(4Z)-4-[(2,6-Diisopropyl-anilino)(phen-yl)methyl-idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

In the title compound, C(29)H(31)N(3)O, the three terminal benzene rings are oriented at dihedral angles of 20.7 (3), 65.8 (3) and 72.6 (3)° with respect to the central pyrazolone ring. Intra-molecular N-H⋯O hydrogen bonding occurs between the imine and carbonyl groups. Inter-molecular C-H⋯π inter-actions are present in the crystal structure.

Related literature

For the catalysis of olefins polymerization by complexes containing N,O-bidentate ligands, see: Wang et al. (1998 ▶); Connor et al. (2003 ▶); Sun et al. (2003 ▶); Lü et al. (2006 ▶). For related structures, see: Wang et al. (2003 ▶); Li et al. (2009 ▶); Xu et al. (2010 ▶).

Experimental

Crystal data

C29H31N3O

M = 437.57

Orthorhombic,

a = 12.9094 (6) Å

b = 10.6947 (5) Å

c = 17.9676 (8) Å

V = 2480.6 (2) Å3

Z = 4

Cu Kα radiation

μ = 0.56 mm−1

T = 110 K

0.6 × 0.5 × 0.4 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.702, T max = 1.00

8437 measured reflections

3755 independent reflections

3643 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.09

3755 reflections

302 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1293 Friedel pairs

Flack parameter: 0.2 (2)

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000602/xu5120sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000602/xu5120Isup2.hkl

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

C29H31N3O	F(000) = 936
Mr = 437.57	Dx = 1.172 Mg m−3
Orthorhombic, Pna21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2n	Cell parameters from 7431 reflections
a = 12.9094 (6) Å	θ = 4.1–71.6°
b = 10.6947 (5) Å	µ = 0.56 mm−1
c = 17.9676 (8) Å	T = 110 K
V = 2480.6 (2) Å3	Parallelpiped, yellow
Z = 4	0.6 × 0.5 × 0.4 mm

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer	3755 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3643 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 16.0690 pixels mm-1	θmax = 71.6°, θmin = 4.8°
ω scans	h = −12→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −13→12
Tmin = 0.702, Tmax = 1.00	l = −22→18
8437 measured reflections

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.080P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
3755 reflections	Δρmax = 0.27 e Å−3
302 parameters	Δρmin = −0.21 e Å−3
1 restraint	Absolute structure: Flack (1983), 1293 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.2 (2)

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
O	0.91287 (8)	0.45238 (12)	0.24514 (7)	0.0298 (3)
N1	0.93713 (10)	0.44539 (12)	0.37452 (8)	0.0264 (3)
N2	0.87895 (11)	0.47065 (13)	0.43864 (8)	0.0277 (3)
N3	0.72027 (10)	0.52807 (13)	0.21416 (8)	0.0249 (3)
H3A	0.7776 (18)	0.502 (2)	0.2066 (14)	0.032 (5)*
C1	0.88237 (12)	0.46862 (13)	0.31018 (10)	0.0252 (3)
C2	0.78251 (11)	0.51329 (14)	0.33598 (10)	0.0243 (3)
C3	0.78841 (12)	0.50848 (14)	0.41567 (10)	0.0252 (3)
C4	0.70441 (13)	0.53150 (18)	0.47178 (11)	0.0333 (4)
H4A	0.7326	0.5214	0.5221	0.050*
H4B	0.6481	0.4714	0.4641	0.050*
H4C	0.6777	0.6167	0.4658	0.050*
C5	1.04093 (11)	0.40332 (14)	0.38254 (10)	0.0274 (3)
C6	1.08976 (13)	0.34062 (15)	0.32476 (11)	0.0316 (4)
H6A	1.0547	0.3269	0.2790	0.038*
C7	1.19107 (14)	0.29789 (16)	0.33456 (12)	0.0368 (4)
H7A	1.2252	0.2554	0.2951	0.044*
C8	1.24239 (13)	0.31699 (16)	0.40159 (11)	0.0361 (4)
H8A	1.3107	0.2861	0.4084	0.043*
C9	1.19329 (14)	0.38119 (17)	0.45825 (12)	0.0365 (4)
H9A	1.2288	0.3956	0.5038	0.044*
C10	1.09248 (13)	0.42494 (17)	0.44944 (10)	0.0326 (4)
H10A	1.0592	0.4691	0.4886	0.039*
C11	0.70334 (12)	0.54389 (14)	0.28638 (9)	0.0227 (3)
C12	0.59977 (12)	0.58874 (14)	0.31176 (9)	0.0250 (3)
C13	0.58906 (14)	0.70320 (16)	0.34759 (11)	0.0330 (4)
H13A	0.6477	0.7557	0.3542	0.040*
C14	0.49253 (15)	0.74109 (18)	0.37387 (12)	0.0407 (4)
H14A	0.4854	0.8194	0.3983	0.049*
C15	0.40749 (14)	0.6652 (2)	0.36452 (13)	0.0447 (5)
H15A	0.3418	0.6910	0.3827	0.054*
C16	0.41744 (14)	0.5512 (2)	0.32857 (13)	0.0438 (5)
H16A	0.3586	0.4989	0.3224	0.053*
C17	0.51324 (13)	0.51316 (17)	0.30150 (11)	0.0322 (4)
H17A	0.5196	0.4357	0.2761	0.039*
C18	0.65579 (11)	0.56969 (14)	0.15362 (9)	0.0234 (3)
C19	0.65238 (11)	0.69774 (14)	0.13647 (9)	0.0260 (3)
C20	0.59414 (11)	0.73324 (15)	0.07474 (10)	0.0285 (3)
H20A	0.5891	0.8193	0.0622	0.034*
C21	0.54324 (11)	0.64521 (16)	0.03119 (10)	0.0296 (3)
H21A	0.5043	0.6714	−0.0109	0.035*
C22	0.54908 (12)	0.51948 (16)	0.04900 (10)	0.0285 (3)
H22A	0.5144	0.4599	0.0187	0.034*
C23	0.60517 (11)	0.47919 (15)	0.11070 (9)	0.0253 (3)
C24	0.71736 (13)	0.79226 (16)	0.17900 (10)	0.0305 (4)
H24A	0.7239	0.7617	0.2314	0.037*
C25	0.82671 (14)	0.79704 (18)	0.14543 (12)	0.0387 (4)
H25A	0.8560	0.7126	0.1442	0.058*
H25B	0.8708	0.8512	0.1760	0.058*
H25C	0.8231	0.8304	0.0947	0.058*
C26	0.66815 (17)	0.92275 (18)	0.18176 (13)	0.0439 (5)
H26A	0.5986	0.9168	0.2034	0.066*
H26B	0.6633	0.9567	0.1312	0.066*
H26C	0.7110	0.9781	0.2124	0.066*
C27	0.61474 (14)	0.34042 (16)	0.12972 (11)	0.0331 (4)
H27A	0.6263	0.3337	0.1846	0.040*
C28	0.7098 (2)	0.2853 (2)	0.09084 (16)	0.0579 (6)
H28A	0.7712	0.3345	0.1038	0.087*
H28B	0.6994	0.2874	0.0368	0.087*
H28C	0.7197	0.1986	0.1070	0.087*
C29	0.5179 (2)	0.2645 (2)	0.11084 (16)	0.0581 (7)
H29A	0.5289	0.1769	0.1247	0.087*
H29B	0.5042	0.2701	0.0573	0.087*
H29C	0.4586	0.2980	0.1384	0.087*

	U11	U22	U33	U12	U13	U23
O	0.0258 (5)	0.0416 (6)	0.0220 (6)	0.0060 (4)	−0.0012 (4)	0.0005 (5)
N1	0.0249 (6)	0.0309 (6)	0.0234 (7)	−0.0021 (5)	−0.0020 (5)	0.0028 (6)
N2	0.0303 (7)	0.0319 (7)	0.0208 (7)	−0.0063 (5)	−0.0024 (5)	0.0025 (6)
N3	0.0206 (6)	0.0307 (7)	0.0233 (7)	0.0047 (5)	−0.0019 (5)	−0.0008 (5)
C1	0.0231 (7)	0.0250 (7)	0.0274 (9)	−0.0023 (5)	−0.0018 (6)	0.0021 (6)
C2	0.0246 (7)	0.0242 (7)	0.0241 (9)	−0.0028 (5)	0.0005 (6)	0.0005 (6)
C3	0.0281 (7)	0.0252 (7)	0.0221 (8)	−0.0054 (6)	−0.0010 (6)	0.0009 (6)
C4	0.0324 (8)	0.0442 (10)	0.0232 (9)	−0.0026 (7)	0.0024 (7)	0.0020 (7)
C5	0.0267 (7)	0.0242 (6)	0.0314 (9)	−0.0038 (5)	−0.0055 (6)	0.0070 (6)
C6	0.0311 (8)	0.0282 (7)	0.0354 (10)	0.0029 (6)	−0.0109 (6)	−0.0003 (7)
C7	0.0336 (9)	0.0310 (8)	0.0459 (12)	0.0070 (7)	−0.0096 (8)	−0.0029 (8)
C8	0.0285 (8)	0.0316 (8)	0.0483 (12)	0.0022 (7)	−0.0113 (8)	0.0074 (7)
C9	0.0327 (8)	0.0411 (9)	0.0355 (10)	−0.0039 (7)	−0.0126 (7)	0.0075 (8)
C10	0.0298 (8)	0.0388 (9)	0.0292 (9)	−0.0037 (6)	−0.0039 (7)	0.0054 (7)
C11	0.0249 (7)	0.0207 (6)	0.0224 (8)	−0.0028 (5)	0.0003 (6)	−0.0002 (6)
C12	0.0266 (7)	0.0290 (7)	0.0194 (8)	0.0020 (5)	0.0012 (6)	0.0054 (6)
C13	0.0383 (9)	0.0283 (8)	0.0324 (9)	0.0034 (6)	0.0065 (7)	0.0028 (7)
C14	0.0475 (10)	0.0383 (8)	0.0363 (10)	0.0168 (7)	0.0092 (9)	0.0069 (9)
C15	0.0309 (9)	0.0629 (12)	0.0403 (11)	0.0185 (8)	0.0105 (7)	0.0127 (9)
C16	0.0273 (8)	0.0613 (12)	0.0428 (12)	−0.0018 (8)	0.0036 (7)	0.0079 (10)
C17	0.0279 (8)	0.0375 (8)	0.0310 (10)	−0.0024 (6)	0.0005 (7)	0.0020 (7)
C18	0.0198 (6)	0.0297 (7)	0.0205 (7)	0.0028 (5)	0.0020 (6)	0.0014 (6)
C19	0.0229 (7)	0.0300 (7)	0.0251 (8)	0.0009 (5)	0.0068 (6)	0.0015 (6)
C20	0.0272 (8)	0.0285 (7)	0.0297 (9)	0.0052 (6)	0.0074 (6)	0.0071 (7)
C21	0.0207 (7)	0.0421 (9)	0.0259 (8)	0.0055 (6)	−0.0001 (6)	0.0081 (7)
C22	0.0229 (7)	0.0365 (8)	0.0262 (9)	−0.0004 (6)	−0.0016 (6)	0.0002 (7)
C23	0.0224 (6)	0.0304 (8)	0.0231 (8)	0.0007 (5)	0.0014 (6)	0.0004 (6)
C24	0.0336 (8)	0.0295 (8)	0.0283 (9)	−0.0029 (6)	0.0052 (7)	−0.0005 (6)
C25	0.0325 (8)	0.0419 (9)	0.0418 (11)	−0.0094 (7)	0.0048 (8)	−0.0044 (8)
C26	0.0485 (11)	0.0328 (9)	0.0504 (13)	−0.0002 (7)	0.0082 (9)	−0.0057 (9)
C27	0.0433 (9)	0.0287 (8)	0.0272 (9)	−0.0015 (7)	−0.0068 (7)	0.0003 (7)
C28	0.0776 (16)	0.0373 (10)	0.0587 (16)	0.0200 (10)	0.0137 (12)	−0.0005 (10)
C29	0.0722 (15)	0.0434 (11)	0.0586 (15)	−0.0228 (10)	−0.0260 (12)	0.0142 (11)

O—C1	1.245 (2)	C15—H15A	0.9500
N1—C1	1.378 (2)	C16—C17	1.390 (3)
N1—N2	1.402 (2)	C16—H16A	0.9500
N1—C5	1.421 (2)	C17—H17A	0.9500
N2—C3	1.304 (2)	C18—C19	1.404 (2)
N3—C11	1.327 (2)	C18—C23	1.400 (2)
N3—C18	1.440 (2)	C19—C20	1.393 (2)
N3—H3A	0.80 (2)	C19—C24	1.520 (2)
C1—C2	1.451 (2)	C20—C21	1.389 (3)
C2—C11	1.395 (2)	C20—H20A	0.9500
C2—C3	1.435 (2)	C21—C22	1.384 (2)
C3—C4	1.501 (2)	C21—H21A	0.9500
C4—H4A	0.9800	C22—C23	1.392 (2)
C4—H4B	0.9800	C22—H22A	0.9500
C4—H4C	0.9800	C23—C27	1.528 (2)
C5—C6	1.387 (3)	C24—C25	1.536 (2)
C5—C10	1.393 (2)	C24—C26	1.534 (2)
C6—C7	1.397 (2)	C24—H24A	1.0000
C6—H6A	0.9500	C25—H25A	0.9800
C7—C8	1.390 (3)	C25—H25B	0.9800
C7—H7A	0.9500	C25—H25C	0.9800
C8—C9	1.382 (3)	C26—H26A	0.9800
C8—H8A	0.9500	C26—H26B	0.9800
C9—C10	1.392 (3)	C26—H26C	0.9800
C9—H9A	0.9500	C27—C28	1.531 (3)
C10—H10A	0.9500	C27—C29	1.529 (3)
C11—C12	1.492 (2)	C27—H27A	1.0000
C12—C13	1.390 (2)	C28—H28A	0.9800
C12—C17	1.391 (2)	C28—H28B	0.9800
C13—C14	1.393 (2)	C28—H28C	0.9800
C13—H13A	0.9500	C29—H29A	0.9800
C14—C15	1.375 (3)	C29—H29B	0.9800
C14—H14A	0.9500	C29—H29C	0.9800
C15—C16	1.386 (3)
C1—N1—N2	112.33 (12)	C12—C17—C16	119.86 (18)
C1—N1—C5	128.77 (15)	C12—C17—H17A	120.1
N2—N1—C5	118.88 (14)	C16—C17—H17A	120.1
C3—N2—N1	106.26 (13)	C19—C18—C23	122.60 (14)
C11—N3—C18	127.16 (14)	C19—C18—N3	119.03 (14)
C11—N3—H3A	111.2 (18)	C23—C18—N3	118.19 (14)
C18—N3—H3A	120.9 (19)	C20—C19—C18	117.23 (15)
O—C1—N1	126.87 (14)	C20—C19—C24	121.14 (15)
O—C1—C2	128.80 (15)	C18—C19—C24	121.40 (14)
N1—C1—C2	104.32 (14)	C21—C20—C19	121.27 (15)
C11—C2—C3	133.22 (15)	C21—C20—H20A	119.4
C11—C2—C1	121.61 (16)	C19—C20—H20A	119.4
C3—C2—C1	105.06 (14)	C22—C21—C20	120.15 (15)
N2—C3—C2	112.00 (15)	C22—C21—H21A	119.9
N2—C3—C4	119.07 (16)	C20—C21—H21A	119.9
C2—C3—C4	128.76 (15)	C21—C22—C23	120.86 (15)
C3—C4—H4A	109.5	C21—C22—H22A	119.6
C3—C4—H4B	109.5	C23—C22—H22A	119.6
H4A—C4—H4B	109.5	C22—C23—C18	117.87 (15)
C3—C4—H4C	109.5	C22—C23—C27	121.38 (15)
H4A—C4—H4C	109.5	C18—C23—C27	120.71 (14)
H4B—C4—H4C	109.5	C19—C24—C25	109.39 (14)
C6—C5—C10	120.58 (15)	C19—C24—C26	113.12 (15)
C6—C5—N1	120.37 (15)	C25—C24—C26	111.28 (15)
C10—C5—N1	119.05 (16)	C19—C24—H24A	107.6
C5—C6—C7	119.29 (17)	C25—C24—H24A	107.6
C5—C6—H6A	120.4	C26—C24—H24A	107.6
C7—C6—H6A	120.4	C24—C25—H25A	109.5
C8—C7—C6	120.51 (19)	C24—C25—H25B	109.5
C8—C7—H7A	119.7	H25A—C25—H25B	109.5
C6—C7—H7A	119.7	C24—C25—H25C	109.5
C9—C8—C7	119.53 (16)	H25A—C25—H25C	109.5
C9—C8—H8A	120.2	H25B—C25—H25C	109.5
C7—C8—H8A	120.2	C24—C26—H26A	109.5
C8—C9—C10	120.80 (17)	C24—C26—H26B	109.5
C8—C9—H9A	119.6	H26A—C26—H26B	109.5
C10—C9—H9A	119.6	C24—C26—H26C	109.5
C9—C10—C5	119.27 (18)	H26A—C26—H26C	109.5
C9—C10—H10A	120.4	H26B—C26—H26C	109.5
C5—C10—H10A	120.4	C28—C27—C23	109.70 (16)
N3—C11—C2	118.31 (14)	C28—C27—C29	110.5 (2)
N3—C11—C12	119.19 (14)	C23—C27—C29	113.57 (16)
C2—C11—C12	122.46 (15)	C28—C27—H27A	107.6
C13—C12—C17	119.56 (15)	C23—C27—H27A	107.6
C13—C12—C11	120.92 (14)	C29—C27—H27A	107.6
C17—C12—C11	119.49 (15)	C27—C28—H28A	109.5
C12—C13—C14	120.14 (17)	C27—C28—H28B	109.5
C12—C13—H13A	119.9	H28A—C28—H28B	109.5
C14—C13—H13A	119.9	C27—C28—H28C	109.5
C15—C14—C13	120.07 (19)	H28A—C28—H28C	109.5
C15—C14—H14A	120.0	H28B—C28—H28C	109.5
C13—C14—H14A	120.0	C27—C29—H29A	109.5
C14—C15—C16	120.14 (17)	C27—C29—H29B	109.5
C14—C15—H15A	119.9	H29A—C29—H29B	109.5
C16—C15—H15A	119.9	C27—C29—H29C	109.5
C15—C16—C17	120.22 (18)	H29A—C29—H29C	109.5
C15—C16—H16A	119.9	H29B—C29—H29C	109.5
C17—C16—H16A	119.9
C1—N1—N2—C3	0.44 (16)	C2—C11—C12—C13	66.2 (2)
C5—N1—N2—C3	179.29 (13)	N3—C11—C12—C17	65.8 (2)
N2—N1—C1—O	−178.34 (15)	C2—C11—C12—C17	−111.77 (19)
C5—N1—C1—O	2.9 (2)	C17—C12—C13—C14	0.8 (3)
N2—N1—C1—C2	0.69 (15)	C11—C12—C13—C14	−177.13 (17)
C5—N1—C1—C2	−178.02 (13)	C12—C13—C14—C15	0.1 (3)
O—C1—C2—C11	0.8 (2)	C13—C14—C15—C16	−0.4 (3)
N1—C1—C2—C11	−178.21 (14)	C14—C15—C16—C17	−0.3 (3)
O—C1—C2—C3	177.56 (16)	C13—C12—C17—C16	−1.5 (3)
N1—C1—C2—C3	−1.45 (16)	C11—C12—C17—C16	176.53 (18)
N1—N2—C3—C2	−1.44 (17)	C15—C16—C17—C12	1.2 (3)
N1—N2—C3—C4	174.25 (14)	C11—N3—C18—C19	72.6 (2)
C11—C2—C3—N2	178.08 (16)	C11—N3—C18—C23	−112.15 (18)
C1—C2—C3—N2	1.86 (18)	C23—C18—C19—C20	1.2 (2)
C11—C2—C3—C4	2.9 (3)	N3—C18—C19—C20	176.16 (14)
C1—C2—C3—C4	−173.31 (15)	C23—C18—C19—C24	−173.31 (14)
C1—N1—C5—C6	−21.9 (2)	N3—C18—C19—C24	1.7 (2)
N2—N1—C5—C6	159.49 (14)	C18—C19—C20—C21	−1.2 (2)
C1—N1—C5—C10	158.71 (16)	C24—C19—C20—C21	173.28 (14)
N2—N1—C5—C10	−19.9 (2)	C19—C20—C21—C22	0.5 (2)
C10—C5—C6—C7	0.7 (3)	C20—C21—C22—C23	0.4 (2)
N1—C5—C6—C7	−178.67 (15)	C21—C22—C23—C18	−0.4 (2)
C5—C6—C7—C8	0.5 (3)	C21—C22—C23—C27	−178.27 (15)
C6—C7—C8—C9	−1.4 (3)	C19—C18—C23—C22	−0.4 (2)
C7—C8—C9—C10	1.2 (3)	N3—C18—C23—C22	−175.40 (14)
C8—C9—C10—C5	0.0 (3)	C19—C18—C23—C27	177.48 (15)
C6—C5—C10—C9	−1.0 (2)	N3—C18—C23—C27	2.5 (2)
N1—C5—C10—C9	178.42 (15)	C20—C19—C24—C25	−90.19 (18)
C18—N3—C11—C2	−170.51 (14)	C18—C19—C24—C25	84.08 (19)
C18—N3—C11—C12	11.8 (2)	C20—C19—C24—C26	34.5 (2)
C3—C2—C11—N3	−173.95 (17)	C18—C19—C24—C26	−151.26 (16)
C1—C2—C11—N3	1.8 (2)	C22—C23—C27—C28	89.8 (2)
C3—C2—C11—C12	3.7 (3)	C18—C23—C27—C28	−88.0 (2)
C1—C2—C11—C12	179.36 (13)	C22—C23—C27—C29	−34.4 (2)
N3—C11—C12—C13	−116.23 (18)	C18—C23—C27—C29	147.85 (19)

Cg1 and Cg2 are the centroids of the C18–C23 and N1,N2,C1–C3 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O	0.80 (2)	1.95 (2)	2.6734 (17)	149 (3)
C9—H9A···Cg1i	0.95	2.73	3.601 (2)	153
C14—H14A···Cg2ii	0.96	2.76	3.467 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C18–C23 and N1,N2,C1–C3 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O	0.80 (2)	1.95 (2)	2.6734 (17)	149 (3)
C9—H9A⋯Cg1i	0.95	2.73	3.601 (2)	153
C14—H14A⋯Cg2ii	0.96	2.76	3.467 (2)	132

Symmetry codes: (i) ; (ii) .