1,1′-Methyl­enebis(4-methyl-1H-triazolium) dipicrate

Jin, C.-M.; Chen, C.-Y.; Wang, W.-D.; Zhou, X.-W.

doi:10.1107/S1600536806045181

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1,1'-Methylenebis(4-methyl-1H-triazolium) dipicrate

C.-M. Jin, C.-Y. Chen, W.-D. Wang and X.-W. Zhou

In the crystal structure of the title compound, C₇H₁₂N₆²⁺·2C₆H₂N₃O₇^-, the asymmetric unit contains two picrate anions and one 1,1'-methylenebis(4-methyl-1H-triazolium) dication. The dihedral angle between the triazole rings of the dication is 76.1 (2)°,

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045181/xu2143sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045181/xu2143Isup2.hkl Contains datablock I

CCDC reference: 630512

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.002 Å
R factor = 0.046
wR factor = 0.133
Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  O2     ..  C5      ..       2.91 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O8     ..  C3      ..       2.91 Ang.

Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N10
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C3      ..       2.97 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O10    ..  C3      ..       2.99 Ang.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

1,1'-Methylenebis(4-methyl-1H-triazolium) dipicrate top

Crystal data top

C₇H₁₂N₆²⁺·2C₆H₂N₃O₇⁻	Z = 2
M_r = 636.44	F(000) = 652
Triclinic, P1	D_x = 1.666 Mg m⁻³
Hall symbol: -P 1	Melting point: 488K-490 K
a = 7.0658 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8036 (6) Å	Cell parameters from 6107 reflections
c = 20.5831 (14) Å	θ = 2.3–28.2°
α = 96.587 (1)°	µ = 0.15 mm⁻¹
β = 90.122 (1)°	T = 292 K
γ = 94.255 (1)°	Block, yellow
V = 1268.33 (15) Å³	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4435 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.046
Graphite monochromator	θ_max = 27.0°, θ_min = 2.0°
φ and ω scans	h = −9→9
14366 measured reflections	k = −11→11
5485 independent reflections	l = −26→26

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) = 0.133	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0674P)²] where P = (F_o² + 2F_c²)/3
5485 reflections	(Δ/σ)_max < 0.001
408 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.25 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
C1	0.8452 (3)	1.2680 (2)	0.26685 (11)	0.0598 (5)
H1A	0.9088	1.1780	0.2730	0.090*
H1B	0.8550	1.3380	0.3063	0.090*
H1C	0.9031	1.3164	0.2316	0.090*
C2	0.4944 (3)	1.29727 (19)	0.27592 (9)	0.0442 (4)
H2	0.5035	1.3831	0.3069	0.053*
C3	0.5777 (2)	1.10902 (18)	0.20943 (7)	0.0362 (3)
H3	0.6478	1.0378	0.1850	0.043*
C4	0.2568 (3)	1.0074 (2)	0.17085 (8)	0.0471 (4)
H4A	0.3190	0.9573	0.1332	0.057*
H4B	0.1563	1.0635	0.1551	0.057*
C5	0.2620 (2)	0.78501 (19)	0.23424 (8)	0.0422 (4)
H5	0.3891	0.7658	0.2289	0.051*
C6	−0.0308 (2)	0.7730 (2)	0.26073 (9)	0.0462 (4)
H6	−0.1448	0.7394	0.2787	0.055*
C7	0.1709 (3)	0.5850 (2)	0.30640 (11)	0.0575 (5)
H7A	0.1775	0.4911	0.2781	0.086*
H7B	0.0698	0.5734	0.3369	0.086*
H7C	0.2889	0.6093	0.3298	0.086*
C8	0.6822 (2)	0.7123 (2)	0.40862 (8)	0.0406 (4)
C9	0.6749 (2)	0.87732 (19)	0.41929 (7)	0.0381 (4)
C10	0.7250 (2)	0.9661 (2)	0.47706 (8)	0.0405 (4)
H10	0.7162	1.0716	0.4810	0.049*
C11	0.7881 (2)	0.8976 (2)	0.52895 (8)	0.0426 (4)
C12	0.7965 (3)	0.7394 (2)	0.52445 (8)	0.0462 (4)
H12	0.8352	0.6934	0.5602	0.055*
C13	0.7474 (3)	0.6530 (2)	0.46723 (9)	0.0444 (4)
C14	0.6671 (2)	0.73578 (18)	0.08687 (7)	0.0353 (3)
C15	0.6724 (2)	0.57001 (18)	0.07777 (8)	0.0368 (3)
C16	0.7299 (2)	0.48787 (19)	0.02140 (8)	0.0401 (4)
H16	0.7242	0.3813	0.0177	0.048*
C17	0.7961 (2)	0.5654 (2)	−0.02971 (8)	0.0418 (4)
C18	0.8088 (2)	0.7245 (2)	−0.02421 (8)	0.0440 (4)
H18	0.8562	0.7760	−0.0584	0.053*
C19	0.7513 (2)	0.80387 (19)	0.03166 (8)	0.0409 (4)
N1	0.64543 (19)	1.22482 (14)	0.25114 (6)	0.0373 (3)
N2	0.3361 (2)	1.23246 (17)	0.25121 (7)	0.0462 (4)
N3	0.39281 (19)	1.11307 (15)	0.20880 (6)	0.0375 (3)
N4	0.17587 (19)	0.89257 (16)	0.21023 (6)	0.0394 (3)
N5	−0.01164 (19)	0.88714 (18)	0.22611 (7)	0.0466 (4)
N6	0.13510 (19)	0.70840 (15)	0.26752 (7)	0.0404 (3)
N7	0.6101 (2)	0.96010 (19)	0.36757 (7)	0.0458 (4)
N8	0.8428 (2)	0.9904 (2)	0.58924 (7)	0.0541 (4)
N9	0.7642 (3)	0.4882 (2)	0.46542 (10)	0.0642 (5)
N10	0.6096 (2)	0.48227 (17)	0.13045 (7)	0.0463 (3)
N11	0.8541 (2)	0.4803 (2)	−0.08951 (8)	0.0540 (4)
N12	0.7765 (3)	0.97110 (18)	0.03608 (8)	0.0537 (4)
O1	0.6363 (2)	0.62960 (16)	0.35715 (6)	0.0589 (4)
O2	0.6002 (2)	0.89723 (19)	0.31130 (6)	0.0670 (4)
O3	0.5659 (3)	1.09097 (18)	0.38168 (7)	0.0714 (4)
O4	0.8252 (3)	1.12783 (18)	0.59354 (8)	0.0759 (5)
O5	0.9074 (3)	0.9288 (2)	0.63359 (7)	0.0824 (5)
O6	0.7262 (4)	0.4285 (2)	0.51424 (10)	0.1077 (7)
O7	0.8260 (4)	0.4190 (2)	0.41641 (10)	0.1041 (7)
O8	0.59240 (18)	0.80976 (14)	0.13349 (6)	0.0473 (3)
O9	0.6085 (3)	0.54589 (18)	0.18632 (7)	0.0860 (6)
O10	0.5619 (3)	0.34698 (16)	0.11732 (8)	0.0715 (4)
O11	0.8457 (2)	0.33982 (19)	−0.09285 (8)	0.0746 (5)
O12	0.9113 (3)	0.5514 (2)	−0.13432 (7)	0.0786 (5)
O13	0.7588 (3)	1.0309 (2)	−0.01386 (8)	0.0954 (6)
O14	0.8243 (2)	1.04396 (16)	0.08849 (7)	0.0684 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0457 (11)	0.0615 (12)	0.0689 (13)	−0.0073 (9)	−0.0054 (9)	−0.0001 (10)
C2	0.0531 (10)	0.0348 (8)	0.0446 (9)	0.0078 (7)	0.0047 (8)	0.0012 (7)
C3	0.0415 (9)	0.0341 (8)	0.0333 (8)	0.0031 (6)	0.0039 (6)	0.0056 (6)
C4	0.0452 (10)	0.0623 (11)	0.0326 (8)	−0.0042 (8)	−0.0041 (7)	0.0059 (8)
C5	0.0331 (8)	0.0433 (9)	0.0461 (9)	−0.0020 (7)	0.0010 (7)	−0.0090 (7)
C6	0.0342 (9)	0.0529 (10)	0.0490 (10)	−0.0025 (7)	0.0042 (7)	−0.0012 (8)
C7	0.0575 (12)	0.0351 (9)	0.0782 (14)	−0.0001 (8)	−0.0009 (10)	0.0022 (9)
C8	0.0376 (8)	0.0479 (9)	0.0343 (8)	−0.0018 (7)	0.0021 (6)	−0.0006 (7)
C9	0.0360 (8)	0.0478 (9)	0.0307 (8)	0.0028 (7)	0.0015 (6)	0.0055 (7)
C10	0.0400 (9)	0.0422 (9)	0.0384 (8)	0.0033 (7)	0.0033 (7)	0.0002 (7)
C11	0.0429 (9)	0.0503 (10)	0.0329 (8)	0.0033 (7)	−0.0029 (7)	−0.0028 (7)
C12	0.0494 (10)	0.0543 (10)	0.0361 (9)	0.0066 (8)	−0.0037 (7)	0.0084 (8)
C13	0.0469 (10)	0.0415 (9)	0.0447 (9)	0.0031 (7)	0.0025 (7)	0.0045 (7)
C14	0.0349 (8)	0.0403 (8)	0.0299 (7)	0.0000 (6)	−0.0008 (6)	0.0031 (6)
C15	0.0350 (8)	0.0410 (8)	0.0341 (8)	−0.0018 (6)	−0.0027 (6)	0.0066 (6)
C16	0.0358 (8)	0.0403 (9)	0.0426 (9)	0.0012 (7)	−0.0066 (7)	−0.0010 (7)
C17	0.0376 (8)	0.0535 (10)	0.0323 (8)	0.0056 (7)	−0.0027 (6)	−0.0046 (7)
C18	0.0463 (9)	0.0551 (10)	0.0318 (8)	0.0041 (8)	0.0035 (7)	0.0097 (7)
C19	0.0471 (9)	0.0409 (9)	0.0355 (8)	0.0033 (7)	0.0017 (7)	0.0072 (7)
N1	0.0401 (7)	0.0325 (7)	0.0395 (7)	0.0010 (5)	0.0011 (5)	0.0066 (5)
N2	0.0455 (8)	0.0455 (8)	0.0482 (8)	0.0114 (6)	0.0056 (6)	0.0029 (7)
N3	0.0402 (7)	0.0379 (7)	0.0346 (7)	0.0026 (5)	0.0014 (5)	0.0056 (5)
N4	0.0330 (7)	0.0470 (8)	0.0349 (7)	−0.0037 (6)	−0.0011 (5)	−0.0049 (6)
N5	0.0328 (7)	0.0586 (9)	0.0468 (8)	0.0009 (6)	−0.0009 (6)	0.0005 (7)
N6	0.0378 (7)	0.0355 (7)	0.0444 (8)	−0.0018 (5)	0.0007 (6)	−0.0082 (6)
N7	0.0407 (8)	0.0600 (10)	0.0385 (8)	0.0074 (7)	0.0020 (6)	0.0115 (7)
N8	0.0576 (10)	0.0636 (11)	0.0380 (8)	0.0016 (8)	−0.0055 (7)	−0.0051 (7)
N9	0.0817 (13)	0.0471 (9)	0.0633 (11)	0.0043 (9)	−0.0068 (9)	0.0052 (9)
N10	0.0545 (9)	0.0422 (8)	0.0428 (8)	−0.0005 (6)	−0.0011 (6)	0.0102 (6)
N11	0.0478 (9)	0.0717 (11)	0.0386 (8)	0.0061 (8)	−0.0032 (7)	−0.0115 (8)
N12	0.0723 (11)	0.0461 (9)	0.0447 (9)	0.0045 (7)	0.0156 (7)	0.0131 (7)
O1	0.0723 (9)	0.0583 (8)	0.0409 (7)	−0.0062 (7)	−0.0065 (6)	−0.0088 (6)
O2	0.0811 (10)	0.0863 (11)	0.0352 (7)	0.0189 (8)	−0.0111 (6)	0.0062 (7)
O3	0.0985 (12)	0.0632 (9)	0.0583 (9)	0.0248 (8)	0.0029 (8)	0.0201 (7)
O4	0.1048 (13)	0.0599 (10)	0.0573 (9)	0.0076 (8)	−0.0127 (8)	−0.0187 (7)
O5	0.1096 (14)	0.0921 (12)	0.0439 (8)	0.0101 (10)	−0.0308 (8)	−0.0006 (8)
O6	0.172 (2)	0.0641 (11)	0.0935 (14)	0.0086 (12)	0.0002 (14)	0.0358 (10)
O7	0.159 (2)	0.0624 (11)	0.0896 (13)	0.0338 (12)	0.0026 (13)	−0.0125 (10)
O8	0.0546 (7)	0.0450 (7)	0.0408 (6)	−0.0001 (5)	0.0129 (5)	0.0002 (5)
O9	0.1537 (18)	0.0614 (9)	0.0426 (8)	−0.0042 (10)	0.0209 (9)	0.0121 (7)
O10	0.1033 (12)	0.0458 (8)	0.0652 (9)	−0.0108 (8)	−0.0032 (8)	0.0166 (7)
O11	0.0857 (11)	0.0662 (10)	0.0628 (9)	0.0014 (8)	0.0034 (8)	−0.0291 (8)
O12	0.0953 (12)	0.1017 (13)	0.0382 (8)	0.0165 (10)	0.0175 (8)	−0.0005 (8)
O13	0.170 (2)	0.0637 (10)	0.0590 (10)	0.0134 (11)	0.0092 (11)	0.0307 (8)
O14	0.0978 (12)	0.0479 (8)	0.0557 (9)	−0.0103 (7)	0.0160 (8)	−0.0005 (7)

Geometric parameters (Å, º) top

C1—N1	1.460 (2)	C11—C12	1.391 (3)
C1—H1A	0.9600	C11—N8	1.441 (2)
C1—H1B	0.9600	C12—C13	1.356 (2)
C1—H1C	0.9600	C12—H12	0.9300
C2—N2	1.293 (2)	C13—N9	1.460 (2)
C2—N1	1.354 (2)	C14—O8	1.2384 (19)
C2—H2	0.9300	C14—C15	1.453 (2)
C3—N3	1.310 (2)	C14—C19	1.453 (2)
C3—N1	1.315 (2)	C15—C16	1.374 (2)
C3—H3	0.9300	C15—N10	1.454 (2)
C4—N3	1.448 (2)	C16—C17	1.383 (2)
C4—N4	1.452 (2)	C16—H16	0.9300
C4—H4A	0.9700	C17—C18	1.388 (3)
C4—H4B	0.9700	C17—N11	1.443 (2)
C5—N4	1.305 (2)	C18—C19	1.355 (2)
C5—N6	1.322 (2)	C18—H18	0.9300
C5—H5	0.9300	C19—N12	1.462 (2)
C6—N5	1.296 (2)	N2—N3	1.3714 (19)
C6—N6	1.354 (2)	N4—N5	1.3640 (19)
C6—H6	0.9300	N7—O3	1.219 (2)
C7—N6	1.457 (3)	N7—O2	1.2245 (19)
C7—H7A	0.9600	N8—O5	1.219 (2)
C7—H7B	0.9600	N8—O4	1.219 (2)
C7—H7C	0.9600	N9—O6	1.208 (3)
C8—O1	1.243 (2)	N9—O7	1.216 (3)
C8—C9	1.449 (2)	N10—O10	1.2130 (19)
C8—C13	1.456 (2)	N10—O9	1.220 (2)
C9—C10	1.376 (2)	N11—O12	1.226 (2)
C9—N7	1.449 (2)	N11—O11	1.227 (2)
C10—C11	1.375 (2)	N12—O13	1.218 (2)
C10—H10	0.9300	N12—O14	1.223 (2)

N1—C1—H1A	109.5	O8—C14—C19	123.88 (15)
N1—C1—H1B	109.5	C15—C14—C19	110.92 (14)
H1A—C1—H1B	109.5	C16—C15—C14	124.28 (15)
N1—C1—H1C	109.5	C16—C15—N10	116.64 (15)
H1A—C1—H1C	109.5	C14—C15—N10	119.07 (14)
H1B—C1—H1C	109.5	C15—C16—C17	119.22 (15)
N2—C2—N1	111.74 (15)	C15—C16—H16	120.4
N2—C2—H2	124.1	C17—C16—H16	120.4
N1—C2—H2	124.1	C16—C17—C18	120.92 (15)
N3—C3—N1	106.93 (14)	C16—C17—N11	119.68 (16)
N3—C3—H3	126.5	C18—C17—N11	119.39 (16)
N1—C3—H3	126.5	C19—C18—C17	119.14 (16)
N3—C4—N4	110.65 (13)	C19—C18—H18	120.4
N3—C4—H4A	109.5	C17—C18—H18	120.4
N4—C4—H4A	109.5	C18—C19—C14	125.15 (16)
N3—C4—H4B	109.5	C18—C19—N12	116.83 (15)
N4—C4—H4B	109.5	C14—C19—N12	118.03 (14)
H4A—C4—H4B	108.1	C3—N1—C2	106.80 (14)
N4—C5—N6	107.24 (15)	C3—N1—C1	126.48 (15)
N4—C5—H5	126.4	C2—N1—C1	126.71 (15)
N6—C5—H5	126.4	C2—N2—N3	103.20 (13)
N5—C6—N6	111.91 (15)	C3—N3—N2	111.32 (13)
N5—C6—H6	124.0	C3—N3—C4	127.12 (14)
N6—C6—H6	124.0	N2—N3—C4	121.54 (14)
N6—C7—H7A	109.5	C5—N4—N5	111.47 (14)
N6—C7—H7B	109.5	C5—N4—C4	127.72 (15)
H7A—C7—H7B	109.5	N5—N4—C4	120.80 (14)
N6—C7—H7C	109.5	C6—N5—N4	103.23 (14)
H7A—C7—H7C	109.5	C5—N6—C6	106.13 (15)
H7B—C7—H7C	109.5	C5—N6—C7	126.39 (15)
O1—C8—C9	125.55 (16)	C6—N6—C7	127.40 (16)
O1—C8—C13	123.38 (17)	O3—N7—O2	121.87 (16)
C9—C8—C13	111.06 (14)	O3—N7—C9	118.60 (15)
C10—C9—N7	115.31 (15)	O2—N7—C9	119.53 (15)
C10—C9—C8	124.37 (15)	O5—N8—O4	122.56 (16)
N7—C9—C8	120.32 (14)	O5—N8—C11	118.73 (17)
C11—C10—C9	119.46 (16)	O4—N8—C11	118.70 (16)
C11—C10—H10	120.3	O6—N9—O7	122.9 (2)
C9—C10—H10	120.3	O6—N9—C13	118.20 (19)
C10—C11—C12	120.87 (15)	O7—N9—C13	118.76 (19)
C10—C11—N8	119.62 (16)	O10—N10—O9	122.11 (16)
C12—C11—N8	119.50 (16)	O10—N10—C15	118.55 (15)
C13—C12—C11	119.18 (16)	O9—N10—C15	119.33 (15)
C13—C12—H12	120.4	O12—N11—O11	123.08 (17)
C11—C12—H12	120.4	O12—N11—C17	118.55 (17)
C12—C13—C8	125.04 (16)	O11—N11—C17	118.36 (17)
C12—C13—N9	116.28 (16)	O13—N12—O14	122.90 (18)
C8—C13—N9	118.69 (16)	O13—N12—C19	117.96 (17)
O8—C14—C15	125.10 (14)	O14—N12—C19	119.02 (15)

O1—C8—C9—C10	179.37 (17)	C2—N2—N3—C3	0.33 (18)
C13—C8—C9—C10	0.6 (2)	C2—N2—N3—C4	179.03 (14)
O1—C8—C9—N7	0.0 (3)	N4—C4—N3—C3	97.96 (19)
C13—C8—C9—N7	−178.79 (14)	N4—C4—N3—N2	−80.52 (19)
N7—C9—C10—C11	179.95 (15)	N6—C5—N4—N5	−1.28 (18)
C8—C9—C10—C11	0.5 (3)	N6—C5—N4—C4	179.15 (14)
C9—C10—C11—C12	−2.0 (3)	N3—C4—N4—C5	−66.7 (2)
C9—C10—C11—N8	179.25 (15)	N3—C4—N4—N5	113.77 (16)
C10—C11—C12—C13	2.2 (3)	N6—C6—N5—N4	0.49 (18)
N8—C11—C12—C13	−179.04 (17)	C5—N4—N5—C6	0.49 (18)
C11—C12—C13—C8	−1.0 (3)	C4—N4—N5—C6	−179.91 (15)
C11—C12—C13—N9	178.47 (17)	N4—C5—N6—C6	1.50 (18)
O1—C8—C13—C12	−179.17 (18)	N4—C5—N6—C7	−175.49 (15)
C9—C8—C13—C12	−0.4 (2)	N5—C6—N6—C5	−1.3 (2)
O1—C8—C13—N9	1.4 (3)	N5—C6—N6—C7	175.68 (16)
C9—C8—C13—N9	−179.81 (16)	C10—C9—N7—O3	−15.3 (2)
O8—C14—C15—C16	169.70 (16)	C8—C9—N7—O3	164.12 (17)
C19—C14—C15—C16	−6.7 (2)	C10—C9—N7—O2	165.02 (16)
O8—C14—C15—N10	−8.8 (2)	C8—C9—N7—O2	−15.5 (2)
C19—C14—C15—N10	174.74 (14)	C10—C11—N8—O5	−176.32 (18)
C14—C15—C16—C17	3.2 (2)	C12—C11—N8—O5	4.9 (3)
N10—C15—C16—C17	−178.22 (14)	C10—C11—N8—O4	2.6 (3)
C15—C16—C17—C18	1.3 (2)	C12—C11—N8—O4	−176.21 (18)
C15—C16—C17—N11	−179.08 (14)	C12—C13—N9—O6	36.2 (3)
C16—C17—C18—C19	−1.5 (3)	C8—C13—N9—O6	−144.3 (2)
N11—C17—C18—C19	178.95 (15)	C12—C13—N9—O7	−139.6 (2)
C17—C18—C19—C14	−3.0 (3)	C8—C13—N9—O7	39.9 (3)
C17—C18—C19—N12	177.07 (16)	C16—C15—N10—O10	−19.7 (2)
O8—C14—C19—C18	−169.82 (17)	C14—C15—N10—O10	158.91 (16)
C15—C14—C19—C18	6.7 (2)	C16—C15—N10—O9	159.39 (18)
O8—C14—C19—N12	10.1 (2)	C14—C15—N10—O9	−22.0 (2)
C15—C14—C19—N12	−173.40 (14)	C16—C17—N11—O12	179.57 (16)
N3—C3—N1—C2	0.62 (17)	C18—C17—N11—O12	−0.8 (2)
N3—C3—N1—C1	−178.54 (16)	C16—C17—N11—O11	−1.2 (2)
N2—C2—N1—C3	−0.44 (19)	C18—C17—N11—O11	178.43 (17)
N2—C2—N1—C1	178.72 (17)	C18—C19—N12—O13	34.1 (3)
N1—C2—N2—N3	0.07 (18)	C14—C19—N12—O13	−145.9 (2)
N1—C3—N3—N2	−0.61 (18)	C18—C19—N12—O14	−142.01 (18)
N1—C3—N3—C4	−179.22 (14)	C14—C19—N12—O14	38.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O7ⁱ	0.96	2.31	3.217 (3)	157
C2—H2···O1ⁱ	0.93	2.42	3.286 (2)	156
C3—H3···O8	0.93	2.17	2.914 (2)	136
C3—H3···O14	0.93	2.35	3.066 (2)	133
C4—H4A···O8	0.97	2.41	3.091 (2)	127
C4—H4A···O13ⁱⁱ	0.97	2.53	3.211 (2)	127
C5—H5···O2	0.93	2.39	2.911 (2)	115
C5—H5···O8	0.93	2.48	3.138 (2)	127
C6—H6···O1ⁱⁱⁱ	0.93	2.47	3.350 (2)	159
C6—H6···O2ⁱⁱⁱ	0.93	2.41	3.042 (2)	125
C7—H7A···N2^iv	0.96	2.62	3.467 (2)	148
C7—H7C···O1	0.96	2.51	3.429 (3)	161

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

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