Crystal structures of a series of bis­(acetyl­aceto­nato)oxovanadium(IV) complexes containing N-donor pyridyl ligands

Three six-coordinate complexes of bis­(acetyl­acetonato)oxovanadium(IV) containing N-donating pyridyl ligands are reported. Both cis and trans isomers were isolated and characterized from these systems.

Key indicators

Structure: compound1

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.027
• wR factor = 0.073
• Data-to-parameter ratio = 19.6

Structure: compound2

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.027
• wR factor = 0.071
• Data-to-parameter ratio = 17.9

Structure: compound3

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.030
• wR factor = 0.081
• Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Datablock: compound1



Alert level G
PLAT794_ALERT_5_G Tentative Bond Valency for V1        (IV)      .       4.13 Info
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

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

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




Datablock: compound2



Alert level G
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3 Note
PLAT794_ALERT_5_G Tentative Bond Valency for V1        (IV)      .       4.13 Info
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

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

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




Datablock: compound3



Alert level G
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V1       --O1       .        7.8 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V1       --O4       .        5.2 s.u.
PLAT432_ALERT_2_G Short Inter X...Y Contact  C3       ..C14              3.20 Ang.
                                                1-x,1-y,1-z  =      3_666 Check
PLAT794_ALERT_5_G Tentative Bond Valency for V1        (IV)      .       4.10 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         14 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

For all structures, data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: XP (Bruker, 2015) and Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

Bis(acetylacetonato-κ²O,O')oxido(pyridine-κN)vanadium(IV) (compound1)

Crystal data

[V(C5H7O2)2O(C5H5N)]	F(000) = 716
Mr = 344.25	Dx = 1.402 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.8820 (5) Å	Cell parameters from 8119 reflections
b = 15.2092 (11) Å	θ = 2.7–28.3°
c = 13.9871 (9) Å	µ = 0.63 mm^−1
β = 103.367 (2)°	T = 120 K
V = 1631.33 (19) Å^3	Tablet, blue
Z = 4	0.23 × 0.14 × 0.11 mm

Data collection

Bruker APEXII diffractometer	2037 independent reflections
Radiation source: fine-focus sealed tube	1882 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm^-1	Rint = 0.025
combination of ω and φ–scans	θmax = 28.3°, θmin = 2.7°
Absorption correction: numerical (SADABS; Krause et al., 2015)	h = −10→10
Tmin = 0.912, Tmax = 0.966	k = −20→20
17837 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0362P)^2 + 1.4639P] where P = (Fo^2 + 2Fc^2)/3
2037 reflections	(Δ/σ)max < 0.001
104 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
V1	0.500000	0.41643 (2)	0.750000	0.01694 (10)
O1	0.500000	0.52179 (9)	0.750000	0.0239 (3)
O2	0.54371 (12)	0.39403 (6)	0.61740 (7)	0.0211 (2)
O3	0.24437 (11)	0.39799 (6)	0.69551 (7)	0.0212 (2)
N1	0.500000	0.25955 (10)	0.750000	0.0193 (3)
C1	0.43127 (17)	0.37920 (9)	0.53797 (9)	0.0209 (3)
C2	0.25102 (18)	0.37547 (10)	0.52875 (10)	0.0264 (3)
H2	0.179805	0.365061	0.465064	0.032*
C3	0.16766 (17)	0.38580 (8)	0.60560 (10)	0.0211 (3)
C4	−0.02841 (18)	0.38382 (11)	0.58352 (12)	0.0312 (3)
H4A	−0.066433	0.356674	0.638591	0.047*
H4B	−0.072855	0.349511	0.523659	0.047*
H4C	−0.073646	0.443987	0.573924	0.047*
C5	0.5033 (2)	0.36549 (12)	0.44857 (11)	0.0322 (3)
H5A	0.542558	0.421933	0.427631	0.048*
H5B	0.412268	0.340944	0.395398	0.048*
H5C	0.601990	0.324655	0.464361	0.048*
C6	0.37706 (16)	0.21376 (9)	0.78046 (9)	0.0224 (3)
H6	0.289206	0.245242	0.802491	0.027*
C7	0.37197 (19)	0.12280 (10)	0.78135 (10)	0.0274 (3)
H7	0.282169	0.092712	0.803098	0.033*
C8	0.500000	0.07661 (13)	0.750000	0.0293 (4)
H8	0.500002	0.014145	0.750000	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
V1	0.01327 (15)	0.02129 (16)	0.01593 (15)	0.000	0.00271 (10)	0.000
O1	0.0223 (6)	0.0235 (7)	0.0260 (7)	0.000	0.0059 (5)	0.000
O2	0.0176 (4)	0.0282 (5)	0.0176 (4)	−0.0010 (3)	0.0040 (3)	0.0010 (3)
O3	0.0142 (4)	0.0279 (5)	0.0207 (4)	0.0012 (3)	0.0021 (3)	−0.0002 (4)
N1	0.0155 (7)	0.0221 (7)	0.0198 (7)	0.000	0.0033 (5)	0.000
C1	0.0230 (6)	0.0206 (6)	0.0185 (6)	0.0018 (5)	0.0037 (5)	0.0021 (5)
C2	0.0206 (6)	0.0354 (8)	0.0203 (6)	0.0013 (5)	−0.0014 (5)	−0.0029 (5)
C3	0.0170 (6)	0.0195 (6)	0.0249 (6)	0.0011 (4)	0.0004 (5)	0.0001 (5)
C4	0.0163 (6)	0.0408 (8)	0.0333 (8)	0.0005 (6)	−0.0004 (6)	−0.0075 (6)
C5	0.0312 (8)	0.0463 (9)	0.0195 (6)	0.0008 (7)	0.0069 (6)	−0.0013 (6)
C6	0.0170 (6)	0.0276 (7)	0.0227 (6)	−0.0019 (5)	0.0047 (5)	−0.0003 (5)
C7	0.0286 (7)	0.0284 (7)	0.0244 (7)	−0.0090 (5)	0.0043 (5)	0.0005 (5)
C8	0.0403 (12)	0.0217 (9)	0.0228 (9)	0.000	0.0013 (8)	0.000

Geometric parameters (Å, º)

V1—O1	1.6024 (14)	C2—H2	0.9500
V1—O2	1.9925 (9)	C3—C4	1.5047 (18)
V1—O2^i	1.9925 (9)	C4—H4A	0.9800
V1—O3^i	2.0023 (9)	C4—H4B	0.9800
V1—O3	2.0023 (9)	C4—H4C	0.9800
V1—N1	2.3861 (16)	C5—H5A	0.9800
O2—C1	1.2710 (16)	C5—H5B	0.9800
O3—C3	1.2766 (16)	C5—H5C	0.9800
N1—C6	1.3402 (15)	C6—C7	1.384 (2)
N1—C6^i	1.3402 (15)	C6—H6	0.9500
C1—C2	1.3977 (19)	C7—C8	1.3816 (18)
C1—C5	1.5025 (19)	C7—H7	0.9500
C2—C3	1.392 (2)	C8—H8	0.9500
O1—V1—O2	99.84 (3)	C1—C2—H2	117.4
O1—V1—O2^i	99.85 (3)	O3—C3—C2	125.19 (12)
O2—V1—O2^i	160.31 (6)	O3—C3—C4	115.80 (12)
O1—V1—O3^i	98.05 (3)	C2—C3—C4	119.01 (12)
O2—V1—O3^i	87.43 (4)	C3—C4—H4A	109.5
O2^i—V1—O3^i	89.83 (4)	C3—C4—H4B	109.5
O1—V1—O3	98.05 (3)	H4A—C4—H4B	109.5
O2—V1—O3	89.83 (4)	C3—C4—H4C	109.5
O2^i—V1—O3	87.42 (4)	H4A—C4—H4C	109.5
O3^i—V1—O3	163.90 (6)	H4B—C4—H4C	109.5
O1—V1—N1	180.0	C1—C5—H5A	109.5
O2—V1—N1	80.16 (3)	C1—C5—H5B	109.5
O2^i—V1—N1	80.15 (3)	H5A—C5—H5B	109.5
O3^i—V1—N1	81.95 (3)	C1—C5—H5C	109.5
O3—V1—N1	81.95 (3)	H5A—C5—H5C	109.5
C1—O2—V1	127.47 (9)	H5B—C5—H5C	109.5
C3—O3—V1	126.95 (9)	N1—C6—C7	123.15 (13)
C6—N1—C6^i	117.39 (16)	N1—C6—H6	118.4
C6—N1—V1	121.31 (8)	C7—C6—H6	118.4
C6^i—N1—V1	121.30 (8)	C8—C7—C6	118.72 (14)
O2—C1—C2	125.19 (12)	C8—C7—H7	120.6
O2—C1—C5	115.52 (12)	C6—C7—H7	120.6
C2—C1—C5	119.28 (12)	C7—C8—C7^i	118.87 (19)
C3—C2—C1	125.12 (13)	C7—C8—H8	120.6
C3—C2—H2	117.4	C7^i—C8—H8	120.6
V1—O2—C1—C2	−0.2 (2)	C1—C2—C3—O3	−1.8 (2)
V1—O2—C1—C5	179.40 (9)	C1—C2—C3—C4	177.47 (13)
O2—C1—C2—C3	−1.3 (2)	C6^i—N1—C6—C7	−0.21 (9)
C5—C1—C2—C3	179.11 (14)	V1—N1—C6—C7	179.79 (9)
V1—O3—C3—C2	5.89 (19)	N1—C6—C7—C8	0.41 (18)
V1—O3—C3—C4	−173.40 (9)	C6—C7—C8—C7^i	−0.19 (9)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1^ii	0.98	2.58	3.2589 (18)	127
C7—H7···O1^iii	0.95	2.43	3.2487 (17)	144

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

Bis(acetylacetonato-κ²O,O')oxido(pyridine-4-carbonitrile-κN)vanadium(IV) (compound2)

Crystal data

[V(C5H7O2)2O(C6H4N2)]	F(000) = 764
Mr = 369.26	Dx = 1.496 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.1930 (9) Å	Cell parameters from 7973 reflections
b = 13.5080 (9) Å	θ = 2.7–28.1°
c = 13.3651 (9) Å	µ = 0.63 mm^−1
β = 99.030 (3)°	T = 120 K
V = 1639.1 (2) Å^3	Block, green
Z = 4	0.15 × 0.11 × 0.07 mm

Data collection

Bruker APEXII diffractometer	2038 independent reflections
Radiation source: fine-focus sealed tube	1832 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm^-1	Rint = 0.032
combination of ω and φ–scans	θmax = 28.3°, θmin = 2.7°
Absorption correction: numerical (SADABS; Krause et al., 2015)	h = −12→12
Tmin = 0.927, Tmax = 0.980	k = −18→18
21763 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.071	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0324P)^2 + 1.6979P] where P = (Fo^2 + 2Fc^2)/3
2038 reflections	(Δ/σ)max = 0.001
114 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
V1	0.500000	0.89112 (2)	0.750000	0.01271 (10)
O1	0.500000	1.00987 (10)	0.750000	0.0210 (3)
O2	0.60596 (10)	0.86813 (7)	0.63185 (7)	0.0166 (2)
O3	0.31046 (10)	0.86962 (7)	0.65896 (7)	0.0151 (2)
N1	0.500000	0.71328 (11)	0.750000	0.0130 (3)
N2	0.500000	0.31564 (14)	0.750000	0.0318 (4)
C1	0.54997 (15)	0.87153 (9)	0.53874 (10)	0.0157 (3)
C2	0.39870 (16)	0.87878 (10)	0.50203 (10)	0.0195 (3)
H2	0.369478	0.886023	0.431015	0.023*
C3	0.28850 (15)	0.87607 (9)	0.56257 (10)	0.0155 (3)
C4	0.65451 (16)	0.86478 (11)	0.46315 (11)	0.0214 (3)
H4A	0.653674	0.797228	0.436328	0.032*
H4B	0.754227	0.881506	0.496340	0.032*
H4C	0.623837	0.911208	0.407492	0.032*
C5	0.12947 (16)	0.88186 (11)	0.51467 (11)	0.0223 (3)
H5A	0.121409	0.870964	0.441516	0.033*
H5B	0.090305	0.947415	0.527156	0.033*
H5C	0.073029	0.830993	0.544114	0.033*
C6	0.37746 (14)	0.66216 (10)	0.75924 (9)	0.0148 (3)
H6	0.290548	0.697948	0.765924	0.018*
C7	0.37194 (14)	0.55958 (10)	0.75947 (10)	0.0164 (3)
H7	0.283303	0.525726	0.765917	0.020*
C8	0.500000	0.50744 (14)	0.750000	0.0161 (4)
C9	0.500000	0.40014 (15)	0.750000	0.0222 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
V1	0.01153 (15)	0.01478 (16)	0.01141 (15)	0.000	0.00052 (11)	0.000
O1	0.0213 (7)	0.0169 (7)	0.0235 (7)	0.000	−0.0005 (6)	0.000
O2	0.0149 (4)	0.0214 (5)	0.0137 (4)	0.0006 (3)	0.0032 (4)	0.0027 (3)
O3	0.0127 (4)	0.0194 (5)	0.0126 (4)	0.0007 (3)	0.0002 (3)	0.0002 (3)
N1	0.0133 (7)	0.0150 (7)	0.0108 (7)	0.000	0.0026 (5)	0.000
N2	0.0394 (11)	0.0174 (9)	0.0429 (12)	0.000	0.0196 (9)	0.000
C1	0.0198 (6)	0.0124 (6)	0.0158 (6)	0.0018 (5)	0.0055 (5)	0.0022 (4)
C2	0.0215 (7)	0.0261 (7)	0.0108 (6)	0.0043 (5)	0.0016 (5)	0.0008 (5)
C3	0.0170 (6)	0.0136 (6)	0.0150 (6)	0.0023 (4)	−0.0009 (5)	−0.0013 (5)
C4	0.0248 (7)	0.0232 (7)	0.0179 (7)	0.0058 (5)	0.0092 (6)	0.0039 (5)
C5	0.0171 (6)	0.0310 (8)	0.0168 (7)	0.0039 (5)	−0.0031 (5)	−0.0014 (6)
C6	0.0134 (6)	0.0181 (6)	0.0135 (6)	0.0005 (5)	0.0035 (5)	0.0003 (5)
C7	0.0162 (6)	0.0186 (6)	0.0151 (6)	−0.0032 (5)	0.0044 (5)	0.0001 (5)
C8	0.0219 (9)	0.0148 (9)	0.0121 (8)	0.000	0.0042 (7)	0.000
C9	0.0257 (10)	0.0212 (10)	0.0218 (10)	0.000	0.0107 (8)	0.000

Geometric parameters (Å, º)

V1—O1	1.6040 (14)	C2—H2	0.9500
V1—O3^i	1.9838 (9)	C3—C5	1.5031 (18)
V1—O3	1.9838 (9)	C4—H4A	0.9800
V1—O2^i	2.0055 (9)	C4—H4B	0.9800
V1—O2	2.0055 (9)	C4—H4C	0.9800
V1—N1	2.4022 (15)	C5—H5A	0.9800
O2—C1	1.2706 (17)	C5—H5B	0.9800
O3—C3	1.2752 (17)	C5—H5C	0.9800
N1—C6	1.3435 (15)	C6—C7	1.3866 (19)
N1—C6^i	1.3435 (15)	C6—H6	0.9500
N2—C9	1.141 (3)	C7—C8	1.3946 (16)
C1—C2	1.4035 (19)	C7—H7	0.9500
C1—C4	1.5024 (18)	C8—C9	1.449 (3)
C2—C3	1.3928 (19)
O1—V1—O3^i	98.42 (3)	O3—C3—C2	125.06 (13)
O1—V1—O3	98.42 (3)	O3—C3—C5	115.03 (12)
O3^i—V1—O3	163.17 (6)	C2—C3—C5	119.91 (12)
O1—V1—O2^i	98.91 (3)	C1—C4—H4A	109.5
O3^i—V1—O2^i	89.01 (4)	C1—C4—H4B	109.5
O3—V1—O2^i	88.39 (4)	H4A—C4—H4B	109.5
O1—V1—O2	98.91 (3)	C1—C4—H4C	109.5
O3^i—V1—O2	88.39 (4)	H4A—C4—H4C	109.5
O3—V1—O2	89.01 (4)	H4B—C4—H4C	109.5
O2^i—V1—O2	162.19 (6)	C3—C5—H5A	109.5
O1—V1—N1	180.0	C3—C5—H5B	109.5
O3^i—V1—N1	81.58 (3)	H5A—C5—H5B	109.5
O3—V1—N1	81.58 (3)	C3—C5—H5C	109.5
O2^i—V1—N1	81.09 (3)	H5A—C5—H5C	109.5
O2—V1—N1	81.09 (3)	H5B—C5—H5C	109.5
C1—O2—V1	126.40 (9)	N1—C6—C7	123.05 (12)
C3—O3—V1	126.45 (9)	N1—C6—H6	118.5
C6—N1—C6^i	118.13 (15)	C7—C6—H6	118.5
C6—N1—V1	120.93 (8)	C6—C7—C8	118.22 (12)
C6^i—N1—V1	120.93 (8)	C6—C7—H7	120.9
O2—C1—C2	124.87 (12)	C8—C7—H7	120.9
O2—C1—C4	116.92 (12)	C7^i—C8—C7	119.33 (17)
C2—C1—C4	118.19 (12)	C7^i—C8—C9	120.33 (8)
C3—C2—C1	124.49 (13)	C7—C8—C9	120.33 (8)
C3—C2—H2	117.8	N2—C9—C8	180.0
C1—C2—H2	117.8
V1—O2—C1—C2	−9.23 (18)	C1—C2—C3—C5	−178.42 (13)
V1—O2—C1—C4	172.30 (9)	C6^i—N1—C6—C7	−0.12 (9)
O2—C1—C2—C3	−4.8 (2)	V1—N1—C6—C7	179.88 (9)
C4—C1—C2—C3	173.61 (13)	N1—C6—C7—C8	0.22 (17)
V1—O3—C3—C2	14.38 (18)	C6—C7—C8—C7^i	−0.11 (8)
V1—O3—C3—C5	−165.06 (9)	C6—C7—C8—C9	179.89 (8)
C1—C2—C3—O3	2.2 (2)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4C···O1^ii	0.98	2.47	3.4249 (16)	164
C7—H7···O1^iii	0.95	2.59	3.4673 (14)	154

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

Bis(acetylacetonato-κ²O,O')(4-methoxypyridine-κN)oxidovanadium(IV) (compound3)

Crystal data

[V(C5H7O2)2O(C6H7NO)]	F(000) = 780
Mr = 374.28	Dx = 1.403 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.6619 (15) Å	Cell parameters from 9171 reflections
b = 11.9922 (19) Å	θ = 2.4–28.3°
c = 15.344 (2) Å	µ = 0.59 mm^−1
β = 94.651 (2)°	T = 120 K
V = 1772.0 (5) Å^3	Block, blue
Z = 4	0.32 × 0.19 × 0.11 mm

Data collection

Bruker Kappa X8-APEXII diffractometer	4413 independent reflections
Radiation source: fine-focus sealed tube	3730 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 8.33 pixels mm^-1	θmax = 28.4°, θmin = 2.2°
combination of ω and φ–scans	h = −12→12
Absorption correction: numerical (SADABS; Krause et al., 2015)	k = −16→16
Tmin = 0.862, Tmax = 0.983	l = −20→20
25688 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.081	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0348P)^2 + 1.1201P] where P = (Fo^2 + 2Fc^2)/3
4413 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
V1	0.46984 (2)	0.46573 (2)	0.27536 (2)	0.01335 (7)
O1	0.53209 (11)	0.36808 (9)	0.21879 (7)	0.0206 (2)
O2	0.52992 (10)	0.59883 (9)	0.20819 (6)	0.0187 (2)
O3	0.63443 (10)	0.49106 (8)	0.36048 (7)	0.0167 (2)
O4	0.37408 (11)	0.59132 (8)	0.35341 (7)	0.0175 (2)
O5	0.28270 (11)	0.46703 (8)	0.20760 (6)	0.0173 (2)
O6	0.26958 (12)	0.12492 (9)	0.54929 (7)	0.0244 (2)
N1	0.39173 (13)	0.35591 (10)	0.37014 (8)	0.0153 (2)
C1	0.63492 (16)	0.66210 (12)	0.22605 (10)	0.0185 (3)
C2	0.73408 (16)	0.64880 (13)	0.29670 (10)	0.0198 (3)
H2	0.809349	0.699961	0.302343	0.024*
C3	0.72947 (15)	0.56495 (12)	0.35957 (9)	0.0161 (3)
C4	0.84276 (16)	0.55651 (13)	0.43262 (10)	0.0222 (3)
H4A	0.801910	0.538371	0.487292	0.033*
H4B	0.891915	0.627884	0.439042	0.033*
H4C	0.908201	0.497767	0.419094	0.033*
C5	0.6492 (2)	0.75837 (15)	0.16467 (12)	0.0334 (4)
H5A	0.656443	0.730050	0.105296	0.050*
H5B	0.732960	0.801013	0.183335	0.050*
H5C	0.567632	0.806796	0.165362	0.050*
C6	0.24885 (15)	0.62275 (12)	0.35059 (9)	0.0167 (3)
C7	0.14287 (16)	0.58216 (14)	0.29076 (10)	0.0215 (3)
H7	0.050317	0.605404	0.297396	0.026*
C8	0.16543 (16)	0.51020 (13)	0.22263 (10)	0.0193 (3)
C9	0.21222 (17)	0.71170 (13)	0.41458 (10)	0.0226 (3)
H9A	0.242406	0.687897	0.474206	0.034*
H9B	0.111497	0.723372	0.409565	0.034*
H9C	0.258989	0.781507	0.401452	0.034*
C10	0.04535 (18)	0.47785 (17)	0.15869 (12)	0.0320 (4)
H10A	0.069407	0.492688	0.098957	0.048*
H10B	−0.036755	0.521553	0.170540	0.048*
H10C	0.025355	0.398275	0.165035	0.048*
C11	0.28395 (15)	0.28757 (12)	0.34893 (9)	0.0177 (3)
H11	0.238256	0.293682	0.291934	0.021*
C12	0.23542 (15)	0.20886 (12)	0.40496 (10)	0.0184 (3)
H12	0.157914	0.163143	0.387202	0.022*
C13	0.30337 (15)	0.19861 (12)	0.48803 (9)	0.0171 (3)
C14	0.41468 (15)	0.26970 (12)	0.51178 (9)	0.0178 (3)
H14	0.462236	0.265216	0.568336	0.021*
C15	0.45407 (15)	0.34604 (12)	0.45204 (9)	0.0174 (3)
H15	0.529131	0.394613	0.469025	0.021*
C16	0.15152 (19)	0.05480 (15)	0.52768 (11)	0.0289 (4)
H16A	0.069247	0.101227	0.513676	0.043*
H16B	0.136044	0.006690	0.577595	0.043*
H16C	0.168604	0.008556	0.476993	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
V1	0.01255 (12)	0.01250 (12)	0.01468 (12)	−0.00034 (9)	−0.00089 (8)	0.00034 (8)
O1	0.0192 (5)	0.0202 (5)	0.0224 (5)	0.0020 (4)	0.0010 (4)	−0.0016 (4)
O2	0.0180 (5)	0.0185 (5)	0.0191 (5)	−0.0031 (4)	−0.0018 (4)	0.0043 (4)
O3	0.0132 (5)	0.0166 (5)	0.0196 (5)	−0.0025 (4)	−0.0022 (4)	0.0028 (4)
O4	0.0155 (5)	0.0173 (5)	0.0190 (5)	0.0005 (4)	−0.0022 (4)	−0.0022 (4)
O5	0.0162 (5)	0.0176 (5)	0.0173 (5)	−0.0002 (4)	−0.0031 (4)	−0.0015 (4)
O6	0.0245 (6)	0.0265 (6)	0.0216 (5)	−0.0115 (5)	−0.0014 (4)	0.0063 (4)
N1	0.0151 (6)	0.0142 (5)	0.0163 (6)	−0.0009 (5)	−0.0007 (4)	0.0001 (4)
C1	0.0189 (7)	0.0172 (7)	0.0199 (7)	−0.0017 (6)	0.0035 (6)	0.0020 (5)
C2	0.0164 (7)	0.0199 (7)	0.0230 (7)	−0.0051 (6)	0.0019 (6)	0.0003 (6)
C3	0.0132 (6)	0.0170 (6)	0.0182 (7)	0.0004 (5)	0.0013 (5)	−0.0024 (5)
C4	0.0160 (7)	0.0246 (8)	0.0250 (8)	−0.0026 (6)	−0.0047 (6)	−0.0006 (6)
C5	0.0366 (10)	0.0311 (9)	0.0315 (9)	−0.0130 (8)	−0.0041 (7)	0.0151 (7)
C6	0.0172 (7)	0.0167 (7)	0.0162 (6)	0.0002 (5)	0.0022 (5)	0.0026 (5)
C7	0.0129 (7)	0.0282 (8)	0.0233 (7)	0.0017 (6)	−0.0003 (6)	−0.0023 (6)
C8	0.0147 (7)	0.0217 (7)	0.0207 (7)	−0.0014 (6)	−0.0029 (5)	0.0015 (6)
C9	0.0224 (8)	0.0238 (8)	0.0218 (7)	0.0028 (6)	0.0029 (6)	−0.0042 (6)
C10	0.0188 (8)	0.0435 (11)	0.0320 (9)	0.0003 (7)	−0.0087 (7)	−0.0111 (8)
C11	0.0186 (7)	0.0173 (7)	0.0165 (7)	−0.0031 (6)	−0.0035 (5)	−0.0013 (5)
C12	0.0169 (7)	0.0176 (7)	0.0201 (7)	−0.0046 (6)	−0.0011 (5)	−0.0022 (5)
C13	0.0174 (7)	0.0162 (6)	0.0178 (7)	−0.0015 (5)	0.0025 (5)	0.0007 (5)
C14	0.0166 (7)	0.0202 (7)	0.0160 (6)	−0.0022 (6)	−0.0020 (5)	0.0003 (5)
C15	0.0159 (7)	0.0180 (7)	0.0176 (7)	−0.0035 (6)	−0.0023 (5)	−0.0013 (5)
C16	0.0308 (9)	0.0289 (9)	0.0271 (8)	−0.0160 (7)	0.0030 (7)	0.0037 (7)

Geometric parameters (Å, º)

V1—O1	1.6035 (11)	C5—H5C	0.9800
V1—O3	1.9975 (10)	C6—C7	1.406 (2)
V1—O2	2.0110 (11)	C6—C9	1.511 (2)
V1—O5	2.0115 (10)	C7—C8	1.386 (2)
V1—N1	2.1440 (12)	C7—H7	0.9500
V1—O4	2.1767 (11)	C8—C10	1.508 (2)
O2—C1	1.2786 (18)	C9—H9A	0.9800
O3—C3	1.2770 (17)	C9—H9B	0.9800
O4—C6	1.2647 (18)	C9—H9C	0.9800
O5—C8	1.2835 (18)	C10—H10A	0.9800
O6—C13	1.3494 (17)	C10—H10B	0.9800
O6—C16	1.4342 (19)	C10—H10C	0.9800
N1—C11	1.3442 (18)	C11—C12	1.384 (2)
N1—C15	1.3541 (18)	C11—H11	0.9500
C1—C2	1.396 (2)	C12—C13	1.391 (2)
C1—C5	1.503 (2)	C12—H12	0.9500
C2—C3	1.397 (2)	C13—C14	1.397 (2)
C2—H2	0.9500	C14—C15	1.371 (2)
C3—C4	1.505 (2)	C14—H14	0.9500
C4—H4A	0.9800	C15—H15	0.9500
C4—H4B	0.9800	C16—H16A	0.9800
C4—H4C	0.9800	C16—H16B	0.9800
C5—H5A	0.9800	C16—H16C	0.9800
C5—H5B	0.9800
O1—V1—O3	98.71 (5)	H5B—C5—H5C	109.5
O1—V1—O2	99.54 (5)	O4—C6—C7	124.29 (14)
O3—V1—O2	88.10 (4)	O4—C6—C9	117.52 (13)
O1—V1—O5	94.97 (5)	C7—C6—C9	118.18 (13)
O3—V1—O5	166.27 (4)	C8—C7—C6	123.87 (14)
O2—V1—O5	90.78 (4)	C8—C7—H7	118.1
O1—V1—N1	94.97 (5)	C6—C7—H7	118.1
O3—V1—N1	87.44 (4)	O5—C8—C7	125.57 (13)
O2—V1—N1	165.31 (5)	O5—C8—C10	115.03 (14)
O5—V1—N1	90.24 (5)	C7—C8—C10	119.40 (14)
O1—V1—O4	176.32 (5)	C6—C9—H9A	109.5
O3—V1—O4	83.48 (4)	C6—C9—H9B	109.5
O2—V1—O4	83.45 (4)	H9A—C9—H9B	109.5
O5—V1—O4	82.80 (4)	C6—C9—H9C	109.5
N1—V1—O4	82.13 (4)	H9A—C9—H9C	109.5
C1—O2—V1	128.18 (9)	H9B—C9—H9C	109.5
C3—O3—V1	129.31 (9)	C8—C10—H10A	109.5
C6—O4—V1	129.46 (9)	C8—C10—H10B	109.5
C8—O5—V1	132.83 (9)	H10A—C10—H10B	109.5
C13—O6—C16	117.11 (12)	C8—C10—H10C	109.5
C11—N1—C15	116.68 (12)	H10A—C10—H10C	109.5
C11—N1—V1	121.24 (10)	H10B—C10—H10C	109.5
C15—N1—V1	121.92 (10)	N1—C11—C12	124.07 (13)
O2—C1—C2	125.53 (13)	N1—C11—H11	118.0
O2—C1—C5	115.67 (13)	C12—C11—H11	118.0
C2—C1—C5	118.80 (14)	C11—C12—C13	118.10 (13)
C1—C2—C3	124.06 (14)	C11—C12—H12	121.0
C1—C2—H2	118.0	C13—C12—H12	121.0
C3—C2—H2	118.0	O6—C13—C12	124.98 (13)
O3—C3—C2	124.77 (13)	O6—C13—C14	116.26 (13)
O3—C3—C4	115.17 (13)	C12—C13—C14	118.76 (13)
C2—C3—C4	120.05 (13)	C15—C14—C13	118.85 (13)
C3—C4—H4A	109.5	C15—C14—H14	120.6
C3—C4—H4B	109.5	C13—C14—H14	120.6
H4A—C4—H4B	109.5	N1—C15—C14	123.52 (13)
C3—C4—H4C	109.5	N1—C15—H15	118.2
H4A—C4—H4C	109.5	C14—C15—H15	118.2
H4B—C4—H4C	109.5	O6—C16—H16A	109.5
C1—C5—H5A	109.5	O6—C16—H16B	109.5
C1—C5—H5B	109.5	H16A—C16—H16B	109.5
H5A—C5—H5B	109.5	O6—C16—H16C	109.5
C1—C5—H5C	109.5	H16A—C16—H16C	109.5
H5A—C5—H5C	109.5	H16B—C16—H16C	109.5
V1—O2—C1—C2	2.0 (2)	C6—C7—C8—O5	3.7 (3)
V1—O2—C1—C5	−177.67 (11)	C6—C7—C8—C10	−175.99 (16)
O2—C1—C2—C3	−1.8 (3)	C15—N1—C11—C12	−0.6 (2)
C5—C1—C2—C3	177.87 (15)	V1—N1—C11—C12	174.86 (11)
V1—O3—C3—C2	2.2 (2)	N1—C11—C12—C13	−0.9 (2)
V1—O3—C3—C4	−177.27 (10)	C16—O6—C13—C12	−2.3 (2)
C1—C2—C3—O3	−0.4 (2)	C16—O6—C13—C14	177.13 (14)
C1—C2—C3—C4	179.04 (14)	C11—C12—C13—O6	−179.03 (14)
V1—O4—C6—C7	−2.3 (2)	C11—C12—C13—C14	1.6 (2)
V1—O4—C6—C9	179.17 (9)	O6—C13—C14—C15	179.74 (13)
O4—C6—C7—C8	−6.1 (3)	C12—C13—C14—C15	−0.8 (2)
C9—C6—C7—C8	172.47 (15)	C11—N1—C15—C14	1.4 (2)
V1—O5—C8—C7	8.0 (2)	V1—N1—C15—C14	−173.97 (11)
V1—O5—C8—C10	−172.33 (11)	C13—C14—C15—N1	−0.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1^i	0.95	2.57	3.488 (2)	163
C12—H12···O2^ii	0.95	2.37	3.2567 (18)	156
C14—H14···O4^iii	0.95	2.57	3.2462 (18)	129

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z+1.