organic compounds
Acta Crystallographica Section E Data collection
Structure Reports Rigaku R-AXIS RAPID-II 22684 measured reflections
Online diffractometer 5404 independent reflections
Absorption correction: multi-scan 4801 reflections with I > 2(I)
ISSN 1600-5368 (ABSCOR; Higashi, 1995) Rint = 0.026
Tmin = 0.809, Tmax = 0.969
Bis[(3-chlorobenzyl)ammonium] Refinement
2-phenylpropanedioate dihydrate R[F 2 > 2(F 2)] = 0.030 H atoms treated by a mixture of
wR(F 2) = 0.080 independent and constrained
S = 1.03 refinement
Jerry Joe Ebow Kingsley Harrison,a Robert Kingsford- 5404 reflections max = 0.35 e Å3
Adaboh,a* Kazuma Gotohb and Hiroyuki Ishidab 312 parameters min = 0.28 e Å
3
aDepartment of Chemistry, Faculty of Science, University of Ghana, Box LG56
Legon, Accra, Ghana, and bDepartment of Chemistry, Faculty of Science, Okayama Table 1

University, Okayama 700-8530, Japan Hydrogen-bond geometry (Å, ).
Correspondence e-mail: kadabohs@ug.edu.gh
D—H  A D—H H  A D  A D—H  A
Received 15 July 2010; accepted 26 July 2010 N1—H1A  O2 0.91 1.89 2.7789 (13) 165
N1—H1B  O1i 0.91 1.91 2.7891 (14) 163
Key indicators: single-crystal X-ray study; T = 93 K; mean (C–C) = 0.002 Å; R factor = N1—H1C  O4ii 0.91 1.82 2.7286 (13) 175
0.030; wR factor = 0.080; data-to-parameter ratio = 17.3. N2—H2A  O2 0.91 2.12 2.9783 (13) 157
N2—H2A  O4 0.91 2.40 2.9220 (13) 117
N2—H2B  O5iii 0.91 1.98 2.8530 (14) 159
N2—H2C  O5i 0.91 2.01 2.8863 (13) 162
In the asymmetric unit of the title compound, 2C7H9ClN
+- O5—H5A  O1 0.795 (18) 1.931 (18) 2.7158 (12) 169.2 (16)
C H O 2 i2H O, there are two crystallographically indepen- O5—H5B  O3 0.841 (17) 1.868 (17) 2.6818 (12) 162.6 (15)9 6 4 2 O6—H6A  O1 0.828 (17) 2.060 (17) 2.8559 (13) 161.0 (16)
dent cations, one dianion and two water molecules. The O6—H6B  O3iv 0.856 (17) 1.945 (17) 2.7948 (13) 172.3 (16)
dihedral angle between the two carboxylate groups of the C9—H9  O4 0.95 2.58 3.2035 (15) 123
 C15—H15  O2 0.95 2.39 3.2341 (15) 148dianion is 78.1 (2) . In the crystal, the components are held C22—H22  O3v 0.95 2.58 3.4936 (15) 160
together by N—H  O, O—H  O and C—H  O hydrogen C23—H23A  O6vi 0.99 2.49 3.3424 (15) 144
bonds, forming a layer parallel to the bc plane, with the Symmetry codes: (i) x; y  12;z þ 12; (ii) x;y þ 3; z  12 2; (iii) x;y þ 32; z þ 12; (iv)
hydrophilic and hydrophobic groups located in the inner and x;y þ 2;z þ 1; (v) x; y  1; z; (vi) x;y þ 1;z þ 1.
outer regions of the layers, respectively.
Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell
refinement: PROCESS-AUTO; data reduction: CrystalStructure
Related literature (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92
(Altomare et al., 1994); program(s) used to refine structure:
For related structures, see: Ueda et al. (2005); Gotoh & Ishida
SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3
(2009).
(Farrugia, 1997); software used to prepare material for publication:
CrystalStructure (Rigaku/MSC, 2004).
This work was partly supported by a Grant-in-Aid for
Scientific Research (C) (No. 22550013) from the Japan Society
for the Promotion of Science.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: ZL2291).
Experimental References
Crystal data Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C.,
 Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.2C H ClN+7 9 C9H6O 24 2H2O V = 2371.07 (17) Å3 Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Mr = 499.39 Z = 4 Gotoh, K. & Ishida, H. (2009). Acta Cryst. C65, o534–o538.
Monoclinic, P21=c Mo K radiation
 Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.a = 17.3487 (7) Å  = 0.32 mm 1 Rigaku/MSC (2004). PROCESS-AUTO and CrystalStructure. Rigaku/MSC
b = 9.7903 (5) Å T = 93 K Inc., The Woodlands, Texas, USA.
c = 14.3496 (6) Å 0.36  0.25  0.10 mm Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
 = 103.3832 (12) Ueda, S., Fukunaga, T. & Ishida, H. (2005). Acta Cryst. E61, o1845–o1847.
o2168 Harrison et al. doi:10.1107/S1600536810029764 Acta Cryst. (2010). E66, o2168
supporting information
supporting information
Acta Cryst. (2010). E66, o2168    [https://doi.org/10.1107/S1600536810029764]
Bis[(3-chlorobenzyl)ammonium] 2-phenylpropanedioate dihydrate
Jerry Joe Ebow Kingsley Harrison, Robert Kingsford-Adaboh, Kazuma Gotoh and Hiroyuki 
Ishida
S1. Comment 
The title compound was investigated as part of a structural study on D—H···A hydrogen bonding (D = N, O or C; A = N 
or O) in carboxylic acid and pyridine systems (Ueda et al., 2005; Gotoh & Ishida, 2009).
The molecular structure of the compound and the crystal packing of the molecules viewed along the crystallographic b 
axis are shown in Figures 1 and 2, respectively. In its asymmetric unit the title compound has two crystallographically 
independent cations, one dianion and two water molecules. The two 3-chlorobenzylammonium cations have inverted but 
otherwise virtually indentical conformations as shown by the rotational angle of the ammonium group against the 
remainder of the molecule, N1-C16-C10-C11 = -119.04 (12)° and N2-C23-C17-C18 = 113.49 (12)° for the two groups 
(the two crystallographically independent ions are opposite enantiomers, but as as the structure is centrosymmetric both 
ions are present as racemic pairs throughout the structure).
The C—O bond length in one of the carboxylates is slightly longer than in the other with the respective values of O1—
C1 and O2—C1 being 1.2714 (14) and 1.2501 (14) Å. The O3—C3 and O4—C3 bond lengths in the other carboxylates 
are 1.2559 (14) and 1.2538 (14) Å, respectively, making the carbonyl distance in the latter indistinguishable from the 
single bond due to resonance. The slight difference in the two sets of carbonyl distances may be attributed to the number 
of H bonds their respective O atoms are involved in, as H bonds tend to stabilize negative charge at the O atoms. The 
three O atoms with only two strong H bonds have C-O distances below 1.6 Å, the one with three strong H bonds has a C-
O distance larger than 1.7 Å.
The molecules associate by placement of all the phenyl rings in one direction, while the hydrophilic ammonium and the 
carboxylate ends are oriented towards the other end and are hydrogen bonded to water molecules, resulting in alternating 
hydrophobic and hydrophylic regions respectively in the crystal packing. In the hydrophilic regions the water molecules 
act as donors and acceptors in an extended hydrogen bonding network. Each water molecule serves as a bridge that links 
a 3-chlorobenzylammonium moiety and a phenylmalonate group. This arrangement affords an interconnectivity of water 
and donor protons such that two of the ammonium H atoms are donated to the water O atoms in a short N—H···O contact 
of comparable length [N2—H2B···O5iii = 1.98Å and N2—H2C···O5i = 2.01Å; Table 1], while the water H atoms are 
donated to the carboxylate O atoms [O5—H5A···O1 = 1.931 (18), O5—H5B···O3i = 1.868 (17), O6—H6A···O1 = 
2.060 (17) and O6—H6B···O3iv = 1.945 (17) Å; Table 1].
In the hydrophobic regions the chloro-substituted aromatic rings show some stacking of parallel-shifted aromatic rings 
with each other, but the shortest centroid to centroid distance is larger than 4.3 Å and the interplanar separation is with 
greater than 3.6 Å also rather long for an attractive π-π stacking interaction. In the absence of any other directional 
interactions in the hydrophobic section of the structure it thus can be assumed that the crystal packing in these layers is 
likely to be dominated by shape recognition via dispersion forces.
Acta Cryst. (2010). E66, o2168    sup-1
supporting information
S2. Experimental 
Single crystals of the title compound were grown by slow evaporation of a water-ethanol solution (1:1 v/v; 20 ml) of 3-
chlorobenzylamine (0.71 g, 5.0 mmol) and phenylmalonic acid (0.45 g, 0.25 mmol) at room temperature.
S3. Refinement 
All H atoms were found in a difference Fourier map. Positional parameters of the water H atoms were refined, with 
Uiso(H) = 1.2Ueq(O). The NH +3  groups were refined as rigid groups (N—H = 0.91 Å), with Uiso(H) = 1.5Ueq(N), allowing 
for rotation around the C—N bonds. Other C-bound H atoms were refined as riding, with C—H = 0.95–1.00 Å, and with 
Uiso(H) = 1.2Ueq(C).
Figure 1
ORTEP-3 (Farrugia, 1997) diagram of 3-chlorobenzylammonium phenylmalonate dihydrate, showing the atom-
numbering scheme. Displacement ellipsoids for non-hydrogen atoms are plotted at 50% probability and hydrogen atoms 
are shown as small spheres of arbitrary radii. 
Acta Cryst. (2010). E66, o2168    sup-2
supporting information
Figure 2
A part of the crystal packing of the crystal structure of 3-chlorobenzylammonium phenylmalonate dihydrate, viewed 
down the b axis showing a network of hydrogen bonds. Hydrogen bonds are shown by broken lines. Colour codes for 
residues: RED & BLACK = 3-chlorobenzylammonium; GREEN = phenylmalonate; BLUE & YELLOW = water 
molecules. 
Bis[(3-chlorobenzyl)ammonium] 2-phenylpropanedioate dihydrate 
Crystal data 
2C H + 2−7 9ClN ·C9H6O4 ·2H2O F(000) = 1048.00
Mr = 499.39 Dx = 1.399 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc Cell parameters from 19587 reflections
a = 17.3487 (7) Å θ = 3.2–27.5°
b = 9.7903 (5) Å µ = 0.32 mm−1
c = 14.3496 (6) Å T = 93 K
β = 103.3832 (12)° Block, colorless
V = 2371.07 (17) Å3 0.36 × 0.25 × 0.10 mm
Z = 4
Data collection 
Rigaku R-AXIS RAPID-II 5404 independent reflections
diffractometer 4801 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1 Rint = 0.026
ω scans θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan h = −22→22
(ABSCOR; Higashi, 1995) k = −12→12
Tmin = 0.809, Tmax = 0.969 l = −17→18
22684 measured reflections
Acta Cryst. (2010). E66, o2168    sup-3
supporting information
Refinement 
Refinement on F2 H atoms treated by a mixture of independent 
Least-squares matrix: full and constrained refinement
R[F2 > 2σ(F2)] = 0.030 w = 1/[σ2(F 2o ) + (0.045P)2 + 0.8144P] 
wR(F2) = 0.080 where P = (F 2 + 2F 2o c )/3
S = 1.03 (Δ/σ)max = 0.001
5404 reflections Δρmax = 0.35 e Å−3
312 parameters Δρmin = −0.28 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
Cl1 0.439729 (18) 0.35812 (3) 0.16174 (2) 0.02351 (8)
Cl2 0.456436 (18) 0.67256 (3) 0.58413 (2) 0.02689 (9)
O1 0.01868 (5) 0.88588 (8) 0.27920 (6) 0.01579 (17)
O2 0.12915 (5) 0.76812 (8) 0.33753 (6) 0.01682 (17)
O3 0.10538 (5) 1.13611 (8) 0.50629 (6) 0.01916 (18)
O4 0.11331 (5) 0.90909 (8) 0.52121 (6) 0.01844 (18)
O5 −0.03654 (5) 0.85786 (9) 0.08701 (6) 0.01747 (17)
H5A −0.0194 (10) 0.8553 (16) 0.1434 (13) 0.021*
H5B −0.0583 (9) 0.7825 (18) 0.0693 (11) 0.021*
O6 −0.06079 (6) 0.68283 (9) 0.36504 (7) 0.02034 (18)
H6A −0.0353 (10) 0.7262 (17) 0.3327 (12) 0.024*
H6B −0.0720 (9) 0.7440 (17) 0.4024 (12) 0.024*
N1 0.10896 (6) 0.55243 (10) 0.20825 (7) 0.01391 (19)
H1A 0.1134 0.6328 0.2409 0.021*
H1B 0.0613 0.5135 0.2079 0.021*
H1C 0.1126 0.5684 0.1469 0.021*
N2 0.09606 (6) 0.61282 (10) 0.50244 (7) 0.0162 (2)
H2A 0.1111 0.6780 0.4650 0.024*
H2B 0.0510 0.6400 0.5193 0.024*
H2C 0.0869 0.5329 0.4693 0.024*
C1 0.09030 (7) 0.87682 (11) 0.32604 (7) 0.0126 (2)
C2 0.12851 (6) 1.00848 (11) 0.37329 (8) 0.0127 (2)
H2 0.1016 1.0877 0.3352 0.015*
C3 0.11362 (6) 1.01818 (11) 0.47553 (8) 0.0136 (2)
C4 0.21663 (7) 1.01807 (11) 0.37713 (8) 0.0138 (2)
C5 0.24195 (7) 1.08640 (12) 0.30411 (8) 0.0173 (2)
H5 0.2040 1.1274 0.2534 0.021*
Acta Cryst. (2010). E66, o2168    sup-4
supporting information
C6 0.32227 (8) 1.09505 (13) 0.30482 (10) 0.0225 (3)
H6 0.3387 1.1402 0.2541 0.027*
C7 0.37820 (7) 1.03784 (13) 0.37942 (10) 0.0238 (3)
H7 0.4330 1.0452 0.3806 0.029*
C8 0.35360 (7) 0.96960 (13) 0.45254 (9) 0.0227 (3)
H8 0.3918 0.9301 0.5037 0.027*
C9 0.27344 (7) 0.95889 (12) 0.45108 (9) 0.0188 (2)
H9 0.2572 0.9109 0.5008 0.023*
C10 0.25586 (7) 0.50774 (12) 0.25364 (8) 0.0152 (2)
C11 0.30228 (7) 0.42829 (12) 0.20729 (8) 0.0170 (2)
H11 0.2804 0.3502 0.1715 0.020*
C12 0.38073 (7) 0.46418 (12) 0.21377 (8) 0.0171 (2)
C13 0.41351 (7) 0.58019 (12) 0.26201 (9) 0.0195 (2)
H13 0.4672 0.6038 0.2655 0.023*
C14 0.36614 (7) 0.66165 (13) 0.30541 (9) 0.0215 (3)
H14 0.3874 0.7430 0.3374 0.026*
C15 0.28821 (7) 0.62547 (12) 0.30251 (9) 0.0188 (2)
H15 0.2569 0.6808 0.3338 0.023*
C16 0.17387 (7) 0.45831 (12) 0.25573 (9) 0.0175 (2)
H16A 0.1651 0.3681 0.2238 0.021*
H16B 0.1710 0.4456 0.3233 0.021*
C17 0.23541 (7) 0.54046 (12) 0.56655 (8) 0.0163 (2)
C18 0.30291 (7) 0.62186 (12) 0.58334 (8) 0.0175 (2)
H18 0.3022 0.7109 0.6094 0.021*
C19 0.37141 (7) 0.57119 (13) 0.56150 (9) 0.0197 (2)
C20 0.37432 (8) 0.44271 (13) 0.52259 (9) 0.0227 (3)
H20 0.4216 0.4105 0.5074 0.027*
C21 0.30677 (8) 0.36155 (13) 0.50613 (9) 0.0227 (3)
H21 0.3077 0.2730 0.4794 0.027*
C22 0.23794 (7) 0.40932 (12) 0.52858 (9) 0.0191 (2)
H22 0.1923 0.3527 0.5181 0.023*
C23 0.16042 (7) 0.59252 (12) 0.59052 (8) 0.0176 (2)
H23A 0.1425 0.5264 0.6332 0.021*
H23B 0.1715 0.6803 0.6253 0.021*
Atomic displacement parameters (Å2) 
U11 U22 U33 U12 U13 U23
Cl1 0.01977 (15) 0.02374 (15) 0.02822 (16) 0.00445 (11) 0.00803 (12) −0.00380 (12)
Cl2 0.01780 (15) 0.02676 (17) 0.03560 (18) −0.00173 (11) 0.00518 (13) 0.00059 (13)
O1 0.0139 (4) 0.0185 (4) 0.0145 (4) 0.0003 (3) 0.0021 (3) −0.0018 (3)
O2 0.0175 (4) 0.0127 (4) 0.0199 (4) 0.0010 (3) 0.0035 (3) −0.0034 (3)
O3 0.0283 (5) 0.0130 (4) 0.0172 (4) 0.0028 (3) 0.0073 (4) −0.0026 (3)
O4 0.0290 (5) 0.0124 (4) 0.0146 (4) −0.0008 (3) 0.0065 (3) 0.0003 (3)
O5 0.0221 (4) 0.0164 (4) 0.0127 (4) −0.0040 (3) 0.0017 (3) −0.0005 (3)
O6 0.0251 (5) 0.0176 (4) 0.0199 (4) −0.0012 (3) 0.0084 (4) −0.0022 (3)
N1 0.0148 (4) 0.0134 (4) 0.0135 (4) −0.0012 (4) 0.0031 (4) −0.0012 (3)
N2 0.0158 (5) 0.0133 (5) 0.0197 (5) 0.0012 (4) 0.0043 (4) 0.0015 (4)
Acta Cryst. (2010). E66, o2168    sup-5
supporting information
C1 0.0146 (5) 0.0151 (5) 0.0088 (5) −0.0007 (4) 0.0044 (4) −0.0011 (4)
C2 0.0157 (5) 0.0101 (5) 0.0119 (5) 0.0011 (4) 0.0027 (4) 0.0003 (4)
C3 0.0136 (5) 0.0139 (5) 0.0129 (5) −0.0004 (4) 0.0020 (4) −0.0017 (4)
C4 0.0162 (5) 0.0100 (5) 0.0149 (5) −0.0005 (4) 0.0028 (4) −0.0031 (4)
C5 0.0200 (6) 0.0140 (5) 0.0180 (5) −0.0005 (4) 0.0045 (5) −0.0008 (4)
C6 0.0238 (6) 0.0185 (6) 0.0286 (6) −0.0024 (5) 0.0127 (5) −0.0013 (5)
C7 0.0167 (6) 0.0196 (6) 0.0356 (7) −0.0015 (5) 0.0074 (5) −0.0074 (5)
C8 0.0193 (6) 0.0204 (6) 0.0252 (6) 0.0036 (5) −0.0016 (5) −0.0021 (5)
C9 0.0204 (6) 0.0176 (6) 0.0174 (5) 0.0006 (4) 0.0022 (5) 0.0005 (4)
C10 0.0147 (5) 0.0146 (5) 0.0153 (5) 0.0004 (4) 0.0012 (4) 0.0030 (4)
C11 0.0182 (5) 0.0143 (5) 0.0177 (5) −0.0007 (4) 0.0022 (5) −0.0003 (4)
C12 0.0172 (5) 0.0162 (5) 0.0177 (5) 0.0036 (4) 0.0038 (4) 0.0015 (4)
C13 0.0140 (5) 0.0191 (6) 0.0247 (6) −0.0015 (4) 0.0028 (5) 0.0010 (5)
C14 0.0200 (6) 0.0166 (6) 0.0265 (6) −0.0024 (4) 0.0027 (5) −0.0042 (5)
C15 0.0179 (6) 0.0178 (6) 0.0208 (6) 0.0010 (4) 0.0046 (5) −0.0022 (4)
C16 0.0159 (5) 0.0152 (5) 0.0210 (6) −0.0002 (4) 0.0036 (5) 0.0039 (4)
C17 0.0181 (5) 0.0166 (5) 0.0134 (5) 0.0041 (4) 0.0023 (4) 0.0027 (4)
C18 0.0197 (6) 0.0154 (5) 0.0168 (5) 0.0024 (4) 0.0028 (5) 0.0009 (4)
C19 0.0174 (5) 0.0212 (6) 0.0192 (6) 0.0007 (5) 0.0014 (5) 0.0040 (5)
C20 0.0201 (6) 0.0243 (6) 0.0237 (6) 0.0072 (5) 0.0053 (5) 0.0009 (5)
C21 0.0262 (6) 0.0172 (6) 0.0231 (6) 0.0052 (5) 0.0025 (5) −0.0024 (5)
C22 0.0194 (6) 0.0165 (5) 0.0196 (6) 0.0007 (4) 0.0007 (5) 0.0003 (4)
C23 0.0182 (5) 0.0175 (5) 0.0165 (5) 0.0018 (4) 0.0031 (5) −0.0006 (4)
Geometric parameters (Å, º) 
Cl1—C12 1.7427 (12) C8—C9 1.3899 (17)
Cl2—C19 1.7448 (13) C8—H8 0.9500
O1—C1 1.2714 (14) C9—H9 0.9500
O2—C1 1.2501 (14) C10—C11 1.3941 (16)
O3—C3 1.2559 (14) C10—C15 1.3975 (16)
O4—C3 1.2538 (14) C10—C16 1.5095 (16)
O5—H5A 0.795 (18) C11—C12 1.3878 (16)
O5—H5B 0.840 (18) C11—H11 0.9500
O6—H6A 0.828 (18) C12—C13 1.3822 (17)
O6—H6B 0.855 (17) C13—C14 1.3914 (18)
N1—C16 1.4921 (14) C13—H13 0.9500
N1—H1A 0.9100 C14—C15 1.3888 (17)
N1—H1B 0.9100 C14—H14 0.9500
N1—H1C 0.9100 C15—H15 0.9500
N2—C23 1.4935 (15) C16—H16A 0.9900
N2—H2A 0.9100 C16—H16B 0.9900
N2—H2B 0.9100 C17—C18 1.3906 (17)
N2—H2C 0.9100 C17—C22 1.3994 (16)
C1—C2 1.5338 (15) C17—C23 1.5092 (16)
C2—C4 1.5199 (15) C18—C19 1.3889 (17)
C2—C3 1.5503 (15) C18—H18 0.9500
C2—H2 1.0000 C19—C20 1.3818 (18)
Acta Cryst. (2010). E66, o2168    sup-6
supporting information
C4—C9 1.3960 (16) C20—C21 1.3901 (19)
C4—C5 1.3969 (16) C20—H20 0.9500
C5—C6 1.3937 (17) C21—C22 1.3880 (18)
C5—H5 0.9500 C21—H21 0.9500
C6—C7 1.3858 (19) C22—H22 0.9500
C6—H6 0.9500 C23—H23A 0.9900
C7—C8 1.3916 (19) C23—H23B 0.9900
C7—H7 0.9500
H5A—O5—H5B 108.4 (15) C15—C10—C16 121.68 (11)
H6A—O6—H6B 102.7 (15) C12—C11—C10 119.51 (11)
C16—N1—H1A 109.5 C12—C11—H11 120.2
C16—N1—H1B 109.5 C10—C11—H11 120.2
H1A—N1—H1B 109.5 C13—C12—C11 121.67 (11)
C16—N1—H1C 109.5 C13—C12—Cl1 119.33 (9)
H1A—N1—H1C 109.5 C11—C12—Cl1 118.99 (9)
H1B—N1—H1C 109.5 C12—C13—C14 118.56 (11)
C23—N2—H2A 109.5 C12—C13—H13 120.7
C23—N2—H2B 109.5 C14—C13—H13 120.7
H2A—N2—H2B 109.5 C15—C14—C13 120.81 (11)
C23—N2—H2C 109.5 C15—C14—H14 119.6
H2A—N2—H2C 109.5 C13—C14—H14 119.6
H2B—N2—H2C 109.5 C14—C15—C10 120.02 (11)
O2—C1—O1 124.07 (10) C14—C15—H15 120.0
O2—C1—C2 119.50 (10) C10—C15—H15 120.0
O1—C1—C2 116.40 (9) N1—C16—C10 114.08 (9)
C4—C2—C1 113.34 (9) N1—C16—H16A 108.7
C4—C2—C3 110.39 (9) C10—C16—H16A 108.7
C1—C2—C3 108.67 (9) N1—C16—H16B 108.7
C4—C2—H2 108.1 C10—C16—H16B 108.7
C1—C2—H2 108.1 H16A—C16—H16B 107.6
C3—C2—H2 108.1 C18—C17—C22 119.48 (11)
O4—C3—O3 125.78 (10) C18—C17—C23 120.18 (11)
O4—C3—C2 117.67 (9) C22—C17—C23 120.33 (11)
O3—C3—C2 116.51 (10) C19—C18—C17 119.10 (11)
C9—C4—C5 118.66 (11) C19—C18—H18 120.4
C9—C4—C2 121.95 (10) C17—C18—H18 120.4
C5—C4—C2 119.39 (10) C20—C19—C18 121.97 (12)
C6—C5—C4 120.74 (11) C20—C19—Cl2 118.99 (10)
C6—C5—H5 119.6 C18—C19—Cl2 119.04 (10)
C4—C5—H5 119.6 C19—C20—C21 118.74 (11)
C7—C6—C5 120.08 (12) C19—C20—H20 120.6
C7—C6—H6 120.0 C21—C20—H20 120.6
C5—C6—H6 120.0 C22—C21—C20 120.31 (12)
C6—C7—C8 119.63 (12) C22—C21—H21 119.8
C6—C7—H7 120.2 C20—C21—H21 119.8
C8—C7—H7 120.2 C21—C22—C17 120.38 (11)
C9—C8—C7 120.34 (12) C21—C22—H22 119.8
Acta Cryst. (2010). E66, o2168    sup-7
supporting information
C9—C8—H8 119.8 C17—C22—H22 119.8
C7—C8—H8 119.8 N2—C23—C17 111.54 (9)
C8—C9—C4 120.53 (11) N2—C23—H23A 109.3
C8—C9—H9 119.7 C17—C23—H23A 109.3
C4—C9—H9 119.7 N2—C23—H23B 109.3
C11—C10—C15 119.37 (11) C17—C23—H23B 109.3
C11—C10—C16 118.79 (10) H23A—C23—H23B 108.0
O2—C1—C2—C4 35.03 (14) C10—C11—C12—C13 −2.61 (18)
O1—C1—C2—C4 −147.07 (10) C10—C11—C12—Cl1 176.06 (9)
O2—C1—C2—C3 −88.10 (12) C11—C12—C13—C14 0.44 (18)
O1—C1—C2—C3 89.81 (11) Cl1—C12—C13—C14 −178.22 (10)
C4—C2—C3—O4 −89.86 (12) C12—C13—C14—C15 1.64 (19)
C1—C2—C3—O4 35.02 (13) C13—C14—C15—C10 −1.55 (19)
C4—C2—C3—O3 87.97 (12) C11—C10—C15—C14 −0.64 (18)
C1—C2—C3—O3 −147.15 (10) C16—C10—C15—C14 174.74 (11)
C1—C2—C4—C9 −85.18 (13) C11—C10—C16—N1 −119.05 (12)
C3—C2—C4—C9 36.99 (14) C15—C10—C16—N1 65.55 (14)
C1—C2—C4—C5 93.96 (12) C22—C17—C18—C19 0.32 (17)
C3—C2—C4—C5 −143.87 (10) C23—C17—C18—C19 179.41 (10)
C9—C4—C5—C6 0.20 (17) C17—C18—C19—C20 0.70 (18)
C2—C4—C5—C6 −178.97 (10) C17—C18—C19—Cl2 −179.13 (9)
C4—C5—C6—C7 −1.26 (18) C18—C19—C20—C21 −0.84 (19)
C5—C6—C7—C8 1.21 (19) Cl2—C19—C20—C21 178.99 (10)
C6—C7—C8—C9 −0.12 (19) C19—C20—C21—C22 −0.04 (19)
C7—C8—C9—C4 −0.95 (18) C20—C21—C22—C17 1.05 (19)
C5—C4—C9—C8 0.90 (17) C18—C17—C22—C21 −1.18 (18)
C2—C4—C9—C8 −179.95 (11) C23—C17—C22—C21 179.73 (11)
C15—C10—C11—C12 2.67 (17) C18—C17—C23—N2 113.48 (12)
C16—C10—C11—C12 −172.85 (10) C22—C17—C23—N2 −67.43 (14)
Hydrogen-bond geometry (Å, º) 
D—H···A D—H H···A D···A D—H···A
N1—H1A···O2 0.91 1.89 2.7789 (13) 165
N1—H1B···O1i 0.91 1.91 2.7891 (14) 163
N1—H1C···O4ii 0.91 1.82 2.7286 (13) 175
N2—H2A···O2 0.91 2.12 2.9783 (13) 157
N2—H2A···O4 0.91 2.40 2.9220 (13) 117
N2—H2B···O5iii 0.91 1.98 2.8530 (14) 159
N2—H2C···O5i 0.91 2.01 2.8863 (13) 162
O5—H5A···O1 0.795 (18) 1.931 (18) 2.7158 (12) 169.2 (16)
O5—H5B···O3i 0.841 (17) 1.868 (17) 2.6818 (12) 162.6 (15)
O6—H6A···O1 0.828 (17) 2.060 (17) 2.8559 (13) 161.0 (16)
O6—H6B···O3iv 0.856 (17) 1.945 (17) 2.7948 (13) 172.3 (16)
C9—H9···O4 0.95 2.58 3.2035 (15) 123
C15—H15···O2 0.95 2.39 3.2341 (15) 148
Acta Cryst. (2010). E66, o2168    sup-8
supporting information
C22—H22···O3v 0.95 2.58 3.4936 (15) 160
C23—H23A···O6vi 0.99 2.49 3.3424 (15) 144
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, −y+3/2, z−1/2; (iii) x, −y+3/2, z+1/2; (iv) −x, −y+2, −z+1; (v) x, y−1, z; (vi) −x, −y+1, −z+1.
Acta Cryst. (2010). E66, o2168    sup-9