Structure and catalytic properties of novel copper isatin Schiff base complexes
Smirnov, Andrey S.; Martins, Luísa M. D. R. S.; Nikolaev, Dmitriy N.; Manzhos, Roman A.; Gurzhiy, Vlad V.; Krivenko, Alexander G.; Nikolaenko, Kirill O.; Belyakov, Alexander V.; Garabadzhiu, Alexander V.; Davidovich, Pavel B.; New Journal of Chemistry 43 (2019) 188–; doi:10.1039/C8NJ02718H

data_7057913
_publ_section_title
;
 Structure and catalytic properties of novel copper isatin Schiff base
 complexes
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              188
_journal_paper_doi               10.1039/C8NJ02718H
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety
'C21 H24 Br Cu N2 O, C21 H24 Br0.7 Cu0.7 N2 O'
_chemical_formula_sum            'C42 H48 Br1.7 Cu1.7 N4 O2'
_chemical_formula_weight         884.71
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-15
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                99.747(3)
_cell_angle_beta                 108.723(3)
_cell_angle_gamma                102.672(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0842(4)
_cell_length_b                   11.7852(5)
_cell_length_c                   17.1333(5)
_cell_measurement_reflns_used    10674
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.4800
_cell_measurement_theta_min      3.9740
_cell_volume                     1997.24(14)
_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      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -24.00   36.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537   38.0000   60.0000 60

  2 omega  -60.00   32.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537   57.0000  150.0000 92

  3 omega    3.00   76.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       40.2537  -99.0000 -150.0000 73

  4 omega   68.00  111.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -60.0000 43

  5 omega   77.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 38

  6 omega   80.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 35

  7 omega   90.00  147.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  120.0000 57

  8 omega  108.00  133.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000    0.0000 25

  9 omega  120.00  171.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   60.0000 51

 10 omega  123.00  175.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 52

 11 omega  102.00  155.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   60.0000 53

 12 omega  112.00  156.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 44

 13 omega  126.00  154.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 28

 14 omega  152.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 25

 15 omega   99.00  139.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 40

 16 omega   82.00  170.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000    0.0000 88

 17 omega  113.00  138.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 25

 18 omega   92.00  147.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 55

 19 omega   79.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 36

 20 omega   68.00  111.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 43

 21 omega   72.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -180.0000 25

 22 omega   60.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 25

 23 omega   51.00   78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 27

 24 omega   45.00   74.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 29

 25 omega   67.00   94.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -180.0000 27

 26 omega   74.00  107.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 33

 27 omega   41.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 56

 28 omega   40.00   66.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 26

 29 omega   29.00  101.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -180.0000 72

 30 omega   39.00  100.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -54.0000  -30.9678 61

 31 omega   82.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -87.0000   25.4318 44

 32 omega   82.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 33

 33 omega   81.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 28

 34 omega   72.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 43

 35 omega   64.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 25

 36 omega   52.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 33

 37 omega   52.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   30.0000 44

 38 omega   49.00   76.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 27

 39 omega   55.00   80.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 25

 40 omega   40.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -56.0000   64.0000 58

 41 omega   44.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 25

 42 omega   38.00   65.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   30.0000 27

 43 omega   30.00   82.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 52

 44 omega   84.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   60.0000 29

 45 omega   93.00  122.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 29

 46 omega  102.00  132.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  150.0000 30

 47 omega   63.00  100.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -60.0000 37

 48 omega   68.00   93.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -150.0000 25

 49 omega  120.00  147.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -150.0000 27

 50 omega -109.00  -49.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -57.0000    0.0000 60

 51 omega -114.00  -16.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -57.0000  -90.0000 98

 52 omega -127.00  -72.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  178.0000  -60.0000 55

 53 omega   85.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   56.0000 -153.0000 36

 54 omega -112.00  -11.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -56.0000   64.0000 101

 55 omega -114.00  -14.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -38.0000  120.0000 100

 56 omega    6.00   31.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   89.0000  -66.8482 25

 57 omega   13.00   38.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   81.0000  175.9105 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0846063000
_diffrn_orient_matrix_UB_12      0.0723537000
_diffrn_orient_matrix_UB_13      -0.0478833000
_diffrn_orient_matrix_UB_21      0.1166165000
_diffrn_orient_matrix_UB_22      0.1162286000
_diffrn_orient_matrix_UB_23      0.0462998000
_diffrn_orient_matrix_UB_31      0.0529738000
_diffrn_orient_matrix_UB_32      -0.0224226000
_diffrn_orient_matrix_UB_33      -0.0723017000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27863
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.486
_diffrn_reflns_theta_min         3.981
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.451
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70706
_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            red
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       prism
_exptl_crystal_F_000             906
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.246
_refine_diff_density_min         -0.885
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0708P)^2^+2.2897P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6860
_reflns_number_total             7935
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj02718h2.cif
_cod_data_source_block           pd_127
_cod_depositor_comments
'Adding full bibliography for 7057891--7057914.cif.'
_cod_original_cell_volume        1997.24(13)
_cod_original_formula_sum        'C42 H48 Br1.70 Cu1.70 N4 O2'
_cod_database_code               7057913
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 94.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.07
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C24B) = Uanis(C24A)
Uanis(C23B) = Uanis(C23A)
Uanis(C22A) = Uanis(C22B)
3. Others
 Sof(C22B)=Sof(H22B)=Sof(C23B)=Sof(H23D)=Sof(H23E)=Sof(H23F)=Sof(C24B)=
 Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C24A)=
 Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(Br25A)=Sof(Cu25A)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C19(H19), C22(H22), C19A(H19A), C22A(H22A), C22B(H22B)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C15(H15), C16(H16), C17(H17), C6A(H6A),
 C7A(H7A), C8A(H8A), C9A(H9A), C15A(H15A), C16A(H16A), C17A(H17A)
4.c Idealised Me refined as rotating group:
 C10(H10D,H10E,H10F), C20(H20D,H20E,H20F), C21(H21D,H21E,H21F), C23(H23G,H23H,
 H23I), C24(H24G,H24H,H24I), C10A(H10A,H10B,H10C), C20A(H20A,H20B,H20C),
 C21A(H21A,H21B,H21C), C23A(H23A,H23B,H23C), C23B(H23D,H23E,H23F), C24A(H24A,
 H24B,H24C), C24B(H24D,H24E,H24F)
;