Supramolecular structures of 2-cyano-3-di­methyl­amino-N-(4-methyl­phenyl)­acryl­amide and 2-cyano-3-di­methyl­amino-N-(2-methoxy­phenyl)­acryl­amide

In the title compounds, C₁₃H₁₅N₃O, (I), and C₁₃H₁₅N₃O₂, (II), the dihedral angles between the planes of the phenyl ring and the amide group are 4.1 (1) and 20.7 (1)°, respectively. The mol­ecules adopt a fully extended conformation, aided by intramolecular interactions. The molecular structures of (I) and (II) display different crystal packing and hydrogen-bonding networks.

S1. Comment

As part of our study of conformational analysis, crystallographic work on N-aromatic amide derivatives has been undertaken. These derivatives are analogs of the active metabolites of the immunosuppressive drug leflunomide, which are known to act, in part, by inhibiting the tyrosine kinase epidermal growth-factor receptor (EGFR; Mattar et al., 1993). EGFR is a membrane- associated tyrosine kinase, which serves as an endogenous negative regulator of apoptosis in breast cancer cells (Uckun et al., 1998). The present study reports the structures of two N-acrylamide compounds, (I) and (II), in order to examine the effects of substituents on the hydrogen-bonding system and on the crystal structure.

The dihedral angle between the planes of the phenyl ring and the amide group is 4.1 (1) and 20.7 (1)° for (I) and (II), respectively. The geometry of the amide group is comparable to that of silimar groups in acetanilides (Haisa et al., 1977). The C10—C11 [1.420 (2) Å in (I) and 1.419 (2) Å in (II)] and C11—N12 [1.148 (2) Å in (I) and 1.147 (2) Å in (II)] bond lengths agree with the expected Csp²—Csp [1.431 (14) Å] and Csp¹—N(1) [1.136 (10) Å] bond lengths, respectively (Allen et al., 1987). Similar observations have been noted in the crystal structures of the leflunomide metabolite analogs (Ghosh et al., 1999; Ghosh & Uckun, 1999) and in the acrylamide derivative (Ompraba et al., 2003). In (II), the C2—O17—C18 [118.3 (1)°] angle is close to that expected for sp² hybridization of atom O17. The distortion and enlargement of the C6—C1—N7, C1—N7—C8 and N7—C8—O9 angles from the trigonal value (120°) are due to the intramolecular C6—H6···O9 hydrogen bond (Table 2 and 4). In both (I) and (II), the cyanoacrylamide side chain is planar, with π-conjugation along the chain causing variations of the bond distances with respect to the localized double and single bonds. The C1—N7—C8—C10 torsion angle does not differ much between (I) and (II) [−178.9 (1) and 176.6 (1)°, respectively], whereas the C6—C1—N7—C8 angle differs significantly [−3.7 (3) and −20.2 (2), respectively], indicating that the large twist around the C1—N7 bond in (II) is due to an intramolecular N7—H7···O17 hydrogen bond. This hydrogen bond determines the orientation of the methoxy group [C1—C2—O17—C18 = 179.5 (1)°], which is coplanar with the phenyl ring.

The supramolecular structures of (I) and (II) are completely different. In (I), the symmetry-related molecules are linked together head-to-tail via N7—H7··· N12 hydrogen bonds to form a dimer comprising an R²₂(12) ring (Bernstein et al., 1995). The dimers at (x, 1/2 − y, 1/2 + z), (2 − x, 1/2 + y, 1/2 − z) [centre of symmetry at (1, 1/2, 1/2)], and (x, 1/2 − y, −1/2 + z), (2 − x, 1/2 + y, −1/2 − z) [centre of symmetry at (1, 1/2, −1/2)] are further linked by symmetry-related C—H···O hydrogen bonds, involving atom O9 at (x, y, z) with atom H15A at (x, 1/2 − y, 1/2 + z), atom H15A at (x, y, z) with atom O9 at (x, 1/2 − y, −1/2 + z), atom O9 at (2 − x, 1 − y, −z) with atom H15A at (2 − x, 1/2 + y, −1/2 − z), and atom H15A at (2 − x, 1 − y, −z) with atom O9 at (2 − x, 1/2 + y, 1/2 − z), respectively, thus forming an R⁶₆(36) ring. Hence, a discrete hexamer is formed and related to it by a centre of symmetry at (1, 1/2, 0) (Fig. 3). The result is a two-dimensional layer, which runs along the bc plane (Fig. 4). In (II), an intramolecular N7—H7···O17 hydrogen bond forms a five-membered ring. A C(8) motif is formed via a C4—H4···O9(1 − x, 1/2 + y, 3/2 − z) hydrogen bond, creating a chain that runs parallel to the ab plane. Two such anti-parallel chains are shown in Fig. 5. In (II), a C—H···π interaction is also observed (Table 4). The H7···C11 distances, 2.34 Å in (I) and 2.28 Å in (II), are short as a result of the positive charge on atom H7 and negative charge on atom C11.

S2. Experimental

Substituted N-aryl cyano acetamide (0.005 mol) was dissolved in dimethyl formamide (6 ml) and kept in ice-cold conditions. To this solution, POCl₃ (1.4 ml, 0.015 mol) was added slowly with stirring. The reaction mixture was allowed to attain room temperature and stirred for 3–4 h. The residue was then poured into crushed ice and neutralized with 10% NaOH. The crude product obtained was filtered, washed with water and dried. Finally, the compound was purified by recrystallization using an ethylacetate–petroleum mixture. [m.p. 445 and 425 K for (I) and (II), respectively.]

S3. Refinement

All H atoms were fixed geometrically and allowed to ride on the corresponding non-H atoms.

Computing details

For both compounds, data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 35% probability level.
	Fig. 2. The molecular structure of (II), showing displacement ellipsoids at the 35% probability level.
	Fig. 3. A view of the discrete hexamer formed by the molecules of (I). [Symmetry codes: (i) x, 1/2 − y, 1/2 + z; (ii) x, 1/2 − y, −1/2 + z; (iii) 2 − x, 1/2 + y, 1/2 − z; (iv) 2 − x, 1/2 + y, −1/2 − z; (v) 2 − x, 1 − y, −z.]
	Fig. 4. The molecular packing of (I), viewed along the c axis.
	Fig. 5. A view of the crystal structure of (II), viewed along the a axis, showing two anti-parallel C(8) chains. [Symmetry code: (i) 1 − x, 1/2 + y, 3/2 − z.]

(I) 2-Cyano-3-dimethylamino-N-(4-methylphenyl) acrylamide

Crystal data

C13H15N3O	F(000) = 488
Mr = 229.28	Dx = 1.226 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.5846 (3) Å	Cell parameters from 4951 reflections
b = 22.4477 (10) Å	θ = 1.8–28.3°
c = 7.5989 (3) Å	µ = 0.08 mm^−1
β = 106.306 (1)°	T = 293 K
V = 1241.72 (9) Å^3	Slab, pale yellow
Z = 4	0.48 × 0.40 × 0.16 mm

Data collection

Siemens SMART CCD area detector diffractometer	2242 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 28.3°, θmin = 1.8°
ω scans	h = −10→8
8417 measured reflections	k = −29→27
3022 independent reflections	l = −10→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0849P)^2 + 0.2309P] where P = (Fo^2 + 2Fc^2)/3
3022 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.15 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 (Ų)

	x	y	z	Uiso*/Ueq
C1	1.0150 (2)	0.12001 (7)	0.3809 (2)	0.0450 (4)
C2	1.1069 (3)	0.07426 (8)	0.4941 (3)	0.0568 (4)
H2	1.1120	0.0365	0.4453	0.068*
C3	1.1906 (3)	0.08434 (9)	0.6780 (3)	0.0611 (5)
H3	1.2513	0.0532	0.7508	0.073*
C4	1.1860 (2)	0.13988 (8)	0.7565 (2)	0.0543 (4)
C5	1.0939 (3)	0.18476 (8)	0.6426 (3)	0.0575 (4)
H5	1.0890	0.2224	0.6919	0.069*
C6	1.0085 (2)	0.17584 (8)	0.4579 (2)	0.0532 (4)
H6	0.9471	0.2071	0.3858	0.064*
N7	0.93245 (19)	0.10564 (6)	0.19459 (19)	0.0506 (4)
H7	0.9520	0.0701	0.1620	0.061*
C8	0.8259 (2)	0.14088 (7)	0.0601 (2)	0.0475 (4)
O9	0.7881 (2)	0.19256 (6)	0.08790 (19)	0.0715 (4)
C10	0.7555 (2)	0.11279 (7)	−0.1227 (2)	0.0461 (4)
C11	0.7769 (3)	0.05031 (8)	−0.1381 (2)	0.0565 (4)
N12	0.7977 (3)	−0.00029 (8)	−0.1408 (3)	0.0860 (6)
C13	0.6724 (2)	0.15030 (7)	−0.2654 (2)	0.0473 (4)
H13	0.6702	0.1900	−0.2312	0.057*
N14	0.59520 (19)	0.14039 (6)	−0.44143 (19)	0.0499 (4)
C15	0.5150 (3)	0.18950 (9)	−0.5640 (3)	0.0656 (5)
H15A	0.5386	0.2264	−0.4976	0.098*
H15B	0.3848	0.1836	−0.6107	0.098*
H15C	0.5689	0.1907	−0.6641	0.098*
C16	0.5832 (3)	0.08205 (9)	−0.5273 (3)	0.0656 (5)
H16A	0.7036	0.0693	−0.5288	0.098*
H16B	0.5049	0.0844	−0.6507	0.098*
H16C	0.5331	0.0540	−0.4590	0.098*
C17	1.2781 (3)	0.15063 (11)	0.9576 (3)	0.0713 (6)
H17A	1.4035	0.1622	0.9739	0.107*
H17B	1.2745	0.1148	1.0253	0.107*
H17C	1.2147	0.1818	1.0015	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0454 (8)	0.0449 (8)	0.0447 (9)	−0.0026 (6)	0.0127 (6)	−0.0019 (6)
C2	0.0666 (11)	0.0461 (9)	0.0536 (10)	0.0036 (8)	0.0101 (8)	−0.0017 (7)
C3	0.0664 (11)	0.0617 (11)	0.0510 (10)	0.0052 (9)	0.0094 (8)	0.0067 (8)
C4	0.0508 (9)	0.0664 (11)	0.0460 (9)	−0.0104 (8)	0.0140 (7)	−0.0036 (8)
C5	0.0670 (11)	0.0532 (10)	0.0521 (10)	−0.0052 (8)	0.0163 (8)	−0.0098 (8)
C6	0.0601 (10)	0.0460 (9)	0.0513 (9)	0.0004 (7)	0.0120 (8)	−0.0020 (7)
N7	0.0606 (8)	0.0417 (7)	0.0457 (8)	0.0052 (6)	0.0086 (6)	−0.0038 (6)
C8	0.0486 (8)	0.0430 (8)	0.0489 (9)	0.0007 (6)	0.0104 (7)	−0.0026 (7)
O9	0.0930 (10)	0.0484 (7)	0.0575 (8)	0.0185 (6)	−0.0043 (7)	−0.0096 (6)
C10	0.0474 (8)	0.0413 (8)	0.0481 (9)	−0.0002 (6)	0.0111 (7)	−0.0035 (6)
C11	0.0661 (11)	0.0479 (9)	0.0487 (9)	0.0038 (8)	0.0051 (8)	−0.0052 (7)
N12	0.1270 (17)	0.0518 (10)	0.0645 (11)	0.0132 (10)	0.0026 (11)	−0.0068 (8)
C13	0.0472 (8)	0.0436 (8)	0.0488 (9)	−0.0030 (6)	0.0095 (7)	−0.0040 (7)
N14	0.0512 (8)	0.0475 (7)	0.0470 (8)	−0.0036 (6)	0.0075 (6)	−0.0023 (6)
C15	0.0744 (12)	0.0572 (11)	0.0552 (11)	−0.0030 (9)	0.0017 (9)	0.0055 (9)
C16	0.0754 (13)	0.0580 (11)	0.0566 (11)	−0.0008 (9)	0.0075 (9)	−0.0120 (8)
C17	0.0735 (13)	0.0897 (15)	0.0473 (10)	−0.0133 (11)	0.0114 (9)	−0.0043 (10)

Geometric parameters (Å, º)

C1—C6	1.390 (2)	C10—C13	1.378 (2)
C1—C2	1.394 (2)	C10—C11	1.420 (2)
C1—N7	1.415 (2)	C11—N12	1.148 (2)
C2—C3	1.381 (3)	C13—N14	1.320 (2)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.387 (3)	N14—C16	1.455 (2)
C3—H3	0.9300	N14—C15	1.461 (2)
C4—C5	1.383 (3)	C15—H15A	0.9600
C4—C17	1.511 (3)	C15—H15B	0.9600
C5—C6	1.385 (3)	C15—H15C	0.9600
C5—H5	0.9300	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
N7—C8	1.364 (2)	C16—H16C	0.9600
N7—H7	0.8600	C17—H17A	0.9600
C8—O9	1.228 (2)	C17—H17B	0.9600
C8—C10	1.482 (2)	C17—H17C	0.9600
C6—C1—C2	118.4 (2)	C11—C10—C8	118.6 (2)
C6—C1—N7	124.6 (2)	N12—C11—C10	176.4 (2)
C2—C1—N7	117.0 (1)	N14—C13—C10	132.0 (2)
C3—C2—C1	120.8 (2)	N14—C13—H13	114.0
C3—C2—H2	119.6	C10—C13—H13	114.0
C1—C2—H2	119.6	C13—N14—C16	124.1 (2)
C2—C3—C4	121.5 (2)	C13—N14—C15	120.4 (2)
C2—C3—H3	119.2	C16—N14—C15	115.5 (2)
C4—C3—H3	119.2	N14—C15—H15A	109.5
C5—C4—C3	117.0 (2)	N14—C15—H15B	109.5
C5—C4—C17	121.7 (2)	H15A—C15—H15B	109.5
C3—C4—C17	121.3 (2)	N14—C15—H15C	109.5
C4—C5—C6	122.6 (2)	H15A—C15—H15C	109.5
C4—C5—H5	118.7	H15B—C15—H15C	109.5
C6—C5—H5	118.7	N14—C16—H16A	109.5
C5—C6—C1	119.7 (2)	N14—C16—H16B	109.5
C5—C6—H6	120.2	H16A—C16—H16B	109.5
C1—C6—H6	120.2	N14—C16—H16C	109.5
C8—N7—C1	128.4 (1)	H16A—C16—H16C	109.5
C8—N7—H7	115.8	H16B—C16—H16C	109.5
C1—N7—H7	115.8	C4—C17—H17A	109.5
O9—C8—N7	122.5 (2)	C4—C17—H17B	109.5
O9—C8—C10	121.6 (2)	H17A—C17—H17B	109.5
N7—C8—C10	116.0 (1)	C4—C17—H17C	109.5
C13—C10—C11	125.2 (2)	H17A—C17—H17C	109.5
C13—C10—C8	116.3 (1)	H17B—C17—H17C	109.5
C6—C1—C2—C3	−0.5 (3)	C1—N7—C8—O9	0.3 (3)
N7—C1—C2—C3	−179.7 (2)	C1—N7—C8—C10	−178.9 (1)
C1—C2—C3—C4	0.1 (3)	O9—C8—C10—C13	10.6 (2)
C2—C3—C4—C5	0.0 (3)	N7—C8—C10—C13	−170.2 (1)
C2—C3—C4—C17	−179.9 (2)	O9—C8—C10—C11	−169.1 (2)
C3—C4—C5—C6	0.1 (3)	N7—C8—C10—C11	10.1 (2)
C17—C4—C5—C6	−180.0 (2)	C13—C10—C11—N12	−174 (4)
C4—C5—C6—C1	−0.4 (3)	C8—C10—C11—N12	6 (4)
C2—C1—C6—C5	0.6 (3)	C11—C10—C13—N14	0.1 (3)
N7—C1—C6—C5	179.7 (2)	C8—C10—C13—N14	−179.5 (2)
C6—C1—N7—C8	−3.7 (3)	C10—C13—N14—C16	−0.5 (3)
C2—C1—N7—C8	175.4 (2)	C10—C13—N14—C15	179.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O9	0.93	2.27	2.864 (2)	121
C13—H13···O9	0.93	2.34	2.748 (2)	106
N7—H7···N12^i	0.86	2.50	3.228 (2)	143
C15—H15A···O9^ii	0.96	2.57	3.360 (2)	139

Symmetry codes: (i) −x+2, −y, −z; (ii) x, −y+1/2, z−1/2.

(II) 2-cyano-3-dimethylamino-N-(2-methoxyphenyl) acrylamide

Crystal data

C13H15N3O2	F(000) = 520
Mr = 245.28	Dx = 1.221 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.5141 (3) Å	Cell parameters from 5915 reflections
b = 12.7580 (6) Å	θ = 2.2–28.3°
c = 13.9381 (6) Å	µ = 0.09 mm^−1
β = 92.795 (1)°	T = 293 K
V = 1334.58 (10) Å^3	Block, pale yellow
Z = 4	0.48 × 0.46 × 0.42 mm

Data collection

Siemens SMART CCD area detector diffractometer	2425 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.041
Graphite monochromator	θmax = 28.3°, θmin = 2.2°
ω scans	h = −9→9
9025 measured reflections	k = −16→16
3278 independent reflections	l = −12→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0825P)^2 + 0.0796P] where P = (Fo^2 + 2Fc^2)/3
3278 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.14 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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.32342 (17)	0.33713 (10)	0.59837 (10)	0.0514 (3)
C2	0.31085 (17)	0.44491 (10)	0.57594 (11)	0.0542 (3)
C3	0.3823 (2)	0.51814 (12)	0.64002 (13)	0.0686 (4)
H3	0.3737	0.5893	0.6259	0.082*
C4	0.4662 (2)	0.48520 (14)	0.72487 (14)	0.0786 (5)
H4	0.5155	0.5347	0.7674	0.094*
C5	0.4784 (2)	0.38067 (15)	0.74779 (13)	0.0762 (5)
H5	0.5351	0.3598	0.8054	0.091*
C6	0.4055 (2)	0.30611 (12)	0.68437 (11)	0.0645 (4)
H6	0.4122	0.2353	0.7000	0.077*
N7	0.24551 (16)	0.26844 (8)	0.52943 (8)	0.0566 (3)
H7	0.1688	0.2959	0.4891	0.068*
C8	0.27600 (17)	0.16353 (9)	0.51832 (9)	0.0492 (3)
O9	0.38642 (16)	0.11575 (8)	0.56936 (8)	0.0743 (4)
C10	0.16552 (17)	0.11172 (9)	0.44245 (9)	0.0471 (3)
C11	0.0296 (2)	0.17190 (10)	0.39442 (11)	0.0639 (4)
N12	−0.0784 (3)	0.22659 (12)	0.36191 (14)	0.1057 (7)
C13	0.19887 (17)	0.00661 (9)	0.42685 (9)	0.0476 (3)
H13	0.2888	−0.0219	0.4670	0.057*
N14	0.12454 (15)	−0.05982 (8)	0.36472 (8)	0.0521 (3)
C15	0.1804 (2)	−0.16950 (10)	0.36508 (13)	0.0671 (4)
H15A	0.2757	−0.1794	0.4126	0.101*
H15B	0.2207	−0.1878	0.3029	0.101*
H15C	0.0816	−0.2133	0.3799	0.101*
C16	−0.0130 (2)	−0.03100 (13)	0.29272 (13)	0.0745 (5)
H16A	−0.1197	−0.0123	0.3238	0.112*
H16B	−0.0370	−0.0893	0.2505	0.112*
H16C	0.0268	0.0276	0.2563	0.112*
O17	0.22428 (14)	0.46702 (7)	0.48990 (8)	0.0645 (3)
C18	0.2047 (2)	0.57396 (11)	0.46233 (14)	0.0724 (5)
H18A	0.1467	0.6118	0.5115	0.109*
H18B	0.1342	0.5783	0.4032	0.109*
H18C	0.3201	0.6039	0.4537	0.109*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0465 (7)	0.0457 (6)	0.0620 (7)	0.0014 (5)	0.0036 (5)	−0.0108 (5)
C2	0.0442 (7)	0.0436 (6)	0.0753 (9)	0.0007 (5)	0.0089 (6)	−0.0125 (6)
C3	0.0609 (9)	0.0505 (8)	0.0946 (12)	−0.0020 (6)	0.0049 (8)	−0.0247 (7)
C4	0.0679 (10)	0.0749 (11)	0.0926 (12)	−0.0002 (8)	−0.0004 (9)	−0.0392 (9)
C5	0.0696 (10)	0.0911 (12)	0.0671 (9)	0.0083 (8)	−0.0058 (8)	−0.0230 (8)
C6	0.0660 (9)	0.0611 (8)	0.0660 (9)	0.0059 (7)	−0.0010 (7)	−0.0100 (7)
N7	0.0639 (7)	0.0383 (5)	0.0660 (7)	0.0039 (5)	−0.0128 (5)	−0.0045 (5)
C8	0.0531 (7)	0.0395 (6)	0.0544 (7)	0.0044 (5)	−0.0024 (5)	0.0001 (5)
O9	0.0849 (8)	0.0514 (5)	0.0830 (7)	0.0174 (5)	−0.0334 (6)	−0.0094 (5)
C10	0.0536 (7)	0.0380 (5)	0.0495 (6)	0.0035 (5)	−0.0016 (5)	0.0014 (4)
C11	0.0839 (10)	0.0435 (7)	0.0620 (8)	0.0099 (6)	−0.0207 (7)	−0.0050 (6)
N12	0.1331 (15)	0.0691 (9)	0.1086 (12)	0.0380 (9)	−0.0599 (11)	−0.0161 (8)
C13	0.0520 (7)	0.0403 (6)	0.0503 (6)	0.0022 (5)	0.0001 (5)	0.0019 (5)
N14	0.0573 (6)	0.0398 (5)	0.0588 (6)	0.0007 (4)	−0.0010 (5)	−0.0039 (4)
C15	0.0752 (10)	0.0398 (7)	0.0858 (10)	0.0011 (6)	−0.0020 (8)	−0.0093 (6)
C16	0.0795 (11)	0.0659 (9)	0.0757 (10)	0.0080 (8)	−0.0216 (8)	−0.0143 (8)
O17	0.0706 (6)	0.0385 (5)	0.0837 (7)	0.0012 (4)	−0.0037 (5)	−0.0012 (4)
C18	0.0725 (10)	0.0397 (7)	0.1056 (13)	0.0046 (6)	0.0093 (9)	0.0032 (7)

Geometric parameters (Å, º)

C1—C6	1.379 (2)	C10—C11	1.419 (2)
C1—N7	1.407 (2)	C11—N12	1.147 (2)
C1—C2	1.412 (2)	C13—N14	1.316 (2)
C2—O17	1.366 (2)	C13—H13	0.9300
C2—C3	1.383 (2)	N14—C16	1.452 (2)
C3—C4	1.379 (3)	N14—C15	1.461 (2)
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.373 (3)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—C6	1.392 (2)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
N7—C8	1.368 (2)	O17—C18	1.423 (2)
N7—H7	0.8600	C18—H18A	0.9600
C8—O9	1.228 (2)	C18—H18B	0.9600
C8—C10	1.469 (2)	C18—H18C	0.9600
C10—C13	1.383 (2)
C6—C1—N7	124.6 (1)	N12—C11—C10	174.1 (2)
C6—C1—C2	119.6 (1)	N14—C13—C10	130.8 (1)
N7—C1—C2	115.7 (1)	N14—C13—H13	114.6
O17—C2—C3	125.5 (1)	C10—C13—H13	114.6
O17—C2—C1	114.8 (1)	C13—N14—C16	123.8 (1)
C3—C2—C1	119.7 (2)	C13—N14—C15	120.1 (1)
C4—C3—C2	119.7 (2)	C16—N14—C15	116.1 (1)
C4—C3—H3	120.2	N14—C15—H15A	109.5
C2—C3—H3	120.2	N14—C15—H15B	109.5
C5—C4—C3	121.2 (2)	H15A—C15—H15B	109.5
C5—C4—H4	119.4	N14—C15—H15C	109.5
C3—C4—H4	119.4	H15A—C15—H15C	109.5
C4—C5—C6	119.7 (2)	H15B—C15—H15C	109.5
C4—C5—H5	120.1	N14—C16—H16A	109.5
C6—C5—H5	120.1	N14—C16—H16B	109.5
C1—C6—C5	120.1 (2)	H16A—C16—H16B	109.5
C1—C6—H6	120.0	N14—C16—H16C	109.5
C5—C6—H6	120.0	H16A—C16—H16C	109.5
C8—N7—C1	128.4 (1)	H16B—C16—H16C	109.5
C8—N7—H7	115.8	C2—O17—C18	118.3 (1)
C1—N7—H7	115.8	O17—C18—H18A	109.5
O9—C8—N7	122.2 (1)	O17—C18—H18B	109.5
O9—C8—C10	122.4 (1)	H18A—C18—H18B	109.5
N7—C8—C10	115.5 (1)	O17—C18—H18C	109.5
C13—C10—C11	125.6 (1)	H18A—C18—H18C	109.5
C13—C10—C8	116.7 (1)	H18B—C18—H18C	109.5
C11—C10—C8	117.7 (1)
C6—C1—C2—O17	−178.9 (1)	C1—N7—C8—C10	176.6 (1)
N7—C1—C2—O17	−0.0 (2)	O9—C8—C10—C13	−3.8 (2)
C6—C1—C2—C3	0.5 (2)	N7—C8—C10—C13	177.3 (1)
N7—C1—C2—C3	179.4 (1)	O9—C8—C10—C11	173.6 (2)
O17—C2—C3—C4	179.8 (1)	N7—C8—C10—C11	−5.3 (2)
C1—C2—C3—C4	0.5 (2)	C13—C10—C11—N12	162 (2)
C2—C3—C4—C5	−0.9 (2)	C8—C10—C11—N12	−15 (2)
C3—C4—C5—C6	0.2 (3)	C11—C10—C13—N14	3.4 (2)
N7—C1—C6—C5	−179.9 (1)	C8—C10—C13—N14	−179.4 (1)
C2—C1—C6—C5	−1.2 (2)	C10—C13—N14—C16	2.7 (2)
C4—C5—C6—C1	0.8 (2)	C10—C13—N14—C15	−177.8 (1)
C6—C1—N7—C8	−20.2 (2)	C3—C2—O17—C18	0.1 (2)
C2—C1—N7—C8	161.0 (1)	C1—C2—O17—C18	179.5 (1)
C1—N7—C8—O9	−2.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O9	0.93	2.38	2.910 (2)	116
C13—H13···O9	0.93	2.36	2.756 (2)	106
N7—H7···O17	0.86	2.22	2.596 (1)	106
C4—H4···O9^i	0.93	2.57	3.452 (2)	158
C18—H18C···Cg^ii	0.96	2.75	3.551 (1)	141

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+1.