Fe^III in a high-spin state in bis­(5-bromo­sali­cyl­alde­hyde 4-ethyl­thio­semicarbazonato-κ³O,N¹,S)ferrate(III) nitrate monohydrate, the first example of such a cationic Fe^III com­plex unit

The synthesis and crystal structure (100 K) of the title com­pound, [Fe(C₁₀H₁₁BrN₃OS)₂]NO₃·H₂O, is reported. The asymmetric unit consists of an octa­hedral [Fe^III(HL)₂]⁺ cation, where HL⁻ is H-5-Br-thsa-Et or 5-bromo­sali­cyl­alde­hyde 4-ethyl­thio­semicarbazonate(1−) {systematic name: 4-bromo-2-[(4-ethyl­thio­semi­carbazido­idene)meth­yl]­phenolate}, a nitrate anion and a noncoordinated water mol­ecule. Each HL⁻ ligand binds via the thione S, the imine N and the phenolate O atom, resulting in an Fe^IIIS₂N₂O₂ chromophore. The ligands are orientated in two perpendicular planes, with the O and S atoms in cis and the N atoms in trans positions. This [Fe(HL)₂](anion)·H₂O com­pound contains the first known cationic Fe^III entity containing two sali­cyl­alde­hyde thio­semi­car­ba­zone derivatives. The Fe^III ion is in the high-spin state at 100 K. In addition, a com­parative IR spectroscopic study of the free ligand and the ferric com­plex is presented, demonstrating that such an analysis provides a quick identification of the degree of deprotonation and the coordination mode of the ligand in this class of metal com­pounds. The variable-tem­per­ature magnetic susceptibility measurements (5–320 K) are consistent with the presence of a high-spin Fe^III ion with a zero-field splitting D = 0.439 (1) cm⁻¹.

Computing details

Data collection: CrystalClear-SM Expert (Rigaku, 2013); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bis[4-bromo-2-({[(ethylcarbamothioyl)amino]imino}methyl)phenolato-κ³O,N¹,S]ferrate(III) nitrate monohydrate

Crystal data

[Fe(C10H11BrN3OS)2]NO3·H2O[+solvent]	Dx = 1.736 Mg m^−3
Mr = 738.25	Mo Kα radiation, λ = 0.71075 Å
Orthorhombic, Pnna	Cell parameters from 13504 reflections
a = 12.3595 (3) Å	θ = 2.6–27.5°
b = 23.2686 (6) Å	µ = 3.56 mm^−1
c = 19.6406 (6) Å	T = 100 K
V = 5648.4 (3) Å^3	Lath, dark green
Z = 8	0.19 × 0.01 × 0.01 mm
F(000) = 2952

Data collection

Rigaku FRE+ diffractometer equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector	6477 independent reflections
Radiation source: Rotating Anode, Rigaku FRE+	4297 reflections with I > 2σ(I)
Confocal mirrors, HF Varimax monochromator	Rint = 0.088
Detector resolution: 28.5714 pixels mm^-1	θmax = 27.5°, θmin = 2.1°
profile data from ω–scans	h = −15→16
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021)	k = −30→28
Tmin = 0.740, Tmax = 1.000	l = −25→22
36848 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.0514P)^2 + 12.8609P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
6477 reflections	Δρmax = 0.68 e Å^−3
360 parameters	Δρmin = −0.78 e Å^−3
6 restraints

Special details

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

Refinement. H-atoms bonded to N-atoms were located in the difference map and refined with the riding model. All N—H atom pairs were refined with an equal distance geometric restraint. The solvent water molecule was refined as a rigid body group.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br11	1.13632 (5)	0.95165 (3)	0.48873 (4)	0.0628 (3)
Br21	0.40926 (4)	0.48998 (2)	0.39309 (3)	0.03039 (15)
Fe1	0.73206 (5)	0.71905 (3)	0.57014 (4)	0.02070 (17)
S11	0.74079 (10)	0.63438 (5)	0.64326 (7)	0.0263 (3)
S21	0.68261 (10)	0.79079 (5)	0.65684 (7)	0.0281 (3)
O11	0.7817 (3)	0.77756 (15)	0.50614 (18)	0.0292 (8)
O21	0.7228 (3)	0.66978 (15)	0.49042 (18)	0.0283 (8)
N11	0.8946 (3)	0.72721 (17)	0.6116 (2)	0.0214 (9)
N12	0.9239 (3)	0.69112 (19)	0.6653 (2)	0.0289 (10)
H12	0.983 (3)	0.700 (2)	0.687 (2)	0.035*
N13	0.8917 (3)	0.61777 (19)	0.7379 (2)	0.0296 (10)
H13	0.955 (3)	0.623 (2)	0.757 (3)	0.035*
N21	0.5579 (3)	0.71085 (16)	0.5705 (2)	0.0201 (9)
N22	0.4980 (3)	0.74451 (18)	0.6141 (2)	0.0257 (10)
H22	0.429 (3)	0.738 (2)	0.619 (3)	0.031*
N23	0.4797 (3)	0.81161 (18)	0.6965 (2)	0.0263 (10)
H23	0.411 (3)	0.806 (2)	0.691 (3)	0.032*
C11	0.9498 (4)	0.8108 (2)	0.5479 (3)	0.0256 (11)
C12	0.8607 (4)	0.8145 (2)	0.5051 (3)	0.0244 (11)
C13	0.8551 (4)	0.8600 (2)	0.4577 (3)	0.0290 (12)
H13A	0.794568	0.862823	0.428075	0.035*
C14	0.9363 (4)	0.9000 (2)	0.4539 (3)	0.0347 (13)
H14	0.931037	0.930904	0.422416	0.042*
C15	1.0260 (4)	0.8955 (2)	0.4958 (3)	0.0338 (13)
C16	1.0352 (4)	0.8516 (2)	0.5418 (3)	0.0323 (13)
H16	1.097990	0.848317	0.569491	0.039*
C17	0.9642 (4)	0.7670 (2)	0.5979 (3)	0.0250 (11)
H17	1.029907	0.767082	0.622988	0.030*
C18	0.8578 (4)	0.6481 (2)	0.6849 (3)	0.0235 (11)
C19	0.8305 (5)	0.5714 (2)	0.7686 (3)	0.0325 (13)
H19A	0.833418	0.537044	0.738868	0.039*
H19B	0.753821	0.582947	0.773507	0.039*
C21	0.5442 (4)	0.63170 (19)	0.4908 (2)	0.0196 (10)
C22	0.6527 (4)	0.6310 (2)	0.4691 (2)	0.0240 (11)
C23	0.6846 (4)	0.5885 (2)	0.4228 (3)	0.0340 (13)
H23A	0.757209	0.587862	0.407000	0.041*
C24	0.6126 (4)	0.5476 (2)	0.3998 (3)	0.0344 (13)
H24	0.635727	0.519082	0.368365	0.041*
C25	0.5073 (4)	0.5480 (2)	0.4224 (3)	0.0247 (11)
C26	0.4721 (4)	0.5895 (2)	0.4658 (3)	0.0237 (11)
H26	0.398377	0.590122	0.479458	0.028*
C27	0.5019 (4)	0.67281 (19)	0.5378 (2)	0.0218 (11)
H27	0.426046	0.672161	0.545748	0.026*
C28	0.5462 (4)	0.7824 (2)	0.6566 (2)	0.0227 (11)
C29	0.5135 (4)	0.8538 (2)	0.7462 (3)	0.0332 (13)
H29A	0.585645	0.842911	0.764023	0.040*
H29B	0.462069	0.853351	0.784844	0.040*
C110	0.8767 (6)	0.5569 (3)	0.8375 (4)	0.062 (2)
H11A	0.952479	0.545279	0.832449	0.092*
H11B	0.835241	0.525371	0.857747	0.092*
H11C	0.872465	0.590771	0.867077	0.092*
C210	0.5192 (6)	0.9129 (3)	0.7180 (3)	0.0533 (18)
H21A	0.569115	0.913513	0.679198	0.080*
H21B	0.545244	0.939345	0.753204	0.080*
H21C	0.447095	0.924889	0.702894	0.080*
O101	0.7818 (3)	0.7444 (2)	0.3686 (2)	0.0540 (12)
H10A	0.751602	0.725563	0.336775	0.081*
H10B	0.749073	0.733786	0.404481	0.081*
O201	1.2660 (4)	0.6526 (2)	0.7620 (3)	0.0714 (15)
O202	1.1333 (4)	0.6918 (3)	0.7100 (3)	0.089 (2)
O203	1.1007 (4)	0.6406 (3)	0.7980 (2)	0.0736 (17)
N201	1.1666 (4)	0.6618 (2)	0.7581 (3)	0.0460 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br11	0.0369 (4)	0.0510 (4)	0.1004 (6)	−0.0233 (3)	−0.0197 (4)	0.0426 (4)
Br21	0.0335 (3)	0.0198 (2)	0.0379 (3)	−0.0054 (2)	−0.0136 (3)	−0.0019 (2)
Fe1	0.0152 (3)	0.0184 (4)	0.0284 (4)	−0.0044 (3)	−0.0018 (3)	−0.0002 (3)
S11	0.0205 (6)	0.0234 (7)	0.0348 (7)	−0.0046 (5)	−0.0026 (6)	0.0014 (5)
S21	0.0193 (6)	0.0255 (7)	0.0394 (8)	−0.0027 (5)	−0.0049 (6)	−0.0095 (6)
O11	0.0213 (18)	0.038 (2)	0.028 (2)	−0.0125 (16)	−0.0058 (16)	0.0004 (16)
O21	0.0230 (19)	0.031 (2)	0.030 (2)	−0.0085 (15)	0.0049 (16)	−0.0068 (16)
N11	0.017 (2)	0.022 (2)	0.025 (2)	−0.0014 (16)	0.0023 (18)	0.0014 (17)
N12	0.022 (2)	0.030 (2)	0.035 (3)	−0.0082 (19)	−0.008 (2)	0.0061 (19)
N13	0.024 (2)	0.028 (2)	0.036 (3)	−0.0020 (19)	−0.004 (2)	0.006 (2)
N21	0.018 (2)	0.017 (2)	0.026 (2)	0.0008 (16)	−0.0008 (18)	0.0010 (16)
N22	0.018 (2)	0.026 (2)	0.033 (3)	−0.0015 (18)	0.002 (2)	−0.0062 (19)
N23	0.018 (2)	0.031 (2)	0.030 (3)	0.0014 (18)	−0.005 (2)	−0.0043 (19)
C11	0.021 (3)	0.021 (3)	0.035 (3)	0.000 (2)	0.003 (2)	0.001 (2)
C12	0.023 (3)	0.024 (3)	0.027 (3)	−0.002 (2)	0.005 (2)	−0.002 (2)
C13	0.027 (3)	0.032 (3)	0.028 (3)	−0.001 (2)	−0.006 (2)	0.003 (2)
C14	0.032 (3)	0.029 (3)	0.043 (3)	0.000 (2)	0.002 (3)	0.009 (2)
C15	0.023 (3)	0.030 (3)	0.048 (4)	−0.004 (2)	0.003 (3)	0.009 (3)
C16	0.024 (3)	0.029 (3)	0.044 (4)	−0.004 (2)	−0.005 (3)	0.008 (2)
C17	0.016 (2)	0.026 (3)	0.032 (3)	−0.004 (2)	0.000 (2)	−0.001 (2)
C18	0.026 (3)	0.019 (3)	0.026 (3)	0.001 (2)	0.004 (2)	0.001 (2)
C19	0.037 (3)	0.022 (3)	0.038 (3)	−0.004 (2)	0.004 (3)	0.004 (2)
C21	0.019 (2)	0.014 (2)	0.025 (3)	−0.0010 (18)	−0.007 (2)	0.0025 (19)
C22	0.028 (3)	0.026 (3)	0.018 (3)	−0.005 (2)	−0.004 (2)	0.000 (2)
C23	0.027 (3)	0.033 (3)	0.041 (3)	−0.006 (2)	0.002 (3)	−0.012 (3)
C24	0.037 (3)	0.028 (3)	0.038 (3)	−0.005 (2)	−0.002 (3)	−0.012 (2)
C25	0.022 (3)	0.021 (3)	0.031 (3)	−0.007 (2)	−0.012 (2)	0.003 (2)
C26	0.015 (2)	0.019 (3)	0.037 (3)	0.0011 (19)	−0.011 (2)	0.004 (2)
C27	0.015 (2)	0.020 (3)	0.031 (3)	−0.0004 (19)	−0.005 (2)	0.005 (2)
C28	0.023 (3)	0.021 (3)	0.024 (3)	0.001 (2)	−0.002 (2)	0.002 (2)
C29	0.027 (3)	0.038 (3)	0.034 (3)	0.000 (2)	−0.006 (3)	−0.010 (2)
C110	0.068 (5)	0.057 (5)	0.059 (5)	−0.025 (4)	−0.006 (4)	0.023 (4)
C210	0.058 (4)	0.046 (4)	0.056 (4)	−0.006 (3)	−0.007 (4)	−0.013 (3)
O101	0.032 (2)	0.093 (4)	0.037 (2)	−0.016 (2)	0.003 (2)	−0.006 (3)
O201	0.029 (3)	0.094 (4)	0.091 (4)	−0.005 (3)	−0.011 (3)	0.008 (3)
O202	0.029 (3)	0.147 (5)	0.091 (4)	−0.023 (3)	−0.014 (3)	0.074 (4)
O203	0.045 (3)	0.124 (5)	0.052 (3)	−0.024 (3)	0.001 (2)	0.032 (3)
N201	0.034 (3)	0.058 (4)	0.046 (3)	−0.014 (3)	−0.010 (3)	0.004 (3)

Geometric parameters (Å, º)

Br11—C15	1.894 (5)	C14—C15	1.385 (8)
Br21—C25	1.903 (5)	C15—C16	1.369 (7)
Fe1—S11	2.4404 (15)	C16—H16	0.9500
Fe1—S21	2.4615 (14)	C17—H17	0.9500
Fe1—O11	1.952 (3)	C19—H19A	0.9900
Fe1—O21	1.944 (3)	C19—H19B	0.9900
Fe1—N11	2.176 (4)	C19—C110	1.506 (8)
Fe1—N21	2.161 (4)	C21—C22	1.407 (7)
S11—C18	1.692 (5)	C21—C26	1.414 (6)
S21—C28	1.698 (5)	C21—C27	1.429 (7)
O11—C12	1.302 (6)	C22—C23	1.399 (7)
O21—C22	1.320 (6)	C23—H23A	0.9500
N11—N12	1.396 (6)	C23—C24	1.381 (7)
N11—C17	1.293 (6)	C24—H24	0.9500
N12—H12	0.87 (3)	C24—C25	1.374 (7)
N12—C18	1.349 (6)	C25—C26	1.360 (7)
N13—H13	0.88 (3)	C26—H26	0.9500
N13—C18	1.325 (6)	C27—H27	0.9500
N13—C19	1.449 (6)	C29—H29A	0.9900
N21—N22	1.376 (5)	C29—H29B	0.9900
N21—C27	1.295 (6)	C29—C210	1.486 (8)
N22—H22	0.87 (3)	C110—H11A	0.9800
N22—C28	1.352 (6)	C110—H11B	0.9800
N23—H23	0.87 (3)	C110—H11C	0.9800
N23—C28	1.322 (6)	C210—H21A	0.9800
N23—C29	1.446 (6)	C210—H21B	0.9800
C11—C12	1.388 (7)	C210—H21C	0.9800
C11—C16	1.424 (7)	O101—H10A	0.8498
C11—C17	1.426 (7)	O101—H10B	0.8487
C12—C13	1.411 (7)	O201—N201	1.249 (6)
C13—H13A	0.9500	O202—N201	1.246 (7)
C13—C14	1.372 (7)	O203—N201	1.232 (6)
C14—H14	0.9500
S11—Fe1—S21	98.70 (5)	C11—C17—H17	117.5
O11—Fe1—S11	158.16 (11)	N12—C18—S11	121.3 (4)
O11—Fe1—S21	92.89 (11)	N13—C18—S11	123.3 (4)
O11—Fe1—N11	83.71 (14)	N13—C18—N12	115.4 (5)
O11—Fe1—N21	112.13 (14)	N13—C19—H19A	109.7
O21—Fe1—S11	90.03 (11)	N13—C19—H19B	109.7
O21—Fe1—S21	160.48 (11)	N13—C19—C110	110.0 (5)
O21—Fe1—O11	84.89 (15)	H19A—C19—H19B	108.2
O21—Fe1—N11	114.03 (15)	C110—C19—H19A	109.7
O21—Fe1—N21	83.82 (14)	C110—C19—H19B	109.7
N11—Fe1—S11	79.00 (11)	C22—C21—C26	119.2 (4)
N11—Fe1—S21	84.89 (11)	C22—C21—C27	123.5 (4)
N21—Fe1—S11	88.32 (11)	C26—C21—C27	117.3 (4)
N21—Fe1—S21	79.05 (11)	O21—C22—C21	121.5 (4)
N21—Fe1—N11	157.80 (15)	O21—C22—C23	120.3 (5)
C18—S11—Fe1	99.81 (17)	C23—C22—C21	118.2 (4)
C28—S21—Fe1	99.60 (17)	C22—C23—H23A	119.4
C12—O11—Fe1	134.9 (3)	C24—C23—C22	121.2 (5)
C22—O21—Fe1	134.2 (3)	C24—C23—H23A	119.4
N12—N11—Fe1	118.0 (3)	C23—C24—H24	120.0
C17—N11—Fe1	126.8 (3)	C25—C24—C23	120.0 (5)
C17—N11—N12	114.6 (4)	C25—C24—H24	120.0
N11—N12—H12	117 (4)	C24—C25—Br21	120.0 (4)
C18—N12—N11	120.4 (4)	C26—C25—Br21	119.3 (4)
C18—N12—H12	123 (4)	C26—C25—C24	120.7 (5)
C18—N13—H13	123 (4)	C21—C26—H26	119.7
C18—N13—C19	123.9 (4)	C25—C26—C21	120.6 (5)
C19—N13—H13	113 (4)	C25—C26—H26	119.7
N22—N21—Fe1	119.2 (3)	N21—C27—C21	125.6 (4)
C27—N21—Fe1	126.3 (3)	N21—C27—H27	117.2
C27—N21—N22	114.2 (4)	C21—C27—H27	117.2
N21—N22—H22	120 (4)	N22—C28—S21	120.9 (4)
C28—N22—N21	121.2 (4)	N23—C28—S21	123.8 (4)
C28—N22—H22	118 (4)	N23—C28—N22	115.3 (4)
C28—N23—H23	118 (4)	N23—C29—H29A	109.0
C28—N23—C29	124.7 (4)	N23—C29—H29B	109.0
C29—N23—H23	117 (4)	N23—C29—C210	112.9 (5)
C12—C11—C16	119.7 (5)	H29A—C29—H29B	107.8
C12—C11—C17	124.1 (5)	C210—C29—H29A	109.0
C16—C11—C17	116.2 (5)	C210—C29—H29B	109.0
O11—C12—C11	123.0 (5)	C19—C110—H11A	109.5
O11—C12—C13	117.9 (5)	C19—C110—H11B	109.5
C11—C12—C13	119.0 (5)	C19—C110—H11C	109.5
C12—C13—H13A	119.7	H11A—C110—H11B	109.5
C14—C13—C12	120.6 (5)	H11A—C110—H11C	109.5
C14—C13—H13A	119.7	H11B—C110—H11C	109.5
C13—C14—H14	120.0	C29—C210—H21A	109.5
C13—C14—C15	120.1 (5)	C29—C210—H21B	109.5
C15—C14—H14	120.0	C29—C210—H21C	109.5
C14—C15—Br11	118.7 (4)	H21A—C210—H21B	109.5
C16—C15—Br11	120.3 (4)	H21A—C210—H21C	109.5
C16—C15—C14	121.1 (5)	H21B—C210—H21C	109.5
C11—C16—H16	120.3	H10A—O101—H10B	104.6
C15—C16—C11	119.4 (5)	O202—N201—O201	117.9 (5)
C15—C16—H16	120.3	O203—N201—O201	122.9 (6)
N11—C17—C11	124.9 (5)	O203—N201—O202	119.2 (5)
N11—C17—H17	117.5
Br11—C15—C16—C11	178.1 (4)	C14—C15—C16—C11	−1.7 (9)
Br21—C25—C26—C21	177.3 (3)	C16—C11—C12—O11	177.5 (5)
Fe1—S11—C18—N12	−9.9 (4)	C16—C11—C12—C13	−1.9 (7)
Fe1—S11—C18—N13	170.6 (4)	C16—C11—C17—N11	178.4 (5)
Fe1—S21—C28—N22	−1.4 (4)	C17—N11—N12—C18	179.7 (4)
Fe1—S21—C28—N23	179.1 (4)	C17—C11—C12—O11	−0.9 (8)
Fe1—O11—C12—C11	16.4 (8)	C17—C11—C12—C13	179.7 (5)
Fe1—O11—C12—C13	−164.2 (4)	C17—C11—C16—C15	−178.7 (5)
Fe1—O21—C22—C21	23.7 (7)	C18—N13—C19—C110	−165.0 (5)
Fe1—O21—C22—C23	−157.4 (4)	C19—N13—C18—S11	−3.1 (7)
Fe1—N11—N12—C18	7.9 (6)	C19—N13—C18—N12	177.3 (5)
Fe1—N11—C17—C11	−5.6 (7)	C21—C22—C23—C24	−1.1 (8)
Fe1—N21—N22—C28	−0.2 (6)	C22—C21—C26—C25	1.3 (7)
Fe1—N21—C27—C21	−5.3 (7)	C22—C21—C27—N21	−6.3 (8)
O11—C12—C13—C14	−179.6 (5)	C22—C23—C24—C25	−0.1 (9)
O21—C22—C23—C24	180.0 (5)	C23—C24—C25—Br21	−177.9 (4)
N11—N12—C18—S11	2.8 (7)	C23—C24—C25—C26	2.0 (8)
N11—N12—C18—N13	−177.6 (4)	C24—C25—C26—C21	−2.6 (7)
N12—N11—C17—C11	−176.5 (5)	C26—C21—C22—O21	179.4 (4)
N21—N22—C28—S21	1.2 (6)	C26—C21—C22—C23	0.5 (7)
N21—N22—C28—N23	−179.2 (4)	C26—C21—C27—N21	173.1 (4)
N22—N21—C27—C21	−178.5 (4)	C27—N21—N22—C28	173.6 (4)
C11—C12—C13—C14	−0.2 (8)	C27—C21—C22—O21	−1.2 (7)
C12—C11—C16—C15	2.8 (8)	C27—C21—C22—C23	179.9 (5)
C12—C11—C17—N11	−3.2 (8)	C27—C21—C26—C25	−178.1 (4)
C12—C13—C14—C15	1.3 (8)	C28—N23—C29—C210	90.3 (6)
C13—C14—C15—Br11	179.8 (4)	C29—N23—C28—S21	−1.2 (7)
C13—C14—C15—C16	−0.4 (9)	C29—N23—C28—N22	179.3 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···O202	0.87 (3)	1.92 (4)	2.733 (6)	155 (5)
N13—H13···O203	0.88 (3)	2.02 (3)	2.890 (6)	176 (5)
N22—H22···O101^i	0.87 (3)	1.85 (3)	2.695 (6)	166 (5)
N23—H23···O201^ii	0.87 (3)	2.23 (4)	2.887 (6)	133 (4)
O101—H10A···O202^i	0.85	1.90	2.692 (6)	155
O101—H10B···O11	0.85	2.28	2.809 (6)	121

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