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The title compound, C11H12N2O5, was prepared by the reaction of 3-amino-5-nitro­benzyl alcohol with acetic anhydride. The asymmetric unit contains three independent mol­ecules which differ in geometry only by their rotation about the single bonds external to the benzene ring. The title compound is an inter­mediate in the synthesis of DNA minor-groove-binding polybenzamide agents.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704278X/pk2042sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680704278X/pk2042Isup2.hkl
Contains datablock I

CCDC reference: 663709

Key indicators

  • Single-crystal X-ray study
  • T = 89 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.110
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.846 0.979 Tmin(prime) and Tmax expected: 0.950 0.974 RR(prime) = 0.886 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88 PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 20 Ang. PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 20 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 15
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The naturally occurring antibiotic oligopeptides distamycin A, isolated from Streptomyces Distallicus, and netropsin, from Streptomyces netropsis, are powerful DNA minor groove-binding agents but their cytotoxity precludes their use as medicines (Arcamone et al.,1964, Baraldi et al., 2004, Wemmer, 2000, Storl et al., 1993). In order to increase the DNA binding affinity and sequence specifity along with minimizing the unwanted physiological activities associated with these natural DNA binders, many synthetic oligopeptides have been prepared (Baraldi et al., 2007). The title compound is a key intermediate required in the synthesis of a novel polybenzamide DNA minor groove-binding agent. For background information on polybenzamide DNA binding agents see (Atwell et al., 1995, Turner et al., 1999, Yan et al., 1997).

Related literature top

For related literature on the biological activity of polybenzamide DNA binding agents, see: Storl et al. (1993). For related literature on natural and synthetic minor groove binding agents, see: Arcamone et al. (1964); Atwell et al. (1995); Baraldi et al. (1999, 2004, 2007); Turner et al. (1999); Wemmer (2000); Yan et al. (1997).

Experimental top

To a solution of 3-amino-5-nitrobenzyl alcohol (1 g, 5.95 mmol) in DMF (25 ml) was added acetic anhydride (1.69 ml, 17.84 mmol) and triethylamine (3.34 ml, 23.79 mmol), and the resulting mixture was stirred at room temperature for 24 h. Water (75 ml) was added, and the mixture stirred for 10 minutes. The resultant precipitate was filtered, and dried in vacuo, to afford a yellow solid, which was recrystallized from ethyl acetate to give the title compound (1.34 g, 90%), as yellow crystals suitable for X-ray crystallography (m.p. 430–431 K). Spectroscopic analysis. IR (νmax, thin film, cm-1) 3367, 1742, 1547, 1242. 1H NMR (400 MHz, CDCl3, δ, p.p.m.) 2.15 (3H, s, OCOCH3), 2.19 (3H, s, NHCOCH3, 5.15 (2H, s, CH2OAc), 7.89 (1H, s, Ar—H), 8.15 (1H, s, Ar—H), 8.34 (1H, s, Ar—H) and 9.44 (NH). 13C NMR (100 MHz, CDCl3, δ, p.p.m.) 20.8 (CH3, OCOCH3), 24.3 (CH3, NHCOCH3), 64.9 (CH2, CH2OAc), 113.7 (CH, Ar—C) 117.1 (CH, Ar—C), 124.4 (CH, Ar—C), 138.4 (quat. Ar—C), 140.2 (quat. Ar—C), 148.4 (quat. Ar—C), 169.4 (C=O, NHAc) and 170.5 (C=O, OAc). MS m/z (EI) 252 (M+, 12%), 210 (M+—C2H2O, 33), 168 (M+—C4H4O2, 52), 43 (COCH3, 100). HRMS (EI), found: M+ 252.07469. C11H12N2O5 requires: 252.07462.

Refinement top

Hydrogen atoms were placed in calculated positions and refined using the riding model [C—H 0.93–0.97, N—H 0.86 Å), with Uiso(H) = 1.2 or 1.5 times Ueq(Cmethyl).

Structure description top

The naturally occurring antibiotic oligopeptides distamycin A, isolated from Streptomyces Distallicus, and netropsin, from Streptomyces netropsis, are powerful DNA minor groove-binding agents but their cytotoxity precludes their use as medicines (Arcamone et al.,1964, Baraldi et al., 2004, Wemmer, 2000, Storl et al., 1993). In order to increase the DNA binding affinity and sequence specifity along with minimizing the unwanted physiological activities associated with these natural DNA binders, many synthetic oligopeptides have been prepared (Baraldi et al., 2007). The title compound is a key intermediate required in the synthesis of a novel polybenzamide DNA minor groove-binding agent. For background information on polybenzamide DNA binding agents see (Atwell et al., 1995, Turner et al., 1999, Yan et al., 1997).

For related literature on the biological activity of polybenzamide DNA binding agents, see: Storl et al. (1993). For related literature on natural and synthetic minor groove binding agents, see: Arcamone et al. (1964); Atwell et al. (1995); Baraldi et al. (1999, 2004, 2007); Turner et al. (1999); Wemmer (2000); Yan et al. (1997).

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1995).

Figures top
[Figure 1] Fig. 1. Structure of molecule A showing 50% probability displacement ellipsoids for non-hydrogen atoms and hydrogen atoms as arbitary spheres (Burnett & Johnson, 1996).
3-Acetamido-5-nitrobenzyl acetate top
Crystal data top
C11H12N2O5F(000) = 1584
Mr = 252.23Dx = 1.497 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5612 reflections
a = 10.5303 (2) Åθ = 1.9–26.3°
b = 21.2894 (2) ŵ = 0.12 mm1
c = 15.5410 (2) ÅT = 89 K
β = 105.508 (1)°Triangular plate, yellow
V = 3357.20 (8) Å30.42 × 0.28 × 0.22 mm
Z = 12
Data collection top
Siemens SMART CCD
diffractometer
6805 independent reflections
Radiation source: fine-focus sealed tube5399 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Area detector ω scansθmax = 26.3°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 1312
Tmin = 0.846, Tmax = 0.979k = 026
19573 measured reflectionsl = 019
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0494P)2 + 1.614P]
where P = (Fo2 + 2Fc2)/3
6805 reflections(Δ/σ)max = 0.006
493 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C11H12N2O5V = 3357.20 (8) Å3
Mr = 252.23Z = 12
Monoclinic, P21/nMo Kα radiation
a = 10.5303 (2) ŵ = 0.12 mm1
b = 21.2894 (2) ÅT = 89 K
c = 15.5410 (2) Å0.42 × 0.28 × 0.22 mm
β = 105.508 (1)°
Data collection top
Siemens SMART CCD
diffractometer
6805 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
5399 reflections with I > 2σ(I)
Tmin = 0.846, Tmax = 0.979Rint = 0.019
19573 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 1.04Δρmax = 0.32 e Å3
6805 reflectionsΔρmin = 0.35 e Å3
493 parameters
Special details top

Experimental. After primary data collection, a portion of the first block of data was re-measured to check for crystal decay. No decay was detected.

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 > 2σ(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
xyzUiso*/Ueq
O1A0.20242 (12)0.40432 (5)1.03528 (7)0.0256 (3)
O2A0.03071 (11)0.27053 (5)0.82048 (7)0.0229 (3)
O3A0.02592 (11)0.16851 (5)0.81733 (7)0.0232 (3)
O4A0.38742 (10)0.10197 (5)1.20058 (7)0.0195 (2)
O5A0.37340 (11)0.00115 (5)1.22967 (8)0.0251 (3)
N1A0.31059 (12)0.32713 (6)1.12891 (8)0.0167 (3)
H1A0.36800.32101.17910.020*
N2A0.06020 (12)0.21898 (6)0.85658 (8)0.0175 (3)
C1A0.24095 (14)0.15840 (7)1.08144 (10)0.0167 (3)
C2A0.28688 (14)0.21476 (7)1.12436 (10)0.0160 (3)
H2A0.33760.21401.18340.019*
C3A0.25812 (14)0.27261 (7)1.08026 (10)0.0153 (3)
C4A0.18188 (14)0.27437 (7)0.99157 (10)0.0161 (3)
H4A0.16060.31220.96110.019*
C5A0.13906 (14)0.21703 (7)0.95063 (10)0.0159 (3)
C6A0.16598 (14)0.15904 (7)0.99234 (10)0.0174 (3)
H6A0.13530.12200.96220.021*
C7A0.26692 (15)0.09636 (7)1.13020 (10)0.0209 (3)
H7A10.19440.08601.15520.025*
H7A20.27520.06321.08920.025*
C8A0.42784 (15)0.04897 (7)1.24824 (10)0.0189 (3)
C9A0.54698 (16)0.06175 (8)1.32327 (11)0.0256 (4)
H9A10.57250.02411.35750.038*
H9A20.52730.09401.36090.038*
H9A30.61780.07531.29970.038*
C10A0.28073 (15)0.38884 (7)1.10552 (10)0.0174 (3)
C11A0.35432 (16)0.43580 (7)1.17357 (10)0.0201 (3)
H11A0.44410.43841.17070.030*
H11B0.35230.42251.23220.030*
H11C0.31330.47631.16110.030*
O1B0.57431 (11)0.40304 (5)1.05607 (7)0.0213 (2)
O2B0.77968 (11)0.27015 (5)1.26096 (7)0.0213 (2)
O3B0.78042 (11)0.16832 (5)1.26736 (7)0.0223 (3)
O4B0.40024 (11)0.10339 (5)0.88349 (7)0.0215 (3)
O5B0.37726 (11)0.00115 (5)0.86389 (7)0.0246 (3)
N1B0.47811 (12)0.32491 (6)0.95923 (8)0.0153 (3)
H1B0.42690.31840.90680.018*
N2B0.74344 (12)0.21833 (6)1.22784 (8)0.0164 (3)
C1B0.52801 (14)0.15630 (7)1.01409 (10)0.0152 (3)
C2B0.48614 (14)0.21223 (7)0.96936 (10)0.0144 (3)
H2B0.42980.21100.91200.017*
C3B0.52750 (14)0.27076 (7)1.00929 (10)0.0135 (3)
C4B0.61325 (14)0.27305 (7)1.09487 (10)0.0148 (3)
H4B0.64270.31111.12250.018*
C5B0.65302 (14)0.21562 (7)1.13730 (9)0.0146 (3)
C6B0.61306 (14)0.15735 (7)1.10019 (10)0.0151 (3)
H6B0.64170.12041.13130.018*
C7B0.48392 (15)0.09296 (7)0.97218 (10)0.0178 (3)
H7B10.55990.06810.96940.021*
H7B20.43600.07041.00770.021*
C8B0.35221 (15)0.05156 (7)0.83557 (10)0.0182 (3)
C9B0.26650 (17)0.06949 (8)0.74595 (11)0.0265 (4)
H9B10.23110.03230.71340.040*
H9B20.31770.09220.71360.040*
H9B30.19560.09550.75320.040*
C10B0.50159 (14)0.38687 (7)0.98385 (10)0.0155 (3)
C11B0.43046 (16)0.43349 (7)0.91460 (10)0.0212 (3)
H11D0.44900.47530.93750.032*
H11E0.33730.42590.90070.032*
H11F0.45980.42890.86150.032*
O1C0.71916 (12)0.40226 (5)0.85142 (7)0.0252 (3)
O2C0.48246 (11)0.27074 (5)0.65827 (7)0.0223 (3)
O3C0.48780 (11)0.16908 (5)0.64814 (7)0.0251 (3)
O4C0.86545 (11)0.09864 (5)1.02619 (7)0.0200 (2)
O5C0.87540 (15)0.00643 (6)1.04009 (8)0.0389 (3)
N1C0.81090 (12)0.32433 (6)0.95011 (8)0.0168 (3)
H1C0.86170.31801.00270.020*
N2C0.52430 (12)0.21883 (6)0.68831 (8)0.0176 (3)
C1C0.76316 (14)0.15560 (7)0.89269 (10)0.0156 (3)
C2C0.80760 (14)0.21158 (7)0.93740 (10)0.0152 (3)
H2C0.86940.21010.99270.018*
C3C0.76084 (14)0.27013 (7)0.90059 (10)0.0149 (3)
C4C0.66657 (14)0.27263 (7)0.81786 (10)0.0160 (3)
H4C0.63390.31080.79200.019*
C5C0.62360 (14)0.21569 (7)0.77576 (10)0.0154 (3)
C6C0.66830 (14)0.15707 (7)0.81015 (10)0.0156 (3)
H6C0.63650.12030.77960.019*
C7C0.81812 (16)0.09256 (7)0.93031 (10)0.0185 (3)
H7C10.74990.06070.91500.022*
H7C20.88970.08020.90550.022*
C8C0.89136 (15)0.04494 (7)1.07379 (11)0.0186 (3)
C9C0.93755 (16)0.05777 (8)1.17183 (10)0.0222 (3)
H9C10.86570.05211.19820.033*
H9C20.96920.10021.18130.033*
H9C31.00750.02931.19890.033*
C10C0.78867 (15)0.38631 (7)0.92479 (10)0.0175 (3)
C11C0.85702 (16)0.43276 (7)0.99532 (11)0.0216 (3)
H11G0.84710.47430.97050.032*
H11H0.94900.42251.01560.032*
H11I0.81850.43101.04470.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0318 (6)0.0168 (6)0.0220 (6)0.0032 (5)0.0036 (5)0.0006 (5)
O2A0.0258 (6)0.0205 (6)0.0187 (6)0.0017 (5)0.0006 (5)0.0038 (5)
O3A0.0266 (6)0.0209 (6)0.0196 (6)0.0049 (5)0.0015 (5)0.0050 (5)
O4A0.0205 (5)0.0151 (5)0.0190 (6)0.0015 (4)0.0015 (4)0.0024 (4)
O5A0.0314 (6)0.0150 (6)0.0262 (6)0.0032 (5)0.0030 (5)0.0013 (5)
N1A0.0180 (6)0.0154 (6)0.0141 (6)0.0010 (5)0.0002 (5)0.0011 (5)
N2A0.0165 (6)0.0194 (7)0.0161 (6)0.0010 (5)0.0036 (5)0.0000 (5)
C1A0.0145 (7)0.0165 (8)0.0192 (8)0.0001 (6)0.0046 (6)0.0015 (6)
C2A0.0154 (7)0.0185 (8)0.0129 (7)0.0004 (6)0.0017 (6)0.0007 (6)
C3A0.0138 (7)0.0139 (7)0.0182 (7)0.0001 (6)0.0044 (6)0.0012 (6)
C4A0.0159 (7)0.0163 (8)0.0159 (7)0.0011 (6)0.0037 (6)0.0004 (6)
C5A0.0145 (7)0.0179 (8)0.0144 (7)0.0003 (6)0.0023 (6)0.0006 (6)
C6A0.0163 (7)0.0156 (8)0.0194 (8)0.0015 (6)0.0035 (6)0.0015 (6)
C7A0.0210 (8)0.0166 (8)0.0213 (8)0.0037 (6)0.0011 (6)0.0021 (6)
C8A0.0223 (8)0.0163 (8)0.0189 (8)0.0013 (6)0.0071 (6)0.0014 (6)
C9A0.0287 (9)0.0210 (8)0.0231 (8)0.0018 (7)0.0002 (7)0.0047 (7)
C10A0.0191 (7)0.0158 (7)0.0179 (7)0.0018 (6)0.0059 (6)0.0004 (6)
C11A0.0239 (8)0.0151 (8)0.0203 (8)0.0008 (6)0.0044 (6)0.0000 (6)
O1B0.0267 (6)0.0151 (5)0.0176 (6)0.0004 (5)0.0020 (5)0.0014 (4)
O2B0.0263 (6)0.0157 (6)0.0178 (6)0.0016 (5)0.0014 (5)0.0030 (4)
O3B0.0276 (6)0.0166 (6)0.0177 (6)0.0030 (5)0.0023 (5)0.0036 (4)
O4B0.0290 (6)0.0126 (5)0.0162 (5)0.0017 (5)0.0053 (5)0.0006 (4)
O5B0.0326 (6)0.0136 (6)0.0225 (6)0.0016 (5)0.0014 (5)0.0002 (5)
N1B0.0178 (6)0.0127 (6)0.0122 (6)0.0002 (5)0.0017 (5)0.0004 (5)
N2B0.0184 (6)0.0150 (7)0.0147 (6)0.0010 (5)0.0027 (5)0.0002 (5)
C1B0.0152 (7)0.0145 (7)0.0157 (7)0.0003 (6)0.0038 (6)0.0012 (6)
C2B0.0133 (7)0.0165 (7)0.0125 (7)0.0004 (6)0.0020 (6)0.0000 (6)
C3B0.0139 (7)0.0126 (7)0.0140 (7)0.0008 (5)0.0039 (6)0.0007 (6)
C4B0.0156 (7)0.0128 (7)0.0152 (7)0.0004 (6)0.0029 (6)0.0015 (6)
C5B0.0143 (7)0.0170 (8)0.0115 (7)0.0002 (6)0.0018 (6)0.0002 (6)
C6B0.0169 (7)0.0128 (7)0.0148 (7)0.0010 (6)0.0028 (6)0.0021 (6)
C7B0.0202 (8)0.0144 (8)0.0153 (7)0.0005 (6)0.0012 (6)0.0016 (6)
C8B0.0192 (7)0.0156 (8)0.0191 (8)0.0024 (6)0.0041 (6)0.0036 (6)
C9B0.0337 (9)0.0176 (8)0.0215 (8)0.0020 (7)0.0041 (7)0.0013 (7)
C10B0.0156 (7)0.0150 (7)0.0161 (7)0.0004 (6)0.0045 (6)0.0007 (6)
C11B0.0262 (8)0.0148 (8)0.0193 (8)0.0005 (6)0.0000 (7)0.0012 (6)
O1C0.0326 (6)0.0166 (6)0.0211 (6)0.0017 (5)0.0021 (5)0.0021 (5)
O2C0.0235 (6)0.0194 (6)0.0204 (6)0.0034 (5)0.0006 (5)0.0036 (5)
O3C0.0288 (6)0.0198 (6)0.0213 (6)0.0012 (5)0.0029 (5)0.0052 (5)
O4C0.0281 (6)0.0138 (5)0.0148 (5)0.0006 (4)0.0003 (5)0.0004 (4)
O5C0.0691 (10)0.0154 (6)0.0245 (7)0.0014 (6)0.0007 (7)0.0011 (5)
N1C0.0180 (6)0.0152 (6)0.0141 (6)0.0000 (5)0.0010 (5)0.0007 (5)
N2C0.0171 (6)0.0192 (7)0.0155 (6)0.0006 (5)0.0028 (5)0.0012 (5)
C1C0.0168 (7)0.0153 (7)0.0156 (7)0.0008 (6)0.0059 (6)0.0008 (6)
C2C0.0135 (7)0.0177 (8)0.0130 (7)0.0005 (6)0.0010 (6)0.0007 (6)
C3C0.0159 (7)0.0145 (7)0.0152 (7)0.0005 (6)0.0057 (6)0.0006 (6)
C4C0.0175 (7)0.0150 (7)0.0156 (7)0.0002 (6)0.0044 (6)0.0010 (6)
C5C0.0150 (7)0.0173 (8)0.0136 (7)0.0004 (6)0.0033 (6)0.0001 (6)
C6C0.0172 (7)0.0150 (7)0.0152 (7)0.0017 (6)0.0052 (6)0.0018 (6)
C7C0.0232 (8)0.0152 (8)0.0150 (7)0.0007 (6)0.0011 (6)0.0015 (6)
C8C0.0207 (8)0.0131 (8)0.0209 (8)0.0013 (6)0.0037 (6)0.0029 (6)
C9C0.0245 (8)0.0199 (8)0.0204 (8)0.0001 (7)0.0029 (7)0.0024 (6)
C10C0.0167 (7)0.0153 (8)0.0200 (8)0.0012 (6)0.0042 (6)0.0009 (6)
C11C0.0250 (8)0.0136 (8)0.0232 (8)0.0017 (6)0.0013 (7)0.0002 (6)
Geometric parameters (Å, º) top
O1A—C10A1.2243 (19)C3B—C4B1.394 (2)
O2A—N2A1.2339 (17)C4B—C5B1.399 (2)
O3A—N2A1.2405 (17)C4B—H4B0.9300
O4A—C8A1.3546 (18)C5B—C6B1.385 (2)
O4A—C7A1.4417 (18)C6B—H6B0.9300
O5A—C8A1.2091 (19)C7B—H7B10.9700
N1A—C10A1.377 (2)C7B—H7B20.9700
N1A—C3A1.4145 (19)C8B—C9B1.493 (2)
N1A—H1A0.8600C9B—H9B10.9600
N2A—C5A1.4761 (19)C9B—H9B20.9600
C1A—C2A1.395 (2)C9B—H9B30.9600
C1A—C6A1.399 (2)C10B—C11B1.508 (2)
C1A—C7A1.511 (2)C11B—H11D0.9600
C2A—C3A1.403 (2)C11B—H11E0.9600
C2A—H2A0.9300C11B—H11F0.9600
C3A—C4A1.398 (2)O1C—C10C1.2267 (18)
C4A—C5A1.395 (2)O2C—N2C1.2344 (17)
C4A—H4A0.9300O3C—N2C1.2372 (17)
C5A—C6A1.388 (2)O4C—C8C1.3493 (18)
C6A—H6A0.9300O4C—C7C1.4451 (17)
C7A—H7A10.9700O5C—C8C1.205 (2)
C7A—H7A20.9700N1C—C10C1.379 (2)
C8A—C9A1.492 (2)N1C—C3C1.4088 (19)
C9A—H9A10.9600N1C—H1C0.8600
C9A—H9A20.9600N2C—C5C1.4781 (19)
C9A—H9A30.9600C1C—C2C1.396 (2)
C10A—C11A1.510 (2)C1C—C6C1.400 (2)
C11A—H11A0.9600C1C—C7C1.516 (2)
C11A—H11B0.9600C2C—C3C1.404 (2)
C11A—H11C0.9600C2C—H2C0.9300
O1B—C10B1.2268 (18)C3C—C4C1.400 (2)
O2B—N2B1.2339 (16)C4C—C5C1.394 (2)
O3B—N2B1.2388 (16)C4C—H4C0.9300
O4B—C8B1.3515 (18)C5C—C6C1.389 (2)
O4B—C7B1.4409 (17)C6C—H6C0.9300
O5B—C8B1.2085 (19)C7C—H7C10.9700
N1B—C10B1.3773 (19)C7C—H7C20.9700
N1B—C3B1.4101 (19)C8C—C9C1.495 (2)
N1B—H1B0.8600C9C—H9C10.9600
N2B—C5B1.4743 (18)C9C—H9C20.9600
C1B—C2B1.390 (2)C9C—H9C30.9600
C1B—C6B1.397 (2)C10C—C11C1.509 (2)
C1B—C7B1.515 (2)C11C—H11G0.9600
C2B—C3B1.408 (2)C11C—H11H0.9600
C2B—H2B0.9300C11C—H11I0.9600
C8A—O4A—C7A115.47 (12)O4B—C7B—C1B108.23 (12)
C10A—N1A—C3A127.79 (13)O4B—C7B—H7B1110.1
C10A—N1A—H1A116.1C1B—C7B—H7B1110.1
C3A—N1A—H1A116.1O4B—C7B—H7B2110.1
O2A—N2A—O3A122.82 (13)C1B—C7B—H7B2110.1
O2A—N2A—C5A118.81 (12)H7B1—C7B—H7B2108.4
O3A—N2A—C5A118.37 (12)O5B—C8B—O4B122.98 (14)
C2A—C1A—C6A119.79 (14)O5B—C8B—C9B126.58 (14)
C2A—C1A—C7A121.27 (13)O4B—C8B—C9B110.44 (13)
C6A—C1A—C7A118.92 (13)C8B—C9B—H9B1109.5
C1A—C2A—C3A121.31 (14)C8B—C9B—H9B2109.5
C1A—C2A—H2A119.3H9B1—C9B—H9B2109.5
C3A—C2A—H2A119.3C8B—C9B—H9B3109.5
C4A—C3A—C2A119.82 (14)H9B1—C9B—H9B3109.5
C4A—C3A—N1A122.98 (13)H9B2—C9B—H9B3109.5
C2A—C3A—N1A117.19 (13)O1B—C10B—N1B123.01 (14)
C5A—C4A—C3A117.18 (14)O1B—C10B—C11B122.52 (14)
C5A—C4A—H4A121.4N1B—C10B—C11B114.47 (13)
C3A—C4A—H4A121.4C10B—C11B—H11D109.5
C6A—C5A—C4A124.39 (14)C10B—C11B—H11E109.5
C6A—C5A—N2A118.56 (13)H11D—C11B—H11E109.5
C4A—C5A—N2A117.05 (13)C10B—C11B—H11F109.5
C5A—C6A—C1A117.50 (14)H11D—C11B—H11F109.5
C5A—C6A—H6A121.3H11E—C11B—H11F109.5
C1A—C6A—H6A121.3C8C—O4C—C7C116.93 (12)
O4A—C7A—C1A108.22 (12)C10C—N1C—C3C128.15 (13)
O4A—C7A—H7A1110.1C10C—N1C—H1C115.9
C1A—C7A—H7A1110.1C3C—N1C—H1C115.9
O4A—C7A—H7A2110.1O2C—N2C—O3C122.98 (13)
C1A—C7A—H7A2110.1O2C—N2C—C5C118.77 (12)
H7A1—C7A—H7A2108.4O3C—N2C—C5C118.24 (12)
O5A—C8A—O4A123.03 (14)C2C—C1C—C6C119.95 (14)
O5A—C8A—C9A126.41 (15)C2C—C1C—C7C121.43 (13)
O4A—C8A—C9A110.56 (13)C6C—C1C—C7C118.60 (13)
C8A—C9A—H9A1109.5C1C—C2C—C3C121.37 (13)
C8A—C9A—H9A2109.5C1C—C2C—H2C119.3
H9A1—C9A—H9A2109.5C3C—C2C—H2C119.3
C8A—C9A—H9A3109.5C4C—C3C—C2C119.56 (14)
H9A1—C9A—H9A3109.5C4C—C3C—N1C122.72 (13)
H9A2—C9A—H9A3109.5C2C—C3C—N1C117.72 (13)
O1A—C10A—N1A122.96 (14)C5C—C4C—C3C117.36 (14)
O1A—C10A—C11A122.92 (14)C5C—C4C—H4C121.3
N1A—C10A—C11A114.11 (13)C3C—C4C—H4C121.3
C10A—C11A—H11A109.5C6C—C5C—C4C124.50 (14)
C10A—C11A—H11B109.5C6C—C5C—N2C118.54 (13)
H11A—C11A—H11B109.5C4C—C5C—N2C116.96 (13)
C10A—C11A—H11C109.5C5C—C6C—C1C117.26 (14)
H11A—C11A—H11C109.5C5C—C6C—H6C121.4
H11B—C11A—H11C109.5C1C—C6C—H6C121.4
C8B—O4B—C7B116.39 (12)O4C—C7C—C1C108.01 (12)
C10B—N1B—C3B128.13 (12)O4C—C7C—H7C1110.1
C10B—N1B—H1B115.9C1C—C7C—H7C1110.1
C3B—N1B—H1B115.9O4C—C7C—H7C2110.1
O2B—N2B—O3B122.71 (12)C1C—C7C—H7C2110.1
O2B—N2B—C5B118.81 (12)H7C1—C7C—H7C2108.4
O3B—N2B—C5B118.48 (12)O5C—C8C—O4C123.12 (15)
C2B—C1B—C6B120.10 (13)O5C—C8C—C9C125.33 (15)
C2B—C1B—C7B121.85 (13)O4C—C8C—C9C111.52 (13)
C6B—C1B—C7B118.05 (13)C8C—C9C—H9C1109.5
C1B—C2B—C3B121.22 (13)C8C—C9C—H9C2109.5
C1B—C2B—H2B119.4H9C1—C9C—H9C2109.5
C3B—C2B—H2B119.4C8C—C9C—H9C3109.5
C4B—C3B—C2B119.77 (13)H9C1—C9C—H9C3109.5
C4B—C3B—N1B123.15 (13)H9C2—C9C—H9C3109.5
C2B—C3B—N1B117.08 (12)O1C—C10C—N1C122.94 (14)
C3B—C4B—C5B117.05 (13)O1C—C10C—C11C122.96 (14)
C3B—C4B—H4B121.5N1C—C10C—C11C114.10 (13)
C5B—C4B—H4B121.5C10C—C11C—H11G109.5
C6B—C5B—C4B124.55 (13)C10C—C11C—H11H109.5
C6B—C5B—N2B118.63 (13)H11G—C11C—H11H109.5
C4B—C5B—N2B116.82 (13)C10C—C11C—H11I109.5
C5B—C6B—C1B117.30 (13)H11G—C11C—H11I109.5
C5B—C6B—H6B121.3H11H—C11C—H11I109.5
C1B—C6B—H6B121.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O3Ai0.862.353.1897 (17)166
N1B—H1B···O3Bii0.862.323.1506 (16)164
N1C—H1C···O3Ci0.862.313.1458 (17)164
C2A—H2A···O2Ai0.932.543.4345 (18)161
C2B—H2B···O2Bii0.932.493.4046 (18)169
C2C—H2C···O2Ci0.932.563.4546 (18)161
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC11H12N2O5
Mr252.23
Crystal system, space groupMonoclinic, P21/n
Temperature (K)89
a, b, c (Å)10.5303 (2), 21.2894 (2), 15.5410 (2)
β (°) 105.508 (1)
V3)3357.20 (8)
Z12
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.42 × 0.28 × 0.22
Data collection
DiffractometerSiemens SMART CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1997)
Tmin, Tmax0.846, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
19573, 6805, 5399
Rint0.019
(sin θ/λ)max1)0.623
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.110, 1.04
No. of reflections6805
No. of parameters493
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.35

Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXTL (Siemens, 1995).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O3Ai0.862.353.1897 (17)165.8
N1B—H1B···O3Bii0.862.323.1506 (16)163.6
N1C—H1C···O3Ci0.862.313.1458 (17)163.7
C2A—H2A···O2Ai0.932.543.4345 (18)160.7
C2B—H2B···O2Bii0.932.493.4046 (18)169.1
C2C—H2C···O2Ci0.932.563.4546 (18)160.9
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z1/2.
 

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