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.
Supporting information
CCDC reference: 197464
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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.
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.
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).
N-[3-nitrophenyl]acetamide
top
Crystal data top
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) Å3 | Pyramidal, pale orange |
Z = 8 | 0.39 × 0.35 × 0.16 mm |
Data collection top
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 top
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) = 0.154 | w = 1/[σ2(Fo2) + (0.1044P)2 + 0.024P] where P = (Fo2 + 2Fc2)/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) |
Crystal data top
C8H8N2O3 | V = 1679.8 (6) Å3 |
Mr = 180.16 | Z = 8 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.767 (2) Å | µ = 0.11 mm−1 |
b = 13.298 (3) Å | T = 293 K |
c = 13.272 (3) Å | 0.39 × 0.35 × 0.16 mm |
β = 102.991 (5)° | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 5863 reflections with I > 2σ(I) |
14297 measured reflections | Rint = 0.026 |
6994 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.154 | Δρmax = 0.35 e Å−3 |
S = 1.07 | Δρmin = −0.45 e Å−3 |
6994 reflections | Absolute structure: (Flack, 1983), 817 Friedel pairs |
473 parameters | Absolute structure parameter: −0.01 (10) |
1 restraint | |
Special details top
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) top | 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 (Å2) top | 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) |
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) top
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···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) |
O9···C5viii | 3.203 (4) | C4···H16Aii | 3.0756 |
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 |
N3···O10xii | 2.894 (3) | H16B···H3 | 2.1917 |
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) |
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O7viii | 0.86 | 2.06 | 2.911 (3) | 169 |
N3—H3···O10xii | 0.86 | 2.03 | 2.894 (3) | 178 |
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 |
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. |
Experimental details
Crystal data |
Chemical formula | C8H8N2O3 |
Mr | 180.16 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 293 |
a, b, c (Å) | 9.767 (2), 13.298 (3), 13.272 (3) |
β (°) | 102.991 (5) |
V (Å3) | 1679.8 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.39 × 0.35 × 0.16 |
|
Data collection |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14297, 6994, 5863 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.660 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.154, 1.07 |
No. of reflections | 6994 |
No. of parameters | 473 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.45 |
Absolute structure | (Flack, 1983), 817 Friedel pairs |
Absolute structure parameter | −0.01 (10) |
Selected geometric parameters (Å, º) topO1—C7 | 1.216 (3) | N1—C1 | 1.386 (3) |
O2—N2 | 1.207 (3) | N1—C7 | 1.362 (3) |
O3—N2 | 1.204 (3) | N2—C3 | 1.476 (3) |
O4—C15 | 1.209 (3) | N3—C9 | 1.404 (3) |
O5—N4 | 1.208 (3) | N3—C15 | 1.347 (3) |
O6—N4 | 1.225 (3) | N4—C11 | 1.469 (3) |
O7—C23 | 1.225 (3) | N5—C23 | 1.345 (3) |
O8—N6 | 1.221 (3) | N5—C17 | 1.395 (3) |
O9—N6 | 1.207 (3) | N6—C19 | 1.474 (3) |
O10—C31 | 1.212 (3) | N7—C31 | 1.344 (3) |
O11—N8 | 1.214 (3) | N7—C25 | 1.405 (3) |
O12—N8 | 1.225 (4) | N8—C27 | 1.468 (4) |
| | | |
C7—N1—C1—C6 | −171.9 (2) | C17—N5—C23—C24 | 176.6 (2) |
C1—N1—C7—C8 | −179.0 (2) | O9—N6—C19—C18 | 176.4 (2) |
O2—N2—C3—C4 | 179.9 (2) | O8—N6—C19—C20 | 175.7 (2) |
O3—N2—C3—C2 | −179.8 (2) | C31—N7—C25—C26 | 172.5 (2) |
C9—N3—C15—C16 | 175.6 (3) | C25—N7—C31—C32 | −178.3 (2) |
O5—N4—C11—C12 | −179.2 (2) | O11—N8—C27—C28 | 178.7 (3) |
O6—N4—C11—C10 | −179.2 (2) | O11—N8—C27—C26 | −1.1 (4) |
C23—N5—C17—C22 | 178.3 (2) | O12—N8—C27—C26 | 178.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O7i | 0.86 | 2.06 | 2.911 (3) | 169 |
N3—H3···O10ii | 0.86 | 2.03 | 2.894 (3) | 178 |
N5—H5A···O1iii | 0.86 | 2.06 | 2.922 (3) | 178 |
N7—H7···O4iv | 0.86 | 2.06 | 2.908 (3) | 171 |
C2—H2···O1 | 0.93 | 2.29 | 2.861 (3) | 119 |
C5—H5···O9v | 0.93 | 2.51 | 3.203 (4) | 131 |
C8—H8A···O2vi | 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···O3vi | 0.93 | 2.54 | 3.178 (4) | 126 |
C30—H30···O10 | 0.93 | 2.30 | 2.874 (4) | 120 |
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) x+1, y−1, z; (iii) −x+1, y+1/2, −z+1; (iv) x, y+1, z; (v) −x, y+1/2, −z+1; (vi) −x+1, y−1/2, −z+1. |
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).