3',6'-Bis(ethyl-amino)-2-[(2-hydroxy-ethyl)-amino]-2',7'-dimethylspiro-[isoindoline-1,9'-xanthen]-3-one.

In the title compound, C(28)H(32)N(4)O(3), the dihedral angle between the planes of the xanthene ring system and the spiro-lactam ring is 85.99 (3)°. Mol-ecules are linked by inter-molecular O-H⋯O and N-H⋯O hydrogen-bonding inter-actions.

Related literature

For the synthesis and related structures of rhodamine dyes, see: Ko et al. (2006 ▶); Wu et al. (2007 ▶); Zhang et al. (2008 ▶). For related literature on the photophysical properties and applications of rhodamine dyes, see: Lakowicz (2006 ▶).

Experimental

Crystal data

C28H32N4O3

M = 472.58

Triclinic,

a = 9.3195 (18) Å

b = 9.4770 (16) Å

c = 15.384 (3) Å

α = 94.722 (18)°

β = 107.592 (13)°

γ = 98.924 (13)°

V = 1267.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 298 (2) K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: none

8770 measured reflections

4305 independent reflections

3144 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.121

S = 1.06

4305 reflections

325 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023611/zl2122sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023611/zl2122Isup2.hkl

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

C28H32N4O3	Z = 2
Mr = 472.58	F000 = 504
Triclinic, P1	Dx = 1.238 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.3195 (18) Å	Cell parameters from 2583 reflections
b = 9.4770 (16) Å	θ = 2.3–26.8º
c = 15.384 (3) Å	µ = 0.08 mm−1
α = 94.722 (18)º	T = 298 (2) K
β = 107.592 (13)º	Block, colourless
γ = 98.924 (13)º	0.30 × 0.20 × 0.15 mm
V = 1267.4 (4) Å3

Bruker APEXII CCD area-detector diffractometer	3144 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Monochromator: graphite	θmax = 25.0º
T = 298(2) K	θmin = 2.2º
φ and ω scans	h = −11→11
Absorption correction: none	k = −11→11
8770 measured reflections	l = −18→18
4305 independent 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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.068P)2 + 0.1313P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
4305 reflections	Δρmax = 0.34 e Å−3
325 parameters	Δρmin = −0.19 e Å−3
4 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (8)

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.

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
O2	0.69421 (15)	0.29618 (12)	0.25724 (9)	0.0457 (3)
C16	0.8939 (2)	0.3280 (2)	0.19461 (12)	0.0433 (5)
H16A	0.8966	0.2307	0.1971	0.052*
C14	0.5894 (2)	0.35022 (18)	0.29116 (11)	0.0364 (4)
C10	0.4573 (2)	0.52933 (18)	0.32506 (12)	0.0393 (4)
H10A	0.4422	0.6240	0.3249	0.047*
C9	0.5676 (2)	0.49027 (17)	0.28839 (11)	0.0346 (4)
C20	0.7802 (2)	0.53260 (18)	0.22210 (11)	0.0353 (4)
N1	0.73649 (16)	0.72826 (14)	0.32209 (9)	0.0371 (4)
C8	0.66223 (19)	0.59937 (17)	0.25166 (11)	0.0342 (4)
C15	0.7889 (2)	0.38924 (18)	0.22530 (11)	0.0374 (4)
C13	0.5043 (2)	0.25175 (19)	0.32712 (13)	0.0441 (5)
H13A	0.5219	0.1578	0.3280	0.053*
C17	0.9953 (2)	0.4115 (2)	0.16000 (12)	0.0443 (5)
C19	0.8840 (2)	0.6140 (2)	0.18778 (12)	0.0425 (4)
H19A	0.8801	0.7111	0.1853	0.051*
C11	0.3697 (2)	0.43659 (19)	0.36141 (12)	0.0410 (4)
O1	0.72540 (17)	0.96667 (13)	0.35009 (10)	0.0621 (4)
N4	1.0976 (2)	0.3528 (2)	0.12588 (12)	0.0589 (5)
H4A	1.175 (2)	0.413 (2)	0.1209 (16)	0.071*
C7	0.56703 (19)	0.67124 (18)	0.17571 (11)	0.0354 (4)
C12	0.3930 (2)	0.29227 (19)	0.36189 (12)	0.0431 (5)
C18	0.9910 (2)	0.5596 (2)	0.15757 (12)	0.0449 (5)
N2	0.82046 (17)	0.70879 (16)	0.41102 (10)	0.0422 (4)
H2A	0.787 (2)	0.7625 (19)	0.4486 (12)	0.051*
C2	0.5870 (2)	0.81693 (19)	0.20269 (12)	0.0414 (4)
N3	0.3075 (2)	0.19768 (18)	0.39963 (14)	0.0619 (5)
H3A	0.216 (2)	0.216 (2)	0.3996 (16)	0.074*
C21	0.2564 (3)	0.4877 (2)	0.40272 (15)	0.0576 (5)
H21A	0.2557	0.5875	0.3962	0.086*
H21B	0.2854	0.4766	0.4668	0.086*
H21C	0.1559	0.4317	0.3714	0.086*
C1	0.6898 (2)	0.85141 (18)	0.29889 (13)	0.0422 (4)
C6	0.4744 (2)	0.6098 (2)	0.08895 (12)	0.0443 (5)
H6A	0.4597	0.5111	0.0707	0.053*
C26	1.1000 (3)	0.6534 (2)	0.12199 (15)	0.0609 (6)
H26A	1.0818	0.7503	0.1259	0.091*
H26B	1.0843	0.6173	0.0590	0.091*
H26C	1.2035	0.6524	0.1584	0.091*
C5	0.4036 (2)	0.6986 (3)	0.02931 (13)	0.0561 (6)
H5A	0.3403	0.6588	−0.0297	0.067*
C4	0.4252 (3)	0.8445 (3)	0.05583 (15)	0.0609 (6)
H4B	0.3777	0.9021	0.0142	0.073*
C3	0.5162 (3)	0.9066 (2)	0.14321 (15)	0.0565 (6)
H3B	0.5299	1.0050	0.1617	0.068*
C22	0.3242 (3)	0.0484 (2)	0.40404 (18)	0.0770 (7)
H22A	0.2842	0.0130	0.4511	0.092*
H22B	0.4325	0.0445	0.4227	0.092*
C25	1.2242 (4)	0.1710 (4)	0.0779 (2)	0.1053 (11)
H25A	1.2292	0.0705	0.0766	0.158*
H25B	1.3230	0.2277	0.1123	0.158*
H25C	1.1947	0.1941	0.0161	0.158*
C24	1.1072 (3)	0.2038 (3)	0.12294 (18)	0.0750 (7)
H24A	1.0077	0.1456	0.0886	0.090*
H24B	1.1361	0.1791	0.1850	0.090*
C23	0.2464 (4)	−0.0473 (3)	0.3172 (2)	0.1070 (11)
H23A	0.2638	−0.1433	0.3251	0.160*
H23B	0.2859	−0.0138	0.2703	0.160*
H23C	0.1383	−0.0475	0.2995	0.160*
C28	1.0649 (2)	0.7337 (2)	0.52897 (13)	0.0526 (5)
H28A	1.0422	0.6325	0.5356	0.063*
H28B	1.1749	0.7618	0.5430	0.063*
C27	0.9862 (2)	0.7548 (2)	0.43216 (13)	0.0529 (5)
H27A	1.0096	0.8557	0.4249	0.063*
H27B	1.0219	0.6986	0.3901	0.063*
O3	1.01619 (16)	0.81677 (16)	0.59124 (9)	0.0627 (4)
H3C	1.0814	0.8896	0.6149	0.094*

	U11	U22	U33	U12	U13	U23
O2	0.0503 (8)	0.0360 (7)	0.0620 (8)	0.0138 (6)	0.0308 (7)	0.0100 (6)
C16	0.0461 (11)	0.0459 (10)	0.0416 (10)	0.0196 (9)	0.0147 (9)	0.0048 (8)
C14	0.0355 (10)	0.0375 (9)	0.0364 (9)	0.0076 (8)	0.0123 (8)	0.0030 (7)
C10	0.0409 (11)	0.0355 (9)	0.0440 (10)	0.0087 (8)	0.0167 (9)	0.0051 (8)
C9	0.0357 (10)	0.0342 (9)	0.0333 (9)	0.0050 (7)	0.0111 (8)	0.0036 (7)
C20	0.0347 (10)	0.0390 (9)	0.0325 (9)	0.0078 (8)	0.0112 (8)	0.0025 (7)
N1	0.0386 (9)	0.0354 (8)	0.0364 (8)	0.0039 (6)	0.0131 (7)	0.0015 (6)
C8	0.0358 (10)	0.0333 (9)	0.0336 (9)	0.0051 (7)	0.0130 (8)	0.0004 (7)
C15	0.0368 (10)	0.0412 (10)	0.0336 (9)	0.0080 (8)	0.0103 (8)	0.0037 (7)
C13	0.0489 (12)	0.0335 (9)	0.0525 (11)	0.0073 (8)	0.0196 (9)	0.0089 (8)
C17	0.0381 (11)	0.0623 (12)	0.0342 (10)	0.0176 (9)	0.0109 (8)	0.0021 (8)
C19	0.0421 (11)	0.0439 (10)	0.0447 (10)	0.0081 (8)	0.0184 (9)	0.0069 (8)
C11	0.0392 (11)	0.0430 (10)	0.0431 (10)	0.0052 (8)	0.0183 (9)	0.0043 (8)
O1	0.0694 (10)	0.0368 (7)	0.0717 (10)	0.0053 (7)	0.0168 (8)	−0.0085 (7)
N4	0.0516 (12)	0.0751 (13)	0.0613 (11)	0.0260 (10)	0.0282 (9)	0.0067 (9)
C7	0.0344 (10)	0.0409 (9)	0.0361 (9)	0.0091 (7)	0.0170 (8)	0.0082 (7)
C12	0.0442 (11)	0.0432 (10)	0.0431 (10)	0.0024 (8)	0.0181 (9)	0.0078 (8)
C18	0.0409 (11)	0.0559 (11)	0.0405 (10)	0.0086 (9)	0.0177 (9)	0.0042 (8)
N2	0.0365 (9)	0.0524 (9)	0.0341 (8)	0.0025 (7)	0.0100 (7)	0.0016 (7)
C2	0.0420 (11)	0.0412 (10)	0.0465 (11)	0.0110 (8)	0.0193 (9)	0.0103 (8)
N3	0.0665 (13)	0.0475 (10)	0.0872 (13)	0.0061 (9)	0.0472 (11)	0.0188 (9)
C21	0.0587 (14)	0.0569 (12)	0.0715 (14)	0.0131 (10)	0.0391 (12)	0.0143 (10)
C1	0.0452 (11)	0.0318 (9)	0.0529 (11)	0.0036 (8)	0.0229 (9)	0.0030 (8)
C6	0.0424 (11)	0.0547 (11)	0.0391 (10)	0.0133 (9)	0.0165 (9)	0.0034 (8)
C26	0.0521 (13)	0.0742 (14)	0.0654 (14)	0.0082 (11)	0.0337 (11)	0.0098 (11)
C5	0.0484 (13)	0.0871 (16)	0.0380 (11)	0.0237 (11)	0.0157 (9)	0.0102 (10)
C4	0.0665 (15)	0.0788 (16)	0.0540 (13)	0.0355 (12)	0.0269 (12)	0.0315 (11)
C3	0.0665 (14)	0.0491 (11)	0.0667 (14)	0.0234 (10)	0.0304 (12)	0.0209 (10)
C22	0.092 (2)	0.0648 (15)	0.0916 (19)	0.0074 (13)	0.0534 (16)	0.0264 (13)
C25	0.099 (2)	0.125 (2)	0.117 (2)	0.064 (2)	0.0545 (19)	−0.0001 (19)
C24	0.0710 (17)	0.0829 (17)	0.0834 (17)	0.0393 (14)	0.0322 (14)	0.0044 (13)
C23	0.139 (3)	0.0716 (18)	0.117 (3)	−0.0130 (18)	0.070 (2)	0.0006 (17)
C28	0.0421 (12)	0.0554 (12)	0.0539 (12)	0.0079 (9)	0.0088 (10)	−0.0005 (9)
C27	0.0392 (12)	0.0676 (13)	0.0495 (12)	0.0039 (10)	0.0148 (9)	0.0041 (9)
O3	0.0519 (9)	0.0710 (9)	0.0563 (9)	−0.0028 (7)	0.0162 (7)	−0.0104 (7)

O2—C15	1.375 (2)	C2—C1	1.477 (3)
O2—C14	1.381 (2)	N3—C22	1.452 (3)
C16—C15	1.388 (2)	N3—H3A	0.898 (16)
C16—C17	1.394 (3)	C21—H21A	0.9600
C16—H16A	0.9300	C21—H21B	0.9600
C14—C9	1.376 (2)	C21—H21C	0.9600
C14—C13	1.388 (3)	C6—C5	1.385 (3)
C10—C11	1.373 (3)	C6—H6A	0.9300
C10—C9	1.395 (2)	C26—H26A	0.9600
C10—H10A	0.9300	C26—H26B	0.9600
C9—C8	1.510 (2)	C26—H26C	0.9600
C20—C15	1.378 (2)	C5—C4	1.375 (3)
C20—C19	1.397 (2)	C5—H5A	0.9300
C20—C8	1.512 (2)	C4—C3	1.378 (3)
N1—C1	1.346 (2)	C4—H4B	0.9300
N1—N2	1.399 (2)	C3—H3B	0.9300
N1—C8	1.487 (2)	C22—C23	1.464 (4)
C8—C7	1.519 (2)	C22—H22A	0.9700
C13—C12	1.391 (3)	C22—H22B	0.9700
C13—H13A	0.9300	C25—C24	1.514 (3)
C17—N4	1.383 (2)	C25—H25A	0.9600
C17—C18	1.413 (3)	C25—H25B	0.9600
C19—C18	1.370 (2)	C25—H25C	0.9600
C19—H19A	0.9300	C24—H24A	0.9700
C11—C12	1.418 (2)	C24—H24B	0.9700
C11—C21	1.506 (2)	C23—H23A	0.9600
O1—C1	1.229 (2)	C23—H23B	0.9600
N4—C24	1.426 (3)	C23—H23C	0.9600
N4—H4A	0.872 (16)	C28—O3	1.412 (2)
C7—C6	1.373 (2)	C28—C27	1.493 (3)
C7—C2	1.376 (2)	C28—H28A	0.9700
C12—N3	1.386 (2)	C28—H28B	0.9700
C18—C26	1.502 (3)	C27—H27A	0.9700
N2—C27	1.465 (2)	C27—H27B	0.9700
N2—H2A	0.892 (14)	O3—H3C	0.8200
C2—C3	1.390 (3)
C15—O2—C14	118.45 (13)	H21A—C21—H21B	109.5
C15—C16—C17	120.39 (17)	C11—C21—H21C	109.5
C15—C16—H16A	119.8	H21A—C21—H21C	109.5
C17—C16—H16A	119.8	H21B—C21—H21C	109.5
C9—C14—O2	123.10 (16)	O1—C1—N1	125.40 (18)
C9—C14—C13	121.84 (16)	O1—C1—C2	128.51 (17)
O2—C14—C13	115.05 (15)	N1—C1—C2	106.06 (14)
C11—C10—C9	124.05 (16)	C7—C6—C5	118.23 (18)
C11—C10—H10A	118.0	C7—C6—H6A	120.9
C9—C10—H10A	118.0	C5—C6—H6A	120.9
C14—C9—C10	116.65 (16)	C18—C26—H26A	109.5
C14—C9—C8	122.29 (15)	C18—C26—H26B	109.5
C10—C9—C8	121.01 (14)	H26A—C26—H26B	109.5
C15—C20—C19	116.72 (16)	C18—C26—H26C	109.5
C15—C20—C8	122.27 (16)	H26A—C26—H26C	109.5
C19—C20—C8	120.99 (15)	H26B—C26—H26C	109.5
C1—N1—N2	124.66 (14)	C4—C5—C6	121.15 (19)
C1—N1—C8	114.93 (14)	C4—C5—H5A	119.4
N2—N1—C8	118.93 (13)	C6—C5—H5A	119.4
N1—C8—C9	110.24 (13)	C5—C4—C3	120.93 (19)
N1—C8—C20	111.05 (13)	C5—C4—H4B	119.5
C9—C8—C20	110.54 (13)	C3—C4—H4B	119.5
N1—C8—C7	99.20 (12)	C4—C3—C2	117.61 (19)
C9—C8—C7	113.69 (14)	C4—C3—H3B	121.2
C20—C8—C7	111.64 (13)	C2—C3—H3B	121.2
O2—C15—C20	123.17 (15)	N3—C22—C23	114.1 (2)
O2—C15—C16	115.15 (15)	N3—C22—H22A	108.7
C20—C15—C16	121.68 (17)	C23—C22—H22A	108.7
C14—C13—C12	120.58 (16)	N3—C22—H22B	108.7
C14—C13—H13A	119.7	C23—C22—H22B	108.7
C12—C13—H13A	119.7	H22A—C22—H22B	107.6
N4—C17—C16	121.86 (18)	C24—C25—H25A	109.5
N4—C17—C18	118.95 (18)	C24—C25—H25B	109.5
C16—C17—C18	119.18 (16)	H25A—C25—H25B	109.5
C18—C19—C20	124.05 (17)	C24—C25—H25C	109.5
C18—C19—H19A	118.0	H25A—C25—H25C	109.5
C20—C19—H19A	118.0	H25B—C25—H25C	109.5
C10—C11—C12	117.97 (16)	N4—C24—C25	110.7 (2)
C10—C11—C21	121.09 (16)	N4—C24—H24A	109.5
C12—C11—C21	120.90 (16)	C25—C24—H24A	109.5
C17—N4—C24	123.02 (19)	N4—C24—H24B	109.5
C17—N4—H4A	116.6 (15)	C25—C24—H24B	109.5
C24—N4—H4A	118.1 (15)	H24A—C24—H24B	108.1
C6—C7—C2	120.62 (16)	C22—C23—H23A	109.5
C6—C7—C8	128.39 (15)	C22—C23—H23B	109.5
C2—C7—C8	110.96 (15)	H23A—C23—H23B	109.5
N3—C12—C13	122.25 (17)	C22—C23—H23C	109.5
N3—C12—C11	118.83 (17)	H23A—C23—H23C	109.5
C13—C12—C11	118.89 (16)	H23B—C23—H23C	109.5
C19—C18—C17	117.97 (17)	O3—C28—C27	110.65 (16)
C19—C18—C26	121.36 (18)	O3—C28—H28A	109.5
C17—C18—C26	120.67 (17)	C27—C28—H28A	109.5
N1—N2—C27	113.12 (14)	O3—C28—H28B	109.5
N1—N2—H2A	105.2 (12)	C27—C28—H28B	109.5
C27—N2—H2A	109.7 (13)	H28A—C28—H28B	108.1
C7—C2—C3	121.43 (18)	N2—C27—C28	109.01 (16)
C7—C2—C1	108.54 (15)	N2—C27—H27A	109.9
C3—C2—C1	130.03 (17)	C28—C27—H27A	109.9
C12—N3—C22	122.85 (18)	N2—C27—H27B	109.9
C12—N3—H3A	117.2 (16)	C28—C27—H27B	109.9
C22—N3—H3A	115.2 (16)	H27A—C27—H27B	108.3
C11—C21—H21A	109.5	C28—O3—H3C	109.5
C11—C21—H21B	109.5
C15—O2—C14—C9	4.9 (2)	C9—C8—C7—C6	−65.7 (2)
C15—O2—C14—C13	−176.33 (15)	C20—C8—C7—C6	60.2 (2)
O2—C14—C9—C10	179.82 (15)	N1—C8—C7—C2	−0.61 (17)
C13—C14—C9—C10	1.1 (3)	C9—C8—C7—C2	116.38 (16)
O2—C14—C9—C8	−2.9 (3)	C20—C8—C7—C2	−117.72 (16)
C13—C14—C9—C8	178.39 (15)	C14—C13—C12—N3	−178.99 (18)
C11—C10—C9—C14	−1.2 (3)	C14—C13—C12—C11	−1.1 (3)
C11—C10—C9—C8	−178.52 (16)	C10—C11—C12—N3	178.97 (18)
C1—N1—C8—C9	−115.45 (16)	C21—C11—C12—N3	1.2 (3)
N2—N1—C8—C9	51.36 (19)	C10—C11—C12—C13	1.0 (3)
C1—N1—C8—C20	121.68 (16)	C21—C11—C12—C13	−176.80 (17)
N2—N1—C8—C20	−71.50 (18)	C20—C19—C18—C17	1.0 (3)
C1—N1—C8—C7	4.12 (17)	C20—C19—C18—C26	−179.60 (17)
N2—N1—C8—C7	170.93 (14)	N4—C17—C18—C19	177.03 (17)
C14—C9—C8—N1	−124.27 (17)	C16—C17—C18—C19	−1.4 (3)
C10—C9—C8—N1	52.9 (2)	N4—C17—C18—C26	−2.4 (3)
C14—C9—C8—C20	−1.1 (2)	C16—C17—C18—C26	179.15 (17)
C10—C9—C8—C20	176.09 (14)	C1—N1—N2—C27	−86.1 (2)
C14—C9—C8—C7	125.37 (17)	C8—N1—N2—C27	108.48 (17)
C10—C9—C8—C7	−57.4 (2)	C6—C7—C2—C3	−0.8 (3)
C15—C20—C8—N1	125.88 (17)	C8—C7—C2—C3	177.32 (17)
C19—C20—C8—N1	−55.7 (2)	C6—C7—C2—C1	179.23 (16)
C15—C20—C8—C9	3.2 (2)	C8—C7—C2—C1	−2.6 (2)
C19—C20—C8—C9	−178.44 (15)	C13—C12—N3—C22	−1.5 (3)
C15—C20—C8—C7	−124.42 (17)	C11—C12—N3—C22	−179.4 (2)
C19—C20—C8—C7	54.0 (2)	N2—N1—C1—O1	6.8 (3)
C14—O2—C15—C20	−2.7 (2)	C8—N1—C1—O1	172.78 (17)
C14—O2—C15—C16	178.35 (14)	N2—N1—C1—C2	−171.77 (15)
C19—C20—C15—O2	−179.92 (15)	C8—N1—C1—C2	−5.82 (19)
C8—C20—C15—O2	−1.5 (3)	C7—C2—C1—O1	−173.45 (19)
C19—C20—C15—C16	−1.0 (2)	C3—C2—C1—O1	6.6 (3)
C8—C20—C15—C16	177.45 (15)	C7—C2—C1—N1	5.1 (2)
C17—C16—C15—O2	179.53 (15)	C3—C2—C1—N1	−174.85 (19)
C17—C16—C15—C20	0.5 (3)	C2—C7—C6—C5	0.8 (3)
C9—C14—C13—C12	0.0 (3)	C8—C7—C6—C5	−177.00 (17)
O2—C14—C13—C12	−178.83 (15)	C7—C6—C5—C4	0.1 (3)
C15—C16—C17—N4	−177.69 (16)	C6—C5—C4—C3	−1.0 (3)
C15—C16—C17—C18	0.7 (3)	C5—C4—C3—C2	1.0 (3)
C15—C20—C19—C18	0.2 (3)	C7—C2—C3—C4	−0.1 (3)
C8—C20—C19—C18	−178.24 (16)	C1—C2—C3—C4	179.86 (19)
C9—C10—C11—C12	0.2 (3)	C12—N3—C22—C23	−79.0 (3)
C9—C10—C11—C21	177.93 (17)	C17—N4—C24—C25	177.3 (2)
C16—C17—N4—C24	0.3 (3)	N1—N2—C27—C28	178.42 (14)
C18—C17—N4—C24	−178.14 (19)	O3—C28—C27—N2	−60.6 (2)
N1—C8—C7—C6	177.36 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O3i	0.898 (16)	2.185 (18)	3.044 (2)	160 (2)
O3—H3C···O1ii	0.82	1.98	2.770 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O3i	0.898 (16)	2.185 (18)	3.044 (2)	160 (2)
O3—H3C⋯O1ii	0.82	1.98	2.770 (2)	162

Symmetry codes: (i) ; (ii) .