PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1122–o1123.
Published online 2009 April 25. doi:  10.1107/S1600536809014780
PMCID: PMC2977797

4-Butyl­amino-3-nitro­benzoic acid

Abstract

The asymmetric unit of the title compound, C11H14N2O4, comprises four crystallographically independent mol­ecules (A, B, C and D) with similar geometries. In each mol­ecule, the butyl­amino side chain is in an extended conformation, and the carboxyl and butyl­amino groups are almost coplanar with the attached benzene ring; the nitro group is slightly twisted away from the benzene ring. In the asymmetric unit, the benzene rings of mol­ecules A, B and C are stacked parallel to one another, with a centroid–centroid distance of 3.6197 (11) or 3.6569 (11) Å, indicating π–π inter­actions. An intra­molecular N—H(...)O hydrogen bond is observed in each independent mol­ecule. In addition to the π–π inter­actions, the crystal packing is consolidated by inter­molecular O—H(...)O and C—H(...)O hydrogen bonds and C—H(...)π inter­actions. The crystal studied was a non-merohedral twin. The minor twin component refined to a value of 0.290 (1).

Related literature

For the synthesis of nitro­benzoic acid derivatives, see: Ishida et al. (2006 [triangle]); Mohd Maidin et al. (2008 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1122-scheme1.jpg

Experimental

Crystal data

  • C11H14N2O4
  • M r = 238.24
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1122-efi1.jpg
  • a = 14.5188 (6) Å
  • b = 13.8801 (6) Å
  • c = 22.5694 (9) Å
  • β = 90.233 (2)°
  • V = 4548.2 (3) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 100 K
  • 0.52 × 0.19 × 0.13 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.946, T max = 0.986
  • 137935 measured reflections
  • 15056 independent reflections
  • 11743 reflections with I > 2σ(I)
  • R int = 0.066

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.163
  • S = 1.06
  • 15056 reflections
  • 622 parameters
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014780/ci2784sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014780/ci2784Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The synthetic chemistry work was funded by Universiti Sains Malaysia (USM) under University Research grant No. 1001/PFARMASI/815026. HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. HKF also thanks the Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. SNNB and SRJ thank Universiti Sains Malaysia for a postdoctoral research fellowship.

supplementary crystallographic information

Comment

Synthesis of biologically active heterocyclic scaffolds can be accessed conveniently via nitro benzoic acid intermediates (Ishida et al., 2006). We synthesized the title compound as an intermediate, and herein we report its crystal structure.

The asymmetric unit of of the title compound (Fig.1) comprises of four crystallographically independent molecules (A, B, C & D) with similar geometries. The bond lengths (Allen et al., 1987) and angles have normal values. In each of these molecules, the butylamino side chain is in an extended conformation. The carboxyl and butylamino groups are almost coplanar with the attached bezene ring. The nitro group is slightly twisted away from the benzene ring, with the dihedral angle between them being 13.79 (10)° in molecule A [10.39 (10)° in B, 5.88 (10)° in C and 9.52 (10)° in D]. In the asymmetric unit, molecules A, B and C are stacked almost parallel to one another but the orientation of the molecule D is different. The benzene ring of molecule A forms dihedral angles of 2.93 (9) and 1.95 (9)°, respectively, with benzene rings of molecules B and C. The benzene ring of molecule D forms dihedral angles of 49.37 (9), 47.22 (9) and 47.73 (9)°, respectively, with benzene rings of molecules A, B and C.

An intramolecular N—H···O hydrogen bond is observed in each independent molecule. In the asymmetric unit, molecules B and D are linked via a C—H···O hydrogen bond. The crystal packing (Fig. 2) is consolidated by intermolecular O—H···O and C—H···O hydrogen bonds and intermolecular C—H···π interactions (Table 1). In addition, π-π interactions are observed between the benzene rings of molecules A, B and C, with Cg1···Cg2 and Cg2···Cg3 distances of 3.6197 (11) Å and 3.6569 (11) Å, respectively; Cg1, Cg2 and Cg3 are centroids of the C1A-C6A, C1B-C6B and C1C-C6B benzene rings, respectively.

Experimental

A mixture of ethyl 4-butylamino-3-nitro-benzoate (0.5 g, 0.0018 mol) (Mohd Maidin et al., 2008) and KOH (0.10 g, 0.0018 mol) was refluxed in aqueous ethanol (10 ml) for 3 h. After completion of the reaction, ethanol was distilled off and the reaction mixture was diluted with water (15 ml). The aqueous layer was washed with dichloromethane (5 × 2 ml) and acidified with concentrated hydrochloric acid to afford yellow precipitate as the crude product. Recrystallization of the crude product with hot ethyl acetate gave the title compound as yellow needles.

Refinement

H atoms were positioned geometrically [C-H = 0.96–0.97 Å; O-H = 0.82 Å and N-H = 0.86 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(O,Cmethyl). A rotating–group model was used for the methyl groups. The crystal studied was a non-merohedral twin. The minor twin component refined to a value of 0.290 (1).

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
The crystal packing of the title compound, viewed along the a axis. Dashed lines indicate the hydrogen bonding.

Crystal data

C11H14N2O4F(000) = 2016
Mr = 238.24Dx = 1.392 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9852 reflections
a = 14.5188 (6) Åθ = 2.2–31.6°
b = 13.8801 (6) ŵ = 0.11 mm1
c = 22.5694 (9) ÅT = 100 K
β = 90.233 (2)°Needle, yellow
V = 4548.2 (3) Å30.52 × 0.19 × 0.13 mm
Z = 16

Data collection

Bruker SMART APEXII CCD area-detector diffractometer15056 independent reflections
Radiation source: fine-focus sealed tube11743 reflections with I > 2σ(I)
graphiteRint = 0.066
[var phi] and ω scansθmax = 31.5°, θmin = 0.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −21→20
Tmin = 0.946, Tmax = 0.986k = −20→20
137935 measured reflectionsl = −33→33

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0774P)2 + 1.2697P] where P = (Fo2 + 2Fc2)/3
15056 reflections(Δ/σ)max = 0.001
622 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = −0.23 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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 > 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)

xyzUiso*/Ueq
O1A0.47049 (11)0.07879 (11)0.44554 (7)0.0282 (3)
O2A0.54315 (11)−0.06355 (10)0.43941 (7)0.0279 (3)
H2A0.5392−0.06010.47560.042*
O3A0.63546 (10)−0.18919 (10)0.25553 (7)0.0274 (3)
O4A0.57916 (12)−0.13846 (11)0.17198 (7)0.0311 (3)
N1A0.59022 (11)−0.13029 (11)0.22614 (8)0.0224 (3)
N2A0.50963 (11)0.03823 (11)0.16551 (8)0.0209 (3)
H2AB0.5247−0.01190.14530.025*
C1A0.48194 (13)0.10971 (13)0.26041 (9)0.0205 (4)
H1AA0.46170.16600.24210.025*
C2A0.48021 (13)0.10388 (13)0.32115 (9)0.0200 (4)
H2AA0.45720.15520.34300.024*
C3A0.51283 (13)0.02098 (13)0.35082 (9)0.0195 (4)
C4A0.54881 (12)−0.05358 (13)0.31793 (9)0.0200 (4)
H4AA0.5726−0.10760.33700.024*
C5A0.54979 (13)−0.04862 (13)0.25652 (9)0.0194 (4)
C6A0.51375 (12)0.03214 (13)0.22463 (9)0.0192 (4)
C7A0.48124 (14)0.12411 (13)0.13296 (9)0.0213 (4)
H7AA0.52190.17720.14270.026*
H7AB0.41920.14190.14430.026*
C8A0.48435 (14)0.10498 (14)0.06642 (9)0.0216 (4)
H8AA0.54610.08540.05550.026*
H8AB0.44280.05240.05690.026*
C9A0.45733 (17)0.19300 (14)0.03070 (10)0.0282 (4)
H9AA0.50010.24490.03930.034*
H9AB0.39640.21390.04270.034*
C10A0.45701 (18)0.17360 (16)−0.03620 (10)0.0314 (5)
H10A0.43930.2311−0.05690.047*
H10B0.41400.1230−0.04510.047*
H10C0.51760.1545−0.04850.047*
C11A0.50779 (13)0.01307 (13)0.41582 (9)0.0208 (4)
O1B0.23328 (11)0.07949 (10)0.09745 (7)0.0287 (3)
O2B0.29894 (11)−0.06670 (10)0.10319 (7)0.0273 (3)
H2B0.2955−0.06260.06700.041*
O3B0.37906 (10)−0.20336 (9)0.28766 (7)0.0255 (3)
O4B0.33005 (12)−0.14787 (11)0.37108 (7)0.0330 (4)
N1B0.33887 (11)−0.14104 (11)0.31669 (8)0.0219 (3)
N2B0.26497 (11)0.03023 (11)0.37760 (7)0.0218 (3)
H2BB0.2806−0.01960.39790.026*
C1B0.23970 (13)0.10337 (13)0.28236 (9)0.0223 (4)
H1BA0.21960.15940.30080.027*
C2B0.24000 (13)0.09963 (13)0.22208 (9)0.0216 (4)
H2BA0.21980.15270.20040.026*
C3B0.27041 (13)0.01657 (13)0.19202 (9)0.0201 (4)
C4B0.30298 (13)−0.06058 (13)0.22507 (9)0.0202 (4)
H4BA0.3251−0.11500.20580.024*
C5B0.30286 (13)−0.05742 (13)0.28641 (9)0.0201 (4)
C6B0.26909 (12)0.02464 (13)0.31820 (9)0.0197 (4)
C7B0.23541 (14)0.11643 (13)0.40947 (9)0.0231 (4)
H7BA0.17470.13540.39570.028*
H7BB0.27770.16890.40130.028*
C8B0.23267 (14)0.09792 (13)0.47553 (9)0.0227 (4)
H8BA0.29380.08090.48940.027*
H8BB0.19200.04410.48350.027*
C9B0.19895 (16)0.18646 (14)0.50902 (10)0.0280 (4)
H9BA0.13720.20240.49560.034*
H9BB0.23870.24060.49990.034*
C10B0.19780 (17)0.17118 (15)0.57604 (10)0.0306 (5)
H10D0.17670.22890.59510.046*
H10E0.25890.15620.58970.046*
H10F0.15710.11890.58550.046*
C11B0.26655 (13)0.01152 (13)0.12696 (9)0.0212 (4)
O1C−0.01824 (11)0.07275 (10)0.44434 (7)0.0273 (3)
O2C0.04469 (11)−0.07447 (10)0.44094 (7)0.0272 (3)
H2C0.0378−0.07090.47690.041*
O3C0.13147 (10)−0.21295 (9)0.25882 (7)0.0262 (3)
O4C0.09802 (10)−0.15093 (10)0.17316 (7)0.0273 (3)
N1C0.09807 (11)−0.14756 (11)0.22802 (8)0.0209 (3)
N2C0.02634 (11)0.02410 (11)0.16522 (8)0.0217 (3)
H2CB0.0461−0.02390.14480.026*
C1C−0.00491 (13)0.09561 (13)0.25964 (9)0.0213 (4)
H1CA−0.02440.15150.24070.026*
C2C−0.00795 (13)0.09166 (13)0.32017 (10)0.0217 (4)
H2CA−0.02970.14440.34130.026*
C3C0.02148 (13)0.00852 (13)0.35102 (9)0.0204 (4)
C4C0.05534 (13)−0.06864 (13)0.31884 (10)0.0208 (4)
H4CA0.0757−0.12360.33850.025*
C5C0.05902 (12)−0.06455 (12)0.25737 (9)0.0196 (4)
C6C0.02695 (12)0.01732 (13)0.22475 (9)0.0199 (4)
C7C−0.00657 (14)0.11007 (14)0.13378 (9)0.0233 (4)
H7CA0.03360.16400.14280.028*
H7CB−0.06800.12620.14740.028*
C8C−0.00883 (14)0.09388 (14)0.06709 (9)0.0218 (4)
H8CA−0.04620.03780.05820.026*
H8CB0.05310.08160.05300.026*
C9C−0.04841 (15)0.18165 (14)0.03515 (10)0.0262 (4)
H9CA−0.11040.19320.04930.031*
H9CB−0.01150.23770.04500.031*
C10C−0.05119 (18)0.17027 (16)−0.03199 (10)0.0319 (5)
H10G−0.07510.2281−0.04960.048*
H10H−0.09010.1169−0.04230.048*
H10I0.00990.1587−0.04640.048*
C11C0.01442 (13)0.00514 (13)0.41585 (9)0.0209 (4)
O1D0.28378 (10)0.57136 (10)0.48734 (7)0.0265 (3)
O2D0.21231 (11)0.42785 (10)0.48256 (7)0.0274 (3)
H2D0.22080.43010.51850.041*
O3D0.11204 (11)0.29907 (10)0.29922 (7)0.0289 (3)
O4D0.15340 (10)0.35615 (10)0.21422 (7)0.0284 (3)
N1D0.15116 (11)0.36082 (12)0.26892 (8)0.0224 (3)
N2D0.22872 (11)0.52963 (11)0.20761 (7)0.0205 (3)
H2DB0.20940.48130.18730.025*
C1D0.26478 (13)0.59870 (13)0.30210 (9)0.0203 (4)
H1DA0.28570.65410.28330.024*
C2D0.26970 (13)0.59351 (13)0.36282 (9)0.0214 (4)
H2DA0.29380.64500.38420.026*
C3D0.23836 (13)0.51058 (13)0.39304 (9)0.0197 (4)
C4D0.20020 (13)0.43621 (13)0.36041 (9)0.0223 (4)
H4DA0.17800.38200.37990.027*
C5D0.19448 (13)0.44113 (13)0.29900 (9)0.0199 (4)
C6D0.22884 (12)0.52248 (13)0.26689 (9)0.0205 (4)
C7D0.25981 (13)0.61532 (13)0.17588 (9)0.0214 (4)
H7DA0.32260.63020.18750.026*
H7DB0.22130.66970.18650.026*
C8D0.25540 (14)0.59971 (13)0.10953 (9)0.0224 (4)
H8DA0.19220.58740.09780.027*
H8DB0.29180.54360.09920.027*
C9D0.29151 (16)0.68734 (14)0.07614 (10)0.0278 (4)
H9DA0.25360.74270.08560.033*
H9DB0.35380.70110.08940.033*
C10D0.29172 (18)0.67307 (15)0.00921 (10)0.0317 (5)
H10J0.31380.7306−0.00960.048*
H10K0.23030.6596−0.00420.048*
H10L0.33130.6201−0.00070.048*
C11D0.24632 (13)0.50516 (13)0.45793 (9)0.0213 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0316 (8)0.0284 (7)0.0246 (8)0.0040 (6)0.0033 (6)−0.0014 (6)
O2A0.0329 (8)0.0260 (7)0.0249 (8)0.0040 (6)0.0017 (6)0.0066 (6)
O3A0.0271 (7)0.0179 (6)0.0371 (9)0.0041 (5)0.0005 (6)0.0016 (6)
O4A0.0424 (9)0.0253 (7)0.0256 (8)0.0061 (6)0.0002 (7)−0.0037 (6)
N1A0.0208 (8)0.0168 (7)0.0295 (9)−0.0010 (6)0.0027 (7)0.0001 (6)
N2A0.0207 (8)0.0189 (7)0.0229 (9)−0.0003 (6)0.0003 (6)0.0000 (6)
C1A0.0182 (8)0.0164 (8)0.0270 (11)0.0000 (6)−0.0016 (7)0.0022 (7)
C2A0.0163 (8)0.0186 (8)0.0251 (10)−0.0014 (6)0.0019 (7)−0.0014 (7)
C3A0.0170 (8)0.0190 (8)0.0224 (10)−0.0030 (6)0.0019 (7)0.0028 (7)
C4A0.0163 (8)0.0174 (8)0.0264 (10)−0.0016 (6)0.0004 (7)0.0018 (7)
C5A0.0160 (8)0.0163 (8)0.0260 (10)−0.0013 (6)0.0015 (7)−0.0003 (7)
C6A0.0149 (8)0.0191 (8)0.0237 (10)−0.0019 (6)0.0020 (7)0.0015 (7)
C7A0.0213 (9)0.0183 (8)0.0245 (10)−0.0002 (7)−0.0010 (7)−0.0008 (7)
C8A0.0226 (9)0.0206 (8)0.0216 (10)−0.0002 (7)−0.0015 (7)0.0000 (7)
C9A0.0375 (12)0.0217 (9)0.0253 (11)0.0030 (8)−0.0012 (9)0.0002 (8)
C10A0.0430 (13)0.0249 (10)0.0261 (11)−0.0019 (9)−0.0025 (9)0.0039 (8)
C11A0.0182 (8)0.0201 (8)0.0241 (10)−0.0033 (7)0.0006 (7)0.0015 (7)
O1B0.0297 (8)0.0265 (7)0.0298 (8)0.0041 (6)−0.0016 (6)0.0041 (6)
O2B0.0349 (8)0.0223 (7)0.0248 (8)0.0011 (6)0.0011 (7)−0.0024 (6)
O3B0.0264 (7)0.0165 (6)0.0335 (8)0.0033 (5)0.0015 (6)−0.0009 (6)
O4B0.0440 (9)0.0250 (7)0.0302 (8)0.0064 (6)0.0038 (7)0.0065 (6)
N1B0.0206 (8)0.0149 (7)0.0303 (9)−0.0009 (6)−0.0013 (7)0.0001 (6)
N2B0.0224 (8)0.0169 (7)0.0261 (8)0.0019 (6)0.0006 (7)−0.0002 (6)
C1B0.0192 (9)0.0150 (8)0.0328 (11)0.0015 (6)0.0001 (8)−0.0042 (7)
C2B0.0157 (8)0.0186 (8)0.0304 (11)0.0003 (6)−0.0005 (7)0.0010 (7)
C3B0.0148 (8)0.0188 (8)0.0267 (10)−0.0023 (6)0.0018 (7)0.0008 (7)
C4B0.0147 (8)0.0158 (8)0.0300 (11)−0.0012 (6)0.0006 (7)−0.0019 (7)
C5B0.0172 (8)0.0157 (7)0.0276 (10)−0.0001 (6)−0.0010 (7)0.0014 (7)
C6B0.0138 (8)0.0179 (8)0.0275 (10)−0.0025 (6)0.0012 (7)0.0000 (7)
C7B0.0211 (9)0.0195 (8)0.0287 (10)0.0005 (7)0.0002 (8)−0.0027 (8)
C8B0.0202 (9)0.0191 (8)0.0287 (10)0.0015 (7)0.0012 (8)−0.0025 (8)
C9B0.0309 (11)0.0218 (9)0.0312 (11)0.0011 (8)0.0012 (9)−0.0025 (8)
C10B0.0390 (12)0.0239 (9)0.0290 (11)−0.0003 (9)0.0026 (9)−0.0037 (8)
C11B0.0157 (8)0.0193 (8)0.0285 (10)−0.0017 (7)0.0007 (7)−0.0002 (7)
O1C0.0317 (8)0.0221 (7)0.0282 (8)0.0061 (6)0.0018 (6)−0.0016 (6)
O2C0.0331 (8)0.0204 (7)0.0281 (8)0.0032 (6)0.0015 (7)0.0023 (6)
O3C0.0267 (7)0.0160 (6)0.0358 (8)0.0032 (5)0.0022 (6)0.0019 (6)
O4C0.0281 (8)0.0236 (7)0.0303 (8)0.0024 (6)0.0025 (6)−0.0055 (6)
N1C0.0167 (7)0.0154 (7)0.0306 (9)−0.0019 (5)0.0015 (6)−0.0012 (6)
N2C0.0218 (8)0.0166 (7)0.0268 (9)0.0027 (6)0.0019 (7)−0.0012 (6)
C1C0.0188 (8)0.0175 (8)0.0276 (11)0.0014 (6)0.0015 (7)0.0022 (7)
C2C0.0181 (8)0.0160 (8)0.0309 (11)0.0002 (6)0.0004 (8)−0.0018 (7)
C3C0.0166 (8)0.0170 (8)0.0277 (10)−0.0006 (6)0.0011 (7)0.0003 (7)
C4C0.0170 (8)0.0161 (8)0.0295 (11)−0.0023 (6)−0.0005 (7)0.0008 (7)
C5C0.0162 (8)0.0142 (7)0.0283 (10)−0.0011 (6)0.0022 (7)−0.0011 (7)
C6C0.0137 (8)0.0176 (8)0.0283 (11)−0.0021 (6)0.0019 (7)−0.0001 (7)
C7C0.0204 (9)0.0200 (8)0.0295 (11)0.0018 (7)0.0001 (8)0.0000 (8)
C8C0.0201 (9)0.0199 (8)0.0254 (10)0.0000 (7)0.0015 (7)−0.0003 (7)
C9C0.0288 (10)0.0201 (9)0.0298 (11)0.0029 (7)0.0012 (8)0.0013 (8)
C10C0.0395 (12)0.0248 (10)0.0315 (12)0.0023 (9)−0.0011 (10)0.0027 (9)
C11C0.0168 (8)0.0188 (8)0.0270 (10)−0.0022 (7)0.0003 (7)0.0012 (7)
O1D0.0279 (8)0.0255 (7)0.0261 (8)−0.0049 (6)0.0008 (6)0.0000 (6)
O2D0.0314 (8)0.0233 (7)0.0274 (8)−0.0038 (6)0.0018 (7)0.0057 (6)
O3D0.0279 (7)0.0193 (6)0.0396 (9)−0.0054 (5)0.0020 (7)0.0019 (6)
O4D0.0275 (8)0.0247 (7)0.0330 (9)−0.0030 (6)−0.0003 (6)−0.0042 (6)
N1D0.0168 (7)0.0169 (7)0.0333 (10)0.0006 (6)0.0005 (7)−0.0003 (6)
N2D0.0196 (7)0.0174 (7)0.0245 (8)−0.0010 (6)0.0017 (6)−0.0015 (6)
C1D0.0184 (8)0.0164 (8)0.0261 (10)−0.0003 (6)0.0020 (7)0.0017 (7)
C2D0.0174 (8)0.0174 (8)0.0295 (10)0.0006 (6)0.0019 (7)−0.0024 (7)
C3D0.0168 (8)0.0177 (8)0.0245 (9)0.0014 (6)0.0037 (7)0.0007 (7)
C4D0.0159 (8)0.0174 (8)0.0336 (11)0.0014 (6)0.0018 (8)0.0019 (7)
C5D0.0152 (8)0.0162 (8)0.0283 (10)0.0006 (6)0.0023 (7)−0.0021 (7)
C6D0.0140 (8)0.0195 (8)0.0280 (10)0.0018 (6)0.0025 (7)−0.0007 (7)
C7D0.0191 (9)0.0192 (8)0.0260 (10)0.0000 (7)0.0029 (7)0.0002 (7)
C8D0.0198 (9)0.0186 (8)0.0287 (10)0.0002 (7)0.0017 (8)−0.0005 (7)
C9D0.0324 (11)0.0212 (9)0.0299 (11)−0.0019 (8)0.0019 (9)0.0021 (8)
C10D0.0410 (13)0.0240 (9)0.0303 (12)0.0002 (9)0.0007 (10)0.0029 (8)
C11D0.0166 (8)0.0176 (8)0.0297 (10)0.0038 (6)0.0020 (7)0.0015 (7)

Geometric parameters (Å, °)

O1A—C11A1.256 (2)O1C—C11C1.234 (2)
O2A—C11A1.295 (2)O2C—C11C1.316 (2)
O2A—H2A0.82O2C—H2C0.82
O3A—N1A1.239 (2)O3C—N1C1.241 (2)
O4A—N1A1.238 (2)O4C—N1C1.239 (2)
N1A—C5A1.450 (2)N1C—C5C1.446 (2)
N2A—C6A1.338 (3)N2C—C6C1.347 (3)
N2A—C7A1.459 (2)N2C—C7C1.467 (2)
N2A—H2AB0.86N2C—H2CB0.86
C1A—C2A1.374 (3)C1C—C2C1.368 (3)
C1A—C6A1.424 (3)C1C—C6C1.420 (3)
C1A—H1AA0.93C1C—H1CA0.93
C2A—C3A1.412 (3)C2C—C3C1.413 (3)
C2A—H2AA0.93C2C—H2CA0.93
C3A—C4A1.378 (3)C3C—C4C1.385 (3)
C3A—C11A1.473 (3)C3C—C11C1.468 (3)
C4A—C5A1.388 (3)C4C—C5C1.390 (3)
C4A—H4AA0.93C4C—H4CA0.93
C5A—C6A1.430 (3)C5C—C6C1.431 (3)
C7A—C8A1.526 (3)C7C—C8C1.522 (3)
C7A—H7AA0.97C7C—H7CA0.97
C7A—H7AB0.97C7C—H7CB0.97
C8A—C9A1.515 (3)C8C—C9C1.527 (3)
C8A—H8AA0.97C8C—H8CA0.97
C8A—H8AB0.97C8C—H8CB0.97
C9A—C10A1.534 (3)C9C—C10C1.524 (3)
C9A—H9AA0.97C9C—H9CA0.97
C9A—H9AB0.97C9C—H9CB0.97
C10A—H10A0.96C10C—H10G0.96
C10A—H10B0.96C10C—H10H0.96
C10A—H10C0.96C10C—H10I0.96
O1B—C11B1.251 (2)O1D—C11D1.256 (2)
O2B—C11B1.300 (2)O2D—C11D1.306 (2)
O2B—H2B0.82O2D—H2D0.82
O3B—N1B1.233 (2)O3D—N1D1.236 (2)
O4B—N1B1.238 (2)O4D—N1D1.237 (2)
N1B—C5B1.444 (2)N1D—C5D1.447 (2)
N2B—C6B1.344 (3)N2D—C6D1.342 (3)
N2B—C7B1.461 (2)N2D—C7D1.461 (2)
N2B—H2BB0.86N2D—H2DB0.86
C1B—C2B1.362 (3)C1D—C2D1.374 (3)
C1B—C6B1.424 (3)C1D—C6D1.421 (3)
C1B—H1BA0.93C1D—H1DA0.93
C2B—C3B1.410 (3)C2D—C3D1.414 (3)
C2B—H2BA0.93C2D—H2DA0.93
C3B—C4B1.387 (3)C3D—C4D1.383 (3)
C3B—C11B1.471 (3)C3D—C11D1.470 (3)
C4B—C5B1.385 (3)C4D—C5D1.390 (3)
C4B—H4BA0.93C4D—H4DA0.93
C5B—C6B1.434 (3)C5D—C6D1.432 (3)
C7B—C8B1.514 (3)C7D—C8D1.514 (3)
C7B—H7BA0.97C7D—H7DA0.97
C7B—H7BB0.97C7D—H7DB0.97
C8B—C9B1.525 (3)C8D—C9D1.525 (3)
C8B—H8BA0.97C8D—H8DA0.97
C8B—H8BB0.97C8D—H8DB0.97
C9B—C10B1.527 (3)C9D—C10D1.523 (3)
C9B—H9BA0.97C9D—H9DA0.97
C9B—H9BB0.97C9D—H9DB0.97
C10B—H10D0.96C10D—H10J0.96
C10B—H10E0.96C10D—H10K0.96
C10B—H10F0.96C10D—H10L0.96
C11A—O2A—H2A109.5C11C—O2C—H2C109.5
O4A—N1A—O3A122.31 (17)O4C—N1C—O3C122.07 (16)
O4A—N1A—C5A119.18 (16)O4C—N1C—C5C119.29 (16)
O3A—N1A—C5A118.50 (17)O3C—N1C—C5C118.63 (17)
C6A—N2A—C7A124.42 (17)C6C—N2C—C7C122.69 (16)
C6A—N2A—H2AB117.8C6C—N2C—H2CB118.7
C7A—N2A—H2AB117.8C7C—N2C—H2CB118.7
C2A—C1A—C6A121.92 (17)C2C—C1C—C6C122.32 (18)
C2A—C1A—H1AA119.0C2C—C1C—H1CA118.8
C6A—C1A—H1AA119.0C6C—C1C—H1CA118.8
C1A—C2A—C3A120.92 (18)C1C—C2C—C3C120.92 (18)
C1A—C2A—H2AA119.5C1C—C2C—H2CA119.5
C3A—C2A—H2AA119.5C3C—C2C—H2CA119.5
C4A—C3A—C2A118.93 (19)C4C—C3C—C2C118.71 (19)
C4A—C3A—C11A120.07 (17)C4C—C3C—C11C121.61 (17)
C2A—C3A—C11A121.00 (17)C2C—C3C—C11C119.68 (17)
C3A—C4A—C5A120.41 (18)C3C—C4C—C5C120.46 (18)
C3A—C4A—H4AA119.8C3C—C4C—H4CA119.8
C5A—C4A—H4AA119.8C5C—C4C—H4CA119.8
C4A—C5A—C6A122.44 (17)C4C—C5C—C6C122.16 (17)
C4A—C5A—N1A116.05 (17)C4C—C5C—N1C116.21 (17)
C6A—C5A—N1A121.51 (18)C6C—C5C—N1C121.63 (18)
N2A—C6A—C1A120.29 (17)N2C—C6C—C1C119.90 (17)
N2A—C6A—C5A124.49 (18)N2C—C6C—C5C124.72 (17)
C1A—C6A—C5A115.21 (18)C1C—C6C—C5C115.37 (18)
N2A—C7A—C8A110.12 (16)N2C—C7C—C8C111.33 (16)
N2A—C7A—H7AA109.6N2C—C7C—H7CA109.4
C8A—C7A—H7AA109.6C8C—C7C—H7CA109.4
N2A—C7A—H7AB109.6N2C—C7C—H7CB109.4
C8A—C7A—H7AB109.6C8C—C7C—H7CB109.4
H7AA—C7A—H7AB108.1H7CA—C7C—H7CB108.0
C9A—C8A—C7A112.02 (16)C7C—C8C—C9C110.83 (16)
C9A—C8A—H8AA109.2C7C—C8C—H8CA109.5
C7A—C8A—H8AA109.2C9C—C8C—H8CA109.5
C9A—C8A—H8AB109.2C7C—C8C—H8CB109.5
C7A—C8A—H8AB109.2C9C—C8C—H8CB109.5
H8AA—C8A—H8AB107.9H8CA—C8C—H8CB108.1
C8A—C9A—C10A112.47 (17)C10C—C9C—C8C113.28 (17)
C8A—C9A—H9AA109.1C10C—C9C—H9CA108.9
C10A—C9A—H9AA109.1C8C—C9C—H9CA108.9
C8A—C9A—H9AB109.1C10C—C9C—H9CB108.9
C10A—C9A—H9AB109.1C8C—C9C—H9CB108.9
H9AA—C9A—H9AB107.8H9CA—C9C—H9CB107.7
C9A—C10A—H10A109.5C9C—C10C—H10G109.5
C9A—C10A—H10B109.5C9C—C10C—H10H109.5
H10A—C10A—H10B109.5H10G—C10C—H10H109.5
C9A—C10A—H10C109.5C9C—C10C—H10I109.5
H10A—C10A—H10C109.5H10G—C10C—H10I109.5
H10B—C10A—H10C109.5H10H—C10C—H10I109.5
O1A—C11A—O2A123.22 (19)O1C—C11C—O2C122.87 (19)
O1A—C11A—C3A120.06 (17)O1C—C11C—C3C121.59 (17)
O2A—C11A—C3A116.72 (17)O2C—C11C—C3C115.54 (17)
C11B—O2B—H2B109.5C11D—O2D—H2D109.5
O3B—N1B—O4B121.60 (16)O3D—N1D—O4D121.99 (17)
O3B—N1B—C5B118.91 (17)O3D—N1D—C5D118.31 (17)
O4B—N1B—C5B119.48 (16)O4D—N1D—C5D119.70 (16)
C6B—N2B—C7B123.53 (16)C6D—N2D—C7D123.37 (16)
C6B—N2B—H2BB118.2C6D—N2D—H2DB118.3
C7B—N2B—H2BB118.2C7D—N2D—H2DB118.3
C2B—C1B—C6B122.43 (18)C2D—C1D—C6D122.42 (17)
C2B—C1B—H1BA118.8C2D—C1D—H1DA118.8
C6B—C1B—H1BA118.8C6D—C1D—H1DA118.8
C1B—C2B—C3B120.95 (18)C1D—C2D—C3D120.55 (18)
C1B—C2B—H2BA119.5C1D—C2D—H2DA119.7
C3B—C2B—H2BA119.5C3D—C2D—H2DA119.7
C4B—C3B—C2B118.65 (18)C4D—C3D—C2D118.67 (18)
C4B—C3B—C11B120.77 (17)C4D—C3D—C11D121.47 (17)
C2B—C3B—C11B120.58 (17)C2D—C3D—C11D119.86 (17)
C5B—C4B—C3B120.75 (17)C3D—C4D—C5D121.11 (18)
C5B—C4B—H4BA119.6C3D—C4D—H4DA119.4
C3B—C4B—H4BA119.6C5D—C4D—H4DA119.4
C4B—C5B—C6B121.82 (17)C4D—C5D—C6D121.58 (17)
C4B—C5B—N1B116.48 (16)C4D—C5D—N1D117.00 (17)
C6B—C5B—N1B121.71 (17)C6D—C5D—N1D121.42 (17)
N2B—C6B—C1B120.51 (17)N2D—C6D—C1D120.10 (17)
N2B—C6B—C5B124.17 (17)N2D—C6D—C5D124.32 (17)
C1B—C6B—C5B115.32 (18)C1D—C6D—C5D115.58 (17)
N2B—C7B—C8B110.78 (16)N2D—C7D—C8D110.88 (16)
N2B—C7B—H7BA109.5N2D—C7D—H7DA109.5
C8B—C7B—H7BA109.5C8D—C7D—H7DA109.5
N2B—C7B—H7BB109.5N2D—C7D—H7DB109.5
C8B—C7B—H7BB109.5C8D—C7D—H7DB109.5
H7BA—C7B—H7BB108.1H7DA—C7D—H7DB108.1
C7B—C8B—C9B111.18 (16)C7D—C8D—C9D111.18 (16)
C7B—C8B—H8BA109.4C7D—C8D—H8DA109.4
C9B—C8B—H8BA109.4C9D—C8D—H8DA109.4
C7B—C8B—H8BB109.4C7D—C8D—H8DB109.4
C9B—C8B—H8BB109.4C9D—C8D—H8DB109.4
H8BA—C8B—H8BB108.0H8DA—C8D—H8DB108.0
C8B—C9B—C10B112.58 (17)C10D—C9D—C8D112.85 (17)
C8B—C9B—H9BA109.1C10D—C9D—H9DA109.0
C10B—C9B—H9BA109.1C8D—C9D—H9DA109.0
C8B—C9B—H9BB109.1C10D—C9D—H9DB109.0
C10B—C9B—H9BB109.1C8D—C9D—H9DB109.0
H9BA—C9B—H9BB107.8H9DA—C9D—H9DB107.8
C9B—C10B—H10D109.5C9D—C10D—H10J109.5
C9B—C10B—H10E109.5C9D—C10D—H10K109.5
H10D—C10B—H10E109.5H10J—C10D—H10K109.5
C9B—C10B—H10F109.5C9D—C10D—H10L109.5
H10D—C10B—H10F109.5H10J—C10D—H10L109.5
H10E—C10B—H10F109.5H10K—C10D—H10L109.5
O1B—C11B—O2B123.35 (19)O1D—C11D—O2D122.66 (18)
O1B—C11B—C3B120.57 (18)O1D—C11D—C3D121.40 (17)
O2B—C11B—C3B116.07 (17)O2D—C11D—C3D115.94 (17)
C6A—C1A—C2A—C3A1.9 (3)C6C—C1C—C2C—C3C0.4 (3)
C1A—C2A—C3A—C4A1.6 (3)C1C—C2C—C3C—C4C1.2 (3)
C1A—C2A—C3A—C11A−177.65 (17)C1C—C2C—C3C—C11C−177.89 (17)
C2A—C3A—C4A—C5A−2.3 (3)C2C—C3C—C4C—C5C−0.8 (3)
C11A—C3A—C4A—C5A176.92 (17)C11C—C3C—C4C—C5C178.28 (17)
C3A—C4A—C5A—C6A−0.4 (3)C3C—C4C—C5C—C6C−1.2 (3)
C3A—C4A—C5A—N1A179.24 (16)C3C—C4C—C5C—N1C178.17 (16)
O4A—N1A—C5A—C4A167.58 (17)O4C—N1C—C5C—C4C175.51 (16)
O3A—N1A—C5A—C4A−13.0 (2)O3C—N1C—C5C—C4C−5.2 (2)
O4A—N1A—C5A—C6A−12.8 (3)O4C—N1C—C5C—C6C−5.1 (3)
O3A—N1A—C5A—C6A166.64 (17)O3C—N1C—C5C—C6C174.24 (16)
C7A—N2A—C6A—C1A5.5 (3)C7C—N2C—C6C—C1C−0.2 (3)
C7A—N2A—C6A—C5A−173.76 (17)C7C—N2C—C6C—C5C−179.46 (17)
C2A—C1A—C6A—N2A176.23 (18)C2C—C1C—C6C—N2C178.34 (18)
C2A—C1A—C6A—C5A−4.4 (3)C2C—C1C—C6C—C5C−2.3 (3)
C4A—C5A—C6A—N2A−176.99 (18)C4C—C5C—C6C—N2C−177.97 (17)
N1A—C5A—C6A—N2A3.4 (3)N1C—C5C—C6C—N2C2.7 (3)
C4A—C5A—C6A—C1A3.7 (3)C4C—C5C—C6C—C1C2.7 (3)
N1A—C5A—C6A—C1A−175.93 (16)N1C—C5C—C6C—C1C−176.62 (16)
C6A—N2A—C7A—C8A−179.73 (17)C6C—N2C—C7C—C8C−174.03 (17)
N2A—C7A—C8A—C9A−178.77 (17)N2C—C7C—C8C—C9C176.71 (16)
C7A—C8A—C9A—C10A−178.04 (18)C7C—C8C—C9C—C10C179.19 (18)
C4A—C3A—C11A—O1A−176.17 (18)C4C—C3C—C11C—O1C−177.83 (19)
C2A—C3A—C11A—O1A3.1 (3)C2C—C3C—C11C—O1C1.3 (3)
C4A—C3A—C11A—O2A3.8 (3)C4C—C3C—C11C—O2C1.9 (3)
C2A—C3A—C11A—O2A−176.93 (17)C2C—C3C—C11C—O2C−179.03 (17)
C6B—C1B—C2B—C3B−0.4 (3)C6D—C1D—C2D—C3D−0.2 (3)
C1B—C2B—C3B—C4B−2.0 (3)C1D—C2D—C3D—C4D−1.9 (3)
C1B—C2B—C3B—C11B177.20 (17)C1D—C2D—C3D—C11D178.42 (17)
C2B—C3B—C4B—C5B2.1 (3)C2D—C3D—C4D—C5D1.6 (3)
C11B—C3B—C4B—C5B−177.16 (17)C11D—C3D—C4D—C5D−178.79 (17)
C3B—C4B—C5B—C6B0.3 (3)C3D—C4D—C5D—C6D0.9 (3)
C3B—C4B—C5B—N1B−179.51 (16)C3D—C4D—C5D—N1D−178.39 (16)
O3B—N1B—C5B—C4B10.2 (3)O3D—N1D—C5D—C4D8.8 (3)
O4B—N1B—C5B—C4B−170.94 (17)O4D—N1D—C5D—C4D−171.89 (17)
O3B—N1B—C5B—C6B−169.60 (16)O3D—N1D—C5D—C6D−170.48 (16)
O4B—N1B—C5B—C6B9.3 (3)O4D—N1D—C5D—C6D8.9 (3)
C7B—N2B—C6B—C1B−3.1 (3)C7D—N2D—C6D—C1D−3.3 (3)
C7B—N2B—C6B—C5B176.30 (17)C7D—N2D—C6D—C5D176.76 (17)
C2B—C1B—C6B—N2B−177.90 (18)C2D—C1D—C6D—N2D−177.50 (17)
C2B—C1B—C6B—C5B2.6 (3)C2D—C1D—C6D—C5D2.4 (3)
C4B—C5B—C6B—N2B177.98 (17)C4D—C5D—C6D—N2D177.14 (18)
N1B—C5B—C6B—N2B−2.3 (3)N1D—C5D—C6D—N2D−3.6 (3)
C4B—C5B—C6B—C1B−2.5 (3)C4D—C5D—C6D—C1D−2.8 (3)
N1B—C5B—C6B—C1B177.21 (16)N1D—C5D—C6D—C1D176.42 (16)
C6B—N2B—C7B—C8B176.51 (17)C6D—N2D—C7D—C8D177.42 (17)
N2B—C7B—C8B—C9B−178.18 (17)N2D—C7D—C8D—C9D−177.64 (16)
C7B—C8B—C9B—C10B−178.45 (18)C7D—C8D—C9D—C10D177.78 (18)
C4B—C3B—C11B—O1B176.75 (18)C4D—C3D—C11D—O1D177.59 (18)
C2B—C3B—C11B—O1B−2.5 (3)C2D—C3D—C11D—O1D−2.8 (3)
C4B—C3B—C11B—O2B−3.0 (3)C4D—C3D—C11D—O2D−2.4 (3)
C2B—C3B—C11B—O2B177.81 (17)C2D—C3D—C11D—O2D177.29 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2A—H2A···O1Ai0.821.802.613 (2)168
O2B—H2B···O1Dii0.821.812.624 (2)172
O2C—H2C···O1Ciii0.821.802.619 (2)175
O2D—H2D···O1Biv0.821.802.612 (2)173
C1A—H1AA···O3Av0.932.463.290 (2)149
C1C—H1CA···O3Cvi0.932.443.256 (2)146
C1D—H1DA···O3Bvii0.932.403.227 (2)148
N2A—H2AB···O4A0.862.022.656 (2)130
N2B—H2BB···O4B0.862.012.651 (2)130
N2C—H2CB···O4C0.862.022.649 (2)129
N2D—H2DB···O4D0.862.012.649 (2)130
C1B—H1BA···O3D0.932.493.311 (2)147
C7D—H7DA···Cg1v0.972.813.584 (2)137
C7C—H7CB···Cg2viii0.972.883.621 (2)134

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, −y+1/2, z−1/2; (iii) −x, −y, −z+1; (iv) x, −y+1/2, z+1/2; (v) −x+1, y+1/2, −z+1/2; (vi) −x, y+1/2, −z+1/2; (vii) x, y+1, z; (viii) −x, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2784).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst.19, 105–107.
  • Ishida, T., Suzuki, T., Hirashima, S., Mizutani, K., Yoshida, A., Ando, I., Ikeda, S., Adachi, T. & Hashimoto, H. (2006). Bioorg. Med. Chem. Lett.16, 1859–1863. [PubMed]
  • Mohd Maidin, S. M., Abdul Rahim, A. S., Osman, H., Kia, R. & Fun, H.-K. (2008). Acta Cryst. E64, o1550–o1551. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography