Different mol­ecular conformations co-exist in each of three 2-aryl-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-yl)acetamides: hydrogen bonding in zero, one and two dimensions

Narayana, B.; Yathirajan, H.S.; Rathore, R.S.; Glidewell, C.

doi:10.1107/S2053229616012870

Different molecular conformations co-exist in each of three 2-aryl-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamides: hydrogen bonding in zero, one and two dimensions

B. Narayana, H. S. Yathirajan, R. S. Rathore and C. Glidewell

4-Antipyrine [4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one] and its derivatives exhibit a range of biological activities, including analgesic, antibacterial and anti-inflammatory, and new examples are always of potential interest and value. 2-(4-Chlorophenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide, C₁₉H₁₈ClN₃O₂, (I), crystallizes with Z′ = 2 in the space group P $\overline{1}$ , whereas its positional isomer 2-(2-chlorophenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide, (II), crystallizes with Z′ = 1 in the space group C2/c; the molecules of (II) are disordered over two sets of atomic sites having occupancies of 0.6020 (18) and 0.3980 (18). The two independent molecules of (I) adopt different molecular conformations, as do the two disorder components in (II), where the 2-chlorophenyl substituents adopt different orientations. The molecules of (I) are linked by a combination of N—H

O and C—H

O hydrogen bonds to form centrosymmetric four-molecule aggregates, while those of (II) are linked by the same types of hydrogen bonds forming sheets. The related compound N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-(3-methoxyphenyl)acetamide, C₂₀H₂₁N₃O₃, (III), is isomorphous with (I) but not strictly isostructural; again the two independent molecules adopt different molecular conformations, and the molecules are linked by N—H

O and C—H

O hydrogen bonds to form ribbons. Comparisons are made with some related structures, indicating that a hydrogen-bonded R₂²(10) ring is the common structural motif.

Keywords: synthesis; molecular structure; disorder; molecular conformation; hydrogen bonding; crystal structure; acetamide; pyrazole.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616012870/sk3634sup1.cif Contains datablocks global, I, II
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616012870/sk3634Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616012870/sk3634IIsup3.hkl Contains datablock II
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616012870/sk3634Isup4.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616012870/sk3634IIsup5.cml Supplementary material

CCDC references: 1498397; 1498396

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT-Plus (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(I) 2-(4-Chlorophenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide top

Crystal data top

C₁₉H₁₈ClN₃O₂	Z = 4
M_r = 355.81	F(000) = 744
Triclinic, P1	D_x = 1.347 Mg m⁻³
a = 10.1018 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6099 (5) Å	Cell parameters from 8317 reflections
c = 18.8129 (11) Å	θ = 1.1–28.2°
α = 100.292 (3)°	µ = 0.24 mm⁻¹
β = 91.881 (3)°	T = 295 K
γ = 116.873 (2)°	Block, colourless
V = 1754.78 (15) Å³	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker APEXII area-detector diffractometer	7205 independent reflections
Radiation source: fine-focus sealed tube	5041 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
φ and ω scans	θ_max = 26.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −12→12
T_min = 0.788, T_max = 0.954	k = −13→13
32307 measured reflections	l = −23→23

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.133	w = 1/[σ²(F_o²) + (0.0535P)² + 0.8541P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
7205 reflections	Δρ_max = 0.58 e Å⁻³
461 parameters	Δρ_min = −0.63 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.

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

	x	y	z	U_iso*/U_eq
C11	0.0605 (2)	0.4111 (2)	0.35897 (11)	0.0430 (5)
O11	−0.02706 (17)	0.35666 (18)	0.40064 (9)	0.0587 (4)
N11	0.19775 (19)	0.41816 (17)	0.36076 (9)	0.0393 (4)
H11	0.255 (3)	0.453 (2)	0.3284 (12)	0.047*
C12	0.0218 (3)	0.4743 (2)	0.30052 (14)	0.0545 (6)
H12A	−0.0071	0.5466	0.3224	0.065*
H12B	0.1085	0.5208	0.2760	0.065*
N111	0.2896 (2)	0.27333 (18)	0.50227 (8)	0.0426 (4)
N112	0.33015 (19)	0.20766 (17)	0.44120 (8)	0.0403 (4)
C113	0.2960 (2)	0.2495 (2)	0.37988 (10)	0.0370 (4)
O113	0.30568 (19)	0.19812 (16)	0.31741 (7)	0.0511 (4)
C114	0.2477 (2)	0.35432 (19)	0.40692 (10)	0.0366 (4)
C115	0.2510 (2)	0.3693 (2)	0.48018 (11)	0.0415 (5)
C116	0.3858 (3)	0.3110 (3)	0.57066 (11)	0.0549 (6)
H11A	0.4836	0.3865	0.5682	0.082*
H11B	0.3933	0.2273	0.5784	0.082*
H11C	0.3435	0.3439	0.6103	0.082*
C117	0.2218 (3)	0.4710 (3)	0.53415 (13)	0.0609 (6)
H11D	0.3150	0.5477	0.5600	0.091*
H11E	0.1611	0.4202	0.5680	0.091*
H11F	0.1703	0.5110	0.5094	0.091*
C121	−0.1055 (2)	0.3547 (2)	0.24629 (12)	0.0478 (5)
C122	−0.2525 (3)	0.3030 (3)	0.26009 (13)	0.0568 (6)
H122	−0.2746	0.3487	0.3015	0.068*
C123	−0.3667 (3)	0.1853 (3)	0.21375 (13)	0.0623 (7)
H123	−0.4650	0.1514	0.2238	0.075*
C124	−0.3343 (3)	0.1186 (3)	0.15289 (13)	0.0574 (6)
Cl14	−0.47626 (10)	−0.03248 (9)	0.09513 (4)	0.0943 (3)
C125	−0.1915 (3)	0.1699 (3)	0.13668 (13)	0.0636 (7)
H125	−0.1710	0.1255	0.0943	0.076*
C126	−0.0771 (3)	0.2878 (3)	0.18325 (14)	0.0594 (6)
H126	0.0204	0.3226	0.1720	0.071*
C131	0.3196 (2)	0.0688 (2)	0.43913 (11)	0.0399 (4)
C132	0.2258 (3)	−0.0209 (2)	0.48042 (12)	0.0517 (5)
H132	0.1688	0.0088	0.5101	0.062*
C133	0.2177 (3)	−0.1559 (3)	0.47704 (15)	0.0657 (7)
H133	0.1571	−0.2162	0.5057	0.079*
C134	0.2982 (3)	−0.2006 (3)	0.43200 (16)	0.0695 (7)
H134	0.2911	−0.2918	0.4294	0.083*
C135	0.3892 (3)	−0.1120 (3)	0.39061 (15)	0.0683 (7)
H135	0.4426	−0.1439	0.3594	0.082*
C136	0.4026 (3)	0.0239 (3)	0.39467 (13)	0.0542 (6)
H136	0.4673	0.0851	0.3676	0.065*
C21	0.1899 (2)	0.1687 (2)	0.12171 (13)	0.0476 (5)
O21	0.1859 (2)	0.19074 (18)	0.06084 (9)	0.0670 (5)
N21	0.2985 (2)	0.26017 (18)	0.17678 (10)	0.0444 (4)
H21	0.299 (3)	0.242 (3)	0.2182 (13)	0.053*
C22	0.0736 (3)	0.0327 (2)	0.14195 (15)	0.0583 (6)
H22A	0.0615	0.0549	0.1929	0.070*
H22B	−0.0218	0.0004	0.1131	0.070*
N211	0.6348 (2)	0.54849 (19)	0.14139 (10)	0.0515 (5)
N212	0.59086 (19)	0.62246 (18)	0.19668 (9)	0.0443 (4)
C213	0.4620 (2)	0.5246 (2)	0.21926 (10)	0.0391 (4)
O213	0.40726 (17)	0.55872 (16)	0.27238 (8)	0.0527 (4)
C214	0.4214 (2)	0.3899 (2)	0.17045 (10)	0.0391 (4)
C215	0.5246 (2)	0.4090 (2)	0.12366 (11)	0.0458 (5)
C216	0.7181 (4)	0.6308 (3)	0.08971 (15)	0.0876 (11)
H21A	0.6540	0.6531	0.0613	0.131*
H21B	0.7538	0.5746	0.0580	0.131*
H21C	0.8016	0.7190	0.1156	0.131*
C217	0.5321 (3)	0.3049 (3)	0.06221 (14)	0.0651 (7)
H21D	0.6330	0.3190	0.0628	0.098*
H21E	0.5010	0.3200	0.0171	0.098*
H21F	0.4671	0.2079	0.0668	0.098*
C221	0.1166 (2)	−0.0881 (2)	0.12951 (12)	0.0450 (5)
C222	0.0882 (2)	−0.1749 (2)	0.06067 (12)	0.0485 (5)
H222	0.0452	−0.1566	0.0219	0.058*
C223	0.1228 (2)	−0.2881 (2)	0.04885 (12)	0.0492 (5)
H223	0.1042	−0.3452	0.0023	0.059*
C224	0.1847 (3)	−0.3156 (2)	0.10616 (12)	0.0468 (5)
Cl24	0.22648 (8)	−0.45950 (7)	0.09162 (4)	0.0675 (2)
C225	0.2144 (3)	−0.2317 (3)	0.17520 (12)	0.0540 (6)
H225	0.2562	−0.2515	0.2138	0.065*
C226	0.1811 (3)	−0.1174 (2)	0.18619 (12)	0.0523 (6)
H226	0.2024	−0.0591	0.2326	0.063*
C231	0.7044 (2)	0.7494 (2)	0.24460 (11)	0.0444 (5)
C232	0.8319 (3)	0.7503 (3)	0.27219 (13)	0.0601 (6)
H232	0.8475	0.6699	0.2587	0.072*
C233	0.9370 (3)	0.8729 (4)	0.32045 (15)	0.0794 (9)
H233	1.0248	0.8756	0.3392	0.095*
C234	0.9129 (3)	0.9896 (3)	0.34061 (15)	0.0795 (10)
H234	0.9834	1.0708	0.3739	0.095*
C235	0.7866 (4)	0.9887 (3)	0.31254 (16)	0.0749 (8)
H235	0.7714	1.0693	0.3264	0.090*
C236	0.6803 (3)	0.8674 (2)	0.26328 (13)	0.0583 (6)
H236	0.5942	0.8663	0.2433	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.0410 (11)	0.0343 (10)	0.0495 (12)	0.0144 (9)	0.0053 (9)	0.0084 (9)
O11	0.0444 (9)	0.0690 (10)	0.0657 (10)	0.0240 (8)	0.0183 (8)	0.0263 (8)
N11	0.0394 (9)	0.0358 (9)	0.0434 (9)	0.0155 (7)	0.0108 (7)	0.0151 (7)
C12	0.0465 (13)	0.0462 (12)	0.0732 (16)	0.0207 (11)	0.0031 (11)	0.0221 (11)
N111	0.0517 (10)	0.0448 (9)	0.0316 (8)	0.0232 (8)	0.0060 (7)	0.0067 (7)
N112	0.0505 (10)	0.0397 (9)	0.0339 (8)	0.0230 (8)	0.0086 (7)	0.0096 (7)
C113	0.0387 (10)	0.0339 (10)	0.0354 (10)	0.0130 (8)	0.0076 (8)	0.0104 (8)
O113	0.0757 (11)	0.0528 (9)	0.0352 (8)	0.0376 (8)	0.0142 (7)	0.0118 (6)
C114	0.0363 (10)	0.0320 (9)	0.0371 (10)	0.0119 (8)	0.0060 (8)	0.0078 (8)
C115	0.0443 (11)	0.0365 (10)	0.0384 (11)	0.0152 (9)	0.0066 (9)	0.0050 (8)
C116	0.0614 (14)	0.0546 (13)	0.0390 (11)	0.0204 (12)	−0.0035 (10)	0.0077 (10)
C117	0.0813 (18)	0.0579 (14)	0.0473 (13)	0.0388 (14)	0.0115 (12)	0.0020 (11)
C121	0.0488 (12)	0.0500 (12)	0.0521 (13)	0.0263 (11)	0.0080 (10)	0.0195 (10)
C122	0.0519 (14)	0.0696 (15)	0.0480 (13)	0.0304 (12)	0.0094 (11)	0.0044 (11)
C123	0.0472 (13)	0.0791 (17)	0.0519 (14)	0.0234 (13)	0.0087 (11)	0.0099 (12)
C124	0.0618 (15)	0.0602 (14)	0.0460 (13)	0.0248 (12)	0.0046 (11)	0.0124 (11)
Cl14	0.1013 (6)	0.0752 (5)	0.0688 (5)	0.0169 (4)	−0.0090 (4)	−0.0033 (4)
C125	0.0801 (18)	0.0754 (17)	0.0455 (13)	0.0448 (15)	0.0169 (13)	0.0119 (12)
C126	0.0518 (14)	0.0755 (17)	0.0633 (15)	0.0341 (13)	0.0235 (12)	0.0294 (13)
C131	0.0437 (11)	0.0366 (10)	0.0385 (10)	0.0176 (9)	0.0006 (8)	0.0096 (8)
C132	0.0524 (13)	0.0483 (12)	0.0517 (13)	0.0192 (11)	0.0081 (10)	0.0161 (10)
C133	0.0688 (17)	0.0428 (13)	0.0724 (17)	0.0116 (12)	0.0027 (13)	0.0229 (12)
C134	0.089 (2)	0.0420 (13)	0.0759 (18)	0.0314 (14)	−0.0039 (15)	0.0108 (13)
C135	0.091 (2)	0.0697 (17)	0.0638 (16)	0.0554 (16)	0.0091 (14)	0.0109 (13)
C136	0.0644 (15)	0.0563 (13)	0.0541 (13)	0.0356 (12)	0.0143 (11)	0.0192 (11)
C21	0.0433 (12)	0.0365 (11)	0.0562 (14)	0.0136 (9)	0.0022 (10)	0.0088 (10)
O21	0.0644 (11)	0.0591 (10)	0.0564 (10)	0.0123 (9)	−0.0152 (8)	0.0126 (8)
N21	0.0484 (10)	0.0349 (9)	0.0395 (9)	0.0092 (8)	0.0036 (8)	0.0117 (7)
C22	0.0435 (12)	0.0376 (11)	0.0855 (17)	0.0127 (10)	0.0146 (12)	0.0092 (11)
N211	0.0470 (10)	0.0460 (10)	0.0429 (10)	0.0079 (8)	0.0151 (8)	0.0025 (8)
N212	0.0386 (9)	0.0396 (9)	0.0375 (9)	0.0049 (7)	0.0092 (7)	0.0033 (7)
C213	0.0380 (11)	0.0379 (10)	0.0354 (10)	0.0116 (9)	0.0054 (8)	0.0104 (8)
O213	0.0491 (9)	0.0472 (8)	0.0456 (8)	0.0094 (7)	0.0168 (7)	0.0055 (7)
C214	0.0398 (11)	0.0362 (10)	0.0361 (10)	0.0127 (9)	0.0027 (8)	0.0104 (8)
C215	0.0469 (12)	0.0441 (11)	0.0394 (11)	0.0168 (10)	0.0038 (9)	0.0050 (9)
C216	0.086 (2)	0.0715 (18)	0.0609 (16)	−0.0004 (16)	0.0385 (15)	0.0074 (14)
C217	0.0706 (17)	0.0587 (15)	0.0564 (15)	0.0265 (13)	0.0134 (12)	−0.0007 (12)
C221	0.0347 (10)	0.0320 (10)	0.0564 (13)	0.0050 (8)	0.0115 (9)	0.0096 (9)
C222	0.0465 (12)	0.0457 (12)	0.0472 (12)	0.0155 (10)	0.0029 (9)	0.0131 (10)
C223	0.0520 (13)	0.0463 (12)	0.0408 (11)	0.0178 (10)	0.0053 (10)	0.0037 (9)
C224	0.0511 (13)	0.0412 (11)	0.0464 (12)	0.0192 (10)	0.0087 (10)	0.0115 (9)
Cl24	0.0870 (5)	0.0629 (4)	0.0687 (4)	0.0460 (4)	0.0189 (3)	0.0202 (3)
C225	0.0606 (14)	0.0558 (14)	0.0426 (12)	0.0232 (12)	0.0056 (10)	0.0148 (10)
C226	0.0554 (13)	0.0452 (12)	0.0440 (12)	0.0151 (11)	0.0084 (10)	0.0034 (9)
C231	0.0395 (11)	0.0389 (11)	0.0371 (10)	0.0030 (9)	0.0103 (9)	0.0079 (8)
C232	0.0476 (14)	0.0649 (15)	0.0559 (14)	0.0200 (12)	0.0045 (11)	0.0023 (12)
C233	0.0410 (14)	0.100 (2)	0.0605 (16)	0.0094 (15)	0.0014 (12)	−0.0040 (16)
C234	0.0570 (17)	0.0640 (18)	0.0588 (16)	−0.0143 (14)	0.0115 (13)	−0.0083 (13)
C235	0.087 (2)	0.0383 (13)	0.0740 (18)	0.0097 (14)	0.0189 (16)	0.0042 (12)
C236	0.0616 (15)	0.0444 (13)	0.0578 (14)	0.0148 (11)	0.0101 (11)	0.0122 (11)

Geometric parameters (Å, º) top

C11—O11	1.215 (2)	C21—O21	1.212 (3)
C11—N11	1.353 (3)	C21—N21	1.350 (3)
C11—C12	1.511 (3)	C21—C22	1.517 (3)
N11—C114	1.399 (3)	N21—C214	1.405 (2)
N11—H11	0.87 (2)	N21—H21	0.83 (2)
C12—C121	1.510 (3)	C22—C221	1.512 (3)
C12—H12A	0.9700	C22—H22A	0.9700
C12—H12B	0.9700	C22—H22B	0.9700
N111—C115	1.364 (3)	N211—C215	1.360 (3)
N111—N112	1.406 (2)	N211—N212	1.396 (2)
N111—C116	1.463 (3)	N211—C216	1.452 (3)
N112—C113	1.394 (2)	N212—C213	1.387 (2)
N112—C131	1.422 (3)	N212—C231	1.430 (2)
C113—O113	1.231 (2)	C213—O213	1.235 (2)
C113—C114	1.428 (3)	C213—C214	1.425 (3)
C114—C115	1.356 (3)	C214—C215	1.355 (3)
C115—C117	1.483 (3)	C215—C217	1.479 (3)
C116—H11A	0.9600	C216—H21A	0.9600
C116—H11B	0.9600	C216—H21B	0.9600
C116—H11C	0.9600	C216—H21C	0.9600
C117—H11D	0.9600	C217—H21D	0.9600
C117—H11E	0.9600	C217—H21E	0.9600
C117—H11F	0.9600	C217—H21F	0.9600
C121—C126	1.378 (3)	C221—C226	1.383 (3)
C121—C122	1.383 (3)	C221—C222	1.385 (3)
C122—C123	1.376 (3)	C222—C223	1.380 (3)
C122—H122	0.9300	C222—H222	0.9300
C123—C124	1.365 (3)	C223—C224	1.368 (3)
C123—H123	0.9300	C223—H223	0.9300
C124—C125	1.360 (4)	C224—C225	1.374 (3)
C124—Cl14	1.733 (3)	C224—Cl24	1.740 (2)
C125—C126	1.380 (4)	C225—C226	1.382 (3)
C125—H125	0.9300	C225—H225	0.9300
C126—H126	0.9300	C226—H226	0.9300
C131—C136	1.376 (3)	C231—C232	1.368 (3)
C131—C132	1.380 (3)	C231—C236	1.369 (3)
C132—C133	1.387 (3)	C232—C233	1.382 (4)
C132—H132	0.9300	C232—H232	0.9300
C133—C134	1.361 (4)	C233—C234	1.359 (5)
C133—H133	0.9300	C233—H233	0.9300
C134—C135	1.365 (4)	C234—C235	1.361 (5)
C134—H134	0.9300	C234—H234	0.9300
C135—C136	1.373 (3)	C235—C236	1.388 (4)
C135—H135	0.9300	C235—H235	0.9300
C136—H136	0.9300	C236—H236	0.9300

O11—C11—N11	122.9 (2)	O21—C21—N21	123.5 (2)
O11—C11—C12	121.8 (2)	O21—C21—C22	122.3 (2)
N11—C11—C12	115.31 (18)	N21—C21—C22	114.1 (2)
C11—N11—C114	123.23 (17)	C21—N21—C214	124.54 (18)
C11—N11—H11	120.1 (15)	C21—N21—H21	121.6 (16)
C114—N11—H11	116.2 (15)	C214—N21—H21	113.9 (16)
C121—C12—C11	109.27 (17)	C221—C22—C21	112.18 (18)
C121—C12—H12A	109.8	C221—C22—H22A	109.2
C11—C12—H12A	109.8	C21—C22—H22A	109.2
C121—C12—H12B	109.8	C221—C22—H22B	109.2
C11—C12—H12B	109.8	C21—C22—H22B	109.2
H12A—C12—H12B	108.3	H22A—C22—H22B	107.9
C115—N111—N112	106.81 (15)	C215—N211—N212	107.21 (16)
C115—N111—C116	121.99 (17)	C215—N211—C216	125.02 (19)
N112—N111—C116	114.89 (18)	N212—N211—C216	116.1 (2)
C113—N112—N111	108.88 (16)	C213—N212—N211	109.36 (15)
C113—N112—C131	123.24 (16)	C213—N212—C231	123.33 (16)
N111—N112—C131	118.59 (15)	N211—N212—C231	118.30 (16)
O113—C113—N112	123.48 (18)	O213—C213—N212	122.90 (18)
O113—C113—C114	131.26 (18)	O213—C213—C214	132.45 (18)
N112—C113—C114	105.24 (16)	N212—C213—C214	104.62 (17)
C115—C114—N11	129.18 (19)	C215—C214—N21	128.16 (19)
C115—C114—C113	108.43 (18)	C215—C214—C213	109.06 (17)
N11—C114—C113	122.26 (17)	N21—C214—C213	122.61 (18)
C114—C115—N111	110.00 (17)	C214—C215—N211	109.27 (18)
C114—C115—C117	129.6 (2)	C214—C215—C217	130.3 (2)
N111—C115—C117	120.36 (19)	N211—C215—C217	120.4 (2)
N111—C116—H11A	109.5	N211—C216—H21A	109.5
N111—C116—H11B	109.5	N211—C216—H21B	109.5
H11A—C116—H11B	109.5	H21A—C216—H21B	109.5
N111—C116—H11C	109.5	N211—C216—H21C	109.5
H11A—C116—H11C	109.5	H21A—C216—H21C	109.5
H11B—C116—H11C	109.5	H21B—C216—H21C	109.5
C115—C117—H11D	109.5	C215—C217—H21D	109.5
C115—C117—H11E	109.5	C215—C217—H21E	109.5
H11D—C117—H11E	109.5	H21D—C217—H21E	109.5
C115—C117—H11F	109.5	C215—C217—H21F	109.5
H11D—C117—H11F	109.5	H21D—C217—H21F	109.5
H11E—C117—H11F	109.5	H21E—C217—H21F	109.5
C126—C121—C122	118.0 (2)	C226—C221—C222	118.4 (2)
C126—C121—C12	120.4 (2)	C226—C221—C22	121.4 (2)
C122—C121—C12	121.5 (2)	C222—C221—C22	120.2 (2)
C123—C122—C121	121.3 (2)	C223—C222—C221	120.9 (2)
C123—C122—H122	119.4	C223—C222—H222	119.5
C121—C122—H122	119.4	C221—C222—H222	119.5
C124—C123—C122	119.3 (2)	C224—C223—C222	119.4 (2)
C124—C123—H123	120.3	C224—C223—H223	120.3
C122—C123—H123	120.3	C222—C223—H223	120.3
C125—C124—C123	120.7 (2)	C223—C224—C225	121.3 (2)
C125—C124—Cl14	119.4 (2)	C223—C224—Cl24	119.50 (17)
C123—C124—Cl14	119.9 (2)	C225—C224—Cl24	119.24 (18)
C124—C125—C126	119.9 (2)	C224—C225—C226	118.8 (2)
C124—C125—H125	120.1	C224—C225—H225	120.6
C126—C125—H125	120.1	C226—C225—H225	120.6
C121—C126—C125	120.8 (2)	C225—C226—C221	121.3 (2)
C121—C126—H126	119.6	C225—C226—H226	119.4
C125—C126—H126	119.6	C221—C226—H226	119.4
C136—C131—C132	120.3 (2)	C232—C231—C236	121.3 (2)
C136—C131—N112	119.24 (18)	C232—C231—N212	120.3 (2)
C132—C131—N112	120.46 (19)	C236—C231—N212	118.4 (2)
C131—C132—C133	119.1 (2)	C231—C232—C233	118.8 (3)
C131—C132—H132	120.5	C231—C232—H232	120.6
C133—C132—H132	120.5	C233—C232—H232	120.6
C134—C133—C132	120.3 (2)	C234—C233—C232	120.4 (3)
C134—C133—H133	119.9	C234—C233—H233	119.8
C132—C133—H133	119.9	C232—C233—H233	119.8
C133—C134—C135	120.3 (2)	C233—C234—C235	120.6 (2)
C133—C134—H134	119.9	C233—C234—H234	119.7
C135—C134—H134	119.9	C235—C234—H234	119.7
C134—C135—C136	120.5 (3)	C234—C235—C236	120.0 (3)
C134—C135—H135	119.7	C234—C235—H235	120.0
C136—C135—H135	119.7	C236—C235—H235	120.0
C135—C136—C131	119.5 (2)	C231—C236—C235	118.8 (3)
C135—C136—H136	120.2	C231—C236—H236	120.6
C131—C136—H136	120.2	C235—C236—H236	120.6

O11—C11—N11—C114	4.9 (3)	O21—C21—N21—C214	−1.4 (4)
C12—C11—N11—C114	−174.36 (18)	C22—C21—N21—C214	177.29 (19)
O11—C11—C12—C121	−65.0 (3)	O21—C21—C22—C221	89.4 (3)
N11—C11—C12—C121	114.3 (2)	N21—C21—C22—C221	−89.3 (3)
C115—N111—N112—C113	−8.2 (2)	C215—N211—N212—C213	7.2 (2)
C116—N111—N112—C113	−146.82 (17)	C216—N211—N212—C213	152.4 (2)
C115—N111—N112—C131	−155.98 (17)	C215—N211—N212—C231	155.52 (19)
C116—N111—N112—C131	65.4 (2)	C216—N211—N212—C231	−59.3 (3)
N111—N112—C113—O113	−172.76 (18)	N211—N212—C213—O213	172.7 (2)
C131—N112—C113—O113	−26.8 (3)	C231—N212—C213—O213	26.3 (3)
N111—N112—C113—C114	5.8 (2)	N211—N212—C213—C214	−5.5 (2)
C131—N112—C113—C114	151.75 (18)	C231—N212—C213—C214	−151.9 (2)
C11—N11—C114—C115	−53.2 (3)	C21—N21—C214—C215	−56.2 (3)
C11—N11—C114—C113	122.2 (2)	C21—N21—C214—C213	129.1 (2)
O113—C113—C114—C115	177.1 (2)	O213—C213—C214—C215	−176.1 (2)
N112—C113—C114—C115	−1.3 (2)	N212—C213—C214—C215	1.8 (2)
O113—C113—C114—N11	0.9 (3)	O213—C213—C214—N21	−0.5 (4)
N112—C113—C114—N11	−177.47 (16)	N212—C213—C214—N21	177.38 (18)
N11—C114—C115—N111	171.97 (18)	N21—C214—C215—N211	−172.6 (2)
C113—C114—C115—N111	−3.9 (2)	C213—C214—C215—N211	2.6 (3)
N11—C114—C115—C117	−8.9 (4)	N21—C214—C215—C217	6.2 (4)
C113—C114—C115—C117	175.3 (2)	C213—C214—C215—C217	−178.5 (2)
N112—N111—C115—C114	7.4 (2)	N212—N211—C215—C214	−6.0 (2)
C116—N111—C115—C114	142.4 (2)	C216—N211—C215—C214	−147.2 (3)
N112—N111—C115—C117	−171.84 (19)	N212—N211—C215—C217	175.0 (2)
C116—N111—C115—C117	−36.8 (3)	C216—N211—C215—C217	33.8 (4)
C11—C12—C121—C126	−95.2 (3)	C21—C22—C221—C226	99.2 (3)
C11—C12—C121—C122	80.8 (3)	C21—C22—C221—C222	−82.5 (3)
C126—C121—C122—C123	2.2 (4)	C226—C221—C222—C223	0.2 (3)
C12—C121—C122—C123	−173.9 (2)	C22—C221—C222—C223	−178.14 (19)
C121—C122—C123—C124	−0.2 (4)	C221—C222—C223—C224	0.6 (3)
C122—C123—C124—C125	−1.9 (4)	C222—C223—C224—C225	−0.6 (3)
C122—C123—C124—Cl14	178.4 (2)	C222—C223—C224—Cl24	179.27 (17)
C123—C124—C125—C126	2.0 (4)	C223—C224—C225—C226	−0.2 (3)
Cl14—C124—C125—C126	−178.3 (2)	Cl24—C224—C225—C226	179.87 (17)
C122—C121—C126—C125	−2.1 (4)	C224—C225—C226—C221	1.1 (3)
C12—C121—C126—C125	174.0 (2)	C222—C221—C226—C225	−1.1 (3)
C124—C125—C126—C121	0.0 (4)	C22—C221—C226—C225	177.2 (2)
C113—N112—C131—C136	58.8 (3)	C213—N212—C231—C232	99.7 (3)
N111—N112—C131—C136	−158.29 (19)	N211—N212—C231—C232	−43.9 (3)
C113—N112—C131—C132	−120.3 (2)	C213—N212—C231—C236	−78.7 (3)
N111—N112—C131—C132	22.6 (3)	N211—N212—C231—C236	137.7 (2)
C136—C131—C132—C133	0.7 (3)	C236—C231—C232—C233	0.7 (3)
N112—C131—C132—C133	179.8 (2)	N212—C231—C232—C233	−177.7 (2)
C131—C132—C133—C134	−1.8 (4)	C231—C232—C233—C234	0.7 (4)
C132—C133—C134—C135	1.0 (4)	C232—C233—C234—C235	−1.3 (4)
C133—C134—C135—C136	1.0 (4)	C233—C234—C235—C236	0.5 (4)
C134—C135—C136—C131	−2.1 (4)	C232—C231—C236—C235	−1.5 (3)
C132—C131—C136—C135	1.2 (3)	N212—C231—C236—C235	176.9 (2)
N112—C131—C136—C135	−177.9 (2)	C234—C235—C236—C231	0.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O213	0.87 (3)	1.93 (2)	2.781 (2)	169 (2)
N21—H21···O113	0.84 (2)	2.01 (2)	2.845 (2)	178 (4)
C133—H133···O11ⁱ	0.93	2.52	3.446 (3)	171

Symmetry code: (i) −x, −y, −z+1.

(II) 2-(2-Chlorophenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide top

Crystal data top

C₁₉H₁₈ClN₃O₂	F(000) = 1488
M_r = 355.81	D_x = 1.336 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.023 (3) Å	Cell parameters from 6192 reflections
b = 8.2976 (10) Å	θ = 2.1–32.2°
c = 21.602 (3) Å	µ = 0.23 mm⁻¹
β = 120.957 (14)°	T = 295 K
V = 3538.9 (9) Å³	Block, colourless
Z = 8	0.40 × 0.30 × 0.20 mm

Data collection top

Bruker APEXII area-detector diffractometer	4079 independent reflections
Radiation source: fine-focus sealed tube	3038 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 27.6°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −29→29
T_min = 0.767, T_max = 0.954	k = −8→10
33715 measured reflections	l = −28→28

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.0639P)² + 3.3163P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.149	(Δ/σ)_max = 0.007
S = 1.03	Δρ_max = 0.30 e Å⁻³
4079 reflections	Δρ_min = −0.41 e Å⁻³
319 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
64 restraints	Extinction coefficient: 0.0042 (5)

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C11	0.5797 (2)	0.6114 (5)	0.3652 (2)	0.0430 (10)	0.6020 (18)
O11	0.6397 (10)	0.563 (3)	0.404 (2)	0.093 (3)	0.6020 (18)
N11	0.5674 (5)	0.7661 (13)	0.3420 (9)	0.0447 (8)	0.6020 (18)
H11	0.532 (3)	0.811 (7)	0.332 (3)	0.054*	0.6020 (18)
C12	0.51822 (15)	0.5266 (4)	0.3591 (2)	0.0521 (7)	0.6020 (18)
H12A	0.4917	0.6049	0.3675	0.063*	0.6020 (18)
H12B	0.4902	0.4862	0.3103	0.063*	0.6020 (18)
N111	0.7060 (7)	1.016 (3)	0.3680 (6)	0.0452 (7)	0.6020 (18)
N112	0.6676 (5)	1.0041 (18)	0.2923 (6)	0.0418 (9)	0.6020 (18)
C113	0.6138 (4)	0.8990 (11)	0.2722 (5)	0.0327 (15)	0.6020 (18)
O113	0.5739 (5)	0.8552 (12)	0.2095 (5)	0.0432 (15)	0.6020 (18)
C114	0.6156 (6)	0.8630 (13)	0.3379 (5)	0.0365 (13)	0.6020 (18)
C115	0.6693 (13)	0.939 (5)	0.3931 (5)	0.0435 (6)	0.6020 (18)
C116	0.734 (2)	1.177 (4)	0.3956 (12)	0.0678 (8)	0.6020 (18)
H11A	0.7651	1.1711	0.4467	0.102*	0.6020 (18)
H11B	0.6974	1.2492	0.3863	0.102*	0.6020 (18)
H11C	0.7566	1.2161	0.3720	0.102*	0.6020 (18)
C117	0.6917 (11)	0.943 (3)	0.4710 (5)	0.0647 (10)	0.6020 (18)
H11D	0.6630	0.8747	0.4797	0.097*	0.6020 (18)
H11E	0.6889	1.0517	0.4848	0.097*	0.6020 (18)
H11F	0.7377	0.9062	0.4990	0.097*	0.6020 (18)
C121	0.5354 (3)	0.3900 (4)	0.41070 (17)	0.0420 (10)	0.6020 (18)
C122	0.5669 (4)	0.4185 (6)	0.4834 (2)	0.0549 (11)	0.6020 (18)
C123	0.5817 (8)	0.2935 (9)	0.5341 (3)	0.0690 (13)	0.6020 (18)
H123	0.6027	0.3151	0.5832	0.083*	0.6020 (18)
C124	0.5641 (15)	0.1393 (9)	0.5081 (4)	0.0723 (14)	0.6020 (18)
H124	0.5723	0.0553	0.5401	0.087*	0.6020 (18)
C125	0.5348 (10)	0.1072 (6)	0.4367 (4)	0.0722 (13)	0.6020 (18)
H125	0.5256	0.0011	0.4205	0.087*	0.6020 (18)
C126	0.5187 (4)	0.2301 (5)	0.3883 (3)	0.0604 (11)	0.6020 (18)
H126	0.4961	0.2066	0.3392	0.073*	0.6020 (18)
C131	0.7008 (5)	1.034 (3)	0.2530 (7)	0.0450 (5)	0.6020 (18)
C132	0.7707 (5)	1.0201 (12)	0.2868 (6)	0.0567 (18)	0.6020 (18)
H132	0.7963	0.9930	0.3355	0.068*	0.6020 (18)
C133	0.8017 (6)	1.047 (2)	0.2473 (9)	0.077 (3)	0.6020 (18)
H133	0.8481	1.0310	0.2688	0.092*	0.6020 (18)
C134	0.7653 (8)	1.0974 (18)	0.1777 (8)	0.076 (2)	0.6020 (18)
H134	0.7866	1.1159	0.1516	0.091*	0.6020 (18)
C135	0.6974 (9)	1.120 (4)	0.1464 (7)	0.075 (3)	0.6020 (18)
H135	0.6730	1.1608	0.0997	0.091*	0.6020 (18)
C136	0.6634 (8)	1.084 (4)	0.1829 (8)	0.0616 (14)	0.6020 (18)
H136	0.6166	1.0947	0.1601	0.074*	0.6020 (18)
Cl12	0.59006 (6)	0.6106 (2)	0.51896 (6)	0.0847 (4)	0.6020 (18)
C21	0.5859 (3)	0.6482 (9)	0.3872 (4)	0.0430 (10)	0.3980 (18)
O21	0.6348 (15)	0.564 (4)	0.395 (4)	0.093 (3)	0.3980 (18)
N21	0.5662 (7)	0.779 (2)	0.3433 (13)	0.0447 (8)	0.3980 (18)
H21	0.520 (4)	0.793 (11)	0.317 (4)	0.054*	0.3980 (18)
C22	0.5300 (2)	0.5857 (6)	0.3992 (3)	0.0521 (7)	0.3980 (18)
H22A	0.5240	0.6613	0.4297	0.063*	0.3980 (18)
H22B	0.4878	0.5817	0.3531	0.063*	0.3980 (18)
N211	0.7063 (11)	1.023 (4)	0.3698 (9)	0.0452 (7)	0.3980 (18)
N212	0.6664 (8)	1.018 (3)	0.2941 (8)	0.0418 (9)	0.3980 (18)
C213	0.6083 (7)	0.928 (2)	0.2732 (7)	0.0327 (15)	0.3980 (18)
O213	0.5674 (8)	0.887 (2)	0.2103 (8)	0.0432 (15)	0.3980 (18)
C214	0.6123 (10)	0.884 (2)	0.3393 (8)	0.0365 (13)	0.3980 (18)
C215	0.6706 (19)	0.943 (7)	0.3952 (8)	0.0435 (6)	0.3980 (18)
C216	0.736 (3)	1.181 (6)	0.3999 (18)	0.0678 (8)	0.3980 (18)
H21A	0.7561	1.2248	0.3745	0.102*	0.3980 (18)
H21B	0.7694	1.1699	0.4501	0.102*	0.3980 (18)
H21C	0.7006	1.2526	0.3949	0.102*	0.3980 (18)
C217	0.6953 (16)	0.939 (5)	0.4738 (8)	0.0647 (10)	0.3980 (18)
H21D	0.6740	1.0236	0.4853	0.097*	0.3980 (18)
H21E	0.7435	0.9541	0.5007	0.097*	0.3980 (18)
H21F	0.6844	0.8367	0.4861	0.097*	0.3980 (18)
C221	0.5440 (5)	0.4227 (7)	0.4331 (4)	0.0420 (10)	0.3980 (18)
C222	0.5713 (7)	0.4054 (11)	0.5057 (4)	0.0549 (11)	0.3980 (18)
H222	0.5848	0.4970	0.5346	0.066*	0.3980 (18)
C223	0.5797 (14)	0.2525 (14)	0.5387 (5)	0.0690 (13)	0.3980 (18)
H223	0.5995	0.2424	0.5884	0.083*	0.3980 (18)
C224	0.558 (2)	0.1199 (13)	0.4944 (7)	0.0723 (14)	0.3980 (18)
H224	0.5629	0.0180	0.5146	0.087*	0.3980 (18)
C225	0.5279 (16)	0.1345 (10)	0.4219 (7)	0.0722 (13)	0.3980 (18)
H225	0.5089	0.0448	0.3923	0.087*	0.3980 (18)
C226	0.5260 (8)	0.2811 (9)	0.3921 (4)	0.0604 (11)	0.3980 (18)
C231	0.6996 (7)	1.036 (5)	0.2540 (10)	0.0450 (5)	0.3980 (18)
C232	0.7656 (8)	0.982 (2)	0.2826 (10)	0.0567 (18)	0.3980 (18)
H232	0.7876	0.9274	0.3265	0.068*	0.3980 (18)
C233	0.7983 (10)	1.010 (4)	0.2448 (14)	0.077 (3)	0.3980 (18)
H233	0.8447	0.9931	0.2671	0.092*	0.3980 (18)
C234	0.7630 (13)	1.062 (3)	0.1754 (13)	0.076 (2)	0.3980 (18)
H234	0.7846	1.0769	0.1494	0.091*	0.3980 (18)
C235	0.6956 (13)	1.093 (6)	0.1443 (11)	0.075 (3)	0.3980 (18)
H235	0.6702	1.1153	0.0951	0.091*	0.3980 (18)
C236	0.6638 (11)	1.093 (7)	0.1849 (12)	0.0616 (14)	0.3980 (18)
H236	0.6197	1.1306	0.1654	0.074*	0.3980 (18)
Cl26	0.4895 (2)	0.2868 (4)	0.2999 (2)	0.1328 (11)	0.3980 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.0348 (12)	0.049 (2)	0.050 (3)	−0.0007 (12)	0.0253 (18)	0.0039 (16)
O11	0.043 (2)	0.0891 (13)	0.151 (9)	0.0239 (15)	0.053 (5)	0.066 (2)
N11	0.0298 (7)	0.0521 (17)	0.0548 (10)	0.0040 (8)	0.0236 (7)	0.0137 (14)
C12	0.0339 (12)	0.060 (2)	0.0599 (19)	−0.0029 (12)	0.0222 (15)	0.0149 (14)
N111	0.0397 (7)	0.0557 (18)	0.0398 (9)	−0.0131 (8)	0.0201 (7)	−0.0099 (8)
N112	0.0371 (7)	0.051 (2)	0.0396 (9)	−0.0126 (10)	0.0211 (6)	−0.0059 (10)
C113	0.0284 (15)	0.029 (4)	0.0435 (9)	0.003 (2)	0.0202 (9)	−0.0015 (16)
O113	0.0343 (18)	0.052 (4)	0.0404 (7)	−0.007 (2)	0.0170 (9)	−0.0066 (18)
C114	0.0312 (12)	0.038 (3)	0.0442 (9)	0.0035 (18)	0.0222 (8)	0.0033 (13)
C115	0.0362 (11)	0.0553 (19)	0.0418 (10)	0.0001 (8)	0.0221 (10)	−0.0007 (12)
C116	0.066 (2)	0.070 (2)	0.067 (3)	−0.0303 (13)	0.033 (3)	−0.0273 (16)
C117	0.050 (2)	0.1021 (19)	0.0416 (12)	−0.003 (2)	0.0234 (13)	−0.0033 (14)
C121	0.0298 (16)	0.051 (2)	0.042 (2)	−0.0077 (15)	0.017 (2)	0.0010 (18)
C122	0.0437 (16)	0.0665 (17)	0.054 (3)	−0.0084 (13)	0.025 (3)	0.004 (2)
C123	0.0453 (15)	0.098 (4)	0.0595 (15)	−0.005 (4)	0.0238 (14)	0.0260 (19)
C124	0.051 (5)	0.068 (2)	0.086 (3)	0.000 (3)	0.027 (6)	0.029 (2)
C125	0.069 (4)	0.047 (2)	0.092 (4)	0.009 (4)	0.036 (5)	0.014 (2)
C126	0.053 (2)	0.066 (3)	0.0685 (16)	−0.011 (3)	0.0349 (15)	0.004 (2)
C131	0.0470 (9)	0.0461 (11)	0.0512 (10)	−0.0155 (8)	0.0320 (8)	−0.0093 (8)
C132	0.0483 (17)	0.055 (5)	0.0749 (18)	−0.014 (3)	0.0372 (15)	−0.005 (3)
C133	0.0643 (18)	0.082 (9)	0.111 (2)	−0.022 (3)	0.0634 (19)	−0.019 (4)
C134	0.105 (2)	0.066 (7)	0.102 (2)	−0.050 (4)	0.086 (2)	−0.041 (3)
C135	0.101 (2)	0.087 (9)	0.0580 (14)	−0.037 (3)	0.0546 (15)	−0.018 (3)
C136	0.0594 (12)	0.083 (4)	0.0477 (12)	−0.0184 (13)	0.0316 (10)	−0.0078 (18)
Cl12	0.0808 (7)	0.0924 (8)	0.0814 (7)	−0.0292 (6)	0.0420 (6)	−0.0263 (6)
C21	0.0348 (12)	0.049 (2)	0.050 (3)	−0.0007 (12)	0.0253 (18)	0.0039 (16)
O21	0.043 (2)	0.0891 (13)	0.151 (9)	0.0239 (15)	0.053 (5)	0.066 (2)
N21	0.0298 (7)	0.0521 (17)	0.0548 (10)	0.0040 (8)	0.0236 (7)	0.0137 (14)
C22	0.0339 (12)	0.060 (2)	0.0599 (19)	−0.0029 (12)	0.0222 (15)	0.0149 (14)
N211	0.0397 (7)	0.0557 (18)	0.0398 (9)	−0.0131 (8)	0.0201 (7)	−0.0099 (8)
N212	0.0371 (7)	0.051 (2)	0.0396 (9)	−0.0126 (10)	0.0211 (6)	−0.0059 (10)
C213	0.0284 (15)	0.029 (4)	0.0435 (9)	0.003 (2)	0.0202 (9)	−0.0015 (16)
O213	0.0343 (18)	0.052 (4)	0.0404 (7)	−0.007 (2)	0.0170 (9)	−0.0066 (18)
C214	0.0312 (12)	0.038 (3)	0.0442 (9)	0.0035 (18)	0.0222 (8)	0.0033 (13)
C215	0.0362 (11)	0.0553 (19)	0.0418 (10)	0.0001 (8)	0.0221 (10)	−0.0007 (12)
C216	0.066 (2)	0.070 (2)	0.067 (3)	−0.0303 (13)	0.033 (3)	−0.0273 (16)
C217	0.050 (2)	0.1021 (19)	0.0416 (12)	−0.003 (2)	0.0234 (13)	−0.0033 (14)
C221	0.0298 (16)	0.051 (2)	0.042 (2)	−0.0077 (15)	0.017 (2)	0.0010 (18)
C222	0.0437 (16)	0.0665 (17)	0.054 (3)	−0.0084 (13)	0.025 (3)	0.004 (2)
C223	0.0453 (15)	0.098 (4)	0.0595 (15)	−0.005 (4)	0.0238 (14)	0.0260 (19)
C224	0.051 (5)	0.068 (2)	0.086 (3)	0.000 (3)	0.027 (6)	0.029 (2)
C225	0.069 (4)	0.047 (2)	0.092 (4)	0.009 (4)	0.036 (5)	0.014 (2)
C226	0.053 (2)	0.066 (3)	0.0685 (16)	−0.011 (3)	0.0349 (15)	0.004 (2)
C231	0.0470 (9)	0.0461 (11)	0.0512 (10)	−0.0155 (8)	0.0320 (8)	−0.0093 (8)
C232	0.0483 (17)	0.055 (5)	0.0749 (18)	−0.014 (3)	0.0372 (15)	−0.005 (3)
C233	0.0643 (18)	0.082 (9)	0.111 (2)	−0.022 (3)	0.0634 (19)	−0.019 (4)
C234	0.105 (2)	0.066 (7)	0.102 (2)	−0.050 (4)	0.086 (2)	−0.041 (3)
C235	0.101 (2)	0.087 (9)	0.0580 (14)	−0.037 (3)	0.0546 (15)	−0.018 (3)
C236	0.0594 (12)	0.083 (4)	0.0477 (12)	−0.0184 (13)	0.0316 (10)	−0.0078 (18)
Cl26	0.150 (2)	0.183 (3)	0.0636 (11)	−0.0293 (19)	0.0536 (13)	0.0027 (13)

Geometric parameters (Å, º) top

C11—O11	1.257 (15)	C21—O21	1.258 (16)
C11—N11	1.353 (5)	C21—N21	1.355 (5)
C11—C12	1.524 (3)	C21—C22	1.528 (4)
N11—C114	1.410 (3)	N21—C214	1.410 (3)
N11—H11	0.82 (7)	N21—H21	0.91 (8)
C12—C121	1.493 (3)	C22—C221	1.492 (4)
C12—H12A	0.9700	C22—H22A	0.9700
C12—H12B	0.9700	C22—H22B	0.9700
N111—C115	1.373 (3)	N211—C215	1.373 (4)
N111—N112	1.407 (3)	N211—N212	1.406 (4)
N111—C116	1.467 (3)	N211—C216	1.467 (4)
N112—C113	1.389 (3)	N212—C213	1.389 (4)
N112—C131	1.427 (3)	N212—C231	1.427 (4)
C113—O113	1.237 (3)	C213—O213	1.237 (3)
C113—C114	1.430 (3)	C213—C214	1.430 (4)
C114—C115	1.353 (5)	C214—C215	1.353 (5)
C115—C117	1.487 (4)	C215—C217	1.487 (4)
C116—H11A	0.9600	C216—H21A	0.9600
C116—H11B	0.9600	C216—H21B	0.9600
C116—H11C	0.9600	C216—H21C	0.9600
C117—H11D	0.9600	C217—H21D	0.9600
C117—H11E	0.9600	C217—H21E	0.9600
C117—H11F	0.9600	C217—H21F	0.9600
C121—C122	1.370 (4)	C221—C222	1.365 (5)
C121—C126	1.397 (4)	C221—C226	1.399 (5)
C122—C123	1.417 (4)	C222—C223	1.418 (5)
C122—Cl12	1.730 (5)	C222—H222	0.9300
C123—C124	1.372 (5)	C223—C224	1.372 (5)
C123—H123	0.9300	C223—H223	0.9300
C124—C125	1.354 (5)	C224—C225	1.355 (5)
C124—H124	0.9300	C224—H224	0.9300
C125—C126	1.368 (5)	C225—C226	1.366 (5)
C125—H125	0.9300	C225—H225	0.9300
C126—H126	0.9300	C226—Cl26	1.719 (7)
C131—C136	1.366 (4)	C231—C236	1.366 (4)
C131—C132	1.388 (5)	C231—C232	1.388 (6)
C132—C133	1.385 (4)	C232—C233	1.386 (5)
C132—H132	0.9300	C232—H232	0.9300
C133—C134	1.356 (5)	C233—C234	1.357 (5)
C133—H133	0.9300	C233—H233	0.9300
C134—C135	1.360 (5)	C234—C235	1.360 (5)
C134—H134	0.9300	C234—H234	0.9300
C135—C136	1.401 (7)	C235—C236	1.402 (8)
C135—H135	0.9300	C235—H235	0.9300
C136—H136	0.9300	C236—H236	0.9300

O11—C11—N11	119.8 (9)	O21—C21—N21	119.6 (12)
O11—C11—C12	124.4 (4)	O21—C21—C22	124.0 (6)
N11—C11—C12	113.4 (3)	N21—C21—C22	112.5 (4)
C11—N11—C114	122.9 (5)	C21—N21—C214	123.1 (6)
C11—N11—H11	121 (4)	C21—N21—H21	114 (6)
C114—N11—H11	116 (4)	C214—N21—H21	123 (6)
C121—C12—C11	114.1 (3)	C221—C22—C21	113.8 (4)
C121—C12—H12A	108.7	C221—C22—H22A	108.8
C11—C12—H12A	108.7	C21—C22—H22A	108.8
C121—C12—H12B	108.7	C221—C22—H22B	108.8
C11—C12—H12B	108.7	C21—C22—H22B	108.8
H12A—C12—H12B	107.6	H22A—C22—H22B	107.7
C115—N111—N112	106.2 (2)	C215—N211—N212	106.5 (4)
C115—N111—C116	119.4 (4)	C215—N211—C216	119.3 (6)
N112—N111—C116	114.8 (4)	N212—N211—C216	114.7 (6)
C113—N112—N111	109.5 (3)	C213—N212—N211	109.7 (3)
C113—N112—C131	126.0 (4)	C213—N212—C231	125.9 (6)
N111—N112—C131	118.1 (4)	N211—N212—C231	118.0 (6)
O113—C113—N112	124.5 (3)	O213—C213—N212	124.4 (5)
O113—C113—C114	130.7 (3)	O213—C213—C214	130.4 (5)
N112—C113—C114	104.8 (2)	N212—C213—C214	104.9 (3)
C115—C114—N11	127.0 (4)	C215—C214—N21	126.9 (6)
C115—C114—C113	108.9 (2)	C215—C214—C213	108.9 (3)
N11—C114—C113	124.1 (3)	N21—C214—C213	123.8 (5)
C114—C115—N111	109.8 (4)	C214—C215—N211	109.9 (3)
C114—C115—C117	129.5 (3)	C214—C215—C217	129.3 (6)
N111—C115—C117	120.7 (4)	N211—C215—C217	120.7 (5)
N111—C116—H11A	109.5	N211—C216—H21A	109.5
N111—C116—H11B	109.5	N211—C216—H21B	109.5
H11A—C116—H11B	109.5	H21A—C216—H21B	109.5
N111—C116—H11C	109.5	N211—C216—H21C	109.5
H11A—C116—H11C	109.5	H21A—C216—H21C	109.5
H11B—C116—H11C	109.5	H21B—C216—H21C	109.5
C115—C117—H11D	109.5	C215—C217—H21D	109.5
C115—C117—H11E	109.5	C215—C217—H21E	109.5
H11D—C117—H11E	109.5	H21D—C217—H21E	109.5
C115—C117—H11F	109.5	C215—C217—H21F	109.5
H11D—C117—H11F	109.5	H21D—C217—H21F	109.5
H11E—C117—H11F	109.5	H21E—C217—H21F	109.5
C122—C121—C126	116.8 (3)	C222—C221—C226	116.8 (4)
C122—C121—C12	120.3 (3)	C222—C221—C22	121.0 (5)
C126—C121—C12	122.9 (3)	C226—C221—C22	122.1 (5)
C121—C122—C123	122.3 (3)	C221—C222—C223	122.3 (5)
C121—C122—Cl12	121.9 (3)	C221—C222—H222	118.9
C123—C122—Cl12	115.7 (3)	C223—C222—H222	118.9
C124—C123—C122	117.6 (3)	C224—C223—C222	117.5 (5)
C124—C123—H123	121.2	C224—C223—H223	121.3
C122—C123—H123	121.2	C222—C223—H223	121.3
C125—C124—C123	121.3 (4)	C225—C224—C223	121.3 (5)
C125—C124—H124	119.4	C225—C224—H224	119.3
C123—C124—H124	119.4	C223—C224—H224	119.3
C124—C125—C126	120.2 (4)	C224—C225—C226	119.9 (6)
C124—C125—H125	119.9	C224—C225—H225	120.0
C126—C125—H125	119.9	C226—C225—H225	120.0
C125—C126—C121	121.7 (4)	C225—C226—C221	121.5 (5)
C125—C126—H126	119.2	C225—C226—Cl26	116.6 (6)
C121—C126—H126	119.2	C221—C226—Cl26	121.3 (5)
C136—C131—C132	120.6 (4)	C236—C231—C232	120.4 (6)
C136—C131—N112	119.1 (4)	C236—C231—N212	119.3 (5)
C132—C131—N112	120.2 (3)	C232—C231—N212	120.1 (5)
C133—C132—C131	119.2 (4)	C233—C232—C231	119.0 (6)
C133—C132—H132	120.4	C233—C232—H232	120.5
C131—C132—H132	120.4	C231—C232—H232	120.5
C134—C133—C132	120.8 (4)	C234—C233—C232	120.5 (5)
C134—C133—H133	119.6	C234—C233—H233	119.8
C132—C133—H133	119.6	C232—C233—H233	119.8
C133—C134—C135	119.4 (3)	C233—C234—C235	119.3 (5)
C133—C134—H134	120.3	C233—C234—H234	120.4
C135—C134—H134	120.3	C235—C234—H234	120.4
C134—C135—C136	121.6 (4)	C234—C235—C236	121.3 (6)
C134—C135—H135	119.2	C234—C235—H235	119.3
C136—C135—H135	119.2	C236—C235—H235	119.3
C131—C136—C135	118.2 (5)	C231—C236—C235	118.0 (7)
C131—C136—H136	120.9	C231—C236—H236	121.0
C135—C136—H136	120.9	C235—C236—H236	121.0

O11—C11—N11—C114	21 (3)	O21—C21—N21—C214	−39 (4)
C12—C11—N11—C114	−175.3 (8)	C22—C21—N21—C214	162.3 (13)
O11—C11—C12—C121	8 (3)	O21—C21—C22—C221	9 (4)
N11—C11—C12—C121	−154.8 (9)	N21—C21—C22—C221	167.1 (14)
C115—N111—N112—C113	−9 (2)	C215—N211—N212—C213	−3 (3)
C116—N111—N112—C113	−144 (2)	C216—N211—N212—C213	−137 (3)
C115—N111—N112—C131	−163 (2)	C215—N211—N212—C231	−157 (3)
C116—N111—N112—C131	62.8 (19)	C216—N211—N212—C231	69 (3)
N111—N112—C113—O113	−174.6 (13)	N211—N212—C213—O213	−171 (2)
C131—N112—C113—O113	−23.6 (15)	C231—N212—C213—O213	−20 (3)
N111—N112—C113—C114	7.2 (13)	N211—N212—C213—C214	3 (2)
C131—N112—C113—C114	158.2 (11)	C231—N212—C213—C214	153.7 (18)
C11—N11—C114—C115	−79 (3)	C21—N21—C214—C215	−44 (5)
C11—N11—C114—C113	102.8 (15)	C21—N21—C214—C213	128 (2)
O113—C113—C114—C115	180 (2)	O213—C213—C214—C215	172 (4)
N112—C113—C114—C115	−2 (2)	N212—C213—C214—C215	−1 (4)
O113—C113—C114—N11	−1 (2)	O213—C213—C214—N21	−1 (3)
N112—C113—C114—N11	176.6 (11)	N212—C213—C214—N21	−173.9 (18)
N11—C114—C115—N111	177.5 (16)	N21—C214—C215—N211	172 (3)
C113—C114—C115—N111	−4 (3)	C213—C214—C215—N211	−1 (5)
N11—C114—C115—C117	−1 (6)	N21—C214—C215—C217	−12 (9)
C113—C114—C115—C117	178 (4)	C213—C214—C215—C217	175 (6)
N112—N111—C115—C114	8 (3)	N212—N211—C215—C214	2 (5)
C116—N111—C115—C114	140 (3)	C216—N211—C215—C214	134 (5)
N112—N111—C115—C117	−174 (3)	N212—N211—C215—C217	−174 (5)
C116—N111—C115—C117	−42 (3)	C216—N211—C215—C217	−42 (5)
C11—C12—C121—C122	67.3 (7)	C21—C22—C221—C222	96.8 (11)
C11—C12—C121—C126	−115.0 (6)	C21—C22—C221—C226	−87.3 (11)
C126—C121—C122—C123	−0.4 (14)	C226—C221—C222—C223	−2 (2)
C12—C121—C122—C123	177.3 (10)	C22—C221—C222—C223	174.4 (17)
C126—C121—C122—Cl12	−179.5 (6)	C221—C222—C223—C224	−2 (4)
C12—C121—C122—Cl12	−1.7 (10)	C222—C223—C224—C225	−1 (6)
C121—C122—C123—C124	1 (3)	C223—C224—C225—C226	7 (7)
Cl12—C122—C123—C124	179.9 (19)	C224—C225—C226—C221	−11 (5)
C122—C123—C124—C125	1 (4)	C224—C225—C226—Cl26	178 (3)
C123—C124—C125—C126	−4 (4)	C222—C221—C226—C225	8 (3)
C124—C125—C126—C121	4 (3)	C22—C221—C226—C225	−168.2 (19)
C122—C121—C126—C125	−1.9 (15)	C222—C221—C226—Cl26	178.6 (11)
C12—C121—C126—C125	−179.6 (12)	C22—C221—C226—Cl26	2.6 (17)
C113—N112—C131—C136	56 (3)	C213—N212—C231—C236	56 (4)
N111—N112—C131—C136	−155 (2)	N211—N212—C231—C236	−155 (4)
C113—N112—C131—C132	−127.2 (19)	C213—N212—C231—C232	−118 (3)
N111—N112—C131—C132	22 (2)	N211—N212—C231—C232	31 (3)
C136—C131—C132—C133	−4 (3)	C236—C231—C232—C233	10 (5)
N112—C131—C132—C133	179.1 (13)	N212—C231—C232—C233	−176 (2)
C131—C132—C133—C134	4 (2)	C231—C232—C233—C234	−12 (4)
C132—C133—C134—C135	0 (3)	C232—C233—C234—C235	3 (5)
C133—C134—C135—C136	−4 (4)	C233—C234—C235—C236	9 (6)
C132—C131—C136—C135	1 (4)	C232—C231—C236—C235	1 (7)
N112—C131—C136—C135	177 (2)	N212—C231—C236—C235	−173 (4)
C134—C135—C136—C131	4 (5)	C234—C235—C236—C231	−10 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O113ⁱ	0.82 (7)	2.15 (8)	2.94 (2)	162 (6)
N11—H11···O213ⁱ	0.82 (7)	2.08 (8)	2.88 (2)	168 (6)
N21—H21···O113ⁱ	0.92 (10)	2.00 (10)	2.91 (2)	161 (7)
N21—H21···O213ⁱ	0.92 (10)	1.95 (10)	2.82 (3)	158 (7)
C134—H134···O11ⁱⁱ	0.93	2.57	3.46 (4)	159
C234—H234···O21ⁱⁱ	0.93	2.49	3.40 (7)	164
C225—H225···O213ⁱⁱⁱ	0.93	2.39	3.28 (2)	160

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

Selected torsion angles (°) for compounds (I)–(III) top

Parameter	(I)		(II)		(III)
	x = 1	x = 2	x = 1	x = 2	x = 1	x = 2
Cx13—Cx14—Nx1—Cx1
	122.2 (2)	129.1 (2)	102.8 (15)	128 (2)	121.0 (2)	136.5 (3)
Cx14—Nx1—Nx1—Cx2
	-174.36 (18)	177.29 (19)	-175.3 (8)	162.3 (13)	-170.6 (2)	172.7 (2)
Nx1—Cx1—Cx2—Cx21
	114.3 (2)	-89.3 (3)	-154.8 (9)	167.12 (14)	122.2 (2)	-88.9 (3)
Cx1—Cx2—Cx21—Cx22
	80.8 (3)	-82.5 (3)	67.3 (7)	96.8 (11)	-84.8 (3)	-84.7 (3)
Nx11—Nx12—Cx31—Cx32
	22.6 (3)	-43.9 (3)	22 (2)	31 (3)	26.7 (3)	-34.7 (3)

For compounds (I) and (III), the indices x (1 or 2) refer to the two independent molecules in the selected asymmetric units; for compound (II), these indices refer to the major and minor disorder components (cf. Figs. 1 and 2)

Hydrogen bonds parameters (Å, °) for compounds (I) and (II) top

	D—H···A	D—H	H···A	D···A	D—H···A
(I)	N11—H11···O213	0.87 (3)	1.93 (2)	2.781 (2)	169 (2)
	N21—H21···O113	0.84 (2)	2.01 (2)	2.845 (2)	178 (4)
	C133—H133···O11ⁱ	0.93	2.52	3.446 (3)	171
(II)	N11—H11···O113ⁱⁱ	0.82 (7)	2.15 (8)	2.94 (2)	162 (6)
	N11—H11···O213ⁱⁱ	0.82 (7)	2.08 (8)	2.88 (2)	168 (6)
	N21—H21···O113ⁱⁱ	0.92 (10)	2.00 (10)	2.91 (2)	161 (7)
	N21—H21···O213ⁱⁱ	0.92 (10)	1.95 (10)	2.82 (3)	158 (7)
	C134—H134···O11ⁱⁱⁱ	0.93	2.57	3.46 (4)	159
	C234—H234···O21ⁱⁱⁱ	0.93	2.49	3.40 (7)	164
	C225—H225···O213^iv	0.93	2.39	3.28 (2)	160

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

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Different mol­ecular conformations co-exist in each of three 2-aryl-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-yl)acetamides: hydrogen bonding in zero, one and two dimensions

Supporting information

Different molecular conformations co-exist in each of three 2-aryl-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamides: hydrogen bonding in zero, one and two dimensions