Bis(creatininium) 3-nitro­phthalate monohydrate

Thayanithi, V.; Kumar, P.P.; Gunasekaran, B.

doi:10.1107/S2414314616009895

organic compounds

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ISSN: 2414-3146

Volume 1| Part 6| June 2016| x160989

doi:10.1107/S2414314616009895

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Bis(creatininium) 3-nitrophthalate monohydrate

V. Thayanithi,^a P. Praveen Kumar ^a ^* and B. Gunasekaran ^b

^aDepartment of Physics, Presidency college, Chennai 600 005, Tamil Nadu, India, and ^bDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203 Tamil Nadu, India
^*Correspondence e-mail: ppkpresidency@gmail.com, phdguna@gmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 24 May 2016; accepted 17 June 2016; online 24 June 2016)

In the title hydrated molecular salt, 2C₄H₈N₃O⁺·C₈H₃NO₆²⁻·H₂O, the dihedral angles between the benzene ring and the nitro group and the carboxylate groups are 48.0 (2), 55.3 (2) and 60.7 (2)°, respectively. In the crystal, the components are linked by N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds, generating a two-dimensional network parallel to (102).

Keywords: crystal structure; creatininium; phthalate; glomerular filtration rate; hydrogen bonding.

CCDC reference: 1486234

Structure description

Creatinine (systematic name: 2-imino-1-methylimidazolidin-4-one) and its derivatives display a range of biological activity. In particular, creatinine is an indicator of renal function. In understanding renal dysfunction, the determination of creatinine is more important than that of urea (Sharma et al., 2004 ). Creatinine clearance is used to determine the glomerular filtration rate (GFR) of the kidneys (Mădăraş & Buck, 1996 ) and various disease states in biological fluids can be indicated by an abnormal level of creatinine (Narayanan & Appleton, 1980 ). We report here the structure of the protonated creatinine derivative bis-creatininium 3-nitrophthalate that crystallizes as a monohydrate.

The asymmetric unit of the title compound comprises two protonated creatinine cations, one doubly deprotonated 3-nitrophthalic acid anion and a water molecule of crystallization (Fig. 1). The geometric parameters of the title molecule agree well with those reported for similar similar structures (Jahubar Ali et al., 2011 , 2012 ). The packing features N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds, which generate a two-dimensional network parallel to (102) (Table 1, Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9W—H9WA⋯O2	0.86 (1)	1.94 (2)	2.7856 (18)	168 (2)
O9W—H9WB⋯O8ⁱ	0.85 (1)	2.16 (2)	2.9241 (18)	149 (2)
N2—H2A⋯O3ⁱⁱ	0.86	2.00	2.7899 (17)	152
N2—H2B⋯O2ⁱⁱⁱ	0.86	1.95	2.8000 (17)	168
N3—H3A⋯O1ⁱⁱⁱ	0.86	1.77	2.6275 (15)	177
N5—H5⋯O4^iv	0.86	1.84	2.6836 (16)	166
N6—H6A⋯O9W^v	0.86	1.96	2.7952 (17)	163
N6—H6B⋯O3^iv	0.86	1.94	2.7900 (16)	171
C4—H4⋯O5ⁱ	0.93	2.59	3.2071 (19)	124
C9—H9B⋯O6^vi	0.97	2.47	3.212 (2)	133
Symmetry codes: (i) -x, -y, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (vi) -x+1, -y, -z+1.

Figure 1
The molecular structure with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Figure 2
The packing, viewed down the a axis. Hydrogen bonds are shown as dashed lines.

Synthesis and crystallization

Creatinine and 3-nitrophthalic acid in 2:1 molar ratio were dissolved in deionized water. The solution was stirred well, filtered and kept in a dust-free environment. Crystals were obtained from the mother solution after 10 d (yield 95%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	2C₄H₈N₃O⁺·C₈H₃NO₆²⁻·H₂O
M_r	455.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.6682 (3), 16.5504 (6), 16.2358 (7)
β (°)	93.775 (1)
V (Å³)	2056.04 (14)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.12
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996 )
T_min, T_max	0.964, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	30566, 3620, 3202
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.097, 1.04
No. of reflections	3620
No. of parameters	299
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.19
Computer programs: APEX2 and SAINT (Bruker, 2008 ), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1486234

Crystal structure: contains datablocks C3NP, I. DOI: 10.1107/S2414314616009895/sj4041sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616009895/sj4041Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616009895/sj4041Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Bis(2-amino-1-methyl-4-oxo-1H-imidazol-3-ium) 3-nitrobenzene-1,2-dioate monohydrate top

Crystal data top

2C₄H₈N₃O⁺·C₈H₃NO₆²⁻·H₂O	F(000) = 952
M_r = 455.40	D_x = 1.471 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3032 reflections
a = 7.6682 (3) Å	θ = 2.5–25.0°
b = 16.5504 (6) Å	µ = 0.12 mm⁻¹
c = 16.2358 (7) Å	T = 295 K
β = 93.775 (1)°	Block, colourless
V = 2056.04 (14) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3620 independent reflections
Radiation source: fine-focus sealed tube	3202 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 0 pixels mm^-1	θ_max = 25.0°, θ_min = 2.5°
ω and φ scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −19→19
T_min = 0.964, T_max = 0.975	l = −19→19
30566 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0511P)² + 0.6212P] where P = (F_o² + 2F_c²)/3
3620 reflections	(Δ/σ)_max < 0.001
299 parameters	Δρ_max = 0.23 e Å⁻³
3 restraints	Δρ_min = −0.19 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O4	0.31739 (13)	0.24338 (6)	0.37689 (7)	0.0426 (3)
O2	−0.20496 (15)	0.39851 (6)	0.44152 (7)	0.0468 (3)
O1	−0.05094 (16)	0.36012 (6)	0.33692 (7)	0.0500 (3)
O7	−0.12906 (18)	−0.00022 (8)	0.32383 (8)	0.0623 (4)
O3	0.26695 (14)	0.34371 (6)	0.46389 (7)	0.0455 (3)
O8	0.37908 (18)	−0.23485 (8)	0.30455 (8)	0.0650 (4)
N4	0.04747 (17)	0.14441 (7)	0.19650 (8)	0.0411 (3)
N5	0.50199 (16)	−0.15212 (7)	0.21091 (8)	0.0382 (3)
H5	0.5431	−0.1882	0.1794	0.046*
C1	−0.09432 (17)	0.26573 (8)	0.44182 (8)	0.0292 (3)
C5	0.08351 (17)	0.15554 (8)	0.48841 (8)	0.0306 (3)
O6	0.36494 (17)	0.16305 (9)	0.54522 (9)	0.0698 (4)
N1	0.25658 (17)	0.12099 (8)	0.50719 (9)	0.0455 (3)
N7	0.43615 (16)	−0.03075 (8)	0.25712 (7)	0.0392 (3)
N2	0.15811 (18)	0.06240 (8)	0.09368 (8)	0.0446 (3)
H2A	0.1982	0.1028	0.0675	0.054*
H2B	0.1711	0.0141	0.0755	0.054*
C6	0.07245 (17)	0.23258 (7)	0.45540 (7)	0.0275 (3)
N6	0.59974 (16)	−0.04045 (7)	0.13985 (8)	0.0406 (3)
H6A	0.6065	0.0111	0.1343	0.049*
H6B	0.6479	−0.0718	0.1057	0.049*
N3	0.01716 (15)	0.01224 (7)	0.20550 (7)	0.0367 (3)
H3A	0.0275	−0.0380	0.1932	0.044*
O5	0.28472 (18)	0.05264 (8)	0.48399 (11)	0.0811 (5)
C2	−0.24056 (18)	0.22093 (9)	0.45977 (9)	0.0357 (3)
H2	−0.3512	0.2436	0.4513	0.043*
C14	0.07773 (18)	0.07435 (8)	0.16086 (8)	0.0341 (3)
C4	−0.05969 (19)	0.11000 (8)	0.50609 (9)	0.0364 (3)
H4	−0.0464	0.0584	0.5282	0.044*
C8	0.23328 (17)	0.27727 (8)	0.43044 (8)	0.0314 (3)
C3	−0.22333 (19)	0.14322 (9)	0.49004 (9)	0.0387 (3)
H3	−0.3224	0.1132	0.4997	0.046*
C7	−0.11757 (18)	0.34859 (8)	0.40421 (9)	0.0338 (3)
C9	0.3674 (2)	−0.08763 (10)	0.31486 (9)	0.0468 (4)
H9A	0.2420	−0.0815	0.3172	0.056*
H9B	0.4229	−0.0807	0.3698	0.056*
C11	0.51691 (17)	−0.07093 (8)	0.19967 (8)	0.0333 (3)
C10	0.4126 (2)	−0.16844 (10)	0.27923 (10)	0.0445 (4)
C13	−0.0626 (2)	0.04049 (10)	0.27279 (9)	0.0423 (4)
C15	0.4564 (2)	0.05471 (10)	0.27549 (11)	0.0492 (4)
H15A	0.5508	0.0621	0.3166	0.074*
H15B	0.3502	0.0752	0.2958	0.074*
H15C	0.4814	0.0833	0.2262	0.074*
C12	−0.0482 (2)	0.13135 (10)	0.26946 (10)	0.0480 (4)
H12A	−0.1627	0.1564	0.2638	0.058*
H12B	0.0155	0.1524	0.3185	0.058*
C16	0.0946 (3)	0.22366 (10)	0.16828 (11)	0.0602 (5)
H16A	0.1949	0.2195	0.1361	0.090*
H16B	0.1217	0.2580	0.2150	0.090*
H16C	−0.0013	0.2462	0.1349	0.090*
O9W	−0.3299 (2)	0.38052 (7)	0.59774 (8)	0.0656 (4)
H9WA	−0.302 (3)	0.3802 (13)	0.5476 (7)	0.090 (8)*
H9WB	−0.358 (3)	0.3319 (8)	0.6078 (13)	0.100 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0439 (6)	0.0355 (5)	0.0506 (6)	−0.0020 (4)	0.0200 (5)	−0.0028 (5)
O2	0.0563 (7)	0.0333 (6)	0.0528 (6)	0.0121 (5)	0.0187 (5)	0.0086 (5)
O1	0.0735 (8)	0.0375 (6)	0.0411 (6)	0.0100 (5)	0.0192 (5)	0.0112 (5)
O7	0.0802 (9)	0.0622 (8)	0.0472 (7)	0.0035 (7)	0.0254 (6)	0.0062 (6)
O3	0.0558 (7)	0.0379 (6)	0.0445 (6)	−0.0188 (5)	0.0165 (5)	−0.0095 (5)
O8	0.0799 (9)	0.0548 (8)	0.0619 (8)	−0.0041 (6)	0.0164 (7)	0.0222 (6)
N4	0.0553 (8)	0.0328 (6)	0.0353 (7)	0.0030 (5)	0.0038 (6)	−0.0046 (5)
N5	0.0414 (7)	0.0341 (7)	0.0400 (7)	0.0036 (5)	0.0093 (5)	0.0023 (5)
C1	0.0342 (7)	0.0271 (7)	0.0267 (6)	0.0014 (5)	0.0042 (5)	0.0002 (5)
C5	0.0335 (7)	0.0272 (7)	0.0317 (7)	0.0031 (5)	0.0064 (5)	0.0003 (5)
O6	0.0455 (7)	0.0771 (9)	0.0840 (10)	0.0088 (7)	−0.0164 (7)	0.0045 (8)
N1	0.0419 (7)	0.0367 (7)	0.0590 (8)	0.0083 (6)	0.0114 (6)	0.0131 (6)
N7	0.0424 (7)	0.0408 (7)	0.0352 (6)	0.0059 (5)	0.0086 (5)	−0.0018 (5)
N2	0.0640 (9)	0.0340 (7)	0.0374 (7)	−0.0006 (6)	0.0153 (6)	−0.0025 (5)
C6	0.0337 (7)	0.0244 (6)	0.0247 (6)	−0.0016 (5)	0.0049 (5)	−0.0023 (5)
N6	0.0464 (7)	0.0322 (6)	0.0452 (7)	−0.0007 (5)	0.0177 (6)	−0.0027 (5)
N3	0.0438 (7)	0.0333 (6)	0.0334 (6)	0.0011 (5)	0.0052 (5)	−0.0034 (5)
O5	0.0613 (8)	0.0378 (7)	0.1471 (15)	0.0172 (6)	0.0299 (9)	0.0047 (8)
C2	0.0308 (7)	0.0379 (8)	0.0388 (8)	0.0019 (6)	0.0050 (6)	0.0017 (6)
C14	0.0377 (7)	0.0343 (7)	0.0298 (7)	0.0011 (6)	−0.0026 (6)	−0.0021 (6)
C4	0.0458 (8)	0.0231 (6)	0.0418 (8)	−0.0001 (6)	0.0133 (6)	0.0031 (6)
C8	0.0330 (7)	0.0298 (7)	0.0317 (7)	−0.0012 (5)	0.0037 (5)	0.0018 (5)
C3	0.0374 (8)	0.0354 (8)	0.0445 (8)	−0.0078 (6)	0.0130 (6)	0.0005 (6)
C7	0.0357 (7)	0.0311 (7)	0.0344 (7)	0.0015 (6)	0.0023 (6)	0.0048 (6)
C9	0.0486 (9)	0.0593 (10)	0.0334 (8)	0.0110 (8)	0.0093 (7)	0.0081 (7)
C11	0.0293 (7)	0.0360 (7)	0.0347 (7)	0.0029 (5)	0.0020 (5)	−0.0006 (6)
C10	0.0438 (9)	0.0494 (9)	0.0404 (8)	0.0025 (7)	0.0039 (7)	0.0123 (7)
C13	0.0460 (8)	0.0488 (9)	0.0322 (8)	0.0065 (7)	0.0036 (6)	−0.0006 (7)
C15	0.0487 (9)	0.0476 (9)	0.0517 (9)	0.0067 (7)	0.0064 (7)	−0.0135 (8)
C12	0.0629 (10)	0.0468 (9)	0.0350 (8)	0.0098 (8)	0.0073 (7)	−0.0077 (7)
C16	0.0952 (15)	0.0345 (9)	0.0512 (10)	−0.0020 (9)	0.0069 (9)	−0.0022 (7)
O9W	0.1076 (11)	0.0374 (7)	0.0546 (8)	0.0013 (7)	0.0266 (8)	−0.0016 (6)

Geometric parameters (Å, º) top

O4—C8	1.2491 (16)	C6—C8	1.5159 (18)
O2—C7	1.2458 (17)	N6—C11	1.2970 (18)
O1—C7	1.2508 (17)	N6—H6A	0.8600
O7—C13	1.2065 (19)	N6—H6B	0.8600
O3—C8	1.2459 (17)	N3—C14	1.3573 (19)
O8—C10	1.2072 (19)	N3—C13	1.3690 (19)
N4—C14	1.3232 (18)	N3—H3A	0.8600
N4—C16	1.443 (2)	C2—C3	1.380 (2)
N4—C12	1.450 (2)	C2—H2	0.9300
N5—C11	1.3617 (18)	C4—C3	1.379 (2)
N5—C10	1.369 (2)	C4—H4	0.9300
N5—H5	0.8600	C3—H3	0.9300
C1—C2	1.3911 (19)	C9—C10	1.507 (2)
C1—C6	1.3957 (18)	C9—H9A	0.9700
C1—C7	1.5070 (18)	C9—H9B	0.9700
C5—C4	1.3775 (19)	C13—C12	1.509 (2)
C5—C6	1.3836 (18)	C15—H15A	0.9600
C5—N1	1.4587 (18)	C15—H15B	0.9600
O6—N1	1.2200 (19)	C15—H15C	0.9600
N1—O5	1.2161 (18)	C12—H12A	0.9700
N7—C11	1.3311 (18)	C12—H12B	0.9700
N7—C15	1.452 (2)	C16—H16A	0.9600
N7—C9	1.452 (2)	C16—H16B	0.9600
N2—C14	1.3028 (19)	C16—H16C	0.9600
N2—H2A	0.8600	O9W—H9WA	0.855 (9)
N2—H2B	0.8600	O9W—H9WB	0.852 (9)

C14—N4—C16	127.06 (14)	O4—C8—C6	115.68 (12)
C14—N4—C12	109.84 (12)	C4—C3—C2	120.23 (13)
C16—N4—C12	123.07 (13)	C4—C3—H3	119.9
C11—N5—C10	110.75 (12)	C2—C3—H3	119.9
C11—N5—H5	124.6	O2—C7—O1	125.96 (13)
C10—N5—H5	124.6	O2—C7—C1	117.35 (12)
C2—C1—C6	120.02 (12)	O1—C7—C1	116.65 (12)
C2—C1—C7	119.63 (12)	N7—C9—C10	103.02 (12)
C6—C1—C7	120.29 (11)	N7—C9—H9A	111.2
C4—C5—C6	123.75 (12)	C10—C9—H9A	111.2
C4—C5—N1	117.95 (12)	N7—C9—H9B	111.2
C6—C5—N1	118.29 (12)	C10—C9—H9B	111.2
O5—N1—O6	123.96 (15)	H9A—C9—H9B	109.1
O5—N1—C5	118.51 (14)	N6—C11—N7	127.13 (13)
O6—N1—C5	117.52 (13)	N6—C11—N5	122.26 (13)
C11—N7—C15	125.62 (13)	N7—C11—N5	110.61 (12)
C11—N7—C9	109.51 (12)	O8—C10—N5	125.80 (16)
C15—N7—C9	122.51 (13)	O8—C10—C9	128.18 (15)
C14—N2—H2A	120.0	N5—C10—C9	106.03 (13)
C14—N2—H2B	120.0	O7—C13—N3	126.04 (15)
H2A—N2—H2B	120.0	O7—C13—C12	128.05 (14)
C5—C6—C1	117.10 (12)	N3—C13—C12	105.90 (13)
C5—C6—C8	121.54 (12)	N7—C15—H15A	109.5
C1—C6—C8	121.27 (11)	N7—C15—H15B	109.5
C11—N6—H6A	120.0	H15A—C15—H15B	109.5
C11—N6—H6B	120.0	N7—C15—H15C	109.5
H6A—N6—H6B	120.0	H15A—C15—H15C	109.5
C14—N3—C13	110.74 (12)	H15B—C15—H15C	109.5
C14—N3—H3A	124.6	N4—C12—C13	102.71 (12)
C13—N3—H3A	124.6	N4—C12—H12A	111.2
C3—C2—C1	120.78 (13)	C13—C12—H12A	111.2
C3—C2—H2	119.6	N4—C12—H12B	111.2
C1—C2—H2	119.6	C13—C12—H12B	111.2
N2—C14—N4	127.26 (14)	H12A—C12—H12B	109.1
N2—C14—N3	121.98 (13)	N4—C16—H16A	109.5
N4—C14—N3	110.74 (12)	N4—C16—H16B	109.5
C5—C4—C3	118.06 (12)	H16A—C16—H16B	109.5
C5—C4—H4	121.0	N4—C16—H16C	109.5
C3—C4—H4	121.0	H16A—C16—H16C	109.5
O3—C8—O4	126.73 (13)	H16B—C16—H16C	109.5
O3—C8—C6	117.58 (12)	H9WA—O9W—H9WB	105.1 (14)

C4—C5—N1—O5	49.1 (2)	C1—C6—C8—O4	−117.14 (14)
C6—C5—N1—O5	−132.09 (15)	C5—C4—C3—C2	−2.1 (2)
C4—C5—N1—O6	−131.17 (15)	C1—C2—C3—C4	2.6 (2)
C6—C5—N1—O6	47.61 (19)	C2—C1—C7—O2	55.03 (18)
C4—C5—C6—C1	1.80 (19)	C6—C1—C7—O2	−127.68 (14)
N1—C5—C6—C1	−176.91 (12)	C2—C1—C7—O1	−123.06 (15)
C4—C5—C6—C8	−174.78 (13)	C6—C1—C7—O1	54.23 (18)
N1—C5—C6—C8	6.51 (19)	C11—N7—C9—C10	−2.97 (16)
C2—C1—C6—C5	−1.31 (19)	C15—N7—C9—C10	−166.41 (14)
C7—C1—C6—C5	−178.58 (12)	C15—N7—C11—N6	−14.4 (2)
C2—C1—C6—C8	175.28 (12)	C9—N7—C11—N6	−177.21 (14)
C7—C1—C6—C8	−2.00 (18)	C15—N7—C11—N5	165.78 (14)
C6—C1—C2—C3	−0.8 (2)	C9—N7—C11—N5	2.98 (16)
C7—C1—C2—C3	176.46 (13)	C10—N5—C11—N6	178.51 (13)
C16—N4—C14—N2	1.0 (3)	C10—N5—C11—N7	−1.67 (17)
C12—N4—C14—N2	179.12 (15)	C11—N5—C10—O8	179.93 (16)
C16—N4—C14—N3	179.08 (16)	C11—N5—C10—C9	−0.30 (17)
C12—N4—C14—N3	−2.76 (17)	N7—C9—C10—O8	−178.31 (17)
C13—N3—C14—N2	−179.73 (14)	N7—C9—C10—N5	1.93 (16)
C13—N3—C14—N4	2.03 (16)	C14—N3—C13—O7	179.98 (16)
C6—C5—C4—C3	−0.1 (2)	C14—N3—C13—C12	−0.45 (16)
N1—C5—C4—C3	178.63 (13)	C14—N4—C12—C13	2.32 (17)
C5—C6—C8—O3	−121.68 (14)	C16—N4—C12—C13	−179.43 (15)
C1—C6—C8—O3	61.89 (17)	O7—C13—C12—N4	178.47 (16)
C5—C6—C8—O4	59.29 (17)	N3—C13—C12—N4	−1.08 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9W—H9WA···O2	0.86 (1)	1.94 (2)	2.7856 (18)	168 (2)
O9W—H9WB···O8ⁱ	0.85 (1)	2.16 (2)	2.9241 (18)	149 (2)
N2—H2A···O3ⁱⁱ	0.86	2.00	2.7899 (17)	152
N2—H2B···O2ⁱⁱⁱ	0.86	1.95	2.8000 (17)	168
N3—H3A···O1ⁱⁱⁱ	0.86	1.77	2.6275 (15)	177
N5—H5···O4^iv	0.86	1.84	2.6836 (16)	166
N6—H6A···O9W^v	0.86	1.96	2.7952 (17)	163
N6—H6B···O3^iv	0.86	1.94	2.7900 (16)	171
C4—H4···O5ⁱ	0.93	2.59	3.2071 (19)	124
C9—H9B···O6^vi	0.97	2.47	3.212 (2)	133

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

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