1,3,7-Trimethylxanthenium 2,4,6-trinitro­phenolate

Chandramohan, A.; Gayathri, D.; Velmurugan, D.; Ravikumar, K.; Kandhaswamy, M.A.

doi:10.1107/S1600536807017825

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1,3,7-Trimethylxanthenium 2,4,6-trinitrophenolate

A. Chandramohan, D. Gayathri, D. Velmurugan, K. Ravikumar and M. A. Kandhaswamy

The caffeinium and picrate ions in the title compound, C₈H₁₁N₄O₂⁺·C₆H₂N₃O₇⁻, are connected by intermolecular N—H

O and C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017825/bt2324sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017825/bt2324Isup2.hkl Contains datablock I

CCDC reference: 646760

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R factor = 0.046
wR factor = 0.140
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N5
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N7
PLAT432_ALERT_2_B Short Inter X...Y Contact  O9A    ..  C5      ..       2.91 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C5     ..  O9B     ..       2.78 Ang.

Alert level C
PLAT213_ALERT_2_C Atom O8B     has ADP max/min Ratio .............       3.70 prola
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.01 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.14
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.17
PLAT301_ALERT_3_C Main Residue  Disorder .........................      12.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O4A    ..  C1      ..       2.96 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      40.70 Deg.
              O5B  -N5   -O5A     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.90 Deg.
              O8B  -N7   -O8A     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      39.20 Deg.
              O9B  -N7   -O9A     1.555   1.555   1.555

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1,3,7-Trimethylxanthenium 2,4,6-trinitrophenolate top

Crystal data top

C₈H₁₁N₄O₂⁺·C₆H₂N₃O₇⁻	F(000) = 872
M_r = 423.31	D_x = 1.622 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1985 reflections
a = 8.2996 (10) Å	θ = 1.8–25.0°
b = 9.0014 (11) Å	µ = 0.14 mm⁻¹
c = 23.210 (3) Å	T = 293 K
β = 91.474 (2)°	Needle, yellow
V = 1733.4 (4) Å³	0.29 × 0.24 × 0.23 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3243 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 28.0°, θ_min = 1.8°
ω scans	h = −10→10
18720 measured reflections	k = −11→11
4035 independent reflections	l = −30→30

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0721P)² + 0.5266P] where P = (F_o² + 2F_c²)/3
4035 reflections	(Δ/σ)_max = 0.001
312 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.50927 (19)	0.40445 (16)	0.64523 (7)	0.0380 (3)
C2	0.43578 (19)	0.50128 (17)	0.68581 (7)	0.0383 (3)
C3	0.54127 (19)	0.70531 (17)	0.62428 (7)	0.0390 (3)
C4	0.58960 (18)	0.45533 (16)	0.59891 (6)	0.0347 (3)
C5	0.5899 (2)	0.21313 (18)	0.59596 (7)	0.0444 (4)
H5	0.6082	0.1160	0.5842	0.053*
C6	0.4325 (3)	0.14808 (18)	0.68149 (9)	0.0592 (5)
H6A	0.4489	0.0478	0.6688	0.089*
H6B	0.3190	0.1689	0.6819	0.089*
H6C	0.4781	0.1601	0.7196	0.089*
C7	0.3995 (2)	0.76127 (19)	0.71253 (8)	0.0535 (5)
H7A	0.4815	0.8332	0.7218	0.080*
H7B	0.3674	0.7123	0.7471	0.080*
H7C	0.3080	0.8103	0.6950	0.080*
C8	0.6859 (2)	0.65673 (19)	0.53521 (7)	0.0462 (4)
H8A	0.7240	0.5739	0.5133	0.069*
H8B	0.7751	0.7198	0.5459	0.069*
H8C	0.6089	0.7121	0.5123	0.069*
C9	0.85566 (19)	0.29584 (19)	0.42792 (7)	0.0415 (4)
C10	0.94532 (19)	0.37721 (19)	0.38539 (7)	0.0420 (4)
C11	1.04048 (19)	0.3111 (2)	0.34517 (7)	0.0446 (4)
H11	1.0958	0.3690	0.3190	0.054*
C12	1.0536 (2)	0.1578 (2)	0.34382 (7)	0.0454 (4)
C13	0.9721 (2)	0.0694 (2)	0.38226 (7)	0.0457 (4)
H13	0.9801	−0.0335	0.3808	0.055*
C14	0.8794 (2)	0.13749 (19)	0.42257 (7)	0.0437 (4)
N1	0.51082 (17)	0.25090 (14)	0.64210 (6)	0.0427 (3)
N2	0.46319 (16)	0.65074 (13)	0.67221 (6)	0.0399 (3)
N3	0.60930 (15)	0.60230 (14)	0.58734 (5)	0.0375 (3)
N4	0.64046 (16)	0.33490 (14)	0.56826 (6)	0.0401 (3)
H4	0.6946	0.3368	0.5372	0.048*
N5	0.9406 (2)	0.53980 (18)	0.38548 (7)	0.0533 (4)
N6	1.15499 (19)	0.0879 (2)	0.30175 (7)	0.0552 (4)
N7	0.7979 (2)	0.03959 (17)	0.46257 (7)	0.0566 (4)
O1	0.35857 (16)	0.46430 (13)	0.72730 (5)	0.0533 (3)
O2	0.55159 (17)	0.83797 (13)	0.61508 (6)	0.0538 (3)
O3	0.76457 (17)	0.35555 (14)	0.46351 (6)	0.0568 (3)
O4A	0.8235 (3)	0.6022 (2)	0.40339 (12)	0.0729 (6)	0.70
O4B	0.9468 (11)	0.6012 (6)	0.4356 (3)	0.096 (2)	0.30
O5A	1.0489 (4)	0.6048 (4)	0.3619 (2)	0.0921 (12)	0.70
O5B	0.9606 (16)	0.6096 (11)	0.3451 (4)	0.117 (4)	0.30
O6	1.21360 (19)	0.1657 (2)	0.26435 (6)	0.0732 (4)
O7	1.1776 (2)	−0.04606 (19)	0.30544 (7)	0.0761 (5)
O8A	0.7360 (6)	−0.0753 (6)	0.44375 (19)	0.0786 (11)	0.80
O8B	0.799 (3)	−0.083 (2)	0.4517 (12)	0.172 (13)	0.20
O9A	0.8040 (4)	0.0749 (5)	0.51402 (14)	0.0757 (9)	0.80
O9B	0.716 (2)	0.0804 (16)	0.4988 (6)	0.104 (6)	0.20

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0454 (8)	0.0266 (7)	0.0423 (8)	0.0004 (6)	0.0091 (6)	0.0006 (6)
C2	0.0434 (8)	0.0286 (7)	0.0435 (8)	−0.0011 (6)	0.0101 (6)	0.0000 (6)
C3	0.0436 (8)	0.0292 (7)	0.0444 (8)	−0.0004 (6)	0.0074 (6)	0.0017 (6)
C4	0.0372 (7)	0.0303 (7)	0.0367 (7)	0.0001 (6)	0.0039 (6)	−0.0005 (6)
C5	0.0568 (10)	0.0303 (7)	0.0468 (9)	0.0029 (7)	0.0115 (7)	−0.0034 (6)
C6	0.0896 (14)	0.0281 (8)	0.0613 (11)	−0.0053 (8)	0.0297 (10)	0.0026 (7)
C7	0.0694 (12)	0.0309 (8)	0.0616 (11)	0.0015 (8)	0.0287 (9)	−0.0058 (7)
C8	0.0572 (10)	0.0437 (9)	0.0382 (8)	−0.0045 (7)	0.0095 (7)	0.0058 (7)
C9	0.0450 (8)	0.0418 (8)	0.0379 (8)	0.0025 (7)	0.0049 (6)	−0.0009 (6)
C10	0.0417 (8)	0.0412 (8)	0.0432 (8)	−0.0003 (6)	0.0010 (6)	0.0015 (6)
C11	0.0402 (8)	0.0534 (10)	0.0405 (8)	−0.0030 (7)	0.0035 (6)	0.0043 (7)
C12	0.0414 (8)	0.0547 (10)	0.0403 (8)	0.0035 (7)	0.0058 (7)	−0.0048 (7)
C13	0.0510 (9)	0.0426 (9)	0.0438 (8)	0.0056 (7)	0.0047 (7)	−0.0020 (7)
C14	0.0504 (9)	0.0422 (9)	0.0389 (8)	0.0009 (7)	0.0085 (7)	0.0025 (6)
N1	0.0568 (8)	0.0271 (6)	0.0449 (7)	−0.0004 (6)	0.0132 (6)	0.0000 (5)
N2	0.0473 (7)	0.0272 (6)	0.0458 (7)	0.0006 (5)	0.0142 (6)	−0.0017 (5)
N3	0.0441 (7)	0.0293 (6)	0.0395 (6)	−0.0009 (5)	0.0098 (5)	0.0031 (5)
N4	0.0475 (7)	0.0337 (7)	0.0397 (7)	0.0012 (5)	0.0107 (5)	−0.0027 (5)
N5	0.0547 (9)	0.0433 (8)	0.0619 (10)	−0.0032 (7)	0.0043 (7)	0.0039 (7)
N6	0.0499 (8)	0.0653 (11)	0.0511 (8)	0.0051 (7)	0.0129 (7)	−0.0085 (7)
N7	0.0752 (11)	0.0425 (9)	0.0534 (9)	0.0087 (8)	0.0233 (8)	0.0068 (7)
O1	0.0683 (8)	0.0368 (6)	0.0564 (7)	−0.0032 (5)	0.0306 (6)	0.0009 (5)
O2	0.0745 (8)	0.0273 (6)	0.0607 (8)	−0.0013 (5)	0.0203 (6)	0.0036 (5)
O3	0.0744 (9)	0.0462 (7)	0.0511 (7)	0.0084 (6)	0.0242 (6)	−0.0002 (5)
O4A	0.0775 (15)	0.0464 (11)	0.0960 (17)	0.0135 (11)	0.0251 (13)	0.0029 (11)
O4B	0.157 (7)	0.048 (3)	0.085 (4)	−0.017 (4)	0.041 (4)	−0.015 (3)
O5A	0.0746 (18)	0.0543 (15)	0.149 (4)	−0.0135 (15)	0.0337 (19)	0.009 (2)
O5B	0.226 (12)	0.061 (4)	0.064 (4)	−0.022 (7)	−0.004 (6)	0.031 (3)
O6	0.0679 (9)	0.0914 (12)	0.0618 (9)	0.0003 (8)	0.0300 (7)	−0.0014 (8)
O7	0.0818 (10)	0.0650 (10)	0.0826 (10)	0.0169 (8)	0.0263 (8)	−0.0136 (8)
O8A	0.103 (2)	0.0581 (19)	0.0755 (17)	−0.0265 (16)	0.0141 (18)	0.0107 (14)
O8B	0.28 (3)	0.033 (6)	0.21 (2)	−0.017 (13)	0.18 (2)	−0.004 (11)
O9A	0.118 (3)	0.0647 (14)	0.0455 (11)	0.0141 (18)	0.0271 (14)	0.0086 (9)
O9B	0.174 (15)	0.048 (5)	0.094 (11)	−0.004 (9)	0.100 (10)	−0.007 (7)

Geometric parameters (Å, º) top

C1—C4	1.359 (2)	C9—C14	1.445 (2)
C1—N1	1.384 (2)	C9—C10	1.450 (2)
C1—C2	1.431 (2)	C10—C11	1.374 (2)
C2—O1	1.217 (2)	C10—N5	1.464 (2)
C2—N2	1.402 (2)	C11—C12	1.384 (3)
C3—O2	1.217 (2)	C11—H11	0.9300
C3—N2	1.391 (2)	C12—C13	1.385 (2)
C3—N3	1.392 (2)	C12—N6	1.449 (2)
C4—N3	1.361 (2)	C13—C14	1.371 (2)
C4—N4	1.369 (2)	C13—H13	0.9300
C5—N1	1.315 (2)	C14—N7	1.459 (2)
C5—N4	1.343 (2)	N4—H4	0.8600
C5—H5	0.9300	N5—O5B	1.143 (8)
C6—N1	1.465 (2)	N5—O5A	1.214 (4)
C6—H6A	0.9600	N5—O4A	1.206 (3)
C6—H6B	0.9600	N5—O4B	1.287 (6)
C6—H6C	0.9600	N6—O7	1.223 (2)
C7—N2	1.473 (2)	N6—O6	1.226 (2)
C7—H7A	0.9600	N7—O8B	1.13 (2)
C7—H7B	0.9600	N7—O9B	1.156 (12)
C7—H7C	0.9600	N7—O8A	1.230 (5)
C8—N3	1.466 (2)	N7—O9A	1.236 (4)
C8—H8A	0.9600	O4A—O4B	1.251 (9)
C8—H8B	0.9600	O5A—O5B	0.822 (10)
C8—H8C	0.9600	O9A—O9B	0.806 (17)
C9—O3	1.255 (2)

C4—C1—N1	106.83 (13)	C14—C13—H13	120.8
C4—C1—C2	122.78 (14)	C12—C13—H13	120.8
N1—C1—C2	130.34 (14)	C13—C14—C9	125.43 (15)
O1—C2—N2	122.18 (14)	C13—C14—N7	116.23 (15)
O1—C2—C1	126.61 (14)	C9—C14—N7	118.34 (14)
N2—C2—C1	111.21 (13)	C5—N1—C1	107.85 (13)
O2—C3—N2	121.55 (14)	C5—N1—C6	125.71 (14)
O2—C3—N3	120.94 (14)	C1—N1—C6	126.39 (13)
N2—C3—N3	117.51 (13)	C3—N2—C2	126.90 (13)
C1—C4—N3	123.21 (13)	C3—N2—C7	116.85 (13)
C1—C4—N4	107.95 (13)	C2—N2—C7	116.24 (13)
N3—C4—N4	128.83 (13)	C4—N3—C3	118.25 (12)
N1—C5—N4	110.33 (14)	C4—N3—C8	123.01 (13)
N1—C5—H5	124.8	C3—N3—C8	118.51 (13)
N4—C5—H5	124.8	C5—N4—C4	107.04 (13)
N1—C6—H6A	109.5	C5—N4—H4	126.5
N1—C6—H6B	109.5	C4—N4—H4	126.5
H6A—C6—H6B	109.5	O5B—N5—O5A	40.7 (5)
N1—C6—H6C	109.5	O5B—N5—O4A	99.3 (7)
H6A—C6—H6C	109.5	O5A—N5—O4A	122.9 (2)
H6B—C6—H6C	109.5	O5B—N5—O4B	120.0 (6)
N2—C7—H7A	109.5	O5A—N5—O4B	100.8 (4)
N2—C7—H7B	109.5	O4A—N5—O4B	60.1 (4)
H7A—C7—H7B	109.5	O5B—N5—C10	123.0 (6)
N2—C7—H7C	109.5	O5A—N5—C10	117.5 (2)
H7A—C7—H7C	109.5	O4A—N5—C10	119.19 (17)
H7B—C7—H7C	109.5	O4B—N5—C10	115.5 (3)
N3—C8—H8A	109.5	O7—N6—O6	123.39 (17)
N3—C8—H8B	109.5	O7—N6—C12	118.17 (16)
H8A—C8—H8B	109.5	O6—N6—C12	118.44 (17)
N3—C8—H8C	109.5	O8B—N7—O9B	118.9 (14)
H8A—C8—H8C	109.5	O8B—N7—O8A	26.9 (17)
H8B—C8—H8C	109.5	O9B—N7—O8A	106.1 (8)
O3—C9—C14	124.40 (15)	O8B—N7—O9A	117.8 (14)
O3—C9—C10	124.06 (16)	O9B—N7—O9A	39.2 (9)
C14—C9—C10	111.49 (14)	O8A—N7—O9A	124.4 (3)
C11—C10—C9	123.91 (16)	O8B—N7—C14	116.0 (12)
C11—C10—N5	116.72 (15)	O9B—N7—C14	124.2 (7)
C9—C10—N5	119.33 (15)	O8A—N7—C14	118.6 (3)
C10—C11—C12	119.61 (16)	O9A—N7—C14	116.9 (2)
C10—C11—H11	120.2	N5—O4A—O4B	63.2 (3)
C12—C11—H11	120.2	O4A—O4B—N5	56.7 (4)
C11—C12—C13	121.20 (15)	O5B—O5A—N5	65.1 (7)
C11—C12—N6	119.73 (16)	O5A—O5B—N5	74.3 (7)
C13—C12—N6	119.07 (16)	O9B—O9A—N7	65.0 (10)
C14—C13—C12	118.36 (16)	O9A—O9B—N7	75.8 (12)

C4—C1—C2—O1	177.94 (17)	O2—C3—N3—C8	−3.4 (2)
N1—C1—C2—O1	0.7 (3)	N2—C3—N3—C8	177.33 (14)
C4—C1—C2—N2	−2.1 (2)	N1—C5—N4—C4	−0.12 (19)
N1—C1—C2—N2	−179.30 (16)	C1—C4—N4—C5	0.36 (17)
N1—C1—C4—N3	178.70 (14)	N3—C4—N4—C5	−178.74 (16)
C2—C1—C4—N3	0.9 (2)	C11—C10—N5—O5B	28.1 (8)
N1—C1—C4—N4	−0.47 (18)	C9—C10—N5—O5B	−153.8 (8)
C2—C1—C4—N4	−178.27 (14)	C11—C10—N5—O5A	−18.9 (3)
O3—C9—C10—C11	−177.61 (16)	C9—C10—N5—O5A	159.1 (3)
C14—C9—C10—C11	0.1 (2)	C11—C10—N5—O4A	153.8 (2)
O3—C9—C10—N5	4.5 (2)	C9—C10—N5—O4A	−28.2 (3)
C14—C9—C10—N5	−177.84 (15)	C11—C10—N5—O4B	−137.7 (5)
C9—C10—C11—C12	0.3 (2)	C9—C10—N5—O4B	40.4 (5)
N5—C10—C11—C12	178.27 (15)	C11—C12—N6—O7	172.46 (17)
C10—C11—C12—C13	0.2 (3)	C13—C12—N6—O7	−7.2 (3)
C10—C11—C12—N6	−179.48 (15)	C11—C12—N6—O6	−7.5 (3)
C11—C12—C13—C14	−1.0 (3)	C13—C12—N6—O6	172.82 (16)
N6—C12—C13—C14	178.64 (15)	C13—C14—N7—O8B	−11.0 (18)
C12—C13—C14—C9	1.5 (3)	C9—C14—N7—O8B	168.4 (18)
C12—C13—C14—N7	−179.15 (15)	C13—C14—N7—O9B	−180.0 (11)
O3—C9—C14—C13	176.68 (17)	C9—C14—N7—O9B	−0.5 (11)
C10—C9—C14—C13	−1.0 (2)	C13—C14—N7—O8A	−41.2 (3)
O3—C9—C14—N7	−2.7 (3)	C9—C14—N7—O8A	138.2 (3)
C10—C9—C14—N7	179.64 (15)	C13—C14—N7—O9A	134.9 (2)
N4—C5—N1—C1	−0.2 (2)	C9—C14—N7—O9A	−45.6 (3)
N4—C5—N1—C6	177.33 (17)	O5B—N5—O4A—O4B	−119.4 (6)
C4—C1—N1—C5	0.40 (19)	O5A—N5—O4A—O4B	−83.4 (4)
C2—C1—N1—C5	177.97 (17)	C10—N5—O4A—O4B	104.3 (4)
C4—C1—N1—C6	−177.08 (17)	O5B—N5—O4B—O4A	83.3 (8)
C2—C1—N1—C6	0.5 (3)	O5A—N5—O4B—O4A	121.9 (3)
O2—C3—N2—C2	176.27 (17)	C10—N5—O4B—O4A	−110.4 (3)
N3—C3—N2—C2	−4.5 (2)	O4A—N5—O5A—O5B	−62.8 (11)
O2—C3—N2—C7	−2.4 (2)	O4B—N5—O5A—O5B	−124.0 (11)
N3—C3—N2—C7	176.80 (15)	C10—N5—O5A—O5B	109.6 (10)
O1—C2—N2—C3	−176.02 (16)	O4A—N5—O5B—O5A	130.9 (9)
C1—C2—N2—C3	4.0 (2)	O4B—N5—O5B—O5A	70.1 (12)
O1—C2—N2—C7	2.7 (2)	C10—N5—O5B—O5A	−95.1 (9)
C1—C2—N2—C7	−177.30 (15)	O8B—N7—O9A—O9B	−103 (2)
C1—C4—N3—C3	−1.2 (2)	O8A—N7—O9A—O9B	−72.0 (14)
N4—C4—N3—C3	177.82 (15)	C14—N7—O9A—O9B	112.1 (13)
C1—C4—N3—C8	−175.52 (15)	O8B—N7—O9B—O9A	100 (2)
N4—C4—N3—C8	3.5 (2)	O8A—N7—O9B—O9A	125.3 (10)
O2—C3—N3—C4	−178.03 (16)	C14—N7—O9B—O9A	−91.7 (12)
N2—C3—N3—C4	2.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O3	0.86	1.83	2.671 (2)	167
C5—H5···O9A	0.93	2.36	2.915 (4)	118
C6—H6A···O2ⁱ	0.96	2.43	3.350 (2)	161
C7—H7A···O6ⁱⁱ	0.96	2.54	3.308 (2)	137
C8—H8A···O3	0.96	2.31	3.256 (2)	169

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

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