Crystal structure of (E)-N-{[3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]methyl-idene}hydroxyl-amine.

The title compound, C15H14N4O, crystallizes with two mol-ecules in the asymmetric unit with similar conformations (r.m.s. overlay fit for the 20 non-H atoms = 0.175 Å). In the first mol-ecule, the dihedral angles between the planes of the central pyrazole ring and the pendant phenyl and pyrrole rings are 42.69 (8) and 51.88 (6)°, respectively, with corresponding angles of 54.49 (7) and 49.61 (9)°, respectively, in the second mol-ecule. In the crystal, the two mol-ecules, together with their inversion-symmetry counterparts, are linked into tetra-mers by O-H⋯N hydrogen bonds. The tetra-mers form layers parallel to (211) through pairwise C-H⋯π inter-actions.

Related literature

For use of pyrazoles in synthesis of polyfunctionally substituted heterocycles, see: Elnagdi et al. (1987 ▶); Quiroga et al. (2007 ▶, 2008 ▶); Aly et al. (1994 ▶). For pharmaceutical properties of pyrazole-containing compounds, see: Bazgir et al. (2008 ▶); Dias et al. (1994 ▶); El-Kashef et al. (2000 ▶); El-Emary et al. (2002 ▶).

Experimental

Crystal data

C15H14N4O

M = 266.30

Triclinic,

a = 9.1497 (2) Å

b = 12.3932 (3) Å

c = 12.7294 (3) Å

α = 87.4070 (11)°

β = 82.6740 (12)°

γ = 75.0190 (12)°

V = 1382.88 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.68 mm−1

T = 150 K

0.22 × 0.15 × 0.05 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2014 ▶) T min = 0.92, T max = 0.97

15570 measured reflections

5370 independent reflections

4088 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.108

S = 1.04

5370 reflections

363 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2014 ▶); cell refinement: SAINT (Bruker, 2014 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814023514/hb7307sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814023514/hb7307Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814023514/hb7307Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814023514/hb7307fig1.tif

The asymmetric unit of the title compound with 50% probability ellipsoids.

Click here for additional data file.

a . DOI: 10.1107/S1600536814023514/hb7307fig2.tif

Packing of three H-bonded tetra­mers viewed down the a axis. O—H⋯N hydrogen bonds are shown by dotted lines.

Click here for additional data file.

. DOI: 10.1107/S1600536814023514/hb7307fig3.tif

Elevation view of the layers of H-bonded tetra­mers.

CCDC reference: 1031015

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H14N4O	Z = 4
Mr = 266.30	F(000) = 560
Triclinic, P1	Dx = 1.279 Mg m−3
a = 9.1497 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 12.3932 (3) Å	Cell parameters from 8765 reflections
c = 12.7294 (3) Å	θ = 3.5–72.2°
α = 87.4070 (11)°	µ = 0.68 mm−1
β = 82.6740 (12)°	T = 150 K
γ = 75.0190 (12)°	Plate, colourless
V = 1382.88 (6) Å3	0.22 × 0.15 × 0.05 mm

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	5370 independent reflections
Radiation source: INCOATEC IµS micro-focus source	4088 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.036
Detector resolution: 10.4167 pixels mm-1	θmax = 72.4°, θmin = 3.5°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −15→15
Tmin = 0.92, Tmax = 0.97	l = −15→15
15570 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: mixed
wR(F2) = 0.108	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0468P)2 + 0.401P] where P = (Fo2 + 2Fc2)/3
5370 reflections	(Δ/σ)max = 0.001
363 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. H-atoms attached to carbonwere placed in calculated positions (C—H = 0.95 - 0.98 Å) while thoseattached to oxygen were placed in locations derived from a differencemap and their parameters adjusted to give O—H = 0.84 Å. All wereincluded as riding contributions with isotropic displacementparameters 1.2 - 1.5 times those of the attached atoms.

	x	y	z	Uiso*/Ueq
O1	0.01620 (14)	−0.14968 (11)	1.23494 (9)	0.0350 (3)
H1A	0.0512	−0.2083	1.2691	0.042*
N1	0.32895 (16)	0.00206 (11)	0.85512 (11)	0.0253 (3)
N2	0.33432 (17)	−0.10531 (12)	0.83004 (11)	0.0283 (3)
N3	0.23015 (16)	0.13164 (11)	0.99916 (11)	0.0265 (3)
N4	0.11882 (17)	−0.16601 (13)	1.14130 (11)	0.0305 (3)
N5	0.86241 (16)	0.34350 (11)	0.53889 (10)	0.0260 (3)
C1	0.40366 (18)	0.06699 (13)	0.78205 (13)	0.0252 (3)
C2	0.39036 (19)	0.06265 (14)	0.67514 (13)	0.0281 (4)
H2	0.3287	0.0198	0.6516	0.034*
C3	0.4681 (2)	0.12150 (15)	0.60299 (14)	0.0318 (4)
H3	0.4610	0.1181	0.5295	0.038*
C4	0.5558 (2)	0.18502 (15)	0.63761 (15)	0.0332 (4)
H4	0.6089	0.2251	0.5878	0.040*
C5	0.5667 (2)	0.19049 (15)	0.74439 (15)	0.0323 (4)
H5	0.6256	0.2356	0.7678	0.039*
C6	0.49199 (19)	0.13047 (14)	0.81776 (14)	0.0294 (4)
H6	0.5011	0.1328	0.8911	0.035*
C7	0.25257 (19)	0.02755 (14)	0.95310 (13)	0.0248 (3)
C8	0.20937 (19)	−0.06590 (14)	0.99446 (13)	0.0256 (3)
C9	0.2641 (2)	−0.14714 (14)	0.91388 (13)	0.0282 (4)
C10	0.2486 (3)	−0.26404 (15)	0.91273 (16)	0.0423 (5)
H10A	0.2917	−0.2969	0.8434	0.063*
H10B	0.1406	−0.2636	0.9260	0.063*
H10C	0.3034	−0.3084	0.9680	0.063*
C11	0.2741 (3)	0.14651 (16)	1.09638 (15)	0.0413 (5)
H11	0.3152	0.0889	1.1443	0.050*
C12	0.2485 (3)	0.25693 (18)	1.11112 (17)	0.0558 (6)
H12	0.2681	0.2911	1.1713	0.067*
C13	0.1869 (3)	0.31322 (15)	1.02105 (16)	0.0416 (5)
H13	0.1580	0.3918	1.0101	0.050*
C14	0.1765 (2)	0.23523 (14)	0.95337 (14)	0.0295 (4)
H14	0.1392	0.2492	0.8865	0.035*
C15	0.1185 (2)	−0.07129 (14)	1.09604 (13)	0.0273 (4)
H15	0.0587	−0.0044	1.1291	0.033*
O2	0.49919 (16)	0.78935 (10)	0.64738 (10)	0.0386 (3)
H2A	0.4532	0.8172	0.7052	0.046*
N6	0.84165 (17)	0.33808 (12)	0.64741 (11)	0.0284 (3)
N7	0.79776 (16)	0.47398 (11)	0.39594 (11)	0.0261 (3)
N8	0.56651 (17)	0.67789 (12)	0.67161 (12)	0.0315 (3)
C16	0.94172 (19)	0.24537 (13)	0.47988 (13)	0.0257 (4)
C17	1.0867 (2)	0.18970 (15)	0.50007 (14)	0.0334 (4)
H17	1.1349	0.2169	0.5513	0.040*
C18	1.1611 (2)	0.09363 (17)	0.44459 (15)	0.0391 (5)
H18	1.2611	0.0546	0.4578	0.047*
C19	1.0912 (2)	0.05402 (16)	0.37017 (15)	0.0362 (4)
H19	1.1428	−0.0123	0.3327	0.043*
C20	0.9459 (2)	0.11116 (16)	0.35027 (14)	0.0340 (4)
H20	0.8981	0.0843	0.2987	0.041*
C21	0.8700 (2)	0.20730 (15)	0.40525 (13)	0.0302 (4)
H21	0.7702	0.2466	0.3919	0.036*
C22	0.78947 (19)	0.44542 (14)	0.50370 (13)	0.0255 (3)
C23	0.7165 (2)	0.50922 (14)	0.59080 (13)	0.0266 (4)
C24	0.7529 (2)	0.43701 (14)	0.67857 (13)	0.0284 (4)
C25	0.7069 (2)	0.45931 (16)	0.79421 (14)	0.0374 (4)
H25A	0.7502	0.3924	0.8352	0.056*
H25B	0.5955	0.4784	0.8089	0.056*
H25C	0.7447	0.5216	0.8142	0.056*
C26	0.6762 (2)	0.52578 (16)	0.34263 (14)	0.0352 (4)
H26	0.5721	0.5447	0.3718	0.042*
C27	0.7302 (2)	0.54509 (17)	0.24161 (15)	0.0400 (5)
H27	0.6712	0.5800	0.1874	0.048*
C28	0.8895 (2)	0.5042 (2)	0.23135 (16)	0.0507 (6)
H28	0.9576	0.5067	0.1689	0.061*
C29	0.9289 (2)	0.46064 (19)	0.32625 (16)	0.0435 (5)
H29	1.0294	0.4268	0.3420	0.052*
C30	0.6353 (2)	0.62612 (14)	0.58742 (14)	0.0304 (4)
H30	0.6330	0.6651	0.5214	0.036*

	U11	U22	U33	U12	U13	U23
O1	0.0406 (7)	0.0345 (7)	0.0262 (6)	−0.0060 (6)	0.0012 (5)	0.0040 (5)
N1	0.0317 (8)	0.0214 (7)	0.0232 (7)	−0.0070 (6)	−0.0033 (6)	−0.0022 (5)
N2	0.0361 (8)	0.0216 (7)	0.0272 (7)	−0.0071 (6)	−0.0033 (6)	−0.0031 (6)
N3	0.0352 (8)	0.0225 (7)	0.0221 (7)	−0.0070 (6)	−0.0049 (6)	−0.0021 (5)
N4	0.0335 (8)	0.0375 (9)	0.0211 (7)	−0.0105 (7)	−0.0022 (6)	−0.0008 (6)
N5	0.0319 (8)	0.0248 (7)	0.0210 (7)	−0.0067 (6)	−0.0034 (6)	0.0009 (5)
C1	0.0248 (8)	0.0224 (8)	0.0262 (8)	−0.0032 (7)	−0.0008 (7)	0.0002 (6)
C2	0.0308 (9)	0.0255 (9)	0.0271 (9)	−0.0056 (7)	−0.0036 (7)	−0.0011 (7)
C3	0.0325 (10)	0.0320 (10)	0.0266 (9)	−0.0020 (8)	−0.0007 (7)	0.0019 (7)
C4	0.0292 (9)	0.0271 (9)	0.0389 (10)	−0.0035 (7)	0.0020 (8)	0.0066 (8)
C5	0.0253 (9)	0.0273 (9)	0.0446 (11)	−0.0074 (7)	−0.0051 (8)	0.0026 (8)
C6	0.0285 (9)	0.0275 (9)	0.0316 (9)	−0.0044 (7)	−0.0063 (7)	−0.0008 (7)
C7	0.0286 (9)	0.0231 (8)	0.0221 (8)	−0.0038 (7)	−0.0059 (6)	−0.0010 (6)
C8	0.0298 (9)	0.0232 (8)	0.0239 (8)	−0.0057 (7)	−0.0063 (7)	0.0008 (6)
C9	0.0351 (9)	0.0237 (9)	0.0260 (9)	−0.0076 (7)	−0.0045 (7)	0.0001 (7)
C10	0.0643 (14)	0.0278 (10)	0.0358 (11)	−0.0178 (9)	0.0049 (9)	−0.0050 (8)
C11	0.0660 (14)	0.0312 (10)	0.0289 (10)	−0.0105 (9)	−0.0182 (9)	−0.0006 (8)
C12	0.100 (2)	0.0328 (11)	0.0399 (12)	−0.0157 (12)	−0.0292 (12)	−0.0059 (9)
C13	0.0635 (14)	0.0210 (9)	0.0393 (11)	−0.0074 (9)	−0.0091 (9)	−0.0023 (8)
C14	0.0363 (10)	0.0240 (9)	0.0266 (9)	−0.0051 (7)	−0.0037 (7)	0.0013 (7)
C15	0.0331 (9)	0.0254 (9)	0.0236 (8)	−0.0060 (7)	−0.0069 (7)	0.0003 (7)
O2	0.0537 (8)	0.0263 (7)	0.0283 (7)	−0.0002 (6)	0.0026 (6)	−0.0024 (5)
N6	0.0396 (8)	0.0255 (7)	0.0213 (7)	−0.0102 (6)	−0.0049 (6)	0.0012 (6)
N7	0.0287 (8)	0.0253 (7)	0.0227 (7)	−0.0046 (6)	−0.0028 (6)	0.0021 (5)
N8	0.0392 (9)	0.0228 (7)	0.0317 (8)	−0.0064 (6)	−0.0045 (6)	−0.0008 (6)
C16	0.0295 (9)	0.0224 (8)	0.0238 (8)	−0.0054 (7)	−0.0012 (7)	0.0010 (6)
C17	0.0337 (10)	0.0336 (10)	0.0328 (10)	−0.0055 (8)	−0.0095 (8)	−0.0031 (8)
C18	0.0331 (10)	0.0384 (11)	0.0403 (11)	0.0039 (8)	−0.0095 (8)	−0.0042 (8)
C19	0.0395 (11)	0.0302 (10)	0.0338 (10)	−0.0001 (8)	−0.0011 (8)	−0.0070 (8)
C20	0.0373 (10)	0.0365 (10)	0.0281 (9)	−0.0086 (8)	−0.0033 (8)	−0.0079 (8)
C21	0.0270 (9)	0.0333 (10)	0.0294 (9)	−0.0048 (8)	−0.0049 (7)	−0.0028 (7)
C22	0.0273 (9)	0.0241 (8)	0.0249 (8)	−0.0067 (7)	−0.0033 (7)	0.0021 (6)
C23	0.0318 (9)	0.0236 (8)	0.0254 (8)	−0.0091 (7)	−0.0027 (7)	−0.0010 (7)
C24	0.0377 (10)	0.0235 (8)	0.0255 (9)	−0.0108 (7)	−0.0037 (7)	−0.0010 (7)
C25	0.0563 (13)	0.0294 (10)	0.0258 (9)	−0.0107 (9)	−0.0026 (8)	−0.0015 (7)
C26	0.0284 (9)	0.0405 (11)	0.0315 (10)	−0.0001 (8)	−0.0042 (7)	0.0047 (8)
C27	0.0421 (11)	0.0460 (12)	0.0281 (10)	−0.0041 (9)	−0.0072 (8)	0.0061 (8)
C28	0.0393 (12)	0.0726 (16)	0.0317 (11)	−0.0056 (11)	0.0043 (9)	0.0150 (10)
C29	0.0269 (10)	0.0621 (14)	0.0364 (11)	−0.0069 (9)	−0.0001 (8)	0.0143 (9)
C30	0.0385 (10)	0.0261 (9)	0.0256 (9)	−0.0068 (8)	−0.0029 (7)	−0.0004 (7)

O1—N4	1.4078 (18)	C13—H13	0.9500
O1—H1A	0.8403	C14—H14	0.9500
N1—C7	1.358 (2)	C15—H15	0.9500
N1—N2	1.3695 (18)	O2—N8	1.3973 (18)
N1—C1	1.426 (2)	O2—H2A	0.8402
N2—C9	1.330 (2)	N6—C24	1.329 (2)
N3—C14	1.381 (2)	N7—C29	1.376 (2)
N3—C11	1.383 (2)	N7—C26	1.376 (2)
N3—C7	1.397 (2)	N7—C22	1.399 (2)
N4—C15	1.284 (2)	N8—C30	1.280 (2)
N5—C22	1.353 (2)	C16—C17	1.378 (2)
N5—N6	1.3713 (18)	C16—C21	1.384 (2)
N5—C16	1.434 (2)	C17—C18	1.383 (3)
C1—C2	1.386 (2)	C17—H17	0.9500
C1—C6	1.391 (2)	C18—C19	1.380 (3)
C2—C3	1.387 (2)	C18—H18	0.9500
C2—H2	0.9500	C19—C20	1.385 (3)
C3—C4	1.380 (3)	C19—H19	0.9500
C3—H3	0.9500	C20—C21	1.384 (2)
C4—C5	1.382 (3)	C20—H20	0.9500
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.389 (2)	C22—C23	1.385 (2)
C5—H5	0.9500	C23—C24	1.418 (2)
C6—H6	0.9500	C23—C30	1.449 (2)
C7—C8	1.379 (2)	C24—C25	1.496 (2)
C8—C9	1.421 (2)	C25—H25A	0.9800
C8—C15	1.454 (2)	C25—H25B	0.9800
C9—C10	1.493 (2)	C25—H25C	0.9800
C10—H10A	0.9800	C26—C27	1.351 (3)
C10—H10B	0.9800	C26—H26	0.9500
C10—H10C	0.9800	C27—C28	1.405 (3)
C11—C12	1.345 (3)	C27—H27	0.9500
C11—H11	0.9500	C28—C29	1.353 (3)
C12—C13	1.417 (3)	C28—H28	0.9500
C12—H12	0.9500	C29—H29	0.9500
C13—C14	1.352 (2)	C30—H30	0.9500
N4—O1—H1A	101.0	N4—C15—C8	120.32 (16)
C7—N1—N2	110.52 (13)	N4—C15—H15	119.8
C7—N1—C1	130.19 (14)	C8—C15—H15	119.8
N2—N1—C1	119.25 (13)	N8—O2—H2A	105.0
C9—N2—N1	106.20 (13)	C24—N6—N5	105.80 (13)
C14—N3—C11	108.69 (14)	C29—N7—C26	108.17 (15)
C14—N3—C7	127.03 (14)	C29—N7—C22	126.09 (15)
C11—N3—C7	123.98 (15)	C26—N7—C22	125.65 (15)
C15—N4—O1	109.56 (14)	C30—N8—O2	110.12 (14)
C22—N5—N6	110.63 (13)	C17—C16—C21	121.33 (16)
C22—N5—C16	129.45 (14)	C17—C16—N5	119.32 (15)
N6—N5—C16	119.70 (13)	C21—C16—N5	119.33 (15)
C2—C1—C6	120.97 (15)	C16—C17—C18	118.98 (17)
C2—C1—N1	118.81 (15)	C16—C17—H17	120.5
C6—C1—N1	120.18 (15)	C18—C17—H17	120.5
C1—C2—C3	119.25 (16)	C19—C18—C17	120.55 (18)
C1—C2—H2	120.4	C19—C18—H18	119.7
C3—C2—H2	120.4	C17—C18—H18	119.7
C4—C3—C2	120.24 (17)	C18—C19—C20	119.84 (17)
C4—C3—H3	119.9	C18—C19—H19	120.1
C2—C3—H3	119.9	C20—C19—H19	120.1
C3—C4—C5	120.27 (16)	C21—C20—C19	120.25 (17)
C3—C4—H4	119.9	C21—C20—H20	119.9
C5—C4—H4	119.9	C19—C20—H20	119.9
C4—C5—C6	120.36 (17)	C16—C21—C20	119.05 (16)
C4—C5—H5	119.8	C16—C21—H21	120.5
C6—C5—H5	119.8	C20—C21—H21	120.5
C5—C6—C1	118.88 (16)	N5—C22—C23	108.17 (14)
C5—C6—H6	120.6	N5—C22—N7	121.95 (15)
C1—C6—H6	120.6	C23—C22—N7	129.85 (15)
N1—C7—C8	107.93 (14)	C22—C23—C24	104.11 (15)
N1—C7—N3	122.85 (15)	C22—C23—C30	125.38 (15)
C8—C7—N3	129.20 (15)	C24—C23—C30	130.28 (16)
C7—C8—C9	104.66 (15)	N6—C24—C23	111.28 (15)
C7—C8—C15	125.06 (15)	N6—C24—C25	119.72 (15)
C9—C8—C15	130.16 (15)	C23—C24—C25	129.00 (16)
N2—C9—C8	110.67 (15)	C24—C25—H25A	109.5
N2—C9—C10	120.20 (15)	C24—C25—H25B	109.5
C8—C9—C10	129.11 (16)	H25A—C25—H25B	109.5
C9—C10—H10A	109.5	C24—C25—H25C	109.5
C9—C10—H10B	109.5	H25A—C25—H25C	109.5
H10A—C10—H10B	109.5	H25B—C25—H25C	109.5
C9—C10—H10C	109.5	C27—C26—N7	108.32 (16)
H10A—C10—H10C	109.5	C27—C26—H26	125.8
H10B—C10—H10C	109.5	N7—C26—H26	125.8
C12—C11—N3	107.90 (17)	C26—C27—C28	107.58 (17)
C12—C11—H11	126.1	C26—C27—H27	126.2
N3—C11—H11	126.1	C28—C27—H27	126.2
C11—C12—C13	107.91 (17)	C29—C28—C27	107.87 (18)
C11—C12—H12	126.0	C29—C28—H28	126.1
C13—C12—H12	126.0	C27—C28—H28	126.1
C14—C13—C12	107.91 (17)	C28—C29—N7	108.05 (17)
C14—C13—H13	126.0	C28—C29—H29	126.0
C12—C13—H13	126.0	N7—C29—H29	126.0
C13—C14—N3	107.60 (16)	N8—C30—C23	121.29 (16)
C13—C14—H14	126.2	N8—C30—H30	119.4
N3—C14—H14	126.2	C23—C30—H30	119.4
C7—N1—N2—C9	−1.45 (18)	C22—N5—N6—C24	1.11 (18)
C1—N1—N2—C9	176.40 (14)	C16—N5—N6—C24	−173.96 (14)
C7—N1—C1—C2	−139.98 (18)	C22—N5—C16—C17	130.07 (19)
N2—N1—C1—C2	42.7 (2)	N6—N5—C16—C17	−55.9 (2)
C7—N1—C1—C6	42.0 (3)	C22—N5—C16—C21	−51.1 (2)
N2—N1—C1—C6	−135.32 (16)	N6—N5—C16—C21	122.89 (17)
C6—C1—C2—C3	0.8 (3)	C21—C16—C17—C18	−0.3 (3)
N1—C1—C2—C3	−177.12 (15)	N5—C16—C17—C18	178.50 (16)
C1—C2—C3—C4	−1.0 (3)	C16—C17—C18—C19	0.0 (3)
C2—C3—C4—C5	0.0 (3)	C17—C18—C19—C20	0.4 (3)
C3—C4—C5—C6	1.2 (3)	C18—C19—C20—C21	−0.5 (3)
C4—C5—C6—C1	−1.4 (3)	C17—C16—C21—C20	0.2 (3)
C2—C1—C6—C5	0.4 (3)	N5—C16—C21—C20	−178.57 (16)
N1—C1—C6—C5	178.29 (15)	C19—C20—C21—C16	0.2 (3)
N2—N1—C7—C8	1.27 (19)	N6—N5—C22—C23	−0.78 (19)
C1—N1—C7—C8	−176.28 (16)	C16—N5—C22—C23	173.68 (16)
N2—N1—C7—N3	179.80 (14)	N6—N5—C22—N7	177.44 (14)
C1—N1—C7—N3	2.3 (3)	C16—N5—C22—N7	−8.1 (3)
C14—N3—C7—N1	49.0 (2)	C29—N7—C22—N5	−50.5 (3)
C11—N3—C7—N1	−124.05 (19)	C26—N7—C22—N5	133.17 (18)
C14—N3—C7—C8	−132.8 (2)	C29—N7—C22—C23	127.3 (2)
C11—N3—C7—C8	54.1 (3)	C26—N7—C22—C23	−49.0 (3)
N1—C7—C8—C9	−0.57 (18)	N5—C22—C23—C24	0.14 (19)
N3—C7—C8—C9	−178.98 (16)	N7—C22—C23—C24	−177.89 (17)
N1—C7—C8—C15	−176.83 (15)	N5—C22—C23—C30	175.12 (16)
N3—C7—C8—C15	4.8 (3)	N7—C22—C23—C30	−2.9 (3)
N1—N2—C9—C8	1.07 (19)	N5—N6—C24—C23	−1.01 (19)
N1—N2—C9—C10	179.60 (16)	N5—N6—C24—C25	179.69 (15)
C7—C8—C9—N2	−0.32 (19)	C22—C23—C24—N6	0.6 (2)
C15—C8—C9—N2	175.67 (16)	C30—C23—C24—N6	−174.07 (17)
C7—C8—C9—C10	−178.69 (19)	C22—C23—C24—C25	179.77 (18)
C15—C8—C9—C10	−2.7 (3)	C30—C23—C24—C25	5.1 (3)
C14—N3—C11—C12	0.1 (2)	C29—N7—C26—C27	−0.3 (2)
C7—N3—C11—C12	174.20 (19)	C22—N7—C26—C27	176.57 (17)
N3—C11—C12—C13	0.0 (3)	N7—C26—C27—C28	0.1 (2)
C11—C12—C13—C14	0.0 (3)	C26—C27—C28—C29	0.2 (3)
C12—C13—C14—N3	0.0 (2)	C27—C28—C29—N7	−0.4 (3)
C11—N3—C14—C13	−0.1 (2)	C26—N7—C29—C28	0.5 (2)
C7—N3—C14—C13	−173.97 (17)	C22—N7—C29—C28	−176.44 (18)
O1—N4—C15—C8	−176.70 (14)	O2—N8—C30—C23	179.19 (15)
C7—C8—C15—N4	−160.65 (17)	C22—C23—C30—N8	177.58 (17)
C9—C8—C15—N4	24.1 (3)	C24—C23—C30—N8	−8.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2i	0.84	1.95	2.7835 (19)	174
O1—H1A···N6ii	0.84	1.99	2.8277 (19)	172
C11—H11···Cgii	0.95	3.45	?	170

Table 1

Hydrogen-bond geometry (, )

Cg is centroid of C1C6 ring.

DHA	DH	HA	D A	DHA
O2H2AN2i	0.84	1.95	2.7835(19)	174
O1H1AN6ii	0.84	1.99	2.8277(19)	172
C11H11Cg ii	0.95	3.45	?	170

Symmetry codes: (i) ; (ii) .