Charge-transfer complexes of N-methyl-, N-iso­propyl-, N-butyl- and N-iso­butyl­carbazole with 3,5-di­nitro­benzoic acid

In the title four compounds, C₁₃H₁₁N·C₇H₄N₂O₆, (I), C₁₅H₁₅N·C₇H₄N₂O₆, (II), C₁₆H₁₇N·C₇H₄N₂O₆, (III), and C₁₆H₁₇N·C₇H₄N₂O₆, (IV), the donor and acceptor mol­ecules are stacked alternately to form one-dimensional columns. In (I), the N-methyl group of the donor is nearly eclipsed with respect to one of the nitro groups of the neighboring acceptor in a column, whereas the N-iso­propyl, N-butyl and N-iso­butyl groups are in anti positions with respect to one of the nitro groups of the neighboring acceptor in compounds (II)-(IV).

S1. Comment

Crystals of (I) underwent photoredox reactions initiated by the excited nitro group, leading to α-oxidation of the N-alkyl groups. Complexes (III) and (IV) were less photoreactive than (I), and no reaction was observed for (II) (Ito et al., 1998).

In (I), the N-methyl group of the donor is nearly eclipsed to one of the nitro groups of the neighboring acceptor in a column, whereas the N-isopropyl, N-butyl and N-isobutyl groups are in anti positions with respect to one of the nitro groups of the neighboring acceptor in (II)-(IV).

S2. Experimental

Equimolar mixtures of N-alkylcarbazoles and 3,5-dinitrobenzoic acid were recrystallized from ethylacetate [for (I)], acetonitrile [for (II)–(III)] and acetone [for (IV)].

S3. Refinement

In compounds (I)–(IV), the 3,5-dinitrobenzoic acid molecules form a dimeric structure with cyclic hydrogen bonds. The acid proton has two possible positions with site-occupation factors of 50%. They were located from difference syntheses and refined isotropically. The O—H bond lengths are 0.73 (5)–0.88 (5) Å for (I), 0.78 (4)–0.82 (4) Å for (II), 0.64 (7)–1.01 (8) Å for (III) and 0.80 (6)–0.90 (8) Å for (IV). The other H-atom positional parameters were calculated geometrically and fixed with U_iso(H) = 1.2U_eq(parent atom).

Computing details

For all compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN.

(I)

Crystal data

C13H11N·C7H4N2O6	Z = 2
Mr = 393.36	Dx = 1.446 Mg m^−3
Triclinic, P1	Mo Kα radiation, λ = 0.71073 Å
a = 8.414 (1) Å	Cell parameters from 25 reflections
b = 15.763 (2) Å	θ = 14.8–15.0°
c = 6.991 (1) Å	µ = 0.11 mm^−1
α = 91.82 (1)°	T = 298 K
β = 99.91 (1)°	Plate-like, orange
γ = 81.59 (1)°	0.6 × 0.4 × 0.1 mm
V = 903.6 (2) Å^3

Data collection

Rigaku AFC-7R diffractometer	θmax = 27.5°, θmin = 2.5°
θ–2θ scans	h = −6→11
5045 measured reflections	k = −20→20
4128 independent reflections	l = −9→9
2977 reflections with I > 2σ(I)	3 standard reflections every 150 reflections
Rint = 0.005	intensity decay: none

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0715P)^2 + 0.1508P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.147	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.29 e Å^−3
4128 reflections	Δρmin = −0.18 e Å^−3
270 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.3140 (2)	0.54272 (9)	0.3736 (2)	0.0704 (4)
O2	0.5349 (2)	0.60566 (9)	0.4766 (2)	0.0710 (4)
O3	0.5136 (2)	0.90733 (9)	0.3326 (3)	0.0834 (4)
O4	0.2827 (2)	0.98623 (8)	0.2436 (2)	0.0822 (4)
O5	−0.2015 (2)	0.8524 (1)	0.0584 (3)	0.0887 (5)
O6	−0.1918 (2)	0.7173 (1)	0.1029 (3)	0.0908 (5)
N7	0.3667 (2)	0.91724 (9)	0.2839 (2)	0.0596 (4)
N8	−0.1284 (2)	0.7826 (1)	0.1113 (2)	0.0635 (4)
N9	−0.0120 (2)	0.7610 (1)	−0.3163 (2)	0.0611 (4)
C10	0.3879 (2)	0.6073 (1)	0.3959 (2)	0.0541 (4)
C11	0.2954 (2)	0.6914 (1)	0.3249 (2)	0.0490 (3)
C12	0.3735 (2)	0.7634 (1)	0.3352 (2)	0.0493 (3)
C13	0.2834 (2)	0.8407 (1)	0.2723 (2)	0.0487 (3)
C14	0.1193 (2)	0.8496 (1)	0.1991 (2)	0.0507 (4)
C15	0.0465 (2)	0.7761 (1)	0.1896 (2)	0.0498 (4)
C16	0.1307 (2)	0.6974 (1)	0.2502 (2)	0.0506 (4)
C17	0.1087 (2)	0.8131 (1)	−0.2849 (2)	0.0524 (4)
C18	0.0977 (2)	0.9014 (1)	−0.3100 (3)	0.0688 (5)
C19	0.2411 (3)	0.9368 (1)	−0.2651 (3)	0.0806 (6)
C20	0.3892 (3)	0.8878 (2)	−0.1986 (3)	0.0795 (6)
C21	0.3991 (2)	0.8016 (1)	−0.1730 (3)	0.0665 (5)
C22	0.2587 (2)	0.7628 (1)	−0.2161 (2)	0.0512 (4)
C23	0.2270 (2)	0.6762 (1)	−0.2055 (2)	0.0559 (4)
C24	0.3221 (3)	0.5983 (2)	−0.1466 (3)	0.0809 (6)
C25	0.2462 (5)	0.5255 (2)	−0.1544 (4)	0.1098 (10)
C26	0.0810 (5)	0.5293 (2)	−0.2188 (5)	0.117 (1)
C27	−0.0156 (3)	0.6041 (2)	−0.2773 (4)	0.0922 (7)
C28	0.0583 (2)	0.6780 (1)	−0.2692 (3)	0.0615 (4)
C29	−0.1823 (2)	0.7891 (2)	−0.3917 (3)	0.0859 (7)
H1	0.351 (6)	0.503 (3)	0.424 (6)	0.0696 (2)*	0.50
H2	0.585 (6)	0.557 (4)	0.528 (7)	0.0809 (2)*	0.50
H12	0.4884	0.7593	0.3855	0.0561*
H14	0.0576	0.9047	0.1564	0.0574*
H16	0.0760	0.6478	0.2416	0.0572*
H18	−0.0056	0.9369	−0.3543	0.0788*
H19	0.2351	0.9987	−0.2832	0.0934*
H20	0.4882	0.9151	−0.1656	0.0920*
H21	0.5029	0.7665	−0.1286	0.0738*
H24	0.4370	0.5938	−0.1008	0.0910*
H25	0.3043	0.4699	−0.1197	0.1273*
H26	0.0335	0.4763	−0.2168	0.1279*
H27	−0.1311	0.6052	−0.3223	0.1088*
H29A	−0.2417	0.7402	−0.4013	0.0986*
H29B	−0.1942	0.8131	−0.5184	0.0986*
H29C	−0.2280	0.8309	−0.3061	0.0986*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0756 (9)	0.0456 (7)	0.0824 (9)	−0.0108 (6)	−0.0118 (7)	0.0115 (6)
O2	0.0556 (7)	0.0527 (7)	0.097 (1)	−0.0010 (6)	−0.0056 (7)	0.0145 (7)
O3	0.0602 (8)	0.0673 (9)	0.122 (1)	−0.0201 (7)	0.0028 (8)	0.0144 (8)
O4	0.0793 (9)	0.0466 (7)	0.119 (1)	−0.0067 (6)	0.0124 (8)	0.0136 (7)
O5	0.0586 (8)	0.0788 (10)	0.114 (1)	0.0117 (7)	−0.0080 (8)	0.0024 (9)
O6	0.0591 (8)	0.084 (1)	0.124 (1)	−0.0210 (8)	−0.0084 (8)	0.0036 (9)
N7	0.0620 (9)	0.0497 (8)	0.0684 (9)	−0.0112 (7)	0.0106 (7)	0.0065 (6)
N8	0.0502 (8)	0.0675 (10)	0.0681 (9)	−0.0030 (7)	0.0021 (7)	−0.0017 (7)
N9	0.0372 (7)	0.079 (1)	0.0664 (9)	−0.0127 (7)	0.0037 (6)	−0.0023 (7)
C10	0.0550 (9)	0.0467 (8)	0.0570 (9)	−0.0054 (7)	0.0000 (7)	0.0038 (7)
C11	0.0521 (8)	0.0456 (8)	0.0463 (8)	−0.0033 (6)	0.0027 (6)	0.0029 (6)
C12	0.0472 (8)	0.0490 (8)	0.0499 (8)	−0.0060 (6)	0.0034 (6)	0.0036 (6)
C13	0.0530 (8)	0.0454 (8)	0.0481 (8)	−0.0075 (6)	0.0083 (6)	0.0034 (6)
C14	0.0530 (9)	0.0475 (8)	0.0487 (8)	0.0012 (7)	0.0074 (6)	0.0035 (6)
C15	0.0446 (8)	0.0539 (9)	0.0481 (8)	−0.0034 (7)	0.0033 (6)	0.0000 (6)
C16	0.0532 (8)	0.0467 (8)	0.0508 (8)	−0.0093 (7)	0.0038 (7)	−0.0003 (6)
C17	0.0446 (8)	0.0635 (10)	0.0501 (8)	−0.0086 (7)	0.0107 (6)	−0.0046 (7)
C18	0.072 (1)	0.065 (1)	0.069 (1)	0.0006 (9)	0.0174 (9)	−0.0016 (9)
C19	0.105 (2)	0.067 (1)	0.083 (1)	−0.035 (1)	0.034 (1)	−0.015 (1)
C20	0.075 (1)	0.097 (2)	0.078 (1)	−0.043 (1)	0.021 (1)	−0.020 (1)
C21	0.0454 (9)	0.096 (1)	0.061 (1)	−0.0208 (9)	0.0100 (7)	−0.0121 (10)
C22	0.0409 (8)	0.068 (1)	0.0453 (8)	−0.0097 (7)	0.0085 (6)	−0.0052 (7)
C23	0.0551 (9)	0.064 (1)	0.0483 (8)	−0.0067 (8)	0.0105 (7)	−0.0004 (7)
C24	0.090 (1)	0.082 (1)	0.064 (1)	0.010 (1)	0.013 (1)	0.008 (1)
C25	0.170 (3)	0.064 (1)	0.096 (2)	0.002 (2)	0.036 (2)	0.016 (1)
C26	0.165 (3)	0.080 (2)	0.121 (2)	−0.050 (2)	0.038 (2)	−0.001 (2)
C27	0.102 (2)	0.094 (2)	0.094 (2)	−0.052 (2)	0.024 (1)	−0.010 (1)
C28	0.062 (1)	0.072 (1)	0.0558 (9)	−0.0236 (9)	0.0142 (8)	−0.0049 (8)
C29	0.0434 (9)	0.133 (2)	0.077 (1)	−0.011 (1)	0.0001 (9)	−0.004 (1)

Geometric parameters (Å, º)

O1—C10	1.260 (2)	C17—C22	1.406 (2)
O1—H1	0.73 (5)	C18—C19	1.385 (3)
O2—C10	1.265 (2)	C18—H18	0.970
O2—H2	0.88 (5)	C19—C20	1.382 (3)
O3—N7	1.213 (2)	C19—H19	0.980
O4—N7	1.220 (2)	C20—C21	1.363 (3)
O5—N8	1.214 (2)	C20—H20	0.982
O6—N8	1.222 (2)	C21—C22	1.393 (3)
N7—C13	1.474 (2)	C21—H21	0.970
N8—C15	1.469 (2)	C22—C23	1.435 (3)
N9—C17	1.382 (2)	C23—C24	1.395 (3)
N9—C28	1.379 (2)	C23—C28	1.409 (2)
N9—C29	1.449 (2)	C24—C25	1.388 (4)
C10—C11	1.489 (2)	C24—H24	0.958
C11—C12	1.386 (2)	C25—C26	1.379 (6)
C11—C16	1.385 (2)	C25—H25	0.957
C12—C13	1.379 (2)	C26—C27	1.362 (4)
C12—H12	0.964	C26—H26	0.979
C13—C14	1.376 (2)	C27—C28	1.394 (4)
C14—C15	1.381 (2)	C27—H27	0.966
C14—H14	0.973	C29—H29A	0.972
C15—C16	1.376 (2)	C29—H29B	0.958
C16—H16	0.960	C29—H29C	0.959
C17—C18	1.397 (3)
C10—O1—H1	120 (4)	C19—C18—H18	121.2
C10—O2—H2	116 (3)	C18—C19—C20	122.2 (2)
O3—N7—O4	124.5 (2)	C18—C19—H19	117.8
O3—N7—C13	117.9 (1)	C20—C19—H19	120.1
O4—N7—C13	117.6 (1)	C19—C20—C21	120.6 (2)
O5—N8—O6	123.8 (2)	C19—C20—H20	120.1
O5—N8—C15	118.2 (2)	C21—C20—H20	119.3
O6—N8—C15	118.0 (1)	C20—C21—C22	119.6 (2)
C17—N9—C28	108.5 (1)	C20—C21—H21	121.2
C17—N9—C29	125.3 (2)	C22—C21—H21	119.2
C28—N9—C29	126.2 (2)	C17—C22—C21	119.4 (2)
O1—C10—O2	124.4 (1)	C17—C22—C23	107.0 (1)
O1—C10—C11	117.8 (1)	C21—C22—C23	133.6 (1)
O2—C10—C11	117.7 (2)	C22—C23—C24	134.7 (2)
C10—C11—C12	120.2 (1)	C22—C23—C28	106.3 (1)
C10—C11—C16	119.6 (2)	C24—C23—C28	119.0 (2)
C12—C11—C16	120.2 (1)	C23—C24—C25	118.4 (2)
C11—C12—C13	118.7 (1)	C23—C24—H24	122.2
C11—C12—H12	120.4	C25—C24—H24	119.4
C13—C12—H12	120.9	C24—C25—C26	121.3 (2)
N7—C13—C12	118.6 (1)	C24—C25—H25	122.8
N7—C13—C14	118.6 (1)	C26—C25—H25	115.9
C12—C13—C14	122.9 (2)	C25—C26—C27	122.0 (3)
C13—C14—C15	116.6 (1)	C25—C26—H26	117.6
C13—C14—H14	121.7	C27—C26—H26	120.4
C15—C14—H14	121.7	C26—C27—C28	117.6 (3)
N8—C15—C14	118.4 (1)	C26—C27—H27	120.5
N8—C15—C16	118.8 (1)	C28—C27—H27	121.8
C14—C15—C16	122.9 (1)	N9—C28—C23	109.3 (2)
C11—C16—C15	118.8 (2)	N9—C28—C27	128.9 (2)
C11—C16—H16	120.6	C23—C28—C27	121.8 (2)
C15—C16—H16	120.6	N9—C29—H29A	109.3
N9—C17—C18	129.8 (1)	N9—C29—H29B	110.4
N9—C17—C22	109.0 (1)	N9—C29—H29C	110.2
C18—C17—C22	121.2 (2)	H29A—C29—H29B	108.6
C17—C18—C19	117.0 (2)	H29A—C29—H29C	108.5
C17—C18—H18	121.8	H29B—C29—H29C	109.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.73 (5)	1.92 (5)	2.648 (2)	172 (5)
O2—H2···O1^i	0.88 (5)	1.77 (5)	2.648 (2)	179 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

(II)

Crystal data

C15H15N·C7H4N2O6	Dx = 1.368 Mg m^−3
Mr = 421.41	Mo Kα radiation, λ = 0.71073 Å
Monoclinic, P21/a	Cell parameters from 25 reflections
a = 8.504 (2) Å	θ = 12.9–14.9°
b = 29.533 (4) Å	µ = 0.10 mm^−1
c = 8.568 (2) Å	T = 298 K
β = 108.05 (2)°	Prism, orange
V = 2045.8 (7) Å^3	0.5 × 0.5 × 0.5 mm
Z = 4

Data collection

Rigaku AFC-7R diffractometer	θmax = 27.5°, θmin = 2.5°
ω scans	h = 0→11
4990 measured reflections	k = 0→38
4685 independent reflections	l = −11→11
3283 reflections with I > 2σ(I)	3 standard reflections every 150 reflections
Rint = 0.011	intensity decay: none

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.041	w = 1/[σ^2(Fo^2) + (0.0542P)^2 + 0.4038P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.122	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.21 e Å^−3
4685 reflections	Δρmin = −0.16 e Å^−3
288 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.0226 (2)	0.04384 (4)	0.8774 (2)	0.0606 (3)
O2	−0.1986 (2)	0.00141 (4)	0.8629 (2)	0.0596 (3)
O3	−0.7332 (2)	0.04803 (7)	0.4968 (2)	0.0970 (5)
O4	−0.7483 (2)	0.10037 (6)	0.3189 (2)	0.1084 (6)
O5	−0.2710 (2)	0.19129 (5)	0.3509 (2)	0.0817 (4)
O6	−0.0299 (2)	0.16733 (5)	0.4925 (2)	0.0758 (4)
N7	−0.6713 (2)	0.07701 (6)	0.4337 (2)	0.0707 (4)
N8	−0.1798 (2)	0.16475 (5)	0.4448 (2)	0.0564 (4)
N9	−0.1902 (2)	0.15813 (4)	0.9916 (2)	0.0465 (3)
C10	−0.1272 (2)	0.03405 (5)	0.8168 (2)	0.0444 (3)
C11	−0.2308 (2)	0.06314 (5)	0.6819 (2)	0.0424 (3)
C12	−0.3995 (2)	0.05581 (5)	0.6200 (2)	0.0472 (3)
C13	−0.4926 (2)	0.08431 (6)	0.4990 (2)	0.0500 (4)
C14	−0.4246 (2)	0.12029 (5)	0.4386 (2)	0.0507 (4)
C15	−0.2578 (2)	0.12641 (5)	0.5040 (2)	0.0454 (3)
C16	−0.1577 (2)	0.09853 (5)	0.6235 (2)	0.0443 (3)
C17	−0.3188 (2)	0.17607 (5)	0.8648 (2)	0.0471 (4)
C18	−0.3213 (2)	0.21217 (6)	0.7593 (2)	0.0596 (4)
C19	−0.4665 (3)	0.22179 (6)	0.6387 (3)	0.0715 (6)
C20	−0.6101 (3)	0.19693 (8)	0.6203 (3)	0.0731 (6)
C21	−0.6102 (2)	0.16132 (7)	0.7240 (2)	0.0625 (5)
C22	−0.4635 (2)	0.15013 (6)	0.8467 (2)	0.0483 (4)
C23	−0.4179 (2)	0.11450 (5)	0.9659 (2)	0.0468 (4)
C24	−0.5036 (2)	0.07788 (6)	1.0045 (2)	0.0602 (4)
C25	−0.4202 (3)	0.04785 (6)	1.1229 (3)	0.0676 (5)
C26	−0.2531 (3)	0.05316 (6)	1.2039 (2)	0.0633 (5)
C27	−0.1636 (2)	0.08915 (6)	1.1707 (2)	0.0527 (4)
C28	−0.2487 (2)	0.11996 (5)	1.0511 (2)	0.0434 (3)
C29	−0.0238 (2)	0.17727 (6)	1.0673 (2)	0.0524 (4)
C30	0.0890 (2)	0.16815 (6)	0.9637 (2)	0.0677 (5)
C31	−0.0289 (2)	0.22717 (7)	1.1096 (2)	0.0735 (6)
H1	0.080 (5)	0.031 (1)	0.952 (6)	0.0560 (1)*	0.50
H2	−0.144 (5)	−0.013 (1)	0.943 (5)	0.0530 (1)*	0.50
H12	−0.4503	0.0307	0.6580	0.0528*
H14	−0.4920	0.1396	0.3528	0.0566*
H16	−0.0384	0.1035	0.6665	0.0491*
H18	−0.2218	0.2296	0.7704	0.0669*
H19	−0.4721	0.2463	0.5627	0.0785*
H20	−0.7118	0.2047	0.5348	0.0838*
H21	−0.7106	0.1444	0.7119	0.0694*
H24	−0.6204	0.0741	0.9492	0.0671*
H25	−0.4772	0.0219	1.1493	0.0762*
H26	−0.1980	0.0316	1.2862	0.0685*
H27	−0.0468	0.0922	1.2269	0.0583*
H29	0.0242	0.1619	1.1712	0.0560*
H30A	0.1966	0.1807	1.0164	0.0764*
H30B	0.0426	0.1818	0.8580	0.0764*
H30C	0.0984	0.1360	0.9512	0.0764*
H31A	−0.0823	0.2441	1.0094	0.0825*
H31B	0.0793	0.2390	1.1585	0.0825*
H31C	−0.0939	0.2315	1.1832	0.0825*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0483 (7)	0.0612 (8)	0.0639 (8)	0.0032 (6)	0.0051 (6)	0.0221 (6)
O2	0.0602 (7)	0.0528 (7)	0.0599 (7)	−0.0017 (6)	0.0102 (6)	0.0206 (6)
O3	0.0576 (9)	0.116 (1)	0.109 (1)	−0.0145 (9)	0.0134 (9)	0.019 (1)
O4	0.0598 (9)	0.111 (1)	0.124 (1)	0.0116 (9)	−0.0173 (9)	0.036 (1)
O5	0.108 (1)	0.0617 (8)	0.0807 (9)	0.0196 (8)	0.0365 (9)	0.0353 (7)
O6	0.0753 (10)	0.0687 (9)	0.0779 (9)	−0.0199 (7)	0.0160 (8)	0.0140 (7)
N7	0.0499 (9)	0.074 (1)	0.077 (1)	0.0049 (8)	0.0033 (8)	0.0019 (9)
N8	0.083 (1)	0.0422 (7)	0.0457 (7)	0.0028 (7)	0.0228 (7)	0.0050 (6)
N9	0.0425 (7)	0.0443 (7)	0.0542 (7)	−0.0099 (5)	0.0173 (6)	−0.0018 (6)
C10	0.0481 (9)	0.0409 (8)	0.0435 (8)	0.0037 (6)	0.0130 (7)	0.0051 (6)
C11	0.0490 (8)	0.0377 (7)	0.0395 (7)	0.0050 (6)	0.0124 (6)	0.0014 (6)
C12	0.0507 (9)	0.0432 (8)	0.0473 (8)	0.0015 (7)	0.0148 (7)	0.0017 (7)
C13	0.0461 (8)	0.0515 (9)	0.0477 (8)	0.0077 (7)	0.0077 (7)	−0.0025 (7)
C14	0.062 (1)	0.0451 (8)	0.0415 (8)	0.0136 (7)	0.0102 (7)	0.0045 (6)
C15	0.0613 (10)	0.0371 (7)	0.0383 (7)	0.0028 (7)	0.0162 (7)	0.0012 (6)
C16	0.0510 (9)	0.0396 (8)	0.0407 (7)	0.0025 (6)	0.0120 (6)	0.0010 (6)
C17	0.0491 (9)	0.0420 (8)	0.0548 (9)	0.0002 (7)	0.0225 (7)	−0.0059 (7)
C18	0.071 (1)	0.0459 (9)	0.067 (1)	0.0034 (8)	0.0292 (10)	0.0017 (8)
C19	0.091 (2)	0.056 (1)	0.071 (1)	0.026 (1)	0.029 (1)	0.0080 (9)
C20	0.068 (1)	0.076 (1)	0.071 (1)	0.031 (1)	0.014 (1)	−0.004 (1)
C21	0.0446 (9)	0.073 (1)	0.070 (1)	0.0091 (8)	0.0181 (8)	−0.0151 (10)
C22	0.0427 (8)	0.0509 (9)	0.0560 (9)	0.0007 (7)	0.0221 (7)	−0.0100 (7)
C23	0.0459 (8)	0.0475 (8)	0.0529 (9)	−0.0094 (7)	0.0239 (7)	−0.0124 (7)
C24	0.061 (1)	0.062 (1)	0.067 (1)	−0.0234 (9)	0.0325 (9)	−0.0154 (9)
C25	0.095 (1)	0.052 (1)	0.070 (1)	−0.029 (1)	0.045 (1)	−0.0120 (9)
C26	0.098 (2)	0.0448 (9)	0.0548 (10)	−0.0073 (9)	0.035 (1)	−0.0014 (8)
C27	0.060 (1)	0.0501 (9)	0.0500 (9)	−0.0030 (8)	0.0206 (8)	−0.0049 (7)
C28	0.0477 (8)	0.0407 (7)	0.0467 (8)	−0.0084 (6)	0.0220 (7)	−0.0080 (6)
C29	0.0473 (9)	0.0563 (9)	0.0529 (9)	−0.0168 (7)	0.0148 (7)	−0.0054 (7)
C30	0.052 (1)	0.075 (1)	0.082 (1)	−0.0136 (9)	0.0291 (9)	−0.013 (1)
C31	0.078 (1)	0.062 (1)	0.086 (1)	−0.027 (1)	0.034 (1)	−0.025 (1)

Geometric parameters (Å, º)

O1—C10	1.251 (2)	C19—C20	1.391 (3)
O1—H1	0.78 (4)	C19—H19	0.966
O2—C10	1.266 (2)	C20—C21	1.377 (3)
O2—H2	0.82 (4)	C20—H20	0.972
O3—N7	1.216 (3)	C21—C22	1.399 (2)
O4—N7	1.214 (2)	C21—H21	0.967
O5—N8	1.215 (2)	C22—C23	1.433 (2)
O6—N8	1.215 (2)	C23—C24	1.400 (3)
N7—C13	1.463 (2)	C23—C28	1.407 (2)
N8—C15	1.479 (2)	C24—C25	1.368 (3)
N9—C17	1.387 (2)	C24—H24	0.965
N9—C28	1.391 (2)	C25—C26	1.384 (3)
N9—C29	1.474 (2)	C25—H25	0.970
C10—C11	1.490 (2)	C26—C27	1.387 (3)
C11—C12	1.383 (2)	C26—H26	0.958
C11—C16	1.386 (2)	C27—C28	1.394 (2)
C12—C13	1.379 (2)	C27—H27	0.964
C12—H12	0.964	C29—C30	1.518 (3)
C13—C14	1.384 (3)	C29—C31	1.521 (3)
C14—C15	1.366 (2)	C29—H29	0.971
C14—H14	0.966	C30—H30A	0.960
C15—C16	1.383 (2)	C30—H30B	0.958
C16—H16	0.978	C30—H30C	0.961
C17—C18	1.393 (3)	C31—H31A	0.976
C17—C22	1.417 (2)	C31—H31B	0.951
C18—C19	1.372 (3)	C31—H31C	0.967
C18—H18	0.969
C10—O1—H1	122 (3)	C21—C20—H20	119.3
C10—O2—H2	118 (3)	C20—C21—C22	119.1 (2)
O3—N7—O4	124.1 (2)	C20—C21—H21	120.2
O3—N7—C13	118.4 (2)	C22—C21—H21	120.6
O4—N7—C13	117.5 (2)	C17—C22—C21	119.7 (2)
O5—N8—O6	124.8 (2)	C17—C22—C23	106.6 (1)
O5—N8—C15	117.3 (2)	C21—C22—C23	133.6 (2)
O6—N8—C15	117.9 (1)	C22—C23—C24	133.6 (1)
C17—N9—C28	108.2 (1)	C22—C23—C28	107.0 (1)
C17—N9—C29	128.0 (1)	C24—C23—C28	119.3 (1)
C28—N9—C29	123.6 (1)	C23—C24—C25	119.2 (2)
O1—C10—O2	124.8 (1)	C23—C24—H24	120.3
O1—C10—C11	118.1 (1)	C25—C24—H24	120.5
O2—C10—C11	117.1 (1)	C24—C25—C26	120.9 (2)
C10—C11—C12	120.1 (1)	C24—C25—H25	120.2
C10—C11—C16	119.4 (1)	C26—C25—H25	118.8
C12—C11—C16	120.5 (1)	C25—C26—C27	121.8 (2)
C11—C12—C13	118.6 (2)	C25—C26—H26	119.1
C11—C12—H12	120.7	C27—C26—H26	119.1
C13—C12—H12	120.7	C26—C27—C28	117.3 (1)
N7—C13—C12	118.9 (2)	C26—C27—H27	121.0
N7—C13—C14	118.3 (1)	C28—C27—H27	121.7
C12—C13—C14	122.7 (1)	N9—C28—C23	109.1 (1)
C13—C14—C15	116.7 (1)	N9—C28—C27	129.4 (1)
C13—C14—H14	121.3	C23—C28—C27	121.4 (1)
C15—C14—H14	121.9	N9—C29—C30	111.6 (1)
N8—C15—C14	118.7 (1)	N9—C29—C31	112.4 (1)
N8—C15—C16	118.1 (1)	N9—C29—H29	107.3
C14—C15—C16	123.2 (2)	C30—C29—C31	112.4 (2)
C11—C16—C15	118.3 (1)	C30—C29—H29	106.9
C11—C16—H16	120.4	C31—C29—H29	105.7
C15—C16—H16	121.3	C29—C30—H30A	109.8
N9—C17—C18	130.6 (2)	C29—C30—H30B	109.1
N9—C17—C22	109.1 (1)	C29—C30—H30C	109.3
C18—C17—C22	120.3 (1)	H30A—C30—H30B	109.6
C17—C18—C19	118.4 (2)	H30A—C30—H30C	109.4
C17—C18—H18	120.4	H30B—C30—H30C	109.6
C19—C18—H18	121.2	C29—C31—H31A	109.1
C18—C19—C20	122.0 (2)	C29—C31—H31B	111.4
C18—C19—H19	120.5	C29—C31—H31C	110.3
C20—C19—H19	117.5	H31A—C31—H31B	108.8
C19—C20—C21	120.4 (2)	H31A—C31—H31C	107.5
C19—C20—H20	120.4	H31B—C31—H31C	109.6

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.78 (4)	1.86 (4)	2.629 (2)	174 (5)
O2—H2···O1^i	0.82 (4)	1.81 (4)	2.629 (2)	178 (4)

Symmetry code: (i) −x, −y, −z+2.

(III)

Crystal data

C16H17N·C7H4N2O6	Z = 4
Mr = 435.44	Dx = 1.344 Mg m^−3
Triclinic, P1	Mo Kα radiation, λ = 0.71073 Å
a = 16.723 (2) Å	Cell parameters from 25 reflections
b = 16.784 (3) Å	θ = 11.8–14.7°
c = 8.4129 (9) Å	µ = 0.10 mm^−1
α = 102.36 (1)°	T = 298 K
β = 92.34 (1)°	Prism, orange
γ = 109.91 (1)°	0.6 × 0.5 × 0.2 mm
V = 2152.0 (6) Å^3

Data collection

Rigaku AFC-7R diffractometer	θmax = 27.5°, θmin = 2.5°
θ–2θ scans	h = 0→22
10208 measured reflections	k = −22→22
9870 independent reflections	l = −11→11
4817 reflections with I > 2σ(I)	3 standard reflections every 150 reflections
Rint = 0.010	intensity decay: none

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.061	w = 1/[σ^2(Fo^2) + (0.050P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.192	(Δ/σ)max = 0.001
S = 1.74	Δρmax = 0.24 e Å^−3
9870 reflections	Δρmin = −0.25 e Å^−3
593 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.1139 (2)	0.3069 (2)	0.8584 (3)	0.0751 (8)
O1*	−0.0704 (1)	0.2143 (1)	0.5645 (3)	0.0705 (6)
O2	0.0230 (2)	0.1692 (1)	0.7635 (3)	0.0719 (6)
O2*	0.0097 (1)	0.3540 (1)	0.6844 (3)	0.0665 (5)
O3	0.0840 (2)	−0.0625 (2)	0.9435 (4)	0.125 (1)
O3*	−0.1002 (2)	0.5786 (1)	0.6063 (3)	0.0879 (7)
O4	0.1969 (2)	−0.0341 (2)	1.1044 (4)	0.123 (1)
O4*	−0.1979 (2)	0.5499 (1)	0.4060 (3)	0.1023 (8)
O5	0.4042 (2)	0.2571 (2)	1.2670 (3)	0.0994 (8)
O5*	−0.3542 (2)	0.2507 (2)	0.1185 (3)	0.0964 (7)
O6	0.3728 (2)	0.3626 (2)	1.2126 (3)	0.1074 (8)
O6*	−0.3153 (2)	0.1498 (2)	0.1733 (3)	0.0997 (8)
N7	0.1496 (2)	−0.0125 (2)	1.0244 (4)	0.0814 (8)
N7*	−0.1524 (2)	0.5285 (2)	0.4910 (3)	0.0695 (6)
N8	0.3570 (2)	0.2854 (2)	1.2035 (3)	0.0746 (7)
N8*	−0.3070 (2)	0.2259 (2)	0.1906 (3)	0.0692 (6)
N9	0.3086 (2)	0.2507 (2)	0.6347 (3)	0.0702 (7)
N9*	−0.2725 (1)	0.2366 (1)	0.7314 (3)	0.0609 (6)
C10	0.0895 (2)	0.2252 (2)	0.8477 (3)	0.0571 (7)
C10*	−0.0521 (2)	0.2969 (2)	0.5896 (3)	0.0540 (6)
C11	0.1462 (2)	0.1957 (2)	0.9426 (3)	0.0522 (6)
C11*	−0.1120 (2)	0.3247 (2)	0.4983 (3)	0.0505 (6)
C12	0.1219 (2)	0.1080 (2)	0.9414 (3)	0.0556 (6)
C12*	−0.1029 (2)	0.4123 (2)	0.5331 (3)	0.0515 (6)
C13	0.1753 (2)	0.0811 (2)	1.0266 (3)	0.0583 (7)
C13*	−0.1608 (2)	0.4366 (2)	0.4509 (3)	0.0536 (6)
C14	0.2533 (2)	0.1369 (2)	1.1121 (3)	0.0581 (7)
C14*	−0.2269 (2)	0.3776 (2)	0.3358 (3)	0.0550 (6)
C15	0.2748 (2)	0.2232 (2)	1.1109 (3)	0.0542 (6)
C15*	−0.2339 (2)	0.2919 (2)	0.3068 (3)	0.0546 (6)
C16	0.2228 (2)	0.2540 (2)	1.0285 (3)	0.0559 (6)
C16*	−0.1785 (2)	0.2632 (2)	0.3839 (3)	0.0541 (6)
C17	0.3370 (2)	0.1947 (2)	0.7003 (4)	0.0686 (8)
C17*	−0.3080 (2)	0.2944 (2)	0.6928 (3)	0.0637 (7)
C18	0.4137 (2)	0.2124 (2)	0.7987 (4)	0.089 (1)
C18*	−0.3799 (2)	0.2763 (2)	0.5781 (4)	0.087 (1)
C19	0.4264 (2)	0.1463 (4)	0.8528 (5)	0.106 (1)
C19*	−0.3987 (2)	0.3483 (4)	0.5592 (5)	0.115 (2)
C20	0.3643 (4)	0.0633 (3)	0.8107 (5)	0.108 (1)
C20*	−0.3521 (4)	0.4326 (4)	0.6504 (7)	0.127 (2)
C21	0.2882 (3)	0.0435 (2)	0.7125 (4)	0.088 (1)
C21*	−0.2842 (3)	0.4492 (2)	0.7628 (4)	0.097 (1)
C22	0.2742 (2)	0.1114 (2)	0.6555 (4)	0.0659 (8)
C22*	−0.2596 (2)	0.3792 (2)	0.7852 (4)	0.0673 (8)
C23	0.2056 (2)	0.1170 (2)	0.5561 (3)	0.0673 (8)
C23*	−0.1928 (2)	0.3717 (2)	0.8863 (3)	0.0614 (7)
C24	0.1276 (3)	0.0583 (2)	0.4748 (4)	0.094 (1)
C24*	−0.1249 (3)	0.4329 (2)	0.9997 (4)	0.087 (1)
C25	0.0752 (2)	0.0857 (4)	0.3898 (5)	0.111 (1)
C25*	−0.0700 (2)	0.4025 (3)	1.0729 (4)	0.102 (1)
C26	0.0980 (3)	0.1716 (4)	0.3830 (4)	0.108 (1)
C26*	−0.0812 (2)	0.3143 (3)	1.0379 (4)	0.093 (1)
C27	0.1752 (3)	0.2338 (2)	0.4602 (4)	0.0814 (9)
C27*	−0.1475 (2)	0.2521 (2)	0.9265 (4)	0.0700 (8)
C28	0.2288 (2)	0.2047 (2)	0.5461 (3)	0.0646 (7)
C28*	−0.2027 (2)	0.2831 (2)	0.8504 (3)	0.0562 (7)
C29	0.3612 (2)	0.3412 (2)	0.6392 (4)	0.090 (1)
C29*	−0.3014 (2)	0.1437 (2)	0.6573 (4)	0.0724 (8)
C30	0.3591 (2)	0.4080 (2)	0.7868 (3)	0.0679 (8)
C30*	−0.3724 (2)	0.0888 (2)	0.7351 (4)	0.0747 (9)
C31	0.4133 (2)	0.4993 (2)	0.7712 (4)	0.0835 (9)
C31*	−0.3984 (2)	−0.0080 (2)	0.6605 (4)	0.0860 (10)
C32	0.4164 (2)	0.5697 (2)	0.9123 (4)	0.104 (1)
C32*	−0.4633 (3)	−0.0640 (2)	0.7417 (5)	0.116 (1)
H1	0.092 (4)	0.323 (4)	0.820 (7)	0.0343 (2)*	0.50
H1*	−0.034 (3)	0.196 (3)	0.606 (7)	0.0470 (2)*	0.50
H2	−0.007 (4)	0.182 (4)	0.716 (9)	0.0661 (3)*	0.50
H2*	0.044 (5)	0.330 (4)	0.750 (8)	0.0931 (3)*	0.50
H12	0.0680	0.0660	0.8816	0.0662*
H12*	−0.0564	0.4562	0.6123	0.0589*
H14	0.2910	0.1165	1.1703	0.0675*
H14*	−0.2657	0.3970	0.2790	0.0629*
H16	0.2412	0.3165	1.0317	0.0645*
H16*	−0.1856	0.2011	0.3593	0.0616*
H18	0.4568	0.2720	0.8263	0.1002*
H18*	−0.4147	0.2167	0.5172	0.1043*
H19	0.4800	0.1572	0.9203	0.1203*
H19*	−0.4462	0.3411	0.4812	0.1297*
H20	0.3748	0.0187	0.8538	0.1320*
H20*	−0.3685	0.4798	0.6278	0.1407*
H21	0.2461	−0.0149	0.6859	0.1027*
H21*	−0.2532	0.5081	0.8263	0.1150*
H24	0.1084	−0.0031	0.4780	0.1099*
H24*	−0.1187	0.4946	1.0278	0.1026*
H25	0.0213	0.0441	0.3309	0.1259*
H25*	−0.0219	0.4438	1.1492	0.1232*
H26	0.0603	0.1898	0.3203	0.1279*
H26*	−0.0411	0.2961	1.0937	0.1085*
H27	0.1925	0.2955	0.4571	0.0975*
H27*	−0.1550	0.1903	0.9014	0.0827*
H29A	0.3419	0.3563	0.5429	0.1049*
H29B	0.4198	0.3449	0.6328	0.1049*
H29*A	−0.2532	0.1254	0.6659	0.0873*
H29*B	−0.3205	0.1350	0.5432	0.0873*
H30A	0.3017	0.4054	0.7978	0.0772*
H30B	0.3828	0.3978	0.8840	0.0772*
H30*A	−0.3561	0.1003	0.8508	0.0843*
H30*B	−0.4233	0.1047	0.7207	0.0843*
H31A	0.3898	0.5091	0.6734	0.0933*
H31B	0.4710	0.5012	0.7581	0.0933*
H31*A	−0.3469	−0.0228	0.6653	0.0978*
H31*B	−0.4196	−0.0202	0.5451	0.0978*
H32A	0.4513	0.6253	0.8958	0.1152*
H32B	0.4402	0.5608	1.0103	0.1152*
H32C	0.3593	0.5692	0.9251	0.1152*
H32*B	−0.5156	−0.0509	0.7358	0.1292*
H32*C	−0.4430	−0.0528	0.8570	0.1292*
H32*A	−0.4772	−0.1249	0.6923	0.1292*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.083 (2)	0.072 (2)	0.080 (2)	0.036 (1)	−0.006 (1)	0.028 (1)
O1*	0.079 (1)	0.069 (1)	0.074 (1)	0.042 (1)	−0.004 (1)	0.015 (1)
O2	0.066 (1)	0.074 (1)	0.078 (2)	0.028 (1)	−0.009 (1)	0.021 (1)
O2*	0.060 (1)	0.070 (1)	0.070 (1)	0.022 (1)	−0.005 (1)	0.022 (1)
O3	0.121 (2)	0.067 (2)	0.170 (3)	0.014 (2)	−0.042 (2)	0.034 (2)
O3*	0.102 (2)	0.057 (1)	0.090 (2)	0.018 (1)	−0.015 (1)	0.009 (1)
O4	0.126 (2)	0.078 (2)	0.170 (3)	0.043 (2)	−0.034 (2)	0.042 (2)
O4*	0.095 (2)	0.076 (2)	0.142 (2)	0.038 (1)	−0.023 (2)	0.036 (1)
O5	0.078 (2)	0.112 (2)	0.098 (2)	0.034 (1)	−0.029 (1)	0.010 (1)
O5*	0.080 (2)	0.106 (2)	0.089 (2)	0.031 (1)	−0.030 (1)	0.005 (1)
O6	0.104 (2)	0.081 (2)	0.112 (2)	0.005 (1)	−0.023 (2)	0.023 (1)
O6*	0.104 (2)	0.070 (2)	0.094 (2)	0.004 (1)	−0.022 (1)	0.007 (1)
N7	0.076 (2)	0.064 (2)	0.103 (2)	0.025 (2)	−0.006 (2)	0.023 (2)
N7*	0.068 (2)	0.059 (2)	0.083 (2)	0.022 (1)	0.003 (1)	0.025 (1)
N8	0.074 (2)	0.079 (2)	0.061 (2)	0.019 (2)	−0.001 (1)	0.012 (1)
N8*	0.060 (2)	0.075 (2)	0.056 (1)	0.009 (1)	0.000 (1)	0.009 (1)
N9	0.072 (2)	0.058 (1)	0.073 (2)	0.015 (1)	0.014 (1)	0.015 (1)
N9*	0.059 (1)	0.054 (1)	0.059 (1)	0.010 (1)	0.008 (1)	0.009 (1)
C10	0.065 (2)	0.062 (2)	0.053 (2)	0.030 (2)	0.009 (1)	0.018 (1)
C10*	0.060 (2)	0.060 (2)	0.049 (2)	0.027 (1)	0.009 (1)	0.016 (1)
C11	0.051 (2)	0.064 (2)	0.048 (1)	0.026 (1)	0.010 (1)	0.016 (1)
C11*	0.050 (1)	0.059 (2)	0.046 (1)	0.021 (1)	0.009 (1)	0.016 (1)
C12	0.051 (2)	0.056 (2)	0.061 (2)	0.020 (1)	0.003 (1)	0.015 (1)
C12*	0.048 (1)	0.060 (2)	0.045 (1)	0.017 (1)	0.004 (1)	0.014 (1)
C13	0.064 (2)	0.052 (2)	0.064 (2)	0.025 (1)	0.009 (1)	0.017 (1)
C13*	0.054 (2)	0.056 (2)	0.055 (2)	0.020 (1)	0.011 (1)	0.020 (1)
C14	0.063 (2)	0.067 (2)	0.054 (2)	0.033 (2)	0.008 (1)	0.016 (1)
C14*	0.046 (1)	0.070 (2)	0.053 (2)	0.021 (1)	0.006 (1)	0.023 (1)
C15	0.049 (2)	0.064 (2)	0.047 (1)	0.019 (1)	0.005 (1)	0.010 (1)
C15*	0.046 (1)	0.071 (2)	0.041 (1)	0.014 (1)	0.007 (1)	0.014 (1)
C16	0.062 (2)	0.061 (2)	0.048 (1)	0.023 (1)	0.013 (1)	0.016 (1)
C16*	0.061 (2)	0.060 (2)	0.045 (1)	0.024 (1)	0.013 (1)	0.016 (1)
C17	0.072 (2)	0.070 (2)	0.063 (2)	0.027 (2)	0.021 (2)	0.010 (2)
C17*	0.056 (2)	0.079 (2)	0.059 (2)	0.023 (2)	0.018 (1)	0.021 (2)
C18	0.073 (2)	0.116 (3)	0.080 (2)	0.039 (2)	0.018 (2)	0.017 (2)
C18*	0.061 (2)	0.131 (3)	0.077 (2)	0.037 (2)	0.015 (2)	0.036 (2)
C19	0.095 (3)	0.147 (4)	0.096 (3)	0.073 (3)	0.020 (2)	0.021 (3)
C19*	0.090 (3)	0.207 (5)	0.096 (3)	0.089 (4)	0.038 (2)	0.074 (3)
C20	0.147 (4)	0.136 (4)	0.090 (3)	0.104 (4)	0.040 (3)	0.032 (3)
C20*	0.161 (5)	0.191 (5)	0.116 (4)	0.132 (5)	0.080 (4)	0.091 (4)
C21	0.122 (3)	0.071 (2)	0.084 (2)	0.047 (2)	0.045 (2)	0.016 (2)
C21*	0.143 (4)	0.091 (3)	0.098 (3)	0.070 (3)	0.069 (3)	0.050 (2)
C22	0.077 (2)	0.060 (2)	0.061 (2)	0.029 (2)	0.023 (2)	0.008 (1)
C22*	0.082 (2)	0.068 (2)	0.060 (2)	0.031 (2)	0.032 (2)	0.022 (2)
C23	0.075 (2)	0.060 (2)	0.054 (2)	0.016 (2)	0.021 (2)	−0.001 (1)
C23*	0.075 (2)	0.050 (2)	0.049 (2)	0.008 (1)	0.022 (1)	0.010 (1)
C24	0.094 (3)	0.082 (2)	0.076 (2)	0.006 (2)	0.023 (2)	−0.001 (2)
C24*	0.096 (3)	0.073 (2)	0.058 (2)	−0.008 (2)	0.021 (2)	0.004 (2)
C25	0.081 (3)	0.147 (4)	0.067 (2)	0.011 (3)	0.003 (2)	−0.005 (3)
C25*	0.079 (3)	0.127 (3)	0.049 (2)	−0.018 (2)	0.010 (2)	0.008 (2)
C26	0.100 (3)	0.176 (5)	0.058 (2)	0.066 (3)	0.014 (2)	0.018 (3)
C26*	0.063 (2)	0.150 (4)	0.058 (2)	0.019 (2)	0.007 (2)	0.038 (2)
C27	0.098 (3)	0.100 (3)	0.063 (2)	0.052 (2)	0.025 (2)	0.024 (2)
C27*	0.071 (2)	0.085 (2)	0.059 (2)	0.026 (2)	0.019 (2)	0.030 (2)
C28	0.073 (2)	0.063 (2)	0.054 (2)	0.021 (2)	0.019 (2)	0.008 (1)
C28*	0.053 (2)	0.060 (2)	0.048 (2)	0.009 (1)	0.013 (1)	0.015 (1)
C29	0.105 (3)	0.065 (2)	0.084 (2)	0.009 (2)	0.032 (2)	0.019 (2)
C29*	0.075 (2)	0.059 (2)	0.065 (2)	0.007 (2)	0.011 (2)	0.004 (1)
C30	0.071 (2)	0.066 (2)	0.066 (2)	0.021 (2)	0.009 (1)	0.020 (1)
C30*	0.082 (2)	0.059 (2)	0.064 (2)	0.005 (2)	0.014 (2)	0.007 (1)
C31	0.085 (2)	0.066 (2)	0.087 (2)	0.012 (2)	0.011 (2)	0.017 (2)
C31*	0.081 (2)	0.069 (2)	0.084 (2)	0.004 (2)	0.006 (2)	0.007 (2)
C32	0.114 (3)	0.083 (2)	0.103 (3)	0.025 (2)	0.010 (2)	0.016 (2)
C32*	0.114 (3)	0.084 (3)	0.122 (3)	−0.001 (2)	0.003 (3)	0.030 (2)

Geometric parameters (Å, º)

O1—C10	1.272 (4)	C19*—C20*	1.391 (7)
O1—H1	0.64 (7)	C19*—H19*	0.967
O1*—C10*	1.281 (4)	C20—C21	1.385 (7)
O1*—H1*	0.86 (6)	C20—H20	0.961
O2—C10	1.249 (3)	C20*—C21*	1.359 (7)
O2—H2	0.74 (8)	C20*—H20*	0.973
O2*—C10*	1.247 (3)	C21—C22	1.410 (5)
O2*—H2*	1.01 (8)	C21—H21	0.965
O3—N7	1.199 (4)	C21*—C22*	1.416 (6)
O3*—N7*	1.221 (3)	C21*—H21*	0.966
O4—N7	1.211 (5)	C22—C23	1.433 (5)
O4*—N7*	1.214 (4)	C22*—C23*	1.432 (5)
O5—N8	1.211 (4)	C23—C24	1.380 (4)
O5*—N8*	1.207 (4)	C23—C28	1.410 (4)
O6—N8	1.215 (4)	C23*—C24*	1.398 (4)
O6*—N8*	1.211 (4)	C23*—C28*	1.401 (4)
N7—C13	1.477 (4)	C24—C25	1.361 (7)
N7*—C13*	1.463 (4)	C24—H24	0.976
N8—C15	1.475 (3)	C24*—C25*	1.375 (7)
N8*—C15*	1.482 (3)	C24*—H24*	0.978
N9—C17	1.384 (5)	C25—C26	1.374 (8)
N9—C28	1.379 (4)	C25—H25	0.965
N9—C29	1.465 (4)	C25*—C26*	1.390 (7)
N9*—C17*	1.383 (5)	C25*—H25*	0.963
N9*—C28*	1.386 (3)	C26—C27	1.379 (5)
N9*—C29*	1.448 (3)	C26—H26	0.971
C10—C11	1.487 (5)	C26*—C27*	1.379 (4)
C10*—C11*	1.489 (4)	C26*—H26*	0.970
C11—C12	1.385 (4)	C27—C28	1.400 (6)
C11—C16	1.374 (3)	C27—H27	0.983
C11*—C12*	1.390 (4)	C27*—C28*	1.399 (5)
C11*—C16*	1.391 (3)	C27*—H27*	0.977
C12—C13	1.369 (4)	C29—C30	1.495 (4)
C12—H12	0.969	C29—H29A	0.972
C12*—C13*	1.384 (4)	C29—H29B	0.966
C12*—H12*	0.973	C29*—C30*	1.504 (4)
C13—C14	1.379 (3)	C29*—H29*A	0.960
C13*—C14*	1.377 (3)	C29*—H29*B	0.964
C14—C15	1.370 (4)	C30—C31	1.529 (4)
C14—H14	0.974	C30—H30A	0.955
C14*—C15*	1.369 (4)	C30—H30B	0.967
C14*—H14*	0.971	C30*—C31*	1.512 (4)
C15—C16	1.384 (4)	C30*—H30*A	0.960
C15*—C16*	1.379 (4)	C30*—H30*B	0.985
C16—H16	0.981	C31—C32	1.471 (4)
C16*—H16*	0.981	C31—H31A	0.966
C17—C18	1.403 (5)	C31—H31B	0.967
C17—C22	1.394 (4)	C31*—C32*	1.472 (5)
C17*—C18*	1.414 (4)	C31*—H31*A	0.976
C17*—C22*	1.406 (4)	C31*—H31*B	0.974
C18—C19	1.361 (7)	C32—H32A	0.960
C18—H18	0.984	C32—H32B	0.963
C18*—C19*	1.386 (8)	C32—H32C	0.962
C18*—H18*	0.980	C32*—H32*B	0.975
C19—C20	1.386 (6)	C32*—H32*C	0.971
C19—H19	0.981	C32*—H32*A	0.958
C10—O1—H1	121 (4)	C20*—C21*—H21*	120.3
C10*—O1*—H1*	118 (3)	C22*—C21*—H21*	120.7
C10—O2—H2	121 (4)	C17—C22—C21	118.8 (3)
C10*—O2*—H2*	114 (3)	C17—C22—C23	106.8 (3)
O3—N7—O4	123.9 (3)	C21—C22—C23	134.4 (3)
O3—N7—C13	118.7 (3)	C17*—C22*—C21*	118.5 (3)
O4—N7—C13	117.4 (2)	C17*—C22*—C23*	106.7 (3)
O3*—N7*—O4*	124.3 (3)	C21*—C22*—C23*	134.8 (2)
O3*—N7*—C13*	118.4 (3)	C22—C23—C24	134.8 (3)
O4*—N7*—C13*	117.3 (2)	C22—C23—C28	107.3 (2)
O5—N8—O6	124.0 (2)	C24—C23—C28	117.9 (3)
O5—N8—C15	118.5 (3)	C22*—C23*—C24*	132.9 (3)
O6—N8—C15	117.5 (3)	C22*—C23*—C28*	106.9 (2)
O5*—N8*—O6*	124.1 (2)	C24*—C23*—C28*	120.1 (3)
O5*—N8*—C15*	118.5 (3)	C23—C24—C25	120.1 (3)
O6*—N8*—C15*	117.5 (3)	C23—C24—H24	121.2
C17—N9—C28	109.4 (2)	C25—C24—H24	118.7
C17—N9—C29	124.4 (2)	C23*—C24*—C25*	117.4 (3)
C28—N9—C29	125.6 (3)	C23*—C24*—H24*	120.4
C17*—N9*—C28*	108.3 (2)	C25*—C24*—H24*	122.1
C17*—N9*—C29*	126.0 (2)	C24—C25—C26	121.4 (3)
C28*—N9*—C29*	125.6 (3)	C24—C25—H25	119.8
O1—C10—O2	125.2 (3)	C26—C25—H25	118.7
O1—C10—C11	116.3 (2)	C24*—C25*—C26*	121.9 (3)
O2—C10—C11	118.5 (3)	C24*—C25*—H25*	118.9
O1*—C10*—O2*	125.5 (3)	C26*—C25*—H25*	119.2
O1*—C10*—C11*	115.7 (2)	C25—C26—C27	121.7 (5)
O2*—C10*—C11*	118.8 (3)	C25—C26—H26	120.3
C10—C11—C12	119.3 (2)	C27—C26—H26	118.0
C10—C11—C16	120.8 (3)	C25*—C26*—C27*	122.2 (4)
C12—C11—C16	119.9 (3)	C25*—C26*—H26*	118.8
C10*—C11*—C12*	119.4 (2)	C27*—C26*—H26*	119.1
C10*—C11*—C16*	120.4 (2)	C26—C27—C28	116.4 (4)
C12*—C11*—C16*	120.2 (3)	C26—C27—H27	122.9
C11—C12—C13	118.9 (2)	C28—C27—H27	120.8
C11—C12—H12	120.9	C26*—C27*—C28*	116.0 (3)
C13—C12—H12	120.2	C26*—C27*—H27*	122.1
C11*—C12*—C13*	118.6 (2)	C28*—C27*—H27*	121.9
C11*—C12*—H12*	121.1	N9—C28—C23	107.7 (3)
C13*—C12*—H12*	120.2	N9—C28—C27	129.8 (3)
N7—C13—C12	118.8 (2)	C23—C28—C27	122.5 (3)
N7—C13—C14	117.9 (3)	N9*—C28*—C23*	109.0 (3)
C12—C13—C14	123.3 (3)	N9*—C28*—C27*	128.6 (2)
N7*—C13*—C12*	118.5 (2)	C23*—C28*—C27*	122.4 (2)
N7*—C13*—C14*	118.8 (3)	N9—C29—C30	115.5 (3)
C12*—C13*—C14*	122.8 (3)	N9—C29—H29A	108.5
C13—C14—C15	116.0 (3)	N9—C29—H29B	108.4
C13—C14—H14	122.2	C30—C29—H29A	107.7
C15—C14—H14	121.8	C30—C29—H29B	108.5
C13*—C14*—C15*	116.6 (3)	H29A—C29—H29B	107.9
C13*—C14*—H14*	120.6	N9*—C29*—C30*	114.4 (3)
C15*—C14*—H14*	122.8	N9*—C29*—H29*A	107.9
N8—C15—C14	117.8 (3)	N9*—C29*—H29*B	107.5
N8—C15—C16	119.1 (3)	C30*—C29*—H29*A	108.5
C14—C15—C16	123.1 (2)	C30*—C29*—H29*B	109.4
N8*—C15*—C14*	118.2 (3)	H29*A—C29*—H29*B	109.1
N8*—C15*—C16*	118.1 (3)	C29—C30—C31	109.8 (2)
C14*—C15*—C16*	123.7 (2)	C29—C30—H30A	110.6
C11—C16—C15	118.8 (2)	C29—C30—H30B	109.7
C11—C16—H16	121.5	C31—C30—H30A	109.0
C15—C16—H16	119.7	C31—C30—H30B	108.3
C11*—C16*—C15*	118.1 (2)	H30A—C30—H30B	109.3
C11*—C16*—H16*	120.7	C29*—C30*—C31*	113.2 (3)
C15*—C16*—H16*	121.2	C29*—C30*—H30*A	110.4
N9—C17—C18	129.5 (3)	C29*—C30*—H30*B	109.0
N9—C17—C22	108.7 (3)	C31*—C30*—H30*A	109.1
C18—C17—C22	121.8 (3)	C31*—C30*—H30*B	107.6
N9*—C17*—C18*	128.2 (3)	H30*A—C30*—H30*B	107.4
N9*—C17*—C22*	109.0 (3)	C30—C31—C32	113.9 (3)
C18*—C17*—C22*	122.8 (3)	C30—C31—H31A	108.2
C17—C18—C19	118.9 (3)	C30—C31—H31B	108.5
C17—C18—H18	119.3	C32—C31—H31A	108.9
C19—C18—H18	121.9	C32—C31—H31B	108.9
C17*—C18*—C19*	115.6 (3)	H31A—C31—H31B	108.4
C17*—C18*—H18*	122.2	C30*—C31*—C32*	114.6 (3)
C19*—C18*—H18*	122.2	C30*—C31*—H31*A	107.6
C18—C19—C20	120.1 (4)	C30*—C31*—H31*B	108.9
C18—C19—H19	120.0	C32*—C31*—H31*A	109.0
C20—C19—H19	119.9	C32*—C31*—H31*B	109.3
C18*—C19*—C20*	122.5 (5)	H31*A—C31*—H31*B	107.1
C18*—C19*—H19*	120.3	C31—C32—H32A	110.1
C20*—C19*—H19*	117.1	C31—C32—H32B	109.5
C19—C20—C21	122.5 (5)	C31—C32—H32C	109.5
C19—C20—H20	117.7	H32A—C32—H32B	109.2
C21—C20—H20	119.8	H32A—C32—H32C	109.3
C19*—C20*—C21*	121.5 (6)	H32B—C32—H32C	109.1
C19*—C20*—H20*	117.5	C31*—C32*—H32*B	109.9
C21*—C20*—H20*	120.9	C31*—C32*—H32*C	110.3
C20—C21—C22	118.0 (3)	C31*—C32*—H32*A	112.1
C20—C21—H21	120.4	H32*B—C32*—H32*C	107.3
C22—C21—H21	121.5	H32*B—C32*—H32*A	108.3
C20*—C21*—C22*	119.0 (3)	H32*C—C32*—H32*A	108.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2*	0.64 (7)	2.02 (7)	2.651 (4)	171 (6)
O1*—H1*···O2	0.86 (6)	1.82 (6)	2.637 (4)	158 (5)
O2—H2···O1*	0.74 (8)	1.90 (8)	2.637 (4)	169 (8)
O2*—H2*···O1	1.01 (8)	1.65 (8)	2.651 (4)	170 (6)

(IV)

Crystal data

C16H17N·C7H4N2O6	Dx = 1.364 Mg m^−3
Mr = 435.44	Mo Kα radiation, λ = 0.71073 Å
Monoclinic, P21/c	Cell parameters from 25 reflections
a = 8.212 (2) Å	θ = 12.3–14.7°
b = 31.924 (2) Å	µ = 0.10 mm^−1
c = 8.438 (1) Å	T = 298 K
β = 106.54 (1)°	Prism, orange
V = 2120.5 (6) Å^3	0.5 × 0.4 × 0.3 mm
Z = 4

Data collection

Rigaku AFC-7R diffractometer	θmax = 27.5°, θmin = 2.5°
ω scans	h = −11→11
5184 measured reflections	k = 0→41
4864 independent reflections	l = −11→0
2811 reflections with I > 2σ(I)	3 standard reflections every 150 reflections
Rint = 0.006	intensity decay: none

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0409P)^2 + 1.8479P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.049	(Δ/σ)max = 0.001
wR(F^2) = 0.165	Δρmax = 0.20 e Å^−3
S = 1.03	Δρmin = −0.25 e Å^−3
4864 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
298 parameters	Extinction coefficient: 0.0044 (7)
H atoms treated by a mixture of independent and constrained refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.6288 (3)	0.45743 (7)	−0.0189 (3)	0.0671 (6)
O2	0.6442 (3)	0.50128 (7)	0.1912 (3)	0.0699 (6)
O3	0.9712 (4)	0.4595 (1)	0.7416 (3)	0.1084 (10)
O4	1.1433 (5)	0.40767 (9)	0.7761 (3)	0.126 (1)
O5	1.1618 (3)	0.32148 (7)	0.3129 (3)	0.0873 (7)
O6	0.9912 (3)	0.33483 (8)	0.0721 (3)	0.0851 (7)
N7	1.0354 (4)	0.43026 (9)	0.6898 (3)	0.0793 (8)
N8	1.0544 (3)	0.34276 (7)	0.2182 (4)	0.0639 (6)
N9	0.5426 (3)	0.34977 (7)	0.2175 (3)	0.0560 (6)
C10	0.6893 (4)	0.46903 (8)	0.1302 (3)	0.0538 (6)
C11	0.8202 (3)	0.44159 (8)	0.2400 (3)	0.0509 (6)
C12	0.8718 (4)	0.44946 (8)	0.4092 (3)	0.0557 (7)
C13	0.9849 (4)	0.42230 (9)	0.5103 (3)	0.0565 (7)
C14	1.0490 (3)	0.38745 (8)	0.4520 (3)	0.0581 (7)
C15	0.9941 (3)	0.38056 (8)	0.2846 (3)	0.0532 (6)
C16	0.8814 (3)	0.40684 (8)	0.1767 (3)	0.0532 (6)
C17	0.6518 (4)	0.33008 (9)	0.3521 (3)	0.0581 (7)
C18	0.7513 (4)	0.2947 (1)	0.3567 (4)	0.0702 (8)
C19	0.8561 (4)	0.2825 (1)	0.5092 (5)	0.085 (1)
C20	0.8614 (4)	0.3042 (1)	0.6531 (4)	0.089 (1)
C21	0.7607 (4)	0.3388 (1)	0.6492 (4)	0.079 (1)
C22	0.6543 (4)	0.3521 (1)	0.4974 (3)	0.0615 (7)
C23	0.5408 (4)	0.3871 (1)	0.4471 (3)	0.0617 (7)
C24	0.4940 (5)	0.4209 (1)	0.5301 (4)	0.0768 (10)
C25	0.3856 (5)	0.4505 (1)	0.4420 (5)	0.085 (1)
C26	0.3198 (4)	0.44778 (9)	0.2709 (5)	0.0788 (10)
C27	0.3625 (4)	0.41464 (9)	0.1836 (3)	0.0649 (8)
C28	0.4746 (4)	0.38472 (9)	0.2734 (3)	0.0564 (7)
C29	0.5275 (3)	0.34156 (7)	0.0433 (3)	0.0547 (7)
C30	0.3687 (3)	0.31808 (8)	−0.0511 (3)	0.0499 (6)
C31	0.3676 (3)	0.31583 (8)	−0.2309 (3)	0.0665 (8)
C32	0.3584 (4)	0.27506 (9)	0.0194 (3)	0.0721 (9)
H1	0.559 (9)	0.473 (2)	−0.076 (8)	0.0595 (2)*	0.50
H2	0.56 (1)	0.517 (3)	0.130 (10)	0.1044 (4)*	0.50
H12	0.8323	0.4738	0.4548	0.0629*
H14	1.1304	0.3693	0.5249	0.0655*
H16	0.8478	0.4010	0.0597	0.0603*
H18	0.7487	0.2789	0.2594	0.0808*
H19	0.9276	0.2584	0.5178	0.0974*
H20	0.9390	0.2956	0.7581	0.0988*
H21	0.7596	0.3535	0.7498	0.0882*
H24	0.5361	0.4231	0.6480	0.0898*
H25	0.3536	0.4738	0.4982	0.0940*
H26	0.2410	0.4692	0.2111	0.0941*
H27	0.3170	0.4127	0.0647	0.0711*
H29A	0.5303	0.3680	−0.0124	0.0618*
H29B	0.6246	0.3252	0.0373	0.0618*
H30	0.2716	0.3343	−0.0452	0.0549*
H31A	0.3679	0.3434	−0.2763	0.0742*
H31B	0.4659	0.3007	−0.2407	0.0742*
H31C	0.2668	0.3012	−0.2947	0.0742*
H32A	0.3607	0.2772	0.1339	0.0832*
H32B	0.4529	0.2581	0.0114	0.0832*
H32C	0.2542	0.2614	−0.0408	0.0832*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.073 (1)	0.070 (1)	0.052 (1)	0.016 (1)	0.007 (1)	0.003 (1)
O2	0.074 (1)	0.059 (1)	0.069 (1)	0.015 (1)	0.007 (1)	−0.004 (1)
O3	0.127 (2)	0.123 (2)	0.066 (2)	0.028 (2)	0.011 (1)	−0.024 (2)
O4	0.186 (3)	0.092 (2)	0.064 (2)	0.042 (2)	−0.022 (2)	0.003 (1)
O5	0.093 (2)	0.070 (1)	0.095 (2)	0.031 (1)	0.022 (1)	0.012 (1)
O6	0.088 (2)	0.089 (2)	0.075 (2)	0.017 (1)	0.016 (1)	−0.021 (1)
N7	0.102 (2)	0.068 (2)	0.057 (2)	0.002 (2)	0.004 (2)	−0.002 (1)
N8	0.062 (2)	0.055 (1)	0.077 (2)	0.005 (1)	0.024 (1)	0.001 (1)
N9	0.066 (1)	0.057 (1)	0.044 (1)	−0.007 (1)	0.015 (1)	−0.008 (1)
C10	0.058 (2)	0.049 (1)	0.052 (2)	0.001 (1)	0.013 (1)	0.001 (1)
C11	0.050 (1)	0.047 (1)	0.054 (2)	−0.004 (1)	0.012 (1)	0.003 (1)
C12	0.061 (2)	0.047 (1)	0.058 (2)	−0.003 (1)	0.014 (1)	−0.003 (1)
C13	0.064 (2)	0.053 (2)	0.047 (1)	−0.006 (1)	0.008 (1)	0.002 (1)
C14	0.062 (2)	0.047 (1)	0.060 (2)	−0.002 (1)	0.008 (1)	0.008 (1)
C15	0.054 (2)	0.046 (1)	0.059 (2)	−0.004 (1)	0.015 (1)	0.001 (1)
C16	0.054 (2)	0.051 (1)	0.053 (1)	−0.004 (1)	0.013 (1)	0.002 (1)
C17	0.057 (2)	0.065 (2)	0.054 (2)	−0.013 (1)	0.018 (1)	−0.003 (1)
C18	0.068 (2)	0.077 (2)	0.066 (2)	−0.004 (2)	0.020 (2)	0.001 (2)
C19	0.069 (2)	0.097 (3)	0.089 (3)	0.007 (2)	0.024 (2)	0.016 (2)
C20	0.069 (2)	0.128 (3)	0.065 (2)	−0.007 (2)	0.012 (2)	0.018 (2)
C21	0.070 (2)	0.115 (3)	0.052 (2)	−0.020 (2)	0.019 (2)	−0.002 (2)
C22	0.059 (2)	0.080 (2)	0.047 (2)	−0.020 (2)	0.018 (1)	−0.008 (1)
C23	0.068 (2)	0.069 (2)	0.054 (2)	−0.025 (2)	0.025 (1)	−0.016 (1)
C24	0.087 (2)	0.084 (2)	0.069 (2)	−0.028 (2)	0.037 (2)	−0.031 (2)
C25	0.102 (3)	0.068 (2)	0.100 (3)	−0.021 (2)	0.052 (2)	−0.032 (2)
C26	0.087 (2)	0.056 (2)	0.103 (3)	−0.011 (2)	0.042 (2)	−0.011 (2)
C27	0.075 (2)	0.054 (2)	0.068 (2)	−0.014 (1)	0.024 (2)	−0.004 (1)
C28	0.068 (2)	0.052 (2)	0.053 (2)	−0.017 (1)	0.023 (1)	−0.012 (1)
C29	0.064 (2)	0.056 (2)	0.047 (1)	−0.010 (1)	0.021 (1)	−0.009 (1)
C30	0.054 (1)	0.045 (1)	0.052 (1)	−0.001 (1)	0.016 (1)	−0.008 (1)
C31	0.075 (2)	0.069 (2)	0.054 (2)	−0.003 (2)	0.014 (1)	−0.014 (1)
C32	0.085 (2)	0.053 (2)	0.077 (2)	−0.015 (2)	0.020 (2)	−0.004 (1)

Geometric parameters (Å, º)

O1—C10	1.269 (3)	C19—H19	0.959
O1—H1	0.80 (6)	C20—C21	1.374 (6)
O2—C10	1.253 (4)	C20—H20	0.972
O2—H2	0.90 (8)	C21—C22	1.396 (4)
O3—N7	1.212 (4)	C21—H21	0.972
O4—N7	1.212 (4)	C22—C23	1.437 (4)
O5—N8	1.215 (3)	C23—C24	1.398 (5)
O6—N8	1.220 (4)	C23—C28	1.413 (4)
N7—C13	1.473 (4)	C24—C25	1.364 (5)
N8—C15	1.474 (4)	C24—H24	0.958
N9—C17	1.382 (3)	C25—C26	1.392 (5)
N9—C28	1.389 (4)	C25—H25	0.960
N9—C29	1.464 (4)	C26—C27	1.390 (5)
C10—C11	1.488 (3)	C26—H26	0.978
C11—C12	1.391 (4)	C27—C28	1.391 (4)
C11—C16	1.386 (4)	C27—H27	0.968
C12—C13	1.375 (4)	C29—C30	1.519 (3)
C12—H12	0.965	C29—H29A	0.969
C13—C14	1.380 (4)	C29—H29B	0.966
C14—C15	1.373 (4)	C30—C31	1.516 (4)
C14—H14	0.963	C30—C32	1.509 (4)
C15—C16	1.382 (3)	C30—H30	0.963
C16—H16	0.965	C31—H31A	0.961
C17—C18	1.388 (4)	C31—H31B	0.964
C17—C22	1.409 (4)	C31—H31C	0.969
C18—C19	1.385 (4)	C32—H32A	0.963
C18—H18	0.959	C32—H32B	0.964
C19—C20	1.388 (6)	C32—H32C	0.966
C10—O1—H1	116 (5)	C22—C21—H21	119.7
C10—O2—H2	120 (5)	C17—C22—C21	119.8 (3)
O3—N7—O4	124.0 (3)	C17—C22—C23	106.5 (2)
O3—N7—C13	118.7 (3)	C21—C22—C23	133.7 (3)
O4—N7—C13	117.3 (3)	C22—C23—C24	134.3 (3)
O5—N8—O6	124.7 (3)	C22—C23—C28	106.9 (3)
O5—N8—C15	117.9 (3)	C24—C23—C28	118.7 (3)
O6—N8—C15	117.5 (2)	C23—C24—C25	119.4 (3)
C17—N9—C28	108.4 (2)	C23—C24—H24	120.5
C17—N9—C29	126.4 (2)	C25—C24—H24	120.0
C28—N9—C29	123.9 (2)	C24—C25—C26	121.5 (3)
O1—C10—O2	124.7 (2)	C24—C25—H25	119.8
O1—C10—C11	117.0 (2)	C26—C25—H25	118.7
O2—C10—C11	118.3 (2)	C25—C26—C27	120.9 (3)
C10—C11—C12	119.2 (2)	C25—C26—H26	119.8
C10—C11—C16	120.5 (2)	C27—C26—H26	119.3
C12—C11—C16	120.1 (2)	C26—C27—C28	117.5 (3)
C11—C12—C13	118.5 (3)	C26—C27—H27	121.2
C11—C12—H12	121.1	C28—C27—H27	121.3
C13—C12—H12	120.4	N9—C28—C23	108.7 (2)
N7—C13—C12	118.1 (3)	N9—C28—C27	129.4 (2)
N7—C13—C14	118.8 (2)	C23—C28—C27	121.9 (3)
C12—C13—C14	123.1 (2)	N9—C29—C30	115.4 (2)
C13—C14—C15	116.7 (2)	N9—C29—H29A	108.9
C13—C14—H14	121.6	N9—C29—H29B	108.3
C15—C14—H14	121.7	C30—C29—H29A	108.1
N8—C15—C14	118.3 (2)	C30—C29—H29B	107.7
N8—C15—C16	118.8 (2)	H29A—C29—H29B	108.2
C14—C15—C16	122.9 (3)	C29—C30—C31	107.9 (2)
C11—C16—C15	118.7 (2)	C29—C30—C32	112.2 (2)
C11—C16—H16	121.4	C29—C30—H30	107.9
C15—C16—H16	119.9	C31—C30—C32	111.5 (2)
N9—C17—C18	129.2 (3)	C31—C30—H30	107.9
N9—C17—C22	109.4 (2)	C32—C30—H30	109.1
C18—C17—C22	121.3 (2)	C30—C31—H31A	110.8
C17—C18—C19	117.4 (3)	C30—C31—H31B	110.1
C17—C18—H18	122.4	C30—C31—H31C	109.8
C19—C18—H18	120.2	H31A—C31—H31B	109.1
C18—C19—C20	121.8 (3)	H31A—C31—H31C	108.6
C18—C19—H19	120.1	H31B—C31—H31C	108.4
C20—C19—H19	118.0	C30—C32—H32A	110.2
C19—C20—C21	120.8 (3)	C30—C32—H32B	110.2
C19—C20—H20	120.3	C30—C32—H32C	110.2
C21—C20—H20	118.9	H32A—C32—H32B	108.9
C20—C21—C22	118.8 (3)	H32A—C32—H32C	108.7
C20—C21—H21	121.5	H32B—C32—H32C	108.6

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.80 (6)	1.87 (7)	2.650 (3)	165 (8)
O2—H2···O1^i	0.90 (8)	1.76 (8)	2.650 (3)	171 (9)

Symmetry code: (i) −x+1, −y+1, −z.