Nona­decane-1,19-diol

In the molecular structure of the title compound, C₁₉H₄₀O₂, one hydroxyl group adopts a gauche conformation with respect to the hydro­carbon skeleton which is all-trans, whereas the other hydroxyl group adopts a trans conformation. In the crystal, the mol­ecules lie parallel to the b axis, the longest axis, forming layers with thickness b/2 in which the long axis of the mol­ecule is normal to the layer plane. The packing is similar to that in the smectic A phase of liquid crystals. These features are similar to those of the homologues with an odd number of C atoms, but different from those with an even number of C atoms.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.137
• Data-to-parameter ratio = 10.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



ABSTM_02  Alert A Test not performed as the _exptl_absorpt_correction_type
          has not been identified. See test ABSTY_01.

ABSTY_01  Alert A The absorption correction should be one of the following
          *  none
          *  analytical
          *  integration
          *  numerical
          *  gaussian
          *  empirical
          *  psi-scan
          *  multi-scan
          *  refdelf
          *  sphere
          *  cylinder


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           70.58
         From the CIF: _reflns_number_total               2117
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         2237
         Completeness (_total/calc)             94.64%
          Alert C: < 95% complete

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           70.58
         From the CIF: _reflns_number_total               2117
         Count of symmetry unique reflns         2237
         Completeness (_total/calc)             94.64%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          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.


 2 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2000); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

(I)

Crystal data

C19H40O2	Dx = 1.034 Mg m^−3
Mr = 300.52	Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, P212121	Cell parameters from 22 reflections
a = 7.213 (5) Å	θ = 9.1–15.2°
b = 52.870 (3) Å	µ = 0.49 mm^−1
c = 5.061 (3) Å	T = 296 K
V = 1930 (1) Å^3	Plate, colorless
Z = 4	0.6 × 0.3 × 0.04 mm

Data collection

Rigaku AFC-5R diffractometer	Rint = 0.014
ω scans	θmax = 70.6°
Absorption correction: ψ (North et al., 1968)	h = −2→8
Tmin = 0.757, Tmax = 1.000	k = 0→64
3390 measured reflections	l = −1→5
2117 independent reflections	3 standard reflections every 150 reflections
1367 reflections with F^2 > 2σ(F^2)	intensity decay: 3.0%

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + {0.05[Max(Fo^2,0) + 2Fc^2]/3}^2]
R[F^2 > 2σ(F^2)] = 0.040	(Δ/σ)max = 0.001
wR(F^2) = 0.137	Δρmax = 0.09 e Å^−3
S = 1.42	Δρmin = −0.11 e Å^−3
2110 reflections	Extinction correction: Zachariasen (1967), type 2, Gaussian isotropic
197 parameters	Extinction coefficient: 0.043 (5)
H atoms treated by a mixture of independent and constrained refinement

Special details

Geometry. none

Refinement. Refinement using reflections with F² > -3.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
O1	1.0560 (3)	−0.23030 (3)	0.8589 (4)	0.0673 (5)
O2	1.0635 (3)	0.22552 (3)	0.4290 (4)	0.0753 (6)
C1	0.9980 (5)	−0.22781 (4)	0.5912 (6)	0.0716 (9)
C2	1.0529 (4)	−0.20292 (4)	0.4731 (5)	0.0614 (7)
C3	0.9668 (4)	−0.17984 (4)	0.6013 (5)	0.0528 (6)
C4	1.0383 (4)	−0.15524 (4)	0.4877 (5)	0.0532 (6)
C5	0.9582 (4)	−0.13159 (4)	0.6122 (5)	0.0514 (6)
C6	1.0362 (3)	−0.10725 (4)	0.4999 (5)	0.0516 (6)
C7	0.9584 (4)	−0.08339 (4)	0.6226 (5)	0.0519 (6)
C8	1.0380 (3)	−0.05920 (4)	0.5089 (5)	0.0516 (6)
C9	0.9591 (3)	−0.03524 (4)	0.6290 (5)	0.0522 (6)
C10	1.0394 (3)	−0.01113 (4)	0.5130 (5)	0.0509 (6)
C11	0.9597 (3)	0.01295 (4)	0.6297 (5)	0.0509 (6)
C12	1.0398 (3)	0.03697 (4)	0.5114 (5)	0.0506 (6)
C13	0.9594 (3)	0.06115 (3)	0.6264 (5)	0.0512 (6)
C14	1.0396 (4)	0.08501 (4)	0.5060 (5)	0.0511 (6)
C15	0.9590 (3)	0.10942 (4)	0.6160 (5)	0.0516 (6)
C16	1.0399 (4)	0.13306 (4)	0.4919 (5)	0.0519 (6)
C17	0.9605 (3)	0.15773 (4)	0.5962 (5)	0.0533 (6)
C18	1.0466 (4)	0.18074 (4)	0.4654 (5)	0.0555 (6)
C19	0.9709 (4)	0.20556 (4)	0.5639 (6)	0.0595 (7)
H1a	1.0528	−0.2410	0.4904	0.0859*
H1b	0.8668	−0.2293	0.5841	0.0859*
H1o	1.179 (4)	−0.2287 (5)	0.857 (6)	0.0809*
H2a	1.1838	−0.2014	0.4864	0.0737*
H2b	1.0179	−0.2030	0.2922	0.0737*
H2o	1.008 (4)	0.2390 (5)	0.484 (7)	0.0904*
H3a	0.8363	−0.1805	0.5763	0.0634*
H3b	0.9939	−0.1802	0.7850	0.0634*
H4a	1.1690	−0.1549	0.5105	0.0639*
H4b	1.0097	−0.1550	0.3045	0.0639*
H5a	0.8279	−0.1316	0.5850	0.0617*
H5b	0.9837	−0.1320	0.7963	0.0617*
H6a	1.1666	−0.1073	0.5265	0.0619*
H6b	1.0104	−0.1069	0.3159	0.0619*
H7a	0.8280	−0.0833	0.5956	0.0623*
H7b	0.9839	−0.0837	0.8067	0.0623*
H8a	1.1682	−0.0593	0.5375	0.0619*
H8b	1.0136	−0.0590	0.3245	0.0619*
H9a	0.8289	−0.0351	0.6010	0.0627*
H9b	0.9840	−0.0354	0.8133	0.0627*
H10a	1.1694	−0.0112	0.5428	0.0611*
H10b	1.0158	−0.0111	0.3283	0.0611*
H11a	0.8296	0.0130	0.6009	0.0611*
H11b	0.9840	0.0130	0.8142	0.0611*
H12a	1.1698	0.0370	0.5412	0.0607*
H12b	1.0162	0.0369	0.3267	0.0607*
H13a	0.8293	0.0611	0.5973	0.0614*
H13b	0.9835	0.0614	0.8109	0.0614*
H14a	1.1695	0.0851	0.5372	0.0614*
H14b	1.0170	0.0846	0.3211	0.0614*
H15a	0.8290	0.1094	0.5859	0.0619*
H15b	0.9823	0.1099	0.8007	0.0619*
H16a	1.1697	0.1331	0.5236	0.0623*
H16b	1.0176	0.1324	0.3071	0.0623*
H17a	0.8307	0.1579	0.5643	0.0639*
H17b	0.9827	0.1586	0.7810	0.0639*
H18a	1.1763	0.1804	0.4976	0.0666*
H18b	1.0245	0.1797	0.2807	0.0666*
H19a	0.9920	0.2070	0.7486	0.0715*
H19b	0.8416	0.2064	0.5296	0.0715*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.089 (1)	0.0447 (8)	0.068 (1)	−0.0057 (10)	−0.005 (1)	0.0044 (8)
O2	0.092 (1)	0.0371 (7)	0.097 (1)	0.0021 (9)	0.022 (1)	0.0010 (8)
C1	0.102 (2)	0.044 (1)	0.069 (2)	−0.004 (1)	−0.010 (2)	−0.008 (1)
C2	0.086 (2)	0.044 (1)	0.054 (1)	0.005 (1)	0.005 (2)	−0.0027 (10)
C3	0.060 (1)	0.0402 (9)	0.059 (1)	0.002 (1)	−0.001 (2)	−0.001 (1)
C4	0.057 (1)	0.043 (1)	0.060 (1)	0.002 (1)	0.003 (2)	0.0021 (10)
C5	0.055 (1)	0.0394 (9)	0.060 (1)	0.002 (1)	0.000 (2)	0.001 (1)
C6	0.053 (1)	0.0409 (10)	0.061 (1)	0.000 (1)	0.003 (2)	0.0032 (9)
C7	0.053 (1)	0.0402 (10)	0.062 (1)	0.002 (1)	0.000 (2)	0.002 (1)
C8	0.052 (1)	0.0389 (10)	0.064 (1)	0.002 (1)	0.004 (2)	0.0025 (9)
C9	0.053 (1)	0.0408 (10)	0.063 (1)	0.002 (1)	0.002 (2)	0.001 (1)
C10	0.053 (1)	0.0382 (9)	0.062 (1)	0.002 (1)	0.002 (1)	0.0003 (10)
C11	0.052 (1)	0.0399 (9)	0.061 (1)	0.003 (1)	0.002 (1)	0.001 (1)
C12	0.052 (1)	0.0391 (9)	0.061 (1)	0.001 (1)	0.001 (2)	0.0016 (9)
C13	0.052 (1)	0.0391 (9)	0.062 (1)	0.002 (1)	0.003 (2)	−0.001 (1)
C14	0.054 (1)	0.0383 (10)	0.061 (1)	−0.001 (1)	0.001 (2)	0.0011 (9)
C15	0.053 (1)	0.0403 (10)	0.062 (1)	0.002 (1)	0.004 (2)	−0.001 (1)
C16	0.055 (1)	0.0385 (9)	0.063 (1)	−0.002 (1)	0.002 (2)	−0.0008 (9)
C17	0.056 (1)	0.0398 (9)	0.064 (1)	0.003 (1)	0.001 (2)	−0.003 (1)
C18	0.060 (1)	0.0379 (9)	0.068 (2)	0.001 (1)	0.004 (2)	−0.0013 (10)
C19	0.064 (2)	0.0375 (9)	0.077 (2)	0.000 (1)	0.005 (2)	0.001 (1)

Geometric parameters (Å, º)

O1—C1	1.424 (3)	C9—C10	1.518 (3)
O2—C19	1.423 (3)	C10—C11	1.516 (3)
C1—C2	1.498 (3)	C11—C12	1.518 (3)
C2—C3	1.515 (3)	C12—C13	1.520 (3)
C3—C4	1.513 (3)	C13—C14	1.516 (3)
C4—C5	1.514 (3)	C14—C15	1.521 (3)
C5—C6	1.515 (3)	C15—C16	1.516 (3)
C6—C7	1.514 (3)	C16—C17	1.519 (3)
C7—C8	1.516 (3)	C17—C18	1.518 (3)
C8—C9	1.516 (3)	C18—C19	1.506 (3)
O1—C1—C2	112.5 (2)	C10—C11—C12	113.8 (2)
C1—C2—C3	115.3 (2)	C11—C12—C13	114.0 (2)
C2—C3—C4	112.9 (2)	C12—C13—C14	113.6 (2)
C3—C4—C5	114.9 (2)	C13—C14—C15	114.4 (2)
C4—C5—C6	113.8 (2)	C14—C15—C16	113.6 (2)
C5—C6—C7	114.6 (2)	C15—C16—C17	114.8 (2)
C6—C7—C8	114.0 (2)	C16—C17—C18	112.5 (2)
C7—C8—C9	114.2 (2)	C17—C18—C19	113.9 (2)
C8—C9—C10	113.8 (2)	O2—C19—C18	108.5 (2)
C9—C10—C11	114.2 (2)
O1—C1—C2—C3	−63.2 (4)	O2—C19—C18—C17	179.4 (2)