Zolmitriptan chloro­form solvate

In the title compound (systematic name: (S)-4-{3-[2-(dimethyl­amino)eth­yl]-1H-indol-5-ylmeth­yl}oxazolidin-2-one chloro­form solvate), C₁₆H₂₁N₃O₂·CHCl₃, 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.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](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

---

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: 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-yl methyl]-2-oxazolidinone. chloroform solvate

Crystal data

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) Å^3	Block, colorless
Z = 4	0.20 × 0.16 × 0.08 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.079	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.243	w = 1/[σ^2(Fo^2) + (0.1384P)^2 + 1.1361P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2^i	0.82 (3)	2.09 (2)	2.884 (5)	165 (4)
N3—H3N···N2^ii	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.