3',6'-Bis(diethyl-amino)-2-[(E)-2-(4-hy-droxy-3-meth-oxy-benzyl-idene-amino)-eth-yl]spiro-[isoindoline-1,9'-xanthen]-3-one ethanol monosolvate.

In the title compound, C(38)H(42)N(4)O(4)·C(2)H(6)O, prepared via a spiro-lactam ring-formation reaction in a rhodamine dye, the xanthene ring system is approximately planar (r.m.s. deviation = 0.0014Å) and subtends dihedral angles of 88.10 (3) and 86.92 (4)° with the spiro-lactam (r.m.s. deviations = 0.0012 Å) and benzene rings, respectively. The crystal structure consists of chains parallel to [-101], formed via O-H⋯O inter-actions.

Related literature

For related structures and background to rhodamine-based dyes, see: Xu et al.(2010a ▶,b ▶); Zhang et al. (2008 ▶); Tian & Peng (2008 ▶); Kwon et al. (2005 ▶); Wu et al.(2007 ▶).

Experimental

Crystal data

C38H42N4O4·C2H6O

M = 664.82

Monoclinic,

a = 16.674 (4) Å

b = 12.197 (3) Å

c = 17.936 (4) Å

β = 96.445 (4)°

V = 3624.5 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 113 K

0.20 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.984, T max = 0.992

45486 measured reflections

8576 independent reflections

7385 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.119

S = 1.10

8576 reflections

450 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812016741/bg2444sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016741/bg2444Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016741/bg2444Isup3.cml

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

C38H42N4O4·C2H6O	F(000) = 1424
Mr = 664.82	Dx = 1.218 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10662 reflections
a = 16.674 (4) Å	θ = 1.7–27.9°
b = 12.197 (3) Å	µ = 0.08 mm−1
c = 17.936 (4) Å	T = 113 K
β = 96.445 (4)°	Prism, colourless
V = 3624.5 (15) Å3	0.20 × 0.12 × 0.10 mm
Z = 4

Rigaku Saturn724+ diffractometer	8576 independent reflections
Radiation source: fine-focus sealed tube	7385 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 28.5714 pixels mm-1	θmax = 27.8°, θmin = 1.6°
profile data from ω–scans	h = −21→20
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −16→15
Tmin = 0.984, Tmax = 0.992	l = −23→22
45486 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0532P)2 + 0.5173P] where P = (Fo2 + 2Fc2)/3
8576 reflections	(Δ/σ)max < 0.001
450 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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 > 2sigma(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
O1	0.70816 (5)	0.41422 (7)	0.34461 (6)	0.0243 (2)
O2	0.45673 (6)	0.76065 (8)	0.19829 (5)	0.0257 (2)
O3	0.72460 (6)	0.76249 (8)	−0.25561 (5)	0.0281 (2)
H3	0.7427	0.7031	−0.2705	0.042*
O4	0.70162 (6)	0.56284 (8)	−0.19741 (5)	0.0284 (2)
N1	0.91108 (7)	0.68357 (10)	0.39924 (7)	0.0279 (3)
N2	0.53054 (7)	0.10821 (9)	0.31672 (7)	0.0238 (3)
N3	0.54525 (6)	0.62774 (9)	0.24766 (6)	0.0171 (2)
N4	0.66575 (7)	0.64858 (11)	0.08517 (7)	0.0296 (3)
C1	0.72358 (8)	0.52500 (10)	0.35283 (7)	0.0185 (3)
C2	0.80483 (8)	0.55002 (11)	0.37132 (7)	0.0210 (3)
H2	0.8432	0.4923	0.3787	0.025*
C3	0.83095 (8)	0.65951 (11)	0.37922 (7)	0.0217 (3)
C4	0.77103 (8)	0.74200 (11)	0.36664 (8)	0.0239 (3)
H4A	0.7862	0.8171	0.3700	0.029*
C5	0.69080 (8)	0.71404 (11)	0.34955 (7)	0.0215 (3)
H5	0.6519	0.7711	0.3423	0.026*
C6	0.66416 (7)	0.60495 (10)	0.34241 (7)	0.0171 (3)
C7	0.57572 (7)	0.57688 (10)	0.32152 (7)	0.0168 (3)
C8	0.56436 (7)	0.45356 (10)	0.31992 (7)	0.0172 (3)
C9	0.48720 (8)	0.40554 (11)	0.30829 (7)	0.0197 (3)
H9	0.4414	0.4522	0.3007	0.024*
C10	0.47538 (8)	0.29366 (11)	0.30742 (7)	0.0209 (3)
H10	0.4220	0.2653	0.2997	0.025*
C11	0.54168 (8)	0.22038 (10)	0.31793 (7)	0.0193 (3)
C12	0.61892 (8)	0.26706 (10)	0.32955 (7)	0.0200 (3)
H12	0.6650	0.2209	0.3368	0.024*
C13	0.62862 (7)	0.38069 (10)	0.33055 (7)	0.0181 (3)
C14	0.96754 (8)	0.59920 (12)	0.42960 (8)	0.0268 (3)
H14A	0.9384	0.5463	0.4586	0.032*
H14B	1.0101	0.6340	0.4648	0.032*
C15	1.00743 (9)	0.53699 (15)	0.37037 (9)	0.0380 (4)
H15A	0.9662	0.4977	0.3374	0.057*
H15B	1.0462	0.4843	0.3948	0.057*
H15C	1.0356	0.5888	0.3406	0.057*
C16	0.94234 (9)	0.79470 (13)	0.39605 (9)	0.0361 (4)
H16A	0.9114	0.8341	0.3540	0.043*
H16B	0.9993	0.7913	0.3855	0.043*
C17	0.93788 (13)	0.85921 (15)	0.46778 (11)	0.0575 (6)
H17A	0.8812	0.8693	0.4760	0.086*
H17B	0.9634	0.9310	0.4635	0.086*
H17C	0.9661	0.8190	0.5102	0.086*
C18	0.59972 (9)	0.03336 (11)	0.32402 (8)	0.0277 (3)
H18A	0.6422	0.0644	0.2959	0.033*
H18B	0.5826	−0.0373	0.3002	0.033*
C19	0.63582 (10)	0.01127 (14)	0.40393 (9)	0.0370 (4)
H19A	0.6489	0.0810	0.4296	0.055*
H19B	0.6851	−0.0324	0.4035	0.055*
H19C	0.5968	−0.0291	0.4304	0.055*
C20	0.45004 (9)	0.06076 (11)	0.31775 (8)	0.0270 (3)
H20A	0.4513	−0.0164	0.3007	0.032*
H20B	0.4117	0.1010	0.2815	0.032*
C21	0.41881 (10)	0.06364 (13)	0.39453 (9)	0.0366 (4)
H21A	0.4540	0.0192	0.4300	0.055*
H21B	0.3638	0.0340	0.3904	0.055*
H21C	0.4185	0.1395	0.4125	0.055*
C22	0.52088 (7)	0.63452 (10)	0.37207 (7)	0.0169 (3)
C23	0.51696 (8)	0.62006 (11)	0.44828 (7)	0.0216 (3)
H23	0.5518	0.5701	0.4767	0.026*
C24	0.46017 (9)	0.68132 (12)	0.48185 (8)	0.0261 (3)
H24	0.4563	0.6729	0.5340	0.031*
C25	0.40883 (8)	0.75484 (12)	0.44026 (8)	0.0263 (3)
H25	0.3702	0.7950	0.4643	0.032*
C26	0.41351 (8)	0.76991 (11)	0.36424 (8)	0.0228 (3)
H26	0.3791	0.8204	0.3358	0.027*
C27	0.47024 (7)	0.70856 (10)	0.33102 (7)	0.0181 (3)
C28	0.48748 (7)	0.70542 (10)	0.25194 (7)	0.0188 (3)
C29	0.57599 (8)	0.59905 (11)	0.17751 (7)	0.0216 (3)
H29A	0.5332	0.6123	0.1356	0.026*
H29B	0.5889	0.5198	0.1781	0.026*
C30	0.65106 (9)	0.66352 (14)	0.16326 (8)	0.0326 (4)
H30A	0.6431	0.7423	0.1735	0.039*
H30B	0.6982	0.6372	0.1971	0.039*
C31	0.67072 (8)	0.73611 (13)	0.04736 (8)	0.0269 (3)
H31	0.6655	0.8039	0.0724	0.032*
C32	0.68390 (8)	0.73984 (12)	−0.03207 (8)	0.0237 (3)
C33	0.69533 (9)	0.84087 (12)	−0.06541 (8)	0.0266 (3)
H33	0.6938	0.9060	−0.0366	0.032*
C34	0.70888 (8)	0.84776 (12)	−0.14018 (8)	0.0255 (3)
H34	0.7161	0.9172	−0.1624	0.031*
C35	0.71177 (8)	0.75289 (12)	−0.18223 (8)	0.0228 (3)
C36	0.69883 (8)	0.65032 (11)	−0.14962 (8)	0.0222 (3)
C37	0.68563 (8)	0.64348 (12)	−0.07481 (8)	0.0234 (3)
H37	0.6778	0.5741	−0.0526	0.028*
C38	0.67573 (10)	0.45925 (12)	−0.17106 (9)	0.0336 (4)
H38A	0.7124	0.4361	−0.1274	0.050*
H38B	0.6761	0.4045	−0.2110	0.050*
H38C	0.6209	0.4663	−0.1568	0.050*
O5	0.31286 (6)	0.87055 (9)	0.16462 (5)	0.0278 (2)
H5A	0.3581	0.8447	0.1812	0.042*
C39	0.29463 (9)	0.84136 (13)	0.08727 (8)	0.0290 (3)
H39A	0.3038	0.7619	0.0808	0.035*
H39B	0.3306	0.8819	0.0566	0.035*
C40	0.20807 (9)	0.86893 (15)	0.06150 (9)	0.0371 (4)
H40A	0.1727	0.8273	0.0912	0.056*
H40B	0.1959	0.8499	0.0084	0.056*
H40C	0.1993	0.9476	0.0682	0.056*

	U11	U22	U33	U12	U13	U23
O1	0.0147 (5)	0.0144 (5)	0.0434 (6)	−0.0003 (4)	0.0010 (4)	0.0004 (4)
O2	0.0234 (5)	0.0265 (5)	0.0263 (5)	0.0051 (4)	−0.0012 (4)	0.0095 (4)
O3	0.0307 (6)	0.0294 (6)	0.0247 (5)	0.0006 (4)	0.0055 (4)	0.0024 (4)
O4	0.0348 (6)	0.0240 (5)	0.0277 (5)	−0.0042 (4)	0.0088 (4)	−0.0042 (4)
N1	0.0187 (6)	0.0229 (6)	0.0401 (7)	−0.0045 (5)	−0.0060 (5)	0.0068 (5)
N2	0.0228 (6)	0.0165 (6)	0.0320 (7)	−0.0016 (5)	0.0029 (5)	−0.0009 (5)
N3	0.0175 (5)	0.0176 (5)	0.0158 (5)	0.0012 (4)	0.0009 (4)	0.0010 (4)
N4	0.0242 (6)	0.0417 (8)	0.0238 (6)	−0.0021 (5)	0.0067 (5)	−0.0018 (5)
C1	0.0188 (6)	0.0152 (6)	0.0214 (7)	−0.0003 (5)	0.0021 (5)	0.0024 (5)
C2	0.0175 (6)	0.0188 (6)	0.0263 (7)	0.0017 (5)	0.0005 (5)	0.0029 (5)
C3	0.0192 (7)	0.0223 (7)	0.0226 (7)	−0.0023 (5)	−0.0018 (5)	0.0033 (5)
C4	0.0241 (7)	0.0163 (6)	0.0297 (8)	−0.0033 (5)	−0.0039 (6)	0.0017 (5)
C5	0.0212 (7)	0.0174 (6)	0.0249 (7)	0.0023 (5)	−0.0019 (5)	0.0010 (5)
C6	0.0165 (6)	0.0177 (6)	0.0168 (6)	0.0002 (5)	0.0008 (5)	0.0010 (5)
C7	0.0162 (6)	0.0176 (6)	0.0162 (6)	0.0015 (5)	−0.0005 (5)	0.0023 (5)
C8	0.0182 (6)	0.0173 (6)	0.0160 (6)	0.0001 (5)	0.0016 (5)	0.0009 (5)
C9	0.0171 (6)	0.0202 (6)	0.0213 (7)	0.0019 (5)	−0.0004 (5)	0.0017 (5)
C10	0.0174 (6)	0.0211 (7)	0.0235 (7)	−0.0029 (5)	−0.0003 (5)	0.0000 (5)
C11	0.0236 (7)	0.0160 (6)	0.0186 (7)	−0.0016 (5)	0.0033 (5)	−0.0001 (5)
C12	0.0173 (6)	0.0167 (6)	0.0264 (7)	0.0025 (5)	0.0037 (5)	0.0004 (5)
C13	0.0151 (6)	0.0187 (6)	0.0205 (7)	−0.0008 (5)	0.0019 (5)	0.0004 (5)
C14	0.0183 (7)	0.0326 (8)	0.0282 (8)	−0.0019 (6)	−0.0029 (6)	0.0057 (6)
C15	0.0228 (8)	0.0558 (11)	0.0354 (9)	0.0019 (7)	0.0030 (7)	0.0001 (8)
C16	0.0276 (8)	0.0291 (8)	0.0482 (10)	−0.0131 (6)	−0.0102 (7)	0.0110 (7)
C17	0.0718 (14)	0.0336 (10)	0.0585 (12)	−0.0136 (9)	−0.0296 (10)	−0.0004 (9)
C18	0.0293 (8)	0.0163 (7)	0.0375 (8)	0.0002 (6)	0.0038 (6)	−0.0029 (6)
C19	0.0392 (9)	0.0311 (8)	0.0402 (9)	0.0072 (7)	0.0026 (7)	−0.0003 (7)
C20	0.0267 (7)	0.0185 (7)	0.0357 (8)	−0.0064 (6)	0.0037 (6)	−0.0004 (6)
C21	0.0364 (9)	0.0316 (9)	0.0440 (10)	−0.0022 (7)	0.0142 (7)	0.0034 (7)
C22	0.0150 (6)	0.0153 (6)	0.0202 (7)	−0.0015 (5)	0.0009 (5)	−0.0009 (5)
C23	0.0220 (7)	0.0223 (7)	0.0201 (7)	−0.0021 (5)	0.0005 (5)	0.0007 (5)
C24	0.0282 (8)	0.0307 (8)	0.0202 (7)	−0.0042 (6)	0.0068 (6)	−0.0033 (6)
C25	0.0225 (7)	0.0252 (7)	0.0324 (8)	0.0001 (6)	0.0084 (6)	−0.0069 (6)
C26	0.0172 (6)	0.0189 (7)	0.0323 (8)	0.0001 (5)	0.0026 (6)	−0.0005 (5)
C27	0.0153 (6)	0.0168 (6)	0.0220 (7)	−0.0020 (5)	0.0014 (5)	0.0004 (5)
C28	0.0143 (6)	0.0169 (6)	0.0244 (7)	−0.0020 (5)	−0.0004 (5)	0.0021 (5)
C29	0.0249 (7)	0.0219 (7)	0.0181 (7)	0.0006 (5)	0.0029 (5)	−0.0012 (5)
C30	0.0277 (8)	0.0497 (10)	0.0211 (7)	−0.0089 (7)	0.0060 (6)	−0.0027 (7)
C31	0.0218 (7)	0.0338 (8)	0.0254 (8)	−0.0055 (6)	0.0041 (6)	−0.0063 (6)
C32	0.0187 (7)	0.0281 (7)	0.0243 (7)	−0.0015 (5)	0.0025 (5)	−0.0015 (6)
C33	0.0268 (7)	0.0245 (7)	0.0290 (8)	0.0002 (6)	0.0049 (6)	−0.0054 (6)
C34	0.0242 (7)	0.0219 (7)	0.0304 (8)	0.0005 (6)	0.0031 (6)	0.0023 (6)
C35	0.0159 (6)	0.0293 (7)	0.0230 (7)	0.0008 (5)	0.0013 (5)	−0.0013 (6)
C36	0.0177 (6)	0.0246 (7)	0.0243 (7)	−0.0006 (5)	0.0023 (5)	−0.0034 (5)
C37	0.0201 (7)	0.0235 (7)	0.0269 (8)	−0.0023 (5)	0.0037 (6)	0.0010 (5)
C38	0.0377 (9)	0.0229 (7)	0.0413 (9)	−0.0045 (6)	0.0099 (7)	−0.0035 (6)
O5	0.0232 (5)	0.0368 (6)	0.0229 (5)	0.0051 (4)	−0.0004 (4)	0.0013 (4)
C39	0.0315 (8)	0.0323 (8)	0.0229 (7)	0.0023 (6)	0.0019 (6)	0.0018 (6)
C40	0.0296 (8)	0.0501 (10)	0.0300 (8)	−0.0048 (7)	−0.0039 (7)	0.0052 (7)

O1—C1	1.3802 (15)	C18—C19	1.515 (2)
O1—C13	1.3836 (15)	C18—H18A	0.9900
O2—C28	1.2376 (15)	C18—H18B	0.9900
O3—C35	1.3619 (17)	C19—H19A	0.9800
O3—H3	0.8400	C19—H19B	0.9800
O4—C36	1.3726 (16)	C19—H19C	0.9800
O4—C38	1.4324 (17)	C20—C21	1.527 (2)
N1—C3	1.3756 (17)	C20—H20A	0.9900
N1—C16	1.4556 (18)	C20—H20B	0.9900
N1—C14	1.4583 (18)	C21—H21A	0.9800
N2—C11	1.3805 (17)	C21—H21B	0.9800
N2—C20	1.4636 (18)	C21—H21C	0.9800
N2—C18	1.4653 (18)	C22—C23	1.3871 (18)
N3—C28	1.3593 (16)	C22—C27	1.3895 (18)
N3—C29	1.4537 (16)	C23—C24	1.3949 (19)
N3—C7	1.4989 (16)	C23—H23	0.9500
N4—C31	1.2724 (19)	C24—C25	1.396 (2)
N4—C30	1.4603 (18)	C24—H24	0.9500
C1—C6	1.3877 (18)	C25—C26	1.387 (2)
C1—C2	1.3919 (18)	C25—H25	0.9500
C2—C3	1.4068 (18)	C26—C27	1.3916 (18)
C2—H2	0.9500	C26—H26	0.9500
C3—C4	1.4180 (19)	C27—C28	1.4790 (18)
C4—C5	1.3812 (19)	C29—C30	1.524 (2)
C4—H4A	0.9500	C29—H29A	0.9900
C5—C6	1.4041 (18)	C29—H29B	0.9900
C5—H5	0.9500	C30—H30A	0.9900
C6—C7	1.5193 (17)	C30—H30B	0.9900
C7—C8	1.5159 (18)	C31—C32	1.466 (2)
C7—C22	1.5292 (17)	C31—H31	0.9500
C8—C13	1.3887 (18)	C32—C33	1.392 (2)
C8—C9	1.4077 (18)	C32—C37	1.4052 (19)
C9—C10	1.3786 (18)	C33—C34	1.387 (2)
C9—H9	0.9500	C33—H33	0.9500
C10—C11	1.4176 (19)	C34—C35	1.3851 (19)
C10—H10	0.9500	C34—H34	0.9500
C11—C12	1.4021 (18)	C35—C36	1.4078 (19)
C12—C13	1.3952 (18)	C36—C37	1.3865 (19)
C12—H12	0.9500	C37—H37	0.9500
C14—C15	1.518 (2)	C38—H38A	0.9800
C14—H14A	0.9900	C38—H38B	0.9800
C14—H14B	0.9900	C38—H38C	0.9800
C15—H15A	0.9800	O5—C39	1.4317 (17)
C15—H15B	0.9800	O5—H5A	0.8400
C15—H15C	0.9800	C39—C40	1.503 (2)
C16—C17	1.517 (3)	C39—H39A	0.9900
C16—H16A	0.9900	C39—H39B	0.9900
C16—H16B	0.9900	C40—H40A	0.9800
C17—H17A	0.9800	C40—H40B	0.9800
C17—H17B	0.9800	C40—H40C	0.9800
C17—H17C	0.9800
C1—O1—C13	118.17 (10)	C18—C19—H19C	109.5
C35—O3—H3	109.5	H19A—C19—H19C	109.5
C36—O4—C38	116.56 (11)	H19B—C19—H19C	109.5
C3—N1—C16	122.01 (12)	N2—C20—C21	114.11 (12)
C3—N1—C14	120.95 (12)	N2—C20—H20A	108.7
C16—N1—C14	116.92 (11)	C21—C20—H20A	108.7
C11—N2—C20	120.91 (11)	N2—C20—H20B	108.7
C11—N2—C18	120.85 (11)	C21—C20—H20B	108.7
C20—N2—C18	117.79 (11)	H20A—C20—H20B	107.6
C28—N3—C29	122.51 (11)	C20—C21—H21A	109.5
C28—N3—C7	114.25 (10)	C20—C21—H21B	109.5
C29—N3—C7	123.22 (10)	H21A—C21—H21B	109.5
C31—N4—C30	115.75 (13)	C20—C21—H21C	109.5
O1—C1—C6	123.49 (11)	H21A—C21—H21C	109.5
O1—C1—C2	113.88 (11)	H21B—C21—H21C	109.5
C6—C1—C2	122.62 (12)	C23—C22—C27	120.78 (12)
C1—C2—C3	120.94 (12)	C23—C22—C7	128.55 (11)
C1—C2—H2	119.5	C27—C22—C7	110.66 (11)
C3—C2—H2	119.5	C22—C23—C24	117.82 (13)
N1—C3—C2	120.63 (12)	C22—C23—H23	121.1
N1—C3—C4	122.44 (12)	C24—C23—H23	121.1
C2—C3—C4	116.92 (12)	C23—C24—C25	121.23 (13)
C5—C4—C3	120.51 (12)	C23—C24—H24	119.4
C5—C4—H4A	119.7	C25—C24—H24	119.4
C3—C4—H4A	119.7	C26—C25—C24	120.78 (13)
C4—C5—C6	122.88 (12)	C26—C25—H25	119.6
C4—C5—H5	118.6	C24—C25—H25	119.6
C6—C5—H5	118.6	C25—C26—C27	117.76 (12)
C1—C6—C5	116.09 (12)	C25—C26—H26	121.1
C1—C6—C7	122.24 (11)	C27—C26—H26	121.1
C5—C6—C7	121.63 (11)	C22—C27—C26	121.63 (12)
N3—C7—C8	111.39 (10)	C22—C27—C28	108.63 (11)
N3—C7—C6	110.37 (10)	C26—C27—C28	129.73 (12)
C8—C7—C6	110.12 (10)	O2—C28—N3	124.74 (12)
N3—C7—C22	99.66 (10)	O2—C28—C27	128.57 (12)
C8—C7—C22	112.68 (10)	N3—C28—C27	106.70 (11)
C6—C7—C22	112.25 (10)	N3—C29—C30	113.39 (11)
C13—C8—C9	115.62 (12)	N3—C29—H29A	108.9
C13—C8—C7	122.65 (11)	C30—C29—H29A	108.9
C9—C8—C7	121.73 (11)	N3—C29—H29B	108.9
C10—C9—C8	122.73 (12)	C30—C29—H29B	108.9
C10—C9—H9	118.6	H29A—C29—H29B	107.7
C8—C9—H9	118.6	N4—C30—C29	109.02 (12)
C9—C10—C11	120.95 (12)	N4—C30—H30A	109.9
C9—C10—H10	119.5	C29—C30—H30A	109.9
C11—C10—H10	119.5	N4—C30—H30B	109.9
N2—C11—C12	121.63 (12)	C29—C30—H30B	109.9
N2—C11—C10	121.41 (12)	H30A—C30—H30B	108.3
C12—C11—C10	116.95 (12)	N4—C31—C32	124.72 (14)
C13—C12—C11	120.57 (12)	N4—C31—H31	117.6
C13—C12—H12	119.7	C32—C31—H31	117.6
C11—C12—H12	119.7	C33—C32—C37	119.59 (13)
O1—C13—C8	123.02 (11)	C33—C32—C31	119.17 (13)
O1—C13—C12	113.79 (11)	C37—C32—C31	121.24 (13)
C8—C13—C12	123.18 (12)	C34—C33—C32	120.92 (13)
N1—C14—C15	113.99 (12)	C34—C33—H33	119.5
N1—C14—H14A	108.8	C32—C33—H33	119.5
C15—C14—H14A	108.8	C35—C34—C33	119.69 (13)
N1—C14—H14B	108.8	C35—C34—H34	120.2
C15—C14—H14B	108.8	C33—C34—H34	120.2
H14A—C14—H14B	107.6	O3—C35—C34	118.25 (13)
C14—C15—H15A	109.5	O3—C35—C36	121.73 (12)
C14—C15—H15B	109.5	C34—C35—C36	119.98 (13)
H15A—C15—H15B	109.5	O4—C36—C37	125.29 (13)
C14—C15—H15C	109.5	O4—C36—C35	114.45 (12)
H15A—C15—H15C	109.5	C37—C36—C35	120.26 (12)
H15B—C15—H15C	109.5	C36—C37—C32	119.53 (13)
N1—C16—C17	113.44 (14)	C36—C37—H37	120.2
N1—C16—H16A	108.9	C32—C37—H37	120.2
C17—C16—H16A	108.9	O4—C38—H38A	109.5
N1—C16—H16B	108.9	O4—C38—H38B	109.5
C17—C16—H16B	108.9	H38A—C38—H38B	109.5
H16A—C16—H16B	107.7	O4—C38—H38C	109.5
C16—C17—H17A	109.5	H38A—C38—H38C	109.5
C16—C17—H17B	109.5	H38B—C38—H38C	109.5
H17A—C17—H17B	109.5	C39—O5—H5A	109.5
C16—C17—H17C	109.5	O5—C39—C40	109.53 (12)
H17A—C17—H17C	109.5	O5—C39—H39A	109.8
H17B—C17—H17C	109.5	C40—C39—H39A	109.8
N2—C18—C19	114.87 (12)	O5—C39—H39B	109.8
N2—C18—H18A	108.6	C40—C39—H39B	109.8
C19—C18—H18A	108.6	H39A—C39—H39B	108.2
N2—C18—H18B	108.6	C39—C40—H40A	109.5
C19—C18—H18B	108.6	C39—C40—H40B	109.5
H18A—C18—H18B	107.5	H40A—C40—H40B	109.5
C18—C19—H19A	109.5	C39—C40—H40C	109.5
C18—C19—H19B	109.5	H40A—C40—H40C	109.5
H19A—C19—H19B	109.5	H40B—C40—H40C	109.5
C13—O1—C1—C6	−4.83 (18)	C3—N1—C14—C15	89.30 (16)
C13—O1—C1—C2	176.30 (11)	C16—N1—C14—C15	−94.71 (16)
O1—C1—C2—C3	177.85 (11)	C3—N1—C16—C17	88.72 (18)
C6—C1—C2—C3	−1.0 (2)	C14—N1—C16—C17	−87.22 (17)
C16—N1—C3—C2	169.76 (13)	C11—N2—C18—C19	83.16 (16)
C14—N1—C3—C2	−14.5 (2)	C20—N2—C18—C19	−89.23 (16)
C16—N1—C3—C4	−11.1 (2)	C11—N2—C20—C21	−76.12 (16)
C14—N1—C3—C4	164.66 (13)	C18—N2—C20—C21	96.26 (15)
C1—C2—C3—N1	178.44 (12)	N3—C7—C22—C23	177.55 (12)
C1—C2—C3—C4	−0.7 (2)	C8—C7—C22—C23	59.38 (17)
N1—C3—C4—C5	−177.39 (13)	C6—C7—C22—C23	−65.64 (17)
C2—C3—C4—C5	1.8 (2)	N3—C7—C22—C27	−1.82 (13)
C3—C4—C5—C6	−1.1 (2)	C8—C7—C22—C27	−119.99 (12)
O1—C1—C6—C5	−177.09 (12)	C6—C7—C22—C27	114.99 (12)
C2—C1—C6—C5	1.68 (19)	C27—C22—C23—C24	0.62 (19)
O1—C1—C6—C7	0.63 (19)	C7—C22—C23—C24	−178.69 (12)
C2—C1—C6—C7	179.41 (12)	C22—C23—C24—C25	0.0 (2)
C4—C5—C6—C1	−0.6 (2)	C23—C24—C25—C26	−0.7 (2)
C4—C5—C6—C7	−178.35 (12)	C24—C25—C26—C27	0.7 (2)
C28—N3—C7—C8	122.41 (12)	C23—C22—C27—C26	−0.62 (19)
C29—N3—C7—C8	−59.14 (15)	C7—C22—C27—C26	178.81 (11)
C28—N3—C7—C6	−114.94 (12)	C23—C22—C27—C28	−179.42 (11)
C29—N3—C7—C6	63.51 (15)	C7—C22—C27—C28	0.01 (14)
C28—N3—C7—C22	3.28 (13)	C25—C26—C27—C22	−0.06 (19)
C29—N3—C7—C22	−178.27 (11)	C25—C26—C27—C28	178.47 (13)
C1—C6—C7—N3	−119.49 (13)	C29—N3—C28—O2	−1.7 (2)
C5—C6—C7—N3	58.12 (15)	C7—N3—C28—O2	176.80 (12)
C1—C6—C7—C8	3.90 (16)	C29—N3—C28—C27	178.09 (11)
C5—C6—C7—C8	−178.50 (11)	C7—N3—C28—C27	−3.45 (14)
C1—C6—C7—C22	130.32 (13)	C22—C27—C28—O2	−178.20 (13)
C5—C6—C7—C22	−52.08 (16)	C26—C27—C28—O2	3.1 (2)
N3—C7—C8—C13	118.10 (13)	C22—C27—C28—N3	2.06 (14)
C6—C7—C8—C13	−4.69 (16)	C26—C27—C28—N3	−176.62 (13)
C22—C7—C8—C13	−130.87 (12)	C28—N3—C29—C30	92.73 (15)
N3—C7—C8—C9	−62.64 (15)	C7—N3—C29—C30	−85.59 (15)
C6—C7—C8—C9	174.57 (11)	C31—N4—C30—C29	124.69 (14)
C22—C7—C8—C9	48.40 (16)	N3—C29—C30—N4	−166.68 (12)
C13—C8—C9—C10	0.04 (19)	C30—N4—C31—C32	−178.98 (12)
C7—C8—C9—C10	−179.27 (12)	N4—C31—C32—C33	−174.37 (14)
C8—C9—C10—C11	−0.4 (2)	N4—C31—C32—C37	5.3 (2)
C20—N2—C11—C12	169.20 (12)	C37—C32—C33—C34	−0.4 (2)
C18—N2—C11—C12	−3.0 (2)	C31—C32—C33—C34	179.27 (12)
C20—N2—C11—C10	−10.84 (19)	C32—C33—C34—C35	−0.5 (2)
C18—N2—C11—C10	177.01 (12)	C33—C34—C35—O3	179.54 (12)
C9—C10—C11—N2	−179.60 (12)	C33—C34—C35—C36	1.7 (2)
C9—C10—C11—C12	0.36 (19)	C38—O4—C36—C37	10.84 (19)
N2—C11—C12—C13	−179.99 (12)	C38—O4—C36—C35	−169.93 (12)
C10—C11—C12—C13	0.04 (19)	O3—C35—C36—O4	0.98 (18)
C1—O1—C13—C8	3.99 (18)	C34—C35—C36—O4	178.74 (12)
C1—O1—C13—C12	−174.79 (11)	O3—C35—C36—C37	−179.74 (12)
C9—C8—C13—O1	−178.28 (12)	C34—C35—C36—C37	−2.0 (2)
C7—C8—C13—O1	1.02 (19)	O4—C36—C37—C32	−179.74 (12)
C9—C8—C13—C12	0.38 (19)	C35—C36—C37—C32	1.1 (2)
C7—C8—C13—C12	179.69 (12)	C33—C32—C37—C36	0.1 (2)
C11—C12—C13—O1	178.35 (11)	C31—C32—C37—C36	−179.54 (12)
C11—C12—C13—C8	−0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5i	0.84	1.96	2.7052 (15)	148
O5—H5A···O2	0.84	1.93	2.7552 (14)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O5i	0.84	1.96	2.7052 (15)	148
O5—H5A⋯O2	0.84	1.93	2.7552 (14)	166

Symmetry code: (i) .