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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/26/4502689.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_4502689
loop_
_publ_author_name
'Keene, Tony D.'
'Zimmermann, Iwan'
'Neels, Antonia'
'Sereda, Olha'
'Hauser, Jürg'
'Liu, Shi-Xia'
'Decurtins, Silvio'
_publ_section_title
;
 Crystal Engineering of a Series of Arylammonium Copper(II) Malonates
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1854
_journal_paper_doi               10.1021/cg9015349
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C6 H8 Cu O10, 2(C8 H10 N O2)'
_chemical_formula_sum            'C22 H28 Cu N2 O14'
_chemical_formula_weight         608.00
_chemical_melting_point          ?
_chemical_name_common
;
 [4-cbnlH]2[Cu(II)(mal)2(H2O)2]
;
_chemical_name_systematic
;
 [4-cbnlH]2[Cu(II)(mal)2(H2O)2]
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 102.544(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.8639(6)
_cell_length_b                   8.2453(4)
_cell_length_c                   11.7648(5)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      37.302
_cell_measurement_theta_min      2.793
_cell_volume                     1312.76(10)
_computing_cell_refinement       'SAINT-Plus Version 7.24A (Bruker, 2009)'
_computing_data_collection       'APEX2 Version 2.1-4 (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus Version 7.24A (Bruker, 2009)'
_computing_molecular_graphics    'DIAMOND 2.1a (Brandenberg, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type
'Bruker SMART APEX II CCD area-detector diffractometer'
_diffrn_measurement_method       'rotation method'
_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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            65362
_diffrn_reflns_theta_full        35.70
_diffrn_reflns_theta_max         37.81
_diffrn_reflns_theta_min         2.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.906
_exptl_absorpt_correction_T_max  0.8147
_exptl_absorpt_correction_T_min  0.7145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008-1 (Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             630
_exptl_crystal_size_max          0.479
_exptl_crystal_size_mid          0.439
_exptl_crystal_size_min          0.224
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         6432
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0285
_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)+(0.0478P)²+0.2693P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0866
_reflns_number_gt                5517
_reflns_number_total             6432
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg9015349_si_005.cif
_cod_data_source_block           cbnl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'n/a' was changed to '?' - the value
is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4502689
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.0000 0.0000 0.5000 0.01527(4) Uani 1 2 d S
O4 O 0.06917(5) -0.11790(7) 0.39894(5) 0.01747(11) Uani 1 1 d .
O1 O 0.05151(5) 0.20733(7) 0.46069(5) 0.01869(11) Uani 1 1 d .
O3 O 0.13414(5) -0.15179(8) 0.24543(6) 0.02107(12) Uani 1 1 d .
N1 N 0.15489(5) 0.61179(8) 0.51793(6) 0.01706(12) Uani 1 1 d .
H1A H 0.1259 0.6862 0.4641 0.026 Uiso 1 1 calc R
H1B H 0.1324 0.6254 0.5845 0.026 Uiso 1 1 calc R
H1C H 0.1396 0.5101 0.4895 0.026 Uiso 1 1 calc R
O1W O -0.15021(6) 0.03703(9) 0.34276(6) 0.02398(13) Uani 1 1 d D
O2 O 0.12448(5) 0.36851(7) 0.35537(6) 0.02247(12) Uani 1 1 d .
C3 C 0.08504(6) 0.23618(9) 0.37076(6) 0.01530(12) Uani 1 1 d .
C1 C 0.09541(6) -0.06401(9) 0.30874(6) 0.01421(12) Uani 1 1 d .
C2 C 0.07582(7) 0.11184(9) 0.27397(7) 0.01897(14) Uani 1 1 d .
H2A H 0.0081 0.1193 0.2253 0.023 Uiso 1 1 calc R
H2B H 0.1220 0.1431 0.2243 0.023 Uiso 1 1 calc R
C5 C 0.39973(7) 0.28376(12) 0.79919(8) 0.02378(16) Uani 1 1 d .
C10 C 0.26413(7) 0.63414(11) 0.54353(8) 0.02324(16) Uani 1 1 d .
H10A H 0.2808 0.7451 0.5736 0.028 Uiso 1 1 calc R
H10B H 0.2885 0.6212 0.4710 0.028 Uiso 1 1 calc R
C8 C 0.31393(7) 0.51146(10) 0.63248(8) 0.02169(15) Uani 1 1 d .
C7 C 0.36866(8) 0.56205(12) 0.73983(9) 0.02801(18) Uani 1 1 d .
H7 H 0.3763 0.6746 0.7567 0.034 Uiso 1 1 calc R
C4 C 0.44319(7) 0.16025(13) 0.88757(8) 0.02494(17) Uani 1 1 d .
C9 C 0.30317(8) 0.34610(12) 0.60842(9) 0.02719(18) Uani 1 1 d .
H9 H 0.2670 0.3109 0.5345 0.033 Uiso 1 1 calc R
O6 O 0.50336(6) 0.21366(12) 0.97984(7) 0.03302(17) Uani 1 1 d .
H6O H 0.5240 0.1356 1.0244 0.050 Uiso 1 1 calc R
O5 O 0.42134(7) 0.01416(10) 0.87050(8) 0.03287(18) Uani 1 1 d .
C6 C 0.34502(7) 0.23238(12) 0.69180(9) 0.02746(18) Uani 1 1 d .
H6 H 0.3363 0.1198 0.6755 0.033 Uiso 1 1 calc R
C11 C 0.41240(8) 0.44872(14) 0.82297(9) 0.02945(19) Uani 1 1 d .
H11 H 0.4508 0.4839 0.8957 0.035 Uiso 1 1 calc R
H1W H -0.1507(12) 0.1291(8) 0.3048(10) 0.035 Uiso 1 1 d D
H2W H -0.1452(12) -0.0393(11) 0.2921(9) 0.035 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'
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
O4 Cu1 O4 180.00(2) 3_556 .
O4 Cu1 O1 87.78(2) 3_556 .
O4 Cu1 O1 92.22(2) . .
O4 Cu1 O1 92.22(2) 3_556 3_556
O4 Cu1 O1 87.78(2) . 3_556
O1 Cu1 O1 180.0 . 3_556
O4 Cu1 O1W 87.07(3) 3_556 .
O4 Cu1 O1W 92.93(3) . .
O1 Cu1 O1W 90.38(3) . .
O1 Cu1 O1W 89.62(3) 3_556 .
O4 Cu1 O1W 92.93(3) 3_556 3_556
O4 Cu1 O1W 87.07(3) . 3_556
O1 Cu1 O1W 89.62(3) . 3_556
O1 Cu1 O1W 90.38(3) 3_556 3_556
O1W Cu1 O1W 180.0 . 3_556
C1 O4 Cu1 127.11(5) . .
C3 O1 Cu1 125.68(5) . .
C10 N1 H1A 109.5 . .
C10 N1 H1B 109.5 . .
H1A N1 H1B 109.5 . .
C10 N1 H1C 109.5 . .
H1A N1 H1C 109.5 . .
H1B N1 H1C 109.5 . .
Cu1 O1W H1W 113.3(10) . .
Cu1 O1W H2W 103.9(10) . .
H1W O1W H2W 105.44(16) . .
O2 C3 O1 122.40(7) . .
O2 C3 C2 116.68(7) . .
O1 C3 C2 120.89(7) . .
O3 C1 O4 122.37(7) . .
O3 C1 C2 118.14(7) . .
O4 C1 C2 119.45(6) . .
C1 C2 C3 117.60(6) . .
C1 C2 H2A 107.9 . .
C3 C2 H2A 107.9 . .
C1 C2 H2B 107.9 . .
C3 C2 H2B 107.9 . .
H2A C2 H2B 107.2 . .
C6 C5 C11 120.01(8) . .
C6 C5 C4 119.01(9) . .
C11 C5 C4 120.97(9) . .
N1 C10 C8 110.41(7) . .
N1 C10 H10A 109.6 . .
C8 C10 H10A 109.6 . .
N1 C10 H10B 109.6 . .
C8 C10 H10B 109.6 . .
H10A C10 H10B 108.1 . .
C7 C8 C9 119.45(8) . .
C7 C8 C10 120.41(8) . .
C9 C8 C10 120.12(8) . .
C8 C7 C11 120.38(9) . .
C8 C7 H7 119.8 . .
C11 C7 H7 119.8 . .
O5 C4 O6 123.59(9) . .
O5 C4 C5 120.10(9) . .
O6 C4 C5 116.31(9) . .
C6 C9 C8 120.45(9) . .
C6 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
C4 O6 H6O 109.5 . .
C9 C6 C5 119.83(9) . .
C9 C6 H6 120.1 . .
C5 C6 H6 120.1 . .
C5 C11 C7 119.85(9) . .
C5 C11 H11 120.1 . .
C7 C11 H11 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O4 1.9426(6) 3_556
Cu1 O4 1.9426(6) .
Cu1 O1 1.9467(6) .
Cu1 O1 1.9467(6) 3_556
Cu1 O1W 2.4857(7) .
Cu1 O1W 2.4857(7) 3_556
O4 C1 1.2742(9) .
O1 C3 1.2672(9) .
O3 C1 1.2413(9) .
N1 C10 1.4900(11) .
N1 H1A 0.9100 .
N1 H1B 0.9100 .
N1 H1C 0.9100 .
O1W H1W 0.8797(10) .
O1W H2W 0.8797(10) .
O2 C3 1.2511(9) .
C3 C2 1.5169(11) .
C1 C2 1.5150(10) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C5 C6 1.3910(13) .
C5 C11 1.3920(16) .
C5 C4 1.4863(12) .
C10 C8 1.5103(12) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C8 C7 1.3887(14) .
C8 C9 1.3939(13) .
C7 C11 1.3929(14) .
C7 H7 0.9500 .
C4 O5 1.2477(13) .
C4 O6 1.2941(12) .
C9 C6 1.3896(13) .
C9 H9 0.9500 .
O6 H6O 0.8400 .
C6 H6 0.9500 .
C11 H11 0.9500 .
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
O1 Cu1 O4 C1 -26.47(7) .
O1 Cu1 O4 C1 153.53(7) 3_556
O1W Cu1 O4 C1 64.02(7) .
O1W Cu1 O4 C1 -115.98(7) 3_556
O4 Cu1 O1 C3 -159.26(7) 3_556
O4 Cu1 O1 C3 20.74(7) .
O1W Cu1 O1 C3 -72.20(7) .
O1W Cu1 O1 C3 107.80(7) 3_556
Cu1 O1 C3 O2 -174.02(6) .
Cu1 O1 C3 C2 8.06(11) .
Cu1 O4 C1 O3 -175.49(6) .
Cu1 O4 C1 C2 2.27(11) .
O3 C1 C2 C3 -146.17(8) .
O4 C1 C2 C3 35.97(11) .
O2 C3 C2 C1 140.09(8) .
O1 C3 C2 C1 -41.88(11) .
N1 C10 C8 C7 -117.64(10) .
N1 C10 C8 C9 60.74(12) .
C9 C8 C7 C11 -0.08(16) .
C10 C8 C7 C11 178.31(10) .
C6 C5 C4 O5 -8.17(15) .
C11 C5 C4 O5 171.28(10) .
C6 C5 C4 O6 171.62(9) .
C11 C5 C4 O6 -8.93(14) .
C7 C8 C9 C6 1.33(16) .
C10 C8 C9 C6 -177.07(9) .
C8 C9 C6 C5 -1.31(16) .
C11 C5 C6 C9 0.04(16) .
C4 C5 C6 C9 179.49(9) .
C6 C5 C11 C7 1.19(16) .
C4 C5 C11 C7 -178.25(9) .
C8 C7 C11 C5 -1.17(17) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145000
