Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.054
- wR factor = 0.154
- Data-to-parameter ratio = 10.9
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT432_ALERT_2_A Short Inter X...Y Contact C4A .. C5B = 2.78 Ang.
| Author Response: The phenyl group is disordered. The carbon atoms with suffix
A,
B and C belong to different components of the disordered phenyl group.
|
PLAT432_ALERT_2_A Short Inter X...Y Contact C5A .. C4B = 2.75 Ang.
| Author Response: The phenyl group is disordered. The carbon atoms with suffix
A,
B and C belong to different components of the disordered phenyl group.
|
PLAT432_ALERT_2_A Short Inter X...Y Contact C5A .. C5B = 2.77 Ang.
| Author Response: The phenyl group is disordered. The carbon atoms with suffix
A,
B and C belong to different components of the disordered phenyl group.
|
Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ..... = 6
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.68 Ratio
PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... C5B
PLAT432_ALERT_2_B Short Inter X...Y Contact C4B .. C5B = 2.98 Ang.
| Author Response: The phenyl group is disordered. The carbon atoms with suffix
A,
B and C belong to different components of the disordered phenyl group.
|
PLAT432_ALERT_2_B Short Inter X...Y Contact C5B .. C5B = 3.01 Ang.
| Author Response: The phenyl group is disordered. The carbon atoms with suffix
A,
B and C belong to different components of the disordered phenyl group.
|
PLAT432_ALERT_2_B Short Inter X...Y Contact C5B .. C5B = 3.01 Ang.
| Author Response: The phenyl group is disordered. The carbon atoms with suffix
A,
B and C belong to different components of the disordered phenyl group.
|
PLAT432_ALERT_2_B Short Inter X...Y Contact C7B .. C7B = 2.92 Ang.
| Author Response: The phenyl group is disordered. The carbon atoms with suffix
A,
B and C belong to different components of the disordered phenyl group.
|
Alert level C
PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 18
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.58 Ratio
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C4C
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C5C
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C7C
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C8B
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C3B
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C6B
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C6C
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.29
PLAT301_ALERT_3_C Main Residue Disorder ......................... 21.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT432_ALERT_2_C Short Inter X...Y Contact C4B .. C5B = 3.15 Ang.
| Author Response: The phenyl group is disordered. The carbon atoms with suffix
A,
B and C belong to different components of the disordered phenyl group.
|
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 9.20 Deg.
C3C -C2 -C3A 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 10.20 Deg.
C3C -C2 -C3B 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 1.50 Deg.
C3A -C2 -C3B 1.555 1.555 1.555
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.50
From the CIF: _reflns_number_total 1484
Count of symmetry unique reflns 1482
Completeness (_total/calc) 100.13%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2
Fraction of Friedel pairs measured 0.001
Are heavy atom types Z>Si present no
3 ALERT level A = In general: serious problem
7 ALERT level B = Potentially serious problem
16 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
22 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1985); program(s) used to solve structure: SIR2 (Altomare et al., 1993); 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).
Crystal data top
C8H8O3·C3H7NO2 | F(000) = 512 |
Mr = 241.24 | Dx = 1.366 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 20 reflections |
a = 17.795 (4) Å | θ = 5.5–9.8° |
b = 5.394 (2) Å | µ = 0.11 mm−1 |
c = 12.431 (2) Å | T = 295 K |
β = 100.65 (1)° | Prism, colorless |
V = 1172.7 (5) Å3 | 0.4 × 0.4 × 0.2 mm |
Z = 4 | |
Data collection top
Rigaku AFC-7S diffractometer | Rint = 0.017 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 1.7° |
Graphite monochromator | h = −1→22 |
ω/2θ scans | k = −7→1 |
1928 measured reflections | l = −16→15 |
1484 independent reflections | 3 standard reflections every 150 reflections |
1276 reflections with I > 2σ(I) | intensity decay: 0.6% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0812P)2 + 1.03P] where P = (Fo2 + 2Fc2)/3 |
1484 reflections | (Δ/σ)max = 0.001 |
136 parameters | Δρmax = 0.35 e Å−3 |
1 restraint | Δρmin = −0.33 e Å−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 | Occ. (<1) |
O1 | 0.71606 (13) | 0.2376 (5) | 0.1896 (2) | 0.0459 (6) | |
H1A | 0.7121 | 0.0861 | 0.1878 | 0.055* | |
O2 | 0.57574 (13) | 0.7041 (5) | 0.1353 (2) | 0.0470 (6) | |
H2A | 0.5431 | 0.5991 | 0.1395 | 0.056* | |
O3 | 0.70046 (13) | 0.7252 (5) | 0.1586 (2) | 0.0424 (6) | |
C1 | 0.64173 (18) | 0.6087 (6) | 0.1633 (3) | 0.0323 (7) | |
C2 | 0.64601 (18) | 0.3442 (6) | 0.2061 (3) | 0.0336 (7) | |
H2 | 0.6029 | 0.2479 | 0.1665 | 0.040* | |
C3A | 0.6438 (4) | 0.3447 (14) | 0.3296 (4) | 0.0396 (10)* | 0.52 |
C4A | 0.6829 (4) | 0.5255 (12) | 0.3975 (5) | 0.0489 (17)* | 0.52 |
H4A | 0.7097 | 0.6488 | 0.3684 | 0.059* | 0.52 |
C5A | 0.6820 (4) | 0.5220 (13) | 0.5091 (4) | 0.062 (2)* | 0.52 |
H5A | 0.7082 | 0.6430 | 0.5545 | 0.074* | 0.52 |
C6A | 0.6420 (5) | 0.3377 (16) | 0.5527 (4) | 0.067 (4)* | 0.52 |
H6A | 0.6414 | 0.3353 | 0.6273 | 0.081* | 0.52 |
C7A | 0.6029 (4) | 0.1569 (14) | 0.4847 (6) | 0.064 (3)* | 0.52 |
H7A | 0.5761 | 0.0335 | 0.5139 | 0.077* | 0.52 |
C8A | 0.6038 (4) | 0.1604 (13) | 0.3731 (6) | 0.054 (3)* | 0.52 |
H8A | 0.5777 | 0.0394 | 0.3277 | 0.064* | 0.52 |
C3B | 0.6455 (9) | 0.350 (4) | 0.3302 (10) | 0.0396 (10)* | 0.22 |
C4B | 0.7146 (7) | 0.378 (5) | 0.4023 (14) | 0.093 (8)* | 0.22 |
H4B | 0.7601 | 0.3858 | 0.3756 | 0.112* | 0.22 |
C5B | 0.7158 (9) | 0.396 (6) | 0.5141 (13) | 0.119 (12)* | 0.22 |
H5B | 0.7621 | 0.4153 | 0.5623 | 0.143* | 0.22 |
C6B | 0.6479 (11) | 0.385 (6) | 0.5540 (10) | 0.080 (12)* | 0.22 |
H6B | 0.6487 | 0.3971 | 0.6288 | 0.096* | 0.22 |
C7B | 0.5787 (9) | 0.357 (5) | 0.4819 (13) | 0.085 (7)* | 0.22 |
H7B | 0.5333 | 0.3492 | 0.5086 | 0.102* | 0.22 |
C8B | 0.5775 (7) | 0.339 (4) | 0.3701 (12) | 0.083 (7)* | 0.22 |
H8B | 0.5313 | 0.3197 | 0.3219 | 0.100* | 0.22 |
C3C | 0.6308 (9) | 0.350 (3) | 0.3168 (8) | 0.0396 (10)* | 0.26 |
C4C | 0.6507 (8) | 0.551 (3) | 0.3865 (10) | 0.074 (5)* | 0.26 |
H4C | 0.6707 | 0.6933 | 0.3607 | 0.089* | 0.26 |
C5C | 0.6407 (8) | 0.538 (3) | 0.4946 (10) | 0.084 (6)* | 0.26 |
H5C | 0.6540 | 0.6718 | 0.5412 | 0.100* | 0.26 |
C6C | 0.6108 (9) | 0.324 (3) | 0.5331 (9) | 0.056 (4)* | 0.26 |
H6C | 0.6041 | 0.3155 | 0.6054 | 0.067* | 0.26 |
C7C | 0.5908 (10) | 0.124 (3) | 0.4634 (12) | 0.084 (8)* | 0.26 |
H7C | 0.5708 | −0.0191 | 0.4891 | 0.101* | 0.26 |
C8C | 0.6008 (10) | 0.137 (3) | 0.3553 (11) | 0.069 (7)* | 0.26 |
H8C | 0.5875 | 0.0024 | 0.3086 | 0.083* | 0.26 |
O4 | 0.33578 (14) | 0.4495 (5) | 0.0742 (2) | 0.0455 (7) | |
O5 | 0.46148 (14) | 0.4403 (5) | 0.1211 (3) | 0.0507 (7) | |
N | 0.32475 (14) | 0.9385 (5) | 0.0681 (2) | 0.0341 (6) | |
H3A | 0.3271 | 1.1031 | 0.0727 | 0.051* | |
H3B | 0.2882 | 0.8832 | 0.1022 | 0.051* | |
H3C | 0.3142 | 0.8935 | −0.0020 | 0.051* | |
C9 | 0.39752 (18) | 0.5525 (6) | 0.1028 (3) | 0.0327 (7) | |
C10 | 0.39911 (17) | 0.8317 (6) | 0.1203 (3) | 0.0317 (7) | |
H10 | 0.4398 | 0.9042 | 0.0870 | 0.038* | |
C11 | 0.4137 (2) | 0.8915 (9) | 0.2413 (3) | 0.0542 (10) | |
H11A | 0.4260 | 1.0641 | 0.2517 | 0.081* | |
H11B | 0.4556 | 0.7932 | 0.2783 | 0.081* | |
H11C | 0.3687 | 0.8550 | 0.2708 | 0.081* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0432 (13) | 0.0249 (12) | 0.0753 (16) | 0.0072 (11) | 0.0258 (11) | 0.0048 (13) |
O2 | 0.0320 (11) | 0.0319 (12) | 0.0777 (16) | 0.0038 (11) | 0.0122 (10) | 0.0099 (14) |
O3 | 0.0356 (12) | 0.0256 (12) | 0.0698 (15) | −0.0005 (11) | 0.0195 (10) | 0.0030 (12) |
C1 | 0.0334 (16) | 0.0247 (15) | 0.0413 (16) | 0.0000 (13) | 0.0135 (12) | −0.0025 (13) |
C2 | 0.0313 (15) | 0.0231 (14) | 0.0483 (17) | −0.0013 (13) | 0.0121 (12) | 0.0002 (14) |
O4 | 0.0329 (12) | 0.0208 (11) | 0.0810 (18) | −0.0039 (10) | 0.0061 (11) | −0.0020 (12) |
O5 | 0.0341 (12) | 0.0279 (12) | 0.0899 (19) | 0.0075 (11) | 0.0110 (11) | 0.0061 (13) |
N | 0.0307 (13) | 0.0221 (12) | 0.0499 (15) | 0.0014 (12) | 0.0083 (11) | −0.0003 (12) |
C9 | 0.0292 (15) | 0.0227 (15) | 0.0471 (17) | 0.0012 (12) | 0.0096 (13) | 0.0006 (13) |
C10 | 0.0259 (14) | 0.0221 (14) | 0.0477 (17) | −0.0010 (12) | 0.0088 (12) | −0.0035 (14) |
C11 | 0.057 (2) | 0.049 (2) | 0.053 (2) | 0.0018 (19) | 0.0009 (17) | −0.0112 (19) |
Geometric parameters (Å, º) top
O1—C2 | 1.422 (4) | C6B—H6B | 0.9300 |
O1—H1A | 0.8200 | C7B—C8B | 1.3900 |
O2—C1 | 1.270 (4) | C7B—H7B | 0.9300 |
O2—H2A | 0.8200 | C8B—H8B | 0.9300 |
O3—C1 | 1.230 (4) | C3C—C4C | 1.3900 |
C1—C2 | 1.519 (5) | C3C—C8C | 1.3900 |
C2—C3C | 1.451 (10) | C4C—C5C | 1.3900 |
C2—C3A | 1.543 (6) | C4C—H4C | 0.9300 |
C2—C3B | 1.546 (13) | C5C—C6C | 1.3900 |
C2—H2 | 0.9800 | C5C—H5C | 0.9300 |
C3A—C4A | 1.3900 | C6C—C7C | 1.3900 |
C3A—C8A | 1.3900 | C6C—H6C | 0.9300 |
C4A—C5A | 1.3900 | C7C—C8C | 1.3900 |
C4A—H4A | 0.9300 | C7C—H7C | 0.9300 |
C5A—C6A | 1.3900 | C8C—H8C | 0.9300 |
C5A—H5A | 0.9300 | O4—C9 | 1.224 (4) |
C6A—C7A | 1.3900 | O5—C9 | 1.272 (4) |
C6A—H6A | 0.9300 | N—C10 | 1.479 (4) |
C7A—C8A | 1.3900 | N—H3A | 0.8900 |
C7A—H7A | 0.9300 | N—H3B | 0.8900 |
C8A—H8A | 0.9300 | N—H3C | 0.8900 |
C3B—C4B | 1.3900 | C9—C10 | 1.521 (4) |
C3B—C8B | 1.3900 | C10—C11 | 1.514 (5) |
C4B—C5B | 1.3900 | C10—H10 | 0.9800 |
C4B—H4B | 0.9300 | C11—H11A | 0.9600 |
C5B—C6B | 1.3900 | C11—H11B | 0.9600 |
C5B—H5B | 0.9300 | C11—H11C | 0.9600 |
C6B—C7B | 1.3900 | | |
| | | |
C2—O1—H1A | 109.5 | C5B—C6B—H6B | 120.0 |
C1—O2—H2A | 109.5 | C7B—C6B—H6B | 120.0 |
O3—C1—O2 | 122.0 (3) | C6B—C7B—C8B | 120.0 |
O3—C1—C2 | 120.5 (3) | C6B—C7B—H7B | 120.0 |
O2—C1—C2 | 117.4 (3) | C8B—C7B—H7B | 120.0 |
O1—C2—C3C | 117.9 (7) | C7B—C8B—C3B | 120.0 |
O1—C2—C1 | 108.6 (3) | C7B—C8B—H8B | 120.0 |
C3C—C2—C1 | 107.8 (7) | C3B—C8B—H8B | 120.0 |
O1—C2—C3A | 109.1 (4) | C4C—C3C—C8C | 120.0 |
C3C—C2—C3A | 9.2 (8) | C4C—C3C—C2 | 122.5 (10) |
C1—C2—C3A | 109.7 (4) | C8C—C3C—C2 | 117.3 (10) |
O1—C2—C3B | 108.6 (7) | C5C—C4C—C3C | 120.0 |
C3C—C2—C3B | 10.2 (9) | C5C—C4C—H4C | 120.0 |
C1—C2—C3B | 108.8 (8) | C3C—C4C—H4C | 120.0 |
C3A—C2—C3B | 1.5 (8) | C6C—C5C—C4C | 120.0 |
O1—C2—H2 | 109.8 | C6C—C5C—H5C | 120.0 |
C3C—C2—H2 | 102.8 | C4C—C5C—H5C | 120.0 |
C1—C2—H2 | 109.8 | C5C—C6C—C7C | 120.0 |
C3A—C2—H2 | 109.8 | C5C—C6C—H6C | 120.0 |
C3B—C2—H2 | 111.3 | C7C—C6C—H6C | 120.0 |
C4A—C3A—C8A | 120.0 | C6C—C7C—C8C | 120.0 |
C4A—C3A—C2 | 120.3 (4) | C6C—C7C—H7C | 120.0 |
C8A—C3A—C2 | 119.7 (4) | C8C—C7C—H7C | 120.0 |
C3A—C4A—C5A | 120.0 | C7C—C8C—C3C | 120.0 |
C3A—C4A—H4A | 120.0 | C7C—C8C—H8C | 120.0 |
C5A—C4A—H4A | 120.0 | C3C—C8C—H8C | 120.0 |
C6A—C5A—C4A | 120.0 | C10—N—H3A | 109.5 |
C6A—C5A—H5A | 120.0 | C10—N—H3B | 109.5 |
C4A—C5A—H5A | 120.0 | H3A—N—H3B | 109.5 |
C5A—C6A—C7A | 120.0 | C10—N—H3C | 109.5 |
C5A—C6A—H6A | 120.0 | H3A—N—H3C | 109.5 |
C7A—C6A—H6A | 120.0 | H3B—N—H3C | 109.5 |
C6A—C7A—C8A | 120.0 | O4—C9—O5 | 124.2 (3) |
C6A—C7A—H7A | 120.0 | O4—C9—C10 | 118.9 (3) |
C8A—C7A—H7A | 120.0 | O5—C9—C10 | 116.9 (3) |
C7A—C8A—C3A | 120.0 | N—C10—C11 | 109.2 (3) |
C7A—C8A—H8A | 120.0 | N—C10—C9 | 109.4 (3) |
C3A—C8A—H8A | 120.0 | C11—C10—C9 | 110.4 (3) |
C4B—C3B—C8B | 120.0 | N—C10—H10 | 109.3 |
C4B—C3B—C2 | 118.5 (10) | C11—C10—H10 | 109.3 |
C8B—C3B—C2 | 121.4 (10) | C9—C10—H10 | 109.3 |
C3B—C4B—C5B | 120.0 | C10—C11—H11A | 109.5 |
C3B—C4B—H4B | 120.0 | C10—C11—H11B | 109.5 |
C5B—C4B—H4B | 120.0 | H11A—C11—H11B | 109.5 |
C6B—C5B—C4B | 120.0 | C10—C11—H11C | 109.5 |
C6B—C5B—H5B | 120.0 | H11A—C11—H11C | 109.5 |
C4B—C5B—H5B | 120.0 | H11B—C11—H11C | 109.5 |
C5B—C6B—C7B | 120.0 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O3i | 0.82 | 1.98 | 2.797 (4) | 171 |
O2—H2A···O5 | 0.82 | 1.67 | 2.461 (4) | 163 |
N—H3A···O4ii | 0.89 | 1.87 | 2.763 (4) | 176 |
N—H3B···O1iii | 0.89 | 1.99 | 2.877 (4) | 173 |
N—H3C···O3iv | 0.89 | 2.12 | 3.000 (4) | 169 |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) x−1/2, y+1/2, z; (iv) −x+1, y, −z. |