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In the mol­ecule of the title compound, C13H16ClNO3, the N-containing ring is not planar and has a flattened boat form. Inter­molecular C—H...O hydrogen bonds link the mol­ecules to form infinite chains and may be effective in the stabilization of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021374/hk2054sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021374/hk2054Isup2.hkl
Contains datablock I

CCDC reference: 613722

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.053
  • wR factor = 0.141
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; 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: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

2-(2-Chloroacetyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline top
Crystal data top
C13H16ClNO3F(000) = 568
Mr = 269.72Dx = 1.405 Mg m3
Monoclinic, P21/aMelting point: 386(2) K
Hall symbol: -P 2yabMo Kα radiation, λ = 0.71073 Å
a = 8.6561 (9) ÅCell parameters from 25 reflections
b = 17.7944 (18) Åθ = 10–12°
c = 9.3090 (11) ŵ = 0.30 mm1
β = 117.22 (3)°T = 296 K
V = 1275.1 (4) Å3Block, colourless
Z = 40.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD4
diffractometer
1541 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 26.0°, θmin = 2.3°
ω/2θ scansh = 010
Absorption correction: ψ scan
(North et al., 1968)
k = 021
Tmin = 0.916, Tmax = 0.971l = 1110
2662 measured reflections3 standard reflections every 200 reflections
2496 independent reflections intensity decay: 1%
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.06P)2 + 0.34P]
where P = (Fo2 + 2Fc2)/3
2496 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.24 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
Cl0.54986 (12)0.24874 (5)0.97799 (11)0.0576 (3)
O10.7888 (3)0.11335 (12)0.2320 (2)0.0490 (6)
O20.9652 (3)0.16799 (11)0.5174 (2)0.0468 (6)
O30.7147 (3)0.10690 (12)0.9781 (3)0.0511 (6)
N0.7135 (3)0.11279 (13)0.7368 (3)0.0397 (6)
C10.7051 (5)0.08097 (19)0.0730 (4)0.0542 (9)
H1A0.71810.11400.00220.081*
H1B0.75740.03330.07360.081*
H1C0.58380.07400.04140.081*
C21.0760 (5)0.19690 (19)0.6745 (4)0.0568 (9)
H2A1.12820.24290.66460.085*
H2B1.00890.20630.73110.085*
H2C1.16520.16090.73360.085*
C30.8807 (4)0.10201 (16)0.5103 (3)0.0363 (7)
C40.7829 (4)0.07232 (16)0.3542 (3)0.0382 (7)
C50.6928 (4)0.00669 (17)0.3350 (4)0.0400 (7)
H5A0.62700.01240.23160.048*
C60.6977 (4)0.03213 (16)0.4674 (4)0.0372 (7)
C70.6028 (4)0.10528 (17)0.4455 (4)0.0440 (8)
H7A0.48510.09570.42790.053*
H7B0.59670.13130.35160.053*
C80.6964 (4)0.15373 (17)0.5941 (4)0.0448 (8)
H8A0.81070.16690.60660.054*
H8B0.63180.19980.58220.054*
C90.8067 (5)0.04138 (18)0.7699 (4)0.0495 (8)
H9A0.76010.00790.82270.059*
H9B0.92810.05020.84400.059*
C100.7948 (4)0.00340 (16)0.6203 (3)0.0350 (7)
C110.8869 (4)0.06378 (16)0.6414 (4)0.0380 (7)
H11A0.95280.08280.74490.046*
C120.6767 (4)0.14073 (17)0.8524 (4)0.0385 (7)
C130.5785 (4)0.21449 (17)0.8127 (4)0.0447 (8)
H13A0.46570.20750.72030.054*
H13B0.64180.25140.78370.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0685 (6)0.0535 (5)0.0576 (5)0.0147 (5)0.0347 (5)0.0034 (5)
O10.0686 (15)0.0410 (12)0.0319 (12)0.0095 (11)0.0183 (11)0.0008 (10)
O20.0585 (14)0.0384 (12)0.0376 (12)0.0142 (11)0.0169 (11)0.0031 (10)
O30.0702 (16)0.0464 (13)0.0396 (13)0.0116 (12)0.0275 (12)0.0050 (11)
N0.0486 (15)0.0325 (13)0.0407 (15)0.0053 (11)0.0227 (13)0.0032 (11)
C10.080 (3)0.049 (2)0.0350 (18)0.0073 (18)0.0270 (18)0.0010 (16)
C20.068 (2)0.0443 (19)0.046 (2)0.0189 (18)0.0155 (18)0.0055 (16)
C30.0355 (16)0.0318 (16)0.0387 (17)0.0011 (13)0.0144 (14)0.0001 (13)
C40.0449 (18)0.0349 (16)0.0336 (16)0.0041 (14)0.0170 (14)0.0030 (13)
C50.0440 (18)0.0389 (17)0.0311 (16)0.0012 (14)0.0119 (14)0.0015 (13)
C60.0366 (17)0.0353 (16)0.0402 (17)0.0002 (13)0.0180 (14)0.0039 (14)
C70.0475 (19)0.0406 (17)0.0388 (17)0.0060 (15)0.0153 (15)0.0064 (14)
C80.058 (2)0.0350 (16)0.0491 (19)0.0009 (15)0.0309 (17)0.0046 (15)
C90.058 (2)0.0468 (19)0.0413 (18)0.0154 (17)0.0202 (17)0.0028 (16)
C100.0371 (17)0.0343 (16)0.0360 (16)0.0026 (13)0.0189 (14)0.0013 (13)
C110.0426 (18)0.0375 (16)0.0308 (15)0.0029 (14)0.0141 (14)0.0021 (13)
C120.0415 (17)0.0353 (16)0.0391 (17)0.0039 (13)0.0189 (14)0.0024 (14)
C130.051 (2)0.0413 (18)0.0460 (18)0.0052 (15)0.0255 (16)0.0003 (15)
Geometric parameters (Å, º) top
Cl—C131.774 (3)C5—C61.397 (4)
O1—C41.372 (3)C5—H5A0.9300
O1—C11.438 (3)C6—C101.379 (4)
O2—C31.369 (3)C6—C71.502 (4)
O2—C21.428 (4)C7—C81.512 (4)
O3—C121.220 (3)C7—H7A0.9700
N—C121.349 (4)C7—H7B0.9700
N—C91.460 (4)C8—H8A0.9700
N—C81.463 (4)C8—H8B0.9700
C1—H1A0.9600C9—C101.508 (4)
C1—H1B0.9600C9—H9A0.9700
C1—H1C0.9600C9—H9B0.9700
C2—H2A0.9600C10—C111.400 (4)
C2—H2B0.9600C11—H11A0.9300
C2—H2C0.9600C12—C131.515 (4)
C3—C111.377 (4)C13—H13A0.9700
C3—C41.408 (4)C13—H13B0.9700
C4—C51.370 (4)
C4—O1—C1116.6 (2)C8—C7—H7A109.7
C3—O2—C2116.9 (2)C6—C7—H7B109.7
C12—N—C9117.5 (2)C8—C7—H7B109.7
C12—N—C8125.3 (3)H7A—C7—H7B108.2
C9—N—C8116.2 (2)N—C8—C7109.6 (2)
O1—C1—H1A109.5N—C8—H8A109.7
O1—C1—H1B109.5C7—C8—H8A109.7
H1A—C1—H1B109.5N—C8—H8B109.7
O1—C1—H1C109.5C7—C8—H8B109.7
H1A—C1—H1C109.5H8A—C8—H8B108.2
H1B—C1—H1C109.5N—C9—C10113.4 (2)
O2—C2—H2A109.5N—C9—H9A108.9
O2—C2—H2B109.5C10—C9—H9A108.9
H2A—C2—H2B109.5N—C9—H9B108.9
O2—C2—H2C109.5C10—C9—H9B108.9
H2A—C2—H2C109.5H9A—C9—H9B107.7
H2B—C2—H2C109.5C6—C10—C11120.0 (3)
O2—C3—C11125.3 (3)C6—C10—C9122.6 (3)
O2—C3—C4115.3 (3)C11—C10—C9117.3 (3)
C11—C3—C4119.4 (3)C3—C11—C10120.6 (3)
O1—C4—C5125.5 (3)C3—C11—H11A119.7
O1—C4—C3115.0 (3)C10—C11—H11A119.7
C5—C4—C3119.5 (3)O3—C12—N121.6 (3)
C4—C5—C6121.4 (3)O3—C12—C13122.5 (3)
C4—C5—H5A119.3N—C12—C13115.9 (3)
C6—C5—H5A119.3C12—C13—Cl111.8 (2)
C10—C6—C5119.1 (3)C12—C13—H13A109.3
C10—C6—C7119.9 (3)Cl—C13—H13A109.3
C5—C6—C7121.0 (3)C12—C13—H13B109.3
C6—C7—C8109.8 (2)Cl—C13—H13B109.3
C6—C7—H7A109.7H13A—C13—H13B107.9
C2—O2—C3—C113.7 (4)C8—N—C9—C1028.0 (4)
C2—O2—C3—C4175.5 (3)C5—C6—C10—C110.0 (4)
C1—O1—C4—C55.5 (4)C7—C6—C10—C11178.4 (3)
C1—O1—C4—C3173.9 (3)C5—C6—C10—C9179.7 (3)
O2—C3—C4—O11.0 (4)C7—C6—C10—C91.9 (4)
C11—C3—C4—O1178.2 (3)N—C9—C10—C63.1 (4)
O2—C3—C4—C5179.5 (3)N—C9—C10—C11177.2 (3)
C11—C3—C4—C51.2 (4)O2—C3—C11—C10179.9 (3)
O1—C4—C5—C6178.5 (3)C4—C3—C11—C101.0 (4)
C3—C4—C5—C60.9 (4)C6—C10—C11—C30.4 (4)
C4—C5—C6—C100.3 (4)C9—C10—C11—C3179.3 (3)
C4—C5—C6—C7178.1 (3)C9—N—C12—O32.1 (4)
C10—C6—C7—C827.9 (4)C8—N—C12—O3170.5 (3)
C5—C6—C7—C8150.5 (3)C9—N—C12—C13179.4 (3)
C12—N—C8—C7132.7 (3)C8—N—C12—C1312.2 (4)
C9—N—C8—C758.7 (3)O3—C12—C13—Cl6.5 (4)
C6—C7—C8—N56.4 (3)N—C12—C13—Cl176.2 (2)
C12—N—C9—C10162.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1C···O3i0.962.573.473 (5)156
C2—H2C···O3ii0.962.583.308 (4)133
C8—H8B···O2iii0.972.533.431 (4)155
C13—H13B···O1iii0.972.503.364 (4)148
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y, z+2; (iii) x+3/2, y+1/2, z+1.
 

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