Gelsevirine hydro­chloride

Han, H.-B.; Yuan, Z.; Xiao, K.; Chen, M.-Q.; Zhang, L.

doi:10.1107/S1600536807006393

Gelsevirine hydrochloride

H.-B. Han, Z. Yuan, K. Xiao, M.-Q. Chen and L. Zhang

At 293 K, a crystalline terpenoid indole alkaloid, the title compound, C₂₁H₂₅N₂O₃⁺·Cl⁻, has been isolated from Gelsemium elegans Benth, a Chinese folk medicine plant. Structural ambiguities have been resolved by the X-ray crystallographic analysis. Intramolecular C—H

O and intermolecular C—H

Cl, C—H

O and N—H

Cl hydrogen bonds help to stabilize the structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006393/wn2113sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006393/wn2113Isup2.hkl Contains datablock I

CCDC reference: 640516

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.049
wR factor = 0.109
Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.11 Ratio

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.28 Ratio
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11    ..  CL1     ..       2.92 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  CL1     ..       2.86 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20C   ..  O2      ..       2.86 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4     ..  O1      ..       2.86 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16    ..  CL1     ..       2.85 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21B   ..  CL1     ..       2.86 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20B   ..  O2      ..       2.66 Ang.

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           27.15
           From the CIF: _reflns_number_total               4177
           Count of symmetry unique reflns         2495
           Completeness (_total/calc)            167.41%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1682
           Fraction of Friedel pairs measured     0.674
           Are heavy atom types Z>Si present        yes
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 N2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16    = .          S

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

  11 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
   1 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Gelsevirine hydrochloride top

Crystal data top

C₂₁H₂₅N₂O₃⁺·Cl⁻	F(000) = 824
M_r = 388.88	D_x = 1.332 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 859 reflections
a = 7.398 (3) Å	θ = 2.7–22.9°
b = 8.953 (4) Å	µ = 0.22 mm⁻¹
c = 29.282 (13) Å	T = 293 K
V = 1939.6 (15) Å³	Prism, colorless
Z = 4	0.15 × 0.12 × 0.10 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4177 independent reflections
Radiation source: fine-focus sealed tube	3473 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 27.2°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→6
T_min = 0.968, T_max = 0.978	k = −11→11
9516 measured reflections	l = −37→34

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.053P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4177 reflections	Δρ_max = 0.29 e Å⁻³
250 parameters	Δρ_min = −0.18 e Å⁻³
1 restraint	Absolute structure: Flack, (1983), 1682 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (8)

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.

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	1.0862 (3)	0.5323 (2)	0.00019 (6)	0.0547 (5)
O2	0.8021 (3)	0.4045 (2)	0.04886 (7)	0.0591 (5)
O3	0.5814 (2)	0.80741 (17)	0.11407 (6)	0.0398 (4)
N1	1.0311 (3)	0.5740 (2)	0.04401 (7)	0.0417 (5)
N2	0.8032 (3)	0.5402 (2)	0.22843 (7)	0.0370 (5)
H2X	0.924 (2)	0.536 (3)	0.2291 (8)	0.038 (7)*
C1	0.9659 (3)	0.8895 (3)	0.11657 (9)	0.0388 (6)
H1	0.8909	0.9145	0.1409	0.047*
C2	1.0952 (3)	0.9898 (3)	0.10129 (9)	0.0452 (6)
H2	1.1057	1.0824	0.1154	0.054*
C3	1.2093 (4)	0.9543 (3)	0.06530 (9)	0.0479 (7)
H3	1.2948	1.0233	0.0555	0.057*
C4	1.1966 (4)	0.8172 (3)	0.04401 (9)	0.0443 (6)
H4	1.2727	0.7919	0.0199	0.053*
C5	1.0678 (3)	0.7199 (3)	0.05964 (8)	0.0341 (5)
C6	0.9490 (3)	0.7517 (3)	0.09540 (8)	0.0321 (5)
C7	0.8179 (3)	0.6223 (2)	0.10176 (7)	0.0316 (5)
C8	0.8767 (3)	0.5150 (3)	0.06244 (8)	0.0390 (6)
C9	0.6184 (3)	0.6701 (3)	0.09147 (8)	0.0352 (5)
H9	0.6073	0.6869	0.0585	0.042*
C10	0.4867 (3)	0.5492 (3)	0.10475 (9)	0.0402 (6)
H10A	0.5040	0.4623	0.0854	0.048*
H10B	0.3638	0.5845	0.1007	0.048*
C11	0.5186 (3)	0.5068 (3)	0.15512 (8)	0.0360 (5)
H11	0.4154	0.4527	0.1680	0.043*
C12	0.6952 (4)	0.4180 (2)	0.15995 (8)	0.0347 (5)
C13	0.8339 (3)	0.5461 (2)	0.14920 (7)	0.0292 (5)
H13	0.9580	0.5122	0.1547	0.035*
C14	0.5006 (3)	0.7919 (3)	0.15785 (9)	0.0419 (6)
H14A	0.3702	0.7896	0.1544	0.050*
H14B	0.5310	0.8783	0.1763	0.050*
C15	0.5608 (3)	0.6524 (3)	0.18243 (8)	0.0341 (5)
H15	0.5015	0.6475	0.2123	0.041*
C16	0.7672 (3)	0.6441 (2)	0.18902 (8)	0.0302 (5)
H16	0.8272	0.7413	0.1914	0.036*
C17	0.7312 (4)	0.3923 (3)	0.21137 (9)	0.0421 (6)
H17A	0.6206	0.3655	0.2272	0.051*
H17B	0.8194	0.3134	0.2158	0.051*
C18	0.7057 (4)	0.2692 (3)	0.13617 (9)	0.0457 (6)
H18	0.8196	0.2351	0.1277	0.055*
C19	0.5681 (5)	0.1846 (3)	0.12657 (10)	0.0605 (9)
H19A	0.4520	0.2149	0.1345	0.073*
H19B	0.5857	0.0939	0.1118	0.073*
C20	1.2108 (6)	0.4113 (5)	0.00184 (13)	0.0959 (14)
H20A	1.3193	0.4428	0.0170	0.144*
H20B	1.2393	0.3800	−0.0287	0.144*
H20C	1.1578	0.3295	0.0183	0.144*
C21	0.7370 (4)	0.5884 (3)	0.27428 (8)	0.0504 (7)
H21A	0.6081	0.5770	0.2757	0.076*
H21B	0.7681	0.6912	0.2792	0.076*
H21C	0.7923	0.5279	0.2975	0.076*
Cl1	0.19674 (9)	0.49492 (8)	0.25005 (2)	0.05108 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0553 (11)	0.0756 (14)	0.0331 (10)	0.0160 (11)	0.0032 (8)	−0.0144 (9)
O2	0.0756 (14)	0.0492 (11)	0.0523 (12)	−0.0117 (12)	0.0097 (11)	−0.0217 (10)
O3	0.0429 (10)	0.0302 (8)	0.0464 (10)	0.0063 (8)	0.0016 (8)	0.0048 (8)
N1	0.0430 (13)	0.0506 (13)	0.0314 (11)	0.0082 (10)	0.0047 (9)	−0.0070 (10)
N2	0.0411 (12)	0.0353 (11)	0.0346 (11)	−0.0043 (10)	−0.0007 (9)	0.0052 (8)
C1	0.0393 (14)	0.0363 (13)	0.0408 (14)	−0.0002 (11)	0.0048 (11)	0.0008 (11)
C2	0.0455 (14)	0.0369 (13)	0.0530 (16)	−0.0044 (14)	−0.0015 (12)	0.0016 (13)
C3	0.0384 (14)	0.0521 (16)	0.0531 (16)	−0.0127 (13)	−0.0009 (13)	0.0163 (13)
C4	0.0311 (13)	0.0656 (18)	0.0361 (13)	0.0024 (14)	0.0037 (11)	0.0084 (13)
C5	0.0321 (12)	0.0417 (13)	0.0284 (12)	0.0061 (11)	−0.0033 (10)	0.0038 (10)
C6	0.0302 (11)	0.0349 (12)	0.0313 (12)	0.0009 (10)	0.0012 (10)	0.0064 (10)
C7	0.0395 (13)	0.0267 (11)	0.0285 (11)	0.0020 (11)	0.0000 (10)	−0.0033 (9)
C8	0.0464 (14)	0.0357 (13)	0.0349 (13)	0.0066 (12)	−0.0036 (11)	−0.0049 (11)
C9	0.0389 (13)	0.0345 (12)	0.0320 (12)	0.0016 (11)	−0.0054 (10)	0.0005 (10)
C10	0.0347 (13)	0.0382 (13)	0.0478 (16)	0.0000 (11)	−0.0086 (11)	−0.0010 (11)
C11	0.0296 (12)	0.0336 (11)	0.0447 (14)	−0.0059 (12)	0.0005 (10)	0.0007 (12)
C12	0.0402 (13)	0.0259 (11)	0.0379 (12)	−0.0034 (12)	−0.0031 (11)	0.0009 (10)
C13	0.0254 (11)	0.0278 (11)	0.0343 (12)	0.0019 (9)	−0.0019 (9)	0.0001 (9)
C14	0.0402 (15)	0.0368 (13)	0.0487 (16)	0.0092 (12)	0.0052 (12)	0.0001 (12)
C15	0.0344 (13)	0.0344 (12)	0.0335 (13)	−0.0007 (11)	0.0046 (10)	0.0006 (10)
C16	0.0343 (12)	0.0247 (11)	0.0317 (12)	−0.0020 (9)	0.0023 (10)	0.0021 (9)
C17	0.0505 (16)	0.0296 (12)	0.0462 (15)	−0.0046 (12)	−0.0026 (12)	0.0077 (11)
C18	0.0610 (17)	0.0268 (12)	0.0492 (16)	0.0005 (14)	−0.0026 (14)	−0.0014 (11)
C19	0.090 (3)	0.0321 (13)	0.0596 (19)	−0.0149 (18)	−0.0038 (18)	−0.0001 (13)
C20	0.091 (3)	0.125 (3)	0.071 (2)	0.054 (3)	−0.008 (2)	−0.043 (2)
C21	0.069 (2)	0.0529 (16)	0.0292 (13)	−0.0075 (15)	0.0065 (12)	0.0008 (12)
Cl1	0.0432 (3)	0.0490 (4)	0.0611 (4)	−0.0014 (3)	−0.0007 (3)	0.0089 (4)

Geometric parameters (Å, º) top

O1—N1	1.397 (3)	C10—H10A	0.9700
O1—C20	1.424 (4)	C10—H10B	0.9700
O2—C8	1.201 (3)	C11—C12	1.536 (3)
O3—C14	1.421 (3)	C11—C15	1.561 (3)
O3—C9	1.423 (3)	C11—H11	0.9800
N1—C8	1.369 (3)	C12—C18	1.506 (3)
N1—C5	1.410 (3)	C12—C17	1.546 (4)
N2—C21	1.493 (3)	C12—C13	1.570 (3)
N2—C16	1.506 (3)	C13—C16	1.540 (3)
N2—C17	1.513 (3)	C13—H13	0.9800
N2—H2X	0.893 (17)	C14—C15	1.509 (3)
C1—C6	1.387 (3)	C14—H14A	0.9700
C1—C2	1.386 (4)	C14—H14B	0.9700
C1—H1	0.9300	C15—C16	1.540 (3)
C2—C3	1.387 (4)	C15—H15	0.9800
C2—H2	0.9300	C16—H16	0.9800
C3—C4	1.380 (4)	C17—H17A	0.9700
C3—H3	0.9300	C17—H17B	0.9700
C4—C5	1.370 (4)	C18—C19	1.299 (4)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.396 (3)	C19—H19A	0.9300
C6—C7	1.522 (3)	C19—H19B	0.9300
C7—C13	1.552 (3)	C20—H20A	0.9599
C7—C8	1.561 (3)	C20—H20B	0.9599
C7—C9	1.566 (3)	C20—H20C	0.9599
C9—C10	1.507 (3)	C21—H21A	0.9599
C9—H9	0.9800	C21—H21B	0.9599
C10—C11	1.541 (3)	C21—H21C	0.9599

N1—O1—C20	111.2 (2)	C15—C11—H11	111.8
C14—O3—C9	114.59 (18)	C18—C12—C11	117.4 (2)
C8—N1—O1	120.2 (2)	C18—C12—C17	108.02 (19)
C8—N1—C5	113.0 (2)	C11—C12—C17	108.3 (2)
O1—N1—C5	119.3 (2)	C18—C12—C13	121.3 (2)
C21—N2—C16	116.9 (2)	C11—C12—C13	99.19 (17)
C21—N2—C17	115.8 (2)	C17—C12—C13	101.04 (19)
C16—N2—C17	103.02 (17)	C16—C13—C7	113.73 (18)
C21—N2—H2X	108.7 (16)	C16—C13—C12	93.14 (17)
C16—N2—H2X	102.7 (16)	C7—C13—C12	116.79 (18)
C17—N2—H2X	108.7 (16)	C16—C13—H13	110.7
C6—C1—C2	119.6 (2)	C7—C13—H13	110.7
C6—C1—H1	120.2	C12—C13—H13	110.7
C2—C1—H1	120.2	O3—C14—C15	112.7 (2)
C3—C2—C1	121.1 (3)	O3—C14—H14A	109.0
C3—C2—H2	119.4	C15—C14—H14A	109.0
C1—C2—H2	119.4	O3—C14—H14B	109.0
C4—C3—C2	120.4 (3)	C15—C14—H14B	109.0
C4—C3—H3	119.8	H14A—C14—H14B	107.8
C2—C3—H3	119.8	C14—C15—C16	113.1 (2)
C5—C4—C3	117.5 (3)	C14—C15—C11	112.8 (2)
C5—C4—H4	121.2	C16—C15—C11	102.83 (18)
C3—C4—H4	121.2	C14—C15—H15	109.3
C4—C5—C6	123.9 (2)	C16—C15—H15	109.3
C4—C5—N1	127.9 (2)	C11—C15—H15	109.3
C6—C5—N1	108.1 (2)	N2—C16—C15	107.54 (19)
C1—C6—C5	117.4 (2)	N2—C16—C13	99.88 (18)
C1—C6—C7	132.8 (2)	C15—C16—C13	104.50 (19)
C5—C6—C7	109.7 (2)	N2—C16—H16	114.5
C6—C7—C13	113.31 (18)	C15—C16—H16	114.5
C6—C7—C8	101.56 (19)	C13—C16—H16	114.5
C13—C7—C8	111.59 (18)	N2—C17—C12	104.57 (18)
C6—C7—C9	111.66 (18)	N2—C17—H17A	110.8
C13—C7—C9	111.36 (19)	C12—C17—H17A	110.8
C8—C7—C9	106.78 (19)	N2—C17—H17B	110.8
O2—C8—N1	124.8 (2)	C12—C17—H17B	110.8
O2—C8—C7	128.6 (2)	H17A—C17—H17B	108.9
N1—C8—C7	106.6 (2)	C19—C18—C12	125.1 (3)
O3—C9—C10	112.1 (2)	C19—C18—H18	117.4
O3—C9—C7	109.13 (19)	C12—C18—H18	117.4
C10—C9—C7	111.30 (19)	C18—C19—H19A	120.0
O3—C9—H9	108.1	C18—C19—H19B	120.0
C10—C9—H9	108.1	H19A—C19—H19B	120.0
C7—C9—H9	108.1	O1—C20—H20A	109.5
C9—C10—C11	109.0 (2)	O1—C20—H20B	109.5
C9—C10—H10A	109.9	H20A—C20—H20B	109.5
C11—C10—H10A	109.9	O1—C20—H20C	109.5
C9—C10—H10B	109.9	H20A—C20—H20C	109.5
C11—C10—H10B	109.9	H20B—C20—H20C	109.5
H10A—C10—H10B	108.3	N2—C21—H21A	109.5
C12—C11—C10	110.23 (19)	N2—C21—H21B	109.5
C12—C11—C15	102.40 (18)	H21A—C21—H21B	109.5
C10—C11—C15	108.4 (2)	N2—C21—H21C	109.5
C12—C11—H11	111.8	H21A—C21—H21C	109.5
C10—C11—H11	111.8	H21B—C21—H21C	109.5

C20—O1—N1—C8	−93.7 (3)	C10—C11—C12—C18	−63.2 (3)
C20—O1—N1—C5	118.8 (3)	C15—C11—C12—C18	−178.4 (2)
C6—C1—C2—C3	−0.4 (4)	C10—C11—C12—C17	174.27 (19)
C1—C2—C3—C4	−0.3 (4)	C15—C11—C12—C17	59.1 (2)
C2—C3—C4—C5	0.3 (4)	C10—C11—C12—C13	69.3 (2)
C3—C4—C5—C6	0.4 (4)	C15—C11—C12—C13	−45.8 (2)
C3—C4—C5—N1	−179.0 (2)	C6—C7—C13—C16	69.4 (3)
C8—N1—C5—C4	−171.1 (2)	C8—C7—C13—C16	−176.7 (2)
O1—N1—C5—C4	−21.4 (4)	C9—C7—C13—C16	−57.5 (2)
C8—N1—C5—C6	9.5 (3)	C6—C7—C13—C12	176.20 (19)
O1—N1—C5—C6	159.2 (2)	C8—C7—C13—C12	−69.9 (3)
C2—C1—C6—C5	1.1 (4)	C9—C7—C13—C12	49.3 (2)
C2—C1—C6—C7	−176.2 (2)	C18—C12—C13—C16	−170.9 (2)
C4—C5—C6—C1	−1.1 (4)	C11—C12—C13—C16	59.08 (19)
N1—C5—C6—C1	178.4 (2)	C17—C12—C13—C16	−51.7 (2)
C4—C5—C6—C7	176.8 (2)	C18—C12—C13—C7	70.5 (3)
N1—C5—C6—C7	−3.8 (3)	C11—C12—C13—C7	−59.5 (2)
C1—C6—C7—C13	−65.0 (3)	C17—C12—C13—C7	−170.33 (19)
C5—C6—C7—C13	117.5 (2)	C9—O3—C14—C15	32.0 (3)
C1—C6—C7—C8	175.2 (3)	O3—C14—C15—C16	57.9 (3)
C5—C6—C7—C8	−2.3 (2)	O3—C14—C15—C11	−58.3 (3)
C1—C6—C7—C9	61.7 (3)	C12—C11—C15—C14	135.3 (2)
C5—C6—C7—C9	−115.7 (2)	C10—C11—C15—C14	18.9 (3)
O1—N1—C8—O2	17.6 (4)	C12—C11—C15—C16	13.1 (2)
C5—N1—C8—O2	166.9 (2)	C10—C11—C15—C16	−103.3 (2)
O1—N1—C8—C7	−160.2 (2)	C21—N2—C16—C15	−64.7 (3)
C5—N1—C8—C7	−10.8 (3)	C17—N2—C16—C15	63.4 (2)
C6—C7—C8—O2	−170.0 (3)	C21—N2—C16—C13	−173.5 (2)
C13—C7—C8—O2	69.0 (3)	C17—N2—C16—C13	−45.3 (2)
C9—C7—C8—O2	−52.9 (3)	C14—C15—C16—N2	157.6 (2)
C6—C7—C8—N1	7.6 (2)	C11—C15—C16—N2	−80.4 (2)
C13—C7—C8—N1	−113.4 (2)	C14—C15—C16—C13	−96.9 (2)
C9—C7—C8—N1	124.7 (2)	C11—C15—C16—C13	25.1 (2)
C14—O3—C9—C10	29.8 (3)	C7—C13—C16—N2	−179.29 (18)
C14—O3—C9—C7	−94.0 (2)	C12—C13—C16—N2	59.58 (19)
C6—C7—C9—O3	−47.0 (2)	C7—C13—C16—C15	69.6 (2)
C13—C7—C9—O3	80.8 (2)	C12—C13—C16—C15	−51.6 (2)
C8—C7—C9—O3	−157.18 (19)	C21—N2—C17—C12	139.9 (2)
C6—C7—C9—C10	−171.23 (19)	C16—N2—C17—C12	11.0 (3)
C13—C7—C9—C10	−43.5 (2)	C18—C12—C17—N2	154.7 (2)
C8—C7—C9—C10	78.6 (2)	C11—C12—C17—N2	−77.3 (2)
O3—C9—C10—C11	−68.2 (3)	C13—C12—C17—N2	26.3 (2)
C7—C9—C10—C11	54.3 (3)	C11—C12—C18—C19	−26.7 (4)
C9—C10—C11—C12	−72.5 (2)	C17—C12—C18—C19	95.9 (3)
C9—C10—C11—C15	38.8 (2)	C13—C12—C18—C19	−148.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O2	0.97	2.51	3.131 (4)	122
C11—H11···Cl1	0.98	2.92	3.662 (3)	133
C15—H15···Cl1	0.98	2.86	3.628 (3)	136
C20—H20C···O2	0.96	2.86	3.323 (5)	111
N2—H2X···Cl1ⁱ	0.89 (2)	2.14 (2)	3.007 (3)	163 (2)
C4—H4···O1ⁱⁱ	0.93	2.86	3.434 (3)	121
C16—H16···Cl1ⁱⁱⁱ	0.98	2.85	3.623 (3)	136
C21—H21B···Cl1ⁱⁱⁱ	0.96	2.86	3.741 (3)	153
C19—H19B···O3^iv	0.93	2.57	3.399 (3)	149
C20—H20B···O2^v	0.96	2.66	3.264 (4)	122

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+3/2, −z; (iii) −x+1, y+1/2, −z+1/2; (iv) x, y−1, z; (v) x+1/2, −y+1/2, −z.

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Gelsevirine hydro­chloride

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Gelsevirine hydrochloride