Promazinium picrate

In the title compound [systematic name: 3-(phenothia­zin-10-yl)propanaminium 2,4,6-trinitro­phenolate], C₁₇H₂₁N₂S⁺·C₆H₂N₃O₇⁻, the dihedral angle between the two outer aromatic rings of the phenothia­zine unit is 37.76 (6)°. The crystal packing is stabilized by N—H...O hydrogen bonds and several weak C—H...O contacts.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.046
• wR factor = 0.128
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O323   ..  O323    ..       2.84 Ang.

Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N36
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.07
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O362   ..  C5      ..       3.01 Ang.

   0 ALERT level A = In general: serious problem
   1 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
   4 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

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

3-(phenothiazin-10-yl)propanaminium 2,4,6-trinitrophenolate

Crystal data

C17H21N2S^+·C6H2N3O7^−	Z = 2
Mr = 513.52	F(000) = 536
Triclinic, P1	Dx = 1.424 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0611 (6) Å	Cell parameters from 21165 reflections
b = 10.2518 (7) Å	θ = 3.4–27.5°
c = 11.9841 (8) Å	µ = 0.19 mm^−1
α = 85.649 (6)°	T = 173 K
β = 78.414 (5)°	Plate, red
γ = 82.040 (5)°	0.42 × 0.36 × 0.19 mm
V = 1197.77 (13) Å^3

Data collection

Stoe IPDSII two-circle diffractometer	5489 independent reflections
Radiation source: fine-focus sealed tube	5037 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω scans	θmax = 27.6°, θmin = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −13→13
Tmin = 0.915, Tmax = 0.955	k = −11→13
22432 measured reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0689P)^2 + 0.5434P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
5489 reflections	Δρmax = 0.78 e Å^−3
349 parameters	Δρmin = −0.60 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (4)

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	Occ. (<1)
S1	0.35016 (4)	0.89530 (4)	0.10487 (3)	0.03213 (13)
N1	0.11730 (12)	0.74429 (11)	0.10612 (10)	0.0260 (3)
C1	0.03456 (15)	0.63790 (14)	0.10271 (14)	0.0296 (3)
H1A	0.0380	0.6188	0.0224	0.036*
H1B	−0.0619	0.6668	0.1375	0.036*
C2	0.08684 (15)	0.51178 (14)	0.16718 (12)	0.0271 (3)
H2A	0.1000	0.5340	0.2429	0.033*
H2B	0.0180	0.4492	0.1792	0.033*
C3	0.22179 (15)	0.44706 (14)	0.10000 (12)	0.0278 (3)
H3A	0.2031	0.3996	0.0370	0.033*
H3B	0.2791	0.5164	0.0659	0.033*
N4	0.29959 (12)	0.35177 (12)	0.17290 (10)	0.0260 (3)
H4	0.325 (2)	0.401 (2)	0.2249 (19)	0.048 (6)*
C5	0.42412 (17)	0.28149 (17)	0.10129 (15)	0.0375 (4)
H5A	0.4789	0.3462	0.0566	0.056*
H5B	0.3964	0.2253	0.0496	0.056*
H5C	0.4786	0.2269	0.1507	0.056*
C6	0.21454 (17)	0.25458 (16)	0.24167 (15)	0.0361 (3)
H6A	0.1336	0.3018	0.2884	0.054*
H6B	0.2684	0.1995	0.2913	0.054*
H6C	0.1858	0.1987	0.1904	0.054*
C11	0.22132 (14)	0.86721 (13)	0.22512 (13)	0.0267 (3)
C12	0.11752 (14)	0.79291 (13)	0.21426 (12)	0.0250 (3)
C13	0.01890 (16)	0.76910 (15)	0.31119 (13)	0.0313 (3)
H13	−0.0535	0.7210	0.3056	0.038*
C14	0.02584 (18)	0.81543 (17)	0.41615 (14)	0.0384 (4)
H14	−0.0412	0.7974	0.4815	0.046*
C15	0.12980 (19)	0.88765 (16)	0.42602 (14)	0.0389 (4)
H15	0.1343	0.9183	0.4978	0.047*
C16	0.22693 (17)	0.91456 (14)	0.33007 (14)	0.0326 (3)
H16	0.2973	0.9652	0.3359	0.039*
C21	0.25000 (14)	0.90970 (14)	−0.00247 (13)	0.0276 (3)
C22	0.14354 (14)	0.83110 (13)	0.00830 (12)	0.0251 (3)
C23	0.06887 (16)	0.84101 (15)	−0.07948 (13)	0.0320 (3)
H23	−0.0064	0.7923	−0.0723	0.038*
C24	0.10374 (18)	0.92163 (17)	−0.17761 (14)	0.0368 (3)
H24	0.0542	0.9247	−0.2376	0.044*
C25	0.21004 (18)	0.99710 (18)	−0.18793 (15)	0.0404 (4)
H25	0.2341	1.0511	−0.2550	0.048*
C26	0.28130 (16)	0.99331 (16)	−0.09946 (15)	0.0360 (3)
H26	0.3517	1.0478	−0.1048	0.043*
O31	0.67586 (15)	0.51651 (16)	0.64962 (11)	0.0531 (4)
C31	0.62354 (15)	0.43194 (15)	0.60901 (13)	0.0299 (3)
C32	0.67401 (15)	0.38807 (16)	0.49367 (13)	0.0306 (3)
C33	0.61944 (15)	0.29822 (16)	0.44334 (12)	0.0313 (3)
H33	0.6579	0.2739	0.3676	0.038*
C34	0.50654 (15)	0.24307 (15)	0.50524 (12)	0.0283 (3)
C35	0.45079 (15)	0.27560 (15)	0.61632 (12)	0.0286 (3)
H35	0.3741	0.2364	0.6575	0.034*
C36	0.50737 (15)	0.36549 (15)	0.66702 (12)	0.0278 (3)
N32	0.79403 (15)	0.44125 (17)	0.42406 (12)	0.0426 (4)
N34	0.44353 (15)	0.15127 (14)	0.45179 (12)	0.0359 (3)
N36	0.44213 (15)	0.39407 (16)	0.78398 (11)	0.0381 (3)
O321	0.8150 (3)	0.5470 (2)	0.4339 (2)	0.0501 (6)	0.662 (4)
O322	0.8744 (2)	0.3563 (2)	0.35780 (18)	0.0531 (7)	0.662 (4)
O323	0.8729 (6)	0.4930 (7)	0.4678 (5)	0.0656 (16)	0.338 (4)
O324	0.7899 (5)	0.4747 (6)	0.3193 (4)	0.0668 (18)	0.338 (4)
O341	0.49221 (15)	0.12584 (15)	0.35180 (11)	0.0489 (3)
O342	0.34322 (15)	0.10399 (15)	0.50797 (12)	0.0516 (4)
O361	0.34491 (17)	0.3351 (2)	0.82934 (12)	0.0718 (6)
O362	0.48880 (18)	0.46888 (17)	0.83649 (12)	0.0633 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.02157 (19)	0.0360 (2)	0.0402 (2)	−0.00729 (14)	−0.00616 (14)	−0.00374 (15)
N1	0.0283 (6)	0.0226 (5)	0.0296 (6)	−0.0083 (4)	−0.0088 (5)	0.0013 (4)
C1	0.0282 (7)	0.0255 (7)	0.0388 (8)	−0.0094 (5)	−0.0123 (6)	0.0023 (6)
C2	0.0280 (7)	0.0231 (6)	0.0305 (7)	−0.0076 (5)	−0.0043 (5)	0.0015 (5)
C3	0.0320 (7)	0.0278 (7)	0.0237 (6)	−0.0056 (5)	−0.0050 (5)	0.0013 (5)
N4	0.0288 (6)	0.0241 (6)	0.0253 (6)	−0.0042 (5)	−0.0046 (5)	−0.0021 (4)
C5	0.0358 (8)	0.0344 (8)	0.0390 (8)	0.0026 (6)	−0.0015 (7)	−0.0089 (6)
C6	0.0376 (8)	0.0283 (7)	0.0423 (8)	−0.0081 (6)	−0.0091 (7)	0.0087 (6)
C11	0.0255 (6)	0.0207 (6)	0.0342 (7)	−0.0004 (5)	−0.0078 (5)	−0.0028 (5)
C12	0.0238 (6)	0.0206 (6)	0.0303 (7)	−0.0001 (5)	−0.0061 (5)	−0.0016 (5)
C13	0.0285 (7)	0.0274 (7)	0.0355 (8)	−0.0019 (5)	−0.0026 (6)	0.0019 (6)
C14	0.0417 (9)	0.0353 (8)	0.0319 (8)	0.0049 (7)	0.0010 (6)	−0.0012 (6)
C15	0.0517 (10)	0.0314 (8)	0.0324 (8)	0.0075 (7)	−0.0113 (7)	−0.0076 (6)
C16	0.0381 (8)	0.0233 (7)	0.0394 (8)	0.0010 (6)	−0.0158 (6)	−0.0061 (6)
C21	0.0217 (6)	0.0253 (6)	0.0345 (7)	−0.0023 (5)	−0.0028 (5)	−0.0022 (5)
C22	0.0236 (6)	0.0209 (6)	0.0301 (7)	−0.0020 (5)	−0.0044 (5)	−0.0004 (5)
C23	0.0326 (7)	0.0297 (7)	0.0357 (8)	−0.0052 (6)	−0.0115 (6)	0.0020 (6)
C24	0.0388 (8)	0.0372 (8)	0.0342 (8)	−0.0018 (6)	−0.0111 (6)	0.0054 (6)
C25	0.0382 (8)	0.0398 (9)	0.0379 (8)	−0.0027 (7)	−0.0013 (7)	0.0114 (7)
C26	0.0276 (7)	0.0330 (8)	0.0440 (9)	−0.0064 (6)	−0.0001 (6)	0.0061 (6)
O31	0.0548 (8)	0.0749 (10)	0.0368 (6)	−0.0398 (7)	0.0003 (6)	−0.0155 (6)
C31	0.0272 (7)	0.0356 (8)	0.0291 (7)	−0.0091 (6)	−0.0075 (6)	−0.0005 (6)
C32	0.0247 (7)	0.0396 (8)	0.0273 (7)	−0.0083 (6)	−0.0040 (5)	0.0046 (6)
C33	0.0283 (7)	0.0402 (8)	0.0249 (6)	−0.0027 (6)	−0.0055 (5)	−0.0007 (6)
C34	0.0288 (7)	0.0313 (7)	0.0275 (7)	−0.0047 (6)	−0.0108 (6)	−0.0012 (5)
C35	0.0273 (7)	0.0321 (7)	0.0272 (7)	−0.0087 (6)	−0.0057 (5)	0.0028 (5)
C36	0.0296 (7)	0.0321 (7)	0.0220 (6)	−0.0065 (6)	−0.0041 (5)	−0.0005 (5)
N32	0.0344 (7)	0.0615 (10)	0.0321 (7)	−0.0171 (7)	−0.0010 (6)	0.0029 (6)
N34	0.0395 (7)	0.0372 (7)	0.0345 (7)	−0.0044 (6)	−0.0142 (6)	−0.0050 (5)
N36	0.0380 (7)	0.0511 (8)	0.0261 (6)	−0.0159 (6)	−0.0003 (5)	−0.0050 (6)
O321	0.0472 (14)	0.0453 (13)	0.0571 (14)	−0.0238 (10)	0.0001 (11)	0.0086 (10)
O322	0.0436 (12)	0.0630 (14)	0.0444 (12)	−0.0137 (10)	0.0174 (9)	−0.0064 (10)
O323	0.050 (3)	0.086 (4)	0.068 (3)	−0.043 (3)	−0.011 (2)	0.010 (3)
O324	0.049 (3)	0.110 (4)	0.036 (2)	−0.020 (3)	0.0064 (18)	0.015 (2)
O341	0.0511 (8)	0.0612 (8)	0.0389 (7)	−0.0074 (6)	−0.0129 (6)	−0.0186 (6)
O342	0.0552 (8)	0.0590 (8)	0.0486 (7)	−0.0322 (7)	−0.0112 (6)	−0.0048 (6)
O361	0.0588 (9)	0.1238 (16)	0.0381 (7)	−0.0518 (10)	0.0127 (7)	−0.0240 (8)
O362	0.0819 (11)	0.0740 (10)	0.0377 (7)	−0.0469 (9)	0.0120 (7)	−0.0231 (7)

Geometric parameters (Å, º)

S1—C11	1.7692 (15)	C16—H16	0.9500
S1—C21	1.7728 (15)	C21—C26	1.400 (2)
N1—C22	1.4207 (18)	C21—C22	1.4075 (19)
N1—C12	1.4240 (18)	C22—C23	1.400 (2)
N1—C1	1.4683 (17)	C23—C24	1.399 (2)
C1—C2	1.539 (2)	C23—H23	0.9500
C1—H1A	0.9900	C24—C25	1.385 (3)
C1—H1B	0.9900	C24—H24	0.9500
C2—C3	1.525 (2)	C25—C26	1.390 (3)
C2—H2A	0.9900	C25—H25	0.9500
C2—H2B	0.9900	C26—H26	0.9500
C3—N4	1.5045 (18)	O31—C31	1.2486 (19)
C3—H3A	0.9900	C31—C32	1.456 (2)
C3—H3B	0.9900	C31—C36	1.461 (2)
N4—C6	1.4942 (19)	C32—C33	1.368 (2)
N4—C5	1.4958 (19)	C32—N32	1.4697 (19)
N4—H4	0.93 (2)	C33—C34	1.391 (2)
C5—H5A	0.9800	C33—H33	0.9500
C5—H5B	0.9800	C34—C35	1.383 (2)
C5—H5C	0.9800	C34—N34	1.4551 (19)
C6—H6A	0.9800	C35—C36	1.383 (2)
C6—H6B	0.9800	C35—H35	0.9500
C6—H6C	0.9800	C36—N36	1.4563 (19)
C11—C16	1.396 (2)	N32—O321	1.151 (3)
C11—C12	1.406 (2)	N32—O323	1.229 (5)
C12—C13	1.398 (2)	N32—O324	1.283 (5)
C13—C14	1.396 (2)	N32—O322	1.302 (3)
C13—H13	0.9500	N34—O342	1.2328 (19)
C14—C15	1.391 (3)	N34—O341	1.2330 (19)
C14—H14	0.9500	N36—O362	1.2232 (19)
C15—C16	1.389 (2)	N36—O361	1.232 (2)
C15—H15	0.9500
C11—S1—C21	98.97 (7)	C16—C15—H15	120.3
C22—N1—C12	117.85 (11)	C14—C15—H15	120.3
C22—N1—C1	118.55 (12)	C15—C16—C11	120.07 (15)
C12—N1—C1	118.00 (12)	C15—C16—H16	120.0
N1—C1—C2	111.19 (11)	C11—C16—H16	120.0
N1—C1—H1A	109.4	C26—C21—C22	120.58 (14)
C2—C1—H1A	109.4	C26—C21—S1	120.19 (12)
N1—C1—H1B	109.4	C22—C21—S1	119.16 (11)
C2—C1—H1B	109.4	C23—C22—C21	118.08 (13)
H1A—C1—H1B	108.0	C23—C22—N1	122.78 (13)
C3—C2—C1	110.57 (12)	C21—C22—N1	119.13 (13)
C3—C2—H2A	109.5	C24—C23—C22	120.86 (14)
C1—C2—H2A	109.5	C24—C23—H23	119.6
C3—C2—H2B	109.5	C22—C23—H23	119.6
C1—C2—H2B	109.5	C25—C24—C23	120.45 (15)
H2A—C2—H2B	108.1	C25—C24—H24	119.8
N4—C3—C2	112.54 (11)	C23—C24—H24	119.8
N4—C3—H3A	109.1	C24—C25—C26	119.54 (15)
C2—C3—H3A	109.1	C24—C25—H25	120.2
N4—C3—H3B	109.1	C26—C25—H25	120.2
C2—C3—H3B	109.1	C25—C26—C21	120.38 (15)
H3A—C3—H3B	107.8	C25—C26—H26	119.8
C6—N4—C5	110.27 (12)	C21—C26—H26	119.8
C6—N4—C3	113.15 (12)	O31—C31—C32	122.29 (14)
C5—N4—C3	110.50 (12)	O31—C31—C36	126.20 (14)
C6—N4—H4	106.2 (14)	C32—C31—C36	111.51 (13)
C5—N4—H4	109.7 (14)	C33—C32—C31	125.16 (13)
C3—N4—H4	106.9 (14)	C33—C32—N32	115.91 (14)
N4—C5—H5A	109.5	C31—C32—N32	118.93 (14)
N4—C5—H5B	109.5	C32—C33—C34	118.72 (14)
H5A—C5—H5B	109.5	C32—C33—H33	120.6
N4—C5—H5C	109.5	C34—C33—H33	120.6
H5A—C5—H5C	109.5	C35—C34—C33	121.37 (14)
H5B—C5—H5C	109.5	C35—C34—N34	119.00 (13)
N4—C6—H6A	109.5	C33—C34—N34	119.62 (13)
N4—C6—H6B	109.5	C36—C35—C34	119.57 (13)
H6A—C6—H6B	109.5	C36—C35—H35	120.2
N4—C6—H6C	109.5	C34—C35—H35	120.2
H6A—C6—H6C	109.5	C35—C36—N36	115.89 (13)
H6B—C6—H6C	109.5	C35—C36—C31	123.64 (13)
C16—C11—C12	121.00 (14)	N36—C36—C31	120.46 (13)
C16—C11—S1	119.72 (12)	O323—N32—O324	117.0 (4)
C12—C11—S1	119.23 (11)	O321—N32—O322	124.95 (19)
C13—C12—C11	118.18 (13)	O321—N32—C32	121.09 (18)
C13—C12—N1	122.69 (13)	O323—N32—C32	121.4 (3)
C11—C12—N1	119.13 (13)	O324—N32—C32	117.4 (2)
C14—C13—C12	120.57 (15)	O322—N32—C32	113.85 (16)
C14—C13—H13	119.7	O342—N34—O341	123.15 (14)
C12—C13—H13	119.7	O342—N34—C34	118.59 (13)
C15—C14—C13	120.68 (15)	O341—N34—C34	118.25 (14)
C15—C14—H14	119.7	O362—N36—O361	121.77 (14)
C13—C14—H14	119.7	O362—N36—C36	120.07 (14)
C16—C15—C14	119.48 (15)	O361—N36—C36	118.03 (14)
C22—N1—C1—C2	143.41 (13)	C23—C24—C25—C26	−0.6 (3)
C12—N1—C1—C2	−63.50 (16)	C24—C25—C26—C21	2.7 (3)
N1—C1—C2—C3	−72.28 (15)	C22—C21—C26—C25	−1.8 (2)
C1—C2—C3—N4	161.37 (11)	S1—C21—C26—C25	174.89 (13)
C2—C3—N4—C6	50.38 (16)	O31—C31—C32—C33	−178.44 (17)
C2—C3—N4—C5	174.58 (12)	C36—C31—C32—C33	1.3 (2)
C21—S1—C11—C16	−147.01 (12)	O31—C31—C32—N32	2.4 (2)
C21—S1—C11—C12	35.43 (12)	C36—C31—C32—N32	−177.84 (14)
C16—C11—C12—C13	0.8 (2)	C31—C32—C33—C34	0.2 (2)
S1—C11—C12—C13	178.34 (10)	N32—C32—C33—C34	179.31 (14)
C16—C11—C12—N1	−178.73 (13)	C32—C33—C34—C35	−1.1 (2)
S1—C11—C12—N1	−1.20 (18)	C32—C33—C34—N34	177.57 (14)
C22—N1—C12—C13	136.69 (14)	C33—C34—C35—C36	0.5 (2)
C1—N1—C12—C13	−16.58 (19)	N34—C34—C35—C36	−178.22 (13)
C22—N1—C12—C11	−43.79 (18)	C34—C35—C36—N36	179.91 (14)
C1—N1—C12—C11	162.94 (13)	C34—C35—C36—C31	1.2 (2)
C11—C12—C13—C14	−1.5 (2)	O31—C31—C36—C35	177.76 (17)
N1—C12—C13—C14	178.01 (14)	C32—C31—C36—C35	−2.0 (2)
C12—C13—C14—C15	0.9 (2)	O31—C31—C36—N36	−0.9 (3)
C13—C14—C15—C16	0.5 (2)	C32—C31—C36—N36	179.37 (14)
C14—C15—C16—C11	−1.2 (2)	C33—C32—N32—O321	148.6 (2)
C12—C11—C16—C15	0.5 (2)	C31—C32—N32—O321	−32.2 (3)
S1—C11—C16—C15	−176.99 (12)	C33—C32—N32—O323	−160.1 (5)
C11—S1—C21—C26	147.76 (13)	C31—C32—N32—O323	19.1 (5)
C11—S1—C21—C22	−35.51 (13)	C33—C32—N32—O324	43.9 (4)
C26—C21—C22—C23	−1.2 (2)	C31—C32—N32—O324	−136.9 (3)
S1—C21—C22—C23	−177.87 (11)	C33—C32—N32—O322	−35.0 (2)
C26—C21—C22—N1	178.02 (13)	C31—C32—N32—O322	144.19 (18)
S1—C21—C22—N1	1.30 (18)	C35—C34—N34—O342	−0.9 (2)
C12—N1—C22—C23	−137.19 (14)	C33—C34—N34—O342	−179.68 (15)
C1—N1—C22—C23	15.9 (2)	C35—C34—N34—O341	178.16 (15)
C12—N1—C22—C21	43.67 (18)	C33—C34—N34—O341	−0.6 (2)
C1—N1—C22—C21	−163.20 (13)	C35—C36—N36—O362	177.37 (17)
C21—C22—C23—C24	3.2 (2)	C31—C36—N36—O362	−3.8 (3)
N1—C22—C23—C24	−175.93 (14)	C35—C36—N36—O361	1.5 (2)
C22—C23—C24—C25	−2.4 (3)	C31—C36—N36—O361	−179.72 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O31^i	0.93 (2)	1.78 (2)	2.6735 (17)	162 (2)
N4—H4···O362^i	0.93 (2)	2.41 (2)	2.9804 (18)	119.8 (17)
C2—H2B···O322^ii	0.99	2.53	3.280 (2)	132
C5—H5A···O362^i	0.98	2.46	3.008 (2)	115
C5—H5C···O341	0.98	2.57	3.439 (2)	148
C6—H6B···O341	0.98	2.50	3.389 (2)	150
C13—H13···O321^ii	0.95	2.59	3.336 (3)	136

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