7-Bromo-1-methyl­sulfanyl-2-phenyl­naphtho[2,1-b]furan

The title compound, C₁₉H₁₃BrOS, was prepared by the Lewis acid-catalysed reaction of 6-bromo-2-naphthol with 2-chloro-2-(methyl­sulfan­yl)acetophenone. The naphthofuran ring system is nearly planar. The crystal structure is stabilized by a C—H...π inter­action.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.020
• wR factor = 0.048
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C19 H13 Br O S

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.00
           From the CIF: _reflns_number_total               2856
           Count of symmetry unique reflns         1684
           Completeness (_total/calc)            169.60%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1172
           Fraction of Friedel pairs measured     0.696
           Are heavy atom types Z>Si present        yes

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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 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: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

7-Bromo-1-methylsulfanyl-2-phenylnaphtho[2,1-b]furan

Crystal data

C19H13BrOS	F(000) = 744
Mr = 369.26	Dx = 1.653 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2c -2ac	Cell parameters from 6032 reflections
a = 17.700 (1) Å	θ = 2.3–28.3°
b = 5.2952 (3) Å	µ = 2.91 mm^−1
c = 15.8343 (9) Å	T = 173 K
V = 1484.07 (15) Å^3	Plate, pale yellow
Z = 4	0.35 × 0.20 × 0.02 mm

Data collection

Bruker SMART CCD diffractometer	2856 independent reflections
Radiation source: fine-focus sealed tube	2689 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 10.00 pixels mm^-1	θmax = 27.0°, θmin = 2.3°
φ and ω scans	h = −21→22
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −6→6
Tmin = 0.512, Tmax = 0.951	l = −20→18
7803 measured reflections

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)] = 0.020	H-atom parameters constrained
wR(F^2) = 0.048	w = 1/[σ^2(Fo^2) + (0.0244P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2856 reflections	Δρmax = 0.24 e Å^−3
199 parameters	Δρmin = −0.33 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1198 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.013 (6)

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
Br	0.334364 (9)	0.11436 (3)	−0.005089 (17)	0.02683 (6)
S	0.04310 (3)	−0.90073 (8)	0.06038 (3)	0.02203 (10)
O	0.05073 (8)	−0.6924 (3)	0.30060 (8)	0.0219 (3)
C1	0.26552 (10)	−0.0990 (3)	0.05389 (14)	0.0215 (4)
C2	0.25353 (10)	−0.0651 (4)	0.13774 (13)	0.0216 (4)
H2	0.2789	0.0623	0.1666	0.026*
C3	0.20211 (10)	−0.2247 (4)	0.18142 (11)	0.0196 (4)
C4	0.18858 (11)	−0.1912 (4)	0.26962 (12)	0.0227 (4)
H4	0.2137	−0.0626	0.2981	0.027*
C5	0.14009 (11)	−0.3418 (4)	0.31314 (12)	0.0239 (4)
H5	0.1319	−0.3214	0.3707	0.029*
C6	0.10303 (11)	−0.5302 (4)	0.26626 (13)	0.0197 (4)
C7	0.11208 (11)	−0.5717 (4)	0.18168 (12)	0.0192 (4)
C8	0.16363 (9)	−0.4184 (4)	0.13526 (14)	0.0182 (4)
C9	0.17945 (11)	−0.4473 (4)	0.04850 (13)	0.0217 (4)
H9	0.1557	−0.5752	0.0182	0.026*
C10	0.22939 (10)	−0.2895 (4)	0.00796 (12)	0.0224 (4)
H10	0.2390	−0.3093	−0.0494	0.027*
C11	0.05930 (10)	−0.7713 (3)	0.16093 (11)	0.0187 (4)
C12	0.02427 (10)	−0.8369 (4)	0.23456 (12)	0.0198 (4)
C13	−0.03587 (11)	−1.0146 (4)	0.25809 (13)	0.0202 (4)
C14	−0.07671 (11)	−0.9756 (4)	0.33207 (13)	0.0236 (4)
H14	−0.0650	−0.8396	0.3668	0.028*
C15	−0.13494 (12)	−1.1387 (4)	0.35426 (14)	0.0275 (4)
H15	−0.1622	−1.1109	0.4036	0.033*
C16	−0.15242 (12)	−1.3418 (4)	0.30329 (15)	0.0279 (5)
H16	−0.1913	−1.4509	0.3186	0.034*
C17	−0.11260 (13)	−1.3841 (4)	0.22971 (16)	0.0283 (5)
H17	−0.1250	−1.5203	0.1953	0.034*
C18	−0.05374 (11)	−1.2227 (4)	0.20679 (13)	0.0233 (4)
H18	−0.0264	−1.2528	0.1577	0.028*
C19	−0.00702 (12)	−0.6429 (4)	0.01092 (13)	0.0294 (5)
H19A	−0.0201	−0.6888	−0.0459	0.044*
H19B	0.0246	−0.4956	0.0101	0.044*
H19C	−0.0522	−0.6074	0.0422	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br	0.02390 (9)	0.02577 (10)	0.03084 (10)	−0.00367 (7)	0.00563 (9)	−0.00068 (10)
S	0.0270 (2)	0.0203 (2)	0.0189 (2)	−0.00209 (17)	−0.00106 (19)	−0.00438 (17)
O	0.0208 (7)	0.0265 (7)	0.0182 (6)	−0.0025 (6)	0.0008 (5)	−0.0006 (6)
C1	0.0159 (8)	0.0204 (9)	0.0282 (9)	0.0006 (6)	0.0026 (8)	0.0023 (7)
C2	0.0181 (9)	0.0218 (10)	0.0247 (9)	−0.0002 (7)	−0.0037 (8)	−0.0049 (8)
C3	0.0155 (8)	0.0228 (9)	0.0206 (9)	0.0011 (7)	−0.0040 (7)	−0.0024 (7)
C4	0.0203 (9)	0.0268 (10)	0.0208 (9)	−0.0014 (8)	−0.0066 (8)	−0.0054 (8)
C5	0.0216 (9)	0.0338 (11)	0.0165 (9)	0.0012 (8)	−0.0029 (8)	−0.0047 (8)
C6	0.0153 (8)	0.0242 (10)	0.0196 (9)	0.0018 (8)	0.0005 (7)	0.0005 (8)
C7	0.0160 (8)	0.0204 (8)	0.0212 (9)	0.0029 (8)	−0.0035 (7)	−0.0017 (7)
C8	0.0162 (9)	0.0197 (10)	0.0188 (9)	0.0034 (6)	−0.0009 (7)	−0.0021 (7)
C9	0.0208 (8)	0.0224 (9)	0.0219 (10)	−0.0001 (7)	0.0007 (8)	−0.0065 (8)
C10	0.0219 (8)	0.0265 (9)	0.0188 (10)	0.0000 (7)	0.0035 (7)	−0.0035 (7)
C11	0.0177 (8)	0.0196 (9)	0.0189 (9)	0.0016 (7)	−0.0029 (7)	−0.0022 (7)
C12	0.0166 (8)	0.0216 (9)	0.0212 (9)	0.0027 (7)	−0.0017 (7)	−0.0016 (7)
C13	0.0184 (8)	0.0200 (10)	0.0221 (9)	0.0035 (7)	−0.0015 (7)	0.0057 (7)
C14	0.0252 (10)	0.0245 (10)	0.0210 (9)	0.0008 (8)	−0.0015 (8)	0.0041 (7)
C15	0.0243 (10)	0.0333 (12)	0.0248 (10)	0.0025 (8)	0.0052 (8)	0.0104 (9)
C16	0.0223 (10)	0.0272 (11)	0.0342 (11)	−0.0036 (8)	−0.0024 (9)	0.0134 (9)
C17	0.0289 (11)	0.0198 (11)	0.0362 (12)	−0.0003 (8)	−0.0039 (9)	0.0047 (9)
C18	0.0225 (10)	0.0210 (10)	0.0262 (10)	0.0034 (8)	0.0011 (8)	0.0015 (8)
C19	0.0328 (10)	0.0318 (12)	0.0235 (11)	0.0013 (8)	−0.0056 (8)	−0.0006 (8)

Geometric parameters (Å, º)

C1—Br	1.9061 (19)	C9—C10	1.375 (3)
S—C11	1.7569 (19)	C9—H9	0.9300
S—C19	1.807 (2)	C10—H10	0.9300
O—C6	1.375 (2)	C11—C12	1.365 (3)
O—C12	1.378 (2)	C12—C13	1.469 (3)
C1—C2	1.357 (3)	C13—C14	1.392 (3)
C1—C10	1.399 (3)	C13—C18	1.405 (3)
C2—C3	1.422 (3)	C14—C15	1.390 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.428 (3)	C15—C16	1.380 (3)
C3—C8	1.432 (3)	C15—H15	0.9300
C4—C5	1.359 (3)	C16—C17	1.380 (4)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.406 (3)	C17—C18	1.395 (3)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.367 (3)	C18—H18	0.9300
C7—C8	1.426 (3)	C19—H19A	0.9600
C7—C11	1.448 (3)	C19—H19B	0.9600
C8—C9	1.410 (3)	C19—H19C	0.9600
C11—S—C19	100.27 (9)	C1—C10—H10	120.3
C6—O—C12	106.00 (15)	C12—C11—C7	106.55 (16)
C2—C1—C10	122.20 (18)	C12—C11—S	126.90 (15)
C2—C1—Br	120.07 (15)	C7—C11—S	126.55 (14)
C10—C1—Br	117.72 (16)	C11—C12—O	110.63 (16)
C1—C2—C3	119.84 (17)	C11—C12—C13	135.13 (18)
C1—C2—H2	120.1	O—C12—C13	114.18 (16)
C3—C2—H2	120.1	C14—C13—C18	119.09 (18)
C2—C3—C4	120.62 (17)	C14—C13—C12	119.65 (18)
C2—C3—C8	118.82 (17)	C18—C13—C12	121.25 (18)
C4—C3—C8	120.55 (18)	C15—C14—C13	120.4 (2)
C5—C4—C3	121.94 (18)	C15—C14—H14	119.8
C5—C4—H4	119.0	C13—C14—H14	119.8
C3—C4—H4	119.0	C16—C15—C14	120.2 (2)
C4—C5—C6	116.31 (18)	C16—C15—H15	119.9
C4—C5—H5	121.8	C14—C15—H15	119.9
C6—C5—H5	121.8	C15—C16—C17	120.4 (2)
C7—C6—O	111.46 (18)	C15—C16—H16	119.8
C7—C6—C5	125.25 (19)	C17—C16—H16	119.8
O—C6—C5	123.27 (18)	C16—C17—C18	120.1 (2)
C6—C7—C8	119.25 (18)	C16—C17—H17	119.9
C6—C7—C11	105.32 (17)	C18—C17—H17	119.9
C8—C7—C11	135.36 (18)	C17—C18—C13	119.9 (2)
C9—C8—C7	124.57 (18)	C17—C18—H18	120.1
C9—C8—C3	118.72 (17)	C13—C18—H18	120.1
C7—C8—C3	116.70 (18)	S—C19—H19A	109.5
C10—C9—C8	121.08 (18)	S—C19—H19B	109.5
C10—C9—H9	119.5	H19A—C19—H19B	109.5
C8—C9—H9	119.5	S—C19—H19C	109.5
C9—C10—C1	119.31 (17)	H19A—C19—H19C	109.5
C9—C10—H10	120.3	H19B—C19—H19C	109.5
C10—C1—C2—C3	−0.7 (3)	C2—C1—C10—C9	0.6 (3)
Br—C1—C2—C3	179.98 (13)	Br—C1—C10—C9	179.88 (15)
C1—C2—C3—C4	−179.78 (18)	C6—C7—C11—C12	−1.3 (2)
C1—C2—C3—C8	−0.3 (3)	C8—C7—C11—C12	−178.0 (2)
C2—C3—C4—C5	−179.60 (18)	C6—C7—C11—S	178.11 (15)
C8—C3—C4—C5	0.9 (3)	C8—C7—C11—S	1.4 (3)
C3—C4—C5—C6	−1.0 (3)	C19—S—C11—C12	107.17 (19)
C12—O—C6—C7	−1.7 (2)	C19—S—C11—C7	−72.15 (17)
C12—O—C6—C5	176.52 (18)	C7—C11—C12—O	0.3 (2)
C4—C5—C6—C7	0.0 (3)	S—C11—C12—O	−179.13 (13)
C4—C5—C6—O	−178.03 (18)	C7—C11—C12—C13	177.3 (2)
O—C6—C7—C8	179.26 (16)	S—C11—C12—C13	−2.1 (3)
C5—C6—C7—C8	1.1 (3)	C6—O—C12—C11	0.8 (2)
O—C6—C7—C11	1.9 (2)	C6—O—C12—C13	−176.84 (16)
C5—C6—C7—C11	−176.31 (19)	C11—C12—C13—C14	−157.4 (2)
C6—C7—C8—C9	178.14 (18)	O—C12—C13—C14	19.5 (3)
C11—C7—C8—C9	−5.5 (3)	C11—C12—C13—C18	21.9 (3)
C6—C7—C8—C3	−1.0 (3)	O—C12—C13—C18	−161.23 (17)
C11—C7—C8—C3	175.3 (2)	C18—C13—C14—C15	−0.8 (3)
C2—C3—C8—C9	1.4 (3)	C12—C13—C14—C15	178.52 (17)
C4—C3—C8—C9	−179.11 (17)	C13—C14—C15—C16	0.4 (3)
C2—C3—C8—C7	−179.37 (16)	C14—C15—C16—C17	−0.4 (3)
C4—C3—C8—C7	0.1 (3)	C15—C16—C17—C18	0.7 (3)
C7—C8—C9—C10	179.25 (18)	C16—C17—C18—C13	−1.0 (3)
C3—C8—C9—C10	−1.6 (3)	C14—C13—C18—C17	1.1 (3)
C8—C9—C10—C1	0.6 (3)	C12—C13—C18—C17	−178.21 (18)