Supramolecular chemistry of amine–phenol adducts; novel three-dimensional framework structures in adducts of bis(2-aminoethyl)amine with 4,4′-sulfonyldiphenol, 1,1,1-tris(4-hydroxyphenyl)­ethane and 3,5-dihydroxybenzoic acid, and in the methanol-solvated adduct of tris(2-aminoethyl)­amine with 4,4′-biphenol

Bis(2-aminoethyl)amine–4,4′-sulfonyldiphenol (1/3) (1) (orthorhombic Pccn with Z′ = 0.5) is a salt, [HN(CH₂CH₂NH₃)₂]²⁺.[O₂S(C₆H₄O)₂]²⁻.[O₂S(C₆H₄OH)₂]₂, containing both dianionic and neutral bis-phenol units. The neutral and anionic bis-phenol units are linked by strong O—H...O⁻ hydrogen bonds to form ladders built from rings: each ladder is interwoven with its two nearest neighbours to form a continuous two-dimensional sheet. The amine cations play two roles: they link each ladder to its two next-nearest neighbours by means of N—H...O hydrogen bonds and they also link each sheet to the two neighbouring sheets, again via N—H...O hydrogen bonds, thus generating a three-dimensional framework. Bis(2-aminoethyl)amine–1,1,1-tris(4-hydroxyphenyl)ethane–methanol (1/4/1) (2) (triclinic P1 with Z′ = 0.5) consists entirely of neutral fragments. The tris-phenol units are linked by O—H...O hydrogen bonds into molecular ladders built from rings: these ladders are linked by the amine units, firstly into sheets and thence into a three-dimensional framework. Bis(2-aminoethyl)amine–3,5-dihydroxybenzoic acid (1/2) (3) (monoclinic P2₁/c with Z′ = 1) is a salt [HN(CH₂CH₂NH₃)₂]²⁺.[{(HO)₂C₆H₃COO}⁻]₂. The 3,5-dihydroxybenzoate anions are linked by O—H...O hydrogen bonds into interwoven and cross-connected (001) sheets linked by further O—H...O hydrogen bonds into a three-dimensional framework. The (001) sheets are further linked by ladders formed from both cations and anions. Tris(2-aminoethyl)amine–4,4′-biphenol–methanol (1/3/1), (4) (monoclinic P2₁), is a salt [{(H₂NCH₂­CH₂)₂­N(CH₂CH₂NH₃)}⁺]₂.[OC₆H₄­C₆H₄O]²⁻.[HOC₆H₄C₆H₄OH]₅.[MeOH]₂, with Z′ = 1. The asymmetric unit, containing ten independent molecular components, can be regarded as a supermolecule held together by a total of 13 independent hydrogen bonds, of O—H...O, O—H...N and N—H...O types. The supermolecules are linked by O—H...O and N—H...O hydrogen bonds into two-dimensional sheets, generated by translation; further N—H...O hydrogen bonds around the 2₁ screw axes link neighbouring sheets together into a three-dimensional framework.

Computing details

Data collection: CAD4 (Enraf-Nonius, 1992) for 9810; CAD-4-PC Software (Enraf-Nonius, 1992) for 9811, 9828; SMART (Siemens, 1996) for 9733frav. Cell refinement: SET4 & CELDIM (Enraf-Nonius, 1992) for 9810, 9811, 9828; SAINT (Siemens, 1996) for 9733frav. Data reduction: DATRD2 in NRCVAX96 (Gabe, Le Page, Charland, Lee & White, 1989) for 9810; DATRD2 in NRCVAX96 (Gabe et al., 1989) for 9811, 9828; SAINT (Siemens, 1996) for 9733frav. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997b). Molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998) for 9810, 9811, 9828; NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1999) for 9733frav. Software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998) for 9810, 9811, 9828; NRCVAX96, SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999) for 9733frav.

(9810) Bis(2-aminoethyl)amine-4,4'-sulfonyldiphenol (1/3)

Crystal data

2(C12H10O4S)·C12H8O4S·C4H15N3	? #Insert any comments here.
Mr = 853.95	Dx = 1.419 Mg m^−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.7107 Å
a = 13.7305 (5) Å	Cell parameters from 25 reflections
b = 14.9948 (6) Å	θ = 10.6–21.4°
c = 19.4209 (9) Å	µ = 0.25 mm^−1
V = 3998.5 (3) Å^3	T = 294 K
Z = 4	Block, yellow
F(000) = 1792	0.41 × 0.41 × 0.40 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.000
Radiation source: X-ray tube	θmax = 27.4°, θmin = 2.0°
Graphite monochromator	h = 0→17
θ/2θ scans	k = 0→19
4595 measured reflections	l = 0→25
4595 independent reflections	3 standard reflections every 240 min
3159 reflections with I > 2σ(I)	intensity decay: no decay, variation 1.0%

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)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0551P)^2 + 0.6244P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4595 reflections	Δρmax = 0.28 e Å^−3
302 parameters	Δρmin = −0.23 e Å^−3
6 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0020 (3)

Special details

Experimental. ? #Insert any special details here.

Geometry. Mean-plane data ex last SHELXL run

Equivalent position $1 is 0.5 - X, 0.5 - Y, Z

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 7.2792 (0.0158) x + 12.7141 (0.0108) y - 0.0000 (0.0000) z = 1.3587 (0.0066)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C11_$1

Rms deviation of fitted atoms = 0.0000

11.7365 (0.0084) x + 7.7822 (0.0151) y - 0.0000 (0.0002) z = 4.8797 (0.0017)

Angle to previous plane (with approximate e.s.d.) = 89.25 (0.08)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) O11 * 0.0000 (0.0000) O11_$1

Rms deviation of fitted atoms = 0.0000

- 7.2792 (0.0158) x + 12.7141 (0.0108) y - 0.0000 (0.0000) z = 1.3587 (0.0066)

Angle to previous plane (with approximate e.s.d.) = 89.25 (0.08)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C11_$1

Rms deviation of fitted atoms = 0.0000

8.5187 (0.0052) x + 1.5229 (0.0119) y + 15.1029 (0.0044) z = 9.4675 (0.0036)

Angle to previous plane (with approximate e.s.d.) = 75.95 (0.06)

* -0.0040 (0.0009) S1 * 0.0000 (0.0014) C11 * 0.0031 (0.0017) C12 * 0.0009 (0.0017) C13 * -0.0030 (0.0015) C14 * -0.0006 (0.0015) C15 * 0.0047 (0.0014) C16 * -0.0011 (0.0011) O14

Rms deviation of fitted atoms = 0.0027

5.2090 (0.0115) x - 8.4432 (0.0199) y + 14.2585 (0.0173) z = 7.3622 (0.0113)

Angle to previous plane (with approximate e.s.d.) = 41.48 (0.08)

* 0.0000 (0.0000) S2 * 0.0000 (0.0000) O21 * 0.0000 (0.0000) O22

Rms deviation of fitted atoms = 0.0000

12.4024 (0.0060) x + 0.4162 (0.0167) y - 8.3155 (0.0181) z = 4.4820 (0.0109)

Angle to previous plane (with approximate e.s.d.) = 89.27 (0.07)

* 0.0000 (0.0000) S2 * 0.0000 (0.0000) C21 * 0.0000 (0.0000) C31

Rms deviation of fitted atoms = 0.0000

10.8496 (0.0062) x + 3.8542 (0.0039) y + 10.8051 (0.0116) z = 10.7187 (0.0010)

Angle to previous plane (with approximate e.s.d.) = 61.14 (0.05)

* 0.0370 (0.0008) S2 * -0.0086 (0.0013) C21 * -0.0183 (0.0014) C22 * -0.0151 (0.0015) C23 * -0.0023 (0.0014) C24 * -0.0163 (0.0013) C25 * -0.0152 (0.0013) C26 * 0.0388 (0.0011) O24

Rms deviation of fitted atoms = 0.0224

12.4024 (0.0060) x + 0.4162 (0.0167) y - 8.3155 (0.0181) z = 4.4820 (0.0109)

Angle to previous plane (with approximate e.s.d.) = 61.14 (0.05)

* 0.0000 (0.0000) S2 * 0.0000 (0.0000) C21 * 0.0000 (0.0000) C31

Rms deviation of fitted atoms = 0.0000

- 3.2327 (0.0094) x + 14.4816 (0.0031) y + 2.1134 (0.0077) z = 0.3563 (0.0050)

Angle to previous plane (with approximate e.s.d.) = 76.56 (0.07)

* -0.0528 (0.0009) S2 * 0.0092 (0.0015) C31 * 0.0259 (0.0014) C32 * 0.0207 (0.0014) C33 * -0.0024 (0.0015) C34 * 0.0207 (0.0014) C35 * 0.0298 (0.0014) C36 * -0.0511 (0.0012) O34

Rms deviation of fitted atoms = 0.0314

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.3048 (3)	0.0557 (2)	0.2986 (2)	0.0481 (10)	0.50
C2	0.2511 (4)	0.1210 (4)	0.2580 (4)	0.069 (2)	0.50
C3	0.3071 (3)	0.2045 (3)	0.2464 (2)	0.0572 (10)	0.50
N4	0.2451 (10)	0.2700 (2)	0.2121 (2)	0.0772 (18)	0.50
C5	0.2894 (4)	0.3585 (3)	0.2100 (2)	0.0680 (12)	0.50
C6	0.2682 (3)	0.4058 (4)	0.2755 (4)	0.0556 (14)	0.50
N7	0.1648 (3)	0.4041 (3)	0.2925 (3)	0.0747 (14)	0.50
S1	0.2500	0.2500	0.46038 (3)	0.05243 (19)
O11	0.29670 (11)	0.17957 (11)	0.42222 (7)	0.0747 (5)
O14	−0.03963 (9)	0.08335 (9)	0.64074 (7)	0.0572 (4)
C11	0.16364 (13)	0.20056 (12)	0.51435 (8)	0.0435 (4)
C12	0.16358 (15)	0.10917 (13)	0.52380 (11)	0.0581 (5)
C13	0.09555 (15)	0.07048 (13)	0.56593 (12)	0.0617 (5)
C14	0.02545 (12)	0.12113 (12)	0.60010 (9)	0.0450 (4)
C15	0.02731 (14)	0.21310 (13)	0.58994 (10)	0.0519 (5)
C16	0.09532 (14)	0.25233 (13)	0.54797 (9)	0.0508 (4)
S2	0.59820 (4)	0.10219 (3)	0.35832 (2)	0.04981 (14)
O21	0.50476 (11)	0.06029 (10)	0.36764 (8)	0.0690 (4)
O22	0.66654 (12)	0.06396 (9)	0.31071 (7)	0.0663 (4)
O24	0.54328 (10)	0.47638 (9)	0.28015 (7)	0.0546 (3)
O34	0.77739 (9)	0.10225 (11)	0.63285 (6)	0.0584 (4)
C21	0.57837 (12)	0.21348 (12)	0.33431 (9)	0.0416 (4)
C22	0.62341 (14)	0.24728 (13)	0.27612 (9)	0.0491 (4)
C23	0.60986 (14)	0.33513 (13)	0.25869 (9)	0.0517 (5)
C24	0.55164 (12)	0.39045 (12)	0.29860 (8)	0.0416 (4)
C25	0.50524 (12)	0.35554 (12)	0.35635 (9)	0.0427 (4)
C26	0.51899 (12)	0.26757 (12)	0.37403 (9)	0.0451 (4)
C31	0.65288 (13)	0.10675 (11)	0.44011 (9)	0.0438 (4)
C32	0.75036 (13)	0.12870 (12)	0.44667 (9)	0.0459 (4)
C33	0.79360 (12)	0.12864 (13)	0.51077 (9)	0.0467 (4)
C34	0.73928 (13)	0.10644 (11)	0.56885 (9)	0.0431 (4)
C35	0.64068 (13)	0.08705 (12)	0.56184 (10)	0.0494 (4)
C36	0.59795 (13)	0.08748 (12)	0.49786 (10)	0.0490 (4)
H1A	0.3532	0.0334	0.2734	0.072*	0.50
H1B	0.2649	0.0119	0.3112	0.072*	0.50
H1C	0.3292	0.0820	0.3359	0.072*	0.50
H2A	0.1908	0.1353	0.2815	0.083*	0.50
H2B	0.2345	0.0949	0.2138	0.083*	0.50
H3A	0.3296	0.2280	0.2901	0.069*	0.50
H3B	0.3637	0.1920	0.2180	0.069*	0.50
H4	0.2330	0.2517	0.1688	0.093*	0.50
H5A	0.2632	0.3921	0.1715	0.082*	0.50
H5B	0.3592	0.3531	0.2037	0.082*	0.50
H6A	0.3048	0.3781	0.3125	0.067*	0.50
H6B	0.2896	0.4672	0.2717	0.067*	0.50
H7A	0.1325	0.4394	0.2637	0.112*	0.50
H7B	0.1564	0.4232	0.3355	0.112*	0.50
H7C	0.1425	0.3485	0.2888	0.112*	0.50
H12	0.2097	0.0740	0.5016	0.070*
H13	0.0962	0.0089	0.5719	0.074*
H15	−0.0185	0.2486	0.6121	0.062*
H16	0.0954	0.3139	0.5421	0.061*
H24	0.5111	0.5032	0.3091	0.082*
H34	0.8370	0.1012	0.6304	0.088*
H22	0.6625	0.2108	0.2491	0.059*
H23	0.6401	0.3579	0.2196	0.062*
H25	0.4650	0.3916	0.3830	0.051*
H26	0.4883	0.2444	0.4128	0.054*
H32	0.7867	0.1435	0.4079	0.055*
H33	0.8591	0.1434	0.5152	0.056*
H35	0.6036	0.0738	0.6006	0.059*
H36	0.5319	0.0748	0.4934	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.047 (2)	0.041 (2)	0.056 (2)	−0.0055 (16)	0.0024 (17)	−0.0009 (19)
C2	0.071 (4)	0.056 (4)	0.080 (5)	−0.011 (3)	−0.023 (4)	0.004 (3)
C3	0.060 (3)	0.064 (3)	0.048 (2)	−0.001 (2)	0.0024 (19)	0.009 (2)
N4	0.092 (4)	0.087 (5)	0.0527 (18)	0.006 (6)	−0.021 (3)	0.003 (2)
C5	0.091 (3)	0.056 (3)	0.057 (3)	0.008 (2)	0.016 (2)	0.012 (2)
C6	0.059 (3)	0.051 (4)	0.057 (3)	−0.004 (2)	0.001 (2)	0.011 (3)
N7	0.077 (3)	0.079 (3)	0.068 (3)	0.028 (3)	0.017 (3)	0.033 (3)
S1	0.0541 (4)	0.0708 (4)	0.0324 (3)	−0.0176 (3)	0.000	0.000
O11	0.0764 (10)	0.0982 (12)	0.0495 (8)	−0.0288 (9)	0.0225 (7)	−0.0296 (8)
O14	0.0418 (7)	0.0679 (9)	0.0619 (8)	0.0074 (6)	0.0107 (6)	0.0201 (7)
C11	0.0412 (9)	0.0550 (10)	0.0343 (8)	−0.0069 (8)	−0.0013 (7)	0.0005 (8)
C12	0.0558 (11)	0.0528 (11)	0.0657 (12)	0.0003 (9)	0.0209 (10)	−0.0067 (10)
C13	0.0618 (12)	0.0444 (10)	0.0790 (14)	0.0031 (9)	0.0242 (11)	0.0037 (10)
C14	0.0361 (8)	0.0539 (11)	0.0449 (9)	0.0046 (8)	−0.0009 (7)	0.0062 (8)
C15	0.0478 (10)	0.0538 (11)	0.0540 (11)	0.0120 (9)	0.0087 (9)	0.0013 (9)
C16	0.0561 (11)	0.0453 (9)	0.0508 (10)	0.0015 (9)	0.0004 (9)	0.0033 (8)
S2	0.0537 (3)	0.0430 (2)	0.0527 (3)	−0.0077 (2)	−0.0051 (2)	−0.0017 (2)
O21	0.0669 (9)	0.0623 (9)	0.0778 (10)	−0.0288 (7)	−0.0152 (8)	0.0061 (7)
O22	0.0861 (10)	0.0532 (8)	0.0598 (9)	0.0091 (8)	0.0020 (8)	−0.0111 (7)
O24	0.0649 (9)	0.0505 (8)	0.0485 (8)	0.0066 (7)	0.0108 (6)	0.0071 (6)
O34	0.0414 (7)	0.0897 (10)	0.0440 (7)	0.0050 (7)	0.0052 (5)	0.0094 (7)
C21	0.0386 (9)	0.0447 (9)	0.0415 (9)	−0.0043 (7)	−0.0057 (7)	−0.0009 (7)
C22	0.0544 (10)	0.0527 (10)	0.0403 (9)	0.0039 (9)	0.0071 (8)	−0.0041 (8)
C23	0.0620 (12)	0.0587 (11)	0.0343 (9)	0.0021 (9)	0.0107 (8)	0.0039 (8)
C24	0.0399 (9)	0.0482 (10)	0.0366 (8)	−0.0010 (7)	−0.0020 (7)	0.0017 (7)
C25	0.0346 (8)	0.0515 (10)	0.0419 (9)	0.0001 (7)	0.0043 (7)	−0.0023 (8)
C26	0.0388 (9)	0.0553 (11)	0.0412 (9)	−0.0065 (8)	0.0064 (7)	0.0049 (8)
C31	0.0436 (9)	0.0364 (8)	0.0512 (10)	−0.0028 (7)	−0.0012 (8)	0.0045 (8)
C32	0.0411 (8)	0.0522 (10)	0.0443 (9)	−0.0014 (8)	0.0065 (8)	0.0083 (8)
C33	0.0336 (8)	0.0547 (10)	0.0518 (10)	−0.0036 (8)	0.0043 (8)	0.0058 (8)
C34	0.0402 (9)	0.0436 (9)	0.0454 (9)	0.0054 (7)	0.0039 (7)	0.0053 (8)
C35	0.0409 (9)	0.0558 (11)	0.0515 (10)	0.0001 (8)	0.0106 (8)	0.0109 (9)
C36	0.0362 (8)	0.0500 (10)	0.0606 (12)	−0.0042 (8)	0.0030 (8)	0.0075 (9)

Geometric parameters (Å, º)

N1—C2	1.457 (4)	C15—C16	1.372 (3)
C2—C3	1.487 (6)	S2—O21	1.4400 (14)
C3—N4	1.460 (8)	S2—O22	1.4367 (15)
N4—C5	1.460 (8)	S2—C21	1.7539 (19)
C5—C6	1.486 (6)	S2—C31	1.7583 (18)
C6—N7	1.457 (4)	O24—C24	1.342 (2)
N1—N7^i	0.743 (5)	O34—C34	1.350 (2)
C2—C6^i	0.589 (6)	C21—C22	1.384 (2)
C3—C5^i	1.774 (7)	C21—C26	1.385 (2)
N4—N4^i	0.614 (7)	C22—C23	1.373 (3)
S1—O11^i	1.4407 (15)	C23—C24	1.388 (2)
S1—O11	1.4407 (15)	C24—C25	1.392 (2)
S1—C11	1.7476 (17)	C25—C26	1.376 (2)
S1—C11^i	1.7476 (17)	C31—C32	1.384 (2)
O14—C14	1.320 (2)	C31—C36	1.382 (2)
C11—C12	1.382 (3)	C32—C33	1.379 (2)
C11—C16	1.382 (3)	C33—C34	1.393 (2)
C12—C13	1.370 (3)	C34—C35	1.391 (2)
C13—C14	1.394 (3)	C35—C36	1.374 (3)
C14—C15	1.393 (3)
N1—C2—C3	112.7 (4)	O21—S2—C21	108.08 (9)
C2—C3—N4	109.5 (6)	O22—S2—C31	108.55 (9)
C3—N4—C5	112.4 (8)	C22—C21—C26	120.22 (17)
N4—C5—C6	109.1 (4)	S2—C21—C22	119.73 (14)
C5—C6—N7	112.1 (5)	S2—C21—C26	120.04 (13)
O11^i—S1—O11	118.08 (14)	C21—C22—C23	119.48 (17)
O11^i—S1—C11	108.51 (9)	C22—C23—C24	120.91 (16)
O11—S1—C11	107.43 (9)	O24—C24—C23	118.28 (15)
O11^i—S1—C11^i	107.43 (9)	O24—C24—C25	122.47 (16)
O11—S1—C11^i	108.51 (9)	C23—C24—C25	119.25 (17)
C11—S1—C11^i	106.31 (11)	C24—C25—C26	119.91 (16)
C12—C11—C16	119.58 (17)	C21—C26—C25	120.22 (16)
S1—C11—C16	120.38 (15)	C32—C31—C36	120.18 (17)
S1—C11—C12	120.04 (14)	S2—C31—C36	119.46 (14)
C11—C12—C13	119.95 (18)	S2—C31—C32	120.35 (14)
C12—C13—C14	121.61 (19)	C31—C32—C33	119.94 (16)
O14—C14—C15	121.46 (16)	C32—C33—C34	120.05 (16)
O14—C14—C13	121.21 (17)	O34—C34—C35	117.22 (16)
C13—C14—C15	117.33 (17)	O34—C34—C33	123.31 (16)
C14—C15—C16	121.40 (17)	C33—C34—C35	119.46 (17)
C11—C16—C15	120.13 (18)	C34—C35—C36	120.20 (16)
O21—S2—O22	119.26 (9)	C31—C36—C35	120.11 (16)
O22—S2—C21	108.06 (8)
N1—C2—C3—N4	−173.8 (6)	C26—C21—C22—C23	0.9 (3)
C2—C3—N4—C5	169.8 (6)	S2—C21—C22—C23	−178.13 (15)
C3—N4—C5—C6	−84.7 (7)	C21—C22—C23—C24	0.0 (3)
N4—C5—C6—N7	−51.0 (7)	C22—C23—C24—O24	178.14 (17)
O11^i—S1—C11—C16	−39.48 (17)	C22—C23—C24—C25	−1.1 (3)
O11—S1—C11—C16	−168.19 (15)	O24—C24—C25—C26	−177.90 (16)
C11^i—S1—C11—C16	75.80 (14)	C23—C24—C25—C26	1.3 (3)
O11^i—S1—C11—C12	140.74 (16)	C24—C25—C26—C21	−0.4 (3)
O11—S1—C11—C12	12.03 (19)	C22—C21—C26—C25	−0.7 (3)
C11^i—S1—C11—C12	−103.98 (17)	S2—C21—C26—C25	178.33 (13)
C16—C11—C12—C13	0.5 (3)	O22—S2—C31—C36	−140.71 (15)
S1—C11—C12—C13	−179.74 (17)	O21—S2—C31—C36	−11.15 (17)
C11—C12—C13—C14	−0.1 (3)	C21—S2—C31—C36	103.61 (15)
C12—C13—C14—O14	−179.80 (19)	O22—S2—C31—C32	38.75 (17)
C12—C13—C14—C15	−0.2 (3)	O21—S2—C31—C32	168.30 (15)
O14—C14—C15—C16	179.64 (17)	C21—S2—C31—C32	−76.93 (16)
C13—C14—C15—C16	0.0 (3)	C36—C31—C32—C33	2.0 (3)
C14—C15—C16—C11	0.4 (3)	S2—C31—C32—C33	−177.42 (14)
C12—C11—C16—C15	−0.6 (3)	C31—C32—C33—C34	0.1 (3)
S1—C11—C16—C15	179.59 (14)	C32—C33—C34—O34	177.85 (18)
O22—S2—C21—C22	2.48 (17)	C32—C33—C34—C35	−1.9 (3)
O21—S2—C21—C22	−127.85 (15)	O34—C34—C35—C36	−178.05 (17)
C31—S2—C21—C22	118.48 (15)	C33—C34—C35—C36	1.7 (3)
O22—S2—C21—C26	−176.59 (14)	C34—C35—C36—C31	0.3 (3)
O21—S2—C21—C26	53.08 (16)	C32—C31—C36—C35	−2.2 (3)
C31—S2—C21—C26	−60.59 (15)	S2—C31—C36—C35	177.23 (15)

Symmetry code: (i) −x+1/2, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O24^ii	0.89	1.96	2.847 (4)	176
N1—H1B···O34^iii	0.89	2.11	2.942 (4)	156
N1—H1C···O11	0.89	2.27	3.037 (4)	144
N1—H1C···O21	0.89	2.51	3.056 (4)	120
N7—H7A···O24^iv	0.89	1.95	2.826 (5)	166
N7—H7B···O11^i	0.89	2.37	2.864 (6)	115
N7—H7B···O21^i	0.89	2.31	2.799 (5)	114
N7—H7C···N4	0.89	2.36	2.774 (8)	108
O24—H24···O14^v	0.82	1.67	2.4958 (19)	164
O34—H34···O14^vi	0.82	1.73	2.5330 (18)	167

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

(9811) Bis(2-aminoethyl)amine–1,1,1-tris(4-hydroxyphenyl)ethane– methanol (1/4/1)

Crystal data

4(C20H18O3)·C4H13N3·CH4O	F(000) = 724
Mr = 1360.59	? #Insert any comments here.
Triclinic, P1	Dx = 1.245 Mg m^−3
a = 10.7171 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2112 (11) Å	Cell parameters from 25 reflections
c = 15.5547 (19) Å	θ = 9.3–19.3°
α = 101.069 (9)°	µ = 0.08 mm^−1
β = 92.924 (9)°	T = 294 K
γ = 97.291 (9)°	Plate, colourless
V = 1813.9 (3) Å^3	0.42 × 0.36 × 0.26 mm
Z = 1

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.000
Radiation source: X-ray tube	θmax = 25.1°, θmin = 2.1°
Graphite monochromator	h = −12→12
θ/2θ scans	k = 0→13
6491 measured reflections	l = −18→18
6491 independent reflections	3 standard reflections every 120 min
4176 reflections with I > 2σ(I)	intensity decay: no decay, variation 0.4%

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)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.164	w = 1/[σ^2(Fo^2) + (0.0829P)^2 + 0.3479P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.007
6491 reflections	Δρmax = 0.46 e Å^−3
495 parameters	Δρmin = −0.36 e Å^−3
17 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (2)

Special details

Experimental. ? #Insert any special details here.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O8	0.1194 (6)	0.6062 (4)	0.6642 (4)	0.0867 (15)	0.50
C9	0.1704 (12)	0.6105 (9)	0.7512 (6)	0.105 (3)	0.50
N1	0.9125 (7)	0.4079 (7)	0.2896 (6)	0.093 (2)	0.50
C2	0.7783 (6)	0.4213 (6)	0.2958 (5)	0.0727 (17)	0.50
C3	0.7458 (4)	0.4372 (4)	0.3908 (3)	0.0546 (11)	0.50
N4	0.6136 (9)	0.4574 (7)	0.3980 (6)	0.0552 (15)	0.50
C5	0.5745 (9)	0.4652 (8)	0.4884 (6)	0.0526 (17)	0.50
C6	0.4398 (9)	0.4928 (8)	0.4935 (6)	0.0526 (17)	0.50
N7	0.3999 (10)	0.5010 (7)	0.5831 (6)	0.0552 (15)	0.50
C11	0.1131 (2)	0.29781 (19)	−0.02624 (13)	0.0430 (5)
C12	0.2283 (2)	0.3478 (2)	−0.05040 (15)	0.0545 (6)
C13	0.3349 (2)	0.3753 (2)	0.00653 (16)	0.0590 (6)
C14	0.3300 (2)	0.3552 (2)	0.09101 (14)	0.0507 (6)
O14	0.44019 (15)	0.38146 (19)	0.14380 (11)	0.0694 (5)
C15	0.2170 (2)	0.3086 (2)	0.11735 (15)	0.0549 (6)
C16	0.1098 (2)	0.2797 (2)	0.05919 (14)	0.0499 (5)
C21	−0.1221 (2)	0.2277 (2)	−0.05111 (14)	0.0479 (5)
C22	−0.1894 (2)	0.3196 (3)	−0.01243 (18)	0.0674 (7)
C23	−0.2966 (3)	0.2966 (4)	0.0281 (2)	0.0824 (9)
C24	−0.3416 (3)	0.1793 (4)	0.0321 (2)	0.0818 (9)
O24	−0.4501 (2)	0.1467 (3)	0.0709 (2)	0.1246 (10)
C25	−0.2790 (3)	0.0829 (3)	−0.0057 (2)	0.0789 (9)
C26	−0.1690 (2)	0.1090 (3)	−0.04661 (16)	0.0607 (7)
C31	0.0219 (2)	0.1469 (2)	−0.16311 (13)	0.0456 (5)
C32	−0.0515 (2)	0.1128 (2)	−0.24231 (15)	0.0539 (6)
C33	−0.0381 (2)	0.0092 (3)	−0.30218 (16)	0.0654 (7)
C34	0.0494 (3)	−0.0634 (3)	−0.28507 (17)	0.0742 (8)
O34	0.0667 (3)	−0.1664 (2)	−0.34510 (16)	0.1186 (10)
C35	0.1233 (3)	−0.0332 (3)	−0.20746 (19)	0.0833 (10)
C36	0.1092 (2)	0.0714 (2)	−0.14760 (16)	0.0635 (7)
C71	−0.0010 (2)	0.2593 (2)	−0.09505 (14)	0.0455 (5)
C72	−0.0144 (3)	0.3670 (2)	−0.14262 (17)	0.0645 (7)
C41	0.4893 (2)	−0.0528 (3)	0.29823 (15)	0.0651 (7)
C42	0.3913 (3)	−0.0194 (3)	0.25005 (19)	0.0787 (9)
C43	0.3781 (3)	0.1004 (3)	0.2502 (2)	0.0794 (9)
C44	0.4632 (2)	0.1936 (3)	0.29955 (16)	0.0666 (8)
O44	0.44549 (18)	0.3129 (2)	0.29876 (13)	0.0782 (6)
C45	0.5623 (3)	0.1642 (3)	0.34770 (17)	0.0764 (9)
C46	0.5750 (3)	0.0425 (3)	0.34637 (17)	0.0752 (9)
C51	0.3770 (2)	−0.2499 (3)	0.32807 (14)	0.0580 (7)
C52	0.3294 (3)	−0.3728 (3)	0.29705 (16)	0.0684 (8)
C53	0.2232 (3)	−0.4280 (3)	0.32789 (17)	0.0665 (7)
C54	0.1613 (2)	−0.3623 (2)	0.39225 (16)	0.0548 (6)
O54	0.05536 (17)	−0.41414 (17)	0.42540 (13)	0.0714 (5)
C55	0.2075 (2)	−0.2406 (2)	0.42512 (16)	0.0582 (6)
C56	0.3124 (2)	−0.1856 (2)	0.39303 (15)	0.0590 (7)
C61	0.6121 (2)	−0.2043 (2)	0.35381 (15)	0.0565 (6)
C62	0.7230 (2)	−0.2327 (2)	0.32009 (15)	0.0538 (6)
C63	0.8241 (2)	−0.2501 (2)	0.37246 (15)	0.0556 (6)
C64	0.8167 (2)	−0.2380 (2)	0.46162 (14)	0.0467 (5)
O64	0.91283 (17)	−0.26131 (18)	0.51478 (12)	0.0715 (5)
C65	0.7099 (2)	−0.2042 (3)	0.49766 (15)	0.0623 (7)
C66	0.6099 (2)	−0.1887 (3)	0.44487 (16)	0.0784 (9)
C81	0.4974 (2)	−0.1887 (3)	0.29538 (15)	0.0648 (7)
C82	0.5102 (3)	−0.2486 (4)	0.19793 (17)	0.0922 (11)
H1A	0.9304	0.3982	0.2337	0.139*	0.50
H1B	0.9285	0.3425	0.3107	0.139*	0.50
H2A	0.7267	0.3491	0.2610	0.087*	0.50
H2B	0.7604	0.4920	0.2724	0.087*	0.50
H3A	0.7594	0.3645	0.4132	0.066*	0.50
H3B	0.8007	0.5067	0.4261	0.066*	0.50
H4A	0.6028	0.5275	0.3802	0.066*	0.50
H5A	0.6305	0.5294	0.5281	0.063*	0.50
H5B	0.5812	0.3881	0.5067	0.063*	0.50
H6A	0.4333	0.5697	0.4750	0.063*	0.50
H6B	0.3840	0.4285	0.4538	0.063*	0.50
H7A	0.3210	0.5177	0.5843	0.083*	0.50
H7B	0.4040	0.4298	0.5997	0.083*	0.50
H12	0.2334	0.3631	−0.1069	0.065*
H13	0.4107	0.4077	−0.0120	0.071*
H14	0.4276	0.3622	0.1912	0.104*
H15	0.2121	0.2963	0.1746	0.066*
H16	0.0341	0.2474	0.0781	0.060*
H22	−0.1596	0.4005	−0.0144	0.081*
H23	−0.3388	0.3607	0.0528	0.099*
H24	−0.4887	0.2058	0.0818	0.187*
H25	−0.3102	0.0023	−0.0036	0.095*
H26	−0.1264	0.0451	−0.0714	0.073*
H32	−0.1113	0.1615	−0.2551	0.065*
H33	−0.0888	−0.0118	−0.3546	0.078*
H34	0.0050	−0.2190	−0.3485	0.178*
H35	0.1825	−0.0828	−0.1952	0.100*
H36	0.1600	0.0916	−0.0952	0.076*
H72A	0.0617	0.3864	−0.1700	0.097*
H72B	−0.0294	0.4376	−0.1007	0.097*
H72C	−0.0840	0.3437	−0.1866	0.097*
H42	0.3325	−0.0809	0.2164	0.094*
H43	0.3113	0.1188	0.2169	0.095*
H44	0.5025	0.3600	0.3295	0.117*
H45	0.6208	0.2263	0.3811	0.092*
H46	0.6429	0.0242	0.3787	0.090*
H52	0.3706	−0.4193	0.2542	0.082*
H53	0.1932	−0.5101	0.3051	0.080*
H54	0.0211	−0.4742	0.3894	0.107*
H55	0.1674	−0.1954	0.4693	0.070*
H56	0.3410	−0.1030	0.4154	0.071*
H62	0.7301	−0.2404	0.2600	0.065*
H63	0.8976	−0.2700	0.3474	0.067*
H64	0.9580	−0.3038	0.4850	0.107*
H65	0.7052	−0.1917	0.5582	0.075*
H66	0.5375	−0.1669	0.4706	0.094*
H82A	0.4379	−0.2387	0.1622	0.138*
H82B	0.5153	−0.3344	0.1934	0.138*
H82C	0.5852	−0.2096	0.1780	0.138*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O8	0.104 (4)	0.067 (3)	0.077 (3)	−0.015 (3)	−0.016 (3)	0.009 (3)
C9	0.136 (9)	0.093 (6)	0.074 (6)	−0.019 (6)	−0.007 (6)	0.018 (4)
N1	0.092 (5)	0.094 (5)	0.109 (7)	0.028 (4)	0.042 (5)	0.042 (5)
C2	0.074 (4)	0.073 (4)	0.077 (4)	0.014 (3)	0.011 (4)	0.023 (4)
C3	0.050 (3)	0.051 (3)	0.064 (3)	0.002 (2)	0.001 (2)	0.016 (2)
N4	0.059 (2)	0.055 (5)	0.049 (4)	0.002 (3)	0.0036 (19)	0.010 (3)
C5	0.056 (2)	0.050 (5)	0.048 (4)	0.000 (3)	−0.005 (2)	0.009 (3)
C6	0.056 (2)	0.050 (5)	0.048 (4)	0.000 (3)	−0.005 (2)	0.009 (3)
N7	0.059 (2)	0.055 (5)	0.049 (4)	0.002 (3)	0.0036 (19)	0.010 (3)
C11	0.0480 (12)	0.0410 (12)	0.0387 (11)	0.0109 (9)	0.0009 (9)	0.0025 (9)
C12	0.0575 (14)	0.0633 (15)	0.0398 (12)	0.0005 (11)	−0.0001 (10)	0.0090 (11)
C13	0.0511 (14)	0.0704 (17)	0.0512 (14)	−0.0019 (12)	0.0032 (11)	0.0087 (12)
C14	0.0471 (13)	0.0565 (14)	0.0437 (12)	0.0112 (10)	−0.0058 (10)	−0.0022 (10)
O14	0.0488 (10)	0.0973 (14)	0.0550 (10)	0.0075 (9)	−0.0090 (8)	0.0031 (10)
C15	0.0540 (14)	0.0732 (17)	0.0392 (12)	0.0179 (12)	−0.0006 (10)	0.0111 (11)
C16	0.0451 (12)	0.0608 (15)	0.0450 (12)	0.0095 (10)	0.0029 (10)	0.0122 (10)
C21	0.0447 (12)	0.0562 (14)	0.0405 (11)	0.0122 (10)	−0.0052 (9)	0.0030 (10)
C22	0.0495 (15)	0.0733 (18)	0.0729 (17)	0.0172 (13)	0.0023 (13)	−0.0064 (14)
C23	0.0583 (18)	0.099 (3)	0.087 (2)	0.0227 (17)	0.0110 (15)	0.0011 (18)
C24	0.0488 (16)	0.138 (3)	0.0654 (18)	0.0267 (19)	0.0104 (13)	0.0268 (19)
O24	0.0702 (15)	0.181 (3)	0.135 (2)	0.0238 (16)	0.0413 (15)	0.050 (2)
C25	0.0699 (19)	0.094 (2)	0.0758 (19)	0.0003 (17)	0.0001 (15)	0.0344 (17)
C26	0.0591 (15)	0.0702 (18)	0.0574 (15)	0.0159 (13)	0.0054 (12)	0.0192 (13)
C31	0.0467 (12)	0.0505 (13)	0.0385 (11)	0.0100 (10)	−0.0018 (9)	0.0056 (9)
C32	0.0493 (13)	0.0664 (16)	0.0453 (12)	0.0194 (11)	−0.0082 (10)	0.0053 (11)
C33	0.0665 (16)	0.0768 (18)	0.0452 (13)	0.0241 (14)	−0.0185 (12)	−0.0096 (12)
C34	0.0849 (19)	0.0738 (18)	0.0545 (15)	0.0328 (15)	−0.0182 (14)	−0.0183 (13)
O34	0.146 (2)	0.1031 (18)	0.0881 (15)	0.0708 (16)	−0.0496 (15)	−0.0452 (14)
C35	0.100 (2)	0.0742 (19)	0.0685 (18)	0.0488 (17)	−0.0341 (16)	−0.0181 (15)
C36	0.0729 (17)	0.0647 (16)	0.0480 (13)	0.0264 (13)	−0.0206 (12)	−0.0049 (12)
C71	0.0498 (12)	0.0454 (13)	0.0412 (11)	0.0124 (10)	−0.0038 (9)	0.0062 (9)
C72	0.0785 (18)	0.0564 (15)	0.0591 (15)	0.0147 (13)	−0.0125 (13)	0.0142 (12)
C41	0.0501 (14)	0.110 (2)	0.0392 (12)	0.0245 (14)	0.0044 (11)	0.0167 (13)
C42	0.0594 (17)	0.109 (3)	0.0709 (18)	0.0052 (16)	−0.0174 (14)	0.0362 (17)
C43	0.0531 (16)	0.119 (3)	0.0736 (19)	0.0071 (16)	−0.0160 (14)	0.0455 (18)
C44	0.0524 (15)	0.109 (2)	0.0447 (13)	0.0202 (15)	0.0040 (11)	0.0258 (14)
O44	0.0684 (13)	0.1064 (17)	0.0614 (12)	0.0165 (11)	−0.0124 (9)	0.0223 (11)
C45	0.0577 (16)	0.116 (3)	0.0538 (15)	0.0281 (16)	−0.0096 (12)	0.0049 (15)
C46	0.0574 (16)	0.121 (3)	0.0494 (15)	0.0404 (17)	−0.0059 (12)	0.0074 (15)
C51	0.0486 (13)	0.0856 (19)	0.0381 (12)	0.0283 (12)	−0.0034 (10)	−0.0019 (12)
C52	0.0707 (18)	0.087 (2)	0.0468 (14)	0.0429 (16)	0.0004 (13)	−0.0076 (13)
C53	0.0689 (17)	0.0659 (17)	0.0589 (15)	0.0267 (14)	−0.0080 (13)	−0.0100 (13)
C54	0.0475 (13)	0.0593 (15)	0.0540 (13)	0.0174 (11)	−0.0122 (11)	0.0001 (12)
O54	0.0575 (11)	0.0623 (12)	0.0851 (13)	0.0031 (9)	−0.0066 (10)	−0.0014 (9)
C55	0.0451 (13)	0.0684 (17)	0.0551 (14)	0.0173 (12)	0.0012 (11)	−0.0082 (12)
C56	0.0474 (14)	0.0713 (17)	0.0506 (14)	0.0146 (12)	−0.0018 (11)	−0.0094 (12)
C61	0.0475 (13)	0.0832 (18)	0.0406 (12)	0.0196 (12)	0.0070 (10)	0.0092 (11)
C62	0.0540 (14)	0.0701 (16)	0.0413 (12)	0.0146 (12)	0.0124 (10)	0.0153 (11)
C63	0.0444 (13)	0.0703 (16)	0.0533 (14)	0.0160 (11)	0.0102 (11)	0.0084 (12)
C64	0.0421 (12)	0.0451 (13)	0.0486 (13)	0.0027 (9)	−0.0021 (10)	0.0024 (10)
O64	0.0633 (11)	0.0799 (13)	0.0635 (11)	0.0252 (9)	−0.0201 (9)	−0.0087 (9)
C65	0.0481 (14)	0.097 (2)	0.0394 (12)	0.0087 (13)	0.0039 (10)	0.0084 (12)
C66	0.0449 (14)	0.149 (3)	0.0409 (13)	0.0297 (16)	0.0077 (11)	0.0075 (15)
C81	0.0517 (14)	0.107 (2)	0.0375 (12)	0.0307 (14)	0.0021 (10)	0.0051 (13)
C82	0.0763 (19)	0.162 (3)	0.0382 (14)	0.046 (2)	0.0028 (13)	0.0007 (17)

Geometric parameters (Å, º)

O8—C9	1.423 (10)	C34—O34	1.378 (3)
N1—C2	1.471 (9)	C35—C36	1.381 (3)
C2—C3	1.518 (7)	C71—C72	1.551 (3)
C3—N4	1.470 (9)	C41—C46	1.385 (4)
N4—C5	1.477 (9)	C41—C42	1.390 (4)
C5—C6	1.517 (5)	C41—C81	1.530 (4)
C6—N7	1.467 (9)	C42—C43	1.368 (4)
C11—C16	1.384 (3)	C43—C44	1.375 (4)
C11—C12	1.390 (3)	C44—O44	1.377 (4)
C11—C71	1.543 (3)	C44—C45	1.379 (4)
C12—C13	1.373 (3)	C45—C46	1.385 (4)
C13—C14	1.378 (3)	C51—C52	1.391 (4)
C14—O14	1.369 (3)	C51—C56	1.392 (3)
C14—C15	1.371 (3)	C51—C81	1.540 (4)
C15—C16	1.389 (3)	C52—C53	1.378 (4)
C21—C26	1.378 (3)	C53—C54	1.376 (3)
C21—C22	1.392 (3)	C54—O54	1.379 (3)
C21—C71	1.531 (3)	C54—C55	1.379 (3)
C22—C23	1.358 (4)	C55—C56	1.377 (4)
C23—C24	1.356 (5)	C61—C62	1.373 (3)
C24—O24	1.378 (4)	C61—C66	1.395 (3)
C24—C25	1.395 (5)	C61—C81	1.539 (3)
C25—C26	1.393 (4)	C62—C63	1.379 (3)
C31—C36	1.381 (3)	C63—C64	1.375 (3)
C31—C32	1.388 (3)	C64—C65	1.364 (3)
C31—C71	1.536 (3)	C64—O64	1.371 (3)
C32—C33	1.370 (3)	C65—C66	1.365 (3)
C33—C34	1.365 (4)	C81—C82	1.556 (3)
C34—C35	1.370 (4)
N1—C2—C3	110.2 (6)	C31—C71—C72	108.75 (19)
N4—C3—C2	110.5 (5)	C11—C71—C72	108.49 (18)
C3—N4—C5	112.7 (9)	C46—C41—C42	116.3 (3)
N4—C5—C6	110.8 (6)	C46—C41—C81	124.1 (2)
N7—C6—C5	111.4 (6)	C42—C41—C81	119.6 (3)
C16—C11—C12	116.7 (2)	C43—C42—C41	122.6 (3)
C16—C11—C71	123.4 (2)	C42—C43—C44	120.2 (3)
C12—C11—C71	119.82 (19)	C43—C44—O44	118.4 (2)
C13—C12—C11	122.1 (2)	C43—C44—C45	119.0 (3)
C12—C13—C14	120.3 (2)	O44—C44—C45	122.7 (3)
O14—C14—C15	123.6 (2)	C44—C45—C46	120.2 (3)
O14—C14—C13	117.5 (2)	C45—C46—C41	121.8 (2)
C15—C14—C13	118.9 (2)	C52—C51—C56	116.4 (3)
C14—C15—C16	120.5 (2)	C52—C51—C81	122.2 (2)
C11—C16—C15	121.4 (2)	C56—C51—C81	121.4 (2)
C26—C21—C22	116.8 (2)	C53—C52—C51	122.0 (2)
C26—C21—C71	122.4 (2)	C54—C53—C52	120.4 (3)
C22—C21—C71	120.8 (2)	C53—C54—O54	122.3 (2)
C23—C22—C21	123.1 (3)	C53—C54—C55	118.8 (3)
C24—C23—C22	119.5 (3)	O54—C54—C55	118.9 (2)
C23—C24—O24	123.8 (3)	C56—C55—C54	120.5 (2)
C23—C24—C25	120.3 (3)	C55—C56—C51	121.9 (3)
O24—C24—C25	115.9 (4)	C62—C61—C66	115.8 (2)
C26—C25—C24	119.1 (3)	C62—C61—C81	122.4 (2)
C21—C26—C25	121.2 (3)	C66—C61—C81	121.8 (2)
C36—C31—C32	116.7 (2)	C61—C62—C63	122.1 (2)
C36—C31—C71	122.83 (19)	C64—C63—C62	120.2 (2)
C32—C31—C71	120.33 (19)	C65—C64—O64	119.3 (2)
C33—C32—C31	121.7 (2)	C65—C64—C63	119.1 (2)
C34—C33—C32	120.2 (2)	O64—C64—C63	121.6 (2)
C33—C34—C35	120.0 (2)	C64—C65—C66	120.0 (2)
C33—C34—O34	121.3 (2)	C65—C66—C61	122.6 (2)
C35—C34—O34	118.7 (2)	C41—C81—C51	110.0 (2)
C34—C35—C36	119.4 (2)	C41—C81—C61	110.8 (2)
C35—C36—C31	122.0 (2)	C51—C81—C61	108.7 (2)
C21—C71—C31	109.33 (18)	C41—C81—C82	106.9 (2)
C21—C71—C11	110.78 (17)	C51—C81—C82	110.1 (2)
C31—C71—C11	109.64 (17)	C61—C81—C82	110.3 (2)
C21—C71—C72	109.83 (19)
N1—C2—C3—N4	176.9 (6)	C16—C11—C71—C72	133.8 (2)
C2—C3—N4—C5	176.1 (6)	C12—C11—C71—C72	−49.7 (3)
C3—N4—C5—C6	177.0 (5)	C46—C41—C42—C43	−0.7 (4)
N4—C5—C6—N7	−179.9 (8)	C81—C41—C42—C43	179.5 (3)
C16—C11—C12—C13	1.6 (3)	C41—C42—C43—C44	−0.2 (5)
C71—C11—C12—C13	−175.2 (2)	C42—C43—C44—O44	−179.2 (3)
C11—C12—C13—C14	−0.8 (4)	C42—C43—C44—C45	0.7 (4)
C12—C13—C14—O14	178.3 (2)	C43—C44—C45—C46	−0.3 (4)
C12—C13—C14—C15	−0.7 (4)	O44—C44—C45—C46	179.6 (3)
O14—C14—C15—C16	−177.5 (2)	C44—C45—C46—C41	−0.7 (4)
C13—C14—C15—C16	1.4 (4)	C42—C41—C46—C45	1.2 (4)
C12—C11—C16—C15	−0.8 (3)	C81—C41—C46—C45	−179.1 (2)
C71—C11—C16—C15	175.8 (2)	C56—C51—C52—C53	0.8 (4)
C14—C15—C16—C11	−0.6 (4)	C81—C51—C52—C53	178.5 (2)
C26—C21—C22—C23	−0.2 (4)	C51—C52—C53—C54	−1.0 (4)
C71—C21—C22—C23	−179.3 (2)	C52—C53—C54—O54	−179.5 (2)
C21—C22—C23—C24	0.3 (5)	C52—C53—C54—C55	0.1 (4)
C22—C23—C24—O24	−179.3 (3)	C53—C54—C55—C56	1.0 (4)
C22—C23—C24—C25	−0.6 (5)	O54—C54—C55—C56	−179.4 (2)
C23—C24—C25—C26	0.8 (4)	C54—C55—C56—C51	−1.2 (4)
O24—C24—C25—C26	179.6 (3)	C52—C51—C56—C55	0.2 (4)
C22—C21—C26—C25	0.4 (4)	C81—C51—C56—C55	−177.5 (2)
C71—C21—C26—C25	179.5 (2)	C66—C61—C62—C63	2.8 (4)
C24—C25—C26—C21	−0.7 (4)	C81—C61—C62—C63	−178.1 (3)
C36—C31—C32—C33	0.0 (4)	C61—C62—C63—C64	−0.6 (4)
C71—C31—C32—C33	−176.3 (2)	C62—C63—C64—C65	−2.5 (4)
C31—C32—C33—C34	−0.3 (4)	C62—C63—C64—O64	176.3 (2)
C32—C33—C34—C35	0.6 (5)	O64—C64—C65—C66	−175.6 (3)
C32—C33—C34—O34	−178.5 (3)	C63—C64—C65—C66	3.2 (4)
C33—C34—C35—C36	−0.7 (5)	C64—C65—C66—C61	−1.0 (5)
O34—C34—C35—C36	178.4 (3)	C62—C61—C66—C65	−2.0 (5)
C34—C35—C36—C31	0.4 (5)	C81—C61—C66—C65	178.9 (3)
C32—C31—C36—C35	−0.1 (4)	C46—C41—C81—C51	120.9 (3)
C71—C31—C36—C35	176.1 (3)	C42—C41—C81—C51	−59.3 (3)
C26—C21—C71—C31	24.6 (3)	C46—C41—C81—C61	0.7 (3)
C22—C21—C71—C31	−156.3 (2)	C42—C41—C81—C61	−179.6 (2)
C26—C21—C71—C11	−96.3 (2)	C46—C41—C81—C82	−119.5 (3)
C22—C21—C71—C11	82.8 (2)	C42—C41—C81—C82	60.2 (3)
C26—C21—C71—C72	143.8 (2)	C52—C51—C81—C41	149.3 (2)
C22—C21—C71—C72	−37.1 (3)	C56—C51—C81—C41	−33.1 (3)
C36—C31—C71—C21	−102.3 (3)	C52—C51—C81—C61	−89.2 (3)
C32—C31—C71—C21	73.8 (3)	C56—C51—C81—C61	88.4 (3)
C36—C31—C71—C11	19.3 (3)	C52—C51—C81—C82	31.7 (3)
C32—C31—C71—C11	−164.6 (2)	C56—C51—C81—C82	−150.7 (2)
C36—C31—C71—C72	137.8 (2)	C62—C61—C81—C41	−100.2 (3)
C32—C31—C71—C72	−46.2 (3)	C66—C61—C81—C41	78.9 (3)
C16—C11—C71—C21	13.2 (3)	C62—C61—C81—C51	138.8 (3)
C12—C11—C71—C21	−170.3 (2)	C66—C61—C81—C51	−42.1 (4)
C16—C11—C71—C31	−107.6 (2)	C62—C61—C81—C82	18.0 (4)
C12—C11—C71—C31	69.0 (3)	C66—C61—C81—C82	−162.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O34^i	0.89	2.15	3.026 (8)	168
O14—H14···O44	0.82	1.87	2.667 (3)	164
O24—H24···O14^ii	0.82	2.26	3.061 (4)	165
O34—H34···O64^iii	0.82	2.24	2.627 (3)	109
O44—H44···N4	0.82	1.69	2.504 (9)	176
O44—H44···N7^iv	0.82	2.00	2.796 (9)	164
O54—H54···N1^v	0.82	2.04	2.840 (9)	166
O54—H54···O8^vi	0.82	2.00	2.765 (6)	156
O64—H64···O54^vii	0.82	1.86	2.677 (3)	173
C45—H45···N4	0.93	2.57	3.198 (9)	126

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

(9828) Bis(2-aminoethyl)amine-3,5-dihydroxybenzoic acid (1/2)

Crystal data

C4H15N3·2(C7H5O4)	? #Insert any comments here.
Mr = 411.41	Dx = 1.379 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.2469 (7) Å	Cell parameters from 25 reflections
b = 10.527 (2) Å	θ = 10.0–15.1°
c = 23.052 (3) Å	µ = 0.11 mm^−1
β = 98.144 (9)°	T = 294 K
V = 1981.0 (5) Å^3	Plate, colourless
Z = 4	0.41 × 0.41 × 0.22 mm
F(000) = 872

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.014
Radiation source: X-ray tube	θmax = 25.2°, θmin = 2.1°
Graphite monochromator	h = −9→9
θ/2θ scans	k = 0→12
3807 measured reflections	l = 0→27
3555 independent reflections	3 standard reflections every 120 min
1536 reflections with I > 2σ(I)	intensity decay: no decay, variation 0.6%

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)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0198P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.83	(Δ/σ)max < 0.001
3555 reflections	Δρmax = 0.28 e Å^−3
269 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0042 (4)

Special details

Experimental. ? #Insert any special details here.

Geometry. Mean-plane data from final SHELXL refinement run:-

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 0.7498(0.0083) x + 8.3053(0.0073) y - 13.5694(0.0230) z = 2.8830(0.0060)

* -0.0005(0.0029) C11 * 0.0135(0.0025) C12 * -0.0089(0.0024) C13 * -0.0077(0.0026) C14 * 0.0178(0.0026) C15 * -0.0126(0.0027) C16 * -0.0015(0.0021) C17 0.3138(0.0040) O11 - 0.3309(0.0042) O12 - 0.0224(0.0044) O13 0.0813(0.0050) O15

Rms deviation of fitted atoms = 0.0107

0.2890(0.0142) x + 6.3450(0.0131) y - 18.3048(0.0219) z = 1.4286(0.0084)

Angle to previous plane (with approximate e.s.d.) = 16.9 (2)

* -0.0010(0.0008) C11 * 0.0036(0.0027) C17 * -0.0013(0.0010) O11 * -0.0013(0.0010) O12

Rms deviation of fitted atoms = 0.0021

7.4222(0.0047) x + 3.1324(0.0117) y - 10.2077(0.0203) z = 0.7364(0.0041)

Angle to previous plane (with approximate e.s.d.) = 62.3 (2)

* 0.0003(0.0030) C21 * -0.0127(0.0026) C22 * -0.0086(0.0025) C23 * 0.0223(0.0026) C24 * 0.0086(0.0025) C25 * -0.0312(0.0027) C26 * 0.0212(0.0021) C27 - 0.4697(0.0039) O21 0.5531(0.0041) O22 - 0.0456(0.0047) O23 0.0047(0.0045) O25

Rms deviation of fitted atoms = 0.0178

- 4.9682(0.0099) x - 6.4852(0.0132) y + 13.5474(0.0319) z = 0.1967(0.0113)

Angle to previous plane (with approximate e.s.d.) = 27.5 (2)

* -0.0003(0.0008) C21 * 0.0010(0.0029) C27 * -0.0004(0.0010) O21 * -0.0004(0.0010) O22

Rms deviation of fitted atoms = 0.0006

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O11	−0.0306 (3)	0.5856 (2)	0.12453 (10)	0.0437 (7)
O12	0.0594 (3)	0.4307 (2)	0.07225 (10)	0.0346 (6)
O13	−0.4668 (3)	0.2424 (2)	−0.03663 (10)	0.0417 (7)
O15	−0.6295 (3)	0.4914 (3)	0.11708 (11)	0.0438 (8)
C11	−0.2280 (4)	0.4454 (3)	0.07282 (15)	0.0251 (8)
C12	−0.2646 (4)	0.3650 (3)	0.02457 (14)	0.0259 (9)
C13	−0.4230 (4)	0.3241 (3)	0.00992 (14)	0.0255 (8)
C14	−0.5478 (4)	0.3630 (3)	0.04053 (14)	0.0310 (9)
C15	−0.5117 (4)	0.4448 (3)	0.08674 (14)	0.0299 (9)
C16	−0.3515 (4)	0.4846 (3)	0.10452 (15)	0.0305 (9)
C17	−0.0542 (4)	0.4907 (4)	0.09100 (14)	0.0282 (9)
O21	0.2617 (3)	0.3125 (2)	0.26003 (9)	0.0374 (7)
O22	0.4824 (3)	0.1924 (2)	0.28350 (9)	0.0383 (7)
O23	0.3522 (3)	−0.1750 (2)	0.13473 (9)	0.0412 (7)
O25	0.0873 (3)	0.1855 (2)	0.04779 (9)	0.0376 (7)
C21	0.3086 (4)	0.1428 (3)	0.19602 (14)	0.0256 (9)
C22	0.3563 (4)	0.0170 (3)	0.19337 (14)	0.0285 (9)
C23	0.3136 (4)	−0.0494 (3)	0.14158 (15)	0.0288 (9)
C24	0.2261 (4)	0.0082 (3)	0.09256 (14)	0.0287 (9)
C25	0.1767 (4)	0.1324 (3)	0.09611 (14)	0.0277 (9)
C26	0.2147 (4)	0.1995 (3)	0.14824 (13)	0.0273 (9)
C27	0.3524 (5)	0.2221 (3)	0.25015 (15)	0.0293 (9)
N1	−0.7850 (3)	−0.0774 (3)	−0.27863 (11)	0.0380 (8)
C2	−0.8502 (5)	−0.1813 (4)	−0.24454 (15)	0.0474 (11)
C3	−0.7809 (5)	−0.1697 (4)	−0.18110 (16)	0.0506 (12)
N4	−0.8333 (4)	−0.0508 (3)	−0.15883 (13)	0.0483 (9)
C5	−0.7592 (5)	−0.0222 (4)	−0.09821 (16)	0.0586 (14)
C6	−0.8209 (5)	0.1057 (4)	−0.08249 (17)	0.0593 (14)
N7	−0.7617 (3)	0.2066 (3)	−0.11871 (11)	0.0365 (8)
H13	−0.3946	0.2420	−0.0577	0.063*
H15	−0.7195	0.4650	0.1023	0.066*
H12	−0.1834	0.3397	0.0028	0.031*
H14	−0.6543	0.3338	0.0298	0.037*
H16	−0.3269	0.5368	0.1371	0.037*
H23	0.4026	−0.2021	0.1654	0.062*
H25	0.0692	0.2603	0.0544	0.056*
H22	0.4159	−0.0222	0.2258	0.034*
H24	0.2011	−0.0368	0.0577	0.034*
H26	0.1773	0.2822	0.1511	0.033*
H1A	−0.7925	−0.0038	−0.2602	0.057*
H1B	−0.8431	−0.0734	−0.3142	0.057*
H1C	−0.6806	−0.0931	−0.2818	0.057*
H2A	−0.8207	−0.2630	−0.2594	0.057*
H2B	−0.9687	−0.1762	−0.2489	0.057*
H3A	−0.8188	−0.2398	−0.1592	0.061*
H3B	−0.6623	−0.1728	−0.1767	0.061*
H4A	−0.9430	−0.0523	−0.1604	0.058*
H4B	−0.8084	0.0123	−0.1824	0.058*	0.00
H5A	−0.6407	−0.0210	−0.0954	0.070*
H5B	−0.7900	−0.0865	−0.0717	0.070*
H6A	−0.9397	0.1053	−0.0884	0.071*
H6B	−0.7838	0.1229	−0.0414	0.071*
H7A	−0.6597	0.2278	−0.1039	0.055*
H7B	−0.8262	0.2744	−0.1188	0.055*
H7C	−0.7634	0.1786	−0.1552	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0259 (16)	0.0452 (17)	0.0575 (18)	0.0015 (14)	−0.0029 (14)	−0.0189 (15)
O12	0.0196 (14)	0.0354 (15)	0.0489 (16)	0.0024 (13)	0.0046 (12)	−0.0026 (14)
O13	0.0332 (17)	0.0533 (17)	0.0393 (16)	−0.0001 (15)	0.0071 (13)	−0.0210 (14)
O15	0.0254 (16)	0.062 (2)	0.0454 (17)	−0.0075 (16)	0.0099 (14)	−0.0221 (15)
C11	0.018 (2)	0.022 (2)	0.034 (2)	0.0036 (17)	−0.0005 (17)	0.0071 (17)
C12	0.023 (2)	0.027 (2)	0.027 (2)	0.0029 (18)	0.0017 (16)	−0.0033 (17)
C13	0.027 (2)	0.0208 (19)	0.0266 (19)	−0.0013 (18)	−0.0028 (16)	−0.0023 (16)
C14	0.021 (2)	0.033 (2)	0.038 (2)	−0.0059 (19)	0.0010 (18)	−0.0029 (18)
C15	0.026 (2)	0.036 (2)	0.029 (2)	0.001 (2)	0.0054 (17)	−0.0020 (18)
C16	0.027 (2)	0.033 (2)	0.030 (2)	−0.001 (2)	0.0011 (17)	−0.0037 (18)
C17	0.021 (2)	0.033 (2)	0.030 (2)	0.0012 (19)	−0.0002 (17)	0.0093 (18)
O21	0.0435 (18)	0.0313 (15)	0.0367 (15)	0.0146 (15)	0.0037 (13)	−0.0066 (13)
O22	0.0397 (16)	0.0363 (15)	0.0352 (14)	0.0090 (15)	−0.0081 (12)	−0.0113 (13)
O23	0.059 (2)	0.0288 (15)	0.0326 (15)	0.0147 (15)	−0.0032 (14)	−0.0032 (13)
O25	0.0437 (17)	0.0375 (15)	0.0291 (14)	0.0120 (16)	−0.0032 (12)	0.0052 (13)
C21	0.028 (2)	0.026 (2)	0.024 (2)	−0.0010 (18)	0.0061 (16)	0.0010 (17)
C22	0.034 (2)	0.027 (2)	0.024 (2)	−0.0008 (19)	0.0055 (17)	0.0015 (17)
C23	0.028 (2)	0.029 (2)	0.030 (2)	0.0022 (19)	0.0083 (17)	−0.0018 (18)
C24	0.032 (2)	0.027 (2)	0.027 (2)	−0.0058 (18)	0.0057 (17)	−0.0069 (18)
C25	0.026 (2)	0.030 (2)	0.025 (2)	−0.0014 (18)	−0.0029 (17)	0.0000 (18)
C26	0.028 (2)	0.023 (2)	0.031 (2)	0.0013 (18)	0.0037 (17)	−0.0019 (17)
C27	0.033 (2)	0.026 (2)	0.029 (2)	−0.0050 (19)	0.0055 (19)	0.0027 (17)
N1	0.0306 (19)	0.040 (2)	0.0429 (19)	0.0018 (17)	0.0040 (15)	−0.0009 (17)
C2	0.049 (3)	0.043 (3)	0.052 (3)	−0.012 (2)	0.011 (2)	0.002 (2)
C3	0.065 (3)	0.039 (3)	0.049 (3)	−0.005 (3)	0.012 (2)	0.010 (2)
N4	0.054 (2)	0.044 (2)	0.048 (2)	−0.006 (2)	0.0124 (18)	−0.0040 (18)
C5	0.077 (4)	0.048 (3)	0.049 (3)	−0.024 (3)	0.003 (3)	0.013 (2)
C6	0.074 (4)	0.060 (3)	0.050 (3)	−0.029 (3)	0.030 (3)	−0.007 (2)
N7	0.0299 (19)	0.040 (2)	0.0380 (18)	−0.0012 (17)	0.0008 (15)	−0.0110 (16)

Geometric parameters (Å, º)

O11—C17	1.261 (4)	O25—C25	1.365 (3)
O12—C17	1.257 (4)	C21—C22	1.386 (4)
O13—C13	1.382 (3)	C21—C26	1.388 (4)
O15—C15	1.366 (4)	C21—C27	1.502 (4)
C11—C12	1.396 (4)	C22—C23	1.385 (4)
C11—C16	1.398 (4)	C23—C24	1.391 (4)
C11—C17	1.512 (4)	C24—C25	1.376 (4)
C12—C13	1.372 (4)	C25—C26	1.390 (4)
C13—C14	1.389 (4)	N1—C2	1.491 (4)
C14—C15	1.369 (4)	C2—C3	1.497 (4)
C15—C16	1.392 (4)	C3—N4	1.442 (4)
O21—C27	1.250 (4)	N4—C5	1.475 (4)
O22—C27	1.268 (4)	C5—C6	1.501 (5)
O23—C23	1.374 (4)	C6—N7	1.477 (4)
C12—C11—C16	120.3 (3)	C23—C22—C21	118.8 (3)
C12—C11—C17	120.1 (3)	O23—C23—C22	123.4 (3)
C16—C11—C17	119.6 (3)	O23—C23—C24	115.4 (3)
C13—C12—C11	118.5 (3)	C22—C23—C24	121.3 (3)
C12—C13—O13	121.4 (3)	C25—C24—C23	119.4 (3)
C12—C13—C14	122.0 (3)	O25—C25—C24	118.1 (3)
O13—C13—C14	116.6 (3)	O25—C25—C26	121.8 (3)
C15—C14—C13	119.1 (3)	C24—C25—C26	120.1 (3)
O15—C15—C14	122.2 (3)	C21—C26—C25	120.0 (3)
O15—C15—C16	117.1 (3)	O21—C27—O22	123.7 (3)
C14—C15—C16	120.8 (3)	O21—C27—C21	119.6 (3)
C15—C16—C11	119.3 (3)	O22—C27—C21	116.7 (3)
O12—C17—O11	123.4 (3)	N1—C2—C3	109.8 (3)
O12—C17—C11	118.0 (3)	N4—C3—C2	109.0 (3)
O11—C17—C11	118.5 (3)	C3—N4—C5	114.2 (3)
C22—C21—C26	120.4 (3)	N4—C5—C6	107.6 (3)
C22—C21—C27	122.1 (3)	N7—C6—C5	111.0 (3)
C26—C21—C27	117.5 (3)
C16—C11—C12—C13	−1.1 (5)	C21—C22—C23—O23	−178.7 (3)
C17—C11—C12—C13	178.9 (3)	C21—C22—C23—C24	0.7 (5)
C11—C12—C13—O13	−178.7 (3)	O23—C23—C24—C25	177.5 (3)
C11—C12—C13—C14	1.8 (5)	C22—C23—C24—C25	−1.9 (5)
C12—C13—C14—C15	0.1 (5)	C23—C24—C25—O25	−178.3 (3)
O13—C13—C14—C15	−179.4 (3)	C23—C24—C25—C26	0.2 (5)
C13—C14—C15—O15	177.0 (3)	C22—C21—C26—C25	−4.0 (5)
C13—C14—C15—C16	−2.6 (5)	C27—C21—C26—C25	177.1 (3)
O15—C15—C16—C11	−176.4 (3)	O25—C25—C26—C21	−178.8 (3)
C14—C15—C16—C11	3.3 (5)	C24—C25—C26—C21	2.7 (5)
C12—C11—C16—C15	−1.3 (5)	C22—C21—C27—O21	−152.5 (3)
C17—C11—C16—C15	178.6 (3)	C26—C21—C27—O21	26.3 (5)
C12—C11—C17—O12	−17.9 (5)	C22—C21—C27—O22	27.7 (5)
C16—C11—C17—O12	162.2 (3)	C26—C21—C27—O22	−153.5 (3)
C12—C11—C17—O11	162.8 (3)	N1—C2—C3—N4	62.5 (4)
C16—C11—C17—O11	−17.1 (5)	C2—C3—N4—C5	−174.1 (3)
C26—C21—C22—C23	2.3 (5)	C3—N4—C5—C6	178.0 (3)
C27—C21—C22—C23	−178.9 (3)	N4—C5—C6—N7	−65.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O21^i	0.89	2.10	2.936 (4)	156
N1—H1B···O11^i	0.89	1.95	2.795 (3)	159
N1—H1C···O22^ii	0.89	1.95	2.790 (4)	158
N7—H7A···O13	0.89	2.06	2.887 (4)	153
N7—H7B···O11^iii	0.89	1.88	2.770 (4)	176
N7—H7C···O21^i	0.89	2.00	2.836 (3)	157
O13—H13···O23^ii	0.82	1.99	2.668 (3)	140
O15—H15···O12^iv	0.82	1.89	2.703 (4)	170
O23—H23···O22^v	0.82	1.79	2.576 (3)	160
O25—H25···O12	0.82	1.84	2.659 (3)	172
C6—H6B···O25^iv	0.97	2.53	3.308 (5)	137
C26—H26···O12	0.93	2.49	3.162 (4)	130

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

(9733frav) Tris(2-aminoethyl)amine-4,4'-biphenol-methanol (1/3/1)

Crystal data

2(C6H19N4)·5(C12H10O2)·C12H8O2·2(CH4O)	F(000) = 1576
Mr = 1473.77	Dx = 1.243 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.0041 (2) Å	Cell parameters from 23654 reflections
b = 41.5502 (7) Å	θ = 1.0–28.2°
c = 10.2715 (1) Å	µ = 0.09 mm^−1
β = 112.746 (1)°	T = 293 K
V = 3937.52 (11) Å^3	Block, colourless
Z = 2	0.20 × 0.20 × 0.15 mm

Data collection

Siemens-CCD diffractometer	6625 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	Rint = 0.040
Graphite monochromator	θmax = 28.2°, θmin = 1.0°
ω scans	h = −12→12
23654 measured reflections	k = 0→54
9156 independent reflections	l = 0→13

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.057	w = 1/[σ^2(Fo^2) + (0.0627P)^2 + 0.8778P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.143	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.18 e Å^−3
9156 reflections	Δρmin = −0.21 e Å^−3
986 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0021 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map

Special details

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 9.8483(0.0031) x + 7.1931(0.0715) y + 4.1984(0.0198) z = 4.1601(0.0150)

* -0.0027 (0.0032) C11 * -0.0007 (0.0037) C12 * 0.0055 (0.0036) C13 * -0.0070 (0.0029) C14 * 0.0038 (0.0031) C15 * 0.0011 (0.0032) C16 - 0.0310 (0.0063) O1 - 0.0337 (0.0063) C24

Rms deviation of fitted atoms = 0.0041

- 9.6698(0.0048) x + 6.7559(0.0688) y + 1.9613(0.0200) z = 2.8235(0.0196)

Angle to previous plane (with approximate e.s.d.) = 13.2 (1)

* -0.0025 (0.0030) C21 * -0.0002 (0.0034) C22 * 0.0013 (0.0032) C23 * 0.0004 (0.0028) C24 * -0.0033 (0.0030) C25 * 0.0043 (0.0031) C26 0.0138 (0.0060) O2 - 0.0172 (0.0062) C14

Rms deviation of fitted atoms = 0.0025

4.7369(0.0200) x + 14.9521(0.0825) y + 5.7349(0.0220) z = 9.6413(0.0281)

Angle to previous plane (with approximate e.s.d.) = 56.1 (2)

* 0.0034 (0.0034) C31 * 0.0027 (0.0041) C32 * -0.0105 (0.0042) C33 * 0.0122 (0.0034) C34 * -0.0064 (0.0040) C35 * -0.0014 (0.0041) C36 0.0214 (0.0062) O3 0.0425 (0.0065) C44

Rms deviation of fitted atoms = 0.0073

4.6730(0.0192) x + 15.4431(0.0782) y + 5.7448(0.0209) z = 9.9380(0.0341)

Angle to previous plane (with approximate e.s.d.) = 0.8 (4)

* -0.0094 (0.0033) C41 * 0.0085 (0.0039) C42 * 0.0038 (0.0040) C43 * -0.0154 (0.0034) C44 * 0.0150 (0.0040) C45 * -0.0025 (0.0040) C46 - 0.0278 (0.0059) O4 - 0.0648 (0.0064) C34

Rms deviation of fitted atoms = 0.0103

- 9.9155(0.0029) x - 3.1051(0.0744) y + 2.8969(0.0225) z = 5.0538(0.0522)

Angle to previous plane (with approximate e.s.d.) = 54.6 (2)

* -0.0036 (0.0033) C51 * 0.0003 (0.0039) C52 * 0.0023 (0.0038) C53 * -0.0016 (0.0031) C54 * -0.0017 (0.0034) C55 * 0.0043 (0.0035) C56 0.0037 (0.0066) O5 0.0247 (0.0064) C64

Rms deviation of fitted atoms = 0.0027

- 9.9331(0.0021) x - 4.9317(0.0730) y + 4.0154(0.0209) z = 4.8632(0.0583)

Angle to previous plane (with approximate e.s.d.) = 7.2 (2)

* 0.0059 (0.0031) C61 * 0.0017 (0.0037) C62 * -0.0070 (0.0037) C63 * 0.0048 (0.0030) C64 * 0.0027 (0.0034) C65 * -0.0081 (0.0035) C66 0.0596 (0.0061) O6 0.0584 (0.0064) C54

Rms deviation of fitted atoms = 0.0055

- 1.5114(0.0206) x - 8.7989(0.0748) y + 9.7465(0.0064) z = 3.0962(0.0562)

Angle to previous plane (with approximate e.s.d.) = 79.5 (2)

* -0.0065 (0.0032) C71 * 0.0025 (0.0033) C72 * 0.0049 (0.0032) C73 * -0.0082 (0.0031) C74 * 0.0045 (0.0036) C75 * 0.0029 (0.0036) C76 - 0.0079 (0.0066) O7 - 0.0697 (0.0069) C84

Rms deviation of fitted atoms = 0.0053

- 4.0122(0.0182) x - 13.0175(0.0689) y + 9.7470(0.0057) z = 0.2469(0.0461)

Angle to previous plane (with approximate e.s.d.) = 16.6 (2)

* -0.0165 (0.0031) C81 * 0.0103 (0.0032) C82 * 0.0056 (0.0032) C83 * -0.0153 (0.0032) C84 * 0.0094 (0.0034) C85 * 0.0065 (0.0033) C86 - 0.0535 (0.0065) O8 - 0.0982 (0.0067) C74

Rms deviation of fitted atoms = 0.0114

- 5.2827(0.0171) x + 30.6662(0.0474) y + 6.0760(0.0141) z = 18.9591(0.0209)

Angle to previous plane (with approximate e.s.d.) = 70.0 (2)

* -0.0099 (0.0031) C91 * 0.0081 (0.0032) C92 * 0.0020 (0.0031) C93 * -0.0103 (0.0029) C94 * 0.0087 (0.0035) C95 * 0.0013 (0.0035) C96 0.0192 (0.0059) O9 - 0.0256 (0.0060) C104

Rms deviation of fitted atoms = 0.0077

- 6.3923(0.0162) x + 28.3196(0.0549) y + 5.9157(0.0148) z = 17.4057(0.0263)

Angle to previous plane (with approximate e.s.d.) = 8.0 (3)

* -0.0002 (0.0031) C101 * 0.0043 (0.0033) C102 * -0.0031 (0.0033) C103 * -0.0022 (0.0031) C104 * 0.0063 (0.0036) C105 * -0.0051 (0.0036) C106 - 0.0221 (0.0060) O10 - 0.0116 (0.0062) C94

Rms deviation of fitted atoms = 0.0041

- 2.8709(0.0205) x - 4.3705(0.0738) y + 10.1591(0.0030) z = 13.8988(0.0221)

Angle to previous plane (with approximate e.s.d.) = 63.2 (2)

* 0.0102 (0.0033) C111 * -0.0009 (0.0035) C112 * -0.0085 (0.0035) C113 * 0.0084 (0.0030) C114 * 0.0008 (0.0033) C115 * -0.0100 (0.0034) C116 0.0363 (0.0066) O11 0.0670 (0.0067) C124

Rms deviation of fitted atoms = 0.0076

- 1.2841(0.0227) x - 3.0639(0.0814) y + 9.8781(0.0065) z = 14.4546(0.0144)

Angle to previous plane (with approximate e.s.d.) = 9.5 (2)

* 0.0114 (0.0035) C121 * -0.0074 (0.0042) C122 * -0.0060 (0.0041) C123 * 0.0156 (0.0033) C124 * -0.0121 (0.0032) C125 * -0.0014 (0.0033) C126 0.0185 (0.0070) O12 0.0425 (0.0071) C114

Rms deviation of fitted atoms = 0.0101

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

	x	y	z	Uiso*/Ueq
N1	0.0279 (4)	0.00022 (8)	0.7058 (3)	0.0535 (8)
N11	0.1619 (4)	0.04716 (9)	0.5602 (4)	0.0636 (9)
N12	0.0407 (5)	0.05512 (9)	0.9008 (4)	0.0684 (10)
N13	−0.2670 (4)	0.01894 (9)	0.5029 (4)	0.0600 (9)
C1A	0.1308 (5)	−0.00833 (11)	0.6410 (5)	0.0626 (11)
C2A	0.2316 (5)	0.01885 (11)	0.6434 (5)	0.0619 (11)
C3A	0.0987 (5)	−0.00054 (12)	0.8603 (5)	0.0635 (11)
C4A	0.0283 (6)	0.02108 (13)	0.9328 (5)	0.0723 (13)
C5A	−0.0974 (5)	−0.02128 (11)	0.6577 (5)	0.0616 (11)
C6A	−0.2057 (5)	−0.01375 (10)	0.5123 (5)	0.0634 (11)
N2	−0.6380 (3)	0.85650 (8)	0.8524 (4)	0.0510 (8)
N21	−0.6586 (4)	0.80779 (10)	0.6273 (4)	0.0682 (10)
N22	−0.7560 (4)	0.80628 (9)	1.0061 (4)	0.0663 (10)
N23	−0.3388 (4)	0.83617 (9)	1.0421 (4)	0.0633 (9)
C1B	−0.7158 (5)	0.86022 (11)	0.6979 (5)	0.0659 (12)
C2B	−0.6492 (5)	0.84236 (13)	0.6120 (5)	0.0700 (12)
C3B	−0.7344 (5)	0.86235 (10)	0.9259 (5)	0.0626 (11)
C4B	−0.8309 (5)	0.83349 (11)	0.9217 (5)	0.0623 (11)
C5B	−0.5127 (5)	0.87777 (11)	0.9008 (6)	0.0692 (13)
C6B	−0.4001 (5)	0.86933 (11)	1.0400 (5)	0.0685 (12)
O1	−0.0947 (4)	0.07435 (7)	0.6341 (3)	0.0644 (8)
O2	0.0129 (4)	0.30467 (7)	0.4607 (3)	0.0645 (8)
C11	−0.0816 (4)	0.10668 (10)	0.6160 (4)	0.0516 (9)
C12	−0.0199 (6)	0.12773 (11)	0.7251 (5)	0.0722 (13)
C13	−0.0076 (6)	0.15998 (11)	0.7003 (5)	0.0698 (13)
C14	−0.0552 (4)	0.17265 (9)	0.5639 (4)	0.0466 (8)
C15	−0.1189 (5)	0.15078 (11)	0.4545 (5)	0.0610 (11)
C16	−0.1311 (5)	0.11845 (11)	0.4808 (5)	0.0632 (11)
C21	−0.0018 (4)	0.27303 (9)	0.4889 (5)	0.0513 (9)
C22	−0.0390 (5)	0.25130 (11)	0.3813 (5)	0.0657 (12)
C23	−0.0568 (5)	0.21922 (11)	0.4053 (4)	0.0631 (11)
C24	−0.0380 (4)	0.20722 (9)	0.5387 (4)	0.0476 (9)
C25	0.0000 (5)	0.23025 (10)	0.6446 (5)	0.0582 (10)
C26	0.0171 (5)	0.26233 (10)	0.6225 (5)	0.0594 (11)
O3	0.1353 (3)	0.34186 (6)	0.6819 (3)	0.0511 (6)
O4	−0.5161 (3)	0.51324 (6)	0.7652 (3)	0.0496 (6)
C31	0.0453 (4)	0.36533 (9)	0.6919 (4)	0.0445 (8)
C32	−0.0368 (5)	0.36124 (11)	0.7702 (6)	0.0754 (15)
C33	−0.1277 (6)	0.38507 (11)	0.7808 (6)	0.0780 (16)
C34	−0.1400 (4)	0.41478 (8)	0.7175 (4)	0.0425 (8)
C35	−0.0581 (6)	0.41819 (11)	0.6377 (6)	0.0717 (14)
C36	0.0322 (6)	0.39458 (11)	0.6255 (6)	0.0766 (15)
C41	−0.4241 (4)	0.49001 (9)	0.7560 (4)	0.0452 (8)
C42	−0.3412 (5)	0.49447 (11)	0.6797 (6)	0.0705 (13)
C43	−0.2500 (6)	0.47051 (11)	0.6691 (6)	0.0740 (14)
C44	−0.2360 (4)	0.44092 (9)	0.7339 (4)	0.0433 (8)
C45	−0.3165 (6)	0.43739 (10)	0.8142 (5)	0.0726 (14)
C46	−0.4097 (6)	0.46058 (12)	0.8246 (6)	0.0752 (15)
O5	−0.3939 (4)	0.54994 (7)	0.9872 (3)	0.0732 (9)
O6	−0.5259 (3)	0.78530 (7)	0.8895 (3)	0.0620 (7)
C51	−0.4095 (4)	0.58244 (10)	0.9660 (4)	0.0537 (10)
C52	−0.3817 (6)	0.60179 (12)	1.0831 (5)	0.0782 (15)
C53	−0.3967 (6)	0.63505 (11)	1.0684 (5)	0.0739 (13)
C54	−0.4391 (4)	0.65018 (9)	0.9380 (4)	0.0465 (8)
C55	−0.4662 (5)	0.62986 (10)	0.8235 (5)	0.0621 (11)
C56	−0.4530 (5)	0.59675 (10)	0.8353 (5)	0.0653 (12)
C61	−0.5012 (4)	0.75285 (9)	0.8973 (4)	0.0488 (9)
C62	−0.5390 (6)	0.73324 (11)	0.7787 (5)	0.0715 (13)
C63	−0.5161 (6)	0.70054 (11)	0.7930 (5)	0.0697 (13)
C64	−0.4569 (4)	0.68566 (9)	0.9243 (4)	0.0473 (9)
C65	−0.4198 (5)	0.70564 (11)	1.0400 (5)	0.0646 (11)
C66	−0.4403 (5)	0.73852 (11)	1.0269 (5)	0.0667 (12)
O7	0.0393 (3)	0.76579 (8)	1.0143 (4)	0.0713 (9)
O8	0.0372 (3)	0.53720 (8)	0.7526 (4)	0.0739 (9)
C71	0.0461 (5)	0.73364 (11)	0.9865 (5)	0.0571 (10)
C72	0.1725 (5)	0.71882 (12)	0.9936 (5)	0.0655 (12)
C73	0.1731 (5)	0.68650 (11)	0.9648 (5)	0.0627 (11)
C74	0.0498 (4)	0.66731 (11)	0.9270 (4)	0.0525 (9)
C75	−0.0748 (5)	0.68300 (12)	0.9231 (6)	0.0694 (13)
C76	−0.0774 (5)	0.71537 (12)	0.9518 (6)	0.0697 (12)
C81	0.0472 (5)	0.56811 (11)	0.8018 (4)	0.0572 (10)
C82	−0.0804 (5)	0.58481 (12)	0.7743 (5)	0.0648 (11)
C83	−0.0792 (5)	0.61633 (11)	0.8164 (5)	0.0622 (11)
C84	0.0502 (4)	0.63284 (11)	0.8896 (4)	0.0535 (9)
C85	0.1770 (5)	0.61499 (12)	0.9205 (6)	0.0704 (12)
C86	0.1761 (5)	0.58348 (12)	0.8777 (5)	0.0668 (12)
O9	0.2761 (3)	0.50093 (7)	0.8353 (3)	0.0603 (7)
O10	0.3438 (3)	0.35431 (7)	1.6140 (3)	0.0629 (8)
C91	0.2905 (4)	0.48082 (9)	0.9445 (4)	0.0482 (9)
C92	0.4136 (4)	0.47882 (11)	1.0646 (5)	0.0591 (11)
C93	0.4200 (4)	0.45827 (10)	1.1728 (5)	0.0575 (10)
C94	0.3038 (4)	0.43918 (9)	1.1661 (4)	0.0465 (8)
C95	0.1790 (5)	0.44230 (11)	1.0450 (5)	0.0640 (12)
C96	0.1720 (5)	0.46232 (13)	0.9367 (5)	0.0714 (13)
C101	0.3289 (4)	0.37458 (9)	1.5044 (4)	0.0497 (9)
C102	0.2100 (5)	0.37429 (11)	1.3781 (5)	0.0626 (11)
C103	0.2025 (5)	0.39488 (11)	1.2702 (5)	0.0640 (12)
C104	0.3117 (4)	0.41688 (9)	1.2830 (4)	0.0448 (8)
C105	0.4284 (5)	0.41684 (12)	1.4108 (5)	0.0677 (12)
C106	0.4372 (5)	0.39590 (13)	1.5186 (5)	0.0735 (13)
O11	0.5664 (3)	0.31267 (7)	1.6663 (4)	0.0703 (9)
O12	0.3808 (4)	0.07904 (8)	1.5392 (4)	0.0770 (9)
C111	0.5330 (5)	0.28061 (10)	1.6405 (4)	0.0535 (10)
C112	0.3930 (5)	0.26881 (11)	1.5947 (5)	0.0633 (12)
C113	0.3676 (5)	0.23649 (12)	1.5729 (5)	0.0672 (12)
C114	0.4781 (4)	0.21414 (10)	1.5962 (4)	0.0483 (9)
C115	0.6165 (4)	0.22684 (11)	1.6400 (5)	0.0615 (11)
C116	0.6456 (5)	0.25915 (11)	1.6611 (5)	0.0658 (12)
C121	0.3991 (5)	0.11176 (11)	1.5510 (5)	0.0605 (11)
C122	0.5331 (6)	0.12433 (12)	1.5704 (7)	0.0829 (16)
C123	0.5578 (5)	0.15692 (12)	1.5839 (7)	0.0805 (15)
C124	0.4502 (4)	0.17880 (10)	1.5789 (4)	0.0506 (9)
C125	0.3155 (4)	0.16538 (11)	1.5544 (5)	0.0609 (11)
C126	0.2905 (4)	0.13292 (12)	1.5422 (5)	0.0618 (11)
O13	−0.1857 (4)	0.80849 (10)	0.8921 (4)	0.0890 (11)
C1	−0.2518 (6)	0.79664 (15)	0.7534 (6)	0.0840 (15)
O14	−0.4093 (5)	0.03723 (10)	0.6722 (5)	0.0936 (11)
C2	−0.3511 (8)	0.0525 (2)	0.7991 (8)	0.119 (2)
H11A	0.1019	0.0559	0.5955	0.095*
H11B	0.1122	0.0413	0.4710	0.095*
H12A	0.0303	0.0674	0.9673	0.103*
H12B	0.1274	0.0587	0.8982	0.103*
H13A	−0.3309	0.0224	0.4154	0.090*
H13B	−0.1960	0.0334	0.5243	0.090*
H13C	−0.3109	0.0207	0.5632	0.090*
H1A1	0.0770	−0.0148	0.5439	0.075*
H1A2	0.1879	−0.0266	0.6908	0.075*
H2A1	0.2832	0.0255	0.7406	0.074*
H2A2	0.3028	0.0108	0.6089	0.074*
H3A1	0.1992	0.0058	0.8879	0.076*
H3A2	0.0975	−0.0225	0.8923	0.076*
H4A1	−0.0733	0.0154	0.9027	0.087*
H4A2	0.0739	0.0178	1.0340	0.087*
H5A1	−0.1452	−0.0201	0.7236	0.074*
H5A2	−0.0637	−0.0432	0.6589	0.074*
H6A1	−0.1593	−0.0156	0.4455	0.076*
H6A2	−0.2837	−0.0294	0.4865	0.076*
H21A	−0.6141	0.7978	0.5787	0.102*
H21B	−0.7513	0.8019	0.5946	0.102*
H22A	−0.7068	0.8127	1.0945	0.099*
H22B	−0.6950	0.7981	0.9708	0.099*
H23A	−0.2743	0.8318	1.1284	0.095*
H23B	−0.2957	0.8353	0.9808	0.095*
H23C	−0.4101	0.8218	1.0182	0.095*
H1B1	−0.7196	0.8829	0.6746	0.079*
H1B2	−0.8148	0.8528	0.6719	0.079*
H2B1	−0.6984	0.8482	0.5134	0.084*
H2B2	−0.5482	0.8485	0.6417	0.084*
H3B1	−0.7954	0.8807	0.8833	0.075*
H3B2	−0.6767	0.8677	1.0235	0.075*
H4B1	−0.9057	0.8404	0.9537	0.075*
H4B2	−0.8787	0.8265	0.8244	0.075*
H5B1	−0.5457	0.8995	0.9057	0.083*
H5B2	−0.4691	0.8777	0.8314	0.083*
H6B1	−0.4416	0.8705	1.1110	0.082*
H6B2	−0.3222	0.8850	1.0644	0.082*
H1	−0.0466	0.0695	0.7163	0.097*
H2	0.0423	0.3149	0.5347	0.097*
H12p	0.0142	0.1202	0.8175	0.087*
H13p	0.0338	0.1737	0.7768	0.084*
H15	−0.1541	0.1581	0.3617	0.073*
H16	−0.1735	0.1045	0.4053	0.076*
H22	−0.0526	0.2582	0.2909	0.079*
H23	−0.0822	0.2050	0.3297	0.076*
H25	0.0146	0.2236	0.7356	0.070*
H26	0.0414	0.2768	0.6971	0.071*
H32	−0.0313	0.3419	0.8176	0.090*
H33	−0.1835	0.3809	0.8333	0.094*
H35	−0.0641	0.4374	0.5896	0.086*
H36	0.0861	0.3985	0.5709	0.092*
H42	−0.3458	0.5140	0.6338	0.085*
H43	−0.1952	0.4746	0.6155	0.089*
H45	−0.3078	0.4183	0.8643	0.087*
H46	−0.4641	0.4565	0.8785	0.090*
H5	−0.4308	0.5406	0.9112	0.110*
H6	−0.5637	0.7907	0.8065	0.093*
H52	−0.3529	0.5925	1.1722	0.094*
H53	−0.3776	0.6476	1.1486	0.089*
H55	−0.4947	0.6390	0.7342	0.075*
H56	−0.4734	0.5842	0.7550	0.078*
H62	−0.5801	0.7423	0.6891	0.086*
H63	−0.5412	0.6880	0.7121	0.084*
H65	−0.3796	0.6967	1.1299	0.078*
H66	−0.4122	0.7512	1.1077	0.080*
H7	0.1126	0.7748	1.0156	0.107*
H8	0.1188	0.5301	0.7698	0.111*
H72	0.2573	0.7307	1.0180	0.079*
H73	0.2596	0.6771	0.9708	0.075*
H75	−0.1597	0.6711	0.9003	0.083*
H76	−0.1631	0.7249	0.9476	0.084*
H82	−0.1686	0.5746	0.7266	0.078*
H83	−0.1669	0.6269	0.7956	0.075*
H85	0.2656	0.6247	0.9719	0.084*
H86	0.2632	0.5725	0.9004	0.080*
H9	0.3532	0.5019	0.8248	0.090*
H10	0.2670	0.3533	1.6249	0.094*
H92	0.4937	0.4914	1.0737	0.071*
H93	0.5053	0.4572	1.2530	0.069*
H95	0.0974	0.4304	1.0371	0.077*
H96	0.0866	0.4635	0.8567	0.086*
H102	0.1342	0.3601	1.3657	0.075*
H103	0.1216	0.3940	1.1859	0.077*
H105	0.5036	0.4313	1.4250	0.081*
H106	0.5187	0.3964	1.6025	0.088*
H11	0.4915	0.3231	1.6462	0.105*
H12	0.3085	0.0740	1.5538	0.116*
H112	0.3159	0.2829	1.5788	0.076*
H113	0.2725	0.2292	1.5412	0.081*
H115	0.6936	0.2128	1.6560	0.074*
H116	0.7402	0.2666	1.6890	0.079*
H122	0.6079	0.1105	1.5745	0.099*
H123	0.6493	0.1647	1.5968	0.097*
H125	0.2390	0.1790	1.5459	0.073*
H126	0.1987	0.1251	1.5277	0.074*
H13	−0.1388	0.7941	0.9444	0.133*
H1A	−0.2357	0.7739	0.7532	0.126*
H1B	−0.2108	0.8072	0.6943	0.126*
H1C	−0.3541	0.8008	0.7182	0.126*
H14	−0.4739	0.0484	0.6166	0.140*
H2A	−0.2781	0.0391	0.8653	0.178*
H2B	−0.4259	0.0568	0.8336	0.178*
H2C	−0.3082	0.0725	0.7879	0.178*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0528 (19)	0.058 (2)	0.0498 (19)	−0.0096 (15)	0.0197 (16)	0.0012 (15)
N11	0.060 (2)	0.072 (2)	0.060 (2)	−0.0121 (18)	0.0241 (18)	−0.0043 (18)
N12	0.084 (3)	0.073 (3)	0.053 (2)	−0.012 (2)	0.031 (2)	−0.0101 (18)
N13	0.057 (2)	0.066 (2)	0.049 (2)	−0.0130 (17)	0.0128 (16)	−0.0001 (16)
C1A	0.063 (3)	0.058 (2)	0.071 (3)	−0.005 (2)	0.031 (2)	−0.007 (2)
C2A	0.062 (3)	0.065 (3)	0.063 (3)	−0.008 (2)	0.028 (2)	−0.003 (2)
C3A	0.059 (2)	0.070 (3)	0.051 (2)	−0.006 (2)	0.009 (2)	0.007 (2)
C4A	0.083 (3)	0.091 (4)	0.049 (2)	−0.005 (3)	0.031 (2)	0.000 (2)
C5A	0.060 (3)	0.061 (3)	0.060 (3)	−0.013 (2)	0.020 (2)	0.004 (2)
C6A	0.061 (3)	0.058 (3)	0.068 (3)	−0.012 (2)	0.021 (2)	−0.005 (2)
N2	0.0498 (18)	0.0486 (18)	0.056 (2)	−0.0038 (14)	0.0219 (16)	−0.0003 (15)
N21	0.062 (2)	0.084 (3)	0.057 (2)	−0.0081 (19)	0.0220 (18)	−0.0085 (19)
N22	0.060 (2)	0.070 (2)	0.072 (2)	−0.0110 (18)	0.0303 (19)	−0.0018 (19)
N23	0.0478 (19)	0.078 (3)	0.057 (2)	−0.0085 (17)	0.0129 (16)	−0.0098 (18)
C1B	0.063 (3)	0.065 (3)	0.062 (3)	0.006 (2)	0.016 (2)	0.011 (2)
C2B	0.068 (3)	0.090 (4)	0.049 (3)	−0.003 (2)	0.020 (2)	0.013 (2)
C3B	0.065 (3)	0.049 (2)	0.079 (3)	−0.003 (2)	0.035 (2)	−0.013 (2)
C4B	0.059 (2)	0.066 (3)	0.073 (3)	−0.008 (2)	0.037 (2)	−0.005 (2)
C5B	0.061 (3)	0.058 (3)	0.086 (3)	−0.015 (2)	0.026 (3)	0.003 (2)
C6B	0.067 (3)	0.065 (3)	0.061 (3)	−0.014 (2)	0.012 (2)	−0.010 (2)
O1	0.080 (2)	0.0555 (17)	0.0525 (17)	−0.0188 (15)	0.0198 (16)	−0.0065 (13)
O2	0.073 (2)	0.0534 (17)	0.0581 (18)	0.0045 (14)	0.0160 (16)	0.0015 (14)
C11	0.048 (2)	0.050 (2)	0.055 (2)	−0.0082 (17)	0.0187 (18)	−0.0065 (18)
C12	0.095 (4)	0.061 (3)	0.045 (2)	−0.009 (2)	0.010 (2)	−0.004 (2)
C13	0.093 (3)	0.055 (3)	0.048 (3)	−0.009 (2)	0.011 (2)	−0.0104 (19)
C14	0.0368 (17)	0.052 (2)	0.052 (2)	−0.0033 (15)	0.0180 (16)	−0.0095 (17)
C15	0.067 (3)	0.063 (3)	0.050 (2)	−0.012 (2)	0.020 (2)	−0.008 (2)
C16	0.069 (3)	0.064 (3)	0.055 (3)	−0.018 (2)	0.022 (2)	−0.021 (2)
C21	0.046 (2)	0.048 (2)	0.056 (2)	0.0058 (17)	0.0166 (18)	0.0023 (18)
C22	0.077 (3)	0.062 (3)	0.047 (2)	0.004 (2)	0.012 (2)	0.000 (2)
C23	0.074 (3)	0.060 (3)	0.045 (2)	−0.001 (2)	0.012 (2)	−0.0091 (19)
C24	0.0379 (18)	0.056 (2)	0.047 (2)	0.0036 (16)	0.0145 (16)	−0.0031 (17)
C25	0.069 (3)	0.060 (3)	0.050 (2)	−0.002 (2)	0.027 (2)	−0.0044 (19)
C26	0.065 (3)	0.054 (2)	0.062 (3)	−0.004 (2)	0.026 (2)	−0.011 (2)
O3	0.0509 (15)	0.0453 (14)	0.0586 (16)	0.0081 (12)	0.0228 (13)	0.0024 (12)
O4	0.0496 (15)	0.0433 (14)	0.0542 (16)	0.0062 (11)	0.0184 (12)	0.0029 (12)
C31	0.0391 (18)	0.0410 (19)	0.047 (2)	0.0029 (15)	0.0098 (16)	0.0023 (16)
C32	0.079 (3)	0.055 (3)	0.118 (4)	0.022 (2)	0.066 (3)	0.040 (3)
C33	0.079 (3)	0.067 (3)	0.121 (4)	0.025 (2)	0.074 (3)	0.039 (3)
C34	0.0386 (18)	0.0377 (18)	0.047 (2)	0.0025 (14)	0.0124 (16)	0.0009 (15)
C35	0.100 (4)	0.050 (2)	0.093 (4)	0.024 (2)	0.068 (3)	0.027 (2)
C36	0.112 (4)	0.058 (3)	0.097 (4)	0.021 (3)	0.080 (3)	0.021 (3)
C41	0.0421 (19)	0.0421 (19)	0.046 (2)	−0.0003 (16)	0.0109 (16)	−0.0019 (16)
C42	0.078 (3)	0.048 (2)	0.105 (4)	0.016 (2)	0.057 (3)	0.028 (2)
C43	0.079 (3)	0.056 (3)	0.115 (4)	0.018 (2)	0.068 (3)	0.029 (3)
C44	0.0399 (18)	0.045 (2)	0.042 (2)	0.0009 (15)	0.0122 (15)	0.0025 (16)
C45	0.114 (4)	0.044 (2)	0.085 (3)	0.026 (2)	0.067 (3)	0.023 (2)
C46	0.103 (4)	0.060 (3)	0.090 (4)	0.023 (3)	0.068 (3)	0.022 (3)
O5	0.091 (2)	0.0529 (18)	0.0575 (19)	0.0088 (16)	0.0082 (17)	0.0012 (14)
O6	0.0673 (19)	0.0499 (16)	0.0635 (19)	0.0000 (13)	0.0196 (16)	−0.0073 (13)
C51	0.046 (2)	0.053 (2)	0.055 (2)	0.0037 (18)	0.0120 (18)	−0.0005 (19)
C52	0.110 (4)	0.060 (3)	0.049 (3)	0.005 (3)	0.013 (3)	0.005 (2)
C53	0.097 (4)	0.056 (3)	0.055 (3)	0.001 (2)	0.015 (3)	−0.010 (2)
C54	0.0398 (18)	0.048 (2)	0.051 (2)	−0.0026 (16)	0.0165 (16)	−0.0053 (17)
C55	0.078 (3)	0.055 (2)	0.048 (2)	0.004 (2)	0.018 (2)	0.0009 (19)
C56	0.078 (3)	0.053 (2)	0.056 (3)	0.005 (2)	0.016 (2)	−0.011 (2)
C61	0.044 (2)	0.048 (2)	0.057 (2)	−0.0047 (17)	0.0225 (18)	−0.0054 (18)
C62	0.098 (4)	0.054 (3)	0.050 (3)	0.004 (2)	0.015 (2)	−0.002 (2)
C63	0.095 (3)	0.052 (2)	0.052 (3)	0.001 (2)	0.018 (2)	−0.012 (2)
C64	0.0383 (18)	0.054 (2)	0.050 (2)	−0.0027 (16)	0.0166 (16)	−0.0052 (17)
C65	0.080 (3)	0.060 (3)	0.050 (2)	0.003 (2)	0.022 (2)	−0.004 (2)
C66	0.084 (3)	0.059 (3)	0.050 (3)	0.002 (2)	0.018 (2)	−0.014 (2)
O7	0.0575 (19)	0.069 (2)	0.090 (2)	−0.0076 (15)	0.0321 (18)	0.0051 (18)
O8	0.0629 (19)	0.072 (2)	0.072 (2)	0.0123 (16)	0.0100 (17)	0.0018 (17)
C71	0.059 (2)	0.060 (3)	0.057 (2)	−0.011 (2)	0.027 (2)	0.0030 (19)
C72	0.046 (2)	0.081 (3)	0.067 (3)	−0.015 (2)	0.019 (2)	−0.002 (2)
C73	0.047 (2)	0.077 (3)	0.065 (3)	0.000 (2)	0.023 (2)	0.004 (2)
C74	0.045 (2)	0.065 (2)	0.048 (2)	−0.0057 (18)	0.0187 (17)	0.0061 (18)
C75	0.046 (2)	0.070 (3)	0.095 (4)	−0.010 (2)	0.030 (2)	0.001 (3)
C76	0.051 (2)	0.071 (3)	0.092 (4)	−0.002 (2)	0.033 (2)	0.006 (3)
C81	0.054 (2)	0.069 (3)	0.047 (2)	0.011 (2)	0.0171 (19)	0.013 (2)
C82	0.049 (2)	0.077 (3)	0.059 (3)	0.002 (2)	0.0113 (19)	0.001 (2)
C83	0.048 (2)	0.073 (3)	0.060 (3)	0.007 (2)	0.015 (2)	0.006 (2)
C84	0.045 (2)	0.067 (3)	0.048 (2)	0.0008 (18)	0.0181 (18)	0.0087 (19)
C85	0.047 (2)	0.080 (3)	0.081 (3)	−0.005 (2)	0.022 (2)	−0.004 (3)
C86	0.048 (2)	0.081 (3)	0.070 (3)	0.010 (2)	0.020 (2)	0.011 (2)
O9	0.0526 (16)	0.0689 (18)	0.0649 (18)	0.0111 (14)	0.0288 (15)	0.0137 (15)
O10	0.0563 (17)	0.0666 (18)	0.070 (2)	0.0113 (14)	0.0295 (15)	0.0190 (15)
C91	0.050 (2)	0.049 (2)	0.049 (2)	0.0082 (17)	0.0229 (18)	0.0014 (17)
C92	0.047 (2)	0.065 (3)	0.065 (3)	−0.0088 (19)	0.021 (2)	0.005 (2)
C93	0.045 (2)	0.061 (2)	0.056 (3)	−0.0034 (18)	0.0080 (19)	0.006 (2)
C94	0.045 (2)	0.0435 (19)	0.052 (2)	0.0022 (16)	0.0203 (17)	−0.0086 (17)
C95	0.047 (2)	0.080 (3)	0.059 (3)	−0.018 (2)	0.014 (2)	0.002 (2)
C96	0.051 (2)	0.091 (3)	0.057 (3)	−0.008 (2)	0.004 (2)	0.011 (2)
C101	0.050 (2)	0.047 (2)	0.058 (2)	0.0087 (17)	0.0277 (19)	0.0029 (18)
C102	0.053 (2)	0.059 (3)	0.073 (3)	−0.0122 (19)	0.021 (2)	0.006 (2)
C103	0.052 (2)	0.071 (3)	0.060 (3)	−0.012 (2)	0.012 (2)	0.005 (2)
C104	0.0428 (19)	0.0429 (19)	0.051 (2)	0.0019 (15)	0.0207 (16)	−0.0065 (16)
C105	0.062 (3)	0.070 (3)	0.062 (3)	−0.022 (2)	0.012 (2)	0.006 (2)
C106	0.059 (3)	0.088 (3)	0.060 (3)	−0.015 (2)	0.008 (2)	0.010 (2)
O11	0.0570 (17)	0.0613 (19)	0.088 (2)	0.0069 (15)	0.0228 (17)	0.0152 (17)
O12	0.068 (2)	0.067 (2)	0.106 (3)	−0.0103 (16)	0.044 (2)	−0.0078 (19)
C111	0.054 (2)	0.055 (2)	0.053 (2)	0.0044 (18)	0.0222 (19)	0.0117 (18)
C112	0.042 (2)	0.065 (3)	0.082 (3)	0.0093 (19)	0.023 (2)	0.013 (2)
C113	0.038 (2)	0.072 (3)	0.090 (3)	0.0018 (19)	0.022 (2)	0.002 (2)
C114	0.0369 (18)	0.062 (2)	0.046 (2)	0.0008 (16)	0.0155 (16)	0.0080 (17)
C115	0.042 (2)	0.063 (3)	0.074 (3)	0.0068 (19)	0.016 (2)	0.008 (2)
C116	0.039 (2)	0.066 (3)	0.084 (3)	0.0018 (19)	0.016 (2)	0.004 (2)
C121	0.057 (2)	0.069 (3)	0.066 (3)	−0.011 (2)	0.035 (2)	−0.001 (2)
C122	0.064 (3)	0.063 (3)	0.142 (5)	0.002 (2)	0.063 (3)	0.002 (3)
C123	0.047 (2)	0.075 (3)	0.132 (5)	−0.006 (2)	0.048 (3)	0.003 (3)
C124	0.0411 (19)	0.064 (2)	0.051 (2)	−0.0023 (17)	0.0226 (17)	0.0007 (18)
C125	0.041 (2)	0.072 (3)	0.068 (3)	0.0023 (19)	0.0196 (19)	−0.001 (2)
C126	0.044 (2)	0.076 (3)	0.065 (3)	−0.009 (2)	0.021 (2)	−0.005 (2)
O13	0.074 (2)	0.105 (3)	0.090 (3)	0.008 (2)	0.033 (2)	−0.011 (2)
C1	0.072 (3)	0.105 (4)	0.079 (4)	−0.001 (3)	0.034 (3)	−0.006 (3)
O14	0.086 (3)	0.101 (3)	0.099 (3)	0.007 (2)	0.041 (2)	−0.016 (2)
C2	0.092 (5)	0.162 (7)	0.092 (5)	0.011 (5)	0.025 (4)	0.012 (5)

Geometric parameters (Å, º)

N1—C5A	1.460 (5)	C54—C64	1.485 (5)
N1—C3A	1.467 (5)	C55—C56	1.383 (6)
N1—C1A	1.469 (5)	C61—C66	1.367 (6)
N11—C2A	1.463 (6)	C61—C62	1.391 (6)
N12—C4A	1.468 (6)	C62—C63	1.376 (6)
N13—C6A	1.478 (6)	C63—C64	1.391 (6)
C1A—C2A	1.508 (6)	C64—C65	1.378 (6)
C3A—C4A	1.504 (7)	C65—C66	1.380 (6)
C5A—C6A	1.500 (6)	O7—C71	1.373 (5)
N2—C5B	1.455 (5)	O8—C81	1.370 (6)
N2—C3B	1.457 (6)	C71—C76	1.375 (6)
N2—C1B	1.480 (6)	C71—C72	1.382 (6)
N21—C2B	1.452 (6)	C72—C73	1.376 (7)
N22—C4B	1.445 (6)	C73—C74	1.392 (6)
N23—C6B	1.505 (6)	C74—C75	1.393 (6)
C1B—C2B	1.493 (7)	C74—C84	1.483 (6)
C3B—C4B	1.530 (6)	C75—C76	1.379 (7)
C5B—C6B	1.480 (7)	C81—C86	1.379 (6)
O1—C11	1.369 (5)	C81—C82	1.383 (6)
O2—C21	1.366 (5)	C82—C83	1.378 (7)
C11—C12	1.366 (6)	C83—C84	1.400 (6)
C11—C16	1.372 (6)	C84—C85	1.396 (6)
C12—C13	1.378 (7)	C85—C86	1.380 (7)
C13—C14	1.396 (6)	O9—C91	1.360 (5)
C14—C15	1.394 (5)	O10—C101	1.367 (5)
C14—C24	1.481 (5)	C91—C92	1.368 (6)
C15—C16	1.385 (6)	C91—C96	1.389 (6)
C21—C22	1.363 (6)	C92—C93	1.383 (6)
C21—C26	1.384 (6)	C93—C94	1.387 (6)
C22—C23	1.379 (6)	C94—C95	1.386 (6)
C23—C24	1.402 (6)	C94—C104	1.495 (5)
C24—C25	1.387 (5)	C95—C96	1.369 (6)
C25—C26	1.374 (6)	C101—C106	1.363 (6)
O3—C31	1.357 (4)	C101—C102	1.380 (6)
O4—C41	1.362 (4)	C102—C103	1.379 (6)
C31—C32	1.365 (6)	C103—C104	1.391 (6)
C31—C36	1.375 (6)	C104—C105	1.378 (6)
C32—C33	1.376 (6)	C105—C106	1.384 (7)
C33—C34	1.379 (6)	O11—C111	1.374 (5)
C34—C35	1.371 (6)	O12—C121	1.371 (5)
C34—C44	1.502 (5)	C111—C112	1.384 (6)
C35—C36	1.372 (6)	C111—C116	1.387 (6)
C41—C42	1.356 (6)	C112—C113	1.369 (7)
C41—C46	1.390 (6)	C113—C114	1.391 (6)
C42—C43	1.383 (6)	C114—C115	1.384 (6)
C43—C44	1.379 (6)	C114—C124	1.493 (6)
C44—C45	1.365 (6)	C115—C116	1.373 (6)
C45—C46	1.373 (6)	C121—C126	1.373 (6)
O5—C51	1.367 (5)	C121—C122	1.379 (6)
O6—C61	1.367 (5)	C122—C123	1.374 (7)
C51—C56	1.377 (6)	C123—C124	1.395 (6)
C51—C52	1.382 (6)	C124—C125	1.388 (6)
C52—C53	1.392 (7)	C125—C126	1.368 (6)
C53—C54	1.388 (6)	O13—C1	1.407 (6)
C54—C55	1.387 (6)	O14—C2	1.363 (8)
C5A—N1—C3A	110.2 (3)	O6—C61—C62	123.0 (4)
C5A—N1—C1A	111.0 (3)	C66—C61—C62	117.7 (4)
C3A—N1—C1A	110.8 (4)	C63—C62—C61	120.5 (4)
N1—C1A—C2A	113.2 (4)	C62—C63—C64	122.2 (4)
N11—C2A—C1A	115.4 (4)	C65—C64—C63	116.1 (4)
N1—C3A—C4A	113.6 (4)	C65—C64—C54	122.2 (4)
N12—C4A—C3A	111.6 (4)	C63—C64—C54	121.6 (3)
N1—C5A—C6A	113.8 (4)	C64—C65—C66	122.1 (4)
N13—C6A—C5A	112.3 (4)	C61—C66—C65	121.3 (4)
C5B—N2—C3B	112.1 (4)	O7—C71—C76	118.6 (4)
C5B—N2—C1B	109.3 (3)	O7—C71—C72	122.7 (4)
C3B—N2—C1B	111.0 (3)	C76—C71—C72	118.7 (4)
N2—C1B—C2B	114.3 (4)	C73—C72—C71	120.2 (4)
N21—C2B—C1B	111.4 (4)	C72—C73—C74	122.8 (4)
N2—C3B—C4B	113.1 (3)	C73—C74—C75	115.2 (4)
N22—C4B—C3B	114.9 (4)	C73—C74—C84	122.3 (4)
N2—C5B—C6B	114.8 (4)	C75—C74—C84	122.4 (4)
C5B—C6B—N23	112.6 (4)	C76—C75—C74	122.7 (4)
C12—C11—O1	123.6 (4)	C71—C76—C75	120.3 (4)
C12—C11—C16	118.3 (4)	O8—C81—C86	124.2 (4)
O1—C11—C16	118.1 (4)	O8—C81—C82	117.7 (4)
C11—C12—C13	121.0 (4)	C86—C81—C82	118.1 (4)
C12—C13—C14	122.1 (4)	C83—C82—C81	121.2 (4)
C15—C14—C13	115.8 (4)	C82—C83—C84	121.9 (4)
C15—C14—C24	122.6 (4)	C85—C84—C83	115.6 (4)
C13—C14—C24	121.6 (3)	C85—C84—C74	123.2 (4)
C16—C15—C14	121.5 (4)	C83—C84—C74	121.2 (4)
C11—C16—C15	121.2 (4)	C86—C85—C84	122.5 (4)
C22—C21—O2	119.0 (4)	C81—C86—C85	120.6 (4)
C22—C21—C26	118.7 (4)	O9—C91—C92	123.5 (4)
O2—C21—C26	122.3 (4)	O9—C91—C96	118.5 (4)
C21—C22—C23	120.7 (4)	C92—C91—C96	118.0 (4)
C22—C23—C24	122.7 (4)	C91—C92—C93	120.5 (4)
C25—C24—C23	114.5 (4)	C92—C93—C94	122.4 (4)
C25—C24—C14	123.2 (4)	C95—C94—C93	116.0 (4)
C23—C24—C14	122.4 (3)	C95—C94—C104	121.9 (3)
C26—C25—C24	123.6 (4)	C93—C94—C104	122.1 (3)
C25—C26—C21	119.8 (4)	C96—C95—C94	122.1 (4)
O3—C31—C32	121.5 (3)	C95—C96—C91	121.0 (4)
O3—C31—C36	122.5 (4)	C106—C101—O10	118.9 (4)
C32—C31—C36	116.0 (4)	C106—C101—C102	117.8 (4)
C31—C32—C33	121.6 (4)	O10—C101—C102	123.3 (4)
C32—C33—C34	123.2 (4)	C103—C102—C101	120.6 (4)
C35—C34—C33	114.2 (3)	C102—C103—C104	122.3 (4)
C35—C34—C44	123.2 (3)	C105—C104—C103	115.7 (4)
C33—C34—C44	122.6 (3)	C105—C104—C94	121.9 (3)
C34—C35—C36	123.2 (4)	C103—C104—C94	122.4 (3)
C35—C36—C31	121.8 (4)	C104—C105—C106	122.1 (4)
C42—C41—O4	121.6 (4)	C101—C106—C105	121.4 (4)
C42—C41—C46	116.5 (4)	O11—C111—C112	123.2 (4)
O4—C41—C46	121.9 (4)	O11—C111—C116	118.1 (4)
C41—C42—C43	121.1 (4)	C112—C111—C116	118.7 (4)
C44—C43—C42	123.4 (4)	C113—C112—C111	120.1 (4)
C45—C44—C43	114.5 (4)	C112—C113—C114	122.8 (4)
C45—C44—C34	122.9 (3)	C115—C114—C113	115.4 (4)
C43—C44—C34	122.7 (3)	C115—C114—C124	122.1 (3)
C44—C45—C46	123.3 (4)	C113—C114—C124	122.5 (3)
C45—C46—C41	121.2 (4)	C116—C115—C114	123.3 (4)
O5—C51—C56	123.7 (4)	C115—C116—C111	119.6 (4)
O5—C51—C52	117.7 (4)	O12—C121—C126	123.6 (4)
C56—C51—C52	118.6 (4)	O12—C121—C122	118.5 (4)
C51—C52—C53	120.4 (4)	C126—C121—C122	117.8 (4)
C54—C53—C52	122.3 (4)	C123—C122—C121	121.0 (4)
C55—C54—C53	115.4 (4)	C122—C123—C124	122.2 (4)
C55—C54—C64	123.1 (4)	C125—C124—C123	115.2 (4)
C53—C54—C64	121.5 (4)	C125—C124—C114	122.7 (4)
C56—C55—C54	123.4 (4)	C123—C124—C114	122.1 (4)
C51—C56—C55	119.9 (4)	C126—C125—C124	122.9 (4)
O6—C61—C66	119.3 (4)	C125—C126—C121	120.9 (4)
C5A—N1—C1A—C2A	159.4 (4)	C55—C54—C64—C65	−175.4 (4)
C3A—N1—C1A—C2A	−77.9 (5)	C53—C54—C64—C65	6.1 (6)
N1—C1A—C2A—N11	−64.5 (5)	C55—C54—C64—C63	6.5 (6)
C5A—N1—C3A—C4A	−82.7 (5)	C53—C54—C64—C63	−172.0 (5)
C1A—N1—C3A—C4A	154.1 (4)	C63—C64—C65—C66	0.1 (7)
N1—C3A—C4A—N12	−64.8 (5)	C54—C64—C65—C66	−178.1 (4)
C3A—N1—C5A—C6A	159.2 (4)	O6—C61—C66—C65	176.9 (4)
C1A—N1—C5A—C6A	−77.7 (5)	C62—C61—C66—C65	−1.4 (7)
N1—C5A—C6A—N13	−60.8 (5)	C64—C65—C66—C61	1.1 (8)
C5B—N2—C1B—C2B	79.7 (5)	O7—C71—C72—C73	179.9 (4)
C3B—N2—C1B—C2B	−156.1 (4)	C76—C71—C72—C73	0.7 (7)
N2—C1B—C2B—N21	66.4 (5)	C71—C72—C73—C74	0.3 (7)
C5B—N2—C3B—C4B	−157.8 (4)	C72—C73—C74—C75	−1.3 (7)
C1B—N2—C3B—C4B	79.7 (5)	C72—C73—C74—C84	177.1 (4)
N2—C3B—C4B—N22	70.5 (5)	C73—C74—C75—C76	1.3 (7)
C3B—N2—C5B—C6B	75.6 (5)	C84—C74—C75—C76	−177.1 (5)
C1B—N2—C5B—C6B	−161.0 (4)	O7—C71—C76—C75	180.0 (5)
N2—C5B—C6B—N23	59.9 (6)	C72—C71—C76—C75	−0.8 (7)
O1—C11—C12—C13	178.9 (5)	C74—C75—C76—C71	−0.3 (8)
C16—C11—C12—C13	0.0 (8)	O8—C81—C82—C83	−177.9 (4)
C11—C12—C13—C14	−0.8 (8)	C86—C81—C82—C83	2.6 (7)
C12—C13—C14—C15	1.4 (7)	C81—C82—C83—C84	−0.5 (7)
C12—C13—C14—C24	−178.5 (4)	C82—C83—C84—C85	−1.8 (7)
C13—C14—C15—C16	−1.2 (6)	C82—C83—C84—C74	176.5 (4)
C24—C14—C15—C16	178.7 (4)	C73—C74—C84—C85	15.7 (6)
C12—C11—C16—C15	0.1 (7)	C75—C74—C84—C85	−166.1 (5)
O1—C11—C16—C15	−178.8 (4)	C73—C74—C84—C83	−162.5 (4)
C14—C15—C16—C11	0.5 (7)	C75—C74—C84—C83	15.7 (6)
O2—C21—C22—C23	−179.1 (4)	C83—C84—C85—C86	2.2 (7)
C26—C21—C22—C23	−0.4 (7)	C74—C84—C85—C86	−176.0 (4)
C21—C22—C23—C24	0.0 (7)	O8—C81—C86—C85	178.4 (4)
C22—C23—C24—C25	0.0 (6)	C82—C81—C86—C85	−2.2 (7)
C22—C23—C24—C14	−179.1 (4)	C84—C85—C86—C81	−0.2 (8)
C15—C14—C24—C25	167.7 (4)	O9—C91—C92—C93	178.8 (4)
C13—C14—C24—C25	−12.5 (6)	C96—C91—C92—C93	1.7 (7)
C15—C14—C24—C23	−13.3 (6)	C91—C92—C93—C94	−0.6 (7)
C13—C14—C24—C23	166.5 (4)	C92—C93—C94—C95	−1.1 (6)
C23—C24—C25—C26	0.5 (6)	C92—C93—C94—C104	179.6 (4)
C14—C24—C25—C26	179.6 (4)	C93—C94—C95—C96	1.8 (7)
C24—C25—C26—C21	−0.9 (7)	C104—C94—C95—C96	−178.9 (4)
C22—C21—C26—C25	0.8 (6)	C94—C95—C96—C91	−0.8 (8)
O2—C21—C26—C25	179.5 (4)	O9—C91—C96—C95	−178.3 (4)
O3—C31—C32—C33	179.8 (5)	C92—C91—C96—C95	−1.0 (7)
C36—C31—C32—C33	0.4 (8)	C106—C101—C102—C103	0.3 (7)
C31—C32—C33—C34	−1.8 (10)	O10—C101—C102—C103	−178.6 (4)
C32—C33—C34—C35	2.6 (8)	C101—C102—C103—C104	−0.6 (7)
C32—C33—C34—C44	−178.0 (5)	C102—C103—C104—C105	0.0 (7)
C33—C34—C35—C36	−2.1 (8)	C102—C103—C104—C94	179.9 (4)
C44—C34—C35—C36	178.4 (5)	C95—C94—C104—C105	−171.3 (5)
C34—C35—C36—C31	1.0 (9)	C93—C94—C104—C105	7.9 (6)
O3—C31—C36—C35	−179.4 (5)	C95—C94—C104—C103	8.8 (6)
C32—C31—C36—C35	0.0 (8)	C93—C94—C104—C103	−172.0 (4)
O4—C41—C42—C43	−178.9 (5)	C103—C104—C105—C106	0.9 (7)
C46—C41—C42—C43	1.4 (8)	C94—C104—C105—C106	−179.0 (4)
C41—C42—C43—C44	−0.2 (9)	O10—C101—C106—C105	179.5 (5)
C42—C43—C44—C45	−2.0 (8)	C102—C101—C106—C105	0.6 (7)
C42—C43—C44—C34	178.0 (5)	C104—C105—C106—C101	−1.2 (8)
C35—C34—C44—C45	−179.6 (5)	O11—C111—C112—C113	−179.1 (4)
C33—C34—C44—C45	0.9 (6)	C116—C111—C112—C113	1.1 (7)
C35—C34—C44—C43	0.3 (6)	C111—C112—C113—C114	0.7 (8)
C33—C34—C44—C43	−179.1 (5)	C112—C113—C114—C115	−1.5 (7)
C43—C44—C45—C46	3.2 (8)	C112—C113—C114—C124	176.9 (4)
C34—C44—C45—C46	−176.9 (5)	C113—C114—C115—C116	0.6 (7)
C44—C45—C46—C41	−2.1 (9)	C124—C114—C115—C116	−177.9 (4)
C42—C41—C46—C45	−0.3 (8)	C114—C115—C116—C111	1.1 (8)
O4—C41—C46—C45	179.9 (5)	O11—C111—C116—C115	178.2 (4)
O5—C51—C52—C53	−179.6 (5)	C112—C111—C116—C115	−2.0 (7)
C56—C51—C52—C53	−0.5 (8)	O12—C121—C122—C123	−179.5 (5)
C51—C52—C53—C54	−0.1 (9)	C126—C121—C122—C123	1.5 (8)
C52—C53—C54—C55	0.3 (7)	C121—C122—C123—C124	0.1 (9)
C52—C53—C54—C64	178.9 (5)	C122—C123—C124—C125	−2.2 (8)
C53—C54—C55—C56	0.1 (7)	C122—C123—C124—C114	178.8 (5)
C64—C54—C55—C56	−178.5 (4)	C115—C114—C124—C125	170.7 (4)
O5—C51—C56—C55	179.9 (4)	C113—C114—C124—C125	−7.6 (6)
C52—C51—C56—C55	0.8 (7)	C115—C114—C124—C123	−10.4 (6)
C54—C55—C56—C51	−0.7 (8)	C113—C114—C124—C123	171.3 (5)
O6—C61—C62—C63	−177.7 (5)	C123—C124—C125—C126	2.8 (7)
C66—C61—C62—C63	0.4 (7)	C114—C124—C125—C126	−178.2 (4)
C61—C62—C63—C64	0.8 (8)	C124—C125—C126—C121	−1.3 (7)
C62—C63—C64—C65	−1.1 (7)	O12—C121—C126—C125	−179.8 (4)
C62—C63—C64—C54	177.1 (5)	C122—C121—C126—C125	−1.0 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N12	0.82	1.85	2.666 (5)	172
O2—H2···O3	0.82	1.82	2.626 (4)	167
O5—H5···O4	0.82	1.81	2.620 (4)	168
O6—H6···N21	0.82	1.86	2.669 (5)	172
O7—H7···N22^i	0.82	1.88	2.677 (5)	163
O8—H8···O9	0.82	1.89	2.671 (5)	158
O9—H9···O4^i	0.82	1.71	2.502 (4)	162
O12—H12···N11^ii	0.82	1.86	2.639 (6)	157
O10—H10···O3^ii	0.82	1.70	2.496 (5)	162
O13—H13···O7	0.82	2.02	2.758 (5)	149
O11—H11···O10	0.82	1.90	2.705 (4)	169
N11—H11A···O1	0.89	2.28	3.154 (6)	166
N11—H11B···O8^iii	0.89	2.21	3.084 (5)	167
N13—H13A···O4^iv	0.89	1.93	2.780 (5)	158
N13—H13B···O1	0.89	2.08	2.880 (5)	150
N13—H13C···O14	0.89	1.88	2.746 (7)	163
O14—H14···O12^v	0.82	1.86	2.660 (6)	163
N22—H22B···O6	0.89	2.22	3.102 (5)	171
N23—H23A···O3^vi	0.89	1.95	2.788 (5)	156
N23—H23B···O13	0.89	2.01	2.805 (6)	147
N23—H23C···O6	0.89	2.05	2.856 (5)	150

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