Hydrogen bonding in two benzene-1,2-diaminium pyridine-2-carboxyl­ate salts and a cocrystal of benzene-1,2-di­amine and benzoic acid

The isostructural salts benzene-1,2-diaminium bis­(pyridine-2-carboxyl­ate), 0.5C₆H₁₀N₂²⁺·C₆H₄NO₂⁻, (1), and 4,5-di­methyl­benzene-1,2-diaminium bis(pyri­dine-2-carboxyl­ate), 0.5C₈H₁₄N₂²⁺·C₆H₄NO₂⁻, (2), and the 1:2 benzene-1,2-di­amine–benzoic acid cocrystal, 0.5C₆H₈N₂·C₇H₆O₂, (3), are reported. All of the compounds exhibit extensive N—H...O hydrogen bonding that results in inter­connected rings. O—H...N hydrogen bonding is observed in (3). Additional π–π and C—H...π inter­actions are found in each compound. Hirshfeld and fingerprint plot analyses reveal the primary inter­molecular inter­actions and density functional theory was used to calculate their strengths. Salt formation by (1) and (2), and cocrystallization by (3) are rationalized by examining pK_a differences. The R₂²(9) hydrogen-bonding motif is common to each of these structures.

Computing details

For all structures, data collection: APEX2 (Bruker, 2015); cell refinement: APEX2 (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Benzene-1,2-diaminium bis(pyridine-2-carboxylate) (1)

Crystal data

0.5C6H10N2^2+·C6H4NO2^−	F(000) = 744
Mr = 177.18	Dx = 1.365 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.467 (5) Å	Cell parameters from 2197 reflections
b = 7.675 (2) Å	θ = 2.3–23.1°
c = 12.837 (3) Å	µ = 0.10 mm^−1
β = 125.362 (7)°	T = 200 K
V = 1724.8 (7) Å^3	Prism, clear brown
Z = 8	0.50 × 0.30 × 0.25 mm

Data collection

Bruker SMART X2S benchtop diffractometer	1573 independent reflections
Radiation source: XOS X-beam microfocus source	1161 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.063
Detector resolution: 8.3330 pixels mm^-1	θmax = 25.4°, θmin = 2.3°
ω scans	h = −25→25
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −9→6
Tmin = 0.61, Tmax = 0.98	l = −15→14
8287 measured reflections

Refinement

Refinement on F^2	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.138	w = 1/[σ^2(Fo^2) + (0.0685P)^2 + 0.2917P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1573 reflections	Δρmax = 0.20 e Å^−3
130 parameters	Δρmin = −0.26 e Å^−3

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
N1	0.45266 (9)	0.5387 (2)	0.61312 (15)	0.0373 (4)
H1A	0.4185 (11)	0.559 (3)	0.5265 (15)	0.058 (6)*
H1B	0.4267 (11)	0.464 (2)	0.6356 (19)	0.058 (6)*
H1C	0.4938 (12)	0.470 (3)	0.624 (2)	0.082 (7)*
C1	0.47781 (9)	0.7015 (2)	0.68382 (16)	0.0348 (4)
C2	0.45715 (11)	0.8578 (2)	0.6183 (2)	0.0494 (5)
H2	0.4278	0.8585	0.5277	0.059*
C3	0.47923 (14)	1.0128 (3)	0.6850 (2)	0.0671 (6)
H3	0.4654	1.1202	0.6401	0.081*
O1	0.57010 (7)	0.38679 (19)	0.63284 (13)	0.0546 (4)
O2	0.64209 (8)	0.36981 (19)	0.84518 (13)	0.0583 (5)
C4	0.63292 (11)	0.3725 (2)	0.73992 (18)	0.0416 (5)
N2	0.69229 (9)	0.3856 (2)	0.62789 (14)	0.0456 (4)
C5	0.70385 (10)	0.3601 (2)	0.74123 (16)	0.0370 (4)
C6	0.77514 (11)	0.3280 (3)	0.85123 (18)	0.0501 (5)
H6	0.7817	0.31	0.9303	0.06*
C7	0.83688 (11)	0.3225 (3)	0.8442 (2)	0.0614 (6)
H7	0.8866	0.2985	0.9183	0.074*
C8	0.82608 (12)	0.3519 (3)	0.7301 (2)	0.0601 (6)
H8	0.8681	0.3509	0.7239	0.072*
C9	0.75375 (12)	0.3828 (3)	0.6250 (2)	0.0560 (6)
H9	0.7466	0.4034	0.5458	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0343 (8)	0.0485 (9)	0.0300 (9)	0.0001 (6)	0.0191 (7)	−0.0001 (7)
C1	0.0282 (8)	0.0462 (10)	0.0342 (9)	−0.0011 (7)	0.0204 (7)	−0.0006 (7)
C2	0.0485 (11)	0.0541 (12)	0.0388 (12)	0.0013 (9)	0.0212 (10)	0.0054 (9)
C3	0.0789 (15)	0.0464 (12)	0.0541 (13)	0.0022 (11)	0.0259 (12)	0.0083 (10)
O1	0.0353 (7)	0.0875 (11)	0.0418 (9)	0.0081 (6)	0.0228 (7)	−0.0003 (7)
O2	0.0554 (9)	0.0876 (11)	0.0445 (9)	0.0184 (7)	0.0362 (8)	0.0113 (7)
C4	0.0426 (11)	0.0479 (10)	0.0395 (12)	0.0071 (8)	0.0268 (10)	0.0030 (8)
N2	0.0367 (8)	0.0653 (11)	0.0371 (10)	0.0045 (7)	0.0227 (8)	0.0015 (7)
C5	0.0363 (10)	0.0433 (10)	0.0326 (11)	0.0045 (7)	0.0206 (9)	−0.0001 (7)
C6	0.0428 (11)	0.0667 (13)	0.0366 (11)	0.0098 (9)	0.0204 (9)	0.0009 (9)
C7	0.0350 (11)	0.0840 (16)	0.0522 (14)	0.0127 (10)	0.0178 (10)	−0.0041 (11)
C8	0.0404 (11)	0.0846 (16)	0.0636 (15)	0.0054 (10)	0.0349 (11)	−0.0058 (11)
C9	0.0497 (12)	0.0811 (15)	0.0500 (13)	0.0058 (10)	0.0361 (11)	0.0015 (11)

Geometric parameters (Å, º)

N1—C1	1.453 (2)	C4—C5	1.516 (2)
N1—H1A	0.925 (16)	N2—C9	1.341 (2)
N1—H1B	0.955 (15)	N2—C5	1.341 (2)
N1—H1C	0.969 (16)	C5—C6	1.377 (3)
C1—C2	1.382 (2)	C6—C7	1.381 (3)
C1—C1^i	1.386 (3)	C6—H6	0.95
C2—C3	1.380 (3)	C7—C8	1.362 (3)
C2—H2	0.95	C7—H7	0.95
C3—C3^i	1.362 (5)	C8—C9	1.365 (3)
C3—H3	0.95	C8—H8	0.95
O1—C4	1.255 (2)	C9—H9	0.95
O2—C4	1.248 (2)
C1—N1—H1A	111.0 (14)	O1—C4—C5	116.96 (15)
C1—N1—H1B	113.7 (12)	C9—N2—C5	117.39 (17)
H1A—N1—H1B	105.6 (18)	N2—C5—C6	122.46 (16)
C1—N1—H1C	113.7 (15)	N2—C5—C4	115.13 (16)
H1A—N1—H1C	106.5 (18)	C6—C5—C4	122.40 (16)
H1B—N1—H1C	105.9 (19)	C5—C6—C7	118.53 (18)
C2—C1—C1^i	119.77 (11)	C5—C6—H6	120.7
C2—C1—N1	119.62 (16)	C7—C6—H6	120.7
C1^i—C1—N1	120.61 (9)	C8—C7—C6	119.54 (19)
C3—C2—C1	119.8 (2)	C8—C7—H7	120.2
C3—C2—H2	120.1	C6—C7—H7	120.2
C1—C2—H2	120.1	C7—C8—C9	118.68 (18)
C3^i—C3—C2	120.42 (12)	C7—C8—H8	120.7
C3^i—C3—H3	119.8	C9—C8—H8	120.7
C2—C3—H3	119.8	N2—C9—C8	123.38 (19)
O2—C4—O1	125.73 (16)	N2—C9—H9	118.3
O2—C4—C5	117.31 (17)	C8—C9—H9	118.3
C1^i—C1—C2—C3	−1.6 (3)	O1—C4—C5—C6	−173.88 (18)
N1—C1—C2—C3	178.30 (17)	N2—C5—C6—C7	0.2 (3)
C1—C2—C3—C3^i	−0.5 (4)	C4—C5—C6—C7	−178.61 (18)
C9—N2—C5—C6	−1.5 (3)	C5—C6—C7—C8	1.2 (3)
C9—N2—C5—C4	177.41 (16)	C6—C7—C8—C9	−1.2 (3)
O2—C4—C5—N2	−171.91 (16)	C5—N2—C9—C8	1.5 (3)
O1—C4—C5—N2	7.2 (2)	C7—C8—C9—N2	−0.1 (4)
O2—C4—C5—C6	7.0 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

Cg(bdaH₂²⁺) refers to the ring centroid of the benzene-1,2-diaminium cation.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^ii	0.93 (2)	2.24 (2)	2.958 (2)	135 (2)
N1—H1A···N2^ii	0.93 (2)	2.08 (2)	2.907 (2)	149 (2)
N1—H1B···O2^i	0.96 (2)	1.78 (2)	2.7137 (19)	164 (2)
N1—H1C···O1	0.97 (2)	1.70 (2)	2.6533 (19)	168 (2)
C8—H8···Cg(bdaH2^2+)^iii	0.95	2.65	3.592 (3)	170

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

4,5-Dimethylbenzene-1,2-diaminium bis(pyridine-2-carboxylate) (2)

Crystal data

0.5C8H14N2^2+·C6H4NO2^−	F(000) = 808
Mr = 191.21	Dx = 1.252 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.451 (4) Å	Cell parameters from 2093 reflections
b = 9.0100 (19) Å	θ = 2.5–23.6°
c = 12.585 (3) Å	µ = 0.09 mm^−1
β = 123.447 (6)°	T = 200 K
V = 2029.5 (7) Å^3	Block, clear colourless
Z = 8	0.60 × 0.50 × 0.25 mm

Data collection

Bruker SMART X2S benchtop diffractometer	1794 independent reflections
Radiation source: XOS X-beam microfocus source	1201 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.080
Detector resolution: 8.3330 pixels mm^-1	θmax = 25.4°, θmin = 2.5°
ω scans	h = −25→25
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −10→10
Tmin = 0.61, Tmax = 0.98	l = −15→14
7764 measured reflections

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: mixed
wR(F^2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0512P)^2] where P = (Fo^2 + 2Fc^2)/3
1794 reflections	(Δ/σ)max < 0.001
140 parameters	Δρmax = 0.14 e Å^−3
3 restraints	Δρmin = −0.19 e Å^−3

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.

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 > 2sigma(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
O1	0.42726 (7)	0.91055 (15)	0.36543 (11)	0.0570 (4)
O2	0.35918 (7)	0.87343 (16)	0.15592 (11)	0.0620 (4)
N1	0.30655 (9)	0.89341 (16)	0.37525 (13)	0.0501 (4)
N2	0.54686 (9)	0.02590 (15)	0.38711 (13)	0.0381 (4)
H2A	0.5757 (10)	−0.034 (2)	0.3665 (19)	0.071 (6)*
H2B	0.5048 (9)	−0.028 (2)	0.3788 (17)	0.066 (6)*
H2C	0.5774 (9)	0.046 (2)	0.4716 (14)	0.058 (6)*
C1	0.36696 (10)	0.87944 (17)	0.26126 (16)	0.0428 (5)
C2	0.30035 (9)	0.84935 (18)	0.26854 (14)	0.0397 (4)
C3	0.23710 (10)	0.7799 (2)	0.16953 (16)	0.0523 (5)
H3	0.2342	0.7504	0.0945	0.063*
C4	0.17839 (10)	0.7550 (2)	0.18321 (19)	0.0625 (6)
H4	0.1348	0.7046	0.1186	0.075*
C5	0.18355 (11)	0.8033 (2)	0.29038 (19)	0.0662 (6)
H5	0.1431	0.7897	0.3003	0.079*
C6	0.24789 (12)	0.8718 (2)	0.38375 (19)	0.0620 (6)
H6	0.2509	0.9054	0.458	0.074*
C7	0.52181 (8)	0.16447 (17)	0.31600 (14)	0.0351 (4)
C8	0.54091 (9)	0.29813 (18)	0.38044 (15)	0.0438 (5)
H8	0.5689	0.2977	0.4709	0.053*
C9	0.52030 (10)	0.4332 (2)	0.31640 (17)	0.0520 (5)
C10	0.54175 (15)	0.5765 (2)	0.3908 (2)	0.0838 (8)
H10A	0.5755	0.6329	0.3764	0.126*
H10B	0.567	0.5543	0.4817	0.126*
H10C	0.4967	0.6351	0.3624	0.126*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0424 (8)	0.0826 (10)	0.0510 (8)	−0.0109 (6)	0.0289 (7)	0.0005 (6)
O2	0.0674 (9)	0.0805 (10)	0.0570 (8)	−0.0222 (7)	0.0462 (7)	−0.0156 (6)
N1	0.0465 (10)	0.0648 (10)	0.0475 (9)	−0.0058 (7)	0.0312 (7)	−0.0022 (7)
N2	0.0395 (9)	0.0422 (8)	0.0363 (8)	0.0010 (6)	0.0233 (7)	0.0011 (5)
C1	0.0464 (12)	0.0418 (9)	0.0466 (10)	−0.0046 (8)	0.0296 (9)	−0.0018 (7)
C2	0.0401 (11)	0.0426 (9)	0.0405 (9)	−0.0013 (7)	0.0247 (8)	0.0027 (6)
C3	0.0509 (12)	0.0557 (11)	0.0504 (11)	−0.0101 (9)	0.0279 (9)	−0.0037 (8)
C4	0.0429 (13)	0.0680 (13)	0.0675 (14)	−0.0153 (9)	0.0246 (10)	0.0040 (10)
C5	0.0474 (14)	0.0874 (17)	0.0781 (15)	−0.0065 (11)	0.0435 (12)	0.0096 (11)
C6	0.0559 (13)	0.0867 (15)	0.0595 (12)	−0.0032 (11)	0.0419 (11)	−0.0009 (10)
C7	0.0320 (10)	0.0399 (9)	0.0411 (8)	0.0003 (6)	0.0250 (7)	−0.0001 (6)
C8	0.0445 (11)	0.0479 (10)	0.0443 (10)	−0.0048 (8)	0.0278 (8)	−0.0043 (6)
C9	0.0557 (12)	0.0432 (10)	0.0662 (11)	−0.0033 (8)	0.0394 (10)	−0.0066 (7)
C10	0.117 (2)	0.0473 (12)	0.0915 (16)	−0.0099 (12)	0.0600 (15)	−0.0141 (9)

Geometric parameters (Å, º)

O1—C1	1.265 (2)	C4—H4	0.95
O2—C1	1.243 (2)	C5—C6	1.371 (3)
N1—C6	1.334 (2)	C5—H5	0.95
N1—C2	1.335 (2)	C6—H6	0.95
N2—C7	1.455 (2)	C7—C8	1.382 (2)
N2—H2A	0.959 (16)	C7—C7^i	1.386 (3)
N2—H2B	0.979 (15)	C8—C9	1.390 (2)
N2—H2C	0.908 (14)	C8—H8	0.95
C1—C2	1.506 (3)	C9—C9^i	1.395 (4)
C2—C3	1.386 (2)	C9—C10	1.510 (2)
C3—C4	1.380 (3)	C10—H10A	0.98
C3—H3	0.95	C10—H10B	0.98
C4—C5	1.363 (3)	C10—H10C	0.98
C6—N1—C2	117.50 (16)	C4—C5—H5	120.4
C7—N2—H2A	113.1 (13)	C6—C5—H5	120.4
C7—N2—H2B	110.8 (11)	N1—C6—C5	123.06 (19)
H2A—N2—H2B	112.6 (17)	N1—C6—H6	118.5
C7—N2—H2C	109.7 (11)	C5—C6—H6	118.5
H2A—N2—H2C	105.7 (16)	C8—C7—C7^i	119.29 (9)
H2B—N2—H2C	104.5 (17)	C8—C7—N2	119.81 (14)
O2—C1—O1	125.06 (17)	C7^i—C7—N2	120.89 (8)
O2—C1—C2	118.88 (15)	C7—C8—C9	121.73 (16)
O1—C1—C2	116.05 (15)	C7—C8—H8	119.1
N1—C2—C3	122.95 (17)	C9—C8—H8	119.1
N1—C2—C1	115.85 (14)	C8—C9—C9^i	118.90 (10)
C3—C2—C1	121.20 (16)	C8—C9—C10	119.88 (18)
C4—C3—C2	118.02 (18)	C9^i—C9—C10	121.22 (12)
C4—C3—H3	121.0	C9—C10—H10A	109.5
C2—C3—H3	121.0	C9—C10—H10B	109.5
C5—C4—C3	119.31 (18)	H10A—C10—H10B	109.5
C5—C4—H4	120.3	C9—C10—H10C	109.5
C3—C4—H4	120.3	H10A—C10—H10C	109.5
C4—C5—C6	119.1 (2)	H10B—C10—H10C	109.5
C6—N1—C2—C3	−1.6 (3)	C2—C3—C4—C5	2.2 (3)
C6—N1—C2—C1	178.42 (15)	C3—C4—C5—C6	−1.9 (3)
O2—C1—C2—N1	−163.60 (16)	C2—N1—C6—C5	2.0 (3)
O1—C1—C2—N1	15.8 (2)	C4—C5—C6—N1	−0.2 (3)
O2—C1—C2—C3	16.5 (3)	C7^i—C7—C8—C9	−2.9 (3)
O1—C1—C2—C3	−164.09 (16)	N2—C7—C8—C9	177.82 (16)
N1—C2—C3—C4	−0.4 (3)	C7—C8—C9—C9^i	−0.4 (3)
C1—C2—C3—C4	179.53 (16)	C7—C8—C9—C10	179.38 (18)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

Cg(Me₂bdaH₂²⁺) refers to the ring centroid of the 4,5-dimethyl-benzene-1,2-diaminium cation.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2^ii	0.96 (2)	1.78 (2)	2.729 (2)	171 (2)
N2—H2B···O1^iii	0.98 (2)	1.67 (2)	2.639 (2)	169 (2)
N2—H2C···O1^iv	0.91 (1)	2.14 (2)	2.9032 (19)	141 (2)
N2—H2C···N1^iv	0.91 (1)	2.22 (2)	2.999 (2)	144 (2)
C5—H5···Cg(Me2bdaH2^2+)^v	0.95	2.77	3.682 (3)	160

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

Benzene-1,2-diamine bis(benzoic acid) (3)

Crystal data

0.5C6H8N2·C7H6O2	Dx = 1.272 Mg m^−3
Mr = 176.19	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 4994 reflections
a = 20.061 (3) Å	θ = 2.8–24.2°
b = 7.8464 (10) Å	µ = 0.09 mm^−1
c = 11.6895 (12) Å	T = 200 K
V = 1840.0 (4) Å^3	Plate, clear colourless
Z = 8	0.60 × 0.48 × 0.20 mm
F(000) = 744

Data collection

Bruker SMART X2S benchtop diffractometer	1638 independent reflections
Radiation source: XOS X-beam microfocus source	1337 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.064
Detector resolution: 8.3330 pixels mm^-1	θmax = 25.2°, θmin = 2.8°
ω scans	h = −23→23
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −9→9
Tmin = 0.64, Tmax = 0.98	l = −13→13
30170 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)] = 0.030	w = 1/[σ^2(Fo^2) + (0.0426P)^2 + 0.2144P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.087	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.12 e Å^−3
1638 reflections	Δρmin = −0.12 e Å^−3
131 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015)
0 restraints	Extinction coefficient: 0.036 (2)

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	0.35377 (4)	0.51824 (13)	0.24544 (7)	0.0577 (3)
H1C	0.3984 (9)	0.489 (2)	0.2143 (15)	0.094 (5)*
O2	0.40648 (4)	0.59582 (12)	0.40443 (7)	0.0566 (3)
N1	0.46617 (5)	0.40589 (14)	0.14608 (9)	0.0445 (3)
H1A	0.4497 (7)	0.3912 (16)	0.0737 (13)	0.061 (4)*
H1B	0.5014 (8)	0.4803 (19)	0.1440 (12)	0.060 (4)*
C1	0.16309 (8)	0.6783 (2)	0.48889 (14)	0.0698 (4)
H1	0.1204	0.7037	0.5196	0.084*
C2	0.21951 (8)	0.71645 (18)	0.55063 (13)	0.0661 (4)
H2	0.2156	0.7662	0.6244	0.079*
C3	0.28164 (7)	0.68275 (16)	0.50592 (11)	0.0537 (4)
H3	0.3205	0.7097	0.5488	0.064*
C4	0.28756 (6)	0.60956 (14)	0.39861 (10)	0.0421 (3)
C5	0.35476 (6)	0.57469 (14)	0.35138 (10)	0.0425 (3)
C6	0.16825 (7)	0.6037 (2)	0.38286 (14)	0.0668 (4)
H6	0.1292	0.5757	0.341	0.08*
C7	0.23038 (6)	0.56947 (16)	0.33734 (12)	0.0534 (3)
H7	0.234	0.5184	0.2639	0.064*
C8	0.48442 (7)	−0.05934 (19)	0.19776 (14)	0.0703 (4)
H8	0.4736	−0.1642	0.1616	0.084*
C9	0.46876 (6)	0.09306 (17)	0.14506 (11)	0.0544 (4)
H9	0.4472	0.0922	0.0727	0.065*
C10	0.48419 (5)	0.24690 (15)	0.19649 (10)	0.0403 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0473 (5)	0.0887 (7)	0.0370 (5)	0.0157 (5)	−0.0043 (4)	−0.0083 (4)
O2	0.0435 (5)	0.0792 (6)	0.0470 (5)	0.0051 (4)	−0.0086 (4)	−0.0077 (4)
N1	0.0400 (6)	0.0623 (7)	0.0311 (6)	−0.0011 (5)	−0.0041 (4)	0.0016 (4)
C1	0.0568 (9)	0.0712 (9)	0.0815 (11)	0.0126 (7)	0.0262 (8)	0.0159 (8)
C2	0.0750 (10)	0.0680 (9)	0.0552 (9)	0.0142 (7)	0.0189 (7)	0.0008 (7)
C3	0.0589 (8)	0.0570 (7)	0.0452 (7)	0.0086 (6)	0.0016 (6)	−0.0003 (6)
C4	0.0444 (7)	0.0431 (6)	0.0387 (6)	0.0053 (5)	−0.0001 (5)	0.0060 (5)
C5	0.0456 (7)	0.0470 (6)	0.0350 (6)	0.0056 (5)	−0.0049 (5)	0.0033 (5)
C6	0.0423 (7)	0.0789 (10)	0.0793 (11)	−0.0010 (7)	0.0007 (7)	0.0119 (8)
C7	0.0472 (7)	0.0624 (8)	0.0505 (8)	0.0002 (6)	−0.0025 (6)	0.0028 (6)
C8	0.0651 (9)	0.0578 (8)	0.0879 (11)	−0.0009 (7)	−0.0181 (8)	−0.0114 (7)
C9	0.0448 (7)	0.0673 (8)	0.0512 (8)	0.0002 (6)	−0.0078 (6)	−0.0111 (6)
C10	0.0288 (5)	0.0570 (7)	0.0352 (6)	0.0012 (5)	0.0019 (4)	−0.0005 (5)

Geometric parameters (Å, º)

O1—C5	1.3153 (14)	C3—H3	0.95
O1—H1C	0.994 (19)	C4—C7	1.3885 (17)
O2—C5	1.2201 (14)	C4—C5	1.4822 (16)
N1—C10	1.4262 (15)	C6—C7	1.3816 (19)
N1—H1A	0.916 (15)	C6—H6	0.95
N1—H1B	0.916 (16)	C7—H7	0.95
C1—C6	1.375 (2)	C8—C8^i	1.372 (3)
C1—C2	1.375 (2)	C8—C9	1.3814 (19)
C1—H1	0.95	C8—H8	0.95
C2—C3	1.3771 (19)	C9—C10	1.3836 (17)
C2—H2	0.95	C9—H9	0.95
C3—C4	1.3848 (17)	C10—C10^i	1.403 (2)
C5—O1—H1C	114.1 (10)	O2—C5—C4	123.99 (11)
C10—N1—H1A	111.3 (8)	O1—C5—C4	113.52 (10)
C10—N1—H1B	111.9 (9)	C1—C6—C7	119.87 (14)
H1A—N1—H1B	109.5 (12)	C1—C6—H6	120.1
C6—C1—C2	120.25 (13)	C7—C6—H6	120.1
C6—C1—H1	119.9	C6—C7—C4	120.17 (13)
C2—C1—H1	119.9	C6—C7—H7	119.9
C1—C2—C3	120.26 (13)	C4—C7—H7	119.9
C1—C2—H2	119.9	C8^i—C8—C9	120.04 (8)
C3—C2—H2	119.9	C8^i—C8—H8	120.0
C2—C3—C4	120.07 (13)	C9—C8—H8	120.0
C2—C3—H3	120.0	C8—C9—C10	120.69 (12)
C4—C3—H3	120.0	C8—C9—H9	119.7
C3—C4—C7	119.36 (11)	C10—C9—H9	119.7
C3—C4—C5	119.48 (11)	C9—C10—C10^i	119.26 (7)
C7—C4—C5	121.16 (11)	C9—C10—N1	121.79 (11)
O2—C5—O1	122.49 (11)	C10^i—C10—N1	118.89 (6)
C6—C1—C2—C3	1.1 (2)	C2—C1—C6—C7	−1.1 (2)
C1—C2—C3—C4	−0.3 (2)	C1—C6—C7—C4	0.3 (2)
C2—C3—C4—C7	−0.53 (19)	C3—C4—C7—C6	0.52 (19)
C2—C3—C4—C5	179.74 (11)	C5—C4—C7—C6	−179.75 (11)
C3—C4—C5—O2	5.18 (18)	C8^i—C8—C9—C10	0.0 (3)
C7—C4—C5—O2	−174.54 (11)	C8—C9—C10—C10^i	−0.3 (2)
C3—C4—C5—O1	−174.73 (11)	C8—C9—C10—N1	−177.43 (12)
C7—C4—C5—O1	5.54 (16)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

Cg(bda) refers to the ring centroid of the benzene-1,2-diamine.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···N1	0.994 (19)	1.706 (19)	2.6852 (13)	167.8 (16)
N1—H1A···O2^ii	0.916 (15)	2.163 (16)	3.0681 (14)	169.8 (12)
N1—H1B···O2^i	0.916 (16)	2.136 (16)	3.0160 (14)	160.8 (12)
C6—H6···Cg(bda)^iii	0.95	2.81	3.7163 (16)	161

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