(1,4,8,11-Tetra­aza­cyclo­tetra­deca­ne)palladium(II) diiodide monohydrate

Ha, K.

doi:10.1107/S2414314619010320

(1,4,8,11-Tetraazacyclotetradecane)palladium(II) diiodide monohydrate

In the title compound, [Pd(C₁₀H₂₄N₄)]I₂·H₂O, the Pd^II ion is four-coordinated in a slightly distorted square-planar coordination environment defined by four N atoms from a 1,4,8,11-tetraazacyclotetradecane ligand. The cationic complex, two I⁻ anions and the solvent water molecule are linked through intermolecular hydrogen bonds into a three-dimensional network structure.

Keywords: crystal structure; palladium(II) complex; 1,4,8,11-tetraazacyclotetradecane; iodide anion.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314619010320/wm4111sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314619010320/wm4111Isup2.hkl Contains datablock I

CCDC reference: 1941633

checkCIF report

Key indicators

Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.006 Å
R factor = 0.017
wR factor = 0.041
Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C6       --C7       .        7.7 s.u.

Alert level C
PLAT213_ALERT_2_C Atom C4              has ADP max/min Ratio .....        3.2 prolat
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         C6 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        Pd1 Check
PLAT245_ALERT_2_C U(iso) H2        Smaller than U(eq) N2        by      0.011 Ang   2
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note
PLAT354_ALERT_3_C Short  O-H (X0.82,N0.98A)  O1       - H1O      .       0.65 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1       --H1       .     Please Check

Alert level G
PLAT793_ALERT_4_G Model has Chirality at N1          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at N2          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at N3          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at N4          (Centro SPGR)          S Verify
PLAT794_ALERT_5_G Tentative Bond Valency for Pd1       (II)      .       2.15 Info
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015b).

(1,4,8,11-Tetraazacyclotetradecane)palladium(II) diiodide monohydrate top

Crystal data top

[Pd(C₁₀H₂₄N₄)]I₂·H₂O	F(000) = 1096
M_r = 578.55	D_x = 2.151 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.3993 (4) Å	Cell parameters from 9932 reflections
b = 13.7266 (5) Å	θ = 2.5–28.3°
c = 13.8797 (6) Å	µ = 4.49 mm⁻¹
β = 93.9017 (14)°	T = 223 K
V = 1786.61 (13) Å³	Block, yellow
Z = 4	0.23 × 0.18 × 0.11 mm

Data collection top

PHOTON 100 CMOS detector diffractometer	3307 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.043
φ and ω scans	θ_max = 26.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −11→11
T_min = 0.595, T_max = 0.745	k = −16→16
48072 measured reflections	l = −17→17
3544 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.017	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.041	w = 1/[σ²(F_o²) + (0.0147P)² + 1.4653P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.001
3544 reflections	Δρ_max = 0.49 e Å⁻³
188 parameters	Δρ_min = −0.72 e Å⁻³
0 restraints	Extinction correction: SHELXL2014/7 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00940 (16)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Hydrogen atoms on C atoms were positioned geometrically and allowed to ride on their respective parent atoms: C—H = 0.98 Å and U_iso(H) = 1.2U_eq(C). Hydrogen atoms bonded to N and O atoms were located from Fourier difference maps and refined isotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Pd1	0.25793 (2)	0.38024 (2)	0.72122 (2)	0.02194 (6)
I1	0.74413 (2)	0.36724 (2)	0.35324 (2)	0.04099 (7)
I2	0.19189 (2)	0.37008 (2)	0.21133 (2)	0.03941 (6)
N1	0.0680 (2)	0.42530 (15)	0.76680 (16)	0.0329 (4)
H1	0.068 (3)	0.482 (2)	0.7613 (18)	0.029 (7)*
N2	0.1427 (3)	0.34020 (17)	0.59789 (16)	0.0402 (5)
H2	0.123 (3)	0.286 (2)	0.6050 (18)	0.029 (7)*
N3	0.4495 (2)	0.33712 (17)	0.6762 (2)	0.0458 (6)
H3	0.456 (3)	0.279 (2)	0.687 (2)	0.042 (8)*
N4	0.3719 (3)	0.42382 (16)	0.84436 (18)	0.0449 (6)
H4	0.381 (3)	0.480 (2)	0.837 (2)	0.048 (9)*
C1	−0.0451 (3)	0.3835 (2)	0.6988 (3)	0.0572 (9)
H1A	−0.0622	0.3153	0.7154	0.069*
H1B	−0.1342	0.4197	0.7033	0.069*
C2	0.0026 (3)	0.3900 (2)	0.5994 (3)	0.0578 (9)
H2A	0.0117	0.4584	0.5806	0.069*
H2B	−0.0672	0.3586	0.5538	0.069*
C3	0.2129 (5)	0.3580 (2)	0.5075 (2)	0.0687 (11)
H3A	0.2255	0.4283	0.4990	0.082*
H3B	0.1516	0.3339	0.4527	0.082*
C4	0.3572 (5)	0.3081 (3)	0.5081 (3)	0.0863 (15)
H4A	0.3460	0.2400	0.5274	0.104*
H4B	0.3886	0.3083	0.4422	0.104*
C5	0.4711 (5)	0.3539 (3)	0.5739 (3)	0.0800 (14)
H5A	0.5640	0.3274	0.5592	0.096*
H5B	0.4727	0.4242	0.5617	0.096*
C6	0.5594 (3)	0.3852 (2)	0.7434 (4)	0.0789 (14)
H6A	0.6518	0.3529	0.7393	0.095*
H6B	0.5699	0.4537	0.7254	0.095*
C7	0.5134 (4)	0.3782 (2)	0.8436 (3)	0.0702 (12)
H7A	0.5085	0.3098	0.8634	0.084*
H7B	0.5815	0.4121	0.8885	0.084*
C8	0.3033 (4)	0.4087 (2)	0.9361 (2)	0.0646 (10)
H8A	0.3638	0.4370	0.9892	0.078*
H8B	0.2955	0.3386	0.9481	0.078*
C9	0.1575 (5)	0.4538 (2)	0.9350 (2)	0.0707 (11)
H9A	0.1256	0.4521	1.0008	0.085*
H9B	0.1648	0.5224	0.9163	0.085*
C10	0.0464 (4)	0.4057 (2)	0.8686 (2)	0.0572 (9)
H10A	0.0492	0.3352	0.8797	0.069*
H10B	−0.0481	0.4292	0.8834	0.069*
O1	0.5464 (3)	0.36267 (15)	0.13842 (18)	0.0472 (5)
H1O	0.478 (5)	0.365 (3)	0.144 (3)	0.061 (15)*
H2O	0.587 (5)	0.356 (3)	0.189 (3)	0.077 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.02275 (9)	0.02002 (9)	0.02342 (9)	−0.00007 (6)	0.00437 (6)	0.00080 (6)
I1	0.04594 (11)	0.03372 (10)	0.04233 (11)	−0.00799 (7)	−0.00412 (7)	0.00678 (7)
I2	0.04463 (11)	0.03331 (10)	0.04076 (11)	0.00051 (6)	0.00623 (7)	0.00246 (6)
N1	0.0341 (11)	0.0208 (10)	0.0455 (12)	0.0008 (8)	0.0143 (9)	−0.0006 (8)
N2	0.0591 (15)	0.0290 (11)	0.0312 (11)	0.0031 (10)	−0.0070 (10)	−0.0049 (9)
N3	0.0349 (12)	0.0260 (11)	0.0794 (18)	0.0015 (9)	0.0249 (11)	0.0021 (11)
N4	0.0533 (14)	0.0213 (10)	0.0564 (15)	0.0045 (9)	−0.0226 (11)	−0.0058 (10)
C1	0.0233 (13)	0.0366 (14)	0.112 (3)	−0.0024 (10)	0.0032 (15)	−0.0162 (16)
C2	0.0521 (18)	0.0468 (16)	0.069 (2)	0.0100 (13)	−0.0336 (16)	−0.0153 (15)
C3	0.133 (3)	0.0510 (17)	0.0224 (13)	0.0114 (19)	0.0033 (17)	−0.0005 (12)
C4	0.159 (4)	0.059 (2)	0.048 (2)	0.025 (3)	0.065 (3)	0.0053 (17)
C5	0.087 (3)	0.058 (2)	0.103 (3)	0.0159 (19)	0.074 (3)	0.016 (2)
C6	0.0208 (13)	0.0350 (15)	0.181 (5)	−0.0028 (11)	0.007 (2)	−0.017 (2)
C7	0.0479 (18)	0.0402 (17)	0.116 (3)	0.0065 (13)	−0.041 (2)	−0.0198 (18)
C8	0.123 (3)	0.0407 (15)	0.0269 (14)	0.0178 (18)	−0.0203 (17)	−0.0052 (12)
C9	0.138 (3)	0.0493 (18)	0.0264 (14)	0.036 (2)	0.0204 (18)	0.0019 (13)
C10	0.077 (2)	0.0404 (15)	0.0597 (19)	0.0200 (15)	0.0493 (17)	0.0140 (14)
O1	0.0459 (14)	0.0437 (12)	0.0510 (14)	−0.0005 (10)	−0.0045 (11)	0.0059 (9)

Geometric parameters (Å, º) top

Pd1—N1	2.0307 (19)	C3—H3A	0.9800
Pd1—N3	2.034 (2)	C3—H3B	0.9800
Pd1—N2	2.038 (2)	C4—C5	1.498 (6)
Pd1—N4	2.044 (2)	C4—H4A	0.9800
N1—C10	1.466 (3)	C4—H4B	0.9800
N1—C1	1.487 (4)	C5—H5A	0.9800
N1—H1	0.78 (3)	C5—H5B	0.9800
N2—C3	1.477 (4)	C6—C7	1.487 (6)
N2—C2	1.485 (4)	C6—H6A	0.9800
N2—H2	0.78 (3)	C6—H6B	0.9800
N3—C5	1.467 (5)	C7—H7A	0.9800
N3—C6	1.497 (5)	C7—H7B	0.9800
N3—H3	0.82 (3)	C8—C9	1.503 (5)
N4—C7	1.471 (4)	C8—H8A	0.9800
N4—C8	1.480 (4)	C8—H8B	0.9800
N4—H4	0.78 (3)	C9—C10	1.499 (5)
C1—C2	1.482 (5)	C9—H9A	0.9800
C1—H1A	0.9800	C9—H9B	0.9800
C1—H1B	0.9800	C10—H10A	0.9800
C2—H2A	0.9800	C10—H10B	0.9800
C2—H2B	0.9800	O1—H1O	0.65 (4)
C3—C4	1.518 (6)	O1—H2O	0.79 (4)

N1—Pd1—N3	179.11 (9)	C4—C3—H3B	109.3
N1—Pd1—N2	85.15 (9)	H3A—C3—H3B	107.9
N3—Pd1—N2	95.45 (10)	C5—C4—C3	114.5 (3)
N1—Pd1—N4	94.14 (10)	C5—C4—H4A	108.6
N3—Pd1—N4	85.24 (11)	C3—C4—H4A	108.6
N2—Pd1—N4	178.61 (9)	C5—C4—H4B	108.6
C10—N1—C1	113.6 (3)	C3—C4—H4B	108.6
C10—N1—Pd1	115.25 (18)	H4A—C4—H4B	107.6
C1—N1—Pd1	106.87 (16)	N3—C5—C4	112.6 (3)
C10—N1—H1	106.2 (18)	N3—C5—H5A	109.1
C1—N1—H1	109.3 (19)	C4—C5—H5A	109.1
Pd1—N1—H1	105.2 (19)	N3—C5—H5B	109.1
C3—N2—C2	112.6 (3)	C4—C5—H5B	109.1
C3—N2—Pd1	115.2 (2)	H5A—C5—H5B	107.8
C2—N2—Pd1	106.56 (17)	C7—C6—N3	108.8 (3)
C3—N2—H2	113.1 (19)	C7—C6—H6A	109.9
C2—N2—H2	103 (2)	N3—C6—H6A	109.9
Pd1—N2—H2	105.7 (19)	C7—C6—H6B	109.9
C5—N3—C6	113.5 (3)	N3—C6—H6B	109.9
C5—N3—Pd1	115.8 (2)	H6A—C6—H6B	108.3
C6—N3—Pd1	105.6 (2)	N4—C7—C6	107.5 (3)
C5—N3—H3	109 (2)	N4—C7—H7A	110.2
C6—N3—H3	106 (2)	C6—C7—H7A	110.2
Pd1—N3—H3	106 (2)	N4—C7—H7B	110.2
C7—N4—C8	113.2 (3)	C6—C7—H7B	110.2
C7—N4—Pd1	107.0 (2)	H7A—C7—H7B	108.5
C8—N4—Pd1	116.4 (2)	N4—C8—C9	112.6 (2)
C7—N4—H4	108 (2)	N4—C8—H8A	109.1
C8—N4—H4	108 (2)	C9—C8—H8A	109.1
Pd1—N4—H4	104 (2)	N4—C8—H8B	109.1
C2—C1—N1	108.6 (2)	C9—C8—H8B	109.1
C2—C1—H1A	110.0	H8A—C8—H8B	107.8
N1—C1—H1A	110.0	C10—C9—C8	114.9 (2)
C2—C1—H1B	110.0	C10—C9—H9A	108.5
N1—C1—H1B	110.0	C8—C9—H9A	108.5
H1A—C1—H1B	108.4	C10—C9—H9B	108.5
C1—C2—N2	108.1 (2)	C8—C9—H9B	108.5
C1—C2—H2A	110.1	H9A—C9—H9B	107.5
N2—C2—H2A	110.1	N1—C10—C9	112.1 (3)
C1—C2—H2B	110.1	N1—C10—H10A	109.2
N2—C2—H2B	110.1	C9—C10—H10A	109.2
H2A—C2—H2B	108.4	N1—C10—H10B	109.2
N2—C3—C4	111.8 (3)	C9—C10—H10B	109.2
N2—C3—H3A	109.3	H10A—C10—H10B	107.9
C4—C3—H3A	109.3	H1O—O1—H2O	109 (5)
N2—C3—H3B	109.3

C10—N1—C1—C2	−168.5 (2)	C5—N3—C6—C7	170.2 (3)
Pd1—N1—C1—C2	−40.3 (2)	Pd1—N3—C6—C7	42.3 (3)
N1—C1—C2—N2	55.7 (3)	C8—N4—C7—C6	171.1 (2)
C3—N2—C2—C1	−169.2 (3)	Pd1—N4—C7—C6	41.7 (3)
Pd1—N2—C2—C1	−42.0 (3)	N3—C6—C7—N4	−57.1 (3)
C2—N2—C3—C4	178.9 (3)	C7—N4—C8—C9	−178.7 (3)
Pd1—N2—C3—C4	56.5 (3)	Pd1—N4—C8—C9	−54.2 (3)
N2—C3—C4—C5	−72.1 (4)	N4—C8—C9—C10	68.8 (4)
C6—N3—C5—C4	−178.0 (3)	C1—N1—C10—C9	−176.7 (2)
Pd1—N3—C5—C4	−55.7 (3)	Pd1—N1—C10—C9	59.6 (3)
C3—C4—C5—N3	71.6 (4)	C8—C9—C10—N1	−72.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H2O···I1	0.79 (4)	2.63 (5)	3.405 (3)	169 (4)
O1—H1O···I2	0.65 (4)	2.91 (4)	3.549 (3)	168 (5)
N2—H2···O1ⁱ	0.78 (3)	2.22 (3)	2.993 (3)	173 (3)
N3—H3···I2ⁱⁱ	0.82 (3)	3.02 (3)	3.656 (2)	137 (2)
N4—H4···O1ⁱⁱⁱ	0.78 (3)	2.29 (3)	3.035 (3)	161 (3)

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1, −y+1, −z+1.

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(1,4,8,11-Tetra­aza­cyclo­tetra­deca­ne)palladium(II) diiodide monohydrate

Supporting information

Key indicators

checkCIF/PLATON results

(1,4,8,11-Tetraazacyclotetradecane)palladium(II) diiodide monohydrate