A triclinic polymorph of (E)-2-(2-nitro-ethen-yl)furan.

The title compound, C(6)H(5)NO(3), crystallizes in the triclinic system with six independent mol-ecules in the asymmetric unit. In a previous study, the structure of the title compound was determined in the monoclinic P2(1)/n space group at 100 K [Valerga et al. (2009 ▶). Acta Cryst. E65, o1979]. All six independent mol-ecules display an E configuration about the C=C double bond, with the dihedral angles between the planes of the furan rings and the nitro-alkenyl groups ranging from 0.61 (7) to 5.03 (7)°. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen-bonding inter-actions.

Related literature

For the use of nitro­alkenes in organic synthesis, see: Ranu et al. (2005 ▶); Ballini & Bosica (2005 ▶); Ono (2005 ▶). For the structure of the monoclinic polymorph, see: Valerga et al. (2009 ▶).

Experimental

Crystal data

C6H5NO3

M = 139.11

Triclinic,

a = 9.8407 (14) Å

b = 13.4270 (19) Å

c = 15.300 (2) Å

α = 91.105 (1)°

β = 108.603 (2)°

γ = 91.172 (1)°

V = 1914.8 (5) Å3

Z = 12

Mo Kα radiation

μ = 0.12 mm−1

T = 298 K

0.12 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.976, T max = 0.988

13307 measured reflections

8182 independent reflections

4235 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.149

S = 0.92

8182 reflections

541 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002492X/rz2466sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002492X/rz2466Isup2.hkl

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

C6H5NO3	Z = 12
Mr = 139.11	F(000) = 864
Triclinic, P1	Dx = 1.448 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8407 (14) Å	Cell parameters from 2345 reflections
b = 13.4270 (19) Å	θ = 1.2–25.9°
c = 15.300 (2) Å	µ = 0.12 mm−1
α = 91.105 (1)°	T = 298 K
β = 108.603 (2)°	Block, colourless
γ = 91.172 (1)°	0.12 × 0.10 × 0.10 mm
V = 1914.8 (5) Å3

Bruker SMART CCD area-detector diffractometer	8182 independent reflections
Radiation source: fine-focus sealed tube	4235 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −12→12
Tmin = 0.976, Tmax = 0.988	k = −16→17
13307 measured reflections	l = −14→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.0705P)2] where P = (Fo2 + 2Fc2)/3
8182 reflections	(Δ/σ)max = 0.002
541 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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
C1	0.9416 (2)	0.92135 (16)	0.24460 (16)	0.0650 (6)
H1	0.9831	0.9532	0.2056	0.078*
C2	1.0123 (2)	0.86624 (16)	0.31429 (16)	0.0644 (6)
H2	1.1096	0.8528	0.3329	0.077*
C3	0.9112 (2)	0.83226 (15)	0.35424 (15)	0.0599 (6)
H3	0.9288	0.7912	0.4047	0.072*
C4	0.7841 (2)	0.86944 (14)	0.30671 (14)	0.0479 (5)
C5	0.6460 (2)	0.85930 (14)	0.31761 (14)	0.0517 (5)
H5	0.6387	0.8211	0.3661	0.062*
C6	0.5279 (2)	0.89934 (15)	0.26493 (14)	0.0539 (5)
H6	0.5308	0.9382	0.2159	0.065*
C7	0.7237 (2)	0.63452 (14)	0.18843 (14)	0.0491 (5)
C8	0.8029 (2)	0.67212 (15)	0.13981 (16)	0.0638 (6)
H8	0.7714	0.7146	0.0905	0.077*
C9	0.9416 (2)	0.63636 (16)	0.17613 (17)	0.0669 (7)
H9	1.0196	0.6501	0.1560	0.080*
C10	0.9392 (2)	0.57880 (16)	0.24518 (17)	0.0657 (6)
H10	1.0178	0.5452	0.2819	0.079*
C11	0.5770 (2)	0.64540 (14)	0.18134 (14)	0.0515 (5)
H11	0.5239	0.6880	0.1368	0.062*
C12	0.5094 (2)	0.60051 (15)	0.23223 (15)	0.0567 (6)
H12	0.5587	0.5573	0.2776	0.068*
C13	0.8059 (2)	0.37791 (14)	0.10512 (14)	0.0484 (5)
C14	0.6775 (2)	0.40843 (14)	0.05235 (15)	0.0570 (6)
H14	0.6596	0.4424	−0.0024	0.068*
C15	0.5752 (2)	0.38043 (15)	0.09389 (16)	0.0599 (6)
H15	0.4772	0.3915	0.0726	0.072*
C16	0.6481 (2)	0.33457 (16)	0.17040 (16)	0.0643 (6)
H16	0.6070	0.3081	0.2121	0.077*
C17	0.9454 (2)	0.38754 (14)	0.09616 (14)	0.0498 (5)
H17	0.9525	0.4201	0.0446	0.060*
C18	1.0657 (2)	0.35470 (14)	0.15413 (14)	0.0525 (5)
H18	1.0631	0.3202	0.2057	0.063*
C19	0.8813 (2)	0.13701 (14)	0.01911 (15)	0.0495 (5)
C20	0.9605 (2)	0.15719 (15)	−0.03563 (16)	0.0607 (6)
H20	0.9267	0.1808	−0.0953	0.073*
C21	1.1038 (2)	0.13626 (15)	0.01342 (18)	0.0660 (6)
H21	1.1826	0.1428	−0.0073	0.079*
C22	1.1038 (2)	0.10540 (16)	0.09513 (18)	0.0697 (7)
H22	1.1852	0.0868	0.1418	0.084*
C23	0.7319 (2)	0.14092 (14)	0.00502 (15)	0.0512 (5)
H23	0.6750	0.1662	−0.0504	0.061*
C24	0.6664 (2)	0.11183 (15)	0.06361 (15)	0.0565 (6)
H24	0.7199	0.0866	0.1200	0.068*
C25	0.7166 (2)	0.11542 (14)	0.39786 (15)	0.0505 (5)
C26	0.6371 (2)	0.08594 (15)	0.45004 (16)	0.0640 (6)
H26	0.6703	0.0533	0.5056	0.077*
C27	0.4949 (2)	0.11306 (16)	0.40575 (18)	0.0675 (7)
H27	0.4161	0.1022	0.4258	0.081*
C28	0.4967 (2)	0.15721 (17)	0.32982 (19)	0.0766 (7)
H28	0.4164	0.1829	0.2868	0.092*
C29	0.8654 (2)	0.10866 (14)	0.40970 (14)	0.0512 (5)
H29	0.9203	0.0741	0.4604	0.061*
C30	0.9330 (2)	0.14664 (15)	0.35584 (15)	0.0564 (6)
H30	0.8818	0.1819	0.3046	0.068*
C31	0.6315 (2)	0.36980 (14)	0.48376 (15)	0.0505 (5)
C32	0.7617 (2)	0.34777 (16)	0.53904 (15)	0.0635 (6)
H32	0.7822	0.3193	0.5966	0.076*
C33	0.8624 (2)	0.37469 (15)	0.49599 (17)	0.0628 (6)
H33	0.9613	0.3678	0.5186	0.075*
C34	0.7873 (3)	0.41190 (17)	0.41671 (17)	0.0739 (7)
H34	0.8270	0.4361	0.3734	0.089*
C35	0.4923 (2)	0.35871 (14)	0.49243 (14)	0.0522 (5)
H35	0.4868	0.3295	0.5459	0.063*
C36	0.3707 (2)	0.38543 (15)	0.43283 (15)	0.0565 (6)
H36	0.3716	0.4150	0.3785	0.068*
N1	0.39430 (19)	0.88338 (14)	0.28277 (13)	0.0603 (5)
N2	0.3605 (2)	0.61778 (13)	0.21816 (13)	0.0608 (5)
N3	1.19984 (19)	0.37178 (13)	0.13825 (14)	0.0597 (5)
N4	0.51390 (19)	0.11858 (12)	0.04148 (14)	0.0589 (5)
N5	1.08370 (18)	0.13472 (13)	0.37455 (13)	0.0574 (5)
N6	0.23663 (19)	0.36992 (13)	0.44974 (14)	0.0600 (5)
O1	0.80031 (15)	0.92554 (10)	0.23725 (10)	0.0586 (4)
O2	0.38865 (17)	0.82959 (14)	0.34471 (12)	0.0853 (5)
O3	0.29023 (16)	0.92505 (12)	0.23200 (12)	0.0870 (5)
O4	0.80683 (15)	0.57538 (10)	0.25532 (10)	0.0614 (4)
O5	0.30358 (18)	0.57248 (13)	0.26641 (12)	0.0847 (5)
O6	0.29579 (16)	0.67661 (12)	0.16014 (11)	0.0804 (5)
O7	0.79022 (15)	0.33117 (10)	0.17990 (9)	0.0588 (4)
O8	1.30633 (16)	0.33720 (12)	0.19333 (12)	0.0844 (5)
O9	1.20458 (17)	0.41996 (14)	0.07243 (12)	0.0877 (6)
O10	0.96849 (15)	0.10452 (10)	0.10184 (10)	0.0629 (4)
O11	0.44264 (16)	0.15312 (12)	−0.03166 (11)	0.0803 (5)
O12	0.46063 (17)	0.08859 (13)	0.09852 (12)	0.0849 (5)
O13	0.63096 (15)	0.16044 (11)	0.32253 (11)	0.0711 (5)
O14	1.15176 (16)	0.09038 (12)	0.44346 (11)	0.0782 (5)
O15	1.13827 (17)	0.17002 (12)	0.32070 (12)	0.0805 (5)
O16	0.64420 (16)	0.41055 (11)	0.40583 (10)	0.0709 (5)
O17	0.23464 (18)	0.33222 (13)	0.52140 (13)	0.0894 (6)
O18	0.12831 (16)	0.39605 (12)	0.39036 (11)	0.0817 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0618 (16)	0.0695 (15)	0.0780 (17)	−0.0058 (12)	0.0427 (14)	0.0025 (13)
C2	0.0469 (13)	0.0728 (15)	0.0772 (17)	0.0049 (11)	0.0246 (13)	0.0062 (13)
C3	0.0560 (14)	0.0666 (14)	0.0570 (14)	0.0048 (11)	0.0171 (12)	0.0129 (11)
C4	0.0490 (13)	0.0499 (12)	0.0475 (13)	−0.0027 (9)	0.0190 (10)	0.0047 (10)
C5	0.0531 (13)	0.0529 (12)	0.0511 (13)	−0.0015 (10)	0.0195 (11)	0.0040 (10)
C6	0.0502 (13)	0.0580 (13)	0.0565 (14)	−0.0032 (10)	0.0215 (11)	0.0050 (10)
C7	0.0463 (12)	0.0480 (12)	0.0522 (13)	0.0049 (9)	0.0142 (10)	0.0078 (10)
C8	0.0573 (14)	0.0591 (14)	0.0791 (17)	0.0037 (11)	0.0264 (13)	0.0173 (12)
C9	0.0541 (15)	0.0621 (15)	0.0925 (19)	0.0008 (11)	0.0344 (14)	0.0078 (13)
C10	0.0481 (14)	0.0652 (15)	0.0800 (18)	0.0130 (11)	0.0144 (12)	0.0033 (13)
C11	0.0502 (13)	0.0460 (12)	0.0575 (14)	0.0037 (9)	0.0158 (11)	0.0053 (10)
C12	0.0507 (13)	0.0602 (13)	0.0621 (15)	0.0135 (10)	0.0207 (12)	0.0092 (11)
C13	0.0480 (12)	0.0481 (12)	0.0525 (13)	−0.0016 (9)	0.0210 (10)	0.0071 (10)
C14	0.0487 (13)	0.0608 (13)	0.0608 (14)	0.0065 (10)	0.0156 (11)	0.0135 (11)
C15	0.0432 (12)	0.0628 (14)	0.0753 (16)	0.0035 (10)	0.0208 (12)	0.0050 (12)
C16	0.0562 (15)	0.0691 (15)	0.0791 (17)	−0.0022 (11)	0.0378 (13)	0.0097 (13)
C17	0.0507 (13)	0.0516 (12)	0.0514 (13)	−0.0012 (10)	0.0223 (10)	0.0042 (10)
C18	0.0462 (12)	0.0584 (13)	0.0573 (14)	−0.0003 (10)	0.0226 (11)	0.0071 (10)
C19	0.0449 (12)	0.0456 (12)	0.0581 (14)	0.0041 (9)	0.0161 (11)	0.0067 (10)
C20	0.0558 (14)	0.0641 (14)	0.0666 (15)	0.0086 (11)	0.0244 (12)	0.0153 (12)
C21	0.0523 (14)	0.0609 (14)	0.0933 (19)	0.0058 (11)	0.0343 (14)	0.0140 (13)
C22	0.0402 (13)	0.0669 (15)	0.097 (2)	0.0073 (10)	0.0131 (13)	0.0213 (14)
C23	0.0449 (12)	0.0487 (12)	0.0589 (14)	0.0041 (9)	0.0147 (11)	0.0060 (10)
C24	0.0408 (12)	0.0586 (13)	0.0652 (15)	0.0022 (10)	0.0100 (11)	0.0069 (11)
C25	0.0444 (12)	0.0465 (12)	0.0606 (14)	0.0040 (9)	0.0165 (11)	0.0053 (10)
C26	0.0591 (15)	0.0654 (15)	0.0714 (16)	0.0058 (11)	0.0258 (13)	0.0098 (12)
C27	0.0523 (14)	0.0587 (14)	0.099 (2)	0.0009 (11)	0.0341 (14)	0.0041 (13)
C28	0.0416 (13)	0.0735 (16)	0.110 (2)	0.0120 (11)	0.0151 (14)	0.0239 (15)
C29	0.0441 (12)	0.0502 (12)	0.0580 (14)	0.0041 (9)	0.0140 (10)	0.0055 (10)
C30	0.0418 (12)	0.0607 (13)	0.0644 (15)	0.0063 (10)	0.0130 (11)	0.0113 (11)
C31	0.0547 (14)	0.0463 (12)	0.0535 (14)	−0.0002 (10)	0.0212 (11)	0.0068 (10)
C32	0.0570 (14)	0.0734 (15)	0.0646 (15)	0.0101 (11)	0.0241 (13)	0.0195 (12)
C33	0.0493 (13)	0.0651 (14)	0.0773 (17)	0.0053 (11)	0.0241 (13)	0.0112 (12)
C34	0.0607 (16)	0.0906 (18)	0.0818 (19)	−0.0017 (13)	0.0385 (14)	0.0167 (14)
C35	0.0546 (13)	0.0515 (12)	0.0549 (14)	0.0029 (10)	0.0232 (11)	0.0059 (10)
C36	0.0501 (13)	0.0594 (13)	0.0638 (15)	−0.0009 (10)	0.0233 (12)	0.0082 (11)
N1	0.0445 (11)	0.0722 (13)	0.0635 (13)	−0.0022 (9)	0.0162 (10)	0.0023 (10)
N2	0.0531 (12)	0.0695 (13)	0.0664 (13)	0.0092 (10)	0.0277 (10)	0.0066 (10)
N3	0.0474 (11)	0.0686 (12)	0.0667 (13)	0.0013 (9)	0.0232 (10)	0.0070 (10)
N4	0.0449 (11)	0.0592 (12)	0.0732 (14)	0.0007 (9)	0.0194 (10)	0.0058 (10)
N5	0.0436 (11)	0.0605 (12)	0.0689 (14)	0.0040 (9)	0.0186 (10)	0.0046 (10)
N6	0.0503 (12)	0.0578 (12)	0.0761 (14)	0.0038 (9)	0.0257 (11)	0.0066 (10)
O1	0.0573 (9)	0.0610 (9)	0.0617 (10)	0.0035 (7)	0.0243 (8)	0.0130 (7)
O2	0.0609 (11)	0.1205 (14)	0.0839 (13)	0.0062 (10)	0.0338 (9)	0.0390 (11)
O3	0.0484 (10)	0.1061 (13)	0.1021 (13)	0.0130 (9)	0.0155 (9)	0.0318 (10)
O4	0.0534 (9)	0.0672 (10)	0.0656 (10)	0.0106 (7)	0.0203 (8)	0.0171 (8)
O5	0.0710 (11)	0.1055 (13)	0.0971 (13)	0.0118 (10)	0.0522 (10)	0.0297 (10)
O6	0.0586 (10)	0.1003 (13)	0.0887 (12)	0.0279 (9)	0.0290 (9)	0.0350 (10)
O7	0.0507 (9)	0.0679 (10)	0.0616 (10)	0.0032 (7)	0.0220 (7)	0.0174 (8)
O8	0.0466 (9)	0.1086 (13)	0.0965 (13)	0.0181 (9)	0.0180 (9)	0.0305 (10)
O9	0.0608 (11)	0.1255 (15)	0.0889 (13)	0.0044 (10)	0.0385 (10)	0.0417 (11)
O10	0.0447 (9)	0.0705 (10)	0.0728 (11)	0.0043 (7)	0.0161 (8)	0.0234 (8)
O11	0.0480 (9)	0.1092 (13)	0.0791 (12)	0.0135 (9)	0.0119 (9)	0.0261 (10)
O12	0.0587 (11)	0.1081 (14)	0.0985 (14)	−0.0004 (9)	0.0386 (10)	0.0290 (11)
O13	0.0428 (9)	0.0858 (11)	0.0836 (12)	0.0072 (8)	0.0167 (8)	0.0322 (9)
O14	0.0495 (9)	0.1025 (13)	0.0824 (12)	0.0191 (9)	0.0184 (9)	0.0287 (10)
O15	0.0602 (10)	0.1047 (13)	0.0902 (13)	0.0043 (9)	0.0414 (10)	0.0295 (10)
O16	0.0574 (10)	0.0928 (12)	0.0663 (11)	0.0032 (8)	0.0235 (8)	0.0250 (9)
O17	0.0698 (12)	0.1143 (14)	0.0977 (14)	0.0103 (10)	0.0431 (11)	0.0430 (11)
O18	0.0482 (10)	0.1026 (13)	0.0895 (13)	0.0134 (9)	0.0139 (9)	0.0155 (10)

C1—C2	1.321 (3)	C21—H21	0.9300
C1—O1	1.362 (2)	C22—O10	1.368 (3)
C1—H1	0.9300	C22—H22	0.9300
C2—C3	1.397 (3)	C23—C24	1.320 (3)
C2—H2	0.9300	C23—H23	0.9300
C3—C4	1.342 (3)	C24—N4	1.434 (2)
C3—H3	0.9300	C24—H24	0.9300
C4—O1	1.362 (2)	C25—C26	1.343 (3)
C4—C5	1.425 (3)	C25—O13	1.353 (2)
C5—C6	1.317 (3)	C25—C29	1.422 (3)
C5—H5	0.9300	C26—C27	1.405 (3)
C6—N1	1.438 (3)	C26—H26	0.9300
C6—H6	0.9300	C27—C28	1.319 (3)
C7—C8	1.336 (3)	C27—H27	0.9300
C7—O4	1.368 (2)	C28—O13	1.361 (3)
C7—C11	1.424 (3)	C28—H28	0.9300
C8—C9	1.398 (3)	C29—C30	1.317 (3)
C8—H8	0.9300	C29—H29	0.9300
C9—C10	1.327 (3)	C30—N5	1.431 (2)
C9—H9	0.9300	C30—H30	0.9300
C10—O4	1.360 (2)	C31—C32	1.334 (3)
C10—H10	0.9300	C31—O16	1.362 (2)
C11—C12	1.320 (3)	C31—C35	1.423 (3)
C11—H11	0.9300	C32—C33	1.399 (3)
C12—N2	1.436 (3)	C32—H32	0.9300
C12—H12	0.9300	C33—C34	1.317 (3)
C13—C14	1.341 (3)	C33—H33	0.9300
C13—O7	1.365 (2)	C34—O16	1.364 (3)
C13—C17	1.426 (3)	C34—H34	0.9300
C14—C15	1.401 (3)	C35—C36	1.314 (3)
C14—H14	0.9300	C35—H35	0.9300
C15—C16	1.332 (3)	C36—N6	1.435 (3)
C15—H15	0.9300	C36—H36	0.9300
C16—O7	1.361 (2)	N1—O2	1.217 (2)
C16—H16	0.9300	N1—O3	1.224 (2)
C17—C18	1.323 (3)	N2—O5	1.223 (2)
C17—H17	0.9300	N2—O6	1.226 (2)
C18—N3	1.431 (3)	N3—O9	1.220 (2)
C18—H18	0.9300	N3—O8	1.223 (2)
C19—C20	1.341 (3)	N4—O11	1.221 (2)
C19—O10	1.368 (2)	N4—O12	1.223 (2)
C19—C23	1.419 (3)	N5—O15	1.216 (2)
C20—C21	1.407 (3)	N5—O14	1.227 (2)
C20—H20	0.9300	N6—O17	1.222 (2)
C21—C22	1.325 (3)	N6—O18	1.222 (2)
C2—C1—O1	111.4 (2)	C24—C23—C19	125.8 (2)
C2—C1—H1	124.3	C24—C23—H23	117.1
O1—C1—H1	124.3	C19—C23—H23	117.1
C1—C2—C3	106.0 (2)	C23—C24—N4	120.9 (2)
C1—C2—H2	127.0	C23—C24—H24	119.5
C3—C2—H2	127.0	N4—C24—H24	119.5
C4—C3—C2	107.74 (19)	C26—C25—O13	108.90 (18)
C4—C3—H3	126.1	C26—C25—C29	132.1 (2)
C2—C3—H3	126.1	O13—C25—C29	119.0 (2)
C3—C4—O1	109.20 (18)	C25—C26—C27	107.9 (2)
C3—C4—C5	131.5 (2)	C25—C26—H26	126.0
O1—C4—C5	119.26 (19)	C27—C26—H26	126.0
C6—C5—C4	125.6 (2)	C28—C27—C26	105.5 (2)
C6—C5—H5	117.2	C28—C27—H27	127.2
C4—C5—H5	117.2	C26—C27—H27	127.2
C5—C6—N1	120.4 (2)	C27—C28—O13	111.4 (2)
C5—C6—H6	119.8	C27—C28—H28	124.3
N1—C6—H6	119.8	O13—C28—H28	124.3
C8—C7—O4	109.22 (18)	C30—C29—C25	126.3 (2)
C8—C7—C11	131.9 (2)	C30—C29—H29	116.9
O4—C7—C11	118.83 (19)	C25—C29—H29	116.9
C7—C8—C9	107.9 (2)	C29—C30—N5	121.3 (2)
C7—C8—H8	126.0	C29—C30—H30	119.3
C9—C8—H8	126.0	N5—C30—H30	119.3
C10—C9—C8	106.0 (2)	C32—C31—O16	108.79 (19)
C10—C9—H9	127.0	C32—C31—C35	132.6 (2)
C8—C9—H9	127.0	O16—C31—C35	118.58 (19)
C9—C10—O4	111.2 (2)	C31—C32—C33	108.6 (2)
C9—C10—H10	124.4	C31—C32—H32	125.7
O4—C10—H10	124.4	C33—C32—H32	125.7
C12—C11—C7	126.0 (2)	C34—C33—C32	105.3 (2)
C12—C11—H11	117.0	C34—C33—H33	127.4
C7—C11—H11	117.0	C32—C33—H33	127.4
C11—C12—N2	120.57 (19)	C33—C34—O16	111.7 (2)
C11—C12—H12	119.7	C33—C34—H34	124.1
N2—C12—H12	119.7	O16—C34—H34	124.1
C14—C13—O7	109.09 (18)	C36—C35—C31	126.8 (2)
C14—C13—C17	131.9 (2)	C36—C35—H35	116.6
O7—C13—C17	119.01 (18)	C31—C35—H35	116.6
C13—C14—C15	108.30 (19)	C35—C36—N6	121.4 (2)
C13—C14—H14	125.8	C35—C36—H36	119.3
C15—C14—H14	125.8	N6—C36—H36	119.3
C16—C15—C14	105.28 (19)	O2—N1—O3	123.55 (19)
C16—C15—H15	127.4	O2—N1—C6	120.06 (19)
C14—C15—H15	127.4	O3—N1—C6	116.38 (19)
C15—C16—O7	111.6 (2)	O5—N2—O6	122.62 (19)
C15—C16—H16	124.2	O5—N2—C12	117.32 (18)
O7—C16—H16	124.2	O6—N2—C12	120.07 (19)
C18—C17—C13	126.3 (2)	O9—N3—O8	122.83 (19)
C18—C17—H17	116.9	O9—N3—C18	119.96 (18)
C13—C17—H17	116.9	O8—N3—C18	117.21 (19)
C17—C18—N3	120.6 (2)	O11—N4—O12	122.61 (19)
C17—C18—H18	119.7	O11—N4—C24	120.2 (2)
N3—C18—H18	119.7	O12—N4—C24	117.14 (19)
C20—C19—O10	109.30 (18)	O15—N5—O14	123.11 (18)
C20—C19—C23	132.3 (2)	O15—N5—C30	117.66 (19)
O10—C19—C23	118.35 (19)	O14—N5—C30	119.2 (2)
C19—C20—C21	107.7 (2)	O17—N6—O18	122.96 (19)
C19—C20—H20	126.2	O17—N6—C36	119.78 (19)
C21—C20—H20	126.2	O18—N6—C36	117.3 (2)
C22—C21—C20	106.1 (2)	C1—O1—C4	105.67 (17)
C22—C21—H21	127.0	C10—O4—C7	105.69 (17)
C20—C21—H21	127.0	C16—O7—C13	105.73 (16)
C21—C22—O10	111.2 (2)	C22—O10—C19	105.77 (18)
C21—C22—H22	124.4	C25—O13—C28	106.26 (18)
O10—C22—H22	124.4	C31—O16—C34	105.61 (17)
O1—C1—C2—C3	0.3 (3)	C35—C31—C32—C33	−179.9 (2)
C1—C2—C3—C4	−0.4 (3)	C31—C32—C33—C34	0.1 (3)
C2—C3—C4—O1	0.4 (2)	C32—C33—C34—O16	−0.1 (3)
C2—C3—C4—C5	−179.7 (2)	C32—C31—C35—C36	178.6 (2)
C3—C4—C5—C6	−179.2 (2)	O16—C31—C35—C36	−1.2 (3)
O1—C4—C5—C6	0.7 (3)	C31—C35—C36—N6	179.89 (18)
C4—C5—C6—N1	179.79 (18)	C5—C6—N1—O2	−2.8 (3)
O4—C7—C8—C9	0.0 (2)	C5—C6—N1—O3	178.35 (19)
C11—C7—C8—C9	−179.6 (2)	C11—C12—N2—O5	178.7 (2)
C7—C8—C9—C10	−0.1 (3)	C11—C12—N2—O6	−1.9 (3)
C8—C9—C10—O4	0.1 (3)	C17—C18—N3—O9	2.5 (3)
C8—C7—C11—C12	177.2 (2)	C17—C18—N3—O8	−178.20 (19)
O4—C7—C11—C12	−2.4 (3)	C23—C24—N4—O11	−1.3 (3)
C7—C11—C12—N2	−179.95 (18)	C23—C24—N4—O12	178.77 (19)
O7—C13—C14—C15	−0.2 (2)	C29—C30—N5—O15	178.5 (2)
C17—C13—C14—C15	−179.2 (2)	C29—C30—N5—O14	−1.9 (3)
C13—C14—C15—C16	0.3 (2)	C35—C36—N6—O17	0.9 (3)
C14—C15—C16—O7	−0.3 (3)	C35—C36—N6—O18	−179.32 (19)
C14—C13—C17—C18	179.2 (2)	C2—C1—O1—C4	−0.1 (2)
O7—C13—C17—C18	0.3 (3)	C3—C4—O1—C1	−0.2 (2)
C13—C17—C18—N3	−178.25 (18)	C5—C4—O1—C1	179.84 (17)
O10—C19—C20—C21	0.4 (2)	C9—C10—O4—C7	0.0 (2)
C23—C19—C20—C21	−177.6 (2)	C8—C7—O4—C10	0.0 (2)
C19—C20—C21—C22	−0.5 (2)	C11—C7—O4—C10	179.69 (18)
C20—C21—C22—O10	0.3 (3)	C15—C16—O7—C13	0.2 (2)
C20—C19—C23—C24	174.8 (2)	C14—C13—O7—C16	0.0 (2)
O10—C19—C23—C24	−3.0 (3)	C17—C13—O7—C16	179.15 (18)
C19—C23—C24—N4	−179.47 (18)	C21—C22—O10—C19	−0.1 (2)
O13—C25—C26—C27	0.2 (2)	C20—C19—O10—C22	−0.2 (2)
C29—C25—C26—C27	179.0 (2)	C23—C19—O10—C22	178.11 (17)
C25—C26—C27—C28	−0.1 (3)	C26—C25—O13—C28	−0.3 (2)
C26—C27—C28—O13	−0.1 (3)	C29—C25—O13—C28	−179.25 (19)
C26—C25—C29—C30	−175.2 (2)	C27—C28—O13—C25	0.3 (3)
O13—C25—C29—C30	3.4 (3)	C32—C31—O16—C34	0.1 (2)
C25—C29—C30—N5	−179.79 (18)	C35—C31—O16—C34	179.92 (18)
O16—C31—C32—C33	−0.1 (2)	C33—C34—O16—C31	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O10i	0.93	2.58	3.382 (3)	145
C16—H16···O13	0.93	2.60	3.370 (3)	141
C26—H26···O14ii	0.93	2.59	3.281 (3)	131
C28—H28···O8iii	0.93	2.59	3.405 (3)	146
C34—H34···O4	0.93	2.59	3.383 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O10i	0.93	2.58	3.382 (3)	145
C16—H16⋯O13	0.93	2.60	3.370 (3)	141
C26—H26⋯O14ii	0.93	2.59	3.281 (3)	131
C28—H28⋯O8iii	0.93	2.59	3.405 (3)	146
C34—H34⋯O4	0.93	2.59	3.383 (3)	143

Symmetry codes: (i) ; (ii) ; (iii) .