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#$Date: 2022-10-18 01:58:21 +0300 (Tue, 18 Oct 2022) $
#$Revision: 278619 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/14/7711499.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7711499
loop_
_publ_author_name
'Maxim, Catalin'
'Ene, Cristian D.'
'Nicolau, Ioana'
'Ruta, Lavinia L.'
'Farcasanu, Ileana C.'
_publ_section_title
;
 Enantiomeric pairs of copper(ii) complexes with tridentate Schiff bases
 derived from R- and S-methionine: the role of decorating organic groups
 of the ligand in crystal packing and biological activity
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02620A
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C14 H17 Cu N O4 S'
_chemical_formula_sum            'C14 H17 Cu N O4 S'
_chemical_formula_weight         358.88
_chemical_name_common            1?[Cu(S-3-HOMe-5-Me-salmet)]
_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     dual
_audit_creation_date             2022-01-30
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-06-05 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.347(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.160(2)
_cell_length_b                   5.6142(6)
_cell_length_c                   12.674(2)
_cell_measurement_reflns_used    6042
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.02
_cell_measurement_theta_min      5.39
_cell_volume                     781.2(2)
_computing_cell_refinement       X-Area
_computing_data_collection       X-Area
_computing_data_reduction        X-Area
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'stoe ipds ii'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8755
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        24.757
_diffrn_reflns_theta_max         24.757
_diffrn_reflns_theta_min         3.456
_diffrn_source                   sealed
_exptl_absorpt_coefficient_mu    1.545
_exptl_absorpt_correction_T_max  0.9765
_exptl_absorpt_correction_T_min  0.8132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_description       block
_exptl_crystal_F_000             370
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 732 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0396
_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/[σ²(Fo²)+(0.0560P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.850
_reflns_Friedel_fraction_max     0.850
_reflns_number_gt                2028
_reflns_number_total             2489
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt02620a2.cif
_cod_data_source_block           2S
_cod_original_cell_volume        781.1(2)
_cod_database_code               7711499
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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
 H4-O4
 1.054 with sigma of 0.001
3.a Ternary CH refined with riding coordinates:
 C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C1(H1A,H1B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C3(H3)
3.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.99567(7) 0.2888(5) 0.36014(6) 0.0378(2) Uani 1 1 d . . . . .
S1 S 1.4619(3) 0.4045(9) 0.6795(3) 0.1051(12) Uani 1 1 d . . . . .
O2 O 1.0198(4) 0.0378(11) 0.4687(4) 0.0425(12) Uani 1 1 d . . . . .
O4 O 0.8954(5) 0.9983(5) 0.2453(4) 0.0510(13) Uani 1 1 d D . . . .
O3 O 0.9822(5) 0.5474(11) 0.2615(4) 0.0470(13) Uani 1 1 d . . . . .
O1 O 1.1626(4) -0.1324(10) 0.5893(4) 0.0446(14) Uani 1 1 d . . . . .
N1 N 1.1688(5) 0.2357(12) 0.3590(5) 0.0382(17) Uani 1 1 d . . . . .
C11 C 1.2276(6) 0.0586(16) 0.4384(6) 0.0442(18) Uani 1 1 d . . . . .
H11 H 1.248340 -0.081088 0.398863 0.053 Uiso 1 1 calc R U . . .
C4 C 1.2388(7) 0.795(3) 0.0846(5) 0.0570(18) Uani 1 1 d . . . . .
C6 C 1.2666(7) 0.6084(17) 0.1522(6) 0.0518(19) Uani 1 1 d . . . . .
H6 H 1.342447 0.536469 0.156743 0.062 Uiso 1 1 calc R U . . .
C10 C 1.1303(6) -0.0176(15) 0.5037(6) 0.0386(16) Uani 1 1 d . . . . .
C2 C 1.0414(7) 0.8263(19) 0.1430(6) 0.046(2) Uani 1 1 d . . . . .
C9 C 1.2302(6) 0.3310(16) 0.2918(5) 0.044(2) Uani 1 1 d . . . . .
H9 H 1.308723 0.275333 0.292184 0.052 Uiso 1 1 calc R U . . .
C7 C 1.1848(6) 0.5170(15) 0.2169(6) 0.0441(17) Uani 1 1 d . . . . .
C12 C 1.3447(7) 0.1442(18) 0.5118(7) 0.057(2) Uani 1 1 d . . . . .
H12A H 1.378297 0.013502 0.557872 0.068 Uiso 1 1 calc R U . . .
H12B H 1.404016 0.186987 0.467763 0.068 Uiso 1 1 calc R U . . .
C1 C 0.9208(8) 0.9503(18) 0.1394(6) 0.059(2) Uani 1 1 d . . . . .
H1A H 0.921248 1.099371 0.100713 0.071 Uiso 1 1 calc R U . . .
H1B H 0.856295 0.851625 0.100401 0.071 Uiso 1 1 calc R U . . .
C8 C 1.0685(7) 0.6229(15) 0.2097(6) 0.0427(17) Uani 1 1 d . . . . .
C3 C 1.1245(8) 0.9095(17) 0.0835(6) 0.055(2) Uani 1 1 d . . . . .
H3 H 1.105423 1.044491 0.041234 0.067 Uiso 1 1 calc R U . . .
C5 C 1.3253(11) 0.889(2) 0.0120(9) 0.090(4) Uani 1 1 d . . . . .
H5A H 1.404194 0.817633 0.033231 0.134 Uiso 1 1 calc R U . . .
H5B H 1.332087 1.058541 0.018607 0.134 Uiso 1 1 calc R U . . .
H5C H 1.293448 0.847467 -0.061244 0.134 Uiso 1 1 calc R U . . .
C13 C 1.3262(8) 0.350(2) 0.5795(10) 0.079(4) Uani 1 1 d . . . . .
H13A H 1.257629 0.319322 0.615024 0.095 Uiso 1 1 calc R U . . .
H13B H 1.307551 0.490342 0.534913 0.095 Uiso 1 1 calc R U . . .
C14 C 1.4110(14) 0.615(4) 0.7639(13) 0.144(7) Uani 1 1 d . . . . .
H14A H 1.359406 0.729265 0.721284 0.215 Uiso 1 1 calc R U . . .
H14B H 1.479836 0.695671 0.805109 0.215 Uiso 1 1 calc R U . . .
H14C H 1.366062 0.536162 0.811499 0.215 Uiso 1 1 calc R U . . .
H4 H 0.915(8) 0.827(6) 0.277(6) 0.10(3) Uiso 1 1 d D . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O4 85.7(2) . 1_545 ?
O2 Cu1 O1 87.3(2) . 2_756 ?
O2 Cu1 N1 83.4(2) . . ?
O3 Cu1 O2 175.4(3) . . ?
O3 Cu1 O4 98.7(2) . 1_545 ?
O3 Cu1 O1 94.0(2) . 2_756 ?
O3 Cu1 N1 94.2(2) . . ?
O1 Cu1 O4 90.11(19) 2_756 1_545 ?
N1 Cu1 O4 104.6(2) . 1_545 ?
N1 Cu1 O1 161.8(2) . 2_756 ?
C14 S1 C13 102.6(6) . . ?
C10 O2 Cu1 115.1(4) . . ?
Cu1 O4 H4 111(4) 1_565 . ?
C1 O4 Cu1 123.8(5) . 1_565 ?
C1 O4 H4 97(4) . . ?
C8 O3 Cu1 126.1(5) . . ?
C10 O1 Cu1 104.6(4) . 2_746 ?
C11 N1 Cu1 114.5(4) . . ?
C9 N1 Cu1 125.4(5) . . ?
C9 N1 C11 120.0(6) . . ?
N1 C11 H11 107.9 . . ?
N1 C11 C10 106.4(5) . . ?
N1 C11 C12 115.2(6) . . ?
C10 C11 H11 107.9 . . ?
C12 C11 H11 107.9 . . ?
C12 C11 C10 111.5(6) . . ?
C6 C4 C3 117.3(7) . . ?
C6 C4 C5 122.9(9) . . ?
C3 C4 C5 119.8(10) . . ?
C4 C6 H6 118.5 . . ?
C4 C6 C7 122.9(7) . . ?
C7 C6 H6 118.5 . . ?
O2 C10 C11 118.6(6) . . ?
O1 C10 O2 122.4(6) . . ?
O1 C10 C11 119.0(6) . . ?
C8 C2 C1 118.9(7) . . ?
C3 C2 C1 120.7(9) . . ?
C3 C2 C8 120.4(8) . . ?
N1 C9 H9 117.8 . . ?
N1 C9 C7 124.5(6) . . ?
C7 C9 H9 117.8 . . ?
C6 C7 C9 117.0(7) . . ?
C8 C7 C6 119.1(7) . . ?
C8 C7 C9 123.8(6) . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C11 113.8(7) . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
O4 C1 C2 112.3(6) . . ?
O4 C1 H1A 109.1 . . ?
O4 C1 H1B 109.1 . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
O3 C8 C2 117.1(6) . . ?
O3 C8 C7 124.8(7) . . ?
C7 C8 C2 118.1(6) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 C4 122.1(9) . . ?
C2 C3 H3 119.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
S1 C13 H13A 109.5 . . ?
S1 C13 H13B 109.5 . . ?
C12 C13 S1 110.5(6) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.954(5) . ?
Cu1 O4 2.333(6) 1_545 ?
Cu1 O3 1.904(5) . ?
Cu1 O1 2.033(5) 2_756 ?
Cu1 N1 1.957(5) . ?
S1 C13 1.818(10) . ?
S1 C14 1.756(18) . ?
O2 C10 1.272(8) . ?
O4 C1 1.447(9) . ?
O4 H4 1.0540(14) . ?
O3 C8 1.329(9) . ?
O1 C10 1.258(9) . ?
N1 C11 1.482(9) . ?
N1 C9 1.299(9) . ?
C11 H11 0.9800 . ?
C11 C10 1.540(9) . ?
C11 C12 1.539(12) . ?
C4 C6 1.356(14) . ?
C4 C3 1.425(13) . ?
C4 C5 1.540(11) . ?
C6 H6 0.9300 . ?
C6 C7 1.427(10) . ?
C2 C1 1.509(12) . ?
C2 C8 1.420(12) . ?
C2 C3 1.378(11) . ?
C9 H9 0.9300 . ?
C9 C7 1.441(11) . ?
C7 C8 1.416(11) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.476(13) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 H3 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O2 C10 O1 163.1(6) . . . . ?
Cu1 O2 C10 C11 -17.1(9) . . . . ?
Cu1 O4 C1 C2 72.3(9) 1_565 . . . ?
Cu1 O3 C8 C2 -177.3(5) . . . . ?
Cu1 O3 C8 C7 2.2(10) . . . . ?
Cu1 O1 C10 O2 3.7(8) 2_746 . . . ?
Cu1 O1 C10 C11 -176.1(5) 2_746 . . . ?
Cu1 N1 C11 C10 -3.7(7) . . . . ?
Cu1 N1 C11 C12 -127.7(6) . . . . ?
Cu1 N1 C9 C7 9.2(12) . . . . ?
N1 C11 C10 O2 13.5(9) . . . . ?
N1 C11 C10 O1 -166.7(7) . . . . ?
N1 C11 C12 C13 61.6(9) . . . . ?
N1 C9 C7 C6 177.3(8) . . . . ?
N1 C9 C7 C8 1.9(13) . . . . ?
C11 N1 C9 C7 -175.3(7) . . . . ?
C11 C12 C13 S1 169.9(6) . . . . ?
C4 C6 C7 C9 -174.8(9) . . . . ?
C4 C6 C7 C8 0.8(12) . . . . ?
C6 C4 C3 C2 -4.1(14) . . . . ?
C6 C7 C8 O3 176.6(7) . . . . ?
C6 C7 C8 C2 -3.9(11) . . . . ?
C10 C11 C12 C13 -59.7(9) . . . . ?
C9 N1 C11 C10 -179.7(7) . . . . ?
C9 N1 C11 C12 56.3(9) . . . . ?
C9 C7 C8 O3 -8.1(12) . . . . ?
C9 C7 C8 C2 171.4(8) . . . . ?
C12 C11 C10 O2 139.8(7) . . . . ?
C12 C11 C10 O1 -40.4(10) . . . . ?
C1 C2 C8 O3 3.1(11) . . . . ?
C1 C2 C8 C7 -176.4(7) . . . . ?
C1 C2 C3 C4 -179.5(8) . . . . ?
C8 C2 C1 O4 49.2(11) . . . . ?
C8 C2 C3 C4 1.0(13) . . . . ?
C3 C4 C6 C7 3.1(14) . . . . ?
C3 C2 C1 O4 -130.3(8) . . . . ?
C3 C2 C8 O3 -177.5(7) . . . . ?
C3 C2 C8 C7 3.0(11) . . . . ?
C5 C4 C6 C7 -177.8(9) . . . . ?
C5 C4 C3 C2 176.8(9) . . . . ?
C14 S1 C13 C12 -169.8(9) . . . . ?
