Pyrrole- and dihydropyrrole-fused neonicotinoids: design, synthesis, and insecticidal evaluation.
Ye, Zhenjun; Shi, Lina; Shao, Xusheng; Xu, Xiaoyong; Xu, Zhiping; Li, Zhong; Journal of agricultural and food chemistry 61 (2013) 312–319; doi:10.1021/jf3044132

data_1508819
_publ_section_title
;
 Pyrrole- and dihydropyrrole-fused neonicotinoids: design, synthesis, and
 insecticidal evaluation.
;
_journal_issue                   2
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              312
_journal_page_last               319
_journal_paper_doi               10.1021/jf3044132
_journal_volume                  61
_journal_year                    2013
_chemical_formula_sum            'C15 H19 Cl N4 O4'
_chemical_formula_weight         354.79
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.6146(8)
_cell_length_b                   7.7855(5)
_cell_length_c                   35.607(2)
_cell_measurement_reflns_used    4625
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.538
_cell_measurement_theta_min      4.576
_cell_volume                     3219.8(4)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            18236
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.14
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8034
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.52(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         7031
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0613P)^2^+0.0371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                5144
_reflns_number_total             7031
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jf3044132_si_002.cif
_cod_data_source_block           cd201408
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_sg_symbol_H-M      Pca2(1)
_cod_database_code               1508819