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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 12| December 2015| Pages o917-o918
https://doi.org/10.1107/S2056989015020794

Crystal structure of ethyl 2-{2-[(1Z)-1-hy­dr­oxy-3-(4-nitro­phen­yl)-3-oxoprop-1-en-1-yl]phen­­oxy}acetate

Shaaban K. Mohamed,a,b Joel T. Mague,c Mehmet Akkurt,d Eman A. Ahmede and Mustafa R. Albayatif*

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, eDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com

Edited by P. McArdle, National University of Ireland, Ireland (Received 30 October 2015; accepted 2 November 2015; online 7 November 2015)

The title compound, C19H17NO7, crystallized in a ratio of about 6:4 of the two possible keto–enol forms. This was observed as disorder over the central C3H2O2 unit. The dihedral angle between the rings is 8.2 (2)°.The mol­ecules pack by C—H⋯O interactions in a layered fashion parallel to (-104).

CCDC reference: 1434730

Similar articles

1. Related literature

For the use of aryl­oxyphen­oxy compounds in various herbicidal applications, see: Zhu et al. (2006[Zhu, X. L., Zhang, L., Chen, Q., Wan, J. & Yang, G. F. (2006). J. Chem. Inf. Model. 46, 1819-1826.], 2009[Zhu, X. L., Ge-Fei, H., Zhan, C. G. & Yang, G. F. (2009). J. Chem. Inf. Model. 49, 1936-1943.]); Li (2004[Li, H. P. (2004). Pestic. Sci. Admin. 25, 28-32.]); Wang et al. (2004[Wang, H. Q., Liu, H. & Liu, Z. J. (2004). Chin. J. Org. Chem. 24, 1563-1568.]). For the synthesis of the title compund, see: Akkurt et al. (2015[Akkurt, M., Mague, J. T., Mohamed, S. K., Ahmed, E. A. & Albayati, M. R. (2015). Acta Cryst. E71, o70-o71.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C19H17NO7

  • Mr = 371.33

  • Monoclinic, P 21 /n

  • a = 4.7818 (10) Å

  • b = 16.260 (3) Å

  • c = 21.948 (5) Å

  • β = 95.933 (3)°

  • V = 1697.4 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 150 K

  • 0.24 × 0.08 × 0.03 mm

2.2. Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2014[Bruker (2014). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.60, Tmax = 1.00

  • 15039 measured reflections

  • 3952 independent reflections

  • 1800 reflections with I > 2σ(I)

  • Rint = 0.116

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.072

  • wR(F2) = 0.194

  • S = 1.00

  • 3952 reflections

  • 245 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C8—H8⋯O5 0.95 2.18 2.796 (4) 122
C16—H16A⋯O3i 0.99 2.35 3.295 (5) 160
O3—H3A⋯O4 0.86 1.69 2.435 (3) 144
O4—H4A⋯O3 0.86 1.62 2.435 (3) 158
Symmetry code: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2014[Bruker (2014). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2014[Bruker (2014). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

CCDC reference: 1434730

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015020794/qm2113sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015020794/qm2113Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015020794/qm2113Isup3.cml

checkCIF report


Comment top

Aryloxyphenoxy propionates are an important class of herbicides due to their high efficiency, broad spectrum, low toxicity and good selectivity (Zhu et al., 2006; Zhu et al., 2009). Thus, aryloxy-phenoxy propionate herbicides such as fluazifop-butyl, heloxyfop-methyl, quizalofop-ethyl and cyhalofop-butyl have been developed (Li, 2004), and are widely used to control gramineous weeds. In addition, some aryloxy-phenoxy acetates exhibit good herbicidal activity. For example, two substituted pyrazolo[3,4-d] pyrimidin-4-yloxy phenoxy acetates display considerable activities (Wang et al., 2004), with 100% inhibition against the root growth of Brassica napus L. Based on such facts, we report in this study the synthesis and crystal structural determination of the title compound.

In the title molecule, the dihedral angle between the C1–C6 ring and the mean plane of the central O3, C7, C8, C9, O4 unit is 2.8 (2)° while that between this latter plane and the C10–C15 ring is 8.2 (2)°. The molecule crystallized as a mixture of the two possible keto enol forms. This was observed as disorder over the central C3H2O2 unit. The molecules pack in a layered fashion (Figs. 2 and 3).

Related literature top

For the use of aryloxyphenoxy compounds in various herbicidal applications, see: Zhu et al. (2006, 2009); Li (2004); Wang et al. (2004). For the synthesis of the title compund, see: Akkurt et al. (2015).

Experimental top

The title compund was prepared according to our reported method (Akkurt et al., 2015). Suitable crystals were obtained by slow evaporation method of a solution of the title compund in ethanol.

Refinement top

H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. From the equivalence of the C7—C8 and C8—C9 bond distances, the near equivalence of the C7—O3 and C9—O4 bond distances and the observance of only one peak attributable to a hydrogen attached to C8 in a difference map, it was concluded that the compound exists as the keto-enol tautomer with the enol hydrogen disordered between O3 and O4. Contoured difference maps calculated in the region between O3 and O4 showed an elongated region of density consistent with this assumption. The two components of the disordered hydrogen (H3a and H4a) were placed in positions consistent with forming intramolecular O—H···O hydrogen bonds and allowed to ride on the respective oxygen atoms.

Structure description top

Aryloxyphenoxy propionates are an important class of herbicides due to their high efficiency, broad spectrum, low toxicity and good selectivity (Zhu et al., 2006; Zhu et al., 2009). Thus, aryloxy-phenoxy propionate herbicides such as fluazifop-butyl, heloxyfop-methyl, quizalofop-ethyl and cyhalofop-butyl have been developed (Li, 2004), and are widely used to control gramineous weeds. In addition, some aryloxy-phenoxy acetates exhibit good herbicidal activity. For example, two substituted pyrazolo[3,4-d] pyrimidin-4-yloxy phenoxy acetates display considerable activities (Wang et al., 2004), with 100% inhibition against the root growth of Brassica napus L. Based on such facts, we report in this study the synthesis and crystal structural determination of the title compound.

In the title molecule, the dihedral angle between the C1–C6 ring and the mean plane of the central O3, C7, C8, C9, O4 unit is 2.8 (2)° while that between this latter plane and the C10–C15 ring is 8.2 (2)°. The molecule crystallized as a mixture of the two possible keto enol forms. This was observed as disorder over the central C3H2O2 unit. The molecules pack in a layered fashion (Figs. 2 and 3).

For the use of aryloxyphenoxy compounds in various herbicidal applications, see: Zhu et al. (2006, 2009); Li (2004); Wang et al. (2004). For the synthesis of the title compund, see: Akkurt et al. (2015).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The title molecule with labeling scheme and 50% probability ellipsoids. Only one location (H4A) of the disordered enol hydrogen is shown. Intramolecular hydrogen bonds are shown by dotted lines.
[Figure 2] Fig. 2. Packing viewed down the a axis. Intermolecular C—H···O hydrogen bonds are shown by dotted lines.
[Figure 3] Fig. 3. Packing viewed down the b axis showing the layered structure.
Ethyl 2-{2-[(1Z)-1-hydroxy-3-(4-nitrophenyl)-3-oxoprop-1-en-1-yl]phenoxy}acetate top
Crystal data top
C19H17NO7F(000) = 776
Mr = 371.33Dx = 1.453 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 4.7818 (10) ÅCell parameters from 2496 reflections
b = 16.260 (3) Åθ = 2.3–26.7°
c = 21.948 (5) ŵ = 0.11 mm−1
β = 95.933 (3)°T = 150 K
V = 1697.4 (6) Å3Column, pale yellow
Z = 40.24 × 0.08 × 0.03 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		3952 independent reflections
Radiation source: fine-focus sealed tube1800 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.116
Detector resolution: 8.3660 pixels mm-1θmax = 27.9°, θmin = 1.6°
φ and ω scansh = −6→6
Absorption correction: multi-scan
(SADABS; Bruker, 2014)		k = −20→20
Tmin = 0.60, Tmax = 1.00l = −28→28
15039 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)] = 0.072Hydrogen site location: mixed
wR(F2) = 0.194H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0701P)2 + 0.4312P]
where P = (Fo2 + 2Fc2)/3
3952 reflections(Δ/σ)max < 0.001
245 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
Crystal data top
C19H17NO7V = 1697.4 (6) Å3
Mr = 371.33Z = 4
Monoclinic, P21/nMo Kα radiation
a = 4.7818 (10) ŵ = 0.11 mm−1
b = 16.260 (3) ÅT = 150 K
c = 21.948 (5) Å0.24 × 0.08 × 0.03 mm
β = 95.933 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer		3952 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2014)		1800 reflections with I > 2σ(I)
Tmin = 0.60, Tmax = 1.00Rint = 0.116
15039 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0720 restraints
wR(F2) = 0.194H-atom parameters constrained
S = 1.00Δρmax = 0.23 e Å−3
3952 reflectionsΔρmin = −0.29 e Å−3
245 parameters
Special details top

Experimental. The diffraction data were collected in three sets of 363 frames (0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 120 sec/frame was used.

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. From the equivalence of the C7—C8 and C8—C9 bond distances, the near equivalence of the C7—O3 and C9—O4 bond distances and the observance of only one peak attributable to a hydrogen attached to C8 in a difference map, it was concluded that the compound exists as the keto-enol tautomer with the enol hydrogen disordered between O3 and O4. Contoured difference maps calculated in the region between O3 and O4 showed an elongated region of density consistent with this assumption. The two components of the disordered hydrogen (H3a and H4a) were placed in positions consistent with forming intramolecular O—H···O hydrogen bonds and allowed to ride on the respective oxygen atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O11.3713 (6)0.88831 (19)0.52969 (13)0.0660 (9)
O21.3341 (6)0.75575 (19)0.52420 (12)0.0568 (8)
O30.2970 (5)0.93367 (15)0.30167 (11)0.0469 (7)
H3A0.15390.93680.27460.070*0.4
O4−0.0854 (5)0.88128 (16)0.23034 (12)0.0559 (8)
H4A0.05130.90930.24850.084*0.6
O5−0.0494 (5)0.63587 (13)0.28606 (10)0.0391 (6)
O60.3347 (6)0.58820 (15)0.37708 (13)0.0575 (8)
O70.1989 (6)0.45723 (15)0.36325 (12)0.0539 (8)
N11.2619 (7)0.8252 (2)0.50788 (14)0.0482 (9)
C10.5850 (7)0.8492 (2)0.36892 (15)0.0324 (8)
C20.7260 (7)0.9186 (2)0.39276 (17)0.0412 (9)
H20.67030.97150.37750.049*
C30.9464 (8)0.9116 (2)0.43836 (17)0.0451 (10)
H31.04100.95910.45510.054*
C41.0263 (7)0.8345 (2)0.45906 (15)0.0368 (9)
C50.8938 (7)0.7638 (2)0.43615 (16)0.0398 (9)
H50.95350.71120.45100.048*
C60.6703 (7)0.7720 (2)0.39061 (15)0.0372 (9)
H60.57530.72440.37420.045*
C70.3471 (7)0.8596 (2)0.31935 (15)0.0321 (8)
C80.1895 (7)0.7929 (2)0.29482 (15)0.0329 (8)
H80.23330.73880.30910.039*
C9−0.0329 (7)0.8058 (2)0.24920 (15)0.0331 (8)
C10−0.2205 (7)0.7428 (2)0.21933 (15)0.0327 (8)
C11−0.4082 (7)0.7682 (2)0.16947 (15)0.0384 (9)
H11−0.40630.82410.15680.046*
C12−0.5941 (7)0.7148 (2)0.13854 (16)0.0440 (10)
H12−0.71850.73390.10490.053*
C13−0.6003 (8)0.6340 (2)0.15610 (16)0.0448 (10)
H13−0.72870.59690.13470.054*
C14−0.4184 (8)0.6064 (2)0.20538 (16)0.0437 (10)
H14−0.42330.55050.21770.052*
C15−0.2297 (7)0.6604 (2)0.23651 (15)0.0353 (8)
C16−0.0496 (8)0.5517 (2)0.30174 (16)0.0397 (9)
H16A−0.01990.51760.26560.048*
H16B−0.23240.53630.31600.048*
C170.1850 (8)0.5374 (2)0.35214 (16)0.0384 (9)
C180.4091 (8)0.4278 (2)0.41157 (17)0.0489 (10)
H18A0.56340.46830.41860.059*
H18B0.48990.37510.39900.059*
C190.2724 (9)0.4159 (3)0.46874 (18)0.0589 (12)
H19A0.19490.46830.48120.088*
H19B0.41170.39590.50130.088*
H19C0.12050.37550.46150.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0585 (19)0.076 (2)0.0572 (19)−0.0132 (17)−0.0234 (15)−0.0046 (17)
O20.0511 (18)0.073 (2)0.0420 (16)0.0133 (15)−0.0162 (13)0.0053 (15)
O30.0465 (15)0.0384 (15)0.0514 (17)−0.0023 (12)−0.0164 (13)0.0115 (12)
O40.0570 (18)0.0470 (17)0.0582 (18)−0.0019 (14)−0.0211 (14)0.0137 (14)
O50.0443 (15)0.0320 (14)0.0364 (14)0.0022 (11)−0.0179 (12)0.0032 (11)
O60.0611 (18)0.0403 (16)0.0629 (19)−0.0073 (14)−0.0321 (15)0.0070 (14)
O70.0628 (18)0.0381 (16)0.0534 (17)0.0016 (13)−0.0295 (14)0.0066 (13)
N10.0387 (19)0.073 (3)0.0314 (18)−0.0048 (19)−0.0042 (15)−0.0007 (18)
C10.0299 (18)0.037 (2)0.0298 (18)0.0020 (16)−0.0013 (15)0.0016 (16)
C20.039 (2)0.041 (2)0.042 (2)0.0028 (17)−0.0036 (18)0.0011 (17)
C30.044 (2)0.047 (3)0.042 (2)−0.0021 (19)−0.0090 (18)−0.0069 (19)
C40.0300 (19)0.053 (2)0.0271 (19)0.0017 (17)0.0007 (15)−0.0004 (17)
C50.036 (2)0.045 (2)0.037 (2)0.0052 (17)−0.0063 (17)0.0045 (18)
C60.037 (2)0.039 (2)0.035 (2)−0.0024 (16)−0.0027 (16)0.0030 (17)
C70.0322 (19)0.034 (2)0.0304 (19)0.0040 (16)0.0028 (16)0.0043 (16)
C80.0305 (19)0.036 (2)0.0309 (19)0.0050 (15)−0.0027 (15)0.0032 (15)
C90.0340 (19)0.035 (2)0.0303 (19)0.0039 (16)0.0014 (16)0.0063 (16)
C100.0294 (19)0.040 (2)0.0269 (18)0.0037 (15)−0.0052 (14)−0.0012 (15)
C110.0312 (19)0.046 (2)0.035 (2)0.0057 (17)−0.0073 (16)0.0066 (17)
C120.037 (2)0.058 (3)0.034 (2)0.0027 (19)−0.0115 (17)0.0007 (19)
C130.043 (2)0.051 (3)0.037 (2)−0.0009 (19)−0.0102 (18)−0.0066 (19)
C140.047 (2)0.042 (2)0.039 (2)0.0005 (18)−0.0119 (18)0.0003 (18)
C150.0322 (19)0.045 (2)0.0265 (18)0.0078 (17)−0.0056 (15)−0.0019 (17)
C160.040 (2)0.036 (2)0.039 (2)0.0007 (17)−0.0130 (17)0.0023 (17)
C170.045 (2)0.030 (2)0.037 (2)0.0020 (17)−0.0077 (18)0.0056 (17)
C180.052 (2)0.048 (2)0.043 (2)0.006 (2)−0.0136 (19)0.0080 (19)
C190.057 (3)0.068 (3)0.048 (3)0.007 (2)−0.013 (2)0.000 (2)
Geometric parameters (Å, º) top
O1—N11.226 (4)C7—C81.396 (5)
O2—N11.224 (4)C8—C91.399 (4)
O3—C71.281 (4)C8—H80.9500
O3—H3A0.8600C9—C101.470 (5)
O4—C91.311 (4)C10—C151.394 (5)
O4—H4A0.8601C10—C111.404 (4)
O5—C151.375 (4)C11—C121.371 (5)
O5—C161.412 (4)C11—H110.9500
O6—C171.189 (4)C12—C131.371 (5)
O7—C171.327 (4)C12—H120.9500
O7—C181.464 (4)C13—C141.390 (5)
N1—C41.480 (4)C13—H130.9500
C1—C61.388 (4)C14—C151.387 (5)
C1—C21.390 (5)C14—H140.9500
C1—C71.500 (5)C16—C171.510 (5)
C2—C31.381 (5)C16—H16A0.9900
C2—H20.9500C16—H16B0.9900
C3—C41.374 (5)C18—C191.486 (5)
C3—H30.9500C18—H18A0.9900
C4—C51.381 (5)C18—H18B0.9900
C5—C61.392 (5)C19—H19A0.9800
C5—H50.9500C19—H19B0.9800
C6—H60.9500C19—H19C0.9800
C7—O3—H3A112.1C12—C11—C10122.0 (3)
C9—O4—H4A103.8C12—C11—H11119.0
C15—O5—C16117.3 (3)C10—C11—H11119.0
C17—O7—C18118.2 (3)C13—C12—C11120.0 (3)
O2—N1—O1124.2 (3)C13—C12—H12120.0
O2—N1—C4118.4 (3)C11—C12—H12120.0
O1—N1—C4117.4 (3)C12—C13—C14119.9 (3)
C6—C1—C2119.4 (3)C12—C13—H13120.1
C6—C1—C7121.6 (3)C14—C13—H13120.1
C2—C1—C7118.9 (3)C15—C14—C13120.1 (4)
C3—C2—C1120.6 (3)C15—C14—H14120.0
C3—C2—H2119.7C13—C14—H14120.0
C1—C2—H2119.7O5—C15—C14121.9 (3)
C4—C3—C2118.7 (3)O5—C15—C10117.3 (3)
C4—C3—H3120.6C14—C15—C10120.8 (3)
C2—C3—H3120.6O5—C16—C17108.0 (3)
C3—C4—C5122.5 (3)O5—C16—H16A110.1
C3—C4—N1119.8 (3)C17—C16—H16A110.1
C5—C4—N1117.7 (3)O5—C16—H16B110.1
C4—C5—C6118.1 (3)C17—C16—H16B110.1
C4—C5—H5121.0H16A—C16—H16B108.4
C6—C5—H5121.0O6—C17—O7125.6 (3)
C1—C6—C5120.6 (3)O6—C17—C16126.7 (3)
C1—C6—H6119.7O7—C17—C16107.7 (3)
C5—C6—H6119.7O7—C18—C19109.0 (3)
O3—C7—C8122.5 (3)O7—C18—H18A109.9
O3—C7—C1115.5 (3)C19—C18—H18A109.9
C8—C7—C1122.1 (3)O7—C18—H18B109.9
C7—C8—C9120.0 (3)C19—C18—H18B109.9
C7—C8—H8120.0H18A—C18—H18B108.3
C9—C8—H8120.0C18—C19—H19A109.5
O4—C9—C8118.2 (3)C18—C19—H19B109.5
O4—C9—C10115.0 (3)H19A—C19—H19B109.5
C8—C9—C10126.8 (3)C18—C19—H19C109.5
C15—C10—C11117.2 (3)H19A—C19—H19C109.5
C15—C10—C9125.7 (3)H19B—C19—H19C109.5
C11—C10—C9117.0 (3)
C6—C1—C2—C3−1.1 (5)C8—C9—C10—C158.1 (6)
C7—C1—C2—C3−179.9 (3)O4—C9—C10—C117.8 (5)
C1—C2—C3—C41.0 (6)C8—C9—C10—C11−172.5 (3)
C2—C3—C4—C5−0.2 (6)C15—C10—C11—C120.0 (5)
C2—C3—C4—N1180.0 (3)C9—C10—C11—C12−179.5 (3)
O2—N1—C4—C3−177.9 (3)C10—C11—C12—C130.0 (6)
O1—N1—C4—C32.6 (5)C11—C12—C13—C140.1 (6)
O2—N1—C4—C52.3 (5)C12—C13—C14—C15−0.4 (6)
O1—N1—C4—C5−177.2 (3)C16—O5—C15—C144.2 (5)
C3—C4—C5—C6−0.4 (6)C16—O5—C15—C10−177.2 (3)
N1—C4—C5—C6179.4 (3)C13—C14—C15—O5178.9 (3)
C2—C1—C6—C50.5 (5)C13—C14—C15—C100.4 (6)
C7—C1—C6—C5179.2 (3)C11—C10—C15—O5−178.8 (3)
C4—C5—C6—C10.2 (5)C9—C10—C15—O50.6 (5)
C6—C1—C7—O3−177.2 (3)C11—C10—C15—C14−0.3 (5)
C2—C1—C7—O31.6 (5)C9—C10—C15—C14179.2 (3)
C6—C1—C7—C83.6 (5)C15—O5—C16—C17173.6 (3)
C2—C1—C7—C8−177.7 (3)C18—O7—C17—O62.1 (6)
O3—C7—C8—C9−0.1 (5)C18—O7—C17—C16−178.9 (3)
C1—C7—C8—C9179.1 (3)O5—C16—C17—O64.0 (6)
C7—C8—C9—O40.5 (5)O5—C16—C17—O7−175.0 (3)
C7—C8—C9—C10−179.2 (3)C17—O7—C18—C1997.7 (4)
O4—C9—C10—C15−171.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O50.952.182.796 (4)122
C16—H16A···O3i0.992.353.295 (5)160
O3—H3A···O40.861.692.435 (3)144
O4—H4A···O30.861.622.435 (3)158
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O50.952.182.796 (4)122
C16—H16A···O3i0.992.353.295 (5)160
O3—H3A···O40.861.692.435 (3)144
O4—H4A···O30.861.622.435 (3)158
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.
 

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

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ISSN: 2056-9890
Volume 71| Part 12| December 2015| Pages o917-o918
https://doi.org/10.1107/S2056989015020794
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