Diethyl 4-(4,5-dihydro-furan-2-yl)-3,5-di-methyl-1-phenyl-1,4-dihydro-pyrazine-2,6-dicarboxyl-ate.

In the title compound, C(22)H(26)N(2)O(5), the central 1,4-dihydro-pyrazine ring adopts a boat conformation, while the benzene ring and the two disordered components of the furan ring are inclined at angles of 77.9 (5) and 61.9 (7)°. Three of the C atoms of the furan ring are disordered over two positions with occupancies of 0.655 (18) and 0.345 (18). In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains propagating in [010].

Related literature

For the biological properties of 1,4-dihydro­pyrazines, see: Goto et al. (1968 ▶); Teranishi & Goto (1990 ▶). For their biomedical applications, see: Brook et al. (1992 ▶); Sit et al. (2002 ▶). For the synthesis of 1,4-dihydro­pyrazines, see: Wolfbeis (1977 ▶); Chorvat & Rorig (1988 ▶); Rodrigues et al. (2004 ▶).

Experimental

Crystal data

C22H26N2O5

M = 398.45

Triclinic,

a = 10.069 (2) Å

b = 10.242 (2) Å

c = 12.519 (3) Å

α = 72.37 (3)°

β = 77.59 (3)°

γ = 63.76 (3)°

V = 1098.8 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.50 × 0.40 × 0.25 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.958, T max = 0.979

7345 measured reflections

3768 independent reflections

1555 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.182

S = 0.84

3768 reflections

291 parameters

52 restraints

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.13 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2000 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2000 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013749/hb2937sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013749/hb2937Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H26N2O5	Z = 2
Mr = 398.45	F(000) = 424
Triclinic, P1	Dx = 1.204 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.069 (2) Å	Cell parameters from 7345 reflections
b = 10.242 (2) Å	θ = 2.3–25.0°
c = 12.519 (3) Å	µ = 0.09 mm−1
α = 72.37 (3)°	T = 293 K
β = 77.59 (3)°	Block, colourless
γ = 63.76 (3)°	0.50 × 0.40 × 0.25 mm
V = 1098.8 (4) Å3

Rigaku R-AXIS RAPID IP diffractometer	3768 independent reflections
Radiation source: fine-focus sealed tube	1555 reflections with I > 2σ(I)
graphite	Rint = 0.045
Detector resolution: 10.00 pixels mm-1	θmax = 25.0°, θmin = 2.3°
ω scans	h = −11→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→12
Tmin = 0.958, Tmax = 0.979	l = −14→13
7345 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059	H-atom parameters constrained
wR(F2) = 0.182	w = 1/[σ2(Fo2) + (0.102P)2] where P = (Fo2 + 2Fc2)/3
S = 0.84	(Δ/σ)max = 0.005
3768 reflections	Δρmax = 0.17 e Å−3
291 parameters	Δρmin = −0.13 e Å−3
52 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (5)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.6304 (3)	0.7169 (3)	0.1028 (2)	0.1226 (10)
O2	0.5222 (2)	0.5632 (3)	0.19260 (19)	0.0867 (7)
O3	0.1854 (3)	0.7014 (4)	0.5774 (2)	0.1395 (12)
O4	0.2987 (3)	0.5488 (3)	0.46179 (19)	0.1043 (9)
N1	0.2832 (3)	0.7643 (3)	0.2761 (2)	0.0696 (7)
N2	0.2680 (3)	1.0189 (3)	0.2870 (4)	0.1035 (11)
C1	0.4963 (4)	1.0117 (4)	0.1529 (3)	0.1177 (15)
H1A	0.4623	1.1095	0.1661	0.177*
H1B	0.5047	1.0198	0.0735	0.177*
H1C	0.5917	0.9491	0.1810	0.177*
C2	0.3879 (4)	0.9443 (4)	0.2120 (3)	0.0866 (11)
C3	0.4005 (3)	0.8073 (4)	0.2125 (3)	0.0699 (9)
C4	0.5280 (4)	0.6958 (4)	0.1640 (3)	0.0765 (9)
C5	0.1917 (4)	0.9956 (5)	0.4888 (4)	0.1324 (17)
H5A	0.1863	1.0960	0.4653	0.199*
H5B	0.2671	0.9352	0.5399	0.199*
H5C	0.0974	0.9967	0.5258	0.199*
C6	0.2298 (4)	0.9315 (5)	0.3880 (4)	0.0951 (12)
C7	0.2464 (3)	0.7984 (4)	0.3838 (3)	0.0760 (9)
C8	0.2383 (4)	0.6822 (5)	0.4836 (4)	0.0944 (11)
C9	0.6449 (4)	0.4402 (4)	0.1523 (3)	0.1075 (13)
H9A	0.6539	0.4641	0.0707	0.129*
H9B	0.7370	0.4254	0.1762	0.129*
C10	0.6198 (5)	0.3060 (5)	0.1958 (4)	0.1389 (18)
H10A	0.7012	0.2253	0.1686	0.208*
H10B	0.5290	0.3207	0.1714	0.208*
H10C	0.6124	0.2818	0.2766	0.208*
C11	0.3014 (6)	0.4218 (5)	0.5561 (4)	0.1469 (19)
H11A	0.3477	0.4207	0.6169	0.176*
H11B	0.2005	0.4318	0.5837	0.176*
C12	0.3823 (5)	0.2857 (6)	0.5208 (4)	0.1332 (16)
H12A	0.3808	0.2031	0.5824	0.200*
H12B	0.4833	0.2739	0.4966	0.200*
H12C	0.3375	0.2880	0.4595	0.200*
C13	0.1673 (3)	0.7858 (3)	0.2185 (3)	0.0658 (8)
C14	0.1859 (3)	0.7952 (4)	0.1046 (3)	0.0800 (10)
H14	0.2763	0.7905	0.0642	0.096*
C15	0.0733 (4)	0.8114 (4)	0.0497 (3)	0.1003 (12)
H15	0.0873	0.8206	−0.0276	0.120*
C16	−0.0604 (4)	0.8142 (4)	0.1082 (4)	0.1045 (12)
H16	−0.1357	0.8220	0.0716	0.125*
C17	−0.0797 (4)	0.8053 (4)	0.2212 (4)	0.0980 (12)
H17	−0.1702	0.8096	0.2612	0.118*
C18	0.0310 (3)	0.7903 (4)	0.2771 (3)	0.0848 (10)
H18	0.0155	0.7831	0.3542	0.102*
O5	0.2634 (3)	1.2572 (3)	0.2789 (2)	0.1113 (9)
C22	0.0984 (5)	1.2576 (5)	0.1768 (4)	0.1378 (18)
H22	0.0796	1.2188	0.1262	0.165*
C19A	0.1706 (10)	1.1824 (7)	0.2786 (9)	0.098 (3)	0.655 (18)
C20A	0.1744 (15)	1.4006 (12)	0.2440 (12)	0.133 (4)	0.655 (18)
H20A	0.2337	1.4551	0.1997	0.160*	0.655 (18)
H20B	0.1250	1.4425	0.3089	0.160*	0.655 (18)
C21A	0.0607 (17)	1.4213 (11)	0.1753 (14)	0.152 (5)	0.655 (18)
H21A	0.0713	1.4796	0.0994	0.182*	0.655 (18)
H21B	−0.0392	1.4690	0.2094	0.182*	0.655 (18)
C19B	0.2390 (19)	1.1784 (12)	0.2077 (18)	0.107 (6)	0.345 (18)
C20B	0.206 (4)	1.427 (3)	0.209 (3)	0.208 (17)	0.345 (18)
H20C	0.1396	1.4977	0.2540	0.250*	0.345 (18)
H20D	0.2851	1.4567	0.1676	0.250*	0.345 (18)
C21B	0.127 (3)	1.400 (2)	0.138 (2)	0.163 (12)	0.345 (18)
H21C	0.1837	1.3997	0.0645	0.196*	0.345 (18)
H21D	0.0321	1.4850	0.1274	0.196*	0.345 (18)

	U11	U22	U33	U12	U13	U23
O1	0.0867 (18)	0.118 (2)	0.146 (2)	−0.0465 (16)	0.0294 (17)	−0.0275 (18)
O2	0.0683 (14)	0.0740 (16)	0.1007 (17)	−0.0191 (12)	0.0113 (12)	−0.0256 (13)
O3	0.131 (2)	0.176 (3)	0.099 (2)	−0.048 (2)	0.0251 (18)	−0.063 (2)
O4	0.119 (2)	0.097 (2)	0.0760 (16)	−0.0355 (16)	0.0076 (14)	−0.0158 (15)
N1	0.0622 (16)	0.0669 (16)	0.0786 (18)	−0.0212 (12)	−0.0053 (14)	−0.0247 (14)
N2	0.081 (2)	0.063 (2)	0.171 (4)	−0.0093 (17)	−0.037 (2)	−0.048 (2)
C1	0.130 (3)	0.105 (3)	0.134 (3)	−0.076 (3)	−0.047 (3)	0.019 (3)
C2	0.091 (3)	0.064 (2)	0.108 (3)	−0.034 (2)	−0.045 (2)	0.005 (2)
C3	0.0558 (19)	0.069 (2)	0.075 (2)	−0.0206 (16)	−0.0101 (16)	−0.0075 (17)
C4	0.064 (2)	0.082 (3)	0.078 (2)	−0.0333 (19)	−0.0047 (18)	−0.008 (2)
C5	0.106 (3)	0.143 (4)	0.177 (4)	−0.029 (3)	−0.001 (3)	−0.118 (4)
C6	0.068 (2)	0.087 (3)	0.127 (4)	−0.017 (2)	−0.011 (2)	−0.044 (3)
C7	0.059 (2)	0.078 (2)	0.092 (3)	−0.0144 (17)	−0.0012 (17)	−0.047 (2)
C8	0.082 (3)	0.100 (3)	0.092 (3)	−0.020 (2)	−0.003 (2)	−0.040 (3)
C9	0.086 (3)	0.092 (3)	0.119 (3)	−0.018 (2)	0.018 (2)	−0.038 (2)
C10	0.133 (4)	0.095 (3)	0.172 (4)	−0.045 (3)	0.042 (3)	−0.051 (3)
C11	0.189 (5)	0.121 (4)	0.089 (3)	−0.057 (4)	0.021 (3)	0.000 (3)
C12	0.153 (4)	0.125 (4)	0.113 (4)	−0.059 (3)	−0.020 (3)	−0.009 (3)
C13	0.060 (2)	0.0530 (18)	0.083 (2)	−0.0165 (14)	−0.0107 (17)	−0.0202 (16)
C14	0.063 (2)	0.088 (2)	0.081 (3)	−0.0254 (17)	−0.0066 (18)	−0.0182 (19)
C15	0.083 (3)	0.124 (3)	0.086 (3)	−0.034 (2)	−0.022 (2)	−0.018 (2)
C16	0.073 (3)	0.118 (3)	0.120 (3)	−0.032 (2)	−0.023 (2)	−0.024 (3)
C17	0.062 (2)	0.111 (3)	0.115 (3)	−0.036 (2)	−0.001 (2)	−0.023 (3)
C18	0.060 (2)	0.101 (3)	0.090 (2)	−0.0280 (18)	−0.0035 (19)	−0.029 (2)
O5	0.1092 (18)	0.0695 (18)	0.166 (3)	−0.0273 (15)	−0.0492 (17)	−0.0316 (17)
C22	0.164 (5)	0.087 (3)	0.166 (4)	−0.034 (3)	−0.097 (4)	−0.006 (3)
C19A	0.088 (5)	0.053 (4)	0.160 (8)	−0.010 (3)	−0.044 (5)	−0.042 (4)
C20A	0.155 (9)	0.044 (5)	0.207 (10)	−0.045 (6)	−0.056 (8)	−0.004 (7)
C21A	0.141 (9)	0.093 (7)	0.218 (12)	−0.029 (6)	−0.094 (9)	−0.008 (7)
C19B	0.082 (10)	0.069 (8)	0.178 (15)	−0.004 (6)	−0.049 (9)	−0.054 (9)
C20B	0.152 (17)	0.117 (19)	0.32 (3)	−0.097 (14)	−0.059 (16)	0.092 (17)
C21B	0.19 (3)	0.073 (12)	0.184 (18)	−0.042 (14)	0.037 (17)	−0.033 (11)

O1—C4	1.207 (3)	C12—H12A	0.9600
O2—C4	1.320 (4)	C12—H12B	0.9600
O2—C9	1.452 (4)	C12—H12C	0.9600
O3—C8	1.216 (4)	C13—C14	1.376 (4)
O4—C8	1.316 (4)	C13—C18	1.398 (4)
O4—C11	1.462 (4)	C14—C15	1.373 (4)
N1—C13	1.404 (4)	C14—H14	0.9300
N1—C7	1.426 (4)	C15—C16	1.380 (5)
N1—C3	1.437 (4)	C15—H15	0.9300
N2—C6	1.399 (5)	C16—C17	1.367 (5)
N2—C2	1.433 (4)	C16—H16	0.9300
N2—C19A	1.504 (7)	C17—C18	1.368 (5)
N2—C19B	1.568 (15)	C17—H17	0.9300
C1—C2	1.492 (5)	C18—H18	0.9300
C1—H1A	0.9600	O5—C20A	1.329 (12)
C1—H1B	0.9600	O5—C19A	1.448 (8)
C1—H1C	0.9600	O5—C19B	1.488 (13)
C2—C3	1.350 (4)	O5—C20B	1.59 (2)
C3—C4	1.453 (4)	C22—C19B	1.357 (12)
C5—C6	1.498 (5)	C22—C19A	1.433 (8)
C5—H5A	0.9600	C22—C21B	1.530 (17)
C5—H5B	0.9600	C22—C21A	1.541 (10)
C5—H5C	0.9600	C22—H22	0.9300
C6—C7	1.314 (5)	C20A—C21A	1.480 (11)
C7—C8	1.458 (5)	C20A—H20A	0.9700
C9—C10	1.430 (5)	C20A—H20B	0.9700
C9—H9A	0.9700	C21A—H21A	0.9700
C9—H9B	0.9700	C21A—H21B	0.9700
C10—H10A	0.9600	C20B—C21B	1.460 (19)
C10—H10B	0.9600	C20B—H20C	0.9700
C10—H10C	0.9600	C20B—H20D	0.9700
C11—C12	1.420 (5)	C21B—H21C	0.9700
C11—H11A	0.9700	C21B—H21D	0.9700
C11—H11B	0.9700
C4—O2—C9	118.7 (3)	C14—C13—C18	118.0 (3)
C8—O4—C11	117.1 (3)	C14—C13—N1	121.6 (3)
C13—N1—C7	118.2 (2)	C18—C13—N1	120.4 (3)
C13—N1—C3	118.2 (3)	C15—C14—C13	121.1 (3)
C7—N1—C3	111.3 (3)	C15—C14—H14	119.5
C6—N2—C2	118.2 (3)	C13—C14—H14	119.5
C6—N2—C19A	110.6 (6)	C14—C15—C16	120.7 (4)
C2—N2—C19A	131.2 (6)	C14—C15—H15	119.7
C6—N2—C19B	148.5 (9)	C16—C15—H15	119.7
C2—N2—C19B	93.3 (8)	C17—C16—C15	118.4 (4)
C19A—N2—C19B	37.9 (5)	C17—C16—H16	120.8
C2—C1—H1A	109.5	C15—C16—H16	120.8
C2—C1—H1B	109.5	C16—C17—C18	121.6 (3)
H1A—C1—H1B	109.5	C16—C17—H17	119.2
C2—C1—H1C	109.5	C18—C17—H17	119.2
H1A—C1—H1C	109.5	C17—C18—C13	120.2 (3)
H1B—C1—H1C	109.5	C17—C18—H18	119.9
C3—C2—N2	114.5 (3)	C13—C18—H18	119.9
C3—C2—C1	125.7 (4)	C20A—O5—C19A	102.0 (6)
N2—C2—C1	119.4 (4)	C20A—O5—C19B	104.9 (6)
C2—C3—N1	116.4 (3)	C19A—O5—C19B	39.8 (6)
C2—C3—C4	125.7 (3)	C20A—O5—C20B	19.4 (15)
N1—C3—C4	117.7 (3)	C19A—O5—C20B	113.8 (11)
O1—C4—O2	121.2 (3)	C19B—O5—C20B	103.7 (12)
O1—C4—C3	125.7 (3)	C19B—C22—C19A	41.9 (7)
O2—C4—C3	113.1 (3)	C19B—C22—C21B	89.5 (15)
C6—C5—H5A	109.5	C19A—C22—C21B	102.7 (12)
C6—C5—H5B	109.5	C19B—C22—C21A	105.4 (7)
H5A—C5—H5B	109.5	C19A—C22—C21A	99.8 (6)
C6—C5—H5C	109.5	C21B—C22—C21A	27.0 (11)
H5A—C5—H5C	109.5	C19B—C22—H22	111.8
H5B—C5—H5C	109.5	C19A—C22—H22	130.1
C7—C6—N2	115.8 (4)	C21B—C22—H22	121.4
C7—C6—C5	128.6 (5)	C21A—C22—H22	130.1
N2—C6—C5	115.3 (4)	C22—C19A—O5	106.0 (6)
C6—C7—N1	117.6 (4)	C22—C19A—N2	114.1 (6)
C6—C7—C8	123.3 (4)	O5—C19A—N2	108.2 (5)
N1—C7—C8	118.9 (3)	O5—C20A—C21A	112.4 (8)
O3—C8—O4	122.4 (4)	O5—C20A—H20A	109.1
O3—C8—C7	125.8 (4)	C21A—C20A—H20A	109.1
O4—C8—C7	111.8 (3)	O5—C20A—H20B	109.1
C10—C9—O2	110.0 (3)	C21A—C20A—H20B	109.1
C10—C9—H9A	109.7	H20A—C20A—H20B	107.9
O2—C9—H9A	109.7	C20A—C21A—C22	101.2 (7)
C10—C9—H9B	109.7	C20A—C21A—H21A	111.5
O2—C9—H9B	109.7	C22—C21A—H21A	111.5
H9A—C9—H9B	108.2	C20A—C21A—H21B	111.5
C9—C10—H10A	109.5	C22—C21A—H21B	111.5
C9—C10—H10B	109.5	H21A—C21A—H21B	109.4
H10A—C10—H10B	109.5	C22—C19B—O5	107.9 (10)
C9—C10—H10C	109.5	C22—C19B—N2	114.6 (12)
H10A—C10—H10C	109.5	O5—C19B—N2	103.0 (11)
H10B—C10—H10C	109.5	C21B—C20B—O5	92.0 (15)
C12—C11—O4	110.0 (4)	C21B—C20B—H20C	113.3
C12—C11—H11A	109.7	O5—C20B—H20C	113.3
O4—C11—H11A	109.7	C21B—C20B—H20D	113.3
C12—C11—H11B	109.7	O5—C20B—H20D	113.3
O4—C11—H11B	109.7	H20C—C20B—H20D	110.6
H11A—C11—H11B	108.2	C20B—C21B—C22	118.7 (18)
C11—C12—H12A	109.5	C20B—C21B—H21C	107.6
C11—C12—H12B	109.5	C22—C21B—H21C	107.6
H12A—C12—H12B	109.5	C20B—C21B—H21D	107.6
C11—C12—H12C	109.5	C22—C21B—H21D	107.6
H12A—C12—H12C	109.5	H21C—C21B—H21D	107.1
H12B—C12—H12C	109.5
C6—N2—C2—C3	33.1 (4)	C14—C13—C18—C17	−0.7 (5)
C19A—N2—C2—C3	−147.6 (4)	N1—C13—C18—C17	−177.4 (3)
C19B—N2—C2—C3	−147.0 (5)	C19B—C22—C19A—O5	61.0 (10)
C6—N2—C2—C1	−139.4 (3)	C21B—C22—C19A—O5	−13.7 (15)
C19A—N2—C2—C1	39.8 (6)	C21A—C22—C19A—O5	−41.1 (12)
C19B—N2—C2—C1	40.5 (5)	C19B—C22—C19A—N2	−58.0 (10)
N2—C2—C3—N1	7.5 (4)	C21B—C22—C19A—N2	−132.6 (11)
C1—C2—C3—N1	179.5 (3)	C21A—C22—C19A—N2	−160.1 (7)
N2—C2—C3—C4	−166.2 (3)	C20A—O5—C19A—C22	42.6 (11)
C1—C2—C3—C4	5.8 (5)	C19B—O5—C19A—C22	−56.4 (9)
C13—N1—C3—C2	96.3 (3)	C20B—O5—C19A—C22	26.4 (16)
C7—N1—C3—C2	−45.5 (4)	C20A—O5—C19A—N2	165.4 (7)
C13—N1—C3—C4	−89.5 (3)	C19B—O5—C19A—N2	66.4 (9)
C7—N1—C3—C4	128.7 (3)	C20B—O5—C19A—N2	149.2 (13)
C9—O2—C4—O1	2.2 (5)	C6—N2—C19A—C22	−126.8 (7)
C9—O2—C4—C3	−178.4 (3)	C2—N2—C19A—C22	53.9 (9)
C2—C3—C4—O1	−11.4 (5)	C19B—N2—C19A—C22	52.9 (9)
N1—C3—C4—O1	175.0 (3)	C6—N2—C19A—O5	115.4 (6)
C2—C3—C4—O2	169.1 (3)	C2—N2—C19A—O5	−63.9 (8)
N1—C3—C4—O2	−4.5 (4)	C19B—N2—C19A—O5	−64.9 (10)
C2—N2—C6—C7	−33.5 (5)	C19A—O5—C20A—C21A	−25.3 (13)
C19A—N2—C6—C7	147.1 (4)	C19B—O5—C20A—C21A	15.6 (16)
C19B—N2—C6—C7	146.8 (9)	C20B—O5—C20A—C21A	104 (4)
C2—N2—C6—C5	140.0 (3)	O5—C20A—C21A—C22	0.7 (14)
C19A—N2—C6—C5	−39.4 (5)	C19B—C22—C21A—C20A	−18.3 (17)
C19B—N2—C6—C5	−39.7 (10)	C19A—C22—C21A—C20A	24.3 (13)
N2—C6—C7—N1	−7.5 (4)	C21B—C22—C21A—C20A	−74 (3)
C5—C6—C7—N1	−180.0 (3)	C19A—C22—C19B—O5	−59.3 (12)
N2—C6—C7—C8	168.5 (3)	C21B—C22—C19B—O5	50.5 (17)
C5—C6—C7—C8	−3.9 (6)	C21A—C22—C19B—O5	28.3 (19)
C13—N1—C7—C6	−95.6 (4)	C19A—C22—C19B—N2	54.7 (13)
C3—N1—C7—C6	46.2 (4)	C21B—C22—C19B—N2	164.5 (13)
C13—N1—C7—C8	88.2 (3)	C21A—C22—C19B—N2	142.4 (9)
C3—N1—C7—C8	−130.0 (3)	C20A—O5—C19B—C22	−28.3 (19)
C11—O4—C8—O3	−0.6 (6)	C19A—O5—C19B—C22	62.6 (12)
C11—O4—C8—C7	178.3 (3)	C20B—O5—C19B—C22	−48 (2)
C6—C7—C8—O3	16.8 (6)	C20A—O5—C19B—N2	−149.9 (8)
N1—C7—C8—O3	−167.2 (3)	C19A—O5—C19B—N2	−58.9 (12)
C6—C7—C8—O4	−162.0 (3)	C20B—O5—C19B—N2	−169.8 (13)
N1—C7—C8—O4	14.0 (4)	C6—N2—C19B—C22	−57.1 (17)
C4—O2—C9—C10	177.9 (3)	C2—N2—C19B—C22	123.1 (12)
C8—O4—C11—C12	−174.4 (4)	C19A—N2—C19B—C22	−57.7 (13)
C7—N1—C13—C14	162.1 (3)	C6—N2—C19B—O5	59.8 (14)
C3—N1—C13—C14	23.0 (4)	C2—N2—C19B—O5	−120.0 (10)
C7—N1—C13—C18	−21.2 (4)	C19A—N2—C19B—O5	59.2 (11)
C3—N1—C13—C18	−160.4 (3)	C20A—O5—C20B—C21B	−81 (4)
C18—C13—C14—C15	1.2 (5)	C19A—O5—C20B—C21B	−25 (2)
N1—C13—C14—C15	177.9 (3)	C19B—O5—C20B—C21B	16 (2)
C13—C14—C15—C16	−1.9 (5)	O5—C20B—C21B—C22	16 (3)
C14—C15—C16—C17	2.1 (6)	C19B—C22—C21B—C20B	−43 (3)
C15—C16—C17—C18	−1.6 (6)	C19A—C22—C21B—C20B	−3(3)
C16—C17—C18—C13	0.9 (5)	C21A—C22—C21B—C20B	84 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···O5i	0.96	2.67	3.618 (5)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12C⋯O5i	0.96	2.67	3.618 (5)	169

Symmetry code: (i) .