5-Benzoyl-4-(4-fluoro­phen­yl)-3,4-dihydro­pyrimidin-2(1H)-one

Kant, R.; Gupta, V.K.; Kapoor, K.; Patil, D.R.; Deshmukh, M.B.

doi:10.1107/S1600536812052105

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o196

doi:10.1107/S1600536812052105

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5-Benzoyl-4-(4-fluorophenyl)-3,4-dihydropyrimidin-2(1H)-one

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a D. R. Patil ^b and Madhukar B. Deshmukh ^b

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^bDepartment of Chemistry, Shivaji University, Kolhapur 416 004(MS), India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 27 December 2012; accepted 31 December 2012; online 9 January 2013)

In the title molecule, C₁₇H₁₃FN₂O₂, the 3,4-dihydropyrimidine ring adopts a flattened sofa conformation with the flap atom (which bears the fluorophenyl substituent) deviating from the plane defined by the remaining five ring atoms by 0.281 (2) Å. This plane forms dihedral angles of 85.98 (6) and 60.63 (6)° with the 4-fluorophenyl and benzoyl-phenyl rings, respectively. The dihedral angle between the 4-fluorophenyl group and the benzene ring is 71.78 (6)°. In the crystal, N—H⋯O hydrogen bonds link molecules into inversion dimers that are further connected by another N—H⋯O interaction into a two-dimensional supramolecular structure parallel to (101).

Related literature

For general background to and pharmaceutical applications of pyrimidinones, see: Ghorab et al. (2000 ); Shivarama Holla et al. (2004 ); Stefani et al. (2006 ). For related structures, see: Fun et al. (2009 ); Chitra et al. (2009 ). For asymmetry parameters, see: Duax & Norton (1975 ).

Experimental

Crystal data

C₁₇H₁₃FN₂O₂
M_r = 296.29
Monoclinic, P 2₁ /n
a = 12.7911 (5) Å
b = 8.1862 (3) Å
c = 13.7325 (5) Å
β = 98.850 (4)°
V = 1420.82 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.777, T_max = 1.000
27552 measured reflections
2786 independent reflections
1836 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.131
S = 1.04
2786 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	1.96	2.777 (2)	159
N3—H3⋯O1ⁱⁱ	0.86	2.12	2.937 (2)	159
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812052105/gk2549sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812052105/gk2549Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812052105/gk2549Isup3.cml

checkCIF report

Comment top

Dihydropyrimidinones exhibit a wide range of biological effects including antifungal, antiviral, anticancer, antibacterial, anti-inflammatory and antihypertensive (Ghorab et al., 2000; Shivarama Holla et al., 2004). Dihydropyrimidin-2(1H)-ones can also be used as antioxidant agents (Stefani et al., 2006). This paper reports the crystal structure of the title dihydropyrimidinone derivative.

In the title compound (Fig.1) all bond lengths and angles are normal and correspond to those observed in related structures (Fun et al., 2009; Chitra et al., 2009). The dihydropyrimidine ring adopts a sofa conformation (ΔC_s(C4) = 5.436)(Duax & Norton, 1975) and the plane of the five essentially coplanar atoms (C5/C6/N1/C2/N3) of this ring (maximum deviation -0.045 (2) Å for all atoms) forms a dihedral angle of 85.98 (6)° and 60.63 (6)° with fluorophenyl and benzene ring respectively. In the crystal, N1—H1···O2 hydrogen bonds link molecules into dimers that are further connected by N3—H3···O1 and (Table 1) interactions into two dimensional supramolecular structure (Fig. 2).

Related literature top

For general background to and pharmaceutical applications of pyrimidinones, see: Ghorab et al. (2000); Shivarama Holla et al. (2004); Stefani et al. (2006). For related structures, see: Fun et al. (2009); Chitra et al. (2009). For asymmetry parameters, see: Duax & Norton (1975).

Experimental top

A mixture of 3-(dimethylamino)-1-phenylprop-2-en-1-one (1mmol), 4-fluorobenzaldehyde (1mmol), urea (1.2 mmol) and PTSA (30 mol%) in 5 ml ethanol was stirred at 78 °C till the completion of the reaction monitored by TLC. Then reaction mixture was gradually cooled down to room temperature. The precipitate was filtered and washed with cold ethanol (m.p.: 555-557 K, yield: 81%). IR(KBr): 3268, 2964,1682, 1641 ,1592, 1371, 1200, 1151 cm^-1;¹H NMR(300 MHz, DMSO-d6): δ = 5.45-5.46(d,1H,CH);7.03-7.14(m,3H,Ar-H); 7.35-7.50(m,6H,Ar-H);7.86-7.87(d,1H,NH); 8.21 ( s,1H,CH ); 9.38 ( s,1H,NH );

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The packing arrangement of molecules viewed along the b axis. The dotted lines show intermolecular N—H···O hydrogen bonds.

5-Benzoyl-4-(4-fluorophenyl)-3,4-dihydropyrimidin-2(1H)-one top

Crystal data top

C₁₇H₁₃FN₂O₂	F(000) = 616
M_r = 296.29	D_x = 1.385 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9924 reflections
a = 12.7911 (5) Å	θ = 3.4–29.0°
b = 8.1862 (3) Å	µ = 0.10 mm⁻¹
c = 13.7325 (5) Å	T = 293 K
β = 98.850 (4)°	Block, colourless
V = 1420.82 (9) Å³	0.3 × 0.2 × 0.2 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2786 independent reflections
Radiation source: fine-focus sealed tube	1836 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.4°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −10→10
T_min = 0.777, T_max = 1.000	l = −16→16
27552 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0593P)² + 0.117P] where P = (F_o² + 2F_c²)/3
2786 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₇H₁₃FN₂O₂	V = 1420.82 (9) Å³
M_r = 296.29	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.7911 (5) Å	µ = 0.10 mm⁻¹
b = 8.1862 (3) Å	T = 293 K
c = 13.7325 (5) Å	0.3 × 0.2 × 0.2 mm
β = 98.850 (4)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2786 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	1836 reflections with I > 2σ(I)
T_min = 0.777, T_max = 1.000	R_int = 0.075
27552 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.04	Δρ_max = 0.21 e Å⁻³
2786 reflections	Δρ_min = −0.14 e Å⁻³
199 parameters

Special details top

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.39760 (11)	0.04963 (17)	0.86034 (11)	0.0532 (4)
O2	0.37270 (12)	0.57074 (18)	0.52393 (11)	0.0584 (5)
F1	0.33786 (14)	0.71433 (18)	1.06679 (11)	0.0932 (5)
N1	0.48454 (13)	0.3865 (2)	0.60718 (13)	0.0497 (5)
H1	0.5352	0.4189	0.5774	0.060*
C2	0.38882 (16)	0.4658 (2)	0.58943 (15)	0.0428 (5)
N3	0.31734 (13)	0.42049 (19)	0.64458 (12)	0.0436 (4)
H3	0.2539	0.4556	0.6267	0.052*
C4	0.33496 (15)	0.3167 (2)	0.73290 (14)	0.0386 (5)
H4	0.2746	0.2422	0.7299	0.046*
C5	0.43279 (15)	0.2146 (2)	0.72997 (14)	0.0383 (5)
C6	0.50143 (16)	0.2583 (2)	0.67049 (15)	0.0429 (5)
H6	0.5635	0.1983	0.6725	0.051*
C7	0.45121 (15)	0.0738 (2)	0.79487 (15)	0.0401 (5)
C8	0.53687 (15)	−0.0452 (2)	0.78012 (15)	0.0406 (5)
C9	0.54036 (17)	−0.1174 (2)	0.68944 (16)	0.0506 (6)
H9	0.4915	−0.0867	0.6352	0.061*
C10	0.61561 (19)	−0.2345 (3)	0.67854 (19)	0.0603 (6)
H10	0.6164	−0.2836	0.6176	0.072*
C11	0.6889 (2)	−0.2778 (3)	0.7576 (2)	0.0674 (7)
H11	0.7398	−0.3562	0.7503	0.081*
C12	0.68740 (19)	−0.2060 (3)	0.8473 (2)	0.0642 (7)
H12	0.7382	−0.2348	0.9005	0.077*
C13	0.61117 (18)	−0.0912 (2)	0.85984 (17)	0.0502 (6)
H13	0.6098	−0.0450	0.9215	0.060*
C14	0.33820 (15)	0.4208 (2)	0.82489 (14)	0.0374 (5)
C15	0.41687 (18)	0.5364 (3)	0.85035 (16)	0.0507 (6)
H15	0.4704	0.5474	0.8120	0.061*
C16	0.4170 (2)	0.6356 (3)	0.93181 (17)	0.0598 (6)
H16	0.4698	0.7131	0.9485	0.072*
C17	0.3384 (2)	0.6174 (3)	0.98687 (17)	0.0578 (6)
C18	0.2588 (2)	0.5067 (3)	0.96424 (17)	0.0582 (6)
H18	0.2049	0.4986	1.0024	0.070*
C19	0.26005 (17)	0.4065 (2)	0.88326 (16)	0.0480 (5)
H19	0.2073	0.3283	0.8680	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0473 (9)	0.0574 (9)	0.0592 (9)	0.0000 (7)	0.0219 (8)	0.0136 (7)
O2	0.0593 (10)	0.0675 (10)	0.0529 (9)	0.0202 (8)	0.0223 (8)	0.0227 (8)
F1	0.1272 (14)	0.0846 (10)	0.0730 (10)	−0.0053 (10)	0.0323 (10)	−0.0299 (8)
N1	0.0388 (10)	0.0546 (10)	0.0600 (11)	0.0094 (8)	0.0215 (9)	0.0197 (9)
C2	0.0419 (12)	0.0473 (12)	0.0407 (11)	0.0065 (9)	0.0113 (9)	0.0021 (10)
N3	0.0329 (9)	0.0572 (10)	0.0415 (9)	0.0100 (8)	0.0084 (8)	0.0092 (8)
C4	0.0318 (11)	0.0403 (10)	0.0454 (11)	0.0005 (8)	0.0114 (9)	0.0059 (9)
C5	0.0333 (11)	0.0390 (10)	0.0434 (11)	0.0007 (8)	0.0085 (9)	0.0023 (9)
C6	0.0356 (11)	0.0436 (11)	0.0510 (12)	0.0056 (9)	0.0113 (10)	0.0075 (9)
C7	0.0352 (11)	0.0398 (10)	0.0457 (12)	−0.0046 (9)	0.0076 (9)	0.0013 (9)
C8	0.0356 (11)	0.0356 (10)	0.0518 (12)	−0.0036 (9)	0.0104 (9)	0.0043 (9)
C9	0.0443 (13)	0.0534 (13)	0.0539 (14)	−0.0003 (10)	0.0068 (11)	−0.0008 (10)
C10	0.0544 (15)	0.0568 (14)	0.0713 (17)	0.0000 (12)	0.0145 (13)	−0.0135 (12)
C11	0.0524 (16)	0.0509 (14)	0.099 (2)	0.0110 (11)	0.0109 (15)	−0.0053 (14)
C12	0.0471 (15)	0.0578 (14)	0.0825 (18)	0.0111 (12)	−0.0063 (13)	0.0104 (13)
C13	0.0499 (14)	0.0440 (12)	0.0548 (13)	−0.0032 (10)	0.0022 (11)	0.0048 (10)
C14	0.0361 (11)	0.0353 (10)	0.0418 (11)	0.0028 (9)	0.0089 (9)	0.0067 (8)
C15	0.0477 (14)	0.0549 (13)	0.0522 (13)	−0.0060 (10)	0.0160 (11)	0.0003 (10)
C16	0.0679 (17)	0.0523 (13)	0.0589 (14)	−0.0110 (12)	0.0091 (13)	−0.0048 (12)
C17	0.0790 (18)	0.0484 (13)	0.0480 (13)	0.0049 (12)	0.0159 (12)	−0.0062 (11)
C18	0.0688 (17)	0.0569 (14)	0.0566 (14)	0.0052 (12)	0.0346 (13)	0.0029 (12)
C19	0.0468 (13)	0.0436 (12)	0.0571 (13)	−0.0019 (9)	0.0190 (11)	0.0030 (10)

Geometric parameters (Å, º) top

O1—C7	1.228 (2)	C9—H9	0.9300
O2—C2	1.238 (2)	C10—C11	1.367 (3)
F1—C17	1.355 (2)	C10—H10	0.9300
N1—C6	1.359 (2)	C11—C12	1.369 (3)
N1—C2	1.374 (3)	C11—H11	0.9300
N1—H1	0.8600	C12—C13	1.384 (3)
C2—N3	1.327 (2)	C12—H12	0.9300
N3—C4	1.470 (2)	C13—H13	0.9300
N3—H3	0.8600	C14—C19	1.379 (3)
C4—C5	1.511 (3)	C14—C15	1.387 (3)
C4—C14	1.519 (3)	C15—C16	1.382 (3)
C4—H4	0.9800	C15—H15	0.9300
C5—C6	1.337 (3)	C16—C17	1.356 (3)
C5—C7	1.454 (3)	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.362 (3)
C7—C8	1.503 (3)	C18—C19	1.384 (3)
C8—C9	1.385 (3)	C18—H18	0.9300
C8—C13	1.387 (3)	C19—H19	0.9300
C9—C10	1.383 (3)

C6—N1—C2	121.89 (17)	C11—C10—C9	119.9 (2)
C6—N1—H1	119.1	C11—C10—H10	120.1
C2—N1—H1	119.1	C9—C10—H10	120.1
O2—C2—N3	123.82 (18)	C10—C11—C12	120.0 (2)
O2—C2—N1	120.08 (18)	C10—C11—H11	120.0
N3—C2—N1	116.09 (17)	C12—C11—H11	120.0
C2—N3—C4	126.95 (16)	C11—C12—C13	120.7 (2)
C2—N3—H3	116.5	C11—C12—H12	119.6
C4—N3—H3	116.5	C13—C12—H12	119.6
N3—C4—C5	108.69 (15)	C12—C13—C8	119.8 (2)
N3—C4—C14	110.09 (14)	C12—C13—H13	120.1
C5—C4—C14	114.58 (16)	C8—C13—H13	120.1
N3—C4—H4	107.7	C19—C14—C15	118.29 (19)
C5—C4—H4	107.7	C19—C14—C4	120.43 (18)
C14—C4—H4	107.7	C15—C14—C4	121.23 (17)
C6—C5—C7	121.81 (17)	C16—C15—C14	121.0 (2)
C6—C5—C4	119.51 (17)	C16—C15—H15	119.5
C7—C5—C4	118.64 (16)	C14—C15—H15	119.5
C5—C6—N1	122.90 (18)	C17—C16—C15	118.6 (2)
C5—C6—H6	118.6	C17—C16—H16	120.7
N1—C6—H6	118.6	C15—C16—H16	120.7
O1—C7—C5	121.36 (17)	F1—C17—C16	118.9 (2)
O1—C7—C8	119.69 (17)	F1—C17—C18	118.5 (2)
C5—C7—C8	118.95 (17)	C16—C17—C18	122.5 (2)
C9—C8—C13	118.75 (19)	C17—C18—C19	118.5 (2)
C9—C8—C7	121.50 (19)	C17—C18—H18	120.7
C13—C8—C7	119.67 (19)	C19—C18—H18	120.7
C10—C9—C8	120.8 (2)	C14—C19—C18	121.0 (2)
C10—C9—H9	119.6	C14—C19—H19	119.5
C8—C9—H9	119.6	C18—C19—H19	119.5

C6—N1—C2—O2	−172.51 (19)	C7—C8—C9—C10	−175.79 (18)
C6—N1—C2—N3	6.3 (3)	C8—C9—C10—C11	−1.2 (3)
O2—C2—N3—C4	−169.86 (18)	C9—C10—C11—C12	0.3 (4)
N1—C2—N3—C4	11.4 (3)	C10—C11—C12—C13	1.1 (4)
C2—N3—C4—C5	−22.5 (3)	C11—C12—C13—C8	−1.5 (3)
C2—N3—C4—C14	103.8 (2)	C9—C8—C13—C12	0.6 (3)
N3—C4—C5—C6	17.7 (3)	C7—C8—C13—C12	177.22 (19)
C14—C4—C5—C6	−105.9 (2)	N3—C4—C14—C19	113.42 (19)
N3—C4—C5—C7	−164.33 (16)	C5—C4—C14—C19	−123.7 (2)
C14—C4—C5—C7	72.1 (2)	N3—C4—C14—C15	−64.1 (2)
C7—C5—C6—N1	178.06 (18)	C5—C4—C14—C15	58.8 (2)
C4—C5—C6—N1	−4.0 (3)	C19—C14—C15—C16	−0.3 (3)
C2—N1—C6—C5	−9.6 (3)	C4—C14—C15—C16	177.24 (19)
C6—C5—C7—O1	167.94 (19)	C14—C15—C16—C17	0.1 (3)
C4—C5—C7—O1	−10.0 (3)	C15—C16—C17—F1	−179.9 (2)
C6—C5—C7—C8	−12.9 (3)	C15—C16—C17—C18	−0.8 (4)
C4—C5—C7—C8	169.22 (17)	F1—C17—C18—C19	−179.3 (2)
O1—C7—C8—C9	125.5 (2)	C16—C17—C18—C19	1.6 (4)
C5—C7—C8—C9	−53.7 (2)	C15—C14—C19—C18	1.1 (3)
O1—C7—C8—C13	−51.0 (3)	C4—C14—C19—C18	−176.45 (18)
C5—C7—C8—C13	129.8 (2)	C17—C18—C19—C14	−1.7 (3)
C13—C8—C9—C10	0.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	1.96	2.777 (2)	159
N3—H3···O1ⁱⁱ	0.86	2.12	2.937 (2)	159

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃FN₂O₂
M_r	296.29
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	12.7911 (5), 8.1862 (3), 13.7325 (5)
β (°)	98.850 (4)
V (Å³)	1420.82 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.777, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	27552, 2786, 1836
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.131, 1.04
No. of reflections	2786
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.14

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	1.96	2.777 (2)	159
N3—H3···O1ⁱⁱ	0.86	2.12	2.937 (2)	159

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

Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

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