Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704278X/pk2042sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680704278X/pk2042Isup2.hkl |
CCDC reference: 663709
Key indicators
- Single-crystal X-ray study
- T = 89 K
- Mean (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
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).
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.
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).
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).
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).
Fig. 1. Structure of molecule A showing 50% probability displacement ellipsoids for non-hydrogen atoms and hydrogen atoms as arbitary spheres (Burnett & Johnson, 1996). |
C11H12N2O5 | F(000) = 1584 |
Mr = 252.23 | Dx = 1.497 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5612 reflections |
a = 10.5303 (2) Å | θ = 1.9–26.3° |
b = 21.2894 (2) Å | µ = 0.12 mm−1 |
c = 15.5410 (2) Å | T = 89 K |
β = 105.508 (1)° | Triangular plate, yellow |
V = 3357.20 (8) Å3 | 0.42 × 0.28 × 0.22 mm |
Z = 12 |
Siemens SMART CCD diffractometer | 6805 independent reflections |
Radiation source: fine-focus sealed tube | 5399 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
Area detector ω scans | θmax = 26.3°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −13→12 |
Tmin = 0.846, Tmax = 0.979 | k = 0→26 |
19573 measured reflections | l = 0→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-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 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C11H12N2O5 | V = 3357.20 (8) Å3 |
Mr = 252.23 | Z = 12 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.5303 (2) Å | µ = 0.12 mm−1 |
b = 21.2894 (2) Å | T = 89 K |
c = 15.5410 (2) Å | 0.42 × 0.28 × 0.22 mm |
β = 105.508 (1)° |
Siemens SMART CCD diffractometer | 6805 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 5399 reflections with I > 2σ(I) |
Tmin = 0.846, Tmax = 0.979 | Rint = 0.019 |
19573 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.32 e Å−3 |
6805 reflections | Δρmin = −0.35 e Å−3 |
493 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1A | 0.20242 (12) | 0.40432 (5) | 1.03528 (7) | 0.0256 (3) | |
O2A | 0.03071 (11) | 0.27053 (5) | 0.82048 (7) | 0.0229 (3) | |
O3A | 0.02592 (11) | 0.16851 (5) | 0.81733 (7) | 0.0232 (3) | |
O4A | 0.38742 (10) | 0.10197 (5) | 1.20058 (7) | 0.0195 (2) | |
O5A | 0.37340 (11) | −0.00115 (5) | 1.22967 (8) | 0.0251 (3) | |
N1A | 0.31059 (12) | 0.32713 (6) | 1.12891 (8) | 0.0167 (3) | |
H1A | 0.3680 | 0.3210 | 1.1791 | 0.020* | |
N2A | 0.06020 (12) | 0.21898 (6) | 0.85658 (8) | 0.0175 (3) | |
C1A | 0.24095 (14) | 0.15840 (7) | 1.08144 (10) | 0.0167 (3) | |
C2A | 0.28688 (14) | 0.21476 (7) | 1.12436 (10) | 0.0160 (3) | |
H2A | 0.3376 | 0.2140 | 1.1834 | 0.019* | |
C3A | 0.25812 (14) | 0.27261 (7) | 1.08026 (10) | 0.0153 (3) | |
C4A | 0.18188 (14) | 0.27437 (7) | 0.99157 (10) | 0.0161 (3) | |
H4A | 0.1606 | 0.3122 | 0.9611 | 0.019* | |
C5A | 0.13906 (14) | 0.21703 (7) | 0.95063 (10) | 0.0159 (3) | |
C6A | 0.16598 (14) | 0.15904 (7) | 0.99234 (10) | 0.0174 (3) | |
H6A | 0.1353 | 0.1220 | 0.9622 | 0.021* | |
C7A | 0.26692 (15) | 0.09636 (7) | 1.13020 (10) | 0.0209 (3) | |
H7A1 | 0.1944 | 0.0860 | 1.1552 | 0.025* | |
H7A2 | 0.2752 | 0.0632 | 1.0892 | 0.025* | |
C8A | 0.42784 (15) | 0.04897 (7) | 1.24824 (10) | 0.0189 (3) | |
C9A | 0.54698 (16) | 0.06175 (8) | 1.32327 (11) | 0.0256 (4) | |
H9A1 | 0.5725 | 0.0241 | 1.3575 | 0.038* | |
H9A2 | 0.5273 | 0.0940 | 1.3609 | 0.038* | |
H9A3 | 0.6178 | 0.0753 | 1.2997 | 0.038* | |
C10A | 0.28073 (15) | 0.38884 (7) | 1.10552 (10) | 0.0174 (3) | |
C11A | 0.35432 (16) | 0.43580 (7) | 1.17357 (10) | 0.0201 (3) | |
H11A | 0.4441 | 0.4384 | 1.1707 | 0.030* | |
H11B | 0.3523 | 0.4225 | 1.2322 | 0.030* | |
H11C | 0.3133 | 0.4763 | 1.1611 | 0.030* | |
O1B | 0.57431 (11) | 0.40304 (5) | 1.05607 (7) | 0.0213 (2) | |
O2B | 0.77968 (11) | 0.27015 (5) | 1.26096 (7) | 0.0213 (2) | |
O3B | 0.78042 (11) | 0.16832 (5) | 1.26736 (7) | 0.0223 (3) | |
O4B | 0.40024 (11) | 0.10339 (5) | 0.88349 (7) | 0.0215 (3) | |
O5B | 0.37726 (11) | −0.00115 (5) | 0.86389 (7) | 0.0246 (3) | |
N1B | 0.47811 (12) | 0.32491 (6) | 0.95923 (8) | 0.0153 (3) | |
H1B | 0.4269 | 0.3184 | 0.9068 | 0.018* | |
N2B | 0.74344 (12) | 0.21833 (6) | 1.22784 (8) | 0.0164 (3) | |
C1B | 0.52801 (14) | 0.15630 (7) | 1.01409 (10) | 0.0152 (3) | |
C2B | 0.48614 (14) | 0.21223 (7) | 0.96936 (10) | 0.0144 (3) | |
H2B | 0.4298 | 0.2110 | 0.9120 | 0.017* | |
C3B | 0.52750 (14) | 0.27076 (7) | 1.00929 (10) | 0.0135 (3) | |
C4B | 0.61325 (14) | 0.27305 (7) | 1.09487 (10) | 0.0148 (3) | |
H4B | 0.6427 | 0.3111 | 1.1225 | 0.018* | |
C5B | 0.65302 (14) | 0.21562 (7) | 1.13730 (9) | 0.0146 (3) | |
C6B | 0.61306 (14) | 0.15735 (7) | 1.10019 (10) | 0.0151 (3) | |
H6B | 0.6417 | 0.1204 | 1.1313 | 0.018* | |
C7B | 0.48392 (15) | 0.09296 (7) | 0.97218 (10) | 0.0178 (3) | |
H7B1 | 0.5599 | 0.0681 | 0.9694 | 0.021* | |
H7B2 | 0.4360 | 0.0704 | 1.0077 | 0.021* | |
C8B | 0.35221 (15) | 0.05156 (7) | 0.83557 (10) | 0.0182 (3) | |
C9B | 0.26650 (17) | 0.06949 (8) | 0.74595 (11) | 0.0265 (4) | |
H9B1 | 0.2311 | 0.0323 | 0.7134 | 0.040* | |
H9B2 | 0.3177 | 0.0922 | 0.7136 | 0.040* | |
H9B3 | 0.1956 | 0.0955 | 0.7532 | 0.040* | |
C10B | 0.50159 (14) | 0.38687 (7) | 0.98385 (10) | 0.0155 (3) | |
C11B | 0.43046 (16) | 0.43349 (7) | 0.91460 (10) | 0.0212 (3) | |
H11D | 0.4490 | 0.4753 | 0.9375 | 0.032* | |
H11E | 0.3373 | 0.4259 | 0.9007 | 0.032* | |
H11F | 0.4598 | 0.4289 | 0.8615 | 0.032* | |
O1C | 0.71916 (12) | 0.40226 (5) | 0.85142 (7) | 0.0252 (3) | |
O2C | 0.48246 (11) | 0.27074 (5) | 0.65827 (7) | 0.0223 (3) | |
O3C | 0.48780 (11) | 0.16908 (5) | 0.64814 (7) | 0.0251 (3) | |
O4C | 0.86545 (11) | 0.09864 (5) | 1.02619 (7) | 0.0200 (2) | |
O5C | 0.87540 (15) | −0.00643 (6) | 1.04009 (8) | 0.0389 (3) | |
N1C | 0.81090 (12) | 0.32433 (6) | 0.95011 (8) | 0.0168 (3) | |
H1C | 0.8617 | 0.3180 | 1.0027 | 0.020* | |
N2C | 0.52430 (12) | 0.21883 (6) | 0.68831 (8) | 0.0176 (3) | |
C1C | 0.76316 (14) | 0.15560 (7) | 0.89269 (10) | 0.0156 (3) | |
C2C | 0.80760 (14) | 0.21158 (7) | 0.93740 (10) | 0.0152 (3) | |
H2C | 0.8694 | 0.2101 | 0.9927 | 0.018* | |
C3C | 0.76084 (14) | 0.27013 (7) | 0.90059 (10) | 0.0149 (3) | |
C4C | 0.66657 (14) | 0.27263 (7) | 0.81786 (10) | 0.0160 (3) | |
H4C | 0.6339 | 0.3108 | 0.7920 | 0.019* | |
C5C | 0.62360 (14) | 0.21569 (7) | 0.77576 (10) | 0.0154 (3) | |
C6C | 0.66830 (14) | 0.15707 (7) | 0.81015 (10) | 0.0156 (3) | |
H6C | 0.6365 | 0.1203 | 0.7796 | 0.019* | |
C7C | 0.81812 (16) | 0.09256 (7) | 0.93031 (10) | 0.0185 (3) | |
H7C1 | 0.7499 | 0.0607 | 0.9150 | 0.022* | |
H7C2 | 0.8897 | 0.0802 | 0.9055 | 0.022* | |
C8C | 0.89136 (15) | 0.04494 (7) | 1.07379 (11) | 0.0186 (3) | |
C9C | 0.93755 (16) | 0.05777 (8) | 1.17183 (10) | 0.0222 (3) | |
H9C1 | 0.8657 | 0.0521 | 1.1982 | 0.033* | |
H9C2 | 0.9692 | 0.1002 | 1.1813 | 0.033* | |
H9C3 | 1.0075 | 0.0293 | 1.1989 | 0.033* | |
C10C | 0.78867 (15) | 0.38631 (7) | 0.92479 (10) | 0.0175 (3) | |
C11C | 0.85702 (16) | 0.43276 (7) | 0.99532 (11) | 0.0216 (3) | |
H11G | 0.8471 | 0.4743 | 0.9705 | 0.032* | |
H11H | 0.9490 | 0.4225 | 1.0156 | 0.032* | |
H11I | 0.8185 | 0.4310 | 1.0447 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0318 (6) | 0.0168 (6) | 0.0220 (6) | 0.0032 (5) | −0.0036 (5) | 0.0006 (5) |
O2A | 0.0258 (6) | 0.0205 (6) | 0.0187 (6) | 0.0017 (5) | −0.0006 (5) | 0.0038 (5) |
O3A | 0.0266 (6) | 0.0209 (6) | 0.0196 (6) | −0.0049 (5) | 0.0015 (5) | −0.0050 (5) |
O4A | 0.0205 (5) | 0.0151 (5) | 0.0190 (6) | −0.0015 (4) | −0.0015 (4) | 0.0024 (4) |
O5A | 0.0314 (6) | 0.0150 (6) | 0.0262 (6) | −0.0032 (5) | 0.0030 (5) | 0.0013 (5) |
N1A | 0.0180 (6) | 0.0154 (6) | 0.0141 (6) | 0.0010 (5) | −0.0002 (5) | −0.0011 (5) |
N2A | 0.0165 (6) | 0.0194 (7) | 0.0161 (6) | −0.0010 (5) | 0.0036 (5) | 0.0000 (5) |
C1A | 0.0145 (7) | 0.0165 (8) | 0.0192 (8) | 0.0001 (6) | 0.0046 (6) | 0.0015 (6) |
C2A | 0.0154 (7) | 0.0185 (8) | 0.0129 (7) | 0.0004 (6) | 0.0017 (6) | 0.0007 (6) |
C3A | 0.0138 (7) | 0.0139 (7) | 0.0182 (7) | −0.0001 (6) | 0.0044 (6) | −0.0012 (6) |
C4A | 0.0159 (7) | 0.0163 (8) | 0.0159 (7) | 0.0011 (6) | 0.0037 (6) | 0.0004 (6) |
C5A | 0.0145 (7) | 0.0179 (8) | 0.0144 (7) | 0.0003 (6) | 0.0023 (6) | 0.0006 (6) |
C6A | 0.0163 (7) | 0.0156 (8) | 0.0194 (8) | −0.0015 (6) | 0.0035 (6) | −0.0015 (6) |
C7A | 0.0210 (8) | 0.0166 (8) | 0.0213 (8) | −0.0037 (6) | −0.0011 (6) | 0.0021 (6) |
C8A | 0.0223 (8) | 0.0163 (8) | 0.0189 (8) | 0.0013 (6) | 0.0071 (6) | 0.0014 (6) |
C9A | 0.0287 (9) | 0.0210 (8) | 0.0231 (8) | 0.0018 (7) | 0.0002 (7) | 0.0047 (7) |
C10A | 0.0191 (7) | 0.0158 (7) | 0.0179 (7) | 0.0018 (6) | 0.0059 (6) | 0.0004 (6) |
C11A | 0.0239 (8) | 0.0151 (8) | 0.0203 (8) | 0.0008 (6) | 0.0044 (6) | 0.0000 (6) |
O1B | 0.0267 (6) | 0.0151 (5) | 0.0176 (6) | −0.0004 (5) | −0.0020 (5) | −0.0014 (4) |
O2B | 0.0263 (6) | 0.0157 (6) | 0.0178 (6) | −0.0016 (5) | −0.0014 (5) | −0.0030 (4) |
O3B | 0.0276 (6) | 0.0166 (6) | 0.0177 (6) | 0.0030 (5) | −0.0023 (5) | 0.0036 (4) |
O4B | 0.0290 (6) | 0.0126 (5) | 0.0162 (5) | −0.0017 (5) | −0.0053 (5) | −0.0006 (4) |
O5B | 0.0326 (6) | 0.0136 (6) | 0.0225 (6) | −0.0016 (5) | −0.0014 (5) | 0.0002 (5) |
N1B | 0.0178 (6) | 0.0127 (6) | 0.0122 (6) | 0.0002 (5) | −0.0017 (5) | 0.0004 (5) |
N2B | 0.0184 (6) | 0.0150 (7) | 0.0147 (6) | 0.0010 (5) | 0.0027 (5) | 0.0002 (5) |
C1B | 0.0152 (7) | 0.0145 (7) | 0.0157 (7) | 0.0003 (6) | 0.0038 (6) | −0.0012 (6) |
C2B | 0.0133 (7) | 0.0165 (7) | 0.0125 (7) | −0.0004 (6) | 0.0020 (6) | 0.0000 (6) |
C3B | 0.0139 (7) | 0.0126 (7) | 0.0140 (7) | 0.0008 (5) | 0.0039 (6) | 0.0007 (6) |
C4B | 0.0156 (7) | 0.0128 (7) | 0.0152 (7) | −0.0004 (6) | 0.0029 (6) | −0.0015 (6) |
C5B | 0.0143 (7) | 0.0170 (8) | 0.0115 (7) | 0.0002 (6) | 0.0018 (6) | 0.0002 (6) |
C6B | 0.0169 (7) | 0.0128 (7) | 0.0148 (7) | 0.0010 (6) | 0.0028 (6) | 0.0021 (6) |
C7B | 0.0202 (8) | 0.0144 (8) | 0.0153 (7) | 0.0005 (6) | −0.0012 (6) | 0.0016 (6) |
C8B | 0.0192 (7) | 0.0156 (8) | 0.0191 (8) | −0.0024 (6) | 0.0041 (6) | −0.0036 (6) |
C9B | 0.0337 (9) | 0.0176 (8) | 0.0215 (8) | −0.0020 (7) | −0.0041 (7) | −0.0013 (7) |
C10B | 0.0156 (7) | 0.0150 (7) | 0.0161 (7) | 0.0004 (6) | 0.0045 (6) | 0.0007 (6) |
C11B | 0.0262 (8) | 0.0148 (8) | 0.0193 (8) | 0.0005 (6) | 0.0000 (7) | 0.0012 (6) |
O1C | 0.0326 (6) | 0.0166 (6) | 0.0211 (6) | −0.0017 (5) | −0.0021 (5) | 0.0021 (5) |
O2C | 0.0235 (6) | 0.0194 (6) | 0.0204 (6) | 0.0034 (5) | −0.0006 (5) | 0.0036 (5) |
O3C | 0.0288 (6) | 0.0198 (6) | 0.0213 (6) | −0.0012 (5) | −0.0029 (5) | −0.0052 (5) |
O4C | 0.0281 (6) | 0.0138 (5) | 0.0148 (5) | 0.0006 (4) | −0.0003 (5) | 0.0004 (4) |
O5C | 0.0691 (10) | 0.0154 (6) | 0.0245 (7) | 0.0014 (6) | −0.0007 (7) | 0.0011 (5) |
N1C | 0.0180 (6) | 0.0152 (6) | 0.0141 (6) | 0.0000 (5) | −0.0010 (5) | −0.0007 (5) |
N2C | 0.0171 (6) | 0.0192 (7) | 0.0155 (6) | −0.0006 (5) | 0.0028 (5) | −0.0012 (5) |
C1C | 0.0168 (7) | 0.0153 (7) | 0.0156 (7) | 0.0008 (6) | 0.0059 (6) | 0.0008 (6) |
C2C | 0.0135 (7) | 0.0177 (8) | 0.0130 (7) | 0.0005 (6) | 0.0010 (6) | 0.0007 (6) |
C3C | 0.0159 (7) | 0.0145 (7) | 0.0152 (7) | −0.0005 (6) | 0.0057 (6) | −0.0006 (6) |
C4C | 0.0175 (7) | 0.0150 (7) | 0.0156 (7) | 0.0002 (6) | 0.0044 (6) | 0.0010 (6) |
C5C | 0.0150 (7) | 0.0173 (8) | 0.0136 (7) | 0.0004 (6) | 0.0033 (6) | 0.0001 (6) |
C6C | 0.0172 (7) | 0.0150 (7) | 0.0152 (7) | −0.0017 (6) | 0.0052 (6) | −0.0018 (6) |
C7C | 0.0232 (8) | 0.0152 (8) | 0.0150 (7) | 0.0007 (6) | 0.0011 (6) | −0.0015 (6) |
C8C | 0.0207 (8) | 0.0131 (8) | 0.0209 (8) | 0.0013 (6) | 0.0037 (6) | 0.0029 (6) |
C9C | 0.0245 (8) | 0.0199 (8) | 0.0204 (8) | 0.0001 (7) | 0.0029 (7) | 0.0024 (6) |
C10C | 0.0167 (7) | 0.0153 (8) | 0.0200 (8) | −0.0012 (6) | 0.0042 (6) | 0.0009 (6) |
C11C | 0.0250 (8) | 0.0136 (8) | 0.0232 (8) | −0.0017 (6) | 0.0013 (7) | 0.0002 (6) |
O1A—C10A | 1.2243 (19) | C3B—C4B | 1.394 (2) |
O2A—N2A | 1.2339 (17) | C4B—C5B | 1.399 (2) |
O3A—N2A | 1.2405 (17) | C4B—H4B | 0.9300 |
O4A—C8A | 1.3546 (18) | C5B—C6B | 1.385 (2) |
O4A—C7A | 1.4417 (18) | C6B—H6B | 0.9300 |
O5A—C8A | 1.2091 (19) | C7B—H7B1 | 0.9700 |
N1A—C10A | 1.377 (2) | C7B—H7B2 | 0.9700 |
N1A—C3A | 1.4145 (19) | C8B—C9B | 1.493 (2) |
N1A—H1A | 0.8600 | C9B—H9B1 | 0.9600 |
N2A—C5A | 1.4761 (19) | C9B—H9B2 | 0.9600 |
C1A—C2A | 1.395 (2) | C9B—H9B3 | 0.9600 |
C1A—C6A | 1.399 (2) | C10B—C11B | 1.508 (2) |
C1A—C7A | 1.511 (2) | C11B—H11D | 0.9600 |
C2A—C3A | 1.403 (2) | C11B—H11E | 0.9600 |
C2A—H2A | 0.9300 | C11B—H11F | 0.9600 |
C3A—C4A | 1.398 (2) | O1C—C10C | 1.2267 (18) |
C4A—C5A | 1.395 (2) | O2C—N2C | 1.2344 (17) |
C4A—H4A | 0.9300 | O3C—N2C | 1.2372 (17) |
C5A—C6A | 1.388 (2) | O4C—C8C | 1.3493 (18) |
C6A—H6A | 0.9300 | O4C—C7C | 1.4451 (17) |
C7A—H7A1 | 0.9700 | O5C—C8C | 1.205 (2) |
C7A—H7A2 | 0.9700 | N1C—C10C | 1.379 (2) |
C8A—C9A | 1.492 (2) | N1C—C3C | 1.4088 (19) |
C9A—H9A1 | 0.9600 | N1C—H1C | 0.8600 |
C9A—H9A2 | 0.9600 | N2C—C5C | 1.4781 (19) |
C9A—H9A3 | 0.9600 | C1C—C2C | 1.396 (2) |
C10A—C11A | 1.510 (2) | C1C—C6C | 1.400 (2) |
C11A—H11A | 0.9600 | C1C—C7C | 1.516 (2) |
C11A—H11B | 0.9600 | C2C—C3C | 1.404 (2) |
C11A—H11C | 0.9600 | C2C—H2C | 0.9300 |
O1B—C10B | 1.2268 (18) | C3C—C4C | 1.400 (2) |
O2B—N2B | 1.2339 (16) | C4C—C5C | 1.394 (2) |
O3B—N2B | 1.2388 (16) | C4C—H4C | 0.9300 |
O4B—C8B | 1.3515 (18) | C5C—C6C | 1.389 (2) |
O4B—C7B | 1.4409 (17) | C6C—H6C | 0.9300 |
O5B—C8B | 1.2085 (19) | C7C—H7C1 | 0.9700 |
N1B—C10B | 1.3773 (19) | C7C—H7C2 | 0.9700 |
N1B—C3B | 1.4101 (19) | C8C—C9C | 1.495 (2) |
N1B—H1B | 0.8600 | C9C—H9C1 | 0.9600 |
N2B—C5B | 1.4743 (18) | C9C—H9C2 | 0.9600 |
C1B—C2B | 1.390 (2) | C9C—H9C3 | 0.9600 |
C1B—C6B | 1.397 (2) | C10C—C11C | 1.509 (2) |
C1B—C7B | 1.515 (2) | C11C—H11G | 0.9600 |
C2B—C3B | 1.408 (2) | C11C—H11H | 0.9600 |
C2B—H2B | 0.9300 | C11C—H11I | 0.9600 |
C8A—O4A—C7A | 115.47 (12) | O4B—C7B—C1B | 108.23 (12) |
C10A—N1A—C3A | 127.79 (13) | O4B—C7B—H7B1 | 110.1 |
C10A—N1A—H1A | 116.1 | C1B—C7B—H7B1 | 110.1 |
C3A—N1A—H1A | 116.1 | O4B—C7B—H7B2 | 110.1 |
O2A—N2A—O3A | 122.82 (13) | C1B—C7B—H7B2 | 110.1 |
O2A—N2A—C5A | 118.81 (12) | H7B1—C7B—H7B2 | 108.4 |
O3A—N2A—C5A | 118.37 (12) | O5B—C8B—O4B | 122.98 (14) |
C2A—C1A—C6A | 119.79 (14) | O5B—C8B—C9B | 126.58 (14) |
C2A—C1A—C7A | 121.27 (13) | O4B—C8B—C9B | 110.44 (13) |
C6A—C1A—C7A | 118.92 (13) | C8B—C9B—H9B1 | 109.5 |
C1A—C2A—C3A | 121.31 (14) | C8B—C9B—H9B2 | 109.5 |
C1A—C2A—H2A | 119.3 | H9B1—C9B—H9B2 | 109.5 |
C3A—C2A—H2A | 119.3 | C8B—C9B—H9B3 | 109.5 |
C4A—C3A—C2A | 119.82 (14) | H9B1—C9B—H9B3 | 109.5 |
C4A—C3A—N1A | 122.98 (13) | H9B2—C9B—H9B3 | 109.5 |
C2A—C3A—N1A | 117.19 (13) | O1B—C10B—N1B | 123.01 (14) |
C5A—C4A—C3A | 117.18 (14) | O1B—C10B—C11B | 122.52 (14) |
C5A—C4A—H4A | 121.4 | N1B—C10B—C11B | 114.47 (13) |
C3A—C4A—H4A | 121.4 | C10B—C11B—H11D | 109.5 |
C6A—C5A—C4A | 124.39 (14) | C10B—C11B—H11E | 109.5 |
C6A—C5A—N2A | 118.56 (13) | H11D—C11B—H11E | 109.5 |
C4A—C5A—N2A | 117.05 (13) | C10B—C11B—H11F | 109.5 |
C5A—C6A—C1A | 117.50 (14) | H11D—C11B—H11F | 109.5 |
C5A—C6A—H6A | 121.3 | H11E—C11B—H11F | 109.5 |
C1A—C6A—H6A | 121.3 | C8C—O4C—C7C | 116.93 (12) |
O4A—C7A—C1A | 108.22 (12) | C10C—N1C—C3C | 128.15 (13) |
O4A—C7A—H7A1 | 110.1 | C10C—N1C—H1C | 115.9 |
C1A—C7A—H7A1 | 110.1 | C3C—N1C—H1C | 115.9 |
O4A—C7A—H7A2 | 110.1 | O2C—N2C—O3C | 122.98 (13) |
C1A—C7A—H7A2 | 110.1 | O2C—N2C—C5C | 118.77 (12) |
H7A1—C7A—H7A2 | 108.4 | O3C—N2C—C5C | 118.24 (12) |
O5A—C8A—O4A | 123.03 (14) | C2C—C1C—C6C | 119.95 (14) |
O5A—C8A—C9A | 126.41 (15) | C2C—C1C—C7C | 121.43 (13) |
O4A—C8A—C9A | 110.56 (13) | C6C—C1C—C7C | 118.60 (13) |
C8A—C9A—H9A1 | 109.5 | C1C—C2C—C3C | 121.37 (13) |
C8A—C9A—H9A2 | 109.5 | C1C—C2C—H2C | 119.3 |
H9A1—C9A—H9A2 | 109.5 | C3C—C2C—H2C | 119.3 |
C8A—C9A—H9A3 | 109.5 | C4C—C3C—C2C | 119.56 (14) |
H9A1—C9A—H9A3 | 109.5 | C4C—C3C—N1C | 122.72 (13) |
H9A2—C9A—H9A3 | 109.5 | C2C—C3C—N1C | 117.72 (13) |
O1A—C10A—N1A | 122.96 (14) | C5C—C4C—C3C | 117.36 (14) |
O1A—C10A—C11A | 122.92 (14) | C5C—C4C—H4C | 121.3 |
N1A—C10A—C11A | 114.11 (13) | C3C—C4C—H4C | 121.3 |
C10A—C11A—H11A | 109.5 | C6C—C5C—C4C | 124.50 (14) |
C10A—C11A—H11B | 109.5 | C6C—C5C—N2C | 118.54 (13) |
H11A—C11A—H11B | 109.5 | C4C—C5C—N2C | 116.96 (13) |
C10A—C11A—H11C | 109.5 | C5C—C6C—C1C | 117.26 (14) |
H11A—C11A—H11C | 109.5 | C5C—C6C—H6C | 121.4 |
H11B—C11A—H11C | 109.5 | C1C—C6C—H6C | 121.4 |
C8B—O4B—C7B | 116.39 (12) | O4C—C7C—C1C | 108.01 (12) |
C10B—N1B—C3B | 128.13 (12) | O4C—C7C—H7C1 | 110.1 |
C10B—N1B—H1B | 115.9 | C1C—C7C—H7C1 | 110.1 |
C3B—N1B—H1B | 115.9 | O4C—C7C—H7C2 | 110.1 |
O2B—N2B—O3B | 122.71 (12) | C1C—C7C—H7C2 | 110.1 |
O2B—N2B—C5B | 118.81 (12) | H7C1—C7C—H7C2 | 108.4 |
O3B—N2B—C5B | 118.48 (12) | O5C—C8C—O4C | 123.12 (15) |
C2B—C1B—C6B | 120.10 (13) | O5C—C8C—C9C | 125.33 (15) |
C2B—C1B—C7B | 121.85 (13) | O4C—C8C—C9C | 111.52 (13) |
C6B—C1B—C7B | 118.05 (13) | C8C—C9C—H9C1 | 109.5 |
C1B—C2B—C3B | 121.22 (13) | C8C—C9C—H9C2 | 109.5 |
C1B—C2B—H2B | 119.4 | H9C1—C9C—H9C2 | 109.5 |
C3B—C2B—H2B | 119.4 | C8C—C9C—H9C3 | 109.5 |
C4B—C3B—C2B | 119.77 (13) | H9C1—C9C—H9C3 | 109.5 |
C4B—C3B—N1B | 123.15 (13) | H9C2—C9C—H9C3 | 109.5 |
C2B—C3B—N1B | 117.08 (12) | O1C—C10C—N1C | 122.94 (14) |
C3B—C4B—C5B | 117.05 (13) | O1C—C10C—C11C | 122.96 (14) |
C3B—C4B—H4B | 121.5 | N1C—C10C—C11C | 114.10 (13) |
C5B—C4B—H4B | 121.5 | C10C—C11C—H11G | 109.5 |
C6B—C5B—C4B | 124.55 (13) | C10C—C11C—H11H | 109.5 |
C6B—C5B—N2B | 118.63 (13) | H11G—C11C—H11H | 109.5 |
C4B—C5B—N2B | 116.82 (13) | C10C—C11C—H11I | 109.5 |
C5B—C6B—C1B | 117.30 (13) | H11G—C11C—H11I | 109.5 |
C5B—C6B—H6B | 121.3 | H11H—C11C—H11I | 109.5 |
C1B—C6B—H6B | 121.3 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O3Ai | 0.86 | 2.35 | 3.1897 (17) | 166 |
N1B—H1B···O3Bii | 0.86 | 2.32 | 3.1506 (16) | 164 |
N1C—H1C···O3Ci | 0.86 | 2.31 | 3.1458 (17) | 164 |
C2A—H2A···O2Ai | 0.93 | 2.54 | 3.4345 (18) | 161 |
C2B—H2B···O2Bii | 0.93 | 2.49 | 3.4046 (18) | 169 |
C2C—H2C···O2Ci | 0.93 | 2.56 | 3.4546 (18) | 161 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H12N2O5 |
Mr | 252.23 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 89 |
a, b, c (Å) | 10.5303 (2), 21.2894 (2), 15.5410 (2) |
β (°) | 105.508 (1) |
V (Å3) | 3357.20 (8) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.42 × 0.28 × 0.22 |
Data collection | |
Diffractometer | Siemens SMART CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.846, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19573, 6805, 5399 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.623 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.110, 1.04 |
No. of reflections | 6805 |
No. of parameters | 493 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O3Ai | 0.86 | 2.35 | 3.1897 (17) | 165.8 |
N1B—H1B···O3Bii | 0.86 | 2.32 | 3.1506 (16) | 163.6 |
N1C—H1C···O3Ci | 0.86 | 2.31 | 3.1458 (17) | 163.7 |
C2A—H2A···O2Ai | 0.93 | 2.54 | 3.4345 (18) | 160.7 |
C2B—H2B···O2Bii | 0.93 | 2.49 | 3.4046 (18) | 169.1 |
C2C—H2C···O2Ci | 0.93 | 2.56 | 3.4546 (18) | 160.9 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2. |
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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).