C—halogen...π dimer and C—H...π interactions in 1-(2-bromo-4,5-di­meth­oxy­benzyl)-2-butyl-4-chloro-1H-imidazole-5-carbaldehyde and 2-butyl-4-chloro-1-(6-methyl-1,3-benzodioxol-5-ylmethyl)-1H-imidazole-5-carbaldehyde

The structures of the title compounds, C₁₇H₂₀BrClN₂O₃, (I), and C₁₇H₁₉ClN₂O₃, (II), are stabilized by intramolecular C—H...O and C—H...π interactions. The stability of the molecular packing in (I) and (II) arises from a diverse set of weak intermolecular C—H...O, C—H...π and C—halogen...π interactions. In the crystal structure of (I), mol­ecules aggregate in dimeric subunits via C—Br...π interactions. The dimers are interlinked by C—H...O hydrogen bonds. The halogens cluster together and form a channel along the b axis. In (II), the packing is mainly governed by intermolecular C—H...O and C—H...π interactions.

S1. Comment

The molecular assembly in a crystal is predominantly governed by intermolecular forces, conventionally described by strong and directional N—H···O, O—H···O and O—H···N hydrogen-bonds (Desiraju, 2002). In molecules having an imbalance of hydrogen-bond donors and acceptors, the deficiency in either donor or acceptor is fulfilled by other types of weak and less-directional forces. Interactions involving the π cloud in aromatic compounds also belong to this category. The presence of several types of aromatic, X—H···π, X—halogen (Hal)···π and π–π interactions have been established and characterized in many different molecular systems (Desiraju & Steiner, 1999; Desiraju, 2002). The motivation for understanding these interaction arises from their potential importance in generating supramolecular architectures for the design of molecular solids with novel properties. Organic molecules with such characteristics provide an excellent means of exploring the roles of non-conventional intermolecular forces in crystal engineering and supramolecular chemistry. In the present work, we report the syntheses and structures of two imidazole derivatives, and discuss the relevance of weak intermolecular interactions in molecular packing. The title compounds, (I) and (II), are intermediates in the synthesis of biologically active isoxazoles and isoxazoline (Pruitt et al., 2000).

In the crystal structure, the planar moieties are formed by group of atoms attached to the aromatic imidazole (Imd) ring, namely atoms C1–C4, C8, C9, Cl1, N1 and N2 in both (I) and (II), and to the phenyl (Ph) ring, i.e. atoms C9–C17, O2 and O3 in (II) and atoms C9–C17, O2, O3 and Br1 in (I). The dihedral angles between these planar groups are 82.8 (1) and 85.5 (1)° in (I) and (II), respectively. The overall structures of (I) and (II) can be inferred from the ellipsoid plots shown in Fig. 1. The molecular conformation is essentially gauche about the N2—C9 bond and trans about the C9—C10 bond. The C1—N2—C9—C10 torsion angle is 105.2 (4)° in (I) and 93.9 (2)° in (II), and the N2—C9—C10—C11 angle is 164.5 (3) and 172.30 (18)° in (I) and (II), respectively. The sign of the torsion angle, which otherwise has no meaning for centrosymmetric crystals, corresponds to the reported coordinates of the structure. The non-planar part of the molecules, i.e. the butyl chain attached to the imidazole ring, is characterized by the N1—C1—C4—C5, C1—C4—C5—C6 and C4—C5—C6—C7 torsion angles. These angles are −15.6 (10), −176.9 (7) and 97.6 (10)° in (I), and −4.2 (3), 174.3 (2) and −176.4 (3)° in (II), indicating that the conformation of butyl-chain is bent in (I) and fully extended in (II). The geometric parameters for the inter- and intramolecular interactions are given in Tables 1 and 2. The molecular structures are primarily stabilized by intramolecular C15—H15···π(Imd) and C9—H9B···O1 interactions. The C9—H9B···O1 contact forms an S₆ hydrogen-bonded pattern (Bernstein et al., 1995) in both molecules. As observed in a similar compound (Gaonkar et al., 2004), and the very few related structures found in the Cambridge Structural Database (CSD; Allen, 2002), these two interactions appear to play a predominant role in shaping the molecular structure.

The crystal packing is described by a diverse set of weak intermolecular interactions (Tables 1 and 2). The molecules of (I) and (II) contain no amino donor atoms. This deficiency is partially compensated by interactions involving halogen atoms and the aromatic rings. Short intermolecular C—Hal···π contacts stabilize the dimeric subunits in (I) (Fig 2). A dimer is formed by a C11—Br1···π(Imd)(−x + 1, −y, −z + 1) contact. The Br1···Cg1 distance (Cg1 is the centroid of the Imd ring) and C11—Br1···Cg1 angle are 3.857 (4) Å and 123.6 (2)°, respectively, whereas the minimum atomic distance, Br1···π, is 3.51 Å. The Br···π interaction is less well documented, among both small and macromolecules, than the F···π and Cl···π interactions (Prasanna & Guru Row, 2000; Saraogi et al., 2003). The average value of the minimum atomic distance in intermolecular C—Br···π contacts reported in the CSD is 3.625 (9) Å (Prasanna & Guru Row, 2000). The C—Hal···π dimer interactions, which have also been referred to as PHD (π–halogen-dimer) interactions, have recently been shown to play an important role in host–guest chemistry (Nomen et al., 2004). The dimeric subunits are interlinked by intermolecular a C16—H16A···O1 contact, contributing further to the stability of the crystal packing. In the crystal structure, the halogen atoms, Cl and Br, cluster together and form a channel along the b axis. The closest Hal···Hal contacts were Cl1···Cl1(−x + 2,-y + 1,-z + 1) [3.503 (2) Å] and Cl1···Br1(−x + 1,-y,-z + 1) [3.555 (6) Å]. However, the halogen atoms fail to form a network similar to that reported for tetrakis(4-iodophenyl)methane (Thaimattam et al., 1998). It is not clear if such clustering is the result of characteristic intermolecular forces among halogens (Price et al., 1994). Packing in (II) is mainly governed by intermolecular C—H···O and C—H···π interactions other than van der Waals forces. These interactions were observed in the C9—H9A···O1 and C17—H17A···π(Ph) contacts (Table 2). The crystal packing of (II) is shown in Fig. 3.

In summary, the role of weak intermolecular interactions in the stability of the crystal packing in the two examples, which lack strong amine and O donor atoms, have been highlighted. The C—H···O, C—Hal···π and C—H···π interactions govern the packing in (I) and (II). The identification of such motifs signifies the importance of non-conventional weak intermolecular interactions in ordering the crystal packing arrangements. It will be of particular interest to examine the occurrences and roles of C—Hal···π dimer interactions in organic compounds.

S2. Experimental

Compound (I) was synthesized by condensing an equimolar mixture of 2-butyl-5-chloro-3H-imidazole-4-carboxaldehyde and 2-bromo-4,5-di-methoxybenzyl bromide with potassium carbonate in a dimethylformamide medium with stirring at room temperature for 10 h (yield, 90%, m.p. 360 K). Compound (II) was prepared by condensing an equimolar mixture of 2-butyl-5-chloro-3H-imidazole- 4-carboxaldehyde and 6-methyl-benzo[1,3]dioxol-5-ylmethyl chloride under the same conditions (yield, 90%, m.p. 385 K). The materials were recrystallized from acetonitrile.

S3. Refinement

The H atoms were refined with fixed geometry, riding on their carrier atoms with U_iso set at 1.2 (1.5 for the methyl H-atoms) U_eq of the parent atom (C—H = 0.95–0.99 Å). In (I), the Br atom is statistically disordered over two adjacent sites; the partial occupancies refined to 0.54 (4) and 0.46 (4). Atoms Br1 and Br2, which occupy the former and the latter positions, lie, respectively, −0.16 and 0.11 Å from the mean aromatic plane formed by atoms C10–C15. The C4—C5 bond length in (I) was restrained to 1.54 (1) Å because of thermal disorder.

Computing details

For both compounds, data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS86 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

Figures

	Fig. 1. ORTEP-3 plots of (a) (I) and (b) (II), in comparable orientations, with the atom-numbering schemes. Displacement ellipsoids are shown at the 30% probability level. H atoms are shown as small spheres of arbitrary radii and the dashed lines represent intramolecular C—H···O and C—H···π interactions. [In the online version of the journal, the color scheme for the atoms for all figures is as follows: C: black or gray; H: white; Br: yellow; Cl: green; N: blue; O: red.]
	Fig. 2. The crystal packing in (I), showing a chain of molecules along the [101] direction. For clarity intermolecular interactions are represented by dark dashed lines, whereas intramolecular interactions are shown as light dashed lines. The symbols * and # indicate atoms associated with molecules related by the symmetry operations (−x + 1, −y, −z + 1) and (−x, −y, −z), respectively.
	Fig. 3. The crystal packing in (II), showing a sheet structure formed by molecules about the (20–2) plane. The intermolecular contacts are represented by dashed lines. The symbols * and # refer to atoms associated with molecules related by the symmetry operations (−x + 1, −y + 1, −z) and (−x + 3/2, y + 1/2, −z + 1/2), respectively.

(I) 1-(2-bromo-4,5-dimethoxybenzyl)-2-butyl-4-chloro-1H-imidazole-5-carboxaldehyde

Crystal data

C17H20BrClN2O3	Z = 2
Mr = 415.72	F(000) = 424
Triclinic, P1	Dx = 1.507 Mg m^−3
Hall symbol: -P 1	Melting point: 360 K
a = 8.547 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.308 (2) Å	Cell parameters from 1017 reflections
c = 10.611 (2) Å	θ = 2.4–25.6°
α = 91.654 (4)°	µ = 2.41 mm^−1
β = 100.667 (4)°	T = 193 K
γ = 93.623 (3)°	Block, colorless
V = 916.2 (4) Å^3	0.14 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4087 independent reflections
Radiation source: fine-focus sealed tube	2655 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 28.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.73, Tmax = 0.79	k = −13→13
7830 measured reflections	l = −14→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.170	w = 1/[σ^2(Fo^2) + (0.0839P)^2 + 0.3943P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
4087 reflections	Δρmax = 0.88 e Å^−3
231 parameters	Δρmin = −0.66 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (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.

Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d

Plane 1 m1 = 0.75592(0.00099) m2 = −0.21347(0.00147) m3 = −0.61888(0.00115) D = −1.92240(0.00379) Atom d s d/s (d/s)**2 C10 * 0.0120 0.0032 3.715 13.804 C11 * −0.0120 0.0036 − 3.336 11.126 C12 * −0.0022 0.0037 − 0.597 0.356 C13 * 0.0126 0.0036 3.517 12.371 C14 * −0.0082 0.0034 − 2.423 5.872 C15 * −0.0035 0.0033 − 1.070 1.144 Br1 − 0.1604 0.0052 − 30.668 940.545 Br2 0.1073 0.0116 9.274 86.011 ============ Sum((d/s)**2) for starred atoms 44.673 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity

Plane 2 m1 = −0.45965(0.00053) m2 = 0.65546(0.00073) m3 = −0.59925(0.00099) D = −2.94159(0.00612) Atom d s d/s (d/s)**2 Cl1 * −0.0095 0.0015 − 6.452 41.634 N1 * 0.0237 0.0035 6.714 45.077 N2 * 0.0196 0.0028 7.036 49.510 C1 * 0.0025 0.0041 0.614 0.377 C2 * 0.0401 0.0035 11.331 128.397 C3 * 0.0516 0.0040 12.911 166.686 C8 * −0.0379 0.0049 − 7.813 61.050 C9 * −0.0354 0.0039 − 9.128 83.322 C4 * −0.1029 0.0062 − 16.550 273.918 O1 − 0.2160 0.0039 − 55.056 3031.110 C10 1.2996 0.0033 393.176 154587.703 ============ Sum((d/s)**2) for starred atoms 849.971 Chi-squared at 95% for 6 degrees of freedom: 12.60 The group of atoms deviates significantly from planarity

Plane 3 m1 = 0.76820(0.00047) m2 = −0.20680(0.00062) m3 = −0.60589(0.00053) D = −1.87715(0.00186) Atom d s d/s (d/s)**2 O2 * 0.0087 0.0030 2.905 8.441 O3 * −0.0189 0.0029 − 6.596 43.509 C9 * 0.0921 0.0039 23.913 571.818 C10 * 0.0308 0.0032 9.516 90.555 C11 * −0.0166 0.0036 − 4.603 21.189 C12 * −0.0296 0.0037 − 7.988 63.802 C13 * −0.0144 0.0036 − 4.034 16.277 C14 * −0.0117 0.0034 − 3.459 11.962 C15 * 0.0154 0.0033 4.674 21.849 C16 * 0.1249 0.0048 26.248 688.975 C17 * −0.0718 0.0049 − 14.534 211.246 Br1 * −0.1662 0.0052 − 32.132 1032.488 Br2 0.1000 0.0115 8.724 76.109 N2 0.4948 0.0027 182.023 33132.480 ============ Sum((d/s)**2) for starred atoms 2782.111 Chi-squared at 95% for 9 degrees of freedom: 16.90 The group of atoms deviates significantly from planarity

Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 83.31 (0.08) 96.69 (0.08) 1 3 1.09 (0.07) 178.91 (0.07) 2 3 82.79 (0.05) 97.21 (0.05)

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	Occ. (<1)
Br1	0.0700 (4)	−0.1262 (4)	0.3665 (7)	0.0788 (9)	0.54 (4)
Br2	0.0819 (9)	−0.1312 (4)	0.3440 (15)	0.0959 (15)	0.46 (4)
Cl1	0.83053 (15)	0.39614 (15)	0.44068 (14)	0.1025 (5)
O1	0.5146 (5)	0.0499 (4)	0.2644 (3)	0.1066 (13)
O2	−0.1722 (4)	0.2052 (3)	0.0256 (3)	0.0812 (9)
O3	0.0200 (3)	0.3958 (3)	0.1277 (3)	0.0719 (8)
N1	0.5973 (4)	0.3778 (3)	0.5747 (3)	0.0723 (9)
N2	0.4390 (3)	0.2127 (3)	0.4793 (3)	0.0512 (7)
C1	0.4662 (5)	0.3029 (4)	0.5763 (4)	0.0670 (11)
C2	0.5617 (4)	0.2294 (3)	0.4108 (3)	0.0552 (8)
C3	0.6535 (4)	0.3328 (4)	0.4741 (4)	0.0633 (10)
C4	0.3631 (6)	0.3078 (7)	0.6732 (5)	0.114 (2)
H4A	0.3331	0.2173	0.6928	0.137*
H4B	0.2638	0.3472	0.6342	0.137*
C5	0.4301 (8)	0.3802 (10)	0.7964 (5)	0.172 (4)
H5A	0.5322	0.3441	0.8340	0.207*
H5B	0.4541	0.4722	0.7782	0.207*
C6	0.3252 (9)	0.3762 (10)	0.8928 (6)	0.146 (3)
H6A	0.3338	0.4632	0.9366	0.175*
H6B	0.2135	0.3592	0.8471	0.175*
C7	0.3581 (14)	0.2809 (8)	0.9889 (10)	0.184 (5)
H7A	0.2811	0.2845	1.0466	0.276*
H7B	0.4664	0.2993	1.0383	0.276*
H7C	0.3492	0.1940	0.9471	0.276*
C8	0.5881 (6)	0.1491 (5)	0.3057 (4)	0.0795 (13)
H8	0.6730	0.1776	0.2644	0.095*
C9	0.3077 (4)	0.1116 (4)	0.4542 (4)	0.0631 (10)
H9A	0.2605	0.1031	0.5323	0.076*
H9B	0.3510	0.0275	0.4367	0.076*
C10	0.1769 (4)	0.1385 (3)	0.3419 (3)	0.0488 (8)
C11	0.0670 (4)	0.0400 (3)	0.2882 (4)	0.0550 (8)
C12	−0.0517 (4)	0.0570 (4)	0.1833 (4)	0.0619 (10)
H12	−0.1246	−0.0138	0.1480	0.074*
C13	−0.0632 (4)	0.1755 (4)	0.1313 (4)	0.0577 (9)
C14	0.0436 (4)	0.2812 (3)	0.1857 (3)	0.0525 (8)
C15	0.1617 (4)	0.2602 (3)	0.2896 (3)	0.0504 (8)
H15	0.2343	0.3308	0.3262	0.060*
C16	−0.2736 (5)	0.0993 (5)	−0.0395 (5)	0.0901 (15)
H16A	−0.3379	0.1296	−0.1180	0.135*
H16B	−0.3443	0.0652	0.0165	0.135*
H16C	−0.2083	0.0304	−0.0617	0.135*
C17	0.1186 (6)	0.5066 (4)	0.1806 (4)	0.0800 (13)
H17A	0.0885	0.5821	0.1298	0.120*
H17B	0.2303	0.4911	0.1795	0.120*
H17C	0.1055	0.5234	0.2693	0.120*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.054 (2)	0.080 (2)	0.0945 (16)	−0.0195 (6)	0.0002 (12)	0.0140 (9)
Br2	0.108 (3)	0.0490 (14)	0.111 (3)	−0.0190 (10)	−0.0227 (16)	0.0116 (11)
Cl1	0.0737 (7)	0.1256 (11)	0.1004 (10)	−0.0447 (7)	0.0133 (7)	0.0075 (8)
O1	0.103 (3)	0.113 (3)	0.091 (2)	−0.010 (2)	0.001 (2)	−0.049 (2)
O2	0.0664 (17)	0.0859 (19)	0.0706 (18)	−0.0042 (14)	−0.0359 (14)	−0.0105 (15)
O3	0.0709 (17)	0.0625 (15)	0.0666 (17)	−0.0052 (12)	−0.0238 (13)	0.0000 (12)
N1	0.0586 (18)	0.080 (2)	0.069 (2)	−0.0112 (16)	−0.0035 (17)	−0.0221 (17)
N2	0.0411 (14)	0.0628 (16)	0.0430 (15)	−0.0070 (12)	−0.0052 (12)	−0.0034 (12)
C1	0.050 (2)	0.094 (3)	0.049 (2)	−0.0032 (19)	−0.0043 (17)	−0.018 (2)
C2	0.0479 (18)	0.063 (2)	0.048 (2)	−0.0057 (15)	−0.0044 (15)	−0.0021 (16)
C3	0.0490 (19)	0.073 (2)	0.061 (2)	−0.0141 (17)	−0.0032 (17)	0.0028 (19)
C4	0.063 (3)	0.180 (6)	0.094 (4)	−0.007 (3)	0.015 (3)	−0.056 (4)
C5	0.079 (4)	0.368 (14)	0.068 (4)	0.003 (6)	0.017 (3)	−0.017 (5)
C6	0.103 (5)	0.254 (10)	0.083 (4)	0.001 (6)	0.030 (4)	−0.024 (5)
C7	0.274 (12)	0.129 (6)	0.197 (9)	0.014 (7)	0.171 (10)	0.007 (6)
C8	0.072 (3)	0.105 (3)	0.056 (3)	−0.001 (2)	0.003 (2)	−0.016 (2)
C9	0.0509 (19)	0.071 (2)	0.057 (2)	−0.0178 (17)	−0.0093 (16)	0.0063 (18)
C10	0.0375 (15)	0.0601 (18)	0.0446 (18)	−0.0062 (13)	0.0007 (13)	−0.0037 (15)
C11	0.0450 (17)	0.0546 (18)	0.060 (2)	−0.0055 (14)	−0.0017 (16)	−0.0007 (16)
C12	0.0447 (18)	0.064 (2)	0.067 (2)	−0.0115 (16)	−0.0064 (17)	−0.0188 (18)
C13	0.0379 (16)	0.070 (2)	0.055 (2)	−0.0037 (15)	−0.0104 (15)	−0.0157 (17)
C14	0.0446 (17)	0.0611 (19)	0.0449 (19)	−0.0040 (14)	−0.0056 (14)	−0.0083 (15)
C15	0.0430 (16)	0.0579 (18)	0.0440 (18)	−0.0096 (14)	−0.0020 (14)	−0.0093 (14)
C16	0.066 (3)	0.103 (3)	0.080 (3)	−0.005 (2)	−0.031 (2)	−0.034 (3)
C17	0.089 (3)	0.060 (2)	0.075 (3)	−0.013 (2)	−0.017 (2)	−0.003 (2)

Geometric parameters (Å, º)

Br1—C11	1.925 (5)	C6—H6A	0.9900
Br2—C11	1.883 (5)	C6—H6B	0.9900
Cl1—C3	1.712 (4)	C7—H7A	0.9800
O1—C8	1.193 (6)	C7—H7B	0.9800
O2—C13	1.375 (4)	C7—H7C	0.9800
O2—C16	1.427 (5)	C8—H8	0.9500
O3—C14	1.357 (4)	C9—C10	1.521 (5)
O3—C17	1.413 (5)	C9—H9A	0.9900
N1—C1	1.323 (5)	C9—H9B	0.9900
N1—C3	1.332 (5)	C10—C11	1.374 (4)
N2—C1	1.345 (5)	C10—C15	1.390 (5)
N2—C2	1.387 (5)	C11—C12	1.383 (5)
N2—C9	1.463 (4)	C12—C13	1.357 (6)
C1—C4	1.474 (7)	C12—H12	0.9500
C2—C3	1.364 (5)	C13—C14	1.412 (5)
C2—C8	1.430 (6)	C14—C15	1.382 (5)
C4—C5	1.486 (4)	C15—H15	0.9500
C4—H4A	0.9900	C16—H16A	0.9800
C4—H4B	0.9900	C16—H16B	0.9800
C5—C6	1.479 (8)	C16—H16C	0.9800
C5—H5A	0.9900	C17—H17A	0.9800
C5—H5B	0.9900	C17—H17B	0.9800
C6—C7	1.439 (12)	C17—H17C	0.9800
C13—O2—C16	116.4 (3)	O1—C8—H8	116.7
C14—O3—C17	118.1 (3)	C2—C8—H8	116.7
C1—N1—C3	104.9 (3)	N2—C9—C10	113.6 (3)
C1—N2—C2	107.5 (3)	N2—C9—H9A	108.8
C1—N2—C9	126.1 (3)	C10—C9—H9A	108.8
C2—N2—C9	126.3 (3)	N2—C9—H9B	108.8
N1—C1—N2	111.4 (4)	C10—C9—H9B	108.8
N1—C1—C4	126.7 (4)	H9A—C9—H9B	107.7
N2—C1—C4	121.8 (4)	C11—C10—C15	117.3 (3)
C3—C2—N2	103.2 (3)	C11—C10—C9	119.8 (3)
C3—C2—C8	129.7 (4)	C15—C10—C9	123.0 (3)
N2—C2—C8	127.0 (3)	C10—C11—C12	122.7 (3)
N1—C3—C2	112.9 (3)	C10—C11—Br2	121.3 (3)
N1—C3—Cl1	120.9 (3)	C12—C11—Br2	115.8 (3)
C2—C3—Cl1	126.0 (3)	C10—C11—Br1	119.1 (3)
C1—C4—C5	117.1 (5)	C12—C11—Br1	118.2 (3)
C1—C4—H4A	108.0	C13—C12—C11	119.5 (3)
C5—C4—H4A	108.0	C13—C12—H12	120.2
C1—C4—H4B	108.0	C11—C12—H12	120.2
C5—C4—H4B	108.0	C12—C13—O2	125.7 (3)
H4A—C4—H4B	107.3	C12—C13—C14	120.1 (3)
C6—C5—C4	114.9 (6)	O2—C13—C14	114.3 (3)
C6—C5—H5A	108.5	O3—C14—C15	125.9 (3)
C4—C5—H5A	108.5	O3—C14—C13	115.3 (3)
C6—C5—H5B	108.5	C15—C14—C13	118.8 (3)
C4—C5—H5B	108.5	C14—C15—C10	121.7 (3)
H5A—C5—H5B	107.5	C14—C15—H15	119.2
C7—C6—C5	115.7 (8)	C10—C15—H15	119.2
C7—C6—H6A	108.4	O2—C16—H16A	109.5
C5—C6—H6A	108.4	O2—C16—H16B	109.5
C7—C6—H6B	108.4	H16A—C16—H16B	109.5
C5—C6—H6B	108.4	O2—C16—H16C	109.5
H6A—C6—H6B	107.4	H16A—C16—H16C	109.5
C6—C7—H7A	109.5	H16B—C16—H16C	109.5
C6—C7—H7B	109.5	O3—C17—H17A	109.5
H7A—C7—H7B	109.5	O3—C17—H17B	109.5
C6—C7—H7C	109.5	H17A—C17—H17B	109.5
H7A—C7—H7C	109.5	O3—C17—H17C	109.5
H7B—C7—H7C	109.5	H17A—C17—H17C	109.5
O1—C8—C2	126.7 (5)	H17B—C17—H17C	109.5
C3—N1—C1—N2	−0.1 (5)	N2—C9—C10—C15	−15.7 (5)
C3—N1—C1—C4	176.6 (5)	C15—C10—C11—C12	2.4 (5)
C2—N2—C1—N1	0.6 (5)	C9—C10—C11—C12	−177.8 (4)
C9—N2—C1—N1	178.1 (3)	C15—C10—C11—Br2	176.4 (7)
C2—N2—C1—C4	−176.3 (4)	C9—C10—C11—Br2	−3.8 (8)
C9—N2—C1—C4	1.2 (7)	C15—C10—C11—Br1	−174.3 (3)
C1—N2—C2—C3	−0.8 (4)	C9—C10—C11—Br1	5.5 (5)
C9—N2—C2—C3	−178.2 (3)	C10—C11—C12—C13	−1.0 (6)
C1—N2—C2—C8	174.9 (4)	Br2—C11—C12—C13	−175.3 (7)
C9—N2—C2—C8	−2.5 (6)	Br1—C11—C12—C13	175.7 (4)
C1—N1—C3—C2	−0.4 (5)	C11—C12—C13—O2	178.3 (4)
C1—N1—C3—Cl1	−176.3 (3)	C11—C12—C13—C14	−1.2 (6)
N2—C2—C3—N1	0.8 (4)	C16—O2—C13—C12	−4.8 (6)
C8—C2—C3—N1	−174.8 (4)	C16—O2—C13—C14	174.7 (4)
N2—C2—C3—Cl1	176.4 (3)	C17—O3—C14—C15	−3.4 (6)
C8—C2—C3—Cl1	0.8 (7)	C17—O3—C14—C13	177.5 (4)
N1—C1—C4—C5	−15.6 (10)	C12—C13—C14—O3	−178.9 (4)
N2—C1—C4—C5	160.8 (6)	O2—C13—C14—O3	1.5 (5)
C1—C4—C5—C6	−176.9 (7)	C12—C13—C14—C15	1.9 (6)
C4—C5—C6—C7	97.6 (10)	O2—C13—C14—C15	−177.7 (3)
C3—C2—C8—O1	169.7 (5)	O3—C14—C15—C10	−179.5 (3)
N2—C2—C8—O1	−4.9 (8)	C13—C14—C15—C10	−0.4 (5)
C1—N2—C9—C10	105.2 (4)	C11—C10—C15—C14	−1.6 (5)
C2—N2—C9—C10	−77.8 (5)	C9—C10—C15—C14	178.6 (3)
N2—C9—C10—C11	164.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O1	0.99	2.51	2.996 (6)	110
C15—H15···Cg1	0.95	3.00	3.602 (3)	122
C16—H16A···O1^i	0.98	2.59	3.142 (6)	115

Symmetry code: (i) −x, −y, −z.

(II) 2-butyl-4-chloro-1-(6-methyl-1,3-benzodioxol-5-ylmethyl)-1H-imidazole- 5-carboxaldehyde

Crystal data

C17H19ClN2O3	F(000) = 704
Mr = 334.79	Dx = 1.330 Mg m^−3
Monoclinic, P21/n	Melting point: 385 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.4899 (5) Å	Cell parameters from 1237 reflections
b = 9.4887 (3) Å	θ = 5.5–23.6°
c = 14.1018 (5) Å	µ = 0.25 mm^−1
β = 94.319 (1)°	T = 130 K
V = 1666.5 (1) Å^3	Block, colorless
Z = 4	0.11 × 0.10 × 0.08 mm

Data collection

Siemens SMART CCD area-detector diffractometer	2401 independent reflections
Radiation source: fine-focus sealed tube	2090 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
w scans	θmax = 23.3°, θmin = 2.1°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −13→13
Tmin = 0.934, Tmax = 0.982	k = −10→5
6694 measured reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0354P)^2 + 0.5705P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
2401 reflections	Δρmax = 0.18 e Å^−3
211 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0166 (15)

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.

Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d

Plane 1 m1 = −0.54059(0.00123) m2 = 0.79593(0.00041) m3 = −0.27248(0.00265) D = −3.23610(0.00638) Atom d s d/s (d/s)**2 C1 * 0.0322 0.0021 15.651 244.954 C4 * −0.0150 0.0024 − 6.165 38.008 C5 * −0.0683 0.0023 − 29.333 860.435 C6 * 0.0215 0.0030 7.270 52.850 C7 * 0.0549 0.0033 16.648 277.157 N1 0.1098 0.0018 61.659 3801.892 N2 0.0328 0.0016 20.331 413.332 ============ Sum((d/s)**2) for starred atoms 1473.404 Chi-squared at 95% for 2 degrees of freedom: 5.99 The group of atoms deviates significantly from planarity

Plane 2 m1 = −0.53197(0.00048) m2 = 0.77864(0.00033) m3 = −0.33274(0.00024) D = −3.48495(0.00474) Atom d s d/s (d/s)**2 Cl1 * −0.0036 0.0006 − 5.619 31.570 N1 * −0.0004 0.0018 − 0.228 0.052 N2 * 0.0103 0.0016 6.383 40.748 C1 * 0.0027 0.0021 1.320 1.742 C2 * 0.0175 0.0020 8.793 77.316 C3 * 0.0037 0.0021 1.782 3.176 C8 * 0.0436 0.0023 18.790 353.058 C9 * −0.0646 0.0021 − 30.113 906.819 C4 * 0.0289 0.0024 11.928 142.274 O1 0.0848 0.0018 47.741 2279.189 C10 1.2843 0.0019 660.899 436787.625 ============ Sum((d/s)**2) for starred atoms 1556.755 Chi-squared at 95% for 6 degrees of freedom: 12.60 The group of atoms deviates significantly from planarity

Plane 3 m1 = −0.51060(0.00042) m2 = −0.67604(0.00026) m3 = −0.53128(0.00048) D = −8.24660(0.00269) Atom d s d/s (d/s)**2 O2 * −0.0044 0.0018 − 2.422 5.867 O3 * −0.0131 0.0018 − 7.174 51.461 C9 * 0.0363 0.0021 17.180 295.166 C10 * −0.0158 0.0019 − 8.258 68.194 C11 * −0.0099 0.0021 − 4.813 23.166 C12 * −0.0076 0.0023 − 3.301 10.898 C13 * 0.0043 0.0022 1.970 3.881 C14 * −0.0058 0.0021 − 2.741 7.514 C15 * −0.0182 0.0021 − 8.793 77.314 C16 * 0.0074 0.0026 2.805 7.866 C17 * 0.0727 0.0029 25.239 636.991 N2 − 0.1525 0.0016 − 95.360 9093.444 ============ Sum((d/s)**2) for starred atoms 1188.319 Chi-squared at 95% for 8 degrees of freedom: 15.50 The group of atoms deviates significantly from planarity

Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 3.63 (0.15) 176.37 (0.15) 1 3 83.26 (0.10) 96.74 (0.10) 2 3 85.53 (0.03) 94.47 (0.03)

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
Cl1	0.57999 (5)	0.38185 (7)	0.59703 (4)	0.0745 (3)
O1	0.82630 (14)	0.50150 (19)	0.39261 (12)	0.0766 (5)
O2	0.58305 (17)	0.71783 (18)	−0.01039 (12)	0.0800 (5)
O3	0.47714 (15)	0.68771 (19)	0.11624 (13)	0.0814 (5)
N1	0.52146 (14)	0.24137 (19)	0.43849 (12)	0.0552 (5)
N2	0.64549 (13)	0.29981 (17)	0.34053 (11)	0.0474 (4)
C1	0.55578 (16)	0.2244 (2)	0.35181 (14)	0.0496 (5)
C2	0.67150 (16)	0.3713 (2)	0.42515 (14)	0.0482 (5)
C3	0.59277 (17)	0.3303 (2)	0.48201 (14)	0.0509 (5)
C4	0.49993 (19)	0.1356 (3)	0.27625 (16)	0.0626 (6)
H4A	0.5516	0.0665	0.2536	0.075*
H4B	0.4757	0.1965	0.2218	0.075*
C5	0.40416 (18)	0.0573 (2)	0.30956 (16)	0.0604 (6)
H5A	0.4294	−0.0106	0.3596	0.072*
H5B	0.3561	0.1255	0.3383	0.072*
C6	0.3411 (2)	−0.0211 (3)	0.2308 (2)	0.0849 (8)
H6A	0.3881	−0.0933	0.2048	0.102*
H6B	0.3200	0.0459	0.1789	0.102*
C7	0.2414 (3)	−0.0924 (3)	0.2619 (2)	0.1031 (11)
H7A	0.2044	−0.1408	0.2074	0.155*
H7B	0.1935	−0.0216	0.2864	0.155*
H7C	0.2616	−0.1612	0.3119	0.155*
C8	0.75959 (19)	0.4656 (2)	0.44581 (17)	0.0605 (6)
H8	0.7665	0.5042	0.5081	0.073*
C9	0.70788 (17)	0.2990 (2)	0.25658 (14)	0.0538 (5)
H9A	0.6983	0.2067	0.2244	0.065*
H9B	0.7849	0.3090	0.2776	0.065*
C10	0.67716 (15)	0.4144 (2)	0.18554 (13)	0.0449 (5)
C11	0.74152 (17)	0.4317 (2)	0.10945 (14)	0.0514 (5)
C12	0.7141 (2)	0.5334 (2)	0.04015 (15)	0.0611 (6)
H12	0.7574	0.5474	−0.0116	0.073*
C13	0.6244 (2)	0.6119 (2)	0.04838 (14)	0.0569 (6)
C14	0.56169 (17)	0.5946 (2)	0.12356 (15)	0.0540 (5)
C15	0.58636 (17)	0.4971 (2)	0.19294 (14)	0.0511 (5)
H15	0.5427	0.4860	0.2448	0.061*
C16	0.8396 (2)	0.3412 (3)	0.10041 (19)	0.0737 (7)
H16A	0.8766	0.3717	0.0451	0.111*
H16B	0.8178	0.2425	0.0923	0.111*
H16C	0.8882	0.3507	0.1580	0.111*
C17	0.4865 (2)	0.7597 (3)	0.0286 (2)	0.0811 (8)
H17A	0.4242	0.7369	−0.0164	0.097*
H17B	0.4872	0.8628	0.0395	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0843 (5)	0.0918 (5)	0.0485 (4)	−0.0050 (3)	0.0125 (3)	−0.0107 (3)
O1	0.0709 (11)	0.0800 (12)	0.0793 (11)	−0.0178 (9)	0.0085 (9)	0.0166 (9)
O2	0.1118 (15)	0.0665 (11)	0.0610 (10)	0.0006 (10)	0.0024 (10)	0.0165 (8)
O3	0.0869 (12)	0.0754 (12)	0.0820 (12)	0.0272 (10)	0.0086 (9)	0.0176 (10)
N1	0.0558 (11)	0.0634 (11)	0.0479 (10)	−0.0041 (9)	0.0131 (8)	0.0008 (9)
N2	0.0493 (10)	0.0494 (10)	0.0445 (9)	0.0045 (8)	0.0097 (7)	0.0043 (8)
C1	0.0523 (12)	0.0499 (12)	0.0472 (11)	0.0019 (10)	0.0079 (9)	0.0022 (9)
C2	0.0505 (12)	0.0463 (11)	0.0474 (11)	0.0029 (9)	0.0025 (9)	0.0043 (9)
C3	0.0548 (12)	0.0535 (12)	0.0447 (11)	0.0026 (10)	0.0064 (9)	0.0011 (10)
C4	0.0680 (15)	0.0664 (15)	0.0538 (13)	−0.0022 (12)	0.0084 (11)	−0.0055 (11)
C5	0.0617 (14)	0.0581 (13)	0.0606 (13)	−0.0003 (11)	−0.0003 (11)	−0.0026 (11)
C6	0.093 (2)	0.0785 (18)	0.0804 (17)	−0.0088 (16)	−0.0093 (15)	−0.0160 (15)
C7	0.104 (2)	0.088 (2)	0.112 (2)	−0.0362 (19)	−0.0307 (19)	0.0138 (18)
C8	0.0674 (14)	0.0551 (13)	0.0584 (13)	0.0006 (12)	0.0000 (11)	0.0102 (11)
C9	0.0549 (12)	0.0564 (13)	0.0520 (12)	0.0084 (10)	0.0169 (9)	0.0046 (10)
C10	0.0468 (11)	0.0466 (11)	0.0420 (10)	−0.0034 (9)	0.0081 (8)	−0.0046 (9)
C11	0.0542 (12)	0.0514 (12)	0.0500 (11)	−0.0073 (10)	0.0138 (9)	−0.0087 (10)
C12	0.0785 (16)	0.0585 (14)	0.0489 (12)	−0.0126 (13)	0.0229 (11)	−0.0024 (11)
C13	0.0790 (16)	0.0478 (12)	0.0433 (11)	−0.0118 (12)	−0.0002 (10)	0.0004 (10)
C14	0.0598 (13)	0.0484 (12)	0.0532 (12)	0.0018 (11)	0.0009 (10)	−0.0015 (10)
C15	0.0540 (12)	0.0541 (12)	0.0466 (11)	0.0015 (10)	0.0139 (9)	0.0007 (10)
C16	0.0693 (16)	0.0729 (16)	0.0840 (17)	0.0001 (13)	0.0389 (13)	−0.0079 (14)
C17	0.0868 (19)	0.0673 (16)	0.0851 (18)	−0.0060 (15)	−0.0211 (15)	0.0197 (14)

Geometric parameters (Å, º)

Cl1—C3	1.713 (2)	C6—H6B	0.9900
O1—C8	1.211 (3)	C7—H7A	0.9800
O2—C13	1.378 (3)	C7—H7B	0.9800
O2—C17	1.419 (3)	C7—H7C	0.9800
O3—C14	1.375 (3)	C8—H8	0.9500
O3—C17	1.425 (3)	C9—C10	1.514 (3)
N1—C1	1.335 (3)	C9—H9A	0.9900
N1—C3	1.341 (3)	C9—H9B	0.9900
N2—C1	1.349 (3)	C10—C15	1.389 (3)
N2—C2	1.390 (3)	C10—C11	1.398 (3)
N2—C9	1.466 (2)	C11—C12	1.398 (3)
C1—C4	1.490 (3)	C11—C16	1.510 (3)
C2—C3	1.371 (3)	C12—C13	1.357 (3)
C2—C8	1.431 (3)	C12—H12	0.9500
C4—C5	1.513 (3)	C13—C14	1.375 (3)
C4—H4A	0.9900	C14—C15	1.365 (3)
C4—H4B	0.9900	C15—H15	0.9500
C5—C6	1.509 (3)	C16—H16A	0.9800
C5—H5A	0.9900	C16—H16B	0.9800
C5—H5B	0.9900	C16—H16C	0.9800
C6—C7	1.511 (4)	C17—H17A	0.9900
C6—H6A	0.9900	C17—H17B	0.9900
C13—O2—C17	105.22 (18)	O1—C8—C2	127.2 (2)
C14—O3—C17	105.11 (19)	O1—C8—H8	116.4
C1—N1—C3	104.29 (17)	C2—C8—H8	116.4
C1—N2—C2	107.47 (16)	N2—C9—C10	114.03 (16)
C1—N2—C9	126.12 (17)	N2—C9—H9A	108.7
C2—N2—C9	126.29 (17)	C10—C9—H9A	108.7
N1—C1—N2	111.76 (18)	N2—C9—H9B	108.7
N1—C1—C4	123.90 (19)	C10—C9—H9B	108.7
N2—C1—C4	124.33 (18)	H9A—C9—H9B	107.6
C3—C2—N2	103.42 (17)	C15—C10—C11	120.75 (19)
C3—C2—C8	129.2 (2)	C15—C10—C9	121.75 (17)
N2—C2—C8	127.33 (19)	C11—C10—C9	117.45 (18)
N1—C3—C2	113.06 (18)	C12—C11—C10	119.5 (2)
N1—C3—Cl1	120.45 (15)	C12—C11—C16	119.44 (19)
C2—C3—Cl1	126.49 (17)	C10—C11—C16	121.0 (2)
C1—C4—C5	113.21 (18)	C13—C12—C11	118.6 (2)
C1—C4—H4A	108.9	C13—C12—H12	120.7
C5—C4—H4A	108.9	C11—C12—H12	120.7
C1—C4—H4B	108.9	C12—C13—C14	121.5 (2)
C5—C4—H4B	108.9	C12—C13—O2	128.5 (2)
H4A—C4—H4B	107.7	C14—C13—O2	110.0 (2)
C6—C5—C4	113.3 (2)	C15—C14—C13	121.5 (2)
C6—C5—H5A	108.9	C15—C14—O3	128.3 (2)
C4—C5—H5A	108.9	C13—C14—O3	110.15 (19)
C6—C5—H5B	108.9	C14—C15—C10	118.05 (19)
C4—C5—H5B	108.9	C14—C15—H15	121.0
H5A—C5—H5B	107.7	C10—C15—H15	121.0
C5—C6—C7	113.8 (2)	C11—C16—H16A	109.5
C5—C6—H6A	108.8	C11—C16—H16B	109.5
C7—C6—H6A	108.8	H16A—C16—H16B	109.5
C5—C6—H6B	108.8	C11—C16—H16C	109.5
C7—C6—H6B	108.8	H16A—C16—H16C	109.5
H6A—C6—H6B	107.7	H16B—C16—H16C	109.5
C6—C7—H7A	109.5	O2—C17—O3	109.2 (2)
C6—C7—H7B	109.5	O2—C17—H17A	109.8
H7A—C7—H7B	109.5	O3—C17—H17A	109.8
C6—C7—H7C	109.5	O2—C17—H17B	109.8
H7A—C7—H7C	109.5	O3—C17—H17B	109.8
H7B—C7—H7C	109.5	H17A—C17—H17B	108.3
C3—N1—C1—N2	−0.1 (2)	N2—C9—C10—C15	−10.1 (3)
C3—N1—C1—C4	−178.7 (2)	N2—C9—C10—C11	172.30 (18)
C2—N2—C1—N1	−0.2 (2)	C15—C10—C11—C12	0.1 (3)
C9—N2—C1—N1	176.13 (18)	C9—C10—C11—C12	177.67 (19)
C2—N2—C1—C4	178.3 (2)	C15—C10—C11—C16	−179.3 (2)
C9—N2—C1—C4	−5.3 (3)	C9—C10—C11—C16	−1.7 (3)
C1—N2—C2—C3	0.4 (2)	C10—C11—C12—C13	−0.7 (3)
C9—N2—C2—C3	−175.92 (18)	C16—C11—C12—C13	178.7 (2)
C1—N2—C2—C8	−179.2 (2)	C11—C12—C13—C14	1.0 (3)
C9—N2—C2—C8	4.5 (3)	C11—C12—C13—O2	179.3 (2)
C1—N1—C3—C2	0.4 (2)	C17—O2—C13—C12	177.6 (2)
C1—N1—C3—Cl1	−179.79 (15)	C17—O2—C13—C14	−3.9 (2)
N2—C2—C3—N1	−0.5 (2)	C12—C13—C14—C15	−0.5 (3)
C8—C2—C3—N1	179.1 (2)	O2—C13—C14—C15	−179.11 (19)
N2—C2—C3—Cl1	179.67 (15)	C12—C13—C14—O3	178.99 (19)
C8—C2—C3—Cl1	−0.8 (3)	O2—C13—C14—O3	0.4 (3)
N1—C1—C4—C5	−4.2 (3)	C17—O3—C14—C15	−177.3 (2)
N2—C1—C4—C5	177.37 (19)	C17—O3—C14—C13	3.3 (3)
C1—C4—C5—C6	174.3 (2)	C13—C14—C15—C10	−0.2 (3)
C4—C5—C6—C7	−176.4 (2)	O3—C14—C15—C10	−179.6 (2)
C3—C2—C8—O1	−178.2 (2)	C11—C10—C15—C14	0.4 (3)
N2—C2—C8—O1	1.2 (4)	C9—C10—C15—C14	−177.10 (19)
C1—N2—C9—C10	93.9 (2)	C13—O2—C17—O3	6.0 (3)
C2—N2—C9—C10	−90.4 (2)	C14—O3—C17—O2	−5.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O1	0.99	2.47	3.022 (3)	115
C9—H9A···O1^i	0.99	2.57	3.528 (3)	167
C15—H15···Cg1	0.95	2.97	3.585 (2)	124
C17—H17A···Cg2^ii	0.99	2.89	3.654 (3)	135

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