Two tautomers in one crystal: 4(5)-nitro-5(4)-methoxyimidazole

The case of prototropic annular tautomerism in an imidazole derivative has been found. The crystal structure contains a 50:50 mixture of two tautomers: 4-nitro-5-methoxyimidazole and 5-nitro-4-methoxyimidazole. The X-ray experiment actually shows the superposition of these compounds; it appears as if the structure is centrosymmetric and the N—H hydrogen atoms are disordered over two ring N atoms. Owing to the hydrogen-bond pattern, the values of their site occupation factors have to be exactly equal to 1/2. The molecules are connected into a three-dimensional network by means of N—H...N and C—H...O hydrogen bonds.

Computing details

For both compounds, data collection: CrysAlis CCD v.169; cell refinement: CrysAlis CCD v.169; data reduction: CrysAlis RED v.169; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

Figures

(1) 4(5)-nitro-5(4)-methoxy-1H-imidazole

Crystal data

C4H5N3O3	F(000) = 592
Mr = 143.11	Dx = 1.660 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4048 reflections
a = 7.5542 (6) Å	θ = 4–22°
b = 11.3112 (9) Å	µ = 0.14 mm^−1
c = 13.4773 (10) Å	T = 90 K
β = 95.920 (6)°	Prism, colourless
V = 1145.45 (15) Å^3	0.2 × 0.2 × 0.1 mm
Z = 8

Data collection

KUMA KM4CCD four-circle diffractometer	1513 independent reflections
Radiation source: fine-focus sealed tube	1266 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
/w scan	θmax = 29.0°, θmin = 3.3°
Absorption correction: multi-scan SORTAV (Blessing, 1989)	h = −10→7
Tmin = 0.983, Tmax = 0.984	k = −15→15
7556 measured reflections	l = −17→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: difference Fourier map
wR(F^2) = 0.080	All H-atom parameters refined
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0464P)^2 + 0.0996P] where P = (Fo^2 + 2Fc^2)/3
1567 reflections	(Δ/σ)max < 0.001
115 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

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)
N1	0.59381 (11)	0.92865 (7)	0.34804 (6)	0.01395 (19)
H1	0.533 (3)	0.927 (2)	0.2932 (18)	0.017 (6)*	0.50
C2	0.75692 (13)	0.98053 (9)	0.36613 (7)	0.0155 (2)
H2	0.8117 (15)	1.0230 (11)	0.3179 (9)	0.018 (3)*
N3	0.82832 (11)	0.96510 (7)	0.45830 (6)	0.01428 (19)
H3	0.936 (3)	0.988 (2)	0.4810 (19)	0.017 (6)*	0.50
C4	0.70651 (12)	0.89944 (8)	0.50417 (7)	0.0134 (2)
N4	0.73546 (11)	0.86677 (7)	0.60484 (6)	0.01406 (18)
O41	0.62036 (10)	0.80732 (7)	0.64056 (5)	0.02048 (19)
O42	0.87603 (9)	0.89940 (7)	0.65360 (5)	0.01926 (18)
C5	0.56102 (12)	0.87666 (8)	0.43511 (7)	0.0129 (2)
O5	0.41617 (9)	0.81572 (6)	0.45016 (5)	0.01594 (17)
C51	0.28526 (14)	0.80036 (10)	0.36430 (7)	0.0184 (2)
H51A	0.1936 (17)	0.7555 (11)	0.3893 (10)	0.020 (3)*
H51B	0.3403 (18)	0.7604 (11)	0.3098 (10)	0.024 (3)*
H51C	0.2343 (18)	0.8776 (11)	0.3405 (11)	0.026 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0140 (4)	0.0166 (4)	0.0109 (4)	−0.0006 (3)	−0.0006 (3)	0.0007 (3)
C2	0.0164 (5)	0.0173 (5)	0.0125 (5)	−0.0017 (4)	0.0004 (3)	0.0007 (3)
N3	0.0134 (4)	0.0174 (4)	0.0118 (4)	−0.0013 (3)	0.0002 (3)	−0.0003 (3)
C4	0.0131 (4)	0.0157 (4)	0.0111 (4)	0.0001 (3)	0.0005 (3)	0.0000 (3)
N4	0.0126 (4)	0.0167 (4)	0.0126 (4)	0.0007 (3)	0.0000 (3)	−0.0009 (3)
O41	0.0166 (4)	0.0290 (4)	0.0160 (4)	−0.0047 (3)	0.0020 (3)	0.0043 (3)
O42	0.0153 (4)	0.0277 (4)	0.0137 (4)	−0.0030 (3)	−0.0038 (3)	−0.0007 (3)
C5	0.0134 (4)	0.0135 (4)	0.0118 (4)	0.0014 (3)	0.0015 (3)	−0.0009 (3)
O5	0.0128 (3)	0.0222 (4)	0.0124 (3)	−0.0049 (3)	−0.0009 (2)	0.0010 (3)
C51	0.0149 (5)	0.0246 (5)	0.0147 (5)	−0.0056 (4)	−0.0034 (4)	0.0017 (4)

Geometric parameters (Å, º)

N1—C5	1.3580 (12)	C4—N4	1.4014 (12)
N1—C2	1.3638 (13)	N4—O41	1.2354 (10)
N1—H1	0.83 (2)	N4—O42	1.2457 (11)
C2—N3	1.3139 (12)	C5—O5	1.3265 (12)
C2—H2	0.938 (12)	O5—C51	1.4530 (11)
N3—C4	1.3776 (12)	C51—H51A	0.948 (13)
N3—H3	0.87 (2)	C51—H51B	0.991 (13)
C4—C5	1.3891 (13)	C51—H51C	0.995 (13)
C5—N1—C2	105.89 (8)	O41—N4—C4	118.36 (8)
C5—N1—H1	128.6 (17)	O42—N4—C4	118.17 (8)
C2—N1—H1	125.4 (17)	O5—C5—N1	125.74 (8)
N3—C2—N1	112.77 (9)	O5—C5—C4	127.02 (8)
N3—C2—H2	123.7 (8)	N1—C5—C4	107.25 (8)
N1—C2—H2	123.5 (7)	C5—O5—C51	116.40 (7)
C2—N3—C4	105.53 (8)	O5—C51—H51A	104.1 (8)
C2—N3—H3	124.5 (17)	O5—C51—H51B	110.0 (8)
C4—N3—H3	129.7 (17)	H51A—C51—H51B	113.4 (11)
N3—C4—C5	108.56 (8)	O5—C51—H51C	111.2 (8)
N3—C4—N4	122.13 (8)	H51A—C51—H51C	108.2 (10)
C5—C4—N4	129.31 (9)	H51B—C51—H51C	109.9 (11)
O41—N4—O42	123.47 (8)
C5—N1—C2—N3	−0.20 (11)	C2—N1—C5—O5	−179.69 (9)
N1—C2—N3—C4	0.01 (11)	C2—N1—C5—C4	0.31 (10)
C2—N3—C4—C5	0.19 (11)	N3—C4—C5—O5	179.68 (9)
C2—N3—C4—N4	−178.97 (9)	N4—C4—C5—O5	−1.24 (17)
N3—C4—N4—O41	−179.65 (8)	N3—C4—C5—N1	−0.31 (11)
C5—C4—N4—O41	1.39 (15)	N4—C4—C5—N1	178.76 (9)
N3—C4—N4—O42	0.44 (13)	N1—C5—O5—C51	2.38 (14)
C5—C4—N4—O42	−178.53 (9)	C4—C5—O5—C51	−177.62 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N1^i	0.83 (2)	2.04 (3)	2.8670 (16)	174 (2)
C2—H2···O42^ii	0.938 (12)	2.477 (12)	3.3749 (12)	160.4 (10)
C2—H2···O42^iii	0.938 (12)	2.509 (12)	3.1235 (13)	123.3 (9)
N3—H3···N3^iii	0.87 (2)	1.96 (2)	2.8307 (17)	176 (2)
C51—H51A···O41^iv	0.948 (13)	2.469 (13)	3.2918 (13)	145.2 (11)
C51—H51A···O5^iv	0.948 (13)	2.528 (13)	3.3283 (13)	142.3 (11)
C51—H51C···O42^v	0.995 (13)	2.660 (13)	3.6077 (14)	159.3 (11)

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

(2) 4(5)-nitro-5(4)-methoxy-1H-imidazole

Crystal data

C4H5N3O3	F(000) = 592
Mr = 143.11	Dx = 1.660 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 4048 reflections
a = 7.5542 (6) Å	θ = 4–22°
b = 11.3112 (9) Å	µ = 0.14 mm^−1
c = 13.4773 (10) Å	T = 90 K
β = 95.920 (6)°	Prism, colourless
V = 1145.45 (15) Å^3	0.2 × 0.2 × 0.1 mm
Z = 8

Data collection

KUMA KM4CCD four-circle diffractometer	2380 independent reflections
Radiation source: fine-focus sealed tube	1876 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
/w scan	θmax = 29.9°, θmin = 3.0°
Absorption correction: multi-scan SORTAV (Blessing, 1989)	h = −10→7
Tmin = 0.983, Tmax = 0.984	k = −15→15
7556 measured reflections	l = −17→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full with fixed elements per cycle	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.074	w = 1/[σ^2(Fo^2) + (0.043P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.120
2380 reflections	Δρmax = 0.22 e Å^−3
193 parameters	Δρmin = −0.26 e Å^−3
2 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 1 (2)

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
N1A	0.66219 (18)	0.57146 (11)	0.62985 (9)	0.0131 (3)
H1A	0.599 (2)	0.5720 (16)	0.5774 (14)	0.016*
C2A	0.8234 (2)	0.52011 (13)	0.64684 (11)	0.0161 (3)
H2A	0.887 (2)	0.4872 (16)	0.5987 (14)	0.019*
N3A	0.89693 (17)	0.53538 (11)	0.74040 (9)	0.0136 (3)
C4A	0.7737 (2)	0.59970 (13)	0.78532 (11)	0.0150 (3)
N4A	0.80112 (18)	0.63272 (11)	0.88544 (10)	0.0166 (3)
O41A	0.94363 (15)	0.60129 (10)	0.93578 (8)	0.0195 (3)
O42A	0.68542 (16)	0.69258 (10)	0.92218 (9)	0.0228 (3)
C5A	0.6291 (2)	0.62301 (13)	0.71860 (10)	0.0147 (3)
O5A	0.48477 (14)	0.68369 (9)	0.73264 (7)	0.0148 (3)
C51A	0.3524 (2)	0.70014 (14)	0.64674 (11)	0.0178 (3)
H51A	0.3028	0.6232	0.6250	0.023*
H51B	0.4088	0.7368	0.5921	0.023*
H51C	0.2567	0.7514	0.6655	0.023*
N1B	0.24025 (18)	0.53451 (11)	0.32375 (10)	0.0153 (3)
H1B	0.132 (2)	0.5114 (16)	0.2996 (14)	0.018*
C2B	0.3096 (2)	0.51884 (13)	0.41458 (12)	0.0149 (3)
H2B	0.260 (2)	0.4701 (15)	0.4623 (14)	0.018*
N3B	0.47439 (17)	0.57134 (12)	0.43354 (9)	0.0153 (3)
C4B	0.50660 (19)	0.62351 (12)	0.34835 (11)	0.0116 (3)
O4B	0.65256 (15)	0.68485 (9)	0.33247 (8)	0.0173 (3)
C41B	0.7821 (2)	0.69912 (15)	0.41801 (11)	0.0194 (4)
H41A	0.7284	0.7426	0.4702	0.025*
H41B	0.8847	0.7432	0.3986	0.025*
H41C	0.8211	0.6212	0.4434	0.025*
C5B	0.36094 (19)	0.60132 (13)	0.27712 (10)	0.0121 (3)
N5B	0.33021 (17)	0.63350 (10)	0.17595 (9)	0.0118 (3)
O51B	0.44495 (15)	0.69273 (10)	0.14108 (8)	0.0186 (3)
O52B	0.19160 (15)	0.59979 (10)	0.12861 (8)	0.0196 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0165 (7)	0.0131 (6)	0.0098 (6)	0.0040 (5)	0.0025 (5)	−0.0021 (4)
C2A	0.0209 (9)	0.0162 (7)	0.0104 (7)	−0.0025 (6)	−0.0025 (6)	−0.0035 (5)
N3A	0.0111 (6)	0.0204 (6)	0.0088 (6)	0.0009 (5)	−0.0020 (5)	0.0001 (5)
C4A	0.0211 (9)	0.0139 (7)	0.0101 (7)	−0.0049 (6)	0.0014 (6)	−0.0001 (5)
N4A	0.0118 (6)	0.0209 (7)	0.0168 (7)	0.0030 (5)	−0.0002 (5)	0.0077 (5)
O41A	0.0121 (6)	0.0296 (6)	0.0156 (6)	0.0030 (5)	−0.0036 (4)	−0.0045 (4)
O42A	0.0193 (6)	0.0301 (7)	0.0195 (6)	0.0039 (5)	0.0046 (5)	−0.0040 (5)
C5A	0.0216 (8)	0.0159 (7)	0.0081 (6)	−0.0032 (6)	0.0088 (6)	−0.0042 (5)
O5A	0.0133 (5)	0.0222 (6)	0.0079 (5)	0.0035 (4)	−0.0032 (4)	0.0005 (4)
C51A	0.0150 (8)	0.0219 (8)	0.0155 (8)	0.0039 (6)	−0.0027 (6)	−0.0016 (6)
N1B	0.0157 (7)	0.0149 (6)	0.0156 (6)	−0.0016 (5)	0.0027 (5)	−0.0003 (5)
C2B	0.0126 (7)	0.0181 (7)	0.0143 (7)	−0.0055 (6)	0.0027 (6)	−0.0022 (5)
N3B	0.0124 (6)	0.0208 (6)	0.0118 (6)	0.0025 (5)	−0.0033 (5)	−0.0007 (5)
C4B	0.0065 (7)	0.0113 (6)	0.0158 (7)	0.0001 (5)	−0.0043 (5)	−0.0061 (5)
O4B	0.0124 (6)	0.0222 (6)	0.0173 (6)	−0.0063 (4)	0.0018 (4)	0.0020 (4)
C41B	0.0162 (8)	0.0271 (9)	0.0138 (7)	−0.0074 (6)	−0.0043 (6)	0.0021 (6)
C5B	0.0067 (7)	0.0176 (7)	0.0118 (7)	−0.0043 (5)	0.0000 (5)	−0.0002 (5)
N5B	0.0129 (6)	0.0128 (6)	0.0096 (5)	0.0042 (5)	0.0004 (5)	0.0051 (4)
O51B	0.0141 (6)	0.0282 (6)	0.0131 (5)	−0.0054 (5)	−0.0002 (4)	0.0045 (4)
O52B	0.0189 (6)	0.0270 (6)	0.0117 (5)	−0.0031 (5)	−0.0043 (4)	−0.0054 (4)

Geometric parameters (Å, º)

N1A—C2A	1.347 (2)	N1B—C2B	1.293 (2)
N1A—C5A	1.3766 (18)	N1B—C5B	1.3840 (19)
N1A—H1A	0.810 (18)	N1B—H1B	0.890 (16)
C2A—N3A	1.3355 (19)	C2B—N3B	1.379 (2)
C2A—H2A	0.925 (19)	C2B—H2B	0.951 (18)
N3A—C4A	1.3705 (19)	N3B—C4B	1.335 (2)
C4A—C5A	1.367 (2)	C4B—O4B	1.3385 (18)
C4A—N4A	1.3948 (19)	C4B—C5B	1.4063 (19)
N4A—O42A	1.2477 (17)	O4B—C41B	1.4420 (18)
N4A—O41A	1.2629 (16)	C41B—H41A	0.9800
C5A—O5A	1.3183 (19)	C41B—H41B	0.9800
O5A—C51A	1.4616 (17)	C41B—H41C	0.9800
C51A—H51A	0.9800	C5B—N5B	1.4071 (18)
C51A—H51B	0.9800	N5B—O51B	1.2267 (16)
C51A—H51C	0.9800	N5B—O52B	1.2293 (16)
C2A—N1A—C5A	106.08 (13)	C2B—N1B—C5B	106.45 (13)
C2A—N1A—H1A	126.2 (13)	C2B—N1B—H1B	125.0 (13)
C5A—N1A—H1A	127.7 (13)	C5B—N1B—H1B	128.3 (13)
N3A—C2A—N1A	112.66 (14)	N1B—C2B—N3B	112.72 (14)
N3A—C2A—H2A	121.2 (11)	N1B—C2B—H2B	124.8 (11)
N1A—C2A—H2A	125.5 (11)	N3B—C2B—H2B	122.2 (11)
C2A—N3A—C4A	104.51 (13)	C4B—N3B—C2B	105.78 (12)
C5A—C4A—N3A	110.18 (12)	N3B—C4B—O4B	126.35 (13)
C5A—C4A—N4A	127.83 (14)	N3B—C4B—C5B	108.00 (13)
N3A—C4A—N4A	122.00 (14)	O4B—C4B—C5B	125.65 (13)
O42A—N4A—O41A	122.19 (13)	C4B—O4B—C41B	115.61 (11)
O42A—N4A—C4A	119.29 (13)	O4B—C41B—H41A	109.5
O41A—N4A—C4A	118.52 (13)	O4B—C41B—H41B	109.5
O5A—C5A—C4A	128.51 (13)	H41A—C41B—H41B	109.5
O5A—C5A—N1A	124.91 (14)	O4B—C41B—H41C	109.5
C4A—C5A—N1A	106.58 (13)	H41A—C41B—H41C	109.5
C5A—O5A—C51A	117.46 (11)	H41B—C41B—H41C	109.5
O5A—C51A—H51A	109.5	N1B—C5B—C4B	107.05 (13)
O5A—C51A—H51B	109.5	N1B—C5B—N5B	122.05 (13)
H51A—C51A—H51B	109.5	C4B—C5B—N5B	130.89 (14)
O5A—C51A—H51C	109.5	O51B—N5B—O52B	124.63 (12)
H51A—C51A—H51C	109.5	O51B—N5B—C5B	117.39 (12)
H51B—C51A—H51C	109.5	O52B—N5B—C5B	117.98 (12)
C5A—N1A—C2A—N3A	−0.25 (18)	C5B—N1B—C2B—N3B	−0.32 (18)
N1A—C2A—N3A—C4A	0.43 (17)	N1B—C2B—N3B—C4B	0.59 (18)
C2A—N3A—C4A—C5A	−0.45 (17)	C2B—N3B—C4B—O4B	−179.71 (14)
C2A—N3A—C4A—N4A	179.18 (14)	C2B—N3B—C4B—C5B	−0.60 (16)
C5A—C4A—N4A—O42A	−1.3 (2)	N3B—C4B—O4B—C41B	−2.9 (2)
N3A—C4A—N4A—O42A	179.09 (13)	C5B—C4B—O4B—C41B	178.12 (14)
C5A—C4A—N4A—O41A	179.07 (14)	C2B—N1B—C5B—C4B	−0.06 (16)
N3A—C4A—N4A—O41A	−0.5 (2)	C2B—N1B—C5B—N5B	178.74 (14)
N3A—C4A—C5A—O5A	−178.83 (14)	N3B—C4B—C5B—N1B	0.43 (16)
N4A—C4A—C5A—O5A	1.6 (3)	O4B—C4B—C5B—N1B	179.55 (13)
N3A—C4A—C5A—N1A	0.31 (17)	N3B—C4B—C5B—N5B	−178.23 (14)
N4A—C4A—C5A—N1A	−179.29 (14)	O4B—C4B—C5B—N5B	0.9 (3)
C2A—N1A—C5A—O5A	179.14 (14)	N1B—C5B—N5B—O51B	−179.91 (13)
C2A—N1A—C5A—C4A	−0.05 (16)	C4B—C5B—N5B—O51B	−1.4 (2)
C4A—C5A—O5A—C51A	177.22 (15)	N1B—C5B—N5B—O52B	−0.4 (2)
N1A—C5A—O5A—C51A	−1.8 (2)	C4B—C5B—N5B—O52B	178.05 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N3B	0.810 (18)	2.067 (19)	2.8702 (13)	171.3 (19)
C2A—H2A···O52B^i	0.925 (19)	2.496 (18)	3.1268 (17)	125.7 (14)
C51A—H51A···O52B^ii	0.98	2.66	3.6032 (16)	161
C51A—H51C···O51B^iii	0.98	2.43	3.3013 (16)	148
C51A—H51C···O4B^iii	0.98	2.56	3.3190 (16)	134
C51A—H51B···O52B^iv	0.98	2.83	3.4463 (17)	122
N1B—H1B···N3A^v	0.890 (16)	1.941 (17)	2.8306 (14)	177.1 (19)
C2B—H2B···O52B^ii	0.951 (18)	2.482 (18)	3.3832 (19)	158.1 (15)
C41B—H41A···O51B^iv	0.98	2.78	3.3595 (19)	118
C41B—H41B···O42A^vi	0.98	2.38	3.2792 (17)	153
C41B—H41B···O5A^vi	0.98	2.57	3.3366 (16)	135
C41B—H41C···O41A^vii	0.98	2.69	3.6101 (18)	157

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