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_7227706
_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 ad
_chemical_formula_moiety         'C21 H17 Br N2 O3'
_chemical_formula_sum            'C21 H17 Br N2 O3'
_chemical_formula_weight         425.27
_chemical_name_systematic        YG-98
_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
_audit_creation_date             2016-06-03
_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                 111.940(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5895(10)
_cell_length_b                   12.3063(10)
_cell_length_c                   9.7721(9)
_cell_measurement_reflns_used    503
_cell_measurement_temperature    295.05(10)
_cell_measurement_theta_max      19.2390
_cell_measurement_theta_min      4.1740
_cell_volume                     958.15(18)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_details
;
  1 omega   35.00   95.00   2.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       21.0541  178.0000  -90.0000 30

  2 omega   44.00   90.00   2.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       21.0541   77.0000 -150.0000 23

  3 omega  -20.00   24.00   2.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.8354  -99.0000 -120.0000 22

  4 omega   34.00   98.00   2.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       21.0541 -178.0000   90.0000 32
;
_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      -0.0724366000
_diffrn_orient_matrix_UB_12      0.0235609000
_diffrn_orient_matrix_UB_13      0.0061145000
_diffrn_orient_matrix_UB_21      -0.0514152000
_diffrn_orient_matrix_UB_22      -0.0288698000
_diffrn_orient_matrix_UB_23      -0.0636935000
_diffrn_orient_matrix_UB_31      -0.0052361000
_diffrn_orient_matrix_UB_32      -0.0439974000
_diffrn_orient_matrix_UB_33      0.0450186000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.1273
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4032
_diffrn_reflns_point_group_measured_fraction_full 0.775
_diffrn_reflns_point_group_measured_fraction_max 0.658
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.860
_diffrn_reflns_theta_min         3.986
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78101
_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    1.474
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 367 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3317
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1506
_refine_ls_R_factor_gt           0.0688
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0538P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1798
_reflns_Friedel_coverage         0.429
_reflns_Friedel_fraction_full    0.530
_reflns_Friedel_fraction_max     0.414
_reflns_number_gt                1665
_reflns_number_total             3317
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra28064a2.cif
_cod_data_source_block           yg_98
_cod_original_cell_volume        958.16(18)
_cod_database_code               7227706
_reflns_odcompleteness_completeness 99.56
_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.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C18(H18), C19(H19), C20(H20)
2.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 2016-05-16
_olex2_submission_special_instructions 'No special instructions were received'