1-[5-(2-Chloro-phen-yl)-5-hy-droxy-3-methyl-4,5-dihydro-1H-pyrazol-1-yl]-ethanone.

The title compound, C(12)H(13)ClN(2)O(2), crystallizes with two independent but very similar mol-ecules (A and B) in the asymmetric unit. The pyrazole ring in each mol-ecule has an envelope conformation. The dihedral angle between the pyrazole ring mean plane and the benzene ring is 86.07 (14)° in A and 85.99 (14)° in B. In the crystal, the A and B mol-ecules are linked via a pair of O-H⋯O hydrogen bonds, forming dimers. These dimers are further linked via C-H⋯O inter-actions to form -A-B-A-B- chains propagating along the c-axis direction.

Related literature

For the bioactivities of 5-hy­droxy­pyrazolines, see: Sauzem et al. (2008 ▶); Zhao et al. (2009 ▶); Idrees et al. (2009 ▶). For the crystal structures of related 5-hy­droxy­pyrazolines, see: Kargar, Kia, Froozandeh et al. (2011 ▶); Kargar, Kia, Moghadamm et al. (2011 ▶).

Experimental

Crystal data

C12H13ClN2O2

M = 252.70

Monoclinic,

a = 10.320 (3) Å

b = 14.916 (4) Å

c = 16.346 (4) Å

β = 95.158 (3)°

V = 2506.0 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.39 × 0.25 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.893, T max = 0.957

16979 measured reflections

4663 independent reflections

3077 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.159

S = 1.02

4663 reflections

313 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007283/su2378sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007283/su2378Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007283/su2378Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812007283/su2378Isup4.cml

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

C12H13ClN2O2	F(000) = 1056
Mr = 252.70	Dx = 1.340 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3669 reflections
a = 10.320 (3) Å	θ = 2.4–25.9°
b = 14.916 (4) Å	µ = 0.30 mm−1
c = 16.346 (4) Å	T = 296 K
β = 95.158 (3)°	Block, colourless
V = 2506.0 (12) Å3	0.39 × 0.25 × 0.15 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	4663 independent reflections
Radiation source: fine-focus sealed tube	3077 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
phi and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
Tmin = 0.893, Tmax = 0.957	k = −18→18
16979 measured reflections	l = −19→19

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0804P)2 + 0.8196P] where P = (Fo2 + 2Fc2)/3
4663 reflections	(Δ/σ)max = 0.001
313 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.35 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 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
C1	0.5236 (3)	0.2945 (2)	0.27457 (16)	0.0630 (8)
C2	0.6517 (3)	0.32278 (17)	0.26911 (14)	0.0484 (6)
C3	0.6858 (3)	0.40628 (19)	0.30087 (17)	0.0643 (8)
H3	0.7701	0.4272	0.2977	0.077*
C4	0.5966 (5)	0.4597 (2)	0.3375 (2)	0.0904 (12)
H4	0.6214	0.5154	0.3591	0.109*
C5	0.4714 (5)	0.4294 (3)	0.3415 (2)	0.1025 (15)
H5	0.4112	0.4653	0.3650	0.123*
C6	0.4349 (4)	0.3468 (3)	0.3110 (2)	0.0891 (12)
H6	0.3506	0.3261	0.3148	0.107*
C7	0.7497 (2)	0.27082 (16)	0.22292 (14)	0.0427 (6)
C8	0.7104 (2)	0.26559 (16)	0.12996 (14)	0.0452 (6)
H8A	0.6204	0.2833	0.1172	0.054*
H8B	0.7656	0.3035	0.0997	0.054*
C9	0.7293 (2)	0.16951 (17)	0.11060 (15)	0.0470 (6)
C10	0.7195 (3)	0.1336 (2)	0.02506 (16)	0.0630 (8)
H10A	0.7276	0.0695	0.0267	0.094*
H10B	0.7879	0.1585	−0.0040	0.094*
H10C	0.6368	0.1497	−0.0026	0.094*
C11	0.7751 (3)	0.14051 (18)	0.32065 (16)	0.0514 (6)
C12	0.7807 (4)	0.0402 (2)	0.32863 (19)	0.0811 (10)
H12A	0.8560	0.0181	0.3047	0.122*
H12B	0.7038	0.0144	0.3006	0.122*
H12C	0.7857	0.0240	0.3857	0.122*
C13	0.3110 (3)	0.3263 (2)	−0.02266 (16)	0.0621 (8)
C14	0.1813 (3)	0.34881 (17)	−0.01755 (14)	0.0470 (6)
C15	0.1388 (3)	0.43010 (17)	−0.05224 (17)	0.0658 (8)
H15	0.0529	0.4476	−0.0491	0.079*
C16	0.2215 (5)	0.4854 (2)	−0.0913 (2)	0.0941 (13)
H16	0.1904	0.5387	−0.1151	0.113*
C17	0.3479 (5)	0.4620 (3)	−0.0950 (2)	0.1070 (15)
H17	0.4032	0.4998	−0.1207	0.128*
C18	0.3958 (4)	0.3819 (3)	−0.0606 (2)	0.0906 (12)
H18	0.4825	0.3659	−0.0628	0.109*
C19	0.0867 (2)	0.29137 (16)	0.02655 (14)	0.0427 (6)
C20	0.1250 (2)	0.27892 (16)	0.11897 (14)	0.0459 (6)
H20A	0.2142	0.2975	0.1335	0.055*
H20B	0.0680	0.3128	0.1515	0.055*
C21	0.1094 (2)	0.18061 (16)	0.13134 (15)	0.0457 (6)
C22	0.1166 (3)	0.13570 (19)	0.21316 (15)	0.0564 (7)
H22A	0.1115	0.0719	0.2057	0.085*
H22B	0.0455	0.1555	0.2427	0.085*
H22C	0.1974	0.1508	0.2438	0.085*
C23	0.0645 (2)	0.16960 (16)	−0.07964 (15)	0.0455 (6)
C24	0.0633 (3)	0.07144 (18)	−0.09644 (19)	0.0707 (9)
H24A	0.0579	0.0615	−0.1547	0.106*
H24B	−0.0106	0.0447	−0.0742	0.106*
H24C	0.1417	0.0449	−0.0712	0.106*
Cl1	0.46874 (8)	0.19108 (7)	0.23531 (5)	0.0841 (3)
Cl2	0.37469 (8)	0.22580 (7)	0.01857 (5)	0.0865 (3)
N1	0.7575 (2)	0.17426 (13)	0.24382 (12)	0.0457 (5)
N2	0.7540 (2)	0.11902 (14)	0.17364 (13)	0.0522 (5)
N3	0.0850 (2)	0.19699 (13)	−0.00094 (11)	0.0443 (5)
N4	0.0897 (2)	0.13575 (14)	0.06455 (12)	0.0508 (5)
O1	0.87374 (17)	0.30941 (12)	0.23266 (10)	0.0525 (5)
H1	0.9088	0.2968	0.2782	0.079*
O2	0.7846 (2)	0.19093 (13)	0.37965 (11)	0.0621 (5)
O3	−0.03948 (17)	0.32648 (13)	0.01884 (10)	0.0548 (5)
H3A	−0.0705	0.3216	−0.0289	0.082*
O4	0.04921 (19)	0.22575 (12)	−0.13467 (10)	0.0562 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0586 (18)	0.090 (2)	0.0407 (16)	0.0137 (15)	0.0055 (13)	0.0096 (14)
C2	0.0569 (16)	0.0557 (16)	0.0319 (13)	0.0083 (12)	0.0006 (11)	0.0080 (11)
C3	0.092 (2)	0.0540 (17)	0.0465 (16)	0.0113 (15)	0.0059 (15)	0.0048 (13)
C4	0.148 (4)	0.068 (2)	0.056 (2)	0.040 (2)	0.015 (2)	0.0058 (17)
C5	0.125 (4)	0.124 (4)	0.061 (2)	0.076 (3)	0.025 (2)	0.014 (2)
C6	0.072 (2)	0.133 (3)	0.064 (2)	0.037 (2)	0.0174 (17)	0.017 (2)
C7	0.0456 (14)	0.0472 (14)	0.0348 (13)	−0.0022 (10)	0.0012 (10)	0.0062 (10)
C8	0.0484 (14)	0.0532 (15)	0.0333 (13)	−0.0031 (11)	0.0005 (10)	0.0055 (11)
C9	0.0489 (15)	0.0547 (15)	0.0366 (13)	−0.0019 (11)	0.0000 (11)	0.0008 (11)
C10	0.077 (2)	0.0695 (18)	0.0415 (15)	0.0044 (15)	−0.0013 (14)	−0.0070 (13)
C11	0.0562 (16)	0.0556 (16)	0.0412 (15)	−0.0062 (12)	−0.0019 (12)	0.0097 (12)
C12	0.123 (3)	0.0602 (19)	0.0563 (18)	−0.0050 (18)	−0.0099 (19)	0.0154 (15)
C13	0.0633 (19)	0.084 (2)	0.0388 (15)	−0.0168 (15)	0.0021 (13)	−0.0014 (14)
C14	0.0620 (17)	0.0494 (15)	0.0295 (12)	−0.0092 (12)	0.0039 (11)	−0.0054 (10)
C15	0.103 (2)	0.0453 (16)	0.0503 (17)	−0.0065 (15)	0.0106 (16)	−0.0037 (13)
C16	0.161 (4)	0.057 (2)	0.067 (2)	−0.032 (2)	0.019 (2)	0.0005 (16)
C17	0.145 (4)	0.108 (3)	0.072 (2)	−0.068 (3)	0.029 (3)	0.000 (2)
C18	0.080 (2)	0.133 (3)	0.061 (2)	−0.039 (2)	0.0171 (18)	−0.007 (2)
C19	0.0475 (14)	0.0461 (13)	0.0340 (13)	0.0015 (10)	0.0010 (10)	−0.0024 (10)
C20	0.0494 (15)	0.0553 (15)	0.0323 (13)	−0.0012 (11)	0.0003 (11)	−0.0026 (11)
C21	0.0447 (14)	0.0539 (15)	0.0383 (14)	0.0022 (11)	0.0022 (11)	0.0031 (11)
C22	0.0665 (18)	0.0631 (17)	0.0398 (14)	0.0044 (14)	0.0052 (12)	0.0092 (12)
C23	0.0493 (15)	0.0513 (14)	0.0355 (13)	0.0007 (11)	0.0009 (11)	−0.0032 (11)
C24	0.109 (3)	0.0518 (17)	0.0513 (17)	0.0034 (16)	0.0051 (16)	−0.0105 (13)
Cl1	0.0578 (5)	0.1235 (8)	0.0712 (6)	−0.0265 (4)	0.0062 (4)	−0.0022 (5)
Cl2	0.0548 (5)	0.1328 (8)	0.0718 (6)	0.0203 (5)	0.0049 (4)	0.0159 (5)
N1	0.0562 (13)	0.0474 (12)	0.0329 (11)	−0.0004 (9)	−0.0002 (9)	0.0033 (9)
N2	0.0632 (14)	0.0517 (13)	0.0409 (12)	−0.0004 (10)	0.0007 (10)	−0.0042 (10)
N3	0.0593 (13)	0.0433 (11)	0.0297 (10)	−0.0032 (9)	0.0010 (9)	0.0015 (8)
N4	0.0657 (14)	0.0487 (12)	0.0375 (12)	−0.0013 (10)	0.0016 (10)	0.0055 (10)
O1	0.0500 (11)	0.0672 (12)	0.0394 (10)	−0.0108 (8)	−0.0015 (8)	0.0060 (8)
O2	0.0814 (14)	0.0671 (12)	0.0357 (10)	−0.0027 (10)	−0.0057 (9)	0.0036 (9)
O3	0.0541 (11)	0.0728 (12)	0.0372 (10)	0.0132 (9)	0.0018 (8)	−0.0012 (9)
O4	0.0762 (13)	0.0562 (11)	0.0345 (10)	−0.0032 (9)	−0.0052 (9)	0.0011 (8)

C1—C6	1.378 (4)	C13—Cl2	1.748 (3)
C1—C2	1.398 (4)	C14—C15	1.393 (4)
C1—Cl1	1.746 (3)	C14—C19	1.527 (3)
C2—C3	1.383 (4)	C15—C16	1.383 (5)
C2—C7	1.527 (3)	C15—H15	0.9300
C3—C4	1.393 (5)	C16—C17	1.357 (6)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.375 (6)	C17—C18	1.391 (6)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.369 (6)	C18—H18	0.9300
C5—H5	0.9300	C19—O3	1.399 (3)
C6—H6	0.9300	C19—N3	1.477 (3)
C7—O1	1.400 (3)	C19—C20	1.538 (3)
C7—N1	1.481 (3)	C20—C21	1.491 (3)
C7—C8	1.539 (3)	C20—H20A	0.9700
C8—C9	1.484 (4)	C20—H20B	0.9700
C8—H8A	0.9700	C21—N4	1.281 (3)
C8—H8B	0.9700	C21—C22	1.492 (3)
C9—N2	1.283 (3)	C22—H22A	0.9600
C9—C10	1.492 (3)	C22—H22B	0.9600
C10—H10A	0.9600	C22—H22C	0.9600
C10—H10B	0.9600	C23—O4	1.229 (3)
C10—H10C	0.9600	C23—N3	1.348 (3)
C11—O2	1.220 (3)	C23—C24	1.490 (4)
C11—N1	1.350 (3)	C24—H24A	0.9600
C11—C12	1.503 (4)	C24—H24B	0.9600
C12—H12A	0.9600	C24—H24C	0.9600
C12—H12B	0.9600	N1—N2	1.410 (3)
C12—H12C	0.9600	N3—N4	1.405 (3)
C13—C14	1.389 (4)	O1—H1	0.8200
C13—C18	1.391 (4)	O3—H3A	0.8200
C6—C1—C2	121.7 (3)	C15—C14—C19	119.3 (3)
C6—C1—Cl1	116.9 (3)	C16—C15—C14	121.5 (4)
C2—C1—Cl1	121.3 (2)	C16—C15—H15	119.3
C3—C2—C1	117.2 (3)	C14—C15—H15	119.3
C3—C2—C7	119.0 (2)	C17—C16—C15	120.2 (4)
C1—C2—C7	123.4 (2)	C17—C16—H16	119.9
C2—C3—C4	121.4 (3)	C15—C16—H16	119.9
C2—C3—H3	119.3	C16—C17—C18	120.7 (3)
C4—C3—H3	119.3	C16—C17—H17	119.6
C5—C4—C3	119.5 (4)	C18—C17—H17	119.6
C5—C4—H4	120.3	C13—C18—C17	118.5 (4)
C3—C4—H4	120.3	C13—C18—H18	120.8
C6—C5—C4	120.5 (3)	C17—C18—H18	120.8
C6—C5—H5	119.7	O3—C19—N3	110.10 (19)
C4—C5—H5	119.7	O3—C19—C14	112.1 (2)
C5—C6—C1	119.6 (4)	N3—C19—C14	112.44 (19)
C5—C6—H6	120.2	O3—C19—C20	106.78 (19)
C1—C6—H6	120.2	N3—C19—C20	100.30 (18)
O1—C7—N1	110.09 (19)	C14—C19—C20	114.4 (2)
O1—C7—C2	112.0 (2)	C21—C20—C19	103.33 (19)
N1—C7—C2	113.86 (19)	C21—C20—H20A	111.1
O1—C7—C8	106.87 (19)	C19—C20—H20A	111.1
N1—C7—C8	100.51 (18)	C21—C20—H20B	111.1
C2—C7—C8	112.74 (19)	C19—C20—H20B	111.1
C9—C8—C7	103.38 (19)	H20A—C20—H20B	109.1
C9—C8—H8A	111.1	N4—C21—C20	114.1 (2)
C7—C8—H8A	111.1	N4—C21—C22	121.4 (2)
C9—C8—H8B	111.1	C20—C21—C22	124.5 (2)
C7—C8—H8B	111.1	C21—C22—H22A	109.5
H8A—C8—H8B	109.1	C21—C22—H22B	109.5
N2—C9—C8	114.6 (2)	H22A—C22—H22B	109.5
N2—C9—C10	122.3 (2)	C21—C22—H22C	109.5
C8—C9—C10	123.2 (2)	H22A—C22—H22C	109.5
C9—C10—H10A	109.5	H22B—C22—H22C	109.5
C9—C10—H10B	109.5	O4—C23—N3	119.4 (2)
H10A—C10—H10B	109.5	O4—C23—C24	122.5 (2)
C9—C10—H10C	109.5	N3—C23—C24	118.2 (2)
H10A—C10—H10C	109.5	C23—C24—H24A	109.5
H10B—C10—H10C	109.5	C23—C24—H24B	109.5
O2—C11—N1	120.0 (2)	H24A—C24—H24B	109.5
O2—C11—C12	123.1 (2)	C23—C24—H24C	109.5
N1—C11—C12	116.9 (2)	H24A—C24—H24C	109.5
C11—C12—H12A	109.5	H24B—C24—H24C	109.5
C11—C12—H12B	109.5	C11—N1—N2	122.0 (2)
H12A—C12—H12B	109.5	C11—N1—C7	125.3 (2)
C11—C12—H12C	109.5	N2—N1—C7	112.58 (18)
H12A—C12—H12C	109.5	C9—N2—N1	107.4 (2)
H12B—C12—H12C	109.5	C23—N3—N4	121.4 (2)
C14—C13—C18	122.1 (3)	C23—N3—C19	125.1 (2)
C14—C13—Cl2	121.0 (2)	N4—N3—C19	112.90 (18)
C18—C13—Cl2	116.9 (3)	C21—N4—N3	107.6 (2)
C13—C14—C15	117.1 (3)	C7—O1—H1	109.5
C13—C14—C19	123.6 (2)	C19—O3—H3A	109.5
C6—C1—C2—C3	−0.8 (4)	C15—C14—C19—N3	130.6 (2)
Cl1—C1—C2—C3	179.10 (19)	C13—C14—C19—C20	61.5 (3)
C6—C1—C2—C7	−174.6 (2)	C15—C14—C19—C20	−115.9 (3)
Cl1—C1—C2—C7	5.4 (3)	O3—C19—C20—C21	102.6 (2)
C1—C2—C3—C4	0.6 (4)	N3—C19—C20—C21	−12.3 (2)
C7—C2—C3—C4	174.6 (2)	C14—C19—C20—C21	−132.8 (2)
C2—C3—C4—C5	−0.7 (5)	C19—C20—C21—N4	9.7 (3)
C3—C4—C5—C6	1.1 (5)	C19—C20—C21—C22	−170.9 (2)
C4—C5—C6—C1	−1.4 (5)	O2—C11—N1—N2	176.0 (2)
C2—C1—C6—C5	1.2 (5)	C12—C11—N1—N2	−4.6 (4)
Cl1—C1—C6—C5	−178.7 (3)	O2—C11—N1—C7	0.7 (4)
C3—C2—C7—O1	11.4 (3)	C12—C11—N1—C7	−179.8 (3)
C1—C2—C7—O1	−175.0 (2)	O1—C7—N1—C11	75.2 (3)
C3—C2—C7—N1	137.2 (2)	C2—C7—N1—C11	−51.5 (3)
C1—C2—C7—N1	−49.2 (3)	C8—C7—N1—C11	−172.3 (2)
C3—C2—C7—C8	−109.1 (2)	O1—C7—N1—N2	−100.4 (2)
C1—C2—C7—C8	64.5 (3)	C2—C7—N1—N2	132.8 (2)
O1—C7—C8—C9	103.5 (2)	C8—C7—N1—N2	12.0 (2)
N1—C7—C8—C9	−11.4 (2)	C8—C9—N2—N1	−1.1 (3)
C2—C7—C8—C9	−133.0 (2)	C10—C9—N2—N1	179.5 (2)
C7—C8—C9—N2	8.5 (3)	C11—N1—N2—C9	176.7 (2)
C7—C8—C9—C10	−172.0 (2)	C7—N1—N2—C9	−7.5 (3)
C18—C13—C14—C15	0.0 (4)	O4—C23—N3—N4	173.4 (2)
Cl2—C13—C14—C15	−179.9 (2)	C24—C23—N3—N4	−7.5 (4)
C18—C13—C14—C19	−177.4 (3)	O4—C23—N3—C19	2.1 (4)
Cl2—C13—C14—C19	2.7 (3)	C24—C23—N3—C19	−178.8 (2)
C13—C14—C15—C16	1.0 (4)	O3—C19—N3—C23	72.1 (3)
C19—C14—C15—C16	178.6 (3)	C14—C19—N3—C23	−53.7 (3)
C14—C15—C16—C17	−1.4 (5)	C20—C19—N3—C23	−175.6 (2)
C15—C16—C17—C18	0.8 (6)	O3—C19—N3—N4	−99.7 (2)
C14—C13—C18—C17	−0.7 (5)	C14—C19—N3—N4	134.4 (2)
Cl2—C13—C18—C17	179.2 (3)	C20—C19—N3—N4	12.5 (3)
C16—C17—C18—C13	0.3 (6)	C20—C21—N4—N3	−1.9 (3)
C13—C14—C19—O3	−176.7 (2)	C22—C21—N4—N3	178.6 (2)
C15—C14—C19—O3	5.9 (3)	C23—N3—N4—C21	−179.6 (2)
C13—C14—C19—N3	−52.0 (3)	C19—N3—N4—C21	−7.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—–H1···..O4i	0.82	1.97	2.748 (3)	159
O3—–H3A···..O2ii	0.82	2.03	2.792 (3)	155
C8—–H8B···..O3iii	0.97	2.53	3.410 (3)	151
C20—–H20B···..O1iv	0.97	2.50	3.354 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—–H1⋯..O4i	0.82	1.97	2.748 (3)	159
O3—–H3A⋯..O2ii	0.82	2.03	2.792 (3)	155
C8—–H8B⋯..O3iii	0.97	2.53	3.410 (3)	151
C20—–H20B⋯..O1iv	0.97	2.50	3.354 (3)	147

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