Supramolecular heterosynthon assemblies of ortho-phenyl­enedi­amine with substituted aromatic carb­oxy­lic acids

Co-crystallization experiments conducted between ortho-phenyl­enedi­amine (OPDA) and five substituted aromatic acids (phthalic acid, salicylic acid, 4-hy­droxy­benzoic acid, 4-nitro­benzoic acid and 3,5-di­nitro­benzoic acid) reveal the formation of supramolecular networks constructed from acid–base heterosynthons of ortho-phenyl­enedi­ammonium cations with respective aromatic anions. All of these coformers are generally regarded as safe (GRAS) molecules. The five reported crystal structures are sustained predominantly by intermolecular N⁺−H...O⁻, N—H...O⁻ and N—H...O hydrogen-bonding interactions; in addition intramolecular O—H...O and intermolecular O—H...O, O—H...O⁻ and C—H...O interactions contribute to the formation of various networks. Five 1:1 salts [NH₂C₆H₄NH₃]⁺·[COOHC₆H₄COO]⁻ (1); [NH₂C₆H₄NH₃]⁺·[OHC₆H₄COO]⁻ (2); [{NH₂C₆H₄NH₂}₂·{OHC₆H₄COOH}₂·{NH₂C₆H₄NH₃}⁺₂·{OHC₆H₄COO}⁻₂] (OPDPHB) (3); [NH₂C₆H₄NH₃]⁺·[NO₂C₆H₄COO]⁻ (4) and [NH₂C₆H₄NH₃]⁺·[(NO₂)₂C₆H₄COO]⁻ (5) were isolated as single crystals by the slow evaporation method and were characterized using spectroscopic and X-ray crystallographic techniques. X-ray diffraction studies confirmed the formation of salts. The pK_a difference between the amine and respective acid favours the transfer of a proton from the acid to the amine, which leads to the formation of the anion and the cation. The interactions between these ions resulted in a stable heterosynthon in each case. The asymmetric units of salts (1), (2), (4) and (5) contain one anion and one cation each, but salt (3) consists of two anions, two cations and two neutral species in its asymmetric unit. A polymorph of salt (3) was also isolated from the crystallization of the ground material from liquid-assisted grinding [{NH₂C₆H₄NH₂}·{NH₂C₆H₄NH₃}⁺·{OHC₆H₄COO}⁻] (OPDPHB 3P). The polymorph crystallized in the monoclinic non-centrosymmetric space group P2₁. The liquid-assisted grinding experiments using a 1:1 ratio also revealed the formation of the expected salts, except salt (3), where this product matches with polymorph (OPDPHB 3P).

Computing details

Data collection: Bruker SMART for OPDP; CrysAlis PRO, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) for OPDPHB. Cell refinement: Bruker SMART for OPDP; SAINT v6.45A (Bruker, 2003) for OPDS; CrysAlis PRO, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) for OPDPHB. Data reduction: Bruker SAINT for OPDP; SAINT v6.45A (Bruker, 2003) for OPDS; CrysAlis PRO, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) for OPDPHB. For all structures, program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(OPDP)

Crystal data

C6H9N2·C8H5O4	Z = 2
Mr = 274.27	F(000) = 288
Triclinic, P1	Dx = 1.443 Mg m^−3
a = 4.101 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.892 (7) Å	Cell parameters from 2931 reflections
c = 13.092 (8) Å	θ = 2.4–27.3°
α = 93.491 (9)°	µ = 0.11 mm^−1
β = 97.769 (10)°	T = 298 K
γ = 90.28 (1)°	Plate, colorless
V = 631.4 (6) Å^3	0.34 × 0.28 × 0.22 mm

Data collection

CCD area detector diffractometer	2083 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.022
Absorption correction: multi-scan sadabs	θmax = 26.0°, θmin = 1.6°
Tmin = 0.808, Tmax = 0.965	h = −5→5
6461 measured reflections	k = −14→14
2454 independent reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0614P)^2 + 0.157P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2454 reflections	Δρmax = 0.18 e Å^−3
205 parameters	Δρmin = −0.18 e Å^−3
2 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.7675 (4)	0.27622 (13)	0.67449 (11)	0.0410 (4)
C2	0.6774 (4)	0.30757 (13)	0.57379 (12)	0.0438 (4)
C3	0.4735 (4)	0.23309 (16)	0.50677 (13)	0.0550 (4)
H3	0.4089	0.2514	0.4390	0.066*
C4	0.3674 (5)	0.13347 (18)	0.53930 (16)	0.0647 (5)
H4A	0.2322	0.0851	0.4934	0.078*
C5	0.4585 (5)	0.10441 (16)	0.63904 (17)	0.0638 (5)
H5	0.3850	0.0369	0.6607	0.077*
C6	0.6609 (4)	0.17664 (15)	0.70694 (14)	0.0528 (4)
H6	0.7245	0.1576	0.7745	0.063*
C7	0.3657 (4)	0.69881 (12)	0.81981 (11)	0.0386 (3)
C8	0.4509 (4)	0.75212 (12)	0.91934 (11)	0.0393 (3)
C9	0.3354 (4)	0.86061 (14)	0.93783 (13)	0.0502 (4)
H9	0.3889	0.8963	1.0032	0.060*
C10	0.1454 (5)	0.91679 (15)	0.86309 (15)	0.0567 (5)
H10	0.0760	0.9896	0.8776	0.068*
C11	0.0593 (4)	0.86458 (16)	0.76696 (14)	0.0552 (4)
H11	−0.0713	0.9014	0.7160	0.066*
C12	0.1674 (4)	0.75711 (14)	0.74640 (12)	0.0478 (4)
H12	0.1058	0.7222	0.6811	0.057*
C13	0.4632 (4)	0.58254 (13)	0.78054 (12)	0.0455 (4)
C14	0.6576 (4)	0.70810 (14)	1.01291 (11)	0.0465 (4)
N1	0.9850 (4)	0.35076 (13)	0.74647 (11)	0.0475 (4)
N2	0.7952 (4)	0.40550 (14)	0.54008 (12)	0.0563 (4)
O1	0.3527 (4)	0.54750 (11)	0.69199 (9)	0.0689 (4)
O2	0.6540 (4)	0.52337 (11)	0.83864 (10)	0.0673 (4)
O3	0.6955 (4)	0.76662 (12)	1.09393 (9)	0.0730 (5)
O4	0.7964 (4)	0.61215 (11)	1.00889 (9)	0.0634 (4)
H1A	1.097 (5)	0.3090 (17)	0.8009 (14)	0.069 (6)*
H1B	0.883 (5)	0.409 (2)	0.7783 (17)	0.074 (6)*
H1C	1.139 (6)	0.393 (2)	0.7145 (18)	0.077 (7)*
H2A	0.715 (5)	0.4222 (18)	0.4722 (18)	0.076 (6)*
H2B	0.844 (6)	0.460 (2)	0.5824 (19)	0.082 (8)*
H4	0.750 (6)	0.5731 (18)	0.9417 (14)	0.086 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0455 (8)	0.0409 (8)	0.0354 (8)	0.0105 (6)	0.0033 (6)	−0.0024 (6)
C2	0.0465 (8)	0.0470 (9)	0.0370 (8)	0.0107 (7)	0.0033 (6)	−0.0007 (6)
C3	0.0536 (10)	0.0645 (11)	0.0426 (9)	0.0061 (8)	−0.0035 (7)	−0.0086 (8)
C4	0.0556 (11)	0.0638 (12)	0.0707 (13)	−0.0037 (9)	0.0033 (9)	−0.0158 (10)
C5	0.0658 (12)	0.0485 (10)	0.0795 (14)	−0.0033 (9)	0.0200 (10)	0.0011 (9)
C6	0.0625 (10)	0.0488 (9)	0.0494 (10)	0.0122 (8)	0.0141 (8)	0.0071 (7)
C7	0.0422 (8)	0.0400 (8)	0.0335 (7)	−0.0023 (6)	0.0037 (6)	0.0034 (6)
C8	0.0436 (8)	0.0380 (8)	0.0356 (8)	0.0004 (6)	0.0029 (6)	0.0033 (6)
C9	0.0607 (10)	0.0420 (9)	0.0457 (9)	0.0047 (7)	0.0017 (7)	−0.0022 (7)
C10	0.0638 (11)	0.0411 (9)	0.0645 (11)	0.0117 (8)	0.0045 (9)	0.0052 (8)
C11	0.0552 (10)	0.0563 (10)	0.0529 (10)	0.0088 (8)	−0.0029 (8)	0.0170 (8)
C12	0.0509 (9)	0.0530 (10)	0.0378 (8)	−0.0007 (7)	−0.0017 (7)	0.0062 (7)
C13	0.0578 (9)	0.0424 (8)	0.0351 (8)	−0.0015 (7)	0.0037 (7)	−0.0008 (6)
C14	0.0577 (10)	0.0465 (9)	0.0335 (8)	0.0058 (7)	0.0002 (7)	0.0001 (6)
N1	0.0589 (9)	0.0466 (8)	0.0343 (7)	0.0113 (7)	−0.0024 (6)	−0.0013 (6)
N2	0.0753 (11)	0.0523 (9)	0.0385 (8)	−0.0001 (7)	−0.0050 (7)	0.0086 (7)
O1	0.1014 (10)	0.0581 (8)	0.0403 (7)	0.0067 (7)	−0.0094 (7)	−0.0112 (6)
O2	0.1004 (10)	0.0495 (7)	0.0465 (7)	0.0264 (7)	−0.0068 (7)	−0.0074 (5)
O3	0.1076 (11)	0.0670 (9)	0.0366 (7)	0.0300 (8)	−0.0134 (7)	−0.0111 (6)
O4	0.0918 (10)	0.0535 (7)	0.0389 (7)	0.0257 (7)	−0.0109 (6)	−0.0028 (5)

Geometric parameters (Å, º)

C1—C2	1.394 (2)	C9—C10	1.375 (2)
C1—C6	1.371 (2)	C10—H10	0.9300
C1—N1	1.461 (2)	C10—C11	1.370 (3)
C2—C3	1.397 (2)	C11—H11	0.9300
C2—N2	1.378 (2)	C11—C12	1.378 (3)
C3—H3	0.9300	C12—H12	0.9300
C3—C4	1.372 (3)	C13—O1	1.233 (2)
C4—H4A	0.9300	C13—O2	1.263 (2)
C4—C5	1.374 (3)	C14—O3	1.224 (2)
C5—H5	0.9300	C14—O4	1.279 (2)
C5—C6	1.385 (3)	N1—H1A	0.960 (15)
C6—H6	0.9300	N1—H1B	0.91 (2)
C7—C8	1.413 (2)	N1—H1C	0.96 (2)
C7—C12	1.393 (2)	N2—H2A	0.94 (2)
C7—C13	1.520 (2)	N2—H2B	0.84 (3)
C8—C9	1.395 (2)	O2—H4	1.442 (17)
C8—C14	1.515 (2)	O4—H4	0.965 (16)
C9—H9	0.9300
C2—C1—N1	118.96 (15)	C9—C10—H10	120.3
C6—C1—C2	121.65 (15)	C11—C10—C9	119.45 (17)
C6—C1—N1	119.39 (14)	C11—C10—H10	120.3
C1—C2—C3	117.23 (16)	C10—C11—H11	120.3
N2—C2—C1	121.59 (15)	C10—C11—C12	119.49 (15)
N2—C2—C3	121.12 (16)	C12—C11—H11	120.3
C2—C3—H3	119.5	C7—C12—H12	118.8
C4—C3—C2	121.07 (17)	C11—C12—C7	122.45 (15)
C4—C3—H3	119.5	C11—C12—H12	118.8
C3—C4—H4A	119.6	O1—C13—C7	119.03 (14)
C3—C4—C5	120.71 (18)	O1—C13—O2	121.09 (16)
C5—C4—H4A	119.6	O2—C13—C7	119.88 (14)
C4—C5—H5	120.3	O3—C14—C8	119.00 (15)
C4—C5—C6	119.36 (18)	O3—C14—O4	119.34 (15)
C6—C5—H5	120.3	O4—C14—C8	121.65 (14)
C1—C6—C5	119.99 (17)	C1—N1—H1A	110.3 (13)
C1—C6—H6	120.0	C1—N1—H1B	115.2 (14)
C5—C6—H6	120.0	C1—N1—H1C	114.3 (14)
C8—C7—C13	128.02 (13)	H1A—N1—H1B	105.9 (18)
C12—C7—C8	118.02 (14)	H1A—N1—H1C	110.8 (18)
C12—C7—C13	113.96 (14)	H1B—N1—H1C	100 (2)
C7—C8—C14	128.96 (14)	C2—N2—H2A	116.3 (14)
C9—C8—C7	118.08 (14)	C2—N2—H2B	119.2 (16)
C9—C8—C14	112.96 (14)	H2A—N2—H2B	117 (2)
C8—C9—H9	118.8	C13—O2—H4	114.8 (9)
C10—C9—C8	122.50 (16)	C14—O4—H4	112.5 (14)
C10—C9—H9	118.8
C1—C2—C3—C4	0.0 (2)	C9—C8—C14—O4	−176.79 (16)
C2—C1—C6—C5	0.0 (2)	C9—C10—C11—C12	−0.7 (3)
C2—C3—C4—C5	0.1 (3)	C10—C11—C12—C7	−0.6 (3)
C3—C4—C5—C6	−0.3 (3)	C12—C7—C8—C9	−0.9 (2)
C4—C5—C6—C1	0.2 (3)	C12—C7—C8—C14	179.32 (15)
C6—C1—C2—C3	−0.1 (2)	C12—C7—C13—O1	−3.1 (2)
C6—C1—C2—N2	−177.36 (16)	C12—C7—C13—O2	177.06 (16)
C7—C8—C9—C10	−0.4 (3)	C13—C7—C8—C9	179.28 (15)
C7—C8—C14—O3	−177.89 (17)	C13—C7—C8—C14	−0.5 (3)
C7—C8—C14—O4	3.0 (3)	C13—C7—C12—C11	−178.75 (15)
C8—C7—C12—C11	1.4 (2)	C14—C8—C9—C10	179.42 (16)
C8—C7—C13—O1	176.67 (16)	N1—C1—C2—C3	178.92 (14)
C8—C7—C13—O2	−3.1 (3)	N1—C1—C2—N2	1.7 (2)
C8—C9—C10—C11	1.2 (3)	N1—C1—C6—C5	−179.04 (15)
C9—C8—C14—O3	2.3 (2)	N2—C2—C3—C4	177.31 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3^i	0.96 (2)	1.81 (2)	2.768 (2)	178 (2)
N1—H1A···O3^i	0.96 (2)	1.81 (2)	2.768 (2)	178 (2)
N1—H1A···O4^i	0.96 (2)	2.59 (2)	3.210 (3)	123 (2)
N1—H1A···O4^i	0.96 (2)	2.59 (2)	3.210 (3)	123 (2)
N1—H1B···O2	0.91 (2)	1.86 (2)	2.771 (2)	177 (2)
N1—H1B···O2	0.91 (2)	1.86 (2)	2.771 (2)	177 (2)
N1—H1C···O1^ii	0.96 (2)	2.08 (2)	2.952 (3)	150 (2)
N1—H1C···O1^ii	0.96 (2)	2.08 (2)	2.952 (3)	150 (2)
N2—H2A···O1^iii	0.94 (2)	2.18 (2)	3.102 (3)	166.4 (19)
N2—H2A···O1^iii	0.94 (2)	2.18 (2)	3.102 (3)	166.4 (19)
O4—H4···O2	0.97 (2)	1.44 (2)	2.404 (2)	174 (2)
O4—H4···O2	0.97 (2)	1.44 (2)	2.404 (2)	174 (2)

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

(OPDS)

Crystal data

C7H5O3·C6H9N2	F(000) = 520
Mr = 246.26	Dx = 1.343 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.7832 (7) Å	Cell parameters from 4567 reflections
b = 11.6783 (17) Å	θ = 2.6–26.6°
c = 21.859 (3) Å	µ = 0.10 mm^−1
β = 93.999 (2)°	T = 298 K
V = 1218.1 (3) Å^3	Block, dark brown
Z = 4	0.42 × 0.36 × 0.32 mm

Data collection

CCD area detector diffractometer	2926 independent reflections
Radiation source: sealed X-ray tube	2396 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 7.9 pixels mm^-1	θmax = 28.3°, θmin = 1.9°
ω scans	h = −6→6
Absorption correction: multi-scan SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0727 before and 0.0392 after correction. The Ratio of minimum to maximum transmission is 0.8673. The λ/2 correction factor is 0.0015.'	k = −14→15
Tmin = 0.867, Tmax = 0.876	l = −28→28
13780 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.0654P)^2 + 0.1663P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.131	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.24 e Å^−3
2926 reflections	Δρmin = −0.22 e Å^−3
188 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.043 (5)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	0.6820 (2)	1.03695 (9)	0.58996 (5)	0.0573 (3)
O2	0.8410 (2)	0.86066 (9)	0.57940 (4)	0.0576 (3)
O3	0.6376 (3)	0.69526 (10)	0.63796 (6)	0.0707 (4)
C7	0.5149 (2)	0.89212 (11)	0.65426 (6)	0.0425 (3)
C8	0.4949 (3)	0.77526 (12)	0.66796 (6)	0.0512 (3)
C9	0.3239 (4)	0.73905 (16)	0.71308 (8)	0.0678 (5)
H9	0.3106	0.6615	0.7221	0.081*
C10	0.1753 (4)	0.81708 (19)	0.74431 (8)	0.0750 (5)
H10	0.0600	0.7920	0.7741	0.090*
C11	0.1945 (3)	0.93237 (18)	0.73215 (7)	0.0689 (5)
H11	0.0941	0.9849	0.7539	0.083*
C12	0.3635 (3)	0.96940 (13)	0.68761 (6)	0.0529 (4)
H12	0.3767	1.0474	0.6796	0.064*
C13	0.6906 (2)	0.93347 (12)	0.60505 (6)	0.0437 (3)
N1	0.1629 (2)	0.13494 (9)	0.54758 (5)	0.0434 (3)
N2	−0.2651 (3)	0.27322 (14)	0.49169 (6)	0.0629 (4)
C1	0.1306 (2)	0.25389 (11)	0.56681 (6)	0.0410 (3)
C2	−0.0834 (3)	0.31938 (12)	0.53795 (6)	0.0470 (3)
C3	−0.1146 (3)	0.43065 (13)	0.55965 (7)	0.0590 (4)
H3	−0.2565	0.4767	0.5418	0.071*
C4	0.0599 (4)	0.47384 (13)	0.60682 (8)	0.0622 (4)
H4	0.0333	0.5481	0.6206	0.075*
C5	0.2730 (3)	0.40836 (14)	0.63380 (7)	0.0610 (4)
H5	0.3924	0.4383	0.6652	0.073*
C6	0.3074 (3)	0.29751 (12)	0.61367 (6)	0.0504 (3)
H6	0.4502	0.2522	0.6317	0.060*
H3A	0.743 (4)	0.7406 (19)	0.6108 (10)	0.090 (7)*
H1A	0.327 (4)	0.1033 (15)	0.5664 (8)	0.061 (4)*
H1B	0.171 (3)	0.1331 (14)	0.5047 (8)	0.060 (4)*
H1C	0.011 (4)	0.0919 (15)	0.5598 (8)	0.063 (5)*
H2A	−0.193 (4)	0.2193 (18)	0.4653 (9)	0.080 (6)*
H2B	−0.371 (4)	0.3210 (19)	0.4726 (10)	0.082 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0463 (5)	0.0556 (6)	0.0710 (7)	0.0034 (4)	0.0102 (5)	0.0153 (5)
O2	0.0550 (6)	0.0695 (7)	0.0493 (5)	0.0138 (5)	0.0105 (4)	−0.0052 (5)
O3	0.0841 (8)	0.0467 (6)	0.0810 (8)	0.0100 (5)	0.0025 (7)	−0.0030 (5)
C7	0.0375 (6)	0.0490 (7)	0.0403 (6)	0.0018 (5)	−0.0019 (5)	−0.0007 (5)
C8	0.0506 (7)	0.0503 (8)	0.0514 (7)	−0.0006 (6)	−0.0060 (6)	0.0010 (6)
C9	0.0701 (10)	0.0678 (10)	0.0644 (9)	−0.0185 (8)	−0.0029 (8)	0.0165 (8)
C10	0.0620 (10)	0.1073 (15)	0.0569 (9)	−0.0130 (9)	0.0117 (8)	0.0128 (9)
C11	0.0578 (9)	0.0987 (14)	0.0517 (8)	0.0111 (8)	0.0138 (7)	−0.0032 (8)
C12	0.0518 (8)	0.0597 (8)	0.0476 (7)	0.0078 (6)	0.0051 (6)	−0.0033 (6)
C13	0.0360 (6)	0.0528 (7)	0.0417 (6)	0.0035 (5)	−0.0012 (5)	−0.0003 (5)
N1	0.0403 (6)	0.0431 (6)	0.0474 (6)	0.0044 (4)	0.0069 (5)	−0.0007 (5)
N2	0.0533 (7)	0.0729 (9)	0.0611 (8)	0.0182 (6)	−0.0070 (6)	−0.0041 (7)
C1	0.0386 (6)	0.0420 (6)	0.0436 (6)	0.0022 (5)	0.0117 (5)	0.0014 (5)
C2	0.0420 (6)	0.0515 (7)	0.0484 (7)	0.0067 (5)	0.0103 (5)	0.0033 (6)
C3	0.0588 (8)	0.0534 (8)	0.0663 (9)	0.0181 (7)	0.0154 (7)	0.0065 (7)
C4	0.0707 (10)	0.0467 (8)	0.0713 (10)	0.0049 (7)	0.0196 (8)	−0.0089 (7)
C5	0.0622 (9)	0.0599 (9)	0.0615 (9)	−0.0035 (7)	0.0081 (7)	−0.0138 (7)
C6	0.0451 (7)	0.0526 (8)	0.0536 (8)	0.0027 (6)	0.0048 (6)	−0.0024 (6)

Geometric parameters (Å, º)

O1—C13	1.2527 (16)	N1—H1A	0.938 (19)
O2—C13	1.2693 (16)	N1—H1B	0.940 (18)
O3—C8	1.3532 (18)	N1—H1C	0.938 (19)
O3—H3A	0.96 (2)	N2—C2	1.3951 (19)
C7—C8	1.4019 (19)	N2—H2A	0.94 (2)
C7—C12	1.3943 (18)	N2—H2B	0.84 (2)
C7—C13	1.4908 (18)	C1—C2	1.3929 (18)
C8—C9	1.390 (2)	C1—C6	1.3795 (18)
C9—H9	0.9300	C2—C3	1.395 (2)
C9—C10	1.367 (3)	C3—H3	0.9300
C10—H10	0.9300	C3—C4	1.376 (2)
C10—C11	1.377 (3)	C4—H4	0.9300
C11—H11	0.9300	C4—C5	1.374 (2)
C11—C12	1.378 (2)	C5—H5	0.9300
C12—H12	0.9300	C5—C6	1.381 (2)
N1—C1	1.4627 (16)	C6—H6	0.9300
C8—O3—H3A	102.9 (13)	H1A—N1—H1B	109.7 (14)
C8—C7—C13	121.31 (12)	H1A—N1—H1C	107.8 (15)
C12—C7—C8	118.21 (13)	H1B—N1—H1C	111.0 (15)
C12—C7—C13	120.48 (12)	C2—N2—H2A	117.9 (12)
O3—C8—C7	121.63 (13)	C2—N2—H2B	115.1 (14)
O3—C8—C9	118.38 (15)	H2A—N2—H2B	112.0 (18)
C9—C8—C7	119.99 (14)	C2—C1—N1	118.70 (11)
C8—C9—H9	119.9	C6—C1—N1	119.51 (11)
C10—C9—C8	120.23 (16)	C6—C1—C2	121.77 (12)
C10—C9—H9	119.9	C1—C2—N2	121.14 (13)
C9—C10—H10	119.6	C1—C2—C3	116.75 (13)
C9—C10—C11	120.76 (15)	C3—C2—N2	122.04 (13)
C11—C10—H10	119.6	C2—C3—H3	119.2
C10—C11—H11	120.2	C4—C3—C2	121.50 (14)
C10—C11—C12	119.59 (16)	C4—C3—H3	119.2
C12—C11—H11	120.2	C3—C4—H4	119.6
C7—C12—H12	119.4	C5—C4—C3	120.70 (14)
C11—C12—C7	121.20 (15)	C5—C4—H4	119.6
C11—C12—H12	119.4	C4—C5—H5	120.4
O1—C13—O2	122.62 (12)	C4—C5—C6	119.10 (15)
O1—C13—C7	119.52 (11)	C6—C5—H5	120.4
O2—C13—C7	117.85 (12)	C1—C6—C5	120.15 (13)
C1—N1—H1A	110.5 (10)	C1—C6—H6	119.9
C1—N1—H1B	108.7 (10)	C5—C6—H6	119.9
C1—N1—H1C	109.1 (10)
O3—C8—C9—C10	−179.75 (14)	C13—C7—C8—C9	−178.41 (12)
C7—C8—C9—C10	−0.1 (2)	C13—C7—C12—C11	178.32 (13)
C8—C7—C12—C11	−1.1 (2)	N1—C1—C2—N2	0.21 (18)
C8—C7—C13—O1	172.99 (12)	N1—C1—C2—C3	177.13 (11)
C8—C7—C13—O2	−5.97 (17)	N1—C1—C6—C5	−177.66 (12)
C8—C9—C10—C11	−0.7 (3)	N2—C2—C3—C4	177.63 (14)
C9—C10—C11—C12	0.6 (3)	C1—C2—C3—C4	0.7 (2)
C10—C11—C12—C7	0.3 (2)	C2—C1—C6—C5	0.9 (2)
C12—C7—C8—O3	−179.40 (12)	C2—C3—C4—C5	0.5 (2)
C12—C7—C8—C9	1.00 (19)	C3—C4—C5—C6	−1.1 (2)
C12—C7—C13—O1	−6.40 (18)	C4—C5—C6—C1	0.4 (2)
C12—C7—C13—O2	174.64 (12)	C6—C1—C2—N2	−178.36 (13)
C13—C7—C8—O3	1.19 (19)	C6—C1—C2—C3	−1.43 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.96 (2)	1.64 (2)	2.5476 (17)	154.5 (19)
N1—H1A···O1^i	0.938 (19)	1.904 (19)	2.8309 (15)	169.6 (15)
N1—H1B···O2^ii	0.940 (18)	1.838 (19)	2.7749 (16)	174.6 (15)
N1—H1C···O1^iii	0.938 (19)	1.861 (19)	2.7847 (15)	167.6 (16)
N2—H2A···O2^ii	0.94 (2)	2.21 (2)	3.0681 (17)	151.8 (16)

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

(OPDPHB)

Crystal data

C7H6O3·C7H5O3·C6H9N2·C6H8N2	Z = 4
Mr = 492.52	F(000) = 1040
Triclinic, P1	Dx = 1.342 Mg m^−3
a = 9.9374 (5) Å	Cu Kα radiation, λ = 1.54184 Å
b = 14.3212 (6) Å	Cell parameters from 5251 reflections
c = 18.2929 (11) Å	θ = 4.5–71.6°
α = 72.196 (4)°	µ = 0.80 mm^−1
β = 81.185 (5)°	T = 298 K
γ = 82.068 (4)°	Plate, pale yellow
V = 2437.9 (2) Å^3	0.32 × 0.28 × 0.22 mm

Data collection

Xcalibur, Eos, Gemini diffractometer	9322 independent reflections
Radiation source: Enhance (Cu) X-ray Source	7257 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 16.3291 pixels mm^-1	θmax = 72.2°, θmin = 3.5°
ω scans	h = −12→8
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −17→15
Tmin = 0.301, Tmax = 1.000	l = −22→22
15886 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.066P)^2 + 0.211P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
9322 reflections	Δρmax = 0.20 e Å^−3
690 parameters	Δρmin = −0.29 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
H2AA	0.547 (3)	1.1937 (17)	0.1584 (14)	0.071 (7)*
C1A	0.72740 (19)	1.05528 (12)	0.12641 (10)	0.0417 (4)
C2A	0.58847 (18)	1.05977 (12)	0.15208 (10)	0.0413 (4)
C3A	0.5274 (2)	0.97152 (14)	0.17780 (12)	0.0541 (5)
H3A	0.4345	0.9721	0.1955	0.065*
C4A	0.6028 (3)	0.88384 (15)	0.17728 (13)	0.0667 (6)
H4A	0.5605	0.8257	0.1953	0.080*
C5A	0.7402 (3)	0.88065 (14)	0.15044 (14)	0.0672 (6)
H5A	0.7900	0.8210	0.1495	0.081*
C6A	0.8035 (2)	0.96734 (13)	0.12490 (11)	0.0529 (5)
H6A	0.8963	0.9663	0.1069	0.064*
N1A	0.80069 (16)	1.14368 (10)	0.10319 (9)	0.0477 (4)
H1AA	0.8370	1.1549	0.0541	0.057*
H1AB	0.8669	1.1348	0.1331	0.057*
H1AC	0.7427	1.1951	0.1083	0.057*
N2A	0.50788 (17)	1.14910 (12)	0.14930 (10)	0.0505 (4)
H2AB	0.4343	1.1380	0.1809	0.061*
H2BA	1.109 (2)	0.3473 (16)	0.4657 (13)	0.064 (7)*
C1B	0.92964 (18)	0.44449 (13)	0.32941 (10)	0.0442 (4)
C2B	1.00944 (18)	0.43593 (14)	0.38773 (10)	0.0457 (4)
C3B	1.0443 (2)	0.52311 (16)	0.39611 (13)	0.0610 (5)
H3B	1.0955	0.5199	0.4354	0.073*
C4B	1.0044 (3)	0.61325 (17)	0.34748 (15)	0.0722 (6)
H4B	1.0284	0.6703	0.3542	0.087*
C5B	0.9296 (3)	0.61958 (16)	0.28920 (14)	0.0710 (6)
H5B	0.9046	0.6807	0.2555	0.085*
C6B	0.8911 (2)	0.53533 (15)	0.28035 (12)	0.0577 (5)
H6B	0.8389	0.5397	0.2411	0.069*
N1B	0.88069 (17)	0.35639 (11)	0.32299 (9)	0.0520 (4)
H1BA	0.8485	0.3699	0.2777	0.062*
H1BB	0.8143	0.3366	0.3611	0.062*
H1BC	0.9493	0.3088	0.3262	0.062*
N2B	1.04695 (19)	0.34308 (13)	0.43876 (10)	0.0565 (4)
H2BB	1.0668	0.3003	0.4133	0.068*
C7A	0.30590 (18)	−0.01875 (12)	0.61584 (10)	0.0423 (4)
C8A	0.2788 (2)	0.04838 (13)	0.65914 (10)	0.0474 (4)
H8A	0.2577	0.0258	0.7125	0.057*
C9A	0.2833 (2)	0.14779 (13)	0.62316 (11)	0.0501 (4)
H9A	0.2650	0.1920	0.6524	0.060*
C10A	0.31498 (18)	0.18227 (12)	0.54375 (11)	0.0443 (4)
C11A	0.3399 (2)	0.11636 (13)	0.50027 (10)	0.0483 (4)
H11A	0.3600	0.1391	0.4468	0.058*
C12A	0.3348 (2)	0.01721 (13)	0.53624 (10)	0.0476 (4)
H12A	0.3510	−0.0265	0.5066	0.057*
C13A	0.3058 (2)	−0.12635 (13)	0.65172 (10)	0.0462 (4)
O1A	0.3324 (2)	−0.18485 (10)	0.61453 (9)	0.0830 (6)
O2A	0.27523 (16)	−0.15490 (9)	0.72689 (7)	0.0560 (4)
H2A	0.2805	−0.2153	0.7423	0.084*
O3A	0.31799 (16)	0.28125 (9)	0.51111 (8)	0.0564 (3)
H3AA	0.3481	0.2925	0.4653	0.085*
H1CA	0.390 (3)	0.690 (2)	0.5519 (18)	0.103 (11)*
H2CA	0.627 (3)	0.6426 (18)	0.6732 (15)	0.080 (9)*
C1C	0.43749 (19)	0.54968 (14)	0.59811 (11)	0.0470 (4)
C2C	0.54162 (19)	0.55525 (13)	0.63910 (10)	0.0448 (4)
C3C	0.6192 (2)	0.46863 (16)	0.67292 (11)	0.0574 (5)
H3C	0.6902	0.4708	0.6999	0.069*
C4C	0.5923 (3)	0.37907 (16)	0.66709 (14)	0.0715 (7)
H4C	0.6455	0.3217	0.6898	0.086*
C5C	0.4875 (3)	0.37473 (17)	0.62800 (16)	0.0728 (7)
H5C	0.4682	0.3144	0.6249	0.087*
C6C	0.4118 (2)	0.45895 (16)	0.59384 (14)	0.0622 (5)
H6C	0.3411	0.4557	0.5670	0.075*
N1C	0.35399 (19)	0.63541 (14)	0.56392 (11)	0.0583 (4)
H1CB	0.3206	0.6268	0.5260	0.070*
N2C	0.5717 (2)	0.64817 (13)	0.64095 (11)	0.0571 (4)
H2CB	0.4967	0.6829	0.6498	0.069*
H1DA	0.181 (2)	0.2078 (16)	0.0830 (14)	0.062 (7)*
C1D	0.19137 (18)	0.07206 (13)	0.09702 (10)	0.0434 (4)
C2D	0.10995 (18)	0.04139 (12)	0.16756 (10)	0.0429 (4)
C3D	0.1130 (2)	−0.05874 (14)	0.20653 (12)	0.0540 (5)
H3D	0.0613	−0.0796	0.2544	0.065*
C4D	0.1910 (3)	−0.12721 (15)	0.17557 (14)	0.0639 (6)
H4D	0.1906	−0.1940	0.2019	0.077*
C5D	0.2699 (2)	−0.09708 (16)	0.10559 (14)	0.0638 (6)
H5D	0.3226	−0.1434	0.0844	0.077*
C6D	0.2708 (2)	0.00173 (15)	0.06688 (12)	0.0551 (5)
H6D	0.3253	0.0217	0.0199	0.066*
N1D	0.18724 (18)	0.17352 (12)	0.05420 (11)	0.0527 (4)
H1DB	0.2609	0.1835	0.0220	0.063*
N2D	0.01739 (19)	0.11077 (13)	0.19505 (11)	0.0528 (4)
C7D	0.13001 (19)	0.47876 (12)	0.13437 (10)	0.0417 (4)
C8D	0.20936 (19)	0.55014 (13)	0.13754 (10)	0.0456 (4)
H8D	0.2874	0.5313	0.1628	0.055*
C9D	0.1728 (2)	0.64830 (13)	0.10348 (11)	0.0480 (4)
H9D	0.2270	0.6954	0.1052	0.058*
C10D	0.05582 (19)	0.67749 (12)	0.06667 (10)	0.0446 (4)
C11D	−0.0234 (2)	0.60685 (14)	0.06265 (11)	0.0520 (5)
H11D	−0.1019	0.6259	0.0377	0.062*
C12D	0.0149 (2)	0.50846 (13)	0.09578 (11)	0.0492 (4)
H12D	−0.0373	0.4613	0.0922	0.059*
C13D	0.1661 (2)	0.37240 (13)	0.17065 (11)	0.0483 (4)
O1D	0.10800 (19)	0.30967 (10)	0.15870 (10)	0.0726 (5)
O2D	0.26277 (16)	0.35195 (10)	0.21515 (10)	0.0641 (4)
H2D	0.2703	0.2926	0.2372	0.096*
O3D	0.02358 (15)	0.77592 (9)	0.03488 (9)	0.0565 (3)
H3DA	−0.0439	0.7844	0.0120	0.085*
C7C	0.35792 (16)	0.51930 (11)	0.88572 (9)	0.0369 (3)
C8C	0.39652 (19)	0.45337 (12)	0.84250 (10)	0.0429 (4)
H8C	0.3942	0.4750	0.7893	0.051*
C9C	0.4382 (2)	0.35628 (12)	0.87763 (10)	0.0470 (4)
H9C	0.4644	0.3129	0.8480	0.056*
C10C	0.44125 (17)	0.32299 (12)	0.95673 (10)	0.0411 (4)
C11C	0.40016 (19)	0.38731 (12)	1.00066 (10)	0.0430 (4)
H11C	0.3995	0.3649	1.0541	0.052*
C12C	0.36022 (18)	0.48474 (12)	0.96505 (10)	0.0422 (4)
H12C	0.3344	0.5280	0.9948	0.051*
C13C	0.32152 (18)	0.62658 (12)	0.84890 (10)	0.0423 (4)
O1C	0.32784 (17)	0.68365 (9)	0.88749 (8)	0.0599 (4)
O2C	0.28998 (16)	0.65470 (9)	0.78056 (7)	0.0548 (3)
O3C	0.48388 (16)	0.22609 (9)	0.98844 (8)	0.0551 (3)
H3CA	0.4805	0.2143	1.0354	0.083*
C7B	0.81934 (19)	−0.03694 (13)	0.63485 (10)	0.0432 (4)
C8B	0.93863 (19)	0.00187 (14)	0.59499 (11)	0.0496 (4)
H8B	1.0156	−0.0406	0.5875	0.060*
C9B	0.9459 (2)	0.10205 (14)	0.56616 (11)	0.0507 (4)
H9B	1.0273	0.1267	0.5400	0.061*
C10B	0.8314 (2)	0.16599 (13)	0.57633 (11)	0.0472 (4)
C11B	0.7100 (2)	0.12830 (13)	0.61465 (11)	0.0505 (4)
H11B	0.6323	0.1709	0.6206	0.061*
C12B	0.70439 (19)	0.02827 (13)	0.64383 (10)	0.0464 (4)
H12B	0.6229	0.0037	0.6699	0.056*
C13B	0.8152 (2)	−0.14520 (13)	0.66819 (11)	0.0492 (4)
O1B	0.91505 (17)	−0.20098 (10)	0.65139 (9)	0.0673 (4)
O2B	0.70881 (15)	−0.17529 (10)	0.71267 (9)	0.0616 (4)
O3B	0.83288 (16)	0.26595 (9)	0.55151 (10)	0.0629 (4)
H3BA	0.8965	0.2807	0.5172	0.094*
H2DA	−0.018 (2)	0.0830 (17)	0.2400 (14)	0.065 (7)*
H2DB	0.050 (3)	0.166 (2)	0.1916 (16)	0.088 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0515 (10)	0.0362 (8)	0.0364 (8)	−0.0025 (7)	−0.0122 (7)	−0.0064 (7)
C2A	0.0481 (10)	0.0413 (9)	0.0363 (8)	−0.0059 (7)	−0.0118 (7)	−0.0096 (7)
C3A	0.0629 (12)	0.0536 (11)	0.0504 (11)	−0.0188 (9)	−0.0123 (9)	−0.0134 (8)
C4A	0.0958 (18)	0.0431 (11)	0.0663 (14)	−0.0210 (11)	−0.0243 (13)	−0.0101 (9)
C5A	0.1000 (19)	0.0378 (10)	0.0689 (14)	0.0075 (11)	−0.0308 (13)	−0.0191 (9)
C6A	0.0604 (12)	0.0472 (10)	0.0522 (11)	0.0066 (9)	−0.0161 (9)	−0.0164 (8)
N1A	0.0447 (8)	0.0415 (8)	0.0522 (9)	−0.0023 (6)	−0.0036 (7)	−0.0088 (7)
N2A	0.0456 (9)	0.0478 (9)	0.0585 (10)	−0.0030 (7)	−0.0055 (7)	−0.0168 (7)
C1B	0.0420 (9)	0.0483 (10)	0.0421 (9)	0.0015 (7)	−0.0026 (7)	−0.0166 (8)
C2B	0.0399 (9)	0.0548 (10)	0.0404 (9)	−0.0030 (8)	−0.0001 (7)	−0.0136 (8)
C3B	0.0595 (13)	0.0709 (14)	0.0582 (12)	−0.0175 (10)	−0.0035 (10)	−0.0235 (10)
C4B	0.0853 (17)	0.0563 (13)	0.0766 (16)	−0.0184 (12)	0.0052 (13)	−0.0236 (12)
C5B	0.0852 (17)	0.0509 (12)	0.0652 (14)	0.0020 (11)	0.0003 (12)	−0.0079 (10)
C6B	0.0625 (13)	0.0592 (12)	0.0457 (11)	0.0078 (10)	−0.0075 (9)	−0.0122 (9)
N1B	0.0532 (9)	0.0550 (9)	0.0510 (9)	0.0055 (7)	−0.0143 (7)	−0.0208 (7)
N2B	0.0548 (10)	0.0623 (10)	0.0521 (10)	0.0017 (8)	−0.0173 (8)	−0.0141 (8)
C7A	0.0435 (9)	0.0414 (9)	0.0401 (9)	−0.0009 (7)	−0.0064 (7)	−0.0098 (7)
C8A	0.0592 (11)	0.0436 (9)	0.0379 (9)	−0.0036 (8)	−0.0077 (8)	−0.0093 (7)
C9A	0.0649 (12)	0.0431 (9)	0.0455 (10)	−0.0064 (8)	−0.0097 (9)	−0.0155 (8)
C10A	0.0440 (9)	0.0371 (8)	0.0489 (10)	−0.0042 (7)	−0.0129 (8)	−0.0046 (7)
C11A	0.0560 (11)	0.0480 (10)	0.0363 (9)	−0.0062 (8)	−0.0050 (8)	−0.0052 (7)
C12A	0.0582 (11)	0.0436 (9)	0.0397 (9)	−0.0026 (8)	−0.0039 (8)	−0.0122 (7)
C13A	0.0537 (11)	0.0390 (9)	0.0429 (9)	0.0001 (8)	−0.0038 (8)	−0.0106 (7)
O1A	0.1499 (18)	0.0422 (8)	0.0508 (9)	−0.0002 (9)	0.0033 (10)	−0.0158 (7)
O2A	0.0835 (10)	0.0376 (6)	0.0413 (7)	−0.0058 (7)	−0.0031 (6)	−0.0052 (5)
O3A	0.0713 (9)	0.0389 (7)	0.0541 (8)	−0.0089 (6)	−0.0105 (7)	−0.0034 (6)
C1C	0.0430 (10)	0.0482 (10)	0.0466 (10)	−0.0028 (8)	0.0002 (8)	−0.0125 (8)
C2C	0.0453 (10)	0.0481 (10)	0.0370 (9)	−0.0040 (8)	0.0041 (7)	−0.0109 (7)
C3C	0.0512 (11)	0.0670 (13)	0.0451 (10)	0.0077 (9)	−0.0022 (8)	−0.0106 (9)
C4C	0.0763 (16)	0.0492 (12)	0.0720 (15)	0.0150 (11)	0.0070 (12)	−0.0096 (10)
C5C	0.0724 (16)	0.0522 (12)	0.0946 (19)	−0.0062 (11)	0.0081 (14)	−0.0310 (12)
C6C	0.0554 (12)	0.0628 (13)	0.0742 (14)	−0.0107 (10)	0.0001 (10)	−0.0302 (11)
N1C	0.0539 (10)	0.0562 (10)	0.0626 (11)	−0.0023 (8)	−0.0159 (8)	−0.0111 (8)
N2C	0.0573 (10)	0.0583 (10)	0.0599 (11)	−0.0076 (8)	−0.0078 (9)	−0.0219 (8)
C1D	0.0430 (9)	0.0434 (9)	0.0454 (9)	−0.0049 (7)	−0.0148 (7)	−0.0106 (7)
C2D	0.0441 (9)	0.0426 (9)	0.0460 (10)	−0.0051 (7)	−0.0124 (7)	−0.0148 (7)
C3D	0.0646 (12)	0.0478 (10)	0.0489 (11)	−0.0101 (9)	−0.0143 (9)	−0.0071 (8)
C4D	0.0797 (15)	0.0395 (10)	0.0762 (15)	−0.0008 (10)	−0.0285 (12)	−0.0150 (10)
C5D	0.0655 (13)	0.0553 (12)	0.0812 (16)	0.0076 (10)	−0.0206 (12)	−0.0352 (11)
C6D	0.0505 (11)	0.0651 (12)	0.0546 (11)	−0.0035 (9)	−0.0074 (9)	−0.0250 (10)
N1D	0.0527 (10)	0.0464 (9)	0.0549 (10)	−0.0103 (7)	−0.0061 (8)	−0.0064 (8)
N2D	0.0540 (10)	0.0500 (9)	0.0566 (11)	−0.0078 (8)	−0.0003 (8)	−0.0206 (8)
C7D	0.0503 (10)	0.0389 (9)	0.0369 (8)	−0.0111 (7)	−0.0001 (7)	−0.0117 (7)
C8D	0.0496 (10)	0.0444 (9)	0.0451 (10)	−0.0099 (8)	−0.0087 (8)	−0.0126 (7)
C9D	0.0553 (11)	0.0421 (9)	0.0514 (10)	−0.0154 (8)	−0.0098 (8)	−0.0144 (8)
C10D	0.0501 (10)	0.0397 (9)	0.0406 (9)	−0.0095 (7)	−0.0011 (7)	−0.0064 (7)
C11D	0.0509 (11)	0.0512 (10)	0.0524 (11)	−0.0121 (8)	−0.0128 (9)	−0.0067 (8)
C12D	0.0535 (11)	0.0463 (10)	0.0504 (10)	−0.0190 (8)	−0.0062 (8)	−0.0118 (8)
C13D	0.0600 (11)	0.0403 (9)	0.0457 (10)	−0.0110 (8)	−0.0022 (8)	−0.0134 (8)
O1D	0.1024 (13)	0.0430 (7)	0.0799 (11)	−0.0204 (8)	−0.0314 (10)	−0.0132 (7)
O2D	0.0716 (10)	0.0408 (7)	0.0801 (11)	−0.0065 (7)	−0.0269 (8)	−0.0084 (7)
O3D	0.0601 (9)	0.0413 (7)	0.0632 (9)	−0.0082 (6)	−0.0121 (7)	−0.0043 (6)
C7C	0.0362 (8)	0.0335 (8)	0.0397 (8)	−0.0059 (6)	−0.0052 (7)	−0.0071 (6)
C8C	0.0515 (10)	0.0414 (9)	0.0341 (8)	−0.0064 (7)	−0.0044 (7)	−0.0082 (7)
C9C	0.0584 (11)	0.0382 (9)	0.0452 (10)	−0.0020 (8)	−0.0010 (8)	−0.0166 (7)
C10C	0.0389 (9)	0.0327 (8)	0.0479 (10)	−0.0037 (6)	−0.0016 (7)	−0.0077 (7)
C11C	0.0526 (10)	0.0391 (9)	0.0336 (8)	−0.0040 (7)	−0.0052 (7)	−0.0051 (7)
C12C	0.0505 (10)	0.0361 (8)	0.0403 (9)	−0.0019 (7)	−0.0055 (7)	−0.0126 (7)
C13C	0.0442 (9)	0.0346 (8)	0.0460 (10)	−0.0060 (7)	−0.0075 (7)	−0.0067 (7)
O1C	0.0905 (11)	0.0339 (6)	0.0579 (8)	0.0003 (6)	−0.0227 (8)	−0.0129 (6)
O2C	0.0780 (10)	0.0378 (6)	0.0458 (7)	−0.0060 (6)	−0.0217 (7)	−0.0012 (5)
O3C	0.0674 (9)	0.0341 (6)	0.0544 (8)	0.0045 (6)	−0.0027 (7)	−0.0055 (5)
C7B	0.0477 (10)	0.0430 (9)	0.0367 (9)	0.0069 (7)	−0.0095 (7)	−0.0111 (7)
C8B	0.0455 (10)	0.0509 (10)	0.0470 (10)	0.0121 (8)	−0.0079 (8)	−0.0125 (8)
C9B	0.0455 (10)	0.0530 (11)	0.0481 (10)	0.0003 (8)	−0.0041 (8)	−0.0094 (8)
C10B	0.0524 (11)	0.0430 (9)	0.0441 (10)	0.0021 (8)	−0.0118 (8)	−0.0096 (8)
C11B	0.0475 (10)	0.0439 (10)	0.0564 (11)	0.0098 (8)	−0.0075 (8)	−0.0146 (8)
C12B	0.0442 (10)	0.0450 (9)	0.0463 (10)	0.0031 (7)	−0.0040 (8)	−0.0118 (8)
C13B	0.0550 (11)	0.0455 (10)	0.0451 (10)	0.0094 (8)	−0.0128 (8)	−0.0132 (8)
O1B	0.0747 (10)	0.0482 (8)	0.0670 (9)	0.0206 (7)	−0.0014 (8)	−0.0140 (7)
O2B	0.0583 (9)	0.0427 (7)	0.0715 (10)	0.0028 (6)	−0.0012 (7)	−0.0050 (6)
O3B	0.0638 (9)	0.0429 (7)	0.0741 (10)	−0.0003 (6)	−0.0077 (7)	−0.0077 (7)

Geometric parameters (Å, º)

C1A—C2A	1.388 (3)	N2C—H2CA	0.84 (3)
C1A—C6A	1.382 (2)	N2C—H2CB	0.8602
C1A—N1A	1.464 (2)	C1D—C2D	1.394 (3)
C2A—C3A	1.395 (2)	C1D—C6D	1.389 (3)
C2A—N2A	1.404 (2)	C1D—N1D	1.423 (2)
C3A—H3A	0.9300	C2D—C3D	1.391 (2)
C3A—C4A	1.373 (3)	C2D—N2D	1.413 (2)
C4A—H4A	0.9300	C3D—H3D	0.9300
C4A—C5A	1.378 (4)	C3D—C4D	1.370 (3)
C5A—H5A	0.9300	C4D—H4D	0.9300
C5A—C6A	1.388 (3)	C4D—C5D	1.374 (3)
C6A—H6A	0.9300	C5D—H5D	0.9300
N1A—H1AA	0.8900	C5D—C6D	1.376 (3)
N1A—H1AB	0.8900	C6D—H6D	0.9300
N1A—H1AC	0.8900	N1D—H1DA	0.81 (2)
N2A—H2AA	0.86 (2)	N1D—H1DB	0.8648
N2A—H2AB	0.8608	N2D—H2DA	0.84 (2)
C1B—C2B	1.391 (3)	N2D—H2DB	0.88 (3)
C1B—C6B	1.378 (3)	C7D—C8D	1.394 (2)
C1B—N1B	1.456 (2)	C7D—C12D	1.384 (3)
C2B—C3B	1.398 (3)	C7D—C13D	1.481 (2)
C2B—N2B	1.410 (2)	C8D—H8D	0.9300
C3B—H3B	0.9300	C8D—C9D	1.374 (2)
C3B—C4B	1.371 (3)	C9D—H9D	0.9300
C4B—H4B	0.9300	C9D—C10D	1.383 (3)
C4B—C5B	1.365 (4)	C10D—C11D	1.390 (3)
C5B—H5B	0.9300	C10D—O3D	1.363 (2)
C5B—C6B	1.376 (3)	C11D—H11D	0.9300
C6B—H6B	0.9300	C11D—C12D	1.378 (3)
N1B—H1BA	0.8900	C12D—H12D	0.9300
N1B—H1BB	0.8900	C13D—O1D	1.221 (2)
N1B—H1BC	0.8900	C13D—O2D	1.299 (2)
N2B—H2BA	0.86 (2)	O2D—H2D	0.8200
N2B—H2BB	0.8625	O3D—H3DA	0.8200
C7A—C8A	1.397 (2)	C7C—C8C	1.388 (2)
C7A—C12A	1.386 (2)	C7C—C12C	1.385 (2)
C7A—C13A	1.479 (2)	C7C—C13C	1.494 (2)
C8A—H8A	0.9300	C8C—H8C	0.9300
C8A—C9A	1.378 (2)	C8C—C9C	1.376 (2)
C9A—H9A	0.9300	C9C—H9C	0.9300
C9A—C10A	1.385 (3)	C9C—C10C	1.382 (2)
C10A—C11A	1.385 (3)	C10C—C11C	1.382 (2)
C10A—O3A	1.362 (2)	C10C—O3C	1.3647 (19)
C11A—H11A	0.9300	C11C—H11C	0.9300
C11A—C12A	1.375 (2)	C11C—C12C	1.378 (2)
C12A—H12A	0.9300	C12C—H12C	0.9300
C13A—O1A	1.211 (2)	C13C—O1C	1.245 (2)
C13A—O2A	1.309 (2)	C13C—O2C	1.265 (2)
O2A—H2A	0.8200	O3C—H3CA	0.8200
O3A—H3AA	0.8200	C7B—C8B	1.384 (3)
C1C—C2C	1.392 (3)	C7B—C12B	1.395 (2)
C1C—C6C	1.385 (3)	C7B—C13B	1.486 (2)
C1C—N1C	1.413 (2)	C8B—H8B	0.9300
C2C—C3C	1.389 (3)	C8B—C9B	1.377 (3)
C2C—N2C	1.415 (2)	C9B—H9B	0.9300
C3C—H3C	0.9300	C9B—C10B	1.386 (3)
C3C—C4C	1.384 (3)	C10B—C11B	1.388 (3)
C4C—H4C	0.9300	C10B—O3B	1.365 (2)
C4C—C5C	1.369 (4)	C11B—H11B	0.9300
C5C—H5C	0.9300	C11B—C12B	1.373 (2)
C5C—C6C	1.358 (3)	C12B—H12B	0.9300
C6C—H6C	0.9300	C13B—O1B	1.247 (2)
N1C—H1CA	0.85 (3)	C13B—O2B	1.270 (2)
N1C—H1CB	0.8604	O3B—H3BA	0.8200
C2A—C1A—N1A	120.87 (15)	C1C—N1C—H1CA	116 (2)
C6A—C1A—C2A	121.84 (17)	C1C—N1C—H1CB	109.1
C6A—C1A—N1A	117.23 (17)	H2CA—N2C—H2CB	112.2
C1A—C2A—C3A	117.61 (17)	C2C—N2C—H2CA	111.8 (17)
C1A—C2A—N2A	122.58 (16)	C2C—N2C—H2CB	109.3
C3A—C2A—N2A	119.73 (18)	C2D—C1D—N1D	120.54 (17)
C2A—C3A—H3A	119.6	C6D—C1D—C2D	119.11 (17)
C4A—C3A—C2A	120.8 (2)	C6D—C1D—N1D	120.25 (18)
C4A—C3A—H3A	119.6	C1D—C2D—N2D	119.88 (16)
C3A—C4A—H4A	119.5	C3D—C2D—C1D	118.96 (17)
C3A—C4A—C5A	121.0 (2)	C3D—C2D—N2D	120.92 (18)
C5A—C4A—H4A	119.5	C2D—C3D—H3D	119.4
C4A—C5A—H5A	120.3	C4D—C3D—C2D	121.1 (2)
C4A—C5A—C6A	119.32 (19)	C4D—C3D—H3D	119.4
C6A—C5A—H5A	120.3	C3D—C4D—H4D	120.1
C1A—C6A—C5A	119.4 (2)	C3D—C4D—C5D	119.89 (19)
C1A—C6A—H6A	120.3	C5D—C4D—H4D	120.1
C5A—C6A—H6A	120.3	C4D—C5D—H5D	120.0
C1A—N1A—H1AA	109.5	C4D—C5D—C6D	120.0 (2)
C1A—N1A—H1AB	109.5	C6D—C5D—H5D	120.0
C1A—N1A—H1AC	109.5	C1D—C6D—H6D	119.5
H1AA—N1A—H1AB	109.5	C5D—C6D—C1D	120.9 (2)
H1AA—N1A—H1AC	109.5	C5D—C6D—H6D	119.5
H1AB—N1A—H1AC	109.5	H1DA—N1D—H1DB	109.6
H2AA—N2A—H2AB	109.2	C1D—N1D—H1DA	110.6 (17)
C2A—N2A—H2AA	115.8 (17)	C1D—N1D—H1DB	109.2
C2A—N2A—H2AB	109.5	C2D—N2D—H2DA	109.3 (16)
C2B—C1B—N1B	119.18 (16)	C2D—N2D—H2DB	115.4 (18)
C6B—C1B—C2B	120.95 (18)	H2DA—N2D—H2DB	113 (2)
C6B—C1B—N1B	119.80 (18)	C8D—C7D—C13D	121.77 (17)
C1B—C2B—C3B	117.32 (18)	C12D—C7D—C8D	118.87 (16)
C1B—C2B—N2B	120.93 (17)	C12D—C7D—C13D	119.36 (16)
C3B—C2B—N2B	121.66 (19)	C7D—C8D—H8D	119.8
C2B—C3B—H3B	119.3	C9D—C8D—C7D	120.33 (17)
C4B—C3B—C2B	121.3 (2)	C9D—C8D—H8D	119.8
C4B—C3B—H3B	119.3	C8D—C9D—H9D	119.8
C3B—C4B—H4B	119.9	C8D—C9D—C10D	120.43 (16)
C5B—C4B—C3B	120.3 (2)	C10D—C9D—H9D	119.8
C5B—C4B—H4B	119.9	C9D—C10D—C11D	119.68 (17)
C4B—C5B—H5B	120.0	O3D—C10D—C9D	117.85 (16)
C4B—C5B—C6B	119.9 (2)	O3D—C10D—C11D	122.47 (17)
C6B—C5B—H5B	120.1	C10D—C11D—H11D	120.2
C1B—C6B—H6B	119.9	C12D—C11D—C10D	119.64 (18)
C5B—C6B—C1B	120.2 (2)	C12D—C11D—H11D	120.2
C5B—C6B—H6B	119.9	C7D—C12D—H12D	119.5
C1B—N1B—H1BA	109.5	C11D—C12D—C7D	121.02 (17)
C1B—N1B—H1BB	109.5	C11D—C12D—H12D	119.5
C1B—N1B—H1BC	109.5	O1D—C13D—C7D	121.39 (18)
H1BA—N1B—H1BB	109.5	O1D—C13D—O2D	123.43 (18)
H1BA—N1B—H1BC	109.5	O2D—C13D—C7D	115.18 (16)
H1BB—N1B—H1BC	109.5	C13D—O2D—H2D	109.5
H2BA—N2B—H2BB	116.0	C10D—O3D—H3DA	109.5
C2B—N2B—H2BA	110.8 (15)	C8C—C7C—C13C	122.05 (15)
C2B—N2B—H2BB	109.3	C12C—C7C—C8C	118.49 (15)
C8A—C7A—C13A	122.54 (16)	C12C—C7C—C13C	119.38 (15)
C12A—C7A—C8A	118.52 (16)	C7C—C8C—H8C	119.7
C12A—C7A—C13A	118.94 (16)	C9C—C8C—C7C	120.65 (16)
C7A—C8A—H8A	119.8	C9C—C8C—H8C	119.7
C9A—C8A—C7A	120.33 (17)	C8C—C9C—H9C	119.9
C9A—C8A—H8A	119.8	C8C—C9C—C10C	120.27 (16)
C8A—C9A—H9A	119.8	C10C—C9C—H9C	119.9
C8A—C9A—C10A	120.38 (17)	C9C—C10C—C11C	119.68 (15)
C10A—C9A—H9A	119.8	O3C—C10C—C9C	117.76 (15)
C9A—C10A—C11A	119.65 (16)	O3C—C10C—C11C	122.55 (16)
O3A—C10A—C9A	117.99 (16)	C10C—C11C—H11C	120.1
O3A—C10A—C11A	122.35 (17)	C12C—C11C—C10C	119.79 (16)
C10A—C11A—H11A	120.1	C12C—C11C—H11C	120.1
C12A—C11A—C10A	119.88 (17)	C7C—C12C—H12C	119.4
C12A—C11A—H11A	120.1	C11C—C12C—C7C	121.11 (15)
C7A—C12A—H12A	119.4	C11C—C12C—H12C	119.4
C11A—C12A—C7A	121.22 (17)	O1C—C13C—C7C	117.09 (16)
C11A—C12A—H12A	119.4	O1C—C13C—O2C	123.80 (16)
O1A—C13A—C7A	122.69 (17)	O2C—C13C—C7C	119.08 (15)
O1A—C13A—O2A	121.69 (17)	C10C—O3C—H3CA	109.5
O2A—C13A—C7A	115.62 (15)	C8B—C7B—C12B	118.21 (16)
C13A—O2A—H2A	109.5	C8B—C7B—C13B	120.62 (16)
C10A—O3A—H3AA	109.5	C12B—C7B—C13B	121.16 (17)
C2C—C1C—N1C	120.30 (17)	C7B—C8B—H8B	119.3
C6C—C1C—C2C	119.75 (19)	C9B—C8B—C7B	121.47 (17)
C6C—C1C—N1C	119.89 (19)	C9B—C8B—H8B	119.3
C1C—C2C—N2C	119.85 (17)	C8B—C9B—H9B	120.2
C3C—C2C—C1C	118.14 (18)	C8B—C9B—C10B	119.70 (18)
C3C—C2C—N2C	121.87 (19)	C10B—C9B—H9B	120.2
C2C—C3C—H3C	119.5	C9B—C10B—C11B	119.60 (17)
C4C—C3C—C2C	120.9 (2)	O3B—C10B—C9B	122.67 (18)
C4C—C3C—H3C	119.5	O3B—C10B—C11B	117.72 (17)
C3C—C4C—H4C	120.0	C10B—C11B—H11B	119.9
C5C—C4C—C3C	120.1 (2)	C12B—C11B—C10B	120.17 (17)
C5C—C4C—H4C	120.0	C12B—C11B—H11B	119.9
C4C—C5C—H5C	120.2	C7B—C12B—H12B	119.6
C6C—C5C—C4C	119.6 (2)	C11B—C12B—C7B	120.84 (18)
C6C—C5C—H5C	120.2	C11B—C12B—H12B	119.6
C1C—C6C—H6C	119.3	O1B—C13B—C7B	118.82 (18)
C5C—C6C—C1C	121.4 (2)	O1B—C13B—O2B	123.85 (18)
C5C—C6C—H6C	119.3	O2B—C13B—C7B	117.33 (16)
H1CA—N1C—H1CB	113.0	C10B—O3B—H3BA	109.5
C1A—C2A—C3A—C4A	−0.2 (3)	C3D—C4D—C5D—C6D	0.2 (3)
C2A—C1A—C6A—C5A	−0.7 (3)	C4D—C5D—C6D—C1D	−0.9 (3)
C2A—C3A—C4A—C5A	−0.9 (3)	C6D—C1D—C2D—C3D	1.4 (3)
C3A—C4A—C5A—C6A	1.2 (3)	C6D—C1D—C2D—N2D	−173.11 (17)
C4A—C5A—C6A—C1A	−0.4 (3)	N1D—C1D—C2D—C3D	177.77 (17)
C6A—C1A—C2A—C3A	1.0 (3)	N1D—C1D—C2D—N2D	3.2 (3)
C6A—C1A—C2A—N2A	−175.74 (17)	N1D—C1D—C6D—C5D	−176.31 (18)
N1A—C1A—C2A—C3A	−176.06 (16)	N2D—C2D—C3D—C4D	172.38 (19)
N1A—C1A—C2A—N2A	7.2 (3)	C7D—C8D—C9D—C10D	1.0 (3)
N1A—C1A—C6A—C5A	176.45 (17)	C8D—C7D—C12D—C11D	−1.7 (3)
N2A—C2A—C3A—C4A	176.63 (18)	C8D—C7D—C13D—O1D	−169.64 (19)
C1B—C2B—C3B—C4B	−1.7 (3)	C8D—C7D—C13D—O2D	10.3 (3)
C2B—C1B—C6B—C5B	−1.0 (3)	C8D—C9D—C10D—C11D	−1.4 (3)
C2B—C3B—C4B—C5B	−0.3 (4)	C8D—C9D—C10D—O3D	179.09 (17)
C3B—C4B—C5B—C6B	1.6 (4)	C9D—C10D—C11D—C12D	0.4 (3)
C4B—C5B—C6B—C1B	−1.0 (4)	C10D—C11D—C12D—C7D	1.2 (3)
C6B—C1B—C2B—C3B	2.3 (3)	C12D—C7D—C8D—C9D	0.6 (3)
C6B—C1B—C2B—N2B	178.93 (18)	C12D—C7D—C13D—O1D	9.9 (3)
N1B—C1B—C2B—C3B	−174.53 (17)	C12D—C7D—C13D—O2D	−170.14 (18)
N1B—C1B—C2B—N2B	2.1 (3)	C13D—C7D—C8D—C9D	−179.79 (17)
N1B—C1B—C6B—C5B	175.80 (19)	C13D—C7D—C12D—C11D	178.68 (17)
N2B—C2B—C3B—C4B	−178.3 (2)	O3D—C10D—C11D—C12D	179.81 (18)
C7A—C8A—C9A—C10A	−0.2 (3)	C7C—C8C—C9C—C10C	0.4 (3)
C8A—C7A—C12A—C11A	1.4 (3)	C8C—C7C—C12C—C11C	0.2 (3)
C8A—C7A—C13A—O1A	−178.2 (2)	C8C—C7C—C13C—O1C	−159.29 (18)
C8A—C7A—C13A—O2A	1.7 (3)	C8C—C7C—C13C—O2C	18.8 (3)
C8A—C9A—C10A—C11A	1.1 (3)	C8C—C9C—C10C—C11C	1.0 (3)
C8A—C9A—C10A—O3A	179.99 (18)	C8C—C9C—C10C—O3C	−179.78 (17)
C9A—C10A—C11A—C12A	−0.8 (3)	C9C—C10C—C11C—C12C	−1.9 (3)
C10A—C11A—C12A—C7A	−0.4 (3)	C10C—C11C—C12C—C7C	1.3 (3)
C12A—C7A—C8A—C9A	−1.1 (3)	C12C—C7C—C8C—C9C	−1.0 (3)
C12A—C7A—C13A—O1A	1.3 (3)	C12C—C7C—C13C—O1C	17.4 (3)
C12A—C7A—C13A—O2A	−178.76 (18)	C12C—C7C—C13C—O2C	−164.51 (17)
C13A—C7A—C8A—C9A	178.45 (18)	C13C—C7C—C8C—C9C	175.65 (16)
C13A—C7A—C12A—C11A	−178.16 (18)	C13C—C7C—C12C—C11C	−176.58 (16)
O3A—C10A—C11A—C12A	−179.65 (17)	O3C—C10C—C11C—C12C	178.99 (17)
C1C—C2C—C3C—C4C	−1.0 (3)	C7B—C8B—C9B—C10B	−0.7 (3)
C2C—C1C—C6C—C5C	−0.9 (3)	C8B—C7B—C12B—C11B	−0.8 (3)
C2C—C3C—C4C—C5C	−0.4 (3)	C8B—C7B—C13B—O1B	−9.1 (3)
C3C—C4C—C5C—C6C	1.2 (4)	C8B—C7B—C13B—O2B	170.79 (18)
C4C—C5C—C6C—C1C	−0.5 (4)	C8B—C9B—C10B—C11B	−0.8 (3)
C6C—C1C—C2C—C3C	1.7 (3)	C8B—C9B—C10B—O3B	177.76 (18)
C6C—C1C—C2C—N2C	177.46 (18)	C9B—C10B—C11B—C12B	1.5 (3)
N1C—C1C—C2C—C3C	178.77 (17)	C10B—C11B—C12B—C7B	−0.7 (3)
N1C—C1C—C2C—N2C	−5.5 (3)	C12B—C7B—C8B—C9B	1.4 (3)
N1C—C1C—C6C—C5C	−178.0 (2)	C12B—C7B—C13B—O1B	171.96 (18)
N2C—C2C—C3C—C4C	−176.72 (18)	C12B—C7B—C13B—O2B	−8.2 (3)
C1D—C2D—C3D—C4D	−2.1 (3)	C13B—C7B—C8B—C9B	−177.58 (17)
C2D—C1D—C6D—C5D	0.0 (3)	C13B—C7B—C12B—C11B	178.25 (17)
C2D—C3D—C4D—C5D	1.3 (3)	O3B—C10B—C11B—C12B	−177.16 (17)

(OPDPNB)

Crystal data

C7H4NO4·C6H9N2	F(000) = 288
Mr = 275.26	Dx = 1.413 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.881 (2) Å	Cell parameters from 1756 reflections
b = 6.0754 (16) Å	θ = 2.3–25.0°
c = 11.995 (3) Å	µ = 0.11 mm^−1
β = 91.021 (4)°	T = 298 K
V = 647.1 (3) Å^3	Plate
Z = 2	0.38 × 0.12 × 0.09 mm

Data collection

CCD area detector diffractometer	1635 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	Rint = 0.018
Graphite monochromator	θmax = 25.0°, θmin = 1.7°
phi and ω scans	h = −10→10
2914 measured reflections	k = −7→7
2026 independent reflections	l = −14→12

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.069P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.126	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.16 e Å^−3
2026 reflections	Δρmin = −0.16 e Å^−3
201 parameters	Absolute structure: Flack x determined using 533 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61).
5 restraints	Absolute structure parameter: 0.2 (10)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.2701 (4)	0.6539 (6)	0.4059 (3)	0.0339 (10)
C2	0.3039 (4)	0.8534 (7)	0.4586 (3)	0.0360 (10)
C3	0.4283 (5)	0.9672 (8)	0.4204 (4)	0.0456 (12)
H3	0.4525	1.1024	0.4523	0.055*
C4	0.5164 (5)	0.8871 (9)	0.3376 (4)	0.0522 (13)
H4	0.5983	0.9683	0.3135	0.063*
C5	0.4838 (5)	0.6849 (9)	0.2896 (4)	0.0555 (13)
H5	0.5449	0.6278	0.2345	0.067*
C6	0.3594 (5)	0.5696 (8)	0.3246 (4)	0.0440 (11)
H6	0.3362	0.4339	0.2928	0.053*
C7	0.9305 (4)	0.4031 (7)	0.8018 (3)	0.0373 (10)
C8	0.9650 (5)	0.1954 (7)	0.8420 (4)	0.0419 (10)
H8	1.0410	0.1141	0.8090	0.050*
C9	0.8885 (5)	0.1079 (8)	0.9299 (4)	0.0461 (12)
H9	0.9125	−0.0312	0.9573	0.055*
C10	0.7759 (5)	0.2293 (9)	0.9767 (4)	0.0492 (12)
C11	0.7394 (5)	0.4367 (9)	0.9407 (4)	0.0563 (13)
H11	0.6638	0.5170	0.9747	0.068*
C12	0.8179 (5)	0.5233 (8)	0.8527 (4)	0.0497 (13)
H12	0.7950	0.6641	0.8271	0.060*
C13	1.0110 (5)	0.4992 (7)	0.7031 (4)	0.0412 (12)
N1	0.1308 (4)	0.5412 (6)	0.4363 (3)	0.0401 (9)
N2	0.2128 (5)	0.9390 (7)	0.5413 (4)	0.0479 (10)
N3	0.6899 (6)	0.1334 (9)	1.0686 (4)	0.0733 (14)
O1	1.0015 (4)	0.7027 (5)	0.6879 (3)	0.0587 (10)
O2	1.0811 (3)	0.3685 (5)	0.6412 (2)	0.0456 (8)
O3	0.6015 (7)	0.2482 (10)	1.1162 (5)	0.130 (2)
O4	0.7086 (5)	−0.0577 (9)	1.0912 (4)	0.1011 (15)
H1A	0.050 (4)	0.633 (7)	0.417 (4)	0.077 (17)*
H1B	0.115 (5)	0.425 (6)	0.395 (3)	0.057 (15)*
H1C	0.133 (6)	0.497 (10)	0.509 (3)	0.081 (19)*
H2A	0.258 (6)	1.052 (11)	0.583 (5)	0.079 (18)*
H2B	0.168 (6)	0.846 (9)	0.586 (4)	0.09 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.035 (2)	0.033 (2)	0.034 (2)	−0.0012 (18)	0.0019 (17)	0.003 (2)
C2	0.035 (2)	0.034 (2)	0.039 (2)	0.002 (2)	−0.0019 (19)	0.003 (2)
C3	0.047 (3)	0.045 (3)	0.045 (3)	−0.007 (2)	−0.003 (2)	0.003 (2)
C4	0.040 (2)	0.064 (3)	0.052 (3)	−0.012 (3)	0.003 (2)	0.010 (3)
C5	0.046 (3)	0.075 (4)	0.046 (3)	0.006 (3)	0.013 (2)	0.010 (3)
C6	0.049 (2)	0.041 (3)	0.042 (3)	0.005 (2)	0.002 (2)	−0.001 (2)
C7	0.046 (2)	0.034 (3)	0.032 (2)	0.002 (2)	−0.0023 (18)	−0.004 (2)
C8	0.051 (2)	0.036 (2)	0.039 (2)	0.005 (2)	0.001 (2)	0.001 (2)
C9	0.058 (3)	0.039 (3)	0.041 (2)	0.000 (2)	0.000 (2)	0.005 (2)
C10	0.057 (3)	0.052 (3)	0.039 (3)	−0.009 (2)	0.007 (2)	0.007 (2)
C11	0.059 (3)	0.057 (3)	0.054 (3)	0.008 (3)	0.015 (2)	−0.004 (3)
C12	0.063 (3)	0.037 (3)	0.049 (3)	0.009 (2)	0.004 (3)	0.005 (2)
C13	0.048 (3)	0.042 (3)	0.034 (3)	−0.002 (2)	−0.005 (2)	0.004 (2)
N1	0.041 (2)	0.034 (2)	0.046 (2)	−0.0032 (17)	0.0037 (18)	−0.0024 (18)
N2	0.050 (2)	0.041 (2)	0.052 (3)	−0.0002 (19)	0.009 (2)	−0.014 (2)
N3	0.084 (3)	0.072 (4)	0.065 (3)	−0.001 (3)	0.030 (3)	0.008 (3)
O1	0.079 (2)	0.0380 (19)	0.060 (2)	0.0011 (17)	0.0119 (18)	0.0126 (17)
O2	0.0544 (17)	0.0425 (18)	0.0401 (17)	0.0023 (15)	0.0100 (14)	−0.0035 (16)
O3	0.169 (5)	0.105 (4)	0.120 (4)	0.008 (4)	0.099 (4)	0.012 (4)
O4	0.113 (3)	0.086 (3)	0.106 (4)	0.003 (3)	0.044 (3)	0.040 (3)

Geometric parameters (Å, º)

C1—C2	1.397 (6)	C9—H9	0.9300
C1—C6	1.367 (6)	C9—C10	1.371 (6)
C1—N1	1.466 (5)	C10—C11	1.369 (8)
C2—C3	1.388 (6)	C10—N3	1.473 (6)
C2—N2	1.391 (6)	C11—H11	0.9300
C3—H3	0.9300	C11—C12	1.379 (7)
C3—C4	1.364 (6)	C12—H12	0.9300
C4—H4	0.9300	C13—O1	1.252 (5)
C4—C5	1.385 (7)	C13—O2	1.259 (5)
C5—H5	0.9300	N1—H1A	0.93 (2)
C5—C6	1.380 (6)	N1—H1B	0.87 (2)
C6—H6	0.9300	N1—H1C	0.92 (3)
C7—C8	1.384 (6)	N2—H2A	0.93 (6)
C7—C12	1.389 (6)	N2—H2B	0.88 (3)
C7—C13	1.511 (6)	N3—O3	1.202 (7)
C8—H8	0.9300	N3—O4	1.203 (6)
C8—C9	1.372 (6)
C2—C1—N1	117.9 (3)	C10—C9—H9	120.6
C6—C1—C2	121.7 (4)	C9—C10—N3	119.0 (5)
C6—C1—N1	120.4 (4)	C11—C10—C9	122.4 (5)
C3—C2—C1	116.6 (4)	C11—C10—N3	118.5 (5)
C3—C2—N2	121.7 (4)	C10—C11—H11	120.9
N2—C2—C1	121.6 (4)	C10—C11—C12	118.2 (5)
C2—C3—H3	118.9	C12—C11—H11	120.9
C4—C3—C2	122.2 (4)	C7—C12—H12	119.5
C4—C3—H3	118.9	C11—C12—C7	120.9 (4)
C3—C4—H4	120.0	C11—C12—H12	119.5
C3—C4—C5	120.1 (4)	O1—C13—C7	117.6 (4)
C5—C4—H4	120.0	O1—C13—O2	124.7 (4)
C4—C5—H5	120.5	O2—C13—C7	117.7 (4)
C6—C5—C4	119.1 (5)	C1—N1—H1A	108 (3)
C6—C5—H5	120.5	C1—N1—H1B	112 (3)
C1—C6—C5	120.3 (4)	C1—N1—H1C	112 (3)
C1—C6—H6	119.9	H1A—N1—H1B	103 (4)
C5—C6—H6	119.9	H1A—N1—H1C	114 (5)
C8—C7—C12	118.9 (4)	H1B—N1—H1C	108 (5)
C8—C7—C13	121.3 (4)	C2—N2—H2A	114 (3)
C12—C7—C13	119.7 (4)	C2—N2—H2B	118 (4)
C7—C8—H8	119.6	H2A—N2—H2B	110 (5)
C9—C8—C7	120.8 (4)	O3—N3—C10	118.5 (6)
C9—C8—H8	119.6	O3—N3—O4	122.8 (5)
C8—C9—H9	120.6	O4—N3—C10	118.6 (5)
C10—C9—C8	118.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2^i	0.93 (2)	2.67 (5)	3.131 (5)	111 (4)
N1—H1A···N2^i	0.93 (2)	2.67 (5)	3.131 (5)	111 (4)
N1—H1A···O2^ii	0.93 (2)	1.97 (3)	2.881 (5)	166 (5)
N1—H1A···O2^ii	0.93 (2)	1.97 (3)	2.881 (5)	166 (5)
N1—H1B···O1^iii	0.87 (2)	1.96 (3)	2.787 (5)	158 (4)
N1—H1B···O1^iii	0.87 (2)	1.96 (3)	2.787 (5)	158 (4)
N1—H1C···O2^iv	0.92 (3)	1.83 (3)	2.716 (5)	162 (5)
N1—H1C···O2^iv	0.92 (3)	1.83 (3)	2.716 (5)	162 (5)
N2—H2A···O2^v	0.93 (6)	2.59 (6)	3.109 (5)	116 (4)
N2—H2A···O2^v	0.93 (6)	2.59 (6)	3.109 (5)	116 (4)
N2—H2B···O1^iv	0.88 (3)	2.13 (3)	2.966 (6)	160 (5)
N2—H2B···O1^iv	0.88 (3)	2.13 (3)	2.966 (6)	160 (5)

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

(OPDDNB)

Crystal data

C7H3N2O6·C6H9N2	F(000) = 664
Mr = 320.27	Dx = 1.527 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.9565 (10) Å	Cell parameters from 4514 reflections
b = 5.7973 (5) Å	θ = 2.5–26.0°
c = 20.2355 (16) Å	µ = 0.12 mm^−1
β = 96.805 (1)°	T = 298 K
V = 1392.8 (2) Å^3	Block
Z = 4	0.4 × 0.32 × 0.22 mm

Data collection

CCD area detector diffractometer	2255 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	Rint = 0.022
Graphite monochromator	θmax = 26.0°, θmin = 1.7°
phi and ω scans	h = −14→14
8392 measured reflections	k = −7→7
2720 independent reflections	l = −24→24

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0523P)^2 + 0.2953P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.103	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.20 e Å^−3
2720 reflections	Δρmin = −0.22 e Å^−3
229 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.025 (2)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	−0.02057 (11)	0.5918 (2)	0.11959 (7)	0.0364 (3)
C2	0.04750 (11)	0.4009 (2)	0.11379 (7)	0.0370 (3)
C3	0.14150 (13)	0.3750 (3)	0.16095 (8)	0.0468 (4)
H3	0.1883	0.2477	0.1587	0.056*
C4	0.16605 (14)	0.5350 (3)	0.21070 (8)	0.0549 (5)
H4	0.2303	0.5169	0.2410	0.066*
C5	0.09672 (15)	0.7212 (3)	0.21623 (8)	0.0561 (5)
H5	0.1131	0.8274	0.2505	0.067*
C6	0.00233 (14)	0.7495 (3)	0.17043 (8)	0.0466 (4)
H6	−0.0455	0.8742	0.1739	0.056*
C7	0.61344 (11)	1.0133 (2)	0.10335 (7)	0.0344 (3)
C8	0.50549 (11)	1.0800 (2)	0.07800 (7)	0.0350 (3)
H8	0.4939	1.2148	0.0532	0.042*
C9	0.41573 (11)	0.9441 (3)	0.09008 (7)	0.0361 (3)
C10	0.42691 (12)	0.7466 (3)	0.12818 (7)	0.0385 (3)
H10	0.3651	0.6575	0.1359	0.046*
C11	0.53474 (12)	0.6887 (2)	0.15419 (7)	0.0365 (3)
C12	0.62780 (12)	0.8150 (2)	0.14182 (7)	0.0360 (3)
H12	0.6996	0.7676	0.1591	0.043*
C13	0.71393 (12)	1.1578 (2)	0.08960 (7)	0.0373 (3)
N1	−0.11715 (10)	0.6301 (2)	0.06916 (7)	0.0376 (3)
N2	0.02375 (12)	0.2482 (2)	0.05945 (7)	0.0410 (3)
N3	0.30192 (10)	1.0163 (3)	0.06292 (6)	0.0462 (3)
N4	0.55037 (12)	0.4850 (2)	0.19748 (6)	0.0453 (3)
O1	0.69505 (9)	1.35826 (19)	0.07061 (7)	0.0556 (3)
O2	0.80852 (8)	1.06383 (19)	0.09830 (6)	0.0530 (3)
O3	0.29111 (10)	1.2025 (2)	0.03500 (7)	0.0652 (4)
O4	0.22317 (9)	0.8874 (2)	0.06994 (7)	0.0639 (4)
O5	0.64379 (11)	0.4469 (2)	0.22610 (6)	0.0678 (4)
O6	0.46814 (12)	0.3639 (2)	0.20265 (6)	0.0595 (3)
H1A	−0.1788 (14)	0.517 (3)	0.0696 (9)	0.060 (5)*
H1B	−0.1497 (15)	0.777 (3)	0.0767 (8)	0.052 (5)*
H1C	−0.0939 (16)	0.635 (3)	0.0278 (10)	0.062 (6)*
H2A	−0.0470 (17)	0.205 (3)	0.0574 (8)	0.047 (5)*
H2B	0.0661 (15)	0.122 (3)	0.0640 (9)	0.053 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0300 (7)	0.0402 (8)	0.0395 (7)	0.0008 (6)	0.0063 (6)	0.0078 (6)
C2	0.0300 (7)	0.0417 (8)	0.0402 (8)	0.0011 (6)	0.0083 (6)	0.0097 (6)
C3	0.0360 (8)	0.0558 (10)	0.0490 (9)	0.0083 (7)	0.0064 (7)	0.0132 (7)
C4	0.0446 (9)	0.0734 (12)	0.0441 (9)	−0.0006 (9)	−0.0054 (7)	0.0123 (8)
C5	0.0594 (11)	0.0641 (11)	0.0431 (9)	−0.0035 (9)	−0.0009 (8)	−0.0024 (8)
C6	0.0470 (9)	0.0464 (9)	0.0470 (9)	0.0028 (7)	0.0083 (7)	0.0010 (7)
C7	0.0307 (7)	0.0351 (7)	0.0377 (7)	0.0029 (6)	0.0057 (6)	−0.0045 (6)
C8	0.0345 (7)	0.0358 (7)	0.0355 (7)	0.0060 (6)	0.0068 (6)	0.0008 (6)
C9	0.0286 (7)	0.0442 (8)	0.0356 (7)	0.0058 (6)	0.0047 (5)	−0.0012 (6)
C10	0.0336 (7)	0.0433 (8)	0.0398 (8)	−0.0009 (6)	0.0094 (6)	−0.0008 (6)
C11	0.0408 (8)	0.0362 (7)	0.0332 (7)	0.0047 (6)	0.0074 (6)	0.0015 (6)
C12	0.0309 (7)	0.0393 (8)	0.0376 (7)	0.0067 (6)	0.0026 (6)	−0.0029 (6)
C13	0.0325 (7)	0.0360 (8)	0.0433 (8)	0.0004 (6)	0.0046 (6)	−0.0050 (6)
N1	0.0293 (6)	0.0377 (7)	0.0458 (7)	0.0045 (5)	0.0042 (5)	0.0046 (5)
N2	0.0306 (7)	0.0405 (7)	0.0524 (8)	0.0059 (6)	0.0072 (6)	0.0024 (6)
N3	0.0312 (7)	0.0600 (9)	0.0478 (7)	0.0079 (6)	0.0064 (5)	0.0058 (6)
N4	0.0552 (8)	0.0407 (7)	0.0414 (7)	0.0080 (6)	0.0114 (6)	0.0039 (5)
O1	0.0416 (6)	0.0392 (6)	0.0873 (9)	0.0018 (5)	0.0125 (6)	0.0125 (6)
O2	0.0290 (6)	0.0420 (6)	0.0880 (9)	0.0017 (5)	0.0064 (5)	0.0001 (6)
O3	0.0421 (7)	0.0733 (9)	0.0786 (9)	0.0149 (6)	0.0010 (6)	0.0304 (7)
O4	0.0301 (6)	0.0751 (9)	0.0868 (9)	−0.0008 (6)	0.0084 (6)	0.0124 (7)
O5	0.0589 (8)	0.0724 (9)	0.0708 (8)	0.0197 (7)	0.0030 (7)	0.0289 (7)
O6	0.0740 (9)	0.0467 (7)	0.0592 (7)	−0.0086 (6)	0.0137 (6)	0.0107 (5)

Geometric parameters (Å, º)

C1—C2	1.387 (2)	C9—N3	1.4668 (18)
C1—C6	1.379 (2)	C10—H10	0.9300
C1—N1	1.4645 (18)	C10—C11	1.375 (2)
C2—C3	1.394 (2)	C11—C12	1.380 (2)
C2—N2	1.414 (2)	C11—N4	1.4689 (19)
C3—H3	0.9300	C12—H12	0.9300
C3—C4	1.375 (2)	C13—O1	1.2364 (18)
C4—H4	0.9300	C13—O2	1.2488 (17)
C4—C5	1.374 (3)	N1—H1A	0.989 (14)
C5—H5	0.9300	N1—H1B	0.957 (19)
C5—C6	1.383 (2)	N1—H1C	0.91 (2)
C6—H6	0.9300	N2—H2A	0.878 (19)
C7—C8	1.3864 (19)	N2—H2B	0.890 (19)
C7—C12	1.387 (2)	N3—O3	1.2182 (18)
C7—C13	1.517 (2)	N3—O4	1.2231 (17)
C8—H8	0.9300	N4—O5	1.2160 (17)
C8—C9	1.377 (2)	N4—O6	1.2228 (18)
C9—C10	1.378 (2)
C2—C1—N1	118.94 (13)	C9—C10—H10	121.9
C6—C1—C2	121.69 (14)	C11—C10—C9	116.18 (13)
C6—C1—N1	119.34 (13)	C11—C10—H10	121.9
C1—C2—C3	117.49 (14)	C10—C11—C12	122.74 (13)
C1—C2—N2	119.97 (13)	C10—C11—N4	118.14 (13)
C3—C2—N2	122.45 (14)	C12—C11—N4	119.12 (13)
C2—C3—H3	119.5	C7—C12—H12	120.2
C4—C3—C2	120.92 (15)	C11—C12—C7	119.52 (13)
C4—C3—H3	119.5	C11—C12—H12	120.2
C3—C4—H4	119.6	O1—C13—C7	117.17 (13)
C5—C4—C3	120.75 (15)	O1—C13—O2	125.65 (14)
C5—C4—H4	119.6	O2—C13—C7	117.18 (13)
C4—C5—H5	120.3	C1—N1—H1A	114.8 (11)
C4—C5—C6	119.40 (16)	C1—N1—H1B	109.0 (10)
C6—C5—H5	120.3	C1—N1—H1C	110.1 (12)
C1—C6—C5	119.72 (15)	H1A—N1—H1B	105.9 (15)
C1—C6—H6	120.1	H1A—N1—H1C	109.6 (16)
C5—C6—H6	120.1	H1B—N1—H1C	107.1 (16)
C8—C7—C12	119.13 (13)	C2—N2—H2A	108.5 (11)
C8—C7—C13	120.05 (13)	C2—N2—H2B	112.1 (11)
C12—C7—C13	120.82 (12)	H2A—N2—H2B	107.7 (16)
C7—C8—H8	120.5	O3—N3—C9	117.99 (13)
C9—C8—C7	119.05 (13)	O3—N3—O4	123.65 (13)
C9—C8—H8	120.5	O4—N3—C9	118.36 (13)
C8—C9—C10	123.31 (13)	O5—N4—C11	118.36 (14)
C8—C9—N3	118.57 (13)	O5—N4—O6	123.86 (13)
C10—C9—N3	118.09 (13)	O6—N4—C11	117.78 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2^i	0.93	2.44	3.165 (2)	135
N1—H1A···O1^ii	0.99 (1)	1.77 (2)	2.7462 (17)	170 (2)
N1—H1B···O2^i	0.957 (19)	1.80 (2)	2.7540 (17)	171.5 (16)
N1—H1C···N2^iii	0.91 (2)	2.15 (2)	3.0341 (19)	162.0 (17)
N2—H2A···O2^ii	0.878 (19)	2.163 (19)	2.9770 (17)	153.9 (15)
N2—H2B···O4^iv	0.890 (19)	2.309 (19)	3.1598 (18)	159.9 (15)

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