The methanol and ethanol solvates of 4-glutarato-N,N-diiso­propyl­tryptamine

The structures of two solvates of the zwitterionic prodrug of the psychedelic 4-HO-DiPT are reported.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.143
• Data-to-parameter ratio = 15.4

Structure: II

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.060
• wR factor = 0.176
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Datablock: umd2538h_a



Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter Within Range of ...      3.062 Sigma
PLAT260_ALERT_2_C Large Average Ueq of Residue Including        O5      0.110 Check
PLAT414_ALERT_2_C Short Intra D-H..H-X       H5A      ..H22C     .       1.94 Ang.
                                                      x,y,z  =      1_555 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.320 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          9 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          6 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          3 Report
PLAT432_ALERT_2_G Short Inter X...Y Contact  O5       ..C17      .       2.98 Ang.
                                                 -x,1-y,1-z  =      3_566 Check
PLAT767_ALERT_4_G INS Embedded LIST 6 Instruction Should be LIST 4     Please Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          3 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          1 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          7 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Info

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

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




Datablock: umd2577k_a



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C21 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including        O5      0.111 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.627 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          6 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          1 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       4.78 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  3  )       4.22 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT767_ALERT_4_G INS Embedded LIST 6 Instruction Should be LIST 4     Please Check
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C2 H6 O
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          3 Note
              C2 H6 O
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         46 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
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         14 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          2 Check

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

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

---

Computing details

For both structures, data collection: APEX4 (Bruker, 2021); cell refinement: SAINT (Bruker, 2021); data reduction: SAINT (Bruker, 2021); 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).

5-[(3-{2-[Bis(propan-2-yl)azaniumyl]ethyl}-1H-indol-4-yl)oxy]-5-oxopentanoate methanol monosolvate (I)

Crystal data

C21H30N2O4·CH4O	F(000) = 880
Mr = 406.51	Dx = 1.194 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.9531 (5) Å	Cell parameters from 9859 reflections
b = 13.4224 (7) Å	θ = 3.0–25.6°
c = 21.2015 (11) Å	µ = 0.08 mm^−1
β = 92.484 (2)°	T = 297 K
V = 2261.1 (2) Å^3	Block, colourless
Z = 4	0.22 × 0.21 × 0.20 mm

Data collection

Bruker D8 Venture CMOS diffractometer	3531 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.039
Absorption correction: multi-scan (SADABS; Bruker, 2021)	θmax = 25.7°, θmin = 3.0°
Tmin = 0.718, Tmax = 0.745	h = −9→9
61210 measured reflections	k = −16→16
4304 independent reflections	l = −25→25

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0677P)^2 + 1.0658P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.143	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.46 e Å^−3
4304 reflections	Δρmin = −0.39 e Å^−3
279 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.0049 (16)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.17552 (17)	0.35382 (9)	0.29846 (5)	0.0421 (3)
O2	0.2385 (2)	0.51443 (11)	0.28621 (6)	0.0675 (5)
O3	0.3521 (2)	0.72404 (12)	0.48361 (7)	0.0730 (5)
O4	0.2931 (2)	0.66404 (11)	0.57648 (6)	0.0621 (4)
N1	0.4481 (2)	0.26115 (12)	0.11776 (7)	0.0454 (4)
N2	0.61740 (18)	0.15461 (10)	0.37628 (6)	0.0362 (3)
C1	0.5573 (2)	0.25778 (14)	0.16893 (9)	0.0446 (4)
H1A	0.669647	0.238884	0.167694	0.053*
C2	0.2940 (2)	0.29148 (13)	0.13645 (8)	0.0386 (4)
C3	0.1426 (3)	0.30411 (15)	0.10225 (8)	0.0481 (5)
H3	0.134321	0.291932	0.059041	0.058*
C4	0.0058 (3)	0.33510 (17)	0.13421 (9)	0.0539 (5)
H4	−0.096839	0.343720	0.112189	0.065*
C5	0.0169 (2)	0.35412 (15)	0.19936 (9)	0.0489 (5)
H5	−0.077222	0.375904	0.219944	0.059*
C6	0.1662 (2)	0.34057 (12)	0.23242 (8)	0.0375 (4)
C7	0.3099 (2)	0.30850 (12)	0.20252 (7)	0.0348 (4)
C8	0.4801 (2)	0.28580 (12)	0.22217 (8)	0.0381 (4)
C9	0.5583 (2)	0.27857 (13)	0.28772 (8)	0.0410 (4)
H9A	0.501378	0.323224	0.315755	0.049*
H9B	0.675960	0.297597	0.287599	0.049*
C10	0.5426 (2)	0.17173 (13)	0.31047 (8)	0.0387 (4)
H10A	0.424472	0.153645	0.309562	0.046*
H10B	0.598183	0.128085	0.281434	0.046*
C11	0.4906 (2)	0.10852 (14)	0.41929 (9)	0.0452 (4)
H11	0.547211	0.100130	0.460941	0.054*
C13	0.3444 (3)	0.17846 (17)	0.42725 (11)	0.0581 (5)
H13A	0.385521	0.241480	0.442784	0.087*
H13B	0.269327	0.150484	0.456783	0.087*
H13C	0.285274	0.187901	0.387253	0.087*
C12	0.4347 (4)	0.00616 (17)	0.39679 (13)	0.0723 (7)
H12A	0.530499	−0.037275	0.396077	0.108*
H12B	0.383512	0.011193	0.355068	0.108*
H12C	0.354637	−0.020317	0.424972	0.108*
C14	0.7823 (2)	0.09675 (15)	0.37460 (9)	0.0471 (5)
H14	0.759363	0.032539	0.353974	0.057*
C15	0.8546 (3)	0.0769 (2)	0.44071 (11)	0.0712 (7)
H15A	0.783385	0.030922	0.461678	0.107*
H15B	0.861037	0.138280	0.463944	0.107*
H15C	0.965311	0.048954	0.438396	0.107*
C16	0.9078 (3)	0.15321 (19)	0.33620 (12)	0.0632 (6)
H16A	0.862701	0.161671	0.293803	0.095*
H16B	1.011172	0.116333	0.335554	0.095*
H16C	0.929013	0.217350	0.354941	0.095*
C17	0.2114 (2)	0.44694 (13)	0.32012 (8)	0.0409 (4)
C18	0.2177 (3)	0.44943 (14)	0.39084 (8)	0.0483 (5)
H18A	0.306025	0.404959	0.406611	0.058*
H18B	0.111785	0.424768	0.405632	0.058*
C19	0.2497 (3)	0.55192 (15)	0.41772 (9)	0.0522 (5)
H19A	0.162315	0.596552	0.401363	0.063*
H19B	0.356367	0.576115	0.403349	0.063*
C20	0.2538 (3)	0.55546 (15)	0.48899 (9)	0.0536 (5)
H20A	0.332027	0.505235	0.505171	0.064*
H20B	0.143059	0.538020	0.502980	0.064*
C21	0.3041 (3)	0.65529 (15)	0.51767 (9)	0.0474 (5)
O5	0.1577 (3)	0.53742 (16)	0.66260 (11)	0.0928 (6)
H5A	0.224 (4)	0.563 (2)	0.6271 (11)	0.111*
C22	0.2529 (6)	0.4611 (3)	0.6828 (2)	0.1272 (15)
H22A	0.184260	0.413329	0.703499	0.191*
H22B	0.339437	0.484832	0.712036	0.191*
H22C	0.303585	0.430125	0.647521	0.191*
H2	0.644 (2)	0.2153 (9)	0.3923 (9)	0.045 (5)*
H1	0.475 (3)	0.2488 (16)	0.0796 (6)	0.057 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0613 (8)	0.0378 (6)	0.0278 (6)	−0.0046 (6)	0.0104 (5)	−0.0059 (5)
O2	0.1172 (14)	0.0483 (8)	0.0375 (7)	−0.0279 (9)	0.0073 (8)	0.0011 (6)
O3	0.1127 (14)	0.0647 (10)	0.0436 (8)	−0.0400 (9)	0.0275 (8)	−0.0135 (7)
O4	0.1033 (12)	0.0526 (8)	0.0311 (7)	−0.0267 (8)	0.0110 (7)	−0.0100 (6)
N1	0.0607 (10)	0.0477 (9)	0.0289 (7)	0.0035 (7)	0.0133 (7)	−0.0045 (6)
N2	0.0427 (8)	0.0336 (7)	0.0321 (7)	−0.0030 (6)	−0.0009 (6)	−0.0024 (6)
C1	0.0484 (10)	0.0436 (10)	0.0421 (10)	0.0040 (8)	0.0068 (8)	−0.0017 (8)
C2	0.0537 (10)	0.0338 (8)	0.0286 (8)	−0.0027 (7)	0.0058 (7)	−0.0025 (6)
C3	0.0624 (12)	0.0538 (11)	0.0278 (8)	−0.0041 (9)	−0.0028 (8)	−0.0026 (8)
C4	0.0502 (11)	0.0655 (13)	0.0452 (11)	−0.0023 (10)	−0.0074 (9)	0.0017 (9)
C5	0.0455 (10)	0.0558 (11)	0.0460 (11)	0.0010 (9)	0.0075 (8)	−0.0030 (9)
C6	0.0500 (10)	0.0347 (8)	0.0283 (8)	−0.0044 (7)	0.0073 (7)	−0.0033 (6)
C7	0.0476 (9)	0.0301 (8)	0.0266 (8)	−0.0030 (7)	0.0026 (7)	−0.0017 (6)
C8	0.0480 (10)	0.0333 (8)	0.0331 (8)	−0.0006 (7)	0.0028 (7)	−0.0002 (7)
C9	0.0477 (10)	0.0379 (9)	0.0370 (9)	−0.0015 (7)	−0.0027 (7)	−0.0032 (7)
C10	0.0440 (9)	0.0398 (9)	0.0318 (8)	−0.0042 (7)	−0.0027 (7)	−0.0033 (7)
C11	0.0531 (11)	0.0423 (10)	0.0404 (9)	−0.0060 (8)	0.0054 (8)	0.0046 (8)
C13	0.0523 (12)	0.0638 (13)	0.0592 (13)	−0.0052 (10)	0.0121 (10)	−0.0035 (10)
C12	0.0905 (18)	0.0434 (12)	0.0845 (17)	−0.0185 (12)	0.0207 (14)	0.0013 (11)
C14	0.0463 (10)	0.0472 (10)	0.0475 (10)	0.0064 (8)	−0.0030 (8)	−0.0041 (8)
C15	0.0655 (15)	0.0859 (17)	0.0609 (14)	0.0185 (13)	−0.0131 (11)	0.0064 (12)
C16	0.0448 (11)	0.0772 (16)	0.0678 (14)	0.0022 (10)	0.0058 (10)	−0.0027 (12)
C17	0.0503 (10)	0.0382 (9)	0.0349 (9)	−0.0052 (8)	0.0075 (7)	−0.0045 (7)
C18	0.0719 (13)	0.0414 (10)	0.0319 (9)	−0.0056 (9)	0.0054 (8)	−0.0059 (7)
C19	0.0747 (14)	0.0454 (11)	0.0367 (10)	−0.0082 (9)	0.0036 (9)	−0.0102 (8)
C20	0.0731 (14)	0.0505 (11)	0.0380 (10)	−0.0169 (10)	0.0104 (9)	−0.0105 (8)
C21	0.0573 (11)	0.0509 (11)	0.0349 (9)	−0.0159 (9)	0.0107 (8)	−0.0100 (8)
O5	0.0849 (13)	0.0864 (14)	0.1090 (16)	0.0042 (11)	0.0245 (11)	0.0304 (12)
C22	0.152 (4)	0.073 (2)	0.159 (4)	0.045 (2)	0.036 (3)	0.038 (2)

Geometric parameters (Å, º)

O1—C6	1.4100 (19)	C11—C12	1.515 (3)
O1—C17	1.358 (2)	C13—H13A	0.9600
O2—C17	1.182 (2)	C13—H13B	0.9600
O3—C21	1.242 (2)	C13—H13C	0.9600
O4—C21	1.259 (2)	C12—H12A	0.9600
N1—C1	1.361 (2)	C12—H12B	0.9600
N1—C2	1.366 (2)	C12—H12C	0.9600
N1—H1	0.862 (9)	C14—H14	0.9800
N2—C10	1.510 (2)	C14—C15	1.515 (3)
N2—C11	1.520 (2)	C14—C16	1.518 (3)
N2—C14	1.526 (2)	C15—H15A	0.9600
N2—H2	0.903 (9)	C15—H15B	0.9600
C1—H1A	0.9300	C15—H15C	0.9600
C1—C8	1.361 (2)	C16—H16A	0.9600
C2—C3	1.389 (3)	C16—H16B	0.9600
C2—C7	1.420 (2)	C16—H16C	0.9600
C3—H3	0.9300	C17—C18	1.498 (2)
C3—C4	1.371 (3)	C18—H18A	0.9700
C4—H4	0.9300	C18—H18B	0.9700
C4—C5	1.404 (3)	C18—C19	1.506 (3)
C5—H5	0.9300	C19—H19A	0.9700
C5—C6	1.364 (3)	C19—H19B	0.9700
C6—C7	1.399 (2)	C19—C20	1.511 (3)
C7—C8	1.431 (3)	C20—H20A	0.9700
C8—C9	1.501 (2)	C20—H20B	0.9700
C9—H9A	0.9700	C20—C21	1.518 (3)
C9—H9B	0.9700	O5—H5A	0.998 (10)
C9—C10	1.520 (2)	O5—C22	1.334 (4)
C10—H10A	0.9700	C22—H22A	0.9600
C10—H10B	0.9700	C22—H22B	0.9600
C11—H11	0.9800	C22—H22C	0.9600
C11—C13	1.510 (3)
C17—O1—C6	116.95 (13)	H13B—C13—H13C	109.5
C1—N1—C2	109.15 (14)	C11—C12—H12A	109.5
C1—N1—H1	124.4 (15)	C11—C12—H12B	109.5
C2—N1—H1	126.4 (15)	C11—C12—H12C	109.5
C10—N2—C11	111.80 (14)	H12A—C12—H12B	109.5
C10—N2—C14	111.11 (13)	H12A—C12—H12C	109.5
C10—N2—H2	106.6 (13)	H12B—C12—H12C	109.5
C11—N2—C14	113.58 (14)	N2—C14—H14	108.3
C11—N2—H2	106.8 (13)	C15—C14—N2	111.09 (16)
C14—N2—H2	106.4 (13)	C15—C14—H14	108.3
N1—C1—H1A	124.6	C15—C14—C16	110.61 (19)
N1—C1—C8	110.89 (17)	C16—C14—N2	110.14 (16)
C8—C1—H1A	124.6	C16—C14—H14	108.3
N1—C2—C3	130.79 (16)	C14—C15—H15A	109.5
N1—C2—C7	106.95 (15)	C14—C15—H15B	109.5
C3—C2—C7	122.25 (17)	C14—C15—H15C	109.5
C2—C3—H3	121.1	H15A—C15—H15B	109.5
C4—C3—C2	117.88 (17)	H15A—C15—H15C	109.5
C4—C3—H3	121.1	H15B—C15—H15C	109.5
C3—C4—H4	119.2	C14—C16—H16A	109.5
C3—C4—C5	121.60 (18)	C14—C16—H16B	109.5
C5—C4—H4	119.2	C14—C16—H16C	109.5
C4—C5—H5	120.1	H16A—C16—H16B	109.5
C6—C5—C4	119.84 (18)	H16A—C16—H16C	109.5
C6—C5—H5	120.1	H16B—C16—H16C	109.5
C5—C6—O1	120.02 (16)	O1—C17—C18	110.89 (14)
C5—C6—C7	121.21 (16)	O2—C17—O1	122.74 (16)
C7—C6—O1	118.69 (15)	O2—C17—C18	126.32 (17)
C2—C7—C8	107.19 (15)	C17—C18—H18A	108.9
C6—C7—C2	117.21 (16)	C17—C18—H18B	108.9
C6—C7—C8	135.60 (15)	C17—C18—C19	113.38 (16)
C1—C8—C7	105.81 (15)	H18A—C18—H18B	107.7
C1—C8—C9	124.48 (17)	C19—C18—H18A	108.9
C7—C8—C9	129.19 (15)	C19—C18—H18B	108.9
C8—C9—H9A	110.0	C18—C19—H19A	108.8
C8—C9—H9B	110.0	C18—C19—H19B	108.8
C8—C9—C10	108.57 (14)	C18—C19—C20	113.78 (16)
H9A—C9—H9B	108.4	H19A—C19—H19B	107.7
C10—C9—H9A	110.0	C20—C19—H19A	108.8
C10—C9—H9B	110.0	C20—C19—H19B	108.8
N2—C10—C9	113.72 (13)	C19—C20—H20A	108.5
N2—C10—H10A	108.8	C19—C20—H20B	108.5
N2—C10—H10B	108.8	C19—C20—C21	114.98 (16)
C9—C10—H10A	108.8	H20A—C20—H20B	107.5
C9—C10—H10B	108.8	C21—C20—H20A	108.5
H10A—C10—H10B	107.7	C21—C20—H20B	108.5
N2—C11—H11	107.3	O3—C21—O4	122.88 (17)
C13—C11—N2	110.38 (15)	O3—C21—C20	120.35 (16)
C13—C11—H11	107.3	O4—C21—C20	116.77 (17)
C13—C11—C12	112.46 (19)	C22—O5—H5A	101 (2)
C12—C11—N2	111.93 (16)	O5—C22—H22A	109.5
C12—C11—H11	107.3	O5—C22—H22B	109.5
C11—C13—H13A	109.5	O5—C22—H22C	109.5
C11—C13—H13B	109.5	H22A—C22—H22B	109.5
C11—C13—H13C	109.5	H22A—C22—H22C	109.5
H13A—C13—H13B	109.5	H22B—C22—H22C	109.5
H13A—C13—H13C	109.5
O1—C6—C7—C2	177.15 (14)	C6—O1—C17—O2	−2.0 (3)
O1—C6—C7—C8	−2.1 (3)	C6—O1—C17—C18	−179.77 (15)
O1—C17—C18—C19	−177.50 (17)	C6—C7—C8—C1	179.74 (19)
O2—C17—C18—C19	4.8 (3)	C6—C7—C8—C9	7.9 (3)
N1—C1—C8—C7	−0.1 (2)	C7—C2—C3—C4	0.7 (3)
N1—C1—C8—C9	172.23 (16)	C7—C8—C9—C10	90.2 (2)
N1—C2—C3—C4	179.42 (19)	C8—C9—C10—N2	179.92 (14)
N1—C2—C7—C6	179.94 (15)	C10—N2—C11—C13	−63.01 (19)
N1—C2—C7—C8	−0.61 (19)	C10—N2—C11—C12	63.1 (2)
C1—N1—C2—C3	−178.34 (19)	C10—N2—C14—C15	−178.31 (17)
C1—N1—C2—C7	0.5 (2)	C10—N2—C14—C16	58.79 (19)
C1—C8—C9—C10	−80.3 (2)	C11—N2—C10—C9	125.26 (16)
C2—N1—C1—C8	−0.3 (2)	C11—N2—C14—C15	−51.2 (2)
C2—C3—C4—C5	0.3 (3)	C11—N2—C14—C16	−174.13 (16)
C2—C7—C8—C1	0.45 (19)	C14—N2—C10—C9	−106.70 (17)
C2—C7—C8—C9	−171.42 (16)	C14—N2—C11—C13	170.27 (16)
C3—C2—C7—C6	−1.1 (2)	C14—N2—C11—C12	−63.6 (2)
C3—C2—C7—C8	178.39 (16)	C17—O1—C6—C5	−89.2 (2)
C3—C4—C5—C6	−0.8 (3)	C17—O1—C6—C7	94.06 (19)
C4—C5—C6—O1	−176.20 (17)	C17—C18—C19—C20	179.16 (18)
C4—C5—C6—C7	0.4 (3)	C18—C19—C20—C21	173.75 (19)
C5—C6—C7—C2	0.5 (2)	C19—C20—C21—O3	−6.2 (3)
C5—C6—C7—C8	−178.76 (19)	C19—C20—C21—O4	173.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4	1.00 (1)	1.83 (2)	2.748 (2)	151 (3)
N2—H2···O4^i	0.90 (1)	1.81 (1)	2.7154 (19)	177 (2)
N1—H1···O3^ii	0.86 (1)	1.99 (1)	2.773 (2)	151 (2)

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

5-[(3-{2-[Bis(propan-2-yl)azaniumyl]ethyl}-1H-indol-4-yl)oxy]-5-oxopentanoate ethanol monosolvate (II)

Crystal data

C21H30N2O4·C2H6O	F(000) = 912
Mr = 420.54	Dx = 1.156 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.0087 (12) Å	Cell parameters from 7678 reflections
b = 13.7968 (17) Å	θ = 2.5–24.9°
c = 21.878 (3) Å	µ = 0.08 mm^−1
β = 90.749 (4)°	T = 297 K
V = 2417.2 (5) Å^3	Block, colourless
Z = 4	0.30 × 0.27 × 0.22 mm

Data collection

Bruker D8 Venture CMOS diffractometer	3038 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.055
Absorption correction: multi-scan (SADABS; Bruker, 2021)	θmax = 25.4°, θmin = 2.5°
Tmin = 0.692, Tmax = 0.745	h = −9→9
37412 measured reflections	k = −16→16
4461 independent reflections	l = −26→26

Refinement

Refinement on F^2	46 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.176	w = 1/[σ^2(Fo^2) + (0.0772P)^2 + 1.2353P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4461 reflections	Δρmax = 0.35 e Å^−3
313 parameters	Δρmin = −0.46 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.2092 (2)	0.36531 (11)	0.30305 (7)	0.0553 (5)
O2	0.2584 (3)	0.52278 (14)	0.28903 (8)	0.0832 (7)
O3	0.3563 (3)	0.73209 (16)	0.48029 (8)	0.0872 (7)
O4	0.2945 (3)	0.67092 (14)	0.56965 (8)	0.0787 (7)
N1	0.4952 (3)	0.27474 (16)	0.12915 (9)	0.0595 (6)
N2	0.6135 (3)	0.16000 (15)	0.37926 (9)	0.0508 (5)
C1	0.5975 (4)	0.26944 (19)	0.17914 (11)	0.0583 (7)
H1A	0.708687	0.250056	0.178280	0.070*
C2	0.3413 (4)	0.30442 (17)	0.14673 (10)	0.0513 (6)
C3	0.1947 (4)	0.31751 (19)	0.11340 (12)	0.0630 (7)
H3	0.191217	0.307090	0.071410	0.076*
C4	0.0551 (4)	0.3462 (2)	0.14408 (13)	0.0701 (8)
H4	−0.044828	0.354362	0.122584	0.084*
C5	0.0599 (4)	0.3635 (2)	0.20711 (12)	0.0628 (7)
H5	−0.035912	0.383807	0.226972	0.075*
C6	0.2045 (3)	0.35080 (17)	0.23928 (10)	0.0504 (6)
C7	0.3503 (3)	0.31992 (15)	0.21087 (10)	0.0461 (6)
C8	0.5159 (3)	0.29619 (16)	0.23053 (10)	0.0492 (6)
C9	0.5832 (3)	0.28496 (17)	0.29440 (11)	0.0532 (6)
H9A	0.528225	0.330228	0.321445	0.064*
H9B	0.702044	0.298597	0.295389	0.064*
C10	0.5518 (3)	0.18157 (17)	0.31541 (10)	0.0513 (6)
H10A	0.432721	0.168963	0.313271	0.062*
H10B	0.605720	0.137478	0.287333	0.062*
C11	0.7716 (4)	0.0990 (2)	0.37851 (13)	0.0689 (8)
H11	0.745795	0.037954	0.357516	0.083*
C12	0.8324 (5)	0.0750 (3)	0.44274 (16)	0.0990 (12)
H12A	0.753581	0.032798	0.461969	0.148*
H12B	0.843001	0.133711	0.466050	0.148*
H12C	0.938971	0.043428	0.440839	0.148*
C13	0.9059 (4)	0.1506 (3)	0.34291 (17)	0.0903 (11)
H13A	0.866622	0.162243	0.301912	0.135*
H13B	1.004393	0.111058	0.341935	0.135*
H13C	0.931685	0.211311	0.362305	0.135*
C14	0.4773 (4)	0.11792 (19)	0.41877 (12)	0.0615 (7)
H14	0.526311	0.106134	0.459368	0.074*
C15	0.4148 (5)	0.0211 (2)	0.39449 (17)	0.0947 (12)
H15A	0.505966	−0.023937	0.393021	0.142*
H15B	0.368656	0.029758	0.354130	0.142*
H15C	0.330151	−0.003624	0.420973	0.142*
C16	0.3377 (4)	0.1903 (2)	0.42646 (14)	0.0753 (9)
H16A	0.255515	0.164077	0.453397	0.113*
H16B	0.286909	0.203677	0.387375	0.113*
H16C	0.381923	0.249228	0.443505	0.113*
C17	0.2386 (3)	0.45697 (18)	0.32284 (11)	0.0538 (6)
C18	0.2450 (4)	0.46119 (18)	0.39101 (11)	0.0596 (7)
H18A	0.336436	0.420965	0.405661	0.072*
H18B	0.142255	0.434400	0.406826	0.072*
C19	0.2678 (4)	0.56242 (19)	0.41582 (11)	0.0625 (7)
H19A	0.373719	0.587837	0.402005	0.075*
H19B	0.179984	0.603603	0.399319	0.075*
C20	0.2642 (4)	0.5668 (2)	0.48422 (11)	0.0690 (8)
H20A	0.341419	0.518749	0.500346	0.083*
H20B	0.153216	0.548829	0.497359	0.083*
C21	0.3081 (4)	0.6643 (2)	0.51231 (11)	0.0627 (7)
H2	0.640 (3)	0.217 (2)	0.3959 (12)	0.064 (8)*
H1	0.526 (3)	0.261 (2)	0.0929 (6)	0.068 (8)*
O5	−0.1278 (12)	0.4643 (7)	0.3667 (5)	0.123 (3)	0.531 (11)
H5A	−0.165922	0.438097	0.397138	0.184*	0.531 (11)
C22	−0.2489 (13)	0.5309 (7)	0.3417 (5)	0.106 (3)	0.531 (11)
H22A	−0.281815	0.577081	0.372735	0.127*	0.531 (11)
H22B	−0.347635	0.495888	0.328047	0.127*	0.531 (11)
C23	−0.1720 (13)	0.5827 (6)	0.2891 (3)	0.106 (3)	0.531 (11)
H23A	−0.251356	0.627541	0.271841	0.159*	0.531 (11)
H23B	−0.074882	0.617423	0.303038	0.159*	0.531 (11)
H23C	−0.140469	0.536518	0.258509	0.159*	0.531 (11)
O5A	−0.1337 (9)	0.4474 (4)	0.3501 (3)	0.0655 (18)	0.469 (11)
H5AA	−0.198660	0.410977	0.367474	0.098*	0.469 (11)
C22A	−0.1963 (16)	0.5437 (6)	0.3520 (4)	0.098 (3)	0.469 (11)
H22C	−0.106576	0.590542	0.356016	0.117*	0.469 (11)
H22D	−0.273691	0.552244	0.385271	0.117*	0.469 (11)
C23A	−0.2814 (13)	0.5518 (7)	0.2923 (4)	0.097 (3)	0.469 (11)
H23D	−0.329689	0.615146	0.288185	0.146*	0.469 (11)
H23E	−0.202252	0.541673	0.260303	0.146*	0.469 (11)
H23F	−0.367862	0.503720	0.289294	0.146*	0.469 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0813 (13)	0.0451 (9)	0.0399 (9)	−0.0016 (8)	0.0149 (8)	−0.0089 (7)
O2	0.142 (2)	0.0566 (12)	0.0510 (11)	−0.0251 (12)	0.0040 (12)	0.0006 (9)
O3	0.142 (2)	0.0749 (13)	0.0456 (10)	−0.0433 (13)	0.0284 (11)	−0.0115 (10)
O4	0.1303 (19)	0.0686 (12)	0.0376 (9)	−0.0367 (12)	0.0170 (10)	−0.0126 (8)
N1	0.0858 (17)	0.0567 (13)	0.0364 (11)	0.0033 (11)	0.0155 (11)	−0.0061 (9)
N2	0.0669 (14)	0.0427 (11)	0.0428 (11)	−0.0010 (10)	0.0009 (9)	−0.0050 (9)
C1	0.0704 (18)	0.0556 (15)	0.0491 (14)	0.0020 (13)	0.0113 (12)	−0.0018 (11)
C2	0.0757 (18)	0.0403 (12)	0.0382 (12)	−0.0019 (12)	0.0086 (12)	−0.0034 (10)
C3	0.090 (2)	0.0592 (16)	0.0391 (13)	−0.0040 (15)	−0.0046 (14)	−0.0045 (11)
C4	0.075 (2)	0.0740 (19)	0.0604 (17)	−0.0038 (16)	−0.0109 (15)	−0.0013 (14)
C5	0.0634 (18)	0.0629 (17)	0.0621 (16)	0.0023 (13)	0.0069 (14)	−0.0077 (13)
C6	0.0693 (17)	0.0428 (13)	0.0392 (12)	−0.0041 (11)	0.0078 (11)	−0.0071 (10)
C7	0.0662 (16)	0.0360 (11)	0.0360 (11)	−0.0054 (10)	0.0050 (10)	−0.0042 (9)
C8	0.0650 (16)	0.0410 (12)	0.0417 (12)	−0.0040 (11)	0.0050 (11)	−0.0024 (10)
C9	0.0671 (17)	0.0480 (14)	0.0444 (13)	−0.0043 (12)	0.0013 (11)	−0.0063 (10)
C10	0.0649 (16)	0.0482 (14)	0.0407 (12)	−0.0041 (12)	−0.0010 (11)	−0.0045 (10)
C11	0.078 (2)	0.0663 (18)	0.0619 (16)	0.0174 (15)	−0.0067 (14)	−0.0074 (14)
C12	0.103 (3)	0.113 (3)	0.080 (2)	0.033 (2)	−0.021 (2)	0.003 (2)
C13	0.066 (2)	0.112 (3)	0.094 (2)	0.0162 (19)	0.0070 (18)	−0.011 (2)
C14	0.081 (2)	0.0516 (14)	0.0520 (14)	−0.0085 (14)	0.0075 (13)	0.0042 (12)
C15	0.126 (3)	0.0562 (18)	0.102 (3)	−0.0246 (19)	0.022 (2)	0.0006 (17)
C16	0.078 (2)	0.076 (2)	0.0728 (19)	−0.0069 (16)	0.0166 (16)	−0.0036 (15)
C17	0.0651 (17)	0.0494 (14)	0.0470 (13)	−0.0051 (12)	0.0068 (11)	−0.0079 (11)
C18	0.0809 (19)	0.0515 (14)	0.0466 (14)	−0.0031 (13)	0.0096 (13)	−0.0091 (11)
C19	0.083 (2)	0.0556 (15)	0.0487 (14)	−0.0081 (14)	0.0050 (13)	−0.0121 (12)
C20	0.098 (2)	0.0628 (17)	0.0465 (14)	−0.0181 (15)	0.0105 (14)	−0.0130 (12)
C21	0.084 (2)	0.0624 (16)	0.0420 (13)	−0.0190 (14)	0.0143 (13)	−0.0109 (12)
O5	0.125 (4)	0.120 (4)	0.123 (4)	0.0016 (19)	0.0008 (19)	0.0101 (19)
C22	0.106 (3)	0.105 (3)	0.107 (3)	0.0010 (10)	0.0003 (10)	−0.0001 (10)
C23	0.107 (3)	0.104 (3)	0.106 (3)	0.0061 (19)	0.0028 (19)	0.0021 (19)
O5A	0.070 (2)	0.060 (2)	0.067 (2)	−0.0011 (15)	0.0075 (16)	0.0087 (16)
C22A	0.098 (3)	0.096 (3)	0.099 (3)	0.0021 (10)	0.0001 (10)	0.0004 (10)
C23A	0.098 (4)	0.094 (3)	0.100 (3)	0.0024 (19)	−0.0061 (19)	0.0016 (19)

Geometric parameters (Å, º)

O1—C6	1.409 (3)	C13—H13B	0.9600
O1—C17	1.356 (3)	C13—H13C	0.9600
O2—C17	1.183 (3)	C14—H14	0.9800
O3—C21	1.234 (3)	C14—C15	1.520 (4)
O4—C21	1.264 (3)	C14—C16	1.510 (4)
N1—C1	1.360 (4)	C15—H15A	0.9600
N1—C2	1.359 (3)	C15—H15B	0.9600
N1—H1	0.853 (10)	C15—H15C	0.9600
N2—C10	1.505 (3)	C16—H16A	0.9600
N2—C11	1.521 (4)	C16—H16B	0.9600
N2—C14	1.517 (3)	C16—H16C	0.9600
N2—H2	0.90 (3)	C17—C18	1.493 (3)
C1—H1A	0.9300	C18—H18A	0.9700
C1—C8	1.359 (3)	C18—H18B	0.9700
C2—C3	1.386 (4)	C18—C19	1.509 (3)
C2—C7	1.420 (3)	C19—H19A	0.9700
C3—H3	0.9300	C19—H19B	0.9700
C3—C4	1.370 (4)	C19—C20	1.498 (3)
C4—H4	0.9300	C20—H20A	0.9700
C4—C5	1.400 (4)	C20—H20B	0.9700
C5—H5	0.9300	C20—C21	1.518 (4)
C5—C6	1.358 (4)	O5—H5A	0.8200
C6—C7	1.397 (3)	O5—C22	1.439 (8)
C7—C8	1.427 (4)	C22—H22A	0.9700
C8—C9	1.499 (3)	C22—H22B	0.9700
C9—H9A	0.9700	C22—C23	1.496 (8)
C9—H9B	0.9700	C23—H23A	0.9600
C9—C10	1.521 (3)	C23—H23B	0.9600
C10—H10A	0.9700	C23—H23C	0.9600
C10—H10B	0.9700	O5A—H5AA	0.8200
C11—H11	0.9800	O5A—C22A	1.420 (8)
C11—C12	1.517 (4)	C22A—H22C	0.9700
C11—C13	1.514 (5)	C22A—H22D	0.9700
C12—H12A	0.9600	C22A—C23A	1.470 (8)
C12—H12B	0.9600	C23A—H23D	0.9600
C12—H12C	0.9600	C23A—H23E	0.9600
C13—H13A	0.9600	C23A—H23F	0.9600
C17—O1—C6	116.79 (18)	C15—C14—H14	107.3
C1—N1—H1	124 (2)	C16—C14—N2	110.5 (2)
C2—N1—C1	109.1 (2)	C16—C14—H14	107.3
C2—N1—H1	127 (2)	C16—C14—C15	112.3 (3)
C10—N2—C11	111.28 (19)	C14—C15—H15A	109.5
C10—N2—C14	112.0 (2)	C14—C15—H15B	109.5
C10—N2—H2	106.1 (17)	C14—C15—H15C	109.5
C11—N2—H2	107.4 (18)	H15A—C15—H15B	109.5
C14—N2—C11	113.6 (2)	H15A—C15—H15C	109.5
C14—N2—H2	106.0 (17)	H15B—C15—H15C	109.5
N1—C1—H1A	124.5	C14—C16—H16A	109.5
C8—C1—N1	111.1 (3)	C14—C16—H16B	109.5
C8—C1—H1A	124.5	C14—C16—H16C	109.5
N1—C2—C3	131.0 (2)	H16A—C16—H16B	109.5
N1—C2—C7	106.9 (2)	H16A—C16—H16C	109.5
C3—C2—C7	122.1 (2)	H16B—C16—H16C	109.5
C2—C3—H3	120.9	O1—C17—C18	111.0 (2)
C4—C3—C2	118.1 (2)	O2—C17—O1	122.7 (2)
C4—C3—H3	120.9	O2—C17—C18	126.3 (2)
C3—C4—H4	119.3	C17—C18—H18A	108.9
C3—C4—C5	121.3 (3)	C17—C18—H18B	108.9
C5—C4—H4	119.3	C17—C18—C19	113.5 (2)
C4—C5—H5	120.0	H18A—C18—H18B	107.7
C6—C5—C4	120.0 (3)	C19—C18—H18A	108.9
C6—C5—H5	120.0	C19—C18—H18B	108.9
C5—C6—O1	120.4 (2)	C18—C19—H19A	109.0
C5—C6—C7	121.4 (2)	C18—C19—H19B	109.0
C7—C6—O1	118.2 (2)	H19A—C19—H19B	107.8
C2—C7—C8	107.4 (2)	C20—C19—C18	113.1 (2)
C6—C7—C2	117.0 (2)	C20—C19—H19A	109.0
C6—C7—C8	135.6 (2)	C20—C19—H19B	109.0
C1—C8—C7	105.6 (2)	C19—C20—H20A	108.4
C1—C8—C9	124.9 (2)	C19—C20—H20B	108.4
C7—C8—C9	128.8 (2)	C19—C20—C21	115.7 (2)
C8—C9—H9A	110.0	H20A—C20—H20B	107.4
C8—C9—H9B	110.0	C21—C20—H20A	108.4
C8—C9—C10	108.65 (19)	C21—C20—H20B	108.4
H9A—C9—H9B	108.3	O3—C21—O4	122.7 (2)
C10—C9—H9A	110.0	O3—C21—C20	121.0 (2)
C10—C9—H9B	110.0	O4—C21—C20	116.3 (2)
N2—C10—C9	114.35 (19)	C22—O5—H5A	109.5
N2—C10—H10A	108.7	O5—C22—H22A	110.0
N2—C10—H10B	108.7	O5—C22—H22B	110.0
C9—C10—H10A	108.7	O5—C22—C23	108.4 (8)
C9—C10—H10B	108.7	H22A—C22—H22B	108.4
H10A—C10—H10B	107.6	C23—C22—H22A	110.0
N2—C11—H11	108.1	C23—C22—H22B	110.0
C12—C11—N2	111.6 (2)	C22—C23—H23A	109.5
C12—C11—H11	108.1	C22—C23—H23B	109.5
C13—C11—N2	110.0 (2)	C22—C23—H23C	109.5
C13—C11—H11	108.1	H23A—C23—H23B	109.5
C13—C11—C12	111.0 (3)	H23A—C23—H23C	109.5
C11—C12—H12A	109.5	H23B—C23—H23C	109.5
C11—C12—H12B	109.5	C22A—O5A—H5AA	109.5
C11—C12—H12C	109.5	O5A—C22A—H22C	111.4
H12A—C12—H12B	109.5	O5A—C22A—H22D	111.4
H12A—C12—H12C	109.5	O5A—C22A—C23A	101.9 (7)
H12B—C12—H12C	109.5	H22C—C22A—H22D	109.3
C11—C13—H13A	109.5	C23A—C22A—H22C	111.4
C11—C13—H13B	109.5	C23A—C22A—H22D	111.4
C11—C13—H13C	109.5	C22A—C23A—H23D	109.5
H13A—C13—H13B	109.5	C22A—C23A—H23E	109.5
H13A—C13—H13C	109.5	C22A—C23A—H23F	109.5
H13B—C13—H13C	109.5	H23D—C23A—H23E	109.5
N2—C14—H14	107.3	H23D—C23A—H23F	109.5
N2—C14—C15	111.9 (2)	H23E—C23A—H23F	109.5
O1—C6—C7—C2	179.04 (19)	C6—O1—C17—O2	0.6 (4)
O1—C6—C7—C8	0.8 (4)	C6—O1—C17—C18	−178.4 (2)
O1—C17—C18—C19	−176.7 (2)	C6—C7—C8—C1	179.0 (3)
O2—C17—C18—C19	4.3 (5)	C6—C7—C8—C9	8.9 (4)
N1—C1—C8—C7	0.0 (3)	C7—C2—C3—C4	−0.1 (4)
N1—C1—C8—C9	170.6 (2)	C7—C8—C9—C10	86.1 (3)
N1—C2—C3—C4	178.3 (3)	C8—C9—C10—N2	180.0 (2)
N1—C2—C7—C6	−179.8 (2)	C10—N2—C11—C12	−178.7 (3)
N1—C2—C7—C8	−1.1 (3)	C10—N2—C11—C13	57.7 (3)
C1—N1—C2—C3	−177.5 (3)	C10—N2—C14—C15	62.8 (3)
C1—N1—C2—C7	1.1 (3)	C10—N2—C14—C16	−63.1 (3)
C1—C8—C9—C10	−82.3 (3)	C11—N2—C10—C9	−105.4 (3)
C2—N1—C1—C8	−0.7 (3)	C11—N2—C14—C15	−64.3 (3)
C2—C3—C4—C5	1.0 (4)	C11—N2—C14—C16	169.8 (2)
C2—C7—C8—C1	0.7 (3)	C14—N2—C10—C9	126.3 (2)
C2—C7—C8—C9	−169.4 (2)	C14—N2—C11—C12	−51.2 (3)
C3—C2—C7—C6	−1.0 (3)	C14—N2—C11—C13	−174.8 (2)
C3—C2—C7—C8	177.7 (2)	C17—O1—C6—C5	−87.0 (3)
C3—C4—C5—C6	−0.8 (4)	C17—O1—C6—C7	95.2 (3)
C4—C5—C6—O1	−178.1 (2)	C17—C18—C19—C20	176.7 (3)
C4—C5—C6—C7	−0.4 (4)	C18—C19—C20—C21	172.6 (3)
C5—C6—C7—C2	1.2 (3)	C19—C20—C21—O3	−5.6 (5)
C5—C6—C7—C8	−177.0 (3)	C19—C20—C21—O4	175.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4^i	0.90 (3)	1.79 (3)	2.686 (3)	177 (3)
N1—H1···O3^ii	0.85 (1)	1.91 (1)	2.751 (3)	167 (3)
O5—H5A···O4^iii	0.82	1.97	2.692 (10)	147
O5A—H5AA···O4^iii	0.82	1.95	2.732 (6)	160

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