Synthesis and quantitative structure-activity relationship (QSAR) study of C7-oxime ester derivatives of obacunone as insecticidal agents
Yu, Xiang; Shi, Danfeng; Zhi, Xiaoyan; Li, Qin; Yao, Xiaojun; xu, hui; RSC Adv.  (2015) –; doi:10.1039/C5RA01411E

data_7220031
_publ_section_title
;
 Synthesis and quantitative structure-activity relationship (QSAR) study
 of C7-oxime ester derivatives of obacunone as insecticidal agents
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA01411E
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C34 H37 N O8'
_chemical_formula_sum            'C34 H37 N O8'
_chemical_formula_weight         587.65
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-12-14
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7476(9)
_cell_length_b                   14.2825(12)
_cell_length_c                   19.7165(17)
_cell_measurement_reflns_used    1673
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.0190
_cell_measurement_theta_min      3.4230
_cell_volume                     3026.5(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9963
_diffrn_measured_fraction_theta_max 0.8221
_diffrn_measurement_details
;
  1 omega  -38.00  -11.00   1.5000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262   57.0000  -30.0000 18

  2 omega   27.00   54.00   1.5000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262   38.0000 -180.0000 18

  3 omega  -18.00   12.00   1.5000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -99.0000  120.0000 20

  4 omega  -50.00   11.50   1.5000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262   38.0000 -180.0000 41

  5 omega   24.00   96.00   1.5000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   77.0000   30.0000 48

  6 omega  -20.00   17.50   1.5000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -99.0000  -90.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0638008000
_diffrn_orient_matrix_UB_12      0.0025093000
_diffrn_orient_matrix_UB_13      0.0091255000
_diffrn_orient_matrix_UB_21      -0.0155859000
_diffrn_orient_matrix_UB_22      -0.0287682000
_diffrn_orient_matrix_UB_23      -0.0281227000
_diffrn_orient_matrix_UB_31      0.0070854000
_diffrn_orient_matrix_UB_32      -0.0404918000
_diffrn_orient_matrix_UB_33      0.0205297000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12084
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.03
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.5(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         5521
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1435
_reflns_number_gt                3176
_reflns_number_total             5521
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra01411e2.cif
_cod_data_source_block           yx_324
_cod_database_code               7220031
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H29 of C29, H32 of C32, H31 of C31, H33 of C33, {H13A,H13B} of C13, H15 of
  C15, H3 of C3, H4 of C4, H2 of C2, H1A of C1A, {H11A,H11B} of C11, H10 of C10,
   {H9A,H9B} of C9, H20 of C20, H19B of C19B, H19 of C19, H20B of C20B, H21B of
  C21B, H21 of C21
 At 1.5 times of:
  {H34A,H34B,H34C} of C34, {H25A,H25B,H25C} of C25, {H24A,H24B,H24C} of C24,
  {H23A,H23B,H23C} of C23, {H22A,H22B,H22C} of C22
2. Restrained distances
 C20B-C19B
 1.4 with sigma of 0.02
 H26A-C26
 0.94 with sigma of 0.01
 H26B-C26
 0.94 with sigma of 0.01
 H26C-C26
 0.94 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C21) ~ Ueq, Uanis(C19B) ~ Ueq, Uanis(O4) ~ Ueq, Uanis(C20B) ~ Ueq, Uanis(C20) ~ Ueq, Uanis(O20B) ~ Ueq, Uanis(C19) ~ Ueq, Uanis(C21B) ~ Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: O4(0.6) O20B(0.4) C19(0.6) H19(0.6) C19B(0.4) H19B(0.4) C20(0.6)
 H20(0.6) C20B(0.4) H20B(0.4) C21(0.6) H21(0.6) C21B(0.4) H21B(0.4)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C10(H10), C15(H15)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B)
5.c Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C3(H3), C19(H19), C19B(H19B), C20(H20), C20B(H20B), C21(H21),
 C21B(H21B), C29(H29), C31(H31), C32(H32), C33(H33)
5.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C34(H34A,H34B,H34C)
;