exo-7-Phenyl-3-n-propyl-5-oxa-2-thia-6-aza­bi­cyclo­[3.2.0^1,4]­hept-6-ene 2,2-dioxide

The title compound, C₁₃H₁₅NO₃, contains the novel exo-thia­bi­cyclo­[3.2.0^1,4]­hept-6-ene ring system, with pendant phenyl and n-propyl substituents. Both fused rings in the bicyclic system are planar, their planes forming a dihedral angle of 65.6 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 130 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.092
• Data-to-parameter ratio = 12.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.90
         From the CIF: _reflns_number_total               2794
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         3007
         Completeness (_total/calc)             92.92%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: SHELXTL (Siemens, 1983); cell refinement: SHELXTL; data reduction: SHELXTL; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 in WinGX (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).

(I)

Crystal data

C13H15NO3S	F(000) = 560
Mr = 265.32	Dx = 1.408 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 24 reflections
a = 12.593 (5) Å	θ = 5.6–14.2°
b = 5.081 (2) Å	µ = 0.26 mm^−1
c = 20.169 (8) Å	T = 130 K
β = 104.028 (15)°	Needle, colourless
V = 1252.0 (9) Å^3	0.44 × 0.19 × 0.04 mm
Z = 4

Data collection

Siemens/Nicolet R3m 4-circle diffractometer	Rint = 0.036
Radiation source: fine-focus sealed tube	θmax = 27.9°, θmin = 2.1°
Graphite monochromator	h = 0→16
ω scans	k = 0→6
2933 measured reflections	l = −26→25
2794 independent reflections	3 standard reflections every 97 reflections
1801 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	All H-atom parameters refined
S = 0.85	w = 1/[σ^2(Fo^2) + (0.0523P)^2] where P = (Fo^2 + 2Fc^2)/3
2794 reflections	(Δ/σ)max < 0.001
223 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.69 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
S2	0.27233 (4)	0.10014 (11)	0.05798 (3)	0.01767 (13)
O21	0.27120 (13)	0.3840 (3)	0.06215 (7)	0.0225 (3)
O22	0.26540 (13)	−0.0206 (3)	−0.00760 (7)	0.0246 (4)
O5	0.31169 (12)	−0.0020 (3)	0.22584 (7)	0.0204 (3)
N6	0.39738 (15)	0.1808 (3)	0.22982 (9)	0.0205 (4)
C1	0.38019 (17)	−0.0420 (4)	0.12644 (10)	0.0179 (4)
C3	0.18686 (17)	−0.0544 (4)	0.10890 (10)	0.0179 (4)
C4	0.29232 (18)	−0.1451 (4)	0.16168 (11)	0.0190 (4)
C7	0.43769 (17)	0.1610 (4)	0.17658 (10)	0.0176 (4)
C8	0.52536 (18)	0.3374 (4)	0.16691 (11)	0.0198 (4)
C9	0.57268 (18)	0.5202 (5)	0.21756 (11)	0.0232 (5)
C10	0.65071 (19)	0.6975 (5)	0.20654 (12)	0.0255 (5)
C11	0.68237 (19)	0.6946 (5)	0.14469 (12)	0.0264 (5)
C12	0.63735 (19)	0.5108 (5)	0.09457 (12)	0.0273 (5)
C13	0.55871 (19)	0.3334 (4)	0.10537 (11)	0.0233 (5)
C14	0.10859 (17)	0.1300 (5)	0.13345 (10)	0.0208 (5)
C15	0.01075 (18)	0.2219 (5)	0.07661 (11)	0.0225 (5)
C16	−0.0624 (2)	0.4135 (6)	0.10292 (13)	0.0278 (5)
H1	0.425 (2)	−0.161 (5)	0.1099 (13)	0.036 (7)*
H3	0.152 (2)	−0.194 (5)	0.0836 (11)	0.024 (6)*
H4	0.292 (2)	−0.329 (5)	0.1713 (12)	0.034 (7)*
H9	0.547 (2)	0.520 (5)	0.2585 (13)	0.037 (7)*
H10	0.681 (2)	0.828 (5)	0.2420 (12)	0.027 (7)*
H11	0.737 (2)	0.821 (5)	0.1348 (13)	0.040 (8)*
H12	0.657 (2)	0.511 (5)	0.0520 (14)	0.042 (8)*
H13	0.527 (2)	0.217 (5)	0.0694 (12)	0.024 (6)*
H14A	0.148 (2)	0.286 (5)	0.1557 (11)	0.023 (6)*
H14B	0.082 (2)	0.031 (5)	0.1682 (13)	0.040 (7)*
H15A	−0.033 (2)	0.066 (5)	0.0564 (12)	0.026 (6)*
H15B	0.038 (2)	0.301 (5)	0.0391 (12)	0.032 (7)*
H16A	−0.027 (3)	0.571 (7)	0.1211 (15)	0.053 (9)*
H16B	−0.119 (3)	0.473 (6)	0.0640 (15)	0.055 (9)*
H16C	−0.096 (2)	0.323 (6)	0.1373 (14)	0.051 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S2	0.0200 (3)	0.0167 (2)	0.0158 (2)	0.0002 (2)	0.00346 (18)	−0.0003 (2)
O21	0.0272 (8)	0.0162 (7)	0.0228 (7)	0.0001 (8)	0.0038 (6)	0.0013 (7)
O22	0.0301 (9)	0.0278 (9)	0.0159 (7)	−0.0037 (7)	0.0060 (6)	−0.0059 (6)
O5	0.0240 (8)	0.0213 (7)	0.0152 (7)	−0.0049 (7)	0.0037 (6)	−0.0007 (6)
N6	0.0196 (9)	0.0192 (9)	0.0221 (9)	−0.0018 (8)	0.0036 (7)	0.0009 (7)
C1	0.0197 (11)	0.0154 (11)	0.0179 (10)	0.0012 (9)	0.0034 (8)	−0.0003 (8)
C3	0.0217 (10)	0.0137 (11)	0.0177 (10)	−0.0015 (9)	0.0038 (8)	−0.0003 (8)
C4	0.0227 (11)	0.0149 (11)	0.0186 (9)	−0.0004 (9)	0.0033 (8)	−0.0014 (8)
C7	0.0184 (10)	0.0161 (10)	0.0169 (9)	0.0033 (9)	0.0015 (8)	0.0004 (8)
C8	0.0184 (10)	0.0184 (11)	0.0224 (10)	0.0040 (9)	0.0046 (8)	0.0024 (8)
C9	0.0203 (11)	0.0260 (12)	0.0229 (11)	0.0006 (10)	0.0044 (9)	−0.0017 (9)
C10	0.0218 (11)	0.0219 (12)	0.0308 (12)	0.0001 (10)	0.0026 (9)	−0.0020 (10)
C11	0.0210 (11)	0.0229 (13)	0.0356 (13)	−0.0017 (10)	0.0073 (10)	0.0055 (10)
C12	0.0270 (12)	0.0271 (12)	0.0311 (12)	0.0001 (11)	0.0133 (10)	0.0032 (10)
C13	0.0259 (12)	0.0217 (12)	0.0226 (11)	0.0002 (10)	0.0063 (9)	−0.0022 (9)
C14	0.0205 (10)	0.0240 (12)	0.0178 (10)	0.0007 (10)	0.0041 (8)	0.0011 (9)
C15	0.0231 (11)	0.0221 (12)	0.0209 (10)	0.0027 (10)	0.0025 (9)	0.0000 (10)
C16	0.0251 (12)	0.0289 (13)	0.0284 (12)	0.0061 (12)	0.0043 (10)	−0.0008 (11)

Geometric parameters (Å, º)

S2—O21	1.4451 (17)	C9—H9	0.96 (2)
S2—O22	1.4413 (15)	C10—C11	1.399 (3)
S2—C1	1.834 (2)	C10—H10	0.98 (2)
S2—C3	1.835 (2)	C11—C12	1.392 (3)
O5—N6	1.411 (2)	C11—H11	0.99 (3)
O5—C4	1.453 (2)	C12—C13	1.395 (3)
N6—C7	1.298 (2)	C12—H12	0.95 (3)
C1—C7	1.502 (3)	C13—H13	0.95 (2)
C1—C4	1.545 (3)	C14—C15	1.538 (3)
C1—H1	0.94 (3)	C14—H14A	0.98 (2)
C3—C14	1.527 (3)	C14—H14B	0.99 (3)
C3—C4	1.557 (3)	C15—C16	1.521 (3)
C3—H3	0.92 (2)	C15—H15A	1.00 (3)
C4—H4	0.96 (3)	C15—H15B	0.99 (2)
C7—C8	1.471 (3)	C16—H16A	0.94 (3)
C8—C9	1.402 (3)	C16—H16B	0.97 (3)
C8—C13	1.404 (3)	C16—H16C	1.01 (3)
C9—C10	1.390 (3)
O22—S2—O21	118.61 (9)	C10—C9—H9	122.4 (16)
O22—S2—C1	113.10 (10)	C8—C9—H9	117.2 (16)
O21—S2—C1	111.41 (10)	C9—C10—C11	120.1 (2)
O22—S2—C3	114.74 (10)	C9—C10—H10	118.9 (14)
O21—S2—C3	112.28 (9)	C11—C10—H10	120.9 (14)
C1—S2—C3	80.68 (10)	C12—C11—C10	120.0 (2)
N6—O5—C4	109.94 (14)	C12—C11—H11	117.9 (15)
C7—N6—O5	110.41 (16)	C10—C11—H11	122.1 (15)
C7—C1—C4	101.85 (16)	C11—C12—C13	120.0 (2)
C7—C1—S2	112.64 (15)	C11—C12—H12	120.4 (17)
C4—C1—S2	89.86 (13)	C13—C12—H12	119.5 (17)
C7—C1—H1	116.6 (16)	C12—C13—C8	120.3 (2)
C4—C1—H1	120.1 (16)	C12—C13—H13	117.8 (14)
S2—C1—H1	112.6 (16)	C8—C13—H13	121.9 (14)
C14—C3—C4	118.08 (17)	C3—C14—C15	114.08 (17)
C14—C3—S2	115.56 (15)	C3—C14—H14A	110.4 (14)
C4—C3—S2	89.46 (13)	C15—C14—H14A	108.7 (14)
C14—C3—H3	112.8 (15)	C3—C14—H14B	105.9 (16)
C4—C3—H3	111.5 (15)	C15—C14—H14B	109.7 (16)
S2—C3—H3	106.8 (14)	H14A—C14—H14B	107.9 (19)
O5—C4—C1	104.82 (17)	C16—C15—C14	112.17 (18)
O5—C4—C3	113.08 (17)	C16—C15—H15A	109.2 (14)
C1—C4—C3	99.92 (16)	C14—C15—H15A	109.1 (14)
O5—C4—H4	108.5 (15)	C16—C15—H15B	111.2 (15)
C1—C4—H4	117.4 (15)	C14—C15—H15B	109.0 (15)
C3—C4—H4	112.8 (16)	H15A—C15—H15B	105.9 (19)
N6—C7—C8	121.25 (19)	C15—C16—H16A	114.3 (18)
N6—C7—C1	112.90 (18)	C15—C16—H16B	107.5 (18)
C8—C7—C1	125.72 (17)	H16A—C16—H16B	104 (3)
C9—C8—C13	119.2 (2)	C15—C16—H16C	109.9 (16)
C9—C8—C7	120.46 (18)	H16A—C16—H16C	111 (2)
C13—C8—C7	120.22 (19)	H16B—C16—H16C	111 (2)
C10—C9—C8	120.3 (2)
C4—O5—N6—C7	−2.9 (2)	S2—C3—C4—C1	−2.29 (15)
O22—S2—C1—C7	142.25 (14)	O5—N6—C7—C8	177.53 (17)
O21—S2—C1—C7	5.65 (18)	O5—N6—C7—C1	1.6 (2)
C3—S2—C1—C7	−104.73 (16)	C4—C1—C7—N6	0.2 (2)
O22—S2—C1—C4	−114.96 (13)	S2—C1—C7—N6	95.10 (19)
O21—S2—C1—C4	108.44 (13)	C4—C1—C7—C8	−175.51 (19)
C3—S2—C1—C4	−1.94 (12)	S2—C1—C7—C8	−80.6 (2)
O22—S2—C3—C14	−125.69 (16)	N6—C7—C8—C9	4.4 (3)
O21—S2—C3—C14	13.66 (19)	C1—C7—C8—C9	179.8 (2)
C1—S2—C3—C14	123.08 (17)	N6—C7—C8—C13	−172.5 (2)
O22—S2—C3—C4	113.16 (14)	C1—C7—C8—C13	3.0 (3)
O21—S2—C3—C4	−107.50 (13)	C13—C8—C9—C10	0.8 (3)
C1—S2—C3—C4	1.93 (12)	C7—C8—C9—C10	−176.0 (2)
N6—O5—C4—C1	2.9 (2)	C8—C9—C10—C11	0.1 (4)
N6—O5—C4—C3	−105.00 (19)	C9—C10—C11—C12	−1.3 (3)
C7—C1—C4—O5	−1.8 (2)	C10—C11—C12—C13	1.5 (4)
S2—C1—C4—O5	−114.97 (14)	C11—C12—C13—C8	−0.6 (4)
C7—C1—C4—C3	115.42 (17)	C9—C8—C13—C12	−0.5 (3)
S2—C1—C4—C3	2.29 (15)	C7—C8—C13—C12	176.3 (2)
C14—C3—C4—O5	−10.3 (3)	C4—C3—C14—C15	176.37 (18)
S2—C3—C4—O5	108.62 (16)	S2—C3—C14—C15	72.3 (2)
C14—C3—C4—C1	−121.24 (19)	C3—C14—C15—C16	−177.7 (2)