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Sumatriptan, {3-[2-(dimethyl­amino)eth­yl]-1H-indol-5-yl}-N-methyl­methane­sulfonamide, C14H21N3O2S, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806005101/cf6494sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806005101/cf6494Isup2.hkl
Contains datablock I

CCDC reference: 601136

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](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

Computing details top

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]-1H-indol-5-yl}-N-methylmethanesulfonamide top
Crystal data top
C14H21N3O2SF(000) = 632
Mr = 295.40Dx = 1.276 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7659 reflections
a = 6.3216 (3) Åθ = 2.1–27.9°
b = 10.1290 (5) ŵ = 0.22 mm1
c = 24.1541 (12) ÅT = 273 K
β = 96.318 (1)°Needle, yellow
V = 1537.23 (13) Å30.22 × 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 tubeRint = 0.021
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
ω scansh = 77
14386 measured reflectionsk = 1212
2709 independent reflectionsl = 2828
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H 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 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.25 e Å3
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
xyzUiso*/Ueq
S10.28124 (8)1.04034 (5)0.13908 (2)0.0510 (2)
O10.2090 (3)0.91058 (17)0.15409 (7)0.0737 (5)
O20.1550 (3)1.12094 (19)0.10749 (7)0.0724 (5)
N10.1766 (3)0.73779 (18)0.46980 (7)0.0591 (5)
N20.4624 (3)1.16874 (19)0.33896 (8)0.0610 (5)
H2N0.557 (4)1.221 (3)0.3423 (10)0.061 (7)*
N30.5103 (3)1.02963 (19)0.10463 (8)0.0549 (5)
H3N0.545 (4)1.098 (3)0.0856 (10)0.060 (7)*
C10.1452 (3)1.07415 (19)0.31524 (8)0.0477 (5)
C20.0497 (3)1.0584 (2)0.28283 (8)0.0506 (5)
H20.14300.99220.29120.061*
C30.1029 (3)1.1415 (2)0.23849 (8)0.0531 (5)
C40.0374 (4)1.2421 (2)0.22654 (9)0.0610 (6)
H40.00191.29850.19680.073*
C50.2309 (4)1.2598 (2)0.25731 (9)0.0597 (6)
H50.32281.32670.24880.072*
C60.2846 (3)1.17445 (19)0.30164 (8)0.0503 (5)
C70.4381 (4)1.0695 (2)0.37603 (10)0.0633 (6)
H70.53831.04680.40560.076*
C80.2470 (4)1.0086 (2)0.36368 (9)0.0566 (5)
C90.1506 (4)0.8961 (3)0.39287 (10)0.0751 (7)
H9A0.01220.92370.40240.090*
H9B0.12800.82290.36700.090*
C100.2771 (4)0.8482 (2)0.44404 (9)0.0645 (6)
H10A0.41640.82090.43500.077*
H10B0.29740.92020.47060.077*
C110.0053 (5)0.7766 (3)0.50167 (12)0.0869 (8)
H11A0.05880.83710.53040.130*
H11B0.05090.69980.51820.130*
H11C0.10530.81850.47750.130*
C120.3391 (5)0.6643 (3)0.50525 (11)0.0807 (8)
H12A0.40000.72020.53490.121*
H12B0.44870.63570.48340.121*
H12C0.27510.58870.52070.121*
C130.3111 (4)1.1250 (2)0.20261 (9)0.0614 (6)
H13A0.37271.21130.19410.074*
H13B0.40871.07600.22320.074*
C140.6763 (4)0.9471 (3)0.12390 (12)0.0775 (7)
H14A0.62220.85950.13110.116*
H14B0.79610.94390.09580.116*
H14C0.71990.98360.15750.116*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0478 (3)0.0562 (3)0.0501 (3)0.0128 (2)0.0108 (2)0.0024 (2)
O10.0706 (10)0.0653 (10)0.0833 (11)0.0294 (9)0.0008 (9)0.0001 (9)
O20.0655 (10)0.0948 (13)0.0591 (9)0.0136 (9)0.0169 (8)0.0006 (9)
N10.0812 (12)0.0516 (10)0.0446 (9)0.0102 (9)0.0068 (8)0.0004 (8)
N20.0644 (12)0.0506 (10)0.0679 (12)0.0186 (9)0.0071 (9)0.0081 (9)
N30.0537 (10)0.0539 (11)0.0571 (10)0.0066 (8)0.0065 (8)0.0148 (8)
C10.0597 (11)0.0381 (10)0.0460 (10)0.0023 (8)0.0084 (9)0.0042 (8)
C20.0565 (11)0.0475 (11)0.0485 (11)0.0015 (9)0.0095 (9)0.0017 (8)
C30.0586 (12)0.0545 (12)0.0477 (11)0.0155 (9)0.0124 (9)0.0018 (9)
C40.0854 (16)0.0459 (11)0.0538 (12)0.0141 (11)0.0167 (11)0.0050 (9)
C50.0802 (15)0.0418 (11)0.0608 (13)0.0044 (10)0.0240 (11)0.0011 (9)
C60.0614 (12)0.0387 (10)0.0528 (11)0.0029 (9)0.0149 (9)0.0083 (8)
C70.0746 (15)0.0505 (12)0.0609 (13)0.0097 (11)0.0104 (11)0.0039 (10)
C80.0708 (13)0.0440 (11)0.0521 (11)0.0130 (10)0.0064 (10)0.0016 (9)
C90.0911 (18)0.0631 (14)0.0649 (14)0.0278 (13)0.0192 (13)0.0137 (12)
C100.0816 (15)0.0558 (13)0.0532 (12)0.0136 (11)0.0063 (11)0.0013 (10)
C110.105 (2)0.0846 (19)0.0741 (16)0.0015 (17)0.0253 (15)0.0012 (15)
C120.102 (2)0.0791 (18)0.0576 (14)0.0026 (15)0.0060 (13)0.0041 (12)
C130.0608 (12)0.0718 (14)0.0523 (12)0.0247 (11)0.0086 (10)0.0003 (10)
C140.0595 (14)0.0900 (19)0.0836 (18)0.0051 (13)0.0105 (13)0.0222 (15)
Geometric parameters (Å, º) top
S1—O21.4212 (17)C5—C61.389 (3)
S1—O11.4251 (17)C5—H50.930
S1—N31.5924 (19)C7—C81.361 (3)
S1—C131.786 (2)C7—H70.930
N1—C111.450 (3)C8—C91.504 (3)
N1—C101.459 (3)C9—C101.478 (3)
N1—C121.466 (3)C9—H9A0.970
N2—C61.362 (3)C9—H9B0.970
N2—C71.366 (3)C10—H10A0.970
N2—H2N0.79 (3)C10—H10B0.970
N3—C141.457 (3)C11—H11A0.960
N3—H3N0.85 (3)C11—H11B0.960
C1—C21.394 (3)C11—H11C0.960
C1—C61.407 (3)C12—H12A0.960
C1—C81.435 (3)C12—H12B0.960
C2—C31.375 (3)C12—H12C0.960
C2—H20.930C13—H13A0.970
C3—C41.401 (3)C13—H13B0.970
C3—C131.503 (3)C14—H14A0.960
C4—C51.371 (3)C14—H14B0.960
C4—H40.930C14—H14C0.960
O2—S1—O1118.90 (11)C1—C8—C9124.4 (2)
O2—S1—N3106.90 (10)C10—C9—C8115.5 (2)
O1—S1—N3108.52 (11)C10—C9—H9A108.4
O2—S1—C13107.72 (12)C8—C9—H9A108.4
O1—S1—C13106.57 (11)C10—C9—H9B108.4
N3—S1—C13107.80 (10)C8—C9—H9B108.4
C11—N1—C10113.9 (2)H9A—C9—H9B107.5
C11—N1—C12110.1 (2)N1—C10—C9112.78 (19)
C10—N1—C12109.2 (2)N1—C10—H10A109.0
C6—N2—C7108.73 (19)C9—C10—H10A109.0
C6—N2—H2N126.6 (18)N1—C10—H10B109.0
C7—N2—H2N123.9 (18)C9—C10—H10B109.0
C14—N3—S1121.16 (17)H10A—C10—H10B107.8
C14—N3—H3N119.5 (16)N1—C11—H11A109.5
S1—N3—H3N113.0 (16)N1—C11—H11B109.5
C2—C1—C6119.27 (19)H11A—C11—H11B109.5
C2—C1—C8133.97 (19)N1—C11—H11C109.5
C6—C1—C8106.76 (19)H11A—C11—H11C109.5
C3—C2—C1119.5 (2)H11B—C11—H11C109.5
C3—C2—H2120.2N1—C12—H12A109.5
C1—C2—H2120.2N1—C12—H12B109.5
C2—C3—C4119.9 (2)H12A—C12—H12B109.5
C2—C3—C13120.3 (2)N1—C12—H12C109.5
C4—C3—C13119.8 (2)H12A—C12—H12C109.5
C5—C4—C3122.1 (2)H12B—C12—H12C109.5
C5—C4—H4119.0C3—C13—S1112.35 (14)
C3—C4—H4119.0C3—C13—H13A109.1
C4—C5—C6117.6 (2)S1—C13—H13A109.1
C4—C5—H5121.2C3—C13—H13B109.1
C6—C5—H5121.2S1—C13—H13B109.1
N2—C6—C5130.6 (2)H13A—C13—H13B107.9
N2—C6—C1107.89 (18)N3—C14—H14A109.5
C5—C6—C1121.5 (2)N3—C14—H14B109.5
C8—C7—N2110.6 (2)H14A—C14—H14B109.5
C8—C7—H7124.7N3—C14—H14C109.5
N2—C7—H7124.7H14A—C14—H14C109.5
C7—C8—C1106.0 (2)H14B—C14—H14C109.5
C7—C8—C9129.6 (2)
O2—S1—N3—C14176.44 (19)C6—N2—C7—C80.4 (3)
O1—S1—N3—C1447.1 (2)N2—C7—C8—C10.3 (3)
C13—S1—N3—C1468.0 (2)N2—C7—C8—C9179.3 (2)
C6—C1—C2—C30.5 (3)C2—C1—C8—C7180.0 (2)
C8—C1—C2—C3178.6 (2)C6—C1—C8—C70.8 (2)
C1—C2—C3—C40.7 (3)C2—C1—C8—C90.3 (4)
C1—C2—C3—C13179.19 (17)C6—C1—C8—C9178.8 (2)
C2—C3—C4—C51.1 (3)C7—C8—C9—C103.1 (4)
C13—C3—C4—C5178.76 (19)C1—C8—C9—C10176.4 (2)
C3—C4—C5—C60.3 (3)C11—N1—C10—C978.5 (3)
C7—N2—C6—C5178.1 (2)C12—N1—C10—C9158.1 (2)
C7—N2—C6—C10.9 (2)C8—C9—C10—N1179.1 (2)
C4—C5—C6—N2179.7 (2)C2—C3—C13—S1100.4 (2)
C4—C5—C6—C10.8 (3)C4—C3—C13—S179.5 (2)
C2—C1—C6—N2179.64 (17)O2—S1—C13—C364.59 (19)
C8—C1—C6—N21.0 (2)O1—S1—C13—C364.1 (2)
C2—C1—C6—C51.2 (3)N3—S1—C13—C3179.62 (16)
C8—C1—C6—C5178.07 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O1i0.79 (3)2.15 (3)2.899 (2)158 (2)
N3—H3N···N1ii0.85 (3)2.06 (3)2.893 (3)167 (2)
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z+1/2.
 

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