The 1:1 inclusion compounds zolmitriptan-benzene and zolmitriptan-phenol

In the benzene and phenol solvates of (S)-4-{3-[2-(dimethyl­amino)eth­yl]-1H-indol-5-ylmeth­yl}­oxazolidin-2-one, viz. C₁₆H₂₁N₃O₂·C₆H₆, (I), and C₁₆H₂₁N₃O₂·C₆H₅OH, (II), the host mol­ecule has three linked residues, namely a planar indole ring system, an ethyl­amine side chain and an oxazolidinone system. It has comparable features to that of sumatriptan, although the side-chain orientations of (I) and (II) differ from those of sumatriptan. Both (I) and (II) have host-guest-type structures. The host mol­ecule in (I) and (II) has an L-shaped form, with the oxazolidinone ring occupying the base and the remainder of the mol­ecule forming the upright section. In (I), each benzene guest mol­ecule is surrounded by four host mol­ecules, and these mol­ecules are linked by a combination of N-H...N, N-H...O and C-H...O hydrogen bonds into chains of edge-fused R₄⁴(33) rings. In (II), two independent mol­ecules are present in the asymmetric unit, with similar conformations. The heterocyclic components are connected through N-H...N, N-H...O and C-H...O inter­actions to form chains of edge-fused R₆⁴(38) rings, from which the phenol guest mol­ecules are pendent, linked by O-H...O hydrogen bonds. The structures are further stabilized by extensive C-­H...[pi] inter­actions.

S1. Comment

Zolmitriptan is an effective drug for the treatment of migraine headaches, which are believed to result from dilation of the blood vessels in the brain. The structure and its mechanism of action are comparable to that of sumatriptan (Ravikumar et al., 2004). We have previously published the crystal structure of zolmitriptan (Ravikumar et al., 2007) and its chloroform solvate (Sridhar et al., 2007). In an attempt to understand the effect on drug polymorphism in the light of host–guest structural mechanisms, we crystallized two inclusion compounds and their crystal structures are presented here.

The molecule of zolmitriptan consists of three linked residues, viz. a planar indole ring system, an ethylamine side chain and an oxazolidinone unit. Compound (I) contains molecules of zolmitriptan (host) and benzene (guest) (Fig. 1). Compound (II) consists of two independent molecules (A and B) of zolmitriptan (host) and phenol (guest) (1:1) in the asymmetric unit (Fig. 2). In both structures, the host molecule aquires an L-shaped conformation, with the oxazolidinone ring occupying the base and the rest of the molecule forming the upright section. In contrast, some relatively large conformational differences [in compounds (I) and (II) {unclear whether (I) and (II) are different from each other AND from the parent, or if (I) and (II) are similar to each other but both are different from the parent}] are observed in both the side chains, when compared with the parent (pure) zolmitriptan and its chloroform solvate. Interestingly, the indole ring system remains planar in all the structures. Another noteworthy point is that the oxazolidinone ring in the present structures is almost planar, unlike in the parent molecule and its chloroform solvate, where the ring takes a twist conformation. Furthermore, the orientation of the oxazolidinone side chain is synclinical with respect to the indole ring system in (I) and (II) (Tables 1 and 3), whereas, in pure zolmitriptan, the value deviates significantly [C4—C5—C13—C14 = 95.6 (3)°]. The ethylamine side chain of the host molecule has an extended conformation in both compounds (I) and (II). This can be seen clearly in terms of their C2—C9—C10—N2 torsion angle (Tables 1 and 3). In (I), with respect to the indole ring system, the planes of the ethylamine and the oxazolidinone ring, make dihedral angles of 53.7 (1) and 64.4 (1)°, respectively [54.0 (1) and 64.8 (1) for molecule A of (II), and 54.0 (1) and 62.8 (1)° for molecule B]. Similarly, the dihedral angle between the planes of the oxazolidinone ring and the ethylamine moiety is 74.4 (1)° (75.9 (1) and 74.4 (1)° respectively for compound (II)). Again, these values are predominantly different from the pure zolmitriptan (30.0 (1)°). This significant conformational change could be attributed to the guest molecules present in the respective compounds. An overlay fitting of the indole ring system of compounds (I) and (II) along with pure zolmitriptan and its chloroform solvate is shown in Fig. 3.

In both the structures, oxazolidinone atom N3 acts as a hydrogen-bond donor to ethylamine atom N2 (Tables 2 and 4), so forming continuous screw-symmetric helical chains of C11 type (Bernstein et al., 1995) along the a axis (Figs. 4 and 5). In (I), these chains are further connected into R⁴₄(33) rings through N—H···O and C—H···O hydrogen bonds along the c axis, forming a supramolecular network (Fig. 4). The guest benzene molecules are involved in C—H···π interactions with the indole ring system of the host molecules (Table 2). In (II), within the asymmetric unit, atom O3A of the guest phenol molecule A acts as a hydrogen-bond donor, via H3A, to hydroxy atom O3B of phenol molecule B, and the pendent guest molecules are linked to the ketone atom O2B of the host molecule B via atom H3C (Table 4). In (II), these A and B chains are further interconnected via N—H···O and C—H···O interactions. The combination of these two independent molecules (A and B) then generates two-dimensional edge-fused R⁴₆ (38) rings. This two-dimensional supramolecular network is further strengthened by extensive C—H···π interactions (Table 4). The centroids of the guest molecules (C17–C22 of A/B) lie 2.81 and 2.86 Å, respectively, from the H atoms of the pyrrole rings of the indole ring systems (H1A and H1D). These values agree well with those expected for typical C—H···π interactions (Guo et al., 2005; Huang et al., 2001), demonstrating C—H···π interactions in the inclusion compound. The C—H···π interaction in (I) and (II) are rather weak; however, they play a significant role in maintaining the conformational changes in the host molecules.

In conclusion, zolmitriptan produces inclusion compounds when it crystallizes from chloroform (Sridhar et al., 2007), benzene and phenol (the present work), whereas crystallization from methanol (Ravikumar et al., 2007), which presumably is not a preferred guest, does not produce an inclusion compound.

Related literature

For related literature, see: Bernstein et al. (1995); Guo et al. (2005); Huang et al. (2001); Ravikumar (2004); Ravikumar et al. (2007); Sridhar et al. (2007).

S2. Experimental

Crystals of the title compounds were grown from benzene [for (I)] and phenol [for (II)] solutions by slow evaporation of zolmitriptan (1:1).

S3. Refinement

H atoms attached to N and O atoms were located in a difference density map and refined isotropically. All other H atoms were placed in geometrycally idealized positions and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å, and with U_iso(H)=1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for all other H atoms. In the compound (I), the geometries of the atoms (C17—C22) were restrained, where distances were set to a target value of 1.39 Å. Distance restraints were also applied to the H atoms of the hydroxy groups in the compound (II). In the absence of significant anomalous scattering effects, Friedel pairs were merged. The absolute configuration of zolmitriptan was known in advance.

Computing details

For both compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (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: SHELXL97 and PARST (Nardelli, 1995).

Figures

	Fig. 1. The asymmetric unit of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The independent components of (II), showing the atom labelling scheme and the O—H···O hydrogen bonding (dashed lines) within the asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 3. A least-squares fit of (I) [labelled (2); green in the online version of the journal; r.m.s. deviation 0.0315 Å] and (II) [red online; (3); 0.0311 Å] along with pure zolmitriptan [blue online; (1)] and its chloroform solvate [yellow online; (4); 0.0344 Å] based on atoms C1–C8/N1.
	Fig. 4. Part of the crystal structure of (II), highlighting the formation of a chain of R^44(33) e dge-fused rings along the b axis. Dashed lines indicate hydrogen bonds. For the sake of clarity, H atoms not involved in the motifs have been omitted.
	Fig. 5. Part of the crystal structure of (II), highlighting the formation of a chain of R^46 (38) e dge-fused rings along the a axis. Dashed lines indicate hydrogen bonds. For the sake of clarity, H atoms not involved in the motifs have been omitted.

(I) (S)-4-{3-[2-(dimethylamino)ethyl]-1H-indol-5- ylmethyl}oxazolidin-2-one benzene solvate

Crystal data

C16H21N3O2·C6H6	Dx = 1.178 Mg m^−3
Mr = 365.47	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 8329 reflections
a = 8.6938 (5) Å	θ = 2.6–27.2°
b = 12.1331 (7) Å	µ = 0.08 mm^−1
c = 19.5321 (12) Å	T = 273 K
V = 2060.3 (2) Å^3	Needles, colourless
Z = 4	0.22 × 0.17 × 0.15 mm
F(000) = 784

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1995 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω scans	h = −10→10
15000 measured reflections	k = −14→14
2097 independent reflections	l = −23→23

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.29	w = 1/[σ^2(Fo^2) + (0.0599P)^2 + 0.1882P] where P = (Fo^2 + 2Fc^2)/3
2097 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.20 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	0.6871 (3)	0.46682 (18)	0.58334 (11)	0.0476 (5)
H1	0.7631	0.4265	0.6056	0.057*
C2	0.6908 (3)	0.49690 (18)	0.51596 (10)	0.0429 (5)
C3	0.5517 (2)	0.55737 (17)	0.50370 (10)	0.0391 (5)
C4	0.4911 (2)	0.61075 (18)	0.44644 (10)	0.0408 (5)
H4	0.5430	0.6074	0.4049	0.049*
C5	0.3553 (3)	0.66813 (18)	0.45102 (11)	0.0435 (5)
C6	0.2758 (3)	0.6704 (2)	0.51412 (12)	0.0513 (6)
H6	0.1837	0.7090	0.5172	0.062*
C7	0.3313 (3)	0.6170 (2)	0.57126 (11)	0.0502 (6)
H7	0.2773	0.6183	0.6124	0.060*
C8	0.4704 (3)	0.56099 (18)	0.56572 (10)	0.0423 (5)
C9	0.8104 (3)	0.4744 (2)	0.46281 (12)	0.0562 (6)
H9A	0.8388	0.5435	0.4412	0.067*
H9B	0.7663	0.4272	0.4279	0.067*
C10	0.9545 (3)	0.42004 (19)	0.49074 (11)	0.0446 (5)
H10A	1.0015	0.4688	0.5241	0.053*
H10B	0.9258	0.3527	0.5142	0.053*
C11	1.2098 (3)	0.3574 (2)	0.46999 (15)	0.0636 (7)
H11A	1.2468	0.4138	0.5003	0.095*
H11B	1.2854	0.3433	0.4353	0.095*
H11C	1.1910	0.2911	0.4955	0.095*
C12	1.0116 (3)	0.3079 (2)	0.39179 (15)	0.0649 (7)
H12A	1.0937	0.2847	0.3622	0.097*
H12B	0.9285	0.3363	0.3647	0.097*
H12C	0.9760	0.2461	0.4181	0.097*
C13	0.2944 (3)	0.72946 (19)	0.38947 (12)	0.0506 (5)
H13A	0.3665	0.7201	0.3520	0.061*
H13B	0.2909	0.8074	0.4004	0.061*
C14	0.1368 (3)	0.69437 (18)	0.36509 (12)	0.0474 (5)
H14	0.0596	0.7106	0.4003	0.057*
C15	0.0920 (4)	0.7500 (2)	0.29724 (13)	0.0603 (7)
H15A	−0.0038	0.7902	0.3022	0.072*
H15B	0.1715	0.8010	0.2827	0.072*
C16	0.0922 (3)	0.5648 (2)	0.28072 (11)	0.0494 (5)
N1	0.5545 (2)	0.50487 (16)	0.61341 (10)	0.0482 (5)
N2	1.0674 (2)	0.39388 (15)	0.43797 (10)	0.0452 (4)
N3	0.1285 (3)	0.57960 (16)	0.34577 (10)	0.0535 (5)
O1	0.0754 (2)	0.66264 (14)	0.24893 (8)	0.0610 (5)
O2	0.0758 (3)	0.47902 (15)	0.24963 (9)	0.0706 (6)
H1N	0.521 (3)	0.498 (2)	0.6582 (15)	0.059 (7)*
H3N	0.120 (3)	0.528 (2)	0.3747 (14)	0.058 (8)*
C17	0.3679 (9)	0.2540 (6)	0.2754 (4)	0.158 (3)
H17	0.3114	0.3183	0.2692	0.190*
C18	0.4968 (10)	0.2524 (6)	0.3174 (4)	0.179 (3)
H18	0.5272	0.3161	0.3402	0.215*
C19	0.5801 (7)	0.1556 (8)	0.3253 (3)	0.158 (3)
H19	0.6678	0.1544	0.3525	0.190*
C20	0.5313 (7)	0.0608 (6)	0.2920 (3)	0.153 (3)
H20	0.5881	−0.0035	0.2978	0.184*
C21	0.4018 (8)	0.0571 (5)	0.2505 (3)	0.148 (2)
H21	0.3686	−0.0073	0.2294	0.177*
C22	0.3256 (6)	0.1569 (7)	0.2428 (3)	0.148 (3)
H22	0.2406	0.1588	0.2140	0.177*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0544 (13)	0.0471 (12)	0.0414 (10)	0.0043 (10)	−0.0049 (10)	0.0035 (9)
C2	0.0455 (11)	0.0441 (11)	0.0392 (10)	0.0015 (10)	−0.0012 (9)	−0.0005 (9)
C3	0.0406 (10)	0.0399 (10)	0.0367 (10)	−0.0043 (9)	−0.0003 (8)	−0.0040 (8)
C4	0.0421 (10)	0.0454 (11)	0.0350 (10)	−0.0035 (9)	−0.0022 (9)	−0.0015 (9)
C5	0.0446 (11)	0.0421 (11)	0.0439 (11)	−0.0042 (9)	−0.0062 (9)	−0.0053 (9)
C6	0.0452 (12)	0.0549 (13)	0.0539 (13)	0.0061 (11)	−0.0023 (11)	−0.0125 (11)
C7	0.0493 (12)	0.0598 (13)	0.0416 (11)	−0.0006 (11)	0.0069 (10)	−0.0109 (10)
C8	0.0475 (11)	0.0443 (11)	0.0351 (10)	−0.0053 (10)	−0.0004 (9)	−0.0038 (9)
C9	0.0533 (13)	0.0717 (16)	0.0437 (11)	0.0155 (12)	0.0031 (11)	0.0064 (11)
C10	0.0457 (11)	0.0452 (11)	0.0428 (11)	0.0030 (10)	−0.0023 (9)	0.0011 (9)
C11	0.0470 (13)	0.0700 (16)	0.0738 (17)	0.0131 (13)	−0.0032 (13)	0.0006 (14)
C12	0.0664 (16)	0.0591 (14)	0.0692 (15)	0.0031 (13)	0.0010 (14)	−0.0193 (13)
C13	0.0522 (12)	0.0423 (11)	0.0572 (13)	0.0021 (10)	−0.0093 (11)	0.0015 (10)
C14	0.0502 (12)	0.0431 (11)	0.0489 (12)	0.0088 (10)	−0.0082 (10)	−0.0043 (10)
C15	0.0708 (16)	0.0484 (13)	0.0615 (14)	0.0064 (13)	−0.0201 (14)	0.0024 (11)
C16	0.0567 (13)	0.0507 (12)	0.0408 (11)	−0.0005 (11)	−0.0086 (10)	0.0008 (10)
N1	0.0570 (11)	0.0543 (10)	0.0332 (9)	−0.0006 (10)	0.0033 (9)	0.0023 (8)
N2	0.0446 (10)	0.0428 (9)	0.0481 (10)	0.0034 (8)	0.0003 (8)	−0.0009 (8)
N3	0.0786 (14)	0.0428 (10)	0.0392 (10)	−0.0066 (10)	−0.0131 (10)	0.0046 (8)
O1	0.0813 (12)	0.0579 (10)	0.0437 (9)	0.0075 (9)	−0.0162 (9)	0.0069 (8)
O2	0.1059 (16)	0.0572 (10)	0.0487 (9)	−0.0042 (11)	−0.0198 (11)	−0.0082 (8)
C17	0.158 (6)	0.150 (6)	0.166 (6)	0.050 (5)	0.084 (5)	0.054 (5)
C18	0.191 (8)	0.198 (8)	0.147 (6)	−0.050 (7)	0.086 (6)	0.013 (6)
C19	0.097 (3)	0.296 (10)	0.081 (3)	−0.006 (6)	0.025 (3)	0.024 (5)
C20	0.133 (5)	0.230 (8)	0.097 (3)	0.082 (5)	0.040 (3)	0.049 (4)
C21	0.158 (6)	0.179 (6)	0.105 (4)	0.015 (5)	0.049 (4)	0.017 (4)
C22	0.083 (3)	0.255 (8)	0.105 (4)	0.037 (5)	0.035 (3)	0.064 (5)

Geometric parameters (Å, º)

C1—C2	1.366 (3)	C12—H12B	0.9600
C1—N1	1.374 (3)	C12—H12C	0.9600
C1—H1	0.9300	C13—C14	1.512 (3)
C2—C3	1.435 (3)	C13—H13A	0.9700
C2—C9	1.494 (3)	C13—H13B	0.9700
C3—C4	1.396 (3)	C14—N3	1.445 (3)
C3—C8	1.403 (3)	C14—C15	1.537 (3)
C4—C5	1.373 (3)	C14—H14	0.9800
C4—H4	0.9300	C15—O1	1.427 (3)
C5—C6	1.413 (3)	C15—H15A	0.9700
C5—C13	1.510 (3)	C15—H15B	0.9700
C6—C7	1.378 (3)	C16—O2	1.213 (3)
C6—H6	0.9300	C16—N3	1.321 (3)
C7—C8	1.391 (3)	C16—O1	1.348 (3)
C7—H7	0.9300	N1—H1N	0.93 (3)
C8—N1	1.366 (3)	N3—H3N	0.84 (3)
C9—C10	1.518 (3)	C17—C22	1.388 (11)
C9—H9A	0.9700	C17—C18	1.389 (11)
C9—H9B	0.9700	C17—H17	0.9300
C10—N2	1.458 (3)	C18—C19	1.388 (12)
C10—H10A	0.9700	C18—H18	0.9300
C10—H10B	0.9700	C19—C20	1.388 (11)
C11—N2	1.456 (3)	C19—H19	0.9300
C11—H11A	0.9600	C20—C21	1.388 (9)
C11—H11B	0.9600	C20—H20	0.9300
C11—H11C	0.9600	C21—C22	1.388 (10)
C12—N2	1.462 (3)	C21—H21	0.9300
C12—H12A	0.9600	C22—H22	0.9300
C2—C1—N1	110.0 (2)	C5—C13—H13A	108.4
C2—C1—H1	125.0	C14—C13—H13A	108.4
N1—C1—H1	125.0	C5—C13—H13B	108.4
C1—C2—C3	106.1 (2)	C14—C13—H13B	108.4
C1—C2—C9	129.6 (2)	H13A—C13—H13B	107.5
C3—C2—C9	124.32 (19)	N3—C14—C13	113.5 (2)
C4—C3—C8	119.15 (19)	N3—C14—C15	100.69 (18)
C4—C3—C2	133.58 (19)	C13—C14—C15	112.2 (2)
C8—C3—C2	107.25 (18)	N3—C14—H14	110.0
C5—C4—C3	120.50 (19)	C13—C14—H14	110.0
C5—C4—H4	119.8	C15—C14—H14	110.0
C3—C4—H4	119.8	O1—C15—C14	105.64 (18)
C4—C5—C6	119.2 (2)	O1—C15—H15A	110.6
C4—C5—C13	120.0 (2)	C14—C15—H15A	110.6
C6—C5—C13	120.9 (2)	O1—C15—H15B	110.6
C7—C6—C5	121.7 (2)	C14—C15—H15B	110.6
C7—C6—H6	119.1	H15A—C15—H15B	108.7
C5—C6—H6	119.1	O2—C16—N3	128.8 (2)
C6—C7—C8	118.1 (2)	O2—C16—O1	120.80 (19)
C6—C7—H7	121.0	N3—C16—O1	110.4 (2)
C8—C7—H7	121.0	C8—N1—C1	108.97 (18)
N1—C8—C7	131.0 (2)	C8—N1—H1N	121.4 (17)
N1—C8—C3	107.67 (19)	C1—N1—H1N	129.6 (17)
C7—C8—C3	121.4 (2)	C11—N2—C10	109.56 (19)
C2—C9—C10	113.83 (19)	C11—N2—C12	109.3 (2)
C2—C9—H9A	108.8	C10—N2—C12	111.6 (2)
C10—C9—H9A	108.8	C16—N3—C14	113.2 (2)
C2—C9—H9B	108.8	C16—N3—H3N	121.6 (18)
C10—C9—H9B	108.8	C14—N3—H3N	122.7 (17)
H9A—C9—H9B	107.7	C16—O1—C15	109.81 (17)
N2—C10—C9	113.35 (18)	C22—C17—C18	118.2 (7)
N2—C10—H10A	108.9	C22—C17—H17	120.9
C9—C10—H10A	108.9	C18—C17—H17	120.9
N2—C10—H10B	108.9	C19—C18—C17	119.9 (7)
C9—C10—H10B	108.9	C19—C18—H18	120.1
H10A—C10—H10B	107.7	C17—C18—H18	120.1
N2—C11—H11A	109.5	C20—C19—C18	119.3 (6)
N2—C11—H11B	109.5	C20—C19—H19	120.3
H11A—C11—H11B	109.5	C18—C19—H19	120.3
N2—C11—H11C	109.5	C19—C20—C21	123.2 (6)
H11A—C11—H11C	109.5	C19—C20—H20	118.4
H11B—C11—H11C	109.5	C21—C20—H20	118.4
N2—C12—H12A	109.5	C20—C21—C22	114.9 (5)
N2—C12—H12B	109.5	C20—C21—H21	122.5
H12A—C12—H12B	109.5	C22—C21—H21	122.5
N2—C12—H12C	109.5	C21—C22—C17	124.4 (6)
H12A—C12—H12C	109.5	C21—C22—H22	117.8
H12B—C12—H12C	109.5	C17—C22—H22	117.8
C5—C13—C14	115.5 (2)
N1—C1—C2—C3	0.0 (3)	C6—C5—C13—C14	−60.3 (3)
N1—C1—C2—C9	−179.8 (2)	C5—C13—C14—N3	−59.4 (3)
C1—C2—C3—C4	178.4 (2)	C5—C13—C14—C15	−172.7 (2)
C9—C2—C3—C4	−1.7 (4)	N3—C14—C15—O1	−3.8 (3)
C1—C2—C3—C8	0.3 (2)	C13—C14—C15—O1	117.2 (2)
C9—C2—C3—C8	−179.9 (2)	C7—C8—N1—C1	−178.0 (2)
C8—C3—C4—C5	1.4 (3)	C3—C8—N1—C1	0.5 (2)
C2—C3—C4—C5	−176.5 (2)	C2—C1—N1—C8	−0.3 (3)
C3—C4—C5—C6	−1.4 (3)	C9—C10—N2—C11	171.7 (2)
C3—C4—C5—C13	177.4 (2)	C9—C10—N2—C12	−67.2 (3)
C4—C5—C6—C7	0.3 (3)	O2—C16—N3—C14	−179.6 (3)
C13—C5—C6—C7	−178.6 (2)	O1—C16—N3—C14	1.2 (3)
C5—C6—C7—C8	0.8 (4)	C13—C14—N3—C16	−118.4 (2)
C6—C7—C8—N1	177.5 (2)	C15—C14—N3—C16	1.7 (3)
C6—C7—C8—C3	−0.8 (3)	O2—C16—O1—C15	176.8 (3)
C4—C3—C8—N1	−178.94 (18)	N3—C16—O1—C15	−3.9 (3)
C2—C3—C8—N1	−0.5 (2)	C14—C15—O1—C16	4.8 (3)
C4—C3—C8—C7	−0.3 (3)	C22—C17—C18—C19	0.6 (9)
C2—C3—C8—C7	178.16 (19)	C17—C18—C19—C20	−1.4 (9)
C1—C2—C9—C10	−6.7 (4)	C18—C19—C20—C21	0.2 (9)
C3—C2—C9—C10	173.5 (2)	C19—C20—C21—C22	1.7 (7)
C2—C9—C10—N2	177.3 (2)	C20—C21—C22—C17	−2.5 (8)
C4—C5—C13—C14	120.8 (2)	C18—C17—C22—C21	1.4 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2^i	0.93 (3)	1.99 (3)	2.898 (3)	165 (2)
N3—H3N···N2^ii	0.84 (3)	2.10 (3)	2.933 (3)	171 (3)
C15—H15A···O2^iii	0.97	2.58	3.269 (3)	128
C1—H1···Cg1^iv	0.93	2.88	3.768	159
C11—H11A···Cg2^v	0.96	2.83	3.658	145
C13—H13B···Cg3^vi	0.96	2.87	3.699	144

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

(II) (S)-4-{3-[2-(dimethylamino)ethyl]-1H-indol-5- ylmethyl}oxazolidin-2-one phenol solvate

Crystal data

C16H21N3O2·C6H6O	F(000) = 816
Mr = 381.47	Dx = 1.218 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.7618 (13) Å	Cell parameters from 9402 reflections
b = 19.506 (3) Å	θ = 2.6–27.7°
c = 12.1767 (18) Å	µ = 0.08 mm^−1
β = 91.399 (2)°	T = 293 K
V = 2080.5 (5) Å^3	Prism, colourless
Z = 4	0.22 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3521 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 25.0°, θmin = 1.7°
ω scans	h = −10→10
19466 measured reflections	k = −23→23
3780 independent reflections	l = −14→14

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0829P)^2 + 0.257P] where P = (Fo^2 + 2Fc^2)/3
3780 reflections	(Δ/σ)max < 0.001
530 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.17 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
C1A	0.0667 (4)	0.85185 (18)	1.0309 (3)	0.0466 (7)
H1A	−0.0063	0.8294	1.0717	0.056*
C1B	0.5595 (4)	1.01868 (18)	0.4661 (3)	0.0493 (8)
H1D	0.4831	1.0410	0.4255	0.059*
C2A	0.0615 (4)	0.92011 (17)	1.0021 (3)	0.0431 (7)
C2B	0.5549 (4)	0.95126 (17)	0.4978 (3)	0.0439 (7)
C3A	0.1966 (3)	0.93233 (16)	0.9404 (3)	0.0387 (7)
C3B	0.6963 (4)	0.93904 (16)	0.5581 (3)	0.0393 (7)
C4A	0.2546 (3)	0.99029 (16)	0.8885 (3)	0.0412 (7)
H4A	0.2040	1.0320	0.8939	0.049*
C4B	0.7561 (3)	0.88108 (16)	0.6115 (3)	0.0407 (7)
H4D	0.7028	0.8399	0.6094	0.049*
C5A	0.3881 (4)	0.98585 (18)	0.8288 (3)	0.0441 (7)
C5B	0.8956 (4)	0.88561 (17)	0.6674 (3)	0.0421 (7)
C6A	0.4642 (4)	0.9224 (2)	0.8240 (3)	0.0515 (8)
H6A	0.5529	0.9194	0.7838	0.062*
C6B	0.9761 (4)	0.94829 (19)	0.6674 (3)	0.0524 (8)
H6D	1.0700	0.9509	0.7044	0.063*
C7A	0.4129 (4)	0.86466 (18)	0.8762 (3)	0.0479 (8)
H7A	0.4664	0.8236	0.8731	0.057*
C7B	0.9201 (4)	1.00561 (18)	0.6143 (3)	0.0521 (8)
H7D	0.9750	1.0464	0.6147	0.063*
C8A	0.2763 (4)	0.86987 (16)	0.9345 (3)	0.0405 (7)
C8B	0.7783 (4)	1.00080 (17)	0.5596 (3)	0.0428 (7)
C9A	−0.0567 (4)	0.97266 (19)	1.0273 (4)	0.0547 (9)
H9A	−0.0839	0.9972	0.9604	0.066*
H9B	−0.0131	1.0055	1.0790	0.066*
C9B	0.4344 (4)	0.8987 (2)	0.4779 (4)	0.0589 (10)
H9D	0.4064	0.8793	0.5480	0.071*
H9E	0.4764	0.8620	0.4342	0.071*
C10A	−0.2002 (4)	0.94285 (17)	1.0751 (3)	0.0437 (7)
H10A	−0.2457	0.9111	1.0225	0.052*
H10B	−0.1726	0.9171	1.1408	0.052*
C10B	0.2911 (4)	0.92560 (18)	0.4199 (3)	0.0454 (7)
H10D	0.2439	0.9595	0.4664	0.054*
H10E	0.3198	0.9483	0.3526	0.054*
C11A	−0.4536 (4)	0.9613 (2)	1.1369 (4)	0.0640 (10)
H11A	−0.4315	0.9324	1.1990	0.096*
H11B	−0.4942	0.9341	1.0773	0.096*
H11C	−0.5273	0.9954	1.1567	0.096*
C11B	0.0370 (4)	0.9042 (2)	0.3530 (4)	0.0622 (10)
H11D	0.0559	0.9289	0.2864	0.093*
H11E	0.0008	0.9354	0.4075	0.093*
H11F	−0.0386	0.8695	0.3388	0.093*
C12A	−0.2576 (5)	1.0397 (2)	1.1928 (4)	0.0650 (11)
H12A	−0.2300	1.0122	1.2556	0.097*
H12B	−0.3360	1.0715	1.2121	0.097*
H12C	−0.1697	1.0644	1.1689	0.097*
C12B	0.2342 (5)	0.8254 (2)	0.3093 (3)	0.0639 (10)
H12D	0.2648	0.8512	0.2464	0.096*
H12E	0.1543	0.7941	0.2879	0.096*
H12F	0.3200	0.8001	0.3384	0.096*
C13A	0.4443 (4)	1.0485 (2)	0.7684 (3)	0.0508 (8)
H13A	0.3747	1.0861	0.7813	0.061*
H13B	0.4410	1.0388	0.6902	0.061*
C13B	0.9572 (4)	0.82348 (19)	0.7282 (3)	0.0487 (8)
H13D	0.8829	0.7868	0.7212	0.058*
H13E	0.9677	0.8348	0.8056	0.058*
C14A	0.6050 (4)	1.07125 (19)	0.8011 (3)	0.0472 (8)
H14A	0.6793	1.0360	0.7816	0.057*
C14B	1.1098 (4)	0.79737 (18)	0.6889 (3)	0.0452 (7)
H14D	1.1899	0.8311	0.7056	0.054*
C15A	0.6449 (5)	1.1397 (2)	0.7469 (3)	0.0594 (10)
H15A	0.7369	1.1353	0.7048	0.071*
H15B	0.5623	1.1547	0.6982	0.071*
C15B	1.1535 (5)	0.7272 (2)	0.7406 (3)	0.0597 (10)
H15D	1.2528	0.7297	0.7774	0.072*
H15E	1.0785	0.7132	0.7935	0.072*
C16A	0.6575 (4)	1.15411 (19)	0.9320 (3)	0.0506 (8)
C16B	1.1330 (4)	0.71385 (19)	0.5553 (3)	0.0463 (8)
N1A	0.1952 (3)	0.82185 (15)	0.9906 (2)	0.0472 (6)
N1B	0.6936 (3)	1.04863 (16)	0.5032 (3)	0.0502 (7)
N2A	−0.3146 (3)	0.99488 (15)	1.1032 (2)	0.0460 (6)
N2B	0.1789 (3)	0.87200 (15)	0.3930 (2)	0.0446 (6)
N3A	0.6217 (4)	1.08869 (16)	0.9149 (3)	0.0533 (7)
N3B	1.1100 (4)	0.78010 (16)	0.5736 (3)	0.0493 (7)
O1A	0.6677 (3)	1.18744 (14)	0.8353 (2)	0.0632 (7)
O1B	1.1564 (3)	0.68024 (13)	0.6507 (2)	0.0578 (6)
O2A	0.6812 (4)	1.18399 (15)	1.0185 (2)	0.0699 (8)
O2B	1.1336 (3)	0.68342 (14)	0.4678 (2)	0.0613 (7)
H1BN	0.729 (4)	1.088 (2)	0.495 (3)	0.045 (10)*
H3AN	0.619 (4)	1.064 (2)	0.971 (3)	0.041 (9)*
H3BN	1.116 (4)	0.805 (2)	0.523 (3)	0.049 (11)*
H5D	0.965 (4)	0.718 (6)	0.381 (7)	0.18 (4)*
C17A	0.6548 (6)	0.6835 (3)	0.5820 (5)	0.0780 (13)
C18A	0.5648 (6)	0.6927 (3)	0.6690 (6)	0.0929 (17)
H18A	0.4812	0.7219	0.6626	0.111*
C19A	0.5929 (8)	0.6608 (4)	0.7638 (6)	0.1009 (19)
H19A	0.5303	0.6693	0.8229	0.121*
C20A	0.7112 (10)	0.6161 (4)	0.7766 (6)	0.116 (3)
H20A	0.7276	0.5928	0.8424	0.140*
C21A	0.8080 (7)	0.6061 (3)	0.6877 (7)	0.0985 (18)
H21A	0.8915	0.5769	0.6952	0.118*
C22A	0.7799 (6)	0.6390 (3)	0.5906 (5)	0.0838 (16)
H22A	0.8427	0.6321	0.5311	0.101*
O3A	0.6220 (5)	0.7193 (3)	0.4878 (4)	0.1084 (13)
H3A	0.696 (7)	0.699 (4)	0.454 (6)	0.15 (3)*
H1AN	0.229 (5)	0.779 (3)	0.999 (3)	0.059 (11)*
C17B	0.8462 (6)	0.7203 (3)	0.2452 (4)	0.0779 (14)
C18B	0.9362 (6)	0.6839 (3)	0.1762 (5)	0.0828 (14)
H18D	1.0215	0.6604	0.2031	0.099*
C19B	0.8975 (11)	0.6828 (4)	0.0649 (6)	0.118 (3)
H19D	0.9560	0.6567	0.0178	0.141*
C20B	0.7751 (14)	0.7191 (5)	0.0226 (7)	0.131 (3)
H20D	0.7543	0.7213	−0.0525	0.157*
C21B	0.6877 (10)	0.7509 (5)	0.0944 (7)	0.119 (3)
H21D	0.5997	0.7724	0.0675	0.143*
C22B	0.7178 (6)	0.7543 (3)	0.2041 (6)	0.0931 (17)
H22D	0.6546	0.7787	0.2503	0.112*
O3B	0.8729 (5)	0.7252 (3)	0.3554 (3)	0.1074 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0513 (18)	0.0367 (17)	0.0520 (18)	−0.0027 (14)	0.0037 (14)	0.0036 (14)
C1B	0.0497 (18)	0.0390 (17)	0.059 (2)	0.0066 (15)	−0.0005 (15)	0.0034 (15)
C2A	0.0428 (16)	0.0351 (16)	0.0514 (18)	−0.0018 (13)	0.0031 (13)	0.0003 (14)
C2B	0.0415 (16)	0.0368 (17)	0.0531 (18)	0.0028 (14)	−0.0028 (13)	0.0032 (14)
C3A	0.0371 (14)	0.0335 (16)	0.0453 (16)	−0.0017 (12)	−0.0038 (12)	−0.0036 (12)
C3B	0.0372 (15)	0.0352 (16)	0.0455 (16)	0.0007 (12)	0.0027 (12)	−0.0046 (13)
C4A	0.0378 (15)	0.0323 (15)	0.0532 (18)	0.0008 (13)	−0.0021 (13)	−0.0035 (13)
C4B	0.0383 (15)	0.0340 (15)	0.0499 (17)	0.0018 (13)	−0.0001 (12)	−0.0040 (13)
C5A	0.0430 (16)	0.0423 (17)	0.0468 (17)	−0.0090 (14)	−0.0054 (13)	−0.0038 (14)
C5B	0.0396 (15)	0.0416 (17)	0.0451 (16)	0.0066 (13)	−0.0001 (12)	−0.0076 (13)
C6A	0.0392 (16)	0.056 (2)	0.060 (2)	−0.0018 (15)	0.0048 (14)	−0.0125 (17)
C6B	0.0402 (16)	0.0503 (19)	0.066 (2)	0.0039 (15)	−0.0094 (15)	−0.0126 (17)
C7A	0.0413 (16)	0.0401 (17)	0.062 (2)	0.0054 (14)	−0.0026 (14)	−0.0108 (15)
C7B	0.0460 (18)	0.0388 (18)	0.071 (2)	−0.0076 (14)	−0.0007 (16)	−0.0113 (16)
C8A	0.0397 (15)	0.0337 (16)	0.0477 (17)	0.0005 (12)	−0.0064 (12)	−0.0040 (13)
C8B	0.0420 (16)	0.0350 (16)	0.0515 (18)	0.0009 (13)	0.0051 (13)	−0.0048 (14)
C9A	0.0502 (19)	0.0365 (17)	0.078 (2)	0.0023 (15)	0.0132 (17)	0.0056 (17)
C9B	0.052 (2)	0.0397 (19)	0.084 (3)	−0.0022 (16)	−0.0170 (18)	0.0108 (18)
C10A	0.0408 (16)	0.0374 (16)	0.0530 (18)	0.0026 (13)	0.0027 (13)	0.0000 (14)
C10B	0.0394 (16)	0.0390 (17)	0.0575 (19)	0.0015 (14)	−0.0039 (14)	0.0024 (15)
C11A	0.0456 (19)	0.071 (3)	0.075 (3)	−0.0014 (18)	0.0088 (17)	−0.001 (2)
C11B	0.0446 (18)	0.065 (2)	0.076 (3)	0.0008 (17)	−0.0137 (17)	0.005 (2)
C12A	0.060 (2)	0.067 (3)	0.068 (2)	0.008 (2)	−0.0006 (18)	−0.022 (2)
C12B	0.065 (2)	0.067 (3)	0.060 (2)	−0.005 (2)	0.0022 (18)	−0.017 (2)
C13A	0.0451 (17)	0.056 (2)	0.0510 (18)	−0.0103 (16)	−0.0011 (14)	0.0045 (16)
C13B	0.0494 (18)	0.052 (2)	0.0443 (17)	0.0064 (16)	−0.0015 (13)	−0.0006 (15)
C14A	0.0431 (16)	0.0470 (19)	0.0518 (19)	−0.0042 (14)	0.0093 (13)	−0.0014 (15)
C14B	0.0418 (16)	0.0458 (18)	0.0476 (17)	0.0057 (14)	−0.0073 (13)	−0.0002 (14)
C15A	0.060 (2)	0.064 (2)	0.054 (2)	−0.0215 (19)	0.0047 (17)	0.0057 (18)
C15B	0.060 (2)	0.069 (3)	0.050 (2)	0.0205 (19)	−0.0041 (16)	0.0091 (18)
C16A	0.055 (2)	0.0455 (19)	0.0516 (19)	−0.0083 (16)	0.0026 (15)	−0.0003 (16)
C16B	0.0413 (17)	0.0418 (18)	0.056 (2)	0.0040 (14)	0.0044 (14)	0.0005 (16)
N1A	0.0522 (16)	0.0297 (14)	0.0595 (17)	0.0024 (12)	−0.0007 (13)	0.0026 (12)
N1B	0.0520 (16)	0.0302 (14)	0.0683 (19)	−0.0049 (13)	−0.0006 (14)	0.0017 (13)
N2A	0.0410 (14)	0.0454 (15)	0.0517 (16)	0.0038 (12)	0.0014 (11)	−0.0009 (13)
N2B	0.0417 (14)	0.0419 (14)	0.0498 (15)	−0.0011 (12)	−0.0033 (11)	−0.0004 (12)
N3A	0.0687 (19)	0.0372 (15)	0.0538 (18)	−0.0147 (14)	−0.0052 (14)	0.0060 (14)
N3B	0.0638 (18)	0.0389 (16)	0.0452 (16)	0.0130 (13)	0.0036 (13)	0.0063 (13)
O1A	0.0855 (19)	0.0425 (14)	0.0622 (15)	−0.0198 (13)	0.0116 (13)	0.0054 (12)
O1B	0.0633 (15)	0.0448 (14)	0.0650 (15)	0.0120 (12)	−0.0047 (12)	0.0089 (12)
O2A	0.100 (2)	0.0470 (15)	0.0622 (16)	−0.0200 (16)	0.0032 (14)	−0.0077 (13)
O2B	0.0745 (17)	0.0497 (14)	0.0600 (15)	0.0085 (13)	0.0062 (12)	−0.0078 (13)
C17A	0.072 (3)	0.071 (3)	0.092 (3)	−0.022 (3)	0.013 (2)	−0.017 (3)
C18A	0.072 (3)	0.094 (4)	0.114 (4)	−0.030 (3)	0.019 (3)	−0.027 (4)
C19A	0.097 (4)	0.108 (5)	0.099 (4)	−0.033 (4)	0.019 (3)	−0.024 (4)
C20A	0.138 (6)	0.110 (5)	0.100 (4)	−0.065 (5)	−0.018 (4)	0.004 (4)
C21A	0.081 (3)	0.076 (3)	0.139 (5)	−0.024 (3)	−0.001 (3)	−0.003 (4)
C22A	0.069 (3)	0.074 (3)	0.110 (4)	−0.024 (3)	0.023 (3)	−0.020 (3)
O3A	0.088 (3)	0.113 (4)	0.124 (4)	0.010 (3)	0.009 (2)	0.001 (3)
C17B	0.078 (3)	0.085 (3)	0.070 (3)	−0.027 (3)	−0.011 (2)	0.019 (3)
C18B	0.067 (3)	0.079 (3)	0.101 (4)	−0.018 (3)	−0.006 (2)	0.012 (3)
C19B	0.166 (7)	0.095 (5)	0.091 (4)	−0.051 (5)	0.006 (4)	−0.014 (4)
C20B	0.177 (8)	0.120 (6)	0.093 (5)	−0.069 (6)	−0.053 (5)	0.012 (5)
C21B	0.115 (5)	0.120 (6)	0.119 (6)	−0.051 (5)	−0.056 (4)	0.051 (5)
C22B	0.064 (3)	0.090 (4)	0.125 (5)	−0.014 (3)	−0.013 (3)	0.028 (3)
O3B	0.078 (2)	0.166 (4)	0.078 (2)	−0.006 (3)	−0.0009 (18)	0.013 (3)

Geometric parameters (Å, º)

C1A—N1A	1.370 (5)	C12B—H12D	0.9600
C1A—C2A	1.377 (5)	C12B—H12E	0.9600
C1A—H1A	0.9300	C12B—H12F	0.9600
C1B—C2B	1.371 (5)	C13A—C14A	1.520 (5)
C1B—N1B	1.379 (5)	C13A—H13A	0.9700
C1B—H1D	0.9300	C13A—H13B	0.9700
C2A—C3A	1.438 (5)	C13B—C14B	1.519 (5)
C2A—C9A	1.494 (5)	C13B—H13D	0.9700
C2B—C3B	1.445 (5)	C13B—H13E	0.9700
C2B—C9B	1.488 (5)	C14A—N3A	1.432 (5)
C3A—C4A	1.397 (5)	C14A—C15A	1.533 (5)
C3A—C8A	1.407 (4)	C14A—H14A	0.9800
C3B—C4B	1.399 (5)	C14B—N3B	1.444 (5)
C3B—C8B	1.402 (5)	C14B—C15B	1.550 (5)
C4A—C5A	1.395 (5)	C14B—H14D	0.9800
C4A—H4A	0.9300	C15A—O1A	1.434 (5)
C4B—C5B	1.388 (5)	C15A—H15A	0.9700
C4B—H4D	0.9300	C15A—H15B	0.9700
C5A—C6A	1.408 (5)	C15B—O1B	1.429 (5)
C5A—C13A	1.514 (5)	C15B—H15D	0.9700
C5B—C6B	1.412 (5)	C15B—H15E	0.9700
C5B—C13B	1.513 (5)	C16A—O2A	1.217 (5)
C6A—C7A	1.374 (5)	C16A—N3A	1.329 (5)
C6A—H6A	0.9300	C16A—O1A	1.350 (4)
C6B—C7B	1.376 (5)	C16B—O2B	1.220 (4)
C6B—H6D	0.9300	C16B—N3B	1.327 (5)
C7A—C8A	1.410 (5)	C16B—O1B	1.345 (4)
C7A—H7A	0.9300	N1A—H1AN	0.89 (5)
C7B—C8B	1.398 (5)	N1B—H1BN	0.83 (4)
C7B—H7D	0.9300	N3A—H3AN	0.84 (4)
C8A—N1A	1.368 (5)	N3B—H3BN	0.79 (4)
C8B—N1B	1.367 (5)	C17A—C18A	1.348 (8)
C9A—C10A	1.515 (5)	C17A—O3A	1.366 (7)
C9A—H9A	0.9700	C17A—C22A	1.400 (8)
C9A—H9B	0.9700	C18A—C19A	1.329 (10)
C9B—C10B	1.519 (5)	C18A—H18A	0.9300
C9B—H9D	0.9700	C19A—C20A	1.360 (11)
C9B—H9E	0.9700	C19A—H19A	0.9300
C10A—N2A	1.473 (4)	C20A—C21A	1.405 (11)
C10A—H10A	0.9700	C20A—H20A	0.9300
C10A—H10B	0.9700	C21A—C22A	1.364 (9)
C10B—N2B	1.467 (4)	C21A—H21A	0.9300
C10B—H10D	0.9700	C22A—H22A	0.9300
C10B—H10E	0.9700	O3A—H3A	0.87 (6)
C11A—N2A	1.451 (5)	C17B—O3B	1.360 (6)
C11A—H11A	0.9600	C17B—C18B	1.365 (8)
C11A—H11B	0.9600	C17B—C22B	1.389 (8)
C11A—H11C	0.9600	C18B—C19B	1.389 (9)
C11B—N2B	1.465 (5)	C18B—H18D	0.9300
C11B—H11D	0.9600	C19B—C20B	1.375 (13)
C11B—H11E	0.9600	C19B—H19D	0.9300
C11B—H11F	0.9600	C20B—C21B	1.329 (14)
C12A—N2A	1.476 (5)	C20B—H20D	0.9300
C12A—H12A	0.9600	C21B—C22B	1.357 (10)
C12A—H12B	0.9600	C21B—H21D	0.9300
C12A—H12C	0.9600	C22B—H22D	0.9300
C12B—N2B	1.458 (5)	O3B—H5D	0.87 (5)
N1A—C1A—C2A	110.2 (3)	C14A—C13A—H13A	108.6
N1A—C1A—H1A	124.9	C5A—C13A—H13B	108.6
C2A—C1A—H1A	124.9	C14A—C13A—H13B	108.6
C2B—C1B—N1B	110.2 (3)	H13A—C13A—H13B	107.5
C2B—C1B—H1D	124.9	C5B—C13B—C14B	114.9 (3)
N1B—C1B—H1D	124.9	C5B—C13B—H13D	108.6
C1A—C2A—C3A	105.7 (3)	C14B—C13B—H13D	108.6
C1A—C2A—C9A	129.1 (3)	C5B—C13B—H13E	108.6
C3A—C2A—C9A	125.3 (3)	C14B—C13B—H13E	108.6
C1B—C2B—C3B	105.7 (3)	H13D—C13B—H13E	107.5
C1B—C2B—C9B	129.9 (3)	N3A—C14A—C13A	113.3 (3)
C3B—C2B—C9B	124.4 (3)	N3A—C14A—C15A	101.0 (3)
C4A—C3A—C8A	119.4 (3)	C13A—C14A—C15A	111.2 (3)
C4A—C3A—C2A	133.2 (3)	N3A—C14A—H14A	110.3
C8A—C3A—C2A	107.4 (3)	C13A—C14A—H14A	110.3
C4B—C3B—C8B	120.2 (3)	C15A—C14A—H14A	110.3
C4B—C3B—C2B	132.5 (3)	N3B—C14B—C13B	114.0 (3)
C8B—C3B—C2B	107.3 (3)	N3B—C14B—C15B	100.5 (3)
C5A—C4A—C3A	120.3 (3)	C13B—C14B—C15B	112.2 (3)
C5A—C4A—H4A	119.8	N3B—C14B—H14D	109.9
C3A—C4A—H4A	119.8	C13B—C14B—H14D	109.9
C5B—C4B—C3B	119.5 (3)	C15B—C14B—H14D	109.9
C5B—C4B—H4D	120.3	O1A—C15A—C14A	105.8 (3)
C3B—C4B—H4D	120.3	O1A—C15A—H15A	110.6
C4A—C5A—C6A	118.7 (3)	C14A—C15A—H15A	110.6
C4A—C5A—C13A	119.4 (3)	O1A—C15A—H15B	110.6
C6A—C5A—C13A	121.9 (3)	C14A—C15A—H15B	110.6
C4B—C5B—C6B	119.3 (3)	H15A—C15A—H15B	108.7
C4B—C5B—C13B	119.2 (3)	O1B—C15B—C14B	105.3 (3)
C6B—C5B—C13B	121.5 (3)	O1B—C15B—H15D	110.7
C7A—C6A—C5A	122.7 (3)	C14B—C15B—H15D	110.7
C7A—C6A—H6A	118.6	O1B—C15B—H15E	110.7
C5A—C6A—H6A	118.6	C14B—C15B—H15E	110.7
C7B—C6B—C5B	122.1 (3)	H15D—C15B—H15E	108.8
C7B—C6B—H6D	119.0	O2A—C16A—N3A	129.1 (4)
C5B—C6B—H6D	119.0	O2A—C16A—O1A	120.7 (3)
C6A—C7A—C8A	117.7 (3)	N3A—C16A—O1A	110.2 (3)
C6A—C7A—H7A	121.1	O2B—C16B—N3B	128.6 (3)
C8A—C7A—H7A	121.1	O2B—C16B—O1B	120.9 (3)
C6B—C7B—C8B	118.2 (3)	N3B—C16B—O1B	110.5 (3)
C6B—C7B—H7D	120.9	C1A—N1A—C8A	109.1 (3)
C8B—C7B—H7D	120.9	C1A—N1A—H1AN	129 (3)
N1A—C8A—C3A	107.6 (3)	C8A—N1A—H1AN	122 (3)
N1A—C8A—C7A	131.2 (3)	C8B—N1B—C1B	108.9 (3)
C3A—C8A—C7A	121.1 (3)	C8B—N1B—H1BN	119 (3)
N1B—C8B—C7B	131.2 (3)	C1B—N1B—H1BN	132 (3)
N1B—C8B—C3B	108.0 (3)	C11A—N2A—C10A	109.6 (3)
C7B—C8B—C3B	120.8 (3)	C11A—N2A—C12A	109.2 (3)
C2A—C9A—C10A	113.7 (3)	C10A—N2A—C12A	111.1 (3)
C2A—C9A—H9A	108.8	C12B—N2B—C11B	109.2 (3)
C10A—C9A—H9A	108.8	C12B—N2B—C10B	111.6 (3)
C2A—C9A—H9B	108.8	C11B—N2B—C10B	109.1 (3)
C10A—C9A—H9B	108.8	C16A—N3A—C14A	113.5 (3)
H9A—C9A—H9B	107.7	C16A—N3A—H3AN	117 (3)
C2B—C9B—C10B	114.4 (3)	C14A—N3A—H3AN	130 (3)
C2B—C9B—H9D	108.7	C16B—N3B—C14B	113.2 (3)
C10B—C9B—H9D	108.7	C16B—N3B—H3BN	117 (3)
C2B—C9B—H9E	108.7	C14B—N3B—H3BN	128 (3)
C10B—C9B—H9E	108.7	C16A—O1A—C15A	109.3 (3)
H9D—C9B—H9E	107.6	C16B—O1B—C15B	110.1 (3)
N2A—C10A—C9A	113.6 (3)	C18A—C17A—O3A	118.5 (6)
N2A—C10A—H10A	108.8	C18A—C17A—C22A	119.7 (6)
C9A—C10A—H10A	108.8	O3A—C17A—C22A	121.8 (5)
N2A—C10A—H10B	108.8	C19A—C18A—C17A	121.4 (7)
C9A—C10A—H10B	108.8	C19A—C18A—H18A	119.3
H10A—C10A—H10B	107.7	C17A—C18A—H18A	119.3
N2B—C10B—C9B	113.5 (3)	C18A—C19A—C20A	121.6 (6)
N2B—C10B—H10D	108.9	C18A—C19A—H19A	119.2
C9B—C10B—H10D	108.9	C20A—C19A—H19A	119.2
N2B—C10B—H10E	108.9	C19A—C20A—C21A	118.3 (7)
C9B—C10B—H10E	108.9	C19A—C20A—H20A	120.8
H10D—C10B—H10E	107.7	C21A—C20A—H20A	120.8
N2A—C11A—H11A	109.5	C22A—C21A—C20A	120.2 (7)
N2A—C11A—H11B	109.5	C22A—C21A—H21A	119.9
H11A—C11A—H11B	109.5	C20A—C21A—H21A	119.9
N2A—C11A—H11C	109.5	C21A—C22A—C17A	118.8 (6)
H11A—C11A—H11C	109.5	C21A—C22A—H22A	120.6
H11B—C11A—H11C	109.5	C17A—C22A—H22A	120.6
N2B—C11B—H11D	109.5	C17A—O3A—H3A	91 (6)
N2B—C11B—H11E	109.5	O3B—C17B—C18B	123.8 (5)
H11D—C11B—H11E	109.5	O3B—C17B—C22B	116.1 (6)
N2B—C11B—H11F	109.5	C18B—C17B—C22B	120.1 (5)
H11D—C11B—H11F	109.5	C17B—C18B—C19B	118.5 (6)
H11E—C11B—H11F	109.5	C17B—C18B—H18D	120.7
N2A—C12A—H12A	109.5	C19B—C18B—H18D	120.7
N2A—C12A—H12B	109.5	C20B—C19B—C18B	121.8 (8)
H12A—C12A—H12B	109.5	C20B—C19B—H19D	119.1
N2A—C12A—H12C	109.5	C18B—C19B—H19D	119.1
H12A—C12A—H12C	109.5	C21B—C20B—C19B	116.8 (7)
H12B—C12A—H12C	109.5	C21B—C20B—H20D	121.6
N2B—C12B—H12D	109.5	C19B—C20B—H20D	121.6
N2B—C12B—H12E	109.5	C20B—C21B—C22B	124.6 (8)
H12D—C12B—H12E	109.5	C20B—C21B—H21D	117.7
N2B—C12B—H12F	109.5	C22B—C21B—H21D	117.7
H12D—C12B—H12F	109.5	C21B—C22B—C17B	117.9 (7)
H12E—C12B—H12F	109.5	C21B—C22B—H22D	121.1
C5A—C13A—C14A	114.8 (3)	C17B—C22B—H22D	121.1
C5A—C13A—H13A	108.6	C17B—O3B—H5D	118 (7)
N1A—C1A—C2A—C3A	−0.2 (4)	C5A—C13A—C14A—N3A	−60.0 (4)
N1A—C1A—C2A—C9A	179.8 (4)	C5A—C13A—C14A—C15A	−172.9 (3)
N1B—C1B—C2B—C3B	−0.2 (4)	C5B—C13B—C14B—N3B	−57.0 (4)
N1B—C1B—C2B—C9B	179.6 (4)	C5B—C13B—C14B—C15B	−170.5 (3)
C1A—C2A—C3A—C4A	179.2 (3)	N3A—C14A—C15A—O1A	−4.0 (4)
C9A—C2A—C3A—C4A	−0.8 (6)	C13A—C14A—C15A—O1A	116.5 (3)
C1A—C2A—C3A—C8A	0.5 (4)	N3B—C14B—C15B—O1B	−5.7 (4)
C9A—C2A—C3A—C8A	−179.5 (3)	C13B—C14B—C15B—O1B	115.8 (3)
C1B—C2B—C3B—C4B	179.0 (4)	C2A—C1A—N1A—C8A	−0.1 (4)
C9B—C2B—C3B—C4B	−0.7 (6)	C3A—C8A—N1A—C1A	0.4 (4)
C1B—C2B—C3B—C8B	0.2 (4)	C7A—C8A—N1A—C1A	−178.2 (3)
C9B—C2B—C3B—C8B	−179.5 (3)	C7B—C8B—N1B—C1B	−178.7 (4)
C8A—C3A—C4A—C5A	1.8 (5)	C3B—C8B—N1B—C1B	0.1 (4)
C2A—C3A—C4A—C5A	−176.8 (3)	C2B—C1B—N1B—C8B	0.0 (4)
C8B—C3B—C4B—C5B	1.2 (5)	C9A—C10A—N2A—C11A	173.9 (3)
C2B—C3B—C4B—C5B	−177.5 (3)	C9A—C10A—N2A—C12A	−65.3 (4)
C3A—C4A—C5A—C6A	−1.3 (5)	C9B—C10B—N2B—C12B	−67.8 (4)
C3A—C4A—C5A—C13A	176.9 (3)	C9B—C10B—N2B—C11B	171.5 (3)
C3B—C4B—C5B—C6B	−1.4 (5)	O2A—C16A—N3A—C14A	−178.8 (4)
C3B—C4B—C5B—C13B	177.9 (3)	O1A—C16A—N3A—C14A	0.4 (5)
C4A—C5A—C6A—C7A	−0.4 (5)	C13A—C14A—N3A—C16A	−116.6 (4)
C13A—C5A—C6A—C7A	−178.5 (3)	C15A—C14A—N3A—C16A	2.4 (4)
C4B—C5B—C6B—C7B	0.6 (5)	O2B—C16B—N3B—C14B	177.0 (3)
C13B—C5B—C6B—C7B	−178.7 (3)	O1B—C16B—N3B—C14B	−2.5 (4)
C5A—C6A—C7A—C8A	1.5 (5)	C13B—C14B—N3B—C16B	−115.2 (3)
C5B—C6B—C7B—C8B	0.4 (5)	C15B—C14B—N3B—C16B	5.1 (4)
C4A—C3A—C8A—N1A	−179.5 (3)	O2A—C16A—O1A—C15A	176.1 (4)
C2A—C3A—C8A—N1A	−0.6 (4)	N3A—C16A—O1A—C15A	−3.2 (4)
C4A—C3A—C8A—C7A	−0.7 (5)	C14A—C15A—O1A—C16A	4.6 (4)
C2A—C3A—C8A—C7A	178.2 (3)	O2B—C16B—O1B—C15B	178.7 (3)
C6A—C7A—C8A—N1A	177.5 (3)	N3B—C16B—O1B—C15B	−1.7 (4)
C6A—C7A—C8A—C3A	−1.0 (5)	C14B—C15B—O1B—C16B	4.8 (4)
C6B—C7B—C8B—N1B	178.2 (4)	O3A—C17A—C18A—C19A	−178.2 (5)
C6B—C7B—C8B—C3B	−0.6 (5)	C22A—C17A—C18A—C19A	0.7 (8)
C4B—C3B—C8B—N1B	−179.2 (3)	C17A—C18A—C19A—C20A	−1.8 (9)
C2B—C3B—C8B—N1B	−0.2 (4)	C18A—C19A—C20A—C21A	2.4 (9)
C4B—C3B—C8B—C7B	−0.2 (5)	C19A—C20A—C21A—C22A	−2.0 (9)
C2B—C3B—C8B—C7B	178.8 (3)	C20A—C21A—C22A—C17A	0.9 (8)
C1A—C2A—C9A—C10A	−10.7 (6)	C18A—C17A—C22A—C21A	−0.3 (7)
C3A—C2A—C9A—C10A	169.3 (3)	O3A—C17A—C22A—C21A	178.6 (5)
C1B—C2B—C9B—C10B	−4.2 (6)	O3B—C17B—C18B—C19B	−179.9 (5)
C3B—C2B—C9B—C10B	175.5 (3)	C22B—C17B—C18B—C19B	1.0 (8)
C2A—C9A—C10A—N2A	178.2 (3)	C17B—C18B—C19B—C20B	2.3 (9)
C2B—C9B—C10B—N2B	175.3 (3)	C18B—C19B—C20B—C21B	−5.3 (11)
C4A—C5A—C13A—C14A	122.3 (4)	C19B—C20B—C21B—C22B	5.4 (12)
C6A—C5A—C13A—C14A	−59.6 (5)	C20B—C21B—C22B—C17B	−2.2 (10)
C4B—C5B—C13B—C14B	119.6 (3)	O3B—C17B—C22B—C21B	179.7 (5)
C6B—C5B—C13B—C14B	−61.2 (4)	C18B—C17B—C22B—C21B	−1.1 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1BN···O2B^i	0.83 (4)	2.26 (4)	3.050 (4)	159 (4)
N3A—H3AN···N2A^ii	0.84 (4)	2.17 (4)	2.975 (4)	162 (3)
N3B—H3BN···N2B^ii	0.79 (4)	2.14 (5)	2.912 (4)	169 (4)
N1A—H1AN···O2A^iii	0.89 (5)	2.02 (5)	2.902 (4)	166 (4)
C15A—H15A···O2B^i	0.97	2.59	3.403 (5)	142
O3A—H3A···O3B	0.87 (6)	2.05 (7)	2.760 (6)	137 (9)
O3B—H5D···O2B	0.87 (5)	1.92 (4)	2.758 (5)	162 (10)
C1A—H1A···Cg1^iv	0.93	2.81	3.683	156
C1B—H1D···Cg2^v	0.93	2.86	3.747	160
C11A—H11C···Cg3^ii	0.96	2.80	3.648	148
C11B—H11F···Cg3^ii	0.96	2.92	3.733	143
C13B—H13D···Cg4^vi	0.97	2.81	3.666	148

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