α-{3-[2-(Di­methyl­ammonio)­ethyl]-1H-indol-5-yl}-N-methyl­methanesulfon­amide succinate (sumatriptan succinate)

The title compound, C₁₄H₂₂N₃O₂S⁺·C₄H₅O₄⁻, a well known agonist of the 5-hydroxy­trypt­amine receptor, consists of sumatriptan cations and succinate anions. The ten-membered indole ring system is planar. The succinate moiety is nearly perpendicular to the ethyl­amine side chain, with a (−)­synclinal conformation. The structure is stabilized by O—H...O, C—H...O and C—H...π intermolecular interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.064
• wR factor = 0.158
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found





Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.86

Alert level B
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           28.05
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               4525
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         5040
           Completeness (_total/calc)             89.78%

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         N3
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....        C15

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           28.05
           From the CIF: _reflns_number_total               4525
           From the CIF: _diffrn_reflns_limit_ max hkl   11.   14.   21.
           From the CIF: _diffrn_reflns_limit_ min hkl  -13.  -14.  -21.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   13.   14.   24.
           Calculated minimum hkl  -13.  -14.  -24.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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

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Computing details

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: 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)'; software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

α-{3-[2-(Dimethylammonio)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide (sumatriptan) succinate

Crystal data

C14H22N3O2S^+·C4H5O4^−	F(000) = 880
Mr = 413.49	Dx = 1.321 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.9076 (9) Å	Cell parameters from 2738 reflections
b = 11.2342 (10) Å	θ = 2.8–23.8°
c = 18.7010 (16) Å	µ = 0.19 mm^−1
β = 92.602 (2)°	T = 293 K
V = 2079.3 (3) Å^3	Cubes, colourless
Z = 4	0.21 × 0.20 × 0.18 mm

Data collection

Bruker Smart APEX CCD area-detector diffractometer	3431 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 28.1°, θmin = 2.1°
ω scans	h = −13→11
12456 measured reflections	k = −14→14
4525 independent reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.072P)^2 + 0.603P] where P = (Fo^2 + 2Fc^2)/3
4525 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

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
S1	0.07257 (6)	0.83322 (5)	0.17545 (4)	0.03659 (19)
O1	−0.01500 (19)	0.73739 (18)	0.15476 (11)	0.0534 (5)
O2	0.0708 (2)	0.93553 (18)	0.13051 (12)	0.0619 (6)
O3	0.4193 (3)	0.5607 (2)	0.32896 (14)	0.0750 (8)
O4	0.5084 (2)	0.44690 (18)	0.24719 (11)	0.0560 (5)
O5	0.19980 (19)	0.3020 (2)	0.18001 (10)	0.0566 (6)
O6	0.3803 (2)	0.19826 (17)	0.15821 (11)	0.0576 (6)
N1	0.1160 (2)	0.2409 (2)	0.04499 (13)	0.0420 (5)
N2	0.3995 (2)	0.6487 (2)	−0.09081 (14)	0.0508 (6)
N3	0.0403 (3)	0.8678 (2)	0.25592 (13)	0.0477 (6)
C1	0.3188 (2)	0.6058 (2)	0.01593 (14)	0.0375 (6)
C2	0.2799 (2)	0.6322 (2)	0.08447 (14)	0.0395 (6)
H2	0.2463	0.5725	0.1132	0.047*
C3	0.2910 (2)	0.7475 (2)	0.11008 (15)	0.0415 (6)
C4	0.3435 (3)	0.8372 (2)	0.06647 (16)	0.0465 (7)
H4	0.3516	0.9143	0.0843	0.056*
C5	0.3828 (3)	0.8141 (2)	−0.00145 (16)	0.0467 (7)
H5	0.4179	0.8739	−0.0296	0.056*
C6	0.3686 (2)	0.6983 (2)	−0.02692 (15)	0.0419 (6)
C7	0.3748 (3)	0.5298 (3)	−0.08910 (16)	0.0490 (7)
H7	0.3907	0.4773	−0.1262	0.059*
C8	0.3238 (2)	0.4983 (2)	−0.02565 (15)	0.0425 (6)
C9	0.2917 (3)	0.3755 (2)	−0.00128 (16)	0.0472 (7)
H9A	0.3374	0.3618	0.0450	0.057*
H9B	0.3270	0.3188	−0.0348	0.057*
C10	0.1421 (3)	0.3530 (2)	0.00500 (15)	0.0420 (6)
H10A	0.1022	0.4195	0.0295	0.050*
H10B	0.0991	0.3478	−0.0425	0.050*
C11	−0.0308 (3)	0.2233 (3)	0.05453 (19)	0.0619 (9)
H11A	−0.0765	0.2127	0.0086	0.093*
H11B	−0.0668	0.2918	0.0777	0.093*
H11C	−0.0439	0.1540	0.0835	0.093*
C12	0.1755 (3)	0.1337 (2)	0.01224 (17)	0.0550 (8)
H12A	0.1523	0.0644	0.0391	0.083*
H12B	0.2720	0.1418	0.0127	0.083*
H12C	0.1405	0.1257	−0.0363	0.083*
C13	0.2413 (2)	0.7789 (3)	0.18262 (15)	0.0449 (6)
H13A	0.2997	0.8391	0.2047	0.054*
H13B	0.2451	0.7089	0.2130	0.054*
C14	0.0730 (4)	0.9859 (3)	0.2831 (2)	0.0902 (13)
H14A	0.1627	1.0070	0.2704	0.135*
H14B	0.0683	0.9863	0.3343	0.135*
H14C	0.0098	1.0425	0.2627	0.135*
C15	0.4280 (3)	0.4625 (2)	0.29223 (15)	0.0425 (6)
C16	0.3292 (3)	0.3707 (3)	0.31501 (16)	0.0511 (7)
H16A	0.2384	0.4000	0.3045	0.061*
H16B	0.3401	0.3602	0.3664	0.061*
C17	0.3443 (3)	0.2517 (2)	0.27948 (15)	0.0469 (7)
H17A	0.2885	0.1943	0.3032	0.056*
H17B	0.4375	0.2261	0.2862	0.056*
C18	0.3062 (3)	0.2509 (2)	0.20069 (14)	0.0398 (6)
H1	0.435 (3)	0.681 (3)	−0.1240 (18)	0.054 (9)*
H2A	0.153 (3)	0.254 (2)	0.0882 (17)	0.050 (8)*
H3	−0.031 (4)	0.841 (3)	0.267 (2)	0.074 (11)*
H3A	0.491 (4)	0.608 (3)	0.322 (2)	0.087 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0356 (3)	0.0415 (3)	0.0329 (4)	−0.0018 (2)	0.0040 (2)	0.0000 (3)
O1	0.0491 (11)	0.0636 (12)	0.0473 (13)	−0.0125 (9)	0.0014 (9)	−0.0153 (10)
O2	0.0648 (13)	0.0614 (12)	0.0607 (14)	0.0118 (10)	0.0169 (11)	0.0223 (11)
O3	0.0746 (16)	0.0699 (15)	0.0830 (18)	−0.0204 (12)	0.0322 (14)	−0.0317 (13)
O4	0.0598 (12)	0.0602 (12)	0.0496 (13)	−0.0076 (9)	0.0213 (10)	−0.0013 (10)
O5	0.0406 (10)	0.0946 (16)	0.0345 (12)	0.0141 (10)	0.0013 (8)	0.0026 (10)
O6	0.0696 (14)	0.0568 (12)	0.0467 (13)	0.0193 (10)	0.0071 (10)	0.0002 (10)
N1	0.0429 (13)	0.0531 (13)	0.0297 (14)	−0.0018 (10)	−0.0030 (10)	0.0033 (10)
N2	0.0479 (14)	0.0693 (16)	0.0364 (15)	−0.0086 (11)	0.0142 (11)	0.0044 (12)
N3	0.0466 (14)	0.0567 (14)	0.0407 (15)	−0.0116 (11)	0.0106 (11)	−0.0122 (11)
C1	0.0270 (12)	0.0489 (14)	0.0368 (16)	0.0036 (10)	0.0028 (10)	0.0047 (11)
C2	0.0337 (13)	0.0490 (14)	0.0360 (16)	0.0043 (10)	0.0048 (11)	0.0063 (11)
C3	0.0284 (12)	0.0568 (15)	0.0392 (16)	0.0039 (11)	0.0016 (11)	0.0015 (12)
C4	0.0369 (14)	0.0477 (14)	0.0549 (19)	−0.0032 (11)	0.0033 (12)	−0.0020 (13)
C5	0.0378 (14)	0.0530 (16)	0.0500 (19)	−0.0061 (11)	0.0092 (12)	0.0081 (13)
C6	0.0300 (12)	0.0558 (15)	0.0405 (17)	−0.0015 (11)	0.0068 (11)	0.0067 (12)
C7	0.0463 (15)	0.0609 (17)	0.0405 (17)	−0.0029 (13)	0.0083 (12)	−0.0059 (13)
C8	0.0360 (13)	0.0506 (14)	0.0414 (17)	0.0003 (11)	0.0064 (11)	0.0003 (12)
C9	0.0432 (15)	0.0522 (15)	0.0465 (18)	0.0068 (11)	0.0068 (13)	−0.0005 (13)
C10	0.0449 (14)	0.0446 (14)	0.0360 (16)	0.0013 (11)	−0.0029 (11)	0.0016 (11)
C11	0.0439 (16)	0.080 (2)	0.062 (2)	−0.0086 (14)	0.0036 (15)	0.0053 (17)
C12	0.069 (2)	0.0468 (15)	0.049 (2)	0.0042 (13)	0.0012 (15)	0.0066 (13)
C13	0.0371 (14)	0.0606 (16)	0.0369 (17)	0.0036 (11)	0.0001 (11)	−0.0016 (13)
C14	0.115 (3)	0.074 (2)	0.082 (3)	−0.024 (2)	0.014 (2)	−0.043 (2)
C15	0.0399 (14)	0.0535 (15)	0.0339 (16)	−0.0001 (11)	−0.0002 (12)	−0.0034 (12)
C16	0.0466 (16)	0.0756 (19)	0.0316 (16)	−0.0163 (13)	0.0055 (12)	−0.0060 (14)
C17	0.0504 (16)	0.0551 (15)	0.0347 (17)	−0.0129 (12)	−0.0053 (12)	0.0087 (12)
C18	0.0392 (14)	0.0434 (13)	0.0370 (17)	−0.0051 (11)	0.0042 (11)	0.0047 (11)

Geometric parameters (Å, º)

S1—O2	1.423 (2)	C5—H5	0.9300
S1—O1	1.425 (2)	C7—C8	1.358 (4)
S1—N3	1.601 (2)	C7—H7	0.9300
S1—C13	1.779 (3)	C8—C9	1.491 (4)
O3—C15	1.304 (3)	C9—C10	1.514 (4)
O3—H3A	0.90 (4)	C9—H9A	0.9700
O4—C15	1.199 (3)	C9—H9B	0.9700
O5—C18	1.246 (3)	C10—H10A	0.9700
O6—C18	1.254 (3)	C10—H10B	0.9700
N1—C12	1.484 (4)	C11—H11A	0.9600
N1—C11	1.487 (4)	C11—H11B	0.9600
N1—C10	1.493 (3)	C11—H11C	0.9600
N1—H2A	0.89 (3)	C12—H12A	0.9600
N2—C7	1.358 (4)	C12—H12B	0.9600
N2—C6	1.366 (4)	C12—H12C	0.9600
N2—H1	0.82 (3)	C13—H13A	0.9700
N3—C14	1.452 (4)	C13—H13B	0.9700
N3—H3	0.80 (4)	C14—H14A	0.9600
C1—C2	1.387 (4)	C14—H14B	0.9600
C1—C6	1.415 (3)	C14—H14C	0.9600
C1—C8	1.438 (4)	C15—C16	1.497 (4)
C2—C3	1.384 (4)	C16—C17	1.503 (4)
C2—H2	0.9300	C16—H16A	0.9700
C3—C4	1.410 (4)	C16—H16B	0.9700
C3—C13	1.506 (4)	C17—C18	1.504 (4)
C4—C5	1.370 (4)	C17—H17A	0.9700
C4—H4	0.9300	C17—H17B	0.9700
C5—C6	1.391 (4)
O2—S1—O1	117.3 (1)	N1—C10—C9	111.8 (2)
O2—S1—N3	111.2 (1)	N1—C10—H10A	109.3
O1—S1—N3	107.1 (1)	C9—C10—H10A	109.3
O2—S1—C13	108.0 (1)	N1—C10—H10B	109.3
O1—S1—C13	108.7 (1)	C9—C10—H10B	109.3
N3—S1—C13	103.9 (1)	H10A—C10—H10B	107.9
C15—O3—H3A	111 (2)	N1—C11—H11A	109.5
C12—N1—C11	110.5 (2)	N1—C11—H11B	109.5
C12—N1—C10	113.4 (2)	H11A—C11—H11B	109.5
C11—N1—C10	111.4 (2)	N1—C11—H11C	109.5
C12—N1—H2A	111.1 (19)	H11A—C11—H11C	109.5
C11—N1—H2A	106.1 (19)	H11B—C11—H11C	109.5
C10—N1—H2A	103.9 (19)	N1—C12—H12A	109.5
C7—N2—C6	109.4 (2)	N1—C12—H12B	109.5
C7—N2—H1	123 (2)	H12A—C12—H12B	109.5
C6—N2—H1	127 (2)	N1—C12—H12C	109.5
C14—N3—S1	120.0 (2)	H12A—C12—H12C	109.5
C14—N3—H3	116 (3)	H12B—C12—H12C	109.5
S1—N3—H3	112 (3)	C3—C13—S1	110.90 (18)
C2—C1—C6	119.0 (2)	C3—C13—H13A	109.5
C2—C1—C8	134.2 (2)	S1—C13—H13A	109.5
C6—C1—C8	106.8 (2)	C3—C13—H13B	109.5
C3—C2—C1	119.9 (2)	S1—C13—H13B	109.5
C3—C2—H2	120.0	H13A—C13—H13B	108.0
C1—C2—H2	120.0	N3—C14—H14A	109.5
C2—C3—C4	119.6 (2)	N3—C14—H14B	109.5
C2—C3—C13	120.4 (2)	H14A—C14—H14B	109.5
C4—C3—C13	119.9 (2)	N3—C14—H14C	109.5
C5—C4—C3	121.9 (3)	H14A—C14—H14C	109.5
C5—C4—H4	119.0	H14B—C14—H14C	109.5
C3—C4—H4	119.0	O4—C15—O3	123.8 (3)
C4—C5—C6	117.8 (2)	O4—C15—C16	124.3 (3)
C4—C5—H5	121.1	O3—C15—C16	111.9 (2)
C6—C5—H5	121.1	C15—C16—C17	114.0 (2)
N2—C6—C5	131.2 (2)	C15—C16—H16A	108.7
N2—C6—C1	107.1 (2)	C17—C16—H16A	108.7
C5—C6—C1	121.7 (3)	C15—C16—H16B	108.7
C8—C7—N2	110.6 (3)	C17—C16—H16B	108.7
C8—C7—H7	124.7	H16A—C16—H16B	107.6
N2—C7—H7	124.7	C16—C17—C18	114.4 (2)
C7—C8—C1	106.1 (2)	C16—C17—H17A	108.7
C7—C8—C9	126.9 (3)	C18—C17—H17A	108.7
C1—C8—C9	126.7 (2)	C16—C17—H17B	108.7
C8—C9—C10	113.6 (2)	C18—C17—H17B	108.7
C8—C9—H9A	108.8	H17A—C17—H17B	107.6
C10—C9—H9A	108.8	O5—C18—O6	122.1 (3)
C8—C9—H9B	108.8	O5—C18—C17	118.2 (2)
C10—C9—H9B	108.8	O6—C18—C17	119.7 (2)
H9A—C9—H9B	107.7
O2—S1—N3—C14	−27.7 (3)	N2—C7—C8—C9	−175.9 (3)
O1—S1—N3—C14	−157.0 (3)	C2—C1—C8—C7	−178.5 (3)
C13—S1—N3—C14	88.1 (3)	C6—C1—C8—C7	0.2 (3)
C6—C1—C2—C3	−0.4 (4)	C2—C1—C8—C9	−3.8 (5)
C8—C1—C2—C3	178.2 (3)	C6—C1—C8—C9	174.9 (2)
C1—C2—C3—C4	−0.8 (4)	C7—C8—C9—C10	−112.1 (3)
C1—C2—C3—C13	176.3 (2)	C1—C8—C9—C10	74.2 (4)
C2—C3—C4—C5	0.7 (4)	C12—N1—C10—C9	−58.0 (3)
C13—C3—C4—C5	−176.3 (2)	C11—N1—C10—C9	176.7 (2)
C3—C4—C5—C6	0.5 (4)	C8—C9—C10—N1	−166.9 (2)
C7—N2—C6—C5	176.3 (3)	C2—C3—C13—S1	−93.9 (3)
C7—N2—C6—C1	−1.6 (3)	C4—C3—C13—S1	83.1 (3)
C4—C5—C6—N2	−179.3 (3)	O2—S1—C13—C3	−59.0 (2)
C4—C5—C6—C1	−1.7 (4)	O1—S1—C13—C3	69.1 (2)
C2—C1—C6—N2	179.8 (2)	N3—S1—C13—C3	−177.14 (19)
C8—C1—C6—N2	0.9 (3)	O4—C15—C16—C17	3.6 (4)
C2—C1—C6—C5	1.6 (4)	O3—C15—C16—C17	−174.2 (3)
C8—C1—C6—C5	−177.3 (2)	C15—C16—C17—C18	−68.5 (3)
C6—N2—C7—C8	1.8 (3)	C16—C17—C18—O5	−45.0 (3)
N2—C7—C8—C1	−1.2 (3)	C16—C17—C18—O6	135.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2A···O5	0.88 (3)	1.84 (3)	2.710 (3)	168 (3)
N2—H1···O6^i	0.81 (3)	2.39 (3)	3.091 (3)	145 (3)
O3—H3A···O6^ii	0.90 (4)	1.66 (4)	2.519 (3)	159 (4)
N3—H3···O5^iii	0.80 (4)	2.03 (4)	2.811 (3)	164 (4)
C10—H10B···O1^iv	0.97	2.42	3.347 (3)	160
C12—H12A···O2^v	0.96	2.41	3.337 (4)	163
C13—H13A···O4^ii	0.97	2.39	3.337 (4)	164

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x, −y+1, −z; (v) x, y−1, z.