The structure of the title compound, C20H20N4O14·H2O·CH3CN, dimerizes in the solid state to form an open-ended box which holds two H2O and two CH3CN molecules.
Supporting information
CCDC reference: 287429
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.050
- wR factor = 0.119
- Data-to-parameter ratio = 16.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact O2 .. C15 .. 2.91 Ang.
PLAT731_ALERT_1_B Bond Calc 0.84(7), Rep 0.839(10) ...... 7.00 su-Rat
O1W -H1W 1.555 1.555
PLAT735_ALERT_1_B D-H Calc 0.84(7), Rep 0.839(10) ...... 7.00 su-Rat
O1W -H1W 1.555 1.555
PLAT736_ALERT_1_B H...A Calc 2.31(7), Rep 2.314(17) ...... 4.12 su-Rat
H1W -O13 1.555 2.566
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT430_ALERT_2_C Short Inter D...A Contact O9 .. O12 .. 2.88 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O9 .. C16 .. 2.98 Ang.
PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.841(10) ...... 4.00 su-Rat
O1W -H2W 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.841(10) ...... 4.00 su-Rat
O1W -H2W 1.555 1.555
PLAT736_ALERT_1_C H...A Calc 2.10(4), Rep 2.105(16) ...... 2.50 su-Rat
H2W -N5 1.555 1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C20 H20 N4 O14
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C2 H3 N
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3
H2 O
0 ALERT level A = In general: serious problem
4 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
The title compound was synthesized by a literature procedure (Duggan et al., 2001). Yellow crystals suitable for X-ray analysis were grown by slow evaporation of a CH3CN and H2O (1:1 (v/v) solution of the compound.
All H atoms were placed in idealized positions except for the water H atoms. DFIX restraints were placed on O1W—H1W and O1W—H2W fixing their distances to 0.83 Å.
Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL-SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL-DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997).
2,3,11,12-[4',4'',5',5''-Tetranitro]dibenzo- 1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-diene
top
Crystal data top
C20H20N4O14·C2H3N·H2O | F(000) = 624 |
Mr = 599.47 | Dx = 1.509 Mg m−3 |
Triclinic, P1 | Melting point: 500.0 K |
a = 10.766 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.648 (2) Å | Cell parameters from 25863 reflections |
c = 11.813 (2) Å | θ = 4–25° |
α = 69.89 (3)° | µ = 0.13 mm−1 |
β = 74.07 (3)° | T = 173 K |
γ = 75.84 (3)° | Square Prism, yellow |
V = 1319.0 (5) Å3 | 0.2 × 0.17 × 0.13 mm |
Z = 2 | |
Data collection top
Nonius Kappa CCD diffractometer | Rint = 0.089 |
non–profiled ω/phi/2θ scans | θmax = 27.9°, θmin = 3.6° |
25863 measured reflections | h = −12→14 |
6200 independent reflections | k = −15→15 |
3503 reflections with I > 2σ(I) | l = −15→15 |
Refinement top
Refinement on F2 | 2 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.050 | w = 1/[σ2(Fo2) + (0.0527P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.119 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.33 e Å−3 |
6200 reflections | Δρmin = −0.32 e Å−3 |
388 parameters | |
Crystal data top
C20H20N4O14·C2H3N·H2O | γ = 75.84 (3)° |
Mr = 599.47 | V = 1319.0 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.766 (2) Å | Mo Kα radiation |
b = 11.648 (2) Å | µ = 0.13 mm−1 |
c = 11.813 (2) Å | T = 173 K |
α = 69.89 (3)° | 0.2 × 0.17 × 0.13 mm |
β = 74.07 (3)° | |
Data collection top
Nonius Kappa CCD diffractometer | 3503 reflections with I > 2σ(I) |
25863 measured reflections | Rint = 0.089 |
6200 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 2 restraints |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.33 e Å−3 |
6200 reflections | Δρmin = −0.32 e Å−3 |
388 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.02049 (14) | −0.04783 (15) | 0.71817 (13) | 0.0286 (4) | |
N1 | 0.08497 (15) | 0.03473 (17) | 0.69138 (16) | 0.0212 (4) | |
C1 | 0.09711 (18) | 0.11985 (19) | 0.56734 (18) | 0.0160 (5) | |
O2 | 0.13729 (14) | 0.05053 (16) | 0.76382 (14) | 0.0341 (4) | |
N2 | 0.33208 (15) | 0.12392 (18) | 0.54922 (16) | 0.0217 (4) | |
C2 | 0.20964 (17) | 0.17069 (19) | 0.50378 (18) | 0.0156 (5) | |
O3 | 0.36188 (14) | 0.01181 (15) | 0.59397 (15) | 0.0321 (4) | |
N3 | −0.67320 (15) | 1.04738 (17) | 0.22889 (16) | 0.0183 (4) | |
C3 | 0.21171 (18) | 0.25927 (19) | 0.39075 (19) | 0.0166 (5) | |
H3 | 0.2891 | 0.2936 | 0.3477 | 0.02* | |
O4 | 0.39854 (13) | 0.20068 (15) | 0.53746 (14) | 0.0305 (4) | |
N4 | −0.43397 (16) | 1.16356 (17) | 0.11986 (17) | 0.0225 (4) | |
C4 | 0.10158 (18) | 0.29863 (19) | 0.33950 (18) | 0.0151 (4) | |
O5 | −0.11593 (11) | 0.28987 (13) | 0.34810 (12) | 0.0179 (3) | |
N5 | −0.1810 (2) | 0.4509 (2) | 0.5664 (2) | 0.0457 (6) | |
C5 | −0.01232 (17) | 0.24593 (19) | 0.40408 (18) | 0.0150 (4) | |
O6 | −0.37364 (12) | 0.41809 (13) | 0.31948 (14) | 0.0238 (4) | |
C6 | −0.01333 (18) | 0.15724 (19) | 0.51712 (18) | 0.0158 (5) | |
H6 | −0.0899 | 0.1218 | 0.5605 | 0.019* | |
O7 | −0.40666 (12) | 0.66497 (13) | 0.16790 (13) | 0.0226 (4) | |
C7 | −0.23412 (17) | 0.23930 (19) | 0.41428 (19) | 0.0181 (5) | |
H7A | −0.2694 | 0.2631 | 0.4912 | 0.022* | |
H7B | −0.2153 | 0.1477 | 0.4363 | 0.022* | |
O8 | −0.73205 (14) | 0.99783 (14) | 0.33310 (14) | 0.0305 (4) | |
C8 | −0.33139 (19) | 0.28942 (19) | 0.3333 (2) | 0.0202 (5) | |
H8A | −0.291 | 0.2765 | 0.2516 | 0.024* | |
H8B | −0.4074 | 0.2452 | 0.3702 | 0.024* | |
O9 | −0.71560 (13) | 1.14530 (14) | 0.15939 (14) | 0.0249 (4) | |
C9 | −0.47470 (19) | 0.4686 (2) | 0.2514 (2) | 0.0228 (5) | |
H9A | −0.5503 | 0.4245 | 0.2932 | 0.027* | |
H9B | −0.4425 | 0.4587 | 0.1678 | 0.027* | |
O10 | −0.50879 (13) | 1.20624 (14) | 0.20022 (14) | 0.0282 (4) | |
C10 | −0.51535 (18) | 0.6021 (2) | 0.2429 (2) | 0.0238 (5) | |
H10A | −0.593 | 0.6371 | 0.2049 | 0.029* | |
H10B | −0.5384 | 0.6128 | 0.3262 | 0.029* | |
O11 | −0.35600 (15) | 1.22058 (15) | 0.03517 (16) | 0.0375 (4) | |
C11 | −0.42184 (18) | 0.78621 (19) | 0.15826 (18) | 0.0175 (5) | |
O12 | −0.19711 (11) | 0.76582 (13) | 0.06956 (12) | 0.0183 (3) | |
C12 | −0.53883 (17) | 0.8564 (2) | 0.19896 (18) | 0.0170 (5) | |
H12 | −0.6154 | 0.8195 | 0.2362 | 0.02* | |
O13 | 0.06939 (12) | 0.63579 (13) | 0.07761 (12) | 0.0198 (3) | |
C13 | −0.54420 (17) | 0.97959 (19) | 0.18549 (18) | 0.0158 (5) | |
O14 | 0.09253 (12) | 0.38498 (13) | 0.23002 (12) | 0.0181 (3) | |
C14 | −0.43502 (18) | 1.03608 (19) | 0.12722 (18) | 0.0153 (4) | |
C15 | −0.31705 (18) | 0.96735 (19) | 0.08419 (18) | 0.0165 (5) | |
H15 | −0.2425 | 1.0066 | 0.0427 | 0.02* | |
C16 | −0.30806 (17) | 0.8426 (2) | 0.10151 (18) | 0.0162 (5) | |
C17 | −0.08053 (17) | 0.8215 (2) | 0.00916 (19) | 0.0184 (5) | |
H17A | −0.0555 | 0.8529 | 0.0663 | 0.022* | |
H17B | −0.0973 | 0.8921 | −0.064 | 0.022* | |
C18 | 0.02814 (18) | 0.72468 (19) | −0.02932 (18) | 0.0179 (5) | |
H18A | −0.003 | 0.6827 | −0.0738 | 0.021* | |
H18B | 0.1028 | 0.7644 | −0.0856 | 0.021* | |
C19 | 0.16790 (18) | 0.53838 (19) | 0.04634 (19) | 0.0188 (5) | |
H19A | 0.2462 | 0.5728 | −0.0087 | 0.023* | |
H19B | 0.1348 | 0.4976 | 0.0022 | 0.023* | |
C20 | 0.20376 (18) | 0.44587 (19) | 0.16121 (19) | 0.0189 (5) | |
H20A | 0.2806 | 0.3843 | 0.1402 | 0.023* | |
H20B | 0.2263 | 0.488 | 0.211 | 0.023* | |
C21 | −0.1733 (2) | 0.5116 (2) | 0.4661 (2) | 0.0276 (5) | |
C22 | −0.1643 (2) | 0.5876 (2) | 0.3397 (2) | 0.0290 (6) | |
H22A | −0.2285 | 0.5711 | 0.3048 | 0.043* | |
H22B | −0.076 | 0.5681 | 0.2922 | 0.043* | |
H22C | −0.1824 | 0.6753 | 0.3362 | 0.043* | |
O1W | −0.15280 (18) | 0.2267 (2) | 0.7753 (2) | 0.0473 (5) | |
H1W | −0.131 (6) | 0.254 (6) | 0.823 (5) | 0.23 (3)* | |
H2W | −0.149 (5) | 0.291 (3) | 0.714 (4) | 0.19 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0326 (9) | 0.0262 (10) | 0.0224 (9) | −0.0106 (7) | −0.0046 (7) | 0.0015 (7) |
N1 | 0.0194 (9) | 0.0259 (12) | 0.0165 (10) | −0.0011 (8) | −0.0053 (8) | −0.0047 (9) |
C1 | 0.0203 (11) | 0.0152 (12) | 0.0122 (11) | −0.0019 (8) | −0.0031 (8) | −0.0045 (9) |
O2 | 0.0353 (9) | 0.0503 (12) | 0.0210 (9) | −0.0100 (8) | −0.0131 (7) | −0.0082 (8) |
N2 | 0.0176 (9) | 0.0263 (12) | 0.0195 (10) | −0.0015 (8) | −0.0049 (7) | −0.0056 (9) |
C2 | 0.0150 (10) | 0.0164 (12) | 0.0175 (12) | 0.0004 (8) | −0.0053 (8) | −0.0082 (10) |
O3 | 0.0290 (8) | 0.0231 (10) | 0.0380 (10) | 0.0035 (7) | −0.0150 (7) | −0.0004 (8) |
N3 | 0.0169 (9) | 0.0181 (11) | 0.0224 (11) | −0.0030 (8) | −0.0038 (8) | −0.0094 (9) |
C3 | 0.0152 (10) | 0.0167 (12) | 0.0192 (12) | −0.0049 (8) | −0.0010 (8) | −0.0075 (10) |
O4 | 0.0212 (8) | 0.0370 (11) | 0.0385 (10) | −0.0103 (7) | −0.0116 (7) | −0.0094 (8) |
N4 | 0.0173 (9) | 0.0212 (11) | 0.0285 (11) | −0.0002 (8) | −0.0057 (8) | −0.0083 (9) |
C4 | 0.0173 (10) | 0.0117 (11) | 0.0142 (11) | −0.0008 (8) | −0.0015 (8) | −0.0037 (9) |
O5 | 0.0129 (7) | 0.0199 (9) | 0.0187 (8) | −0.0047 (6) | −0.0044 (6) | −0.0006 (7) |
N5 | 0.0694 (16) | 0.0335 (14) | 0.0317 (14) | −0.0045 (11) | −0.0094 (11) | −0.0103 (12) |
C5 | 0.0142 (10) | 0.0163 (12) | 0.0158 (11) | −0.0010 (8) | −0.0042 (8) | −0.0065 (9) |
O6 | 0.0204 (8) | 0.0153 (9) | 0.0382 (10) | 0.0000 (6) | −0.0138 (7) | −0.0071 (7) |
C6 | 0.0151 (10) | 0.0156 (12) | 0.0169 (11) | −0.0046 (8) | −0.0006 (8) | −0.0057 (10) |
O7 | 0.0142 (7) | 0.0152 (9) | 0.0350 (9) | −0.0027 (6) | −0.0008 (6) | −0.0064 (7) |
C7 | 0.0147 (10) | 0.0168 (12) | 0.0208 (12) | −0.0063 (8) | −0.0015 (8) | −0.0023 (10) |
O8 | 0.0268 (8) | 0.0261 (10) | 0.0303 (10) | −0.0068 (7) | 0.0092 (7) | −0.0083 (8) |
C8 | 0.0160 (10) | 0.0175 (13) | 0.0250 (13) | −0.0031 (8) | −0.0032 (9) | −0.0044 (10) |
O9 | 0.0243 (8) | 0.0231 (10) | 0.0271 (9) | 0.0065 (7) | −0.0126 (7) | −0.0086 (8) |
C9 | 0.0165 (10) | 0.0182 (13) | 0.0344 (14) | −0.0036 (9) | −0.0093 (9) | −0.0050 (11) |
O10 | 0.0253 (8) | 0.0273 (10) | 0.0366 (10) | 0.0013 (7) | −0.0049 (7) | −0.0202 (8) |
C10 | 0.0122 (10) | 0.0193 (13) | 0.0363 (14) | −0.0046 (9) | −0.0030 (9) | −0.0040 (11) |
O11 | 0.0354 (9) | 0.0234 (10) | 0.0465 (11) | −0.0142 (8) | 0.0094 (8) | −0.0091 (8) |
C11 | 0.0195 (10) | 0.0150 (12) | 0.0171 (11) | −0.0036 (9) | −0.0055 (8) | −0.0018 (10) |
O12 | 0.0119 (7) | 0.0160 (8) | 0.0227 (8) | −0.0012 (6) | −0.0010 (6) | −0.0033 (7) |
C12 | 0.0126 (10) | 0.0183 (12) | 0.0178 (12) | −0.0034 (8) | −0.0020 (8) | −0.0027 (9) |
O13 | 0.0178 (7) | 0.0196 (9) | 0.0153 (8) | 0.0032 (6) | −0.0021 (6) | −0.0023 (7) |
C13 | 0.0142 (10) | 0.0190 (13) | 0.0140 (11) | 0.0014 (8) | −0.0056 (8) | −0.0055 (10) |
O14 | 0.0139 (7) | 0.0175 (8) | 0.0183 (8) | −0.0043 (6) | −0.0029 (6) | 0.0012 (7) |
C14 | 0.0173 (10) | 0.0153 (12) | 0.0153 (11) | −0.0017 (8) | −0.0070 (8) | −0.0049 (9) |
C15 | 0.0157 (10) | 0.0174 (12) | 0.0158 (11) | −0.0028 (8) | −0.0057 (8) | −0.0023 (9) |
C16 | 0.0139 (10) | 0.0201 (13) | 0.0140 (11) | 0.0002 (8) | −0.0050 (8) | −0.0049 (9) |
C17 | 0.0107 (10) | 0.0210 (13) | 0.0198 (12) | −0.0042 (8) | −0.0004 (8) | −0.0029 (10) |
C18 | 0.0187 (10) | 0.0172 (12) | 0.0137 (11) | −0.0019 (8) | −0.0042 (8) | 0.0005 (9) |
C19 | 0.0159 (10) | 0.0171 (12) | 0.0181 (12) | −0.0021 (8) | 0.0008 (8) | −0.0025 (10) |
C20 | 0.0125 (10) | 0.0144 (12) | 0.0240 (12) | −0.0035 (8) | 0.0000 (8) | −0.0007 (10) |
C21 | 0.0307 (12) | 0.0228 (14) | 0.0308 (16) | −0.0027 (10) | −0.0036 (10) | −0.0134 (12) |
C22 | 0.0309 (12) | 0.0253 (14) | 0.0271 (14) | −0.0036 (10) | −0.0018 (10) | −0.0073 (11) |
O1W | 0.0468 (11) | 0.0504 (14) | 0.0398 (12) | −0.0001 (9) | −0.0073 (9) | −0.0144 (11) |
Geometric parameters (Å, º) top
O1—N1 | 1.226 (2) | C9—H9A | 0.99 |
N1—O2 | 1.228 (2) | C9—H9B | 0.99 |
N1—C1 | 1.451 (3) | C10—H10A | 0.99 |
C1—C6 | 1.382 (3) | C10—H10B | 0.99 |
C1—C2 | 1.389 (3) | C11—C12 | 1.386 (3) |
N2—O3 | 1.225 (2) | C11—C16 | 1.422 (3) |
N2—O4 | 1.226 (2) | O12—C16 | 1.353 (2) |
N2—C2 | 1.469 (2) | O12—C17 | 1.447 (2) |
C2—C3 | 1.377 (3) | C12—C13 | 1.376 (3) |
N3—O9 | 1.221 (2) | C12—H12 | 0.95 |
N3—O8 | 1.230 (2) | O13—C19 | 1.426 (2) |
N3—C13 | 1.472 (3) | O13—C18 | 1.431 (2) |
C3—C4 | 1.385 (3) | C13—C14 | 1.383 (3) |
C3—H3 | 0.95 | O14—C20 | 1.443 (2) |
N4—O11 | 1.225 (2) | C14—C15 | 1.393 (3) |
N4—O10 | 1.227 (2) | C15—C16 | 1.378 (3) |
N4—C14 | 1.460 (3) | C15—H15 | 0.95 |
C4—O14 | 1.349 (2) | C17—C18 | 1.504 (3) |
C4—C5 | 1.413 (3) | C17—H17A | 0.99 |
O5—C5 | 1.355 (2) | C17—H17B | 0.99 |
O5—C7 | 1.443 (2) | C18—H18A | 0.99 |
N5—C21 | 1.143 (3) | C18—H18B | 0.99 |
C5—C6 | 1.378 (3) | C19—C20 | 1.493 (3) |
O6—C9 | 1.421 (2) | C19—H19A | 0.99 |
O6—C8 | 1.421 (2) | C19—H19B | 0.99 |
C6—H6 | 0.95 | C20—H20A | 0.99 |
O7—C11 | 1.349 (2) | C20—H20B | 0.99 |
O7—C10 | 1.447 (2) | C21—C22 | 1.441 (3) |
C7—C8 | 1.490 (3) | C22—H22A | 0.98 |
C7—H7A | 0.99 | C22—H22B | 0.98 |
C7—H7B | 0.99 | C22—H22C | 0.98 |
C8—H8A | 0.99 | O1W—H1W | 0.839 (10) |
C8—H8B | 0.99 | O1W—H2W | 0.841 (10) |
C9—C10 | 1.484 (3) | | |
| | | |
O1—N1—O2 | 123.82 (18) | C9—C10—H10B | 110.1 |
O1—N1—C1 | 117.59 (16) | H10A—C10—H10B | 108.5 |
O2—N1—C1 | 118.57 (17) | O7—C11—C12 | 124.44 (17) |
C6—C1—C2 | 120.21 (19) | O7—C11—C16 | 116.03 (17) |
C6—C1—N1 | 116.85 (17) | C12—C11—C16 | 119.53 (19) |
C2—C1—N1 | 122.74 (17) | C16—O12—C17 | 116.53 (16) |
O3—N2—O4 | 124.61 (17) | C13—C12—C11 | 120.08 (18) |
O3—N2—C2 | 118.28 (17) | C13—C12—H12 | 120 |
O4—N2—C2 | 117.10 (18) | C11—C12—H12 | 120 |
C3—C2—C1 | 120.24 (17) | C19—O13—C18 | 111.52 (15) |
C3—C2—N2 | 118.30 (17) | C12—C13—C14 | 120.75 (18) |
C1—C2—N2 | 121.23 (18) | C12—C13—N3 | 116.22 (16) |
O9—N3—O8 | 124.85 (17) | C14—C13—N3 | 122.91 (18) |
O9—N3—C13 | 118.77 (17) | C4—O14—C20 | 118.39 (14) |
O8—N3—C13 | 116.35 (18) | C13—C14—C15 | 119.93 (19) |
C2—C3—C4 | 120.34 (17) | C13—C14—N4 | 122.27 (17) |
C2—C3—H3 | 119.8 | C15—C14—N4 | 117.48 (17) |
C4—C3—H3 | 119.8 | C16—C15—C14 | 120.24 (18) |
O11—N4—O10 | 123.91 (19) | C16—C15—H15 | 119.9 |
O11—N4—C14 | 117.85 (17) | C14—C15—H15 | 119.9 |
O10—N4—C14 | 118.22 (17) | O12—C16—C15 | 125.20 (17) |
O14—C4—C3 | 125.32 (17) | O12—C16—C11 | 115.43 (18) |
O14—C4—C5 | 115.48 (16) | C15—C16—C11 | 119.37 (17) |
C3—C4—C5 | 119.20 (18) | O12—C17—C18 | 108.51 (16) |
C5—O5—C7 | 116.27 (15) | O12—C17—H17A | 110 |
O5—C5—C6 | 124.44 (16) | C18—C17—H17A | 110 |
O5—C5—C4 | 115.56 (17) | O12—C17—H17B | 110 |
C6—C5—C4 | 120.00 (17) | C18—C17—H17B | 110 |
C9—O6—C8 | 111.66 (15) | H17A—C17—H17B | 108.4 |
C5—C6—C1 | 120.01 (17) | O13—C18—C17 | 109.43 (16) |
C5—C6—H6 | 120 | O13—C18—H18A | 109.8 |
C1—C6—H6 | 120 | C17—C18—H18A | 109.8 |
C11—O7—C10 | 116.24 (15) | O13—C18—H18B | 109.8 |
O5—C7—C8 | 108.16 (16) | C17—C18—H18B | 109.8 |
O5—C7—H7A | 110.1 | H18A—C18—H18B | 108.2 |
C8—C7—H7A | 110.1 | O13—C19—C20 | 109.41 (16) |
O5—C7—H7B | 110.1 | O13—C19—H19A | 109.8 |
C8—C7—H7B | 110.1 | C20—C19—H19A | 109.8 |
H7A—C7—H7B | 108.4 | O13—C19—H19B | 109.8 |
O6—C8—C7 | 109.27 (17) | C20—C19—H19B | 109.8 |
O6—C8—H8A | 109.8 | H19A—C19—H19B | 108.2 |
C7—C8—H8A | 109.8 | O14—C20—C19 | 107.88 (15) |
O6—C8—H8B | 109.8 | O14—C20—H20A | 110.1 |
C7—C8—H8B | 109.8 | C19—C20—H20A | 110.1 |
H8A—C8—H8B | 108.3 | O14—C20—H20B | 110.1 |
O6—C9—C10 | 108.58 (17) | C19—C20—H20B | 110.1 |
O6—C9—H9A | 110 | H20A—C20—H20B | 108.4 |
C10—C9—H9A | 110 | N5—C21—C22 | 179.5 (3) |
O6—C9—H9B | 110 | C21—C22—H22A | 109.5 |
C10—C9—H9B | 110 | C21—C22—H22B | 109.5 |
H9A—C9—H9B | 108.4 | H22A—C22—H22B | 109.5 |
O7—C10—C9 | 107.83 (16) | C21—C22—H22C | 109.5 |
O7—C10—H10A | 110.1 | H22A—C22—H22C | 109.5 |
C9—C10—H10A | 110.1 | H22B—C22—H22C | 109.5 |
O7—C10—H10B | 110.1 | H1W—O1W—H2W | 97 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O13i | 0.84 (1) | 2.31 (2) | 3.141 (3) | 169 (7) |
O1W—H2W···N5 | 0.84 (1) | 2.11 (2) | 2.932 (3) | 168 (5) |
Symmetry code: (i) −x, −y+1, −z+1. |
Experimental details
Crystal data |
Chemical formula | C20H20N4O14·C2H3N·H2O |
Mr | 599.47 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 10.766 (2), 11.648 (2), 11.813 (2) |
α, β, γ (°) | 69.89 (3), 74.07 (3), 75.84 (3) |
V (Å3) | 1319.0 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.2 × 0.17 × 0.13 |
|
Data collection |
Diffractometer | Nonius Kappa CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25863, 6200, 3503 |
Rint | 0.089 |
(sin θ/λ)max (Å−1) | 0.658 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.119, 1.00 |
No. of reflections | 6200 |
No. of parameters | 388 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.33, −0.32 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O13i | 0.839 (10) | 2.314 (17) | 3.141 (3) | 169 (7) |
O1W—H2W···N5 | 0.841 (10) | 2.105 (16) | 2.932 (3) | 168 (5) |
Symmetry code: (i) −x, −y+1, −z+1. |
The complexation ability of crown ethers has been well studied with regard to alkali metal ions and ammonium derivatized guests (Gokel et al., 2004). Functionalized dibenzocrown ethers offer a versatile means for incorporation into supramolecular constructs, allowing potential applications in artificial photosynthesis and molecular devices to be developed (Langford et al., 2002). We report here the X-ray structure of the tetranitrodibenzocrown ether, (I), an important precursor to a family of antipodally arranged bichromophoric systems.
The synthesis of (I) was achieved using a previously described method (Duggan et al., 2001). Slow evaporation from a mixture of CH3CN and H2O (1:1 (v/v) produced crystals suitable for X-ray analysis. The crystal structure reveals a single crown ether in the asymmetric unit (Figure 1), cocrystallized with one molecule of CH3CN and one of H2O. Both solvent molecules participate in hydrogen bonding; the H2O molecule bridges (I) and CH3CN, with D–A distances of 2.314*(17)*Å and 2.105*(16)*Å, respectively (see Table 1).
Molecules of (I) dimerize in the solid state to form open-ended boxes in which two molecules of H2O and two molecules CH3CN are housed, as shown in Figure 2. Edge-on stacking of (I) forms channels (ca 8 Å wide and 15 Å long) which are filled by the included solvent molecules. The stacking is stabilized by π-π interacts between crown ethers with a mean plane distance of 3.61 Å.