1-Nitro-4-(1-propyn-1-yl)benzene

The title compound, C₉H₇NO₂, was prepared by alkynylation of 4-iodo­nitro­benzene with 1,3-dili­thio­propyne in the presence of 1 equivalent of CuI and catalytic amounts of Pd(PPh₃)₂Cl₂. The complete mol­ecule is generated by crystallographic twofold symmetry with the C—N and C—C[triple bond]C—C units lying on the rotation axis. No directional inter­actions beyond normal van der Waals contacts could be identified in the packing.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.057
• wR factor = 0.179
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter Within Range ......      2.500 Sigma
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.008 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.10 Report
PLAT300_ALERT_4_G Atom Site Occupancy of H9A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H9B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H9C        Constrained at        0.5 Check
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C4       - C7       .       1.45 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          7 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: shelXle (Hübschle, 2011); software used to prepare material for publication: publCIF (Westrip, 2010).

1-Nitro-4-(1-propyn-1-yl)benzene

Crystal data

C9H7NO2	F(000) = 336
Mr = 161.16	Dx = 1.391 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54178 Å
a = 7.3633 (13) Å	Cell parameters from 4037 reflections
b = 12.0641 (16) Å	θ = 6.3–68.4°
c = 8.9185 (19) Å	µ = 0.83 mm^−1
β = 103.738 (13)°	T = 100 K
V = 769.6 (2) Å^3	Block, pale yellow
Z = 4	0.15 × 0.13 × 0.10 mm

Data collection

Bruker D8 Venture diffractometer	571 reflections with I > 2σ(I)
Radiation source: Incoatec Microsource	Rint = 0.109
ω scans	θmax = 69.2°, θmin = 6.3°
Absorption correction: multi-scan (SADABS; Bruker, 2015)	h = −8→8
Tmin = 0.509, Tmax = 0.753	k = −14→14
7605 measured reflections	l = −10→10
717 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.179	w = 1/[σ^2(Fo^2) + (0.1002P)^2 + 0.5352P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
717 reflections	Δρmax = 0.26 e Å^−3
60 parameters	Δρmin = −0.37 e Å^−3
0 restraints	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0025 (10)

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 H atoms were located initially by difference Fourier synthesis and relocated to idealized locations (C—H = 0.95–0.98 Å) and refined as riding atoms.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.3309 (2)	0.64648 (13)	0.11827 (18)	0.0376 (6)
N1	0.250000	0.5986 (2)	0.000000	0.0286 (7)
C1	0.250000	0.4765 (2)	0.000000	0.0266 (8)
C2	0.3613 (3)	0.42172 (19)	0.1242 (2)	0.0286 (7)
H2	0.435644	0.461834	0.208422	0.034*
C3	0.3623 (3)	0.30639 (19)	0.1232 (3)	0.0299 (7)
H3	0.439548	0.266962	0.206608	0.036*
C4	0.250000	0.2484 (2)	0.000000	0.0282 (8)
C7	0.250000	0.1283 (2)	0.000000	0.0298 (8)
C8	0.250000	0.0292 (3)	0.000000	0.0317 (8)
C9	0.250000	−0.0924 (3)	0.000000	0.0337 (9)
H9A	0.132345	−0.119488	−0.065837	0.040*	0.5
H9B	0.262645	−0.119487	0.105581	0.040*	0.5
H9C	0.355010	−0.119487	−0.039745	0.040*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0414 (10)	0.0234 (10)	0.0409 (11)	−0.0031 (7)	−0.0042 (7)	−0.0041 (7)
N1	0.0262 (13)	0.0213 (14)	0.0351 (15)	0.000	0.0008 (10)	0.000
C1	0.0249 (15)	0.0172 (16)	0.0371 (18)	0.000	0.0058 (13)	0.000
C2	0.0262 (12)	0.0232 (13)	0.0333 (13)	−0.0029 (8)	0.0011 (9)	−0.0031 (9)
C3	0.0280 (12)	0.0238 (14)	0.0350 (14)	0.0020 (8)	0.0018 (9)	0.0051 (9)
C4	0.0273 (16)	0.0203 (17)	0.0373 (18)	0.000	0.0080 (12)	0.000
C7	0.0297 (17)	0.0205 (18)	0.0375 (19)	0.000	0.0048 (13)	0.000
C8	0.0285 (16)	0.026 (2)	0.0387 (19)	0.000	0.0041 (13)	0.000
C9	0.0313 (17)	0.0174 (17)	0.049 (2)	0.000	0.0021 (14)	0.000

Geometric parameters (Å, º)

N1—O1	1.226 (2)	C7—C8	1.195 (4)
N1—C1	1.473 (4)	C8—C9	1.468 (4)
C1—C2^i	1.380 (3)	C9—H9A	0.9800
C1—C2	1.380 (3)	C9—H9B	0.9800
C2—C3	1.391 (3)	C9—H9C	0.9800
C2—H2	0.9500	C9—H9A^i	0.9800
C3—C4	1.396 (3)	C9—H9B^i	0.9800
C3—H3	0.9500	C9—H9C^i	0.9800
C4—C7	1.449 (4)
O1—N1—O1^i	123.7 (3)	H9A—C9—H9B	109.5
O1—N1—C1	118.13 (13)	C8—C9—H9C	109.5
O1^i—N1—C1	118.13 (13)	H9A—C9—H9C	109.5
C2^i—C1—C2	122.8 (3)	H9B—C9—H9C	109.5
C2^i—C1—N1	118.59 (14)	C8—C9—H9A^i	109.474 (4)
C2—C1—N1	118.59 (14)	H9A—C9—H9A^i	141.1
C1—C2—C3	118.4 (2)	H9B—C9—H9A^i	56.3
C1—C2—H2	120.8	H9C—C9—H9A^i	56.2
C3—C2—H2	120.8	C8—C9—H9B^i	109.469 (5)
C2—C3—C4	120.2 (2)	H9A—C9—H9B^i	56.3
C2—C3—H3	119.9	H9B—C9—H9B^i	141.1
C4—C3—H3	119.9	H9C—C9—H9B^i	56.3
C3—C4—C3^i	119.9 (3)	H9A^i—C9—H9B^i	109.5
C3—C4—C7	120.06 (14)	C8—C9—H9C^i	109.469 (4)
C3^i—C4—C7	120.06 (14)	H9A—C9—H9C^i	56.2
C8—C7—C4	180.0	H9B—C9—H9C^i	56.3
C7—C8—C9	180.0	H9C—C9—H9C^i	141.1
C8—C9—H9A	109.5	H9A^i—C9—H9C^i	109.5
C8—C9—H9B	109.5	H9B^i—C9—H9C^i	109.5
O1—N1—C1—C2^i	171.25 (14)	N1—C1—C2—C3	−179.44 (14)
O1^i—N1—C1—C2^i	−8.75 (14)	C1—C2—C3—C4	−1.1 (3)
O1—N1—C1—C2	−8.75 (14)	C2—C3—C4—C3^i	0.57 (14)
O1^i—N1—C1—C2	171.25 (14)	C2—C3—C4—C7	−179.43 (14)
C2^i—C1—C2—C3	0.56 (14)

Symmetry code: (i) −x+1/2, y, −z.