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Zolmitriptan, C16H21N3O2, a selective serotonin (5-HT) receptor agonist, is chemically designated as (S)-4-{3-[2-(dimethyl­amino)eth­yl]-1H-indol-5-ylmeth­yl}oxazolidin-2-one. The mol­ecular geometry is similar to that of sumatriptan, but the two differ in their side-chain orientations. Inter­molecular N—H...O and N—H...N hydrogen bonds form a screw-symmetric helical chain along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011439/er2030sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011439/er2030Isup2.hkl
Contains datablock I

CCDC reference: 642977

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.040
  • wR factor = 0.107
  • Data-to-parameter ratio = 7.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.75 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
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 1549 Count of symmetry unique reflns 1550 Completeness (_total/calc) 99.94% 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 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K 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 3 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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: PLATON (Spek, 2003) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97.

(S)-4-{3-[2-(dimethylamino)ethyl]-1H-indol-5-ylmethyl}oxazolidin-2-one top
Crystal data top
C16H21N3O2F(000) = 616
Mr = 287.36Dx = 1.260 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5206 reflections
a = 9.0643 (7) Åθ = 2.3–26.1°
b = 11.4220 (9) ŵ = 0.09 mm1
c = 14.6320 (12) ÅT = 293 K
V = 1514.9 (2) Å3Block, colourless
Z = 40.19 × 0.17 × 0.12 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1475 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 25.0°, θmin = 2.3°
ω scansh = 1010
10937 measured reflectionsk = 1313
1549 independent reflectionsl = 1717
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0671P)2 + 0.1659P]
where P = (Fo2 + 2Fc2)/3
1549 reflections(Δ/σ)max < 0.001
200 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.11 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
C10.2900 (3)1.0570 (2)1.00847 (16)0.0541 (6)
H10.23421.11631.03490.065*
C20.2334 (3)0.9655 (2)0.96041 (16)0.0474 (6)
C30.3572 (2)0.8950 (2)0.93382 (14)0.0405 (5)
C40.3732 (3)0.7919 (2)0.88279 (15)0.0427 (5)
H40.29000.75340.86090.051*
C50.5119 (3)0.74708 (19)0.86478 (15)0.0435 (5)
C60.6368 (3)0.8041 (2)0.90192 (16)0.0479 (6)
H60.72990.77280.89100.057*
C70.6255 (3)0.9042 (2)0.95350 (16)0.0478 (6)
H70.70870.94010.97790.057*
C80.4851 (3)0.9500 (2)0.96800 (14)0.0430 (5)
C90.0744 (3)0.9408 (3)0.9392 (2)0.0574 (7)
H9A0.01320.99110.97680.069*
H9B0.05270.86040.95580.069*
C100.0321 (3)0.9592 (2)0.8388 (2)0.0572 (7)
H10A0.10050.91560.80090.069*
H10B0.06540.92670.82890.069*
C110.0846 (4)1.1466 (3)0.8544 (3)0.0810 (10)
H11A0.17751.10770.84600.122*
H11B0.08981.22380.82860.122*
H11C0.06301.15210.91840.122*
C120.0067 (4)1.0878 (3)0.7103 (2)0.0825 (10)
H12A0.08001.04250.67880.124*
H12B0.01341.16810.69130.124*
H12C0.08961.05800.69600.124*
C130.5292 (3)0.6397 (2)0.80671 (17)0.0501 (6)
H13A0.43950.59370.81130.060*
H13B0.60890.59290.83160.060*
C140.5611 (3)0.6623 (2)0.70485 (16)0.0472 (6)
H140.55680.58780.67180.057*
C150.4589 (3)0.7498 (3)0.65801 (18)0.0592 (7)
H15A0.39290.70970.61620.071*
H15B0.40010.79120.70300.071*
C160.6936 (3)0.8032 (2)0.62663 (19)0.0591 (7)
N10.4406 (3)1.0495 (2)1.01252 (15)0.0525 (5)
H1N0.496 (3)1.091 (2)1.037 (2)0.056 (9)*
N20.0317 (2)1.08013 (18)0.80867 (14)0.0492 (5)
N30.7028 (2)0.7173 (2)0.68729 (14)0.0501 (5)
H3N0.779 (4)0.676 (3)0.687 (2)0.059 (8)*
O10.5508 (2)0.8291 (2)0.60966 (17)0.0764 (6)
O20.7915 (3)0.8552 (2)0.58831 (19)0.0956 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0599 (15)0.0570 (14)0.0453 (12)0.0132 (12)0.0087 (12)0.0006 (11)
C20.0467 (12)0.0540 (14)0.0417 (11)0.0076 (11)0.0048 (10)0.0067 (11)
C30.0351 (11)0.0471 (12)0.0392 (10)0.0002 (9)0.0018 (9)0.0072 (9)
C40.0368 (11)0.0471 (12)0.0443 (11)0.0053 (10)0.0004 (10)0.0055 (10)
C50.0451 (12)0.0445 (12)0.0409 (11)0.0005 (10)0.0048 (10)0.0080 (9)
C60.0355 (11)0.0575 (14)0.0507 (12)0.0049 (11)0.0046 (11)0.0073 (11)
C70.0373 (11)0.0574 (14)0.0485 (12)0.0072 (11)0.0048 (11)0.0044 (11)
C80.0452 (12)0.0490 (11)0.0349 (10)0.0010 (11)0.0007 (9)0.0034 (9)
C90.0419 (13)0.0641 (16)0.0663 (16)0.0081 (12)0.0119 (12)0.0111 (13)
C100.0400 (13)0.0591 (15)0.0726 (16)0.0019 (12)0.0019 (12)0.0073 (13)
C110.0647 (19)0.074 (2)0.104 (2)0.0211 (17)0.0151 (18)0.0026 (19)
C120.078 (2)0.106 (2)0.0630 (17)0.016 (2)0.0151 (16)0.0047 (18)
C130.0507 (13)0.0442 (12)0.0554 (13)0.0004 (11)0.0063 (12)0.0065 (10)
C140.0459 (13)0.0477 (12)0.0480 (12)0.0035 (10)0.0026 (11)0.0045 (10)
C150.0453 (14)0.0804 (19)0.0518 (13)0.0064 (13)0.0007 (11)0.0049 (13)
C160.0539 (15)0.0577 (15)0.0659 (16)0.0037 (13)0.0004 (13)0.0094 (13)
N10.0578 (12)0.0539 (12)0.0457 (11)0.0020 (11)0.0032 (10)0.0094 (10)
N20.0408 (10)0.0568 (12)0.0499 (10)0.0011 (9)0.0024 (9)0.0035 (9)
N30.0396 (10)0.0584 (12)0.0524 (11)0.0087 (10)0.0048 (10)0.0029 (10)
O10.0597 (12)0.0765 (13)0.0929 (14)0.0059 (10)0.0084 (11)0.0356 (12)
O20.0720 (14)0.0914 (16)0.123 (2)0.0205 (13)0.0075 (14)0.0423 (15)
Geometric parameters (Å, º) top
C1—C21.360 (4)C11—N21.461 (4)
C1—N11.369 (4)C11—H11A0.9600
C1—H10.9300C11—H11B0.9600
C2—C31.435 (3)C11—H11C0.9600
C2—C91.501 (4)C12—N21.460 (4)
C3—C41.402 (3)C12—H12A0.9600
C3—C81.411 (3)C12—H12B0.9600
C4—C51.383 (3)C12—H12C0.9600
C4—H40.9300C13—C141.540 (3)
C5—C61.415 (3)C13—H13A0.9700
C5—C131.500 (3)C13—H13B0.9700
C6—C71.374 (3)C14—N31.453 (3)
C6—H60.9300C14—C151.525 (4)
C7—C81.392 (3)C14—H140.9800
C7—H70.9300C15—O11.419 (3)
C8—N11.370 (3)C15—H15A0.9700
C9—C101.532 (4)C15—H15B0.9700
C9—H9A0.9700C16—O21.207 (3)
C9—H9B0.9700C16—N31.325 (3)
C10—N21.450 (3)C16—O11.351 (3)
C10—H10A0.9700N1—H1N0.78 (3)
C10—H10B0.9700N3—H3N0.83 (3)
C2—C1—N1110.5 (2)H11A—C11—H11C109.5
C2—C1—H1124.7H11B—C11—H11C109.5
N1—C1—H1124.7N2—C12—H12A109.5
C1—C2—C3106.0 (2)N2—C12—H12B109.5
C1—C2—C9127.9 (2)H12A—C12—H12B109.5
C3—C2—C9126.1 (2)N2—C12—H12C109.5
C4—C3—C8118.5 (2)H12A—C12—H12C109.5
C4—C3—C2134.2 (2)H12B—C12—H12C109.5
C8—C3—C2107.3 (2)C5—C13—C14115.49 (19)
C5—C4—C3120.5 (2)C5—C13—H13A108.4
C5—C4—H4119.8C14—C13—H13A108.4
C3—C4—H4119.8C5—C13—H13B108.4
C4—C5—C6118.9 (2)C14—C13—H13B108.4
C4—C5—C13120.3 (2)H13A—C13—H13B107.5
C6—C5—C13120.7 (2)N3—C14—C15100.0 (2)
C7—C6—C5122.3 (2)N3—C14—C13114.2 (2)
C7—C6—H6118.8C15—C14—C13115.5 (2)
C5—C6—H6118.8N3—C14—H14108.9
C6—C7—C8117.7 (2)C15—C14—H14108.9
C6—C7—H7121.2C13—C14—H14108.9
C8—C7—H7121.2O1—C15—C14106.6 (2)
N1—C8—C7130.8 (2)O1—C15—H15A110.4
N1—C8—C3107.2 (2)C14—C15—H15A110.4
C7—C8—C3122.0 (2)O1—C15—H15B110.4
C2—C9—C10114.4 (2)C14—C15—H15B110.4
C2—C9—H9A108.7H15A—C15—H15B108.6
C10—C9—H9A108.7O2—C16—N3129.0 (3)
C2—C9—H9B108.7O2—C16—O1120.8 (3)
C10—C9—H9B108.7N3—C16—O1110.2 (2)
H9A—C9—H9B107.6C1—N1—C8109.0 (2)
N2—C10—C9115.0 (2)C1—N1—H1N129 (2)
N2—C10—H10A108.5C8—N1—H1N122 (2)
C9—C10—H10A108.5C10—N2—C12110.9 (2)
N2—C10—H10B108.5C10—N2—C11111.0 (2)
C9—C10—H10B108.5C12—N2—C11108.0 (3)
H10A—C10—H10B107.5C16—N3—C14112.5 (2)
N2—C11—H11A109.5C16—N3—H3N118 (2)
N2—C11—H11B109.5C14—N3—H3N119 (2)
H11A—C11—H11B109.5C16—O1—C15109.3 (2)
N2—C11—H11C109.5
N1—C1—C2—C30.9 (3)C3—C2—C9—C1071.7 (4)
N1—C1—C2—C9179.5 (3)C2—C9—C10—N269.6 (3)
C1—C2—C3—C4178.7 (2)C4—C5—C13—C1495.6 (3)
C9—C2—C3—C41.7 (4)C6—C5—C13—C1484.4 (3)
C1—C2—C3—C80.3 (2)C5—C13—C14—N365.8 (3)
C9—C2—C3—C8179.9 (2)C5—C13—C14—C1549.5 (3)
C8—C3—C4—C51.5 (3)N3—C14—C15—O18.7 (2)
C2—C3—C4—C5176.8 (2)C13—C14—C15—O1131.8 (2)
C3—C4—C5—C62.7 (3)C2—C1—N1—C81.2 (3)
C3—C4—C5—C13177.31 (19)C7—C8—N1—C1180.0 (2)
C4—C5—C6—C71.6 (3)C3—C8—N1—C11.0 (3)
C13—C5—C6—C7178.4 (2)C9—C10—N2—C12173.5 (2)
C5—C6—C7—C80.6 (3)C9—C10—N2—C1166.4 (3)
C6—C7—C8—N1177.0 (2)O2—C16—N3—C14169.1 (3)
C6—C7—C8—C31.9 (3)O1—C16—N3—C1410.6 (3)
C4—C3—C8—N1178.27 (18)C15—C14—N3—C1611.8 (3)
C2—C3—C8—N10.4 (2)C13—C14—N3—C16135.8 (2)
C4—C3—C8—C70.8 (3)O2—C16—O1—C15175.7 (3)
C2—C3—C8—C7179.5 (2)N3—C16—O1—C154.0 (3)
C1—C2—C9—C10108.8 (3)C14—C15—O1—C163.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.78 (3)2.16 (3)2.883 (3)155 (3)
N3—H3N···N2ii0.83 (3)2.04 (3)2.873 (3)177 (3)
Symmetry codes: (i) x+3/2, y+2, z+1/2; (ii) x+1, y1/2, z+3/2.
 

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