3,5-Bis(2,4-dinitro­phen­yl)-4-nitro-1H-pyrazole acetone monosolvate

Mathivathanan, L.

doi:10.1107/S1600536812001146

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o411

doi:10.1107/S1600536812001146

Open

access

3,5-Bis(2,4-dinitrophenyl)-4-nitro-1H-pyrazole acetone monosolvate

Logesh Mathivathanan ^a ^*

^aDeparment of Chemistry, University of Puerto Rico – Rio Piedras, San Juan, PR 00936, USA
^*Correspondence e-mail: mathivathanan.logesh@gmail.com

(Received 17 October 2011; accepted 10 January 2012; online 14 January 2012)

The title structure, C₁₅H₇N₇O₁₀·C₃H₆O, was prepared by pentanitration of 3,5-diphenyl-1H-pyrazole. The proton attached to a pyrazole N atom forms a hydrogen bond with the O atom of the acetone solvent molecule, owing to the NO₂ enhanced acidity of the proton. The NO₂ group on the phenyl C atom is twisted by 33.9 (2)° from coplanarity with the ring in order to avoid a short intramolecular O⋯O contact with an O atom of an adjacent pyrazole-bonded NO₂ group.

Related literature

For the nitration of 1H-pyrazole, see: Maresca et al. (1997 ). For the crystal structure of 3,5-diphenyl-1H-pyrazole, which shows a hydrogen-bonded tetrameric structure, see: Raptis et al. (1993 ). For a crystallographic and ab initio study of 1H-pyrazoles, see: Foces-Foces et al. (2000 ).

Experimental

Crystal data

C₁₅H₇N₇O₁₀·C₃H₆O
M_r = 503.35
Monoclinic, P 2₁ /c
a = 14.886 (10) Å
b = 7.678 (5) Å
c = 19.801 (13) Å
β = 104.944 (9)°
V = 2187 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 298 K
0.31 × 0.19 × 0.18 mm

Data collection

Bruker SMART 1K CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.836, T_max = 0.977
15182 measured reflections
5041 independent reflections
2703 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.202
S = 1.03
5041 reflections
332 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O11ⁱ	0.92 (3)	1.87 (4)	2.786 (4)	177 (3)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812001146/qk2027sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001146/qk2027Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812001146/qk2027Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812001146/qk2027Isup4.cml

checkCIF report

Comment top

Aromatic electrophilic nitration (Maresca et al., 1997) of 3,5-diphenyl-1H-pyrazole using nitration mixture (H₂SO₄/HNO₃) produces the title compound, 3,5-bis-(2,4-dinitrophenyl)-4-nitro-1H-pyrazole. The crystal structure of the parent 3,5-diphenyl-1H-pyrazole is a H-bonded tetrameric structure (Raptis et al., 1993), while the title compound (I) is not. Poly-nitration, in addition to a H-bonding to the solvent acetone molecule prevents tetramer formation in (I) (Fig. 1). H-bonding induced supramolecular network formation in 1H-pyrazoles has been summarized by Foces-Foces et al. (2000).

An intermolecular dipole-dipole interaction makes N4 and O2(1-x, y-1/2, 1/2-z) lie at 2.89 Å. In (I), all the NO₂-groups are coplanar or nearly coplanar to their carrier rings, except the one attached to C5, which is twisted by 33.9 (2) relative to the phenyl ring in order to avoid a short intramolecular contact with O2.

Related literature top

For the nitration of 1H-pyrazole, see: Maresca et al. (1997). For the crystal structure of 3,5-diphenyl-1H-pyrazole, which shows a hydrogen-bonded tetrameric structure, see: Raptis et al. (1993). For a crystallographic and ab initio study of 1H-pyrazoles, see: Foces-Foces et al. (2000).

Experimental top

For a general procedure for nitration of pyrazole, see Maresca et al. (1997). A flask containing 5 ml of conc. H₂SO₄ and 5 ml HNO₃ kept in an ice bath was charged with 3,5-diphenyl-1H-pyrazole (97%, Aldrich; 2.0 g, 9.07 mmol) followed by the addition of 10 ml of H₂SO₄. The mixture was heated at 110° C for 2 days. After conventional neutralization and extractions, several colourless crystals of the title compound (I) were obtained from acetone.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound (I) showing 30% thermal ellipsoids and atom labeling scheme. The symmetry transformation for the shown acetone molecule is x, 1/2-y, z-1/2.

3,5-Bis(2,4-dinitrophenyl)-4-nitro-1H-pyrazole acetone monosolvate top

Crystal data top

C₁₅H₇N₇O₁₀·C₃H₆O	F(000) = 1032
M_r = 503.35	D_x = 1.529 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5811 reflections
a = 14.886 (10) Å	θ = 2.1–27.1°
b = 7.678 (5) Å	µ = 0.13 mm⁻¹
c = 19.801 (13) Å	T = 298 K
β = 104.944 (9)°	Polygon, colourless
V = 2187 (2) Å³	0.31 × 0.19 × 0.18 mm
Z = 4

Data collection top

Bruker SMART 1K CCD diffractometer	5041 independent reflections
Radiation source: fine-focus sealed tube	2703 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ϕ and ω scans	θ_max = 28.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→18
T_min = 0.836, T_max = 0.977	k = −10→8
15182 measured reflections	l = −25→25

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.202	w = 1/[σ²(F_o²) + (0.0696P)² + 1.6838P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.005
5041 reflections	Δρ_max = 0.27 e Å⁻³
332 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0141 (17)

Crystal data top

C₁₅H₇N₇O₁₀·C₃H₆O	V = 2187 (2) Å³
M_r = 503.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.886 (10) Å	µ = 0.13 mm⁻¹
b = 7.678 (5) Å	T = 298 K
c = 19.801 (13) Å	0.31 × 0.19 × 0.18 mm
β = 104.944 (9)°

Data collection top

Bruker SMART 1K CCD diffractometer	5041 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2703 reflections with I > 2σ(I)
T_min = 0.836, T_max = 0.977	R_int = 0.068
15182 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.202	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.27 e Å⁻³
5041 reflections	Δρ_min = −0.27 e Å⁻³
332 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	0.47956 (18)	−0.0956 (4)	0.26917 (13)	0.0968 (10)
O2	0.59247 (15)	−0.0052 (4)	0.22802 (11)	0.0746 (7)
O3	0.55406 (17)	−0.1803 (3)	0.08688 (13)	0.0730 (7)
O4	0.70324 (18)	−0.1641 (3)	0.12926 (15)	0.0868 (8)
O5	0.82468 (17)	0.3068 (4)	0.00361 (16)	0.0910 (9)
O6	0.7904 (2)	0.5619 (4)	0.03522 (18)	0.1034 (10)
O7	0.3592 (2)	−0.3312 (4)	0.12047 (15)	0.0919 (8)
O8	0.2556 (2)	−0.5123 (4)	0.13596 (16)	0.1052 (10)
O9	0.0670 (4)	−0.3824 (9)	0.2888 (3)	0.205 (3)
O10	0.0655 (3)	−0.1292 (9)	0.3325 (2)	0.187 (3)
O11	0.13846 (15)	0.4236 (3)	0.49406 (14)	0.0766 (7)
N1	0.38256 (16)	0.1537 (3)	0.05753 (13)	0.0565 (6)
N2	0.31564 (17)	0.0836 (4)	0.08520 (13)	0.0575 (7)
N3	0.0923 (3)	−0.2335 (10)	0.2962 (2)	0.1284 (19)
N4	0.2938 (2)	−0.3698 (4)	0.14388 (16)	0.0764 (8)
N5	0.6270 (2)	−0.1003 (3)	0.10191 (14)	0.0612 (7)
N6	0.77797 (18)	0.4055 (4)	0.02940 (16)	0.0678 (7)
N7	0.50947 (19)	−0.0255 (4)	0.22360 (13)	0.0632 (7)
C1	0.46197 (19)	0.1219 (4)	0.10473 (14)	0.0471 (6)
C2	0.44426 (18)	0.0326 (4)	0.16222 (14)	0.0490 (7)
C3	0.34937 (19)	0.0095 (4)	0.14748 (14)	0.0509 (7)
C4	0.54864 (18)	0.1890 (4)	0.09021 (13)	0.0471 (6)
C5	0.62536 (19)	0.0882 (4)	0.08719 (14)	0.0480 (6)
C6	0.70118 (19)	0.1549 (4)	0.06789 (15)	0.0531 (7)
H6	0.7512	0.0847	0.0656	0.064*
C7	0.69967 (19)	0.3305 (4)	0.05218 (15)	0.0521 (7)
C8	0.6277 (2)	0.4380 (4)	0.05695 (16)	0.0563 (7)
H8	0.6295	0.5564	0.0474	0.068*
C9	0.5529 (2)	0.3668 (4)	0.07611 (15)	0.0535 (7)
H9	0.5041	0.4388	0.0798	0.064*
C10	0.2870 (2)	−0.0633 (5)	0.18751 (15)	0.0578 (8)
C11	0.2586 (2)	−0.2379 (5)	0.18530 (16)	0.0624 (8)
C12	0.1955 (2)	−0.2936 (6)	0.22124 (18)	0.0798 (11)
H12	0.1764	−0.4093	0.2193	0.096*
C13	0.1618 (2)	−0.1736 (7)	0.25983 (19)	0.0853 (13)
C14	0.1888 (3)	−0.0032 (7)	0.2649 (2)	0.0913 (13)
H14	0.1658	0.0744	0.2924	0.110*
C15	0.2510 (3)	0.0513 (6)	0.2283 (2)	0.0812 (11)
H15	0.2694	0.1674	0.2310	0.097*
C16	0.0075 (3)	0.2910 (6)	0.4196 (2)	0.0893 (12)
H16A	0.0173	0.3761	0.3867	0.134*
H16B	−0.0549	0.3008	0.4244	0.134*
H16C	0.0168	0.1764	0.4032	0.134*
C17	0.0743 (2)	0.3214 (4)	0.48844 (18)	0.0609 (8)
C18	0.0603 (3)	0.2265 (6)	0.5498 (2)	0.0834 (11)
H18A	0.0700	0.1042	0.5444	0.125*
H18B	−0.0019	0.2454	0.5536	0.125*
H18C	0.1038	0.2681	0.5913	0.125*
H2A	0.256 (2)	0.082 (5)	0.0567 (18)	0.075 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0783 (17)	0.142 (3)	0.0701 (16)	−0.0068 (17)	0.0195 (13)	0.0425 (16)
O2	0.0506 (13)	0.108 (2)	0.0623 (13)	0.0001 (12)	0.0096 (10)	0.0091 (12)
O3	0.0783 (16)	0.0507 (13)	0.1029 (18)	−0.0055 (12)	0.0467 (14)	−0.0059 (12)
O4	0.0821 (17)	0.0677 (16)	0.114 (2)	0.0257 (14)	0.0310 (15)	0.0248 (14)
O5	0.0710 (16)	0.0891 (19)	0.131 (2)	0.0153 (14)	0.0578 (16)	0.0194 (17)
O6	0.100 (2)	0.0686 (18)	0.162 (3)	−0.0261 (16)	0.069 (2)	−0.0075 (18)
O7	0.108 (2)	0.0742 (18)	0.106 (2)	−0.0130 (16)	0.0497 (18)	−0.0134 (15)
O8	0.124 (2)	0.0762 (19)	0.103 (2)	−0.0379 (18)	0.0081 (18)	−0.0121 (15)
O9	0.189 (5)	0.263 (7)	0.197 (5)	−0.123 (5)	0.111 (4)	0.003 (4)
O10	0.159 (4)	0.299 (7)	0.145 (4)	−0.057 (4)	0.116 (3)	−0.024 (4)
O11	0.0555 (13)	0.0701 (15)	0.0989 (18)	−0.0122 (12)	0.0104 (12)	0.0034 (13)
N1	0.0487 (13)	0.0669 (16)	0.0573 (14)	0.0051 (12)	0.0197 (11)	0.0084 (12)
N2	0.0440 (13)	0.0720 (18)	0.0573 (14)	0.0031 (12)	0.0145 (12)	0.0073 (12)
N3	0.082 (3)	0.223 (6)	0.088 (3)	−0.044 (3)	0.036 (2)	0.024 (3)
N4	0.085 (2)	0.069 (2)	0.0689 (18)	−0.0151 (17)	0.0088 (16)	0.0013 (15)
N5	0.0655 (17)	0.0499 (15)	0.0749 (17)	0.0105 (14)	0.0305 (14)	0.0040 (12)
N6	0.0544 (15)	0.069 (2)	0.0849 (19)	−0.0030 (14)	0.0275 (14)	0.0056 (15)
N7	0.0565 (15)	0.0789 (19)	0.0539 (14)	−0.0019 (13)	0.0134 (12)	0.0097 (13)
C1	0.0482 (15)	0.0452 (15)	0.0502 (14)	0.0015 (12)	0.0168 (12)	−0.0008 (11)
C2	0.0481 (15)	0.0528 (17)	0.0472 (14)	0.0007 (12)	0.0143 (12)	0.0030 (12)
C3	0.0504 (16)	0.0543 (17)	0.0508 (15)	0.0001 (13)	0.0182 (12)	0.0013 (12)
C4	0.0461 (14)	0.0479 (15)	0.0485 (14)	0.0028 (12)	0.0140 (12)	−0.0001 (11)
C5	0.0493 (15)	0.0420 (15)	0.0543 (15)	0.0060 (12)	0.0163 (12)	0.0016 (12)
C6	0.0470 (15)	0.0532 (17)	0.0608 (17)	0.0090 (13)	0.0167 (13)	0.0000 (13)
C7	0.0443 (15)	0.0521 (17)	0.0617 (17)	−0.0024 (13)	0.0171 (13)	−0.0002 (13)
C8	0.0584 (17)	0.0437 (15)	0.0699 (18)	0.0006 (14)	0.0224 (15)	−0.0004 (13)
C9	0.0545 (16)	0.0461 (16)	0.0637 (17)	0.0062 (13)	0.0221 (14)	0.0014 (13)
C10	0.0495 (16)	0.070 (2)	0.0552 (16)	−0.0024 (15)	0.0162 (13)	0.0050 (14)
C11	0.0522 (17)	0.075 (2)	0.0559 (17)	−0.0110 (16)	0.0071 (14)	0.0053 (15)
C12	0.064 (2)	0.103 (3)	0.067 (2)	−0.030 (2)	0.0062 (17)	0.015 (2)
C13	0.058 (2)	0.140 (4)	0.062 (2)	−0.020 (2)	0.0228 (17)	0.011 (2)
C14	0.078 (3)	0.129 (4)	0.080 (3)	−0.006 (3)	0.044 (2)	−0.004 (2)
C15	0.079 (2)	0.093 (3)	0.085 (2)	−0.003 (2)	0.047 (2)	−0.007 (2)
C16	0.071 (2)	0.094 (3)	0.094 (3)	−0.009 (2)	0.006 (2)	−0.009 (2)
C17	0.0443 (16)	0.0538 (18)	0.084 (2)	0.0033 (14)	0.0152 (15)	−0.0014 (15)
C18	0.070 (2)	0.090 (3)	0.094 (3)	−0.002 (2)	0.028 (2)	0.006 (2)

Geometric parameters (Å, º) top

O1—N7	1.228 (3)	C4—C9	1.398 (4)
O2—N7	1.226 (3)	C5—C6	1.380 (4)
O3—N5	1.216 (3)	C6—C7	1.382 (4)
O4—N5	1.226 (3)	C6—H6	0.9300
O5—N6	1.225 (4)	C7—C8	1.375 (4)
O6—N6	1.216 (4)	C8—C9	1.378 (4)
O7—N4	1.218 (4)	C8—H8	0.9300
O8—N4	1.224 (4)	C9—H9	0.9300
O9—N3	1.200 (8)	C10—C15	1.391 (5)
O10—N3	1.209 (7)	C10—C11	1.402 (5)
O11—C17	1.219 (4)	C11—C12	1.385 (5)
N1—C1	1.327 (4)	C12—C13	1.372 (6)
N1—N2	1.365 (3)	C12—H12	0.9300
N2—C3	1.333 (4)	C13—C14	1.365 (6)
N2—H2A	0.92 (3)	C14—C15	1.380 (5)
N3—C13	1.480 (5)	C14—H14	0.9300
N4—C11	1.481 (5)	C15—H15	0.9300
N5—C5	1.476 (4)	C16—C17	1.484 (5)
N6—C7	1.471 (4)	C16—H16A	0.9600
N7—C2	1.418 (4)	C16—H16B	0.9600
C1—C2	1.411 (4)	C16—H16C	0.9600
C1—C4	1.485 (4)	C17—C18	1.477 (5)
C2—C3	1.378 (4)	C18—H18A	0.9600
C3—C10	1.478 (4)	C18—H18B	0.9600
C4—C5	1.394 (4)	C18—H18C	0.9600

C1—N1—N2	104.7 (2)	C7—C8—C9	118.7 (3)
C3—N2—N1	113.6 (2)	C7—C8—H8	120.7
C3—N2—H2A	130 (2)	C9—C8—H8	120.7
N1—N2—H2A	116 (2)	C8—C9—C4	121.6 (3)
O9—N3—O10	124.3 (5)	C8—C9—H9	119.2
O9—N3—C13	118.2 (6)	C4—C9—H9	119.2
O10—N3—C13	117.5 (6)	C15—C10—C11	117.7 (3)
O7—N4—O8	124.0 (4)	C15—C10—C3	117.4 (3)
O7—N4—C11	118.4 (3)	C11—C10—C3	124.8 (3)
O8—N4—C11	117.6 (3)	C12—C11—C10	121.2 (4)
O3—N5—O4	125.0 (3)	C12—C11—N4	117.2 (3)
O3—N5—C5	118.6 (3)	C10—C11—N4	121.6 (3)
O4—N5—C5	116.4 (3)	C13—C12—C11	118.2 (4)
O6—N6—O5	124.1 (3)	C13—C12—H12	120.9
O6—N6—C7	118.1 (3)	C11—C12—H12	120.9
O5—N6—C7	117.7 (3)	C14—C13—C12	122.9 (3)
O2—N7—O1	123.6 (3)	C14—C13—N3	119.5 (5)
O2—N7—C2	118.4 (2)	C12—C13—N3	117.7 (5)
O1—N7—C2	118.0 (3)	C13—C14—C15	118.4 (4)
N1—C1—C2	109.9 (2)	C13—C14—H14	120.8
N1—C1—C4	117.4 (2)	C15—C14—H14	120.8
C2—C1—C4	132.7 (2)	C14—C15—C10	121.6 (4)
C3—C2—C1	106.6 (2)	C14—C15—H15	119.2
C3—C2—N7	125.4 (3)	C10—C15—H15	119.2
C1—C2—N7	128.0 (3)	C17—C16—H16A	109.5
N2—C3—C2	105.2 (2)	C17—C16—H16B	109.5
N2—C3—C10	121.2 (3)	H16A—C16—H16B	109.5
C2—C3—C10	133.4 (3)	C17—C16—H16C	109.5
C5—C4—C9	117.0 (3)	H16A—C16—H16C	109.5
C5—C4—C1	125.3 (3)	H16B—C16—H16C	109.5
C9—C4—C1	117.7 (2)	O11—C17—C18	121.1 (3)
C6—C5—C4	122.9 (3)	O11—C17—C16	120.6 (3)
C6—C5—N5	116.5 (2)	C18—C17—C16	118.4 (3)
C4—C5—N5	120.6 (2)	C17—C18—H18A	109.5
C5—C6—C7	117.2 (3)	C17—C18—H18B	109.5
C5—C6—H6	121.4	H18A—C18—H18B	109.5
C7—C6—H6	121.4	C17—C18—H18C	109.5
C8—C7—C6	122.5 (3)	H18A—C18—H18C	109.5
C8—C7—N6	118.6 (3)	H18B—C18—H18C	109.5
C6—C7—N6	118.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O11ⁱ	0.92 (3)	1.87 (4)	2.786 (4)	177 (3)

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₇N₇O₁₀·C₃H₆O
M_r	503.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	14.886 (10), 7.678 (5), 19.801 (13)
β (°)	104.944 (9)
V (Å³)	2187 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.31 × 0.19 × 0.18

Data collection
Diffractometer	Bruker SMART 1K CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.836, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	15182, 5041, 2703
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.202, 1.03
No. of reflections	5041
No. of parameters	332
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.27

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O11ⁱ	0.92 (3)	1.87 (4)	2.786 (4)	177 (3)

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

The author thanks IFN-EPSCoR at the University of Puerto Rico for a graduate fellowship and Dr Raphael G. Raptis for his comments and for the use of X-ray facilities.

References

Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Foces-Foces, C., Alkorta, I. & Elguero, J. (2000). Acta Cryst. B56, 1018–1028. Web of Science CrossRef CAS IUCr Journals Google Scholar
Maresca, K. P., Rose, D. J. & Zubieta, J. (1997). Inorg. Chim. Acta, 260, 83–88. CSD CrossRef CAS Web of Science Google Scholar
Raptis, R. G., Staples, R. J., King, C. & Fackler, J. P. (1993). Acta Cryst. C49, 1716–1719. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar