A 2:1:1 2-(2-carboxy­phenyl­amino)­isophthalic acid–ethyl acetate–butan-2-one inclusion complex

Móczár, I.; Huszthy, P.; Báthori, N.; Czugler, M.

doi:10.1107/S1600536804012401

A 2:1:1 2-(2-carboxyphenylamino)isophthalic acid-ethyl acetate-butan-2-one inclusion complex

I. Móczár, P. Huszthy, N. Báthori and M. Czugler

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804012401/cf6352sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804012401/cf6352Isup2.hkl Contains datablock I

CCDC reference: 242348

checkCIF report

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

Computing details top

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.

(I) top

Crystal data top

C₁₅H₁₁NO₆·0.5C₄H₈O₂·0.5C₄H₈O	F(000) = 800
M_r = 381.35	D_x = 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	R_int = 0.012
Radiation source: fine-focus sealed tube	θ_max = 75.7°, θ_min = 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(F_o²) + (0.1071P)² + 0.2617P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
3834 reflections	Δρ_max = 0.44 e Å⁻³
281 parameters	Δρ_min = −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	U_iso*/U_eq	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.

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A 2:1:1 2-(2-carboxy­phenyl­amino)­isophthalic acid-ethyl acetate-butan-2-one inclusion complex

Supporting information

Key indicators

checkCIF/PLATON results

A 2:1:1 2-(2-carboxyphenylamino)isophthalic acid-ethyl acetate-butan-2-one inclusion complex