4-Methyl-5-phenyl-1H-pyrazol-3-ol

The title compound, C₁₀H₁₀N₂O, crystallizes with two independent mol­ecules in the asymmetric unit, having closely comparable geometries. The dihedral angles between the 1H-pyrazole and benzene rings in the two mol­ecules are 39.57 (14) and 41.95 (13)°. The two mol­ecules are each connected to neighbouring mol­ecules by pairs of inter­molecular O—H...N hydrogen bonds, forming dimers with R₂²(8) ring motifs. These dimers are further linked into R₄⁴(10) ring motifs by inter­molecular N—H...O hydrogen bonds, forming chains along [101]. The crystal structure is further stabilized by a C—H...π inter­action.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.059
• wR factor = 0.204
• Data-to-parameter ratio = 21.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C2A
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         31
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          6

Alert level G
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety       C10B
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         14

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Pyrazolone derivatives have a broad spectrum of biological activities being used as analgesic, antipyretic and anti-inflammatory therapeutical drugs (Brogden, 1986; Gursoy et al., 2000). A class of new compounds with the pyrazolone moiety was synthesized and reported for their antibacterial and antifungal activities by Ragavan et al. (2009, 2010). A new pyrazolone derivative, edaravone (3-methyl-1-phenyl-2-pyrazoline-5-one), is being used as a drug in clinical practice for brain ischemia (Watanabe et al., 1984; Kawai et al., 1997) and the same has been found to be effective against myocardial ischemia (Wu et al., 2002).

There are two independent molecules (A and B) in the asymmetric unit (Fig. 1). The maximum deviations in 1H-pyrazole ring (N1/N2/C7–C9) for molecules A and B are 0.006 (2) and 0.011 (2) Å, respectively, at atoms C6A and C6B. The dihedral angles formed between the 1H-pyrazole ring and benzene ring in molecules A and B are 39.57 (14) and 41.95 (13)°, respectively. The bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to those closely related structures (Shahani et al., 2009, 2010a–c).

In the crystal packing (Fig. 2), pairs of intermolecular O1A—H1OA···N2A and O1B—H1OB···N2B hydrogen bonds (Table 1) form dimers with neighbouring molecules, generating R₂²(8) ring motifs (Bernstein et al., 1995). These dimers are further linked into R₄⁴(10) ring motifs by additional intermolecular N1A—H1NA···O1B and N1B—H1NB···O1A hydrogen bonds (Table 1), forming one dimensional chains along the [101] direction. The crystal structure is further stabilized by C—H···π interaction (Table 1), involving the C1B—C6B benzene ring (centroid Cg1).

Related literature

For background to the biological activity of 4-methyl-3-phenyl-1H-pyrazol-5-ol, see: Brogden (1986); Gursoy et al. (2000); Ragavan et al. (2009, 2010); Watanabe et al. (1984); Kawai et al. (1997); Wu et al. (2002). For related structures, see: Shahani et al. (2009, 2010a,b,c). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

S2. Experimental

The compound 4-methyl-5-phenyl-1-H-pyrazol-3-ol has been synthesized using the method available in the literature (Ragavan et al., 2009, 2010) and recrystallized using the ethanol (white solid). m.p. 278.5–493 K.

S3. Refinement

The H atoms bound to O atoms were located in a difference map and constrained to ride with their parent atoms, with U_iso(H) = 1.5U_eq(O) (O—H = 0.83 Å). The H atoms bound to N atoms were located in a difference map and were refined freely [refined N—H lengths, 1.00 (3) and 0.97 (2) Å]. All other H atoms were positioned geometrically (C—H = 0.93–0.96 Å], with U_iso(H) = 1.2 or 1.5U_eq(C).

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures

	Fig. 1. The molecular structure of the title compound, showing 20% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed approximately along the b axis, showing a one-dimensional chain.

4-Methyl-5-phenyl-1H-pyrazol-3-ol

Crystal data

C10H10N2O	F(000) = 1472
Mr = 174.20	Dx = 1.278 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3052 reflections
a = 26.4082 (19) Å	θ = 3.3–27.2°
b = 11.0972 (8) Å	µ = 0.09 mm^−1
c = 14.1245 (10) Å	T = 100 K
β = 118.996 (1)°	Block, colourless
V = 3620.4 (4) Å^3	0.35 × 0.14 × 0.08 mm
Z = 16

Data collection

Bruker APEXII DUO CCD area-detector diffractometer	5255 independent reflections
Radiation source: fine-focus sealed tube	2907 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ϕ and ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −37→28
Tmin = 0.970, Tmax = 0.993	k = −15→13
19166 measured reflections	l = −19→19

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.204	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0985P)^2] where P = (Fo^2 + 2Fc^2)/3
5255 reflections	(Δ/σ)max = 0.001
243 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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.

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

	x	y	z	Uiso*/Ueq
O1A	0.30484 (5)	1.15234 (15)	0.48624 (10)	0.0513 (4)
H1OA	0.3021	1.1865	0.5356	0.077*
N1A	0.17011 (7)	1.19165 (16)	0.26752 (12)	0.0419 (4)
N2A	0.21137 (6)	1.22060 (17)	0.36985 (11)	0.0416 (4)
C1A	0.09436 (9)	1.0463 (3)	0.07114 (18)	0.0643 (7)
H1AA	0.0772	1.0599	0.1142	0.077*
C2A	0.06077 (11)	1.0113 (3)	−0.0353 (2)	0.0835 (10)
H2AA	0.0211	1.0019	−0.0634	0.100*
C3A	0.08503 (12)	0.9902 (3)	−0.09985 (19)	0.0704 (8)
H3AA	0.0621	0.9665	−0.1715	0.084*
C4A	0.14342 (12)	1.0042 (3)	−0.05821 (19)	0.0676 (7)
H4AA	0.1603	0.9906	−0.1017	0.081*
C5A	0.17726 (10)	1.0384 (3)	0.04793 (17)	0.0605 (6)
H5AA	0.2170	1.0462	0.0758	0.073*
C6A	0.15335 (8)	1.06126 (19)	0.11381 (14)	0.0412 (4)
C7A	0.18926 (8)	1.10453 (19)	0.22525 (14)	0.0386 (4)
C8A	0.24504 (8)	1.07398 (19)	0.30334 (14)	0.0406 (4)
C9A	0.25656 (7)	1.1493 (2)	0.39179 (14)	0.0404 (4)
C10A	0.28424 (9)	0.9785 (2)	0.30003 (17)	0.0526 (5)
H10A	0.2662	0.9409	0.2300	0.079*
H10B	0.2914	0.9190	0.3545	0.079*
H10C	0.3202	1.0143	0.3135	0.079*
O1B	−0.05992 (5)	0.70768 (16)	−0.21038 (10)	0.0515 (4)
H1OB	−0.0528	0.7049	−0.2616	0.077*
N1B	0.08261 (7)	0.69465 (18)	−0.01528 (12)	0.0468 (4)
N2B	0.04080 (6)	0.70277 (17)	−0.12057 (12)	0.0455 (4)
C1B	0.14424 (9)	0.7478 (2)	0.21872 (16)	0.0564 (6)
H1BA	0.1524	0.8034	0.1787	0.068*
C2B	0.17998 (11)	0.7390 (3)	0.32909 (18)	0.0725 (8)
H2BA	0.2123	0.7887	0.3631	0.087*
C3B	0.16837 (12)	0.6580 (3)	0.38904 (18)	0.0708 (8)
H3BA	0.1925	0.6531	0.4635	0.085*
C4B	0.12108 (10)	0.5843 (3)	0.33917 (17)	0.0630 (7)
H4BA	0.1134	0.5285	0.3797	0.076*
C5B	0.08471 (9)	0.5923 (2)	0.22872 (16)	0.0520 (5)
H5BA	0.0524	0.5426	0.1954	0.062*
C6B	0.09620 (8)	0.67397 (19)	0.16757 (14)	0.0409 (4)
C7B	0.05896 (8)	0.68061 (19)	0.04958 (14)	0.0400 (4)
C8B	−0.00068 (8)	0.6800 (2)	−0.01460 (14)	0.0411 (5)
C9B	−0.00976 (8)	0.69654 (19)	−0.12047 (14)	0.0406 (4)
C10B	−0.04620 (9)	0.6615 (3)	0.01754 (18)	0.0598 (6)
H10D	−0.0283	0.6528	0.0947	0.090*
H10E	−0.0679	0.5901	−0.0167	0.090*
H10F	−0.0717	0.7298	−0.0047	0.090*
H1NB	0.1235 (11)	0.687 (3)	0.0001 (19)	0.073 (8)*
H1NA	0.1316 (11)	1.224 (2)	0.2420 (18)	0.064 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0298 (6)	0.0806 (12)	0.0370 (7)	0.0088 (6)	0.0112 (5)	−0.0066 (7)
N1A	0.0321 (7)	0.0554 (11)	0.0348 (7)	0.0049 (7)	0.0134 (6)	−0.0018 (7)
N2A	0.0299 (7)	0.0569 (11)	0.0336 (7)	0.0034 (7)	0.0120 (6)	−0.0038 (7)
C1A	0.0429 (11)	0.093 (2)	0.0548 (12)	−0.0142 (12)	0.0221 (10)	−0.0223 (12)
C2A	0.0463 (13)	0.126 (3)	0.0661 (15)	−0.0210 (15)	0.0174 (12)	−0.0364 (17)
C3A	0.0739 (17)	0.079 (2)	0.0488 (12)	−0.0139 (14)	0.0223 (12)	−0.0220 (12)
C4A	0.0755 (16)	0.082 (2)	0.0516 (12)	−0.0043 (14)	0.0357 (12)	−0.0183 (12)
C5A	0.0478 (11)	0.0854 (19)	0.0496 (11)	−0.0037 (12)	0.0245 (10)	−0.0106 (12)
C6A	0.0393 (9)	0.0436 (12)	0.0394 (9)	−0.0020 (8)	0.0180 (8)	−0.0021 (8)
C7A	0.0342 (8)	0.0461 (12)	0.0385 (9)	−0.0015 (8)	0.0199 (7)	−0.0007 (8)
C8A	0.0330 (8)	0.0515 (13)	0.0383 (9)	0.0012 (8)	0.0181 (7)	−0.0002 (8)
C9A	0.0295 (8)	0.0549 (13)	0.0363 (9)	0.0031 (8)	0.0157 (7)	0.0020 (8)
C10A	0.0426 (10)	0.0601 (15)	0.0530 (11)	0.0109 (10)	0.0214 (9)	−0.0005 (10)
O1B	0.0298 (6)	0.0862 (12)	0.0357 (7)	0.0068 (7)	0.0135 (6)	−0.0007 (6)
N1B	0.0305 (8)	0.0740 (14)	0.0338 (7)	−0.0012 (8)	0.0139 (6)	0.0038 (7)
N2B	0.0291 (7)	0.0713 (13)	0.0316 (7)	0.0007 (7)	0.0113 (6)	0.0029 (7)
C1B	0.0556 (12)	0.0620 (16)	0.0418 (10)	−0.0101 (11)	0.0160 (9)	0.0013 (10)
C2B	0.0650 (15)	0.088 (2)	0.0436 (12)	−0.0171 (14)	0.0097 (11)	−0.0075 (12)
C3B	0.0685 (16)	0.102 (2)	0.0352 (10)	0.0073 (15)	0.0196 (11)	0.0036 (12)
C4B	0.0648 (14)	0.0853 (19)	0.0455 (11)	0.0113 (13)	0.0320 (11)	0.0194 (11)
C5B	0.0494 (11)	0.0626 (15)	0.0466 (10)	0.0015 (10)	0.0253 (9)	0.0098 (10)
C6B	0.0398 (9)	0.0474 (12)	0.0349 (8)	0.0043 (8)	0.0176 (8)	0.0034 (8)
C7B	0.0369 (9)	0.0481 (12)	0.0351 (9)	−0.0006 (8)	0.0174 (8)	0.0021 (8)
C8B	0.0338 (9)	0.0519 (13)	0.0384 (9)	−0.0004 (8)	0.0180 (8)	0.0009 (8)
C9B	0.0308 (8)	0.0524 (13)	0.0363 (9)	0.0002 (8)	0.0145 (7)	−0.0011 (8)
C10B	0.0405 (11)	0.0886 (19)	0.0561 (12)	0.0052 (11)	0.0280 (10)	0.0070 (12)

Geometric parameters (Å, º)

O1A—C9A	1.326 (2)	O1B—C9B	1.323 (2)
O1A—H1OA	0.8273	O1B—H1OB	0.8317
N1A—C7A	1.356 (3)	N1B—C7B	1.345 (2)
N1A—N2A	1.3612 (19)	N1B—N2B	1.359 (2)
N1A—H1NA	0.97 (2)	N1B—H1NB	1.00 (3)
N2A—C9A	1.337 (2)	N2B—C9B	1.338 (2)
C1A—C2A	1.380 (3)	C1B—C2B	1.380 (3)
C1A—C6A	1.381 (3)	C1B—C6B	1.384 (3)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.365 (4)	C2B—C3B	1.368 (4)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.367 (4)	C3B—C4B	1.368 (4)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.375 (3)	C4B—C5B	1.383 (3)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.378 (3)	C5B—C6B	1.383 (3)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.470 (2)	C6B—C7B	1.470 (2)
C7A—C8A	1.388 (2)	C7B—C8B	1.385 (2)
C8A—C9A	1.409 (3)	C8B—C9B	1.407 (3)
C8A—C10A	1.498 (3)	C8B—C10B	1.491 (3)
C10A—H10A	0.9600	C10B—H10D	0.9600
C10A—H10B	0.9600	C10B—H10E	0.9600
C10A—H10C	0.9600	C10B—H10F	0.9600
C9A—O1A—H1OA	115.1	C9B—O1B—H1OB	106.7
C7A—N1A—N2A	111.00 (15)	C7B—N1B—N2B	110.74 (15)
C7A—N1A—H1NA	130.4 (15)	C7B—N1B—H1NB	130.8 (14)
N2A—N1A—H1NA	117.7 (14)	N2B—N1B—H1NB	117.7 (14)
C9A—N2A—N1A	105.76 (15)	C9B—N2B—N1B	106.09 (15)
C2A—C1A—C6A	120.2 (2)	C2B—C1B—C6B	120.0 (2)
C2A—C1A—H1AA	119.9	C2B—C1B—H1BA	120.0
C6A—C1A—H1AA	119.9	C6B—C1B—H1BA	120.0
C3A—C2A—C1A	120.9 (2)	C3B—C2B—C1B	120.7 (2)
C3A—C2A—H2AA	119.5	C3B—C2B—H2BA	119.7
C1A—C2A—H2AA	119.5	C1B—C2B—H2BA	119.7
C2A—C3A—C4A	119.3 (2)	C4B—C3B—C2B	119.8 (2)
C2A—C3A—H3AA	120.3	C4B—C3B—H3BA	120.1
C4A—C3A—H3AA	120.3	C2B—C3B—H3BA	120.1
C3A—C4A—C5A	120.1 (2)	C3B—C4B—C5B	120.2 (2)
C3A—C4A—H4AA	119.9	C3B—C4B—H4BA	119.9
C5A—C4A—H4AA	119.9	C5B—C4B—H4BA	119.9
C4A—C5A—C6A	121.3 (2)	C4B—C5B—C6B	120.3 (2)
C4A—C5A—H5AA	119.4	C4B—C5B—H5BA	119.9
C6A—C5A—H5AA	119.4	C6B—C5B—H5BA	119.9
C5A—C6A—C1A	118.19 (18)	C1B—C6B—C5B	119.03 (18)
C5A—C6A—C7A	120.97 (18)	C1B—C6B—C7B	120.16 (18)
C1A—C6A—C7A	120.81 (18)	C5B—C6B—C7B	120.79 (18)
N1A—C7A—C8A	107.63 (16)	N1B—C7B—C8B	108.12 (15)
N1A—C7A—C6A	121.31 (16)	N1B—C7B—C6B	120.11 (16)
C8A—C7A—C6A	131.04 (18)	C8B—C7B—C6B	131.71 (17)
C7A—C8A—C9A	104.45 (17)	C7B—C8B—C9B	104.41 (16)
C7A—C8A—C10A	129.14 (17)	C7B—C8B—C10B	129.08 (17)
C9A—C8A—C10A	126.32 (17)	C9B—C8B—C10B	126.47 (17)
O1A—C9A—N2A	122.24 (17)	O1B—C9B—N2B	121.95 (16)
O1A—C9A—C8A	126.60 (17)	O1B—C9B—C8B	127.43 (17)
N2A—C9A—C8A	111.16 (15)	N2B—C9B—C8B	110.60 (15)
C8A—C10A—H10A	109.5	C8B—C10B—H10D	109.5
C8A—C10A—H10B	109.5	C8B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
C8A—C10A—H10C	109.5	C8B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
C7A—N1A—N2A—C9A	−0.7 (2)	C7B—N1B—N2B—C9B	1.5 (2)
C6A—C1A—C2A—C3A	0.3 (5)	C6B—C1B—C2B—C3B	−0.2 (4)
C1A—C2A—C3A—C4A	0.0 (5)	C1B—C2B—C3B—C4B	0.4 (5)
C2A—C3A—C4A—C5A	0.4 (5)	C2B—C3B—C4B—C5B	−0.7 (4)
C3A—C4A—C5A—C6A	−1.2 (4)	C3B—C4B—C5B—C6B	0.8 (4)
C4A—C5A—C6A—C1A	1.4 (4)	C2B—C1B—C6B—C5B	0.2 (4)
C4A—C5A—C6A—C7A	−176.4 (2)	C2B—C1B—C6B—C7B	−178.2 (2)
C2A—C1A—C6A—C5A	−1.0 (4)	C4B—C5B—C6B—C1B	−0.5 (3)
C2A—C1A—C6A—C7A	176.8 (3)	C4B—C5B—C6B—C7B	178.0 (2)
N2A—N1A—C7A—C8A	0.7 (2)	N2B—N1B—C7B—C8B	−0.3 (2)
N2A—N1A—C7A—C6A	−177.51 (17)	N2B—N1B—C7B—C6B	−177.91 (18)
C5A—C6A—C7A—N1A	138.9 (2)	C1B—C6B—C7B—N1B	39.6 (3)
C1A—C6A—C7A—N1A	−38.9 (3)	C5B—C6B—C7B—N1B	−138.8 (2)
C5A—C6A—C7A—C8A	−38.9 (3)	C1B—C6B—C7B—C8B	−137.3 (2)
C1A—C6A—C7A—C8A	143.3 (2)	C5B—C6B—C7B—C8B	44.2 (3)
N1A—C7A—C8A—C9A	−0.5 (2)	N1B—C7B—C8B—C9B	−0.9 (2)
C6A—C7A—C8A—C9A	177.5 (2)	C6B—C7B—C8B—C9B	176.3 (2)
N1A—C7A—C8A—C10A	176.4 (2)	N1B—C7B—C8B—C10B	177.0 (2)
C6A—C7A—C8A—C10A	−5.6 (4)	C6B—C7B—C8B—C10B	−5.9 (4)
N1A—N2A—C9A—O1A	−179.23 (17)	N1B—N2B—C9B—O1B	176.63 (19)
N1A—N2A—C9A—C8A	0.4 (2)	N1B—N2B—C9B—C8B	−2.1 (2)
C7A—C8A—C9A—O1A	179.64 (19)	C7B—C8B—C9B—O1B	−176.7 (2)
C10A—C8A—C9A—O1A	2.7 (3)	C10B—C8B—C9B—O1B	5.3 (4)
C7A—C8A—C9A—N2A	0.1 (2)	C7B—C8B—C9B—N2B	1.9 (2)
C10A—C8A—C9A—N2A	−176.89 (19)	C10B—C8B—C9B—N2B	−176.1 (2)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C1B–C6B benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···N2A^i	0.83	1.85	2.673 (2)	171
O1B—H1OB···N2B^ii	0.83	1.84	2.670 (2)	177
N1B—H1NB···O1A^iii	1.00 (3)	1.85 (3)	2.836 (3)	171 (3)
N1A—H1NA···O1B^iv	0.97 (3)	1.88 (3)	2.844 (2)	173 (2)
C10A—H10C···Cg1^v	0.96	2.77	3.575 (3)	142

Symmetry codes: (i) −x+1/2, −y+5/2, −z+1; (ii) −x, y, −z−1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x, −y+2, −z; (v) x, −y, z−1/2.