organic compounds
5-Acetamido-1H-pyrazole-4-carboxamide monohydrate
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
There are two independent molecules of the title carboxamide compound, C6H8N4O2·H2O, as well as two independent water molecules in the 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 (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).
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 .
details are summarized in Table 2
|
Structural data
CCDC reference: 1484691
10.1107/S2414314616009470/tk4015sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616009470/tk4015Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616009470/tk4015Isup3.cml
Data collection: APEX3 (Bruker, 2016); cell
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).C6H8N4O2·H2O | F(000) = 784 |
Mr = 186.18 | Dx = 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 |
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 | Rint = 0.030 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 74.5°, θmin = 4.8° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −14→15 |
Tmin = 0.81, Tmax = 0.90 | l = −16→18 |
13029 measured reflections |
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(Fo2) + (0.055P)2 + 0.420P] where P = (Fo2 + 2Fc2)/3 |
3358 reflections | (Δ/σ)max < 0.001 |
285 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
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)* |
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) |
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) |
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···O5iv | 0.907 (18) | 2.052 (19) | 2.9354 (15) | 164.5 (16) |
C7—H7···O5iv | 0.95 | 2.63 | 3.4683 (17) | 147 |
C11—H11B···N5v | 0.98 | 2.44 | 3.3337 (17) | 152 |
O5—H5D···O2vi | 0.93 (2) | 1.87 (2) | 2.7658 (14) | 161.1 (19) |
O5—H5E···O1vii | 0.87 (2) | 1.97 (2) | 2.8269 (15) | 168 (2) |
O6—H6B···N1vi | 0.85 (2) | 2.13 (2) | 2.9448 (16) | 162.5 (18) |
O6—H6C···O4v | 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
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