Synthesis, crystal structure and spectroscopic and Hirshfeld surface analysis of 4-hy­droxy-3-meth­oxy-5-nitro­benzaldehyde

The title mol­ecule is planar with an r.m.s. deviation for all non-hydrogen atoms of 0.018 Å. An intra­molecular O1—H1...O5 hydrogen bond involving the adjacent hydroxyl and nitro groups closes an S(6) ring motif.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.174
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C8 H7 N O5
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         19 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         10 Note

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.20 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         21 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 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
   8 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2017 (Sheldrick, 2015), PLATON (Spek, 2020) and publCIF (Westrip, 2010).

4-Hydroxy-3-methoxy-5-nitrobenzaldehyde

Crystal data

C8H7NO5	F(000) = 408
Mr = 197.15	Dx = 1.568 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 2167 reflections
a = 6.8249 (2) Å	θ = 3.2–75.6°
b = 14.3395 (5) Å	µ = 1.16 mm^−1
c = 8.9089 (3) Å	T = 293 K
β = 106.678 (4)°	Block, yellow
V = 835.21 (5) Å^3	0.30 × 0.15 × 0.13 mm
Z = 4

Data collection

Rigaku Xcalibur Ruby Nova diffractometer	1697 independent reflections
Radiation source: micro-focus sealed X-ray tube	1574 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.016
Detector resolution: 10.4323 pixels mm^-1	θmax = 76.0°, θmin = 6.8°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	k = −16→17
Tmin = 0.647, Tmax = 1	l = −7→11
3633 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.174	H-atom parameters constrained
S = 0.81	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
1697 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
O1	0.24420 (14)	0.44411 (6)	0.92251 (10)	0.0442 (3)
H1	0.258885	0.488242	0.868197	0.066*
O2	0.19059 (16)	0.31818 (6)	1.10856 (11)	0.0506 (3)
O3	0.23301 (16)	0.48763 (7)	1.62543 (10)	0.0508 (3)
O4	0.3265 (2)	0.72037 (7)	1.06656 (14)	0.0655 (4)
O5	0.29317 (17)	0.62262 (8)	0.87895 (11)	0.0547 (3)
N1	0.30056 (15)	0.64166 (7)	1.01585 (12)	0.0422 (3)
C1	0.27609 (15)	0.56669 (8)	1.11855 (13)	0.0353 (3)
C2	0.24838 (14)	0.47461 (7)	1.06403 (13)	0.0347 (3)
C3	0.22165 (16)	0.40479 (8)	1.17059 (14)	0.0375 (3)
C4	0.22427 (16)	0.42865 (8)	1.32044 (13)	0.0386 (3)
H4	0.206582	0.382706	1.389078	0.046*
C5	0.25347 (16)	0.52194 (8)	1.37123 (13)	0.0377 (3)
C6	0.27967 (15)	0.59084 (8)	1.27155 (13)	0.0376 (3)
H6	0.299441	0.652439	1.305155	0.045*
C7	0.25478 (19)	0.54494 (9)	1.53231 (14)	0.0424 (3)
H7	0.273358	0.60689	1.564115	0.051*
C8	0.1668 (2)	0.24460 (10)	1.21046 (17)	0.0577 (4)
H8A	0.145807	0.186668	1.154094	0.086*
H8B	0.287788	0.240337	1.297763	0.086*
H8C	0.05098	0.257453	1.247879	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0671 (5)	0.0406 (5)	0.0279 (5)	−0.0002 (3)	0.0184 (4)	−0.0015 (3)
O2	0.0823 (6)	0.0336 (5)	0.0392 (6)	−0.0058 (4)	0.0229 (5)	−0.0032 (3)
O3	0.0749 (6)	0.0513 (6)	0.0302 (5)	−0.0034 (4)	0.0214 (4)	−0.0005 (3)
O4	0.1106 (9)	0.0351 (6)	0.0529 (7)	−0.0071 (5)	0.0268 (6)	0.0028 (4)
O5	0.0838 (7)	0.0512 (6)	0.0326 (6)	−0.0033 (4)	0.0223 (5)	0.0063 (4)
N1	0.0540 (5)	0.0378 (6)	0.0353 (6)	−0.0005 (4)	0.0135 (4)	0.0052 (4)
C1	0.0423 (5)	0.0336 (6)	0.0304 (6)	0.0017 (4)	0.0112 (4)	0.0029 (4)
C2	0.0415 (5)	0.0366 (6)	0.0274 (6)	0.0017 (4)	0.0120 (4)	0.0014 (4)
C3	0.0481 (5)	0.0335 (7)	0.0318 (6)	−0.0002 (4)	0.0126 (4)	0.0002 (4)
C4	0.0517 (6)	0.0353 (6)	0.0316 (6)	−0.0014 (4)	0.0163 (5)	0.0022 (4)
C5	0.0453 (6)	0.0396 (7)	0.0296 (6)	0.0012 (4)	0.0131 (4)	−0.0015 (4)
C6	0.0469 (6)	0.0340 (6)	0.0325 (7)	0.0010 (4)	0.0124 (5)	−0.0017 (4)
C7	0.0575 (6)	0.0407 (7)	0.0312 (6)	0.0001 (4)	0.0162 (5)	−0.0024 (4)
C8	0.0881 (9)	0.0352 (7)	0.0513 (8)	−0.0040 (6)	0.0225 (7)	0.0040 (5)

Geometric parameters (Å, º)

O1—C2	1.3271 (14)	C3—C4	1.3733 (16)
O1—H1	0.82	C4—C5	1.4080 (17)
O2—C3	1.3510 (15)	C4—H4	0.93
O2—C8	1.4310 (15)	C5—C6	1.3740 (15)
O3—C7	1.2068 (16)	C5—C7	1.4700 (16)
O4—N1	1.2097 (15)	C6—H6	0.93
O5—N1	1.2367 (15)	C7—H7	0.93
N1—C1	1.4520 (15)	C8—H8A	0.96
C1—C6	1.3998 (15)	C8—H8B	0.96
C1—C2	1.4008 (17)	C8—H8C	0.96
C2—C3	1.4270 (15)
C2—O1—H1	109.5	C5—C4—H4	119.7
C3—O2—C8	116.83 (9)	C6—C5—C4	120.54 (10)
O4—N1—O5	122.31 (11)	C6—C5—C7	120.27 (11)
O4—N1—C1	119.11 (11)	C4—C5—C7	119.18 (11)
O5—N1—C1	118.58 (10)	C5—C6—C1	118.84 (11)
C6—C1—C2	122.25 (11)	C5—C6—H6	120.6
C6—C1—N1	117.22 (11)	C1—C6—H6	120.6
C2—C1—N1	120.52 (10)	O3—C7—C5	123.43 (12)
O1—C2—C1	127.16 (10)	O3—C7—H7	118.3
O1—C2—C3	115.39 (10)	C5—C7—H7	118.3
C1—C2—C3	117.46 (10)	O2—C8—H8A	109.5
O2—C3—C4	125.69 (11)	O2—C8—H8B	109.5
O2—C3—C2	114.08 (10)	H8A—C8—H8B	109.5
C4—C3—C2	120.22 (11)	O2—C8—H8C	109.5
C3—C4—C5	120.69 (11)	H8A—C8—H8C	109.5
C3—C4—H4	119.7	H8B—C8—H8C	109.5
O4—N1—C1—C6	1.36 (17)	O1—C2—C3—C4	179.72 (9)
O5—N1—C1—C6	−178.32 (10)	C1—C2—C3—C4	−0.22 (16)
O4—N1—C1—C2	−179.20 (11)	O2—C3—C4—C5	−178.50 (10)
O5—N1—C1—C2	1.12 (16)	C2—C3—C4—C5	−0.07 (17)
C6—C1—C2—O1	−179.40 (10)	C3—C4—C5—C6	0.07 (17)
N1—C1—C2—O1	1.19 (17)	C3—C4—C5—C7	179.82 (10)
C6—C1—C2—C3	0.52 (16)	C4—C5—C6—C1	0.22 (16)
N1—C1—C2—C3	−178.89 (8)	C7—C5—C6—C1	−179.52 (10)
C8—O2—C3—C4	−2.73 (18)	C2—C1—C6—C5	−0.53 (16)
C8—O2—C3—C2	178.76 (10)	N1—C1—C6—C5	178.90 (8)
O1—C2—C3—O2	−1.68 (14)	C6—C5—C7—O3	−179.85 (11)
C1—C2—C3—O2	178.39 (9)	C4—C5—C7—O3	0.40 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^i	0.82	2.12	2.6989 (12)	128
O1—H1···O5	0.82	1.94	2.6247 (14)	140
C7—H7···O4^ii	0.93	2.50	3.4018 (16)	163
C8—H8A···O3^iii	0.96	2.60	3.4733 (18)	152
C8—H8B···O4^iv	0.96	2.58	3.476 (2)	156

Symmetry codes: (i) x, y, z−1; (ii) x, −y+3/2, z+1/2; (iii) x, −y+1/2, z−1/2; (iv) −x+1, y−1/2, −z+5/2.