Three tetrahydroisoquinolinedione derivatives

N-(2-Chloro­benzyl)-1,2,3,4-tetra­hydro­iso­quinoline-1,3-dione, C₁₆H₁₂ClNO₂, crystallizes in P2₁/n with three crystallographically independent mol­ecules in the asymmetric unit, which differ slightly in conformation, N-(2-bromo-4-methyl­phenyl)-1,2,3,4-tetra­hydro­iso­quinoline-1,3-dione, C₁₆H₁₂BrNO₂, crystallizes in P2₁/n with one mol­ecule in the asymmetric unit andN-(2,3-di­chloro­phenyl)-1,2,3,4-tetra­hydro­iso­quinoline-1,3-dione, C₁₅H₉Cl₂NO₂, crystallizes in P2₁/c with one mol­ecule in the asymmetric unit. In all three structures, the heterocyclic rings adopt approximately planar conformations. The pyridine rings are orthogonal to the substituted phenyl rings. In all three structures, the crystal packing is stabilized by intermolecular C—H...O hydrogen bonds.

S1. Comment

Isoquinoline is a well known ligand that has been used in studies of the formation of various adducts of group IVA halides (Miller & Onyszchuk, 1967). Tetrahydroisoquinolines represent a class of biologically active phenyl ethylamines (Brzezinska, 1994), and these compounds are of great interest due to their biological and pharmacological properties. They are also useful as key intermediates in the synthesis of isoquinoline alkaloids, such as cherylline and latifine (Honda et al., 2001). Isoquinoline fused-ring systems such as pyrroloisoquinoline show valuable pharmacological activity, e.g. antileukemic (Anderson et al., 1998), muscaricinic, agonostic (Loesel et al., 1987) and antidepressant properties (Elwan et al., 1996). Their marked antidepressant, tranquilizing (Sulkowski & Willie, 1969), analgesic and sedative (Hamamato & Kajiwara, 1966) activity renders 1(2H)-isoquinolines an important class of compounds. These compounds have also been used as intermediates for the synthesis of a number of naturally occurring alkaloids (Kobayashi, 1950; Walker et al., 1964). A variety of 1,2,3,4-tetrahydroisoquinoline derivatives have been studied extensively in the past in order to elucidate their antidepressant-like activity. The title compounds, N-(2-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione, (I), N-(2-bromo-4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione, (II), and N-(2,3-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione, (III), are of interest as intermediates in the synthesis of alkaloids such as corgoine (Kametani et al., 1975) and sendaverine (Kametani et al., 1979). \sch

The structures in the present study consist of an isoquinoline moiety and a substituted phenyl ring. Structure (I) contains three molecules in the asymmetric unit, designated (IA), (IB) and (IC) (Fig. 1). Structures (II) (Fig. 2) and (III) (Fig. 3) contain one molecule per asymmetric unit.

The C═O bond lengths in all three structures, and Csp²—Br in (II) and Csp²—Cl in (III), are comparable with the values found in a search of the Cambridge Structural Database (Release?; Allen et al., 1987). The bond distances and angles of the isoquinoline moiety in these structures are in good agreement with the values reported for other 1,2,3,4-tetrahydroisoquinoline derivatives (Bellard et al., 1982; Plywaczyk et al., 1984). Selected geometric parameters for (I), (II) and (III) are given in Tables 1, 3 and 5, respectively.

In (I), the phenyl rings of the benzyl groups are twisted with respect to the isoquinoline system. The torsion angles around the N1—C16 and C16—C10 single bonds are almost equal for (IB) and (IC) but are different for (IA). This shows that the orientation of the benzyl group in (IA) is different from that in (IB) and (IC).

The isoquinoline moiety is slightly folded about the line passing through atoms C8 and C9, and the dihedral angle between the two halves ranges from 2.2 (1) to 3.7 (1)°. The phenyl ring in all three structures is orthogonal to the isoquinoline moiety, forming a dihedral angle of 87.6 (1)° in (IA), 85.7 (1)° in (IB), 84.5 (1)° in (IC), 76.6 (1)° in (II) and 69.9 (1)° in (III). It can be seen that the value in (III) is lower than that in (II), and this is probably a result of the heavier substituents in the phenyl ring of (II). Query.

The dihedral angle between the least-squares planes of the substituted phenyl and benzo-fused rings is 88.2 (1)° for (IA), 85.2 (1)° for (IB), 84.4 (1)° for (IC), 75.6 (0)° for (II) and 69.3 (1)° for (III). The deviations of atoms O1 and O2 from the mean planes defined by atoms N1, C1, C2, C9, C8 and C7 are -0.098 (2) and 0.040 (1) Å, respectively, in (IA), -0.084 (3) and 0.071 (3) Å, respectively, in (IB), -0.108 (3) and 0.086 (3) Å, respectively, in (IC), -0.072 (0) and 0.016 (0) Å, respectively, in (II), and -0.237 (2) and 0.149 (2) Å, respectively, in (III).

In all three structures, the bond lengths and angles, the dihedral angles between the two halves of the isoquinoline moiety, and the dihedral angles between the isoquinoline moiety and the phenyl ring are comparable with those observed in similar structures (Ammon & Wheeler, 1974).

In addition to normal van der Waals interactions, the crystal packing in all three structures is stabilized by intermolecular C—H···O hydrogen bonds. In (I), five intermolecular C—H···O hydrogen bonds occur, with H···O distances less than the sum of the van der Waals radii (Bondi, 1964). In this structure, the symmetry-related isoquinoline molecules are arranged in a head-to-head manner and are alternately parallel to each other. This type of stacking is also found in 1,4-dihydroisoquinoline (Minter et al., 1996). In (II), an intermolecular C—H···O hydrogen bond between atoms C5 and O1 stabilizes the crystal packing. The interesting feature of the crystal structure of (III) is that a single C—H···O hydrogen bond links the molecules into cyclic centrosymmetric dimers formed by an R₂²(16) ring system. This is a layered structure, with layers parallel to the ac plane. Details of the hydrogen-bond geometry in (I), (II) and (III) are given in Tables 2, 4 and 6, respectively.

The most remarkable feature of the crystal structure of (II) is the existence of short intermolecular halogen···O contact, Br1···O2ⁱ 3.012 (3) Å [symmetry code: (i) 1/2 - x, y + 1/2, 3/2 - z], between the phenyl ring and the isoquinoline moiety.

S2. Experimental

The title compounds were synthesized from homophthalic acid and the corresponding substituted aromatic amines. The yields were 75% (m.p. 435–437 K) for (I), 71% (m.p. 395–397 K) for (II) and 68% (m.p. 471–473 K) for (III). The compounds were dissolved in a mixture of ethyl acetate and hexane (4:1). Slow evaporation of the solvent at room temperature produced crystals from which the experimental samples were obtained.

S3. Refinement

For all three compounds, all H atoms were geometrically fixed and allowed to ride on their parent atoms, with C—H = 0.93–0.99 Å, and U_iso = 1.5U_eq(C) for methyl H atoms and 1.2 U_eq(C) for other H atoms.

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989) for (I); CAD-4 EXPRESS (Enraf Nonius, 1994) for (II), (III). Cell refinement: CAD-4 Software for (I); CAD-4 EXPRESS for (II), (III). Data reduction: TEXSAN (Molecular Structure Corporation, 1985) for (I); XCAD4 (Harms & Wocadlo, 1995) for (II), (III). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures

	Fig. 1. A view of the three independent molecules of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the molecular structure of (II) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 3. A view of the molecular structure of (III) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

(I) N-(2-Chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione

Crystal data

C16H12ClNO2	F(000) = 1776
Mr = 285.72	Dx = 1.410 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 7.7922 (14) Å	Cell parameters from 25 reflections
b = 21.538 (4) Å	θ = 20–30°
c = 24.351 (5) Å	µ = 2.52 mm^−1
β = 98.92 (2)°	T = 293 K
V = 4037.4 (13) Å^3	Prism, colourless
Z = 12	0.50 × 0.41 × 0.20 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	5013 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Graphite monochromator	θmax = 68.2°, θmin = 5.5°
ω/2θ scans	h = 0→9
Absorption correction: empirical (using intensity measurements) via ψ scans (North et al., 1968)	k = 0→25
Tmin = 0.366, Tmax = 0.633	l = −29→28
7916 measured reflections	3 standard reflections every 200 reflections
7348 independent reflections	intensity decay: 0.6%

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)] = 0.065	H-atom parameters constrained
wR(F^2) = 0.200	w = 1/[σ^2(Fo^2) + (0.1067P)^2 + 1.2945P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
7348 reflections	Δρmax = 0.38 e Å^−3
542 parameters	Δρmin = −0.34 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0016 (2)

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
Cl1A	0.97253 (16)	0.75637 (5)	0.33096 (6)	0.1079 (4)
N1A	0.8330 (4)	0.59516 (13)	0.42749 (11)	0.0625 (7)
O1A	0.8642 (4)	0.55336 (13)	0.34525 (10)	0.0839 (8)
O2A	0.8095 (5)	0.63704 (13)	0.51103 (12)	0.0998 (10)
C1A	0.8301 (5)	0.54512 (17)	0.39165 (13)	0.0629 (8)
C2A	0.7782 (5)	0.48367 (16)	0.41021 (13)	0.0692 (9)
H2A1	0.8652	0.4529	0.4019	0.083*
H2A2	0.6660	0.4724	0.3875	0.083*
C3A	0.7317 (5)	0.41894 (17)	0.49172 (15)	0.0719 (10)
H3A	0.7259	0.3832	0.4686	0.086*
C4A	0.7129 (5)	0.4130 (2)	0.54606 (17)	0.0801 (11)
H4A	0.6976	0.3729	0.5609	0.096*
C5A	0.7159 (5)	0.4639 (2)	0.57951 (16)	0.0830 (12)
H5A	0.6998	0.4592	0.6172	0.100*
C6A	0.7422 (5)	0.52244 (19)	0.55884 (14)	0.0751 (10)
H6A	0.7440	0.5580	0.5821	0.090*
C7A	0.8029 (5)	0.59081 (17)	0.48238 (14)	0.0674 (9)
C8A	0.7660 (4)	0.52861 (16)	0.50335 (13)	0.0591 (8)
C9A	0.7593 (4)	0.47705 (15)	0.46972 (13)	0.0566 (8)
C10A	0.7293 (4)	0.68657 (14)	0.37006 (13)	0.0581 (8)
C11A	0.7593 (5)	0.73405 (15)	0.33435 (16)	0.0702 (9)
C12A	0.6248 (7)	0.7641 (2)	0.3020 (2)	0.0944 (13)
H12A	0.6486	0.7963	0.2776	0.113*
C13A	0.4570 (6)	0.7477 (2)	0.30459 (19)	0.0897 (13)
H13A	0.3639	0.7693	0.2828	0.108*
C14A	0.4235 (5)	0.7006 (2)	0.33840 (17)	0.0807 (11)
H14A	0.3073	0.6884	0.3400	0.097*
C15A	0.5596 (5)	0.67084 (18)	0.37016 (16)	0.0744 (10)
H15A	0.5346	0.6377	0.3934	0.089*
C16A	0.8788 (5)	0.65554 (17)	0.40652 (16)	0.0726 (10)
H16E	0.9757	0.6500	0.3850	0.087*
H16F	0.9201	0.6830	0.4384	0.087*
Cl1B	0.25039 (13)	0.27435 (5)	0.02324 (5)	0.0827 (3)
N1B	0.1484 (3)	0.44858 (13)	0.10985 (11)	0.0602 (7)
O1B	0.2034 (4)	0.47403 (14)	0.02456 (11)	0.0890 (8)
O2B	0.0940 (4)	0.42243 (12)	0.19529 (11)	0.0809 (7)
C1B	0.1646 (4)	0.49158 (18)	0.06820 (14)	0.0639 (9)
C2B	0.1299 (5)	0.55794 (17)	0.07851 (13)	0.0671 (9)
H2B1	0.2295	0.5825	0.0698	0.081*
H2B2	0.0265	0.5707	0.0520	0.081*
C3B	0.0834 (5)	0.63678 (17)	0.14993 (15)	0.0728 (10)
H3B	0.0943	0.6687	0.1237	0.087*
C4B	0.0513 (6)	0.65202 (19)	0.20233 (17)	0.0839 (12)
H4B	0.0379	0.6944	0.2118	0.101*
C5B	0.0384 (5)	0.60659 (19)	0.24109 (16)	0.0790 (11)
H5B	0.0168	0.6176	0.2772	0.095*
C6B	0.0566 (5)	0.54569 (17)	0.22764 (14)	0.0663 (9)
H6B	0.0477	0.5142	0.2544	0.080*
C7B	0.1087 (4)	0.46346 (16)	0.16191 (13)	0.0598 (8)
C8B	0.0882 (4)	0.52974 (15)	0.17476 (12)	0.0540 (7)
C9B	0.0999 (4)	0.57507 (16)	0.13517 (13)	0.0576 (8)
C10B	0.0256 (4)	0.35185 (15)	0.06401 (13)	0.0559 (7)
C11B	0.0441 (4)	0.30199 (15)	0.02938 (13)	0.0580 (8)
C12B	−0.0975 (5)	0.27190 (17)	0.00031 (16)	0.0738 (10)
H12B	−0.0813	0.2380	−0.0234	0.089*
C13B	−0.2625 (5)	0.29106 (19)	0.00565 (17)	0.0778 (11)
H13B	−0.3605	0.2702	−0.0141	0.093*
C14B	−0.2853 (5)	0.34018 (19)	0.03954 (18)	0.0786 (11)
H14B	−0.3990	0.3538	0.0431	0.094*
C15B	−0.1422 (5)	0.36954 (18)	0.06827 (16)	0.0719 (9)
H15B	−0.1594	0.4033	0.0920	0.086*
C16B	0.1798 (4)	0.38311 (16)	0.09724 (16)	0.0701 (9)
H16A	0.2127	0.3603	0.1326	0.084*
H16B	0.2789	0.3808	0.0763	0.084*
Cl1C	1.07537 (16)	−0.18148 (5)	0.15379 (6)	0.1052 (4)
N1C	0.9770 (3)	−0.03383 (12)	0.27012 (10)	0.0572 (6)
O1C	1.0418 (4)	0.00997 (13)	0.19228 (10)	0.0839 (8)
O2C	0.9143 (4)	−0.07817 (12)	0.34833 (10)	0.0825 (8)
C1C	0.9998 (4)	0.01755 (17)	0.23739 (13)	0.0624 (8)
C2C	0.9661 (5)	0.08015 (16)	0.25877 (14)	0.0680 (9)
H1C1	0.8635	0.0977	0.2347	0.082*
H1C2	1.0665	0.1070	0.2547	0.082*
C3C	0.9223 (5)	0.14154 (18)	0.34284 (16)	0.0773 (11)
H3C	0.9349	0.1786	0.3226	0.093*
C4C	0.8918 (6)	0.1452 (2)	0.39634 (18)	0.0890 (12)
H4C	0.8830	0.1848	0.4129	0.107*
C5C	0.8737 (5)	0.0925 (2)	0.42657 (15)	0.0810 (11)
H5C	0.8526	0.0956	0.4639	0.097*
C6C	0.8861 (5)	0.03540 (18)	0.40264 (14)	0.0669 (9)
H6C	0.8724	−0.0013	0.4232	0.080*
C7C	0.9346 (4)	−0.03072 (15)	0.32361 (13)	0.0578 (8)
C8C	0.9190 (4)	0.03115 (15)	0.34812 (12)	0.0540 (7)
C9C	0.9351 (4)	0.08437 (15)	0.31746 (13)	0.0584 (8)
C10C	0.8500 (4)	−0.11897 (14)	0.20870 (13)	0.0575 (8)
C11C	0.8677 (5)	−0.16024 (15)	0.16607 (15)	0.0659 (9)
C12C	0.7265 (6)	−0.18443 (18)	0.13214 (17)	0.0829 (12)
H12C	0.7427	−0.2124	0.1032	0.099*
C13C	0.5625 (6)	−0.16814 (19)	0.14008 (18)	0.0858 (12)
H13C	0.4643	−0.1847	0.1167	0.103*
C14C	0.5406 (5)	−0.12768 (18)	0.18197 (16)	0.0746 (10)
H14C	0.4271	−0.1161	0.1877	0.090*
C15C	0.6828 (4)	−0.10409 (16)	0.21552 (14)	0.0641 (8)
H15C	0.6655	−0.0764	0.2446	0.077*
C16C	1.0054 (4)	−0.09482 (16)	0.24707 (15)	0.0655 (9)
H16C	1.0361	−0.1246	0.2780	0.079*
H16D	1.1052	−0.0923	0.2265	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.0979 (8)	0.0789 (7)	0.1469 (11)	−0.0175 (6)	0.0185 (7)	0.0375 (7)
N1A	0.0757 (18)	0.0572 (16)	0.0525 (15)	0.0018 (13)	0.0036 (13)	0.0112 (12)
O1A	0.108 (2)	0.0937 (19)	0.0539 (14)	0.0040 (16)	0.0262 (14)	0.0138 (13)
O2A	0.161 (3)	0.0641 (17)	0.0722 (17)	0.0108 (18)	0.0105 (18)	−0.0127 (14)
C1A	0.073 (2)	0.068 (2)	0.0473 (18)	0.0074 (17)	0.0094 (15)	0.0063 (15)
C2A	0.099 (3)	0.061 (2)	0.0491 (18)	0.0054 (19)	0.0160 (17)	0.0027 (15)
C3A	0.086 (3)	0.064 (2)	0.069 (2)	0.0114 (18)	0.0221 (19)	0.0131 (17)
C4A	0.087 (3)	0.078 (3)	0.081 (3)	0.019 (2)	0.032 (2)	0.026 (2)
C5A	0.092 (3)	0.101 (3)	0.063 (2)	0.024 (2)	0.032 (2)	0.029 (2)
C6A	0.092 (3)	0.085 (3)	0.0511 (18)	0.027 (2)	0.0208 (18)	0.0035 (18)
C7A	0.083 (2)	0.066 (2)	0.0500 (18)	0.0165 (18)	0.0027 (16)	0.0028 (16)
C8A	0.067 (2)	0.065 (2)	0.0445 (16)	0.0163 (16)	0.0081 (14)	0.0082 (14)
C9A	0.0616 (19)	0.0594 (19)	0.0493 (16)	0.0105 (15)	0.0104 (14)	0.0052 (14)
C10A	0.072 (2)	0.0479 (17)	0.0524 (17)	−0.0006 (15)	0.0042 (15)	−0.0012 (14)
C11A	0.088 (3)	0.0495 (18)	0.072 (2)	−0.0023 (17)	0.0096 (19)	0.0037 (16)
C12A	0.108 (4)	0.071 (3)	0.101 (3)	0.012 (2)	0.004 (3)	0.031 (2)
C13A	0.094 (3)	0.079 (3)	0.089 (3)	0.025 (2)	−0.005 (2)	0.012 (2)
C14A	0.073 (2)	0.084 (3)	0.084 (3)	0.011 (2)	0.009 (2)	0.000 (2)
C15A	0.076 (2)	0.076 (2)	0.072 (2)	0.0010 (19)	0.0128 (18)	0.0151 (19)
C16A	0.078 (2)	0.067 (2)	0.070 (2)	−0.0086 (18)	0.0028 (18)	0.0144 (18)
Cl1B	0.0840 (7)	0.0703 (6)	0.0966 (7)	0.0080 (5)	0.0232 (5)	−0.0137 (5)
N1B	0.0621 (16)	0.0587 (16)	0.0578 (16)	−0.0032 (13)	0.0031 (12)	−0.0114 (13)
O1B	0.104 (2)	0.103 (2)	0.0648 (16)	−0.0080 (16)	0.0279 (14)	−0.0244 (15)
O2B	0.110 (2)	0.0646 (15)	0.0678 (15)	−0.0086 (14)	0.0141 (14)	0.0081 (13)
C1B	0.061 (2)	0.078 (2)	0.0524 (19)	−0.0087 (17)	0.0079 (15)	−0.0103 (17)
C2B	0.084 (2)	0.070 (2)	0.0475 (17)	−0.0038 (18)	0.0123 (16)	0.0009 (16)
C3B	0.099 (3)	0.058 (2)	0.062 (2)	0.0001 (19)	0.0149 (19)	0.0055 (17)
C4B	0.114 (3)	0.066 (2)	0.075 (3)	−0.001 (2)	0.025 (2)	−0.016 (2)
C5B	0.102 (3)	0.079 (3)	0.059 (2)	−0.007 (2)	0.023 (2)	−0.0142 (19)
C6B	0.079 (2)	0.070 (2)	0.0513 (18)	−0.0149 (18)	0.0138 (16)	−0.0025 (16)
C7B	0.067 (2)	0.062 (2)	0.0493 (17)	−0.0091 (16)	0.0051 (15)	−0.0046 (15)
C8B	0.0580 (18)	0.0578 (18)	0.0457 (16)	−0.0066 (14)	0.0068 (13)	−0.0028 (14)
C9B	0.0631 (19)	0.0610 (19)	0.0488 (17)	−0.0034 (15)	0.0088 (14)	−0.0030 (14)
C10B	0.0605 (19)	0.0552 (18)	0.0511 (17)	−0.0029 (15)	0.0059 (14)	−0.0017 (14)
C11B	0.070 (2)	0.0508 (17)	0.0526 (17)	−0.0003 (15)	0.0084 (15)	0.0024 (14)
C12B	0.096 (3)	0.057 (2)	0.066 (2)	−0.0093 (19)	0.006 (2)	−0.0084 (17)
C13B	0.073 (3)	0.071 (2)	0.083 (3)	−0.019 (2)	−0.006 (2)	0.001 (2)
C14B	0.062 (2)	0.082 (3)	0.090 (3)	−0.0044 (19)	0.008 (2)	0.002 (2)
C15B	0.067 (2)	0.073 (2)	0.075 (2)	−0.0013 (18)	0.0100 (18)	−0.0103 (19)
C16B	0.061 (2)	0.065 (2)	0.080 (2)	0.0029 (16)	−0.0016 (17)	−0.0159 (18)
Cl1C	0.1139 (9)	0.0807 (7)	0.1317 (10)	−0.0057 (6)	0.0528 (8)	−0.0374 (7)
N1C	0.0655 (16)	0.0561 (15)	0.0507 (14)	−0.0059 (13)	0.0108 (12)	−0.0022 (12)
O1C	0.109 (2)	0.0955 (19)	0.0525 (14)	−0.0224 (16)	0.0301 (13)	−0.0078 (13)
O2C	0.120 (2)	0.0611 (15)	0.0701 (16)	−0.0101 (14)	0.0269 (15)	0.0117 (12)
C1C	0.067 (2)	0.071 (2)	0.0495 (18)	−0.0143 (17)	0.0121 (15)	0.0002 (15)
C2C	0.091 (3)	0.061 (2)	0.0517 (18)	−0.0075 (18)	0.0119 (17)	0.0081 (15)
C3C	0.107 (3)	0.058 (2)	0.065 (2)	0.005 (2)	0.007 (2)	−0.0013 (17)
C4C	0.120 (4)	0.072 (3)	0.074 (3)	0.009 (2)	0.016 (2)	−0.018 (2)
C5C	0.094 (3)	0.096 (3)	0.055 (2)	0.000 (2)	0.0166 (19)	−0.014 (2)
C6C	0.078 (2)	0.074 (2)	0.0499 (18)	−0.0070 (18)	0.0130 (16)	0.0017 (16)
C7C	0.065 (2)	0.0581 (19)	0.0501 (17)	−0.0094 (15)	0.0092 (14)	0.0034 (14)
C8C	0.0548 (17)	0.0606 (19)	0.0455 (16)	−0.0062 (14)	0.0044 (13)	0.0019 (14)
C9C	0.068 (2)	0.0554 (18)	0.0488 (17)	−0.0044 (15)	0.0012 (14)	0.0001 (14)
C10C	0.070 (2)	0.0484 (17)	0.0541 (18)	−0.0059 (15)	0.0105 (15)	0.0053 (13)
C11C	0.082 (2)	0.0483 (17)	0.071 (2)	−0.0070 (16)	0.0228 (18)	−0.0027 (16)
C12C	0.114 (4)	0.061 (2)	0.075 (2)	−0.026 (2)	0.019 (2)	−0.0125 (19)
C13C	0.097 (3)	0.077 (3)	0.077 (3)	−0.033 (2)	−0.005 (2)	0.002 (2)
C14C	0.071 (2)	0.075 (2)	0.075 (2)	−0.0121 (19)	0.0040 (19)	0.008 (2)
C15C	0.070 (2)	0.064 (2)	0.0582 (19)	−0.0052 (17)	0.0086 (16)	0.0017 (16)
C16C	0.067 (2)	0.0602 (19)	0.070 (2)	0.0023 (16)	0.0106 (17)	−0.0067 (16)

Geometric parameters (Å, º)

Cl1A—C11A	1.743 (4)	C6B—C8B	1.391 (4)
N1A—C1A	1.385 (4)	C6B—H6B	0.9500
N1A—C7A	1.396 (4)	C7B—C8B	1.476 (5)
N1A—C16A	1.462 (4)	C8B—C9B	1.385 (4)
O1A—C1A	1.213 (4)	C10B—C15B	1.381 (5)
O2A—C7A	1.212 (4)	C10B—C11B	1.387 (4)
C1A—C2A	1.475 (5)	C10B—C16B	1.500 (4)
C2A—C9A	1.486 (4)	C11B—C12B	1.377 (5)
C2A—H2A1	0.9900	C12B—C13B	1.375 (5)
C2A—H2A2	0.9900	C12B—H12B	0.9500
C3A—C4A	1.360 (5)	C13B—C14B	1.370 (6)
C3A—C9A	1.391 (5)	C13B—H13B	0.9500
C3A—H3A	0.9500	C14B—C15B	1.375 (5)
C4A—C5A	1.364 (6)	C14B—H14B	0.9500
C4A—H4A	0.9500	C15B—H15B	0.9500
C5A—C6A	1.385 (6)	C16B—H16A	0.9900
C5A—H5A	0.9500	C16B—H16B	0.9900
C6A—C8A	1.399 (4)	Cl1C—C11C	1.751 (4)
C6A—H6A	0.9500	N1C—C1C	1.391 (4)
C7A—C8A	1.478 (5)	N1C—C7C	1.394 (4)
C8A—C9A	1.376 (5)	N1C—C16C	1.459 (4)
C10A—C15A	1.365 (5)	O1C—C1C	1.205 (4)
C10A—C11A	1.386 (5)	O2C—C7C	1.209 (4)
C10A—C16A	1.507 (5)	C1C—C2C	1.483 (5)
C11A—C12A	1.372 (5)	C2C—C9C	1.489 (4)
C12A—C13A	1.366 (6)	C2C—H1C1	0.9900
C12A—H12A	0.9500	C2C—H1C2	0.9900
C13A—C14A	1.357 (6)	C3C—C4C	1.362 (5)
C13A—H13A	0.9500	C3C—C9C	1.388 (5)
C14A—C15A	1.371 (5)	C3C—H3C	0.9500
C14A—H14A	0.9500	C4C—C5C	1.372 (6)
C15A—H15A	0.9500	C4C—H4C	0.9500
C16A—H16E	0.9900	C5C—C6C	1.371 (5)
C16A—H16F	0.9900	C5C—H5C	0.9500
Cl1B—C11B	1.742 (3)	C6C—C8C	1.393 (4)
N1B—C7B	1.388 (4)	C6C—H6C	0.9500
N1B—C1B	1.394 (4)	C7C—C8C	1.473 (5)
N1B—C16B	1.472 (4)	C8C—C9C	1.384 (4)
O1B—C1B	1.210 (4)	C10C—C15C	1.377 (5)
O2B—C7B	1.218 (4)	C10C—C11C	1.389 (5)
C1B—C2B	1.483 (5)	C10C—C16C	1.503 (5)
C2B—C9B	1.481 (4)	C11C—C12C	1.372 (5)
C2B—H2B1	0.9900	C12C—C13C	1.368 (6)
C2B—H2B2	0.9900	C12C—H12C	0.9500
C3B—C4B	1.378 (5)	C13C—C14C	1.372 (6)
C3B—C9B	1.388 (5)	C13C—H13C	0.9500
C3B—H3B	0.9500	C14C—C15C	1.368 (5)
C4B—C5B	1.374 (6)	C14C—H14C	0.9500
C4B—H4B	0.9500	C15C—H15C	0.9500
C5B—C6B	1.365 (5)	C16C—H16C	0.9900
C5B—H5B	0.9500	C16C—H16D	0.9900
C1A—N1A—C7A	124.2 (3)	C6B—C8B—C7B	118.4 (3)
C1A—N1A—C16A	117.0 (3)	C8B—C9B—C3B	118.4 (3)
C7A—N1A—C16A	118.7 (3)	C8B—C9B—C2B	120.6 (3)
O1A—C1A—N1A	119.2 (3)	C3B—C9B—C2B	120.9 (3)
O1A—C1A—C2A	121.8 (3)	C15B—C10B—C11B	116.7 (3)
N1A—C1A—C2A	118.9 (3)	C15B—C10B—C16B	121.6 (3)
C1A—C2A—C9A	117.3 (3)	C11B—C10B—C16B	121.7 (3)
C1A—C2A—H2A1	108.0	C12B—C11B—C10B	121.7 (3)
C9A—C2A—H2A1	108.0	C12B—C11B—Cl1B	118.1 (3)
C1A—C2A—H2A2	108.0	C10B—C11B—Cl1B	120.1 (3)
C9A—C2A—H2A2	108.0	C13B—C12B—C11B	119.8 (4)
H2A1—C2A—H2A2	107.2	C13B—C12B—H12B	120.1
C4A—C3A—C9A	120.4 (4)	C11B—C12B—H12B	120.1
C4A—C3A—H3A	119.8	C14B—C13B—C12B	119.9 (4)
C9A—C3A—H3A	119.8	C14B—C13B—H13B	120.0
C3A—C4A—C5A	120.7 (4)	C12B—C13B—H13B	120.0
C3A—C4A—H4A	119.6	C13B—C14B—C15B	119.4 (4)
C5A—C4A—H4A	119.6	C13B—C14B—H14B	120.3
C4A—C5A—C6A	120.3 (3)	C15B—C14B—H14B	120.3
C4A—C5A—H5A	119.8	C14B—C15B—C10B	122.5 (4)
C6A—C5A—H5A	119.8	C14B—C15B—H15B	118.8
C5A—C6A—C8A	119.1 (4)	C10B—C15B—H15B	118.8
C5A—C6A—H6A	120.4	N1B—C16B—C10B	113.4 (3)
C8A—C6A—H6A	120.4	N1B—C16B—H16A	108.9
O2A—C7A—N1A	119.8 (3)	C10B—C16B—H16A	108.9
O2A—C7A—C8A	122.6 (3)	N1B—C16B—H16B	108.9
N1A—C7A—C8A	117.5 (3)	C10B—C16B—H16B	108.9
C9A—C8A—C6A	120.0 (3)	H16A—C16B—H16B	107.7
C9A—C8A—C7A	121.2 (3)	C1C—N1C—C7C	124.5 (3)
C6A—C8A—C7A	118.8 (3)	C1C—N1C—C16C	117.1 (3)
C8A—C9A—C3A	119.4 (3)	C7C—N1C—C16C	118.4 (3)
C8A—C9A—C2A	120.2 (3)	O1C—C1C—N1C	119.4 (3)
C3A—C9A—C2A	120.4 (3)	O1C—C1C—C2C	122.1 (3)
C15A—C10A—C11A	116.2 (3)	N1C—C1C—C2C	118.5 (3)
C15A—C10A—C16A	123.3 (3)	C1C—C2C—C9C	117.2 (3)
C11A—C10A—C16A	120.4 (3)	C1C—C2C—H1C1	108.0
C12A—C11A—C10A	121.3 (4)	C9C—C2C—H1C1	108.0
C12A—C11A—Cl1A	119.4 (3)	C1C—C2C—H1C2	108.0
C10A—C11A—Cl1A	119.2 (3)	C9C—C2C—H1C2	108.0
C13A—C12A—C11A	120.2 (4)	H1C1—C2C—H1C2	107.3
C13A—C12A—H12A	119.9	C4C—C3C—C9C	120.8 (4)
C11A—C12A—H12A	119.9	C4C—C3C—H3C	119.6
C14A—C13A—C12A	119.8 (4)	C9C—C3C—H3C	119.6
C14A—C13A—H13A	120.1	C3C—C4C—C5C	120.8 (4)
C12A—C13A—H13A	120.1	C3C—C4C—H4C	119.6
C13A—C14A—C15A	119.2 (4)	C5C—C4C—H4C	119.6
C13A—C14A—H14A	120.4	C6C—C5C—C4C	119.6 (3)
C15A—C14A—H14A	120.4	C6C—C5C—H5C	120.2
C10A—C15A—C14A	123.2 (4)	C4C—C5C—H5C	120.2
C10A—C15A—H15A	118.4	C5C—C6C—C8C	120.0 (3)
C14A—C15A—H15A	118.4	C5C—C6C—H6C	120.0
N1A—C16A—C10A	113.1 (3)	C8C—C6C—H6C	120.0
N1A—C16A—H16E	109.0	O2C—C7C—N1C	119.5 (3)
C10A—C16A—H16E	109.0	O2C—C7C—C8C	122.5 (3)
N1A—C16A—H16F	109.0	N1C—C7C—C8C	117.9 (3)
C10A—C16A—H16F	109.0	C9C—C8C—C6C	120.3 (3)
H16E—C16A—H16F	107.8	C9C—C8C—C7C	120.7 (3)
C7B—N1B—C1B	124.7 (3)	C6C—C8C—C7C	119.0 (3)
C7B—N1B—C16B	118.7 (3)	C8C—C9C—C3C	118.4 (3)
C1B—N1B—C16B	116.6 (3)	C8C—C9C—C2C	120.6 (3)
O1B—C1B—N1B	119.7 (3)	C3C—C9C—C2C	121.0 (3)
O1B—C1B—C2B	121.8 (3)	C15C—C10C—C11C	116.4 (3)
N1B—C1B—C2B	118.5 (3)	C15C—C10C—C16C	122.1 (3)
C9B—C2B—C1B	117.2 (3)	C11C—C10C—C16C	121.5 (3)
C9B—C2B—H2B1	108.0	C12C—C11C—C10C	122.0 (4)
C1B—C2B—H2B1	108.0	C12C—C11C—Cl1C	118.3 (3)
C9B—C2B—H2B2	108.0	C10C—C11C—Cl1C	119.7 (3)
C1B—C2B—H2B2	108.0	C13C—C12C—C11C	119.8 (4)
H2B1—C2B—H2B2	107.2	C13C—C12C—H12C	120.1
C4B—C3B—C9B	120.4 (3)	C11C—C12C—H12C	120.1
C4B—C3B—H3B	119.8	C12C—C13C—C14C	119.7 (4)
C9B—C3B—H3B	119.8	C12C—C13C—H13C	120.2
C5B—C4B—C3B	120.7 (4)	C14C—C13C—H13C	120.2
C5B—C4B—H4B	119.7	C15C—C14C—C13C	119.8 (4)
C3B—C4B—H4B	119.7	C15C—C14C—H14C	120.1
C6B—C5B—C4B	119.9 (3)	C13C—C14C—H14C	120.1
C6B—C5B—H5B	120.1	C14C—C15C—C10C	122.4 (4)
C4B—C5B—H5B	120.1	C14C—C15C—H15C	118.8
C5B—C6B—C8B	120.0 (3)	C10C—C15C—H15C	118.8
C5B—C6B—H6B	120.0	N1C—C16C—C10C	113.3 (3)
C8B—C6B—H6B	120.0	N1C—C16C—H16C	108.9
O2B—C7B—N1B	119.9 (3)	C10C—C16C—H16C	108.9
O2B—C7B—C8B	122.4 (3)	N1C—C16C—H16D	108.9
N1B—C7B—C8B	117.6 (3)	C10C—C16C—H16D	108.9
C9B—C8B—C6B	120.7 (3)	H16C—C16C—H16D	107.7
C9B—C8B—C7B	120.9 (3)
C7A—N1A—C1A—O1A	−177.3 (3)	O2B—C7B—C8B—C6B	2.2 (5)
C16A—N1A—C1A—O1A	−0.3 (5)	N1B—C7B—C8B—C6B	−177.0 (3)
C7A—N1A—C1A—C2A	5.2 (5)	C6B—C8B—C9B—C3B	1.5 (5)
C16A—N1A—C1A—C2A	−177.7 (3)	C7B—C8B—C9B—C3B	−178.6 (3)
O1A—C1A—C2A—C9A	173.1 (3)	C6B—C8B—C9B—C2B	−178.7 (3)
N1A—C1A—C2A—C9A	−9.5 (5)	C7B—C8B—C9B—C2B	1.3 (5)
C9A—C3A—C4A—C5A	1.9 (6)	C4B—C3B—C9B—C8B	−1.8 (6)
C3A—C4A—C5A—C6A	−1.5 (6)	C4B—C3B—C9B—C2B	178.4 (4)
C4A—C5A—C6A—C8A	−0.2 (6)	C1B—C2B—C9B—C8B	−6.2 (5)
C1A—N1A—C7A—O2A	179.4 (3)	C1B—C2B—C9B—C3B	173.6 (3)
C16A—N1A—C7A—O2A	2.4 (5)	C15B—C10B—C11B—C12B	0.5 (5)
C1A—N1A—C7A—C8A	0.2 (5)	C16B—C10B—C11B—C12B	177.8 (3)
C16A—N1A—C7A—C8A	−176.8 (3)	C15B—C10B—C11B—Cl1B	−177.6 (3)
C5A—C6A—C8A—C9A	1.5 (5)	C16B—C10B—C11B—Cl1B	−0.4 (4)
C5A—C6A—C8A—C7A	−176.9 (3)	C10B—C11B—C12B—C13B	−0.4 (5)
O2A—C7A—C8A—C9A	180.0 (4)	Cl1B—C11B—C12B—C13B	177.7 (3)
N1A—C7A—C8A—C9A	−0.9 (5)	C11B—C12B—C13B—C14B	0.4 (6)
O2A—C7A—C8A—C6A	−1.7 (6)	C12B—C13B—C14B—C15B	−0.5 (6)
N1A—C7A—C8A—C6A	177.5 (3)	C13B—C14B—C15B—C10B	0.6 (6)
C6A—C8A—C9A—C3A	−1.1 (5)	C11B—C10B—C15B—C14B	−0.6 (5)
C7A—C8A—C9A—C3A	177.2 (3)	C16B—C10B—C15B—C14B	−177.9 (4)
C6A—C8A—C9A—C2A	177.8 (3)	C7B—N1B—C16B—C10B	99.4 (4)
C7A—C8A—C9A—C2A	−3.9 (5)	C11B—C10B—C16B—N1B	153.1 (3)
C4A—C3A—C9A—C8A	−0.5 (5)	C7C—N1C—C1C—O1C	177.7 (3)
C4A—C3A—C9A—C2A	−179.4 (3)	C16C—N1C—C1C—O1C	−0.2 (5)
C1A—C2A—C9A—C8A	9.0 (5)	C7C—N1C—C1C—C2C	−4.2 (5)
C1A—C2A—C9A—C3A	−172.1 (3)	C16C—N1C—C1C—C2C	177.9 (3)
C15A—C10A—C11A—C12A	1.3 (5)	O1C—C1C—C2C—C9C	−173.2 (3)
C16A—C10A—C11A—C12A	−178.2 (4)	N1C—C1C—C2C—C9C	8.8 (5)
C15A—C10A—C11A—Cl1A	−179.2 (3)	C9C—C3C—C4C—C5C	0.3 (7)
C16A—C10A—C11A—Cl1A	1.4 (5)	C3C—C4C—C5C—C6C	−0.1 (7)
C10A—C11A—C12A—C13A	0.4 (7)	C4C—C5C—C6C—C8C	0.7 (6)
Cl1A—C11A—C12A—C13A	−179.2 (4)	C1C—N1C—C7C—O2C	178.6 (3)
C11A—C12A—C13A—C14A	−1.6 (7)	C16C—N1C—C7C—O2C	−3.6 (5)
C12A—C13A—C14A—C15A	1.1 (7)	C1C—N1C—C7C—C8C	−2.3 (5)
C11A—C10A—C15A—C14A	−1.8 (6)	C16C—N1C—C7C—C8C	175.5 (3)
C16A—C10A—C15A—C14A	177.6 (4)	C5C—C6C—C8C—C9C	−1.5 (5)
C13A—C14A—C15A—C10A	0.6 (6)	C5C—C6C—C8C—C7C	179.0 (3)
C1A—N1A—C16A—C10A	80.2 (4)	O2C—C7C—C8C—C9C	−176.9 (3)
C1B—N1B—C16B—C10B	−81.8 (4)	N1C—C7C—C8C—C9C	4.0 (5)
C1C—N1C—C16C—C10C	−83.1 (4)	O2C—C7C—C8C—C6C	2.6 (5)
C15A—C10A—C16A—N1A	19.3 (5)	N1C—C7C—C8C—C6C	−176.5 (3)
C15B—C10B—C16B—N1B	−29.8 (5)	C6C—C8C—C9C—C3C	1.7 (5)
C15C—C10C—C16C—N1C	−30.8 (4)	C7C—C8C—C9C—C3C	−178.9 (3)
C7A—N1A—C16A—C10A	−102.6 (4)	C6C—C8C—C9C—C2C	−178.6 (3)
C11A—C10A—C16A—N1A	−161.4 (3)	C7C—C8C—C9C—C2C	0.9 (5)
C7B—N1B—C1B—O1B	178.4 (3)	C4C—C3C—C9C—C8C	−1.1 (6)
C16B—N1B—C1B—O1B	−0.3 (5)	C4C—C3C—C9C—C2C	179.2 (4)
C7B—N1B—C1B—C2B	−2.8 (5)	C1C—C2C—C9C—C8C	−7.2 (5)
C16B—N1B—C1B—C2B	178.5 (3)	C1C—C2C—C9C—C3C	172.5 (3)
O1B—C1B—C2B—C9B	−174.3 (3)	C15C—C10C—C11C—C12C	0.7 (5)
N1B—C1B—C2B—C9B	6.9 (5)	C16C—C10C—C11C—C12C	177.5 (3)
C9B—C3B—C4B—C5B	1.2 (6)	C15C—C10C—C11C—Cl1C	179.5 (2)
C3B—C4B—C5B—C6B	−0.3 (7)	C16C—C10C—C11C—Cl1C	−3.8 (4)
C4B—C5B—C6B—C8B	0.0 (6)	C10C—C11C—C12C—C13C	−0.3 (6)
C1B—N1B—C7B—O2B	178.6 (3)	Cl1C—C11C—C12C—C13C	−179.1 (3)
C16B—N1B—C7B—O2B	−2.8 (5)	C11C—C12C—C13C—C14C	0.0 (6)
C1B—N1B—C7B—C8B	−2.2 (5)	C12C—C13C—C14C—C15C	−0.2 (6)
C16B—N1B—C7B—C8B	176.4 (3)	C13C—C14C—C15C—C10C	0.6 (6)
C5B—C6B—C8B—C9B	−0.6 (5)	C11C—C10C—C15C—C14C	−0.9 (5)
C5B—C6B—C8B—C7B	179.4 (3)	C16C—C10C—C15C—C14C	−177.6 (3)
O2B—C7B—C8B—C9B	−177.8 (3)	C7C—N1C—C16C—C10C	98.9 (3)
N1B—C7B—C8B—C9B	3.1 (5)	C11C—C10C—C16C—N1C	152.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5A—H5A···O1C^i	0.95	2.45	3.294 (4)	148
C5C—H5C···O1B^ii	0.95	2.51	3.238 (5)	133
C2A—H2A2···O1C^iii	0.99	2.46	3.292 (5)	141
C2B—H2B2···O1B^iv	0.99	2.56	3.391 (5)	141
C5B—H5B···O1A^v	0.95	2.59	3.265 (5)	129

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

(II) N-(2-Bromo-4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione

Crystal data

C16H12BrNO2	F(000) = 664
Mr = 330.18	Dx = 1.586 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 15.847 (2) Å	Cell parameters from 25 reflections
b = 7.9190 (7) Å	θ = 5.0–10.2°
c = 11.0602 (11) Å	µ = 2.97 mm^−1
β = 94.750 (9)°	T = 293 K
V = 1383.2 (3) Å^3	Prism, colourless
Z = 4	0.35 × 0.30 × 0.30 mm

Data collection

Enraf-Nonius FR-590 diffractometer	Rint = 0.019
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.2°
Graphite monochromator	h = −18→18
non–profiled ω/2θ scans	k = 0→9
2554 measured reflections	l = 0→13
2421 independent reflections	3 standard reflections every 100 reflections
1818 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 1.02
2421 reflections	(Δ/σ)max = 0.002
182 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −0.83 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
Br1	0.18497 (3)	0.23293 (5)	0.67278 (4)	0.0643 (2)
N1	0.15445 (17)	0.1708 (4)	0.9412 (3)	0.0396 (7)
O1	0.03927 (15)	0.3324 (3)	0.8949 (2)	0.0502 (7)
O2	0.26553 (19)	0.0036 (4)	0.9991 (3)	0.0748 (10)
C1	0.1095 (2)	0.3218 (4)	0.9440 (3)	0.0377 (8)
C2	0.1520 (2)	0.4689 (5)	1.0072 (4)	0.0481 (9)
H2A	0.1132	0.5169	1.0611	0.058*
H2B	0.1616	0.5538	0.9467	0.058*
C3	0.2748 (2)	0.5659 (5)	1.1457 (4)	0.0536 (10)
H3	0.2505	0.6727	1.1456	0.064*
C4	0.3506 (2)	0.5368 (7)	1.2113 (4)	0.0645 (12)
H4	0.3774	0.6242	1.2557	0.077*
C5	0.3873 (2)	0.3804 (7)	1.2121 (4)	0.0606 (12)
H5	0.4386	0.3618	1.2571	0.073*
C6	0.3485 (3)	0.2511 (5)	1.1468 (4)	0.0533 (10)
H6	0.3736	0.1449	1.1471	0.064*
C7	0.2332 (2)	0.1397 (5)	1.0058 (3)	0.0459 (9)
C8	0.2714 (2)	0.2792 (5)	1.0797 (3)	0.0413 (8)
C9	0.2346 (2)	0.4363 (5)	1.0797 (3)	0.0406 (8)
C10	0.1205 (2)	0.0402 (4)	0.8621 (3)	0.0391 (8)
C11	0.1288 (2)	0.0497 (5)	0.7388 (3)	0.0425 (8)
C12	0.0964 (2)	−0.0765 (5)	0.6620 (4)	0.0495 (9)
H12	0.1023	−0.0688	0.5792	0.059*
C13	0.0555 (2)	−0.2129 (5)	0.7065 (4)	0.0502 (9)
C14	0.0476 (2)	−0.2220 (4)	0.8305 (4)	0.0491 (9)
H14	0.0205	−0.3144	0.8620	0.059*
C15	0.0791 (2)	−0.0966 (4)	0.9071 (4)	0.0453 (9)
H15	0.0725	−0.1039	0.9897	0.054*
C16	0.0203 (3)	−0.3502 (6)	0.6226 (5)	0.0729 (13)
H16A	−0.0331	−0.3144	0.5834	0.109*
H16B	0.0122	−0.4510	0.6685	0.109*
H16C	0.0592	−0.3725	0.5625	0.109*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0802 (4)	0.0542 (3)	0.0610 (3)	−0.0184 (2)	0.0208 (2)	−0.0017 (2)
N1	0.0401 (16)	0.0360 (15)	0.0415 (16)	0.0036 (13)	−0.0045 (13)	−0.0057 (13)
O1	0.0405 (15)	0.0467 (15)	0.0611 (17)	0.0058 (12)	−0.0096 (13)	−0.0079 (13)
O2	0.0702 (19)	0.0551 (18)	0.094 (2)	0.0302 (15)	−0.0255 (17)	−0.0209 (16)
C1	0.0379 (19)	0.0358 (17)	0.0388 (19)	0.0019 (15)	−0.0015 (16)	−0.0025 (15)
C2	0.042 (2)	0.0380 (19)	0.062 (3)	0.0027 (16)	−0.0102 (17)	−0.0098 (18)
C3	0.046 (2)	0.056 (2)	0.058 (2)	−0.0056 (18)	0.0012 (19)	−0.010 (2)
C4	0.049 (2)	0.085 (3)	0.059 (3)	−0.014 (2)	−0.006 (2)	−0.019 (2)
C5	0.041 (2)	0.092 (3)	0.046 (2)	−0.006 (2)	−0.0104 (18)	−0.001 (2)
C6	0.041 (2)	0.070 (3)	0.048 (2)	0.0097 (19)	−0.0035 (17)	0.0005 (19)
C7	0.046 (2)	0.046 (2)	0.045 (2)	0.0105 (17)	−0.0027 (16)	−0.0026 (17)
C8	0.0344 (18)	0.052 (2)	0.0373 (18)	0.0039 (15)	−0.0003 (15)	0.0012 (16)
C9	0.0341 (17)	0.048 (2)	0.0392 (19)	0.0005 (15)	−0.0015 (14)	−0.0029 (16)
C10	0.0357 (18)	0.0354 (18)	0.045 (2)	0.0059 (14)	−0.0025 (15)	−0.0032 (15)
C11	0.0406 (19)	0.0405 (19)	0.047 (2)	−0.0015 (15)	0.0058 (16)	−0.0015 (16)
C12	0.055 (2)	0.049 (2)	0.044 (2)	−0.0007 (18)	0.0029 (17)	−0.0082 (18)
C13	0.046 (2)	0.045 (2)	0.060 (2)	−0.0016 (17)	0.0020 (18)	−0.0162 (18)
C14	0.048 (2)	0.0334 (18)	0.065 (3)	−0.0022 (16)	−0.0001 (19)	0.0000 (18)
C15	0.051 (2)	0.0397 (19)	0.045 (2)	0.0079 (17)	0.0002 (16)	0.0064 (16)
C16	0.078 (3)	0.059 (3)	0.081 (3)	−0.020 (2)	0.003 (3)	−0.027 (2)

Geometric parameters (Å, º)

Br1—C11	1.881 (4)	C6—C8	1.394 (5)
N1—C1	1.393 (4)	C6—H6	0.9300
N1—C7	1.407 (5)	C7—C8	1.474 (5)
N1—C10	1.431 (4)	C8—C9	1.374 (5)
O1—C1	1.200 (4)	C10—C15	1.381 (5)
O2—C7	1.198 (4)	C10—C11	1.383 (5)
C1—C2	1.490 (5)	C11—C12	1.383 (5)
C2—C9	1.498 (5)	C12—C13	1.372 (5)
C2—H2A	0.9700	C12—H12	0.9300
C2—H2B	0.9700	C13—C14	1.389 (6)
C3—C4	1.370 (6)	C13—C16	1.506 (6)
C3—C9	1.385 (5)	C14—C15	1.372 (5)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.368 (7)	C15—H15	0.9300
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.369 (6)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C1—N1—C7	124.9 (3)	C6—C8—C7	118.5 (3)
C1—N1—C10	117.8 (3)	C8—C9—C3	119.6 (3)
C7—N1—C10	117.2 (3)	C8—C9—C2	120.5 (3)
O1—C1—N1	120.4 (3)	C3—C9—C2	119.9 (3)
O1—C1—C2	121.6 (3)	C15—C10—C11	119.0 (3)
N1—C1—C2	118.0 (3)	C15—C10—N1	120.8 (3)
C1—C2—C9	117.2 (3)	C11—C10—N1	120.1 (3)
C1—C2—H2A	108.0	C10—C11—C12	120.3 (3)
C9—C2—H2A	108.0	C10—C11—Br1	120.8 (3)
C1—C2—H2B	108.0	C12—C11—Br1	118.9 (3)
C9—C2—H2B	108.0	C13—C12—C11	120.8 (4)
H2A—C2—H2B	107.2	C13—C12—H12	119.6
C4—C3—C9	120.0 (4)	C11—C12—H12	119.6
C4—C3—H3	120.0	C12—C13—C14	118.6 (3)
C9—C3—H3	120.0	C12—C13—C16	120.6 (4)
C5—C4—C3	120.6 (4)	C14—C13—C16	120.8 (4)
C5—C4—H4	119.7	C15—C14—C13	120.9 (4)
C3—C4—H4	119.7	C15—C14—H14	119.5
C6—C5—C4	120.1 (4)	C13—C14—H14	119.5
C6—C5—H5	119.9	C14—C15—C10	120.3 (4)
C4—C5—H5	119.9	C14—C15—H15	119.8
C5—C6—C8	119.8 (4)	C10—C15—H15	119.8
C5—C6—H6	120.1	C13—C16—H16A	109.5
C8—C6—H6	120.1	C13—C16—H16B	109.5
O2—C7—N1	119.5 (3)	H16A—C16—H16B	109.5
O2—C7—C8	123.4 (3)	C13—C16—H16C	109.5
N1—C7—C8	117.1 (3)	H16A—C16—H16C	109.5
C9—C8—C6	119.9 (3)	H16B—C16—H16C	109.5
C9—C8—C7	121.6 (3)
C7—N1—C1—O1	−173.2 (3)	C7—C8—C9—C2	2.2 (5)
C10—N1—C1—O1	10.2 (5)	C4—C3—C9—C8	−0.5 (6)
C7—N1—C1—C2	8.1 (5)	C4—C3—C9—C2	−179.5 (3)
C10—N1—C1—C2	−168.5 (3)	C1—C2—C9—C8	4.5 (5)
O1—C1—C2—C9	171.9 (3)	C1—C2—C9—C3	−176.5 (3)
N1—C1—C2—C9	−9.4 (5)	C1—N1—C10—C15	−102.7 (4)
C9—C3—C4—C5	0.1 (7)	C7—N1—C10—C15	80.4 (4)
C3—C4—C5—C6	0.2 (7)	C1—N1—C10—C11	77.3 (4)
C4—C5—C6—C8	−0.2 (6)	C7—N1—C10—C11	−99.5 (4)
C1—N1—C7—O2	178.3 (4)	C15—C10—C11—C12	−0.2 (5)
C10—N1—C7—O2	−5.1 (5)	N1—C10—C11—C12	179.7 (3)
C1—N1—C7—C8	−1.4 (5)	C15—C10—C11—Br1	−179.7 (2)
C10—N1—C7—C8	175.2 (3)	N1—C10—C11—Br1	0.2 (4)
C5—C6—C8—C9	−0.2 (6)	C10—C11—C12—C13	0.0 (6)
C5—C6—C8—C7	177.2 (4)	Br1—C11—C12—C13	179.5 (3)
O2—C7—C8—C9	176.4 (4)	C11—C12—C13—C14	−0.2 (6)
N1—C7—C8—C9	−4.0 (5)	C11—C12—C13—C16	−180.0 (4)
O2—C7—C8—C6	−1.0 (6)	C12—C13—C14—C15	0.7 (6)
N1—C7—C8—C6	178.6 (3)	C16—C13—C14—C15	−179.6 (4)
C6—C8—C9—C3	0.6 (6)	C13—C14—C15—C10	−0.9 (6)
C7—C8—C9—C3	−176.8 (4)	C11—C10—C15—C14	0.7 (5)
C6—C8—C9—C2	179.5 (4)	N1—C10—C15—C14	−179.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.93	2.53	2.808 (5)	98
C5—H5···O1^i	0.93	2.61	3.451 (5)	151

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

(III) N-(2,3-Dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione

Crystal data

C15H9Cl2NO2	F(000) = 624
Mr = 306.13	Dx = 1.561 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.6702 (8) Å	Cell parameters from 25 reflections
b = 6.1560 (5) Å	θ = 6.2–10.3°
c = 14.5889 (7) Å	µ = 0.50 mm^−1
β = 112.236 (4)°	T = 293 K
V = 1302.67 (14) Å^3	Prism, colourless
Z = 4	0.25 × 0.25 × 0.20 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	1872 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 25.0°, θmin = 1.4°
non–profiled ω/2θ scans	h = −18→17
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968)	k = 0→7
Tmin = 0.886, Tmax = 0.907	l = 0→17
2391 measured reflections	3 standard reflections every 100 reflections
2287 independent reflections	intensity decay: 1%

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.156	H-atom parameters constrained
S = 1.01
2287 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.23 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
Cl1	0.23957 (5)	0.39980 (12)	0.61118 (6)	0.0561 (3)
Cl2	0.37167 (5)	0.46466 (14)	0.49537 (5)	0.0618 (3)
N1	0.26384 (13)	0.7203 (3)	0.76998 (15)	0.0387 (5)
O1	0.36347 (14)	0.4587 (4)	0.85483 (17)	0.0669 (6)
O2	0.16720 (14)	0.9913 (4)	0.68980 (16)	0.0610 (6)
C1	0.29209 (18)	0.5527 (4)	0.83976 (19)	0.0449 (6)
C2	0.22926 (19)	0.4909 (4)	0.8906 (2)	0.0500 (7)
H2A	0.2665	0.4651	0.9599	0.060*
H2B	0.1999	0.3544	0.8628	0.060*
C3	0.10494 (19)	0.6249 (5)	0.9445 (2)	0.0514 (7)
H3	0.1186	0.5118	0.9902	0.062*
C4	0.03460 (19)	0.7662 (5)	0.9364 (2)	0.0580 (8)
H4	0.0006	0.7473	0.9761	0.070*
C5	0.0141 (2)	0.9361 (5)	0.8698 (2)	0.0544 (7)
H5	−0.0336	1.0313	0.8647	0.065*
C6	0.06419 (17)	0.9646 (5)	0.8110 (2)	0.0476 (6)
H6	0.0507	1.0796	0.7664	0.057*
C7	0.18721 (16)	0.8548 (4)	0.75383 (18)	0.0399 (6)
C8	0.13555 (15)	0.8206 (4)	0.81842 (17)	0.0390 (6)
C9	0.15579 (16)	0.6493 (4)	0.88512 (19)	0.0415 (6)
C10	0.31925 (15)	0.7597 (4)	0.71221 (18)	0.0393 (6)
C11	0.31480 (16)	0.6159 (4)	0.63733 (18)	0.0386 (5)
C12	0.37232 (17)	0.6471 (4)	0.58559 (18)	0.0430 (6)
C13	0.43133 (18)	0.8229 (5)	0.6068 (2)	0.0481 (6)
H13	0.4695	0.8440	0.5719	0.058*
C14	0.43348 (18)	0.9662 (5)	0.6795 (2)	0.0509 (7)
H14	0.4728	1.0854	0.6930	0.061*
C15	0.37803 (18)	0.9364 (4)	0.7333 (2)	0.0469 (6)
H15	0.3803	1.0338	0.7829	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0558 (5)	0.0490 (4)	0.0727 (5)	−0.0171 (3)	0.0347 (4)	−0.0118 (3)
Cl2	0.0694 (5)	0.0705 (5)	0.0587 (5)	−0.0082 (4)	0.0391 (4)	−0.0152 (3)
N1	0.0362 (10)	0.0401 (11)	0.0461 (11)	0.0027 (8)	0.0228 (9)	0.0046 (9)
O1	0.0566 (12)	0.0795 (15)	0.0765 (15)	0.0304 (11)	0.0388 (11)	0.0307 (12)
O2	0.0569 (12)	0.0636 (13)	0.0757 (14)	0.0187 (10)	0.0399 (11)	0.0303 (11)
C1	0.0411 (13)	0.0487 (14)	0.0487 (14)	0.0067 (11)	0.0215 (11)	0.0068 (11)
C2	0.0494 (15)	0.0479 (15)	0.0598 (16)	0.0066 (12)	0.0286 (13)	0.0155 (13)
C3	0.0531 (15)	0.0593 (16)	0.0484 (15)	−0.0003 (13)	0.0268 (12)	0.0069 (13)
C4	0.0512 (16)	0.078 (2)	0.0570 (16)	−0.0054 (14)	0.0342 (13)	−0.0084 (16)
C5	0.0461 (15)	0.0649 (18)	0.0604 (17)	0.0073 (13)	0.0294 (13)	−0.0059 (15)
C6	0.0423 (14)	0.0486 (14)	0.0549 (16)	0.0057 (11)	0.0217 (12)	0.0000 (12)
C7	0.0373 (12)	0.0388 (13)	0.0458 (13)	0.0011 (10)	0.0183 (10)	0.0037 (11)
C8	0.0345 (12)	0.0418 (13)	0.0423 (13)	−0.0009 (9)	0.0164 (10)	−0.0016 (10)
C9	0.0372 (12)	0.0446 (14)	0.0445 (13)	−0.0022 (11)	0.0175 (10)	0.0013 (11)
C10	0.0349 (11)	0.0408 (13)	0.0466 (13)	0.0035 (10)	0.0204 (10)	0.0042 (11)
C11	0.0350 (12)	0.0381 (12)	0.0445 (13)	−0.0013 (10)	0.0172 (10)	0.0031 (10)
C12	0.0392 (12)	0.0505 (14)	0.0425 (13)	0.0012 (11)	0.0189 (10)	0.0001 (11)
C13	0.0413 (13)	0.0603 (17)	0.0495 (14)	−0.0047 (12)	0.0248 (11)	0.0065 (12)
C14	0.0451 (15)	0.0512 (15)	0.0593 (17)	−0.0144 (12)	0.0231 (13)	−0.0011 (13)
C15	0.0459 (14)	0.0460 (14)	0.0530 (15)	−0.0062 (11)	0.0233 (12)	−0.0045 (12)

Geometric parameters (Å, º)

Cl1—C11	1.722 (2)	C5—C6	1.376 (4)
Cl2—C12	1.727 (3)	C5—H5	0.9300
N1—C1	1.398 (3)	C6—C8	1.399 (3)
N1—C7	1.403 (3)	C6—H6	0.9300
N1—C10	1.441 (3)	C7—C8	1.471 (3)
O1—C1	1.203 (3)	C8—C9	1.387 (4)
O2—C7	1.207 (3)	C10—C11	1.387 (3)
C1—C2	1.489 (4)	C10—C15	1.382 (4)
C2—C9	1.488 (4)	C11—C12	1.391 (3)
C2—H2A	0.9700	C12—C13	1.380 (4)
C2—H2B	0.9700	C13—C14	1.370 (4)
C3—C4	1.374 (4)	C13—H13	0.9300
C3—C9	1.390 (4)	C14—C15	1.386 (4)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.381 (4)	C15—H15	0.9300
C4—H4	0.9300
C1—N1—C7	124.9 (2)	N1—C7—C8	116.8 (2)
C1—N1—C10	117.07 (19)	C9—C8—C6	120.0 (2)
C7—N1—C10	117.98 (19)	C9—C8—C7	121.5 (2)
O1—C1—N1	120.3 (2)	C6—C8—C7	118.5 (2)
O1—C1—C2	122.0 (2)	C8—C9—C3	119.1 (2)
N1—C1—C2	117.7 (2)	C8—C9—C2	120.2 (2)
C1—C2—C9	116.7 (2)	C3—C9—C2	120.7 (2)
C1—C2—H2A	108.1	C11—C10—C15	120.5 (2)
C9—C2—H2A	108.1	C11—C10—N1	119.4 (2)
C1—C2—H2B	108.1	C15—C10—N1	120.0 (2)
C9—C2—H2B	108.1	C10—C11—C12	119.3 (2)
H2A—C2—H2B	107.3	C10—C11—Cl1	119.59 (18)
C4—C3—C9	120.6 (3)	C12—C11—Cl1	121.1 (2)
C4—C3—H3	119.7	C13—C12—C11	120.2 (2)
C9—C3—H3	119.7	C13—C12—Cl2	119.4 (2)
C3—C4—C5	120.4 (2)	C11—C12—Cl2	120.4 (2)
C3—C4—H4	119.8	C14—C13—C12	119.8 (2)
C5—C4—H4	119.8	C14—C13—H13	120.1
C6—C5—C4	120.0 (3)	C12—C13—H13	120.1
C6—C5—H5	120.0	C13—C14—C15	121.0 (2)
C4—C5—H5	120.0	C13—C14—H14	119.5
C5—C6—C8	120.0 (3)	C15—C14—H14	119.5
C5—C6—H6	120.0	C10—C15—C14	119.1 (2)
C8—C6—H6	120.0	C10—C15—H15	120.5
O2—C7—N1	119.7 (2)	C14—C15—H15	120.5
O2—C7—C8	123.4 (2)
C7—N1—C1—O1	−173.1 (3)	C4—C3—C9—C8	1.0 (4)
C10—N1—C1—O1	5.4 (4)	C4—C3—C9—C2	−177.3 (3)
C7—N1—C1—C2	9.3 (4)	C1—C2—C9—C8	13.5 (4)
C10—N1—C1—C2	−172.2 (2)	C1—C2—C9—C3	−168.3 (2)
O1—C1—C2—C9	165.6 (3)	C1—N1—C10—C11	74.0 (3)
N1—C1—C2—C9	−16.9 (4)	C7—N1—C10—C11	−107.3 (3)
C9—C3—C4—C5	−0.7 (4)	C1—N1—C10—C15	−104.3 (3)
C3—C4—C5—C6	0.0 (4)	C7—N1—C10—C15	74.4 (3)
C4—C5—C6—C8	0.4 (4)	C15—C10—C11—C12	2.1 (4)
C1—N1—C7—O2	−178.0 (3)	N1—C10—C11—C12	−176.2 (2)
C10—N1—C7—O2	3.5 (4)	C15—C10—C11—Cl1	−178.90 (19)
C1—N1—C7—C8	2.5 (4)	N1—C10—C11—Cl1	2.8 (3)
C10—N1—C7—C8	−176.0 (2)	C10—C11—C12—C13	−1.8 (4)
C5—C6—C8—C9	−0.1 (4)	Cl1—C11—C12—C13	179.2 (2)
C5—C6—C8—C7	179.5 (2)	C10—C11—C12—Cl2	177.39 (19)
O2—C7—C8—C9	174.1 (3)	Cl1—C11—C12—Cl2	−1.6 (3)
N1—C7—C8—C9	−6.4 (3)	C11—C12—C13—C14	0.4 (4)
O2—C7—C8—C6	−5.4 (4)	Cl2—C12—C13—C14	−178.8 (2)
N1—C7—C8—C6	174.0 (2)	C12—C13—C14—C15	0.8 (4)
C6—C8—C9—C3	−0.6 (4)	C11—C10—C15—C14	−0.9 (4)
C7—C8—C9—C3	179.9 (2)	N1—C10—C15—C14	177.4 (2)
C6—C8—C9—C2	177.7 (2)	C13—C14—C15—C10	−0.6 (4)
C7—C8—C9—C2	−1.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1^i	0.93	2.52	3.161 (3)	126

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