#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/26/4502690.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_4502690
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 H9 F3 N)'
_chemical_formula_sum            'C22 H26 Cu F6 N2 O10'
_chemical_formula_weight         655.99
_chemical_melting_point          ?
_chemical_name_common
;
 [4-fmbnlH]2[Cu(mal)2(H2O)2]
;
_chemical_name_systematic
;
 [4-fmbnlH]2[Cu(mal)2(H2O)2]
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000
_cell_angle_beta                 100.635(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            2
_cell_length_a                   11.887(5)
_cell_length_b                   8.328(5)
_cell_length_c                   13.892(5)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      52.1
_cell_measurement_theta_min      3.3
_cell_volume                     1351.6(11)
_computing_cell_refinement       'X-Area V1.35'
_computing_data_collection       'X-Area V1.35 (Stoe & Cie, 2006)'
_computing_data_reduction        'X-RED32 V1.31 (Stoe & Cie, 2006)'
_computing_molecular_graphics    'DIAMOND 2.1a  (Brandenberg, 1999)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'STOE IPDS-2'
_diffrn_measurement_method       'phi + omega 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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10253
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.906
_exptl_absorpt_correction_T_max  0.8467
_exptl_absorpt_correction_T_min  0.6453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             670
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2636
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0309
_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)+(0.0506P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0778
_reflns_number_gt                2105
_reflns_number_total             2636
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg9015349_si_006.cif
_cod_data_source_block           fmbnl
_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/a'
_cod_database_code               4502690
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.5000 0.0000 0.5000 0.01588(11) Uani 1 2 d S
O1W O 0.59150(12) 0.03791(17) 0.35188(12) 0.0263(3) Uani 1 1 d D
O3 O 0.36770(11) 0.11592(16) 0.43134(10) 0.0182(3) Uani 1 1 d .
O2 O 0.30031(11) -0.36789(16) 0.38059(10) 0.0218(3) Uani 1 1 d .
F1 F 0.58595(18) 0.8803(2) -0.03693(12) 0.0692(5) Uani 1 1 d .
O1 O 0.43740(11) -0.20469(16) 0.44973(10) 0.0184(3) Uani 1 1 d .
N11 N 0.44829(13) 0.3903(2) 0.35369(11) 0.0178(3) Uani 1 1 d .
H11A H 0.4102 0.3150 0.3828 0.027 Uiso 1 1 calc R
H11B H 0.4247 0.4900 0.3680 0.027 Uiso 1 1 calc R
H11C H 0.5249 0.3806 0.3763 0.027 Uiso 1 1 calc R
O4 O 0.18431(11) 0.15107(16) 0.37226(10) 0.0200(3) Uani 1 1 d .
F2 F 0.68423(19) 0.9648(2) 0.09464(14) 0.0753(6) Uani 1 1 d .
F3 F 0.74687(19) 0.7747(3) 0.01633(19) 0.0952(8) Uani 1 1 d .
C1 C 0.33305(16) -0.2350(2) 0.41668(13) 0.0152(4) Uani 1 1 d .
C2 C 0.24108(16) -0.1116(2) 0.42242(15) 0.0197(4) Uani 1 1 d .
H2A H 0.1728 -0.1418 0.3735 0.024 Uiso 1 1 calc R
H2B H 0.2198 -0.1215 0.4878 0.024 Uiso 1 1 calc R
C14 C 0.4632(2) 0.6502(3) 0.20178(18) 0.0401(6) Uani 1 1 d .
H14 H 0.4081 0.6847 0.2389 0.048 Uiso 1 1 calc R
C12 C 0.4240(2) 0.3661(3) 0.24629(15) 0.0280(5) Uani 1 1 d .
H12A H 0.3405 0.3745 0.2219 0.034 Uiso 1 1 calc R
H12B H 0.4487 0.2571 0.2309 0.034 Uiso 1 1 calc R
C18 C 0.5973(2) 0.7136(3) 0.10030(17) 0.0340(5) Uani 1 1 d .
C3 C 0.26554(16) 0.0634(2) 0.40674(13) 0.0147(4) Uani 1 1 d .
C13 C 0.48508(18) 0.4885(3) 0.19531(14) 0.0244(4) Uani 1 1 d .
C16 C 0.5192(3) 0.7626(3) 0.15569(19) 0.0416(6) Uani 1 1 d .
H16 H 0.5040 0.8737 0.1621 0.050 Uiso 1 1 calc R
C15 C 0.5659(2) 0.4417(3) 0.14192(19) 0.0422(6) Uani 1 1 d .
H15 H 0.5838 0.3310 0.1378 0.051 Uiso 1 1 calc R
C17 C 0.6212(3) 0.5535(4) 0.0943(2) 0.0503(7) Uani 1 1 d .
H17 H 0.6763 0.5194 0.0570 0.060 Uiso 1 1 calc R
C19 C 0.6529(3) 0.8330(4) 0.0448(2) 0.0495(7) Uani 1 1 d .
H1W H 0.645(2) -0.035(3) 0.352(3) 0.074 Uiso 1 1 d D
H2W H 0.627(2) 0.1301(19) 0.352(3) 0.074 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'
F F 0.0171 0.0103 '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 O1 180.00(9) . 3_656
O1 Cu1 O3 87.82(6) . 3_656
O1 Cu1 O3 92.18(6) 3_656 3_656
O1 Cu1 O3 92.18(6) . .
O1 Cu1 O3 87.82(6) 3_656 .
O3 Cu1 O3 180.00(7) 3_656 .
H1W O1W H2W 105.0(15) . .
C3 O3 Cu1 127.30(12) . .
C1 O1 Cu1 126.25(12) . .
C12 N11 H11A 109.5 . .
C12 N11 H11B 109.5 . .
H11A N11 H11B 109.5 . .
C12 N11 H11C 109.5 . .
H11A N11 H11C 109.5 . .
H11B N11 H11C 109.5 . .
O2 C1 O1 122.32(17) . .
O2 C1 C2 116.66(17) . .
O1 C1 C2 120.99(17) . .
C3 C2 C1 119.18(16) . .
C3 C2 H2A 107.5 . .
C1 C2 H2A 107.5 . .
C3 C2 H2B 107.5 . .
C1 C2 H2B 107.5 . .
H2A C2 H2B 107.0 . .
C16 C14 C13 121.4(2) . .
C16 C14 H14 119.3 . .
C13 C14 H14 119.3 . .
N11 C12 C13 111.19(17) . .
N11 C12 H12A 109.4 . .
C13 C12 H12A 109.4 . .
N11 C12 H12B 109.4 . .
C13 C12 H12B 109.4 . .
H12A C12 H12B 108.0 . .
C17 C18 C16 119.6(2) . .
C17 C18 C19 120.2(2) . .
C16 C18 C19 120.2(2) . .
O4 C3 O3 122.57(18) . .
O4 C3 C2 117.99(17) . .
O3 C3 C2 119.42(16) . .
C15 C13 C14 118.2(2) . .
C15 C13 C12 120.6(2) . .
C14 C13 C12 121.2(2) . .
C18 C16 C14 119.6(2) . .
C18 C16 H16 120.2 . .
C14 C16 H16 120.2 . .
C13 C15 C17 120.7(3) . .
C13 C15 H15 119.7 . .
C17 C15 H15 119.7 . .
C18 C17 C15 120.4(3) . .
C18 C17 H17 119.8 . .
C15 C17 H17 119.8 . .
F2 C19 F1 105.7(3) . .
F2 C19 F3 106.7(3) . .
F1 C19 F3 104.9(2) . .
F2 C19 C18 113.3(2) . .
F1 C19 C18 113.0(2) . .
F3 C19 C18 112.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9379(16) .
Cu1 O1 1.9379(16) 3_656
Cu1 O3 1.9394(14) 3_656
Cu1 O3 1.9394(14) .
O1W H1W 0.877(10) .
O1W H2W 0.878(10) .
O3 C3 1.277(2) .
O2 C1 1.247(2) .
F1 C19 1.321(3) .
O1 C1 1.266(2) .
N11 C12 1.480(3) .
N11 H11A 0.9100 .
N11 H11B 0.9100 .
N11 H11C 0.9100 .
O4 C3 1.235(2) .
F2 C19 1.314(4) .
F3 C19 1.343(4) .
C1 C2 1.513(3) .
C2 C3 1.510(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C14 C16 1.374(4) .
C14 C13 1.378(3) .
C14 H14 0.9500 .
C12 C13 1.503(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C18 C17 1.369(4) .
C18 C16 1.372(4) .
C18 C19 1.486(4) .
C13 C15 1.374(3) .
C16 H16 0.9500 .
C15 C17 1.378(4) .
C15 H15 0.9500 .
C17 H17 0.9500 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145001
