Design, synthesis, antibacterial and insecticidal activities of novel N-phenylpyrazole fraxinellone hybrid compounds
Guo, Yong; Wang, Xiaoguang; Qu, Lailiang; Xu, Shengnan; Zhao, Yi; Xie, Ruoqian; Huang, Mengxing; Zhang, Yanbing; RSC Adv. 7 (2017) 11796–; doi:10.1039/C6RA28064A

data_7227707
_publ_section_title
;
 Design, synthesis, antibacterial and insecticidal activities of novel
 N-phenylpyrazole fraxinellone hybrid compounds
;
_journal_issue                   19
_journal_name_full               'RSC Adv.'
_journal_page_first              11796
_journal_paper_doi               10.1039/C6RA28064A
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H16 F2 N2 O3'
_chemical_formula_sum            'C21 H16 F2 N2 O3'
_chemical_formula_weight         382.36
_chemical_name_systematic        YG-90
_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     iterative
_audit_creation_date             2016-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-06 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.323(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9128(5)
_cell_length_b                   13.2459(9)
_cell_length_c                   8.7406(6)
_cell_measurement_reflns_used    782
_cell_measurement_temperature    289.97(10)
_cell_measurement_theta_max      21.4530
_cell_measurement_theta_min      3.8690
_cell_volume                     904.02(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      289.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -11.00   17.50   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000   90.0000 19

  2 omega   -8.00   19.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -90.0000 18

  3 omega  -52.00   29.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000 -120.0000 54

  4 omega    1.00   86.50   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000   60.0000 57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0401025000
_diffrn_orient_matrix_UB_12      0.0387486000
_diffrn_orient_matrix_UB_13      0.0371302000
_diffrn_orient_matrix_UB_21      0.0262343000
_diffrn_orient_matrix_UB_22      0.0361150000
_diffrn_orient_matrix_UB_23      -0.0513235000
_diffrn_orient_matrix_UB_31      -0.0771717000
_diffrn_orient_matrix_UB_32      -0.0078784000
_diffrn_orient_matrix_UB_33      -0.0524348000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3576
_diffrn_reflns_point_group_measured_fraction_full 0.671
_diffrn_reflns_point_group_measured_fraction_max 0.671
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         3.572
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_coef       0.027(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         2393
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1765
_reflns_Friedel_coverage         0.288
_reflns_Friedel_fraction_full    0.315
_reflns_Friedel_fraction_max     0.314
_reflns_number_gt                1611
_reflns_number_total             2393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra28064a2.cif
_cod_data_source_block           yg90
_cod_database_code               7227707
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3-C19
 1.36 with sigma of 0.01
3. Rigid bond restraints
 C19, O3
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
4.a Ternary CH refined with riding coordinates:
 C16(H16)
4.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C7(H7), C18(H18), C19(H19), C20(H20)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-05-13
_olex2_submission_special_instructions 'No special instructions were received'