N-{2-[2-(5-Methyl-1H-pyrazol-3-yl)acetamido]­phen­yl}benzamide monohydrate

Chkirate, K.; Mague, J.T.; Sebbar, N.K.; Ouzidan, Y.; Essassi, E.M.

doi:10.1107/S2414314617002516

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170251

https://doi.org/10.1107/S2414314617002516

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N-{2-[2-(5-Methyl-1H-pyrazol-3-yl)acetamido]phenyl}benzamide monohydrate

Karim Chkirate,^a ^* Joel T. Mague,^b Nada Kheira Sebbar,^a Younes Ouzidan ^c and El Mokhtar Essassi ^a

^aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, and ^cLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Imouzzer, BP 2202, Fez, Morocco
^*Correspondence e-mail: chkiratekarim@gmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 12 February 2017; accepted 13 February 2017; online 24 February 2017)

The asymmetric unit of the title compound, C₁₉H₁₈N₄O₂·H₂O, comprises the U-shaped pyrazole derivative and a solvent water molecule. The molecular conformation is partly determined by an intramolecular N—H⋯O hydrogen bond. The crystal packing is directed by an extensive network of O—H⋯O, N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds together with C—H⋯π(ring) contacts that generate a three-dimensional network.

Keywords: crystal structure; hydrogen bond; pyrazole.

CCDC reference: 1532509

Structure description

Pyrazole derivatives have pharmacologically attractive biological applications (Havrylyuk et al., 2016 ) and interesting therapeutic properties (Khan et al., 2016 ). These compounds have been synthesized as target structures by many researchers and have been evaluated for their beneficial bioactivity and for the rational design of a new generation of small molecule drugs (Küçükgüzel & Şenkardeş, 2015 ). Continuing our research in this field (Chkirate et al., 2001 ), we have synthesized N-2-benzamido-phenyl-5-methyl-pyrazol-3-yl acetamide by reacting benzoyl chloride with N-2-aminophenyl-5-methyl-pyrazol-3-yl acetamide. The latter was obtained by the action of hydrazine on the 4-(oxopropylidene)-1,5-benzodiazepin-2-one (El Abbassi et al., 1989 ).

The title molecule adopts a U-shaped conformation due, in part, to the intramolecular N1—H1⋯O2 hydrogen bond (Table 1 and Fig. 1). The dihedral angle between the C1–C6 and C8–C13 benzene rings is 49.67 (5)° while that between the latter ring and the pyrazole ring is 64.49 (6)°. The packing is governed largely by a network of intermolecular hydrogen bonds including N2—H2A⋯N3ⁱ, N4—H4A⋯O3ⁱⁱ, O3—H3A⋯O1, O3—H3B⋯O2^iv and C12—H12⋯O3ⁱⁱⁱ (Table 1 and Fig. 2). In addition there are two C—H⋯π(ring) interactions: C15—H15A⋯π(C8–C13)^v and C19—H19A⋯π(N3,N4,C16–C18)^vi, Table 1, that also contribute to the crystal packing. These contacts combine to generate a three-dimensional network, Fig. 2.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg3 are the centroids of the N3,N4,C16–C18 and C8–C13 rings respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.88 (2)	2.09 (2)	2.7902 (17)	135.0 (19)
N2—H2A⋯N3ⁱ	0.95 (2)	1.98 (2)	2.9209 (17)	176.4 (17)
N4—H4A⋯O3ⁱⁱ	0.92 (2)	1.88 (2)	2.7883 (16)	166.9 (19)
C12—H12⋯O3ⁱⁱⁱ	0.978 (19)	2.464 (19)	3.4042 (19)	161.2 (14)
O3—H3A⋯O1	0.87 (3)	1.89 (3)	2.7445 (16)	167 (2)
O3—H3B⋯O2^iv	0.94 (3)	1.83 (3)	2.7575 (15)	169 (2)
C15—H15A⋯Cg3^v	0.957 (19)	2.893 (18)	3.8485 (15)	174.0 (14)
C19—H19A⋯Cg1^vi	0.98 (3)	2.86 (3)	3.645 (2)	138 (2)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+1, -z+1; (iii) x, y, z+1; (iv) -x+2, -y+1, -z+1; (v) -x+2, -y+1, -z+2; (vi) -x+1, -y+2, -z+2.

Figure 1
The asymmetric unit of the title compound, showing the atom-labelling scheme and 50% probability displacement ellipsoids. The intramolecular N—H⋯O hydrogen bond is shown as a blue dashed line.

Figure 2
Crystal packing projected onto (111) with hydrogen bonds shown as dashed lines [O—H⋯O (red); N—H⋯O (blue); N—H⋯N (green); C—H⋯O (black)].

Synthesis and crystallization

To a solution of 5 × 10⁻⁴ mol of N-(2-aminophenyl-5-methyl-pyrazol-3-yl)acetamide dissolved in 10 ml of ethanol was added 5 × 10⁻⁴ mol of benzoyl chloride. The mixture was stirred for 24 h at room temperature. After filtration and recrystallization from ethanol, colourless single crystals were obtained with a yield of 66%.

Refinement

Crystal and refinement details appear in Table 2. Eleven reflections appearing near the top of the frames on which they were recorded were omitted from the fineal refinement as they appeared to have been partially obscured by the nozzle of the low-temperature attachment.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₁₈N₄O₂·H₂O
M_r	352.39
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	150
a, b, c (Å)	8.4220 (3), 10.0410 (4), 10.8799 (4)
α, β, γ (°)	101.889 (2), 94.104 (2), 90.402 (1)
V (Å³)	897.79 (6)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	0.74
Crystal size (mm)	0.15 × 0.14 × 0.10

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.85, 0.93
No. of measured, independent and observed [I > 2σ(I)] reflections	6831, 3279, 2846
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.114, 1.06
No. of reflections	3279
No. of parameters	316
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21
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: 1532509

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617002516/sj4090sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002516/sj4090Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617002516/sj4090Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314617002516/sj4090Isup4.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).

N-{2-[2-(5-Methyl-1H-pyrazol-3-yl)acetamido]phenyl}benzamide monohydrate top

Crystal data top

C₁₉H₁₈N₄O₂·H₂O	Z = 2
M_r = 352.39	F(000) = 372
Triclinic, P1	D_x = 1.304 Mg m⁻³
a = 8.4220 (3) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.0410 (4) Å	Cell parameters from 5496 reflections
c = 10.8799 (4) Å	θ = 4.5–71.9°
α = 101.889 (2)°	µ = 0.74 mm⁻¹
β = 94.104 (2)°	T = 150 K
γ = 90.402 (1)°	Block, colourless
V = 897.79 (6) Å³	0.15 × 0.14 × 0.10 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3279 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2846 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.2°, θ_min = 4.2°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −11→12
T_min = 0.85, T_max = 0.93	l = −12→13
6831 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	All H-atom parameters refined
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0641P)² + 0.2007P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3279 reflections	Δρ_max = 0.20 e Å⁻³
316 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0164 (16)

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.

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

	x	y	z	U_iso*/U_eq
O1	0.79721 (16)	0.27601 (13)	0.44040 (10)	0.0459 (3)
O2	0.93031 (11)	0.56110 (10)	0.87382 (10)	0.0299 (3)
N1	0.83593 (16)	0.38781 (15)	0.64465 (12)	0.0344 (3)
H1	0.828 (3)	0.468 (2)	0.695 (2)	0.053 (6)*
N2	0.77023 (13)	0.38862 (11)	0.89936 (10)	0.0226 (3)
H2A	0.693 (2)	0.3631 (18)	0.9497 (18)	0.037 (5)*
N3	0.47391 (14)	0.69851 (11)	0.95462 (11)	0.0266 (3)
N4	0.42223 (14)	0.79751 (12)	0.89372 (11)	0.0275 (3)
H4A	0.315 (3)	0.798 (2)	0.870 (2)	0.050 (6)*
C1	0.73450 (18)	0.51188 (18)	0.48918 (14)	0.0354 (4)
C2	0.7643 (2)	0.63951 (19)	0.56712 (16)	0.0421 (4)
H2	0.830 (2)	0.651 (2)	0.648 (2)	0.050 (5)*
C3	0.7021 (2)	0.7553 (2)	0.53373 (19)	0.0514 (5)
H3	0.725 (3)	0.844 (3)	0.588 (2)	0.067 (7)*
C4	0.6082 (2)	0.7447 (2)	0.42178 (19)	0.0541 (5)
H4	0.569 (3)	0.827 (2)	0.402 (2)	0.062 (6)*
C5	0.5786 (2)	0.6188 (2)	0.34362 (17)	0.0499 (5)
H5	0.509 (3)	0.608 (2)	0.264 (2)	0.055 (6)*
C6	0.6409 (2)	0.5025 (2)	0.37623 (15)	0.0433 (4)
H6	0.619 (3)	0.408 (2)	0.321 (2)	0.055 (6)*
C7	0.79287 (18)	0.38224 (17)	0.52099 (14)	0.0352 (4)
C8	0.88775 (17)	0.27928 (15)	0.70092 (13)	0.0308 (3)
C9	0.9735 (2)	0.17147 (18)	0.63698 (16)	0.0416 (4)
H9	0.996 (3)	0.177 (2)	0.552 (2)	0.057 (6)*
C10	1.0224 (2)	0.06677 (18)	0.69444 (16)	0.0411 (4)
H10	1.082 (2)	−0.006 (2)	0.646 (2)	0.051 (6)*
C11	0.98655 (19)	0.06710 (15)	0.81653 (15)	0.0348 (3)
H11	1.020 (2)	−0.006 (2)	0.858 (2)	0.050 (6)*
C12	0.90333 (17)	0.17445 (14)	0.88159 (14)	0.0280 (3)
H12	0.880 (2)	0.1783 (17)	0.9689 (18)	0.033 (4)*
C13	0.85463 (15)	0.28126 (13)	0.82543 (13)	0.0247 (3)
C14	0.82037 (15)	0.51951 (13)	0.92651 (12)	0.0230 (3)
C15	0.73064 (17)	0.61472 (13)	1.02316 (13)	0.0254 (3)
H15A	0.810 (2)	0.6650 (18)	1.0828 (18)	0.035 (4)*
H15B	0.664 (2)	0.5616 (18)	1.0653 (17)	0.032 (4)*
C16	0.63237 (16)	0.71090 (13)	0.96200 (13)	0.0251 (3)
C17	0.68045 (17)	0.81614 (14)	0.90528 (15)	0.0305 (3)
H17	0.793 (2)	0.8410 (19)	0.8959 (18)	0.039 (5)*
C18	0.54213 (17)	0.86907 (14)	0.86181 (14)	0.0279 (3)
C19	0.5098 (2)	0.98073 (17)	0.79240 (18)	0.0390 (4)
H19A	0.445 (3)	1.052 (3)	0.838 (3)	0.079 (8)*
H19B	0.609 (3)	1.019 (2)	0.772 (2)	0.064 (7)*
H19C	0.445 (3)	0.947 (2)	0.714 (2)	0.052 (6)*
O3	0.89511 (12)	0.24005 (10)	0.20075 (10)	0.0295 (3)
H3A	0.872 (3)	0.263 (3)	0.278 (3)	0.074 (8)*
H3B	0.946 (3)	0.315 (3)	0.181 (2)	0.061 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0582 (7)	0.0541 (7)	0.0246 (6)	0.0020 (6)	0.0032 (5)	0.0061 (5)
O2	0.0293 (5)	0.0313 (5)	0.0310 (5)	−0.0026 (4)	0.0063 (4)	0.0097 (4)
N1	0.0403 (7)	0.0429 (7)	0.0214 (6)	0.0066 (6)	0.0041 (5)	0.0091 (5)
N2	0.0248 (5)	0.0240 (5)	0.0202 (5)	0.0007 (4)	0.0042 (4)	0.0061 (4)
N3	0.0275 (6)	0.0259 (6)	0.0275 (6)	0.0019 (4)	0.0033 (5)	0.0074 (4)
N4	0.0265 (6)	0.0270 (6)	0.0303 (6)	0.0021 (5)	0.0022 (5)	0.0090 (5)
C1	0.0303 (7)	0.0556 (10)	0.0240 (7)	−0.0008 (7)	0.0050 (6)	0.0156 (6)
C2	0.0413 (9)	0.0539 (10)	0.0349 (9)	−0.0047 (7)	−0.0044 (7)	0.0203 (7)
C3	0.0563 (11)	0.0548 (11)	0.0477 (11)	−0.0014 (9)	0.0004 (9)	0.0228 (9)
C4	0.0508 (11)	0.0746 (14)	0.0483 (11)	0.0143 (10)	0.0088 (9)	0.0368 (10)
C5	0.0385 (9)	0.0839 (14)	0.0327 (9)	0.0126 (9)	0.0027 (7)	0.0245 (9)
C6	0.0357 (8)	0.0713 (12)	0.0251 (8)	0.0046 (8)	0.0028 (6)	0.0151 (7)
C7	0.0323 (7)	0.0530 (9)	0.0217 (7)	−0.0005 (7)	0.0055 (6)	0.0099 (6)
C8	0.0311 (7)	0.0371 (8)	0.0245 (7)	0.0046 (6)	0.0032 (6)	0.0069 (6)
C9	0.0448 (9)	0.0514 (10)	0.0279 (8)	0.0117 (8)	0.0096 (7)	0.0041 (7)
C10	0.0412 (8)	0.0415 (9)	0.0370 (9)	0.0115 (7)	0.0082 (7)	−0.0023 (7)
C11	0.0359 (8)	0.0288 (7)	0.0389 (8)	0.0034 (6)	0.0042 (7)	0.0047 (6)
C12	0.0297 (7)	0.0266 (7)	0.0279 (7)	−0.0002 (5)	0.0041 (6)	0.0055 (5)
C13	0.0237 (6)	0.0267 (6)	0.0226 (7)	0.0000 (5)	0.0023 (5)	0.0026 (5)
C14	0.0241 (6)	0.0264 (6)	0.0200 (6)	0.0016 (5)	−0.0007 (5)	0.0089 (5)
C15	0.0297 (7)	0.0237 (6)	0.0234 (7)	0.0021 (5)	0.0023 (6)	0.0063 (5)
C16	0.0276 (6)	0.0218 (6)	0.0253 (7)	0.0007 (5)	0.0016 (5)	0.0036 (5)
C17	0.0275 (7)	0.0279 (7)	0.0386 (8)	−0.0009 (6)	0.0015 (6)	0.0128 (6)
C18	0.0307 (7)	0.0240 (6)	0.0297 (7)	−0.0011 (5)	0.0024 (6)	0.0071 (5)
C19	0.0421 (9)	0.0328 (8)	0.0464 (10)	0.0036 (7)	−0.0005 (8)	0.0191 (7)
O3	0.0316 (5)	0.0291 (5)	0.0289 (6)	−0.0006 (4)	0.0034 (4)	0.0082 (4)

Geometric parameters (Å, º) top

O1—C7	1.236 (2)	C8—C9	1.397 (2)
O2—C14	1.2368 (16)	C8—C13	1.399 (2)
N1—C7	1.3578 (19)	C9—C10	1.380 (3)
N1—C8	1.413 (2)	C9—H9	0.97 (2)
N1—H1	0.88 (2)	C10—C11	1.382 (2)
N2—C14	1.3444 (17)	C10—H10	0.97 (2)
N2—C13	1.4316 (17)	C11—C12	1.386 (2)
N2—H2A	0.95 (2)	C11—H11	0.98 (2)
N3—C16	1.3346 (18)	C12—C13	1.390 (2)
N3—N4	1.3611 (16)	C12—H12	0.978 (19)
N4—C18	1.3414 (19)	C14—C15	1.5167 (18)
N4—H4A	0.92 (2)	C15—C16	1.5026 (19)
C1—C2	1.393 (3)	C15—H15A	0.957 (19)
C1—C6	1.398 (2)	C15—H15B	0.972 (19)
C1—C7	1.492 (2)	C16—C17	1.400 (2)
C2—C3	1.383 (3)	C17—C18	1.377 (2)
C2—H2	0.99 (2)	C17—H17	0.997 (19)
C3—C4	1.388 (3)	C18—C19	1.492 (2)
C3—H3	0.97 (3)	C19—H19A	0.98 (3)
C4—C5	1.380 (3)	C19—H19B	0.97 (3)
C4—H4	0.96 (2)	C19—H19C	0.98 (2)
C5—C6	1.385 (3)	O3—H3A	0.87 (3)
C5—H5	1.00 (2)	O3—H3B	0.94 (3)
C6—H6	1.02 (2)

C7—N1—C8	127.23 (14)	C9—C10—C11	120.29 (14)
C7—N1—H1	115.9 (14)	C9—C10—H10	117.5 (13)
C8—N1—H1	116.9 (14)	C11—C10—H10	122.2 (13)
C14—N2—C13	123.60 (11)	C10—C11—C12	119.52 (15)
C14—N2—H2A	117.1 (11)	C10—C11—H11	121.3 (12)
C13—N2—H2A	117.0 (11)	C12—C11—H11	119.2 (12)
C16—N3—N4	104.44 (11)	C11—C12—C13	120.87 (14)
C18—N4—N3	112.75 (11)	C11—C12—H12	121.0 (10)
C18—N4—H4A	129.2 (13)	C13—C12—H12	118.1 (10)
N3—N4—H4A	117.3 (13)	C12—C13—C8	119.56 (13)
C2—C1—C6	118.94 (16)	C12—C13—N2	117.38 (12)
C2—C1—C7	123.71 (14)	C8—C13—N2	123.06 (13)
C6—C1—C7	117.33 (16)	O2—C14—N2	122.29 (12)
C3—C2—C1	120.71 (16)	O2—C14—C15	121.70 (12)
C3—C2—H2	117.6 (12)	N2—C14—C15	115.99 (12)
C1—C2—H2	121.7 (12)	C16—C15—C14	110.76 (11)
C2—C3—C4	119.9 (2)	C16—C15—H15A	109.7 (11)
C2—C3—H3	120.2 (15)	C14—C15—H15A	106.3 (11)
C4—C3—H3	119.9 (15)	C16—C15—H15B	110.7 (10)
C5—C4—C3	119.85 (19)	C14—C15—H15B	109.5 (10)
C5—C4—H4	123.0 (15)	H15A—C15—H15B	109.7 (15)
C3—C4—H4	117.1 (15)	N3—C16—C17	110.92 (12)
C4—C5—C6	120.57 (16)	N3—C16—C15	119.15 (12)
C4—C5—H5	121.4 (12)	C17—C16—C15	129.92 (13)
C6—C5—H5	118.0 (13)	C18—C17—C16	105.70 (13)
C5—C6—C1	120.03 (18)	C18—C17—H17	129.2 (11)
C5—C6—H6	121.8 (12)	C16—C17—H17	125.0 (11)
C1—C6—H6	118.1 (13)	N4—C18—C17	106.19 (12)
O1—C7—N1	122.37 (16)	N4—C18—C19	120.86 (13)
O1—C7—C1	122.02 (14)	C17—C18—C19	132.95 (14)
N1—C7—C1	115.58 (14)	C18—C19—H19A	112.3 (16)
C9—C8—C13	118.99 (14)	C18—C19—H19B	110.6 (14)
C9—C8—N1	122.09 (14)	H19A—C19—H19B	111 (2)
C13—C8—N1	118.91 (13)	C18—C19—H19C	110.7 (12)
C10—C9—C8	120.75 (15)	H19A—C19—H19C	104 (2)
C10—C9—H9	123.7 (13)	H19B—C19—H19C	108.2 (19)
C8—C9—H9	115.5 (13)	H3A—O3—H3B	107 (2)

C16—N3—N4—C18	0.84 (15)	C11—C12—C13—C8	1.1 (2)
C6—C1—C2—C3	0.1 (3)	C11—C12—C13—N2	−179.58 (13)
C7—C1—C2—C3	−177.84 (16)	C9—C8—C13—C12	−1.9 (2)
C1—C2—C3—C4	0.3 (3)	N1—C8—C13—C12	179.30 (13)
C2—C3—C4—C5	−0.6 (3)	C9—C8—C13—N2	178.78 (14)
C3—C4—C5—C6	0.4 (3)	N1—C8—C13—N2	0.0 (2)
C4—C5—C6—C1	0.1 (3)	C14—N2—C13—C12	120.82 (14)
C2—C1—C6—C5	−0.4 (2)	C14—N2—C13—C8	−59.84 (18)
C7—C1—C6—C5	177.75 (15)	C13—N2—C14—O2	11.49 (19)
C8—N1—C7—O1	−1.2 (3)	C13—N2—C14—C15	−170.30 (11)
C8—N1—C7—C1	176.82 (14)	O2—C14—C15—C16	68.48 (16)
C2—C1—C7—O1	−163.00 (17)	N2—C14—C15—C16	−109.73 (13)
C6—C1—C7—O1	19.0 (2)	N4—N3—C16—C17	−0.49 (15)
C2—C1—C7—N1	19.0 (2)	N4—N3—C16—C15	−179.14 (11)
C6—C1—C7—N1	−159.01 (14)	C14—C15—C16—N3	111.39 (14)
C7—N1—C8—C9	32.0 (2)	C14—C15—C16—C17	−66.96 (18)
C7—N1—C8—C13	−149.26 (15)	N3—C16—C17—C18	0.00 (16)
C13—C8—C9—C10	1.3 (3)	C15—C16—C17—C18	178.46 (13)
N1—C8—C9—C10	−179.91 (15)	N3—N4—C18—C17	−0.86 (16)
C8—C9—C10—C11	0.1 (3)	N3—N4—C18—C19	178.99 (13)
C9—C10—C11—C12	−1.0 (3)	C16—C17—C18—N4	0.50 (16)
C10—C11—C12—C13	0.4 (2)	C16—C17—C18—C19	−179.31 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg3 are the centroids of the N3,N4,C16–C18 and C8–C13 rings respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.88 (2)	2.09 (2)	2.7902 (17)	135.0 (19)
N2—H2A···N3ⁱ	0.95 (2)	1.98 (2)	2.9209 (17)	176.4 (17)
N4—H4A···O3ⁱⁱ	0.92 (2)	1.88 (2)	2.7883 (16)	166.9 (19)
C12—H12···O3ⁱⁱⁱ	0.978 (19)	2.464 (19)	3.4042 (19)	161.2 (14)
O3—H3A···O1	0.87 (3)	1.89 (3)	2.7445 (16)	167 (2)
O3—H3B···O2^iv	0.94 (3)	1.83 (3)	2.7575 (15)	169 (2)
C15—H15A···Cg3^v	0.957 (19)	2.893 (18)	3.8485 (15)	174.0 (14)
C19—H19A···Cg1^vi	0.98 (3)	2.86 (3)	3.645 (2)	138 (2)

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

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
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Volume 2| Part 2| February 2017| x170251

https://doi.org/10.1107/S2414314617002516

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

N-{2-[2-(5-Methyl-1H-pyrazol-3-yl)acetamido]­phen­yl}benzamide monohydrate

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

N-{2-[2-(5-Methyl-1H-pyrazol-3-yl)acetamido]phenyl}benzamide monohydrate