1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-aminium bromide monohydrate

Yang, Y.-Y.; Xu, L.; Kang, T.-G.; Chen, T.; Wu, P.

doi:10.1107/S1600536812023550

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1964

doi:10.1107/S1600536812023550

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1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-aminium bromide monohydrate

Yan-Yun Yang,^a Liang Xu,^a ^* Ting-Guo Kang,^a Ting Chen ^a and Ping Wu ^a

^aLiaoning University of Traditional Chinese Medicine, Dalian 116600, People's Republic of China
^*Correspondence e-mail: lnzyxuliang@eyou.com

(Received 15 May 2012; accepted 23 May 2012; online 31 May 2012)

In the title hydrated molecular salt, C₁₁H₁₄N₃O⁺·Br⁻·H₂O, the Br⁻ anion is split and appears as two independent half-occupied Br⁻ anions on twofold rotation axes. The dihedral angle between the phenyl ring and the mean plane of the 2,3-dihydro-1H-pyrazole ring (r.m.s. devation = 0.014 Å) is 62.43 (7)°. In the crystal, the components are connected via O—H⋯Br and N—H⋯O hydrogen bonds to form a one-dimensional polymeric structure propagating along [001].

Related literature

For general background on pyrazolone derivatives, see: Casas et al. (2007 ); Jain et al. (2003 ); Zhang et al. (2008 ). For related structures, see: Chitradevi et al. (2009 ); Murtaza et al.(2011 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₄N₃O⁺·Br⁻·H₂O
M_r = 302.17
Monoclinic, C 2/c
a = 14.9080 (19) Å
b = 15.3961 (19) Å
c = 11.1501 (14) Å
β = 93.657 (2)°
V = 2554.0 (6) Å³
Z = 8
Mo Kα radiation
μ = 3.21 mm⁻¹
T = 296 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.489, T_max = 0.556
11995 measured reflections
3222 independent reflections
2081 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.108
S = 1.04
3222 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯Br1	0.85	2.51	3.360 (2)	173
O1W—H1WB⋯Br2	0.85	2.52	3.371 (3)	173
N3—H3B⋯O1ⁱ	0.89	1.89	2.692 (3)	150
N3—H3C⋯O1W	0.89	2.55	3.321 (3)	146
N3—H3C⋯O1ⁱⁱ	0.89	2.37	3.004 (3)	129
N3—H3D⋯O1Wⁱⁱ	0.89	1.99	2.817 (4)	153
Symmetry codes: (i) $[x, -y, z-{\script{1\over 2}}]$ ; (ii) -x, -y, -z+1.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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/S1600536812023550/su2432sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023550/su2432Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023550/su2432Isup3.cml

checkCIF report

Comment top

4-Aminoantipyrene, which contains a pyrazolone ring, is an important compound in the class of analgesic agents used in otic solutions in combination with other analgesics such as benzocaine and phenylephrine (Jain et al., 2003). Pyrazolone is a five-membered lactam ring compound containing two N atoms and a ketone in the same molecule. Such pyrazolone derivatives form a very important class of heterocycles due to their properties and applications (Casas et al., 2007; Zhang et al., 2008). We report herein on the synthesis and crystal structure of the title compound.

The asymmetric unit of title compound, Fig. 1, consists of three components: a 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-aminium cation, a bromide ion and a water molecule. The Br anion is split and appears as two independent half-occupied Br anions, Br1 and Br2, on two-fold rotation axes. In cation, the phenyl ring A (C1–C6) and the 2,3-dihydro-1H-pyrazole ring B (N1/N2/C7/C8/C11) are planar with r.m.s. deviations of 0.019 and 0.014 Å. The dihedral angle between A/B is 62.43 (7)°. The attached atoms O1, N3, C9 and C10 are at a distance of 0.030 (3), 0.053 (3), 0.130 (3) and 0.140 (3) Å respectively, from the mean plane of B. The bond lengths (Allen et al., 1987) and angles are within normal ranges. The crystal structure of some similar compounds have been reported (Chitradevi et al., 2009; Murtaza et al., 2011).

In the crystal, the various components are connected by N—H···O and O—H···Br hydrogen bonds (Table 1 and Fig. 2) to form an infinite one-dimensional arrangement parallel to [001].

Related literature top

For general background on pyrazolone derivatives, see: Casas et al. (2007); Jain et al. (2003); Zhang et al. (2008). For related structures, see: Chitradevi et al. (2009); Murtaza et al.(2011). For bond-length data, see: Allen et al. (1987).

Experimental top

4-Aminoantipyrine (0.203 g, 1.0 mmol) and dibromomethane (0.173 g, 1.0 mmol) were dissolved in water (15 ml). The mixture was refluxed for 3 h and then the solvent was evaporated on rotary evaporator to almost dryness. The crude product was recrystallized from water yielding block-like yellow crystals of the title compound.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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. The molecular structure of the title compound with the atom numbering. The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view along the c axis of the crystal packing of the title compound. H-bonds are shown as dashed lines; see Table 1 for details.

1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-aminium bromide monohydrate top

Crystal data top

C₁₁H₁₄N₃O⁺·Br⁻·H₂O	F(000) = 1232
M_r = 302.17	D_x = 1.572 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2078 reflections
a = 14.9080 (19) Å	θ = 2.7–23.6°
b = 15.3961 (19) Å	µ = 3.21 mm⁻¹
c = 11.1501 (14) Å	T = 296 K
β = 93.657 (2)°	Block, yellow
V = 2554.0 (6) Å³	0.22 × 0.20 × 0.18 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	3222 independent reflections
Radiation source: fine-focus sealed tube	2081 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 28.4°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
T_min = 0.489, T_max = 0.556	k = −20→20
11995 measured reflections	l = −14→14

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0493P)² + 2.161P] where P = (F_o² + 2F_c²)/3
3222 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₁H₁₄N₃O⁺·Br⁻·H₂O	V = 2554.0 (6) Å³
M_r = 302.17	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 14.9080 (19) Å	µ = 3.21 mm⁻¹
b = 15.3961 (19) Å	T = 296 K
c = 11.1501 (14) Å	0.22 × 0.20 × 0.18 mm
β = 93.657 (2)°

Data collection top

Bruker SMART CCD diffractometer	3222 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2081 reflections with I > 2σ(I)
T_min = 0.489, T_max = 0.556	R_int = 0.044
11995 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.04	Δρ_max = 0.48 e Å⁻³
3222 reflections	Δρ_min = −0.40 e Å⁻³
155 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 esds 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	0.11377 (13)	0.01137 (15)	0.64912 (16)	0.0377 (6)
N1	0.24203 (15)	0.09233 (18)	0.61672 (19)	0.0346 (8)
N2	0.28247 (16)	0.12321 (17)	0.5164 (2)	0.0353 (8)
N3	0.08569 (14)	0.01740 (16)	0.38186 (18)	0.0286 (7)
C1	0.2831 (2)	0.0971 (2)	0.7361 (2)	0.0330 (9)
C2	0.2374 (2)	0.1400 (2)	0.8221 (3)	0.0437 (10)
C3	0.2752 (3)	0.1419 (3)	0.9393 (3)	0.0630 (16)
C4	0.3572 (4)	0.1054 (3)	0.9670 (3)	0.080 (2)
C5	0.4009 (3)	0.0627 (4)	0.8813 (4)	0.0781 (18)
C6	0.3637 (2)	0.0573 (3)	0.7639 (3)	0.0551 (13)
C7	0.15821 (17)	0.05670 (17)	0.4544 (2)	0.0256 (8)
C8	0.22945 (18)	0.10325 (18)	0.4178 (2)	0.0275 (8)
C9	0.2493 (2)	0.1347 (2)	0.2962 (3)	0.0391 (10)
C10	0.3605 (2)	0.1798 (2)	0.5249 (3)	0.0466 (10)
C11	0.16456 (18)	0.04939 (18)	0.5808 (2)	0.0281 (8)
Br1	0.00000	0.19903 (3)	0.25000	0.0427 (2)
Br2	0.00000	0.29956 (4)	0.75000	0.0536 (2)
O1W	−0.04198 (19)	0.14894 (18)	0.5343 (2)	0.0651 (10)
H2A	0.18260	0.16700	0.80220	0.0530*
H3A	0.24430	0.16840	0.99940	0.0760*
H3B	0.09260	0.02850	0.30470	0.0430*
H3C	0.03360	0.03920	0.40250	0.0430*
H3D	0.08620	−0.03980	0.39370	0.0430*
H4A	0.38340	0.10970	1.04480	0.0950*
H5A	0.45620	0.03670	0.90140	0.0940*
H6A	0.39310	0.02730	0.70560	0.0660*
H9A	0.30540	0.16560	0.30100	0.0590*
H9B	0.20210	0.17280	0.26610	0.0590*
H9C	0.25330	0.08610	0.24290	0.0590*
H10A	0.37780	0.19340	0.44560	0.0700*
H10B	0.40920	0.15110	0.56910	0.0700*
H10C	0.34590	0.23250	0.56550	0.0700*
H1WA	−0.02990	0.16590	0.46460	0.0780*
H1WB	−0.02990	0.18990	0.58390	0.0780*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0326 (10)	0.0618 (14)	0.0186 (9)	−0.0133 (10)	0.0006 (8)	0.0052 (10)
N1	0.0309 (13)	0.0554 (16)	0.0174 (10)	−0.0125 (12)	0.0004 (9)	0.0000 (11)
N2	0.0365 (14)	0.0473 (15)	0.0222 (11)	−0.0144 (11)	0.0023 (10)	0.0009 (11)
N3	0.0255 (11)	0.0427 (14)	0.0174 (10)	−0.0025 (10)	−0.0004 (8)	−0.0018 (10)
C1	0.0337 (14)	0.0450 (18)	0.0199 (13)	−0.0118 (14)	−0.0022 (11)	0.0009 (13)
C2	0.062 (2)	0.0393 (18)	0.0301 (16)	−0.0069 (16)	0.0059 (15)	−0.0011 (14)
C3	0.106 (4)	0.056 (2)	0.0272 (17)	−0.026 (2)	0.006 (2)	−0.0081 (17)
C4	0.105 (4)	0.098 (4)	0.032 (2)	−0.057 (3)	−0.026 (2)	0.014 (2)
C5	0.047 (2)	0.126 (4)	0.058 (3)	−0.022 (2)	−0.023 (2)	0.028 (3)
C6	0.0382 (18)	0.082 (3)	0.044 (2)	−0.0042 (18)	−0.0058 (15)	0.0046 (18)
C7	0.0251 (13)	0.0337 (14)	0.0180 (12)	−0.0002 (11)	0.0006 (9)	−0.0022 (11)
C8	0.0283 (14)	0.0347 (15)	0.0197 (12)	−0.0011 (12)	0.0032 (10)	0.0006 (11)
C9	0.0439 (18)	0.0505 (19)	0.0232 (13)	−0.0086 (14)	0.0043 (12)	0.0062 (14)
C10	0.0380 (17)	0.065 (2)	0.0369 (17)	−0.0226 (16)	0.0040 (13)	−0.0049 (16)
C11	0.0264 (13)	0.0388 (16)	0.0191 (12)	−0.0037 (12)	0.0011 (10)	0.0002 (12)
Br1	0.0493 (3)	0.0400 (3)	0.0371 (2)	0.0000	−0.0094 (2)	0.0000
Br2	0.0436 (3)	0.0828 (4)	0.0347 (3)	0.0000	0.0055 (2)	0.0000
O1W	0.097 (2)	0.0533 (16)	0.0461 (14)	−0.0197 (15)	0.0132 (14)	0.0000 (13)

Geometric parameters (Å, º) top

O1—C11	1.253 (3)	C4—C5	1.360 (7)
O1W—H1WB	0.8500	C5—C6	1.391 (6)
O1W—H1WA	0.8500	C7—C8	1.365 (4)
N1—C11	1.368 (4)	C7—C11	1.411 (3)
N1—C1	1.431 (3)	C8—C9	1.487 (4)
N1—N2	1.388 (3)	C2—H2A	0.9300
N2—C8	1.348 (3)	C3—H3A	0.9300
N2—C10	1.452 (4)	C4—H4A	0.9300
N3—C7	1.441 (3)	C5—H5A	0.9300
N3—H3C	0.8900	C6—H6A	0.9300
N3—H3D	0.8900	C9—H9B	0.9600
N3—H3B	0.8900	C9—H9C	0.9600
C1—C2	1.380 (4)	C9—H9A	0.9600
C1—C6	1.367 (5)	C10—H10C	0.9600
C2—C3	1.390 (5)	C10—H10A	0.9600
C3—C4	1.363 (7)	C10—H10B	0.9600

H1WA—O1W—H1WB	109.00	N2—C8—C7	107.6 (2)
N2—N1—C1	123.4 (2)	N1—C11—C7	104.8 (2)
N2—N1—C11	109.4 (2)	O1—C11—C7	129.8 (2)
C1—N1—C11	126.9 (2)	O1—C11—N1	125.4 (2)
N1—N2—C8	108.5 (2)	C3—C2—H2A	121.00
N1—N2—C10	122.7 (2)	C1—C2—H2A	121.00
C8—N2—C10	128.0 (2)	C2—C3—H3A	120.00
C7—N3—H3D	109.00	C4—C3—H3A	120.00
C7—N3—H3B	109.00	C5—C4—H4A	120.00
C7—N3—H3C	109.00	C3—C4—H4A	120.00
H3C—N3—H3D	110.00	C4—C5—H5A	120.00
H3B—N3—H3C	110.00	C6—C5—H5A	120.00
H3B—N3—H3D	109.00	C5—C6—H6A	121.00
N1—C1—C6	120.4 (3)	C1—C6—H6A	121.00
N1—C1—C2	118.0 (3)	C8—C9—H9A	109.00
C2—C1—C6	121.5 (3)	C8—C9—H9B	109.00
C1—C2—C3	118.4 (3)	H9A—C9—H9B	109.00
C2—C3—C4	120.6 (3)	H9A—C9—H9C	109.00
C3—C4—C5	120.2 (4)	C8—C9—H9C	110.00
C4—C5—C6	120.7 (4)	H9B—C9—H9C	109.00
C1—C6—C5	118.6 (3)	N2—C10—H10B	110.00
N3—C7—C11	121.8 (2)	N2—C10—H10C	109.00
C8—C7—C11	109.7 (2)	N2—C10—H10A	109.00
N3—C7—C8	128.5 (2)	H10A—C10—H10C	109.00
N2—C8—C9	121.9 (2)	H10B—C10—H10C	109.00
C7—C8—C9	130.3 (2)	H10A—C10—H10B	110.00

C1—N1—N2—C8	175.6 (3)	N1—C1—C2—C3	177.5 (3)
C1—N1—N2—C10	−13.9 (4)	C6—C1—C2—C3	−0.2 (5)
C11—N1—N2—C8	2.5 (3)	N1—C1—C6—C5	−179.3 (4)
C11—N1—N2—C10	173.0 (3)	C2—C1—C6—C5	−1.8 (6)
N2—N1—C1—C2	122.6 (3)	C1—C2—C3—C4	2.8 (6)
C11—N1—C1—C2	−65.5 (4)	C2—C3—C4—C5	−3.4 (7)
N2—N1—C1—C6	−59.8 (4)	C3—C4—C5—C6	1.5 (8)
C11—N1—C1—C6	112.1 (4)	C4—C5—C6—C1	1.1 (7)
N2—N1—C11—C7	−1.1 (3)	N3—C7—C8—C9	6.8 (5)
C1—N1—C11—C7	−174.0 (3)	C11—C7—C8—N2	2.1 (3)
N2—N1—C11—O1	177.5 (3)	C11—C7—C8—C9	−174.3 (3)
C1—N1—C11—O1	4.7 (5)	N3—C7—C11—O1	−0.1 (5)
C10—N2—C8—C9	4.1 (5)	N3—C7—C11—N1	178.5 (2)
C10—N2—C8—C7	−172.6 (3)	C8—C7—C11—O1	−179.2 (3)
N1—N2—C8—C9	174.0 (3)	C8—C7—C11—N1	−0.6 (3)
N1—N2—C8—C7	−2.7 (3)	N3—C7—C8—N2	−176.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···Br1	0.85	2.51	3.360 (2)	173
O1W—H1WB···Br2	0.85	2.52	3.371 (3)	173
N3—H3B···O1ⁱ	0.89	1.89	2.692 (3)	150
N3—H3C···O1W	0.89	2.55	3.321 (3)	146
N3—H3C···O1ⁱⁱ	0.89	2.37	3.004 (3)	129
N3—H3D···O1Wⁱⁱ	0.89	1.99	2.817 (4)	153

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₄N₃O⁺·Br⁻·H₂O
M_r	302.17
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	14.9080 (19), 15.3961 (19), 11.1501 (14)
β (°)	93.657 (2)
V (Å³)	2554.0 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.21
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.489, 0.556
No. of measured, independent and observed [I > 2σ(I)] reflections	11995, 3222, 2081
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.108, 1.04
No. of reflections	3222
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.40

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), 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
O1W—H1WA···Br1	0.85	2.51	3.360 (2)	173
O1W—H1WB···Br2	0.85	2.52	3.371 (3)	173
N3—H3B···O1ⁱ	0.89	1.89	2.692 (3)	150
N3—H3C···O1W	0.89	2.55	3.321 (3)	146
N3—H3C···O1ⁱⁱ	0.89	2.37	3.004 (3)	129
N3—H3D···O1Wⁱⁱ	0.89	1.99	2.817 (4)	153

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

Acknowledgements

The authors thank Liaoning University of Traditional Chinese Medicine for supporting this study (grant No. YXRC0920).

References

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Volume 68| Part 6| June 2012| Page o1964

doi:10.1107/S1600536812023550

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1,5-Di­methyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-aminium bromide monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-aminium bromide monohydrate