2-(1,3-Dithian-2-yl)benzaldehyde and N-{2-[2-(1,3-dioxan-2-yl)phenoxy]­ethyl}phthalimide

The crystal structures of two elaborated-porphyrin precursors have been determined. In the crystalline state, 2-(1,3-di­thian-2-yl)­benz­aldehyde, C₁₁H₁₂OS₂, has its di­thiane ring in a slightly distorted chair conformation. The mol­ecules pack in anti-parallel chains. N-{2-[2-(1,3-Dioxan-2-yl)­phenoxy]­ethyl}­phthal­imide, C₂₀H₁₉NO₅, is in a folded conformation. The dihedral angle between the phthal­imide and phenyl planes is 80.07 (3)°. In the crystalline states, mol­ecules stack on top of one another.

Computing details

For both compounds, data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 1997); molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

(I) 2-(1,3-dithian-2-yl)benzaldehyde

Crystal data

C11H12OS2	F(000) = 236
Mr = 224.33	Dx = 1.407 Mg m^−3
Triclinic, P1	Melting point = 361.0–362.0 K
a = 6.6363 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1836 (16) Å	Cell parameters from 2850 reflections
c = 10.468 (2) Å	θ = 2.7–28.0°
α = 70.68 (3)°	µ = 0.47 mm^−1
β = 88.01 (3)°	T = 153 K
γ = 80.77 (3)°	Block, colorless
V = 529.45 (18) Å^3	0.46 × 0.37 × 0.30 mm
Z = 2

Data collection

Bruker SMART1000 CCD diffractometer	2363 independent reflections
Radiation source: standard-focus sealed tube	2201 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
ω scans	θmax = 28.0°, θmin = 2.1°
Absorption correction: numerical face indexed (SHELXTL/PC; Sheldrick, 1997)	h = −7→8
Tmin = 0.845, Tmax = 0.896	k = −9→10
3410 measured reflections	l = −13→14

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 2.07	w = 1/[σ^2(Fo^2) + (0.04Fo^2)^2]
2363 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.66 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

Experimental. For both compounds, the crystal to detector distance was 5.023 cm. Each frame covered -0.3° in ω for 5 s. Data were collected at 153 K in groups of 606, 435, and 230 frames at φ settings of 0°, 90°, and 180°, respectively. Crystals were attached to glass fibers with a minimum of silicone cement.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.56113 (6)	0.65745 (5)	0.29220 (4)	0.03017 (15)
S2	0.97106 (6)	0.77533 (5)	0.20646 (4)	0.02898 (15)
C1	0.7474 (2)	0.85230 (18)	0.40711 (14)	0.0213 (3)
C2	0.7905 (2)	0.70699 (19)	0.52431 (15)	0.0266 (3)
H2A	0.8044	0.5924	0.5184	0.032*
C3	0.8134 (2)	0.7274 (2)	0.64948 (15)	0.0303 (3)
H3A	0.8426	0.6269	0.7281	0.036*
C4	0.7938 (2)	0.8934 (2)	0.66003 (15)	0.0288 (3)
H4A	0.8071	0.9073	0.7458	0.035*
C5	0.7548 (2)	1.0390 (2)	0.54463 (15)	0.0256 (3)
H5A	0.7425	1.1529	0.5518	0.031*
C6	0.73327 (19)	1.02110 (18)	0.41780 (14)	0.0217 (3)
C7	0.6988 (2)	1.18764 (19)	0.30308 (15)	0.0269 (3)
H7A	0.6843	1.2918	0.3262	0.032*
C8	0.7198 (2)	0.82571 (19)	0.27297 (14)	0.0239 (3)
H8A	0.6485	0.9383	0.2085	0.029*
C9	0.5434 (3)	0.6768 (2)	0.11535 (17)	0.0364 (4)
H9A	0.4577	0.5922	0.1071	0.044*
H9B	0.4731	0.7960	0.0645	0.044*
C10	0.7475 (3)	0.6447 (2)	0.04950 (17)	0.0354 (4)
H10A	0.7215	0.6462	−0.0435	0.042*
H10B	0.8191	0.5263	0.1011	0.042*
C11	0.8873 (3)	0.7782 (2)	0.04229 (16)	0.0359 (4)
H11A	0.8144	0.8969	−0.0073	0.043*
H11B	1.0090	0.7553	−0.0103	0.043*
O1	0.68679 (18)	1.20816 (14)	0.18372 (11)	0.0338 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0319 (2)	0.0335 (3)	0.0333 (3)	−0.01310 (17)	0.00557 (16)	−0.01865 (18)
S2	0.0309 (2)	0.0323 (3)	0.0278 (2)	−0.01041 (17)	0.00667 (16)	−0.01341 (17)
C1	0.0194 (6)	0.0225 (7)	0.0231 (7)	−0.0047 (5)	0.0016 (5)	−0.0083 (5)
C2	0.0298 (7)	0.0230 (7)	0.0260 (7)	−0.0035 (6)	−0.0001 (6)	−0.0069 (6)
C3	0.0292 (7)	0.0337 (8)	0.0249 (8)	−0.0064 (6)	−0.0011 (6)	−0.0045 (6)
C4	0.0257 (7)	0.0427 (9)	0.0224 (7)	−0.0083 (6)	0.0018 (5)	−0.0151 (6)
C5	0.0213 (6)	0.0309 (8)	0.0299 (8)	−0.0061 (6)	0.0042 (5)	−0.0164 (6)
C6	0.0183 (6)	0.0236 (7)	0.0247 (7)	−0.0051 (5)	0.0029 (5)	−0.0095 (5)
C7	0.0272 (7)	0.0208 (7)	0.0337 (8)	−0.0050 (6)	0.0014 (6)	−0.0100 (6)
C8	0.0275 (7)	0.0212 (7)	0.0249 (7)	−0.0037 (5)	0.0000 (5)	−0.0100 (5)
C9	0.0433 (9)	0.0377 (9)	0.0351 (9)	−0.0112 (7)	−0.0049 (7)	−0.0185 (7)
C10	0.0546 (10)	0.0322 (9)	0.0254 (8)	−0.0142 (7)	0.0054 (7)	−0.0147 (7)
C11	0.0551 (10)	0.0337 (9)	0.0242 (8)	−0.0169 (8)	0.0099 (7)	−0.0128 (6)
O1	0.0461 (7)	0.0258 (6)	0.0278 (6)	−0.0078 (5)	−0.0015 (5)	−0.0052 (4)

Geometric parameters (Å, º)

S1—C8	1.8198 (15)	C2—C3	1.3906 (19)
S2—C8	1.8233 (15)	C3—C4	1.385 (2)
S1—C9	1.8113 (17)	C4—C5	1.384 (2)
S2—C11	1.8161 (16)	C5—C6	1.3973 (19)
C9—C10	1.523 (3)	C1—C6	1.4105 (19)
C10—C11	1.525 (2)	C6—C7	1.479 (2)
C1—C8	1.5118 (19)	C7—O1	1.2080 (18)
C1—C2	1.397 (2)
C9—S1—C8	97.89 (8)	C5—C6—C7	115.14 (12)
C11—S2—C8	97.73 (8)	C1—C6—C7	125.22 (13)
C2—C1—C8	119.79 (13)	O1—C7—C6	128.29 (13)
C6—C1—C8	121.80 (13)	C1—C8—S1	110.48 (10)
C1—C2—C3	121.09 (14)	C1—C8—S2	108.61 (10)
C2—C3—C4	120.27 (15)	S1—C8—S2	113.06 (8)
C3—C4—C5	119.45 (14)	C10—C9—S1	114.74 (12)
C4—C5—C6	121.09 (14)	C9—C10—C11	114.16 (14)
C5—C6—C1	119.64 (13)	C10—C11—S2	114.07 (12)
C6—C1—C2	118.41 (13)
C8—C1—C9—C10	41.9 (2)	C10—C11—S2—C8	−59.84 (14)
C1—C9—C10—C11	−36.58 (15)	C6—C1—C7—O1	177.00 (19)
C9—C10—C11—S2	64.50 (18)	C2—C1—C7—O1	172.00 (18)

(II) N-{2-[2-(1,3-dioxan-2-yl)phenoxy]ethyl}phthalimide

Crystal data

C20H19NO5	Dx = 1.373 Mg m^−3
Mr = 353.36	Melting point = 438.0–439.0 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.0200 (4) Å	Cell parameters from 2806 reflections
b = 15.0289 (11) Å	θ = 2.6–27.7°
c = 18.9660 (13) Å	µ = 0.10 mm^−1
β = 94.841 (1)°	T = 153 K
V = 1709.8 (2) Å^3	Square prism, colorless
Z = 4	0.47 × 0.12 × 0.06 mm
F(000) = 744

Data collection

Bruker SMART1000 CCD diffractometer	4034 independent reflections
Radiation source: standard-focus sealed tube	2314 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω scans	θmax = 28.0°, θmin = 1.7°
Absorption correction: numerical face indexed (SHELXTL/PC; Sheldrick, 1997)	h = −7→8
Tmin = 0.967, Tmax = 0.994	k = −19→18
11075 measured reflections	l = −24→24

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.03Fo^2)^2]
4034 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Experimental. For both compounds, the crystal to detector distance was 5.023 cm. Each frame covered -0.3° in ω for 5 s. Data were collected at 153 K in groups of 606, 435, and 230 frames at φ settings of 0°, 90°, and 180°, respectively. Crystals were attached to glass fibers with a minimum of silicone cement.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.7568 (2)	0.45358 (8)	0.41882 (6)	0.0399 (3)
O2	0.7630 (2)	0.16188 (8)	0.35072 (6)	0.0394 (3)
O3	0.7351 (2)	0.32218 (8)	0.22657 (6)	0.0348 (3)
O4	0.2952 (2)	0.16051 (8)	0.11862 (6)	0.0348 (3)
O5	0.2658 (2)	0.20866 (8)	0.23409 (6)	0.0392 (3)
N1	0.8019 (2)	0.31271 (9)	0.37402 (7)	0.0285 (4)
C1	0.5203 (3)	0.24150 (11)	0.42539 (9)	0.0287 (4)
C2	0.3674 (3)	0.18090 (12)	0.44695 (9)	0.0345 (5)
H2A	0.3685	0.1206	0.4321	0.041*
C3	0.2122 (3)	0.21156 (13)	0.49114 (9)	0.0372 (5)
H3A	0.1046	0.1716	0.5069	0.045*
C4	0.2112 (3)	0.29962 (13)	0.51272 (9)	0.0362 (5)
H4A	0.1027	0.3189	0.5430	0.043*
C5	0.3658 (3)	0.36030 (12)	0.49103 (9)	0.0340 (5)
H5A	0.3656	0.4207	0.5059	0.041*
C6	0.5191 (3)	0.32924 (11)	0.44709 (8)	0.0285 (4)
C7	0.7024 (3)	0.37625 (12)	0.41415 (9)	0.0295 (4)
C8	0.7039 (3)	0.22888 (12)	0.37882 (9)	0.0305 (4)
C9	0.9817 (3)	0.33180 (12)	0.32972 (9)	0.0299 (4)
H9A	1.0543	0.2754	0.3175	0.036*
H9B	1.0950	0.3693	0.3564	0.036*
C10	0.8979 (3)	0.37913 (12)	0.26276 (9)	0.0312 (4)
H10A	0.8299	0.4368	0.2740	0.037*
H10B	1.0221	0.3904	0.2329	0.037*
C11	0.5914 (3)	0.35914 (11)	0.17536 (9)	0.0277 (4)
C12	0.6159 (3)	0.44371 (11)	0.14827 (9)	0.0330 (5)
H12A	0.7409	0.4792	0.1641	0.040*
C13	0.4568 (3)	0.47615 (12)	0.09787 (9)	0.0365 (5)
H13A	0.4731	0.5342	0.0792	0.044*
C14	0.2748 (3)	0.42521 (12)	0.07447 (10)	0.0385 (5)
H14A	0.1642	0.4485	0.0407	0.046*
C15	0.2547 (3)	0.33986 (12)	0.10064 (9)	0.0339 (5)
H15A	0.1303	0.3045	0.0840	0.041*
C16	0.4122 (3)	0.30507 (11)	0.15055 (9)	0.0270 (4)
C17	0.3953 (3)	0.21089 (11)	0.17533 (8)	0.0275 (4)
H17A	0.5478	0.1871	0.1894	0.033*
C18	0.2757 (3)	0.06888 (11)	0.13742 (9)	0.0380 (5)
H18A	0.4259	0.0432	0.1488	0.046*
H18B	0.2020	0.0354	0.0970	0.046*
C19	0.1412 (3)	0.06063 (12)	0.20039 (10)	0.0413 (5)
H19A	0.1403	−0.0020	0.2164	0.050*
H19B	−0.0147	0.0791	0.1873	0.050*
C20	0.2431 (4)	0.11902 (13)	0.25902 (9)	0.0430 (5)
H20A	0.1476	0.1186	0.2990	0.052*
H20B	0.3915	0.0955	0.2762	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0458 (9)	0.0267 (8)	0.0481 (8)	−0.0038 (6)	0.0096 (7)	−0.0066 (6)
O2	0.0432 (9)	0.0285 (8)	0.0470 (8)	0.0037 (6)	0.0061 (7)	−0.0075 (6)
O3	0.0365 (8)	0.0290 (7)	0.0369 (7)	−0.0060 (6)	−0.0082 (6)	0.0016 (6)
O4	0.0463 (8)	0.0273 (7)	0.0301 (7)	−0.0054 (6)	−0.0014 (6)	−0.0025 (6)
O5	0.0546 (9)	0.0295 (8)	0.0359 (7)	−0.0003 (6)	0.0180 (7)	0.0009 (6)
N1	0.0294 (9)	0.0260 (9)	0.0299 (8)	0.0018 (7)	0.0011 (7)	−0.0028 (7)
C1	0.0305 (11)	0.0294 (11)	0.0256 (9)	−0.0004 (8)	−0.0016 (9)	0.0013 (8)
C2	0.0411 (12)	0.0313 (11)	0.0300 (10)	−0.0032 (9)	−0.0032 (9)	0.0018 (8)
C3	0.0375 (12)	0.0436 (13)	0.0301 (10)	−0.0059 (9)	0.0004 (10)	0.0059 (9)
C4	0.0360 (12)	0.0460 (13)	0.0266 (10)	0.0014 (10)	0.0035 (9)	0.0014 (9)
C5	0.0391 (12)	0.0370 (12)	0.0257 (10)	0.0041 (9)	0.0006 (9)	−0.0013 (8)
C6	0.0304 (11)	0.0295 (10)	0.0245 (9)	0.0009 (8)	−0.0031 (8)	0.0003 (8)
C7	0.0302 (11)	0.0289 (11)	0.0289 (10)	0.0029 (9)	−0.0013 (9)	−0.0017 (8)
C8	0.0328 (11)	0.0275 (11)	0.0303 (10)	0.0026 (8)	−0.0031 (9)	0.0001 (8)
C9	0.0258 (10)	0.0324 (11)	0.0312 (10)	0.0004 (8)	0.0013 (8)	−0.0018 (8)
C10	0.0313 (11)	0.0299 (11)	0.0320 (10)	−0.0031 (8)	0.0004 (9)	−0.0037 (8)
C11	0.0281 (11)	0.0306 (11)	0.0243 (9)	0.0037 (8)	0.0017 (8)	−0.0012 (8)
C12	0.0374 (12)	0.0281 (11)	0.0333 (10)	−0.0009 (9)	0.0019 (9)	−0.0019 (9)
C13	0.0494 (13)	0.0239 (10)	0.0363 (11)	0.0060 (9)	0.0034 (10)	0.0011 (8)
C14	0.0421 (13)	0.0324 (12)	0.0391 (11)	0.0074 (9)	−0.0074 (10)	0.0013 (9)
C15	0.0324 (11)	0.0332 (11)	0.0354 (11)	0.0026 (9)	−0.0010 (9)	−0.0018 (9)
C16	0.0298 (11)	0.0278 (10)	0.0237 (9)	0.0034 (8)	0.0032 (9)	−0.0024 (8)
C17	0.0250 (10)	0.0289 (10)	0.0284 (10)	−0.0016 (8)	0.0010 (9)	−0.0031 (8)
C18	0.0465 (13)	0.0261 (11)	0.0408 (11)	−0.0043 (9)	−0.0006 (10)	−0.0032 (9)
C19	0.0382 (12)	0.0299 (11)	0.0563 (13)	−0.0042 (9)	0.0071 (11)	0.0043 (10)
C20	0.0586 (15)	0.0323 (12)	0.0404 (12)	−0.0021 (10)	0.0176 (11)	0.0033 (9)

Geometric parameters (Å, º)

O1—C7	1.209 (2)	C18—C19	1.503 (2)
O2—C8	1.2070 (19)	C19—C20	1.506 (3)
N1—C7	1.388 (2)	O5—C20	1.438 (2)
C6—C7	1.491 (2)	O5—C17	1.4132 (19)
C1—C6	1.382 (2)	C1—C2	1.381 (2)
C1—C8	1.484 (2)	C2—C3	1.386 (2)
N1—C8	1.397 (2)	C3—C4	1.385 (3)
N1—C9	1.454 (2)	C4—C5	1.390 (2)
C9—C10	1.505 (2)	C5—C6	1.376 (2)
O3—C10	1.432 (2)	C11—C12	1.384 (2)
O3—C11	1.3632 (19)	C12—C13	1.384 (2)
C11—C16	1.400 (2)	C13—C14	1.379 (3)
C16—C17	1.498 (2)	C14—C15	1.384 (2)
O4—C17	1.4085 (19)	C15—C16	1.385 (2)
O4—C18	1.4297 (19)
C11—O3—C10	117.74 (14)	N1—C9—C10	111.57 (14)
C7—N1—C9	123.90 (15)	O3—C10—C9	106.81 (14)
C8—N1—C9	123.69 (14)	O3—C11—C12	123.90 (17)
C2—C1—C8	129.82 (17)	O3—C11—C16	115.33 (16)
C1—C2—C3	117.40 (17)	C12—C11—C16	120.78 (17)
C2—C3—C4	121.07 (18)	C11—C12—C13	119.39 (18)
C3—C4—C5	121.32 (18)	C14—C13—C12	120.78 (18)
C4—C5—C6	117.18 (18)	C13—C14—C15	119.36 (18)
C5—C6—C1	121.64 (17)	C14—C15—C16	121.28 (18)
C6—C1—C2	121.39 (17)	C15—C16—C11	118.34 (17)
C5—C6—C7	130.61 (16)	C15—C16—C17	120.71 (16)
C1—C6—C7	107.74 (15)	C11—C16—C17	120.92 (16)
N1—C7—C6	105.81 (15)	O4—C17—O5	111.13 (14)
C7—N1—C8	112.37 (15)	O4—C17—C16	107.72 (14)
N1—C8—C1	105.26 (15)	O5—C17—C16	109.06 (14)
C6—C1—C8	108.79 (15)	C17—O4—C18	111.48 (13)
O1—C7—N1	125.12 (17)	O4—C18—C19	109.80 (15)
O1—C7—C6	129.06 (16)	C18—C19—C20	108.99 (16)
O2—C8—N1	125.56 (17)	O5—C20—C19	110.32 (15)
O2—C8—C1	129.18 (17)	C17—O5—C20	110.82 (13)
C7—N1—C9—C10	−75.2 (2)	C17—O4—C18—C19	58.16 (19)
N1—C9—C10—O3	−58.87 (18)	O4—C18—C19—C20	−53.9 (2)
C9—C10—O3—C11	162.18 (14)	C18—C19—C20—O5	53.8 (2)
C10—O3—C11—C16	−169.17 (15)	C19—C20—O5—C17	−57.2 (2)