3,6-Dihydr-oxy-2'-[(2-hydr-oxy-1-naphth-yl)methyl-eneamino]xanthene-9-spiro-1'-isoindolin-3'-one acetonitrile solvate.

The title compound, C(31)H(20)N(2)O(5)·C(2)H(3)N, was synthesized by the reaction of fluorescein hydrazide and excess 2-hydr-oxy-1-naphthaldehyde in acetonitrile. The spirolactam ring is planar and is nearly at right angles to the two benzene rings of the xanthene system. The dihedral angle between the two benzene rings of the xanthene system is 9.92 (4)°. In the crystal structure, the mol-ecules are linked into extended two-dimensional networks by inter-molecular hydrogen bonding. Acetonitrile mol-ecules are located in the voids between the two-dimensional networks.

Related literature

For general background, see: Chen et al., (2006 ▶). For related literature, see: Wu et al., (2007 ▶).

Experimental

Crystal data

C31H20N2O5·C2H3N

M = 541.54

Monoclinic,

a = 18.729 (5) Å

b = 15.572 (4) Å

c = 9.021 (2) Å

β = 98.495 (4)°

V = 2601.9 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.26 × 0.22 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.976, T max = 0.985

12963 measured reflections

4627 independent reflections

3272 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.03

4627 reflections

375 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT-Plus (Bruker, 1997 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Bruker, 2000 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808000974/at2535sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000974/at2535Isup2.hkl

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

C31H20N2O5·C2H3N	F000 = 1128
Mr = 541.54	Dx = 1.382 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4034 reflections
a = 18.729 (5) Å	θ = 2.4–27.0º
b = 15.572 (4) Å	µ = 0.10 mm−1
c = 9.021 (2) Å	T = 293 (2) K
β = 98.495 (4)º	Block, yellow
V = 2601.9 (11) Å3	0.26 × 0.22 × 0.16 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	4627 independent reflections
Radiation source: sealed tube	3272 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
T = 293(2) K	θmax = 25.1º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)	h = −22→20
Tmin = 0.976, Tmax = 0.985	k = −17→18
12963 measured reflections	l = −10→10

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037	w = 1/[σ2(Fo2) + (0.0455P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.14 e Å−3
4627 reflections	Δρmin = −0.15 e Å−3
375 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0070 (7)
Secondary atom site location: difference Fourier map

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 > σ(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
C1	0.33564 (7)	0.42174 (9)	0.79315 (17)	0.0395 (4)
C2	0.35217 (9)	0.33479 (10)	0.7884 (2)	0.0545 (4)
H2	0.3272	0.3011	0.7128	0.065*
C3	0.40416 (9)	0.29689 (10)	0.8916 (2)	0.0574 (5)
H7	0.4137	0.2385	0.8861	0.069*
C4	0.44199 (8)	0.34666 (10)	1.00373 (18)	0.0457 (4)
C5	0.42780 (8)	0.43291 (9)	1.01071 (17)	0.0425 (4)
H5	0.4536	0.4667	1.0851	0.051*
C6	0.37473 (7)	0.46933 (9)	0.90608 (16)	0.0394 (4)
C7	0.31973 (8)	0.59927 (9)	0.81305 (17)	0.0419 (4)
C8	0.32082 (8)	0.68757 (10)	0.82713 (18)	0.0480 (4)
H8	0.3494	0.7135	0.9078	0.058*
C9	0.27929 (8)	0.73684 (10)	0.72100 (19)	0.0479 (4)
C10	0.23642 (8)	0.69775 (10)	0.60184 (19)	0.0533 (4)
H10	0.2083	0.7308	0.5297	0.064*
C11	0.23580 (8)	0.60990 (10)	0.59104 (19)	0.0504 (4)
H11	0.2067	0.5842	0.5108	0.060*
C12	0.27727 (7)	0.55775 (9)	0.69603 (17)	0.0405 (4)
C13	0.27427 (7)	0.46102 (9)	0.68603 (16)	0.0396 (4)
C14	0.26945 (8)	0.42604 (9)	0.52772 (17)	0.0437 (4)
C15	0.31751 (9)	0.43535 (11)	0.4270 (2)	0.0594 (5)
H15	0.3601	0.4662	0.4521	0.071*
C16	0.30051 (11)	0.39730 (12)	0.2870 (2)	0.0693 (5)
H16	0.3318	0.4039	0.2169	0.083*
C17	0.23812 (11)	0.34980 (12)	0.2495 (2)	0.0635 (5)
H17	0.2284	0.3243	0.1555	0.076*
C18	0.19056 (9)	0.34007 (10)	0.34988 (18)	0.0548 (4)
H18	0.1486	0.3079	0.3256	0.066*
C19	0.20660 (8)	0.37939 (9)	0.48858 (17)	0.0436 (4)
C20	0.16357 (8)	0.38148 (10)	0.61280 (17)	0.0448 (4)
C21	0.13128 (7)	0.42358 (9)	0.91136 (17)	0.0408 (4)
H21	0.1084	0.3753	0.8659	0.049*
C22	0.10663 (7)	0.46010 (9)	1.04201 (16)	0.0396 (4)
C23	0.13326 (8)	0.53795 (10)	1.10112 (17)	0.0462 (4)
C24	0.10413 (10)	0.57803 (12)	1.21788 (19)	0.0598 (5)
H24	0.1220	0.6309	1.2540	0.072*
C25	0.05010 (10)	0.54010 (13)	1.27822 (19)	0.0622 (5)
H25	0.0308	0.5679	1.3544	0.075*
C26	0.02242 (8)	0.45900 (11)	1.22770 (18)	0.0518 (4)
C27	−0.03305 (9)	0.41847 (14)	1.2928 (2)	0.0682 (5)
H27	−0.0526	0.4462	1.3689	0.082*
C28	−0.05798 (11)	0.34026 (15)	1.2463 (2)	0.0771 (6)
H28	−0.0945	0.3143	1.2900	0.093*
C29	−0.02859 (9)	0.29812 (13)	1.1316 (2)	0.0708 (5)
H29	−0.0452	0.2437	1.1010	0.085*
C30	0.02372 (8)	0.33577 (11)	1.06483 (19)	0.0548 (4)
H30	0.0421	0.3069	0.9884	0.066*
C31	0.05084 (7)	0.41780 (10)	1.10902 (17)	0.0431 (4)
C32	0.54315 (12)	0.38827 (12)	0.6728 (2)	0.0826 (6)
H32A	0.5930	0.3955	0.7141	0.124*
H32B	0.5265	0.3336	0.7028	0.124*
H32C	0.5151	0.4332	0.7087	0.124*
C33	0.53548 (10)	0.39211 (12)	0.5109 (3)	0.0678 (5)
N1	0.18474 (6)	0.45736 (8)	0.85739 (13)	0.0403 (3)
N2	0.20397 (6)	0.42793 (7)	0.72513 (13)	0.0404 (3)
N3	0.52922 (10)	0.39621 (12)	0.3840 (2)	0.0900 (6)
O1	0.28347 (6)	0.82387 (7)	0.73845 (14)	0.0670 (4)
H1	0.2542	0.8470	0.6743	0.100*
O2	0.36425 (6)	0.55596 (6)	0.92433 (12)	0.0537 (3)
O3	0.49339 (6)	0.30663 (7)	1.10332 (14)	0.0644 (4)
H6	0.5067	0.3389	1.1738	0.097*
O4	0.18721 (6)	0.58052 (7)	1.04607 (13)	0.0589 (3)
H4	0.1992	0.5533	0.9759	0.088*
O5	0.10443 (6)	0.35036 (8)	0.61789 (13)	0.0678 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0349 (8)	0.0383 (9)	0.0458 (9)	−0.0024 (6)	0.0074 (7)	0.0024 (7)
C2	0.0552 (10)	0.0407 (10)	0.0634 (11)	−0.0034 (8)	−0.0047 (9)	−0.0041 (8)
C3	0.0630 (11)	0.0349 (9)	0.0695 (12)	0.0048 (8)	−0.0057 (9)	−0.0008 (8)
C4	0.0447 (9)	0.0421 (9)	0.0497 (10)	0.0035 (7)	0.0053 (8)	0.0050 (7)
C5	0.0452 (9)	0.0405 (9)	0.0407 (9)	−0.0021 (7)	0.0024 (7)	−0.0003 (7)
C6	0.0427 (9)	0.0329 (8)	0.0436 (9)	0.0006 (6)	0.0099 (7)	0.0016 (7)
C7	0.0416 (9)	0.0408 (9)	0.0432 (9)	0.0053 (7)	0.0059 (7)	0.0061 (7)
C8	0.0501 (9)	0.0400 (9)	0.0524 (10)	0.0037 (7)	0.0025 (8)	−0.0007 (7)
C9	0.0491 (10)	0.0381 (9)	0.0575 (11)	0.0055 (7)	0.0115 (8)	0.0073 (8)
C10	0.0489 (10)	0.0502 (11)	0.0593 (11)	0.0057 (8)	0.0032 (9)	0.0163 (8)
C11	0.0435 (9)	0.0520 (11)	0.0534 (11)	−0.0026 (7)	−0.0004 (8)	0.0077 (8)
C12	0.0353 (8)	0.0411 (9)	0.0459 (9)	−0.0010 (6)	0.0090 (7)	0.0047 (7)
C13	0.0345 (8)	0.0429 (9)	0.0419 (9)	−0.0031 (6)	0.0077 (7)	0.0020 (7)
C14	0.0431 (9)	0.0453 (9)	0.0428 (9)	0.0058 (7)	0.0067 (7)	0.0032 (7)
C15	0.0573 (10)	0.0682 (12)	0.0561 (12)	0.0001 (9)	0.0196 (9)	0.0022 (9)
C16	0.0804 (14)	0.0795 (14)	0.0530 (12)	0.0217 (11)	0.0267 (11)	0.0086 (10)
C17	0.0785 (13)	0.0681 (12)	0.0422 (11)	0.0274 (10)	0.0039 (10)	−0.0020 (9)
C18	0.0604 (11)	0.0537 (11)	0.0466 (10)	0.0122 (8)	−0.0037 (9)	−0.0050 (8)
C19	0.0459 (9)	0.0440 (9)	0.0396 (9)	0.0055 (7)	0.0020 (7)	0.0014 (7)
C20	0.0419 (9)	0.0451 (9)	0.0459 (10)	−0.0040 (7)	0.0017 (7)	−0.0033 (7)
C21	0.0386 (8)	0.0379 (8)	0.0457 (9)	−0.0019 (7)	0.0052 (7)	0.0007 (7)
C22	0.0364 (8)	0.0437 (9)	0.0376 (9)	0.0050 (7)	0.0018 (7)	0.0039 (7)
C23	0.0454 (9)	0.0509 (10)	0.0413 (9)	0.0020 (7)	0.0028 (7)	−0.0011 (7)
C24	0.0641 (11)	0.0649 (12)	0.0489 (11)	0.0051 (9)	0.0039 (9)	−0.0121 (9)
C25	0.0634 (11)	0.0820 (14)	0.0417 (10)	0.0176 (10)	0.0092 (9)	−0.0053 (9)
C26	0.0462 (9)	0.0688 (12)	0.0410 (10)	0.0137 (8)	0.0081 (8)	0.0133 (8)
C27	0.0582 (11)	0.0988 (16)	0.0508 (11)	0.0168 (11)	0.0188 (9)	0.0190 (11)
C28	0.0636 (12)	0.0927 (17)	0.0803 (15)	−0.0013 (11)	0.0278 (11)	0.0310 (12)
C29	0.0632 (12)	0.0694 (13)	0.0838 (14)	−0.0063 (10)	0.0240 (11)	0.0190 (11)
C30	0.0503 (10)	0.0556 (11)	0.0611 (11)	0.0010 (8)	0.0166 (9)	0.0118 (9)
C31	0.0378 (8)	0.0511 (10)	0.0398 (9)	0.0096 (7)	0.0040 (7)	0.0103 (7)
C32	0.1057 (17)	0.0644 (13)	0.0762 (15)	−0.0114 (11)	0.0088 (13)	−0.0104 (11)
C33	0.0679 (13)	0.0562 (12)	0.0775 (16)	−0.0092 (9)	0.0048 (12)	−0.0128 (11)
N1	0.0388 (7)	0.0432 (7)	0.0389 (7)	−0.0020 (5)	0.0059 (6)	−0.0012 (6)
N2	0.0366 (7)	0.0449 (7)	0.0399 (7)	−0.0070 (5)	0.0068 (6)	−0.0054 (6)
N3	0.0966 (14)	0.0927 (14)	0.0773 (13)	−0.0082 (10)	0.0014 (12)	−0.0090 (11)
O1	0.0785 (9)	0.0400 (7)	0.0783 (9)	0.0095 (6)	−0.0022 (7)	0.0083 (6)
O2	0.0680 (7)	0.0367 (6)	0.0509 (7)	0.0085 (5)	−0.0094 (6)	−0.0027 (5)
O3	0.0701 (8)	0.0492 (7)	0.0668 (8)	0.0141 (6)	−0.0135 (7)	0.0053 (6)
O4	0.0616 (7)	0.0571 (7)	0.0596 (8)	−0.0153 (6)	0.0145 (6)	−0.0149 (6)
O5	0.0510 (7)	0.0878 (9)	0.0651 (8)	−0.0290 (6)	0.0100 (6)	−0.0191 (7)

C1—C6	1.379 (2)	C18—H18	0.9300
C1—C2	1.391 (2)	C19—C20	1.474 (2)
C1—C13	1.5168 (19)	C20—O5	1.2161 (17)
C2—C3	1.377 (2)	C20—N2	1.3769 (18)
C2—H2	0.9300	C21—N1	1.2885 (17)
C3—C4	1.383 (2)	C21—C22	1.444 (2)
C3—H7	0.9300	C21—H21	0.9300
C4—C5	1.372 (2)	C22—C23	1.387 (2)
C4—O3	1.3663 (18)	C22—C31	1.441 (2)
C5—C6	1.3867 (19)	C23—O4	1.3620 (18)
C5—H5	0.9300	C23—C24	1.402 (2)
C6—O2	1.3767 (17)	C24—C25	1.353 (2)
C7—C8	1.381 (2)	C24—H24	0.9300
C7—O2	1.3821 (17)	C25—C26	1.415 (2)
C7—C12	1.384 (2)	C25—H25	0.9300
C8—C9	1.375 (2)	C26—C31	1.418 (2)
C8—H8	0.9300	C26—C27	1.415 (2)
C9—O1	1.3652 (18)	C27—C28	1.349 (3)
C9—C10	1.384 (2)	C27—H27	0.9300
C10—C11	1.371 (2)	C28—C29	1.404 (3)
C10—H10	0.9300	C28—H28	0.9300
C11—C12	1.394 (2)	C29—C30	1.357 (2)
C11—H11	0.9300	C29—H29	0.9300
C12—C13	1.510 (2)	C30—C31	1.410 (2)
C13—N2	1.5036 (17)	C30—H30	0.9300
C13—C14	1.519 (2)	C32—C33	1.447 (3)
C14—C15	1.378 (2)	C32—H32A	0.9600
C14—C19	1.384 (2)	C32—H32B	0.9600
C15—C16	1.389 (3)	C32—H32C	0.9600
C15—H15	0.9300	C33—N3	1.135 (2)
C16—C17	1.382 (3)	N1—N2	1.3747 (16)
C16—H16	0.9300	O1—H1	0.8200
C17—C18	1.369 (2)	O3—H6	0.8200
C17—H17	0.9300	O4—H4	0.8200
C18—C19	1.385 (2)
C6—C1—C2	116.72 (13)	C19—C18—H18	120.9
C6—C1—C13	121.57 (13)	C18—C19—C14	121.68 (15)
C2—C1—C13	121.59 (13)	C18—C19—C20	128.78 (15)
C3—C2—C1	122.31 (15)	C14—C19—C20	109.53 (13)
C3—C2—H2	118.8	O5—C20—N2	125.88 (14)
C1—C2—H2	118.8	O5—C20—C19	128.55 (14)
C2—C3—C4	119.27 (15)	N2—C20—C19	105.57 (13)
C2—C3—H7	120.4	N1—C21—C22	120.49 (14)
C4—C3—H7	120.4	N1—C21—H21	119.8
C5—C4—O3	122.60 (14)	C22—C21—H21	119.8
C5—C4—C3	120.01 (14)	C23—C22—C31	118.68 (14)
O3—C4—C3	117.39 (14)	C23—C22—C21	121.17 (14)
C4—C5—C6	119.55 (14)	C31—C22—C21	120.08 (14)
C4—C5—H5	120.2	O4—C23—C22	121.95 (14)
C6—C5—H5	120.2	O4—C23—C24	116.69 (15)
O2—C6—C1	123.04 (13)	C22—C23—C24	121.33 (15)
O2—C6—C5	114.82 (13)	C25—C24—C23	120.32 (17)
C1—C6—C5	122.14 (14)	C25—C24—H24	119.8
C8—C7—O2	114.83 (13)	C23—C24—H24	119.8
C8—C7—C12	122.28 (14)	C24—C25—C26	121.34 (16)
O2—C7—C12	122.88 (14)	C24—C25—H25	119.3
C9—C8—C7	119.51 (15)	C26—C25—H25	119.3
C9—C8—H8	120.2	C31—C26—C27	119.49 (17)
C7—C8—H8	120.2	C31—C26—C25	119.12 (15)
O1—C9—C8	117.18 (15)	C27—C26—C25	121.39 (17)
O1—C9—C10	122.88 (14)	C28—C27—C26	120.99 (18)
C8—C9—C10	119.93 (15)	C28—C27—H27	119.5
C11—C10—C9	119.46 (15)	C26—C27—H27	119.5
C11—C10—H10	120.3	C27—C28—C29	119.73 (17)
C9—C10—H10	120.3	C27—C28—H28	120.1
C10—C11—C12	122.34 (15)	C29—C28—H28	120.1
C10—C11—H11	118.8	C30—C29—C28	120.82 (19)
C12—C11—H11	118.8	C30—C29—H29	119.6
C7—C12—C11	116.47 (14)	C28—C29—H29	119.6
C7—C12—C13	121.57 (13)	C29—C30—C31	121.30 (17)
C11—C12—C13	121.93 (13)	C29—C30—H30	119.3
N2—C13—C12	110.73 (11)	C31—C30—H30	119.3
N2—C13—C1	108.65 (11)	C26—C31—C30	117.62 (14)
C12—C13—C1	110.26 (12)	C26—C31—C22	119.09 (15)
N2—C13—C14	99.51 (11)	C30—C31—C22	123.27 (14)
C12—C13—C14	114.24 (12)	C33—C32—H32A	109.5
C1—C13—C14	112.87 (12)	C33—C32—H32B	109.5
C15—C14—C19	120.07 (15)	H32A—C32—H32B	109.5
C15—C14—C13	128.93 (14)	C33—C32—H32C	109.5
C19—C14—C13	111.00 (13)	H32A—C32—H32C	109.5
C14—C15—C16	118.06 (17)	H32B—C32—H32C	109.5
C14—C15—H15	121.0	N3—C33—C32	179.1 (2)
C16—C15—H15	121.0	C21—N1—N2	120.63 (12)
C17—C16—C15	121.52 (17)	N1—N2—C20	128.89 (12)
C17—C16—H16	119.2	N1—N2—C13	116.11 (11)
C15—C16—H16	119.2	C20—N2—C13	114.35 (12)
C18—C17—C16	120.44 (17)	C9—O1—H1	109.5
C18—C17—H17	119.8	C6—O2—C7	118.21 (11)
C16—C17—H17	119.8	C4—O3—H6	109.5
C17—C18—C19	118.22 (17)	C23—O4—H4	109.5
C17—C18—H18	120.9
C6—C1—C2—C3	0.8 (2)	C15—C14—C19—C18	0.9 (2)
C13—C1—C2—C3	−175.13 (15)	C13—C14—C19—C18	−179.13 (13)
C1—C2—C3—C4	−0.6 (3)	C15—C14—C19—C20	−178.10 (14)
C2—C3—C4—C5	−0.3 (2)	C13—C14—C19—C20	1.88 (17)
C2—C3—C4—O3	−179.62 (15)	C18—C19—C20—O5	−1.5 (3)
O3—C4—C5—C6	−179.86 (14)	C14—C19—C20—O5	177.43 (16)
C3—C4—C5—C6	0.9 (2)	C18—C19—C20—N2	179.33 (15)
C2—C1—C6—O2	179.93 (13)	C14—C19—C20—N2	−1.77 (17)
C13—C1—C6—O2	−4.1 (2)	N1—C21—C22—C23	8.3 (2)
C2—C1—C6—C5	−0.3 (2)	N1—C21—C22—C31	−174.81 (12)
C13—C1—C6—C5	175.71 (13)	C31—C22—C23—O4	178.31 (13)
C4—C5—C6—O2	179.24 (13)	C21—C22—C23—O4	−4.7 (2)
C4—C5—C6—C1	−0.6 (2)	C31—C22—C23—C24	−3.8 (2)
O2—C7—C8—C9	179.00 (13)	C21—C22—C23—C24	173.18 (13)
C12—C7—C8—C9	−0.9 (2)	O4—C23—C24—C25	179.68 (15)
C7—C8—C9—O1	−178.66 (14)	C22—C23—C24—C25	1.6 (3)
C7—C8—C9—C10	0.5 (2)	C23—C24—C25—C26	1.1 (3)
O1—C9—C10—C11	179.17 (15)	C24—C25—C26—C31	−1.5 (2)
C8—C9—C10—C11	0.1 (2)	C24—C25—C26—C27	178.67 (16)
C9—C10—C11—C12	−0.3 (2)	C31—C26—C27—C28	1.7 (3)
C8—C7—C12—C11	0.7 (2)	C25—C26—C27—C28	−178.46 (17)
O2—C7—C12—C11	−179.20 (13)	C26—C27—C28—C29	0.0 (3)
C8—C7—C12—C13	−177.30 (14)	C27—C28—C29—C30	−1.3 (3)
O2—C7—C12—C13	2.8 (2)	C28—C29—C30—C31	0.7 (3)
C10—C11—C12—C7	−0.1 (2)	C27—C26—C31—C30	−2.2 (2)
C10—C11—C12—C13	177.87 (14)	C25—C26—C31—C30	177.93 (14)
C7—C12—C13—N2	106.04 (15)	C27—C26—C31—C22	179.15 (13)
C11—C12—C13—N2	−71.84 (17)	C25—C26—C31—C22	−0.7 (2)
C7—C12—C13—C1	−14.24 (18)	C29—C30—C31—C26	1.1 (2)
C11—C12—C13—C1	167.88 (13)	C29—C30—C31—C22	179.63 (15)
C7—C12—C13—C14	−142.61 (14)	C23—C22—C31—C26	3.2 (2)
C11—C12—C13—C14	39.52 (19)	C21—C22—C31—C26	−173.75 (13)
C6—C1—C13—N2	−106.63 (15)	C23—C22—C31—C30	−175.28 (14)
C2—C1—C13—N2	69.15 (17)	C21—C22—C31—C30	7.7 (2)
C6—C1—C13—C12	14.90 (18)	C22—C21—N1—N2	−173.76 (12)
C2—C1—C13—C12	−169.33 (13)	C21—N1—N2—C20	19.9 (2)
C6—C1—C13—C14	144.01 (14)	C21—N1—N2—C13	−169.86 (12)
C2—C1—C13—C14	−40.22 (19)	O5—C20—N2—N1	−7.9 (3)
N2—C13—C14—C15	178.80 (15)	C19—C20—N2—N1	171.36 (13)
C12—C13—C14—C15	60.8 (2)	O5—C20—N2—C13	−178.20 (15)
C1—C13—C14—C15	−66.2 (2)	C19—C20—N2—C13	1.02 (16)
N2—C13—C14—C19	−1.18 (15)	C12—C13—N2—N1	−51.04 (16)
C12—C13—C14—C19	−119.14 (14)	C1—C13—N2—N1	70.20 (15)
C1—C13—C14—C19	113.83 (14)	C14—C13—N2—N1	−171.60 (11)
C19—C14—C15—C16	0.4 (2)	C12—C13—N2—C20	120.60 (14)
C13—C14—C15—C16	−179.55 (15)	C1—C13—N2—C20	−118.17 (14)
C14—C15—C16—C17	−1.3 (3)	C14—C13—N2—C20	0.03 (15)
C15—C16—C17—C18	1.0 (3)	C1—C6—O2—C7	−9.1 (2)
C16—C17—C18—C19	0.3 (2)	C5—C6—O2—C7	171.10 (12)
C17—C18—C19—C14	−1.3 (2)	C8—C7—O2—C6	−170.15 (13)
C17—C18—C19—C20	177.50 (15)	C12—C7—O2—C6	9.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N1	0.82	1.83	2.5600 (16)	147
O3—H6···N3i	0.82	2.08	2.882 (2)	165
O1—H1···O4ii	0.82	1.94	2.7484 (16)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯N1	0.82	1.83	2.5600 (16)	147
O3—H6⋯N3i	0.82	2.08	2.882 (2)	165
O1—H1⋯O4ii	0.82	1.94	2.7484 (16)	170

Symmetry codes: (i) ; (ii) .