rac-N-Benzyl-isatincreatinine (unknown solvate).

The title compound, C(19)H(18)N(4)O(3) [systematic name: (RS)-1-benzyl-3-hy-droxy-3-(2-imino-3-methyl-5-oxoimidazolidin-4-yl)-2,3-dihydro-1H-indol-2-one], was prepared as a racemate (RR and SS) by the aldol condensation of N-benzyl-isatin with creatinine in the presence of sodium acetate in acetic acid. The r.m.s. deviation of the isatin ring system is 0.033 Å. The benzyl group is disordered over two orientations, with refined occupancies of 0.847 (7) and 0.153 (7). The dihedral angles between the isatin ring system and the benzene ring (major disorder component) and the imidazole ring are 82.82 (7) and 51.31 (3)°, respectively, In the crystal, mol-ecules are linked into (001) sheets by N-H⋯O and O-H⋯N hydrogen bonds, which incorporate R(2) (2)(9) ring motifs. The crystal was grown from mixed solvents (ethanol, methanol and possibly also ethyl acetate). These solvents are disordered in the crystal and the resulting electron density was found to be uninter-pretable. The solvent contribution to the scattering was removed with the SQUEEZE routine in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148-155]. The formula mass and density do not take account of the solvent.

Related literature

For details on the development of isatin derivatives as anti­cancer agents, see: Penthala et al. (2010a ▶,b ▶). For similar structures, see: Tang et al. (2009 ▶); Penthala et al. (2009a ▶,b ▶).

Experimental

Crystal data

C19H18N4O3

M = 350.37

Orthorhombic,

a = 13.4466 (2) Å

b = 10.6921 (2) Å

c = 27.2057 (5) Å

V = 3911.43 (12) Å3

Z = 8

Cu Kα radiation

μ = 0.68 mm−1

T = 90 K

0.12 × 0.10 × 0.04 mm

Data collection

Bruker X8 Proteum CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.911, T max = 0.973

55165 measured reflections

3602 independent reflections

3344 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.104

S = 1.04

3602 reflections

287 parameters

222 restraints

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELX97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813000378/hb7013sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000378/hb7013Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000378/hb7013Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H18N4O3	F(000) = 1472
Mr = 350.37	Dx = 1.190 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9086 reflections
a = 13.4466 (2) Å	θ = 4.6–68.9°
b = 10.6921 (2) Å	µ = 0.68 mm−1
c = 27.2057 (5) Å	T = 90 K
V = 3911.43 (12) Å3	Plate, pale yellow
Z = 8	0.12 × 0.10 × 0.04 mm

Bruker X8 Proteum CCD diffractometer	3602 independent reflections
Radiation source: fine-focus rotating anode	3344 reflections with I > 2σ(I)
Graded multilayer optics monochromator	Rint = 0.043
Detector resolution: 5.6 pixels mm-1	θmax = 68.7°, θmin = 4.6°
φ and ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2006)	k = −12→12
Tmin = 0.911, Tmax = 0.973	l = −32→31
55165 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0555P)2 + 1.5834P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3602 reflections	Δρmax = 0.28 e Å−3
287 parameters	Δρmin = −0.30 e Å−3
222 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00043 (9)

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.34991 (6)	0.33786 (8)	0.64888 (3)	0.0243 (2)
C1	0.41054 (9)	0.42315 (12)	0.65145 (4)	0.0212 (3)
N2	0.40105 (8)	0.53751 (10)	0.63017 (4)	0.0240 (2)
C3	0.48704 (9)	0.61071 (13)	0.63800 (4)	0.0252 (3)
C4	0.50442 (11)	0.73157 (14)	0.62246 (5)	0.0339 (3)
H4	0.4551	0.7781	0.6054	0.041*
C5	0.59772 (12)	0.78247 (14)	0.63292 (6)	0.0396 (4)
H5	0.6120	0.8657	0.6229	0.047*
C6	0.66974 (11)	0.71461 (14)	0.65753 (5)	0.0359 (3)
H6	0.7331	0.7508	0.6635	0.043*
C7	0.64986 (10)	0.59308 (13)	0.67374 (5)	0.0283 (3)
H7	0.6990	0.5464	0.6909	0.034*
C8	0.55730 (9)	0.54224 (12)	0.66432 (4)	0.0231 (3)
O9	0.56962 (6)	0.31592 (8)	0.66485 (3)	0.0238 (2)
H9	0.5498	0.2516	0.6796	0.036*
C9	0.51144 (9)	0.41884 (11)	0.67907 (4)	0.0202 (3)
C10	0.49128 (8)	0.41474 (11)	0.73572 (4)	0.0180 (3)
H10	0.4592	0.3339	0.7453	0.022*
O11	0.34262 (6)	0.54407 (8)	0.74190 (3)	0.0234 (2)
C11	0.42968 (9)	0.52621 (11)	0.75378 (4)	0.0188 (3)
N12	0.48658 (7)	0.60115 (9)	0.78275 (4)	0.0200 (2)
N13	0.65376 (7)	0.59593 (10)	0.80798 (4)	0.0228 (2)
H13A	0.7113	0.5567	0.8086	0.027*
H13B	0.6474	0.6691	0.8224	0.027*
C13	0.57697 (9)	0.54496 (11)	0.78532 (4)	0.0188 (3)
N14	0.58264 (7)	0.43382 (9)	0.76280 (3)	0.0185 (2)
C14	0.66413 (9)	0.34513 (12)	0.76781 (5)	0.0240 (3)
H14A	0.7141	0.3616	0.7424	0.036*
H14B	0.6386	0.2598	0.7640	0.036*
H14C	0.6945	0.3543	0.8004	0.036*
C15	0.31240 (10)	0.58041 (13)	0.60432 (5)	0.0262 (3)
H15A	0.2929	0.6630	0.6176	0.031*
H15B	0.2574	0.5214	0.6111	0.031*
C16	0.3251 (2)	0.5920 (3)	0.54852 (14)	0.0295 (5)	0.847 (7)
C17	0.2898 (2)	0.6974 (3)	0.52528 (8)	0.0565 (8)	0.847 (7)
H17	0.2631	0.7645	0.5440	0.068*	0.847 (7)
C18	0.2932 (3)	0.7056 (3)	0.47406 (8)	0.0724 (11)	0.847 (7)
H18	0.2687	0.7783	0.4580	0.087*	0.847 (7)
C19	0.3315 (2)	0.6099 (3)	0.44696 (10)	0.0573 (8)	0.847 (7)
H19	0.3337	0.6159	0.4121	0.069*	0.847 (7)
C20	0.3668 (3)	0.5051 (4)	0.46988 (15)	0.0397 (7)	0.847 (7)
H20	0.3936	0.4384	0.4509	0.048*	0.847 (7)
C21	0.3636 (3)	0.4957 (4)	0.52102 (15)	0.0313 (7)	0.847 (7)
H21	0.3881	0.4227	0.5368	0.038*	0.847 (7)
C16'	0.3153 (14)	0.5782 (19)	0.5524 (9)	0.0295 (5)	0.153 (7)
C17'	0.2496 (12)	0.6474 (16)	0.5261 (4)	0.054 (2)	0.153 (7)
H17'	0.2047	0.7002	0.5433	0.065*	0.153 (7)
C18'	0.2450 (13)	0.6442 (17)	0.4741 (4)	0.060 (2)	0.153 (7)
H18'	0.1982	0.6935	0.4565	0.072*	0.153 (7)
C19'	0.3107 (13)	0.5673 (16)	0.4500 (6)	0.054 (2)	0.153 (7)
H19'	0.3098	0.5632	0.4151	0.065*	0.153 (7)
C20'	0.3770 (18)	0.497 (2)	0.4756 (9)	0.042 (2)	0.153 (7)
H20'	0.4220	0.4438	0.4587	0.050*	0.153 (7)
C21'	0.3787 (17)	0.503 (2)	0.5264 (9)	0.033 (2)	0.153 (7)
H21'	0.4255	0.4533	0.5439	0.040*	0.153 (7)

	U11	U22	U33	U12	U13	U23
O1	0.0232 (4)	0.0268 (5)	0.0229 (4)	−0.0029 (4)	−0.0027 (3)	0.0017 (4)
C1	0.0227 (6)	0.0254 (6)	0.0154 (5)	−0.0006 (5)	0.0014 (4)	0.0013 (5)
N2	0.0241 (5)	0.0277 (6)	0.0202 (5)	−0.0014 (4)	−0.0022 (4)	0.0059 (4)
C3	0.0273 (6)	0.0290 (7)	0.0193 (6)	−0.0040 (5)	0.0020 (5)	0.0038 (5)
C4	0.0402 (8)	0.0320 (7)	0.0295 (7)	−0.0029 (6)	−0.0008 (6)	0.0104 (6)
C5	0.0493 (9)	0.0330 (8)	0.0364 (8)	−0.0140 (7)	0.0008 (7)	0.0116 (6)
C6	0.0373 (8)	0.0409 (8)	0.0295 (7)	−0.0162 (6)	0.0000 (6)	0.0063 (6)
C7	0.0280 (7)	0.0359 (7)	0.0210 (6)	−0.0067 (6)	0.0015 (5)	0.0040 (5)
C8	0.0257 (6)	0.0276 (6)	0.0161 (6)	−0.0036 (5)	0.0023 (5)	0.0027 (5)
O9	0.0236 (4)	0.0257 (5)	0.0221 (4)	0.0010 (3)	0.0040 (3)	−0.0004 (3)
C9	0.0199 (6)	0.0230 (6)	0.0178 (6)	−0.0008 (5)	0.0006 (4)	0.0010 (4)
C10	0.0172 (6)	0.0189 (6)	0.0178 (6)	−0.0008 (4)	−0.0004 (4)	0.0016 (4)
O11	0.0178 (4)	0.0229 (4)	0.0295 (5)	0.0006 (3)	−0.0024 (3)	0.0009 (3)
C11	0.0181 (6)	0.0203 (6)	0.0179 (5)	−0.0011 (4)	0.0011 (4)	0.0040 (4)
N12	0.0182 (5)	0.0209 (5)	0.0208 (5)	0.0006 (4)	−0.0003 (4)	−0.0001 (4)
N13	0.0191 (5)	0.0234 (5)	0.0258 (5)	0.0024 (4)	−0.0041 (4)	−0.0046 (4)
C13	0.0196 (6)	0.0223 (6)	0.0146 (5)	−0.0002 (5)	0.0007 (4)	0.0031 (4)
N14	0.0181 (5)	0.0187 (5)	0.0186 (5)	0.0014 (4)	−0.0015 (4)	0.0001 (4)
C14	0.0198 (6)	0.0215 (6)	0.0308 (6)	0.0028 (5)	−0.0044 (5)	−0.0001 (5)
C15	0.0248 (6)	0.0340 (7)	0.0199 (6)	0.0057 (5)	0.0006 (5)	0.0044 (5)
C16	0.0267 (10)	0.0427 (11)	0.0191 (9)	0.0057 (7)	0.0021 (7)	0.0076 (7)
C17	0.0808 (19)	0.0593 (16)	0.0294 (9)	0.0366 (14)	0.0088 (11)	0.0144 (10)
C18	0.106 (2)	0.078 (2)	0.0330 (10)	0.0440 (19)	0.0066 (13)	0.0227 (12)
C19	0.0693 (17)	0.083 (2)	0.0196 (9)	0.0199 (15)	0.0079 (10)	0.0136 (12)
C20	0.0358 (13)	0.0602 (14)	0.0230 (14)	0.0012 (11)	0.0021 (10)	−0.0050 (11)
C21	0.0316 (15)	0.0380 (11)	0.0243 (14)	−0.0012 (10)	−0.0027 (9)	−0.0008 (9)
C16'	0.0267 (10)	0.0427 (11)	0.0191 (9)	0.0057 (7)	0.0021 (7)	0.0076 (7)
C17'	0.068 (4)	0.064 (4)	0.030 (3)	0.024 (4)	0.005 (4)	0.012 (4)
C18'	0.081 (5)	0.072 (5)	0.026 (3)	0.031 (4)	−0.002 (4)	0.019 (4)
C19'	0.069 (4)	0.075 (5)	0.019 (4)	0.014 (4)	−0.001 (4)	0.008 (4)
C20'	0.044 (4)	0.059 (4)	0.023 (4)	0.005 (4)	0.000 (4)	0.001 (4)
C21'	0.029 (4)	0.051 (4)	0.020 (4)	−0.003 (4)	−0.001 (4)	0.004 (4)

O1—C1	1.2253 (15)	C14—H14A	0.9800
C1—N2	1.3588 (16)	C14—H14B	0.9800
C1—C9	1.5516 (16)	C14—H14C	0.9800
N2—C3	1.4124 (17)	C15—C16'	1.41 (2)
N2—C15	1.4582 (16)	C15—C16	1.533 (4)
C3—C4	1.3796 (19)	C15—H15A	0.9900
C3—C8	1.3933 (18)	C15—H15B	0.9900
C4—C5	1.397 (2)	C16—C21	1.374 (3)
C4—H4	0.9500	C16—C17	1.377 (3)
C5—C6	1.383 (2)	C17—C18	1.397 (3)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.398 (2)	C18—C19	1.362 (4)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.3821 (18)	C19—C20	1.368 (4)
C7—H7	0.9500	C19—H19	0.9500
C8—C9	1.5107 (17)	C20—C21	1.396 (3)
O9—C9	1.4046 (15)	C20—H20	0.9500
O9—H9	0.8400	C21—H21	0.9500
C9—C10	1.5654 (16)	C16'—C17'	1.357 (16)
C10—N14	1.4468 (14)	C16'—C21'	1.368 (17)
C10—C11	1.5322 (16)	C17'—C18'	1.418 (13)
C10—H10	1.0000	C17'—H17'	0.9500
O11—C11	1.2295 (14)	C18'—C19'	1.373 (15)
C11—N12	1.3597 (16)	C18'—H18'	0.9500
N12—C13	1.3576 (15)	C19'—C20'	1.359 (16)
N13—C13	1.3204 (15)	C19'—H19'	0.9500
N13—H13A	0.8800	C20'—C21'	1.385 (17)
N13—H13B	0.8800	C20'—H20'	0.9500
C13—N14	1.3392 (16)	C21'—H21'	0.9500
N14—C14	1.4555 (15)
O1—C1—N2	125.66 (11)	N14—C14—H14B	109.5
O1—C1—C9	125.97 (11)	H14A—C14—H14B	109.5
N2—C1—C9	108.37 (10)	N14—C14—H14C	109.5
C1—N2—C3	110.95 (10)	H14A—C14—H14C	109.5
C1—N2—C15	124.43 (11)	H14B—C14—H14C	109.5
C3—N2—C15	124.59 (11)	C16'—C15—N2	117.0 (8)
C4—C3—C8	122.34 (12)	N2—C15—C16	114.35 (15)
C4—C3—N2	127.69 (12)	C16'—C15—H15A	112.9
C8—C3—N2	109.96 (11)	N2—C15—H15A	108.7
C3—C4—C5	117.03 (13)	C16—C15—H15A	108.7
C3—C4—H4	121.5	C16'—C15—H15B	101.4
C5—C4—H4	121.5	N2—C15—H15B	108.7
C6—C5—C4	121.55 (13)	C16—C15—H15B	108.7
C6—C5—H5	119.2	H15A—C15—H15B	107.6
C4—C5—H5	119.2	C21—C16—C17	119.6 (3)
C5—C6—C7	120.43 (13)	C21—C16—C15	121.4 (3)
C5—C6—H6	119.8	C17—C16—C15	118.9 (3)
C7—C6—H6	119.8	C16—C17—C18	119.8 (3)
C8—C7—C6	118.64 (13)	C16—C17—H17	120.1
C8—C7—H7	120.7	C18—C17—H17	120.1
C6—C7—H7	120.7	C19—C18—C17	120.4 (2)
C7—C8—C3	119.95 (12)	C19—C18—H18	119.8
C7—C8—C9	131.44 (12)	C17—C18—H18	119.8
C3—C8—C9	108.58 (11)	C18—C19—C20	120.0 (3)
C9—O9—H9	109.5	C18—C19—H19	120.0
O9—C9—C8	112.56 (10)	C20—C19—H19	120.0
O9—C9—C1	112.14 (10)	C19—C20—C21	120.2 (3)
C8—C9—C1	101.67 (9)	C19—C20—H20	119.9
O9—C9—C10	110.23 (9)	C21—C20—H20	119.9
C8—C9—C10	110.90 (9)	C16—C21—C20	120.0 (3)
C1—C9—C10	109.04 (9)	C16—C21—H21	120.0
N14—C10—C11	100.73 (9)	C20—C21—H21	120.0
N14—C10—C9	110.50 (9)	C17'—C16'—C21'	117.0 (18)
C11—C10—C9	112.80 (9)	C17'—C16'—C15	120.0 (18)
N14—C10—H10	110.8	C21'—C16'—C15	123.0 (16)
C11—C10—H10	110.8	C16'—C17'—C18'	122.8 (14)
C9—C10—H10	110.8	C16'—C17'—H17'	118.6
O11—C11—N12	126.63 (11)	C18'—C17'—H17'	118.6
O11—C11—C10	123.45 (11)	C19'—C18'—C17'	117.6 (12)
N12—C11—C10	109.88 (10)	C19'—C18'—H18'	121.2
C13—N12—C11	105.83 (10)	C17'—C18'—H18'	121.2
C13—N13—H13A	120.0	C20'—C19'—C18'	120.5 (16)
C13—N13—H13B	120.0	C20'—C19'—H19'	119.8
H13A—N13—H13B	120.0	C18'—C19'—H19'	119.8
N13—C13—N14	122.37 (11)	C19'—C20'—C21'	119.9 (19)
N13—C13—N12	122.79 (11)	C19'—C20'—H20'	120.0
N14—C13—N12	114.84 (10)	C21'—C20'—H20'	120.0
C13—N14—C10	108.04 (9)	C16'—C21'—C20'	122.2 (19)
C13—N14—C14	125.31 (10)	C16'—C21'—H21'	118.9
C10—N14—C14	126.52 (10)	C20'—C21'—H21'	118.9
N14—C14—H14A	109.5
O1—C1—N2—C3	−176.47 (11)	O11—C11—N12—C13	−179.47 (11)
C9—C1—N2—C3	3.04 (13)	C10—C11—N12—C13	−1.45 (12)
O1—C1—N2—C15	5.67 (19)	C11—N12—C13—N13	175.47 (11)
C9—C1—N2—C15	−174.83 (10)	C11—N12—C13—N14	−4.15 (13)
C1—N2—C3—C4	−179.33 (13)	N13—C13—N14—C10	−171.44 (10)
C15—N2—C3—C4	−1.5 (2)	N12—C13—N14—C10	8.18 (13)
C1—N2—C3—C8	1.47 (14)	N13—C13—N14—C14	12.39 (18)
C15—N2—C3—C8	179.33 (11)	N12—C13—N14—C14	−167.99 (10)
C8—C3—C4—C5	1.9 (2)	C11—C10—N14—C13	−7.92 (11)
N2—C3—C4—C5	−177.19 (13)	C9—C10—N14—C13	111.54 (10)
C3—C4—C5—C6	0.3 (2)	C11—C10—N14—C14	168.19 (10)
C4—C5—C6—C7	−1.5 (2)	C9—C10—N14—C14	−72.35 (14)
C5—C6—C7—C8	0.5 (2)	C1—N2—C15—C16'	−101.9 (9)
C6—C7—C8—C3	1.71 (19)	C3—N2—C15—C16'	80.6 (9)
C6—C7—C8—C9	−176.14 (13)	C1—N2—C15—C16	−109.52 (19)
C4—C3—C8—C7	−3.0 (2)	C3—N2—C15—C16	72.9 (2)
N2—C3—C8—C7	176.26 (11)	C16'—C15—C16—C21	−62 (8)
C4—C3—C8—C9	175.30 (12)	N2—C15—C16—C21	50.4 (3)
N2—C3—C8—C9	−5.45 (14)	C16'—C15—C16—C17	113 (8)
C7—C8—C9—O9	−55.07 (17)	N2—C15—C16—C17	−134.8 (2)
C3—C8—C9—O9	126.90 (11)	C21—C16—C17—C18	0.11 (19)
C7—C8—C9—C1	−175.25 (13)	C15—C16—C17—C18	−174.8 (2)
C3—C8—C9—C1	6.72 (12)	C16—C17—C18—C19	−0.1 (2)
C7—C8—C9—C10	68.94 (17)	C17—C18—C19—C20	0.0 (4)
C3—C8—C9—C10	−109.09 (11)	C18—C19—C20—C21	0.1 (4)
O1—C1—C9—O9	53.15 (15)	C17—C16—C21—C20	0.0 (3)
N2—C1—C9—O9	−126.36 (11)	C15—C16—C21—C20	174.8 (2)
O1—C1—C9—C8	173.61 (11)	C19—C20—C21—C16	−0.1 (4)
N2—C1—C9—C8	−5.89 (12)	N2—C15—C16'—C17'	−161.4 (9)
O1—C1—C9—C10	−69.22 (15)	C16—C15—C16'—C17'	−91 (8)
N2—C1—C9—C10	111.28 (11)	N2—C15—C16'—C21'	22.3 (12)
O9—C9—C10—N14	67.00 (12)	C16—C15—C16'—C21'	93 (8)
C8—C9—C10—N14	−58.33 (12)	C21'—C16'—C17'—C18'	−0.1 (3)
C1—C9—C10—N14	−169.48 (10)	C15—C16'—C17'—C18'	−176.5 (14)
O9—C9—C10—C11	178.88 (9)	C16'—C17'—C18'—C19'	−0.1 (3)
C8—C9—C10—C11	53.55 (13)	C17'—C18'—C19'—C20'	0.2 (7)
C1—C9—C10—C11	−57.60 (12)	C18'—C19'—C20'—C21'	−0.2 (9)
N14—C10—C11—O11	−176.13 (11)	C17'—C16'—C21'—C20'	0.1 (7)
C9—C10—C11—O11	66.08 (14)	C15—C16'—C21'—C20'	176.5 (14)
N14—C10—C11—N12	5.78 (12)	C19'—C20'—C21'—C16'	0.0 (10)
C9—C10—C11—N12	−112.01 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9···N12i	0.84	1.97	2.8065 (13)	175
N13—H13A···O11ii	0.88	2.24	2.9321 (13)	135
N13—H13B···O1iii	0.88	1.97	2.8410 (14)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9⋯N12i	0.84	1.97	2.8065 (13)	175
N13—H13A⋯O11ii	0.88	2.24	2.9321 (13)	135
N13—H13B⋯O1iii	0.88	1.97	2.8410 (14)	173

Symmetry codes: (i) ; (ii) ; (iii) .