5-Meth­oxy-N,N-di-n-propyl­tryptamine (5-MeO-DPT): freebase and fumarate

The solid-state structure of the synthetic psychedelic 5-MeO-DPT is reported in its freebase form and as its fumarate salt.

Key indicators

Structure: umd2187e_a

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.117
• Data-to-parameter ratio = 16.1

Structure: umd2188f_a

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.052
• wR factor = 0.142
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Datablock: umd2187e_a



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C12 Check
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
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
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

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

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




Datablock: umd2188f_a



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         48 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         35 Note

Alert level G
PLAT042_ALERT_1_G Calc. and Reported Moiety Formula Strings Differ     Please Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
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          5 Note
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.          5 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
   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

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

N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-propylpropan-1-amine (umd2187e_a)

Crystal data

C17H26N2O	F(000) = 600
Mr = 274.40	Dx = 1.132 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.2223 (3) Å	Cell parameters from 9916 reflections
b = 13.0931 (6) Å	θ = 3.3–25.6°
c = 19.7791 (10) Å	µ = 0.07 mm^−1
β = 91.825 (2)°	T = 297 K
V = 1610.57 (13) Å^3	PLATE, colourless
Z = 4	0.38 × 0.3 × 0.06 mm

Data collection

Bruker D8 Venture CMOS diffractometer	2466 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.038
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θmax = 25.7°, θmin = 3.3°
Tmin = 0.687, Tmax = 0.745	h = −7→7
29365 measured reflections	k = −15→15
3035 independent reflections	l = −24→24

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)] = 0.042	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 0.3694P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.117	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.14 e Å^−3
3035 reflections	Δρmin = −0.17 e Å^−3
189 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.046 (13)

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	0.64844 (19)	0.70622 (10)	0.52927 (6)	0.0702 (4)
N1	0.9733 (2)	0.87177 (9)	0.29883 (7)	0.0504 (3)
N2	0.28056 (16)	0.56376 (8)	0.22986 (5)	0.0412 (3)
C1	0.8201 (2)	0.84119 (10)	0.25168 (8)	0.0494 (4)
H1A	0.821475	0.857658	0.205961	0.059*
C2	0.9167 (2)	0.83449 (10)	0.36067 (7)	0.0452 (3)
C3	1.0138 (2)	0.84559 (12)	0.42487 (8)	0.0569 (4)
H3	1.140767	0.882380	0.430949	0.068*
C4	0.9172 (3)	0.80093 (13)	0.47864 (8)	0.0597 (4)
H4	0.980435	0.807252	0.521685	0.072*
C5	0.7252 (2)	0.74592 (11)	0.47013 (8)	0.0523 (4)
C6	0.6272 (2)	0.73433 (10)	0.40727 (7)	0.0472 (4)
H6	0.499370	0.697976	0.401965	0.057*
C7	0.7248 (2)	0.77873 (9)	0.35118 (7)	0.0421 (3)
C8	0.6655 (2)	0.78344 (10)	0.28070 (7)	0.0442 (3)
C9	0.4698 (2)	0.73615 (10)	0.24763 (8)	0.0501 (4)
H9A	0.450938	0.763236	0.202185	0.060*
H9B	0.344490	0.755116	0.272754	0.060*
C10	0.4834 (2)	0.61913 (10)	0.24396 (7)	0.0429 (3)
H10A	0.583107	0.601344	0.209131	0.051*
H10B	0.544432	0.594539	0.286666	0.051*
C11	0.1721 (2)	0.60049 (11)	0.16734 (7)	0.0476 (4)
H11A	0.279545	0.613815	0.133983	0.057*
H11B	0.100723	0.664575	0.176709	0.057*
C12	0.0078 (2)	0.52602 (12)	0.13767 (8)	0.0530 (4)
H12A	0.080879	0.464283	0.124003	0.064*
H12B	−0.092372	0.507608	0.172213	0.064*
C13	−0.1154 (4)	0.56964 (18)	0.07758 (10)	0.0941 (7)
H13A	−0.216369	0.519855	0.060362	0.141*
H13B	−0.017190	0.587135	0.042962	0.141*
H13C	−0.191324	0.629728	0.091108	0.141*
C14	0.1352 (2)	0.56727 (12)	0.28718 (7)	0.0508 (4)
H14A	−0.007626	0.547160	0.271228	0.061*
H14B	0.126623	0.637215	0.303036	0.061*
C15	0.2017 (3)	0.50025 (12)	0.34569 (8)	0.0598 (4)
H15A	0.339619	0.523201	0.364219	0.072*
H15B	0.218942	0.430741	0.329783	0.072*
C16	0.0390 (3)	0.50174 (17)	0.40067 (10)	0.0814 (6)
H16A	0.084291	0.456110	0.436343	0.122*
H16B	−0.098413	0.480319	0.382311	0.122*
H16C	0.027543	0.569755	0.418335	0.122*
C17	0.4531 (3)	0.65147 (16)	0.52456 (10)	0.0800 (6)
H17A	0.414835	0.629014	0.568787	0.120*
H17B	0.469744	0.593254	0.495692	0.120*
H17C	0.341808	0.694924	0.505997	0.120*
H1	1.073 (3)	0.9177 (14)	0.2916 (9)	0.066 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0744 (8)	0.0789 (8)	0.0573 (7)	0.0026 (6)	0.0055 (6)	0.0104 (6)
N1	0.0454 (7)	0.0430 (7)	0.0630 (8)	−0.0051 (5)	0.0051 (6)	−0.0007 (6)
N2	0.0352 (5)	0.0404 (6)	0.0482 (6)	0.0007 (4)	0.0025 (4)	0.0014 (5)
C1	0.0542 (8)	0.0387 (7)	0.0554 (8)	0.0021 (6)	0.0036 (7)	−0.0006 (6)
C2	0.0399 (7)	0.0370 (7)	0.0587 (8)	0.0038 (5)	0.0017 (6)	−0.0042 (6)
C3	0.0425 (7)	0.0584 (9)	0.0691 (10)	−0.0016 (7)	−0.0065 (7)	−0.0082 (8)
C4	0.0540 (9)	0.0680 (10)	0.0564 (9)	0.0060 (8)	−0.0074 (7)	−0.0066 (8)
C5	0.0527 (8)	0.0495 (8)	0.0550 (9)	0.0098 (7)	0.0039 (7)	0.0013 (7)
C6	0.0435 (7)	0.0394 (7)	0.0587 (9)	0.0014 (6)	0.0013 (6)	0.0002 (6)
C7	0.0387 (7)	0.0320 (6)	0.0555 (8)	0.0045 (5)	0.0010 (6)	−0.0035 (6)
C8	0.0446 (7)	0.0319 (6)	0.0559 (8)	0.0032 (5)	−0.0008 (6)	−0.0030 (6)
C9	0.0487 (8)	0.0392 (7)	0.0616 (9)	0.0025 (6)	−0.0092 (6)	−0.0008 (6)
C10	0.0363 (7)	0.0395 (7)	0.0528 (8)	0.0019 (5)	0.0013 (5)	−0.0017 (6)
C11	0.0469 (7)	0.0464 (8)	0.0493 (8)	−0.0055 (6)	−0.0007 (6)	0.0040 (6)
C12	0.0456 (8)	0.0514 (8)	0.0617 (9)	−0.0052 (6)	−0.0030 (6)	0.0013 (7)
C13	0.0982 (15)	0.1021 (16)	0.0794 (13)	−0.0435 (13)	−0.0369 (11)	0.0253 (12)
C14	0.0422 (7)	0.0563 (9)	0.0543 (8)	0.0048 (6)	0.0060 (6)	0.0050 (7)
C15	0.0695 (10)	0.0524 (9)	0.0579 (9)	0.0011 (8)	0.0090 (7)	0.0071 (7)
C16	0.0866 (13)	0.0960 (15)	0.0627 (11)	−0.0025 (11)	0.0185 (9)	0.0148 (10)
C17	0.0822 (12)	0.0812 (13)	0.0773 (12)	−0.0058 (10)	0.0137 (10)	0.0226 (10)

Geometric parameters (Å, º)

O1—C5	1.3794 (18)	C10—H10A	0.9700
O1—C17	1.412 (2)	C10—H10B	0.9700
N1—C1	1.3716 (19)	C11—H11A	0.9700
N1—C2	1.3734 (19)	C11—H11B	0.9700
N1—H1	0.878 (18)	C11—C12	1.5171 (19)
N2—C10	1.4745 (16)	C12—H12A	0.9700
N2—C11	1.4705 (17)	C12—H12B	0.9700
N2—C14	1.4735 (17)	C12—C13	1.506 (2)
C1—H1A	0.9300	C13—H13A	0.9600
C1—C8	1.364 (2)	C13—H13B	0.9600
C2—C3	1.396 (2)	C13—H13C	0.9600
C2—C7	1.4070 (18)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C3—C4	1.369 (2)	C14—C15	1.500 (2)
C4—H4	0.9300	C15—H15A	0.9700
C4—C5	1.401 (2)	C15—H15B	0.9700
C5—C6	1.376 (2)	C15—C16	1.510 (2)
C6—H6	0.9300	C16—H16A	0.9600
C6—C7	1.4071 (19)	C16—H16B	0.9600
C7—C8	1.4318 (19)	C16—H16C	0.9600
C8—C9	1.4980 (19)	C17—H17A	0.9600
C9—H9A	0.9700	C17—H17B	0.9600
C9—H9B	0.9700	C17—H17C	0.9600
C9—C10	1.5363 (18)
C5—O1—C17	117.15 (13)	N2—C11—H11A	108.8
C1—N1—C2	108.02 (12)	N2—C11—H11B	108.8
C1—N1—H1	124.6 (11)	N2—C11—C12	113.62 (11)
C2—N1—H1	126.2 (11)	H11A—C11—H11B	107.7
C11—N2—C10	111.44 (10)	C12—C11—H11A	108.8
C11—N2—C14	111.12 (10)	C12—C11—H11B	108.8
C14—N2—C10	112.44 (11)	C11—C12—H12A	109.1
N1—C1—H1A	124.5	C11—C12—H12B	109.1
C8—C1—N1	111.08 (13)	H12A—C12—H12B	107.9
C8—C1—H1A	124.5	C13—C12—C11	112.43 (13)
N1—C2—C3	131.08 (13)	C13—C12—H12A	109.1
N1—C2—C7	107.83 (12)	C13—C12—H12B	109.1
C3—C2—C7	121.08 (14)	C12—C13—H13A	109.5
C2—C3—H3	120.8	C12—C13—H13B	109.5
C4—C3—C2	118.30 (14)	C12—C13—H13C	109.5
C4—C3—H3	120.8	H13A—C13—H13B	109.5
C3—C4—H4	119.3	H13A—C13—H13C	109.5
C3—C4—C5	121.32 (15)	H13B—C13—H13C	109.5
C5—C4—H4	119.3	N2—C14—H14A	108.6
O1—C5—C4	114.14 (14)	N2—C14—H14B	108.6
C6—C5—O1	124.69 (14)	N2—C14—C15	114.48 (12)
C6—C5—C4	121.16 (14)	H14A—C14—H14B	107.6
C5—C6—H6	120.8	C15—C14—H14A	108.6
C5—C6—C7	118.48 (13)	C15—C14—H14B	108.6
C7—C6—H6	120.8	C14—C15—H15A	109.2
C2—C7—C6	119.65 (13)	C14—C15—H15B	109.2
C2—C7—C8	107.37 (12)	C14—C15—C16	111.92 (14)
C6—C7—C8	132.94 (12)	H15A—C15—H15B	107.9
C1—C8—C7	105.68 (12)	C16—C15—H15A	109.2
C1—C8—C9	128.30 (14)	C16—C15—H15B	109.2
C7—C8—C9	126.00 (13)	C15—C16—H16A	109.5
C8—C9—H9A	109.0	C15—C16—H16B	109.5
C8—C9—H9B	109.0	C15—C16—H16C	109.5
C8—C9—C10	112.80 (11)	H16A—C16—H16B	109.5
H9A—C9—H9B	107.8	H16A—C16—H16C	109.5
C10—C9—H9A	109.0	H16B—C16—H16C	109.5
C10—C9—H9B	109.0	O1—C17—H17A	109.5
N2—C10—C9	116.81 (11)	O1—C17—H17B	109.5
N2—C10—H10A	108.1	O1—C17—H17C	109.5
N2—C10—H10B	108.1	H17A—C17—H17B	109.5
C9—C10—H10A	108.1	H17A—C17—H17C	109.5
C9—C10—H10B	108.1	H17B—C17—H17C	109.5
H10A—C10—H10B	107.3
O1—C5—C6—C7	−179.67 (13)	C3—C4—C5—C6	0.3 (2)
N1—C1—C8—C7	0.81 (15)	C4—C5—C6—C7	0.3 (2)
N1—C1—C8—C9	179.30 (13)	C5—C6—C7—C2	−0.84 (19)
N1—C2—C3—C4	178.54 (14)	C5—C6—C7—C8	−178.36 (13)
N1—C2—C7—C6	−178.18 (11)	C6—C7—C8—C1	177.31 (14)
N1—C2—C7—C8	−0.08 (14)	C6—C7—C8—C9	−1.2 (2)
N2—C11—C12—C13	174.55 (15)	C7—C2—C3—C4	−0.1 (2)
N2—C14—C15—C16	−176.15 (14)	C7—C8—C9—C10	−71.42 (18)
C1—N1—C2—C3	−178.24 (14)	C8—C9—C10—N2	163.85 (12)
C1—N1—C2—C7	0.57 (15)	C10—N2—C11—C12	160.69 (11)
C1—C8—C9—C10	110.38 (16)	C10—N2—C14—C15	−74.13 (16)
C2—N1—C1—C8	−0.88 (16)	C11—N2—C10—C9	55.06 (16)
C2—C3—C4—C5	−0.4 (2)	C11—N2—C14—C15	160.17 (13)
C2—C7—C8—C1	−0.44 (14)	C14—N2—C10—C9	−70.46 (15)
C2—C7—C8—C9	−178.97 (12)	C14—N2—C11—C12	−73.06 (15)
C3—C2—C7—C6	0.77 (19)	C17—O1—C5—C4	178.83 (15)
C3—C2—C7—C8	178.88 (12)	C17—O1—C5—C6	−1.2 (2)
C3—C4—C5—O1	−179.69 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2^i	0.878 (18)	2.167 (19)	3.0070 (17)	160.0 (16)

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

Bis{N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-propylpropan-1-aminium}; but-2-enedioate (umd2188f_a)

Crystal data

C17H27N2O^+·0.5C4H2O4^2^−	Z = 2
Mr = 332.43	F(000) = 360
Triclinic, P1	Dx = 1.171 Mg m^−3
a = 9.2956 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4443 (6) Å	Cell parameters from 9966 reflections
c = 12.7427 (8) Å	θ = 2.6–25.6°
α = 78.552 (2)°	µ = 0.08 mm^−1
β = 75.929 (2)°	T = 297 K
γ = 60.806 (2)°	BLOCK, colourless
V = 943.06 (11) Å^3	0.3 × 0.22 × 0.2 mm

Data collection

Bruker D8 Venture CMOS diffractometer	3006 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.032
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θmax = 25.8°, θmin = 2.6°
Tmin = 0.722, Tmax = 0.745	h = −11→11
37231 measured reflections	k = −11→11
3565 independent reflections	l = −15→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0652P)^2 + 0.3068P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3565 reflections	Δρmax = 0.29 e Å^−3
228 parameters	Δρmin = −0.15 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
O1	1.12338 (18)	0.1921 (2)	0.42565 (12)	0.0820 (5)
O3	0.56136 (18)	0.70109 (14)	0.91994 (11)	0.0619 (4)
O4	0.38521 (19)	0.94777 (15)	0.85790 (10)	0.0619 (4)
N1	0.6457 (2)	0.7968 (2)	0.29933 (12)	0.0592 (4)
N2	0.45383 (17)	0.62296 (15)	0.77576 (10)	0.0428 (3)
C1	0.5216 (3)	0.8238 (2)	0.38795 (14)	0.0569 (5)
H1A	0.419516	0.917793	0.395103	0.068*
C2	0.7767 (2)	0.6468 (2)	0.31704 (13)	0.0494 (4)
C3	0.9290 (3)	0.5609 (3)	0.25118 (14)	0.0611 (5)
H3	0.955315	0.605071	0.181743	0.073*
C4	1.0389 (2)	0.4104 (3)	0.29047 (15)	0.0635 (5)
H4	1.140948	0.351877	0.247161	0.076*
C5	1.0004 (2)	0.3427 (2)	0.39518 (15)	0.0564 (4)
C6	0.8487 (2)	0.4243 (2)	0.45998 (13)	0.0497 (4)
H6	0.822409	0.377642	0.528497	0.060*
C7	0.7346 (2)	0.5788 (2)	0.42102 (12)	0.0450 (4)
C8	0.5686 (2)	0.6934 (2)	0.46471 (13)	0.0474 (4)
C9	0.4679 (2)	0.6678 (2)	0.57159 (13)	0.0477 (4)
H9A	0.480231	0.558342	0.579746	0.057*
H9B	0.350672	0.743536	0.570911	0.057*
C10	0.5191 (2)	0.6913 (2)	0.66834 (12)	0.0470 (4)
H10A	0.640253	0.639174	0.658321	0.056*
H10B	0.478562	0.806815	0.670881	0.056*
C11	0.2669 (2)	0.7020 (2)	0.79912 (13)	0.0506 (4)
H11A	0.228284	0.658211	0.755537	0.061*
H11B	0.223555	0.817953	0.777702	0.061*
C12	0.1977 (3)	0.6766 (3)	0.91717 (16)	0.0767 (6)
H12A	0.232415	0.561287	0.936852	0.092*
H12B	0.244506	0.711049	0.961289	0.092*
C13	0.0122 (3)	0.7678 (4)	0.9418 (2)	0.1035 (10)
H13A	−0.026624	0.732314	1.013936	0.155*
H13B	−0.034648	0.747832	0.890459	0.155*
H13C	−0.021980	0.882313	0.937002	0.155*
C14	0.5291 (2)	0.44102 (19)	0.78992 (14)	0.0502 (4)
H14A	0.504193	0.405008	0.733484	0.060*
H14B	0.477479	0.408059	0.859428	0.060*
C15	0.7152 (2)	0.3582 (2)	0.78522 (16)	0.0616 (5)
H15A	0.740808	0.395586	0.840557	0.074*
H15B	0.767606	0.388253	0.714986	0.074*
C16	0.7866 (3)	0.1758 (3)	0.8025 (2)	0.0940 (8)
H16A	0.906071	0.127238	0.795009	0.141*
H16B	0.758181	0.138666	0.749425	0.141*
H16C	0.741153	0.145089	0.874057	0.141*
C17	1.1057 (3)	0.1353 (3)	0.5365 (2)	0.0943 (8)
H17A	1.209504	0.044150	0.551443	0.141*
H17B	1.019527	0.101981	0.553796	0.141*
H17C	1.076098	0.220867	0.579927	0.141*
C18	0.4904 (2)	0.85411 (19)	0.91702 (12)	0.0450 (4)
C19	0.5356 (2)	0.92260 (19)	0.99289 (13)	0.0459 (4)
H19	0.619664	0.850477	1.032462	0.055*
H2	0.488 (3)	0.653 (3)	0.8317 (18)	0.076 (6)*
H1	0.632 (3)	0.872 (3)	0.247 (2)	0.082 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0612 (9)	0.0809 (10)	0.0683 (9)	−0.0035 (7)	−0.0085 (7)	−0.0156 (8)
O3	0.0872 (9)	0.0419 (7)	0.0638 (8)	−0.0273 (6)	−0.0301 (7)	−0.0058 (5)
O4	0.0964 (10)	0.0497 (7)	0.0545 (7)	−0.0402 (7)	−0.0335 (7)	0.0072 (5)
N1	0.0791 (11)	0.0579 (9)	0.0412 (8)	−0.0367 (9)	−0.0112 (7)	0.0089 (7)
N2	0.0549 (8)	0.0428 (7)	0.0346 (6)	−0.0256 (6)	−0.0093 (6)	−0.0018 (5)
C1	0.0699 (12)	0.0494 (10)	0.0460 (9)	−0.0234 (9)	−0.0121 (8)	−0.0018 (7)
C2	0.0618 (10)	0.0595 (10)	0.0377 (8)	−0.0384 (9)	−0.0076 (7)	0.0000 (7)
C3	0.0678 (12)	0.0912 (15)	0.0387 (9)	−0.0523 (11)	0.0002 (8)	−0.0052 (9)
C4	0.0516 (10)	0.0923 (15)	0.0507 (10)	−0.0368 (11)	0.0031 (8)	−0.0204 (10)
C5	0.0494 (10)	0.0653 (11)	0.0528 (10)	−0.0225 (9)	−0.0094 (8)	−0.0125 (8)
C6	0.0530 (9)	0.0553 (10)	0.0389 (8)	−0.0253 (8)	−0.0057 (7)	−0.0027 (7)
C7	0.0528 (9)	0.0508 (9)	0.0366 (8)	−0.0290 (8)	−0.0062 (7)	−0.0034 (6)
C8	0.0589 (10)	0.0483 (9)	0.0382 (8)	−0.0269 (8)	−0.0091 (7)	−0.0039 (6)
C9	0.0522 (9)	0.0518 (9)	0.0401 (8)	−0.0246 (8)	−0.0066 (7)	−0.0069 (7)
C10	0.0602 (10)	0.0447 (8)	0.0402 (8)	−0.0278 (8)	−0.0094 (7)	−0.0021 (6)
C11	0.0560 (10)	0.0518 (9)	0.0417 (8)	−0.0234 (8)	−0.0094 (7)	−0.0020 (7)
C12	0.0666 (13)	0.0915 (16)	0.0490 (11)	−0.0273 (12)	−0.0023 (9)	0.0073 (10)
C13	0.0757 (16)	0.114 (2)	0.0622 (14)	−0.0133 (15)	0.0082 (12)	0.0053 (13)
C14	0.0616 (10)	0.0422 (9)	0.0496 (9)	−0.0266 (8)	−0.0120 (8)	0.0001 (7)
C15	0.0619 (11)	0.0588 (11)	0.0547 (10)	−0.0233 (9)	−0.0086 (8)	0.0003 (8)
C16	0.0797 (16)	0.0574 (13)	0.1040 (19)	−0.0150 (12)	0.0017 (14)	0.0112 (12)
C17	0.0861 (17)	0.0747 (15)	0.0759 (16)	0.0002 (13)	−0.0186 (13)	−0.0065 (12)
C18	0.0623 (10)	0.0445 (9)	0.0353 (7)	−0.0316 (8)	−0.0082 (7)	−0.0003 (6)
C19	0.0571 (10)	0.0450 (8)	0.0415 (8)	−0.0280 (7)	−0.0102 (7)	−0.0024 (6)

Geometric parameters (Å, º)

O1—C5	1.375 (2)	C10—H10A	0.9700
O1—C17	1.408 (3)	C10—H10B	0.9700
O3—C18	1.2592 (19)	C11—H11A	0.9700
O4—C18	1.247 (2)	C11—H11B	0.9700
N1—C1	1.365 (2)	C11—C12	1.507 (2)
N1—C2	1.365 (2)	C12—H12A	0.9700
N1—H1	0.86 (2)	C12—H12B	0.9700
N2—C10	1.512 (2)	C12—C13	1.486 (3)
N2—C11	1.496 (2)	C13—H13A	0.9600
N2—C14	1.497 (2)	C13—H13B	0.9600
N2—H2	0.98 (2)	C13—H13C	0.9600
C1—H1A	0.9300	C14—H14A	0.9700
C1—C8	1.367 (2)	C14—H14B	0.9700
C2—C3	1.392 (3)	C14—C15	1.503 (3)
C2—C7	1.406 (2)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C3—C4	1.365 (3)	C15—C16	1.504 (3)
C4—H4	0.9300	C16—H16A	0.9600
C4—C5	1.404 (3)	C16—H16B	0.9600
C5—C6	1.375 (2)	C16—H16C	0.9600
C6—H6	0.9300	C17—H17A	0.9600
C6—C7	1.400 (2)	C17—H17B	0.9600
C7—C8	1.433 (2)	C17—H17C	0.9600
C8—C9	1.503 (2)	C18—C19	1.497 (2)
C9—H9A	0.9700	C19—C19^i	1.308 (3)
C9—H9B	0.9700	C19—H19	0.9300
C9—C10	1.514 (2)
C5—O1—C17	116.90 (16)	N2—C11—H11B	109.0
C1—N1—H1	119.0 (17)	N2—C11—C12	113.04 (14)
C2—N1—C1	108.73 (15)	H11A—C11—H11B	107.8
C2—N1—H1	132.3 (17)	C12—C11—H11A	109.0
C10—N2—H2	105.8 (13)	C12—C11—H11B	109.0
C11—N2—C10	112.05 (12)	C11—C12—H12A	109.0
C11—N2—C14	111.85 (13)	C11—C12—H12B	109.0
C11—N2—H2	106.2 (13)	H12A—C12—H12B	107.8
C14—N2—C10	114.43 (12)	C13—C12—C11	112.83 (18)
C14—N2—H2	105.8 (13)	C13—C12—H12A	109.0
N1—C1—H1A	124.8	C13—C12—H12B	109.0
N1—C1—C8	110.45 (17)	C12—C13—H13A	109.5
C8—C1—H1A	124.8	C12—C13—H13B	109.5
N1—C2—C3	131.24 (16)	C12—C13—H13C	109.5
N1—C2—C7	107.90 (15)	H13A—C13—H13B	109.5
C3—C2—C7	120.85 (17)	H13A—C13—H13C	109.5
C2—C3—H3	120.6	H13B—C13—H13C	109.5
C4—C3—C2	118.74 (16)	N2—C14—H14A	108.9
C4—C3—H3	120.6	N2—C14—H14B	108.9
C3—C4—H4	119.5	N2—C14—C15	113.16 (14)
C3—C4—C5	121.06 (17)	H14A—C14—H14B	107.8
C5—C4—H4	119.5	C15—C14—H14A	108.9
O1—C5—C4	115.19 (17)	C15—C14—H14B	108.9
O1—C5—C6	123.99 (17)	C14—C15—H15A	109.2
C6—C5—C4	120.82 (18)	C14—C15—H15B	109.2
C5—C6—H6	120.6	C14—C15—C16	111.96 (18)
C5—C6—C7	118.85 (16)	H15A—C15—H15B	107.9
C7—C6—H6	120.6	C16—C15—H15A	109.2
C2—C7—C8	106.94 (15)	C16—C15—H15B	109.2
C6—C7—C2	119.63 (15)	C15—C16—H16A	109.5
C6—C7—C8	133.41 (15)	C15—C16—H16B	109.5
C1—C8—C7	105.96 (15)	C15—C16—H16C	109.5
C1—C8—C9	128.30 (17)	H16A—C16—H16B	109.5
C7—C8—C9	125.70 (15)	H16A—C16—H16C	109.5
C8—C9—H9A	108.9	H16B—C16—H16C	109.5
C8—C9—H9B	108.9	O1—C17—H17A	109.5
C8—C9—C10	113.31 (14)	O1—C17—H17B	109.5
H9A—C9—H9B	107.7	O1—C17—H17C	109.5
C10—C9—H9A	108.9	H17A—C17—H17B	109.5
C10—C9—H9B	108.9	H17A—C17—H17C	109.5
N2—C10—C9	113.69 (13)	H17B—C17—H17C	109.5
N2—C10—H10A	108.8	O3—C18—C19	115.90 (14)
N2—C10—H10B	108.8	O4—C18—O3	124.28 (15)
C9—C10—H10A	108.8	O4—C18—C19	119.80 (14)
C9—C10—H10B	108.8	C18—C19—H19	117.9
H10A—C10—H10B	107.7	C19^i—C19—C18	124.2 (2)
N2—C11—H11A	109.0	C19^i—C19—H19	117.9
O1—C5—C6—C7	178.60 (17)	C3—C4—C5—O1	−178.61 (17)
O3—C18—C19—C19^i	−174.3 (2)	C3—C4—C5—C6	1.8 (3)
O4—C18—C19—C19^i	4.2 (3)	C4—C5—C6—C7	−1.9 (3)
N1—C1—C8—C7	1.0 (2)	C5—C6—C7—C2	0.2 (2)
N1—C1—C8—C9	−176.59 (16)	C5—C6—C7—C8	178.52 (17)
N1—C2—C3—C4	179.92 (18)	C6—C7—C8—C1	179.95 (18)
N1—C2—C7—C6	−179.66 (15)	C6—C7—C8—C9	−2.4 (3)
N1—C2—C7—C8	1.61 (18)	C7—C2—C3—C4	−1.6 (3)
N2—C11—C12—C13	174.7 (2)	C7—C8—C9—C10	78.1 (2)
N2—C14—C15—C16	178.56 (17)	C8—C9—C10—N2	−164.36 (13)
C1—N1—C2—C3	177.59 (18)	C10—N2—C11—C12	−162.09 (16)
C1—N1—C2—C7	−1.0 (2)	C10—N2—C14—C15	60.72 (19)
C1—C8—C9—C10	−104.8 (2)	C11—N2—C10—C9	−60.66 (18)
C2—N1—C1—C8	0.0 (2)	C11—N2—C14—C15	−170.49 (14)
C2—C3—C4—C5	0.0 (3)	C14—N2—C10—C9	68.03 (18)
C2—C7—C8—C1	−1.58 (19)	C14—N2—C11—C12	67.9 (2)
C2—C7—C8—C9	176.07 (15)	C17—O1—C5—C4	166.9 (2)
C3—C2—C7—C6	1.5 (2)	C17—O1—C5—C6	−13.5 (3)
C3—C2—C7—C8	−177.18 (15)

Symmetry code: (i) −x+1, −y+2, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.98 (2)	1.68 (2)	2.6588 (17)	175 (2)
N1—H1···O4^ii	0.86 (2)	1.91 (3)	2.757 (2)	171 (2)

Symmetry code: (ii) −x+1, −y+2, −z+1.