Download citation
Download citation
link to html
The creation of ternary multi-component crystals through the introduction of 18-crown-6 to direct the hydrogen-bonding motifs of the other molecular components was investigated for 3,5-dinitrobenzoic acid (3,5-dnba) with 4-aminobenzoic acid (4-aba). The creation of a binary complex between 18-crown-6 and 4-aba (C12H24O6·2C7H7NO2)2 and a ternary salt between 3,5-dnba, 18-crown-6 and 4-aba (C12H24O6·C7H8NO2+·C7H3N2O6·C7H4N2O6) were confirmed by single-crystal structure determination. In both structures, the amino molecules bind to the crown ether through N—H...O hydrogen bonds, leaving available only a single O atom site on the crown with restricted geometry to potentially accept a hydrogen bond from 3,5-dnba. While 3,5-dnba and 4-aba form a binary co-crystal containing neutral molecules, the shape-selective nature of 18-crown-6 preferentially binds protonated amino molecules, thereby leading to the formation of the ternary salt, despite the predicted low concentration of the protonated species in the crystallizing solution. Thus, through the choice of crown ether it may be possible to control both location and nature of the available bonding sites for the designed creation of ternary crystals.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520613026036/bi5005sup1.cif
Contains datablocks 1, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613026036/bi50051sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613026036/bi50052sup3.hkl
Contains datablock 2

CCDC references: 962492; 962493

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: CrystalMaker (Palmer, 2005) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2013.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
(1) 18-crown-6/bis(4-aminobenzoic acid) top
Crystal data top
C12H24O6·2(C7H7NO2)F(000) = 3456
Mr = 538.58Dx = 1.245 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.3947 (3) ÅCell parameters from 9698 reflections
b = 17.5546 (5) Åθ = 2.3–23.3°
c = 47.2700 (14) ŵ = 0.10 mm1
β = 91.321 (2)°T = 173 K
V = 8623.3 (4) Å3Block, colourless
Z = 120.79 × 0.65 × 0.53 mm
Data collection top
Bruker APEX-II CCD
diffractometer
10452 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
φ and ω scansθmax = 26.1°, θmin = 1.7°
Absorption correction: multi-scan
SADABS (Bruker, 2008)
h = 1211
Tmin = 0.928, Tmax = 0.950k = 2021
132140 measured reflectionsl = 5852
16030 independent reflections
Refinement top
Refinement on F26 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.073H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.199 w = 1/[σ2(Fo2) + (0.0614P)2 + 16.5586P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
16030 reflectionsΔρmax = 0.91 e Å3
1114 parametersΔρmin = 0.37 e Å3
Crystal data top
C12H24O6·2(C7H7NO2)V = 8623.3 (4) Å3
Mr = 538.58Z = 12
Monoclinic, P21/nMo Kα radiation
a = 10.3947 (3) ŵ = 0.10 mm1
b = 17.5546 (5) ÅT = 173 K
c = 47.2700 (14) Å0.79 × 0.65 × 0.53 mm
β = 91.321 (2)°
Data collection top
Bruker APEX-II CCD
diffractometer
16030 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2008)
10452 reflections with I > 2σ(I)
Tmin = 0.928, Tmax = 0.950Rint = 0.045
132140 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0736 restraints
wR(F2) = 0.199H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0614P)2 + 16.5586P]
where P = (Fo2 + 2Fc2)/3
16030 reflectionsΔρmax = 0.91 e Å3
1114 parametersΔρmin = 0.37 e Å3
Special details top

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. One section of one crown ether is refined as disordered over two positions.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A0.7184 (3)0.32762 (18)0.01502 (6)0.0626 (8)
O2AA0.4540 (6)0.3599 (4)0.02787 (16)0.0631 (18)0.673 (12)
O2AB0.4614 (8)0.3883 (6)0.0153 (2)0.033 (3)0.327 (12)
O3A0.2490 (3)0.26694 (15)0.00704 (6)0.0495 (7)
O4A0.3506 (2)0.16745 (14)0.03292 (5)0.0430 (6)
O5A0.5925 (2)0.11338 (14)0.04352 (5)0.0413 (6)
O6A0.7895 (2)0.18617 (15)0.00732 (5)0.0421 (6)
C1A0.8751 (4)0.2487 (3)0.00409 (8)0.0508 (11)
H1AA0.87060.28110.02120.061*
H1AB0.96440.22990.00170.061*
C2A0.8391 (4)0.2939 (3)0.02100 (9)0.0524 (11)
H2AA0.83390.26050.03780.063*
H2AB0.90450.33370.02500.063*
C3A0.6734 (5)0.3715 (3)0.03805 (11)0.0754 (15)
H3AA0.74150.40660.04510.090*0.673 (12)
H3AB0.64860.33770.05380.090*0.673 (12)
H3AC0.68790.42620.03420.090*0.327 (12)
H3AD0.72350.35800.05540.090*0.327 (12)
C4AA0.5612 (7)0.4147 (4)0.02741 (15)0.062 (2)0.673 (12)
H4AA0.57520.43320.00790.075*0.673 (12)
H4AB0.54400.45890.03980.075*0.673 (12)
C4AB0.5076 (16)0.3562 (9)0.0440 (4)0.062 (5)0.327 (12)
H4AC0.48610.30160.04630.075*0.327 (12)
H4AD0.47580.38600.06020.075*0.327 (12)
C5A0.3350 (6)0.3925 (4)0.01860 (15)0.098 (2)
H5AA0.33770.40600.00170.118*0.673 (12)
H5AB0.31610.43900.02960.118*0.673 (12)
H5AC0.30310.42000.00150.118*0.327 (12)
H5AD0.32500.42850.03450.118*0.327 (12)
C6A0.2381 (4)0.3344 (3)0.02331 (10)0.0595 (12)
H6AA0.24170.32030.04360.071*
H6AB0.15240.35700.01930.071*
C7A0.2310 (4)0.2783 (2)0.02255 (9)0.0513 (11)
H7AA0.30180.30990.02980.062*
H7AB0.14890.30530.02630.062*
C8A0.2290 (4)0.2028 (2)0.03715 (8)0.0478 (10)
H8AA0.16050.17030.02930.057*
H8AB0.21090.20980.05760.057*
C9A0.3656 (4)0.0992 (2)0.04863 (9)0.0491 (10)
H9AA0.36790.11090.06910.059*
H9AB0.29230.06460.04540.059*
C10A0.4888 (4)0.0621 (2)0.03917 (9)0.0488 (10)
H10A0.48490.04860.01890.059*
H10B0.50220.01470.05010.059*
C11A0.7140 (4)0.0823 (3)0.03506 (8)0.0526 (11)
H11A0.74180.04430.04920.063*
H11B0.70680.05630.01660.063*
C12A0.8108 (4)0.1449 (3)0.03271 (8)0.0508 (11)
H12A0.89890.12330.03230.061*
H12B0.80220.17930.04920.061*
O1B0.0630 (3)0.08359 (15)0.01362 (6)0.0453 (7)
H1B0.067 (5)0.053 (3)0.0051 (12)0.108 (19)*
O2B0.0586 (3)0.00576 (15)0.03328 (6)0.0542 (7)
C1B0.0039 (3)0.0566 (2)0.03489 (8)0.0366 (8)
C2B0.0107 (3)0.09804 (19)0.06156 (7)0.0325 (8)
C3B0.0349 (4)0.0665 (2)0.08643 (8)0.0428 (9)
H3B0.07530.01800.08560.051*
C4B0.0236 (4)0.1030 (2)0.11202 (8)0.0416 (9)
H4B0.05430.07940.12860.050*
C5B0.0334 (3)0.1756 (2)0.11355 (7)0.0350 (8)
C6B0.0779 (3)0.2083 (2)0.08843 (7)0.0357 (8)
H6B0.11560.25760.08900.043*
C7B0.0676 (3)0.17028 (19)0.06311 (7)0.0333 (8)
H7B0.09950.19320.04650.040*
N1B0.0484 (4)0.2125 (2)0.13838 (8)0.0469 (9)
H1BA0.008 (4)0.198 (3)0.1528 (10)0.066 (15)*
H1BB0.080 (5)0.258 (3)0.1378 (11)0.082 (18)*
O1C0.5843 (3)0.48121 (14)0.13538 (5)0.0444 (7)
H1C0.596 (5)0.459 (3)0.1550 (11)0.098 (17)*
O2C0.6327 (3)0.59009 (15)0.15738 (5)0.0460 (7)
C1C0.5960 (3)0.5554 (2)0.13580 (7)0.0321 (8)
C2C0.5595 (3)0.59509 (19)0.10972 (7)0.0284 (7)
C3C0.5677 (3)0.67427 (19)0.10832 (7)0.0330 (8)
H3C0.60210.70180.12410.040*
C4C0.5268 (3)0.7131 (2)0.08465 (7)0.0342 (8)
H4C0.53470.76690.08410.041*
C5C0.4735 (3)0.6747 (2)0.06118 (7)0.0339 (8)
C6C0.4685 (4)0.5952 (2)0.06250 (7)0.0407 (9)
H6C0.43530.56740.04670.049*
C7C0.5108 (4)0.5566 (2)0.08624 (7)0.0376 (8)
H7C0.50650.50260.08650.045*
N1C0.4246 (4)0.7134 (3)0.03864 (8)0.0468 (9)
H1CA0.436 (4)0.760 (3)0.0390 (9)0.055 (14)*
H1CB0.403 (5)0.690 (3)0.0245 (11)0.077 (18)*
O1D0.5960 (2)0.53383 (14)0.20783 (5)0.0424 (6)
H1D0.61340.54890.19150.064*
O2D0.5878 (3)0.42146 (14)0.18572 (5)0.0418 (6)
C1D0.5725 (3)0.4601 (2)0.20724 (7)0.0316 (8)
C2D0.5276 (3)0.42663 (19)0.23337 (7)0.0289 (7)
C3D0.5112 (3)0.4690 (2)0.25803 (7)0.0332 (8)
H3D0.53140.52170.25810.040*
C4D0.4665 (3)0.4358 (2)0.28221 (7)0.0365 (8)
H4D0.45770.46570.29880.044*
C5D0.4336 (3)0.3580 (2)0.28263 (7)0.0318 (8)
C6D0.4501 (3)0.3159 (2)0.25777 (7)0.0343 (8)
H6D0.42930.26320.25760.041*
C7D0.4956 (3)0.34900 (19)0.23380 (7)0.0318 (8)
H7D0.50560.31910.21720.038*
N1D0.3863 (3)0.3245 (2)0.30573 (8)0.0457 (8)
H1DA0.380 (5)0.348 (3)0.3214 (11)0.078 (17)*
H1DB0.380 (4)0.275 (3)0.3063 (10)0.069 (16)*
O1E0.1113 (2)0.54213 (16)0.02265 (5)0.0458 (7)
H1E0.098 (6)0.515 (4)0.0013 (14)0.13 (2)*
O2E0.1001 (2)0.52463 (16)0.02695 (5)0.0447 (6)
C1E0.0067 (3)0.55030 (19)0.03627 (7)0.0318 (8)
C2E0.0144 (3)0.59040 (18)0.06338 (6)0.0286 (7)
C3E0.0943 (3)0.60271 (19)0.07964 (7)0.0304 (7)
H3E0.17600.58590.07270.036*
C4E0.0853 (3)0.63853 (19)0.10529 (7)0.0317 (8)
H4E0.16070.64640.11590.038*
C5E0.0348 (3)0.66386 (19)0.11615 (7)0.0328 (8)
C6E0.1436 (3)0.6526 (2)0.09947 (7)0.0351 (8)
H6E0.22520.67030.10610.042*
C7E0.1332 (3)0.6166 (2)0.07391 (7)0.0334 (8)
H7E0.20810.60910.06310.040*
N1E0.0442 (4)0.6984 (2)0.14163 (7)0.0463 (9)
H1EA0.023 (4)0.709 (2)0.1523 (8)0.043 (11)*
H1EB0.119 (4)0.712 (2)0.1450 (9)0.053 (14)*
O1F0.1069 (3)0.49496 (18)0.30440 (6)0.0562 (8)
H1F0.101 (6)0.513 (4)0.3282 (15)0.15 (3)*
O2F0.1069 (3)0.48524 (16)0.30858 (5)0.0502 (7)
C1F0.0025 (4)0.4764 (2)0.29457 (7)0.0348 (8)
C2F0.0066 (3)0.44390 (19)0.26603 (7)0.0323 (8)
C3F0.1245 (3)0.4240 (2)0.25453 (7)0.0355 (8)
H3F0.20160.43120.26540.043*
C4F0.1302 (3)0.3943 (2)0.22782 (7)0.0370 (8)
H4F0.21130.38090.22040.044*
C5F0.0181 (3)0.38328 (19)0.21126 (7)0.0324 (8)
C6F0.1004 (3)0.4017 (2)0.22307 (7)0.0358 (8)
H6F0.17780.39340.21250.043*
C7F0.1055 (3)0.4316 (2)0.24980 (7)0.0355 (8)
H7F0.18650.44410.25740.043*
N1F0.0247 (4)0.3561 (2)0.18454 (7)0.0485 (9)
H1FA0.100 (4)0.343 (2)0.1789 (8)0.049 (12)*
H1FB0.043 (5)0.343 (3)0.1779 (11)0.09 (2)*
O1G0.1069 (3)0.54242 (16)0.35941 (5)0.0468 (7)
H1G0.104 (7)0.514 (4)0.3351 (15)0.15 (3)*
O2G0.1076 (3)0.54402 (18)0.35628 (5)0.0544 (8)
C1G0.0024 (4)0.5568 (2)0.36977 (7)0.0360 (8)
C2G0.0075 (3)0.58889 (19)0.39831 (7)0.0324 (8)
C3G0.1047 (3)0.6076 (2)0.41375 (7)0.0371 (8)
H3G0.18620.59980.40550.044*
C4G0.0983 (3)0.6367 (2)0.44044 (7)0.0380 (9)
H4G0.17560.64930.45050.046*
C5G0.0206 (3)0.6485 (2)0.45334 (7)0.0333 (8)
C6G0.1334 (3)0.6301 (2)0.43786 (7)0.0369 (8)
H6G0.21500.63750.44610.044*
C7G0.1259 (4)0.6015 (2)0.41087 (7)0.0381 (8)
H7G0.20290.59000.40050.046*
N1G0.0261 (4)0.6741 (2)0.48016 (7)0.0463 (9)
H1GA0.097 (4)0.684 (2)0.4871 (8)0.034 (10)*
H1GB0.040 (5)0.690 (3)0.4882 (10)0.064 (15)*
O1H0.1057 (2)0.69527 (14)0.19681 (5)0.0429 (6)
O2H0.2243 (3)0.79586 (16)0.16004 (6)0.0548 (7)
O3H0.0290 (3)0.88757 (17)0.12848 (6)0.0530 (7)
O4H0.2292 (3)0.8539 (2)0.13866 (6)0.0755 (11)
O5H0.3219 (2)0.72479 (15)0.16639 (5)0.0454 (6)
O6H0.1463 (2)0.64817 (14)0.20415 (6)0.0463 (7)
C1H0.0434 (4)0.5947 (2)0.20215 (10)0.0545 (11)
H1HA0.06570.54850.21320.065*
H1HB0.02900.57940.18220.065*
C2H0.0766 (4)0.6299 (2)0.21331 (9)0.0511 (10)
H2HA0.14860.59310.21200.061*
H2HB0.06310.64440.23340.061*
C3H0.2276 (4)0.7264 (3)0.20270 (8)0.0494 (10)
H3HA0.23740.73090.22340.059*
H3HB0.29630.69240.19520.059*
C4H0.2397 (4)0.8021 (2)0.18945 (9)0.0524 (11)
H4HA0.32540.82390.19330.063*
H4HB0.17340.83680.19760.063*
C5H0.2384 (5)0.8670 (3)0.14570 (13)0.0830 (18)
H5HA0.21310.90900.15870.100*
H5HB0.32970.87450.14000.100*
C6H0.1588 (5)0.8691 (3)0.12079 (11)0.0767 (16)
H6HA0.16150.81880.11130.092*
H6HB0.19320.90760.10730.092*
C7H0.0563 (5)0.8736 (3)0.10630 (9)0.0643 (13)
H7HA0.02770.90190.08920.077*
H7HB0.05670.81860.10170.077*
C8H0.1855 (5)0.8980 (4)0.11489 (10)0.0795 (17)
H8HA0.24480.89110.09900.095*
H8HB0.18460.95260.12000.095*
C9H0.3578 (4)0.8338 (3)0.13787 (9)0.0537 (11)
H9HA0.41120.88010.13600.064*
H9HB0.37250.80090.12130.064*
C10H0.3955 (4)0.7924 (2)0.16425 (10)0.0534 (11)
H10C0.48820.77960.16400.064*
H10D0.38060.82530.18090.064*
C11H0.3578 (4)0.6813 (3)0.19072 (10)0.0583 (12)
H11C0.35890.71430.20770.070*
H11D0.44530.66010.18850.070*
C12H0.2637 (4)0.6181 (3)0.19429 (11)0.0608 (12)
H12C0.24840.59190.17600.073*
H12D0.29870.58040.20800.073*
O1I0.2089 (3)0.32047 (18)0.14245 (6)0.0626 (8)
O2I0.0163 (3)0.38849 (18)0.11605 (6)0.0677 (9)
O3I0.2408 (3)0.3445 (2)0.14116 (7)0.0704 (9)
O4I0.2851 (3)0.2409 (2)0.18463 (7)0.0709 (9)
O5I0.0579 (3)0.15949 (18)0.20840 (6)0.0659 (9)
O6I0.1647 (3)0.21133 (19)0.18431 (7)0.0673 (9)
C1I0.2873 (4)0.2230 (3)0.17292 (11)0.0690 (14)
H1IA0.33310.26140.18420.083*
H1IB0.33680.17490.17330.083*
C2I0.2769 (4)0.2496 (3)0.14368 (10)0.0597 (12)
H2IA0.23120.21080.13250.072*
H2IB0.36410.25610.13520.072*
C3I0.2031 (5)0.3491 (3)0.11502 (10)0.0699 (14)
H3IA0.28970.36600.10850.084*
H3IB0.17350.30880.10200.084*
C4I0.1133 (5)0.4137 (3)0.11480 (10)0.0666 (13)
H4IA0.12830.44380.09730.080*
H4IB0.12960.44710.13120.080*
C5I0.1040 (6)0.4438 (3)0.12364 (11)0.0807 (16)
H5IA0.08450.46370.14270.097*
H5IB0.09860.48660.11000.097*
C6I0.2382 (5)0.4103 (3)0.12387 (12)0.0797 (16)
H6IA0.26230.39670.10440.096*
H6IB0.30090.44810.13130.096*
C7I0.3624 (5)0.3160 (4)0.14617 (13)0.0912 (19)
H7IA0.41090.35030.15920.109*
H7IB0.40920.31300.12820.109*
C8I0.3523 (4)0.2362 (3)0.15938 (11)0.0705 (14)
H8IA0.30680.20150.14600.085*
H8IB0.43960.21550.16320.085*
C9I0.2810 (5)0.1706 (3)0.19820 (13)0.0807 (16)
H9IA0.36740.15830.20620.097*
H9IB0.25720.13060.18430.097*
C10I0.1863 (5)0.1709 (3)0.22133 (11)0.0732 (14)
H10E0.20610.12950.23500.088*
H10F0.18980.22000.23160.088*
C11I0.0367 (5)0.1843 (3)0.22582 (9)0.0655 (13)
H11E0.02400.23890.23030.079*
H11F0.03370.15520.24380.079*
C12I0.1633 (5)0.1728 (3)0.21100 (9)0.0673 (13)
H12E0.17850.11770.20800.081*
H12F0.23300.19280.22280.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0495 (18)0.072 (2)0.0654 (19)0.0156 (16)0.0255 (15)0.0180 (16)
O2AA0.064 (4)0.050 (4)0.074 (5)0.017 (3)0.030 (3)0.004 (3)
O2AB0.020 (5)0.035 (6)0.043 (6)0.016 (4)0.002 (4)0.005 (4)
O3A0.0503 (17)0.0474 (16)0.0510 (16)0.0024 (13)0.0043 (13)0.0105 (13)
O4A0.0350 (14)0.0438 (15)0.0501 (15)0.0017 (12)0.0043 (12)0.0008 (12)
O5A0.0420 (15)0.0454 (15)0.0363 (13)0.0080 (12)0.0007 (11)0.0040 (11)
O6A0.0333 (14)0.0577 (17)0.0355 (14)0.0024 (12)0.0039 (11)0.0058 (12)
C1A0.035 (2)0.069 (3)0.048 (2)0.003 (2)0.0021 (18)0.017 (2)
C2A0.039 (2)0.059 (3)0.058 (3)0.008 (2)0.016 (2)0.010 (2)
C3A0.067 (3)0.079 (4)0.079 (3)0.010 (3)0.032 (3)0.035 (3)
C4AA0.071 (5)0.055 (4)0.061 (4)0.010 (3)0.009 (4)0.021 (3)
C4AB0.072 (11)0.059 (9)0.055 (8)0.034 (8)0.003 (6)0.004 (6)
C5A0.078 (4)0.086 (4)0.131 (5)0.001 (3)0.019 (4)0.031 (4)
C6A0.052 (3)0.059 (3)0.069 (3)0.008 (2)0.015 (2)0.001 (2)
C7A0.038 (2)0.058 (3)0.059 (3)0.0141 (19)0.0140 (19)0.022 (2)
C8A0.032 (2)0.070 (3)0.041 (2)0.005 (2)0.0011 (17)0.013 (2)
C9A0.052 (2)0.047 (2)0.048 (2)0.008 (2)0.0042 (19)0.0027 (19)
C10A0.057 (3)0.039 (2)0.051 (2)0.003 (2)0.001 (2)0.0011 (18)
C11A0.056 (3)0.061 (3)0.041 (2)0.024 (2)0.0021 (19)0.001 (2)
C12A0.041 (2)0.075 (3)0.036 (2)0.017 (2)0.0073 (17)0.007 (2)
O1B0.0568 (17)0.0402 (15)0.0389 (15)0.0042 (13)0.0045 (13)0.0062 (12)
O2B0.0656 (19)0.0399 (16)0.0577 (18)0.0170 (14)0.0147 (14)0.0182 (13)
C1B0.0314 (19)0.032 (2)0.047 (2)0.0008 (16)0.0030 (16)0.0071 (17)
C2B0.0271 (18)0.0298 (18)0.040 (2)0.0028 (15)0.0010 (15)0.0085 (15)
C3B0.044 (2)0.033 (2)0.053 (2)0.0052 (17)0.0134 (18)0.0092 (17)
C4B0.043 (2)0.038 (2)0.045 (2)0.0027 (17)0.0156 (17)0.0053 (17)
C5B0.0236 (18)0.041 (2)0.041 (2)0.0041 (15)0.0045 (15)0.0087 (17)
C6B0.0302 (19)0.0326 (19)0.044 (2)0.0025 (15)0.0017 (16)0.0081 (16)
C7B0.0263 (18)0.0336 (19)0.040 (2)0.0044 (15)0.0016 (15)0.0019 (16)
N1B0.048 (2)0.052 (2)0.041 (2)0.0063 (18)0.0042 (16)0.0120 (17)
O1C0.0718 (19)0.0329 (15)0.0282 (13)0.0018 (13)0.0024 (12)0.0086 (11)
O2C0.0631 (18)0.0458 (15)0.0286 (13)0.0165 (13)0.0076 (12)0.0062 (12)
C1C0.0327 (19)0.034 (2)0.0294 (18)0.0024 (15)0.0020 (15)0.0055 (15)
C2C0.0251 (17)0.0336 (19)0.0266 (17)0.0013 (14)0.0012 (13)0.0048 (14)
C3C0.040 (2)0.036 (2)0.0234 (16)0.0047 (16)0.0040 (14)0.0014 (15)
C4C0.042 (2)0.0324 (19)0.0290 (18)0.0010 (16)0.0093 (15)0.0047 (15)
C5C0.0247 (18)0.045 (2)0.0317 (18)0.0019 (16)0.0022 (14)0.0145 (16)
C6C0.051 (2)0.043 (2)0.0276 (18)0.0117 (18)0.0093 (16)0.0026 (16)
C7C0.050 (2)0.0320 (19)0.0305 (18)0.0075 (17)0.0033 (16)0.0055 (15)
N1C0.050 (2)0.049 (2)0.041 (2)0.0048 (18)0.0130 (16)0.0170 (18)
O1D0.0579 (17)0.0352 (14)0.0340 (13)0.0119 (12)0.0008 (12)0.0104 (11)
O2D0.0603 (17)0.0389 (14)0.0264 (13)0.0006 (12)0.0051 (11)0.0069 (11)
C1D0.0299 (19)0.036 (2)0.0289 (18)0.0012 (15)0.0033 (14)0.0055 (15)
C2D0.0247 (17)0.0312 (18)0.0308 (17)0.0007 (14)0.0034 (14)0.0045 (14)
C3D0.037 (2)0.0284 (18)0.0338 (18)0.0017 (15)0.0011 (15)0.0024 (15)
C4D0.040 (2)0.040 (2)0.0298 (18)0.0021 (17)0.0053 (15)0.0016 (16)
C5D0.0246 (17)0.041 (2)0.0302 (18)0.0025 (15)0.0013 (14)0.0106 (15)
C6D0.037 (2)0.0316 (19)0.0345 (19)0.0003 (15)0.0003 (15)0.0062 (15)
C7D0.0370 (19)0.0321 (19)0.0261 (17)0.0011 (15)0.0034 (14)0.0022 (14)
N1D0.054 (2)0.047 (2)0.037 (2)0.0023 (17)0.0142 (16)0.0094 (17)
O1E0.0412 (15)0.0623 (18)0.0344 (14)0.0041 (13)0.0091 (12)0.0168 (13)
O2E0.0359 (15)0.0607 (17)0.0374 (14)0.0031 (13)0.0043 (11)0.0180 (13)
C1E0.033 (2)0.0341 (19)0.0281 (17)0.0008 (16)0.0010 (15)0.0002 (15)
C2E0.0338 (19)0.0297 (18)0.0223 (16)0.0026 (15)0.0008 (14)0.0004 (13)
C3E0.0291 (18)0.0358 (19)0.0262 (17)0.0000 (15)0.0020 (14)0.0012 (14)
C4E0.0293 (18)0.0375 (19)0.0283 (17)0.0024 (15)0.0039 (14)0.0027 (15)
C5E0.037 (2)0.0329 (19)0.0285 (17)0.0016 (16)0.0008 (15)0.0037 (15)
C6E0.0273 (18)0.043 (2)0.0352 (19)0.0057 (16)0.0002 (15)0.0052 (16)
C7E0.0293 (19)0.042 (2)0.0290 (17)0.0006 (16)0.0038 (14)0.0044 (15)
N1E0.042 (2)0.065 (2)0.0324 (18)0.0076 (18)0.0046 (16)0.0193 (16)
O1F0.0522 (18)0.079 (2)0.0379 (15)0.0014 (15)0.0062 (13)0.0198 (15)
O2F0.0548 (17)0.0621 (18)0.0330 (14)0.0022 (14)0.0132 (13)0.0123 (13)
C1F0.042 (2)0.0348 (19)0.0271 (17)0.0008 (16)0.0003 (17)0.0030 (15)
C2F0.039 (2)0.0308 (18)0.0271 (17)0.0001 (15)0.0039 (15)0.0005 (14)
C3F0.034 (2)0.036 (2)0.0358 (19)0.0029 (16)0.0058 (15)0.0050 (16)
C4F0.0306 (19)0.040 (2)0.041 (2)0.0031 (16)0.0005 (16)0.0091 (16)
C5F0.039 (2)0.0285 (18)0.0294 (18)0.0011 (15)0.0007 (15)0.0048 (14)
C6F0.0340 (19)0.041 (2)0.0316 (18)0.0026 (16)0.0080 (15)0.0051 (16)
C7F0.0293 (19)0.042 (2)0.0348 (19)0.0047 (16)0.0005 (15)0.0052 (16)
N1F0.044 (2)0.061 (2)0.0398 (19)0.0006 (19)0.0009 (17)0.0208 (17)
O1G0.0461 (16)0.0592 (18)0.0353 (14)0.0002 (13)0.0052 (12)0.0135 (13)
O2G0.0466 (17)0.080 (2)0.0364 (14)0.0013 (15)0.0072 (13)0.0203 (14)
C1G0.043 (2)0.0334 (19)0.0318 (18)0.0010 (17)0.0004 (17)0.0017 (15)
C2G0.039 (2)0.0335 (19)0.0243 (17)0.0022 (16)0.0018 (15)0.0025 (14)
C3G0.035 (2)0.044 (2)0.0320 (19)0.0098 (17)0.0065 (15)0.0057 (16)
C4G0.034 (2)0.049 (2)0.0311 (18)0.0135 (17)0.0043 (15)0.0073 (16)
C5G0.041 (2)0.0348 (19)0.0242 (17)0.0056 (16)0.0034 (15)0.0034 (14)
C6G0.0315 (19)0.044 (2)0.0349 (19)0.0001 (16)0.0028 (15)0.0022 (16)
C7G0.037 (2)0.044 (2)0.0325 (19)0.0007 (17)0.0066 (16)0.0057 (16)
N1G0.037 (2)0.071 (2)0.0310 (17)0.0098 (19)0.0032 (16)0.0155 (16)
O1H0.0408 (15)0.0398 (15)0.0484 (15)0.0002 (12)0.0058 (12)0.0000 (12)
O2H0.0527 (17)0.0445 (16)0.0677 (19)0.0019 (13)0.0107 (14)0.0114 (14)
O3H0.0409 (16)0.0590 (18)0.0587 (18)0.0032 (13)0.0049 (13)0.0117 (14)
O4H0.0466 (18)0.129 (3)0.0521 (18)0.0261 (19)0.0174 (14)0.0319 (19)
O5H0.0363 (14)0.0512 (16)0.0485 (16)0.0038 (12)0.0006 (12)0.0080 (13)
O6H0.0450 (16)0.0382 (15)0.0556 (16)0.0059 (12)0.0016 (13)0.0025 (12)
C1H0.060 (3)0.035 (2)0.069 (3)0.003 (2)0.008 (2)0.007 (2)
C2H0.055 (3)0.045 (2)0.053 (2)0.011 (2)0.000 (2)0.010 (2)
C3H0.038 (2)0.067 (3)0.043 (2)0.000 (2)0.0035 (18)0.007 (2)
C4H0.034 (2)0.056 (3)0.067 (3)0.0008 (19)0.007 (2)0.018 (2)
C5H0.046 (3)0.068 (3)0.136 (5)0.013 (2)0.020 (3)0.046 (3)
C6H0.062 (3)0.082 (4)0.084 (4)0.009 (3)0.023 (3)0.038 (3)
C7H0.082 (4)0.066 (3)0.045 (2)0.009 (3)0.003 (2)0.010 (2)
C8H0.056 (3)0.126 (5)0.057 (3)0.008 (3)0.008 (2)0.040 (3)
C9H0.039 (2)0.063 (3)0.059 (3)0.003 (2)0.016 (2)0.009 (2)
C10H0.033 (2)0.057 (3)0.070 (3)0.002 (2)0.000 (2)0.007 (2)
C11H0.041 (2)0.066 (3)0.067 (3)0.016 (2)0.005 (2)0.004 (2)
C12H0.059 (3)0.048 (3)0.076 (3)0.018 (2)0.003 (2)0.002 (2)
O1I0.071 (2)0.070 (2)0.0469 (17)0.0249 (17)0.0035 (15)0.0060 (15)
O2I0.091 (3)0.0548 (19)0.0575 (19)0.0080 (18)0.0109 (17)0.0002 (15)
O3I0.059 (2)0.074 (2)0.079 (2)0.0117 (17)0.0122 (17)0.0067 (18)
O4I0.059 (2)0.072 (2)0.081 (2)0.0019 (17)0.0086 (18)0.0071 (19)
O5I0.079 (2)0.063 (2)0.0562 (18)0.0079 (17)0.0019 (17)0.0018 (16)
O6I0.0473 (18)0.080 (2)0.074 (2)0.0013 (16)0.0042 (16)0.0059 (18)
C1I0.043 (3)0.085 (4)0.079 (3)0.001 (2)0.001 (2)0.013 (3)
C2I0.037 (2)0.064 (3)0.078 (3)0.001 (2)0.012 (2)0.011 (3)
C3I0.075 (3)0.081 (4)0.053 (3)0.025 (3)0.008 (2)0.004 (3)
C4I0.072 (3)0.067 (3)0.061 (3)0.017 (3)0.004 (2)0.008 (2)
C5I0.120 (5)0.057 (3)0.066 (3)0.018 (3)0.001 (3)0.007 (3)
C6I0.082 (4)0.064 (3)0.093 (4)0.029 (3)0.011 (3)0.017 (3)
C7I0.051 (3)0.123 (5)0.100 (4)0.022 (3)0.001 (3)0.009 (4)
C8I0.035 (2)0.093 (4)0.084 (4)0.013 (2)0.005 (2)0.006 (3)
C9I0.062 (3)0.077 (4)0.102 (4)0.010 (3)0.014 (3)0.018 (3)
C10I0.079 (4)0.074 (3)0.065 (3)0.004 (3)0.027 (3)0.004 (3)
C11I0.092 (4)0.055 (3)0.050 (3)0.006 (3)0.007 (3)0.005 (2)
C12I0.075 (3)0.073 (3)0.055 (3)0.006 (3)0.022 (2)0.016 (2)
Geometric parameters (Å, º) top
O1A—C2A1.410 (5)O1F—H1F1.17 (7)
O1A—C3A1.421 (5)O2F—C1F1.268 (4)
O2AA—C5A1.422 (8)O2F—H1G1.35 (7)
O2AA—C4AA1.472 (11)C1F—C2F1.466 (5)
O2AB—C5A1.329 (10)C2F—C3F1.396 (5)
O2AB—C4AB1.53 (2)C2F—C7F1.397 (5)
O3A—C6A1.419 (5)C3F—C4F1.369 (5)
O3A—C7A1.420 (5)C3F—H3F0.9500
O4A—C8A1.418 (4)C4F—C5F1.402 (5)
O4A—C9A1.420 (5)C4F—H4F0.9500
O5A—C10A1.423 (5)C5F—N1F1.353 (5)
O5A—C11A1.425 (4)C5F—C6F1.402 (5)
O6A—C1A1.419 (5)C6F—C7F1.370 (5)
O6A—C12A1.424 (5)C6F—H6F0.9500
C1A—C2A1.482 (6)C7F—H7F0.9500
C1A—H1AA0.9900N1F—H1FA0.87 (4)
C1A—H1AB0.9900N1F—H1FB0.80 (6)
C2A—H2AA0.9900O1G—C1G1.274 (4)
C2A—H2AB0.9900O1G—H1G1.25 (7)
C3A—C4AA1.470 (8)O2G—C1G1.273 (4)
C3A—C4AB1.773 (17)O2G—H1F1.44 (7)
C3A—H3AA0.9900C1G—C2G1.464 (5)
C3A—H3AB0.9900C2G—C7G1.396 (5)
C3A—H3AC0.9900C2G—C3G1.400 (5)
C3A—H3AD0.9900C3G—C4G1.365 (5)
C4AA—H4AA0.9900C3G—H3G0.9500
C4AA—H4AB0.9900C4G—C5G1.406 (5)
C4AB—H4AC0.9900C4G—H4G0.9500
C4AB—H4AD0.9900C5G—N1G1.347 (4)
C5A—C6A1.454 (7)C5G—C6G1.405 (5)
C5A—H5AA0.9900C6G—C7G1.375 (5)
C5A—H5AB0.9900C6G—H6G0.9500
C5A—H5AC0.9900C7G—H7G0.9500
C5A—H5AD0.9900N1G—H1GA0.84 (4)
C6A—H6AA0.9900N1G—H1GB0.82 (5)
C6A—H6AB0.9900O1H—C3H1.414 (4)
C7A—C8A1.494 (6)O1H—C2H1.417 (5)
C7A—H7AA0.9900O2H—C4H1.407 (5)
C7A—H7AB0.9900O2H—C5H1.427 (5)
C8A—H8AA0.9900O3H—C7H1.411 (5)
C8A—H8AB0.9900O3H—C6H1.427 (5)
C9A—C10A1.496 (6)O4H—C9H1.383 (5)
C9A—H9AA0.9900O4H—C8H1.429 (5)
C9A—H9AB0.9900O5H—C10H1.417 (5)
C10A—H10A0.9900O5H—C11H1.423 (5)
C10A—H10B0.9900O6H—C12H1.418 (5)
C11A—C12A1.492 (6)O6H—C1H1.425 (5)
C11A—H11A0.9900C1H—C2H1.499 (6)
C11A—H11B0.9900C1H—H1HA0.9900
C12A—H12A0.9900C1H—H1HB0.9900
C12A—H12B0.9900C2H—H2HA0.9900
O1B—C1B1.281 (4)C2H—H2HB0.9900
O1B—H1B1.04 (6)C3H—C4H1.474 (6)
O2B—C1B1.275 (4)C3H—H3HA0.9900
C1B—C2B1.456 (5)C3H—H3HB0.9900
C2B—C3B1.392 (5)C4H—H4HA0.9900
C2B—C7B1.400 (5)C4H—H4HB0.9900
C3B—C4B1.372 (5)C5H—C6H1.455 (7)
C3B—H3B0.9500C5H—H5HA0.9900
C4B—C5B1.406 (5)C5H—H5HB0.9900
C4B—H4B0.9500C6H—H6HA0.9900
C5B—N1B1.346 (5)C6H—H6HB0.9900
C5B—C6B1.407 (5)C7H—C8H1.458 (7)
C6B—C7B1.373 (5)C7H—H7HA0.9900
C6B—H6B0.9500C7H—H7HB0.9900
C7B—H7B0.9500C8H—H8HA0.9900
N1B—H1BA0.85 (5)C8H—H8HB0.9900
N1B—H1BB0.86 (6)C9H—C10H1.488 (6)
O1C—C1C1.308 (4)C9H—H9HA0.9900
O1C—H1C1.01 (5)C9H—H9HB0.9900
O2C—C1C1.241 (4)C10H—H10C0.9900
C1C—C2C1.459 (4)C10H—H10D0.9900
C2C—C7C1.385 (5)C11H—C12H1.492 (6)
C2C—C3C1.394 (5)C11H—H11C0.9900
C3C—C4C1.369 (5)C11H—H11D0.9900
C3C—H3C0.9500C12H—H12C0.9900
C4C—C5C1.400 (5)C12H—H12D0.9900
C4C—H4C0.9500O1I—C3I1.393 (5)
C5C—N1C1.353 (5)O1I—C2I1.433 (5)
C5C—C6C1.398 (5)O2I—C5I1.374 (6)
C6C—C7C1.374 (5)O2I—C4I1.418 (6)
C6C—H6C0.9500O3I—C7I1.375 (6)
C7C—H7C0.9500O3I—C6I1.415 (6)
N1C—H1CA0.83 (5)O4I—C9I1.392 (6)
N1C—H1CB0.81 (5)O4I—C8I1.400 (6)
O1D—C1D1.317 (4)O5I—C11I1.367 (5)
O1D—H1D0.8400O5I—C10I1.469 (6)
O2D—C1D1.236 (4)O6I—C1I1.387 (5)
C1D—C2D1.454 (4)O6I—C12I1.432 (5)
C2D—C3D1.396 (5)C1I—C2I1.465 (7)
C2D—C7D1.403 (5)C1I—H1IA0.9900
C3D—C4D1.373 (5)C1I—H1IB0.9900
C3D—H3D0.9500C2I—H2IA0.9900
C4D—C5D1.409 (5)C2I—H2IB0.9900
C4D—H4D0.9500C3I—C4I1.468 (7)
C5D—N1D1.343 (4)C3I—H3IA0.9900
C5D—C6D1.402 (5)C3I—H3IB0.9900
C6D—C7D1.367 (5)C4I—H4IA0.9900
C6D—H6D0.9500C4I—H4IB0.9900
C7D—H7D0.9500C5I—C6I1.514 (8)
N1D—H1DA0.85 (5)C5I—H5IA0.9900
N1D—H1DB0.86 (5)C5I—H5IB0.9900
O1E—C1E1.285 (4)C6I—H6IA0.9900
O1E—H1E1.12 (6)C6I—H6IB0.9900
O2E—C1E1.267 (4)C7I—C8I1.539 (8)
C1E—C2E1.463 (4)C7I—H7IA0.9900
C2E—C3E1.397 (4)C7I—H7IB0.9900
C2E—C7E1.399 (5)C8I—H8IA0.9900
C3E—C4E1.367 (4)C8I—H8IB0.9900
C3E—H3E0.9500C9I—C10I1.488 (7)
C4E—C5E1.411 (5)C9I—H9IA0.9900
C4E—H4E0.9500C9I—H9IB0.9900
C5E—N1E1.350 (4)C10I—H10E0.9900
C5E—C6E1.407 (5)C10I—H10F0.9900
C6E—C7E1.366 (5)C11I—C12I1.490 (7)
C6E—H6E0.9500C11I—H11E0.9900
C7E—H7E0.9500C11I—H11F0.9900
N1E—H1EA0.89 (4)C12I—H12E0.9900
N1E—H1EB0.82 (4)C12I—H12F0.9900
O1F—C1F1.281 (4)
C2A—O1A—C3A112.4 (3)C3F—C2F—C1F120.0 (3)
C5A—O2AA—C4AA112.7 (6)C7F—C2F—C1F121.6 (3)
C5A—O2AB—C4AB102.0 (10)C4F—C3F—C2F120.8 (3)
C6A—O3A—C7A114.0 (3)C4F—C3F—H3F119.6
C8A—O4A—C9A113.8 (3)C2F—C3F—H3F119.6
C10A—O5A—C11A112.7 (3)C3F—C4F—C5F120.9 (3)
C1A—O6A—C12A112.0 (3)C3F—C4F—H4F119.5
O6A—C1A—C2A109.3 (3)C5F—C4F—H4F119.5
O6A—C1A—H1AA109.8N1F—C5F—C4F120.7 (3)
C2A—C1A—H1AA109.8N1F—C5F—C6F121.1 (3)
O6A—C1A—H1AB109.8C4F—C5F—C6F118.2 (3)
C2A—C1A—H1AB109.8C7F—C6F—C5F120.6 (3)
H1AA—C1A—H1AB108.3C7F—C6F—H6F119.7
O1A—C2A—C1A107.7 (3)C5F—C6F—H6F119.7
O1A—C2A—H2AA110.2C6F—C7F—C2F121.1 (3)
C1A—C2A—H2AA110.2C6F—C7F—H7F119.5
O1A—C2A—H2AB110.2C2F—C7F—H7F119.5
C1A—C2A—H2AB110.2C5F—N1F—H1FA116 (3)
H2AA—C2A—H2AB108.5C5F—N1F—H1FB114 (4)
O1A—C3A—C4AA106.9 (4)H1FA—N1F—H1FB126 (5)
O1A—C3A—C4AB112.2 (6)C1G—O1G—H1G116 (3)
O1A—C3A—H3AA110.4C1G—O2G—H1F118 (3)
C4AA—C3A—H3AA110.4O2G—C1G—O1G122.4 (3)
O1A—C3A—H3AB110.4O2G—C1G—C2G118.7 (3)
C4AA—C3A—H3AB110.4O1G—C1G—C2G118.8 (3)
H3AA—C3A—H3AB108.6C7G—C2G—C3G118.2 (3)
O1A—C3A—H3AC109.2C7G—C2G—C1G120.2 (3)
C4AB—C3A—H3AC109.2C3G—C2G—C1G121.6 (3)
O1A—C3A—H3AD109.2C4G—C3G—C2G120.8 (3)
C4AB—C3A—H3AD109.2C4G—C3G—H3G119.6
H3AC—C3A—H3AD107.9C2G—C3G—H3G119.6
C3A—C4AA—O2AA104.6 (6)C3G—C4G—C5G121.2 (3)
C3A—C4AA—H4AA110.8C3G—C4G—H4G119.4
O2AA—C4AA—H4AA110.8C5G—C4G—H4G119.4
C3A—C4AA—H4AB110.8N1G—C5G—C6G120.9 (3)
O2AA—C4AA—H4AB110.8N1G—C5G—C4G120.9 (3)
H4AA—C4AA—H4AB108.9C6G—C5G—C4G118.1 (3)
O2AB—C4AB—C3A95.2 (9)C7G—C6G—C5G120.2 (3)
O2AB—C4AB—H4AC112.7C7G—C6G—H6G119.9
C3A—C4AB—H4AC112.7C5G—C6G—H6G119.9
O2AB—C4AB—H4AD112.7C6G—C7G—C2G121.5 (3)
C3A—C4AB—H4AD112.7C6G—C7G—H7G119.3
H4AC—C4AB—H4AD110.2C2G—C7G—H7G119.3
O2AB—C5A—C6A132.0 (7)C5G—N1G—H1GA120 (3)
O2AA—C5A—C6A105.7 (6)C5G—N1G—H1GB119 (3)
O2AA—C5A—H5AA110.6H1GA—N1G—H1GB119 (4)
C6A—C5A—H5AA110.6C3H—O1H—C2H112.7 (3)
O2AA—C5A—H5AB110.6C4H—O2H—C5H112.8 (4)
C6A—C5A—H5AB110.6C7H—O3H—C6H112.2 (4)
H5AA—C5A—H5AB108.7C9H—O4H—C8H114.0 (3)
O2AB—C5A—H5AC104.2C10H—O5H—C11H112.1 (3)
C6A—C5A—H5AC104.2C12H—O6H—C1H112.5 (3)
O2AB—C5A—H5AD104.2O6H—C1H—C2H109.5 (3)
C6A—C5A—H5AD104.2O6H—C1H—H1HA109.8
H5AC—C5A—H5AD105.6C2H—C1H—H1HA109.8
O3A—C6A—C5A116.0 (4)O6H—C1H—H1HB109.8
O3A—C6A—H6AA108.3C2H—C1H—H1HB109.8
C5A—C6A—H6AA108.3H1HA—C1H—H1HB108.2
O3A—C6A—H6AB108.3O1H—C2H—C1H108.0 (3)
C5A—C6A—H6AB108.3O1H—C2H—H2HA110.1
H6AA—C6A—H6AB107.4C1H—C2H—H2HA110.1
O3A—C7A—C8A109.3 (3)O1H—C2H—H2HB110.1
O3A—C7A—H7AA109.8C1H—C2H—H2HB110.1
C8A—C7A—H7AA109.8H2HA—C2H—H2HB108.4
O3A—C7A—H7AB109.8O1H—C3H—C4H109.5 (3)
C8A—C7A—H7AB109.8O1H—C3H—H3HA109.8
H7AA—C7A—H7AB108.3C4H—C3H—H3HA109.8
O4A—C8A—C7A108.6 (3)O1H—C3H—H3HB109.8
O4A—C8A—H8AA110.0C4H—C3H—H3HB109.8
C7A—C8A—H8AA110.0H3HA—C3H—H3HB108.2
O4A—C8A—H8AB110.0O2H—C4H—C3H109.8 (3)
C7A—C8A—H8AB110.0O2H—C4H—H4HA109.7
H8AA—C8A—H8AB108.3C3H—C4H—H4HA109.7
O4A—C9A—C10A108.4 (3)O2H—C4H—H4HB109.7
O4A—C9A—H9AA110.0C3H—C4H—H4HB109.7
C10A—C9A—H9AA110.0H4HA—C4H—H4HB108.2
O4A—C9A—H9AB110.0O2H—C5H—C6H110.6 (4)
C10A—C9A—H9AB110.0O2H—C5H—H5HA109.5
H9AA—C9A—H9AB108.4C6H—C5H—H5HA109.5
O5A—C10A—C9A109.1 (3)O2H—C5H—H5HB109.5
O5A—C10A—H10A109.9C6H—C5H—H5HB109.5
C9A—C10A—H10A109.9H5HA—C5H—H5HB108.1
O5A—C10A—H10B109.9O3H—C6H—C5H110.6 (4)
C9A—C10A—H10B109.9O3H—C6H—H6HA109.5
H10A—C10A—H10B108.3C5H—C6H—H6HA109.5
O5A—C11A—C12A109.3 (3)O3H—C6H—H6HB109.5
O5A—C11A—H11A109.8C5H—C6H—H6HB109.5
C12A—C11A—H11A109.8H6HA—C6H—H6HB108.1
O5A—C11A—H11B109.8O3H—C7H—C8H109.4 (4)
C12A—C11A—H11B109.8O3H—C7H—H7HA109.8
H11A—C11A—H11B108.3C8H—C7H—H7HA109.8
O6A—C12A—C11A108.6 (3)O3H—C7H—H7HB109.8
O6A—C12A—H12A110.0C8H—C7H—H7HB109.8
C11A—C12A—H12A110.0H7HA—C7H—H7HB108.2
O6A—C12A—H12B110.0O4H—C8H—C7H109.5 (4)
C11A—C12A—H12B110.0O4H—C8H—H8HA109.8
H12A—C12A—H12B108.3C7H—C8H—H8HA109.8
C1B—O1B—H1B120 (3)O4H—C8H—H8HB109.8
O2B—C1B—O1B121.6 (3)C7H—C8H—H8HB109.8
O2B—C1B—C2B119.7 (3)H8HA—C8H—H8HB108.2
O1B—C1B—C2B118.7 (3)O4H—C9H—C10H109.7 (3)
C3B—C2B—C7B117.9 (3)O4H—C9H—H9HA109.7
C3B—C2B—C1B121.5 (3)C10H—C9H—H9HA109.7
C7B—C2B—C1B120.6 (3)O4H—C9H—H9HB109.7
C4B—C3B—C2B122.4 (3)C10H—C9H—H9HB109.7
C4B—C3B—H3B118.8H9HA—C9H—H9HB108.2
C2B—C3B—H3B118.8O5H—C10H—C9H109.7 (3)
C3B—C4B—C5B119.7 (3)O5H—C10H—H10C109.7
C3B—C4B—H4B120.1C9H—C10H—H10C109.7
C5B—C4B—H4B120.1O5H—C10H—H10D109.7
N1B—C5B—C4B121.4 (4)C9H—C10H—H10D109.7
N1B—C5B—C6B120.4 (4)H10C—C10H—H10D108.2
C4B—C5B—C6B118.3 (3)O5H—C11H—C12H109.3 (4)
C7B—C6B—C5B121.1 (3)O5H—C11H—H11C109.8
C7B—C6B—H6B119.5C12H—C11H—H11C109.8
C5B—C6B—H6B119.5O5H—C11H—H11D109.8
C6B—C7B—C2B120.7 (3)C12H—C11H—H11D109.8
C6B—C7B—H7B119.7H11C—C11H—H11D108.3
C2B—C7B—H7B119.7O6H—C12H—C11H109.3 (3)
C5B—N1B—H1BA120 (3)O6H—C12H—H12C109.8
C5B—N1B—H1BB117 (3)C11H—C12H—H12C109.8
H1BA—N1B—H1BB120 (5)O6H—C12H—H12D109.8
C1C—O1C—H1C112 (3)C11H—C12H—H12D109.8
O2C—C1C—O1C121.9 (3)H12C—C12H—H12D108.3
O2C—C1C—C2C121.9 (3)C3I—O1I—C2I112.5 (4)
O1C—C1C—C2C116.1 (3)C5I—O2I—C4I114.5 (4)
C7C—C2C—C3C118.0 (3)C7I—O3I—C6I113.6 (4)
C7C—C2C—C1C121.8 (3)C9I—O4I—C8I111.3 (4)
C3C—C2C—C1C120.1 (3)C11I—O5I—C10I111.4 (4)
C4C—C3C—C2C121.1 (3)C1I—O6I—C12I113.8 (4)
C4C—C3C—H3C119.5O6I—C1I—C2I109.0 (4)
C2C—C3C—H3C119.5O6I—C1I—H1IA109.9
C3C—C4C—C5C121.2 (3)C2I—C1I—H1IA109.9
C3C—C4C—H4C119.4O6I—C1I—H1IB109.9
C5C—C4C—H4C119.4C2I—C1I—H1IB109.9
N1C—C5C—C6C121.5 (4)H1IA—C1I—H1IB108.3
N1C—C5C—C4C121.2 (4)O1I—C2I—C1I111.2 (4)
C6C—C5C—C4C117.3 (3)O1I—C2I—H2IA109.4
C7C—C6C—C5C121.1 (3)C1I—C2I—H2IA109.4
C7C—C6C—H6C119.4O1I—C2I—H2IB109.4
C5C—C6C—H6C119.4C1I—C2I—H2IB109.4
C6C—C7C—C2C121.2 (3)H2IA—C2I—H2IB108.0
C6C—C7C—H7C119.4O1I—C3I—C4I109.0 (4)
C2C—C7C—H7C119.4O1I—C3I—H3IA109.9
C5C—N1C—H1CA115 (3)C4I—C3I—H3IA109.9
C5C—N1C—H1CB119 (4)O1I—C3I—H3IB109.9
H1CA—N1C—H1CB124 (5)C4I—C3I—H3IB109.9
C1D—O1D—H1D109.5H3IA—C3I—H3IB108.3
O2D—C1D—O1D122.0 (3)O2I—C4I—C3I111.3 (4)
O2D—C1D—C2D121.8 (3)O2I—C4I—H4IA109.4
O1D—C1D—C2D116.3 (3)C3I—C4I—H4IA109.4
C3D—C2D—C7D118.1 (3)O2I—C4I—H4IB109.4
C3D—C2D—C1D122.8 (3)C3I—C4I—H4IB109.4
C7D—C2D—C1D119.1 (3)H4IA—C4I—H4IB108.0
C4D—C3D—C2D121.3 (3)O2I—C5I—C6I109.4 (4)
C4D—C3D—H3D119.3O2I—C5I—H5IA109.8
C2D—C3D—H3D119.3C6I—C5I—H5IA109.8
C3D—C4D—C5D120.6 (3)O2I—C5I—H5IB109.8
C3D—C4D—H4D119.7C6I—C5I—H5IB109.8
C5D—C4D—H4D119.7H5IA—C5I—H5IB108.2
N1D—C5D—C6D120.4 (4)O3I—C6I—C5I109.1 (4)
N1D—C5D—C4D122.0 (3)O3I—C6I—H6IA109.9
C6D—C5D—C4D117.7 (3)C5I—C6I—H6IA109.9
C7D—C6D—C5D121.5 (3)O3I—C6I—H6IB109.9
C7D—C6D—H6D119.3C5I—C6I—H6IB109.9
C5D—C6D—H6D119.3H6IA—C6I—H6IB108.3
C6D—C7D—C2D120.8 (3)O3I—C7I—C8I109.2 (4)
C6D—C7D—H7D119.6O3I—C7I—H7IA109.8
C2D—C7D—H7D119.6C8I—C7I—H7IA109.8
C5D—N1D—H1DA122 (4)O3I—C7I—H7IB109.8
C5D—N1D—H1DB119 (3)C8I—C7I—H7IB109.8
H1DA—N1D—H1DB116 (5)H7IA—C7I—H7IB108.3
C1E—O1E—H1E114 (3)O4I—C8I—C7I109.5 (4)
O2E—C1E—O1E122.1 (3)O4I—C8I—H8IA109.8
O2E—C1E—C2E120.4 (3)C7I—C8I—H8IA109.8
O1E—C1E—C2E117.6 (3)O4I—C8I—H8IB109.8
C3E—C2E—C7E118.1 (3)C7I—C8I—H8IB109.8
C3E—C2E—C1E121.9 (3)H8IA—C8I—H8IB108.2
C7E—C2E—C1E120.0 (3)O4I—C9I—C10I111.3 (5)
C4E—C3E—C2E121.3 (3)O4I—C9I—H9IA109.4
C4E—C3E—H3E119.3C10I—C9I—H9IA109.4
C2E—C3E—H3E119.3O4I—C9I—H9IB109.4
C3E—C4E—C5E120.6 (3)C10I—C9I—H9IB109.4
C3E—C4E—H4E119.7H9IA—C9I—H9IB108.0
C5E—C4E—H4E119.7O5I—C10I—C9I107.7 (4)
N1E—C5E—C6E121.4 (3)O5I—C10I—H10E110.2
N1E—C5E—C4E120.7 (3)C9I—C10I—H10E110.2
C6E—C5E—C4E117.9 (3)O5I—C10I—H10F110.2
C7E—C6E—C5E120.8 (3)C9I—C10I—H10F110.2
C7E—C6E—H6E119.6H10E—C10I—H10F108.5
C5E—C6E—H6E119.6O5I—C11I—C12I108.3 (4)
C6E—C7E—C2E121.2 (3)O5I—C11I—H11E110.0
C6E—C7E—H7E119.4C12I—C11I—H11E110.0
C2E—C7E—H7E119.4O5I—C11I—H11F110.0
C5E—N1E—H1EA124 (2)C12I—C11I—H11F110.0
C5E—N1E—H1EB111 (3)H11E—C11I—H11F108.4
H1EA—N1E—H1EB125 (4)O6I—C12I—C11I110.0 (4)
C1F—O1F—H1F113 (3)O6I—C12I—H12E109.7
C1F—O2F—H1G120 (3)C11I—C12I—H12E109.7
O2F—C1F—O1F122.4 (3)O6I—C12I—H12F109.7
O2F—C1F—C2F119.0 (3)C11I—C12I—H12F109.7
O1F—C1F—C2F118.6 (3)H12E—C12I—H12F108.2
C3F—C2F—C7F118.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12A—H12A···O2Bi0.992.653.550 (5)151
O1B—H1B···O2Bii1.04 (6)1.57 (6)2.604 (4)175 (5)
N1B—H1BA···O6I0.85 (5)2.37 (5)3.138 (5)150 (4)
N1B—H1BB···O2I0.86 (6)2.60 (5)3.280 (5)138 (4)
N1B—H1BB···O3I0.86 (6)2.27 (6)3.061 (5)154 (5)
O1C—H1C···O2D1.01 (5)1.60 (6)2.600 (3)170 (5)
N1C—H1CA···O4Aiii0.83 (5)2.58 (5)3.153 (5)127 (4)
N1C—H1CA···O5Aiii0.83 (5)2.25 (5)3.055 (5)164 (4)
N1C—H1CB···O1Aiii0.81 (5)2.25 (5)2.998 (5)153 (5)
O1D—H1D···O2C0.841.782.617 (3)172
N1D—H1DA···O4Hiv0.85 (5)2.23 (5)2.961 (4)144 (5)
N1D—H1DB···O5Hiv0.86 (5)2.64 (5)3.102 (4)114 (4)
N1D—H1DB···O6Hiv0.86 (5)2.30 (5)3.148 (5)165 (4)
O1E—H1E···O2Ev1.12 (6)1.50 (7)2.622 (3)172 (5)
N1E—H1EA···O1H0.89 (4)2.30 (4)3.069 (4)144 (3)
N1E—H1EA···O2H0.89 (4)2.63 (4)3.403 (5)147 (3)
N1E—H1EB···O5H0.82 (4)2.33 (5)3.125 (5)162 (4)
O1F—H1F···O1G1.17 (7)2.64 (7)3.483 (4)128 (4)
O1F—H1F···O2G1.17 (7)1.44 (7)2.600 (3)171 (6)
O2G—H1F···O2F1.44 (7)2.42 (7)3.370 (4)119 (4)
N1F—H1FA···O3I0.87 (4)2.33 (4)3.083 (5)145 (4)
N1F—H1FA···O4I0.87 (4)2.63 (4)3.380 (5)145 (3)
N1F—H1FB···O1I0.80 (6)2.41 (6)3.165 (5)159 (5)
N1F—H1FB···O6I0.80 (6)2.65 (6)3.215 (5)129 (5)
O2F—H1G···O2G1.35 (7)2.50 (7)3.370 (4)119 (4)
O1G—H1G···O1F1.25 (7)2.62 (7)3.483 (4)124 (4)
O1G—H1G···O2F1.25 (7)1.35 (7)2.604 (3)177 (6)
N1G—H1GA···O6Avi0.84 (4)2.24 (4)3.058 (5)168 (3)
N1G—H1GB···O3Avi0.82 (5)2.59 (5)3.353 (5)156 (4)
N1G—H1GB···O4Avi0.82 (5)2.41 (5)3.058 (4)136 (4)
C3H—H3HB···O2Cvii0.992.633.504 (5)148
C7I—H7IA···O2D0.992.533.494 (6)164
Symmetry codes: (i) x+1, y, z; (ii) x, y, z; (iii) x+1, y+1, z; (iv) x+1/2, y1/2, z+1/2; (v) x, y+1, z; (vi) x+1/2, y+1/2, z+1/2; (vii) x1, y, z.
(2) 18-crown-6/4-aminobenzoic acid/bis(3,5-dinitrobenzoic acid) top
Crystal data top
C12H24O6·C7H3N2O6·C7H4N2O6·C7H8NO2Z = 2
Mr = 825.69F(000) = 864
Triclinic, P1Dx = 1.435 Mg m3
a = 7.6055 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.0157 (4) ÅCell parameters from 9094 reflections
c = 16.4476 (4) Åθ = 2.6–24.5°
α = 73.156 (2)°µ = 0.12 mm1
β = 85.540 (2)°T = 173 K
γ = 89.562 (1)°Block, colourless
V = 1911.45 (9) Å30.24 × 0.21 × 0.17 mm
Data collection top
Bruker APEX-II CCD
diffractometer
6336 reflections with I > 2σ(I)
φ and ω scansRint = 0.047
Absorption correction: multi-scan
SADABS (Bruker, 2008)
θmax = 30.0°, θmin = 2.1°
Tmin = 0.971, Tmax = 0.980h = 109
50498 measured reflectionsk = 2222
10356 independent reflectionsl = 2323
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0438P)2 + 0.335P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
10356 reflectionsΔρmax = 0.29 e Å3
543 parametersΔρmin = 0.27 e Å3
Crystal data top
C12H24O6·C7H3N2O6·C7H4N2O6·C7H8NO2γ = 89.562 (1)°
Mr = 825.69V = 1911.45 (9) Å3
Triclinic, P1Z = 2
a = 7.6055 (2) ÅMo Kα radiation
b = 16.0157 (4) ŵ = 0.12 mm1
c = 16.4476 (4) ÅT = 173 K
α = 73.156 (2)°0.24 × 0.21 × 0.17 mm
β = 85.540 (2)°
Data collection top
Bruker APEX-II CCD
diffractometer
10356 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2008)
6336 reflections with I > 2σ(I)
Tmin = 0.971, Tmax = 0.980Rint = 0.047
50498 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.29 e Å3
10356 reflectionsΔρmin = 0.27 e Å3
543 parameters
Special details top

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. H atoms of carboxyl and ammonium groups refined freely

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.70311 (14)0.39418 (6)0.26256 (7)0.0279 (3)
O20.40686 (14)0.40691 (7)0.37024 (7)0.0299 (3)
O30.33487 (14)0.57182 (7)0.39547 (7)0.0299 (3)
O40.62524 (14)0.68320 (7)0.37789 (7)0.0318 (3)
O50.88839 (13)0.67812 (7)0.25440 (7)0.0295 (3)
O60.96446 (14)0.52168 (7)0.21671 (7)0.0305 (3)
C10.6015 (2)0.31942 (10)0.31118 (10)0.0309 (4)
H1A0.64770.29550.36780.037*
H1B0.60850.27360.28160.037*
C20.4151 (2)0.34646 (10)0.32111 (11)0.0327 (4)
H2A0.37180.37410.26440.039*
H2B0.33950.29470.35020.039*
C30.2330 (2)0.43650 (12)0.38119 (14)0.0445 (5)
H3A0.15240.38610.40760.053*
H3B0.19160.46840.32510.053*
C40.2322 (2)0.49527 (12)0.43688 (13)0.0459 (5)
H4A0.10950.51160.44960.055*
H4B0.28120.46440.49140.055*
C50.3488 (2)0.62711 (12)0.44900 (11)0.0374 (4)
H5A0.40830.59590.50040.045*
H5B0.22960.64320.46760.045*
C60.4522 (2)0.70760 (12)0.40082 (12)0.0372 (4)
H6A0.39380.73840.34890.045*
H6B0.45840.74750.43660.045*
C70.7363 (2)0.75782 (11)0.33862 (12)0.0342 (4)
H7A0.75040.79180.37940.041*
H7B0.68230.79590.28840.041*
C80.9121 (2)0.72813 (11)0.31175 (11)0.0328 (4)
H8A0.98970.77930.28340.039*
H8B0.96840.69220.36230.039*
C91.0512 (2)0.66551 (11)0.21064 (12)0.0354 (4)
H9A1.13930.64140.25220.042*
H9B1.09720.72210.17230.042*
C101.0214 (2)0.60366 (11)0.15975 (12)0.0356 (4)
H10A0.93070.62690.11930.043*
H10B1.13210.59670.12660.043*
C110.9625 (2)0.45348 (11)0.17689 (11)0.0334 (4)
H11A1.08440.44090.15850.040*
H11B0.89410.47150.12600.040*
C120.8797 (2)0.37377 (10)0.23964 (11)0.0315 (4)
H12A0.87950.32500.21390.038*
H12B0.94730.35600.29080.038*
O1A0.3640 (2)0.68524 (10)0.11356 (8)0.0602 (4)
O2A0.28934 (18)0.80021 (8)0.06845 (8)0.0394 (3)
H20.247 (3)0.8174 (15)0.1184 (15)0.067 (7)*
N1A0.60982 (18)0.56401 (9)0.26723 (8)0.0204 (3)
H1AA0.642 (2)0.5062 (13)0.2708 (11)0.041 (5)*
H1AB0.524 (3)0.5626 (13)0.3143 (14)0.065 (7)*
H1AC0.706 (3)0.5971 (13)0.2738 (13)0.057 (6)*
C1A0.42739 (19)0.68403 (10)0.02546 (9)0.0232 (3)
C2A0.4710 (2)0.59662 (10)0.04806 (10)0.0294 (4)
H2AA0.46120.56420.00850.035*
C3A0.5286 (2)0.55583 (10)0.12741 (10)0.0264 (3)
H3AA0.55590.49560.14310.032*
C4A0.54573 (18)0.60465 (9)0.18336 (9)0.0189 (3)
C5A0.50679 (19)0.69238 (9)0.16142 (9)0.0229 (3)
H5AA0.52180.72530.20010.027*
C6A0.4456 (2)0.73183 (10)0.08238 (10)0.0239 (3)
H6AA0.41600.79180.06720.029*
C7A0.3578 (2)0.72278 (11)0.05982 (10)0.0292 (4)
O1B0.0111 (2)0.76497 (10)0.54022 (10)0.0747 (5)
O2B0.09603 (19)0.83518 (9)0.41577 (9)0.0542 (4)
O3B0.3662 (2)1.11868 (8)0.36788 (7)0.0485 (4)
O4B0.44509 (17)1.15604 (7)0.47528 (8)0.0428 (3)
O5B0.1948 (2)0.99992 (9)0.76123 (8)0.0619 (4)
O6B0.15325 (16)0.85646 (8)0.78650 (7)0.0366 (3)
N1B0.06927 (18)0.82635 (9)0.49122 (10)0.0335 (3)
N2B0.37000 (18)1.10703 (8)0.44430 (8)0.0281 (3)
C1B0.1869 (2)0.94501 (10)0.64432 (9)0.0242 (3)
C2B0.12106 (19)0.88119 (10)0.61256 (10)0.0242 (3)
H2BA0.06610.82970.64990.029*
C3B0.13715 (19)0.89413 (9)0.52551 (10)0.0234 (3)
C4B0.21711 (19)0.96697 (9)0.46849 (9)0.0228 (3)
H4BA0.22750.97430.40890.027*
C5B0.28120 (19)1.02872 (9)0.50258 (9)0.0218 (3)
C6B0.2675 (2)1.01959 (9)0.58902 (9)0.0241 (3)
H6BA0.31261.06370.61020.029*
C7B0.1768 (2)0.93243 (11)0.73967 (10)0.0305 (4)
O1C0.8772 (2)0.69194 (8)0.92314 (9)0.0544 (4)
O2C0.79118 (18)0.74970 (9)0.79701 (9)0.0510 (4)
O3C0.6006 (2)1.04864 (9)0.71583 (8)0.0550 (4)
O4C0.5860 (2)1.12038 (9)0.80821 (9)0.0622 (4)
O5C0.77940 (19)0.99684 (8)1.08784 (8)0.0456 (3)
H50.795 (3)0.9971 (16)1.1466 (17)0.088 (8)*
O6C0.9104 (2)0.86733 (9)1.12233 (9)0.0610 (4)
N1C0.82041 (19)0.75270 (9)0.86820 (10)0.0368 (4)
N2C0.6199 (2)1.05504 (10)0.78673 (9)0.0396 (4)
C1C0.7920 (2)0.91833 (10)0.98777 (10)0.0277 (4)
C2C0.8254 (2)0.84092 (10)0.96773 (10)0.0289 (4)
H2CA0.87430.79281.00750.035*
C3C0.7864 (2)0.83507 (10)0.88930 (10)0.0281 (4)
C4C0.7175 (2)0.90338 (11)0.82864 (10)0.0294 (4)
H4CA0.69160.89820.77470.035*
C5C0.6881 (2)0.97944 (10)0.85049 (10)0.0285 (4)
C6C0.7223 (2)0.98824 (10)0.92880 (10)0.0291 (4)
H6CA0.69841.04140.94200.035*
C7C0.8335 (2)0.92424 (11)1.07375 (11)0.0350 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0332 (6)0.0175 (5)0.0324 (6)0.0020 (5)0.0013 (5)0.0067 (5)
O20.0262 (6)0.0291 (6)0.0355 (6)0.0001 (5)0.0036 (5)0.0107 (5)
O30.0301 (6)0.0298 (6)0.0295 (6)0.0026 (5)0.0036 (5)0.0096 (5)
O40.0306 (6)0.0296 (6)0.0403 (7)0.0022 (5)0.0023 (5)0.0183 (5)
O50.0220 (6)0.0276 (6)0.0425 (7)0.0031 (4)0.0008 (5)0.0162 (5)
O60.0345 (6)0.0215 (6)0.0358 (6)0.0004 (5)0.0025 (5)0.0103 (5)
C10.0461 (10)0.0182 (8)0.0277 (9)0.0023 (7)0.0052 (7)0.0049 (7)
C20.0407 (10)0.0222 (8)0.0342 (9)0.0081 (7)0.0089 (8)0.0051 (7)
C30.0242 (9)0.0292 (9)0.0752 (14)0.0054 (7)0.0018 (9)0.0090 (10)
C40.0349 (10)0.0362 (10)0.0565 (13)0.0002 (8)0.0205 (9)0.0040 (9)
C50.0339 (10)0.0527 (11)0.0317 (9)0.0054 (8)0.0008 (8)0.0228 (9)
C60.0341 (10)0.0415 (10)0.0465 (11)0.0053 (8)0.0047 (8)0.0292 (9)
C70.0384 (10)0.0272 (9)0.0434 (10)0.0006 (7)0.0101 (8)0.0184 (8)
C80.0332 (9)0.0271 (8)0.0422 (10)0.0059 (7)0.0103 (8)0.0143 (8)
C90.0213 (8)0.0265 (9)0.0549 (12)0.0020 (7)0.0033 (8)0.0078 (8)
C100.0299 (9)0.0305 (9)0.0428 (10)0.0007 (7)0.0102 (8)0.0082 (8)
C110.0322 (9)0.0319 (9)0.0403 (10)0.0061 (7)0.0021 (8)0.0183 (8)
C120.0343 (9)0.0233 (8)0.0402 (10)0.0070 (7)0.0064 (8)0.0139 (7)
O1A0.0966 (12)0.0637 (10)0.0307 (7)0.0390 (9)0.0283 (7)0.0249 (7)
O2A0.0598 (8)0.0307 (7)0.0275 (7)0.0119 (6)0.0175 (6)0.0048 (5)
N1A0.0225 (7)0.0199 (7)0.0194 (6)0.0011 (5)0.0039 (5)0.0060 (5)
C1A0.0223 (8)0.0267 (8)0.0199 (7)0.0022 (6)0.0003 (6)0.0060 (6)
C2A0.0389 (10)0.0285 (9)0.0259 (8)0.0095 (7)0.0076 (7)0.0151 (7)
C3A0.0339 (9)0.0202 (8)0.0271 (8)0.0063 (7)0.0057 (7)0.0094 (7)
C4A0.0156 (7)0.0217 (7)0.0190 (7)0.0008 (6)0.0008 (6)0.0054 (6)
C5A0.0271 (8)0.0196 (7)0.0244 (8)0.0009 (6)0.0038 (6)0.0097 (6)
C6A0.0270 (8)0.0179 (7)0.0260 (8)0.0011 (6)0.0035 (6)0.0048 (6)
C7A0.0310 (9)0.0331 (9)0.0229 (8)0.0044 (7)0.0032 (7)0.0070 (7)
O1B0.1197 (14)0.0518 (9)0.0528 (9)0.0536 (9)0.0034 (9)0.0169 (8)
O2B0.0728 (10)0.0584 (9)0.0429 (8)0.0199 (7)0.0012 (7)0.0330 (7)
O3B0.0875 (10)0.0349 (7)0.0206 (6)0.0136 (7)0.0004 (6)0.0046 (5)
O4B0.0634 (9)0.0291 (6)0.0348 (7)0.0174 (6)0.0102 (6)0.0058 (6)
O5B0.1249 (14)0.0416 (8)0.0220 (7)0.0104 (8)0.0024 (8)0.0141 (6)
O6B0.0465 (7)0.0349 (7)0.0231 (6)0.0009 (5)0.0073 (5)0.0012 (5)
N1B0.0363 (8)0.0290 (8)0.0404 (9)0.0029 (6)0.0073 (7)0.0168 (7)
N2B0.0383 (8)0.0206 (7)0.0250 (7)0.0018 (6)0.0047 (6)0.0055 (6)
C1B0.0286 (8)0.0236 (8)0.0206 (8)0.0049 (6)0.0048 (6)0.0063 (6)
C2B0.0241 (8)0.0207 (7)0.0270 (8)0.0017 (6)0.0021 (6)0.0058 (6)
C3B0.0252 (8)0.0210 (7)0.0276 (8)0.0024 (6)0.0061 (6)0.0117 (6)
C4B0.0272 (8)0.0237 (8)0.0202 (7)0.0066 (6)0.0065 (6)0.0095 (6)
C5B0.0278 (8)0.0169 (7)0.0204 (7)0.0028 (6)0.0039 (6)0.0043 (6)
C6B0.0310 (8)0.0200 (7)0.0237 (8)0.0038 (6)0.0072 (7)0.0090 (6)
C7B0.0370 (9)0.0320 (9)0.0230 (8)0.0004 (7)0.0044 (7)0.0081 (7)
O1C0.0822 (11)0.0285 (7)0.0540 (9)0.0153 (7)0.0014 (8)0.0156 (7)
O2C0.0572 (9)0.0512 (8)0.0625 (9)0.0123 (7)0.0181 (7)0.0417 (8)
O3C0.0865 (11)0.0552 (9)0.0285 (7)0.0216 (8)0.0179 (7)0.0178 (7)
O4C0.1129 (13)0.0356 (8)0.0468 (8)0.0325 (8)0.0301 (8)0.0203 (7)
O5C0.0786 (10)0.0354 (7)0.0283 (7)0.0097 (7)0.0097 (7)0.0168 (6)
O6C0.1080 (13)0.0447 (8)0.0338 (7)0.0255 (8)0.0263 (8)0.0123 (7)
N1C0.0383 (9)0.0304 (8)0.0475 (10)0.0030 (7)0.0016 (7)0.0218 (7)
N2C0.0564 (10)0.0347 (8)0.0300 (8)0.0117 (7)0.0090 (7)0.0121 (7)
C1C0.0344 (9)0.0259 (8)0.0235 (8)0.0002 (7)0.0006 (7)0.0090 (7)
C2C0.0333 (9)0.0247 (8)0.0279 (9)0.0025 (7)0.0011 (7)0.0074 (7)
C3C0.0287 (9)0.0256 (8)0.0339 (9)0.0009 (7)0.0035 (7)0.0164 (7)
C4C0.0303 (9)0.0347 (9)0.0272 (8)0.0014 (7)0.0012 (7)0.0156 (7)
C5C0.0346 (9)0.0258 (8)0.0260 (8)0.0058 (7)0.0030 (7)0.0089 (7)
C6C0.0413 (10)0.0224 (8)0.0259 (8)0.0018 (7)0.0005 (7)0.0114 (7)
C7C0.0514 (11)0.0272 (9)0.0257 (9)0.0002 (8)0.0017 (8)0.0069 (7)
Geometric parameters (Å, º) top
O1—C11.4260 (18)C1A—C6A1.385 (2)
O1—C121.4280 (19)C1A—C2A1.385 (2)
O2—C31.417 (2)C1A—C7A1.496 (2)
O2—C21.4279 (19)C2A—C3A1.383 (2)
O3—C41.423 (2)C2A—H2AA0.9500
O3—C51.4276 (19)C3A—C4A1.383 (2)
O4—C61.424 (2)C3A—H3AA0.9500
O4—C71.4291 (19)C4A—C5A1.381 (2)
O5—C81.4249 (18)C5A—C6A1.386 (2)
O5—C91.4261 (19)C5A—H5AA0.9500
O6—C101.4220 (19)C6A—H6AA0.9500
O6—C111.4277 (18)O1B—N1B1.2096 (19)
C1—C21.490 (2)O2B—N1B1.2087 (18)
C1—H1A0.9900O3B—N2B1.2187 (17)
C1—H1B0.9900O4B—N2B1.2188 (16)
C2—H2A0.9900O5B—C7B1.243 (2)
C2—H2B0.9900O6B—C7B1.2428 (19)
C3—C41.491 (3)N1B—C3B1.4738 (19)
C3—H3A0.9900N2B—C5B1.4710 (19)
C3—H3B0.9900C1B—C6B1.387 (2)
C4—H4A0.9900C1B—C2B1.388 (2)
C4—H4B0.9900C1B—C7B1.518 (2)
C5—C61.495 (2)C2B—C3B1.382 (2)
C5—H5A0.9900C2B—H2BA0.9500
C5—H5B0.9900C3B—C4B1.378 (2)
C6—H6A0.9900C4B—C5B1.379 (2)
C6—H6B0.9900C4B—H4BA0.9500
C7—C81.493 (2)C5B—C6B1.382 (2)
C7—H7A0.9900C6B—H6BA0.9500
C7—H7B0.9900O1C—N1C1.2226 (19)
C8—H8A0.9900O2C—N1C1.2231 (19)
C8—H8B0.9900O3C—N2C1.2199 (18)
C9—C101.499 (2)O4C—N2C1.2176 (18)
C9—H9A0.9900O5C—C7C1.307 (2)
C9—H9B0.9900O5C—H50.98 (3)
C10—H10A0.9900O6C—C7C1.206 (2)
C10—H10B0.9900N1C—C3C1.475 (2)
C11—C121.496 (2)N2C—C5C1.474 (2)
C11—H11A0.9900C1C—C6C1.384 (2)
C11—H11B0.9900C1C—C2C1.389 (2)
C12—H12A0.9900C1C—C7C1.502 (2)
C12—H12B0.9900C2C—C3C1.375 (2)
O1A—C7A1.2023 (19)C2C—H2CA0.9500
O2A—C7A1.315 (2)C3C—C4C1.381 (2)
O2A—H20.87 (2)C4C—C5C1.378 (2)
N1A—C4A1.4641 (18)C4C—H4CA0.9500
N1A—H1AA0.942 (19)C5C—C6C1.380 (2)
N1A—H1AB0.97 (2)C6C—H6CA0.9500
N1A—H1AC0.94 (2)
C1—O1—C12113.04 (11)H1AA—N1A—H1AB108.1 (16)
C3—O2—C2111.90 (13)C4A—N1A—H1AC108.4 (12)
C4—O3—C5111.99 (13)H1AA—N1A—H1AC111.5 (17)
C6—O4—C7111.62 (12)H1AB—N1A—H1AC106.1 (17)
C8—O5—C9111.72 (12)C6A—C1A—C2A119.55 (14)
C10—O6—C11113.34 (13)C6A—C1A—C7A122.39 (14)
O1—C1—C2108.20 (12)C2A—C1A—C7A118.04 (14)
O1—C1—H1A110.1C3A—C2A—C1A120.95 (14)
C2—C1—H1A110.1C3A—C2A—H2AA119.5
O1—C1—H1B110.1C1A—C2A—H2AA119.5
C2—C1—H1B110.1C4A—C3A—C2A118.59 (14)
H1A—C1—H1B108.4C4A—C3A—H3AA120.7
O2—C2—C1108.83 (13)C2A—C3A—H3AA120.7
O2—C2—H2A109.9C5A—C4A—C3A121.41 (13)
C1—C2—H2A109.9C5A—C4A—N1A118.52 (13)
O2—C2—H2B109.9C3A—C4A—N1A120.05 (13)
C1—C2—H2B109.9C4A—C5A—C6A119.27 (14)
H2A—C2—H2B108.3C4A—C5A—H5AA120.4
O2—C3—C4109.08 (15)C6A—C5A—H5AA120.4
O2—C3—H3A109.9C1A—C6A—C5A120.18 (14)
C4—C3—H3A109.9C1A—C6A—H6AA119.9
O2—C3—H3B109.9C5A—C6A—H6AA119.9
C4—C3—H3B109.9O1A—C7A—O2A124.69 (15)
H3A—C3—H3B108.3O1A—C7A—C1A122.28 (15)
O3—C4—C3110.02 (15)O2A—C7A—C1A113.03 (14)
O3—C4—H4A109.7O2B—N1B—O1B123.53 (15)
C3—C4—H4A109.7O2B—N1B—C3B118.40 (14)
O3—C4—H4B109.7O1B—N1B—C3B118.07 (14)
C3—C4—H4B109.7O3B—N2B—O4B123.75 (14)
H4A—C4—H4B108.2O3B—N2B—C5B118.22 (13)
O3—C5—C6109.32 (13)O4B—N2B—C5B118.03 (13)
O3—C5—H5A109.8C6B—C1B—C2B120.01 (14)
C6—C5—H5A109.8C6B—C1B—C7B119.58 (14)
O3—C5—H5B109.8C2B—C1B—C7B120.38 (14)
C6—C5—H5B109.8C3B—C2B—C1B118.55 (14)
H5A—C5—H5B108.3C3B—C2B—H2BA120.7
O4—C6—C5108.80 (14)C1B—C2B—H2BA120.7
O4—C6—H6A109.9C4B—C3B—C2B123.26 (14)
C5—C6—H6A109.9C4B—C3B—N1B117.76 (13)
O4—C6—H6B109.9C2B—C3B—N1B118.97 (14)
C5—C6—H6B109.9C3B—C4B—C5B116.41 (13)
H6A—C6—H6B108.3C3B—C4B—H4BA121.8
O4—C7—C8109.02 (13)C5B—C4B—H4BA121.8
O4—C7—H7A109.9C4B—C5B—C6B122.84 (14)
C8—C7—H7A109.9C4B—C5B—N2B118.38 (13)
O4—C7—H7B109.9C6B—C5B—N2B118.77 (13)
C8—C7—H7B109.9C5B—C6B—C1B118.93 (14)
H7A—C7—H7B108.3C5B—C6B—H6BA120.5
O5—C8—C7108.95 (13)C1B—C6B—H6BA120.5
O5—C8—H8A109.9O5B—C7B—O6B127.95 (16)
C7—C8—H8A109.9O5B—C7B—C1B115.49 (14)
O5—C8—H8B109.9O6B—C7B—C1B116.55 (14)
C7—C8—H8B109.9C7C—O5C—H5111.7 (14)
H8A—C8—H8B108.3O1C—N1C—O2C124.33 (14)
O5—C9—C10109.13 (13)O1C—N1C—C3C117.58 (15)
O5—C9—H9A109.9O2C—N1C—C3C118.09 (15)
C10—C9—H9A109.9O4C—N2C—O3C123.84 (15)
O5—C9—H9B109.9O4C—N2C—C5C117.78 (14)
C10—C9—H9B109.9O3C—N2C—C5C118.38 (14)
H9A—C9—H9B108.3C6C—C1C—C2C119.94 (15)
O6—C10—C9108.64 (14)C6C—C1C—C7C121.31 (14)
O6—C10—H10A110.0C2C—C1C—C7C118.75 (15)
C9—C10—H10A110.0C3C—C2C—C1C118.91 (15)
O6—C10—H10B110.0C3C—C2C—H2CA120.5
C9—C10—H10B110.0C1C—C2C—H2CA120.5
H10A—C10—H10B108.3C2C—C3C—C4C122.91 (14)
O6—C11—C12108.56 (13)C2C—C3C—N1C118.97 (15)
O6—C11—H11A110.0C4C—C3C—N1C118.12 (15)
C12—C11—H11A110.0C5C—C4C—C3C116.48 (15)
O6—C11—H11B110.0C5C—C4C—H4CA121.8
C12—C11—H11B110.0C3C—C4C—H4CA121.8
H11A—C11—H11B108.4C4C—C5C—C6C122.89 (15)
O1—C12—C11108.01 (12)C4C—C5C—N2C118.40 (14)
O1—C12—H12A110.1C6C—C5C—N2C118.70 (14)
C11—C12—H12A110.1C5C—C6C—C1C118.86 (14)
O1—C12—H12B110.1C5C—C6C—H6CA120.6
C11—C12—H12B110.1C1C—C6C—H6CA120.6
H12A—C12—H12B108.4O6C—C7C—O5C125.45 (16)
C7A—O2A—H2107.8 (15)O6C—C7C—C1C121.97 (15)
C4A—N1A—H1AA108.8 (11)O5C—C7C—C1C112.57 (15)
C4A—N1A—H1AB113.9 (13)
C12—O1—C1—C2172.39 (13)C2B—C3B—C4B—C5B0.5 (2)
C3—O2—C2—C1179.13 (14)N1B—C3B—C4B—C5B179.23 (13)
O1—C1—C2—O264.66 (16)C3B—C4B—C5B—C6B0.0 (2)
C2—O2—C3—C4176.87 (14)C3B—C4B—C5B—N2B179.11 (13)
C5—O3—C4—C3175.63 (15)O3B—N2B—C5B—C4B7.9 (2)
O2—C3—C4—O365.0 (2)O4B—N2B—C5B—C4B171.20 (14)
C4—O3—C5—C6177.92 (14)O3B—N2B—C5B—C6B172.92 (15)
C7—O4—C6—C5174.48 (13)O4B—N2B—C5B—C6B8.0 (2)
O3—C5—C6—O461.86 (18)C4B—C5B—C6B—C1B0.4 (2)
C6—O4—C7—C8176.84 (14)N2B—C5B—C6B—C1B178.74 (13)
C9—O5—C8—C7165.93 (13)C2B—C1B—C6B—C5B0.2 (2)
O4—C7—C8—O558.47 (18)C7B—C1B—C6B—C5B177.77 (14)
C8—O5—C9—C10173.09 (14)C6B—C1B—C7B—O5B20.2 (2)
C11—O6—C10—C9169.38 (13)C2B—C1B—C7B—O5B161.81 (16)
O5—C9—C10—O662.57 (17)C6B—C1B—C7B—O6B159.23 (15)
C10—O6—C11—C12173.00 (13)C2B—C1B—C7B—O6B18.8 (2)
C1—O1—C12—C11170.27 (13)C6C—C1C—C2C—C3C0.7 (2)
O6—C11—C12—O161.15 (17)C7C—C1C—C2C—C3C179.54 (15)
C6A—C1A—C2A—C3A1.5 (2)C1C—C2C—C3C—C4C1.0 (2)
C7A—C1A—C2A—C3A177.11 (15)C1C—C2C—C3C—N1C179.52 (14)
C1A—C2A—C3A—C4A1.4 (2)O1C—N1C—C3C—C2C2.3 (2)
C2A—C3A—C4A—C5A0.1 (2)O2C—N1C—C3C—C2C177.30 (15)
C2A—C3A—C4A—N1A178.75 (14)O1C—N1C—C3C—C4C178.20 (15)
C3A—C4A—C5A—C6A1.5 (2)O2C—N1C—C3C—C4C2.2 (2)
N1A—C4A—C5A—C6A179.85 (13)C2C—C3C—C4C—C5C0.2 (2)
C2A—C1A—C6A—C5A0.1 (2)N1C—C3C—C4C—C5C179.73 (14)
C7A—C1A—C6A—C5A178.46 (14)C3C—C4C—C5C—C6C0.9 (2)
C4A—C5A—C6A—C1A1.4 (2)C3C—C4C—C5C—N2C178.10 (15)
C6A—C1A—C7A—O1A169.77 (17)O4C—N2C—C5C—C4C176.31 (17)
C2A—C1A—C7A—O1A11.7 (2)O3C—N2C—C5C—C4C3.6 (2)
C6A—C1A—C7A—O2A10.8 (2)O4C—N2C—C5C—C6C4.7 (2)
C2A—C1A—C7A—O2A167.74 (14)O3C—N2C—C5C—C6C175.40 (16)
C6B—C1B—C2B—C3B0.3 (2)C4C—C5C—C6C—C1C1.1 (3)
C7B—C1B—C2B—C3B178.26 (14)N2C—C5C—C6C—C1C177.83 (15)
C1B—C2B—C3B—C4B0.7 (2)C2C—C1C—C6C—C5C0.3 (2)
C1B—C2B—C3B—N1B179.37 (13)C7C—C1C—C6C—C5C179.46 (15)
O2B—N1B—C3B—C4B4.4 (2)C6C—C1C—C7C—O6C172.35 (18)
O1B—N1B—C3B—C4B175.29 (16)C2C—C1C—C7C—O6C7.4 (3)
O2B—N1B—C3B—C2B174.40 (15)C6C—C1C—C7C—O5C6.8 (2)
O1B—N1B—C3B—C2B6.0 (2)C2C—C1C—C7C—O5C173.40 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···O10.942 (19)1.89 (2)2.8267 (17)172.6 (16)
N1A—H1AA···O20.942 (19)2.545 (18)2.9607 (17)107.0 (13)
N1A—H1AB···O30.97 (2)1.92 (2)2.8811 (17)171.5 (19)
N1A—H1AC···O40.94 (2)2.53 (2)3.0035 (17)111.4 (14)
N1A—H1AC···O50.94 (2)1.85 (2)2.7639 (17)163.6 (18)
O2A—H2···O6Bi0.87 (2)1.72 (2)2.5883 (16)176 (2)
O5C—H5···O5Bii0.98 (3)1.54 (3)2.5208 (17)175 (2)
Symmetry codes: (i) x, y, z1; (ii) x+1, y+2, z+2.

Experimental details

(1)(2)
Crystal data
Chemical formulaC12H24O6·2(C7H7NO2)C12H24O6·C7H3N2O6·C7H4N2O6·C7H8NO2
Mr538.58825.69
Crystal system, space groupMonoclinic, P21/nTriclinic, P1
Temperature (K)173173
a, b, c (Å)10.3947 (3), 17.5546 (5), 47.2700 (14)7.6055 (2), 16.0157 (4), 16.4476 (4)
α, β, γ (°)90, 91.321 (2), 9073.156 (2), 85.540 (2), 89.562 (1)
V3)8623.3 (4)1911.45 (9)
Z122
Radiation typeMo KαMo Kα
µ (mm1)0.100.12
Crystal size (mm)0.79 × 0.65 × 0.530.24 × 0.21 × 0.17
Data collection
DiffractometerBruker APEX-II CCD
diffractometer
Bruker APEX-II CCD
diffractometer
Absorption correctionMulti-scan
SADABS (Bruker, 2008)
Multi-scan
SADABS (Bruker, 2008)
Tmin, Tmax0.928, 0.9500.971, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
132140, 16030, 10452 50498, 10356, 6336
Rint0.0450.047
(sin θ/λ)max1)0.6200.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.073, 0.199, 1.06 0.047, 0.112, 1.01
No. of reflections1603010356
No. of parameters1114543
No. of restraints60
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(Fo2) + (0.0614P)2 + 16.5586P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0438P)2 + 0.335P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.91, 0.370.29, 0.27

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SAINT, SHELXS97 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2008), CrystalMaker (Palmer, 2005) and Mercury (Macrae et al., 2006), SHELXL2013.

Hydrogen-bond geometry (Å, º) for (1) top
D—H···AD—HH···AD···AD—H···A
C12A—H12A···O2Bi0.992.653.550 (5)151.2
O1B—H1B···O2Bii1.04 (6)1.57 (6)2.604 (4)175 (5)
N1B—H1BA···O6I0.85 (5)2.37 (5)3.138 (5)150 (4)
N1B—H1BB···O2I0.86 (6)2.60 (5)3.280 (5)138 (4)
N1B—H1BB···O3I0.86 (6)2.27 (6)3.061 (5)154 (5)
O1C—H1C···O2D1.01 (5)1.60 (6)2.600 (3)170 (5)
N1C—H1CA···O4Aiii0.83 (5)2.58 (5)3.153 (5)127 (4)
N1C—H1CA···O5Aiii0.83 (5)2.25 (5)3.055 (5)164 (4)
N1C—H1CB···O1Aiii0.81 (5)2.25 (5)2.998 (5)153 (5)
O1D—H1D···O2C0.841.782.617 (3)172.1
N1D—H1DA···O4Hiv0.85 (5)2.23 (5)2.961 (4)144 (5)
N1D—H1DB···O5Hiv0.86 (5)2.64 (5)3.102 (4)114 (4)
N1D—H1DB···O6Hiv0.86 (5)2.30 (5)3.148 (5)165 (4)
O1E—H1E···O2Ev1.12 (6)1.50 (7)2.622 (3)172 (5)
N1E—H1EA···O1H0.89 (4)2.30 (4)3.069 (4)144 (3)
N1E—H1EA···O2H0.89 (4)2.63 (4)3.403 (5)147 (3)
N1E—H1EB···O5H0.82 (4)2.33 (5)3.125 (5)162 (4)
O1F—H1F···O1G1.17 (7)2.64 (7)3.483 (4)128 (4)
O1F—H1F···O2G1.17 (7)1.44 (7)2.600 (3)171 (6)
O2G—H1F···O2F1.44 (7)2.42 (7)3.370 (4)119 (4)
N1F—H1FA···O3I0.87 (4)2.33 (4)3.083 (5)145 (4)
N1F—H1FA···O4I0.87 (4)2.63 (4)3.380 (5)145 (3)
N1F—H1FB···O1I0.80 (6)2.41 (6)3.165 (5)159 (5)
N1F—H1FB···O6I0.80 (6)2.65 (6)3.215 (5)129 (5)
O2F—H1G···O2G1.35 (7)2.50 (7)3.370 (4)119 (4)
O1G—H1G···O1F1.25 (7)2.62 (7)3.483 (4)124 (4)
O1G—H1G···O2F1.25 (7)1.35 (7)2.604 (3)177 (6)
N1G—H1GA···O6Avi0.84 (4)2.24 (4)3.058 (5)168 (3)
N1G—H1GB···O3Avi0.82 (5)2.59 (5)3.353 (5)156 (4)
N1G—H1GB···O4Avi0.82 (5)2.41 (5)3.058 (4)136 (4)
C3H—H3HB···O2Cvii0.992.633.504 (5)147.7
C7I—H7IA···O2D0.992.533.494 (6)164.0
Symmetry codes: (i) x+1, y, z; (ii) x, y, z; (iii) x+1, y+1, z; (iv) x+1/2, y1/2, z+1/2; (v) x, y+1, z; (vi) x+1/2, y+1/2, z+1/2; (vii) x1, y, z.
Hydrogen-bond geometry (Å, º) for (2) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···O10.942 (19)1.89 (2)2.8267 (17)172.6 (16)
N1A—H1AA···O20.942 (19)2.545 (18)2.9607 (17)107.0 (13)
N1A—H1AB···O30.97 (2)1.92 (2)2.8811 (17)171.5 (19)
N1A—H1AC···O40.94 (2)2.53 (2)3.0035 (17)111.4 (14)
N1A—H1AC···O50.94 (2)1.85 (2)2.7639 (17)163.6 (18)
O2A—H2···O6Bi0.87 (2)1.72 (2)2.5883 (16)176 (2)
O5C—H5···O5Bii0.98 (3)1.54 (3)2.5208 (17)175 (2)
Symmetry codes: (i) x, y, z1; (ii) x+1, y+2, z+2.
 

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds