Supramolecular organic frameworks of a Schiff base showing selective guest adsorption

A relatively simple molecule, N,N′-bis(3-methoxy-4-hydroxybenzylidene)-1,4-phenylenediamine, was synthesized and found to be a suitable building block to form different types of crystalline framework via hydrogen bonding. The porous frameworks show potential selectivity for uptake of small guest molecules.

Computing details

For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

(wang12a)

Crystal data

C28H26N2O4	V = 1236.39 (14) Å^3
Mr = 454.51	Z = 2
a = 5.9038 (4) Å	F(000) = 480
b = 10.7455 (8) Å	Dx = 1.221 Mg m^−3
c = 19.4895 (11) Å	Mo Kα radiation, λ = 0.71073 Å
α = 90°	µ = 0.08 mm^−1
β = 90.263 (2)°	T = 193 K
γ = 90°	0.51 × 0.37 × 0.24 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 27.5°, θmin = 2.8°
2813 measured reflections	h = 0→7
2813 independent reflections	k = 0→13
2089 reflections with I > 2σ(I)	l = −25→25

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.072P)^2] where P = (Fo^2 + 2Fc^2)/3
2813 reflections	(Δ/σ)max < 0.001
206 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.98302 (15)	0.38347 (8)	0.17400 (4)	0.0357 (2)
O2	0.69333 (17)	0.57606 (9)	0.17414 (5)	0.0507 (3)
N1	0.92501 (16)	0.82976 (9)	0.39222 (5)	0.0320 (2)
C1	1.00558 (19)	0.47429 (11)	0.22198 (5)	0.0315 (3)
C2	1.1820 (2)	0.46792 (12)	0.26862 (6)	0.0377 (3)
H2	1.290 (2)	0.3996 (14)	0.2660 (7)	0.043 (4)*
C3	1.2061 (2)	0.55842 (12)	0.31913 (6)	0.0381 (3)
H3	1.335 (2)	0.5556 (14)	0.3524 (7)	0.046 (4)*
C4	1.05146 (19)	0.65605 (11)	0.32380 (6)	0.0334 (3)
C5	0.8756 (2)	0.66417 (12)	0.27543 (6)	0.0367 (3)
H5	0.767 (2)	0.7295 (14)	0.2771 (7)	0.044 (4)*
C6	0.8545 (2)	0.57555 (11)	0.22470 (6)	0.0344 (3)
C7	1.0738 (2)	0.74619 (11)	0.37922 (6)	0.0331 (3)
H7	1.215 (2)	0.7353 (12)	0.4073 (7)	0.035 (3)*
C8	0.96845 (19)	0.91411 (10)	0.44686 (5)	0.0305 (3)
C9	1.17743 (19)	0.97167 (12)	0.45630 (6)	0.0341 (3)
H9	1.296 (2)	0.9545 (14)	0.4255 (7)	0.043 (4)*
C10	0.7908 (2)	0.94442 (12)	0.49044 (6)	0.0344 (3)
H10	0.646 (2)	0.9052 (13)	0.4844 (7)	0.041 (3)*
C11	0.5473 (3)	0.68213 (15)	0.17094 (9)	0.0549 (4)
H11C	0.448 (3)	0.6681 (16)	0.1328 (10)	0.067 (5)*
H11B	0.641 (3)	0.7595 (18)	0.1667 (9)	0.065 (5)*
H11A	0.460 (3)	0.6868 (19)	0.2159 (12)	0.079 (6)*
C12	0.4681 (4)	0.6122 (3)	0.53331 (15)	0.1003 (8)
H12	0.445 (5)	0.693 (3)	0.5601 (17)	0.143 (12)*
C13	0.6592 (4)	0.5910 (3)	0.49552 (17)	0.1089 (10)
H13	0.791 (5)	0.651 (3)	0.4900 (16)	0.136 (10)*
C14	0.6912 (4)	0.4813 (4)	0.46258 (16)	0.1067 (9)
H14	0.813 (5)	0.464 (3)	0.4363 (14)	0.136 (10)*
H1	0.842 (4)	0.3859 (19)	0.1542 (10)	0.076 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0382 (5)	0.0317 (4)	0.0373 (4)	0.0005 (3)	−0.0011 (4)	−0.0083 (3)
O2	0.0641 (6)	0.0415 (6)	0.0462 (5)	0.0170 (4)	−0.0263 (5)	−0.0153 (4)
N1	0.0372 (5)	0.0328 (5)	0.0259 (4)	0.0003 (4)	−0.0047 (4)	−0.0025 (4)
C1	0.0365 (6)	0.0284 (6)	0.0296 (5)	−0.0030 (4)	0.0033 (4)	−0.0025 (4)
C2	0.0355 (6)	0.0326 (6)	0.0450 (7)	0.0044 (5)	−0.0021 (5)	−0.0054 (5)
C3	0.0365 (6)	0.0378 (7)	0.0398 (6)	0.0022 (5)	−0.0079 (5)	−0.0040 (5)
C4	0.0379 (6)	0.0320 (6)	0.0302 (5)	−0.0003 (5)	−0.0018 (5)	−0.0014 (5)
C5	0.0434 (6)	0.0326 (6)	0.0339 (6)	0.0073 (5)	−0.0057 (5)	−0.0049 (5)
C6	0.0405 (6)	0.0324 (6)	0.0302 (5)	0.0021 (5)	−0.0060 (5)	−0.0017 (5)
C7	0.0368 (6)	0.0336 (6)	0.0288 (5)	0.0006 (5)	−0.0048 (4)	−0.0007 (5)
C8	0.0354 (6)	0.0314 (6)	0.0246 (5)	0.0029 (4)	−0.0075 (4)	−0.0019 (4)
C9	0.0326 (6)	0.0410 (7)	0.0285 (5)	0.0024 (5)	−0.0015 (4)	−0.0050 (5)
C10	0.0312 (5)	0.0384 (7)	0.0334 (6)	−0.0008 (5)	−0.0051 (4)	−0.0041 (5)
C11	0.0662 (10)	0.0436 (8)	0.0545 (9)	0.0168 (7)	−0.0278 (8)	−0.0084 (7)
C12	0.0844 (15)	0.104 (2)	0.1125 (19)	−0.0038 (14)	0.0003 (14)	0.0471 (17)
C13	0.0772 (15)	0.108 (2)	0.141 (2)	−0.0220 (15)	0.0082 (15)	0.055 (2)
C14	0.0642 (13)	0.129 (2)	0.127 (2)	−0.0020 (15)	0.0131 (13)	0.057 (2)

Geometric parameters (Å, º)

O1—C1	1.3577 (13)	C4—C7	1.4563 (16)
O2—C6	1.3668 (14)	C5—C6	1.3780 (16)
O2—C11	1.4303 (17)	C8—C10	1.3913 (17)
N1—C7	1.2823 (15)	C8—C9	1.3915 (16)
N1—C8	1.4209 (14)	C9—C10^i	1.3871 (16)
C1—C2	1.3811 (16)	C10—C9^i	1.3871 (16)
C1—C6	1.4079 (16)	C12—C13	1.369 (4)
C2—C3	1.3906 (17)	C12—C14^ii	1.379 (4)
C3—C4	1.3938 (17)	C13—C14	1.355 (4)
C4—C5	1.4019 (16)	C14—C12^ii	1.379 (4)
C6—O2—C11	116.89 (10)	O2—C6—C1	114.52 (10)
C7—N1—C8	118.25 (9)	C5—C6—C1	120.40 (10)
O1—C1—C2	119.28 (10)	N1—C7—C4	123.54 (10)
O1—C1—C6	121.42 (10)	C10—C8—C9	119.06 (10)
C2—C1—C6	119.30 (10)	C10—C8—N1	118.22 (10)
C1—C2—C3	120.37 (11)	C9—C8—N1	122.64 (10)
C2—C3—C4	120.53 (11)	C10^i—C9—C8	120.30 (10)
C3—C4—C5	119.08 (11)	C9^i—C10—C8	120.61 (11)
C3—C4—C7	119.47 (10)	C13—C12—C14^ii	118.3 (3)
C5—C4—C7	121.44 (10)	C14—C13—C12	121.1 (3)
C6—C5—C4	120.24 (11)	C13—C14—C12^ii	120.6 (3)
O2—C6—C5	125.08 (11)
O1—C1—C2—C3	−178.68 (11)	O1—C1—C6—C5	177.55 (10)
C6—C1—C2—C3	2.06 (18)	C2—C1—C6—C5	−3.21 (18)
C1—C2—C3—C4	0.60 (19)	C8—N1—C7—C4	−178.71 (10)
C2—C3—C4—C5	−2.14 (19)	C3—C4—C7—N1	−171.44 (12)
C2—C3—C4—C7	176.97 (11)	C5—C4—C7—N1	7.64 (19)
C3—C4—C5—C6	0.99 (19)	C7—N1—C8—C10	−138.34 (12)
C7—C4—C5—C6	−178.09 (11)	C7—N1—C8—C9	44.86 (16)
C11—O2—C6—C5	5.1 (2)	C10—C8—C9—C10^i	1.68 (19)
C11—O2—C6—C1	−174.91 (13)	N1—C8—C9—C10^i	178.46 (11)
C4—C5—C6—O2	−178.37 (12)	C9—C8—C10—C9^i	−1.68 (19)
C4—C5—C6—C1	1.67 (18)	N1—C8—C10—C9^i	−178.61 (10)
O1—C1—C6—O2	−2.41 (16)	C14^ii—C12—C13—C14	0.4 (4)
C2—C1—C6—O2	176.83 (11)	C12—C13—C14—C12^ii	−0.4 (5)

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

(wang13a)

Crystal data

C24H22Cl6N2O4	V = 1400.50 (11) Å^3
Mr = 615.14	Z = 2
a = 6.8524 (3) Å	F(000) = 628
b = 11.9655 (5) Å	Dx = 1.459 Mg m^−3
c = 17.3274 (8) Å	Mo Kα radiation, λ = 0.71073 Å
α = 90°	µ = 0.65 mm^−1
β = 99.6780 (11)°	T = 193 K
γ = 90°	0.36 × 0.25 × 0.20 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 27.5°, θmin = 2.1°
3190 measured reflections	h = 0→8
3190 independent reflections	k = 0→15
1828 reflections with I > 2σ(I)	l = −22→22

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.183	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ^2(Fo^2) + (0.1157P)^2] where P = (Fo^2 + 2Fc^2)/3
3190 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.56 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	1.0349 (10)	0.7239 (10)	−0.0001 (8)	0.156 (3)	0.73 (4)
Cl2	1.0462 (9)	0.5887 (6)	0.1415 (3)	0.098 (2)	0.44 (3)
Cl3	0.6933 (7)	0.6494 (4)	0.0541 (3)	0.1031 (17)	0.524 (15)
C12	0.9335 (18)	0.6091 (11)	0.0360 (8)	0.050 (4)	0.231 (10)
H12A	0.9337	0.5406	0.0030	0.060*	0.231 (10)
Cl1`	1.041 (3)	0.700 (2)	−0.0128 (11)	0.146 (5)	0.27 (4)
Cl2`	1.0847 (17)	0.5637 (12)	0.1188 (12)	0.190 (4)	0.56 (3)
Cl3`	0.6903 (10)	0.6137 (14)	0.0339 (8)	0.216 (4)	0.476 (15)
C12`	0.9134 (11)	0.6877 (6)	0.0855 (6)	0.132 (4)	0.769 (10)
H12B	0.9032	0.7534	0.1202	0.159*	0.769 (10)
O1	0.0800 (3)	0.09820 (16)	0.17577 (12)	0.0438 (5)
H1	0.135 (7)	0.102 (4)	0.152 (3)	0.085 (16)*
O2	0.3331 (3)	−0.07374 (16)	0.18351 (12)	0.0571 (6)
N1	0.0845 (3)	−0.34653 (17)	0.38696 (11)	0.0361 (5)
C1	0.0572 (4)	0.0090 (2)	0.22116 (14)	0.0378 (6)
C11	0.4521 (5)	−0.1683 (2)	0.1764 (2)	0.0655 (9)
H11C	0.5503	−0.1497	0.1433	0.098*
H11B	0.3685	−0.2298	0.1525	0.098*
H11A	0.5199	−0.1910	0.2284	0.098*
C2	−0.0956 (4)	0.0085 (2)	0.26281 (17)	0.0494 (7)
H2	−0.189 (5)	0.067 (3)	0.2537 (19)	0.064 (9)*
C3	−0.1221 (5)	−0.0806 (2)	0.31062 (18)	0.0516 (7)
H3	−0.223 (5)	−0.085 (3)	0.3324 (19)	0.057 (9)*
C4	0.0049 (4)	−0.1715 (2)	0.31803 (15)	0.0423 (6)
C5	0.1595 (4)	−0.1712 (2)	0.27478 (15)	0.0412 (6)
H5	0.235 (3)	−0.219 (2)	0.2785 (13)	0.026 (6)*
C6	0.1861 (4)	−0.0834 (2)	0.22695 (14)	0.0393 (6)
C7	−0.0234 (4)	−0.2601 (2)	0.37227 (15)	0.0422 (6)
H7	−0.123 (4)	−0.247 (2)	0.3996 (17)	0.049 (8)*
C8	0.0368 (3)	−0.42326 (19)	0.44352 (13)	0.0342 (5)
C9	0.1915 (4)	−0.4735 (2)	0.49299 (14)	0.0385 (6)
H9	0.317 (4)	−0.459 (2)	0.4862 (16)	0.042 (7)*
C10	−0.1564 (4)	−0.4512 (2)	0.45057 (14)	0.0373 (6)
H10	−0.261 (4)	−0.422 (2)	0.4189 (15)	0.034 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.115 (3)	0.139 (3)	0.231 (6)	0.036 (2)	0.080 (3)	0.120 (4)
Cl2	0.087 (2)	0.103 (3)	0.090 (4)	−0.049 (3)	−0.0219 (16)	0.030 (3)
Cl3	0.106 (3)	0.114 (3)	0.104 (2)	0.044 (2)	0.059 (2)	0.0506 (17)
C12	0.061 (8)	0.030 (7)	0.061 (8)	−0.007 (5)	0.015 (6)	−0.002 (5)
Cl1`	0.152 (10)	0.163 (10)	0.150 (9)	−0.009 (8)	0.102 (8)	0.013 (12)
Cl2`	0.139 (4)	0.169 (5)	0.238 (8)	0.007 (5)	−0.035 (5)	0.126 (5)
Cl3`	0.106 (4)	0.306 (10)	0.208 (6)	−0.060 (5)	−0.053 (4)	0.158 (6)
C12`	0.119 (6)	0.083 (5)	0.181 (9)	−0.024 (4)	−0.015 (5)	0.056 (5)
O1	0.0476 (11)	0.0368 (10)	0.0495 (11)	−0.0003 (8)	0.0147 (9)	0.0116 (8)
O2	0.0690 (12)	0.0412 (11)	0.0719 (13)	0.0100 (9)	0.0427 (11)	0.0136 (9)
N1	0.0435 (11)	0.0350 (10)	0.0315 (10)	0.0018 (9)	0.0114 (8)	0.0036 (8)
C1	0.0446 (13)	0.0307 (12)	0.0376 (13)	−0.0021 (10)	0.0056 (10)	0.0036 (10)
C11	0.070 (2)	0.0438 (16)	0.095 (2)	0.0109 (14)	0.0483 (18)	0.0050 (16)
C2	0.0536 (16)	0.0391 (14)	0.0591 (17)	0.0133 (13)	0.0200 (13)	0.0135 (13)
C3	0.0555 (16)	0.0475 (16)	0.0585 (17)	0.0121 (14)	0.0287 (14)	0.0143 (13)
C4	0.0536 (14)	0.0372 (13)	0.0386 (13)	0.0061 (11)	0.0149 (11)	0.0066 (11)
C5	0.0493 (15)	0.0316 (13)	0.0449 (15)	0.0100 (12)	0.0144 (11)	0.0048 (11)
C6	0.0456 (13)	0.0357 (13)	0.0391 (13)	−0.0008 (11)	0.0142 (10)	−0.0004 (10)
C7	0.0517 (15)	0.0399 (14)	0.0388 (14)	0.0048 (12)	0.0189 (11)	0.0052 (11)
C8	0.0456 (13)	0.0304 (11)	0.0293 (11)	0.0056 (10)	0.0143 (9)	0.0009 (9)
C9	0.0378 (13)	0.0404 (13)	0.0400 (13)	0.0025 (11)	0.0146 (10)	0.0010 (11)
C10	0.0381 (13)	0.0401 (13)	0.0336 (13)	0.0089 (11)	0.0058 (10)	0.0050 (10)

Geometric parameters (Å, º)

Cl1—C12	1.705 (14)	C1—C2	1.368 (4)
Cl2—C12	1.877 (14)	C1—C6	1.407 (3)
Cl3—C12	1.793 (13)	C2—C3	1.380 (4)
Cl1`—C12`	2.045 (18)	C3—C4	1.386 (4)
Cl2`—C12`	1.919 (15)	C4—C5	1.396 (4)
Cl3`—C12`	1.860 (13)	C4—C7	1.451 (3)
O1—C1	1.351 (3)	C5—C6	1.370 (3)
O2—C6	1.360 (3)	C8—C9	1.384 (3)
O2—C11	1.412 (3)	C8—C10	1.390 (3)
N1—C7	1.272 (3)	C9—C10^i	1.380 (3)
N1—C8	1.421 (3)	C10—C9^i	1.380 (3)
Cl1—C12—Cl3	106.9 (8)	C3—C4—C5	118.0 (2)
Cl1—C12—Cl2	109.6 (8)	C3—C4—C7	118.9 (2)
Cl3—C12—Cl2	96.0 (7)	C5—C4—C7	123.1 (2)
Cl3`—C12`—Cl2`	100.9 (7)	C6—C5—C4	121.1 (2)
Cl3`—C12`—Cl1`	93.7 (9)	O2—C6—C5	125.9 (2)
Cl2`—C12`—Cl1`	88.9 (11)	O2—C6—C1	114.1 (2)
C6—O2—C11	118.2 (2)	C5—C6—C1	120.0 (2)
C7—N1—C8	118.0 (2)	N1—C7—C4	125.9 (2)
O1—C1—C2	119.0 (2)	C9—C8—C10	118.9 (2)
O1—C1—C6	122.0 (2)	C9—C8—N1	117.8 (2)
C2—C1—C6	119.0 (2)	C10—C8—N1	123.3 (2)
C1—C2—C3	120.6 (3)	C10^i—C9—C8	121.1 (2)
C2—C3—C4	121.2 (3)	C9^i—C10—C8	120.0 (2)
O1—C1—C2—C3	−179.1 (3)	C2—C1—C6—O2	−179.7 (2)
C6—C1—C2—C3	0.8 (4)	O1—C1—C6—C5	178.9 (2)
C1—C2—C3—C4	0.2 (5)	C2—C1—C6—C5	−1.1 (4)
C2—C3—C4—C5	−0.8 (5)	C8—N1—C7—C4	178.5 (2)
C2—C3—C4—C7	176.7 (3)	C3—C4—C7—N1	−177.7 (3)
C3—C4—C5—C6	0.6 (4)	C5—C4—C7—N1	−0.3 (4)
C7—C4—C5—C6	−176.9 (3)	C7—N1—C8—C9	−142.2 (2)
C11—O2—C6—C5	10.6 (4)	C7—N1—C8—C10	38.8 (3)
C11—O2—C6—C1	−170.9 (3)	C10—C8—C9—C10^i	−1.0 (4)
C4—C5—C6—O2	178.8 (3)	N1—C8—C9—C10^i	179.9 (2)
C4—C5—C6—C1	0.4 (4)	C9—C8—C10—C9^i	1.0 (4)
O1—C1—C6—O2	0.3 (3)	N1—C8—C10—C9^i	−180.0 (2)

Symmetry code: (i) −x, −y−1, −z+1.

(w22)

Crystal data

C26H28N2O5	V = 2672.8 (3) Å^3
Mr = 448.50	Z = 4
a = 13.2363 (9) Å	F(000) = 952
b = 11.7650 (8) Å	Dx = 1.115 Mg m^−3
c = 17.6353 (9) Å	Mo Kα radiation, λ = 0.71073 Å
α = 90°	µ = 0.08 mm^−1
β = 103.281 (1)°	T = 193 K
γ = 90°	0.42 × 0.41 × 0.39 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 27.5°, θmin = 2.3°
6100 measured reflections	h = 0→17
6100 independent reflections	k = 0→15
3932 reflections with I > 2σ(I)	l = −22→22

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)] = 0.102	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.304	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
6100 reflections	(Δ/σ)max < 0.001
378 parameters	Δρmax = 1.54 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.06217 (15)	0.34439 (16)	0.18641 (11)	0.0399 (5)
O2	−0.05483 (18)	0.53189 (19)	0.16787 (13)	0.0573 (7)
O3	0.45358 (17)	1.57240 (18)	0.83135 (12)	0.0434 (5)
H3O	0.521 (4)	1.582 (4)	0.841 (2)	0.072 (12)*
O4	0.58461 (15)	1.42111 (18)	0.79202 (13)	0.0462 (6)
O5	0.5788 (2)	0.3694 (3)	0.50586 (18)	0.0872 (10)
N1	0.13553 (17)	0.7971 (2)	0.40008 (13)	0.0375 (6)
N2	0.33754 (17)	1.13198 (19)	0.61093 (12)	0.0350 (5)
C1	−0.1076 (3)	0.6355 (3)	0.1468 (2)	0.0572 (10)
H1B	−0.165 (3)	0.612 (3)	0.105 (2)	0.063 (11)*
H1A	−0.143 (3)	0.664 (4)	0.182 (3)	0.072 (13)*
H1C	−0.064 (4)	0.699 (4)	0.150 (2)	0.082 (14)*
C2	0.1862 (2)	0.7064 (2)	0.39368 (17)	0.0412 (7)
H2	0.248 (3)	0.694 (3)	0.4290 (19)	0.044 (8)*
C3	0.2866 (2)	1.2148 (3)	0.63029 (16)	0.0397 (6)
H3	0.212 (3)	1.216 (3)	0.6028 (18)	0.046 (8)*
C4	0.6558 (3)	1.3418 (3)	0.7736 (3)	0.0588 (9)
H4C	0.724 (3)	1.372 (3)	0.8033 (18)	0.040 (8)*
H4A	0.664 (5)	1.264 (6)	0.705 (4)	0.17 (2)*
H4B	0.639 (3)	1.276 (4)	0.795 (2)	0.070 (12)*
C11	0.0897 (2)	0.4332 (2)	0.23595 (16)	0.0364 (6)
C12	0.0303 (2)	0.5331 (2)	0.22824 (15)	0.0386 (6)
C13	0.0601 (2)	0.6227 (3)	0.27865 (17)	0.0418 (7)
H13	0.029 (3)	0.701 (4)	0.270 (2)	0.080 (13)*
C14	0.1507 (2)	0.6146 (2)	0.33875 (16)	0.0400 (6)
C15	0.2094 (2)	0.5157 (3)	0.34489 (19)	0.0475 (8)
H15	0.277 (3)	0.509 (3)	0.3832 (19)	0.047 (9)*
C16	0.1795 (2)	0.4263 (3)	0.29391 (19)	0.0448 (7)
H16	0.228 (3)	0.357 (3)	0.299 (2)	0.066 (11)*
C21	0.1876 (2)	0.8799 (2)	0.45469 (15)	0.0342 (6)
C22	0.1347 (2)	0.9305 (2)	0.50471 (16)	0.0373 (6)
H22	0.057 (3)	0.896 (4)	0.518 (2)	0.079 (13)*
C23	0.1817 (2)	1.0132 (2)	0.55725 (15)	0.0370 (6)
H23	0.138 (3)	1.035 (3)	0.597 (2)	0.061 (10)*
C24	0.2832 (2)	1.0481 (2)	0.55924 (14)	0.0327 (6)
C25	0.3364 (2)	0.9967 (2)	0.50878 (16)	0.0373 (6)
H25	0.408 (3)	1.018 (3)	0.5073 (19)	0.050 (9)*
C26	0.2892 (2)	0.9141 (2)	0.45672 (16)	0.0385 (6)
H26	0.323 (2)	0.884 (3)	0.4195 (19)	0.045 (9)*
C31	0.4155 (2)	1.4855 (2)	0.78296 (15)	0.0364 (6)
C32	0.4819 (2)	1.4040 (2)	0.76090 (15)	0.0346 (6)
C33	0.4406 (2)	1.3161 (2)	0.71138 (15)	0.0362 (6)
H33	0.491 (3)	1.248 (3)	0.691 (2)	0.069 (11)*
C34	0.3330 (2)	1.3066 (2)	0.68307 (16)	0.0379 (6)
C35	0.2686 (2)	1.3869 (3)	0.70544 (19)	0.0471 (7)
H35	0.196 (3)	1.383 (3)	0.6896 (17)	0.040 (8)*
C36	0.3099 (2)	1.4750 (3)	0.75492 (19)	0.0465 (7)
H36	0.264 (3)	1.530 (4)	0.781 (2)	0.073 (12)*
C41	0.4907 (4)	0.3032 (5)	0.5085 (3)	0.0864 (14)
H41A	0.4483	0.3409	0.5407	0.104*
H41B	0.5116	0.2272	0.5307	0.104*
C42	0.4300 (5)	0.2931 (6)	0.4246 (4)	0.122 (2)
H42A	0.3557	0.3100	0.4205	0.146*
H42B	0.4361	0.2153	0.4047	0.146*
C43	0.4776 (4)	0.3800 (5)	0.3781 (3)	0.0837 (13)
H43A	0.4776	0.3512	0.3254	0.100*
H43B	0.4397	0.4532	0.3734	0.100*
C44	0.5871 (4)	0.3928 (6)	0.4269 (3)	0.0961 (16)
H44A	0.6344	0.3380	0.4102	0.115*
H44B	0.6133	0.4708	0.4226	0.115*
H1O	−0.021 (3)	0.350 (3)	0.151 (2)	0.068 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0377 (10)	0.0305 (10)	0.0480 (11)	0.0003 (8)	0.0026 (8)	−0.0074 (8)
O2	0.0604 (14)	0.0386 (12)	0.0556 (13)	0.0123 (10)	−0.0224 (10)	−0.0127 (10)
O3	0.0356 (11)	0.0375 (11)	0.0538 (12)	−0.0039 (9)	0.0034 (8)	−0.0147 (9)
O4	0.0320 (10)	0.0444 (12)	0.0573 (12)	−0.0028 (9)	0.0000 (8)	−0.0147 (9)
O5	0.074 (2)	0.105 (2)	0.0715 (19)	0.0031 (18)	−0.0051 (14)	−0.0004 (17)
N1	0.0370 (12)	0.0347 (12)	0.0359 (11)	−0.0002 (9)	−0.0020 (9)	−0.0070 (9)
N2	0.0340 (11)	0.0327 (12)	0.0344 (11)	−0.0035 (9)	0.0000 (8)	−0.0030 (9)
C1	0.064 (2)	0.0401 (18)	0.054 (2)	0.0124 (16)	−0.0158 (17)	−0.0033 (15)
C2	0.0387 (15)	0.0371 (15)	0.0403 (14)	0.0030 (12)	−0.0063 (11)	−0.0036 (11)
C3	0.0334 (14)	0.0395 (15)	0.0419 (14)	−0.0028 (11)	−0.0002 (10)	−0.0050 (11)
C4	0.0337 (17)	0.051 (2)	0.090 (3)	0.0001 (15)	0.0089 (16)	−0.0163 (19)
C11	0.0373 (14)	0.0297 (13)	0.0413 (14)	−0.0020 (11)	0.0071 (10)	−0.0021 (11)
C12	0.0394 (14)	0.0352 (14)	0.0362 (13)	0.0038 (11)	−0.0014 (10)	−0.0023 (11)
C13	0.0444 (15)	0.0335 (14)	0.0421 (15)	0.0077 (12)	−0.0012 (11)	−0.0055 (11)
C14	0.0397 (15)	0.0340 (14)	0.0413 (14)	0.0022 (11)	−0.0006 (11)	−0.0052 (11)
C15	0.0380 (15)	0.0394 (16)	0.0560 (18)	0.0046 (13)	−0.0080 (13)	−0.0073 (13)
C16	0.0387 (15)	0.0343 (15)	0.0570 (18)	0.0067 (12)	0.0019 (13)	−0.0047 (12)
C21	0.0349 (13)	0.0320 (13)	0.0312 (12)	0.0017 (10)	−0.0019 (9)	−0.0028 (10)
C22	0.0332 (13)	0.0362 (14)	0.0392 (14)	−0.0013 (11)	0.0011 (10)	−0.0044 (11)
C23	0.0360 (14)	0.0372 (14)	0.0357 (13)	0.0007 (11)	0.0038 (10)	−0.0054 (11)
C24	0.0320 (13)	0.0306 (13)	0.0318 (12)	−0.0007 (10)	−0.0006 (9)	−0.0001 (10)
C25	0.0304 (13)	0.0388 (14)	0.0409 (14)	−0.0005 (11)	0.0042 (10)	−0.0040 (11)
C26	0.0378 (14)	0.0370 (15)	0.0394 (14)	0.0031 (11)	0.0063 (11)	−0.0047 (11)
C31	0.0392 (14)	0.0307 (13)	0.0376 (14)	−0.0033 (11)	0.0052 (10)	−0.0045 (10)
C32	0.0324 (13)	0.0323 (13)	0.0370 (13)	−0.0020 (10)	0.0039 (10)	−0.0008 (10)
C33	0.0359 (14)	0.0333 (14)	0.0383 (13)	−0.0026 (11)	0.0063 (10)	−0.0036 (11)
C34	0.0363 (14)	0.0340 (14)	0.0406 (14)	−0.0011 (11)	0.0027 (11)	−0.0044 (11)
C35	0.0322 (15)	0.0453 (17)	0.0593 (18)	−0.0009 (13)	0.0011 (12)	−0.0142 (14)
C36	0.0355 (15)	0.0446 (17)	0.0571 (18)	0.0001 (12)	0.0056 (12)	−0.0151 (14)
C41	0.067 (3)	0.103 (4)	0.089 (3)	0.003 (3)	0.017 (2)	0.027 (3)
C42	0.127 (5)	0.109 (5)	0.110 (4)	−0.038 (4)	−0.014 (4)	0.004 (4)
C43	0.094 (3)	0.089 (3)	0.067 (3)	0.013 (3)	0.016 (2)	0.010 (2)
C44	0.092 (3)	0.120 (4)	0.080 (3)	0.013 (3)	0.027 (3)	0.012 (3)

Geometric parameters (Å, º)

O1—C11	1.357 (3)	C14—C15	1.390 (4)
O2—C12	1.361 (3)	C15—C16	1.381 (4)
O2—C1	1.412 (4)	C21—C22	1.381 (4)
O3—C31	1.353 (3)	C21—C26	1.396 (4)
O4—C32	1.359 (3)	C22—C23	1.388 (4)
O4—C4	1.417 (4)	C23—C24	1.397 (4)
O5—C41	1.412 (6)	C24—C25	1.393 (4)
O5—C44	1.448 (6)	C25—C26	1.383 (4)
N1—C2	1.279 (4)	C31—C36	1.377 (4)
N1—C21	1.430 (3)	C31—C32	1.414 (4)
N2—C3	1.276 (4)	C32—C33	1.383 (4)
N2—C24	1.421 (3)	C33—C34	1.401 (4)
C2—C14	1.455 (4)	C34—C35	1.389 (4)
C3—C34	1.465 (4)	C35—C36	1.384 (4)
C11—C16	1.381 (4)	C41—C42	1.517 (7)
C11—C12	1.403 (4)	C42—C43	1.533 (8)
C12—C13	1.377 (4)	C43—C44	1.513 (7)
C13—C14	1.409 (4)
C12—O2—C1	117.9 (2)	C22—C23—C24	120.3 (3)
C32—O4—C4	117.8 (2)	C25—C24—C23	118.7 (2)
C41—O5—C44	112.5 (4)	C25—C24—N2	117.1 (2)
C2—N1—C21	116.5 (2)	C23—C24—N2	124.2 (2)
C3—N2—C24	118.7 (2)	C26—C25—C24	120.7 (3)
N1—C2—C14	125.6 (2)	C25—C26—C21	120.4 (3)
N2—C3—C34	124.2 (3)	O3—C31—C36	119.6 (2)
O1—C11—C16	119.3 (2)	O3—C31—C32	121.3 (2)
O1—C11—C12	121.4 (2)	C36—C31—C32	119.0 (2)
C16—C11—C12	119.3 (2)	O4—C32—C33	125.4 (2)
O2—C12—C13	125.2 (3)	O4—C32—C31	114.6 (2)
O2—C12—C11	114.3 (2)	C33—C32—C31	120.0 (2)
C13—C12—C11	120.5 (2)	C32—C33—C34	120.5 (3)
C12—C13—C14	120.2 (3)	C35—C34—C33	119.0 (2)
C15—C14—C13	118.6 (3)	C35—C34—C3	119.1 (3)
C15—C14—C2	118.7 (2)	C33—C34—C3	122.0 (3)
C13—C14—C2	122.7 (3)	C36—C35—C34	120.6 (3)
C16—C15—C14	121.0 (3)	C31—C36—C35	120.9 (3)
C11—C16—C15	120.4 (3)	O5—C41—C42	105.5 (4)
C22—C21—C26	119.1 (2)	C41—C42—C43	106.2 (4)
C22—C21—N1	119.2 (2)	C44—C43—C42	102.6 (4)
C26—C21—N1	121.7 (2)	O5—C44—C43	104.7 (4)
C21—C22—C23	120.9 (3)
C21—N1—C2—C14	−176.2 (3)	C23—C24—C25—C26	1.1 (4)
C24—N2—C3—C34	179.9 (3)	N2—C24—C25—C26	179.9 (2)
C1—O2—C12—C13	10.9 (5)	C24—C25—C26—C21	−0.9 (4)
C1—O2—C12—C11	−168.2 (3)	C22—C21—C26—C25	0.7 (4)
O1—C11—C12—O2	−0.2 (4)	N1—C21—C26—C25	178.2 (2)
C16—C11—C12—O2	178.1 (3)	C4—O4—C32—C33	−1.0 (4)
O1—C11—C12—C13	−179.3 (3)	C4—O4—C32—C31	179.0 (3)
C16—C11—C12—C13	−1.1 (5)	O3—C31—C32—O4	0.0 (4)
O2—C12—C13—C14	−179.3 (3)	C36—C31—C32—O4	−179.5 (3)
C11—C12—C13—C14	−0.2 (5)	O3—C31—C32—C33	180.0 (3)
C12—C13—C14—C15	1.1 (5)	C36—C31—C32—C33	0.5 (4)
C12—C13—C14—C2	179.9 (3)	O4—C32—C33—C34	179.7 (3)
N1—C2—C14—C15	−172.7 (3)	C31—C32—C33—C34	−0.3 (4)
N1—C2—C14—C13	8.5 (5)	C32—C33—C34—C35	0.1 (4)
C13—C14—C15—C16	−0.7 (5)	C32—C33—C34—C3	179.8 (3)
C2—C14—C15—C16	−179.6 (3)	N2—C3—C34—C35	−174.3 (3)
O1—C11—C16—C15	179.8 (3)	N2—C3—C34—C33	6.0 (5)
C12—C11—C16—C15	1.4 (5)	C33—C34—C35—C36	0.0 (5)
C14—C15—C16—C11	−0.5 (5)	C3—C34—C35—C36	−179.7 (3)
C2—N1—C21—C22	−134.9 (3)	O3—C31—C36—C35	−179.9 (3)
C2—N1—C21—C26	47.6 (4)	C32—C31—C36—C35	−0.4 (5)
C26—C21—C22—C23	−0.9 (4)	C34—C35—C36—C31	0.2 (5)
N1—C21—C22—C23	−178.5 (2)	C44—O5—C41—C42	−6.4 (6)
C21—C22—C23—C24	1.3 (4)	O5—C41—C42—C43	−12.5 (7)
C22—C23—C24—C25	−1.3 (4)	C41—C42—C43—C44	25.4 (7)
C22—C23—C24—N2	−180.0 (2)	C41—O5—C44—C43	22.9 (6)
C3—N2—C24—C25	147.7 (3)	C42—C43—C44—O5	−28.7 (6)
C3—N2—C24—C23	−33.7 (4)

(w918a)

Crystal data

C32H28N4O4	V = 1322.91 (13) Å^3
Mr = 532.58	Z = 2
a = 12.8209 (9) Å	F(000) = 560
b = 7.0395 (4) Å	Dx = 1.337 Mg m^−3
c = 14.7623 (7) Å	Mo Kα radiation, λ = 0.71073 Å
α = 90°	µ = 0.09 mm^−1
β = 96.820 (3)°	T = 193 K
γ = 90°	0.48 × 0.25 × 0.23 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 27.5°, θmin = 1.6°
2967 measured reflections	h = 0→16
2967 independent reflections	k = 0→9
1798 reflections with I > 2σ(I)	l = −19→18

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)] = 0.073	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.195	w = 1/[σ^2(Fo^2) + (0.0825P)^2 + 0.5923P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2967 reflections	Δρmax = 0.31 e Å^−3
234 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: 0.012 (3)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.67498 (18)	0.7898 (3)	0.3732 (2)	0.0752 (7)
O2	0.72270 (15)	0.4264 (2)	0.41513 (14)	0.0572 (5)
N1	0.91058 (17)	0.1931 (4)	0.13974 (15)	0.0568 (6)
N2	0.6182 (2)	0.7156 (4)	0.5432 (2)	0.0851 (9)
C1	0.7343 (2)	0.6885 (4)	0.3198 (2)	0.0593 (8)
C2	0.7706 (3)	0.7748 (4)	0.2456 (2)	0.0683 (9)
H2	0.759 (2)	0.905 (5)	0.232 (2)	0.076 (9)*
C3	0.8271 (3)	0.6731 (5)	0.1880 (2)	0.0680 (9)
H3	0.858 (2)	0.737 (4)	0.137 (2)	0.068 (9)*
C4	0.8486 (2)	0.4810 (4)	0.20368 (19)	0.0558 (7)
C5	0.8150 (2)	0.3935 (4)	0.28021 (18)	0.0501 (6)
H5	0.829 (2)	0.253 (4)	0.293 (2)	0.065 (9)*
C6	0.75894 (19)	0.4955 (4)	0.33724 (19)	0.0502 (7)
C7	0.9016 (2)	0.3732 (4)	0.1374 (2)	0.0602 (8)
H7	0.933 (2)	0.451 (4)	0.094 (2)	0.061 (8)*
C8	0.9366 (2)	0.1563 (4)	−0.02293 (18)	0.0552 (7)
H8	0.887 (3)	0.269 (5)	−0.040 (2)	0.085 (10)*
C9	0.9557 (2)	0.1011 (4)	0.06861 (17)	0.0532 (7)
C10	1.0191 (2)	−0.0570 (4)	0.08960 (19)	0.0561 (7)
H10	1.032 (2)	−0.091 (4)	0.152 (2)	0.058 (8)*
C11	0.7458 (3)	0.2334 (4)	0.4372 (3)	0.0641 (8)
H11C	0.713 (2)	0.149 (5)	0.386 (2)	0.062 (9)*
H11A	0.826 (3)	0.220 (5)	0.446 (2)	0.079 (10)*
H11B	0.710 (3)	0.208 (6)	0.496 (3)	0.102 (12)*
C12	0.5952 (5)	0.8726 (6)	0.5856 (4)	0.143 (2)
H12A	0.6120	0.9900	0.5591	0.171*
C13	0.5493 (5)	0.8802 (6)	0.6648 (4)	0.132 (2)
C14	0.52449 (19)	0.7162 (4)	0.7069 (2)	0.0638 (8)
C15	0.5482 (3)	0.5519 (5)	0.6653 (3)	0.0804 (11)
C16	0.5931 (3)	0.5577 (5)	0.5851 (3)	0.0820 (11)
H16	0.607 (3)	0.436 (7)	0.554 (3)	0.119 (15)*
H3	0.536 (3)	0.978 (7)	0.692 (3)	0.105 (14)*
H15	0.532 (3)	0.429 (7)	0.688 (3)	0.116 (15)*
H1	0.664 (5)	0.724 (9)	0.435 (5)	0.19 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0775 (14)	0.0375 (10)	0.1079 (19)	0.0042 (10)	−0.0002 (13)	−0.0057 (11)
O2	0.0619 (11)	0.0375 (9)	0.0732 (13)	0.0048 (8)	0.0123 (9)	0.0034 (9)
N1	0.0574 (13)	0.0649 (15)	0.0460 (13)	−0.0109 (12)	−0.0022 (10)	0.0099 (11)
N2	0.0775 (19)	0.0689 (18)	0.111 (2)	−0.0070 (15)	0.0197 (17)	−0.0305 (18)
C1	0.0587 (16)	0.0366 (13)	0.077 (2)	−0.0038 (12)	−0.0134 (14)	−0.0020 (14)
C2	0.085 (2)	0.0346 (13)	0.078 (2)	−0.0131 (14)	−0.0196 (17)	0.0110 (15)
C3	0.081 (2)	0.0536 (17)	0.0642 (19)	−0.0229 (16)	−0.0134 (16)	0.0129 (16)
C4	0.0552 (15)	0.0543 (15)	0.0545 (16)	−0.0139 (12)	−0.0079 (12)	0.0117 (13)
C5	0.0512 (14)	0.0429 (13)	0.0539 (16)	−0.0038 (11)	−0.0035 (12)	0.0082 (12)
C6	0.0485 (13)	0.0379 (12)	0.0610 (16)	−0.0056 (11)	−0.0064 (12)	0.0054 (12)
C7	0.0604 (17)	0.0628 (18)	0.0554 (18)	−0.0144 (14)	−0.0016 (13)	0.0085 (15)
C8	0.0587 (15)	0.0592 (16)	0.0452 (15)	−0.0102 (13)	−0.0045 (12)	0.0128 (13)
C9	0.0560 (14)	0.0604 (16)	0.0409 (14)	−0.0168 (13)	−0.0032 (11)	0.0086 (13)
C10	0.0610 (16)	0.0611 (17)	0.0432 (15)	−0.0132 (13)	−0.0061 (12)	0.0150 (13)
C11	0.084 (2)	0.0381 (14)	0.073 (2)	0.0052 (14)	0.0228 (18)	0.0067 (14)
C12	0.210 (6)	0.058 (2)	0.187 (5)	−0.038 (3)	0.134 (5)	−0.027 (3)
C13	0.178 (5)	0.047 (2)	0.197 (6)	−0.031 (3)	0.124 (5)	−0.027 (3)
C14	0.0371 (13)	0.0482 (15)	0.105 (2)	−0.0023 (11)	0.0029 (13)	−0.0023 (15)
C15	0.085 (2)	0.0499 (19)	0.104 (3)	0.0189 (17)	0.001 (2)	−0.0020 (19)
C16	0.079 (2)	0.058 (2)	0.104 (3)	0.0165 (17)	−0.007 (2)	−0.008 (2)

Geometric parameters (Å, º)

O1—C1	1.361 (4)	C4—C7	1.468 (4)
O2—C6	1.379 (3)	C5—C6	1.373 (4)
O2—C11	1.420 (3)	C8—C10^i	1.383 (4)
N1—C7	1.273 (4)	C8—C9	1.399 (4)
N1—C9	1.414 (4)	C9—C10	1.392 (4)
N2—C12	1.321 (5)	C10—C8^i	1.383 (4)
N2—C16	1.330 (5)	C12—C13	1.370 (7)
C1—C2	1.382 (5)	C13—C14	1.366 (5)
C1—C6	1.411 (4)	C14—C15	1.361 (4)
C2—C3	1.380 (5)	C14—C14^ii	1.485 (7)
C3—C4	1.394 (4)	C15—C16	1.377 (6)
C4—C5	1.399 (4)
C6—O2—C11	116.6 (2)	O2—C6—C1	113.7 (3)
C7—N1—C9	118.6 (3)	N1—C7—C4	122.9 (3)
C12—N2—C16	113.5 (4)	C10^i—C8—C9	120.5 (3)
O1—C1—C2	119.6 (3)	C10—C9—C8	117.9 (3)
O1—C1—C6	121.8 (3)	C10—C9—N1	118.7 (2)
C2—C1—C6	118.6 (3)	C8—C9—N1	123.4 (3)
C3—C2—C1	120.7 (3)	C8^i—C10—C9	121.6 (3)
C2—C3—C4	120.6 (3)	N2—C12—C13	125.4 (4)
C3—C4—C5	119.2 (3)	C14—C13—C12	120.1 (4)
C3—C4—C7	119.3 (3)	C15—C14—C13	115.9 (4)
C5—C4—C7	121.5 (3)	C15—C14—C14^ii	121.8 (2)
C6—C5—C4	119.9 (3)	C13—C14—C14^ii	122.3 (2)
C5—C6—O2	125.4 (2)	C14—C15—C16	120.1 (4)
C5—C6—C1	120.9 (3)	N2—C16—C15	125.0 (4)
O1—C1—C2—C3	−177.2 (3)	C3—C4—C7—N1	−169.7 (3)
C6—C1—C2—C3	1.9 (4)	C5—C4—C7—N1	7.4 (4)
C1—C2—C3—C4	0.1 (4)	C10^i—C8—C9—C10	−0.7 (4)
C2—C3—C4—C5	−2.0 (4)	C10^i—C8—C9—N1	−178.2 (2)
C2—C3—C4—C7	175.2 (3)	C7—N1—C9—C10	143.8 (3)
C3—C4—C5—C6	1.9 (4)	C7—N1—C9—C8	−38.8 (4)
C7—C4—C5—C6	−175.2 (2)	C8—C9—C10—C8^i	0.7 (4)
C4—C5—C6—O2	−179.1 (2)	N1—C9—C10—C8^i	178.3 (2)
C4—C5—C6—C1	0.1 (4)	C16—N2—C12—C13	−0.5 (9)
C11—O2—C6—C5	−0.1 (4)	N2—C12—C13—C14	0.8 (11)
C11—O2—C6—C1	−179.4 (3)	C12—C13—C14—C15	0.0 (8)
O1—C1—C6—C5	177.1 (2)	C12—C13—C14—C14^ii	179.5 (5)
C2—C1—C6—C5	−2.0 (4)	C13—C14—C15—C16	−0.9 (6)
O1—C1—C6—O2	−3.6 (3)	C14^ii—C14—C15—C16	179.7 (4)
C2—C1—C6—O2	177.3 (2)	C12—N2—C16—C15	−0.4 (6)
C9—N1—C7—C4	175.1 (2)	C14—C15—C16—N2	1.2 (6)

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