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In the title compound, C9H11N3O2, all bond lengths and angles are normal. The conformation of the molecule is determined by intra- and intermolecular hydrogen bonds.
Supporting information
CCDC reference: 238767
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.085
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C
GOODF01_ALERT_2_C The least squares goodness of fit parameter lies
outside the range 0.80 <> 2.00
Goodness of fit given = 0.799
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C6
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C9 H11 N3 O2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
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, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).
anti-1-(Benzylamino)glyoxime
top
Crystal data top
C9H11N3O2 | Dx = 1.297 Mg m−3 |
Mr = 193.21 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 7310 reflections |
a = 11.6618 (9) Å | θ = 1.8–25.4° |
b = 8.8584 (7) Å | µ = 0.10 mm−1 |
c = 19.163 (2) Å | T = 293 K |
V = 1979.6 (3) Å3 | Prism., yellow |
Z = 8 | 0.50 × 0.28 × 0.11 mm |
F(000) = 816 | |
Data collection top
STOE IPDS-II diffractometer | 1037 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.074 |
Graphite monochromator | θmax = 26.0°, θmin = 2.1° |
Detector resolution: 6.67 pixels mm-1 | h = −13→14 |
ω scan | k = −10→10 |
18058 measured reflections | l = −23→23 |
1935 independent 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)] = 0.034 | See text |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0489P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.80 | (Δ/σ)max < 0.001 |
1935 reflections | Δρmax = 0.14 e Å−3 |
128 parameters | Δρmin = −0.11 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: 0.0139 (14) |
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 | |
O2 | 0.14330 (9) | 0.00228 (13) | −0.51572 (7) | 0.0697 (4) | |
H2 | 0.1043 | −0.0725 | −0.5242 | 0.105* | |
N3 | 0.47068 (10) | 0.24966 (14) | −0.54691 (7) | 0.0514 (4) | |
C8 | 0.42702 (13) | 0.12017 (18) | −0.56430 (8) | 0.0460 (4) | |
O1 | 0.58211 (9) | 0.26497 (13) | −0.57423 (7) | 0.0685 (4) | |
H1 | 0.6085 | 0.3472 | −0.5629 | 0.103* | |
N2 | 0.24940 (11) | −0.01170 (14) | −0.54828 (7) | 0.0512 (4) | |
N1 | 0.48424 (11) | 0.01693 (15) | −0.60172 (7) | 0.0573 (4) | |
H1A | 0.5550 | 0.0369 | −0.6102 | 0.069* | |
C6 | 0.53391 (14) | −0.19577 (18) | −0.67379 (8) | 0.0503 (4) | |
C9 | 0.31152 (14) | 0.10144 (19) | −0.53772 (9) | 0.0564 (5) | |
H9 | 0.2813 | 0.1792 | −0.5108 | 0.068* | |
C7 | 0.44121 (14) | −0.12495 (18) | −0.62975 (10) | 0.0619 (5) | |
H7A | 0.3735 | −0.1067 | −0.6579 | 0.074* | |
H7B | 0.4204 | −0.1923 | −0.5919 | 0.074* | |
C5 | 0.55686 (16) | −0.1436 (2) | −0.74013 (10) | 0.0669 (5) | |
H5 | 0.5127 | −0.0660 | −0.7587 | 0.080* | |
C1 | 0.59996 (17) | −0.3114 (2) | −0.64838 (10) | 0.0703 (5) | |
H1B | 0.5858 | −0.3489 | −0.6039 | 0.084* | |
C3 | 0.70875 (19) | −0.3178 (3) | −0.75312 (14) | 0.0837 (7) | |
H3 | 0.7681 | −0.3580 | −0.7797 | 0.100* | |
C4 | 0.64410 (19) | −0.2048 (3) | −0.77915 (11) | 0.0769 (6) | |
H4 | 0.6586 | −0.1681 | −0.8237 | 0.092* | |
C2 | 0.68741 (18) | −0.3730 (3) | −0.68810 (13) | 0.0873 (7) | |
H2A | 0.7314 | −0.4518 | −0.6704 | 0.105* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0516 (7) | 0.0558 (7) | 0.1019 (10) | −0.0096 (6) | 0.0264 (6) | −0.0264 (7) |
N3 | 0.0402 (7) | 0.0501 (8) | 0.0640 (9) | −0.0032 (6) | 0.0020 (7) | −0.0112 (7) |
C8 | 0.0441 (9) | 0.0436 (9) | 0.0504 (9) | 0.0023 (8) | −0.0034 (7) | −0.0055 (7) |
O1 | 0.0457 (7) | 0.0647 (8) | 0.0952 (9) | −0.0119 (6) | 0.0088 (6) | −0.0231 (7) |
N2 | 0.0438 (7) | 0.0482 (8) | 0.0614 (8) | −0.0004 (7) | 0.0066 (6) | −0.0069 (7) |
N1 | 0.0446 (8) | 0.0517 (8) | 0.0756 (10) | −0.0027 (7) | 0.0056 (7) | −0.0224 (7) |
C6 | 0.0500 (10) | 0.0482 (9) | 0.0528 (10) | −0.0033 (8) | 0.0012 (8) | −0.0128 (8) |
C9 | 0.0539 (10) | 0.0445 (9) | 0.0707 (12) | −0.0014 (9) | 0.0105 (9) | −0.0152 (9) |
C7 | 0.0569 (11) | 0.0515 (10) | 0.0772 (12) | −0.0030 (9) | 0.0072 (9) | −0.0203 (9) |
C5 | 0.0728 (13) | 0.0650 (12) | 0.0630 (12) | 0.0011 (10) | −0.0022 (10) | 0.0004 (9) |
C1 | 0.0807 (14) | 0.0699 (12) | 0.0604 (11) | 0.0133 (11) | 0.0041 (10) | −0.0016 (10) |
C3 | 0.0726 (15) | 0.0826 (15) | 0.0958 (18) | −0.0039 (13) | 0.0240 (12) | −0.0328 (14) |
C4 | 0.0899 (15) | 0.0836 (15) | 0.0573 (12) | −0.0155 (13) | 0.0173 (11) | −0.0119 (11) |
C2 | 0.0770 (15) | 0.0814 (15) | 0.1034 (18) | 0.0280 (12) | 0.0000 (13) | −0.0105 (13) |
Geometric parameters (Å, º) top
O2—N2 | 1.3912 (16) | C9—H9 | 0.9300 |
O2—H2 | 0.8200 | C7—H7A | 0.9700 |
N3—C8 | 1.2986 (18) | C7—H7B | 0.9700 |
N3—O1 | 1.4075 (16) | C5—C4 | 1.374 (3) |
C8—N1 | 1.3400 (19) | C5—H5 | 0.9300 |
C8—C9 | 1.449 (2) | C1—C2 | 1.385 (3) |
O1—H1 | 0.8200 | C1—H1B | 0.9300 |
N2—C9 | 1.2532 (19) | C3—C4 | 1.349 (3) |
N1—C7 | 1.456 (2) | C3—C2 | 1.362 (3) |
N1—H1A | 0.8600 | C3—H3 | 0.9300 |
C6—C1 | 1.371 (2) | C4—H4 | 0.9300 |
C6—C5 | 1.379 (2) | C2—H2A | 0.9300 |
C6—C7 | 1.508 (2) | | |
| | | |
N2—O2—H2 | 109.5 | N1—C7—H7B | 110.0 |
C8—N3—O1 | 110.59 (12) | C6—C7—H7B | 110.0 |
N3—C8—N1 | 123.02 (14) | H7A—C7—H7B | 108.4 |
N3—C8—C9 | 112.04 (14) | C4—C5—C6 | 120.88 (19) |
N1—C8—C9 | 124.94 (15) | C4—C5—H5 | 119.6 |
N3—O1—H1 | 109.5 | C6—C5—H5 | 119.6 |
C9—N2—O2 | 111.75 (13) | C6—C1—C2 | 120.87 (19) |
C8—N1—C7 | 127.94 (13) | C6—C1—H1B | 119.6 |
C8—N1—H1A | 116.0 | C2—C1—H1B | 119.6 |
C7—N1—H1A | 116.0 | C4—C3—C2 | 120.2 (2) |
C1—C6—C5 | 117.96 (16) | C4—C3—H3 | 119.9 |
C1—C6—C7 | 120.98 (16) | C2—C3—H3 | 119.9 |
C5—C6—C7 | 121.04 (16) | C3—C4—C5 | 120.4 (2) |
N2—C9—C8 | 124.89 (15) | C3—C4—H4 | 119.8 |
N2—C9—H9 | 117.6 | C5—C4—H4 | 119.8 |
C8—C9—H9 | 117.6 | C3—C2—C1 | 119.7 (2) |
N1—C7—C6 | 108.57 (13) | C3—C2—H2A | 120.1 |
N1—C7—H7A | 110.0 | C1—C2—H2A | 120.1 |
C6—C7—H7A | 110.0 | | |
| | | |
O1—N3—C8—N1 | 1.5 (2) | C5—C6—C7—N1 | −77.2 (2) |
O1—N3—C8—C9 | −179.26 (13) | C1—C6—C5—C4 | −0.7 (3) |
N3—C8—N1—C7 | −173.74 (16) | C7—C6—C5—C4 | 177.63 (16) |
C9—C8—N1—C7 | 7.2 (3) | C5—C6—C1—C2 | 0.4 (3) |
O2—N2—C9—C8 | 179.56 (15) | C7—C6—C1—C2 | −177.93 (17) |
N3—C8—C9—N2 | 178.43 (15) | C2—C3—C4—C5 | 0.6 (3) |
N1—C8—C9—N2 | −2.4 (3) | C6—C5—C4—C3 | 0.2 (3) |
C8—N1—C7—C6 | 174.75 (15) | C4—C3—C2—C1 | −0.8 (3) |
C1—C6—C7—N1 | 101.08 (18) | C6—C1—C2—C3 | 0.4 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 2.05 | 2.7805 (16) | 148 |
O2—H2···N3ii | 0.82 | 1.85 | 2.6705 (17) | 174 |
N1—H1A···O1 | 0.86 | 2.16 | 2.5314 (17) | 106 |
Symmetry codes: (i) x+1/2, −y+1/2, −z−1; (ii) −x+1/2, y−1/2, z. |
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