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There are two independent mol­ecules in the asymmetric unit of the title compound, C11H12N2O2, which differ in the conformation of the propyl substituent. N—H...O, C—H...O and π–π interactions between inversion-related mol­ecules result in a supramolecular assembly.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804003393/ci6338sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804003393/ci6338Isup2.hkl
Contains datablock I

CCDC reference: 236093

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.052
  • wR factor = 0.142
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.680 1.000 Tmin' and Tmax expected: 0.964 0.982 RR' = 0.693 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.69
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT230_ALERT_2_C Hirshfeld Test Diff for O1A - N2A = 5.69 su PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.14 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

6-Nitro-2-propyl-1H-indole top
Crystal data top
C11H12N2O2Z = 4
Mr = 204.23F(000) = 432
Triclinic, P1Dx = 1.300 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.229 (2) ÅCell parameters from 1705 reflections
b = 11.828 (3) Åθ = 2.8–27.4°
c = 12.088 (3) ŵ = 0.09 mm1
α = 67.403 (4)°T = 100 K
β = 86.940 (4)°Block, light yellow
γ = 74.256 (4)°0.40 × 0.25 × 0.20 mm
V = 1043.8 (5) Å3
Data collection top
Bruker CCD area-detector
diffractometer
3980 independent reflections
Radiation source: fine-focus sealed tube2616 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 810
Tmin = 0.68, Tmax = 1.00k = 1414
7051 measured reflectionsl = 1414
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0899P)2]
where P = (Fo2 + 2Fc2)/3
3980 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.33 e Å3
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 20 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Coverage of the unique set is over 99% complete. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.7952 (2)0.53774 (17)0.20466 (14)0.0299 (4)
O2A0.9550 (2)0.44383 (16)0.36947 (15)0.0293 (4)
N1A0.5920 (2)0.60278 (17)0.66399 (16)0.0204 (5)
H1AA0.67510.56010.71950.025*
N2A0.8216 (3)0.51688 (19)0.31127 (18)0.0232 (5)
C2A0.4358 (3)0.6727 (2)0.6803 (2)0.0202 (5)
C3A0.3401 (3)0.7278 (2)0.5730 (2)0.0214 (5)
H3AA0.22810.78200.55900.026*
C4A0.4395 (3)0.6887 (2)0.48718 (19)0.0193 (5)
C5A0.4113 (3)0.7095 (2)0.3666 (2)0.0218 (5)
H5AA0.30560.76080.32510.026*
C6A0.5387 (3)0.6547 (2)0.3089 (2)0.0218 (5)
H6AA0.52260.66900.22680.026*
C7A0.6922 (3)0.5775 (2)0.3732 (2)0.0205 (5)
C8A0.7267 (3)0.5524 (2)0.4919 (2)0.0204 (5)
H8AA0.83190.49920.53300.024*
C9A0.5978 (3)0.6100 (2)0.54776 (19)0.0185 (5)
C10A0.3895 (3)0.6800 (2)0.7988 (2)0.0230 (5)
H10A0.38850.59410.85660.028*
H10B0.27340.73640.79010.028*
C11A0.5075 (3)0.7291 (2)0.8505 (2)0.0257 (6)
H11A0.51390.81300.79120.031*
H11B0.62240.66990.86460.031*
C12A0.4493 (3)0.7423 (3)0.9680 (2)0.0328 (6)
H12A0.52900.77400.99760.049*
H12B0.44500.65911.02770.049*
H12C0.33650.80230.95430.049*
O1B1.0916 (2)0.67913 (17)1.20003 (15)0.0374 (5)
O2B1.1694 (2)0.53805 (16)1.12174 (15)0.0288 (4)
N1B0.8769 (2)0.77012 (18)0.70143 (16)0.0204 (5)
H1BA0.92190.70210.68530.024*
N2B1.0889 (3)0.6451 (2)1.11582 (17)0.0243 (5)
C2B0.7741 (3)0.8825 (2)0.6231 (2)0.0213 (5)
C3B0.7285 (3)0.9665 (2)0.6784 (2)0.0239 (6)
H3BA0.65771.05100.64410.029*
C4B0.8061 (3)0.9048 (2)0.7970 (2)0.0225 (5)
C5B0.8084 (3)0.9404 (2)0.8949 (2)0.0282 (6)
H5BA0.74701.02320.88920.034*
C6B0.9000 (3)0.8548 (2)0.9991 (2)0.0279 (6)
H6BA0.90280.87831.06560.033*
C7B0.9894 (3)0.7325 (2)1.0066 (2)0.0222 (5)
C8B0.9894 (3)0.6920 (2)0.9134 (2)0.0212 (5)
H8BA1.04850.60820.92090.025*
C9B0.8986 (3)0.7802 (2)0.80899 (19)0.0181 (5)
C10B0.7279 (3)0.9004 (2)0.4985 (2)0.0250 (6)
H10C0.64790.98560.45920.030*
H10D0.66890.83630.50280.030*
C11B0.8803 (3)0.8883 (3)0.4209 (2)0.0324 (6)
H11C0.94330.94920.41960.039*
H11D0.95730.80140.45700.039*
C12B0.8263 (4)0.9146 (3)0.2925 (2)0.0402 (7)
H12D0.92650.90620.24570.060*
H12E0.75161.00120.25600.060*
H12F0.76590.85340.29340.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0259 (10)0.0474 (11)0.0251 (10)0.0164 (9)0.0068 (8)0.0194 (8)
O2A0.0183 (10)0.0378 (10)0.0366 (10)0.0064 (8)0.0016 (8)0.0201 (8)
N1A0.0122 (10)0.0262 (11)0.0224 (10)0.0051 (9)0.0018 (8)0.0086 (8)
N2A0.0129 (11)0.0294 (11)0.0316 (12)0.0101 (9)0.0041 (9)0.0135 (9)
C2A0.0115 (12)0.0248 (12)0.0266 (12)0.0084 (10)0.0012 (9)0.0101 (10)
C3A0.0119 (12)0.0261 (13)0.0278 (13)0.0064 (10)0.0014 (10)0.0110 (11)
C4A0.0160 (12)0.0204 (12)0.0223 (12)0.0082 (10)0.0012 (9)0.0067 (10)
C5A0.0172 (13)0.0233 (12)0.0244 (12)0.0064 (10)0.0030 (10)0.0074 (10)
C6A0.0224 (14)0.0254 (13)0.0195 (12)0.0111 (11)0.0009 (10)0.0075 (10)
C7A0.0188 (13)0.0226 (12)0.0243 (12)0.0091 (10)0.0046 (10)0.0115 (10)
C8A0.0144 (12)0.0249 (12)0.0246 (12)0.0089 (10)0.0007 (9)0.0100 (10)
C9A0.0137 (12)0.0218 (12)0.0229 (12)0.0095 (10)0.0017 (9)0.0082 (10)
C10A0.0142 (12)0.0335 (14)0.0271 (13)0.0113 (11)0.0037 (10)0.0149 (11)
C11A0.0166 (13)0.0386 (15)0.0283 (13)0.0128 (11)0.0031 (10)0.0164 (11)
C12A0.0277 (15)0.0489 (17)0.0300 (14)0.0184 (13)0.0045 (11)0.0189 (13)
O1B0.0387 (12)0.0468 (12)0.0291 (10)0.0088 (10)0.0047 (8)0.0182 (9)
O2B0.0175 (9)0.0340 (10)0.0320 (10)0.0038 (8)0.0044 (7)0.0110 (8)
N1B0.0132 (10)0.0269 (11)0.0241 (10)0.0074 (8)0.0022 (8)0.0119 (9)
N2B0.0141 (11)0.0356 (12)0.0260 (11)0.0108 (9)0.0012 (8)0.0121 (10)
C2B0.0145 (12)0.0254 (12)0.0219 (12)0.0096 (10)0.0008 (9)0.0041 (10)
C3B0.0191 (13)0.0233 (12)0.0260 (13)0.0060 (10)0.0016 (10)0.0055 (10)
C4B0.0184 (13)0.0256 (12)0.0237 (12)0.0081 (10)0.0014 (10)0.0081 (10)
C5B0.0281 (15)0.0284 (13)0.0299 (14)0.0060 (11)0.0013 (11)0.0141 (11)
C6B0.0311 (15)0.0314 (14)0.0239 (13)0.0090 (12)0.0004 (11)0.0131 (11)
C7B0.0149 (12)0.0286 (13)0.0205 (12)0.0072 (10)0.0010 (9)0.0057 (10)
C8B0.0118 (12)0.0255 (13)0.0267 (13)0.0076 (10)0.0039 (10)0.0093 (10)
C9B0.0106 (12)0.0262 (12)0.0195 (11)0.0096 (10)0.0033 (9)0.0081 (10)
C10B0.0181 (13)0.0323 (14)0.0247 (13)0.0107 (11)0.0014 (10)0.0086 (11)
C11B0.0191 (14)0.0540 (18)0.0288 (14)0.0114 (13)0.0029 (11)0.0204 (13)
C12B0.0390 (18)0.0568 (19)0.0261 (14)0.0099 (15)0.0023 (12)0.0196 (13)
Geometric parameters (Å, º) top
O1A—N2A1.235 (2)O1B—N2B1.233 (2)
O2A—N2A1.244 (3)O2B—N2B1.236 (2)
N1A—C9A1.374 (3)N1B—C2B1.374 (3)
N1A—C2A1.377 (3)N1B—C9B1.376 (3)
N1A—H1AA0.88N1B—H1BA0.88
N2A—C7A1.457 (3)N2B—C7B1.446 (3)
C2A—C3A1.381 (3)C2B—C3B1.362 (3)
C2A—C10A1.491 (3)C2B—C10B1.493 (3)
C3A—C4A1.425 (3)C3B—C4B1.427 (3)
C3A—H3AA0.95C3B—H3BA0.95
C4A—C5A1.403 (3)C4B—C5B1.402 (3)
C4A—C9A1.421 (3)C4B—C9B1.418 (3)
C5A—C6A1.381 (3)C5B—C6B1.373 (4)
C5A—H5AA0.95C5B—H5BA0.95
C6A—C7A1.403 (3)C6B—C7B1.405 (3)
C6A—H6AA0.95C6B—H6BA0.95
C7A—C8A1.378 (3)C7B—C8B1.382 (3)
C8A—C9A1.389 (3)C8B—C9B1.381 (3)
C8A—H8AA0.95C8B—H8BA0.95
C10A—C11A1.523 (3)C10B—C11B1.535 (3)
C10A—H10A0.99C10B—H10C0.99
C10A—H10B0.99C10B—H10D0.99
C11A—C12A1.526 (3)C11B—C12B1.527 (4)
C11A—H11A0.99C11B—H11C0.99
C11A—H11B0.99C11B—H11D0.99
C12A—H12A0.98C12B—H12D0.98
C12A—H12B0.98C12B—H12E0.98
C12A—H12C0.98C12B—H12F0.98
C9A—N1A—C2A109.5 (2)C2B—N1B—C9B109.59 (19)
C9A—N1A—H1AA125.3C2B—N1B—H1BA125.2
C2A—N1A—H1AA125.3C9B—N1B—H1BA125.2
O1A—N2A—O2A122.39 (19)O1B—N2B—O2B121.9 (2)
O1A—N2A—C7A119.6 (2)O1B—N2B—C7B119.4 (2)
O2A—N2A—C7A118.0 (2)O2B—N2B—C7B118.66 (19)
N1A—C2A—C3A108.7 (2)C3B—C2B—N1B109.0 (2)
N1A—C2A—C10A122.0 (2)C3B—C2B—C10B129.1 (2)
C3A—C2A—C10A129.4 (2)N1B—C2B—C10B121.9 (2)
C2A—C3A—C4A107.8 (2)C2B—C3B—C4B107.8 (2)
C2A—C3A—H3AA126.1C2B—C3B—H3BA126.1
C4A—C3A—H3AA126.1C4B—C3B—H3BA126.1
C5A—C4A—C9A119.2 (2)C5B—C4B—C9B118.7 (2)
C5A—C4A—C3A134.5 (2)C5B—C4B—C3B134.9 (2)
C9A—C4A—C3A106.3 (2)C9B—C4B—C3B106.5 (2)
C6A—C5A—C4A119.4 (2)C6B—C5B—C4B119.6 (2)
C6A—C5A—H5AA120.3C6B—C5B—H5BA120.2
C4A—C5A—H5AA120.3C4B—C5B—H5BA120.2
C5A—C6A—C7A119.0 (2)C5B—C6B—C7B119.6 (2)
C5A—C6A—H6AA120.5C5B—C6B—H6BA120.2
C7A—C6A—H6AA120.5C7B—C6B—H6BA120.2
C8A—C7A—C6A124.3 (2)C8B—C7B—C6B123.1 (2)
C8A—C7A—N2A117.9 (2)C8B—C7B—N2B118.2 (2)
C6A—C7A—N2A117.7 (2)C6B—C7B—N2B118.7 (2)
C7A—C8A—C9A115.7 (2)C9B—C8B—C7B116.3 (2)
C7A—C8A—H8AA122.1C9B—C8B—H8BA121.9
C9A—C8A—H8AA122.1C7B—C8B—H8BA121.9
N1A—C9A—C8A129.8 (2)N1B—C9B—C8B130.1 (2)
N1A—C9A—C4A107.78 (19)N1B—C9B—C4B107.1 (2)
C8A—C9A—C4A122.4 (2)C8B—C9B—C4B122.8 (2)
C2A—C10A—C11A114.47 (19)C2B—C10B—C11B113.6 (2)
C2A—C10A—H10A108.6C2B—C10B—H10C108.9
C11A—C10A—H10A108.6C11B—C10B—H10C108.9
C2A—C10A—H10B108.6C2B—C10B—H10D108.9
C11A—C10A—H10B108.6C11B—C10B—H10D108.9
H10A—C10A—H10B107.6H10C—C10B—H10D107.7
C10A—C11A—C12A112.6 (2)C12B—C11B—C10B111.7 (2)
C10A—C11A—H11A109.1C12B—C11B—H11C109.3
C12A—C11A—H11A109.1C10B—C11B—H11C109.3
C10A—C11A—H11B109.1C12B—C11B—H11D109.3
C12A—C11A—H11B109.1C10B—C11B—H11D109.3
H11A—C11A—H11B107.8H11C—C11B—H11D107.9
C11A—C12A—H12A109.5C11B—C12B—H12D109.5
C11A—C12A—H12B109.5C11B—C12B—H12E109.5
H12A—C12A—H12B109.5H12D—C12B—H12E109.5
C11A—C12A—H12C109.5C11B—C12B—H12F109.5
H12A—C12A—H12C109.5H12D—C12B—H12F109.5
H12B—C12A—H12C109.5H12E—C12B—H12F109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···O2Bi0.882.102.965 (3)167
N1B—H1BA···O2Aii0.882.072.948 (3)173
C8A—H8AA···O2Aii0.952.533.203 (3)128
C11A—H11B···O2Bi0.992.543.448 (3)153
C10B—H10D···Cg10.992.783.726 (3)161
C11A—H11A···Cg20.992.723.346 (3)121
Symmetry codes: (i) x+2, y+1, z+2; (ii) x+2, y+1, z+1.
 

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