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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 1| January 2013| Pages o144-o145

(R,R)-1-Acetyl-1′-(2,4,6-tri­nitro­phen­yl)-2,2′-bipyrrolidine

aDepartment of Organic Chemistry, Gdańsk University of Technology, 80-233 Gdańsk, Poland, and bFaculty of Chemistry, Adam Mickiewicz University, 60-780 Poznań, Poland
*Correspondence e-mail: kateichs@student.pg.gda.pl

(Received 3 December 2012; accepted 18 December 2012; online 22 December 2012)

The structure of the title mol­ecule, C16H19N5O7, is mainly determined by the steric effect of a bulky 2,4,6-trinitro­phenyl group attached to the N atom of a pyrrolidine ring. Both pyrrolidine rings adopt an envelope conformation, with one of the methylene C atoms as the flap in each case, and the N—C—C—N torsion angle along the bond connecting the two pyrrolidine rings is −174.9 (2)°. The benzene ring of the 2,3,5-trinitro­phenyl substituent is deformed and the r.m.s. deviation of its six atoms from the best plane is 0.026 Å. The N atoms of the two nitro groups in the ortho positions deviate from the best plane of the benzene ring by −0.033 (5) and 0.385 (5) Å. These groups, as well as the pyrrolidine ring, are twisted relative to the aromatic ring in the same direction, their best planes forming dihedral angles of 30.2 (2), 64.8 (1) and 46.6 (2)°, respectively, with the ring. An intra­molecular C—H⋯O hydrogen bond occurs. In the crystal, there is a short [O⋯C = 3.019 (4) Å] contact between a nitro O atom and a C atom of the benzene ring bearing the nitro group and a C—H⋯O inter­action between a methyl H atom and another nitro O atom.

Related literature

For crystal structures of related 1-amino-2,4,6-trinitro­benzenes, see: Butcher et al. (1992[Butcher, R. J., Gilardi, R., Flippen-Anderson, J. L. & George, C. (1992). New J. Chem. 16, 679-692.]); Baggio et al. (1997[Baggio, R., Remedi, M. V., Garland, M. T. & Bujan, E. I. (1997). J. Chem. Crystallogr. 27, 499-505.]).

[Scheme 1]

Experimental

Crystal data
  • C16H19N5O7

  • Mr = 393.36

  • Orthorhombic, P 21 21 21

  • a = 8.1989 (5) Å

  • b = 10.4442 (6) Å

  • c = 20.8877 (13) Å

  • V = 1788.63 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 293 K

  • 0.20 × 0.20 × 0.15 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.990, Tmax = 1.000

  • 7678 measured reflections

  • 1818 independent reflections

  • 1477 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.090

  • S = 1.06

  • 1818 reflections

  • 254 parameters

  • H-atom parameters constrained

  • Δρmax = 0.14 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯O1 0.98 2.18 2.891 (4) 129
C18—H18C⋯O2i 0.96 2.51 3.454 (5) 168
Symmetry code: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title compound was synthesized as a part of a project aiming at the application of 2,4,6-trinitrophenyl chromophore for determination of absolute configuration of secondary diamines. The molecular structure of the title compound is shown in Fig. 1. Both pyrrolidine rings adopt an envelope conformation with the methylene C4 and C9 atoms forming a flap in each of the five-membered rings, respectively. The N7—C6—C2—N1 torsion angle along the bond connecting two pyrrolidine rings is -174.9 (2)°.

The benzene ring of the 2,3,5-trinitrophenyl substituent shows large deformation from planarity with r.m.s. deviation of 0.026 Å for the six fitted atoms and the maximum deviation from the best plane of 0.038 (2) Å for C11. Whereas N3 and N4 atoms of the nitro groups are vitrually in the mean plane of the benzene ring [their deviations from the plane being -0.050 (5), -0.033 (5) Å, respectively] the N1 atom from the pyrrolidine substituent and the N2 atom from one of the ortho nitro groups deviate strongly from this plane [deviations of -0.168 (4) and 0.385 (5) Å, respectively] reflecting steric effects within this overcrowded molecule. The nitro groups attached to C12 and C16 of the benzene ring are twisted in the same direction as the pyrrolidine ring attached to C11 forming the fragment of a propeller. The dihedral angles formed by these nitro groups and the planar C11, N1, C2, C5 fragment are 30.2 (2), 64.8 (1) 46.6 (2)°, respectively. The nitro group attached to C14 is only slightly twisted relative to the benzene ring with the dihedral angle of 4.9 (2)°. The conformation adopted by the molecule leads to two short intermolecular contacts between the pyrrolidine ring H atoms and O toms of the ortho nitro-groups (Table 1). Interestingly, the release of strain in the title molecule occurs differently than in 1-pyrrolidino-2,4,6-trinitrobenzene (Baggio et al., 1997) where the benzene ring adopted a sofa form with the flap formed by the C atom to which the pyrrolidine ring was attached. On the other hand, the release of strain is similar to that observed for N,N-dimethyl-2,4,6-trinitroaniline (Butcher et al., 1992), 1-piperidylo-2,4,6-trinitrobenzene and 1-morpholino-2,4,6-trinitrobenzene (Baggio et al., 1997)

Two short intermolecular contacts are observed in this crystal structure. One, O1···.C16(1/2 + x, 3/2 - y, 2 - z) of 3.019 (4) Å, is formed between the nitro group O atom and the carbon atom of the benzene ring bearing the nitro group. The second one, H18C···.O2(2 - x, 1/2 + y, 3/2 - z) of 2.51 Å, is formed between the methyl group H atom and the nitro group O atom. The crystal packing in the studied crystal is shown in Fig. 2.

Related literature top

For crystal structures of related 1-amino-2,4,6-trinitrobenzenes, see: Butcher et al. (1992); Baggio et al. (1997).

Experimental top

A mixture of (R,R)-2,2'-bipyrrolidine hydrochloride (280 mg, 1.31 mmol), 1-chloro-2,4,6-trinitrobenzene (650 mg, 2.63 mmol) and anhydrous sodium acetate (860 mg, 10.50 mmol) in anhydrous ethanol (10 ml) was heated under reflux for 30 min. The resulting suspension was cooled to room temperature and water (15 ml) was added into it. The aqueous layer was extracted with dichloromethane (2 x 15 ml). The combined organic extracts were dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal the solvent in vacuo afforded the crude product, which was purified by means of column chromatography on silica gel using ethyl acetate to yield 0.12 g (23%) of product as a yellow solid. Crystals suitable for X-ray diffraction analysis were obtained by allowing a refluxed solution of the product in ethyl acetate to cool slowly at room temperature (without temperature control) and allowing the solvent to evaporate for 20 h, 1H NMR: (CDCl3, 500 MHz) δ: 8.66 (s, 2H); 4.49 (q, J=6.8 Hz, 1H); 4.09 (q, J=6.0 Hz, 1H); 3.56 (m, 1H); 3.43 (m, 1H); 3.36 (m, 1H); 3.20 (t, J=8.3 Hz, 1H); 2.10 (m, 2H); 1.92 (s, 3H); 1,88 (m, 5H); 1.73 (m, 1H), [α]D20 = -1430 (c 0.2 e thyl acetate).

Refinement top

All H atoms were located in electron-density difference maps, however for further refinement their positions were determined geometrically with C—H bond lengths of 0.93 - 0.97 Å. All H atoms were refined in the riding-model approximation, with Uiso(H)=1.5Ueq(Cmethyl) or Uiso(H)=1.2Ueq(C) for the remaining H atoms. In the absence of significant anomalous dispersion effects, 1319 Friedel pairs were merged.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids shown at the 50% probability level.
[Figure 2] Fig. 2. Crystal packing shown along the a axis. Short intermolecular contacts are shown as dashed lines.
(R,R)-1-Acetyl-1'-(2,4,6-trinitrophenyl)-2,2'-bipyrrolidine top
Crystal data top
C16H19N5O7F(000) = 824
Mr = 393.36Dx = 1.461 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1951 reflections
a = 8.1989 (5) Åθ = 2.9–28.7°
b = 10.4442 (6) ŵ = 0.12 mm1
c = 20.8877 (13) ÅT = 293 K
V = 1788.63 (19) Å3Tabloid, orange
Z = 40.20 × 0.20 × 0.15 mm
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
1818 independent reflections
Radiation source: Enhance (Mo) X-ray Source1477 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 16.1544 pixels mm-1θmax = 25.0°, θmin = 4.3°
ω scanh = 99
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 1212
Tmin = 0.990, Tmax = 1.000l = 2424
7678 measured reflections
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0351P)2 + 0.2637P]
where P = (Fo2 + 2Fc2)/3
1818 reflections(Δ/σ)max = 0.001
254 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C16H19N5O7V = 1788.63 (19) Å3
Mr = 393.36Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.1989 (5) ŵ = 0.12 mm1
b = 10.4442 (6) ÅT = 293 K
c = 20.8877 (13) Å0.20 × 0.20 × 0.15 mm
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
1818 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
1477 reflections with I > 2σ(I)
Tmin = 0.990, Tmax = 1.000Rint = 0.040
7678 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.090H-atom parameters constrained
S = 1.06Δρmax = 0.14 e Å3
1818 reflectionsΔρmin = 0.16 e Å3
254 parameters
Special details top

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) top
xyzUiso*/Ueq
N10.6350 (3)0.9926 (2)0.95416 (11)0.0336 (6)
C20.7856 (4)1.0547 (3)0.93068 (14)0.0360 (8)
H20.87400.99150.93090.043*
C30.8200 (5)1.1543 (3)0.98208 (15)0.0496 (10)
H3A0.93611.17040.98600.060*
H3B0.76471.23430.97270.060*
C40.7528 (5)1.0932 (4)1.04212 (16)0.0520 (10)
H4A0.73351.15661.07520.062*
H4B0.82641.02831.05850.062*
C50.5943 (5)1.0343 (4)1.01938 (16)0.0498 (10)
H5A0.56280.96231.04600.060*
H5B0.50681.09681.01910.060*
C60.7620 (4)1.1031 (3)0.86178 (15)0.0378 (8)
H60.72691.03130.83490.045*
N70.9150 (4)1.1543 (3)0.83607 (13)0.0429 (7)
C80.9020 (6)1.2884 (4)0.81637 (19)0.0625 (12)
H8A0.89981.29570.77010.075*
H8B0.99281.33810.83280.075*
C90.7443 (6)1.3326 (4)0.8449 (2)0.0804 (15)
H9A0.69041.39290.81660.097*
H9B0.76321.37400.88590.097*
C100.6410 (5)1.2131 (4)0.85355 (18)0.0562 (10)
H10A0.57261.19910.81630.067*
H10B0.57191.22090.89100.067*
C110.5621 (4)0.8893 (3)0.92546 (13)0.0300 (7)
C120.6456 (4)0.7851 (3)0.89814 (14)0.0331 (7)
C130.5699 (4)0.6911 (3)0.86275 (15)0.0362 (8)
H130.63100.62700.84320.043*
C140.4047 (4)0.6931 (3)0.85668 (14)0.0330 (7)
C150.3111 (4)0.7849 (3)0.88681 (14)0.0350 (8)
H150.19780.78230.88490.042*
C160.3898 (4)0.8793 (3)0.91946 (14)0.0332 (8)
C171.0360 (5)1.0730 (5)0.81772 (16)0.0562 (11)
C181.1766 (6)1.1325 (5)0.78229 (19)0.0863 (16)
H18A1.26471.07210.77960.129*
H18B1.21271.20760.80470.129*
H18C1.14231.15570.73990.129*
O10.8695 (3)0.7949 (2)0.96552 (12)0.0539 (7)
O20.8947 (3)0.6887 (3)0.87822 (14)0.0715 (9)
O30.4126 (4)0.5153 (3)0.79145 (14)0.0718 (9)
O40.1779 (3)0.5873 (3)0.81795 (14)0.0696 (9)
O50.3003 (4)1.0886 (2)0.92558 (14)0.0613 (8)
O60.1894 (3)0.9500 (3)0.98862 (14)0.0702 (9)
O71.0284 (4)0.9579 (3)0.82913 (13)0.0685 (8)
N20.8176 (4)0.7573 (3)0.91450 (16)0.0424 (7)
N30.3249 (4)0.5912 (3)0.81954 (13)0.0425 (7)
N40.2857 (4)0.9810 (3)0.94709 (15)0.0451 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0302 (16)0.0338 (14)0.0369 (14)0.0035 (12)0.0035 (13)0.0049 (13)
C20.0333 (19)0.0329 (17)0.0416 (18)0.0042 (15)0.0008 (16)0.0035 (15)
C30.056 (3)0.047 (2)0.0456 (19)0.0165 (19)0.0053 (19)0.0037 (18)
C40.064 (3)0.051 (2)0.0407 (19)0.011 (2)0.0036 (19)0.0070 (18)
C50.056 (2)0.049 (2)0.0438 (19)0.007 (2)0.0119 (19)0.0098 (17)
C60.039 (2)0.0334 (16)0.0414 (17)0.0030 (16)0.0034 (16)0.0017 (16)
N70.0406 (19)0.0458 (16)0.0425 (15)0.0007 (15)0.0052 (14)0.0095 (14)
C80.076 (3)0.045 (2)0.066 (3)0.011 (2)0.005 (2)0.015 (2)
C90.099 (4)0.046 (2)0.097 (3)0.011 (3)0.004 (3)0.021 (2)
C100.051 (3)0.060 (2)0.058 (2)0.012 (2)0.006 (2)0.010 (2)
C110.0288 (19)0.0297 (16)0.0316 (15)0.0013 (15)0.0019 (14)0.0035 (14)
C120.0230 (18)0.0348 (17)0.0413 (17)0.0034 (15)0.0018 (15)0.0006 (16)
C130.036 (2)0.0318 (17)0.0408 (17)0.0057 (16)0.0029 (16)0.0019 (16)
C140.0320 (19)0.0310 (17)0.0358 (16)0.0000 (15)0.0035 (15)0.0045 (15)
C150.0255 (18)0.0355 (17)0.0441 (17)0.0003 (16)0.0036 (15)0.0027 (16)
C160.0283 (19)0.0307 (17)0.0407 (17)0.0052 (15)0.0022 (15)0.0035 (15)
C170.047 (2)0.086 (3)0.036 (2)0.006 (2)0.0034 (19)0.005 (2)
C180.055 (3)0.147 (5)0.056 (2)0.006 (3)0.017 (2)0.016 (3)
O10.0466 (17)0.0480 (15)0.0671 (16)0.0003 (14)0.0241 (14)0.0041 (14)
O20.0383 (16)0.080 (2)0.096 (2)0.0216 (16)0.0010 (16)0.0242 (18)
O30.0569 (19)0.0639 (17)0.094 (2)0.0079 (16)0.0072 (16)0.0447 (17)
O40.0368 (17)0.0778 (19)0.094 (2)0.0062 (16)0.0110 (16)0.0304 (17)
O50.0602 (18)0.0344 (14)0.089 (2)0.0120 (13)0.0011 (16)0.0061 (14)
O60.0522 (18)0.075 (2)0.0832 (19)0.0180 (16)0.0279 (17)0.0056 (16)
O70.075 (2)0.0656 (19)0.0646 (16)0.0316 (17)0.0110 (16)0.0027 (15)
N20.0293 (17)0.0349 (16)0.0631 (19)0.0033 (13)0.0052 (16)0.0001 (15)
N30.0393 (19)0.0414 (16)0.0468 (17)0.0003 (16)0.0061 (15)0.0078 (15)
N40.0324 (18)0.0457 (18)0.0572 (18)0.0083 (15)0.0044 (16)0.0130 (17)
Geometric parameters (Å, º) top
N1—C111.371 (4)C10—H10A0.9700
N1—C51.469 (4)C10—H10B0.9700
N1—C21.479 (4)C11—C121.407 (4)
C2—C31.522 (4)C11—C161.422 (4)
C2—C61.538 (4)C12—C131.376 (5)
C2—H20.9800C12—N21.479 (4)
C3—C41.512 (5)C13—C141.361 (4)
C3—H3A0.9700C13—H130.9300
C3—H3B0.9700C14—C151.380 (4)
C4—C51.514 (5)C14—N31.471 (4)
C4—H4A0.9700C15—C161.362 (4)
C4—H4B0.9700C15—H150.9300
C5—H5A0.9700C16—N41.479 (4)
C5—H5B0.9700C17—O71.227 (5)
C6—N71.466 (4)C17—C181.504 (6)
C6—C101.527 (5)C18—H18A0.9600
C6—H60.9800C18—H18B0.9600
N7—C171.361 (5)C18—H18C0.9600
N7—C81.463 (4)O1—N21.213 (4)
C8—C91.497 (6)O2—N21.220 (4)
C8—H8A0.9700O3—N31.220 (4)
C8—H8B0.9700O4—N31.206 (4)
C9—C101.519 (6)O5—N41.216 (4)
C9—H9A0.9700O6—N41.217 (4)
C9—H9B0.9700
C11—N1—C5122.7 (3)C8—C9—H9B110.5
C11—N1—C2124.3 (2)C10—C9—H9B110.5
C5—N1—C2111.6 (2)H9A—C9—H9B108.7
N1—C2—C3102.8 (3)C9—C10—C6105.6 (3)
N1—C2—C6110.5 (3)C9—C10—H10A110.6
C3—C2—C6117.3 (3)C6—C10—H10A110.6
N1—C2—H2108.7C9—C10—H10B110.6
C3—C2—H2108.7C6—C10—H10B110.6
C6—C2—H2108.7H10A—C10—H10B108.7
C4—C3—C2103.2 (3)N1—C11—C12125.0 (3)
C4—C3—H3A111.1N1—C11—C16122.0 (3)
C2—C3—H3A111.1C12—C11—C16113.0 (3)
C4—C3—H3B111.1C13—C12—C11123.4 (3)
C2—C3—H3B111.1C13—C12—N2114.5 (3)
H3A—C3—H3B109.1C11—C12—N2121.5 (3)
C3—C4—C5103.0 (3)C14—C13—C12119.2 (3)
C3—C4—H4A111.2C14—C13—H13120.4
C5—C4—H4A111.2C12—C13—H13120.4
C3—C4—H4B111.2C13—C14—C15121.4 (3)
C5—C4—H4B111.2C13—C14—N3118.8 (3)
H4A—C4—H4B109.1C15—C14—N3119.7 (3)
N1—C5—C4102.5 (3)C16—C15—C14117.9 (3)
N1—C5—H5A111.3C16—C15—H15121.0
C4—C5—H5A111.3C14—C15—H15121.0
N1—C5—H5B111.3C15—C16—C11124.6 (3)
C4—C5—H5B111.3C15—C16—N4116.2 (3)
H5A—C5—H5B109.2C11—C16—N4119.1 (3)
N7—C6—C10103.9 (3)O7—C17—N7121.3 (4)
N7—C6—C2110.8 (3)O7—C17—C18122.6 (4)
C10—C6—C2115.8 (3)N7—C17—C18116.1 (4)
N7—C6—H6108.7C17—C18—H18A109.5
C10—C6—H6108.7C17—C18—H18B109.5
C2—C6—H6108.7H18A—C18—H18B109.5
C17—N7—C8124.8 (3)C17—C18—H18C109.5
C17—N7—C6119.9 (3)H18A—C18—H18C109.5
C8—N7—C6113.0 (3)H18B—C18—H18C109.5
N7—C8—C9104.2 (3)O1—N2—O2123.6 (3)
N7—C8—H8A110.9O1—N2—C12118.3 (3)
C9—C8—H8A110.9O2—N2—C12117.8 (3)
N7—C8—H8B110.9O4—N3—O3123.6 (3)
C9—C8—H8B110.9O4—N3—C14118.9 (3)
H8A—C8—H8B108.9O3—N3—C14117.5 (3)
C8—C9—C10106.0 (3)O5—N4—O6124.9 (3)
C8—C9—H9A110.5O5—N4—C16117.5 (3)
C10—C9—H9A110.5O6—N4—C16117.5 (3)
C11—N1—C2—C3175.5 (3)N1—C11—C12—N218.7 (5)
C5—N1—C2—C38.9 (3)C16—C11—C12—N2162.5 (3)
C11—N1—C2—C658.6 (4)C11—C12—C13—C144.3 (5)
C5—N1—C2—C6134.7 (3)N2—C12—C13—C14166.1 (3)
N1—C2—C3—C430.8 (3)C12—C13—C14—C152.0 (5)
C6—C2—C3—C4152.1 (3)C12—C13—C14—N3179.1 (3)
C2—C3—C4—C541.6 (4)C13—C14—C15—C164.4 (5)
C11—N1—C5—C4150.3 (3)N3—C14—C15—C16178.5 (3)
C2—N1—C5—C416.5 (4)C14—C15—C16—C110.9 (5)
C3—C4—C5—N135.4 (4)C14—C15—C16—N4175.7 (3)
N1—C2—C6—N7174.9 (2)N1—C11—C16—C15174.2 (3)
C3—C2—C6—N767.9 (4)C12—C11—C16—C154.6 (5)
N1—C2—C6—C1067.2 (4)N1—C11—C16—N42.3 (5)
C3—C2—C6—C1050.0 (4)C12—C11—C16—N4178.9 (3)
C10—C6—N7—C17160.1 (3)C8—N7—C17—O7170.4 (4)
C2—C6—N7—C1774.9 (4)C6—N7—C17—O78.8 (5)
C10—C6—N7—C83.5 (4)C8—N7—C17—C188.8 (5)
C2—C6—N7—C8121.4 (3)C6—N7—C17—C18170.5 (3)
C17—N7—C8—C9176.1 (3)C13—C12—N2—O1146.0 (3)
C6—N7—C8—C913.3 (4)C11—C12—N2—O124.5 (4)
N7—C8—C9—C1024.7 (4)C13—C12—N2—O228.0 (4)
C8—C9—C10—C627.4 (4)C11—C12—N2—O2161.5 (3)
N7—C6—C10—C918.8 (4)C13—C14—N3—O4174.7 (3)
C2—C6—C10—C9102.9 (4)C15—C14—N3—O42.5 (5)
C5—N1—C11—C12126.2 (3)C13—C14—N3—O35.9 (5)
C2—N1—C11—C1239.0 (4)C15—C14—N3—O3176.9 (3)
C5—N1—C11—C1655.2 (4)C15—C16—N4—O5114.2 (3)
C2—N1—C11—C16139.6 (3)C11—C16—N4—O562.5 (4)
N1—C11—C12—C13171.6 (3)C15—C16—N4—O664.1 (4)
C16—C11—C12—C137.2 (4)C11—C16—N4—O6119.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.982.182.891 (4)129
C5—H5B···O50.972.593.157 (5)118
C2—H2···O70.982.503.079 (4)118
C18—H18C···O2i0.962.513.454 (5)168
Symmetry code: (i) x+2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC16H19N5O7
Mr393.36
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)8.1989 (5), 10.4442 (6), 20.8877 (13)
V3)1788.63 (19)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.20 × 0.20 × 0.15
Data collection
DiffractometerOxford Diffraction Xcalibur Eos
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2012)
Tmin, Tmax0.990, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
7678, 1818, 1477
Rint0.040
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.090, 1.06
No. of reflections1818
No. of parameters254
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.16

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.982.182.891 (4)129
C18—H18C···O2i0.962.513.454 (5)168
Symmetry code: (i) x+2, y+1/2, z+3/2.
 

References

First citationAgilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
First citationBaggio, R., Remedi, M. V., Garland, M. T. & Bujan, E. I. (1997). J. Chem. Crystallogr. 27, 499–505.  CrossRef CAS
First citationButcher, R. J., Gilardi, R., Flippen-Anderson, J. L. & George, C. (1992). New J. Chem. 16, 679–692.  CAS
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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Volume 69| Part 1| January 2013| Pages o144-o145
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