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The title compound, C14H10ClNO, is a nitro­gen derivative closely related to natural 3',7-epoxy-8,4'-oxy­neolignans, which are of interest because of their cytotoxic activity. Centrosymmetric hydrogen bonding occurs between pairs of mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500543X/sj6049sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680500543X/sj6049IIsup2.hkl
Contains datablock II

CCDC reference: 269866

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.132
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT351_ALERT_3_C Long C-H Bond (0.96A) C8 - H8B ... 1.12 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: SET4 in CAD–4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3–4(Chlorophenyl)-2H-benz[b][1,4]oxazine top
Crystal data top
C14H10ClNOF(000) = 504
Mr = 243.68Dx = 1.435 Mg m3
Monoclinic, P21/cMelting point = 433–434 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 13.861 (3) ÅCell parameters from 25 reflections
b = 5.834 (1) Åθ = 9.8–13.8°
c = 14.903 (3) ŵ = 0.32 mm1
β = 110.65 (3)°T = 298 K
V = 1127.7 (4) Å3Prismatic, light brown
Z = 40.35 × 0.35 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1543 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
Graphite monochromatorθmax = 25.0°, θmin = 2.8°
non–profiled ω/2θ scansh = 160
Absorption correction: psi-scan
(North et al., 1968)
k = 60
Tmin = 0.901, Tmax = 0.970l = 1617
2055 measured reflections2 standard reflections every 120 min
1970 independent reflections intensity decay: <1%
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)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.132 w = 1/[σ2(Fo2) + (0.0668P)2 + 0.5604P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.004
1970 reflectionsΔρmax = 0.47 e Å3
161 parametersΔρmin = 0.27 e Å3
3 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.017 (3)
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
Cl0.03691 (5)1.08109 (15)0.66491 (6)0.0761 (3)
O0.61639 (11)0.6664 (3)0.98852 (11)0.0501 (4)
N0.55017 (14)1.0737 (3)0.88482 (13)0.0414 (4)
C10.16683 (17)1.0306 (4)0.72801 (17)0.0471 (6)
C20.19662 (18)0.8287 (4)0.77798 (18)0.0506 (6)
H20.14770.72030.77860.061*
C30.30013 (17)0.7894 (4)0.82716 (17)0.0455 (5)
H30.32060.65360.86130.055*
C40.37479 (16)0.9498 (4)0.82652 (15)0.0373 (5)
C50.34133 (17)1.1524 (4)0.77519 (15)0.0426 (5)
H50.38971.26200.77410.051*
C60.23803 (18)1.1938 (4)0.72600 (16)0.0462 (6)
H60.21681.32950.69200.055*
C70.48612 (16)0.9089 (4)0.87590 (15)0.0374 (5)
C80.52260 (19)0.6694 (4)0.9082 (2)0.0532 (7)
H8B0.528 (2)0.559 (5)0.8487 (17)0.064*
H8A0.4771 (19)0.591 (5)0.9251 (18)0.064*
C90.68859 (16)0.8209 (4)0.98249 (15)0.0404 (5)
C100.65597 (16)1.0233 (4)0.93059 (15)0.0379 (5)
C110.72987 (17)1.1812 (4)0.92807 (16)0.0448 (5)
H110.70951.31710.89400.054*
C120.83334 (18)1.1381 (4)0.97580 (17)0.0510 (6)
H120.88241.24370.97300.061*
C130.86396 (18)0.9383 (4)1.02769 (17)0.0525 (6)
H130.93370.91051.06020.063*
C140.79149 (17)0.7787 (4)1.03174 (17)0.0492 (6)
H140.81210.64491.06730.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0392 (4)0.0849 (6)0.0939 (6)0.0105 (3)0.0107 (3)0.0076 (4)
O0.0448 (9)0.0407 (9)0.0577 (10)0.0023 (7)0.0090 (7)0.0148 (8)
N0.0396 (10)0.0327 (10)0.0502 (10)0.0003 (8)0.0137 (8)0.0012 (8)
C10.0387 (11)0.0500 (14)0.0513 (13)0.0053 (10)0.0143 (10)0.0042 (11)
C20.0421 (12)0.0481 (14)0.0637 (15)0.0048 (10)0.0212 (11)0.0011 (12)
C30.0466 (12)0.0354 (12)0.0567 (14)0.0002 (9)0.0209 (10)0.0052 (10)
C40.0396 (11)0.0328 (11)0.0397 (11)0.0004 (9)0.0143 (9)0.0018 (9)
C50.0452 (12)0.0348 (12)0.0472 (12)0.0030 (9)0.0155 (10)0.0000 (10)
C60.0498 (13)0.0386 (13)0.0472 (13)0.0076 (10)0.0131 (10)0.0042 (10)
C70.0427 (11)0.0316 (11)0.0392 (11)0.0003 (9)0.0159 (9)0.0010 (9)
C80.0414 (13)0.0386 (13)0.0690 (16)0.0036 (10)0.0063 (11)0.0154 (12)
C90.0426 (12)0.0359 (11)0.0418 (11)0.0021 (9)0.0139 (9)0.0018 (9)
C100.0395 (11)0.0329 (11)0.0407 (11)0.0003 (9)0.0133 (9)0.0035 (9)
C110.0470 (12)0.0362 (12)0.0505 (13)0.0050 (10)0.0163 (10)0.0009 (10)
C120.0438 (12)0.0509 (14)0.0565 (14)0.0104 (11)0.0154 (10)0.0052 (11)
C130.0377 (12)0.0593 (16)0.0536 (14)0.0012 (11)0.0077 (10)0.0062 (12)
C140.0473 (13)0.0452 (13)0.0489 (13)0.0051 (11)0.0091 (10)0.0043 (11)
Geometric parameters (Å, º) top
Cl—C11.738 (2)C6—H60.9300
O—C91.373 (3)C7—C81.506 (3)
O—C81.423 (3)C8—H8B1.12 (2)
N—C71.283 (3)C8—H8A0.88 (2)
N—C101.413 (3)C9—C141.377 (3)
C1—C21.377 (4)C9—C101.397 (3)
C1—C61.379 (3)C10—C111.388 (3)
C2—C31.381 (3)C11—C121.381 (3)
C2—H20.9300C11—H110.9300
C3—C41.398 (3)C12—C131.380 (4)
C3—H30.9300C12—H120.9300
C4—C51.396 (3)C13—C141.386 (3)
C4—C71.476 (3)C13—H130.9300
C5—C61.380 (3)C14—H140.9300
C5—H50.9300
C9—O—C8114.05 (17)O—C8—H8B111.1 (14)
C7—N—C10117.16 (18)C7—C8—H8B113.0 (14)
C2—C1—C6121.5 (2)O—C8—H8A106.6 (18)
C2—C1—Cl119.59 (19)C7—C8—H8A112.1 (18)
C6—C1—Cl118.95 (19)H8B—C8—H8A101 (2)
C1—C2—C3119.1 (2)O—C9—C14119.3 (2)
C1—C2—H2120.4O—C9—C10119.36 (19)
C3—C2—H2120.4C14—C9—C10121.2 (2)
C2—C3—C4121.2 (2)C11—C10—C9118.6 (2)
C2—C3—H3119.4C11—C10—N119.95 (19)
C4—C3—H3119.4C9—C10—N121.42 (19)
C5—C4—C3117.9 (2)C12—C11—C10120.5 (2)
C5—C4—C7119.81 (19)C12—C11—H11119.8
C3—C4—C7122.3 (2)C10—C11—H11119.8
C6—C5—C4121.4 (2)C11—C12—C13120.0 (2)
C6—C5—H5119.3C11—C12—H12120.0
C4—C5—H5119.3C13—C12—H12120.0
C1—C6—C5119.0 (2)C12—C13—C14120.5 (2)
C1—C6—H6120.5C12—C13—H13119.8
C5—C6—H6120.5C14—C13—H13119.8
N—C7—C4119.60 (19)C9—C14—C13119.1 (2)
N—C7—C8121.3 (2)C9—C14—H14120.4
C4—C7—C8118.91 (19)C13—C14—H14120.4
O—C8—C7112.6 (2)
C6—C1—C2—C30.0 (4)N—C7—C8—O31.7 (3)
Cl—C1—C2—C3179.41 (18)C4—C7—C8—O153.0 (2)
C1—C2—C3—C40.4 (4)C8—O—C9—C14154.5 (2)
C2—C3—C4—C50.6 (3)C8—O—C9—C1028.8 (3)
C2—C3—C4—C7178.0 (2)O—C9—C10—C11177.76 (19)
C3—C4—C5—C60.4 (3)C14—C9—C10—C111.1 (3)
C7—C4—C5—C6178.2 (2)O—C9—C10—N0.6 (3)
C2—C1—C6—C50.1 (4)C14—C9—C10—N176.1 (2)
Cl—C1—C6—C5179.24 (17)C7—N—C10—C11169.0 (2)
C4—C5—C6—C10.0 (3)C7—N—C10—C913.9 (3)
C10—N—C7—C4178.47 (18)C9—C10—C11—C120.1 (3)
C10—N—C7—C83.1 (3)N—C10—C11—C12177.4 (2)
C5—C4—C7—N11.5 (3)C10—C11—C12—C130.9 (4)
C3—C4—C7—N170.0 (2)C11—C12—C13—C140.5 (4)
C5—C4—C7—C8164.0 (2)O—C9—C14—C13178.2 (2)
C3—C4—C7—C814.5 (3)C10—C9—C14—C131.5 (3)
C9—O—C8—C743.0 (3)C12—C13—C14—C90.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···Oi0.88 (2)2.60 (2)3.465 (3)166 (2)
Symmetry code: (i) x+1, y+1, z+2.
 

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