3-(2,4-Dichloro­phen­yl)-3-hydr­oxy-1-(3-nitro­phen­yl)propan-1-one

Luo, Z.-G.

doi:10.1107/S1600536807018338

3-(2,4-Dichlorophenyl)-3-hydroxy-1-(3-nitrophenyl)propan-1-one

The title compound, C₁₅H₁₁Cl₂NO₄, has been synthesized and characterized by single-crystal X-ray diffraction analysis. All bond lengths and angles are within normal ranges. The dihedral angle between the two benzene rings is 77.2 (2)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807018338/bx2066sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807018338/bx2066Isup2.hkl Contains datablock I

CCDC reference: 646768

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Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R factor = 0.063
wR factor = 0.153
Data-to-parameter ratio = 14.5

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No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)        3000 Deg.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

   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

   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1999); software used to prepare material for publication: SHELXTL.

3-(2,4-Dichlorophenyl)-3-hydroxy-1-(3-nitrophenyl)propan-1-one top

Crystal data top

C₁₅H₁₁Cl₂NO₄	Z = 2
M_r = 340.15	F(000) = 348
Triclinic, P1	D_x = 1.505 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4440 (15) Å	Cell parameters from 2568 reflections
b = 8.5460 (17) Å	θ = 4.2–26°
c = 12.257 (3) Å	µ = 0.45 mm⁻¹
α = 77.86 (3)°	T = 298 K
β = 81.28 (3)°	Block, yellow
γ = 83.18 (3)°	0.30 × 0.10 × 0.10 mm
V = 750.4 (3) Å³

Data collection top

Bruker SMART APEX area-detector diffractometer	2945 independent reflections
Radiation source: fine-focus sealed tube	1683 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = 0→9
T_min = 0.945, T_max = 0.954	k = −10→10
3184 measured reflections	l = −14→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0586P)²] where P = (F_o² + 2F_c²)/3
2945 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	1.00102 (16)	0.96288 (12)	0.16086 (12)	0.0699 (4)
C1	0.3620 (5)	0.7496 (4)	0.3585 (3)	0.0371 (9)
N1	0.2534 (6)	0.3292 (5)	0.4793 (4)	0.0614 (11)
O1	0.2981 (6)	0.2726 (4)	0.3963 (4)	0.1026 (15)
Cl2	1.10412 (17)	1.57249 (13)	0.15348 (10)	0.0624 (4)
C2	0.3452 (5)	0.5872 (5)	0.3696 (3)	0.0418 (10)
H2	0.3870	0.5357	0.3096	0.050*
O2	0.1969 (6)	0.2536 (4)	0.5713 (3)	0.0927 (13)
O3	0.4612 (4)	0.7781 (3)	0.1658 (2)	0.0485 (7)
C3	0.2664 (6)	0.5033 (5)	0.4695 (4)	0.0465 (11)
O4	0.4518 (4)	1.1466 (3)	0.0730 (3)	0.0502 (8)
C4	0.2019 (6)	0.5719 (6)	0.5597 (4)	0.0612 (13)
H4	0.1487	0.5117	0.6265	0.073*
C5	0.2180 (7)	0.7337 (6)	0.5492 (4)	0.0748 (16)
H5	0.1743	0.7839	0.6096	0.090*
C6	0.2985 (6)	0.8221 (5)	0.4497 (4)	0.0589 (13)
H6A	0.3100	0.9308	0.4440	0.071*
C7	0.4509 (5)	0.8379 (4)	0.2483 (3)	0.0376 (9)
C8	0.5300 (6)	0.9914 (4)	0.2458 (3)	0.0424 (10)
H7A	0.6271	0.9688	0.2929	0.051*
H7B	0.4362	1.0634	0.2782	0.051*
C9	0.6060 (5)	1.0772 (4)	0.1287 (3)	0.0389 (9)
H9	0.6755	0.9978	0.0878	0.047*
C10	0.7296 (5)	1.2019 (4)	0.1350 (3)	0.0358 (9)
C11	0.9118 (5)	1.1633 (4)	0.1489 (3)	0.0410 (10)
C12	1.0294 (6)	1.2732 (5)	0.1532 (3)	0.0437 (10)
H12	1.1518	1.2425	0.1603	0.052*
C13	0.9586 (6)	1.4313 (4)	0.1465 (3)	0.0421 (10)
C14	0.7802 (6)	1.4755 (5)	0.1344 (4)	0.0479 (11)
H14	0.7346	1.5825	0.1300	0.058*
C15	0.6660 (6)	1.3617 (5)	0.1286 (3)	0.0439 (10)
H15	0.5442	1.3934	0.1203	0.053*
H10	0.492 (7)	1.164 (6)	−0.007 (4)	0.085 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0546 (8)	0.0320 (6)	0.1198 (12)	0.0098 (5)	−0.0181 (7)	−0.0106 (6)
C1	0.034 (2)	0.043 (2)	0.036 (2)	−0.0048 (17)	−0.0016 (18)	−0.0107 (18)
N1	0.059 (3)	0.051 (2)	0.068 (3)	−0.009 (2)	−0.009 (2)	0.007 (2)
O1	0.144 (4)	0.049 (2)	0.105 (3)	−0.019 (2)	0.022 (3)	−0.015 (2)
Cl2	0.0758 (9)	0.0482 (7)	0.0684 (8)	−0.0218 (6)	−0.0052 (7)	−0.0172 (6)
C2	0.041 (2)	0.042 (2)	0.040 (2)	−0.0014 (19)	−0.007 (2)	−0.0043 (19)
O2	0.112 (3)	0.069 (2)	0.080 (3)	−0.025 (2)	−0.007 (2)	0.029 (2)
O3	0.0623 (19)	0.0437 (16)	0.0387 (17)	−0.0063 (14)	0.0011 (15)	−0.0110 (13)
C3	0.042 (3)	0.050 (2)	0.044 (3)	−0.010 (2)	−0.008 (2)	0.002 (2)
O4	0.0422 (18)	0.0621 (19)	0.0452 (19)	−0.0026 (14)	−0.0089 (15)	−0.0071 (15)
C4	0.065 (3)	0.076 (3)	0.041 (3)	−0.031 (3)	0.000 (2)	0.001 (2)
C5	0.097 (4)	0.084 (4)	0.048 (3)	−0.035 (3)	0.019 (3)	−0.026 (3)
C6	0.066 (3)	0.054 (3)	0.056 (3)	−0.020 (2)	0.008 (3)	−0.013 (2)
C7	0.034 (2)	0.037 (2)	0.041 (2)	0.0011 (17)	−0.0052 (19)	−0.0076 (19)
C8	0.045 (2)	0.042 (2)	0.040 (2)	−0.0062 (19)	−0.003 (2)	−0.0054 (18)
C9	0.040 (2)	0.040 (2)	0.035 (2)	−0.0025 (18)	−0.0020 (19)	−0.0081 (18)
C10	0.035 (2)	0.036 (2)	0.033 (2)	−0.0013 (17)	−0.0029 (18)	−0.0034 (17)
C11	0.045 (2)	0.0251 (19)	0.049 (3)	0.0042 (17)	−0.005 (2)	−0.0035 (17)
C12	0.039 (2)	0.042 (2)	0.050 (3)	−0.0032 (19)	−0.006 (2)	−0.0075 (19)
C13	0.050 (3)	0.035 (2)	0.040 (2)	−0.0073 (19)	0.002 (2)	−0.0079 (18)
C14	0.056 (3)	0.031 (2)	0.052 (3)	0.006 (2)	0.000 (2)	−0.0091 (19)
C15	0.036 (2)	0.043 (2)	0.049 (3)	0.0049 (19)	0.001 (2)	−0.0095 (19)

Geometric parameters (Å, º) top

Cl1—C11	1.746 (4)	C5—H5	0.9300
C1—C6	1.384 (5)	C6—H6A	0.9300
C1—C2	1.385 (5)	C7—C8	1.493 (5)
C1—C7	1.500 (5)	C8—C9	1.525 (5)
N1—O1	1.203 (5)	C8—H7A	0.9700
N1—O2	1.217 (5)	C8—H7B	0.9700
N1—C3	1.481 (6)	C9—C10	1.509 (5)
Cl2—C13	1.738 (4)	C9—H9	0.9800
C2—C3	1.368 (5)	C10—C15	1.381 (5)
C2—H2	0.9300	C10—C11	1.385 (5)
O3—C7	1.215 (4)	C11—C12	1.371 (5)
C3—C4	1.357 (6)	C12—C13	1.381 (5)
O4—C9	1.429 (5)	C12—H12	0.9300
O4—H10	0.97 (5)	C13—C14	1.359 (6)
C4—C5	1.379 (6)	C14—C15	1.384 (5)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.384 (6)	C15—H15	0.9300

C6—C1—C2	118.7 (4)	C7—C8—H7B	108.6
C6—C1—C7	123.2 (4)	C9—C8—H7B	108.6
C2—C1—C7	118.1 (3)	H7A—C8—H7B	107.6
O1—N1—O2	124.6 (5)	O4—C9—C10	112.0 (3)
O1—N1—C3	118.1 (4)	O4—C9—C8	106.3 (3)
O2—N1—C3	117.3 (5)	C10—C9—C8	111.4 (3)
C3—C2—C1	119.3 (4)	O4—C9—H9	109.0
C3—C2—H2	120.3	C10—C9—H9	109.0
C1—C2—H2	120.3	C8—C9—H9	109.0
C4—C3—C2	123.1 (4)	C15—C10—C11	116.1 (4)
C4—C3—N1	118.9 (4)	C15—C10—C9	121.6 (4)
C2—C3—N1	118.1 (4)	C11—C10—C9	122.3 (3)
C9—O4—H10	107 (3)	C12—C11—C10	124.2 (3)
C3—C4—C5	117.9 (4)	C12—C11—Cl1	117.0 (3)
C3—C4—H4	121.1	C10—C11—Cl1	118.8 (3)
C5—C4—H4	121.1	C11—C12—C13	117.3 (4)
C4—C5—C6	120.6 (5)	C11—C12—H12	121.3
C4—C5—H5	119.7	C13—C12—H12	121.3
C6—C5—H5	119.7	C14—C13—C12	121.0 (4)
C1—C6—C5	120.4 (4)	C14—C13—Cl2	120.8 (3)
C1—C6—H6A	119.8	C12—C13—Cl2	118.2 (3)
C5—C6—H6A	119.8	C13—C14—C15	120.2 (4)
O3—C7—C8	122.8 (4)	C13—C14—H14	119.9
O3—C7—C1	118.4 (3)	C15—C14—H14	119.9
C8—C7—C1	118.7 (3)	C10—C15—C14	121.3 (4)
C7—C8—C9	114.6 (3)	C10—C15—H15	119.4
C7—C8—H7A	108.6	C14—C15—H15	119.4
C9—C8—H7A	108.6

C6—C1—C2—C3	0.1 (6)	C7—C8—C9—O4	74.1 (4)
C7—C1—C2—C3	179.3 (4)	C7—C8—C9—C10	−163.6 (3)
C1—C2—C3—C4	0.3 (6)	O4—C9—C10—C15	23.3 (5)
C1—C2—C3—N1	−178.9 (4)	C8—C9—C10—C15	−95.7 (4)
O1—N1—C3—C4	174.4 (5)	O4—C9—C10—C11	−157.6 (4)
O2—N1—C3—C4	−5.2 (6)	C8—C9—C10—C11	83.4 (5)
O1—N1—C3—C2	−6.3 (6)	C15—C10—C11—C12	−2.0 (6)
O2—N1—C3—C2	174.1 (4)	C9—C10—C11—C12	178.9 (4)
C2—C3—C4—C5	−0.2 (7)	C15—C10—C11—Cl1	178.6 (3)
N1—C3—C4—C5	179.0 (4)	C9—C10—C11—Cl1	−0.5 (5)
C3—C4—C5—C6	−0.4 (8)	C10—C11—C12—C13	2.1 (6)
C2—C1—C6—C5	−0.7 (7)	Cl1—C11—C12—C13	−178.5 (3)
C7—C1—C6—C5	−179.9 (4)	C11—C12—C13—C14	−1.0 (6)
C4—C5—C6—C1	0.9 (8)	C11—C12—C13—Cl2	179.2 (3)
C6—C1—C7—O3	−162.1 (4)	C12—C13—C14—C15	0.0 (6)
C2—C1—C7—O3	18.8 (5)	Cl2—C13—C14—C15	179.8 (3)
C6—C1—C7—C8	20.7 (6)	C11—C10—C15—C14	0.9 (6)
C2—C1—C7—C8	−158.5 (4)	C9—C10—C15—C14	−180.0 (4)
O3—C7—C8—C9	6.6 (6)	C13—C14—C15—C10	0.0 (6)
C1—C7—C8—C9	−176.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H10···O3ⁱ	0.97 (5)	1.89 (5)	2.852 (4)	171 (4)
C8—H7B···O1ⁱⁱ	0.97	2.56	3.474 (4)	157
C9—H9···Cl1	0.98	2.67	3.042 (4)	103
C12—H12···O4ⁱⁱⁱ	0.93	2.45	3.275 (4)	148
C14—H14···O3ⁱⁱ	0.93	2.52	3.340 (4)	147
C15—H15···O4	0.93	2.50	2.816 (4)	100

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

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3-(2,4-Dichloro­phen­yl)-3-hydr­oxy-1-(3-nitro­phen­yl)propan-1-one

Supporting information

Key indicators

checkCIF/PLATON results

3-(2,4-Dichlorophenyl)-3-hydroxy-1-(3-nitrophenyl)propan-1-one