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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/4/50/26/4502693.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_4502693
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 H11 F N)'
_chemical_formula_sum            'C22 H30 Cu F2 N2 O10'
_chemical_formula_weight         584.02
_chemical_melting_point          ?
_chemical_name_common
;
 [4-fpeaH]2[Cu(mal)2(H2O)2]
;
_chemical_name_systematic
;
 [4-fpeaH]2[Cu(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                 113.501(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.839(3)
_cell_length_b                   8.4833(11)
_cell_length_c                   11.722(2)
_cell_measurement_reflns_used    6338
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.88
_cell_measurement_theta_min      1.61
_cell_volume                     1262.0(4)
_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_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE IPDS-2'
_diffrn_measurement_method       'phi + omega scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source
;
 sealed X-ray tube, 12 x 0.4 mm long-fine focus
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2059
_diffrn_reflns_av_sigmaI/netI    0.1356
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12616
_diffrn_reflns_theta_full        25.64
_diffrn_reflns_theta_max         25.64
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_T_max  0.7792
_exptl_absorpt_correction_T_min  0.6885
_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    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             606
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.801
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2385
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.800
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0544
_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)+(0.0573P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1316
_reflns_number_gt                1311
_reflns_number_total             2385
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg9015349_si_009.cif
_cod_data_source_block           fpea
_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               4502693
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 1.0000 0.0000 1.0000 0.0413(3) Uani 1 2 d S
O2 O 0.9269(2) -0.1113(3) 0.8450(2) 0.0422(8) Uani 1 1 d .
O1W O 0.8399(3) -0.0466(4) 1.0565(2) 0.0517(9) Uani 1 1 d D
O4 O 0.9460(2) 0.2037(3) 0.9266(2) 0.0414(7) Uani 1 1 d .
O3 O 0.8765(2) 0.3704(3) 0.7700(2) 0.0461(8) Uani 1 1 d .
O1 O 0.8510(2) -0.1369(3) 0.6406(2) 0.0452(8) Uani 1 1 d .
F1 F 0.6098(3) -0.0239(4) 0.6327(3) 0.0776(9) Uani 1 1 d .
N1 N 0.8382(3) 0.6143(4) 0.8979(3) 0.0453(9) Uani 1 1 d .
H1A H 0.8869 0.6744 0.8878 0.068 Uiso 1 1 calc R
H1B H 0.8421 0.5169 0.8718 0.068 Uiso 1 1 calc R
H1C H 0.8491 0.6120 0.9780 0.068 Uiso 1 1 calc R
C3 C 0.9115(3) 0.2385(5) 0.8110(4) 0.0388(10) Uani 1 1 d .
C1 C 0.8954(4) -0.0561(5) 0.7350(4) 0.0422(11) Uani 1 1 d .
C2 C 0.9164(4) 0.1164(5) 0.7175(3) 0.0424(11) Uani 1 1 d .
H2A H 0.8662 0.1482 0.6359 0.051 Uiso 1 1 calc R
H2B H 0.9859 0.1229 0.7162 0.051 Uiso 1 1 calc R
C11 C 0.6186(4) 0.1228(6) 0.6817(4) 0.0567(13) Uani 1 1 d .
C12 C 0.6675(4) 0.1412(6) 0.8087(4) 0.0598(14) Uani 1 1 d .
H12 H 0.6956 0.0552 0.8607 0.072 Uiso 1 1 calc R
C18 C 0.7324(4) 0.6802(5) 0.8247(4) 0.0501(12) Uani 1 1 d .
H18A H 0.7216 0.6845 0.7377 0.060 Uiso 1 1 calc R
H18B H 0.7293 0.7872 0.8522 0.060 Uiso 1 1 calc R
C15 C 0.5864(4) 0.3968(6) 0.6562(4) 0.0616(14) Uani 1 1 d .
H15 H 0.5609 0.4832 0.6040 0.074 Uiso 1 1 calc R
C14 C 0.6735(4) 0.2900(6) 0.8563(4) 0.0553(13) Uani 1 1 d .
H14 H 0.7066 0.3034 0.9420 0.066 Uiso 1 1 calc R
C16 C 0.6331(4) 0.4199(6) 0.7838(4) 0.0500(12) Uani 1 1 d .
C17 C 0.6442(4) 0.5847(6) 0.8367(4) 0.0569(13) Uani 1 1 d .
H17A H 0.6566 0.5776 0.9240 0.068 Uiso 1 1 calc R
H17B H 0.5783 0.6405 0.7945 0.068 Uiso 1 1 calc R
C13 C 0.5770(4) 0.2474(6) 0.6048(4) 0.0609(14) Uani 1 1 d .
H13 H 0.5428 0.2327 0.5193 0.073 Uiso 1 1 calc R
H1W H 0.842(4) 0.025(3) 1.112(3) 0.085(18) Uiso 1 1 d D
H2W H 0.834(5) -0.137(2) 1.090(4) 0.12(3) 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'
F F 0.0171 0.0103 '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
O2 Cu1 O2 180.000(1) . 3_757
O2 Cu1 O4 86.94(11) . 3_757
O2 Cu1 O4 93.06(11) 3_757 3_757
O2 Cu1 O4 93.06(11) . .
O2 Cu1 O4 86.94(11) 3_757 .
O4 Cu1 O4 180.000(1) 3_757 .
C1 O2 Cu1 127.6(3) . .
H1W O1W H2W 105.40(17) . .
C3 O4 Cu1 126.2(3) . .
C18 N1 H1A 109.5 . .
C18 N1 H1B 109.5 . .
H1A N1 H1B 109.5 . .
C18 N1 H1C 109.5 . .
H1A N1 H1C 109.5 . .
H1B N1 H1C 109.5 . .
O3 C3 O4 122.9(4) . .
O3 C3 C2 117.1(3) . .
O4 C3 C2 119.9(4) . .
O1 C1 O2 123.3(4) . .
O1 C1 C2 117.8(3) . .
O2 C1 C2 118.9(4) . .
C1 C2 C3 119.4(3) . .
C1 C2 H2A 107.5 . .
C3 C2 H2A 107.5 . .
C1 C2 H2B 107.5 . .
C3 C2 H2B 107.5 . .
H2A C2 H2B 107.0 . .
F1 C11 C13 119.3(4) . .
F1 C11 C12 119.0(5) . .
C13 C11 C12 121.7(5) . .
C14 C12 C11 118.0(5) . .
C14 C12 H12 121.0 . .
C11 C12 H12 121.0 . .
N1 C18 C17 113.0(4) . .
N1 C18 H18A 109.0 . .
C17 C18 H18A 109.0 . .
N1 C18 H18B 109.0 . .
C17 C18 H18B 109.0 . .
H18A C18 H18B 107.8 . .
C16 C15 C13 121.4(5) . .
C16 C15 H15 119.3 . .
C13 C15 H15 119.3 . .
C16 C14 C12 123.2(4) . .
C16 C14 H14 118.4 . .
C12 C14 H14 118.4 . .
C14 C16 C15 117.1(5) . .
C14 C16 C17 122.8(4) . .
C15 C16 C17 120.0(4) . .
C16 C17 C18 114.2(4) . .
C16 C17 H17A 108.7 . .
C18 C17 H17A 108.7 . .
C16 C17 H17B 108.7 . .
C18 C17 H17B 108.7 . .
H17A C17 H17B 107.6 . .
C11 C13 C15 118.7(4) . .
C11 C13 H13 120.6 . .
C15 C13 H13 120.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.936(3) .
Cu1 O2 1.936(3) 3_757
Cu1 O4 1.942(3) 3_757
Cu1 O4 1.942(3) .
O2 C1 1.275(4) .
O1W H1W 0.8800(11) .
O1W H2W 0.8800(11) .
O4 C3 1.279(4) .
O3 C3 1.238(5) .
O1 C1 1.237(5) .
F1 C11 1.356(6) .
N1 C18 1.480(5) .
N1 H1A 0.8900 .
N1 H1B 0.8900 .
N1 H1C 0.8900 .
C3 C2 1.529(5) .
C1 C2 1.521(6) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C11 C13 1.359(7) .
C11 C12 1.377(6) .
C12 C14 1.369(6) .
C12 H12 0.9300 .
C18 C17 1.517(6) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C15 C16 1.387(6) .
C15 C13 1.387(7) .
C15 H15 0.9300 .
C14 C16 1.367(6) .
C14 H14 0.9300 .
C16 C17 1.512(6) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C13 H13 0.9300 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145003
