6,7-Dimeth-oxy-3-meth-oxy-carbonyl-1-(2-meth-oxy-phen-yl)-3,4-dihydro-isoquinoline 2-oxide.

In the title compound, C(20)H(21)NO(6), an N-oxide-based organocatalyst, the N-containing six-membered ring adopts a twisted half-chair conformation. No hydrogen bonding or π-π stacking was found within the crystal structure.

Related literature

For related structures, see: Naicker et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C20H21NO6

M = 371.38

Monoclinic,

a = 5.4765 (1) Å

b = 21.9984 (6) Å

c = 15.0007 (4) Å

β = 92.774 (2)°

V = 1805.08 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.25 × 0.18 × 0.15 mm

Data collection

Bruker APEXII diffractometer

7815 measured reflections

3959 independent reflections

3092 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.157

S = 1.06

3959 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.92 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016539/hg5031sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016539/hg5031Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016539/hg5031Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H21NO6	F(000) = 784
Mr = 371.38	Dx = 1.367 Mg m−3
Monoclinic, P21/n	Melting point: 423 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.4765 (1) Å	Cell parameters from 7815 reflections
b = 21.9984 (6) Å	θ = 2.3–27.1°
c = 15.0007 (4) Å	µ = 0.10 mm−1
β = 92.774 (2)°	T = 173 K
V = 1805.08 (8) Å3	Block, colourless
Z = 4	0.25 × 0.18 × 0.15 mm

Bruker APEXII diffractometer	3092 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
graphite	θmax = 27.1°, θmin = 2.3°
1.2° φ and ω scans	h = −7→7
7815 measured reflections	k = −28→28
3959 independent reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H-atom parameters constrained
wR(F2) = 0.157	w = 1/[σ2(Fo2) + (0.080P)2 + 1.0977P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3959 reflections	Δρmax = 0.92 e Å−3
245 parameters	Δρmin = −0.33 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0055 (19)

Experimental. Half sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 30 mm; combination of φ and ω scans of 1.0°, 40 s per °, 2 iterations.

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.

	x	y	z	Uiso*/Ueq
O1	0.2176 (3)	0.22907 (6)	0.35593 (9)	0.0354 (3)
O2	0.6006 (2)	−0.03624 (6)	0.11617 (9)	0.0322 (3)
O3	0.2824 (3)	−0.10179 (6)	0.19301 (9)	0.0344 (3)
O4	0.5317 (3)	0.12825 (8)	0.45676 (10)	0.0441 (4)
O5	0.2474 (3)	0.07631 (8)	0.52628 (10)	0.0485 (4)
O6	0.2093 (3)	0.16305 (7)	0.07924 (9)	0.0391 (4)
N1	0.2146 (3)	0.17212 (7)	0.33291 (10)	0.0251 (3)
C1	0.3125 (3)	0.14938 (8)	0.26149 (11)	0.0246 (4)
C2	0.3023 (3)	0.08366 (8)	0.24573 (11)	0.0228 (4)
C3	0.4608 (3)	0.05630 (8)	0.18643 (11)	0.0247 (4)
H3	0.5749	0.0806	0.1567	0.030*
C4	0.4517 (3)	−0.00558 (8)	0.17115 (11)	0.0246 (4)
C5	0.2793 (3)	−0.04178 (8)	0.21365 (12)	0.0260 (4)
C6	0.1259 (3)	−0.01473 (8)	0.27287 (12)	0.0262 (4)
H6	0.0115	−0.0390	0.3025	0.031*
C7	0.1370 (3)	0.04758 (8)	0.28959 (11)	0.0238 (4)
C8	−0.0255 (3)	0.07830 (8)	0.35355 (12)	0.0283 (4)
H8A	−0.0748	0.0488	0.3991	0.034*
H8B	−0.1752	0.0932	0.3210	0.034*
C9	0.1083 (3)	0.13129 (8)	0.39883 (12)	0.0259 (4)
H9	−0.0107	0.1550	0.4335	0.031*
C10	0.3260 (4)	0.11235 (9)	0.46255 (13)	0.0344 (5)
C11	0.4434 (5)	0.06056 (13)	0.59251 (17)	0.0572 (7)
H11A	0.3780	0.0341	0.6382	0.086*
H11B	0.5086	0.0978	0.6206	0.086*
H11C	0.5744	0.0393	0.5629	0.086*
C12	0.4564 (3)	0.19020 (8)	0.20530 (12)	0.0278 (4)
C13	0.6553 (3)	0.22127 (8)	0.24385 (14)	0.0314 (4)
H13	0.6881	0.2188	0.3065	0.038*
C14	0.8070 (4)	0.25591 (9)	0.19251 (17)	0.0410 (5)
H14	0.9427	0.2770	0.2195	0.049*
C15	0.7571 (4)	0.25908 (10)	0.10160 (17)	0.0455 (6)
H15	0.8616	0.2823	0.0660	0.055*
C16	0.5593 (4)	0.22943 (10)	0.06094 (15)	0.0418 (5)
H16	0.5270	0.2328	−0.0017	0.050*
C17	0.4075 (4)	0.19452 (8)	0.11258 (13)	0.0323 (4)
C18	0.1512 (5)	0.16733 (12)	−0.01499 (14)	0.0520 (6)
H18A	0.0059	0.1428	−0.0303	0.078*
H18B	0.2892	0.1523	−0.0479	0.078*
H18C	0.1187	0.2098	−0.0311	0.078*
C19	0.7699 (4)	−0.00092 (10)	0.06834 (13)	0.0351 (5)
H19A	0.8650	−0.0278	0.0311	0.053*
H19B	0.8806	0.0207	0.1108	0.053*
H19C	0.6803	0.0286	0.0303	0.053*
C20	0.0983 (4)	−0.13944 (9)	0.22980 (15)	0.0364 (5)
H20A	0.1191	−0.1815	0.2100	0.055*
H20B	−0.0640	−0.1248	0.2094	0.055*
H20C	0.1140	−0.1378	0.2951	0.055*

	U11	U22	U33	U12	U13	U23
O1	0.0496 (8)	0.0207 (7)	0.0370 (7)	−0.0003 (6)	0.0121 (6)	−0.0065 (6)
O2	0.0374 (7)	0.0271 (7)	0.0335 (7)	0.0029 (6)	0.0143 (6)	−0.0035 (5)
O3	0.0425 (8)	0.0194 (6)	0.0422 (8)	−0.0021 (6)	0.0122 (6)	−0.0042 (6)
O4	0.0335 (8)	0.0543 (10)	0.0441 (9)	0.0016 (7)	−0.0020 (6)	−0.0001 (7)
O5	0.0505 (10)	0.0559 (10)	0.0386 (8)	−0.0023 (8)	−0.0030 (7)	0.0157 (7)
O6	0.0542 (9)	0.0366 (8)	0.0261 (7)	0.0019 (7)	−0.0020 (6)	0.0010 (6)
N1	0.0295 (8)	0.0213 (7)	0.0247 (7)	−0.0006 (6)	0.0040 (6)	−0.0014 (6)
C1	0.0292 (9)	0.0223 (8)	0.0223 (8)	0.0019 (7)	0.0024 (7)	−0.0001 (7)
C2	0.0256 (9)	0.0225 (8)	0.0202 (8)	0.0007 (7)	0.0006 (6)	0.0006 (6)
C3	0.0279 (9)	0.0240 (9)	0.0225 (8)	−0.0005 (7)	0.0038 (7)	0.0002 (7)
C4	0.0275 (9)	0.0256 (9)	0.0211 (8)	0.0031 (7)	0.0034 (7)	−0.0019 (7)
C5	0.0315 (9)	0.0203 (8)	0.0261 (9)	0.0002 (7)	−0.0003 (7)	−0.0012 (7)
C6	0.0277 (9)	0.0250 (9)	0.0260 (9)	−0.0032 (7)	0.0033 (7)	0.0002 (7)
C7	0.0251 (8)	0.0240 (9)	0.0225 (8)	0.0010 (7)	0.0016 (6)	−0.0010 (7)
C8	0.0286 (9)	0.0269 (9)	0.0299 (9)	−0.0014 (7)	0.0071 (7)	−0.0023 (7)
C9	0.0304 (9)	0.0247 (9)	0.0230 (9)	0.0025 (7)	0.0074 (7)	0.0003 (7)
C10	0.0522 (13)	0.0269 (10)	0.0245 (9)	0.0061 (9)	0.0068 (8)	−0.0033 (7)
C11	0.0544 (15)	0.0673 (17)	0.0485 (14)	−0.0081 (13)	−0.0119 (11)	0.0216 (13)
C12	0.0350 (10)	0.0195 (8)	0.0294 (9)	0.0038 (7)	0.0081 (7)	0.0010 (7)
C13	0.0341 (10)	0.0227 (9)	0.0379 (10)	0.0024 (7)	0.0063 (8)	0.0016 (8)
C14	0.0370 (11)	0.0267 (10)	0.0603 (14)	−0.0005 (8)	0.0124 (10)	0.0053 (9)
C15	0.0492 (13)	0.0313 (11)	0.0583 (14)	0.0040 (9)	0.0258 (11)	0.0149 (10)
C16	0.0611 (14)	0.0319 (11)	0.0339 (11)	0.0092 (10)	0.0179 (10)	0.0106 (9)
C17	0.0436 (11)	0.0242 (9)	0.0296 (10)	0.0070 (8)	0.0071 (8)	0.0017 (7)
C18	0.0755 (17)	0.0523 (14)	0.0275 (11)	0.0137 (13)	−0.0059 (11)	−0.0040 (10)
C19	0.0360 (11)	0.0378 (11)	0.0325 (10)	0.0011 (8)	0.0132 (8)	−0.0016 (8)
C20	0.0423 (11)	0.0236 (9)	0.0438 (12)	−0.0061 (8)	0.0059 (9)	−0.0007 (8)

O1—N1	1.2995 (19)	C8—H8B	0.9900
O2—C4	1.366 (2)	C9—C10	1.549 (3)
O2—C19	1.429 (2)	C9—H9	1.0000
O3—C5	1.356 (2)	C11—H11A	0.9800
O3—C20	1.436 (2)	C11—H11B	0.9800
O4—C10	1.187 (3)	C11—H11C	0.9800
O5—C10	1.329 (3)	C12—C13	1.388 (3)
O5—C11	1.468 (3)	C12—C17	1.407 (3)
O6—C17	1.362 (3)	C13—C14	1.388 (3)
O6—C18	1.437 (2)	C13—H13	0.9500
N1—C1	1.320 (2)	C14—C15	1.380 (3)
N1—C9	1.476 (2)	C14—H14	0.9500
C1—C2	1.466 (2)	C15—C16	1.381 (4)
C1—C12	1.484 (2)	C15—H15	0.9500
C2—C7	1.393 (2)	C16—C17	1.394 (3)
C2—C3	1.408 (2)	C16—H16	0.9500
C3—C4	1.381 (2)	C18—H18A	0.9800
C3—H3	0.9500	C18—H18B	0.9800
C4—C5	1.411 (3)	C18—H18C	0.9800
C5—C6	1.386 (3)	C19—H19A	0.9800
C6—C7	1.394 (2)	C19—H19B	0.9800
C6—H6	0.9500	C19—H19C	0.9800
C7—C8	1.501 (2)	C20—H20A	0.9800
C8—C9	1.520 (2)	C20—H20B	0.9800
C8—H8A	0.9900	C20—H20C	0.9800
C4—O2—C19	117.10 (15)	O5—C11—H11A	109.5
C5—O3—C20	117.19 (15)	O5—C11—H11B	109.5
C10—O5—C11	112.08 (18)	H11A—C11—H11B	109.5
C17—O6—C18	117.57 (18)	O5—C11—H11C	109.5
O1—N1—C1	125.52 (15)	H11A—C11—H11C	109.5
O1—N1—C9	114.13 (14)	H11B—C11—H11C	109.5
C1—N1—C9	120.15 (15)	C13—C12—C17	119.13 (18)
N1—C1—C2	119.40 (16)	C13—C12—C1	119.27 (16)
N1—C1—C12	118.66 (15)	C17—C12—C1	121.42 (17)
C2—C1—C12	121.51 (15)	C12—C13—C14	121.2 (2)
C7—C2—C3	119.32 (16)	C12—C13—H13	119.4
C7—C2—C1	120.45 (16)	C14—C13—H13	119.4
C3—C2—C1	120.23 (16)	C15—C14—C13	118.7 (2)
C4—C3—C2	120.54 (16)	C15—C14—H14	120.6
C4—C3—H3	119.7	C13—C14—H14	120.6
C2—C3—H3	119.7	C14—C15—C16	121.8 (2)
O2—C4—C3	124.72 (16)	C14—C15—H15	119.1
O2—C4—C5	115.23 (15)	C16—C15—H15	119.1
C3—C4—C5	120.05 (16)	C15—C16—C17	119.4 (2)
O3—C5—C6	125.37 (16)	C15—C16—H16	120.3
O3—C5—C4	115.48 (16)	C17—C16—H16	120.3
C6—C5—C4	119.13 (16)	O6—C17—C16	124.20 (18)
C5—C6—C7	121.00 (16)	O6—C17—C12	116.05 (17)
C5—C6—H6	119.5	C16—C17—C12	119.8 (2)
C7—C6—H6	119.5	O6—C18—H18A	109.5
C2—C7—C6	119.92 (16)	O6—C18—H18B	109.5
C2—C7—C8	117.68 (15)	H18A—C18—H18B	109.5
C6—C7—C8	122.40 (16)	O6—C18—H18C	109.5
C7—C8—C9	110.07 (15)	H18A—C18—H18C	109.5
C7—C8—H8A	109.6	H18B—C18—H18C	109.5
C9—C8—H8A	109.6	O2—C19—H19A	109.5
C7—C8—H8B	109.6	O2—C19—H19B	109.5
C9—C8—H8B	109.6	H19A—C19—H19B	109.5
H8A—C8—H8B	108.2	O2—C19—H19C	109.5
N1—C9—C8	111.39 (14)	H19A—C19—H19C	109.5
N1—C9—C10	105.07 (14)	H19B—C19—H19C	109.5
C8—C9—C10	114.19 (15)	O3—C20—H20A	109.5
N1—C9—H9	108.7	O3—C20—H20B	109.5
C8—C9—H9	108.7	H20A—C20—H20B	109.5
C10—C9—H9	108.7	O3—C20—H20C	109.5
O4—C10—O5	124.7 (2)	H20A—C20—H20C	109.5
O4—C10—C9	125.50 (18)	H20B—C20—H20C	109.5
O5—C10—C9	109.75 (18)
O1—N1—C1—C2	177.89 (16)	O1—N1—C9—C8	146.52 (15)
C9—N1—C1—C2	3.4 (2)	C1—N1—C9—C8	−38.4 (2)
O1—N1—C1—C12	5.3 (3)	O1—N1—C9—C10	−89.34 (17)
C9—N1—C1—C12	−169.18 (15)	C1—N1—C9—C10	85.72 (18)
N1—C1—C2—C7	17.8 (2)	C7—C8—C9—N1	51.46 (19)
C12—C1—C2—C7	−169.84 (16)	C7—C8—C9—C10	−67.4 (2)
N1—C1—C2—C3	−161.82 (16)	C11—O5—C10—O4	3.0 (3)
C12—C1—C2—C3	10.6 (3)	C11—O5—C10—C9	−175.79 (18)
C7—C2—C3—C4	0.5 (3)	N1—C9—C10—O4	−0.3 (3)
C1—C2—C3—C4	−179.88 (16)	C8—C9—C10—O4	122.1 (2)
C19—O2—C4—C3	−2.9 (3)	N1—C9—C10—O5	178.51 (15)
C19—O2—C4—C5	176.99 (16)	C8—C9—C10—O5	−59.1 (2)
C2—C3—C4—O2	−178.80 (16)	N1—C1—C12—C13	56.9 (2)
C2—C3—C4—C5	1.3 (3)	C2—C1—C12—C13	−115.55 (19)
C20—O3—C5—C6	5.5 (3)	N1—C1—C12—C17	−128.06 (19)
C20—O3—C5—C4	−175.62 (16)	C2—C1—C12—C17	59.5 (2)
O2—C4—C5—O3	−1.0 (2)	C17—C12—C13—C14	−0.6 (3)
C3—C4—C5—O3	178.87 (16)	C1—C12—C13—C14	174.57 (17)
O2—C4—C5—C6	177.95 (15)	C12—C13—C14—C15	0.0 (3)
C3—C4—C5—C6	−2.2 (3)	C13—C14—C15—C16	0.8 (3)
O3—C5—C6—C7	−179.98 (17)	C14—C15—C16—C17	−1.0 (3)
C4—C5—C6—C7	1.2 (3)	C18—O6—C17—C16	−1.3 (3)
C3—C2—C7—C6	−1.5 (2)	C18—O6—C17—C12	178.88 (18)
C1—C2—C7—C6	178.87 (16)	C15—C16—C17—O6	−179.39 (19)
C3—C2—C7—C8	178.87 (15)	C15—C16—C17—C12	0.4 (3)
C1—C2—C7—C8	−0.7 (2)	C13—C12—C17—O6	−179.81 (16)
C5—C6—C7—C2	0.7 (3)	C1—C12—C17—O6	5.1 (3)
C5—C6—C7—C8	−179.74 (16)	C13—C12—C17—C16	0.4 (3)
C2—C7—C8—C9	−33.2 (2)	C1—C12—C17—C16	−174.66 (17)
C6—C7—C8—C9	147.19 (17)