3-Nitro­acetanilide

The title compound, also known as N-(3-nitro­phenyl)­acet­amide, C₈H₈N₂O₃, is an organic non-linear optical material. It crystallizes in the monoclinic system in the chiral space group P2₁, and there are four independent mol­ecules in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.154
• Data-to-parameter ratio = 14.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.99
         From the CIF: _reflns_number_total               6994
         Count of symmetry unique reflns         4223
         Completeness (_total/calc)            165.62%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      2771
         Fraction of Friedel pairs measured     0.656
         Are heavy atom types Z>Si present           no
          ALERT: MoKa measured Friedel data cannot be used to
                 determine absolute structure in a light-atom
                 study EXCEPT under VERY special conditions.
                 It is preferred that Friedel data is merged in such cases.

---

S1. Comment

The title compound, (I), is found to be of interest as an organic non-linear optical (NLO) material. The crystals show optical second harmonic generation with the fundamental beam (λ = 1064 nm) of Nd–YAG laser. The single-crystal structure elucidation further reinforces this observation.

Fig. 1 shows the title compound. The torsion angles about the C(phenyl)—N(amide) and C(phenyl)-N–(nitro) bonds shows that the amide and nitro groups are along the plane of the phenyl ring (Table 1). The carbonyl group is involved in hydrogen bonding, unlike the case of 2-nitroacetanilide (Kashino et al., 1986). The packing in (I) is stabilized by N—H···O and C—H···O hydrogen bonds (Fig. 2 and Table 2).

S2. Experimental

The title compound was prepared by the direct reaction of 3-nitroaniline and acetic anyhdride at room tempertaure for 10 min. Crystals of (I), suitable for single-crystal diffraction study, were grown at ambient temperature by slow evaporation of a methanol solution.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: PLATON (Spek, 1990).

Figures

	Fig. 1. View of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram of the title compound, viewed down the b axis.

N-[3-nitrophenyl]acetamide

Crystal data

C8H8N2O3	F(000) = 752
Mr = 180.16	Dx = 1.425 Mg m^−3
Monoclinic, P21	Melting point: 428 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 9.767 (2) Å	Cell parameters from 1024 reflections
b = 13.298 (3) Å	θ = 2.2–27.6°
c = 13.272 (3) Å	µ = 0.11 mm^−1
β = 102.991 (5)°	T = 293 K
V = 1679.8 (6) Å^3	Pyramidal, pale orange
Z = 8	0.39 × 0.35 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer	5863 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 28.0°, θmin = 2.1°
ϕ and ω scans	h = −12→12
14297 measured reflections	k = −17→16
6994 independent reflections	l = −17→17

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)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.154	w = 1/[σ^2(Fo^2) + (0.1044P)^2 + 0.024P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
6994 reflections	Δρmax = 0.35 e Å^−3
473 parameters	Δρmin = −0.45 e Å^−3
1 restraint	Absolute structure: (Flack, 1983), 817 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (10)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.40737 (15)	−0.12836 (15)	0.59043 (16)	0.0615 (6)
O2	0.5769 (2)	0.18262 (18)	0.61497 (19)	0.0757 (8)
O3	0.4883 (3)	0.32085 (18)	0.6499 (2)	0.0908 (9)
N1	0.18951 (18)	−0.07173 (14)	0.59296 (15)	0.0448 (6)
N2	0.4811 (2)	0.23191 (18)	0.63255 (17)	0.0554 (7)
C1	0.2156 (2)	0.02897 (16)	0.61683 (17)	0.0402 (7)
C2	0.3408 (2)	0.07837 (18)	0.61529 (17)	0.0417 (7)
C3	0.3483 (2)	0.18004 (18)	0.63493 (18)	0.0436 (7)
C4	0.2398 (3)	0.2365 (2)	0.6551 (2)	0.0567 (9)
C5	0.1173 (3)	0.1858 (2)	0.6579 (2)	0.0609 (9)
C6	0.1049 (3)	0.08470 (19)	0.6393 (2)	0.0542 (8)
C7	0.2823 (2)	−0.14436 (18)	0.57975 (18)	0.0466 (7)
C8	0.2182 (2)	−0.2456 (2)	0.5525 (2)	0.0590 (8)
O4	0.55675 (19)	−0.05282 (18)	0.1092 (2)	0.0804 (8)
O5	1.0841 (2)	0.30344 (19)	0.1431 (2)	0.0810 (9)
O6	0.9631 (3)	0.43087 (18)	0.1721 (2)	0.0904 (10)
N3	0.76854 (19)	0.01203 (16)	0.10646 (16)	0.0501 (6)
N4	0.9766 (2)	0.34116 (19)	0.15559 (17)	0.0609 (8)
C9	0.7508 (2)	0.11361 (19)	0.12941 (17)	0.0427 (7)
C10	0.8666 (2)	0.17544 (19)	0.13413 (18)	0.0453 (7)
C11	0.8534 (2)	0.2766 (2)	0.15133 (17)	0.0464 (7)
C12	0.7304 (3)	0.3204 (2)	0.1643 (2)	0.0556 (8)
C13	0.6178 (3)	0.2572 (3)	0.1622 (2)	0.0613 (9)
C14	0.6272 (3)	0.1552 (2)	0.1452 (2)	0.0560 (9)
C15	0.6742 (2)	−0.0633 (2)	0.0955 (2)	0.0523 (8)
C16	0.7256 (3)	−0.1619 (2)	0.0629 (3)	0.0644 (9)
O7	0.08930 (15)	0.35198 (14)	0.40532 (16)	0.0618 (6)
O8	−0.0786 (2)	0.04216 (18)	0.3677 (2)	0.0815 (9)
O9	0.0097 (3)	−0.09399 (17)	0.3273 (2)	0.0926 (10)
N5	0.30552 (18)	0.30065 (15)	0.39430 (16)	0.0472 (6)
N6	0.0192 (2)	−0.00567 (17)	0.34860 (16)	0.0546 (7)
C17	0.2826 (2)	0.19893 (17)	0.37088 (16)	0.0407 (6)
C18	0.1565 (2)	0.14871 (17)	0.36811 (17)	0.0410 (6)
C19	0.1522 (2)	0.04701 (18)	0.34935 (17)	0.0436 (7)
C20	0.2643 (3)	−0.00889 (19)	0.33469 (18)	0.0506 (8)
C21	0.3879 (3)	0.0427 (2)	0.3357 (2)	0.0587 (9)
C22	0.3962 (2)	0.14423 (19)	0.3528 (2)	0.0498 (8)
C23	0.2141 (2)	0.37025 (19)	0.41255 (19)	0.0462 (7)
C24	0.2760 (3)	0.4722 (2)	0.4417 (3)	0.0653 (9)
O10	0.04660 (17)	0.95677 (17)	0.08361 (18)	0.0710 (7)
O11	0.5722 (2)	0.6000 (2)	0.1172 (2)	0.0830 (9)
O12	0.4545 (3)	0.47362 (19)	0.1525 (2)	0.0998 (10)
N7	0.26410 (19)	0.89451 (16)	0.09509 (16)	0.0495 (6)
N8	0.4658 (2)	0.56315 (19)	0.13404 (18)	0.0623 (8)
C25	0.2456 (2)	0.79236 (17)	0.11558 (17)	0.0433 (7)
C26	0.3586 (2)	0.72909 (18)	0.11594 (16)	0.0442 (7)
C27	0.3446 (3)	0.62859 (19)	0.13368 (18)	0.0475 (7)
C28	0.2233 (3)	0.5863 (2)	0.1507 (2)	0.0574 (9)
C29	0.1138 (3)	0.6502 (2)	0.1521 (2)	0.0632 (10)
C30	0.1220 (2)	0.7513 (2)	0.1357 (2)	0.0557 (8)
C31	0.1684 (2)	0.96886 (19)	0.07988 (19)	0.0505 (8)
C32	0.2229 (3)	1.0694 (2)	0.0566 (2)	0.0627 (9)
H1	0.10368	−0.09081	0.58554	0.0537*
H2	0.41709	0.04364	0.60139	0.0500*
H4	0.24844	0.30550	0.66630	0.0680*
H5	0.04187	0.22099	0.67265	0.0731*
H6	0.02123	0.05240	0.64175	0.0651*
H8A	0.26080	−0.27666	0.50185	0.0886*
H8B	0.11909	−0.23830	0.52475	0.0886*
H8C	0.23350	−0.28682	0.61337	0.0886*
H3	0.85059	−0.00424	0.09832	0.0601*
H10	0.95148	0.14895	0.12582	0.0543*
H12	0.72377	0.38937	0.17397	0.0667*
H13	0.53394	0.28373	0.17247	0.0736*
H14	0.54994	0.11414	0.14441	0.0672*
H16A	0.76729	−0.20048	0.12316	0.0964*
H16B	0.79432	−0.14975	0.02279	0.0964*
H16C	0.64797	−0.19854	0.02201	0.0964*
H5A	0.38962	0.32176	0.39751	0.0567*
H18	0.07790	0.18294	0.37863	0.0492*
H20	0.25756	−0.07808	0.32456	0.0608*
H21	0.46586	0.00802	0.32466	0.0704*
H22	0.47975	0.17750	0.35223	0.0598*
H24A	0.25511	0.51560	0.38236	0.0979*
H24B	0.37600	0.46637	0.46563	0.0979*
H24C	0.23650	0.49995	0.49559	0.0979*
H7	0.34785	0.91179	0.09184	0.0594*
H26	0.44244	0.75449	0.10433	0.0531*
H28	0.21601	0.51748	0.16089	0.0689*
H29	0.03095	0.62385	0.16454	0.0759*
H30	0.04601	0.79267	0.13798	0.0668*
H32A	0.15750	1.09981	−0.00012	0.0938*
H32B	0.31201	1.06106	0.03844	0.0938*
H32C	0.23418	1.11179	0.11641	0.0938*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0371 (8)	0.0450 (10)	0.1060 (14)	0.0007 (7)	0.0234 (8)	−0.0044 (10)
O2	0.0564 (11)	0.0669 (14)	0.1081 (16)	−0.0193 (10)	0.0277 (10)	−0.0021 (12)
O3	0.0900 (15)	0.0435 (13)	0.134 (2)	−0.0239 (11)	0.0149 (14)	0.0014 (12)
N1	0.0358 (9)	0.0343 (10)	0.0667 (12)	−0.0031 (7)	0.0167 (8)	0.0004 (8)
N2	0.0602 (12)	0.0446 (12)	0.0598 (12)	−0.0150 (10)	0.0099 (9)	0.0058 (9)
C1	0.0382 (10)	0.0345 (12)	0.0501 (12)	0.0016 (8)	0.0143 (8)	0.0051 (9)
C2	0.0404 (10)	0.0370 (12)	0.0494 (12)	0.0004 (9)	0.0139 (8)	0.0033 (9)
C3	0.0483 (11)	0.0349 (12)	0.0480 (12)	−0.0033 (8)	0.0114 (9)	0.0040 (9)
C4	0.0750 (16)	0.0303 (12)	0.0676 (16)	0.0033 (11)	0.0221 (12)	0.0022 (11)
C5	0.0626 (15)	0.0396 (14)	0.0878 (19)	0.0152 (11)	0.0325 (13)	0.0024 (12)
C6	0.0443 (11)	0.0471 (15)	0.0772 (16)	0.0029 (10)	0.0261 (10)	0.0047 (12)
C7	0.0382 (10)	0.0395 (13)	0.0646 (13)	0.0008 (9)	0.0169 (9)	0.0010 (10)
C8	0.0452 (11)	0.0415 (14)	0.0937 (18)	−0.0042 (10)	0.0225 (11)	−0.0141 (13)
O4	0.0459 (9)	0.0611 (13)	0.1435 (19)	−0.0084 (9)	0.0406 (11)	−0.0069 (13)
O5	0.0617 (12)	0.0712 (16)	0.1154 (18)	−0.0193 (11)	0.0311 (11)	0.0006 (13)
O6	0.1096 (18)	0.0473 (13)	0.1191 (19)	−0.0256 (12)	0.0356 (15)	−0.0072 (12)
N3	0.0375 (9)	0.0448 (12)	0.0700 (12)	−0.0034 (8)	0.0165 (8)	0.0015 (9)
N4	0.0682 (14)	0.0509 (14)	0.0648 (14)	−0.0169 (11)	0.0174 (10)	0.0038 (10)
C9	0.0376 (10)	0.0407 (12)	0.0501 (12)	0.0000 (9)	0.0106 (8)	0.0032 (10)
C10	0.0404 (10)	0.0444 (13)	0.0521 (12)	0.0011 (9)	0.0128 (8)	0.0036 (9)
C11	0.0503 (11)	0.0423 (12)	0.0463 (12)	−0.0038 (10)	0.0103 (9)	0.0032 (9)
C12	0.0639 (14)	0.0432 (14)	0.0609 (15)	0.0055 (11)	0.0168 (11)	−0.0032 (11)
C13	0.0535 (13)	0.0600 (17)	0.0737 (16)	0.0148 (12)	0.0210 (12)	−0.0049 (13)
C14	0.0431 (12)	0.0571 (16)	0.0698 (16)	−0.0017 (11)	0.0169 (10)	−0.0049 (12)
C15	0.0381 (10)	0.0485 (14)	0.0714 (15)	−0.0061 (10)	0.0145 (10)	0.0067 (11)
C16	0.0490 (12)	0.0474 (16)	0.099 (2)	−0.0053 (12)	0.0214 (12)	−0.0033 (14)
O7	0.0375 (8)	0.0436 (10)	0.1078 (14)	0.0005 (7)	0.0237 (8)	−0.0040 (9)
O8	0.0568 (11)	0.0646 (14)	0.1298 (19)	−0.0169 (10)	0.0353 (11)	−0.0024 (13)
O9	0.1033 (17)	0.0434 (12)	0.138 (2)	−0.0309 (12)	0.0417 (15)	−0.0144 (13)
N5	0.0352 (8)	0.0375 (10)	0.0702 (12)	−0.0037 (7)	0.0147 (8)	−0.0017 (9)
N6	0.0603 (12)	0.0406 (12)	0.0633 (12)	−0.0146 (10)	0.0147 (9)	0.0043 (10)
C17	0.0416 (10)	0.0338 (11)	0.0466 (11)	0.0013 (8)	0.0098 (8)	0.0040 (9)
C18	0.0359 (9)	0.0350 (12)	0.0528 (12)	0.0021 (8)	0.0115 (8)	0.0022 (9)
C19	0.0495 (12)	0.0359 (12)	0.0442 (12)	−0.0048 (9)	0.0082 (8)	0.0044 (9)
C20	0.0649 (14)	0.0306 (11)	0.0577 (14)	0.0068 (10)	0.0165 (10)	−0.0014 (10)
C21	0.0534 (13)	0.0508 (15)	0.0763 (17)	0.0125 (11)	0.0239 (11)	−0.0036 (13)
C22	0.0397 (10)	0.0452 (14)	0.0670 (15)	0.0007 (9)	0.0174 (9)	−0.0002 (11)
C23	0.0396 (10)	0.0353 (12)	0.0657 (13)	−0.0018 (9)	0.0162 (9)	0.0006 (10)
C24	0.0496 (13)	0.0386 (15)	0.111 (2)	−0.0058 (10)	0.0249 (13)	−0.0123 (14)
O10	0.0389 (9)	0.0615 (12)	0.1161 (16)	0.0030 (8)	0.0247 (9)	0.0052 (11)
O11	0.0651 (12)	0.0815 (17)	0.1091 (17)	0.0214 (12)	0.0334 (12)	0.0002 (13)
O12	0.1023 (18)	0.0497 (15)	0.145 (2)	0.0199 (13)	0.0226 (16)	0.0020 (14)
N7	0.0378 (9)	0.0439 (12)	0.0705 (12)	−0.0036 (8)	0.0202 (8)	−0.0035 (9)
N8	0.0625 (13)	0.0508 (14)	0.0716 (14)	0.0114 (11)	0.0107 (10)	−0.0087 (11)
C25	0.0408 (10)	0.0416 (13)	0.0488 (12)	0.0020 (9)	0.0131 (8)	−0.0053 (9)
C26	0.0362 (10)	0.0478 (13)	0.0502 (12)	−0.0003 (9)	0.0129 (8)	−0.0074 (10)
C27	0.0540 (12)	0.0412 (13)	0.0464 (12)	0.0024 (10)	0.0092 (9)	−0.0095 (10)
C28	0.0667 (15)	0.0429 (14)	0.0643 (16)	−0.0084 (12)	0.0186 (12)	−0.0040 (11)
C29	0.0553 (14)	0.0558 (17)	0.0846 (19)	−0.0143 (12)	0.0287 (13)	−0.0045 (14)
C30	0.0399 (11)	0.0545 (16)	0.0770 (16)	−0.0007 (10)	0.0224 (10)	−0.0030 (13)
C31	0.0412 (11)	0.0487 (14)	0.0641 (14)	0.0006 (10)	0.0171 (10)	−0.0024 (11)
C32	0.0481 (12)	0.0488 (15)	0.094 (2)	0.0044 (11)	0.0219 (12)	0.0109 (13)

Geometric parameters (Å, º)

O1—C7	1.216 (3)	C9—C14	1.386 (4)
O2—N2	1.207 (3)	C9—C10	1.388 (3)
O3—N2	1.204 (3)	C10—C11	1.375 (4)
O4—C15	1.209 (3)	C11—C12	1.380 (4)
O5—N4	1.208 (3)	C12—C13	1.379 (4)
O6—N4	1.225 (3)	C13—C14	1.381 (5)
O7—C23	1.225 (3)	C15—C16	1.502 (4)
O8—N6	1.221 (3)	C10—H10	0.9299
O9—N6	1.207 (3)	C12—H12	0.9304
O10—C31	1.212 (3)	C13—H13	0.9296
O11—N8	1.214 (3)	C14—H14	0.9296
O12—N8	1.225 (4)	C16—H16A	0.9603
N1—C1	1.386 (3)	C16—H16C	0.9601
N1—C7	1.362 (3)	C16—H16B	0.9595
N2—C3	1.476 (3)	C17—C18	1.394 (3)
N1—H1	0.8601	C17—C22	1.392 (3)
N3—C9	1.404 (3)	C18—C19	1.374 (3)
N3—C15	1.347 (3)	C19—C20	1.373 (4)
N4—C11	1.469 (3)	C20—C21	1.386 (4)
N3—H3	0.8600	C21—C22	1.368 (4)
N5—C23	1.345 (3)	C23—C24	1.499 (4)
N5—C17	1.395 (3)	C18—H18	0.9296
N6—C19	1.474 (3)	C20—H20	0.9301
N5—H5A	0.8600	C21—H21	0.9296
N7—C31	1.344 (3)	C22—H22	0.9298
N7—C25	1.405 (3)	C24—H24A	0.9606
N8—C27	1.468 (4)	C24—H24C	0.9595
N7—H7	0.8600	C24—H24B	0.9599
C1—C2	1.392 (3)	C25—C30	1.404 (3)
C1—C6	1.397 (4)	C25—C26	1.387 (3)
C2—C3	1.376 (3)	C26—C27	1.369 (3)
C3—C4	1.373 (4)	C27—C28	1.375 (4)
C4—C5	1.381 (4)	C28—C29	1.369 (4)
C5—C6	1.367 (4)	C29—C30	1.367 (4)
C7—C8	1.494 (4)	C31—C32	1.497 (4)
C2—H2	0.9297	C26—H26	0.9301
C4—H4	0.9303	C28—H28	0.9302
C5—H5	0.9300	C29—H29	0.9300
C6—H6	0.9302	C30—H30	0.9298
C8—H8A	0.9599	C32—H32A	0.9602
C8—H8B	0.9601	C32—H32B	0.9603
C8—H8C	0.9598	C32—H32C	0.9595
O1···C2	2.861 (3)	C18···C2	3.496 (3)
O1···N5^i	2.922 (3)	C18···C1	3.593 (3)
O2···C27^i	3.329 (3)	C18···O7	2.851 (3)
O2···C24^i	3.308 (4)	C19···C1	3.472 (3)
O3···C21^ii	3.178 (4)	C20···C31^iii	3.313 (3)
O3···C20^ii	3.284 (4)	C20···O3^i	3.284 (4)
O3···C26^i	3.361 (3)	C20···N7^iii	3.429 (3)
O4···C14	2.865 (4)	C21···O3^i	3.178 (4)
O4···N7^iii	2.908 (3)	C24···O2^ii	3.308 (4)
O6···C6^ii	3.412 (4)	C25···C11^x	3.462 (3)
O6···C31^iv	3.340 (4)	C26···C9^x	3.541 (3)
O6···C28^v	3.337 (4)	C26···O3^ii	3.361 (3)
O6···C29^v	3.304 (4)	C26···N2^ii	3.353 (3)
O6···O7^v	3.238 (3)	C27···C9^x	3.411 (3)
O7···C18	2.851 (3)	C27···O2^ii	3.329 (3)
O7···N1^vi	2.911 (3)	C28···O6^vii	3.337 (4)
O7···N4^vii	3.252 (3)	C29···O6^vii	3.304 (4)
O7···O6^vii	3.238 (3)	C30···O10	2.874 (4)
O8···C8^vi	3.405 (4)	C31···C20^xiii	3.313 (3)
O8···C9^vii	3.363 (3)	C31···O6^x	3.340 (4)
O9···C4^viii	3.366 (4)	C32···O11^x	3.401 (4)
O9···C5^viii	3.203 (4)	C4···H16A^ii	3.0756
O10···N3^ix	2.894 (3)	C7···H2	2.8099
O10···C30	2.874 (4)	C13···H8C^ii	3.0626
O11···C3^ii	3.378 (4)	C15···H14	2.7957
O11···C32^iv	3.401 (4)	C21···H32C^iii	3.0991
O12···C15^x	3.286 (4)	C23···H18	2.8120
O12···C13	3.279 (5)	C24···H6^vi	3.0572
O12···C12	3.354 (4)	C29···H32A^xiv	3.0226
O1···H2	2.2925	C31···H30	2.8156
O1···H22^i	2.8430	H1···O7^viii	2.0613
O1···H24B^i	2.7065	H1···H6	2.2587
O1···H5A^i	2.0626	H1···H8B	2.1389
O2···H2	2.3996	H2···H24B^i	2.5960
O2···H8A^ii	2.5129	H2···O2	2.3996
O2···H24A^i	2.7568	H2···C7	2.8099
O3···H4	2.4097	H2···O1	2.2925
O3···H21^ii	2.5380	H3···H16B	2.1917
O3···H20^ii	2.7757	H3···H10	2.2566
O4···H7^iii	2.0558	H3···O10^xii	2.0347
O4···H26^iii	2.7900	H4···O3	2.4097
O4···H14	2.2729	H4···O9^vi	2.8717
O4···H32B^iii	2.8071	H5···O9^vi	2.5115
O5···H10	2.4119	H5A···O1^ii	2.0626
O5···H16B^xi	2.7965	H5A···H24B	2.1418
O6···H29^v	2.6580	H5A···H22	2.2481
O6···H28^v	2.7596	H6···O7^viii	2.8906
O6···H12	2.4073	H6···H1	2.2587
O7···H6^vi	2.8906	H6···C24^viii	3.0572
O7···H8B^vi	2.7009	H7···H32B	2.1103
O7···H1^vi	2.0613	H7···O4^xiii	2.0558
O7···H18	2.2745	H7···H26	2.2776
O8···H24C^viii	2.6914	H8A···O2^i	2.5129
O8···H8C^vi	2.7740	H8B···O7^viii	2.7009
O8···H18	2.4005	H8B···H1	2.1389
O9···H20	2.4385	H8C···O8^viii	2.7740
O9···H4^viii	2.8717	H8C···C13^i	3.0626
O9···H5^viii	2.5115	H10···H3	2.2566
O10···H30	2.2988	H10···O10^xii	2.8182
O10···H3^ix	2.0347	H10···O5	2.4119
O10···H16B^ix	2.7991	H12···O6	2.4073
O10···H10^ix	2.8182	H12···O12	2.8136
O11···H26	2.3997	H13···O12	2.6375
O11···H32B^iv	2.6200	H14···O4	2.2729
O12···H13	2.6375	H14···C15	2.7957
O12···H12	2.8136	H14···H32B^iii	2.5312
O12···H28	2.4280	H16A···C4^i	3.0756
N1···O7^viii	2.911 (3)	H16B···O5^xv	2.7965
N2···C26^i	3.353 (3)	H16B···O10^xii	2.7991
N3···O10^xii	2.894 (3)	H16B···H3	2.1917
N4···O7^v	3.252 (3)	H16C···H26^iii	2.5690
N5···O1^ii	2.922 (3)	H18···O7	2.2745
N7···C20^xiii	3.429 (3)	H18···C23	2.8120
N7···O4^xiii	2.908 (3)	H18···O8	2.4005
N8···C2^ii	3.443 (3)	H20···O3^i	2.7757
C1···C19	3.472 (3)	H20···O9	2.4385
C1···C18	3.593 (3)	H21···O3^i	2.5380
C2···O1	2.861 (3)	H22···O1^ii	2.8430
C2···C17	3.548 (3)	H22···H5A	2.2481
C2···C18	3.496 (3)	H24A···O2^ii	2.7568
C2···N8^i	3.443 (3)	H24B···H2^ii	2.5960
C3···C17	3.427 (3)	H24B···H5A	2.1418
C3···O11^i	3.378 (4)	H24B···O1^ii	2.7065
C4···O9^vi	3.366 (4)	H24C···O8^vi	2.6914
C5···O9^vi	3.203 (4)	H26···O4^xiii	2.7900
C6···O6^i	3.412 (4)	H26···O11	2.3997
C7···C12^i	3.459 (4)	H26···H7	2.2776
C7···C13^i	3.591 (4)	H26···H16C^xiii	2.5690
C8···O8^viii	3.405 (4)	H28···O6^vii	2.7596
C9···C27^iv	3.411 (3)	H28···O12	2.4280
C9···C26^iv	3.541 (3)	H29···O6^vii	2.6580
C9···O8^v	3.363 (3)	H29···H32A^xiv	2.5389
C11···C25^iv	3.462 (3)	H30···O10	2.2988
C12···C7^ii	3.459 (4)	H30···C31	2.8156
C12···O12	3.354 (4)	H32A···C29^xvi	3.0226
C13···O12	3.279 (5)	H32A···H29^xvi	2.5389
C13···C7^ii	3.591 (4)	H32B···O4^xiii	2.8071
C14···O4	2.865 (4)	H32B···H7	2.1103
C15···O12^iv	3.286 (4)	H32B···H14^xiii	2.5312
C17···C2	3.548 (3)	H32B···O11^x	2.6200
C17···C3	3.427 (3)	H32C···C21^xiii	3.0991
C1—N1—C7	128.37 (19)	C11—C12—H12	121.52
O2—N2—O3	123.8 (3)	C13—C12—H12	121.57
O2—N2—C3	118.3 (2)	C12—C13—H13	119.38
O3—N2—C3	118.0 (2)	C14—C13—H13	119.32
C7—N1—H1	115.82	C13—C14—H14	119.67
C1—N1—H1	115.81	C9—C14—H14	119.76
C9—N3—C15	128.63 (19)	C15—C16—H16A	109.45
O6—N4—C11	117.1 (2)	C15—C16—H16B	109.49
O5—N4—C11	118.8 (2)	C15—C16—H16C	109.46
O5—N4—O6	124.1 (3)	H16A—C16—H16B	109.48
C15—N3—H3	115.69	H16B—C16—H16C	109.50
C9—N3—H3	115.67	H16A—C16—H16C	109.44
C17—N5—C23	128.87 (19)	N5—C17—C18	124.54 (19)
O8—N6—O9	122.2 (2)	C18—C17—C22	118.6 (2)
O8—N6—C19	118.7 (2)	N5—C17—C22	116.81 (19)
O9—N6—C19	119.0 (2)	C17—C18—C19	117.84 (19)
C23—N5—H5A	115.58	N6—C19—C20	118.1 (2)
C17—N5—H5A	115.55	N6—C19—C18	117.39 (19)
C25—N7—C31	128.67 (19)	C18—C19—C20	124.5 (2)
O12—N8—C27	117.9 (2)	C19—C20—C21	116.8 (2)
O11—N8—O12	123.2 (3)	C20—C21—C22	120.6 (3)
O11—N8—C27	118.9 (2)	C17—C22—C21	121.6 (2)
C31—N7—H7	115.66	N5—C23—C24	115.0 (2)
C25—N7—H7	115.67	O7—C23—N5	122.6 (2)
C2—C1—C6	118.5 (2)	O7—C23—C24	122.4 (2)
N1—C1—C2	124.70 (19)	C19—C18—H18	121.10
N1—C1—C6	116.7 (2)	C17—C18—H18	121.06
C1—C2—C3	118.06 (19)	C21—C20—H20	121.62
N2—C3—C4	118.0 (2)	C19—C20—H20	121.56
N2—C3—C2	117.71 (19)	C22—C21—H21	119.70
C2—C3—C4	124.3 (2)	C20—C21—H21	119.70
C3—C4—C5	116.7 (2)	C17—C22—H22	119.20
C4—C5—C6	121.1 (3)	C21—C22—H22	119.18
C1—C6—C5	121.2 (3)	H24A—C24—H24C	109.46
O1—C7—N1	122.7 (2)	H24B—C24—H24C	109.52
N1—C7—C8	114.53 (18)	C23—C24—H24A	109.43
O1—C7—C8	122.7 (2)	C23—C24—H24B	109.49
C1—C2—H2	120.95	H24A—C24—H24B	109.43
C3—C2—H2	120.99	C23—C24—H24C	109.50
C3—C4—H4	121.61	N7—C25—C30	124.5 (2)
C5—C4—H4	121.68	C26—C25—C30	118.7 (2)
C6—C5—H5	119.38	N7—C25—C26	116.76 (19)
C4—C5—H5	119.48	C25—C26—C27	118.9 (2)
C5—C6—H6	119.38	N8—C27—C28	118.7 (2)
C1—C6—H6	119.38	N8—C27—C26	117.9 (2)
C7—C8—H8A	109.46	C26—C27—C28	123.4 (3)
C7—C8—H8B	109.46	C27—C28—C29	116.9 (2)
H8A—C8—H8B	109.47	C28—C29—C30	122.3 (3)
H8A—C8—H8C	109.50	C25—C30—C29	119.8 (2)
C7—C8—H8C	109.47	N7—C31—C32	114.9 (2)
H8B—C8—H8C	109.48	O10—C31—N7	123.5 (2)
N3—C9—C14	124.8 (2)	O10—C31—C32	121.6 (2)
C10—C9—C14	119.0 (2)	C25—C26—H26	120.57
N3—C9—C10	116.14 (19)	C27—C26—H26	120.57
C9—C10—C11	118.7 (2)	C27—C28—H28	121.54
C10—C11—C12	123.4 (2)	C29—C28—H28	121.53
N4—C11—C12	118.5 (2)	C28—C29—H29	118.82
N4—C11—C10	118.13 (19)	C30—C29—H29	118.90
C11—C12—C13	116.9 (3)	C25—C30—H30	120.18
C12—C13—C14	121.3 (3)	C29—C30—H30	120.06
C9—C14—C13	120.6 (3)	C31—C32—H32A	109.47
O4—C15—N3	123.2 (3)	C31—C32—H32B	109.46
N3—C15—C16	114.6 (2)	C31—C32—H32C	109.51
O4—C15—C16	122.3 (2)	H32A—C32—H32B	109.43
C11—C10—H10	120.63	H32A—C32—H32C	109.49
C9—C10—H10	120.62	H32B—C32—H32C	109.48
C7—N1—C1—C2	11.1 (4)	C1—C2—C3—N2	−179.7 (2)
C7—N1—C1—C6	−171.9 (2)	C1—C2—C3—C4	−0.6 (4)
C1—N1—C7—C8	−179.0 (2)	C2—C3—C4—C5	1.6 (4)
C1—N1—C7—O1	1.8 (4)	N2—C3—C4—C5	−179.4 (2)
O3—N2—C3—C4	1.1 (3)	C3—C4—C5—C6	−1.3 (4)
O2—N2—C3—C2	−1.0 (3)	C4—C5—C6—C1	0.0 (4)
O2—N2—C3—C4	179.9 (2)	N3—C9—C14—C13	−176.7 (2)
O3—N2—C3—C2	−179.8 (2)	C14—C9—C10—C11	−1.9 (3)
C9—N3—C15—C16	175.6 (3)	C10—C9—C14—C13	2.0 (4)
C15—N3—C9—C10	−178.8 (2)	N3—C9—C10—C11	176.9 (2)
C15—N3—C9—C14	−0.1 (4)	C9—C10—C11—C12	0.0 (4)
C9—N3—C15—O4	−3.4 (4)	C9—C10—C11—N4	−179.7 (2)
O6—N4—C11—C12	1.0 (3)	N4—C11—C12—C13	−178.6 (2)
O5—N4—C11—C12	−179.2 (2)	C10—C11—C12—C13	1.7 (4)
O5—N4—C11—C10	0.6 (3)	C11—C12—C13—C14	−1.6 (4)
O6—N4—C11—C10	−179.2 (2)	C12—C13—C14—C9	−0.2 (4)
C23—N5—C17—C22	178.3 (2)	N5—C17—C18—C19	−176.5 (2)
C17—N5—C23—C24	176.6 (2)	N5—C17—C22—C21	175.8 (2)
C17—N5—C23—O7	−3.8 (4)	C18—C17—C22—C21	−2.0 (4)
C23—N5—C17—C18	−4.0 (4)	C22—C17—C18—C19	1.1 (3)
O9—N6—C19—C18	176.4 (2)	C17—C18—C19—C20	1.0 (3)
O9—N6—C19—C20	−5.7 (3)	C17—C18—C19—N6	178.84 (19)
O8—N6—C19—C20	175.7 (2)	C18—C19—C20—C21	−2.3 (4)
O8—N6—C19—C18	−2.3 (3)	N6—C19—C20—C21	179.9 (2)
C31—N7—C25—C26	172.5 (2)	C19—C20—C21—C22	1.3 (4)
C25—N7—C31—C32	−178.3 (2)	C20—C21—C22—C17	0.8 (4)
C25—N7—C31—O10	1.2 (4)	N7—C25—C30—C29	178.3 (2)
C31—N7—C25—C30	−7.7 (4)	C30—C25—C26—C27	1.4 (3)
O12—N8—C27—C28	−2.0 (4)	N7—C25—C26—C27	−178.8 (2)
O11—N8—C27—C28	178.7 (3)	C26—C25—C30—C29	−1.9 (4)
O11—N8—C27—C26	−1.1 (4)	C25—C26—C27—C28	0.4 (4)
O12—N8—C27—C26	178.2 (2)	C25—C26—C27—N8	−179.8 (2)
N1—C1—C6—C5	−176.2 (2)	C26—C27—C28—C29	−1.7 (4)
C6—C1—C2—C3	−0.7 (3)	N8—C27—C28—C29	178.5 (2)
N1—C1—C2—C3	176.2 (2)	C27—C28—C29—C30	1.1 (4)
C2—C1—C6—C5	1.0 (4)	C28—C29—C30—C25	0.6 (4)

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+1, y+1/2, −z+1; (iii) x, y−1, z; (iv) −x+1, y−1/2, −z; (v) x+1, y, z; (vi) −x, y+1/2, −z+1; (vii) x−1, y, z; (viii) −x, y−1/2, −z+1; (ix) x−1, y+1, z; (x) −x+1, y+1/2, −z; (xi) −x+2, y+1/2, −z; (xii) x+1, y−1, z; (xiii) x, y+1, z; (xiv) −x, y−1/2, −z; (xv) −x+2, y−1/2, −z; (xvi) −x, y+1/2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O7^viii	0.86	2.06	2.911 (3)	169
N3—H3···O10^xii	0.86	2.03	2.894 (3)	178
N5—H5A···O1^ii	0.86	2.06	2.922 (3)	178
N7—H7···O4^xiii	0.86	2.06	2.908 (3)	171
C2—H2···O1	0.93	2.29	2.861 (3)	119
C5—H5···O9^vi	0.93	2.51	3.203 (4)	131
C8—H8A···O2^i	0.96	2.51	3.443 (3)	163
C14—H14···O4	0.93	2.27	2.865 (4)	121
C18—H18···O7	0.93	2.27	2.851 (3)	120
C21—H21···O3^i	0.93	2.54	3.178 (4)	126
C30—H30···O10	0.93	2.30	2.874 (4)	120

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+1, y+1/2, −z+1; (vi) −x, y+1/2, −z+1; (viii) −x, y−1/2, −z+1; (xii) x+1, y−1, z; (xiii) x, y+1, z.