1'-(4-Iodo­benz­yl)spiro­[isobenzofuran-1(3H),4'-piperidine]

In the title compound, C₁₉H₂₀INO, the central piperidine ring adopts a chair conformation.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.024
• wR factor = 0.059
• Data-to-parameter ratio = 21.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

1'-(4-Iodobenzyl)spiro[isobenzofuran-1(3H),4'-piperidine]

Crystal data

C19H20INO	F(000) = 808
Mr = 405.26	Dx = 1.633 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 3138 reflections
a = 10.1099 (6) Å	θ = 2.1–28.7°
b = 11.8733 (6) Å	µ = 1.95 mm^−1
c = 14.262 (1) Å	T = 113 K
β = 105.722 (3)°	Prism, colourless
V = 1647.98 (17) Å^3	0.24 × 0.20 × 0.18 mm
Z = 4

Data collection

Rigaku Saturn diffractometer	4225 independent reflections
Radiation source: rotating anode	3599 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.035
Detector resolution: 7.31 pixels mm^-1	θmax = 28.7°, θmin = 2.1°
ω scans	h = −13→13
Absorption correction: multi-scan (Jacobson, 1998)	k = −15→16
Tmin = 0.653, Tmax = 0.721	l = −19→19
15887 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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.059	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0311P)^2 + 0.0811P] where P = (Fo^2 + 2Fc^2)/3
4225 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.81 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
I	0.463290 (14)	0.584069 (11)	0.228124 (9)	0.02029 (5)
O1	1.12953 (14)	1.03075 (12)	0.77960 (10)	0.0192 (3)
N1	0.81044 (18)	0.93273 (13)	0.62877 (13)	0.0174 (4)
C1	1.2262 (2)	1.06980 (16)	0.86721 (15)	0.0187 (4)
H1A	1.1938	1.1404	0.8905	0.022*
H1B	1.3174	1.0833	0.8561	0.022*
C2	1.2331 (2)	0.97590 (16)	0.93930 (14)	0.0152 (4)
C3	1.3267 (2)	0.95761 (17)	1.02961 (14)	0.0185 (4)
H3	1.3981	1.0101	1.0556	0.022*
C4	1.3128 (2)	0.86068 (18)	1.08078 (14)	0.0193 (4)
H4	1.3761	0.8459	1.1421	0.023*
C5	1.2063 (2)	0.78486 (17)	1.04254 (14)	0.0202 (4)
H5	1.1979	0.7190	1.0783	0.024*
C6	1.1122 (2)	0.80452 (17)	0.95278 (14)	0.0187 (4)
H6	1.0390	0.7534	0.9273	0.022*
C7	1.1282 (2)	0.90079 (16)	0.90142 (14)	0.0151 (4)
C8	1.0461 (2)	0.94026 (17)	0.80175 (15)	0.0157 (4)
C9	0.9051 (2)	0.98737 (17)	0.80095 (15)	0.0183 (4)
H9A	0.8509	0.9285	0.8230	0.022*
H9B	0.9165	1.0516	0.8467	0.022*
C10	0.8283 (2)	1.02615 (17)	0.69910 (15)	0.0210 (4)
H10A	0.7371	1.0558	0.6999	0.025*
H10B	0.8801	1.0878	0.6786	0.025*
C11	0.9456 (2)	0.89041 (18)	0.62426 (15)	0.0183 (4)
H11A	0.9964	0.9514	0.6018	0.022*
H11B	0.9326	0.8279	0.5767	0.022*
C12	1.0291 (2)	0.84879 (17)	0.72403 (14)	0.0173 (4)
H12A	1.1209	0.8243	0.7198	0.021*
H12B	0.9826	0.7828	0.7432	0.021*
C13	0.7325 (2)	0.97258 (18)	0.53184 (16)	0.0238 (5)
H13A	0.7934	1.0199	0.5043	0.029*
H13B	0.6557	1.0205	0.5390	0.029*
C14	0.6748 (2)	0.87769 (17)	0.46092 (15)	0.0177 (4)
C15	0.7277 (2)	0.85267 (17)	0.38289 (15)	0.0200 (4)
H15	0.8049	0.8933	0.3750	0.024*
C16	0.6691 (2)	0.76881 (17)	0.31596 (14)	0.0184 (4)
H16	0.7070	0.7513	0.2636	0.022*
C17	0.5549 (2)	0.71153 (16)	0.32695 (14)	0.0157 (4)
C18	0.5003 (2)	0.73494 (16)	0.40414 (14)	0.0180 (4)
H18	0.4216	0.6955	0.4109	0.022*
C19	0.5616 (2)	0.81630 (17)	0.47119 (14)	0.0187 (4)
H19	0.5262	0.8308	0.5253	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I	0.02398 (8)	0.01907 (8)	0.01495 (7)	−0.00094 (5)	0.00036 (5)	−0.00001 (5)
O1	0.0167 (7)	0.0202 (8)	0.0188 (7)	−0.0060 (6)	0.0016 (6)	0.0034 (6)
N1	0.0145 (8)	0.0158 (9)	0.0187 (9)	0.0023 (6)	−0.0011 (7)	−0.0015 (7)
C1	0.0205 (10)	0.0160 (10)	0.0181 (10)	−0.0019 (8)	0.0025 (8)	0.0006 (8)
C2	0.0165 (10)	0.0142 (9)	0.0159 (9)	0.0011 (8)	0.0061 (8)	−0.0016 (8)
C3	0.0210 (11)	0.0174 (10)	0.0163 (10)	−0.0003 (8)	0.0037 (8)	−0.0045 (8)
C4	0.0233 (11)	0.0221 (11)	0.0115 (9)	0.0036 (9)	0.0031 (8)	−0.0012 (8)
C5	0.0289 (12)	0.0170 (10)	0.0171 (10)	0.0023 (8)	0.0103 (9)	0.0022 (8)
C6	0.0201 (10)	0.0188 (10)	0.0179 (10)	−0.0023 (8)	0.0065 (8)	−0.0020 (8)
C7	0.0153 (9)	0.0167 (10)	0.0140 (9)	0.0017 (8)	0.0050 (8)	−0.0022 (7)
C8	0.0156 (10)	0.0154 (10)	0.0162 (9)	−0.0013 (7)	0.0044 (8)	0.0011 (7)
C9	0.0177 (10)	0.0164 (10)	0.0206 (10)	0.0000 (8)	0.0049 (8)	−0.0043 (8)
C10	0.0177 (10)	0.0172 (10)	0.0254 (11)	0.0023 (8)	0.0012 (9)	−0.0037 (9)
C11	0.0165 (10)	0.0206 (10)	0.0162 (10)	0.0015 (8)	0.0014 (8)	−0.0010 (8)
C12	0.0158 (10)	0.0202 (10)	0.0149 (10)	0.0038 (8)	0.0026 (8)	−0.0011 (8)
C13	0.0245 (12)	0.0171 (11)	0.0232 (11)	0.0017 (9)	−0.0047 (9)	0.0009 (9)
C14	0.0167 (10)	0.0131 (9)	0.0183 (10)	0.0024 (8)	−0.0037 (8)	0.0038 (8)
C15	0.0146 (10)	0.0189 (10)	0.0243 (11)	−0.0019 (8)	0.0019 (8)	0.0060 (8)
C16	0.0192 (10)	0.0193 (10)	0.0174 (10)	0.0022 (8)	0.0063 (8)	0.0054 (8)
C17	0.0177 (10)	0.0131 (9)	0.0139 (9)	0.0001 (7)	0.0003 (8)	0.0017 (7)
C18	0.0166 (10)	0.0179 (10)	0.0197 (10)	−0.0004 (8)	0.0051 (8)	0.0028 (8)
C19	0.0193 (10)	0.0191 (10)	0.0171 (10)	0.0020 (8)	0.0038 (8)	0.0005 (8)

Geometric parameters (Å, º)

I—C17	2.104 (2)	C9—H9A	0.9900
O1—C1	1.439 (2)	C9—H9B	0.9900
O1—C8	1.453 (2)	C10—H10A	0.9900
N1—C13	1.471 (3)	C10—H10B	0.9900
N1—C10	1.473 (3)	C11—C12	1.527 (3)
N1—C11	1.473 (3)	C11—H11A	0.9900
C1—C2	1.505 (3)	C11—H11B	0.9900
C1—H1A	0.9900	C12—H12A	0.9900
C1—H1B	0.9900	C12—H12B	0.9900
C2—C7	1.379 (3)	C13—C14	1.521 (3)
C2—C3	1.393 (3)	C13—H13A	0.9900
C3—C4	1.390 (3)	C13—H13B	0.9900
C3—H3	0.9500	C14—C15	1.391 (3)
C4—C5	1.396 (3)	C14—C19	1.398 (3)
C4—H4	0.9500	C15—C16	1.395 (3)
C5—C6	1.392 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—C17	1.385 (3)
C6—C7	1.390 (3)	C16—H16	0.9500
C6—H6	0.9500	C17—C18	1.387 (3)
C7—C8	1.513 (3)	C18—C19	1.382 (3)
C8—C12	1.528 (3)	C18—H18	0.9500
C8—C9	1.528 (3)	C19—H19	0.9500
C9—C10	1.521 (3)
C1—O1—C8	110.32 (15)	N1—C10—H10A	109.4
C13—N1—C10	109.46 (16)	C9—C10—H10A	109.4
C13—N1—C11	109.59 (17)	N1—C10—H10B	109.4
C10—N1—C11	110.02 (16)	C9—C10—H10B	109.4
O1—C1—C2	104.46 (15)	H10A—C10—H10B	108.0
O1—C1—H1A	110.9	N1—C11—C12	110.80 (17)
C2—C1—H1A	110.9	N1—C11—H11A	109.5
O1—C1—H1B	110.9	C12—C11—H11A	109.5
C2—C1—H1B	110.9	N1—C11—H11B	109.5
H1A—C1—H1B	108.9	C12—C11—H11B	109.5
C7—C2—C3	121.25 (18)	H11A—C11—H11B	108.1
C7—C2—C1	108.82 (17)	C11—C12—C8	111.78 (17)
C3—C2—C1	129.91 (19)	C11—C12—H12A	109.3
C4—C3—C2	118.3 (2)	C8—C12—H12A	109.3
C4—C3—H3	120.8	C11—C12—H12B	109.3
C2—C3—H3	120.8	C8—C12—H12B	109.3
C3—C4—C5	120.38 (19)	H12A—C12—H12B	107.9
C3—C4—H4	119.8	N1—C13—C14	113.44 (17)
C5—C4—H4	119.8	N1—C13—H13A	108.9
C6—C5—C4	120.89 (19)	C14—C13—H13A	108.9
C6—C5—H5	119.6	N1—C13—H13B	108.9
C4—C5—H5	119.6	C14—C13—H13B	108.9
C7—C6—C5	118.3 (2)	H13A—C13—H13B	107.7
C7—C6—H6	120.8	C15—C14—C19	118.39 (19)
C5—C6—H6	120.8	C15—C14—C13	121.96 (19)
C2—C7—C6	120.79 (19)	C19—C14—C13	119.6 (2)
C2—C7—C8	109.62 (17)	C14—C15—C16	121.06 (19)
C6—C7—C8	129.57 (19)	C14—C15—H15	119.5
O1—C8—C7	103.30 (16)	C16—C15—H15	119.5
O1—C8—C12	108.98 (17)	C17—C16—C15	119.04 (18)
C7—C8—C12	112.73 (17)	C17—C16—H16	120.5
O1—C8—C9	108.86 (16)	C15—C16—H16	120.5
C7—C8—C9	113.18 (17)	C16—C17—C18	120.98 (18)
C12—C8—C9	109.50 (17)	C16—C17—I	120.43 (15)
C10—C9—C8	110.56 (17)	C18—C17—I	118.58 (15)
C10—C9—H9A	109.5	C19—C18—C17	119.27 (19)
C8—C9—H9A	109.5	C19—C18—H18	120.4
C10—C9—H9B	109.5	C17—C18—H18	120.4
C8—C9—H9B	109.5	C18—C19—C14	121.23 (19)
H9A—C9—H9B	108.1	C18—C19—H19	119.4
N1—C10—C9	111.04 (17)	C14—C19—H19	119.4
C8—O1—C1—C2	18.6 (2)	C12—C8—C9—C10	−53.7 (2)
O1—C1—C2—C7	−11.4 (2)	C13—N1—C10—C9	178.40 (18)
O1—C1—C2—C3	167.0 (2)	C11—N1—C10—C9	−61.1 (2)
C7—C2—C3—C4	0.6 (3)	C8—C9—C10—N1	58.7 (2)
C1—C2—C3—C4	−177.6 (2)	C13—N1—C11—C12	179.80 (16)
C2—C3—C4—C5	−0.8 (3)	C10—N1—C11—C12	59.4 (2)
C3—C4—C5—C6	0.1 (3)	N1—C11—C12—C8	−56.2 (2)
C4—C5—C6—C7	0.9 (3)	O1—C8—C12—C11	−66.1 (2)
C3—C2—C7—C6	0.4 (3)	C7—C8—C12—C11	179.81 (16)
C1—C2—C7—C6	178.92 (18)	C9—C8—C12—C11	52.9 (2)
C3—C2—C7—C8	−178.26 (18)	C10—N1—C13—C14	−164.14 (18)
C1—C2—C7—C8	0.3 (2)	C11—N1—C13—C14	75.1 (2)
C5—C6—C7—C2	−1.1 (3)	N1—C13—C14—C15	−108.6 (2)
C5—C6—C7—C8	177.17 (19)	N1—C13—C14—C19	74.2 (2)
C1—O1—C8—C7	−18.3 (2)	C19—C14—C15—C16	0.3 (3)
C1—O1—C8—C12	−138.34 (17)	C13—C14—C15—C16	−176.90 (18)
C1—O1—C8—C9	102.29 (18)	C14—C15—C16—C17	1.2 (3)
C2—C7—C8—O1	10.7 (2)	C15—C16—C17—C18	−1.2 (3)
C6—C7—C8—O1	−167.75 (19)	C15—C16—C17—I	−179.81 (14)
C2—C7—C8—C12	128.19 (18)	C16—C17—C18—C19	−0.4 (3)
C6—C7—C8—C12	−50.3 (3)	I—C17—C18—C19	178.24 (14)
C2—C7—C8—C9	−106.85 (19)	C17—C18—C19—C14	2.0 (3)
C6—C7—C8—C9	74.7 (3)	C15—C14—C19—C18	−2.0 (3)
O1—C8—C9—C10	65.4 (2)	C13—C14—C19—C18	175.32 (18)
C7—C8—C9—C10	179.63 (16)