#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/57/2215705.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2215705
loop_
_publ_author_name
'Hökelek, Tuncer'
'Çaylak, Nagihan'
'Necefoğlu, Hacali'
_publ_section_title
Diaquabis(N,N-diethylnicotinamide-κN)bis(4-fluorobenzoato-κO)zinc(II)
_journal_coeditor_code           XU2321
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2561
_journal_page_last               m2562
_journal_paper_doi               10.1107/S1600536807045382
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Zn (C7 H4 F O2)2 (C10 H14 N2 O)2 (H2 O)2]'
_chemical_formula_moiety         'C34 H40 F2 N4 O8 Zn'
_chemical_formula_sum            'C34 H40 F2 N4 O8 Zn'
_chemical_formula_weight         736.10
_chemical_name_systematic
;
Diaquabis(N,N-diethylnicotinamide-\kN)bis(4-fluorobenzoato-\kO)zinc(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.44(2)
_cell_angle_beta                 95.73(2)
_cell_angle_gamma                112.94(3)
_cell_formula_units_Z            1
_cell_length_a                   7.4261(2)
_cell_length_b                   8.7188(3)
_cell_length_c                   15.0798(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18.7
_cell_measurement_theta_min      3.6
_cell_volume                     876.1(2)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius TurboCAD-4'
_diffrn_measurement_method       'Non-profiled ω'
_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  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3830
_diffrn_reflns_theta_full        26.29
_diffrn_reflns_theta_max         26.29
_diffrn_reflns_theta_min         2.59
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  0.8905
_exptl_absorpt_correction_T_min  0.7601
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod-shaped
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.770
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3547
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.302
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.089P)²+0.159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1401
_reflns_number_gt                2934
_reflns_number_total             3547
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2321.cif
_cod_data_source_block           I
_cod_database_code               2215705
_cod_database_fobs_code          2215705
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Zn Zn 0.0000 0.0000 0.0000 0.0333(2) Uani d S 1
F F -0.3354(5) 0.3270(5) 0.4677(2) 0.0928(11) Uani d . 1
O O1 -0.0243(4) 0.1622(3) 0.11031(16) 0.0395(6) Uani d . 1
O O2 0.2370(4) 0.2052(4) 0.2136(2) 0.0531(7) Uani d . 1
O O3 0.7298(4) 0.2781(4) -0.12884(19) 0.0521(7) Uani d . 1
O O4 0.2728(4) 0.0115(4) 0.06928(18) 0.0435(6) Uani d D 1
H H41 0.277(7) 0.080(5) 0.1259(18) 0.062(13) Uiso d D 1
H H42 0.274(9) -0.089(4) 0.083(3) 0.087(18) Uiso d D 1
N N1 0.1816(4) 0.2150(3) -0.05431(19) 0.0344(6) Uani d . 1
N N2 0.6281(5) 0.3228(4) -0.2636(2) 0.0480(8) Uani d . 1
C C1 0.0665(5) 0.1978(4) 0.1908(2) 0.0347(7) Uani d . 1
C C2 -0.0416(5) 0.2319(4) 0.2653(2) 0.0355(7) Uani d . 1
C C3 -0.2285(5) 0.2311(4) 0.2447(2) 0.0398(8) Uani d . 1
H H3 -0.2871 0.2087 0.1841 0.048 Uiso calc R 1
C C4 -0.3288(6) 0.2630(5) 0.3124(3) 0.0494(9) Uani d . 1
H H4 -0.4537 0.2628 0.2984 0.059 Uiso calc R 1
C C5 -0.2385(7) 0.2948(6) 0.4006(3) 0.0572(11) Uani d . 1
C C6 -0.0556(7) 0.2952(6) 0.4250(3) 0.0577(11) Uani d . 1
H H6 0.0004 0.3161 0.4859 0.069 Uiso calc R 1
C C7 0.0434(6) 0.2635(5) 0.3561(3) 0.0452(9) Uani d . 1
H H7 0.1680 0.2635 0.3709 0.054 Uiso calc R 1
C C8 0.1608(5) 0.3607(4) -0.0438(2) 0.0369(7) Uani d . 1
H H8 0.0637 0.3706 -0.0119 0.044 Uiso calc R 1
C C9 0.2759(6) 0.4980(5) -0.0779(3) 0.0416(8) Uani d . 1
H H9 0.2578 0.5984 -0.0686 0.050 Uiso calc R 1
C C10 0.4202(5) 0.4829(4) -0.1265(2) 0.0384(8) Uani d . 1
H H10 0.4991 0.5727 -0.1511 0.046 Uiso calc R 1
C C11 0.4439(5) 0.3320(4) -0.1375(2) 0.0332(7) Uani d . 1
C C12 0.3234(5) 0.2019(4) -0.0995(2) 0.0342(7) Uani d . 1
H H12 0.3414 0.1014 -0.1055 0.041 Uiso calc R 1
C C13 0.6110(5) 0.3076(4) -0.1774(2) 0.0365(7) Uani d . 1
C C14 0.4823(8) 0.3458(7) -0.3274(3) 0.0639(12) Uani d . 1
H H14A 0.5514 0.4202 -0.3663 0.077 Uiso calc R 1
H H14B 0.4119 0.4005 -0.2933 0.077 Uiso calc R 1
C C15 0.3370(10) 0.1828(10) -0.3848(6) 0.113(2) Uani d . 1
H H15A 0.4033 0.1361 -0.4251 0.169 Uiso calc R 1
H H15B 0.2355 0.2022 -0.4198 0.169 Uiso calc R 1
H H15C 0.2779 0.1045 -0.3467 0.169 Uiso calc R 1
C C16 0.8024(7) 0.3107(6) -0.2978(3) 0.0619(12) Uani d . 1
H H16A 0.9172 0.3679 -0.2497 0.074 Uiso calc R 1
H H16B 0.8279 0.3705 -0.3477 0.074 Uiso calc R 1
C C17 0.7806(9) 0.1333(7) -0.3299(5) 0.0887(19) Uani d . 1
H H17A 0.7677 0.0760 -0.2797 0.133 Uiso calc R 1
H H17B 0.8957 0.1359 -0.3547 0.133 Uiso calc R 1
H H17C 0.6645 0.0739 -0.3761 0.133 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2840 1.4300 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Zn O1 . 2 180.00(14) ?
O1 Zn O4 . . 91.98(10) yes
O1 Zn O4 2 . 88.02(10) ?
O1 Zn O4 . 2 88.02(10) ?
O1 Zn O4 2 2 91.98(10) ?
O4 Zn O4 . 2 180.00(15) ?
O1 Zn N1 . 2 88.83(10) ?
O1 Zn N1 2 2 91.17(10) ?
O4 Zn N1 . 2 93.46(10) ?
O4 Zn N1 2 2 86.54(10) ?
O1 Zn N1 . . 91.17(10) yes
O1 Zn N1 2 . 88.83(10) ?
O4 Zn N1 . . 86.54(10) yes
O4 Zn N1 2 . 93.46(10) ?
N1 Zn N1 2 . 180.00(15) ?
C1 O1 Zn . . 126.6(2) ?
Zn O4 H41 . . 97(3) ?
Zn O4 H42 . . 118(4) ?
H41 O4 H42 . . 106(3) ?
C8 N1 C12 . . 118.1(3) ?
C8 N1 Zn . . 122.9(2) ?
C12 N1 Zn . . 118.9(2) ?
C13 N2 C14 . . 124.5(3) ?
C13 N2 C16 . . 117.9(3) ?
C14 N2 C16 . . 117.6(3) ?
O2 C1 O1 . . 125.5(3) ?
O2 C1 C2 . . 117.8(3) ?
O1 C1 C2 . . 116.7(3) ?
C3 C2 C7 . . 118.8(3) ?
C3 C2 C1 . . 120.7(3) ?
C7 C2 C1 . . 120.5(3) ?
C4 C3 C2 . . 121.3(3) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C5 C4 C3 . . 117.8(4) ?
C5 C4 H4 . . 121.1 ?
C3 C4 H4 . . 121.1 ?
F C5 C4 . . 118.3(4) ?
F C5 C6 . . 118.2(4) ?
C4 C5 C6 . . 123.6(4) ?
C5 C6 C7 . . 117.9(4) ?
C5 C6 H6 . . 121.1 ?
C7 C6 H6 . . 121.1 ?
C6 C7 C2 . . 120.7(4) ?
C6 C7 H7 . . 119.6 ?
C2 C7 H7 . . 119.6 ?
N1 C8 C9 . . 123.3(3) ?
N1 C8 H8 . . 118.4 ?
C9 C8 H8 . . 118.4 ?
C8 C9 C10 . . 118.5(3) ?
C8 C9 H9 . . 120.7 ?
C10 C9 H9 . . 120.7 ?
C11 C10 C9 . . 118.8(3) ?
C11 C10 H10 . . 120.6 ?
C9 C10 H10 . . 120.6 ?
C10 C11 C12 . . 118.6(3) ?
C10 C11 C13 . . 123.8(3) ?
C12 C11 C13 . . 117.0(3) ?
N1 C12 C11 . . 122.7(3) ?
N1 C12 H12 . . 118.6 ?
C11 C12 H12 . . 118.6 ?
O3 C13 N2 . . 122.0(3) ?
O3 C13 C11 . . 118.3(3) ?
N2 C13 C11 . . 119.7(3) ?
N2 C14 C15 . . 112.4(5) ?
N2 C14 H14A . . 109.1 ?
C15 C14 H14A . . 109.1 ?
N2 C14 H14B . . 109.1 ?
C15 C14 H14B . . 109.1 ?
H14A C14 H14B . . 107.8 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N2 C16 C17 . . 114.4(4) ?
N2 C16 H16A . . 108.7 ?
C17 C16 H16A . . 108.7 ?
N2 C16 H16B . . 108.7 ?
C17 C16 H16B . . 108.7 ?
H16A C16 H16B . . 107.6 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zn O1 . 2.090(2) yes
Zn O1 2 2.090(2) ?
Zn O4 . 2.143(2) yes
Zn O4 2 2.143(2) ?
Zn N1 2 2.169(3) ?
Zn N1 . 2.169(3) yes
F C5 . 1.357(5) ?
O1 C1 . 1.260(4) ?
O2 C1 . 1.252(4) ?
O3 C13 . 1.218(4) ?
O4 H41 . 0.960(16) ?
O4 H42 . 0.94(2) ?
N1 C8 . 1.327(4) ?
N1 C12 . 1.341(4) ?
N2 C13 . 1.340(5) ?
N2 C14 . 1.468(6) ?
N2 C16 . 1.476(5) ?
C2 C1 . 1.504(5) ?
C2 C3 . 1.388(5) ?
C3 H3 . 0.9300 ?
C2 C7 . 1.390(5) ?
C3 C4 . 1.380(5) ?
C4 H4 . 0.9300 ?
C4 C5 . 1.366(6) ?
C5 C6 . 1.370(7) ?
C6 H6 . 0.9300 ?
C7 C6 . 1.387(6) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C8 . 1.378(5) ?
C9 C10 . 1.393(5) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C10 . 1.383(5) ?
C11 C12 . 1.385(4) ?
C11 C13 . 1.504(5) ?
C12 H12 . 0.9300 ?
C14 C15 . 1.480(8) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 C17 . 1.490(7) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O4 H41 O2 . 0.96(3) 1.71(4) 2.654(4) 167(4) yes
O4 H42 O3 2_655 0.93(4) 1.87(4) 2.795(4) 171(4) yes
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_site_symmetry_1
_geom_torsion
O4 Zn O1 C1 . -17.4(3)
O4 Zn O1 C1 2 162.6(3)
N1 Zn O1 C1 2 76.0(3)
N1 Zn O1 C1 . -104.0(3)
O1 Zn N1 C8 . -31.8(3)
O1 Zn N1 C8 2 148.2(3)
O4 Zn N1 C8 . -123.7(3)
O4 Zn N1 C8 2 56.3(3)
O1 Zn N1 C12 . 147.2(3)
O1 Zn N1 C12 2 -32.8(3)
O4 Zn N1 C12 . 55.3(3)
O4 Zn N1 C12 2 -124.7(3)
Zn O1 C1 O2 . 31.6(5)
Zn O1 C1 C2 . -147.5(2)
C12 N1 C8 C9 . 0.7(5)
Zn N1 C8 C9 . 179.8(3)
C8 N1 C12 C11 . -1.9(5)
Zn N1 C12 C11 . 179.0(2)
C14 N2 C13 O3 . 175.3(4)
C16 N2 C13 O3 . -2.8(6)
C14 N2 C13 C11 . -6.4(6)
C16 N2 C13 C11 . 175.5(3)
C13 N2 C14 C15 . -94.3(5)
C16 N2 C14 C15 . 83.8(6)
C13 N2 C16 C17 . 82.9(6)
C14 N2 C16 C17 . -95.3(5)
C3 C2 C1 O2 . 177.9(3)
C7 C2 C1 O2 . -2.5(5)
C3 C2 C1 O1 . -2.8(5)
C7 C2 C1 O1 . 176.7(3)
C7 C2 C3 C4 . 0.7(5)
C1 C2 C3 C4 . -179.7(3)
C3 C2 C7 C6 . -0.5(6)
C1 C2 C7 C6 . 179.9(4)
C2 C3 C4 C5 . -0.2(6)
C3 C4 C5 F . 179.7(4)
C3 C4 C5 C6 . -0.6(7)
F C5 C6 C7 . -179.5(4)
C4 C5 C6 C7 . 0.8(7)
C2 C7 C6 C5 . -0.2(7)
C10 C9 C8 N1 . 0.6(6)
C8 C9 C10 C11 . -0.9(5)
C12 C11 C10 C9 . -0.1(5)
C13 C11 C10 C9 . -171.5(3)
C10 C11 C12 N1 . 1.6(5)
C13 C11 C12 N1 . 173.6(3)
C10 C11 C13 O3 . 115.7(4)
C12 C11 C13 O3 . -55.8(5)
C10 C11 C13 N2 . -62.7(5)
C12 C11 C13 N2 . 125.8(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168309323
