Sumatriptan, {3-[2-(dimethylamino)ethyl]-1
H-indol-5-yl}-
N-methylmethanesulfonamide, C
14H
21N
3O
2S, is reported in its parent form. The molecular geometry is similar to that of sumatriptan succinate, but the two differ in their side-chain orientations. Intermolecular N—H
O and N—H
N hydrogen bonds form a glide-symmetric chain along the
c axis.
Supporting information
CCDC reference: 601136
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.127
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.09
PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C10 .. 5.13 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1
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
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
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: SHELXTL/PC (Sheldrick, 1990), QMOL (Gans & Shalloway, 2001)
and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.
{3-[2-(dimethylamino)ethyl]-1
H-indol-5-yl}-
N-methylmethanesulfonamide
top
Crystal data top
C14H21N3O2S | F(000) = 632 |
Mr = 295.40 | Dx = 1.276 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7659 reflections |
a = 6.3216 (3) Å | θ = 2.1–27.9° |
b = 10.1290 (5) Å | µ = 0.22 mm−1 |
c = 24.1541 (12) Å | T = 273 K |
β = 96.318 (1)° | Needle, yellow |
V = 1537.23 (13) Å3 | 0.22 × 0.11 × 0.08 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2494 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
ω scans | h = −7→7 |
14386 measured reflections | k = −12→12 |
2709 independent reflections | l = −28→28 |
Refinement top
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0686P)2 + 0.667P] where P = (Fo2 + 2Fc2)/3 |
2709 reflections | (Δ/σ)max = 0.001 |
192 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
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 | |
S1 | −0.28124 (8) | 1.04034 (5) | 0.13908 (2) | 0.0510 (2) | |
O1 | −0.2090 (3) | 0.91058 (17) | 0.15409 (7) | 0.0737 (5) | |
O2 | −0.1550 (3) | 1.12094 (19) | 0.10749 (7) | 0.0724 (5) | |
N1 | 0.1766 (3) | 0.73779 (18) | 0.46980 (7) | 0.0591 (5) | |
N2 | 0.4624 (3) | 1.16874 (19) | 0.33896 (8) | 0.0610 (5) | |
H2N | 0.557 (4) | 1.221 (3) | 0.3423 (10) | 0.061 (7)* | |
N3 | −0.5103 (3) | 1.02963 (19) | 0.10463 (8) | 0.0549 (5) | |
H3N | −0.545 (4) | 1.098 (3) | 0.0856 (10) | 0.060 (7)* | |
C1 | 0.1452 (3) | 1.07415 (19) | 0.31524 (8) | 0.0477 (5) | |
C2 | −0.0497 (3) | 1.0584 (2) | 0.28283 (8) | 0.0506 (5) | |
H2 | −0.1430 | 0.9922 | 0.2912 | 0.061* | |
C3 | −0.1029 (3) | 1.1415 (2) | 0.23849 (8) | 0.0531 (5) | |
C4 | 0.0374 (4) | 1.2421 (2) | 0.22654 (9) | 0.0610 (6) | |
H4 | −0.0019 | 1.2985 | 0.1968 | 0.073* | |
C5 | 0.2309 (4) | 1.2598 (2) | 0.25731 (9) | 0.0597 (6) | |
H5 | 0.3228 | 1.3267 | 0.2488 | 0.072* | |
C6 | 0.2846 (3) | 1.17445 (19) | 0.30164 (8) | 0.0503 (5) | |
C7 | 0.4381 (4) | 1.0695 (2) | 0.37603 (10) | 0.0633 (6) | |
H7 | 0.5383 | 1.0468 | 0.4056 | 0.076* | |
C8 | 0.2470 (4) | 1.0086 (2) | 0.36368 (9) | 0.0566 (5) | |
C9 | 0.1506 (4) | 0.8961 (3) | 0.39287 (10) | 0.0751 (7) | |
H9A | 0.0122 | 0.9237 | 0.4024 | 0.090* | |
H9B | 0.1280 | 0.8229 | 0.3670 | 0.090* | |
C10 | 0.2771 (4) | 0.8482 (2) | 0.44404 (9) | 0.0645 (6) | |
H10A | 0.4164 | 0.8209 | 0.4350 | 0.077* | |
H10B | 0.2974 | 0.9202 | 0.4706 | 0.077* | |
C11 | 0.0053 (5) | 0.7766 (3) | 0.50167 (12) | 0.0869 (8) | |
H11A | 0.0588 | 0.8371 | 0.5304 | 0.130* | |
H11B | −0.0509 | 0.6998 | 0.5182 | 0.130* | |
H11C | −0.1053 | 0.8185 | 0.4775 | 0.130* | |
C12 | 0.3391 (5) | 0.6643 (3) | 0.50525 (11) | 0.0807 (8) | |
H12A | 0.4000 | 0.7202 | 0.5349 | 0.121* | |
H12B | 0.4487 | 0.6357 | 0.4834 | 0.121* | |
H12C | 0.2751 | 0.5887 | 0.5207 | 0.121* | |
C13 | −0.3111 (4) | 1.1250 (2) | 0.20261 (9) | 0.0614 (6) | |
H13A | −0.3727 | 1.2113 | 0.1941 | 0.074* | |
H13B | −0.4087 | 1.0760 | 0.2232 | 0.074* | |
C14 | −0.6763 (4) | 0.9471 (3) | 0.12390 (12) | 0.0775 (7) | |
H14A | −0.6222 | 0.8595 | 0.1311 | 0.116* | |
H14B | −0.7961 | 0.9439 | 0.0958 | 0.116* | |
H14C | −0.7199 | 0.9836 | 0.1575 | 0.116* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0478 (3) | 0.0562 (3) | 0.0501 (3) | 0.0128 (2) | 0.0108 (2) | 0.0024 (2) |
O1 | 0.0706 (10) | 0.0653 (10) | 0.0833 (11) | 0.0294 (9) | −0.0008 (9) | 0.0001 (9) |
O2 | 0.0655 (10) | 0.0948 (13) | 0.0591 (9) | −0.0136 (9) | 0.0169 (8) | −0.0006 (9) |
N1 | 0.0812 (12) | 0.0516 (10) | 0.0446 (9) | −0.0102 (9) | 0.0068 (8) | −0.0004 (8) |
N2 | 0.0644 (12) | 0.0506 (10) | 0.0679 (12) | −0.0186 (9) | 0.0071 (9) | −0.0081 (9) |
N3 | 0.0537 (10) | 0.0539 (11) | 0.0571 (10) | 0.0066 (8) | 0.0065 (8) | 0.0148 (8) |
C1 | 0.0597 (11) | 0.0381 (10) | 0.0460 (10) | −0.0023 (8) | 0.0084 (9) | −0.0042 (8) |
C2 | 0.0565 (11) | 0.0475 (11) | 0.0485 (11) | −0.0015 (9) | 0.0095 (9) | −0.0017 (8) |
C3 | 0.0586 (12) | 0.0545 (12) | 0.0477 (11) | 0.0155 (9) | 0.0124 (9) | −0.0018 (9) |
C4 | 0.0854 (16) | 0.0459 (11) | 0.0538 (12) | 0.0141 (11) | 0.0167 (11) | 0.0050 (9) |
C5 | 0.0802 (15) | 0.0418 (11) | 0.0608 (13) | −0.0044 (10) | 0.0240 (11) | 0.0011 (9) |
C6 | 0.0614 (12) | 0.0387 (10) | 0.0528 (11) | −0.0029 (9) | 0.0149 (9) | −0.0083 (8) |
C7 | 0.0746 (15) | 0.0505 (12) | 0.0609 (13) | −0.0097 (11) | −0.0104 (11) | −0.0039 (10) |
C8 | 0.0708 (13) | 0.0440 (11) | 0.0521 (11) | −0.0130 (10) | −0.0064 (10) | −0.0016 (9) |
C9 | 0.0911 (18) | 0.0631 (14) | 0.0649 (14) | −0.0278 (13) | −0.0192 (13) | 0.0137 (12) |
C10 | 0.0816 (15) | 0.0558 (13) | 0.0532 (12) | −0.0136 (11) | −0.0063 (11) | −0.0013 (10) |
C11 | 0.105 (2) | 0.0846 (19) | 0.0741 (16) | 0.0015 (17) | 0.0253 (15) | −0.0012 (15) |
C12 | 0.102 (2) | 0.0791 (18) | 0.0576 (14) | 0.0026 (15) | −0.0060 (13) | 0.0041 (12) |
C13 | 0.0608 (12) | 0.0718 (14) | 0.0523 (12) | 0.0247 (11) | 0.0086 (10) | 0.0003 (10) |
C14 | 0.0595 (14) | 0.0900 (19) | 0.0836 (18) | −0.0051 (13) | 0.0105 (13) | 0.0222 (15) |
Geometric parameters (Å, º) top
S1—O2 | 1.4212 (17) | C5—C6 | 1.389 (3) |
S1—O1 | 1.4251 (17) | C5—H5 | 0.930 |
S1—N3 | 1.5924 (19) | C7—C8 | 1.361 (3) |
S1—C13 | 1.786 (2) | C7—H7 | 0.930 |
N1—C11 | 1.450 (3) | C8—C9 | 1.504 (3) |
N1—C10 | 1.459 (3) | C9—C10 | 1.478 (3) |
N1—C12 | 1.466 (3) | C9—H9A | 0.970 |
N2—C6 | 1.362 (3) | C9—H9B | 0.970 |
N2—C7 | 1.366 (3) | C10—H10A | 0.970 |
N2—H2N | 0.79 (3) | C10—H10B | 0.970 |
N3—C14 | 1.457 (3) | C11—H11A | 0.960 |
N3—H3N | 0.85 (3) | C11—H11B | 0.960 |
C1—C2 | 1.394 (3) | C11—H11C | 0.960 |
C1—C6 | 1.407 (3) | C12—H12A | 0.960 |
C1—C8 | 1.435 (3) | C12—H12B | 0.960 |
C2—C3 | 1.375 (3) | C12—H12C | 0.960 |
C2—H2 | 0.930 | C13—H13A | 0.970 |
C3—C4 | 1.401 (3) | C13—H13B | 0.970 |
C3—C13 | 1.503 (3) | C14—H14A | 0.960 |
C4—C5 | 1.371 (3) | C14—H14B | 0.960 |
C4—H4 | 0.930 | C14—H14C | 0.960 |
| | | |
O2—S1—O1 | 118.90 (11) | C1—C8—C9 | 124.4 (2) |
O2—S1—N3 | 106.90 (10) | C10—C9—C8 | 115.5 (2) |
O1—S1—N3 | 108.52 (11) | C10—C9—H9A | 108.4 |
O2—S1—C13 | 107.72 (12) | C8—C9—H9A | 108.4 |
O1—S1—C13 | 106.57 (11) | C10—C9—H9B | 108.4 |
N3—S1—C13 | 107.80 (10) | C8—C9—H9B | 108.4 |
C11—N1—C10 | 113.9 (2) | H9A—C9—H9B | 107.5 |
C11—N1—C12 | 110.1 (2) | N1—C10—C9 | 112.78 (19) |
C10—N1—C12 | 109.2 (2) | N1—C10—H10A | 109.0 |
C6—N2—C7 | 108.73 (19) | C9—C10—H10A | 109.0 |
C6—N2—H2N | 126.6 (18) | N1—C10—H10B | 109.0 |
C7—N2—H2N | 123.9 (18) | C9—C10—H10B | 109.0 |
C14—N3—S1 | 121.16 (17) | H10A—C10—H10B | 107.8 |
C14—N3—H3N | 119.5 (16) | N1—C11—H11A | 109.5 |
S1—N3—H3N | 113.0 (16) | N1—C11—H11B | 109.5 |
C2—C1—C6 | 119.27 (19) | H11A—C11—H11B | 109.5 |
C2—C1—C8 | 133.97 (19) | N1—C11—H11C | 109.5 |
C6—C1—C8 | 106.76 (19) | H11A—C11—H11C | 109.5 |
C3—C2—C1 | 119.5 (2) | H11B—C11—H11C | 109.5 |
C3—C2—H2 | 120.2 | N1—C12—H12A | 109.5 |
C1—C2—H2 | 120.2 | N1—C12—H12B | 109.5 |
C2—C3—C4 | 119.9 (2) | H12A—C12—H12B | 109.5 |
C2—C3—C13 | 120.3 (2) | N1—C12—H12C | 109.5 |
C4—C3—C13 | 119.8 (2) | H12A—C12—H12C | 109.5 |
C5—C4—C3 | 122.1 (2) | H12B—C12—H12C | 109.5 |
C5—C4—H4 | 119.0 | C3—C13—S1 | 112.35 (14) |
C3—C4—H4 | 119.0 | C3—C13—H13A | 109.1 |
C4—C5—C6 | 117.6 (2) | S1—C13—H13A | 109.1 |
C4—C5—H5 | 121.2 | C3—C13—H13B | 109.1 |
C6—C5—H5 | 121.2 | S1—C13—H13B | 109.1 |
N2—C6—C5 | 130.6 (2) | H13A—C13—H13B | 107.9 |
N2—C6—C1 | 107.89 (18) | N3—C14—H14A | 109.5 |
C5—C6—C1 | 121.5 (2) | N3—C14—H14B | 109.5 |
C8—C7—N2 | 110.6 (2) | H14A—C14—H14B | 109.5 |
C8—C7—H7 | 124.7 | N3—C14—H14C | 109.5 |
N2—C7—H7 | 124.7 | H14A—C14—H14C | 109.5 |
C7—C8—C1 | 106.0 (2) | H14B—C14—H14C | 109.5 |
C7—C8—C9 | 129.6 (2) | | |
| | | |
O2—S1—N3—C14 | 176.44 (19) | C6—N2—C7—C8 | 0.4 (3) |
O1—S1—N3—C14 | 47.1 (2) | N2—C7—C8—C1 | 0.3 (3) |
C13—S1—N3—C14 | −68.0 (2) | N2—C7—C8—C9 | −179.3 (2) |
C6—C1—C2—C3 | −0.5 (3) | C2—C1—C8—C7 | −180.0 (2) |
C8—C1—C2—C3 | 178.6 (2) | C6—C1—C8—C7 | −0.8 (2) |
C1—C2—C3—C4 | −0.7 (3) | C2—C1—C8—C9 | −0.3 (4) |
C1—C2—C3—C13 | 179.19 (17) | C6—C1—C8—C9 | 178.8 (2) |
C2—C3—C4—C5 | 1.1 (3) | C7—C8—C9—C10 | 3.1 (4) |
C13—C3—C4—C5 | −178.76 (19) | C1—C8—C9—C10 | −176.4 (2) |
C3—C4—C5—C6 | −0.3 (3) | C11—N1—C10—C9 | −78.5 (3) |
C7—N2—C6—C5 | 178.1 (2) | C12—N1—C10—C9 | 158.1 (2) |
C7—N2—C6—C1 | −0.9 (2) | C8—C9—C10—N1 | −179.1 (2) |
C4—C5—C6—N2 | −179.7 (2) | C2—C3—C13—S1 | −100.4 (2) |
C4—C5—C6—C1 | −0.8 (3) | C4—C3—C13—S1 | 79.5 (2) |
C2—C1—C6—N2 | −179.64 (17) | O2—S1—C13—C3 | −64.59 (19) |
C8—C1—C6—N2 | 1.0 (2) | O1—S1—C13—C3 | 64.1 (2) |
C2—C1—C6—C5 | 1.2 (3) | N3—S1—C13—C3 | −179.62 (16) |
C8—C1—C6—C5 | −178.07 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O1i | 0.79 (3) | 2.15 (3) | 2.899 (2) | 158 (2) |
N3—H3N···N1ii | 0.85 (3) | 2.06 (3) | 2.893 (3) | 167 (2) |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x−1/2, y+1/2, −z+1/2. |