3-(4-Bromo­phen­yl)-5-(2-chlorophen­yl)-1-phenyl-2-pyrazoline

In the title compound, C₂₁H₁₆BrClN₂, the pyrazolinyl ring is approximately perpendicular to the chloro­phenyl ring, with a dihedral angle of 82.08°.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.041
• wR factor = 0.108
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of Tmax/Tmin expected RT(exp) is > 1.10
            Absorption corrections should be applied.
            Tmin and Tmax expected:      0.573     0.651
            RT(exp) =      1.137
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) ...       1.14
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)        3000 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C21H16BrClN2	Z = 2
Mr = 411.72	F(000) = 416
Triclinic, P1	Dx = 1.485 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4440 (17) Å	Cell parameters from 25 reflections
b = 9.4810 (19) Å	θ = 4–14°
c = 11.780 (2) Å	µ = 2.38 mm^−1
α = 89.64 (3)°	T = 295 K
β = 80.73 (3)°	Block, yellow
γ = 81.73 (3)°	0.25 × 0.20 × 0.18 mm
V = 920.9 (3) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.031
Radiation source: fine-focus sealed tube	θmax = 27.0°, θmin = 1.8°
Graphite monochromator	h = 0→10
ω scans	k = −11→11
4260 measured reflections	l = −14→14
3986 independent reflections	3 standard reflections every 100 reflections
2624 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0499P)^2 + 0.358P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3986 reflections	Δρmax = 0.32 e Å^−3
227 parameters	Δρmin = −0.49 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.126 (5)

Special details

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
Br1	−0.58746 (4)	1.32813 (4)	0.64385 (4)	0.0713 (2)
Cl1	0.25816 (13)	0.39250 (10)	0.33899 (10)	0.0775 (3)
N1	0.1281 (3)	0.8247 (2)	0.2096 (2)	0.0490 (6)
N2	0.0105 (3)	0.9374 (2)	0.2509 (2)	0.0437 (6)
C1	−0.2491 (4)	0.9743 (3)	0.5328 (3)	0.0471 (7)
H1A	−0.2090	0.8891	0.5645	0.057*
C2	−0.3677 (4)	1.0701 (3)	0.5993 (3)	0.0521 (8)
H2B	−0.4071	1.0493	0.6750	0.063*
C3	−0.4261 (3)	1.1965 (3)	0.5514 (3)	0.0486 (7)
C4	−0.3721 (4)	1.2286 (3)	0.4390 (3)	0.0522 (8)
H4A	−0.4140	1.3135	0.4077	0.063*
C5	−0.2542 (4)	1.1322 (3)	0.3732 (3)	0.0473 (7)
H5A	−0.2174	1.1528	0.2970	0.057*
C6	−0.1897 (3)	1.0044 (3)	0.4196 (2)	0.0407 (6)
C7	−0.0594 (3)	0.9051 (3)	0.3512 (2)	0.0394 (6)
C8	0.0113 (4)	0.7622 (3)	0.3925 (2)	0.0439 (7)
H8A	−0.0724	0.7034	0.4175	0.053*
H8B	0.0710	0.7730	0.4550	0.053*
C9	0.1251 (3)	0.6992 (3)	0.2836 (2)	0.0419 (7)
H9A	0.2337	0.6661	0.3013	0.050*
C10	0.0600 (3)	0.5788 (3)	0.2297 (2)	0.0406 (6)
C11	−0.0605 (4)	0.6071 (3)	0.1621 (3)	0.0518 (8)
H11A	−0.0959	0.7010	0.1447	0.062*
C12	−0.1294 (4)	0.4982 (4)	0.1197 (3)	0.0627 (9)
H12A	−0.2116	0.5197	0.0758	0.075*
C13	−0.0763 (5)	0.3581 (4)	0.1427 (3)	0.0671 (10)
H13A	−0.1222	0.2852	0.1140	0.080*
C14	0.0444 (5)	0.3263 (4)	0.2080 (3)	0.0621 (9)
H14A	0.0822	0.2320	0.2226	0.075*
C15	0.1091 (4)	0.4367 (3)	0.2519 (3)	0.0466 (7)
C16	0.2317 (3)	0.8334 (3)	0.1058 (2)	0.0414 (7)
C17	0.2139 (4)	0.9517 (3)	0.0359 (3)	0.0502 (8)
H17A	0.1314	1.0270	0.0582	0.060*
C18	0.3182 (5)	0.9573 (4)	−0.0665 (3)	0.0646 (9)
H18A	0.3054	1.0368	−0.1126	0.077*
C19	0.4420 (4)	0.8459 (4)	−0.1014 (3)	0.0670 (10)
H19A	0.5117	0.8503	−0.1706	0.080*
C20	0.4603 (4)	0.7293 (4)	−0.0325 (3)	0.0621 (9)
H20A	0.5437	0.6548	−0.0555	0.075*
C21	0.3572 (4)	0.7204 (3)	0.0703 (3)	0.0540 (8)
H21A	0.3706	0.6404	0.1157	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0493 (2)	0.0783 (3)	0.0806 (3)	0.00068 (16)	−0.00063 (16)	−0.0292 (2)
Cl1	0.0850 (7)	0.0541 (5)	0.1018 (8)	−0.0106 (5)	−0.0412 (6)	0.0235 (5)
N1	0.0575 (15)	0.0348 (13)	0.0493 (16)	−0.0054 (11)	0.0066 (12)	0.0010 (11)
N2	0.0461 (13)	0.0358 (13)	0.0472 (16)	−0.0065 (10)	−0.0009 (11)	−0.0033 (11)
C1	0.0578 (17)	0.0381 (16)	0.0448 (18)	−0.0107 (13)	−0.0029 (14)	0.0009 (13)
C2	0.0576 (18)	0.056 (2)	0.0413 (18)	−0.0188 (15)	0.0051 (14)	−0.0051 (15)
C3	0.0396 (14)	0.0521 (18)	0.053 (2)	−0.0092 (13)	−0.0029 (13)	−0.0113 (15)
C4	0.0480 (16)	0.0475 (18)	0.060 (2)	−0.0010 (13)	−0.0112 (15)	0.0004 (15)
C5	0.0478 (16)	0.0525 (18)	0.0418 (17)	−0.0088 (14)	−0.0063 (13)	0.0029 (14)
C6	0.0441 (15)	0.0396 (15)	0.0394 (16)	−0.0111 (12)	−0.0052 (12)	−0.0046 (12)
C7	0.0446 (15)	0.0356 (15)	0.0398 (17)	−0.0112 (11)	−0.0074 (13)	−0.0008 (12)
C8	0.0538 (16)	0.0385 (15)	0.0402 (17)	−0.0118 (12)	−0.0054 (13)	−0.0016 (13)
C9	0.0446 (15)	0.0370 (15)	0.0444 (17)	−0.0077 (12)	−0.0059 (13)	0.0000 (13)
C10	0.0420 (14)	0.0399 (15)	0.0382 (16)	−0.0077 (12)	0.0003 (12)	−0.0047 (12)
C11	0.0520 (17)	0.0546 (19)	0.0472 (18)	−0.0041 (14)	−0.0064 (14)	−0.0053 (15)
C12	0.060 (2)	0.084 (3)	0.049 (2)	−0.0201 (18)	−0.0116 (16)	−0.0085 (18)
C13	0.084 (3)	0.069 (3)	0.055 (2)	−0.040 (2)	−0.0039 (19)	−0.0146 (19)
C14	0.081 (2)	0.0431 (18)	0.062 (2)	−0.0196 (16)	−0.0023 (19)	−0.0036 (16)
C15	0.0511 (16)	0.0421 (17)	0.0459 (18)	−0.0091 (13)	−0.0036 (13)	0.0007 (13)
C16	0.0437 (15)	0.0404 (15)	0.0413 (17)	−0.0125 (12)	−0.0044 (12)	−0.0039 (13)
C17	0.0595 (18)	0.0463 (18)	0.0444 (18)	−0.0114 (14)	−0.0033 (15)	−0.0030 (14)
C18	0.078 (2)	0.063 (2)	0.052 (2)	−0.0157 (18)	−0.0030 (18)	0.0079 (17)
C19	0.063 (2)	0.083 (3)	0.051 (2)	−0.0135 (19)	0.0085 (17)	0.0005 (19)
C20	0.0517 (18)	0.069 (2)	0.059 (2)	−0.0028 (16)	0.0041 (16)	−0.0047 (19)
C21	0.0533 (18)	0.0538 (19)	0.052 (2)	−0.0052 (14)	−0.0018 (15)	0.0045 (15)

Geometric parameters (Å, º)

Br1—C3	1.911 (3)	C9—H9A	0.9800
Cl1—C15	1.753 (3)	C10—C11	1.387 (4)
N1—N2	1.382 (3)	C10—C15	1.387 (4)
N1—C16	1.393 (4)	C11—C12	1.388 (5)
N1—C9	1.472 (4)	C11—H11A	0.9300
N2—C7	1.289 (4)	C12—C13	1.379 (5)
C1—C6	1.391 (4)	C12—H12A	0.9300
C1—C2	1.391 (4)	C13—C14	1.371 (5)
C1—H1A	0.9300	C13—H13A	0.9300
C2—C3	1.382 (5)	C14—C15	1.387 (4)
C2—H2B	0.9300	C14—H14A	0.9300
C3—C4	1.376 (5)	C16—C17	1.392 (4)
C4—C5	1.388 (4)	C16—C21	1.407 (4)
C4—H4A	0.9300	C17—C18	1.380 (5)
C5—C6	1.400 (4)	C17—H17A	0.9300
C5—H5A	0.9300	C18—C19	1.388 (5)
C6—C7	1.474 (4)	C18—H18A	0.9300
C7—C8	1.511 (4)	C19—C20	1.373 (5)
C8—C9	1.540 (4)	C19—H19A	0.9300
C8—H8A	0.9700	C20—C21	1.384 (5)
C8—H8B	0.9700	C20—H20A	0.9300
C9—C10	1.520 (4)	C21—H21A	0.9300
N2—N1—C16	121.1 (2)	C11—C10—C15	116.8 (3)
N2—N1—C9	113.0 (2)	C11—C10—C9	121.0 (3)
C16—N1—C9	125.8 (2)	C15—C10—C9	122.1 (3)
C7—N2—N1	108.3 (2)	C10—C11—C12	121.4 (3)
C6—C1—C2	120.8 (3)	C10—C11—H11A	119.3
C6—C1—H1A	119.6	C12—C11—H11A	119.3
C2—C1—H1A	119.6	C13—C12—C11	120.1 (3)
C3—C2—C1	119.1 (3)	C13—C12—H12A	119.9
C3—C2—H2B	120.5	C11—C12—H12A	119.9
C1—C2—H2B	120.5	C14—C13—C12	120.0 (3)
C4—C3—C2	121.6 (3)	C14—C13—H13A	120.0
C4—C3—Br1	119.6 (2)	C12—C13—H13A	120.0
C2—C3—Br1	118.8 (2)	C13—C14—C15	119.1 (3)
C3—C4—C5	118.9 (3)	C13—C14—H14A	120.5
C3—C4—H4A	120.6	C15—C14—H14A	120.5
C5—C4—H4A	120.6	C14—C15—C10	122.6 (3)
C4—C5—C6	121.1 (3)	C14—C15—Cl1	117.9 (3)
C4—C5—H5A	119.5	C10—C15—Cl1	119.5 (2)
C6—C5—H5A	119.5	C17—C16—N1	121.4 (3)
C1—C6—C5	118.5 (3)	C17—C16—C21	119.0 (3)
C1—C6—C7	120.5 (3)	N1—C16—C21	119.5 (3)
C5—C6—C7	121.0 (3)	C18—C17—C16	120.2 (3)
N2—C7—C6	121.8 (3)	C18—C17—H17A	119.9
N2—C7—C8	113.7 (2)	C16—C17—H17A	119.9
C6—C7—C8	124.4 (3)	C17—C18—C19	120.8 (3)
C7—C8—C9	101.9 (2)	C17—C18—H18A	119.6
C7—C8—H8A	111.4	C19—C18—H18A	119.6
C9—C8—H8A	111.4	C20—C19—C18	119.2 (3)
C7—C8—H8B	111.4	C20—C19—H19A	120.4
C9—C8—H8B	111.4	C18—C19—H19A	120.4
H8A—C8—H8B	109.2	C19—C20—C21	121.2 (3)
N1—C9—C10	112.1 (2)	C19—C20—H20A	119.4
N1—C9—C8	101.4 (2)	C21—C20—H20A	119.4
C10—C9—C8	112.2 (2)	C20—C21—C16	119.6 (3)
N1—C9—H9A	110.3	C20—C21—H21A	120.2
C10—C9—H9A	110.3	C16—C21—H21A	120.2
C8—C9—H9A	110.3