Synthesis and crystal structure of tert-butyl 1-(2-iodo­benzo­yl)cyclo­pent-3-ene-1-carboxyl­ate

The cyclo­pent-3-ene ring has an envelope conformation with the tertiary C atom as the flap atom.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.051
• wR factor = 0.131
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C14 Check

Alert level G
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   1 ALERT level G = General information/check it is not something unexpected

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

tert-Butyl 1-(2-iodobenzoyl)-cyclopent-3-ene-1-carboxylate

Crystal data

C17H19IO3	F(000) = 792
Mr = 398.22	Dx = 1.533 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 9.4977 (2) Å	Cell parameters from 5961 reflections
b = 9.3635 (2) Å	θ = 4.6–69.9°
c = 19.8978 (4) Å	µ = 14.64 mm^−1
β = 102.752 (1)°	T = 299 K
V = 1725.90 (6) Å^3	Block, colourless
Z = 4	0.3 × 0.2 × 0.1 mm

Data collection

Bruker APEXII CCD diffractometer	2612 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.066
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θmax = 70.1°, θmin = 4.6°
Tmin = 0.262, Tmax = 0.753	h = −10→11
16056 measured reflections	k = −11→11
3278 independent reflections	l = −24→22

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0548P)^2 + 2.0895P] where P = (Fo^2 + 2Fc^2)/3
3278 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.61 e Å^−3
0 restraints	Δρmin = −1.22 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.22879 (4)	0.41049 (5)	0.17053 (2)	0.0858 (2)
O1	0.1852 (4)	0.6510 (4)	0.28314 (19)	0.0681 (9)
C1	0.3928 (4)	0.5060 (4)	0.3155 (2)	0.0425 (8)
O2	0.2177 (3)	0.3021 (3)	0.37481 (14)	0.0444 (6)
C2	0.5151 (4)	0.5150 (5)	0.3679 (2)	0.0489 (9)
H2	0.509986	0.562449	0.408373	0.059*
O3	0.3190 (4)	0.3762 (3)	0.48200 (17)	0.0596 (8)
C3	0.6447 (5)	0.4554 (6)	0.3617 (3)	0.0581 (12)
H3	0.726078	0.463818	0.397392	0.07*
C4	0.6522 (5)	0.3836 (6)	0.3024 (3)	0.0647 (13)
H4	0.738876	0.34243	0.298079	0.078*
C7	0.2544 (4)	0.5741 (4)	0.3257 (2)	0.0442 (9)
C6	0.4034 (5)	0.4366 (5)	0.2548 (2)	0.0496 (10)
C5	0.5325 (5)	0.3725 (6)	0.2497 (3)	0.0613 (12)
H5	0.537768	0.321576	0.21015	0.074*
C8	0.2122 (4)	0.5470 (4)	0.3950 (2)	0.0407 (8)
C9	0.0444 (4)	0.5578 (5)	0.3866 (3)	0.0528 (11)
H9A	−0.000447	0.601873	0.342983	0.063*
H9B	0.002167	0.464174	0.389089	0.063*
C10	0.0274 (5)	0.6489 (5)	0.4456 (3)	0.0600 (12)
H10	−0.060286	0.663186	0.458092	0.072*
C11	0.1492 (6)	0.7068 (5)	0.4781 (3)	0.0612 (12)
H11	0.156817	0.766726	0.515951	0.073*
C12	0.2749 (5)	0.6666 (5)	0.4479 (2)	0.0506 (10)
H12A	0.354422	0.630768	0.483133	0.061*
H12B	0.307966	0.747473	0.425131	0.061*
C13	0.2590 (4)	0.4002 (4)	0.4236 (2)	0.0397 (8)
C14	0.2441 (5)	0.1481 (5)	0.3876 (3)	0.0530 (10)
C15	0.1631 (9)	0.0987 (6)	0.4407 (4)	0.091 (2)
H15A	0.070819	0.145176	0.432802	0.137*
H15B	0.217624	0.122419	0.485973	0.137*
H15C	0.149492	−0.002829	0.437233	0.137*
C16	0.1791 (7)	0.0833 (6)	0.3183 (3)	0.0763 (16)
H16A	0.079978	0.112254	0.304044	0.114*
H16B	0.184221	−0.018889	0.321627	0.114*
H16C	0.231621	0.115416	0.285077	0.114*
C17	0.4050 (6)	0.1218 (6)	0.4074 (4)	0.0851 (19)
H17A	0.450457	0.165224	0.373923	0.128*
H17B	0.423246	0.020849	0.408884	0.128*
H17C	0.443561	0.16255	0.451908	0.128*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0721 (3)	0.1182 (4)	0.0569 (2)	−0.0009 (2)	−0.00751 (17)	−0.0218 (2)
O1	0.0613 (19)	0.078 (2)	0.065 (2)	0.0208 (17)	0.0140 (17)	0.0253 (18)
C1	0.0403 (19)	0.045 (2)	0.042 (2)	−0.0023 (16)	0.0093 (16)	0.0044 (17)
O2	0.0465 (14)	0.0380 (14)	0.0462 (15)	−0.0051 (11)	0.0046 (12)	−0.0032 (12)
C2	0.041 (2)	0.059 (3)	0.046 (2)	−0.0017 (18)	0.0091 (17)	−0.002 (2)
O3	0.074 (2)	0.0489 (17)	0.0468 (18)	0.0025 (14)	−0.0058 (15)	0.0017 (14)
C3	0.036 (2)	0.079 (3)	0.058 (3)	−0.002 (2)	0.0082 (19)	0.004 (2)
C4	0.046 (2)	0.083 (4)	0.068 (3)	0.010 (2)	0.019 (2)	0.002 (3)
C7	0.040 (2)	0.046 (2)	0.045 (2)	−0.0018 (17)	0.0072 (17)	0.0028 (18)
C6	0.045 (2)	0.058 (3)	0.043 (2)	−0.0054 (18)	0.0062 (17)	−0.0026 (19)
C5	0.067 (3)	0.069 (3)	0.053 (3)	0.003 (2)	0.024 (2)	−0.010 (2)
C8	0.0350 (18)	0.043 (2)	0.045 (2)	−0.0019 (15)	0.0090 (15)	−0.0025 (17)
C9	0.0351 (19)	0.063 (3)	0.062 (3)	0.0045 (18)	0.0126 (18)	0.005 (2)
C10	0.059 (3)	0.061 (3)	0.066 (3)	0.020 (2)	0.028 (2)	0.014 (2)
C11	0.084 (3)	0.044 (2)	0.062 (3)	0.012 (2)	0.029 (3)	0.001 (2)
C12	0.057 (2)	0.043 (2)	0.053 (2)	−0.0029 (18)	0.015 (2)	−0.0033 (19)
C13	0.0361 (18)	0.042 (2)	0.041 (2)	−0.0002 (15)	0.0096 (16)	0.0013 (16)
C14	0.057 (2)	0.035 (2)	0.068 (3)	−0.0008 (18)	0.016 (2)	−0.004 (2)
C15	0.143 (6)	0.051 (3)	0.096 (5)	−0.019 (3)	0.061 (5)	0.000 (3)
C16	0.087 (4)	0.057 (3)	0.082 (4)	−0.007 (3)	0.013 (3)	−0.024 (3)
C17	0.067 (3)	0.063 (3)	0.117 (5)	0.021 (3)	0.002 (3)	−0.008 (3)

Geometric parameters (Å, º)

I1—C6	2.096 (4)	C9—H9A	0.97
O1—C7	1.193 (5)	C9—H9B	0.97
C1—C2	1.382 (6)	C10—C11	1.312 (8)
C1—C6	1.395 (6)	C10—H10	0.93
C1—C7	1.514 (5)	C11—C12	1.497 (6)
O2—C13	1.331 (5)	C11—H11	0.93
O2—C14	1.476 (5)	C12—H12A	0.97
C2—C3	1.382 (6)	C12—H12B	0.97
C2—H2	0.93	C14—C16	1.508 (8)
O3—C13	1.197 (5)	C14—C15	1.511 (8)
C3—C4	1.373 (7)	C14—C17	1.512 (7)
C3—H3	0.93	C15—H15A	0.96
C4—C5	1.371 (7)	C15—H15B	0.96
C4—H4	0.93	C15—H15C	0.96
C7—C8	1.540 (6)	C16—H16A	0.96
C6—C5	1.389 (7)	C16—H16B	0.96
C5—H5	0.93	C16—H16C	0.96
C8—C13	1.516 (5)	C17—H17A	0.96
C8—C12	1.561 (6)	C17—H17B	0.96
C8—C9	1.568 (5)	C17—H17C	0.96
C9—C10	1.489 (7)
C2—C1—C6	118.2 (4)	C10—C11—C12	113.1 (4)
C2—C1—C7	118.9 (4)	C10—C11—H11	123.4
C6—C1—C7	122.9 (4)	C12—C11—H11	123.4
C13—O2—C14	122.5 (3)	C11—C12—C8	103.4 (4)
C1—C2—C3	121.7 (4)	C11—C12—H12A	111.1
C1—C2—H2	119.2	C8—C12—H12A	111.1
C3—C2—H2	119.2	C11—C12—H12B	111.1
C4—C3—C2	119.4 (4)	C8—C12—H12B	111.1
C4—C3—H3	120.3	H12A—C12—H12B	109.1
C2—C3—H3	120.3	O3—C13—O2	125.3 (4)
C5—C4—C3	120.2 (4)	O3—C13—C8	124.9 (4)
C5—C4—H4	119.9	O2—C13—C8	109.7 (3)
C3—C4—H4	119.9	O2—C14—C16	102.5 (4)
O1—C7—C1	121.2 (4)	O2—C14—C15	109.0 (4)
O1—C7—C8	121.5 (4)	C16—C14—C15	110.4 (5)
C1—C7—C8	117.1 (3)	O2—C14—C17	109.1 (4)
C5—C6—C1	119.9 (4)	C16—C14—C17	111.1 (5)
C5—C6—I1	116.5 (3)	C15—C14—C17	114.1 (6)
C1—C6—I1	123.4 (3)	C14—C15—H15A	109.5
C4—C5—C6	120.5 (4)	C14—C15—H15B	109.5
C4—C5—H5	119.8	H15A—C15—H15B	109.5
C6—C5—H5	119.8	C14—C15—H15C	109.5
C13—C8—C7	111.9 (3)	H15A—C15—H15C	109.5
C13—C8—C12	111.1 (3)	H15B—C15—H15C	109.5
C7—C8—C12	110.5 (3)	C14—C16—H16A	109.5
C13—C8—C9	107.8 (3)	C14—C16—H16B	109.5
C7—C8—C9	110.7 (3)	H16A—C16—H16B	109.5
C12—C8—C9	104.7 (3)	C14—C16—H16C	109.5
C10—C9—C8	103.7 (4)	H16A—C16—H16C	109.5
C10—C9—H9A	111.0	H16B—C16—H16C	109.5
C8—C9—H9A	111.0	C14—C17—H17A	109.5
C10—C9—H9B	111.0	C14—C17—H17B	109.5
C8—C9—H9B	111.0	H17A—C17—H17B	109.5
H9A—C9—H9B	109.0	C14—C17—H17C	109.5
C11—C10—C9	112.8 (4)	H17A—C17—H17C	109.5
C11—C10—H10	123.6	H17B—C17—H17C	109.5
C9—C10—H10	123.6
C6—C1—C2—C3	−1.1 (7)	C13—C8—C9—C10	104.1 (4)
C7—C1—C2—C3	−179.9 (4)	C7—C8—C9—C10	−133.3 (4)
C1—C2—C3—C4	−0.9 (7)	C12—C8—C9—C10	−14.3 (5)
C2—C3—C4—C5	0.6 (8)	C8—C9—C10—C11	9.5 (5)
C2—C1—C7—O1	130.7 (5)	C9—C10—C11—C12	−0.2 (6)
C6—C1—C7—O1	−48.0 (6)	C10—C11—C12—C8	−9.2 (5)
C2—C1—C7—C8	−45.7 (5)	C13—C8—C12—C11	−101.9 (4)
C6—C1—C7—C8	135.7 (4)	C7—C8—C12—C11	133.3 (4)
C2—C1—C6—C5	3.4 (6)	C9—C8—C12—C11	14.1 (4)
C7—C1—C6—C5	−177.9 (4)	C14—O2—C13—O3	−0.9 (6)
C2—C1—C6—I1	179.2 (3)	C14—O2—C13—C8	−178.2 (3)
C7—C1—C6—I1	−2.2 (6)	C7—C8—C13—O3	133.6 (4)
C3—C4—C5—C6	1.7 (8)	C12—C8—C13—O3	9.6 (5)
C1—C6—C5—C4	−3.7 (7)	C9—C8—C13—O3	−104.5 (5)
I1—C6—C5—C4	−179.8 (4)	C7—C8—C13—O2	−49.1 (4)
O1—C7—C8—C13	150.6 (4)	C12—C8—C13—O2	−173.1 (3)
C1—C7—C8—C13	−33.0 (5)	C9—C8—C13—O2	72.8 (4)
O1—C7—C8—C12	−85.0 (5)	C13—O2—C14—C16	−180.0 (4)
C1—C7—C8—C12	91.3 (4)	C13—O2—C14—C15	63.0 (6)
O1—C7—C8—C9	30.4 (6)	C13—O2—C14—C17	−62.2 (6)
C1—C7—C8—C9	−153.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3^i	0.93	2.48	3.219 (5)	136

Symmetry code: (i) −x+1, −y+1, −z+1.