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The title compound, C19H24ClNO2, is isomeric with the 1-[(2-chloro-3,4-dimethoxy­benzyl­idene)amino]adamantane structure reported in the previous paper [Isik, Köysal, Septioglu & Çalis (2005). Acta Cryst. E61, o1851-o1852].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805015692/fl6163sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805015692/fl6163Isup2.hkl
Contains datablock I

CCDC reference: 258961

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.125
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT480_ALERT_4_C Long H...A H-Bond Reported H17A .. CL1 .. 2.94 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H14A .. CG1 .. 2.93 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 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 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

2-[(2-chloro-3,4-dimethoxybenzylidene)amino]adamantane top
Crystal data top
C19H24ClNO2F(000) = 712
Mr = 333.86Dx = 1.290 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 12884 reflections
a = 14.2591 (11) Åθ = 1.5–27.5°
b = 9.9334 (5) ŵ = 0.23 mm1
c = 12.7325 (10) ÅT = 293 K
β = 107.610 (6)°Prism, colourless
V = 1718.9 (2) Å30.80 × 0.42 × 0.12 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
3371 independent reflections
Radiation source: fine-focus sealed tube2604 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.068
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.5°
Ω scansh = 1716
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1112
Tmin = 0.898, Tmax = 0.964l = 1515
11934 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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0763P)2 + 0.0027P]
where P = (Fo2 + 2Fc2)/3
3371 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.32 e Å3
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
C180.55476 (17)0.0060 (2)0.8333 (2)0.0900 (7)
H18A0.51520.00390.88240.135*
H18B0.60620.07130.85890.135*
H18C0.51440.02990.76070.135*
C190.47684 (15)0.1894 (3)0.50040 (17)0.0812 (6)
H19A0.40660.19510.48350.122*
H19B0.49320.12040.45610.122*
H19C0.50220.27420.48510.122*
C20.75931 (12)0.12090 (14)0.81131 (12)0.0469 (4)
C30.65787 (12)0.12821 (15)0.76490 (13)0.0500 (4)
C40.61896 (12)0.14685 (17)0.65194 (14)0.0525 (4)
C50.68116 (12)0.15269 (18)0.58674 (13)0.0551 (4)
H50.65530.16350.51090.066*
C60.78099 (12)0.14244 (16)0.63462 (13)0.0515 (4)
H60.82180.14560.58980.062*
C10.82330 (11)0.12749 (14)0.74744 (12)0.0458 (3)
C70.93132 (12)0.12594 (15)0.79430 (13)0.0484 (4)
H70.96000.13740.86970.058*
C81.09117 (11)0.12276 (16)0.78029 (12)0.0500 (4)
H81.10830.13180.86050.060*
C151.12403 (12)0.24865 (16)0.73182 (14)0.0562 (4)
H151.09000.32760.74880.067*
C161.09953 (14)0.2341 (2)0.60685 (15)0.0683 (5)
H16A1.02910.22360.57420.082*
H16B1.11980.31450.57630.082*
C111.15222 (14)0.1124 (2)0.57975 (14)0.0671 (5)
H111.13620.10330.49960.081*
C121.26289 (15)0.1314 (2)0.63010 (16)0.0707 (5)
H12A1.28380.21160.59990.085*
H12B1.29740.05480.61210.085*
C131.28809 (13)0.14467 (19)0.75510 (15)0.0591 (4)
H131.35930.15590.78750.071*
C171.25487 (13)0.01895 (18)0.80195 (15)0.0611 (4)
H17A1.27120.02690.88140.073*
H17B1.28880.05910.78550.073*
C91.14378 (12)0.00101 (16)0.75171 (13)0.0528 (4)
H91.12290.08040.78200.063*
C101.11964 (14)0.01339 (19)0.62733 (15)0.0627 (4)
H10A1.15310.09150.61020.075*
H10B1.04940.02630.59470.075*
C141.23511 (13)0.26620 (18)0.78330 (16)0.0633 (5)
H14A1.25660.34750.75520.076*
H14B1.25080.27460.86260.076*
N10.98483 (10)0.10937 (14)0.73346 (11)0.0556 (3)
O10.59689 (10)0.12317 (13)0.83040 (11)0.0659 (3)
O20.51893 (9)0.15739 (14)0.61334 (11)0.0691 (4)
Cl10.80551 (3)0.09987 (5)0.95260 (3)0.06582 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C180.0842 (16)0.0892 (16)0.1184 (19)0.0063 (12)0.0630 (14)0.0251 (13)
C190.0557 (10)0.1124 (18)0.0682 (12)0.0091 (11)0.0076 (8)0.0123 (11)
C20.0554 (9)0.0429 (8)0.0446 (8)0.0022 (6)0.0184 (6)0.0010 (6)
C30.0538 (9)0.0489 (8)0.0539 (8)0.0026 (7)0.0261 (7)0.0007 (6)
C40.0459 (8)0.0553 (9)0.0571 (9)0.0002 (7)0.0168 (7)0.0003 (7)
C50.0509 (9)0.0686 (10)0.0449 (8)0.0037 (8)0.0130 (7)0.0015 (7)
C60.0510 (9)0.0594 (9)0.0475 (8)0.0054 (7)0.0199 (7)0.0008 (6)
C10.0485 (8)0.0418 (7)0.0478 (8)0.0023 (6)0.0157 (6)0.0019 (6)
C70.0500 (9)0.0477 (8)0.0459 (8)0.0012 (7)0.0122 (6)0.0010 (6)
C80.0426 (8)0.0611 (9)0.0433 (8)0.0027 (7)0.0086 (6)0.0018 (6)
C150.0464 (8)0.0449 (8)0.0720 (10)0.0011 (7)0.0101 (7)0.0016 (7)
C160.0564 (10)0.0715 (12)0.0702 (11)0.0042 (9)0.0088 (8)0.0272 (9)
C110.0656 (11)0.0900 (14)0.0458 (9)0.0098 (10)0.0169 (8)0.0012 (8)
C120.0635 (11)0.0857 (13)0.0696 (12)0.0067 (10)0.0303 (9)0.0016 (9)
C130.0417 (8)0.0660 (10)0.0666 (10)0.0012 (8)0.0120 (7)0.0016 (8)
C170.0542 (10)0.0606 (10)0.0641 (10)0.0115 (8)0.0112 (7)0.0079 (8)
C90.0562 (9)0.0435 (8)0.0572 (9)0.0014 (7)0.0148 (7)0.0065 (6)
C100.0627 (11)0.0610 (10)0.0635 (10)0.0070 (8)0.0177 (8)0.0157 (8)
C140.0508 (9)0.0538 (10)0.0804 (12)0.0078 (8)0.0126 (8)0.0066 (8)
N10.0449 (7)0.0703 (9)0.0507 (7)0.0061 (6)0.0131 (6)0.0036 (6)
O10.0650 (8)0.0753 (8)0.0699 (8)0.0084 (6)0.0393 (6)0.0034 (6)
O20.0453 (6)0.0960 (10)0.0649 (8)0.0052 (6)0.0151 (5)0.0083 (6)
Cl10.0742 (3)0.0807 (3)0.0447 (2)0.0086 (2)0.02106 (19)0.00249 (18)
Geometric parameters (Å, º) top
C18—O11.422 (2)C8—H80.9800
C18—H18A0.9600C15—C161.529 (2)
C18—H18B0.9600C15—C141.530 (2)
C18—H18C0.9600C15—H150.9800
C19—O21.417 (2)C16—C111.517 (3)
C19—H19A0.9600C16—H16A0.9700
C19—H19B0.9600C16—H16B0.9700
C19—H19C0.9600C11—C101.522 (3)
C2—C31.389 (2)C11—C121.525 (3)
C2—C11.395 (2)C11—H110.9800
C2—Cl11.7310 (15)C12—C131.528 (3)
C3—O11.3759 (18)C12—H12A0.9700
C3—C41.389 (2)C12—H12B0.9700
C4—O21.365 (2)C13—C171.520 (3)
C4—C51.387 (2)C13—C141.523 (3)
C5—C61.372 (2)C13—H130.9800
C5—H50.9300C17—C91.529 (2)
C6—C11.388 (2)C17—H17A0.9700
C6—H60.9300C17—H17B0.9700
C1—C71.474 (2)C9—C101.522 (2)
C7—N11.252 (2)C9—H90.9800
C7—H70.9300C10—H10A0.9700
C8—N11.458 (2)C10—H10B0.9700
C8—C91.524 (2)C14—H14A0.9700
C8—C151.529 (2)C14—H14B0.9700
O1—C18—H18A109.5C11—C16—H16B109.7
O1—C18—H18B109.5C15—C16—H16B109.7
H18A—C18—H18B109.5H16A—C16—H16B108.2
O1—C18—H18C109.5C16—C11—C10109.39 (15)
H18A—C18—H18C109.5C16—C11—C12109.08 (16)
H18B—C18—H18C109.5C10—C11—C12109.62 (16)
O2—C19—H19A109.5C16—C11—H11109.6
O2—C19—H19B109.5C10—C11—H11109.6
H19A—C19—H19B109.5C12—C11—H11109.6
O2—C19—H19C109.5C11—C12—C13109.64 (14)
H19A—C19—H19C109.5C11—C12—H12A109.7
H19B—C19—H19C109.5C13—C12—H12A109.7
C3—C2—C1122.00 (14)C11—C12—H12B109.7
C3—C2—Cl1117.92 (11)C13—C12—H12B109.7
C1—C2—Cl1120.06 (13)H12A—C12—H12B108.2
O1—C3—C4120.33 (15)C17—C13—C14108.84 (15)
O1—C3—C2120.53 (15)C17—C13—C12109.55 (15)
C4—C3—C2119.07 (14)C14—C13—C12109.69 (15)
O2—C4—C5124.68 (15)C17—C13—H13109.6
O2—C4—C3115.45 (14)C14—C13—H13109.6
C5—C4—C3119.87 (15)C12—C13—H13109.6
C6—C5—C4119.74 (15)C13—C17—C9109.76 (13)
C6—C5—H5120.1C13—C17—H17A109.7
C4—C5—H5120.1C9—C17—H17A109.7
C5—C6—C1122.38 (15)C13—C17—H17B109.7
C5—C6—H6118.8C9—C17—H17B109.7
C1—C6—H6118.8H17A—C17—H17B108.2
C6—C1—C2116.89 (15)C10—C9—C8110.50 (13)
C6—C1—C7119.60 (14)C10—C9—C17109.01 (14)
C2—C1—C7123.44 (14)C8—C9—C17109.28 (13)
N1—C7—C1120.58 (14)C10—C9—H9109.3
N1—C7—H7119.7C8—C9—H9109.3
C1—C7—H7119.7C17—C9—H9109.3
N1—C8—C9110.86 (13)C11—C10—C9109.69 (13)
N1—C8—C15108.50 (13)C11—C10—H10A109.7
C9—C8—C15108.64 (13)C9—C10—H10A109.7
N1—C8—H8109.6C11—C10—H10B109.7
C9—C8—H8109.6C9—C10—H10B109.7
C15—C8—H8109.6H10A—C10—H10B108.2
C16—C15—C8109.94 (13)C13—C14—C15109.38 (14)
C16—C15—C14109.72 (15)C13—C14—H14A109.8
C8—C15—C14108.91 (13)C15—C14—H14A109.8
C16—C15—H15109.4C13—C14—H14B109.8
C8—C15—H15109.4C15—C14—H14B109.8
C14—C15—H15109.4H14A—C14—H14B108.2
C11—C16—C15109.83 (14)C7—N1—C8119.22 (14)
C11—C16—H16A109.7C3—O1—C18113.47 (14)
C15—C16—H16A109.7C4—O2—C19117.28 (14)
C1—C2—C3—O1179.14 (14)C16—C11—C12—C1360.43 (19)
Cl1—C2—C3—O12.1 (2)C10—C11—C12—C1359.3 (2)
C1—C2—C3—C42.0 (2)C11—C12—C13—C1759.2 (2)
Cl1—C2—C3—C4179.15 (12)C11—C12—C13—C1460.2 (2)
O1—C3—C4—O20.8 (2)C14—C13—C17—C960.16 (19)
C2—C3—C4—O2177.93 (14)C12—C13—C17—C959.78 (19)
O1—C3—C4—C5179.56 (15)N1—C8—C9—C1059.93 (16)
C2—C3—C4—C52.5 (2)C15—C8—C9—C1059.21 (16)
O2—C4—C5—C6179.26 (16)N1—C8—C9—C17179.88 (13)
C3—C4—C5—C61.2 (3)C15—C8—C9—C1760.74 (16)
C4—C5—C6—C10.6 (3)C13—C17—C9—C1060.22 (18)
C5—C6—C1—C21.1 (2)C13—C17—C9—C860.63 (18)
C5—C6—C1—C7176.03 (15)C16—C11—C10—C959.42 (19)
C3—C2—C1—C60.3 (2)C12—C11—C10—C960.13 (19)
Cl1—C2—C1—C6179.08 (11)C8—C9—C10—C1159.84 (19)
C3—C2—C1—C7177.27 (14)C17—C9—C10—C1160.27 (18)
Cl1—C2—C1—C74.0 (2)C17—C13—C14—C1560.64 (19)
C6—C1—C7—N115.2 (2)C12—C13—C14—C1559.21 (19)
C2—C1—C7—N1167.95 (15)C16—C15—C14—C1358.90 (19)
N1—C8—C15—C1661.58 (17)C8—C15—C14—C1361.48 (19)
C9—C8—C15—C1659.02 (16)C1—C7—N1—C8173.44 (14)
N1—C8—C15—C14178.17 (13)C9—C8—N1—C7129.10 (15)
C9—C8—C15—C1461.23 (17)C15—C8—N1—C7111.68 (16)
C8—C15—C16—C1160.00 (18)C4—C3—O1—C1883.2 (2)
C14—C15—C16—C1159.76 (18)C2—C3—O1—C1899.71 (19)
C15—C16—C11—C1059.67 (19)C5—C4—O2—C196.3 (3)
C15—C16—C11—C1260.22 (18)C3—C4—O2—C19174.08 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17A···Cl1i0.972.943.6784 (19)134
C14—H14A···Cg1ii0.972.933.7274 (19)141
Symmetry codes: (i) x+2, y, z+2; (ii) x, y1/2, z+1/2.
 

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