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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616012870/sk3634sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616012870/sk3634Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616012870/sk3634IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616012870/sk3634Isup4.cml
Supplementary material

cml

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
C19H18ClN3O2Z = 4
Mr = 355.81F(000) = 744
Triclinic, P1Dx = 1.347 Mg m3
a = 10.1018 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.6099 (5) ÅCell parameters from 8317 reflections
c = 18.8129 (11) Åθ = 1.1–28.2°
α = 100.292 (3)°µ = 0.24 mm1
β = 91.881 (3)°T = 295 K
γ = 116.873 (2)°Block, colourless
V = 1754.78 (15) Å30.30 × 0.20 × 0.20 mm
Data collection top
Bruker APEXII area-detector
diffractometer
7205 independent reflections
Radiation source: fine-focus sealed tube5041 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 26.6°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1212
Tmin = 0.788, Tmax = 0.954k = 1313
32307 measured reflectionsl = 2323
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.133 w = 1/[σ2(Fo2) + (0.0535P)2 + 0.8541P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
7205 reflectionsΔρmax = 0.58 e Å3
461 parametersΔρmin = 0.63 e Å3
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
xyzUiso*/Ueq
C110.0605 (2)0.4111 (2)0.35897 (11)0.0430 (5)
O110.02706 (17)0.35666 (18)0.40064 (9)0.0587 (4)
N110.19775 (19)0.41816 (17)0.36076 (9)0.0393 (4)
H110.255 (3)0.453 (2)0.3284 (12)0.047*
C120.0218 (3)0.4743 (2)0.30052 (14)0.0545 (6)
H12A0.00710.54660.32240.065*
H12B0.10850.52080.27600.065*
N1110.2896 (2)0.27333 (18)0.50227 (8)0.0426 (4)
N1120.33015 (19)0.20766 (17)0.44120 (8)0.0403 (4)
C1130.2960 (2)0.2495 (2)0.37988 (10)0.0370 (4)
O1130.30568 (19)0.19812 (16)0.31741 (7)0.0511 (4)
C1140.2477 (2)0.35432 (19)0.40692 (10)0.0366 (4)
C1150.2510 (2)0.3693 (2)0.48018 (11)0.0415 (5)
C1160.3858 (3)0.3110 (3)0.57066 (11)0.0549 (6)
H11A0.48360.38650.56820.082*
H11B0.39330.22730.57840.082*
H11C0.34350.34390.61030.082*
C1170.2218 (3)0.4710 (3)0.53415 (13)0.0609 (6)
H11D0.31500.54770.56000.091*
H11E0.16110.42020.56800.091*
H11F0.17030.51100.50940.091*
C1210.1055 (2)0.3547 (2)0.24629 (12)0.0478 (5)
C1220.2525 (3)0.3030 (3)0.26009 (13)0.0568 (6)
H1220.27460.34870.30150.068*
C1230.3667 (3)0.1853 (3)0.21375 (13)0.0623 (7)
H1230.46500.15140.22380.075*
C1240.3343 (3)0.1186 (3)0.15289 (13)0.0574 (6)
Cl140.47626 (10)0.03248 (9)0.09513 (4)0.0943 (3)
C1250.1915 (3)0.1699 (3)0.13668 (13)0.0636 (7)
H1250.17100.12550.09430.076*
C1260.0771 (3)0.2878 (3)0.18325 (14)0.0594 (6)
H1260.02040.32260.17200.071*
C1310.3196 (2)0.0688 (2)0.43913 (11)0.0399 (4)
C1320.2258 (3)0.0209 (2)0.48042 (12)0.0517 (5)
H1320.16880.00880.51010.062*
C1330.2177 (3)0.1559 (3)0.47704 (15)0.0657 (7)
H1330.15710.21620.50570.079*
C1340.2982 (3)0.2006 (3)0.43200 (16)0.0695 (7)
H1340.29110.29180.42940.083*
C1350.3892 (3)0.1120 (3)0.39061 (15)0.0683 (7)
H1350.44260.14390.35940.082*
C1360.4026 (3)0.0239 (3)0.39467 (13)0.0542 (6)
H1360.46730.08510.36760.065*
C210.1899 (2)0.1687 (2)0.12171 (13)0.0476 (5)
O210.1859 (2)0.19074 (18)0.06084 (9)0.0670 (5)
N210.2985 (2)0.26017 (18)0.17678 (10)0.0444 (4)
H210.299 (3)0.242 (3)0.2182 (13)0.053*
C220.0736 (3)0.0327 (2)0.14195 (15)0.0583 (6)
H22A0.06150.05490.19290.070*
H22B0.02180.00040.11310.070*
N2110.6348 (2)0.54849 (19)0.14139 (10)0.0515 (5)
N2120.59086 (19)0.62246 (18)0.19668 (9)0.0443 (4)
C2130.4620 (2)0.5246 (2)0.21926 (10)0.0391 (4)
O2130.40726 (17)0.55872 (16)0.27238 (8)0.0527 (4)
C2140.4214 (2)0.3899 (2)0.17045 (10)0.0391 (4)
C2150.5246 (2)0.4090 (2)0.12366 (11)0.0458 (5)
C2160.7181 (4)0.6308 (3)0.08971 (15)0.0876 (11)
H21A0.65400.65310.06130.131*
H21B0.75380.57460.05800.131*
H21C0.80160.71900.11560.131*
C2170.5321 (3)0.3049 (3)0.06221 (14)0.0651 (7)
H21D0.63300.31900.06280.098*
H21E0.50100.32000.01710.098*
H21F0.46710.20790.06680.098*
C2210.1166 (2)0.0881 (2)0.12951 (12)0.0450 (5)
C2220.0882 (2)0.1749 (2)0.06067 (12)0.0485 (5)
H2220.04520.15660.02190.058*
C2230.1228 (2)0.2881 (2)0.04885 (12)0.0492 (5)
H2230.10420.34520.00230.059*
C2240.1847 (3)0.3156 (2)0.10616 (12)0.0468 (5)
Cl240.22648 (8)0.45950 (7)0.09162 (4)0.0675 (2)
C2250.2144 (3)0.2317 (3)0.17520 (12)0.0540 (6)
H2250.25620.25150.21380.065*
C2260.1811 (3)0.1174 (2)0.18619 (12)0.0523 (6)
H2260.20240.05910.23260.063*
C2310.7044 (2)0.7494 (2)0.24460 (11)0.0444 (5)
C2320.8319 (3)0.7503 (3)0.27219 (13)0.0601 (6)
H2320.84750.66990.25870.072*
C2330.9370 (3)0.8729 (4)0.32045 (15)0.0794 (9)
H2331.02480.87560.33920.095*
C2340.9129 (3)0.9896 (3)0.34061 (15)0.0795 (10)
H2340.98341.07080.37390.095*
C2350.7866 (4)0.9887 (3)0.31254 (16)0.0749 (8)
H2350.77141.06930.32640.090*
C2360.6803 (3)0.8674 (2)0.26328 (13)0.0583 (6)
H2360.59420.86630.24330.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0410 (11)0.0343 (10)0.0495 (12)0.0144 (9)0.0053 (9)0.0084 (9)
O110.0444 (9)0.0690 (10)0.0657 (10)0.0240 (8)0.0183 (8)0.0263 (8)
N110.0394 (9)0.0358 (9)0.0434 (9)0.0155 (7)0.0108 (7)0.0151 (7)
C120.0465 (13)0.0462 (12)0.0732 (16)0.0207 (11)0.0031 (11)0.0221 (11)
N1110.0517 (10)0.0448 (9)0.0316 (8)0.0232 (8)0.0060 (7)0.0067 (7)
N1120.0505 (10)0.0397 (9)0.0339 (8)0.0230 (8)0.0086 (7)0.0096 (7)
C1130.0387 (10)0.0339 (10)0.0354 (10)0.0130 (8)0.0076 (8)0.0104 (8)
O1130.0757 (11)0.0528 (9)0.0352 (8)0.0376 (8)0.0142 (7)0.0118 (6)
C1140.0363 (10)0.0320 (9)0.0371 (10)0.0119 (8)0.0060 (8)0.0078 (8)
C1150.0443 (11)0.0365 (10)0.0384 (11)0.0152 (9)0.0066 (9)0.0050 (8)
C1160.0614 (14)0.0546 (13)0.0390 (11)0.0204 (12)0.0035 (10)0.0077 (10)
C1170.0813 (18)0.0579 (14)0.0473 (13)0.0388 (14)0.0115 (12)0.0020 (11)
C1210.0488 (12)0.0500 (12)0.0521 (13)0.0263 (11)0.0080 (10)0.0195 (10)
C1220.0519 (14)0.0696 (15)0.0480 (13)0.0304 (12)0.0094 (11)0.0044 (11)
C1230.0472 (13)0.0791 (17)0.0519 (14)0.0234 (13)0.0087 (11)0.0099 (12)
C1240.0618 (15)0.0602 (14)0.0460 (13)0.0248 (12)0.0046 (11)0.0124 (11)
Cl140.1013 (6)0.0752 (5)0.0688 (5)0.0169 (4)0.0090 (4)0.0033 (4)
C1250.0801 (18)0.0754 (17)0.0455 (13)0.0448 (15)0.0169 (13)0.0119 (12)
C1260.0518 (14)0.0755 (17)0.0633 (15)0.0341 (13)0.0235 (12)0.0294 (13)
C1310.0437 (11)0.0366 (10)0.0385 (10)0.0176 (9)0.0006 (8)0.0096 (8)
C1320.0524 (13)0.0483 (12)0.0517 (13)0.0192 (11)0.0081 (10)0.0161 (10)
C1330.0688 (17)0.0428 (13)0.0724 (17)0.0116 (12)0.0027 (13)0.0229 (12)
C1340.089 (2)0.0420 (13)0.0759 (18)0.0314 (14)0.0039 (15)0.0108 (13)
C1350.091 (2)0.0697 (17)0.0638 (16)0.0554 (16)0.0091 (14)0.0109 (13)
C1360.0644 (15)0.0563 (13)0.0541 (13)0.0356 (12)0.0143 (11)0.0192 (11)
C210.0433 (12)0.0365 (11)0.0562 (14)0.0136 (9)0.0022 (10)0.0088 (10)
O210.0644 (11)0.0591 (10)0.0564 (10)0.0123 (9)0.0152 (8)0.0126 (8)
N210.0484 (10)0.0349 (9)0.0395 (9)0.0092 (8)0.0036 (8)0.0117 (7)
C220.0435 (12)0.0376 (11)0.0855 (17)0.0127 (10)0.0146 (12)0.0092 (11)
N2110.0470 (10)0.0460 (10)0.0429 (10)0.0079 (8)0.0151 (8)0.0025 (8)
N2120.0386 (9)0.0396 (9)0.0375 (9)0.0049 (7)0.0092 (7)0.0033 (7)
C2130.0380 (11)0.0379 (10)0.0354 (10)0.0116 (9)0.0054 (8)0.0104 (8)
O2130.0491 (9)0.0472 (8)0.0456 (8)0.0094 (7)0.0168 (7)0.0055 (7)
C2140.0398 (11)0.0362 (10)0.0361 (10)0.0127 (9)0.0027 (8)0.0104 (8)
C2150.0469 (12)0.0441 (11)0.0394 (11)0.0168 (10)0.0038 (9)0.0050 (9)
C2160.086 (2)0.0715 (18)0.0609 (16)0.0004 (16)0.0385 (15)0.0074 (14)
C2170.0706 (17)0.0587 (15)0.0564 (15)0.0265 (13)0.0134 (12)0.0007 (12)
C2210.0347 (10)0.0320 (10)0.0564 (13)0.0050 (8)0.0115 (9)0.0096 (9)
C2220.0465 (12)0.0457 (12)0.0472 (12)0.0155 (10)0.0029 (9)0.0131 (10)
C2230.0520 (13)0.0463 (12)0.0408 (11)0.0178 (10)0.0053 (10)0.0037 (9)
C2240.0511 (13)0.0412 (11)0.0464 (12)0.0192 (10)0.0087 (10)0.0115 (9)
Cl240.0870 (5)0.0629 (4)0.0687 (4)0.0460 (4)0.0189 (3)0.0202 (3)
C2250.0606 (14)0.0558 (14)0.0426 (12)0.0232 (12)0.0056 (10)0.0148 (10)
C2260.0554 (13)0.0452 (12)0.0440 (12)0.0151 (11)0.0084 (10)0.0034 (9)
C2310.0395 (11)0.0389 (11)0.0371 (10)0.0030 (9)0.0103 (9)0.0079 (8)
C2320.0476 (14)0.0649 (15)0.0559 (14)0.0200 (12)0.0045 (11)0.0023 (12)
C2330.0410 (14)0.100 (2)0.0605 (16)0.0094 (15)0.0014 (12)0.0040 (16)
C2340.0570 (17)0.0640 (18)0.0588 (16)0.0143 (14)0.0115 (13)0.0083 (13)
C2350.087 (2)0.0383 (13)0.0740 (18)0.0097 (14)0.0189 (16)0.0042 (12)
C2360.0616 (15)0.0444 (13)0.0578 (14)0.0148 (11)0.0101 (11)0.0122 (11)
Geometric parameters (Å, º) top
C11—O111.215 (2)C21—O211.212 (3)
C11—N111.353 (3)C21—N211.350 (3)
C11—C121.511 (3)C21—C221.517 (3)
N11—C1141.399 (3)N21—C2141.405 (2)
N11—H110.87 (2)N21—H210.83 (2)
C12—C1211.510 (3)C22—C2211.512 (3)
C12—H12A0.9700C22—H22A0.9700
C12—H12B0.9700C22—H22B0.9700
N111—C1151.364 (3)N211—C2151.360 (3)
N111—N1121.406 (2)N211—N2121.396 (2)
N111—C1161.463 (3)N211—C2161.452 (3)
N112—C1131.394 (2)N212—C2131.387 (2)
N112—C1311.422 (3)N212—C2311.430 (2)
C113—O1131.231 (2)C213—O2131.235 (2)
C113—C1141.428 (3)C213—C2141.425 (3)
C114—C1151.356 (3)C214—C2151.355 (3)
C115—C1171.483 (3)C215—C2171.479 (3)
C116—H11A0.9600C216—H21A0.9600
C116—H11B0.9600C216—H21B0.9600
C116—H11C0.9600C216—H21C0.9600
C117—H11D0.9600C217—H21D0.9600
C117—H11E0.9600C217—H21E0.9600
C117—H11F0.9600C217—H21F0.9600
C121—C1261.378 (3)C221—C2261.383 (3)
C121—C1221.383 (3)C221—C2221.385 (3)
C122—C1231.376 (3)C222—C2231.380 (3)
C122—H1220.9300C222—H2220.9300
C123—C1241.365 (3)C223—C2241.368 (3)
C123—H1230.9300C223—H2230.9300
C124—C1251.360 (4)C224—C2251.374 (3)
C124—Cl141.733 (3)C224—Cl241.740 (2)
C125—C1261.380 (4)C225—C2261.382 (3)
C125—H1250.9300C225—H2250.9300
C126—H1260.9300C226—H2260.9300
C131—C1361.376 (3)C231—C2321.368 (3)
C131—C1321.380 (3)C231—C2361.369 (3)
C132—C1331.387 (3)C232—C2331.382 (4)
C132—H1320.9300C232—H2320.9300
C133—C1341.361 (4)C233—C2341.359 (5)
C133—H1330.9300C233—H2330.9300
C134—C1351.365 (4)C234—C2351.361 (5)
C134—H1340.9300C234—H2340.9300
C135—C1361.373 (3)C235—C2361.388 (4)
C135—H1350.9300C235—H2350.9300
C136—H1360.9300C236—H2360.9300
O11—C11—N11122.9 (2)O21—C21—N21123.5 (2)
O11—C11—C12121.8 (2)O21—C21—C22122.3 (2)
N11—C11—C12115.31 (18)N21—C21—C22114.1 (2)
C11—N11—C114123.23 (17)C21—N21—C214124.54 (18)
C11—N11—H11120.1 (15)C21—N21—H21121.6 (16)
C114—N11—H11116.2 (15)C214—N21—H21113.9 (16)
C121—C12—C11109.27 (17)C221—C22—C21112.18 (18)
C121—C12—H12A109.8C221—C22—H22A109.2
C11—C12—H12A109.8C21—C22—H22A109.2
C121—C12—H12B109.8C221—C22—H22B109.2
C11—C12—H12B109.8C21—C22—H22B109.2
H12A—C12—H12B108.3H22A—C22—H22B107.9
C115—N111—N112106.81 (15)C215—N211—N212107.21 (16)
C115—N111—C116121.99 (17)C215—N211—C216125.02 (19)
N112—N111—C116114.89 (18)N212—N211—C216116.1 (2)
C113—N112—N111108.88 (16)C213—N212—N211109.36 (15)
C113—N112—C131123.24 (16)C213—N212—C231123.33 (16)
N111—N112—C131118.59 (15)N211—N212—C231118.30 (16)
O113—C113—N112123.48 (18)O213—C213—N212122.90 (18)
O113—C113—C114131.26 (18)O213—C213—C214132.45 (18)
N112—C113—C114105.24 (16)N212—C213—C214104.62 (17)
C115—C114—N11129.18 (19)C215—C214—N21128.16 (19)
C115—C114—C113108.43 (18)C215—C214—C213109.06 (17)
N11—C114—C113122.26 (17)N21—C214—C213122.61 (18)
C114—C115—N111110.00 (17)C214—C215—N211109.27 (18)
C114—C115—C117129.6 (2)C214—C215—C217130.3 (2)
N111—C115—C117120.36 (19)N211—C215—C217120.4 (2)
N111—C116—H11A109.5N211—C216—H21A109.5
N111—C116—H11B109.5N211—C216—H21B109.5
H11A—C116—H11B109.5H21A—C216—H21B109.5
N111—C116—H11C109.5N211—C216—H21C109.5
H11A—C116—H11C109.5H21A—C216—H21C109.5
H11B—C116—H11C109.5H21B—C216—H21C109.5
C115—C117—H11D109.5C215—C217—H21D109.5
C115—C117—H11E109.5C215—C217—H21E109.5
H11D—C117—H11E109.5H21D—C217—H21E109.5
C115—C117—H11F109.5C215—C217—H21F109.5
H11D—C117—H11F109.5H21D—C217—H21F109.5
H11E—C117—H11F109.5H21E—C217—H21F109.5
C126—C121—C122118.0 (2)C226—C221—C222118.4 (2)
C126—C121—C12120.4 (2)C226—C221—C22121.4 (2)
C122—C121—C12121.5 (2)C222—C221—C22120.2 (2)
C123—C122—C121121.3 (2)C223—C222—C221120.9 (2)
C123—C122—H122119.4C223—C222—H222119.5
C121—C122—H122119.4C221—C222—H222119.5
C124—C123—C122119.3 (2)C224—C223—C222119.4 (2)
C124—C123—H123120.3C224—C223—H223120.3
C122—C123—H123120.3C222—C223—H223120.3
C125—C124—C123120.7 (2)C223—C224—C225121.3 (2)
C125—C124—Cl14119.4 (2)C223—C224—Cl24119.50 (17)
C123—C124—Cl14119.9 (2)C225—C224—Cl24119.24 (18)
C124—C125—C126119.9 (2)C224—C225—C226118.8 (2)
C124—C125—H125120.1C224—C225—H225120.6
C126—C125—H125120.1C226—C225—H225120.6
C121—C126—C125120.8 (2)C225—C226—C221121.3 (2)
C121—C126—H126119.6C225—C226—H226119.4
C125—C126—H126119.6C221—C226—H226119.4
C136—C131—C132120.3 (2)C232—C231—C236121.3 (2)
C136—C131—N112119.24 (18)C232—C231—N212120.3 (2)
C132—C131—N112120.46 (19)C236—C231—N212118.4 (2)
C131—C132—C133119.1 (2)C231—C232—C233118.8 (3)
C131—C132—H132120.5C231—C232—H232120.6
C133—C132—H132120.5C233—C232—H232120.6
C134—C133—C132120.3 (2)C234—C233—C232120.4 (3)
C134—C133—H133119.9C234—C233—H233119.8
C132—C133—H133119.9C232—C233—H233119.8
C133—C134—C135120.3 (2)C233—C234—C235120.6 (2)
C133—C134—H134119.9C233—C234—H234119.7
C135—C134—H134119.9C235—C234—H234119.7
C134—C135—C136120.5 (3)C234—C235—C236120.0 (3)
C134—C135—H135119.7C234—C235—H235120.0
C136—C135—H135119.7C236—C235—H235120.0
C135—C136—C131119.5 (2)C231—C236—C235118.8 (3)
C135—C136—H136120.2C231—C236—H236120.6
C131—C136—H136120.2C235—C236—H236120.6
O11—C11—N11—C1144.9 (3)O21—C21—N21—C2141.4 (4)
C12—C11—N11—C114174.36 (18)C22—C21—N21—C214177.29 (19)
O11—C11—C12—C12165.0 (3)O21—C21—C22—C22189.4 (3)
N11—C11—C12—C121114.3 (2)N21—C21—C22—C22189.3 (3)
C115—N111—N112—C1138.2 (2)C215—N211—N212—C2137.2 (2)
C116—N111—N112—C113146.82 (17)C216—N211—N212—C213152.4 (2)
C115—N111—N112—C131155.98 (17)C215—N211—N212—C231155.52 (19)
C116—N111—N112—C13165.4 (2)C216—N211—N212—C23159.3 (3)
N111—N112—C113—O113172.76 (18)N211—N212—C213—O213172.7 (2)
C131—N112—C113—O11326.8 (3)C231—N212—C213—O21326.3 (3)
N111—N112—C113—C1145.8 (2)N211—N212—C213—C2145.5 (2)
C131—N112—C113—C114151.75 (18)C231—N212—C213—C214151.9 (2)
C11—N11—C114—C11553.2 (3)C21—N21—C214—C21556.2 (3)
C11—N11—C114—C113122.2 (2)C21—N21—C214—C213129.1 (2)
O113—C113—C114—C115177.1 (2)O213—C213—C214—C215176.1 (2)
N112—C113—C114—C1151.3 (2)N212—C213—C214—C2151.8 (2)
O113—C113—C114—N110.9 (3)O213—C213—C214—N210.5 (4)
N112—C113—C114—N11177.47 (16)N212—C213—C214—N21177.38 (18)
N11—C114—C115—N111171.97 (18)N21—C214—C215—N211172.6 (2)
C113—C114—C115—N1113.9 (2)C213—C214—C215—N2112.6 (3)
N11—C114—C115—C1178.9 (4)N21—C214—C215—C2176.2 (4)
C113—C114—C115—C117175.3 (2)C213—C214—C215—C217178.5 (2)
N112—N111—C115—C1147.4 (2)N212—N211—C215—C2146.0 (2)
C116—N111—C115—C114142.4 (2)C216—N211—C215—C214147.2 (3)
N112—N111—C115—C117171.84 (19)N212—N211—C215—C217175.0 (2)
C116—N111—C115—C11736.8 (3)C216—N211—C215—C21733.8 (4)
C11—C12—C121—C12695.2 (3)C21—C22—C221—C22699.2 (3)
C11—C12—C121—C12280.8 (3)C21—C22—C221—C22282.5 (3)
C126—C121—C122—C1232.2 (4)C226—C221—C222—C2230.2 (3)
C12—C121—C122—C123173.9 (2)C22—C221—C222—C223178.14 (19)
C121—C122—C123—C1240.2 (4)C221—C222—C223—C2240.6 (3)
C122—C123—C124—C1251.9 (4)C222—C223—C224—C2250.6 (3)
C122—C123—C124—Cl14178.4 (2)C222—C223—C224—Cl24179.27 (17)
C123—C124—C125—C1262.0 (4)C223—C224—C225—C2260.2 (3)
Cl14—C124—C125—C126178.3 (2)Cl24—C224—C225—C226179.87 (17)
C122—C121—C126—C1252.1 (4)C224—C225—C226—C2211.1 (3)
C12—C121—C126—C125174.0 (2)C222—C221—C226—C2251.1 (3)
C124—C125—C126—C1210.0 (4)C22—C221—C226—C225177.2 (2)
C113—N112—C131—C13658.8 (3)C213—N212—C231—C23299.7 (3)
N111—N112—C131—C136158.29 (19)N211—N212—C231—C23243.9 (3)
C113—N112—C131—C132120.3 (2)C213—N212—C231—C23678.7 (3)
N111—N112—C131—C13222.6 (3)N211—N212—C231—C236137.7 (2)
C136—C131—C132—C1330.7 (3)C236—C231—C232—C2330.7 (3)
N112—C131—C132—C133179.8 (2)N212—C231—C232—C233177.7 (2)
C131—C132—C133—C1341.8 (4)C231—C232—C233—C2340.7 (4)
C132—C133—C134—C1351.0 (4)C232—C233—C234—C2351.3 (4)
C133—C134—C135—C1361.0 (4)C233—C234—C235—C2360.5 (4)
C134—C135—C136—C1312.1 (4)C232—C231—C236—C2351.5 (3)
C132—C131—C136—C1351.2 (3)N212—C231—C236—C235176.9 (2)
N112—C131—C136—C135177.9 (2)C234—C235—C236—C2310.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O2130.87 (3)1.93 (2)2.781 (2)169 (2)
N21—H21···O1130.84 (2)2.01 (2)2.845 (2)178 (4)
C133—H133···O11i0.932.523.446 (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
C19H18ClN3O2F(000) = 1488
Mr = 355.81Dx = 1.336 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 23.023 (3) ÅCell parameters from 6192 reflections
b = 8.2976 (10) Åθ = 2.1–32.2°
c = 21.602 (3) ŵ = 0.23 mm1
β = 120.957 (14)°T = 295 K
V = 3538.9 (9) Å3Block, colourless
Z = 80.40 × 0.30 × 0.20 mm
Data collection top
Bruker APEXII area-detector
diffractometer
4079 independent reflections
Radiation source: fine-focus sealed tube3038 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 27.6°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2929
Tmin = 0.767, Tmax = 0.954k = 810
33715 measured reflectionsl = 2828
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.051 w = 1/[σ2(Fo2) + (0.0639P)2 + 3.3163P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.149(Δ/σ)max = 0.007
S = 1.03Δρmax = 0.30 e Å3
4079 reflectionsΔρmin = 0.41 e Å3
319 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
64 restraintsExtinction coefficient: 0.0042 (5)
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
xyzUiso*/UeqOcc. (<1)
C110.5797 (2)0.6114 (5)0.3652 (2)0.0430 (10)0.6020 (18)
O110.6397 (10)0.563 (3)0.404 (2)0.093 (3)0.6020 (18)
N110.5674 (5)0.7661 (13)0.3420 (9)0.0447 (8)0.6020 (18)
H110.532 (3)0.811 (7)0.332 (3)0.054*0.6020 (18)
C120.51822 (15)0.5266 (4)0.3591 (2)0.0521 (7)0.6020 (18)
H12A0.49170.60490.36750.063*0.6020 (18)
H12B0.49020.48620.31030.063*0.6020 (18)
N1110.7060 (7)1.016 (3)0.3680 (6)0.0452 (7)0.6020 (18)
N1120.6676 (5)1.0041 (18)0.2923 (6)0.0418 (9)0.6020 (18)
C1130.6138 (4)0.8990 (11)0.2722 (5)0.0327 (15)0.6020 (18)
O1130.5739 (5)0.8552 (12)0.2095 (5)0.0432 (15)0.6020 (18)
C1140.6156 (6)0.8630 (13)0.3379 (5)0.0365 (13)0.6020 (18)
C1150.6693 (13)0.939 (5)0.3931 (5)0.0435 (6)0.6020 (18)
C1160.734 (2)1.177 (4)0.3956 (12)0.0678 (8)0.6020 (18)
H11A0.76511.17110.44670.102*0.6020 (18)
H11B0.69741.24920.38630.102*0.6020 (18)
H11C0.75661.21610.37200.102*0.6020 (18)
C1170.6917 (11)0.943 (3)0.4710 (5)0.0647 (10)0.6020 (18)
H11D0.66300.87470.47970.097*0.6020 (18)
H11E0.68891.05170.48480.097*0.6020 (18)
H11F0.73770.90620.49900.097*0.6020 (18)
C1210.5354 (3)0.3900 (4)0.41070 (17)0.0420 (10)0.6020 (18)
C1220.5669 (4)0.4185 (6)0.4834 (2)0.0549 (11)0.6020 (18)
C1230.5817 (8)0.2935 (9)0.5341 (3)0.0690 (13)0.6020 (18)
H1230.60270.31510.58320.083*0.6020 (18)
C1240.5641 (15)0.1393 (9)0.5081 (4)0.0723 (14)0.6020 (18)
H1240.57230.05530.54010.087*0.6020 (18)
C1250.5348 (10)0.1072 (6)0.4367 (4)0.0722 (13)0.6020 (18)
H1250.52560.00110.42050.087*0.6020 (18)
C1260.5187 (4)0.2301 (5)0.3883 (3)0.0604 (11)0.6020 (18)
H1260.49610.20660.33920.073*0.6020 (18)
C1310.7008 (5)1.034 (3)0.2530 (7)0.0450 (5)0.6020 (18)
C1320.7707 (5)1.0201 (12)0.2868 (6)0.0567 (18)0.6020 (18)
H1320.79630.99300.33550.068*0.6020 (18)
C1330.8017 (6)1.047 (2)0.2473 (9)0.077 (3)0.6020 (18)
H1330.84811.03100.26880.092*0.6020 (18)
C1340.7653 (8)1.0974 (18)0.1777 (8)0.076 (2)0.6020 (18)
H1340.78661.11590.15160.091*0.6020 (18)
C1350.6974 (9)1.120 (4)0.1464 (7)0.075 (3)0.6020 (18)
H1350.67301.16080.09970.091*0.6020 (18)
C1360.6634 (8)1.084 (4)0.1829 (8)0.0616 (14)0.6020 (18)
H1360.61661.09470.16010.074*0.6020 (18)
Cl120.59006 (6)0.6106 (2)0.51896 (6)0.0847 (4)0.6020 (18)
C210.5859 (3)0.6482 (9)0.3872 (4)0.0430 (10)0.3980 (18)
O210.6348 (15)0.564 (4)0.395 (4)0.093 (3)0.3980 (18)
N210.5662 (7)0.779 (2)0.3433 (13)0.0447 (8)0.3980 (18)
H210.520 (4)0.793 (11)0.317 (4)0.054*0.3980 (18)
C220.5300 (2)0.5857 (6)0.3992 (3)0.0521 (7)0.3980 (18)
H22A0.52400.66130.42970.063*0.3980 (18)
H22B0.48780.58170.35310.063*0.3980 (18)
N2110.7063 (11)1.023 (4)0.3698 (9)0.0452 (7)0.3980 (18)
N2120.6664 (8)1.018 (3)0.2941 (8)0.0418 (9)0.3980 (18)
C2130.6083 (7)0.928 (2)0.2732 (7)0.0327 (15)0.3980 (18)
O2130.5674 (8)0.887 (2)0.2103 (8)0.0432 (15)0.3980 (18)
C2140.6123 (10)0.884 (2)0.3393 (8)0.0365 (13)0.3980 (18)
C2150.6706 (19)0.943 (7)0.3952 (8)0.0435 (6)0.3980 (18)
C2160.736 (3)1.181 (6)0.3999 (18)0.0678 (8)0.3980 (18)
H21A0.75611.22480.37450.102*0.3980 (18)
H21B0.76941.16990.45010.102*0.3980 (18)
H21C0.70061.25260.39490.102*0.3980 (18)
C2170.6953 (16)0.939 (5)0.4738 (8)0.0647 (10)0.3980 (18)
H21D0.67401.02360.48530.097*0.3980 (18)
H21E0.74350.95410.50070.097*0.3980 (18)
H21F0.68440.83670.48610.097*0.3980 (18)
C2210.5440 (5)0.4227 (7)0.4331 (4)0.0420 (10)0.3980 (18)
C2220.5713 (7)0.4054 (11)0.5057 (4)0.0549 (11)0.3980 (18)
H2220.58480.49700.53460.066*0.3980 (18)
C2230.5797 (14)0.2525 (14)0.5387 (5)0.0690 (13)0.3980 (18)
H2230.59950.24240.58840.083*0.3980 (18)
C2240.558 (2)0.1199 (13)0.4944 (7)0.0723 (14)0.3980 (18)
H2240.56290.01800.51460.087*0.3980 (18)
C2250.5279 (16)0.1345 (10)0.4219 (7)0.0722 (13)0.3980 (18)
H2250.50890.04480.39230.087*0.3980 (18)
C2260.5260 (8)0.2811 (9)0.3921 (4)0.0604 (11)0.3980 (18)
C2310.6996 (7)1.036 (5)0.2540 (10)0.0450 (5)0.3980 (18)
C2320.7656 (8)0.982 (2)0.2826 (10)0.0567 (18)0.3980 (18)
H2320.78760.92740.32650.068*0.3980 (18)
C2330.7983 (10)1.010 (4)0.2448 (14)0.077 (3)0.3980 (18)
H2330.84470.99310.26710.092*0.3980 (18)
C2340.7630 (13)1.062 (3)0.1754 (13)0.076 (2)0.3980 (18)
H2340.78461.07690.14940.091*0.3980 (18)
C2350.6956 (13)1.093 (6)0.1443 (11)0.075 (3)0.3980 (18)
H2350.67021.11530.09510.091*0.3980 (18)
C2360.6638 (11)1.093 (7)0.1849 (12)0.0616 (14)0.3980 (18)
H2360.61971.13060.16540.074*0.3980 (18)
Cl260.4895 (2)0.2868 (4)0.2999 (2)0.1328 (11)0.3980 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0348 (12)0.049 (2)0.050 (3)0.0007 (12)0.0253 (18)0.0039 (16)
O110.043 (2)0.0891 (13)0.151 (9)0.0239 (15)0.053 (5)0.066 (2)
N110.0298 (7)0.0521 (17)0.0548 (10)0.0040 (8)0.0236 (7)0.0137 (14)
C120.0339 (12)0.060 (2)0.0599 (19)0.0029 (12)0.0222 (15)0.0149 (14)
N1110.0397 (7)0.0557 (18)0.0398 (9)0.0131 (8)0.0201 (7)0.0099 (8)
N1120.0371 (7)0.051 (2)0.0396 (9)0.0126 (10)0.0211 (6)0.0059 (10)
C1130.0284 (15)0.029 (4)0.0435 (9)0.003 (2)0.0202 (9)0.0015 (16)
O1130.0343 (18)0.052 (4)0.0404 (7)0.007 (2)0.0170 (9)0.0066 (18)
C1140.0312 (12)0.038 (3)0.0442 (9)0.0035 (18)0.0222 (8)0.0033 (13)
C1150.0362 (11)0.0553 (19)0.0418 (10)0.0001 (8)0.0221 (10)0.0007 (12)
C1160.066 (2)0.070 (2)0.067 (3)0.0303 (13)0.033 (3)0.0273 (16)
C1170.050 (2)0.1021 (19)0.0416 (12)0.003 (2)0.0234 (13)0.0033 (14)
C1210.0298 (16)0.051 (2)0.042 (2)0.0077 (15)0.017 (2)0.0010 (18)
C1220.0437 (16)0.0665 (17)0.054 (3)0.0084 (13)0.025 (3)0.004 (2)
C1230.0453 (15)0.098 (4)0.0595 (15)0.005 (4)0.0238 (14)0.0260 (19)
C1240.051 (5)0.068 (2)0.086 (3)0.000 (3)0.027 (6)0.029 (2)
C1250.069 (4)0.047 (2)0.092 (4)0.009 (4)0.036 (5)0.014 (2)
C1260.053 (2)0.066 (3)0.0685 (16)0.011 (3)0.0349 (15)0.004 (2)
C1310.0470 (9)0.0461 (11)0.0512 (10)0.0155 (8)0.0320 (8)0.0093 (8)
C1320.0483 (17)0.055 (5)0.0749 (18)0.014 (3)0.0372 (15)0.005 (3)
C1330.0643 (18)0.082 (9)0.111 (2)0.022 (3)0.0634 (19)0.019 (4)
C1340.105 (2)0.066 (7)0.102 (2)0.050 (4)0.086 (2)0.041 (3)
C1350.101 (2)0.087 (9)0.0580 (14)0.037 (3)0.0546 (15)0.018 (3)
C1360.0594 (12)0.083 (4)0.0477 (12)0.0184 (13)0.0316 (10)0.0078 (18)
Cl120.0808 (7)0.0924 (8)0.0814 (7)0.0292 (6)0.0420 (6)0.0263 (6)
C210.0348 (12)0.049 (2)0.050 (3)0.0007 (12)0.0253 (18)0.0039 (16)
O210.043 (2)0.0891 (13)0.151 (9)0.0239 (15)0.053 (5)0.066 (2)
N210.0298 (7)0.0521 (17)0.0548 (10)0.0040 (8)0.0236 (7)0.0137 (14)
C220.0339 (12)0.060 (2)0.0599 (19)0.0029 (12)0.0222 (15)0.0149 (14)
N2110.0397 (7)0.0557 (18)0.0398 (9)0.0131 (8)0.0201 (7)0.0099 (8)
N2120.0371 (7)0.051 (2)0.0396 (9)0.0126 (10)0.0211 (6)0.0059 (10)
C2130.0284 (15)0.029 (4)0.0435 (9)0.003 (2)0.0202 (9)0.0015 (16)
O2130.0343 (18)0.052 (4)0.0404 (7)0.007 (2)0.0170 (9)0.0066 (18)
C2140.0312 (12)0.038 (3)0.0442 (9)0.0035 (18)0.0222 (8)0.0033 (13)
C2150.0362 (11)0.0553 (19)0.0418 (10)0.0001 (8)0.0221 (10)0.0007 (12)
C2160.066 (2)0.070 (2)0.067 (3)0.0303 (13)0.033 (3)0.0273 (16)
C2170.050 (2)0.1021 (19)0.0416 (12)0.003 (2)0.0234 (13)0.0033 (14)
C2210.0298 (16)0.051 (2)0.042 (2)0.0077 (15)0.017 (2)0.0010 (18)
C2220.0437 (16)0.0665 (17)0.054 (3)0.0084 (13)0.025 (3)0.004 (2)
C2230.0453 (15)0.098 (4)0.0595 (15)0.005 (4)0.0238 (14)0.0260 (19)
C2240.051 (5)0.068 (2)0.086 (3)0.000 (3)0.027 (6)0.029 (2)
C2250.069 (4)0.047 (2)0.092 (4)0.009 (4)0.036 (5)0.014 (2)
C2260.053 (2)0.066 (3)0.0685 (16)0.011 (3)0.0349 (15)0.004 (2)
C2310.0470 (9)0.0461 (11)0.0512 (10)0.0155 (8)0.0320 (8)0.0093 (8)
C2320.0483 (17)0.055 (5)0.0749 (18)0.014 (3)0.0372 (15)0.005 (3)
C2330.0643 (18)0.082 (9)0.111 (2)0.022 (3)0.0634 (19)0.019 (4)
C2340.105 (2)0.066 (7)0.102 (2)0.050 (4)0.086 (2)0.041 (3)
C2350.101 (2)0.087 (9)0.0580 (14)0.037 (3)0.0546 (15)0.018 (3)
C2360.0594 (12)0.083 (4)0.0477 (12)0.0184 (13)0.0316 (10)0.0078 (18)
Cl260.150 (2)0.183 (3)0.0636 (11)0.0293 (19)0.0536 (13)0.0027 (13)
Geometric parameters (Å, º) top
C11—O111.257 (15)C21—O211.258 (16)
C11—N111.353 (5)C21—N211.355 (5)
C11—C121.524 (3)C21—C221.528 (4)
N11—C1141.410 (3)N21—C2141.410 (3)
N11—H110.82 (7)N21—H210.91 (8)
C12—C1211.493 (3)C22—C2211.492 (4)
C12—H12A0.9700C22—H22A0.9700
C12—H12B0.9700C22—H22B0.9700
N111—C1151.373 (3)N211—C2151.373 (4)
N111—N1121.407 (3)N211—N2121.406 (4)
N111—C1161.467 (3)N211—C2161.467 (4)
N112—C1131.389 (3)N212—C2131.389 (4)
N112—C1311.427 (3)N212—C2311.427 (4)
C113—O1131.237 (3)C213—O2131.237 (3)
C113—C1141.430 (3)C213—C2141.430 (4)
C114—C1151.353 (5)C214—C2151.353 (5)
C115—C1171.487 (4)C215—C2171.487 (4)
C116—H11A0.9600C216—H21A0.9600
C116—H11B0.9600C216—H21B0.9600
C116—H11C0.9600C216—H21C0.9600
C117—H11D0.9600C217—H21D0.9600
C117—H11E0.9600C217—H21E0.9600
C117—H11F0.9600C217—H21F0.9600
C121—C1221.370 (4)C221—C2221.365 (5)
C121—C1261.397 (4)C221—C2261.399 (5)
C122—C1231.417 (4)C222—C2231.418 (5)
C122—Cl121.730 (5)C222—H2220.9300
C123—C1241.372 (5)C223—C2241.372 (5)
C123—H1230.9300C223—H2230.9300
C124—C1251.354 (5)C224—C2251.355 (5)
C124—H1240.9300C224—H2240.9300
C125—C1261.368 (5)C225—C2261.366 (5)
C125—H1250.9300C225—H2250.9300
C126—H1260.9300C226—Cl261.719 (7)
C131—C1361.366 (4)C231—C2361.366 (4)
C131—C1321.388 (5)C231—C2321.388 (6)
C132—C1331.385 (4)C232—C2331.386 (5)
C132—H1320.9300C232—H2320.9300
C133—C1341.356 (5)C233—C2341.357 (5)
C133—H1330.9300C233—H2330.9300
C134—C1351.360 (5)C234—C2351.360 (5)
C134—H1340.9300C234—H2340.9300
C135—C1361.401 (7)C235—C2361.402 (8)
C135—H1350.9300C235—H2350.9300
C136—H1360.9300C236—H2360.9300
O11—C11—N11119.8 (9)O21—C21—N21119.6 (12)
O11—C11—C12124.4 (4)O21—C21—C22124.0 (6)
N11—C11—C12113.4 (3)N21—C21—C22112.5 (4)
C11—N11—C114122.9 (5)C21—N21—C214123.1 (6)
C11—N11—H11121 (4)C21—N21—H21114 (6)
C114—N11—H11116 (4)C214—N21—H21123 (6)
C121—C12—C11114.1 (3)C221—C22—C21113.8 (4)
C121—C12—H12A108.7C221—C22—H22A108.8
C11—C12—H12A108.7C21—C22—H22A108.8
C121—C12—H12B108.7C221—C22—H22B108.8
C11—C12—H12B108.7C21—C22—H22B108.8
H12A—C12—H12B107.6H22A—C22—H22B107.7
C115—N111—N112106.2 (2)C215—N211—N212106.5 (4)
C115—N111—C116119.4 (4)C215—N211—C216119.3 (6)
N112—N111—C116114.8 (4)N212—N211—C216114.7 (6)
C113—N112—N111109.5 (3)C213—N212—N211109.7 (3)
C113—N112—C131126.0 (4)C213—N212—C231125.9 (6)
N111—N112—C131118.1 (4)N211—N212—C231118.0 (6)
O113—C113—N112124.5 (3)O213—C213—N212124.4 (5)
O113—C113—C114130.7 (3)O213—C213—C214130.4 (5)
N112—C113—C114104.8 (2)N212—C213—C214104.9 (3)
C115—C114—N11127.0 (4)C215—C214—N21126.9 (6)
C115—C114—C113108.9 (2)C215—C214—C213108.9 (3)
N11—C114—C113124.1 (3)N21—C214—C213123.8 (5)
C114—C115—N111109.8 (4)C214—C215—N211109.9 (3)
C114—C115—C117129.5 (3)C214—C215—C217129.3 (6)
N111—C115—C117120.7 (4)N211—C215—C217120.7 (5)
N111—C116—H11A109.5N211—C216—H21A109.5
N111—C116—H11B109.5N211—C216—H21B109.5
H11A—C116—H11B109.5H21A—C216—H21B109.5
N111—C116—H11C109.5N211—C216—H21C109.5
H11A—C116—H11C109.5H21A—C216—H21C109.5
H11B—C116—H11C109.5H21B—C216—H21C109.5
C115—C117—H11D109.5C215—C217—H21D109.5
C115—C117—H11E109.5C215—C217—H21E109.5
H11D—C117—H11E109.5H21D—C217—H21E109.5
C115—C117—H11F109.5C215—C217—H21F109.5
H11D—C117—H11F109.5H21D—C217—H21F109.5
H11E—C117—H11F109.5H21E—C217—H21F109.5
C122—C121—C126116.8 (3)C222—C221—C226116.8 (4)
C122—C121—C12120.3 (3)C222—C221—C22121.0 (5)
C126—C121—C12122.9 (3)C226—C221—C22122.1 (5)
C121—C122—C123122.3 (3)C221—C222—C223122.3 (5)
C121—C122—Cl12121.9 (3)C221—C222—H222118.9
C123—C122—Cl12115.7 (3)C223—C222—H222118.9
C124—C123—C122117.6 (3)C224—C223—C222117.5 (5)
C124—C123—H123121.2C224—C223—H223121.3
C122—C123—H123121.2C222—C223—H223121.3
C125—C124—C123121.3 (4)C225—C224—C223121.3 (5)
C125—C124—H124119.4C225—C224—H224119.3
C123—C124—H124119.4C223—C224—H224119.3
C124—C125—C126120.2 (4)C224—C225—C226119.9 (6)
C124—C125—H125119.9C224—C225—H225120.0
C126—C125—H125119.9C226—C225—H225120.0
C125—C126—C121121.7 (4)C225—C226—C221121.5 (5)
C125—C126—H126119.2C225—C226—Cl26116.6 (6)
C121—C126—H126119.2C221—C226—Cl26121.3 (5)
C136—C131—C132120.6 (4)C236—C231—C232120.4 (6)
C136—C131—N112119.1 (4)C236—C231—N212119.3 (5)
C132—C131—N112120.2 (3)C232—C231—N212120.1 (5)
C133—C132—C131119.2 (4)C233—C232—C231119.0 (6)
C133—C132—H132120.4C233—C232—H232120.5
C131—C132—H132120.4C231—C232—H232120.5
C134—C133—C132120.8 (4)C234—C233—C232120.5 (5)
C134—C133—H133119.6C234—C233—H233119.8
C132—C133—H133119.6C232—C233—H233119.8
C133—C134—C135119.4 (3)C233—C234—C235119.3 (5)
C133—C134—H134120.3C233—C234—H234120.4
C135—C134—H134120.3C235—C234—H234120.4
C134—C135—C136121.6 (4)C234—C235—C236121.3 (6)
C134—C135—H135119.2C234—C235—H235119.3
C136—C135—H135119.2C236—C235—H235119.3
C131—C136—C135118.2 (5)C231—C236—C235118.0 (7)
C131—C136—H136120.9C231—C236—H236121.0
C135—C136—H136120.9C235—C236—H236121.0
O11—C11—N11—C11421 (3)O21—C21—N21—C21439 (4)
C12—C11—N11—C114175.3 (8)C22—C21—N21—C214162.3 (13)
O11—C11—C12—C1218 (3)O21—C21—C22—C2219 (4)
N11—C11—C12—C121154.8 (9)N21—C21—C22—C221167.1 (14)
C115—N111—N112—C1139 (2)C215—N211—N212—C2133 (3)
C116—N111—N112—C113144 (2)C216—N211—N212—C213137 (3)
C115—N111—N112—C131163 (2)C215—N211—N212—C231157 (3)
C116—N111—N112—C13162.8 (19)C216—N211—N212—C23169 (3)
N111—N112—C113—O113174.6 (13)N211—N212—C213—O213171 (2)
C131—N112—C113—O11323.6 (15)C231—N212—C213—O21320 (3)
N111—N112—C113—C1147.2 (13)N211—N212—C213—C2143 (2)
C131—N112—C113—C114158.2 (11)C231—N212—C213—C214153.7 (18)
C11—N11—C114—C11579 (3)C21—N21—C214—C21544 (5)
C11—N11—C114—C113102.8 (15)C21—N21—C214—C213128 (2)
O113—C113—C114—C115180 (2)O213—C213—C214—C215172 (4)
N112—C113—C114—C1152 (2)N212—C213—C214—C2151 (4)
O113—C113—C114—N111 (2)O213—C213—C214—N211 (3)
N112—C113—C114—N11176.6 (11)N212—C213—C214—N21173.9 (18)
N11—C114—C115—N111177.5 (16)N21—C214—C215—N211172 (3)
C113—C114—C115—N1114 (3)C213—C214—C215—N2111 (5)
N11—C114—C115—C1171 (6)N21—C214—C215—C21712 (9)
C113—C114—C115—C117178 (4)C213—C214—C215—C217175 (6)
N112—N111—C115—C1148 (3)N212—N211—C215—C2142 (5)
C116—N111—C115—C114140 (3)C216—N211—C215—C214134 (5)
N112—N111—C115—C117174 (3)N212—N211—C215—C217174 (5)
C116—N111—C115—C11742 (3)C216—N211—C215—C21742 (5)
C11—C12—C121—C12267.3 (7)C21—C22—C221—C22296.8 (11)
C11—C12—C121—C126115.0 (6)C21—C22—C221—C22687.3 (11)
C126—C121—C122—C1230.4 (14)C226—C221—C222—C2232 (2)
C12—C121—C122—C123177.3 (10)C22—C221—C222—C223174.4 (17)
C126—C121—C122—Cl12179.5 (6)C221—C222—C223—C2242 (4)
C12—C121—C122—Cl121.7 (10)C222—C223—C224—C2251 (6)
C121—C122—C123—C1241 (3)C223—C224—C225—C2267 (7)
Cl12—C122—C123—C124179.9 (19)C224—C225—C226—C22111 (5)
C122—C123—C124—C1251 (4)C224—C225—C226—Cl26178 (3)
C123—C124—C125—C1264 (4)C222—C221—C226—C2258 (3)
C124—C125—C126—C1214 (3)C22—C221—C226—C225168.2 (19)
C122—C121—C126—C1251.9 (15)C222—C221—C226—Cl26178.6 (11)
C12—C121—C126—C125179.6 (12)C22—C221—C226—Cl262.6 (17)
C113—N112—C131—C13656 (3)C213—N212—C231—C23656 (4)
N111—N112—C131—C136155 (2)N211—N212—C231—C236155 (4)
C113—N112—C131—C132127.2 (19)C213—N212—C231—C232118 (3)
N111—N112—C131—C13222 (2)N211—N212—C231—C23231 (3)
C136—C131—C132—C1334 (3)C236—C231—C232—C23310 (5)
N112—C131—C132—C133179.1 (13)N212—C231—C232—C233176 (2)
C131—C132—C133—C1344 (2)C231—C232—C233—C23412 (4)
C132—C133—C134—C1350 (3)C232—C233—C234—C2353 (5)
C133—C134—C135—C1364 (4)C233—C234—C235—C2369 (6)
C132—C131—C136—C1351 (4)C232—C231—C236—C2351 (7)
N112—C131—C136—C135177 (2)N212—C231—C236—C235173 (4)
C134—C135—C136—C1314 (5)C234—C235—C236—C23110 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O113i0.82 (7)2.15 (8)2.94 (2)162 (6)
N11—H11···O213i0.82 (7)2.08 (8)2.88 (2)168 (6)
N21—H21···O113i0.92 (10)2.00 (10)2.91 (2)161 (7)
N21—H21···O213i0.92 (10)1.95 (10)2.82 (3)158 (7)
C134—H134···O11ii0.932.573.46 (4)159
C234—H234···O21ii0.932.493.40 (7)164
C225—H225···O213iii0.932.393.28 (2)160
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+3/2, y+1/2, z+1/2; (iii) x+1, y1, z+1/2.
Selected torsion angles (°) for compounds (I)–(III) top
Parameter(I)(II)(III)
x = 1x = 2x = 1x = 2x = 1x = 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···AD—HH···AD···AD—H···A
(I)N11—H11···O2130.87 (3)1.93 (2)2.781 (2)169 (2)
N21—H21···O1130.84 (2)2.01 (2)2.845 (2)178 (4)
C133—H133···O11i0.932.523.446 (3)171
(II)N11—H11···O113ii0.82 (7)2.15 (8)2.94 (2)162 (6)
N11—H11···O213ii0.82 (7)2.08 (8)2.88 (2)168 (6)
N21—H21···O113ii0.92 (10)2.00 (10)2.91 (2)161 (7)
N21—H21···O213ii0.92 (10)1.95 (10)2.82 (3)158 (7)
C134—H134···O11iii0.932.573.46 (4)159
C234—H234···O21iii0.932.493.40 (7)164
C225—H225···O213iv0.932.393.28 (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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