Crystal structure of di­ethyl­ammonium dioxido{Z)-N-[(pyri­din-2-yl)car­bon­yl­azan­idyl]pyri­dine-2-car­box­imid­ato}vana­date(1−) monohydrate

Mondal, B.

doi:10.1107/S2056989024001166

Crystal structure of diethylammonium dioxido{Z)-N-[(pyridin-2-yl)carbonylazanidyl]pyridine-2-carboximidato}vanadate(1−) monohydrate

A new ionic dioxidovanadium(V) compound with an O,N,O donor ligand is reported. In the crystal, extensive hydrogen bonding is observed.

Keywords: crystal structure; dioxidovanadium(V); O,N,O -donor Schiff-base; hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989024001166/ev2002sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989024001166/ev2002Isup2.hkl Contains datablock I

CCDC reference: 2294358

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
Disorder in solvent or counterion
R factor = 0.038
wR factor = 0.110
Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT234_ALERT_4_C Large Hirshfeld Difference N5       --C15B     .       0.16 Ang.
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of         N5 Check
PLAT761_ALERT_1_C CIF Contains no X-H Bonds ......................     Please Check
PLAT762_ALERT_1_C CIF Contains no X-Y-H or H-Y-H Angles ..........     Please Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.969 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
              H5C   H5D
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT300_ALERT_4_G Atom Site Occupancy of C15A       Constrained at        0.7 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C16A       Constrained at        0.7 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C15B       Constrained at        0.3 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C16B       Constrained at        0.3 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15A       Constrained at        0.7 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15B       Constrained at        0.7 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16A       Constrained at        0.7 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16B       Constrained at        0.7 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16C       Constrained at        0.7 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15C       Constrained at        0.3 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15D       Constrained at        0.3 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16D       Constrained at        0.3 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16E       Constrained at        0.3 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H16F       Constrained at        0.3 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd    2)        40% Note
PLAT410_ALERT_2_G Short Intra H...H Contact  H14A     ..H15C     .       1.84 Ang.
                                                      x,y,z  =      1_555 Check
PLAT760_ALERT_1_G CIF Contains no Torsion Angles .................          ? Info
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C4 H12 N
PLAT794_ALERT_5_G Tentative Bond Valency for V1        (V)       .       5.34 Info
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
                0  0  1,
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       3.31 Note
              Predicted wR2: Based on SigI   2  3.32 or SHELX Weight 10.67       
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
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  25 ALERT level G = General information/check it is not something unexpected

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

Computing details top

Diethylammonium dioxido{Z)-N-[(pyridin-2-yl)carbonylazanidyl]pyridine-2-carboximidato}vanadate(1-) monohydrate top

Crystal data top

(C₄H₁₂N)[V(C₁₂H₈N₄O₂)O₂]·H₂O	Z = 2
M_r = 415.32	F(000) = 432
Triclinic, P1	D_x = 1.471 Mg m⁻³
a = 7.6850 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4135 (4) Å	Cell parameters from 9990 reflections
c = 13.9147 (7) Å	θ = 2.3–30.2°
α = 105.609 (2)°	µ = 0.57 mm⁻¹
β = 101.103 (2)°	T = 298 K
γ = 96.253 (2)°	BLOCK, yellow
V = 937.50 (8) Å³	0.32 × 0.18 × 0.03 mm

Data collection top

Bruker D8 Quest with Photon II area detector diffractometer	3852 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.081
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 29.1°, θ_min = 2.3°
T_min = 0.670, T_max = 0.747	h = −10→10
61285 measured reflections	k = −12→12
5048 independent reflections	l = −19→19

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.045P)² + 0.4439P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
5048 reflections	Δρ_max = 0.43 e Å⁻³
274 parameters	Δρ_min = −0.39 e Å⁻³

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
V1	0.58085 (4)	0.29537 (3)	0.78356 (3)	0.03307 (10)
N4	0.0021 (2)	−0.1100 (2)	0.63830 (14)	0.0431 (4)
O2	0.5724 (2)	0.42364 (17)	0.88516 (12)	0.0518 (4)
O3	0.32784 (18)	0.22542 (14)	0.71551 (11)	0.0394 (3)
N3	0.36076 (19)	−0.00629 (16)	0.73136 (13)	0.0332 (3)
C1	0.9836 (3)	0.3489 (2)	0.88556 (17)	0.0419 (5)
H1	0.979921	0.446045	0.882458	0.050*
O1	0.6564 (2)	0.36927 (18)	0.70301 (13)	0.0528 (4)
C2	1.1439 (3)	0.3148 (3)	0.92898 (18)	0.0487 (5)
H2	1.246761	0.387685	0.955215	0.058*
O5	0.8727 (2)	0.6487 (2)	0.7639 (2)	0.0755 (6)
H5C	0.799539	0.566441	0.738019	0.113*
H5D	0.806183	0.714430	0.777364	0.113*
N2	0.53498 (19)	0.07461 (16)	0.77552 (12)	0.0316 (3)
C4	0.9945 (3)	0.0640 (2)	0.89249 (17)	0.0415 (4)
H4	0.996177	−0.034329	0.893312	0.050*
N5	1.2242 (3)	0.6901 (2)	0.72745 (16)	0.0484 (5)
H5A	1.107 (4)	0.694 (3)	0.740 (2)	0.058*
H5B	1.276 (4)	0.777 (3)	0.732 (2)	0.058*
C3	1.1493 (3)	0.1707 (3)	0.93290 (18)	0.0493 (5)
H3	1.256060	0.145211	0.962437	0.059*
O4	0.64803 (19)	−0.13258 (15)	0.80366 (14)	0.0497 (4)
N1	0.8323 (2)	0.24697 (17)	0.84751 (12)	0.0325 (3)
C5	0.8380 (2)	0.1063 (2)	0.85105 (14)	0.0313 (4)
C7	0.2627 (2)	0.08519 (19)	0.70259 (14)	0.0311 (4)
C6	0.6610 (2)	0.00098 (19)	0.80739 (15)	0.0330 (4)
C14	1.3191 (3)	0.6392 (3)	0.8113 (2)	0.0598 (7)
H14A	1.442548	0.635076	0.805965	0.072*
H14B	1.261482	0.539255	0.805202	0.072*
C13	1.3170 (4)	0.7421 (4)	0.9123 (2)	0.0828 (10)
H13A	1.371411	0.841452	0.917594	0.124*
H13B	1.383288	0.709304	0.965860	0.124*
H13C	1.194956	0.742057	0.918946	0.124*
C15A	1.1933 (5)	0.5973 (5)	0.6175 (4)	0.0527 (10)	0.7
H15A	1.112883	0.639100	0.573984	0.063*	0.7
H15B	1.137207	0.496051	0.609451	0.063*	0.7
C16A	1.3721 (7)	0.5944 (7)	0.5852 (5)	0.0695 (13)	0.7
H16A	1.349650	0.557036	0.511873	0.104*	0.7
H16B	1.438875	0.530498	0.615382	0.104*	0.7
H16C	1.440214	0.693958	0.608190	0.104*	0.7
C8	0.0699 (2)	0.0330 (2)	0.65164 (14)	0.0326 (4)
C9	−0.0329 (3)	0.1301 (2)	0.61863 (16)	0.0421 (5)
H9	0.017119	0.229460	0.630326	0.050*
C10	−0.2108 (3)	0.0772 (3)	0.56808 (19)	0.0534 (6)
H10	−0.282243	0.140321	0.544890	0.064*
C11	−0.2801 (3)	−0.0687 (3)	0.55262 (19)	0.0554 (6)
H11	−0.398965	−0.107782	0.517707	0.067*
C12	−0.1699 (3)	−0.1567 (3)	0.58996 (19)	0.0526 (6)
H12	−0.219043	−0.255526	0.580788	0.063*
C15B	1.279 (3)	0.5710 (13)	0.6404 (12)	0.102 (6)	0.3
H15C	1.399256	0.553432	0.665826	0.123*	0.3
H15D	1.196845	0.477106	0.621828	0.123*	0.3
C16B	1.276 (3)	0.6182 (19)	0.5559 (13)	0.116 (6)	0.3
H16D	1.270778	0.533969	0.497547	0.173*	0.3
H16E	1.383543	0.688974	0.567037	0.173*	0.3
H16F	1.172786	0.664919	0.543386	0.173*	0.3

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.03157 (16)	0.02325 (15)	0.04138 (19)	0.00202 (11)	0.00358 (13)	0.00908 (12)
N4	0.0319 (8)	0.0415 (9)	0.0525 (11)	−0.0027 (7)	0.0019 (7)	0.0175 (8)
O2	0.0457 (8)	0.0400 (8)	0.0543 (9)	0.0124 (7)	−0.0010 (7)	−0.0046 (7)
O3	0.0345 (7)	0.0278 (6)	0.0520 (8)	0.0024 (5)	−0.0009 (6)	0.0141 (6)
N3	0.0249 (7)	0.0277 (7)	0.0438 (9)	−0.0003 (6)	0.0023 (6)	0.0111 (6)
C1	0.0354 (10)	0.0326 (9)	0.0495 (12)	−0.0043 (8)	0.0055 (9)	0.0056 (9)
O1	0.0511 (9)	0.0474 (9)	0.0672 (11)	0.0019 (7)	0.0118 (8)	0.0329 (8)
C2	0.0319 (10)	0.0489 (12)	0.0526 (13)	−0.0062 (9)	0.0018 (9)	0.0049 (10)
O5	0.0432 (9)	0.0467 (10)	0.146 (2)	0.0060 (8)	0.0276 (11)	0.0400 (12)
N2	0.0239 (7)	0.0261 (7)	0.0422 (9)	0.0002 (5)	0.0031 (6)	0.0106 (6)
C4	0.0325 (9)	0.0428 (11)	0.0485 (12)	0.0072 (8)	0.0035 (8)	0.0163 (9)
N5	0.0555 (12)	0.0325 (9)	0.0583 (12)	0.0029 (8)	0.0163 (10)	0.0151 (9)
C3	0.0294 (10)	0.0594 (14)	0.0536 (13)	0.0053 (9)	−0.0009 (9)	0.0162 (11)
O4	0.0362 (7)	0.0312 (7)	0.0835 (12)	0.0050 (6)	0.0057 (7)	0.0260 (7)
N1	0.0288 (7)	0.0288 (7)	0.0371 (8)	0.0010 (6)	0.0065 (6)	0.0076 (6)
C5	0.0283 (8)	0.0318 (9)	0.0339 (9)	0.0043 (7)	0.0067 (7)	0.0108 (7)
C7	0.0306 (8)	0.0289 (8)	0.0324 (9)	0.0018 (7)	0.0058 (7)	0.0090 (7)
C6	0.0320 (9)	0.0262 (8)	0.0399 (10)	0.0035 (7)	0.0040 (7)	0.0119 (7)
C14	0.0450 (12)	0.0587 (15)	0.098 (2)	0.0169 (11)	0.0232 (13)	0.0522 (15)
C13	0.072 (2)	0.124 (3)	0.0664 (19)	0.0195 (19)	0.0103 (15)	0.054 (2)
C15A	0.049 (2)	0.041 (2)	0.059 (3)	0.0063 (15)	0.0060 (18)	0.0045 (17)
C16A	0.066 (3)	0.077 (3)	0.065 (3)	0.019 (2)	0.023 (2)	0.011 (2)
C8	0.0296 (8)	0.0355 (9)	0.0317 (9)	0.0034 (7)	0.0066 (7)	0.0095 (7)
C9	0.0372 (10)	0.0438 (11)	0.0438 (11)	0.0103 (8)	0.0046 (8)	0.0127 (9)
C10	0.0353 (11)	0.0700 (16)	0.0564 (14)	0.0171 (11)	0.0032 (10)	0.0232 (12)
C11	0.0260 (9)	0.0803 (17)	0.0554 (14)	0.0011 (10)	0.0004 (9)	0.0221 (13)
C12	0.0344 (11)	0.0547 (13)	0.0609 (15)	−0.0099 (9)	0.0015 (10)	0.0178 (11)
C15B	0.179 (19)	0.039 (5)	0.083 (10)	0.028 (9)	0.019 (12)	0.013 (6)
C16B	0.137 (17)	0.088 (10)	0.111 (14)	0.029 (11)	0.046 (13)	−0.005 (9)

Geometric parameters (Å, º) top

V1—O2	1.6107 (15)	C4—C5	1.378 (3)
V1—O3	1.9461 (14)	N5—C14	1.473 (3)
V1—O1	1.6310 (16)	N5—C15A	1.502 (5)
V1—N2	2.0385 (15)	N5—C15B	1.573 (16)
V1—N1	2.1170 (15)	O4—C6	1.237 (2)
N4—C8	1.340 (2)	N1—C5	1.343 (2)
N4—C12	1.329 (3)	C5—C6	1.506 (2)
O3—C7	1.311 (2)	C7—C8	1.480 (2)
N3—N2	1.400 (2)	C14—C13	1.481 (4)
N3—C7	1.296 (2)	C15A—C16A	1.526 (7)
C1—C2	1.375 (3)	C8—C9	1.383 (3)
C1—N1	1.342 (2)	C9—C10	1.380 (3)
C2—C3	1.377 (3)	C10—C11	1.362 (4)
N2—C6	1.327 (2)	C11—C12	1.374 (3)
C4—C3	1.385 (3)	C15B—C16B	1.36 (2)

O2—V1—O3	102.55 (7)	C1—N1—V1	123.69 (13)
O2—V1—O1	110.64 (9)	C1—N1—C5	118.88 (16)
O2—V1—N2	121.01 (8)	C5—N1—V1	117.43 (12)
O2—V1—N1	95.14 (7)	C4—C5—C6	123.33 (17)
O3—V1—N2	74.82 (5)	N1—C5—C4	121.92 (17)
O3—V1—N1	148.99 (6)	N1—C5—C6	114.75 (15)
O1—V1—O3	102.22 (7)	O3—C7—C8	117.03 (15)
O1—V1—N2	127.77 (8)	N3—C7—O3	122.55 (16)
O1—V1—N1	94.92 (7)	N3—C7—C8	120.41 (16)
N2—V1—N1	74.24 (6)	N2—C6—C5	109.38 (15)
C12—N4—C8	116.92 (18)	O4—C6—N2	129.15 (17)
C7—O3—V1	117.29 (11)	O4—C6—C5	121.47 (16)
C7—N3—N2	106.98 (14)	N5—C14—C13	110.7 (2)
N1—C1—C2	122.3 (2)	N5—C15A—C16A	109.9 (3)
C1—C2—C3	118.8 (2)	N4—C8—C7	117.44 (16)
N3—N2—V1	118.33 (10)	N4—C8—C9	122.41 (18)
C6—N2—V1	124.19 (12)	C9—C8—C7	120.14 (17)
C6—N2—N3	117.46 (14)	C10—C9—C8	119.0 (2)
C5—C4—C3	118.71 (19)	C11—C10—C9	119.1 (2)
C14—N5—C15A	120.9 (2)	C10—C11—C12	118.2 (2)
C14—N5—C15B	94.6 (6)	N4—C12—C11	124.4 (2)
C2—C3—C4	119.43 (19)	C16B—C15B—N5	111.2 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O5	0.95 (3)	1.92 (3)	2.848 (3)	165 (3)
N5—H5B···N3ⁱ	0.85 (3)	2.08 (3)	2.918 (3)	171 (3)
O5—H5C···O1	0.85	1.94	2.776 (3)	169
O5—H5D···O4ⁱⁱ	0.85	1.99	2.838 (2)	178
C2—H2···O2ⁱⁱⁱ	0.93	2.48	3.277 (3)	143
C14—H14A···O4ⁱ	0.97	2.57	3.172 (3)	121
C15A—H15A···N4ⁱ	0.97	2.59	3.233 (5)	124

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

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Crystal structure of di­ethyl­ammonium dioxido{Z)-N-[(pyri­din-2-yl)car­bon­yl­azan­idyl]pyri­dine-2-car­box­imid­ato}vana­date(1−) monohydrate

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure of diethylammonium dioxido{Z)-N-[(pyridin-2-yl)carbonylazanidyl]pyridine-2-carboximidato}vanadate(1−) monohydrate