N'-Nitro-2-hydrocarbylidenehydrazinecarboximidamides: Design, Synthesis, Crystal Structure, Insecticidal Activity, and Structure-Activity Relationships.
Su, Wangcang; Zhou, Yihui; Ma, Yongqiang; Wang, Lei; Zhang, Zheng; Rui, Changhui; Duan, Hongxia; Qin, Zhaohai; Journal of agricultural and food chemistry 60 (2012) 5028–5034; doi:10.1021/jf300616x

data_1507654
_publ_section_title
;
 N'-Nitro-2-hydrocarbylidenehydrazinecarboximidamides: Design, Synthesis,
 Crystal Structure, Insecticidal Activity, and Structure-Activity
 Relationships.
;
_journal_issue                   20
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              5028
_journal_page_last               5034
_journal_paper_doi               10.1021/jf300616x
_journal_volume                  60
_journal_year                    2012
_chemical_formula_moiety         'C11 H15 Cl N6 O2'
_chemical_formula_sum            'C11 H15 Cl N6 O2'
_chemical_formula_weight         298.74
_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                 114.164(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.738(2)
_cell_length_b                   17.846(4)
_cell_length_c                   9.701(3)
_cell_measurement_reflns_used    3525
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.14
_cell_volume                     1380.2(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6457
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.8908
_exptl_absorpt_correction_T_min  0.8714
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0521
_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^)+(0.0425P)^2^+0.7054P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                2823
_reflns_number_total             3108
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jf300616x_si_003.cif
_cod_data_source_block           sa987
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1507654