523
_reflns_number_total             4538
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob40345a.txt
_cod_data_source_block           19
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1236.5(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7152948