2-[(E)-(2-Hy-droxy-naphthalen-1-yl)methyl-idene-amino]-isoindoline-1,3-dione.

The title compound, C(19)H(12)N(2)O(3), has two independent mol-ecules (A and B) in the asymmetric unit. There is an intra-molecular O-H⋯N hydrogen bond in each mol-ecule. The mean planes of the naphthalene [maximum deviations = 0.024 (3) and 0.030 (3) Å in A and B, respectively] and the isoindoline units [maximum deviations 0.009 (3) and 0.008 (3) Å in A and B, respectively] are almostly coplanar, with dihedral angles of 4.25 (9) ad 3.84 (9)° in mol-ecules A and B, respectively. The two independent mol-ecules are connected by π-π inter-actions [centroid-centroid distances 3.5527 (19) and 3.5627 (19) Å]. In the crystal, the A+B pairs are further connected via π-π inter-actions [centroid-centroid distances = 3.693 (2)-3.831 (2) Å], leading to the formation of columns propagating along the a-axis direction. The columns are linked via C-H⋯O inter-actions, leading to the formation of a three-dimensional network.

Related literature

For details concerning the naphthalene group as a fluoro­phore and as a fluorescent chemosensor, see: Li et al. (2010 ▶); Liu et al. (2011 ▶); Iijima et al. (2010 ▶); Hosseini et al. (2010 ▶); Singh et al. (2008 ▶).

Experimental

Crystal data

C19H12N2O3

M = 316.31

Monoclinic,

a = 7.153 (2) Å

b = 15.503 (4) Å

c = 13.446 (4) Å

β = 100.763 (5)°

V = 1464.7 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.20 × 0.20 × 0.10 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.990

8507 measured reflections

5907 independent reflections

4475 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.109

S = 1.02

5907 reflections

433 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 2608 Friedel pairs

Flack parameter: 0.2 (12)

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811045569/su2339sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045569/su2339Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045569/su2339Isup3.cml

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

C19H12N2O3	F(000) = 656
Mr = 316.31	Dx = 1.434 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2910 reflections
a = 7.153 (2) Å	θ = 2.6–26.2°
b = 15.503 (4) Å	µ = 0.10 mm−1
c = 13.446 (4) Å	T = 298 K
β = 100.763 (5)°	Prism, yellow
V = 1464.7 (7) Å3	0.20 × 0.20 × 0.10 mm
Z = 4

Siemens SMART CCD area-detector diffractometer	5907 independent reflections
Radiation source: fine-focus sealed tube	4475 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
Tmin = 0.981, Tmax = 0.990	k = −19→19
8507 measured reflections	l = −12→17

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0506P)2 + 0.109P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
5907 reflections	Δρmax = 0.14 e Å−3
433 parameters	Δρmin = −0.19 e Å−3
1 restraint	Absolute structure: Flack (1983), 2608 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.2 (12)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.1927 (3)	1.08135 (14)	0.28132 (14)	0.0610 (7)
O2	0.0403 (3)	0.73412 (13)	0.26399 (14)	0.0597 (7)
O3	0.1942 (3)	0.94247 (12)	0.05260 (14)	0.0620 (7)
N1	0.1344 (3)	0.92084 (13)	0.24519 (16)	0.0473 (8)
N2	0.1193 (3)	0.85427 (17)	0.17763 (17)	0.0458 (8)
C1	0.1297 (3)	0.98047 (18)	0.40655 (19)	0.0429 (8)
C2	0.1675 (4)	1.0640 (2)	0.3758 (2)	0.0458 (9)
C3	0.1821 (4)	1.1335 (2)	0.4416 (2)	0.0515 (11)
C4	0.1629 (4)	1.12177 (19)	0.5388 (2)	0.0524 (10)
C5	0.1157 (4)	1.0274 (2)	0.6779 (2)	0.0588 (10)
C6	0.0851 (5)	0.9482 (2)	0.7147 (2)	0.0718 (13)
C7	0.0660 (5)	0.8776 (2)	0.6500 (2)	0.0699 (11)
C8	0.0786 (4)	0.88593 (19)	0.5504 (2)	0.0573 (9)
C9	0.1118 (3)	0.96774 (18)	0.50983 (19)	0.0434 (8)
C10	0.1299 (4)	1.0395 (2)	0.5766 (2)	0.0471 (10)
C11	0.1131 (4)	0.9094 (2)	0.33675 (19)	0.0443 (9)
C12	0.0763 (3)	0.76652 (17)	0.1887 (2)	0.0468 (8)
C13	0.1526 (3)	0.87223 (18)	0.07966 (19)	0.0453 (8)
C14	0.1294 (3)	0.78991 (18)	0.0249 (2)	0.0446 (9)
C15	0.0850 (4)	0.7274 (2)	0.0903 (2)	0.0451 (9)
C16	0.0560 (4)	0.6426 (2)	0.0581 (2)	0.0560 (11)
C17	0.0706 (4)	0.6244 (2)	−0.0405 (2)	0.0624 (11)
C18	0.1145 (4)	0.6860 (2)	−0.1048 (2)	0.0606 (11)
C19	0.1445 (4)	0.7711 (2)	−0.0721 (2)	0.0502 (10)
O4	0.5655 (3)	0.70099 (13)	0.22569 (13)	0.0604 (7)
O5	0.5765 (3)	0.84240 (12)	0.45454 (14)	0.0671 (8)
O6	0.6863 (3)	1.05028 (13)	0.23145 (14)	0.0636 (8)
N3	0.6153 (3)	0.86251 (12)	0.25785 (15)	0.0453 (7)
N4	0.6275 (3)	0.93017 (16)	0.32441 (16)	0.0445 (8)
C20	0.6151 (3)	0.80171 (17)	0.09706 (18)	0.0405 (8)
C21	0.5877 (4)	0.7193 (2)	0.13030 (19)	0.0463 (9)
C22	0.5778 (4)	0.6479 (2)	0.0648 (2)	0.0531 (11)
C23	0.5919 (4)	0.65916 (19)	−0.0325 (2)	0.0528 (10)
C24	0.6215 (4)	0.7534 (2)	−0.1750 (2)	0.0622 (11)
C25	0.6385 (5)	0.8332 (2)	−0.2133 (2)	0.0768 (13)
C26	0.6504 (5)	0.9047 (2)	−0.1502 (2)	0.0741 (13)
C27	0.6458 (4)	0.89602 (18)	−0.0499 (2)	0.0586 (10)
C28	0.6263 (3)	0.81455 (19)	−0.00696 (19)	0.0433 (9)
C29	0.6146 (4)	0.7425 (2)	−0.0723 (2)	0.0467 (10)
C30	0.6276 (4)	0.8741 (2)	0.16541 (19)	0.0452 (9)
C31	0.6607 (3)	1.01881 (17)	0.30956 (19)	0.0452 (8)
C32	0.6049 (3)	0.91258 (18)	0.42416 (18)	0.0461 (8)
C33	0.6265 (4)	0.99628 (18)	0.4763 (2)	0.0436 (9)
C34	0.6154 (5)	1.0177 (2)	0.5741 (2)	0.0546 (10)
C35	0.6407 (4)	1.1019 (2)	0.6024 (2)	0.0622 (11)
C36	0.6709 (4)	1.1646 (2)	0.5349 (2)	0.0606 (11)
C37	0.6803 (4)	1.1441 (2)	0.4362 (2)	0.0535 (11)
C38	0.6587 (3)	1.0595 (2)	0.40803 (19)	0.0424 (8)
H1	0.18180	1.03670	0.24790	0.0920*
H3	0.20520	1.18840	0.41890	0.0620*
H4	0.17180	1.16920	0.58180	0.0630*
H5	0.12740	1.07470	0.72120	0.0710*
H6	0.07710	0.94120	0.78240	0.0860*
H7	0.04420	0.82340	0.67520	0.0840*
H8	0.06530	0.83750	0.50880	0.0690*
H11	0.08670	0.85450	0.35830	0.0530*
H16	0.02790	0.59970	0.10130	0.0670*
H17	0.04980	0.56820	−0.06390	0.0750*
H18	0.12440	0.67110	−0.17070	0.0730*
H19	0.17400	0.81370	−0.11540	0.0600*
H4A	0.61750	0.73840	0.26440	0.0910*
H22	0.56140	0.59270	0.08900	0.0640*
H23	0.58680	0.61140	−0.07470	0.0630*
H24	0.61430	0.70550	−0.21720	0.0750*
H25	0.64230	0.84000	−0.28160	0.0920*
H26	0.66160	0.95940	−0.17690	0.0890*
H27	0.65580	0.94480	−0.00910	0.0700*
H30	0.64470	0.92940	0.14200	0.0540*
H34	0.59120	0.97600	0.61970	0.0650*
H35	0.63760	1.11730	0.66890	0.0750*
H36	0.68510	1.22170	0.55600	0.0730*
H37	0.70080	1.18640	0.39030	0.0640*

	U11	U22	U33	U12	U13	U23
O1	0.0772 (13)	0.0557 (13)	0.0489 (11)	−0.0106 (10)	0.0088 (9)	0.0065 (9)
O2	0.0760 (13)	0.0537 (12)	0.0485 (10)	−0.0071 (10)	0.0096 (9)	0.0120 (10)
O3	0.0853 (14)	0.0447 (11)	0.0606 (11)	−0.0025 (9)	0.0257 (10)	0.0050 (9)
N1	0.0519 (13)	0.0472 (14)	0.0428 (12)	−0.0029 (11)	0.0088 (9)	−0.0028 (11)
N2	0.0524 (13)	0.0449 (15)	0.0408 (12)	−0.0026 (10)	0.0109 (10)	0.0001 (10)
C1	0.0357 (13)	0.0446 (15)	0.0467 (15)	0.0003 (11)	0.0031 (10)	0.0005 (12)
C2	0.0401 (15)	0.0473 (17)	0.0482 (15)	−0.0023 (12)	0.0033 (11)	0.0082 (14)
C3	0.0523 (19)	0.0413 (18)	0.0598 (19)	−0.0028 (13)	0.0074 (13)	0.0039 (15)
C4	0.0492 (16)	0.0472 (17)	0.0583 (17)	−0.0015 (13)	0.0035 (12)	−0.0116 (14)
C5	0.0657 (19)	0.0622 (19)	0.0481 (16)	0.0054 (14)	0.0094 (13)	−0.0081 (13)
C6	0.102 (3)	0.070 (2)	0.0469 (16)	0.0097 (18)	0.0233 (15)	0.0064 (16)
C7	0.096 (2)	0.0573 (18)	0.0596 (17)	0.0049 (17)	0.0228 (15)	0.0109 (15)
C8	0.0718 (18)	0.0495 (16)	0.0521 (15)	0.0011 (13)	0.0155 (13)	0.0024 (12)
C9	0.0406 (14)	0.0456 (16)	0.0427 (14)	0.0036 (12)	0.0047 (10)	−0.0021 (13)
C10	0.0386 (15)	0.0509 (19)	0.0505 (16)	0.0036 (12)	0.0052 (12)	−0.0014 (14)
C11	0.0445 (14)	0.0441 (16)	0.0439 (15)	−0.0007 (12)	0.0072 (11)	−0.0003 (12)
C12	0.0407 (14)	0.0442 (15)	0.0534 (15)	−0.0003 (11)	0.0032 (11)	0.0077 (13)
C13	0.0460 (14)	0.0451 (15)	0.0454 (14)	0.0039 (12)	0.0101 (11)	0.0042 (12)
C14	0.0370 (14)	0.0465 (17)	0.0495 (17)	0.0040 (11)	0.0059 (11)	−0.0011 (13)
C15	0.0389 (14)	0.0445 (16)	0.0504 (15)	0.0012 (12)	0.0043 (11)	0.0027 (14)
C16	0.0472 (19)	0.046 (2)	0.073 (2)	−0.0024 (13)	0.0064 (14)	−0.0026 (16)
C17	0.0553 (18)	0.0529 (19)	0.076 (2)	0.0008 (15)	0.0049 (14)	−0.0188 (17)
C18	0.0573 (18)	0.069 (2)	0.0553 (17)	0.0076 (15)	0.0102 (13)	−0.0134 (16)
C19	0.0509 (16)	0.0525 (19)	0.0479 (16)	0.0085 (13)	0.0108 (12)	−0.0002 (13)
O4	0.0766 (14)	0.0559 (13)	0.0485 (11)	−0.0123 (10)	0.0110 (9)	0.0107 (10)
O5	0.1025 (16)	0.0481 (12)	0.0534 (11)	−0.0120 (11)	0.0212 (10)	0.0064 (9)
O6	0.0879 (15)	0.0543 (13)	0.0501 (11)	−0.0116 (11)	0.0167 (10)	0.0097 (10)
N3	0.0517 (12)	0.0437 (13)	0.0398 (11)	−0.0019 (11)	0.0067 (9)	−0.0048 (10)
N4	0.0556 (13)	0.0393 (14)	0.0394 (12)	−0.0034 (10)	0.0112 (10)	−0.0006 (10)
C20	0.0373 (13)	0.0430 (15)	0.0400 (13)	−0.0003 (10)	0.0038 (10)	0.0001 (11)
C21	0.0402 (15)	0.0518 (17)	0.0457 (15)	−0.0046 (12)	0.0051 (11)	0.0013 (15)
C22	0.055 (2)	0.0386 (18)	0.063 (2)	−0.0065 (13)	0.0043 (14)	−0.0001 (15)
C23	0.0503 (16)	0.0472 (18)	0.0584 (17)	−0.0020 (13)	0.0037 (12)	−0.0122 (15)
C24	0.072 (2)	0.067 (2)	0.0480 (16)	0.0105 (15)	0.0123 (13)	−0.0075 (14)
C25	0.110 (3)	0.081 (2)	0.0436 (16)	0.018 (2)	0.0255 (16)	0.0034 (17)
C26	0.113 (3)	0.0608 (19)	0.0530 (17)	0.0070 (18)	0.0271 (16)	0.0134 (15)
C27	0.082 (2)	0.0460 (17)	0.0500 (15)	0.0030 (14)	0.0179 (13)	0.0011 (12)
C28	0.0375 (14)	0.0477 (16)	0.0441 (15)	0.0012 (11)	0.0064 (10)	0.0006 (13)
C29	0.0410 (15)	0.055 (2)	0.0431 (15)	0.0030 (13)	0.0056 (11)	−0.0065 (14)
C30	0.0479 (15)	0.0454 (16)	0.0412 (14)	−0.0008 (12)	0.0054 (11)	0.0017 (12)
C31	0.0448 (15)	0.0439 (15)	0.0465 (14)	−0.0003 (11)	0.0076 (11)	0.0072 (13)
C32	0.0495 (14)	0.0465 (16)	0.0421 (14)	−0.0033 (12)	0.0080 (11)	0.0035 (12)
C33	0.0380 (14)	0.0453 (17)	0.0469 (16)	0.0036 (11)	0.0065 (11)	−0.0024 (12)
C34	0.0529 (17)	0.069 (2)	0.0433 (16)	0.0020 (14)	0.0128 (12)	−0.0029 (14)
C35	0.0544 (17)	0.073 (2)	0.0585 (18)	0.0048 (15)	0.0088 (13)	−0.0235 (17)
C36	0.0568 (18)	0.0501 (19)	0.073 (2)	0.0033 (15)	0.0073 (14)	−0.0154 (17)
C37	0.0496 (19)	0.0461 (19)	0.0627 (19)	−0.0025 (13)	0.0049 (13)	−0.0001 (15)
C38	0.0359 (13)	0.0442 (15)	0.0462 (14)	0.0007 (11)	0.0055 (10)	−0.0022 (13)

O1—C2	1.343 (3)	C6—H6	0.9300
O2—C12	1.200 (3)	C7—H7	0.9300
O3—C13	1.203 (3)	C8—H8	0.9300
O1—H1	0.8200	C11—H11	0.9300
O4—C21	1.352 (3)	C16—H16	0.9300
O5—C32	1.193 (3)	C17—H17	0.9300
O6—C31	1.203 (3)	C18—H18	0.9300
O4—H4A	0.8200	C19—H19	0.9300
N1—C11	1.281 (3)	C20—C21	1.380 (4)
N1—N2	1.366 (3)	C20—C28	1.430 (3)
N2—C12	1.409 (4)	C20—C30	1.443 (4)
N2—C13	1.410 (3)	C21—C22	1.408 (4)
N3—N4	1.371 (3)	C22—C23	1.342 (4)
N3—C30	1.275 (3)	C23—C29	1.419 (4)
N4—C32	1.407 (3)	C24—C29	1.401 (4)
N4—C31	1.415 (4)	C24—C25	1.354 (4)
C1—C2	1.401 (4)	C25—C26	1.389 (4)
C1—C11	1.438 (4)	C26—C27	1.362 (4)
C1—C9	1.432 (4)	C27—C28	1.407 (4)
C2—C3	1.386 (4)	C28—C29	1.414 (4)
C3—C4	1.352 (4)	C31—C38	1.469 (4)
C4—C10	1.409 (4)	C32—C33	1.469 (4)
C5—C6	1.357 (4)	C33—C38	1.391 (4)
C5—C10	1.397 (4)	C33—C34	1.373 (4)
C6—C7	1.389 (4)	C34—C35	1.362 (4)
C7—C8	1.365 (4)	C35—C36	1.374 (4)
C8—C9	1.418 (4)	C36—C37	1.378 (4)
C9—C10	1.420 (4)	C37—C38	1.366 (4)
C12—C15	1.467 (4)	C22—H22	0.9300
C13—C14	1.467 (4)	C23—H23	0.9300
C14—C15	1.385 (4)	C24—H24	0.9300
C14—C19	1.360 (4)	C25—H25	0.9300
C15—C16	1.388 (4)	C26—H26	0.9300
C16—C17	1.378 (4)	C27—H27	0.9300
C17—C18	1.364 (4)	C30—H30	0.9300
C18—C19	1.395 (4)	C34—H34	0.9300
C3—H3	0.9300	C35—H35	0.9300
C4—H4	0.9300	C36—H36	0.9300
C5—H5	0.9300	C37—H37	0.9300
C2—O1—H1	109.00	C16—C17—H17	119.00
C21—O4—H4A	110.00	C19—C18—H18	120.00
N2—N1—C11	121.7 (2)	C17—C18—H18	120.00
N1—N2—C13	117.8 (2)	C14—C19—H19	121.00
C12—N2—C13	111.6 (2)	C18—C19—H19	121.00
N1—N2—C12	130.6 (2)	C21—C20—C28	118.9 (2)
N4—N3—C30	121.4 (2)	C28—C20—C30	120.5 (2)
C31—N4—C32	112.0 (2)	C21—C20—C30	120.6 (2)
N3—N4—C32	118.0 (2)	O4—C21—C20	123.4 (2)
N3—N4—C31	130.0 (2)	C20—C21—C22	121.3 (2)
C9—C1—C11	121.1 (2)	O4—C21—C22	115.3 (3)
C2—C1—C11	120.8 (2)	C21—C22—C23	120.2 (3)
C2—C1—C9	118.1 (2)	C22—C23—C29	121.4 (3)
C1—C2—C3	121.7 (2)	C25—C24—C29	120.5 (3)
O1—C2—C3	116.2 (3)	C24—C25—C26	119.8 (3)
O1—C2—C1	122.1 (3)	C25—C26—C27	121.1 (3)
C2—C3—C4	120.2 (3)	C26—C27—C28	121.2 (3)
C3—C4—C10	121.6 (3)	C20—C28—C27	123.7 (3)
C6—C5—C10	121.5 (3)	C27—C28—C29	117.0 (2)
C5—C6—C7	119.2 (3)	C20—C28—C29	119.4 (3)
C6—C7—C8	121.5 (3)	C23—C29—C24	120.6 (3)
C7—C8—C9	120.6 (3)	C23—C29—C28	118.9 (2)
C1—C9—C10	119.4 (2)	C24—C29—C28	120.6 (3)
C8—C9—C10	117.4 (2)	N3—C30—C20	120.3 (3)
C1—C9—C8	123.2 (2)	O6—C31—N4	125.0 (2)
C5—C10—C9	119.8 (3)	N4—C31—C38	105.1 (2)
C4—C10—C9	118.9 (2)	O6—C31—C38	129.9 (3)
C4—C10—C5	121.4 (3)	O5—C32—C33	130.7 (2)
N1—C11—C1	120.7 (3)	N4—C32—C33	105.3 (2)
N2—C12—C15	104.9 (2)	O5—C32—N4	124.1 (2)
O2—C12—C15	129.8 (3)	C32—C33—C38	108.8 (2)
O2—C12—N2	125.4 (2)	C34—C33—C38	120.5 (3)
N2—C13—C14	105.9 (2)	C32—C33—C34	130.6 (3)
O3—C13—N2	123.8 (2)	C33—C34—C35	118.1 (3)
O3—C13—C14	130.3 (2)	C34—C35—C36	121.5 (3)
C13—C14—C15	107.9 (2)	C35—C36—C37	121.0 (3)
C13—C14—C19	130.2 (3)	C36—C37—C38	117.7 (3)
C15—C14—C19	121.8 (3)	C31—C38—C37	130.0 (3)
C14—C15—C16	120.2 (2)	C33—C38—C37	121.2 (2)
C12—C15—C16	130.1 (3)	C31—C38—C33	108.8 (3)
C12—C15—C14	109.7 (3)	C21—C22—H22	120.00
C15—C16—C17	117.4 (3)	C23—C22—H22	120.00
C16—C17—C18	122.3 (3)	C22—C23—H23	119.00
C17—C18—C19	120.2 (3)	C29—C23—H23	119.00
C14—C19—C18	118.0 (3)	C25—C24—H24	120.00
C4—C3—H3	120.00	C29—C24—H24	120.00
C2—C3—H3	120.00	C24—C25—H25	120.00
C10—C4—H4	119.00	C26—C25—H25	120.00
C3—C4—H4	119.00	C25—C26—H26	119.00
C10—C5—H5	119.00	C27—C26—H26	119.00
C6—C5—H5	119.00	C26—C27—H27	119.00
C5—C6—H6	120.00	C28—C27—H27	119.00
C7—C6—H6	120.00	N3—C30—H30	120.00
C8—C7—H7	119.00	C20—C30—H30	120.00
C6—C7—H7	119.00	C33—C34—H34	121.00
C9—C8—H8	120.00	C35—C34—H34	121.00
C7—C8—H8	120.00	C34—C35—H35	119.00
N1—C11—H11	120.00	C36—C35—H35	119.00
C1—C11—H11	120.00	C35—C36—H36	120.00
C15—C16—H16	121.00	C37—C36—H36	119.00
C17—C16—H16	121.00	C36—C37—H37	121.00
C18—C17—H17	119.00	C38—C37—H37	121.00
C11—N1—N2—C12	1.8 (4)	C13—C14—C15—C16	−179.7 (2)
C11—N1—N2—C13	−177.5 (2)	C13—C14—C15—C12	0.4 (3)
N2—N1—C11—C1	180.0 (2)	C13—C14—C19—C18	−179.9 (2)
C13—N2—C12—C15	0.4 (3)	C19—C14—C15—C12	−179.3 (2)
C12—N2—C13—O3	−179.0 (2)	C19—C14—C15—C16	0.6 (4)
N1—N2—C13—C14	179.3 (2)	C15—C14—C19—C18	−0.2 (4)
C12—N2—C13—C14	−0.1 (3)	C14—C15—C16—C17	−0.9 (4)
N1—N2—C13—O3	0.4 (4)	C12—C15—C16—C17	178.9 (3)
N1—N2—C12—O2	1.5 (4)	C15—C16—C17—C18	1.0 (4)
C13—N2—C12—O2	−179.3 (2)	C16—C17—C18—C19	−0.7 (5)
N1—N2—C12—C15	−178.9 (2)	C17—C18—C19—C14	0.3 (4)
C30—N3—N4—C31	−2.6 (4)	C30—C20—C21—C22	−179.1 (3)
C30—N3—N4—C32	177.5 (2)	C28—C20—C21—C22	2.4 (4)
N4—N3—C30—C20	179.7 (2)	C30—C20—C21—O4	2.0 (4)
C32—N4—C31—C38	0.0 (3)	C28—C20—C30—N3	179.2 (2)
C31—N4—C32—O5	−179.6 (2)	C30—C20—C28—C29	179.7 (2)
N3—N4—C32—C33	179.6 (2)	C21—C20—C30—N3	0.7 (4)
C31—N4—C32—C33	−0.3 (3)	C28—C20—C21—O4	−176.5 (2)
N3—N4—C32—O5	0.3 (4)	C30—C20—C28—C27	−1.3 (4)
N3—N4—C31—O6	−0.6 (4)	C21—C20—C28—C27	177.2 (2)
C32—N4—C31—O6	179.3 (2)	C21—C20—C28—C29	−1.8 (3)
N3—N4—C31—C38	−179.9 (2)	O4—C21—C22—C23	177.9 (3)
C9—C1—C2—O1	177.8 (2)	C20—C21—C22—C23	−1.1 (4)
C9—C1—C11—N1	−178.1 (2)	C21—C22—C23—C29	−0.8 (4)
C11—C1—C2—C3	179.3 (3)	C22—C23—C29—C28	1.3 (4)
C11—C1—C2—O1	−1.1 (4)	C22—C23—C29—C24	−177.5 (3)
C9—C1—C2—C3	−1.9 (4)	C25—C24—C29—C28	−0.3 (4)
C2—C1—C9—C8	−178.3 (2)	C29—C24—C25—C26	0.4 (5)
C2—C1—C9—C10	0.9 (3)	C25—C24—C29—C23	178.4 (3)
C2—C1—C11—N1	0.7 (4)	C24—C25—C26—C27	0.2 (5)
C11—C1—C9—C10	179.7 (2)	C25—C26—C27—C28	−0.9 (5)
C11—C1—C9—C8	0.5 (4)	C26—C27—C28—C29	0.9 (4)
C1—C2—C3—C4	1.1 (4)	C26—C27—C28—C20	−178.1 (3)
O1—C2—C3—C4	−178.6 (3)	C27—C28—C29—C24	−0.3 (4)
C2—C3—C4—C10	0.7 (4)	C20—C28—C29—C24	178.8 (2)
C3—C4—C10—C9	−1.6 (4)	C27—C28—C29—C23	−179.1 (3)
C3—C4—C10—C5	178.1 (3)	C20—C28—C29—C23	0.0 (4)
C6—C5—C10—C9	0.1 (4)	O6—C31—C38—C37	2.0 (4)
C10—C5—C6—C7	−0.5 (5)	N4—C31—C38—C33	0.3 (3)
C6—C5—C10—C4	−179.6 (3)	N4—C31—C38—C37	−178.8 (3)
C5—C6—C7—C8	0.5 (5)	O6—C31—C38—C33	−178.9 (3)
C6—C7—C8—C9	0.0 (5)	O5—C32—C33—C34	−1.8 (5)
C7—C8—C9—C10	−0.4 (4)	O5—C32—C33—C38	179.7 (3)
C7—C8—C9—C1	178.9 (3)	N4—C32—C33—C34	178.9 (3)
C8—C9—C10—C4	−180.0 (3)	N4—C32—C33—C38	0.5 (3)
C1—C9—C10—C5	−179.0 (2)	C32—C33—C34—C35	−179.6 (3)
C1—C9—C10—C4	0.7 (4)	C38—C33—C34—C35	−1.3 (5)
C8—C9—C10—C5	0.3 (4)	C32—C33—C38—C31	−0.5 (3)
N2—C12—C15—C16	179.7 (3)	C32—C33—C38—C37	178.7 (2)
N2—C12—C15—C14	−0.5 (3)	C34—C33—C38—C31	−179.1 (3)
O2—C12—C15—C14	179.1 (3)	C34—C33—C38—C37	0.1 (4)
O2—C12—C15—C16	−0.7 (5)	C33—C34—C35—C36	1.9 (5)
N2—C13—C14—C19	179.5 (3)	C34—C35—C36—C37	−1.3 (5)
O3—C13—C14—C15	178.6 (3)	C35—C36—C37—C38	0.0 (4)
N2—C13—C14—C15	−0.2 (3)	C36—C37—C38—C31	179.6 (2)
O3—C13—C14—C19	−1.7 (5)	C36—C37—C38—C33	0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.83	2.555 (3)	147
O4—H4A···N3	0.82	1.93	2.555 (3)	133
C18—H18···O6i	0.93	2.53	3.204 (4)	129
C35—H35···O4ii	0.93	2.56	3.339 (4)	141

π–π	Distance
Cg2···Cg4	3.5627 (19)
Cg4···Cg6	3.5527 (19)
Cg1···Cg6i	3.7758 (19)
Cg2···Cg5i	3.7759 (19)
Cg2···Cg8i	3.693 (2)
Cg3···Cg8i	3.784 (2)
Cg4···Cg6i	3.7065 (19)
Cg4···Cg7i	3.831 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.83	2.555 (3)	147
O4—H4A⋯N3	0.82	1.93	2.555 (3)	133
C18—H18⋯O6i	0.93	2.53	3.204 (4)	129
C35—H35⋯O4ii	0.93	2.56	3.339 (4)	141

Symmetry codes: (i) ; (ii) .