Crystal structure and Hirshfeld surface analysis of 5-[(5-nitro-1H-indazol-1-yl)meth­yl]-3-phenyl-4,5-di­hydro­isoxazole

In the title compound the indazole portion is planar and the nitro group and the pendant phenyl ring are coplanar within 7°. Oblique stacks along the a-axis direction are formed by π–π-stacking inter­actions between the indazole unit and the pendant phenyl rings of adjacent mol­ecules. The stacks are linked into pairs through C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.120
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.41 Report
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.057 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             108.9 Degree
PLAT793_ALERT_4_G Model has Chirality at C9          (Centro SPGR)          R Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          8 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         17 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   2 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: 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).

5-[(5-Nitro-1H-indazol-1-yl)methyl]-3-phenyl-4,5-dihydroisoxazole

Crystal data

C17H14N4O3	F(000) = 672
Mr = 322.32	Dx = 1.504 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.8595 (4) Å	Cell parameters from 9953 reflections
b = 11.8831 (7) Å	θ = 2.7–29.1°
c = 15.5716 (9) Å	µ = 0.11 mm^−1
β = 101.853 (1)°	T = 100 K
V = 1423.30 (14) Å^3	Block, colourless
Z = 4	0.35 × 0.32 × 0.17 mm

Data collection

Bruker SMART APEX CCD diffractometer	3807 independent reflections
Radiation source: fine-focus sealed tube	3116 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 8.3333 pixels mm^-1	θmax = 29.1°, θmin = 2.2°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −16→16
Tmin = 0.90, Tmax = 0.98	l = −21→21
26832 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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F^2) = 0.120	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0692P)^2 + 0.3982P] where P = (Fo^2 + 2Fc^2)/3
3807 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.20 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.

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

	x	y	z	Uiso*/Ueq
O1	0.65493 (11)	0.74043 (7)	0.41423 (5)	0.0191 (2)
O2	0.30551 (13)	0.88196 (8)	−0.02290 (6)	0.0285 (2)
O3	0.20589 (12)	0.71575 (8)	−0.06215 (6)	0.0245 (2)
N1	0.69220 (13)	0.46778 (8)	0.25680 (7)	0.0185 (2)
N2	0.72589 (12)	0.57977 (8)	0.27365 (6)	0.0158 (2)
N3	0.74782 (13)	0.82212 (8)	0.47244 (7)	0.0174 (2)
N4	0.30425 (13)	0.77874 (9)	−0.01243 (7)	0.0189 (2)
C1	0.63510 (14)	0.64559 (10)	0.20885 (7)	0.0144 (2)
C2	0.62565 (15)	0.76290 (10)	0.19937 (8)	0.0169 (2)
H2	0.685 (2)	0.8130 (14)	0.2417 (11)	0.031 (4)*
C3	0.51782 (15)	0.80431 (10)	0.12540 (8)	0.0168 (2)
H3	0.504 (2)	0.8820 (14)	0.1145 (10)	0.024 (4)*
C4	0.42155 (14)	0.73017 (10)	0.06319 (7)	0.0161 (2)
C5	0.42849 (14)	0.61464 (10)	0.07119 (8)	0.0158 (2)
H5	0.357 (2)	0.5659 (14)	0.0287 (10)	0.028 (4)*
C6	0.53865 (14)	0.57188 (9)	0.14574 (8)	0.0152 (2)
C7	0.58181 (15)	0.46238 (10)	0.18078 (8)	0.0182 (2)
H7	0.542 (2)	0.3910 (13)	0.1558 (10)	0.025 (4)*
C8	0.84131 (15)	0.61131 (10)	0.35495 (7)	0.0171 (2)
H8A	0.9079 (18)	0.6778 (12)	0.3442 (9)	0.016 (3)*
H8B	0.9229 (18)	0.5481 (12)	0.3686 (9)	0.016 (3)*
C9	0.74607 (15)	0.63288 (10)	0.42928 (8)	0.0168 (2)
H9	0.6526 (19)	0.5757 (13)	0.4289 (10)	0.020 (4)*
C10	0.87110 (16)	0.64689 (10)	0.51745 (8)	0.0174 (2)
H10A	0.992 (2)	0.6201 (13)	0.5155 (10)	0.023 (4)*
H10B	0.829 (2)	0.6065 (13)	0.5660 (11)	0.023 (4)*
C11	0.86519 (14)	0.77242 (10)	0.52933 (7)	0.0153 (2)
C12	0.97578 (14)	0.83461 (10)	0.60166 (7)	0.0155 (2)
C13	0.96755 (15)	0.95199 (10)	0.60656 (8)	0.0184 (2)
H13	0.890 (2)	0.9941 (14)	0.5607 (11)	0.028 (4)*
C14	1.06651 (16)	1.00864 (11)	0.67741 (8)	0.0213 (3)
H14	1.060 (2)	1.0871 (16)	0.6806 (11)	0.035 (5)*
C15	1.17610 (16)	0.94898 (11)	0.74367 (8)	0.0214 (3)
H15	1.249 (2)	0.9886 (15)	0.7961 (11)	0.034 (4)*
C16	1.18699 (16)	0.83273 (11)	0.73863 (8)	0.0199 (2)
H16	1.256 (2)	0.7904 (14)	0.7837 (10)	0.026 (4)*
C17	1.08704 (15)	0.77535 (10)	0.66777 (8)	0.0177 (2)
H17	1.0992 (19)	0.6917 (13)	0.6650 (10)	0.024 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0189 (4)	0.0187 (4)	0.0176 (4)	0.0040 (3)	−0.0014 (3)	−0.0028 (3)
O2	0.0362 (6)	0.0189 (5)	0.0263 (5)	0.0060 (4)	−0.0030 (4)	0.0037 (4)
O3	0.0237 (5)	0.0280 (5)	0.0183 (4)	−0.0012 (4)	−0.0041 (4)	−0.0007 (4)
N1	0.0223 (5)	0.0131 (5)	0.0202 (5)	−0.0003 (4)	0.0045 (4)	−0.0004 (4)
N2	0.0183 (5)	0.0132 (5)	0.0147 (5)	0.0014 (3)	0.0008 (4)	−0.0005 (3)
N3	0.0181 (5)	0.0178 (5)	0.0157 (5)	0.0010 (4)	0.0021 (4)	−0.0012 (4)
N4	0.0194 (5)	0.0205 (5)	0.0159 (5)	0.0032 (4)	0.0016 (4)	0.0003 (4)
C1	0.0145 (5)	0.0151 (5)	0.0135 (5)	0.0005 (4)	0.0026 (4)	−0.0004 (4)
C2	0.0187 (5)	0.0146 (5)	0.0165 (5)	−0.0003 (4)	0.0017 (4)	−0.0022 (4)
C3	0.0181 (5)	0.0141 (5)	0.0181 (6)	0.0015 (4)	0.0035 (4)	0.0002 (4)
C4	0.0146 (5)	0.0196 (5)	0.0135 (5)	0.0024 (4)	0.0018 (4)	0.0010 (4)
C5	0.0144 (5)	0.0178 (5)	0.0150 (5)	−0.0008 (4)	0.0024 (4)	−0.0023 (4)
C6	0.0147 (5)	0.0150 (5)	0.0162 (5)	−0.0010 (4)	0.0044 (4)	−0.0019 (4)
C7	0.0195 (6)	0.0148 (5)	0.0203 (6)	−0.0016 (4)	0.0038 (4)	−0.0013 (4)
C8	0.0162 (5)	0.0184 (5)	0.0148 (5)	0.0019 (4)	−0.0010 (4)	−0.0008 (4)
C9	0.0180 (5)	0.0147 (5)	0.0169 (5)	0.0015 (4)	0.0016 (4)	0.0011 (4)
C10	0.0216 (6)	0.0150 (5)	0.0148 (5)	0.0027 (4)	0.0018 (4)	0.0004 (4)
C11	0.0165 (5)	0.0151 (5)	0.0147 (5)	0.0011 (4)	0.0039 (4)	0.0011 (4)
C12	0.0148 (5)	0.0175 (5)	0.0145 (5)	0.0008 (4)	0.0037 (4)	0.0013 (4)
C13	0.0174 (5)	0.0171 (5)	0.0201 (6)	0.0007 (4)	0.0022 (4)	0.0021 (4)
C14	0.0214 (6)	0.0175 (6)	0.0245 (6)	−0.0020 (4)	0.0034 (5)	−0.0012 (5)
C15	0.0202 (6)	0.0259 (6)	0.0179 (6)	−0.0036 (5)	0.0033 (5)	−0.0020 (5)
C16	0.0188 (6)	0.0256 (6)	0.0146 (5)	0.0005 (5)	0.0016 (4)	0.0033 (4)
C17	0.0193 (6)	0.0178 (5)	0.0160 (6)	0.0023 (4)	0.0039 (4)	0.0025 (4)

Geometric parameters (Å, º)

O1—N3	1.4230 (13)	C8—C9	1.5238 (16)
O1—C9	1.4603 (14)	C8—H8A	0.981 (15)
O2—N4	1.2377 (14)	C8—H8B	0.982 (15)
O3—N4	1.2294 (13)	C9—C10	1.5245 (17)
N1—C7	1.3176 (16)	C9—H9	1.000 (15)
N1—N2	1.3716 (13)	C10—C11	1.5050 (15)
N2—C1	1.3577 (14)	C10—H10A	1.006 (16)
N2—C8	1.4472 (15)	C10—H10B	1.007 (16)
N3—C11	1.2840 (15)	C11—C12	1.4724 (16)
N4—C4	1.4573 (15)	C12—C17	1.3966 (15)
C1—C2	1.4022 (16)	C12—C13	1.3991 (16)
C1—C6	1.4147 (15)	C13—C14	1.3866 (17)
C2—C3	1.3734 (16)	C13—H13	0.976 (16)
C2—H2	0.940 (17)	C14—C15	1.3943 (18)
C3—C4	1.4093 (16)	C14—H14	0.936 (19)
C3—H3	0.941 (16)	C15—C16	1.3873 (18)
C4—C5	1.3785 (16)	C15—H15	1.011 (18)
C5—C6	1.3936 (16)	C16—C17	1.3941 (17)
C5—H5	0.967 (17)	C16—H16	0.941 (16)
C6—C7	1.4248 (16)	C17—H17	1.000 (16)
C7—H7	0.959 (16)
N3—O1—C9	108.92 (8)	H8A—C8—H8B	107.8 (11)
C7—N1—N2	106.54 (9)	O1—C9—C8	109.07 (9)
C1—N2—N1	111.44 (9)	O1—C9—C10	104.66 (9)
C1—N2—C8	129.81 (10)	C8—C9—C10	112.09 (10)
N1—N2—C8	118.70 (9)	O1—C9—H9	105.0 (9)
C11—N3—O1	109.12 (9)	C8—C9—H9	110.8 (9)
O3—N4—O2	122.78 (10)	C10—C9—H9	114.6 (9)
O3—N4—C4	118.64 (10)	C11—C10—C9	100.86 (9)
O2—N4—C4	118.56 (10)	C11—C10—H10A	111.8 (9)
N2—C1—C2	131.25 (11)	C9—C10—H10A	112.0 (9)
N2—C1—C6	106.53 (10)	C11—C10—H10B	110.9 (9)
C2—C1—C6	122.22 (10)	C9—C10—H10B	111.9 (9)
C3—C2—C1	117.05 (11)	H10A—C10—H10B	109.2 (13)
C3—C2—H2	119.7 (10)	N3—C11—C12	121.64 (10)
C1—C2—H2	123.2 (10)	N3—C11—C10	114.02 (10)
C2—C3—C4	120.28 (11)	C12—C11—C10	124.27 (10)
C2—C3—H3	122.1 (10)	C17—C12—C13	119.43 (11)
C4—C3—H3	117.6 (10)	C17—C12—C11	119.51 (10)
C5—C4—C3	123.69 (11)	C13—C12—C11	121.03 (10)
C5—C4—N4	118.31 (10)	C14—C13—C12	120.18 (11)
C3—C4—N4	117.97 (10)	C14—C13—H13	119.8 (10)
C4—C5—C6	116.40 (10)	C12—C13—H13	120.0 (10)
C4—C5—H5	121.9 (10)	C13—C14—C15	120.15 (12)
C6—C5—H5	121.6 (10)	C13—C14—H14	119.8 (11)
C5—C6—C1	120.36 (10)	C15—C14—H14	120.0 (11)
C5—C6—C7	135.26 (11)	C16—C15—C14	120.02 (12)
C1—C6—C7	104.35 (10)	C16—C15—H15	118.5 (10)
N1—C7—C6	111.14 (10)	C14—C15—H15	121.4 (10)
N1—C7—H7	120.5 (9)	C15—C16—C17	120.03 (11)
C6—C7—H7	128.3 (9)	C15—C16—H16	121.5 (10)
N2—C8—C9	112.99 (10)	C17—C16—H16	118.4 (10)
N2—C8—H8A	108.6 (8)	C16—C17—C12	120.17 (11)
C9—C8—H8A	110.9 (8)	C16—C17—H17	118.5 (9)
N2—C8—H8B	104.8 (8)	C12—C17—H17	121.3 (9)
C9—C8—H8B	111.4 (8)
C7—N1—N2—C1	0.80 (13)	C1—C6—C7—N1	0.01 (13)
C7—N1—N2—C8	178.51 (10)	C1—N2—C8—C9	86.13 (14)
C9—O1—N3—C11	−10.56 (12)	N1—N2—C8—C9	−91.08 (12)
N1—N2—C1—C2	178.29 (11)	N3—O1—C9—C8	−104.57 (10)
C8—N2—C1—C2	0.9 (2)	N3—O1—C9—C10	15.55 (11)
N1—N2—C1—C6	−0.80 (12)	N2—C8—C9—O1	−73.99 (12)
C8—N2—C1—C6	−178.17 (11)	N2—C8—C9—C10	170.59 (9)
N2—C1—C2—C3	−179.03 (11)	O1—C9—C10—C11	−13.98 (11)
C6—C1—C2—C3	−0.06 (16)	C8—C9—C10—C11	104.09 (10)
C1—C2—C3—C4	0.43 (16)	O1—N3—C11—C12	−176.33 (9)
C2—C3—C4—C5	−0.33 (17)	O1—N3—C11—C10	0.66 (13)
C2—C3—C4—N4	177.74 (10)	C9—C10—C11—N3	8.74 (13)
O3—N4—C4—C5	5.90 (15)	C9—C10—C11—C12	−174.36 (10)
O2—N4—C4—C5	−175.49 (10)	N3—C11—C12—C17	172.37 (11)
O3—N4—C4—C3	−172.27 (10)	C10—C11—C12—C17	−4.30 (16)
O2—N4—C4—C3	6.33 (16)	N3—C11—C12—C13	−5.78 (17)
C3—C4—C5—C6	−0.17 (17)	C10—C11—C12—C13	177.55 (11)
N4—C4—C5—C6	−178.23 (10)	C17—C12—C13—C14	−1.29 (17)
C4—C5—C6—C1	0.53 (16)	C11—C12—C13—C14	176.86 (10)
C4—C5—C6—C7	178.17 (12)	C12—C13—C14—C15	0.67 (18)
N2—C1—C6—C5	178.75 (10)	C13—C14—C15—C16	0.31 (18)
C2—C1—C6—C5	−0.44 (17)	C14—C15—C16—C17	−0.66 (18)
N2—C1—C6—C7	0.47 (12)	C15—C16—C17—C12	0.03 (17)
C2—C1—C6—C7	−178.72 (10)	C13—C12—C17—C16	0.95 (17)
N2—N1—C7—C6	−0.48 (13)	C11—C12—C17—C16	−177.23 (10)
C5—C6—C7—N1	−177.89 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1^i	0.959 (16)	2.467 (16)	3.3877 (14)	160.9 (13)

Symmetry code: (i) −x+1, y−1/2, −z+1/2.