5-Acetamido-1H-pyrazole-4-carboxamide monohydrate

El Ghayati, L.; Ramli, Y.; Essassi, E.M.; Taha, M.L.; Mague, J.T.

doi:10.1107/S2414314616009470

organic compounds

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ISSN: 2414-3146

Volume 1| Part 6| June 2016| x160947

doi:10.1107/S2414314616009470

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5-Acetamido-1H-pyrazole-4-carboxamide monohydrate

Lhoussaine El Ghayati,^a Youssef Ramli,^b ^* El Mokhtar Essassi,^c Mohamed Labd Taha ^a and Joel T. Mague ^d

^aLaboratoire de Chemie Bio Organique Appliquée, Faculté des Sciences, Université Ibn Zohr, Agadir, Morocco, ^bLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, University Mohammed V, Rabat, Morocco, ^cLaboratoire de Chimie Organique Hétérocyclique URAC 21, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, and ^dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: yramli76@yahoo.fr

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 8 May 2016; accepted 11 June 2016; online 17 June 2016)

There are two independent molecules of the title carboxamide compound, C₆H₈N₄O₂·H₂O, as well as two independent water molecules in the asymmetric unit. The two independent carboxamide molecules differ primarily in the relative orientations of the peripheral methyl and amino groups. Intramolecular N—H⋯O hydrogen bonds assist in determining the orientations of the acetamido substituents. The three-dimensional crystal packing is directed by a large network of O—H⋯O, N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds.

Keywords: crystal structure; hydrogen bonding; pyrazole; carboxamide.

CCDC reference: 1484691

Structure description

Compounds that contain the pyrazole moiety are known to exhibit a wide range of biological properties (Tantawy et al., 2012 ). As a continuation of our research devoted to the development of carboxamide derivatives of pyrazole (Ramli et al., 2013 ; Karrouchi et al., 2015 ), we prepared the title compound and characterized it by X-ray diffraction. There are two independent molecules of the carboxamide compound as well as two independent water molecules in the asymmetric unit (Fig. 1). The former differ primarily in the orientations of the peripheral methyl and amino groups and their conformations are mainly determined by a pair of intramolecular N—H⋯O hydrogen bonds in each. Intermolecular O—H⋯O, N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds which include those with the lattice water form sheets which are tied to one another by hydrogen bonding with the lattice water (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.90 (2)	2.07 (2)	2.7514 (14)	131.9 (17)
N2—H2A⋯O2	0.90 (2)	2.09 (2)	2.6441 (14)	118.6 (16)
N3—H3A⋯O1	0.883 (19)	2.226 (18)	2.8307 (14)	125.4 (15)
N4—H4A⋯O5	0.897 (19)	2.10 (2)	2.9919 (15)	173.9 (17)
N4—H4B⋯O6ⁱⁱ	0.90 (2)	2.12 (2)	2.9893 (15)	163.2 (17)
C1—H1⋯O6ⁱⁱ	0.95	2.51	3.3791 (16)	153
N6—H6A⋯O3ⁱⁱⁱ	0.89 (2)	2.01 (2)	2.7112 (14)	135.8 (18)
N6—H6A⋯O4	0.89 (2)	2.14 (2)	2.6558 (15)	116.4 (16)
N7—H7A⋯O3	0.887 (18)	2.204 (18)	2.8325 (14)	127.4 (15)
N8—H8A⋯O6	0.914 (19)	2.13 (2)	3.0338 (15)	169.7 (17)
N8—H8B⋯O5^iv	0.907 (18)	2.052 (19)	2.9354 (15)	164.5 (16)
C7—H7⋯O5^iv	0.95	2.63	3.4683 (17)	147
C11—H11B⋯N5^v	0.98	2.44	3.3337 (17)	152
O5—H5D⋯O2^vi	0.93 (2)	1.87 (2)	2.7658 (14)	161.1 (19)
O5—H5E⋯O1^vii	0.87 (2)	1.97 (2)	2.8269 (15)	168 (2)
O6—H6B⋯N1^vi	0.85 (2)	2.13 (2)	2.9448 (16)	162.5 (18)
O6—H6C⋯O4^v	0.93 (2)	1.83 (2)	2.7406 (14)	165.0 (18)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vii) -x+1, -y, -z.

Figure 1
The asymmetric unit of the title compound, showing the atom-labelling scheme and 50% probability displacement ellipsoids.

Figure 2
Packing viewed along the b axis with O—H⋯O and N—H⋯O hydrogen bonds when shown, indicated as red and blue dotted lines, respectively.

Synthesis and crystallization

5-Amino-1H-pyrazole-4-carboxamide (0.669 g, 3.69 mmol) was stirred in refluxing glacial acetic acid for 1 h. The mixture was cooled to room temperature and the resulting solid was filtered off and dried to obtain the acetylated product (yield; 80%; m.p. = 387–389 K). Crystals suitable for X-ray analysis were obtained by recrystallization from wet ethanol.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₆H₈N₄O₂·H₂O
M_r	186.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	9.7953 (3), 12.4179 (3), 14.4833 (4)
β (°)	107.490 (1)
V (Å³)	1680.26 (8)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	1.02
Crystal size (mm)	0.18 × 0.11 × 0.11

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.81, 0.90
No. of measured, independent and observed [I > 2σ(I)] reflections	13029, 3358, 2970
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.096, 1.07
No. of reflections	3358
No. of parameters	285
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.32
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1484691

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616009470/tk4015sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616009470/tk4015Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616009470/tk4015Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

5-Acetamido-1H-pyrazole-4-carboxamide monohydrate top

Crystal data top

C₆H₈N₄O₂·H₂O	F(000) = 784
M_r = 186.18	D_x = 1.472 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 9.7953 (3) Å	Cell parameters from 9957 reflections
b = 12.4179 (3) Å	θ = 3.2–74.5°
c = 14.4833 (4) Å	µ = 1.02 mm⁻¹
β = 107.490 (1)°	T = 150 K
V = 1680.26 (8) Å³	Block, colourless
Z = 8	0.18 × 0.11 × 0.11 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3358 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2970 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.030
Detector resolution: 10.4167 pixels mm^-1	θ_max = 74.5°, θ_min = 4.8°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −14→15
T_min = 0.81, T_max = 0.90	l = −16→18
13029 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)] = 0.036	Hydrogen site location: mixed
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.055P)² + 0.420P] where P = (F_o² + 2F_c²)/3
3358 reflections	(Δ/σ)_max < 0.001
285 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Special details top

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.64084 (10)	0.12975 (7)	0.15757 (7)	0.0275 (2)
O2	1.01723 (10)	0.38984 (7)	0.35365 (7)	0.0275 (2)
N1	0.64268 (12)	0.49783 (9)	0.18328 (9)	0.0243 (2)
N2	0.76322 (12)	0.44563 (9)	0.23727 (8)	0.0216 (2)
H2A	0.839 (2)	0.4803 (16)	0.2766 (16)	0.047 (5)*
N3	0.85744 (12)	0.26580 (9)	0.27281 (8)	0.0216 (2)
H3A	0.8390 (19)	0.1967 (15)	0.2611 (13)	0.036 (5)*
N4	0.43236 (12)	0.20207 (9)	0.06553 (9)	0.0253 (3)
H4A	0.3977 (19)	0.1368 (16)	0.0443 (13)	0.038 (5)*
H4B	0.379 (2)	0.2609 (16)	0.0446 (14)	0.039 (5)*
C1	0.55571 (13)	0.42000 (10)	0.13782 (10)	0.0220 (3)
H1	0.4627	0.4320	0.0945	0.026*
C2	0.61742 (13)	0.31744 (10)	0.16125 (9)	0.0194 (3)
C3	0.75180 (13)	0.33861 (10)	0.22646 (9)	0.0190 (3)
C4	0.98718 (13)	0.29469 (10)	0.33478 (9)	0.0216 (3)
C5	1.08922 (14)	0.20491 (11)	0.37679 (11)	0.0281 (3)
H5A	1.0576	0.1391	0.3390	0.042*
H5B	1.0916	0.1926	0.4441	0.042*
H5C	1.1852	0.2243	0.3747	0.042*
C6	0.56270 (13)	0.20997 (10)	0.12835 (9)	0.0201 (3)
O3	0.40206 (10)	0.25721 (7)	0.29665 (7)	0.0273 (2)
O4	0.00312 (10)	0.51118 (7)	0.11825 (7)	0.0280 (2)
N5	0.33747 (12)	0.61884 (9)	0.33187 (9)	0.0256 (3)
N6	0.23058 (12)	0.56693 (9)	0.26354 (8)	0.0229 (2)
H6A	0.154 (2)	0.6021 (16)	0.2283 (15)	0.048 (5)*
N7	0.17347 (11)	0.39040 (9)	0.19132 (8)	0.0206 (2)
H7A	0.2026 (19)	0.3224 (15)	0.1970 (13)	0.035 (5)*
N8	0.59719 (12)	0.33310 (9)	0.40152 (9)	0.0237 (2)
H8A	0.642 (2)	0.2676 (16)	0.4097 (13)	0.040 (5)*
H8B	0.6437 (19)	0.3930 (15)	0.4305 (13)	0.032 (4)*
C7	0.43460 (14)	0.54373 (10)	0.36760 (10)	0.0229 (3)
H7	0.5221	0.5564	0.4170	0.028*
C8	0.39327 (13)	0.44268 (10)	0.32381 (9)	0.0196 (3)
C9	0.26034 (13)	0.46235 (10)	0.25628 (9)	0.0193 (3)
C10	0.04738 (13)	0.41788 (10)	0.12501 (9)	0.0212 (3)
C11	−0.03388 (14)	0.32910 (11)	0.06167 (10)	0.0258 (3)
H11A	−0.1205	0.3127	0.0796	0.039*
H11B	0.0264	0.2647	0.0703	0.039*
H11C	−0.0607	0.3520	−0.0062	0.039*
C12	0.46470 (13)	0.33801 (10)	0.33990 (9)	0.0197 (3)
O5	0.29513 (11)	−0.00815 (8)	−0.01083 (8)	0.0294 (2)
H5D	0.340 (2)	−0.0463 (17)	0.0455 (17)	0.051 (6)*
H5E	0.322 (2)	−0.0375 (18)	−0.0572 (17)	0.057 (6)*
O6	0.75030 (11)	0.11930 (8)	0.45538 (8)	0.0289 (2)
H6B	0.790 (2)	0.0974 (16)	0.4142 (15)	0.042 (5)*
H6C	0.667 (2)	0.0781 (16)	0.4413 (14)	0.047 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0272 (5)	0.0164 (4)	0.0306 (5)	0.0028 (4)	−0.0038 (4)	−0.0002 (4)
O2	0.0243 (5)	0.0243 (5)	0.0283 (5)	−0.0054 (4)	−0.0005 (4)	−0.0008 (4)
N1	0.0216 (5)	0.0179 (5)	0.0291 (6)	0.0007 (4)	0.0010 (5)	0.0015 (4)
N2	0.0195 (5)	0.0167 (5)	0.0249 (6)	−0.0016 (4)	0.0008 (5)	0.0001 (4)
N3	0.0197 (5)	0.0179 (5)	0.0231 (5)	−0.0001 (4)	0.0003 (4)	0.0001 (4)
N4	0.0222 (6)	0.0166 (5)	0.0304 (6)	−0.0009 (4)	−0.0024 (5)	−0.0015 (5)
C1	0.0199 (6)	0.0180 (6)	0.0251 (6)	0.0003 (5)	0.0022 (5)	0.0007 (5)
C2	0.0183 (6)	0.0178 (6)	0.0203 (6)	−0.0004 (4)	0.0029 (5)	0.0004 (5)
C3	0.0203 (6)	0.0171 (6)	0.0186 (6)	−0.0009 (4)	0.0043 (5)	0.0001 (5)
C4	0.0184 (6)	0.0256 (6)	0.0193 (6)	−0.0018 (5)	0.0034 (5)	0.0009 (5)
C5	0.0210 (6)	0.0288 (7)	0.0297 (7)	0.0022 (5)	0.0004 (5)	0.0023 (6)
C6	0.0216 (6)	0.0169 (6)	0.0192 (6)	0.0001 (5)	0.0022 (5)	−0.0001 (5)
O3	0.0228 (5)	0.0164 (4)	0.0361 (5)	−0.0024 (3)	−0.0012 (4)	−0.0038 (4)
O4	0.0237 (5)	0.0220 (5)	0.0320 (5)	0.0042 (4)	−0.0012 (4)	0.0015 (4)
N5	0.0239 (5)	0.0179 (5)	0.0292 (6)	−0.0014 (4)	−0.0009 (5)	−0.0032 (4)
N6	0.0207 (5)	0.0161 (5)	0.0269 (6)	0.0015 (4)	−0.0004 (5)	−0.0005 (4)
N7	0.0189 (5)	0.0165 (5)	0.0231 (5)	0.0006 (4)	0.0011 (4)	−0.0002 (4)
N8	0.0200 (5)	0.0172 (5)	0.0289 (6)	0.0007 (4)	−0.0003 (5)	−0.0009 (5)
C7	0.0209 (6)	0.0188 (6)	0.0252 (6)	−0.0012 (5)	0.0011 (5)	−0.0010 (5)
C8	0.0181 (6)	0.0166 (6)	0.0218 (6)	−0.0003 (4)	0.0026 (5)	0.0004 (5)
C9	0.0188 (6)	0.0164 (6)	0.0215 (6)	−0.0004 (4)	0.0041 (5)	0.0006 (5)
C10	0.0184 (6)	0.0219 (6)	0.0216 (6)	0.0000 (5)	0.0034 (5)	0.0025 (5)
C11	0.0241 (6)	0.0232 (6)	0.0256 (7)	−0.0025 (5)	0.0006 (5)	0.0015 (5)
C12	0.0191 (6)	0.0169 (6)	0.0216 (6)	−0.0013 (4)	0.0037 (5)	0.0008 (5)
O5	0.0303 (5)	0.0244 (5)	0.0280 (5)	0.0074 (4)	0.0005 (4)	0.0002 (4)
O6	0.0222 (5)	0.0249 (5)	0.0358 (6)	−0.0022 (4)	0.0030 (4)	−0.0093 (4)

Geometric parameters (Å, º) top

O1—C6	1.2500 (15)	N5—C7	1.3218 (17)
O2—C4	1.2284 (16)	N5—N6	1.3668 (15)
N1—C1	1.3252 (17)	N6—C9	1.3420 (16)
N1—N2	1.3677 (15)	N6—H6A	0.89 (2)
N2—C3	1.3389 (16)	N7—C10	1.3606 (17)
N2—H2A	0.90 (2)	N7—C9	1.3878 (16)
N3—C4	1.3652 (17)	N7—H7A	0.887 (18)
N3—C3	1.3863 (16)	N8—C12	1.3373 (17)
N3—H3A	0.883 (19)	N8—H8A	0.914 (19)
N4—C6	1.3301 (17)	N8—H8B	0.907 (18)
N4—H4A	0.897 (19)	C7—C8	1.4094 (17)
N4—H4B	0.90 (2)	C7—H7	0.9500
C1—C2	1.4069 (17)	C8—C9	1.3950 (18)
C1—H1	0.9500	C8—C12	1.4612 (17)
C2—C3	1.3952 (17)	C10—C11	1.5005 (18)
C2—C6	1.4635 (17)	C11—H11A	0.9800
C4—C5	1.4989 (18)	C11—H11B	0.9800
C5—H5A	0.9800	C11—H11C	0.9800
C5—H5B	0.9800	O5—H5D	0.93 (2)
C5—H5C	0.9800	O5—H5E	0.87 (2)
O3—C12	1.2429 (15)	O6—H6B	0.85 (2)
O4—C10	1.2307 (16)	O6—H6C	0.93 (2)

C1—N1—N2	104.71 (10)	C9—N6—N5	112.09 (11)
C3—N2—N1	112.09 (11)	C9—N6—H6A	126.8 (13)
C3—N2—H2A	125.0 (13)	N5—N6—H6A	121.1 (13)
N1—N2—H2A	122.8 (13)	C10—N7—C9	123.96 (11)
C4—N3—C3	123.98 (11)	C10—N7—H7A	120.2 (12)
C4—N3—H3A	118.6 (12)	C9—N7—H7A	115.8 (12)
C3—N3—H3A	117.4 (12)	C12—N8—H8A	117.2 (12)
C6—N4—H4A	119.2 (12)	C12—N8—H8B	121.5 (11)
C6—N4—H4B	121.0 (12)	H8A—N8—H8B	121.1 (16)
H4A—N4—H4B	119.8 (16)	N5—C7—C8	112.11 (11)
N1—C1—C2	112.02 (11)	N5—C7—H7	123.9
N1—C1—H1	124.0	C8—C7—H7	123.9
C2—C1—H1	124.0	C9—C8—C7	103.94 (11)
C3—C2—C1	104.02 (11)	C9—C8—C12	124.67 (11)
C3—C2—C6	124.82 (11)	C7—C8—C12	131.39 (12)
C1—C2—C6	131.16 (12)	N6—C9—N7	124.94 (11)
N2—C3—N3	124.53 (11)	N6—C9—C8	107.06 (11)
N2—C3—C2	107.15 (11)	N7—C9—C8	127.99 (11)
N3—C3—C2	128.32 (11)	O4—C10—N7	121.03 (12)
O2—C4—N3	120.83 (12)	O4—C10—C11	122.25 (12)
O2—C4—C5	122.63 (12)	N7—C10—C11	116.72 (11)
N3—C4—C5	116.54 (11)	C10—C11—H11A	109.5
C4—C5—H5A	109.5	C10—C11—H11B	109.5
C4—C5—H5B	109.5	H11A—C11—H11B	109.5
H5A—C5—H5B	109.5	C10—C11—H11C	109.5
C4—C5—H5C	109.5	H11A—C11—H11C	109.5
H5A—C5—H5C	109.5	H11B—C11—H11C	109.5
H5B—C5—H5C	109.5	O3—C12—N8	122.18 (12)
O1—C6—N4	122.48 (12)	O3—C12—C8	119.84 (11)
O1—C6—C2	119.30 (11)	N8—C12—C8	117.98 (11)
N4—C6—C2	118.18 (11)	H5D—O5—H5E	106.9 (19)
C7—N5—N6	104.79 (10)	H6B—O6—H6C	102.9 (17)

C1—N1—N2—C3	−0.37 (14)	C7—N5—N6—C9	−0.37 (15)
N2—N1—C1—C2	0.03 (15)	N6—N5—C7—C8	−0.04 (15)
N1—C1—C2—C3	0.29 (15)	N5—C7—C8—C9	0.41 (15)
N1—C1—C2—C6	−179.28 (13)	N5—C7—C8—C12	−179.72 (13)
N1—N2—C3—N3	−179.73 (11)	N5—N6—C9—N7	−178.19 (12)
N1—N2—C3—C2	0.56 (15)	N5—N6—C9—C8	0.63 (15)
C4—N3—C3—N2	−0.6 (2)	C10—N7—C9—N6	1.4 (2)
C4—N3—C3—C2	179.02 (12)	C10—N7—C9—C8	−177.21 (13)
C1—C2—C3—N2	−0.50 (14)	C7—C8—C9—N6	−0.60 (14)
C6—C2—C3—N2	179.11 (12)	C12—C8—C9—N6	179.51 (12)
C1—C2—C3—N3	179.81 (12)	C7—C8—C9—N7	178.17 (12)
C6—C2—C3—N3	−0.6 (2)	C12—C8—C9—N7	−1.7 (2)
C3—N3—C4—O2	0.5 (2)	C9—N7—C10—O4	0.81 (19)
C3—N3—C4—C5	−178.89 (12)	C9—N7—C10—C11	−178.96 (12)
C3—C2—C6—O1	−1.9 (2)	C9—C8—C12—O3	−5.3 (2)
C1—C2—C6—O1	177.57 (13)	C7—C8—C12—O3	174.86 (13)
C3—C2—C6—N4	−179.75 (12)	C9—C8—C12—N8	174.62 (12)
C1—C2—C6—N4	−0.3 (2)	C7—C8—C12—N8	−5.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.90 (2)	2.07 (2)	2.7514 (14)	131.9 (17)
N2—H2A···O2	0.90 (2)	2.09 (2)	2.6441 (14)	118.6 (16)
N3—H3A···O1	0.883 (19)	2.226 (18)	2.8307 (14)	125.4 (15)
N4—H4A···O5	0.897 (19)	2.10 (2)	2.9919 (15)	173.9 (17)
N4—H4B···O6ⁱⁱ	0.90 (2)	2.12 (2)	2.9893 (15)	163.2 (17)
C1—H1···O6ⁱⁱ	0.95	2.51	3.3791 (16)	153
N6—H6A···O3ⁱⁱⁱ	0.89 (2)	2.01 (2)	2.7112 (14)	135.8 (18)
N6—H6A···O4	0.89 (2)	2.14 (2)	2.6558 (15)	116.4 (16)
N7—H7A···O3	0.887 (18)	2.204 (18)	2.8325 (14)	127.4 (15)
N8—H8A···O6	0.914 (19)	2.13 (2)	3.0338 (15)	169.7 (17)
N8—H8B···O5^iv	0.907 (18)	2.052 (19)	2.9354 (15)	164.5 (16)
C7—H7···O5^iv	0.95	2.63	3.4683 (17)	147
C11—H11B···N5^v	0.98	2.44	3.3337 (17)	152
O5—H5D···O2^vi	0.93 (2)	1.87 (2)	2.7658 (14)	161.1 (19)
O5—H5E···O1^vii	0.87 (2)	1.97 (2)	2.8269 (15)	168 (2)
O6—H6B···N1^vi	0.85 (2)	2.13 (2)	2.9448 (16)	162.5 (18)
O6—H6C···O4^v	0.93 (2)	1.83 (2)	2.7406 (14)	165.0 (18)

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1/2, y+1/2, −z+1/2; (iv) x+1/2, −y+1/2, z+1/2; (v) −x+1/2, y−1/2, −z+1/2; (vi) −x+3/2, y−1/2, −z+1/2; (vii) −x+1, −y, −z.

Acknowledgements

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Karrouchi, K., Ansar, M., Radi, S., Saadi, M. & El Ammari, L. (2015). Acta Cryst. E71, o890–o891. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ramli, Y., Karrouchi, K., Essassi, E. M. & El Ammari, L. (2013). Acta Cryst. E69, o1320–o1321. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Tantawy, A. S., Nasr, M. N. A., El-Sayed, M. M. A. & Tawfik, S. S. (2012). Med. Chem. Res. 21, 4139–4149. CrossRef CAS Google Scholar

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Volume 1| Part 6| June 2016| x160947

doi:10.1107/S2414314616009470

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

5-Acetamido-1H-pyrazole-4-carboxamide monohydrate

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds