organic compounds
N-[2-(9H-Carbazol-9-yl)ethyl]-4-(methylsulfonyl)aniline
aDivision of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA, and bDepartment of Chemistry and Biochemistry, 100 West 18th Avenue, The Ohio State University, Columbus, OH 43210, USA
*Correspondence e-mail: li.728@osu.edu
In the title molecule, C21H20N2O2S, the dihedral angle between the mean plane of the carbazole ring system [maximum deviation = 0.021 (4) Å] and the benzene ring is 80.15 (6)°. In the crystal, molecules are linked by N—H⋯O and weak C—H⋯O hydrogen bonds into a C(8) chain along [001].
CCDC reference: 987458
Related literature
For a related structure, see: Lai et al. (2014) For the synthesis, see: Abdel-Magid et al. (1996); Hallberg et al. (1982). For hydrogen bond graph-set notation, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2013); cell SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
CCDC reference: 987458
10.1107/S1600536814003614/lh5693sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814003614/lh5693Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814003614/lh5693Isup3.cml
All chemicals used were purchased from commercial sources and used without further purification. Carbazole-9-acetaldehyde (2.09 g, 10 mmol) and 4-(methylsulfonyl)aniline (1.71 g, 10 mmol) were mixed in 1,2-dichloroethane (35 ml), followed by the addition of sodium triacetoxyborohydrate (2.97 g, 14 mmol). The reaction mixture was stirred at room temporature under a N2 atmosphere for 12 h and then quenched by aqueous saturated NaHCO3. The resulted mixture was extracted with EtOAc, dried (MgSO4) and concentrated to give the crude product as nearly colorless oil, which was further purified by
(Hexane/EtOAc 1/1) to provide white solid (2.89 g, 79%). This solid was characterized by NMR to be the title compound. Crystals were grown from MeOH/H2O (50:1 v/v) solution by slow evaporation.For the methyl group, the hydrogen atoms were added in calculated positions using a riding-model with C—H = 0.98 Å and U(H) = 1.5Ueq(C). The torsion angle, which defines the orientation of the methyl group about the C—S bond, was refined. The hydrogen atom bonded to N2 was refined isotropically. The rest of the hydrogen atoms were included in the model in calculated positions using a riding-model with C—H = 0.95 to 0.99 Å and U(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).C21H20N2O2S | F(000) = 768 |
Mr = 364.45 | Dx = 1.344 Mg m−3 |
Orthorhombic, Pna21 | Synchrotron radiation, λ = 0.7749 Å |
Hall symbol: P 2c -2n | Cell parameters from 5294 reflections |
a = 15.061 (3) Å | θ = 2.5–30.9° |
b = 21.992 (4) Å | µ = 0.21 mm−1 |
c = 5.437 (1) Å | T = 150 K |
V = 1800.9 (6) Å3 | Needle, colorless |
Z = 4 | 0.13 × 0.01 × 0.01 mm |
Bruker APEXII diffractometer | 4447 independent reflections |
Radiation source: synchrotron | 3950 reflections with I > 2σ(I) |
Si-<111> channel cut crystal monochromator | Rint = 0.094 |
ω scans | θmax = 31.1°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −20→19 |
Tmin = 0.635, Tmax = 0.746 | k = −29→29 |
21673 measured reflections | l = −7→7 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0448P)2 + 0.0604P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
4447 reflections | Δρmax = 0.21 e Å−3 |
240 parameters | Δρmin = −0.33 e Å−3 |
1 restraint | Absolute structure: Flack parameter determined using 1610 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 constraints | Absolute structure parameter: 0.04 (6) |
Primary atom site location: structure-invariant direct methods |
C21H20N2O2S | V = 1800.9 (6) Å3 |
Mr = 364.45 | Z = 4 |
Orthorhombic, Pna21 | Synchrotron radiation, λ = 0.7749 Å |
a = 15.061 (3) Å | µ = 0.21 mm−1 |
b = 21.992 (4) Å | T = 150 K |
c = 5.437 (1) Å | 0.13 × 0.01 × 0.01 mm |
Bruker APEXII diffractometer | 4447 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3950 reflections with I > 2σ(I) |
Tmin = 0.635, Tmax = 0.746 | Rint = 0.094 |
21673 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.118 | Δρmax = 0.21 e Å−3 |
S = 1.05 | Δρmin = −0.33 e Å−3 |
4447 reflections | Absolute structure: Flack parameter determined using 1610 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
240 parameters | Absolute structure parameter: 0.04 (6) |
1 restraint |
Experimental. Intensity data were collected at 150 K on a D8 goniostat equipped with a Bruker APEXII CCD detector at Beamline 11.3.1 at the Advanced Light Source (Lawrence Berkeley National Laboratory) using synchrotron radiation tuned to a wavelength of 0.7749 Angstroms. For data collection, frames were measured for a duration of 1 second using omega scans with a frame width of 0.3 degrees out to a maximum 2theta value of about 60 degrees. The data frames were collected using the program APEX2 and processed using the program SAINT within APEX2. The data were corrected for absorption and beam corrections based on the multi-scan technique as implemented in SADABS. |
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. For the methyl group, the hydrogen atoms were added at calculated positions using a riding model with U(H) = 1.5 * Ueq(bonded carbon atom). The torsion angle, which defines the orientation of the methyl group about the C-S bond, was refined. The hydrogen atom bonded to N(2) was refined isotropically. It is involved in an intermolecular hydrogen bond with atom O(2). The rest of the hydrogen atoms were included in the model at calculated positions using a riding model with U(H) = 1.2 * Ueq(bonded atom). |
x | y | z | Uiso*/Ueq | ||
C1 | 0.1214 (2) | 0.82284 (13) | 0.0581 (6) | 0.0327 (6) | |
C2 | 0.0477 (2) | 0.84713 (15) | 0.1764 (7) | 0.0399 (7) | |
H2 | 0.0219 | 0.8276 | 0.315 | 0.048* | |
C3 | 0.0132 (2) | 0.90105 (14) | 0.0840 (10) | 0.0506 (9) | |
H3 | −0.0374 | 0.9187 | 0.16 | 0.061* | |
C4 | 0.0514 (3) | 0.92970 (16) | −0.1175 (9) | 0.0539 (11) | |
H4 | 0.0268 | 0.9668 | −0.1755 | 0.065* | |
C5 | 0.1243 (3) | 0.90545 (16) | −0.2349 (8) | 0.0480 (10) | |
H5 | 0.1496 | 0.9255 | −0.3729 | 0.058* | |
C6 | 0.1607 (2) | 0.85076 (14) | −0.1479 (6) | 0.0360 (7) | |
C7 | 0.2347 (2) | 0.81324 (15) | −0.2213 (6) | 0.0354 (7) | |
C8 | 0.2982 (2) | 0.81655 (16) | −0.4086 (7) | 0.0440 (8) | |
H8 | 0.2967 | 0.849 | −0.5239 | 0.053* | |
C9 | 0.3627 (2) | 0.77243 (17) | −0.4247 (8) | 0.0502 (9) | |
H9 | 0.4059 | 0.7746 | −0.5516 | 0.06* | |
C10 | 0.3653 (2) | 0.72436 (18) | −0.2553 (8) | 0.0494 (9) | |
H10 | 0.4106 | 0.6945 | −0.2692 | 0.059* | |
C11 | 0.3031 (2) | 0.71940 (15) | −0.0676 (7) | 0.0404 (8) | |
H11 | 0.305 | 0.6869 | 0.0473 | 0.048* | |
C12 | 0.2379 (2) | 0.76431 (13) | −0.0553 (6) | 0.0317 (7) | |
C13 | 0.1389 (2) | 0.72389 (14) | 0.2840 (6) | 0.0328 (6) | |
H13A | 0.1136 | 0.7433 | 0.4327 | 0.039* | |
H13B | 0.1898 | 0.6984 | 0.3354 | 0.039* | |
C14 | 0.06868 (19) | 0.68418 (13) | 0.1617 (5) | 0.0269 (6) | |
H14A | 0.0188 | 0.7098 | 0.1041 | 0.032* | |
H14B | 0.0946 | 0.6633 | 0.0173 | 0.032* | |
C15 | −0.02888 (17) | 0.59855 (12) | 0.2799 (5) | 0.0221 (5) | |
C16 | −0.08094 (17) | 0.60306 (11) | 0.0661 (5) | 0.0255 (5) | |
H16 | −0.0722 | 0.636 | −0.0442 | 0.031* | |
C17 | −0.14500 (18) | 0.55956 (12) | 0.0158 (5) | 0.0246 (5) | |
H17 | −0.1804 | 0.5629 | −0.1283 | 0.03* | |
C18 | −0.15764 (17) | 0.51094 (13) | 0.1759 (5) | 0.0231 (5) | |
C19 | −0.10887 (18) | 0.50682 (12) | 0.3933 (5) | 0.0246 (5) | |
H19 | −0.1192 | 0.4743 | 0.5049 | 0.03* | |
C20 | −0.04564 (18) | 0.55020 (11) | 0.4450 (5) | 0.0235 (5) | |
H20 | −0.0128 | 0.5476 | 0.5938 | 0.028* | |
C21 | −0.32563 (18) | 0.46030 (14) | 0.2710 (6) | 0.0309 (6) | |
H21A | −0.3532 | 0.4995 | 0.2312 | 0.046* | |
H21B | −0.3106 | 0.4593 | 0.4463 | 0.046* | |
H21C | −0.3673 | 0.4273 | 0.2335 | 0.046* | |
N1 | 0.16909 (16) | 0.77046 (11) | 0.1140 (5) | 0.0316 (5) | |
N2 | 0.03638 (16) | 0.63949 (10) | 0.3373 (5) | 0.0266 (5) | |
H1N2 | 0.072 (2) | 0.6283 (16) | 0.458 (8) | 0.033 (9)* | |
O1 | −0.25201 (17) | 0.45669 (11) | −0.1613 (4) | 0.0384 (6) | |
O2 | −0.18686 (14) | 0.39497 (10) | 0.1746 (4) | 0.0342 (5) | |
S | −0.22847 (4) | 0.45106 (3) | 0.09511 (14) | 0.02501 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0351 (14) | 0.0268 (13) | 0.0363 (17) | −0.0085 (11) | −0.0104 (13) | 0.0006 (12) |
C2 | 0.0363 (16) | 0.0383 (17) | 0.0449 (18) | −0.0062 (13) | −0.0093 (14) | 0.0000 (15) |
C3 | 0.0440 (18) | 0.0332 (15) | 0.075 (3) | −0.0018 (13) | −0.020 (2) | −0.006 (2) |
C4 | 0.051 (2) | 0.0314 (16) | 0.079 (3) | −0.0054 (16) | −0.033 (2) | 0.0126 (19) |
C5 | 0.051 (2) | 0.0380 (17) | 0.055 (2) | −0.0196 (16) | −0.0268 (18) | 0.0199 (17) |
C6 | 0.0396 (16) | 0.0318 (14) | 0.0365 (16) | −0.0144 (13) | −0.0123 (13) | 0.0060 (13) |
C7 | 0.0398 (17) | 0.0363 (16) | 0.0300 (15) | −0.0186 (13) | −0.0082 (13) | 0.0045 (13) |
C8 | 0.0500 (18) | 0.0485 (18) | 0.0336 (15) | −0.0260 (15) | −0.0034 (18) | 0.0030 (18) |
C9 | 0.052 (2) | 0.055 (2) | 0.044 (2) | −0.0253 (16) | 0.0139 (19) | −0.010 (2) |
C10 | 0.0450 (19) | 0.046 (2) | 0.057 (2) | −0.0137 (16) | 0.0106 (18) | −0.0116 (18) |
C11 | 0.0416 (17) | 0.0318 (15) | 0.048 (2) | −0.0100 (14) | 0.0013 (16) | −0.0027 (14) |
C12 | 0.0352 (16) | 0.0296 (14) | 0.0303 (15) | −0.0144 (12) | −0.0021 (12) | 0.0013 (12) |
C13 | 0.0346 (15) | 0.0324 (14) | 0.0314 (15) | −0.0075 (12) | −0.0042 (13) | 0.0071 (12) |
C14 | 0.0296 (13) | 0.0272 (13) | 0.0240 (13) | −0.0030 (11) | −0.0001 (10) | 0.0033 (10) |
C15 | 0.0219 (12) | 0.0227 (12) | 0.0217 (12) | 0.0022 (10) | 0.0025 (10) | −0.0006 (10) |
C16 | 0.0274 (12) | 0.0248 (12) | 0.0244 (14) | 0.0007 (9) | 0.0009 (11) | 0.0049 (11) |
C17 | 0.0241 (12) | 0.0293 (13) | 0.0204 (12) | 0.0039 (10) | −0.0008 (10) | −0.0008 (10) |
C18 | 0.0221 (11) | 0.0255 (12) | 0.0217 (11) | 0.0003 (10) | 0.0032 (10) | −0.0012 (10) |
C19 | 0.0260 (12) | 0.0274 (13) | 0.0206 (12) | 0.0019 (11) | 0.0036 (10) | 0.0029 (10) |
C20 | 0.0232 (12) | 0.0276 (12) | 0.0198 (12) | 0.0021 (10) | −0.0014 (10) | 0.0015 (10) |
C21 | 0.0214 (12) | 0.0408 (16) | 0.0306 (14) | −0.0027 (12) | 0.0032 (11) | −0.0024 (13) |
N1 | 0.0343 (12) | 0.0285 (11) | 0.0320 (13) | −0.0062 (9) | −0.0019 (12) | 0.0060 (11) |
N2 | 0.0258 (11) | 0.0275 (11) | 0.0266 (12) | −0.0027 (9) | −0.0041 (10) | 0.0058 (10) |
O1 | 0.0463 (13) | 0.0475 (14) | 0.0214 (11) | −0.0148 (10) | −0.0013 (10) | −0.0018 (9) |
O2 | 0.0349 (11) | 0.0261 (10) | 0.0414 (12) | −0.0012 (8) | 0.0067 (9) | −0.0009 (8) |
S | 0.0255 (3) | 0.0285 (3) | 0.0210 (3) | −0.0031 (2) | 0.0026 (3) | −0.0023 (3) |
C1—C2 | 1.389 (5) | C13—H13A | 0.99 |
C1—N1 | 1.391 (4) | C13—H13B | 0.99 |
C1—C6 | 1.408 (5) | C14—N2 | 1.454 (4) |
C2—C3 | 1.388 (5) | C14—H14A | 0.99 |
C2—H2 | 0.95 | C14—H14B | 0.99 |
C3—C4 | 1.388 (7) | C15—N2 | 1.369 (4) |
C3—H3 | 0.95 | C15—C16 | 1.406 (4) |
C4—C5 | 1.377 (7) | C15—C20 | 1.414 (4) |
C4—H4 | 0.95 | C16—C17 | 1.386 (4) |
C5—C6 | 1.404 (5) | C16—H16 | 0.95 |
C5—H5 | 0.95 | C17—C18 | 1.392 (4) |
C6—C7 | 1.443 (5) | C17—H17 | 0.95 |
C7—C8 | 1.399 (5) | C18—C19 | 1.395 (4) |
C7—C12 | 1.405 (5) | C18—S | 1.751 (3) |
C8—C9 | 1.376 (5) | C19—C20 | 1.377 (4) |
C8—H8 | 0.95 | C19—H19 | 0.95 |
C9—C10 | 1.403 (6) | C20—H20 | 0.95 |
C9—H9 | 0.95 | C21—S | 1.760 (3) |
C10—C11 | 1.389 (5) | C21—H21A | 0.98 |
C10—H10 | 0.95 | C21—H21B | 0.98 |
C11—C12 | 1.394 (5) | C21—H21C | 0.98 |
C11—H11 | 0.95 | N2—H1N2 | 0.88 (4) |
C12—N1 | 1.393 (4) | O1—S | 1.444 (2) |
C13—N1 | 1.453 (4) | O2—S | 1.449 (2) |
C13—C14 | 1.524 (4) | ||
C2—C1—N1 | 129.0 (3) | N2—C14—C13 | 109.4 (2) |
C2—C1—C6 | 122.5 (3) | N2—C14—H14A | 109.8 |
N1—C1—C6 | 108.5 (3) | C13—C14—H14A | 109.8 |
C3—C2—C1 | 117.4 (4) | N2—C14—H14B | 109.8 |
C3—C2—H2 | 121.3 | C13—C14—H14B | 109.8 |
C1—C2—H2 | 121.3 | H14A—C14—H14B | 108.2 |
C4—C3—C2 | 121.2 (4) | N2—C15—C16 | 122.8 (2) |
C4—C3—H3 | 119.4 | N2—C15—C20 | 118.6 (2) |
C2—C3—H3 | 119.4 | C16—C15—C20 | 118.6 (2) |
C5—C4—C3 | 121.3 (3) | C17—C16—C15 | 120.2 (2) |
C5—C4—H4 | 119.3 | C17—C16—H16 | 119.9 |
C3—C4—H4 | 119.3 | C15—C16—H16 | 119.9 |
C4—C5—C6 | 119.1 (4) | C16—C17—C18 | 120.1 (3) |
C4—C5—H5 | 120.4 | C16—C17—H17 | 119.9 |
C6—C5—H5 | 120.4 | C18—C17—H17 | 119.9 |
C5—C6—C1 | 118.5 (4) | C17—C18—C19 | 120.5 (3) |
C5—C6—C7 | 134.3 (4) | C17—C18—S | 120.3 (2) |
C1—C6—C7 | 107.2 (3) | C19—C18—S | 119.0 (2) |
C8—C7—C12 | 119.0 (3) | C20—C19—C18 | 119.5 (2) |
C8—C7—C6 | 134.4 (3) | C20—C19—H19 | 120.3 |
C12—C7—C6 | 106.6 (3) | C18—C19—H19 | 120.3 |
C9—C8—C7 | 119.5 (3) | C19—C20—C15 | 121.0 (3) |
C9—C8—H8 | 120.3 | C19—C20—H20 | 119.5 |
C7—C8—H8 | 120.3 | C15—C20—H20 | 119.5 |
C8—C9—C10 | 120.6 (4) | S—C21—H21A | 109.5 |
C8—C9—H9 | 119.7 | S—C21—H21B | 109.5 |
C10—C9—H9 | 119.7 | H21A—C21—H21B | 109.5 |
C11—C10—C9 | 121.5 (4) | S—C21—H21C | 109.5 |
C11—C10—H10 | 119.2 | H21A—C21—H21C | 109.5 |
C9—C10—H10 | 119.2 | H21B—C21—H21C | 109.5 |
C10—C11—C12 | 117.0 (3) | C1—N1—C12 | 108.7 (3) |
C10—C11—H11 | 121.5 | C1—N1—C13 | 124.1 (3) |
C12—C11—H11 | 121.5 | C12—N1—C13 | 125.8 (3) |
N1—C12—C11 | 128.6 (3) | C15—N2—C14 | 122.4 (2) |
N1—C12—C7 | 108.9 (3) | C15—N2—H1N2 | 115 (2) |
C11—C12—C7 | 122.4 (3) | C14—N2—H1N2 | 118 (2) |
N1—C13—C14 | 110.1 (3) | O1—S—O2 | 117.85 (15) |
N1—C13—H13A | 109.6 | O1—S—C18 | 109.12 (14) |
C14—C13—H13A | 109.6 | O2—S—C18 | 107.56 (13) |
N1—C13—H13B | 109.6 | O1—S—C21 | 108.10 (16) |
C14—C13—H13B | 109.6 | O2—S—C21 | 107.20 (14) |
H13A—C13—H13B | 108.2 | C18—S—C21 | 106.46 (14) |
N1—C1—C2—C3 | 179.1 (3) | C20—C15—C16—C17 | −2.3 (4) |
C6—C1—C2—C3 | −0.1 (5) | C15—C16—C17—C18 | −0.5 (4) |
C1—C2—C3—C4 | −0.5 (5) | C16—C17—C18—C19 | 2.8 (4) |
C2—C3—C4—C5 | 0.7 (6) | C16—C17—C18—S | −172.1 (2) |
C3—C4—C5—C6 | −0.2 (5) | C17—C18—C19—C20 | −2.2 (4) |
C4—C5—C6—C1 | −0.4 (5) | S—C18—C19—C20 | 172.7 (2) |
C4—C5—C6—C7 | −179.7 (3) | C18—C19—C20—C15 | −0.6 (4) |
C2—C1—C6—C5 | 0.5 (4) | N2—C15—C20—C19 | −178.3 (2) |
N1—C1—C6—C5 | −178.8 (3) | C16—C15—C20—C19 | 2.8 (4) |
C2—C1—C6—C7 | −180.0 (3) | C2—C1—N1—C12 | −179.9 (3) |
N1—C1—C6—C7 | 0.7 (3) | C6—C1—N1—C12 | −0.6 (3) |
C5—C6—C7—C8 | −0.7 (6) | C2—C1—N1—C13 | 12.9 (5) |
C1—C6—C7—C8 | 179.9 (3) | C6—C1—N1—C13 | −167.8 (3) |
C5—C6—C7—C12 | 178.8 (3) | C11—C12—N1—C1 | 178.7 (3) |
C1—C6—C7—C12 | −0.6 (3) | C7—C12—N1—C1 | 0.2 (3) |
C12—C7—C8—C9 | −0.8 (5) | C11—C12—N1—C13 | −14.3 (5) |
C6—C7—C8—C9 | 178.7 (4) | C7—C12—N1—C13 | 167.2 (3) |
C7—C8—C9—C10 | 0.0 (5) | C14—C13—N1—C1 | 77.2 (4) |
C8—C9—C10—C11 | 0.3 (6) | C14—C13—N1—C12 | −87.8 (3) |
C9—C10—C11—C12 | 0.1 (5) | C16—C15—N2—C14 | −11.9 (4) |
C10—C11—C12—N1 | −179.2 (3) | C20—C15—N2—C14 | 169.2 (2) |
C10—C11—C12—C7 | −0.9 (5) | C13—C14—N2—C15 | 178.3 (2) |
C8—C7—C12—N1 | 179.9 (3) | C17—C18—S—O1 | 10.9 (3) |
C6—C7—C12—N1 | 0.2 (3) | C19—C18—S—O1 | −164.0 (2) |
C8—C7—C12—C11 | 1.2 (5) | C17—C18—S—O2 | 139.8 (2) |
C6—C7—C12—C11 | −178.4 (3) | C19—C18—S—O2 | −35.1 (2) |
N1—C13—C14—N2 | −177.6 (2) | C17—C18—S—C21 | −105.5 (2) |
N2—C15—C16—C17 | 178.8 (3) | C19—C18—S—C21 | 79.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O2i | 0.88 (4) | 2.16 (4) | 3.012 (3) | 164 (3) |
C21—H21B···O1ii | 0.98 | 2.31 | 3.281 (4) | 171 |
Symmetry codes: (i) −x, −y+1, z+1/2; (ii) x, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O2i | 0.88 (4) | 2.16 (4) | 3.012 (3) | 164 (3) |
C21—H21B···O1ii | 0.98 | 2.31 | 3.281 (4) | 170.9 |
Symmetry codes: (i) −x, −y+1, z+1/2; (ii) x, y, z+1. |
Acknowledgements
Crystallographic data were collected through the SCrALS (Service Crystallography at Advanced Light Source) program at the Small-Crystal Crystallography Beamline 11.3.1 at the Advanced Light Source (ALS), Lawrence Berkeley National Laboratory. The ALS is supported by the US Department of Energy, Office of Energy Sciences Materials Sciences Division, under contract DE—AC02–05CH11231. We thank Dr Jeanette Krause of the University of Cincinnati and Dr Allen G. Oliver of the University of Notre Dame for the data collection.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Carbazole based compounds are important in drug discovery. As part of our ongoing effort to develop bioactive carbazole compounds (Lai et al., 2014), herein we report the crystal structure of the title compound (I). Compound (I) was obtained by reductive amination of carbazole-9-acetaldehyde through a direct procedure from Abdel-Magid et al. (1996). Carbazole-9-acetaldehyde was synthesized according to the method of Hallberg et al. (1982). The molecular structure of (I) is shown in Fig.1. A portion of the unit cell shown in Fig. 2 illustrates how the molecules are linked by strong intermolecular N—H···O hydrogen bonds. These hydrogen bonds form a one-dimensional chain along [0 0 1] with a graph set descriptor of C(8) (Bernstein et al., 1995).