Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037385/rt2013sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037385/rt2013Isup2.hkl |
CCDC reference: 660190
Key indicators
- Single-crystal X-ray study
- T = 90 K
- Mean (C-C) = 0.002 Å
- R factor = 0.051
- wR factor = 0.131
- Data-to-parameter ratio = 24.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Bonnett et al. (1972); Lin et al. (1996); Bennis & Gallagher (1998); Gallagher & Moriarty (1999); Patra et al. (2002); Senge (2000, 2005a,b); Senge & Smith (2005); Shin et al. (2004). The compound was prepared as described by Lazzeri & Durantini (2003); crystals were handled as decribed by Hope (1994). The hydrogen-bonding analysis followed the criteria set out by Steiner (1997).
Crystals were handled as described by Hope (1994). The compound was prepared as described earlier (Lazzeri & Durantini, 2003) and 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 0.88–1.00 Å and Uiso (H) = 1.2 Ueq (C) for CH and NH groups and Uiso (H) = 1.5 Ueq (C) for methyl groups.
Dipyrromethanes are central synthetic building blocks for porphyrins which exhibit a rich structural chemistry (Senge, 2005a; Shin et al., 2004). In continuation of our studies on the hydrogen bonding pattern in porphyrins and related building blocks (Senge, 2000, 2005b; Senge & Smith, 2005). We report here the structure of a dipyrromethane with an acceptor substituted meso position. Using the criteria defined by Steiner (1997) the title compound was investigated for N–H···O and C–H···O interactions. The compound forms infinite chains through hydrogen bonding of O1 to a neighboring pyrrole NH [N1–H1···O1, 2.891 (2) Å, 171°] and the acetamido NH [N3–H3···O2, 2.894 (2) Å, 169°]. Thus, the acetamido group on the meso substituent functions as the connecting unit in the supramolecular structure, primarily through the 3-center hydrogen bond system involving O1.
The pyrrole N–H unit of ring 2 is not involved in any hydrogen bonding. As can be seen in Fig. 1 the two pyrrole rings point in opposite directions and the two pyrrole planes are tilted by 60.1°. As shown in Fig. 2, the N2 unit is effectively shielded by the backbone of the neighboring chain of molecules and points towards the back of pyrrole ring 1 in the neighboring unit, where no acceptor atoms are present. In addition, the carbonyl oxygen atom is involved in a weak intramolecular interaction with the neighboring aryl group [C55–H55A···O1 = 2.55 (2) Å]. Related structures have been reported (Bonnett et al., 1972; Lin et al., 1996; Bennis & Gallagher, 1998; Gallagher & Moriarty, 1999; Patra et al., 2002).
For related literature, see: Bonnett et al. (1972); Lin et al. (1996); Bennis & Gallagher (1998); Gallagher & Moriarty (1999); Patra et al. (2002); Senge (2000, 2005a,b); Senge & Smith (2005); Shin et al. (2004). The compound was prepared as described by Lazzeri & Durantini (2003); crystals were handled as decribed by Hope (1994). The hydrogen-bonding analysis followed the criteria set out by Steiner (1997).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Siemens, 1995); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C17H17N3O | F(000) = 592 |
Mr = 279.34 | Dx = 1.320 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3237 reflections |
a = 7.4007 (6) Å | θ = 5.6–62.6° |
b = 24.858 (2) Å | µ = 0.09 mm−1 |
c = 8.2690 (7) Å | T = 90 K |
β = 112.490 (2)° | Plate, yellow |
V = 1405.5 (2) Å3 | 0.50 × 0.40 × 0.01 mm |
Z = 4 |
Bruker SMART APEX II diffractometer | 4656 independent reflections |
Radiation source: sealed tube | 3167 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
Detector resolution: 8.3 pixels mm-1 | θmax = 31.5°, θmin = 2.8° |
φ and ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −36→36 |
Tmin = 0.96, Tmax = 0.99 | l = −12→12 |
20557 measured reflections |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0603P)2 + 0.3541P] where P = (Fo2 + 2Fc2)/3 |
4656 reflections | (Δ/σ)max = 0.001 |
191 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C17H17N3O | V = 1405.5 (2) Å3 |
Mr = 279.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.4007 (6) Å | µ = 0.09 mm−1 |
b = 24.858 (2) Å | T = 90 K |
c = 8.2690 (7) Å | 0.50 × 0.40 × 0.01 mm |
β = 112.490 (2)° |
Bruker SMART APEX II diffractometer | 4656 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3167 reflections with I > 2σ(I) |
Tmin = 0.96, Tmax = 0.99 | Rint = 0.061 |
20557 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.41 e Å−3 |
4656 reflections | Δρmin = −0.26 e Å−3 |
191 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 > 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. All hydrogen atoms were located in difference maps. All hydrogen atoms were located in difference maps. No H-acceptor was found for N2. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.09109 (16) | 0.41540 (5) | 0.30239 (15) | 0.0171 (2) | |
H1A | 0.0414 | 0.3836 | 0.2631 | 0.020* | |
N2 | 0.29445 (17) | 0.43496 (5) | 0.84943 (16) | 0.0194 (2) | |
H2A | 0.1802 | 0.4496 | 0.7890 | 0.023* | |
C1 | 0.0471 (2) | 0.46203 (6) | 0.2072 (2) | 0.0195 (3) | |
H1B | −0.0407 | 0.4655 | 0.0887 | 0.023* | |
C2 | 0.1523 (2) | 0.50284 (6) | 0.31309 (19) | 0.0189 (3) | |
H2B | 0.1509 | 0.5396 | 0.2817 | 0.023* | |
C3 | 0.2638 (2) | 0.47978 (5) | 0.47852 (19) | 0.0181 (3) | |
H3A | 0.3503 | 0.4984 | 0.5784 | 0.022* | |
C4 | 0.22382 (18) | 0.42563 (5) | 0.46783 (18) | 0.0154 (3) | |
C5 | 0.30492 (19) | 0.38041 (5) | 0.59659 (18) | 0.0163 (3) | |
H5A | 0.1932 | 0.3562 | 0.5868 | 0.020* | |
C6 | 0.39253 (19) | 0.40006 (5) | 0.78285 (18) | 0.0165 (3) | |
C7 | 0.5625 (2) | 0.38611 (6) | 0.9176 (2) | 0.0205 (3) | |
H7A | 0.6598 | 0.3624 | 0.9105 | 0.025* | |
C8 | 0.5673 (2) | 0.41349 (6) | 1.0705 (2) | 0.0226 (3) | |
H8A | 0.6677 | 0.4113 | 1.1840 | 0.027* | |
C9 | 0.4008 (2) | 0.44351 (6) | 1.0236 (2) | 0.0217 (3) | |
H9A | 0.3651 | 0.4663 | 1.0986 | 0.026* | |
C51 | 0.45508 (19) | 0.34645 (5) | 0.55772 (18) | 0.0155 (3) | |
C52 | 0.5895 (2) | 0.37005 (6) | 0.4991 (2) | 0.0202 (3) | |
H52A | 0.5821 | 0.4075 | 0.4752 | 0.024* | |
C53 | 0.7340 (2) | 0.33949 (6) | 0.4753 (2) | 0.0202 (3) | |
H53A | 0.8263 | 0.3563 | 0.4375 | 0.024* | |
C54 | 0.74457 (19) | 0.28430 (5) | 0.50661 (17) | 0.0159 (3) | |
C55 | 0.6086 (2) | 0.25983 (5) | 0.56148 (19) | 0.0176 (3) | |
H55A | 0.6123 | 0.2221 | 0.5802 | 0.021* | |
C56 | 0.46718 (19) | 0.29128 (5) | 0.58853 (19) | 0.0177 (3) | |
H56A | 0.3767 | 0.2747 | 0.6290 | 0.021* | |
C57 | 0.98507 (19) | 0.21091 (5) | 0.55646 (18) | 0.0158 (3) | |
C58 | 1.1101 (2) | 0.18235 (6) | 0.4755 (2) | 0.0226 (3) | |
H58A | 1.2343 | 0.1717 | 0.5677 | 0.034* | |
H58B | 1.1358 | 0.2066 | 0.3932 | 0.034* | |
H58C | 1.0414 | 0.1503 | 0.4130 | 0.034* | |
N3 | 0.88981 (17) | 0.25458 (5) | 0.47060 (15) | 0.0174 (2) | |
H3B | 0.9199 | 0.2661 | 0.3833 | 0.021* | |
O1 | 0.97034 (14) | 0.19367 (4) | 0.69187 (13) | 0.0187 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0165 (5) | 0.0150 (5) | 0.0188 (6) | −0.0017 (4) | 0.0058 (5) | −0.0015 (4) |
N2 | 0.0149 (5) | 0.0209 (6) | 0.0222 (6) | 0.0029 (4) | 0.0070 (5) | −0.0013 (5) |
C1 | 0.0168 (6) | 0.0206 (7) | 0.0200 (7) | 0.0026 (5) | 0.0060 (6) | 0.0030 (5) |
C2 | 0.0171 (6) | 0.0155 (6) | 0.0242 (8) | 0.0025 (5) | 0.0080 (6) | 0.0032 (5) |
C3 | 0.0158 (6) | 0.0144 (6) | 0.0221 (7) | −0.0003 (5) | 0.0051 (5) | −0.0009 (5) |
C4 | 0.0131 (6) | 0.0143 (6) | 0.0191 (7) | 0.0016 (5) | 0.0063 (5) | 0.0007 (5) |
C5 | 0.0138 (6) | 0.0140 (6) | 0.0211 (7) | 0.0012 (5) | 0.0066 (5) | 0.0008 (5) |
C6 | 0.0158 (6) | 0.0155 (6) | 0.0206 (7) | 0.0014 (5) | 0.0095 (5) | 0.0023 (5) |
C7 | 0.0174 (6) | 0.0234 (7) | 0.0213 (7) | 0.0050 (5) | 0.0082 (6) | 0.0049 (6) |
C8 | 0.0205 (7) | 0.0282 (8) | 0.0182 (7) | 0.0013 (6) | 0.0065 (6) | 0.0037 (6) |
C9 | 0.0224 (7) | 0.0240 (7) | 0.0210 (7) | −0.0018 (5) | 0.0107 (6) | −0.0029 (6) |
C51 | 0.0144 (6) | 0.0148 (6) | 0.0161 (6) | 0.0020 (5) | 0.0047 (5) | −0.0003 (5) |
C52 | 0.0210 (6) | 0.0138 (6) | 0.0278 (8) | 0.0032 (5) | 0.0117 (6) | 0.0051 (6) |
C53 | 0.0206 (6) | 0.0178 (7) | 0.0265 (8) | 0.0037 (5) | 0.0140 (6) | 0.0065 (6) |
C54 | 0.0165 (6) | 0.0163 (6) | 0.0151 (6) | 0.0038 (5) | 0.0063 (5) | 0.0010 (5) |
C55 | 0.0188 (6) | 0.0122 (6) | 0.0220 (7) | 0.0014 (5) | 0.0080 (6) | 0.0009 (5) |
C56 | 0.0157 (6) | 0.0148 (6) | 0.0236 (7) | −0.0005 (5) | 0.0086 (6) | 0.0013 (5) |
C57 | 0.0153 (6) | 0.0141 (6) | 0.0184 (7) | 0.0005 (5) | 0.0068 (5) | −0.0019 (5) |
C58 | 0.0239 (7) | 0.0201 (7) | 0.0281 (8) | 0.0057 (6) | 0.0147 (6) | −0.0004 (6) |
N3 | 0.0193 (5) | 0.0183 (6) | 0.0173 (6) | 0.0049 (4) | 0.0101 (5) | 0.0030 (4) |
O1 | 0.0218 (5) | 0.0170 (5) | 0.0185 (5) | 0.0042 (4) | 0.0090 (4) | 0.0026 (4) |
N1—C4 | 1.3686 (18) | C8—H8A | 0.9500 |
N1—C1 | 1.3685 (18) | C9—H9A | 0.9500 |
N1—H1A | 0.8800 | C51—C56 | 1.3914 (18) |
N2—C9 | 1.368 (2) | C51—C52 | 1.3917 (18) |
N2—C6 | 1.3741 (17) | C52—C53 | 1.3859 (19) |
N2—H2A | 0.8800 | C52—H52A | 0.9500 |
C1—C2 | 1.371 (2) | C53—C54 | 1.3926 (19) |
C1—H1B | 0.9500 | C53—H53A | 0.9500 |
C2—C3 | 1.420 (2) | C54—C55 | 1.3921 (18) |
C2—H2B | 0.9500 | C54—N3 | 1.4265 (16) |
C3—C4 | 1.3737 (19) | C55—C56 | 1.3913 (18) |
C3—H3A | 0.9500 | C55—H55A | 0.9500 |
C4—C5 | 1.5061 (19) | C56—H56A | 0.9500 |
C5—C6 | 1.506 (2) | C57—O1 | 1.2421 (16) |
C5—C51 | 1.5245 (18) | C57—N3 | 1.3402 (17) |
C5—H5A | 1.0000 | C57—C58 | 1.5110 (18) |
C6—C7 | 1.368 (2) | C58—H58A | 0.9800 |
C7—C8 | 1.424 (2) | C58—H58B | 0.9800 |
C7—H7A | 0.9500 | C58—H58C | 0.9800 |
C8—C9 | 1.364 (2) | N3—H3B | 0.8800 |
C4—N1—C1 | 109.84 (12) | C8—C9—N2 | 107.93 (13) |
C4—N1—H1A | 125.1 | C8—C9—H9A | 126.0 |
C1—N1—H1A | 125.1 | N2—C9—H9A | 126.0 |
C9—N2—C6 | 109.90 (12) | C56—C51—C52 | 118.34 (12) |
C9—N2—H2A | 125.1 | C56—C51—C5 | 120.55 (12) |
C6—N2—H2A | 125.1 | C52—C51—C5 | 121.04 (12) |
N1—C1—C2 | 107.90 (13) | C53—C52—C51 | 120.76 (13) |
N1—C1—H1B | 126.0 | C53—C52—H52A | 119.6 |
C2—C1—H1B | 126.0 | C51—C52—H52A | 119.6 |
C1—C2—C3 | 107.16 (13) | C52—C53—C54 | 120.35 (12) |
C1—C2—H2B | 126.4 | C52—C53—H53A | 119.8 |
C3—C2—H2B | 126.4 | C54—C53—H53A | 119.8 |
C4—C3—C2 | 107.58 (13) | C55—C54—C53 | 119.65 (12) |
C4—C3—H3A | 126.2 | C55—C54—N3 | 122.55 (12) |
C2—C3—H3A | 126.2 | C53—C54—N3 | 117.70 (12) |
N1—C4—C3 | 107.51 (12) | C54—C55—C56 | 119.26 (12) |
N1—C4—C5 | 120.50 (12) | C54—C55—H55A | 120.4 |
C3—C4—C5 | 131.91 (13) | C56—C55—H55A | 120.4 |
C4—C5—C6 | 112.35 (11) | C51—C56—C55 | 121.61 (12) |
C4—C5—C51 | 112.94 (11) | C51—C56—H56A | 119.2 |
C6—C5—C51 | 109.38 (11) | C55—C56—H56A | 119.2 |
C4—C5—H5A | 107.3 | O1—C57—N3 | 123.18 (12) |
C6—C5—H5A | 107.3 | O1—C57—C58 | 121.15 (12) |
C51—C5—H5A | 107.3 | N3—C57—C58 | 115.66 (12) |
C7—C6—N2 | 107.19 (13) | C57—C58—H58A | 109.5 |
C7—C6—C5 | 130.77 (12) | C57—C58—H58B | 109.5 |
N2—C6—C5 | 121.86 (12) | H58A—C58—H58B | 109.5 |
C6—C7—C8 | 107.76 (12) | C57—C58—H58C | 109.5 |
C6—C7—H7A | 126.1 | H58A—C58—H58C | 109.5 |
C8—C7—H7A | 126.1 | H58B—C58—H58C | 109.5 |
C9—C8—C7 | 107.22 (13) | C57—N3—C54 | 126.48 (11) |
C9—C8—H8A | 126.4 | C57—N3—H3B | 116.8 |
C7—C8—H8A | 126.4 | C54—N3—H3B | 116.8 |
C4—N1—C1—C2 | −0.28 (15) | C7—C8—C9—N2 | 0.71 (17) |
N1—C1—C2—C3 | −0.04 (15) | C6—N2—C9—C8 | −0.77 (16) |
C1—C2—C3—C4 | 0.34 (15) | C4—C5—C51—C56 | −144.69 (13) |
C1—N1—C4—C3 | 0.49 (15) | C6—C5—C51—C56 | 89.39 (15) |
C1—N1—C4—C5 | −176.75 (11) | C4—C5—C51—C52 | 38.56 (18) |
C2—C3—C4—N1 | −0.50 (15) | C6—C5—C51—C52 | −87.36 (15) |
C2—C3—C4—C5 | 176.30 (13) | C56—C51—C52—C53 | −1.2 (2) |
N1—C4—C5—C6 | −160.97 (11) | C5—C51—C52—C53 | 175.61 (14) |
C3—C4—C5—C6 | 22.6 (2) | C51—C52—C53—C54 | 1.2 (2) |
N1—C4—C5—C51 | 74.73 (15) | C52—C53—C54—C55 | 0.2 (2) |
C3—C4—C5—C51 | −101.74 (17) | C52—C53—C54—N3 | 176.64 (13) |
C9—N2—C6—C7 | 0.50 (16) | C53—C54—C55—C56 | −1.7 (2) |
C9—N2—C6—C5 | 176.08 (12) | N3—C54—C55—C56 | −177.90 (13) |
C4—C5—C6—C7 | −136.77 (15) | C52—C51—C56—C55 | −0.3 (2) |
C51—C5—C6—C7 | −10.5 (2) | C5—C51—C56—C55 | −177.10 (13) |
C4—C5—C6—N2 | 48.81 (16) | C54—C55—C56—C51 | 1.7 (2) |
C51—C5—C6—N2 | 175.06 (12) | O1—C57—N3—C54 | −7.1 (2) |
N2—C6—C7—C8 | −0.05 (16) | C58—C57—N3—C54 | 171.41 (13) |
C5—C6—C7—C8 | −175.09 (14) | C55—C54—N3—C57 | −36.2 (2) |
C6—C7—C8—C9 | −0.41 (17) | C53—C54—N3—C57 | 147.52 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.88 | 2.02 | 2.8914 (15) | 171 |
N3—H3B···O1ii | 0.88 | 2.03 | 2.8936 (15) | 169 |
C55—H55A···O1 | 0.95 | 2.55 | 2.9708 (17) | 107 |
Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H17N3O |
Mr | 279.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 90 |
a, b, c (Å) | 7.4007 (6), 24.858 (2), 8.2690 (7) |
β (°) | 112.490 (2) |
V (Å3) | 1405.5 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.40 × 0.01 |
Data collection | |
Diffractometer | Bruker SMART APEX II |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.96, 0.99 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20557, 4656, 3167 |
Rint | 0.061 |
(sin θ/λ)max (Å−1) | 0.736 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.131, 1.01 |
No. of reflections | 4656 |
No. of parameters | 191 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.26 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Siemens, 1995), SHELXTL and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.88 | 2.02 | 2.8914 (15) | 171.1 |
N3—H3B···O1ii | 0.88 | 2.03 | 2.8936 (15) | 168.9 |
C55—H55A···O1 | 0.95 | 2.55 | 2.9708 (17) | 107.1 |
Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) x, −y+1/2, z−1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
Dipyrromethanes are central synthetic building blocks for porphyrins which exhibit a rich structural chemistry (Senge, 2005a; Shin et al., 2004). In continuation of our studies on the hydrogen bonding pattern in porphyrins and related building blocks (Senge, 2000, 2005b; Senge & Smith, 2005). We report here the structure of a dipyrromethane with an acceptor substituted meso position. Using the criteria defined by Steiner (1997) the title compound was investigated for N–H···O and C–H···O interactions. The compound forms infinite chains through hydrogen bonding of O1 to a neighboring pyrrole NH [N1–H1···O1, 2.891 (2) Å, 171°] and the acetamido NH [N3–H3···O2, 2.894 (2) Å, 169°]. Thus, the acetamido group on the meso substituent functions as the connecting unit in the supramolecular structure, primarily through the 3-center hydrogen bond system involving O1.
The pyrrole N–H unit of ring 2 is not involved in any hydrogen bonding. As can be seen in Fig. 1 the two pyrrole rings point in opposite directions and the two pyrrole planes are tilted by 60.1°. As shown in Fig. 2, the N2 unit is effectively shielded by the backbone of the neighboring chain of molecules and points towards the back of pyrrole ring 1 in the neighboring unit, where no acceptor atoms are present. In addition, the carbonyl oxygen atom is involved in a weak intramolecular interaction with the neighboring aryl group [C55–H55A···O1 = 2.55 (2) Å]. Related structures have been reported (Bonnett et al., 1972; Lin et al., 1996; Bennis & Gallagher, 1998; Gallagher & Moriarty, 1999; Patra et al., 2002).