Glycoluril di­amide dihydrate

The crystal structure of the title compound, cis-N,N'-bis(2-hydroxy­ethyl)-4,8-dioxo-2,6-dioxa-3a,4a,7a,8a-tetra­aza­cyclo­penta­[def]­fluorene-8b,8c-dicarbox­amide dihydrate, C₁₄H₂₀N₆O₈·2H₂O, is reported. The compound forms tape-like structures comprising 14- and 10-membered hydrogen-bonded rings. These hydrogen-bonded tapes form hydrogen-bonded sheets and stacks of sheets by hydrogen-bonding interactions with the solvent water mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 203 K
• Mean [sigma](C-C) = 0.001 Å
• Disorder in solvent or counterion
• R factor = 0.034
• wR factor = 0.098
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      33.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXTL.

cis-N,N'-bis(2-hydroxyethyl)-4,8-dioxo-2,6-dioxa-3a,4a,7a,8a- tetraazacyclopenta[def]fluorene-8 b,8c-dicarboxamide dihydrate

Crystal data

C14H20N6O8·2H2O	F(000) = 1840
Mr = 436.39	Dx = 1.541 Mg m^−3
Monoclinic, C2/c	Melting point = 276–279 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 28.0466 (14) Å	Cell parameters from 7457 reflections
b = 9.0833 (4) Å	θ = 2.4–30.0°
c = 14.7948 (7) Å	µ = 0.13 mm^−1
β = 93.587 (1)°	T = 203 K
V = 3761.7 (3) Å^3	Block, colorless
Z = 8	0.50 × 0.42 × 0.36 mm

Data collection

Bruker SMART CCD area-detector diffractometer	5486 independent reflections
Radiation source: fine-focus sealed tube	4948 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 30.0°, θmin = 2.4°
Absorption correction: multi-scan (Blessing, 1995)	h = −38→39
Tmin = 0.938, Tmax = 0.954	k = −12→12
36186 measured reflections	l = −20→20

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0609P)^2 + 1.3549P] where P = (Fo^2 + 2Fc^2)/3
5486 reflections	(Δ/σ)max = 0.001
380 parameters	Δρmax = 0.37 e Å^−3
1 restraint	Δρmin = −0.21 e Å^−3

Special details

Experimental. One water molecule was refined as two partial occupancy overlapping moieties (O12, O13).

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)
C1	0.37387 (3)	0.73850 (8)	0.20556 (5)	0.02968 (15)
H1A	0.3687 (4)	0.8381 (12)	0.2322 (7)	0.033 (2)*
H1B	0.3961 (4)	0.6827 (12)	0.2433 (7)	0.033 (3)*
C1A	0.36365 (2)	0.82417 (7)	0.04842 (4)	0.01743 (11)
C1B	0.36353 (2)	0.99363 (7)	0.05670 (4)	0.01916 (11)
C1C	0.31877 (3)	1.22183 (7)	0.04106 (5)	0.02681 (14)
H1C1	0.3482 (4)	1.2584 (12)	0.0211 (7)	0.034 (3)*
H1C2	0.2935 (4)	1.2537 (12)	−0.0015 (8)	0.035 (3)*
C1D	0.31140 (3)	1.28008 (9)	0.13520 (6)	0.03378 (17)
H1D1	0.3152 (5)	1.3893 (16)	0.1313 (8)	0.051 (3)*
H1D2	0.3352 (4)	1.2357 (13)	0.1802 (8)	0.039 (3)*
N1	0.39522 (2)	0.75929 (6)	0.11942 (4)	0.02266 (11)
H1	0.2954 (4)	1.0098 (12)	0.0280 (7)	0.030 (2)*
N1B	0.32192 (2)	1.06079 (6)	0.03901 (4)	0.02215 (11)
O1B	0.401717 (18)	1.05661 (6)	0.07650 (4)	0.02667 (11)
O1D	0.26446 (2)	1.24984 (7)	0.16287 (5)	0.03978 (14)
H1D	0.2673 (5)	1.1691 (17)	0.1967 (9)	0.061 (4)*
C2	0.42251 (2)	0.64749 (7)	0.08476 (5)	0.02391 (13)
C2A	0.38407 (2)	0.76428 (7)	−0.04118 (4)	0.01754 (11)
C2B	0.40204 (2)	0.88509 (7)	−0.10424 (4)	0.01984 (12)
C2C	0.47016 (2)	1.03136 (8)	−0.14385 (5)	0.02559 (14)
H2C1	0.5046 (4)	1.0167 (12)	−0.1388 (7)	0.034 (3)*
H2C2	0.4596 (3)	1.0240 (11)	−0.2064 (7)	0.027 (2)*
C2D	0.45767 (3)	1.18258 (8)	−0.10800 (5)	0.02645 (14)
H2D1	0.4236 (4)	1.1977 (12)	−0.1169 (7)	0.028 (2)*
H2D2	0.4739 (4)	1.2562 (12)	−0.1432 (7)	0.036 (3)*
N2	0.421982 (19)	0.66524 (6)	−0.00784 (4)	0.02127 (11)
H2	0.4664 (3)	0.8642 (11)	−0.0558 (7)	0.027 (2)*
N2B	0.44844 (2)	0.91279 (6)	−0.09413 (4)	0.02098 (11)
O2	0.44511 (2)	0.55537 (7)	0.12906 (4)	0.03598 (13)
O2B	0.373452 (19)	0.95101 (6)	−0.15631 (4)	0.02966 (11)
O2D	0.472674 (18)	1.20134 (6)	−0.01472 (4)	0.02756 (11)
H2D	0.4511 (5)	1.1625 (15)	0.0157 (9)	0.051 (3)*
C3	0.43325 (3)	0.54469 (8)	−0.06786 (5)	0.02801 (15)
H3A	0.4541 (4)	0.4789 (12)	−0.0366 (7)	0.032 (3)*
H3B	0.4483 (4)	0.5860 (12)	−0.1208 (7)	0.028 (2)*
O3	0.39071 (2)	0.46702 (6)	−0.09657 (4)	0.02993 (12)
C4	0.35748 (3)	0.56383 (8)	−0.14330 (5)	0.02778 (14)
H4A	0.3723 (4)	0.6034 (12)	−0.1944 (7)	0.033 (3)*
H4B	0.3289 (4)	0.5091 (12)	−0.1622 (7)	0.032 (3)*
N4	0.344093 (19)	0.68254 (6)	−0.08385 (4)	0.02019 (11)
C5	0.30976 (2)	0.65630 (7)	−0.02198 (4)	0.01972 (12)
N5	0.316242 (19)	0.75896 (6)	0.04700 (4)	0.01950 (10)
O5	0.278291 (18)	0.56426 (6)	−0.02931 (4)	0.02762 (11)
C6	0.29695 (3)	0.73536 (8)	0.13479 (5)	0.02634 (14)
H6A	0.2677 (4)	0.6758 (12)	0.1254 (7)	0.032 (2)*
H6B	0.2905 (4)	0.8348 (12)	0.1603 (7)	0.032 (2)*
O6	0.33038 (2)	0.65772 (6)	0.19346 (3)	0.03059 (12)
O11	0.27876 (2)	1.01451 (7)	0.28387 (4)	0.03447 (13)
H11A	0.2680 (5)	0.9293 (17)	0.3039 (9)	0.058 (4)*
H11B	0.3074 (5)	1.0239 (16)	0.3112 (9)	0.052 (3)*
O12	0.43904 (7)	0.27734 (18)	0.21124 (11)	0.0464 (4)	0.50
H12A	0.4483 (7)	0.3599 (19)	0.1832 (12)	0.090 (6)*	0.50
H12B	0.4239 (10)	0.203 (3)	0.1746 (19)	0.060 (8)*	0.50
O13	0.45914 (9)	0.2781 (3)	0.22596 (18)	0.0769 (7)	0.50
H13A	0.4483 (7)	0.3599 (19)	0.1832 (12)	0.090 (6)*	0.50
H13B	0.4951 (8)	0.296 (3)	0.234 (3)	0.088 (11)*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0427 (4)	0.0266 (3)	0.0194 (3)	−0.0040 (3)	−0.0012 (3)	0.0008 (2)
C1A	0.0181 (2)	0.0149 (2)	0.0193 (2)	−0.00134 (19)	0.00075 (19)	0.00037 (19)
C1B	0.0216 (3)	0.0157 (2)	0.0204 (2)	−0.0014 (2)	0.0035 (2)	−0.0008 (2)
C1C	0.0280 (3)	0.0157 (3)	0.0370 (3)	0.0016 (2)	0.0043 (3)	0.0025 (2)
C1D	0.0387 (4)	0.0206 (3)	0.0418 (4)	0.0010 (3)	0.0008 (3)	−0.0067 (3)
N1	0.0266 (3)	0.0199 (2)	0.0208 (2)	0.0001 (2)	−0.0037 (2)	0.00176 (19)
N1B	0.0213 (2)	0.0157 (2)	0.0295 (3)	−0.00040 (19)	0.0023 (2)	−0.00048 (19)
O1B	0.0217 (2)	0.0209 (2)	0.0374 (3)	−0.00485 (17)	0.00208 (19)	−0.00279 (19)
O1D	0.0442 (3)	0.0344 (3)	0.0420 (3)	0.0113 (3)	0.0123 (3)	0.0017 (2)
C2	0.0224 (3)	0.0190 (3)	0.0296 (3)	−0.0012 (2)	−0.0038 (2)	0.0034 (2)
C2A	0.0168 (2)	0.0153 (2)	0.0206 (2)	0.00091 (19)	0.00126 (19)	0.00061 (19)
C2B	0.0208 (3)	0.0174 (2)	0.0216 (3)	0.0017 (2)	0.0040 (2)	0.0012 (2)
C2C	0.0244 (3)	0.0231 (3)	0.0300 (3)	−0.0014 (2)	0.0079 (2)	0.0051 (2)
C2D	0.0267 (3)	0.0206 (3)	0.0317 (3)	−0.0012 (2)	−0.0006 (3)	0.0054 (2)
N2	0.0193 (2)	0.0167 (2)	0.0278 (3)	0.00337 (18)	0.00147 (19)	0.00249 (19)
N2B	0.0198 (2)	0.0188 (2)	0.0247 (2)	0.00124 (19)	0.00396 (19)	0.00348 (19)
O2	0.0381 (3)	0.0282 (3)	0.0403 (3)	0.0074 (2)	−0.0084 (2)	0.0100 (2)
O2B	0.0245 (2)	0.0306 (2)	0.0336 (3)	0.0023 (2)	−0.00060 (19)	0.0124 (2)
O2D	0.0233 (2)	0.0267 (2)	0.0323 (2)	−0.00401 (19)	−0.00067 (19)	0.0022 (2)
C3	0.0264 (3)	0.0201 (3)	0.0381 (4)	0.0058 (2)	0.0064 (3)	−0.0015 (3)
O3	0.0334 (3)	0.0185 (2)	0.0380 (3)	0.00239 (19)	0.0035 (2)	−0.00552 (19)
C4	0.0327 (3)	0.0251 (3)	0.0255 (3)	0.0016 (3)	0.0017 (3)	−0.0075 (2)
N4	0.0202 (2)	0.0189 (2)	0.0214 (2)	−0.00102 (19)	0.00079 (18)	−0.00319 (18)
C5	0.0186 (2)	0.0167 (2)	0.0236 (3)	0.0002 (2)	−0.0005 (2)	0.0001 (2)
N5	0.0197 (2)	0.0170 (2)	0.0221 (2)	−0.00359 (18)	0.00423 (18)	−0.00121 (18)
O5	0.0229 (2)	0.0229 (2)	0.0369 (3)	−0.00644 (18)	0.00028 (19)	−0.00313 (19)
C6	0.0311 (3)	0.0235 (3)	0.0255 (3)	−0.0035 (3)	0.0100 (2)	0.0012 (2)
O6	0.0423 (3)	0.0253 (2)	0.0246 (2)	−0.0051 (2)	0.0048 (2)	0.00526 (19)
O11	0.0263 (2)	0.0308 (3)	0.0464 (3)	−0.0006 (2)	0.0028 (2)	0.0013 (2)
O12	0.0656 (10)	0.0345 (7)	0.0386 (7)	−0.0124 (7)	0.0002 (7)	0.0005 (5)
O13	0.0775 (15)	0.0603 (11)	0.0912 (16)	−0.0139 (11)	−0.0077 (12)	0.0333 (11)

Geometric parameters (Å, º)

C1—O6	1.4250 (10)	C2C—H2C1	0.973 (11)
C1—N1	1.4540 (9)	C2C—H2C2	0.957 (10)
C1—H1A	1.001 (11)	C2D—O2D	1.4277 (9)
C1—H1B	0.956 (11)	C2D—H2D1	0.965 (10)
C1A—N5	1.4545 (8)	C2D—H2D2	0.978 (11)
C1A—N1	1.4555 (8)	N2—C3	1.4568 (9)
C1A—C1B	1.5441 (8)	N2B—H2	0.857 (10)
C1A—C2A	1.5736 (8)	O2D—H2D	0.853 (14)
C1B—O1B	1.2332 (8)	C3—O3	1.4277 (9)
C1B—N1B	1.3285 (8)	C3—H3A	0.938 (11)
C1C—N1B	1.4659 (9)	C3—H3B	0.988 (10)
C1C—C1D	1.5161 (11)	O3—C4	1.4281 (9)
C1C—H1C1	0.953 (11)	C4—N4	1.4555 (9)
C1C—H1C2	0.964 (11)	C4—H4A	0.955 (11)
C1D—O1D	1.4297 (11)	C4—H4B	0.969 (11)
C1D—H1D1	0.999 (14)	N4—C5	1.3900 (8)
C1D—H1D2	0.998 (11)	C5—O5	1.2156 (8)
N1—C2	1.3889 (9)	C5—N5	1.3860 (8)
N1B—H1	0.882 (11)	N5—C6	1.4539 (9)
O1D—H1D	0.888 (15)	C6—O6	1.4241 (9)
C2—O2	1.2164 (9)	C6—H6A	0.985 (11)
C2—N2	1.3787 (9)	C6—H6B	1.000 (11)
C2A—N2	1.4551 (8)	O11—H11A	0.888 (15)
C2A—N4	1.4555 (8)	O11—H11B	0.881 (13)
C2A—C2B	1.5452 (9)	O12—H12A	0.903 (17)
C2B—O2B	1.2319 (8)	O12—H12B	0.95 (3)
C2B—N2B	1.3247 (8)	O13—H13A	1.010 (16)
C2C—N2B	1.4588 (9)	O13—H13B	1.02 (2)
C2C—C2D	1.5212 (10)
O6—C1—N1	110.67 (6)	N2B—C2C—H2C2	108.8 (6)
O6—C1—H1A	111.7 (6)	C2D—C2C—H2C2	109.7 (6)
N1—C1—H1A	107.8 (6)	H2C1—C2C—H2C2	108.1 (9)
O6—C1—H1B	108.8 (7)	O2D—C2D—C2C	112.61 (6)
N1—C1—H1B	107.0 (6)	O2D—C2D—H2D1	110.2 (6)
H1A—C1—H1B	110.8 (9)	C2C—C2D—H2D1	109.1 (6)
N5—C1A—N1	111.09 (5)	O2D—C2D—H2D2	108.3 (6)
N5—C1A—C1B	113.62 (5)	C2C—C2D—H2D2	107.8 (7)
N1—C1A—C1B	110.52 (5)	H2D1—C2D—H2D2	108.7 (9)
N5—C1A—C2A	103.16 (5)	C2—N2—C2A	111.80 (5)
N1—C1A—C2A	103.35 (5)	C2—N2—C3	121.90 (6)
C1B—C1A—C2A	114.47 (5)	C2A—N2—C3	116.10 (5)
O1B—C1B—N1B	124.96 (6)	C2B—N2B—C2C	121.43 (6)
O1B—C1B—C1A	118.37 (6)	C2B—N2B—H2	120.6 (7)
N1B—C1B—C1A	116.64 (5)	C2C—N2B—H2	117.9 (7)
N1B—C1C—C1D	112.28 (6)	C2D—O2D—H2D	106.6 (8)
N1B—C1C—H1C1	106.7 (7)	O3—C3—N2	110.10 (6)
C1D—C1C—H1C1	109.5 (7)	O3—C3—H3A	108.4 (7)
N1B—C1C—H1C2	109.2 (7)	N2—C3—H3A	109.4 (7)
C1D—C1C—H1C2	111.0 (7)	O3—C3—H3B	110.1 (6)
H1C1—C1C—H1C2	108.0 (9)	N2—C3—H3B	108.5 (6)
O1D—C1D—C1C	112.14 (7)	H3A—C3—H3B	110.3 (9)
O1D—C1D—H1D1	108.1 (7)	C3—O3—C4	110.35 (6)
C1C—C1D—H1D1	105.8 (7)	O3—C4—N4	110.41 (6)
O1D—C1D—H1D2	108.8 (7)	O3—C4—H4A	108.2 (6)
C1C—C1D—H1D2	110.3 (7)	N4—C4—H4A	109.9 (7)
H1D1—C1D—H1D2	111.7 (10)	O3—C4—H4B	109.1 (6)
C2—N1—C1	119.69 (6)	N4—C4—H4B	108.3 (6)
C2—N1—C1A	110.74 (5)	H4A—C4—H4B	111.0 (9)
C1—N1—C1A	114.82 (6)	C5—N4—C4	119.10 (6)
C1B—N1B—C1C	120.49 (6)	C5—N4—C2A	110.39 (5)
C1B—N1B—H1	121.0 (7)	C4—N4—C2A	114.79 (5)
C1C—N1B—H1	118.5 (7)	O5—C5—N5	126.12 (6)
C1D—O1D—H1D	105.6 (9)	O5—C5—N4	126.03 (6)
O2—C2—N2	126.07 (7)	N5—C5—N4	107.77 (5)
O2—C2—N1	125.78 (7)	C5—N5—C6	121.31 (5)
N2—C2—N1	108.02 (5)	C5—N5—C1A	111.24 (5)
N2—C2A—N4	111.00 (5)	C6—N5—C1A	115.99 (5)
N2—C2A—C2B	112.62 (5)	O6—C6—N5	110.47 (6)
N4—C2A—C2B	111.83 (5)	O6—C6—H6A	109.0 (6)
N2—C2A—C1A	103.01 (5)	N5—C6—H6A	107.9 (6)
N4—C2A—C1A	103.33 (5)	O6—C6—H6B	110.2 (6)
C2B—C2A—C1A	114.38 (5)	N5—C6—H6B	106.9 (6)
O2B—C2B—N2B	125.08 (6)	H6A—C6—H6B	112.3 (9)
O2B—C2B—C2A	119.91 (6)	C6—O6—C1	110.32 (5)
N2B—C2B—C2A	114.96 (5)	H11A—O11—H11B	104.5 (13)
N2B—C2C—C2D	112.23 (6)	H12A—O12—H12B	117 (2)
N2B—C2C—H2C1	107.7 (7)	H13A—O13—H13B	102 (2)
C2D—C2C—H2C1	110.2 (7)
N5—C1A—C1B—O1B	165.77 (6)	N1—C2—N2—C3	−159.59 (6)
N1—C1A—C1B—O1B	40.11 (8)	N4—C2A—N2—C2	−103.23 (6)
C2A—C1A—C1B—O1B	−76.07 (7)	C2B—C2A—N2—C2	130.50 (6)
N5—C1A—C1B—N1B	−16.19 (8)	C1A—C2A—N2—C2	6.77 (7)
N1—C1A—C1B—N1B	−141.85 (6)	N4—C2A—N2—C3	42.84 (7)
C2A—C1A—C1B—N1B	101.98 (6)	C2B—C2A—N2—C3	−83.43 (7)
N1B—C1C—C1D—O1D	−71.57 (8)	C1A—C2A—N2—C3	152.84 (5)
O6—C1—N1—C2	−82.18 (8)	O2B—C2B—N2B—C2C	1.93 (10)
O6—C1—N1—C1A	53.29 (8)	C2A—C2B—N2B—C2C	−175.32 (6)
N5—C1A—N1—C2	96.18 (6)	C2D—C2C—N2B—C2B	72.89 (8)
C1B—C1A—N1—C2	−136.75 (6)	C2—N2—C3—O3	90.95 (7)
C2A—C1A—N1—C2	−13.84 (7)	C2A—N2—C3—O3	−51.43 (8)
N5—C1A—N1—C1	−43.17 (7)	N2—C3—O3—C4	59.48 (8)
C1B—C1A—N1—C1	83.90 (7)	C3—O3—C4—N4	−61.09 (8)
C2A—C1A—N1—C1	−153.19 (5)	O3—C4—N4—C5	−80.44 (8)
O1B—C1B—N1B—C1C	0.71 (10)	O3—C4—N4—C2A	53.69 (8)
C1A—C1B—N1B—C1C	−177.19 (6)	N2—C2A—N4—C5	94.43 (6)
C1D—C1C—N1B—C1B	−86.80 (8)	C2B—C2A—N4—C5	−138.87 (5)
C1—N1—C2—O2	−28.05 (10)	C1A—C2A—N4—C5	−15.37 (6)
C1A—N1—C2—O2	−165.16 (7)	N2—C2A—N4—C4	−43.58 (7)
C1—N1—C2—N2	155.81 (6)	C2B—C2A—N4—C4	83.12 (7)
C1A—N1—C2—N2	18.70 (7)	C1A—C2A—N4—C4	−153.38 (5)
N5—C1A—C2A—N2	−111.63 (5)	C4—N4—C5—O5	−25.79 (10)
N1—C1A—C2A—N2	4.17 (6)	C2A—N4—C5—O5	−161.75 (6)
C1B—C1A—C2A—N2	124.42 (5)	C4—N4—C5—N5	157.38 (6)
N5—C1A—C2A—N4	4.01 (6)	C2A—N4—C5—N5	21.43 (7)
N1—C1A—C2A—N4	119.81 (5)	O5—C5—N5—C6	22.69 (10)
C1B—C1A—C2A—N4	−119.94 (5)	N4—C5—N5—C6	−160.49 (6)
N5—C1A—C2A—C2B	125.81 (5)	O5—C5—N5—C1A	164.56 (6)
N1—C1A—C2A—C2B	−118.39 (5)	N4—C5—N5—C1A	−18.61 (7)
C1B—C1A—C2A—C2B	1.86 (7)	N1—C1A—N5—C5	−101.57 (6)
N2—C2A—C2B—O2B	160.42 (6)	C1B—C1A—N5—C5	133.06 (5)
N4—C2A—C2B—O2B	34.60 (8)	C2A—C1A—N5—C5	8.56 (6)
C1A—C2A—C2B—O2B	−82.42 (7)	N1—C1A—N5—C6	42.49 (7)
N2—C2A—C2B—N2B	−22.18 (8)	C1B—C1A—N5—C6	−82.87 (7)
N4—C2A—C2B—N2B	−147.99 (6)	C2A—C1A—N5—C6	152.63 (5)
C1A—C2A—C2B—N2B	94.99 (6)	C5—N5—C6—O6	88.92 (7)
N2B—C2C—C2D—O2D	59.19 (8)	C1A—N5—C6—O6	−51.27 (7)
O2—C2—N2—C2A	168.10 (7)	N5—C6—O6—C1	59.29 (7)
N1—C2—N2—C2A	−15.78 (7)	N1—C1—O6—C6	−60.69 (8)
O2—C2—N2—C3	24.29 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11B···O2B^i	0.881 (13)	1.898 (14)	2.7642 (8)	167.4 (13)
O11—H11A···O1D^ii	0.888 (15)	1.945 (15)	2.8264 (9)	171.3 (13)
N2B—H2···O2D^iii	0.857 (10)	2.035 (10)	2.8491 (8)	158.4 (9)
O2D—H2D···O1B	0.853 (14)	1.951 (14)	2.8011 (8)	174.1 (13)
O1D—H1D···O11	0.888 (15)	1.921 (15)	2.8009 (9)	170.8 (14)
N1B—H1···O5^iv	0.882 (11)	2.176 (11)	3.0264 (8)	162.0 (10)
O12—H12A···O2	0.903 (17)	1.948 (17)	2.8127 (18)	159.8 (17)
O12—H12B···O1B^v	0.95 (3)	2.04 (3)	2.9712 (17)	168 (3)
O13—H13A···O2	1.01 (2)	1.95 (2)	2.912 (2)	159 (2)

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