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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804004799/cv6275sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804004799/cv6275Isup2.hkl
Contains datablock I

CCDC reference: 238767

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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
C9H11N3O2Dx = 1.297 Mg m3
Mr = 193.21Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 7310 reflections
a = 11.6618 (9) Åθ = 1.8–25.4°
b = 8.8584 (7) ŵ = 0.10 mm1
c = 19.163 (2) ÅT = 293 K
V = 1979.6 (3) Å3Prism., yellow
Z = 80.50 × 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 tubeRint = 0.074
Graphite monochromatorθmax = 26.0°, θmin = 2.1°
Detector resolution: 6.67 pixels mm-1h = 1314
ω scank = 1010
18058 measured reflectionsl = 2323
1935 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034See 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 reflectionsΔρmax = 0.14 e Å3
128 parametersΔρmin = 0.11 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
O20.14330 (9)0.00228 (13)0.51572 (7)0.0697 (4)
H20.10430.07250.52420.105*
N30.47068 (10)0.24966 (14)0.54691 (7)0.0514 (4)
C80.42702 (13)0.12017 (18)0.56430 (8)0.0460 (4)
O10.58211 (9)0.26497 (13)0.57423 (7)0.0685 (4)
H10.60850.34720.56290.103*
N20.24940 (11)0.01170 (14)0.54828 (7)0.0512 (4)
N10.48424 (11)0.01693 (15)0.60172 (7)0.0573 (4)
H1A0.55500.03690.61020.069*
C60.53391 (14)0.19577 (18)0.67379 (8)0.0503 (4)
C90.31152 (14)0.10144 (19)0.53772 (9)0.0564 (5)
H90.28130.17920.51080.068*
C70.44121 (14)0.12495 (18)0.62975 (10)0.0619 (5)
H7A0.37350.10670.65790.074*
H7B0.42040.19230.59190.074*
C50.55686 (16)0.1436 (2)0.74013 (10)0.0669 (5)
H50.51270.06600.75870.080*
C10.59996 (17)0.3114 (2)0.64838 (10)0.0703 (5)
H1B0.58580.34890.60390.084*
C30.70875 (19)0.3178 (3)0.75312 (14)0.0837 (7)
H30.76810.35800.77970.100*
C40.64410 (19)0.2048 (3)0.77915 (11)0.0769 (6)
H40.65860.16810.82370.092*
C20.68741 (18)0.3730 (3)0.68810 (13)0.0873 (7)
H2A0.73140.45180.67040.105*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0516 (7)0.0558 (7)0.1019 (10)0.0096 (6)0.0264 (6)0.0264 (7)
N30.0402 (7)0.0501 (8)0.0640 (9)0.0032 (6)0.0020 (7)0.0112 (7)
C80.0441 (9)0.0436 (9)0.0504 (9)0.0023 (8)0.0034 (7)0.0055 (7)
O10.0457 (7)0.0647 (8)0.0952 (9)0.0119 (6)0.0088 (6)0.0231 (7)
N20.0438 (7)0.0482 (8)0.0614 (8)0.0004 (7)0.0066 (6)0.0069 (7)
N10.0446 (8)0.0517 (8)0.0756 (10)0.0027 (7)0.0056 (7)0.0224 (7)
C60.0500 (10)0.0482 (9)0.0528 (10)0.0033 (8)0.0012 (8)0.0128 (8)
C90.0539 (10)0.0445 (9)0.0707 (12)0.0014 (9)0.0105 (9)0.0152 (9)
C70.0569 (11)0.0515 (10)0.0772 (12)0.0030 (9)0.0072 (9)0.0203 (9)
C50.0728 (13)0.0650 (12)0.0630 (12)0.0011 (10)0.0022 (10)0.0004 (9)
C10.0807 (14)0.0699 (12)0.0604 (11)0.0133 (11)0.0041 (10)0.0016 (10)
C30.0726 (15)0.0826 (15)0.0958 (18)0.0039 (13)0.0240 (12)0.0328 (14)
C40.0899 (15)0.0836 (15)0.0573 (12)0.0155 (13)0.0173 (11)0.0119 (11)
C20.0770 (15)0.0814 (15)0.1034 (18)0.0280 (12)0.0000 (13)0.0105 (13)
Geometric parameters (Å, º) top
O2—N21.3912 (16)C9—H90.9300
O2—H20.8200C7—H7A0.9700
N3—C81.2986 (18)C7—H7B0.9700
N3—O11.4075 (16)C5—C41.374 (3)
C8—N11.3400 (19)C5—H50.9300
C8—C91.449 (2)C1—C21.385 (3)
O1—H10.8200C1—H1B0.9300
N2—C91.2532 (19)C3—C41.349 (3)
N1—C71.456 (2)C3—C21.362 (3)
N1—H1A0.8600C3—H30.9300
C6—C11.371 (2)C4—H40.9300
C6—C51.379 (2)C2—H2A0.9300
C6—C71.508 (2)
N2—O2—H2109.5N1—C7—H7B110.0
C8—N3—O1110.59 (12)C6—C7—H7B110.0
N3—C8—N1123.02 (14)H7A—C7—H7B108.4
N3—C8—C9112.04 (14)C4—C5—C6120.88 (19)
N1—C8—C9124.94 (15)C4—C5—H5119.6
N3—O1—H1109.5C6—C5—H5119.6
C9—N2—O2111.75 (13)C6—C1—C2120.87 (19)
C8—N1—C7127.94 (13)C6—C1—H1B119.6
C8—N1—H1A116.0C2—C1—H1B119.6
C7—N1—H1A116.0C4—C3—C2120.2 (2)
C1—C6—C5117.96 (16)C4—C3—H3119.9
C1—C6—C7120.98 (16)C2—C3—H3119.9
C5—C6—C7121.04 (16)C3—C4—C5120.4 (2)
N2—C9—C8124.89 (15)C3—C4—H4119.8
N2—C9—H9117.6C5—C4—H4119.8
C8—C9—H9117.6C3—C2—C1119.7 (2)
N1—C7—C6108.57 (13)C3—C2—H2A120.1
N1—C7—H7A110.0C1—C2—H2A120.1
C6—C7—H7A110.0
O1—N3—C8—N11.5 (2)C5—C6—C7—N177.2 (2)
O1—N3—C8—C9179.26 (13)C1—C6—C5—C40.7 (3)
N3—C8—N1—C7173.74 (16)C7—C6—C5—C4177.63 (16)
C9—C8—N1—C77.2 (3)C5—C6—C1—C20.4 (3)
O2—N2—C9—C8179.56 (15)C7—C6—C1—C2177.93 (17)
N3—C8—C9—N2178.43 (15)C2—C3—C4—C50.6 (3)
N1—C8—C9—N22.4 (3)C6—C5—C4—C30.2 (3)
C8—N1—C7—C6174.75 (15)C4—C3—C2—C10.8 (3)
C1—C6—C7—N1101.08 (18)C6—C1—C2—C30.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.822.052.7805 (16)148
O2—H2···N3ii0.821.852.6705 (17)174
N1—H1A···O10.862.162.5314 (17)106
Symmetry codes: (i) x+1/2, y+1/2, z1; (ii) x+1/2, y1/2, z.
 

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