2,4,5-Tri­methoxy-1-nitro­benzene: a structure in the rare space group P4₂

The achiral title compound, C₉H₁₁NO₅, crystallizes as a chiral structure in space group P4₂. Short contacts between the nitro group and two methoxy groups on neighbouring mol­ecules can be seen, as can methoxy-methoxy contacts between the other methoxy groups not involved in this interaction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.118
• Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         N1

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           31.98
           From the CIF: _reflns_number_total               1895
           Count of symmetry unique reflns         1897
           Completeness (_total/calc)             99.89%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2,4,5-trimethoxy-1-nitrobenzene

Crystal data

C9H11NO5	Dx = 1.464 Mg m^−3
Mr = 213.19	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42	Cell parameters from 25 reflections
Hall symbol: P 4c	θ = 5.8–16.5°
a = 15.749 (9) Å	µ = 0.12 mm^−1
c = 3.900 (2) Å	T = 293 K
V = 967.3 (9) Å^3	Prism, yellow-green
Z = 4	0.3 × 0.3 × 0.2 mm
F(000) = 448

Data collection

Enraf–Nonius MACH3 diffractometer	Rint = 0.029
Radiation source: fine-focus sealed tube	θmax = 32.0°, θmin = 1.3°
Graphite monochromator	h = −23→19
ω/2θ scans	k = −23→19
5058 measured reflections	l = −5→0
1895 independent reflections	3 standard reflections every 60 min
1070 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	Only H-atom coordinates refined
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0635P)^2 + 0.0428P] where P = (Fo^2 + 2Fc^2)/3
1895 reflections	(Δ/σ)max = 0.041
169 parameters	Δρmax = 0.16 e Å^−3
1 restraint	Δρmin = −0.17 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
O4	0.37385 (9)	0.36342 (9)	0.0676 (6)	0.0536 (5)
O3	0.40971 (9)	0.20815 (9)	0.2237 (7)	0.0526 (5)
O1	0.11847 (10)	0.15313 (9)	0.5403 (6)	0.0567 (6)
C1	0.16345 (12)	0.28879 (12)	0.3483 (6)	0.0393 (5)
N1	0.07951 (11)	0.32485 (12)	0.3891 (8)	0.0520 (6)
C2	0.18201 (12)	0.20482 (13)	0.4324 (7)	0.0418 (5)
C5	0.30810 (12)	0.31550 (12)	0.1837 (7)	0.0399 (5)
C7	0.13922 (18)	0.06909 (15)	0.6428 (10)	0.0557 (7)
H7A	0.169 (2)	0.0376 (19)	0.456 (13)	0.084*
H7B	0.0879 (19)	0.0444 (19)	0.713 (13)	0.084*
H7C	0.177 (2)	0.069 (2)	0.838 (12)	0.084*
C3	0.26559 (13)	0.17736 (13)	0.3936 (8)	0.0430 (6)
H3	0.2795 (14)	0.1212 (14)	0.452 (9)	0.052*
C4	0.32791 (12)	0.23069 (13)	0.2712 (7)	0.0413 (6)
O5	0.02629 (12)	0.28761 (11)	0.5549 (10)	0.0944 (10)
O6	0.06519 (11)	0.39379 (13)	0.2601 (10)	0.0896 (10)
C9	0.35461 (16)	0.44731 (14)	−0.0422 (9)	0.0523 (7)
H9A	0.3096 (18)	0.4498 (19)	−0.229 (12)	0.078*
H9B	0.4082 (18)	0.4686 (18)	−0.119 (11)	0.078*
H9C	0.3319 (19)	0.482 (2)	0.151 (11)	0.078*
C8	0.43519 (17)	0.12489 (17)	0.3327 (11)	0.0587 (8)
H8A	0.423 (2)	0.117 (2)	0.582 (12)	0.088*
H8B	0.4971 (19)	0.1227 (19)	0.268 (11)	0.088*
H8C	0.403 (2)	0.080 (2)	0.186 (12)	0.088*
C6	0.22654 (13)	0.34291 (13)	0.2232 (8)	0.0413 (5)
H6	0.2113 (14)	0.3998 (14)	0.165 (9)	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0398 (7)	0.0434 (8)	0.0774 (16)	−0.0056 (6)	0.0022 (9)	0.0127 (9)
O3	0.0363 (7)	0.0435 (7)	0.0780 (14)	0.0020 (6)	−0.0004 (9)	0.0032 (9)
O1	0.0469 (8)	0.0439 (8)	0.0793 (16)	−0.0085 (6)	0.0066 (10)	0.0095 (10)
C1	0.0361 (9)	0.0402 (10)	0.0418 (14)	−0.0023 (8)	−0.0004 (10)	−0.0038 (10)
N1	0.0410 (9)	0.0425 (10)	0.0724 (16)	−0.0026 (7)	0.0035 (11)	−0.0082 (11)
C2	0.0432 (10)	0.0394 (10)	0.0428 (14)	−0.0081 (8)	−0.0003 (11)	−0.0029 (10)
C5	0.0383 (9)	0.0388 (9)	0.0427 (14)	−0.0054 (8)	−0.0025 (11)	0.0029 (10)
C7	0.0597 (14)	0.0448 (12)	0.063 (2)	−0.0068 (10)	0.0077 (14)	0.0112 (14)
C3	0.0451 (11)	0.0342 (9)	0.0497 (16)	−0.0010 (7)	−0.0031 (11)	0.0001 (11)
C4	0.0384 (10)	0.0378 (10)	0.0478 (16)	−0.0003 (7)	−0.0059 (10)	−0.0023 (10)
O5	0.0590 (10)	0.0588 (10)	0.165 (3)	−0.0013 (8)	0.0528 (16)	0.0037 (15)
O6	0.0546 (10)	0.0748 (12)	0.139 (3)	0.0196 (9)	0.0140 (15)	0.0343 (17)
C9	0.0538 (13)	0.0416 (11)	0.0615 (19)	−0.0060 (10)	0.0040 (14)	0.0071 (13)
C8	0.0479 (12)	0.0489 (13)	0.079 (2)	0.0081 (10)	−0.0057 (15)	0.0049 (15)
C6	0.0421 (10)	0.0353 (9)	0.0464 (15)	−0.0016 (8)	−0.0030 (11)	0.0015 (11)

Geometric parameters (Å, º)

O4—C5	1.359 (3)	C5—C4	1.413 (3)
O4—C9	1.421 (3)	C7—H7A	1.00 (4)
O3—C4	1.349 (2)	C7—H7B	0.94 (3)
O3—C8	1.436 (3)	C7—H7C	0.96 (4)
O1—C2	1.357 (3)	C3—C4	1.377 (3)
O1—C7	1.421 (3)	C3—H3	0.94 (2)
C1—C2	1.393 (3)	C9—H9A	1.02 (4)
C1—C6	1.397 (3)	C9—H9B	0.96 (3)
C1—N1	1.447 (3)	C9—H9C	1.00 (4)
N1—O5	1.210 (3)	C8—H8A	1.00 (5)
N1—O6	1.218 (3)	C8—H8B	1.01 (3)
C2—C3	1.394 (3)	C8—H8C	1.05 (4)
C5—C6	1.364 (3)	C6—H6	0.95 (2)
C5—O4—C9	117.01 (16)	C4—C3—C2	121.4 (2)
C4—O3—C8	117.81 (19)	C4—C3—H3	119.5 (14)
C2—O1—C7	118.46 (18)	C2—C3—H3	119.1 (14)
C2—C1—C6	120.80 (18)	O3—C4—C3	124.58 (19)
C2—C1—N1	122.55 (18)	O3—C4—C5	115.24 (18)
C6—C1—N1	116.64 (18)	C3—C4—C5	120.18 (18)
O5—N1—O6	121.6 (2)	O4—C9—H9A	113.6 (17)
O5—N1—C1	120.1 (2)	O4—C9—H9B	103.5 (18)
O6—N1—C1	118.3 (2)	H9A—C9—H9B	112 (3)
O1—C2—C3	122.96 (19)	O4—C9—H9C	111 (2)
O1—C2—C1	119.18 (17)	H9A—C9—H9C	106 (2)
C3—C2—C1	117.85 (18)	H9B—C9—H9C	111 (3)
O4—C5—C6	125.41 (18)	O3—C8—H8A	110 (2)
O4—C5—C4	115.92 (17)	O3—C8—H8B	103.1 (18)
C6—C5—C4	118.67 (19)	H8A—C8—H8B	116 (3)
O1—C7—H7A	111 (2)	O3—C8—H8C	108.6 (19)
O1—C7—H7B	105.7 (19)	H8A—C8—H8C	111 (3)
H7A—C7—H7B	114 (3)	H8B—C8—H8C	108 (3)
O1—C7—H7C	111.7 (19)	C5—C6—C1	121.07 (19)
H7A—C7—H7C	107 (3)	C5—C6—H6	120.4 (14)
H7B—C7—H7C	107 (4)	C1—C6—H6	118.5 (15)
C2—C1—N1—O5	13.3 (4)	C1—C2—C3—C4	−1.0 (4)
C6—C1—N1—O5	−165.9 (3)	C8—O3—C4—C3	−5.0 (4)
C2—C1—N1—O6	−168.5 (3)	C8—O3—C4—C5	175.3 (3)
C6—C1—N1—O6	12.4 (4)	C2—C3—C4—O3	−179.3 (3)
C7—O1—C2—C3	4.9 (5)	C2—C3—C4—C5	0.5 (4)
C7—O1—C2—C1	−176.6 (3)	O4—C5—C4—O3	−0.7 (4)
C6—C1—C2—O1	−177.4 (3)	C6—C5—C4—O3	179.7 (3)
N1—C1—C2—O1	3.5 (4)	O4—C5—C4—C3	179.5 (3)
C6—C1—C2—C3	1.2 (4)	C6—C5—C4—C3	0.0 (4)
N1—C1—C2—C3	−177.9 (3)	O4—C5—C6—C1	−179.3 (3)
C9—O4—C5—C6	−4.3 (4)	C4—C5—C6—C1	0.2 (4)
C9—O4—C5—C4	176.2 (3)	C2—C1—C6—C5	−0.8 (4)
O1—C2—C3—C4	177.5 (3)	N1—C1—C6—C5	178.4 (3)