Salts of 3,5-dinitrobenzoic acid with organic diamines: hydrogen-bonded supramolecular ­structures in one, two and three dimensions

The trigonally trisubstituted carboxylic acid 3,5-dinitrobenzoic acid, (O₂N)₂C₆H₃COOH, forms 2:1 salts with a range of organic diamines L, with the general composition [LH₂]²⁺·[{(O₂N)₂C₆H₃COO}⁻]₂. When L is a bis-tertiary amine the hard N—H...O hydrogen bonds generate finite three-component aggregates, anion...cation...anion, and these aggregates are further linked by soft C—H...O hydrogen bonds to form one-dimensional molecular ladders when L is N,N,N′,N′′-tetramethyl-1,2-diaminoethane and chains of rings when L is 4,4′-dipyridylethane or 4,4′-dipyridylethene; two-dimensional sheets are formed when L is 1,4-diazabicyclo[2.2.2]octane and a three-dimensional framework is formed when L is N,N′-dimethylpiperazine. When L is the bis-secondary amine piperazine, the hard N—­H...O and soft C—H...O hydrogen bonds each generate continuous motifs in the form of distinct chains of rings, the combination of which generates sheets, while when L is the bis-primary amine 1,2-diaminoethane the hard N—H...O hydrogen bonds alone generate a three-dimensional framework.

S1. Comment

In full text version

S2. Experimental

In full text version

S3. Refinement

In full text version

Computing details

For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a). Program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997b) for (1), (4), (5), (6), (7); SHELXL97 (Sheldrick, 1997b) for (2), (3). Molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 2000) for (1), (4), (5), (6), (7); ORTEP (Johnson, 1976), PLATON (Spek, 2000) for (2), (3). Software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999) for (1), (4), (5), (6), (7); SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999) for (2), (3).

Figures

In full text version

(1) 3,5-Dinitrobenzoic acid–1,2-diaminoethane (2/1)

Crystal data

2(C7H3N2O6)·C2H10N2	F(000) = 500
Mr = 484.35	Dx = 1.590 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.4549 (2) Å	Cell parameters from 8774 reflections
b = 10.6869 (4) Å	θ = 3.0–27.5°
c = 17.4420 (6) Å	µ = 0.14 mm^−1
β = 95.704 (2)°	T = 150 K
V = 1011.76 (6) Å^3	Block, colourless
Z = 2	0.26 × 0.23 × 0.16 mm

Data collection

Kappa-CCD diffractometer	2309 independent reflections
Radiation source: fine-focus sealed X-ray tube	1919 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ϕ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→7
Tmin = 0.965, Tmax = 0.978	k = 0→13
8774 measured reflections	l = −22→22

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.0533P)^2 + 0.3986P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2309 reflections	Δρmax = 0.24 e Å^−3
156 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (5)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
O1	1.1540 (2)	0.26491 (11)	0.00743 (7)	0.0348 (3)
O2	0.9712 (2)	0.14459 (11)	0.09017 (8)	0.0396 (3)
O3	0.4260 (2)	0.36669 (11)	0.25531 (7)	0.0304 (3)
O4	0.4875 (2)	0.56298 (11)	0.28034 (7)	0.0333 (3)
O5	1.1059 (2)	0.79136 (10)	0.15939 (7)	0.0280 (3)
O6	1.3730 (2)	0.68776 (11)	0.10037 (7)	0.0328 (3)
N3	0.5367 (2)	0.46554 (13)	0.24808 (7)	0.0238 (3)
N5	1.1834 (2)	0.69420 (12)	0.13292 (7)	0.0233 (3)
C11	0.9731 (3)	0.36313 (14)	0.10844 (8)	0.0210 (3)
C12	0.7887 (3)	0.35920 (14)	0.15847 (8)	0.0221 (3)
C13	0.7360 (3)	0.46772 (14)	0.19701 (8)	0.0212 (3)
C14	0.8602 (3)	0.57947 (14)	0.19046 (8)	0.0216 (3)
C15	1.0430 (3)	0.57858 (13)	0.14075 (8)	0.0204 (3)
C16	1.0994 (3)	0.47433 (14)	0.09905 (8)	0.0211 (3)
C17	1.0371 (3)	0.24677 (14)	0.06512 (9)	0.0250 (3)
N1	0.2893 (2)	0.42624 (12)	0.42195 (7)	0.0216 (3)
C1	0.5232 (3)	0.47636 (15)	0.46048 (8)	0.0235 (3)
H12	0.7015	0.2839	0.1659	0.026*
H14	0.8225	0.6522	0.2183	0.026*
H16	1.2230	0.4785	0.0644	0.025*
H1A	0.2331	0.3640	0.4512	0.032*
H1B	0.3159	0.3954	0.3749	0.032*
H1C	0.1754	0.4886	0.4162	0.032*
H1D	0.5837	0.5455	0.4296	0.028*
H1E	0.6500	0.4098	0.4653	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0509 (8)	0.0276 (7)	0.0278 (6)	0.0082 (5)	0.0125 (5)	−0.0039 (5)
O2	0.0417 (7)	0.0200 (6)	0.0599 (9)	−0.0050 (5)	0.0184 (6)	−0.0071 (6)
O3	0.0281 (6)	0.0322 (7)	0.0320 (6)	−0.0042 (5)	0.0085 (5)	0.0034 (5)
O4	0.0396 (7)	0.0317 (7)	0.0310 (6)	0.0054 (5)	0.0156 (5)	−0.0029 (5)
O5	0.0316 (6)	0.0184 (6)	0.0335 (6)	0.0013 (4)	0.0011 (5)	−0.0032 (4)
O6	0.0292 (6)	0.0263 (6)	0.0452 (7)	−0.0018 (5)	0.0148 (5)	0.0035 (5)
N3	0.0233 (6)	0.0278 (7)	0.0206 (6)	0.0019 (5)	0.0037 (5)	0.0034 (5)
N5	0.0249 (6)	0.0193 (7)	0.0258 (6)	0.0003 (5)	0.0024 (5)	0.0016 (5)
C11	0.0231 (7)	0.0190 (7)	0.0205 (7)	0.0018 (5)	0.0010 (5)	−0.0007 (5)
C12	0.0231 (7)	0.0187 (7)	0.0243 (7)	−0.0007 (5)	0.0021 (5)	0.0013 (6)
C13	0.0213 (7)	0.0248 (8)	0.0179 (7)	0.0023 (6)	0.0046 (5)	0.0016 (5)
C14	0.0245 (7)	0.0196 (7)	0.0208 (7)	0.0030 (6)	0.0023 (5)	−0.0017 (5)
C15	0.0218 (7)	0.0169 (7)	0.0226 (7)	−0.0010 (5)	0.0020 (5)	0.0020 (5)
C16	0.0227 (7)	0.0221 (8)	0.0190 (6)	0.0027 (5)	0.0038 (5)	0.0005 (5)
C17	0.0242 (8)	0.0214 (8)	0.0290 (8)	0.0025 (6)	0.0008 (6)	−0.0052 (6)
N1	0.0250 (6)	0.0194 (6)	0.0209 (6)	−0.0030 (5)	0.0051 (5)	−0.0008 (5)
C1	0.0231 (7)	0.0258 (8)	0.0222 (7)	−0.0033 (6)	0.0060 (5)	−0.0039 (6)

Geometric parameters (Å, º)

O1—C17	1.259 (2)	C13—C14	1.383 (2)
O2—C17	1.243 (2)	C14—C15	1.385 (2)
O3—N3	1.2295 (17)	C14—H14	0.95
O4—N3	1.2260 (17)	C15—C16	1.382 (2)
O5—N5	1.2284 (17)	C16—H16	0.95
O6—N5	1.2301 (16)	N1—C1	1.4818 (18)
N3—C13	1.4725 (18)	N1—H1A	0.91
N5—C15	1.4674 (19)	N1—H1B	0.91
C11—C16	1.392 (2)	N1—H1C	0.91
C11—C12	1.396 (2)	C1—C1^i	1.513 (3)
C11—C17	1.514 (2)	C1—H1D	0.99
C12—C13	1.385 (2)	C1—H1E	0.99
C12—H12	0.95
O4—N3—O3	123.39 (12)	C14—C15—N5	117.88 (13)
O4—N3—C13	118.22 (12)	C15—C16—C11	119.19 (13)
O3—N3—C13	118.38 (12)	C15—C16—H16	120.4
O5—N5—O6	123.88 (13)	C11—C16—H16	120.4
O5—N5—C15	118.31 (12)	O2—C17—O1	127.14 (14)
O6—N5—C15	117.81 (12)	O2—C17—C11	117.20 (14)
C16—C11—C12	119.69 (13)	O1—C17—C11	115.65 (13)
C16—C11—C17	120.08 (13)	C1—N1—H1A	109.5
C12—C11—C17	120.24 (13)	C1—N1—H1B	109.5
C13—C12—C11	118.38 (13)	H1A—N1—H1B	109.5
C13—C12—H12	120.8	C1—N1—H1C	109.5
C11—C12—H12	120.8	H1A—N1—H1C	109.5
C14—C13—C12	123.78 (13)	H1B—N1—H1C	109.5
C14—C13—N3	117.43 (13)	N1—C1—C1^i	108.62 (14)
C12—C13—N3	118.79 (13)	N1—C1—H1D	110.0
C13—C14—C15	115.77 (13)	C1^i—C1—H1D	110.0
C13—C14—H14	122.1	N1—C1—H1E	110.0
C15—C14—H14	122.1	C1^i—C1—H1E	110.0
C16—C15—C14	123.16 (13)	H1D—C1—H1E	108.3
C16—C15—N5	118.95 (12)
C16—C11—C12—C13	0.5 (2)	O5—N5—C15—C16	167.74 (13)
C17—C11—C12—C13	180.0 (3)	O6—N5—C15—C16	−12.6 (2)
C11—C12—C13—C14	−1.8 (2)	O5—N5—C15—C14	−12.7 (2)
C11—C12—C13—N3	178.16 (13)	O6—N5—C15—C14	166.99 (13)
O4—N3—C13—C14	1.84 (19)	C14—C15—C16—C11	−1.9 (2)
O3—N3—C13—C14	−179.20 (13)	N5—C15—C16—C11	177.62 (12)
O4—N3—C13—C12	−178.14 (13)	C12—C11—C16—C15	1.2 (2)
O3—N3—C13—C12	0.8 (2)	C17—C11—C16—C15	−178.19 (13)
C12—C13—C14—C15	1.2 (2)	C16—C11—C17—O2	160.80 (14)
N3—C13—C14—C15	−178.76 (12)	C12—C11—C17—O2	−18.6 (2)
C13—C14—C15—C16	0.7 (2)	C16—C11—C17—O1	−18.7 (2)
C13—C14—C15—N5	−178.84 (12)	C12—C11—C17—O1	161.83 (14)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^ii	0.91	1.77	2.676 (2)	174
N1—H1B···O3	0.91	2.25	3.137 (2)	166
N1—H1C···O2^iii	0.91	1.85	2.729 (2)	163

Symmetry codes: (ii) x−1, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+1/2.

(2) 3,5-Dinitrobenzoic acid–piperazine (2/1)

Crystal data

2(C7H3N2O6)·C4H12N2	Z = 1
Mr = 510.38	F(000) = 264
Triclinic, P1	Dx = 1.539 Mg m^−3
a = 6.6970 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1655 (8) Å	Cell parameters from 2481 reflections
c = 10.5942 (9) Å	θ = 2.6–27.5°
α = 65.338 (3)°	µ = 0.13 mm^−1
β = 85.985 (4)°	T = 100 K
γ = 69.313 (3)°	Block, colourless
V = 550.57 (8) Å^3	0.17 × 0.13 × 0.08 mm

Data collection

Kappa-CCD diffractometer	2481 independent reflections
Radiation source: fine-focus sealed X-ray tube	1725 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ϕ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→8
Tmin = 0.978, Tmax = 0.990	k = −10→11
2481 measured reflections	l = −13→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0319P)^2 + 0.0563P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2481 reflections	Δρmax = 0.27 e Å^−3
164 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (6)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

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

	x	y	z	Uiso*/Ueq
O1	0.01781 (19)	0.47814 (15)	0.72943 (12)	0.0312 (3)
O2	−0.16486 (18)	0.30661 (15)	0.75262 (12)	0.0312 (3)
O3	−0.29370 (19)	−0.04558 (15)	1.21796 (13)	0.0342 (3)
O4	−0.1100 (2)	−0.09289 (17)	1.40071 (13)	0.0390 (4)
O5	0.4137 (2)	0.17360 (16)	1.34579 (14)	0.0388 (4)
O6	0.43555 (19)	0.36583 (17)	1.14336 (14)	0.0387 (4)
N3	−0.1603 (2)	−0.02278 (19)	1.27438 (16)	0.0299 (4)
N5	0.3597 (2)	0.2586 (2)	1.22071 (17)	0.0307 (4)
C11	−0.0001 (2)	0.2774 (2)	0.95610 (17)	0.0224 (4)
C12	−0.1032 (3)	0.1692 (2)	1.04196 (17)	0.0242 (4)
C13	−0.0523 (3)	0.0935 (2)	1.18455 (17)	0.0239 (4)
C14	0.0982 (3)	0.1206 (2)	1.24627 (18)	0.0264 (4)
C15	0.1973 (3)	0.2285 (2)	1.15786 (18)	0.0249 (4)
C16	0.1522 (2)	0.3077 (2)	1.01484 (18)	0.0252 (4)
C17	−0.0535 (3)	0.3612 (2)	0.79988 (18)	0.0254 (4)
N1	0.2797 (2)	0.52597 (18)	0.52280 (14)	0.0273 (4)
C2	0.4341 (3)	0.3538 (2)	0.54284 (18)	0.0288 (4)
C3	0.3871 (3)	0.6283 (2)	0.55097 (18)	0.0277 (4)
H12	−0.2074	0.1475	1.0031	0.029*
H14	0.1316	0.0677	1.3445	0.032*
H16	0.2237	0.3816	0.9575	0.030*
H1A	0.1735	0.5132	0.5818	0.033*
H1B	0.2168	0.5843	0.4327	0.033*
H2A	0.3590	0.2903	0.5210	0.035*
H2B	0.4948	0.2874	0.6414	0.035*
H3A	0.4460	0.5703	0.6498	0.033*
H3B	0.2813	0.7436	0.5338	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0371 (7)	0.0325 (8)	0.0231 (7)	−0.0156 (6)	0.0081 (5)	−0.0091 (6)
O2	0.0349 (7)	0.0377 (8)	0.0212 (7)	−0.0142 (6)	−0.0021 (5)	−0.0109 (6)
O3	0.0352 (7)	0.0376 (8)	0.0333 (8)	−0.0203 (6)	0.0052 (6)	−0.0124 (6)
O4	0.0462 (8)	0.0439 (8)	0.0195 (7)	−0.0196 (7)	0.0051 (6)	−0.0040 (6)
O5	0.0407 (8)	0.0472 (9)	0.0291 (8)	−0.0124 (7)	−0.0066 (6)	−0.0177 (7)
O6	0.0364 (8)	0.0461 (9)	0.0431 (9)	−0.0233 (7)	0.0044 (6)	−0.0206 (7)
N3	0.0324 (8)	0.0294 (9)	0.0250 (9)	−0.0111 (7)	0.0045 (7)	−0.0091 (7)
N5	0.0279 (8)	0.0353 (9)	0.0319 (10)	−0.0095 (7)	0.0001 (7)	−0.0179 (8)
C11	0.0234 (9)	0.0234 (9)	0.0190 (9)	−0.0068 (7)	0.0023 (7)	−0.0091 (8)
C12	0.0240 (9)	0.0257 (9)	0.0227 (10)	−0.0079 (7)	0.0009 (7)	−0.0106 (8)
C13	0.0269 (9)	0.0233 (9)	0.0203 (9)	−0.0097 (7)	0.0047 (7)	−0.0080 (8)
C14	0.0294 (9)	0.0261 (10)	0.0187 (10)	−0.0055 (8)	−0.0013 (7)	−0.0080 (8)
C15	0.0246 (9)	0.0267 (10)	0.0246 (10)	−0.0078 (7)	−0.0015 (7)	−0.0125 (8)
C16	0.0254 (9)	0.0233 (9)	0.0249 (10)	−0.0084 (7)	0.0039 (7)	−0.0089 (8)
C17	0.0238 (9)	0.0264 (10)	0.0211 (10)	−0.0059 (8)	0.0039 (7)	−0.0085 (8)
N1	0.0265 (8)	0.0396 (9)	0.0188 (8)	−0.0180 (7)	0.0024 (6)	−0.0100 (7)
C2	0.0343 (10)	0.0331 (11)	0.0221 (10)	−0.0191 (8)	0.0022 (8)	−0.0084 (8)
C3	0.0319 (9)	0.0331 (10)	0.0223 (10)	−0.0153 (8)	0.0013 (7)	−0.0124 (8)

Geometric parameters (Å, º)

O1—C17	1.256 (2)	C14—C15	1.378 (2)
O2—C17	1.2576 (18)	C14—H14	0.95
O3—N3	1.2287 (16)	C15—C16	1.380 (2)
O4—N3	1.2290 (18)	C16—H16	0.95
O5—N5	1.2249 (18)	N1—C2	1.484 (2)
O6—N5	1.2318 (19)	N1—C3	1.4917 (19)
N3—C13	1.472 (2)	N1—H1A	0.9200
N5—C15	1.473 (2)	N1—H1B	0.9200
C11—C12	1.389 (2)	C2—C3^i	1.511 (3)
C11—C16	1.392 (2)	C2—H2A	0.99
C11—C17	1.512 (2)	C2—H2B	0.99
C12—C13	1.382 (2)	C3—C2^i	1.511 (3)
C12—H12	0.95	C3—H3A	0.99
C13—C14	1.382 (2)	C3—H3B	0.99
O3—N3—O4	123.95 (15)	C11—C16—H16	120.6
O3—N3—C13	117.79 (14)	O1—C17—O2	126.12 (16)
O4—N3—C13	118.25 (13)	O1—C17—C11	117.11 (14)
O5—N5—O6	124.10 (14)	O2—C17—C11	116.77 (15)
O5—N5—C15	118.12 (15)	C2—N1—C3	111.54 (12)
O6—N5—C15	117.77 (15)	C2—N1—H1A	109.3
C12—C11—C16	119.61 (16)	C3—N1—H1A	109.3
C12—C11—C17	119.95 (14)	C2—N1—H1B	109.3
C16—C11—C17	120.43 (15)	C3—N1—H1B	109.3
C13—C12—C11	119.22 (14)	H1A—N1—H1B	108.0
C13—C12—H12	120.4	N1—C2—C3^i	110.23 (14)
C11—C12—H12	120.4	N1—C2—H2A	109.6
C14—C13—C12	122.67 (16)	C3^i—C2—H2A	109.6
C14—C13—N3	118.57 (15)	N1—C2—H2B	109.6
C12—C13—N3	118.76 (14)	C3^i—C2—H2B	109.6
C15—C14—C13	116.47 (16)	H2A—C2—H2B	108.1
C15—C14—H14	121.8	N1—C3—C2^i	109.77 (14)
C13—C14—H14	121.8	N1—C3—H3A	109.7
C14—C15—C16	123.24 (14)	C2^i—C3—H3A	109.7
C14—C15—N5	117.65 (15)	N1—C3—H3B	109.7
C16—C15—N5	119.11 (15)	C2^i—C3—H3B	109.7
C15—C16—C11	118.79 (16)	H3A—C3—H3B	108.2
C15—C16—H16	120.6
C16—C11—C12—C13	0.0 (2)	O6—N5—C15—C14	−174.07 (15)
C17—C11—C12—C13	179.90 (14)	O5—N5—C15—C16	−172.50 (15)
C11—C12—C13—C14	−0.1 (3)	O6—N5—C15—C16	6.2 (2)
C11—C12—C13—N3	−179.20 (15)	C14—C15—C16—C11	−0.3 (3)
O3—N3—C13—C14	179.99 (14)	N5—C15—C16—C11	179.42 (14)
O4—N3—C13—C14	−1.0 (2)	C12—C11—C16—C15	0.2 (2)
O3—N3—C13—C12	−0.8 (2)	C17—C11—C16—C15	−179.75 (15)
O4—N3—C13—C12	178.18 (15)	C12—C11—C17—O1	168.90 (15)
C12—C13—C14—C15	0.0 (3)	C16—C11—C17—O1	−11.2 (2)
N3—C13—C14—C15	179.11 (15)	C12—C11—C17—O2	−11.3 (2)
C13—C14—C15—C16	0.2 (3)	C16—C11—C17—O2	168.61 (15)
C13—C14—C15—N5	−179.49 (14)	C3—N1—C2—C3^i	−57.80 (19)
O5—N5—C15—C14	7.2 (2)	C2—N1—C3—C2^i	57.54 (19)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.92	1.80	2.695 (2)	165
N1—H1B···O2^ii	0.92	1.79	2.684 (2)	165
C2—H2A···O5^iii	0.99	2.45	3.191 (2)	131

Symmetry codes: (ii) −x, −y+1, −z+1; (iii) x, y, z−1.

(3) 3,5-Dinitrobenzoic acid–1,4-diazabicyclo[2.2.2]octane–water (2/1/0.13)

Crystal data

C6H13N2·C7H4N2O6·C7H3N2O6·0.13(H2O)	F(000) = 1117
Mr = 538.78	Dx = 1.597 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.6228 (4) Å	Cell parameters from 5110 reflections
b = 10.4320 (3) Å	θ = 2.7–27.5°
c = 19.6350 (6) Å	µ = 0.13 mm^−1
β = 109.6890 (18)°	T = 100 K
V = 2241.54 (12) Å^3	Plate, colourless
Z = 4	0.32 × 0.28 × 0.18 mm

Data collection

Kappa-CCD diffractometer	5110 independent reflections
Radiation source: fine-focus sealed X-ray tube	3867 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ϕ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→15
Tmin = 0.958, Tmax = 0.976	k = −13→0
5395 measured reflections	l = −25→23

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.045P)^2 + 0.6423P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
5110 reflections	Δρmax = 0.25 e Å^−3
348 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0039 (8)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O11	0.66392 (11)	0.38453 (11)	0.22752 (7)	0.0331 (3)
O12	0.52849 (10)	0.53637 (11)	0.17137 (6)	0.0271 (3)
O13	0.53074 (10)	0.69600 (12)	−0.05894 (6)	0.0312 (3)
O14	0.68797 (11)	0.66688 (12)	−0.09285 (6)	0.0333 (3)
O15	1.06525 (11)	0.52672 (13)	0.08661 (7)	0.0377 (3)
O16	1.05919 (11)	0.42542 (12)	0.18152 (7)	0.0357 (3)
N13	0.63439 (12)	0.65613 (13)	−0.04891 (7)	0.0244 (3)
N15	1.01033 (12)	0.48510 (13)	0.12531 (8)	0.0265 (3)
C11	0.69309 (14)	0.50001 (14)	0.13038 (8)	0.0213 (3)
C12	0.63362 (14)	0.56240 (14)	0.06536 (8)	0.0210 (3)
C13	0.69831 (14)	0.59090 (14)	0.01987 (8)	0.0206 (3)
C14	0.82110 (14)	0.56543 (14)	0.03716 (8)	0.0224 (3)
C15	0.87803 (14)	0.50748 (14)	0.10325 (9)	0.0221 (3)
C16	0.81676 (15)	0.47190 (15)	0.14976 (9)	0.0230 (3)
C17	0.62504 (15)	0.46801 (15)	0.18153 (9)	0.0237 (4)
O21	0.09559 (11)	0.38409 (13)	0.37194 (7)	0.0379 (3)
O22	0.25676 (10)	0.41831 (11)	0.47175 (6)	0.0280 (3)
O23	0.20600 (11)	0.36788 (13)	0.70696 (7)	0.0380 (3)
O24	0.02491 (12)	0.35095 (13)	0.71496 (7)	0.0384 (3)
O25	−0.31325 (11)	0.24332 (14)	0.50124 (8)	0.0434 (4)
O26	−0.29587 (11)	0.26685 (15)	0.39568 (7)	0.0470 (4)
N23	0.09474 (13)	0.35578 (13)	0.68003 (8)	0.0274 (3)
N25	−0.25376 (13)	0.26712 (14)	0.46165 (8)	0.0311 (3)
C21	0.06826 (14)	0.35806 (14)	0.48511 (9)	0.0209 (3)
C22	0.11717 (14)	0.36809 (14)	0.55994 (9)	0.0212 (3)
C23	0.04304 (15)	0.34455 (14)	0.60090 (9)	0.0222 (3)
C24	−0.07851 (14)	0.31132 (15)	0.57045 (9)	0.0238 (3)
C25	−0.12386 (14)	0.30102 (15)	0.49612 (9)	0.0237 (3)
C26	−0.05362 (14)	0.32399 (15)	0.45248 (9)	0.0230 (3)
C27	0.14540 (15)	0.38864 (15)	0.43804 (9)	0.0237 (3)
N1	0.43746 (11)	0.49658 (12)	0.26993 (7)	0.0202 (3)
N2	0.35090 (11)	0.46575 (12)	0.36995 (7)	0.0205 (3)
C1	0.40411 (16)	0.35973 (15)	0.27289 (9)	0.0273 (4)
C2	0.32762 (15)	0.57814 (16)	0.25599 (9)	0.0266 (4)
C3	0.53014 (15)	0.53304 (18)	0.33983 (9)	0.0286 (4)
C4	0.33426 (16)	0.34618 (15)	0.32615 (9)	0.0277 (4)
C5	0.28589 (16)	0.57361 (16)	0.32241 (9)	0.0269 (4)
C6	0.48355 (14)	0.49602 (17)	0.40182 (9)	0.0275 (4)
O1	0.88008 (14)	0.25647 (17)	0.28573 (9)	0.039 (4)*	0.131 (5)
H12	0.5498	0.5850	0.0525	0.025*
H14	0.8643	0.5866	0.0054	0.027*
H16	0.8584	0.4292	0.1940	0.028*
H22	0.2005	0.3908	0.5827	0.025*
H24	−0.1284	0.2963	0.5993	0.029*
H26	−0.0882	0.3166	0.4014	0.028*
H1	0.4796 (6)	0.5114 (2)	0.2217 (7)	0.024*
H2	0.3186	0.4541	0.4069	0.025*
H1A	0.4788	0.3063	0.2889	0.033*
H1B	0.3524	0.3304	0.2243	0.033*
H2A	0.2614	0.5466	0.2128	0.032*
H2B	0.3469	0.6675	0.2467	0.032*
H3A	0.5452	0.6265	0.3408	0.034*
H3B	0.6080	0.4883	0.3458	0.034*
H4A	0.2464	0.3320	0.2994	0.033*
H4B	0.3657	0.2717	0.3583	0.033*
H5A	0.3054	0.6557	0.3492	0.032*
H5B	0.1964	0.5601	0.3069	0.032*
H6A	0.5288	0.4205	0.4280	0.033*
H6B	0.4963	0.5679	0.4365	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0403 (7)	0.0332 (7)	0.0323 (7)	0.0041 (6)	0.0211 (6)	0.0098 (6)
O12	0.0279 (6)	0.0328 (6)	0.0275 (6)	0.0026 (5)	0.0184 (5)	0.0034 (5)
O13	0.0255 (6)	0.0347 (7)	0.0327 (7)	0.0014 (5)	0.0087 (5)	0.0056 (5)
O14	0.0344 (7)	0.0448 (7)	0.0238 (6)	−0.0070 (6)	0.0140 (5)	0.0041 (5)
O15	0.0269 (7)	0.0532 (8)	0.0391 (8)	−0.0014 (6)	0.0189 (6)	0.0038 (6)
O16	0.0293 (7)	0.0375 (7)	0.0383 (8)	0.0034 (5)	0.0087 (6)	0.0064 (6)
N13	0.0258 (8)	0.0263 (7)	0.0233 (7)	−0.0059 (6)	0.0110 (6)	−0.0005 (6)
N15	0.0250 (7)	0.0264 (7)	0.0299 (8)	−0.0006 (6)	0.0115 (6)	−0.0027 (6)
C11	0.0266 (8)	0.0183 (7)	0.0230 (8)	−0.0035 (6)	0.0135 (7)	−0.0043 (6)
C12	0.0232 (8)	0.0194 (7)	0.0236 (8)	−0.0026 (6)	0.0120 (7)	−0.0048 (6)
C13	0.0245 (8)	0.0199 (8)	0.0186 (8)	−0.0039 (6)	0.0088 (6)	−0.0017 (6)
C14	0.0263 (8)	0.0214 (8)	0.0242 (8)	−0.0048 (6)	0.0147 (7)	−0.0041 (6)
C15	0.0214 (8)	0.0206 (8)	0.0271 (9)	−0.0011 (6)	0.0117 (7)	−0.0035 (6)
C16	0.0293 (9)	0.0202 (8)	0.0214 (8)	−0.0006 (6)	0.0108 (7)	−0.0017 (6)
C17	0.0285 (9)	0.0245 (8)	0.0217 (8)	−0.0038 (7)	0.0131 (7)	−0.0017 (7)
O21	0.0338 (7)	0.0587 (8)	0.0257 (7)	−0.0073 (6)	0.0163 (6)	−0.0005 (6)
O22	0.0229 (6)	0.0355 (7)	0.0293 (6)	−0.0016 (5)	0.0139 (5)	0.0023 (5)
O23	0.0328 (7)	0.0486 (8)	0.0292 (7)	−0.0036 (6)	0.0058 (6)	−0.0031 (6)
O24	0.0448 (8)	0.0491 (8)	0.0291 (7)	0.0045 (6)	0.0226 (6)	0.0028 (6)
O25	0.0259 (7)	0.0591 (9)	0.0500 (8)	−0.0046 (6)	0.0191 (6)	0.0155 (7)
O26	0.0272 (7)	0.0737 (10)	0.0348 (8)	−0.0065 (7)	0.0037 (6)	0.0051 (7)
N23	0.0336 (8)	0.0242 (7)	0.0254 (7)	0.0025 (6)	0.0112 (7)	0.0006 (6)
N25	0.0219 (7)	0.0340 (8)	0.0375 (9)	0.0002 (6)	0.0101 (7)	0.0084 (7)
C21	0.0227 (8)	0.0178 (7)	0.0261 (8)	0.0029 (6)	0.0132 (7)	0.0028 (6)
C22	0.0199 (8)	0.0188 (7)	0.0269 (9)	0.0018 (6)	0.0105 (7)	0.0008 (6)
C23	0.0270 (8)	0.0195 (7)	0.0218 (8)	0.0040 (6)	0.0106 (7)	0.0017 (6)
C24	0.0242 (8)	0.0214 (8)	0.0312 (9)	0.0047 (7)	0.0164 (7)	0.0051 (7)
C25	0.0196 (8)	0.0211 (8)	0.0317 (9)	0.0023 (6)	0.0102 (7)	0.0049 (7)
C26	0.0252 (8)	0.0213 (8)	0.0246 (8)	0.0026 (6)	0.0112 (7)	0.0032 (6)
C27	0.0250 (9)	0.0237 (8)	0.0269 (9)	0.0028 (7)	0.0146 (7)	0.0022 (7)
N1	0.0208 (7)	0.0228 (7)	0.0208 (7)	−0.0017 (5)	0.0122 (6)	−0.0011 (5)
N2	0.0211 (7)	0.0244 (7)	0.0189 (7)	−0.0013 (5)	0.0105 (5)	−0.0004 (5)
C1	0.0373 (10)	0.0216 (8)	0.0293 (9)	−0.0038 (7)	0.0194 (8)	−0.0028 (7)
C2	0.0257 (9)	0.0310 (9)	0.0271 (9)	0.0048 (7)	0.0143 (7)	0.0082 (7)
C3	0.0223 (8)	0.0400 (10)	0.0259 (9)	−0.0074 (7)	0.0114 (7)	−0.0036 (7)
C4	0.0381 (10)	0.0223 (8)	0.0288 (9)	−0.0052 (7)	0.0192 (8)	−0.0015 (7)
C5	0.0280 (9)	0.0275 (8)	0.0298 (9)	0.0054 (7)	0.0157 (7)	0.0039 (7)
C6	0.0209 (8)	0.0403 (10)	0.0222 (9)	−0.0050 (7)	0.0083 (7)	−0.0015 (7)

Geometric parameters (Å, º)

O11—C17	1.2259 (19)	C22—H22	0.9500
O12—C17	1.2872 (19)	C23—C24	1.380 (2)
O13—N13	1.2260 (17)	C24—C25	1.379 (2)
O14—N13	1.2275 (16)	C24—H24	0.9500
O15—N15	1.2249 (18)	C25—C26	1.389 (2)
O16—N15	1.2271 (18)	C26—H26	0.9500
N13—C13	1.471 (2)	N1—C3	1.481 (2)
N15—C15	1.469 (2)	N1—C2	1.481 (2)
C11—C16	1.389 (2)	N1—C1	1.486 (2)
C11—C12	1.392 (2)	N1—H1	1.2139
C11—C17	1.510 (2)	N2—C6	1.489 (2)
C12—C13	1.380 (2)	N2—C4	1.490 (2)
C12—H12	0.9500	N2—C5	1.494 (2)
C13—C14	1.377 (2)	N2—H2	0.9300
C14—C15	1.382 (2)	C1—C4	1.531 (2)
C14—H14	0.9500	C1—H1A	0.9900
C15—C16	1.385 (2)	C1—H1B	0.9900
C16—H16	0.9500	C2—C5	1.538 (2)
O21—C27	1.2312 (19)	C2—H2A	0.9900
O22—C27	1.2774 (19)	C2—H2B	0.9900
O23—N23	1.2276 (18)	C3—C6	1.539 (2)
O24—N23	1.2275 (18)	C3—H3A	0.9900
O25—N25	1.2272 (18)	C3—H3B	0.9900
O26—N25	1.2208 (18)	C4—H4A	0.9900
N23—C23	1.470 (2)	C4—H4B	0.9900
N25—C25	1.475 (2)	C5—H5A	0.9900
C21—C22	1.389 (2)	C5—H5B	0.9900
C21—C26	1.390 (2)	C6—H6A	0.9900
C21—C27	1.522 (2)	C6—H6B	0.9900
C22—C23	1.384 (2)
O13—N13—O14	124.05 (14)	O21—C27—O22	126.15 (15)
O13—N13—C13	118.00 (13)	O21—C27—C21	117.90 (14)
O14—N13—C13	117.95 (13)	O22—C27—C21	115.94 (14)
O15—N15—O16	123.91 (14)	C3—N1—C2	109.65 (12)
O15—N15—C15	118.25 (14)	C3—N1—C1	109.18 (13)
O16—N15—C15	117.85 (14)	C2—N1—C1	109.84 (12)
C16—C11—C12	119.90 (14)	C3—N1—H1	109.4
C16—C11—C17	119.78 (14)	C2—N1—H1	109.4
C12—C11—C17	120.26 (14)	C1—N1—H1	109.4
C13—C12—C11	118.96 (15)	C6—N2—C4	109.55 (12)
C13—C12—H12	120.5	C6—N2—C5	109.68 (12)
C11—C12—H12	120.5	C4—N2—C5	109.25 (12)
C14—C13—C12	122.97 (15)	C6—N2—H2	109.4
C14—C13—N13	118.47 (13)	C4—N2—H2	109.4
C12—C13—N13	118.51 (14)	C5—N2—H2	109.4
C13—C14—C15	116.41 (14)	N1—C1—C4	108.71 (13)
C13—C14—H14	121.8	N1—C1—H1A	109.9
C15—C14—H14	121.8	C4—C1—H1A	109.9
C14—C15—C16	123.15 (15)	N1—C1—H1B	109.9
C14—C15—N15	117.97 (14)	C4—C1—H1B	109.9
C16—C15—N15	118.87 (15)	H1A—C1—H1B	108.3
C15—C16—C11	118.52 (15)	N1—C2—C5	108.92 (13)
C15—C16—H16	120.7	N1—C2—H2A	109.9
C11—C16—H16	120.7	C5—C2—H2A	109.9
O11—C17—O12	126.41 (15)	N1—C2—H2B	109.9
O11—C17—C11	120.08 (15)	C5—C2—H2B	109.9
O12—C17—C11	113.51 (14)	H2A—C2—H2B	108.3
O23—N23—O24	124.22 (15)	N1—C3—C6	109.19 (12)
O23—N23—C23	117.37 (14)	N1—C3—H3A	109.8
O24—N23—C23	118.40 (14)	C6—C3—H3A	109.8
O26—N25—O25	124.17 (15)	N1—C3—H3B	109.8
O26—N25—C25	118.04 (14)	C6—C3—H3B	109.8
O25—N25—C25	117.78 (15)	H3A—C3—H3B	108.3
C22—C21—C26	119.80 (14)	N2—C4—C1	108.74 (13)
C22—C21—C27	120.75 (14)	N2—C4—H4A	109.9
C26—C21—C27	119.41 (14)	C1—C4—H4A	109.9
C23—C22—C21	119.22 (15)	N2—C4—H4B	109.9
C23—C22—H22	120.4	C1—C4—H4B	109.9
C21—C22—H22	120.4	H4A—C4—H4B	108.3
C24—C23—C22	122.65 (15)	N2—C5—C2	108.38 (12)
C24—C23—N23	118.19 (14)	N2—C5—H5A	110.0
C22—C23—N23	119.16 (14)	C2—C5—H5A	110.0
C25—C24—C23	116.66 (15)	N2—C5—H5B	110.0
C25—C24—H24	121.7	C2—C5—H5B	110.0
C23—C24—H24	121.7	H5A—C5—H5B	108.4
C24—C25—C26	123.02 (15)	N2—C6—C3	108.13 (13)
C24—C25—N25	118.15 (14)	N2—C6—H6A	110.1
C26—C25—N25	118.81 (15)	C3—C6—H6A	110.1
C25—C26—C21	118.65 (15)	N2—C6—H6B	110.1
C25—C26—H26	120.7	C3—C6—H6B	110.1
C21—C26—H26	120.7	H6A—C6—H6B	108.4
C16—C11—C12—C13	2.5 (2)	C22—C23—C24—C25	0.6 (2)
C17—C11—C12—C13	179.71 (14)	N23—C23—C24—C25	−179.69 (13)
C11—C12—C13—C14	−2.9 (2)	C23—C24—C25—C26	−0.9 (2)
C11—C12—C13—N13	179.63 (13)	C23—C24—C25—N25	−179.31 (13)
O13—N13—C13—C14	−169.00 (14)	O26—N25—C25—C24	174.95 (15)
O14—N13—C13—C14	11.3 (2)	O25—N25—C25—C24	−3.7 (2)
O13—N13—C13—C12	8.6 (2)	O26—N25—C25—C26	−3.6 (2)
O14—N13—C13—C12	−171.17 (14)	O25—N25—C25—C26	177.79 (15)
C12—C13—C14—C15	0.7 (2)	C24—C25—C26—C21	0.5 (2)
N13—C13—C14—C15	178.14 (13)	N25—C25—C26—C21	178.92 (14)
C13—C14—C15—C16	2.1 (2)	C22—C21—C26—C25	0.2 (2)
C13—C14—C15—N15	−176.77 (13)	C27—C21—C26—C25	−177.65 (14)
O15—N15—C15—C14	5.0 (2)	C22—C21—C27—O21	−176.56 (15)
O16—N15—C15—C14	−174.86 (14)	C26—C21—C27—O21	1.2 (2)
O15—N15—C15—C16	−173.89 (14)	C22—C21—C27—O22	2.7 (2)
O16—N15—C15—C16	6.2 (2)	C26—C21—C27—O22	−179.53 (14)
C14—C15—C16—C11	−2.5 (2)	C3—N1—C1—C4	68.55 (17)
N15—C15—C16—C11	176.37 (13)	C2—N1—C1—C4	−51.72 (17)
C12—C11—C16—C15	0.1 (2)	C3—N1—C2—C5	−52.01 (17)
C17—C11—C16—C15	−177.15 (14)	C1—N1—C2—C5	67.97 (16)
C16—C11—C17—O11	−23.0 (2)	C2—N1—C3—C6	68.13 (17)
C12—C11—C17—O11	159.75 (15)	C1—N1—C3—C6	−52.25 (17)
C16—C11—C17—O12	156.38 (14)	C6—N2—C4—C1	−51.78 (17)
C12—C11—C17—O12	−20.9 (2)	C5—N2—C4—C1	68.39 (17)
C26—C21—C22—C23	−0.4 (2)	N1—C1—C4—N2	−14.16 (19)
C27—C21—C22—C23	177.42 (14)	C6—N2—C5—C2	68.04 (16)
C21—C22—C23—C24	−0.1 (2)	C4—N2—C5—C2	−52.05 (17)
C21—C22—C23—N23	−179.71 (13)	N1—C2—C5—N2	−13.41 (18)
O23—N23—C23—C24	170.22 (14)	C4—N2—C6—C3	67.78 (16)
O24—N23—C23—C24	−8.9 (2)	C5—N2—C6—C3	−52.13 (17)
O23—N23—C23—C22	−10.1 (2)	N1—C3—C6—N2	−13.43 (18)
O24—N23—C23—C22	170.78 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O12	1.21 (2)	1.32 (2)	2.533 (2)	176 (1)
N2—H2···O22	0.93	1.70	2.629 (2)	175
C1—H1B···O14^i	0.99	2.46	3.342 (2)	148
C2—H2B···O11^ii	0.99	2.33	3.211 (2)	147
C6—H6B···O13^iii	0.99	2.49	3.306 (2)	139
C26—H26···O1^iv	0.95	2.26	3.180 (2)	162
O1···O11			2.733 (2)
O1···O21^v			2.838 (2)
O1···O24^vi			2.756 (2)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y+3/2, z+1/2; (iv) x−1, y, z; (v) x+1, y, z; (vi) x+1, −y+1/2, z−1/2.

(4) 3,5-Dinitrobenzoic acid–N,N,N',N'-tetramethylethylenediamine (2/1)

Crystal data

2(C7H3N2O6)·C6H18N2	F(000) = 564
Mr = 540.45	Dx = 1.495 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.0665 (2) Å	Cell parameters from 4055 reflections
b = 9.0635 (3) Å	θ = 2.9–32.1°
c = 21.8452 (6) Å	µ = 0.13 mm^−1
β = 92.031 (2)°	T = 100 K
V = 1200.38 (7) Å^3	Block, colourless
Z = 2	0.35 × 0.28 × 0.24 mm

Data collection

Kappa-CCD diffractometer	4055 independent reflections
Radiation source: fine-focus sealed X-ray tube	3109 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ϕ scans and ω scans with κ offsets	θmax = 32.1°, θmin = 2.9°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→9
Tmin = 0.957, Tmax = 0.971	k = 0→13
4055 measured reflections	l = −32→32

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.165	w = 1/[σ^2(Fo^2) + (0.0598P)^2 + 0.6243P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
4055 reflections	Δρmax = 0.39 e Å^−3
175 parameters	Δρmin = −0.35 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (8)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
C1	0.4248 (2)	0.56775 (16)	0.49883 (7)	0.0251 (3)
N2	0.53995 (19)	0.69807 (14)	0.52707 (5)	0.0238 (3)
C3	0.7120 (3)	0.75859 (18)	0.48694 (7)	0.0310 (3)
C4	0.3758 (3)	0.81410 (18)	0.54166 (8)	0.0320 (3)
O1	0.98581 (19)	0.55026 (16)	0.57655 (5)	0.0361 (3)
O2	0.71388 (17)	0.62434 (13)	0.63570 (5)	0.0289 (3)
O3	0.8220 (3)	0.58143 (19)	0.85735 (6)	0.0549 (4)
O4	1.1290 (3)	0.49912 (19)	0.89778 (6)	0.0583 (5)
O5	1.6636 (2)	0.28016 (16)	0.76694 (7)	0.0442 (3)
O6	1.6070 (2)	0.28000 (15)	0.66830 (6)	0.0392 (3)
N3	1.0066 (3)	0.52831 (18)	0.85339 (6)	0.0390 (4)
N5	1.5548 (2)	0.31231 (15)	0.72034 (7)	0.0314 (3)
C11	1.0317 (2)	0.51612 (16)	0.68339 (6)	0.0226 (3)
C12	0.9577 (2)	0.54362 (17)	0.74161 (6)	0.0250 (3)
C13	1.0854 (3)	0.49720 (17)	0.79201 (6)	0.0274 (3)
C14	1.2826 (3)	0.42282 (17)	0.78700 (7)	0.0283 (3)
C15	1.3486 (2)	0.39549 (16)	0.72811 (7)	0.0252 (3)
C16	1.2296 (2)	0.44124 (16)	0.67644 (7)	0.0242 (3)
C17	0.9013 (2)	0.56779 (16)	0.62700 (6)	0.0243 (3)
H1A	0.3817	0.5902	0.4557	0.030*
H1B	0.2890	0.5467	0.5211	0.030*
H2	0.6090	0.6677	0.5636	0.029*
H3A	0.6425	0.7927	0.4483	0.046*
H3B	0.8198	0.6813	0.4785	0.046*
H3C	0.7869	0.8415	0.5076	0.046*
H4A	0.4520	0.8984	0.5609	0.048*
H4B	0.2689	0.7738	0.5698	0.048*
H4C	0.2986	0.8464	0.5038	0.048*
H12	0.8219	0.5934	0.7469	0.030*
H14	1.3681	0.3922	0.8220	0.034*
H16	1.2821	0.4219	0.6368	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0223 (6)	0.0257 (7)	0.0273 (7)	−0.0007 (5)	−0.0007 (5)	−0.0020 (5)
N2	0.0238 (5)	0.0249 (6)	0.0225 (5)	0.0007 (4)	0.0007 (4)	0.0000 (4)
C3	0.0329 (8)	0.0322 (7)	0.0281 (7)	−0.0063 (6)	0.0043 (6)	0.0024 (6)
C4	0.0324 (8)	0.0278 (7)	0.0358 (8)	0.0060 (6)	0.0011 (6)	−0.0034 (6)
O1	0.0274 (5)	0.0590 (8)	0.0221 (5)	0.0052 (5)	0.0020 (4)	0.0008 (5)
O2	0.0263 (5)	0.0356 (6)	0.0245 (5)	0.0077 (4)	−0.0009 (4)	−0.0010 (4)
O3	0.0679 (10)	0.0664 (10)	0.0316 (7)	0.0271 (8)	0.0177 (6)	0.0010 (6)
O4	0.0852 (12)	0.0680 (10)	0.0213 (6)	0.0233 (9)	−0.0036 (6)	0.0057 (6)
O5	0.0331 (6)	0.0478 (8)	0.0513 (8)	0.0096 (5)	−0.0069 (6)	0.0126 (6)
O6	0.0320 (6)	0.0393 (7)	0.0469 (7)	0.0082 (5)	0.0081 (5)	−0.0008 (6)
N3	0.0569 (9)	0.0379 (8)	0.0224 (6)	0.0115 (7)	0.0052 (6)	0.0025 (6)
N5	0.0235 (6)	0.0267 (6)	0.0438 (8)	0.0011 (5)	−0.0001 (5)	0.0058 (6)
C11	0.0206 (6)	0.0256 (6)	0.0215 (6)	−0.0014 (5)	0.0009 (5)	−0.0008 (5)
C12	0.0248 (6)	0.0272 (6)	0.0231 (6)	0.0015 (5)	0.0026 (5)	0.0007 (5)
C13	0.0340 (7)	0.0290 (7)	0.0194 (6)	0.0021 (6)	0.0032 (5)	0.0020 (5)
C14	0.0309 (7)	0.0278 (7)	0.0259 (7)	0.0003 (6)	−0.0040 (5)	0.0054 (5)
C15	0.0207 (6)	0.0237 (6)	0.0311 (7)	0.0009 (5)	0.0002 (5)	0.0021 (5)
C16	0.0218 (6)	0.0257 (6)	0.0251 (6)	−0.0008 (5)	0.0028 (5)	−0.0015 (5)
C17	0.0217 (6)	0.0289 (7)	0.0223 (6)	−0.0010 (5)	−0.0008 (5)	−0.0007 (5)

Geometric parameters (Å, º)

C1—N2	1.4943 (19)	O4—N3	1.229 (2)
C1—C1^i	1.529 (3)	O5—N5	1.2283 (19)
C1—H1A	0.9900	O6—N5	1.226 (2)
C1—H1B	0.9900	N3—C13	1.467 (2)
N2—C3	1.4914 (19)	N5—C15	1.4754 (19)
N2—C4	1.4905 (19)	C11—C12	1.3864 (19)
N2—H2	0.9300	C11—C16	1.3922 (19)
C3—H3A	0.9800	C11—C17	1.5144 (19)
C3—H3B	0.9800	C12—C13	1.389 (2)
C3—H3C	0.9800	C12—H12	0.9500
C4—H4A	0.9800	C13—C14	1.381 (2)
C4—H4B	0.9800	C14—C15	1.383 (2)
C4—H4C	0.9800	C14—H14	0.9500
O1—C17	1.2422 (18)	C15—C16	1.382 (2)
O2—C17	1.2676 (18)	C16—H16	0.9500
O3—N3	1.225 (2)
N2—C1—C1^i	110.58 (14)	O4—N3—C13	118.20 (16)
N2—C1—H1A	109.5	O6—N5—O5	124.25 (14)
C1^i—C1—H1A	109.5	O6—N5—C15	118.45 (13)
N2—C1—H1B	109.5	O5—N5—C15	117.30 (14)
C1^i—C1—H1B	109.5	C12—C11—C16	119.75 (13)
H1A—C1—H1B	108.1	C12—C11—C17	120.91 (12)
C4—N2—C3	110.68 (12)	C16—C11—C17	119.33 (12)
C4—N2—C1	109.88 (11)	C11—C12—C13	118.90 (13)
C3—N2—C1	112.00 (11)	C11—C12—H12	120.6
C4—N2—H2	108.1	C13—C12—H12	120.6
C3—N2—H2	108.1	C14—C13—C12	123.05 (14)
C1—N2—H2	108.1	C14—C13—N3	118.52 (14)
N2—C3—H3A	109.5	C12—C13—N3	118.43 (14)
N2—C3—H3B	109.5	C13—C14—C15	116.19 (13)
H3A—C3—H3B	109.5	C13—C14—H14	121.9
N2—C3—H3C	109.5	C15—C14—H14	121.9
H3A—C3—H3C	109.5	C16—C15—C14	123.09 (13)
H3B—C3—H3C	109.5	C16—C15—N5	118.68 (13)
N2—C4—H4A	109.5	C14—C15—N5	118.23 (13)
N2—C4—H4B	109.5	C15—C16—C11	119.01 (13)
H4A—C4—H4B	109.5	C15—C16—H16	120.5
N2—C4—H4C	109.5	C11—C16—H16	120.5
H4A—C4—H4C	109.5	O1—C17—O2	125.82 (14)
H4B—C4—H4C	109.5	O1—C17—C11	117.51 (13)
O3—N3—O4	123.86 (15)	O2—C17—C11	116.66 (12)
O3—N3—C13	117.93 (14)
C1^i—C1—N2—C4	−163.00 (15)	C13—C14—C15—N5	−178.14 (13)
C1^i—C1—N2—C3	73.56 (18)	O6—N5—C15—C16	−3.8 (2)
C16—C11—C12—C13	0.9 (2)	O5—N5—C15—C16	176.04 (14)
C17—C11—C12—C13	−178.50 (13)	O6—N5—C15—C14	175.61 (14)
C11—C12—C13—C14	−0.8 (2)	O5—N5—C15—C14	−4.5 (2)
C11—C12—C13—N3	179.34 (14)	C14—C15—C16—C11	−1.2 (2)
O3—N3—C13—C14	−173.10 (17)	N5—C15—C16—C11	178.19 (13)
O4—N3—C13—C14	6.6 (3)	C12—C11—C16—C15	0.1 (2)
O3—N3—C13—C12	6.8 (3)	C17—C11—C16—C15	179.48 (13)
O4—N3—C13—C12	−173.53 (17)	C12—C11—C17—O1	174.20 (14)
C12—C13—C14—C15	−0.2 (2)	C16—C11—C17—O1	−5.2 (2)
N3—C13—C14—C15	179.61 (14)	C12—C11—C17—O2	−6.3 (2)
C13—C14—C15—C16	1.3 (2)	C16—C11—C17—O2	174.30 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.93	1.72	2.648 (2)	173
C1—H1B···O1^ii	0.99	2.24	3.213 (2)	168

Symmetry code: (ii) x−1, y, z.

(5) 3,5-Dinitrobenzoic acid–N,N'-dimethylpiperazine (2/1)

Crystal data

2(C7H3N2O6)·C6H16N2	F(000) = 560
Mr = 538.44	Dx = 1.531 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.1399 (2) Å	Cell parameters from 3926 reflections
b = 21.1749 (6) Å	θ = 2.8–32.0°
c = 7.8255 (2) Å	µ = 0.13 mm^−1
β = 99.1990 (18)°	T = 100 K
V = 1167.90 (6) Å^3	Block, colourless
Z = 2	0.37 × 0.35 × 0.30 mm

Data collection

Kappa-CCD diffractometer	3926 independent reflections
Radiation source: fine-focus sealed X-ray tube	3018 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ϕ scans and ω scans with κ offsets	θmax = 32.0°, θmin = 2.8°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→10
Tmin = 0.954, Tmax = 0.962	k = 0→31
4083 measured reflections	l = −11→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.0418P)^2 + 0.4394P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
3926 reflections	Δρmax = 0.31 e Å^−3
174 parameters	Δρmin = −0.30 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.035 (6)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
N1	0.65628 (14)	0.50151 (5)	0.64295 (13)	0.0214 (2)
C2	0.66315 (17)	0.53732 (6)	0.48011 (16)	0.0235 (2)
C3	0.45564 (17)	0.49525 (6)	0.67237 (16)	0.0234 (2)
C4	0.77689 (19)	0.53197 (6)	0.79286 (17)	0.0285 (3)
O1	0.74472 (14)	0.38301 (4)	0.62272 (13)	0.0301 (2)
O2	0.91752 (14)	0.40255 (4)	0.41281 (14)	0.0318 (2)
O3	1.35007 (15)	0.22711 (5)	0.31124 (16)	0.0402 (3)
O4	1.25003 (16)	0.13096 (5)	0.32530 (16)	0.0421 (3)
O5	0.66526 (16)	0.08875 (4)	0.53203 (14)	0.0350 (2)
O6	0.53686 (15)	0.16206 (5)	0.66795 (14)	0.0335 (2)
N3	1.23636 (16)	0.18805 (6)	0.34787 (15)	0.0290 (2)
N5	0.65460 (16)	0.14342 (5)	0.58113 (14)	0.0261 (2)
C11	0.88408 (16)	0.29673 (5)	0.50005 (15)	0.0212 (2)
C12	1.04258 (17)	0.27550 (6)	0.43384 (15)	0.0228 (2)
C13	1.07121 (17)	0.21101 (6)	0.42103 (15)	0.0232 (2)
C14	0.94623 (17)	0.16652 (6)	0.46723 (16)	0.0240 (2)
C15	0.79075 (17)	0.18945 (5)	0.53267 (15)	0.0221 (2)
C16	0.75733 (17)	0.25331 (6)	0.55295 (15)	0.0221 (2)
C17	0.84750 (17)	0.36713 (6)	0.51177 (16)	0.0235 (2)
H1	0.7036	0.4612	0.6298	0.026*
H2A	0.7962	0.5404	0.4598	0.028*
H2B	0.6148	0.5807	0.4916	0.028*
H3A	0.4026	0.5376	0.6883	0.028*
H3B	0.4516	0.4705	0.7790	0.028*
H4A	0.9066	0.5364	0.7683	0.043*
H4B	0.7779	0.5058	0.8963	0.043*
H4C	0.7256	0.5738	0.8128	0.043*
H12	1.1296	0.3047	0.3980	0.027*
H14	0.9663	0.1225	0.4546	0.029*
H16	0.6509	0.2672	0.6016	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0217 (4)	0.0188 (4)	0.0238 (5)	0.0000 (3)	0.0036 (4)	−0.0003 (4)
C2	0.0228 (5)	0.0219 (5)	0.0263 (6)	−0.0030 (4)	0.0051 (4)	0.0025 (5)
C3	0.0228 (5)	0.0247 (5)	0.0237 (6)	−0.0006 (4)	0.0070 (4)	0.0007 (5)
C4	0.0293 (6)	0.0279 (6)	0.0271 (6)	−0.0055 (5)	0.0011 (5)	−0.0025 (5)
O1	0.0389 (5)	0.0216 (4)	0.0311 (5)	0.0058 (4)	0.0099 (4)	0.0009 (4)
O2	0.0294 (5)	0.0226 (4)	0.0448 (6)	−0.0022 (4)	0.0106 (4)	0.0060 (4)
O3	0.0292 (5)	0.0447 (6)	0.0493 (7)	0.0026 (4)	0.0143 (5)	0.0019 (5)
O4	0.0381 (6)	0.0347 (6)	0.0547 (7)	0.0105 (4)	0.0112 (5)	−0.0096 (5)
O5	0.0522 (6)	0.0202 (4)	0.0340 (5)	−0.0075 (4)	0.0112 (5)	−0.0029 (4)
O6	0.0352 (5)	0.0295 (5)	0.0387 (6)	−0.0038 (4)	0.0146 (4)	−0.0004 (4)
N3	0.0252 (5)	0.0320 (6)	0.0294 (6)	0.0060 (4)	0.0027 (4)	−0.0026 (5)
N5	0.0321 (6)	0.0219 (5)	0.0239 (5)	−0.0039 (4)	0.0034 (4)	0.0004 (4)
C11	0.0224 (5)	0.0199 (5)	0.0202 (5)	−0.0005 (4)	0.0007 (4)	−0.0005 (4)
C12	0.0216 (5)	0.0240 (5)	0.0221 (5)	−0.0008 (4)	0.0012 (4)	0.0012 (4)
C13	0.0215 (5)	0.0259 (6)	0.0217 (5)	0.0037 (4)	0.0015 (4)	−0.0010 (5)
C14	0.0275 (6)	0.0205 (5)	0.0227 (6)	0.0022 (4)	0.0003 (4)	−0.0004 (4)
C15	0.0260 (6)	0.0200 (5)	0.0195 (5)	−0.0025 (4)	0.0012 (4)	0.0008 (4)
C16	0.0230 (5)	0.0218 (5)	0.0211 (5)	0.0006 (4)	0.0025 (4)	−0.0002 (4)
C17	0.0208 (5)	0.0205 (5)	0.0276 (6)	−0.0001 (4)	−0.0008 (4)	0.0005 (4)

Geometric parameters (Å, º)

N1—C4	1.4869 (16)	O4—N3	1.2279 (16)
N1—C2	1.4904 (16)	O5—N5	1.2260 (14)
N1—C3	1.4927 (15)	O6—N5	1.2275 (15)
N1—H1	0.9300	N3—C13	1.4732 (16)
C2—C3^i	1.5151 (17)	N5—C15	1.4686 (16)
C2—H2A	0.9900	C11—C12	1.3924 (17)
C2—H2B	0.9900	C11—C16	1.3984 (17)
C3—C2^i	1.5151 (17)	C11—C17	1.5186 (17)
C3—H3A	0.9900	C12—C13	1.3869 (17)
C3—H3B	0.9900	C12—H12	0.9500
C4—H4A	0.9800	C13—C14	1.3848 (18)
C4—H4B	0.9800	C14—C15	1.3828 (18)
C4—H4C	0.9800	C14—H14	0.9500
O1—C17	1.2685 (16)	C15—C16	1.3866 (17)
O2—C17	1.2393 (16)	C16—H16	0.9500
O3—N3	1.2247 (16)
C2—N1—C3	109.92 (9)	O4—N3—C13	117.88 (12)
C2—N1—C4	111.09 (9)	O5—N5—O6	124.02 (11)
C3—N1—C4	111.46 (10)	O5—N5—C15	117.97 (11)
C4—N1—H1	108.1	O6—N5—C15	118.02 (10)
C2—N1—H1	108.1	C12—C11—C16	120.05 (11)
C3—N1—H1	108.1	C12—C11—C17	119.82 (11)
N1—C2—C3^i	110.55 (9)	C16—C11—C17	120.12 (11)
N1—C2—H2A	109.5	C13—C12—C11	118.87 (11)
C3^i—C2—H2A	109.5	C13—C12—H12	120.6
N1—C2—H2B	109.5	C11—C12—H12	120.6
C3^i—C2—H2B	109.5	C14—C13—C12	122.85 (11)
H2A—C2—H2B	108.1	C14—C13—N3	117.79 (11)
N1—C3—C2^i	110.43 (10)	C12—C13—N3	119.30 (11)
N1—C3—H3A	109.6	C15—C14—C13	116.54 (11)
C2^i—C3—H3A	109.6	C15—C14—H14	121.7
N1—C3—H3B	109.6	C13—C14—H14	121.7
C2^i—C3—H3B	109.6	C14—C15—C16	123.22 (11)
H3A—C3—H3B	108.1	C14—C15—N5	117.79 (11)
N1—C4—H4A	109.5	C16—C15—N5	118.98 (11)
N1—C4—H4B	109.5	C15—C16—C11	118.42 (11)
H4A—C4—H4B	109.5	C15—C16—H16	120.8
N1—C4—H4C	109.5	C11—C16—H16	120.8
H4A—C4—H4C	109.5	O2—C17—O1	127.05 (12)
H4B—C4—H4C	109.5	O2—C17—C11	117.77 (11)
O3—N3—O4	124.08 (12)	O1—C17—C11	115.18 (11)
O3—N3—C13	118.03 (11)
C4—N1—C2—C3^i	178.33 (10)	C13—C14—C15—C16	−0.07 (18)
C3—N1—C2—C3^i	−57.83 (13)	C13—C14—C15—N5	179.38 (10)
C4—N1—C3—C2^i	−178.61 (10)	O5—N5—C15—C14	−13.38 (17)
C2—N1—C3—C2^i	57.77 (13)	O6—N5—C15—C14	166.77 (11)
C16—C11—C12—C13	0.25 (17)	O5—N5—C15—C16	166.09 (11)
C17—C11—C12—C13	−178.71 (11)	O6—N5—C15—C16	−13.75 (17)
C11—C12—C13—C14	1.69 (18)	C14—C15—C16—C11	1.90 (18)
C11—C12—C13—N3	178.77 (10)	N5—C15—C16—C11	−177.54 (10)
O3—N3—C13—C14	−178.03 (12)	C12—C11—C16—C15	−1.96 (17)
O4—N3—C13—C14	2.91 (17)	C17—C11—C16—C15	177.00 (10)
O3—N3—C13—C12	4.74 (17)	C12—C11—C17—O2	23.92 (16)
O4—N3—C13—C12	−174.32 (12)	C16—C11—C17—O2	−155.04 (12)
C12—C13—C14—C15	−1.76 (18)	C12—C11—C17—O1	−156.91 (11)
N3—C13—C14—C15	−178.89 (10)	C16—C11—C17—O1	24.13 (16)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.93	1.68	2.599 (2)	167
C2—H2A···O2^ii	0.99	2.45	3.238 (2)	137
C4—H4A···O2^ii	0.98	2.41	3.224 (2)	140
C4—H4B···O5^iii	0.98	2.46	3.339 (2)	149

Symmetry codes: (ii) −x+2, −y+1, −z+1; (iii) x, −y+1/2, z+1/2.

(6) 3,5-Dinitrobenzoic acid–1,2-bis(4'-pyridyl)ethane (2/1)

Crystal data

C12H13N2·C14H7N4O12	F(000) = 628
Mr = 608.48	Dx = 1.566 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.1344 (6) Å	Cell parameters from 13358 reflections
b = 4.9420 (2) Å	θ = 3.1–27.5°
c = 27.5984 (14) Å	µ = 0.13 mm^−1
β = 110.960 (2)°	T = 150 K
V = 1290.78 (11) Å^3	Block, colourless
Z = 2	0.32 × 0.25 × 0.20 mm

Data collection

Kappa-CCD diffractometer	2838 independent reflections
Radiation source: fine-focus sealed X-ray tube	2287 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ϕ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→13
Tmin = 0.961, Tmax = 0.975	k = −6→0
13358 measured reflections	l = −35→32

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0414P)^2 + 0.4399P] where P = (Fo^2 + 2Fc^2)/3
2838 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.01701 (11)	1.4685 (2)	0.63186 (4)	0.0312 (3)
O2	1.13472 (13)	1.4960 (2)	0.57700 (5)	0.0385 (3)
O3	1.49811 (13)	2.1870 (3)	0.60855 (5)	0.0407 (3)
O4	1.54102 (13)	2.4678 (3)	0.67249 (5)	0.0414 (3)
O5	1.26655 (14)	2.4347 (2)	0.78189 (5)	0.0394 (3)
O6	1.11876 (14)	2.1072 (3)	0.77488 (5)	0.0449 (3)
N3	1.47954 (13)	2.2714 (3)	0.64726 (5)	0.0301 (3)
N5	1.20649 (14)	2.2254 (3)	0.76167 (5)	0.0306 (3)
C11	1.19287 (15)	1.8005 (3)	0.64793 (6)	0.0237 (3)
C12	1.29817 (15)	1.9215 (3)	0.63416 (6)	0.0249 (3)
C13	1.37361 (15)	2.1346 (3)	0.66373 (6)	0.0249 (3)
C14	1.34857 (15)	2.2342 (3)	0.70634 (6)	0.0260 (3)
C15	1.24212 (15)	2.1109 (3)	0.71870 (6)	0.0244 (3)
C16	1.16395 (15)	1.8958 (3)	0.69066 (6)	0.0242 (3)
C17	1.10939 (15)	1.5691 (3)	0.61511 (6)	0.0257 (3)
N1	0.86651 (13)	1.0833 (3)	0.58171 (5)	0.0259 (3)
C2	0.79013 (16)	0.9620 (3)	0.60625 (6)	0.0274 (3)
C3	0.69732 (16)	0.7560 (3)	0.58328 (6)	0.0270 (3)
C4	0.68152 (14)	0.6701 (3)	0.53351 (6)	0.0237 (3)
C5	0.76474 (15)	0.7954 (3)	0.50919 (6)	0.0277 (3)
C6	0.85513 (16)	1.0022 (3)	0.53415 (6)	0.0290 (4)
C7	0.57701 (15)	0.4516 (3)	0.50692 (6)	0.0268 (3)
H1	0.9733	1.3433	0.6120	0.047*	0.50
H12	1.3180	1.8590	0.6049	0.030*
H14	1.4018	2.3804	0.7262	0.031*
H116	1.0920	1.8147	0.7003	0.029*
H1A	0.9242	1.2164	0.5969	0.031*	0.50
H2	0.8002	1.0193	0.6402	0.033*
H3	0.6442	0.6726	0.6014	0.032*
H5	0.7592	0.7387	0.4756	0.033*
H6	0.9104	1.0887	0.5172	0.035*
H7A	0.5936	0.2919	0.5300	0.032*
H7B	0.5920	0.3956	0.4748	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0240 (6)	0.0318 (7)	0.0376 (7)	−0.0070 (5)	0.0108 (5)	−0.0070 (5)
O2	0.0375 (7)	0.0441 (8)	0.0367 (7)	−0.0069 (5)	0.0169 (6)	−0.0143 (5)
O3	0.0359 (7)	0.0521 (8)	0.0423 (7)	−0.0062 (6)	0.0240 (6)	−0.0015 (6)
O4	0.0329 (6)	0.0409 (8)	0.0502 (8)	−0.0147 (5)	0.0146 (6)	−0.0045 (6)
O5	0.0479 (7)	0.0338 (7)	0.0374 (7)	−0.0034 (6)	0.0165 (6)	−0.0104 (5)
O6	0.0447 (8)	0.0527 (8)	0.0495 (8)	−0.0079 (6)	0.0318 (7)	−0.0105 (6)
N3	0.0205 (6)	0.0339 (8)	0.0359 (8)	−0.0008 (5)	0.0100 (6)	0.0047 (6)
N5	0.0296 (7)	0.0329 (8)	0.0303 (7)	0.0034 (6)	0.0121 (6)	−0.0026 (6)
C11	0.0183 (7)	0.0253 (8)	0.0254 (8)	0.0021 (6)	0.0053 (6)	0.0007 (6)
C12	0.0204 (7)	0.0281 (8)	0.0261 (8)	0.0032 (6)	0.0083 (6)	0.0013 (6)
C13	0.0171 (7)	0.0280 (8)	0.0296 (8)	−0.0005 (6)	0.0082 (6)	0.0049 (6)
C14	0.0207 (7)	0.0253 (8)	0.0286 (8)	−0.0008 (6)	0.0048 (6)	0.0004 (6)
C15	0.0224 (7)	0.0279 (8)	0.0225 (7)	0.0029 (6)	0.0074 (6)	0.0007 (6)
C16	0.0182 (7)	0.0277 (8)	0.0270 (8)	0.0016 (6)	0.0086 (6)	0.0027 (6)
C17	0.0202 (7)	0.0257 (8)	0.0279 (8)	0.0031 (6)	0.0045 (6)	−0.0009 (6)
N1	0.0161 (6)	0.0276 (7)	0.0323 (7)	−0.0014 (5)	0.0064 (5)	−0.0014 (6)
C2	0.0224 (7)	0.0314 (9)	0.0270 (8)	0.0004 (6)	0.0071 (6)	−0.0005 (6)
C3	0.0220 (7)	0.0299 (9)	0.0297 (8)	−0.0014 (6)	0.0101 (6)	0.0021 (6)
C4	0.0155 (7)	0.0231 (8)	0.0306 (8)	0.0028 (5)	0.0059 (6)	0.0000 (6)
C5	0.0209 (7)	0.0336 (9)	0.0298 (8)	0.0006 (6)	0.0105 (6)	−0.0036 (7)
C6	0.0201 (7)	0.0343 (9)	0.0350 (9)	−0.0006 (6)	0.0128 (6)	−0.0007 (7)
C7	0.0184 (7)	0.0262 (8)	0.0333 (8)	0.0005 (6)	0.0064 (6)	−0.0015 (6)

Geometric parameters (Å, º)

O1—C17	1.2834 (18)	C15—C16	1.385 (2)
O1—H1	0.8400	C16—H116	0.9500
O2—C17	1.2230 (18)	N1—C6	1.337 (2)
O3—N3	1.2223 (18)	N1—C2	1.3388 (19)
O4—N3	1.2267 (18)	N1—H1A	0.8800
O5—N5	1.2286 (18)	C2—C3	1.377 (2)
O6—N5	1.2234 (17)	C2—H2	0.9500
N3—C13	1.4714 (19)	C3—C4	1.391 (2)
N5—C15	1.4707 (19)	C3—H3	0.9500
C11—C12	1.390 (2)	C4—C5	1.397 (2)
C11—C16	1.395 (2)	C4—C7	1.507 (2)
C11—C17	1.515 (2)	C5—C6	1.381 (2)
C12—C13	1.383 (2)	C5—H5	0.9500
C12—H12	0.9500	C6—H6	0.9500
C13—C14	1.380 (2)	C7—C7^i	1.544 (3)
C14—C15	1.384 (2)	C7—H7A	0.9900
C14—H14	0.9500	C7—H7B	0.9900
C17—O1—H1	109.5	O2—C17—C11	119.54 (14)
O3—N3—O4	124.08 (13)	O1—C17—C11	113.59 (13)
O3—N3—C13	118.08 (14)	C6—N1—C2	119.99 (14)
O4—N3—C13	117.81 (13)	C6—N1—H1A	120.0
O6—N5—O5	124.16 (13)	C2—N1—H1A	120.0
O6—N5—C15	118.09 (14)	N1—C2—C3	121.44 (14)
O5—N5—C15	117.75 (13)	N1—C2—H2	119.3
C12—C11—C16	120.01 (14)	C3—C2—H2	119.3
C12—C11—C17	118.72 (13)	C2—C3—C4	119.89 (14)
C16—C11—C17	121.27 (13)	C2—C3—H3	120.1
C13—C12—C11	118.86 (14)	C4—C3—H3	120.1
C13—C12—H12	120.6	C3—C4—C5	117.59 (14)
C11—C12—H12	120.6	C3—C4—C7	120.80 (13)
C14—C13—C12	122.90 (14)	C5—C4—C7	121.61 (14)
C14—C13—N3	118.46 (14)	C6—C5—C4	119.70 (14)
C12—C13—N3	118.54 (13)	C6—C5—H5	120.2
C13—C14—C15	116.76 (15)	C4—C5—H5	120.2
C13—C14—H14	121.6	N1—C6—C5	121.36 (14)
C15—C14—H14	121.6	N1—C6—H6	119.3
C14—C15—C16	122.74 (14)	C5—C6—H6	119.3
C14—C15—N5	117.85 (14)	C4—C7—C7^i	111.76 (16)
C16—C15—N5	119.31 (13)	C4—C7—H7A	109.3
C15—C16—C11	118.72 (13)	C7^i—C7—H7A	109.3
C15—C16—H116	120.6	C4—C7—H7B	109.3
C11—C16—H116	120.6	C7^i—C7—H7B	109.3
O2—C17—O1	126.87 (15)	H7A—C7—H7B	107.9
C16—C11—C12—C13	0.6 (2)	N5—C15—C16—C11	175.91 (13)
C17—C11—C12—C13	179.35 (13)	C12—C11—C16—C15	−0.2 (2)
C11—C12—C13—C14	−0.4 (2)	C17—C11—C16—C15	−178.91 (13)
C11—C12—C13—N3	−176.71 (13)	C12—C11—C17—O2	−1.0 (2)
O3—N3—C13—C14	−177.84 (14)	C16—C11—C17—O2	177.81 (14)
O4—N3—C13—C14	0.2 (2)	C12—C11—C17—O1	178.61 (13)
O3—N3—C13—C12	−1.3 (2)	C16—C11—C17—O1	−2.6 (2)
O4—N3—C13—C12	176.73 (14)	C6—N1—C2—C3	−1.0 (2)
C12—C13—C14—C15	−0.2 (2)	N1—C2—C3—C4	0.0 (2)
N3—C13—C14—C15	176.10 (13)	C2—C3—C4—C5	1.5 (2)
C13—C14—C15—C16	0.7 (2)	C2—C3—C4—C7	−177.91 (14)
C13—C14—C15—N5	−175.77 (13)	C3—C4—C5—C6	−1.9 (2)
O6—N5—C15—C14	−175.48 (14)	C7—C4—C5—C6	177.42 (14)
O5—N5—C15—C14	4.8 (2)	C2—N1—C6—C5	0.5 (2)
O6—N5—C15—C16	7.9 (2)	C4—C5—C6—N1	1.0 (2)
O5—N5—C15—C16	−171.77 (14)	C3—C4—C7—C7^i	68.6 (2)
C14—C15—C16—C11	−0.5 (2)	C5—C4—C7—C7^i	−110.74 (19)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.70	2.521 (2)	167
N1—H1A···O1	0.88	1.65	2.521 (2)	170
C5—H5···O2^ii	0.95	2.39	3.241 (2)	148

Symmetry code: (ii) −x+2, −y+2, −z+1.

(7) 3,5-Dinitrobenzoic acid–trans-1,2-bis(4'-pyridyl)ethene (2/1)

Crystal data

C12H12N2·2(C7H3N2O6)	Z = 1
Mr = 606.46	F(000) = 312
Triclinic, P1	Dx = 1.585 Mg m^−3
a = 4.7297 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3973 (6) Å	Cell parameters from 6274 reflections
c = 14.8365 (6) Å	θ = 2.9–25.5°
α = 104.528 (3)°	µ = 0.13 mm^−1
β = 94.086 (3)°	T = 150 K
γ = 92.793 (3)°	Plate, colourless
V = 635.20 (6) Å^3	0.16 × 0.12 × 0.06 mm

Data collection

Kappa-CCD diffractometer	2360 independent reflections
Radiation source: fine-focus sealed X-ray tube	1733 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ϕ scans and ω scans with κ offsets	θmax = 25.5°, θmin = 2.9°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→5
Tmin = 0.980, Tmax = 0.992	k = −11→11
6274 measured reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0419P)^2 + 0.1435P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2360 reflections	Δρmax = 0.19 e Å^−3
200 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (4)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
O1	−0.4520 (3)	0.99731 (16)	0.74083 (9)	0.0344 (4)
O2	−0.5752 (3)	1.14157 (17)	0.64666 (9)	0.0381 (4)
O3	−1.2960 (3)	1.49312 (17)	0.75141 (9)	0.0397 (4)
O4	−1.4340 (3)	1.52770 (17)	0.89105 (9)	0.0359 (4)
O5	−1.0746 (3)	1.24390 (18)	1.09520 (9)	0.0403 (4)
O6	−0.7447 (3)	1.09490 (17)	1.05409 (9)	0.0387 (4)
N3	−1.2896 (3)	1.46710 (19)	0.82858 (11)	0.0271 (4)
N7	−0.9144 (4)	1.18180 (19)	1.03874 (10)	0.0285 (4)
C1	−0.7668 (4)	1.1775 (2)	0.79395 (12)	0.0217 (4)
C2	−0.9368 (4)	1.2861 (2)	0.77770 (12)	0.0236 (5)
C3	−1.1025 (4)	1.3558 (2)	0.84703 (12)	0.0219 (4)
C4	−1.1016 (4)	1.3232 (2)	0.93260 (12)	0.0229 (5)
C5	−0.9260 (4)	1.2164 (2)	0.94694 (12)	0.0227 (5)
C6	−0.7611 (4)	1.1414 (2)	0.87950 (12)	0.0229 (5)
C7	−0.5850 (4)	1.1009 (2)	0.71892 (13)	0.0248 (5)
N11	−0.1274 (3)	0.84418 (18)	0.63557 (10)	0.0250 (4)
C12	0.0048 (4)	0.7513 (2)	0.67697 (13)	0.0273 (5)
C13	0.1904 (4)	0.6559 (2)	0.63231 (13)	0.0281 (5)
C14	0.2477 (4)	0.6542 (2)	0.54107 (12)	0.0233 (5)
C15	0.1116 (4)	0.7539 (2)	0.50010 (12)	0.0264 (5)
C16	−0.0767 (4)	0.8445 (2)	0.54816 (12)	0.0267 (5)
C17	0.4396 (4)	0.5551 (2)	0.48670 (13)	0.0260 (5)
H2	−0.9400	1.3125	0.7199	0.028*
H4	−1.2162	1.3718	0.9794	0.027*
H6	−0.6464	1.0667	0.8913	0.028*
H11	−0.2895	0.9262	0.6766	0.030*
H12	−0.0314	0.7517	0.7392	0.033*
H13	0.2799	0.5909	0.6634	0.034*
H15	0.1494	0.7591	0.4389	0.032*
H16	−0.1734	0.9090	0.5185	0.032*
H17	0.4813	0.5705	0.4280	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0380 (9)	0.0327 (10)	0.0355 (8)	0.0156 (7)	0.0144 (6)	0.0089 (7)
O2	0.0438 (9)	0.0459 (11)	0.0275 (8)	0.0129 (8)	0.0123 (7)	0.0106 (7)
O3	0.0521 (10)	0.0382 (10)	0.0332 (8)	0.0158 (8)	−0.0003 (7)	0.0158 (7)
O4	0.0348 (9)	0.0325 (10)	0.0413 (8)	0.0146 (7)	0.0105 (7)	0.0066 (7)
O5	0.0485 (10)	0.0486 (11)	0.0277 (8)	0.0165 (8)	0.0172 (7)	0.0106 (7)
O6	0.0439 (10)	0.0408 (11)	0.0361 (8)	0.0150 (8)	0.0008 (7)	0.0169 (7)
N3	0.0260 (9)	0.0231 (10)	0.0313 (9)	0.0030 (8)	−0.0012 (7)	0.0060 (8)
N7	0.0328 (10)	0.0283 (11)	0.0249 (9)	0.0035 (9)	0.0026 (7)	0.0075 (8)
C1	0.0182 (10)	0.0224 (12)	0.0230 (10)	0.0002 (9)	0.0021 (8)	0.0035 (8)
C2	0.0242 (11)	0.0251 (12)	0.0204 (9)	−0.0002 (9)	0.0009 (8)	0.0043 (8)
C3	0.0201 (10)	0.0197 (11)	0.0250 (10)	0.0029 (8)	−0.0012 (8)	0.0047 (8)
C4	0.0216 (10)	0.0193 (12)	0.0250 (10)	0.0024 (9)	0.0040 (8)	0.0001 (8)
C5	0.0237 (11)	0.0242 (12)	0.0201 (9)	0.0010 (9)	0.0017 (8)	0.0056 (8)
C6	0.0213 (10)	0.0210 (12)	0.0260 (10)	0.0037 (9)	0.0017 (8)	0.0049 (8)
C7	0.0217 (11)	0.0258 (13)	0.0245 (10)	0.0005 (9)	0.0036 (8)	0.0016 (9)
N11	0.0249 (9)	0.0239 (10)	0.0263 (9)	0.0053 (8)	0.0078 (7)	0.0040 (7)
C12	0.0299 (11)	0.0288 (13)	0.0239 (10)	0.0060 (10)	0.0047 (8)	0.0067 (9)
C13	0.0294 (11)	0.0293 (13)	0.0275 (10)	0.0085 (10)	0.0032 (8)	0.0090 (9)
C14	0.0192 (10)	0.0228 (12)	0.0250 (10)	−0.0004 (9)	0.0025 (8)	0.0012 (8)
C15	0.0284 (11)	0.0296 (13)	0.0211 (10)	0.0029 (10)	0.0060 (8)	0.0049 (8)
C16	0.0268 (11)	0.0256 (13)	0.0286 (10)	0.0028 (9)	0.0024 (8)	0.0083 (9)
C17	0.0239 (11)	0.0286 (13)	0.0242 (10)	0.0009 (9)	0.0029 (8)	0.0044 (8)

Geometric parameters (Å, º)

O1—C7	1.280 (2)	C5—C6	1.385 (3)
O2—C7	1.228 (2)	C6—H6	0.95
O3—N3	1.228 (2)	N11—C16	1.336 (2)
O4—N3	1.230 (2)	N11—C12	1.341 (2)
O5—N7	1.227 (2)	N11—H11	1.20
O6—N7	1.223 (2)	C12—C13	1.370 (3)
N3—C3	1.466 (2)	C12—H12	0.95
N7—C5	1.475 (2)	C13—C14	1.396 (3)
C1—C2	1.386 (3)	C13—H13	0.95
C1—C6	1.393 (3)	C14—C15	1.397 (3)
C1—C7	1.514 (3)	C14—C17	1.466 (3)
C2—C3	1.388 (3)	C15—C16	1.373 (3)
C2—H2	0.95	C15—H15	0.95
C3—C4	1.379 (3)	C16—H16	0.95
C4—C5	1.381 (3)	C17—C17^i	1.337 (4)
C4—H4	0.95	C17—H17	0.95
O3—N3—O4	123.75 (17)	O2—C7—O1	127.06 (18)
O3—N3—C3	118.25 (16)	O2—C7—C1	119.84 (18)
O4—N3—C3	117.99 (16)	O1—C7—C1	113.10 (16)
O6—N7—O5	124.27 (16)	C16—N11—C12	119.27 (17)
O6—N7—C5	118.23 (15)	C16—N11—H11	120.4
O5—N7—C5	117.50 (16)	C12—N11—H11	120.4
C2—C1—C6	119.86 (17)	N11—C12—C13	122.02 (17)
C2—C1—C7	119.62 (16)	N11—C12—H12	119.0
C6—C1—C7	120.51 (17)	C13—C12—H12	119.0
C1—C2—C3	119.13 (17)	C12—C13—C14	119.88 (18)
C1—C2—H2	120.4	C12—C13—H13	120.1
C3—C2—H2	120.4	C14—C13—H13	120.1
C4—C3—C2	122.60 (18)	C13—C14—C15	117.03 (17)
C4—C3—N3	118.32 (16)	C13—C14—C17	124.18 (18)
C2—C3—N3	119.08 (17)	C15—C14—C17	118.79 (16)
C3—C4—C5	116.68 (17)	C16—C15—C14	120.06 (17)
C3—C4—H4	121.7	C16—C15—H15	120.0
C5—C4—H4	121.7	C14—C15—H15	120.0
C4—C5—C6	123.04 (17)	N11—C16—C15	121.70 (19)
C4—C5—N7	117.98 (16)	N11—C16—H16	119.2
C6—C5—N7	118.98 (17)	C15—C16—H16	119.2
C5—C6—C1	118.67 (18)	C17^i—C17—C14	125.1 (2)
C5—C6—H6	120.7	C17^i—C17—H17	117.5
C1—C6—H6	120.7	C14—C17—H17	117.5
C6—C1—C2—C3	−0.9 (3)	N7—C5—C6—C1	−178.18 (16)
C7—C1—C2—C3	−179.95 (17)	C2—C1—C6—C5	−0.4 (3)
C1—C2—C3—C4	1.1 (3)	C7—C1—C6—C5	178.62 (18)
C1—C2—C3—N3	−177.94 (17)	C2—C1—C7—O2	4.6 (3)
O3—N3—C3—C4	−178.03 (17)	C6—C1—C7—O2	−174.40 (18)
O4—N3—C3—C4	1.0 (3)	C2—C1—C7—O1	−176.07 (18)
O3—N3—C3—C2	1.1 (3)	C6—C1—C7—O1	4.9 (3)
O4—N3—C3—C2	−179.84 (17)	C16—N11—C12—C13	−0.2 (3)
C2—C3—C4—C5	0.0 (3)	N11—C12—C13—C14	0.4 (3)
N3—C3—C4—C5	179.09 (17)	C12—C13—C14—C15	0.8 (3)
C3—C4—C5—C6	−1.4 (3)	C12—C13—C14—C17	−179.14 (19)
C3—C4—C5—N7	178.39 (16)	C13—C14—C15—C16	−2.2 (3)
O6—N7—C5—C4	−174.96 (18)	C17—C14—C15—C16	177.75 (18)
O5—N7—C5—C4	4.2 (3)	C12—N11—C16—C15	−1.2 (3)
O6—N7—C5—C6	4.8 (3)	C14—C15—C16—N11	2.5 (3)
O5—N7—C5—C6	−175.97 (18)	C13—C14—C17—C17^i	7.2 (4)
C4—C5—C6—C1	1.6 (3)	C15—C14—C17—C17^i	−172.8 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O1	1.20	1.33	2.509 (2)	164
C12—H12···O5^ii	0.95	2.46	3.362 (2)	158

Symmetry code: (ii) −x−1, −y+2, −z+2.