Variable-temperature neutron diffraction studies of the short, strong N...O hydrogen bonds in the 1:2 co-crystal of benzene-1,2,4,5-tetracarboxylic acid and 4,4'-bipyridyl

The 1:2 adduct of benzene-1,2,4,5-tetracarboxylic acid and 4,4′-bipyridyl at 100 K has been studied by single-crystal neutron diffraction at 20, 200 and 296 K. The structure contains two short, strong N...O hydrogen bonds: one O—H...N hydrogen bond [O...N 2.6104 (17) Å at 20 K] and one short N—H...O hydrogen bond [N...O 2.5220 (17) Å at 20 K]. The N—H distance in the N—H...O hydrogen bond changes from 1.207 (3) Å at 20 K to 1.302 (4) Å at 296 K and the N...O distance increases to 2.5315 (16) Å at 296 K. At 200 K the H atom lies in an intermediate position 1.251 (6) Å from the N atom with an N...O separation of 2.520 (4) Å. The O—H...N hydrogen bond, on the other hand, does not change with temperature.

Computing details

Data collection: MAD (Barthelemy, 1984) for hex20, hex296; LADI Control for hexladi; SMART (Bruker, 1998) for hex30x. Cell refinement: RAFD19 (Filhol, 1998) for hex20, hex296; LAUEGEN (Campbell) for hexladi; SAINT (Bruker, 1998) for hex30x. Data reduction: RETREAT (Wilkinson, et al. 1988) for hex20, hex296; INTEGRATE+ and LAUENORM (Wilkinson), (Campbell) for hexladi; SAINT (Bruker, 1998) for hex30x. Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) for hexladi, hex30x. For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

(hex20)

Crystal data

C30H22N4O8	Z = 1
Mr = 566.00	F(000) = 200.986
Triclinic, P1	Dx = 1.525 Mg m^−3
a = 7.3561 (2) Å	Neutron radiation, λ = 1.3102 Å
b = 9.5856 (2) Å	Cell parameters from 2325 reflections
c = 10.1478 (3) Å	θ = 5–55°
α = 65.203 (2)°	µ = 0.17 mm^−1
β = 72.699 (3)°	T = 20 K
γ = 77.099 (3)°	Prism, colourless
V = 616.16 (3) Å^3	4.5 × 1.2 × 0.75 mm

Data collection

D19 diffractometer	1743 reflections with I > 2σ(I)
Radiation source: ILL high flux reactor	Rint = 0.023
Germanium (115) monochromator	θmax = 56.3°, θmin = 4.2°
ω scans	h = −9→9
Absorption correction: gaussian D19ABS (Matthewmann et al, 1982)	k = −12→6
Tmin = 0.602, Tmax = 0.892	l = −12→12
2464 measured reflections	2 standard reflections every 75 reflections
1866 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: X-Ray structure
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.033	w = 1/[σ^2(Fo^2) + (0.0471P)^2 + 1.8319P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.086	(Δ/σ)max = 0.001
S = 1.16	Δρmax = 0.52 e Å^−3
1866 reflections	Δρmin = −0.57 e Å^−3
290 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0052 (5)

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
C1	0.58665 (19)	0.58090 (16)	−0.14904 (14)	0.0041 (3)
C10	0.6740 (2)	0.67889 (15)	−0.30727 (14)	0.0043 (3)
O11	0.6249 (2)	0.81769 (18)	−0.35625 (16)	0.0079 (3)
O12	0.8029 (2)	0.60369 (18)	−0.38215 (16)	0.0066 (3)
C2	0.39134 (19)	0.55951 (16)	−0.10856 (14)	0.0040 (3)
C20	0.2751 (2)	0.61852 (15)	−0.22570 (14)	0.0048 (3)
O21	0.1041 (2)	0.66784 (19)	−0.19595 (16)	0.0081 (3)
O22	0.3705 (2)	0.60894 (19)	−0.35073 (16)	0.0068 (3)
H2	0.8232 (4)	0.6725 (4)	−0.4988 (3)	0.0178 (6)
C3	0.3056 (2)	0.47917 (16)	0.04059 (14)	0.0050 (3)
H3	0.1545 (4)	0.4613 (4)	0.0721 (3)	0.0189 (6)
N1	0.28533 (14)	0.77383 (11)	−0.59816 (10)	0.0060 (2)
H1	0.3100 (5)	0.6951 (4)	−0.4746 (3)	0.0209 (6)
C11	0.3550 (2)	0.71661 (16)	−0.70593 (14)	0.0064 (3)
H11	0.4251 (5)	0.5982 (3)	−0.6727 (3)	0.0216 (7)
C12	0.3366 (2)	0.80495 (16)	−0.85091 (14)	0.0057 (3)
H12	0.3948 (5)	0.7518 (4)	−0.9329 (3)	0.0230 (7)
C13	0.24495 (19)	0.95648 (15)	−0.88721 (14)	0.0043 (3)
C14	0.1754 (2)	1.01320 (16)	−0.77242 (14)	0.0063 (3)
H14	0.1036 (5)	1.1303 (3)	−0.7911 (3)	0.0220 (7)
C15	0.1994 (2)	0.91871 (16)	−0.62992 (14)	0.0065 (3)
H15	0.1538 (5)	0.9598 (4)	−0.5390 (3)	0.0231 (7)
C21	0.2778 (2)	1.09077 (16)	−1.30061 (14)	0.0065 (3)
H21	0.3382 (5)	1.0512 (4)	−1.3925 (3)	0.0226 (7)
C22	0.3019 (2)	0.99816 (16)	−1.15745 (14)	0.0060 (3)
H22	0.3814 (5)	0.8852 (3)	−1.1410 (3)	0.0230 (7)
C23	0.22345 (19)	1.05375 (15)	−1.04229 (13)	0.0043 (3)
C24	0.1247 (2)	1.20336 (16)	−1.07930 (14)	0.0061 (3)
H24	0.0579 (5)	1.2542 (4)	−0.9957 (3)	0.0212 (7)
C25	0.1081 (2)	1.28894 (16)	−1.22600 (14)	0.0058 (3)
H25	0.0339 (5)	1.4057 (3)	−1.2582 (3)	0.0230 (7)
N2	0.18212 (14)	1.23369 (11)	−1.33506 (10)	0.0061 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0053 (6)	0.0034 (6)	0.0037 (5)	−0.0012 (5)	−0.0016 (5)	−0.0008 (5)
C10	0.0060 (6)	0.0031 (6)	0.0033 (5)	−0.0033 (6)	0.0005 (5)	−0.0004 (5)
O11	0.0121 (7)	0.0038 (7)	0.0060 (6)	−0.0006 (7)	−0.0002 (6)	−0.0015 (6)
O12	0.0073 (7)	0.0048 (7)	0.0057 (7)	−0.0005 (7)	0.0003 (6)	−0.0015 (6)
C2	0.0043 (6)	0.0042 (6)	0.0040 (6)	−0.0010 (5)	−0.0016 (5)	−0.0013 (5)
C20	0.0060 (6)	0.0044 (6)	0.0045 (5)	0.0003 (6)	−0.0017 (5)	−0.0023 (5)
O21	0.0066 (7)	0.0105 (8)	0.0080 (6)	0.0010 (7)	−0.0024 (6)	−0.0049 (6)
O22	0.0078 (7)	0.0078 (7)	0.0047 (6)	0.0014 (7)	−0.0023 (6)	−0.0029 (6)
H2	0.0165 (13)	0.0187 (14)	0.0171 (14)	−0.0033 (13)	−0.0002 (11)	−0.0077 (13)
C3	0.0053 (6)	0.0062 (6)	0.0037 (6)	−0.0018 (6)	−0.0008 (5)	−0.0016 (5)
H3	0.0101 (13)	0.0271 (16)	0.0175 (12)	−0.0067 (13)	−0.0032 (11)	−0.0044 (12)
N1	0.0073 (4)	0.0056 (5)	0.0057 (4)	−0.0004 (4)	−0.0023 (4)	−0.0024 (4)
H1	0.0214 (15)	0.0212 (16)	0.0241 (15)	−0.0026 (14)	−0.0051 (12)	−0.0124 (13)
C11	0.0090 (7)	0.0045 (7)	0.0056 (6)	−0.0005 (6)	−0.0016 (5)	−0.0020 (5)
H11	0.0314 (17)	0.0133 (15)	0.0197 (13)	0.0045 (14)	−0.0099 (13)	−0.0066 (12)
C12	0.0089 (7)	0.0037 (6)	0.0050 (6)	0.0012 (6)	−0.0025 (5)	−0.0023 (5)
H12	0.0350 (18)	0.0186 (14)	0.0175 (13)	0.0069 (14)	−0.0087 (13)	−0.0121 (12)
C13	0.0050 (6)	0.0038 (6)	0.0044 (6)	0.0001 (5)	−0.0015 (5)	−0.0018 (5)
C14	0.0097 (6)	0.0035 (7)	0.0053 (6)	0.0023 (6)	−0.0023 (5)	−0.0025 (5)
H14	0.0330 (17)	0.0114 (14)	0.0207 (13)	0.0064 (14)	−0.0081 (13)	−0.0084 (12)
C15	0.0094 (6)	0.0059 (7)	0.0049 (6)	0.0014 (6)	−0.0031 (5)	−0.0030 (5)
H15	0.0345 (18)	0.0234 (15)	0.0148 (12)	0.0031 (15)	−0.0078 (12)	−0.0121 (12)
C21	0.0101 (6)	0.0053 (7)	0.0041 (6)	0.0002 (6)	−0.0017 (5)	−0.0024 (5)
H21	0.0332 (17)	0.0198 (15)	0.0145 (13)	0.0059 (14)	−0.0048 (13)	−0.0111 (12)
C22	0.0087 (7)	0.0044 (7)	0.0046 (6)	0.0012 (6)	−0.0014 (5)	−0.0024 (5)
H22	0.0333 (18)	0.0131 (15)	0.0193 (13)	0.0076 (14)	−0.0076 (13)	−0.0070 (12)
C23	0.0059 (6)	0.0037 (7)	0.0040 (6)	−0.0003 (6)	−0.0006 (5)	−0.0025 (5)
C24	0.0090 (6)	0.0043 (6)	0.0050 (6)	0.0009 (6)	−0.0020 (5)	−0.0023 (5)
H24	0.0301 (16)	0.0187 (15)	0.0165 (13)	0.0052 (14)	−0.0057 (12)	−0.0122 (12)
C25	0.0073 (6)	0.0039 (7)	0.0054 (6)	−0.0012 (6)	−0.0002 (5)	−0.0015 (5)
H25	0.0326 (18)	0.0137 (15)	0.0218 (13)	0.0065 (15)	−0.0104 (13)	−0.0077 (12)
N2	0.0078 (5)	0.0064 (5)	0.0041 (4)	−0.0006 (4)	−0.0014 (4)	−0.0020 (4)

Geometric parameters (Å, º)

C1—C3^i	1.3978 (19)	C12—C13	1.4007 (18)
C1—C2	1.409 (2)	C12—H12	1.087 (3)
C1—C10	1.5047 (17)	C13—C14	1.4024 (17)
C10—O11	1.219 (2)	C13—C23	1.4907 (18)
C10—O12	1.312 (2)	C14—C15	1.3873 (18)
O12—H2	1.069 (3)	C14—H14	1.091 (3)
C2—C3	1.3975 (17)	C15—H15	1.086 (3)
C2—C20	1.5131 (18)	C21—N2	1.3449 (16)
C20—O21	1.235 (2)	C21—C22	1.3895 (18)
C20—O22	1.2845 (19)	C21—H21	1.088 (3)
O22—H1	1.325 (3)	C22—C23	1.4023 (17)
C3—C1^i	1.3978 (19)	C22—H22	1.080 (3)
C3—H3	1.093 (3)	C23—C24	1.4039 (19)
N1—C15	1.3364 (16)	C24—C25	1.3939 (18)
N1—C11	1.3431 (15)	C24—H24	1.091 (3)
N1—H1	1.207 (3)	C25—N2	1.3440 (15)
C11—C12	1.3865 (18)	C25—H25	1.088 (3)
C11—H11	1.090 (3)
C3^i—C1—C2	120.08 (12)	C12—C13—C14	117.47 (11)
C3^i—C1—C10	120.33 (12)	C12—C13—C23	121.12 (11)
C2—C1—C10	119.43 (12)	C14—C13—C23	121.41 (11)
O11—C10—O12	124.96 (14)	C15—C14—C13	119.39 (12)
O11—C10—C1	119.99 (12)	C15—C14—H14	118.29 (19)
O12—C10—C1	115.05 (12)	C13—C14—H14	122.3 (2)
C10—O12—H2	109.2 (2)	N1—C15—C14	121.81 (11)
C3—C2—C1	119.68 (12)	N1—C15—H15	116.3 (2)
C3—C2—C20	119.68 (12)	C14—C15—H15	121.8 (2)
C1—C2—C20	120.61 (12)	N2—C21—C22	122.81 (11)
O21—C20—O22	126.11 (15)	N2—C21—H21	116.0 (2)
O21—C20—C2	120.17 (12)	C22—C21—H21	121.2 (2)
O22—C20—C2	113.71 (12)	C21—C22—C23	119.51 (12)
C20—O22—H1	120.32 (18)	C21—C22—H22	117.3 (2)
C2—C3—C1^i	120.24 (13)	C23—C22—H22	123.2 (2)
C2—C3—H3	119.81 (19)	C22—C23—C24	117.34 (11)
C1^i—C3—H3	119.9 (2)	C22—C23—C13	120.78 (11)
C15—N1—C11	120.22 (10)	C24—C23—C13	121.88 (11)
C15—N1—H1	120.78 (16)	C25—C24—C23	119.47 (12)
C11—N1—H1	118.89 (17)	C25—C24—H24	118.8 (2)
N1—C11—C12	120.97 (12)	C23—C24—H24	121.7 (2)
N1—C11—H11	116.42 (19)	N2—C25—C24	122.62 (12)
C12—C11—H11	122.61 (19)	N2—C25—H25	116.29 (19)
C11—C12—C13	120.12 (12)	C24—C25—H25	121.1 (2)
C11—C12—H12	117.5 (2)	C25—N2—C21	118.24 (10)
C13—C12—H12	122.4 (2)

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
N1—H1···O22	1.206 (3)	1.325 (3)	2.5217 (18)	169.6 (3)
O12—H2···N2^ii	1.068 (3)	1.551 (3)	2.6103 (17)	170.1 (3)

Symmetry code: (ii) −x+1, −y+2, −z−2.

(hex296)

Crystal data

C30H22N4O8	Z = 1
Mr = 566.00	F(000) = 200.986
Triclinic, P1	Dx = 1.478 Mg m^−3
a = 7.5011 (2) Å	Neutron radiation, λ = 1.302 Å
b = 9.7868 (3) Å	Cell parameters from 2509 reflections
c = 10.2303 (3) Å	θ = 3–55°
α = 64.140 (3)°	µ = 0.17 mm^−1
β = 71.682 (3)°	T = 293 K
γ = 75.516 (3)°	Prism, colourless
V = 635.93 (4) Å^3	4.5 × 1.2 × 0.75 mm

Data collection

D19 diffractometer	1894 reflections with I > 2σ(I)
Radiation source: ILL High flux reactor	Rint = 0.028
Germanium (115) monochromator	θmax = 55.5°, θmin = 4.2°
ω scans	h = −9→9
Absorption correction: gaussian D19ABS (Matthewmann et al, 1982)	k = −12→4
Tmin = 0.602, Tmax = 0.892	l = −12→12
2914 measured reflections	2 standard reflections every 70 reflections
2145 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: X-Ray Structure
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0417P)^2 + 1.6198P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.088	(Δ/σ)max = 0.023
S = 1.05	Δρmax = 0.43 e Å^−3
2145 reflections	Δρmin = −0.43 e Å^−3
291 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0066 (6)

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
C1	0.41579 (17)	0.41855 (14)	0.14981 (13)	0.0252 (3)
C10	0.3285 (2)	0.32047 (15)	0.30805 (13)	0.0293 (3)
O11	0.3785 (4)	0.1839 (2)	0.3567 (2)	0.0530 (6)
O12	0.1992 (2)	0.3939 (2)	0.38196 (17)	0.0367 (4)
H2	0.1780 (4)	0.3249 (4)	0.4998 (4)	0.0509 (7)
C2	0.60671 (17)	0.44024 (14)	0.10818 (13)	0.0242 (3)
C20	0.72238 (18)	0.38061 (15)	0.22366 (14)	0.0282 (3)
O21	0.8909 (2)	0.3350 (3)	0.1937 (2)	0.0492 (5)
O22	0.6282 (3)	0.3887 (2)	0.34904 (18)	0.0434 (5)
C3	0.69031 (18)	0.52122 (15)	−0.04139 (13)	0.0264 (3)
H3	0.8373 (4)	0.5392 (4)	−0.0727 (3)	0.0475 (7)
N1	0.28131 (15)	−0.22432 (12)	1.40422 (11)	0.0353 (3)
H1	0.3116 (5)	−0.3078 (4)	1.5369 (4)	0.0581 (8)
C11	0.2025 (3)	−0.07861 (19)	1.36857 (17)	0.0447 (4)
H11	0.1600 (9)	−0.0374 (6)	1.4578 (4)	0.0912 (17)
C12	0.1801 (2)	0.01558 (18)	1.22540 (16)	0.0416 (4)
H12	0.1126 (8)	0.1331 (5)	1.2044 (4)	0.0844 (16)
C13	0.24339 (17)	−0.04221 (15)	1.11355 (13)	0.0258 (3)
C14	0.3280 (2)	−0.19436 (17)	1.15343 (16)	0.0382 (4)
H14	0.3815 (9)	−0.2474 (5)	1.0734 (4)	0.0869 (17)
C15	0.3450 (3)	−0.28168 (17)	1.29888 (17)	0.0406 (4)
H15	0.4098 (8)	−0.4002 (4)	1.3334 (4)	0.0782 (13)
C21	0.1128 (2)	0.28835 (17)	0.77215 (15)	0.0371 (3)
H21	0.0405 (7)	0.4055 (4)	0.7373 (4)	0.0692 (11)
C22	0.1290 (2)	0.20355 (16)	0.91907 (15)	0.0345 (3)
H22	0.0651 (6)	0.2552 (4)	1.0004 (4)	0.0656 (11)
C23	0.22317 (17)	0.05442 (14)	0.95848 (13)	0.0260 (3)
C24	0.2977 (2)	−0.00191 (17)	0.84542 (15)	0.0378 (4)
H24	0.3755 (7)	−0.1154 (4)	0.8643 (4)	0.0758 (13)
C25	0.2749 (2)	0.08987 (18)	0.70220 (15)	0.0405 (4)
H25	0.3339 (7)	0.0500 (5)	0.6118 (4)	0.0744 (13)
N2	0.18361 (15)	0.23219 (12)	0.66549 (10)	0.0357 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0312 (6)	0.0272 (6)	0.0131 (5)	−0.0036 (5)	−0.0054 (5)	−0.0041 (5)
C10	0.0405 (7)	0.0266 (6)	0.0142 (6)	−0.0040 (6)	−0.0046 (5)	−0.0035 (5)
O11	0.0898 (15)	0.0269 (8)	0.0235 (8)	−0.0048 (10)	0.0010 (9)	−0.0045 (7)
O12	0.0373 (8)	0.0392 (8)	0.0196 (7)	0.0039 (7)	−0.0036 (6)	−0.0058 (7)
H2	0.0447 (14)	0.0540 (18)	0.0445 (18)	−0.0038 (14)	0.0006 (13)	−0.0196 (16)
C2	0.0298 (6)	0.0263 (6)	0.0135 (5)	−0.0011 (5)	−0.0077 (5)	−0.0047 (5)
C20	0.0331 (6)	0.0296 (6)	0.0185 (6)	0.0053 (5)	−0.0116 (5)	−0.0076 (5)
O21	0.0350 (8)	0.0752 (14)	0.0355 (9)	0.0126 (9)	−0.0164 (7)	−0.0249 (10)
O22	0.0473 (9)	0.0565 (11)	0.0218 (7)	0.0154 (8)	−0.0175 (7)	−0.0165 (8)
C3	0.0298 (6)	0.0306 (6)	0.0145 (5)	−0.0035 (5)	−0.0065 (5)	−0.0043 (5)
H3	0.0377 (14)	0.0612 (18)	0.0346 (14)	−0.0110 (13)	−0.0054 (11)	−0.0104 (14)
N1	0.0441 (5)	0.0375 (5)	0.0221 (4)	−0.0003 (5)	−0.0156 (4)	−0.0070 (4)
H1	0.0549 (17)	0.064 (2)	0.060 (2)	−0.0034 (16)	−0.0143 (16)	−0.0301 (19)
C11	0.0638 (10)	0.0438 (9)	0.0248 (7)	0.0114 (8)	−0.0191 (7)	−0.0157 (7)
H11	0.148 (4)	0.081 (3)	0.045 (2)	0.037 (3)	−0.043 (2)	−0.038 (2)
C12	0.0618 (9)	0.0355 (8)	0.0245 (7)	0.0136 (7)	−0.0189 (7)	−0.0137 (6)
H12	0.145 (4)	0.051 (2)	0.051 (2)	0.040 (2)	−0.046 (2)	−0.0277 (18)
C13	0.0312 (6)	0.0265 (6)	0.0181 (6)	−0.0007 (5)	−0.0089 (5)	−0.0067 (5)
C14	0.0601 (9)	0.0284 (7)	0.0247 (7)	0.0062 (7)	−0.0181 (7)	−0.0098 (6)
H14	0.162 (5)	0.0503 (19)	0.0427 (18)	0.032 (3)	−0.042 (2)	−0.0249 (17)
C15	0.0627 (9)	0.0301 (8)	0.0257 (7)	0.0034 (7)	−0.0201 (7)	−0.0063 (6)
H15	0.135 (4)	0.0414 (19)	0.0497 (19)	0.017 (2)	−0.045 (2)	−0.0101 (16)
C21	0.0435 (7)	0.0330 (8)	0.0216 (6)	0.0058 (7)	−0.0090 (6)	−0.0038 (6)
H21	0.096 (3)	0.0454 (19)	0.0443 (17)	0.027 (2)	−0.0251 (19)	−0.0114 (16)
C22	0.0439 (7)	0.0314 (7)	0.0216 (6)	0.0055 (6)	−0.0110 (6)	−0.0078 (6)
H22	0.102 (3)	0.0486 (17)	0.0371 (16)	0.0215 (19)	−0.0218 (18)	−0.0211 (15)
C23	0.0316 (6)	0.0260 (6)	0.0178 (6)	0.0005 (5)	−0.0084 (5)	−0.0068 (5)
C24	0.0543 (8)	0.0321 (8)	0.0194 (6)	0.0040 (7)	−0.0088 (6)	−0.0083 (6)
H24	0.123 (3)	0.0470 (19)	0.0419 (18)	0.030 (2)	−0.027 (2)	−0.0197 (16)
C25	0.0571 (9)	0.0388 (8)	0.0184 (6)	0.0030 (7)	−0.0100 (6)	−0.0089 (6)
H25	0.116 (3)	0.067 (2)	0.0290 (15)	0.015 (2)	−0.0186 (19)	−0.0227 (16)
N2	0.0413 (5)	0.0381 (5)	0.0177 (4)	−0.0008 (5)	−0.0069 (4)	−0.0043 (4)

Geometric parameters (Å, º)

C1—C3^i	1.4003 (18)	C12—C13	1.394 (2)
C1—C2	1.4026 (19)	C12—H12	1.089 (4)
C1—C10	1.505 (2)	C13—C14	1.395 (2)
C10—O11	1.209 (2)	C13—C23	1.485 (2)
C10—O12	1.301 (2)	C14—C15	1.384 (2)
O12—H2	1.076 (4)	C14—H14	1.077 (4)
C2—C3	1.3966 (19)	C15—H15	1.084 (4)
C2—C20	1.5095 (18)	C21—N2	1.3370 (19)
C20—O21	1.219 (2)	C21—C22	1.392 (2)
C20—O22	1.281 (2)	C21—H21	1.090 (4)
C3—C1^i	1.4003 (18)	C22—C23	1.393 (2)
C3—H3	1.084 (3)	C22—H22	1.083 (4)
N1—C15	1.332 (2)	C23—C24	1.396 (2)
N1—C11	1.333 (2)	C24—C25	1.384 (2)
N1—H1	1.302 (4)	C24—H24	1.082 (4)
C11—C12	1.386 (2)	C25—N2	1.334 (2)
C11—H11	1.082 (4)	C25—H25	1.083 (4)
C3^i—C1—C2	119.87 (12)	C12—C13—C14	117.07 (13)
C3^i—C1—C10	119.63 (12)	C12—C13—C23	121.43 (12)
C2—C1—C10	120.32 (11)	C14—C13—C23	121.49 (12)
O11—C10—O12	125.08 (17)	C15—C14—C13	120.21 (14)
O11—C10—C1	119.94 (15)	C15—C14—H14	118.1 (2)
O12—C10—C1	114.98 (13)	C13—C14—H14	121.7 (2)
C10—O12—H2	109.5 (2)	N1—C15—C14	121.57 (14)
C3—C2—C1	119.80 (11)	N1—C15—H15	116.4 (2)
C3—C2—C20	119.32 (12)	C14—C15—H15	122.0 (3)
C1—C2—C20	120.86 (11)	N2—C21—C22	122.58 (13)
O21—C20—O22	125.25 (15)	N2—C21—H21	115.9 (2)
O21—C20—C2	120.99 (14)	C22—C21—H21	121.6 (2)
O22—C20—C2	113.72 (13)	C21—C22—C23	119.60 (14)
C2—C3—C1^i	120.32 (12)	C21—C22—H22	118.7 (2)
C2—C3—H3	119.52 (19)	C23—C22—H22	121.7 (2)
C1^i—C3—H3	120.1 (2)	C22—C23—C24	117.07 (12)
C15—N1—C11	119.41 (12)	C22—C23—C13	122.10 (12)
C15—N1—H1	119.20 (19)	C24—C23—C13	120.83 (12)
C11—N1—H1	121.13 (19)	C25—C24—C23	119.68 (13)
N1—C11—C12	122.23 (14)	C25—C24—H24	117.7 (2)
N1—C11—H11	115.8 (3)	C23—C24—H24	122.7 (2)
C12—C11—H11	122.0 (3)	N2—C25—C24	122.93 (14)
C11—C12—C13	119.48 (14)	N2—C25—H25	115.8 (2)
C11—C12—H12	118.4 (2)	C24—C25—H25	121.2 (3)
C13—C12—H12	122.1 (2)	C25—N2—C21	118.15 (12)

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
N1—H1···O22^ii	1.301 (4)	1.240 (4)	2.531 (3)	169.4 (3)
O12—H2···N2	1.076 (4)	1.543 (4)	2.608 (3)	169.5 (3)

Symmetry code: (ii) −x+1, −y, −z+2.

(hexladi)

Crystal data

C30H22N4O8	V = 635.9 (5) Å^3
Mr = 566.00	Z = 1
Triclinic, P1	F(000) = 201
a = 7.541 (1) Å	Dx = 1.478 Mg m^−3
b = 9.715 (1) Å	Neutron radiation, λ = 1.1 to 1.9 Å
c = 10.204 (1) Å	µ = 0.00 mm^−1
α = 64.51 (1)°	T = 200 K
β = 72.03 (1)°	Plate, colourless
γ = 76.08 (1)°	1.3 × 0.6 × 0.2 mm

Data collection

LADI Laue diffractometer	1192 reflections with I > 2σ(I)
Radiation source: ILL high flux reactor	Rint = 0.113
Graphite monochromator	θmax = 30.7°, θmin = 3.2°
Laue method scans	h = −7→7
1961 measured reflections	k = −12→13
1961 independent reflections	l = 0→14

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: difference Fourier map
wR(F^2) = 0.125	All H-atom parameters refined
S = 1.28	w = 1/[σ^2(Fo^2) + (0.050P)^2] where P = (Fo^2 + 2Fc^2)/3
1961 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.71 e Å^−3
0 restraints	Δρmin = −0.75 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
N1	0.2833 (3)	−0.2257 (2)	1.40362 (18)	0.0241 (8)
H1	0.3112 (10)	−0.3049 (7)	1.5310 (7)	0.040 (2)
C11	0.3482 (5)	−0.2825 (3)	1.2972 (3)	0.0263 (11)
H11	0.4182 (12)	−0.3988 (6)	1.3279 (7)	0.052 (3)
C12	0.3314 (5)	−0.1950 (3)	1.1524 (2)	0.0263 (10)
H12	0.3858 (13)	−0.2476 (7)	1.0715 (6)	0.063 (3)
C13	0.2439 (4)	−0.0427 (3)	1.1136 (2)	0.0156 (9)
C14	0.1779 (5)	0.0143 (3)	1.2266 (2)	0.0290 (11)
H14	0.1083 (12)	0.1306 (7)	1.2078 (6)	0.057 (3)
C15	0.2001 (5)	−0.0801 (3)	1.3691 (3)	0.0303 (12)
H15	0.1555 (13)	−0.0405 (8)	1.4585 (6)	0.065 (3)
C21	0.2757 (5)	0.0899 (3)	0.7012 (3)	0.0278 (11)
H21	0.3353 (11)	0.0490 (7)	0.6103 (6)	0.047 (2)
C22	0.2985 (5)	−0.0020 (3)	0.8441 (2)	0.0237 (10)
H22	0.3791 (11)	−0.1135 (7)	0.8629 (6)	0.053 (3)
C23	0.2240 (4)	0.0544 (3)	0.9585 (2)	0.0182 (10)
C24	0.1266 (5)	0.2036 (3)	0.9205 (2)	0.0244 (10)
H24	0.0626 (12)	0.2548 (6)	1.0017 (6)	0.047 (2)
C25	0.1108 (5)	0.2893 (3)	0.7726 (2)	0.0230 (10)
H25	0.0379 (10)	0.4051 (6)	0.7397 (6)	0.049 (2)
N2	0.1829 (3)	0.2332 (2)	0.66540 (17)	0.0246 (8)
C1	0.5845 (5)	−0.4190 (3)	1.8510 (2)	0.0179 (10)
C10	0.6712 (5)	−0.3215 (3)	1.6921 (2)	0.0202 (10)
O11	0.6213 (6)	−0.1824 (3)	1.6424 (3)	0.0376 (14)
O12	0.8030 (5)	−0.3952 (3)	1.6176 (3)	0.0243 (12)
H2	0.8212 (10)	−0.3257 (7)	1.5017 (5)	0.046 (2)
C2	0.3934 (5)	−0.4405 (3)	1.8915 (2)	0.0173 (10)
C20	0.2775 (5)	−0.3806 (3)	1.7755 (2)	0.0199 (10)
O21	0.1074 (6)	−0.3335 (4)	1.8049 (3)	0.0320 (13)
O22	0.3708 (6)	−0.3895 (4)	1.6504 (3)	0.0239 (12)
C3	0.3082 (6)	−0.5211 (3)	2.0408 (2)	0.0187 (12)
H3	0.1592 (13)	−0.5402 (7)	2.0733 (7)	0.034 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0271 (17)	0.0294 (9)	0.0156 (7)	−0.0007 (10)	−0.0117 (8)	−0.0056 (6)
H1	0.035 (5)	0.044 (3)	0.045 (3)	−0.008 (3)	−0.008 (3)	−0.020 (3)
C11	0.036 (3)	0.0241 (13)	0.0193 (11)	0.0030 (14)	−0.0154 (12)	−0.0062 (9)
H11	0.090 (7)	0.025 (2)	0.045 (3)	0.014 (3)	−0.040 (4)	−0.012 (2)
C12	0.040 (3)	0.0215 (11)	0.0159 (10)	0.0054 (14)	−0.0129 (11)	−0.0064 (9)
H12	0.104 (7)	0.040 (3)	0.031 (3)	0.019 (4)	−0.016 (3)	−0.016 (2)
C13	0.017 (2)	0.0184 (10)	0.0119 (9)	−0.0019 (12)	−0.0072 (10)	−0.0042 (8)
C14	0.042 (3)	0.0274 (13)	0.0162 (10)	0.0104 (14)	−0.0141 (12)	−0.0106 (9)
H14	0.097 (7)	0.038 (3)	0.034 (3)	0.026 (4)	−0.033 (3)	−0.018 (2)
C15	0.041 (3)	0.0319 (14)	0.0172 (11)	0.0097 (15)	−0.0145 (12)	−0.0113 (10)
H15	0.102 (7)	0.062 (4)	0.029 (3)	0.022 (4)	−0.027 (3)	−0.025 (3)
C21	0.035 (2)	0.0296 (13)	0.0136 (10)	0.0000 (14)	−0.0053 (11)	−0.0069 (9)
H21	0.066 (6)	0.049 (3)	0.026 (2)	0.006 (3)	−0.014 (3)	−0.022 (2)
C22	0.028 (2)	0.0269 (13)	0.0152 (10)	0.0028 (14)	−0.0102 (11)	−0.0076 (9)
H22	0.075 (6)	0.042 (3)	0.035 (3)	0.017 (4)	−0.019 (3)	−0.019 (2)
C23	0.019 (2)	0.0194 (11)	0.0128 (9)	−0.0030 (13)	−0.0034 (10)	−0.0036 (8)
C24	0.031 (2)	0.0222 (12)	0.0154 (10)	0.0033 (13)	−0.0067 (11)	−0.0060 (9)
H24	0.073 (6)	0.036 (3)	0.029 (2)	0.012 (3)	−0.015 (3)	−0.019 (2)
C25	0.025 (2)	0.0245 (12)	0.0166 (10)	0.0016 (13)	−0.0094 (11)	−0.0045 (9)
H25	0.054 (5)	0.036 (3)	0.040 (3)	0.020 (3)	−0.023 (3)	−0.004 (2)
N2	0.0264 (17)	0.0295 (9)	0.0128 (7)	0.0003 (10)	−0.0060 (8)	−0.0047 (6)
C1	0.018 (2)	0.0236 (12)	0.0099 (9)	−0.0011 (13)	−0.0049 (11)	−0.0039 (8)
C10	0.024 (2)	0.0231 (12)	0.0119 (9)	−0.0042 (13)	−0.0051 (10)	−0.0039 (8)
O11	0.061 (3)	0.0206 (14)	0.0174 (12)	−0.0034 (17)	0.0018 (15)	−0.0041 (10)
O12	0.021 (3)	0.0284 (15)	0.0165 (12)	−0.0002 (16)	−0.0034 (13)	−0.0053 (11)
H2	0.046 (5)	0.048 (3)	0.030 (3)	0.003 (3)	0.000 (3)	−0.013 (2)
C2	0.023 (3)	0.0201 (11)	0.0104 (9)	−0.0025 (13)	−0.0074 (11)	−0.0048 (8)
C20	0.020 (2)	0.0247 (12)	0.0148 (10)	0.0027 (13)	−0.0098 (11)	−0.0070 (9)
O21	0.019 (3)	0.053 (2)	0.0252 (14)	0.0061 (19)	−0.0135 (14)	−0.0164 (13)
O22	0.023 (3)	0.0371 (16)	0.0166 (11)	0.0032 (16)	−0.0147 (13)	−0.0117 (11)
C3	0.020 (3)	0.0224 (12)	0.0109 (10)	−0.0061 (15)	−0.0033 (12)	−0.0030 (8)
H3	0.016 (6)	0.055 (4)	0.036 (3)	−0.008 (4)	−0.011 (3)	−0.015 (3)

Geometric parameters (Å, º)

N1—C11	1.338 (3)	C24—C25	1.401 (3)
N1—C15	1.341 (3)	C24—H24	1.079 (5)
N1—H1	1.246 (6)	C25—N2	1.342 (3)
C11—C12	1.379 (3)	C25—H25	1.082 (5)
C11—H11	1.078 (5)	C1—C2	1.404 (5)
C12—C13	1.403 (3)	C1—C3^i	1.406 (5)
C12—H12	1.083 (6)	C1—C10	1.506 (3)
C13—C14	1.399 (3)	C10—O11	1.230 (4)
C13—C23	1.485 (3)	C10—O12	1.315 (3)
C14—C15	1.382 (3)	O12—H2	1.062 (6)
C14—H14	1.086 (5)	C2—C3	1.396 (3)
C15—H15	1.072 (6)	C2—C20	1.515 (4)
C21—N2	1.345 (3)	C20—O21	1.232 (5)
C21—C22	1.381 (3)	C20—O22	1.281 (4)
C21—H21	1.095 (5)	O22—H1	1.285 (7)
C22—C23	1.409 (3)	C3—C1^i	1.406 (5)
C22—H22	1.074 (5)	C3—H3	1.101 (13)
C23—C24	1.402 (3)
C11—N1—C15	119.48 (19)	C22—C23—C13	120.93 (18)
C11—N1—H1	119.8 (3)	C25—C24—C23	119.2 (2)
C15—N1—H1	120.5 (3)	C25—C24—H24	118.6 (3)
N1—C11—C12	121.6 (2)	C23—C24—H24	122.1 (3)
N1—C11—H11	117.6 (4)	N2—C25—C24	122.4 (2)
C12—C11—H11	120.8 (4)	N2—C25—H25	116.7 (4)
C11—C12—C13	120.1 (2)	C24—C25—H25	120.9 (4)
C11—C12—H12	118.1 (3)	C25—N2—C21	118.64 (18)
C13—C12—H12	121.8 (3)	C2—C1—C3^i	120.6 (2)
C14—C13—C12	117.3 (2)	C2—C1—C10	119.6 (2)
C14—C13—C23	121.42 (19)	C3^i—C1—C10	119.6 (3)
C12—C13—C23	121.30 (19)	O11—C10—O12	124.7 (3)
C15—C14—C13	119.4 (2)	O11—C10—C1	120.0 (2)
C15—C14—H14	117.8 (4)	O12—C10—C1	115.3 (2)
C13—C14—H14	122.8 (3)	C10—O12—H2	108.2 (4)
N1—C15—C14	122.2 (2)	C3—C2—C1	119.9 (3)
N1—C15—H15	115.8 (4)	C3—C2—C20	118.8 (3)
C14—C15—H15	122.0 (4)	C1—C2—C20	121.2 (2)
N2—C21—C22	122.6 (2)	O21—C20—O22	124.7 (3)
N2—C21—H21	116.5 (4)	O21—C20—C2	121.2 (2)
C22—C21—H21	120.9 (4)	O22—C20—C2	114.0 (3)
C21—C22—C23	119.8 (2)	C20—O22—H1	120.2 (4)
C21—C22—H22	118.2 (4)	C2—C3—C1^i	119.5 (4)
C23—C22—H22	122.0 (4)	C2—C3—H3	120.4 (4)
C24—C23—C22	117.3 (2)	C1^i—C3—H3	120.1 (4)
C24—C23—C13	121.77 (19)

Symmetry code: (i) −x+1, −y−1, −z+4.

(hex30x)

Crystal data

C30H22N4O8	Z = 1
Mr = 566.52	F(000) = 294
Triclinic, P1	Dx = 1.526 Mg m^−3
a = 7.357 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.587 (3) Å	Cell parameters from 1690 reflections
c = 10.147 (3) Å	θ = 12.0–27.7°
α = 65.256 (4)°	µ = 0.11 mm^−1
β = 72.687 (4)°	T = 30 K
γ = 77.052 (4)°	Block, colourless
V = 616.4 (3) Å^3	0.5 × 0.35 × 0.15 mm

Data collection

Bruker SMART-CCD diffractometer	2126 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 27.6°, θmin = 2.3°
ω scans	h = −9→9
5958 measured reflections	k = −12→12
2549 independent reflections	l = −12→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	All H-atom parameters refined
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.030P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.66	(Δ/σ)max < 0.001
2549 reflections	Δρmax = 0.35 e Å^−3
235 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: 0.013 (3)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.58628 (18)	0.58045 (14)	−0.14876 (13)	0.0110 (3)
C10	0.67364 (18)	0.67962 (15)	−0.30729 (14)	0.0110 (3)
O11	0.62539 (13)	0.81828 (10)	−0.35663 (10)	0.0142 (2)
O12	0.80279 (12)	0.60285 (10)	−0.38178 (10)	0.0126 (2)
C2	0.39158 (18)	0.55949 (14)	−0.10827 (14)	0.0115 (3)
C20	0.27494 (18)	0.61849 (14)	−0.22590 (14)	0.0113 (3)
O21	0.10389 (13)	0.66758 (10)	−0.19559 (10)	0.0142 (2)
O22	0.37066 (13)	0.60893 (10)	−0.35071 (9)	0.0135 (2)
H2	0.820 (3)	0.666 (2)	−0.490 (2)	0.063 (7)*
C3	0.30654 (19)	0.47936 (14)	0.04044 (14)	0.0112 (3)
H3	0.174 (2)	0.4655 (16)	0.0667 (16)	0.012 (4)*
N1	0.28515 (15)	0.77398 (12)	−0.59822 (12)	0.0119 (2)
H1	0.309 (3)	0.702 (2)	−0.481 (2)	0.057 (6)*
C11	0.35504 (18)	0.71648 (15)	−0.70591 (14)	0.0126 (3)
H11	0.421 (2)	0.6135 (17)	−0.6806 (16)	0.010 (3)*
C12	0.33640 (18)	0.80494 (15)	−0.85034 (15)	0.0127 (3)
H12	0.391 (2)	0.7556 (18)	−0.9235 (17)	0.017 (4)*
C13	0.24500 (18)	0.95646 (15)	−0.88697 (14)	0.0115 (3)
C14	0.17579 (18)	1.01331 (15)	−0.77263 (14)	0.0129 (3)
H14	0.113 (2)	1.1128 (18)	−0.7893 (16)	0.013 (4)*
C15	0.19959 (18)	0.91909 (15)	−0.63026 (14)	0.0128 (3)
H15	0.159 (2)	0.9551 (16)	−0.5478 (16)	0.013 (4)*
C21	0.27741 (18)	1.09086 (15)	−1.30019 (14)	0.0126 (3)
H21	0.328 (2)	1.0541 (16)	−1.3816 (16)	0.012 (4)*
C22	0.30112 (18)	0.99866 (15)	−1.15749 (14)	0.0127 (3)
H22	0.376 (2)	0.8999 (17)	−1.1445 (15)	0.009 (3)*
C23	0.22327 (18)	1.05401 (15)	−1.04257 (14)	0.0111 (3)
C24	0.12511 (18)	1.20308 (15)	−1.07942 (14)	0.0125 (3)
H24	0.065 (2)	1.2487 (16)	−1.0073 (15)	0.009 (3)*
C25	0.10877 (18)	1.28843 (15)	−1.22582 (14)	0.0125 (3)
H25	0.0398 (19)	1.3925 (16)	−1.2530 (15)	0.009 (3)*
N2	0.18216 (15)	1.23362 (13)	−1.33515 (12)	0.0125 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0145 (6)	0.0081 (6)	0.0108 (6)	0.0004 (5)	−0.0028 (5)	−0.0050 (5)
C10	0.0102 (6)	0.0133 (7)	0.0115 (6)	−0.0020 (5)	−0.0050 (5)	−0.0046 (5)
O11	0.0178 (5)	0.0114 (5)	0.0116 (4)	−0.0010 (4)	−0.0038 (4)	−0.0028 (4)
O12	0.0130 (5)	0.0141 (5)	0.0089 (4)	−0.0001 (4)	−0.0019 (4)	−0.0040 (4)
C2	0.0136 (6)	0.0100 (6)	0.0121 (6)	0.0017 (5)	−0.0042 (5)	−0.0059 (5)
C20	0.0143 (6)	0.0084 (6)	0.0117 (6)	−0.0020 (5)	−0.0037 (5)	−0.0034 (5)
O21	0.0125 (5)	0.0159 (5)	0.0139 (5)	0.0005 (4)	−0.0037 (4)	−0.0059 (4)
O22	0.0145 (5)	0.0156 (5)	0.0096 (4)	0.0007 (4)	−0.0036 (4)	−0.0047 (4)
C3	0.0115 (6)	0.0099 (6)	0.0132 (6)	−0.0005 (5)	−0.0031 (5)	−0.0055 (5)
N1	0.0116 (6)	0.0128 (6)	0.0114 (5)	−0.0024 (4)	−0.0036 (5)	−0.0036 (4)
C11	0.0122 (6)	0.0126 (7)	0.0136 (6)	−0.0013 (5)	−0.0045 (5)	−0.0044 (5)
C12	0.0115 (6)	0.0150 (7)	0.0133 (6)	−0.0021 (5)	−0.0026 (5)	−0.0068 (5)
C13	0.0084 (6)	0.0140 (7)	0.0117 (6)	−0.0032 (5)	−0.0028 (5)	−0.0032 (5)
C14	0.0120 (6)	0.0118 (7)	0.0144 (7)	−0.0008 (5)	−0.0034 (5)	−0.0046 (5)
C15	0.0125 (6)	0.0141 (7)	0.0122 (6)	−0.0013 (5)	−0.0030 (5)	−0.0053 (5)
C21	0.0128 (6)	0.0146 (7)	0.0108 (6)	−0.0017 (5)	−0.0032 (5)	−0.0048 (5)
C22	0.0121 (6)	0.0120 (7)	0.0132 (6)	−0.0012 (5)	−0.0028 (5)	−0.0042 (5)
C23	0.0091 (6)	0.0136 (7)	0.0107 (6)	−0.0039 (5)	−0.0021 (5)	−0.0036 (5)
C24	0.0115 (6)	0.0151 (7)	0.0121 (6)	−0.0018 (5)	−0.0024 (5)	−0.0063 (5)
C25	0.0108 (6)	0.0119 (7)	0.0141 (6)	−0.0010 (5)	−0.0029 (5)	−0.0043 (5)
N2	0.0113 (5)	0.0139 (6)	0.0123 (5)	−0.0023 (4)	−0.0028 (4)	−0.0044 (4)

Geometric parameters (Å, º)

C1—C3^i	1.3943 (18)	C12—C13	1.3999 (18)
C1—C2	1.4038 (19)	C12—H12	0.984 (15)
C1—C10	1.5109 (17)	C13—C14	1.3984 (18)
C10—O11	1.2170 (16)	C13—C23	1.4966 (18)
C10—O12	1.3193 (15)	C14—C15	1.3860 (18)
O12—H2	0.99 (2)	C14—H14	0.931 (15)
C2—C3	1.3934 (18)	C15—H15	0.977 (14)
C2—C20	1.5192 (17)	C21—N2	1.3424 (17)
C20—O21	1.2350 (15)	C21—C22	1.3850 (18)
C20—O22	1.2828 (15)	C21—H21	0.973 (14)
O22—H1	1.40 (2)	C22—C23	1.3977 (17)
C3—C1^i	1.3943 (18)	C22—H22	0.960 (14)
C3—H3	0.957 (15)	C23—C24	1.3981 (18)
N1—C15	1.3372 (16)	C24—C25	1.3912 (18)
N1—C11	1.3435 (16)	C24—H24	0.954 (14)
N1—H1	1.14 (2)	C25—N2	1.3425 (16)
C11—C12	1.3831 (18)	C25—H25	0.977 (14)
C11—H11	0.962 (14)
C3^i—C1—C2	119.96 (12)	C14—C13—C12	117.36 (11)
C3^i—C1—C10	120.36 (12)	C14—C13—C23	121.35 (11)
C2—C1—C10	119.47 (11)	C12—C13—C23	121.29 (11)
O11—C10—O12	125.13 (12)	C15—C14—C13	119.40 (12)
O11—C10—C1	120.63 (11)	C15—C14—H14	118.9 (9)
O12—C10—C1	114.24 (11)	C13—C14—H14	121.7 (9)
C10—O12—H2	108.7 (12)	N1—C15—C14	121.85 (12)
C3—C2—C1	119.61 (11)	N1—C15—H15	115.7 (8)
C3—C2—C20	119.81 (12)	C14—C15—H15	122.4 (8)
C1—C2—C20	120.55 (11)	N2—C21—C22	123.01 (12)
O21—C20—O22	126.45 (11)	N2—C21—H21	115.9 (8)
O21—C20—C2	119.90 (11)	C22—C21—H21	121.1 (8)
O22—C20—C2	113.64 (11)	C21—C22—C23	119.65 (12)
C20—O22—H1	120.1 (8)	C21—C22—H22	116.8 (8)
C2—C3—C1^i	120.43 (12)	C23—C22—H22	123.5 (8)
C2—C3—H3	118.9 (8)	C22—C23—C24	117.23 (11)
C1^i—C3—H3	120.7 (8)	C22—C23—C13	120.85 (12)
C15—N1—C11	120.20 (11)	C24—C23—C13	121.91 (11)
C15—N1—H1	119.9 (10)	C25—C24—C23	119.47 (12)
C11—N1—H1	119.8 (10)	C25—C24—H24	117.9 (8)
N1—C11—C12	120.70 (12)	C23—C24—H24	122.6 (8)
N1—C11—H11	118.4 (8)	N2—C25—C24	122.88 (12)
C12—C11—H11	120.9 (8)	N2—C25—H25	116.8 (8)
C11—C12—C13	120.47 (12)	C24—C25—H25	120.3 (8)
C11—C12—H12	116.4 (9)	C21—N2—C25	117.75 (11)
C13—C12—H12	123.1 (9)

Symmetry code: (i) −x+1, −y+1, −z.