[4-(4-Meth-oxy-phen-yl)-1-methyl-3-nitro-pyrrolidin-3-yl]methanol.

In the title compound, C13H18N2O4, the dihedral angle between the benzene and pyrrolidine (all atoms) rings is 70.6 (1)°. The pyrrolidine ring adopts a half-chair conformation. In the crystal, mol-ecules form chains along the c-axis direction linked by O-H⋯N hydrogen bonds, which are then connected by C-H⋯O inter-actions, forming a sheet parallel to the bc plane.

Related literature

For information on the pyrrolidine ring in biologically active natural compounds, see: Gu et al. (2004 ▶). For the use of pyrrolidine-containing mol­ecules in the treatment of diseases, see, for example: Horri et al. (1986 ▶) for diabetes and Karpas et al. (1988 ▶) for viral infections. For bond lengths in a related structure, see: Jayabharathi et al. (2009 ▶).

Experimental

Crystal data

C13H18N2O4

M = 266.29

Monoclinic,

a = 11.6827 (10) Å

b = 11.1912 (11) Å

c = 11.1789 (11) Å

β = 109.118 (2)°

V = 1381.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.22 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

12464 measured reflections

3407 independent reflections

2282 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.162

S = 1.01

3407 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813003073/nk2193sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003073/nk2193Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003073/nk2193Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H18N2O4	F(000) = 568
Mr = 266.29	Dx = 1.281 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3407 reflections
a = 11.6827 (10) Å	θ = 1.5–28.3°
b = 11.1912 (11) Å	µ = 0.10 mm−1
c = 11.1789 (11) Å	T = 293 K
β = 109.118 (2)°	Block, colourless
V = 1381.0 (2) Å3	0.22 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2282 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 28.3°, θmin = 1.8°
ω and φ scan	h = −15→15
12464 measured reflections	k = −14→14
3407 independent reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
3407 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	−0.36799 (16)	0.15244 (19)	0.51274 (18)	0.0686 (5)
H1A	−0.4468	0.1772	0.4592	0.103*
H1B	−0.3743	0.0770	0.5509	0.103*
H1C	−0.3151	0.1445	0.4631	0.103*
C2	−0.20810 (13)	0.21887 (15)	0.69433 (15)	0.0481 (4)
C3	−0.13157 (13)	0.12749 (15)	0.68781 (14)	0.0487 (4)
H3	−0.1540	0.0751	0.6195	0.058*
C4	−0.02079 (13)	0.11333 (14)	0.78317 (14)	0.0451 (4)
H4	0.0301	0.0513	0.7772	0.054*
C5	0.01580 (12)	0.18913 (13)	0.88680 (13)	0.0397 (3)
C6	−0.06274 (14)	0.28269 (16)	0.88911 (16)	0.0544 (4)
H6	−0.0407	0.3355	0.9571	0.065*
C7	−0.17096 (15)	0.29922 (17)	0.79468 (17)	0.0589 (5)
H7	−0.2197	0.3641	0.7976	0.071*
C8	0.13415 (12)	0.17615 (13)	0.99434 (12)	0.0388 (3)
H8	0.1198	0.2054	1.0708	0.047*
C9	0.24446 (12)	0.24842 (13)	0.98146 (12)	0.0380 (3)
C10	0.22476 (13)	0.29756 (15)	0.84980 (13)	0.0443 (4)
H10A	0.2056	0.2330	0.7885	0.053*
H10B	0.1576	0.3535	0.8270	0.053*
C11	0.35084 (14)	0.16266 (15)	1.02668 (14)	0.0484 (4)
H11A	0.3672	0.1256	0.9555	0.058*
H11B	0.4232	0.2039	1.0783	0.058*
C12	0.38953 (16)	−0.03316 (17)	1.12644 (17)	0.0643 (5)
H12A	0.4701	−0.0119	1.1783	0.096*
H12B	0.3916	−0.0659	1.0478	0.096*
H12C	0.3573	−0.0915	1.1697	0.096*
C13	0.18708 (14)	0.05085 (15)	1.02428 (15)	0.0481 (4)
H13A	0.1451	0.0054	1.0711	0.058*
H13B	0.1826	0.0079	0.9475	0.058*
N1	0.31240 (11)	0.07359 (12)	1.10121 (11)	0.0433 (3)
N3	0.26471 (14)	0.35622 (12)	1.07021 (12)	0.0509 (4)
O1	−0.32042 (10)	0.23895 (12)	0.60855 (13)	0.0663 (4)
O2	0.33114 (10)	0.35553 (12)	0.84933 (10)	0.0578 (4)
H2	0.3213	0.3832	0.7788	0.087*
O3	0.18039 (14)	0.42471 (12)	1.05376 (14)	0.0740 (4)
O4	0.36032 (15)	0.36987 (16)	1.15196 (15)	0.1019 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0467 (9)	0.0815 (14)	0.0648 (12)	0.0034 (9)	0.0006 (8)	−0.0089 (10)
C2	0.0367 (7)	0.0534 (10)	0.0510 (9)	−0.0001 (7)	0.0101 (7)	0.0014 (7)
C3	0.0456 (8)	0.0500 (9)	0.0461 (8)	−0.0014 (7)	0.0091 (7)	−0.0101 (7)
C4	0.0396 (8)	0.0449 (9)	0.0480 (8)	0.0002 (6)	0.0107 (7)	−0.0060 (6)
C5	0.0366 (7)	0.0443 (8)	0.0403 (7)	−0.0048 (6)	0.0155 (6)	−0.0034 (6)
C6	0.0462 (9)	0.0618 (11)	0.0532 (9)	0.0018 (8)	0.0138 (7)	−0.0168 (8)
C7	0.0485 (9)	0.0589 (11)	0.0675 (11)	0.0111 (8)	0.0164 (9)	−0.0118 (8)
C8	0.0392 (7)	0.0449 (8)	0.0341 (7)	−0.0050 (6)	0.0147 (6)	−0.0028 (6)
C9	0.0385 (7)	0.0426 (8)	0.0312 (7)	−0.0060 (6)	0.0092 (6)	−0.0026 (5)
C10	0.0414 (8)	0.0549 (9)	0.0348 (7)	−0.0099 (7)	0.0098 (6)	0.0016 (6)
C11	0.0406 (8)	0.0611 (10)	0.0440 (8)	0.0002 (7)	0.0148 (7)	0.0069 (7)
C12	0.0694 (12)	0.0594 (12)	0.0626 (11)	0.0198 (9)	0.0196 (9)	0.0076 (8)
C13	0.0489 (8)	0.0451 (9)	0.0473 (8)	−0.0063 (7)	0.0116 (7)	0.0033 (6)
N1	0.0432 (7)	0.0483 (8)	0.0377 (6)	0.0036 (5)	0.0124 (5)	0.0043 (5)
N3	0.0627 (9)	0.0478 (8)	0.0384 (7)	−0.0138 (7)	0.0114 (6)	−0.0022 (6)
O1	0.0463 (7)	0.0686 (9)	0.0692 (8)	0.0104 (6)	−0.0013 (6)	−0.0085 (6)
O2	0.0480 (6)	0.0810 (9)	0.0414 (6)	−0.0216 (6)	0.0105 (5)	0.0112 (5)
O3	0.0861 (10)	0.0537 (8)	0.0824 (9)	0.0001 (7)	0.0281 (8)	−0.0176 (7)
O4	0.0916 (11)	0.0971 (12)	0.0788 (10)	−0.0172 (9)	−0.0244 (9)	−0.0309 (9)

C1—O1	1.415 (2)	C9—C10	1.5165 (19)
C1—H1A	0.9600	C9—C11	1.520 (2)
C1—H1B	0.9600	C9—N3	1.5303 (19)
C1—H1C	0.9600	C10—O2	1.4035 (17)
C2—O1	1.3666 (18)	C10—H10A	0.9700
C2—C3	1.376 (2)	C10—H10B	0.9700
C2—C7	1.392 (2)	C11—N1	1.4610 (19)
C3—C4	1.390 (2)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C5	1.386 (2)	C12—N1	1.467 (2)
C4—H4	0.9300	C12—H12A	0.9600
C5—C6	1.398 (2)	C12—H12B	0.9600
C5—C8	1.5130 (19)	C12—H12C	0.9600
C6—C7	1.369 (2)	C13—N1	1.4571 (19)
C6—H6	0.9300	C13—H13A	0.9700
C7—H7	0.9300	C13—H13B	0.9700
C8—C13	1.525 (2)	N3—O4	1.1989 (19)
C8—C9	1.5676 (18)	N3—O3	1.214 (2)
C8—H8	0.9800	O2—H2	0.8200
O1—C1—H1A	109.5	C11—C9—C8	104.53 (12)
O1—C1—H1B	109.5	N3—C9—C8	107.72 (11)
H1A—C1—H1B	109.5	O2—C10—C9	108.55 (11)
O1—C1—H1C	109.5	O2—C10—H10A	110.0
H1A—C1—H1C	109.5	C9—C10—H10A	110.0
H1B—C1—H1C	109.5	O2—C10—H10B	110.0
O1—C2—C3	125.19 (14)	C9—C10—H10B	110.0
O1—C2—C7	115.70 (14)	H10A—C10—H10B	108.4
C3—C2—C7	119.11 (14)	N1—C11—C9	104.48 (11)
C2—C3—C4	120.13 (14)	N1—C11—H11A	110.9
C2—C3—H3	119.9	C9—C11—H11A	110.9
C4—C3—H3	119.9	N1—C11—H11B	110.9
C5—C4—C3	121.74 (14)	C9—C11—H11B	110.9
C5—C4—H4	119.1	H11A—C11—H11B	108.9
C3—C4—H4	119.1	N1—C12—H12A	109.5
C4—C5—C6	116.70 (13)	N1—C12—H12B	109.5
C4—C5—C8	123.84 (13)	H12A—C12—H12B	109.5
C6—C5—C8	119.46 (13)	N1—C12—H12C	109.5
C7—C6—C5	122.22 (15)	H12A—C12—H12C	109.5
C7—C6—H6	118.9	H12B—C12—H12C	109.5
C5—C6—H6	118.9	N1—C13—C8	103.05 (12)
C6—C7—C2	119.99 (15)	N1—C13—H13A	111.2
C6—C7—H7	120.0	C8—C13—H13A	111.2
C2—C7—H7	120.0	N1—C13—H13B	111.2
C5—C8—C13	117.52 (12)	C8—C13—H13B	111.2
C5—C8—C9	116.25 (11)	H13A—C13—H13B	109.1
C13—C8—C9	102.02 (11)	C13—N1—C11	102.69 (11)
C5—C8—H8	106.8	C13—N1—C12	113.98 (14)
C13—C8—H8	106.8	C11—N1—C12	112.41 (12)
C9—C8—H8	106.8	O4—N3—O3	122.84 (16)
C10—C9—C11	113.55 (12)	O4—N3—C9	120.15 (15)
C10—C9—N3	106.59 (12)	O3—N3—C9	117.01 (13)
C11—C9—N3	110.26 (12)	C2—O1—C1	117.86 (14)
C10—C9—C8	114.09 (11)	C10—O2—H2	109.5
O1—C2—C3—C4	−177.74 (15)	C11—C9—C10—O2	−57.84 (17)
C7—C2—C3—C4	2.5 (2)	N3—C9—C10—O2	63.75 (15)
C2—C3—C4—C5	0.3 (2)	C8—C9—C10—O2	−177.49 (12)
C3—C4—C5—C6	−1.7 (2)	C10—C9—C11—N1	−144.62 (12)
C3—C4—C5—C8	178.72 (14)	N3—C9—C11—N1	95.86 (13)
C4—C5—C6—C7	0.4 (2)	C8—C9—C11—N1	−19.66 (14)
C8—C5—C6—C7	179.95 (16)	C5—C8—C13—N1	163.40 (11)
C5—C6—C7—C2	2.4 (3)	C9—C8—C13—N1	35.02 (13)
O1—C2—C7—C6	176.40 (16)	C8—C13—N1—C11	−48.96 (14)
C3—C2—C7—C6	−3.8 (3)	C8—C13—N1—C12	−170.81 (12)
C4—C5—C8—C13	−28.9 (2)	C9—C11—N1—C13	42.62 (14)
C6—C5—C8—C13	151.54 (15)	C9—C11—N1—C12	165.54 (13)
C4—C5—C8—C9	92.35 (17)	C10—C9—N3—O4	−115.56 (17)
C6—C5—C8—C9	−87.21 (17)	C11—C9—N3—O4	8.10 (19)
C5—C8—C9—C10	−13.76 (18)	C8—C9—N3—O4	121.60 (16)
C13—C8—C9—C10	115.42 (13)	C10—C9—N3—O3	64.81 (17)
C5—C8—C9—C11	−138.37 (12)	C11—C9—N3—O3	−171.52 (13)
C13—C8—C9—C11	−9.19 (13)	C8—C9—N3—O3	−58.03 (17)
C5—C8—C9—N3	104.35 (13)	C3—C2—O1—C1	7.2 (3)
C13—C8—C9—N3	−126.47 (12)	C7—C2—O1—C1	−173.08 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1i	0.82	2.01	2.8237 (16)	170
C1—H1A···O2ii	0.96	2.51	3.390 (2)	153
C3—H3···O3iii	0.93	2.51	3.429 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1i	0.82	2.01	2.8237 (16)	170
C1—H1A⋯O2ii	0.96	2.51	3.390 (2)	153
C3—H3⋯O3iii	0.93	2.51	3.429 (2)	171

Symmetry codes: (i) ; (ii) ; (iii) .