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In the title compound, C15H13NO3, an intra­molecular N—H...O bond helps to establish the mol­ecular conformation. In the crystal structure, adjacent mol­ecules inter­act by way of weak C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015516/bv2052sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015516/bv2052Isup2.hkl
Contains datablock I

CCDC reference: 646764

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.055
  • wR factor = 0.166
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.06 PLAT230_ALERT_2_C Hirshfeld Test Diff for O3 - C8 .. 5.95 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C10 .. 5.43 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C10 -C15 1.37 Ang. PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... \P
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.064 Tmax scaled 0.989 Tmin scaled 0.906 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Benzyl (2-formylphenyl)carbamate top
Crystal data top
C15H13NO3F(000) = 536
Mr = 255.26Dx = 1.319 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2405 reflections
a = 12.5862 (8) Åθ = 2.5–25.0°
b = 6.7950 (4) ŵ = 0.09 mm1
c = 15.8427 (10) ÅT = 293 K
β = 108.386 (1)°Block, colourless
V = 1285.75 (14) Å30.45 × 0.27 × 0.12 mm
Z = 4
Data collection top
Bruker SMART1000 CCD
diffractometer
2260 independent reflections
Radiation source: fine-focus sealed tube1533 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 1413
Tmin = 0.851, Tmax = 0.929k = 86
7557 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: difmap (N-H) and geom (C-H)
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.166 w = 1/[σ2(Fo2) + (0.0818P)2 + 0.3927P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2260 reflectionsΔρmax = 0.31 e Å3
172 parametersΔρmin = 0.23 e Å3
4 restraints
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
O10.01011 (15)0.1566 (3)0.18715 (13)0.0789 (6)
O20.36172 (18)0.1766 (3)0.44305 (13)0.0836 (6)
O30.18327 (17)0.1741 (3)0.44657 (11)0.0718 (6)
N10.21209 (16)0.1554 (3)0.31692 (12)0.0546 (5)
H10.14030.14550.30030.065*
C10.0650 (2)0.1602 (4)0.13663 (18)0.0659 (7)
H1A0.02520.16520.07620.079*
C20.18667 (19)0.1576 (3)0.16030 (15)0.0506 (6)
C30.2312 (2)0.1585 (4)0.09015 (17)0.0620 (7)
H30.18310.15970.03200.074*
C40.3443 (3)0.1578 (4)0.1052 (2)0.0739 (8)
H40.37340.15950.05810.089*
C50.4140 (2)0.1544 (4)0.1917 (2)0.0747 (8)
H50.49100.15260.20260.090*
C60.3732 (2)0.1536 (4)0.26283 (19)0.0630 (7)
H60.42260.15190.32060.076*
C70.25942 (19)0.1555 (3)0.24846 (15)0.0482 (5)
C80.2629 (2)0.1686 (4)0.40644 (17)0.0596 (6)
C90.2193 (3)0.2026 (5)0.54259 (18)0.0827 (9)
H9A0.17060.29730.55780.099*
H9B0.29490.25470.56230.099*
C100.2159 (2)0.0120 (4)0.58884 (15)0.0581 (6)
C110.3055 (2)0.1112 (4)0.61580 (17)0.0653 (7)
H110.37200.07470.60630.078*
C120.3009 (3)0.2840 (5)0.65575 (19)0.0774 (8)
H120.36330.36570.67230.093*
C130.2065 (3)0.3400 (5)0.67204 (19)0.0818 (9)
H130.20460.45970.70000.098*
C140.1145 (3)0.2236 (6)0.6482 (2)0.0882 (9)
H140.04980.26220.66020.106*
C150.1176 (2)0.0447 (5)0.60519 (19)0.0757 (7)
H150.05470.03570.58770.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0590 (11)0.1049 (16)0.0685 (13)0.0049 (10)0.0138 (10)0.0041 (11)
O20.0808 (13)0.0918 (15)0.0593 (12)0.0019 (11)0.0048 (10)0.0026 (10)
O30.0920 (13)0.0744 (13)0.0472 (10)0.0028 (10)0.0197 (10)0.0036 (8)
N10.0568 (11)0.0544 (12)0.0443 (11)0.0001 (9)0.0042 (9)0.0027 (9)
C10.0629 (15)0.0735 (18)0.0506 (15)0.0033 (13)0.0025 (12)0.0027 (13)
C20.0578 (13)0.0406 (12)0.0493 (13)0.0011 (10)0.0110 (11)0.0037 (10)
C30.0815 (18)0.0527 (15)0.0510 (14)0.0036 (13)0.0199 (13)0.0012 (11)
C40.089 (2)0.0632 (17)0.083 (2)0.0046 (15)0.0472 (18)0.0051 (15)
C50.0592 (16)0.0676 (19)0.097 (2)0.0022 (13)0.0249 (16)0.0095 (16)
C60.0578 (15)0.0574 (16)0.0659 (17)0.0014 (12)0.0084 (12)0.0050 (12)
C70.0544 (13)0.0332 (11)0.0515 (13)0.0012 (9)0.0088 (10)0.0022 (9)
C80.0712 (16)0.0438 (14)0.0502 (14)0.0012 (12)0.0006 (13)0.0006 (11)
C90.123 (2)0.0719 (19)0.0488 (16)0.0022 (18)0.0209 (16)0.0058 (13)
C100.0749 (14)0.0615 (15)0.0340 (12)0.0018 (12)0.0117 (11)0.0052 (10)
C110.0573 (15)0.082 (2)0.0533 (15)0.0016 (13)0.0127 (12)0.0081 (14)
C120.085 (2)0.080 (2)0.0570 (17)0.0165 (17)0.0080 (15)0.0014 (15)
C130.113 (3)0.078 (2)0.0542 (17)0.0018 (19)0.0257 (17)0.0079 (14)
C140.083 (2)0.117 (2)0.077 (2)0.019 (2)0.0438 (18)0.0030 (17)
C150.0635 (14)0.101 (2)0.0611 (17)0.0193 (15)0.0169 (13)0.0038 (14)
Geometric parameters (Å, º) top
O1—C11.211 (3)C6—C71.378 (3)
O2—C81.197 (3)C6—H60.9300
O3—C81.346 (3)C9—C101.495 (4)
O3—C91.457 (3)C9—H9A0.9700
N1—C81.362 (3)C9—H9B0.9700
N1—C71.392 (3)C10—C111.361 (4)
N1—H10.8600C10—C151.396 (4)
C1—C21.457 (3)C11—C121.344 (4)
C1—H1A0.9300C11—H110.9300
C2—C31.394 (3)C12—C131.347 (4)
C2—C71.408 (3)C12—H120.9300
C3—C41.367 (4)C13—C141.354 (5)
C3—H30.9300C13—H130.9300
C4—C51.375 (4)C14—C151.400 (5)
C4—H40.9300C14—H140.9300
C5—C61.377 (4)C15—H150.9300
C5—H50.9300
C8—O3—C9117.7 (2)O2—C8—N1125.6 (3)
C8—N1—C7129.4 (2)O3—C8—N1108.6 (2)
C8—N1—H1115.3O3—C9—C10110.4 (2)
C7—N1—H1115.3O3—C9—H9A109.6
O1—C1—C2127.0 (2)C10—C9—H9A109.6
O1—C1—H1A116.5O3—C9—H9B109.6
C2—C1—H1A116.5C10—C9—H9B109.6
C3—C2—C7119.5 (2)H9A—C9—H9B108.1
C3—C2—C1116.7 (2)C11—C10—C15117.9 (3)
C7—C2—C1123.9 (2)C11—C10—C9122.6 (3)
C4—C3—C2121.3 (3)C15—C10—C9119.6 (3)
C4—C3—H3119.4C12—C11—C10122.0 (3)
C2—C3—H3119.4C12—C11—H11119.0
C3—C4—C5118.4 (3)C10—C11—H11119.0
C3—C4—H4120.8C11—C12—C13120.6 (3)
C5—C4—H4120.8C11—C12—H12119.7
C4—C5—C6122.0 (3)C13—C12—H12119.7
C4—C5—H5119.0C12—C13—C14120.7 (3)
C6—C5—H5119.0C12—C13—H13119.7
C5—C6—C7120.1 (3)C14—C13—H13119.7
C5—C6—H6120.0C13—C14—C15119.3 (3)
C7—C6—H6120.0C13—C14—H14120.3
C6—C7—N1123.3 (2)C15—C14—H14120.3
C6—C7—C2118.7 (2)C10—C15—C14119.5 (3)
N1—C7—C2117.9 (2)C10—C15—H15120.2
O2—C8—O3125.8 (2)C14—C15—H15120.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.862.012.719 (3)139
C6—H6···O20.932.312.909 (4)122
C13—H13···πi0.932.913.696 (3)143
Symmetry code: (i) x+1/2, y1/2, z+3/2.
 

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