Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019915/hb2388sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019915/hb2388Isup2.hkl |
CCDC reference: 647711
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.096
- Data-to-parameter ratio = 8.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 10 Ang. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 30.00 From the CIF: _reflns_number_total 1086 Count of symmetry unique reflns 1088 Completeness (_total/calc) 99.82% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Commercially available indole-3-carboxaldehyde was recrystallized from ethanol to yield crystals of (I).
Anomalous dispersion was negligible and Friedel pairs were merged before refinement. All the H atoms were located in difference maps and their positions and Uiso values were freely refined.
The crystal structure of the title compound, (I), indole-3-carboxaldehyde was refined to R(F) = 0.053 from room-temperature diffraction measurements (Golubev & Kondrashev, 1984). This re-refinement represents an improvement; all H atoms were located and refined. In the crystal structure, the molecules are linked by an N—H···O hydrogen bond (Table 1) to form a helical C(6) chain that propagates along the c axis.
For related literature, see: Golubev & Kondrashev (1984).
Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).
C9H7NO | F(000) = 304 |
Mr = 145.16 | Dx = 1.376 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 4178 reflections |
a = 13.9016 (1) Å | θ = 2.9–29.8° |
b = 5.8655 (1) Å | µ = 0.09 mm−1 |
c = 8.5928 (1) Å | T = 173 K |
V = 700.66 (2) Å3 | Needle, colorless |
Z = 4 | 0.40 × 0.12 × 0.09 mm |
Bruker APEXII CCD diffractometer | 966 reflections with I > 2σ(I) |
Radiation source: medium-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 30.0°, θmin = 2.9° |
φ and ω scans | h = −19→19 |
11794 measured reflections | k = −8→8 |
1086 independent reflections | l = −12→12 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | All H-atom parameters refined |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0608P)2 + 0.0666P] where P = (Fo2 + 2Fc2)/3 |
1086 reflections | (Δ/σ)max = 0.001 |
128 parameters | Δρmax = 0.27 e Å−3 |
1 restraint | Δρmin = −0.16 e Å−3 |
C9H7NO | V = 700.66 (2) Å3 |
Mr = 145.16 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 13.9016 (1) Å | µ = 0.09 mm−1 |
b = 5.8655 (1) Å | T = 173 K |
c = 8.5928 (1) Å | 0.40 × 0.12 × 0.09 mm |
Bruker APEXII CCD diffractometer | 966 reflections with I > 2σ(I) |
11794 measured reflections | Rint = 0.041 |
1086 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 1 restraint |
wR(F2) = 0.096 | All H-atom parameters refined |
S = 1.10 | Δρmax = 0.27 e Å−3 |
1086 reflections | Δρmin = −0.16 e Å−3 |
128 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | 0.26655 (11) | 0.4245 (2) | 0.49999 (18) | 0.0281 (3) | |
N1 | 0.29363 (13) | 1.0779 (3) | 0.2067 (2) | 0.0246 (4) | |
C1 | 0.37908 (13) | 0.9581 (3) | 0.1919 (2) | 0.0203 (4) | |
C2 | 0.45965 (15) | 1.0078 (3) | 0.1013 (2) | 0.0244 (4) | |
C3 | 0.53265 (15) | 0.8489 (4) | 0.0993 (2) | 0.0257 (4) | |
C4 | 0.52637 (14) | 0.6458 (3) | 0.1862 (2) | 0.0258 (4) | |
C5 | 0.44695 (14) | 0.5987 (3) | 0.2777 (2) | 0.0216 (4) | |
C6 | 0.37122 (13) | 0.7567 (3) | 0.28066 (19) | 0.0190 (3) | |
C7 | 0.27630 (14) | 0.7600 (3) | 0.3492 (2) | 0.0201 (4) | |
C8 | 0.23266 (15) | 0.9593 (3) | 0.2984 (2) | 0.0244 (4) | |
C9 | 0.22880 (14) | 0.5972 (3) | 0.4472 (2) | 0.0219 (4) | |
H1 | 0.281 (2) | 1.216 (5) | 0.153 (4) | 0.047 (8)* | |
H2 | 0.4644 (19) | 1.148 (4) | 0.042 (3) | 0.028 (7)* | |
H3 | 0.590 (2) | 0.870 (5) | 0.027 (4) | 0.044 (9)* | |
H4 | 0.5805 (19) | 0.540 (5) | 0.183 (4) | 0.037 (7)* | |
H5 | 0.4432 (17) | 0.461 (4) | 0.334 (3) | 0.020 (6)* | |
H8 | 0.169 (2) | 1.007 (5) | 0.316 (4) | 0.036 (7)* | |
H9 | 0.1626 (17) | 0.638 (4) | 0.466 (3) | 0.022 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0332 (8) | 0.0218 (6) | 0.0292 (7) | 0.0000 (6) | 0.0022 (6) | 0.0071 (6) |
N1 | 0.0322 (9) | 0.0182 (7) | 0.0233 (8) | 0.0048 (6) | 0.0001 (7) | 0.0052 (6) |
C1 | 0.0276 (9) | 0.0155 (7) | 0.0179 (7) | −0.0005 (6) | −0.0032 (7) | 0.0002 (7) |
C2 | 0.0330 (10) | 0.0197 (9) | 0.0204 (8) | −0.0069 (7) | −0.0017 (8) | 0.0016 (7) |
C3 | 0.0234 (9) | 0.0307 (10) | 0.0231 (8) | −0.0064 (7) | 0.0010 (7) | −0.0013 (8) |
C4 | 0.0249 (9) | 0.0262 (9) | 0.0262 (9) | 0.0017 (7) | −0.0009 (8) | 0.0003 (8) |
C5 | 0.0258 (9) | 0.0187 (8) | 0.0203 (7) | 0.0005 (7) | −0.0028 (7) | 0.0016 (7) |
C6 | 0.0253 (8) | 0.0170 (7) | 0.0147 (7) | −0.0022 (6) | −0.0026 (7) | 0.0002 (6) |
C7 | 0.0254 (9) | 0.0179 (7) | 0.0169 (7) | 0.0009 (6) | −0.0006 (6) | 0.0016 (6) |
C8 | 0.0290 (10) | 0.0226 (8) | 0.0217 (8) | 0.0050 (7) | 0.0007 (7) | 0.0023 (7) |
C9 | 0.0257 (10) | 0.0220 (8) | 0.0182 (8) | −0.0001 (7) | 0.0028 (7) | −0.0020 (7) |
O1—C9 | 1.228 (2) | C4—C5 | 1.383 (3) |
N1—C8 | 1.350 (3) | C4—H4 | 0.98 (3) |
N1—C1 | 1.386 (2) | C5—C6 | 1.403 (3) |
N1—H1 | 0.95 (3) | C5—H5 | 0.94 (2) |
C1—C2 | 1.395 (3) | C6—C7 | 1.445 (3) |
C1—C6 | 1.410 (2) | C7—C8 | 1.388 (3) |
C2—C3 | 1.378 (3) | C7—C9 | 1.434 (3) |
C2—H2 | 0.97 (3) | C8—H8 | 0.94 (3) |
C3—C4 | 1.409 (3) | C9—H9 | 0.96 (2) |
C3—H3 | 1.02 (3) | ||
C8—N1—C1 | 109.28 (16) | C4—C5—C6 | 118.50 (17) |
C8—N1—H1 | 127.1 (19) | C4—C5—H5 | 120.5 (15) |
C1—N1—H1 | 123.5 (19) | C6—C5—H5 | 121.0 (15) |
N1—C1—C2 | 129.28 (17) | C5—C6—C1 | 119.06 (17) |
N1—C1—C6 | 108.00 (16) | C5—C6—C7 | 134.52 (16) |
C2—C1—C6 | 122.63 (17) | C1—C6—C7 | 106.27 (15) |
C3—C2—C1 | 117.20 (17) | C8—C7—C9 | 122.99 (18) |
C3—C2—H2 | 121.1 (16) | C8—C7—C6 | 106.37 (16) |
C1—C2—H2 | 121.7 (16) | C9—C7—C6 | 130.62 (17) |
C2—C3—C4 | 121.29 (19) | N1—C8—C7 | 110.08 (18) |
C2—C3—H3 | 120.1 (17) | N1—C8—H8 | 122.1 (18) |
C4—C3—H3 | 118.4 (17) | C7—C8—H8 | 127.6 (18) |
C5—C4—C3 | 121.32 (19) | O1—C9—C7 | 124.71 (18) |
C5—C4—H4 | 120.4 (17) | O1—C9—H9 | 123.4 (15) |
C3—C4—H4 | 118.3 (17) | C7—C9—H9 | 111.9 (15) |
C8—N1—C1—C2 | 175.59 (18) | N1—C1—C6—C7 | 0.35 (18) |
C8—N1—C1—C6 | −0.8 (2) | C2—C1—C6—C7 | −176.38 (17) |
N1—C1—C2—C3 | −175.09 (19) | C5—C6—C7—C8 | −174.9 (2) |
C6—C1—C2—C3 | 0.9 (3) | C1—C6—C7—C8 | 0.25 (19) |
C1—C2—C3—C4 | −0.5 (3) | C5—C6—C7—C9 | 3.4 (3) |
C2—C3—C4—C5 | −0.4 (3) | C1—C6—C7—C9 | 178.53 (19) |
C3—C4—C5—C6 | 1.0 (3) | C1—N1—C8—C7 | 1.0 (2) |
C4—C5—C6—C1 | −0.6 (3) | C9—C7—C8—N1 | −179.22 (18) |
C4—C5—C6—C7 | 174.08 (19) | C6—C7—C8—N1 | −0.8 (2) |
N1—C1—C6—C5 | 176.42 (17) | C8—C7—C9—O1 | −176.6 (2) |
C2—C1—C6—C5 | −0.3 (2) | C6—C7—C9—O1 | 5.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.95 (3) | 1.91 (3) | 2.826 (2) | 161 (3) |
Symmetry code: (i) −x+1/2, y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C9H7NO |
Mr | 145.16 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 173 |
a, b, c (Å) | 13.9016 (1), 5.8655 (1), 8.5928 (1) |
V (Å3) | 700.66 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.40 × 0.12 × 0.09 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11794, 1086, 966 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.096, 1.10 |
No. of reflections | 1086 |
No. of parameters | 128 |
No. of restraints | 1 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.27, −0.16 |
Computer programs: APEXII (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.95 (3) | 1.91 (3) | 2.826 (2) | 161 (3) |
Symmetry code: (i) −x+1/2, y+1, z−1/2. |
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The crystal structure of the title compound, (I), indole-3-carboxaldehyde was refined to R(F) = 0.053 from room-temperature diffraction measurements (Golubev & Kondrashev, 1984). This re-refinement represents an improvement; all H atoms were located and refined. In the crystal structure, the molecules are linked by an N—H···O hydrogen bond (Table 1) to form a helical C(6) chain that propagates along the c axis.