1,1'-Methyl­enebis­(3-methyl­imidazolium) dipicrate

In the title compound, C₉H₁₂N₄²⁺·2C₆H₂N₃O₇^-, the asymmetric unit contains two picrate anions and one 1,1'-methyl­ene-bis­(3-methyl­imidazolium) dication. The dihedral angle between the two imidazole rings in the dication is 74.1 (2)°, and the benzene rings of the two picrate anions are almost perpendicular, making a dihedral angle of 98.9 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.050
• wR factor = 0.144
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O9     -   N8      ..       7.00 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.08
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3     ..  C6      ..       2.95 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O7     ..  C19     ..       2.99 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O12    ..  C2      ..       2.99 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O12    ..  C5      ..       3.00 Ang.

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

   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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, 2001); software used to prepare material for publication: SHELXTL.

1,1'-Methylene-bis(3-methylimidazolium) Dipicrate

Crystal data

C9H14N4^2+·2C6H2N3O7^−	F(000) = 652
Mr = 634.45	Dx = 1.627 Mg m^−3
Triclinic, P1	Melting point: 457-459K K
a = 7.8353 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.8777 (12) Å	Cell parameters from 5212 reflections
c = 13.2129 (12) Å	θ = 2.7–27.9°
α = 83.522 (2)°	µ = 0.14 mm^−1
β = 79.288 (2)°	T = 292 K
γ = 83.049 (2)°	Plate, yellow
V = 1294.7 (2) Å^3	0.30 × 0.20 × 0.20 mm
Z = 2

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5542 independent reflections
Radiation source: fine-focus sealed tube	4475 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
φ and ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.959, Tmax = 0.973	k = −16→16
11622 measured reflections	l = −16→16

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0784P)^2] where P = (Fo^2 + 2Fc^2)/3
5542 reflections	(Δ/σ)max < 0.001
408 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4280 (3)	0.56953 (17)	0.34102 (19)	0.0604 (6)
H1A	0.4630	0.5798	0.2673	0.091*
H1B	0.4288	0.4957	0.3622	0.091*
H1C	0.5079	0.5989	0.3741	0.091*
C2	0.1610 (2)	0.68050 (13)	0.30759 (13)	0.0381 (4)
H2	0.1962	0.6939	0.2366	0.046*
C3	0.1564 (3)	0.61879 (16)	0.46811 (14)	0.0520 (5)
H3	0.1896	0.5815	0.5270	0.062*
C4	0.0062 (3)	0.67934 (16)	0.46371 (14)	0.0496 (5)
H4	−0.0837	0.6928	0.5188	0.060*
C5	−0.1245 (2)	0.78944 (13)	0.32076 (13)	0.0371 (4)
H5A	−0.2274	0.7976	0.3739	0.045*
H5B	−0.1569	0.7602	0.2634	0.045*
C6	−0.0818 (2)	0.97273 (12)	0.34332 (12)	0.0337 (4)
H6	−0.1437	0.9748	0.4105	0.040*
C7	0.0393 (2)	0.91852 (14)	0.19130 (13)	0.0417 (4)
H7	0.0735	0.8766	0.1366	0.050*
C8	0.0791 (2)	1.01666 (14)	0.19365 (13)	0.0432 (4)
H8	0.1466	1.0555	0.1408	0.052*
C9	0.0120 (3)	1.15191 (14)	0.32365 (16)	0.0491 (5)
H9A	−0.0650	1.2040	0.2921	0.074*
H9B	0.1296	1.1703	0.3043	0.074*
H9C	−0.0217	1.1487	0.3975	0.074*
C10	0.5197 (2)	0.17527 (12)	0.33092 (12)	0.0323 (3)
C11	0.4279 (2)	0.09120 (12)	0.39194 (12)	0.0314 (3)
C12	0.4457 (2)	−0.00055 (12)	0.33445 (12)	0.0316 (3)
C13	0.5362 (2)	−0.00722 (13)	0.23556 (12)	0.0333 (3)
H13	0.5432	−0.0685	0.2032	0.040*
C14	0.6167 (2)	0.07851 (13)	0.18472 (11)	0.0340 (4)
C15	0.6093 (2)	0.16947 (13)	0.23220 (12)	0.0338 (4)
H15	0.6648	0.2264	0.1973	0.041*
C16	0.9975 (3)	0.41189 (14)	0.16040 (12)	0.0428 (4)
C17	0.8465 (3)	0.42732 (13)	0.11843 (13)	0.0411 (4)
H17	0.7463	0.4640	0.1522	0.049*
C18	0.8464 (2)	0.38804 (13)	0.02692 (12)	0.0354 (4)
C19	0.9958 (2)	0.33095 (12)	−0.03282 (11)	0.0322 (3)
C20	1.1446 (2)	0.31674 (13)	0.01973 (13)	0.0375 (4)
C21	1.1459 (3)	0.35423 (14)	0.11239 (13)	0.0426 (4)
H21	1.2451	0.3412	0.1429	0.051*
N1	0.2520 (2)	0.62150 (11)	0.37065 (11)	0.0407 (4)
N2	0.01021 (19)	0.71796 (10)	0.36190 (10)	0.0342 (3)
N3	−0.06198 (18)	0.89180 (11)	0.28572 (10)	0.0335 (3)
N4	0.00159 (18)	1.04913 (11)	0.28854 (10)	0.0363 (3)
N5	0.5219 (2)	0.27286 (11)	0.37738 (11)	0.0394 (3)
N6	0.36581 (19)	−0.09390 (11)	0.38308 (11)	0.0383 (3)
N7	0.7134 (2)	0.07209 (12)	0.08054 (11)	0.0443 (4)
N8	0.9988 (3)	0.45321 (15)	0.25746 (12)	0.0594 (5)
N9	0.6809 (2)	0.39846 (12)	−0.00983 (13)	0.0453 (4)
N10	1.3022 (2)	0.25519 (13)	−0.02623 (14)	0.0508 (4)
O1	0.4044 (2)	0.30040 (11)	0.44474 (13)	0.0689 (5)
O2	0.64564 (19)	0.32434 (11)	0.34494 (12)	0.0586 (4)
O3	0.34965 (17)	0.09640 (10)	0.48228 (9)	0.0443 (3)
O4	0.23557 (19)	−0.08531 (12)	0.44989 (11)	0.0593 (4)
O5	0.4319 (2)	−0.17914 (11)	0.35445 (12)	0.0647 (4)
O6	0.7149 (3)	−0.00787 (13)	0.03917 (11)	0.0740 (5)
O7	0.7924 (2)	0.14603 (12)	0.04028 (11)	0.0646 (5)
O8	1.1238 (3)	0.42306 (16)	0.30142 (12)	0.0825 (6)
O9	0.8751 (3)	0.51452 (13)	0.29274 (11)	0.0739 (5)
O10	0.54842 (19)	0.39254 (13)	0.05546 (14)	0.0701 (5)
O11	0.6803 (2)	0.41355 (14)	−0.10292 (12)	0.0687 (5)
O12	0.99250 (16)	0.29365 (10)	−0.11454 (9)	0.0412 (3)
O13	1.3482 (2)	0.26404 (15)	−0.11942 (13)	0.0746 (5)
O14	1.3812 (2)	0.19618 (13)	0.03302 (15)	0.0781 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0554 (13)	0.0509 (12)	0.0738 (14)	0.0107 (10)	−0.0199 (11)	−0.0039 (10)
C2	0.0463 (10)	0.0348 (8)	0.0310 (8)	−0.0015 (7)	−0.0031 (7)	−0.0026 (6)
C3	0.0718 (14)	0.0515 (11)	0.0348 (9)	−0.0127 (10)	−0.0165 (9)	0.0065 (8)
C4	0.0636 (13)	0.0544 (11)	0.0280 (8)	−0.0126 (10)	0.0009 (8)	0.0002 (8)
C5	0.0356 (9)	0.0389 (9)	0.0354 (8)	−0.0052 (7)	0.0006 (7)	−0.0073 (7)
C6	0.0353 (9)	0.0356 (8)	0.0270 (7)	0.0000 (7)	−0.0005 (6)	−0.0016 (6)
C7	0.0467 (10)	0.0462 (10)	0.0268 (8)	−0.0011 (8)	0.0048 (7)	−0.0031 (7)
C8	0.0457 (10)	0.0464 (10)	0.0313 (8)	−0.0035 (8)	0.0048 (8)	0.0028 (7)
C9	0.0552 (12)	0.0358 (9)	0.0554 (11)	−0.0092 (8)	−0.0039 (9)	−0.0047 (8)
C10	0.0332 (8)	0.0314 (8)	0.0314 (8)	−0.0031 (6)	−0.0033 (7)	−0.0030 (6)
C11	0.0294 (8)	0.0353 (8)	0.0271 (7)	−0.0038 (6)	−0.0004 (6)	0.0003 (6)
C12	0.0302 (8)	0.0348 (8)	0.0293 (7)	−0.0078 (6)	−0.0032 (6)	0.0004 (6)
C13	0.0366 (9)	0.0346 (8)	0.0290 (7)	−0.0052 (7)	−0.0051 (7)	−0.0039 (6)
C14	0.0352 (9)	0.0404 (9)	0.0239 (7)	−0.0040 (7)	0.0001 (6)	−0.0008 (6)
C15	0.0327 (8)	0.0343 (8)	0.0321 (8)	−0.0068 (6)	−0.0021 (7)	0.0046 (6)
C16	0.0649 (12)	0.0407 (9)	0.0254 (8)	−0.0260 (9)	−0.0026 (8)	−0.0008 (7)
C17	0.0520 (11)	0.0366 (9)	0.0322 (8)	−0.0155 (8)	0.0071 (8)	−0.0053 (7)
C18	0.0393 (9)	0.0328 (8)	0.0333 (8)	−0.0096 (7)	−0.0016 (7)	−0.0015 (6)
C19	0.0404 (9)	0.0291 (8)	0.0260 (7)	−0.0087 (6)	−0.0016 (7)	0.0005 (6)
C20	0.0417 (10)	0.0355 (9)	0.0358 (8)	−0.0093 (7)	−0.0062 (7)	−0.0004 (7)
C21	0.0556 (11)	0.0427 (10)	0.0341 (8)	−0.0210 (8)	−0.0156 (8)	0.0066 (7)
N1	0.0507 (9)	0.0319 (7)	0.0414 (8)	−0.0055 (6)	−0.0141 (7)	−0.0010 (6)
N2	0.0434 (8)	0.0321 (7)	0.0271 (6)	−0.0083 (6)	−0.0025 (6)	−0.0041 (5)
N3	0.0358 (7)	0.0365 (7)	0.0258 (6)	−0.0011 (6)	−0.0004 (5)	−0.0038 (5)
N4	0.0389 (8)	0.0350 (7)	0.0326 (7)	−0.0019 (6)	−0.0033 (6)	0.0005 (5)
N5	0.0460 (8)	0.0325 (7)	0.0366 (7)	−0.0041 (6)	−0.0003 (6)	−0.0018 (6)
N6	0.0433 (8)	0.0387 (8)	0.0330 (7)	−0.0130 (6)	−0.0023 (6)	−0.0016 (6)
N7	0.0513 (9)	0.0487 (9)	0.0291 (7)	−0.0088 (7)	0.0045 (7)	−0.0030 (6)
N8	0.0965 (15)	0.0585 (11)	0.0287 (8)	−0.0427 (11)	−0.0046 (9)	−0.0009 (7)
N9	0.0391 (9)	0.0421 (8)	0.0542 (9)	−0.0017 (6)	−0.0033 (7)	−0.0132 (7)
N10	0.0454 (9)	0.0508 (10)	0.0601 (11)	−0.0031 (7)	−0.0168 (8)	−0.0117 (8)
O1	0.0792 (11)	0.0466 (8)	0.0698 (10)	−0.0111 (7)	0.0290 (9)	−0.0221 (7)
O2	0.0581 (9)	0.0446 (8)	0.0730 (10)	−0.0197 (7)	0.0047 (7)	−0.0161 (7)
O3	0.0521 (8)	0.0473 (7)	0.0295 (6)	−0.0117 (6)	0.0094 (5)	−0.0068 (5)
O4	0.0570 (9)	0.0568 (8)	0.0573 (8)	−0.0246 (7)	0.0188 (7)	−0.0043 (7)
O5	0.0842 (11)	0.0366 (7)	0.0683 (10)	−0.0197 (7)	0.0106 (8)	−0.0092 (6)
O6	0.1080 (14)	0.0677 (10)	0.0416 (8)	−0.0290 (9)	0.0232 (8)	−0.0236 (7)
O7	0.0826 (11)	0.0588 (9)	0.0413 (7)	−0.0226 (8)	0.0256 (7)	−0.0015 (6)
O8	0.1143 (15)	0.1054 (14)	0.0417 (8)	−0.0420 (12)	−0.0295 (10)	−0.0066 (8)
O9	0.1170 (15)	0.0643 (10)	0.0400 (8)	−0.0303 (10)	0.0103 (9)	−0.0207 (7)
O10	0.0407 (8)	0.0745 (11)	0.0869 (12)	−0.0061 (7)	0.0062 (8)	−0.0018 (9)
O11	0.0591 (9)	0.0954 (12)	0.0559 (9)	0.0178 (8)	−0.0236 (8)	−0.0306 (8)
O12	0.0458 (7)	0.0493 (7)	0.0303 (6)	−0.0062 (5)	−0.0055 (5)	−0.0117 (5)
O13	0.0505 (9)	0.1017 (14)	0.0651 (10)	0.0076 (9)	0.0034 (8)	−0.0188 (9)
O14	0.0788 (12)	0.0613 (10)	0.1052 (14)	0.0167 (9)	−0.0539 (11)	−0.0171 (9)

Geometric parameters (Å, º)

C1—N1	1.462 (3)	C11—C12	1.455 (2)
C1—H1A	0.9600	C12—C13	1.372 (2)
C1—H1B	0.9600	C12—N6	1.452 (2)
C1—H1C	0.9600	C13—C14	1.383 (2)
C2—N1	1.314 (2)	C13—H13	0.9300
C2—N2	1.330 (2)	C14—C15	1.380 (2)
C2—H2	0.9300	C14—N7	1.4484 (19)
C3—C4	1.338 (3)	C15—H15	0.9300
C3—N1	1.363 (2)	C16—C17	1.382 (3)
C3—H3	0.9300	C16—C21	1.389 (3)
C4—N2	1.377 (2)	C16—N8	1.445 (2)
C4—H4	0.9300	C17—C18	1.362 (2)
C5—N2	1.457 (2)	C17—H17	0.9300
C5—N3	1.458 (2)	C18—N9	1.453 (2)
C5—H5A	0.9700	C18—C19	1.454 (2)
C5—H5B	0.9700	C19—O12	1.2361 (19)
C6—N4	1.318 (2)	C19—C20	1.448 (2)
C6—N3	1.336 (2)	C20—C21	1.368 (2)
C6—H6	0.9300	C20—N10	1.454 (2)
C7—C8	1.343 (3)	C21—H21	0.9300
C7—N3	1.381 (2)	N5—O1	1.2058 (19)
C7—H7	0.9300	N5—O2	1.2247 (19)
C8—N4	1.375 (2)	N6—O4	1.2218 (19)
C8—H8	0.9300	N6—O5	1.2246 (19)
C9—N4	1.467 (2)	N7—O7	1.216 (2)
C9—H9A	0.9600	N7—O6	1.217 (2)
C9—H9B	0.9600	N8—O9	1.229 (3)
C9—H9C	0.9600	N8—O8	1.231 (3)
C10—C15	1.367 (2)	N9—O11	1.224 (2)
C10—C11	1.454 (2)	N9—O10	1.224 (2)
C10—N5	1.463 (2)	N10—O13	1.213 (2)
C11—O3	1.2415 (18)	N10—O14	1.227 (2)
N1—C1—H1A	109.5	C10—C15—C14	119.48 (15)
N1—C1—H1B	109.5	C10—C15—H15	120.3
H1A—C1—H1B	109.5	C14—C15—H15	120.3
N1—C1—H1C	109.5	C17—C16—C21	120.90 (16)
H1A—C1—H1C	109.5	C17—C16—N8	119.42 (19)
H1B—C1—H1C	109.5	C21—C16—N8	119.6 (2)
N1—C2—N2	108.87 (15)	C18—C17—C16	119.03 (17)
N1—C2—H2	125.6	C18—C17—H17	120.5
N2—C2—H2	125.6	C16—C17—H17	120.5
C4—C3—N1	107.68 (16)	C17—C18—N9	117.04 (16)
C4—C3—H3	126.2	C17—C18—C19	125.01 (17)
N1—C3—H3	126.2	N9—C18—C19	117.83 (14)
C3—C4—N2	106.85 (16)	O12—C19—C20	124.45 (15)
C3—C4—H4	126.6	O12—C19—C18	124.21 (16)
N2—C4—H4	126.6	C20—C19—C18	111.19 (14)
N2—C5—N3	110.58 (14)	C21—C20—C19	124.45 (17)
N2—C5—H5A	109.5	C21—C20—N10	117.09 (17)
N3—C5—H5A	109.5	C19—C20—N10	118.41 (15)
N2—C5—H5B	109.5	C20—C21—C16	119.32 (18)
N3—C5—H5B	109.5	C20—C21—H21	120.3
H5A—C5—H5B	108.1	C16—C21—H21	120.3
N4—C6—N3	108.19 (13)	C2—N1—C3	108.61 (16)
N4—C6—H6	125.9	C2—N1—C1	125.42 (16)
N3—C6—H6	125.9	C3—N1—C1	125.95 (17)
C8—C7—N3	106.73 (15)	C2—N2—C4	107.98 (16)
C8—C7—H7	126.6	C2—N2—C5	125.73 (14)
N3—C7—H7	126.6	C4—N2—C5	126.28 (15)
C7—C8—N4	107.35 (15)	C6—N3—C7	108.62 (14)
C7—C8—H8	126.3	C6—N3—C5	125.23 (13)
N4—C8—H8	126.3	C7—N3—C5	125.94 (14)
N4—C9—H9A	109.5	C6—N4—C8	109.11 (14)
N4—C9—H9B	109.5	C6—N4—C9	125.50 (14)
H9A—C9—H9B	109.5	C8—N4—C9	125.39 (15)
N4—C9—H9C	109.5	O1—N5—O2	122.27 (16)
H9A—C9—H9C	109.5	O1—N5—C10	120.13 (15)
H9B—C9—H9C	109.5	O2—N5—C10	117.60 (14)
C15—C10—C11	124.60 (15)	O4—N6—O5	122.27 (15)
C15—C10—N5	116.43 (14)	O4—N6—C12	119.61 (14)
C11—C10—N5	118.95 (13)	O5—N6—C12	118.11 (14)
O3—C11—C10	124.18 (15)	O7—N7—O6	123.61 (15)
O3—C11—C12	124.76 (14)	O7—N7—C14	118.01 (15)
C10—C11—C12	111.03 (13)	O6—N7—C14	118.35 (15)
C13—C12—N6	115.86 (14)	O9—N8—O8	123.45 (19)
C13—C12—C11	124.73 (14)	O9—N8—C16	118.9 (2)
N6—C12—C11	119.40 (13)	O8—N8—C16	117.6 (2)
C12—C13—C14	119.02 (15)	O11—N9—O10	123.60 (18)
C12—C13—H13	120.5	O11—N9—C18	119.14 (16)
C14—C13—H13	120.5	O10—N9—C18	117.26 (17)
C15—C14—C13	121.14 (14)	O13—N10—O14	123.68 (19)
C15—C14—N7	119.39 (14)	O13—N10—C20	119.32 (16)
C13—C14—N7	119.46 (15)	O14—N10—C20	117.00 (18)
N1—C3—C4—N2	0.8 (2)	N1—C2—N2—C5	177.82 (15)
N3—C7—C8—N4	−0.3 (2)	C3—C4—N2—C2	−0.1 (2)
C15—C10—C11—O3	178.57 (16)	C3—C4—N2—C5	−178.63 (16)
N5—C10—C11—O3	0.1 (2)	N3—C5—N2—C2	−66.6 (2)
C15—C10—C11—C12	0.7 (2)	N3—C5—N2—C4	111.68 (18)
N5—C10—C11—C12	−177.82 (14)	N4—C6—N3—C7	0.55 (19)
O3—C11—C12—C13	−178.17 (16)	N4—C6—N3—C5	175.62 (15)
C10—C11—C12—C13	−0.3 (2)	C8—C7—N3—C6	−0.1 (2)
O3—C11—C12—N6	0.9 (3)	C8—C7—N3—C5	−175.16 (16)
C10—C11—C12—N6	178.79 (14)	N2—C5—N3—C6	−91.76 (18)
N6—C12—C13—C14	−179.54 (15)	N2—C5—N3—C7	82.5 (2)
C11—C12—C13—C14	−0.4 (3)	N3—C6—N4—C8	−0.75 (19)
C12—C13—C14—C15	0.8 (3)	N3—C6—N4—C9	180.00 (16)
C12—C13—C14—N7	179.67 (16)	C7—C8—N4—C6	0.7 (2)
C11—C10—C15—C14	−0.3 (3)	C7—C8—N4—C9	179.92 (17)
N5—C10—C15—C14	178.20 (14)	C15—C10—N5—O1	154.02 (17)
C13—C14—C15—C10	−0.5 (3)	C11—C10—N5—O1	−27.4 (2)
N7—C14—C15—C10	−179.30 (15)	C15—C10—N5—O2	−25.6 (2)
C21—C16—C17—C18	−2.2 (3)	C11—C10—N5—O2	152.98 (16)
N8—C16—C17—C18	−179.96 (15)	C13—C12—N6—O4	−152.71 (17)
C16—C17—C18—N9	174.97 (14)	C11—C12—N6—O4	28.1 (2)
C16—C17—C18—C19	−0.9 (3)	C13—C12—N6—O5	26.7 (2)
C17—C18—C19—O12	178.22 (16)	C11—C12—N6—O5	−152.43 (17)
N9—C18—C19—O12	2.4 (2)	C15—C14—N7—O7	3.6 (3)
C17—C18—C19—C20	2.5 (2)	C13—C14—N7—O7	−175.25 (17)
N9—C18—C19—C20	−173.27 (14)	C15—C14—N7—O6	−178.29 (18)
O12—C19—C20—C21	−177.08 (16)	C13—C14—N7—O6	2.9 (3)
C18—C19—C20—C21	−1.4 (2)	C17—C16—N8—O9	−11.0 (3)
O12—C19—C20—N10	0.4 (2)	C21—C16—N8—O9	171.22 (16)
C18—C19—C20—N10	176.11 (14)	C17—C16—N8—O8	167.72 (17)
C19—C20—C21—C16	−1.3 (3)	C21—C16—N8—O8	−10.1 (3)
N10—C20—C21—C16	−178.86 (15)	C17—C18—N9—O11	145.15 (17)
C17—C16—C21—C20	3.2 (3)	C19—C18—N9—O11	−38.7 (2)
N8—C16—C21—C20	−179.00 (15)	C17—C18—N9—O10	−34.1 (2)
N2—C2—N1—C3	1.3 (2)	C19—C18—N9—O10	142.02 (16)
N2—C2—N1—C1	−177.51 (17)	C21—C20—N10—O13	−143.02 (19)
C4—C3—N1—C2	−1.3 (2)	C19—C20—N10—O13	39.3 (2)
C4—C3—N1—C1	177.47 (19)	C21—C20—N10—O14	37.2 (2)
N1—C2—N2—C4	−0.8 (2)	C19—C20—N10—O14	−140.47 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O11^i	0.93	2.36	3.074 (2)	134
C2—H2···O12^i	0.93	2.36	2.986 (2)	124
C5—H5B···O12^i	0.97	2.27	2.997 (2)	131
C7—H7···O7^i	0.93	2.41	3.256 (2)	151
C7—H7···O12^i	0.93	2.37	3.073 (2)	132
C8—H8···O6^i	0.93	2.53	3.205 (2)	129
C3—H3···O9^ii	0.93	2.55	3.403 (2)	153
C4—H4···O1^iii	0.93	2.46	3.210 (3)	138
C5—H5A···O3^iii	0.97	2.45	3.252 (2)	140
C6—H6···O3^iii	0.93	2.16	2.9494 (19)	142
C9—H9C···O4^iii	0.96	2.50	3.334 (2)	146
C21—H21···O10^iv	0.93	2.57	3.189 (2)	124

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