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#$Date: 2025-04-05 06:46:22 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299022 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/36/7063685.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_7063685
loop_
_publ_author_name
'Manurkar, Nagesh'
'Ilyas, Mubashar'
'Arshad, Faiza'
'Patil, Prasanna'
'Shah, Haroon'
'Khan, Maroof Ahmad'
'Hussain, Wajid'
'Li, Hui'
_publ_section_title
;
 Exploring the first and second hyperpolarizabilities of l-glutamine-based
 Schiff base ligands and their Cu(ii) coordination complexes
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5200
_journal_page_last               5212
_journal_paper_doi               10.1039/D5NJ00477B
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C24 H28 Cu2 F2 N4 O11, 2(H2 O)'
_chemical_formula_sum            'C24 H32 Cu2 F2 N4 O13'
_chemical_formula_weight         749.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2jnmtn
_audit_creation_date             2024-03-27
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-26 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.362(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.460(2)
_cell_length_b                   11.1429(8)
_cell_length_c                   11.7925(9)
_cell_measurement_reflns_used    3969
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.51
_cell_volume                     2854.5(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.792
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.792
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6479
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.792
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.712
_diffrn_reflns_theta_min         2.054
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.578
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0541 before and 0.0382 after correction.
The Ratio of minimum to maximum transmission is 0.9207.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear bluish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3827
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0446
_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/[σ²(Fo²)+(0.0465P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1078
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2372
_reflns_number_total             3827
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5nj00477b2.cif
_cod_data_source_block           n
_cod_depositor_comments
'Adding full bibliography for 7063685--7063686.cif.'
_cod_original_cell_volume        2854.6(4)
_cod_database_code               7063685
_shelx_shelxl_version_number     2019/3
_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.
;
_shelx_estimated_absorpt_t_max   0.743
_shelx_estimated_absorpt_t_min   0.703
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 Cu1-H5A \\sim Cu1-H5B
 with sigma of 0.02
3. Others
 Fixed Sof: H6A(0.5) H6B(0.5)
4.a Free rotating group:
 O2(H2E,H2F), O5(H5A,H5B)
4.b Rotating group:
 O6(H6A,H6B)
4.c Ternary CH refined with riding coordinates:
 C8(H8)
4.d Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C2(H2C,H2D)
4.e Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C11(H11)
4.f X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.40557(2) 0.28872(3) 0.56959(4) 0.02780(13) Uani 1 1 d D . . . .
O1 O 0.36696(10) 0.23117(17) 0.6684(2) 0.0329(5) Uani 1 1 d . . . . .
O4 O 0.43237(11) 0.34304(19) 0.4458(2) 0.0342(5) Uani 1 1 d . . . . .
O6 O 0.500000 0.3579(2) 0.750000 0.0319(7) Uani 1 2 d S T P . .
H6A H 0.519250 0.403936 0.723020 0.048 Uiso 0.5 1 d R U P . .
H6B H 0.490910 0.402599 0.797359 0.048 Uiso 0.5 1 d R U P . .
O7 O 0.43295(12) 0.50005(19) 0.3306(2) 0.0423(6) Uani 1 1 d . . . . .
O2 O 0.55843(12) 0.0907(2) 0.6333(3) 0.0411(6) Uani 1 1 d G . . . .
H2E H 0.581775 0.138400 0.691779 0.062 Uiso 1 1 d G U . . .
H2F H 0.562852 0.110642 0.568421 0.062 Uiso 1 1 d G U . . .
O5 O 0.44203(11) 0.13190(18) 0.5768(3) 0.0457(7) Uani 1 1 d G . . . .
H5A H 0.480150 0.119241 0.602149 0.068 Uiso 1 1 d DG U . . .
H5B H 0.428030 0.064770 0.585987 0.068 Uiso 1 1 d DG U . . .
N1 N 0.35914(12) 0.43637(19) 0.5233(2) 0.0245(6) Uani 1 1 d . . . . .
O3 O 0.40662(13) 0.90147(19) 0.5642(2) 0.0457(7) Uani 1 1 d . . . . .
F1 F 0.21677(12) 0.1952(2) 0.8056(3) 0.0769(8) Uani 1 1 d . . . . .
N2 N 0.42951(14) 0.8378(2) 0.7613(3) 0.0447(8) Uani 1 1 d . . . . .
H2A H 0.444422 0.906405 0.794650 0.054 Uiso 1 1 calc R U . . .
H2B H 0.429095 0.779765 0.808997 0.054 Uiso 1 1 calc R U . . .
C1 C 0.31734(14) 0.2755(3) 0.6675(3) 0.0277(7) Uani 1 1 d . . . . .
C4 C 0.28676(14) 0.3804(3) 0.6011(3) 0.0269(7) Uani 1 1 d . . . . .
C6 C 0.30934(15) 0.4540(3) 0.5308(3) 0.0293(7) Uani 1 1 d . . . . .
H6 H 0.285584 0.519869 0.487316 0.035 Uiso 1 1 calc R U . . .
C8 C 0.37796(15) 0.5203(3) 0.4511(3) 0.0308(7) Uani 1 1 d . . . . .
H8 H 0.341111 0.549149 0.376514 0.037 Uiso 1 1 calc R U . . .
C10 C 0.41819(15) 0.4502(3) 0.4051(3) 0.0312(7) Uani 1 1 d . . . . .
C12 C 0.41388(16) 0.6285(3) 0.5305(3) 0.0358(8) Uani 1 1 d . . . . .
H12A H 0.451952 0.600322 0.600507 0.043 Uiso 1 1 calc R U . . .
H12B H 0.424545 0.680210 0.477450 0.043 Uiso 1 1 calc R U . . .
C3 C 0.40731(16) 0.8217(3) 0.6375(3) 0.0333(8) Uani 1 1 d . . . . .
C7 C 0.29149(15) 0.2138(3) 0.7361(3) 0.0373(8) Uani 1 1 d . . . . .
H7 H 0.309812 0.144030 0.780654 0.045 Uiso 1 1 calc R U . . .
C2 C 0.37889(16) 0.7014(3) 0.5843(3) 0.0369(8) Uani 1 1 d . . . . .
H2C H 0.337242 0.713991 0.517445 0.044 Uiso 1 1 calc R U . . .
H2D H 0.376318 0.655442 0.651585 0.044 Uiso 1 1 calc R U . . .
C9 C 0.23240(16) 0.4178(3) 0.6034(3) 0.0372(8) Uani 1 1 d . . . . .
H9 H 0.212148 0.485608 0.557176 0.045 Uiso 1 1 calc R U . . .
C5 C 0.23909(17) 0.2577(3) 0.7363(4) 0.0430(9) Uani 1 1 d . . . . .
C11 C 0.20813(17) 0.3573(3) 0.6719(4) 0.0466(10) Uani 1 1 d . . . . .
H11 H 0.172457 0.383236 0.673965 0.056 Uiso 1 1 calc R U . . .
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'
F F 0.0171 0.0103 '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'
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
O1 Cu1 O4 171.00(10) . . ?
O1 Cu1 O6 96.28(7) . . ?
O1 Cu1 O5 90.96(9) . . ?
O1 Cu1 N1 93.85(9) . . ?
O4 Cu1 O6 92.60(7) . . ?
O5 Cu1 O4 90.37(10) . . ?
O5 Cu1 O6 90.83(10) . . ?
N1 Cu1 O4 83.11(9) . . ?
N1 Cu1 O6 100.12(9) . . ?
N1 Cu1 O5 167.47(12) . . ?
C1 O1 Cu1 125.77(19) . . ?
C10 O4 Cu1 116.47(18) . . ?
Cu1 O6 H6A 109.3 . . ?
Cu1 O6 H6A 93(3) . 2_656 ?
Cu1 O6 H6B 109.2 . . ?
Cu1 O6 H6B 92(3) . 2_656 ?
H6A O6 H6A 105.9 . 2_656 ?
H6A O6 H6B 104.5 2_656 2_656 ?
H6A O6 H6B 104.5 . . ?
H6A O6 H6B 17.2 . 2_656 ?
H6B O6 H6A 17.2 . 2_656 ?
H6B O6 H6B 108.4 . 2_656 ?
H2E O2 H2F 104.5 . . ?
Cu1 O5 H5A 124.8 . . ?
Cu1 O5 H5B 126.3 . . ?
H5A O5 H5B 104.5 . . ?
C6 N1 Cu1 124.6(2) . . ?
C6 N1 C8 120.2(3) . . ?
C8 N1 Cu1 113.92(18) . . ?
H2A N2 H2B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
O1 C1 C4 124.7(3) . . ?
O1 C1 C7 118.0(3) . . ?
C7 C1 C4 117.2(3) . . ?
C1 C4 C6 122.9(3) . . ?
C9 C4 C1 119.9(3) . . ?
C9 C4 C6 117.2(3) . . ?
N1 C6 C4 125.5(3) . . ?
N1 C6 H6 117.2 . . ?
C4 C6 H6 117.2 . . ?
N1 C8 H8 108.9 . . ?
N1 C8 C10 107.5(2) . . ?
N1 C8 C12 113.0(2) . . ?
C10 C8 H8 108.9 . . ?
C12 C8 H8 108.9 . . ?
C12 C8 C10 109.6(3) . . ?
O4 C10 C8 116.8(3) . . ?
O7 C10 O4 125.2(3) . . ?
O7 C10 C8 118.0(3) . . ?
C8 C12 H12A 108.8 . . ?
C8 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C2 C12 C8 113.7(3) . . ?
C2 C12 H12A 108.8 . . ?
C2 C12 H12B 108.8 . . ?
O3 C3 N2 123.0(3) . . ?
O3 C3 C2 119.6(3) . . ?
N2 C3 C2 117.3(3) . . ?
C1 C7 H7 120.3 . . ?
C5 C7 C1 119.5(3) . . ?
C5 C7 H7 120.3 . . ?
C12 C2 H2C 108.7 . . ?
C12 C2 H2D 108.7 . . ?
C3 C2 C12 114.2(3) . . ?
C3 C2 H2C 108.7 . . ?
C3 C2 H2D 108.7 . . ?
H2C C2 H2D 107.6 . . ?
C4 C9 H9 118.9 . . ?
C11 C9 C4 122.2(3) . . ?
C11 C9 H9 118.9 . . ?
F1 C5 C7 116.8(3) . . ?
C11 C5 F1 118.5(3) . . ?
C11 C5 C7 124.7(3) . . ?
C9 C11 H11 121.7 . . ?
C5 C11 C9 116.5(3) . . ?
C5 C11 H11 121.7 . . ?
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 O1 1.916(2) . ?
Cu1 O4 1.951(2) . ?
Cu1 O6 2.4371(10) . ?
Cu1 O5 1.946(2) . ?
Cu1 N1 1.930(2) . ?
O1 C1 1.306(3) . ?
O4 C10 1.274(4) . ?
O6 H6A 0.8504 . ?
O6 H6A 0.85(10) 2_656 ?
O6 H6B 0.85(10) 2_656 ?
O6 H6B 0.8503 . ?
O7 C10 1.226(3) . ?
O2 H2E 0.8495 . ?
O2 H2F 0.8501 . ?
O5 H5A 0.8500 . ?
O5 H5B 0.8500 . ?
N1 C6 1.277(4) . ?
N1 C8 1.474(3) . ?
O3 C3 1.234(4) . ?
F1 C5 1.363(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C3 1.316(4) . ?
C1 C4 1.414(4) . ?
C1 C7 1.413(4) . ?
C4 C6 1.444(4) . ?
C4 C9 1.406(4) . ?
C6 H6 0.9300 . ?
C8 H8 0.9800 . ?
C8 C10 1.538(4) . ?
C8 C12 1.531(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C2 1.516(4) . ?
C3 C2 1.507(4) . ?
C7 H7 0.9300 . ?
C7 C5 1.373(5) . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C9 H9 0.9300 . ?
C9 C11 1.378(4) . ?
C5 C11 1.362(5) . ?
C11 H11 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O6 H6A O7 0.85 1.90 2.744(3) 176.1 5_666 yes
O6 H6B O7 0.85 1.96 2.744(3) 152.3 6_566 yes
O2 H2E O1 0.85 1.86 2.707(3) 174.2 2_656 yes
O2 H2F O3 0.85 2.02 2.827(3) 157.4 5_666 yes
O5 H5A O2 0.85 1.80 2.649(3) 172.2 . yes
O5 H5B O3 0.85 1.88 2.692(3) 159.8 1_545 yes
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 O1 C1 C4 -5.7(4) . . . . ?
Cu1 O1 C1 C7 173.3(2) . . . . ?
Cu1 O4 C10 O7 177.5(3) . . . . ?
Cu1 O4 C10 C8 -4.2(4) . . . . ?
Cu1 N1 C6 C4 15.3(4) . . . . ?
Cu1 N1 C8 C10 14.4(3) . . . . ?
Cu1 N1 C8 C12 -106.7(2) . . . . ?
O1 C1 C4 C6 -3.1(5) . . . . ?
O1 C1 C4 C9 177.9(3) . . . . ?
O1 C1 C7 C5 -179.6(3) . . . . ?
N1 C8 C10 O4 -6.6(4) . . . . ?
N1 C8 C10 O7 171.8(3) . . . . ?
N1 C8 C12 C2 -58.1(4) . . . . ?
O3 C3 C2 C12 69.2(4) . . . . ?
F1 C5 C11 C9 179.9(3) . . . . ?
N2 C3 C2 C12 -113.7(3) . . . . ?
C1 C4 C6 N1 -2.2(5) . . . . ?
C1 C4 C9 C11 1.9(5) . . . . ?
C1 C7 C5 F1 -179.2(3) . . . . ?
C1 C7 C5 C11 1.5(6) . . . . ?
C4 C1 C7 C5 -0.5(5) . . . . ?
C4 C9 C11 C5 -0.9(5) . . . . ?
C6 N1 C8 C10 -153.4(3) . . . . ?
C6 N1 C8 C12 85.5(4) . . . . ?
C6 C4 C9 C11 -177.2(3) . . . . ?
C8 N1 C6 C4 -178.3(3) . . . . ?
C8 C12 C2 C3 -167.3(3) . . . . ?
C10 C8 C12 C2 -178.0(3) . . . . ?
C12 C8 C10 O4 116.5(3) . . . . ?
C12 C8 C10 O7 -65.0(4) . . . . ?
C7 C1 C4 C6 177.9(3) . . . . ?
C7 C1 C4 C9 -1.1(4) . . . . ?
C7 C5 C11 C9 -0.8(6) . . . . ?
C9 C4 C6 N1 176.8(3) . . . . ?
