In the title compound, C15H11NO6·0.5C4H8O2·0.5C4H8O, extensive hydrogen bonding establishes a rigid host matrix in which a disordered mixture of ethyl acetate and butan-2-one solvent molecules is held.
Supporting information
CCDC reference: 242348
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- H-atom completeness 58%
- R factor = 0.052
- wR factor = 0.167
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT773_ALERT_2_A Suspect C-C Bond in CIF: C1L' -C2L' .. 1.87 Ang.
Alert level C
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
calculated from the _atom_site* data lies outside
the range 0.99 <> 1.01
From the CIF: _cell_formula_units_Z 4
From the CIF: _chemical_formula_weight 381.35
TEST: Calculate formula weight from _atom_site_*
atom mass num sum
C 12.01 19.00 228.21
H 1.01 11.00 11.09
N 14.01 1.00 14.01
O 16.00 7.50 119.99
Calculated formula weight 373.30
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT043_ALERT_1_C Check Reported Molecular Weight ................ 381.35
PLAT044_ALERT_1_C Calculated and Reported Dx Differ .............. ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.05
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O7
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C2L
PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
Alert level G
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C19 H19 N1 O7.5
Atom count from the _atom_site data: C19 H11 N1 O7.5
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 4
From the CIF: _chemical_formula_sum C19 H19 N O7.50
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 76.00 76.00 0.00
H 76.00 44.00 32.00
N 4.00 4.00 0.00
O 30.00 30.00 0.00
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
13 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: Locally modified CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: XCAD4 (Harms, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
Crystal data top
C15H11NO6·0.5C4H8O2·0.5C4H8O | F(000) = 800 |
Mr = 381.35 | Dx = 1.327 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 7.487 (1) Å | θ = 37.0–39.8° |
b = 16.444 (1) Å | µ = 0.88 mm−1 |
c = 15.748 (1) Å | T = 295 K |
β = 100.21 (1)° | Prism, colourless |
V = 1908.1 (3) Å3 | 0.56 × 0.55 × 0.43 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.012 |
Radiation source: fine-focus sealed tube | θmax = 75.7°, θmin = 3.9° |
Graphite monochromator | h = −9→9 |
ω–2θ' scans | k = 0→20 |
4100 measured reflections | l = 0→19 |
3834 independent reflections | 3 standard reflections every 100 reflections |
3372 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.167 | w = 1/[σ2(Fo2) + (0.1071P)2 + 0.2617P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
3834 reflections | Δρmax = 0.44 e Å−3 |
281 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0052 (8) |
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. Refinement on F2 for all reflections except those 135 that were flagged
and omitted for suspected systematic errors. Presence of some systematic
absence violations together with the extensive guest disorder are signs of a
possible incommensurate lattice for guests placed in paralell channels with
the c axis of the obiously robust host matrix. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.3655 (2) | 0.54119 (8) | 0.65867 (8) | 0.0680 (4) | |
O2 | 0.19749 (19) | 0.51656 (8) | 0.53058 (8) | 0.0641 (4) | |
H2O | 0.1605 | 0.5664 | 0.5315 | 0.076* | |
O3 | 0.5550 (3) | 0.25271 (10) | 0.81545 (8) | 0.0826 (5) | |
O4 | 0.5553 (3) | 0.15380 (9) | 0.71942 (10) | 0.0922 (6) | |
H4O | 0.6197 | 0.1332 | 0.7751 | 0.167* | |
O5 | 0.2677 (2) | 0.52278 (13) | 0.96225 (10) | 0.0951 (6) | |
H5O | 0.3569 | 0.5395 | 0.9968 | 0.098* | |
O6 | 0.46168 (18) | 0.44317 (10) | 0.91058 (8) | 0.0738 (4) | |
N1 | 0.35849 (17) | 0.38556 (8) | 0.74843 (7) | 0.0458 (3) | |
H1N | 0.4315 | 0.3765 | 0.8058 | 0.060* | |
C1 | 0.40807 (18) | 0.36064 (9) | 0.67138 (8) | 0.0400 (3) | |
C2 | 0.4922 (2) | 0.28487 (10) | 0.66525 (9) | 0.0478 (4) | |
C3 | 0.5373 (3) | 0.25993 (11) | 0.58709 (11) | 0.0581 (4) | |
H3 | 0.5945 | 0.2101 | 0.5842 | 0.076* | |
C4 | 0.4990 (3) | 0.30749 (12) | 0.51414 (10) | 0.0590 (4) | |
H4 | 0.5278 | 0.2897 | 0.4622 | 0.077* | |
C5 | 0.4173 (2) | 0.38187 (10) | 0.51945 (9) | 0.0490 (4) | |
H5 | 0.3894 | 0.4140 | 0.4703 | 0.064* | |
C6 | 0.37575 (18) | 0.40977 (8) | 0.59694 (8) | 0.0409 (3) | |
C7 | 0.18943 (19) | 0.41666 (9) | 0.75586 (8) | 0.0423 (3) | |
C8 | 0.0396 (2) | 0.40655 (10) | 0.68918 (10) | 0.0507 (4) | |
H8 | 0.0555 | 0.3807 | 0.6385 | 0.066* | |
C9 | −0.1310 (2) | 0.43417 (13) | 0.69719 (12) | 0.0607 (4) | |
H9 | −0.2275 | 0.4273 | 0.6517 | 0.079* | |
C10 | −0.1598 (2) | 0.47184 (15) | 0.77191 (14) | 0.0679 (5) | |
H10 | −0.2754 | 0.4889 | 0.7777 | 0.088* | |
C11 | −0.0150 (3) | 0.48366 (14) | 0.83758 (12) | 0.0643 (5) | |
H11 | −0.0338 | 0.5099 | 0.8876 | 0.084* | |
C12 | 0.1610 (2) | 0.45718 (10) | 0.83145 (9) | 0.0493 (4) | |
C13 | 0.5371 (3) | 0.23059 (11) | 0.74172 (11) | 0.0590 (4) | |
C14 | 0.3115 (2) | 0.49568 (9) | 0.60016 (10) | 0.0461 (3) | |
C15 | 0.3093 (2) | 0.47301 (12) | 0.90409 (10) | 0.0573 (4) | |
C1L | 1.0424 (6) | 0.1659 (3) | 0.8302 (3) | 0.1251 (12) | |
C2L | 1.0002 (8) | 0.2039 (4) | 0.9041 (5) | 0.0812 (14) | 0.50 |
O7 | 0.9330 (3) | 0.16624 (11) | 0.97365 (16) | 0.1065 (7) | |
C3L | 1.0207 (9) | 0.2857 (3) | 0.9143 (4) | 0.0830 (16) | 0.50 |
C4L | 0.9551 (11) | 0.3204 (3) | 0.9875 (5) | 0.0985 (19) | 0.50 |
C1L' | 1.0598 (14) | 0.3118 (4) | 1.0434 (8) | 0.137 (3) | 0.50 |
C2L' | 0.9920 (7) | 0.2308 (3) | 0.9608 (5) | 0.0851 (14) | 0.50 |
O3L' | 1.0378 (8) | 0.2449 (4) | 0.8876 (4) | 0.1088 (18) | 0.50 |
C5L' | 1.0461 (17) | 0.1921 (5) | 0.7446 (8) | 0.160 (4) | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0880 (10) | 0.0489 (6) | 0.0608 (8) | −0.0051 (6) | −0.0039 (6) | −0.0107 (5) |
O2 | 0.0710 (8) | 0.0551 (6) | 0.0587 (7) | 0.0108 (5) | −0.0092 (6) | 0.0024 (5) |
O3 | 0.1230 (13) | 0.0832 (10) | 0.0410 (7) | 0.0346 (9) | 0.0128 (7) | 0.0135 (6) |
O4 | 0.1538 (17) | 0.0618 (8) | 0.0609 (8) | 0.0351 (9) | 0.0186 (9) | 0.0141 (6) |
O5 | 0.0697 (9) | 0.1452 (15) | 0.0633 (8) | 0.0351 (9) | −0.0077 (7) | −0.0541 (9) |
O6 | 0.0597 (7) | 0.1094 (11) | 0.0465 (6) | 0.0255 (7) | −0.0064 (5) | −0.0280 (6) |
N1 | 0.0472 (6) | 0.0594 (7) | 0.0291 (5) | 0.0078 (5) | 0.0024 (4) | −0.0040 (5) |
C1 | 0.0398 (6) | 0.0486 (7) | 0.0304 (6) | −0.0012 (5) | 0.0030 (5) | −0.0022 (5) |
C2 | 0.0532 (8) | 0.0527 (8) | 0.0377 (7) | 0.0067 (6) | 0.0083 (6) | 0.0027 (6) |
C3 | 0.0707 (10) | 0.0588 (9) | 0.0463 (8) | 0.0153 (8) | 0.0148 (7) | −0.0027 (7) |
C4 | 0.0730 (11) | 0.0702 (10) | 0.0366 (7) | 0.0078 (8) | 0.0174 (7) | −0.0044 (7) |
C5 | 0.0550 (8) | 0.0590 (9) | 0.0323 (6) | −0.0025 (6) | 0.0060 (6) | 0.0032 (6) |
C6 | 0.0409 (6) | 0.0459 (7) | 0.0344 (6) | −0.0037 (5) | 0.0028 (5) | 0.0000 (5) |
C7 | 0.0440 (7) | 0.0474 (7) | 0.0355 (6) | −0.0019 (5) | 0.0072 (5) | −0.0002 (5) |
C8 | 0.0466 (8) | 0.0636 (9) | 0.0415 (7) | −0.0080 (6) | 0.0070 (6) | −0.0046 (6) |
C9 | 0.0414 (7) | 0.0834 (12) | 0.0548 (9) | −0.0094 (7) | 0.0019 (6) | 0.0002 (8) |
C10 | 0.0425 (8) | 0.0924 (13) | 0.0701 (11) | 0.0045 (8) | 0.0134 (8) | −0.0043 (10) |
C11 | 0.0524 (9) | 0.0865 (13) | 0.0560 (9) | 0.0083 (8) | 0.0150 (7) | −0.0112 (9) |
C12 | 0.0474 (8) | 0.0620 (9) | 0.0384 (7) | 0.0039 (6) | 0.0074 (6) | −0.0050 (6) |
C13 | 0.0712 (10) | 0.0620 (9) | 0.0452 (8) | 0.0178 (8) | 0.0136 (7) | 0.0100 (7) |
C14 | 0.0474 (7) | 0.0454 (7) | 0.0441 (7) | −0.0052 (6) | 0.0042 (6) | 0.0014 (6) |
C15 | 0.0554 (9) | 0.0779 (11) | 0.0377 (7) | 0.0118 (8) | 0.0058 (6) | −0.0142 (7) |
C1L | 0.155 (3) | 0.113 (2) | 0.101 (2) | 0.006 (2) | 0.005 (2) | −0.0173 (19) |
C2L | 0.073 (3) | 0.082 (4) | 0.083 (3) | 0.017 (3) | 0.001 (2) | −0.014 (3) |
O7 | 0.1018 (13) | 0.0658 (10) | 0.1439 (18) | −0.0186 (9) | 0.0000 (12) | 0.0168 (10) |
C3L | 0.111 (4) | 0.042 (2) | 0.110 (4) | 0.001 (2) | 0.056 (3) | −0.003 (2) |
C4L | 0.133 (5) | 0.059 (3) | 0.123 (5) | −0.002 (3) | 0.076 (4) | −0.009 (3) |
C1L' | 0.137 (7) | 0.073 (4) | 0.201 (10) | 0.031 (4) | 0.028 (6) | 0.023 (5) |
C2L' | 0.073 (3) | 0.058 (2) | 0.122 (5) | 0.0047 (19) | 0.010 (3) | 0.014 (3) |
O3L' | 0.130 (4) | 0.083 (3) | 0.121 (4) | −0.018 (3) | 0.039 (3) | 0.029 (3) |
C5L' | 0.211 (11) | 0.105 (5) | 0.176 (10) | −0.011 (6) | 0.066 (8) | 0.008 (6) |
Geometric parameters (Å, º) top
O1—C14 | 1.2002 (19) | C6—C14 | 1.496 (2) |
O2—C14 | 1.310 (2) | C7—C8 | 1.404 (2) |
O2—H2O | 0.867 | C7—C12 | 1.413 (2) |
O3—C13 | 1.201 (2) | C8—C9 | 1.382 (2) |
O4—C13 | 1.324 (2) | C8—H8 | 0.930 |
O4—H4O | 0.983 | C9—C10 | 1.380 (3) |
O5—C15 | 1.306 (2) | C9—H9 | 0.930 |
O5—H5O | 0.829 | C10—C11 | 1.373 (3) |
O6—C15 | 1.229 (2) | C10—H10 | 0.930 |
N1—C7 | 1.3892 (19) | C11—C12 | 1.407 (2) |
N1—C1 | 1.3921 (17) | C11—H11 | 0.930 |
N1—H1N | 0.981 | C12—C15 | 1.470 (2) |
C1—C2 | 1.407 (2) | C1L—C2L | 1.406 (8) |
C1—C6 | 1.4089 (19) | C1L—C5L' | 1.420 (12) |
C2—C3 | 1.394 (2) | C1L—O3L' | 1.587 (8) |
C2—C13 | 1.489 (2) | C2L—C3L | 1.359 (8) |
C3—C4 | 1.377 (2) | C2L—O7 | 1.425 (9) |
C3—H3 | 0.930 | O7—C2L' | 1.181 (5) |
C4—C5 | 1.377 (3) | C3L—C4L | 1.448 (7) |
C4—H4 | 0.930 | C1L'—C2L' | 1.867 (14) |
C5—C6 | 1.390 (2) | C2L'—O3L' | 1.281 (9) |
C5—H5 | 0.930 | | |
| | | |
C14—O2—H2O | 113.4 | C10—C9—C8 | 120.78 (15) |
C13—O4—H4O | 98.6 | C10—C9—H9 | 119.6 |
C15—O5—H5O | 113.7 | C8—C9—H9 | 119.6 |
C7—N1—C1 | 124.72 (11) | C11—C10—C9 | 118.95 (16) |
C7—N1—H1N | 110.2 | C11—C10—H10 | 120.5 |
C1—N1—H1N | 124.6 | C9—C10—H10 | 120.5 |
N1—C1—C2 | 120.81 (12) | C10—C11—C12 | 121.90 (16) |
N1—C1—C6 | 121.57 (13) | C10—C11—H11 | 119.1 |
C2—C1—C6 | 117.62 (12) | C12—C11—H11 | 119.1 |
C3—C2—C1 | 120.15 (14) | C11—C12—C7 | 119.12 (15) |
C3—C2—C13 | 118.84 (14) | C11—C12—C15 | 118.65 (14) |
C1—C2—C13 | 121.00 (13) | C7—C12—C15 | 122.23 (14) |
C4—C3—C2 | 121.47 (15) | O3—C13—O4 | 123.09 (16) |
C4—C3—H3 | 119.3 | O3—C13—C2 | 124.80 (17) |
C2—C3—H3 | 119.3 | O4—C13—C2 | 112.12 (15) |
C5—C4—C3 | 118.87 (14) | O1—C14—O2 | 124.03 (15) |
C5—C4—H4 | 120.6 | O1—C14—C6 | 123.25 (14) |
C3—C4—H4 | 120.6 | O2—C14—C6 | 112.64 (13) |
C4—C5—C6 | 121.19 (14) | O6—C15—O5 | 121.66 (15) |
C4—C5—H5 | 119.4 | O6—C15—C12 | 123.79 (14) |
C6—C5—H5 | 119.4 | O5—C15—C12 | 114.54 (15) |
C5—C6—C1 | 120.60 (13) | C5L'—C1L—O3L' | 107.4 (5) |
C5—C6—C14 | 117.71 (12) | C3L—C2L—C1L | 120.0 (7) |
C1—C6—C14 | 121.47 (12) | C3L—C2L—O7 | 112.8 (5) |
N1—C7—C8 | 120.83 (13) | C1L—C2L—O7 | 127.2 (5) |
N1—C7—C12 | 121.35 (13) | C2L—C3L—C4L | 115.8 (5) |
C8—C7—C12 | 117.79 (13) | O7—C2L'—O3L' | 118.9 (7) |
C9—C8—C7 | 121.44 (14) | O7—C2L'—C1L' | 125.9 (6) |
C9—C8—H8 | 119.3 | O3L'—C2L'—C1L' | 114.5 (5) |
C7—C8—H8 | 119.3 | C2L'—O3L'—C1L | 113.7 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···O7i | 0.87 | 1.78 | 2.645 (2) | 175 |
O4—H4O···O1ii | 0.98 | 1.83 | 2.6576 (18) | 140 |
O5—H5O···O6iii | 0.83 | 1.83 | 2.6441 (19) | 166 |
N1—H1N···O6 | 0.98 | 1.96 | 2.7047 (16) | 131 |
N1—H1N···O3 | 0.98 | 2.23 | 2.7388 (19) | 111 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+2. |