5-Ethyl-4-phenyl-1H-pyrazol-3(2H)-one.

The asymmetric unit of the title compound, C(11)H(12)N(2)O, consists of two crystallographically independent mol-ecules (A and B) with similar geometries. Both mol-ecules exist in a keto form, the C=O bond length being 1.286 (2) Å in A and 1.283 (2) Å in B. The dihedral angles between the pyrazole ring and the attached phenyl ring are 43.28 (12) and 46.88 (11)°, respectively, for A and B. The ethyl unit in mol-ecule B is disordered over two positions with a site-occupancy ratio of 0.508 (5):0.492 (5). In the crystal, each of the independent mol-ecules forms a centrosymmetric dimer with an R(2) (2)(8) ring motif through a pair of N-H⋯O hydrogen bonds. These dimers are further connected into a three-dimensional network by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds. Inter-molecular C-H⋯π inter-actions are also present.

Related literature

For background to pyrazole derivatives and their microbial activity, see: Ragavan et al. (2009 ▶, 2010 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Loh et al. (2010 ▶, 2010a ▶,b ▶, 2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C11H12N2O

M = 188.23

Monoclinic,

a = 11.0898 (3) Å

b = 13.2171 (4) Å

c = 15.0265 (5) Å

β = 114.539 (2)°

V = 2003.58 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.60 × 0.16 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.953, T max = 0.989

22130 measured reflections

5845 independent reflections

3654 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.166

S = 1.05

5845 reflections

284 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001589/is2655sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001589/is2655Isup2.hkl

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

C11H12N2O	F(000) = 800
Mr = 188.23	Dx = 1.248 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4628 reflections
a = 11.0898 (3) Å	θ = 2.5–30.0°
b = 13.2171 (4) Å	µ = 0.08 mm−1
c = 15.0265 (5) Å	T = 100 K
β = 114.539 (2)°	Needle, colourless
V = 2003.58 (11) Å3	0.60 × 0.16 × 0.13 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	5845 independent reflections
Radiation source: fine-focus sealed tube	3654 reflections with I > 2σ(I)
graphite	Rint = 0.063
φ and ω scans	θmax = 30.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.953, Tmax = 0.989	k = −18→18
22130 measured reflections	l = −20→21

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)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.166	w = 1/[σ2(Fo2) + (0.0659P)2 + 0.5295P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
5845 reflections	Δρmax = 0.38 e Å−3
284 parameters	Δρmin = −0.30 e Å−3
2 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0163 (19)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	Occ. (<1)
O1A	0.59450 (13)	0.07629 (9)	0.94578 (11)	0.0314 (3)
N1A	0.29084 (17)	0.16378 (11)	0.92423 (13)	0.0288 (4)
N2A	0.38633 (15)	0.09048 (11)	0.94491 (12)	0.0271 (4)
C1A	0.32664 (18)	0.24453 (13)	0.88567 (14)	0.0246 (4)
C2A	0.48806 (18)	0.12736 (13)	0.92718 (14)	0.0244 (4)
C3A	0.44982 (17)	0.22608 (12)	0.88657 (14)	0.0239 (4)
C4A	0.53044 (18)	0.29233 (13)	0.85342 (16)	0.0298 (4)
C5A	0.6668 (2)	0.30005 (15)	0.90864 (18)	0.0396 (5)
H5AA	0.7066	0.2645	0.9671	0.047*
C6A	0.7438 (2)	0.36080 (18)	0.8767 (3)	0.0602 (8)
H6AA	0.8348	0.3652	0.9137	0.072*
C7A	0.6861 (3)	0.41400 (18)	0.7910 (3)	0.0685 (10)
H7AA	0.7379	0.4549	0.7704	0.082*
C8A	0.5513 (3)	0.40705 (19)	0.7351 (2)	0.0604 (8)
H8AA	0.5124	0.4430	0.6768	0.072*
C9A	0.4736 (2)	0.34624 (16)	0.76586 (18)	0.0401 (5)
H9AA	0.3829	0.3415	0.7278	0.048*
C10A	0.23852 (19)	0.33569 (14)	0.85216 (16)	0.0306 (4)
H10C	0.1769	0.3258	0.7845	0.037*
H10D	0.2927	0.3942	0.8546	0.037*
C11A	0.1600 (2)	0.35798 (17)	0.91215 (19)	0.0450 (6)
H11D	0.1092	0.4187	0.8884	0.068*
H11E	0.2199	0.3668	0.9795	0.068*
H11F	0.1013	0.3025	0.9064	0.068*
O1B	1.07863 (12)	0.06616 (9)	0.92558 (9)	0.0254 (3)
N1B	0.73764 (15)	0.06391 (11)	0.83821 (12)	0.0275 (4)
N2B	0.86312 (14)	0.04445 (11)	0.90754 (12)	0.0228 (3)
C1B	0.74826 (19)	0.11417 (14)	0.76342 (15)	0.0303 (4)
C2B	0.95360 (17)	0.07674 (12)	0.87492 (13)	0.0215 (4)
C3B	0.88097 (18)	0.12138 (13)	0.78120 (14)	0.0251 (4)
C4B	0.9388 (2)	0.16679 (13)	0.71837 (14)	0.0291 (4)
C5B	1.0386 (2)	0.11721 (15)	0.70194 (16)	0.0361 (5)
H5BA	1.0694	0.0549	0.7315	0.043*
C6B	1.0928 (3)	0.15955 (16)	0.64204 (18)	0.0505 (7)
H6BA	1.1588	0.1253	0.6312	0.061*
C7B	1.0483 (3)	0.25308 (17)	0.59830 (17)	0.0541 (7)
H7BA	1.0840	0.2814	0.5579	0.065*
C8B	0.9506 (3)	0.30381 (16)	0.61513 (16)	0.0459 (6)
H8BA	0.9209	0.3665	0.5862	0.055*
C9B	0.8973 (2)	0.26163 (15)	0.67475 (15)	0.0360 (5)
H9BA	0.8326	0.2969	0.6862	0.043*
C10B	0.6280 (2)	0.14952 (18)	0.67717 (18)	0.0499 (6)
H10A	0.5568	0.1581	0.6980	0.060*	0.508 (5)
H10B	0.6473	0.2157	0.6583	0.060*	0.508 (5)
H10E	0.6172	0.2209	0.6868	0.060*	0.492 (5)
H10F	0.6477	0.1442	0.6202	0.060*	0.492 (5)
C11B	0.5811 (4)	0.0874 (3)	0.5935 (3)	0.0427 (13)	0.508 (5)
H11A	0.5027	0.1168	0.5442	0.064*	0.508 (5)
H11B	0.5608	0.0215	0.6104	0.064*	0.508 (5)
H11C	0.6481	0.0816	0.5689	0.064*	0.508 (5)
C11C	0.5046 (3)	0.1031 (3)	0.6533 (4)	0.0395 (13)	0.492 (5)
H11G	0.4387	0.1358	0.5970	0.059*	0.492 (5)
H11H	0.4805	0.1090	0.7075	0.059*	0.492 (5)
H11I	0.5101	0.0329	0.6390	0.059*	0.492 (5)
H1NB	0.669 (2)	0.0719 (16)	0.8648 (17)	0.043 (6)*
H2NB	0.881 (2)	0.0033 (18)	0.9694 (18)	0.053 (7)*
H2NA	0.384 (2)	0.029 (2)	0.9802 (19)	0.060 (8)*
H1NA	0.204 (3)	0.1404 (18)	0.9184 (19)	0.052 (7)*

	U11	U22	U33	U12	U13	U23
O1A	0.0284 (7)	0.0292 (7)	0.0398 (9)	0.0114 (5)	0.0174 (7)	0.0106 (6)
N1A	0.0297 (9)	0.0254 (8)	0.0368 (10)	0.0094 (6)	0.0193 (8)	0.0101 (6)
N2A	0.0286 (8)	0.0247 (8)	0.0325 (9)	0.0087 (6)	0.0172 (7)	0.0083 (6)
C1A	0.0265 (9)	0.0235 (8)	0.0255 (10)	0.0036 (7)	0.0125 (8)	0.0027 (7)
C2A	0.0246 (9)	0.0250 (8)	0.0234 (10)	0.0043 (7)	0.0097 (7)	0.0020 (7)
C3A	0.0234 (9)	0.0223 (8)	0.0256 (10)	0.0022 (6)	0.0097 (7)	0.0024 (7)
C4A	0.0229 (9)	0.0237 (9)	0.0442 (13)	0.0030 (7)	0.0153 (9)	0.0036 (8)
C5A	0.0263 (10)	0.0321 (10)	0.0574 (15)	0.0007 (8)	0.0144 (10)	−0.0018 (10)
C6A	0.0270 (12)	0.0389 (13)	0.116 (3)	−0.0031 (9)	0.0309 (15)	−0.0020 (14)
C7A	0.0510 (16)	0.0381 (13)	0.141 (3)	0.0047 (11)	0.064 (2)	0.0232 (16)
C8A	0.0510 (15)	0.0508 (14)	0.100 (2)	0.0200 (11)	0.0524 (16)	0.0411 (14)
C9A	0.0293 (11)	0.0391 (11)	0.0591 (16)	0.0110 (8)	0.0255 (11)	0.0210 (10)
C10A	0.0316 (10)	0.0290 (9)	0.0372 (12)	0.0101 (7)	0.0203 (9)	0.0095 (8)
C11A	0.0548 (15)	0.0391 (12)	0.0558 (16)	0.0228 (10)	0.0375 (13)	0.0147 (10)
O1B	0.0221 (6)	0.0288 (6)	0.0264 (7)	0.0022 (5)	0.0111 (6)	0.0067 (5)
N1B	0.0201 (8)	0.0305 (8)	0.0294 (9)	0.0028 (6)	0.0076 (7)	0.0030 (6)
N2B	0.0189 (7)	0.0276 (7)	0.0221 (8)	0.0029 (5)	0.0087 (6)	0.0017 (6)
C1B	0.0321 (10)	0.0248 (9)	0.0266 (10)	0.0025 (7)	0.0049 (8)	0.0028 (7)
C2B	0.0249 (9)	0.0212 (8)	0.0217 (9)	0.0026 (6)	0.0129 (7)	0.0004 (6)
C3B	0.0307 (10)	0.0229 (8)	0.0213 (9)	0.0022 (7)	0.0104 (8)	0.0019 (7)
C4B	0.0410 (11)	0.0255 (9)	0.0186 (9)	−0.0031 (7)	0.0102 (8)	0.0008 (7)
C5B	0.0589 (14)	0.0258 (9)	0.0337 (12)	−0.0007 (9)	0.0294 (11)	0.0013 (8)
C6B	0.092 (2)	0.0353 (11)	0.0465 (15)	−0.0071 (11)	0.0504 (15)	−0.0031 (10)
C7B	0.104 (2)	0.0381 (12)	0.0357 (13)	−0.0155 (13)	0.0448 (15)	−0.0001 (10)
C8B	0.0787 (18)	0.0286 (10)	0.0245 (11)	−0.0093 (10)	0.0156 (12)	0.0046 (8)
C9B	0.0488 (13)	0.0281 (10)	0.0239 (10)	−0.0020 (8)	0.0081 (9)	0.0042 (7)
C10B	0.0427 (13)	0.0442 (13)	0.0400 (14)	0.0094 (10)	−0.0054 (11)	0.0093 (10)
C11B	0.032 (2)	0.053 (3)	0.033 (3)	0.0001 (18)	0.0032 (19)	0.0136 (19)
C11C	0.021 (2)	0.047 (3)	0.047 (3)	−0.0040 (17)	0.0109 (19)	0.014 (2)

O1A—C2A	1.286 (2)	N1B—H1NB	1.00 (2)
N1A—C1A	1.350 (2)	N2B—C2B	1.356 (2)
N1A—N2A	1.372 (2)	N2B—H2NB	1.02 (3)
N1A—H1NA	0.98 (2)	C1B—C3B	1.386 (3)
N2A—C2A	1.353 (2)	C1B—C10B	1.497 (3)
N2A—H2NA	0.98 (3)	C2B—C3B	1.427 (2)
C1A—C3A	1.382 (2)	C3B—C4B	1.471 (3)
C1A—C10A	1.500 (2)	C4B—C5B	1.394 (3)
C2A—C3A	1.428 (2)	C4B—C9B	1.401 (3)
C3A—C4A	1.478 (2)	C5B—C6B	1.391 (3)
C4A—C5A	1.394 (3)	C5B—H5BA	0.9300
C4A—C9A	1.396 (3)	C6B—C7B	1.391 (3)
C5A—C6A	1.395 (3)	C6B—H6BA	0.9300
C5A—H5AA	0.9300	C7B—C8B	1.383 (4)
C6A—C7A	1.371 (4)	C7B—H7BA	0.9300
C6A—H6AA	0.9300	C8B—C9B	1.379 (3)
C7A—C8A	1.381 (4)	C8B—H8BA	0.9300
C7A—H7AA	0.9300	C9B—H9BA	0.9300
C8A—C9A	1.391 (3)	C10B—C11C	1.403 (3)
C8A—H8AA	0.9300	C10B—C11B	1.408 (3)
C9A—H9AA	0.9300	C10B—H10A	0.9700
C10A—C11A	1.520 (3)	C10B—H10B	0.9700
C10A—H10C	0.9700	C10B—H10E	0.9700
C10A—H10D	0.9700	C10B—H10F	0.9700
C11A—H11D	0.9600	C11B—H11A	0.9600
C11A—H11E	0.9600	C11B—H11B	0.9600
C11A—H11F	0.9600	C11B—H11C	0.9600
O1B—C2B	1.283 (2)	C11C—H11G	0.9600
N1B—C1B	1.352 (2)	C11C—H11H	0.9600
N1B—N2B	1.372 (2)	C11C—H11I	0.9600
C1A—N1A—N2A	108.56 (15)	N1B—N2B—H2NB	123.0 (14)
C1A—N1A—H1NA	131.6 (14)	N1B—C1B—C3B	109.01 (16)
N2A—N1A—H1NA	115.8 (14)	N1B—C1B—C10B	121.27 (19)
C2A—N2A—N1A	109.22 (15)	C3B—C1B—C10B	129.69 (19)
C2A—N2A—H2NA	128.0 (15)	O1B—C2B—N2B	122.08 (16)
N1A—N2A—H2NA	121.5 (15)	O1B—C2B—C3B	131.19 (16)
N1A—C1A—C3A	108.78 (15)	N2B—C2B—C3B	106.72 (16)
N1A—C1A—C10A	120.80 (16)	C1B—C3B—C2B	106.31 (16)
C3A—C1A—C10A	130.40 (16)	C1B—C3B—C4B	127.96 (17)
O1A—C2A—N2A	122.23 (16)	C2B—C3B—C4B	125.72 (17)
O1A—C2A—C3A	130.95 (17)	C5B—C4B—C9B	117.91 (18)
N2A—C2A—C3A	106.82 (15)	C5B—C4B—C3B	120.77 (16)
C1A—C3A—C2A	106.39 (15)	C9B—C4B—C3B	121.31 (18)
C1A—C3A—C4A	128.76 (15)	C6B—C5B—C4B	120.9 (2)
C2A—C3A—C4A	124.86 (16)	C6B—C5B—H5BA	119.5
C5A—C4A—C9A	118.53 (19)	C4B—C5B—H5BA	119.5
C5A—C4A—C3A	120.08 (18)	C5B—C6B—C7B	120.0 (2)
C9A—C4A—C3A	121.37 (17)	C5B—C6B—H6BA	120.0
C4A—C5A—C6A	120.4 (2)	C7B—C6B—H6BA	120.0
C4A—C5A—H5AA	119.8	C8B—C7B—C6B	119.7 (2)
C6A—C5A—H5AA	119.8	C8B—C7B—H7BA	120.1
C7A—C6A—C5A	120.3 (2)	C6B—C7B—H7BA	120.1
C7A—C6A—H6AA	119.8	C9B—C8B—C7B	120.1 (2)
C5A—C6A—H6AA	119.8	C9B—C8B—H8BA	119.9
C6A—C7A—C8A	120.2 (2)	C7B—C8B—H8BA	119.9
C6A—C7A—H7AA	119.9	C8B—C9B—C4B	121.3 (2)
C8A—C7A—H7AA	119.9	C8B—C9B—H9BA	119.3
C7A—C8A—C9A	120.0 (2)	C4B—C9B—H9BA	119.3
C7A—C8A—H8AA	120.0	C11C—C10B—C1B	120.6 (3)
C9A—C8A—H8AA	120.0	C11B—C10B—C1B	117.2 (2)
C8A—C9A—C4A	120.6 (2)	C11B—C10B—H10A	108.0
C8A—C9A—H9AA	119.7	C1B—C10B—H10A	108.0
C4A—C9A—H9AA	119.7	C11B—C10B—H10B	108.0
C1A—C10A—C11A	114.22 (16)	C1B—C10B—H10B	108.0
C1A—C10A—H10C	108.7	H10A—C10B—H10B	107.2
C11A—C10A—H10C	108.7	C11C—C10B—H10E	107.2
C1A—C10A—H10D	108.7	C1B—C10B—H10E	107.2
C11A—C10A—H10D	108.7	C11C—C10B—H10F	107.2
H10C—C10A—H10D	107.6	C1B—C10B—H10F	107.2
C10A—C11A—H11D	109.5	H10E—C10B—H10F	106.8
C10A—C11A—H11E	109.5	C10B—C11B—H11A	109.5
H11D—C11A—H11E	109.5	C10B—C11B—H11B	109.5
C10A—C11A—H11F	109.5	C10B—C11B—H11C	109.5
H11D—C11A—H11F	109.5	C10B—C11C—H11G	109.5
H11E—C11A—H11F	109.5	C10B—C11C—H11H	109.5
C1B—N1B—N2B	108.18 (15)	H11G—C11C—H11H	109.5
C1B—N1B—H1NB	128.5 (13)	C10B—C11C—H11I	109.5
N2B—N1B—H1NB	114.6 (14)	H11G—C11C—H11I	109.5
C2B—N2B—N1B	109.63 (15)	H11H—C11C—H11I	109.5
C2B—N2B—H2NB	126.9 (14)
C1A—N1A—N2A—C2A	5.0 (2)	N2B—N1B—C1B—C3B	4.0 (2)
N2A—N1A—C1A—C3A	−3.5 (2)	N2B—N1B—C1B—C10B	−177.96 (18)
N2A—N1A—C1A—C10A	177.71 (17)	N1B—N2B—C2B—O1B	−179.06 (15)
N1A—N2A—C2A—O1A	175.93 (17)	N1B—N2B—C2B—C3B	1.65 (18)
N1A—N2A—C2A—C3A	−4.4 (2)	N1B—C1B—C3B—C2B	−2.9 (2)
N1A—C1A—C3A—C2A	0.8 (2)	C10B—C1B—C3B—C2B	179.2 (2)
C10A—C1A—C3A—C2A	179.43 (19)	N1B—C1B—C3B—C4B	177.89 (17)
N1A—C1A—C3A—C4A	−179.05 (19)	C10B—C1B—C3B—C4B	0.1 (3)
C10A—C1A—C3A—C4A	−0.4 (3)	O1B—C2B—C3B—C1B	−178.43 (18)
O1A—C2A—C3A—C1A	−178.1 (2)	N2B—C2B—C3B—C1B	0.77 (19)
N2A—C2A—C3A—C1A	2.2 (2)	O1B—C2B—C3B—C4B	0.8 (3)
O1A—C2A—C3A—C4A	1.7 (3)	N2B—C2B—C3B—C4B	179.96 (16)
N2A—C2A—C3A—C4A	−177.92 (18)	C1B—C3B—C4B—C5B	−134.8 (2)
C1A—C3A—C4A—C5A	138.1 (2)	C2B—C3B—C4B—C5B	46.2 (3)
C2A—C3A—C4A—C5A	−41.7 (3)	C1B—C3B—C4B—C9B	46.4 (3)
C1A—C3A—C4A—C9A	−43.5 (3)	C2B—C3B—C4B—C9B	−132.6 (2)
C2A—C3A—C4A—C9A	136.7 (2)	C9B—C4B—C5B—C6B	−1.6 (3)
C9A—C4A—C5A—C6A	0.2 (3)	C3B—C4B—C5B—C6B	179.5 (2)
C3A—C4A—C5A—C6A	178.6 (2)	C4B—C5B—C6B—C7B	0.6 (4)
C4A—C5A—C6A—C7A	0.4 (4)	C5B—C6B—C7B—C8B	0.4 (4)
C5A—C6A—C7A—C8A	−0.6 (4)	C6B—C7B—C8B—C9B	−0.2 (4)
C6A—C7A—C8A—C9A	0.2 (4)	C7B—C8B—C9B—C4B	−0.8 (3)
C7A—C8A—C9A—C4A	0.4 (4)	C5B—C4B—C9B—C8B	1.8 (3)
C5A—C4A—C9A—C8A	−0.6 (3)	C3B—C4B—C9B—C8B	−179.4 (2)
C3A—C4A—C9A—C8A	−179.0 (2)	N1B—C1B—C10B—C11C	−22.8 (4)
N1A—C1A—C10A—C11A	33.3 (3)	C3B—C1B—C10B—C11C	154.8 (3)
C3A—C1A—C10A—C11A	−145.2 (2)	N1B—C1B—C10B—C11B	−96.9 (3)
C1B—N1B—N2B—C2B	−3.53 (19)	C3B—C1B—C10B—C11B	80.7 (3)

Cg1 and Cg2 are the centroids of the C4B–C9B and C4A–C9A rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1NB···O1A	1.00 (2)	1.73 (2)	2.700 (2)	161 (2)
N2B—H2NB···O1Bi	1.02 (2)	1.72 (2)	2.738 (2)	176 (2)
N2A—H2NA···O1Aii	0.98 (3)	1.74 (3)	2.704 (2)	171 (2)
N1A—H1NA···O1Biii	0.98 (3)	1.74 (3)	2.691 (2)	162 (2)
C8A—H8AA···O1Aiv	0.93	2.47	3.370 (3)	163
C10A—H10C···Cg1iii	0.97	2.61	3.464 (2)	147
C10B—H10E···Cg2	0.97	2.71	3.524 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C4B–C9B and C4A–C9A rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1B—H1NB⋯O1A	1.00 (2)	1.73 (2)	2.700 (2)	161 (2)
N2B—H2NB⋯O1Bi	1.02 (2)	1.72 (2)	2.738 (2)	176 (2)
N2A—H2NA⋯O1Aii	0.98 (3)	1.74 (3)	2.704 (2)	171 (2)
N1A—H1NA⋯O1Biii	0.98 (3)	1.74 (3)	2.691 (2)	162 (2)
C8A—H8AA⋯O1Aiv	0.93	2.47	3.370 (3)	163
C10A—H10C⋯Cg1iii	0.97	2.61	3.464 (2)	147
C10B—H10E⋯Cg2	0.97	2.71	3.524 (3)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .