(S)-Benzyl 2-(2-pyridylamino­carbon­yl)pyrrolidine-1-carboxyl­ate

In the title compound, C₁₈H₁₉N₃O₃, the pyrrolidine ring has an envelope conformation. The crystal packing is stabilized by N—H...O and C—H...O hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.039
• wR factor = 0.105
• Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are meaningless.
           From the CIF: _refine_ls_abs_structure_Flack    0.000
           From the CIF: _refine_ls_abs_structure_Flack_su   10.000
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ...      10.00
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..      10.00

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           26.40
           From the CIF: _reflns_number_total               1976
           Count of symmetry unique reflns         1990
           Completeness (_total/calc)             99.30%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12    = .          S

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Benzyl 2-(2-pyridylaminocarbonyl)pyrrolidine-1-carboxylate

Crystal data

C18H19N3O3	Dx = 1.278 Mg m^−3
Mr = 325.36	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2278 reflections
a = 8.9479 (18) Å	θ = 2.6–21.0°
b = 11.096 (2) Å	µ = 0.09 mm^−1
c = 17.035 (4) Å	T = 294 K
V = 1691.4 (6) Å^3	Block, colourless
Z = 4	0.22 × 0.20 × 0.12 mm
F(000) = 688

Data collection

Bruker SMART CCD area-detector diffractometer	1976 independent reflections
Radiation source: fine-focus sealed tube	1295 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
φ and ω scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (reference?)	h = −8→11
Tmin = 0.981, Tmax = 0.989	k = −12→13
9541 measured reflections	l = −21→21

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.046P)^2 + 0.1349P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.105	(Δ/σ)max = 0.006
S = 1.09	Δρmax = 0.15 e Å^−3
1976 reflections	Δρmin = −0.15 e Å^−3
218 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
7 restraints	Extinction coefficient: 0.018 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), ? Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0 (10)

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	0.6548 (2)	0.63599 (17)	0.28933 (12)	0.0553 (6)
O2	0.5472 (2)	0.8086 (2)	0.33126 (13)	0.0664 (7)
O3	0.6655 (3)	0.70088 (19)	0.10334 (15)	0.0726 (7)
N1	0.4565 (3)	0.7051 (2)	0.22646 (17)	0.0594 (7)
N2	0.6652 (3)	0.4961 (2)	0.10671 (13)	0.0494 (6)
H2	0.6132	0.4356	0.1224	0.059*
N3	0.8247 (4)	0.3509 (3)	0.06268 (16)	0.0670 (8)
C1	0.9662 (4)	0.5074 (3)	0.39414 (17)	0.0603 (9)
H1	0.9361	0.5230	0.4454	0.072*
C2	1.0845 (4)	0.4289 (3)	0.3807 (2)	0.0699 (10)
H2A	1.1348	0.3943	0.4228	0.084*
C3	1.1269 (4)	0.4025 (4)	0.3058 (2)	0.0795 (11)
H3	1.2064	0.3505	0.2965	0.095*
C4	1.0508 (4)	0.4536 (4)	0.2441 (2)	0.0783 (11)
H4	1.0766	0.4334	0.1928	0.094*
C5	0.9367 (3)	0.5345 (3)	0.25738 (17)	0.0607 (9)
H5	0.8888	0.5706	0.2150	0.073*
C6	0.8930 (3)	0.5625 (3)	0.33277 (16)	0.0478 (7)
C7	0.7698 (4)	0.6511 (3)	0.34808 (18)	0.0589 (9)
H7A	0.7282	0.6376	0.3999	0.071*
H7B	0.8089	0.7325	0.3460	0.071*
C8	0.5503 (4)	0.7240 (3)	0.28553 (19)	0.0523 (8)
C9	0.3339 (4)	0.7886 (4)	0.2102 (3)	0.0845 (12)
H9A	0.3717	0.8649	0.1909	0.101*
H9B	0.2751	0.8031	0.2571	0.101*
C10	0.2445 (5)	0.7277 (4)	0.1502 (3)	0.1174 (18)
H10A	0.2169	0.7845	0.1094	0.141*
H10B	0.1536	0.6961	0.1735	0.141*
C11	0.3335 (4)	0.6274 (4)	0.1157 (3)	0.0988 (15)
H11A	0.3694	0.6494	0.0639	0.119*
H11B	0.2727	0.5554	0.1110	0.119*
C12	0.4657 (3)	0.6050 (3)	0.17160 (19)	0.0581 (8)
H12	0.4538	0.5280	0.1991	0.070*
C13	0.6106 (3)	0.6067 (3)	0.12470 (18)	0.0504 (7)
C14	0.7965 (3)	0.4690 (3)	0.06555 (16)	0.0500 (8)
C15	0.8883 (4)	0.5536 (4)	0.0312 (2)	0.0675 (9)
H15	0.8654	0.6352	0.0342	0.081*
C16	1.0146 (4)	0.5150 (5)	−0.0076 (2)	0.0867 (13)
H16	1.0780	0.5705	−0.0314	0.104*
C17	1.0459 (5)	0.3947 (5)	−0.0109 (2)	0.0889 (13)
H17	1.1310	0.3665	−0.0363	0.107*
C18	0.9487 (5)	0.3175 (4)	0.0242 (2)	0.0859 (13)
H18	0.9697	0.2355	0.0212	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0531 (13)	0.0504 (12)	0.0623 (12)	0.0142 (10)	−0.0041 (11)	−0.0079 (10)
O2	0.0743 (15)	0.0558 (14)	0.0692 (14)	0.0212 (13)	0.0049 (13)	−0.0126 (12)
O3	0.0721 (15)	0.0426 (13)	0.1030 (19)	−0.0074 (12)	0.0169 (15)	−0.0029 (13)
N1	0.0512 (15)	0.0576 (17)	0.0693 (17)	0.0189 (14)	−0.0043 (15)	−0.0091 (14)
N2	0.0539 (15)	0.0373 (13)	0.0571 (14)	−0.0023 (11)	0.0059 (13)	−0.0009 (11)
N3	0.078 (2)	0.0573 (17)	0.0653 (17)	0.0187 (15)	−0.0102 (16)	−0.0051 (14)
C1	0.070 (2)	0.065 (2)	0.0458 (16)	0.0057 (19)	−0.0030 (17)	−0.0021 (16)
C2	0.064 (2)	0.072 (2)	0.074 (2)	0.0201 (19)	−0.0136 (19)	0.006 (2)
C3	0.060 (2)	0.090 (3)	0.089 (3)	0.027 (2)	0.005 (2)	−0.009 (2)
C4	0.068 (2)	0.105 (3)	0.062 (2)	0.028 (2)	0.0100 (19)	−0.010 (2)
C5	0.0557 (19)	0.077 (2)	0.0496 (17)	0.0141 (18)	0.0029 (15)	−0.0018 (17)
C6	0.0446 (16)	0.0468 (17)	0.0519 (17)	0.0017 (13)	0.0002 (14)	−0.0024 (14)
C7	0.062 (2)	0.065 (2)	0.0494 (17)	0.0140 (17)	−0.0058 (16)	−0.0042 (16)
C8	0.0525 (18)	0.0435 (17)	0.0610 (19)	0.0100 (16)	0.0097 (18)	0.0018 (16)
C9	0.066 (2)	0.082 (3)	0.105 (3)	0.031 (2)	−0.016 (2)	−0.007 (3)
C10	0.095 (3)	0.102 (3)	0.155 (4)	0.029 (3)	−0.042 (3)	−0.007 (3)
C11	0.047 (2)	0.141 (4)	0.108 (3)	0.011 (2)	−0.016 (2)	−0.036 (3)
C12	0.0454 (17)	0.0556 (19)	0.073 (2)	0.0014 (16)	−0.0010 (17)	−0.0064 (18)
C13	0.0480 (17)	0.0447 (18)	0.0583 (18)	−0.0021 (15)	−0.0028 (15)	−0.0054 (15)
C14	0.0530 (18)	0.0521 (19)	0.0450 (16)	0.0030 (15)	−0.0099 (15)	−0.0044 (15)
C15	0.056 (2)	0.071 (2)	0.075 (2)	−0.0042 (19)	0.0088 (18)	−0.002 (2)
C16	0.054 (2)	0.123 (4)	0.083 (3)	−0.004 (2)	0.008 (2)	−0.018 (3)
C17	0.055 (2)	0.126 (4)	0.085 (3)	0.028 (3)	−0.011 (2)	−0.030 (3)
C18	0.090 (3)	0.084 (3)	0.083 (3)	0.041 (3)	−0.015 (3)	−0.018 (2)

Geometric parameters (Å, º)

O1—C8	1.354 (3)	C6—C7	1.500 (4)
O1—C7	1.445 (4)	C7—H7A	0.9700
O2—C8	1.220 (3)	C7—H7B	0.9700
O3—C13	1.211 (4)	C9—C10	1.463 (6)
N1—C8	1.327 (4)	C9—H9A	0.9700
N1—C12	1.454 (4)	C9—H9B	0.9700
N1—C9	1.463 (4)	C10—C11	1.489 (5)
N2—C13	1.356 (4)	C10—H10A	0.9700
N2—C14	1.401 (3)	C10—H10B	0.9700
N2—H2	0.8600	C11—C12	1.539 (5)
N3—C14	1.336 (4)	C11—H11A	0.9700
N3—C18	1.341 (5)	C11—H11B	0.9700
C1—C6	1.377 (4)	C12—C13	1.523 (4)
C1—C2	1.390 (4)	C12—H12	0.9800
C1—H1	0.9300	C14—C15	1.377 (4)
C2—C3	1.363 (5)	C15—C16	1.378 (5)
C2—H2A	0.9300	C15—H15	0.9300
C3—C4	1.374 (5)	C16—C17	1.364 (6)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.378 (4)	C17—C18	1.359 (6)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.378 (4)	C18—H18	0.9300
C5—H5	0.9300
C8—O1—C7	116.2 (2)	C10—C9—H9B	110.9
C8—N1—C12	125.0 (2)	H9A—C9—H9B	108.9
C8—N1—C9	121.2 (3)	C9—C10—C11	109.2 (3)
C12—N1—C9	113.9 (3)	C9—C10—H10A	109.8
C13—N2—C14	127.6 (3)	C11—C10—H10A	109.8
C13—N2—H2	116.2	C9—C10—H10B	109.8
C14—N2—H2	116.2	C11—C10—H10B	109.8
C14—N3—C18	116.4 (3)	H10A—C10—H10B	108.3
C6—C1—C2	121.0 (3)	C10—C11—C12	106.7 (3)
C6—C1—H1	119.5	C10—C11—H11A	110.4
C2—C1—H1	119.5	C12—C11—H11A	110.4
C3—C2—C1	120.0 (3)	C10—C11—H11B	110.4
C3—C2—H2A	120.0	C12—C11—H11B	110.4
C1—C2—H2A	120.0	H11A—C11—H11B	108.6
C2—C3—C4	119.4 (3)	N1—C12—C13	112.1 (3)
C2—C3—H3	120.3	N1—C12—C11	103.4 (3)
C4—C3—H3	120.3	C13—C12—C11	109.1 (3)
C3—C4—C5	120.6 (3)	N1—C12—H12	110.7
C3—C4—H4	119.7	C13—C12—H12	110.7
C5—C4—H4	119.7	C11—C12—H12	110.7
C4—C5—C6	120.7 (3)	O3—C13—N2	124.5 (3)
C4—C5—H5	119.7	O3—C13—C12	120.9 (3)
C6—C5—H5	119.7	N2—C13—C12	114.5 (3)
C1—C6—C5	118.2 (3)	N3—C14—C15	122.7 (3)
C1—C6—C7	120.6 (3)	N3—C14—N2	112.8 (3)
C5—C6—C7	121.2 (3)	C15—C14—N2	124.5 (3)
O1—C7—C6	109.1 (2)	C14—C15—C16	118.8 (4)
O1—C7—H7A	109.9	C14—C15—H15	120.6
C6—C7—H7A	109.9	C16—C15—H15	120.6
O1—C7—H7B	109.9	C17—C16—C15	119.4 (4)
C6—C7—H7B	109.9	C17—C16—H16	120.3
H7A—C7—H7B	108.3	C15—C16—H16	120.3
O2—C8—N1	126.3 (3)	C18—C17—C16	117.9 (4)
O2—C8—O1	122.7 (3)	C18—C17—H17	121.1
N1—C8—O1	111.0 (3)	C16—C17—H17	121.1
N1—C9—C10	104.5 (3)	N3—C18—C17	124.8 (4)
N1—C9—H9A	110.9	N3—C18—H18	117.6
C10—C9—H9A	110.9	C17—C18—H18	117.6
N1—C9—H9B	110.9
C6—C1—C2—C3	−1.9 (5)	C9—N1—C12—C13	116.6 (3)
C1—C2—C3—C4	−0.5 (6)	C8—N1—C12—C11	−179.3 (3)
C2—C3—C4—C5	2.6 (6)	C9—N1—C12—C11	−0.8 (4)
C3—C4—C5—C6	−2.4 (6)	C10—C11—C12—N1	−8.7 (4)
C2—C1—C6—C5	2.2 (5)	C10—C11—C12—C13	−128.1 (4)
C2—C1—C6—C7	−177.4 (3)	C14—N2—C13—O3	4.2 (5)
C4—C5—C6—C1	0.0 (5)	C14—N2—C13—C12	−178.9 (2)
C4—C5—C6—C7	179.5 (3)	N1—C12—C13—O3	−36.8 (4)
C8—O1—C7—C6	−167.5 (2)	C11—C12—C13—O3	77.0 (4)
C1—C6—C7—O1	−142.7 (3)	N1—C12—C13—N2	146.2 (3)
C5—C6—C7—O1	37.8 (4)	C11—C12—C13—N2	−99.9 (3)
C12—N1—C8—O2	178.2 (3)	C18—N3—C14—C15	0.0 (5)
C9—N1—C8—O2	−0.2 (5)	C18—N3—C14—N2	180.0 (3)
C12—N1—C8—O1	−1.3 (4)	C13—N2—C14—N3	175.3 (3)
C9—N1—C8—O1	−179.8 (3)	C13—N2—C14—C15	−4.8 (4)
C7—O1—C8—O2	−3.7 (4)	N3—C14—C15—C16	−0.1 (5)
C7—O1—C8—N1	175.9 (2)	N2—C14—C15—C16	180.0 (3)
C8—N1—C9—C10	−171.4 (3)	C14—C15—C16—C17	−0.2 (5)
C12—N1—C9—C10	10.0 (5)	C15—C16—C17—C18	0.6 (6)
N1—C9—C10—C11	−15.4 (5)	C14—N3—C18—C17	0.5 (5)
C9—C10—C11—C12	15.3 (6)	C16—C17—C18—N3	−0.8 (6)
C8—N1—C12—C13	−61.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2^i	0.86	2.16	3.010 (3)	169
C12—H12···O2^i	0.98	2.49	3.292 (3)	139

Symmetry code: (i) −x+1, y−1/2, −z+1/2.