Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
3-Nitroacetanilide
L. Mahalakshmi,aV. Upadhyayab and T. N. Guru Rowa*
aSolid State and Structural Chemistry Unit,
Indian Institute of Science, Bangalore 560 012, India, andbPhysics Department, Manipal
Institute of Technology, Manipal 576 119, India
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 293 K
Mean(C±C) = 0.004 AÊ
Rfactor = 0.059
wRfactor = 0.154
Data-to-parameter ratio = 14.8
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
The title compound, also known as N -(3-nitrophenyl)acet-amide, 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.
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 (= 1064 nm) of Nd±YAG laser. The single-crystal structure elucidation further reinforces this observation.
Fig. 1 shows the asymmetric unit of the title compound. The torsion angles about the C(phenyl)ÐN(amide) and C(phenyl)ÐN(nitro) bonds show that the amide and nitro groups lie in the plane of the phenyl ring (Table 1). The carbonyl group is involved in hydrogen bonding, unlike the case of 2-nitroacetanilide (Kashinoet al., 1986). The packing in (I) is stabilized by NÐH O and CÐH O hydrogen bonds (Fig. 2 and Table 2).
Experimental
The title compound was prepared by the direct reaction of 3-nitro-aniline and acetic anhydride at room temperature for 10 min. Crystals of (I), suitable for single-crystal diffraction study, were grown at ambient temperature by slow evaporation of a methanol solution. Crystal data
C8H8N2O3
Mr= 180.16
Monoclinic,P21
a= 9.767 (2) AÊ
b= 13.298 (3) AÊ
c= 13.272 (3) AÊ
= 102.991 (5)
V= 1679.8 (6) AÊ3
Z= 8
Dx= 1.425 Mg mÿ3
MoKradiation Cell parameters from 1024
re¯ections
= 2.2±27.6 = 0.11 mmÿ1
T= 293 (2) K Pyramid, pale orange 0.390.350.16 mm
Data collection
Bruker SMART CCD area-detector diffractometer
'and!scans
Absorption correction: none
5863 re¯ections withI> 2(I)
Rint= 0.026
max= 28.0
h=ÿ12!12
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.059
wR(F2) = 0.154
S= 1.07 6994 re¯ections 473 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.1044P)2
+ 0.024P]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001 max= 0.35 e AÊÿ3 min=ÿ0.45 e AÊÿ3
Absolute structure: (Flack, 1983), 817 Friedel pairs
Flack parameter =ÿ0.01 (10)
Table 1
Selected geometric parameters (AÊ,).
O1ÐC7 1.216 (3) O2ÐN2 1.207 (3) O3ÐN2 1.204 (3) O4ÐC15 1.209 (3) O5ÐN4 1.208 (3) O6ÐN4 1.225 (3) O7ÐC23 1.225 (3) O8ÐN6 1.221 (3) O9ÐN6 1.207 (3) O10ÐC31 1.212 (3) O11ÐN8 1.214 (3) O12ÐN8 1.225 (4)
N1ÐC1 1.386 (3) N1ÐC7 1.362 (3) N2ÐC3 1.476 (3) N3ÐC9 1.404 (3) N3ÐC15 1.347 (3) N4ÐC11 1.469 (3) N5ÐC23 1.345 (3) N5ÐC17 1.395 (3) N6ÐC19 1.474 (3) N7ÐC31 1.344 (3) N7ÐC25 1.405 (3) N8ÐC27 1.468 (4)
C7ÐN1ÐC1ÐC6 ÿ171.9 (2) C1ÐN1ÐC7ÐC8 ÿ179.0 (2) O2ÐN2ÐC3ÐC4 179.9 (2) O3ÐN2ÐC3ÐC2 ÿ179.8 (2) C9ÐN3ÐC15ÐC16 175.6 (3) O5ÐN4ÐC11ÐC12 ÿ179.2 (2) O6ÐN4ÐC11ÐC10 ÿ179.2 (2) C23ÐN5ÐC17ÐC22 178.3 (2)
C17ÐN5ÐC23ÐC24 176.6 (2) O9ÐN6ÐC19ÐC18 176.4 (2) O8ÐN6ÐC19ÐC20 175.7 (2) C31ÐN7ÐC25ÐC26 172.5 (2) C25ÐN7ÐC31ÐC32 ÿ178.3 (2) O11ÐN8ÐC27ÐC28 178.7 (3) O11ÐN8ÐC27ÐC26 ÿ1.1 (4) O12ÐN8ÐC27ÐC26 178.2 (2)
Table 2
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
N1ÐH1 O7i 0.86 2.06 2.911 (3) 169
N3ÐH3 O10ii 0.86 2.03 2.894 (3) 178
N5ÐH5A O1iii 0.86 2.06 2.922 (3) 178
N7ÐH7 O4iv 0.86 2.06 2.908 (3) 171
C2ÐH2 O1 0.93 2.29 2.861 (3) 119 C5ÐH5 O9v 0.93 2.51 3.203 (4) 131
C8ÐH8A O2vi 0.96 2.51 3.443 (3) 163
C14ÐH14 O4 0.93 2.27 2.865 (4) 121 C18ÐH18 O7 0.93 2.27 2.851 (3) 120 C21ÐH21 O3vi 0.93 2.54 3.178 (4) 126
C30ÐH30 O10 0.93 2.30 2.874 (4) 120
Symmetry codes: (i)ÿx;yÿ1
2;1ÿz; (ii) 1x;yÿ1;z; (iii) 1ÿx;12y;1ÿz; (iv)
x;1y;z; (v)ÿx;1
2y;1ÿz; (vi) 1ÿx;yÿ12;1ÿz.
H atoms were positioned geometrically and allowed to ride on their respective parent atoms; CÐH = 0.93±0.96 AÊ, and Uiso = 1.2Ueq(NH and ring CH) or 1.5Ueq(CH3and CH2).
Data collection:SMART(Bruker, 1998); cell re®nement:SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure:SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) andCAMERON(Watkinet al., 1996); software used to prepare material for publication: PLATON(Spek, 1990).
The authors thank the Department of Science and Tech-nology, India, for data collection on the CCD facility set up
under the IRFA-DST program. LM thanks DST, India, for a research associateship.
References
Bruker (1998).SMARTandSAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997).J. Appl. Cryst.30, 565. Flack, H. D. (1983).Acta Cryst.A39, 876±881.
Kashino, S., Matsushita, T., Iwamoto, T., Yamaguchi, K. & Haisa, M. (1986).
Acta Cryst.C42, 457±462.
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of GoÈttingen, Germany.
Spek, A. L. (1990).Acta Cryst.A46, C-34.
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996).CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.
Figure 1
View of the asymmetric unit of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Figure 2
supporting information
Acta Cryst. (2002). E58, o983–o984 [doi:10.1107/S1600536802013843]
3-Nitroacetanilide
L. Mahalakshmi, V. Upadhyaya and T. N. Guru Row
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
[image:3.610.126.478.408.661.2]of a methanol solution.
Figure 1
View of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability
Figure 2
Packing diagram of the title compound, viewed down the b axis.
N-[3-nitrophenyl]acetamide
Crystal data
C8H8N2O3
Mr = 180.16 Monoclinic, P21
Hall symbol: P 2yb
a = 9.767 (2) Å
b = 13.298 (3) Å
c = 13.272 (3) Å
β = 102.991 (5)°
V = 1679.8 (6) Å3
Z = 8
F(000) = 752
Dx = 1.425 Mg m−3
Melting point: 428 K
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 1024 reflections
θ = 2.2–27.6°
µ = 0.11 mm−1
T = 293 K
Data collection
Bruker SMART CCD area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ and ω scans
14297 measured reflections 6994 independent reflections
5863 reflections with I > 2σ(I)
Rint = 0.026
θmax = 28.0°, θmin = 2.1°
h = −12→12
k = −17→16
l = −17→17
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.059
wR(F2) = 0.154
S = 1.07 6994 reflections 473 parameters 1 restraint
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained
w = 1/[σ2(F
o2) + (0.1044P)2 + 0.024P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.35 e Å−3
Δρmin = −0.45 e Å−3
Absolute structure: (Flack, 1983), 817 Friedel pairs
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 (Å2)
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)
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*
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 (Å2)
U11 U22 U33 U12 U13 U23
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)
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—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···N5i 2.922 (3) C18···C1 3.593 (3)
O2···C27i 3.329 (3) C18···O7 2.851 (3)
O2···C24i 3.308 (4) C19···C1 3.472 (3)
O3···C21ii 3.178 (4) C20···C31iii 3.313 (3)
O3···C20ii 3.284 (4) C20···O3i 3.284 (4)
O3···C26i 3.361 (3) C20···N7iii 3.429 (3)
O4···C14 2.865 (4) C21···O3i 3.178 (4)
O4···N7iii 2.908 (3) C24···O2ii 3.308 (4)
O6···C6ii 3.412 (4) C25···C11x 3.462 (3)
O6···C31iv 3.340 (4) C26···C9x 3.541 (3)
O6···C28v 3.337 (4) C26···O3ii 3.361 (3)
O6···C29v 3.304 (4) C26···N2ii 3.353 (3)
O6···O7v 3.238 (3) C27···C9x 3.411 (3)
O7···C18 2.851 (3) C27···O2ii 3.329 (3)
O7···N1vi 2.911 (3) C28···O6vii 3.337 (4)
O7···N4vii 3.252 (3) C29···O6vii 3.304 (4)
O7···O6vii 3.238 (3) C30···O10 2.874 (4)
O8···C8vi 3.405 (4) C31···C20xiii 3.313 (3)
O8···C9vii 3.363 (3) C31···O6x 3.340 (4)
O9···C4viii 3.366 (4) C32···O11x 3.401 (4)
O10···N3ix 2.894 (3) C7···H2 2.8099
O10···C30 2.874 (4) C13···H8Cii 3.0626
O11···C3ii 3.378 (4) C15···H14 2.7957
O11···C32iv 3.401 (4) C21···H32Ciii 3.0991
O12···C15x 3.286 (4) C23···H18 2.8120
O12···C13 3.279 (5) C24···H6vi 3.0572
O12···C12 3.354 (4) C29···H32Axiv 3.0226
O1···H2 2.2925 C31···H30 2.8156
O1···H22i 2.8430 H1···O7viii 2.0613
O1···H24Bi 2.7065 H1···H6 2.2587
O1···H5Ai 2.0626 H1···H8B 2.1389
O2···H2 2.3996 H2···H24Bi 2.5960
O2···H8Aii 2.5129 H2···O2 2.3996
O2···H24Ai 2.7568 H2···C7 2.8099
O3···H4 2.4097 H2···O1 2.2925
O3···H21ii 2.5380 H3···H16B 2.1917
O3···H20ii 2.7757 H3···H10 2.2566
O4···H7iii 2.0558 H3···O10xii 2.0347
O4···H26iii 2.7900 H4···O3 2.4097
O4···H14 2.2729 H4···O9vi 2.8717
O4···H32Biii 2.8071 H5···O9vi 2.5115
O5···H10 2.4119 H5A···O1ii 2.0626
O5···H16Bxi 2.7965 H5A···H24B 2.1418
O6···H29v 2.6580 H5A···H22 2.2481
O6···H28v 2.7596 H6···O7viii 2.8906
O6···H12 2.4073 H6···H1 2.2587
O7···H6vi 2.8906 H6···C24viii 3.0572
O7···H8Bvi 2.7009 H7···H32B 2.1103
O7···H1vi 2.0613 H7···O4xiii 2.0558
O7···H18 2.2745 H7···H26 2.2776
O8···H24Cviii 2.6914 H8A···O2i 2.5129
O8···H8Cvi 2.7740 H8B···O7viii 2.7009
O8···H18 2.4005 H8B···H1 2.1389
O9···H20 2.4385 H8C···O8viii 2.7740
O9···H4viii 2.8717 H8C···C13i 3.0626
O9···H5viii 2.5115 H10···H3 2.2566
O10···H30 2.2988 H10···O10xii 2.8182
O10···H3ix 2.0347 H10···O5 2.4119
O10···H16Bix 2.7991 H12···O6 2.4073
O10···H10ix 2.8182 H12···O12 2.8136
O11···H26 2.3997 H13···O12 2.6375
O11···H32Biv 2.6200 H14···O4 2.2729
O12···H13 2.6375 H14···C15 2.7957
O12···H12 2.8136 H14···H32Biii 2.5312
O12···H28 2.4280 H16A···C4i 3.0756
N1···O7viii 2.911 (3) H16B···O5xv 2.7965
N2···C26i 3.353 (3) H16B···O10xii 2.7991
N4···O7v 3.252 (3) H16C···H26iii 2.5690
N5···O1ii 2.922 (3) H18···O7 2.2745
N7···C20xiii 3.429 (3) H18···C23 2.8120
N7···O4xiii 2.908 (3) H18···O8 2.4005
N8···C2ii 3.443 (3) H20···O3i 2.7757
C1···C19 3.472 (3) H20···O9 2.4385
C1···C18 3.593 (3) H21···O3i 2.5380
C2···O1 2.861 (3) H22···O1ii 2.8430
C2···C17 3.548 (3) H22···H5A 2.2481
C2···C18 3.496 (3) H24A···O2ii 2.7568
C2···N8i 3.443 (3) H24B···H2ii 2.5960
C3···C17 3.427 (3) H24B···H5A 2.1418
C3···O11i 3.378 (4) H24B···O1ii 2.7065
C4···O9vi 3.366 (4) H24C···O8vi 2.6914
C5···O9vi 3.203 (4) H26···O4xiii 2.7900
C6···O6i 3.412 (4) H26···O11 2.3997
C7···C12i 3.459 (4) H26···H7 2.2776
C7···C13i 3.591 (4) H26···H16Cxiii 2.5690
C8···O8viii 3.405 (4) H28···O6vii 2.7596
C9···C27iv 3.411 (3) H28···O12 2.4280
C9···C26iv 3.541 (3) H29···O6vii 2.6580
C9···O8v 3.363 (3) H29···H32Axiv 2.5389
C11···C25iv 3.462 (3) H30···O10 2.2988
C12···C7ii 3.459 (4) H30···C31 2.8156
C12···O12 3.354 (4) H32A···C29xvi 3.0226
C13···O12 3.279 (5) H32A···H29xvi 2.5389
C13···C7ii 3.591 (4) H32B···O4xiii 2.8071
C14···O4 2.865 (4) H32B···H7 2.1103
C15···O12iv 3.286 (4) H32B···H14xiii 2.5312
C17···C2 3.548 (3) H32B···O11x 2.6200
C17···C3 3.427 (3) H32C···C21xiii 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)
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
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···O7viii 0.86 2.06 2.911 (3) 169
N5—H5A···O1ii 0.86 2.06 2.922 (3) 178
N7—H7···O4xiii 0.86 2.06 2.908 (3) 171
C2—H2···O1 0.93 2.29 2.861 (3) 119
C5—H5···O9vi 0.93 2.51 3.203 (4) 131
C8—H8A···O2i 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···O3i 0.93 2.54 3.178 (4) 126
C30—H30···O10 0.93 2.30 2.874 (4) 120
