1-Phenyl­decane

In the crystal structure of the title compound, C₁₆H₂₆, the crystal packing is formed by a herring-bone arrangement of the phenyl rings.

Key indicators

• Single-crystal X-ray study
• T = 213 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.124
• Data-to-parameter ratio = 13.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



CRYSR_01  Alert C _exptl_crystal_size_rad not in the CIF when expected.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.00
         From the CIF: _reflns_number_total               1941
         Count of symmetry unique reflns         1533
         Completeness (_total/calc)            126.61%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       408
         Fraction of Friedel pairs measured     0.266
         Are heavy atom types Z>Si present           no
          ALERT: MoKa measured Friedel data cannot be used to
                 determine absolute structure in a light-atom
                 study EXCEPT under VERY special conditions.
                 It is preferred that Friedel data is merged in such cases.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Siemens, 1996); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C16H26	Dx = 0.999 Mg m^−3
Mr = 218.37	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 95 reflections
a = 5.1428 (16) Å	θ = 2.8–18.7°
b = 8.908 (3) Å	µ = 0.06 mm^−1
c = 31.687 (11) Å	T = 213 K
V = 1451.7 (8) Å^3	Cylinder, colourless
Z = 4	0.4 × 0.2 × 0.2 mm
F(000) = 488

Data collection

Bruker AXS CCD 1000 diffractometer	1941 independent reflections
Radiation source: fine-focus sealed tube	1287 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: empirical (using intensity measurements) (Blessing, 1995)	h = −2→7
Tmin = 0.970, Tmax = 0.991	k = −10→11
6337 measured reflections	l = −33→37

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0515P)^2 + 0.1408P] where P = (Fo^2 + 2Fc^2)/3
1941 reflections	(Δ/σ)max = 0.002
145 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.15 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
C12	0.8879 (5)	0.4795 (2)	0.97682 (6)	0.0456 (5)
H12A	0.9132	0.5678	0.9588	0.055*
H12B	0.7002	0.4645	0.9801	0.055*
C10	0.8846 (5)	0.3120 (2)	0.91177 (6)	0.0460 (5)
H10A	0.9124	0.3997	0.8936	0.055*
H10B	0.6966	0.2984	0.9150	0.055*
C14	0.8918 (4)	0.6478 (2)	1.04146 (6)	0.0449 (5)
H14A	0.9162	0.7354	1.0232	0.054*
H14B	0.7043	0.6329	1.0451	0.054*
C11	1.0022 (4)	0.3431 (2)	0.95472 (6)	0.0460 (5)
H11A	1.1899	0.3581	0.9514	0.055*
H11B	0.9768	0.2548	0.9727	0.055*
C13	1.0049 (4)	0.5109 (2)	1.01967 (6)	0.0452 (5)
H13A	1.1928	0.5251	1.0164	0.054*
H13B	0.9782	0.4230	1.0378	0.054*
C8	0.8741 (4)	0.1408 (2)	0.84769 (6)	0.0446 (5)
H8A	0.9004	0.2272	0.8290	0.053*
H8B	0.6864	0.1277	0.8516	0.053*
C9	0.9971 (4)	0.1740 (2)	0.89002 (6)	0.0473 (5)
H9A	1.1843	0.1888	0.8860	0.057*
H9B	0.9737	0.0868	0.9085	0.057*
C15	1.0109 (5)	0.6806 (2)	1.08385 (7)	0.0525 (6)
H15A	1.1985	0.6949	1.0803	0.063*
H15B	0.9853	0.5934	1.1022	0.063*
C1	0.8662 (4)	−0.0286 (2)	0.78391 (6)	0.0453 (5)
C16	0.8981 (6)	0.8184 (3)	1.10536 (7)	0.0654 (7)
H16A	0.9830	0.8331	1.1324	0.098*
H16B	0.7130	0.8042	1.1097	0.098*
H16C	0.9263	0.9058	1.0877	0.098*
C7	0.9847 (4)	0.0006 (2)	0.82643 (7)	0.0556 (6)
H7A	1.1731	0.0123	0.8232	0.067*
H7B	0.9538	−0.0864	0.8447	0.067*
C3	0.5427 (5)	−0.1466 (3)	0.74008 (9)	0.0661 (7)
H3A	0.3990	−0.2111	0.7374	0.079*
C2	0.6538 (5)	−0.1234 (3)	0.77901 (8)	0.0565 (6)
H2A	0.5848	−0.1726	0.8027	0.068*
C5	0.8497 (5)	0.0174 (3)	0.70955 (8)	0.0655 (7)
H5A	0.9171	0.0662	0.6856	0.079*
C6	0.9616 (5)	0.0406 (3)	0.74830 (8)	0.0586 (6)
H6A	1.1059	0.1049	0.7506	0.070*
C4	0.6412 (6)	−0.0762 (3)	0.70546 (9)	0.0666 (7)
H4A	0.5657	−0.0919	0.6788	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C12	0.0471 (11)	0.0471 (12)	0.0427 (12)	0.0013 (10)	−0.0018 (10)	0.0029 (10)
C10	0.0488 (11)	0.0475 (12)	0.0417 (12)	0.0025 (10)	−0.0021 (10)	0.0032 (10)
C14	0.0481 (11)	0.0472 (12)	0.0394 (12)	0.0012 (10)	0.0004 (10)	0.0047 (10)
C11	0.0475 (10)	0.0479 (11)	0.0425 (12)	−0.0005 (10)	−0.0021 (10)	0.0021 (10)
C13	0.0458 (11)	0.0463 (12)	0.0434 (13)	0.0006 (10)	−0.0035 (10)	0.0026 (10)
C8	0.0452 (10)	0.0480 (12)	0.0406 (12)	0.0029 (10)	−0.0003 (9)	0.0025 (10)
C9	0.0462 (10)	0.0510 (13)	0.0445 (13)	0.0051 (10)	−0.0029 (10)	0.0011 (10)
C15	0.0627 (13)	0.0520 (13)	0.0429 (13)	−0.0006 (12)	−0.0016 (12)	0.0019 (11)
C1	0.0450 (10)	0.0461 (11)	0.0449 (13)	0.0108 (10)	−0.0006 (10)	−0.0025 (10)
C16	0.0881 (19)	0.0601 (16)	0.0479 (15)	−0.0008 (15)	0.0045 (14)	−0.0050 (11)
C7	0.0556 (12)	0.0647 (15)	0.0465 (14)	0.0153 (12)	−0.0040 (11)	−0.0036 (12)
C3	0.0572 (14)	0.0635 (16)	0.0777 (19)	−0.0034 (13)	−0.0145 (14)	−0.0076 (15)
C2	0.0532 (12)	0.0575 (14)	0.0590 (16)	0.0033 (12)	0.0051 (12)	0.0030 (12)
C5	0.0704 (15)	0.0778 (17)	0.0484 (15)	0.0054 (15)	0.0001 (13)	0.0053 (13)
C6	0.0532 (12)	0.0664 (15)	0.0563 (15)	−0.0059 (12)	−0.0012 (11)	−0.0013 (12)
C4	0.0704 (16)	0.0701 (16)	0.0594 (17)	0.0132 (15)	−0.0152 (14)	−0.0114 (14)

Geometric parameters (Å, º)

C12—C13	1.511 (3)	C9—H9B	0.9800
C12—C11	1.521 (3)	C15—C16	1.519 (3)
C12—H12A	0.9800	C15—H15A	0.9800
C12—H12B	0.9800	C15—H15B	0.9800
C10—C11	1.515 (3)	C1—C6	1.376 (3)
C10—C9	1.523 (3)	C1—C2	1.389 (3)
C10—H10A	0.9800	C1—C7	1.501 (3)
C10—H10B	0.9800	C16—H16A	0.9700
C14—C15	1.505 (3)	C16—H16B	0.9700
C14—C13	1.518 (3)	C16—H16C	0.9700
C14—H14A	0.9800	C7—H7A	0.9800
C14—H14B	0.9800	C7—H7B	0.9800
C11—H11A	0.9800	C3—C4	1.362 (3)
C11—H11B	0.9800	C3—C2	1.375 (3)
C13—H13A	0.9800	C3—H3A	0.9400
C13—H13B	0.9800	C2—H2A	0.9400
C8—C9	1.512 (3)	C5—C4	1.364 (4)
C8—C7	1.529 (3)	C5—C6	1.372 (3)
C8—H8A	0.9800	C5—H5A	0.9400
C8—H8B	0.9800	C6—H6A	0.9400
C9—H9A	0.9800	C4—H4A	0.9400
C13—C12—C11	114.05 (17)	C8—C9—H9B	108.8
C13—C12—H12A	108.7	C10—C9—H9B	108.8
C11—C12—H12A	108.7	H9A—C9—H9B	107.7
C13—C12—H12B	108.7	C14—C15—C16	113.7 (2)
C11—C12—H12B	108.7	C14—C15—H15A	108.8
H12A—C12—H12B	107.6	C16—C15—H15A	108.8
C11—C10—C9	113.74 (17)	C14—C15—H15B	108.8
C11—C10—H10A	108.8	C16—C15—H15B	108.8
C9—C10—H10A	108.8	H15A—C15—H15B	107.7
C11—C10—H10B	108.8	C6—C1—C2	117.4 (2)
C9—C10—H10B	108.8	C6—C1—C7	120.9 (2)
H10A—C10—H10B	107.7	C2—C1—C7	121.6 (2)
C15—C14—C13	113.95 (17)	C15—C16—H16A	109.5
C15—C14—H14A	108.8	C15—C16—H16B	109.5
C13—C14—H14A	108.8	H16A—C16—H16B	109.5
C15—C14—H14B	108.8	C15—C16—H16C	109.5
C13—C14—H14B	108.8	H16A—C16—H16C	109.5
H14A—C14—H14B	107.7	H16B—C16—H16C	109.5
C10—C11—C12	113.93 (17)	C1—C7—C8	112.70 (17)
C10—C11—H11A	108.8	C1—C7—H7A	109.1
C12—C11—H11A	108.8	C8—C7—H7A	109.1
C10—C11—H11B	108.8	C1—C7—H7B	109.1
C12—C11—H11B	108.8	C8—C7—H7B	109.1
H11A—C11—H11B	107.7	H7A—C7—H7B	107.8
C12—C13—C14	113.87 (17)	C4—C3—C2	119.9 (2)
C12—C13—H13A	108.8	C4—C3—H3A	120.0
C14—C13—H13A	108.8	C2—C3—H3A	120.0
C12—C13—H13B	108.8	C3—C2—C1	121.2 (2)
C14—C13—H13B	108.8	C3—C2—H2A	119.4
H13A—C13—H13B	107.7	C1—C2—H2A	119.4
C9—C8—C7	113.28 (18)	C4—C5—C6	120.5 (2)
C9—C8—H8A	108.9	C4—C5—H5A	119.8
C7—C8—H8A	108.9	C6—C5—H5A	119.8
C9—C8—H8B	108.9	C5—C6—C1	121.1 (2)
C7—C8—H8B	108.9	C5—C6—H6A	119.4
H8A—C8—H8B	107.7	C1—C6—H6A	119.4
C8—C9—C10	113.60 (18)	C3—C4—C5	119.8 (2)
C8—C9—H9A	108.8	C3—C4—H4A	120.1
C10—C9—H9A	108.8	C5—C4—H4A	120.1