1-Dimethyl­ammoniomethyl-6,8-dimethyl-2-phenyl-1,2-dihydro­imidazo[1,2-a][1,8]naphthyridine picrate monohydrate

In the title salt, C₂₁H₂₃N₄⁺·C₆H₂N₃O₇⁻·H₂O, the dimethyl­ammonio­methyl side chain is oriented nearly perpendicular to the imidazonaphthyridine moiety, which is nearly planar. In the crystal structure, inter­molecular N—H...O and O—H...O hydrogen bonds link two cations, two anions and two water mol­ecules into clusters, which further inter­act via weak C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.159
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.45
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C17
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C18
PLAT410_ALERT_2_C Short Intra H...H Contact  H19B   ..  H23     ..       1.97 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
   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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELX97.

1-Dimethylamminiomethyl-6,8-dimethyl-2-phenyl-1,2- dihydroimidazo[1,2-a][1,8]naphthyridine picrate monohydrate

Crystal data

C21H23N4^+·C6H2N3O7^−·H2O	Z = 2
Mr = 577.56	F(000) = 604
Triclinic, P1	Dx = 1.449 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 7.1449 (8) Å	Cell parameters from 25 reflections
b = 12.1932 (7) Å	θ = 15–50°
c = 15.790 (2) Å	µ = 0.92 mm^−1
α = 102.435 (4)°	T = 293 K
β = 98.938 (6)°	Prism, yellow
γ = 92.123 (5)°	0.50 × 0.40 × 0.35 mm
V = 1323.5 (2) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	4513 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
Graphite monochromator	θmax = 74.9°, θmin = 2.9°
ω–2θ scans	h = −8→8
Absorption correction: ψ scan (North et al., 1968)	k = −14→14
Tmin = 0.621, Tmax = 0.725	l = −8→19
6062 measured reflections	2 standard reflections every 100 reflections
5289 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.159	w = 1/[σ^2(Fo^2) + (0.0781P)^2 + 0.5163P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
5289 reflections	Δρmax = 0.35 e Å^−3
392 parameters	Δρmin = −0.28 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: 0.0061 (7)

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
O1	0.8216 (3)	0.76592 (15)	0.42303 (11)	0.0801 (6)
O2	0.6202 (4)	0.92609 (18)	0.37610 (12)	0.0882 (7)
O3	0.6414 (3)	1.08643 (15)	0.46388 (12)	0.0642 (5)
O4	0.9203 (4)	1.15161 (16)	0.75933 (12)	0.0831 (7)
O5	1.0699 (3)	1.02578 (17)	0.81226 (11)	0.0833 (7)
O6	1.0917 (4)	0.66101 (17)	0.63022 (12)	0.0888 (7)
O7	1.0864 (4)	0.64779 (19)	0.49395 (12)	0.0902 (7)
N1	0.6786 (3)	0.98780 (16)	0.44698 (11)	0.0478 (4)
N2	0.9797 (3)	1.05788 (17)	0.75086 (12)	0.0565 (5)
N3	1.0550 (3)	0.69738 (15)	0.56441 (11)	0.0504 (4)
C1	0.8579 (3)	0.83169 (17)	0.49562 (12)	0.0434 (4)
C2	0.7922 (3)	0.94428 (17)	0.51556 (12)	0.0399 (4)
C3	0.8325 (3)	1.01580 (17)	0.59650 (13)	0.0419 (4)
H3	0.7878	1.0874	0.6050	0.050*
C4	0.9395 (3)	0.98212 (17)	0.66577 (12)	0.0429 (4)
C5	1.0089 (3)	0.87610 (17)	0.65419 (12)	0.0426 (4)
H5	1.0794	0.8533	0.7012	0.051*
C6	0.9721 (3)	0.80567 (16)	0.57266 (12)	0.0402 (4)
N4	0.2745 (2)	0.41227 (13)	−0.03627 (9)	0.0380 (4)
N5	0.3628 (2)	0.37459 (13)	0.24799 (10)	0.0378 (4)
N6	0.3044 (2)	0.38232 (12)	0.09981 (9)	0.0321 (3)
N7	0.3909 (2)	0.61431 (13)	0.25502 (9)	0.0371 (4)
C7	0.3078 (3)	0.33695 (16)	0.01158 (11)	0.0359 (4)
C8	0.3386 (3)	0.22128 (17)	−0.01595 (12)	0.0441 (5)
H8	0.3393	0.1899	−0.0751	0.053*
C9	0.3668 (3)	0.15735 (17)	0.04354 (13)	0.0443 (4)
H9	0.3812	0.0809	0.0248	0.053*
C10	0.3750 (3)	0.20485 (16)	0.13568 (12)	0.0377 (4)
C11	0.4171 (3)	0.14408 (17)	0.20194 (14)	0.0440 (4)
C12	0.4287 (3)	0.20100 (18)	0.28821 (14)	0.0474 (5)
H12	0.4542	0.1621	0.3328	0.057*
C13	0.4032 (3)	0.31544 (18)	0.30975 (12)	0.0434 (4)
C14	0.3466 (2)	0.31962 (15)	0.16396 (11)	0.0333 (4)
C15	0.2609 (2)	0.49417 (14)	0.10573 (10)	0.0302 (3)
C16	0.2451 (2)	0.51010 (15)	0.02072 (10)	0.0324 (4)
C17	0.4531 (4)	0.0217 (2)	0.17961 (18)	0.0627 (6)
H17A	0.4790	−0.0054	0.2327	0.094*
H17B	0.5602	0.0122	0.1495	0.094*
H17C	0.3430	−0.0201	0.1423	0.094*
C18	0.4228 (4)	0.3793 (2)	0.40389 (13)	0.0584 (6)
H18A	0.3998	0.4567	0.4055	0.088*
H18B	0.5489	0.3748	0.4339	0.088*
H18C	0.3322	0.3471	0.4323	0.088*
C19	0.2163 (3)	0.56450 (15)	0.18862 (11)	0.0354 (4)
H19A	0.1387	0.5187	0.2150	0.042*
H19B	0.1422	0.6252	0.1745	0.042*
C20	0.3341 (4)	0.6660 (2)	0.34072 (13)	0.0568 (6)
H20A	0.4453	0.6975	0.3827	0.085*
H20B	0.2695	0.6094	0.3617	0.085*
H20C	0.2509	0.7244	0.3330	0.085*
C21	0.5087 (3)	0.69511 (18)	0.22342 (13)	0.0481 (5)
H21A	0.6175	0.7243	0.2676	0.072*
H21B	0.4348	0.7560	0.2118	0.072*
H21C	0.5501	0.6572	0.1704	0.072*
C22	0.2051 (2)	0.60994 (16)	−0.01627 (11)	0.0347 (4)
C23	0.1590 (3)	0.71293 (17)	0.03061 (13)	0.0435 (4)
H23	0.1528	0.7220	0.0901	0.052*
C24	0.1221 (3)	0.80192 (19)	−0.00943 (14)	0.0483 (5)
H24	0.0927	0.8701	0.0234	0.058*
C25	0.1285 (3)	0.7904 (2)	−0.09808 (15)	0.0529 (5)
H25	0.1023	0.8499	−0.1252	0.063*
C26	0.1745 (3)	0.6891 (2)	−0.14535 (14)	0.0529 (5)
H26	0.1806	0.6807	−0.2048	0.063*
C27	0.2115 (3)	0.60040 (19)	−0.10591 (12)	0.0434 (4)
H27	0.2414	0.5327	−0.1393	0.052*
O1W	0.7593 (3)	0.54611 (18)	0.32597 (14)	0.0799 (6)
H7N	0.462 (4)	0.553 (2)	0.2646 (17)	0.056 (7)*
H1W	0.801 (5)	0.605 (3)	0.368 (2)	0.079 (9)*
H2W	0.804 (7)	0.487 (4)	0.348 (3)	0.137 (17)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1255 (17)	0.0538 (10)	0.0421 (9)	0.0226 (10)	−0.0168 (10)	−0.0109 (7)
O2	0.1275 (18)	0.0791 (13)	0.0424 (9)	0.0267 (12)	−0.0212 (10)	0.0016 (9)
O3	0.0816 (12)	0.0522 (10)	0.0625 (10)	0.0130 (8)	0.0061 (9)	0.0239 (8)
O4	0.1304 (18)	0.0546 (11)	0.0520 (10)	0.0410 (11)	0.0028 (10)	−0.0115 (8)
O5	0.1215 (17)	0.0710 (12)	0.0410 (9)	0.0330 (12)	−0.0158 (10)	−0.0064 (8)
O6	0.150 (2)	0.0691 (13)	0.0494 (10)	0.0579 (13)	0.0103 (11)	0.0142 (9)
O7	0.1297 (19)	0.0863 (14)	0.0523 (10)	0.0602 (14)	0.0235 (11)	−0.0042 (10)
N1	0.0521 (10)	0.0525 (11)	0.0411 (9)	0.0028 (8)	0.0081 (7)	0.0153 (8)
N2	0.0725 (13)	0.0522 (11)	0.0372 (9)	0.0159 (9)	0.0041 (8)	−0.0045 (8)
N3	0.0616 (11)	0.0455 (10)	0.0409 (9)	0.0170 (8)	0.0083 (8)	0.0005 (7)
C1	0.0549 (11)	0.0394 (10)	0.0325 (9)	−0.0003 (8)	0.0063 (8)	0.0020 (7)
C2	0.0436 (10)	0.0430 (10)	0.0343 (9)	0.0012 (8)	0.0082 (7)	0.0102 (7)
C3	0.0482 (10)	0.0371 (10)	0.0408 (10)	0.0073 (8)	0.0114 (8)	0.0060 (8)
C4	0.0495 (10)	0.0423 (11)	0.0331 (9)	0.0076 (8)	0.0080 (8)	−0.0010 (8)
C5	0.0469 (10)	0.0458 (11)	0.0334 (9)	0.0094 (8)	0.0062 (7)	0.0045 (8)
C6	0.0462 (10)	0.0368 (10)	0.0375 (9)	0.0080 (8)	0.0120 (7)	0.0040 (7)
N4	0.0447 (8)	0.0423 (9)	0.0253 (7)	0.0023 (6)	0.0096 (6)	0.0015 (6)
N5	0.0442 (8)	0.0389 (8)	0.0291 (7)	0.0009 (6)	0.0067 (6)	0.0053 (6)
N6	0.0353 (7)	0.0349 (8)	0.0245 (7)	0.0025 (6)	0.0079 (5)	0.0010 (5)
N7	0.0551 (9)	0.0323 (8)	0.0225 (7)	0.0093 (7)	0.0083 (6)	0.0007 (5)
C7	0.0400 (9)	0.0397 (10)	0.0259 (8)	0.0006 (7)	0.0101 (6)	−0.0004 (7)
C8	0.0530 (11)	0.0430 (11)	0.0327 (9)	0.0063 (8)	0.0130 (8)	−0.0039 (8)
C9	0.0505 (11)	0.0351 (10)	0.0440 (10)	0.0079 (8)	0.0122 (8)	−0.0024 (8)
C10	0.0363 (9)	0.0368 (10)	0.0389 (9)	0.0032 (7)	0.0086 (7)	0.0042 (7)
C11	0.0431 (10)	0.0395 (11)	0.0497 (11)	0.0031 (8)	0.0064 (8)	0.0113 (8)
C12	0.0552 (12)	0.0447 (11)	0.0442 (11)	0.0020 (9)	0.0043 (9)	0.0172 (9)
C13	0.0506 (11)	0.0470 (11)	0.0331 (9)	−0.0009 (8)	0.0062 (8)	0.0116 (8)
C14	0.0321 (8)	0.0380 (9)	0.0292 (8)	0.0020 (7)	0.0069 (6)	0.0055 (7)
C15	0.0338 (8)	0.0314 (8)	0.0253 (7)	0.0048 (6)	0.0079 (6)	0.0031 (6)
C16	0.0331 (8)	0.0372 (9)	0.0254 (8)	0.0009 (7)	0.0075 (6)	0.0024 (6)
C17	0.0809 (17)	0.0423 (13)	0.0648 (15)	0.0126 (11)	0.0074 (12)	0.0137 (11)
C18	0.0865 (17)	0.0578 (14)	0.0312 (10)	0.0006 (12)	0.0069 (10)	0.0138 (9)
C19	0.0423 (9)	0.0378 (9)	0.0269 (8)	0.0090 (7)	0.0125 (7)	0.0037 (7)
C20	0.0909 (17)	0.0524 (12)	0.0248 (9)	0.0181 (11)	0.0168 (9)	−0.0031 (8)
C21	0.0597 (12)	0.0435 (11)	0.0378 (10)	−0.0037 (9)	0.0045 (9)	0.0055 (8)
C22	0.0331 (8)	0.0434 (10)	0.0276 (8)	−0.0012 (7)	0.0050 (6)	0.0087 (7)
C23	0.0503 (11)	0.0471 (11)	0.0337 (9)	0.0045 (8)	0.0082 (8)	0.0092 (8)
C24	0.0493 (11)	0.0455 (12)	0.0508 (11)	0.0061 (9)	0.0066 (9)	0.0135 (9)
C25	0.0501 (11)	0.0624 (14)	0.0519 (12)	0.0022 (10)	0.0042 (9)	0.0290 (11)
C26	0.0581 (12)	0.0705 (15)	0.0351 (10)	0.0013 (10)	0.0081 (9)	0.0231 (10)
C27	0.0471 (10)	0.0539 (12)	0.0300 (9)	0.0023 (8)	0.0092 (7)	0.0095 (8)
O1W	0.1047 (16)	0.0466 (10)	0.0714 (12)	0.0145 (10)	−0.0194 (11)	−0.0009 (9)

Geometric parameters (Å, º)

O1—C1	1.233 (2)	C11—C12	1.378 (3)
O2—N1	1.209 (2)	C11—C17	1.499 (3)
O3—N1	1.223 (2)	C12—C13	1.389 (3)
O4—N2	1.221 (3)	C12—H12	0.9300
O5—N2	1.223 (2)	C13—C18	1.505 (3)
O6—N3	1.211 (2)	C15—C16	1.385 (2)
O7—N3	1.205 (2)	C15—C19	1.489 (2)
N1—C2	1.456 (3)	C16—C22	1.478 (3)
N2—C4	1.438 (2)	C17—H17A	0.9600
N3—C6	1.456 (3)	C17—H17B	0.9600
C1—C2	1.453 (3)	C17—H17C	0.9600
C1—C6	1.457 (3)	C18—H18A	0.9600
C2—C3	1.365 (3)	C18—H18B	0.9600
C3—C4	1.381 (3)	C18—H18C	0.9600
C3—H3	0.9300	C19—H19A	0.9700
C4—C5	1.387 (3)	C19—H19B	0.9700
C5—C6	1.366 (3)	C20—H20A	0.9600
C5—H5	0.9300	C20—H20B	0.9600
N4—C7	1.315 (2)	C20—H20C	0.9600
N4—C16	1.375 (2)	C21—H21A	0.9600
N5—C14	1.337 (2)	C21—H21B	0.9600
N5—C13	1.336 (2)	C21—H21C	0.9600
N6—C7	1.388 (2)	C22—C23	1.393 (3)
N6—C15	1.397 (2)	C22—C27	1.403 (2)
N6—C14	1.399 (2)	C23—C24	1.383 (3)
N7—C21	1.486 (3)	C23—H23	0.9300
N7—C20	1.488 (2)	C24—C25	1.385 (3)
N7—C19	1.512 (2)	C24—H24	0.9300
N7—H7N	0.95 (3)	C25—C26	1.379 (4)
C7—C8	1.420 (3)	C25—H25	0.9300
C8—C9	1.341 (3)	C26—C27	1.374 (3)
C8—H8	0.9300	C26—H26	0.9300
C9—C10	1.437 (3)	C27—H27	0.9300
C9—H9	0.9300	O1W—H1W	0.87 (4)
C10—C14	1.407 (3)	O1W—H2W	0.91 (5)
C10—C11	1.410 (3)
O2—N1—O3	121.70 (19)	N5—C14—N6	117.18 (16)
O2—N1—C2	119.93 (19)	N5—C14—C10	124.89 (17)
O3—N1—C2	118.35 (18)	N6—C14—C10	117.90 (15)
O5—N2—O4	122.43 (19)	C16—C15—N6	105.27 (14)
O5—N2—C4	118.93 (19)	C16—C15—C19	132.71 (16)
O4—N2—C4	118.63 (19)	N6—C15—C19	121.39 (15)
O7—N3—O6	122.4 (2)	N4—C16—C15	110.49 (16)
O7—N3—C6	119.88 (19)	N4—C16—C22	117.65 (14)
O6—N3—C6	117.73 (17)	C15—C16—C22	131.86 (16)
O1—C1—C2	124.7 (2)	C11—C17—H17A	109.5
O1—C1—C6	124.0 (2)	C11—C17—H17B	109.5
C2—C1—C6	111.37 (16)	H17A—C17—H17B	109.5
C3—C2—C1	123.93 (18)	C11—C17—H17C	109.5
C3—C2—N1	115.88 (18)	H17A—C17—H17C	109.5
C1—C2—N1	120.19 (17)	H17B—C17—H17C	109.5
C2—C3—C4	120.14 (18)	C13—C18—H18A	109.5
C2—C3—H3	119.9	C13—C18—H18B	109.5
C4—C3—H3	119.9	H18A—C18—H18B	109.5
C3—C4—C5	120.77 (18)	C13—C18—H18C	109.5
C3—C4—N2	119.61 (18)	H18A—C18—H18C	109.5
C5—C4—N2	119.62 (18)	H18B—C18—H18C	109.5
C6—C5—C4	118.96 (18)	C15—C19—N7	113.47 (14)
C6—C5—H5	120.5	C15—C19—H19A	108.9
C4—C5—H5	120.5	N7—C19—H19A	108.9
C5—C6—C1	124.79 (18)	C15—C19—H19B	108.9
C5—C6—N3	116.09 (18)	N7—C19—H19B	108.9
C1—C6—N3	119.12 (16)	H19A—C19—H19B	107.7
C7—N4—C16	106.31 (14)	N7—C20—H20A	109.5
C14—N5—C13	117.63 (16)	N7—C20—H20B	109.5
C7—N6—C15	106.40 (14)	H20A—C20—H20B	109.5
C7—N6—C14	121.72 (15)	N7—C20—H20C	109.5
C15—N6—C14	131.84 (14)	H20A—C20—H20C	109.5
C21—N7—C20	112.00 (16)	H20B—C20—H20C	109.5
C21—N7—C19	112.59 (14)	N7—C21—H21A	109.5
C20—N7—C19	109.74 (16)	N7—C21—H21B	109.5
C21—N7—H7N	109.5 (16)	H21A—C21—H21B	109.5
C20—N7—H7N	106.4 (16)	N7—C21—H21C	109.5
C19—N7—H7N	106.3 (15)	H21A—C21—H21C	109.5
N4—C7—N6	111.51 (15)	H21B—C21—H21C	109.5
N4—C7—C8	128.91 (16)	C23—C22—C27	117.06 (18)
N6—C7—C8	119.54 (17)	C23—C22—C16	125.16 (15)
C9—C8—C7	119.79 (17)	C27—C22—C16	117.78 (17)
C9—C8—H8	120.1	C24—C23—C22	121.39 (18)
C7—C8—H8	120.1	C24—C23—H23	119.3
C8—C9—C10	121.18 (18)	C22—C23—H23	119.3
C8—C9—H9	119.4	C23—C24—C25	120.5 (2)
C10—C9—H9	119.4	C23—C24—H24	119.7
C14—C10—C11	116.47 (17)	C25—C24—H24	119.7
C14—C10—C9	119.58 (17)	C26—C25—C24	118.8 (2)
C11—C10—C9	123.92 (18)	C26—C25—H25	120.6
C12—C11—C10	118.09 (18)	C24—C25—H25	120.6
C12—C11—C17	120.8 (2)	C25—C26—C27	120.95 (19)
C10—C11—C17	121.13 (19)	C25—C26—H26	119.5
C11—C12—C13	121.19 (19)	C27—C26—H26	119.5
C11—C12—H12	119.4	C26—C27—C22	121.3 (2)
C13—C12—H12	119.4	C26—C27—H27	119.4
N5—C13—C12	121.68 (18)	C22—C27—H27	119.4
N5—C13—C18	116.70 (19)	H1W—O1W—H2W	104 (3)
C12—C13—C18	121.60 (18)
O1—C1—C2—C3	179.5 (2)	C10—C11—C12—C13	−1.1 (3)
C6—C1—C2—C3	−0.2 (3)	C17—C11—C12—C13	177.4 (2)
O1—C1—C2—N1	−1.5 (3)	C14—N5—C13—C12	0.4 (3)
C6—C1—C2—N1	178.78 (17)	C14—N5—C13—C18	179.36 (18)
O2—N1—C2—C3	−172.3 (2)	C11—C12—C13—N5	1.3 (3)
O3—N1—C2—C3	6.0 (3)	C11—C12—C13—C18	−177.7 (2)
O2—N1—C2—C1	8.6 (3)	C13—N5—C14—N6	180.00 (16)
O3—N1—C2—C1	−173.06 (19)	C13—N5—C14—C10	−2.2 (3)
C1—C2—C3—C4	−0.9 (3)	C7—N6—C14—N5	171.82 (15)
N1—C2—C3—C4	−179.96 (18)	C15—N6—C14—N5	−5.3 (3)
C2—C3—C4—C5	0.6 (3)	C7—N6—C14—C10	−6.1 (2)
C2—C3—C4—N2	−179.50 (19)	C15—N6—C14—C10	176.71 (16)
O5—N2—C4—C3	177.9 (2)	C11—C10—C14—N5	2.3 (3)
O4—N2—C4—C3	−1.3 (3)	C9—C10—C14—N5	−175.53 (17)
O5—N2—C4—C5	−2.2 (3)	C11—C10—C14—N6	−179.92 (16)
O4—N2—C4—C5	178.7 (2)	C9—C10—C14—N6	2.3 (2)
C3—C4—C5—C6	0.9 (3)	C7—N6—C15—C16	−1.33 (18)
N2—C4—C5—C6	−179.00 (19)	C14—N6—C15—C16	176.14 (17)
C4—C5—C6—C1	−2.2 (3)	C7—N6—C15—C19	170.63 (15)
C4—C5—C6—N3	177.81 (18)	C14—N6—C15—C19	−11.9 (3)
O1—C1—C6—C5	−177.9 (2)	C7—N4—C16—C15	0.0 (2)
C2—C1—C6—C5	1.8 (3)	C7—N4—C16—C22	179.65 (15)
O1—C1—C6—N3	2.0 (3)	N6—C15—C16—N4	0.85 (19)
C2—C1—C6—N3	−178.20 (17)	C19—C15—C16—N4	−169.80 (18)
O7—N3—C6—C5	−154.8 (2)	N6—C15—C16—C22	−178.73 (17)
O6—N3—C6—C5	24.6 (3)	C19—C15—C16—C22	10.6 (3)
O7—N3—C6—C1	25.3 (3)	C16—C15—C19—N7	−109.0 (2)
O6—N3—C6—C1	−155.4 (2)	N6—C15—C19—N7	81.5 (2)
C16—N4—C7—N6	−0.9 (2)	C21—N7—C19—C15	64.3 (2)
C16—N4—C7—C8	176.92 (19)	C20—N7—C19—C15	−170.19 (16)
C15—N6—C7—N4	1.4 (2)	N4—C16—C22—C23	175.25 (17)
C14—N6—C7—N4	−176.35 (15)	C15—C16—C22—C23	−5.2 (3)
C15—N6—C7—C8	−176.61 (16)	N4—C16—C22—C27	−3.9 (2)
C14—N6—C7—C8	5.6 (3)	C15—C16—C22—C27	175.66 (18)
N4—C7—C8—C9	−178.6 (2)	C27—C22—C23—C24	−0.3 (3)
N6—C7—C8—C9	−1.0 (3)	C16—C22—C23—C24	−179.46 (18)
C7—C8—C9—C10	−2.8 (3)	C22—C23—C24—C25	0.6 (3)
C8—C9—C10—C14	2.2 (3)	C23—C24—C25—C26	−0.7 (3)
C8—C9—C10—C11	−175.45 (19)	C24—C25—C26—C27	0.7 (3)
C14—C10—C11—C12	−0.6 (3)	C25—C26—C27—C22	−0.4 (3)
C9—C10—C11—C12	177.16 (19)	C23—C22—C27—C26	0.2 (3)
C14—C10—C11—C17	−179.02 (19)	C16—C22—C27—C26	179.46 (18)
C9—C10—C11—C17	−1.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7N···O1W	0.95 (3)	2.20 (3)	2.919 (3)	132 (2)
N7—H7N···N5	0.95 (3)	2.21 (3)	2.899 (2)	129 (2)
O1W—H1W···O1	0.87 (4)	1.96 (4)	2.768 (3)	154 (3)
O1W—H2W···O6^i	0.91 (5)	2.06 (5)	2.952 (3)	167 (4)
C25—H25···O5^ii	0.93	2.55	3.474 (3)	173
C26—H26···O6^ii	0.93	2.54	3.440 (3)	163
C20—H20C···O4^iii	0.96	2.54	3.416 (3)	152
C21—H21A···O1	0.96	2.59	3.489 (3)	156

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