1-Chloro-3-(6-nitro-1H-indazol-1-yl)propan-2-ol

In the title compound, C₁₀H₁₀ClN₃O₃, the side chain is oriented nearly perpendicular to the mean plane of the indazole ring system. In the crystal, complementary sets of O—H...N and C—H...O hydrogen bonds form chains of mol­ecules stacked along the a-axis direction

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.151
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.23 Report
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N3 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT793_ALERT_4_G The Model has Chirality at C9      (Centro SPGR)          S Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         19 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

1-Chloro-3-(6-nitro-1H-indazol-1-yl)propan-2-ol

Crystal data

C10H10ClN3O3	Z = 2
Mr = 255.66	F(000) = 264
Triclinic, P1	Dx = 1.513 Mg m^−3
a = 4.3949 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9144 (8) Å	Cell parameters from 3584 reflections
c = 13.1376 (11) Å	θ = 2.4–27.0°
α = 98.481 (1)°	µ = 0.34 mm^−1
β = 90.755 (1)°	T = 298 K
γ = 97.377 (1)°	Plate, pale yellow
V = 561.19 (8) Å^3	0.45 × 0.20 × 0.11 mm

Data collection

Bruker SMART APEX CCD diffractometer	2790 independent reflections
Radiation source: fine-focus sealed tube	1874 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.3333 pixels mm^-1	θmax = 28.4°, θmin = 1.6°
φ and ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −13→13
Tmin = 0.87, Tmax = 0.96	l = −17→17
10444 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0916P)^2] where P = (Fo^2 + 2Fc^2)/3
2790 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 20 sec/frame.

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. 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 > 2sigma(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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) while that attached to oxygen was placed in a location derived from a difference map and its coordinates adjusted to give O—H = 1.00 %A. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

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

	x	y	z	Uiso*/Ueq
Cl1	0.46205 (13)	0.09914 (5)	0.12647 (5)	0.0763 (2)
O1	0.8217 (5)	0.6041 (2)	0.57705 (12)	0.0975 (6)
O2	1.1879 (6)	0.7675 (3)	0.61324 (14)	0.1311 (9)
O3	0.7011 (3)	0.38489 (14)	0.07195 (10)	0.0562 (4)
H3	0.562	0.362	0.0091	0.084*
N1	0.5788 (3)	0.63286 (15)	0.19817 (10)	0.0462 (4)
N2	0.6434 (4)	0.70386 (16)	0.11859 (11)	0.0544 (4)
N3	0.9933 (5)	0.6999 (2)	0.55419 (13)	0.0732 (5)
C1	0.7535 (4)	0.69161 (17)	0.28323 (12)	0.0428 (4)
C2	0.7652 (4)	0.65277 (18)	0.38148 (13)	0.0480 (4)
H2	0.6441	0.5758	0.3985	0.058*
C3	0.9679 (5)	0.7365 (2)	0.45025 (13)	0.0530 (5)
C4	1.1529 (5)	0.8533 (2)	0.42777 (15)	0.0617 (5)
H4	1.2851	0.9064	0.4784	0.074*
C5	1.1401 (5)	0.8896 (2)	0.33168 (15)	0.0590 (5)
H5	1.2633	0.9666	0.3157	0.071*
C6	0.9353 (4)	0.80712 (18)	0.25730 (13)	0.0479 (4)
C7	0.8535 (5)	0.80725 (19)	0.15292 (14)	0.0573 (5)
H7	0.9381	0.8724	0.1136	0.069*
C8	0.3623 (4)	0.50762 (18)	0.18429 (13)	0.0472 (4)
H8A	0.2181	0.5100	0.1283	0.057*
H8B	0.2472	0.5025	0.2464	0.057*
C9	0.5248 (4)	0.37983 (17)	0.16051 (12)	0.0454 (4)
H9	0.6651	0.3783	0.2188	0.054*
C10	0.2891 (4)	0.25374 (19)	0.15235 (15)	0.0558 (5)
H10A	0.1403	0.2559	0.0976	0.067*
H10B	0.1810	0.2545	0.2163	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0755 (4)	0.0445 (3)	0.1061 (5)	0.0009 (2)	0.0158 (3)	0.0074 (3)
O1	0.1276 (16)	0.1079 (15)	0.0554 (9)	−0.0111 (12)	0.0029 (9)	0.0302 (9)
O2	0.155 (2)	0.160 (2)	0.0647 (11)	−0.0362 (17)	−0.0454 (12)	0.0256 (12)
O3	0.0470 (7)	0.0696 (9)	0.0496 (7)	−0.0046 (6)	0.0041 (6)	0.0116 (6)
N1	0.0480 (8)	0.0474 (8)	0.0427 (7)	0.0006 (6)	−0.0045 (6)	0.0104 (6)
N2	0.0634 (10)	0.0521 (9)	0.0482 (8)	−0.0007 (7)	−0.0047 (7)	0.0170 (7)
N3	0.0903 (14)	0.0835 (14)	0.0437 (9)	0.0053 (11)	−0.0071 (9)	0.0086 (9)
C1	0.0427 (9)	0.0418 (8)	0.0436 (9)	0.0066 (7)	0.0001 (7)	0.0048 (7)
C2	0.0517 (10)	0.0478 (9)	0.0445 (9)	0.0037 (8)	0.0037 (7)	0.0088 (7)
C3	0.0599 (11)	0.0582 (11)	0.0402 (9)	0.0097 (9)	−0.0023 (8)	0.0034 (8)
C4	0.0656 (13)	0.0588 (12)	0.0537 (11)	−0.0032 (9)	−0.0113 (9)	−0.0031 (9)
C5	0.0633 (12)	0.0480 (10)	0.0610 (11)	−0.0078 (9)	−0.0014 (9)	0.0060 (9)
C6	0.0517 (10)	0.0420 (9)	0.0497 (9)	0.0027 (7)	0.0008 (8)	0.0090 (7)
C7	0.0695 (13)	0.0491 (10)	0.0534 (10)	−0.0038 (9)	−0.0020 (9)	0.0176 (8)
C8	0.0400 (9)	0.0514 (10)	0.0482 (9)	−0.0030 (7)	−0.0009 (7)	0.0090 (7)
C9	0.0427 (9)	0.0503 (9)	0.0421 (8)	−0.0029 (7)	0.0003 (7)	0.0115 (7)
C10	0.0515 (11)	0.0519 (10)	0.0613 (11)	−0.0042 (8)	0.0070 (9)	0.0092 (8)

Geometric parameters (Å, º)

Cl1—C10	1.787 (2)	C3—C4	1.398 (3)
O1—N3	1.211 (3)	C4—C5	1.365 (3)
O2—N3	1.210 (3)	C4—H4	0.9300
O3—C9	1.4098 (19)	C5—C6	1.409 (3)
O3—H3	1.0000	C5—H5	0.9300
N1—N2	1.357 (2)	C6—C7	1.413 (2)
N1—C1	1.360 (2)	C7—H7	0.9300
N1—C8	1.451 (2)	C8—C9	1.528 (3)
N2—C7	1.310 (2)	C8—H8A	0.9700
N3—C3	1.470 (3)	C8—H8B	0.9700
C1—C6	1.398 (2)	C9—C10	1.507 (2)
C1—C2	1.403 (2)	C9—H9	0.9800
C2—C3	1.366 (3)	C10—H10A	0.9700
C2—H2	0.9300	C10—H10B	0.9700
C9—O3—H3	109.5	C1—C6—C7	104.02 (15)
N2—N1—C1	110.65 (14)	C5—C6—C7	136.27 (17)
N2—N1—C8	120.76 (13)	N2—C7—C6	111.41 (15)
C1—N1—C8	128.49 (14)	N2—C7—H7	124.3
C7—N2—N1	106.79 (14)	C6—C7—H7	124.3
O2—N3—O1	122.9 (2)	N1—C8—C9	111.61 (14)
O2—N3—C3	117.9 (2)	N1—C8—H8A	109.3
O1—N3—C3	119.21 (19)	C9—C8—H8A	109.3
N1—C1—C6	107.13 (14)	N1—C8—H8B	109.3
N1—C1—C2	130.19 (16)	C9—C8—H8B	109.3
C6—C1—C2	122.68 (16)	H8A—C8—H8B	108.0
C3—C2—C1	114.95 (17)	O3—C9—C10	113.23 (14)
C3—C2—H2	122.5	O3—C9—C8	111.05 (13)
C1—C2—H2	122.5	C10—C9—C8	108.81 (15)
C2—C3—C4	124.27 (17)	O3—C9—H9	107.9
C2—C3—N3	117.44 (18)	C10—C9—H9	107.9
C4—C3—N3	118.29 (17)	C8—C9—H9	107.9
C5—C4—C3	120.15 (17)	C9—C10—Cl1	111.62 (14)
C5—C4—H4	119.9	C9—C10—H10A	109.3
C3—C4—H4	119.9	Cl1—C10—H10A	109.3
C4—C5—C6	118.24 (18)	C9—C10—H10B	109.3
C4—C5—H5	120.9	Cl1—C10—H10B	109.3
C6—C5—H5	120.9	H10A—C10—H10B	108.0
C1—C6—C5	119.71 (16)
C1—N1—N2—C7	−0.7 (2)	C3—C4—C5—C6	0.5 (3)
C8—N1—N2—C7	−177.30 (17)	N1—C1—C6—C5	179.55 (16)
N2—N1—C1—C6	1.0 (2)	C2—C1—C6—C5	−0.1 (3)
C8—N1—C1—C6	177.20 (16)	N1—C1—C6—C7	−0.8 (2)
N2—N1—C1—C2	−179.43 (17)	C2—C1—C6—C7	179.58 (16)
C8—N1—C1—C2	−3.2 (3)	C4—C5—C6—C1	−0.2 (3)
N1—C1—C2—C3	−179.49 (18)	C4—C5—C6—C7	−179.7 (2)
C6—C1—C2—C3	0.0 (3)	N1—N2—C7—C6	0.2 (2)
C1—C2—C3—C4	0.3 (3)	C1—C6—C7—N2	0.4 (2)
C1—C2—C3—N3	−179.21 (16)	C5—C6—C7—N2	179.9 (2)
O2—N3—C3—C2	174.7 (2)	N2—N1—C8—C9	94.92 (18)
O1—N3—C3—C2	−5.0 (3)	C1—N1—C8—C9	−81.0 (2)
O2—N3—C3—C4	−4.8 (3)	N1—C8—C9—O3	−57.54 (17)
O1—N3—C3—C4	175.5 (2)	N1—C8—C9—C10	177.18 (13)
C2—C3—C4—C5	−0.6 (3)	O3—C9—C10—Cl1	56.88 (18)
N3—C3—C4—C5	178.9 (2)	C8—C9—C10—Cl1	−179.12 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2^i	1.00	1.88	2.871 (2)	169
C2—H2···O1^ii	0.93	2.59	3.492 (3)	163
C10—H10A···O3^iii	0.97	2.49	3.268 (3)	137

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z.