1,5-Dimethyl-2-phenyl-4-{[(E)-3,4,5-trimethoxybenzylidene]amino}-1H-pyrazol-3(2H)-one

Liu, S.-B.; Bi, C.-F.; Fan, Y.-H.; Zhang, X.; Zhang, D.-M.

doi:10.1107/S160053681002934X

1,5-Dimethyl-2-phenyl-4-{[(E)-3,4,5-trimethoxybenzylidene]amino}-1H-pyrazol-3(2H)-one

S.-B. Liu, C.-F. Bi, Y.-H. Fan, X. Zhang and D.-M. Zhang

In the title compound, C₂₁H₂₃N₃O₄, the pyrazole ring forms dihedral angles of 21.58 (8) and 66.64 (7)° with the benzene and phenyl rings, respectively. The crystal structure is stabilized by weak intermolecular C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053681002934X/lh5091sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053681002934X/lh5091Isup2.hkl Contains datablock I

CCDC reference: 779969

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.042
wR factor = 0.098
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          5
PLAT145_ALERT_4_C su on beta     Small or Missing  (x 10000) .....          1 Deg.

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

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

Comment top

Schiff bases are among the most fundamental chelating systems in coordination chemistry (Atwood et al., 2001; Che et al., 2003). The metal complexes based on this type ligands have expanded enormously areas of catalytic activities (Drozdzak et al., 2005), molecular magnetism (Yuan et al., 2007) and biological activities, such as antitumor activities (Adsule et al., 2006). The examples given above clearly demonstrate that Schiff base ligands are of special interest in the field of chemistry. Herein, we present the synthesis and crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The bond lengths and angles can be compared to those in a related structure (Sun et al., 2007). The dihedral angles between the pyrazole ring and the benzene and phenyl rings are 21.58 (8)° and 66.64 (7)°, respectively. The crystal structure is stabilized by by weak intermolecular C—H···O hydrogen bonds.

Related literature top

For general background to Schiff base compounds, see: Atwood et al. (2001); Che et al. (2003). For the applications of metal–Schiff base complexes, see: Drozdzak et al. (2005); Adsule et al. (2006); Yuan et al. (2007). For a related structure, see: Sun et al. (2007).

Experimental top

4-aminoantpyrine (10 mmol, 2.032 g) was added with stirring to anhydrous ethanol (30 ml) and an anhydrous ethanol solution (10 ml) of 3,4,5-trimethoxybenzaldehyde (10 mmol, 1.962 g) was slowly added. The reaction mixture was stirred at 353 K for 5 h, whereupon a yellow solid separated out. The precipitate formed was filtered off, washed several times with anhydrous ethanol and dried under vacuum. Yellow block-shaped crystals were obtained from an anhydrous ethanol solution of the title compound after 2 days by slow evaporation at room temperature.

Structure description top

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Part of the crystal structure showing weak C—H···O hydrogen bonds as dashed lines. Only H atoms involved in hydrogen bonds are shown.

1,5-Dimethyl-2-phenyl-4-{[(E)-3,4,5-trimethoxybenzylidene]amino}- 1H-pyrazol-3(2H)-one top

Crystal data top

C₂₁H₂₃N₃O₄	F(000) = 808
M_r = 381.42	D_x = 1.306 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2128 reflections
a = 12.3644 (12) Å	θ = 2.2–25.3°
b = 14.0075 (16) Å	µ = 0.09 mm⁻¹
c = 11.2682 (11) Å	T = 298 K
β = 96.4680 (1)°	Block, yellow
V = 1939.2 (3) Å³	0.40 × 0.17 × 0.13 mm
Z = 4

Data collection top

Siemens SMART CCD diffractometer	3422 independent reflections
Radiation source: fine-focus sealed tube	2084 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
φ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.964, T_max = 0.988	k = −16→12
10089 measured reflections	l = −13→13

Refinement top

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: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.039P)²] where P = (F_o² + 2F_c²)/3
3422 reflections	(Δ/σ)_max < 0.001
258 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₁H₂₃N₃O₄	V = 1939.2 (3) Å³
M_r = 381.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3644 (12) Å	µ = 0.09 mm⁻¹
b = 14.0075 (16) Å	T = 298 K
c = 11.2682 (11) Å	0.40 × 0.17 × 0.13 mm
β = 96.4680 (1)°

Data collection top

Siemens SMART CCD diffractometer	3422 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2084 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.988	R_int = 0.038
10089 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 0.99	Δρ_max = 0.15 e Å⁻³
3422 reflections	Δρ_min = −0.18 e Å⁻³
258 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.58862 (12)	0.17160 (11)	0.75617 (14)	0.0483 (4)
N2	0.55362 (12)	0.07674 (11)	0.73659 (14)	0.0488 (4)
N3	0.38480 (12)	0.18932 (11)	0.49987 (13)	0.0456 (4)
O1	0.56035 (11)	0.31372 (9)	0.65254 (13)	0.0616 (4)
O2	0.14379 (11)	0.51801 (9)	0.24428 (12)	0.0597 (4)
O3	0.06093 (10)	0.38623 (9)	0.08868 (12)	0.0555 (4)
O4	0.12137 (12)	0.20441 (10)	0.10776 (12)	0.0641 (4)
C1	0.53561 (15)	0.22988 (14)	0.66664 (17)	0.0451 (5)
C2	0.45678 (14)	0.16819 (13)	0.60050 (16)	0.0415 (5)
C3	0.46934 (14)	0.07841 (13)	0.64717 (17)	0.0425 (5)
C4	0.40708 (16)	−0.00978 (13)	0.61267 (19)	0.0568 (6)
H4A	0.4568	−0.0613	0.6042	0.085*
H4B	0.3628	0.0004	0.5382	0.085*
H4C	0.3614	−0.0255	0.6733	0.085*
C5	0.55506 (17)	0.01888 (15)	0.8440 (2)	0.0682 (7)
H5A	0.5077	0.0468	0.8963	0.102*
H5B	0.6278	0.0162	0.8838	0.102*
H5C	0.5306	−0.0445	0.8227	0.102*
C6	0.70012 (16)	0.18510 (13)	0.80311 (17)	0.0460 (5)
C7	0.72641 (19)	0.24765 (15)	0.89492 (19)	0.0645 (6)
H7	0.6722	0.2807	0.9286	0.077*
C8	0.8353 (2)	0.26125 (18)	0.9374 (2)	0.0788 (8)
H8	0.8544	0.3047	0.9985	0.095*
C9	0.9143 (2)	0.2109 (2)	0.8894 (3)	0.0798 (8)
H9	0.9871	0.2200	0.9182	0.096*
C10	0.88698 (18)	0.14758 (18)	0.7999 (2)	0.0765 (7)
H10	0.9411	0.1129	0.7683	0.092*
C11	0.78040 (17)	0.13441 (15)	0.7557 (2)	0.0613 (6)
H11	0.7622	0.0913	0.6939	0.074*
C12	0.36413 (15)	0.27582 (14)	0.47241 (17)	0.0478 (5)
H12	0.3986	0.3235	0.5201	0.057*
C13	0.28837 (15)	0.30404 (13)	0.36894 (16)	0.0429 (5)
C14	0.25703 (15)	0.39875 (13)	0.35636 (17)	0.0463 (5)
H14	0.2868	0.4437	0.4114	0.056*
C15	0.18193 (15)	0.42704 (13)	0.26269 (17)	0.0439 (5)
C16	0.13902 (15)	0.36017 (14)	0.17957 (17)	0.0446 (5)
C17	0.17022 (15)	0.26509 (14)	0.19268 (16)	0.0460 (5)
C18	0.24460 (15)	0.23685 (14)	0.28662 (16)	0.0461 (5)
H18	0.2653	0.1731	0.2947	0.055*
C19	0.17650 (18)	0.58758 (14)	0.33332 (19)	0.0658 (6)
H19A	0.1578	0.5659	0.4092	0.099*
H19B	0.1400	0.6468	0.3129	0.099*
H19C	0.2538	0.5970	0.3379	0.099*
C20	0.10337 (18)	0.41981 (17)	−0.01563 (19)	0.0735 (7)
H20A	0.1388	0.4801	0.0009	0.110*
H20B	0.0450	0.4275	−0.0787	0.110*
H20C	0.1549	0.3745	−0.0396	0.110*
C21	0.12836 (19)	0.10573 (14)	0.1296 (2)	0.0703 (7)
H21A	0.2030	0.0859	0.1341	0.105*
H21B	0.0864	0.0722	0.0660	0.105*
H21C	0.1005	0.0917	0.2038	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0450 (10)	0.0437 (10)	0.0528 (11)	−0.0016 (8)	−0.0099 (8)	0.0052 (8)
N2	0.0480 (10)	0.0402 (10)	0.0556 (11)	−0.0017 (8)	−0.0053 (8)	0.0121 (9)
N3	0.0477 (10)	0.0446 (10)	0.0427 (10)	0.0030 (7)	−0.0027 (8)	0.0051 (8)
O1	0.0657 (10)	0.0377 (9)	0.0756 (11)	−0.0008 (7)	−0.0176 (8)	0.0059 (7)
O2	0.0717 (10)	0.0454 (9)	0.0582 (9)	0.0105 (7)	−0.0101 (8)	0.0030 (7)
O3	0.0515 (9)	0.0663 (10)	0.0453 (9)	0.0047 (7)	−0.0093 (7)	0.0096 (7)
O4	0.0802 (11)	0.0523 (10)	0.0538 (9)	−0.0018 (7)	−0.0188 (8)	−0.0043 (8)
C1	0.0445 (12)	0.0400 (12)	0.0493 (13)	0.0061 (9)	−0.0022 (9)	0.0020 (10)
C2	0.0419 (11)	0.0415 (12)	0.0397 (12)	0.0043 (9)	−0.0018 (9)	0.0029 (9)
C3	0.0392 (11)	0.0427 (12)	0.0450 (12)	0.0038 (9)	0.0019 (9)	0.0027 (10)
C4	0.0553 (13)	0.0479 (13)	0.0663 (15)	−0.0039 (10)	0.0024 (11)	0.0001 (11)
C5	0.0662 (15)	0.0656 (15)	0.0695 (16)	−0.0030 (12)	−0.0064 (12)	0.0279 (13)
C6	0.0470 (12)	0.0438 (12)	0.0441 (12)	−0.0020 (10)	−0.0088 (10)	0.0079 (10)
C7	0.0706 (16)	0.0645 (15)	0.0557 (14)	0.0010 (12)	−0.0050 (12)	−0.0033 (12)
C8	0.089 (2)	0.0772 (18)	0.0617 (16)	−0.0245 (16)	−0.0266 (15)	−0.0002 (14)
C9	0.0563 (16)	0.085 (2)	0.091 (2)	−0.0145 (14)	−0.0253 (15)	0.0310 (17)
C10	0.0463 (15)	0.0813 (18)	0.101 (2)	0.0010 (12)	0.0043 (14)	0.0130 (16)
C11	0.0518 (14)	0.0638 (15)	0.0668 (16)	0.0008 (11)	−0.0005 (12)	−0.0037 (12)
C12	0.0491 (12)	0.0481 (13)	0.0437 (12)	0.0007 (10)	−0.0051 (9)	0.0011 (10)
C13	0.0425 (11)	0.0478 (12)	0.0367 (11)	0.0008 (9)	−0.0027 (9)	0.0051 (10)
C14	0.0513 (12)	0.0453 (12)	0.0403 (12)	−0.0034 (9)	−0.0038 (9)	0.0006 (9)
C15	0.0455 (12)	0.0415 (11)	0.0437 (12)	0.0031 (9)	0.0001 (9)	0.0061 (10)
C16	0.0407 (11)	0.0524 (13)	0.0387 (12)	0.0022 (9)	−0.0039 (9)	0.0072 (10)
C17	0.0500 (12)	0.0494 (13)	0.0372 (12)	−0.0040 (10)	−0.0012 (10)	−0.0016 (10)
C18	0.0515 (12)	0.0425 (12)	0.0429 (12)	0.0027 (9)	−0.0010 (10)	0.0035 (10)
C19	0.0833 (17)	0.0464 (13)	0.0663 (15)	0.0053 (12)	0.0020 (13)	−0.0007 (12)
C20	0.0790 (17)	0.0973 (19)	0.0432 (14)	0.0217 (14)	0.0019 (12)	0.0140 (13)
C21	0.0875 (18)	0.0523 (15)	0.0675 (16)	−0.0072 (12)	−0.0063 (13)	−0.0076 (12)

Geometric parameters (Å, º) top

N1—C1	1.402 (2)	C8—C9	1.364 (3)
N1—N2	1.407 (2)	C8—H8	0.9300
N1—C6	1.432 (2)	C9—C10	1.357 (3)
N2—C3	1.366 (2)	C9—H9	0.9300
N2—C5	1.455 (2)	C10—C11	1.368 (3)
N3—C12	1.269 (2)	C10—H10	0.9300
N3—C2	1.392 (2)	C11—H11	0.9300
O1—C1	1.228 (2)	C12—C13	1.465 (3)
O2—C15	1.367 (2)	C12—H12	0.9300
O2—C19	1.424 (2)	C13—C14	1.385 (2)
O3—C16	1.375 (2)	C13—C18	1.388 (2)
O3—C20	1.420 (2)	C14—C15	1.383 (3)
O4—C17	1.368 (2)	C14—H14	0.9300
O4—C21	1.405 (2)	C15—C16	1.387 (3)
C1—C2	1.445 (3)	C16—C17	1.390 (3)
C2—C3	1.365 (2)	C17—C18	1.380 (2)
C3—C4	1.484 (2)	C18—H18	0.9300
C4—H4A	0.9600	C19—H19A	0.9600
C4—H4B	0.9600	C19—H19B	0.9600
C4—H4C	0.9600	C19—H19C	0.9600
C5—H5A	0.9600	C20—H20A	0.9600
C5—H5B	0.9600	C20—H20B	0.9600
C5—H5C	0.9600	C20—H20C	0.9600
C6—C7	1.367 (3)	C21—H21A	0.9600
C6—C11	1.376 (3)	C21—H21B	0.9600
C7—C8	1.391 (3)	C21—H21C	0.9600
C7—H7	0.9300

C1—N1—N2	109.06 (15)	C9—C10—H10	119.7
C1—N1—C6	122.78 (15)	C11—C10—H10	119.7
N2—N1—C6	116.67 (14)	C10—C11—C6	119.8 (2)
C3—N2—N1	107.16 (14)	C10—C11—H11	120.1
C3—N2—C5	124.06 (15)	C6—C11—H11	120.1
N1—N2—C5	114.90 (16)	N3—C12—C13	122.99 (18)
C12—N3—C2	119.61 (16)	N3—C12—H12	118.5
C15—O2—C19	117.73 (15)	C13—C12—H12	118.5
C16—O3—C20	114.23 (15)	C14—C13—C18	119.85 (18)
C17—O4—C21	118.35 (16)	C14—C13—C12	119.09 (18)
O1—C1—N1	123.15 (18)	C18—C13—C12	121.01 (17)
O1—C1—C2	131.93 (18)	C15—C14—C13	120.58 (18)
N1—C1—C2	104.86 (16)	C15—C14—H14	119.7
C3—C2—N3	122.96 (17)	C13—C14—H14	119.7
C3—C2—C1	108.14 (16)	O2—C15—C14	125.01 (18)
N3—C2—C1	128.69 (17)	O2—C15—C16	115.34 (17)
C2—C3—N2	110.13 (16)	C14—C15—C16	119.65 (17)
C2—C3—C4	129.25 (18)	O3—C16—C15	120.43 (17)
N2—C3—C4	120.61 (17)	O3—C16—C17	119.79 (18)
C3—C4—H4A	109.5	C15—C16—C17	119.65 (18)
C3—C4—H4B	109.5	O4—C17—C18	124.20 (18)
H4A—C4—H4B	109.5	O4—C17—C16	115.18 (17)
C3—C4—H4C	109.5	C18—C17—C16	120.62 (18)
H4A—C4—H4C	109.5	C17—C18—C13	119.64 (18)
H4B—C4—H4C	109.5	C17—C18—H18	120.2
N2—C5—H5A	109.5	C13—C18—H18	120.2
N2—C5—H5B	109.5	O2—C19—H19A	109.5
H5A—C5—H5B	109.5	O2—C19—H19B	109.5
N2—C5—H5C	109.5	H19A—C19—H19B	109.5
H5A—C5—H5C	109.5	O2—C19—H19C	109.5
H5B—C5—H5C	109.5	H19A—C19—H19C	109.5
C7—C6—C11	120.3 (2)	H19B—C19—H19C	109.5
C7—C6—N1	120.07 (19)	O3—C20—H20A	109.5
C11—C6—N1	119.66 (18)	O3—C20—H20B	109.5
C6—C7—C8	119.1 (2)	H20A—C20—H20B	109.5
C6—C7—H7	120.4	O3—C20—H20C	109.5
C8—C7—H7	120.4	H20A—C20—H20C	109.5
C9—C8—C7	120.1 (2)	H20B—C20—H20C	109.5
C9—C8—H8	120.0	O4—C21—H21A	109.5
C7—C8—H8	120.0	O4—C21—H21B	109.5
C10—C9—C8	120.2 (2)	H21A—C21—H21B	109.5
C10—C9—H9	119.9	O4—C21—H21C	109.5
C8—C9—H9	119.9	H21A—C21—H21C	109.5
C9—C10—C11	120.5 (2)	H21B—C21—H21C	109.5

C1—N1—N2—C3	−8.40 (19)	C8—C9—C10—C11	0.9 (4)
C6—N1—N2—C3	−152.94 (16)	C9—C10—C11—C6	−0.6 (4)
C1—N1—N2—C5	−150.54 (16)	C7—C6—C11—C10	−0.8 (3)
C6—N1—N2—C5	64.9 (2)	N1—C6—C11—C10	179.61 (18)
N2—N1—C1—O1	−170.55 (17)	C2—N3—C12—C13	−179.20 (16)
C6—N1—C1—O1	−28.6 (3)	N3—C12—C13—C14	169.61 (17)
N2—N1—C1—C2	6.95 (19)	N3—C12—C13—C18	−7.8 (3)
C6—N1—C1—C2	148.88 (17)	C18—C13—C14—C15	0.3 (3)
C12—N3—C2—C3	168.73 (17)	C12—C13—C14—C15	−177.09 (17)
C12—N3—C2—C1	−17.2 (3)	C19—O2—C15—C14	−5.6 (3)
O1—C1—C2—C3	174.1 (2)	C19—O2—C15—C16	173.74 (17)
N1—C1—C2—C3	−3.0 (2)	C13—C14—C15—O2	178.25 (17)
O1—C1—C2—N3	−0.6 (3)	C13—C14—C15—C16	−1.1 (3)
N1—C1—C2—N3	−177.84 (17)	C20—O3—C16—C15	88.4 (2)
N3—C2—C3—N2	173.05 (16)	C20—O3—C16—C17	−95.6 (2)
C1—C2—C3—N2	−2.1 (2)	O2—C15—C16—O3	−2.1 (3)
N3—C2—C3—C4	−6.2 (3)	C14—C15—C16—O3	177.30 (16)
C1—C2—C3—C4	178.61 (18)	O2—C15—C16—C17	−178.04 (16)
N1—N2—C3—C2	6.4 (2)	C14—C15—C16—C17	1.3 (3)
C5—N2—C3—C2	144.21 (18)	C21—O4—C17—C18	14.1 (3)
N1—N2—C3—C4	−174.22 (15)	C21—O4—C17—C16	−165.26 (17)
C5—N2—C3—C4	−36.4 (3)	O3—C16—C17—O4	2.5 (3)
C1—N1—C6—C7	86.2 (2)	C15—C16—C17—O4	178.47 (17)
N2—N1—C6—C7	−134.48 (18)	O3—C16—C17—C18	−176.90 (16)
C1—N1—C6—C11	−94.1 (2)	C15—C16—C17—C18	−0.9 (3)
N2—N1—C6—C11	45.2 (2)	O4—C17—C18—C13	−179.14 (17)
C11—C6—C7—C8	1.8 (3)	C16—C17—C18—C13	0.2 (3)
N1—C6—C7—C8	−178.59 (18)	C14—C13—C18—C17	0.1 (3)
C6—C7—C8—C9	−1.5 (3)	C12—C13—C18—C17	177.48 (17)
C7—C8—C9—C10	0.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5C···O1ⁱ	0.96	2.31	3.211 (2)	155
C9—H9···O4ⁱⁱ	0.93	2.56	3.346 (3)	142

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₃N₃O₄
M_r	381.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.3644 (12), 14.0075 (16), 11.2682 (11)
β (°)	96.4680 (1)
V (Å³)	1939.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.17 × 0.13

Data collection
Diffractometer	Siemens SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.964, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	10089, 3422, 2084
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.098, 0.99
No. of reflections	3422
No. of parameters	258
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.18

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5C···O1ⁱ	0.96	2.31	3.211 (2)	155
C9—H9···O4ⁱⁱ	0.93	2.56	3.346 (3)	142

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x+1, y, z+1.

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