2-(7,8-Diphenyl-1H-imidazo[4,5-f]quinoxalin-2-yl)phenol methanol disolvate.

The title compound, C(27)H(18)N(4)O·2CH(4)O, is a unsymmetrically substituted quinoxaline. An intra-molecular O-H⋯N hydrogen bond involving the hydr-oxy and imino groups generates an S(6) ring motif. Inter-molecular C-H⋯O and N-H⋯O hydrogen bonds form an R(2) (1)(7) ring motif involving a methanol O atom and two H atoms of the imidazole and benzene rings, respectively. The latter links neighbouring mol-ecules into one-dimensional extended chains along the a axis. The two benzene rings are inclined towards each other, as indicated by the dihedral angle of 52.13 (10)°. The phenol ring is almost coplanar with the basic quinoxaline unit, making a dihedral angle of 2.43 (6)°. The short distances between the centroids of the five- and six-membered rings prove the existence of π-π inter-actions [centroid-centroid distances = 3.5234 (9)-3.7885 (10) Å]. The crystal structure is stabilized by intra-molecular O-H⋯N, inter-molecular O-H⋯O, N-H⋯O and C-H⋯O (× 2) hydrogen bonds and weak inter-molecular C-H⋯π and π-π inter-actions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For information about imidazolyl quinoxaline, see, for example: Mamedov et al. (2004 ▶); Miranda et al. (2008 ▶); Bhosale et al. (2005 ▶); Kanoktanaporn et al. (1980 ▶); Ali et al. (2000 ▶); Veroni et al. (2008 ▶); Zarranz et al. (2004 ▶); Addess et al. (1993 ▶); Mollegaard et al. (2000 ▶).

Experimental

Crystal data

C27H18N4O·2CH4O

M = 478.54

Triclinic,

a = 10.5120 (3) Å

b = 11.4574 (2) Å

c = 11.9983 (2) Å

α = 116.325 (1)°

β = 107.465 (1)°

γ = 95.147 (1)°

V = 1192.81 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100.0 (1) K

0.39 × 0.29 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.876, T max = 0.990

23412 measured reflections

7076 independent reflections

5031 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.182

S = 1.07

7076 reflections

335 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.99 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025269/at2610sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025269/at2610Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C27H18N4O1·2C1H4O1	V = 1192.81 (4) Å3
Mr = 478.54	Z = 2
Triclinic, P1	F000 = 504
Hall symbol: -P 1	Dx = 1.332 Mg m−3
a = 10.5120 (3) Å	Mo Kα radiation λ = 0.71073 Å
b = 11.4574 (2) Å	Cell parameters from 4368 reflections
c = 11.9983 (2) Å	µ = 0.09 mm−1
α = 116.325 (1)º	T = 100.0 (1) K
β = 107.465 (1)º	Block, brown
γ = 95.147 (1)º	0.39 × 0.29 × 0.12 mm

Bruker SMART APEXII CCD area-detector diffractometer	7076 independent reflections
Radiation source: fine-focus sealed tube	5031 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.043
T = 100.0(1) K	θmax = 30.3º
φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −14→14
Tmin = 0.876, Tmax = 0.990	k = −16→16
23412 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.182	w = 1/[σ2(Fo2) + (0.0919P)2 + 0.4066P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
7076 reflections	Δρmax = 0.99 e Å−3
335 parameters	Δρmin = −0.48 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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.

	x	y	z	Uiso*/Ueq
O1	0.43178 (14)	−0.35511 (14)	0.48044 (14)	0.0269 (3)
N1	0.31793 (14)	−0.20440 (14)	0.39691 (14)	0.0206 (3)
N2	0.29306 (14)	0.09233 (14)	0.22570 (14)	0.0190 (3)
N3	0.03863 (14)	0.11984 (14)	0.25061 (14)	0.0201 (3)
N4	0.42131 (14)	−0.09206 (14)	0.32161 (14)	0.0194 (3)
C1	0.53792 (17)	−0.32830 (17)	0.44611 (16)	0.0204 (3)
C2	0.64738 (18)	−0.38570 (17)	0.47042 (17)	0.0230 (3)
H2A	0.6462	−0.4398	0.5096	0.028*
C3	0.75724 (18)	−0.36215 (18)	0.43628 (18)	0.0247 (4)
H3A	0.8303	−0.4001	0.4533	0.030*
C4	0.76027 (18)	−0.28222 (19)	0.37661 (18)	0.0243 (4)
H4A	0.8341	−0.2682	0.3525	0.029*
C5	0.65261 (17)	−0.22384 (18)	0.35341 (17)	0.0220 (3)
H5A	0.6550	−0.1699	0.3143	0.026*
C6	0.54036 (16)	−0.24495 (16)	0.38802 (16)	0.0191 (3)
C7	0.42786 (17)	−0.18162 (16)	0.36860 (16)	0.0189 (3)
C8	0.23639 (17)	−0.12638 (16)	0.36740 (16)	0.0197 (3)
C9	0.10836 (17)	−0.11210 (17)	0.37990 (18)	0.0223 (3)
H9A	0.0684	−0.1577	0.4137	0.027*
C10	0.04485 (18)	−0.02999 (17)	0.34120 (18)	0.0222 (3)
H10A	−0.0393	−0.0193	0.3490	0.027*
C11	0.10607 (16)	0.03970 (16)	0.28893 (16)	0.0190 (3)
C12	0.09500 (16)	0.18353 (16)	0.20112 (16)	0.0186 (3)
C13	0.22417 (16)	0.16765 (16)	0.18646 (16)	0.0182 (3)
C14	0.23573 (16)	0.02835 (16)	0.27780 (16)	0.0184 (3)
C15	0.29957 (17)	−0.05638 (16)	0.31951 (16)	0.0192 (3)
C16	0.01785 (17)	0.27117 (17)	0.16282 (17)	0.0204 (3)
C17	−0.12304 (18)	0.21913 (19)	0.08189 (18)	0.0256 (4)
H17A	−0.1672	0.1312	0.0538	0.031*
C18	−0.1971 (2)	0.2984 (2)	0.0433 (2)	0.0334 (4)
H18A	−0.2905	0.2630	−0.0116	0.040*
C19	−0.1323 (2)	0.4301 (2)	0.0864 (2)	0.0383 (5)
H19A	−0.1819	0.4828	0.0600	0.046*
C20	0.0072 (2)	0.4835 (2)	0.1693 (2)	0.0343 (4)
H20A	0.0502	0.5724	0.1996	0.041*
C21	0.0823 (2)	0.40404 (18)	0.20673 (19)	0.0265 (4)
H21A	0.1758	0.4396	0.2612	0.032*
C22	0.28550 (17)	0.23115 (16)	0.12362 (16)	0.0192 (3)
C23	0.20742 (18)	0.21654 (18)	−0.00052 (17)	0.0228 (3)
H23A	0.1148	0.1690	−0.0437	0.027*
C24	0.2674 (2)	0.27272 (19)	−0.05977 (18)	0.0259 (4)
H24A	0.2151	0.2613	−0.1434	0.031*
C25	0.4040 (2)	0.34550 (19)	0.00426 (19)	0.0281 (4)
H25A	0.4436	0.3834	−0.0358	0.034*
C26	0.4826 (2)	0.36194 (19)	0.12905 (19)	0.0278 (4)
H26A	0.5745	0.4117	0.1729	0.033*
C27	0.42355 (18)	0.30390 (18)	0.18805 (17)	0.0229 (3)
H27A	0.4765	0.3137	0.2707	0.028*
O2	0.62482 (16)	0.01159 (16)	0.26543 (16)	0.0394 (4)
H1O2	0.7056	0.0933	0.3188	0.059*
C28	0.5765 (2)	0.0070 (2)	0.1395 (2)	0.0398 (5)
H28A	0.5578	0.0915	0.1519	0.060*
H28B	0.4933	−0.0643	0.0802	0.060*
H28C	0.6455	−0.0093	0.1012	0.060*
O3	0.86046 (15)	0.20926 (15)	0.38666 (16)	0.0366 (3)
H1O3	0.9203	0.1858	0.3389	0.055*
C29	0.8398 (2)	0.3352 (2)	0.4050 (2)	0.0352 (4)
H29A	0.8729	0.3989	0.4994	0.053*
H29B	0.7430	0.3260	0.3642	0.053*
H29C	0.8893	0.3665	0.3638	0.053*
H1N4	0.492 (3)	−0.053 (2)	0.302 (2)	0.038 (6)*
H1O1	0.370 (3)	−0.303 (3)	0.460 (3)	0.054 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0281 (6)	0.0313 (7)	0.0364 (7)	0.0112 (5)	0.0177 (6)	0.0248 (6)
N1	0.0209 (7)	0.0221 (7)	0.0245 (7)	0.0066 (5)	0.0106 (6)	0.0146 (6)
N2	0.0215 (7)	0.0202 (7)	0.0182 (6)	0.0051 (5)	0.0090 (5)	0.0111 (5)
N3	0.0213 (7)	0.0201 (7)	0.0202 (7)	0.0055 (5)	0.0087 (5)	0.0105 (6)
N4	0.0202 (6)	0.0226 (7)	0.0216 (7)	0.0074 (5)	0.0098 (5)	0.0145 (6)
C1	0.0228 (8)	0.0198 (8)	0.0193 (7)	0.0028 (6)	0.0083 (6)	0.0105 (6)
C2	0.0263 (8)	0.0219 (8)	0.0228 (8)	0.0069 (6)	0.0071 (7)	0.0140 (7)
C3	0.0231 (8)	0.0260 (9)	0.0254 (8)	0.0082 (7)	0.0069 (7)	0.0141 (7)
C4	0.0201 (8)	0.0305 (9)	0.0256 (8)	0.0065 (7)	0.0096 (7)	0.0161 (7)
C5	0.0215 (8)	0.0260 (8)	0.0223 (8)	0.0059 (6)	0.0089 (6)	0.0147 (7)
C6	0.0198 (7)	0.0200 (7)	0.0187 (7)	0.0044 (6)	0.0069 (6)	0.0109 (6)
C7	0.0207 (7)	0.0193 (7)	0.0180 (7)	0.0040 (6)	0.0077 (6)	0.0104 (6)
C8	0.0205 (7)	0.0198 (8)	0.0212 (8)	0.0039 (6)	0.0087 (6)	0.0118 (6)
C9	0.0226 (8)	0.0239 (8)	0.0263 (8)	0.0053 (6)	0.0130 (7)	0.0151 (7)
C10	0.0210 (8)	0.0247 (8)	0.0260 (8)	0.0067 (6)	0.0131 (7)	0.0139 (7)
C11	0.0198 (7)	0.0194 (7)	0.0183 (7)	0.0052 (6)	0.0079 (6)	0.0092 (6)
C12	0.0199 (7)	0.0190 (7)	0.0173 (7)	0.0057 (6)	0.0073 (6)	0.0090 (6)
C13	0.0197 (7)	0.0182 (7)	0.0166 (7)	0.0040 (6)	0.0067 (6)	0.0087 (6)
C14	0.0208 (7)	0.0192 (7)	0.0170 (7)	0.0053 (6)	0.0083 (6)	0.0097 (6)
C15	0.0201 (7)	0.0208 (8)	0.0192 (7)	0.0058 (6)	0.0088 (6)	0.0108 (6)
C16	0.0227 (8)	0.0235 (8)	0.0204 (8)	0.0107 (6)	0.0115 (6)	0.0122 (7)
C17	0.0251 (8)	0.0276 (9)	0.0245 (8)	0.0086 (7)	0.0089 (7)	0.0132 (7)
C18	0.0288 (9)	0.0418 (11)	0.0305 (10)	0.0166 (8)	0.0081 (8)	0.0192 (9)
C19	0.0429 (12)	0.0403 (12)	0.0442 (12)	0.0252 (10)	0.0182 (10)	0.0275 (10)
C20	0.0423 (11)	0.0266 (9)	0.0430 (11)	0.0150 (8)	0.0196 (9)	0.0213 (9)
C21	0.0288 (9)	0.0237 (8)	0.0298 (9)	0.0095 (7)	0.0129 (7)	0.0140 (7)
C22	0.0233 (8)	0.0187 (7)	0.0203 (8)	0.0076 (6)	0.0110 (6)	0.0113 (6)
C23	0.0238 (8)	0.0249 (8)	0.0225 (8)	0.0078 (7)	0.0094 (7)	0.0133 (7)
C24	0.0334 (9)	0.0288 (9)	0.0223 (8)	0.0096 (7)	0.0117 (7)	0.0170 (7)
C25	0.0378 (10)	0.0259 (9)	0.0283 (9)	0.0061 (7)	0.0169 (8)	0.0172 (8)
C26	0.0283 (9)	0.0262 (9)	0.0265 (9)	0.0001 (7)	0.0114 (7)	0.0116 (7)
C27	0.0248 (8)	0.0252 (8)	0.0201 (8)	0.0053 (7)	0.0091 (6)	0.0121 (7)
O2	0.0436 (8)	0.0401 (8)	0.0442 (9)	0.0048 (7)	0.0230 (7)	0.0259 (7)
C28	0.0470 (12)	0.0376 (11)	0.0423 (12)	0.0138 (10)	0.0216 (10)	0.0224 (10)
O3	0.0404 (8)	0.0427 (8)	0.0511 (9)	0.0215 (7)	0.0308 (7)	0.0324 (8)
C29	0.0345 (10)	0.0341 (10)	0.0416 (11)	0.0129 (8)	0.0216 (9)	0.0172 (9)

O1—C1	1.355 (2)	C16—C21	1.394 (2)
O1—H1O1	0.97 (3)	C16—C17	1.399 (2)
N1—C7	1.334 (2)	C17—C18	1.389 (3)
N1—C8	1.377 (2)	C17—H17A	0.9300
N2—C13	1.326 (2)	C18—C19	1.386 (3)
N2—C14	1.358 (2)	C18—H18A	0.9300
N3—C12	1.324 (2)	C19—C20	1.392 (3)
N3—C11	1.361 (2)	C19—H19A	0.9300
N4—C7	1.370 (2)	C20—C21	1.390 (3)
N4—C15	1.374 (2)	C20—H20A	0.9300
N4—H1N4	0.97 (3)	C21—H21A	0.9300
C1—C2	1.395 (2)	C22—C27	1.392 (2)
C1—C6	1.412 (2)	C22—C23	1.393 (2)
C2—C3	1.379 (3)	C23—C24	1.385 (2)
C2—H2A	0.9300	C23—H23A	0.9300
C3—C4	1.394 (2)	C24—C25	1.380 (3)
C3—H3A	0.9300	C24—H24A	0.9300
C4—C5	1.385 (2)	C25—C26	1.392 (3)
C4—H4A	0.9300	C25—H25A	0.9300
C5—C6	1.398 (2)	C26—C27	1.391 (2)
C5—H5A	0.9300	C26—H26A	0.9300
C6—C7	1.455 (2)	C27—H27A	0.9300
C8—C15	1.399 (2)	O2—C28	1.416 (3)
C8—C9	1.414 (2)	O2—H1O2	1.0039
C9—C10	1.364 (2)	C28—H28A	0.9600
C9—H9A	0.9300	C28—H28B	0.9600
C10—C11	1.428 (2)	C28—H28C	0.9600
C10—H10A	0.9300	O3—C29	1.407 (2)
C11—C14	1.421 (2)	O3—H1O3	0.9522
C12—C13	1.438 (2)	C29—H29A	0.9600
C12—C16	1.486 (2)	C29—H29B	0.9600
C13—C22	1.486 (2)	C29—H29C	0.9600
C14—C15	1.410 (2)
Cg1···Cg1i	3.7885 (10)	Cg3···Cg4i	3.6348 (11)
Cg2···Cg3i	3.5234 (7)
C1—O1—H1O1	104.8 (17)	C8—C15—C14	121.14 (15)
C7—N1—C8	105.76 (13)	C21—C16—C17	119.42 (16)
C13—N2—C14	117.55 (14)	C21—C16—C12	121.54 (15)
C12—N3—C11	118.73 (14)	C17—C16—C12	119.04 (15)
C7—N4—C15	106.63 (14)	C18—C17—C16	120.17 (17)
C7—N4—H1N4	127.7 (14)	C18—C17—H17A	119.9
C15—N4—H1N4	125.4 (14)	C16—C17—H17A	119.9
O1—C1—C2	117.77 (15)	C19—C18—C17	120.15 (19)
O1—C1—C6	122.16 (15)	C19—C18—H18A	119.9
C2—C1—C6	120.07 (15)	C17—C18—H18A	119.9
C3—C2—C1	119.88 (16)	C18—C19—C20	120.00 (18)
C3—C2—H2A	120.1	C18—C19—H19A	120.0
C1—C2—H2A	120.1	C20—C19—H19A	120.0
C2—C3—C4	120.86 (16)	C21—C20—C19	120.10 (19)
C2—C3—H3A	119.6	C21—C20—H20A	119.9
C4—C3—H3A	119.6	C19—C20—H20A	119.9
C5—C4—C3	119.55 (16)	C20—C21—C16	120.13 (18)
C5—C4—H4A	120.2	C20—C21—H21A	119.9
C3—C4—H4A	120.2	C16—C21—H21A	119.9
C4—C5—C6	120.87 (16)	C27—C22—C23	119.41 (15)
C4—C5—H5A	119.6	C27—C22—C13	119.70 (14)
C6—C5—H5A	119.6	C23—C22—C13	120.88 (15)
C5—C6—C1	118.74 (15)	C24—C23—C22	120.17 (16)
C5—C6—C7	122.07 (15)	C24—C23—H23A	119.9
C1—C6—C7	119.18 (15)	C22—C23—H23A	119.9
N1—C7—N4	111.95 (14)	C25—C24—C23	120.52 (16)
N1—C7—C6	122.72 (14)	C25—C24—H24A	119.7
N4—C7—C6	125.33 (15)	C23—C24—H24A	119.7
N1—C8—C15	109.29 (14)	C24—C25—C26	119.76 (16)
N1—C8—C9	129.16 (15)	C24—C25—H25A	120.1
C15—C8—C9	121.56 (15)	C26—C25—H25A	120.1
C10—C9—C8	118.49 (15)	C27—C26—C25	119.98 (17)
C10—C9—H9A	120.8	C27—C26—H26A	120.0
C8—C9—H9A	120.8	C25—C26—H26A	120.0
C9—C10—C11	120.76 (15)	C26—C27—C22	120.16 (16)
C9—C10—H10A	119.6	C26—C27—H27A	119.9
C11—C10—H10A	119.6	C22—C27—H27A	119.9
N3—C11—C14	119.68 (14)	C28—O2—H1O2	101.2
N3—C11—C10	118.80 (15)	O2—C28—H28A	109.5
C14—C11—C10	121.51 (15)	O2—C28—H28B	109.5
N3—C12—C13	120.96 (14)	H28A—C28—H28B	109.5
N3—C12—C16	116.40 (14)	O2—C28—H28C	109.5
C13—C12—C16	122.65 (14)	H28A—C28—H28C	109.5
N2—C13—C12	121.33 (14)	H28B—C28—H28C	109.5
N2—C13—C22	116.56 (14)	C29—O3—H1O3	108.4
C12—C13—C22	122.09 (14)	O3—C29—H29A	109.5
N2—C14—C15	121.75 (15)	O3—C29—H29B	109.5
N2—C14—C11	121.71 (15)	H29A—C29—H29B	109.5
C15—C14—C11	116.51 (14)	O3—C29—H29C	109.5
N4—C15—C8	106.38 (14)	H29A—C29—H29C	109.5
N4—C15—C14	132.46 (15)	H29B—C29—H29C	109.5
O1—C1—C2—C3	179.52 (16)	N3—C11—C14—N2	−2.1 (2)
C6—C1—C2—C3	−0.7 (3)	C10—C11—C14—N2	178.68 (15)
C1—C2—C3—C4	−0.5 (3)	N3—C11—C14—C15	179.95 (14)
C2—C3—C4—C5	1.1 (3)	C10—C11—C14—C15	0.7 (2)
C3—C4—C5—C6	−0.5 (3)	C7—N4—C15—C8	0.49 (17)
C4—C5—C6—C1	−0.6 (3)	C7—N4—C15—C14	−177.94 (17)
C4—C5—C6—C7	178.09 (16)	N1—C8—C15—N4	−0.57 (18)
O1—C1—C6—C5	−179.00 (15)	C9—C8—C15—N4	179.39 (15)
C2—C1—C6—C5	1.3 (2)	N1—C8—C15—C14	178.09 (15)
O1—C1—C6—C7	2.3 (2)	C9—C8—C15—C14	−2.0 (3)
C2—C1—C6—C7	−177.50 (15)	N2—C14—C15—N4	1.1 (3)
C8—N1—C7—N4	−0.09 (19)	C11—C14—C15—N4	179.09 (17)
C8—N1—C7—C6	179.25 (15)	N2—C14—C15—C8	−177.11 (15)
C15—N4—C7—N1	−0.26 (19)	C11—C14—C15—C8	0.8 (2)
C15—N4—C7—C6	−179.58 (15)	N3—C12—C16—C21	129.81 (17)
C5—C6—C7—N1	177.68 (16)	C13—C12—C16—C21	−50.0 (2)
C1—C6—C7—N1	−3.6 (2)	N3—C12—C16—C17	−49.6 (2)
C5—C6—C7—N4	−3.1 (3)	C13—C12—C16—C17	130.63 (17)
C1—C6—C7—N4	175.63 (15)	C21—C16—C17—C18	1.4 (3)
C7—N1—C8—C15	0.41 (18)	C12—C16—C17—C18	−179.21 (17)
C7—N1—C8—C9	−179.54 (17)	C16—C17—C18—C19	−0.9 (3)
N1—C8—C9—C10	−178.63 (17)	C17—C18—C19—C20	−0.4 (3)
C15—C8—C9—C10	1.4 (3)	C18—C19—C20—C21	1.3 (3)
C8—C9—C10—C11	0.2 (3)	C19—C20—C21—C16	−0.8 (3)
C12—N3—C11—C14	1.3 (2)	C17—C16—C21—C20	−0.6 (3)
C12—N3—C11—C10	−179.45 (15)	C12—C16—C21—C20	−179.91 (17)
C9—C10—C11—N3	179.52 (16)	N2—C13—C22—C27	−50.5 (2)
C9—C10—C11—C14	−1.3 (3)	C12—C13—C22—C27	131.08 (17)
C11—N3—C12—C13	0.7 (2)	N2—C13—C22—C23	128.11 (17)
C11—N3—C12—C16	−179.14 (14)	C12—C13—C22—C23	−50.3 (2)
C14—N2—C13—C12	1.3 (2)	C27—C22—C23—C24	0.7 (3)
C14—N2—C13—C22	−177.07 (14)	C13—C22—C23—C24	−177.91 (16)
N3—C12—C13—N2	−2.1 (2)	C22—C23—C24—C25	−1.1 (3)
C16—C12—C13—N2	177.70 (15)	C23—C24—C25—C26	0.4 (3)
N3—C12—C13—C22	176.20 (15)	C24—C25—C26—C27	0.7 (3)
C16—C12—C13—C22	−4.0 (2)	C25—C26—C27—C22	−1.0 (3)
C13—N2—C14—C15	178.55 (15)	C23—C22—C27—C26	0.3 (3)
C13—N2—C14—C11	0.7 (2)	C13—C22—C27—C26	178.97 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O3	1.00	1.71	2.700 (3)	167
O3—H1O3···N3ii	0.95	1.87	2.814 (2)	172
N4—H1N4···O2	0.97 (3)	1.78 (3)	2.750 (2)	177 (2)
O1—H1O1···N1	0.97 (4)	1.66 (4)	2.570 (2)	154 (3)
C2—H2A···O1iii	0.93	2.48	3.356 (3)	156
C5—H5A···O2	0.93	2.42	3.310 (3)	160
C28—H28C···Cg5iv	0.96	2.95	3.534 (2)	120

Table 1

Selected centroid⋯centroid distances (Å)

Cg1⋯Cg1i	3.7885 (10)
Cg2⋯Cg3i	3.5234 (7)
Cg3⋯Cg4i	3.6348 (11)

Symmetry code: (i) . Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1/N4/C7/C8/C15, N2/N3/C11–C14, C1–C6 and C8–C15 benzene rings, respectively.

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O3	1.00	1.71	2.700 (3)	167
O3—H1O3⋯N3iii	0.95	1.87	2.814 (2)	172
N4—H1N4⋯O2	0.97 (3)	1.78 (3)	2.750 (2)	177 (2)
O1—H1O1⋯N1	0.97 (4)	1.66 (4)	2.570 (2)	154 (3)
C2—H2A⋯O1iv	0.93	2.48	3.356 (3)	156
C5—H5A⋯O2	0.93	2.42	3.310 (3)	160
C28—H28C⋯Cg5v	0.96	2.95	3.534 (2)	120

Symmetry codes: (iii) ; (iv) ; (v) . Cg5 is the centroid of the C22–C27 benzene ring.