1-(4-Nitro­phen­yl)pyrrolidine-2-carboxamide

In the mol­ecule of the title compound, C₁₁H₁₃N₃O₃, the average plane of the pyrrolidine ring is roughly orthogonal to the plane of the carboxamide group and almost parallel to the benzene plane. The mol­ecules are linked via N—H...O hydrogen bonds into layers parallel to the ac plane.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.123
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.105
            Value of mu given      =     0.100
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-(4-Nitrophenyl)pyrrolidine-2-carboxamide

Crystal data

C11H13N3O3	F(000) = 992
Mr = 235.24	Dx = 1.407 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 52 reflections
a = 9.4711 (14) Å	θ = 2.3–18.9°
b = 13.1959 (16) Å	µ = 0.10 mm^−1
c = 17.773 (4) Å	T = 295 K
V = 2221.2 (6) Å^3	Prism, orange
Z = 8	0.6 × 0.4 × 0.3 mm

Data collection

Bruker P4 diffractometer	Rint = 0.032
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.3°
Graphite monochromator	h = −1→11
ω scans	k = −15→1
2508 measured reflections	l = −1→21
1915 independent reflections	3 standard reflections every 97 reflections
1083 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.001P)^2 + 2P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1915 reflections	Δρmax = 0.18 e Å^−3
155 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0066 (7)

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	0.7452 (2)	0.51362 (17)	0.76870 (13)	0.0749 (7)
O2	0.5309 (3)	0.8194 (2)	0.44972 (15)	0.0941 (9)
O3	0.7028 (3)	0.7566 (2)	0.38487 (15)	0.1018 (9)
N1	0.5211 (3)	0.52956 (19)	0.80850 (14)	0.0698 (8)
H1A	0.5375	0.5735	0.8463	0.084*
H1B	0.4276	0.5184	0.8052	0.084*
N2	0.6494 (3)	0.42434 (18)	0.63549 (13)	0.0600 (7)
N3	0.6188 (3)	0.7524 (2)	0.43813 (16)	0.0748 (8)
C1	0.6202 (3)	0.4928 (2)	0.76303 (17)	0.0571 (7)
C2	0.5670 (3)	0.4174 (2)	0.70433 (15)	0.0558 (7)
H2A	0.4666	0.4287	0.6938	0.067*
C3	0.5922 (4)	0.3079 (2)	0.73032 (19)	0.0720 (9)
H3A	0.5965	0.3042	0.7848	0.086*
H3B	0.5173	0.2638	0.7127	0.086*
C4	0.7302 (4)	0.2787 (3)	0.6963 (2)	0.0852 (11)
H4A	0.7318	0.2067	0.6854	0.102*
H4B	0.8070	0.2942	0.7305	0.102*
C5	0.7451 (3)	0.3387 (2)	0.62513 (18)	0.0676 (9)
H5A	0.8415	0.3617	0.6184	0.081*
H5B	0.7178	0.2986	0.5818	0.081*
C6	0.6415 (3)	0.5038 (2)	0.58735 (16)	0.0545 (7)
C7	0.7315 (3)	0.5109 (2)	0.52425 (16)	0.0652 (8)
H7A	0.7978	0.4602	0.5155	0.078*
C8	0.7229 (4)	0.5911 (2)	0.47584 (17)	0.0684 (9)
H8A	0.7832	0.5948	0.4346	0.082*
C9	0.6248 (3)	0.6664 (2)	0.48817 (17)	0.0608 (8)
C10	0.5344 (3)	0.6614 (2)	0.54885 (17)	0.0623 (8)
H10A	0.4685	0.7126	0.5564	0.075*
C11	0.5408 (3)	0.5818 (2)	0.59797 (16)	0.0590 (8)
H11A	0.4788	0.5789	0.6385	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0535 (13)	0.0836 (15)	0.0876 (15)	−0.0028 (11)	−0.0049 (12)	−0.0150 (13)
O2	0.109 (2)	0.0778 (17)	0.0958 (19)	0.0045 (16)	−0.0086 (17)	0.0215 (15)
O3	0.112 (2)	0.115 (2)	0.0776 (16)	−0.0166 (18)	0.0085 (17)	0.0248 (16)
N1	0.0652 (16)	0.0759 (18)	0.0683 (16)	0.0056 (14)	0.0043 (14)	−0.0201 (14)
N2	0.0662 (16)	0.0553 (14)	0.0586 (15)	0.0095 (13)	0.0055 (13)	−0.0024 (12)
N3	0.086 (2)	0.0769 (19)	0.0612 (17)	−0.0176 (18)	−0.0130 (17)	0.0071 (16)
C1	0.0575 (18)	0.0555 (17)	0.0581 (17)	0.0048 (15)	−0.0027 (15)	−0.0022 (15)
C2	0.0593 (17)	0.0531 (16)	0.0551 (16)	0.0012 (14)	0.0023 (14)	−0.0049 (14)
C3	0.082 (2)	0.0564 (18)	0.078 (2)	−0.0002 (17)	0.0032 (19)	0.0026 (17)
C4	0.086 (2)	0.068 (2)	0.102 (3)	0.0183 (19)	0.010 (2)	0.013 (2)
C5	0.067 (2)	0.0595 (18)	0.076 (2)	0.0108 (16)	0.0004 (18)	−0.0096 (17)
C6	0.0568 (17)	0.0555 (17)	0.0511 (16)	−0.0017 (14)	−0.0047 (14)	−0.0091 (14)
C7	0.069 (2)	0.0663 (19)	0.0606 (18)	0.0038 (16)	0.0086 (16)	−0.0080 (16)
C8	0.076 (2)	0.074 (2)	0.0558 (18)	−0.0118 (18)	0.0061 (17)	−0.0050 (17)
C9	0.0688 (19)	0.0610 (18)	0.0525 (17)	−0.0107 (16)	−0.0093 (16)	0.0013 (15)
C10	0.0645 (19)	0.0606 (19)	0.0618 (19)	−0.0026 (16)	−0.0074 (16)	−0.0061 (16)
C11	0.0631 (18)	0.0602 (18)	0.0536 (17)	0.0006 (15)	−0.0012 (15)	−0.0044 (15)

Geometric parameters (Å, º)

O1—C1	1.220 (3)	C4—C5	1.498 (4)
O2—N3	1.232 (4)	C4—H4A	0.97
O3—N3	1.238 (4)	C4—H4B	0.97
N1—C1	1.330 (4)	C5—H5A	0.97
N1—H1A	0.90	C5—H5B	0.97
N1—H1B	0.90	C6—C7	1.412 (4)
N2—C6	1.355 (3)	C6—C11	1.416 (4)
N2—C2	1.454 (3)	C7—C8	1.366 (4)
N2—C5	1.460 (4)	C7—H7A	0.93
N3—C9	1.443 (4)	C8—C9	1.378 (4)
C1—C2	1.527 (4)	C8—H8A	0.93
C2—C3	1.536 (4)	C9—C10	1.379 (4)
C2—H2A	0.98	C10—C11	1.367 (4)
C3—C4	1.491 (4)	C10—H10A	0.93
C3—H3A	0.97	C11—H11A	0.93
C3—H3B	0.97
C1—N1—H1A	124.5	C3—C4—H4B	110.4
C1—N1—H1B	126.5	C5—C4—H4B	110.4
H1A—N1—H1B	108.9	H4A—C4—H4B	108.6
C6—N2—C2	123.4 (2)	N2—C5—C4	104.1 (3)
C6—N2—C5	123.6 (3)	N2—C5—H5A	110.9
C2—N2—C5	113.0 (2)	C4—C5—H5A	110.9
O2—N3—O3	122.0 (3)	N2—C5—H5B	110.9
O2—N3—C9	119.2 (3)	C4—C5—H5B	110.9
O3—N3—C9	118.8 (3)	H5A—C5—H5B	109.0
O1—C1—N1	123.5 (3)	N2—C6—C7	121.3 (3)
O1—C1—C2	121.6 (3)	N2—C6—C11	121.0 (3)
N1—C1—C2	114.8 (3)	C7—C6—C11	117.7 (3)
N2—C2—C1	110.9 (2)	C8—C7—C6	121.1 (3)
N2—C2—C3	103.2 (2)	C8—C7—H7A	119.5
C1—C2—C3	110.9 (2)	C6—C7—H7A	119.5
N2—C2—H2A	110.5	C7—C8—C9	119.9 (3)
C1—C2—H2A	110.5	C7—C8—H8A	120.0
C3—C2—H2A	110.5	C9—C8—H8A	120.0
C4—C3—C2	104.9 (3)	C8—C9—C10	120.6 (3)
C4—C3—H3A	110.8	C8—C9—N3	119.7 (3)
C2—C3—H3A	110.8	C10—C9—N3	119.7 (3)
C4—C3—H3B	110.8	C11—C10—C9	120.6 (3)
C2—C3—H3B	110.8	C11—C10—H10A	119.7
H3A—C3—H3B	108.8	C9—C10—H10A	119.7
C3—C4—C5	106.8 (3)	C10—C11—C6	120.2 (3)
C3—C4—H4A	110.4	C10—C11—H11A	119.9
C5—C4—H4A	110.4	C6—C11—H11A	119.9
C6—N2—C2—C1	−71.2 (3)	C2—N2—C6—C11	−6.1 (4)
C5—N2—C2—C1	106.6 (3)	C5—N2—C6—C11	176.2 (3)
C6—N2—C2—C3	170.0 (3)	N2—C6—C7—C8	179.9 (3)
C5—N2—C2—C3	−12.1 (3)	C11—C6—C7—C8	0.9 (4)
O1—C1—C2—N2	−35.0 (4)	C6—C7—C8—C9	−0.2 (5)
N1—C1—C2—N2	147.8 (3)	C7—C8—C9—C10	−0.4 (5)
O1—C1—C2—C3	79.1 (4)	C7—C8—C9—N3	178.2 (3)
N1—C1—C2—C3	−98.2 (3)	O2—N3—C9—C8	−179.9 (3)
N2—C2—C3—C4	24.7 (3)	O3—N3—C9—C8	−0.1 (4)
C1—C2—C3—C4	−94.1 (3)	O2—N3—C9—C10	−1.3 (4)
C2—C3—C4—C5	−28.8 (4)	O3—N3—C9—C10	178.5 (3)
C6—N2—C5—C4	172.6 (3)	C8—C9—C10—C11	0.2 (4)
C2—N2—C5—C4	−5.2 (4)	N3—C9—C10—C11	−178.4 (3)
C3—C4—C5—N2	21.2 (4)	C9—C10—C11—C6	0.6 (4)
C2—N2—C6—C7	175.0 (3)	N2—C6—C11—C10	180.0 (3)
C5—N2—C6—C7	−2.7 (4)	C7—C6—C11—C10	−1.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1^i	0.90	2.17	2.959 (3)	146
N1—H1A···O2^ii	0.90	2.32	3.206 (3)	168

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) x, −y+3/2, z+1/2.