Supra­molecular hydrogen-bonding networks in bis­(adeninium) phthalate phthalic acid 1.45-hydrate

In the title compound, 2C₅H₆N₅⁺·C₈H₄O₄²⁻·C₈H₆O₄·1.45H₂O, the asymmetric unit comprises two adeninium cations, two half phthalate anions with crystallographic C₂ symmetry, one neutral phthalic acid mol­ecule, and one fully occupied and one partially occupied site (0.45) for water mol­ecules. The adeninium cations form N—H...O hydrogen bonds with the phthalate anions. The cations also form infinite one-dimensional polymeric ribbons via N—H...N inter­actions. In the crystal packing, hydrogen-bonded columns of cations, anions and phthalate anions extend parallel to the c axis. The water mol­ecules crosslink adjacent columns into hydrogen-bonded layers.

Computing details

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: SHELXTL/PC (Sheldrick, 1990) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97.

bis(adeninium) phthalate phthalic acid 1.45-hydrate

Crystal data

2C5H6N5^+·C8H4O4^2^−·C8H6O4·1.45H2O	F(000) = 2612.1
Mr = 628.65	Dx = 1.486 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 7507 reflections
a = 7.0100 (5) Å	θ = 2.5–27.5°
b = 33.052 (2) Å	µ = 0.12 mm^−1
c = 24.2496 (17) Å	T = 293 K
V = 5618.4 (7) Å^3	Block, colourless
Z = 8	0.19 × 0.17 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4499 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 25.0°, θmin = 1.7°
ω scans	h = −8→8
50712 measured reflections	k = −39→39
4961 independent reflections	l = −28→28

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0485P)^2 + 2.4152P] where P = (Fo^2 + 2Fc^2)/3
4961 reflections	(Δ/σ)max = 0.001
472 parameters	Δρmax = 0.27 e Å^−3
4 restraints	Δρmin = −0.20 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.5854 (2)	0.63643 (5)	0.69324 (6)	0.0371 (4)
C2	0.5315 (2)	0.67455 (4)	0.72261 (6)	0.0333 (3)
C3	0.5612 (2)	0.71129 (5)	0.69591 (7)	0.0389 (4)
H3	0.6020	0.7115	0.6594	0.047*
C4	0.5309 (2)	0.74746 (5)	0.72305 (7)	0.0439 (4)
H4	0.5521	0.7718	0.7049	0.053*
O1	0.6818 (2)	0.61093 (4)	0.72005 (5)	0.0599 (4)
O2	0.5425 (2)	0.63196 (4)	0.64362 (4)	0.0508 (3)
C5	0.6074 (2)	0.68901 (5)	0.30215 (6)	0.0373 (4)
C6	0.5388 (2)	0.72766 (4)	0.27660 (6)	0.0329 (3)
C7	0.5711 (2)	0.76419 (5)	0.30321 (7)	0.0408 (4)
H7	0.6177	0.7643	0.3391	0.049*
C8	0.5342 (2)	0.80036 (5)	0.27662 (7)	0.0470 (4)
H8A	0.5555	0.8247	0.2947	0.056*
O3	0.7061 (2)	0.66571 (4)	0.27305 (5)	0.0593 (4)
O4	0.57341 (19)	0.68209 (4)	0.35207 (4)	0.0485 (3)
C9	0.1690 (3)	0.64747 (5)	0.55479 (7)	0.0440 (4)
C10	0.0225 (3)	0.67218 (5)	0.52441 (6)	0.0397 (4)
C11	−0.1510 (3)	0.67834 (6)	0.55067 (8)	0.0514 (5)
H11	−0.1723	0.6670	0.5852	0.062*
C12	−0.2918 (3)	0.70108 (6)	0.52600 (8)	0.0573 (5)
H12	−0.4075	0.7050	0.5440	0.069*
C13	−0.2625 (3)	0.71805 (6)	0.47484 (8)	0.0538 (5)
H13	−0.3582	0.7333	0.4583	0.065*
C14	−0.0911 (3)	0.71237 (5)	0.44834 (7)	0.0457 (4)
H14	−0.0714	0.7239	0.4138	0.055*
C15	0.0533 (2)	0.68956 (5)	0.47258 (6)	0.0377 (4)
C16	0.2374 (2)	0.68309 (5)	0.44358 (6)	0.0388 (4)
O5	0.1742 (3)	0.61115 (4)	0.55338 (6)	0.0723 (5)
O6	0.2806 (2)	0.67018 (4)	0.58560 (5)	0.0537 (3)
H6	0.371 (4)	0.6559 (8)	0.6060 (11)	0.098 (9)*
O7	0.34442 (19)	0.65565 (4)	0.45513 (6)	0.0577 (4)
O8	0.2722 (2)	0.70943 (4)	0.40411 (5)	0.0519 (3)
H8	0.377 (4)	0.7014 (7)	0.3871 (10)	0.078 (8)*
C22	0.6827 (3)	0.60099 (6)	0.44488 (7)	0.0477 (4)
H22	0.6684	0.6235	0.4675	0.057*
C24	0.7242 (2)	0.53533 (5)	0.43201 (7)	0.0421 (4)
C25	0.7202 (3)	0.53809 (5)	0.37511 (7)	0.0419 (4)
C26	0.6955 (2)	0.57644 (5)	0.35165 (7)	0.0415 (4)
C28	0.7573 (3)	0.47633 (6)	0.39350 (7)	0.0510 (5)
H28	0.7737	0.4485	0.3901	0.061*
N21	0.6757 (2)	0.60705 (4)	0.38999 (6)	0.0428 (3)
H21	0.654 (3)	0.6328 (7)	0.3787 (9)	0.063 (6)*
N23	0.7080 (2)	0.56618 (5)	0.46895 (6)	0.0483 (4)
N27	0.7411 (2)	0.50069 (4)	0.35094 (6)	0.0486 (4)
N29	0.7477 (2)	0.49560 (5)	0.44302 (6)	0.0481 (4)
H29	0.759 (3)	0.4856 (7)	0.4783 (9)	0.066 (6)*
N30	0.6889 (3)	0.58450 (5)	0.29864 (6)	0.0533 (4)
H301	0.685 (3)	0.6107 (8)	0.2880 (9)	0.070 (7)*
H302	0.716 (3)	0.5655 (6)	0.2747 (8)	0.050 (5)*
C32	0.7465 (3)	0.50949 (5)	0.71608 (7)	0.0505 (5)
H32	0.7425	0.5170	0.7530	0.061*
C34	0.7801 (2)	0.46369 (5)	0.65045 (7)	0.0387 (4)
C35	0.7599 (2)	0.49169 (5)	0.60869 (6)	0.0366 (3)
C36	0.7271 (2)	0.53230 (5)	0.62354 (6)	0.0386 (4)
C38	0.7983 (3)	0.43451 (5)	0.57031 (7)	0.0444 (4)
H38	0.8119	0.4143	0.5439	0.053*
N31	0.7239 (2)	0.53911 (4)	0.67878 (6)	0.0444 (4)
H31	0.706 (4)	0.5654 (6)	0.6913 (10)	0.089 (8)*
N33	0.7737 (2)	0.47103 (4)	0.70546 (6)	0.0494 (4)
N37	0.7711 (2)	0.47273 (4)	0.55777 (5)	0.0427 (3)
N39	0.8046 (2)	0.42725 (4)	0.62520 (6)	0.0430 (3)
H39	0.829 (3)	0.4036 (7)	0.6430 (8)	0.058 (6)*
N40	0.6988 (3)	0.56279 (5)	0.58987 (6)	0.0520 (4)
H401	0.670 (3)	0.5864 (7)	0.6031 (8)	0.059 (6)*
H402	0.704 (3)	0.5597 (6)	0.5510 (9)	0.061 (6)*
O1W	0.9041 (3)	0.35656 (4)	0.67902 (6)	0.0587 (4)
H1W	0.824 (5)	0.3480 (10)	0.7030 (13)	0.108 (11)*
H2W	1.012 (6)	0.3530 (11)	0.6923 (16)	0.151 (16)*
O2W	1.0978 (8)	0.59414 (17)	0.6871 (2)	0.104 (2)	0.454 (6)
H3W	1.194 (7)	0.605 (2)	0.706 (3)	0.14 (3)*	0.454 (6)
H4W	0.992 (7)	0.591 (4)	0.707 (3)	0.24 (7)*	0.454 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0429 (9)	0.0348 (8)	0.0337 (8)	0.0032 (7)	−0.0003 (7)	0.0015 (6)
C2	0.0337 (8)	0.0308 (7)	0.0352 (8)	0.0004 (6)	−0.0037 (6)	0.0014 (6)
C3	0.0398 (9)	0.0379 (8)	0.0392 (8)	−0.0003 (7)	−0.0022 (7)	0.0076 (7)
C4	0.0449 (10)	0.0293 (8)	0.0576 (10)	−0.0024 (7)	−0.0087 (8)	0.0079 (7)
O1	0.0904 (10)	0.0429 (7)	0.0465 (7)	0.0276 (7)	−0.0217 (7)	−0.0100 (6)
O2	0.0717 (9)	0.0484 (7)	0.0323 (6)	0.0172 (6)	−0.0052 (6)	−0.0045 (5)
C5	0.0403 (9)	0.0377 (8)	0.0340 (8)	0.0036 (7)	0.0051 (7)	0.0003 (6)
C6	0.0335 (8)	0.0324 (8)	0.0328 (7)	0.0012 (6)	0.0065 (6)	−0.0002 (6)
C7	0.0384 (9)	0.0426 (9)	0.0413 (9)	0.0005 (7)	0.0025 (7)	−0.0088 (7)
C8	0.0439 (10)	0.0309 (8)	0.0662 (11)	−0.0016 (7)	0.0075 (8)	−0.0096 (7)
O3	0.0851 (10)	0.0430 (7)	0.0498 (7)	0.0247 (7)	0.0280 (7)	0.0095 (6)
O4	0.0647 (8)	0.0486 (7)	0.0320 (6)	0.0125 (6)	0.0077 (6)	0.0052 (5)
C9	0.0573 (11)	0.0399 (9)	0.0347 (8)	−0.0002 (8)	0.0045 (8)	0.0025 (7)
C10	0.0477 (9)	0.0346 (8)	0.0367 (8)	−0.0043 (7)	0.0018 (7)	−0.0043 (6)
C11	0.0561 (11)	0.0533 (11)	0.0448 (10)	−0.0037 (9)	0.0109 (9)	−0.0038 (8)
C12	0.0451 (11)	0.0648 (12)	0.0620 (12)	0.0014 (9)	0.0108 (9)	−0.0146 (10)
C13	0.0455 (10)	0.0559 (11)	0.0599 (12)	0.0095 (9)	−0.0082 (9)	−0.0107 (9)
C14	0.0497 (10)	0.0459 (9)	0.0416 (9)	0.0023 (8)	−0.0057 (8)	−0.0021 (7)
C15	0.0422 (9)	0.0353 (8)	0.0357 (8)	−0.0017 (7)	−0.0012 (7)	−0.0036 (6)
C16	0.0456 (9)	0.0364 (8)	0.0344 (8)	0.0002 (7)	−0.0008 (7)	−0.0021 (7)
O5	0.1073 (13)	0.0387 (8)	0.0708 (10)	0.0008 (8)	−0.0185 (9)	0.0078 (6)
O6	0.0638 (9)	0.0461 (7)	0.0513 (8)	0.0066 (6)	−0.0143 (7)	−0.0013 (6)
O7	0.0552 (8)	0.0592 (8)	0.0586 (8)	0.0159 (7)	0.0110 (6)	0.0147 (6)
O8	0.0615 (8)	0.0478 (7)	0.0464 (7)	0.0089 (6)	0.0164 (6)	0.0090 (6)
C22	0.0549 (11)	0.0468 (10)	0.0413 (9)	0.0068 (8)	−0.0039 (8)	−0.0043 (8)
C24	0.0442 (9)	0.0496 (10)	0.0324 (8)	0.0011 (8)	−0.0009 (7)	0.0035 (7)
C25	0.0482 (10)	0.0399 (9)	0.0376 (9)	−0.0024 (7)	−0.0003 (7)	−0.0010 (7)
C26	0.0475 (10)	0.0400 (9)	0.0369 (9)	−0.0032 (7)	−0.0029 (7)	0.0010 (7)
C28	0.0692 (12)	0.0421 (10)	0.0418 (10)	0.0010 (9)	0.0009 (9)	0.0011 (8)
N21	0.0523 (9)	0.0364 (8)	0.0397 (8)	0.0037 (7)	−0.0031 (6)	−0.0001 (6)
N23	0.0607 (10)	0.0471 (8)	0.0372 (8)	0.0077 (7)	−0.0028 (7)	0.0012 (6)
N27	0.0680 (10)	0.0380 (7)	0.0399 (8)	−0.0009 (7)	0.0011 (7)	−0.0039 (6)
N29	0.0644 (10)	0.0452 (8)	0.0346 (8)	0.0036 (7)	−0.0005 (7)	0.0069 (6)
N30	0.0900 (13)	0.0377 (8)	0.0321 (8)	−0.0024 (8)	−0.0015 (8)	0.0022 (7)
C32	0.0772 (13)	0.0439 (10)	0.0305 (8)	0.0043 (9)	−0.0008 (8)	−0.0003 (7)
C34	0.0455 (9)	0.0340 (8)	0.0367 (8)	0.0001 (7)	0.0004 (7)	0.0007 (7)
C35	0.0440 (9)	0.0340 (8)	0.0318 (8)	0.0005 (7)	0.0014 (7)	−0.0011 (6)
C36	0.0479 (9)	0.0355 (8)	0.0325 (8)	0.0013 (7)	0.0010 (7)	−0.0006 (7)
C38	0.0580 (11)	0.0331 (8)	0.0422 (9)	0.0025 (8)	0.0016 (8)	−0.0068 (7)
N31	0.0673 (10)	0.0345 (7)	0.0314 (7)	0.0055 (7)	−0.0004 (7)	−0.0024 (6)
N33	0.0746 (11)	0.0385 (8)	0.0349 (7)	0.0034 (7)	−0.0013 (7)	0.0026 (6)
N37	0.0582 (9)	0.0370 (7)	0.0328 (7)	0.0025 (6)	0.0016 (6)	−0.0043 (6)
N39	0.0566 (9)	0.0299 (7)	0.0426 (8)	0.0015 (6)	0.0007 (7)	0.0015 (6)
N40	0.0904 (13)	0.0334 (8)	0.0323 (8)	0.0107 (8)	0.0023 (8)	0.0003 (6)
O1W	0.0657 (10)	0.0528 (8)	0.0574 (8)	0.0024 (7)	0.0051 (8)	0.0179 (6)
O2W	0.097 (4)	0.116 (4)	0.097 (3)	−0.003 (3)	−0.021 (3)	−0.042 (3)

Geometric parameters (Å, º)

C1—O2	1.2488 (19)	C22—N21	1.347 (2)
C1—O1	1.2608 (19)	C22—H22	0.9300
C1—C2	1.496 (2)	C24—N29	1.350 (2)
C2—C3	1.392 (2)	C24—N23	1.362 (2)
C2—C2^i	1.400 (3)	C24—C25	1.383 (2)
C3—C4	1.381 (2)	C25—N27	1.376 (2)
C3—H3	0.9300	C25—C26	1.400 (2)
C4—C4^i	1.377 (4)	C26—N30	1.314 (2)
C4—H4	0.9300	C26—N21	1.381 (2)
C5—O3	1.2528 (19)	C28—N27	1.314 (2)
C5—O4	1.2548 (19)	C28—N29	1.361 (2)
C5—C6	1.499 (2)	C28—H28	0.9300
C6—C7	1.388 (2)	N21—H21	0.91 (2)
C6—C6^ii	1.400 (3)	N29—H29	0.92 (2)
C7—C8	1.383 (2)	N30—H301	0.90 (2)
C7—H7	0.9300	N30—H302	0.88 (2)
C8—C8^ii	1.377 (4)	C32—N33	1.311 (2)
C8—H8A	0.9300	C32—N31	1.342 (2)
C9—O5	1.202 (2)	C32—H32	0.9300
C9—O6	1.317 (2)	C34—N33	1.357 (2)
C9—C10	1.505 (2)	C34—N39	1.362 (2)
C10—C11	1.388 (3)	C34—C35	1.379 (2)
C10—C15	1.399 (2)	C35—N37	1.387 (2)
C11—C12	1.378 (3)	C35—C36	1.409 (2)
C11—H11	0.9300	C36—N40	1.312 (2)
C12—C13	1.377 (3)	C36—N31	1.358 (2)
C12—H12	0.9300	C38—N37	1.313 (2)
C13—C14	1.376 (3)	C38—N39	1.353 (2)
C13—H13	0.9300	C38—H38	0.9300
C14—C15	1.392 (2)	N31—H31	0.930 (17)
C14—H14	0.9300	N39—H39	0.91 (2)
C15—C16	1.485 (2)	N40—H401	0.87 (2)
C16—O7	1.210 (2)	N40—H402	0.95 (2)
C16—O8	1.316 (2)	O1W—H1W	0.86 (3)
O6—H6	0.93 (3)	O1W—H2W	0.83 (4)
O8—H8	0.88 (3)	O2W—H3W	0.894 (11)
C22—N23	1.302 (2)	O2W—H4W	0.896 (10)
O2—C1—O1	123.13 (15)	N21—C22—H22	117.3
O2—C1—C2	119.83 (14)	N29—C24—N23	127.47 (15)
O1—C1—C2	116.94 (14)	N29—C24—C25	105.30 (15)
C3—C2—C2^i	119.25 (9)	N23—C24—C25	127.23 (16)
C3—C2—C1	118.39 (14)	N27—C25—C24	111.32 (15)
C2^i—C2—C1	122.11 (8)	N27—C25—C26	130.81 (15)
C4—C3—C2	120.68 (15)	C24—C25—C26	117.87 (15)
C4—C3—H3	119.7	N30—C26—N21	120.44 (16)
C2—C3—H3	119.7	N30—C26—C25	125.84 (16)
C4^i—C4—C3	120.07 (10)	N21—C26—C25	113.71 (14)
C4^i—C4—H4	120.0	N27—C28—N29	113.70 (16)
C3—C4—H4	120.0	N27—C28—H28	123.1
O3—C5—O4	122.44 (15)	N29—C28—H28	123.1
O3—C5—C6	117.92 (13)	C22—N21—C26	123.55 (15)
O4—C5—C6	119.54 (14)	C22—N21—H21	116.3 (13)
C7—C6—C6^ii	119.46 (10)	C26—N21—H21	120.1 (13)
C7—C6—C5	119.81 (14)	C22—N23—C24	112.22 (14)
C6^ii—C6—C5	120.36 (9)	C28—N27—C25	103.02 (14)
C8—C7—C6	120.33 (16)	C24—N29—C28	106.67 (15)
C8—C7—H7	119.8	C24—N29—H29	122.8 (13)
C6—C7—H7	119.8	C28—N29—H29	130.5 (13)
C8^ii—C8—C7	120.16 (10)	C26—N30—H301	118.3 (14)
C8^ii—C8—H8A	119.9	C26—N30—H302	119.7 (13)
C7—C8—H8A	119.9	H301—N30—H302	120.3 (19)
O5—C9—O6	124.59 (18)	N33—C32—N31	126.29 (16)
O5—C9—C10	123.29 (17)	N33—C32—H32	116.9
O6—C9—C10	111.96 (14)	N31—C32—H32	116.9
C11—C10—C15	119.17 (17)	N33—C34—N39	127.19 (15)
C11—C10—C9	116.93 (15)	N33—C34—C35	126.78 (15)
C15—C10—C9	123.89 (15)	N39—C34—C35	106.03 (14)
C12—C11—C10	120.59 (17)	C34—C35—N37	110.17 (14)
C12—C11—H11	119.7	C34—C35—C36	117.93 (14)
C10—C11—H11	119.7	N37—C35—C36	131.87 (15)
C13—C12—C11	120.43 (18)	N40—C36—N31	118.94 (15)
C13—C12—H12	119.8	N40—C36—C35	126.68 (15)
C11—C12—H12	119.8	N31—C36—C35	114.37 (14)
C14—C13—C12	119.71 (18)	N37—C38—N39	113.76 (14)
C14—C13—H13	120.1	N37—C38—H38	123.1
C12—C13—H13	120.1	N39—C38—H38	123.1
C13—C14—C15	120.78 (17)	C32—N31—C36	122.81 (14)
C13—C14—H14	119.6	C32—N31—H31	118.6 (16)
C15—C14—H14	119.6	C36—N31—H31	118.6 (16)
C14—C15—C10	119.31 (16)	C32—N33—C34	111.80 (14)
C14—C15—C16	120.66 (15)	C38—N37—C35	103.70 (13)
C10—C15—C16	120.02 (15)	C38—N39—C34	106.35 (14)
O7—C16—O8	123.33 (16)	C38—N39—H39	128.7 (13)
O7—C16—C15	122.49 (15)	C34—N39—H39	124.8 (13)
O8—C16—C15	114.17 (15)	C36—N40—H401	119.7 (14)
C9—O6—H6	114.6 (17)	C36—N40—H402	121.9 (13)
C16—O8—H8	107.1 (16)	H401—N40—H402	118.3 (19)
N23—C22—N21	125.39 (16)	H1W—O1W—H2W	107 (3)
N23—C22—H22	117.3	H3W—O2W—H4W	113.3 (18)
O2—C1—C2—C3	−44.4 (2)	N27—C25—C26—N30	−0.7 (3)
O1—C1—C2—C3	132.26 (17)	C24—C25—C26—N30	179.76 (19)
O2—C1—C2—C2^i	141.4 (2)	N27—C25—C26—N21	178.77 (18)
O1—C1—C2—C2^i	−42.0 (3)	C24—C25—C26—N21	−0.8 (2)
C2^i—C2—C3—C4	0.6 (3)	N23—C22—N21—C26	−0.2 (3)
C1—C2—C3—C4	−173.87 (15)	N30—C26—N21—C22	−179.36 (18)
C2—C3—C4—C4^i	−0.5 (3)	C25—C26—N21—C22	1.1 (3)
O3—C5—C6—C7	−128.20 (18)	N21—C22—N23—C24	−1.0 (3)
O4—C5—C6—C7	48.1 (2)	N29—C24—N23—C22	−178.67 (18)
O3—C5—C6—C6^ii	44.8 (3)	C25—C24—N23—C22	1.4 (3)
O4—C5—C6—C6^ii	−138.92 (19)	N29—C28—N27—C25	0.1 (2)
C6^ii—C6—C7—C8	−2.6 (3)	C24—C25—N27—C28	0.0 (2)
C5—C6—C7—C8	170.45 (15)	C26—C25—N27—C28	−179.6 (2)
C6—C7—C8—C8^ii	−0.3 (3)	N23—C24—N29—C28	−179.82 (19)
O5—C9—C10—C11	85.2 (2)	C25—C24—N29—C28	0.2 (2)
O6—C9—C10—C11	−90.50 (19)	N27—C28—N29—C24	−0.2 (2)
O5—C9—C10—C15	−96.1 (2)	N33—C34—C35—N37	−178.81 (17)
O6—C9—C10—C15	88.17 (19)	N39—C34—C35—N37	0.2 (2)
C15—C10—C11—C12	0.4 (3)	N33—C34—C35—C36	−0.7 (3)
C9—C10—C11—C12	179.12 (17)	N39—C34—C35—C36	178.34 (15)
C10—C11—C12—C13	0.0 (3)	C34—C35—C36—N40	−177.81 (18)
C11—C12—C13—C14	−0.3 (3)	N37—C35—C36—N40	−0.2 (3)
C12—C13—C14—C15	0.2 (3)	C34—C35—C36—N31	1.5 (2)
C13—C14—C15—C10	0.2 (3)	N37—C35—C36—N31	179.13 (18)
C13—C14—C15—C16	179.28 (16)	N33—C32—N31—C36	−0.1 (3)
C11—C10—C15—C14	−0.5 (2)	N40—C36—N31—C32	178.19 (19)
C9—C10—C15—C14	−179.14 (15)	C35—C36—N31—C32	−1.2 (3)
C11—C10—C15—C16	−179.55 (15)	N31—C32—N33—C34	1.0 (3)
C9—C10—C15—C16	1.8 (2)	N39—C34—N33—C32	−179.41 (18)
C14—C15—C16—O7	−159.69 (17)	C35—C34—N33—C32	−0.6 (3)
C10—C15—C16—O7	19.4 (2)	N39—C38—N37—C35	0.3 (2)
C14—C15—C16—O8	19.6 (2)	C34—C35—N37—C38	−0.3 (2)
C10—C15—C16—O8	−161.38 (15)	C36—C35—N37—C38	−178.09 (19)
N29—C24—C25—N27	−0.1 (2)	N37—C38—N39—C34	−0.2 (2)
N23—C24—C25—N27	179.90 (17)	N33—C34—N39—C38	179.01 (18)
N29—C24—C25—C26	179.53 (16)	C35—C34—N39—C38	−0.03 (19)
N23—C24—C25—C26	−0.5 (3)

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O4	0.91 (2)	1.84 (2)	2.7408 (18)	171 (2)
N29—H29···N37	0.92 (2)	1.97 (2)	2.888 (2)	171.1 (19)
N30—H301···O3	0.90 (2)	1.86 (2)	2.757 (2)	172 (2)
N30—H302···N33^iii	0.88 (2)	2.11 (2)	2.971 (2)	168.6 (18)
N31—H31···O1	0.93 (2)	1.67 (2)	2.5930 (19)	174 (2)
N39—H39···O1W	0.91 (2)	1.86 (2)	2.766 (2)	174 (2)
N40—H401···O2	0.87 (2)	2.01 (2)	2.851 (2)	164 (2)
N40—H402···N23	0.95 (2)	2.00 (2)	2.935 (2)	167.5 (19)
O6—H6···O2	0.93 (3)	1.70 (3)	2.6356 (18)	177 (3)
O8—H8···O4	0.88 (3)	1.74 (3)	2.6207 (18)	175 (2)
O1W—H1W···O3^iv	0.86 (3)	1.94 (3)	2.769 (2)	162 (3)
O1W—H2W···O3^v	0.83 (4)	2.24 (4)	3.060 (2)	172 (4)
O2W—H3W···O1^vi	0.89 (1)	2.00 (5)	2.786 (4)	146 (7)
O2W—H4W···O1	0.90 (1)	2.30 (7)	3.074 (6)	145 (10)

Symmetry codes: (iii) x, −y+1, z−1/2; (iv) x, −y+1, z+1/2; (v) −x+2, −y+1, −z+1; (vi) −x+2, y, −z+3/2.