N′-(4-Methoxy­benzyl­idene)methoxy­formohydrazide

Shang, Z.-H.; Zhang, H.-L.; Ding, Y.

doi:10.1107/S160053680703200X

N′-(4-Methoxybenzylidene)methoxyformohydrazide

There are two molecules in the asymmetric unit of the title compound, C₁₀H₁₂N₂O₃, with almost identical conformations. The crystal structure is stabilized by intermolecular N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703200X/hb2470sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680703200X/hb2470Isup2.hkl Contains datablock I

CCDC reference: 658983

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.047
wR factor = 0.144
Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        400 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C9      ..       6.51 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.14
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.31

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          7

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   0 ALERT type 5 Informative message, check

Comment top

Symmetrical and unsymmetrical 1,3,4-oxadiazoles have been reported to be versatile compounds with many properties (Omar et al., 1996; Goswami et al., 1984; Tully et al., 1991; Borg et al., 1999). The most common synthetic approach to 1,3,4-oxadiazoles involves oxidative cyclization from the corresponding aldehyde N-acylhydrazones (Yang & Dai, 1993; Shang, 2006). The title compound, (I), as the oxidative precursor, was synthesized from 4-methoxybenzaldehyde and methyl hydrazinocarboxylate in ethanol under reflux.

Both asymmetric molecules of (I) adopt a trans configuration with respect to the C=N bond (Fig. 1) as discribed previously (Shang et al., 2007). The crystal structure is stabilized mainly through intermolecular N—H··· O hydrogen bonds (Table 1).

Related literature top

For related literature, see: Borg et al. (1999); Goswami et al. (1984); Omar et al. (1996); Shang (2006); Shang et al. (2007); Tully et al. (1991); Yang & Dai (1993).

Experimental top

A mixture of 4-methoxybenzaldehyde (1.36 g, 10 mmol) and methyl hydrazinocarboxylate (0.90 g, 10 mmol) was refluxed in ethanol (30 ml) and monitored by thin-layer chromatography. After the reaction was complete, the resulting solid was filtered off and washed with a little cool methanol. 50 mg of (I) was dissolved in 20 ml e thanol and the solution was kept at room temperature for 10 d; natural evaporation gave colourless prisms of (I) suitable for X-ray analysis.

Structure description top

For related literature, see: Borg et al. (1999); Goswami et al. (1984); Omar et al. (1996); Shang (2006); Shang et al. (2007); Tully et al. (1991); Yang & Dai (1993).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of (I), drawn with 50% probability ellipsoids (arbitrary spheres for the H atoms).
	Fig. 2. Reaction scheme for the formation of the title compound.

N'-(4-Methoxybenzylidene)methoxyformohydrazide top

Crystal data top

C₁₀H₁₂N₂O₃	Z = 4
M_r = 208.22	F(000) = 440
Triclinic, P1	D_x = 1.325 Mg m⁻³
Hall symbol: -P 1	Melting point = 464–466 K
a = 7.3738 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.671 (2) Å	Cell parameters from 1471 reflections
c = 14.689 (3) Å	θ = 2.5–24.6°
α = 89.128 (4)°	µ = 0.10 mm⁻¹
β = 85.961 (4)°	T = 293 K
γ = 87.693 (4)°	Prism, colorless
V = 1044.0 (4) Å³	0.30 × 0.20 × 0.16 mm

Data collection top

Bruker SMART CCD diffractometer	3674 independent reflections
Radiation source: fine-focus sealed tube	2083 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −8→8
T_min = 0.971, T_max = 0.984	k = −9→11
5411 measured reflections	l = −12→17

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0721P)² + 0.0669P] where P = (F_o² + 2F_c²)/3
3674 reflections	(Δ/σ)_max = 0.001
283 parameters	Δρ_max = 0.17 e Å⁻³
7 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₀H₁₂N₂O₃	γ = 87.693 (4)°
M_r = 208.22	V = 1044.0 (4) Å³
Triclinic, P1	Z = 4
a = 7.3738 (16) Å	Mo Kα radiation
b = 9.671 (2) Å	µ = 0.10 mm⁻¹
c = 14.689 (3) Å	T = 293 K
α = 89.128 (4)°	0.30 × 0.20 × 0.16 mm
β = 85.961 (4)°

Data collection top

Bruker SMART CCD diffractometer	3674 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2083 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.984	R_int = 0.025
5411 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	7 restraints
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.17 e Å⁻³
3674 reflections	Δρ_min = −0.18 e Å⁻³
283 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
O1	1.0466 (3)	0.72191 (18)	−0.27347 (12)	0.0742 (6)
O2	0.4251 (3)	0.72508 (15)	0.24793 (12)	0.0739 (6)
O3	0.3898 (3)	0.92926 (15)	0.32026 (11)	0.0672 (5)
O4	0.1151 (3)	0.22590 (17)	0.70570 (12)	0.0740 (6)
O5	0.6009 (2)	0.21963 (15)	0.15450 (11)	0.0613 (5)
O6	0.6331 (2)	0.42596 (15)	0.08266 (11)	0.0609 (5)
N1	0.6155 (3)	0.85722 (18)	0.10837 (13)	0.0511 (5)
N2	0.5379 (3)	0.92379 (19)	0.18515 (14)	0.0543 (5)
N3	0.4456 (3)	0.35778 (19)	0.30239 (13)	0.0538 (5)
N4	0.5092 (3)	0.42285 (19)	0.22325 (14)	0.0554 (6)
C1	1.1315 (5)	0.8106 (3)	−0.34000 (18)	0.0860 (9)
H1A	1.0423	0.8755	−0.3620	0.129*
H1B	1.1851	0.7565	−0.3899	0.129*
H1C	1.2243	0.8598	−0.3131	0.129*
C2	0.9621 (3)	0.7807 (2)	−0.19683 (17)	0.0553 (6)
C3	0.8874 (4)	0.6903 (2)	−0.13273 (18)	0.0636 (7)
H3	0.8954	0.5958	−0.1440	0.076*
C4	0.8010 (3)	0.7373 (2)	−0.05229 (17)	0.0573 (7)
H4	0.7531	0.6744	−0.0094	0.069*
C5	0.7851 (3)	0.8790 (2)	−0.03477 (16)	0.0486 (6)
C6	0.8608 (4)	0.9673 (2)	−0.10001 (17)	0.0598 (7)
H6	0.8516	1.0620	−0.0895	0.072*
C7	0.9497 (4)	0.9210 (2)	−0.18051 (17)	0.0615 (7)
H7	1.0004	0.9834	−0.2229	0.074*
C8	0.6944 (3)	0.9342 (2)	0.04870 (16)	0.0511 (6)
H8	0.6943	1.0289	0.0586	0.061*
C9	0.4497 (4)	0.8480 (2)	0.24991 (17)	0.0543 (6)
C10	0.2883 (4)	0.8629 (3)	0.39364 (19)	0.0823 (9)
H10A	0.1935	0.8119	0.3699	0.123*
H10B	0.2354	0.9315	0.4351	0.123*
H10C	0.3677	0.8008	0.4253	0.123*
C11	0.0553 (4)	0.3160 (3)	0.77846 (17)	0.0767 (8)
H11A	0.1506	0.3770	0.7898	0.115*
H11B	0.0253	0.2623	0.8325	0.115*
H11C	−0.0503	0.3696	0.7621	0.115*
C12	0.1746 (3)	0.2837 (2)	0.62447 (17)	0.0555 (6)
C13	0.1735 (4)	0.4221 (3)	0.60634 (18)	0.0778 (9)
H13	0.1303	0.4850	0.6508	0.093*
C14	0.2377 (5)	0.4679 (3)	0.52072 (19)	0.0879 (10)
H14	0.2366	0.5627	0.5090	0.105*
C15	0.3028 (3)	0.3802 (2)	0.45221 (16)	0.0545 (6)
C16	0.3010 (4)	0.2401 (3)	0.47233 (18)	0.0685 (8)
H16	0.3434	0.1766	0.4281	0.082*
C17	0.2375 (4)	0.1938 (3)	0.55668 (19)	0.0776 (9)
H17	0.2369	0.0991	0.5685	0.093*
C18	0.3728 (4)	0.4349 (2)	0.36433 (16)	0.0616 (7)
H18	0.3635	0.5298	0.3535	0.074*
C19	0.5820 (3)	0.3447 (2)	0.15391 (16)	0.0486 (6)
C20	0.7034 (4)	0.3552 (3)	0.00160 (17)	0.0682 (8)
H20A	0.8084	0.2986	0.0149	0.102*
H20B	0.7369	0.4218	−0.0451	0.102*
H20C	0.6118	0.2978	−0.0192	0.102*
H2A	0.543 (3)	1.0150 (11)	0.1909 (16)	0.073 (8)*
H4A	0.496 (3)	0.5137 (11)	0.2144 (17)	0.075 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0931 (15)	0.0597 (11)	0.0668 (12)	0.0012 (10)	0.0165 (11)	−0.0158 (10)
O2	0.1020 (15)	0.0338 (9)	0.0830 (13)	−0.0088 (9)	0.0193 (11)	−0.0066 (9)
O3	0.0990 (15)	0.0413 (9)	0.0585 (11)	−0.0052 (9)	0.0160 (10)	−0.0047 (8)
O4	0.1010 (15)	0.0564 (11)	0.0617 (11)	−0.0050 (10)	0.0148 (10)	0.0021 (9)
O5	0.0861 (13)	0.0310 (9)	0.0655 (11)	0.0002 (8)	0.0045 (9)	−0.0051 (7)
O6	0.0915 (14)	0.0356 (9)	0.0533 (10)	−0.0021 (8)	0.0115 (9)	−0.0037 (8)
N1	0.0595 (13)	0.0370 (10)	0.0559 (12)	0.0019 (9)	0.0018 (10)	−0.0079 (10)
N2	0.0738 (15)	0.0313 (10)	0.0558 (13)	−0.0009 (10)	0.0090 (11)	−0.0035 (10)
N3	0.0657 (14)	0.0406 (10)	0.0544 (12)	−0.0047 (10)	0.0022 (11)	−0.0034 (10)
N4	0.0786 (16)	0.0330 (11)	0.0526 (12)	−0.0011 (10)	0.0099 (11)	−0.0041 (10)
C1	0.119 (3)	0.077 (2)	0.0587 (17)	0.0095 (18)	0.0152 (18)	−0.0035 (16)
C2	0.0609 (17)	0.0481 (14)	0.0563 (15)	0.0027 (12)	−0.0006 (13)	−0.0108 (12)
C3	0.0767 (19)	0.0371 (13)	0.0752 (18)	−0.0018 (12)	0.0103 (15)	−0.0145 (13)
C4	0.0639 (17)	0.0406 (13)	0.0663 (17)	−0.0026 (12)	0.0065 (13)	−0.0069 (12)
C5	0.0526 (15)	0.0370 (12)	0.0564 (15)	−0.0008 (10)	−0.0041 (12)	−0.0089 (11)
C6	0.0780 (19)	0.0373 (12)	0.0627 (16)	0.0030 (12)	0.0044 (14)	−0.0096 (12)
C7	0.079 (2)	0.0458 (14)	0.0581 (16)	−0.0003 (13)	0.0046 (14)	−0.0001 (12)
C8	0.0645 (17)	0.0321 (11)	0.0563 (15)	−0.0022 (11)	0.0001 (13)	−0.0065 (11)
C9	0.0671 (18)	0.0345 (13)	0.0608 (16)	0.0027 (11)	−0.0032 (13)	−0.0060 (12)
C10	0.106 (2)	0.0636 (17)	0.0737 (19)	−0.0154 (16)	0.0278 (17)	−0.0073 (15)
C11	0.096 (2)	0.0724 (18)	0.0594 (17)	−0.0045 (16)	0.0120 (16)	−0.0027 (15)
C12	0.0641 (17)	0.0472 (14)	0.0548 (15)	−0.0070 (12)	0.0001 (13)	0.0012 (12)
C13	0.122 (3)	0.0487 (16)	0.0600 (17)	−0.0051 (16)	0.0165 (17)	−0.0069 (13)
C14	0.149 (3)	0.0395 (15)	0.0697 (19)	0.0006 (16)	0.028 (2)	0.0000 (14)
C15	0.0658 (18)	0.0406 (13)	0.0562 (15)	−0.0022 (11)	0.0026 (13)	−0.0030 (11)
C16	0.092 (2)	0.0434 (14)	0.0676 (18)	−0.0036 (13)	0.0160 (16)	−0.0083 (13)
C17	0.112 (3)	0.0397 (14)	0.077 (2)	−0.0070 (14)	0.0239 (18)	−0.0012 (14)
C18	0.090 (2)	0.0355 (13)	0.0578 (16)	0.0018 (13)	0.0055 (15)	−0.0027 (12)
C19	0.0584 (17)	0.0338 (12)	0.0539 (15)	−0.0036 (11)	−0.0030 (12)	−0.0043 (11)
C20	0.093 (2)	0.0529 (15)	0.0558 (16)	0.0003 (14)	0.0123 (15)	−0.0101 (13)

Geometric parameters (Å, º) top

O1—C2	1.368 (3)	C5—C6	1.377 (3)
O1—C1	1.419 (3)	C5—C8	1.453 (3)
O2—C9	1.211 (3)	C6—C7	1.383 (3)
O3—C9	1.347 (3)	C6—H6	0.9300
O3—C10	1.427 (3)	C7—H7	0.9300
O4—C12	1.361 (3)	C8—H8	0.9300
O4—C11	1.424 (3)	C10—H10A	0.9600
O5—C19	1.212 (2)	C10—H10B	0.9600
O6—C19	1.341 (3)	C10—H10C	0.9600
O6—C20	1.437 (3)	C11—H11A	0.9600
N1—C8	1.266 (3)	C11—H11B	0.9600
N1—N2	1.384 (3)	C11—H11C	0.9600
N2—C9	1.340 (3)	C12—C13	1.361 (3)
N2—H2A	0.889 (10)	C12—C17	1.375 (3)
N3—C18	1.262 (3)	C13—C14	1.385 (4)
N3—N4	1.375 (3)	C13—H13	0.9300
N4—C19	1.346 (3)	C14—C15	1.373 (3)
N4—H4A	0.889 (10)	C14—H14	0.9300
C1—H1A	0.9600	C15—C16	1.383 (3)
C1—H1B	0.9600	C15—C18	1.456 (3)
C1—H1C	0.9600	C16—C17	1.368 (3)
C2—C3	1.376 (3)	C16—H16	0.9300
C2—C7	1.380 (3)	C17—H17	0.9300
C3—C4	1.376 (3)	C18—H18	0.9300
C3—H3	0.9300	C20—H20A	0.9600
C4—C5	1.397 (3)	C20—H20B	0.9600
C4—H4	0.9300	C20—H20C	0.9600

C2—O1—C1	118.0 (2)	O3—C10—H10A	109.5
C9—O3—C10	116.03 (19)	O3—C10—H10B	109.5
C12—O4—C11	118.09 (19)	H10A—C10—H10B	109.5
C19—O6—C20	115.72 (17)	O3—C10—H10C	109.5
C8—N1—N2	115.66 (18)	H10A—C10—H10C	109.5
C9—N2—N1	118.34 (19)	H10B—C10—H10C	109.5
C9—N2—H2A	120.4 (17)	O4—C11—H11A	109.5
N1—N2—H2A	121.3 (17)	O4—C11—H11B	109.5
C18—N3—N4	116.34 (19)	H11A—C11—H11B	109.5
C19—N4—N3	118.58 (19)	O4—C11—H11C	109.5
C19—N4—H4A	118.6 (17)	H11A—C11—H11C	109.5
N3—N4—H4A	122.7 (17)	H11B—C11—H11C	109.5
O1—C1—H1A	109.5	C13—C12—O4	124.6 (2)
O1—C1—H1B	109.5	C13—C12—C17	118.8 (2)
H1A—C1—H1B	109.5	O4—C12—C17	116.6 (2)
O1—C1—H1C	109.5	C12—C13—C14	119.0 (3)
H1A—C1—H1C	109.5	C12—C13—H13	120.5
H1B—C1—H1C	109.5	C14—C13—H13	120.5
O1—C2—C3	116.0 (2)	C15—C14—C13	123.3 (2)
O1—C2—C7	124.5 (2)	C15—C14—H14	118.4
C3—C2—C7	119.5 (2)	C13—C14—H14	118.4
C2—C3—C4	121.2 (2)	C14—C15—C16	116.5 (2)
C2—C3—H3	119.4	C14—C15—C18	120.7 (2)
C4—C3—H3	119.4	C16—C15—C18	122.8 (2)
C3—C4—C5	120.2 (2)	C17—C16—C15	120.7 (2)
C3—C4—H4	119.9	C17—C16—H16	119.7
C5—C4—H4	119.9	C15—C16—H16	119.7
C6—C5—C4	117.4 (2)	C16—C17—C12	121.8 (2)
C6—C5—C8	120.0 (2)	C16—C17—H17	119.1
C4—C5—C8	122.5 (2)	C12—C17—H17	119.1
C5—C6—C7	122.7 (2)	N3—C18—C15	122.2 (2)
C5—C6—H6	118.6	N3—C18—H18	118.9
C7—C6—H6	118.6	C15—C18—H18	118.9
C2—C7—C6	118.8 (2)	O5—C19—O6	124.1 (2)
C2—C7—H7	120.6	O5—C19—N4	126.0 (2)
C6—C7—H7	120.6	O6—C19—N4	109.86 (19)
N1—C8—C5	122.0 (2)	O6—C20—H20A	109.5
N1—C8—H8	119.0	O6—C20—H20B	109.5
C5—C8—H8	119.0	H20A—C20—H20B	109.5
O2—C9—N2	126.7 (2)	O6—C20—H20C	109.5
O2—C9—O3	123.5 (2)	H20A—C20—H20C	109.5
N2—C9—O3	109.78 (19)	H20B—C20—H20C	109.5

C8—N1—N2—C9	178.8 (2)	C10—O3—C9—N2	178.3 (2)
C18—N3—N4—C19	−177.6 (2)	C11—O4—C12—C13	−3.1 (4)
C1—O1—C2—C3	−177.7 (2)	C11—O4—C12—C17	177.7 (2)
C1—O1—C2—C7	1.6 (4)	O4—C12—C13—C14	−179.9 (3)
O1—C2—C3—C4	179.1 (2)	C17—C12—C13—C14	−0.7 (4)
C7—C2—C3—C4	−0.3 (4)	C12—C13—C14—C15	0.1 (5)
C2—C3—C4—C5	1.0 (4)	C13—C14—C15—C16	0.4 (5)
C3—C4—C5—C6	−0.9 (4)	C13—C14—C15—C18	−178.4 (3)
C3—C4—C5—C8	179.6 (2)	C14—C15—C16—C17	−0.2 (4)
C4—C5—C6—C7	0.1 (4)	C18—C15—C16—C17	178.6 (3)
C8—C5—C6—C7	179.6 (2)	C15—C16—C17—C12	−0.4 (5)
O1—C2—C7—C6	−179.9 (2)	C13—C12—C17—C16	0.9 (5)
C3—C2—C7—C6	−0.5 (4)	O4—C12—C17—C16	−179.8 (2)
C5—C6—C7—C2	0.6 (4)	N4—N3—C18—C15	−178.8 (2)
N2—N1—C8—C5	178.8 (2)	C14—C15—C18—N3	174.7 (3)
C6—C5—C8—N1	176.5 (2)	C16—C15—C18—N3	−4.0 (4)
C4—C5—C8—N1	−4.0 (4)	C20—O6—C19—O5	4.0 (3)
N1—N2—C9—O2	−2.2 (4)	C20—O6—C19—N4	−176.4 (2)
N1—N2—C9—O3	177.75 (19)	N3—N4—C19—O5	−1.4 (4)
C10—O3—C9—O2	−1.8 (4)	N3—N4—C19—O6	178.99 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5ⁱ	0.89 (1)	2.10 (1)	2.940 (2)	158 (2)
N4—H4A···O2	0.89 (1)	2.15 (1)	2.986 (2)	157 (2)

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂N₂O₃
M_r	208.22
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.3738 (16), 9.671 (2), 14.689 (3)
α, β, γ (°)	89.128 (4), 85.961 (4), 87.693 (4)
V (Å³)	1044.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.971, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	5411, 3674, 2083
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.144, 1.00
No. of reflections	3674
No. of parameters	283
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.