#------------------------------------------------------------------------------
#$Date: 2021-05-11 11:03:02 +0300 (Tue, 11 May 2021) $
#$Revision: 265093 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/24/1562482.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_1562482
loop_
_publ_author_name
'Zavakhina, Marina S.'
'Samsonenko, Denis G.'
'Virovets, Alexander V.'
'Dybtsev, Danil N.'
'Fedin, Vladimir P.'
_publ_section_title
;
 Homochiral Cu(II) and Ni(II) malates with tunable structural features
;
_journal_issue                   1
_journal_name_full               'Journal of Solid State Chemistry'
_journal_page_first              125
_journal_page_last               129
_journal_paper_doi               10.1016/j.jssc.2013.11.011
_journal_volume                  210
_journal_year                    2014
_chemical_formula_structural     '(Cu (C4 H4 O5) (C10 H8 N2)) . (H2 O)'
_chemical_formula_sum            'C14 H14 Cu N2 O6'
_chemical_formula_weight         369.81
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.6027(2)
_cell_length_b                   8.6027(2)
_cell_length_c                   43.7712(10)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.41
_cell_volume                     3239.35(13)
_computing_cell_refinement       'SAINT (Bruker-AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker-AXS, 2004)'
_computing_data_reduction        'SAINT (Bruker-AXS, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker-AXS, 2004)'
_computing_publication_material  'CIFTAB-97 (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1998)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 25
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Nonius X8Apex CCD'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_number            20882
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.41
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.379
_exptl_absorpt_correction_T_max  0.8744
_exptl_absorpt_correction_T_min  0.7243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS, 2004)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.832
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.159
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.217
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0826P)²+6.5365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1508
_reflns_number_gt                3943
_reflns_number_total             4049
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            JSSC-2014-210-125.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Tetragonal' was changed to
'tetragonal' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8369 2020-08-20 11:38:08Z andrius 
;
_cod_database_code               1562482
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.51466(5) 0.84955(5) 0.142439(9) 0.00967(14) Uani 1 1 d . . .
O1 O 0.5279(3) 0.6229(3) 0.14253(6) 0.0146(5) Uani 1 1 d . . .
O2 O 0.7603(3) 0.6244(3) 0.11993(7) 0.0178(6) Uani 1 1 d . . .
C1 C 0.6440(5) 0.5576(4) 0.12996(8) 0.0118(7) Uani 1 1 d . . .
C2 C 0.6306(5) 0.3798(4) 0.12789(9) 0.0161(8) Uani 1 1 d . . .
H2 H 0.5201 0.3554 0.1227 0.019 Uiso 1 1 calc R . .
O3 O 0.7249(4) 0.3155(4) 0.10431(7) 0.0228(7) Uani 1 1 d . . .
H3 H 0.8129 0.3578 0.1046 0.034 Uiso 1 1 calc R . .
C3 C 0.6636(6) 0.3069(4) 0.15885(9) 0.0194(8) Uani 1 1 d . . .
H3A H 0.7690 0.3371 0.1657 0.023 Uiso 1 1 calc R . .
H3B H 0.5878 0.3461 0.1740 0.023 Uiso 1 1 calc R . .
C4 C 0.6528(5) 0.1311(4) 0.15699(8) 0.0150(7) Uani 1 1 d . . .
O4 O 0.5262(3) 0.0778(3) 0.14554(6) 0.0136(5) Uani 1 1 d . . .
O5 O 0.7616(4) 0.0464(4) 0.16514(8) 0.0260(7) Uani 1 1 d . . .
N1 N 0.4684(4) 0.8425(4) 0.18771(7) 0.0143(6) Uani 1 1 d . . .
C101 C 0.3506(5) 0.9255(5) 0.19896(9) 0.0209(8) Uani 1 1 d . . .
H101 H 0.2827 0.9760 0.1850 0.025 Uiso 1 1 calc R . .
C102 C 0.3224(5) 0.9419(5) 0.22989(9) 0.0226(9) Uani 1 1 d . . .
H102 H 0.2360 1.0010 0.2368 0.027 Uiso 1 1 calc R . .
C103 C 0.4224(5) 0.8705(5) 0.25106(9) 0.0172(8) Uani 1 1 d . . .
C104 C 0.5419(6) 0.7801(7) 0.23900(9) 0.0369(14) Uani 1 1 d . . .
H104 H 0.6110 0.7263 0.2522 0.044 Uiso 1 1 calc R . .
C105 C 0.5597(6) 0.7689(7) 0.20752(9) 0.0325(12) Uani 1 1 d . . .
H105 H 0.6411 0.7056 0.1998 0.039 Uiso 1 1 calc R . .
C106 C 0.4555(5) 0.8257(5) 0.33669(8) 0.0165(7) Uani 1 1 d . . .
H106 H 0.5086 0.7611 0.3509 0.020 Uiso 1 1 calc R . .
C107 C 0.4758(5) 0.7986(5) 0.30561(8) 0.0186(7) Uani 1 1 d . . .
H107 H 0.5419 0.7171 0.2989 0.022 Uiso 1 1 calc R . .
C108 C 0.3987(5) 0.8919(5) 0.28445(9) 0.0158(8) Uani 1 1 d . . .
C109 C 0.3002(5) 1.0060(5) 0.29600(9) 0.0225(9) Uani 1 1 d . . .
H109 H 0.2427 1.0701 0.2824 0.027 Uiso 1 1 calc R . .
C110 C 0.2858(5) 1.0261(5) 0.32730(9) 0.0200(8) Uani 1 1 d . . .
H110 H 0.2179 1.1044 0.3348 0.024 Uiso 1 1 calc R . .
N2 N 0.3647(4) 0.9386(4) 0.34731(7) 0.0125(6) Uani 1 1 d . . .
O1W O 1.0141(6) 0.1511(8) 0.19721(11) 0.0651(16) Uani 1 1 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'
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'
Cu Cu 0.3201 1.2651 '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
O1 Cu1 O2 98.95(11) . 6_465
O1 Cu1 O4 172.55(12) . 1_565
O1 Cu1 N1 88.82(12) . .
O1 Cu1 N2 93.15(12) . 3_654
O4 Cu1 O2 88.09(11) 1_565 6_465
O4 Cu1 N1 88.42(12) 1_565 .
O4 Cu1 N2 89.60(12) 1_565 3_654
N1 Cu1 O2 92.70(12) . 6_465
N2 Cu1 O2 87.25(12) 3_654 6_465
N2 Cu1 N1 178.02(13) 3_654 .
C1 O1 Cu1 119.1(2) . .
C1 O2 Cu1 156.1(3) . 6_565
O1 C1 C2 114.0(3) . .
O2 C1 O1 125.8(3) . .
O2 C1 C2 120.2(3) . .
C1 C2 H2 107.1 . .
O3 C2 C1 112.7(3) . .
O3 C2 H2 107.1 . .
O3 C2 C3 112.3(3) . .
C3 C2 C1 110.1(3) . .
C3 C2 H2 107.1 . .
C2 O3 H3 109.5 . .
C2 C3 H3A 109.5 . .
C2 C3 H3B 109.5 . .
H3A C3 H3B 108.1 . .
C4 C3 C2 110.6(3) . .
C4 C3 H3A 109.5 . .
C4 C3 H3B 109.5 . .
O4 C4 C3 115.4(4) . .
O5 C4 C3 121.6(4) . .
O5 C4 O4 122.9(4) . .
C4 O4 Cu1 115.2(2) . 1_545
C101 N1 Cu1 119.7(3) . .
C105 N1 Cu1 122.5(3) . .
C105 N1 C101 117.6(3) . .
N1 C101 H101 118.3 . .
N1 C101 C102 123.3(4) . .
C102 C101 H101 118.3 . .
C101 C102 H102 120.2 . .
C101 C102 C103 119.6(4) . .
C103 C102 H102 120.2 . .
C102 C103 C108 120.7(4) . .
C104 C103 C102 116.5(4) . .
C104 C103 C108 122.8(4) . .
C103 C104 H104 120.1 . .
C105 C104 C103 119.7(4) . .
C105 C104 H104 120.1 . .
N1 C105 C104 123.3(4) . .
N1 C105 H105 118.4 . .
C104 C105 H105 118.4 . .
C107 C106 H106 118.7 . .
N2 C106 H106 118.7 . .
N2 C106 C107 122.5(4) . .
C106 C107 H107 120.2 . .
C106 C107 C108 119.6(4) . .
C108 C107 H107 120.2 . .
C107 C108 C103 121.2(4) . .
C109 C108 C103 121.8(4) . .
C109 C108 C107 117.0(4) . .
C108 C109 H109 120.0 . .
C110 C109 C108 120.1(4) . .
C110 C109 H109 120.0 . .
C109 C110 H110 119.0 . .
N2 C110 C109 122.1(4) . .
N2 C110 H110 119.0 . .
C106 N2 Cu1 121.7(3) . 4_465
C106 N2 C110 118.6(3) . .
C110 N2 Cu1 119.7(3) . 4_465
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.953(3) .
Cu1 O2 2.265(3) 6_465
Cu1 O4 1.970(3) 1_565
Cu1 N1 2.022(3) .
Cu1 N2 2.020(3) 3_654
O1 C1 1.272(5) .
O2 Cu1 2.265(3) 6_565
O2 C1 1.235(5) .
C1 C2 1.536(5) .
C2 H2 1.0000 .
C2 O3 1.425(5) .
C2 C3 1.520(5) .
O3 H3 0.8400 .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C3 C4 1.518(5) .
C4 O4 1.283(5) .
C4 O5 1.239(5) .
O4 Cu1 1.970(3) 1_545
N1 C101 1.334(5) .
N1 C105 1.330(5) .
C101 H101 0.9500 .
C101 C102 1.383(5) .
C102 H102 0.9500 .
C102 C103 1.405(6) .
C103 C104 1.393(6) .
C103 C108 1.487(5) .
C104 H104 0.9500 .
C104 C105 1.390(6) .
C105 H105 0.9500 .
C106 H106 0.9500 .
C106 C107 1.391(5) .
C106 N2 1.330(5) .
C107 H107 0.9500 .
C107 C108 1.393(6) .
C108 C109 1.392(6) .
C109 H109 0.9500 .
C109 C110 1.386(5) .
C110 H110 0.9500 .
C110 N2 1.339(5) .
N2 Cu1 2.020(3) 4_465
