1,2-Dimethyl-4-nitro-5-morpholinoimidazole and its hydrate: a case of a centrosymmetric–noncentrosymmetric ambiguity

The compound studied is 1,2-dimethyl-4-nitro-5-morpholino­imidazole (1) in its anhydrous (1) and hydrated [(1)·H₂O] crystal forms. In spite of the strong electron-withdrawing effect of the nitro group, the unsubstituted N atom of the imidazole moiety retains its basic character and acts as an acceptor for intermolecular hydrogen bonds: either weak C—H...N bonds in (1) or strong O—H...N bonds, with the water molecules, in (1)·H₂O. The packing in (1) is determined by weak C—H...N and C—H...O hydrogen bonds, van der Waals interactions and the stacking of imidazole fragments. The crystal structure of (1)·H₂O is determined by strong O—H(water)...N3(imidazole) and O—H(water)...O(water) hydrogen bonds. This structure consists of a centrosymmetric `matrix' of imidazole derivative molecules and locally noncentrosymmetric arrays of hydrogen-bonded water molecules. Each of these arrays is strictly homodromic, i.e. it runs only in one direction: ...H—O...H—O...H—O... or ...O—H...O—H...O—H.... These homodromic domains are statistically distributed within the crystal.

Computing details

Data collection: KUMA KM4 software (Kuma Diffraction, 1991) for (1); CrysAlis CCD v.158 for (2), (3). Cell refinement: KUMA KM4 software (Kuma Diffraction, 1991) for (1); CrysAlis CCD v.158 for (2), (3). Data reduction: KUMA KM4 software (Kuma Diffraction, 1991) for (1); CrysAlis RED v.158 for (2), (3). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

Figures

(1) 1,2-Dimethyl-4-nitro-5-morpholine-imidazole

Crystal data

C9H14N4O3	F(000) = 240
Mr = 226.24	Dx = 1.329 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
a = 8.589 (2) Å	Cell parameters from 25 reflections
b = 6.675 (1) Å	θ = 8–15°
c = 10.657 (2) Å	µ = 0.10 mm^−1
β = 112.23 (3)°	T = 293 K
V = 565.57 (19) Å^3	Block, colourless
Z = 2	0.3 × 0.2 × 0.15 mm

Data collection

KM4 four-circle diffractometer	Rint = 0.033
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 3.7°
Graphite monochromator	h = 0→10
ω/2Θ scans	k = 0→7
1140 measured reflections	l = −12→11
1068 independent reflections	3 standard reflections every 100 reflections
908 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.012P)^2 + 0.250P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1068 reflections	Δρmax = 0.19 e Å^−3
94 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.68 (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	Occ. (<1)
N1	0.1556 (2)	0.2500	−0.11610 (19)	0.0537 (6)
C11	0.2450 (4)	0.2500	−0.2081 (3)	0.0860 (11)
H11A	0.1652	0.2500	−0.3000	0.112*	0.50
H11B	0.3143	0.1326	−0.1925	0.112*	0.50
H11D	0.3640	0.2500	−0.1566	0.112*	0.50
H11E	0.2149	0.3674	−0.2642	0.112*	0.50
C2	0.2256 (3)	0.2500	0.0218 (2)	0.0511 (6)
C21	0.4092 (3)	0.2500	0.1001 (3)	0.0708 (8)
H21A	0.4674	0.2500	0.0389	0.092*	0.50
H21B	0.4397	0.1326	0.1562	0.092*	0.50
H21D	0.4305	0.2500	0.1953	0.092*	0.50
H21E	0.4582	0.3674	0.0780	0.092*	0.50
N3	0.1108 (2)	0.2500	0.07445 (19)	0.0515 (6)
C4	−0.0374 (3)	0.2500	−0.0341 (2)	0.0472 (6)
N4	−0.1904 (3)	0.2500	−0.0126 (3)	0.0627 (6)
O41	−0.3226 (2)	0.2500	−0.1123 (2)	0.0810 (7)
O42	−0.1848 (3)	0.2500	0.1038 (2)	0.0970 (8)
C5	−0.0162 (3)	0.2500	−0.1553 (2)	0.0487 (6)
N51	−0.1166 (3)	0.2500	−0.2927 (2)	0.0592 (6)
C52	−0.2144 (3)	0.0691 (4)	−0.3464 (2)	0.0842 (7)
H52A	−0.3076	0.0609	−0.3163	0.101*
H52B	−0.1442	−0.0485	−0.3139	0.101*
C53	−0.2796 (3)	0.0767 (5)	−0.4980 (2)	0.1037 (9)
H53A	−0.1854	0.0732	−0.5272	0.124*
H53B	−0.3484	−0.0407	−0.5346	0.124*
O54	−0.3755 (3)	0.2500	−0.5500 (2)	0.1033 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0429 (11)	0.0695 (15)	0.0462 (11)	0.000	0.0139 (9)	0.000
C11	0.0579 (17)	0.143 (3)	0.0606 (17)	0.000	0.0269 (14)	0.000
C2	0.0447 (13)	0.0538 (15)	0.0479 (14)	0.000	0.0099 (11)	0.000
C21	0.0491 (15)	0.087 (2)	0.0630 (17)	0.000	0.0059 (12)	0.000
N3	0.0516 (11)	0.0516 (13)	0.0461 (11)	0.000	0.0125 (9)	0.000
C4	0.0416 (12)	0.0459 (14)	0.0522 (14)	0.000	0.0156 (10)	0.000
N4	0.0524 (13)	0.0628 (15)	0.0746 (16)	0.000	0.0259 (12)	0.000
O41	0.0442 (10)	0.0976 (17)	0.0963 (15)	0.000	0.0209 (10)	0.000
O42	0.0847 (16)	0.141 (2)	0.0825 (16)	0.000	0.0515 (13)	0.000
C5	0.0427 (12)	0.0488 (14)	0.0474 (13)	0.000	0.0089 (10)	0.000
N51	0.0525 (12)	0.0655 (15)	0.0453 (11)	0.000	0.0023 (9)	0.000
C52	0.0902 (15)	0.0723 (15)	0.0619 (12)	−0.0086 (12)	−0.0030 (10)	−0.0079 (11)
C53	0.1044 (18)	0.110 (2)	0.0677 (14)	−0.0025 (17)	0.0001 (12)	−0.0247 (15)
O54	0.0957 (17)	0.124 (2)	0.0541 (13)	0.000	−0.0122 (11)	0.000

Geometric parameters (Å, º)

N1—C2	1.361 (3)	C4—C5	1.371 (3)
N1—C5	1.373 (3)	C4—N4	1.417 (3)
N1—C11	1.456 (3)	N4—O42	1.222 (3)
C11—H11A	0.9600	N4—O41	1.227 (3)
C11—H11B	0.9600	C5—N51	1.390 (3)
C11—H11D	0.9600	N51—C52	1.459 (2)
C11—H11E	0.9600	N51—C52^i	1.459 (2)
C2—N3	1.306 (3)	C52—C53	1.497 (3)
C2—C21	1.479 (3)	C52—H52A	0.9700
C21—H21A	0.9600	C52—H52B	0.9700
C21—H21B	0.9600	C53—O54	1.407 (3)
C21—H21D	0.9600	C53—H53A	0.9700
C21—H21E	0.9600	C53—H53B	0.9700
N3—C4	1.358 (3)	O54—C53^i	1.407 (3)
C2—N1—C5	108.3 (2)	C2—N3—C4	104.52 (19)
C2—N1—C11	126.6 (2)	N3—C4—C5	112.8 (2)
C5—N1—C11	125.1 (2)	N3—C4—N4	119.3 (2)
N1—C11—H11A	109.4	C5—C4—N4	127.9 (2)
N1—C11—H11B	109.5	O42—N4—O41	123.2 (2)
H11A—C11—H11B	109.5	O42—N4—C4	118.8 (2)
N1—C11—H11D	109.5	O41—N4—C4	118.1 (2)
H11A—C11—H11D	141.1	C4—C5—N1	102.92 (19)
H11B—C11—H11D	56.3	C4—C5—N51	137.9 (2)
N1—C11—H11E	109.5	N1—C5—N51	119.2 (2)
H11A—C11—H11E	56.3	C5—N51—C52	116.69 (13)
H11B—C11—H11E	141.1	C5—N51—C52^i	116.69 (13)
H11D—C11—H11E	109.5	C52—N51—C52^i	111.7 (2)
N3—C2—N1	111.5 (2)	N51—C52—C53	108.7 (2)
N3—C2—C21	125.1 (2)	N51—C52—H52A	110.0
N1—C2—C21	123.4 (2)	C53—C52—H52A	110.0
C2—C21—H21A	109.5	N51—C52—H52B	110.0
C2—C21—H21B	109.4	C53—C52—H52B	110.0
H21A—C21—H21B	109.5	H52A—C52—H52B	108.3
C2—C21—H21D	109.4	O54—C53—C52	112.1 (2)
H21A—C21—H21D	141.1	O54—C53—H53A	109.2
H21B—C21—H21D	56.3	C52—C53—H53A	109.2
C2—C21—H21E	109.5	O54—C53—H53B	109.2
H21A—C21—H21E	56.3	C52—C53—H53B	109.2
H21B—C21—H21E	141.1	H53A—C53—H53B	107.9
H21D—C21—H21E	109.5	C53^i—O54—C53	110.6 (3)
C5—N1—C2—N3	0.0	N3—C4—C5—N51	180.0
C11—N1—C2—N3	180.0	N4—C4—C5—N51	0.0
C5—N1—C2—C21	180.0	C2—N1—C5—C4	0.0
C11—N1—C2—C21	0.0	C11—N1—C5—C4	180.0
N1—C2—N3—C4	0.0	C2—N1—C5—N51	180.0
C21—C2—N3—C4	180.0	C11—N1—C5—N51	0.0
C2—N3—C4—C5	0.0	C4—C5—N51—C52	−67.89 (18)
C2—N3—C4—N4	180.0	N1—C5—N51—C52	112.11 (18)
N3—C4—N4—O42	0.0	C4—C5—N51—C52^i	67.89 (18)
C5—C4—N4—O42	180.0	N1—C5—N51—C52^i	−112.11 (18)
N3—C4—N4—O41	180.0	C5—N51—C52—C53	−166.3 (2)
C5—C4—N4—O41	0.0	C52^i—N51—C52—C53	55.8 (3)
N3—C4—C5—N1	0.0	N51—C52—C53—O54	−56.7 (3)
N4—C4—C5—N1	180.0	C52—C53—O54—C53^i	58.4 (4)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21D···O54^ii	0.96	2.59	3.480 (4)	154
C52—H52B···N3^iii	0.97	2.80	3.432 (3)	123
C11—H11D···O41^iv	0.96	2.55	3.460 (3)	158
C21—H21A···O41^iv	0.96	2.84	3.791 (4)	173
C21—H21A···O42^iv	0.96	2.80	3.473 (4)	128

Symmetry codes: (ii) x+1, y, z+1; (iii) −x, −y, −z; (iv) x+1, y, z.

(2) 1,2-Dimethyl-4-nitro-5-morpholine-imidazole hydrate

Crystal data

C9H14N4O3·H2O	Z = 4
Mr = 244.26	F(000) = 520
Triclinic, P1	Dx = 1.437 Mg m^−3
a = 10.1972 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2908 (9) Å	Cell parameters from 2644 reflections
c = 11.1812 (12) Å	θ = 5–20°
α = 95.319 (8)°	µ = 0.11 mm^−1
β = 92.235 (9)°	T = 293 K
γ = 90.777 (8)°	Prism, colourless
V = 1167.2 (2) Å^3	0.3 × 0.15 × 0.1 mm

Data collection

KUMA KM4CCD κ-craddle diffractometer	4180 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.011
Graphite monochromator	θmax = 27.0°, θmin = 3.5°
ω–scan	h = −12→12
6520 measured reflections	k = −13→13
4860 independent reflections	l = 0→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0601P)^2 + 0.1765P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.014
4860 reflections	Δρmax = 0.18 e Å^−3
444 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.150 (7)

Special details

Experimental. 2 standard frames collected every 50 frames, no decay in intensity observed.

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)
N1A	0.55911 (11)	0.79282 (10)	1.02008 (9)	0.0386 (2)
C11A	0.53571 (19)	0.69762 (15)	1.10609 (15)	0.0534 (4)
H11A	0.622 (2)	0.6781 (19)	1.1412 (18)	0.070 (5)*
H11B	0.497 (2)	0.624 (2)	1.0637 (19)	0.075 (6)*
H11C	0.477 (2)	0.727 (2)	1.169 (2)	0.075 (6)*
C2A	0.50083 (13)	0.78885 (12)	0.90597 (12)	0.0415 (3)
C21A	0.39048 (18)	0.69759 (17)	0.86410 (18)	0.0584 (4)
H21A	0.316 (3)	0.719 (3)	0.905 (2)	0.097 (8)*
H21B	0.378 (2)	0.705 (2)	0.774 (2)	0.100 (8)*
H21C	0.412 (2)	0.609 (2)	0.8796 (18)	0.075 (6)*
N3A	0.55427 (12)	0.87336 (11)	0.84208 (10)	0.0440 (3)
C4A	0.65022 (13)	0.93583 (12)	0.91746 (11)	0.0395 (3)
N4A	0.71806 (13)	1.04363 (12)	0.88120 (11)	0.0491 (3)
O41A	0.69052 (15)	1.07925 (16)	0.78057 (12)	0.0831 (4)
O42A	0.80200 (12)	1.10086 (11)	0.95088 (11)	0.0616 (3)
C5A	0.65669 (12)	0.88711 (11)	1.02962 (10)	0.0344 (3)
N51A	0.73443 (10)	0.91833 (11)	1.13024 (9)	0.0404 (3)
C52A	0.68560 (13)	0.91842 (14)	1.25208 (11)	0.0407 (3)
H52A	0.7077 (17)	0.8365 (17)	1.2855 (15)	0.054 (4)*
H52B	0.5908 (17)	0.9323 (16)	1.2479 (14)	0.049 (4)*
C53A	0.75180 (14)	1.02905 (15)	1.33071 (13)	0.0447 (3)
H53A	0.7279 (17)	1.1108 (18)	1.3001 (16)	0.057 (5)*
H53B	0.7279 (17)	1.0256 (16)	1.4147 (16)	0.054 (4)*
O54A	0.89125 (10)	1.02003 (10)	1.33088 (9)	0.0490 (3)
C55A	0.93616 (16)	1.02495 (17)	1.21218 (14)	0.0516 (4)
H55A	0.9163 (17)	1.1073 (18)	1.1792 (16)	0.056 (5)*
H55B	1.0317 (19)	1.0159 (17)	1.2196 (15)	0.057 (5)*
C56A	0.87740 (13)	0.91522 (14)	1.12684 (13)	0.0436 (3)
H56A	0.9059 (16)	0.9207 (16)	1.0443 (16)	0.050 (4)*
H56B	0.9090 (17)	0.8298 (18)	1.1521 (16)	0.056 (5)*
N1B	−0.03131 (10)	0.70881 (9)	0.56171 (9)	0.0341 (2)
C11B	−0.13654 (14)	0.80020 (14)	0.54053 (14)	0.0455 (3)
H11D	−0.2092 (19)	0.7553 (19)	0.4941 (17)	0.065 (5)*
H11E	−0.100 (2)	0.866 (2)	0.4930 (19)	0.076 (6)*
H11F	−0.168 (2)	0.837 (2)	0.6192 (19)	0.073 (6)*
C2B	0.08689 (12)	0.70602 (12)	0.50615 (11)	0.0366 (3)
C21B	0.11580 (17)	0.78342 (16)	0.40435 (14)	0.0496 (3)
H21D	0.208 (2)	0.775 (2)	0.3896 (19)	0.079 (6)*
H21E	0.098 (2)	0.872 (2)	0.4239 (18)	0.078 (6)*
H21F	0.062 (2)	0.751 (2)	0.336 (2)	0.084 (6)*
N3B	0.16923 (10)	0.62771 (10)	0.55401 (10)	0.0391 (2)
C4B	0.10197 (12)	0.57708 (11)	0.64345 (11)	0.0367 (3)
N4B	0.15675 (12)	0.47571 (11)	0.70379 (11)	0.0451 (3)
O41B	0.26485 (12)	0.43397 (12)	0.67332 (12)	0.0669 (3)
O42B	0.09418 (13)	0.43057 (11)	0.78366 (11)	0.0635 (3)
C5B	−0.02392 (12)	0.62639 (11)	0.65200 (10)	0.0335 (3)
N51B	−0.12245 (11)	0.60482 (12)	0.72637 (9)	0.0420 (3)
C52B	−0.10251 (17)	0.62879 (17)	0.85694 (12)	0.0509 (3)
H52C	−0.0092 (19)	0.6249 (17)	0.8783 (16)	0.058 (5)*
H52D	−0.1319 (18)	0.7204 (19)	0.8828 (17)	0.063 (5)*
C53B	−0.18166 (19)	0.5307 (2)	0.91691 (15)	0.0632 (4)
H53C	−0.147 (2)	0.441 (2)	0.8951 (18)	0.069 (5)*
H53D	−0.1779 (19)	0.5526 (19)	1.0010 (18)	0.069 (5)*
O54B	−0.31690 (12)	0.53279 (12)	0.87956 (10)	0.0607 (3)
C55B	−0.33145 (16)	0.49961 (17)	0.75223 (14)	0.0531 (4)
H55C	−0.2966 (18)	0.4083 (19)	0.7300 (16)	0.059 (5)*
H55D	−0.4280 (19)	0.5023 (17)	0.7321 (16)	0.059 (5)*
C56B	−0.26126 (13)	0.59865 (15)	0.68533 (12)	0.0439 (3)
H56C	−0.3030 (17)	0.6883 (18)	0.7046 (15)	0.055 (4)*
H56D	−0.2655 (17)	0.5746 (17)	0.5992 (17)	0.057 (5)*
O1W	0.54998 (15)	0.89126 (18)	0.55858 (16)	0.0699 (4)
H1WA	0.555 (3)	0.905 (3)	0.634 (3)	0.127 (11)*
H1WB	0.509 (6)	0.825 (7)	0.525 (5)	0.11 (2)*	0.50
H1WC	0.507 (7)	0.936 (6)	0.518 (6)	0.12 (2)*	0.50
O2W	0.45280 (17)	0.6293 (2)	0.52183 (18)	0.0854 (5)
H2WA	0.375 (3)	0.626 (2)	0.532 (2)	0.088 (7)*
H2WB	0.489 (7)	0.697 (8)	0.528 (6)	0.11 (2)*	0.50
H2WC	0.496 (9)	0.572 (7)	0.499 (8)	0.15 (3)*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0430 (6)	0.0319 (5)	0.0409 (5)	0.0001 (4)	−0.0035 (4)	0.0056 (4)
C11A	0.0658 (10)	0.0409 (7)	0.0547 (9)	−0.0101 (7)	−0.0033 (8)	0.0150 (6)
C2A	0.0441 (7)	0.0369 (6)	0.0422 (7)	0.0078 (5)	−0.0059 (5)	−0.0003 (5)
C21A	0.0549 (10)	0.0488 (9)	0.0681 (11)	−0.0007 (7)	−0.0167 (8)	−0.0037 (7)
N3A	0.0497 (6)	0.0455 (6)	0.0364 (5)	0.0105 (5)	−0.0036 (5)	0.0024 (4)
C4A	0.0435 (7)	0.0407 (6)	0.0351 (6)	0.0061 (5)	0.0038 (5)	0.0063 (5)
N4A	0.0526 (7)	0.0531 (7)	0.0441 (6)	0.0033 (5)	0.0114 (5)	0.0144 (5)
O41A	0.0952 (10)	0.1023 (10)	0.0586 (7)	−0.0136 (8)	0.0032 (7)	0.0466 (7)
O42A	0.0643 (7)	0.0578 (6)	0.0641 (7)	−0.0130 (5)	0.0088 (5)	0.0122 (5)
C5A	0.0362 (6)	0.0327 (5)	0.0344 (6)	0.0051 (5)	0.0013 (5)	0.0033 (4)
N51A	0.0355 (5)	0.0536 (6)	0.0321 (5)	−0.0003 (5)	0.0004 (4)	0.0035 (4)
C52A	0.0377 (7)	0.0516 (7)	0.0334 (6)	0.0012 (5)	0.0007 (5)	0.0083 (5)
C53A	0.0438 (7)	0.0508 (8)	0.0391 (7)	0.0075 (6)	0.0004 (5)	0.0012 (6)
O54A	0.0421 (5)	0.0602 (6)	0.0428 (5)	−0.0010 (4)	−0.0044 (4)	−0.0023 (4)
C55A	0.0416 (8)	0.0618 (9)	0.0502 (8)	−0.0084 (7)	0.0019 (6)	−0.0002 (7)
C56A	0.0363 (7)	0.0508 (7)	0.0433 (7)	0.0020 (5)	0.0037 (5)	0.0004 (6)
N1B	0.0329 (5)	0.0336 (5)	0.0359 (5)	0.0039 (4)	−0.0008 (4)	0.0046 (4)
C11B	0.0404 (7)	0.0452 (7)	0.0523 (8)	0.0117 (6)	−0.0019 (6)	0.0120 (6)
C2B	0.0366 (6)	0.0351 (6)	0.0375 (6)	0.0007 (5)	0.0011 (5)	0.0003 (5)
C21B	0.0563 (9)	0.0498 (8)	0.0441 (7)	0.0011 (7)	0.0076 (7)	0.0093 (6)
N3B	0.0350 (5)	0.0365 (5)	0.0455 (6)	0.0033 (4)	0.0016 (4)	0.0020 (4)
C4B	0.0352 (6)	0.0325 (6)	0.0421 (6)	0.0031 (5)	−0.0060 (5)	0.0040 (5)
N4B	0.0469 (6)	0.0362 (5)	0.0516 (6)	0.0034 (5)	−0.0122 (5)	0.0060 (5)
O41B	0.0540 (7)	0.0574 (6)	0.0905 (9)	0.0238 (5)	−0.0062 (6)	0.0141 (6)
O42B	0.0746 (8)	0.0575 (6)	0.0616 (7)	0.0059 (6)	−0.0064 (6)	0.0251 (5)
C5B	0.0344 (6)	0.0321 (5)	0.0333 (5)	−0.0007 (4)	−0.0039 (4)	0.0014 (4)
N51B	0.0374 (6)	0.0562 (7)	0.0323 (5)	−0.0022 (5)	−0.0009 (4)	0.0055 (5)
C52B	0.0549 (9)	0.0632 (9)	0.0335 (7)	−0.0013 (7)	−0.0027 (6)	0.0007 (6)
C53B	0.0697 (11)	0.0830 (12)	0.0385 (8)	−0.0002 (9)	0.0034 (7)	0.0142 (8)
O54B	0.0595 (7)	0.0786 (8)	0.0456 (6)	−0.0050 (6)	0.0161 (5)	0.0100 (5)
C55B	0.0475 (8)	0.0638 (10)	0.0481 (8)	−0.0071 (7)	0.0091 (6)	0.0040 (7)
C56B	0.0354 (7)	0.0583 (8)	0.0380 (7)	−0.0004 (6)	0.0023 (5)	0.0036 (6)
O1W	0.0681 (9)	0.0772 (9)	0.0643 (9)	0.0135 (7)	0.0025 (7)	0.0043 (7)
O2W	0.0430 (8)	0.0921 (12)	0.1174 (13)	0.0006 (8)	0.0050 (8)	−0.0105 (10)

Geometric parameters (Å, º)

N1A—C5A	1.3745 (16)	C11B—H11D	0.97 (2)
N1A—C2A	1.3832 (16)	C11B—H11E	0.98 (2)
N1A—C11A	1.4587 (17)	C11B—H11F	0.99 (2)
C11A—H11A	0.98 (2)	C2B—N3B	1.3054 (16)
C11A—H11B	0.93 (2)	C2B—C21B	1.4848 (19)
C11A—H11C	0.97 (2)	C21B—H21D	0.96 (2)
C2A—N3A	1.3024 (18)	C21B—H21E	0.94 (2)
C2A—C21A	1.489 (2)	C21B—H21F	0.96 (2)
C21A—H21A	0.92 (3)	N3B—C4B	1.3720 (17)
C21A—H21B	1.02 (3)	C4B—C5B	1.3902 (17)
C21A—H21C	0.97 (2)	C4B—N4B	1.4044 (16)
N3A—C4A	1.3780 (17)	N4B—O41B	1.2372 (17)
C4A—C5A	1.3927 (16)	N4B—O42B	1.2384 (17)
C4A—N4A	1.3994 (18)	C5B—N51B	1.3578 (16)
N4A—O41A	1.2385 (17)	N51B—C52B	1.4636 (17)
N4A—O42A	1.2392 (17)	N51B—C56B	1.4696 (17)
C5A—N51A	1.3615 (16)	C52B—C53B	1.505 (2)
N51A—C56A	1.4605 (17)	C52B—H52C	0.974 (19)
N51A—C52A	1.4686 (16)	C52B—H52D	1.01 (2)
C52A—C53A	1.507 (2)	C53B—O54B	1.426 (2)
C52A—H52A	0.979 (17)	C53B—H53C	1.01 (2)
C52A—H52B	0.979 (17)	C53B—H53D	0.95 (2)
C53A—O54A	1.4262 (17)	O54B—C55B	1.4344 (19)
C53A—H53A	0.968 (19)	C55B—C56B	1.508 (2)
C53A—H53B	0.983 (18)	C55B—H55C	1.021 (19)
O54A—C55A	1.4258 (18)	C55B—H55D	1.003 (19)
C55A—C56A	1.511 (2)	C56B—H56C	1.029 (19)
C55A—H55A	0.976 (18)	C56B—H56D	0.972 (18)
C55A—H55B	0.981 (19)	O1W—H1WA	0.84 (4)
C56A—H56A	0.985 (17)	O1W—H1WB	0.85 (7)
C56A—H56B	1.001 (18)	O1W—H1WC	0.80 (6)
N1B—C2B	1.3767 (16)	O2W—H2WA	0.80 (3)
N1B—C5B	1.3780 (15)	O2W—H2WB	0.78 (8)
N1B—C11B	1.4631 (16)	O2W—H2WC	0.77 (9)
C5A—N1A—C2A	108.13 (10)	N1B—C11B—H11D	110.2 (11)
C5A—N1A—C11A	126.13 (11)	N1B—C11B—H11E	106.6 (12)
C2A—N1A—C11A	124.92 (12)	H11D—C11B—H11E	108.7 (16)
N1A—C11A—H11A	106.3 (12)	N1B—C11B—H11F	108.8 (11)
N1A—C11A—H11B	107.6 (13)	H11D—C11B—H11F	109.4 (16)
H11A—C11A—H11B	111.4 (17)	H11E—C11B—H11F	113.0 (17)
N1A—C11A—H11C	114.1 (12)	N3B—C2B—N1B	111.77 (11)
H11A—C11A—H11C	110.4 (17)	N3B—C2B—C21B	124.67 (12)
H11B—C11A—H11C	107.2 (18)	N1B—C2B—C21B	123.56 (12)
N3A—C2A—N1A	111.84 (12)	C2B—C21B—H21D	107.5 (13)
N3A—C2A—C21A	125.33 (13)	C2B—C21B—H21E	110.8 (13)
N1A—C2A—C21A	122.84 (13)	H21D—C21B—H21E	108.6 (18)
C2A—C21A—H21A	110.6 (16)	C2B—C21B—H21F	108.8 (13)
C2A—C21A—H21B	105.5 (14)	H21D—C21B—H21F	112.1 (18)
H21A—C21A—H21B	113 (2)	H21E—C21B—H21F	109.1 (18)
C2A—C21A—H21C	110.6 (12)	C2B—N3B—C4B	104.87 (10)
H21A—C21A—H21C	107 (2)	N3B—C4B—C5B	112.10 (10)
H21B—C21A—H21C	110.8 (19)	N3B—C4B—N4B	119.71 (12)
C2A—N3A—C4A	104.78 (11)	C5B—C4B—N4B	127.73 (12)
N3A—C4A—C5A	112.03 (11)	O41B—N4B—O42B	122.84 (12)
N3A—C4A—N4A	119.78 (11)	O41B—N4B—C4B	118.35 (13)
C5A—C4A—N4A	127.85 (12)	O42B—N4B—C4B	118.80 (12)
O41A—N4A—O42A	122.39 (13)	N51B—C5B—N1B	124.66 (11)
O41A—N4A—C4A	118.41 (13)	N51B—C5B—C4B	132.20 (11)
O42A—N4A—C4A	119.19 (12)	N1B—C5B—C4B	103.14 (10)
N51A—C5A—N1A	124.30 (11)	C5B—N51B—C52B	120.90 (11)
N51A—C5A—C4A	132.48 (12)	C5B—N51B—C56B	122.53 (10)
N1A—C5A—C4A	103.22 (10)	C52B—N51B—C56B	113.71 (11)
C5A—N51A—C56A	121.48 (11)	N51B—C52B—C53B	109.44 (13)
C5A—N51A—C52A	122.68 (11)	N51B—C52B—H52C	109.4 (11)
C56A—N51A—C52A	113.41 (10)	C53B—C52B—H52C	111.9 (10)
N51A—C52A—C53A	108.64 (11)	N51B—C52B—H52D	108.6 (10)
N51A—C52A—H52A	110.0 (10)	C53B—C52B—H52D	110.1 (11)
C53A—C52A—H52A	108.3 (10)	H52C—C52B—H52D	107.3 (15)
N51A—C52A—H52B	108.3 (10)	O54B—C53B—C52B	111.18 (14)
C53A—C52A—H52B	109.4 (10)	O54B—C53B—H53C	109.0 (11)
H52A—C52A—H52B	112.2 (14)	C52B—C53B—H53C	109.1 (12)
O54A—C53A—C52A	111.66 (11)	O54B—C53B—H53D	106.3 (12)
O54A—C53A—H53A	108.0 (11)	C52B—C53B—H53D	109.6 (12)
C52A—C53A—H53A	108.9 (11)	H53C—C53B—H53D	111.6 (16)
O54A—C53A—H53B	106.0 (10)	C53B—O54B—C55B	109.89 (12)
C52A—C53A—H53B	110.2 (10)	O54B—C55B—C56B	110.64 (13)
H53A—C53A—H53B	112.1 (15)	O54B—C55B—H55C	110.3 (10)
C55A—O54A—C53A	110.30 (11)	C56B—C55B—H55C	110.4 (10)
O54A—C55A—C56A	111.63 (12)	O54B—C55B—H55D	105.9 (10)
O54A—C55A—H55A	112.7 (10)	C56B—C55B—H55D	109.1 (10)
C56A—C55A—H55A	108.2 (10)	H55C—C55B—H55D	110.4 (15)
O54A—C55A—H55B	105.3 (10)	N51B—C56B—C55B	108.52 (12)
C56A—C55A—H55B	109.9 (10)	N51B—C56B—H56C	109.6 (10)
H55A—C55A—H55B	109.1 (15)	C55B—C56B—H56C	108.7 (9)
N51A—C56A—C55A	109.39 (12)	N51B—C56B—H56D	108.1 (10)
N51A—C56A—H56A	110.6 (10)	C55B—C56B—H56D	111.6 (10)
C55A—C56A—H56A	111.5 (10)	H56C—C56B—H56D	110.2 (14)
N51A—C56A—H56B	109.4 (10)	H1WA—O1W—H1WB	121 (4)
C55A—C56A—H56B	109.2 (10)	H1WA—O1W—H1WC	122 (5)
H56A—C56A—H56B	106.6 (14)	H1WB—O1W—H1WC	89 (5)
C2B—N1B—C5B	108.11 (10)	H2WA—O2W—H2WB	119 (5)
C2B—N1B—C11B	124.83 (11)	H2WA—O2W—H2WC	127 (6)
C5B—N1B—C11B	126.33 (11)	H2WB—O2W—H2WC	114 (7)
C5A—N1A—C2A—N3A	0.16 (15)	C5B—N1B—C2B—N3B	0.14 (14)
C11A—N1A—C2A—N3A	−169.98 (14)	C11B—N1B—C2B—N3B	170.89 (12)
C5A—N1A—C2A—C21A	−179.89 (13)	C5B—N1B—C2B—C21B	−179.76 (12)
C11A—N1A—C2A—C21A	10.0 (2)	C11B—N1B—C2B—C21B	−9.02 (19)
N1A—C2A—N3A—C4A	−0.58 (15)	N1B—C2B—N3B—C4B	0.38 (14)
C21A—C2A—N3A—C4A	179.48 (14)	C21B—C2B—N3B—C4B	−179.72 (13)
C2A—N3A—C4A—C5A	0.81 (15)	C2B—N3B—C4B—C5B	−0.78 (14)
C2A—N3A—C4A—N4A	−173.02 (12)	C2B—N3B—C4B—N4B	171.98 (11)
N3A—C4A—N4A—O41A	−0.8 (2)	N3B—C4B—N4B—O41B	−0.61 (18)
C5A—C4A—N4A—O41A	−173.56 (14)	C5B—C4B—N4B—O41B	170.90 (13)
N3A—C4A—N4A—O42A	178.34 (13)	N3B—C4B—N4B—O42B	−179.47 (12)
C5A—C4A—N4A—O42A	5.6 (2)	C5B—C4B—N4B—O42B	−8.0 (2)
C2A—N1A—C5A—N51A	179.64 (12)	C2B—N1B—C5B—N51B	179.74 (11)
C11A—N1A—C5A—N51A	−10.4 (2)	C11B—N1B—C5B—N51B	9.17 (19)
C2A—N1A—C5A—C4A	0.33 (13)	C2B—N1B—C5B—C4B	−0.58 (12)
C11A—N1A—C5A—C4A	170.31 (14)	C11B—N1B—C5B—C4B	−171.15 (12)
N3A—C4A—C5A—N51A	−179.94 (13)	N3B—C4B—C5B—N51B	−179.51 (12)
N4A—C4A—C5A—N51A	−6.7 (2)	N4B—C4B—C5B—N51B	8.5 (2)
N3A—C4A—C5A—N1A	−0.70 (14)	N3B—C4B—C5B—N1B	0.85 (13)
N4A—C4A—C5A—N1A	172.51 (13)	N4B—C4B—C5B—N1B	−171.19 (12)
N1A—C5A—N51A—C56A	124.70 (14)	N1B—C5B—N51B—C52B	−122.86 (14)
C4A—C5A—N51A—C56A	−56.2 (2)	C4B—C5B—N51B—C52B	57.6 (2)
N1A—C5A—N51A—C52A	−36.38 (18)	N1B—C5B—N51B—C56B	36.80 (19)
C4A—C5A—N51A—C52A	142.72 (14)	C4B—C5B—N51B—C56B	−142.78 (14)
C5A—N51A—C52A—C53A	−143.68 (12)	C5B—N51B—C52B—C53B	−146.02 (14)
C56A—N51A—C52A—C53A	53.85 (15)	C56B—N51B—C52B—C53B	52.65 (18)
N51A—C52A—C53A—O54A	−56.54 (15)	N51B—C52B—C53B—O54B	−55.38 (19)
C52A—C53A—O54A—C55A	60.32 (15)	C52B—C53B—O54B—C55B	61.12 (19)
C53A—O54A—C55A—C56A	−59.31 (16)	C53B—O54B—C55B—C56B	−62.30 (18)
C5A—N51A—C56A—C55A	143.97 (13)	C5B—N51B—C56B—C55B	145.44 (13)
C52A—N51A—C56A—C55A	−53.33 (16)	C52B—N51B—C56B—C55B	−53.57 (16)
O54A—C55A—C56A—N51A	55.17 (17)	O54B—C55B—C56B—N51B	57.32 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···N3A	0.84 (4)	2.38 (4)	3.191 (2)	162 (3)
O2W—H2WA···N3B	0.80 (3)	2.12 (3)	2.928 (2)	177 (2)
O1W—H1WC···O1W^i	0.80 (6)	2.12 (6)	2.875 (3)	157 (6)
O2W—H2WC···O2W^ii	0.77 (9)	2.14 (8)	2.849 (5)	153 (8)
C11A—H11A···O41B^iii	0.98 (2)	2.69 (2)	3.515 (2)	141.7 (15)
C52A—H52A···O41B^iii	0.979 (17)	2.879 (18)	3.8314 (18)	164.7 (13)
C56A—H56B···O42B^iii	1.001 (18)	2.838 (18)	3.7965 (19)	160.5 (13)
C11A—H11B···O54B^iv	0.93 (2)	2.56 (2)	3.253 (2)	131.2 (16)
C53B—H53D···O42B^iv	0.95 (2)	2.51 (2)	3.417 (2)	160.0 (16)
C11A—H11C···O41A^v	0.97 (2)	2.68 (2)	3.469 (3)	139.2 (16)
C21A—H21A···O42A^v	0.92 (3)	2.67 (3)	3.474 (2)	146 (2)
C52A—H52B···N3A^v	0.979 (17)	2.745 (16)	3.4702 (18)	131.3 (12)
C52A—H52B···O41A^v	0.979 (17)	2.874 (17)	3.839 (2)	169.0 (13)
C55A—H55B···O42A^vi	0.981 (19)	2.799 (18)	3.488 (2)	127.8 (13)
C11B—H11D···O41B^vii	0.97 (2)	2.61 (2)	3.441 (2)	142.9 (15)
C21B—H21F···O42B^vii	0.96 (2)	2.67 (2)	3.538 (2)	151.8 (17)
C56B—H56D···N3B^vii	0.972 (18)	2.785 (18)	3.5452 (19)	135.6 (13)
C56B—H56D···O41B^vii	0.972 (18)	3.040 (18)	3.992 (2)	166.7 (14)
C11B—H11E···O54A^viii	0.98 (2)	2.51 (2)	3.4220 (18)	153.8 (16)
C21B—H21E···O54A^viii	0.94 (2)	2.84 (2)	3.496 (2)	127.8 (16)
C21B—H21D···O41A^i	0.96 (2)	2.75 (2)	3.310 (2)	117.4 (15)
C56B—H56C···N3A^ix	1.029 (19)	2.796 (19)	3.7529 (19)	154.8 (12)

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

(3) 1,2-Dimethyl-4-nitro-5-morpholine-imidazole hydrate

Crystal data

C9H14N4O3·H2O	Z = 4
Mr = 244.26	F(000) = 520
Triclinic, P1	Dx = 1.437 Mg m^−3
a = 10.1087 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2497 (8) Å	Cell parameters from 4474 reflections
c = 10.9623 (8) Å	θ = 5–25°
α = 95.888 (6)°	µ = 0.11 mm^−1
β = 92.119 (6)°	T = 110 K
γ = 90.188 (6)°	Prism, colourless
V = 1129.02 (14) Å^3	0.3 × 0.15 × 0.1 mm

Data collection

KUMA KM4CCD κ-craddle diffractometer	4823 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 27.0°, θmin = 3.5°
ω–scan	h = −12→12
17221 measured reflections	k = −13→13
4891 independent reflections	l = 0→13

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0376P)^2 + 0.4207P] where P = (Fo^2 + 2Fc^2)/3
4891 reflections	(Δ/σ)max = 0.001
443 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

Experimental. 2 standard frames collected every 50 frames, no decay in intensity observed.

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)
N1A	0.55519 (8)	0.79240 (8)	1.02238 (8)	0.01597 (17)
C11A	0.53236 (11)	0.69921 (10)	1.11181 (10)	0.0216 (2)
H11A	0.6165 (14)	0.6760 (14)	1.1482 (13)	0.027 (3)*
H11B	0.4895 (14)	0.6230 (14)	1.0696 (13)	0.026 (3)*
H11C	0.4747 (15)	0.7354 (15)	1.1756 (14)	0.032 (4)*
C2A	0.49632 (10)	0.78621 (9)	0.90581 (9)	0.01705 (19)
C21A	0.38525 (11)	0.69469 (11)	0.86485 (11)	0.0225 (2)
H21A	0.3056 (17)	0.7194 (17)	0.9055 (15)	0.043 (4)*
H21B	0.3719 (15)	0.6956 (16)	0.7761 (15)	0.037 (4)*
H21C	0.4072 (14)	0.6050 (15)	0.8802 (13)	0.029 (4)*
N3A	0.54991 (8)	0.86896 (8)	0.83891 (8)	0.01781 (17)
C4A	0.64719 (10)	0.93213 (10)	0.91452 (9)	0.01668 (19)
N4A	0.71501 (9)	1.03920 (9)	0.87632 (8)	0.01955 (18)
O41A	0.68691 (9)	1.07270 (9)	0.77256 (8)	0.0328 (2)
O42A	0.79948 (8)	1.09822 (8)	0.94732 (7)	0.02421 (17)
C5A	0.65380 (9)	0.88567 (9)	1.02992 (9)	0.01466 (19)
N51A	0.73274 (8)	0.91829 (8)	1.13167 (7)	0.01695 (17)
C52A	0.68481 (10)	0.91889 (10)	1.25651 (9)	0.01673 (19)
H52A	0.7084 (13)	0.8358 (13)	1.2912 (12)	0.019 (3)*
H52B	0.5898 (13)	0.9303 (13)	1.2541 (12)	0.020 (3)*
C53A	0.74987 (10)	1.03294 (10)	1.33568 (9)	0.0179 (2)
H53A	0.7226 (13)	1.1161 (13)	1.3069 (12)	0.020 (3)*
H53B	0.7265 (13)	1.0310 (13)	1.4205 (12)	0.020 (3)*
O54A	0.89116 (7)	1.02469 (7)	1.33414 (6)	0.01920 (16)
C55A	0.93525 (10)	1.02871 (11)	1.21231 (10)	0.0208 (2)
H55A	0.9114 (13)	1.1139 (14)	1.1821 (12)	0.024 (3)*
H55B	1.0309 (14)	1.0197 (13)	1.2180 (12)	0.022 (3)*
C56A	0.87705 (10)	0.91619 (10)	1.12616 (9)	0.0181 (2)
H56A	0.9024 (13)	0.9229 (13)	1.0434 (12)	0.019 (3)*
H56B	0.9105 (13)	0.8308 (14)	1.1503 (12)	0.022 (3)*
N1B	−0.03358 (8)	0.70964 (8)	0.55890 (7)	0.01422 (16)
C11B	−0.14026 (10)	0.80241 (10)	0.53932 (10)	0.0179 (2)
H11D	−0.2132 (14)	0.7590 (13)	0.4952 (12)	0.022 (3)*
H11E	−0.1050 (14)	0.8684 (14)	0.4918 (13)	0.028 (3)*
H11F	−0.1692 (13)	0.8417 (14)	0.6184 (13)	0.024 (3)*
C2B	0.08687 (9)	0.70744 (9)	0.50304 (9)	0.01509 (19)
C21B	0.11580 (11)	0.78562 (10)	0.40040 (10)	0.0194 (2)
H21D	0.2089 (16)	0.7795 (15)	0.3850 (14)	0.034 (4)*
H21E	0.0943 (14)	0.8765 (15)	0.4188 (13)	0.031 (4)*
H21F	0.0650 (15)	0.7525 (15)	0.3264 (15)	0.036 (4)*
N3B	0.17024 (8)	0.62824 (8)	0.55141 (8)	0.01610 (17)
C4B	0.10220 (9)	0.57635 (9)	0.64155 (9)	0.01566 (19)
N4B	0.15743 (8)	0.47352 (8)	0.70125 (8)	0.01801 (18)
O41B	0.26760 (8)	0.43151 (8)	0.67048 (8)	0.02572 (18)
O42B	0.09302 (8)	0.42651 (8)	0.78124 (7)	0.02442 (17)
C5B	−0.02583 (9)	0.62620 (9)	0.64964 (9)	0.01443 (18)
N51B	−0.12545 (8)	0.60380 (9)	0.72474 (7)	0.01724 (17)
C52B	−0.26532 (9)	0.60195 (10)	0.68302 (9)	0.0173 (2)
H52C	−0.3055 (12)	0.6900 (13)	0.7022 (11)	0.018 (3)*
H52D	−0.2696 (13)	0.5770 (13)	0.5943 (12)	0.020 (3)*
C53B	−0.33780 (10)	0.50305 (11)	0.75019 (9)	0.0202 (2)
H53C	−0.3041 (13)	0.4147 (13)	0.7284 (12)	0.018 (3)*
H53D	−0.4327 (13)	0.5055 (13)	0.7283 (12)	0.020 (3)*
O54B	−0.32284 (8)	0.53485 (8)	0.88041 (7)	0.02333 (17)
C55B	−0.18642 (11)	0.52805 (12)	0.91827 (10)	0.0244 (2)
H55C	−0.1535 (14)	0.4381 (14)	0.8954 (12)	0.024 (3)*
H55D	−0.1821 (14)	0.5485 (14)	1.0070 (14)	0.030 (4)*
C56B	−0.10485 (11)	0.62598 (11)	0.85819 (9)	0.0204 (2)
H56C	−0.0111 (14)	0.6180 (13)	0.8793 (12)	0.024 (3)*
H56D	−0.1349 (14)	0.7146 (15)	0.8847 (13)	0.026 (3)*
O1W	0.54842 (9)	0.88890 (11)	0.55380 (9)	0.02853 (19)
H1WA	0.5601 (19)	0.9034 (19)	0.631 (2)	0.056 (5)*
H1WB	0.513 (3)	0.816 (4)	0.536 (3)	0.041 (9)*	0.50
H1WC	0.513 (4)	0.948 (4)	0.524 (3)	0.050 (10)*	0.50
O2W	0.45302 (10)	0.62954 (13)	0.52133 (10)	0.0369 (2)
H2WA	0.3734 (19)	0.6266 (17)	0.5321 (15)	0.041 (4)*
H2WB	0.487 (4)	0.701 (5)	0.521 (4)	0.054 (11)*	0.50
H2WC	0.488 (5)	0.562 (4)	0.502 (4)	0.064 (13)*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0177 (4)	0.0137 (4)	0.0164 (4)	0.0002 (3)	−0.0016 (3)	0.0021 (3)
C11A	0.0273 (5)	0.0176 (5)	0.0205 (5)	−0.0041 (4)	−0.0018 (4)	0.0065 (4)
C2A	0.0184 (5)	0.0157 (4)	0.0164 (5)	0.0044 (4)	−0.0016 (4)	−0.0005 (4)
C21A	0.0213 (5)	0.0196 (5)	0.0254 (5)	0.0000 (4)	−0.0052 (4)	−0.0012 (4)
N3A	0.0193 (4)	0.0181 (4)	0.0157 (4)	0.0038 (3)	−0.0006 (3)	0.0004 (3)
C4A	0.0177 (5)	0.0170 (4)	0.0155 (4)	0.0025 (4)	0.0016 (4)	0.0018 (4)
N4A	0.0202 (4)	0.0218 (4)	0.0175 (4)	0.0022 (3)	0.0051 (3)	0.0046 (3)
O41A	0.0373 (5)	0.0421 (5)	0.0219 (4)	−0.0060 (4)	0.0011 (3)	0.0172 (4)
O42A	0.0240 (4)	0.0236 (4)	0.0251 (4)	−0.0050 (3)	0.0029 (3)	0.0024 (3)
C5A	0.0149 (4)	0.0135 (4)	0.0155 (4)	0.0027 (3)	0.0012 (3)	0.0005 (3)
N51A	0.0141 (4)	0.0231 (4)	0.0135 (4)	−0.0007 (3)	0.0004 (3)	0.0012 (3)
C52A	0.0156 (5)	0.0206 (5)	0.0142 (4)	0.0003 (4)	0.0008 (3)	0.0030 (4)
C53A	0.0155 (5)	0.0208 (5)	0.0170 (5)	0.0026 (4)	0.0002 (4)	0.0005 (4)
O54A	0.0153 (3)	0.0250 (4)	0.0166 (3)	−0.0002 (3)	−0.0008 (3)	−0.0005 (3)
C55A	0.0166 (5)	0.0255 (5)	0.0198 (5)	−0.0031 (4)	0.0016 (4)	−0.0005 (4)
C56A	0.0142 (5)	0.0217 (5)	0.0180 (5)	0.0010 (4)	0.0016 (4)	−0.0002 (4)
N1B	0.0131 (4)	0.0144 (4)	0.0153 (4)	0.0014 (3)	−0.0002 (3)	0.0022 (3)
C11B	0.0154 (5)	0.0176 (5)	0.0213 (5)	0.0042 (4)	−0.0005 (4)	0.0047 (4)
C2B	0.0139 (4)	0.0147 (4)	0.0162 (4)	−0.0005 (3)	0.0006 (3)	−0.0009 (3)
C21B	0.0212 (5)	0.0195 (5)	0.0180 (5)	0.0002 (4)	0.0026 (4)	0.0040 (4)
N3B	0.0153 (4)	0.0148 (4)	0.0181 (4)	0.0003 (3)	0.0007 (3)	0.0009 (3)
C4B	0.0148 (4)	0.0148 (4)	0.0172 (4)	0.0011 (3)	−0.0020 (3)	0.0016 (3)
N4B	0.0187 (4)	0.0152 (4)	0.0195 (4)	0.0007 (3)	−0.0050 (3)	0.0010 (3)
O41B	0.0197 (4)	0.0234 (4)	0.0340 (4)	0.0084 (3)	−0.0030 (3)	0.0035 (3)
O42B	0.0288 (4)	0.0233 (4)	0.0222 (4)	0.0002 (3)	−0.0024 (3)	0.0089 (3)
C5B	0.0153 (4)	0.0131 (4)	0.0143 (4)	−0.0006 (3)	−0.0022 (3)	0.0001 (3)
N51B	0.0144 (4)	0.0245 (4)	0.0130 (4)	−0.0007 (3)	0.0000 (3)	0.0026 (3)
C52B	0.0136 (4)	0.0223 (5)	0.0159 (5)	0.0010 (4)	0.0006 (3)	0.0017 (4)
C53B	0.0187 (5)	0.0242 (5)	0.0176 (5)	−0.0022 (4)	0.0029 (4)	0.0012 (4)
O54B	0.0220 (4)	0.0313 (4)	0.0171 (4)	−0.0017 (3)	0.0051 (3)	0.0030 (3)
C55B	0.0253 (5)	0.0324 (6)	0.0161 (5)	0.0002 (4)	0.0010 (4)	0.0056 (4)
C56B	0.0217 (5)	0.0254 (5)	0.0135 (5)	−0.0004 (4)	−0.0012 (4)	0.0002 (4)
O1W	0.0254 (4)	0.0347 (5)	0.0251 (5)	0.0048 (4)	0.0006 (3)	0.0010 (4)
O2W	0.0156 (4)	0.0468 (6)	0.0465 (6)	−0.0017 (4)	0.0026 (4)	−0.0043 (5)

Geometric parameters (Å, º)

N1A—C5A	1.3732 (13)	C11B—H11D	0.950 (14)
N1A—C2A	1.3849 (13)	C11B—H11E	0.970 (15)
N1A—C11A	1.4609 (13)	C11B—H11F	0.973 (14)
C11A—H11A	0.967 (15)	C2B—N3B	1.3077 (13)
C11A—H11B	0.960 (15)	C2B—C21B	1.4838 (14)
C11A—H11C	0.972 (16)	C21B—H21D	0.963 (16)
C2A—N3A	1.3057 (14)	C21B—H21E	0.960 (15)
C2A—C21A	1.4871 (15)	C21B—H21F	0.974 (16)
C21A—H21A	0.957 (18)	N3B—C4B	1.3741 (13)
C21A—H21B	0.978 (16)	C4B—C5B	1.3956 (14)
C21A—H21C	0.976 (15)	C4B—N4B	1.4034 (13)
N3A—C4A	1.3780 (14)	N4B—O41B	1.2412 (12)
C4A—C5A	1.3961 (14)	N4B—O42B	1.2458 (12)
C4A—N4A	1.4001 (14)	C5B—N51B	1.3576 (13)
N4A—O41A	1.2447 (12)	N51B—C56B	1.4642 (13)
N4A—O42A	1.2457 (13)	N51B—C52B	1.4693 (13)
C5A—N51A	1.3596 (13)	C52B—C53B	1.5149 (15)
N51A—C56A	1.4624 (13)	C52B—H52C	0.997 (13)
N51A—C52A	1.4680 (13)	C52B—H52D	0.979 (13)
C52A—C53A	1.5155 (15)	C53B—O54B	1.4334 (13)
C52A—H52A	0.994 (13)	C53B—H53C	0.979 (13)
C52A—H52B	0.968 (13)	C53B—H53D	0.981 (13)
C53A—O54A	1.4318 (12)	O54B—C55B	1.4294 (14)
C53A—H53A	0.976 (14)	C55B—C56B	1.5139 (16)
C53A—H53B	0.969 (13)	C55B—H55C	0.992 (14)
O54A—C55A	1.4280 (13)	C55B—H55D	0.973 (15)
C55A—C56A	1.5162 (15)	C56B—H56C	0.973 (14)
C55A—H55A	0.993 (14)	C56B—H56D	0.978 (15)
C55A—H55B	0.972 (14)	O1W—H1WA	0.84 (2)
C56A—H56A	0.961 (13)	O1W—H1WB	0.83 (4)
C56A—H56B	0.997 (14)	O1W—H1WC	0.80 (4)
N1B—C5B	1.3771 (13)	O2W—H2WA	0.819 (19)
N1B—C2B	1.3823 (13)	O2W—H2WB	0.81 (5)
N1B—C11B	1.4646 (13)	O2W—H2WC	0.79 (4)
C5A—N1A—C2A	107.84 (9)	N1B—C11B—H11D	110.6 (8)
C5A—N1A—C11A	126.09 (9)	N1B—C11B—H11E	107.2 (8)
C2A—N1A—C11A	125.15 (9)	H11D—C11B—H11E	109.5 (12)
N1A—C11A—H11A	109.0 (9)	N1B—C11B—H11F	109.3 (8)
N1A—C11A—H11B	108.1 (8)	H11D—C11B—H11F	109.2 (11)
H11A—C11A—H11B	110.4 (12)	H11E—C11B—H11F	111.0 (12)
N1A—C11A—H11C	111.6 (9)	N3B—C2B—N1B	111.71 (9)
H11A—C11A—H11C	109.8 (12)	N3B—C2B—C21B	124.90 (9)
H11B—C11A—H11C	107.9 (12)	N1B—C2B—C21B	123.39 (9)
N3A—C2A—N1A	112.04 (9)	C2B—C21B—H21D	108.8 (9)
N3A—C2A—C21A	125.33 (9)	C2B—C21B—H21E	112.1 (9)
N1A—C2A—C21A	122.63 (10)	H21D—C21B—H21E	108.3 (12)
C2A—C21A—H21A	111.6 (10)	C2B—C21B—H21F	110.6 (9)
C2A—C21A—H21B	107.7 (9)	H21D—C21B—H21F	109.3 (13)
H21A—C21A—H21B	110.3 (13)	H21E—C21B—H21F	107.7 (12)
C2A—C21A—H21C	111.0 (9)	C2B—N3B—C4B	105.15 (8)
H21A—C21A—H21C	108.8 (13)	N3B—C4B—C5B	111.65 (9)
H21B—C21A—H21C	107.4 (13)	N3B—C4B—N4B	119.88 (9)
C2A—N3A—C4A	104.71 (8)	C5B—C4B—N4B	127.93 (9)
N3A—C4A—C5A	111.84 (9)	O41B—N4B—O42B	122.68 (9)
N3A—C4A—N4A	119.89 (9)	O41B—N4B—C4B	118.54 (9)
C5A—C4A—N4A	127.86 (10)	O42B—N4B—C4B	118.77 (9)
O41A—N4A—O42A	122.51 (9)	N51B—C5B—N1B	124.69 (9)
O41A—N4A—C4A	118.29 (9)	N51B—C5B—C4B	131.74 (9)
O42A—N4A—C4A	119.19 (9)	N1B—C5B—C4B	103.57 (9)
N51A—C5A—N1A	124.14 (9)	C5B—N51B—C56B	120.42 (9)
N51A—C5A—C4A	132.29 (9)	C5B—N51B—C52B	122.35 (8)
N1A—C5A—C4A	103.57 (9)	C56B—N51B—C52B	113.95 (8)
C5A—N51A—C56A	121.34 (8)	N51B—C52B—C53B	108.15 (8)
C5A—N51A—C52A	122.56 (8)	N51B—C52B—H52C	110.5 (7)
C56A—N51A—C52A	113.66 (8)	C53B—C52B—H52C	109.0 (7)
N51A—C52A—C53A	108.22 (8)	N51B—C52B—H52D	108.0 (8)
N51A—C52A—H52A	110.5 (7)	C53B—C52B—H52D	111.0 (8)
C53A—C52A—H52A	109.2 (8)	H52C—C52B—H52D	110.2 (10)
N51A—C52A—H52B	109.0 (8)	O54B—C53B—C52B	110.76 (9)
C53A—C52A—H52B	109.5 (8)	O54B—C53B—H53C	109.2 (7)
H52A—C52A—H52B	110.4 (11)	C52B—C53B—H53C	110.5 (8)
O54A—C53A—C52A	111.20 (8)	O54B—C53B—H53D	107.5 (8)
O54A—C53A—H53A	108.8 (8)	C52B—C53B—H53D	109.2 (8)
C52A—C53A—H53A	110.5 (8)	H53C—C53B—H53D	109.6 (11)
O54A—C53A—H53B	106.4 (8)	C55B—O54B—C53B	109.92 (8)
C52A—C53A—H53B	110.1 (8)	O54B—C55B—C56B	110.65 (9)
H53A—C53A—H53B	109.8 (11)	O54B—C55B—H55C	109.3 (8)
C55A—O54A—C53A	110.46 (8)	C56B—C55B—H55C	109.7 (8)
O54A—C55A—C56A	111.28 (9)	O54B—C55B—H55D	106.6 (9)
O54A—C55A—H55A	110.0 (8)	C56B—C55B—H55D	110.2 (9)
C56A—C55A—H55A	110.3 (8)	H55C—C55B—H55D	110.4 (12)
O54A—C55A—H55B	105.8 (8)	N51B—C56B—C55B	109.49 (9)
C56A—C55A—H55B	109.2 (8)	N51B—C56B—H56C	109.3 (8)
H55A—C55A—H55B	110.2 (11)	C55B—C56B—H56C	111.1 (8)
N51A—C56A—C55A	109.23 (9)	N51B—C56B—H56D	107.9 (8)
N51A—C56A—H56A	109.8 (8)	C55B—C56B—H56D	109.1 (8)
C55A—C56A—H56A	110.8 (8)	H56C—C56B—H56D	110.0 (11)
N51A—C56A—H56B	109.3 (8)	H1WA—O1W—H1WB	110 (3)
C55A—C56A—H56B	110.3 (8)	H1WA—O1W—H1WC	113 (3)
H56A—C56A—H56B	107.4 (11)	H1WB—O1W—H1WC	115 (4)
C5B—N1B—C2B	107.91 (8)	H2WA—O2W—H2WB	118 (3)
C5B—N1B—C11B	126.17 (8)	H2WA—O2W—H2WC	117 (3)
C2B—N1B—C11B	125.05 (8)	H2WB—O2W—H2WC	125 (4)
C5A—N1A—C2A—N3A	−0.23 (11)	C5B—N1B—C2B—N3B	0.28 (11)
C11A—N1A—C2A—N3A	−169.82 (9)	C11B—N1B—C2B—N3B	170.12 (9)
C5A—N1A—C2A—C21A	179.75 (9)	C5B—N1B—C2B—C21B	179.98 (9)
C11A—N1A—C2A—C21A	10.16 (15)	C11B—N1B—C2B—C21B	−10.18 (15)
N1A—C2A—N3A—C4A	−0.23 (11)	N1B—C2B—N3B—C4B	0.25 (11)
C21A—C2A—N3A—C4A	179.79 (9)	C21B—C2B—N3B—C4B	−179.44 (9)
C2A—N3A—C4A—C5A	0.61 (11)	C2B—N3B—C4B—C5B	−0.70 (11)
C2A—N3A—C4A—N4A	−172.58 (9)	C2B—N3B—C4B—N4B	171.52 (8)
N3A—C4A—N4A—O41A	−1.58 (14)	N3B—C4B—N4B—O41B	−0.11 (14)
C5A—C4A—N4A—O41A	−173.57 (10)	C5B—C4B—N4B—O41B	170.71 (9)
N3A—C4A—N4A—O42A	177.52 (9)	N3B—C4B—N4B—O42B	−178.81 (8)
C5A—C4A—N4A—O42A	5.52 (15)	C5B—C4B—N4B—O42B	−7.99 (15)
C2A—N1A—C5A—N51A	179.92 (9)	C2B—N1B—C5B—N51B	179.53 (9)
C11A—N1A—C5A—N51A	−10.62 (15)	C11B—N1B—C5B—N51B	9.83 (15)
C2A—N1A—C5A—C4A	0.57 (10)	C2B—N1B—C5B—C4B	−0.66 (10)
C11A—N1A—C5A—C4A	170.03 (9)	C11B—N1B—C5B—C4B	−170.37 (9)
N3A—C4A—C5A—N51A	179.98 (10)	N3B—C4B—C5B—N51B	−179.36 (10)
N4A—C4A—C5A—N51A	−7.49 (17)	N4B—C4B—C5B—N51B	9.20 (17)
N3A—C4A—C5A—N1A	−0.74 (11)	N3B—C4B—C5B—N1B	0.85 (11)
N4A—C4A—C5A—N1A	171.78 (9)	N4B—C4B—C5B—N1B	−170.59 (9)
N1A—C5A—N51A—C56A	126.36 (10)	N1B—C5B—N51B—C56B	−123.53 (11)
C4A—C5A—N51A—C56A	−54.50 (15)	C4B—C5B—N51B—C56B	56.72 (15)
N1A—C5A—N51A—C52A	−34.79 (14)	N1B—C5B—N51B—C52B	34.77 (14)
C4A—C5A—N51A—C52A	144.35 (11)	C4B—C5B—N51B—C52B	−144.98 (11)
C5A—N51A—C52A—C53A	−142.97 (9)	C5B—N51B—C52B—C53B	146.88 (9)
C56A—N51A—C52A—C53A	54.56 (11)	C56B—N51B—C52B—C53B	−53.54 (11)
N51A—C52A—C53A—O54A	−56.98 (11)	N51B—C52B—C53B—O54B	57.39 (11)
C52A—C53A—O54A—C55A	60.93 (11)	C52B—C53B—O54B—C55B	−62.84 (11)
C53A—O54A—C55A—C56A	−59.65 (11)	C53B—O54B—C55B—C56B	61.36 (11)
C5A—N51A—C56A—C55A	143.42 (9)	C5B—N51B—C56B—C55B	−147.04 (9)
C52A—N51A—C56A—C55A	−53.87 (11)	C52B—N51B—C56B—C55B	52.94 (12)
O54A—C55A—C56A—N51A	55.16 (11)	O54B—C55B—C56B—N51B	−55.46 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···N3A	0.84 (2)	2.35 (2)	3.1523 (14)	158.6 (18)
O2W—H2WA···N3B	0.819 (19)	2.07 (2)	2.8899 (14)	176.2 (17)
O1W—H1WC···O1W^i	0.80 (4)	2.04 (4)	2.832 (2)	170 (4)
O2W—H2WC···O2W^ii	0.79 (4)	2.04 (4)	2.823 (3)	166 (5)
C11A—H11A···O41B^iii	0.967 (15)	2.612 (15)	3.4491 (17)	145.1 (11)
C52A—H52A···O41B^iii	0.994 (13)	2.824 (13)	3.7874 (15)	163.5 (10)
C56A—H56B···O42B^iii	0.997 (14)	2.815 (14)	3.7653 (15)	159.5 (10)
C11A—H11B···O54B^iv	0.960 (15)	2.447 (14)	3.2047 (16)	135.7 (11)
C55B—H55D···O42B^iv	0.973 (15)	2.447 (15)	3.3780 (16)	160.1 (12)
C11A—H11C···O41A^v	0.972 (16)	2.592 (15)	3.4088 (19)	141.7 (11)
C21A—H21A···O42A^v	0.957 (18)	2.597 (17)	3.4126 (18)	143.3 (13)
C52A—H52B···N3A^v	0.968 (13)	2.759 (13)	3.4307 (17)	127.1 (10)
C52A—H52B···O41A^v	0.968 (13)	2.801 (14)	3.7614 (15)	171.6 (10)
C55A—H55B···O42A^vi	0.972 (14)	2.735 (13)	3.4423 (17)	130.1 (10)
C11B—H11D···O41B^vii	0.950 (14)	2.570 (14)	3.3651 (18)	141.4 (11)
C21B—H21F···O42B^vii	0.974 (16)	2.590 (16)	3.4524 (18)	147.7 (12)
C52B—H52D···N3B^vii	0.979 (13)	2.726 (13)	3.4710 (17)	133.3 (10)
C52B—H52D···O41B^vii	0.979 (13)	2.896 (14)	3.8542 (15)	166.3 (10)
C11B—H11E···O54A^viii	0.970 (15)	2.473 (15)	3.3838 (16)	156.3 (12)
C21B—H21E···O54A^viii	0.960 (15)	2.749 (15)	3.4597 (16)	131.4 (11)
C21B—H21D···O41A^i	0.963 (16)	2.655 (15)	3.2414 (16)	119.6 (11)
C52B—H52C···N3A^ix	0.997 (13)	2.713 (13)	3.6346 (18)	153.8 (10)

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