2-(2-Chloro­acet­yl)-6,7-dimeth­oxy-1,2,3,4-tetra­hydro­isoquinoline

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.

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

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

Crystal data

C13H16ClNO3	F(000) = 568
Mr = 269.72	Dx = 1.405 Mg m^−3
Monoclinic, P21/a	Melting point: 386(2) K
Hall symbol: -P 2yab	Mo Kα radiation, λ = 0.71073 Å
a = 8.6561 (9) Å	Cell parameters from 25 reflections
b = 17.7944 (18) Å	θ = 10–12°
c = 9.3090 (11) Å	µ = 0.30 mm^−1
β = 117.22 (3)°	T = 296 K
V = 1275.1 (4) Å^3	Block, colourless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD4 diffractometer	1541 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 26.0°, θmin = 2.3°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→21
Tmin = 0.916, Tmax = 0.971	l = −11→10
2662 measured reflections	3 standard reflections every 200 reflections
2496 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.06P)^2 + 0.34P] where P = (Fo^2 + 2Fc^2)/3
2496 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl	0.54986 (12)	0.24874 (5)	0.97799 (11)	0.0576 (3)
O1	0.7888 (3)	−0.11335 (12)	0.2320 (2)	0.0490 (6)
O2	0.9652 (3)	−0.16799 (11)	0.5174 (2)	0.0468 (6)
O3	0.7147 (3)	0.10690 (12)	0.9781 (3)	0.0511 (6)
N	0.7135 (3)	0.11279 (13)	0.7368 (3)	0.0397 (6)
C1	0.7051 (5)	−0.08097 (19)	0.0730 (4)	0.0542 (9)
H1A	0.7181	−0.1140	−0.0022	0.081*
H1B	0.7574	−0.0333	0.0736	0.081*
H1C	0.5838	−0.0740	0.0414	0.081*
C2	1.0760 (5)	−0.19690 (19)	0.6745 (4)	0.0568 (9)
H2A	1.1282	−0.2429	0.6646	0.085*
H2B	1.0089	−0.2063	0.7311	0.085*
H2C	1.1652	−0.1609	0.7336	0.085*
C3	0.8807 (4)	−0.10201 (16)	0.5103 (3)	0.0363 (7)
C4	0.7829 (4)	−0.07232 (16)	0.3542 (3)	0.0382 (7)
C5	0.6928 (4)	−0.00669 (17)	0.3350 (4)	0.0400 (7)
H5A	0.6270	0.0124	0.2316	0.048*
C6	0.6977 (4)	0.03213 (16)	0.4674 (4)	0.0372 (7)
C7	0.6028 (4)	0.10528 (17)	0.4455 (4)	0.0440 (8)
H7A	0.4851	0.0957	0.4279	0.053*
H7B	0.5967	0.1313	0.3516	0.053*
C8	0.6964 (4)	0.15373 (17)	0.5941 (4)	0.0448 (8)
H8A	0.8107	0.1669	0.6066	0.054*
H8B	0.6318	0.1998	0.5822	0.054*
C9	0.8067 (5)	0.04138 (18)	0.7699 (4)	0.0495 (8)
H9A	0.7601	0.0079	0.8227	0.059*
H9B	0.9281	0.0502	0.8440	0.059*
C10	0.7948 (4)	0.00340 (16)	0.6203 (3)	0.0350 (7)
C11	0.8869 (4)	−0.06378 (16)	0.6414 (4)	0.0380 (7)
H11A	0.9528	−0.0828	0.7449	0.046*
C12	0.6767 (4)	0.14073 (17)	0.8524 (4)	0.0385 (7)
C13	0.5785 (4)	0.21449 (17)	0.8127 (4)	0.0447 (8)
H13A	0.4657	0.2075	0.7203	0.054*
H13B	0.6418	0.2514	0.7837	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0685 (6)	0.0535 (5)	0.0576 (5)	0.0147 (5)	0.0347 (5)	−0.0034 (5)
O1	0.0686 (15)	0.0410 (12)	0.0319 (12)	0.0095 (11)	0.0183 (11)	0.0008 (10)
O2	0.0585 (14)	0.0384 (12)	0.0376 (12)	0.0142 (11)	0.0169 (11)	0.0031 (10)
O3	0.0702 (16)	0.0464 (13)	0.0396 (13)	0.0116 (12)	0.0275 (12)	0.0050 (11)
N	0.0486 (15)	0.0325 (13)	0.0407 (15)	0.0053 (11)	0.0227 (13)	0.0032 (11)
C1	0.080 (3)	0.049 (2)	0.0350 (18)	0.0073 (18)	0.0270 (18)	0.0010 (16)
C2	0.068 (2)	0.0443 (19)	0.046 (2)	0.0189 (18)	0.0155 (18)	0.0055 (16)
C3	0.0355 (16)	0.0318 (16)	0.0387 (17)	0.0011 (13)	0.0144 (14)	−0.0001 (13)
C4	0.0449 (18)	0.0349 (16)	0.0336 (16)	−0.0041 (14)	0.0170 (14)	−0.0030 (13)
C5	0.0440 (18)	0.0389 (17)	0.0311 (16)	0.0012 (14)	0.0119 (14)	0.0015 (13)
C6	0.0366 (17)	0.0353 (16)	0.0402 (17)	0.0002 (13)	0.0180 (14)	0.0039 (14)
C7	0.0475 (19)	0.0406 (17)	0.0388 (17)	0.0060 (15)	0.0153 (15)	0.0064 (14)
C8	0.058 (2)	0.0350 (16)	0.0491 (19)	0.0009 (15)	0.0309 (17)	0.0046 (15)
C9	0.058 (2)	0.0468 (19)	0.0413 (18)	0.0154 (17)	0.0202 (17)	0.0028 (16)
C10	0.0371 (17)	0.0343 (16)	0.0360 (16)	−0.0026 (13)	0.0189 (14)	−0.0013 (13)
C11	0.0426 (18)	0.0375 (16)	0.0308 (15)	0.0029 (14)	0.0141 (14)	0.0021 (13)
C12	0.0415 (17)	0.0353 (16)	0.0391 (17)	−0.0039 (13)	0.0189 (14)	−0.0024 (14)
C13	0.051 (2)	0.0413 (18)	0.0460 (18)	0.0052 (15)	0.0255 (16)	−0.0003 (15)

Geometric parameters (Å, º)

Cl—C13	1.774 (3)	C5—C6	1.397 (4)
O1—C4	1.372 (3)	C5—H5A	0.9300
O1—C1	1.438 (3)	C6—C10	1.379 (4)
O2—C3	1.369 (3)	C6—C7	1.502 (4)
O2—C2	1.428 (4)	C7—C8	1.512 (4)
O3—C12	1.220 (3)	C7—H7A	0.9700
N—C12	1.349 (4)	C7—H7B	0.9700
N—C9	1.460 (4)	C8—H8A	0.9700
N—C8	1.463 (4)	C8—H8B	0.9700
C1—H1A	0.9600	C9—C10	1.508 (4)
C1—H1B	0.9600	C9—H9A	0.9700
C1—H1C	0.9600	C9—H9B	0.9700
C2—H2A	0.9600	C10—C11	1.400 (4)
C2—H2B	0.9600	C11—H11A	0.9300
C2—H2C	0.9600	C12—C13	1.515 (4)
C3—C11	1.377 (4)	C13—H13A	0.9700
C3—C4	1.408 (4)	C13—H13B	0.9700
C4—C5	1.370 (4)
C4—O1—C1	116.6 (2)	C8—C7—H7A	109.7
C3—O2—C2	116.9 (2)	C6—C7—H7B	109.7
C12—N—C9	117.5 (2)	C8—C7—H7B	109.7
C12—N—C8	125.3 (3)	H7A—C7—H7B	108.2
C9—N—C8	116.2 (2)	N—C8—C7	109.6 (2)
O1—C1—H1A	109.5	N—C8—H8A	109.7
O1—C1—H1B	109.5	C7—C8—H8A	109.7
H1A—C1—H1B	109.5	N—C8—H8B	109.7
O1—C1—H1C	109.5	C7—C8—H8B	109.7
H1A—C1—H1C	109.5	H8A—C8—H8B	108.2
H1B—C1—H1C	109.5	N—C9—C10	113.4 (2)
O2—C2—H2A	109.5	N—C9—H9A	108.9
O2—C2—H2B	109.5	C10—C9—H9A	108.9
H2A—C2—H2B	109.5	N—C9—H9B	108.9
O2—C2—H2C	109.5	C10—C9—H9B	108.9
H2A—C2—H2C	109.5	H9A—C9—H9B	107.7
H2B—C2—H2C	109.5	C6—C10—C11	120.0 (3)
O2—C3—C11	125.3 (3)	C6—C10—C9	122.6 (3)
O2—C3—C4	115.3 (3)	C11—C10—C9	117.3 (3)
C11—C3—C4	119.4 (3)	C3—C11—C10	120.6 (3)
O1—C4—C5	125.5 (3)	C3—C11—H11A	119.7
O1—C4—C3	115.0 (3)	C10—C11—H11A	119.7
C5—C4—C3	119.5 (3)	O3—C12—N	121.6 (3)
C4—C5—C6	121.4 (3)	O3—C12—C13	122.5 (3)
C4—C5—H5A	119.3	N—C12—C13	115.9 (3)
C6—C5—H5A	119.3	C12—C13—Cl	111.8 (2)
C10—C6—C5	119.1 (3)	C12—C13—H13A	109.3
C10—C6—C7	119.9 (3)	Cl—C13—H13A	109.3
C5—C6—C7	121.0 (3)	C12—C13—H13B	109.3
C6—C7—C8	109.8 (2)	Cl—C13—H13B	109.3
C6—C7—H7A	109.7	H13A—C13—H13B	107.9
C2—O2—C3—C11	−3.7 (4)	C8—N—C9—C10	−28.0 (4)
C2—O2—C3—C4	175.5 (3)	C5—C6—C10—C11	0.0 (4)
C1—O1—C4—C5	5.5 (4)	C7—C6—C10—C11	−178.4 (3)
C1—O1—C4—C3	−173.9 (3)	C5—C6—C10—C9	−179.7 (3)
O2—C3—C4—O1	−1.0 (4)	C7—C6—C10—C9	1.9 (4)
C11—C3—C4—O1	178.2 (3)	N—C9—C10—C6	−3.1 (4)
O2—C3—C4—C5	179.5 (3)	N—C9—C10—C11	177.2 (3)
C11—C3—C4—C5	−1.2 (4)	O2—C3—C11—C10	−179.9 (3)
O1—C4—C5—C6	−178.5 (3)	C4—C3—C11—C10	1.0 (4)
C3—C4—C5—C6	0.9 (4)	C6—C10—C11—C3	−0.4 (4)
C4—C5—C6—C10	−0.3 (4)	C9—C10—C11—C3	179.3 (3)
C4—C5—C6—C7	178.1 (3)	C9—N—C12—O3	−2.1 (4)
C10—C6—C7—C8	27.9 (4)	C8—N—C12—O3	−170.5 (3)
C5—C6—C7—C8	−150.5 (3)	C9—N—C12—C13	−179.4 (3)
C12—N—C8—C7	−132.7 (3)	C8—N—C12—C13	12.2 (4)
C9—N—C8—C7	58.7 (3)	O3—C12—C13—Cl	6.5 (4)
C6—C7—C8—N	−56.4 (3)	N—C12—C13—Cl	−176.2 (2)
C12—N—C9—C10	162.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···O3^i	0.96	2.57	3.473 (5)	156
C2—H2C···O3^ii	0.96	2.58	3.308 (4)	133
C8—H8B···O2^iii	0.97	2.53	3.431 (4)	155
C13—H13B···O1^iii	0.97	2.50	3.364 (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.