Methyl 5-[N-(2-hydr­oxyethyl)­carbamo­yl]-2,6-dimethyl-4-(3-nitrophen­yl)-1,4-dihydropyridine-3-carboxylate

The title compound, C₁₈H₂₁N₃O₆, is a nefidipine analog. The crystal packing is stabilized by inter­molecular N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.038
• wR factor = 0.102
• Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.85 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.52 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.37 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................      10.00 Perc.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C6
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      13.00 Deg.
              C16  -N2   -C16'    1.555   1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.86
           From the CIF: _reflns_number_total               2244
           Count of symmetry unique reflns         2246
           Completeness (_total/calc)             99.91%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT792_ALERT_1_G Check the Absolute Configuration of C3     = ...          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: CrystalStructure.

Methyl 5-(2-hydr­oxyethyl­carbamo­yl)-2,6-dimethyl- 4-(3-nitrophen­yl)-1,4-dihydropyridine-3-carboxylate

Crystal data

C18H21N3O6	Dx = 1.407 Mg m^−3
Mr = 375.38	Melting point = 473–474 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71070 Å
a = 14.1028 (15) Å	Cell parameters from 5692 reflections
b = 14.4948 (16) Å	θ = 2.0–27.9°
c = 8.6701 (10) Å	µ = 0.11 mm^−1
V = 1772.3 (3) Å^3	T = 113 K
Z = 4	Block, yellow
F(000) = 792	0.26 × 0.20 × 0.16 mm

Data collection

Rigaku Saturn diffractometer	2244 independent reflections
Radiation source: rotating anode	2066 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.039
Detector resolution: 7.31 pixels mm^-1	θmax = 27.9°, θmin = 2.0°
ω scans	h = −18→18
Absorption correction: multi-scan Jacobson (1998)	k = −16→19
Tmin = 0.970, Tmax = 0.983	l = −11→11
15964 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ^2(Fo^2) + (0.0731P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.102	(Δ/σ)max = 0.002
S = 1.06	Δρmax = 0.28 e Å^−3
2244 reflections	Δρmin = −0.21 e Å^−3
279 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
34 restraints	Extinction coefficient: 0.034 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: 0
Secondary atom site location: difference Fourier map

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. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.41255 (10)	0.19434 (11)	0.8037 (2)	0.0241 (4)
O2	0.53243 (10)	0.10226 (11)	0.8742 (2)	0.0248 (4)
O3	0.58962 (11)	0.51173 (10)	0.4121 (2)	0.0211 (3)
O5	0.21330 (12)	0.39955 (14)	0.3888 (3)	0.0407 (5)
O6	0.19939 (13)	0.31158 (17)	0.1897 (3)	0.0445 (6)
N1	0.72163 (13)	0.29199 (13)	0.6754 (2)	0.0191 (4)
H1	0.7811 (19)	0.2826 (18)	0.697 (3)	0.023*
N2	0.49400 (14)	0.52288 (13)	0.6202 (2)	0.0232 (4)
H2	0.4790 (19)	0.503 (2)	0.712 (4)	0.028*
N3	0.24354 (14)	0.33973 (15)	0.3014 (3)	0.0286 (5)
C1	0.66328 (15)	0.22799 (14)	0.7421 (3)	0.0177 (4)
C2	0.56740 (14)	0.24015 (14)	0.7363 (2)	0.0164 (4)
C3	0.52234 (14)	0.32048 (14)	0.6515 (2)	0.0158 (4)
H3	0.4760	0.3508	0.7226	0.019*
C4	0.59622 (14)	0.39221 (14)	0.6042 (3)	0.0169 (4)
C5	0.68985 (15)	0.37503 (15)	0.6137 (3)	0.0182 (4)
C6	0.71639 (15)	0.14949 (16)	0.8156 (3)	0.0215 (5)
H6A	0.7847	0.1589	0.8021	0.026*
H6B	0.6977	0.0913	0.7667	0.026*
H6C	0.7014	0.1471	0.9259	0.026*
C7	0.49785 (14)	0.17853 (15)	0.8062 (3)	0.0179 (4)
C8	0.46328 (16)	0.03724 (16)	0.9323 (3)	0.0279 (5)
H8A	0.4961	−0.0152	0.9797	0.034*
H8B	0.4237	0.0152	0.8469	0.034*
H8C	0.4232	0.0676	1.0094	0.034*
C9	0.46891 (15)	0.28922 (15)	0.5072 (3)	0.0176 (4)
C10	0.38224 (15)	0.32853 (15)	0.4697 (3)	0.0196 (4)
H10	0.3546	0.3744	0.5337	0.024*
C11	0.33668 (15)	0.29919 (17)	0.3361 (3)	0.0220 (5)
C12	0.37305 (16)	0.23303 (18)	0.2384 (3)	0.0284 (5)
H12	0.3401	0.2148	0.1478	0.034*
C13	0.45923 (18)	0.19441 (17)	0.2774 (3)	0.0296 (6)
H13	0.4864	0.1485	0.2129	0.035*
C14	0.50657 (16)	0.22190 (16)	0.4100 (3)	0.0234 (5)
H14	0.5657	0.1944	0.4350	0.028*
C15	0.56089 (15)	0.48035 (14)	0.5377 (3)	0.0175 (4)
C18	0.76857 (15)	0.43877 (16)	0.5673 (3)	0.0239 (5)
H18A	0.8297	0.4088	0.5863	0.036*	0.50
H18B	0.7647	0.4957	0.6280	0.036*	0.50
H18C	0.7628	0.4535	0.4574	0.036*	0.50
H18D	0.7417	0.4966	0.5282	0.036*	0.50
H18E	0.8068	0.4096	0.4865	0.036*	0.50
H18F	0.8087	0.4518	0.6570	0.036*	0.50
O4	0.28926 (15)	0.5605 (3)	0.6714 (4)	0.0444 (10)	0.886 (9)
H4A	0.3268	0.5401	0.7385	0.053*	0.886 (9)
C16	0.4424 (2)	0.6052 (2)	0.5703 (6)	0.0290 (12)	0.886 (9)
H16A	0.4717	0.6288	0.4743	0.035*	0.886 (9)
H16B	0.4493	0.6536	0.6502	0.035*	0.886 (9)
C17	0.3408 (2)	0.5896 (3)	0.5422 (4)	0.0317 (8)	0.886 (9)
H17A	0.3124	0.6476	0.5034	0.038*	0.886 (9)
H17B	0.3340	0.5426	0.4601	0.038*	0.886 (9)
O4'	0.3123 (18)	0.614 (2)	0.735 (3)	0.053 (7)	0.114 (9)
H4'A	0.3444	0.5775	0.7887	0.064*	0.114 (9)
C16'	0.4586 (14)	0.6165 (11)	0.591 (4)	0.023 (5)	0.114 (9)
H16C	0.4851	0.6393	0.4921	0.027*	0.114 (9)
H16D	0.4805	0.6581	0.6740	0.027*	0.114 (9)
C17'	0.3511 (14)	0.619 (2)	0.583 (3)	0.045 (5)	0.114 (9)
H17C	0.3302	0.6766	0.5319	0.054*	0.114 (9)
H17D	0.3279	0.5662	0.5210	0.054*	0.114 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0140 (7)	0.0252 (8)	0.0332 (9)	−0.0013 (6)	−0.0005 (7)	0.0061 (7)
O2	0.0183 (7)	0.0172 (8)	0.0389 (10)	−0.0022 (6)	−0.0007 (7)	0.0098 (7)
O3	0.0235 (7)	0.0223 (8)	0.0173 (7)	0.0003 (6)	0.0006 (6)	0.0032 (7)
O5	0.0239 (8)	0.0368 (11)	0.0616 (14)	0.0111 (8)	−0.0143 (9)	−0.0038 (10)
O6	0.0273 (10)	0.0744 (16)	0.0319 (10)	0.0032 (9)	−0.0162 (9)	0.0023 (10)
N1	0.0125 (8)	0.0191 (10)	0.0257 (10)	0.0006 (7)	−0.0029 (8)	0.0045 (8)
N2	0.0297 (10)	0.0192 (10)	0.0209 (10)	0.0074 (8)	0.0059 (9)	0.0049 (8)
N3	0.0202 (9)	0.0328 (11)	0.0329 (11)	0.0001 (8)	−0.0052 (9)	0.0110 (10)
C1	0.0188 (10)	0.0163 (10)	0.0179 (9)	0.0005 (8)	−0.0026 (9)	−0.0011 (8)
C2	0.0168 (9)	0.0155 (10)	0.0170 (9)	0.0005 (8)	−0.0013 (8)	−0.0009 (8)
C3	0.0140 (9)	0.0143 (10)	0.0190 (11)	0.0011 (7)	−0.0004 (8)	0.0012 (8)
C4	0.0168 (9)	0.0168 (10)	0.0170 (9)	−0.0008 (8)	−0.0013 (8)	0.0007 (8)
C5	0.0181 (9)	0.0180 (10)	0.0185 (10)	0.0002 (8)	0.0001 (8)	0.0005 (9)
C6	0.0182 (10)	0.0194 (11)	0.0270 (12)	0.0028 (8)	−0.0037 (9)	0.0040 (9)
C7	0.0176 (10)	0.0158 (10)	0.0203 (10)	−0.0011 (8)	−0.0024 (9)	−0.0001 (8)
C8	0.0273 (12)	0.0197 (11)	0.0368 (13)	−0.0076 (9)	−0.0016 (11)	0.0071 (10)
C9	0.0152 (10)	0.0177 (10)	0.0198 (10)	−0.0023 (8)	0.0001 (8)	0.0027 (8)
C10	0.0173 (10)	0.0169 (10)	0.0246 (11)	−0.0004 (8)	−0.0009 (8)	0.0044 (9)
C11	0.0160 (10)	0.0261 (12)	0.0239 (11)	−0.0015 (8)	−0.0048 (9)	0.0078 (9)
C12	0.0260 (12)	0.0360 (14)	0.0231 (11)	−0.0057 (10)	−0.0063 (10)	−0.0016 (11)
C13	0.0290 (12)	0.0314 (13)	0.0283 (13)	0.0035 (10)	−0.0052 (10)	−0.0088 (11)
C14	0.0186 (10)	0.0258 (12)	0.0258 (11)	0.0022 (9)	−0.0023 (10)	−0.0031 (10)
C15	0.0161 (9)	0.0166 (9)	0.0199 (10)	−0.0034 (8)	−0.0018 (8)	−0.0011 (9)
C18	0.0196 (10)	0.0224 (11)	0.0297 (12)	−0.0045 (9)	−0.0012 (9)	0.0048 (10)
O4	0.0237 (11)	0.062 (2)	0.0480 (17)	−0.0023 (12)	−0.0012 (11)	0.0304 (16)
C16	0.0305 (16)	0.0165 (14)	0.040 (3)	0.0078 (13)	0.0093 (19)	0.0112 (17)
C17	0.0408 (17)	0.0236 (16)	0.0308 (16)	0.0074 (13)	−0.0039 (13)	0.0019 (14)
O4'	0.048 (11)	0.072 (14)	0.039 (11)	0.027 (11)	0.012 (9)	0.026 (10)
C16'	0.022 (8)	0.024 (9)	0.021 (8)	0.003 (7)	−0.009 (8)	−0.016 (7)
C17'	0.048 (8)	0.038 (8)	0.050 (8)	0.008 (7)	0.002 (7)	0.007 (7)

Geometric parameters (Å, º)

O1—C7	1.225 (2)	C9—C10	1.387 (3)
O2—C7	1.344 (3)	C9—C14	1.395 (3)
O2—C8	1.447 (3)	C10—C11	1.391 (3)
O3—C15	1.248 (3)	C10—H10	0.9500
O5—N3	1.228 (3)	C11—C12	1.379 (4)
O6—N3	1.221 (3)	C12—C13	1.380 (3)
N1—C1	1.368 (3)	C12—H12	0.9500
N1—C5	1.391 (3)	C13—C14	1.387 (3)
N1—H1	0.87 (3)	C13—H13	0.9500
N2—C15	1.335 (3)	C14—H14	0.9500
N2—C16	1.464 (3)	C18—H18A	0.9800
N2—C16'	1.468 (11)	C18—H18B	0.9800
N2—H2	0.87 (3)	C18—H18C	0.9800
N3—C11	1.470 (3)	C18—H18D	0.9800
C1—C2	1.365 (3)	C18—H18E	0.9800
C1—C6	1.504 (3)	C18—H18F	0.9800
C2—C7	1.459 (3)	O4—C17	1.400 (4)
C2—C3	1.517 (3)	O4—H4A	0.8400
C3—C4	1.528 (3)	C16—C17	1.471 (5)
C3—C9	1.529 (3)	C16—H16A	0.9900
C3—H3	1.0000	C16—H16B	0.9900
C4—C5	1.346 (3)	C17—H17A	0.9900
C4—C15	1.488 (3)	C17—H17B	0.9900
C5—C18	1.499 (3)	O4'—C17'	1.432 (11)
C6—H6A	0.9800	O4'—H4'A	0.8400
C6—H6B	0.9800	C16'—C17'	1.518 (10)
C6—H6C	0.9800	C16'—H16C	0.9900
C8—H8A	0.9800	C16'—H16D	0.9900
C8—H8B	0.9800	C17'—H17C	0.9900
C8—H8C	0.9800	C17'—H17D	0.9900
C7—O2—C8	116.35 (17)	C13—C12—H12	121.4
C1—N1—C5	123.73 (18)	C12—C13—C14	120.7 (2)
C1—N1—H1	112.6 (18)	C12—C13—H13	119.7
C5—N1—H1	121.8 (18)	C14—C13—H13	119.7
C15—N2—C16	124.7 (2)	C13—C14—C9	121.2 (2)
C15—N2—C16'	125.0 (11)	C13—C14—H14	119.4
C16—N2—C16'	13.0 (14)	C9—C14—H14	119.4
C15—N2—H2	120.6 (19)	O3—C15—N2	121.9 (2)
C16—N2—H2	114.7 (19)	O3—C15—C4	122.9 (2)
C16'—N2—H2	112 (2)	N2—C15—C4	115.19 (19)
O6—N3—O5	123.2 (2)	C5—C18—H18A	109.5
O6—N3—C11	119.0 (2)	C5—C18—H18B	109.5
O5—N3—C11	117.8 (2)	H18A—C18—H18B	109.5
C2—C1—N1	119.53 (19)	C5—C18—H18C	109.5
C2—C1—C6	127.4 (2)	H18A—C18—H18C	109.5
N1—C1—C6	113.11 (18)	H18B—C18—H18C	109.5
C1—C2—C7	124.89 (19)	C5—C18—H18D	109.5
C1—C2—C3	122.16 (18)	H18A—C18—H18D	141.1
C7—C2—C3	112.94 (17)	H18B—C18—H18D	56.3
C2—C3—C4	111.51 (16)	H18C—C18—H18D	56.3
C2—C3—C9	112.06 (17)	C5—C18—H18E	109.5
C4—C3—C9	108.56 (16)	H18A—C18—H18E	56.3
C2—C3—H3	108.2	H18B—C18—H18E	141.1
C4—C3—H3	108.2	H18C—C18—H18E	56.3
C9—C3—H3	108.2	H18D—C18—H18E	109.5
C5—C4—C15	120.73 (19)	C5—C18—H18F	109.5
C5—C4—C3	121.77 (19)	H18A—C18—H18F	56.3
C15—C4—C3	117.39 (16)	H18B—C18—H18F	56.3
C4—C5—N1	120.0 (2)	H18C—C18—H18F	141.1
C4—C5—C18	126.6 (2)	H18D—C18—H18F	109.5
N1—C5—C18	113.43 (18)	H18E—C18—H18F	109.5
C1—C6—H6A	109.5	C17—O4—H4A	109.5
C1—C6—H6B	109.5	N2—C16—C17	114.1 (3)
H6A—C6—H6B	109.5	N2—C16—H16A	108.7
C1—C6—H6C	109.5	C17—C16—H16A	108.7
H6A—C6—H6C	109.5	N2—C16—H16B	108.7
H6B—C6—H6C	109.5	C17—C16—H16B	108.7
O1—C7—O2	121.20 (19)	H16A—C16—H16B	107.6
O1—C7—C2	122.6 (2)	O4—C17—C16	114.8 (3)
O2—C7—C2	116.22 (18)	O4—C17—H17A	108.6
O2—C8—H8A	109.5	C16—C17—H17A	108.6
O2—C8—H8B	109.5	O4—C17—H17B	108.6
H8A—C8—H8B	109.5	C16—C17—H17B	108.6
O2—C8—H8C	109.5	H17A—C17—H17B	107.5
H8A—C8—H8C	109.5	C17'—O4'—H4'A	109.5
H8B—C8—H8C	109.5	N2—C16'—C17'	111.6 (11)
C10—C9—C14	118.8 (2)	N2—C16'—H16C	109.3
C10—C9—C3	120.3 (2)	C17'—C16'—H16C	109.3
C14—C9—C3	120.95 (19)	N2—C16'—H16D	109.3
C9—C10—C11	118.5 (2)	C17'—C16'—H16D	109.3
C9—C10—H10	120.8	H16C—C16'—H16D	108.0
C11—C10—H10	120.8	O4'—C17'—C16'	109.8 (11)
C12—C11—C10	123.5 (2)	O4'—C17'—H17C	109.7
C12—C11—N3	119.0 (2)	C16'—C17'—H17C	109.7
C10—C11—N3	117.5 (2)	O4'—C17'—H17D	109.7
C11—C12—C13	117.3 (2)	C16'—C17'—H17D	109.7
C11—C12—H12	121.4	H17C—C17'—H17D	108.2
C5—N1—C1—C2	6.7 (3)	C4—C3—C9—C14	82.3 (2)
C5—N1—C1—C6	−173.4 (2)	C14—C9—C10—C11	−0.2 (3)
N1—C1—C2—C7	−178.3 (2)	C3—C9—C10—C11	178.97 (19)
C6—C1—C2—C7	1.8 (4)	C9—C10—C11—C12	−0.1 (3)
N1—C1—C2—C3	2.9 (3)	C9—C10—C11—N3	178.1 (2)
C6—C1—C2—C3	−177.0 (2)	O6—N3—C11—C12	2.4 (3)
C1—C2—C3—C4	−11.0 (3)	O5—N3—C11—C12	−178.9 (2)
C7—C2—C3—C4	170.04 (18)	O6—N3—C11—C10	−175.9 (2)
C1—C2—C3—C9	110.9 (2)	O5—N3—C11—C10	2.8 (3)
C7—C2—C3—C9	−68.0 (2)	C10—C11—C12—C13	0.2 (4)
C2—C3—C4—C5	11.2 (3)	N3—C11—C12—C13	−177.9 (2)
C9—C3—C4—C5	−112.7 (2)	C11—C12—C13—C14	−0.1 (4)
C2—C3—C4—C15	−172.45 (18)	C12—C13—C14—C9	−0.2 (4)
C9—C3—C4—C15	63.6 (2)	C10—C9—C14—C13	0.3 (3)
C15—C4—C5—N1	−179.6 (2)	C3—C9—C14—C13	−178.8 (2)
C3—C4—C5—N1	−3.4 (3)	C16—N2—C15—O3	4.7 (4)
C15—C4—C5—C18	2.2 (4)	C16'—N2—C15—O3	−11.2 (17)
C3—C4—C5—C18	178.4 (2)	C16—N2—C15—C4	−173.7 (3)
C1—N1—C5—C4	−6.4 (3)	C16'—N2—C15—C4	170.4 (17)
C1—N1—C5—C18	172.0 (2)	C5—C4—C15—O3	48.9 (3)
C8—O2—C7—O1	4.8 (3)	C3—C4—C15—O3	−127.5 (2)
C8—O2—C7—C2	−175.0 (2)	C5—C4—C15—N2	−132.8 (2)
C1—C2—C7—O1	176.8 (2)	C3—C4—C15—N2	50.9 (3)
C3—C2—C7—O1	−4.3 (3)	C15—N2—C16—C17	113.3 (4)
C1—C2—C7—O2	−3.4 (3)	C16'—N2—C16—C17	−151 (5)
C3—C2—C7—O2	175.53 (19)	N2—C16—C17—O4	61.5 (5)
C2—C3—C9—C10	139.5 (2)	C15—N2—C16'—C17'	129.2 (14)
C4—C3—C9—C10	−96.9 (2)	C16—N2—C16'—C17'	36 (4)
C2—C3—C9—C14	−41.3 (3)	N2—C16'—C17'—O4'	77 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3^i	0.84	2.05	2.892 (3)	176
O4′—H4′A···O3^i	0.84	1.92	2.76 (2)	176
N1—H1···O1^ii	0.87 (3)	2.10 (3)	2.920 (2)	157 (2)
N2—H2···O3^i	0.87 (3)	2.00 (3)	2.836 (3)	161 (3)

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