#------------------------------------------------------------------------------
#$Date: 2017-06-16 05:09:36 +0300 (Fri, 16 Jun 2017) $
#$Revision: 197875 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/33/7043333.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_7043333
loop_
_publ_author_name
'Sama, Farasha'
'Dhara, Ashish Kumar'
'Akhtar, Muammad Nadeem'
'Chen, Yan-Cong'
'Tong, Mingliang'
'Shahid, M.'
'Ansari, Istikhar A.'
'Raizada, Mukul'
'Ahmad, Musheer'
'Siddiqi, Zafar A.'
_publ_section_title
;
 Amino alcohols and benzoates-Friends or foes? Tuning nuclearity of Cu(II)
 complexes, structures, magnetism, DFT and TD-DFT studies, and catecholase
 like activities
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT01571B
_journal_year                    2017
_chemical_formula_moiety         'C13 H19 Cu N O6, H2 O'
_chemical_formula_sum            'C13 H21 Cu N O7'
_chemical_formula_weight         366.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-06-06 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.877(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.682(5)
_cell_length_b                   26.946(5)
_cell_length_c                   8.247(5)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.45
_cell_volume                     1561.0(14)
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'BRUKER SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10742
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         3.096
_exptl_absorpt_coefficient_mu    1.432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_description       Block
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.250
_exptl_transmission_factor_max   0.699
_exptl_transmission_factor_min   0.676
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4146
_refine_ls_number_restraints     91
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0384
_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)+(0.0528P)²+0.4321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1112
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3761
_reflns_number_total             4146
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt01571b2.cif
_cod_data_source_block           complex5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7043333
_shelx_shelxl_version_number     2016/6
_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_min   0.690
_shelx_estimated_absorpt_t_max   0.716
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.51069(3) 0.44628(2) 0.49212(3) 0.02934(10) Uani 1 1 d . . . . .
O1A O 0.9853(9) 0.3559(3) 0.6785(9) 0.0539(19) Uani 0.310(5) 1 d . . P A 2
H1H1 H 0.996646 0.384835 0.712019 0.081 Uiso 0.310(5) 1 calc R U P A 2
O1 O 0.6980(5) 0.28929(13) 1.0094(4) 0.0669(10) Uani 0.690(5) 1 d . . P A 1
H1 H 0.623398 0.312435 0.969941 0.100 Uiso 0.690(5) 1 calc R U P A 1
O2 O 0.5292(3) 0.36092(8) 0.7975(2) 0.0537(4) Uani 1 1 d . . . . .
O3 O 0.6775(2) 0.39348(6) 0.6388(2) 0.0411(4) Uani 1 1 d . . . . .
O4 O 0.2451(2) 0.41304(7) 0.5652(2) 0.0485(4) Uani 1 1 d . . . . .
H4 H 0.315302 0.394866 0.644428 0.073 Uiso 1 1 calc R U . . .
O5 O 0.3470(2) 0.49996(5) 0.3563(2) 0.0333(3) Uani 1 1 d . . . . .
O6 O 0.7264(3) 0.44468(7) 0.3352(2) 0.0501(4) Uani 1 1 d . . . . .
H6 H 0.792775 0.466073 0.317645 0.075 Uiso 1 1 calc R U . . .
N1 N 0.3674(2) 0.40412(6) 0.2724(2) 0.0327(4) Uani 1 1 d . . . . .
C1 C 0.809(3) 0.3260(10) 0.847(4) 0.031(3) Uani 0.310(5) 1 d . . P A 2
C1A C 0.8410(14) 0.3303(4) 0.8334(16) 0.0304(15) Uani 0.690(5) 1 d . . P A 1
C2 C 0.805(3) 0.2950(10) 0.982(3) 0.047(4) Uani 0.310(5) 1 d . . P A 2
H2 H 0.708999 0.298155 1.023411 0.057 Uiso 0.310(5) 1 calc R U P A 2
C2A C 0.8377(12) 0.2934(4) 0.9544(11) 0.0381(14) Uani 0.690(5) 1 d . . P A 1
C3 C 0.938(3) 0.2616(11) 1.048(4) 0.061(4) Uani 0.310(5) 1 d . . P A 2
H3 H 0.930077 0.239671 1.132099 0.074 Uiso 0.310(5) 1 calc R U P A 2
C3A C 0.9909(11) 0.2596(3) 1.0251(12) 0.0519(18) Uani 0.690(5) 1 d . . P A 1
H3A H 0.993204 0.236138 1.108532 0.062 Uiso 0.690(5) 1 calc R U P A 1
C4 C 1.087(3) 0.2571(8) 1.000(3) 0.056(5) Uani 0.310(5) 1 d . . P A 2
H4A H 1.173761 0.231561 1.049563 0.068 Uiso 0.310(5) 1 calc R U P A 2
C4A C 1.1360(12) 0.2620(4) 0.9693(14) 0.0557(18) Uani 0.690(5) 1 d . . P A 1
H4AA H 1.235742 0.239403 1.013629 0.067 Uiso 0.690(5) 1 calc R U P A 1
C5 C 1.115(4) 0.2888(10) 0.881(4) 0.054(4) Uani 0.310(5) 1 d . . P A 2
H5 H 1.220401 0.287106 0.853436 0.064 Uiso 0.310(5) 1 calc R U P A 2
C5A C 1.1369(15) 0.2978(4) 0.8467(17) 0.0545(18) Uani 0.690(5) 1 d . . P A 1
H5A H 1.236848 0.298857 0.810518 0.065 Uiso 0.690(5) 1 calc R U P A 1
C6 C 0.960(3) 0.3260(9) 0.802(3) 0.035(3) Uani 0.310(5) 1 d . . P A 2
C6A C 0.9923(14) 0.3311(4) 0.7805(15) 0.0380(15) Uani 0.690(5) 1 d . . P A 1
H6A H 0.994041 0.354740 0.698969 0.046 Uiso 0.690(5) 1 calc R U P A 1
C7 C 0.6671(3) 0.36378(8) 0.7530(3) 0.0379(5) Uani 1 1 d . . . . .
C8 C 0.2593(3) 0.36497(9) 0.3180(3) 0.0428(5) Uani 1 1 d . . . . .
H8A H 0.348175 0.340463 0.392618 0.051 Uiso 1 1 calc R U . . .
H8B H 0.175931 0.348450 0.209904 0.051 Uiso 1 1 calc R U . . .
C9 C 0.1412(3) 0.38430(12) 0.4128(4) 0.0547(6) Uani 1 1 d . . . . .
H9A H 0.038469 0.404364 0.330729 0.066 Uiso 1 1 calc R U . . .
H9B H 0.084515 0.356340 0.447553 0.066 Uiso 1 1 calc R U . . .
C10 C 0.2366(3) 0.43833(8) 0.1332(3) 0.0415(5) Uani 1 1 d . . . . .
H10A H 0.108487 0.434971 0.127275 0.050 Uiso 1 1 calc R U . . .
H10B H 0.234349 0.429204 0.018548 0.050 Uiso 1 1 calc R U . . .
C11 C 0.3013(3) 0.49189(8) 0.1742(3) 0.0383(5) Uani 1 1 d . . . . .
H11A H 0.411882 0.497884 0.148285 0.046 Uiso 1 1 calc R U . . .
H11B H 0.200441 0.514231 0.102568 0.046 Uiso 1 1 calc R U . . .
C12 C 0.5049(3) 0.37973(9) 0.2125(3) 0.0423(5) Uani 1 1 d . . . . .
H12A H 0.434818 0.361411 0.104292 0.051 Uiso 1 1 calc R U . . .
H12B H 0.580923 0.356158 0.302039 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6354(4) 0.41629(10) 0.1791(3) 0.0488(6) Uani 1 1 d . . . . .
H13A H 0.729391 0.398802 0.150051 0.059 Uiso 1 1 calc R U . . .
H13B H 0.562799 0.437806 0.080527 0.059 Uiso 1 1 calc R U . . .
O1W O 0.0572(3) 0.48162(8) 0.7107(2) 0.0512(4) Uani 1 1 d G . . . .
H1WA H -0.062423 0.486256 0.669626 0.077 Uiso 1 1 d DG U . . .
H1WB H 0.080902 0.456643 0.659908 0.077 Uiso 1 1 d G 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'
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
O5 Cu1 O5 83.10(7) 3_666 .
O5 Cu1 O3 94.99(7) 3_666 .
O5 Cu1 O3 177.57(6) . .
O5 Cu1 N1 161.72(8) 3_666 .
O5 Cu1 N1 84.96(7) . .
O3 Cu1 N1 97.25(7) . .
C6 O1A H1H1 109.5 . .
C2A O1 H1 109.5 . .
C7 O3 Cu1 133.98(16) . .
C9 O4 H4 109.5 . .
C11 O5 Cu1 129.30(14) . 3_666
C11 O5 Cu1 108.77(12) . .
Cu1 O5 Cu1 96.90(7) 3_666 .
C13 O6 H6 109.5 . .
C8 N1 C12 108.40(17) . .
C8 N1 C10 111.21(17) . .
C12 N1 C10 111.30(18) . .
C8 N1 Cu1 109.08(14) . .
C12 N1 Cu1 109.89(13) . .
C10 N1 Cu1 106.94(13) . .
C6 C1 C2 121(2) . .
C6 C1 C7 113.1(16) . .
C2 C1 C7 125.6(17) . .
C6A C1A C2A 119.1(7) . .
C6A C1A C7 123.2(7) . .
C2A C1A C7 117.3(6) . .
C3 C2 C1 118.3(18) . .
C3 C2 H2 120.8 . .
C1 C2 H2 120.8 . .
O1 C2A C3A 117.3(7) . .
O1 C2A C1A 123.2(7) . .
C3A C2A C1A 119.5(7) . .
C2 C3 C4 123(2) . .
C2 C3 H3 118.3 . .
C4 C3 H3 118.3 . .
C4A C3A C2A 119.2(6) . .
C4A C3A H3A 120.4 . .
C2A C3A H3A 120.4 . .
C3 C4 C5 122.8(18) . .
C3 C4 H4A 118.6 . .
C5 C4 H4A 118.6 . .
C3A C4A C5A 121.2(6) . .
C3A C4A H4AA 119.4 . .
C5A C4A H4AA 119.4 . .
C4 C5 C6 113.6(16) . .
C4 C5 H5 123.2 . .
C6 C5 H5 123.2 . .
C6A C5A C4A 120.2(7) . .
C6A C5A H5A 119.9 . .
C4A C5A H5A 119.9 . .
C1 C6 O1A 126.8(18) . .
C1 C6 C5 120.2(16) . .
O1A C6 C5 112.9(13) . .
C5A C6A C1A 120.8(7) . .
C5A C6A H6A 119.6 . .
C1A C6A H6A 119.6 . .
O2 C7 O3 124.9(2) . .
O2 C7 C1 109.8(7) . .
O3 C7 C1 125.3(7) . .
O2 C7 C1A 122.1(3) . .
O3 C7 C1A 113.0(3) . .
N1 C8 C9 113.7(2) . .
N1 C8 H8A 108.8 . .
C9 C8 H8A 108.8 . .
N1 C8 H8B 108.8 . .
C9 C8 H8B 108.8 . .
H8A C8 H8B 107.7 . .
O4 C9 C8 114.1(2) . .
O4 C9 H9A 108.7 . .
C8 C9 H9A 108.7 . .
O4 C9 H9B 108.7 . .
C8 C9 H9B 108.7 . .
H9A C9 H9B 107.6 . .
N1 C10 C11 110.89(16) . .
N1 C10 H10A 109.5 . .
C11 C10 H10A 109.5 . .
N1 C10 H10B 109.5 . .
C11 C10 H10B 109.5 . .
H10A C10 H10B 108.1 . .
O5 C11 C10 107.52(18) . .
O5 C11 H11A 110.2 . .
C10 C11 H11A 110.2 . .
O5 C11 H11B 110.2 . .
C10 C11 H11B 110.2 . .
H11A C11 H11B 108.5 . .
N1 C12 C13 112.69(19) . .
N1 C12 H12A 109.1 . .
C13 C12 H12A 109.1 . .
N1 C12 H12B 109.1 . .
C13 C12 H12B 109.1 . .
H12A C12 H12B 107.8 . .
O6 C13 C12 107.9(2) . .
O6 C13 H13A 110.1 . .
C12 C13 H13A 110.1 . .
O6 C13 H13B 110.1 . .
C12 C13 H13B 110.1 . .
H13A C13 H13B 108.4 . .
H1WA O1W H1WB 109.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O5 1.9365(15) 3_666
Cu1 O5 1.9464(15) .
Cu1 O3 1.9683(15) .
Cu1 N1 2.0422(18) .
O1A C6 1.376(15) .
O1A H1H1 0.8200 .
O1 C2A 1.327(7) .
O1 H1 0.8200 .
O2 C7 1.257(3) .
O3 C7 1.263(3) .
O4 C9 1.416(3) .
O4 H4 0.8200 .
O5 C11 1.414(3) .
O6 C13 1.415(3) .
O6 H6 0.8200 .
N1 C8 1.482(3) .
N1 C12 1.488(3) .
N1 C10 1.498(3) .
C1 C6 1.349(17) .
C1 C2 1.40(2) .
C1 C7 1.46(3) .
C1A C6A 1.397(7) .
C1A C2A 1.417(9) .
C1A C7 1.524(10) .
C2 C3 1.30(3) .
C2 H2 0.9300 .
C2A C3A 1.413(9) .
C3 C4 1.36(2) .
C3 H3 0.9300 .
C3A C4A 1.368(8) .
C3A H3A 0.9300 .
C4 C5 1.380(19) .
C4 H4A 0.9300 .
C4A C5A 1.400(9) .
C4A H4AA 0.9300 .
C5 C6 1.49(3) .
C5 H5 0.9300 .
C5A C6A 1.358(12) .
C5A H5A 0.9300 .
C6A H6A 0.9300 .
C8 C9 1.509(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.519(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.509(4) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
O1W H1WA 0.8499 .
O1W H1WB 0.8507 .
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
C6 C1 C2 C3 -9(5) .
C7 C1 C2 C3 177(3) .
C6A C1A C2A O1 -178.8(10) .
C7 C1A C2A O1 -5.0(16) .
C6A C1A C2A C3A 2.8(17) .
C7 C1A C2A C3A 176.6(9) .
C1 C2 C3 C4 4(5) .
O1 C2A C3A C4A 178.7(8) .
C1A C2A C3A C4A -2.7(15) .
C2 C3 C4 C5 2(5) .
C2A C3A C4A C5A 1.4(15) .
C3 C4 C5 C6 -4(4) .
C3A C4A C5A C6A -0.1(19) .
C2 C1 C6 O1A -177(3) .
C7 C1 C6 O1A -2(4) .
C2 C1 C6 C5 7(4) .
C7 C1 C6 C5 -178(3) .
C4 C5 C6 C1 -1(4) .
C4 C5 C6 O1A -177(2) .
C4A C5A C6A C1A 0(2) .
C2A C1A C6A C5A -1.5(19) .
C7 C1A C6A C5A -174.9(13) .
Cu1 O3 C7 O2 2.2(4) .
Cu1 O3 C7 C1 179.0(16) .
Cu1 O3 C7 C1A -178.4(6) .
C6 C1 C7 O2 178.5(19) .
C2 C1 C7 O2 -7(3) .
C6 C1 C7 O3 1(3) .
C2 C1 C7 O3 176(2) .
C6A C1A C7 O2 177.0(9) .
C2A C1A C7 O2 3.5(14) .
C6A C1A C7 O3 -2.4(13) .
C2A C1A C7 O3 -176.0(8) .
C12 N1 C8 C9 169.2(2) .
C10 N1 C8 C9 -68.2(2) .
Cu1 N1 C8 C9 49.6(2) .
N1 C8 C9 O4 -53.3(3) .
C8 N1 C10 C11 138.9(2) .
C12 N1 C10 C11 -100.1(2) .
Cu1 N1 C10 C11 20.0(2) .
Cu1 O5 C11 C10 164.76(14) 3_666
Cu1 O5 C11 C10 48.5(2) .
N1 C10 C11 O5 -45.2(3) .
C8 N1 C12 C13 -174.59(19) .
C10 N1 C12 C13 62.8(2) .
Cu1 N1 C12 C13 -55.5(2) .
N1 C12 C13 O6 55.0(3) .
