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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010000353X/bk1516sup1.cif
Contains datablocks acta5, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010000353X/bk1516Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010000353X/bk1516IIsup3.hkl
Contains datablock II

CCDC references: 146064; 146065

Computing details top

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 top
Crystal data top
C11H12OS2F(000) = 236
Mr = 224.33Dx = 1.407 Mg m3
Triclinic, P1Melting point = 361.0–362.0 K
a = 6.6363 (13) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.1836 (16) ÅCell parameters from 2850 reflections
c = 10.468 (2) Åθ = 2.7–28.0°
α = 70.68 (3)°µ = 0.47 mm1
β = 88.01 (3)°T = 153 K
γ = 80.77 (3)°Block, colorless
V = 529.45 (18) Å30.46 × 0.37 × 0.30 mm
Z = 2
Data collection top
Bruker SMART1000 CCD
diffractometer
2363 independent reflections
Radiation source: standard-focus sealed tube2201 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ω scansθmax = 28.0°, θmin = 2.1°
Absorption correction: numerical
face indexed (SHELXTL/PC; Sheldrick, 1997)
h = 78
Tmin = 0.845, Tmax = 0.896k = 910
3410 measured reflectionsl = 1314
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 2.07 w = 1/[σ2(Fo2) + (0.04Fo2)2]
2363 reflections(Δ/σ)max = 0.001
127 parametersΔρmax = 0.66 e Å3
0 restraintsΔρmin = 0.31 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.56113 (6)0.65745 (5)0.29220 (4)0.03017 (15)
S20.97106 (6)0.77533 (5)0.20646 (4)0.02898 (15)
C10.7474 (2)0.85230 (18)0.40711 (14)0.0213 (3)
C20.7905 (2)0.70699 (19)0.52431 (15)0.0266 (3)
H2A0.80440.59240.51840.032*
C30.8134 (2)0.7274 (2)0.64948 (15)0.0303 (3)
H3A0.84260.62690.72810.036*
C40.7938 (2)0.8934 (2)0.66003 (15)0.0288 (3)
H4A0.80710.90730.74580.035*
C50.7548 (2)1.0390 (2)0.54463 (15)0.0256 (3)
H5A0.74251.15290.55180.031*
C60.73327 (19)1.02110 (18)0.41780 (14)0.0217 (3)
C70.6988 (2)1.18764 (19)0.30308 (15)0.0269 (3)
H7A0.68431.29180.32620.032*
C80.7198 (2)0.82571 (19)0.27297 (14)0.0239 (3)
H8A0.64850.93830.20850.029*
C90.5434 (3)0.6768 (2)0.11535 (17)0.0364 (4)
H9A0.45770.59220.10710.044*
H9B0.47310.79600.06450.044*
C100.7475 (3)0.6447 (2)0.04950 (17)0.0354 (4)
H10A0.72150.64620.04350.042*
H10B0.81910.52630.10110.042*
C110.8873 (3)0.7782 (2)0.04229 (16)0.0359 (4)
H11A0.81440.89690.00730.043*
H11B1.00900.75530.01030.043*
O10.68679 (18)1.20816 (14)0.18372 (11)0.0338 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0319 (2)0.0335 (3)0.0333 (3)0.01310 (17)0.00557 (16)0.01865 (18)
S20.0309 (2)0.0323 (3)0.0278 (2)0.01041 (17)0.00667 (16)0.01341 (17)
C10.0194 (6)0.0225 (7)0.0231 (7)0.0047 (5)0.0016 (5)0.0083 (5)
C20.0298 (7)0.0230 (7)0.0260 (7)0.0035 (6)0.0001 (6)0.0069 (6)
C30.0292 (7)0.0337 (8)0.0249 (8)0.0064 (6)0.0011 (6)0.0045 (6)
C40.0257 (7)0.0427 (9)0.0224 (7)0.0083 (6)0.0018 (5)0.0151 (6)
C50.0213 (6)0.0309 (8)0.0299 (8)0.0061 (6)0.0042 (5)0.0164 (6)
C60.0183 (6)0.0236 (7)0.0247 (7)0.0051 (5)0.0029 (5)0.0095 (5)
C70.0272 (7)0.0208 (7)0.0337 (8)0.0050 (6)0.0014 (6)0.0100 (6)
C80.0275 (7)0.0212 (7)0.0249 (7)0.0037 (5)0.0000 (5)0.0100 (5)
C90.0433 (9)0.0377 (9)0.0351 (9)0.0112 (7)0.0049 (7)0.0185 (7)
C100.0546 (10)0.0322 (9)0.0254 (8)0.0142 (7)0.0054 (7)0.0147 (7)
C110.0551 (10)0.0337 (9)0.0242 (8)0.0169 (8)0.0099 (7)0.0128 (6)
O10.0461 (7)0.0258 (6)0.0278 (6)0.0078 (5)0.0015 (5)0.0052 (4)
Geometric parameters (Å, º) top
S1—C81.8198 (15)C2—C31.3906 (19)
S2—C81.8233 (15)C3—C41.385 (2)
S1—C91.8113 (17)C4—C51.384 (2)
S2—C111.8161 (16)C5—C61.3973 (19)
C9—C101.523 (3)C1—C61.4105 (19)
C10—C111.525 (2)C6—C71.479 (2)
C1—C81.5118 (19)C7—O11.2080 (18)
C1—C21.397 (2)
C9—S1—C897.89 (8)C5—C6—C7115.14 (12)
C11—S2—C897.73 (8)C1—C6—C7125.22 (13)
C2—C1—C8119.79 (13)O1—C7—C6128.29 (13)
C6—C1—C8121.80 (13)C1—C8—S1110.48 (10)
C1—C2—C3121.09 (14)C1—C8—S2108.61 (10)
C2—C3—C4120.27 (15)S1—C8—S2113.06 (8)
C3—C4—C5119.45 (14)C10—C9—S1114.74 (12)
C4—C5—C6121.09 (14)C9—C10—C11114.16 (14)
C5—C6—C1119.64 (13)C10—C11—S2114.07 (12)
C6—C1—C2118.41 (13)
C8—C1—C9—C1041.9 (2)C10—C11—S2—C859.84 (14)
C1—C9—C10—C1136.58 (15)C6—C1—C7—O1177.00 (19)
C9—C10—C11—S264.50 (18)C2—C1—C7—O1172.00 (18)
(II) N-{2-[2-(1,3-dioxan-2-yl)phenoxy]ethyl}phthalimide top
Crystal data top
C20H19NO5Dx = 1.373 Mg m3
Mr = 353.36Melting point = 438.0–439.0 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.0200 (4) ÅCell parameters from 2806 reflections
b = 15.0289 (11) Åθ = 2.6–27.7°
c = 18.9660 (13) ŵ = 0.10 mm1
β = 94.841 (1)°T = 153 K
V = 1709.8 (2) Å3Square prism, colorless
Z = 40.47 × 0.12 × 0.06 mm
F(000) = 744
Data collection top
Bruker SMART1000 CCD
diffractometer
4034 independent reflections
Radiation source: standard-focus sealed tube2314 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω scansθmax = 28.0°, θmin = 1.7°
Absorption correction: numerical
face indexed (SHELXTL/PC; Sheldrick, 1997)
h = 78
Tmin = 0.967, Tmax = 0.994k = 1918
11075 measured reflectionsl = 2424
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.03Fo2)2]
4034 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.20 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.7568 (2)0.45358 (8)0.41882 (6)0.0399 (3)
O20.7630 (2)0.16188 (8)0.35072 (6)0.0394 (3)
O30.7351 (2)0.32218 (8)0.22657 (6)0.0348 (3)
O40.2952 (2)0.16051 (8)0.11862 (6)0.0348 (3)
O50.2658 (2)0.20866 (8)0.23409 (6)0.0392 (3)
N10.8019 (2)0.31271 (9)0.37402 (7)0.0285 (4)
C10.5203 (3)0.24150 (11)0.42539 (9)0.0287 (4)
C20.3674 (3)0.18090 (12)0.44695 (9)0.0345 (5)
H2A0.36850.12060.43210.041*
C30.2122 (3)0.21156 (13)0.49114 (9)0.0372 (5)
H3A0.10460.17160.50690.045*
C40.2112 (3)0.29962 (13)0.51272 (9)0.0362 (5)
H4A0.10270.31890.54300.043*
C50.3658 (3)0.36030 (12)0.49103 (9)0.0340 (5)
H5A0.36560.42070.50590.041*
C60.5191 (3)0.32924 (11)0.44709 (8)0.0285 (4)
C70.7024 (3)0.37625 (12)0.41415 (9)0.0295 (4)
C80.7039 (3)0.22888 (12)0.37882 (9)0.0305 (4)
C90.9817 (3)0.33180 (12)0.32972 (9)0.0299 (4)
H9A1.05430.27540.31750.036*
H9B1.09500.36930.35640.036*
C100.8979 (3)0.37913 (12)0.26276 (9)0.0312 (4)
H10A0.82990.43680.27400.037*
H10B1.02210.39040.23290.037*
C110.5914 (3)0.35914 (11)0.17536 (9)0.0277 (4)
C120.6159 (3)0.44371 (11)0.14827 (9)0.0330 (5)
H12A0.74090.47920.16410.040*
C130.4568 (3)0.47615 (12)0.09787 (9)0.0365 (5)
H13A0.47310.53420.07920.044*
C140.2748 (3)0.42521 (12)0.07447 (10)0.0385 (5)
H14A0.16420.44850.04070.046*
C150.2547 (3)0.33986 (12)0.10064 (9)0.0339 (5)
H15A0.13030.30450.08400.041*
C160.4122 (3)0.30507 (11)0.15055 (9)0.0270 (4)
C170.3953 (3)0.21089 (11)0.17533 (8)0.0275 (4)
H17A0.54780.18710.18940.033*
C180.2757 (3)0.06888 (11)0.13742 (9)0.0380 (5)
H18A0.42590.04320.14880.046*
H18B0.20200.03540.09700.046*
C190.1412 (3)0.06063 (12)0.20039 (10)0.0413 (5)
H19A0.14030.00200.21640.050*
H19B0.01470.07910.18730.050*
C200.2431 (4)0.11902 (13)0.25902 (9)0.0430 (5)
H20A0.14760.11860.29900.052*
H20B0.39150.09550.27620.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0458 (9)0.0267 (8)0.0481 (8)0.0038 (6)0.0096 (7)0.0066 (6)
O20.0432 (9)0.0285 (8)0.0470 (8)0.0037 (6)0.0061 (7)0.0075 (6)
O30.0365 (8)0.0290 (7)0.0369 (7)0.0060 (6)0.0082 (6)0.0016 (6)
O40.0463 (8)0.0273 (7)0.0301 (7)0.0054 (6)0.0014 (6)0.0025 (6)
O50.0546 (9)0.0295 (8)0.0359 (7)0.0003 (6)0.0180 (7)0.0009 (6)
N10.0294 (9)0.0260 (9)0.0299 (8)0.0018 (7)0.0011 (7)0.0028 (7)
C10.0305 (11)0.0294 (11)0.0256 (9)0.0004 (8)0.0016 (9)0.0013 (8)
C20.0411 (12)0.0313 (11)0.0300 (10)0.0032 (9)0.0032 (9)0.0018 (8)
C30.0375 (12)0.0436 (13)0.0301 (10)0.0059 (9)0.0004 (10)0.0059 (9)
C40.0360 (12)0.0460 (13)0.0266 (10)0.0014 (10)0.0035 (9)0.0014 (9)
C50.0391 (12)0.0370 (12)0.0257 (10)0.0041 (9)0.0006 (9)0.0013 (8)
C60.0304 (11)0.0295 (10)0.0245 (9)0.0009 (8)0.0031 (8)0.0003 (8)
C70.0302 (11)0.0289 (11)0.0289 (10)0.0029 (9)0.0013 (9)0.0017 (8)
C80.0328 (11)0.0275 (11)0.0303 (10)0.0026 (8)0.0031 (9)0.0001 (8)
C90.0258 (10)0.0324 (11)0.0312 (10)0.0004 (8)0.0013 (8)0.0018 (8)
C100.0313 (11)0.0299 (11)0.0320 (10)0.0031 (8)0.0004 (9)0.0037 (8)
C110.0281 (11)0.0306 (11)0.0243 (9)0.0037 (8)0.0017 (8)0.0012 (8)
C120.0374 (12)0.0281 (11)0.0333 (10)0.0009 (9)0.0019 (9)0.0019 (9)
C130.0494 (13)0.0239 (10)0.0363 (11)0.0060 (9)0.0034 (10)0.0011 (8)
C140.0421 (13)0.0324 (12)0.0391 (11)0.0074 (9)0.0074 (10)0.0013 (9)
C150.0324 (11)0.0332 (11)0.0354 (11)0.0026 (9)0.0010 (9)0.0018 (9)
C160.0298 (11)0.0278 (10)0.0237 (9)0.0034 (8)0.0032 (9)0.0024 (8)
C170.0250 (10)0.0289 (10)0.0284 (10)0.0016 (8)0.0010 (9)0.0031 (8)
C180.0465 (13)0.0261 (11)0.0408 (11)0.0043 (9)0.0006 (10)0.0032 (9)
C190.0382 (12)0.0299 (11)0.0563 (13)0.0042 (9)0.0071 (11)0.0043 (10)
C200.0586 (15)0.0323 (12)0.0404 (12)0.0021 (10)0.0176 (11)0.0033 (9)
Geometric parameters (Å, º) top
O1—C71.209 (2)C18—C191.503 (2)
O2—C81.2070 (19)C19—C201.506 (3)
N1—C71.388 (2)O5—C201.438 (2)
C6—C71.491 (2)O5—C171.4132 (19)
C1—C61.382 (2)C1—C21.381 (2)
C1—C81.484 (2)C2—C31.386 (2)
N1—C81.397 (2)C3—C41.385 (3)
N1—C91.454 (2)C4—C51.390 (2)
C9—C101.505 (2)C5—C61.376 (2)
O3—C101.432 (2)C11—C121.384 (2)
O3—C111.3632 (19)C12—C131.384 (2)
C11—C161.400 (2)C13—C141.379 (3)
C16—C171.498 (2)C14—C151.384 (2)
O4—C171.4085 (19)C15—C161.385 (2)
O4—C181.4297 (19)
C11—O3—C10117.74 (14)N1—C9—C10111.57 (14)
C7—N1—C9123.90 (15)O3—C10—C9106.81 (14)
C8—N1—C9123.69 (14)O3—C11—C12123.90 (17)
C2—C1—C8129.82 (17)O3—C11—C16115.33 (16)
C1—C2—C3117.40 (17)C12—C11—C16120.78 (17)
C2—C3—C4121.07 (18)C11—C12—C13119.39 (18)
C3—C4—C5121.32 (18)C14—C13—C12120.78 (18)
C4—C5—C6117.18 (18)C13—C14—C15119.36 (18)
C5—C6—C1121.64 (17)C14—C15—C16121.28 (18)
C6—C1—C2121.39 (17)C15—C16—C11118.34 (17)
C5—C6—C7130.61 (16)C15—C16—C17120.71 (16)
C1—C6—C7107.74 (15)C11—C16—C17120.92 (16)
N1—C7—C6105.81 (15)O4—C17—O5111.13 (14)
C7—N1—C8112.37 (15)O4—C17—C16107.72 (14)
N1—C8—C1105.26 (15)O5—C17—C16109.06 (14)
C6—C1—C8108.79 (15)C17—O4—C18111.48 (13)
O1—C7—N1125.12 (17)O4—C18—C19109.80 (15)
O1—C7—C6129.06 (16)C18—C19—C20108.99 (16)
O2—C8—N1125.56 (17)O5—C20—C19110.32 (15)
O2—C8—C1129.18 (17)C17—O5—C20110.82 (13)
C7—N1—C9—C1075.2 (2)C17—O4—C18—C1958.16 (19)
N1—C9—C10—O358.87 (18)O4—C18—C19—C2053.9 (2)
C9—C10—O3—C11162.18 (14)C18—C19—C20—O553.8 (2)
C10—O3—C11—C16169.17 (15)C19—C20—O5—C1757.2 (2)
 

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