Pseudomerohedral twinning, pseudosymmetry and complex hydrogen-bonded sheets in 2-meth­oxy-4-(pyrrolo­[1,2-a]quinoxalin-4-yl)phenol

The title compound, C₁₈H₁₄N₂O₂, crystallizes as a nonmero­hedral twin, but the structure can be satisfactorily refined as a merohedral twin, in which a monoclinic unit cell with a cell angle [beta] close to 90° emulates a metrically ortho­rhom­bic cell. The two mol­ecules in the asymmetric unit are very similar in structure and they are related by an approximate pseudo-screw axis. The mol­ecules are linked into complex sheets by a combination of two O-H...N hydrogen bonds and four C-H...O hydrogen bonds.

S1. Comment

Pyrrolo[1,2-a]quinoxaline constitutes a privileged heterocyclic system because of its potential bioactivity; some compounds containing this system have shown antiproliferative activity against human leukaemia and breast cancer (Desplat et al., 2010) and antileishmanial activity (Guillon et al., 2007). They also show promise as anti-ulcer agents because they are potential bacterial multidrug resistance pump inhibitors (Vidaillac Guillon, Arpin et al., 2007; Vidaillac Guillon, Moreau et al., 2007). Here, we report the molecular and supramolecular structure of the title compound, (I), which was prepared by simple cyclocondensation of 1-(2-aminophenyl)pyrrole with an aromatic aldehyde catalysed with L-proline.

Compound (I) (Fig. 1) crystallizes with Z' = 2 in the centrosymmetric space group P2₁/c, with a unit cell having the cell angle β = 90.326 (12)°, i.e. fairly close to 90°. Although analysis of the reflection data indicated that (I) had crystallized as a non-merohedral twin, the form of the twinning matrix showed that the twinning was close to merohedral, emulating a metrically orthorhombic cell. In fact, it proved possible to refine the structure either as a non-merohedral twin using a modified reflection file, or as a merohedral twin using an unmodifed reflection file, and we report both refinements here, denoted (Inm) and (Im) for the non-merohedral and merohedral twin models, respectively. As the atomic coordinates and geometric parameters derived from them are extremely similar for the two refinements, we discuss here only the results of the refinement as a non-merohedral twin.

The bond lengths and angles in the two independent molecules are very similar (Table 1), and the conformations of the two molecules in the selected asymmetric unit, as indicated by the key torsion angles (Table 1), are almost identical, but a search for possible additional crystallographic symmetry revealed none. However, the coordinates of pairs of corresponding atoms in the two molecules of the selected asymmetric unit are approximately related by the transformation (1/2 + x, 1/2 - y, 1.36 - z), corresponding to an approximate, but non-crystallographic, pseudo-screw axis along the line (x, 1/4, 0.68) (Fig. 2).

Within the fused tricyclic component of the molecules, the bond distances (Table 1) indicate some interesting patterns. In the five-membered rings, the C—C distances span ranges of less than 0.04 Å, even though Cx2—Cx3 (x = 1 or 2) are formally single bonds, while Cx1—Cx2 and Cx3—Cx3a are formally double bonds, thus indicating a degree of 6π electron delocalization in these rings. In the carbocyclic rings, the bond distances support aromatic delocalization, but with some slight bond fixation in the Cx6—Cx7 and Cx8—Cx9 bonds, while in the central rings there are clearly localized double bonds at the Cx4—Nx5 bonds. Overall, therefore, the pattern of two 6π circuits in the two outer rings of the fused system, with a localized double bond in the central ring, is reminiscent of the electronic structure of phenanthrene and related molecules (Glidewell & Lloyd, 1984, 1986).

Just three torsion angles (Table 1) suffice to define the molecular conformation. In each molecule, atom Cx47 (x = 1 or 2) of the methoxy group is almost coplanar with the adjacent ring, with deviations from the mean planes of 0.102 (3) and 0.063 (3) Å for atoms C147 and C247, respectively. Accordingly, the exocyclic C—C—O angles at each atom Cx45 show the usual difference of ca 10° (Seip & Seip, 1973; Ferguson et al., 1996). The pendent aryl rings make dihedral angles with the adjacent heterocyclic rings of 33.8 (2) and 35.7 (2)° in the type 1 and 2 molecules (for which n x? = 1 or 2, respectively), and even the H—O—C—C torsion angles are very similar in the two molecules. These conformations mean that the molecules have no internal symmetry, and hence that they are chiral, but the centrosymmetric space group accommodates equal numbers of the two conformational enantiomers for each type of molecule.

The supramolecular structure of (I) is built using two O—H···N hydrogen bonds and four C—H···O hydrogen bonds, which utilize all four of the O atoms present in the asymmetric unit (Table 2). The resulting sheet formation can be readily analysed in terms of two one-dimensional substructures (Ferguson et al., 1998a,b; Gregson et al., 2000). Just as atom O144 acts as hydrogen-bond donor to atom N25 within the selected asymmetric unit, so also atom O244 at (x, y, z) acts as hydrogen-bond donor to atom N15 at (1 + x, y, z), so forming a C²₂(16) chain (Bernstein et al., 1995) running parallel to the [100] direction. The formation of the one-dimensional substructure along [100] is augmented by two of the C—H···O hydrogen bonds. Atom C26 acts as hydrogen-bond donor to the hydroxyl atom O144 within the selected asymmetric unit, and atom C16 at (x, y, z) acts as donor to the hydroxyl atom O244 at (-1 + x, y, z), so that these two hydrogen bonds form a C²₂(20) chain, also parallel to [100] but antiparallel to the C²₂(16) motif. The combination of all four of these hydrogen bonds generates a C²₂(16)C²₂(20)[R²₂(6)][R²₂(6)] chain of rings along [100] (Fig. 3).

Two further C—H···O hydrogen bonds generate a second one-dimensional substructure in the form of a chain of edge-fused rings, itself built from two independent simple chain motifs. Atom C11 in the type 1 molecule at (x, y, z) acts as hydrogen-bond donor to the methoxy atom O145 at (x, 1/2 - y, 1/2 + z), so forming C(9) chain built from type 1 molecules related by the c-glide plane at y = 1/4, and thus running parallel to the [001] direction. In a similar way, atom C21 in the type 2 molecule at (x, y, z) acts as hydrogen-bond donor to the methoxy atom O245 at (x, 1/2 - y, -1/2 + z), so forming a second C(9) chain along [001], this time containing only type 2 molecules and running antiparallel to the chain containing type 1 molecules. These two chains are linked by the O—H···N hydrogen bond within the asymmetric unit to form a ribbon, or a chain of edge-fused R⁴₄(28) rings running parallel to [001] (Fig. 4). The combination of the two chains of rings along [100] and [001] produces a complex sheet lying parallel to (010).

Related literature

For related literature, see: Bernstein et al. (1995); Desplat et al. (2010); Ferguson et al. (1996, 1998a, 1998b); Glidewell & Lloyd (1984, 1986); Gregson et al. (2000); Guillon et al. (2007); Seip & Seip (1973); Spek (2009); Vidaillac, Guillon, Arpin, Forfar-Bares, Ba, Grellet, Moreau, Caignard, Jarry & Quentin (2007); Vidaillac, Guillon, Moreau, Arpin, Lagardere, Larrouture, Dallemagne, Caignard, Quentin & Jarry (2007).

S2. Experimental

A mixture of 1-(2-aminophenyl)pyrrole (1 mmol), 4-hydroxy-3-methoxybenzaldehyde (1 mmol), L-proline (20% w/w with respect to the pyrrole), Pd/C (50% w/w with respect to the pyrrole) and acetonitrile (2 ml) was stirred at ambient temperature for 48 h. The progress of the reaction was monitored by thin-layer chromatography, and when the reaction was thus judged to be complete the Pd/C was removed by filtration and the solvent was removed under reduced pressure. The resulting solid product, (I), was purified by column chromatography on silica gel using dichloromethane as the eluent. Yellow crystals of (I) suitable for single-crystal X-ray diffraction were grown by slow evaporation, at ambient temperature and in air, of a solution in ethanol (83% yield, m.p. 414 K). MS (70 eV) m/z (%) 290 (100) [M+], 275 (8), 261 (9); elemental analysis, found: C 74.4, H 5.0, N 9.6%; C₁₈H₁₄N₂O₂ requires: C 74.5, H 4.86, N 9.7%.

S3. Refinement

The initial refinement converged to a high R index of 0.103, and analysis of the fcf data indicated that the refinement should be handled as a non-merohedral twin, with twinning matrix (-1.000, 0.000, -0.004/0.000, -1.000, 0.000/0.000, 0.000, 1.000). From the original HKLF file (38684 measured reflections, of which 6234 were unique with a merging index of 0.0661), a modified file was prepared by use of the TwinRotMat option in PLATON (Spek, 2009) for use in the final refinement as a non-merohedral twin, to give twin fractions of 0.1234 (13) and 0.8766 (13).

All H atoms were located in difference maps. H atoms bonded to C atoms were then treated as riding in geometrically idealized positions, with C—H = 0.95 (all ring atoms) or 0.98 Å (methyl), and with U_iso(H) = kU_eq(C), where k = 1.5 for the methyl groups, which were permitted to rotatae but not to tilt, and 1.2 for all other H atoms bonded to C atoms. H atoms bonded to atoms O144 and O244 were permitted to ride at the positions deduced from difference maps, with U_iso(H) = 1.5U_eq(O), giving O—H distances of 0.98 and 0.95 Å, respectively.

The form of the twinning matrix suggested that the twinning was pseudo-merohedral, as the twinning matrix approximated to (-1, 0, 0/0, -1, 0/0, 0, 1), corresponding to a monoclinic cell having the cell angle β close to 90°, emulating a metrically orthorhombic cell. Accordingly, the structure was also refined as a merohedral twin, to give twin fractions of 0.1228 (13) and 0.8772 (13). The H atoms were handled exactly as for the non-merohedral twin, now giving O—H distances of 0.97 and 0.96 Å, respectively. For refinements conducted under otherwise identical conditions, the merohedral twin actually gave a slightly smaller R factor, but the atomic coordinates and derived intramolecular geometric parameters from the two refinements are virtually indistinguishable, apart from the O—H distances.

Computing details

For both compounds, data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures

	Fig. 1. The independent molecular components of (I), showing the atom-labelling scheme. (a) Molecule 1, containing atom N15. (b) Molecule 2, containing atom N25. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A stereoview of the selected asymmetric unit of (I), showing the pseudo-symmetric relationship of the two independent molecules. For the sake of clarity, all H atoms have been omitted.
	Fig. 3. A stereoview of part of the crystal structure of (I), showing the formation of a chain of rings parallel to [100] and built from two O—H···N hydrogen bonds and two C—H···O hydrogen bonds. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
	Fig. 4. A stereoview of part of the crystal structure of (I), showing the formation of a chain of edge-fused rings parallel to [001] and built from one O—H···N hydrogen bond and two C—H···O hydrogen bonds. For the sake of clarity, H atoms bonded to C atoms but not involved in the motifs shown have been omitted.

(Inm) 2-methoxy-4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenol

Crystal data

C18H14N2O2	F(000) = 1216
Mr = 290.31	Dx = 1.419 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6234 reflections
a = 7.9278 (8) Å	θ = 2.8–27.5°
b = 15.2929 (18) Å	µ = 0.09 mm^−1
c = 22.410 (4) Å	T = 120 K
β = 90.326 (12)°	Block, colourless
V = 2717.0 (6) Å^3	0.50 × 0.26 × 0.18 mm
Z = 8

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	5057 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	3891 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Detector resolution: 9.091 pixels mm^-1	θmax = 25.5°, θmin = 2.8°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −18→18
Tmin = 0.944, Tmax = 0.983	l = 0→27
5057 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0805P)^2 + 2.4154P] where P = (Fo^2 + 2Fc^2)/3
5057 reflections	(Δ/σ)max = 0.001
400 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

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

	x	y	z	Uiso*/Ueq
C11	0.0184 (4)	0.1510 (2)	0.98347 (13)	0.0310 (7)
H11	0.0047	0.1599	1.0251	0.037*
C12	0.1091 (4)	0.0857 (2)	0.95767 (14)	0.0333 (7)
H12	0.1693	0.0410	0.9781	0.040*
C13	0.0983 (4)	0.09596 (19)	0.89577 (13)	0.0278 (6)
H13	0.1509	0.0600	0.8667	0.033*
C13a	−0.0023 (3)	0.16762 (18)	0.88456 (12)	0.0228 (6)
C14	−0.0612 (4)	0.21193 (18)	0.83257 (12)	0.0216 (6)
N15	−0.1579 (3)	0.28065 (15)	0.83561 (10)	0.0232 (5)
C15a	−0.2001 (3)	0.31409 (19)	0.89120 (12)	0.0228 (6)
C16	−0.2951 (4)	0.39025 (19)	0.89378 (13)	0.0257 (6)
H16	−0.3318	0.4177	0.8580	0.031*
C17	−0.3363 (4)	0.4260 (2)	0.94796 (13)	0.0294 (7)
H17	−0.4017	0.4780	0.9496	0.035*
C18	−0.2827 (4)	0.3862 (2)	1.00025 (14)	0.0313 (7)
H18	−0.3116	0.4112	1.0376	0.038*
C19	−0.1890 (4)	0.31159 (19)	0.99881 (13)	0.0280 (7)
H19	−0.1531	0.2846	1.0349	0.034*
C19a	−0.1463 (4)	0.27535 (18)	0.94433 (12)	0.0232 (6)
N19b	−0.0488 (3)	0.20078 (15)	0.93964 (10)	0.0235 (5)
C141	−0.0072 (4)	0.18395 (18)	0.77312 (12)	0.0227 (6)
C142	0.0205 (4)	0.09758 (18)	0.75782 (12)	0.0249 (6)
H142	0.0005	0.0527	0.7862	0.030*
C143	0.0768 (4)	0.07622 (19)	0.70171 (13)	0.0271 (6)
H143	0.0979	0.0167	0.6921	0.033*
C144	0.1030 (4)	0.13962 (19)	0.65934 (12)	0.0251 (6)
C145	0.0707 (4)	0.22617 (18)	0.67364 (12)	0.0226 (6)
C146	0.0187 (3)	0.24808 (18)	0.73002 (12)	0.0229 (6)
H146	0.0001	0.3078	0.7398	0.027*
O144	0.1571 (3)	0.11436 (13)	0.60516 (9)	0.0321 (5)
H144	0.2139	0.1592	0.5815	0.048*
O145	0.0958 (3)	0.28506 (12)	0.62874 (8)	0.0276 (5)
C147	0.0839 (4)	0.37452 (19)	0.64402 (13)	0.0321 (7)
H17A	−0.0307	0.3874	0.6576	0.048*
H17B	0.1095	0.4104	0.6090	0.048*
H17C	0.1646	0.3878	0.6760	0.048*
C21	0.5093 (4)	0.33346 (18)	0.37435 (13)	0.0257 (6)
H21	0.4974	0.3249	0.3326	0.031*
C22	0.6028 (4)	0.39751 (19)	0.40166 (13)	0.0273 (6)
H22	0.6666	0.4413	0.3819	0.033*
C23	0.5886 (4)	0.38756 (18)	0.46330 (13)	0.0253 (6)
H23	0.6414	0.4228	0.4929	0.030*
C23a	0.4840 (3)	0.31729 (18)	0.47326 (12)	0.0212 (6)
C24	0.4249 (3)	0.27254 (17)	0.52452 (12)	0.0211 (6)
N25	0.3264 (3)	0.20487 (15)	0.52100 (10)	0.0220 (5)
C25a	0.2837 (3)	0.17208 (18)	0.46495 (12)	0.0213 (6)
C26	0.1858 (4)	0.09683 (19)	0.46108 (12)	0.0247 (6)
H26	0.1459	0.0701	0.4966	0.030*
C27	0.1459 (4)	0.06052 (19)	0.40699 (13)	0.0266 (6)
H27	0.0791	0.0090	0.4051	0.032*
C28	0.2035 (4)	0.09935 (19)	0.35495 (13)	0.0277 (7)
H28	0.1766	0.0739	0.3174	0.033*
C29	0.2984 (4)	0.17361 (19)	0.35726 (12)	0.0252 (6)
H29	0.3370	0.2001	0.3215	0.030*
C29a	0.3381 (3)	0.21024 (18)	0.41211 (12)	0.0214 (6)
N29b	0.4369 (3)	0.28457 (15)	0.41763 (10)	0.0224 (5)
C241	0.4828 (4)	0.29995 (18)	0.58448 (12)	0.0230 (6)
C242	0.5091 (4)	0.38573 (18)	0.59991 (12)	0.0249 (6)
H242	0.4867	0.4305	0.5716	0.030*
C243	0.5676 (4)	0.40775 (19)	0.65597 (13)	0.0263 (6)
H243	0.5851	0.4675	0.6657	0.032*
C244	0.6009 (4)	0.34452 (19)	0.69814 (12)	0.0262 (6)
C245	0.5693 (3)	0.25756 (18)	0.68371 (12)	0.0234 (6)
C246	0.5126 (3)	0.23562 (18)	0.62765 (12)	0.0225 (6)
H246	0.4933	0.1759	0.6181	0.027*
O244	0.6599 (3)	0.36976 (13)	0.75195 (9)	0.0332 (5)
H244	0.7113	0.3226	0.7724	0.050*
O245	0.5984 (3)	0.19940 (13)	0.72875 (8)	0.0286 (5)
C247	0.5849 (4)	0.10910 (19)	0.71431 (14)	0.0337 (7)
H27A	0.6643	0.0949	0.6824	0.051*
H27B	0.4696	0.0962	0.7009	0.051*
H27C	0.6114	0.0739	0.7497	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0341 (16)	0.0384 (18)	0.0206 (15)	−0.0071 (14)	−0.0061 (12)	0.0052 (13)
C12	0.0339 (17)	0.0343 (17)	0.0315 (17)	−0.0040 (14)	−0.0087 (13)	0.0090 (14)
C13	0.0257 (15)	0.0287 (15)	0.0290 (16)	−0.0036 (13)	−0.0028 (12)	0.0016 (13)
C13a	0.0219 (14)	0.0262 (15)	0.0202 (14)	−0.0061 (12)	0.0014 (11)	−0.0003 (11)
C14	0.0238 (14)	0.0219 (14)	0.0193 (14)	−0.0049 (12)	−0.0009 (11)	−0.0017 (11)
N15	0.0273 (12)	0.0246 (13)	0.0178 (12)	−0.0056 (11)	0.0003 (9)	−0.0026 (10)
C15a	0.0234 (14)	0.0256 (15)	0.0194 (14)	−0.0072 (12)	0.0012 (11)	−0.0036 (12)
C16	0.0275 (15)	0.0267 (15)	0.0229 (14)	−0.0062 (12)	0.0003 (11)	−0.0011 (12)
C17	0.0308 (16)	0.0272 (16)	0.0303 (16)	−0.0061 (13)	0.0053 (12)	−0.0062 (13)
C18	0.0375 (17)	0.0314 (17)	0.0250 (15)	−0.0113 (14)	0.0051 (13)	−0.0074 (13)
C19	0.0323 (16)	0.0324 (16)	0.0192 (14)	−0.0120 (14)	0.0009 (12)	−0.0023 (12)
C19a	0.0256 (14)	0.0245 (15)	0.0194 (14)	−0.0085 (12)	0.0001 (11)	−0.0016 (11)
N19b	0.0272 (13)	0.0259 (13)	0.0175 (12)	−0.0056 (10)	−0.0016 (9)	0.0012 (10)
C141	0.0250 (14)	0.0251 (15)	0.0181 (14)	−0.0010 (12)	−0.0007 (11)	0.0004 (11)
C142	0.0304 (15)	0.0230 (14)	0.0215 (14)	−0.0037 (12)	0.0032 (11)	0.0010 (12)
C143	0.0328 (16)	0.0213 (14)	0.0273 (15)	−0.0013 (13)	0.0032 (12)	−0.0026 (12)
C144	0.0292 (15)	0.0273 (15)	0.0189 (14)	−0.0023 (13)	0.0024 (11)	−0.0035 (12)
C145	0.0265 (14)	0.0224 (14)	0.0190 (14)	−0.0021 (12)	0.0015 (11)	0.0027 (11)
C146	0.0256 (14)	0.0231 (14)	0.0200 (14)	0.0004 (12)	0.0003 (11)	−0.0024 (11)
O144	0.0467 (13)	0.0272 (11)	0.0227 (11)	−0.0038 (10)	0.0102 (9)	−0.0042 (9)
O145	0.0410 (12)	0.0215 (10)	0.0204 (10)	−0.0009 (9)	0.0031 (9)	0.0008 (8)
C147	0.0480 (19)	0.0223 (15)	0.0260 (16)	−0.0029 (14)	0.0053 (13)	0.0004 (12)
C21	0.0312 (16)	0.0245 (15)	0.0214 (14)	0.0064 (13)	0.0041 (12)	0.0056 (12)
C22	0.0282 (15)	0.0253 (15)	0.0286 (15)	0.0024 (12)	0.0047 (12)	0.0044 (12)
C23	0.0271 (15)	0.0226 (15)	0.0261 (15)	0.0044 (12)	0.0008 (11)	−0.0008 (12)
C23a	0.0229 (14)	0.0228 (14)	0.0179 (13)	0.0053 (12)	−0.0005 (11)	−0.0010 (11)
C24	0.0248 (14)	0.0216 (14)	0.0170 (13)	0.0041 (12)	−0.0009 (10)	0.0002 (11)
N25	0.0233 (12)	0.0241 (12)	0.0185 (12)	0.0028 (10)	−0.0011 (9)	−0.0016 (10)
C25a	0.0220 (14)	0.0221 (14)	0.0197 (14)	0.0065 (11)	−0.0021 (11)	−0.0001 (11)
C26	0.0280 (15)	0.0249 (15)	0.0212 (14)	0.0046 (12)	0.0006 (11)	0.0006 (12)
C27	0.0278 (15)	0.0240 (15)	0.0279 (15)	0.0035 (13)	−0.0053 (12)	−0.0036 (12)
C28	0.0334 (16)	0.0287 (16)	0.0210 (15)	0.0065 (13)	−0.0056 (12)	−0.0059 (12)
C29	0.0301 (16)	0.0279 (15)	0.0177 (14)	0.0064 (13)	−0.0018 (11)	0.0005 (12)
C29a	0.0228 (14)	0.0223 (14)	0.0192 (14)	0.0049 (12)	−0.0019 (11)	0.0005 (11)
N29b	0.0254 (12)	0.0235 (12)	0.0184 (12)	0.0036 (10)	0.0008 (9)	0.0010 (10)
C241	0.0251 (14)	0.0254 (15)	0.0185 (14)	0.0008 (12)	0.0001 (11)	−0.0001 (11)
C242	0.0299 (15)	0.0221 (14)	0.0226 (14)	0.0018 (12)	−0.0013 (12)	0.0020 (12)
C243	0.0328 (16)	0.0208 (14)	0.0252 (15)	0.0037 (12)	−0.0037 (12)	−0.0031 (12)
C244	0.0290 (15)	0.0289 (16)	0.0206 (14)	0.0021 (12)	−0.0039 (11)	−0.0039 (12)
C245	0.0259 (14)	0.0237 (15)	0.0206 (14)	0.0010 (12)	−0.0014 (11)	0.0020 (11)
C246	0.0263 (14)	0.0204 (14)	0.0208 (14)	0.0007 (12)	−0.0006 (11)	−0.0018 (11)
O244	0.0500 (13)	0.0280 (11)	0.0214 (11)	0.0048 (10)	−0.0128 (9)	−0.0047 (9)
O245	0.0416 (12)	0.0247 (10)	0.0194 (10)	−0.0001 (9)	−0.0056 (9)	0.0031 (8)
C247	0.0502 (19)	0.0260 (16)	0.0248 (16)	0.0004 (15)	−0.0069 (14)	0.0032 (13)

Geometric parameters (Å, º)

C11—C12	1.361 (5)	C21—C22	1.370 (4)
C12—C13	1.398 (4)	C22—C23	1.395 (4)
C13—C13a	1.378 (4)	C23—C23a	1.376 (4)
C13a—C14	1.424 (4)	C23a—C24	1.419 (4)
C14—N15	1.303 (4)	C24—N25	1.299 (4)
N15—C15a	1.389 (4)	N25—C25a	1.393 (3)
C15a—C16	1.389 (4)	C25a—C26	1.391 (4)
C16—C17	1.373 (4)	C26—C27	1.369 (4)
C17—C18	1.385 (4)	C27—C28	1.388 (4)
C18—C19	1.361 (4)	C28—C29	1.363 (4)
C19—C19a	1.384 (4)	C29—C29a	1.385 (4)
C19a—N19b	1.382 (4)	C29a—N29b	1.386 (4)
N19b—C11	1.350 (4)	N29b—C21	1.355 (4)
C13a—N19b	1.386 (4)	C23a—N29b	1.393 (3)
C15a—C19a	1.395 (4)	C25a—C29a	1.391 (4)
C11—H11	0.9500	C21—H21	0.9500
C12—H12	0.9500	C22—H22	0.9500
C13—H13	0.9500	C23—H23	0.9500
C14—C141	1.466 (4)	C24—C241	1.478 (4)
C16—H16	0.9500	C26—H26	0.9500
C17—H17	0.9500	C27—H27	0.9500
C18—H18	0.9500	C28—H28	0.9500
C19—H19	0.9500	C29—H29	0.9500
C141—C142	1.383 (4)	C241—C242	1.372 (4)
C141—C146	1.392 (4)	C241—C246	1.399 (4)
C142—C143	1.376 (4)	C242—C243	1.378 (4)
C142—H142	0.9500	C242—H242	0.9500
C143—C144	1.374 (4)	C243—C244	1.377 (4)
C143—H143	0.9500	C243—H243	0.9500
C144—O144	1.347 (3)	C244—O244	1.347 (3)
C144—C145	1.386 (4)	C244—C245	1.391 (4)
C145—O145	1.366 (3)	C245—O245	1.364 (3)
C145—C146	1.373 (4)	C245—C246	1.374 (4)
C146—H146	0.9500	C246—H246	0.9500
O144—H144	0.9788	O244—H244	0.9457
O145—C147	1.414 (3)	O245—C247	1.422 (3)
C147—H17A	0.9800	C247—H27A	0.9800
C147—H17B	0.9800	C247—H27B	0.9800
C147—H17C	0.9800	C247—H27C	0.9800
N19b—C11—C12	108.2 (3)	N29b—C21—C22	107.8 (3)
N19b—C11—H11	125.9	N29b—C21—H21	126.1
C12—C11—H11	125.9	C22—C21—H21	126.1
C11—C12—C13	108.0 (3)	C21—C22—C23	108.5 (3)
C11—C12—H12	126.0	C21—C22—H22	125.7
C13—C12—H12	126.0	C23—C22—H22	125.7
C13a—C13—C12	107.6 (3)	C23a—C23—C22	107.3 (3)
C13a—C13—H13	126.2	C23a—C23—H23	126.3
C12—C13—H13	126.2	C22—C23—H23	126.3
C13—C13a—N19b	106.6 (2)	C23—C23a—N29b	107.1 (2)
C13—C13a—C14	135.6 (3)	C23—C23a—C24	135.2 (3)
N19b—C13a—C14	117.8 (2)	N29b—C23a—C24	117.6 (2)
N15—C14—C13a	122.1 (2)	N25—C24—C23a	122.4 (2)
N15—C14—C141	117.3 (2)	N25—C24—C241	117.7 (2)
C13a—C14—C141	120.6 (2)	C23a—C24—C241	119.8 (2)
C14—N15—C15a	119.2 (2)	C24—N25—C25a	119.0 (2)
C16—C15a—N15	118.7 (3)	C26—C25a—C29a	118.0 (2)
C16—C15a—C19a	119.0 (3)	C26—C25a—N25	119.2 (2)
N15—C15a—C19a	122.4 (3)	C29a—C25a—N25	122.8 (3)
C17—C16—C15a	120.2 (3)	C27—C26—C25a	121.1 (3)
C17—C16—H16	119.9	C27—C26—H26	119.4
C15a—C16—H16	119.9	C25a—C26—H26	119.4
C16—C17—C18	120.0 (3)	C26—C27—C28	119.7 (3)
C16—C17—H17	120.0	C26—C27—H27	120.2
C18—C17—H17	120.0	C28—C27—H27	120.2
C19—C18—C17	120.9 (3)	C29—C28—C27	120.6 (3)
C19—C18—H18	119.6	C29—C28—H28	119.7
C17—C18—H18	119.6	C27—C28—H28	119.7
C18—C19—C19a	119.5 (3)	C28—C29—C29a	119.6 (3)
C18—C19—H19	120.3	C28—C29—H29	120.2
C19a—C19—H19	120.3	C29a—C29—H29	120.2
N19b—C19a—C19	122.5 (3)	C29—C29a—N29b	122.5 (2)
N19b—C19a—C15a	117.0 (2)	C29—C29a—C25a	121.0 (3)
C19—C19a—C15a	120.5 (3)	N29b—C29a—C25a	116.5 (2)
C11—N19b—C19a	129.0 (2)	C21—N29b—C29a	129.1 (2)
C11—N19b—C13a	109.6 (2)	C21—N29b—C23a	109.3 (2)
C19a—N19b—C13a	121.4 (2)	C29a—N29b—C23a	121.6 (2)
C142—C141—C146	118.5 (3)	C242—C241—C246	118.2 (3)
C142—C141—C14	123.5 (2)	C242—C241—C24	123.1 (2)
C146—C141—C14	118.0 (2)	C246—C241—C24	118.7 (2)
C143—C142—C141	120.4 (3)	C241—C242—C243	120.9 (3)
C143—C142—H142	119.8	C241—C242—H242	119.6
C141—C142—H142	119.8	C243—C242—H242	119.6
C144—C143—C142	121.0 (3)	C244—C243—C242	121.1 (3)
C144—C143—H143	119.5	C244—C243—H243	119.5
C142—C143—H143	119.5	C242—C243—H243	119.5
O144—C144—C143	118.1 (3)	O244—C244—C243	118.5 (3)
O144—C144—C145	122.9 (3)	O244—C244—C245	122.9 (3)
C143—C144—C145	119.0 (3)	C243—C244—C245	118.6 (3)
O145—C145—C144	115.6 (2)	O245—C245—C244	115.0 (2)
O145—C145—C146	124.3 (3)	O245—C245—C246	124.8 (3)
C146—C145—C144	120.2 (3)	C246—C245—C244	120.2 (3)
C145—C146—C141	120.8 (3)	C245—C246—C241	120.9 (3)
C145—C146—H146	119.6	C245—C246—H246	119.5
C141—C146—H146	119.6	C241—C246—H246	119.5
C144—O144—H144	115.9	C244—O244—H244	111.2
C145—O145—C147	116.7 (2)	C245—O245—C247	116.9 (2)
O145—C147—H17A	109.5	O245—C247—H27A	109.5
O145—C147—H17B	109.5	O245—C247—H27B	109.5
H17A—C147—H17B	109.5	H27A—C247—H27B	109.5
O145—C147—H17C	109.5	O245—C247—H27C	109.5
H17A—C147—H17C	109.5	H27A—C247—H27C	109.5
H17B—C147—H17C	109.5	H27B—C247—H27C	109.5
N19b—C11—C12—C13	0.4 (3)	N29b—C21—C22—C23	0.4 (3)
C11—C12—C13—C13a	−0.9 (4)	C21—C22—C23—C23a	−0.6 (3)
C12—C13—C13a—N19b	1.0 (3)	C22—C23—C23a—N29b	0.6 (3)
C12—C13—C13a—C14	179.8 (3)	C22—C23—C23a—C24	177.5 (3)
C13—C13a—C14—N15	−179.7 (3)	C23—C23a—C24—N25	−178.6 (3)
N19b—C13a—C14—N15	−1.1 (4)	N29b—C23a—C24—N25	−1.9 (4)
C13—C13a—C14—C141	−2.9 (5)	C23—C23a—C24—C241	−1.8 (5)
N19b—C13a—C14—C141	175.7 (2)	N29b—C23a—C24—C241	174.8 (2)
C13a—C14—N15—C15a	2.5 (4)	C23a—C24—N25—C25a	3.3 (4)
C141—C14—N15—C15a	−174.4 (2)	C241—C24—N25—C25a	−173.5 (2)
C14—N15—C15a—C16	176.3 (3)	C24—N25—C25a—C26	176.5 (2)
C14—N15—C15a—C19a	−1.8 (4)	C24—N25—C25a—C29a	−1.9 (4)
N15—C15a—C16—C17	−178.8 (3)	C29a—C25a—C26—C27	0.9 (4)
C19a—C15a—C16—C17	−0.6 (4)	N25—C25a—C26—C27	−177.6 (2)
C15a—C16—C17—C18	0.2 (4)	C25a—C26—C27—C28	−0.1 (4)
C16—C17—C18—C19	0.0 (5)	C26—C27—C28—C29	−0.5 (4)
C17—C18—C19—C19a	0.3 (4)	C27—C28—C29—C29a	0.3 (4)
C18—C19—C19a—N19b	178.7 (3)	C28—C29—C29a—N29b	178.6 (3)
C18—C19—C19a—C15a	−0.7 (4)	C28—C29—C29a—C25a	0.4 (4)
C16—C15a—C19a—N19b	−178.6 (2)	C26—C25a—C29a—C29	−1.0 (4)
N15—C15a—C19a—N19b	−0.5 (4)	N25—C25a—C29a—C29	177.4 (3)
C16—C15a—C19a—C19	0.9 (4)	C26—C25a—C29a—N29b	−179.3 (2)
N15—C15a—C19a—C19	178.9 (3)	N25—C25a—C29a—N29b	−0.9 (4)
C12—C11—N19b—C19a	−178.1 (3)	C22—C21—N29b—C29a	−176.6 (3)
C12—C11—N19b—C13a	0.3 (3)	C22—C21—N29b—C23a	0.0 (3)
C19—C19a—N19b—C11	0.8 (4)	C29—C29a—N29b—C21	0.2 (4)
C15a—C19a—N19b—C11	−179.8 (3)	C25a—C29a—N29b—C21	178.5 (3)
C19—C19a—N19b—C13a	−177.5 (3)	C29—C29a—N29b—C23a	−176.0 (2)
C15a—C19a—N19b—C13a	1.9 (4)	C25a—C29a—N29b—C23a	2.3 (4)
C13—C13a—N19b—C11	−0.8 (3)	C23—C23a—N29b—C21	−0.4 (3)
C14—C13a—N19b—C11	−179.8 (2)	C24—C23a—N29b—C21	−177.9 (2)
C13—C13a—N19b—C19a	177.8 (2)	C23—C23a—N29b—C29a	176.5 (2)
C14—C13a—N19b—C19a	−1.3 (4)	C24—C23a—N29b—C29a	−1.0 (4)
N15—C14—C141—C142	−147.5 (3)	N25—C24—C241—C242	−145.8 (3)
C13a—C14—C141—C142	35.5 (4)	C23a—C24—C241—C242	37.3 (4)
N15—C14—C141—C146	33.0 (4)	N25—C24—C241—C246	34.2 (4)
C13a—C14—C141—C146	−144.0 (3)	C23a—C24—C241—C246	−142.7 (3)
C146—C141—C142—C143	1.8 (4)	C246—C241—C242—C243	1.7 (4)
C14—C141—C142—C143	−177.7 (3)	C24—C241—C242—C243	−178.2 (3)
C141—C142—C143—C144	−1.5 (4)	C241—C242—C243—C244	−0.2 (4)
C142—C143—C144—O144	−179.6 (3)	C242—C243—C244—O244	179.2 (3)
C142—C143—C144—C145	−0.5 (4)	C242—C243—C244—C245	−2.0 (4)
O144—C144—C145—O145	0.6 (4)	O244—C244—C245—O245	1.6 (4)
C143—C144—C145—O145	−178.4 (3)	C243—C244—C245—O245	−177.2 (3)
O144—C144—C145—C146	−178.8 (3)	O244—C244—C245—C246	−178.6 (3)
C143—C144—C145—C146	2.1 (4)	C243—C244—C245—C246	2.6 (4)
O145—C145—C146—C141	178.8 (3)	O245—C245—C246—C241	178.6 (3)
C144—C145—C146—C141	−1.9 (4)	C244—C245—C246—C241	−1.1 (4)
C142—C141—C146—C145	−0.1 (4)	C242—C241—C246—C245	−1.1 (4)
C14—C141—C146—C145	179.4 (3)	C24—C241—C246—C245	178.9 (3)
C146—C145—O145—C147	6.9 (4)	C246—C245—O245—C247	6.6 (4)
C144—C145—O145—C147	−172.5 (3)	C244—C245—O245—C247	−173.6 (3)
C143—C144—O144—H144	−158	C243—C244—O244—H244	−161

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O144—H144···N25	0.98	1.77	2.703 (3)	158
O244—H244···N15^i	0.95	1.86	2.725 (3)	150
C11—H11···O145^ii	0.95	2.57	3.451 (4)	154
C16—H16···O244^iii	0.95	2.49	3.212 (4)	133
C21—H21···O245^iv	0.95	2.49	3.380 (3)	156
C26—H26···O144	0.95	2.53	3.249 (3)	133

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

(Im) 2-methoxy-4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenol

Crystal data

C18H14N2O2	F(000) = 1216
Mr = 290.31	Dx = 1.419 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6234 reflections
a = 7.9278 (8) Å	θ = 2.8–27.5°
b = 15.2929 (18) Å	µ = 0.09 mm^−1
c = 22.410 (4) Å	T = 120 K
β = 90.326 (12)°	Block, colourless
V = 2717.0 (6) Å^3	0.50 × 0.26 × 0.18 mm
Z = 8

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	5057 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	3891 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
Detector resolution: 9.091 pixels mm^-1	θmax = 25.5°, θmin = 2.8°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −18→18
Tmin = 0.944, Tmax = 0.983	l = 0→27
34020 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0848P)^2 + 1.9308P] where P = (Fo^2 + 2Fc^2)/3
5057 reflections	(Δ/σ)max = 0.001
400 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

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

	x	y	z	Uiso*/Ueq
C11	0.0182 (4)	0.1510 (2)	0.98350 (13)	0.0320 (7)
H11	0.0046	0.1600	1.0251	0.038*
C12	0.1090 (4)	0.0857 (2)	0.95769 (14)	0.0342 (7)
H12	0.1691	0.0410	0.9782	0.041*
C13	0.0982 (4)	0.09598 (19)	0.89576 (13)	0.0284 (6)
H13	0.1506	0.0601	0.8667	0.034*
C13a	−0.0022 (3)	0.16758 (18)	0.88460 (12)	0.0237 (6)
C14	−0.0613 (3)	0.21190 (17)	0.83260 (12)	0.0225 (6)
N15	−0.1579 (3)	0.28065 (15)	0.83559 (10)	0.0240 (5)
C15a	−0.2002 (3)	0.31405 (18)	0.89118 (12)	0.0236 (6)
C16	−0.2950 (3)	0.39022 (18)	0.89386 (13)	0.0265 (6)
H16	−0.3314	0.4177	0.8580	0.032*
C17	−0.3364 (4)	0.4259 (2)	0.94784 (13)	0.0304 (7)
H17	−0.4019	0.4779	0.9494	0.037*
C18	−0.2826 (4)	0.38614 (19)	1.00016 (14)	0.0323 (7)
H18	−0.3115	0.4112	1.0375	0.039*
C19	−0.1891 (4)	0.31159 (19)	0.99873 (13)	0.0291 (7)
H19	−0.1534	0.2846	1.0348	0.035*
C19a	−0.1463 (3)	0.27533 (18)	0.94430 (12)	0.0240 (6)
N19b	−0.0490 (3)	0.20076 (15)	0.93965 (10)	0.0245 (5)
C141	−0.0071 (4)	0.18397 (18)	0.77310 (12)	0.0235 (6)
C142	0.0204 (4)	0.09758 (18)	0.75788 (12)	0.0256 (6)
H142	0.0003	0.0527	0.7863	0.031*
C143	0.0768 (4)	0.07625 (18)	0.70172 (13)	0.0279 (6)
H143	0.0979	0.0168	0.6921	0.033*
C144	0.1029 (4)	0.13958 (18)	0.65942 (12)	0.0260 (6)
C145	0.0709 (4)	0.22617 (18)	0.67366 (12)	0.0232 (6)
C146	0.0186 (3)	0.24809 (18)	0.73001 (12)	0.0238 (6)
H146	−0.0004	0.3077	0.7397	0.029*
O144	0.1571 (3)	0.11433 (13)	0.60516 (9)	0.0329 (5)
H144	0.2117	0.1609	0.5830	0.049*
O145	0.0958 (3)	0.28506 (12)	0.62873 (8)	0.0285 (5)
C147	0.0839 (4)	0.37452 (18)	0.64407 (13)	0.0326 (7)
H17A	−0.0309	0.3875	0.6574	0.049*
H17B	0.1103	0.4104	0.6091	0.049*
H17C	0.1641	0.3876	0.6763	0.049*
C21	0.5093 (4)	0.33347 (18)	0.37436 (13)	0.0264 (6)
H21	0.4974	0.3249	0.3326	0.032*
C22	0.6026 (4)	0.39754 (19)	0.40163 (13)	0.0282 (6)
H22	0.6663	0.4414	0.3819	0.034*
C23	0.5885 (4)	0.38756 (18)	0.46328 (13)	0.0263 (6)
H23	0.6412	0.4228	0.4929	0.032*
C23a	0.4841 (3)	0.31729 (17)	0.47324 (12)	0.0222 (6)
C24	0.4247 (3)	0.27257 (17)	0.52456 (12)	0.0219 (6)
N25	0.3263 (3)	0.20487 (14)	0.52096 (10)	0.0226 (5)
C25a	0.2835 (3)	0.17209 (17)	0.46490 (12)	0.0217 (6)
C26	0.1856 (4)	0.09680 (18)	0.46109 (12)	0.0254 (6)
H26	0.1457	0.0701	0.4966	0.030*
C27	0.1458 (4)	0.06053 (19)	0.40696 (13)	0.0273 (6)
H27	0.0790	0.0090	0.4050	0.033*
C28	0.2035 (4)	0.09933 (18)	0.35494 (13)	0.0287 (7)
H28	0.1768	0.0739	0.3174	0.034*
C29	0.2983 (4)	0.17358 (19)	0.35722 (12)	0.0263 (6)
H29	0.3367	0.2001	0.3214	0.032*
C29a	0.3381 (3)	0.21022 (17)	0.41211 (12)	0.0224 (6)
N29b	0.4368 (3)	0.28456 (14)	0.41760 (10)	0.0231 (5)
C241	0.4829 (4)	0.29992 (18)	0.58450 (12)	0.0239 (6)
C242	0.5092 (4)	0.38576 (18)	0.59990 (12)	0.0258 (6)
H242	0.4868	0.4306	0.5716	0.031*
C243	0.5675 (4)	0.40771 (18)	0.65602 (12)	0.0271 (6)
H243	0.5851	0.4675	0.6657	0.032*
C244	0.6008 (4)	0.34455 (19)	0.69816 (12)	0.0270 (6)
C245	0.5694 (3)	0.25754 (18)	0.68374 (12)	0.0243 (6)
C246	0.5125 (3)	0.23561 (18)	0.62766 (12)	0.0232 (6)
H246	0.4930	0.1759	0.6181	0.028*
O244	0.6599 (3)	0.36974 (13)	0.75190 (9)	0.0338 (5)
H244	0.7112	0.3220	0.7735	0.051*
O245	0.5984 (3)	0.19940 (12)	0.72875 (8)	0.0295 (5)
C247	0.5848 (4)	0.10911 (18)	0.71435 (13)	0.0347 (7)
H27A	0.6636	0.0950	0.6822	0.052*
H27B	0.4693	0.0962	0.7012	0.052*
H27C	0.6120	0.0740	0.7497	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0357 (16)	0.0378 (18)	0.0225 (15)	−0.0068 (14)	−0.0055 (12)	0.0050 (13)
C12	0.0355 (17)	0.0340 (17)	0.0331 (17)	−0.0042 (14)	−0.0079 (13)	0.0097 (14)
C13	0.0268 (15)	0.0288 (15)	0.0296 (16)	−0.0036 (12)	−0.0020 (12)	0.0013 (13)
C13a	0.0233 (14)	0.0258 (14)	0.0219 (14)	−0.0061 (12)	0.0014 (11)	−0.0005 (11)
C14	0.0250 (14)	0.0216 (14)	0.0210 (14)	−0.0046 (12)	−0.0008 (11)	−0.0013 (11)
N15	0.0280 (12)	0.0249 (12)	0.0191 (12)	−0.0053 (10)	0.0005 (9)	−0.0024 (9)
C15a	0.0245 (14)	0.0255 (14)	0.0209 (14)	−0.0068 (12)	0.0016 (11)	−0.0038 (11)
C16	0.0288 (15)	0.0269 (15)	0.0239 (14)	−0.0059 (12)	−0.0002 (11)	−0.0013 (12)
C17	0.0325 (16)	0.0269 (16)	0.0319 (16)	−0.0057 (13)	0.0053 (12)	−0.0063 (13)
C18	0.0392 (17)	0.0314 (16)	0.0263 (16)	−0.0117 (14)	0.0057 (13)	−0.0077 (13)
C19	0.0343 (16)	0.0320 (16)	0.0211 (15)	−0.0119 (13)	0.0009 (12)	−0.0019 (12)
C19a	0.0270 (14)	0.0245 (15)	0.0207 (14)	−0.0084 (12)	0.0002 (11)	−0.0012 (11)
N19b	0.0286 (13)	0.0256 (12)	0.0192 (12)	−0.0055 (10)	−0.0015 (9)	0.0014 (10)
C141	0.0258 (14)	0.0252 (14)	0.0195 (14)	−0.0007 (12)	−0.0008 (11)	0.0000 (11)
C142	0.0314 (15)	0.0231 (14)	0.0225 (14)	−0.0032 (12)	0.0035 (11)	0.0007 (12)
C143	0.0337 (16)	0.0213 (14)	0.0286 (15)	−0.0010 (12)	0.0017 (12)	−0.0029 (12)
C144	0.0305 (15)	0.0269 (15)	0.0206 (14)	−0.0022 (12)	0.0013 (11)	−0.0037 (12)
C145	0.0273 (14)	0.0226 (14)	0.0197 (14)	−0.0020 (12)	0.0005 (11)	0.0025 (11)
C146	0.0266 (14)	0.0231 (14)	0.0216 (14)	0.0005 (12)	−0.0007 (11)	−0.0025 (11)
O144	0.0483 (13)	0.0271 (11)	0.0235 (11)	−0.0035 (10)	0.0094 (9)	−0.0044 (9)
O145	0.0423 (12)	0.0214 (10)	0.0218 (10)	−0.0007 (9)	0.0025 (9)	0.0007 (8)
C147	0.0484 (19)	0.0225 (15)	0.0270 (16)	−0.0028 (14)	0.0046 (14)	0.0003 (12)
C21	0.0322 (15)	0.0243 (14)	0.0228 (15)	0.0062 (12)	0.0045 (12)	0.0059 (12)
C22	0.0296 (15)	0.0252 (15)	0.0297 (15)	0.0025 (12)	0.0039 (12)	0.0044 (12)
C23	0.0287 (15)	0.0224 (14)	0.0278 (15)	0.0045 (12)	0.0005 (12)	−0.0007 (12)
C23a	0.0243 (14)	0.0226 (14)	0.0197 (14)	0.0054 (11)	−0.0004 (11)	−0.0012 (11)
C24	0.0258 (14)	0.0217 (14)	0.0183 (13)	0.0037 (12)	−0.0014 (11)	0.0003 (11)
N25	0.0238 (12)	0.0246 (12)	0.0194 (12)	0.0029 (10)	−0.0007 (9)	−0.0015 (9)
C25a	0.0225 (14)	0.0225 (14)	0.0203 (14)	0.0061 (11)	−0.0020 (11)	−0.0002 (11)
C26	0.0285 (15)	0.0250 (15)	0.0226 (14)	0.0045 (12)	0.0009 (11)	0.0008 (12)
C27	0.0290 (15)	0.0241 (14)	0.0288 (15)	0.0033 (12)	−0.0054 (12)	−0.0035 (12)
C28	0.0350 (16)	0.0287 (16)	0.0224 (15)	0.0065 (13)	−0.0067 (12)	−0.0056 (12)
C29	0.0314 (16)	0.0278 (15)	0.0198 (14)	0.0061 (13)	−0.0016 (11)	0.0006 (12)
C29a	0.0236 (14)	0.0221 (14)	0.0213 (14)	0.0046 (11)	−0.0012 (11)	0.0006 (11)
N29b	0.0265 (12)	0.0238 (12)	0.0190 (12)	0.0032 (10)	0.0001 (9)	0.0012 (9)
C241	0.0262 (14)	0.0253 (14)	0.0202 (14)	0.0005 (12)	0.0004 (11)	−0.0002 (11)
C242	0.0318 (15)	0.0221 (14)	0.0234 (14)	0.0016 (12)	−0.0015 (12)	0.0019 (11)
C243	0.0345 (16)	0.0207 (14)	0.0260 (15)	0.0036 (12)	−0.0038 (12)	−0.0030 (12)
C244	0.0298 (15)	0.0289 (15)	0.0220 (14)	0.0016 (12)	−0.0038 (12)	−0.0043 (12)
C245	0.0273 (14)	0.0233 (14)	0.0222 (14)	0.0008 (12)	−0.0008 (11)	0.0017 (11)
C246	0.0272 (14)	0.0205 (13)	0.0219 (14)	0.0004 (12)	−0.0008 (11)	−0.0018 (11)
O244	0.0512 (13)	0.0284 (11)	0.0217 (10)	0.0044 (10)	−0.0125 (9)	−0.0049 (9)
O245	0.0431 (12)	0.0247 (10)	0.0205 (10)	−0.0003 (9)	−0.0052 (9)	0.0031 (8)
C247	0.0517 (19)	0.0259 (16)	0.0264 (16)	0.0001 (15)	−0.0069 (14)	0.0030 (13)

Geometric parameters (Å, º)

C11—N19b	1.350 (4)	C21—N29b	1.354 (4)
C11—C12	1.362 (5)	C21—C22	1.370 (4)
C11—H11	0.9500	C21—H21	0.9500
C12—C13	1.399 (4)	C22—C23	1.395 (4)
C12—H12	0.9500	C22—H22	0.9500
C13—C13a	1.376 (4)	C23—C23a	1.376 (4)
C13—H13	0.9500	C23—H23	0.9500
C13a—N19b	1.387 (4)	C23a—N29b	1.393 (3)
C13a—C14	1.425 (4)	C23a—C24	1.421 (4)
C14—N15	1.303 (4)	C24—N25	1.298 (3)
C14—C141	1.467 (4)	C24—C241	1.478 (4)
N15—C15a	1.389 (3)	N25—C25a	1.393 (3)
C15a—C16	1.388 (4)	C25a—C29a	1.390 (4)
C15a—C19a	1.394 (4)	C25a—C26	1.391 (4)
C16—C17	1.369 (4)	C26—C27	1.369 (4)
C16—H16	0.9500	C26—H26	0.9500
C17—C18	1.386 (4)	C27—C28	1.388 (4)
C17—H17	0.9500	C27—H27	0.9500
C18—C19	1.361 (4)	C28—C29	1.362 (4)
C18—H18	0.9500	C28—H28	0.9500
C19—C19a	1.384 (4)	C29—C29a	1.387 (4)
C19—H19	0.9500	C29—H29	0.9500
C19a—N19b	1.381 (4)	C29a—N29b	1.385 (4)
C141—C142	1.382 (4)	C241—C242	1.373 (4)
C141—C146	1.392 (4)	C241—C246	1.398 (4)
C142—C143	1.377 (4)	C242—C243	1.379 (4)
C142—H142	0.9500	C242—H242	0.9500
C143—C144	1.372 (4)	C243—C244	1.375 (4)
C143—H143	0.9500	C243—H243	0.9500
C144—O144	1.349 (3)	C244—O244	1.346 (3)
C144—C145	1.386 (4)	C244—C245	1.391 (4)
C145—O145	1.366 (3)	C245—O245	1.363 (3)
C145—C146	1.373 (4)	C245—C246	1.375 (4)
C146—H146	0.9500	C246—H246	0.9500
O144—H144	0.9711	O244—H244	0.9649
O145—C147	1.414 (3)	O245—C247	1.422 (3)
C147—H17A	0.9800	C247—H27A	0.9800
C147—H17B	0.9800	C247—H27B	0.9800
C147—H17C	0.9800	C247—H27C	0.9800
N19b—C11—C12	108.2 (3)	N29b—C21—C22	107.8 (3)
N19b—C11—H11	125.9	N29b—C21—H21	126.1
C12—C11—H11	125.9	C22—C21—H21	126.1
C11—C12—C13	108.0 (3)	C21—C22—C23	108.5 (3)
C11—C12—H12	126.0	C21—C22—H22	125.8
C13—C12—H12	126.0	C23—C22—H22	125.8
C13a—C13—C12	107.6 (3)	C23a—C23—C22	107.3 (3)
C13a—C13—H13	126.2	C23a—C23—H23	126.3
C12—C13—H13	126.2	C22—C23—H23	126.3
C13—C13a—N19b	106.7 (2)	C23—C23a—N29b	107.1 (2)
C13—C13a—C14	135.6 (3)	C23—C23a—C24	135.2 (3)
N19b—C13a—C14	117.7 (2)	N29b—C23a—C24	117.6 (2)
N15—C14—C13a	122.2 (2)	N25—C24—C23a	122.4 (2)
N15—C14—C141	117.2 (2)	N25—C24—C241	117.8 (2)
C13a—C14—C141	120.5 (2)	C23a—C24—C241	119.8 (2)
C14—N15—C15a	119.2 (2)	C24—N25—C25a	119.1 (2)
C16—C15a—N15	118.7 (3)	C29a—C25a—C26	118.1 (2)
C16—C15a—C19a	118.9 (3)	C29a—C25a—N25	122.8 (2)
N15—C15a—C19a	122.4 (3)	C26—C25a—N25	119.1 (2)
C17—C16—C15a	120.4 (3)	C27—C26—C25a	121.0 (3)
C17—C16—H16	119.8	C27—C26—H26	119.5
C15a—C16—H16	119.8	C25a—C26—H26	119.5
C16—C17—C18	119.9 (3)	C26—C27—C28	119.7 (3)
C16—C17—H17	120.1	C26—C27—H27	120.1
C18—C17—H17	120.1	C28—C27—H27	120.1
C19—C18—C17	120.9 (3)	C29—C28—C27	120.6 (3)
C19—C18—H18	119.6	C29—C28—H28	119.7
C17—C18—H18	119.6	C27—C28—H28	119.7
C18—C19—C19a	119.5 (3)	C28—C29—C29a	119.5 (3)
C18—C19—H19	120.2	C28—C29—H29	120.2
C19a—C19—H19	120.2	C29a—C29—H29	120.2
N19b—C19a—C19	122.5 (3)	N29b—C29a—C29	122.4 (2)
N19b—C19a—C15a	117.1 (2)	N29b—C29a—C25a	116.6 (2)
C19—C19a—C15a	120.5 (3)	C29—C29a—C25a	121.0 (3)
C11—N19b—C19a	129.0 (2)	C21—N29b—C29a	129.1 (2)
C11—N19b—C13a	109.5 (2)	C21—N29b—C23a	109.2 (2)
C19a—N19b—C13a	121.5 (2)	C29a—N29b—C23a	121.5 (2)
C142—C141—C146	118.6 (2)	C242—C241—C246	118.3 (3)
C142—C141—C14	123.4 (2)	C242—C241—C24	123.0 (2)
C146—C141—C14	118.0 (2)	C246—C241—C24	118.7 (2)
C143—C142—C141	120.3 (3)	C241—C242—C243	120.8 (3)
C143—C142—H142	119.9	C241—C242—H242	119.6
C141—C142—H142	119.9	C243—C242—H242	119.6
C144—C143—C142	121.0 (3)	C244—C243—C242	121.2 (3)
C144—C143—H143	119.5	C244—C243—H243	119.4
C142—C143—H143	119.5	C242—C243—H243	119.4
O144—C144—C143	118.1 (3)	O244—C244—C243	118.5 (3)
O144—C144—C145	122.7 (2)	O244—C244—C245	122.8 (3)
C143—C144—C145	119.2 (3)	C243—C244—C245	118.6 (3)
O145—C145—C146	124.2 (2)	O245—C245—C246	124.8 (2)
O145—C145—C144	115.7 (2)	O245—C245—C244	115.0 (2)
C146—C145—C144	120.1 (3)	C246—C245—C244	120.2 (3)
C145—C146—C141	120.8 (3)	C245—C246—C241	120.9 (3)
C145—C146—H146	119.6	C245—C246—H246	119.5
C141—C146—H146	119.6	C241—C246—H246	119.5
C144—O144—H144	113.4	C244—O244—H244	112.1
C145—O145—C147	116.7 (2)	C245—O245—C247	117.0 (2)
O145—C147—H17A	109.5	O245—C247—H27A	109.5
O145—C147—H17B	109.5	O245—C247—H27B	109.5
H17A—C147—H17B	109.5	H27A—C247—H27B	109.5
O145—C147—H17C	109.5	O245—C247—H27C	109.5
H17A—C147—H17C	109.5	H27A—C247—H27C	109.5
H17B—C147—H17C	109.5	H27B—C247—H27C	109.5
N19b—C11—C12—C13	0.4 (3)	N29b—C21—C22—C23	0.4 (3)
C11—C12—C13—C13a	−0.8 (3)	C21—C22—C23—C23a	−0.6 (3)
C12—C13—C13a—N19b	0.9 (3)	C22—C23—C23a—N29b	0.6 (3)
C12—C13—C13a—C14	179.9 (3)	C22—C23—C23a—C24	177.6 (3)
C13—C13a—C14—N15	−179.8 (3)	C23—C23a—C24—N25	−178.6 (3)
N19b—C13a—C14—N15	−0.9 (4)	N29b—C23a—C24—N25	−1.7 (4)
C13—C13a—C14—C141	−3.1 (5)	C23—C23a—C24—C241	−2.1 (5)
N19b—C13a—C14—C141	175.7 (2)	N29b—C23a—C24—C241	174.7 (2)
C13a—C14—N15—C15a	2.4 (4)	C23a—C24—N25—C25a	3.1 (4)
C141—C14—N15—C15a	−174.4 (2)	C241—C24—N25—C25a	−173.4 (2)
C14—N15—C15a—C16	176.3 (2)	C24—N25—C25a—C29a	−1.8 (4)
C14—N15—C15a—C19a	−1.6 (4)	C24—N25—C25a—C26	176.6 (2)
N15—C15a—C16—C17	−178.8 (3)	C29a—C25a—C26—C27	0.9 (4)
C19a—C15a—C16—C17	−0.8 (4)	N25—C25a—C26—C27	−177.6 (2)
C15a—C16—C17—C18	0.4 (4)	C25a—C26—C27—C28	−0.1 (4)
C16—C17—C18—C19	−0.1 (4)	C26—C27—C28—C29	−0.5 (4)
C17—C18—C19—C19a	0.4 (4)	C27—C28—C29—C29a	0.5 (4)
C18—C19—C19a—N19b	178.7 (3)	C28—C29—C29a—N29b	178.6 (2)
C18—C19—C19a—C15a	−0.8 (4)	C28—C29—C29a—C25a	0.3 (4)
C16—C15a—C19a—N19b	−178.6 (2)	C26—C25a—C29a—N29b	−179.4 (2)
N15—C15a—C19a—N19b	−0.6 (4)	N25—C25a—C29a—N29b	−1.0 (4)
C16—C15a—C19a—C19	1.0 (4)	C26—C25a—C29a—C29	−1.0 (4)
N15—C15a—C19a—C19	179.0 (3)	N25—C25a—C29a—C29	177.4 (2)
C12—C11—N19b—C19a	−178.1 (3)	C22—C21—N29b—C29a	−176.6 (3)
C12—C11—N19b—C13a	0.2 (3)	C22—C21—N29b—C23a	−0.1 (3)
C19—C19a—N19b—C11	0.6 (4)	C29—C29a—N29b—C21	0.1 (4)
C15a—C19a—N19b—C11	−179.8 (3)	C25a—C29a—N29b—C21	178.5 (3)
C19—C19a—N19b—C13a	−177.4 (3)	C29—C29a—N29b—C23a	−176.0 (2)
C15a—C19a—N19b—C13a	2.2 (4)	C25a—C29a—N29b—C23a	2.4 (4)
C13—C13a—N19b—C11	−0.7 (3)	C23—C23a—N29b—C21	−0.3 (3)
C14—C13a—N19b—C11	−179.9 (2)	C24—C23a—N29b—C21	−178.0 (2)
C13—C13a—N19b—C19a	177.7 (2)	C23—C23a—N29b—C29a	176.5 (2)
C14—C13a—N19b—C19a	−1.5 (4)	C24—C23a—N29b—C29a	−1.2 (4)
N15—C14—C141—C142	−147.5 (3)	N25—C24—C241—C242	−145.9 (3)
C13a—C14—C141—C142	35.7 (4)	C23a—C24—C241—C242	37.5 (4)
N15—C14—C141—C146	32.8 (4)	N25—C24—C241—C246	34.0 (4)
C13a—C14—C141—C146	−144.0 (3)	C23a—C24—C241—C246	−142.6 (3)
C146—C141—C142—C143	1.9 (4)	C246—C241—C242—C243	1.7 (4)
C14—C141—C142—C143	−177.8 (3)	C24—C241—C242—C243	−178.4 (3)
C141—C142—C143—C144	−1.6 (4)	C241—C242—C243—C244	−0.1 (4)
C142—C143—C144—O144	−179.6 (3)	C242—C243—C244—O244	179.1 (3)
C142—C143—C144—C145	−0.3 (4)	C242—C243—C244—C245	−2.0 (4)
O144—C144—C145—O145	0.8 (4)	O244—C244—C245—O245	1.8 (4)
C143—C144—C145—O145	−178.4 (3)	C243—C244—C245—O245	−177.1 (3)
O144—C144—C145—C146	−178.9 (3)	O244—C244—C245—C246	−178.6 (3)
C143—C144—C145—C146	1.9 (4)	C243—C244—C245—C246	2.5 (4)
O145—C145—C146—C141	178.8 (3)	O245—C245—C246—C241	178.7 (3)
C144—C145—C146—C141	−1.6 (4)	C244—C245—C246—C241	−0.9 (4)
C142—C141—C146—C145	−0.3 (4)	C242—C241—C246—C245	−1.2 (4)
C14—C141—C146—C145	179.4 (3)	C24—C241—C246—C245	178.9 (3)
C146—C145—O145—C147	7.1 (4)	C246—C245—O245—C247	6.7 (4)
C144—C145—O145—C147	−172.6 (2)	C244—C245—O245—C247	−173.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O144—H144···N25	0.97	1.80	2.703 (3)	154
O244—H244···N15^i	0.96	1.84	2.726 (3)	151
C11—H11···O145^ii	0.95	2.57	3.450 (4)	154
C16—H16···O244^iii	0.95	2.49	3.215 (4)	133
C21—H21···O245^iv	0.95	2.49	3.380 (3)	156
C26—H26···O144	0.95	2.53	3.249 (3)	133

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