Semisynthesis of esters and oxime esters/sulfonates from furyl-ring-based acetylation derivatives of fraxinellone as insecticidal agents
Guo, Yong; Yang, Ruige; Xu, Hui; RSC Adv. 7 (2017) 28009–; doi:10.1039/C7RA03588H

data_7228341
_publ_section_title
;
 Semisynthesis of esters and oxime esters/sulfonates from furyl-ring-based
 acetylation derivatives of fraxinellone as insecticidal agents
;
_journal_issue                   45
_journal_name_full               'RSC Adv.'
_journal_page_first              28009
_journal_paper_doi               10.1039/C7RA03588H
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C24 H25 N O5'
_chemical_formula_sum            'C24 H25 N O5'
_chemical_formula_weight         407.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-12-15
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_audit_update_record
;
2016-12-29 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.192(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2307(5)
_cell_length_b                   23.9115(14)
_cell_length_c                   11.3903(10)
_cell_measurement_reflns_used    2009
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.2240
_cell_measurement_theta_min      3.6330
_cell_volume                     2141.5(3)
_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
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.6066
_diffrn_measurement_details
;
  1 omega  -20.00   22.00   1.2000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -99.0000   90.0000 35

  2 omega -101.00  -71.00   1.2000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  178.0000 -150.0000 25

  3 omega  -15.00   63.00   1.2000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -99.0000 -150.0000 65

  4 omega  -43.00   41.00   1.2000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075    0.0000   90.0000 70
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0254648000
_diffrn_orient_matrix_UB_12      -0.0214761000
_diffrn_orient_matrix_UB_13      -0.0446403000
_diffrn_orient_matrix_UB_21      -0.0164895000
_diffrn_orient_matrix_UB_22      -0.0179135000
_diffrn_orient_matrix_UB_23      0.0447709000
_diffrn_orient_matrix_UB_31      -0.0849909000
_diffrn_orient_matrix_UB_32      0.0098917000
_diffrn_orient_matrix_UB_33      -0.0157824000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8238
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.16
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44652
_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    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.176
_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   -0.8(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         5888
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1856
_reflns_number_gt                3806
_reflns_number_total             5888
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ra03588h2.cif
_cod_data_source_block           gy_468
_cod_original_cell_volume        2141.6(3)
_cod_database_code               7228341
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H27A,H27B} of C27, H31 of C31, {H29A,H29B} of C29, {H28A,H28B} of C28, H7
  of C7, {H5A,H5B} of C5, {H4A,H4B} of C4, {H3A,H3B} of C3, H46 of C46, H45 of
  C45, H43 of C43, H42 of C42, H38 of C38, H36 of C36, H22 of C22, H21 of C21,
  H19 of C19, H18 of C18, H14 of C14, H12 of C12
 At 1.5 times of:
  {H33A,H33B,H33C} of C33, {H9A,H9B,H9C} of C9, {H48A,H48B,H48C} of C48,
  {H47A,H47B,H47C} of C47, {H34A,H34B,H34C} of C34, {H24A,H24B,H24C} of C24,
  {H23A,H23B,H23C} of C23, {H10A,H10B,H10C} of C10
2.a Ternary CH refined with riding coordinates:
 C31(H31), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C3(H3A,H3B), C4(H4A,H4B),
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C36(H36), C38(H38), C42(H42), C43(H43), C45(H45), C46(H46), C12(H12),
 C14(H14), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C47(H47A,H47B,H47C), C48(H48A,H48B,
 H48C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C23(H23A,H23B,H23C), C24(H24A,
 H24B,H24C)
;