3-Chloro-1-ethyl-6-nitro-1H-indazole

In the title compound, C₉H₈ClN₃O₂, the terminal C atom of the ethyl group deviates from the indazole ring (r.m.s. deviation = 0.008 Å) by 1.588 (3) Å. The dihedral angle between the ring system and the attached nitro group is 2.8 (3)°. In the crystal, weak C—H...O inter­actions link the mol­ecules into zigzag chains propagating along [001]. In addition, weak π–π stacking inter­actions [centroid–centroid separations = 3.6809 (10) and 3.7393 (11) Å] help to consolidate the packing.

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 = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.168 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2 Report

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         45 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   2 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

3-Chloro-1-ethyl-6-nitro-1H-indazole

Crystal data

C9H8ClN3O2	F(000) = 464
Mr = 225.63	Dx = 1.485 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 7.4984 (3) Å	Cell parameters from 1252 reflections
b = 16.2805 (7) Å	θ = 6.0–70.9°
c = 8.3363 (3) Å	µ = 3.24 mm^−1
β = 97.403 (4)°	T = 293 K
V = 1009.19 (7) Å^3	Plate, yellow
Z = 4	0.22 × 0.20 × 0.06 mm

Data collection

Rigaku Oxford diffraction diffractometer	1916 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1572 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 16.0416 pixels mm^-1	θmax = 71.4°, θmin = 5.4°
ω scans	h = −7→9
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −19→16
Tmin = 0.493, Tmax = 1.000	l = −9→10
3567 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0591P)^2 + 0.080P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1916 reflections	Δρmax = 0.20 e Å^−3
137 parameters	Δρmin = −0.23 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All the H atoms were placed in calculated positions and refined using the riding model with C—H bond lengths of 0.93 Å (CH), 0.97 Å (CH₂) or 0.96 Å (CH₃). Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH₂) or 1.5 (CH₃) times U_eq of the parent atom. The methyl group was allowed to rotate, but not to tip, to best fit the electron density.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.34194 (8)	0.57002 (5)	0.22541 (6)	0.0741 (2)
O1	0.0801 (2)	0.38775 (13)	1.0161 (2)	0.0801 (5)
O2	0.0722 (3)	0.28363 (12)	0.8569 (3)	0.1041 (8)
N1	0.3183 (2)	0.63770 (11)	0.5077 (2)	0.0555 (4)
N2	0.2742 (2)	0.61772 (10)	0.6560 (2)	0.0506 (4)
N3	0.0963 (2)	0.35657 (12)	0.8854 (3)	0.0628 (5)
C1	0.2999 (2)	0.57001 (14)	0.4224 (2)	0.0516 (4)
C2	0.2448 (2)	0.50247 (12)	0.5101 (2)	0.0453 (4)
C3	0.2059 (2)	0.41950 (13)	0.4800 (3)	0.0528 (5)
H3	0.2124	0.3969	0.3785	0.063*
C4	0.1581 (3)	0.37243 (12)	0.6036 (3)	0.0556 (5)
H4	0.1329	0.3169	0.5876	0.067*
C5	0.1473 (2)	0.40879 (12)	0.7548 (2)	0.0487 (4)
C6	0.1812 (2)	0.48984 (12)	0.7903 (2)	0.0459 (4)
H6	0.1710	0.5121	0.8914	0.055*
C7	0.2320 (2)	0.53656 (11)	0.6633 (2)	0.0432 (4)
C8	0.3023 (3)	0.67764 (13)	0.7875 (3)	0.0585 (5)
H8A	0.2237	0.6646	0.8677	0.070*
H8B	0.2704	0.7319	0.7451	0.070*
C9	0.4930 (3)	0.67852 (18)	0.8667 (4)	0.0791 (7)
H9A	0.5700	0.6969	0.7905	0.119*
H9B	0.5276	0.6241	0.9027	0.119*
H9C	0.5038	0.7151	0.9577	0.119*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0669 (4)	0.1084 (5)	0.0482 (3)	0.0074 (3)	0.0124 (2)	0.0114 (3)
O1	0.0843 (12)	0.0871 (13)	0.0730 (11)	0.0025 (10)	0.0251 (9)	0.0224 (10)
O2	0.1397 (19)	0.0585 (11)	0.1091 (17)	−0.0275 (12)	−0.0026 (14)	0.0253 (11)
N1	0.0531 (9)	0.0547 (9)	0.0587 (9)	−0.0002 (7)	0.0078 (7)	0.0092 (8)
N2	0.0570 (9)	0.0410 (8)	0.0542 (9)	−0.0021 (7)	0.0091 (7)	−0.0008 (7)
N3	0.0548 (10)	0.0561 (10)	0.0754 (13)	−0.0035 (8)	0.0001 (8)	0.0195 (9)
C1	0.0413 (9)	0.0646 (12)	0.0490 (10)	0.0044 (8)	0.0054 (7)	0.0071 (9)
C2	0.0378 (8)	0.0516 (10)	0.0458 (9)	0.0060 (7)	0.0027 (7)	−0.0006 (8)
C3	0.0488 (10)	0.0549 (11)	0.0536 (11)	0.0079 (8)	0.0028 (8)	−0.0130 (9)
C4	0.0517 (10)	0.0405 (9)	0.0724 (13)	0.0040 (8)	−0.0001 (9)	−0.0066 (9)
C5	0.0408 (9)	0.0456 (9)	0.0583 (11)	0.0028 (7)	0.0015 (7)	0.0064 (8)
C6	0.0441 (9)	0.0474 (9)	0.0460 (9)	0.0023 (7)	0.0053 (7)	−0.0003 (7)
C7	0.0384 (8)	0.0418 (9)	0.0487 (9)	0.0020 (7)	0.0030 (6)	−0.0022 (7)
C8	0.0593 (12)	0.0447 (10)	0.0732 (13)	0.0006 (9)	0.0148 (9)	−0.0122 (9)
C9	0.0680 (14)	0.0823 (17)	0.0850 (17)	−0.0009 (13)	0.0020 (12)	−0.0333 (14)

Geometric parameters (Å, º)

Cl1—C1	1.712 (2)	C3—C4	1.369 (3)
O1—N3	1.222 (3)	C4—H4	0.9300
O2—N3	1.220 (3)	C4—C5	1.404 (3)
N1—N2	1.360 (2)	C5—C6	1.369 (3)
N1—C1	1.309 (3)	C6—H6	0.9300
N2—C7	1.362 (2)	C6—C7	1.396 (3)
N2—C8	1.462 (3)	C8—H8A	0.9700
N3—C5	1.470 (3)	C8—H8B	0.9700
C1—C2	1.411 (3)	C8—C9	1.496 (3)
C2—C3	1.398 (3)	C9—H9A	0.9600
C2—C7	1.407 (2)	C9—H9B	0.9600
C3—H3	0.9300	C9—H9C	0.9600
C1—N1—N2	105.75 (17)	C6—C5—N3	117.14 (18)
N1—N2—C7	110.95 (16)	C6—C5—C4	124.74 (19)
N1—N2—C8	119.57 (17)	C5—C6—H6	122.5
C7—N2—C8	128.75 (17)	C5—C6—C7	115.00 (17)
O1—N3—C5	119.02 (19)	C7—C6—H6	122.5
O2—N3—O1	123.3 (2)	N2—C7—C2	107.41 (16)
O2—N3—C5	117.7 (2)	N2—C7—C6	130.55 (17)
N1—C1—Cl1	120.10 (17)	C6—C7—C2	122.03 (17)
N1—C1—C2	113.08 (18)	N2—C8—H8A	109.2
C2—C1—Cl1	126.83 (17)	N2—C8—H8B	109.2
C3—C2—C1	136.70 (19)	N2—C8—C9	112.00 (18)
C3—C2—C7	120.51 (18)	H8A—C8—H8B	107.9
C7—C2—C1	102.79 (17)	C9—C8—H8A	109.2
C2—C3—H3	120.8	C9—C8—H8B	109.2
C4—C3—C2	118.32 (18)	C8—C9—H9A	109.5
C4—C3—H3	120.8	C8—C9—H9B	109.5
C3—C4—H4	120.3	C8—C9—H9C	109.5
C3—C4—C5	119.39 (18)	H9A—C9—H9B	109.5
C5—C4—H4	120.3	H9A—C9—H9C	109.5
C4—C5—N3	118.12 (19)	H9B—C9—H9C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2^i	0.93	2.52	3.280 (3)	139

Symmetry code: (i) x, −y+1/2, z−1/2.