Norpsilocin: freebase and fumarate salt

The solid-state structure of the `magic mushroom' natural product norpsilocin is reported, as well as the synthesis and structure of its fumarate salt.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.038
• wR factor = 0.105
• Data-to-parameter ratio = 11.4

Structure: II

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.098
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level A
PLAT417_ALERT_2_A Short Inter D-H..H-D       H1       ..H2'      .       1.08 Ang.
                                                1-x,1-y,1-z  =      3_666 Check

Alert level C
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H5       ..H11D     .       2.12 Ang.
                                           1+x,3/2-y,-1/2+z  =      4_675 Check
PLAT420_ALERT_2_C D-H Without Acceptor       N2       --H2       .     Please Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         12 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          9 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         14 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          7 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          2 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          3 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          2 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        29% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        105 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         11 Note
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Info

   1 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
  16 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
   5 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.865 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          7 Note
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.004 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
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
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         15 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          5 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For both 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).

3-[2-(Methylamino)ethyl]-1H-indol-4-ol (I)

Crystal data

C11H14N2O	F(000) = 408
Mr = 190.24	Dx = 1.273 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.4060 (16) Å	Cell parameters from 9944 reflections
b = 8.8436 (15) Å	θ = 2.9–26.0°
c = 12.144 (2) Å	µ = 0.08 mm^−1
β = 100.601 (7)°	T = 297 K
V = 993.0 (3) Å^3	BLOCK, colourless
Z = 4	0.35 × 0.2 × 0.1 mm

Data collection

Bruker D8 Venture CMOS diffractometer	1687 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.031
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θmax = 26.1°, θmin = 3.2°
Tmin = 0.716, Tmax = 0.745	h = −11→11
35681 measured reflections	k = −10→10
1955 independent reflections	l = −14→15

Refinement

Refinement on F^2	105 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 0.2586P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1955 reflections	Δρmax = 0.20 e Å^−3
171 parameters	Δρmin = −0.14 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	0.72180 (10)	0.50889 (10)	0.48264 (7)	0.0392 (3)
H1	0.7503 (17)	0.4189 (12)	0.5019 (14)	0.059*
N1	0.67378 (13)	0.84618 (14)	0.18771 (10)	0.0460 (3)
H1A	0.6832 (18)	0.8918 (18)	0.1255 (10)	0.055*
C1	0.70586 (13)	0.68167 (13)	0.33046 (10)	0.0311 (3)
C2	0.77773 (13)	0.56216 (13)	0.39398 (9)	0.0313 (3)
C3	0.90077 (14)	0.50210 (15)	0.36388 (11)	0.0387 (3)
H3	0.949534	0.424117	0.406353	0.046*
C4	0.95365 (15)	0.55642 (17)	0.27050 (12)	0.0451 (3)
H4	1.036369	0.513198	0.252150	0.054*
C5	0.88612 (15)	0.67154 (16)	0.20592 (12)	0.0441 (3)
H5	0.920870	0.707054	0.143824	0.053*
C6	0.76258 (14)	0.73365 (14)	0.23720 (10)	0.0364 (3)
C7	0.56146 (15)	0.86403 (16)	0.24481 (12)	0.0440 (3)
H7	0.486086	0.932698	0.225640	0.053*
C8	0.57603 (14)	0.76694 (14)	0.33354 (11)	0.0356 (3)
C9	0.4767 (3)	0.7551 (3)	0.4179 (3)	0.0401 (6)	0.895 (3)
H9A	0.512632	0.820479	0.481067	0.048*	0.895 (3)
H9B	0.478389	0.652079	0.445479	0.048*	0.895 (3)
C10	0.32164 (18)	0.7988 (2)	0.36920 (16)	0.0426 (4)	0.895 (3)
H10A	0.318567	0.904813	0.348540	0.051*	0.895 (3)
H10B	0.288874	0.740378	0.301680	0.051*	0.895 (3)
N2	0.22260 (16)	0.77279 (16)	0.44818 (14)	0.0414 (4)	0.895 (3)
H2	0.1338 (10)	0.778 (2)	0.4114 (8)	0.050*	0.895 (3)
C11	0.2400 (3)	0.8822 (2)	0.54022 (17)	0.0644 (6)	0.895 (3)
H11A	0.233857	0.982920	0.510261	0.097*	0.895 (3)
H11B	0.332532	0.867982	0.587682	0.097*	0.895 (3)
H11C	0.164866	0.867360	0.583032	0.097*	0.895 (3)
C9'	0.477 (3)	0.724 (3)	0.410 (3)	0.0401 (6)	0.105 (3)
H9'A	0.533638	0.706474	0.484119	0.048*	0.105 (3)
H9'B	0.430684	0.628565	0.384330	0.048*	0.105 (3)
C10'	0.3608 (18)	0.8382 (19)	0.4191 (15)	0.050 (2)	0.105 (3)
H10C	0.405248	0.936642	0.435346	0.060*	0.105 (3)
H10D	0.294887	0.844927	0.347824	0.060*	0.105 (3)
N2'	0.2784 (14)	0.7990 (17)	0.5074 (13)	0.053 (3)	0.105 (3)
H2'	0.256 (4)	0.703 (2)	0.500 (4)	0.063*	0.105 (3)
C11'	0.143 (2)	0.884 (3)	0.507 (2)	0.083 (6)	0.105 (3)
H11D	0.098734	0.849865	0.567605	0.125*	0.105 (3)
H11E	0.165025	0.990058	0.516272	0.125*	0.105 (3)
H11F	0.078492	0.868185	0.437255	0.125*	0.105 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0534 (6)	0.0345 (5)	0.0337 (5)	0.0108 (4)	0.0185 (4)	0.0063 (4)
N1	0.0523 (7)	0.0466 (7)	0.0415 (6)	0.0002 (5)	0.0151 (5)	0.0174 (5)
C1	0.0332 (6)	0.0300 (6)	0.0311 (6)	−0.0049 (5)	0.0081 (5)	−0.0009 (4)
C2	0.0354 (6)	0.0311 (6)	0.0279 (6)	−0.0023 (5)	0.0074 (4)	−0.0021 (4)
C3	0.0362 (7)	0.0393 (7)	0.0407 (7)	0.0042 (5)	0.0074 (5)	0.0000 (5)
C4	0.0368 (7)	0.0494 (8)	0.0536 (8)	−0.0024 (6)	0.0199 (6)	−0.0049 (6)
C5	0.0448 (7)	0.0475 (8)	0.0451 (7)	−0.0096 (6)	0.0218 (6)	0.0017 (6)
C6	0.0385 (7)	0.0359 (6)	0.0357 (6)	−0.0072 (5)	0.0097 (5)	0.0025 (5)
C7	0.0448 (7)	0.0419 (7)	0.0463 (7)	0.0058 (6)	0.0109 (6)	0.0132 (6)
C8	0.0372 (6)	0.0334 (6)	0.0374 (6)	0.0012 (5)	0.0097 (5)	0.0051 (5)
C9	0.0448 (7)	0.0372 (15)	0.0414 (10)	0.0089 (9)	0.0160 (6)	0.0076 (10)
C10	0.0412 (9)	0.0473 (10)	0.0411 (9)	0.0100 (7)	0.0124 (7)	0.0124 (7)
N2	0.0383 (7)	0.0431 (8)	0.0450 (8)	0.0085 (6)	0.0132 (6)	0.0071 (6)
C11	0.0799 (15)	0.0521 (11)	0.0699 (13)	0.0053 (11)	0.0368 (11)	−0.0077 (10)
C9'	0.0448 (7)	0.0372 (15)	0.0414 (10)	0.0089 (9)	0.0160 (6)	0.0076 (10)
C10'	0.053 (5)	0.046 (4)	0.053 (5)	0.007 (4)	0.015 (4)	0.005 (4)
N2'	0.059 (5)	0.046 (5)	0.059 (6)	0.007 (5)	0.026 (5)	0.001 (5)
C11'	0.066 (10)	0.078 (11)	0.112 (13)	0.024 (9)	0.038 (9)	0.027 (10)

Geometric parameters (Å, º)

O1—H1	0.858 (9)	C9—C10	1.520 (3)
O1—C2	1.3662 (14)	C10—H10A	0.9700
N1—H1A	0.875 (9)	C10—H10B	0.9700
N1—C6	1.3655 (18)	C10—N2	1.4729 (19)
N1—C7	1.3753 (18)	N2—H2	0.873 (9)
C1—C2	1.4061 (17)	N2—C11	1.464 (2)
C1—C6	1.4147 (17)	C11—H11A	0.9600
C1—C8	1.4416 (17)	C11—H11B	0.9600
C2—C3	1.3823 (18)	C11—H11C	0.9600
C3—H3	0.9300	C9'—H9'A	0.9700
C3—C4	1.4042 (19)	C9'—H9'B	0.9700
C4—H4	0.9300	C9'—C10'	1.509 (10)
C4—C5	1.368 (2)	C10'—H10C	0.9700
C5—H5	0.9300	C10'—H10D	0.9700
C5—C6	1.3995 (19)	C10'—N2'	1.476 (9)
C7—H7	0.9300	N2'—H2'	0.876 (14)
C7—C8	1.3649 (18)	N2'—C11'	1.476 (10)
C8—C9	1.512 (3)	C11'—H11D	0.9600
C8—C9'	1.48 (3)	C11'—H11E	0.9600
C9—H9A	0.9700	C11'—H11F	0.9600
C9—H9B	0.9700
C2—O1—H1	112.8 (11)	C9—C10—H10A	109.1
C6—N1—H1A	124.4 (12)	C9—C10—H10B	109.1
C6—N1—C7	109.04 (11)	H10A—C10—H10B	107.8
C7—N1—H1A	126.3 (11)	N2—C10—C9	112.57 (17)
C2—C1—C6	118.00 (11)	N2—C10—H10A	109.1
C2—C1—C8	134.67 (11)	N2—C10—H10B	109.1
C6—C1—C8	107.27 (11)	C10—N2—H2	108.6 (7)
O1—C2—C1	118.40 (10)	C11—N2—C10	113.51 (15)
O1—C2—C3	122.57 (11)	C11—N2—H2	108.6 (7)
C3—C2—C1	119.03 (11)	N2—C11—H11A	109.5
C2—C3—H3	119.3	N2—C11—H11B	109.5
C2—C3—C4	121.35 (13)	N2—C11—H11C	109.5
C4—C3—H3	119.3	H11A—C11—H11B	109.5
C3—C4—H4	119.3	H11A—C11—H11C	109.5
C5—C4—C3	121.43 (13)	H11B—C11—H11C	109.5
C5—C4—H4	119.3	C8—C9'—H9'A	108.6
C4—C5—H5	121.4	C8—C9'—H9'B	108.6
C4—C5—C6	117.23 (12)	C8—C9'—C10'	115 (2)
C6—C5—H5	121.4	H9'A—C9'—H9'B	107.6
N1—C6—C1	107.40 (11)	C10'—C9'—H9'A	108.6
N1—C6—C5	129.63 (12)	C10'—C9'—H9'B	108.6
C5—C6—C1	122.96 (12)	C9'—C10'—H10C	109.1
N1—C7—H7	124.7	C9'—C10'—H10D	109.1
C8—C7—N1	110.55 (12)	H10C—C10'—H10D	107.9
C8—C7—H7	124.7	N2'—C10'—C9'	112.3 (16)
C1—C8—C9	127.83 (14)	N2'—C10'—H10C	109.1
C1—C8—C9'	120.9 (8)	N2'—C10'—H10D	109.1
C7—C8—C1	105.73 (11)	C10'—N2'—H2'	107.7 (14)
C7—C8—C9	126.43 (15)	C10'—N2'—C11'	116.4 (13)
C7—C8—C9'	132.4 (9)	C11'—N2'—H2'	107.6 (14)
C8—C9—H9A	109.0	N2'—C11'—H11D	109.5
C8—C9—H9B	109.0	N2'—C11'—H11E	109.5
C8—C9—C10	112.8 (2)	N2'—C11'—H11F	109.5
H9A—C9—H9B	107.8	H11D—C11'—H11E	109.5
C10—C9—H9A	109.0	H11D—C11'—H11F	109.5
C10—C9—H9B	109.0	H11E—C11'—H11F	109.5
O1—C2—C3—C4	178.26 (11)	C6—C1—C2—O1	−178.50 (10)
N1—C7—C8—C1	−0.66 (16)	C6—C1—C2—C3	0.80 (17)
N1—C7—C8—C9	178.33 (19)	C6—C1—C8—C7	−0.28 (14)
N1—C7—C8—C9'	−169 (2)	C6—C1—C8—C9	−179.24 (18)
C1—C2—C3—C4	−1.01 (19)	C6—C1—C8—C9'	169.9 (18)
C1—C8—C9—C10	−151.89 (16)	C7—N1—C6—C1	−1.52 (15)
C1—C8—C9'—C10'	169.5 (18)	C7—N1—C6—C5	176.94 (14)
C2—C1—C6—N1	178.58 (11)	C7—C8—C9—C10	29.3 (3)
C2—C1—C6—C5	−0.01 (19)	C7—C8—C9'—C10'	−23 (4)
C2—C1—C8—C7	−177.14 (14)	C8—C1—C2—O1	−1.9 (2)
C2—C1—C8—C9	3.9 (3)	C8—C1—C2—C3	177.41 (13)
C2—C1—C8—C9'	−7.0 (18)	C8—C1—C6—N1	1.11 (14)
C2—C3—C4—C5	0.4 (2)	C8—C1—C6—C5	−177.48 (12)
C3—C4—C5—C6	0.4 (2)	C8—C9—C10—N2	174.34 (15)
C4—C5—C6—N1	−178.84 (14)	C8—C9'—C10'—N2'	−172 (2)
C4—C5—C6—C1	−0.6 (2)	C9—C10—N2—C11	73.1 (2)
C6—N1—C7—C8	1.39 (17)	C9'—C10'—N2'—C11'	−167 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2^i	0.86 (1)	1.80 (1)	2.6501 (16)	169 (2)
N1—H1A···O1^ii	0.88 (1)	2.04 (1)	2.9092 (15)	175 (2)

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

Bis{[2-(4-hydroxy-1H-indol-3-yl)ethyl]methylazanium} but-2-enedioate (II)

Crystal data

C11H15N2O^+·0.5C4H2O4^2^−	Z = 2
Mr = 248.28	F(000) = 264
Triclinic, P1	Dx = 1.281 Mg m^−3
a = 7.7363 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7146 (12) Å	Cell parameters from 3848 reflections
c = 9.7854 (13) Å	θ = 2.7–25.5°
α = 105.524 (4)°	µ = 0.09 mm^−1
β = 110.554 (4)°	T = 297 K
γ = 97.167 (4)°	BLOCK, colourless
V = 643.69 (14) Å^3	0.24 × 0.19 × 0.03 mm

Data collection

Bruker D8 Venture CMOS diffractometer	1774 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.046
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θmax = 25.5°, θmin = 2.7°
Tmin = 0.685, Tmax = 0.745	h = −9→9
14395 measured reflections	k = −11→11
2365 independent reflections	l = −11→11

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)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0428P)^2 + 0.1031P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.098	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.15 e Å^−3
2365 reflections	Δρmin = −0.15 e Å^−3
181 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
4 restraints	Extinction coefficient: 0.035 (8)

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	0.71021 (18)	0.24171 (13)	0.73074 (16)	0.0516 (4)
N1	1.1025 (2)	0.68290 (16)	0.82025 (18)	0.0458 (4)
N2	1.1755 (2)	0.13836 (16)	0.45820 (17)	0.0390 (4)
C1	0.9034 (2)	0.47406 (17)	0.77976 (18)	0.0351 (4)
C2	0.7537 (2)	0.39203 (18)	0.79685 (19)	0.0391 (4)
C3	0.6597 (3)	0.4650 (2)	0.8775 (2)	0.0492 (5)
H3	0.559823	0.411333	0.888131	0.059*
C4	0.7117 (3)	0.6188 (2)	0.9441 (2)	0.0532 (5)
H4	0.644580	0.664964	0.997328	0.064*
C5	0.8583 (3)	0.7030 (2)	0.9328 (2)	0.0480 (5)
H5	0.893452	0.804937	0.978251	0.058*
C6	0.9524 (2)	0.62851 (18)	0.85004 (19)	0.0391 (4)
C7	1.1455 (3)	0.56779 (19)	0.7313 (2)	0.0444 (4)
H7	1.240746	0.577663	0.694858	0.053*
C8	1.0291 (2)	0.43736 (18)	0.70422 (19)	0.0379 (4)
C9	1.0327 (3)	0.28658 (18)	0.6159 (2)	0.0434 (4)
H9A	0.906459	0.236367	0.536418	0.052*
H9B	1.066169	0.230581	0.685761	0.052*
C10	1.1729 (2)	0.29082 (18)	0.5407 (2)	0.0398 (4)
H10A	1.137504	0.343594	0.467796	0.048*
H10B	1.299028	0.342809	0.619295	0.048*
C11	1.3055 (3)	0.1317 (2)	0.3774 (2)	0.0561 (5)
H11A	1.293563	0.030805	0.321818	0.084*
H11B	1.434183	0.174879	0.451983	0.084*
H11C	1.273049	0.184976	0.306086	0.084*
C12	0.3434 (2)	0.02114 (16)	0.80503 (17)	0.0311 (4)
C13	0.5073 (2)	0.01566 (17)	0.94080 (18)	0.0344 (4)
H13	0.628166	0.035974	0.941097	0.041*
O2	0.17836 (15)	−0.03196 (13)	0.78734 (13)	0.0423 (3)
O3	0.38449 (16)	0.07932 (13)	0.71675 (14)	0.0461 (3)
H1	0.613 (2)	0.203 (2)	0.745 (3)	0.074 (7)*
H1A	1.141 (3)	0.7760 (12)	0.839 (2)	0.069 (7)*
H2A	1.216 (3)	0.0955 (19)	0.5298 (18)	0.054 (6)*
H2B	1.0586 (16)	0.0926 (19)	0.3889 (18)	0.054 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0481 (8)	0.0429 (7)	0.0624 (9)	−0.0009 (6)	0.0278 (7)	0.0135 (6)
N1	0.0510 (9)	0.0347 (8)	0.0500 (9)	0.0033 (7)	0.0194 (8)	0.0161 (7)
N2	0.0369 (8)	0.0476 (9)	0.0337 (8)	0.0135 (7)	0.0111 (7)	0.0178 (7)
C1	0.0342 (9)	0.0385 (9)	0.0306 (9)	0.0070 (7)	0.0094 (7)	0.0145 (7)
C2	0.0376 (9)	0.0407 (9)	0.0353 (9)	0.0049 (7)	0.0115 (8)	0.0133 (7)
C3	0.0429 (10)	0.0626 (12)	0.0477 (11)	0.0107 (9)	0.0233 (9)	0.0212 (9)
C4	0.0609 (12)	0.0589 (12)	0.0486 (12)	0.0230 (10)	0.0304 (10)	0.0167 (9)
C5	0.0625 (12)	0.0408 (10)	0.0409 (10)	0.0169 (9)	0.0199 (9)	0.0130 (8)
C6	0.0419 (9)	0.0393 (9)	0.0348 (9)	0.0079 (7)	0.0114 (8)	0.0166 (7)
C7	0.0433 (10)	0.0475 (10)	0.0468 (11)	0.0067 (8)	0.0217 (9)	0.0199 (8)
C8	0.0369 (9)	0.0417 (9)	0.0363 (9)	0.0085 (7)	0.0139 (8)	0.0162 (7)
C9	0.0430 (10)	0.0425 (10)	0.0457 (10)	0.0084 (8)	0.0201 (9)	0.0144 (8)
C10	0.0387 (9)	0.0421 (9)	0.0389 (10)	0.0102 (7)	0.0132 (8)	0.0170 (7)
C11	0.0576 (12)	0.0740 (14)	0.0527 (12)	0.0281 (10)	0.0307 (10)	0.0291 (10)
C12	0.0330 (9)	0.0272 (8)	0.0294 (8)	0.0041 (6)	0.0086 (7)	0.0106 (6)
C13	0.0287 (8)	0.0385 (9)	0.0343 (9)	0.0043 (7)	0.0097 (7)	0.0154 (7)
O2	0.0297 (6)	0.0494 (7)	0.0429 (7)	0.0014 (5)	0.0060 (5)	0.0233 (6)
O3	0.0399 (7)	0.0606 (8)	0.0412 (7)	0.0057 (6)	0.0114 (6)	0.0322 (6)

Geometric parameters (Å, º)

O1—C2	1.372 (2)	C5—C6	1.393 (3)
O1—H1	0.870 (10)	C7—H7	0.9300
N1—C6	1.372 (2)	C7—C8	1.362 (2)
N1—C7	1.376 (2)	C8—C9	1.498 (2)
N1—H1A	0.863 (10)	C9—H9A	0.9700
N2—C10	1.492 (2)	C9—H9B	0.9700
N2—C11	1.479 (2)	C9—C10	1.511 (2)
N2—H2A	0.892 (9)	C10—H10A	0.9700
N2—H2B	0.885 (9)	C10—H10B	0.9700
C1—C2	1.408 (2)	C11—H11A	0.9600
C1—C6	1.411 (2)	C11—H11B	0.9600
C1—C8	1.438 (2)	C11—H11C	0.9600
C2—C3	1.373 (3)	C12—C13	1.499 (2)
C3—H3	0.9300	C12—O2	1.2488 (18)
C3—C4	1.402 (3)	C12—O3	1.2553 (18)
C4—H4	0.9300	C13—C13^i	1.311 (3)
C4—C5	1.368 (3)	C13—H13	0.9300
C5—H5	0.9300
C2—O1—H1	109.6 (15)	C8—C7—N1	110.51 (15)
C6—N1—C7	108.98 (14)	C8—C7—H7	124.7
C6—N1—H1A	121.5 (15)	C1—C8—C9	127.04 (14)
C7—N1—H1A	128.2 (15)	C7—C8—C1	105.81 (15)
C10—N2—H2A	106.9 (13)	C7—C8—C9	127.14 (16)
C10—N2—H2B	107.9 (13)	C8—C9—H9A	109.1
C11—N2—C10	114.20 (14)	C8—C9—H9B	109.1
C11—N2—H2A	107.5 (13)	C8—C9—C10	112.38 (13)
C11—N2—H2B	108.4 (13)	H9A—C9—H9B	107.9
H2A—N2—H2B	112.1 (18)	C10—C9—H9A	109.1
C2—C1—C6	117.87 (15)	C10—C9—H9B	109.1
C2—C1—C8	134.53 (15)	N2—C10—C9	110.39 (13)
C6—C1—C8	107.60 (14)	N2—C10—H10A	109.6
O1—C2—C1	117.25 (15)	N2—C10—H10B	109.6
O1—C2—C3	123.67 (15)	C9—C10—H10A	109.6
C3—C2—C1	119.08 (16)	C9—C10—H10B	109.6
C2—C3—H3	119.4	H10A—C10—H10B	108.1
C2—C3—C4	121.20 (17)	N2—C11—H11A	109.5
C4—C3—H3	119.4	N2—C11—H11B	109.5
C3—C4—H4	119.1	N2—C11—H11C	109.5
C5—C4—C3	121.82 (18)	H11A—C11—H11B	109.5
C5—C4—H4	119.1	H11A—C11—H11C	109.5
C4—C5—H5	121.6	H11B—C11—H11C	109.5
C4—C5—C6	116.76 (17)	O2—C12—C13	118.55 (13)
C6—C5—H5	121.6	O2—C12—O3	124.96 (14)
N1—C6—C1	107.08 (15)	O3—C12—C13	116.49 (14)
N1—C6—C5	129.66 (16)	C12—C13—H13	117.6
C5—C6—C1	123.26 (16)	C13^i—C13—C12	124.77 (19)
N1—C7—H7	124.7	C13^i—C13—H13	117.6
O1—C2—C3—C4	179.30 (17)	C6—C1—C2—C3	1.4 (2)
N1—C7—C8—C1	0.79 (19)	C6—C1—C8—C7	−0.02 (18)
N1—C7—C8—C9	−178.45 (16)	C6—C1—C8—C9	179.22 (16)
C1—C2—C3—C4	−0.7 (3)	C7—N1—C6—C1	1.23 (18)
C1—C8—C9—C10	175.12 (15)	C7—N1—C6—C5	−179.00 (18)
C2—C1—C6—N1	178.79 (14)	C7—C8—C9—C10	−5.8 (3)
C2—C1—C6—C5	−1.0 (2)	C8—C1—C2—O1	0.7 (3)
C2—C1—C8—C7	−179.45 (18)	C8—C1—C2—C3	−179.26 (18)
C2—C1—C8—C9	−0.2 (3)	C8—C1—C6—N1	−0.74 (18)
C2—C3—C4—C5	−0.5 (3)	C8—C1—C6—C5	179.47 (16)
C3—C4—C5—C6	0.8 (3)	C8—C9—C10—N2	178.34 (14)
C4—C5—C6—N1	−179.84 (17)	C11—N2—C10—C9	178.49 (15)
C4—C5—C6—C1	−0.1 (3)	O2—C12—C13—C13^i	−13.3 (3)
C6—N1—C7—C8	−1.3 (2)	O3—C12—C13—C13^i	167.0 (2)
C6—C1—C2—O1	−178.63 (14)

Symmetry code: (i) −x+1, −y, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.87 (1)	1.89 (1)	2.7399 (16)	163 (2)
N1—H1A···O2^ii	0.86 (1)	2.07 (1)	2.8854 (18)	157 (2)
N2—H2A···O3^iii	0.89 (1)	1.90 (1)	2.7349 (18)	155 (2)
N2—H2B···O2^iv	0.89 (1)	1.91 (1)	2.7715 (19)	164 (2)

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