2-[(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methyl­idene]indan-1,3-dione

Asiri, A.M.; Al-Youbi, A.O.; Khan, S.A.; Tahir, M.N.

doi:10.1107/S1600536811049488

2-[(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methylidene]indan-1,3-dione

A. M. Asiri, A. O. Al-Youbi, S. A. Khan and M. N. Tahir

In the title compound, C₂₁H₁₆N₂O₂, the five-membered heterocyclic ring makes a dihedral angle of 47.06 (6)° with the attached benzene ring, whereas the indan-1,3-dione ring system and the benzene ring are oriented at a dihedral angle of 21.92 (7)°. In the crystal, inversion dimers linked by pairs of C—H

O hydrogen bonds generate R₂²(22) loops. Aromatic π–π stacking interactions [centroid–centroid distances = 3.8325 (12)–3.8600 (12) Å] also occur.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811049488/hb6509sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811049488/hb6509Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536811049488/hb6509Isup3.cml Supplementary material

CCDC reference: 858487

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.042
wR factor = 0.112
Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          44 Perc.

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Formation of the donor acceptor chromophores by the nucleophilic addition of an active hydrogen compound to a carbonyl group followed by a dehydration reaction is known as knoevenagel condensation (Asiri & Khan, 2009). Donor acceptor chromophores are applicable in the field of materials science such as third order non-linear optical (NLO) (Asiri et al. 2006), photonic materials and devices, optical limiting (Kulhanek et al. 2011), electrochemical sensing (Koyuncu et al. 2010) and langmuir film (Wang et al. 2011). Due to wide application of donor acceptor chromophores, we are reporting here the synthesiz and crystal structure of the title compound (I), (Fig. 1).

The crystal structures of (II) i.e., 2-(4,5,6,7,8,9-hexahydro-6a-azaphenylen-2-ylmethylene)indan-1,3-dione (Belyakov et al., 2008) and (III) i.e., 4-((E)((3,5-dimethyl- 1-phenyl-1H-pyrazol-4-yl)methylene)amino)-1,5-dimethyl-2-phenyl -1,2-dihydro-3H-pyrazol-3-one have been published which contain the moities present in (I).

In (I), the group A (C1—C9/O1/O2) of indan-1, 3-dione, the heterocyclic five membered ring B (C11/C12/C14/N1/N2) and the benzene ring C (C16—C21) of the aldehyde moiety are planar with r. m. s. deviation of 0.0345, 0.0099 and 0.0035 Å, respectively. The dihedral angle between A/B, A/C and B/C is 39.77 (4), 21.92 (7) and 47.06 (6)°, respectively. The title compound consists of dimers due to intermolecular H-bonds of C—H···O type, where O-atom is of carbonyl and H-atom is of benzene ring. This H-bondings form a R₂²(22) (Fig. 2) ring motif (Bernstein et al., 1995). There exists π–π interactions between the centroids of the rings of indan-1, 3-dione moieties at the separation of 3.8325 (12)–3.8600 (12) A°.

Related literature top

For background to donor–acceptor chromophores, see: Asiri et al. (2006); Asiri & Khan (2009); Koyuncu et al. (2010); Kulhanek et al. (2011); Wang et al. (2011). For related structures, see: Belyakov et al. (2008); Fun et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

A mixture of 3,5-dimethyl-1-phenylpyrazole-4-carbaldehyde (1.0 g, 5.0 mmol), indan-1, 3-dione (0.73 g, 5.0 mmol) and a few drops of pyridine in ethanol (15 ml) was heated for 3 h. The progress of the reaction was monitored by TLC. The solid that separated from the cooled mixture was collected and recrystallized from a methanol-chloroform mixture to give the yellow prisms of (I).

Yellow: 85%, m.p. 469–470 K.

IR (KBr) ν_max cm^-1: 3035 (Ar—H), 2859 (C—H), 1663 (C═O), 1578 (C═C).

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form dimers with R₂²(22) ring motif.

2-[(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methylidene]indan-1,3-dione top

Crystal data top

C₂₁H₁₆N₂O₂	F(000) = 1376
M_r = 328.36	D_x = 1.329 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2106 reflections
a = 14.6655 (3) Å	θ = 1.4–25.3°
b = 7.8902 (2) Å	µ = 0.09 mm⁻¹
c = 28.6651 (7) Å	T = 296 K
β = 98.251 (1)°	Prism, yellow
V = 3282.61 (13) Å³	0.26 × 0.23 × 0.21 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	2970 independent reflections
Radiation source: fine-focus sealed tube	2106 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 8.00 pixels mm^-1	θ_max = 25.3°, θ_min = 1.4°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→9
T_min = 0.975, T_max = 0.985	l = −34→34
12302 measured reflections

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) = 0.112	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0522P)² + 0.9126P] where P = (F_o² + 2F_c²)/3
2970 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₁H₁₆N₂O₂	V = 3282.61 (13) Å³
M_r = 328.36	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 14.6655 (3) Å	µ = 0.09 mm⁻¹
b = 7.8902 (2) Å	T = 296 K
c = 28.6651 (7) Å	0.26 × 0.23 × 0.21 mm
β = 98.251 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2970 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2106 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.985	R_int = 0.034
12302 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.01	Δρ_max = 0.12 e Å⁻³
2970 reflections	Δρ_min = −0.23 e Å⁻³
228 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.07106 (8)	0.30881 (19)	0.11877 (4)	0.0564 (5)
O2	0.23637 (9)	0.04176 (19)	0.00898 (4)	0.0608 (5)
N1	0.34865 (9)	0.1867 (2)	0.23313 (5)	0.0473 (5)
N2	0.25797 (9)	0.1475 (2)	0.23590 (5)	0.0439 (5)
C1	0.17883 (11)	0.1490 (2)	0.07845 (6)	0.0419 (6)
C2	0.09301 (11)	0.2414 (3)	0.08361 (6)	0.0423 (6)
C3	0.03786 (11)	0.2486 (2)	0.03591 (6)	0.0403 (6)
C4	−0.04905 (12)	0.3164 (3)	0.02282 (6)	0.0475 (6)
C5	−0.08681 (13)	0.3072 (3)	−0.02408 (7)	0.0537 (7)
C6	−0.03758 (14)	0.2345 (3)	−0.05695 (7)	0.0557 (7)
C7	0.04935 (13)	0.1681 (3)	−0.04398 (6)	0.0519 (7)
C8	0.08677 (11)	0.1748 (2)	0.00319 (6)	0.0414 (6)
C9	0.17632 (12)	0.1113 (3)	0.02737 (6)	0.0450 (6)
C10	0.25407 (11)	0.1176 (2)	0.11037 (6)	0.0441 (6)
C11	0.26939 (11)	0.1368 (2)	0.16062 (6)	0.0418 (6)
C12	0.35529 (11)	0.1768 (2)	0.18786 (6)	0.0441 (6)
C13	0.44513 (12)	0.2131 (3)	0.17115 (7)	0.0616 (8)
C14	0.20881 (11)	0.1150 (2)	0.19334 (6)	0.0418 (6)
C15	0.11558 (11)	0.0380 (3)	0.18802 (6)	0.0559 (7)
C16	0.22738 (12)	0.1517 (2)	0.28101 (6)	0.0440 (6)
C17	0.14828 (13)	0.2378 (3)	0.28667 (7)	0.0577 (8)
C18	0.12018 (16)	0.2438 (3)	0.33060 (9)	0.0709 (9)
C19	0.17138 (19)	0.1645 (3)	0.36842 (8)	0.0743 (10)
C20	0.25092 (17)	0.0804 (3)	0.36263 (7)	0.0682 (9)
C21	0.27950 (13)	0.0733 (3)	0.31885 (6)	0.0536 (7)
H4	−0.08104	0.36672	0.04493	0.0570*
H5	−0.14557	0.34996	−0.03377	0.0644*
H6	−0.06392	0.23049	−0.08844	0.0668*
H7	0.08189	0.12017	−0.06624	0.0623*
H10	0.30449	0.07647	0.09756	0.0529*
H13A	0.49379	0.20906	0.19738	0.0924*
H13B	0.44309	0.32379	0.15712	0.0924*
H13C	0.45628	0.12989	0.14820	0.0924*
H15A	0.07018	0.12581	0.18772	0.0838*
H15B	0.11146	−0.03737	0.21392	0.0838*
H15C	0.10477	−0.02420	0.15897	0.0838*
H17	0.11393	0.29166	0.26111	0.0693*
H18	0.06657	0.30145	0.33466	0.0850*
H19	0.15205	0.16794	0.39792	0.0891*
H20	0.28568	0.02796	0.38831	0.0818*
H21	0.33335	0.01622	0.31488	0.0643*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0561 (8)	0.0723 (10)	0.0421 (7)	0.0083 (7)	0.0117 (6)	−0.0049 (7)
O2	0.0533 (8)	0.0730 (11)	0.0585 (8)	0.0118 (7)	0.0158 (6)	−0.0066 (7)
N1	0.0349 (8)	0.0581 (11)	0.0483 (9)	−0.0067 (7)	0.0035 (6)	−0.0007 (8)
N2	0.0348 (8)	0.0530 (10)	0.0433 (8)	−0.0046 (7)	0.0032 (6)	0.0014 (7)
C1	0.0384 (9)	0.0464 (11)	0.0407 (9)	−0.0030 (8)	0.0053 (7)	0.0007 (9)
C2	0.0416 (10)	0.0472 (12)	0.0390 (10)	−0.0033 (8)	0.0087 (8)	0.0025 (9)
C3	0.0412 (10)	0.0400 (11)	0.0402 (10)	−0.0041 (8)	0.0076 (7)	0.0044 (8)
C4	0.0455 (10)	0.0516 (13)	0.0465 (10)	0.0007 (9)	0.0106 (8)	0.0068 (9)
C5	0.0453 (11)	0.0605 (14)	0.0532 (12)	0.0008 (10)	−0.0001 (9)	0.0100 (10)
C6	0.0595 (12)	0.0637 (15)	0.0407 (10)	−0.0042 (11)	−0.0038 (9)	0.0023 (10)
C7	0.0575 (12)	0.0560 (14)	0.0424 (10)	−0.0013 (10)	0.0076 (9)	−0.0030 (9)
C8	0.0417 (10)	0.0424 (12)	0.0402 (10)	−0.0053 (8)	0.0062 (7)	0.0013 (8)
C9	0.0428 (10)	0.0458 (12)	0.0476 (10)	−0.0032 (9)	0.0103 (8)	−0.0001 (9)
C10	0.0392 (10)	0.0460 (12)	0.0474 (10)	−0.0028 (8)	0.0073 (8)	−0.0007 (9)
C11	0.0359 (9)	0.0448 (12)	0.0436 (10)	−0.0005 (8)	0.0020 (7)	0.0018 (8)
C12	0.0369 (9)	0.0488 (12)	0.0463 (10)	−0.0027 (8)	0.0045 (7)	0.0022 (9)
C13	0.0403 (10)	0.0857 (17)	0.0585 (12)	−0.0126 (11)	0.0060 (9)	0.0028 (11)
C14	0.0341 (9)	0.0442 (12)	0.0456 (10)	−0.0015 (8)	0.0006 (7)	0.0042 (9)
C15	0.0423 (10)	0.0678 (15)	0.0557 (11)	−0.0129 (10)	0.0009 (8)	0.0091 (11)
C16	0.0419 (10)	0.0437 (12)	0.0471 (10)	−0.0080 (9)	0.0089 (8)	−0.0040 (9)
C17	0.0499 (12)	0.0578 (14)	0.0670 (13)	−0.0009 (10)	0.0136 (10)	0.0003 (11)
C18	0.0641 (14)	0.0630 (16)	0.0935 (18)	−0.0102 (12)	0.0383 (13)	−0.0158 (14)
C19	0.1054 (19)	0.0613 (16)	0.0645 (15)	−0.0224 (14)	0.0406 (14)	−0.0123 (13)
C20	0.0982 (18)	0.0600 (16)	0.0470 (12)	−0.0066 (13)	0.0127 (11)	−0.0033 (11)
C21	0.0598 (12)	0.0527 (13)	0.0483 (11)	0.0012 (10)	0.0073 (9)	−0.0045 (10)

Geometric parameters (Å, º) top

O1—C2	1.223 (2)	C16—C17	1.374 (3)
O2—C9	1.220 (2)	C16—C21	1.380 (3)
N1—N2	1.3787 (19)	C17—C18	1.381 (3)
N1—C12	1.318 (2)	C18—C19	1.377 (3)
N2—C14	1.350 (2)	C19—C20	1.373 (4)
N2—C16	1.429 (2)	C20—C21	1.380 (3)
C1—C2	1.480 (2)	C4—H4	0.9300
C1—C9	1.489 (2)	C5—H5	0.9300
C1—C10	1.351 (2)	C6—H6	0.9300
C2—C3	1.487 (2)	C7—H7	0.9300
C3—C4	1.384 (2)	C10—H10	0.9300
C3—C8	1.388 (2)	C13—H13A	0.9600
C4—C5	1.381 (3)	C13—H13B	0.9600
C5—C6	1.390 (3)	C13—H13C	0.9600
C6—C7	1.379 (3)	C15—H15A	0.9600
C7—C8	1.385 (2)	C15—H15B	0.9600
C8—C9	1.482 (2)	C15—H15C	0.9600
C10—C11	1.434 (2)	C17—H17	0.9300
C11—C12	1.419 (2)	C18—H18	0.9300
C11—C14	1.392 (2)	C19—H19	0.9300
C12—C13	1.493 (2)	C20—H20	0.9300
C14—C15	1.484 (2)	C21—H21	0.9300

N2—N1—C12	104.58 (13)	C17—C18—C19	120.1 (2)
N1—N2—C14	112.65 (13)	C18—C19—C20	120.1 (2)
N1—N2—C16	118.54 (13)	C19—C20—C21	120.3 (2)
C14—N2—C16	128.77 (14)	C16—C21—C20	119.35 (19)
C2—C1—C9	107.17 (14)	C3—C4—H4	121.00
C2—C1—C10	130.24 (16)	C5—C4—H4	121.00
C9—C1—C10	122.11 (15)	C4—C5—H5	120.00
O1—C2—C1	128.67 (16)	C6—C5—H5	120.00
O1—C2—C3	124.66 (16)	C5—C6—H6	119.00
C1—C2—C3	106.57 (14)	C7—C6—H6	119.00
C2—C3—C4	128.51 (16)	C6—C7—H7	121.00
C2—C3—C8	109.87 (14)	C8—C7—H7	121.00
C4—C3—C8	121.62 (16)	C1—C10—H10	115.00
C3—C4—C5	117.97 (17)	C11—C10—H10	115.00
C4—C5—C6	120.46 (18)	C12—C13—H13A	109.00
C5—C6—C7	121.59 (18)	C12—C13—H13B	109.00
C6—C7—C8	118.03 (17)	C12—C13—H13C	109.00
C3—C8—C7	120.32 (16)	H13A—C13—H13B	109.00
C3—C8—C9	109.58 (15)	H13A—C13—H13C	109.00
C7—C8—C9	130.10 (16)	H13B—C13—H13C	109.00
O2—C9—C1	126.67 (16)	C14—C15—H15A	109.00
O2—C9—C8	126.62 (16)	C14—C15—H15B	109.00
C1—C9—C8	106.71 (15)	C14—C15—H15C	109.00
C1—C10—C11	130.99 (16)	H15A—C15—H15B	109.00
C10—C11—C12	125.10 (15)	H15A—C15—H15C	109.00
C10—C11—C14	129.85 (15)	H15B—C15—H15C	109.00
C12—C11—C14	105.00 (15)	C16—C17—H17	120.00
N1—C12—C11	111.71 (14)	C18—C17—H17	120.00
N1—C12—C13	119.87 (15)	C17—C18—H18	120.00
C11—C12—C13	128.37 (16)	C19—C18—H18	120.00
N2—C14—C11	106.01 (14)	C18—C19—H19	120.00
N2—C14—C15	122.38 (15)	C20—C19—H19	120.00
C11—C14—C15	130.47 (15)	C19—C20—H20	120.00
N2—C16—C17	119.90 (16)	C21—C20—H20	120.00
N2—C16—C21	119.37 (16)	C16—C21—H21	120.00
C17—C16—C21	120.70 (17)	C20—C21—H21	120.00
C16—C17—C18	119.49 (19)

C12—N1—N2—C14	−0.43 (19)	C4—C3—C8—C7	0.4 (3)
C12—N1—N2—C16	−178.29 (15)	C4—C3—C8—C9	−179.10 (18)
N2—N1—C12—C11	1.86 (19)	C3—C4—C5—C6	−1.2 (3)
N2—N1—C12—C13	179.52 (16)	C4—C5—C6—C7	0.7 (4)
N1—N2—C14—C11	−1.14 (19)	C5—C6—C7—C8	0.3 (3)
N1—N2—C14—C15	167.82 (16)	C6—C7—C8—C3	−0.8 (3)
C16—N2—C14—C11	176.44 (16)	C6—C7—C8—C9	178.5 (2)
C16—N2—C14—C15	−14.6 (3)	C3—C8—C9—O2	−179.0 (2)
N1—N2—C16—C17	130.59 (19)	C3—C8—C9—C1	1.0 (2)
N1—N2—C16—C21	−47.4 (2)	C7—C8—C9—O2	1.7 (4)
C14—N2—C16—C17	−46.9 (3)	C7—C8—C9—C1	−178.41 (19)
C14—N2—C16—C21	135.2 (2)	C1—C10—C11—C12	−148.87 (18)
C9—C1—C2—O1	−173.0 (2)	C1—C10—C11—C14	34.2 (3)
C9—C1—C2—C3	3.3 (2)	C10—C11—C12—N1	179.86 (16)
C10—C1—C2—O1	−0.9 (4)	C10—C11—C12—C13	2.4 (3)
C10—C1—C2—C3	175.33 (17)	C14—C11—C12—N1	−2.57 (19)
C2—C1—C9—O2	177.3 (2)	C14—C11—C12—C13	−180.00 (19)
C2—C1—C9—C8	−2.7 (2)	C10—C11—C14—N2	179.55 (16)
C10—C1—C9—O2	4.5 (3)	C10—C11—C14—C15	11.8 (3)
C10—C1—C9—C8	−175.48 (16)	C12—C11—C14—N2	2.13 (18)
C2—C1—C10—C11	12.2 (3)	C12—C11—C14—C15	−165.60 (18)
C9—C1—C10—C11	−176.81 (18)	N2—C16—C17—C18	−178.80 (19)
O1—C2—C3—C4	−6.1 (3)	C21—C16—C17—C18	−0.9 (3)
O1—C2—C3—C8	173.65 (19)	N2—C16—C21—C20	178.66 (19)
C1—C2—C3—C4	177.46 (18)	C17—C16—C21—C20	0.7 (3)
C1—C2—C3—C8	−2.8 (2)	C16—C17—C18—C19	0.2 (3)
C2—C3—C4—C5	−179.6 (2)	C17—C18—C19—C20	0.5 (4)
C8—C3—C4—C5	0.7 (3)	C18—C19—C20—C21	−0.7 (4)
C2—C3—C8—C7	−179.42 (18)	C19—C20—C21—C16	0.1 (3)
C2—C3—C8—C9	1.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1ⁱ	0.93	2.58	3.377 (3)	145

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆N₂O₂
M_r	328.36
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	14.6655 (3), 7.8902 (2), 28.6651 (7)
β (°)	98.251 (1)
V (Å³)	3282.61 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.26 × 0.23 × 0.21

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.975, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	12302, 2970, 2106
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.112, 1.01
No. of reflections	2970
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.23

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).