Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031820/rk2022sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031820/rk2022Isup2.hkl |
CCDC reference: 658979
Crystals were handled as described by Hope (1994). The compound was prepared as described by Terry et al. (1965) and Kenner et al. (1977) and was crystallized from CH2Cl2/n-hexane.
H atoms were mostly placed in geometrically idealized positions and constrained to ride on their parent atoms with C–H distances in the range of 0.95–1.00 Å and Uiso (H) = 1.2 Ueq (C) for CH– and CH2-groups and Uiso (H) = 1.5 Ueq (C) for methyl groups. The pyrrole hydrogen atom was refined with isotropic thermal parameters.
In continuation of studies on the hydrogen bonding pattern in pyrroles (Senge & Smith, 2005), dipyrromethanes (Senge, 2005) and porphyrins (Senge, 2000) the title compound was investigated for N–H···O and C–H···O interactions using the criteria put forward by Steiner (1997).
The structure is characterized by an intramolecular hydrogen bond between the pyrrole hydrogen and O1 from the phthalimido group [N1–H1···O1, 2.506 (17) Å, 119.1 (15)°]. The pyrrole hydrogen atom is also involved in intermolecular hydrogen bond, which is formed with the carbonyl oxygen atom (O2) of the phthalimido group not involved in the intramolecular hydrogen bond [N1–H1···O2, 2.520 (19) Å, 137.8 (15)°]. As indicated by their bond lenghts, both hydrogen bonds are relatively weak. The phthalimido group also participates in C–H···O interactions. Atom O1 is in close contact with an aromatic C–H unit [C27–H27···O1 = 2.30 (2) Å], while O2 is in close contact to an aliphatic CH2-group [C52–H52···O2 = 2.40 (2) Å]. The benzylic ester group is only involved in a contact to another aromatic C–H unit [C24–H24···O3 = 2.48 (2) Å]. Thus, arrangement of the molecules in the crystal is dominated by intermolecular contacts involving the phthalimido groups. These arrange in parallel layers with the benzylester groups forming an outer rim of this ladder-type arrangement.
For related literature, see: Senge (2000, 2005); Senge & Smith (2005). The compound was prepared as described by Terry et al. (1965) and Kenner et al. (1977); crystals were handled as described by Hope (1994). The hydrogen-bonding analysis followed the criteria set out by Steiner (1997).
Data collection: P3/PC (Siemens, 1995a); cell refinement: P3/PC; data reduction: XDISK (Siemens, 1995b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1995b); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C24H22N2O4 | F(000) = 848 |
Mr = 402.44 | Dx = 1.325 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 33 reflections |
a = 19.322 (6) Å | θ = 19–23° |
b = 7.482 (4) Å | µ = 0.09 mm−1 |
c = 14.104 (3) Å | T = 130 K |
β = 98.27 (2)° | Block, colorless |
V = 2017.8 (13) Å3 | 0.50 × 0.44 × 0.40 mm |
Z = 4 |
Siemens R3m/V diffractometer | Rint = 0.037 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 2.1° |
Graphite monochromator | h = −25→24 |
ω scans | k = 0→9 |
5193 measured reflections | l = 0→18 |
4631 independent reflections | 2 standard reflections every 198 reflections |
3592 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0622P)2 + 0.3895P] where P = (Fo2 + 2Fc2)/3 |
4631 reflections | (Δ/σ)max = 0.002 |
277 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C24H22N2O4 | V = 2017.8 (13) Å3 |
Mr = 402.44 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 19.322 (6) Å | µ = 0.09 mm−1 |
b = 7.482 (4) Å | T = 130 K |
c = 14.104 (3) Å | 0.50 × 0.44 × 0.40 mm |
β = 98.27 (2)° |
Siemens R3m/V diffractometer | Rint = 0.037 |
5193 measured reflections | 2 standard reflections every 198 reflections |
4631 independent reflections | intensity decay: none |
3592 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.27 e Å−3 |
4631 reflections | Δρmin = −0.22 e Å−3 |
277 parameters |
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 > 2σ(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 | ||
N1 | 0.30261 (6) | 0.37224 (17) | 0.56068 (8) | 0.0268 (3) | |
H1 | 0.3356 (9) | 0.439 (3) | 0.5864 (13) | 0.042 (5)* | |
C2 | 0.28084 (7) | 0.21436 (19) | 0.59395 (10) | 0.0278 (3) | |
C3 | 0.22269 (7) | 0.15625 (19) | 0.53190 (10) | 0.0279 (3) | |
C4 | 0.20900 (7) | 0.28679 (19) | 0.45834 (10) | 0.0267 (3) | |
C5 | 0.25936 (7) | 0.41963 (19) | 0.47815 (10) | 0.0261 (3) | |
N2 | 0.38371 (6) | 0.04176 (16) | 0.66530 (8) | 0.0278 (3) | |
C21 | 0.31864 (7) | 0.1282 (2) | 0.68238 (10) | 0.0308 (3) | |
H21A | 0.3294 | 0.2200 | 0.7329 | 0.037* | |
H21B | 0.2877 | 0.0380 | 0.7059 | 0.037* | |
C22 | 0.44372 (7) | 0.1384 (2) | 0.65426 (9) | 0.0274 (3) | |
C23 | 0.49587 (7) | 0.00499 (19) | 0.63188 (9) | 0.0261 (3) | |
C24 | 0.56346 (7) | 0.0286 (2) | 0.61316 (10) | 0.0314 (3) | |
H24 | 0.5846 | 0.1434 | 0.6157 | 0.038* | |
C25 | 0.59925 (7) | −0.1239 (2) | 0.59037 (11) | 0.0347 (3) | |
H25 | 0.6459 | −0.1129 | 0.5773 | 0.042* | |
C26 | 0.56792 (8) | −0.2915 (2) | 0.58645 (11) | 0.0336 (3) | |
H26 | 0.5934 | −0.3927 | 0.5701 | 0.040* | |
C27 | 0.49967 (8) | −0.3138 (2) | 0.60609 (10) | 0.0305 (3) | |
H27 | 0.4782 | −0.4282 | 0.6038 | 0.037* | |
C28 | 0.46492 (7) | −0.16269 (19) | 0.62892 (9) | 0.0255 (3) | |
C29 | 0.39265 (7) | −0.14212 (19) | 0.65286 (10) | 0.0266 (3) | |
O1 | 0.44822 (6) | 0.29938 (14) | 0.66130 (7) | 0.0349 (3) | |
O2 | 0.34920 (5) | −0.25493 (15) | 0.66160 (8) | 0.0352 (3) | |
C31 | 0.18076 (8) | −0.0095 (2) | 0.54301 (11) | 0.0333 (3) | |
H31A | 0.2102 | −0.0952 | 0.5844 | 0.040* | |
H31B | 0.1682 | −0.0659 | 0.4794 | 0.040* | |
C32 | 0.11410 (9) | 0.0258 (3) | 0.58610 (14) | 0.0481 (4) | |
H32A | 0.1261 | 0.0807 | 0.6494 | 0.072* | |
H32B | 0.0896 | −0.0873 | 0.5924 | 0.072* | |
H32C | 0.0838 | 0.1068 | 0.5442 | 0.072* | |
C41 | 0.15170 (8) | 0.2780 (2) | 0.37443 (11) | 0.0352 (3) | |
H41A | 0.1266 | 0.3922 | 0.3680 | 0.053* | |
H41B | 0.1191 | 0.1820 | 0.3846 | 0.053* | |
H41C | 0.1720 | 0.2541 | 0.3159 | 0.053* | |
C51 | 0.27361 (7) | 0.5849 (2) | 0.43034 (10) | 0.0274 (3) | |
C52 | 0.22978 (7) | 0.7991 (2) | 0.31376 (10) | 0.0289 (3) | |
H52A | 0.2669 | 0.7876 | 0.2726 | 0.035* | |
H52B | 0.2435 | 0.8941 | 0.3616 | 0.035* | |
C53 | 0.16146 (7) | 0.84587 (19) | 0.25394 (10) | 0.0265 (3) | |
C54 | 0.09744 (7) | 0.8122 (2) | 0.28520 (11) | 0.0327 (3) | |
H54 | 0.0963 | 0.7523 | 0.3443 | 0.039* | |
C55 | 0.03544 (8) | 0.8655 (2) | 0.23054 (12) | 0.0396 (4) | |
H55 | −0.0080 | 0.8423 | 0.2523 | 0.047* | |
C56 | 0.03679 (9) | 0.9526 (2) | 0.14419 (13) | 0.0433 (4) | |
H56 | −0.0056 | 0.9900 | 0.1069 | 0.052* | |
C57 | 0.09977 (9) | 0.9850 (2) | 0.11242 (12) | 0.0407 (4) | |
H57 | 0.1006 | 1.0440 | 0.0529 | 0.049* | |
C58 | 0.16192 (8) | 0.9320 (2) | 0.16687 (11) | 0.0318 (3) | |
H58 | 0.2051 | 0.9548 | 0.1444 | 0.038* | |
O3 | 0.32659 (5) | 0.67202 (16) | 0.44929 (8) | 0.0395 (3) | |
O4 | 0.22085 (5) | 0.63129 (14) | 0.36163 (7) | 0.0312 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0231 (6) | 0.0301 (6) | 0.0275 (6) | 0.0005 (5) | 0.0049 (5) | 0.0009 (5) |
C2 | 0.0278 (7) | 0.0286 (7) | 0.0284 (7) | 0.0044 (6) | 0.0094 (5) | 0.0017 (6) |
C3 | 0.0277 (7) | 0.0272 (7) | 0.0299 (7) | 0.0033 (6) | 0.0078 (5) | −0.0012 (6) |
C4 | 0.0255 (6) | 0.0267 (7) | 0.0286 (7) | 0.0027 (5) | 0.0062 (5) | −0.0014 (6) |
C5 | 0.0232 (6) | 0.0287 (7) | 0.0274 (7) | 0.0030 (5) | 0.0062 (5) | 0.0009 (6) |
N2 | 0.0267 (6) | 0.0274 (6) | 0.0290 (6) | 0.0006 (5) | 0.0034 (5) | 0.0037 (5) |
C21 | 0.0318 (7) | 0.0352 (8) | 0.0265 (7) | 0.0049 (6) | 0.0081 (6) | 0.0032 (6) |
C22 | 0.0318 (7) | 0.0287 (7) | 0.0205 (6) | −0.0024 (6) | 0.0003 (5) | 0.0046 (5) |
C23 | 0.0267 (7) | 0.0283 (7) | 0.0221 (6) | −0.0020 (5) | −0.0001 (5) | 0.0036 (5) |
C24 | 0.0292 (7) | 0.0352 (8) | 0.0289 (7) | −0.0073 (6) | 0.0010 (6) | 0.0044 (6) |
C25 | 0.0240 (7) | 0.0480 (9) | 0.0320 (7) | −0.0011 (6) | 0.0039 (6) | 0.0046 (7) |
C26 | 0.0324 (7) | 0.0374 (9) | 0.0310 (7) | 0.0076 (6) | 0.0048 (6) | 0.0028 (6) |
C27 | 0.0339 (7) | 0.0282 (7) | 0.0295 (7) | −0.0005 (6) | 0.0047 (6) | 0.0023 (6) |
C28 | 0.0258 (6) | 0.0272 (7) | 0.0231 (6) | −0.0022 (5) | 0.0018 (5) | 0.0053 (5) |
C29 | 0.0274 (7) | 0.0287 (7) | 0.0236 (6) | −0.0009 (6) | 0.0029 (5) | 0.0034 (5) |
O1 | 0.0457 (6) | 0.0233 (5) | 0.0349 (6) | −0.0034 (4) | 0.0031 (5) | 0.0017 (4) |
O2 | 0.0331 (5) | 0.0338 (6) | 0.0406 (6) | −0.0086 (5) | 0.0116 (5) | 0.0004 (5) |
C31 | 0.0373 (8) | 0.0264 (8) | 0.0362 (8) | 0.0001 (6) | 0.0056 (6) | 0.0016 (6) |
C32 | 0.0444 (10) | 0.0386 (10) | 0.0652 (12) | −0.0061 (8) | 0.0209 (9) | 0.0044 (9) |
C41 | 0.0363 (8) | 0.0313 (8) | 0.0355 (8) | −0.0032 (6) | −0.0030 (6) | 0.0001 (6) |
C51 | 0.0251 (6) | 0.0312 (8) | 0.0267 (7) | 0.0016 (6) | 0.0069 (5) | −0.0002 (6) |
C52 | 0.0281 (7) | 0.0280 (7) | 0.0314 (7) | −0.0037 (6) | 0.0072 (6) | 0.0039 (6) |
C53 | 0.0294 (7) | 0.0219 (7) | 0.0292 (7) | −0.0010 (5) | 0.0074 (5) | −0.0012 (5) |
C54 | 0.0312 (7) | 0.0357 (8) | 0.0324 (7) | 0.0006 (6) | 0.0089 (6) | 0.0035 (6) |
C55 | 0.0278 (7) | 0.0466 (10) | 0.0450 (9) | 0.0006 (7) | 0.0077 (6) | −0.0003 (8) |
C56 | 0.0367 (8) | 0.0424 (10) | 0.0479 (9) | 0.0064 (7) | −0.0035 (7) | 0.0073 (8) |
C57 | 0.0473 (9) | 0.0357 (9) | 0.0378 (8) | −0.0018 (7) | 0.0020 (7) | 0.0125 (7) |
C58 | 0.0347 (7) | 0.0286 (8) | 0.0331 (7) | −0.0038 (6) | 0.0088 (6) | 0.0035 (6) |
O3 | 0.0293 (5) | 0.0459 (7) | 0.0421 (6) | −0.0093 (5) | 0.0011 (5) | 0.0114 (5) |
O4 | 0.0287 (5) | 0.0280 (5) | 0.0355 (5) | −0.0026 (4) | −0.0002 (4) | 0.0060 (4) |
N1—C2 | 1.3599 (19) | C29—O2 | 1.2093 (17) |
N1—C5 | 1.3781 (18) | C31—C32 | 1.524 (2) |
N1—H1 | 0.851 (18) | C31—H31A | 0.9900 |
C2—C3 | 1.391 (2) | C31—H31B | 0.9900 |
C2—C21 | 1.498 (2) | C32—H32A | 0.9800 |
C3—C4 | 1.422 (2) | C32—H32B | 0.9800 |
C3—C31 | 1.502 (2) | C32—H32C | 0.9800 |
C4—C5 | 1.391 (2) | C41—H41A | 0.9800 |
C4—C41 | 1.501 (2) | C41—H41B | 0.9800 |
C5—C51 | 1.453 (2) | C41—H41C | 0.9800 |
N2—C22 | 1.3942 (18) | C51—O3 | 1.2107 (17) |
N2—C29 | 1.401 (2) | C51—O4 | 1.3471 (17) |
N2—C21 | 1.4643 (18) | C52—O4 | 1.4475 (18) |
C21—H21A | 0.9900 | C52—C53 | 1.502 (2) |
C21—H21B | 0.9900 | C52—H52A | 0.9900 |
C22—O1 | 1.2106 (19) | C52—H52B | 0.9900 |
C22—C23 | 1.484 (2) | C53—C58 | 1.388 (2) |
C23—C24 | 1.380 (2) | C53—C54 | 1.395 (2) |
C23—C28 | 1.388 (2) | C54—C55 | 1.387 (2) |
C24—C25 | 1.395 (2) | C54—H54 | 0.9500 |
C24—H24 | 0.9500 | C55—C56 | 1.385 (2) |
C25—C26 | 1.390 (2) | C55—H55 | 0.9500 |
C25—H25 | 0.9500 | C56—C57 | 1.377 (2) |
C26—C27 | 1.396 (2) | C56—H56 | 0.9500 |
C26—H26 | 0.9500 | C57—C58 | 1.387 (2) |
C27—C28 | 1.376 (2) | C57—H57 | 0.9500 |
C27—H27 | 0.9500 | C58—H58 | 0.9500 |
C28—C29 | 1.4910 (19) | ||
C2—N1—C5 | 109.57 (12) | N2—C29—C28 | 105.44 (11) |
C2—N1—H1 | 127.9 (12) | C3—C31—C32 | 113.44 (13) |
C5—N1—H1 | 122.4 (13) | C3—C31—H31A | 108.9 |
N1—C2—C3 | 108.45 (12) | C32—C31—H31A | 108.9 |
N1—C2—C21 | 121.55 (13) | C3—C31—H31B | 108.9 |
C3—C2—C21 | 129.98 (14) | C32—C31—H31B | 108.9 |
C2—C3—C4 | 107.04 (13) | H31A—C31—H31B | 107.7 |
C2—C3—C31 | 126.27 (13) | C31—C32—H32A | 109.5 |
C4—C3—C31 | 126.64 (13) | C31—C32—H32B | 109.5 |
C5—C4—C3 | 107.04 (13) | H32A—C32—H32B | 109.5 |
C5—C4—C41 | 127.23 (13) | C31—C32—H32C | 109.5 |
C3—C4—C41 | 125.72 (13) | H32A—C32—H32C | 109.5 |
N1—C5—C4 | 107.91 (13) | H32B—C32—H32C | 109.5 |
N1—C5—C51 | 118.59 (12) | C4—C41—H41A | 109.5 |
C4—C5—C51 | 133.50 (13) | C4—C41—H41B | 109.5 |
C22—N2—C29 | 112.07 (12) | H41A—C41—H41B | 109.5 |
C22—N2—C21 | 122.48 (13) | C4—C41—H41C | 109.5 |
C29—N2—C21 | 125.36 (12) | H41A—C41—H41C | 109.5 |
N2—C21—C2 | 112.37 (11) | H41B—C41—H41C | 109.5 |
N2—C21—H21A | 109.1 | O3—C51—O4 | 123.25 (13) |
C2—C21—H21A | 109.1 | O3—C51—C5 | 124.48 (13) |
N2—C21—H21B | 109.1 | O4—C51—C5 | 112.26 (12) |
C2—C21—H21B | 109.1 | O4—C52—C53 | 108.05 (11) |
H21A—C21—H21B | 107.9 | O4—C52—H52A | 110.1 |
O1—C22—N2 | 123.91 (14) | C53—C52—H52A | 110.1 |
O1—C22—C23 | 130.06 (14) | O4—C52—H52B | 110.1 |
N2—C22—C23 | 106.02 (12) | C53—C52—H52B | 110.1 |
C24—C23—C28 | 121.69 (14) | H52A—C52—H52B | 108.4 |
C24—C23—C22 | 130.13 (14) | C58—C53—C54 | 118.85 (13) |
C28—C23—C22 | 108.15 (12) | C58—C53—C52 | 119.22 (13) |
C23—C24—C25 | 116.95 (14) | C54—C53—C52 | 121.87 (13) |
C23—C24—H24 | 121.5 | C55—C54—C53 | 120.45 (14) |
C25—C24—H24 | 121.5 | C55—C54—H54 | 119.8 |
C26—C25—C24 | 121.29 (14) | C53—C54—H54 | 119.8 |
C26—C25—H25 | 119.4 | C56—C55—C54 | 120.01 (15) |
C24—C25—H25 | 119.4 | C56—C55—H55 | 120.0 |
C25—C26—C27 | 121.21 (15) | C54—C55—H55 | 120.0 |
C25—C26—H26 | 119.4 | C57—C56—C55 | 119.88 (15) |
C27—C26—H26 | 119.4 | C57—C56—H56 | 120.1 |
C28—C27—C26 | 117.06 (14) | C55—C56—H56 | 120.1 |
C28—C27—H27 | 121.5 | C56—C57—C58 | 120.30 (15) |
C26—C27—H27 | 121.5 | C56—C57—H57 | 119.9 |
C27—C28—C23 | 121.79 (13) | C58—C57—H57 | 119.9 |
C27—C28—C29 | 129.94 (13) | C57—C58—C53 | 120.50 (14) |
C23—C28—C29 | 108.27 (12) | C57—C58—H58 | 119.8 |
O2—C29—N2 | 124.94 (13) | C53—C58—H58 | 119.8 |
O2—C29—C28 | 129.62 (14) | C51—O4—C52 | 115.49 (11) |
C5—N1—C2—C3 | 0.47 (15) | C26—C27—C28—C23 | 0.4 (2) |
C5—N1—C2—C21 | 179.14 (12) | C26—C27—C28—C29 | 179.78 (13) |
N1—C2—C3—C4 | −0.34 (15) | C24—C23—C28—C27 | −0.8 (2) |
C21—C2—C3—C4 | −178.86 (13) | C22—C23—C28—C27 | 177.52 (12) |
N1—C2—C3—C31 | −178.12 (13) | C24—C23—C28—C29 | 179.70 (12) |
C21—C2—C3—C31 | 3.4 (2) | C22—C23—C28—C29 | −2.01 (14) |
C2—C3—C4—C5 | 0.08 (15) | C22—N2—C29—O2 | 177.65 (13) |
C31—C3—C4—C5 | 177.86 (13) | C21—N2—C29—O2 | −5.7 (2) |
C2—C3—C4—C41 | 178.76 (13) | C22—N2—C29—C28 | −1.69 (15) |
C31—C3—C4—C41 | −3.5 (2) | C21—N2—C29—C28 | 174.93 (11) |
C2—N1—C5—C4 | −0.42 (15) | C27—C28—C29—O2 | 3.5 (2) |
C2—N1—C5—C51 | −179.78 (12) | C23—C28—C29—O2 | −177.01 (14) |
C3—C4—C5—N1 | 0.20 (15) | C27—C28—C29—N2 | −177.20 (14) |
C41—C4—C5—N1 | −178.45 (13) | C23—C28—C29—N2 | 2.28 (15) |
C3—C4—C5—C51 | 179.43 (14) | C2—C3—C31—C32 | 98.71 (18) |
C41—C4—C5—C51 | 0.8 (3) | C4—C3—C31—C32 | −78.65 (19) |
C22—N2—C21—C2 | 74.63 (17) | N1—C5—C51—O3 | 11.4 (2) |
C29—N2—C21—C2 | −101.66 (16) | C4—C5—C51—O3 | −167.77 (15) |
N1—C2—C21—N2 | −76.22 (17) | N1—C5—C51—O4 | −168.68 (12) |
C3—C2—C21—N2 | 102.13 (17) | C4—C5—C51—O4 | 12.2 (2) |
C29—N2—C22—O1 | 179.62 (13) | O4—C52—C53—C58 | −145.08 (13) |
C21—N2—C22—O1 | 2.9 (2) | O4—C52—C53—C54 | 37.72 (18) |
C29—N2—C22—C23 | 0.50 (15) | C58—C53—C54—C55 | −0.6 (2) |
C21—N2—C22—C23 | −176.23 (11) | C52—C53—C54—C55 | 176.57 (15) |
O1—C22—C23—C24 | 0.0 (2) | C53—C54—C55—C56 | 0.1 (3) |
N2—C22—C23—C24 | 179.09 (13) | C54—C55—C56—C57 | 0.5 (3) |
O1—C22—C23—C28 | −178.05 (14) | C55—C56—C57—C58 | −0.5 (3) |
N2—C22—C23—C28 | 0.99 (14) | C56—C57—C58—C53 | −0.1 (3) |
C28—C23—C24—C25 | 0.5 (2) | C54—C53—C58—C57 | 0.6 (2) |
C22—C23—C24—C25 | −177.42 (13) | C52—C53—C58—C57 | −176.68 (14) |
C23—C24—C25—C26 | 0.2 (2) | O3—C51—O4—C52 | −2.8 (2) |
C24—C25—C26—C27 | −0.6 (2) | C5—C51—O4—C52 | 177.22 (11) |
C25—C26—C27—C28 | 0.3 (2) | C53—C52—O4—C51 | −169.44 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.851 (18) | 2.506 (17) | 3.0130 (18) | 119.1 (15) |
N1—H1···O2i | 0.851 (18) | 2.520 (19) | 3.201 (2) | 137.8 (15) |
C24—H24···O3ii | 0.95 | 2.48 | 3.293 (2) | 144 |
C27—H27···O1iii | 0.95 | 2.30 | 3.193 (2) | 157 |
C41—H41A···O4 | 0.98 | 2.56 | 2.979 (2) | 106 |
C52—H52A···O2iv | 0.99 | 2.40 | 3.3857 (19) | 175 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z; (iv) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C24H22N2O4 |
Mr | 402.44 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 130 |
a, b, c (Å) | 19.322 (6), 7.482 (4), 14.104 (3) |
β (°) | 98.27 (2) |
V (Å3) | 2017.8 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.44 × 0.40 |
Data collection | |
Diffractometer | Siemens R3m/V |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5193, 4631, 3592 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.118, 1.01 |
No. of reflections | 4631 |
No. of parameters | 277 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.22 |
Computer programs: P3/PC (Siemens, 1995a), P3/PC, XDISK (Siemens, 1995b), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1995b), SHELXL97 and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.851 (18) | 2.506 (17) | 3.0130 (18) | 119.1 (15) |
N1—H1···O2i | 0.851 (18) | 2.520 (19) | 3.201 (2) | 137.8 (15) |
C24—H24···O3ii | 0.95 | 2.48 | 3.293 (2) | 143.9 |
C27—H27···O1iii | 0.95 | 2.30 | 3.193 (2) | 156.7 |
C41—H41A···O4 | 0.98 | 2.56 | 2.979 (2) | 105.5 |
C52—H52A···O2iv | 0.99 | 2.40 | 3.3857 (19) | 175.1 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z; (iv) x, −y+1/2, z−1/2. |
In continuation of studies on the hydrogen bonding pattern in pyrroles (Senge & Smith, 2005), dipyrromethanes (Senge, 2005) and porphyrins (Senge, 2000) the title compound was investigated for N–H···O and C–H···O interactions using the criteria put forward by Steiner (1997).
The structure is characterized by an intramolecular hydrogen bond between the pyrrole hydrogen and O1 from the phthalimido group [N1–H1···O1, 2.506 (17) Å, 119.1 (15)°]. The pyrrole hydrogen atom is also involved in intermolecular hydrogen bond, which is formed with the carbonyl oxygen atom (O2) of the phthalimido group not involved in the intramolecular hydrogen bond [N1–H1···O2, 2.520 (19) Å, 137.8 (15)°]. As indicated by their bond lenghts, both hydrogen bonds are relatively weak. The phthalimido group also participates in C–H···O interactions. Atom O1 is in close contact with an aromatic C–H unit [C27–H27···O1 = 2.30 (2) Å], while O2 is in close contact to an aliphatic CH2-group [C52–H52···O2 = 2.40 (2) Å]. The benzylic ester group is only involved in a contact to another aromatic C–H unit [C24–H24···O3 = 2.48 (2) Å]. Thus, arrangement of the molecules in the crystal is dominated by intermolecular contacts involving the phthalimido groups. These arrange in parallel layers with the benzylester groups forming an outer rim of this ladder-type arrangement.