The title compound, C6H16NO3+·C8H5O3-, contains edge-fused R22(12)R22(10)R22(12) motifs involving triethanolammonium and 2-carbonylbenzoate ions. These motifs are connected by C(9) chains with R22(12) rings.
Supporting information
CCDC reference: 633594
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- R factor = 0.066
- wR factor = 0.221
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level B
DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00
_refine_diff_density_max given = 0.913
Test value = 0.800
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 0.91 e/A
Alert level C
DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.67 Sigma
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.76 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.78
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4
PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C8 .. 2.97 Ang.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Triethanolammonium 2-formylbenzoate
top
Crystal data top
C6H16NO3+·C8H5O3− | F(000) = 640 |
Mr = 299.32 | Dx = 1.328 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 17680 reflections |
a = 11.5316 (8) Å | θ = 1.8–27.9° |
b = 7.5990 (4) Å | µ = 0.10 mm−1 |
c = 19.2535 (14) Å | T = 296 K |
β = 117.470 (5)° | Prism, colourless |
V = 1496.93 (17) Å3 | 0.76 × 0.61 × 0.38 mm |
Z = 4 | |
Data collection top
Stoe IPDS II diffractometer | 2947 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long, fine focus | 2283 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.038 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.0° |
ω scans | h = −14→14 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −9→9 |
Tmin = 0.752, Tmax = 0.949 | l = −23→22 |
13959 measured reflections | |
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)] = 0.066 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.221 | w = 1/[σ2(Fo2) + (0.128P)2 + 0.5183P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
2947 reflections | Δρmax = 0.91 e Å−3 |
203 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.008 (3) |
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 of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.1997 (2) | 0.4987 (4) | 0.55067 (14) | 0.0476 (6) | |
C2 | 0.1498 (2) | 0.6299 (3) | 0.58968 (15) | 0.0452 (6) | |
C3 | 0.1617 (3) | 0.8079 (4) | 0.5764 (2) | 0.0700 (9) | |
H3 | 0.1913 | 0.8409 | 0.5408 | 0.084* | |
C4 | 0.1302 (3) | 0.9339 (4) | 0.6153 (3) | 0.0898 (13) | |
H4 | 0.1397 | 1.0521 | 0.6065 | 0.108* | |
C5 | 0.0845 (3) | 0.8880 (4) | 0.6678 (2) | 0.0779 (10) | |
H5 | 0.0641 | 0.9745 | 0.6946 | 0.094* | |
C6 | 0.0695 (3) | 0.7136 (4) | 0.67988 (17) | 0.0610 (7) | |
H6 | 0.0377 | 0.6821 | 0.7146 | 0.073* | |
C7 | 0.1010 (2) | 0.5839 (3) | 0.64118 (13) | 0.0439 (6) | |
C8 | 0.0703 (3) | 0.3991 (4) | 0.65060 (17) | 0.0546 (7) | |
H7 | 0.0615 | 0.3187 | 0.6121 | 0.065* | |
C9 | 0.3299 (3) | 0.4015 (4) | 0.8961 (2) | 0.0692 (8) | |
H9A | 0.3944 | 0.4949 | 0.9134 | 0.083* | |
H9B | 0.2645 | 0.4280 | 0.8431 | 0.083* | |
C10 | 0.2677 (3) | 0.3945 (4) | 0.94728 (18) | 0.0639 (7) | |
H10A | 0.2261 | 0.5064 | 0.9458 | 0.077* | |
H10B | 0.2010 | 0.3038 | 0.9291 | 0.077* | |
C11 | 0.4992 (3) | 0.2641 (5) | 0.87255 (17) | 0.0699 (9) | |
H11A | 0.5438 | 0.1551 | 0.8737 | 0.084* | |
H11B | 0.5630 | 0.3421 | 0.9112 | 0.084* | |
C12 | 0.4531 (4) | 0.3464 (6) | 0.7931 (2) | 0.0878 (12) | |
H12A | 0.3992 | 0.4480 | 0.7886 | 0.105* | |
H12B | 0.5280 | 0.3864 | 0.7872 | 0.105* | |
C13 | 0.3010 (3) | 0.0893 (4) | 0.85297 (17) | 0.0636 (8) | |
H13A | 0.2759 | 0.1025 | 0.7977 | 0.076* | |
H13B | 0.2234 | 0.1063 | 0.8597 | 0.076* | |
C14 | 0.3523 (3) | −0.0979 (4) | 0.87857 (17) | 0.0662 (8) | |
H14A | 0.2864 | −0.1814 | 0.8453 | 0.079* | |
H14B | 0.4294 | −0.1155 | 0.8714 | 0.079* | |
N1 | 0.3965 (2) | 0.2251 (3) | 0.89689 (13) | 0.0528 (6) | |
O1 | 0.2530 (2) | 0.3620 (3) | 0.58843 (11) | 0.0645 (6) | |
O2 | 0.1891 (2) | 0.5370 (3) | 0.48535 (11) | 0.0687 (6) | |
O3 | 0.0562 (3) | 0.3472 (4) | 0.70469 (16) | 0.0915 (8) | |
O4 | 0.3618 (2) | 0.3577 (3) | 1.02424 (12) | 0.0631 (6) | |
O5 | 0.3833 (3) | 0.2300 (4) | 0.73526 (15) | 0.0964 (9) | |
O6 | 0.3843 (2) | −0.1322 (3) | 0.95732 (11) | 0.0617 (6) | |
H1 | 0.443 (3) | 0.195 (4) | 0.946 (2) | 0.067 (9)* | |
H4A | 0.330 (3) | 0.289 (5) | 1.043 (2) | 0.068 (10)* | |
H5A | 0.341 (5) | 0.281 (6) | 0.687 (3) | 0.115 (15)* | |
H6A | 0.321 (5) | −0.117 (6) | 0.967 (3) | 0.122 (17)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0448 (12) | 0.0609 (15) | 0.0411 (13) | 0.0017 (10) | 0.0234 (10) | 0.0043 (10) |
C2 | 0.0421 (11) | 0.0438 (12) | 0.0500 (13) | 0.0015 (9) | 0.0215 (10) | 0.0049 (10) |
C3 | 0.0671 (17) | 0.0504 (15) | 0.101 (3) | 0.0005 (13) | 0.0456 (18) | 0.0143 (15) |
C4 | 0.074 (2) | 0.0396 (14) | 0.149 (4) | −0.0026 (14) | 0.046 (2) | −0.0083 (18) |
C5 | 0.0591 (17) | 0.0625 (19) | 0.100 (3) | 0.0030 (14) | 0.0267 (18) | −0.0323 (18) |
C6 | 0.0480 (14) | 0.0758 (19) | 0.0585 (16) | 0.0045 (13) | 0.0240 (12) | −0.0159 (14) |
C7 | 0.0400 (11) | 0.0509 (13) | 0.0414 (12) | 0.0029 (9) | 0.0192 (10) | −0.0007 (10) |
C8 | 0.0568 (14) | 0.0577 (15) | 0.0606 (16) | 0.0077 (11) | 0.0368 (13) | 0.0131 (12) |
C9 | 0.084 (2) | 0.0536 (16) | 0.0636 (18) | 0.0019 (14) | 0.0285 (16) | 0.0036 (13) |
C10 | 0.0654 (17) | 0.0564 (16) | 0.0664 (18) | 0.0024 (13) | 0.0274 (15) | −0.0037 (13) |
C11 | 0.0557 (15) | 0.103 (2) | 0.0479 (15) | −0.0151 (15) | 0.0210 (13) | 0.0089 (15) |
C12 | 0.101 (3) | 0.103 (3) | 0.059 (2) | −0.027 (2) | 0.0365 (19) | 0.0124 (19) |
C13 | 0.0689 (17) | 0.0642 (17) | 0.0505 (15) | −0.0041 (13) | 0.0215 (13) | 0.0011 (12) |
C14 | 0.084 (2) | 0.0700 (18) | 0.0472 (15) | 0.0183 (15) | 0.0321 (15) | 0.0017 (13) |
N1 | 0.0475 (11) | 0.0728 (15) | 0.0352 (11) | −0.0016 (10) | 0.0166 (9) | 0.0051 (10) |
O1 | 0.0785 (13) | 0.0695 (13) | 0.0512 (11) | 0.0280 (10) | 0.0348 (10) | 0.0089 (9) |
O2 | 0.0699 (12) | 0.0971 (16) | 0.0493 (11) | 0.0046 (11) | 0.0361 (10) | 0.0120 (10) |
O3 | 0.120 (2) | 0.0945 (18) | 0.0874 (18) | 0.0052 (15) | 0.0710 (17) | 0.0307 (14) |
O4 | 0.0655 (12) | 0.0691 (13) | 0.0563 (12) | −0.0178 (10) | 0.0295 (10) | −0.0031 (9) |
O5 | 0.123 (2) | 0.108 (2) | 0.0506 (14) | −0.0071 (17) | 0.0343 (15) | 0.0109 (13) |
O6 | 0.0566 (11) | 0.0833 (14) | 0.0455 (10) | 0.0085 (10) | 0.0238 (9) | 0.0129 (9) |
Geometric parameters (Å, º) top
C1—O2 | 1.241 (3) | C10—H10A | 0.9700 |
C1—O1 | 1.254 (3) | C10—H10B | 0.9700 |
C1—C2 | 1.513 (3) | C11—N1 | 1.490 (4) |
C2—C7 | 1.392 (3) | C11—C12 | 1.505 (4) |
C2—C3 | 1.395 (4) | C11—H11A | 0.9700 |
C3—C4 | 1.364 (5) | C11—H11B | 0.9700 |
C3—H3 | 0.9300 | C12—O5 | 1.357 (5) |
C4—C5 | 1.383 (6) | C12—H12A | 0.9700 |
C4—H4 | 0.9300 | C12—H12B | 0.9700 |
C5—C6 | 1.370 (5) | C13—N1 | 1.461 (4) |
C5—H5 | 0.9300 | C13—C14 | 1.532 (4) |
C6—C7 | 1.381 (4) | C13—H13A | 0.9700 |
C6—H6 | 0.9300 | C13—H13B | 0.9700 |
C7—C8 | 1.479 (4) | C14—O6 | 1.410 (3) |
C8—O3 | 1.193 (3) | C14—H14A | 0.9700 |
C8—H7 | 0.9300 | C14—H14B | 0.9700 |
C9—C10 | 1.462 (5) | N1—H1 | 0.88 (4) |
C9—N1 | 1.542 (4) | O4—H4A | 0.82 (4) |
C9—H9A | 0.9700 | O5—H5A | 0.92 (5) |
C9—H9B | 0.9700 | O6—H6A | 0.84 (5) |
C10—O4 | 1.403 (4) | | |
| | | |
O2—C1—O1 | 125.1 (2) | H10A—C10—H10B | 108.2 |
O2—C1—C2 | 117.8 (2) | N1—C11—C12 | 116.3 (3) |
O1—C1—C2 | 117.0 (2) | N1—C11—H11A | 108.2 |
C7—C2—C3 | 118.7 (2) | C12—C11—H11A | 108.2 |
C7—C2—C1 | 124.1 (2) | N1—C11—H11B | 108.2 |
C3—C2—C1 | 117.2 (2) | C12—C11—H11B | 108.2 |
C4—C3—C2 | 120.5 (3) | H11A—C11—H11B | 107.4 |
C4—C3—H3 | 119.8 | O5—C12—C11 | 111.2 (3) |
C2—C3—H3 | 119.8 | O5—C12—H12A | 109.4 |
C3—C4—C5 | 120.8 (3) | C11—C12—H12A | 109.4 |
C3—C4—H4 | 119.6 | O5—C12—H12B | 109.4 |
C5—C4—H4 | 119.6 | C11—C12—H12B | 109.4 |
C6—C5—C4 | 119.3 (3) | H12A—C12—H12B | 108.0 |
C6—C5—H5 | 120.4 | N1—C13—C14 | 113.2 (2) |
C4—C5—H5 | 120.4 | N1—C13—H13A | 108.9 |
C5—C6—C7 | 120.9 (3) | C14—C13—H13A | 108.9 |
C5—C6—H6 | 119.6 | N1—C13—H13B | 108.9 |
C7—C6—H6 | 119.6 | C14—C13—H13B | 108.9 |
C6—C7—C2 | 119.9 (2) | H13A—C13—H13B | 107.8 |
C6—C7—C8 | 118.3 (2) | O6—C14—C13 | 112.8 (2) |
C2—C7—C8 | 121.6 (2) | O6—C14—H14A | 109.0 |
O3—C8—C7 | 123.9 (3) | C13—C14—H14A | 109.0 |
O3—C8—H7 | 118.1 | O6—C14—H14B | 109.0 |
C7—C8—H7 | 118.1 | C13—C14—H14B | 109.0 |
C10—C9—N1 | 111.1 (2) | H14A—C14—H14B | 107.8 |
C10—C9—H9A | 109.4 | C13—N1—C11 | 117.1 (2) |
N1—C9—H9A | 109.4 | C13—N1—C9 | 111.6 (2) |
C10—C9—H9B | 109.4 | C11—N1—C9 | 106.8 (2) |
N1—C9—H9B | 109.4 | C13—N1—H1 | 111 (2) |
H9A—C9—H9B | 108.0 | C11—N1—H1 | 103 (2) |
O4—C10—C9 | 109.7 (3) | C9—N1—H1 | 107 (2) |
O4—C10—H10A | 109.7 | C10—O4—H4A | 108 (2) |
C9—C10—H10A | 109.7 | C12—O5—H5A | 113 (3) |
O4—C10—H10B | 109.7 | C14—O6—H6A | 113 (3) |
C9—C10—H10B | 109.7 | | |
| | | |
O2—C1—C2—C7 | 150.3 (2) | C3—C2—C7—C8 | 172.3 (3) |
O1—C1—C2—C7 | −32.2 (3) | C1—C2—C7—C8 | −11.9 (4) |
O2—C1—C2—C3 | −33.8 (4) | C6—C7—C8—O3 | −22.6 (4) |
O1—C1—C2—C3 | 143.7 (3) | C2—C7—C8—O3 | 162.9 (3) |
C7—C2—C3—C4 | 2.2 (5) | N1—C9—C10—O4 | 59.6 (3) |
C1—C2—C3—C4 | −173.9 (3) | N1—C11—C12—O5 | −69.8 (5) |
C2—C3—C4—C5 | −0.8 (6) | N1—C13—C14—O6 | 62.0 (4) |
C3—C4—C5—C6 | −0.7 (6) | C14—C13—N1—C11 | 80.3 (3) |
C4—C5—C6—C7 | 0.8 (5) | C14—C13—N1—C9 | −156.2 (3) |
C5—C6—C7—C2 | 0.6 (4) | C12—C11—N1—C13 | 66.8 (4) |
C5—C6—C7—C8 | −174.0 (3) | C12—C11—N1—C9 | −59.2 (4) |
C3—C2—C7—C6 | −2.1 (4) | C10—C9—N1—C13 | 73.8 (3) |
C1—C2—C7—C6 | 173.7 (2) | C10—C9—N1—C11 | −157.0 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O6i | 0.88 (4) | 2.06 (3) | 2.867 (3) | 153 (3) |
O4—H4A···O1ii | 0.82 (4) | 1.88 (4) | 2.706 (3) | 178 (3) |
O5—H5A···O1 | 0.92 (5) | 1.79 (5) | 2.709 (3) | 175 (5) |
O6—H6A···O2ii | 0.84 (5) | 1.82 (5) | 2.645 (3) | 168 (5) |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x, −y+1/2, z+1/2. |