(S,S)-N-Cyclo­hexyl-3,4-di­hydroxy­pyrrolidine

The title compound, C₁₀H₁₉NO₂, has two symmetry-independent mol­ecules in the asymmetric unit with almost identical geometry. The pyrrolidine rings have envelope conformations and the cyclo­hexyl rings slightly distorted chair conformations. The mol­ecules are joined by hydrogen bonds, via the hydroxyl groups, in zigzag chains running along the [101] direction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.040
• wR factor = 0.097
• Data-to-parameter ratio = 8.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           72.40
         From the CIF: _reflns_number_total               2126
         Count of symmetry unique reflns         2135
         Completeness (_total/calc)             99.58%
         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.

---

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97.

(S,S)—N-cyclohexyl-3,4-dihydroxypyrrolidine

Crystal data

C10H19NO2	F(000) = 408
Mr = 185.26	Dx = 1.170 Mg m^−3
Monoclinic, P21	Melting point: 398 K
Hall symbol: P 2yb	Cu Kα radiation, λ = 1.54180 Å
a = 6.605 (5) Å	Cell parameters from 25 reflections
b = 25.230 (8) Å	θ = 18.3–31.5°
c = 6.870 (5) Å	µ = 0.64 mm^−1
β = 113.22 (5)°	T = 293 K
V = 1052.1 (12) Å^3	Block, white
Z = 4	0.42 × 0.40 × 0.36 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	1928 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.098
Graphite monochromator	θmax = 72.4°, θmin = 3.5°
profile data from w–2θ scans	h = −8→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→31
Tmin = 0.719, Tmax = 0.791	l = −8→7
6050 measured reflections	3 standard reflections every 180 min
2126 independent reflections	intensity decay: 10.2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0287P)^2 + 0.0651P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2126 reflections	Δρmax = 0.14 e Å^−3
239 parameters	Δρmin = −0.19 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.1 (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
O1	0.3499 (3)	0.21900 (9)	0.0892 (2)	0.0582 (5)
H1	0.2505	0.1980	0.0277	0.087*
O2	0.2895 (3)	0.15392 (7)	0.5112 (3)	0.0574 (5)
H2	0.2059	0.1347	0.4177	0.086*
N1	0.6370 (3)	0.24880 (7)	0.6349 (3)	0.0392 (4)
C2	0.6249 (4)	0.24566 (12)	0.4155 (4)	0.0490 (6)
H2A	0.7664	0.2353	0.4155	0.059*
H2B	0.5837	0.2797	0.3455	0.059*
C3	0.4534 (4)	0.20473 (9)	0.3047 (3)	0.0435 (5)
H3A	0.5233	0.1699	0.3172	0.052*
C4	0.2998 (4)	0.20452 (9)	0.4254 (3)	0.0415 (5)
H4	0.1517	0.2163	0.3321	0.050*
C5	0.4021 (4)	0.24361 (10)	0.6028 (4)	0.0433 (5)
H5A	0.3284	0.2776	0.5657	0.052*
H5B	0.3903	0.2309	0.7312	0.052*
C6	0.7334 (4)	0.29838 (9)	0.7424 (4)	0.0434 (5)
H6	0.6403	0.3277	0.6628	0.052*
C7	0.7374 (5)	0.29907 (11)	0.9667 (4)	0.0568 (6)
H7A	0.5883	0.2953	0.9590	0.068*
H7B	0.8227	0.2691	1.0456	0.068*
C8	0.8366 (6)	0.34994 (14)	1.0829 (6)	0.0766 (9)
H8A	0.7452	0.3797	1.0101	0.092*
H8B	0.8396	0.3485	1.2251	0.092*
C9	1.0666 (7)	0.35813 (16)	1.0947 (7)	0.0894 (11)
H9A	1.1618	0.3302	1.1792	0.107*
H9B	1.1233	0.3918	1.1629	0.107*
C10	1.0680 (5)	0.35771 (14)	0.8734 (6)	0.0777 (9)
H10A	1.2186	0.3607	0.8847	0.093*
H10B	0.9870	0.3882	0.7952	0.093*
C11	0.9649 (4)	0.30716 (11)	0.7512 (5)	0.0576 (6)
H11A	0.9590	0.3097	0.6082	0.069*
H11B	1.0565	0.2770	0.8193	0.069*
O1'	−0.5226 (2)	0.10920 (9)	−0.0907 (3)	0.0625 (5)
H1'	−0.5737	0.1236	−0.2071	0.094*
O2'	−0.0557 (3)	0.16886 (8)	−0.1205 (3)	0.0583 (5)
H2'	−0.1472	0.1898	−0.1973	0.088*
N1'	0.0304 (3)	0.07780 (7)	0.2200 (3)	0.0380 (4)
C2'	−0.1987 (3)	0.08547 (10)	0.1973 (3)	0.0468 (5)
H2A'	−0.2025	0.0996	0.3271	0.056*
H2B'	−0.2778	0.0521	0.1654	0.056*
C3'	−0.3018 (3)	0.12441 (9)	0.0163 (3)	0.0412 (5)
H3A'	−0.2941	0.1604	0.0722	0.049*
C4'	−0.1600 (3)	0.12041 (9)	−0.1149 (3)	0.0420 (5)
H4'	−0.2508	0.1088	−0.2593	0.050*
C5'	0.0108 (4)	0.07859 (10)	−0.0028 (4)	0.0433 (5)
H5A'	−0.0358	0.0442	−0.0685	0.052*
H5B'	0.1511	0.0875	−0.0088	0.052*
C6'	0.1233 (3)	0.02761 (9)	0.3261 (4)	0.0424 (5)
H6'	0.0375	−0.0016	0.2379	0.051*
C7'	0.3621 (4)	0.02143 (11)	0.3519 (5)	0.0571 (7)
H7A'	0.3689	0.0216	0.2134	0.069*
H7B'	0.4475	0.0513	0.4317	0.069*
C8'	0.4622 (5)	−0.02989 (15)	0.4662 (8)	0.0801 (10)
H8A'	0.3859	−0.0598	0.3798	0.096*
H8B'	0.6157	−0.0318	0.4859	0.096*
C9'	0.4458 (6)	−0.03320 (16)	0.6799 (7)	0.0886 (11)
H9A'	0.5028	−0.0671	0.7451	0.106*
H9B'	0.5350	−0.0055	0.7717	0.106*
C10'	0.2103 (6)	−0.02722 (13)	0.6571 (5)	0.0725 (8)
H10C	0.2053	−0.0274	0.7963	0.087*
H10D	0.1244	−0.0571	0.5780	0.087*
C11'	0.1101 (4)	0.02384 (10)	0.5440 (4)	0.0534 (6)
H11C	0.1870	0.0537	0.6303	0.064*
H11D	−0.0430	0.0257	0.5261	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0695 (11)	0.0713 (12)	0.0356 (8)	−0.0155 (9)	0.0229 (8)	0.0005 (8)
O2	0.0819 (12)	0.0496 (10)	0.0386 (8)	−0.0190 (9)	0.0214 (9)	0.0011 (7)
N1	0.0405 (9)	0.0450 (10)	0.0356 (9)	−0.0006 (7)	0.0188 (8)	0.0013 (8)
C2	0.0438 (11)	0.0700 (15)	0.0393 (11)	−0.0030 (11)	0.0228 (10)	0.0015 (11)
C3	0.0497 (12)	0.0511 (13)	0.0343 (10)	0.0068 (9)	0.0215 (10)	0.0031 (9)
C4	0.0437 (11)	0.0468 (12)	0.0373 (10)	0.0010 (9)	0.0194 (10)	0.0060 (9)
C5	0.0456 (12)	0.0477 (12)	0.0455 (12)	−0.0016 (10)	0.0276 (11)	−0.0020 (10)
C6	0.0456 (12)	0.0407 (12)	0.0455 (11)	−0.0006 (9)	0.0196 (10)	0.0043 (10)
C7	0.0738 (16)	0.0498 (15)	0.0507 (13)	−0.0130 (13)	0.0288 (13)	−0.0097 (12)
C8	0.104 (2)	0.0591 (18)	0.0683 (19)	−0.0223 (16)	0.0357 (19)	−0.0218 (16)
C9	0.091 (2)	0.068 (2)	0.089 (3)	−0.0260 (18)	0.014 (2)	−0.0167 (19)
C10	0.0583 (16)	0.0649 (19)	0.100 (3)	−0.0179 (14)	0.0206 (18)	0.0073 (18)
C11	0.0457 (13)	0.0609 (17)	0.0644 (15)	−0.0049 (11)	0.0199 (13)	0.0062 (13)
O1'	0.0386 (8)	0.0881 (14)	0.0581 (10)	−0.0059 (8)	0.0163 (8)	0.0198 (10)
O2'	0.0485 (9)	0.0549 (11)	0.0740 (12)	−0.0007 (7)	0.0267 (9)	0.0216 (9)
N1'	0.0386 (9)	0.0422 (9)	0.0364 (8)	0.0007 (7)	0.0182 (8)	0.0021 (8)
C2'	0.0426 (11)	0.0629 (15)	0.0419 (10)	0.0071 (10)	0.0242 (10)	0.0090 (11)
C3'	0.0362 (10)	0.0478 (12)	0.0417 (10)	−0.0001 (9)	0.0176 (9)	0.0016 (9)
C4'	0.0443 (10)	0.0483 (12)	0.0379 (10)	−0.0059 (9)	0.0212 (9)	−0.0007 (9)
C5'	0.0486 (11)	0.0485 (13)	0.0411 (10)	0.0015 (10)	0.0266 (10)	−0.0003 (10)
C6'	0.0409 (10)	0.0382 (11)	0.0467 (11)	−0.0025 (9)	0.0159 (10)	−0.0005 (9)
C7'	0.0445 (13)	0.0546 (16)	0.0744 (18)	0.0064 (11)	0.0256 (14)	0.0075 (13)
C8'	0.0596 (18)	0.0613 (19)	0.119 (3)	0.0186 (13)	0.034 (2)	0.0180 (19)
C9'	0.080 (2)	0.071 (2)	0.096 (3)	0.0264 (17)	0.015 (2)	0.0310 (19)
C10'	0.091 (2)	0.0596 (17)	0.0673 (18)	0.0086 (14)	0.0312 (18)	0.0241 (14)
C11'	0.0621 (14)	0.0507 (14)	0.0484 (12)	0.0024 (12)	0.0229 (12)	0.0102 (12)

Geometric parameters (Å, º)

O1—C3	1.411 (3)	O1'—C3'	1.403 (3)
O1—H1	0.8200	O1'—H1'	0.8200
O2—C4	1.419 (3)	O2'—C4'	1.411 (3)
O2—H2	0.8200	O2'—H2'	0.8200
N1—C6	1.465 (3)	N1'—C6'	1.469 (3)
N1—C2	1.480 (3)	N1'—C2'	1.472 (3)
N1—C5	1.484 (3)	N1'—C5'	1.485 (3)
C2—C3	1.500 (4)	C2'—C3'	1.519 (3)
C2—H2A	0.9700	C2'—H2A'	0.9700
C2—H2B	0.9700	C2'—H2B'	0.9700
C3—C4	1.543 (3)	C3'—C4'	1.538 (3)
C3—H3A	0.9800	C3'—H3A'	0.9800
C4—C5	1.505 (3)	C4'—C5'	1.515 (4)
C4—H4	0.9800	C4'—H4'	0.9800
C5—H5A	0.9700	C5'—H5A'	0.9700
C5—H5B	0.9700	C5'—H5B'	0.9700
C6—C11	1.522 (3)	C6'—C7'	1.525 (3)
C6—C7	1.531 (3)	C6'—C11'	1.536 (3)
C6—H6	0.9800	C6'—H6'	0.9800
C7—C8	1.517 (4)	C7'—C8'	1.523 (4)
C7—H7A	0.9700	C7'—H7A'	0.9700
C7—H7B	0.9700	C7'—H7B'	0.9700
C8—C9	1.504 (5)	C8'—C9'	1.517 (6)
C8—H8A	0.9700	C8'—H8A'	0.9700
C8—H8B	0.9700	C8'—H8B'	0.9700
C9—C10	1.524 (5)	C9'—C10'	1.508 (5)
C9—H9A	0.9700	C9'—H9A'	0.9700
C9—H9B	0.9700	C9'—H9B'	0.9700
C10—C11	1.531 (4)	C10'—C11'	1.515 (4)
C10—H10A	0.9700	C10'—H10C	0.9700
C10—H10B	0.9700	C10'—H10D	0.9700
C11—H11A	0.9700	C11'—H11C	0.9700
C11—H11B	0.9700	C11'—H11D	0.9700
C3—O1—H1	109.5	C3'—O1'—H1'	109.5
C4—O2—H2	109.5	C4'—O2'—H2'	109.5
C6—N1—C2	113.40 (17)	C6'—N1'—C2'	112.13 (16)
C6—N1—C5	111.82 (16)	C6'—N1'—C5'	111.88 (17)
C2—N1—C5	102.17 (18)	C2'—N1'—C5'	102.76 (17)
N1—C2—C3	106.27 (17)	N1'—C2'—C3'	106.37 (16)
N1—C2—H2A	110.5	N1'—C2'—H2A'	110.5
C3—C2—H2A	110.5	C3'—C2'—H2A'	110.5
N1—C2—H2B	110.5	N1'—C2'—H2B'	110.5
C3—C2—H2B	110.5	C3'—C2'—H2B'	110.5
H2A—C2—H2B	108.7	H2A'—C2'—H2B'	108.6
O1—C3—C2	108.3 (2)	O1'—C3'—C2'	106.85 (19)
O1—C3—C4	114.5 (2)	O1'—C3'—C4'	114.97 (18)
C2—C3—C4	104.77 (17)	C2'—C3'—C4'	104.93 (17)
O1—C3—H3A	109.7	O1'—C3'—H3A'	110.0
C2—C3—H3A	109.7	C2'—C3'—H3A'	110.0
C4—C3—H3A	109.7	C4'—C3'—H3A'	110.0
O2—C4—C5	109.46 (18)	O2'—C4'—C5'	110.10 (18)
O2—C4—C3	112.04 (18)	O2'—C4'—C3'	112.05 (19)
C5—C4—C3	104.60 (18)	C5'—C4'—C3'	104.54 (17)
O2—C4—H4	110.2	O2'—C4'—H4'	110.0
C5—C4—H4	110.2	C5'—C4'—H4'	110.0
C3—C4—H4	110.2	C3'—C4'—H4'	110.0
N1—C5—C4	106.73 (16)	N1'—C5'—C4'	106.17 (17)
N1—C5—H5A	110.4	N1'—C5'—H5A'	110.5
C4—C5—H5A	110.4	C4'—C5'—H5A'	110.5
N1—C5—H5B	110.4	N1'—C5'—H5B'	110.5
C4—C5—H5B	110.4	C4'—C5'—H5B'	110.5
H5A—C5—H5B	108.6	H5A'—C5'—H5B'	108.7
N1—C6—C11	112.00 (19)	N1'—C6'—C7'	110.89 (18)
N1—C6—C7	110.40 (17)	N1'—C6'—C11'	111.33 (18)
C11—C6—C7	109.9 (2)	C7'—C6'—C11'	109.5 (2)
N1—C6—H6	108.1	N1'—C6'—H6'	108.3
C11—C6—H6	108.1	C7'—C6'—H6'	108.3
C7—C6—H6	108.1	C11'—C6'—H6'	108.3
C8—C7—C6	111.8 (2)	C8'—C7'—C6'	111.5 (2)
C8—C7—H7A	109.3	C8'—C7'—H7A'	109.3
C6—C7—H7A	109.3	C6'—C7'—H7A'	109.3
C8—C7—H7B	109.3	C8'—C7'—H7B'	109.3
C6—C7—H7B	109.3	C6'—C7'—H7B'	109.3
H7A—C7—H7B	107.9	H7A'—C7'—H7B'	108.0
C9—C8—C7	111.2 (3)	C9'—C8'—C7'	111.3 (3)
C9—C8—H8A	109.4	C9'—C8'—H8A'	109.4
C7—C8—H8A	109.4	C7'—C8'—H8A'	109.4
C9—C8—H8B	109.4	C9'—C8'—H8B'	109.4
C7—C8—H8B	109.4	C7'—C8'—H8B'	109.4
H8A—C8—H8B	108.0	H8A'—C8'—H8B'	108.0
C8—C9—C10	110.4 (3)	C10'—C9'—C8'	111.0 (3)
C8—C9—H9A	109.6	C10'—C9'—H9A'	109.4
C10—C9—H9A	109.6	C8'—C9'—H9A'	109.4
C8—C9—H9B	109.6	C10'—C9'—H9B'	109.4
C10—C9—H9B	109.6	C8'—C9'—H9B'	109.4
H9A—C9—H9B	108.1	H9A'—C9'—H9B'	108.0
C9—C10—C11	112.1 (3)	C9'—C10'—C11'	111.2 (3)
C9—C10—H10A	109.2	C9'—C10'—H10C	109.4
C11—C10—H10A	109.2	C11'—C10'—H10C	109.4
C9—C10—H10B	109.2	C9'—C10'—H10D	109.4
C11—C10—H10B	109.2	C11'—C10'—H10D	109.4
H10A—C10—H10B	107.9	H10C—C10'—H10D	108.0
C6—C11—C10	111.4 (2)	C10'—C11'—C6'	111.8 (2)
C6—C11—H11A	109.3	C10'—C11'—H11C	109.3
C10—C11—H11A	109.3	C6'—C11'—H11C	109.3
C6—C11—H11B	109.3	C10'—C11'—H11D	109.3
C10—C11—H11B	109.3	C6'—C11'—H11D	109.3
H11A—C11—H11B	108.0	H11C—C11'—H11D	107.9
C6—N1—C2—C3	−159.30 (19)	C6'—N1'—C2'—C3'	−157.66 (18)
C5—N1—C2—C3	−38.8 (2)	C5'—N1'—C2'—C3'	−37.4 (2)
N1—C2—C3—O1	148.41 (18)	N1'—C2'—C3'—O1'	144.85 (19)
N1—C2—C3—C4	25.8 (2)	N1'—C2'—C3'—C4'	22.4 (2)
O1—C3—C4—O2	120.4 (2)	O1'—C3'—C4'—O2'	125.0 (2)
C2—C3—C4—O2	−121.1 (2)	C2'—C3'—C4'—O2'	−117.9 (2)
O1—C3—C4—C5	−121.1 (2)	O1'—C3'—C4'—C5'	−115.8 (2)
C2—C3—C4—C5	−2.6 (2)	C2'—C3'—C4'—C5'	1.3 (2)
C6—N1—C5—C4	158.68 (18)	C6'—N1'—C5'—C4'	158.73 (17)
C2—N1—C5—C4	37.1 (2)	C2'—N1'—C5'—C4'	38.3 (2)
O2—C4—C5—N1	98.9 (2)	O2'—C4'—C5'—N1'	96.3 (2)
C3—C4—C5—N1	−21.3 (2)	C3'—C4'—C5'—N1'	−24.3 (2)
C2—N1—C6—C11	−58.0 (2)	C2'—N1'—C6'—C7'	−178.7 (2)
C5—N1—C6—C11	−172.9 (2)	C5'—N1'—C6'—C7'	66.5 (3)
C2—N1—C6—C7	179.2 (2)	C2'—N1'—C6'—C11'	−56.5 (2)
C5—N1—C6—C7	64.3 (2)	C5'—N1'—C6'—C11'	−171.32 (19)
N1—C6—C7—C8	180.0 (2)	N1'—C6'—C7'—C8'	178.7 (3)
C11—C6—C7—C8	56.0 (3)	C11'—C6'—C7'—C8'	55.5 (3)
C6—C7—C8—C9	−57.7 (4)	C6'—C7'—C8'—C9'	−56.4 (4)
C7—C8—C9—C10	56.2 (4)	C7'—C8'—C9'—C10'	55.8 (4)
C8—C9—C10—C11	−55.1 (4)	C8'—C9'—C10'—C11'	−55.8 (4)
N1—C6—C11—C10	−177.2 (2)	C9'—C10'—C11'—C6'	56.4 (4)
C7—C6—C11—C10	−54.1 (3)	N1'—C6'—C11'—C10'	−178.7 (2)
C9—C10—C11—C6	54.7 (4)	C7'—C6'—C11'—C10'	−55.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2′	0.82	2.01	2.795 (3)	160
O2—H2···N1′	0.82	2.00	2.814 (3)	170
O1′—H1′···O2^i	0.82	1.94	2.760 (3)	176
O2′—H2′···N1^i	0.82	2.07	2.885 (3)	174

Symmetry code: (i) x−1, y, z−1.