N-(2-Chloro-eth-yl)morpholine-4-carbox-amide.

The title compound, C7H13ClN2O2, synthesized by the reaction of 2-chloro-ethyl iso-cyanate and morpholine, crystallizes with four molecules in the asymmetric unit, which have similar conformations and comprise two pairs each related by approximate non-crystallographic inversion centres. Two of them have a modest orientational disorder of the 2-chloro-ethyl fragments [occupancy ratio of 0.778 (4):0.222 (4)]. In the crystal, mol-ecules are linked by N-H⋯O=C hydrogen bonds, forming three crystallographically different kinds of infinite hydrogen-bonded chains extending along [001].

Related literature

For the solution-phase preparation of substituted morpholine derivatives, see: Lainton et al. (2003 ▶). For a related thio­morpholine analogue, see: Ujam et al. (2010 ▶); Henderson et al. (2006 ▶).

Experimental

Crystal data

C7H13ClN2O2

M = 192.64

Monoclinic,

a = 10.7393 (8) Å

b = 33.613 (3) Å

c = 9.9942 (7) Å

β = 95.704 (5)°

V = 3589.9 (5) Å3

Z = 16

Mo Kα radiation

μ = 0.39 mm−1

T = 99 K

0.30 × 0.10 × 0.10 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick 2003 ▶) T min = 0.892, T max = 0.962

39446 measured reflections

8451 independent reflections

5276 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.158

S = 1.04

8451 reflections

307 parameters

164 restraints

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.59 e Å−3

Absolute structure: Flack (1983 ▶), 4226 Friedel pairs

Absolute structure parameter: 0.38 (17)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814005832/qk2064sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005832/qk2064Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005832/qk2064Isup3.mol

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005832/qk2064Isup4.cml

CCDC reference: 991972

Additional supporting information: crystallographic information; 3D view; checkCIF report

C7H13ClN2O2	F(000) = 1632
Mr = 192.64	Dx = 1.426 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 10.7393 (8) Å	Cell parameters from 3770 reflections
b = 33.613 (3) Å	θ = 2–27°
c = 9.9942 (7) Å	µ = 0.39 mm−1
β = 95.704 (5)°	T = 99 K
V = 3589.9 (5) Å3	Needle, colourless
Z = 16	0.30 × 0.10 × 0.10 mm

Siemens SMART CCD diffractometer	5276 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.082
ω scans	θmax = 27.8°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick 2003)	h = −14→14
Tmin = 0.892, Tmax = 0.962	k = −43→44
39446 measured reflections	l = −13→13
8451 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059	H-atom parameters constrained
wR(F2) = 0.158	w = 1/[σ2(Fo2) + (0.0582P)2 + 2.927P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
8451 reflections	Δρmax = 0.56 e Å−3
307 parameters	Δρmin = −0.59 e Å−3
164 restraints	Absolute structure: Flack (1983), 4226 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.38 (17)

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. Refined as a 2-component inversion twin (here a polar twin) with a component ratio of 0.38/0.62. The final refinement restrained the four independent molecules to similar geometry using the SAME command of SHELXL, and EADP constraints were applied to equivalent atom pairs related by pseudosymmetry. Some residual electron density appeared to arise from partial disorder of the ethylene groups of two of the molecules over two sites (0.78:0.22) so the C atoms of the minor component were included with fixed isotropic thermal parameters.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.1793 (6)	0.69065 (18)	0.5906 (7)	0.0257 (6)
H1A	0.2429	0.6694	0.5886	0.031*
H1B	0.1907	0.7095	0.5168	0.031*
C2	0.0503 (6)	0.67256 (17)	0.5692 (6)	0.0295 (6)
H2A	−0.0133	0.6940	0.5615	0.035*
H2B	0.0420	0.6572	0.4843	0.035*
C3	0.0387 (5)	0.66860 (16)	0.8026 (6)	0.0299 (6)
H3A	0.0211	0.6505	0.8767	0.036*
H3B	−0.0244	0.6901	0.7973	0.036*
C4	0.1672 (5)	0.68631 (15)	0.8331 (6)	0.0245 (6)
H4A	0.1701	0.7025	0.9161	0.029*
H4B	0.2300	0.6648	0.8478	0.029*
C5	0.2610 (4)	0.74577 (14)	0.7460 (5)	0.0216 (5)
C6	0.3614 (4)	0.80530 (13)	0.6609 (5)	0.0241 (6)
H6A	0.3323	0.8190	0.7397	0.029*
H6B	0.3423	0.8225	0.5810	0.029*
C7	0.4988 (4)	0.79800 (13)	0.6835 (6)	0.0317 (7)
H7A	0.5272	0.7829	0.6070	0.038*
H7B	0.5187	0.7822	0.7666	0.038*
N1	0.1972 (4)	0.71155 (12)	0.7195 (5)	0.0201 (5)
N2	0.2967 (4)	0.76644 (11)	0.6398 (4)	0.0308 (5)
H2C	0.2820 (5)	0.7572 (2)	0.5612 (18)	0.030*
O1	0.0284 (3)	0.64694 (11)	0.6785 (4)	0.0297 (4)
O2	0.2846 (3)	0.75889 (10)	0.8630 (4)	0.0292 (4)
Cl1	0.57778 (12)	0.84633 (4)	0.69906 (14)	0.0372 (2)
C8	0.6779 (6)	0.56216 (18)	1.0240 (7)	0.0257 (6)
H8A	0.6654	0.5439	1.0993	0.031*
H8B	0.6127	0.5830	1.0210	0.031*
C9	0.8058 (6)	0.58091 (17)	1.0459 (6)	0.0295 (6)
H9A	0.8108	0.5971	1.1291	0.035*
H9B	0.8695	0.5596	1.0592	0.035*
C10	0.8262 (5)	0.58296 (16)	0.8153 (6)	0.0299 (6)
H10A	0.8900	0.5616	0.8237	0.036*
H10B	0.8445	0.6005	0.7401	0.036*
C11	0.6986 (5)	0.56463 (15)	0.7835 (6)	0.0245 (6)
H11A	0.6352	0.5859	0.7661	0.029*
H11B	0.6979	0.5481	0.7016	0.029*
C12	0.5946 (4)	0.50722 (14)	0.8711 (5)	0.0216 (5)
C13	0.4970 (5)	0.44776 (15)	0.9575 (6)	0.0241 (6)	0.778 (4)
H13A	0.5150	0.4313	1.0393	0.029*
H13B	0.5310	0.4340	0.8815	0.029*
C14	0.3576 (5)	0.45371 (16)	0.9277 (7)	0.0317 (7)	0.778 (4)
H14A	0.3393	0.4683	0.8420	0.038*
H14B	0.3249	0.4694	1.0004	0.038*
N3	0.6675 (4)	0.54001 (12)	0.8967 (5)	0.0201 (5)
N4	0.5548 (4)	0.48731 (11)	0.9778 (4)	0.0308 (5)
H4C	0.5635 (4)	0.4978 (3)	1.0565 (18)	0.030*
O3	0.8346 (3)	0.60560 (10)	0.9370 (4)	0.0297 (4)
O4	0.5687 (3)	0.49474 (11)	0.7551 (4)	0.0292 (4)
Cl2	0.28368 (12)	0.40510 (4)	0.91603 (15)	0.0372 (2)
C15	0.1664 (6)	0.81124 (18)	0.0959 (7)	0.0268 (6)
H15A	0.1830	0.7940	0.0194	0.032*
H15B	0.2269	0.8335	0.1003	0.032*
C16	0.0353 (6)	0.82743 (18)	0.0734 (6)	0.0317 (6)
H16A	0.0273	0.8440	−0.0089	0.038*
H16B	−0.0244	0.8050	0.0592	0.038*
C17	0.0137 (5)	0.82715 (16)	0.3030 (6)	0.0283 (6)
H17A	−0.0465	0.8048	0.2915	0.034*
H17B	−0.0088	0.8437	0.3790	0.034*
C18	0.1445 (5)	0.81076 (16)	0.3359 (6)	0.0245 (6)
H18A	0.2035	0.8330	0.3580	0.029*
H18B	0.1461	0.7932	0.4156	0.029*
C19	0.2757 (4)	0.76025 (14)	0.2480 (5)	0.0220 (5)
C20	0.4416 (4)	0.71961 (12)	0.1643 (5)	0.0251 (6)
H20A	0.4928	0.7283	0.2470	0.030*
H20B	0.4929	0.7226	0.0879	0.030*
C21	0.4066 (4)	0.67709 (12)	0.1778 (6)	0.0270 (6)
H21A	0.3554	0.6680	0.0956	0.032*
H21B	0.3571	0.6736	0.2554	0.032*
N5	0.1841 (4)	0.78819 (12)	0.2215 (5)	0.0199 (4)
N6	0.3293 (4)	0.74516 (11)	0.1419 (4)	0.0298 (5)
H6C	0.2982 (8)	0.75040 (16)	0.0619 (18)	0.030*
O5	0.0041 (4)	0.85058 (10)	0.1835 (4)	0.0321 (4)
O6	0.3081 (3)	0.74858 (11)	0.3645 (4)	0.0281 (4)
Cl3	0.55040 (11)	0.64849 (4)	0.20263 (14)	0.03441 (18)
C22	0.6776 (6)	0.94101 (19)	0.5227 (7)	0.0268 (6)
H22A	0.6175	0.9186	0.5190	0.032*
H22B	0.6605	0.9586	0.5981	0.032*
C23	0.8101 (6)	0.92532 (18)	0.5449 (6)	0.0317 (6)
H23A	0.8690	0.9480	0.5557	0.038*
H23B	0.8199	0.9095	0.6289	0.038*
C24	0.8292 (5)	0.92350 (16)	0.3134 (6)	0.0283 (6)
H24A	0.8502	0.9064	0.2382	0.034*
H24B	0.8895	0.9459	0.3216	0.034*
C25	0.6977 (5)	0.93984 (16)	0.2819 (6)	0.0245 (6)
H25A	0.6942	0.9568	0.2006	0.029*
H25B	0.6380	0.9176	0.2637	0.029*
C26	0.5745 (5)	0.99248 (14)	0.3691 (5)	0.0220 (5)
C27	0.4059 (5)	1.03184 (15)	0.4504 (6)	0.0251 (6)	0.778 (4)
H27A	0.3535	1.0278	0.5254	0.030*
H27B	0.3574	1.0232	0.3660	0.030*
C28	0.4398 (5)	1.07526 (15)	0.4409 (6)	0.0270 (6)	0.778 (4)
H28A	0.4897	1.0796	0.3641	0.032*
H28B	0.4900	1.0839	0.5242	0.032*
N7	0.6630 (4)	0.96323 (12)	0.3958 (5)	0.0199 (4)
N8	0.5208 (4)	1.00824 (11)	0.4736 (4)	0.0298 (5)
H8C	0.5529 (8)	1.00457 (14)	0.5510 (18)	0.030*
O7	0.8412 (4)	0.90094 (10)	0.4351 (4)	0.0321 (4)
O8	0.5435 (3)	1.00387 (11)	0.2531 (4)	0.0281 (4)
Cl4	0.29550 (11)	1.10319 (3)	0.41732 (14)	0.03441 (18)
C13A	0.421 (2)	0.4712 (5)	0.954 (2)	0.030*	0.222 (4)
C14A	0.442 (2)	0.4253 (5)	0.939 (2)	0.030*	0.222 (4)
C27A	0.4955 (18)	1.0541 (6)	0.460 (2)	0.030*	0.222 (4)
C28A	0.3506 (17)	1.0513 (6)	0.427 (2)	0.030*	0.222 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0285 (14)	0.0265 (13)	0.0224 (14)	−0.0047 (11)	0.0047 (11)	−0.0045 (11)
C2	0.0326 (15)	0.0302 (14)	0.0251 (15)	−0.0090 (12)	0.0001 (11)	0.0000 (11)
C3	0.0297 (15)	0.0330 (13)	0.0280 (15)	−0.0047 (12)	0.0074 (12)	0.0043 (11)
C4	0.0281 (15)	0.0246 (12)	0.0203 (13)	−0.0047 (11)	0.0006 (11)	0.0037 (10)
C5	0.0194 (12)	0.0249 (12)	0.0204 (13)	0.0015 (10)	0.0019 (10)	0.0010 (10)
C6	0.0223 (14)	0.0251 (14)	0.0244 (14)	0.0013 (12)	0.0005 (11)	0.0010 (11)
C7	0.0235 (15)	0.0299 (14)	0.0420 (18)	0.0007 (12)	0.0056 (13)	0.0004 (13)
N1	0.0217 (12)	0.0223 (10)	0.0170 (11)	−0.0050 (9)	0.0049 (9)	−0.0001 (8)
N2	0.0403 (13)	0.0351 (12)	0.0168 (11)	−0.0182 (10)	0.0019 (9)	−0.0016 (9)
O1	0.0318 (11)	0.0288 (9)	0.0282 (11)	−0.0122 (8)	0.0021 (8)	0.0027 (8)
O2	0.0414 (11)	0.0290 (9)	0.0172 (9)	−0.0094 (8)	0.0037 (8)	−0.0030 (7)
Cl1	0.0332 (4)	0.0381 (4)	0.0398 (4)	−0.0168 (3)	0.0012 (3)	−0.0013 (3)
C8	0.0285 (14)	0.0265 (13)	0.0224 (14)	−0.0047 (11)	0.0047 (11)	−0.0045 (11)
C9	0.0326 (15)	0.0302 (14)	0.0251 (15)	−0.0090 (12)	0.0001 (11)	0.0000 (11)
C10	0.0297 (15)	0.0330 (13)	0.0280 (15)	−0.0047 (12)	0.0074 (12)	0.0043 (11)
C11	0.0281 (15)	0.0246 (12)	0.0203 (13)	−0.0047 (11)	0.0006 (11)	0.0037 (10)
C12	0.0194 (12)	0.0249 (12)	0.0204 (13)	0.0015 (10)	0.0019 (10)	0.0010 (10)
C13	0.0223 (14)	0.0251 (14)	0.0244 (14)	0.0013 (12)	0.0005 (11)	0.0010 (11)
C14	0.0235 (15)	0.0299 (14)	0.0420 (18)	0.0007 (12)	0.0056 (13)	0.0004 (13)
N3	0.0217 (12)	0.0223 (10)	0.0170 (11)	−0.0050 (9)	0.0049 (9)	−0.0001 (8)
N4	0.0403 (13)	0.0351 (12)	0.0168 (11)	−0.0182 (10)	0.0019 (9)	−0.0016 (9)
O3	0.0318 (11)	0.0288 (9)	0.0282 (11)	−0.0122 (8)	0.0021 (8)	0.0027 (8)
O4	0.0414 (11)	0.0290 (9)	0.0172 (9)	−0.0094 (8)	0.0037 (8)	−0.0030 (7)
Cl2	0.0332 (4)	0.0381 (4)	0.0398 (4)	−0.0168 (3)	0.0012 (3)	−0.0013 (3)
C15	0.0322 (16)	0.0287 (13)	0.0202 (14)	0.0083 (12)	0.0063 (11)	0.0035 (10)
C16	0.0370 (16)	0.0325 (14)	0.0244 (15)	0.0131 (12)	−0.0034 (12)	−0.0021 (11)
C17	0.0247 (14)	0.0296 (13)	0.0310 (15)	0.0063 (11)	0.0056 (11)	−0.0024 (11)
C18	0.0249 (14)	0.0261 (12)	0.0227 (14)	0.0040 (11)	0.0042 (11)	−0.0027 (10)
C19	0.0245 (13)	0.0234 (12)	0.0185 (13)	−0.0012 (10)	0.0043 (10)	−0.0012 (10)
C20	0.0209 (15)	0.0286 (13)	0.0271 (15)	−0.0016 (12)	0.0082 (11)	−0.0033 (11)
C21	0.0211 (15)	0.0274 (14)	0.0322 (16)	−0.0013 (12)	0.0005 (12)	−0.0019 (12)
N5	0.0233 (11)	0.0192 (9)	0.0175 (11)	0.0023 (8)	0.0028 (8)	0.0001 (8)
N6	0.0396 (13)	0.0344 (11)	0.0156 (11)	0.0191 (10)	0.0035 (9)	0.0012 (9)
O5	0.0360 (11)	0.0303 (9)	0.0293 (11)	0.0126 (8)	0.0001 (8)	−0.0031 (8)
O6	0.0343 (10)	0.0338 (9)	0.0163 (9)	0.0116 (8)	0.0031 (7)	0.0021 (7)
Cl3	0.0318 (4)	0.0353 (3)	0.0355 (4)	0.0150 (3)	0.0002 (3)	−0.0016 (3)
C22	0.0322 (16)	0.0287 (13)	0.0202 (14)	0.0083 (12)	0.0063 (11)	0.0035 (10)
C23	0.0370 (16)	0.0325 (14)	0.0244 (15)	0.0131 (12)	−0.0034 (12)	−0.0021 (11)
C24	0.0247 (14)	0.0296 (13)	0.0310 (15)	0.0063 (11)	0.0056 (11)	−0.0024 (11)
C25	0.0249 (14)	0.0261 (12)	0.0227 (14)	0.0040 (11)	0.0042 (11)	−0.0027 (10)
C26	0.0245 (13)	0.0234 (12)	0.0185 (13)	−0.0012 (10)	0.0043 (10)	−0.0012 (10)
C27	0.0209 (15)	0.0286 (13)	0.0271 (15)	−0.0016 (12)	0.0082 (11)	−0.0033 (11)
C28	0.0211 (15)	0.0274 (14)	0.0322 (16)	−0.0013 (12)	0.0005 (12)	−0.0019 (12)
N7	0.0233 (11)	0.0192 (9)	0.0175 (11)	0.0023 (8)	0.0028 (8)	0.0001 (8)
N8	0.0396 (13)	0.0344 (11)	0.0156 (11)	0.0191 (10)	0.0035 (9)	0.0012 (9)
O7	0.0360 (11)	0.0303 (9)	0.0293 (11)	0.0126 (8)	0.0001 (8)	−0.0031 (8)
O8	0.0343 (10)	0.0338 (9)	0.0163 (9)	0.0116 (8)	0.0031 (7)	0.0021 (7)
Cl4	0.0318 (4)	0.0353 (3)	0.0355 (4)	0.0150 (3)	0.0002 (3)	−0.0016 (3)

C1—N1	1.463 (6)	C15—C16	1.506 (7)
C1—C2	1.509 (7)	C16—O5	1.415 (6)
C2—O1	1.429 (6)	C17—O5	1.426 (6)
C3—O1	1.433 (6)	C17—C18	1.514 (6)
C3—C4	1.506 (6)	C18—N5	1.470 (6)
C4—N1	1.478 (6)	C19—O6	1.244 (6)
C5—O2	1.252 (6)	C19—N6	1.354 (6)
C5—N1	1.352 (6)	C19—N5	1.367 (6)
C5—N2	1.355 (6)	C20—N6	1.480 (5)
C6—N2	1.485 (5)	C20—C21	1.487 (5)
C6—C7	1.491 (5)	C21—Cl3	1.815 (5)
C7—Cl1	1.832 (4)	C22—N7	1.467 (6)
C8—N3	1.469 (6)	C22—C23	1.513 (7)
C8—C9	1.507 (7)	C23—O7	1.435 (6)
C9—O3	1.427 (6)	C24—O7	1.428 (6)
C10—O3	1.430 (6)	C24—C25	1.519 (6)
C10—C11	1.507 (6)	C25—N7	1.462 (6)
C11—N3	1.466 (6)	C26—O8	1.235 (5)
C12—O4	1.239 (6)	C26—N8	1.351 (6)
C12—N3	1.362 (6)	C26—N7	1.375 (6)
C12—N4	1.362 (6)	C27—N8	1.466 (6)
C13—N4	1.473 (6)	C27—C28	1.509 (7)
C13—C14	1.510 (7)	C28—Cl4	1.807 (5)
C14—Cl2	1.815 (5)	C13A—C14A	1.568 (16)
C15—N5	1.471 (6)	C27A—C28A	1.561 (17)
N1—C1—C2	110.9 (5)	N5—C15—C16	110.9 (5)
O1—C2—C1	110.7 (5)	O5—C16—C15	111.9 (5)
O1—C3—C4	111.5 (5)	O5—C17—C18	111.8 (5)
N1—C4—C3	109.7 (5)	N5—C18—C17	110.7 (5)
O2—C5—N1	122.3 (5)	O6—C19—N6	120.9 (4)
O2—C5—N2	120.3 (4)	O6—C19—N5	121.8 (5)
N1—C5—N2	117.4 (5)	N6—C19—N5	117.3 (5)
N2—C6—C7	108.6 (4)	N6—C20—C21	111.2 (4)
C6—C7—Cl1	108.0 (3)	C20—C21—Cl3	107.6 (3)
C5—N1—C1	126.9 (5)	C19—N5—C18	117.6 (5)
C5—N1—C4	118.9 (5)	C19—N5—C15	123.8 (5)
C1—N1—C4	112.4 (4)	C18—N5—C15	111.6 (4)
C5—N2—C6	120.3 (4)	C19—N6—C20	120.1 (4)
C2—O1—C3	110.6 (4)	C16—O5—C17	110.2 (4)
N3—C8—C9	109.1 (5)	N7—C22—C23	108.8 (5)
O3—C9—C8	113.4 (5)	O7—C23—C22	112.0 (5)
O3—C10—C11	112.1 (5)	O7—C24—C25	111.8 (5)
N3—C11—C10	109.9 (5)	N7—C25—C24	109.7 (5)
O4—C12—N3	121.4 (5)	O8—C26—N8	120.5 (4)
O4—C12—N4	120.5 (4)	O8—C26—N7	121.4 (5)
N3—C12—N4	118.1 (5)	N8—C26—N7	118.0 (5)
N4—C13—C14	107.7 (4)	N8—C27—C28	109.2 (4)
C13—C14—Cl2	108.2 (4)	C27—C28—Cl4	107.5 (4)
C12—N3—C11	118.9 (5)	C26—N7—C25	117.3 (5)
C12—N3—C8	124.4 (5)	C26—N7—C22	123.0 (5)
C11—N3—C8	112.3 (4)	C25—N7—C22	112.7 (4)
C12—N4—C13	119.8 (4)	C26—N8—C27	120.5 (4)
C9—O3—C10	109.8 (4)	C24—O7—C23	109.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O6	0.85	2.03	2.831 (6)	157
N4—H4C···O4i	0.86	2.00	2.826 (6)	162
N6—H6C···O2ii	0.85	2.00	2.819 (6)	161
N8—H8C···O8iii	0.82	2.05	2.809 (6)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2C⋯O6	0.85	2.03	2.831 (6)	157
N4—H4C⋯O4i	0.86	2.00	2.826 (6)	162
N6—H6C⋯O2ii	0.85	2.00	2.819 (6)	161
N8—H8C⋯O8iii	0.82	2.05	2.809 (6)	153

Symmetry codes: (i) ; (ii) ; (iii) .