4-(3-Bromo-5-chloro-2-hydroxy­benzyl­ideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

The title compound, C₁₈H₁₅BrClN₃O₂, was obtained by reacting 3-bromo-5-chloro­salicylic aldehyde and 4-amino­anti­pyrine. The structure displays a trans configuration about the imine C=N double bond. The N atom is also involved in an intra­molecular O—H...N hydrogen bond, which stabilizes the configuration.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.047
• wR factor = 0.110
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.683     0.881
            Tmin and Tmax expected:      0.554     0.881
            RR =      1.234
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.24
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  O2      ..       3.02 Ang.

   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
   2 ALERT type 3 Indicator that the structure quality may be low
   0 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, 2000); cell refinement: SAINT (Bruker, 2000); 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, 2000); software used to prepare material for publication: SHELXTL.

4-(3-Bromo-5-chloro-2-hydroxybenzylideneamino)-1,5-dimethyl-2-phenyl- 1H-pyrazol-3(2H)-one

Crystal data

C18H15BrClN3O2	F(000) = 848
Mr = 420.69	Dx = 1.602 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1768 reflections
a = 7.055 (2) Å	θ = 2.6–22.2°
b = 8.058 (3) Å	µ = 2.53 mm^−1
c = 30.691 (10) Å	T = 298 K
β = 91.716 (4)°	Plate, colourless
V = 1744.1 (10) Å^3	0.50 × 0.20 × 0.05 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3070 independent reflections
Radiation source: fine-focus sealed tube	2283 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.683, Tmax = 0.881	k = −5→9
6896 measured reflections	l = −36→36

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0515P)^2 + 0.3363P] where P = (Fo^2 + 2Fc^2)/3
3070 reflections	(Δ/σ)max = 0.003
228 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.40727 (6)	0.34654 (6)	1.140044 (14)	0.06052 (19)
C1	0.7240 (5)	0.1832 (4)	1.10665 (13)	0.0438 (9)
H1	0.7628	0.1745	1.1358	0.053*
C2	0.8351 (5)	0.1201 (4)	1.07424 (13)	0.0396 (9)
C3	0.7790 (5)	0.1325 (4)	1.03141 (13)	0.0429 (10)
H3	0.8548	0.0889	1.0099	0.052*
C4	0.6075 (5)	0.2105 (4)	1.01968 (12)	0.0377 (9)
C5	0.4944 (5)	0.2761 (5)	1.05215 (12)	0.0387 (9)
C6	0.5551 (5)	0.2590 (5)	1.09509 (12)	0.0421 (9)
C7	0.5502 (5)	0.2182 (5)	0.97399 (13)	0.0424 (9)
H7	0.6271	0.1697	0.9535	0.051*
C8	0.3434 (5)	0.2939 (4)	0.91707 (12)	0.0357 (8)
C9	0.4486 (5)	0.2307 (5)	0.88106 (12)	0.0380 (9)
C10	0.1794 (5)	0.3604 (4)	0.90094 (12)	0.0379 (9)
C11	0.4017 (5)	0.2795 (5)	0.80141 (12)	0.0376 (9)
C12	0.5281 (5)	0.1611 (5)	0.78634 (13)	0.0459 (10)
H12	0.5617	0.0703	0.8036	0.055*
C13	0.6025 (6)	0.1797 (6)	0.74579 (14)	0.0561 (12)
H13	0.6911	0.1036	0.7362	0.067*
C14	0.5477 (6)	0.3093 (6)	0.71923 (15)	0.0647 (13)
H14	0.5985	0.3204	0.6918	0.078*
C15	0.4178 (6)	0.4223 (6)	0.73338 (14)	0.0604 (12)
H15	0.3766	0.5074	0.7149	0.072*
C16	0.3473 (5)	0.4106 (5)	0.77505 (12)	0.0453 (10)
H16	0.2641	0.4905	0.7851	0.054*
C17	−0.0070 (5)	0.3172 (5)	0.83254 (13)	0.0506 (11)
H17A	−0.0462	0.2058	0.8387	0.076*
H17B	0.0114	0.3290	0.8018	0.076*
H17C	−0.1028	0.3935	0.8415	0.076*
C18	0.0198 (5)	0.4322 (5)	0.92553 (13)	0.0521 (11)
H18A	−0.0898	0.3623	0.9220	0.078*
H18B	−0.0093	0.5411	0.9145	0.078*
H18C	0.0557	0.4394	0.9559	0.078*
Cl2	1.05066 (13)	0.02576 (13)	1.08890 (3)	0.0499 (3)
N1	0.3313 (4)	0.2611 (4)	0.84391 (10)	0.0391 (7)
N2	0.1723 (4)	0.3530 (4)	0.85658 (10)	0.0392 (7)
N3	0.3957 (4)	0.2904 (4)	0.96097 (10)	0.0387 (7)
O1	0.3295 (4)	0.3538 (4)	1.04233 (9)	0.0500 (7)
H1A	0.3102	0.3528	1.0158	0.075*
O2	0.6070 (3)	0.1693 (3)	0.87960 (9)	0.0515 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0569 (3)	0.0797 (4)	0.0456 (3)	0.0059 (2)	0.0124 (2)	−0.0102 (2)
C1	0.048 (2)	0.044 (2)	0.039 (2)	−0.0003 (19)	−0.0030 (18)	0.0032 (18)
C2	0.0340 (19)	0.038 (2)	0.047 (2)	0.0056 (17)	−0.0056 (17)	0.0025 (18)
C3	0.040 (2)	0.042 (2)	0.047 (2)	0.0071 (18)	0.0064 (18)	−0.0010 (18)
C4	0.036 (2)	0.039 (2)	0.039 (2)	0.0028 (17)	0.0019 (16)	0.0006 (17)
C5	0.034 (2)	0.039 (2)	0.043 (2)	−0.0002 (17)	0.0037 (17)	0.0029 (18)
C6	0.044 (2)	0.041 (2)	0.041 (2)	−0.0021 (19)	0.0091 (17)	−0.0023 (18)
C7	0.040 (2)	0.050 (2)	0.038 (2)	0.0046 (19)	0.0081 (17)	0.0030 (18)
C8	0.0315 (19)	0.040 (2)	0.036 (2)	−0.0009 (16)	0.0000 (16)	0.0022 (16)
C9	0.0298 (19)	0.045 (2)	0.039 (2)	0.0010 (18)	0.0017 (16)	0.0064 (18)
C10	0.0313 (19)	0.040 (2)	0.042 (2)	0.0021 (17)	0.0026 (16)	0.0044 (17)
C11	0.0279 (18)	0.047 (2)	0.038 (2)	−0.0012 (17)	−0.0014 (15)	−0.0020 (18)
C12	0.043 (2)	0.054 (3)	0.040 (2)	0.007 (2)	−0.0011 (18)	−0.0033 (19)
C13	0.044 (2)	0.079 (3)	0.045 (3)	0.010 (2)	0.0046 (19)	−0.013 (2)
C14	0.054 (3)	0.099 (4)	0.042 (3)	0.002 (3)	0.009 (2)	−0.001 (3)
C15	0.058 (3)	0.072 (3)	0.051 (3)	0.000 (2)	0.004 (2)	0.013 (2)
C16	0.039 (2)	0.054 (2)	0.043 (2)	0.0033 (19)	0.0038 (17)	0.004 (2)
C17	0.035 (2)	0.069 (3)	0.047 (2)	0.010 (2)	−0.0009 (18)	0.001 (2)
C18	0.041 (2)	0.062 (3)	0.054 (3)	0.013 (2)	0.0070 (19)	−0.002 (2)
Cl2	0.0404 (5)	0.0553 (6)	0.0535 (6)	0.0131 (5)	−0.0075 (4)	0.0047 (5)
N1	0.0312 (16)	0.0495 (19)	0.0369 (18)	0.0098 (15)	0.0042 (13)	0.0032 (15)
N2	0.0267 (15)	0.052 (2)	0.0392 (18)	0.0082 (14)	0.0020 (13)	0.0022 (15)
N3	0.0344 (17)	0.0421 (19)	0.0395 (19)	0.0016 (14)	0.0017 (13)	0.0049 (14)
O1	0.0427 (15)	0.0647 (19)	0.0429 (16)	0.0172 (14)	0.0037 (12)	−0.0007 (15)
O2	0.0325 (14)	0.078 (2)	0.0446 (16)	0.0195 (14)	0.0014 (11)	0.0055 (14)

Geometric parameters (Å, º)

Br1—C6	1.891 (4)	C11—C16	1.378 (5)
C1—C6	1.377 (5)	C11—C12	1.394 (5)
C1—C2	1.381 (5)	C11—N1	1.417 (4)
C1—H1	0.9300	C12—C13	1.374 (6)
C2—C3	1.365 (5)	C12—H12	0.9300
C2—Cl2	1.747 (4)	C13—C14	1.373 (6)
C3—C4	1.401 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.372 (6)
C4—C5	1.399 (5)	C14—H14	0.9300
C4—C7	1.449 (5)	C15—C16	1.389 (5)
C5—O1	1.347 (4)	C15—H15	0.9300
C5—C6	1.380 (5)	C16—H16	0.9300
C7—N3	1.288 (4)	C17—N2	1.473 (5)
C7—H7	0.9300	C17—H17A	0.9600
C8—C10	1.356 (5)	C17—H17B	0.9600
C8—N3	1.387 (5)	C17—H17C	0.9600
C8—C9	1.443 (5)	C18—H18A	0.9600
C9—O2	1.224 (4)	C18—H18B	0.9600
C9—N1	1.410 (4)	C18—H18C	0.9600
C10—N2	1.362 (5)	N1—N2	1.409 (4)
C10—C18	1.491 (5)	O1—H1A	0.8200
C6—C1—C2	118.9 (4)	C13—C12—H12	120.3
C6—C1—H1	120.6	C11—C12—H12	120.3
C2—C1—H1	120.6	C14—C13—C12	120.8 (4)
C3—C2—C1	120.8 (3)	C14—C13—H13	119.6
C3—C2—Cl2	120.3 (3)	C12—C13—H13	119.6
C1—C2—Cl2	118.9 (3)	C15—C14—C13	119.7 (4)
C2—C3—C4	120.2 (3)	C15—C14—H14	120.1
C2—C3—H3	119.9	C13—C14—H14	120.1
C4—C3—H3	119.9	C14—C15—C16	120.5 (4)
C5—C4—C3	119.6 (3)	C14—C15—H15	119.8
C5—C4—C7	121.6 (3)	C16—C15—H15	119.8
C3—C4—C7	118.8 (3)	C11—C16—C15	119.4 (4)
O1—C5—C6	120.1 (3)	C11—C16—H16	120.3
O1—C5—C4	121.6 (3)	C15—C16—H16	120.3
C6—C5—C4	118.4 (3)	N2—C17—H17A	109.5
C1—C6—C5	122.1 (4)	N2—C17—H17B	109.5
C1—C6—Br1	118.0 (3)	H17A—C17—H17B	109.5
C5—C6—Br1	119.8 (3)	N2—C17—H17C	109.5
N3—C7—C4	121.9 (3)	H17A—C17—H17C	109.5
N3—C7—H7	119.1	H17B—C17—H17C	109.5
C4—C7—H7	119.1	C10—C18—H18A	109.5
C10—C8—N3	124.2 (3)	C10—C18—H18B	109.5
C10—C8—C9	108.2 (3)	H18A—C18—H18B	109.5
N3—C8—C9	127.5 (3)	C10—C18—H18C	109.5
O2—C9—N1	123.7 (3)	H18A—C18—H18C	109.5
O2—C9—C8	131.5 (4)	H18B—C18—H18C	109.5
N1—C9—C8	104.8 (3)	N2—N1—C9	108.7 (3)
C8—C10—N2	110.7 (3)	N2—N1—C11	120.2 (3)
C8—C10—C18	128.2 (4)	C9—N1—C11	123.3 (3)
N2—C10—C18	121.2 (3)	C10—N2—N1	107.1 (3)
C16—C11—C12	120.0 (4)	C10—N2—C17	121.0 (3)
C16—C11—N1	121.4 (3)	N1—N2—C17	116.0 (3)
C12—C11—N1	118.6 (3)	C7—N3—C8	120.5 (3)
C13—C12—C11	119.4 (4)	C5—O1—H1A	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N3	0.82	1.87	2.604 (4)	148