Crystal structure of (μ-hydrogen di­sulfato)-μ-oxido-bis­[(4,4′-di-tert-butyl-2,2′-bi­pyridine)­oxidovanadium(IV/V)] aceto­nitrile monosolvate

The crystal structure of a dinuclear oxidovanadium(IV/V) complex [V₂O₂(μ-O)(μ-H(SO₄)₂)(4,4′-^tBubpy)₂] aceto­nitrile monosolvate has been determined.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 110 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.043
• wR factor = 0.110
• Data-to-parameter ratio = 22.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT601_ALERT_2_C Unit Cell Contains Solvent Accessible VOIDS of .         91 Ang   3
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.402 Check

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          3 Report
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      46.65 Why ?
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V1       --O1       .        5.7 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V1       --O2       .       24.6 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V1       --N2       .        5.3 s.u.
PLAT300_ALERT_4_G Atom Site Occupancy of H6         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of N3         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C19        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C20        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H19A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H19B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H19C       Constrained at        0.5 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT789_ALERT_4_G Atoms with Negative _atom_site_disorder_group  #          6 Check
PLAT794_ALERT_5_G Tentative Bond Valency for V1        (V)       .       4.83 Info
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          3 Info
PLAT822_ALERT_4_G CIF-embedded .res Contains Negative PART Numbers          1 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         27 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        288 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          3 Note
PLAT954_ALERT_1_G Reported (CIF) and Actual (FCF) Kmax Differ by .          1 Units
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
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  26 ALERT level G = General information/check it is not something unexpected

   1 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
   4 ALERT type 3 Indicator that the structure quality may be low
  14 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011); cell refinement: CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011); data reduction: CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011); program(s) used to solve structure: olex2.solve 1.5 (Bourhis et al., 2015); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009).

(µ-Hydrogen disulfato)-µ-oxido-bis[(4,4'-di-tert-butyl-2,2'-bipyridine)oxidovanadium(IV/V)] acetonitrile monosolvate

Crystal data

[V2(HS2O8)O3(C18H24N2)2]·C2H3N	Dx = 1.362 Mg m^−3
Mr = 920.84	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fddd	Cell parameters from 30626 reflections
a = 13.0134 (2) Å	θ = 1.9–30.6°
b = 34.9495 (5) Å	µ = 0.57 mm^−1
c = 39.4864 (6) Å	T = 110 K
V = 17958.9 (5) Å^3	Block, clear dark brown
Z = 16	0.16 × 0.11 × 0.06 mm
F(000) = 7696

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	6582 independent reflections
Radiation source: Rotating Anode	5675 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.049
profile data from ω–scans	θmax = 30.5°, θmin = 2.1°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	h = −18→18
Tmin = 0.815, Tmax = 1.000	k = −49→50
51528 measured reflections	l = −55→54

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0469P)^2 + 46.648P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.003
6582 reflections	Δρmax = 0.50 e Å^−3
287 parameters	Δρmin = −0.33 e Å^−3
27 restraints

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	Occ. (<1)
V1	0.70713 (2)	0.54069 (2)	0.59096 (2)	0.02335 (8)
S1	0.75306 (3)	0.47690 (2)	0.64590 (2)	0.02120 (10)
O5	0.66572 (10)	0.49435 (3)	0.66352 (3)	0.0235 (2)
O3	0.78535 (10)	0.50242 (4)	0.61695 (3)	0.0255 (3)
O6	0.71873 (10)	0.43950 (3)	0.63066 (3)	0.0258 (3)
O4	0.84010 (10)	0.46966 (4)	0.66746 (3)	0.0299 (3)
O1	0.79258 (12)	0.57322 (4)	0.58859 (3)	0.0369 (3)
O2	0.625000	0.55852 (5)	0.625000	0.0394 (5)
N2	0.75091 (11)	0.51363 (4)	0.54454 (3)	0.0216 (3)
N1	0.60817 (12)	0.56465 (4)	0.55441 (3)	0.0224 (3)
C3	0.48418 (13)	0.59696 (5)	0.50377 (4)	0.0225 (3)
C6	0.69971 (13)	0.52426 (5)	0.51604 (4)	0.0202 (3)
C7	0.72724 (13)	0.51037 (5)	0.48439 (4)	0.0223 (3)
H7	0.688735	0.517593	0.464972	0.027*
C8	0.81169 (13)	0.48568 (5)	0.48092 (4)	0.0252 (3)
C11	0.41640 (14)	0.61383 (5)	0.47598 (5)	0.0260 (3)
C4	0.55602 (13)	0.56814 (4)	0.49641 (4)	0.0210 (3)
H4	0.562535	0.558953	0.473872	0.025*
C5	0.61741 (13)	0.55301 (4)	0.52172 (4)	0.0200 (3)
C2	0.47668 (14)	0.60821 (5)	0.53749 (5)	0.0265 (3)
H2	0.428897	0.627475	0.543821	0.032*
C10	0.83025 (13)	0.48947 (5)	0.54148 (4)	0.0259 (3)
H10	0.865230	0.481514	0.561393	0.031*
C9	0.86340 (14)	0.47561 (5)	0.51049 (5)	0.0283 (4)
H9	0.921500	0.459194	0.509397	0.034*
C1	0.53844 (15)	0.59148 (5)	0.56180 (4)	0.0266 (3)
H1	0.531067	0.599365	0.584695	0.032*
C15	0.84388 (15)	0.47210 (6)	0.44572 (5)	0.0329 (4)
C12	0.48286 (15)	0.62876 (5)	0.44658 (5)	0.0310 (4)
H12A	0.524627	0.607783	0.437528	0.047*
H12B	0.527993	0.649180	0.454815	0.047*
H12C	0.438268	0.638807	0.428664	0.047*
C13	0.34999 (16)	0.64692 (6)	0.48896 (6)	0.0375 (5)
H13A	0.394311	0.666815	0.498583	0.056*
H13B	0.302988	0.637465	0.506451	0.056*
H13C	0.310203	0.657649	0.470150	0.056*
C14	0.34585 (16)	0.58193 (6)	0.46305 (5)	0.0346 (4)
H14A	0.299790	0.573763	0.481303	0.052*
H14B	0.387562	0.560154	0.455598	0.052*
H14C	0.305067	0.591466	0.443967	0.052*
C18	0.93513 (18)	0.44437 (7)	0.44714 (6)	0.0434 (5)
H18A	0.915526	0.421472	0.459928	0.065*
H18B	0.993353	0.456879	0.458329	0.065*
H18C	0.954806	0.437044	0.424081	0.065*
C17	0.87660 (19)	0.50771 (7)	0.42503 (5)	0.0437 (5)
H17A	0.929138	0.521948	0.437572	0.065*
H17B	0.816724	0.524171	0.421258	0.065*
H17C	0.904661	0.499545	0.403158	0.065*
C16	0.75339 (19)	0.45218 (7)	0.42815 (6)	0.0467 (6)
H16A	0.695186	0.469893	0.426686	0.070*
H16B	0.733200	0.429568	0.441237	0.070*
H16C	0.773966	0.444343	0.405306	0.070*
N3	0.6842 (6)	0.5900 (2)	0.3294 (2)	0.102 (2)	0.5
C19	0.5721 (5)	0.64049 (17)	0.36076 (15)	0.0605 (14)	0.5
H19A	0.549690	0.660308	0.344825	0.091*	0.5
H19B	0.611988	0.652277	0.379037	0.091*	0.5
H19C	0.511740	0.627648	0.370330	0.091*	0.5
C20	0.6367 (5)	0.61212 (17)	0.34275 (17)	0.0616 (15)	0.5
H6	0.659 (3)	0.4376 (11)	0.6263 (12)	0.022 (11)*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
V1	0.03845 (17)	0.01764 (13)	0.01395 (13)	−0.00275 (11)	−0.00195 (11)	0.00237 (10)
S1	0.0276 (2)	0.01950 (18)	0.01648 (18)	−0.00117 (15)	−0.00710 (15)	0.00280 (14)
O5	0.0351 (6)	0.0179 (5)	0.0175 (5)	0.0015 (5)	−0.0031 (5)	0.0012 (4)
O3	0.0312 (6)	0.0263 (6)	0.0188 (6)	−0.0014 (5)	−0.0056 (5)	0.0055 (5)
O6	0.0299 (7)	0.0197 (5)	0.0278 (6)	0.0026 (5)	−0.0082 (5)	−0.0035 (5)
O4	0.0337 (7)	0.0335 (7)	0.0225 (6)	−0.0012 (5)	−0.0126 (5)	0.0061 (5)
O1	0.0574 (9)	0.0273 (6)	0.0260 (7)	−0.0137 (6)	−0.0164 (6)	0.0075 (5)
O2	0.0866 (16)	0.0163 (8)	0.0154 (8)	0.000	−0.0162 (9)	0.000
N2	0.0258 (7)	0.0224 (6)	0.0165 (6)	−0.0021 (5)	−0.0045 (5)	0.0027 (5)
N1	0.0361 (8)	0.0169 (6)	0.0142 (6)	−0.0020 (5)	0.0000 (5)	−0.0007 (5)
C3	0.0267 (8)	0.0173 (7)	0.0236 (8)	−0.0009 (6)	−0.0029 (6)	−0.0032 (6)
C6	0.0248 (7)	0.0199 (7)	0.0160 (7)	−0.0009 (6)	−0.0030 (6)	0.0017 (6)
C7	0.0259 (8)	0.0238 (7)	0.0171 (7)	0.0025 (6)	−0.0047 (6)	−0.0001 (6)
C8	0.0259 (8)	0.0288 (8)	0.0207 (8)	0.0024 (7)	−0.0022 (6)	−0.0010 (6)
C11	0.0290 (8)	0.0202 (7)	0.0289 (8)	0.0042 (6)	−0.0069 (7)	−0.0053 (6)
C4	0.0267 (8)	0.0196 (7)	0.0167 (7)	0.0002 (6)	−0.0016 (6)	−0.0022 (6)
C5	0.0280 (8)	0.0163 (6)	0.0157 (7)	−0.0014 (6)	−0.0010 (6)	−0.0007 (5)
C2	0.0331 (9)	0.0202 (7)	0.0260 (8)	0.0017 (6)	0.0018 (7)	−0.0064 (6)
C10	0.0255 (8)	0.0306 (8)	0.0216 (8)	0.0004 (7)	−0.0069 (6)	0.0034 (7)
C9	0.0252 (8)	0.0342 (9)	0.0257 (8)	0.0061 (7)	−0.0041 (7)	0.0014 (7)
C1	0.0418 (10)	0.0195 (7)	0.0185 (7)	−0.0011 (7)	0.0019 (7)	−0.0046 (6)
C15	0.0333 (9)	0.0419 (10)	0.0234 (8)	0.0141 (8)	−0.0034 (7)	−0.0064 (8)
C12	0.0378 (10)	0.0261 (8)	0.0292 (9)	0.0026 (7)	−0.0079 (7)	0.0021 (7)
C13	0.0373 (10)	0.0317 (10)	0.0436 (11)	0.0128 (8)	−0.0062 (9)	−0.0083 (8)
C14	0.0348 (10)	0.0284 (9)	0.0407 (11)	−0.0005 (7)	−0.0120 (8)	−0.0066 (8)
C18	0.0416 (11)	0.0547 (13)	0.0337 (11)	0.0206 (10)	−0.0025 (9)	−0.0081 (10)
C17	0.0523 (13)	0.0544 (13)	0.0243 (9)	0.0141 (11)	0.0077 (9)	0.0033 (9)
C16	0.0444 (12)	0.0551 (14)	0.0404 (12)	0.0158 (10)	−0.0109 (10)	−0.0243 (11)
N3	0.088 (4)	0.100 (4)	0.117 (5)	−0.037 (3)	0.042 (4)	−0.029 (4)
C19	0.073 (3)	0.063 (3)	0.045 (3)	−0.037 (3)	0.003 (3)	−0.007 (2)
C20	0.053 (3)	0.065 (3)	0.067 (3)	−0.022 (3)	0.008 (3)	0.001 (2)

Geometric parameters (Å, º)

V1—O5^i	2.2827 (12)	C10—H10	0.9500
V1—O3	1.9692 (12)	C10—C9	1.385 (3)
V1—O1	1.5932 (14)	C9—H9	0.9500
V1—O2	1.8268 (7)	C1—H1	0.9500
V1—N2	2.1399 (14)	C15—C18	1.534 (3)
V1—N1	2.1077 (14)	C15—C17	1.549 (3)
S1—O5	1.4654 (13)	C15—C16	1.534 (3)
S1—O3	1.5098 (12)	C12—H12A	0.9800
S1—O6	1.5066 (13)	C12—H12B	0.9800
S1—O4	1.4391 (13)	C12—H12C	0.9800
O6—H6	0.80 (4)	C13—H13A	0.9800
N2—C6	1.360 (2)	C13—H13B	0.9800
N2—C10	1.339 (2)	C13—H13C	0.9800
N1—C5	1.359 (2)	C14—H14A	0.9800
N1—C1	1.337 (2)	C14—H14B	0.9800
C3—C11	1.526 (2)	C14—H14C	0.9800
C3—C4	1.405 (2)	C18—H18A	0.9800
C3—C2	1.392 (2)	C18—H18B	0.9800
C6—C7	1.388 (2)	C18—H18C	0.9800
C6—C5	1.486 (2)	C17—H17A	0.9800
C7—H7	0.9500	C17—H17B	0.9800
C7—C8	1.404 (2)	C17—H17C	0.9800
C8—C9	1.393 (2)	C16—H16A	0.9800
C8—C15	1.527 (2)	C16—H16B	0.9800
C11—C12	1.539 (3)	C16—H16C	0.9800
C11—C13	1.532 (2)	N3—C20	1.120 (9)
C11—C14	1.532 (2)	C19—H19A	0.9800
C4—H4	0.9500	C19—H19B	0.9800
C4—C5	1.384 (2)	C19—H19C	0.9800
C2—H2	0.9500	C19—C20	1.482 (8)
C2—C1	1.382 (3)
O3—V1—O5^i	85.44 (5)	N2—C10—H10	118.7
O3—V1—N2	90.49 (5)	N2—C10—C9	122.69 (15)
O3—V1—N1	160.47 (5)	C9—C10—H10	118.7
O1—V1—O5^i	172.18 (6)	C8—C9—H9	119.9
O1—V1—O3	98.89 (7)	C10—C9—C8	120.11 (16)
O1—V1—O2	102.02 (7)	C10—C9—H9	119.9
O1—V1—N2	94.54 (7)	N1—C1—C2	122.68 (16)
O1—V1—N1	95.89 (6)	N1—C1—H1	118.7
O2—V1—O5^i	83.64 (5)	C2—C1—H1	118.7
O2—V1—O3	98.66 (5)	C8—C15—C18	112.05 (16)
O2—V1—N2	159.52 (5)	C8—C15—C17	107.79 (16)
O2—V1—N1	90.62 (5)	C8—C15—C16	110.01 (17)
N2—V1—O5^i	78.84 (5)	C18—C15—C17	108.31 (18)
N1—V1—O5^i	78.52 (5)	C18—C15—C16	108.92 (18)
N1—V1—N2	75.63 (5)	C16—C15—C17	109.72 (18)
O5—S1—O3	109.23 (7)	C11—C12—H12A	109.5
O5—S1—O6	108.70 (8)	C11—C12—H12B	109.5
O6—S1—O3	107.02 (7)	C11—C12—H12C	109.5
O4—S1—O5	113.76 (8)	H12A—C12—H12B	109.5
O4—S1—O3	109.43 (8)	H12A—C12—H12C	109.5
O4—S1—O6	108.49 (8)	H12B—C12—H12C	109.5
S1—O5—V1^i	143.30 (7)	C11—C13—H13A	109.5
S1—O3—V1	130.69 (8)	C11—C13—H13B	109.5
S1—O6—H6	117 (3)	C11—C13—H13C	109.5
V1—O2—V1^i	140.11 (10)	H13A—C13—H13B	109.5
C6—N2—V1	117.24 (11)	H13A—C13—H13C	109.5
C10—N2—V1	124.13 (11)	H13B—C13—H13C	109.5
C10—N2—C6	118.41 (14)	C11—C14—H14A	109.5
C5—N1—V1	118.52 (11)	C11—C14—H14B	109.5
C1—N1—V1	122.95 (11)	C11—C14—H14C	109.5
C1—N1—C5	118.51 (15)	H14A—C14—H14B	109.5
C4—C3—C11	120.86 (15)	H14A—C14—H14C	109.5
C2—C3—C11	122.56 (15)	H14B—C14—H14C	109.5
C2—C3—C4	116.56 (15)	C15—C18—H18A	109.5
N2—C6—C7	121.55 (15)	C15—C18—H18B	109.5
N2—C6—C5	114.41 (14)	C15—C18—H18C	109.5
C7—C6—C5	123.97 (14)	H18A—C18—H18B	109.5
C6—C7—H7	119.8	H18A—C18—H18C	109.5
C6—C7—C8	120.33 (15)	H18B—C18—H18C	109.5
C8—C7—H7	119.8	C15—C17—H17A	109.5
C7—C8—C15	119.64 (15)	C15—C17—H17B	109.5
C9—C8—C7	116.86 (16)	C15—C17—H17C	109.5
C9—C8—C15	123.49 (16)	H17A—C17—H17B	109.5
C3—C11—C12	110.40 (15)	H17A—C17—H17C	109.5
C3—C11—C13	112.15 (15)	H17B—C17—H17C	109.5
C3—C11—C14	107.75 (14)	C15—C16—H16A	109.5
C13—C11—C12	108.28 (16)	C15—C16—H16B	109.5
C14—C11—C12	109.39 (15)	C15—C16—H16C	109.5
C14—C11—C13	108.84 (16)	H16A—C16—H16B	109.5
C3—C4—H4	119.7	H16A—C16—H16C	109.5
C5—C4—C3	120.58 (15)	H16B—C16—H16C	109.5
C5—C4—H4	119.7	H19A—C19—H19B	109.5
N1—C5—C6	114.19 (14)	H19A—C19—H19C	109.5
N1—C5—C4	121.35 (15)	H19B—C19—H19C	109.5
C4—C5—C6	124.43 (14)	C20—C19—H19A	109.5
C3—C2—H2	119.9	C20—C19—H19B	109.5
C1—C2—C3	120.28 (16)	C20—C19—H19C	109.5
C1—C2—H2	119.9	N3—C20—C19	178.4 (7)
V1—N2—C6—C7	175.43 (12)	C7—C6—C5—N1	−175.49 (16)
V1—N2—C6—C5	−1.51 (18)	C7—C6—C5—C4	2.7 (3)
V1—N2—C10—C9	−172.91 (14)	C7—C8—C9—C10	0.7 (3)
V1—N1—C5—C6	−0.61 (18)	C7—C8—C15—C18	−178.11 (18)
V1—N1—C5—C4	−178.82 (12)	C7—C8—C15—C17	62.8 (2)
V1—N1—C1—C2	177.27 (13)	C7—C8—C15—C16	−56.8 (2)
O5^i—V1—O2—V1^i	36.88 (3)	C11—C3—C4—C5	179.87 (15)
O5—S1—O3—V1	−24.59 (12)	C11—C3—C2—C1	178.68 (16)
O3—V1—O2—V1^i	−47.50 (4)	C4—C3—C11—C12	−54.6 (2)
O3—S1—O5—V1^i	14.21 (15)	C4—C3—C11—C13	−175.46 (16)
O6—S1—O5—V1^i	−102.23 (13)	C4—C3—C11—C14	64.8 (2)
O6—S1—O3—V1	92.92 (11)	C4—C3—C2—C1	0.4 (3)
O4—S1—O5—V1^i	136.79 (12)	C5—N1—C1—C2	−1.0 (3)
O4—S1—O3—V1	−149.72 (10)	C5—C6—C7—C8	174.54 (16)
O1—V1—O2—V1^i	−148.59 (5)	C2—C3—C11—C12	127.22 (18)
N2—V1—O2—V1^i	68.14 (17)	C2—C3—C11—C13	6.4 (2)
N2—C6—C7—C8	−2.1 (3)	C2—C3—C11—C14	−113.38 (19)
N2—C6—C5—N1	1.4 (2)	C2—C3—C4—C5	−1.9 (2)
N2—C6—C5—C4	179.52 (15)	C10—N2—C6—C7	0.7 (2)
N2—C10—C9—C8	−2.1 (3)	C10—N2—C6—C5	−176.23 (15)
N1—V1—O2—V1^i	115.25 (4)	C9—C8—C15—C18	3.4 (3)
C3—C4—C5—N1	1.9 (2)	C9—C8—C15—C17	−115.7 (2)
C3—C4—C5—C6	−176.08 (15)	C9—C8—C15—C16	124.7 (2)
C3—C2—C1—N1	1.0 (3)	C1—N1—C5—C6	177.74 (15)
C6—N2—C10—C9	1.4 (3)	C1—N1—C5—C4	−0.5 (2)
C6—C7—C8—C9	1.3 (3)	C15—C8—C9—C10	179.22 (18)
C6—C7—C8—C15	−177.25 (17)

Symmetry code: (i) −x+5/4, y, −z+5/4.

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the N2/C6–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···Cg2^ii	0.98	2.78	3.431 (2)	124

Symmetry code: (ii) −x+1, −y+1, −z+1.