N,N-Dicyclo­hexyl-2-iodo­acetamide

In the crystal structure of the title compound, C₁₄H₂₄INO, the sum of the angles around the N atom is 359.9°, implying a planar configuration.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.023
• wR factor = 0.049
• Data-to-parameter ratio = 23.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT410_ALERT_2_C Short Intra H...H Contact  H7A    ..  H14B    ..       1.94 Ang.

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           28.32
           From the CIF: _reflns_number_total               3702
           Count of symmetry unique reflns         2149
           Completeness (_total/calc)            172.27%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1553
           Fraction of Friedel pairs measured     0.723
           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
   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

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: XCIF (Bruker, 2001).

N,N-Dicyclohexyl-2-iodoacetamide

Crystal data

C14H24INO	F(000) = 704
Mr = 349.24	Dx = 1.538 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 939 reflections
a = 10.576 (2) Å	θ = 3.1–27.7°
b = 11.049 (2) Å	µ = 2.11 mm^−1
c = 12.907 (3) Å	T = 193 K
V = 1508.2 (5) Å^3	Prism, colorless
Z = 4	0.25 × 0.22 × 0.15 mm

Data collection

Siemens Platform/CCD diffractometer	3702 independent reflections
Radiation source: normal-focus sealed tube	3273 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Profile data from ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: integration (SHELXTL/XPREP; Bruker, 2001)	h = −13→13
Tmin = 0.536, Tmax = 0.776	k = −14→14
14614 measured reflections	l = −17→17

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.023	w = 1/[σ^2(Fo^2) + (0.0231P)^2 + 0.2165P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.049	(Δ/σ)max = 0.002
S = 1.02	Δρmax = 0.40 e Å^−3
3702 reflections	Δρmin = −0.51 e Å^−3
155 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0010 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1569 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.015 (16)

Special details

Experimental. One distinct cell was identified using SMART (Bruker, 2001). Five frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2001) then corrected for absorption by integration using SHELXTL/XPREP (Bruker, 2001) before using SAINT/SADABS (Bruker, 2001) to sort, merge, and scale the combined data. A series of identical frames was collected twice during the experiment to monitor decay. No decay correction was applied.

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. Systematic conditions suggested the unambiguous space group. Structure was phased by direct methods. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F². The highest peaks in the final difference Fourier map were in the vicinity of atom I1; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed little dependence on amplitude or resolution.

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

	x	y	z	Uiso*/Ueq
C1	0.53675 (19)	0.45334 (18)	0.32821 (16)	0.0273 (4)
H1A	0.4897	0.5285	0.3088	0.033*
C2	0.6683 (2)	0.4948 (2)	0.36199 (18)	0.0312 (5)
H2A	0.7210	0.4234	0.3789	0.037*
H2B	0.6615	0.5456	0.4249	0.037*
C3	0.7307 (2)	0.5674 (2)	0.27502 (19)	0.0363 (5)
H3A	0.6828	0.6433	0.2639	0.044*
H3B	0.8178	0.5893	0.2959	0.044*
C4	0.7354 (2)	0.4960 (2)	0.17362 (19)	0.0358 (5)
H4A	0.7695	0.5483	0.1180	0.043*
H4B	0.7929	0.4260	0.1817	0.043*
C5	0.6043 (2)	0.4511 (2)	0.14288 (18)	0.0362 (5)
H5A	0.6112	0.4008	0.0797	0.043*
H5B	0.5497	0.5214	0.1266	0.043*
C6	0.5432 (2)	0.3764 (2)	0.22981 (16)	0.0324 (4)
H6A	0.4570	0.3513	0.2090	0.039*
H6B	0.5939	0.3026	0.2429	0.039*
C7	0.3556 (2)	0.4662 (2)	0.45489 (18)	0.0294 (5)
H7A	0.3206	0.4185	0.5142	0.035*
C8	0.2483 (2)	0.4820 (2)	0.3771 (2)	0.0369 (6)
H8A	0.2201	0.4018	0.3517	0.044*
H8B	0.2781	0.5297	0.3169	0.044*
C9	0.1377 (2)	0.5476 (2)	0.4299 (2)	0.0429 (6)
H9A	0.0690	0.5606	0.3790	0.051*
H9B	0.1040	0.4963	0.4865	0.051*
C10	0.1789 (3)	0.6692 (2)	0.4742 (2)	0.0510 (7)
H10A	0.2051	0.7232	0.4169	0.061*
H10B	0.1066	0.7075	0.5102	0.061*
C11	0.2877 (3)	0.6542 (2)	0.5495 (2)	0.0489 (6)
H11A	0.2586	0.6079	0.6107	0.059*
H11B	0.3158	0.7349	0.5736	0.059*
C12	0.3995 (2)	0.5880 (2)	0.4991 (2)	0.0374 (5)
H12A	0.4352	0.6384	0.4429	0.045*
H12B	0.4665	0.5743	0.5513	0.045*
C13	0.49794 (19)	0.2867 (2)	0.44988 (16)	0.0287 (4)
C14	0.4115 (2)	0.2236 (2)	0.52726 (16)	0.0311 (4)
H14A	0.4221	0.1348	0.5214	0.037*
H14B	0.3223	0.2433	0.5113	0.037*
I1	0.454920 (17)	0.279969 (18)	0.681798 (13)	0.05020 (7)
N1	0.46241 (18)	0.39580 (15)	0.41234 (13)	0.0276 (3)
O1	0.59509 (15)	0.23407 (15)	0.42309 (13)	0.0387 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0258 (9)	0.0263 (9)	0.0299 (10)	0.0003 (8)	0.0019 (10)	0.0035 (8)
C2	0.0303 (12)	0.0360 (13)	0.0274 (11)	−0.0026 (9)	0.0014 (9)	−0.0008 (10)
C3	0.0332 (12)	0.0374 (13)	0.0382 (12)	−0.0101 (10)	0.0062 (10)	−0.0017 (11)
C4	0.0349 (11)	0.0415 (13)	0.0310 (12)	−0.0024 (9)	0.0084 (11)	0.0016 (12)
C5	0.0422 (13)	0.0401 (13)	0.0263 (10)	0.0023 (11)	−0.0003 (10)	0.0021 (10)
C6	0.0318 (11)	0.0349 (12)	0.0306 (10)	−0.0050 (11)	0.0024 (10)	−0.0011 (9)
C7	0.0269 (11)	0.0276 (11)	0.0337 (11)	0.0030 (9)	0.0068 (9)	0.0031 (10)
C8	0.0266 (12)	0.0373 (14)	0.0466 (14)	0.0027 (9)	0.0039 (10)	0.0040 (11)
C9	0.0283 (12)	0.0426 (14)	0.0577 (17)	0.0057 (11)	0.0079 (11)	0.0150 (13)
C10	0.0459 (14)	0.0399 (14)	0.0673 (18)	0.0161 (12)	0.0236 (13)	0.0103 (14)
C11	0.0580 (16)	0.0380 (14)	0.0508 (15)	0.0091 (13)	0.0165 (13)	−0.0079 (13)
C12	0.0386 (12)	0.0338 (13)	0.0397 (13)	0.0015 (10)	0.0047 (10)	−0.0062 (10)
C13	0.0287 (9)	0.0261 (10)	0.0314 (10)	−0.0016 (9)	0.0016 (8)	0.0001 (10)
C14	0.0325 (10)	0.0265 (10)	0.0343 (11)	−0.0033 (10)	0.0040 (8)	0.0017 (10)
I1	0.05316 (10)	0.06507 (12)	0.03237 (8)	−0.01787 (9)	−0.00254 (8)	0.00048 (8)
N1	0.0253 (8)	0.0259 (8)	0.0317 (9)	0.0009 (8)	0.0059 (8)	0.0042 (7)
O1	0.0345 (8)	0.0339 (9)	0.0478 (9)	0.0099 (7)	0.0122 (7)	0.0116 (8)

Geometric parameters (Å, º)

C1—N1	1.484 (3)	C7—H7A	1.0000
C1—C2	1.529 (3)	C8—C9	1.536 (3)
C1—C6	1.530 (3)	C8—H8A	0.9900
C1—H1A	1.0000	C8—H8B	0.9900
C2—C3	1.529 (3)	C9—C10	1.523 (4)
C2—H2A	0.9900	C9—H9A	0.9900
C2—H2B	0.9900	C9—H9B	0.9900
C3—C4	1.529 (3)	C10—C11	1.516 (4)
C3—H3A	0.9900	C10—H10A	0.9900
C3—H3B	0.9900	C10—H10B	0.9900
C4—C5	1.524 (3)	C11—C12	1.535 (3)
C4—H4A	0.9900	C11—H11A	0.9900
C4—H4B	0.9900	C11—H11B	0.9900
C5—C6	1.536 (3)	C12—H12A	0.9900
C5—H5A	0.9900	C12—H12B	0.9900
C5—H5B	0.9900	C13—O1	1.230 (3)
C6—H6A	0.9900	C13—N1	1.353 (3)
C6—H6B	0.9900	C13—C14	1.523 (3)
C7—N1	1.478 (3)	C14—I1	2.140 (2)
C7—C8	1.526 (3)	C14—H14A	0.9900
C7—C12	1.533 (3)	C14—H14B	0.9900
N1—C1—C2	113.71 (17)	C7—C8—C9	109.1 (2)
N1—C1—C6	113.14 (17)	C7—C8—H8A	109.9
C2—C1—C6	111.25 (18)	C9—C8—H8A	109.9
N1—C1—H1A	106.0	C7—C8—H8B	109.9
C2—C1—H1A	106.0	C9—C8—H8B	109.9
C6—C1—H1A	106.0	H8A—C8—H8B	108.3
C1—C2—C3	109.90 (19)	C10—C9—C8	111.4 (2)
C1—C2—H2A	109.7	C10—C9—H9A	109.3
C3—C2—H2A	109.7	C8—C9—H9A	109.3
C1—C2—H2B	109.7	C10—C9—H9B	109.3
C3—C2—H2B	109.7	C8—C9—H9B	109.3
H2A—C2—H2B	108.2	H9A—C9—H9B	108.0
C4—C3—C2	111.8 (2)	C11—C10—C9	111.2 (2)
C4—C3—H3A	109.2	C11—C10—H10A	109.4
C2—C3—H3A	109.2	C9—C10—H10A	109.4
C4—C3—H3B	109.2	C11—C10—H10B	109.4
C2—C3—H3B	109.2	C9—C10—H10B	109.4
H3A—C3—H3B	107.9	H10A—C10—H10B	108.0
C5—C4—C3	111.18 (19)	C10—C11—C12	111.4 (2)
C5—C4—H4A	109.4	C10—C11—H11A	109.3
C3—C4—H4A	109.4	C12—C11—H11A	109.3
C5—C4—H4B	109.4	C10—C11—H11B	109.3
C3—C4—H4B	109.4	C12—C11—H11B	109.3
H4A—C4—H4B	108.0	H11A—C11—H11B	108.0
C4—C5—C6	111.6 (2)	C7—C12—C11	110.0 (2)
C4—C5—H5A	109.3	C7—C12—H12A	109.7
C6—C5—H5A	109.3	C11—C12—H12A	109.7
C4—C5—H5B	109.3	C7—C12—H12B	109.7
C6—C5—H5B	109.3	C11—C12—H12B	109.7
H5A—C5—H5B	108.0	H12A—C12—H12B	108.2
C1—C6—C5	109.05 (18)	O1—C13—N1	123.5 (2)
C1—C6—H6A	109.9	O1—C13—C14	118.0 (2)
C5—C6—H6A	109.9	N1—C13—C14	118.43 (18)
C1—C6—H6B	109.9	C13—C14—I1	110.44 (14)
C5—C6—H6B	109.9	C13—C14—H14A	109.6
H6A—C6—H6B	108.3	I1—C14—H14A	109.6
N1—C7—C8	112.6 (2)	C13—C14—H14B	109.6
N1—C7—C12	111.64 (18)	I1—C14—H14B	109.6
C8—C7—C12	111.8 (2)	H14A—C14—H14B	108.1
N1—C7—H7A	106.8	C13—N1—C7	123.27 (17)
C8—C7—H7A	106.8	C13—N1—C1	119.80 (17)
C12—C7—H7A	106.8	C7—N1—C1	116.84 (16)
N1—C1—C2—C3	−172.56 (18)	C10—C11—C12—C7	−55.3 (3)
C6—C1—C2—C3	58.3 (2)	O1—C13—C14—I1	93.9 (2)
C1—C2—C3—C4	−55.4 (3)	N1—C13—C14—I1	−87.8 (2)
C2—C3—C4—C5	54.2 (3)	O1—C13—N1—C7	−171.3 (2)
C3—C4—C5—C6	−55.2 (3)	C14—C13—N1—C7	10.5 (3)
N1—C1—C6—C5	171.58 (17)	O1—C13—N1—C1	5.1 (3)
C2—C1—C6—C5	−59.0 (2)	C14—C13—N1—C1	−173.11 (18)
C4—C5—C6—C1	57.2 (3)	C8—C7—N1—C13	−115.6 (2)
N1—C7—C8—C9	175.84 (18)	C12—C7—N1—C13	117.8 (2)
C12—C7—C8—C9	−57.6 (3)	C8—C7—N1—C1	67.9 (2)
C7—C8—C9—C10	57.0 (3)	C12—C7—N1—C1	−58.7 (3)
C8—C9—C10—C11	−56.7 (3)	C2—C1—N1—C13	−68.7 (2)
C9—C10—C11—C12	55.6 (3)	C6—C1—N1—C13	59.4 (3)
N1—C7—C12—C11	−175.9 (2)	C2—C1—N1—C7	107.9 (2)
C8—C7—C12—C11	57.0 (3)	C6—C1—N1—C7	−123.9 (2)