Crystal structure of a 1:1 cocrystal of nicotinamide with 2-chloro-5-nitro-benzoic acid.

In the title 1:1 cocrystal, C7H4ClNO4·C6H6N2O, nicotinamide (NIC) and 2-chloro-5-nitro-benzoic acid (CNBA) cocrystallize with one mol-ecule each of NIC and CNBA in the asymmetric unit. In this structure, CNBA and NIC form hydrogen bonds through O-H⋯N, N-H⋯O and C-H⋯O inter-actions along with N-H⋯O dimer hydrogen bonds of NIC. Further additional weak π-π inter-actions stabilize the mol-ecular assembly of this cocrystal. © Bairagi et al. 2019.

Chemical context

Nicotinamide (NIC) derivatives are used in various applications, for example, in the prevention of type 1 diabetes (Elliott et al., 1993 ▸) and nicotinamide cofactors are also used in preparative enzymatic synthesis (Chenault & Whitesides, 1987 ▸). The nicotinamide formulation has also been used for treatment in palliative radiotherapy (Horsman et al., 1993 ▸). The pharmacological result for the active pharmaceutical ingredient (API) will increase if it becomes cocrystallized with a coformer or other active com­ponent (Schultheiss & Newman, 2009 ▸; Lemmerer et al., 2010 ▸). Chloro­benzoic acid derivatives are widely used in the pharmaceutical industry. 2-Chloro-4-nitro­benzoic acid is used for immunodeficiency diseases as an anti­viral and anti­cancer agent (Lemmerer et al., 2010 ▸). In the title com­pound, NIC is cocrystallized with the CNBA coformer as it acts as an excellent candidate for cocrystallization because of the hydrogen-bond acceptor and donor parts (Dragovic et al., 1995 ▸).

Structural commentary

The title com­pound CNBA–NIC (1:1) crystallizes in the monoclinic space group P21/c with four mol­ecules of NIC and CNBA in the unit cell. The dihedral angle between the amide plane with the mean plane of the phenyl part in NIC is 23.87 (1)°, and the dihedral angles of the carboxyl and nitro groups with the chloro­phenyl ring in CNBA are 24.92 (1) and 3.56 (1)°, respectively. In the asymmetric unit, an (CNBA)O–H⋯N inter­action plays a prime role in the mol­ecular recognition of this cocrystal (Fig. 1 ▸).

Figure 1

The asymmetric unit of the title com­pound, showing 50% probability ellipsoids, the atom labelling and hydrogen bonding with dotted lines.

Supra­molecular features

In the crystal structure of the title cocrystal, a strong (CNBA)O—H⋯N(NIC) hydrogen bond and additional (NIC)N—H⋯O(CNBA) and (NIC)C—H⋯O(CNBA) hydrogen bonds are observed (Fig. 2 ▸ and Table 1 ▸). In this cocrystal, the NIC mol­ecule forms a dimer with itself having an (8) graph-set motif (Etter et al., 1990 ▸). These dimers are further connected via C—H⋯O hydrogen bonding and form a tetra­meric ring with two mol­ecules each of NIC and CNBA with (10) graph-set motifs (Etter et al., 1990 ▸) (Fig. 2 ▸). Furthermore, weak π–π inter­actions are observed for both NIC [3.68 (7) Å] and CNBA [3.73 (7) Å] which stabilize the mol­ecular assembly along the bc plane (Fig. 3 ▸).

Figure 2

Hydrogen bonds in the title com­pound showing the dimer formation through N—H⋯O inter­actions and tetra­mer formation through C—H⋯O inter­actions.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.90 (2)	2.005 (19)	2.9004 (15)	171.4 (14)
N1—H1B⋯O3	0.873 (19)	2.116 (19)	2.9715 (14)	166.6 (16)
O2—H2⋯N2	1.07 (2)	1.49 (2)	2.5543 (13)	172 (2)
C3—H3⋯O4	0.986 (15)	2.516 (15)	3.4505 (16)	158.2 (12)
C4—H4⋯O5	0.979 (14)	2.442 (15)	3.3256 (17)	149.9 (12)
C5—H5⋯O5	0.956 (15)	2.450 (16)	3.0878 (17)	124.0 (11)
C6—H6⋯O3	0.959 (15)	2.608 (15)	3.452 (1)	147.0 (11)
C10—H10⋯O4	0.955 (15)	2.599 (16)	3.5010 (18)	157.6 (15)

Figure 3

Weak π–π inter­actions stabilize the mol­ecular assembly of both mol­ecules in the crystal.

Hirshfeld surface analysis

To understand the role of inter­molecular inter­actions, we have utilized the Hirshfeld surface analysis visualizing tool (Spackman & Jayatilaka, 2009 ▸). The Hirshfeld surfaces and two-dimensional fingerprint plots developed using CrystalExplorer (Version 3.1; Wolff et al., 2012 ▸) are shown in Fig. 4 ▸. The red spot on the surface represents a strong inter­action through O—H⋯N and N—H⋯O hydrogen bonding, whereas the blue color represents a lack of inter­action. The d norm map of the title com­pound NIC·CNBA and its pure com­ponents is shown in Fig. 4 ▸, where individual mol­ecular inter­actions were estimated. The fingerprint plot shows that O⋯H/H⋯O and H⋯H contribute the major part of the inter­action in all com­pounds (Fig. 4 ▸). The O⋯H/H⋯O contact contributes 40% to the cocrystal NIC mol­ecule (Fig. 5 ▸) and 20.5% to the pure NIC mol­ecule (NICOAM01; Miwa et al., 1999 ▸) (Fig. 6 ▸), and H⋯H contributes 22% to the cocrystal NIC mol­ecule and 41% to the pure NIC mol­ecule. Similarly, O⋯H/H⋯O contacts contribute 33% to the cocrystal CNBA mol­ecule (Fig. 7 ▸) and 36.6% to the pure CNBA mol­ecule (CLNBZA; Ferguson & Sim, 1962 ▸) (Fig. 8 ▸), and H⋯H contributes 15.2% to the cocrystal CNBA mol­ecule and 17.7% to the pure NIC mol­ecule.

Figure 4

Hirshfeld surfaces developed on (i) d norm mapped over the pure NIC mol­ecule, (ii) d norm mapped over the NIC mol­ecule in title com­pound, (iii) d norm mapped over the pure CNBA mol­ecule and (iv) d norm mapped over the CNBA mol­ecule in title com­pound.

Figure 5

Two-dimensional fingerprint plots and relative contributions of various inter­actions to the Hirshfeld surface of the NIC cocrystal mol­ecule.

Figure 6

Two-dimensional fingerprint plots and relative contributions of various inter­actions to the Hirshfeld surface of the pure NIC mol­ecule.

Figure 7

Two-dimensional fingerprint plots and relative contributions of various inter­actions to the Hirshfeld surface of the CNBA cocrystal mol­ecule.

Figure 8

Two-dimensional fingerprint plots and relative contributions of various inter­actions to the Hirshfeld surface of the pure CNBA mol­ecule

Database survey

A search for the title cocrystal in the Cambridge Structural Database (CSD, Version 5.40, update of February 2019; Groom et al., 2016 ▸) found no hits. However, searches for NIC and CNBA gave 237 and 9 hits, respectively. A search for the NIC mol­ecule showed that the N atom on the phenyl ring forms strong O—H⋯N hydrogen bonds with a carboxyl H atom in the most of the cocrystals [ABULIU (Lou & Hu, 2011 ▸), BICQAH (Aitipamula et al., 2013 ▸), BICQEL (Aitipamula et al., 2013 ▸), BOBQUG (Zhang et al., 2013 ▸), CUYXUQ (Lemmerer & Bernstein, 2010 ▸), DINRUP (Lemmerer et al., 2013 ▸), DINSEA (Lemmerer et al., 2013 ▸), EDAPOQ (Orola & Veidis, 2009 ▸) etc]. For the CNBA search, two structures were found similar to the title com­pound where strong hydrogen bonding is formed by the carboxyl H atom with a pyridine N atom [AJIWIA (Gotoh & Ishida, 2009 ▸) and OCAZAT (Ishida et al., 2001 ▸)]. AJIWIA also shows halogen bonds through C—O⋯Cl bonding and forms a dimer through C—H⋯O hydrogen bonding.

Synthesis and crystallization

All the chemicals used for the synthesis were purchased from Alfa Aesar and used without further purification. A stock solution was prepared from an equimolar mixture of 2-chloro-5 nitro­benzoic acid (82.44 mg, 0.409 mmol) and nicotinamide (50 mg, 0.409 mmol) in a minimum amount of ethanol and made up to a volume of 10 ml. Ten different combinations of the mixture were prepared using ethanol–hexane as the solvent mixture over the ratio range 1:1 to 1:10. The mixture was kept in a 5 ml beaker and covered with parafilm, with four to five small holes in it. These solutions were allowed to evaporate slowly at room temperature (27 °C) over several days to obtain single crystals. After a few days, colourless crystals were obtained from ethanol–hexane solutions with concentration ratios of 1:10, 1:2 and 1:4. The melting point of the obtained crystal was 159.7 °C.

Refinement

Crystal data, data collection, and structure refinement details are summarized in Table 2 ▸. All H atoms were found in a difference Fourier maps and were refind freely.

Table 2

Experimental details

Crystal data
Chemical formula	C7H4ClNO4·C6H6N2O
M r	323.69
Crystal system, space group	Monoclinic, P21/c
Temperature (K)	123
a, b, c (Å)	7.4897 (1), 26.3607 (5), 7.0623 (1)
β (°)	96.356 (1)
V (Å3)	1385.77 (4)
Z	4
Radiation type	Mo Kα
μ (mm−1)	0.31
Crystal size (mm)	0.28 × 0.22 × 0.15
Data collection
Diffractometer	Bruker Kappa APEXII DUO
Absorption correction	Multi-scan (SADABS; Bruker, 2001 ▸)
T min, T max	0.874, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	29950, 4123, 3316
R int	0.037
(sin θ/λ)max (Å−1)	0.708
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.038, 0.094, 1.08
No. of reflections	4123
No. of parameters	239
H-atom treatment	All H-atom parameters refined
Δρmax, Δρmin (e Å−3)	0.30, −0.26

Computer programs: APEX2 (Bruker, 2012 ▸), SAINT (Bruker, 2012 ▸), SHELXS18 (Sheldrick, 2015 ▸), SHELXL2018 (Sheldrick, 2015 ▸), Mercury (Macrae et al., 2008 ▸), OLEX2 (Dolomanov et al., 2009 ▸) and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989019013859/eb2025sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989019013859/eb2025Isup2.hkl

CCDC references: 1958621, 1958621

Additional supporting information: crystallographic information; 3D view; checkCIF report

C7H4ClNO4·C6H6N2O	Dx = 1.551 Mg m−3
Mr = 323.69	Melting point: 159.7 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.4897 (1) Å	Cell parameters from 4123 reflections
b = 26.3607 (5) Å	θ = 1.5–30.2°
c = 7.0623 (1) Å	µ = 0.31 mm−1
β = 96.356 (1)°	T = 123 K
V = 1385.77 (4) Å3	Block, colorless
Z = 4	0.28 × 0.22 × 0.15 mm
F(000) = 664

Bruker Kappa APEXII DUO diffractometer	4123 independent reflections
Radiation source: fine-focus sealed tube	3316 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω scans	θmax = 30.2°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.874, Tmax = 0.908	k = −37→37
29950 measured reflections	l = −9→9

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	All H-atom parameters refined
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0394P)2 + 0.4303P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
4123 reflections	Δρmax = 0.30 e Å−3
239 parameters	Δρmin = −0.26 e Å−3

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. Single-crystal X-ray diffraction data were collected on a Bruker KAPPA APEX II DUO diffractometer using graphite-monochromated Mo-Kα radiation (λ = 0.71073Å)(Bruker, 2012). The data collection was performed at 153 (2) K. The temperature was monitored by an Oxford Cryostream cooling system (Oxford Cryostat). the program SAINT (Bruker, 2012) were used for cell refinement and data reduction. The data were scaled and absorption correction performed using SADABS(Bruker, 2001). The structure was solved by direct methods using SHELXS-18(Sheldrick, 2015) and refined by full-matrix least-squares methods based on F2 using SHELXL-2018/3(Sheldrick, 2015). The computing , Mercury(Macrae et al., 2008) and PLATON (Spek, 2009) were used for molecular graphics and molecular interactions. All non-hydrogen atoms were refined anisotropically.

	x	y	z	Uiso*/Ueq
Cl1	−0.18141 (5)	0.18331 (2)	0.33099 (6)	0.04137 (12)
O2	0.39368 (12)	0.16413 (3)	0.29015 (14)	0.0267 (2)
O1	0.87918 (13)	0.45197 (3)	1.35865 (13)	0.0268 (2)
O5	0.29333 (16)	0.39338 (4)	0.38136 (16)	0.0381 (3)
O3	0.16833 (14)	0.13103 (3)	0.43221 (14)	0.0308 (2)
O4	0.50015 (15)	0.34087 (4)	0.32242 (18)	0.0417 (3)
N1	0.87836 (15)	0.53606 (4)	1.29452 (16)	0.0226 (2)
N2	0.57395 (14)	0.41744 (4)	0.85619 (15)	0.0208 (2)
N3	0.34615 (16)	0.35059 (4)	0.35149 (16)	0.0262 (2)
C6	0.75383 (15)	0.50921 (4)	0.89924 (17)	0.0189 (2)
C1	0.83945 (15)	0.48801 (4)	1.24921 (17)	0.0193 (2)
C2	0.74506 (15)	0.47734 (4)	1.05512 (16)	0.0172 (2)
C12	0.21719 (17)	0.30889 (4)	0.35036 (17)	0.0209 (2)
C4	0.59051 (17)	0.44720 (5)	0.70484 (18)	0.0221 (2)
C13	0.28144 (16)	0.25993 (4)	0.35032 (17)	0.0193 (2)
C5	0.67736 (17)	0.49327 (5)	0.72106 (18)	0.0217 (2)
C9	−0.02066 (17)	0.23039 (5)	0.34499 (19)	0.0243 (3)
C3	0.65244 (16)	0.43172 (4)	1.02733 (17)	0.0201 (2)
C8	0.16239 (16)	0.21927 (4)	0.35036 (16)	0.0191 (2)
C10	−0.08225 (18)	0.28024 (5)	0.3432 (2)	0.0291 (3)
C7	0.24078 (17)	0.16659 (4)	0.36051 (17)	0.0205 (2)
C11	0.03681 (19)	0.32024 (5)	0.34746 (19)	0.0261 (3)
H3	0.639 (2)	0.4084 (6)	1.134 (2)	0.022 (4)*
H6	0.813 (2)	0.5415 (6)	0.909 (2)	0.022 (4)*
H13	0.404 (2)	0.2537 (6)	0.352 (2)	0.028 (4)*
H4	0.540 (2)	0.4339 (6)	0.581 (2)	0.025 (4)*
H5	0.691 (2)	0.5138 (6)	0.612 (2)	0.026 (4)*
H1A	0.947 (2)	0.5426 (6)	1.405 (3)	0.035 (4)*
H1B	0.850 (2)	0.5613 (7)	1.216 (3)	0.038 (5)*
H11	−0.006 (2)	0.3550 (7)	0.346 (3)	0.040 (5)*
H10	−0.208 (3)	0.2870 (7)	0.338 (3)	0.042 (5)*
H2	0.462 (3)	0.1292 (9)	0.326 (3)	0.074 (7)*

	U11	U22	U33	U12	U13	U23
Cl1	0.02685 (18)	0.0403 (2)	0.0562 (3)	−0.01523 (14)	0.00135 (15)	0.00272 (16)
O2	0.0251 (5)	0.0190 (4)	0.0362 (5)	0.0037 (3)	0.0040 (4)	0.0050 (4)
O1	0.0362 (5)	0.0207 (4)	0.0216 (5)	−0.0011 (4)	−0.0050 (4)	0.0024 (3)
O5	0.0529 (7)	0.0147 (4)	0.0430 (6)	−0.0008 (4)	−0.0109 (5)	−0.0029 (4)
O3	0.0424 (6)	0.0172 (4)	0.0346 (5)	−0.0037 (4)	0.0115 (4)	0.0017 (4)
O4	0.0345 (6)	0.0268 (5)	0.0654 (8)	−0.0094 (4)	0.0126 (5)	0.0039 (5)
N1	0.0265 (5)	0.0186 (5)	0.0213 (5)	0.0006 (4)	−0.0040 (4)	−0.0017 (4)
N2	0.0211 (5)	0.0163 (5)	0.0243 (5)	−0.0016 (4)	−0.0008 (4)	−0.0014 (4)
N3	0.0357 (6)	0.0165 (5)	0.0253 (6)	−0.0031 (4)	−0.0022 (4)	0.0021 (4)
C6	0.0196 (5)	0.0151 (5)	0.0220 (6)	−0.0004 (4)	0.0022 (4)	−0.0009 (4)
C1	0.0187 (5)	0.0192 (6)	0.0200 (6)	0.0007 (4)	0.0023 (4)	−0.0015 (4)
C2	0.0167 (5)	0.0164 (5)	0.0184 (5)	0.0018 (4)	0.0015 (4)	−0.0014 (4)
C12	0.0275 (6)	0.0164 (5)	0.0184 (6)	−0.0018 (4)	0.0006 (4)	0.0000 (4)
C4	0.0247 (6)	0.0197 (6)	0.0207 (6)	0.0010 (5)	−0.0022 (5)	−0.0025 (4)
C13	0.0209 (5)	0.0183 (5)	0.0186 (6)	−0.0003 (4)	0.0011 (4)	0.0004 (4)
C5	0.0268 (6)	0.0184 (6)	0.0194 (6)	0.0004 (4)	0.0006 (5)	0.0017 (4)
C9	0.0216 (6)	0.0256 (6)	0.0257 (6)	−0.0044 (5)	0.0025 (5)	0.0000 (5)
C3	0.0216 (5)	0.0173 (5)	0.0212 (6)	−0.0002 (4)	0.0015 (4)	0.0001 (4)
C8	0.0216 (5)	0.0177 (5)	0.0177 (6)	−0.0017 (4)	0.0012 (4)	−0.0002 (4)
C10	0.0217 (6)	0.0320 (7)	0.0335 (7)	0.0045 (5)	0.0027 (5)	0.0004 (5)
C7	0.0266 (6)	0.0167 (5)	0.0174 (6)	−0.0019 (4)	−0.0011 (4)	−0.0008 (4)
C11	0.0305 (7)	0.0218 (6)	0.0255 (7)	0.0061 (5)	0.0010 (5)	−0.0004 (5)

Cl1—C9	1.7244 (13)	C1—C2	1.4977 (16)
O2—C7	1.2994 (15)	C2—C3	1.3913 (16)
O2—H2	1.07 (2)	C12—C13	1.3774 (16)
O1—C1	1.2399 (14)	C12—C11	1.3816 (18)
O5—N3	1.2215 (15)	C4—C5	1.3766 (17)
O3—C7	1.2208 (14)	C4—H4	0.977 (16)
O4—N3	1.2209 (16)	C13—C8	1.3941 (16)
N1—C1	1.3307 (16)	C13—H13	0.932 (16)
N1—H1A	0.901 (19)	C5—H5	0.957 (16)
N1—H1B	0.876 (18)	C9—C10	1.3921 (19)
N2—C3	1.3383 (16)	C9—C8	1.3984 (17)
N2—C4	1.3426 (16)	C3—H3	0.984 (15)
N3—C12	1.4626 (16)	C8—C7	1.5064 (16)
C6—C5	1.3887 (17)	C10—C11	1.379 (2)
C6—C2	1.3922 (16)	C10—H10	0.955 (18)
C6—H6	0.959 (15)	C11—H11	0.971 (18)
C7—O2—H2	111.9 (13)	C12—C13—H13	120.6 (9)
C1—N1—H1A	118.6 (11)	C8—C13—H13	119.6 (9)
C1—N1—H1B	122.7 (12)	C4—C5—C6	119.08 (11)
H1A—N1—H1B	118.4 (16)	C4—C5—H5	121.5 (9)
C3—N2—C4	118.98 (10)	C6—C5—H5	119.4 (9)
O4—N3—O5	123.56 (12)	C10—C9—C8	121.40 (11)
O4—N3—C12	118.49 (11)	C10—C9—Cl1	116.76 (10)
O5—N3—C12	117.95 (12)	C8—C9—Cl1	121.80 (10)
C5—C6—C2	118.89 (11)	N2—C3—C2	122.20 (11)
C5—C6—H6	118.5 (9)	N2—C3—H3	116.1 (9)
C2—C6—H6	122.6 (9)	C2—C3—H3	121.7 (9)
O1—C1—N1	123.25 (11)	C13—C8—C9	117.65 (11)
O1—C1—C2	118.88 (10)	C13—C8—C7	117.57 (10)
N1—C1—C2	117.87 (11)	C9—C8—C7	124.77 (11)
C3—C2—C6	118.46 (11)	C11—C10—C9	120.57 (12)
C3—C2—C1	117.96 (10)	C11—C10—H10	119.3 (11)
C6—C2—C1	123.47 (10)	C9—C10—H10	120.1 (11)
C13—C12—C11	122.95 (11)	O3—C7—O2	124.84 (11)
C13—C12—N3	118.27 (11)	O3—C7—C8	122.60 (11)
C11—C12—N3	118.78 (11)	O2—C7—C8	112.54 (10)
N2—C4—C5	122.26 (11)	C10—C11—C12	117.62 (12)
N2—C4—H4	116.2 (9)	C10—C11—H11	120.6 (11)
C5—C4—H4	121.6 (9)	C12—C11—H11	121.8 (11)
C12—C13—C8	119.79 (11)
C5—C6—C2—C3	−2.96 (17)	C1—C2—C3—N2	−175.60 (10)
C5—C6—C2—C1	173.20 (11)	C12—C13—C8—C9	1.77 (17)
O1—C1—C2—C3	21.57 (16)	C12—C13—C8—C7	−176.93 (11)
N1—C1—C2—C3	−159.19 (11)	C10—C9—C8—C13	−1.15 (19)
O1—C1—C2—C6	−154.61 (12)	Cl1—C9—C8—C13	176.29 (9)
N1—C1—C2—C6	24.63 (17)	C10—C9—C8—C7	177.44 (12)
O4—N3—C12—C13	11.29 (17)	Cl1—C9—C8—C7	−5.12 (18)
O5—N3—C12—C13	−168.81 (12)	C8—C9—C10—C11	−0.3 (2)
O4—N3—C12—C11	−168.07 (12)	Cl1—C9—C10—C11	−177.83 (11)
O5—N3—C12—C11	11.83 (17)	C13—C8—C7—O3	151.23 (12)
C3—N2—C4—C5	−3.55 (18)	C9—C8—C7—O3	−27.36 (19)
C11—C12—C13—C8	−1.03 (19)	C13—C8—C7—O2	−26.97 (15)
N3—C12—C13—C8	179.64 (11)	C9—C8—C7—O2	154.44 (12)
N2—C4—C5—C6	1.33 (19)	C9—C10—C11—C12	1.0 (2)
C2—C6—C5—C4	1.97 (17)	C13—C12—C11—C10	−0.4 (2)
C4—N2—C3—C2	2.47 (17)	N3—C12—C11—C10	178.92 (12)
C6—C2—C3—N2	0.78 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.90 (2)	2.005 (19)	2.9004 (15)	171.4 (14)
N1—H1B···O3	0.873 (19)	2.116 (19)	2.9715 (14)	166.6 (16)
O2—H2···N2	1.07 (2)	1.49 (2)	2.5543 (13)	172 (2)
C3—H3···O4	0.986 (15)	2.516 (15)	3.4505 (16)	158.2 (12)
C4—H4···O5	0.979 (14)	2.442 (15)	3.3256 (17)	149.9 (12)
C5—H5···O5	0.956 (15)	2.450 (16)	3.0878 (17)	124.0 (11)
C6—H6···O3	0.959 (15)	2.608 (15)	3.452 (1)	147.0 (11)
C10—H10···O4	0.955 (15)	2.599 (16)	3.5010 (18)	157.6 (15)