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The title compound, C15H13N3O4, crystallizes in the triclinic space group P\overline 1. The 6-nitro and methyl groups are essentially planar with the carbazole moiety, while the 1-nitro group is twisted out of the carbazole plane. Two neighboring mol­ecules are associated with each other through one benzene ring, indicating a weak π–π interaction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020574/hg6074sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020574/hg6074Isup2.hkl
Contains datablock I

CCDC reference: 251749

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.042
  • wR factor = 0.116
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C RADNW01_ALERT_1_C The radiation wavelength lies outside the expected range for the supplied radiation type. Expected range 0.71065-0.71075 Wavelength given = 0.70930 PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C1 .. 5.27 su
Alert level G RADNW01_ALERT_1_G The radiation wavelength given implies that Mo Kalpha1 has been used. Please check that this is correct. Wavelength given = 0.70930
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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

Computing details top

Data collection: CAD-4 PC Software (Enraf–Nonius, 1993); cell refinement: CAD-4 PC Software; data reduction: DATRD2 in NRCVAX (Gabe et al., 1989); program(s) used to solve structure: NRCVAX SOLVER; program(s) used to refine structure: NRCVAX LSTSQ and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) in NRCVAX; software used to prepare material for publication: SHELXL97.

9-Ethyl-3-methyl-1,6-dinitro-9H-carbazole top
Crystal data top
C15H13N3O4F(000) = 312
Mr = 299.28? #Insert any comments here.
Triclinic, P1Dx = 1.442 Mg m3
Hall symbol: -P 1Melting point: 429 K
a = 6.7094 (4) ÅMo Kα radiation, λ = 0.70930 Å
b = 8.8147 (6) ÅCell parameters from 25 reflections
c = 12.2004 (9) Åθ = 6.1–14.0°
α = 72.908 (6)°µ = 0.11 mm1
β = 87.720 (6)°T = 293 K
γ = 88.718 (6)°Needle, yellow
V = 689.09 (8) Å30.51 × 0.20 × 0.12 mm
Z = 2
Data collection top
Nonius CAD-4
diffractometer
Rint = 0.007
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.7°
Graphite monochromatorh = 77
ω scansk = 010
2698 measured reflectionsl = 1314
2442 independent reflections3 standard reflections every 120 min
1692 reflections with Inet > 2σ(Inet) intensity decay: 1.2%
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0515P)2 + 0.1899P]
where P = (Fo2 + 2Fc2)/3
2442 reflections(Δ/σ)max = 0.001
200 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.17 e Å3
Special details top

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.

TABLE of LEAST SQUARES PLANES

——- Plane No. 1 ———

Equation of the plane: 3.4329 (15)X + 4.087 (4)Y + 10.3793 (21)Z = 3.4664 (9)

Distances(A) to the plane from the atoms in the plane. N9 - 0.0091 (18) C1 0.0074 (22) C2 - 0.0407 (24) C3 - 0.0330 (24) C4 0.0069 (22) C4a 0.0339 (20) C4b 0.0332 (19) C5 0.0122 (22) C6 - 0.0266 (22) C7 - 0.0258 (23) C8 - 0.0083 (22) C8a 0.0118 (20) C9a 0.0220 (21)

Chi squared for this plane 1568.151

Distances(A) to the plane from the atoms out of the plane. N1 0.1750 (24) N6 - 0.0950 (25) C10 - 0.279 (3) C12 - 0.027 (3)

——- Plane No. 2 ———

Equation of the plane: 5.368 (12)X - 0.713 (24)Y + 6.931 (16)Z = 4.078 (13)

Distances(A) to the plane from the atoms in the plane. N1 0.000 (3) O1a 0.0000 (22) O1b 0.0000 (22)

——- Plane No. 3 ———

Equation of the plane: 3.472 (17)X + 3.382 (17)Y + 10.562 (21)Z = 3.633 (21)

Distances(A) to the plane from the atoms in the plane. N6 0.000 (3) O6a 0.0000 (23) O6b 0.0000 (23)

——- Plane No. 4 ———

Equation of the plane: 6.336 (7)X - 0.662 (11)Y - 3.55 (4)Z = 1.026 (10)

Distances(A) to the plane from the atoms in the plane. N9 0.0000 (22) C10 0.000 (3) C11 0.000 (4)

———————————————————————- Dihedral angle between planes A and B

A B Angle(°) 1 2 37.24 (9) 1 3 5.27 (15) 1 4 77.86 (17) 2 3 33.58 (10) 2 4 54.63 (23) 3 4 77.85 (25)

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*/UeqOcc. (<1)
O1A0.6810 (3)0.2723 (2)0.08878 (15)0.0680 (5)
O1B0.8095 (3)0.1447 (2)0.02367 (16)0.0776 (6)
O6A0.4115 (3)0.1958 (2)0.54203 (16)0.0796 (6)
O6B0.2239 (3)0.3960 (2)0.54437 (17)0.0837 (6)
N10.7038 (3)0.1512 (3)0.05920 (16)0.0542 (5)
N60.2610 (3)0.2535 (2)0.51102 (16)0.0557 (5)
N90.2828 (3)0.11477 (19)0.19406 (14)0.0431 (4)
C10.6113 (3)0.0053 (2)0.13046 (17)0.0441 (5)
C20.7224 (3)0.1326 (3)0.14370 (19)0.0503 (6)
H20.84010.12860.10000.060*
C30.6650 (3)0.2765 (3)0.2196 (2)0.0495 (6)
C40.4884 (3)0.2814 (2)0.28391 (19)0.0463 (5)
H40.44720.37640.33600.056*
C4A0.3738 (3)0.1452 (2)0.27068 (17)0.0406 (5)
C4B0.1846 (3)0.1191 (2)0.32324 (17)0.0400 (5)
C50.0552 (3)0.2172 (2)0.40242 (17)0.0430 (5)
H50.08530.32400.43550.052*
C60.1196 (3)0.1510 (2)0.43046 (17)0.0435 (5)
C70.1698 (3)0.0091 (3)0.38410 (18)0.0467 (5)
H70.28880.04910.40670.056*
C80.0423 (3)0.1072 (2)0.30493 (18)0.0463 (5)
H80.07340.21410.27300.056*
C8A0.1347 (3)0.0423 (2)0.27372 (17)0.0409 (5)
C9A0.4304 (3)0.0021 (2)0.19297 (17)0.0409 (5)
C100.2544 (4)0.2749 (3)0.1143 (2)0.0551 (6)
H10A0.11790.28640.08950.066*
H10B0.34150.28680.04700.066*
C110.2973 (4)0.4046 (3)0.1671 (2)0.0719 (8)
H11A0.27520.50610.11210.108*
H11B0.43350.39610.18960.108*
H11C0.21040.39430.23330.108*
C120.7964 (4)0.4229 (3)0.2344 (2)0.0685 (7)
H12A0.73460.51160.28980.103*0.50
H12B0.92410.40430.26060.103*0.50
H12C0.81370.44550.16230.103*0.50
H12D0.91360.39600.18530.103*0.50
H12E0.72420.50330.21450.103*0.50
H12F0.83460.46210.31280.103*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0670 (12)0.0528 (10)0.0792 (12)0.0106 (9)0.0062 (9)0.0119 (9)
O1B0.0636 (12)0.0942 (14)0.0665 (11)0.0116 (10)0.0259 (10)0.0130 (10)
O6A0.0573 (12)0.0864 (13)0.0840 (13)0.0101 (10)0.0310 (10)0.0129 (10)
O6B0.0825 (14)0.0548 (11)0.0975 (15)0.0010 (10)0.0400 (11)0.0026 (10)
N10.0390 (11)0.0673 (14)0.0512 (11)0.0076 (10)0.0029 (9)0.0096 (10)
N60.0489 (13)0.0616 (13)0.0530 (11)0.0010 (10)0.0117 (10)0.0128 (10)
N90.0395 (10)0.0387 (9)0.0477 (10)0.0008 (8)0.0031 (8)0.0079 (8)
C10.0372 (12)0.0493 (13)0.0455 (12)0.0075 (10)0.0030 (10)0.0137 (10)
C20.0371 (12)0.0624 (15)0.0570 (14)0.0021 (11)0.0050 (10)0.0271 (12)
C30.0394 (13)0.0525 (13)0.0628 (14)0.0037 (10)0.0015 (11)0.0269 (11)
C40.0419 (13)0.0413 (12)0.0566 (13)0.0004 (10)0.0015 (11)0.0161 (10)
C4A0.0361 (11)0.0402 (11)0.0468 (12)0.0013 (9)0.0010 (9)0.0150 (9)
C4B0.0362 (12)0.0406 (11)0.0434 (11)0.0002 (9)0.0012 (9)0.0130 (9)
C50.0429 (13)0.0390 (12)0.0457 (12)0.0005 (10)0.0018 (10)0.0107 (9)
C60.0383 (12)0.0484 (12)0.0429 (11)0.0014 (10)0.0048 (9)0.0128 (10)
C70.0364 (12)0.0545 (13)0.0510 (12)0.0059 (10)0.0012 (10)0.0192 (10)
C80.0444 (13)0.0401 (12)0.0545 (13)0.0069 (10)0.0026 (10)0.0142 (10)
C8A0.0365 (12)0.0423 (11)0.0449 (12)0.0003 (9)0.0016 (9)0.0142 (9)
C9A0.0366 (12)0.0446 (12)0.0435 (11)0.0011 (9)0.0016 (9)0.0157 (9)
C100.0476 (14)0.0520 (14)0.0573 (14)0.0011 (11)0.0003 (11)0.0035 (11)
C110.0808 (19)0.0473 (14)0.0827 (19)0.0008 (13)0.0083 (15)0.0131 (13)
C120.0522 (15)0.0608 (16)0.099 (2)0.0120 (12)0.0028 (14)0.0350 (15)
Geometric parameters (Å, º) top
O1A—N11.228 (2)C4B—C8A1.411 (3)
O1B—N11.226 (2)C5—C61.374 (3)
O6A—N61.217 (2)C5—H50.9300
O6B—N61.224 (2)C6—C71.396 (3)
N1—C11.460 (3)C7—C81.374 (3)
N6—C61.458 (3)C7—H70.9300
N9—C8A1.388 (3)C8—C8A1.395 (3)
N9—C9A1.390 (3)C8—H80.9300
N9—C101.473 (3)C10—C111.505 (3)
C1—C21.384 (3)C10—H10A0.9700
C1—C9A1.404 (3)C10—H10B0.9700
C2—C31.385 (3)C11—H11A0.9600
C2—H20.9300C11—H11B0.9600
C3—C41.389 (3)C11—H11C0.9600
C3—C121.516 (3)C12—H12A0.9600
C4—C4A1.383 (3)C12—H12B0.9600
C4—H40.9300C12—H12C0.9600
C4A—C9A1.414 (3)C12—H12D0.9600
C4A—C4B1.444 (3)C12—H12E0.9600
C4B—C51.382 (3)C12—H12F0.9600
O1B—N1—O1A123.2 (2)N9—C8A—C8129.08 (19)
O1B—N1—C1118.3 (2)N9—C8A—C4B109.70 (17)
O1A—N1—C1118.41 (19)C8—C8A—C4B121.21 (19)
O6A—N6—O6B122.3 (2)N9—C9A—C1133.76 (19)
O6A—N6—C6119.5 (2)N9—C9A—C4A109.20 (17)
O6B—N6—C6118.22 (18)C1—C9A—C4A117.00 (19)
C8A—N9—C9A108.03 (16)N9—C10—C11112.8 (2)
C8A—N9—C10121.53 (17)N9—C10—H10A109.0
C9A—N9—C10129.51 (18)C11—C10—H10A109.0
C2—C1—C9A120.07 (19)N9—C10—H10B109.0
C2—C1—N1116.07 (19)C11—C10—H10B109.0
C9A—C1—N1123.54 (19)H10A—C10—H10B107.8
C1—C2—C3122.4 (2)C10—C11—H11A109.5
C1—C2—H2118.8C10—C11—H11B109.5
C3—C2—H2118.8H11A—C11—H11B109.5
C2—C3—C4118.3 (2)C10—C11—H11C109.5
C2—C3—C12120.4 (2)H11A—C11—H11C109.5
C4—C3—C12121.3 (2)H11B—C11—H11C109.5
C4A—C4—C3120.1 (2)C3—C12—H12A109.5
C4A—C4—H4119.9C3—C12—H12B109.5
C3—C4—H4119.9H12A—C12—H12B109.5
C4—C4A—C9A122.05 (19)C3—C12—H12C109.5
C4—C4A—C4B131.18 (19)H12A—C12—H12C109.5
C9A—C4A—C4B106.74 (18)H12B—C12—H12C109.5
C5—C4B—C8A120.16 (18)C3—C12—H12D109.5
C5—C4B—C4A133.50 (19)H12A—C12—H12D141.1
C8A—C4B—C4A106.30 (18)H12B—C12—H12D56.3
C6—C5—C4B117.50 (19)H12C—C12—H12D56.3
C6—C5—H5121.3C3—C12—H12E109.5
C4B—C5—H5121.3H12A—C12—H12E56.3
C5—C6—C7123.19 (19)H12B—C12—H12E141.1
C5—C6—N6118.38 (19)H12C—C12—H12E56.3
C7—C6—N6118.42 (19)H12D—C12—H12E109.5
C8—C7—C6119.64 (19)C3—C12—H12F109.5
C8—C7—H7120.2H12A—C12—H12F56.3
C6—C7—H7120.2H12B—C12—H12F56.3
C7—C8—C8A118.28 (19)H12C—C12—H12F141.1
C7—C8—H8120.9H12D—C12—H12F109.5
C8A—C8—H8120.9H12E—C12—H12F109.5
O1B—N1—C1—C234.9 (3)C6—C7—C8—C8A0.1 (3)
O1A—N1—C1—C2141.1 (2)C9A—N9—C8A—C8179.9 (2)
O1B—N1—C1—C9A151.7 (2)C10—N9—C8A—C810.1 (3)
O1A—N1—C1—C9A32.3 (3)C9A—N9—C8A—C4B1.1 (2)
C9A—C1—C2—C31.7 (3)C10—N9—C8A—C4B168.90 (18)
N1—C1—C2—C3172.0 (2)C7—C8—C8A—N9177.8 (2)
C1—C2—C3—C40.3 (3)C7—C8—C8A—C4B1.1 (3)
C1—C2—C3—C12177.5 (2)C5—C4B—C8A—N9177.66 (18)
C2—C3—C4—C4A0.6 (3)C4A—C4B—C8A—N90.2 (2)
C12—C3—C4—C4A178.4 (2)C5—C4B—C8A—C81.4 (3)
C3—C4—C4A—C9A0.2 (3)C4A—C4B—C8A—C8179.30 (19)
C3—C4—C4A—C4B177.8 (2)C8A—N9—C9A—C1179.2 (2)
C4—C4A—C4B—C50.1 (4)C10—N9—C9A—C110.3 (4)
C9A—C4A—C4B—C5178.2 (2)C8A—N9—C9A—C4A1.5 (2)
C4—C4A—C4B—C8A177.6 (2)C10—N9—C9A—C4A167.38 (19)
C9A—C4A—C4B—C8A0.7 (2)C2—C1—C9A—N9175.6 (2)
C8A—C4B—C5—C60.4 (3)N1—C1—C9A—N911.2 (4)
C4A—C4B—C5—C6177.6 (2)C2—C1—C9A—C4A2.0 (3)
C4B—C5—C6—C70.8 (3)N1—C1—C9A—C4A171.21 (18)
C4B—C5—C6—N6178.08 (19)C4—C4A—C9A—N9177.09 (19)
O6A—N6—C6—C5175.9 (2)C4B—C4A—C9A—N91.4 (2)
O6B—N6—C6—C54.7 (3)C4—C4A—C9A—C11.1 (3)
O6A—N6—C6—C75.2 (3)C4B—C4A—C9A—C1179.53 (18)
O6B—N6—C6—C7174.2 (2)C8A—N9—C10—C1183.1 (3)
C5—C6—C7—C81.1 (3)C9A—N9—C10—C11109.3 (3)
N6—C6—C7—C8177.8 (2)
 

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