In the title compound (systematic name: (
S)-4-{3-[2-(dimethylamino)ethyl]-1
H-indol-5-ylmethyl}oxazolidin-2-one chloroform solvate), C
16H
21N
3O
2·CHCl
3, the oxazolidinone ring is in a twist conformation. Intermolecular N—H
O, N—H
N and C—H
O hydrogen bonds stabilize the crystal packing.
Supporting information
CCDC reference: 642935
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.079
- wR factor = 0.243
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C17
PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.20
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 25.00
From the CIF: _reflns_number_total 3647
Count of symmetry unique reflns 2104
Completeness (_total/calc) 173.34%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1543
Fraction of Friedel pairs measured 0.733
Are heavy atom types Z>Si present yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
1 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
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97.
(
S)-4-[3-{2-(dimethylamino)ethyl}-1
H-indol-5-yl
methyl]-2-oxazolidinone. chloroform solvate
top
Crystal data top
C16H21N3O2·CHCl3 | F(000) = 848 |
Mr = 406.73 | Dx = 1.301 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4346 reflections |
a = 7.9987 (6) Å | θ = 2.6–21.6° |
b = 12.8279 (9) Å | µ = 0.46 mm−1 |
c = 20.2396 (14) Å | T = 294 K |
V = 2076.7 (3) Å3 | Block, colorless |
Z = 4 | 0.20 × 0.16 × 0.08 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2981 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
ω scan | h = −9→9 |
15108 measured reflections | k = −15→15 |
3647 independent reflections | l = −24→23 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.079 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.243 | w = 1/[σ2(Fo2) + (0.1384P)2 + 1.1361P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3647 reflections | Δρmax = 0.49 e Å−3 |
238 parameters | Δρmin = −0.32 e Å−3 |
7 restraints | Absolute structure: Flack (1983), 1543 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.0 (2) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.3984 (7) | 0.5515 (4) | 1.0805 (3) | 0.0861 (15) | |
H1 | 0.3169 | 0.5935 | 1.0996 | 0.103* | |
C2 | 0.3939 (7) | 0.5133 (4) | 1.0148 (2) | 0.0792 (14) | |
C3 | 0.5361 (5) | 0.4507 (3) | 1.0091 (2) | 0.0591 (10) | |
C4 | 0.5978 (6) | 0.3903 (3) | 0.9588 (2) | 0.0610 (10) | |
H4 | 0.5405 | 0.3873 | 0.9188 | 0.073* | |
C5 | 0.7427 (5) | 0.3344 (3) | 0.96635 (19) | 0.0568 (9) | |
C6 | 0.8302 (6) | 0.3419 (4) | 1.0260 (2) | 0.0640 (11) | |
H6 | 0.9295 | 0.3049 | 1.0307 | 0.077* | |
C7 | 0.7750 (5) | 0.4018 (3) | 1.0776 (2) | 0.0614 (10) | |
H7 | 0.8355 | 0.4060 | 1.1167 | 0.074* | |
C8 | 0.6276 (5) | 0.4554 (3) | 1.06984 (18) | 0.0557 (9) | |
C9 | 0.2709 (7) | 0.5314 (5) | 0.9565 (3) | 0.0768 (17) | 0.788 (9) |
H9A | 0.3279 | 0.5701 | 0.9221 | 0.092* | 0.788 (9) |
H9B | 0.2389 | 0.4644 | 0.9382 | 0.092* | 0.788 (9) |
C91 | 0.2080 (14) | 0.4940 (11) | 1.0026 (11) | 0.0768 (17) | 0.212 (9) |
H91A | 0.1959 | 0.4372 | 0.9713 | 0.092* | 0.212 (9) |
H91B | 0.1560 | 0.4726 | 1.0437 | 0.092* | 0.212 (9) |
C10 | 0.1170 (7) | 0.5892 (4) | 0.9761 (3) | 0.0840 (15) | |
H10A | 0.0649 | 0.5544 | 1.0133 | 0.101* | |
H10B | 0.1471 | 0.6592 | 0.9899 | 0.101* | |
C11 | −0.1537 (9) | 0.6349 (4) | 0.9505 (3) | 0.0995 (18) | |
H11A | −0.1838 | 0.5946 | 0.9886 | 0.149* | |
H11B | −0.2409 | 0.6300 | 0.9180 | 0.149* | |
H11C | −0.1388 | 0.7065 | 0.9630 | 0.149* | |
C12 | 0.0528 (8) | 0.6619 (4) | 0.8672 (3) | 0.0909 (16) | |
H12A | 0.0871 | 0.7287 | 0.8838 | 0.136* | |
H12B | −0.0394 | 0.6708 | 0.8374 | 0.136* | |
H12C | 0.1444 | 0.6299 | 0.8443 | 0.136* | |
C13 | 0.8034 (7) | 0.2636 (4) | 0.9108 (2) | 0.0717 (12) | |
H13A | 0.8181 | 0.1939 | 0.9284 | 0.086* | |
H13B | 0.7169 | 0.2600 | 0.8773 | 0.086* | |
C14 | 0.9639 (6) | 0.2963 (3) | 0.8782 (2) | 0.0640 (11) | |
H14 | 1.0594 | 0.2884 | 0.9081 | 0.077* | |
C15 | 0.9901 (8) | 0.2356 (4) | 0.8140 (2) | 0.0846 (15) | |
H15A | 1.1073 | 0.2187 | 0.8079 | 0.102* | |
H15B | 0.9258 | 0.1715 | 0.8143 | 0.102* | |
C16 | 0.9264 (6) | 0.4031 (4) | 0.7873 (2) | 0.0705 (12) | |
N1 | 0.5383 (6) | 0.5179 (3) | 1.11128 (19) | 0.0717 (10) | |
H1N | 0.567 (5) | 0.529 (3) | 1.1492 (9) | 0.073 (11)* | |
N2 | 0.0011 (5) | 0.5949 (3) | 0.92286 (18) | 0.0697 (10) | |
N3 | 0.9543 (5) | 0.4019 (3) | 0.85169 (16) | 0.0617 (8) | |
H3N | 0.949 (6) | 0.454 (2) | 0.8752 (18) | 0.060 (12)* | |
O1 | 0.9330 (5) | 0.3038 (3) | 0.76345 (15) | 0.0838 (11) | |
O2 | 0.8979 (6) | 0.4770 (3) | 0.75148 (17) | 0.0976 (13) | |
C17 | 0.5301 (11) | 0.3035 (9) | 0.7183 (4) | 0.148 (3) | |
H17 | 0.6448 | 0.3122 | 0.7344 | 0.178* | |
Cl1 | 0.5289 (3) | 0.3263 (3) | 0.63734 (12) | 0.1840 (14) | |
Cl2 | 0.4026 (7) | 0.3871 (3) | 0.7619 (2) | 0.253 (2) | |
Cl3 | 0.4669 (7) | 0.1785 (3) | 0.7358 (2) | 0.246 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.071 (3) | 0.076 (3) | 0.111 (4) | 0.009 (2) | 0.006 (3) | −0.022 (3) |
C2 | 0.079 (3) | 0.064 (3) | 0.095 (4) | 0.009 (2) | −0.017 (3) | −0.016 (3) |
C3 | 0.056 (2) | 0.054 (2) | 0.067 (2) | −0.0043 (19) | −0.0088 (19) | −0.0011 (18) |
C4 | 0.071 (3) | 0.062 (2) | 0.051 (2) | −0.004 (2) | −0.0110 (19) | −0.0029 (18) |
C5 | 0.069 (2) | 0.0512 (19) | 0.050 (2) | −0.0071 (19) | 0.0064 (19) | 0.0025 (16) |
C6 | 0.060 (2) | 0.071 (3) | 0.061 (2) | 0.004 (2) | 0.001 (2) | 0.012 (2) |
C7 | 0.067 (2) | 0.072 (2) | 0.0458 (19) | 0.002 (2) | −0.0058 (18) | 0.0068 (19) |
C8 | 0.066 (2) | 0.056 (2) | 0.0450 (19) | −0.0049 (18) | 0.0016 (18) | 0.0043 (17) |
C9 | 0.078 (4) | 0.095 (4) | 0.058 (3) | 0.008 (3) | 0.000 (3) | −0.013 (3) |
C91 | 0.078 (4) | 0.095 (4) | 0.058 (3) | 0.008 (3) | 0.000 (3) | −0.013 (3) |
C10 | 0.104 (4) | 0.064 (3) | 0.085 (3) | 0.002 (3) | −0.021 (3) | 0.001 (2) |
C11 | 0.125 (5) | 0.081 (3) | 0.093 (4) | −0.002 (3) | 0.023 (4) | 0.009 (3) |
C12 | 0.095 (4) | 0.089 (3) | 0.089 (4) | −0.005 (3) | −0.004 (3) | 0.035 (3) |
C13 | 0.094 (3) | 0.057 (2) | 0.064 (3) | −0.002 (2) | 0.004 (2) | −0.007 (2) |
C14 | 0.074 (3) | 0.064 (2) | 0.053 (2) | 0.013 (2) | −0.001 (2) | −0.0066 (19) |
C15 | 0.108 (4) | 0.074 (3) | 0.072 (3) | 0.017 (3) | 0.016 (3) | −0.014 (2) |
C16 | 0.085 (3) | 0.079 (3) | 0.048 (2) | 0.012 (3) | −0.005 (2) | −0.004 (2) |
N1 | 0.083 (3) | 0.074 (2) | 0.059 (2) | 0.005 (2) | 0.003 (2) | −0.0084 (19) |
N2 | 0.091 (3) | 0.0535 (18) | 0.064 (2) | −0.0089 (18) | −0.020 (2) | 0.0121 (17) |
N3 | 0.082 (2) | 0.0606 (19) | 0.0428 (16) | 0.0002 (18) | 0.0002 (17) | −0.0039 (16) |
O1 | 0.109 (3) | 0.091 (2) | 0.0511 (16) | 0.019 (2) | −0.0079 (17) | −0.0216 (16) |
O2 | 0.144 (4) | 0.093 (2) | 0.0554 (18) | 0.017 (2) | −0.016 (2) | 0.0075 (18) |
C17 | 0.099 (5) | 0.224 (10) | 0.121 (6) | −0.022 (6) | −0.026 (5) | 0.015 (7) |
Cl1 | 0.1426 (18) | 0.284 (4) | 0.1259 (17) | 0.045 (2) | 0.0032 (14) | 0.081 (2) |
Cl2 | 0.291 (5) | 0.237 (4) | 0.231 (4) | −0.051 (4) | 0.039 (4) | −0.089 (4) |
Cl3 | 0.280 (5) | 0.210 (3) | 0.249 (4) | 0.024 (3) | 0.101 (4) | 0.092 (3) |
Geometric parameters (Å, º) top
C1—N1 | 1.352 (7) | C11—N2 | 1.452 (8) |
C1—C2 | 1.417 (6) | C11—H11A | 0.9600 |
C1—H1 | 0.9300 | C11—H11B | 0.9600 |
C2—C3 | 1.397 (7) | C11—H11C | 0.9600 |
C2—C91 | 1.528 (10) | C12—N2 | 1.476 (6) |
C2—C9 | 1.554 (6) | C12—H12A | 0.9600 |
C3—C4 | 1.372 (6) | C12—H12B | 0.9600 |
C3—C8 | 1.432 (6) | C12—H12C | 0.9600 |
C4—C5 | 1.371 (6) | C13—C14 | 1.503 (7) |
C4—H4 | 0.9300 | C13—H13A | 0.9700 |
C5—C6 | 1.398 (6) | C13—H13B | 0.9700 |
C5—C13 | 1.526 (6) | C14—N3 | 1.459 (6) |
C6—C7 | 1.370 (6) | C14—C15 | 1.529 (6) |
C6—H6 | 0.9300 | C14—H14 | 0.9800 |
C7—C8 | 1.374 (6) | C15—O1 | 1.422 (6) |
C7—H7 | 0.9300 | C15—H15A | 0.9700 |
C8—N1 | 1.362 (5) | C15—H15B | 0.9700 |
C9—C10 | 1.491 (7) | C16—O2 | 1.216 (6) |
C9—H9A | 0.9700 | C16—N3 | 1.322 (6) |
C9—H9B | 0.9700 | C16—O1 | 1.363 (6) |
C91—C10 | 1.520 (10) | N1—H1N | 0.82 (3) |
C91—H91A | 0.9700 | N3—H3N | 0.82 (3) |
C91—H91B | 0.9700 | C17—Cl1 | 1.664 (9) |
C10—N2 | 1.423 (6) | C17—Cl3 | 1.718 (11) |
C10—H10A | 0.9700 | C17—Cl2 | 1.723 (11) |
C10—H10B | 0.9700 | C17—H17 | 0.9800 |
| | | |
N1—C1—C2 | 110.1 (4) | N2—C11—H11B | 109.5 |
N1—C1—H1 | 125.0 | H11A—C11—H11B | 109.5 |
C2—C1—H1 | 125.0 | N2—C11—H11C | 109.5 |
C3—C2—C1 | 104.8 (4) | H11A—C11—H11C | 109.5 |
C3—C2—C91 | 133.3 (7) | H11B—C11—H11C | 109.5 |
C1—C2—C91 | 103.4 (10) | N2—C12—H12A | 109.5 |
C3—C2—C9 | 122.6 (4) | N2—C12—H12B | 109.5 |
C1—C2—C9 | 132.6 (5) | H12A—C12—H12B | 109.5 |
C4—C3—C2 | 132.7 (4) | N2—C12—H12C | 109.5 |
C4—C3—C8 | 118.5 (4) | H12A—C12—H12C | 109.5 |
C2—C3—C8 | 108.8 (4) | H12B—C12—H12C | 109.5 |
C5—C4—C3 | 121.1 (4) | C14—C13—C5 | 115.4 (4) |
C5—C4—H4 | 119.5 | C14—C13—H13A | 108.4 |
C3—C4—H4 | 119.5 | C5—C13—H13A | 108.4 |
C4—C5—C6 | 119.0 (4) | C14—C13—H13B | 108.4 |
C4—C5—C13 | 119.9 (4) | C5—C13—H13B | 108.4 |
C6—C5—C13 | 121.1 (4) | H13A—C13—H13B | 107.5 |
C7—C6—C5 | 122.3 (4) | N3—C14—C13 | 112.1 (4) |
C7—C6—H6 | 118.8 | N3—C14—C15 | 99.7 (3) |
C5—C6—H6 | 118.8 | C13—C14—C15 | 110.3 (4) |
C6—C7—C8 | 118.1 (4) | N3—C14—H14 | 111.4 |
C6—C7—H7 | 121.0 | C13—C14—H14 | 111.4 |
C8—C7—H7 | 121.0 | C15—C14—H14 | 111.4 |
N1—C8—C7 | 132.4 (4) | O1—C15—C14 | 104.7 (4) |
N1—C8—C3 | 106.6 (4) | O1—C15—H15A | 110.8 |
C7—C8—C3 | 121.0 (4) | C14—C15—H15A | 110.8 |
C10—C9—C2 | 113.3 (4) | O1—C15—H15B | 110.8 |
C10—C9—H9A | 108.9 | C14—C15—H15B | 110.8 |
C2—C9—H9A | 108.9 | H15A—C15—H15B | 108.9 |
C10—C9—H9B | 108.9 | O2—C16—N3 | 128.9 (4) |
C2—C9—H9B | 108.9 | O2—C16—O1 | 121.7 (4) |
H9A—C9—H9B | 107.7 | N3—C16—O1 | 109.4 (4) |
C10—C91—C2 | 113.1 (9) | C1—N1—C8 | 109.7 (4) |
C10—C91—H91A | 109.0 | C1—N1—H1N | 128 (3) |
C2—C91—H91A | 109.0 | C8—N1—H1N | 122 (3) |
C10—C91—H91B | 109.0 | C10—N2—C11 | 106.4 (4) |
C2—C91—H91B | 109.0 | C10—N2—C12 | 115.1 (4) |
H91A—C91—H91B | 107.8 | C11—N2—C12 | 109.1 (4) |
N2—C10—C9 | 111.2 (4) | C16—N3—C14 | 112.4 (4) |
N2—C10—C91 | 128.4 (8) | C16—N3—H3N | 124 (3) |
C9—C10—C91 | 45.4 (8) | C14—N3—H3N | 123 (3) |
N2—C10—H10A | 109.4 | C16—O1—C15 | 109.4 (3) |
C9—C10—H10A | 109.4 | Cl1—C17—Cl3 | 111.5 (6) |
C91—C10—H10A | 64.0 | Cl1—C17—Cl2 | 113.1 (6) |
N2—C10—H10B | 109.4 | Cl3—C17—Cl2 | 107.5 (5) |
C9—C10—H10B | 109.4 | Cl1—C17—H17 | 108.2 |
C91—C10—H10B | 121.5 | Cl3—C17—H17 | 108.2 |
H10A—C10—H10B | 108.0 | Cl2—C17—H17 | 108.2 |
N2—C11—H11A | 109.5 | | |
| | | |
N1—C1—C2—C3 | 2.7 (6) | C1—C2—C91—C10 | 88.3 (14) |
N1—C1—C2—C91 | 145.1 (6) | C9—C2—C91—C10 | −50.3 (9) |
N1—C1—C2—C9 | −176.1 (6) | C2—C9—C10—N2 | −174.2 (5) |
C1—C2—C3—C4 | 177.6 (5) | C2—C9—C10—C91 | −50.8 (9) |
C91—C2—C3—C4 | 52.3 (13) | C2—C91—C10—N2 | 134.4 (10) |
C9—C2—C3—C4 | −3.5 (9) | C2—C91—C10—C9 | 51.9 (9) |
C1—C2—C3—C8 | −2.5 (5) | C4—C5—C13—C14 | 113.5 (5) |
C91—C2—C3—C8 | −127.8 (11) | C6—C5—C13—C14 | −68.0 (5) |
C9—C2—C3—C8 | 176.4 (5) | C5—C13—C14—N3 | −56.6 (5) |
C2—C3—C4—C5 | −179.3 (5) | C5—C13—C14—C15 | −166.7 (4) |
C8—C3—C4—C5 | 0.8 (6) | N3—C14—C15—O1 | −20.1 (5) |
C3—C4—C5—C6 | −1.7 (6) | C13—C14—C15—O1 | 97.9 (5) |
C3—C4—C5—C13 | 176.8 (4) | C2—C1—N1—C8 | −1.8 (6) |
C4—C5—C6—C7 | 1.1 (6) | C7—C8—N1—C1 | −179.0 (5) |
C13—C5—C6—C7 | −177.4 (4) | C3—C8—N1—C1 | 0.2 (5) |
C5—C6—C7—C8 | 0.4 (6) | C9—C10—N2—C11 | 169.7 (5) |
C6—C7—C8—N1 | 177.9 (4) | C91—C10—N2—C11 | 120.4 (10) |
C6—C7—C8—C3 | −1.3 (6) | C9—C10—N2—C12 | −69.3 (6) |
C4—C3—C8—N1 | −178.6 (4) | C91—C10—N2—C12 | −118.6 (10) |
C2—C3—C8—N1 | 1.5 (5) | O2—C16—N3—C14 | 173.2 (5) |
C4—C3—C8—C7 | 0.7 (6) | O1—C16—N3—C14 | −6.5 (6) |
C2—C3—C8—C7 | −179.2 (4) | C13—C14—N3—C16 | −100.0 (5) |
C3—C2—C9—C10 | 172.5 (5) | C15—C14—N3—C16 | 16.7 (5) |
C1—C2—C9—C10 | −9.0 (10) | O2—C16—O1—C15 | 172.2 (5) |
C91—C2—C9—C10 | 51.8 (10) | N3—C16—O1—C15 | −8.0 (6) |
C3—C2—C91—C10 | −145.8 (9) | C14—C15—O1—C16 | 18.2 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.82 (3) | 2.09 (2) | 2.884 (5) | 165 (4) |
N3—H3N···N2ii | 0.82 (3) | 2.10 (2) | 2.889 (5) | 164 (4) |
C17—H17···O1 | 0.98 | 2.38 | 3.350 (9) | 170 |
Symmetry codes: (i) −x+3/2, −y+1, z+1/2; (ii) x+1, y, z. |