In the title compound, C
18H
19N
3O
3, the pyrrolidine ring has an envelope conformation. The crystal packing is stabilized by N—H
O and C—H
O hydrogen bonding.
Supporting information
CCDC reference: 628389
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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
top
Crystal data top
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) Å3 | Block, colourless |
Z = 4 | 0.22 × 0.20 × 0.12 mm |
F(000) = 688 | |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.046P)2 + 0.1349P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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+0.001xFc2λ3/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.86 | 2.16 | 3.010 (3) | 169 |
C12—H12···O2i | 0.98 | 2.49 | 3.292 (3) | 139 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |