Psilacetin derivatives: fumarate salts of the meth­yl–ethyl, meth­yl–allyl and diallyl variants of the psilocin prodrug

Pham, D.N.K.; Chadeayne, A.R.; Golen, J.A.; Manke, D.R.

doi:10.1107/S2056989021000116

Psilacetin derivatives: fumarate salts of the methyl–ethyl, methyl–allyl and diallyl variants of the psilocin prodrug

D. N. K. Pham, A. R. Chadeayne, J. A. Golen and D. R. Manke

The crystal structures of the fumarate salts of three prodrugs of synthetic psychedelics (4-AcO-MET, 4-AcO-MALT and 4-AcO-DALT) are reported.

Keywords: crystal structure; tryptamines; indoles; fumarates; hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021000116/hb7959sup1.cif Contains datablocks I, II, III, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989021000116/hb7959Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021000116/hb7959Isup5.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989021000116/hb7959IIsup3.hkl Contains datablock II
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021000116/hb7959IIsup6.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989021000116/hb7959IIIsup4.hkl Contains datablock III
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021000116/hb7959IIIsup7.cml Supplementary material

CCDC references: 2053845; 2053844; 2053843

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R factor = 0.052
wR factor = 0.146
Data-to-parameter ratio = 13.0

Structure: II

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.005 Å
R factor = 0.043
wR factor = 0.113
Data-to-parameter ratio = 14.4

Structure: III

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R factor = 0.051
wR factor = 0.140
Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level A
PLAT413_ALERT_2_A Short Inter XH3 .. XHn     H1C      ..H14E     .       1.19 Ang.
                                              1-x,1/2+y,1-z  =      2_656 Check
PLAT413_ALERT_2_A Short Inter XH3 .. XHn     H4       ..H14D     .       1.67 Ang.
                                              2-x,1/2+y,1-z  =      2_756 Check
PLAT413_ALERT_2_A Short Inter XH3 .. XHn     H4       ..H14F     .       1.66 Ang.
                                              2-x,1/2+y,1-z  =      2_756 Check

Alert level C
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -0.300
           From the CIF: _refine_ls_abs_structure_Flack_su    0.300
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       6.83 Note
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        C16 Check
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.6 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00638 Ang.
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H1B      ..H14E     .       2.06 Ang.
                                              1-x,1/2+y,1-z  =      2_656 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         19 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         12 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         17 Note
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.300 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          2 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          4 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    N2       --C15      .        5.7 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        26% Note
PLAT432_ALERT_2_G Short Inter X...Y Contact  C1       ..C14A             2.86 Ang.
                                              1-x,1/2+y,1-z  =      2_656 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  C4       ..C14A             2.67 Ang.
                                              2-x,1/2+y,1-z  =      2_756 Check
PLAT791_ALERT_4_G Model has Chirality at N2          (Sohnke SpGr)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         15 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   3 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   8 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  13 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: II


Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.400
           From the CIF: _refine_ls_abs_structure_Flack_su    0.300
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        C17 Check
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.7 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00525 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         28 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         24 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          6 Note
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.300 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT791_ALERT_4_G Model has Chirality at N2          (Sohnke SpGr)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          4 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by .       0.26 Check
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: III



Alert level C
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.3 Note
PLAT414_ALERT_2_C Short Intra D-H..H-X       H2       ..H13A             1.97 Ang.
                                                      x,y,z  =      1_555 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.724 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         25 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         19 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         26 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          8 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...       2.00 Check
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          2 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         10 Report
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          2 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          2 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          2 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C13      --C14      .       15.5 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        27% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )        75% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          4 Note
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        114 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  19 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Computing details top

For all structures, data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

[2-(4-Acetyloxy-1H-indol-3-yl)ethyl](methyl)ethylazanium 3-carboxyprop-2-enoate (I) top

Crystal data top

C₁₅H₂₁N₂O₂⁺·C₄H₃O₄⁻	F(000) = 400
M_r = 376.40	D_x = 1.279 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.9555 (4) Å	Cell parameters from 9372 reflections
b = 13.3696 (7) Å	θ = 2.7–25.4°
c = 9.9708 (5) Å	µ = 0.10 mm⁻¹
β = 112.874 (2)°	T = 200 K
V = 977.12 (9) Å³	Block, colorless
Z = 2	0.24 × 0.2 × 0.2 mm

Data collection top

Bruker D8 Venture CMOS diffractometer	3232 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.036
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θ_max = 25.4°, θ_min = 2.8°
T_min = 0.708, T_max = 0.745	h = −9→9
21973 measured reflections	k = −16→16
3536 independent reflections	l = −11→12

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.052	w = 1/[σ²(F_o²) + (0.0859P)² + 0.4056P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.146	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.39 e Å⁻³
3536 reflections	Δρ_min = −0.55 e Å⁻³
271 parameters	Absolute structure: Flack x determined using 1411 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
15 restraints	Absolute structure parameter: −0.3 (3)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.8969 (4)	0.6685 (2)	0.3476 (3)	0.0419 (7)
O2	0.6590 (4)	0.7649 (2)	0.2143 (3)	0.0527 (8)
O3	0.6091 (4)	0.4634 (4)	0.5977 (3)	0.0643 (11)
O4	0.3948 (4)	0.4494 (4)	0.3791 (3)	0.0726 (12)
O5	−0.1636 (4)	0.4458 (3)	0.4883 (3)	0.0464 (7)
H5A	−0.228 (7)	0.461 (5)	0.541 (5)	0.070*
O6	0.0341 (4)	0.5232 (3)	0.6851 (3)	0.0530 (8)
N1	0.8829 (5)	0.5556 (3)	−0.1012 (4)	0.0445 (8)
H1	0.909 (7)	0.546 (4)	−0.177 (3)	0.053*
C1	0.6770 (8)	0.7029 (4)	0.4462 (5)	0.0609 (13)
H1A	0.771261	0.727703	0.536780	0.091*
H1B	0.656163	0.631605	0.456386	0.091*
H1C	0.563452	0.739969	0.425935	0.091*
C2	0.7388 (6)	0.7176 (3)	0.3229 (4)	0.0398 (9)
C3	0.9685 (5)	0.6723 (3)	0.2378 (4)	0.0377 (9)
C4	1.1178 (6)	0.7317 (3)	0.2611 (5)	0.0505 (11)
H4	1.165836	0.772222	0.345887	0.061*
C5	1.1983 (7)	0.7322 (4)	0.1596 (6)	0.0581 (13)
H5	1.303718	0.772121	0.177668	0.070*
C6	1.1292 (7)	0.6765 (4)	0.0340 (6)	0.0547 (12)
H6	1.183090	0.678752	−0.035920	0.066*
C7	0.9784 (6)	0.6171 (3)	0.0127 (5)	0.0399 (9)
C8	0.8952 (5)	0.6117 (3)	0.1155 (4)	0.0344 (8)
C9	0.7462 (5)	0.5416 (3)	0.0580 (4)	0.0347 (8)
C10	0.7465 (6)	0.5098 (3)	−0.0720 (4)	0.0413 (9)
H10	0.663545	0.462369	−0.133842	0.050*
C11	0.6170 (6)	0.5075 (3)	0.1251 (5)	0.0462 (10)
H11A	0.500209	0.544176	0.080710	0.055*	0.760 (7)
H11B	0.669365	0.522179	0.230754	0.055*	0.760 (7)
H11C	0.493724	0.534844	0.069534	0.055*	0.240 (7)
H11D	0.658515	0.532211	0.226482	0.055*	0.240 (7)
N2	0.4319 (8)	0.3670 (4)	0.1512 (6)	0.0478 (14)	0.760 (7)
H2	0.460 (10)	0.389 (6)	0.240 (4)	0.057*	0.760 (7)
C12	0.583 (2)	0.3971 (6)	0.1019 (15)	0.0747 (14)	0.760 (7)
H12A	0.695565	0.359695	0.158198	0.090*	0.760 (7)
H12B	0.546626	0.380879	−0.002452	0.090*	0.760 (7)
C13	0.4415 (12)	0.2578 (5)	0.1741 (9)	0.0747 (14)	0.760 (7)
H13A	0.434068	0.222514	0.084645	0.090*	0.760 (7)
H13B	0.339870	0.234739	0.200220	0.090*	0.760 (7)
C14	0.6257 (12)	0.2371 (6)	0.2991 (9)	0.0747 (14)	0.760 (7)
H14A	0.609720	0.186452	0.364171	0.112*	0.760 (7)
H14B	0.671948	0.299017	0.353700	0.112*	0.760 (7)
H14C	0.712937	0.212798	0.259233	0.112*	0.760 (7)
C15	0.2372 (8)	0.3878 (5)	0.0459 (7)	0.0518 (14)	0.760 (7)
H15A	0.222136	0.459583	0.024871	0.078*	0.760 (7)
H15B	0.152161	0.366435	0.089854	0.078*	0.760 (7)
H15C	0.211710	0.350719	−0.044649	0.078*	0.760 (7)
N2A	0.5331 (17)	0.3315 (9)	0.2166 (13)	0.024 (3)	0.240 (7)
H2A	0.51 (2)	0.371 (11)	0.278 (13)	0.029*	0.240 (7)
C12A	0.609 (7)	0.3915 (11)	0.124 (5)	0.0747 (14)	0.240 (7)
H12C	0.539526	0.371383	0.021726	0.090*	0.240 (7)
H12D	0.736058	0.367924	0.149239	0.090*	0.240 (7)
C13A	0.555 (4)	0.2363 (15)	0.305 (2)	0.0747 (14)	0.240 (7)
H13C	0.640638	0.192254	0.282152	0.090*	0.240 (7)
H13D	0.435712	0.202054	0.269481	0.090*	0.240 (7)
C14A	0.623 (4)	0.242 (2)	0.471 (2)	0.0747 (14)	0.240 (7)
H14D	0.724365	0.195394	0.515462	0.112*	0.240 (7)
H14E	0.523313	0.224946	0.501539	0.112*	0.240 (7)
H14F	0.664930	0.310475	0.503391	0.112*	0.240 (7)
C15A	0.335 (2)	0.3065 (18)	0.116 (2)	0.0518 (14)	0.240 (7)
H15D	0.277454	0.268541	0.170713	0.078*	0.240 (7)
H15E	0.334919	0.266491	0.033717	0.078*	0.240 (7)
H15F	0.267400	0.368689	0.079997	0.078*	0.240 (7)
C16	0.4441 (5)	0.4620 (3)	0.5089 (4)	0.0363 (8)
C17	0.3065 (5)	0.4772 (3)	0.5751 (4)	0.0384 (9)
H17	0.348389	0.491198	0.676267	0.046*
C18	0.1302 (5)	0.4720 (3)	0.4987 (4)	0.0375 (8)
H18	0.087892	0.460653	0.396827	0.045*
C19	−0.0063 (5)	0.4833 (3)	0.5668 (4)	0.0366 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0513 (17)	0.0443 (15)	0.0315 (13)	0.0013 (13)	0.0174 (12)	−0.0005 (12)
O2	0.0541 (18)	0.060 (2)	0.0505 (18)	0.0116 (16)	0.0277 (15)	0.0128 (16)
O3	0.0266 (14)	0.130 (3)	0.0416 (16)	0.0008 (18)	0.0187 (12)	−0.0061 (19)
O4	0.0403 (16)	0.144 (4)	0.0440 (18)	0.002 (2)	0.0277 (14)	−0.027 (2)
O5	0.0324 (14)	0.069 (2)	0.0456 (16)	−0.0014 (13)	0.0234 (12)	−0.0050 (14)
O6	0.0393 (15)	0.087 (2)	0.0433 (16)	−0.0022 (15)	0.0274 (13)	−0.0111 (16)
N1	0.057 (2)	0.051 (2)	0.0400 (18)	0.0093 (17)	0.0352 (17)	0.0022 (15)
C1	0.089 (4)	0.057 (3)	0.059 (3)	0.012 (3)	0.054 (3)	0.006 (2)
C2	0.052 (2)	0.036 (2)	0.039 (2)	−0.0023 (17)	0.0260 (18)	−0.0033 (17)
C3	0.038 (2)	0.0386 (19)	0.039 (2)	0.0028 (16)	0.0168 (17)	0.0023 (16)
C4	0.043 (2)	0.051 (3)	0.051 (2)	−0.0071 (19)	0.0112 (19)	0.000 (2)
C5	0.043 (2)	0.063 (3)	0.073 (3)	−0.009 (2)	0.028 (2)	0.005 (3)
C6	0.049 (3)	0.056 (3)	0.077 (3)	0.003 (2)	0.045 (2)	0.012 (2)
C7	0.040 (2)	0.042 (2)	0.046 (2)	0.0097 (17)	0.0263 (18)	0.0063 (17)
C8	0.0338 (19)	0.0388 (19)	0.0367 (19)	0.0029 (15)	0.0201 (16)	0.0036 (15)
C9	0.0394 (19)	0.0374 (19)	0.0324 (18)	0.0029 (15)	0.0194 (16)	−0.0015 (15)
C10	0.045 (2)	0.047 (2)	0.0367 (19)	0.0011 (18)	0.0205 (17)	−0.0045 (17)
C11	0.052 (2)	0.053 (2)	0.048 (2)	−0.0120 (19)	0.035 (2)	−0.0122 (19)
N2	0.055 (3)	0.046 (3)	0.054 (3)	−0.016 (3)	0.034 (3)	−0.018 (3)
C12	0.100 (4)	0.061 (2)	0.084 (3)	−0.020 (2)	0.060 (3)	−0.009 (2)
C13	0.100 (4)	0.061 (2)	0.084 (3)	−0.020 (2)	0.060 (3)	−0.009 (2)
C14	0.100 (4)	0.061 (2)	0.084 (3)	−0.020 (2)	0.060 (3)	−0.009 (2)
C15	0.043 (3)	0.064 (4)	0.046 (3)	0.000 (3)	0.014 (2)	−0.016 (3)
N2A	0.024 (6)	0.025 (6)	0.021 (6)	−0.009 (5)	0.007 (5)	0.004 (5)
C12A	0.100 (4)	0.061 (2)	0.084 (3)	−0.020 (2)	0.060 (3)	−0.009 (2)
C13A	0.100 (4)	0.061 (2)	0.084 (3)	−0.020 (2)	0.060 (3)	−0.009 (2)
C14A	0.100 (4)	0.061 (2)	0.084 (3)	−0.020 (2)	0.060 (3)	−0.009 (2)
C15A	0.043 (3)	0.064 (4)	0.046 (3)	0.000 (3)	0.014 (2)	−0.016 (3)
C16	0.0355 (18)	0.045 (2)	0.0360 (19)	−0.0002 (17)	0.0220 (15)	−0.0020 (16)
C17	0.0327 (18)	0.056 (2)	0.0319 (17)	0.0024 (17)	0.0184 (15)	0.0001 (17)
C18	0.0340 (18)	0.051 (2)	0.0343 (18)	0.0040 (17)	0.0209 (15)	0.0009 (17)
C19	0.0316 (18)	0.048 (2)	0.0373 (19)	0.0052 (16)	0.0209 (15)	0.0039 (17)

Geometric parameters (Å, º) top

O1—C2	1.354 (5)	N2—C12	1.517 (10)
O1—C3	1.418 (5)	N2—C13	1.476 (8)
O2—C2	1.200 (5)	N2—C15	1.521 (8)
O3—C16	1.267 (5)	C12—H12A	0.9900
O4—C16	1.209 (5)	C12—H12B	0.9900
O5—H5A	0.886 (15)	C13—H13A	0.9900
O5—C19	1.292 (5)	C13—H13B	0.9900
O6—C19	1.218 (5)	C13—C14	1.535 (10)
N1—H1	0.862 (14)	C14—H14A	0.9800
N1—C7	1.368 (6)	C14—H14B	0.9800
N1—C10	1.372 (6)	C14—H14C	0.9800
C1—H1A	0.9800	C15—H15A	0.9800
C1—H1B	0.9800	C15—H15B	0.9800
C1—H1C	0.9800	C15—H15C	0.9800
C1—C2	1.504 (6)	N2A—H2A	0.870 (15)
C3—C4	1.371 (6)	N2A—C12A	1.518 (14)
C3—C8	1.390 (6)	N2A—C13A	1.521 (13)
C4—H4	0.9500	N2A—C15A	1.538 (12)
C4—C5	1.392 (7)	C12A—H12C	0.9900
C5—H5	0.9500	C12A—H12D	0.9900
C5—C6	1.376 (8)	C13A—H13C	0.9900
C6—H6	0.9500	C13A—H13D	0.9900
C6—C7	1.385 (7)	C13A—C14A	1.532 (14)
C7—C8	1.422 (5)	C14A—H14D	0.9800
C8—C9	1.443 (6)	C14A—H14E	0.9800
C9—C10	1.365 (5)	C14A—H14F	0.9800
C9—C11	1.500 (5)	C15A—H15D	0.9800
C10—H10	0.9500	C15A—H15E	0.9800
C11—H11A	0.9900	C15A—H15F	0.9800
C11—H11B	0.9900	C16—C17	1.495 (5)
C11—H11C	0.9900	C17—H17	0.9500
C11—H11D	0.9900	C17—C18	1.312 (5)
C11—C12	1.501 (9)	C18—H18	0.9500
C11—C12A	1.551 (14)	C18—C19	1.496 (5)
N2—H2	0.875 (15)

C2—O1—C3	117.8 (3)	H12A—C12—H12B	108.3
C19—O5—H5A	101 (4)	N2—C13—H13A	110.5
C7—N1—H1	125 (3)	N2—C13—H13B	110.5
C7—N1—C10	108.7 (3)	N2—C13—C14	106.2 (6)
C10—N1—H1	126 (3)	H13A—C13—H13B	108.7
H1A—C1—H1B	109.5	C14—C13—H13A	110.5
H1A—C1—H1C	109.5	C14—C13—H13B	110.5
H1B—C1—H1C	109.5	C13—C14—H14A	109.5
C2—C1—H1A	109.5	C13—C14—H14B	109.5
C2—C1—H1B	109.5	C13—C14—H14C	109.5
C2—C1—H1C	109.5	H14A—C14—H14B	109.5
O1—C2—C1	111.3 (4)	H14A—C14—H14C	109.5
O2—C2—O1	123.2 (4)	H14B—C14—H14C	109.5
O2—C2—C1	125.4 (4)	N2—C15—H15A	109.5
C4—C3—O1	118.1 (4)	N2—C15—H15B	109.5
C4—C3—C8	121.8 (4)	N2—C15—H15C	109.5
C8—C3—O1	119.9 (3)	H15A—C15—H15B	109.5
C3—C4—H4	120.2	H15A—C15—H15C	109.5
C3—C4—C5	119.5 (4)	H15B—C15—H15C	109.5
C5—C4—H4	120.2	C12A—N2A—H2A	109 (10)
C4—C5—H5	119.2	C12A—N2A—C13A	144 (2)
C6—C5—C4	121.7 (4)	C12A—N2A—C15A	106 (2)
C6—C5—H5	119.2	C13A—N2A—H2A	97 (10)
C5—C6—H6	121.1	C13A—N2A—C15A	93.2 (16)
C5—C6—C7	117.8 (4)	C15A—N2A—H2A	101 (10)
C7—C6—H6	121.1	C11—C12A—H12C	106.5
N1—C7—C6	129.8 (4)	C11—C12A—H12D	106.5
N1—C7—C8	107.7 (3)	N2A—C12A—C11	123.2 (16)
C6—C7—C8	122.5 (4)	N2A—C12A—H12C	106.5
C3—C8—C7	116.7 (4)	N2A—C12A—H12D	106.5
C3—C8—C9	136.6 (4)	H12C—C12A—H12D	106.5
C7—C8—C9	106.7 (3)	N2A—C13A—H13C	107.4
C8—C9—C11	128.3 (3)	N2A—C13A—H13D	107.4
C10—C9—C8	105.9 (3)	N2A—C13A—C14A	119.8 (18)
C10—C9—C11	125.7 (4)	H13C—C13A—H13D	106.9
N1—C10—H10	124.6	C14A—C13A—H13C	107.4
C9—C10—N1	110.9 (4)	C14A—C13A—H13D	107.4
C9—C10—H10	124.6	C13A—C14A—H14D	109.5
C9—C11—H11A	109.6	C13A—C14A—H14E	109.5
C9—C11—H11B	109.6	C13A—C14A—H14F	109.5
C9—C11—H11C	109.8	H14D—C14A—H14E	109.5
C9—C11—H11D	109.8	H14D—C14A—H14F	109.5
C9—C11—C12	110.2 (5)	H14E—C14A—H14F	109.5
C9—C11—C12A	109.4 (10)	N2A—C15A—H15D	109.5
H11A—C11—H11B	108.1	N2A—C15A—H15E	109.5
H11C—C11—H11D	108.2	N2A—C15A—H15F	109.5
C12—C11—H11A	109.6	H15D—C15A—H15E	109.5
C12—C11—H11B	109.6	H15D—C15A—H15F	109.5
C12A—C11—H11C	109.8	H15E—C15A—H15F	109.5
C12A—C11—H11D	109.8	O3—C16—C17	115.3 (3)
C12—N2—H2	108 (6)	O4—C16—O3	124.5 (3)
C12—N2—C15	116.7 (8)	O4—C16—C17	120.2 (3)
C13—N2—H2	101 (6)	C16—C17—H17	118.7
C13—N2—C12	108.3 (6)	C18—C17—C16	122.5 (3)
C13—N2—C15	105.4 (5)	C18—C17—H17	118.7
C15—N2—H2	115 (5)	C17—C18—H18	118.9
C11—C12—N2	109.3 (6)	C17—C18—C19	122.2 (3)
C11—C12—H12A	109.8	C19—C18—H18	118.9
C11—C12—H12B	109.8	O5—C19—C18	112.9 (3)
N2—C12—H12A	109.8	O6—C19—O5	125.9 (3)
N2—C12—H12B	109.8	O6—C19—C18	121.2 (3)

O1—C3—C4—C5	176.0 (4)	C7—C8—C9—C11	178.7 (4)
O1—C3—C8—C7	−177.9 (3)	C8—C3—C4—C5	0.4 (6)
O1—C3—C8—C9	3.9 (7)	C8—C9—C10—N1	−0.8 (5)
O3—C16—C17—C18	−175.9 (4)	C8—C9—C11—C12	−139.1 (7)
O4—C16—C17—C18	3.9 (7)	C8—C9—C11—C12A	−129 (2)
N1—C7—C8—C3	−177.6 (3)	C9—C11—C12—N2	−172.0 (7)
N1—C7—C8—C9	1.1 (4)	C9—C11—C12A—N2A	164 (3)
C2—O1—C3—C4	105.8 (4)	C10—N1—C7—C6	178.4 (4)
C2—O1—C3—C8	−78.5 (5)	C10—N1—C7—C8	−1.6 (5)
C3—O1—C2—O2	−1.2 (6)	C10—C9—C11—C12	39.6 (9)
C3—O1—C2—C1	177.7 (4)	C10—C9—C11—C12A	49 (2)
C3—C4—C5—C6	1.8 (7)	C11—C9—C10—N1	−179.8 (4)
C3—C8—C9—C10	178.2 (5)	C12—N2—C13—C14	63.8 (9)
C3—C8—C9—C11	−2.9 (7)	C13—N2—C12—C11	−161.4 (8)
C4—C3—C8—C7	−2.3 (6)	C15—N2—C12—C11	80.0 (10)
C4—C3—C8—C9	179.4 (4)	C15—N2—C13—C14	−170.6 (5)
C4—C5—C6—C7	−1.7 (8)	C12A—N2A—C13A—C14A	110 (4)
C5—C6—C7—N1	179.6 (4)	C13A—N2A—C12A—C11	−144 (3)
C5—C6—C7—C8	−0.4 (7)	C15A—N2A—C12A—C11	97 (4)
C6—C7—C8—C3	2.4 (6)	C15A—N2A—C13A—C14A	−128 (2)
C6—C7—C8—C9	−178.9 (4)	C16—C17—C18—C19	177.5 (4)
C7—N1—C10—C9	1.6 (5)	C17—C18—C19—O5	−159.5 (4)
C7—C8—C9—C10	−0.2 (4)	C17—C18—C19—O6	19.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6ⁱ	0.86 (1)	2.02 (2)	2.858 (4)	165 (5)
N2—H2···O4	0.88 (2)	1.85 (4)	2.644 (6)	150 (7)
N2A—H2A···O4	0.87 (2)	1.94 (6)	2.776 (14)	162 (17)
O5—H5A···O3ⁱⁱ	0.89 (2)	1.61 (2)	2.459 (4)	160 (6)

Symmetry codes: (i) x+1, y, z−1; (ii) x−1, y, z.

[2-(4-Acetyloxy-1H-indol-3-yl)ethyl](methyl)prop-2-enylazanium 3-carboxyprop-2-enoate (II) top

Crystal data top

C₁₆H₂₁N₂O₂⁺·C₄H₃O₄⁻	F(000) = 412
M_r = 388.41	D_x = 1.269 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.9702 (4) Å	Cell parameters from 9882 reflections
b = 14.1788 (7) Å	θ = 2.7–25.6°
c = 9.8035 (5) Å	µ = 0.09 mm⁻¹
β = 113.394 (2)°	T = 297 K
V = 1016.80 (9) Å³	BLOCK, colourless
Z = 2	0.34 × 0.24 × 0.2 mm

Data collection top

Bruker D8 Venture CMOS diffractometer	3516 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.039
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θ_max = 25.7°, θ_min = 2.8°
T_min = 0.686, T_max = 0.745	h = −9→9
26393 measured reflections	k = −17→17
3797 independent reflections	l = −11→11

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.043	w = 1/[σ²(F_o²) + (0.0592P)² + 0.2448P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.113	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.27 e Å⁻³
3797 reflections	Δρ_min = −0.16 e Å⁻³
264 parameters	Absolute structure: Flack x determined using 1577 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
4 restraints	Absolute structure parameter: 0.4 (3)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.0798 (3)	0.7896 (2)	0.2116 (3)	0.0688 (8)
O2	−0.0241 (3)	0.69624 (16)	0.3445 (2)	0.0496 (5)
O3	0.5149 (3)	0.4747 (3)	0.3619 (3)	0.0834 (11)
O4	0.5188 (3)	0.4841 (3)	0.5856 (3)	0.0701 (8)
H4A	0.397 (2)	0.484 (4)	0.543 (5)	0.105*
O5	1.1781 (3)	0.53485 (19)	0.6822 (2)	0.0559 (6)
O6	1.1837 (2)	0.47635 (18)	0.4735 (2)	0.0493 (5)
N1	−0.4734 (4)	0.5921 (2)	−0.1031 (3)	0.0585 (8)
H1	−0.577 (3)	0.580 (3)	−0.176 (3)	0.070*
N2	0.2259 (4)	0.4086 (2)	0.1361 (3)	0.0499 (6)
H2	0.297 (4)	0.436 (3)	0.221 (3)	0.060*
C1	0.2902 (5)	0.7280 (3)	0.4444 (5)	0.0754 (12)
H1A	0.377223	0.771990	0.436158	0.113*
H1B	0.330726	0.664822	0.439678	0.113*
H1C	0.279217	0.737271	0.537570	0.113*
C2	0.1079 (5)	0.7436 (2)	0.3193 (4)	0.0506 (8)
C3	−0.2038 (4)	0.7039 (2)	0.2363 (3)	0.0464 (7)
C4	−0.3218 (6)	0.7650 (3)	0.2617 (5)	0.0642 (9)
H4	−0.281087	0.803090	0.345811	0.077*
C5	−0.5046 (6)	0.7694 (3)	0.1595 (6)	0.0776 (12)
H5	−0.584090	0.810842	0.177293	0.093*
C6	−0.5689 (5)	0.7147 (3)	0.0352 (5)	0.0685 (11)
H6	−0.690394	0.718337	−0.031497	0.082*
C7	−0.4473 (4)	0.6531 (2)	0.0109 (4)	0.0494 (8)
C8	−0.2618 (4)	0.6455 (2)	0.1114 (3)	0.0401 (6)
C9	−0.1793 (4)	0.5762 (2)	0.0515 (3)	0.0418 (6)
C10	−0.3140 (5)	0.5459 (3)	−0.0778 (3)	0.0531 (8)
H10	−0.299037	0.500150	−0.139982	0.064*
C11	0.0171 (4)	0.5439 (2)	0.1121 (4)	0.0491 (7)
H11A	0.082400	0.578146	0.062769	0.059*
H11B	0.074142	0.558138	0.217389	0.059*
C12	0.0315 (4)	0.4409 (2)	0.0897 (4)	0.0554 (8)
H12A	−0.036085	0.425881	−0.014403	0.066*
H12B	−0.024264	0.406630	0.146635	0.066*
C13	0.2451 (6)	0.3047 (3)	0.1669 (5)	0.0656 (10)
H13A	0.165728	0.271014	0.078805	0.079*
H13B	0.369974	0.285978	0.188000	0.079*
C14	0.1994 (6)	0.2777 (3)	0.2918 (5)	0.0745 (11)
H14	0.260747	0.308976	0.381312	0.089*
C15	0.0818 (9)	0.2144 (4)	0.2897 (8)	0.1105 (19)
H15A	0.017104	0.181308	0.202624	0.133*
H15B	0.061757	0.201983	0.375131	0.133*
C16	0.3019 (6)	0.4354 (4)	0.0257 (4)	0.0741 (12)
H16A	0.425726	0.413518	0.058781	0.111*
H16B	0.299241	0.502755	0.015387	0.111*
H16C	0.229752	0.407199	−0.068548	0.111*
C17	0.5946 (3)	0.4843 (2)	0.4951 (3)	0.0412 (6)
C18	0.7971 (3)	0.4950 (2)	0.5624 (3)	0.0418 (6)
H18	0.853754	0.504450	0.664454	0.050*
C19	0.8996 (3)	0.4919 (2)	0.4870 (3)	0.0406 (6)
H19	0.844150	0.482380	0.384840	0.049*
C20	1.1021 (3)	0.5030 (2)	0.5574 (3)	0.0372 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0517 (14)	0.0828 (19)	0.0643 (16)	−0.0064 (13)	0.0149 (12)	0.0250 (14)
O2	0.0521 (12)	0.0543 (12)	0.0358 (10)	−0.0098 (10)	0.0102 (9)	−0.0002 (9)
O3	0.0276 (10)	0.176 (3)	0.0441 (13)	−0.0232 (16)	0.0119 (9)	−0.0257 (17)
O4	0.0255 (10)	0.142 (3)	0.0462 (12)	−0.0035 (14)	0.0177 (9)	−0.0141 (15)
O5	0.0243 (9)	0.0955 (18)	0.0443 (12)	−0.0058 (10)	0.0098 (9)	−0.0179 (11)
O6	0.0274 (9)	0.0772 (15)	0.0464 (11)	−0.0007 (10)	0.0177 (8)	−0.0114 (10)
N1	0.0341 (14)	0.076 (2)	0.0502 (15)	−0.0136 (13)	0.0009 (12)	0.0058 (14)
N2	0.0438 (14)	0.0591 (16)	0.0439 (14)	−0.0010 (12)	0.0144 (11)	−0.0097 (12)
C1	0.053 (2)	0.077 (3)	0.071 (2)	−0.0121 (19)	−0.0019 (18)	0.006 (2)
C2	0.0490 (17)	0.0470 (17)	0.0483 (18)	−0.0062 (14)	0.0113 (14)	−0.0035 (14)
C3	0.0439 (16)	0.0499 (17)	0.0452 (16)	−0.0041 (13)	0.0176 (13)	0.0034 (14)
C4	0.071 (2)	0.063 (2)	0.069 (2)	0.0029 (18)	0.039 (2)	−0.0023 (18)
C5	0.064 (2)	0.076 (3)	0.110 (4)	0.019 (2)	0.052 (3)	0.016 (3)
C6	0.0366 (17)	0.080 (3)	0.089 (3)	0.0054 (17)	0.0247 (18)	0.019 (2)
C7	0.0334 (14)	0.0576 (18)	0.0536 (18)	−0.0082 (13)	0.0134 (13)	0.0112 (15)
C8	0.0327 (13)	0.0462 (15)	0.0385 (14)	−0.0042 (11)	0.0110 (11)	0.0070 (12)
C9	0.0397 (14)	0.0479 (15)	0.0325 (13)	−0.0044 (12)	0.0087 (11)	0.0030 (12)
C10	0.0490 (17)	0.064 (2)	0.0374 (15)	−0.0099 (16)	0.0078 (13)	−0.0025 (14)
C11	0.0408 (15)	0.0561 (18)	0.0430 (15)	0.0002 (14)	0.0087 (13)	−0.0020 (14)
C12	0.0429 (17)	0.0551 (19)	0.063 (2)	−0.0037 (14)	0.0151 (16)	−0.0039 (15)
C13	0.062 (2)	0.062 (2)	0.065 (2)	0.0093 (17)	0.0170 (18)	−0.0060 (17)
C14	0.089 (3)	0.056 (2)	0.078 (3)	0.006 (2)	0.033 (2)	0.003 (2)
C15	0.117 (5)	0.094 (4)	0.118 (4)	−0.012 (3)	0.044 (4)	0.018 (4)
C16	0.071 (2)	0.105 (3)	0.058 (2)	−0.005 (2)	0.039 (2)	−0.006 (2)
C17	0.0252 (12)	0.0562 (17)	0.0398 (15)	−0.0030 (13)	0.0104 (11)	−0.0064 (13)
C18	0.0264 (12)	0.0607 (18)	0.0370 (14)	−0.0035 (12)	0.0113 (11)	−0.0052 (13)
C19	0.0233 (12)	0.0588 (17)	0.0370 (13)	−0.0041 (12)	0.0091 (10)	−0.0037 (12)
C20	0.0232 (11)	0.0485 (15)	0.0384 (14)	−0.0016 (11)	0.0107 (10)	−0.0002 (12)

Geometric parameters (Å, º) top

O1—C2	1.185 (4)	C6—C7	1.394 (6)
O2—C2	1.351 (4)	C7—C8	1.419 (4)
O2—C3	1.408 (4)	C8—C9	1.431 (5)
O3—C17	1.212 (3)	C9—C10	1.365 (4)
O4—H4A	0.894 (14)	C9—C11	1.508 (4)
O4—C17	1.256 (3)	C10—H10	0.9300
O5—C20	1.216 (3)	C11—H11A	0.9700
O6—C20	1.290 (3)	C11—H11B	0.9700
N1—H1	0.867 (14)	C11—C12	1.488 (5)
N1—C7	1.362 (5)	C12—H12A	0.9700
N1—C10	1.362 (5)	C12—H12B	0.9700
N2—H2	0.890 (14)	C13—H13A	0.9700
N2—C12	1.502 (4)	C13—H13B	0.9700
N2—C13	1.499 (5)	C13—C14	1.460 (6)
N2—C16	1.484 (4)	C14—H14	0.9300
C1—H1A	0.9600	C14—C15	1.292 (7)
C1—H1B	0.9600	C15—H15A	0.9300
C1—H1C	0.9600	C15—H15B	0.9300
C1—C2	1.499 (5)	C16—H16A	0.9600
C3—C4	1.372 (5)	C16—H16B	0.9600
C3—C8	1.396 (4)	C16—H16C	0.9600
C4—H4	0.9300	C17—C18	1.489 (3)
C4—C5	1.404 (6)	C18—H18	0.9300
C5—H5	0.9300	C18—C19	1.302 (4)
C5—C6	1.361 (7)	C19—H19	0.9300
C6—H6	0.9300	C19—C20	1.491 (3)

C2—O2—C3	117.2 (2)	C9—C10—H10	124.7
C17—O4—H4A	114 (3)	C9—C11—H11A	109.3
C7—N1—H1	126 (3)	C9—C11—H11B	109.3
C7—N1—C10	109.2 (3)	H11A—C11—H11B	107.9
C10—N1—H1	124 (3)	C12—C11—C9	111.7 (3)
C12—N2—H2	110 (3)	C12—C11—H11A	109.3
C13—N2—H2	105 (3)	C12—C11—H11B	109.3
C13—N2—C12	111.8 (3)	N2—C12—H12A	109.1
C16—N2—H2	106 (3)	N2—C12—H12B	109.1
C16—N2—C12	111.8 (3)	C11—C12—N2	112.7 (3)
C16—N2—C13	111.1 (3)	C11—C12—H12A	109.1
H1A—C1—H1B	109.5	C11—C12—H12B	109.1
H1A—C1—H1C	109.5	H12A—C12—H12B	107.8
H1B—C1—H1C	109.5	N2—C13—H13A	109.0
C2—C1—H1A	109.5	N2—C13—H13B	109.0
C2—C1—H1B	109.5	H13A—C13—H13B	107.8
C2—C1—H1C	109.5	C14—C13—N2	112.8 (3)
O1—C2—O2	123.5 (3)	C14—C13—H13A	109.0
O1—C2—C1	126.1 (3)	C14—C13—H13B	109.0
O2—C2—C1	110.4 (3)	C13—C14—H14	116.9
C4—C3—O2	118.5 (3)	C15—C14—C13	126.1 (5)
C4—C3—C8	121.4 (3)	C15—C14—H14	116.9
C8—C3—O2	119.9 (3)	C14—C15—H15A	120.0
C3—C4—H4	120.3	C14—C15—H15B	120.0
C3—C4—C5	119.4 (4)	H15A—C15—H15B	120.0
C5—C4—H4	120.3	N2—C16—H16A	109.5
C4—C5—H5	119.0	N2—C16—H16B	109.5
C6—C5—C4	121.9 (4)	N2—C16—H16C	109.5
C6—C5—H5	119.0	H16A—C16—H16B	109.5
C5—C6—H6	121.0	H16A—C16—H16C	109.5
C5—C6—C7	118.0 (3)	H16B—C16—H16C	109.5
C7—C6—H6	121.0	O3—C17—O4	124.6 (2)
N1—C7—C6	130.4 (3)	O3—C17—C18	120.1 (2)
N1—C7—C8	107.4 (3)	O4—C17—C18	115.3 (2)
C6—C7—C8	122.2 (3)	C17—C18—H18	118.0
C3—C8—C7	117.0 (3)	C19—C18—C17	124.0 (2)
C3—C8—C9	136.1 (3)	C19—C18—H18	118.0
C7—C8—C9	106.8 (3)	C18—C19—H19	118.6
C8—C9—C11	128.4 (3)	C18—C19—C20	122.8 (2)
C10—C9—C8	106.1 (3)	C20—C19—H19	118.6
C10—C9—C11	125.5 (3)	O5—C20—O6	125.1 (2)
N1—C10—C9	110.5 (3)	O5—C20—C19	121.3 (2)
N1—C10—H10	124.7	O6—C20—C19	113.6 (2)

O2—C3—C4—C5	−176.1 (3)	C6—C7—C8—C3	−1.0 (4)
O2—C3—C8—C7	176.5 (2)	C6—C7—C8—C9	179.9 (3)
O2—C3—C8—C9	−4.7 (5)	C7—N1—C10—C9	−0.9 (4)
O3—C17—C18—C19	−2.3 (6)	C7—C8—C9—C10	−0.1 (3)
O4—C17—C18—C19	176.4 (4)	C7—C8—C9—C11	177.7 (3)
N1—C7—C8—C3	178.7 (3)	C8—C3—C4—C5	−0.4 (5)
N1—C7—C8—C9	−0.4 (3)	C8—C9—C10—N1	0.6 (4)
N2—C13—C14—C15	125.8 (5)	C8—C9—C11—C12	142.7 (3)
C2—O2—C3—C4	−100.4 (3)	C9—C11—C12—N2	174.6 (3)
C2—O2—C3—C8	83.9 (4)	C10—N1—C7—C6	−179.6 (4)
C3—O2—C2—O1	−0.7 (5)	C10—N1—C7—C8	0.8 (4)
C3—O2—C2—C1	−180.0 (3)	C10—C9—C11—C12	−39.8 (4)
C3—C4—C5—C6	−0.1 (6)	C11—C9—C10—N1	−177.3 (3)
C3—C8—C9—C10	−179.0 (3)	C12—N2—C13—C14	−63.6 (4)
C3—C8—C9—C11	−1.1 (6)	C13—N2—C12—C11	158.9 (3)
C4—C3—C8—C7	0.9 (5)	C16—N2—C12—C11	−75.8 (4)
C4—C3—C8—C9	179.7 (3)	C16—N2—C13—C14	170.7 (3)
C4—C5—C6—C7	0.0 (6)	C17—C18—C19—C20	179.9 (3)
C5—C6—C7—N1	−179.0 (4)	C18—C19—C20—O5	−15.6 (5)
C5—C6—C7—C8	0.5 (5)	C18—C19—C20—O6	164.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.87 (1)	2.00 (2)	2.857 (3)	169 (4)
O4—H4A···O6ⁱⁱ	0.89 (1)	1.56 (2)	2.454 (3)	175 (6)

Symmetry codes: (i) x−2, y, z−1; (ii) x−1, y, z.

Bis{[2-(4-acetyloxy-1H-indol-3-yl)ethyl]diprop-2-enylazanium} but-2-enedioate–(E)-butenedioic acid (1/1) (III) top

Crystal data top

2C₁₈H₂₃N₂O₂⁺·C₄H₂O₄²⁻·C₄H₄O₄	F(000) = 1760
M_r = 828.90	D_x = 1.270 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.6642 (19) Å	Cell parameters from 9906 reflections
b = 8.4204 (7) Å	θ = 2.6–24.9°
c = 23.4002 (18) Å	µ = 0.09 mm⁻¹
β = 111.614 (2)°	T = 297 K
V = 4334.9 (6) Å³	Block, colorless
Z = 4	0.22 × 0.2 × 0.12 mm

Data collection top

Bruker D8 Venture CMOS diffractometer	3441 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.040
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θ_max = 25.8°, θ_min = 2.6°
T_min = 0.715, T_max = 0.745	h = −28→28
99597 measured reflections	k = −10→10
4126 independent reflections	l = −28→28

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.0623P)² + 3.3312P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.140	(Δ/σ)_max = 0.001
S = 1.06	Δρ_max = 0.50 e Å⁻³
4126 reflections	Δρ_min = −0.29 e Å⁻³
354 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
114 restraints	Extinction coefficient: 0.0057 (13)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O3	0.43377 (5)	0.84230 (16)	0.40787 (6)	0.0547 (4)
O4	0.52519 (5)	0.82545 (19)	0.40300 (6)	0.0650 (4)
N1	0.15205 (7)	0.5819 (2)	0.16972 (7)	0.0540 (4)
H1	0.1284 (8)	0.542 (2)	0.1349 (6)	0.065*
N2	0.40861 (6)	0.56750 (17)	0.34003 (6)	0.0444 (4)
H2	0.4151 (9)	0.6559 (16)	0.3614 (8)	0.053*
C3	0.19478 (8)	0.6147 (2)	0.33073 (8)	0.0533 (5)
C4	0.14362 (9)	0.5733 (3)	0.34114 (10)	0.0683 (6)
H4	0.144072	0.571251	0.381042	0.082*
C5	0.09055 (9)	0.5341 (3)	0.29169 (12)	0.0705 (6)
H5	0.055901	0.506800	0.299318	0.085*
C6	0.08822 (8)	0.5348 (2)	0.23271 (10)	0.0590 (5)
H6	0.052601	0.509456	0.200080	0.071*
C7	0.14110 (7)	0.5749 (2)	0.22293 (8)	0.0467 (4)
C8	0.19553 (7)	0.61618 (19)	0.27159 (8)	0.0432 (4)
C9	0.24029 (7)	0.6461 (2)	0.24481 (8)	0.0450 (4)
C10	0.21169 (8)	0.6216 (2)	0.18357 (9)	0.0537 (5)
H10	0.230151	0.630485	0.154837	0.064*
C11	0.30631 (7)	0.6867 (2)	0.27697 (9)	0.0496 (4)
H11A	0.310383	0.771998	0.306092	0.060*
H11B	0.323061	0.722895	0.247150	0.060*
C12	0.34109 (7)	0.5424 (2)	0.31047 (9)	0.0480 (4)
H12A	0.325670	0.511823	0.341969	0.058*
H12B	0.333443	0.455047	0.281562	0.058*
C16	0.43581 (9)	0.4308 (3)	0.38317 (11)	0.0664 (6)
H16A	0.417335	0.427499	0.413909	0.080*
H16B	0.425604	0.332482	0.360012	0.080*
C17	0.50234 (11)	0.4390 (3)	0.41471 (13)	0.0871 (8)
H17	0.519123	0.527455	0.438803	0.105*
C18	0.53850 (14)	0.3276 (5)	0.41018 (19)	0.1316 (14)
H18A	0.522600	0.238260	0.386311	0.158*
H18B	0.580261	0.337274	0.430818	0.158*
C19	0.48981 (7)	0.8722 (2)	0.42812 (8)	0.0467 (4)
C20	0.51576 (7)	0.9709 (2)	0.48471 (8)	0.0479 (4)
H20	0.557205	0.992472	0.499179	0.057*
O5	0.6457 (5)	0.730 (3)	0.5379 (4)	0.097 (5)	0.48 (4)
O6	0.6402 (8)	0.822 (2)	0.4447 (8)	0.062 (2)	0.48 (4)
H6A	0.603390	0.828442	0.436178	0.094*	0.48 (4)
C21	0.6647 (8)	0.748 (3)	0.4963 (7)	0.060 (3)	0.48 (4)
O5A	0.6392 (3)	0.645 (2)	0.5186 (10)	0.103 (4)	0.52 (4)
O6A	0.6418 (7)	0.800 (3)	0.4512 (8)	0.084 (4)	0.52 (4)
H6AA	0.605462	0.793944	0.444863	0.126*	0.52 (4)
C21A	0.6724 (9)	0.727 (3)	0.5011 (8)	0.070 (4)	0.52 (4)
C22	0.73480 (9)	0.7230 (3)	0.51577 (9)	0.0637 (6)
H22	0.755398	0.666681	0.551626	0.076*	0.48 (4)
H22A	0.757554	0.675587	0.553077	0.076*	0.52 (4)
C13	0.43825 (8)	0.5987 (3)	0.29456 (9)	0.0579 (5)
H13A	0.470397	0.672837	0.316182	0.069*	0.099 (4)
H13B	0.458837	0.499336	0.294117	0.069*	0.099 (4)
H13C	0.427809	0.705354	0.278487	0.069*	0.901 (4)
H13D	0.481992	0.594839	0.315899	0.069*	0.901 (4)
C14	0.4188 (10)	0.652 (3)	0.2307 (5)	0.0769 (8)	0.099 (4)
H14	0.423405	0.761671	0.228839	0.092*	0.099 (4)
C15	0.397 (3)	0.592 (7)	0.1760 (14)	0.1028 (15)	0.099 (4)
H15A	0.390253	0.483222	0.170924	0.123*	0.099 (4)
H15B	0.388512	0.657311	0.141789	0.123*	0.099 (4)
C14A	0.42144 (12)	0.4880 (3)	0.24310 (12)	0.0769 (8)	0.901 (4)
H14A	0.428767	0.380233	0.251180	0.092*	0.901 (4)
C15A	0.3967 (3)	0.5342 (6)	0.18674 (15)	0.1028 (15)	0.901 (4)
H15C	0.389088	0.641456	0.177808	0.123*	0.901 (4)
H15D	0.386609	0.460156	0.155046	0.123*	0.901 (4)
O1	0.2254 (8)	0.8833 (10)	0.3924 (13)	0.099 (6)	0.38 (4)
O2	0.2527 (6)	0.645 (2)	0.3753 (9)	0.071 (5)	0.38 (4)
C1	0.3155 (7)	0.789 (2)	0.4602 (7)	0.066 (4)	0.38 (4)
H1A	0.333536	0.689257	0.477037	0.098*	0.38 (4)
H1B	0.313766	0.856311	0.492675	0.098*	0.38 (4)
H1C	0.339598	0.839519	0.440153	0.098*	0.38 (4)
C2	0.2529 (8)	0.7621 (19)	0.4148 (8)	0.064 (6)	0.38 (4)
O1A	0.2133 (4)	0.848 (2)	0.4172 (7)	0.102 (4)	0.62 (4)
O2A	0.2484 (4)	0.6422 (12)	0.3825 (6)	0.063 (2)	0.62 (4)
C1A	0.3206 (6)	0.772 (2)	0.4660 (6)	0.113 (5)	0.62 (4)
H1AA	0.350811	0.753864	0.448371	0.170*	0.62 (4)
H1AB	0.321755	0.687720	0.493898	0.170*	0.62 (4)
H1AC	0.328772	0.871404	0.487805	0.170*	0.62 (4)
C2A	0.2590 (5)	0.7784 (14)	0.4159 (6)	0.071 (4)	0.62 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0303 (6)	0.0649 (8)	0.0582 (7)	−0.0035 (5)	0.0039 (5)	−0.0155 (6)
O4	0.0370 (7)	0.0920 (11)	0.0605 (8)	−0.0001 (6)	0.0115 (6)	−0.0220 (7)
N1	0.0411 (8)	0.0576 (9)	0.0510 (9)	0.0042 (7)	0.0024 (6)	−0.0055 (7)
N2	0.0326 (7)	0.0479 (8)	0.0502 (8)	−0.0044 (6)	0.0122 (6)	−0.0050 (6)
C3	0.0375 (9)	0.0627 (11)	0.0553 (10)	0.0019 (8)	0.0119 (8)	−0.0016 (9)
C4	0.0538 (11)	0.0892 (16)	0.0675 (13)	−0.0008 (11)	0.0288 (10)	0.0034 (11)
C5	0.0405 (10)	0.0807 (15)	0.0945 (16)	−0.0076 (10)	0.0299 (11)	−0.0024 (12)
C6	0.0314 (8)	0.0566 (11)	0.0806 (14)	−0.0009 (8)	0.0108 (8)	−0.0072 (10)
C7	0.0343 (8)	0.0396 (9)	0.0584 (10)	0.0039 (6)	0.0079 (7)	−0.0025 (7)
C8	0.0313 (8)	0.0403 (8)	0.0528 (9)	0.0026 (6)	0.0095 (7)	−0.0019 (7)
C9	0.0348 (8)	0.0417 (9)	0.0553 (10)	0.0021 (7)	0.0128 (7)	−0.0009 (7)
C10	0.0468 (10)	0.0573 (11)	0.0553 (10)	0.0048 (8)	0.0170 (8)	0.0018 (8)
C11	0.0353 (8)	0.0457 (9)	0.0664 (11)	−0.0047 (7)	0.0170 (8)	−0.0052 (8)
C12	0.0307 (8)	0.0488 (9)	0.0624 (10)	−0.0065 (7)	0.0147 (7)	−0.0048 (8)
C16	0.0520 (11)	0.0612 (12)	0.0793 (14)	−0.0024 (9)	0.0163 (10)	0.0168 (10)
C17	0.0572 (13)	0.0821 (16)	0.0994 (18)	−0.0041 (12)	0.0022 (12)	0.0325 (14)
C18	0.0713 (18)	0.136 (3)	0.169 (4)	0.0369 (19)	0.021 (2)	0.068 (3)
C19	0.0323 (8)	0.0518 (10)	0.0467 (9)	0.0012 (7)	0.0035 (7)	−0.0023 (7)
C20	0.0288 (7)	0.0548 (10)	0.0505 (9)	−0.0047 (7)	0.0033 (6)	−0.0049 (8)
O5	0.053 (3)	0.178 (11)	0.073 (3)	0.018 (5)	0.037 (2)	0.035 (4)
O6	0.039 (4)	0.086 (4)	0.055 (4)	0.004 (3)	0.009 (3)	0.024 (3)
C21	0.021 (3)	0.104 (9)	0.054 (4)	0.014 (4)	0.014 (3)	0.030 (5)
O5A	0.055 (2)	0.139 (8)	0.120 (7)	−0.005 (3)	0.039 (3)	0.053 (6)
O6A	0.033 (4)	0.140 (11)	0.079 (6)	0.007 (4)	0.021 (4)	0.032 (5)
C21A	0.051 (8)	0.085 (5)	0.073 (6)	0.012 (5)	0.021 (5)	0.019 (5)
C22	0.0401 (10)	0.0906 (15)	0.0582 (11)	0.0058 (10)	0.0156 (8)	0.0138 (11)
C13	0.0387 (9)	0.0753 (13)	0.0602 (11)	−0.0093 (9)	0.0190 (8)	−0.0079 (10)
C14	0.0792 (17)	0.0819 (17)	0.0850 (19)	−0.0242 (14)	0.0481 (15)	−0.0265 (14)
C15	0.0831 (18)	0.165 (4)	0.0664 (19)	−0.026 (3)	0.0341 (17)	−0.027 (2)
C14A	0.0792 (17)	0.0819 (17)	0.0850 (19)	−0.0242 (14)	0.0481 (15)	−0.0265 (14)
C15A	0.0831 (18)	0.165 (4)	0.0664 (19)	−0.026 (3)	0.0341 (17)	−0.027 (2)
O1	0.087 (5)	0.069 (4)	0.116 (10)	−0.002 (3)	0.006 (6)	−0.008 (4)
O2	0.043 (4)	0.126 (10)	0.045 (4)	−0.007 (5)	0.015 (3)	−0.025 (5)
C1	0.052 (7)	0.099 (8)	0.046 (5)	−0.009 (6)	0.018 (6)	−0.016 (5)
C2	0.040 (6)	0.086 (11)	0.048 (7)	−0.005 (6)	−0.005 (5)	0.004 (6)
O1A	0.076 (3)	0.111 (6)	0.101 (5)	0.016 (3)	0.013 (3)	−0.032 (4)
O2A	0.040 (2)	0.090 (4)	0.052 (4)	0.012 (3)	0.009 (2)	−0.005 (3)
C1A	0.067 (5)	0.168 (12)	0.075 (5)	−0.018 (6)	−0.009 (4)	−0.013 (6)
C2A	0.066 (6)	0.079 (6)	0.070 (6)	−0.022 (4)	0.027 (5)	−0.014 (4)

Geometric parameters (Å, º) top

O3—C19	1.2583 (19)	C20—H20	0.9300
O4—C19	1.251 (2)	O5—C21	1.223 (9)
N1—H1	0.868 (10)	O6—H6A	0.8200
N1—C7	1.363 (2)	O6—C21	1.289 (8)
N1—C10	1.368 (2)	C21—C22	1.564 (18)
N2—H2	0.878 (9)	O5A—C21A	1.221 (10)
N2—C12	1.5038 (19)	O6A—H6AA	0.8200
N2—C16	1.510 (2)	O6A—C21A	1.285 (8)
N2—C13	1.498 (2)	C21A—C22	1.388 (19)
C3—C4	1.365 (3)	C22—C22ⁱⁱ	1.288 (4)
C3—C8	1.391 (3)	C22—H22	0.9300
C3—O2	1.407 (9)	C22—H22A	0.9300
C3—O2A	1.413 (6)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C4—C5	1.398 (3)	C13—H13C	0.9700
C5—H5	0.9300	C13—H13D	0.9700
C5—C6	1.361 (3)	C13—C14	1.465 (10)
C6—H6	0.9300	C13—C14A	1.458 (3)
C6—C7	1.394 (3)	C14—H14	0.9300
C7—C8	1.413 (2)	C14—C15	1.294 (10)
C8—C9	1.438 (2)	C15—H15A	0.9300
C9—C10	1.357 (3)	C15—H15B	0.9300
C9—C11	1.503 (2)	C14A—H14A	0.9300
C10—H10	0.9300	C14A—C15A	1.290 (4)
C11—H11A	0.9700	C15A—H15C	0.9300
C11—H11B	0.9700	C15A—H15D	0.9300
C11—C12	1.514 (2)	O1—C2	1.220 (10)
C12—H12A	0.9700	O2—C2	1.348 (9)
C12—H12B	0.9700	C1—H1A	0.9600
C16—H16A	0.9700	C1—H1B	0.9600
C16—H16B	0.9700	C1—H1C	0.9600
C16—C17	1.474 (3)	C1—C2	1.489 (9)
C17—H17	0.9300	O1A—C2A	1.239 (9)
C17—C18	1.300 (4)	O2A—C2A	1.359 (7)
C18—H18A	0.9300	C1A—H1AA	0.9600
C18—H18B	0.9300	C1A—H1AB	0.9600
C19—C20	1.491 (2)	C1A—H1AC	0.9600
C20—C20ⁱ	1.304 (3)	C1A—C2A	1.498 (8)

C7—N1—H1	124.6 (14)	C19—C20—H20	117.8
C7—N1—C10	108.71 (15)	C20ⁱ—C20—C19	124.40 (19)
C10—N1—H1	124.6 (14)	C20ⁱ—C20—H20	117.8
C12—N2—H2	108.3 (13)	C21—O6—H6A	109.5
C12—N2—C16	108.62 (13)	O5—C21—O6	129.4 (19)
C16—N2—H2	108.9 (13)	O5—C21—C22	114.3 (14)
C13—N2—H2	103.1 (13)	O6—C21—C22	113.7 (10)
C13—N2—C12	113.22 (14)	C21A—O6A—H6AA	109.5
C13—N2—C16	114.38 (15)	O5A—C21A—O6A	111 (2)
C4—C3—C8	121.14 (17)	O5A—C21A—C22	131.5 (18)
C4—C3—O2	126.9 (12)	O6A—C21A—C22	115.3 (11)
C4—C3—O2A	117.6 (8)	C21—C22—H22	118.6
C8—C3—O2	111.7 (12)	C21A—C22—H22A	115.9
C8—C3—O2A	121.0 (8)	C22ⁱⁱ—C22—C21	122.7 (5)
C3—C4—H4	120.1	C22ⁱⁱ—C22—C21A	128.2 (7)
C3—C4—C5	119.9 (2)	C22ⁱⁱ—C22—H22	118.6
C5—C4—H4	120.1	C22ⁱⁱ—C22—H22A	115.9
C4—C5—H5	119.1	N2—C13—H13A	103.0
C6—C5—C4	121.79 (18)	N2—C13—H13B	103.0
C6—C5—H5	119.1	N2—C13—H13C	108.6
C5—C6—H6	121.2	N2—C13—H13D	108.6
C5—C6—C7	117.65 (18)	H13A—C13—H13B	105.1
C7—C6—H6	121.2	H13C—C13—H13D	107.6
N1—C7—C6	130.13 (17)	C14—C13—N2	136.6 (9)
N1—C7—C8	107.57 (15)	C14—C13—H13A	103.0
C6—C7—C8	122.29 (18)	C14—C13—H13B	103.0
C3—C8—C7	117.24 (15)	C14A—C13—N2	114.71 (17)
C3—C8—C9	135.79 (15)	C14A—C13—H13C	108.6
C7—C8—C9	106.93 (15)	C14A—C13—H13D	108.6
C8—C9—C11	128.22 (16)	C13—C14—H14	110.7
C10—C9—C8	105.82 (15)	C15—C14—C13	139 (3)
C10—C9—C11	125.87 (16)	C15—C14—H14	110.7
N1—C10—H10	124.5	C14—C15—H15A	120.0
C9—C10—N1	110.92 (16)	C14—C15—H15B	120.0
C9—C10—H10	124.5	H15A—C15—H15B	120.0
C9—C11—H11A	109.6	C13—C14A—H14A	118.8
C9—C11—H11B	109.6	C15A—C14A—C13	122.3 (3)
C9—C11—C12	110.08 (14)	C15A—C14A—H14A	118.8
H11A—C11—H11B	108.2	C14A—C15A—H15C	120.0
C12—C11—H11A	109.6	C14A—C15A—H15D	120.0
C12—C11—H11B	109.6	H15C—C15A—H15D	120.0
N2—C12—C11	114.08 (14)	C2—O2—C3	113.5 (14)
N2—C12—H12A	108.7	H1A—C1—H1B	109.5
N2—C12—H12B	108.7	H1A—C1—H1C	109.5
C11—C12—H12A	108.7	H1B—C1—H1C	109.5
C11—C12—H12B	108.7	C2—C1—H1A	109.5
H12A—C12—H12B	107.6	C2—C1—H1B	109.5
N2—C16—H16A	108.7	C2—C1—H1C	109.5
N2—C16—H16B	108.7	O1—C2—O2	117 (2)
H16A—C16—H16B	107.6	O1—C2—C1	114.3 (18)
C17—C16—N2	114.37 (17)	O2—C2—C1	110.6 (12)
C17—C16—H16A	108.7	C2A—O2A—C3	123.3 (8)
C17—C16—H16B	108.7	H1AA—C1A—H1AB	109.5
C16—C17—H17	118.7	H1AA—C1A—H1AC	109.5
C18—C17—C16	122.6 (3)	H1AB—C1A—H1AC	109.5
C18—C17—H17	118.7	C2A—C1A—H1AA	109.5
C17—C18—H18A	120.0	C2A—C1A—H1AB	109.5
C17—C18—H18B	120.0	C2A—C1A—H1AC	109.5
H18A—C18—H18B	120.0	O1A—C2A—O2A	115.7 (14)
O3—C19—C20	118.57 (15)	O1A—C2A—C1A	127.1 (11)
O4—C19—O3	123.72 (16)	O2A—C2A—C1A	110.0 (9)
O4—C19—C20	117.70 (14)

O3—C19—C20—C20ⁱ	0.2 (3)	C8—C3—O2—C2	128.5 (19)
O4—C19—C20—C20ⁱ	179.3 (2)	C8—C3—O2A—C2A	107.5 (16)
N1—C7—C8—C3	−179.21 (16)	C8—C9—C10—N1	1.3 (2)
N1—C7—C8—C9	−0.90 (18)	C8—C9—C11—C12	71.7 (2)
N2—C16—C17—C18	−121.8 (3)	C9—C11—C12—N2	175.40 (14)
N2—C13—C14—C15	−86 (5)	C10—N1—C7—C6	−177.82 (19)
N2—C13—C14A—C15A	121.5 (3)	C10—N1—C7—C8	1.7 (2)
C3—C4—C5—C6	0.4 (4)	C10—C9—C11—C12	−104.3 (2)
C3—C8—C9—C10	177.6 (2)	C11—C9—C10—N1	178.07 (16)
C3—C8—C9—C11	1.0 (3)	C12—N2—C16—C17	179.1 (2)
C3—O2—C2—O1	−47 (4)	C12—N2—C13—C14	20.0 (14)
C3—O2—C2—C1	−179.5 (18)	C12—N2—C13—C14A	−48.3 (2)
C3—O2A—C2A—O1A	29 (3)	C16—N2—C12—C11	167.33 (16)
C3—O2A—C2A—C1A	−177.9 (14)	C16—N2—C13—C14	145.2 (14)
C4—C3—C8—C7	0.7 (3)	C16—N2—C13—C14A	76.8 (2)
C4—C3—C8—C9	−177.0 (2)	O5—C21—C22—C22ⁱⁱ	−160.9 (18)
C4—C3—O2—C2	−57 (3)	O6—C21—C22—C22ⁱⁱ	3 (2)
C4—C3—O2A—C2A	−78.0 (17)	O5A—C21A—C22—C22ⁱⁱ	158 (2)
C4—C5—C6—C7	0.6 (3)	O6A—C21A—C22—C22ⁱⁱ	−4 (3)
C5—C6—C7—N1	178.49 (19)	C13—N2—C12—C11	−64.5 (2)
C5—C6—C7—C8	−1.0 (3)	C13—N2—C16—C17	51.5 (3)
C6—C7—C8—C3	0.4 (3)	O2—C3—C4—C5	−174.8 (10)
C6—C7—C8—C9	178.68 (16)	O2—C3—C8—C7	175.3 (9)
C7—N1—C10—C9	−2.0 (2)	O2—C3—C8—C9	−2.4 (9)
C7—C8—C9—C10	−0.25 (19)	O2A—C3—C4—C5	−175.5 (5)
C7—C8—C9—C11	−176.89 (16)	O2A—C3—C8—C7	175.0 (5)
C8—C3—C4—C5	−1.1 (3)	O2A—C3—C8—C9	−2.7 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱⁱⁱ	0.87 (1)	2.22 (2)	2.962 (2)	144 (2)
N2—H2···O3	0.88 (1)	1.87 (1)	2.7446 (19)	177 (2)
O6—H6A···O4	0.82	1.72	2.530 (17)	168
O6A—H6AA···O4	0.82	1.81	2.577 (16)	156

Symmetry code: (iii) −x+1/2, y−1/2, −z+1/2.

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Psilacetin derivatives: fumarate salts of the meth­yl–ethyl, meth­yl–allyl and diallyl variants of the psilocin prodrug

Supporting information

Key indicators

checkCIF/PLATON results

Psilacetin derivatives: fumarate salts of the methyl–ethyl, methyl–allyl and diallyl variants of the psilocin prodrug