Hydro­gen bonding and C—H...O interactions in 3-(3-amino­phthal­imido)phthalic acid dihydrate

The title compound, C₁₆H₁₀N₂O₆·2H₂O, crystallized in the centrosymmetric triclinic space group P with one organic mol­ecule and two water mol­ecules as the asymmetric unit. Eight intermolecular hydrogen bonds have donor...acceptor distances in the range 2.602 (2)–3.289 (2) Å, with angles in the range 137 (2)–177 (2)°. These generate a three-dimensional hydrogen-bond network. There is a single intramolecular hydrogen bond. There are six significant intermolecular C—H...O interactions with H...O distances in the range 2.39–2.74 Å, and C—H...O angles in the range 131–157°.

S1. Comment

This report is one of a series on hydrogen bonding and C—H···O interactions in carboxylic acids. A definitive synthesis, isolation and characterization of 3-aminophthalic acid by Bogert & Jouard (1909) demonstrated that pure 3-aminophthalic acid is colorless, not yellow as then commonly thought, and that in aqueous solution, even at room temperature, it reacts readily to form a yellow-orange product. They characterized this product, (I), only by its melting point and by its nitrogen content, which they reported as 9.2% [for (I), the theoretical nitrogen content is 7.7%, or, if anhydrous, 8.6%]. Compound (I) was later fully characterized in the work of Fuortes & Gaetani (1962). In the present study, (I) crystallized in the centrosymmetric triclinic space group P1 with one organic molecule and two water molecules as the asymmetric unit. The refined asymmetric unit and the labeling scheme are given in Fig. 1. One intramolecular and eight intermolecular hydrogen bonds and six leading intermolecular C—H···O interactions (Taylor & Kennard, 1982; Steiner & Desiraju, 1998) are present in this structure. The geometric parameters of these are given in Table 2. It may be noted that the hydrogen bonds involving the amino N atoms, H1N1 and H2N1, are the weakest of those tabulated, but they are the sole intermolecular hydrogen bonds involving these H atoms; moreover, these interactions, together with the intramolecular bond involving H1N1, undoubtedly play a significant role in determining the observed orientation of the amino group. Each acid molecule is linked directly to 3 neighboring acid molecules and to 5 neighboring water molecules by these hydrogen bonds as shown for a central molecule in the stereodiagram, Fig. 2. The results of basic first- and second-level graph-set analysis (Bernstein et al., 1995) involving the intermolecular hydrogen bonds, labeled a-h for this purpose in the order of their appearance in Table 2, are given in Table 3. As expected with two water molecules in the asymmetric unit in general positions, finite graphs are very prominent (26 of the 36 entries). The four chains propagate variously along [100], [010] (2) and [011] and suffice to generate a three-dimensional network of interactions. O4 is the only O atom not involved as an acceptor of a (conventional) hydrogen bond (Table 2). Thus, it is not unexpected to find it involved in two significant C—H···O interactions (Table 2). Fig. 1 makes apparent a third-level (adf) ring, R₃³(11).

The five-membered ring is in an envelope conformation: the maximum deviation of any of the four `body' atoms, N2, C1, C2 and C7, from the best-fit plane describing them is 0.000 (2) Å, while the `flap' atom, C8, is 0.043 (2) Å from that plane.

Selected bond distances and angles of (I) are given in Table 1. A l l distances and angles fall within normal limits. For structural comparisons with (I), N-(o-nitrophenyl)phthalimide (Voliotis et al., 1984) and N-(o-tolyl)phthalimide (Bocelli & Cantoni, 1989), each with one phenyl substituent ortho to C9, appear well suited. Taking into account that (I) is characterized at 150 K rather than at room temperature, the agreement of the geometries of the five- membered rings in these three compounds is quite satisfactory. Also, for example, the N2—C9 distance (present nomenclature) is 1.441 (2) Å in (I), 1.425 (3) and 1.452 (9) Å in the nitrophenyl and tolyl phthalimides, respectively. The dihedral angles between the phthalimide core plane and the phenyl-ring plane are quite different, however, being 83.5 (1), 54.0 (2) and 70.7 (2)°, respectively. In (I), the closest intermolecular approaches, excluding pairs of atoms involved in hydrogen-bonded groups or in the tabulated C—H···O interactions, are between O2 and O2^iv (iv = 1 − x, 2 − y, 1 − z) and fall short of the corresponding Bondi (1964) van der Waals radius sum by 0.03 Å.

S2. Experimental

Technical grade 3-aminophthalic acid was obtained from Aldrich Chemical Company as a yellow powder. This was dissolved in water at room temperature, and the solution was filtered. Evaporation of this solution produced suitable crystals of the title substance (see Comment).

S3. Refinement

Fourier difference methods were used to locate initial H-atom positions, and these H atoms were refined. Refined C—H distances ranged from 0.92 (2) to 1.00 (1) Å, with mean value 0.96 (3) Å; their U_iso values ranged from 0.4 to 1.4 × the U_eq values of the attached C atoms. These H atoms were then made canonical, with C—H = 0.98 Å and U_iso = 1.2 × U_eq of the attached C atom.

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1995); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN and PLATON (Spek, 1990).

Figures

	Fig. 1. Displacement ellipsoids at the 50% probability level. Intermolecular hydrogen bonds within the asymmetric unit are depicted by dashed lines, the intramolecular bond by a dotted line.
	Fig. 2. Stereoview of the packing, viewed down the c axis toward the origin.

(I)

Crystal data

C16H10N2O6·2H2O	Z = 2
Mr = 362.30	F(000) = 376
Triclinic, P1	Dx = 1.519 Mg m^−3
a = 7.5608 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0632 (2) Å	Cell parameters from 20808 reflections
c = 12.7245 (3) Å	θ = 1.7–27.5°
α = 69.481 (1)°	µ = 0.12 mm^−1
β = 82.764 (1)°	T = 150 K
γ = 76.229 (2)°	Uncut plate, yellow-orange (golden)
V = 792.29 (3) Å^3	0.31 × 0.23 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	2917 reflections with I > 2σI
Radiation source: X-ray tube	Rint = 0.037
Graphite monochromator	θmax = 27.5°
ω scans with κ offsets	h = −9→9
20808 measured reflections	k = −11→11
3628 independent reflections	l = −16→16

Refinement

Refinement on F^2	267 parameters
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.049	Weighting scheme based on measured s.u.'s w = 1/[σ^2cs + (0.037I)^2]
wR(F^2) = 0.125	(Δ/σ)max = 0.0004
S = 1.98	Δρmax = 0.59 e Å^−3
3627 reflections	Δρmin = −0.33 e Å^−3

Special details

Experimental. The Laue group assignment, and the centrosymmetry indicated by the intensity statistics led to assignment of the space group as P-1 (No. 2); since refinement proceeded well, it was adopted. Fourier difference methods were used to locate initial H atom positions, and these H atoms were refined. Refined C—H distances ranged from 0.92 (2) to 1.00 (1) Å, with mean value 0.96 (3) Å; their U_iso values ranged from 0.4 to 1.4 times the U_eq values of the attached C atoms. These H atoms were then made canonical, with C—H = 0.98 Å and U_iso = 1.2 × U_eq of the attached C atom. In the later stages of refinement the extinction coefficient was predicted to be negative, so was not included in the model. One reflection, 2 2 1, was removed early in the refinement since it was grossly deviant. The maximum peak in the final difference map occurs ~1.2 Å from O8, but not in a position to be a potential H atom, the maximum negative peak ~0.8 Å from O6.

Geometry. Table of Least-Squares Planes ——————————

————– Plane number 1 —————

Atoms Defining Plane Distance e.s.d. C1 (1) 0.0067 0.0014 C2 (1) −0.0016 0.0014 C3 (1) −0.0045 0.0015 C4 (1) 0.0066 0.0016 C5 (1) 0.0000 0.0016 C6 (1) −0.0068 0.0015

Mean deviation from plane is 0.0044 angstroms Chi-squared: 75.5

————– Plane number 2 —————

Atoms Defining Plane Distance e.s.d. C1 (1) −0.0055 0.0014 C2 (1) 0.0138 0.0014 C7 (1) −0.0060 0.0014 C8 (1) −0.0186 0.0014 N2 (1) 0.0115 0.0012

Additional Atoms Distance O1 (1) −0.0264 O2 (1) −0.0829

Mean deviation from plane is 0.0111 angstroms Chi-squared: 417.4

Dihedral angles between least-squares planes plane plane angle 2 1 1.13

————– Plane number 3 —————

Atoms Defining Plane Distance e.s.d. O1 (1) −0.0214 0.0012 O2 (1) −0.0292 0.0011 N2 (1) 0.0466 0.0012 C1 (1) −0.0143 0.0014 C2 (1) 0.0201 0.0014 C7 (1) 0.0037 0.0014 C8 (1) 0.0156 0.0014

Mean deviation from plane is 0.0216 angstroms Chi-squared: 3147.4

Dihedral angles between least-squares planes plane plane angle 3 1 2.03 3 2 1.13

————– Plane number 4 —————

Atoms Defining Plane Distance e.s.d. C1 (1) 0.0032 0.0014 C2 (1) 0.0068 0.0014 C3 (1) 0.0088 0.0015 C4 (1) 0.0118 0.0016 C5 (1) −0.0065 0.0016 C6 (1) −0.0179 0.0015 C7 (1) 0.0076 0.0014 C8 (1) −0.0312 0.0014 N2 (1) 0.0118 0.0012

Additional Atoms Distance O1 (1) −0.0003 O2 (1) −0.1082

Mean deviation from plane is 0.0117 angstroms Chi-squared: 867.8

Dihedral angles between least-squares planes plane plane angle 4 1 0.49 4 2 0.64 4 3 1.59

————– Plane number 5 —————

Atoms Defining Plane Distance e.s.d. C9 (1) 0.0092 0.0014 C10 (1) −0.0073 0.0014 C11 (1) −0.0006 0.0014 C12 (1) 0.0075 0.0015 C13 (1) −0.0059 0.0015 C14 (1) −0.0029 0.0015

Mean deviation from plane is 0.0056 angstroms Chi-squared: 111.7

Dihedral angles between least-squares planes plane plane angle 5 1 96.02 5 2 97.15 5 3 97.76 5 4 96.51

————– Plane number 6 —————

Atoms Defining Plane Distance e.s.d. C15 (1) 0.0000 O3 (1) 0.0000 O4 (1) 0.0000

Mean deviation from plane is 0.0000 angstroms Chi-squared: 0.0

Dihedral angles between least-squares planes plane plane angle 6 1 130.49 6 2 130.49 6 3 131.38 6 4 130.53 6 5 88.90

————– Plane number 7 —————

Atoms Defining Plane Distance e.s.d. O5 (1) 0.0000 O6 (1) 0.0000 C16 (1) 0.0000

Mean deviation from plane is 0.0000 angstroms Chi-squared: 0.0

Dihedral angles between least-squares planes plane plane angle 7 1 87.02 7 2 85.89 7 3 85.15 7 4 86.53 7 5 171.44 7 6 95.21

The C1—C6 ring is closely planar, the maximum deviation of any of its atoms from the best-fit plane describing them being 0.007 (2) Å. The dihedral angle between this plane and the amino-group plane is 18 (1) °. The dihedral angle between these two planes is 0.4 (1) °. The phthalimide core, atoms C1—C8 and N2, is described by a best-fit plane from which their maximum deviation is 0.032 (2) Å. The C9—C14 phenyl ring is also closely planar, the maximum deviation of any of its atoms from the best-fit plane describing them being 0.009 (2) Å. The dihedral angle between this latter plane and the phthalimide core plane is 83.5 (1) °, between it and the plane of carboxyl group C15—O3—O4 is 88.9 (2) °, and between it and the plane of carboxyl group C16—O5—O6 is 8.6 (2) °. These features can be seen in the packing diagram, Fig. 2.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.7732 (2)	0.6492 (1)	0.21581 (9)	0.0317 (3)
O2	0.4237 (1)	0.9118 (1)	0.44394 (9)	0.0300 (3)
O3	0.8102 (2)	1.0879 (1)	0.3024 (1)	0.0353 (3)
O4	0.9659 (2)	0.9447 (1)	0.1958 (1)	0.0355 (3)
O5	0.6786 (2)	1.4220 (1)	−0.07808 (9)	0.0319 (3)
O6	0.8605 (2)	1.3033 (1)	0.0654 (1)	0.0431 (4)
O7	1.0642 (2)	1.4215 (1)	0.1724 (1)	0.0299 (3)
O8	1.1062 (2)	1.1288 (1)	0.3634 (1)	0.0376 (4)
N1	0.5299 (2)	0.6613 (2)	0.6746 (1)	0.0383 (4)
N2	0.5906 (2)	0.8165 (1)	0.3061 (1)	0.0230 (3)
C1	0.7352 (2)	0.5683 (2)	0.4209 (1)	0.0241 (4)
C2	0.6318 (2)	0.6519 (2)	0.4890 (1)	0.0236 (4)
C3	0.6284 (2)	0.5833 (2)	0.6063 (1)	0.0266 (4)
C4	0.7367 (2)	0.4264 (2)	0.6486 (1)	0.0301 (4)
C5	0.8355 (2)	0.3464 (2)	0.5794 (1)	0.0306 (4)
C6	0.8371 (2)	0.4148 (2)	0.4630 (1)	0.0285 (4)
C7	0.7095 (2)	0.6740 (2)	0.3022 (1)	0.0244 (4)
C8	0.5342 (2)	0.8075 (2)	0.4181 (1)	0.0236 (4)
C9	0.5361 (2)	0.9554 (2)	0.2088 (1)	0.0225 (4)
C10	0.6517 (2)	1.0634 (2)	0.1639 (1)	0.0224 (4)
C11	0.6008 (2)	1.1972 (2)	0.0685 (1)	0.0233 (4)
C12	0.4358 (2)	1.2210 (2)	0.0210 (1)	0.0250 (4)
C13	0.3205 (2)	1.1145 (2)	0.0680 (1)	0.0265 (4)
C14	0.3710 (2)	0.9807 (2)	0.1624 (1)	0.0258 (4)
C15	0.8291 (2)	1.0276 (2)	0.2198 (1)	0.0250 (4)
C16	0.7251 (2)	1.3119 (2)	0.0196 (1)	0.0257 (4)
H1N1	0.446 (3)	0.759 (3)	0.642 (2)	0.059 (6)*
H1	0.933 (3)	1.083 (3)	0.330 (2)	0.075 (7)*
H1O7	0.975 (3)	1.488 (3)	0.184 (2)	0.060 (7)*
H1O8	1.227 (4)	1.039 (3)	0.398 (2)	0.096 (9)*
H2N1	0.519 (3)	0.601 (3)	0.753 (2)	0.061 (6)*
H2O7	1.011 (3)	1.387 (2)	0.125 (2)	0.051 (6)*
H2	0.762 (3)	1.478 (2)	−0.102 (2)	0.044 (6)*
H2O8	1.138 (5)	1.224 (4)	0.301 (3)	0.13 (1)*
H4	0.7412	0.3730	0.7301	0.036*
H5	0.9073	0.2375	0.6131	0.037*
H6	0.9070	0.3569	0.4139	0.034*
H12	0.4009	1.3142	−0.0464	0.030*
H13	0.2036	1.1333	0.0349	0.032*
H14	0.2901	0.9046	0.1958	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0330 (6)	0.0313 (6)	0.0264 (6)	−0.0006 (5)	−0.0007 (5)	−0.0087 (5)
O2	0.0287 (6)	0.0289 (6)	0.0310 (6)	−0.0010 (5)	−0.0028 (5)	−0.0109 (5)
O3	0.0279 (7)	0.0470 (7)	0.0327 (7)	−0.0031 (5)	−0.0081 (5)	−0.0161 (6)
O4	0.0210 (6)	0.0403 (7)	0.0447 (8)	−0.0034 (5)	−0.0037 (5)	−0.0148 (6)
O5	0.0312 (7)	0.0328 (6)	0.0264 (6)	−0.0123 (5)	−0.0051 (5)	0.0017 (5)
O6	0.0447 (8)	0.0431 (7)	0.0380 (7)	−0.0232 (6)	−0.0180 (6)	0.0053 (6)
O7	0.0271 (7)	0.0293 (6)	0.0322 (7)	−0.0064 (5)	−0.0012 (5)	−0.0087 (5)
O8	0.0322 (7)	0.0347 (7)	0.0434 (8)	−0.0031 (5)	−0.0086 (6)	−0.0102 (6)
N1	0.0412 (9)	0.0399 (9)	0.0286 (9)	−0.0012 (7)	−0.0027 (7)	−0.0093 (7)
N2	0.0214 (7)	0.0214 (6)	0.0224 (7)	−0.0027 (5)	−0.0019 (5)	−0.0035 (5)
C1	0.0206 (8)	0.0256 (8)	0.0258 (8)	−0.0073 (6)	−0.0030 (6)	−0.0056 (7)
C2	0.0214 (8)	0.0245 (8)	0.0242 (8)	−0.0071 (6)	−0.0057 (6)	−0.0041 (7)
C3	0.0251 (8)	0.0302 (8)	0.0259 (9)	−0.0097 (7)	−0.0032 (7)	−0.0077 (7)
C4	0.0327 (9)	0.0284 (8)	0.0248 (9)	−0.0100 (7)	−0.0094 (7)	0.0017 (7)
C5	0.0307 (9)	0.0238 (8)	0.034 (1)	−0.0065 (7)	−0.0102 (7)	−0.0014 (7)
C6	0.0259 (8)	0.0248 (8)	0.0319 (9)	−0.0050 (6)	−0.0071 (7)	−0.0040 (7)
C7	0.0195 (8)	0.0249 (8)	0.0279 (9)	−0.0045 (6)	−0.0036 (6)	−0.0070 (7)
C8	0.0213 (8)	0.0259 (8)	0.0249 (8)	−0.0083 (6)	−0.0019 (6)	−0.0076 (7)
C9	0.0217 (8)	0.0224 (8)	0.0200 (8)	−0.0009 (6)	−0.0024 (6)	−0.0049 (6)
C10	0.0198 (8)	0.0240 (8)	0.0221 (8)	−0.0019 (6)	−0.0016 (6)	−0.0077 (6)
C11	0.0237 (8)	0.0231 (8)	0.0216 (8)	−0.0033 (6)	−0.0026 (6)	−0.0060 (7)
C12	0.0251 (8)	0.0253 (8)	0.0216 (8)	−0.0013 (6)	−0.0036 (6)	−0.0061 (6)
C13	0.0195 (8)	0.0298 (8)	0.0281 (9)	−0.0022 (6)	−0.0052 (7)	−0.0079 (7)
C14	0.0202 (8)	0.0259 (8)	0.0301 (9)	−0.0048 (6)	−0.0007 (6)	−0.0080 (7)
C15	0.0249 (9)	0.0228 (8)	0.0232 (8)	−0.0067 (6)	−0.0018 (6)	−0.0011 (7)
C16	0.0289 (9)	0.0241 (8)	0.0221 (8)	−0.0064 (6)	−0.0045 (7)	−0.0035 (7)

Geometric parameters (Å, º)

O1—C7	1.217 (2)	C1—C7	1.485 (2)
O2—C8	1.213 (2)	C2—C3	1.401 (2)
O3—C15	1.323 (2)	C2—C8	1.458 (2)
O3—H1	1.02 (3)	C3—C4	1.415 (2)
O4—C15	1.200 (2)	C4—C5	1.372 (2)
O5—C16	1.318 (2)	C4—H4	0.98
O5—H2	0.86 (2)	C5—C6	1.390 (2)
O6—C16	1.214 (2)	C5—H5	0.98
O7—H1O7	0.83 (2)	C6—H6	0.98
O7—H2O7	0.93 (2)	C9—C10	1.393 (2)
O8—H1O8	1.09 (3)	C9—C14	1.383 (2)
O8—H2O8	1.00 (3)	C10—C11	1.398 (2)
N1—C3	1.352 (2)	C10—C15	1.511 (2)
N1—H1N1	0.95 (2)	C11—C12	1.392 (2)
N1—H2N1	0.96 (2)	C11—C16	1.489 (2)
N2—C7	1.399 (2)	C12—C13	1.383 (2)
N2—C8	1.415 (2)	C12—H12	0.98
N2—C9	1.441 (2)	C13—C14	1.390 (2)
C1—C2	1.395 (2)	C13—H13	0.98
C1—C6	1.374 (2)	C14—H14	0.98
C15—O3—H1	112 (1)	O1—C7—C1	129.8 (1)
C16—O5—H2	108 (1)	N2—C7—C1	106.1 (1)
H1O7—O7—H2O7	99 (2)	O2—C8—N2	124.1 (1)
H1O8—O8—H2O8	112 (2)	O2—C8—C2	129.9 (1)
C3—N1—H1N1	118 (1)	N2—C8—C2	106.0 (1)
C3—N1—H2N1	118 (1)	N2—C9—C10	118.6 (1)
H1N1—N1—H2N1	121 (2)	N2—C9—C14	120.2 (1)
C7—N2—C8	111.1 (1)	C10—C9—C14	121.1 (1)
C7—N2—C9	124.4 (1)	C9—C10—C11	118.9 (1)
C8—N2—C9	124.5 (1)	C9—C10—C15	117.9 (1)
C2—C1—C6	123.0 (1)	C11—C10—C15	123.2 (1)
C2—C1—C7	107.6 (1)	C10—C11—C12	119.8 (1)
C6—C1—C7	129.4 (1)	C10—C11—C16	119.0 (1)
C1—C2—C3	121.2 (1)	C12—C11—C16	121.2 (1)
C1—C2—C8	109.1 (1)	C11—C12—C13	120.6 (1)
C3—C2—C8	129.7 (1)	C11—C12—H12	119.7
N1—C3—C2	122.6 (2)	C13—C12—H12	119.7
N1—C3—C4	122.2 (2)	C12—C13—C14	119.8 (1)
C2—C3—C4	115.2 (1)	C12—C13—H13	120.1
C3—C4—C5	122.2 (1)	C14—C13—H13	120.1
C3—C4—H4	118.9	C9—C14—C13	119.7 (1)
C5—C4—H4	118.9	C9—C14—H14	120.2
C4—C5—C6	122.2 (1)	C13—C14—H14	120.2
C4—C5—H5	118.9	O3—C15—O4	125.1 (1)
C6—C5—H5	118.9	O3—C15—C10	111.9 (1)
C1—C6—C5	116.1 (1)	O4—C15—C10	122.8 (1)
C1—C6—H6	121.9	O5—C16—O6	122.5 (1)
C5—C6—H6	121.9	O5—C16—C11	114.9 (1)
O1—C7—N2	124.1 (1)	O6—C16—C11	122.5 (1)
O1—C7—N2—C8	177.7 (1)	C1—C7—N2—C8	−1.8 (2)
O1—C7—N2—C9	−3.5 (2)	C1—C7—N2—C9	176.9 (1)
O1—C7—C1—C2	−179.6 (2)	C2—C1—C6—C5	−1.4 (2)
O1—C7—C1—C6	−0.4 (3)	C2—C3—C4—C5	−1.0 (2)
O2—C8—N2—C7	−175.9 (1)	C2—C8—N2—C7	2.9 (2)
O2—C8—N2—C9	5.4 (2)	C2—C8—N2—C9	−175.8 (1)
O2—C8—C2—C1	175.8 (1)	C3—C2—C1—C6	1.0 (2)
O2—C8—C2—C3	−2.4 (3)	C3—C2—C1—C7	−179.8 (1)
O3—C15—C10—C9	−88.0 (2)	C3—C4—C5—C6	0.6 (2)
O3—C15—C10—C11	93.4 (2)	C4—C3—C2—C8	178.2 (1)
O4—C15—C10—C9	87.3 (2)	C5—C6—C1—C7	179.6 (1)
O4—C15—C10—C11	−91.3 (2)	C6—C1—C2—C8	−177.4 (1)
O5—C16—C11—C10	171.4 (1)	C7—N2—C9—C10	−82.3 (2)
O5—C16—C11—C12	−8.6 (2)	C7—N2—C9—C14	98.4 (2)
O6—C16—C11—C10	−7.6 (2)	C7—C1—C2—C8	1.9 (2)
O6—C16—C11—C12	172.4 (2)	C8—N2—C9—C10	96.2 (2)
N1—C3—C2—C1	179.9 (1)	C8—N2—C9—C14	−83.0 (2)
N1—C3—C2—C8	−2.1 (3)	C9—C10—C11—C12	0.7 (2)
N1—C3—C4—C5	179.4 (2)	C9—C10—C11—C16	−179.3 (1)
N2—C7—C1—C2	−0.1 (2)	C9—C14—C13—C12	0.2 (2)
N2—C7—C1—C6	179.1 (1)	C10—C9—C14—C13	1.2 (2)
N2—C8—C2—C1	−2.9 (2)	C10—C11—C12—C13	0.7 (2)
N2—C8—C2—C3	178.9 (1)	C11—C10—C9—C14	−1.7 (2)
N2—C9—C10—C11	179.1 (1)	C11—C12—C13—C14	−1.2 (2)
N2—C9—C10—C15	0.4 (2)	C12—C11—C10—C15	179.3 (1)
N2—C9—C14—C13	−179.5 (1)	C13—C12—C11—C16	−179.3 (1)
C1—C2—C3—C4	0.2 (2)	C14—C9—C10—C15	179.7 (1)
C1—C6—C5—C4	0.6 (2)	C15—C10—C11—C16	−0.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O8	1.02 (3)	1.61 (3)	2.604 (2)	164 (2)
O8—H1O8···O2^i	1.09 (3)	1.68 (3)	2.764 (2)	175 (2)
O5—H2···O7^ii	0.86 (2)	1.75 (2)	2.602 (2)	169 (2)
O7—H2O7···O6	0.93 (2)	1.87 (2)	2.776 (2)	164 (2)
O7—H1O7···O1^iii	0.83 (2)	1.95 (2)	2.782 (2)	177 (2)
O8—H2O8···O7	1.00 (3)	1.98 (3)	2.884 (2)	150 (3)
N1—H1N1···O3^iv	0.95 (2)	2.29 (2)	3.059 (2)	137 (2)
N1—H2N1···O5^v	0.96 (2)	2.45 (2)	3.289 (2)	147 (2)
N1—H1N1···O2	0.95 (2)	2.41 (2)	3.077 (2)	127 (2)
C14—H14···O4^vi	0.98	2.39	3.118 (2)	131
C6—H6···O8^vii	0.98	2.48	3.408 (2)	157
C12—H12···O1^viii	0.98	2.55	3.285 (2)	132
C5—H5···O4^ix	0.98	2.57	3.363 (2)	139
C4—H4···O5^v	0.98	2.60	3.438 (2)	144
C13—H13···O6^vi	0.98	2.74	3.490 (2)	134

Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+3, −z; (iii) x, y+1, z; (iv) −x+1, −y+2, −z+1; (v) x, y−1, z+1; (vi) x−1, y, z; (vii) x, y−1, z; (viii) −x+1, −y+2, −z; (ix) −x+2, −y+1, −z+1.