3-(3-Bromo­phenyl)-1-(2-naphthyl)prop-2-en-1-one

The title mol­ecule, C₁₉H₁₃BrO, has an s–cis conformation for the ketone system. The dihedral angle between the benzene and naphthalene ring systems is 50.14 (3)°. C—H...Br inter­actions link the mol­ecules into chains along the c axis, which are inter­linked via C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.035
• wR factor = 0.096
• Data-to-parameter ratio = 32.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.45
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          5

   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

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

3-(3-Bromophenyl)-1-(2-naphthyl)prop-2-en-1-one

Crystal data

C19H13BrO	Z = 2
Mr = 337.20	F(000) = 340
Triclinic, P1	Dx = 1.573 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8213 (1) Å	Cell parameters from 9858 reflections
b = 7.3549 (1) Å	θ = 2.5–38.5°
c = 16.7023 (3) Å	µ = 2.88 mm^−1
α = 88.199 (1)°	T = 100 K
β = 84.947 (1)°	Block, colourless
γ = 89.454 (1)°	0.59 × 0.56 × 0.22 mm
V = 711.96 (2) Å^3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	6221 independent reflections
Radiation source: fine-focus sealed tube	5288 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.33 pixels mm^-1	θmax = 35.0°, θmin = 2.5°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.213, Tmax = 0.530	l = −26→26
19651 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0464P)^2 + 0.4791P] where P = (Fo^2 + 2Fc^2)/3
6221 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 1.60 e Å^−3
0 restraints	Δρmin = −0.66 e Å^−3

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	0.32327 (3)	0.21895 (2)	0.036827 (9)	0.02761 (6)
O1	−0.1809 (2)	0.20065 (18)	0.48047 (7)	0.0235 (2)
C1	0.2705 (2)	0.20723 (19)	0.20738 (9)	0.0169 (2)
H1	0.1239	0.2604	0.2005	0.020*
C2	0.4196 (3)	0.1670 (2)	0.14082 (9)	0.0182 (2)
C3	0.6354 (3)	0.0891 (2)	0.14822 (9)	0.0197 (2)
H3	0.7354	0.0621	0.1020	0.024*
C4	0.7007 (2)	0.0518 (2)	0.22507 (10)	0.0197 (2)
H4	0.8475	−0.0016	0.2313	0.024*
C5	0.5555 (2)	0.0911 (2)	0.29297 (9)	0.0182 (2)
H5	0.6039	0.0654	0.3450	0.022*
C6	0.3367 (2)	0.16913 (19)	0.28468 (8)	0.0159 (2)
C7	0.1704 (2)	0.20522 (19)	0.35338 (9)	0.0168 (2)
H7	0.0174	0.2349	0.3417	0.020*
C8	0.2123 (3)	0.2006 (2)	0.43108 (9)	0.0187 (2)
H8	0.3645	0.1798	0.4458	0.022*
C9	0.0194 (2)	0.2282 (2)	0.49414 (9)	0.0177 (2)
C10	0.0766 (2)	0.28719 (19)	0.57450 (9)	0.0167 (2)
C11	0.2910 (2)	0.3686 (2)	0.58550 (9)	0.0188 (2)
H11	0.4042	0.3827	0.5412	0.023*
C12	0.3357 (2)	0.4270 (2)	0.65950 (9)	0.0185 (2)
H12	0.4774	0.4860	0.6655	0.022*
C13	0.1739 (2)	0.40087 (19)	0.72726 (9)	0.0168 (2)
C14	0.2207 (3)	0.4521 (2)	0.80543 (9)	0.0197 (2)
H14	0.3618	0.5103	0.8130	0.024*
C15	0.0637 (3)	0.4180 (2)	0.86994 (9)	0.0216 (3)
H15	0.0971	0.4530	0.9219	0.026*
C16	−0.1478 (3)	0.3314 (2)	0.86031 (9)	0.0215 (3)
H16	−0.2540	0.3069	0.9058	0.026*
C17	−0.1995 (3)	0.2829 (2)	0.78545 (9)	0.0185 (2)
H17	−0.3427	0.2265	0.7792	0.022*
C18	−0.0403 (2)	0.31621 (19)	0.71694 (8)	0.0160 (2)
C19	−0.0855 (2)	0.26354 (19)	0.63929 (9)	0.0166 (2)
H19	−0.2300	0.2109	0.6315	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.03378 (10)	0.03447 (10)	0.01432 (7)	0.01017 (6)	−0.00159 (5)	−0.00144 (6)
O1	0.0187 (5)	0.0311 (6)	0.0207 (5)	−0.0026 (4)	−0.0018 (4)	−0.0003 (4)
C1	0.0163 (5)	0.0178 (6)	0.0163 (5)	0.0007 (4)	−0.0003 (4)	0.0000 (4)
C2	0.0200 (6)	0.0186 (6)	0.0161 (6)	0.0006 (4)	−0.0011 (4)	−0.0009 (4)
C3	0.0180 (6)	0.0183 (6)	0.0221 (6)	0.0010 (4)	0.0018 (5)	−0.0017 (5)
C4	0.0155 (5)	0.0177 (6)	0.0256 (7)	0.0005 (4)	−0.0007 (5)	−0.0004 (5)
C5	0.0172 (6)	0.0180 (6)	0.0195 (6)	0.0007 (4)	−0.0025 (4)	−0.0001 (5)
C6	0.0160 (5)	0.0156 (5)	0.0162 (5)	−0.0009 (4)	−0.0012 (4)	−0.0001 (4)
C7	0.0167 (5)	0.0169 (5)	0.0164 (5)	−0.0008 (4)	0.0002 (4)	−0.0005 (4)
C8	0.0183 (6)	0.0205 (6)	0.0169 (6)	0.0003 (5)	−0.0004 (4)	−0.0001 (5)
C9	0.0184 (6)	0.0179 (6)	0.0165 (6)	−0.0006 (4)	−0.0001 (4)	0.0022 (4)
C10	0.0163 (5)	0.0172 (6)	0.0164 (5)	−0.0006 (4)	−0.0001 (4)	0.0004 (4)
C11	0.0170 (6)	0.0195 (6)	0.0191 (6)	−0.0023 (4)	0.0016 (4)	0.0001 (5)
C12	0.0160 (5)	0.0179 (6)	0.0212 (6)	−0.0029 (4)	−0.0002 (4)	−0.0008 (5)
C13	0.0160 (5)	0.0149 (5)	0.0194 (6)	0.0006 (4)	−0.0013 (4)	−0.0014 (4)
C14	0.0198 (6)	0.0190 (6)	0.0207 (6)	0.0028 (5)	−0.0041 (5)	−0.0031 (5)
C15	0.0256 (7)	0.0227 (6)	0.0168 (6)	0.0046 (5)	−0.0033 (5)	−0.0022 (5)
C16	0.0235 (6)	0.0235 (7)	0.0170 (6)	0.0023 (5)	0.0016 (5)	−0.0003 (5)
C17	0.0181 (6)	0.0189 (6)	0.0179 (6)	0.0005 (4)	0.0018 (4)	0.0003 (5)
C18	0.0155 (5)	0.0157 (5)	0.0164 (5)	0.0014 (4)	−0.0003 (4)	0.0002 (4)
C19	0.0151 (5)	0.0164 (5)	0.0181 (6)	−0.0006 (4)	0.0000 (4)	0.0011 (4)

Geometric parameters (Å, º)

Br1—C2	1.8982 (15)	C10—C19	1.379 (2)
O1—C9	1.2280 (19)	C10—C11	1.418 (2)
C1—C2	1.386 (2)	C11—C12	1.368 (2)
C1—C6	1.399 (2)	C11—H11	0.95
C1—H1	0.95	C12—C13	1.417 (2)
C2—C3	1.390 (2)	C12—H12	0.95
C3—C4	1.389 (2)	C13—C14	1.420 (2)
C3—H3	0.95	C13—C18	1.426 (2)
C4—C5	1.389 (2)	C14—C15	1.369 (2)
C4—H4	0.95	C14—H14	0.95
C5—C6	1.4082 (19)	C15—C16	1.415 (2)
C5—H5	0.95	C15—H15	0.95
C6—C7	1.464 (2)	C16—C17	1.370 (2)
C7—C8	1.341 (2)	C16—H16	0.95
C7—H7	0.95	C17—C18	1.424 (2)
C8—C9	1.487 (2)	C17—H17	0.95
C8—H8	0.95	C18—C19	1.412 (2)
C9—C10	1.489 (2)	C19—H19	0.95
C2—C1—C6	119.75 (13)	C11—C10—C9	121.68 (13)
C2—C1—H1	120.1	C12—C11—C10	120.39 (13)
C6—C1—H1	120.1	C12—C11—H11	119.8
C1—C2—C3	121.95 (13)	C10—C11—H11	119.8
C1—C2—Br1	118.63 (11)	C11—C12—C13	120.99 (13)
C3—C2—Br1	119.42 (11)	C11—C12—H12	119.5
C4—C3—C2	118.11 (13)	C13—C12—H12	119.5
C4—C3—H3	120.9	C12—C13—C14	122.11 (13)
C2—C3—H3	120.9	C12—C13—C18	118.90 (13)
C3—C4—C5	121.32 (13)	C14—C13—C18	118.98 (13)
C3—C4—H4	119.3	C15—C14—C13	120.36 (14)
C5—C4—H4	119.3	C15—C14—H14	119.8
C4—C5—C6	120.03 (13)	C13—C14—H14	119.8
C4—C5—H5	120.0	C14—C15—C16	120.95 (15)
C6—C5—H5	120.0	C14—C15—H15	119.5
C1—C6—C5	118.83 (13)	C16—C15—H15	119.5
C1—C6—C7	118.18 (12)	C17—C16—C15	120.05 (14)
C5—C6—C7	122.94 (13)	C17—C16—H16	120.0
C8—C7—C6	126.53 (13)	C15—C16—H16	120.0
C8—C7—H7	116.7	C16—C17—C18	120.58 (14)
C6—C7—H7	116.7	C16—C17—H17	119.7
C7—C8—C9	119.71 (13)	C18—C17—H17	119.7
C7—C8—H8	120.1	C19—C18—C17	122.02 (13)
C9—C8—H8	120.1	C19—C18—C13	118.89 (13)
O1—C9—C8	120.76 (14)	C17—C18—C13	119.07 (13)
O1—C9—C10	121.07 (13)	C10—C19—C18	121.14 (13)
C8—C9—C10	118.16 (13)	C10—C19—H19	119.4
C19—C10—C11	119.63 (13)	C18—C19—H19	119.4
C19—C10—C9	118.69 (13)
C6—C1—C2—C3	0.0 (2)	C9—C10—C11—C12	177.81 (13)
C6—C1—C2—Br1	179.55 (11)	C10—C11—C12—C13	2.7 (2)
C1—C2—C3—C4	−0.2 (2)	C11—C12—C13—C14	176.84 (14)
Br1—C2—C3—C4	−179.68 (11)	C11—C12—C13—C18	−1.5 (2)
C2—C3—C4—C5	−0.1 (2)	C12—C13—C14—C15	−177.40 (14)
C3—C4—C5—C6	0.5 (2)	C18—C13—C14—C15	1.0 (2)
C2—C1—C6—C5	0.3 (2)	C13—C14—C15—C16	0.0 (2)
C2—C1—C6—C7	−177.07 (13)	C14—C15—C16—C17	−1.0 (2)
C4—C5—C6—C1	−0.6 (2)	C15—C16—C17—C18	1.0 (2)
C4—C5—C6—C7	176.70 (14)	C16—C17—C18—C19	178.27 (13)
C1—C6—C7—C8	−170.46 (15)	C16—C17—C18—C13	0.0 (2)
C5—C6—C7—C8	12.3 (2)	C12—C13—C18—C19	−0.87 (19)
C6—C7—C8—C9	−175.73 (13)	C14—C13—C18—C19	−179.31 (13)
C7—C8—C9—O1	22.2 (2)	C12—C13—C18—C17	177.45 (13)
C7—C8—C9—C10	−158.74 (14)	C14—C13—C18—C17	−0.99 (19)
O1—C9—C10—C19	17.5 (2)	C11—C10—C19—C18	−1.1 (2)
C8—C9—C10—C19	−161.61 (13)	C9—C10—C19—C18	179.71 (12)
O1—C9—C10—C11	−161.71 (14)	C17—C18—C19—C10	−176.08 (13)
C8—C9—C10—C11	19.2 (2)	C13—C18—C19—C10	2.2 (2)
C19—C10—C11—C12	−1.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Br1^i	0.95	2.93	3.5552 (16)	125
C1—H1···Cg1^ii	0.95	2.85	3.5236 (15)	129
C4—H4···Cg1^iii	0.95	2.84	3.5012 (15)	128
C14—H14···Cg2^iv	0.95	2.82	3.5274 (17)	132
C17—H17···Cg2^v	0.95	2.75	3.4772 (17)	134

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