organic papers
Acta Cryst.(2006). E62, o735–o736 doi:10.1107/S1600536806002194 Minet al. C
21H18FN3O5H2O
o735
Acta Crystallographica Section EStructure Reports
Online
ISSN 1600-5368
2-(1,3-Dioxo-4,5,6,7-tetrahydro-1
H
-isoindol-2-yl)-
N
-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2
H
-benzoxazin-6-yl]-acetamide monohydrate
Zhong-Cheng Min,aMing-Zhi Huang,b* Wei-Min Chen,aQuan Zhangaand Guang-Fu Yanga aKey Laboratory of Pesticides and Chemical
Biology, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, People’s Republic of China, andbHunan
Research Institute of Chemical Industry, Changsha 410007, People’s Republic of China
Correspondence e-mail: jacobmin@163.com
Key indicators
Single-crystal X-ray study
T= 292 K
Mean(C–C) = 0.004 A˚ Disorder in main residue
Rfactor = 0.062
wRfactor = 0.167
Data-to-parameter ratio = 11.3
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 14 December 2005 Accepted 18 January 2006
#2006 International Union of Crystallography All rights reserved
In the title compound, C21H18FN3O5H2O, the cyclohexene
ring exhibits a distorted chair conformation. The crystal packing is stabilized by intra- and intermolecular hydrogen bonds.
Comment
Herbicides inhibiting protoporphyrinogen oxidase (protox) have been sold commercially for nearly 40 years (Dayan & Duke, 1997). The title compound, (I), may belong to this family of protox-inhibiting herbicides and we present its crystal structure here.
The molecular stucture of (I) is shown in Fig. 1. The C10— N2 bond is shorter than the normal value of C—N [1.47 (2) A˚ ; Sasada, 1984]. The bond length of C2—C3 is slightly greater than the normal value of C–C [1.54 (3) A˚ ; Sasada, 1984]. The torsion angles C1—C2—C3—C4 and C2—C3—C4—C5 indi-cate a distorted chair conformation of the cyclohexene ring. The sum of the C8—N1—C7, C8—N1—C9 and C7—N1—C9 angles is 359.9, the sum of the C10—N2—C11, C10—N2—H2
and C11—N2—H2 angles is 359.1and the sum of the C17—
[image:1.610.224.440.314.401.2] [image:1.610.209.457.551.725.2]N3—C15, C17—N3—C19 and C15—N3—C19 angles is 360.0.
Figure 1
Therefore, atoms N1, N2 and N3 are sp2 hybridized. The molecules of (I) form two-dimensional layers through hydrogen bonds in theacplane (Table 2 and Fig. 2).
Experimental
2-[1,3-Dioxo-4,5,6,7-tetrahydro-1H-isoindol-2-yl]acetyl choride (1.2 mmol) in dry toluene (10 ml) was added dropwise to a solution of 6-amino-7-fluoro-4-(prop-2-ynyl)-2H-benzoxazin-3(4H)-one (1 mmol) and triethylamine (1.2 mmol) in dry toluene (10 ml) under N2at
room temperature, and the resulting mixture was stirred for 2 h. After filtration, the solid was washed with water and recrystallized from petroleum ether and methanol (4:1 v/v). Colorless plate-shaped crystals of (I) were obtained by evaporation of the solvent over a period of two weeks.
Crystal data
C21H18FN3O5H2O
Mr= 429.40 Monoclinic,P21=n a= 19.2192 (19) A˚ b= 4.7354 (5) A˚ c= 23.421 (2) A˚ = 92.091 (2) V= 2130.2 (4) A˚3 Z= 4
Dx= 1.339 Mg m
3
MoKradiation Cell parameters from 2160
reflections = 2.7–21.4
= 0.11 mm1 T= 292 (2) K Plate, colorless 0.400.100.02 mm
Data collection
Bruker SMART CCD area-detector diffractometer
’and!scans
Absorption correction: multi-scan (SADABS; Bruker, 2000) Tmin= 0.959,Tmax= 0.998
14145 measured reflections
3719 independent reflections 2411 reflections withI> 2(I) Rint= 0.050
max= 25.0
h=21!22 k=5!5 l=27!27
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.062 wR(F2) = 0.167
S= 1.04 3719 reflections 328 parameters
H atoms treated by a mixture of independent and constrained
w= 1/[2(F
o2) + (0.0734P)2
+ 0.5971P]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001 max= 0.26 e A˚
3
min=0.21 e A˚
3
Table 1
Selected geometric parameters (A˚ ,).
C2—C3 1.560 (7) C10—N2 1.318 (4)
C8—N1—C7 109.7 (2)
C8—N1—C9 126.7 (3)
C7—N1—C9 123.5 (3)
C10—N2—C11 126.1 (2)
C17—N3—C15 120.9 (3)
C17—N3—C19 118.9 (2)
C15—N3—C19 120.2 (2)
[image:2.610.47.294.70.247.2]C1—C2—C3—C4 31.5 (10) C2—C3—C4—C5 52.1 (12)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
C21—H21 O2i
0.93 2.33 3.244 (5) 168
C19—H19B O4 0.97 2.30 2.735 (4) 106
C13—H13 O1ii
0.93 2.44 3.354 (4) 170
C9—H9A O3iii
0.97 2.48 3.189 (8) 130
C4—H4B O4iv
0.97 2.54 3.454 (8) 157
N2—H2 O3iii
0.851 (10) 2.04 (2) 2.847 (9) 158 (3)
Symmetry codes: (i)xþ1;y;z; (ii) xþ1 2;y
1 2;zþ
1
2; (iii) x;y1;z; (iv) xþ1
2;yþ 3 2;zþ
1 2.
The amide and water H atoms were located in a difference map and were refined with the restraints N—H = 0.86 (1) A˚ and O—H = 0.82 A˚ , and withUiso(H) = 1.2Ueq(carrier) for H1 and 1.5Ueq(carrier)
for water H atoms. Other H atoms were positioned geometrically, with C—H = 0.93 or 0.97 A˚ , and refined in a riding model, with
Uiso(H)= 1.2Ueq(C) or 1.5Ueq(methyl C). Two of the C atoms in the
cyclohexene ring were disordered over two positions, and the occu-pancy factors for disordered positions C3/C30 and C4/C40 were
refined to 0.709 (12) and 0.291 (12). Atom O3/O30 was disordered
over two positions, with occupancies of 0.77 (9) and 0.23 (9). Water atoms O6 and O60, with partial occupancies of 0.50 [initially refined to
0.504 (1)], were assigned tentatively, based only on the crystal-lographic evidence; the water probably derives from the methanol solvent used for recrystallization.
Data collection:SMART(Bruker, 2000); cell refinement:SAINT
(Bruker, 2000); data reduction:SAINT; program(s) used to solve structure:SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
SHELXTL (Bruker, 1997); software used to prepare material for publication:SHELXTL.
The authors acknowledge financial support from the National Natural Science Foundation of China (No. 20372021) and Hunan Province Natural Science Foundation of China (No. 03 JJY3018).
References
Bruker (1997). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2000).SMART(Version 5.059),SAINT(Version 6.01) andSADABS (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.
Dayan, F. E. & Duke, S. O. (1997).Brighton Crop Prot. Conf. Weeds,1, 83–92. Sasada, Y. (1984).Molecular and Crystal Structure in Chemistry Handbook,
3rd ed. The Chemical Society of Japan, Tokyo: Maruzen Press.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
Figure 2
[image:2.610.315.564.236.310.2]supporting information
sup-1 Acta Cryst. (2006). E62, o735–o736
supporting information
Acta Cryst. (2006). E62, o735–o736 [https://doi.org/10.1107/S1600536806002194]
2-(1,3-Dioxo-4,5,6,7-tetrahydro-1
H
-isoindol-2-yl)-
N
-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2
H
-benzoxazin-6-yl]acetamide monohydrate
Zhong-Cheng Min, Ming-Zhi Huang, Wei-Min Chen, Quan Zhang and Guang-Fu Yang
2-(1,3-Dioxo-2,3,4,5,6,7-hexahydro-1H-isoindol-2-yl)-N-[7-fluoro-3-oxo- 4-(prop-2-ynyl)-3,4-dihydro-2H
-benzoxazin-6-yl]acetamide monohydrate
Crystal data
C21H18FN3O5·H2O
Mr = 429.40
Monoclinic, P21/n
Hall symbol: -P2yn
a = 19.2192 (19) Å
b = 4.7354 (5) Å
c = 23.421 (2) Å
β = 92.091 (2)°
V = 2130.2 (4) Å3
Z = 4
F(000) = 896
Dx = 1.339 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 2160 reflections
θ = 2.7–21.4°
µ = 0.11 mm−1
T = 292 K Plate, colorless 0.40 × 0.10 × 0.02 mm
Data collection
Bruker SMART CCD area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ and ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2000)
Tmin = 0.959, Tmax = 0.998
14145 measured reflections 3719 independent reflections 2411 reflections with I > 2σ(I)
Rint = 0.050
θmax = 25.0°, θmin = 2.8°
h = −21→22
k = −5→5
l = −27→27
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.062
wR(F2) = 0.167
S = 1.04 3719 reflections 328 parameters 15 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.0734P)2 + 0.5971P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.26 e Å−3
Special details
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)
x y z Uiso*/Ueq Occ. (<1)
C1 0.60720 (14) 0.3328 (6) 0.25928 (13) 0.0468 (7) C2 0.67121 (16) 0.5108 (7) 0.26634 (16) 0.0746 (10)
H2A 0.6689 0.6674 0.2396 0.090* 0.709 (12) H2B 0.7121 0.3992 0.2587 0.090* 0.709 (12) H2C 0.6601 0.7070 0.2583 0.090* 0.291 (12) H2D 0.7062 0.4495 0.2402 0.090* 0.291 (12) C3 0.6759 (5) 0.6245 (16) 0.3289 (3) 0.105 (3) 0.709 (12) H3A 0.7246 0.6607 0.3386 0.126* 0.709 (12) H3B 0.6521 0.8050 0.3293 0.126* 0.709 (12) C4 0.6479 (3) 0.449 (2) 0.3748 (3) 0.108 (3) 0.709 (12) H4A 0.6771 0.2834 0.3804 0.130* 0.709 (12) H4B 0.6494 0.5557 0.4102 0.130* 0.709 (12) C3′ 0.6984 (6) 0.488 (4) 0.3266 (4) 0.075 (5)* 0.291 (12) H3C 0.7375 0.6136 0.3338 0.090* 0.291 (12) H3D 0.7125 0.2959 0.3357 0.090* 0.291 (12) C4′ 0.6357 (6) 0.576 (3) 0.3607 (8) 0.072 (5)* 0.291 (12) H4C 0.6173 0.7515 0.3448 0.087* 0.291 (12) H4D 0.6515 0.6144 0.3998 0.087* 0.291 (12) C5 0.57636 (19) 0.3595 (8) 0.36171 (14) 0.0771 (11)
H5A 0.5450 0.5147 0.3691 0.093* 0.709 (12) H5B 0.5647 0.2044 0.3867 0.093* 0.709 (12) H5C 0.5893 0.2029 0.3866 0.093* 0.291 (12) H5D 0.5342 0.4456 0.3752 0.093* 0.291 (12) C6 0.56631 (15) 0.2680 (6) 0.30106 (12) 0.0500 (7)
supporting information
sup-3 Acta Cryst. (2006). E62, o735–o736
C15 0.20908 (14) 0.1585 (5) 0.07990 (11) 0.0403 (7) C16 0.27669 (14) 0.0991 (6) 0.09790 (11) 0.0432 (7) H16 0.3133 0.1902 0.0806 0.052* C17 0.12532 (17) 0.4154 (7) 0.02037 (14) 0.0600 (9) C18 0.07094 (19) 0.2847 (10) 0.05558 (18) 0.0912 (13) H18A 0.0533 0.4312 0.0801 0.109* H18B 0.0328 0.2285 0.0298 0.109* C19 0.24822 (16) 0.4908 (6) 0.00510 (13) 0.0567 (8) H19A 0.2806 0.5739 0.0330 0.068* H19B 0.2283 0.6429 −0.0179 0.068* C20 0.28642 (18) 0.3003 (8) −0.03184 (14) 0.0655 (9) C21 0.3179 (2) 0.1523 (11) −0.06122 (17) 0.0949 (14) H21 0.3430 0.0343 −0.0846 0.114* F1 0.24981 (10) −0.4117 (4) 0.20857 (8) 0.0765 (6) N1 0.52498 (12) 0.0312 (5) 0.22077 (10) 0.0502 (6) N2 0.36005 (13) −0.1729 (5) 0.15766 (11) 0.0516 (7) H2 0.3664 (15) −0.347 (3) 0.1656 (12) 0.062* N3 0.19275 (12) 0.3509 (5) 0.03497 (9) 0.0459 (6) O1 0.46553 (13) −0.0447 (6) 0.30249 (11) 0.0838 (8) O2 0.60517 (13) 0.2019 (6) 0.15932 (10) 0.0845 (8)
O3 0.4102 (10) 0.2615 (12) 0.1619 (18) 0.072 (5) 0.77 (9) O3′ 0.399 (2) 0.255 (5) 0.185 (3) 0.052 (7) 0.23 (9) O4 0.10951 (12) 0.5820 (6) −0.01787 (10) 0.0842 (8)
O5 0.08732 (11) 0.0605 (6) 0.08892 (11) 0.0811 (8)
O6 0.494 (3) 0.865 (8) 0.006 (3) 0.43 (3) 0.50 H6A 0.506 (3) 0.951 (13) 0.035 (2) 0.038 (15)* 0.50 H6B 0.505 (9) 0.693 (9) 0.012 (6) 0.16 (7)* 0.50 O6′ 0.494 (7) 0.595 (14) −0.013 (4) 0.52 (4) 0.50 H6C 0.494 (7) 0.768 (16) −0.009 (4) 0.13 (5)* 0.50 H6D 0.474 (3) 0.555 (12) −0.044 (3) 0.053 (17)* 0.50
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C15 0.0465 (17) 0.0355 (15) 0.0387 (14) 0.0039 (13) −0.0032 (12) −0.0049 (12) C16 0.0454 (16) 0.0353 (15) 0.0487 (16) 0.0017 (13) −0.0030 (13) −0.0010 (13) C17 0.058 (2) 0.066 (2) 0.0555 (18) 0.0195 (17) −0.0087 (16) −0.0018 (17) C18 0.054 (2) 0.110 (3) 0.109 (3) 0.011 (2) −0.007 (2) 0.040 (3) C19 0.065 (2) 0.0487 (18) 0.0556 (18) 0.0039 (16) −0.0048 (15) 0.0114 (15) C20 0.056 (2) 0.092 (3) 0.0485 (18) −0.005 (2) 0.0015 (16) 0.0023 (19) C21 0.070 (3) 0.142 (4) 0.074 (3) 0.000 (3) 0.016 (2) −0.030 (3) F1 0.0923 (14) 0.0653 (12) 0.0711 (12) 0.0014 (11) −0.0058 (10) 0.0286 (10) N1 0.0454 (14) 0.0487 (15) 0.0555 (15) −0.0022 (12) −0.0105 (11) −0.0043 (12) N2 0.0545 (15) 0.0249 (12) 0.0735 (17) 0.0035 (12) −0.0220 (13) −0.0014 (12) N3 0.0460 (14) 0.0488 (14) 0.0427 (13) 0.0082 (12) −0.0027 (11) 0.0033 (11) O1 0.0685 (16) 0.0853 (18) 0.0989 (18) −0.0103 (14) 0.0203 (14) 0.0121 (15) O2 0.0893 (18) 0.105 (2) 0.0607 (15) −0.0030 (15) 0.0210 (13) −0.0088 (14) O3 0.061 (4) 0.030 (2) 0.123 (13) 0.0031 (19) −0.026 (6) −0.006 (3) O3′ 0.056 (11) 0.022 (6) 0.076 (17) 0.002 (6) −0.014 (10) 0.006 (10) O4 0.0785 (16) 0.0990 (19) 0.0738 (15) 0.0275 (15) −0.0135 (13) 0.0295 (14) O5 0.0439 (13) 0.104 (2) 0.0955 (17) 0.0057 (13) −0.0011 (12) 0.0277 (16) O6 0.34 (3) 0.45 (11) 0.49 (5) −0.05 (8) −0.28 (3) −0.02 (9) O6′ 0.60 (5) 0.40 (9) 0.54 (8) −0.10 (7) −0.39 (6) −0.03 (6)
Geometric parameters (Å, º)
supporting information
sup-5 Acta Cryst. (2006). E62, o735–o736
C6—C7 1.490 (4) N2—H2 0.851 (10) C7—O1 1.208 (3) O6—O6i 1.33 (8)
C7—N1 1.385 (4) O6—H6A 0.822 (11) C8—O2 1.207 (3) O6—H6B 0.846 (11) C8—N1 1.377 (4) O6—H6C 0.58 (8) C9—N1 1.436 (4) O6′—O6′ii 1.11 (9)
C9—C10 1.512 (4) O6′—H6B 0.77 (13) C9—H9A 0.9700 O6′—H6C 0.824 (11) C9—H9B 0.9700 O6′—H6D 0.830 (11) C10—O3 1.248 (5)
C4′—C3′—H3D 111.2 O5—C18—H18B 107.4 H3C—C3′—H3D 109.1 C17—C18—H18B 107.4 C3′—C4′—C5 115.1 (11) H18A—C18—H18B 107.0 C3′—C4′—H4C 108.5 N3—C19—C20 113.3 (3) C5—C4′—H4C 108.5 N3—C19—H19A 108.9 C3′—C4′—H4D 108.5 C20—C19—H19A 108.9 C5—C4′—H4D 108.5 N3—C19—H19B 108.9 H4C—C4′—H4D 107.5 C20—C19—H19B 108.9 C4—C5—C6 111.9 (4) H19A—C19—H19B 107.7 C6—C5—C4′ 104.5 (7) C21—C20—C19 178.7 (4) C4—C5—H5A 109.2 C20—C21—H21 180.0 C6—C5—H5A 109.2 C8—N1—C7 109.7 (2) C4′—C5—H5A 87.8 C8—N1—C9 126.7 (3) C4—C5—H5B 109.2 C7—N1—C9 123.5 (3) C6—C5—H5B 109.2 C10—N2—C11 126.1 (2) C4′—C5—H5B 134.7 C10—N2—H2 117 (2) H5A—C5—H5B 107.9 C11—N2—H2 116 (2) C4—C5—H5C 82.9 C17—N3—C15 120.9 (3) C6—C5—H5C 111.8 C17—N3—C19 118.9 (2) C4′—C5—H5C 110.2 C15—N3—C19 120.2 (2) H5A—C5—H5C 128.3 C18—O5—C14 118.6 (3) C4—C5—H5D 126.9 O6i—O6—H6A 70 (5)
C6—C5—H5D 110.6 O6i—O6—H6B 157 (10)
C4′—C5—H5D 110.7 H6A—O6—H6B 107.0 (19) H5B—C5—H5D 84.7 O6i—O6—H6C 128 (10)
H5C—C5—H5D 109.0 H6A—O6—H6C 154 (10) C1—C6—C7 107.9 (3) H6B—O6—H6C 48 (10) C1—C6—C5 125.6 (3) O6′ii—O6′—H6B 92 (10)
C7—C6—C5 126.4 (3) O6′ii—O6′—H6C 138 (10)
O1—C7—N1 124.2 (3) H6B—O6′—H6C 47 (10) O1—C7—C6 129.2 (3) O6′ii—O6′—H6D 112 (10)
N1—C7—C6 106.6 (3) H6B—O6′—H6D 154 (10) O2—C8—N1 125.0 (3) H6C—O6′—H6D 108.8 (19)
supporting information
sup-7 Acta Cryst. (2006). E62, o735–o736
C8—C1—C6—C7 1.2 (3) C1—C8—N1—C9 178.2 (2) C2—C1—C6—C7 −175.8 (3) O1—C7—N1—C8 −178.9 (3) C8—C1—C6—C5 177.2 (3) C6—C7—N1—C8 −1.5 (3) C2—C1—C6—C5 0.1 (5) O1—C7—N1—C9 5.0 (4) C4—C5—C6—C1 −19.3 (6) C6—C7—N1—C9 −177.6 (2) C4′—C5—C6—C1 8.9 (8) C10—C9—N1—C8 −104.5 (3) C4—C5—C6—C7 155.9 (5) C10—C9—N1—C7 70.9 (4) C4′—C5—C6—C7 −175.9 (7) O3—C10—N2—C11 −7 (3) C1—C6—C7—O1 177.4 (3) O3′—C10—N2—C11 24 (3) C5—C6—C7—O1 1.5 (5) C9—C10—N2—C11 −177.2 (3) C1—C6—C7—N1 0.1 (3) C12—C11—N2—C10 −134.2 (3) C5—C6—C7—N1 −175.8 (3) C16—C11—N2—C10 49.3 (4) C6—C1—C8—O2 179.1 (3) O4—C17—N3—C15 179.4 (3) C2—C1—C8—O2 −3.9 (5) C18—C17—N3—C15 2.8 (4) C6—C1—C8—N1 −2.2 (3) O4—C17—N3—C19 1.7 (5) C2—C1—C8—N1 174.8 (3) C18—C17—N3—C19 −174.9 (3) N1—C9—C10—O3 38 (2) C16—C15—N3—C17 −176.5 (3) N1—C9—C10—O3′ 8 (4) C14—C15—N3—C17 4.2 (4) N1—C9—C10—N2 −150.7 (3) C16—C15—N3—C19 1.1 (4) C16—C11—C12—F1 179.2 (2) C14—C15—N3—C19 −178.2 (2) N2—C11—C12—F1 2.7 (4) C20—C19—N3—C17 −111.2 (3) C16—C11—C12—C13 1.2 (4) C20—C19—N3—C15 71.1 (3) N2—C11—C12—C13 −175.3 (3) C17—C18—O5—C14 24.1 (5) F1—C12—C13—C14 −178.7 (3) C13—C14—O5—C18 166.1 (3) C11—C12—C13—C14 −0.7 (5) C15—C14—O5—C18 −17.0 (5) C12—C13—C14—O5 177.0 (3)
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+1, −z.
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
C21—H21···O2iii 0.93 2.33 3.244 (5) 168
C19—H19B···O4 0.97 2.30 2.735 (4) 106 C13—H13···O1iv 0.93 2.44 3.354 (4) 170
C9—H9A···O3v 0.97 2.48 3.189 (8) 130
C4—H4B···O4vi 0.97 2.54 3.454 (8) 157
N2—H2···O3v 0.85 (1) 2.04 (2) 2.847 (9) 158 (3)
