A crystallographic titration of the dipeptide L-isoleucyl-L-isoleucine

The dipeptide L-Ile-L-Ile has been crystallized in four different protonation states, including as a cation, a zwitterion and an anion, as well as a dimeric cation in which two peptide molecules, linked by a strong –COO...H...OOC– hydrogen bond, share an overall positive charge of +1. This unprecedented series of crystal structures exhibits differences in hydrogen-bonding capabilities, conformational properties and molecular packing arrangements. The crystallization of L-Ile-L-Ile as an anion was achieved by slow evaporation from an NH₃(l) solution to give the first ever ammonium salt of a peptide (or amino acid).

Computing details

For all compounds, data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures

(IIc) L-Isoleucyl-L-isoleucine nitrate

Crystal data

C13.08H25N3O6	Dx = 1.238 Mg m^−3
Mr = 320.36	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3121	Cell parameters from 4175 reflections
a = 16.0682 (6) Å	θ = 2.3–26.4°
c = 11.5317 (9) Å	µ = 0.10 mm^−1
V = 2578.4 (2) Å^3	T = 105 K
Z = 6	Rod, colourless
F(000) = 1035	0.25 × 0.06 × 0.05 mm

Data collection

Siemens SMART CCD diffractometer	3401 independent reflections
Radiation source: fine-focus sealed tube	2352 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.116
Detector resolution: 8.3 pixels mm^-1	θmax = 26.4°, θmin = 2.3°
Sets of exposures each taken over 0.3° ω rotation scans	h = −20→19
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −20→18
Tmin = 0.968, Tmax = 0.995	l = −11→14
11629 measured reflections

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)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.181	w = 1/[σ^2(Fo^2) + (0.0975P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3401 reflections	Δρmax = 0.35 e Å^−3
245 parameters	Δρmin = −0.35 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −1.8 (19)

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.60602 (18)	0.28975 (17)	0.3384 (2)	0.0357 (6)
O2A	0.5928 (2)	0.08805 (17)	0.2300 (2)	0.0381 (7)
H5A	0.573 (3)	0.068 (3)	0.167 (4)	0.057*
O3A	0.70123 (18)	0.22854 (16)	0.15079 (19)	0.0342 (6)
N1A	0.5590 (2)	0.3424 (2)	0.5402 (3)	0.0415 (8)
H1A	0.6242	0.3800	0.5413	0.062*
H2A	0.5344	0.3494	0.6082	0.062*
H3A	0.5347	0.3604	0.4802	0.062*
N2A	0.6417 (2)	0.1926 (2)	0.4402 (2)	0.0296 (6)
H4A	0.6288	0.1543	0.5004	0.036*
C1A	0.5327 (3)	0.2404 (3)	0.5255 (3)	0.0334 (8)
H11A	0.5487	0.2172	0.5981	0.040*
C2A	0.4250 (3)	0.1781 (3)	0.5003 (3)	0.0353 (9)
H21A	0.4077	0.2106	0.4388	0.042*
C3A	0.4031 (3)	0.0807 (3)	0.4546 (4)	0.0557 (12)
H31A	0.4406	0.0893	0.3841	0.084*
H32A	0.3344	0.0421	0.4369	0.084*
H33A	0.4202	0.0478	0.5135	0.084*
C4A	0.3660 (3)	0.1688 (3)	0.6095 (3)	0.0372 (9)
H41A	0.3791	0.1323	0.6688	0.045*
H42A	0.3881	0.2338	0.6410	0.045*
C5A	0.2591 (3)	0.1199 (3)	0.5903 (4)	0.0517 (11)
H51A	0.2276	0.1222	0.6620	0.078*
H52A	0.2350	0.0528	0.5681	0.078*
H53A	0.2453	0.1530	0.5284	0.078*
C6A	0.5964 (2)	0.2417 (3)	0.4274 (3)	0.0289 (8)
C7A	0.7130 (2)	0.2015 (3)	0.3549 (3)	0.0300 (8)
H71A	0.7654	0.2703	0.3524	0.036*
C8A	0.7570 (3)	0.1402 (3)	0.3898 (3)	0.0336 (8)
H81A	0.7038	0.0730	0.4041	0.040*
C9A	0.8210 (3)	0.1384 (3)	0.2911 (3)	0.0423 (10)
H91A	0.7809	0.1043	0.2241	0.063*
H92A	0.8547	0.1052	0.3179	0.063*
H93A	0.8681	0.2044	0.2688	0.063*
C10A	0.8156 (3)	0.1798 (3)	0.5032 (3)	0.0390 (9)
H12A	0.8766	0.2393	0.4852	0.047*
H13A	0.7789	0.1969	0.5577	0.047*
C11A	0.8381 (4)	0.1090 (4)	0.5616 (4)	0.0599 (12)
H14A	0.8773	0.1387	0.6307	0.090*
H15A	0.8735	0.0909	0.5077	0.090*
H16A	0.7780	0.0516	0.5842	0.090*
C12A	0.6664 (3)	0.1737 (2)	0.2344 (3)	0.0296 (8)
O1B	0.4907 (4)	0.5561 (4)	0.3174 (4)	0.0335 (11)	0.50
O2B	0.5749 (4)	0.5444 (4)	0.4564 (5)	0.0459 (14)	0.50
O3B	0.5142 (6)	0.4340 (5)	0.3252 (7)	0.0320 (17)	0.50
N1B	0.5259 (4)	0.5112 (4)	0.3655 (5)	0.0297 (13)	0.50
O1C	0.4175 (5)	0.4683 (5)	0.3189 (4)	0.0493 (17)	0.50
O2C	0.3875 (4)	0.3783 (4)	0.4708 (4)	0.0406 (15)	0.50
O3C	0.4942 (6)	0.3893 (6)	0.3465 (7)	0.0385 (18)	0.50
N1C	0.4329 (4)	0.4118 (5)	0.3785 (6)	0.0373 (15)	0.50
C1D	0.0000	0.004 (2)	0.6667	0.086 (3)*	0.43 (4)
C2D	0.0188 (9)	−0.0011 (11)	0.7986 (15)	0.086 (3)*	0.496 (15)
C3D	−0.0050 (13)	−0.0225 (15)	0.613 (3)	0.086 (3)*	0.37 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0476 (16)	0.0418 (14)	0.0219 (13)	0.0255 (12)	0.0049 (11)	0.0024 (11)
O2A	0.0494 (16)	0.0280 (13)	0.0223 (14)	0.0084 (13)	0.0055 (12)	0.0014 (10)
O3A	0.0452 (15)	0.0320 (13)	0.0210 (13)	0.0161 (11)	0.0084 (11)	0.0053 (10)
N1A	0.0271 (15)	0.0440 (19)	0.0453 (19)	0.0116 (14)	0.0016 (14)	−0.0208 (15)
N2A	0.0411 (17)	0.0334 (14)	0.0159 (14)	0.0198 (13)	0.0073 (12)	0.0047 (12)
C1A	0.037 (2)	0.040 (2)	0.0217 (19)	0.0177 (17)	0.0016 (15)	−0.0101 (16)
C2A	0.037 (2)	0.040 (2)	0.022 (2)	0.0146 (17)	0.0048 (15)	−0.0050 (16)
C3A	0.047 (3)	0.044 (2)	0.059 (3)	0.010 (2)	0.013 (2)	−0.018 (2)
C4A	0.045 (2)	0.045 (2)	0.021 (2)	0.0226 (19)	0.0085 (16)	−0.0013 (16)
C5A	0.048 (2)	0.059 (3)	0.040 (2)	0.020 (2)	0.0124 (19)	−0.008 (2)
C6A	0.0344 (19)	0.0320 (18)	0.0172 (18)	0.0142 (15)	0.0000 (15)	−0.0063 (15)
C7A	0.0368 (19)	0.0334 (18)	0.0192 (18)	0.0170 (15)	0.0088 (15)	0.0013 (14)
C8A	0.045 (2)	0.040 (2)	0.0194 (18)	0.0240 (17)	0.0053 (16)	0.0007 (15)
C9A	0.049 (2)	0.057 (2)	0.031 (2)	0.034 (2)	0.0064 (18)	0.0002 (18)
C10A	0.050 (2)	0.042 (2)	0.026 (2)	0.0248 (19)	−0.0019 (17)	−0.0048 (16)
C11A	0.092 (4)	0.074 (3)	0.033 (3)	0.056 (3)	−0.011 (2)	−0.005 (2)
C12A	0.0406 (19)	0.0319 (18)	0.0202 (19)	0.0210 (17)	0.0090 (16)	0.0029 (14)
O1B	0.055 (3)	0.048 (3)	0.015 (3)	0.039 (3)	−0.005 (2)	0.002 (2)
O2B	0.046 (3)	0.055 (3)	0.035 (3)	0.023 (3)	−0.019 (2)	−0.008 (2)
O3B	0.053 (4)	0.039 (4)	0.024 (4)	0.038 (4)	0.000 (3)	−0.001 (3)
N1B	0.032 (3)	0.038 (3)	0.024 (3)	0.022 (3)	0.004 (3)	0.005 (3)
O1C	0.078 (4)	0.100 (5)	0.013 (3)	0.077 (5)	0.000 (3)	0.003 (3)
O2C	0.055 (3)	0.058 (3)	0.013 (5)	0.032 (3)	0.010 (3)	0.004 (2)
O3C	0.051 (5)	0.056 (5)	0.029 (4)	0.042 (5)	0.003 (3)	−0.002 (4)
N1C	0.041 (4)	0.055 (4)	0.031 (4)	0.036 (3)	−0.014 (3)	−0.011 (3)

Geometric parameters (Å, º)

O1A—C6A	1.246 (4)	C7A—C8A	1.526 (5)
O2A—C12A	1.291 (4)	C7A—C12A	1.536 (5)
O2A—H5A	0.79 (5)	C7A—H71A	1.0000
O3A—C12A	1.235 (4)	C8A—C9A	1.544 (5)
N1A—C1A	1.484 (5)	C8A—C10A	1.550 (5)
N1A—H1A	0.9100	C8A—H81A	1.0000
N1A—H2A	0.9100	C9A—H91A	0.9800
N1A—H3A	0.9100	C9A—H92A	0.9800
N2A—C6A	1.323 (4)	C9A—H93A	0.9800
N2A—C7A	1.462 (4)	C10A—C11A	1.513 (6)
N2A—H4A	0.8800	C10A—H12A	0.9900
C1A—C6A	1.519 (5)	C10A—H13A	0.9900
C1A—C2A	1.532 (5)	C11A—H14A	0.9800
C1A—H11A	1.0000	C11A—H15A	0.9800
C2A—C3A	1.516 (6)	C11A—H16A	0.9800
C2A—C4A	1.538 (5)	O1B—N1B	1.248 (7)
C2A—H21A	1.0000	O2B—N1B	1.259 (7)
C3A—H31A	0.9800	O2B—O2B^i	1.317 (11)
C3A—H32A	0.9800	O3B—N1B	1.247 (10)
C3A—H33A	0.9800	O1C—N1C	1.257 (8)
C4A—C5A	1.505 (6)	O2C—O2C^i	0.721 (8)
C4A—H41A	0.9900	O2C—N1C	1.250 (8)
C4A—H42A	0.9900	O3C—N1C	1.263 (10)
C5A—H51A	0.9800	C2D—C2D^ii	0.80 (3)
C5A—H52A	0.9800	C3D—C3D^iii	1.25 (8)
C5A—H53A	0.9800
C12A—O2A—H5A	116 (3)	N2A—C6A—C1A	118.4 (3)
C1A—N1A—H1A	109.5	N2A—C7A—C8A	110.7 (3)
C1A—N1A—H2A	109.5	N2A—C7A—C12A	109.6 (3)
H1A—N1A—H2A	109.5	C8A—C7A—C12A	111.5 (3)
C1A—N1A—H3A	109.5	N2A—C7A—H71A	108.3
H1A—N1A—H3A	109.5	C8A—C7A—H71A	108.3
H2A—N1A—H3A	109.5	C12A—C7A—H71A	108.3
C6A—N2A—C7A	120.3 (3)	C7A—C8A—C9A	110.3 (3)
C6A—N2A—H4A	119.9	C7A—C8A—C10A	109.9 (3)
C7A—N2A—H4A	119.9	C9A—C8A—C10A	110.8 (3)
N1A—C1A—C6A	104.6 (3)	C7A—C8A—H81A	108.6
N1A—C1A—C2A	110.4 (3)	C9A—C8A—H81A	108.6
C6A—C1A—C2A	113.6 (3)	C10A—C8A—H81A	108.6
N1A—C1A—H11A	109.4	C8A—C9A—H91A	109.5
C6A—C1A—H11A	109.4	C8A—C9A—H92A	109.5
C2A—C1A—H11A	109.4	H91A—C9A—H92A	109.5
C3A—C2A—C1A	110.1 (3)	C8A—C9A—H93A	109.5
C3A—C2A—C4A	111.7 (3)	H91A—C9A—H93A	109.5
C1A—C2A—C4A	110.4 (3)	H92A—C9A—H93A	109.5
C3A—C2A—H21A	108.2	C11A—C10A—C8A	113.0 (3)
C1A—C2A—H21A	108.2	C11A—C10A—H12A	109.0
C4A—C2A—H21A	108.2	C8A—C10A—H12A	109.0
C2A—C3A—H31A	109.5	C11A—C10A—H13A	109.0
C2A—C3A—H32A	109.5	C8A—C10A—H13A	109.0
H31A—C3A—H32A	109.5	H12A—C10A—H13A	107.8
C2A—C3A—H33A	109.5	C10A—C11A—H14A	109.5
H31A—C3A—H33A	109.5	C10A—C11A—H15A	109.5
H32A—C3A—H33A	109.5	H14A—C11A—H15A	109.5
C5A—C4A—C2A	114.7 (3)	C10A—C11A—H16A	109.5
C5A—C4A—H41A	108.6	H14A—C11A—H16A	109.5
C2A—C4A—H41A	108.6	H15A—C11A—H16A	109.5
C5A—C4A—H42A	108.6	O3A—C12A—O2A	125.2 (3)
C2A—C4A—H42A	108.6	O3A—C12A—C7A	121.2 (3)
H41A—C4A—H42A	107.6	O2A—C12A—C7A	113.5 (3)
C4A—C5A—H51A	109.5	N1B—O2B—O2B^i	121.6 (6)
C4A—C5A—H52A	109.5	O3B—N1B—O1B	121.5 (6)
H51A—C5A—H52A	109.5	O3B—N1B—O2B	118.9 (6)
C4A—C5A—H53A	109.5	O1B—N1B—O2B	119.5 (6)
H51A—C5A—H53A	109.5	O2C^i—O2C—N1C	147.4 (6)
H52A—C5A—H53A	109.5	O2C—N1C—O1C	119.6 (6)
O1A—C6A—N2A	121.8 (3)	O2C—N1C—O3C	119.7 (7)
O1A—C6A—C1A	119.8 (3)	O1C—N1C—O3C	120.7 (7)
N1A—C1A—C2A—C3A	165.2 (3)	C6A—N2A—C7A—C8A	178.6 (3)
C6A—C1A—C2A—C3A	48.1 (5)	C6A—N2A—C7A—C12A	−58.0 (4)
N1A—C1A—C2A—C4A	−71.0 (4)	N2A—C7A—C8A—C9A	171.8 (3)
C6A—C1A—C2A—C4A	171.9 (3)	C12A—C7A—C8A—C9A	49.5 (4)
C3A—C2A—C4A—C5A	−64.8 (5)	N2A—C7A—C8A—C10A	−65.7 (4)
C1A—C2A—C4A—C5A	172.3 (3)	C12A—C7A—C8A—C10A	171.9 (3)
C7A—N2A—C6A—O1A	6.6 (5)	C7A—C8A—C10A—C11A	163.9 (3)
C7A—N2A—C6A—C1A	−172.2 (3)	C9A—C8A—C10A—C11A	−74.0 (4)
N1A—C1A—C6A—O1A	−45.0 (4)	N2A—C7A—C12A—O3A	126.1 (3)
C2A—C1A—C6A—O1A	75.4 (4)	C8A—C7A—C12A—O3A	−111.0 (4)
N1A—C1A—C6A—N2A	133.8 (3)	N2A—C7A—C12A—O2A	−57.3 (4)
C2A—C1A—C6A—N2A	−105.8 (4)	C8A—C7A—C12A—O2A	65.6 (4)

Symmetry codes: (i) y, x, −z+1; (ii) x−y, −y, −z+5/3; (iii) −x, −x+y, −z+4/3.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H5A···O1B^iv	0.79 (5)	2.01 (5)	2.745 (5)	153 (5)
O2A—H5A···O1C^iv	0.79 (5)	1.80 (5)	2.543 (5)	156 (5)
N1A—H1A···O3A^v	0.91	2.17	3.051 (4)	161
N1A—H2A···O1B^i	0.91	2.29	2.914 (6)	126
N1A—H2A···O1C^i	0.91	2.05	2.824 (6)	142
N1A—H2A···O3A^vi	0.91	2.53	3.258 (4)	137
N1A—H3A···O2C	0.91	2.52	3.187 (8)	130
N1A—H3A···O3B	0.91	2.26	3.146 (8)	165
N1A—H3A···O3C	0.91	1.82	2.726 (9)	172
N2A—H4A···O3B^v	0.88	2.14	2.981 (8)	161
N2A—H4A···O3C^v	0.88	2.18	3.028 (4)	161
C1A—H11A···O1A^v	1.00	2.42	2.999 (4)	116
C1A—H11A···O3B^v	1.00	2.45	3.262 (9)	138

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

(IIdc) L-Isoleucyl-L-isoleucine L-Isoleucyl-L-isoleucinium nitrate acetonitrile solvate

Crystal data

C13.80H27.20N3.40O4.70	Dx = 1.147 Mg m^−3
Mr = 315.99	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P21212	Cell parameters from 3710 reflections
a = 16.2957 (19) Å	θ = 2.1–25.1°
b = 23.426 (2) Å	µ = 0.09 mm^−1
c = 9.5842 (9) Å	T = 105 K
V = 3658.7 (7) Å^3	Plate, colourless
Z = 8	0.55 × 0.42 × 0.05 mm
F(000) = 1371

Data collection

Siemens SMART CCD diffractometer	3657 independent reflections
Radiation source: fine-focus sealed tube	3276 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 8.3 pixels mm^-1	θmax = 25.1°, θmin = 2.1°
Sets of exposures each taken over 0.3° ω rotation scans	h = −15→19
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −27→27
Tmin = 0.804, Tmax = 0.996	l = −10→11
27666 measured reflections

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)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0659P)^2 + 1.4323P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max = 0.007
3657 reflections	Δρmax = 0.21 e Å^−3
449 parameters	Δρmin = −0.31 e Å^−3
48 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −4.9 (15)

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.71955 (13)	0.75538 (10)	0.2910 (2)	0.0329 (5)
O2A	0.52869 (12)	0.79839 (10)	−0.0783 (2)	0.0299 (5)
O3A	0.46408 (12)	0.80128 (9)	0.1229 (2)	0.0274 (5)
N1A	0.86800 (14)	0.73828 (11)	0.1502 (3)	0.0260 (5)
H1A	0.8705	0.7749	0.1262	0.039*
H2A	0.9102	0.7196	0.1127	0.039*
H3A	0.8701	0.7352	0.2427	0.039*
N2A	0.67233 (13)	0.77711 (10)	0.0752 (2)	0.0222 (5)
H4A	0.6760	0.7696	−0.0124	0.027*
C1A	0.78946 (16)	0.71314 (12)	0.0983 (3)	0.0228 (6)
H11A	0.7871	0.7160	−0.0037	0.027*
C2A	0.78003 (19)	0.65094 (13)	0.1428 (3)	0.0293 (7)
H21A	0.7825	0.6495	0.2449	0.035*
C3A	0.6961 (2)	0.62952 (17)	0.0978 (5)	0.0532 (10)
H31A	0.6542	0.6511	0.1445	0.080*
H32A	0.6907	0.5899	0.1216	0.080*
H33A	0.6903	0.6340	−0.0013	0.080*
C4A	0.8490 (2)	0.61318 (14)	0.0852 (4)	0.0372 (8)
H41A	0.8399	0.6072	−0.0138	0.045*
H42A	0.9008	0.6330	0.0959	0.045*
C5A	0.8547 (3)	0.55523 (15)	0.1573 (4)	0.0510 (10)
H51A	0.8979	0.5332	0.1155	0.077*
H52A	0.8036	0.5353	0.1472	0.077*
H53A	0.8663	0.5607	0.2546	0.077*
C6A	0.72271 (17)	0.75045 (13)	0.1633 (3)	0.0238 (6)
C7A	0.61117 (16)	0.81854 (12)	0.1215 (3)	0.0234 (6)
H71A	0.6044	0.8153	0.2228	0.028*
C8A	0.63771 (18)	0.87996 (13)	0.0854 (3)	0.0271 (6)
H81A	0.6486	0.8816	−0.0151	0.033*
C9A	0.5684 (2)	0.92237 (14)	0.1177 (4)	0.0370 (8)
H91A	0.5858	0.9603	0.0935	0.056*
H92A	0.5556	0.9209	0.2154	0.056*
H93A	0.5206	0.9125	0.0645	0.056*
C10A	0.7166 (2)	0.89629 (14)	0.1615 (4)	0.0360 (7)
H12A	0.7548	0.8646	0.1561	0.043*
H13A	0.7042	0.9027	0.2592	0.043*
C11A	0.7579 (2)	0.94970 (17)	0.1024 (5)	0.0546 (11)
H14A	0.8101	0.9552	0.1470	0.082*
H15A	0.7237	0.9823	0.1193	0.082*
H16A	0.7659	0.9452	0.0038	0.082*
C12A	0.52962 (17)	0.80423 (12)	0.0502 (3)	0.0235 (6)
O1B	0.21085 (12)	0.77175 (9)	0.21047 (19)	0.0278 (5)
O2B	0.40947 (12)	0.80032 (9)	0.5776 (2)	0.0283 (5)
O3B	0.47362 (12)	0.79735 (10)	0.3756 (2)	0.0278 (5)
H5B	0.467 (2)	0.7965 (15)	0.259 (4)	0.042*
N1B	0.06650 (14)	0.74491 (10)	0.3461 (2)	0.0224 (5)
H1B	0.0607	0.7818	0.3655	0.034*
H2B	0.0259	0.7253	0.3856	0.034*
H3B	0.0650	0.7399	0.2541	0.034*
N2B	0.26391 (13)	0.78810 (10)	0.4256 (2)	0.0212 (5)
H4B	0.2589	0.7813	0.5133	0.025*
C1B	0.14657 (16)	0.72440 (12)	0.4013 (3)	0.0218 (6)
H11B	0.1474	0.7283	0.5031	0.026*
C2B	0.16422 (17)	0.66244 (13)	0.3609 (3)	0.0263 (6)
H21B	0.1644	0.6600	0.2588	0.032*
C3B	0.2493 (2)	0.64503 (14)	0.4128 (4)	0.0385 (8)
H31B	0.2589	0.6056	0.3911	0.058*
H32B	0.2523	0.6504	0.5120	0.058*
H33B	0.2902	0.6681	0.3680	0.058*
C4B	0.0975 (2)	0.62174 (13)	0.4159 (4)	0.0342 (7)
H41B	0.1012	0.6200	0.5168	0.041*
H42B	0.0440	0.6372	0.3923	0.041*
C5B	0.1041 (3)	0.56190 (15)	0.3576 (5)	0.0505 (10)
H51B	0.0616	0.5385	0.3969	0.076*
H52B	0.1567	0.5461	0.3810	0.076*
H53B	0.0981	0.5631	0.2580	0.076*
C6B	0.21077 (17)	0.76373 (12)	0.3369 (3)	0.0209 (6)
C7B	0.32985 (16)	0.82576 (12)	0.3793 (3)	0.0219 (6)
H71B	0.3357	0.8225	0.2778	0.026*
C8B	0.31252 (18)	0.88884 (12)	0.4177 (3)	0.0264 (6)
H81B	0.3073	0.8909	0.5194	0.032*
C9B	0.3854 (2)	0.92630 (14)	0.3758 (4)	0.0359 (8)
H91B	0.3738	0.9653	0.3990	0.054*
H92B	0.3945	0.9231	0.2772	0.054*
H93B	0.4336	0.9140	0.4250	0.054*
C10B	0.2319 (2)	0.91053 (14)	0.3550 (4)	0.0379 (8)
H12B	0.2393	0.9163	0.2555	0.045*
H13B	0.1900	0.8816	0.3673	0.045*
C11B	0.2027 (3)	0.96571 (17)	0.4201 (5)	0.0649 (12)
H14B	0.1489	0.9747	0.3855	0.097*
H15B	0.2399	0.9959	0.3964	0.097*
H16B	0.2006	0.9615	0.5196	0.097*
C12B	0.40893 (17)	0.80596 (12)	0.4486 (3)	0.0213 (6)
O1C	0.4221 (5)	0.5919 (3)	0.5904 (10)	0.0579 (18)*	0.402 (9)
O2C	0.4382 (5)	0.6684 (3)	0.7244 (10)	0.0326 (13)*	0.402 (9)
O3C	0.5341 (9)	0.6419 (8)	0.586 (2)	0.046 (3)	0.402 (9)
N1C	0.4630 (5)	0.6351 (4)	0.6374 (11)	0.066 (3)	0.402 (9)
O4C	0.4125 (7)	0.5981 (4)	0.6358 (13)	0.0579 (18)*	0.324 (9)
O5C	0.4595 (5)	0.6669 (3)	0.7742 (10)	0.0326 (13)*	0.324 (9)
O6C	0.5202 (12)	0.6478 (10)	0.581 (2)	0.046 (3)	0.324 (9)
N2C	0.4631 (6)	0.6384 (5)	0.6687 (13)	0.066 (3)	0.324 (9)
O1D	0.5770 (10)	0.6682 (12)	0.442 (2)	0.031 (5)*	0.072 (3)
O2D	0.4415 (9)	0.6741 (12)	0.422 (2)	0.031 (5)*	0.072 (3)
O3D	0.5183 (14)	0.6776 (13)	0.2403 (15)	0.031 (5)*	0.072 (3)
N1D	0.5098 (10)	0.6729 (14)	0.3715 (16)	0.025*	0.072 (3)
O7C	0.4192 (10)	0.6775 (5)	0.671 (2)	0.056 (4)*	0.188 (9)
O8C	0.4423 (10)	0.5842 (5)	0.6772 (18)	0.056 (4)*	0.188 (9)
O9C	0.5259 (17)	0.6401 (11)	0.572 (5)	0.056 (4)*	0.188 (9)
N3C	0.4595 (9)	0.6320 (7)	0.638 (2)	0.026*	0.188 (9)
N1E	0.3627 (3)	0.67250 (18)	0.0672 (4)	0.0772 (15)	0.928 (3)
C1E	0.4074 (3)	0.6583 (2)	0.1440 (5)	0.0602 (13)	0.928 (3)
C2E	0.4675 (4)	0.6426 (3)	0.2515 (6)	0.096 (2)	0.928 (3)
H1E	0.5087	0.6184	0.2112	0.144*	0.928 (3)
H2E	0.4403	0.6227	0.3257	0.144*	0.928 (3)
H3E	0.4928	0.6765	0.2877	0.144*	0.928 (3)
N1F	0.3679 (5)	0.5112 (4)	0.2345 (9)	0.086 (3)*	0.483 (6)
C1F	0.4174 (5)	0.5097 (4)	0.3116 (9)	0.061 (3)*	0.483 (6)
C2F	0.4842 (6)	0.5057 (6)	0.4131 (9)	0.075 (3)*	0.483 (6)
H1F	0.5351	0.5153	0.3687	0.112*	0.483 (6)
H2F	0.4872	0.4674	0.4487	0.112*	0.483 (6)
H3F	0.4741	0.5317	0.4886	0.112*	0.483 (6)
N1G	0.5794 (8)	0.5053 (6)	0.0982 (12)	0.094 (4)*	0.401 (9)
C1G	0.5413 (9)	0.5034 (7)	0.0038 (14)	0.095 (5)*	0.401 (9)
C2G	0.5024 (18)	0.5133 (11)	−0.1324 (15)	0.117 (7)*	0.401 (9)
H1G	0.5428	0.5268	−0.1974	0.176*	0.401 (9)
H2G	0.4598	0.5413	−0.1227	0.176*	0.401 (9)
H3G	0.4792	0.4782	−0.1661	0.176*	0.401 (9)
O1W	0.505 (2)	0.5516 (15)	0.894 (3)	0.28 (2)*	0.39 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0309 (12)	0.0534 (14)	0.0145 (10)	0.0132 (11)	0.0004 (8)	0.0009 (9)
O2A	0.0215 (10)	0.0539 (13)	0.0143 (9)	0.0032 (10)	−0.0013 (8)	−0.0046 (10)
O3A	0.0179 (9)	0.0457 (12)	0.0186 (9)	0.0003 (9)	0.0011 (8)	−0.0010 (9)
N1A	0.0222 (12)	0.0359 (13)	0.0200 (12)	0.0041 (10)	−0.0016 (10)	0.0002 (11)
N2A	0.0161 (11)	0.0362 (13)	0.0144 (10)	0.0033 (10)	−0.0005 (9)	−0.0008 (10)
C1A	0.0190 (13)	0.0353 (16)	0.0142 (13)	0.0027 (12)	−0.0010 (11)	0.0016 (11)
C2A	0.0306 (16)	0.0358 (16)	0.0214 (14)	0.0003 (13)	0.0066 (13)	0.0014 (13)
C3A	0.038 (2)	0.047 (2)	0.074 (3)	−0.0097 (17)	0.004 (2)	0.000 (2)
C4A	0.0408 (19)	0.0346 (17)	0.0363 (18)	0.0058 (15)	0.0102 (16)	0.0034 (15)
C5A	0.068 (3)	0.0368 (18)	0.049 (2)	0.0099 (18)	0.012 (2)	0.0052 (17)
C6A	0.0200 (14)	0.0360 (15)	0.0156 (13)	0.0011 (12)	−0.0004 (11)	0.0043 (12)
C7A	0.0180 (13)	0.0350 (16)	0.0173 (13)	0.0035 (11)	−0.0015 (11)	−0.0006 (12)
C8A	0.0223 (14)	0.0373 (16)	0.0218 (14)	0.0018 (13)	−0.0004 (12)	0.0005 (13)
C9A	0.0338 (17)	0.0346 (17)	0.0427 (19)	0.0032 (14)	0.0018 (16)	0.0007 (15)
C10A	0.0302 (17)	0.0410 (18)	0.0369 (17)	−0.0057 (14)	−0.0046 (15)	−0.0021 (15)
C11A	0.038 (2)	0.054 (2)	0.072 (3)	−0.0158 (17)	−0.006 (2)	0.000 (2)
C12A	0.0191 (14)	0.0306 (15)	0.0208 (15)	0.0019 (12)	0.0012 (11)	0.0013 (12)
O1B	0.0249 (10)	0.0447 (12)	0.0139 (9)	−0.0084 (10)	−0.0011 (8)	0.0013 (8)
O2B	0.0192 (10)	0.0495 (13)	0.0162 (9)	−0.0001 (9)	−0.0009 (8)	0.0055 (9)
O3B	0.0189 (10)	0.0464 (12)	0.0181 (9)	0.0023 (9)	0.0031 (8)	0.0021 (9)
N1B	0.0185 (11)	0.0311 (12)	0.0175 (11)	−0.0038 (10)	0.0001 (9)	−0.0007 (10)
N2B	0.0175 (11)	0.0338 (13)	0.0122 (10)	−0.0038 (10)	0.0009 (9)	0.0032 (10)
C1B	0.0176 (13)	0.0336 (15)	0.0142 (13)	0.0003 (12)	−0.0009 (11)	−0.0004 (11)
C2B	0.0240 (15)	0.0350 (16)	0.0200 (14)	0.0013 (12)	0.0008 (12)	0.0002 (12)
C3B	0.0270 (16)	0.0388 (18)	0.050 (2)	0.0043 (14)	0.0019 (16)	0.0077 (17)
C4B	0.0329 (17)	0.0325 (16)	0.0371 (18)	−0.0036 (14)	0.0060 (15)	−0.0010 (15)
C5B	0.056 (2)	0.0339 (18)	0.061 (2)	−0.0048 (17)	0.011 (2)	−0.0038 (18)
C6B	0.0160 (13)	0.0300 (15)	0.0168 (13)	0.0009 (12)	0.0009 (11)	0.0004 (12)
C7B	0.0196 (13)	0.0312 (14)	0.0148 (13)	−0.0027 (11)	0.0018 (11)	0.0028 (11)
C8B	0.0240 (15)	0.0314 (15)	0.0238 (14)	0.0002 (12)	0.0000 (12)	0.0009 (13)
C9B	0.0359 (17)	0.0316 (17)	0.0403 (18)	−0.0058 (14)	−0.0018 (15)	0.0018 (15)
C10B	0.0340 (17)	0.0353 (17)	0.0444 (19)	0.0061 (14)	−0.0040 (16)	0.0076 (16)
C11B	0.060 (3)	0.058 (2)	0.077 (3)	0.028 (2)	−0.005 (3)	−0.002 (2)
C12B	0.0192 (14)	0.0262 (14)	0.0185 (14)	−0.0033 (12)	−0.0005 (11)	0.0015 (11)
O3C	0.023 (5)	0.037 (4)	0.077 (4)	0.001 (4)	0.005 (4)	−0.019 (3)
N1C	0.045 (3)	0.029 (3)	0.123 (8)	−0.015 (2)	0.012 (4)	−0.009 (4)
O6C	0.023 (5)	0.037 (4)	0.077 (4)	0.001 (4)	0.005 (4)	−0.019 (3)
N2C	0.045 (3)	0.029 (3)	0.123 (8)	−0.015 (2)	0.012 (4)	−0.009 (4)
N1E	0.122 (4)	0.061 (2)	0.049 (2)	−0.021 (3)	−0.034 (3)	0.024 (2)
C1E	0.075 (3)	0.055 (3)	0.051 (3)	−0.005 (2)	0.014 (3)	0.008 (2)
C2E	0.073 (4)	0.121 (5)	0.094 (5)	0.032 (4)	−0.011 (4)	0.015 (4)

Geometric parameters (Å, º)

O1A—C6A	1.230 (3)	C2B—C4B	1.539 (4)
O2A—C12A	1.239 (3)	C2B—H21B	0.9800
O3A—C12A	1.277 (3)	C3B—H31B	0.9600
O3A—H5B	1.31 (4)	C3B—H32B	0.9600
N1A—C1A	1.494 (4)	C3B—H33B	0.9600
N1A—H1A	0.8900	C4B—C5B	1.513 (5)
N1A—H2A	0.8900	C4B—H41B	0.9700
N1A—H3A	0.8900	C4B—H42B	0.9700
N2A—C6A	1.333 (4)	C5B—H51B	0.9600
N2A—C7A	1.460 (3)	C5B—H52B	0.9600
N2A—H4A	0.8600	C5B—H53B	0.9600
C1A—C2A	1.526 (4)	C7B—C12B	1.522 (4)
C1A—C6A	1.529 (4)	C7B—C8B	1.549 (4)
C1A—H11A	0.9800	C7B—H71B	0.9800
C2A—C3A	1.520 (5)	C8B—C9B	1.530 (4)
C2A—C4A	1.533 (4)	C8B—C10B	1.531 (4)
C2A—H21A	0.9800	C8B—H81B	0.9800
C3A—H31A	0.9600	C9B—H91B	0.9600
C3A—H32A	0.9600	C9B—H92B	0.9600
C3A—H33A	0.9600	C9B—H93B	0.9600
C4A—C5A	1.526 (5)	C10B—C11B	1.512 (5)
C4A—H41A	0.9700	C10B—H12B	0.9700
C4A—H42A	0.9700	C10B—H13B	0.9700
C5A—H51A	0.9600	C11B—H14B	0.9600
C5A—H52A	0.9600	C11B—H15B	0.9600
C5A—H53A	0.9600	C11B—H16B	0.9600
C7A—C12A	1.531 (4)	O1C—N1C	1.292 (10)
C7A—C8A	1.542 (4)	O2C—N1C	1.212 (9)
C7A—H71A	0.9800	O3C—N1C	1.270 (6)
C8A—C10A	1.527 (4)	O4C—N2C	1.292 (10)
C8A—C9A	1.535 (4)	O5C—N2C	1.212 (10)
C8A—H81A	0.9800	O6C—N2C	1.270 (6)
C9A—H91A	0.9600	O1D—N1D	1.291 (10)
C9A—H92A	0.9600	O2D—N1D	1.212 (10)
C9A—H93A	0.9600	O3D—N1D	1.270 (7)
C10A—C11A	1.529 (5)	O7C—N3C	1.292 (11)
C10A—H12A	0.9700	O8C—N3C	1.213 (10)
C10A—H13A	0.9700	O9C—N3C	1.270 (6)
C11A—H14A	0.9600	N1E—C1E	1.087 (6)
C11A—H15A	0.9600	C1E—C2E	1.468 (7)
C11A—H16A	0.9600	C2E—H1E	0.9600
O1B—C6B	1.226 (3)	C2E—H2E	0.9600
O2B—C12B	1.243 (3)	C2E—H3E	0.9600
O3B—C12B	1.281 (3)	N1F—C1F	1.095 (6)
O3B—H5B	1.13 (4)	C1F—C2F	1.463 (7)
N1B—C1B	1.488 (3)	C1F—C2F^i	1.910 (14)
N1B—H1B	0.8900	C2F—H1F	0.9600
N1B—H2B	0.8900	C2F—H2F	0.9600
N1B—H3B	0.8900	C2F—H3F	0.9600
N2B—C6B	1.341 (4)	N1G—C1G	1.098 (7)
N2B—C7B	1.459 (3)	C1G—C1G^i	1.35 (3)
N2B—H4B	0.8600	C1G—C2G	1.470 (8)
C1B—C6B	1.524 (4)	C1G—C2G^i	1.54 (3)
C1B—C2B	1.530 (4)	C2G—H1G	0.9600
C1B—H11B	0.9800	C2G—H2G	0.9600
C2B—C3B	1.529 (4)	C2G—H3G	0.9600
C12A—O3A—H5B	121.4 (15)	C6B—C1B—H11B	109.7
C1A—N1A—H1A	109.5	C2B—C1B—H11B	109.7
C1A—N1A—H2A	109.5	C3B—C2B—C1B	110.0 (3)
H1A—N1A—H2A	109.5	C3B—C2B—C4B	111.4 (3)
C1A—N1A—H3A	109.5	C1B—C2B—C4B	111.6 (2)
H1A—N1A—H3A	109.5	C3B—C2B—H21B	107.9
H2A—N1A—H3A	109.5	C1B—C2B—H21B	107.9
C6A—N2A—C7A	122.6 (2)	C4B—C2B—H21B	107.9
C6A—N2A—H4A	118.7	C2B—C3B—H31B	109.5
C7A—N2A—H4A	118.7	C2B—C3B—H32B	109.5
N1A—C1A—C2A	111.7 (2)	H31B—C3B—H32B	109.5
N1A—C1A—C6A	104.4 (2)	C2B—C3B—H33B	109.5
C2A—C1A—C6A	111.1 (2)	H31B—C3B—H33B	109.5
N1A—C1A—H11A	109.9	H32B—C3B—H33B	109.5
C2A—C1A—H11A	109.9	C5B—C4B—C2B	113.5 (3)
C6A—C1A—H11A	109.9	C5B—C4B—H41B	108.9
C3A—C2A—C1A	109.0 (3)	C2B—C4B—H41B	108.9
C3A—C2A—C4A	111.5 (3)	C5B—C4B—H42B	108.9
C1A—C2A—C4A	112.1 (2)	C2B—C4B—H42B	108.9
C3A—C2A—H21A	108.0	H41B—C4B—H42B	107.7
C1A—C2A—H21A	108.0	C4B—C5B—H51B	109.5
C4A—C2A—H21A	108.0	C4B—C5B—H52B	109.5
C2A—C3A—H31A	109.5	H51B—C5B—H52B	109.5
C2A—C3A—H32A	109.5	C4B—C5B—H53B	109.5
H31A—C3A—H32A	109.5	H51B—C5B—H53B	109.5
C2A—C3A—H33A	109.5	H52B—C5B—H53B	109.5
H31A—C3A—H33A	109.5	O1B—C6B—N2B	124.1 (3)
H32A—C3A—H33A	109.5	O1B—C6B—C1B	119.6 (2)
C5A—C4A—C2A	113.3 (3)	N2B—C6B—C1B	116.4 (2)
C5A—C4A—H41A	108.9	N2B—C7B—C12B	107.8 (2)
C2A—C4A—H41A	108.9	N2B—C7B—C8B	111.7 (2)
C5A—C4A—H42A	108.9	C12B—C7B—C8B	110.0 (2)
C2A—C4A—H42A	108.9	N2B—C7B—H71B	109.1
H41A—C4A—H42A	107.7	C12B—C7B—H71B	109.1
C4A—C5A—H51A	109.5	C8B—C7B—H71B	109.1
C4A—C5A—H52A	109.5	C9B—C8B—C10B	111.9 (3)
H51A—C5A—H52A	109.5	C9B—C8B—C7B	110.1 (2)
C4A—C5A—H53A	109.5	C10B—C8B—C7B	112.3 (3)
H51A—C5A—H53A	109.5	C9B—C8B—H81B	107.4
H52A—C5A—H53A	109.5	C10B—C8B—H81B	107.4
O1A—C6A—N2A	124.1 (3)	C7B—C8B—H81B	107.4
O1A—C6A—C1A	119.3 (3)	C8B—C9B—H91B	109.5
N2A—C6A—C1A	116.6 (2)	C8B—C9B—H92B	109.5
N2A—C7A—C12A	108.1 (2)	H91B—C9B—H92B	109.5
N2A—C7A—C8A	111.1 (2)	C8B—C9B—H93B	109.5
C12A—C7A—C8A	110.3 (2)	H91B—C9B—H93B	109.5
N2A—C7A—H71A	109.1	H92B—C9B—H93B	109.5
C12A—C7A—H71A	109.1	C11B—C10B—C8B	113.1 (3)
C8A—C7A—H71A	109.1	C11B—C10B—H12B	109.0
C10A—C8A—C9A	111.1 (3)	C8B—C10B—H12B	109.0
C10A—C8A—C7A	111.3 (2)	C11B—C10B—H13B	109.0
C9A—C8A—C7A	110.6 (2)	C8B—C10B—H13B	109.0
C10A—C8A—H81A	107.9	H12B—C10B—H13B	107.8
C9A—C8A—H81A	107.9	C10B—C11B—H14B	109.5
C7A—C8A—H81A	107.9	C10B—C11B—H15B	109.5
C8A—C9A—H91A	109.5	H14B—C11B—H15B	109.5
C8A—C9A—H92A	109.5	C10B—C11B—H16B	109.5
H91A—C9A—H92A	109.5	H14B—C11B—H16B	109.5
C8A—C9A—H93A	109.5	H15B—C11B—H16B	109.5
H91A—C9A—H93A	109.5	O2B—C12B—O3B	121.4 (3)
H92A—C9A—H93A	109.5	O2B—C12B—C7B	118.2 (3)
C8A—C10A—C11A	113.5 (3)	O3B—C12B—C7B	120.4 (2)
C8A—C10A—H12A	108.9	O2C—N1C—O3C	119.4 (7)
C11A—C10A—H12A	108.9	O2C—N1C—O1C	124.9 (5)
C8A—C10A—H13A	108.9	O3C—N1C—O1C	115.7 (8)
C11A—C10A—H13A	108.9	O5C—N2C—O6C	119.3 (7)
H12A—C10A—H13A	107.7	O5C—N2C—O4C	125.1 (6)
C10A—C11A—H14A	109.5	O6C—N2C—O4C	115.7 (8)
C10A—C11A—H15A	109.5	O2D—N1D—O3D	119.3 (8)
H14A—C11A—H15A	109.5	O2D—N1D—O1D	124.9 (6)
C10A—C11A—H16A	109.5	O3D—N1D—O1D	115.8 (9)
H14A—C11A—H16A	109.5	O8C—N3C—O9C	119.2 (8)
H15A—C11A—H16A	109.5	O8C—N3C—O7C	124.7 (6)
O2A—C12A—O3A	121.7 (3)	O9C—N3C—O7C	115.7 (10)
O2A—C12A—C7A	118.6 (3)	N1E—C1E—C2E	176.6 (6)
O3A—C12A—C7A	119.6 (2)	N1F—C1F—C2F	178.0 (12)
C12B—O3B—H5B	117.7 (18)	N1F—C1F—C2F^i	165.6 (10)
C1B—N1B—H1B	109.5	C2F—C1F—C2F^i	12.7 (6)
C1B—N1B—H2B	109.5	N1G—C1G—C1G^i	124.5 (10)
H1B—N1B—H2B	109.5	N1G—C1G—C2G	165.7 (17)
C1B—N1B—H3B	109.5	C1G^i—C1G—C2G	65.8 (12)
H1B—N1B—H3B	109.5	N1G—C1G—C2G^i	166 (2)
H2B—N1B—H3B	109.5	C1G^i—C1G—C2G^i	60.7 (10)
C6B—N2B—C7B	122.7 (2)	C2G—C1G—C2G^i	24.0 (19)
C6B—N2B—H4B	118.6	C1G—C2G—H1G	109.5
C7B—N2B—H4B	118.7	C1G—C2G—H2G	109.5
N1B—C1B—C6B	105.2 (2)	H1G—C2G—H2G	109.5
N1B—C1B—C2B	112.4 (2)	C1G—C2G—H3G	109.5
C6B—C1B—C2B	110.0 (2)	H1G—C2G—H3G	109.5
N1B—C1B—H11B	109.7	H2G—C2G—H3G	109.5
N1A—C1A—C2A—C3A	175.1 (3)	N1B—C1B—C2B—C3B	176.6 (2)
C6A—C1A—C2A—C3A	59.1 (3)	C6B—C1B—C2B—C3B	59.6 (3)
N1A—C1A—C2A—C4A	−60.9 (3)	N1B—C1B—C2B—C4B	−59.3 (3)
C6A—C1A—C2A—C4A	−177.0 (3)	C6B—C1B—C2B—C4B	−176.2 (2)
C3A—C2A—C4A—C5A	−72.7 (4)	C3B—C2B—C4B—C5B	−66.8 (4)
C1A—C2A—C4A—C5A	164.7 (3)	C1B—C2B—C4B—C5B	169.8 (3)
C7A—N2A—C6A—O1A	4.5 (5)	C7B—N2B—C6B—O1B	−2.1 (4)
C7A—N2A—C6A—C1A	−173.7 (2)	C7B—N2B—C6B—C1B	178.6 (2)
N1A—C1A—C6A—O1A	−57.5 (3)	N1B—C1B—C6B—O1B	−50.9 (3)
C2A—C1A—C6A—O1A	63.0 (4)	C2B—C1B—C6B—O1B	70.4 (3)
N1A—C1A—C6A—N2A	120.7 (3)	N1B—C1B—C6B—N2B	128.5 (2)
C2A—C1A—C6A—N2A	−118.8 (3)	C2B—C1B—C6B—N2B	−110.2 (3)
C6A—N2A—C7A—C12A	−133.1 (3)	C6B—N2B—C7B—C12B	−131.2 (3)
C6A—N2A—C7A—C8A	105.7 (3)	C6B—N2B—C7B—C8B	107.8 (3)
N2A—C7A—C8A—C10A	−63.1 (3)	N2B—C7B—C8B—C9B	176.4 (2)
C12A—C7A—C8A—C10A	177.0 (2)	C12B—C7B—C8B—C9B	56.7 (3)
N2A—C7A—C8A—C9A	172.9 (2)	N2B—C7B—C8B—C10B	−58.2 (3)
C12A—C7A—C8A—C9A	52.9 (3)	C12B—C7B—C8B—C10B	−178.0 (2)
C9A—C8A—C10A—C11A	−71.2 (4)	C9B—C8B—C10B—C11B	−70.6 (4)
C7A—C8A—C10A—C11A	165.0 (3)	C7B—C8B—C10B—C11B	165.0 (3)
N2A—C7A—C12A—O2A	−51.8 (4)	N2B—C7B—C12B—O2B	−52.9 (3)
C8A—C7A—C12A—O2A	69.9 (3)	C8B—C7B—C12B—O2B	69.2 (3)
N2A—C7A—C12A—O3A	131.5 (3)	N2B—C7B—C12B—O3B	129.4 (3)
C8A—C7A—C12A—O3A	−106.8 (3)	C8B—C7B—C12B—O3B	−108.5 (3)

Symmetry code: (i) −x+1, −y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3B—H5B···O3A	1.12 (3)	1.31 (3)	2.429 (3)	173 (3)
N1A—H1A···N1E^ii	0.89	2.23	2.952 (5)	138
N1A—H1A···O2C^iii	0.89	2.24	2.745 (7)	115
N1A—H2A···O2A^ii	0.89	2.00	2.841 (3)	156
N1A—H2A···O3A^ii	0.89	2.47	3.188 (3)	139
N1A—H3A···O2B^iii	0.89	2.02	2.843 (3)	154
N2A—H4A···O1B^ii	0.86	2.21	3.033 (3)	161
C1A—H11A···O1B^ii	0.98	2.36	3.244 (3)	150
N1B—H1B···O3C^iv	0.89	1.90	2.782 (15)	173
N1B—H1B···O1D^iv	0.89	2.20	2.88 (3)	133
N1B—H2B···O2B^iv	0.89	2.02	2.865 (3)	158
N1B—H2B···O3B^iv	0.89	2.50	3.223 (3)	139
N1B—H3B···O2A^v	0.89	2.00	2.828 (3)	155
N2B—H4B···O1A^iv	0.86	2.16	2.989 (3)	162
C1B—H11B···O1A^iv	0.98	2.33	3.215 (3)	150
C2F—H3F···O1C	0.96	1.91	2.827 (3)	158

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

(IIz) L-Isoleucyl-L-isoleucine dihydrate

Crystal data

C12H28N2O5	Dx = 1.187 Mg m^−3
Mr = 280.36	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 14734 reflections
a = 7.6341 (3) Å	θ = 2.1–35.0°
b = 12.5335 (6) Å	µ = 0.09 mm^−1
c = 16.3923 (7) Å	T = 105 K
V = 1568.45 (12) Å^3	Block, colourless
Z = 4	1.10 × 0.45 × 0.25 mm
F(000) = 616

Data collection

Siemens SMART CCD diffractometer	6861 independent reflections
Radiation source: fine-focus sealed tube	6294 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.3 pixels mm^-1	θmax = 35.0°, θmin = 2.1°
Sets of exposures each taken over 0.3° ω rotation scans	h = −12→12
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −19→20
Tmin = 0.848, Tmax = 0.978	l = −26→26
21646 measured reflections

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.0556P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
6861 reflections	Δρmax = 0.32 e Å^−3
210 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.2 (4)

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.

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

	x	y	z	Uiso*/Ueq
O1	−0.18949 (6)	0.31325 (5)	0.13844 (4)	0.02743 (11)
O2	−0.14950 (6)	0.59732 (4)	0.32756 (4)	0.02499 (11)
O3	−0.43548 (6)	0.56597 (4)	0.34837 (3)	0.02264 (10)
N1	0.15324 (7)	0.28687 (4)	0.09050 (3)	0.01639 (9)
H1	0.1437 (14)	0.2271 (9)	0.1236 (6)	0.025*
H2	0.2598 (15)	0.2909 (9)	0.0796 (6)	0.025*
H3	0.0938 (14)	0.2774 (9)	0.0435 (6)	0.025*
N2	−0.10005 (6)	0.42103 (4)	0.24256 (3)	0.01724 (9)
H4	−0.0199 (13)	0.4565 (9)	0.2636 (6)	0.021*
C1	0.09904 (7)	0.38781 (4)	0.13158 (3)	0.01466 (9)
H11	0.1826 (9)	0.40556 (19)	0.1719 (4)	0.018*
C2	0.09039 (8)	0.47867 (5)	0.06779 (4)	0.01819 (10)
H21	0.0151 (8)	0.4552 (3)	0.0244 (5)	0.022*
C3	0.01044 (10)	0.58070 (5)	0.10372 (5)	0.02514 (13)
H31	−0.1114 (10)	0.56710 (19)	0.1194 (4)	0.038*
H32	0.0140 (8)	0.6377 (5)	0.0628 (3)	0.038*
H33	0.0776 (7)	0.6025 (3)	0.1519 (4)	0.038*
C4	0.27317 (9)	0.49941 (6)	0.03070 (4)	0.02484 (13)
H41	0.3073 (3)	0.4374 (5)	−0.0010 (3)	0.030*
H42	0.26484 (12)	0.5594 (5)	−0.0065 (3)	0.030*
C5	0.41688 (10)	0.52274 (7)	0.09295 (5)	0.02961 (15)
H51	0.5233 (9)	0.5503 (7)	0.0641 (2)	0.044*
H52	0.4472 (8)	0.4556 (5)	0.1229 (4)	0.044*
H53	0.3744 (5)	0.5776 (6)	0.1327 (4)	0.044*
C6	−0.07799 (7)	0.36975 (5)	0.17218 (4)	0.01611 (10)
C7	−0.26939 (7)	0.42941 (5)	0.28367 (4)	0.01535 (9)
H71	−0.3582 (9)	0.42214 (9)	0.2444 (4)	0.018*
C8	−0.29109 (8)	0.33920 (5)	0.34763 (4)	0.01819 (10)
H81	−0.2492 (5)	0.2747 (8)	0.3231 (3)	0.022*
C9	−0.17735 (11)	0.36074 (7)	0.42257 (5)	0.02926 (15)
H91	−0.1844 (9)	0.3008 (6)	0.4594 (4)	0.044*
H92	−0.2185 (8)	0.4242 (6)	0.4498 (4)	0.044*
H93	−0.0573 (10)	0.3708 (7)	0.40578 (16)	0.044*
C10	−0.48263 (9)	0.31989 (6)	0.37261 (4)	0.02383 (12)
H101	−0.48484 (10)	0.2680 (4)	0.4173 (4)	0.029*
H102	−0.5315 (4)	0.3868 (6)	0.39343 (19)	0.029*
C11	−0.59937 (10)	0.27942 (7)	0.30414 (5)	0.03235 (15)
H111	−0.7120 (10)	0.2635 (7)	0.3252 (2)	0.049*
H112	−0.5497 (7)	0.2169 (6)	0.2813 (4)	0.049*
H113	−0.6092 (9)	0.3326 (5)	0.2633 (4)	0.049*
C12	−0.28492 (8)	0.54105 (5)	0.32253 (4)	0.01738 (10)
O1W	0.78097 (7)	0.04139 (6)	0.20519 (4)	0.03645 (15)
H11W	0.686 (2)	0.0479 (13)	0.1831 (9)	0.055*
H12W	0.841 (2)	0.0854 (13)	0.1836 (10)	0.055*
O2W	0.50836 (6)	0.24232 (4)	0.06819 (3)	0.01836 (8)
H21W	0.5848 (16)	0.2646 (10)	0.0939 (7)	0.028*
H22W	0.4767 (15)	0.1866 (10)	0.0962 (7)	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.01726 (19)	0.0338 (3)	0.0312 (3)	−0.00742 (19)	0.00188 (18)	−0.0152 (2)
O2	0.0208 (2)	0.0186 (2)	0.0355 (3)	−0.00283 (16)	0.00355 (18)	−0.00871 (19)
O3	0.01754 (18)	0.01755 (19)	0.0328 (2)	0.00288 (15)	0.00169 (17)	−0.00418 (18)
N1	0.01476 (19)	0.0150 (2)	0.0194 (2)	0.00098 (16)	0.00065 (16)	0.00038 (17)
N2	0.01460 (18)	0.0186 (2)	0.0185 (2)	−0.00224 (16)	0.00014 (16)	−0.00404 (17)
C1	0.01430 (19)	0.0139 (2)	0.0158 (2)	−0.00096 (17)	−0.00064 (17)	−0.00055 (17)
C2	0.0215 (2)	0.0153 (2)	0.0178 (2)	−0.0004 (2)	−0.0027 (2)	0.00175 (19)
C3	0.0336 (3)	0.0147 (3)	0.0271 (3)	0.0022 (2)	−0.0025 (3)	0.0015 (2)
C4	0.0269 (3)	0.0261 (3)	0.0215 (3)	−0.0033 (2)	0.0026 (2)	0.0067 (2)
C5	0.0235 (3)	0.0321 (4)	0.0332 (3)	−0.0088 (3)	0.0005 (3)	0.0065 (3)
C6	0.01441 (19)	0.0152 (2)	0.0187 (2)	−0.00094 (18)	−0.00023 (18)	−0.00143 (19)
C7	0.01466 (19)	0.0148 (2)	0.0166 (2)	0.00010 (18)	−0.00051 (17)	−0.00140 (18)
C8	0.0221 (2)	0.0152 (2)	0.0173 (2)	0.00249 (19)	−0.0004 (2)	−0.00053 (19)
C9	0.0369 (3)	0.0296 (3)	0.0213 (3)	0.0060 (3)	−0.0098 (3)	0.0001 (3)
C10	0.0282 (3)	0.0191 (3)	0.0242 (3)	−0.0018 (2)	0.0083 (2)	0.0001 (2)
C11	0.0265 (3)	0.0320 (4)	0.0385 (4)	−0.0078 (3)	−0.0011 (3)	0.0047 (3)
C12	0.0182 (2)	0.0146 (2)	0.0194 (2)	0.00158 (18)	−0.00108 (18)	−0.00134 (19)
O1W	0.0197 (2)	0.0466 (4)	0.0430 (3)	−0.0021 (2)	−0.0063 (2)	0.0209 (3)
O2W	0.01626 (17)	0.0180 (2)	0.0208 (2)	−0.00309 (15)	−0.00210 (15)	−0.00033 (16)

Geometric parameters (Å, º)

O1—C6	1.2377 (7)	C5—H51	1.0012
O2—C12	1.2542 (8)	C5—H52	1.0012
O3—C12	1.2641 (7)	C5—H53	1.0012
N1—C1	1.4918 (8)	C7—C12	1.5420 (8)
N1—H1	0.928 (11)	C7—C8	1.5509 (8)
N1—H2	0.835 (11)	C7—H71	0.9398
N1—H3	0.903 (10)	C8—C9	1.5283 (10)
N2—C6	1.3314 (8)	C8—C10	1.5377 (9)
N2—C7	1.4616 (7)	C8—H81	0.9583
N2—H4	0.831 (11)	C9—H91	0.9650
C1—C6	1.5233 (8)	C9—H92	0.9650
C1—C2	1.5474 (8)	C9—H93	0.9650
C1—H11	0.9448	C10—C11	1.5202 (11)
C2—C3	1.5345 (9)	C10—H101	0.9796
C2—C4	1.5441 (9)	C10—H102	0.9796
C2—H21	0.9606	C11—H111	0.9476
C3—H31	0.9799	C11—H112	0.9476
C3—H32	0.9799	C11—H113	0.9476
C3—H33	0.9799	O1W—H11W	0.811 (16)
C4—C5	1.5266 (11)	O1W—H12W	0.801 (17)
C4—H41	0.9703	O2W—H21W	0.772 (12)
C4—H42	0.9703	O2W—H22W	0.870 (12)
C1—N1—H1	113.5 (7)	O1—C6—N2	125.20 (6)
C1—N1—H2	108.5 (8)	O1—C6—C1	120.00 (5)
H1—N1—H2	104.5 (10)	N2—C6—C1	114.78 (5)
C1—N1—H3	110.9 (7)	N2—C7—C12	108.89 (5)
H1—N1—H3	110.8 (10)	N2—C7—C8	110.72 (5)
H2—N1—H3	108.3 (10)	C12—C7—C8	111.97 (5)
C6—N2—C7	123.10 (5)	N2—C7—H71	108.4
C6—N2—H4	121.6 (7)	C12—C7—H71	108.4
C7—N2—H4	115.0 (7)	C8—C7—H71	108.4
N1—C1—C6	108.50 (4)	C9—C8—C10	110.74 (6)
N1—C1—C2	109.32 (5)	C9—C8—C7	110.73 (5)
C6—C1—C2	111.51 (5)	C10—C8—C7	113.35 (5)
N1—C1—H11	109.2	C9—C8—H81	107.2
C6—C1—H11	109.2	C10—C8—H81	107.2
C2—C1—H11	109.2	C7—C8—H81	107.2
C3—C2—C4	111.73 (6)	C8—C9—H91	109.5
C3—C2—C1	111.77 (5)	C8—C9—H92	109.5
C4—C2—C1	110.58 (5)	H91—C9—H92	109.5
C3—C2—H21	107.5	C8—C9—H93	109.5
C4—C2—H21	107.5	H91—C9—H93	109.5
C1—C2—H21	107.5	H92—C9—H93	109.5
C2—C3—H31	109.5	C11—C10—C8	114.42 (6)
C2—C3—H32	109.5	C11—C10—H101	108.7
H31—C3—H32	109.5	C8—C10—H101	108.7
C2—C3—H33	109.5	C11—C10—H102	108.7
H31—C3—H33	109.5	C8—C10—H102	108.7
H32—C3—H33	109.5	H101—C10—H102	107.6
C5—C4—C2	114.73 (6)	C10—C11—H111	109.5
C5—C4—H41	108.6	C10—C11—H112	109.5
C2—C4—H41	108.6	H111—C11—H112	109.5
C5—C4—H42	108.6	C10—C11—H113	109.5
C2—C4—H42	108.6	H111—C11—H113	109.5
H41—C4—H42	107.6	H112—C11—H113	109.5
C4—C5—H51	109.5	O2—C12—O3	126.05 (6)
C4—C5—H52	109.5	O2—C12—C7	118.30 (5)
H51—C5—H52	109.5	O3—C12—C7	115.63 (5)
C4—C5—H53	109.5	H11W—O1W—H12W	104.3 (15)
H51—C5—H53	109.5	H21W—O2W—H22W	102.2 (11)
H52—C5—H53	109.5
N1—C1—C2—C3	171.90 (5)	C6—N2—C7—C12	−142.51 (6)
C6—C1—C2—C3	51.93 (6)	C6—N2—C7—C8	93.98 (7)
N1—C1—C2—C4	−62.94 (6)	N2—C7—C8—C9	73.77 (6)
C6—C1—C2—C4	177.09 (5)	C12—C7—C8—C9	−47.94 (7)
C3—C2—C4—C5	70.24 (8)	N2—C7—C8—C10	−161.08 (5)
C1—C2—C4—C5	−54.94 (8)	C12—C7—C8—C10	77.21 (6)
C7—N2—C6—O1	−9.11 (10)	C9—C8—C10—C11	−170.15 (6)
C7—N2—C6—C1	168.96 (5)	C7—C8—C10—C11	64.71 (7)
N1—C1—C6—O1	−37.12 (8)	N2—C7—C12—O2	−12.99 (8)
C2—C1—C6—O1	83.33 (7)	C8—C7—C12—O2	109.77 (6)
N1—C1—C6—N2	144.70 (5)	N2—C7—C12—O3	168.66 (5)
C2—C1—C6—N2	−94.85 (6)	C8—C7—C12—O3	−68.58 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.928 (11)	1.814 (11)	2.7293 (7)	168.7 (10)
N1—H2···O2w	0.835 (11)	2.001 (12)	2.7920 (7)	157.8 (11)
N1—H3···O2W^ii	0.903 (10)	1.959 (10)	2.8502 (7)	169.2 (10)
N2—H4···O1W^iii	0.831 (11)	2.173 (11)	2.9905 (8)	167.9 (9)
O1W—H11W···O3^i	0.811 (16)	1.997 (16)	2.7968 (7)	168.5 (15)
O1W—H12W···O2^iv	0.801 (17)	2.364 (15)	2.9487 (8)	130.6 (14)
O2W—H21W···O1^v	0.772 (12)	1.969 (13)	2.7271 (7)	167.5 (12)
O2W—H22W···O3^i	0.870 (12)	1.792 (13)	2.6582 (7)	173.6 (11)

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

(IIa) Ammonium L-Leucyl-L-Leucinate

Crystal data

C12H27N3O3	Z = 2
Mr = 261.37	F(000) = 288
Triclinic, P1	Dx = 1.137 Mg m^−3
a = 6.7765 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.718 (2) Å	Cell parameters from 2001 reflections
c = 11.882 (3) Å	θ = 2.1–26.4°
α = 81.580 (3)°	µ = 0.08 mm^−1
β = 80.484 (3)°	T = 105 K
γ = 88.350 (3)°	Block, colourless
V = 763.4 (3) Å^3	0.55 × 0.24 × 0.22 mm

Data collection

Siemens SMART CCD diffractometer	3063 independent reflections
Radiation source: fine-focus sealed tube	2165 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 8.3 pixels mm^-1	θmax = 26.4°, θmin = 2.1°
Sets of exposures each taken over 0.3° ω rotation scans	h = −8→8
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −11→12
Tmin = 0.779, Tmax = 0.982	l = −14→14
6449 measured reflections

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0564P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.005
3063 reflections	Δρmax = 0.32 e Å^−3
395 parameters	Δρmin = −0.23 e Å^−3
11 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.7 (14)

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.

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

	x	y	z	Uiso*/Ueq
O1A	0.5836 (4)	0.3982 (3)	0.6181 (2)	0.0269 (6)
O2A	0.7905 (4)	0.8472 (3)	0.6621 (2)	0.0277 (6)
O3A	0.5084 (4)	0.9027 (3)	0.5900 (2)	0.0288 (7)
N1A	1.0889 (5)	0.4805 (4)	0.6284 (3)	0.0269 (8)
H1A	1.103 (7)	0.531 (5)	0.555 (4)	0.040*
H2A	1.206 (7)	0.443 (5)	0.639 (4)	0.040*
N2A	0.7137 (5)	0.5758 (3)	0.6874 (3)	0.0233 (7)
H4A	0.824 (7)	0.613 (4)	0.691 (3)	0.028*
C1A	0.9288 (5)	0.3754 (4)	0.6519 (3)	0.0228 (9)
H11A	0.9511 (10)	0.310 (3)	0.585 (3)	0.027*
C2A	0.9368 (6)	0.2845 (4)	0.7702 (4)	0.0311 (10)
H21A	0.9466 (8)	0.344 (3)	0.824 (3)	0.037*
C3A	0.7488 (7)	0.1952 (5)	0.8139 (4)	0.0394 (11)
H31A	0.627 (4)	0.2567 (18)	0.817 (2)	0.059*
H32A	0.756 (2)	0.145 (3)	0.893 (2)	0.059*
H33A	0.740 (2)	0.126 (3)	0.760 (2)	0.059*
C4A	1.1300 (7)	0.1904 (6)	0.7605 (5)	0.0564 (15)
H41A	1.1137 (8)	0.117 (3)	0.708 (2)	0.068*
H42A	1.251 (5)	0.252 (2)	0.7209 (16)	0.068*
C5A	1.1752 (9)	0.1163 (6)	0.8742 (5)	0.0603 (15)
H51A	1.322 (5)	0.048 (3)	0.8579 (7)	0.090*
H52A	1.040 (4)	0.043 (3)	0.920 (2)	0.090*
H53A	1.200 (5)	0.199 (2)	0.934 (2)	0.090*
C6A	0.7265 (5)	0.4512 (4)	0.6511 (3)	0.0228 (9)
C7A	0.5416 (6)	0.6692 (4)	0.6856 (3)	0.0229 (9)
H71A	0.467 (3)	0.6445 (12)	0.632 (2)	0.027*
C8A	0.4034 (5)	0.6575 (4)	0.8042 (3)	0.0230 (9)
H81A	0.3587 (17)	0.552 (4)	0.8273 (9)	0.028*
C9A	0.5161 (6)	0.6937 (5)	0.8987 (4)	0.0339 (10)
H91A	0.426 (3)	0.678 (3)	0.975 (2)	0.051*
H92A	0.557 (4)	0.794 (3)	0.8809 (13)	0.051*
H93A	0.638 (4)	0.633 (2)	0.9013 (16)	0.051*
C10A	0.2133 (6)	0.7451 (4)	0.7979 (4)	0.0269 (9)
H12A	0.2515 (12)	0.846 (3)	0.7797 (7)	0.032*
H13A	0.150 (2)	0.7214 (8)	0.733 (2)	0.032*
C11A	0.0593 (7)	0.7251 (5)	0.9080 (4)	0.0405 (12)
H14A	−0.060 (4)	0.782 (3)	0.8962 (10)	0.061*
H15A	0.117 (2)	0.754 (3)	0.971 (2)	0.061*
H16A	0.022 (4)	0.627 (3)	0.9273 (16)	0.061*
C12A	0.6197 (5)	0.8182 (4)	0.6423 (3)	0.0219 (9)
O1B	0.1411 (4)	0.6810 (3)	0.3736 (2)	0.0256 (6)
O2B	0.3897 (4)	0.2238 (3)	0.3336 (2)	0.0257 (6)
O3B	0.0690 (4)	0.1764 (3)	0.4097 (2)	0.0254 (6)
N1B	0.6565 (5)	0.5926 (3)	0.3610 (3)	0.0256 (8)
H1B	0.620 (7)	0.560 (5)	0.439 (4)	0.038*
H2B	0.759 (7)	0.642 (5)	0.356 (4)	0.038*
N2B	0.3177 (5)	0.4984 (3)	0.3075 (3)	0.0246 (8)
H4B	0.422 (7)	0.476 (5)	0.296 (4)	0.029*
C1B	0.5046 (5)	0.6980 (4)	0.3318 (3)	0.0216 (9)
H11B	0.4888 (8)	0.768 (3)	0.390 (2)	0.026*
C2B	0.5699 (6)	0.7771 (4)	0.2089 (3)	0.0247 (9)
H21B	0.5806 (7)	0.708 (3)	0.155 (2)	0.030*
C3B	0.4130 (6)	0.8857 (4)	0.1750 (4)	0.0341 (10)
H31B	0.461 (2)	0.936 (2)	0.094 (2)	0.051*
H32B	0.393 (3)	0.956 (2)	0.231 (2)	0.051*
H33B	0.282 (4)	0.8376 (13)	0.177 (2)	0.051*
C4B	0.7794 (6)	0.8438 (4)	0.1959 (4)	0.0309 (10)
H41B	0.880 (3)	0.768 (2)	0.2040 (4)	0.037*
H42B	0.8127 (12)	0.8962 (15)	0.117 (2)	0.037*
C5B	0.7962 (6)	0.9417 (4)	0.2828 (4)	0.0376 (11)
H51B	0.935 (4)	0.982 (3)	0.2677 (16)	0.056*
H52B	0.769 (4)	0.8887 (15)	0.363 (2)	0.056*
H53B	0.695 (4)	1.019 (3)	0.2751 (17)	0.056*
C6B	0.3049 (6)	0.6243 (4)	0.3399 (3)	0.0216 (9)
C7B	0.1450 (5)	0.4066 (4)	0.3120 (3)	0.0210 (8)
H71B	0.031 (4)	0.4360 (12)	0.369 (2)	0.025*
C8B	0.0755 (5)	0.4191 (4)	0.1928 (3)	0.0229 (9)
H81B	0.0384 (17)	0.517 (4)	0.1718 (10)	0.027*
C9B	0.2417 (6)	0.3835 (5)	0.0985 (4)	0.0327 (10)
H91B	0.1978 (19)	0.404 (3)	0.025 (2)	0.049*
H92B	0.274 (3)	0.286 (3)	0.1127 (14)	0.049*
H93B	0.359 (3)	0.437 (3)	0.0984 (16)	0.049*
C10B	−0.1134 (6)	0.3316 (4)	0.2020 (3)	0.0253 (9)
H12B	−0.0752 (11)	0.228 (3)	0.2155 (6)	0.030*
H13B	−0.214 (3)	0.3521 (7)	0.273 (2)	0.030*
C11B	−0.2151 (6)	0.3585 (5)	0.0962 (4)	0.0393 (11)
H14B	−0.336 (4)	0.301 (3)	0.1088 (11)	0.059*
H15B	−0.123 (3)	0.335 (3)	0.029 (2)	0.059*
H16B	−0.252 (4)	0.457 (3)	0.0825 (15)	0.059*
C12B	0.2064 (5)	0.2561 (4)	0.3558 (3)	0.0215 (8)
N1C	0.6475 (5)	0.1665 (3)	0.4928 (3)	0.0235 (7)
H1C	0.626 (6)	0.231 (3)	0.536 (3)	0.035*
H2C	0.572 (6)	0.186 (4)	0.438 (3)	0.035*
H3C	0.614 (6)	0.086 (3)	0.533 (3)	0.035*
H4C	0.768 (4)	0.185 (5)	0.463 (4)	0.035*
N1D	0.1408 (5)	0.9069 (3)	0.5061 (3)	0.0235 (7)
H1D	0.134 (6)	0.845 (4)	0.462 (3)	0.035*
H2D	0.044 (5)	0.892 (4)	0.565 (3)	0.035*
H3D	0.142 (6)	0.994 (2)	0.470 (3)	0.035*
H4D	0.244 (4)	0.909 (4)	0.539 (3)	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0209 (15)	0.0231 (15)	0.0387 (17)	−0.0027 (12)	−0.0076 (12)	−0.0070 (12)
O2A	0.0176 (14)	0.0267 (15)	0.0385 (16)	−0.0042 (12)	−0.0036 (12)	−0.0041 (12)
O3A	0.0219 (15)	0.0230 (15)	0.0410 (17)	−0.0026 (12)	−0.0110 (12)	0.0042 (12)
N1A	0.0206 (19)	0.026 (2)	0.035 (2)	−0.0026 (15)	−0.0066 (16)	−0.0040 (16)
N2A	0.0142 (16)	0.0195 (18)	0.038 (2)	−0.0001 (13)	−0.0065 (14)	−0.0075 (14)
C1A	0.017 (2)	0.022 (2)	0.030 (2)	−0.0003 (16)	−0.0048 (16)	−0.0048 (17)
C2A	0.031 (2)	0.031 (2)	0.033 (2)	0.0003 (18)	−0.0120 (18)	−0.0033 (19)
C3A	0.035 (3)	0.036 (3)	0.042 (3)	−0.006 (2)	−0.007 (2)	0.011 (2)
C4A	0.034 (3)	0.056 (3)	0.074 (4)	−0.003 (3)	−0.023 (3)	0.025 (3)
C5A	0.064 (4)	0.053 (3)	0.071 (4)	0.003 (3)	−0.033 (3)	−0.007 (3)
C6A	0.021 (2)	0.019 (2)	0.028 (2)	−0.0052 (16)	−0.0022 (16)	−0.0015 (16)
C7A	0.021 (2)	0.019 (2)	0.030 (2)	0.0027 (16)	−0.0099 (17)	−0.0060 (16)
C8A	0.018 (2)	0.023 (2)	0.028 (2)	−0.0052 (16)	−0.0048 (16)	−0.0022 (16)
C9A	0.025 (2)	0.048 (3)	0.029 (2)	−0.002 (2)	−0.0077 (18)	−0.004 (2)
C10A	0.022 (2)	0.027 (2)	0.033 (2)	0.0008 (17)	−0.0052 (17)	−0.0050 (17)
C11A	0.027 (2)	0.049 (3)	0.043 (3)	0.003 (2)	−0.002 (2)	−0.001 (2)
C12A	0.018 (2)	0.025 (2)	0.024 (2)	−0.0012 (17)	−0.0019 (16)	−0.0072 (17)
O1B	0.0155 (14)	0.0199 (15)	0.0422 (17)	−0.0007 (11)	−0.0041 (12)	−0.0072 (12)
O2B	0.0184 (15)	0.0249 (15)	0.0342 (15)	0.0006 (11)	−0.0047 (12)	−0.0053 (12)
O3B	0.0169 (14)	0.0190 (14)	0.0391 (16)	−0.0024 (11)	−0.0051 (11)	0.0013 (12)
N1B	0.0180 (18)	0.0204 (19)	0.038 (2)	−0.0046 (14)	−0.0051 (15)	−0.0018 (16)
N2B	0.0172 (17)	0.0176 (18)	0.040 (2)	−0.0018 (14)	−0.0060 (15)	−0.0071 (14)
C1B	0.018 (2)	0.019 (2)	0.028 (2)	−0.0005 (16)	−0.0057 (16)	−0.0054 (16)
C2B	0.025 (2)	0.023 (2)	0.027 (2)	−0.0033 (16)	−0.0021 (16)	−0.0065 (17)
C3B	0.028 (2)	0.029 (2)	0.044 (3)	−0.0020 (19)	−0.0127 (19)	0.0043 (19)
C4B	0.022 (2)	0.027 (2)	0.042 (3)	−0.0061 (17)	−0.0005 (18)	−0.0029 (19)
C5B	0.026 (2)	0.029 (2)	0.060 (3)	−0.0074 (19)	−0.005 (2)	−0.013 (2)
C6B	0.020 (2)	0.018 (2)	0.026 (2)	−0.0052 (16)	−0.0053 (16)	0.0002 (16)
C7B	0.0159 (19)	0.0161 (19)	0.031 (2)	−0.0009 (15)	−0.0030 (16)	−0.0042 (16)
C8B	0.022 (2)	0.016 (2)	0.031 (2)	−0.0004 (16)	−0.0062 (17)	−0.0005 (16)
C9B	0.023 (2)	0.041 (3)	0.033 (2)	−0.0036 (19)	−0.0052 (18)	0.0010 (19)
C10B	0.022 (2)	0.023 (2)	0.033 (2)	−0.0011 (17)	−0.0090 (17)	−0.0047 (17)
C11B	0.020 (2)	0.063 (3)	0.037 (3)	−0.007 (2)	−0.0124 (19)	−0.002 (2)
C12B	0.019 (2)	0.023 (2)	0.025 (2)	−0.0037 (17)	−0.0087 (16)	−0.0064 (17)
N1C	0.0182 (18)	0.0195 (19)	0.034 (2)	−0.0056 (15)	−0.0060 (15)	−0.0038 (15)
N1D	0.0197 (18)	0.0185 (18)	0.034 (2)	−0.0026 (15)	−0.0065 (15)	−0.0071 (15)

Geometric parameters (Å, º)

O1A—C6A	1.253 (4)	N1B—H1B	0.93 (5)
O2A—C12A	1.266 (4)	N1B—H2B	0.85 (5)
O3A—C12A	1.265 (5)	N2B—C6B	1.332 (5)
N1A—C1A	1.476 (5)	N2B—C7B	1.481 (5)
N1A—H1A	0.93 (5)	N2B—H4B	0.73 (4)
N1A—H2A	0.88 (5)	C1B—C6B	1.532 (5)
N2A—C6A	1.340 (5)	C1B—C2B	1.549 (5)
N2A—C7A	1.458 (5)	C1B—H11B	1.0291
N2A—H4A	0.85 (4)	C2B—C3B	1.536 (6)
C1A—C6A	1.538 (5)	C2B—C4B	1.553 (5)
C1A—C2A	1.555 (6)	C2B—H21B	0.9904
C1A—H11A	1.0816	C3B—H31B	1.0139
C2A—C3A	1.536 (6)	C3B—H32B	1.0139
C2A—C4A	1.573 (7)	C3B—H33B	1.0139
C2A—H21A	0.9309	C4B—C5B	1.522 (6)
C3A—H31A	1.0048	C4B—H41B	0.9935
C3A—H32A	1.0048	C4B—H42B	0.9935
C3A—H33A	1.0048	C5B—H51B	1.0076
C4A—C5A	1.510 (7)	C5B—H52B	1.0076
C4A—H41A	1.0329	C5B—H53B	1.0076
C4A—H42A	1.0329	C7B—C12B	1.548 (5)
C5A—H51A	1.1830	C7B—C8B	1.552 (5)
C5A—H52A	1.1830	C7B—H71B	1.0061
C5A—H53A	1.1830	C8B—C9B	1.522 (6)
C7A—C12A	1.542 (5)	C8B—C10B	1.537 (5)
C7A—C8A	1.549 (5)	C8B—H81B	0.9810
C7A—H71A	0.9309	C9B—H91B	0.9638
C8A—C10A	1.529 (6)	C9B—H92B	0.9638
C8A—C9A	1.544 (5)	C9B—H93B	0.9638
C8A—H81A	1.0584	C10B—C11B	1.517 (6)
C9A—H91A	1.0007	C10B—H12B	1.0300
C9A—H92A	1.0007	C10B—H13B	1.0300
C9A—H93A	1.0007	C11B—H14B	0.9834
C10A—C11A	1.524 (6)	C11B—H15B	0.9834
C10A—H12A	1.0007	C11B—H16B	0.9834
C10A—H13A	1.0007	N1C—H1C	0.857 (19)
C11A—H14A	0.9813	N1C—H2C	0.885 (19)
C11A—H15A	0.9813	N1C—H3C	0.869 (19)
C11A—H16A	0.9813	N1C—H4C	0.85 (2)
O1B—C6B	1.257 (4)	N1D—H1D	0.86 (2)
O2B—C12B	1.267 (4)	N1D—H2D	0.876 (19)
O3B—C12B	1.255 (4)	N1D—H3D	0.888 (19)
N1B—C1B	1.477 (5)	N1D—H4D	0.86 (2)
C1A—N1A—H1A	114 (3)	N1B—C1B—C6B	108.6 (3)
C1A—N1A—H2A	112 (3)	N1B—C1B—C2B	110.3 (3)
H1A—N1A—H2A	108 (4)	C6B—C1B—C2B	110.5 (3)
C6A—N2A—C7A	124.9 (3)	N1B—C1B—H11B	109.1
C6A—N2A—H4A	116 (3)	C6B—C1B—H11B	109.1
C7A—N2A—H4A	116 (3)	C2B—C1B—H11B	109.1
N1A—C1A—C6A	108.5 (3)	C3B—C2B—C1B	111.6 (3)
N1A—C1A—C2A	109.5 (3)	C3B—C2B—C4B	111.4 (3)
C6A—C1A—C2A	111.3 (3)	C1B—C2B—C4B	111.5 (3)
N1A—C1A—H11A	109.2	C3B—C2B—H21B	107.4
C6A—C1A—H11A	109.2	C1B—C2B—H21B	107.4
C2A—C1A—H11A	109.2	C4B—C2B—H21B	107.4
C3A—C2A—C1A	112.7 (3)	C2B—C3B—H31B	109.5
C3A—C2A—C4A	110.7 (4)	C2B—C3B—H32B	109.5
C1A—C2A—C4A	109.4 (4)	H31B—C3B—H32B	109.5
C3A—C2A—H21A	108.0	C2B—C3B—H33B	109.5
C1A—C2A—H21A	108.0	H31B—C3B—H33B	109.5
C4A—C2A—H21A	108.0	H32B—C3B—H33B	109.5
C2A—C3A—H31A	109.5	C5B—C4B—C2B	114.4 (4)
C2A—C3A—H32A	109.5	C5B—C4B—H41B	108.7
H31A—C3A—H32A	109.5	C2B—C4B—H41B	108.7
C2A—C3A—H33A	109.5	C5B—C4B—H42B	108.7
H31A—C3A—H33A	109.5	C2B—C4B—H42B	108.7
H32A—C3A—H33A	109.5	H41B—C4B—H42B	107.6
C5A—C4A—C2A	114.5 (5)	C4B—C5B—H51B	109.5
C5A—C4A—H41A	108.6	C4B—C5B—H52B	109.5
C2A—C4A—H41A	108.6	H51B—C5B—H52B	109.5
C5A—C4A—H42A	108.6	C4B—C5B—H53B	109.5
C2A—C4A—H42A	108.6	H51B—C5B—H53B	109.5
H41A—C4A—H42A	107.6	H52B—C5B—H53B	109.5
C4A—C5A—H51A	109.5	O1B—C6B—N2B	123.0 (3)
C4A—C5A—H52A	109.5	O1B—C6B—C1B	121.5 (3)
H51A—C5A—H52A	109.5	N2B—C6B—C1B	115.5 (4)
C4A—C5A—H53A	109.5	N2B—C7B—C12B	108.0 (3)
H51A—C5A—H53A	109.5	N2B—C7B—C8B	111.2 (3)
H52A—C5A—H53A	109.5	C12B—C7B—C8B	112.4 (3)
O1A—C6A—N2A	122.7 (4)	N2B—C7B—H71B	108.4
O1A—C6A—C1A	121.3 (4)	C12B—C7B—H71B	108.4
N2A—C6A—C1A	116.0 (3)	C8B—C7B—H71B	108.4
N2A—C7A—C12A	108.1 (3)	C9B—C8B—C10B	112.4 (3)
N2A—C7A—C8A	112.3 (3)	C9B—C8B—C7B	112.4 (3)
C12A—C7A—C8A	112.5 (3)	C10B—C8B—C7B	110.1 (3)
N2A—C7A—H71A	107.9	C9B—C8B—H81B	107.2
C12A—C7A—H71A	107.9	C10B—C8B—H81B	107.2
C8A—C7A—H71A	107.9	C7B—C8B—H81B	107.2
C10A—C8A—C9A	111.8 (3)	C8B—C9B—H91B	109.5
C10A—C8A—C7A	111.7 (3)	C8B—C9B—H92B	109.5
C9A—C8A—C7A	111.4 (3)	H91B—C9B—H92B	109.5
C10A—C8A—H81A	107.2	C8B—C9B—H93B	109.5
C9A—C8A—H81A	107.2	H91B—C9B—H93B	109.5
C7A—C8A—H81A	107.2	H92B—C9B—H93B	109.5
C8A—C9A—H91A	109.5	C11B—C10B—C8B	113.9 (3)
C8A—C9A—H92A	109.5	C11B—C10B—H12B	108.8
H91A—C9A—H92A	109.5	C8B—C10B—H12B	108.8
C8A—C9A—H93A	109.5	C11B—C10B—H13B	108.8
H91A—C9A—H93A	109.5	C8B—C10B—H13B	108.8
H92A—C9A—H93A	109.5	H12B—C10B—H13B	107.7
C11A—C10A—C8A	114.4 (3)	C10B—C11B—H14B	109.5
C11A—C10A—H12A	108.7	C10B—C11B—H15B	109.5
C8A—C10A—H12A	108.7	H14B—C11B—H15B	109.5
C11A—C10A—H13A	108.7	C10B—C11B—H16B	109.5
C8A—C10A—H13A	108.7	H14B—C11B—H16B	109.5
H12A—C10A—H13A	107.6	H15B—C11B—H16B	109.5
C10A—C11A—H14A	109.5	O3B—C12B—O2B	125.7 (3)
C10A—C11A—H15A	109.5	O3B—C12B—C7B	116.8 (3)
H14A—C11A—H15A	109.5	O2B—C12B—C7B	117.4 (3)
C10A—C11A—H16A	109.5	H1C—N1C—H2C	107 (4)
H14A—C11A—H16A	109.5	H1C—N1C—H3C	110 (4)
H15A—C11A—H16A	109.5	H2C—N1C—H3C	110 (4)
O3A—C12A—O2A	124.7 (3)	H1C—N1C—H4C	99 (4)
O3A—C12A—C7A	117.7 (3)	H2C—N1C—H4C	108 (4)
O2A—C12A—C7A	117.6 (3)	H3C—N1C—H4C	121 (4)
C1B—N1B—H1B	106 (3)	H1D—N1D—H2D	108 (4)
C1B—N1B—H2B	102 (3)	H1D—N1D—H3D	114 (4)
H1B—N1B—H2B	106 (4)	H2D—N1D—H3D	113 (4)
C6B—N2B—C7B	124.7 (3)	H1D—N1D—H4D	119 (4)
C6B—N2B—H4B	111 (4)	H2D—N1D—H4D	102 (4)
C7B—N2B—H4B	124 (4)	H3D—N1D—H4D	100 (4)
N1A—C1A—C2A—C3A	167.1 (4)	N1B—C1B—C2B—C3B	178.9 (3)
C6A—C1A—C2A—C3A	47.1 (5)	C6B—C1B—C2B—C3B	58.9 (4)
N1A—C1A—C2A—C4A	−69.4 (4)	N1B—C1B—C2B—C4B	−55.8 (4)
C6A—C1A—C2A—C4A	170.6 (4)	C6B—C1B—C2B—C4B	−175.9 (4)
C3A—C2A—C4A—C5A	−65.8 (6)	C3B—C2B—C4B—C5B	69.1 (5)
C1A—C2A—C4A—C5A	169.5 (4)	C1B—C2B—C4B—C5B	−56.3 (5)
C7A—N2A—C6A—O1A	−4.7 (6)	C7B—N2B—C6B—O1B	−3.0 (6)
C7A—N2A—C6A—C1A	175.3 (3)	C7B—N2B—C6B—C1B	177.8 (3)
N1A—C1A—C6A—O1A	148.0 (3)	N1B—C1B—C6B—O1B	145.5 (4)
C2A—C1A—C6A—O1A	−91.5 (4)	C2B—C1B—C6B—O1B	−93.4 (4)
N1A—C1A—C6A—N2A	−32.0 (4)	N1B—C1B—C6B—N2B	−35.2 (4)
C2A—C1A—C6A—N2A	88.5 (4)	C2B—C1B—C6B—N2B	85.9 (4)
C6A—N2A—C7A—C12A	−137.1 (4)	C6B—N2B—C7B—C12B	−138.9 (4)
C6A—N2A—C7A—C8A	98.2 (4)	C6B—N2B—C7B—C8B	97.4 (4)
N2A—C7A—C8A—C10A	−174.3 (3)	N2B—C7B—C8B—C9B	58.1 (4)
C12A—C7A—C8A—C10A	63.5 (4)	C12B—C7B—C8B—C9B	−63.0 (4)
N2A—C7A—C8A—C9A	59.9 (4)	N2B—C7B—C8B—C10B	−175.7 (3)
C12A—C7A—C8A—C9A	−62.3 (4)	C12B—C7B—C8B—C10B	63.1 (4)
C9A—C8A—C10A—C11A	−61.3 (5)	C9B—C8B—C10B—C11B	−64.9 (5)
C7A—C8A—C10A—C11A	173.1 (3)	C7B—C8B—C10B—C11B	169.0 (3)
N2A—C7A—C12A—O3A	151.4 (3)	N2B—C7B—C12B—O3B	151.3 (3)
C8A—C7A—C12A—O3A	−84.0 (4)	C8B—C7B—C12B—O3B	−85.7 (4)
N2A—C7A—C12A—O2A	−28.9 (5)	N2B—C7B—C12B—O2B	−29.2 (5)
C8A—C7A—C12A—O2A	95.7 (4)	C8B—C7B—C12B—O2B	93.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1B^i	0.93 (5)	2.40 (5)	3.323 (5)	174 (4)
N1A—H2A···O1A^i	0.89 (5)	2.56 (5)	3.410 (5)	162 (4)
N2A—H4A···O2A	0.85 (4)	2.26 (4)	2.666 (4)	109 (3)
N2A—H4A···N1A	0.85 (4)	2.27 (4)	2.698 (5)	112 (3)
N1B—H1B···O1A	0.93 (5)	2.43 (5)	3.318 (5)	158 (4)
N1B—H2B···O1B^i	0.85 (5)	2.68 (5)	3.451 (4)	153 (4)
N2B—H4B···O2B	0.73 (4)	2.44 (5)	2.681 (4)	102 (4)
N2B—H4B···N1B	0.73 (4)	2.28 (4)	2.700 (5)	118 (4)
N1C—H1C···O1A	0.86 (2)	2.01 (2)	2.862 (4)	173 (4)
N1C—H2C···O2B	0.88 (2)	1.89 (2)	2.768 (4)	174 (4)
N1C—H3C···O3A^ii	0.87 (2)	1.93 (2)	2.777 (4)	166 (4)
N1C—H4C···O3B^i	0.85 (2)	2.03 (2)	2.863 (4)	165 (4)
N1D—H1D···O1B	0.86 (2)	2.02 (2)	2.882 (4)	172 (4)
N1D—H2D···O2A^iii	0.88 (2)	1.93 (2)	2.779 (4)	164 (4)
N1D—H3D···O3B^iv	0.89 (2)	1.90 (2)	2.764 (4)	164 (4)
N1D—H4D···O3A	0.86 (2)	1.98 (2)	2.829 (4)	170 (4)

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