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The structure of the title compound, C9H11NO2, (I), comprises a flat mol­ecule arranged, head-to-tail, in linear ribbon arrays via a N—H...O=C association. These ribbons end-on form a herring-bone structure interconnected via N—H...N association. The structure was first determined in 1987 [Sinha & Pattabhi (1987). Proc. Indian Acad. Sci. Chem. Sci. 98, 229–234] in the orthorhombic space group P212121, with R = 0.120, whereas similar cell dimensions and an increased β angle in the present study resulted in monoclinic space group P21/c, with R = 0.065.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802009674/cv6118sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802009674/cv6118Isup2.hkl
Contains datablock I

CCDC reference: 189882

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.065
  • wR factor = 0.181
  • Data-to-parameter ratio = 12.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 24.99 From the CIF: _reflns_number_total 1352 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1542 Completeness (_total/calc) 87.68% Alert B: < 90% complete (theta max?)
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

Ethyl 4-aminobenzoate top
Crystal data top
C9H11NO2F(000) = 352
Mr = 165.19Dx = 1.259 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.198 (2) ÅCell parameters from 3445 reflections
b = 5.430 (1) Åθ = 1.0–27.5°
c = 19.592 (5) ŵ = 0.09 mm1
β = 91.350 (6)°T = 120 K
V = 871.8 (4) Å3Block, colourless
Z = 40.10 × 0.08 × 0.03 mm
Data collection top
Bruker–Nonius KappaCCD area-detector
diffractometer
1352 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode686 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.097
Detector resolution: 9.091 pixels mm-1θmax = 25.0°, θmin = 2.1°
φ and ω scansh = 99
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 65
Tmin = 0.991, Tmax = 0.997l = 2123
3445 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0712P)2]
where P = (Fo2 + 2Fc2)/3
1352 reflections(Δ/σ)max < 0.001
110 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.24 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.7720 (3)0.4029 (5)0.3662 (1)0.0403 (9)
O20.6328 (3)0.6836 (5)0.4257 (1)0.0364 (8)
N10.0252 (4)0.1297 (6)0.2947 (2)0.0384 (10)
H110.06440.20870.30540.048*
H120.01900.00530.26990.048*
C10.4808 (4)0.3984 (7)0.3602 (2)0.0284 (10)
C20.4679 (5)0.1868 (7)0.3205 (2)0.0323 (11)
H20.56430.10240.30810.040*
C30.3180 (4)0.0967 (7)0.2987 (2)0.0321 (11)
H30.31240.04760.27140.040*
C40.1747 (5)0.2170 (7)0.3168 (2)0.0287 (10)
C50.1861 (5)0.4297 (8)0.3560 (2)0.0340 (11)
H50.08960.51420.36820.042*
C60.3370 (4)0.5200 (7)0.3775 (2)0.0322 (11)
H60.34280.66580.40420.040*
C70.6417 (5)0.4910 (7)0.3831 (2)0.0331 (11)
C80.7868 (5)0.7847 (8)0.4499 (2)0.0404 (12)
H710.84850.85260.41130.050*
H720.85380.65570.47270.050*
C90.7458 (5)0.9862 (7)0.4998 (2)0.0401 (12)
H730.67181.10480.47750.050*
H740.84621.07020.51480.050*
H750.69280.91410.53940.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0234 (19)0.047 (2)0.050 (2)0.0006 (15)0.0047 (14)0.0056 (15)
O20.0260 (17)0.0366 (18)0.0464 (19)0.0046 (13)0.0018 (13)0.0087 (15)
N10.023 (2)0.041 (2)0.050 (2)0.0043 (16)0.0014 (16)0.0106 (18)
C10.022 (2)0.027 (3)0.036 (3)0.0003 (18)0.0008 (18)0.0029 (19)
C20.026 (3)0.038 (3)0.032 (3)0.006 (2)0.0066 (18)0.002 (2)
C30.025 (3)0.030 (3)0.041 (3)0.0025 (19)0.001 (2)0.0021 (19)
C40.022 (2)0.028 (3)0.036 (3)0.0027 (19)0.0016 (18)0.002 (2)
C50.025 (3)0.031 (3)0.045 (3)0.0020 (19)0.002 (2)0.001 (2)
C60.026 (3)0.028 (3)0.043 (3)0.0013 (19)0.0011 (19)0.0017 (19)
C70.028 (3)0.033 (3)0.038 (3)0.003 (2)0.001 (2)0.001 (2)
C80.023 (3)0.053 (3)0.045 (3)0.010 (2)0.001 (2)0.001 (2)
C90.029 (3)0.045 (3)0.047 (3)0.004 (2)0.005 (2)0.005 (2)
Geometric parameters (Å, º) top
O1—C71.223 (4)C3—H30.95
O2—C71.341 (5)C4—C51.389 (5)
O2—C81.446 (4)C5—C61.387 (5)
N1—C41.374 (4)C5—H50.95
N1—H110.88C6—H60.95
N1—H120.88C8—C91.511 (5)
C1—C21.389 (5)C8—H710.99
C1—C61.400 (5)C8—H720.99
C1—C71.472 (5)C9—H730.98
C2—C31.381 (5)C9—H740.98
C2—H20.95C9—H750.98
C3—C41.397 (5)
C7—O2—C8116.1 (3)C5—C6—C1120.6 (4)
C4—N1—H11120.0C5—C6—H6119.7
C4—N1—H12120.0C1—C6—H6119.7
H11—N1—H12120.0O1—C7—O2122.2 (4)
C2—C1—C6118.2 (3)O1—C7—C1124.5 (4)
C2—C1—C7120.6 (4)O2—C7—C1113.3 (4)
C6—C1—C7121.2 (4)O2—C8—C9106.3 (3)
C3—C2—C1121.4 (4)O2—C8—H71110.5
C3—C2—H2119.3C9—C8—H71110.5
C1—C2—H2119.3O2—C8—H72110.5
C2—C3—C4120.3 (4)C9—C8—H72110.5
C2—C3—H3119.9H71—C8—H72108.7
C4—C3—H3119.9C8—C9—H73109.5
N1—C4—C5120.6 (4)C8—C9—H74109.5
N1—C4—C3120.5 (4)H73—C9—H74109.5
C5—C4—C3118.8 (3)C8—C9—H75109.5
C6—C5—C4120.7 (4)H73—C9—H75109.5
C6—C5—H5119.7H74—C9—H75109.5
C4—C5—H5119.7
C6—C1—C2—C30.3 (5)C7—C1—C6—C5179.5 (4)
C7—C1—C2—C3179.8 (4)C8—O2—C7—O11.1 (5)
C1—C2—C3—C40.5 (6)C8—O2—C7—C1179.6 (3)
C2—C3—C4—N1179.3 (3)C2—C1—C7—O14.8 (6)
C2—C3—C4—C50.9 (5)C6—C1—C7—O1175.2 (4)
N1—C4—C5—C6179.1 (4)C2—C1—C7—O2174.5 (3)
C3—C4—C5—C60.7 (6)C6—C1—C7—O25.5 (5)
C4—C5—C6—C10.0 (6)C7—O2—C8—C9176.6 (3)
C2—C1—C6—C50.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O1i0.882.102.934 (4)158
N1—H12···N1ii0.882.383.252 (3)174
Symmetry codes: (i) x1, y, z; (ii) x, y1/2, z+1/2.
 

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