Copper(ii) complexes with terpene derivatives of ethylenediamine: synthesis, and antibacterial, antifungal and antioxidant activity
Gur'eva, Yana A.; Zalevskaya, Olga A.; Shevchenko, Oksana G.; Slepukhin, Pavel A.; Makarov, Vadim A.; Kuchin, Aleksandr V.; RSC Advances 12 (2022) 8841–8851; doi:10.1039/D2RA00223J

data_7244663
_publ_section_title
;
 Copper(ii) complexes with terpene derivatives of ethylenediamine:
 synthesis, and antibacterial, antifungal and antioxidant activity
;
_journal_issue                   15
_journal_name_full               'RSC Advances'
_journal_page_first              8841
_journal_page_last               8851
_journal_paper_doi               10.1039/D2RA00223J
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C14 H28 Cl2 Cu N2 O'
_chemical_formula_sum            'C14 H28 Cl2 Cu N2 O'
_chemical_formula_weight         374.82
_chemical_melting_point          397
_chemical_name_systematic
'Dichloro{N1,N1-dimethyl-N2-[(1R,2S,3R,4S)-2-oxy-1,7,7- trimethylbicyclo[2.2.1]heptane -3-yl]ethane-1,2-diamine-N1,N2,O}copper(II)'
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-08-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-09-30 deposited with the CCDC.	2022-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.652(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1957(10)
_cell_length_b                   12.0448(13)
_cell_length_c                   10.685(2)
_cell_measurement_reflns_used    1504
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.3600
_cell_measurement_theta_min      3.8210
_cell_volume                     907.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     22.00  47.00   1.00   50.00    --   22.36  37.00-124.00   25
  2  \w    -50.00 -24.00   1.00   50.00    --   22.36 -37.00  79.00   26
  3  \w    -25.00  49.00   1.00   50.00    --  -23.92  37.00-124.00   74
  4  \w    -94.00   2.00   1.00   50.00    --  -23.92 -37.00  79.00   96
  5  \w     35.00  90.00   1.00   50.00    --   22.36 178.00  30.00   55
  6  \w     36.00  96.00   1.00   50.00    --   22.36 178.00  90.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0507701000
_diffrn_orient_matrix_UB_12      -0.0251358000
_diffrn_orient_matrix_UB_13      0.0566657000
_diffrn_orient_matrix_UB_21      -0.0770034000
_diffrn_orient_matrix_UB_22      0.0106579000
_diffrn_orient_matrix_UB_23      0.0306047000
_diffrn_orient_matrix_UB_31      -0.0402349000
_diffrn_orient_matrix_UB_32      -0.0521846000
_diffrn_orient_matrix_UB_33      -0.0210985000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_unetI/netI     0.1087
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6643
_diffrn_reflns_point_group_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.738
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.886
_diffrn_reflns_theta_min         3.569
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.496
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'bluish green'
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       plate
_exptl_crystal_F_000             394
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.767
_refine_diff_density_min         -0.913
_refine_diff_density_rms         0.145
_refine_ls_abs_structure_details
;
 Flack x determined using 682 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_coef       0.086(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4237
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1501
_refine_ls_R_factor_gt           0.0985
_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^)+(0.1546P)^2^+1.3058P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2429
_refine_ls_wR_factor_ref         0.3056
_reflns_Friedel_coverage         0.648
_reflns_Friedel_fraction_full    0.765
_reflns_Friedel_fraction_max     0.607
_reflns_number_gt                2506
_reflns_number_total             4237
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra00223j2.cif
_cod_data_source_block           exp_834
_cod_database_code               7244663
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.593
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1A
 0.85 with sigma of 0.01
 Cu1-H1A
 2.749365 with sigma of 0.02
 C1-H1A
 1.894545 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 N1(H1), C1(H1B), C2(H2), C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C10(H10A,H10B), C11(H11A,H11B)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              67331
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.579
_oxdiff_exptl_absorpt_empirical_full_min 0.635