1-Acetyl-5-(2,6-dichloro­phen­yl)-3-(2-naphth­yl)-2-pyrazoline

In the title compound, C₂₁H₁₆Cl₂N₂O, the pendant benzene ring and the naphthalene ring system make dihedral angles of 82.9 (3) and 6.7 (3)°, respectively, with the central pyrazoline ring.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.109
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.75 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.24 Ratio
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C21

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

1-Acetyl-5-(2,6-dichlorophenyl)-3-(2-naphthyl)-2-pyrazoline

Crystal data

C21H16Cl2N2O	F(000) = 792
Mr = 383.26	Dx = 1.357 Mg m^−3
Monoclinic, P21/c	Melting point = 513–514 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.749 (2) Å	Cell parameters from 2244 reflections
b = 12.763 (3) Å	θ = 2.2–22.7°
c = 14.629 (3) Å	µ = 0.36 mm^−1
β = 110.798 (3)°	T = 294 K
V = 1876.1 (7) Å^3	Block, colorless
Z = 4	0.26 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer	3817 independent reflections
Radiation source: fine-focus sealed tube	2170 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
ω scans	θmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −12→13
Tmin = 0.913, Tmax = 0.932	k = −7→15
10324 measured reflections	l = −17→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0356P)^2 + 0.4418P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.002
3817 reflections	Δρmax = 0.21 e Å^−3
237 parameters	Δρmin = −0.32 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0404 (18)

Special details

Experimental. ¹H NMR (CDCl₃): 8.10 (dd, 1H), 7.93 (s, 1H), 7.89–7.84 (m, 3H), 7.55–7.52 (m, 2H), 7.38 (dd, 1H), 7.27 (dd, 1H), 7.12 (t, 1H), 6.27 (dd, 1H),3.80 (dd, 1H), 3.42 (dd, 1H), 2.42 (s, 3H).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.52114 (7)	0.34014 (6)	0.10576 (6)	0.0818 (3)
Cl2	0.16570 (8)	0.01938 (6)	−0.01546 (6)	0.0881 (3)
O1	0.3096 (2)	0.20676 (15)	−0.17390 (13)	0.0738 (6)
N1	0.27312 (19)	0.32739 (14)	−0.07557 (13)	0.0431 (5)
N2	0.25428 (19)	0.43131 (14)	−0.05486 (13)	0.0438 (5)
C1	0.4785 (2)	0.2073 (2)	0.09388 (17)	0.0497 (6)
C2	0.5792 (3)	0.1376 (2)	0.1414 (2)	0.0675 (8)
H2	0.6652	0.1617	0.1742	0.081*
C3	0.5513 (3)	0.0325 (3)	0.1397 (2)	0.0691 (8)
H3	0.6185	−0.0148	0.1718	0.083*
C4	0.4250 (3)	−0.0028 (2)	0.09106 (18)	0.0597 (7)
H4	0.4056	−0.0738	0.0903	0.072*
C5	0.3258 (2)	0.06875 (19)	0.04263 (16)	0.0467 (6)
C6	0.3488 (2)	0.17589 (17)	0.04094 (15)	0.0373 (5)
C7	0.2375 (2)	0.25151 (16)	−0.01218 (15)	0.0376 (5)
H7	0.1601	0.2110	−0.0526	0.045*
C8	0.1940 (2)	0.32525 (17)	0.05376 (16)	0.0403 (6)
H8A	0.1020	0.3130	0.0466	0.048*
H8B	0.2498	0.3165	0.1219	0.048*
C9	0.2116 (2)	0.43244 (17)	0.01712 (16)	0.0354 (5)
C10	0.1859 (2)	0.53160 (18)	0.05790 (15)	0.0380 (5)
C11	0.1310 (2)	0.53197 (19)	0.12966 (16)	0.0420 (6)
H11	0.1092	0.4686	0.1515	0.050*
C12	0.1069 (2)	0.6266 (2)	0.17121 (16)	0.0444 (6)
C13	0.0534 (3)	0.6283 (2)	0.24612 (19)	0.0621 (8)
H13	0.0284	0.5658	0.2674	0.075*
C14	0.0379 (3)	0.7211 (3)	0.2880 (2)	0.0793 (10)
H14	0.0018	0.7211	0.3371	0.095*
C15	0.0757 (3)	0.8155 (3)	0.2575 (2)	0.0803 (10)
H15	0.0670	0.8778	0.2878	0.096*
C16	0.1249 (3)	0.8173 (2)	0.1842 (2)	0.0687 (8)
H16	0.1473	0.8809	0.1632	0.082*
C17	0.1425 (2)	0.7228 (2)	0.13920 (17)	0.0496 (7)
C18	0.1969 (3)	0.7205 (2)	0.06421 (19)	0.0582 (7)
H18	0.2185	0.7832	0.0411	0.070*
C19	0.2184 (3)	0.62883 (19)	0.02524 (18)	0.0514 (6)
H19	0.2549	0.6298	−0.0236	0.062*
C20	0.3078 (3)	0.2993 (2)	−0.15304 (18)	0.0575 (7)
C21	0.3435 (4)	0.3868 (2)	−0.2076 (2)	0.0972 (12)
H21A	0.3657	0.3585	−0.2607	0.146*
H21B	0.4185	0.4245	−0.1641	0.146*
H21C	0.2692	0.4336	−0.2330	0.146*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0523 (4)	0.0641 (5)	0.1115 (7)	−0.0182 (4)	0.0075 (4)	−0.0063 (5)
Cl2	0.0799 (5)	0.0452 (4)	0.1053 (7)	−0.0202 (4)	−0.0087 (4)	0.0087 (4)
O1	0.1233 (17)	0.0497 (12)	0.0629 (12)	0.0110 (11)	0.0509 (12)	−0.0061 (10)
N1	0.0624 (13)	0.0345 (12)	0.0391 (11)	0.0015 (10)	0.0263 (10)	−0.0006 (9)
N2	0.0591 (12)	0.0341 (11)	0.0423 (12)	−0.0002 (10)	0.0229 (10)	−0.0003 (9)
C1	0.0425 (14)	0.0523 (16)	0.0517 (15)	0.0001 (12)	0.0138 (12)	−0.0051 (13)
C2	0.0462 (16)	0.079 (2)	0.0668 (19)	0.0139 (15)	0.0069 (14)	−0.0065 (17)
C3	0.067 (2)	0.076 (2)	0.0536 (18)	0.0336 (17)	0.0094 (15)	0.0015 (17)
C4	0.085 (2)	0.0402 (16)	0.0475 (16)	0.0165 (14)	0.0158 (15)	0.0030 (13)
C5	0.0565 (15)	0.0408 (15)	0.0374 (14)	0.0001 (12)	0.0100 (12)	−0.0031 (12)
C6	0.0409 (13)	0.0406 (14)	0.0312 (12)	0.0016 (11)	0.0140 (10)	−0.0012 (11)
C7	0.0402 (13)	0.0338 (13)	0.0375 (13)	−0.0038 (10)	0.0122 (11)	0.0002 (11)
C8	0.0425 (13)	0.0398 (14)	0.0422 (13)	−0.0006 (11)	0.0195 (11)	0.0009 (11)
C9	0.0349 (12)	0.0361 (13)	0.0355 (13)	−0.0017 (10)	0.0130 (10)	0.0009 (11)
C10	0.0371 (12)	0.0388 (14)	0.0356 (13)	−0.0016 (10)	0.0096 (10)	−0.0030 (11)
C11	0.0426 (13)	0.0427 (14)	0.0412 (13)	−0.0046 (11)	0.0154 (11)	−0.0052 (12)
C12	0.0359 (13)	0.0549 (16)	0.0372 (13)	0.0055 (12)	0.0064 (11)	−0.0094 (13)
C13	0.0599 (17)	0.076 (2)	0.0546 (16)	−0.0002 (15)	0.0259 (14)	−0.0154 (16)
C14	0.075 (2)	0.105 (3)	0.0604 (19)	0.018 (2)	0.0280 (16)	−0.025 (2)
C15	0.089 (2)	0.073 (2)	0.066 (2)	0.0306 (19)	0.0119 (18)	−0.0209 (19)
C16	0.082 (2)	0.0515 (18)	0.0590 (18)	0.0203 (15)	0.0089 (16)	−0.0078 (15)
C17	0.0480 (15)	0.0458 (16)	0.0431 (15)	0.0124 (12)	0.0013 (12)	−0.0054 (13)
C18	0.0751 (19)	0.0384 (16)	0.0587 (17)	0.0011 (13)	0.0210 (15)	0.0036 (14)
C19	0.0667 (17)	0.0441 (15)	0.0482 (15)	0.0002 (13)	0.0264 (13)	0.0029 (13)
C20	0.084 (2)	0.0516 (18)	0.0462 (16)	0.0088 (15)	0.0338 (15)	−0.0008 (14)
C21	0.179 (4)	0.068 (2)	0.084 (2)	−0.002 (2)	0.095 (3)	0.0051 (19)

Geometric parameters (Å, º)

Cl1—C1	1.749 (3)	C10—C11	1.375 (3)
Cl2—C5	1.744 (2)	C10—C19	1.417 (3)
O1—C20	1.221 (3)	C11—C12	1.417 (3)
N1—C20	1.361 (3)	C11—H11	0.9300
N1—N2	1.391 (2)	C12—C13	1.407 (3)
N1—C7	1.482 (3)	C12—C17	1.413 (3)
N2—C9	1.289 (3)	C13—C14	1.371 (4)
C1—C2	1.383 (3)	C13—H13	0.9300
C1—C6	1.392 (3)	C14—C15	1.395 (4)
C2—C3	1.372 (4)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.354 (4)
C3—C4	1.366 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.419 (3)
C4—C5	1.392 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.415 (3)
C5—C6	1.391 (3)	C18—C19	1.356 (3)
C6—C7	1.519 (3)	C18—H18	0.9300
C7—C8	1.535 (3)	C19—H19	0.9300
C7—H7	0.9800	C20—C21	1.501 (4)
C8—C9	1.505 (3)	C21—H21A	0.9600
C8—H8A	0.9700	C21—H21B	0.9600
C8—H8B	0.9700	C21—H21C	0.9600
C9—C10	1.467 (3)
C20—N1—N2	122.5 (2)	C11—C10—C9	120.5 (2)
C20—N1—C7	123.83 (19)	C19—C10—C9	120.9 (2)
N2—N1—C7	113.38 (16)	C10—C11—C12	121.6 (2)
C9—N2—N1	108.05 (18)	C10—C11—H11	119.2
C2—C1—C6	123.0 (2)	C12—C11—H11	119.2
C2—C1—Cl1	116.3 (2)	C13—C12—C17	118.6 (2)
C6—C1—Cl1	120.63 (19)	C13—C12—C11	122.3 (2)
C3—C2—C1	119.5 (3)	C17—C12—C11	119.0 (2)
C3—C2—H2	120.2	C14—C13—C12	120.6 (3)
C1—C2—H2	120.2	C14—C13—H13	119.7
C4—C3—C2	120.1 (3)	C12—C13—H13	119.7
C4—C3—H3	119.9	C13—C14—C15	120.6 (3)
C2—C3—H3	119.9	C13—C14—H14	119.7
C3—C4—C5	119.3 (3)	C15—C14—H14	119.7
C3—C4—H4	120.3	C16—C15—C14	120.5 (3)
C5—C4—H4	120.3	C16—C15—H15	119.7
C6—C5—C4	123.0 (2)	C14—C15—H15	119.7
C6—C5—Cl2	119.85 (18)	C15—C16—C17	120.5 (3)
C4—C5—Cl2	117.2 (2)	C15—C16—H16	119.8
C5—C6—C1	115.0 (2)	C17—C16—H16	119.8
C5—C6—C7	121.4 (2)	C12—C17—C18	118.3 (2)
C1—C6—C7	123.6 (2)	C12—C17—C16	119.2 (2)
N1—C7—C6	113.82 (17)	C18—C17—C16	122.5 (3)
N1—C7—C8	101.33 (16)	C19—C18—C17	121.5 (2)
C6—C7—C8	115.38 (17)	C19—C18—H18	119.3
N1—C7—H7	108.6	C17—C18—H18	119.3
C6—C7—H7	108.6	C18—C19—C10	121.0 (2)
C8—C7—H7	108.6	C18—C19—H19	119.5
C9—C8—C7	103.22 (16)	C10—C19—H19	119.5
C9—C8—H8A	111.1	O1—C20—N1	119.7 (2)
C7—C8—H8A	111.1	O1—C20—C21	123.9 (2)
C9—C8—H8B	111.1	N1—C20—C21	116.4 (2)
C7—C8—H8B	111.1	C20—C21—H21A	109.5
H8A—C8—H8B	109.1	C20—C21—H21B	109.5
N2—C9—C10	121.0 (2)	H21A—C21—H21B	109.5
N2—C9—C8	114.00 (19)	C20—C21—H21C	109.5
C10—C9—C8	125.02 (19)	H21A—C21—H21C	109.5
C11—C10—C19	118.6 (2)	H21B—C21—H21C	109.5
C20—N1—N2—C9	174.7 (2)	C7—C8—C9—C10	−178.61 (19)
C7—N1—N2—C9	1.0 (2)	N2—C9—C10—C11	175.1 (2)
C6—C1—C2—C3	−2.1 (4)	C8—C9—C10—C11	−5.8 (3)
Cl1—C1—C2—C3	176.5 (2)	N2—C9—C10—C19	−5.7 (3)
C1—C2—C3—C4	0.3 (4)	C8—C9—C10—C19	173.4 (2)
C2—C3—C4—C5	0.6 (4)	C19—C10—C11—C12	−0.1 (3)
C3—C4—C5—C6	0.2 (4)	C9—C10—C11—C12	179.13 (19)
C3—C4—C5—Cl2	−178.4 (2)	C10—C11—C12—C13	−178.6 (2)
C4—C5—C6—C1	−1.8 (3)	C10—C11—C12—C17	−1.2 (3)
Cl2—C5—C6—C1	176.76 (16)	C17—C12—C13—C14	−0.9 (4)
C4—C5—C6—C7	−179.6 (2)	C11—C12—C13—C14	176.6 (2)
Cl2—C5—C6—C7	−1.0 (3)	C12—C13—C14—C15	−0.4 (4)
C2—C1—C6—C5	2.7 (3)	C13—C14—C15—C16	1.8 (5)
Cl1—C1—C6—C5	−175.76 (18)	C14—C15—C16—C17	−1.9 (4)
C2—C1—C6—C7	−179.6 (2)	C13—C12—C17—C18	179.6 (2)
Cl1—C1—C6—C7	2.0 (3)	C11—C12—C17—C18	2.1 (3)
C20—N1—C7—C6	61.3 (3)	C13—C12—C17—C16	0.8 (3)
N2—N1—C7—C6	−125.14 (19)	C11—C12—C17—C16	−176.7 (2)
C20—N1—C7—C8	−174.2 (2)	C15—C16—C17—C12	0.6 (4)
N2—N1—C7—C8	−0.6 (2)	C15—C16—C17—C18	−178.2 (2)
C5—C6—C7—N1	−132.8 (2)	C12—C17—C18—C19	−1.8 (4)
C1—C6—C7—N1	49.6 (3)	C16—C17—C18—C19	177.0 (2)
C5—C6—C7—C8	110.7 (2)	C17—C18—C19—C10	0.5 (4)
C1—C6—C7—C8	−66.9 (3)	C11—C10—C19—C18	0.5 (3)
N1—C7—C8—C9	0.1 (2)	C9—C10—C19—C18	−178.7 (2)
C6—C7—C8—C9	123.53 (19)	N2—N1—C20—O1	−172.4 (2)
N1—N2—C9—C10	178.23 (18)	C7—N1—C20—O1	0.6 (4)
N1—N2—C9—C8	−0.9 (3)	N2—N1—C20—C21	8.2 (4)
C7—C8—C9—N2	0.5 (2)	C7—N1—C20—C21	−178.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1^i	0.93	2.57	3.359 (4)	143

Symmetry code: (i) −x+1, −y, −z.