1,1,3,3-Tetra­ethyl-5-nitro­isoindoline

Tapmeyer, L.; Beske, M.; Plackmeyer, J.

doi:10.1107/S2414314619016298

1,1,3,3-Tetraethyl-5-nitroisoindoline

The title compound, C₁₆H₂₄N₂O₂, previously obtained as a yellow oil, exhibits a rather low melting point close to room temperature 297–298 K). In the molecule, the isoindoline ring system is approximately planar and coplanar to the nitro group, forming a dihedral angle of 5.63 (15)°. In the crystal, only weak N—H

O and C—H

π interactions are observed, linking molecules into chains parallel to the [101] direction.

Keywords: crystal structure; structure–property relationship; organic synthesis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314619016298/rz4034sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314619016298/rz4034Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314619016298/rz4034Isup3.cml Supplementary material

CCDC reference: 1969794

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R factor = 0.051
wR factor = 0.134
Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF019_ALERT_1_A  _diffrn_standards_number is missing
            Number of standards used in measurement.

Author Response: Area detector used.

DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.

Author Response: Area detector used.

DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

Author Response: Area detector used.


Alert level B
CRYSS02_ALERT_3_B  The value of _exptl_crystal_size_max is > 1.0
   Maximum crystal size given =   1.200

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.967 Why?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O82      --N8       .        5.1 s.u.
PLAT420_ALERT_2_C D-H Without Acceptor       N2       --H2       .     Please Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2       ..O81      .       2.63 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.365 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         92 Report

Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       1.20 mm
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         19 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

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

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

Computing details top

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: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2006) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

1,1,3,3-Tetraethyl-5-nitroisoindoline top

Crystal data top

C₁₆H₂₄N₂O₂	D_x = 1.199 Mg m⁻³
M_r = 276.37	Melting point: 297 K
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 9.0277 (6) Å	Cell parameters from 130 reflections
b = 19.9356 (13) Å	θ = 2.4–67.7°
c = 9.4811 (7) Å	µ = 0.63 mm⁻¹
β = 116.169 (2)°	T = 173 K
V = 1531.43 (18) Å³	Elongated block, pale yellow
Z = 4	1.20 × 0.60 × 0.60 mm
F(000) = 600

Data collection top

Siemens Bruker three circle diffractometer	2699 reflections with I > 2σ(I)
Radiation source: Incoatec microfocus tube, X-Ray microfocus tube	R_int = 0.053
ω and Phi scans	θ_max = 69.7°, θ_min = 4.4°
Absorption correction: multi-scan (SADABS; Bruker, 2015)	h = −10→10
T_min = 0.568, T_max = 0.753	k = −24→24
32894 measured reflections	l = −10→11
2769 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.0661P)² + 0.6801P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.134	(Δ/σ)_max < 0.001
S = 1.09	Δρ_max = 0.38 e Å⁻³
2769 reflections	Δρ_min = −0.25 e Å⁻³
185 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.034 (2)

Special details top

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. The H atom on nitrogen N2 was located in a difference Fourier map and refined freely with U_iso(H) = 1.2 U_eq(N). All other H atoms were treated as riding, with C–H = 0.96–0.98 Å, and with with U_iso(H) = 1.2 U_eq(C) or 1.5 U_eq(C) for methyl H atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.52355 (17)	0.63396 (7)	0.61223 (17)	0.0270 (3)
N2	0.68275 (15)	0.65271 (7)	0.61351 (15)	0.0293 (3)
H2	0.763 (2)	0.6336 (10)	0.692 (2)	0.035*
C11	0.5343 (2)	0.57151 (8)	0.71234 (18)	0.0329 (4)
H11A	0.421439	0.559790	0.696521	0.039*
H11B	0.576055	0.533516	0.672895	0.039*
C12	0.6438 (2)	0.57893 (10)	0.8882 (2)	0.0420 (4)
H12A	0.642818	0.536966	0.941621	0.063*
H12B	0.756909	0.589122	0.906117	0.063*
H12C	0.601917	0.615460	0.929801	0.063*
C13	0.4529 (2)	0.69406 (8)	0.6662 (2)	0.0360 (4)
H13A	0.348788	0.679891	0.668267	0.043*
H13B	0.531851	0.706068	0.774917	0.043*
C14	0.4189 (3)	0.75591 (10)	0.5640 (3)	0.0530 (5)
H14A	0.374684	0.791465	0.605935	0.080*
H14B	0.521776	0.771261	0.563372	0.080*
H14C	0.338389	0.745038	0.456534	0.080*
C3	0.68746 (17)	0.63829 (7)	0.46225 (16)	0.0256 (3)
C31	0.79690 (18)	0.57636 (8)	0.47844 (18)	0.0311 (4)
H31A	0.907820	0.584989	0.564874	0.037*
H31B	0.749758	0.537598	0.510014	0.037*
C32	0.8174 (2)	0.55661 (9)	0.3331 (2)	0.0385 (4)
H32A	0.888629	0.517002	0.356522	0.058*
H32B	0.709085	0.546275	0.247067	0.058*
H32C	0.867657	0.593819	0.302103	0.058*
C33	0.74827 (19)	0.70079 (8)	0.40784 (19)	0.0326 (4)
H33A	0.739947	0.692250	0.301727	0.039*
H33B	0.674711	0.738960	0.399550	0.039*
C34	0.9256 (2)	0.72039 (10)	0.5175 (2)	0.0448 (5)
H34A	0.956411	0.760343	0.476221	0.067*
H34B	0.934523	0.730088	0.622251	0.067*
H34C	0.999824	0.683331	0.524330	0.067*
C3A	0.50770 (17)	0.62372 (7)	0.35502 (17)	0.0251 (3)
C4	0.43042 (18)	0.61567 (7)	0.19321 (17)	0.0277 (3)
H4	0.489482	0.620820	0.132134	0.033*
C5	0.26335 (18)	0.59978 (8)	0.12360 (17)	0.0300 (4)
C6	0.17277 (18)	0.59141 (8)	0.20808 (19)	0.0334 (4)
H6	0.059749	0.578847	0.156877	0.040*
C7A	0.41760 (17)	0.61856 (7)	0.44111 (17)	0.0263 (3)
C7	0.25063 (18)	0.60177 (8)	0.36886 (19)	0.0322 (4)
H7	0.190803	0.597473	0.429440	0.039*
N8	0.17901 (16)	0.59159 (8)	−0.04799 (16)	0.0380 (4)
O81	0.03459 (17)	0.57346 (10)	−0.10830 (17)	0.0695 (5)
O82	0.25620 (17)	0.60204 (9)	−0.12333 (14)	0.0549 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0263 (7)	0.0337 (8)	0.0227 (7)	−0.0013 (5)	0.0123 (6)	−0.0024 (6)
N2	0.0250 (6)	0.0415 (7)	0.0214 (6)	−0.0035 (5)	0.0102 (5)	−0.0032 (5)
C11	0.0368 (8)	0.0377 (8)	0.0269 (8)	−0.0023 (6)	0.0167 (7)	0.0001 (6)
C12	0.0455 (10)	0.0532 (10)	0.0280 (9)	0.0019 (8)	0.0168 (8)	0.0047 (7)
C13	0.0369 (8)	0.0407 (9)	0.0345 (9)	0.0017 (7)	0.0195 (7)	−0.0072 (7)
C14	0.0658 (13)	0.0385 (9)	0.0583 (12)	0.0112 (9)	0.0306 (11)	−0.0021 (8)
C3	0.0233 (7)	0.0316 (7)	0.0215 (7)	−0.0014 (5)	0.0095 (6)	−0.0014 (5)
C31	0.0264 (7)	0.0371 (8)	0.0264 (8)	0.0036 (6)	0.0085 (6)	0.0002 (6)
C32	0.0313 (8)	0.0490 (10)	0.0366 (9)	0.0061 (7)	0.0162 (7)	−0.0054 (7)
C33	0.0321 (8)	0.0369 (8)	0.0297 (8)	−0.0049 (6)	0.0144 (7)	0.0008 (6)
C34	0.0388 (9)	0.0504 (10)	0.0442 (10)	−0.0163 (8)	0.0173 (8)	−0.0043 (8)
C3A	0.0241 (7)	0.0269 (7)	0.0236 (7)	0.0010 (5)	0.0100 (6)	0.0007 (5)
C4	0.0257 (7)	0.0340 (7)	0.0240 (7)	0.0014 (5)	0.0114 (6)	0.0011 (6)
C5	0.0264 (7)	0.0365 (8)	0.0223 (8)	0.0037 (6)	0.0064 (6)	−0.0002 (6)
C6	0.0216 (7)	0.0442 (9)	0.0316 (8)	−0.0001 (6)	0.0091 (6)	−0.0018 (6)
C7A	0.0260 (7)	0.0281 (7)	0.0250 (8)	0.0012 (5)	0.0114 (6)	−0.0004 (5)
C7	0.0256 (7)	0.0427 (9)	0.0310 (8)	−0.0001 (6)	0.0149 (6)	−0.0009 (6)
N8	0.0282 (7)	0.0529 (9)	0.0256 (7)	0.0028 (6)	0.0053 (6)	−0.0014 (6)
O81	0.0307 (7)	0.1309 (15)	0.0340 (7)	−0.0130 (8)	0.0026 (6)	−0.0086 (8)
O82	0.0455 (8)	0.0941 (11)	0.0257 (6)	−0.0105 (7)	0.0161 (6)	−0.0053 (6)

Geometric parameters (Å, º) top

C1—N2	1.4799 (18)	C31—H31B	0.9900
C1—C7A	1.5075 (19)	C32—H32A	0.9800
C1—C11	1.542 (2)	C32—H32B	0.9800
C1—C13	1.547 (2)	C32—H32C	0.9800
N2—C3	1.4815 (19)	C33—C34	1.526 (2)
N2—H2	0.86 (2)	C33—H33A	0.9900
C11—C12	1.525 (2)	C33—H33B	0.9900
C11—H11A	0.9900	C34—H34A	0.9800
C11—H11B	0.9900	C34—H34B	0.9800
C12—H12A	0.9800	C34—H34C	0.9800
C12—H12B	0.9800	C3A—C4	1.386 (2)
C12—H12C	0.9800	C3A—C7A	1.387 (2)
C13—C14	1.513 (3)	C4—C5	1.390 (2)
C13—H13A	0.9900	C4—H4	0.9500
C13—H13B	0.9900	C5—C6	1.384 (2)
C14—H14A	0.9800	C5—N8	1.470 (2)
C14—H14B	0.9800	C6—C7	1.384 (2)
C14—H14C	0.9800	C6—H6	0.9500
C3—C3A	1.5153 (19)	C7A—C7	1.394 (2)
C3—C33	1.540 (2)	C7—H7	0.9500
C3—C31	1.546 (2)	N8—O82	1.216 (2)
C31—C32	1.521 (2)	N8—O81	1.225 (2)
C31—H31A	0.9900

N2—C1—C7A	102.31 (11)	C32—C31—H31B	108.2
N2—C1—C11	113.68 (12)	C3—C31—H31B	108.2
C7A—C1—C11	109.62 (12)	H31A—C31—H31B	107.3
N2—C1—C13	110.01 (12)	C31—C32—H32A	109.5
C7A—C1—C13	110.81 (12)	C31—C32—H32B	109.5
C11—C1—C13	110.18 (12)	H32A—C32—H32B	109.5
C1—N2—C3	112.66 (11)	C31—C32—H32C	109.5
C1—N2—H2	110.0 (13)	H32A—C32—H32C	109.5
C3—N2—H2	111.8 (13)	H32B—C32—H32C	109.5
C12—C11—C1	115.41 (13)	C34—C33—C3	113.65 (13)
C12—C11—H11A	108.4	C34—C33—H33A	108.8
C1—C11—H11A	108.4	C3—C33—H33A	108.8
C12—C11—H11B	108.4	C34—C33—H33B	108.8
C1—C11—H11B	108.4	C3—C33—H33B	108.8
H11A—C11—H11B	107.5	H33A—C33—H33B	107.7
C11—C12—H12A	109.5	C33—C34—H34A	109.5
C11—C12—H12B	109.5	C33—C34—H34B	109.5
H12A—C12—H12B	109.5	H34A—C34—H34B	109.5
C11—C12—H12C	109.5	C33—C34—H34C	109.5
H12A—C12—H12C	109.5	H34A—C34—H34C	109.5
H12B—C12—H12C	109.5	H34B—C34—H34C	109.5
C14—C13—C1	114.59 (14)	C4—C3A—C7A	120.20 (13)
C14—C13—H13A	108.6	C4—C3A—C3	129.19 (13)
C1—C13—H13A	108.6	C7A—C3A—C3	110.60 (12)
C14—C13—H13B	108.6	C3A—C4—C5	117.57 (14)
C1—C13—H13B	108.6	C3A—C4—H4	121.2
H13A—C13—H13B	107.6	C5—C4—H4	121.2
C13—C14—H14A	109.5	C6—C5—C4	123.15 (14)
C13—C14—H14B	109.5	C6—C5—N8	118.51 (13)
H14A—C14—H14B	109.5	C4—C5—N8	118.34 (14)
C13—C14—H14C	109.5	C7—C6—C5	118.47 (14)
H14A—C14—H14C	109.5	C7—C6—H6	120.8
H14B—C14—H14C	109.5	C5—C6—H6	120.8
N2—C3—C3A	101.96 (11)	C3A—C7A—C7	121.09 (14)
N2—C3—C33	109.51 (12)	C3A—C7A—C1	111.09 (12)
C3A—C3—C33	111.40 (12)	C7—C7A—C1	127.82 (14)
N2—C3—C31	110.41 (12)	C6—C7—C7A	119.41 (14)
C3A—C3—C31	111.23 (12)	C6—C7—H7	120.3
C33—C3—C31	111.90 (12)	C7A—C7—H7	120.3
C32—C31—C3	116.40 (13)	O82—N8—O81	122.97 (15)
C32—C31—H31A	108.2	O82—N8—C5	118.68 (13)
C3—C31—H31A	108.2	O81—N8—C5	118.34 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C3A/C4/C5/C6/C7/C7A benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O81ⁱ	0.865 (15)	2.634 (16)	3.4860 (18)	168.4 (16)
C11—H11B···Cg1ⁱⁱ	0.99	2.91	3.7552 (18)	144

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

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1,1,3,3-Tetra­ethyl-5-nitro­isoindoline

Supporting information

Key indicators

checkCIF/PLATON results

1,1,3,3-Tetraethyl-5-nitroisoindoline