Structures of three salts of phthalic acid; variation in crystal packing and geometry of the hydrogen phthalate ion

The hydrogen-bond patterns in hydrogen phthalates (HP) have been elucidated by the determination of the crystal structures of hydrogen phthalate salts of [Mg(H₂O)₄-(CH₃OH)₂]²⁺, 2-(2′-pyridylamine)pyridinium and diethylammonium. The stoichiometry of the latter salt corresponds to a hydrogen phthalate salt; however, it contains the phthalic acid in its three possible acid–base forms. The hydrogen phthalate ions in the three salts display the two common hydrogen-bonding motifs. One has a very short intramolecular O—H—O hydrogen bond (Intra-H), as seen in the magnesium salt [O...O 2.397 (2) Å]. In the other two salts the hydrogen phthalate ions are connected by hydrogen bonds into infinite chains (Chain-H) with O...O distances of 2.460 (1) Å in the diethylamine salt and 2.610 (1) Å in the 2,2′-dipyridylamine salt. This difference in hydrogen-bond pattern was further elucidated by a search in the Cambridge Structural Database for other hydrogen phthalate salts. Intra-H possesses the shortest O...O distances and an almost planar hydrogen phthalate ion, whereas the hydrogen phthalate ions show significantly more variation in the Chain-H salts. The two hydrogen-bonding motifs are reflected in the molecular geometry of the hydrogen phthalate ion.

Computing details

Data collection: KappaCCD for MgHP; Enraf-Nonius Express for deaHP; CAD-4 (Enraf-Nonius, 1989) for dpaHP. Cell refinement: DIRAX (Duisenberg, 1992) for MgHP; Enraf-Nonius Express for deaHP; CAD-4 (Enraf-Nonius, 1989) for dpaHP. Data reduction: EVALCCD (Duisenberg, 2003) for MgHP; DREADD (Blessing, 1987) for deaHP, dpaHP. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976).

Figures

(MgHP) Magnesium tetraaqua dimethanol dihydrogen phthalate

Crystal data

C2H16MgO6^2+·2(C8H5O4^−)	F(000) = 516
Mr = 490.70	Dx = 1.515 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 537 reflections
a = 9.082 (1) Å	θ = 0.8–20.4°
b = 7.8470 (7) Å	µ = 0.16 mm^−1
c = 15.1970 (8) Å	T = 122 K
β = 96.842 (5)°	Prismatic, colourless
V = 1075.32 (16) Å^3	0.45 × 0.21 × 0.18 mm
Z = 2

Data collection

KappaCCD diffractometer	1897 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
Graphite monochromator	θmax = 27.5°, θmin = 2.3°
CCD scans	h = −11→11
11508 measured reflections	k = −10→10
2464 independent reflections	l = −19→19

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) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.23	w = 1/[σ^2(Fo^2) + (0.0756P)^2 + 0.4222P] where P = (Fo^2 + 2Fc^2)/3
2464 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Mg1	0.5000	0.5000	0.5000	0.0107 (3)
O11	0.44823 (19)	0.4286 (2)	0.36894 (11)	0.0192 (4)
H11	0.404 (3)	0.347 (4)	0.3612 (19)	0.023*
C11	0.5037 (4)	0.4838 (4)	0.29106 (18)	0.0365 (8)
H11A	0.5964	0.4238	0.2846	0.044*
H11B	0.5225	0.6068	0.2947	0.044*
H11C	0.4308	0.4594	0.2397	0.044*
O12	0.71715 (18)	0.5051 (2)	0.48544 (12)	0.0147 (4)
H12A	0.754 (3)	0.432 (4)	0.4726 (19)	0.018*
H12B	0.779 (3)	0.561 (4)	0.5200 (18)	0.018*
O13	0.48678 (19)	0.7617 (2)	0.46990 (11)	0.0154 (4)
H13A	0.561 (3)	0.815 (4)	0.4628 (18)	0.018*
H13B	0.423 (3)	0.815 (4)	0.4936 (18)	0.018*
C1	1.0733 (2)	0.9767 (3)	0.36670 (13)	0.0106 (4)
C2	0.9246 (2)	0.9499 (3)	0.38400 (13)	0.0105 (4)
C3	0.8646 (2)	0.7872 (3)	0.37008 (14)	0.0137 (5)
H3	0.762 (3)	0.773 (3)	0.3809 (17)	0.016*
C4	0.9443 (3)	0.6513 (3)	0.34233 (15)	0.0153 (5)
H4	0.897 (3)	0.542 (4)	0.3323 (17)	0.018*
C5	1.0897 (3)	0.6762 (3)	0.32772 (14)	0.0154 (5)
H5	1.148 (3)	0.588 (4)	0.3074 (17)	0.018*
C6	1.1521 (2)	0.8368 (3)	0.33984 (14)	0.0129 (5)
H6	1.257 (3)	0.856 (3)	0.3291 (16)	0.015*
C7	1.1635 (2)	1.1402 (3)	0.37365 (14)	0.0122 (4)
O1	1.29007 (17)	1.1381 (2)	0.35300 (11)	0.0190 (4)
O2	1.10654 (18)	1.2794 (2)	0.40059 (11)	0.0183 (4)
H2	0.991 (3)	1.262 (3)	0.4096 (17)	0.022*
C8	0.8183 (2)	1.0778 (3)	0.41801 (14)	0.0120 (5)
O3	0.85372 (18)	1.23656 (19)	0.42136 (12)	0.0200 (4)
O4	0.70016 (17)	1.0271 (2)	0.44091 (11)	0.0177 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mg1	0.0090 (5)	0.0092 (5)	0.0142 (5)	−0.0012 (4)	0.0027 (4)	−0.0020 (4)
O11	0.0247 (9)	0.0175 (9)	0.0163 (8)	−0.0114 (7)	0.0054 (7)	−0.0032 (7)
C11	0.053 (2)	0.0405 (17)	0.0181 (13)	−0.0221 (14)	0.0129 (12)	−0.0028 (12)
O12	0.0113 (8)	0.0098 (8)	0.0233 (9)	0.0003 (6)	0.0039 (7)	−0.0043 (6)
O13	0.0110 (8)	0.0121 (8)	0.0240 (9)	−0.0014 (6)	0.0064 (7)	−0.0003 (6)
C1	0.0125 (11)	0.0108 (10)	0.0081 (10)	−0.0018 (8)	0.0001 (8)	0.0002 (8)
C2	0.0126 (11)	0.0107 (10)	0.0079 (9)	0.0002 (8)	0.0004 (8)	0.0001 (8)
C3	0.0130 (11)	0.0127 (11)	0.0156 (11)	−0.0018 (9)	0.0023 (9)	0.0011 (8)
C4	0.0189 (12)	0.0109 (10)	0.0159 (11)	−0.0032 (9)	0.0014 (9)	−0.0019 (8)
C5	0.0201 (12)	0.0109 (10)	0.0154 (11)	0.0040 (9)	0.0028 (9)	−0.0003 (9)
C6	0.0127 (11)	0.0145 (11)	0.0115 (10)	0.0002 (9)	0.0015 (8)	−0.0008 (8)
C7	0.0126 (10)	0.0120 (10)	0.0115 (10)	−0.0019 (8)	−0.0005 (8)	−0.0001 (8)
O1	0.0136 (8)	0.0175 (9)	0.0264 (9)	−0.0060 (7)	0.0055 (7)	−0.0053 (7)
O2	0.0138 (8)	0.0111 (8)	0.0304 (10)	−0.0021 (6)	0.0049 (7)	−0.0049 (7)
C8	0.0110 (10)	0.0125 (10)	0.0124 (10)	−0.0002 (9)	0.0011 (8)	−0.0008 (8)
O3	0.0160 (8)	0.0107 (8)	0.0349 (10)	−0.0008 (7)	0.0093 (7)	−0.0043 (7)
O4	0.0129 (8)	0.0157 (8)	0.0257 (9)	−0.0002 (6)	0.0078 (7)	−0.0015 (7)

Geometric parameters (Å, º)

Mg1—O12^i	2.0109 (17)	C1—C7	1.519 (3)
Mg1—O12	2.0109 (17)	C2—C3	1.394 (3)
Mg1—O11	2.0686 (16)	C2—C8	1.525 (3)
Mg1—O11^i	2.0686 (16)	C3—C4	1.383 (3)
Mg1—O13^i	2.1039 (16)	C3—H3	0.97 (3)
Mg1—O13	2.1039 (16)	C4—C5	1.379 (3)
O11—C11	1.409 (3)	C4—H4	0.96 (3)
O11—H11	0.76 (3)	C5—C6	1.385 (3)
C11—H11A	0.9800	C5—H5	0.95 (3)
C11—H11B	0.9800	C6—H6	1.00 (3)
C11—H11C	0.9800	C7—O1	1.227 (3)
O12—H12A	0.71 (3)	C7—O2	1.296 (3)
O12—H12B	0.85 (3)	O2—H2	1.08 (3)
O13—H13A	0.81 (3)	C8—O4	1.233 (3)
O13—H13B	0.83 (3)	C8—O3	1.286 (3)
C1—C6	1.398 (3)	O3—H2	1.30 (3)
C1—C2	1.422 (3)
O12^i—Mg1—O12	180.0	Mg1—O13—H13B	114.8 (19)
O12^i—Mg1—O11	89.26 (7)	H13A—O13—H13B	116 (3)
O12—Mg1—O11	90.74 (7)	C6—C1—C2	117.94 (19)
O12^i—Mg1—O11^i	90.74 (7)	C6—C1—C7	113.13 (19)
O12—Mg1—O11^i	89.26 (7)	C2—C1—C7	128.93 (19)
O11—Mg1—O11^i	180.0	C3—C2—C1	118.03 (19)
O12^i—Mg1—O13^i	89.31 (7)	C3—C2—C8	113.72 (18)
O12—Mg1—O13^i	90.69 (7)	C1—C2—C8	128.24 (19)
O11—Mg1—O13^i	86.88 (7)	C4—C3—C2	122.9 (2)
O11^i—Mg1—O13^i	93.12 (7)	C4—C3—H3	120.5 (15)
O12^i—Mg1—O13	90.69 (7)	C2—C3—H3	116.6 (15)
O12—Mg1—O13	89.31 (7)	C5—C4—C3	119.1 (2)
O11—Mg1—O13	93.12 (7)	C5—C4—H4	121.0 (16)
O11^i—Mg1—O13	86.88 (7)	C3—C4—H4	119.9 (16)
O13^i—Mg1—O13	180.00 (9)	C4—C5—C6	119.5 (2)
C11—O11—Mg1	131.49 (16)	C4—C5—H5	122.0 (16)
C11—O11—H11	111 (2)	C6—C5—H5	118.5 (16)
Mg1—O11—H11	116 (2)	C5—C6—C1	122.5 (2)
O11—C11—H11A	109.5	C5—C6—H6	120.2 (14)
O11—C11—H11B	109.5	C1—C6—H6	117.3 (14)
H11A—C11—H11B	109.5	O1—C7—O2	120.88 (19)
O11—C11—H11C	109.5	O1—C7—C1	119.01 (19)
H11A—C11—H11C	109.5	O2—C7—C1	120.11 (19)
H11B—C11—H11C	109.5	C7—O2—H2	111.2 (14)
Mg1—O12—H12A	121 (2)	O4—C8—O3	121.5 (2)
Mg1—O12—H12B	122.1 (18)	O4—C8—C2	119.41 (19)
H12A—O12—H12B	107 (3)	O3—C8—C2	119.05 (18)
Mg1—O13—H13A	120.5 (19)	C8—O3—H2	112.5 (12)

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
O11—H11···O1^ii	0.76 (3)	1.94 (3)	2.690 (2)	175 (3)
O12—H12A···O3^iii	0.71 (3)	1.99 (3)	2.686 (2)	173 (3)
O12—H12B···O2^iv	0.85 (3)	1.95 (3)	2.786 (2)	170 (3)
O13—H13A···O4	0.81 (3)	2.14 (3)	2.914 (2)	160 (3)
O13—H13B···O4^v	0.83 (3)	2.01 (3)	2.831 (2)	169 (3)
O2—H2···O3	1.08 (3)	1.30 (3)	2.378 (2)	178 (3)

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

(deaHP) Diethylammonium hydrogen phthalate

Crystal data

C8H5O4^−·C4H12N^+	F(000) = 1536
Mr = 239.27	Dx = 1.305 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 20 reflections
a = 23.289 (5) Å	θ = 38.5–45.0°
b = 10.279 (3) Å	µ = 0.81 mm^−1
c = 15.298 (2) Å	T = 122 K
β = 93.80 (2)°	Rectangular, colourless
V = 3654.0 (15) Å^3	0.52 × 0.26 × 0.24 mm
Z = 12

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.014
Radiation source: fine-focus sealed tube	θmax = 74.9°, θmin = 1.9°
Graphite monochromator	h = −29→15
ω–2θ scans	k = −5→12
13837 measured reflections	l = −19→19
7504 independent reflections	5 standard reflections every 167 min
5934 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.035	All H-atom parameters refined
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0444P)^2 + 0.8572P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
7504 reflections	Δρmax = 0.29 e Å^−3
665 parameters	Δρmin = −0.22 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: 0.00119 (7)

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1A	0.33827 (4)	0.57473 (9)	0.33686 (6)	0.01746 (19)
O2A	0.25167 (4)	0.64026 (9)	0.28169 (6)	0.0196 (2)
O3A	0.31913 (4)	0.91207 (9)	0.27363 (6)	0.0188 (2)
O4A	0.23538 (4)	1.00396 (10)	0.29985 (7)	0.0247 (2)
C1A	0.28811 (5)	0.72962 (12)	0.41711 (8)	0.0141 (2)
C2A	0.27688 (5)	0.86282 (12)	0.40759 (8)	0.0147 (3)
C3A	0.26724 (6)	0.93697 (13)	0.48177 (9)	0.0202 (3)
H3A	0.2606 (7)	1.0290 (17)	0.4730 (10)	0.026 (4)*
C4A	0.26878 (6)	0.88003 (14)	0.56413 (9)	0.0227 (3)
H4A	0.2626 (7)	0.9307 (15)	0.6159 (10)	0.024 (4)*
C5A	0.28046 (6)	0.74816 (14)	0.57376 (9)	0.0212 (3)
H5A	0.2822 (7)	0.7071 (16)	0.6334 (11)	0.028 (4)*
C6A	0.29038 (5)	0.67371 (13)	0.50033 (9)	0.0175 (3)
H6A	0.2968 (7)	0.5814 (16)	0.5070 (10)	0.025 (4)*
C7A	0.29239 (5)	0.64300 (12)	0.33806 (8)	0.0134 (2)
C8A	0.27646 (5)	0.93098 (12)	0.32004 (8)	0.0152 (3)
O1B	−0.10130 (4)	1.01514 (10)	0.30178 (6)	0.0226 (2)
O2B	−0.01684 (4)	0.92538 (9)	0.27461 (6)	0.0184 (2)
O3B	−0.06949 (4)	0.65472 (9)	0.28289 (6)	0.0183 (2)
HBB	−0.0156 (10)	1.006 (2)	0.2170 (15)	0.072 (7)*
O4B	0.01403 (4)	0.58372 (9)	0.34563 (6)	0.0202 (2)
C1B	−0.05648 (5)	0.87412 (12)	0.40858 (8)	0.0143 (2)
C2B	−0.03610 (5)	0.74642 (12)	0.41927 (8)	0.0140 (2)
C3B	−0.02732 (6)	0.69529 (13)	0.50357 (8)	0.0177 (3)
H3B	−0.0131 (6)	0.6073 (15)	0.5116 (10)	0.020 (4)*
C4B	−0.04015 (6)	0.76821 (14)	0.57651 (9)	0.0201 (3)
H4B	−0.0333 (7)	0.7298 (16)	0.6344 (11)	0.025 (4)*
C5B	−0.06188 (6)	0.89281 (13)	0.56550 (9)	0.0201 (3)
H5B	−0.0701 (7)	0.9446 (16)	0.6158 (10)	0.025 (4)*
C6B	−0.07004 (6)	0.94556 (13)	0.48197 (9)	0.0182 (3)
H6B	−0.0825 (7)	1.0341 (17)	0.4732 (10)	0.025 (4)*
C7B	−0.06021 (5)	0.94321 (12)	0.32153 (8)	0.0147 (2)
C8B	−0.03057 (5)	0.65727 (12)	0.34204 (8)	0.0138 (2)
O1C	0.32337 (4)	0.08025 (9)	0.14850 (6)	0.0203 (2)
HAC	0.3210 (9)	0.022 (2)	0.2006 (15)	0.067 (7)*
O2C	0.40082 (4)	0.16156 (9)	0.22469 (6)	0.0205 (2)
O3C	0.34660 (4)	0.42377 (9)	0.21248 (6)	0.0195 (2)
HCA	0.3427 (10)	0.497 (2)	0.2679 (16)	0.079 (8)*
O4C	0.42696 (4)	0.53433 (9)	0.18920 (6)	0.0216 (2)
C1C	0.37849 (5)	0.23946 (12)	0.08014 (8)	0.0144 (2)
C2C	0.39594 (5)	0.36947 (12)	0.08772 (8)	0.0152 (3)
C3C	0.41431 (6)	0.43414 (13)	0.01416 (9)	0.0215 (3)
H3C	0.4258 (7)	0.5255 (17)	0.0203 (11)	0.026 (4)*
C4C	0.41424 (7)	0.37145 (15)	−0.06627 (9)	0.0248 (3)
H4C	0.4265 (7)	0.4164 (16)	−0.1169 (11)	0.030 (4)*
C5C	0.39570 (6)	0.24379 (14)	−0.07418 (9)	0.0209 (3)
H5C	0.3954 (7)	0.2003 (16)	−0.1301 (11)	0.026 (4)*
C6C	0.37817 (6)	0.17759 (13)	−0.00118 (8)	0.0177 (3)
H6C	0.3670 (7)	0.0875 (16)	−0.0060 (10)	0.024 (4)*
C7C	0.36830 (5)	0.15898 (12)	0.15958 (8)	0.0147 (3)
C8C	0.39140 (5)	0.44886 (12)	0.16950 (8)	0.0151 (3)
N1	0.18476 (5)	1.22274 (11)	0.22998 (7)	0.0182 (2)
H1NA	0.1462 (8)	1.2005 (17)	0.2162 (11)	0.032 (5)*
H1NB	0.2063 (7)	1.1471 (18)	0.2408 (11)	0.034 (5)*
C11	0.19732 (7)	1.21744 (18)	0.07157 (10)	0.0289 (3)
H11A	0.1557 (8)	1.1974 (17)	0.0579 (11)	0.033 (5)*
H11B	0.2118 (8)	1.2685 (19)	0.0233 (13)	0.046 (6)*
H11C	0.2183 (7)	1.1338 (18)	0.0786 (11)	0.034 (5)*
C12	0.18862 (6)	1.29553 (17)	0.31479 (9)	0.0263 (3)
H12A	0.1700 (8)	1.3789 (18)	0.3032 (11)	0.035 (5)*
H12B	0.1648 (8)	1.2500 (19)	0.3552 (12)	0.044 (5)*
C13	0.20689 (6)	1.29532 (14)	0.15485 (9)	0.0197 (3)
H13A	0.2478 (7)	1.3082 (15)	0.1693 (10)	0.023 (4)*
H13B	0.1859 (6)	1.3785 (15)	0.1509 (9)	0.017 (4)*
C14	0.24984 (7)	1.31110 (16)	0.35102 (10)	0.0251 (3)
H14A	0.2716 (9)	1.360 (2)	0.3080 (14)	0.061 (6)*
H14B	0.2696 (8)	1.227 (2)	0.3629 (13)	0.048 (6)*
H14C	0.2520 (7)	1.3594 (18)	0.4079 (12)	0.037 (5)*
N2	0.42198 (5)	0.77189 (11)	0.28422 (7)	0.0176 (2)
H2NA	0.4170 (7)	0.6889 (17)	0.2611 (11)	0.029 (4)*
H2NB	0.3889 (8)	0.8170 (17)	0.2799 (11)	0.031 (5)*
C21	0.47708 (6)	0.63622 (16)	0.39409 (10)	0.0259 (3)
H21A	0.4960 (7)	0.6374 (17)	0.4540 (11)	0.032 (5)*
H21B	0.4523 (7)	0.5609 (16)	0.3875 (10)	0.026 (4)*
H21C	0.5085 (7)	0.6312 (16)	0.3529 (11)	0.029 (4)*
C22	0.44354 (6)	0.76052 (15)	0.37845 (9)	0.0222 (3)
H22A	0.4672 (7)	0.8373 (16)	0.3917 (10)	0.023 (4)*
H22B	0.4110 (7)	0.7632 (16)	0.4126 (10)	0.023 (4)*
C23	0.46347 (6)	0.83667 (15)	0.22784 (10)	0.0235 (3)
H23A	0.4698 (7)	0.9248 (16)	0.2515 (10)	0.023 (4)*
H23B	0.4996 (7)	0.7880 (16)	0.2365 (10)	0.026 (4)*
C24	0.44026 (7)	0.83816 (16)	0.13321 (10)	0.0288 (3)
H24A	0.4688 (8)	0.8845 (18)	0.0979 (11)	0.037 (5)*
H24B	0.4030 (8)	0.8838 (19)	0.1246 (12)	0.042 (5)*
H24C	0.4363 (8)	0.7507 (19)	0.1097 (11)	0.036 (5)*
N3	0.13885 (5)	0.70835 (11)	0.31735 (8)	0.0187 (2)
H3NA	0.1165 (7)	0.6459 (17)	0.2888 (11)	0.030 (4)*
H3NB	0.1779 (7)	0.6941 (16)	0.3060 (10)	0.026 (4)*
C31	0.14500 (7)	0.56699 (16)	0.44805 (10)	0.0288 (3)
H31A	0.1158 (8)	0.5052 (18)	0.4228 (12)	0.038 (5)*
H31B	0.1850 (8)	0.5364 (18)	0.4352 (12)	0.041 (5)*
H31C	0.1429 (8)	0.5646 (19)	0.5117 (13)	0.044 (5)*
C32	0.13360 (6)	0.70299 (15)	0.41402 (9)	0.0231 (3)
H32A	0.1605 (7)	0.7684 (16)	0.4396 (10)	0.026 (4)*
H32B	0.0948 (7)	0.7327 (15)	0.4229 (10)	0.021 (4)*
C33	0.11872 (6)	0.83448 (14)	0.27785 (11)	0.0251 (3)
H33A	0.0779 (7)	0.8407 (16)	0.2886 (10)	0.030 (4)*
H33B	0.1413 (7)	0.9003 (16)	0.3089 (10)	0.026 (4)*
C34	0.12631 (9)	0.83741 (17)	0.18079 (12)	0.0359 (4)
H34A	0.1674 (8)	0.8269 (18)	0.1693 (12)	0.040 (5)*
H34B	0.1035 (8)	0.767 (2)	0.1521 (13)	0.046 (6)*
H34C	0.1128 (9)	0.921 (2)	0.1564 (13)	0.053 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0153 (4)	0.0174 (4)	0.0200 (5)	0.0025 (4)	0.0027 (3)	−0.0040 (4)
O2A	0.0194 (5)	0.0230 (5)	0.0162 (5)	0.0039 (4)	−0.0011 (4)	−0.0033 (4)
O3A	0.0197 (5)	0.0189 (5)	0.0184 (5)	0.0011 (4)	0.0054 (4)	0.0048 (4)
O4A	0.0239 (5)	0.0238 (5)	0.0269 (5)	0.0077 (4)	0.0042 (4)	0.0083 (4)
C1A	0.0123 (5)	0.0160 (6)	0.0139 (6)	0.0001 (5)	0.0015 (4)	−0.0007 (5)
C2A	0.0136 (6)	0.0152 (6)	0.0154 (6)	−0.0007 (5)	0.0015 (5)	−0.0002 (5)
C3A	0.0245 (7)	0.0152 (6)	0.0211 (7)	0.0009 (5)	0.0034 (5)	−0.0031 (5)
C4A	0.0273 (7)	0.0255 (7)	0.0157 (6)	0.0002 (6)	0.0030 (5)	−0.0078 (6)
C5A	0.0228 (7)	0.0279 (7)	0.0130 (6)	0.0026 (6)	0.0014 (5)	0.0012 (5)
C6A	0.0173 (6)	0.0183 (6)	0.0169 (6)	0.0031 (5)	0.0009 (5)	0.0019 (5)
C7A	0.0150 (6)	0.0114 (5)	0.0144 (6)	−0.0015 (5)	0.0041 (5)	0.0020 (5)
C8A	0.0168 (6)	0.0116 (6)	0.0171 (6)	−0.0021 (5)	0.0006 (5)	0.0002 (5)
O1B	0.0208 (5)	0.0245 (5)	0.0227 (5)	0.0068 (4)	0.0033 (4)	0.0083 (4)
O2B	0.0191 (4)	0.0186 (5)	0.0180 (5)	0.0015 (4)	0.0043 (4)	0.0051 (4)
O3B	0.0182 (4)	0.0207 (5)	0.0158 (4)	0.0021 (4)	−0.0010 (3)	−0.0029 (4)
O4B	0.0195 (5)	0.0224 (5)	0.0185 (5)	0.0070 (4)	−0.0015 (4)	−0.0067 (4)
C1B	0.0138 (6)	0.0144 (6)	0.0146 (6)	−0.0012 (5)	0.0006 (4)	0.0003 (5)
C2B	0.0129 (5)	0.0153 (6)	0.0137 (6)	−0.0001 (5)	0.0014 (4)	−0.0006 (5)
C3B	0.0202 (6)	0.0166 (6)	0.0163 (6)	0.0027 (5)	0.0002 (5)	0.0016 (5)
C4B	0.0236 (7)	0.0234 (7)	0.0132 (6)	−0.0006 (5)	0.0013 (5)	0.0019 (5)
C5B	0.0238 (7)	0.0217 (7)	0.0152 (6)	−0.0005 (5)	0.0037 (5)	−0.0057 (5)
C6B	0.0210 (6)	0.0141 (6)	0.0197 (7)	0.0007 (5)	0.0022 (5)	−0.0019 (5)
C7B	0.0158 (6)	0.0124 (6)	0.0157 (6)	−0.0019 (5)	−0.0003 (5)	−0.0004 (5)
C8B	0.0159 (6)	0.0123 (6)	0.0136 (6)	−0.0015 (5)	0.0027 (5)	0.0010 (5)
O1C	0.0212 (5)	0.0199 (5)	0.0196 (5)	−0.0066 (4)	−0.0003 (4)	0.0050 (4)
O2C	0.0238 (5)	0.0232 (5)	0.0143 (4)	−0.0026 (4)	−0.0012 (4)	0.0020 (4)
O3C	0.0204 (5)	0.0183 (5)	0.0207 (5)	−0.0024 (4)	0.0075 (4)	−0.0053 (4)
O4C	0.0232 (5)	0.0205 (5)	0.0216 (5)	−0.0059 (4)	0.0050 (4)	−0.0054 (4)
C1C	0.0129 (6)	0.0164 (6)	0.0138 (6)	0.0009 (5)	0.0004 (4)	0.0007 (5)
C2C	0.0152 (6)	0.0160 (6)	0.0143 (6)	0.0005 (5)	0.0006 (5)	0.0006 (5)
C3C	0.0301 (7)	0.0166 (6)	0.0178 (7)	−0.0041 (6)	0.0028 (5)	0.0017 (5)
C4C	0.0348 (8)	0.0253 (7)	0.0147 (7)	−0.0050 (6)	0.0051 (6)	0.0040 (6)
C5C	0.0255 (7)	0.0246 (7)	0.0126 (6)	−0.0020 (6)	0.0011 (5)	−0.0027 (5)
C6C	0.0202 (6)	0.0167 (6)	0.0160 (6)	−0.0025 (5)	0.0006 (5)	−0.0008 (5)
C7C	0.0172 (6)	0.0124 (6)	0.0150 (6)	0.0016 (5)	0.0040 (5)	−0.0016 (5)
C8C	0.0176 (6)	0.0120 (6)	0.0154 (6)	0.0015 (5)	−0.0002 (5)	0.0018 (5)
N1	0.0158 (5)	0.0191 (6)	0.0194 (6)	0.0006 (4)	0.0008 (4)	0.0027 (5)
C11	0.0267 (8)	0.0396 (9)	0.0204 (7)	0.0018 (7)	0.0019 (6)	−0.0058 (7)
C12	0.0241 (7)	0.0378 (9)	0.0171 (7)	0.0048 (6)	0.0020 (5)	−0.0014 (6)
C13	0.0190 (6)	0.0214 (7)	0.0189 (7)	−0.0003 (5)	0.0029 (5)	0.0012 (5)
C14	0.0273 (7)	0.0264 (8)	0.0216 (7)	−0.0086 (6)	0.0014 (6)	−0.0015 (6)
N2	0.0164 (5)	0.0160 (6)	0.0204 (6)	−0.0004 (4)	0.0015 (4)	−0.0024 (4)
C21	0.0199 (7)	0.0356 (9)	0.0220 (7)	0.0019 (6)	0.0000 (6)	0.0030 (6)
C22	0.0190 (7)	0.0284 (8)	0.0193 (7)	−0.0005 (6)	0.0013 (5)	−0.0070 (6)
C23	0.0196 (7)	0.0235 (7)	0.0279 (7)	−0.0046 (6)	0.0048 (6)	−0.0002 (6)
C24	0.0367 (9)	0.0235 (8)	0.0267 (8)	−0.0041 (7)	0.0070 (6)	0.0001 (6)
N3	0.0159 (5)	0.0174 (6)	0.0224 (6)	0.0002 (4)	−0.0005 (4)	−0.0062 (5)
C31	0.0317 (8)	0.0326 (8)	0.0219 (7)	−0.0019 (7)	0.0004 (6)	−0.0002 (6)
C32	0.0196 (7)	0.0270 (7)	0.0230 (7)	−0.0016 (6)	0.0030 (5)	−0.0089 (6)
C33	0.0214 (7)	0.0172 (7)	0.0371 (8)	0.0029 (6)	0.0047 (6)	−0.0009 (6)
C34	0.0448 (10)	0.0268 (8)	0.0361 (9)	0.0087 (8)	0.0018 (8)	0.0048 (7)

Geometric parameters (Å, º)

O1A—C7A	1.2795 (15)	C5C—H5C	0.965 (16)
O1A—HCA	1.33 (2)	C6C—H6C	0.964 (17)
O2A—C7A	1.2390 (15)	N1—C13	1.4906 (17)
O3A—C8A	1.2739 (15)	N1—C12	1.4952 (18)
O4A—C8A	1.2387 (16)	N1—H1NA	0.937 (18)
C1A—C6A	1.3946 (18)	N1—H1NB	0.933 (18)
C1A—C2A	1.3997 (17)	C11—C13	1.509 (2)
C1A—C7A	1.5103 (17)	C11—H11A	0.999 (18)
C2A—C3A	1.3975 (18)	C11—H11B	0.98 (2)
C2A—C8A	1.5109 (17)	C11—H11C	0.991 (19)
C3A—C4A	1.3875 (19)	C12—C14	1.504 (2)
C3A—H3A	0.967 (17)	C12—H12A	0.972 (18)
C4A—C5A	1.388 (2)	C12—H12B	0.977 (19)
C4A—H4A	0.966 (16)	C13—H13A	0.972 (16)
C5A—C6A	1.3911 (19)	C13—H13B	0.985 (15)
C5A—H5A	1.004 (16)	C14—H14A	0.99 (2)
C6A—H6A	0.965 (17)	C14—H14B	0.99 (2)
O1B—C7B	1.2310 (15)	C14—H14C	1.000 (18)
O2B—C7B	1.2903 (15)	N2—C23	1.4936 (17)
O2B—HBB	1.21 (2)	N2—C22	1.4992 (17)
O3B—C8B	1.2378 (15)	N2—H2NA	0.928 (18)
O4B—C8B	1.2829 (15)	N2—H2NB	0.898 (18)
C1B—C6B	1.3952 (18)	C21—C22	1.508 (2)
C1B—C2B	1.4016 (17)	C21—H21A	0.991 (17)
C1B—C7B	1.5066 (17)	C21—H21B	0.966 (17)
C2B—C3B	1.3951 (17)	C21—H21C	0.998 (17)
C2B—C8B	1.5074 (17)	C22—H22A	0.976 (16)
C3B—C4B	1.3930 (18)	C22—H22B	0.948 (16)
C3B—H3B	0.968 (16)	C23—C24	1.511 (2)
C4B—C5B	1.3833 (19)	C23—H23A	0.983 (16)
C4B—H4B	0.972 (16)	C23—H23B	0.980 (17)
C5B—C6B	1.3895 (19)	C24—H24A	1.004 (18)
C5B—H5B	0.965 (16)	C24—H24B	0.988 (19)
C6B—H6B	0.962 (17)	C24—H24C	0.970 (19)
O1C—C7C	1.3248 (15)	N3—C33	1.4926 (18)
O1C—HAC	1.00 (2)	N3—C32	1.4931 (18)
O2C—C7C	1.2109 (15)	N3—H3NA	0.918 (18)
O3C—C8C	1.2955 (15)	N3—H3NB	0.948 (17)
O3C—HCA	1.14 (2)	C31—C32	1.509 (2)
O4C—C8C	1.2311 (15)	C31—H31A	0.989 (19)
C1C—C6C	1.3966 (17)	C31—H31B	1.014 (19)
C1C—C2C	1.3994 (17)	C31—H31C	0.978 (19)
C1C—C7C	1.5020 (17)	C32—H32A	0.982 (17)
C2C—C3C	1.3981 (18)	C32—H32B	0.971 (16)
C2C—C8C	1.5034 (17)	C33—C34	1.507 (2)
C3C—C4C	1.3889 (19)	C33—H33A	0.978 (17)
C3C—H3C	0.979 (17)	C33—H33B	0.962 (17)
C4C—C5C	1.384 (2)	C34—H34A	0.989 (19)
C4C—H4C	0.962 (17)	C34—H34B	0.98 (2)
C5C—C6C	1.3919 (18)	C34—H34C	0.98 (2)
C7A—O1A—HCA	116.6 (10)	C13—C11—H11B	108.2 (11)
C6A—C1A—C2A	119.58 (12)	H11A—C11—H11B	109.2 (15)
C6A—C1A—C7A	119.17 (11)	C13—C11—H11C	108.9 (10)
C2A—C1A—C7A	121.00 (11)	H11A—C11—H11C	107.9 (14)
C3A—C2A—C1A	119.20 (12)	H11B—C11—H11C	110.7 (15)
C3A—C2A—C8A	118.36 (11)	N1—C12—C14	111.97 (12)
C1A—C2A—C8A	122.41 (11)	N1—C12—H12A	106.4 (10)
C4A—C3A—C2A	120.77 (13)	C14—C12—H12A	112.0 (11)
C4A—C3A—H3A	122.3 (10)	N1—C12—H12B	107.8 (11)
C2A—C3A—H3A	116.9 (10)	C14—C12—H12B	112.5 (11)
C3A—C4A—C5A	120.08 (13)	H12A—C12—H12B	105.8 (15)
C3A—C4A—H4A	121.3 (9)	N1—C13—C11	110.26 (12)
C5A—C4A—H4A	118.6 (9)	N1—C13—H13A	106.1 (9)
C4A—C5A—C6A	119.56 (13)	C11—C13—H13A	110.6 (9)
C4A—C5A—H5A	120.2 (9)	N1—C13—H13B	106.6 (9)
C6A—C5A—H5A	120.3 (9)	C11—C13—H13B	111.4 (9)
C5A—C6A—C1A	120.81 (12)	H13A—C13—H13B	111.7 (13)
C5A—C6A—H6A	119.2 (9)	C12—C14—H14A	108.8 (12)
C1A—C6A—H6A	119.9 (9)	C12—C14—H14B	112.9 (11)
O2A—C7A—O1A	125.37 (12)	H14A—C14—H14B	108.3 (17)
O2A—C7A—C1A	118.86 (11)	C12—C14—H14C	111.4 (10)
O1A—C7A—C1A	115.74 (11)	H14A—C14—H14C	109.0 (16)
O4A—C8A—O3A	124.86 (12)	H14B—C14—H14C	106.2 (15)
O4A—C8A—C2A	117.48 (11)	C23—N2—C22	113.69 (11)
O3A—C8A—C2A	117.63 (11)	C23—N2—H2NA	105.1 (10)
C7B—O2B—HBB	111.4 (11)	C22—N2—H2NA	108.7 (10)
C6B—C1B—C2B	119.46 (12)	C23—N2—H2NB	108.2 (11)
C6B—C1B—C7B	117.41 (11)	C22—N2—H2NB	110.0 (11)
C2B—C1B—C7B	122.94 (11)	H2NA—N2—H2NB	111.1 (15)
C3B—C2B—C1B	119.24 (11)	C22—C21—H21A	109.3 (10)
C3B—C2B—C8B	118.72 (11)	C22—C21—H21B	111.3 (10)
C1B—C2B—C8B	121.58 (11)	H21A—C21—H21B	109.5 (14)
C4B—C3B—C2B	120.78 (12)	C22—C21—H21C	109.7 (10)
C4B—C3B—H3B	119.4 (9)	H21A—C21—H21C	106.5 (13)
C2B—C3B—H3B	119.8 (9)	H21B—C21—H21C	110.4 (13)
C5B—C4B—C3B	119.79 (12)	N2—C22—C21	110.82 (11)
C5B—C4B—H4B	121.5 (10)	N2—C22—H22A	106.6 (9)
C3B—C4B—H4B	118.7 (10)	C21—C22—H22A	111.8 (9)
C4B—C5B—C6B	119.99 (12)	N2—C22—H22B	107.4 (10)
C4B—C5B—H5B	120.2 (10)	C21—C22—H22B	111.2 (10)
C6B—C5B—H5B	119.7 (10)	H22A—C22—H22B	108.8 (13)
C5B—C6B—C1B	120.68 (12)	N2—C23—C24	110.71 (12)
C5B—C6B—H6B	121.3 (10)	N2—C23—H23A	106.6 (9)
C1B—C6B—H6B	117.9 (10)	C24—C23—H23A	112.3 (9)
O1B—C7B—O2B	124.98 (12)	N2—C23—H23B	106.1 (10)
O1B—C7B—C1B	119.89 (11)	C24—C23—H23B	112.6 (10)
O2B—C7B—C1B	115.04 (11)	H23A—C23—H23B	108.3 (13)
O3B—C8B—O4B	124.77 (11)	C23—C24—H24A	108.2 (10)
O3B—C8B—C2B	119.30 (11)	C23—C24—H24B	112.8 (11)
O4B—C8B—C2B	115.83 (11)	H24A—C24—H24B	108.1 (15)
C7C—O1C—HAC	110.2 (13)	C23—C24—H24C	111.4 (11)
C8C—O3C—HCA	110.5 (12)	H24A—C24—H24C	106.9 (14)
C6C—C1C—C2C	119.54 (12)	H24B—C24—H24C	109.2 (15)
C6C—C1C—C7C	118.56 (11)	C33—N3—C32	112.89 (11)
C2C—C1C—C7C	121.30 (11)	C33—N3—H3NA	105.2 (11)
C3C—C2C—C1C	119.34 (12)	C32—N3—H3NA	111.4 (10)
C3C—C2C—C8C	116.99 (11)	C33—N3—H3NB	109.8 (10)
C1C—C2C—C8C	123.45 (11)	C32—N3—H3NB	108.5 (10)
C4C—C3C—C2C	120.66 (13)	H3NA—N3—H3NB	108.9 (14)
C4C—C3C—H3C	121.0 (10)	C32—C31—H31A	111.0 (11)
C2C—C3C—H3C	118.3 (10)	C32—C31—H31B	111.3 (11)
C5C—C4C—C3C	119.95 (13)	H31A—C31—H31B	109.9 (15)
C5C—C4C—H4C	119.5 (10)	C32—C31—H31C	110.3 (12)
C3C—C4C—H4C	120.5 (10)	H31A—C31—H31C	107.1 (15)
C4C—C5C—C6C	119.98 (13)	H31B—C31—H31C	107.0 (15)
C4C—C5C—H5C	120.0 (10)	N3—C32—C31	110.60 (12)
C6C—C5C—H5C	120.0 (10)	N3—C32—H32A	106.1 (9)
C5C—C6C—C1C	120.49 (12)	C31—C32—H32A	113.8 (10)
C5C—C6C—H6C	120.1 (9)	N3—C32—H32B	105.4 (9)
C1C—C6C—H6C	119.4 (9)	C31—C32—H32B	112.7 (9)
O2C—C7C—O1C	124.35 (12)	H32A—C32—H32B	107.6 (13)
O2C—C7C—C1C	121.99 (11)	N3—C33—C34	111.22 (12)
O1C—C7C—C1C	113.50 (11)	N3—C33—H33A	105.8 (10)
O4C—C8C—O3C	124.70 (12)	C34—C33—H33A	110.0 (10)
O4C—C8C—C2C	120.51 (11)	N3—C33—H33B	105.3 (10)
O3C—C8C—C2C	114.70 (11)	C34—C33—H33B	112.1 (10)
C13—N1—C12	114.50 (11)	H33A—C33—H33B	112.1 (13)
C13—N1—H1NA	108.9 (10)	C33—C34—H34A	110.5 (11)
C12—N1—H1NA	108.6 (10)	C33—C34—H34B	109.3 (12)
C13—N1—H1NB	110.1 (11)	H34A—C34—H34B	109.9 (16)
C12—N1—H1NB	105.2 (11)	C33—C34—H34C	109.6 (12)
H1NA—N1—H1NB	109.4 (15)	H34A—C34—H34C	108.5 (16)
C13—C11—H11A	111.9 (10)	H34B—C34—H34C	109.0 (16)
C6A—C1A—C2A—C3A	−1.02 (18)	C6B—C1B—C7B—O2B	133.62 (12)
C7A—C1A—C2A—C3A	173.30 (11)	C2B—C1B—C7B—O2B	−41.47 (17)
C6A—C1A—C2A—C8A	177.17 (11)	C3B—C2B—C8B—O3B	129.65 (13)
C7A—C1A—C2A—C8A	−8.52 (18)	C1B—C2B—C8B—O3B	−42.51 (17)
C1A—C2A—C3A—C4A	0.1 (2)	C3B—C2B—C8B—O4B	−46.88 (16)
C8A—C2A—C3A—C4A	−178.15 (12)	C1B—C2B—C8B—O4B	140.95 (12)
C2A—C3A—C4A—C5A	0.5 (2)	C6C—C1C—C2C—C3C	−1.78 (18)
C3A—C4A—C5A—C6A	−0.2 (2)	C7C—C1C—C2C—C3C	169.22 (12)
C4A—C5A—C6A—C1A	−0.7 (2)	C6C—C1C—C2C—C8C	172.76 (12)
C2A—C1A—C6A—C5A	1.33 (19)	C7C—C1C—C2C—C8C	−16.24 (18)
C7A—C1A—C6A—C5A	−173.09 (12)	C1C—C2C—C3C—C4C	1.3 (2)
C6A—C1A—C7A—O2A	119.08 (13)	C8C—C2C—C3C—C4C	−173.57 (13)
C2A—C1A—C7A—O2A	−55.26 (16)	C2C—C3C—C4C—C5C	0.2 (2)
C6A—C1A—C7A—O1A	−58.94 (15)	C3C—C4C—C5C—C6C	−1.2 (2)
C2A—C1A—C7A—O1A	126.72 (12)	C4C—C5C—C6C—C1C	0.7 (2)
C3A—C2A—C8A—O4A	−49.21 (17)	C2C—C1C—C6C—C5C	0.78 (19)
C1A—C2A—C8A—O4A	132.59 (13)	C7C—C1C—C6C—C5C	−170.46 (12)
C3A—C2A—C8A—O3A	128.83 (13)	C6C—C1C—C7C—O2C	127.69 (14)
C1A—C2A—C8A—O3A	−49.37 (17)	C2C—C1C—C7C—O2C	−43.39 (18)
C6B—C1B—C2B—C3B	−2.87 (18)	C6C—C1C—C7C—O1C	−47.86 (15)
C7B—C1B—C2B—C3B	172.12 (12)	C2C—C1C—C7C—O1C	141.05 (12)
C6B—C1B—C2B—C8B	169.25 (11)	C3C—C2C—C8C—O4C	−37.45 (18)
C7B—C1B—C2B—C8B	−15.75 (18)	C1C—C2C—C8C—O4C	147.89 (13)
C1B—C2B—C3B—C4B	1.89 (19)	C3C—C2C—C8C—O3C	139.23 (12)
C8B—C2B—C3B—C4B	−170.46 (12)	C1C—C2C—C8C—O3C	−35.42 (17)
C2B—C3B—C4B—C5B	0.0 (2)	C13—N1—C12—C14	−69.76 (16)
C3B—C4B—C5B—C6B	−1.0 (2)	C12—N1—C13—C11	−176.10 (12)
C4B—C5B—C6B—C1B	0.0 (2)	C23—N2—C22—C21	−88.55 (15)
C2B—C1B—C6B—C5B	1.98 (19)	C22—N2—C23—C24	176.94 (12)
C7B—C1B—C6B—C5B	−173.29 (12)	C33—N3—C32—C31	170.58 (12)
C6B—C1B—C7B—O1B	−43.11 (17)	C32—N3—C33—C34	178.37 (13)
C2B—C1B—C7B—O1B	141.80 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2B—HBB···O4B^i	1.21 (2)	1.25 (2)	2.4603 (12)	176 (2)
O3C—HCA···O1A	1.14 (2)	1.33 (2)	2.4728 (12)	175 (2)
O1C—HAC···O3A^ii	1.00 (2)	1.59 (2)	2.5861 (13)	171 (2)
N1—H1NA···O3B^i	0.937 (18)	1.849 (18)	2.7685 (14)	166.6 (15)
N1—H1NB···O4A	0.933 (18)	1.833 (19)	2.7243 (15)	158.8 (16)
N2—H2NA···O4C	0.928 (18)	1.955 (18)	2.8481 (15)	160.9 (15)
N2—H2NB···O3A	0.898 (18)	1.893 (18)	2.7907 (15)	178.7 (16)
N3—H3NA···O1B^iii	0.918 (18)	1.946 (18)	2.7962 (15)	153.2 (15)
N3—H3NB···O2A	0.948 (17)	1.866 (17)	2.8075 (14)	171.5 (15)

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

(dpaHP) 2-(2'-pyridylamino)-pyridinium hydrogen phthalate

Crystal data

C10H10N3^+·C8H5O4^−	F(000) = 704
Mr = 337.33	Dx = 1.425 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.179 (3) Å	θ = 20.2–22.0°
b = 9.0034 (17) Å	µ = 0.10 mm^−1
c = 24.610 (4) Å	T = 122 K
β = 98.76 (2)°	Prismatic, colourless
V = 1572.2 (7) Å^3	0.52 × 0.32 × 0.14 mm
Z = 4

Data collection

Enraf-Nonoius CAD-4 diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 45.0°, θmin = 1.7°
Graphite monochromator	h = −14→14
ω –2θ scans	k = 0→17
20676 measured reflections	l = 0→48
12908 independent reflections	5 standard reflections every 167 min
10136 reflections with I > 2σ(I)	intensity decay: 3%

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 0.4582P] where P = (Fo^2 + 2Fc^2)/3
12908 reflections	(Δ/σ)max = 0.022
362 parameters	Δρmax = 0.69 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	1.22244 (9)	0.89348 (7)	0.19221 (2)	0.01243 (8)
C2	1.02802 (8)	0.88672 (7)	0.17403 (2)	0.01170 (8)
C3	0.90705 (10)	0.96698 (8)	0.20239 (3)	0.01555 (10)
H3	0.7742 (19)	0.9679 (15)	0.1901 (6)	0.019*
C4	0.97722 (11)	1.05428 (9)	0.24764 (3)	0.01973 (12)
H4	0.890 (2)	1.1092 (16)	0.2664 (6)	0.024*
C5	1.17061 (12)	1.06238 (9)	0.26497 (3)	0.02031 (12)
H5	1.225 (2)	1.1241 (17)	0.2963 (6)	0.024*
C6	1.29291 (10)	0.98174 (9)	0.23743 (3)	0.01748 (11)
H6	1.425 (2)	0.9846 (16)	0.2506 (6)	0.021*
C7	1.36390 (9)	0.80254 (7)	0.16751 (3)	0.01325 (9)
O1	1.39024 (9)	0.67131 (6)	0.17712 (3)	0.02141 (11)
O2	1.46968 (8)	0.88465 (6)	0.13951 (3)	0.01846 (9)
H0	1.568 (2)	0.8358 (17)	0.1323 (6)	0.022*
C8	0.95372 (8)	0.79966 (7)	0.12287 (2)	0.01214 (8)
O3	1.06929 (8)	0.76157 (8)	0.09280 (2)	0.02288 (12)
O4	0.77759 (7)	0.77121 (6)	0.11261 (2)	0.01672 (9)
N1	0.25318 (10)	0.42626 (8)	−0.02611 (3)	0.01463 (12)	0.843 (2)
H1	0.246 (2)	0.3619 (18)	−0.0530 (7)	0.018*	0.843 (2)
C11	0.29114 (11)	0.57351 (10)	−0.03770 (4)	0.01375 (12)	0.843 (2)
N12	0.28797 (12)	0.67393 (9)	0.00184 (4)	0.01681 (13)	0.843 (2)
C13	0.3203 (3)	0.81567 (17)	−0.00950 (7)	0.0217 (3)	0.843 (2)
H13	0.3184	0.8874	0.0187	0.026*	0.843 (2)
C14	0.3566 (7)	0.8635 (5)	−0.0606 (2)	0.0227 (3)	0.843 (2)
H14	0.3761	0.9659	−0.0671	0.027*	0.843 (2)
C15	0.3641 (6)	0.7570 (3)	−0.10291 (17)	0.0238 (5)	0.843 (2)
H15	0.3903	0.7851	−0.1382	0.029*	0.843 (2)
C16	0.3313 (3)	0.6096 (3)	−0.09016 (7)	0.0199 (3)	0.843 (2)
H16	0.3361	0.5340	−0.1168	0.024*	0.843 (2)
C21	0.21165 (11)	0.37095 (10)	0.02190 (4)	0.01305 (12)	0.843 (2)
N22	0.19948 (11)	0.45959 (8)	0.06539 (4)	0.01516 (12)	0.843 (2)
C23	0.16516 (17)	0.40565 (12)	0.11431 (5)	0.01927 (17)	0.843 (2)
H23	0.1583	0.4720	0.1440	0.023*	0.843 (2)
C24	0.1402 (3)	0.2559 (2)	0.12144 (6)	0.0203 (2)	0.843 (2)
H24	0.1196	0.2179	0.1560	0.024*	0.843 (2)
C25	0.1458 (4)	0.1605 (2)	0.07679 (10)	0.0195 (3)	0.843 (2)
H25	0.1254	0.0570	0.0806	0.023*	0.843 (2)
C26	0.18109 (19)	0.21698 (13)	0.02730 (5)	0.01677 (17)	0.843 (2)
H26	0.1848	0.1526	−0.0031	0.020*	0.843 (2)
N1'	0.2381 (6)	0.5790 (5)	0.03425 (18)	0.0190 (7)	0.157 (2)
H1'	0.2265	0.6433	0.0604	0.023*	0.157 (2)
C11'	0.2854 (6)	0.6374 (6)	−0.0151 (2)	0.0152 (7)	0.157 (2)
N12'	0.3109 (6)	0.5477 (5)	−0.0553 (2)	0.0181 (7)	0.157 (2)
C13'	0.3517 (17)	0.6004 (14)	−0.1008 (4)	0.0196 (13)	0.157 (2)
H13'	0.3669	0.5418	−0.1319	0.024*	0.157 (2)
C14'	0.370 (3)	0.751 (3)	−0.0985 (10)	0.031 (4)	0.157 (2)
H14'	0.4076	0.7883	−0.1313	0.037*	0.157 (2)
C15'	0.354 (4)	0.843 (3)	−0.0690 (12)	0.033 (4)	0.157 (2)
H15'	0.3712	0.9445	−0.0774	0.040*	0.157 (2)
C16'	0.3060 (19)	0.7972 (15)	−0.0203 (5)	0.031 (2)	0.157 (2)
H16'	0.2877	0.8645	0.0081	0.038*	0.157 (2)
C21'	0.2083 (6)	0.4328 (5)	0.0457 (2)	0.0150 (7)	0.157 (2)
N22'	0.2169 (6)	0.3254 (6)	0.0084 (2)	0.0165 (7)	0.157 (2)
C23'	0.1879 (10)	0.1822 (8)	0.0185 (3)	0.0170 (9)	0.157 (2)
H23'	0.1918	0.1088	−0.0091	0.020*	0.157 (2)
C24'	0.154 (2)	0.1461 (18)	0.0679 (5)	0.025 (2)	0.157 (2)
H24'	0.1414	0.0439	0.0762	0.030*	0.157 (2)
C25'	0.1350 (18)	0.2471 (16)	0.1074 (4)	0.027 (2)	0.157 (2)
H25'	0.1004	0.2170	0.1415	0.033*	0.157 (2)
C26'	0.1670 (9)	0.3941 (7)	0.0972 (3)	0.0197 (9)	0.157 (2)
H26'	0.1611	0.4674	0.1246	0.024*	0.157 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0128 (2)	0.0128 (2)	0.01187 (19)	−0.00021 (16)	0.00241 (15)	−0.00070 (16)
C2	0.01252 (19)	0.01161 (19)	0.01139 (18)	−0.00002 (15)	0.00312 (15)	−0.00127 (15)
C3	0.0149 (2)	0.0165 (2)	0.0159 (2)	0.00070 (18)	0.00460 (18)	−0.00426 (18)
C4	0.0218 (3)	0.0203 (3)	0.0180 (2)	0.0012 (2)	0.0063 (2)	−0.0074 (2)
C5	0.0234 (3)	0.0213 (3)	0.0161 (2)	−0.0009 (2)	0.0026 (2)	−0.0077 (2)
C6	0.0167 (2)	0.0196 (3)	0.0154 (2)	−0.0010 (2)	0.00018 (19)	−0.0047 (2)
C7	0.0119 (2)	0.0135 (2)	0.0143 (2)	0.00021 (16)	0.00195 (16)	−0.00025 (16)
O1	0.0215 (2)	0.01339 (19)	0.0308 (3)	0.00298 (17)	0.0088 (2)	0.00323 (18)
O2	0.01606 (19)	0.0170 (2)	0.0244 (2)	0.00133 (16)	0.00974 (17)	0.00284 (17)
C8	0.01211 (19)	0.01270 (19)	0.01209 (19)	−0.00031 (16)	0.00334 (15)	−0.00148 (16)
O3	0.0149 (2)	0.0369 (3)	0.0180 (2)	−0.0017 (2)	0.00614 (16)	−0.0128 (2)
O4	0.01225 (17)	0.0200 (2)	0.0184 (2)	−0.00273 (15)	0.00383 (14)	−0.00658 (16)
N1	0.0190 (3)	0.0124 (2)	0.0124 (2)	−0.00179 (19)	0.00221 (19)	−0.00095 (17)
C11	0.0138 (3)	0.0138 (3)	0.0138 (3)	−0.0008 (2)	0.0023 (2)	0.0003 (2)
N12	0.0214 (3)	0.0121 (3)	0.0183 (3)	−0.0013 (2)	0.0072 (2)	−0.0010 (2)
C13	0.0276 (6)	0.0137 (4)	0.0257 (7)	−0.0022 (3)	0.0100 (6)	0.0017 (4)
C14	0.0245 (6)	0.0157 (8)	0.0294 (9)	−0.0020 (5)	0.0091 (6)	0.0057 (6)
C15	0.0231 (8)	0.0217 (7)	0.0259 (11)	−0.0025 (5)	0.0017 (6)	0.0086 (6)
C16	0.0228 (6)	0.0220 (6)	0.0150 (6)	−0.0017 (4)	0.0034 (4)	0.0009 (5)
C21	0.0142 (3)	0.0113 (3)	0.0134 (3)	−0.0003 (2)	0.0012 (2)	−0.0005 (2)
N22	0.0193 (3)	0.0128 (2)	0.0142 (3)	−0.0010 (2)	0.0052 (2)	−0.0014 (2)
C23	0.0261 (4)	0.0171 (4)	0.0161 (4)	−0.0021 (3)	0.0080 (4)	−0.0011 (3)
C24	0.0257 (5)	0.0178 (4)	0.0184 (5)	−0.0021 (3)	0.0061 (6)	0.0042 (5)
C25	0.0238 (6)	0.0152 (4)	0.0199 (8)	−0.0017 (4)	0.0046 (5)	0.0044 (5)
C26	0.0218 (4)	0.0115 (4)	0.0165 (4)	−0.0008 (3)	0.0014 (3)	−0.0010 (3)
N1'	0.0237 (18)	0.0136 (13)	0.0206 (16)	0.0010 (12)	0.0067 (13)	−0.0008 (11)
C11'	0.0163 (16)	0.0126 (15)	0.0170 (17)	−0.0003 (12)	0.0039 (13)	−0.0007 (14)
N12'	0.0189 (16)	0.0208 (17)	0.0147 (15)	0.0007 (13)	0.0024 (13)	−0.0028 (13)
C13'	0.022 (3)	0.019 (2)	0.017 (3)	0.004 (2)	0.000 (2)	−0.002 (3)
C14'	0.025 (6)	0.053 (9)	0.017 (3)	0.002 (5)	0.011 (3)	0.013 (4)
C15'	0.035 (5)	0.023 (7)	0.042 (11)	−0.002 (5)	0.008 (6)	0.013 (5)
C16'	0.025 (3)	0.043 (5)	0.026 (4)	0.009 (3)	0.003 (3)	−0.013 (3)
C21'	0.0156 (15)	0.0127 (14)	0.0172 (18)	0.0014 (11)	0.0043 (13)	0.0006 (14)
N22'	0.0164 (14)	0.0156 (16)	0.0171 (15)	−0.0009 (12)	0.0015 (12)	−0.0009 (13)
C23'	0.023 (2)	0.013 (2)	0.016 (2)	−0.0024 (19)	0.0055 (16)	−0.0012 (16)
C24'	0.018 (2)	0.043 (6)	0.016 (3)	0.005 (3)	0.004 (2)	0.000 (3)
C25'	0.022 (2)	0.036 (5)	0.023 (4)	−0.003 (3)	0.001 (3)	0.017 (4)
C26'	0.022 (2)	0.020 (2)	0.017 (2)	0.0009 (15)	0.0041 (19)	−0.0053 (18)

Geometric parameters (Å, º)

C1—C6	1.3979 (9)	N22—C23	1.3552 (13)
C1—C2	1.4007 (10)	C23—C24	1.375 (2)
C1—C7	1.5031 (9)	C23—H23	0.9500
C2—C3	1.3957 (9)	C24—C25	1.400 (3)
C2—C8	1.5099 (9)	C24—H24	0.9500
C3—C4	1.3931 (10)	C25—C26	1.378 (2)
C3—H3	0.955 (14)	C25—H25	0.9500
C4—C5	1.3909 (13)	C26—H26	0.9500
C4—H4	0.969 (15)	N1'—C21'	1.369 (6)
C5—C6	1.3924 (11)	N1'—C11'	1.411 (6)
C5—H5	0.981 (15)	N1'—H1'	0.8800
C6—H6	0.955 (14)	C11'—N12'	1.311 (8)
C7—O1	1.2141 (9)	C11'—C16'	1.454 (14)
C7—O2	1.3258 (9)	N12'—C13'	1.292 (11)
O2—H0	0.869 (14)	C13'—C14'	1.36 (3)
C8—O3	1.2412 (8)	C13'—H13'	0.9500
C8—O4	1.2772 (9)	C14'—C15'	1.12 (3)
N1—C21	1.3564 (11)	C14'—H14'	0.9500
N1—C11	1.3917 (11)	C15'—C16'	1.36 (3)
N1—H1	0.875 (16)	C15'—H15'	0.9500
C11—N12	1.3310 (14)	C16'—H16'	0.9500
C11—C16	1.4033 (18)	C21'—N22'	1.341 (7)
N12—C13	1.3342 (17)	C21'—C26'	1.389 (8)
C13—C14	1.391 (5)	N22'—C23'	1.335 (8)
C13—H13	0.9500	C23'—C24'	1.319 (14)
C14—C15	1.423 (5)	C23'—H23'	0.9500
C14—H14	0.9500	C24'—C25'	1.352 (18)
C15—C16	1.392 (4)	C24'—H24'	0.9500
C15—H15	0.9500	C25'—C26'	1.373 (15)
C16—H16	0.9500	C25'—H25'	0.9500
C21—N22	1.3484 (13)	C26'—H26'	0.9500
C21—C26	1.4129 (14)
C6—C1—C2	120.08 (6)	N22—C23—C24	120.63 (11)
C6—C1—C7	116.53 (6)	N22—C23—H23	119.7
C2—C1—C7	123.29 (6)	C24—C23—H23	119.7
C3—C2—C1	118.91 (6)	C23—C24—C25	118.81 (14)
C3—C2—C8	121.20 (6)	C23—C24—H24	120.6
C1—C2—C8	119.82 (5)	C25—C24—H24	120.6
C4—C3—C2	120.99 (7)	C26—C25—C24	119.85 (16)
C4—C3—H3	118.0 (8)	C26—C25—H25	120.1
C2—C3—H3	120.9 (8)	C24—C25—H25	120.1
C5—C4—C3	119.83 (7)	C25—C26—C21	119.83 (13)
C5—C4—H4	120.9 (9)	C25—C26—H26	120.1
C3—C4—H4	119.2 (9)	C21—C26—H26	120.1
C4—C5—C6	119.82 (7)	C21'—N1'—C11'	126.9 (5)
C4—C5—H5	122.0 (9)	C21'—N1'—H1'	116.5
C6—C5—H5	118.2 (9)	C11'—N1'—H1'	116.5
C5—C6—C1	120.35 (7)	N12'—C11'—N1'	119.9 (4)
C5—C6—H6	119.2 (8)	N12'—C11'—C16'	120.9 (6)
C1—C6—H6	120.4 (8)	N1'—C11'—C16'	119.2 (6)
O1—C7—O2	124.01 (6)	C13'—N12'—C11'	120.4 (7)
O1—C7—C1	123.10 (6)	N12'—C13'—C14'	111.3 (11)
O2—C7—C1	112.47 (6)	N12'—C13'—H13'	124.4
C7—O2—H0	111.6 (10)	C14'—C13'—H13'	124.4
O3—C8—O4	123.94 (6)	C15'—C14'—C13'	138 (2)
O3—C8—C2	117.21 (6)	C15'—C14'—H14'	110.9
O4—C8—C2	118.85 (6)	C13'—C14'—H14'	110.9
C21—N1—C11	127.17 (8)	C14'—C15'—C16'	114 (2)
C21—N1—H1	114.8 (11)	C14'—C15'—H15'	122.8
C11—N1—H1	117.8 (11)	C16'—C15'—H15'	122.8
N12—C11—N1	118.13 (8)	C15'—C16'—C11'	114.9 (11)
N12—C11—C16	122.95 (12)	C15'—C16'—H16'	122.5
N1—C11—C16	118.92 (13)	C11'—C16'—H16'	122.5
C11—N12—C13	118.29 (10)	N22'—C21'—N1'	121.8 (5)
N12—C13—C14	123.2 (2)	N22'—C21'—C26'	118.8 (4)
N12—C13—H13	118.4	N1'—C21'—C26'	119.4 (5)
C14—C13—H13	118.4	C23'—N22'—C21'	123.0 (5)
C13—C14—C15	119.1 (3)	C24'—C23'—N22'	117.7 (8)
C13—C14—H14	120.4	C24'—C23'—H23'	121.2
C15—C14—H14	120.4	N22'—C23'—H23'	121.2
C16—C15—C14	116.8 (4)	C23'—C24'—C25'	123.4 (13)
C16—C15—H15	121.6	C23'—C24'—H24'	118.3
C14—C15—H15	121.6	C25'—C24'—H24'	118.3
C15—C16—C11	119.6 (2)	C24'—C25'—C26'	118.6 (10)
C15—C16—H16	120.2	C24'—C25'—H25'	120.7
C11—C16—H16	120.2	C26'—C25'—H25'	120.7
N22—C21—N1	121.56 (8)	C25'—C26'—C21'	118.3 (6)
N22—C21—C26	118.44 (8)	C25'—C26'—H26'	120.8
N1—C21—C26	120.00 (9)	C21'—C26'—H26'	120.8
C21—N22—C23	122.38 (8)
C6—C1—C2—C3	−1.20 (10)	C11—N1—C21—C26	−178.45 (9)
C7—C1—C2—C3	175.11 (6)	N1—C21—N22—C23	−177.45 (9)
C6—C1—C2—C8	175.81 (6)	C26—C21—N22—C23	2.17 (14)
C7—C1—C2—C8	−7.88 (9)	C21—N22—C23—C24	−0.29 (19)
C1—C2—C3—C4	0.84 (10)	N22—C23—C24—C25	−1.7 (3)
C8—C2—C3—C4	−176.12 (7)	C23—C24—C25—C26	1.8 (4)
C2—C3—C4—C5	0.15 (12)	C24—C25—C26—C21	0.1 (3)
C3—C4—C5—C6	−0.80 (13)	N22—C21—C26—C25	−2.0 (2)
C4—C5—C6—C1	0.44 (12)	N1—C21—C26—C25	177.59 (16)
C2—C1—C6—C5	0.57 (11)	C21'—N1'—C11'—N12'	−2.2 (8)
C7—C1—C6—C5	−175.99 (7)	C21'—N1'—C11'—C16'	178.1 (7)
C6—C1—C7—O1	99.79 (8)	N1'—C11'—N12'—C13'	179.0 (7)
C2—C1—C7—O1	−76.64 (9)	C16'—C11'—N12'—C13'	−1.3 (11)
C6—C1—C7—O2	−73.09 (8)	C11'—N12'—C13'—C14'	2.6 (17)
C2—C1—C7—O2	110.47 (7)	N12'—C13'—C14'—C15'	−4 (5)
C3—C2—C8—O3	163.04 (7)	C13'—C14'—C15'—C16'	2 (6)
C1—C2—C8—O3	−13.90 (9)	C14'—C15'—C16'—C11'	0 (4)
C3—C2—C8—O4	−16.07 (9)	N12'—C11'—C16'—C15'	0 (2)
C1—C2—C8—O4	166.99 (6)	N1'—C11'—C16'—C15'	179.4 (17)
C21—N1—C11—N12	0.20 (13)	C11'—N1'—C21'—N22'	−1.9 (8)
C21—N1—C11—C16	−179.95 (13)	C11'—N1'—C21'—C26'	178.4 (5)
N1—C11—N12—C13	−178.58 (13)	N1'—C21'—N22'—C23'	−179.8 (5)
C16—C11—N12—C13	1.6 (2)	C26'—C21'—N22'—C23'	−0.1 (8)
C11—N12—C13—C14	0.2 (4)	C21'—N22'—C23'—C24'	−1.6 (12)
N12—C13—C14—C15	−1.4 (6)	N22'—C23'—C24'—C25'	4 (2)
C13—C14—C15—C16	0.9 (6)	C23'—C24'—C25'—C26'	−5 (2)
C14—C15—C16—C11	0.7 (5)	C24'—C25'—C26'—C21'	3.1 (15)
N12—C11—C16—C15	−2.0 (3)	N22'—C21'—C26'—C25'	−0.7 (10)
N1—C11—C16—C15	178.1 (3)	N1'—C21'—C26'—C25'	179.1 (7)
C11—N1—C21—N22	1.17 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H0···O4^i	0.869 (14)	1.753 (14)	2.6103 (11)	168.6 (15)
N1—H1···O4^ii	0.875 (16)	1.882 (16)	2.7565 (9)	177.3 (16)
N1—H1···O3^ii	0.875 (16)	2.579 (16)	3.1236 (12)	121.2 (12)
N1′—H1′···O3^iii	0.88	1.82	2.604 (4)	147

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