Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805022221/sj6117sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805022221/sj6117Isup2.hkl |
CCDC reference: 282637
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.030
- wR factor = 0.084
- Data-to-parameter ratio = 9.7
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.847 1.000 Tmin(prime) and Tmax expected: 0.937 0.957 RR(prime) = 0.865 Please check that your absorption correction is appropriate. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.66 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C6 .. 3.01 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.
C6H6NO2+·H2PO4− | F(000) = 456 |
Mr = 221.10 | Dx = 1.667 Mg m−3 Dm = 1.652 Mg m−3 Dm measured by flotation in CHBr3 and CCl4 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.158 (5) Å | Cell parameters from 25 reflections |
b = 10.593 (4) Å | θ = 9.7–14.3° |
c = 7.001 (3) Å | µ = 0.32 mm−1 |
β = 102.35 (3)° | T = 293 K |
V = 880.8 (6) Å3 | Needle, colourless |
Z = 4 | 0.20 × 0.17 × 0.14 mm |
Nonius MACH3 sealed-tube diffractometer | 1317 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.047 |
Graphite monochromator | θmax = 25.0°, θmin = 2.6° |
ω/2θ scans | h = −14→14 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→1 |
Tmin = 0.847, Tmax = 1.000 | l = 0→8 |
1880 measured reflections | 3 standard reflections every 60 min |
1545 independent reflections | intensity decay: none |
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)] = 0.030 | All H-atom parameters refined |
wR(F2) = 0.084 | w = 1/[σ2(Fo2) + (0.0512P)2 + 0.2334P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
1545 reflections | Δρmax = 0.25 e Å−3 |
160 parameters | Δρmin = −0.37 e Å−3 |
0 restraints | Extinction correction: SHELXTL/PC (Bruker, 2000), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.131 (7) |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.72318 (13) | 0.57178 (16) | 0.9647 (2) | 0.0357 (4) | |
H1 | 0.7311 (19) | 0.649 (2) | 0.989 (3) | 0.040 (6)* | |
C2 | 0.62653 (16) | 0.53386 (18) | 0.8483 (3) | 0.0345 (5) | |
H2 | 0.569 (2) | 0.595 (2) | 0.800 (3) | 0.044 (6)* | |
C3 | 0.61118 (15) | 0.40873 (17) | 0.7980 (3) | 0.0290 (4) | |
C4 | 0.69727 (16) | 0.32384 (19) | 0.8715 (3) | 0.0359 (4) | |
H4 | 0.687 (2) | 0.236 (3) | 0.839 (4) | 0.059 (7)* | |
C5 | 0.79443 (18) | 0.3665 (2) | 0.9921 (3) | 0.0424 (5) | |
H5 | 0.854 (2) | 0.315 (2) | 1.044 (3) | 0.051 (6)* | |
C6 | 0.80657 (17) | 0.4919 (2) | 1.0363 (3) | 0.0386 (5) | |
H6 | 0.877 (2) | 0.530 (2) | 1.127 (4) | 0.056 (7)* | |
C31 | 0.50543 (15) | 0.36374 (17) | 0.6669 (3) | 0.0310 (4) | |
O1A | 0.50164 (11) | 0.26655 (13) | 0.5767 (2) | 0.0419 (4) | |
O1B | 0.41945 (12) | 0.44044 (14) | 0.6607 (3) | 0.0446 (4) | |
H1B | 0.366 (3) | 0.405 (3) | 0.593 (5) | 0.069 (9)* | |
P1 | 0.87510 (3) | 0.88988 (4) | 0.05786 (6) | 0.0245 (2) | |
O1 | 0.85483 (12) | 1.03547 (12) | 0.0364 (2) | 0.0349 (4) | |
H1P | 0.916 (2) | 1.074 (3) | 0.055 (4) | 0.058 (8)* | |
O2 | 0.93597 (11) | 0.87378 (13) | 0.2765 (2) | 0.0354 (4) | |
H2P | 0.943 (3) | 0.800 (3) | 0.318 (5) | 0.084 (10)* | |
O3 | 0.95263 (11) | 0.84746 (12) | −0.07246 (19) | 0.0351 (3) | |
O4 | 0.76205 (10) | 0.82621 (12) | 0.0151 (2) | 0.0359 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0371 (9) | 0.0304 (9) | 0.0394 (9) | −0.0104 (7) | 0.0079 (7) | −0.0054 (7) |
C2 | 0.0308 (10) | 0.0295 (10) | 0.0424 (11) | −0.0014 (8) | 0.0062 (8) | −0.0007 (8) |
C3 | 0.0259 (9) | 0.0281 (9) | 0.0333 (9) | −0.0019 (7) | 0.0072 (7) | 0.0007 (7) |
C4 | 0.0324 (9) | 0.0296 (10) | 0.0452 (11) | 0.0002 (8) | 0.0072 (8) | 0.0012 (8) |
C5 | 0.0321 (10) | 0.0417 (11) | 0.0488 (12) | 0.0022 (9) | −0.0015 (9) | 0.0056 (9) |
C6 | 0.0317 (10) | 0.0479 (11) | 0.0336 (10) | −0.0087 (9) | 0.0014 (8) | 0.0034 (9) |
C31 | 0.0265 (9) | 0.0303 (9) | 0.0367 (10) | −0.0028 (7) | 0.0078 (7) | 0.0003 (7) |
O1A | 0.0356 (7) | 0.0362 (8) | 0.0530 (9) | −0.0059 (6) | 0.0077 (6) | −0.0137 (6) |
O1B | 0.0260 (7) | 0.0393 (8) | 0.0636 (10) | 0.0008 (6) | −0.0014 (7) | −0.0112 (7) |
P1 | 0.0201 (3) | 0.0212 (3) | 0.0306 (3) | −0.00124 (16) | 0.00183 (18) | 0.00011 (17) |
O1 | 0.0295 (7) | 0.0239 (7) | 0.0500 (8) | 0.0014 (5) | 0.0054 (6) | 0.0013 (5) |
O2 | 0.0353 (7) | 0.0317 (7) | 0.0355 (8) | −0.0059 (6) | −0.0011 (6) | 0.0030 (6) |
O3 | 0.0335 (7) | 0.0299 (7) | 0.0436 (8) | −0.0046 (5) | 0.0122 (6) | −0.0084 (6) |
O4 | 0.0219 (6) | 0.0306 (7) | 0.0516 (8) | −0.0037 (5) | −0.0004 (5) | 0.0004 (6) |
N1—C6 | 1.334 (3) | C6—H6 | 1.03 (3) |
N1—C2 | 1.340 (3) | C31—O1A | 1.204 (2) |
N1—H1 | 0.83 (3) | C31—O1B | 1.317 (2) |
C2—C3 | 1.374 (3) | O1B—H1B | 0.81 (3) |
C2—H2 | 0.96 (2) | P1—O4 | 1.5026 (13) |
C3—C4 | 1.392 (3) | P1—O3 | 1.5135 (14) |
C3—C31 | 1.489 (3) | P1—O2 | 1.5603 (16) |
C4—C5 | 1.373 (3) | P1—O1 | 1.5640 (14) |
C4—H4 | 0.96 (3) | O1—H1P | 0.83 (3) |
C5—C6 | 1.364 (3) | O2—H2P | 0.84 (4) |
C5—H5 | 0.91 (3) | ||
C6—N1—C2 | 122.37 (18) | N1—C6—C5 | 119.73 (19) |
C6—N1—H1 | 119.8 (16) | N1—C6—H6 | 116.8 (14) |
C2—N1—H1 | 117.8 (16) | C5—C6—H6 | 123.5 (14) |
N1—C2—C3 | 119.89 (18) | O1A—C31—O1B | 124.71 (18) |
N1—C2—H2 | 119.5 (14) | O1A—C31—C3 | 121.89 (17) |
C3—C2—H2 | 120.6 (14) | O1B—C31—C3 | 113.40 (16) |
C2—C3—C4 | 118.57 (18) | C31—O1B—H1B | 106 (2) |
C2—C3—C31 | 121.25 (17) | O4—P1—O3 | 114.08 (8) |
C4—C3—C31 | 120.18 (17) | O4—P1—O2 | 111.58 (8) |
C5—C4—C3 | 119.64 (19) | O3—P1—O2 | 109.45 (8) |
C5—C4—H4 | 120.8 (15) | O4—P1—O1 | 107.75 (8) |
C3—C4—H4 | 119.6 (15) | O3—P1—O1 | 109.92 (8) |
C6—C5—C4 | 119.79 (19) | O2—P1—O1 | 103.52 (8) |
C6—C5—H5 | 116.9 (16) | P1—O1—H1P | 110.2 (19) |
C4—C5—H5 | 123.3 (16) | P1—O2—H2P | 116 (2) |
C6—N1—C2—C3 | −0.4 (3) | C2—N1—C6—C5 | −0.4 (3) |
N1—C2—C3—C4 | 0.5 (3) | C4—C5—C6—N1 | 1.1 (3) |
N1—C2—C3—C31 | −179.18 (17) | C2—C3—C31—O1A | 158.11 (19) |
C2—C3—C4—C5 | 0.3 (3) | C4—C3—C31—O1A | −21.5 (3) |
C31—C3—C4—C5 | 179.91 (18) | C2—C3—C31—O1B | −21.6 (3) |
C3—C4—C5—C6 | −1.1 (3) | C4—C3—C31—O1B | 158.73 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4i | 0.83 (3) | 1.92 (3) | 2.746 (2) | 171 (2) |
O1B—H1B···O4ii | 0.81 (3) | 1.78 (3) | 2.586 (2) | 169 (3) |
O1—H1P···O3iii | 0.83 (3) | 1.78 (3) | 2.613 (2) | 175 (3) |
O2—H2P···O3iv | 0.84 (4) | 1.73 (4) | 2.561 (2) | 173 (3) |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+2, −y+2, −z; (iv) x, −y+3/2, z+1/2. |
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