(E)-2,4,5-Trimethoxy­benzaldehyde oxime

The title compound, C₁₀H₁₃NO₄, which exists as the E isomer, crystallizes with two independent mol­ecules in the asymmetric unit. The bond lengths and angles in both mol­ecules are normal. The crystal structure is stabilized by inter­molecular O—H...O hydrogen bonds, which link the mol­ecules into cyclic tetra­mers.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.035
• wR factor = 0.106
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C10 H13 N O4

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(E)-2,4,5-Trimethoxybenzaldehyde oxime

Crystal data

C10H13NO4	Z = 4
Mr = 211.21	F(000) = 448
Triclinic, P1	Dx = 1.298 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4428 (1) Å	Cell parameters from 1528 reflections
b = 10.7189 (1) Å	θ = 2.4–22.4°
c = 14.0290 (2) Å	µ = 0.10 mm^−1
α = 87.583 (1)°	T = 293 K
β = 88.451 (1)°	Block, colorless
γ = 75.214 (1)°	0.36 × 0.30 × 0.22 mm
V = 1081.04 (2) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3805 independent reflections
Radiation source: fine-focus sealed tube	3079 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.965, Tmax = 0.978	k = −12→12
12599 measured reflections	l = −16→16

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)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0542P)^2 + 0.1378P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3805 reflections	Δρmax = 0.15 e Å^−3
272 parameters	Δρmin = −0.11 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0058 (13)

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
O1	0.23909 (16)	0.53280 (10)	0.20946 (8)	0.0714 (3)
O2	−0.28464 (15)	0.53983 (10)	0.42574 (8)	0.0684 (3)
O3	−0.25307 (18)	0.82962 (12)	0.66363 (8)	0.0877 (4)
H3A	−0.2040	0.8654	0.7021	0.131*
O4	0.32536 (14)	0.70961 (10)	0.30188 (7)	0.0669 (3)
O5	0.45656 (15)	1.38071 (10)	0.87482 (8)	0.0751 (3)
H5A	0.5404	1.3822	0.8360	0.113*
O6	−0.07741 (15)	1.28758 (11)	1.01755 (8)	0.0744 (3)
O7	−0.21573 (14)	0.95086 (10)	0.83293 (7)	0.0685 (3)
O8	0.05978 (15)	0.95249 (10)	0.72070 (8)	0.0719 (3)
N1	−0.13484 (19)	0.79793 (12)	0.58378 (9)	0.0673 (3)
N2	0.36896 (17)	1.28563 (11)	0.85149 (9)	0.0614 (3)
C1	−0.08491 (19)	0.67322 (12)	0.44599 (10)	0.0521 (3)
C2	−0.13221 (19)	0.57914 (12)	0.39329 (10)	0.0534 (3)
C3	−0.0261 (2)	0.53020 (13)	0.31383 (10)	0.0561 (4)
H3B	−0.0582	0.4672	0.2792	0.067*
C4	0.1262 (2)	0.57440 (13)	0.28594 (10)	0.0547 (3)
C5	0.17403 (19)	0.67067 (13)	0.33734 (10)	0.0534 (3)
C6	0.06951 (19)	0.71753 (13)	0.41549 (10)	0.0532 (3)
H6A	0.1017	0.7809	0.4496	0.064*
C7	0.2067 (3)	0.43219 (17)	0.15608 (13)	0.0851 (5)
H7A	0.2968	0.4133	0.1050	0.128*
H7B	0.0841	0.4584	0.1302	0.128*
H7C	0.2171	0.3565	0.1968	0.128*
C8	−0.3396 (2)	0.44414 (16)	0.37522 (13)	0.0767 (5)
H8A	−0.4475	0.4259	0.4058	0.115*
H8B	−0.2402	0.3668	0.3749	0.115*
H8C	−0.3683	0.4750	0.3108	0.115*
C9	0.3825 (2)	0.80356 (16)	0.35333 (13)	0.0743 (5)
H9A	0.4886	0.8233	0.3219	0.111*
H9B	0.4147	0.7704	0.4170	0.111*
H9C	0.2828	0.8805	0.3560	0.111*
C10	−0.1882 (2)	0.72105 (14)	0.53203 (10)	0.0603 (4)
H10A	−0.2947	0.6948	0.5492	0.072*
C11	0.10658 (18)	1.20356 (13)	0.88569 (9)	0.0517 (3)
C12	−0.04554 (19)	1.20229 (13)	0.94502 (10)	0.0548 (3)
C13	−0.15600 (19)	1.11856 (13)	0.92964 (10)	0.0562 (3)
H13A	−0.2572	1.1181	0.9699	0.067*
C14	−0.11571 (19)	1.03619 (13)	0.85480 (10)	0.0540 (3)
C15	0.03646 (19)	1.03652 (13)	0.79381 (10)	0.0543 (3)
C16	0.14478 (19)	1.11883 (13)	0.80975 (10)	0.0538 (3)
H16A	0.2461	1.1187	0.7694	0.065*
C17	−0.3738 (2)	0.94619 (16)	0.88956 (12)	0.0688 (4)
H17A	−0.4307	0.8831	0.8656	0.103*
H17B	−0.4611	1.0294	0.8873	0.103*
H17C	−0.3372	0.9228	0.9543	0.103*
C18	0.2106 (2)	0.94858 (17)	0.65644 (12)	0.0784 (5)
H18A	0.2114	0.8867	0.6088	0.118*
H18B	0.3250	0.9241	0.6907	0.118*
H18C	0.1978	1.0323	0.6262	0.118*
C19	−0.2338 (3)	1.29425 (17)	1.07812 (12)	0.0799 (5)
H19A	−0.2388	1.3578	1.1250	0.120*
H19B	−0.2244	1.2116	1.1096	0.120*
H19C	−0.3447	1.3178	1.0410	0.120*
C20	0.2216 (2)	1.29233 (13)	0.90017 (10)	0.0574 (3)
H20A	0.1861	1.3548	0.9458	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0785 (7)	0.0749 (7)	0.0666 (7)	−0.0280 (5)	0.0117 (5)	−0.0234 (5)
O2	0.0684 (7)	0.0716 (6)	0.0743 (7)	−0.0334 (5)	0.0032 (5)	−0.0119 (5)
O3	0.1007 (9)	0.1009 (9)	0.0711 (8)	−0.0413 (7)	0.0224 (6)	−0.0313 (6)
O4	0.0692 (6)	0.0722 (6)	0.0674 (7)	−0.0322 (5)	0.0070 (5)	−0.0136 (5)
O5	0.0758 (7)	0.0735 (7)	0.0845 (8)	−0.0332 (6)	0.0078 (6)	−0.0170 (6)
O6	0.0785 (7)	0.0868 (7)	0.0632 (7)	−0.0277 (6)	0.0178 (5)	−0.0333 (6)
O7	0.0691 (7)	0.0759 (7)	0.0681 (7)	−0.0307 (5)	0.0150 (5)	−0.0224 (5)
O8	0.0769 (7)	0.0809 (7)	0.0649 (7)	−0.0306 (6)	0.0205 (5)	−0.0315 (5)
N1	0.0783 (9)	0.0682 (8)	0.0585 (8)	−0.0238 (6)	0.0100 (6)	−0.0138 (6)
N2	0.0610 (7)	0.0590 (7)	0.0666 (8)	−0.0187 (6)	0.0001 (6)	−0.0095 (6)
C1	0.0562 (8)	0.0511 (7)	0.0495 (8)	−0.0139 (6)	−0.0078 (6)	−0.0007 (6)
C2	0.0559 (8)	0.0509 (7)	0.0549 (8)	−0.0164 (6)	−0.0088 (6)	0.0025 (6)
C3	0.0650 (9)	0.0501 (7)	0.0564 (8)	−0.0188 (6)	−0.0086 (7)	−0.0079 (6)
C4	0.0607 (8)	0.0521 (7)	0.0507 (8)	−0.0127 (6)	−0.0039 (6)	−0.0044 (6)
C5	0.0553 (8)	0.0526 (7)	0.0538 (8)	−0.0163 (6)	−0.0055 (6)	0.0011 (6)
C6	0.0607 (8)	0.0513 (7)	0.0507 (8)	−0.0184 (6)	−0.0080 (6)	−0.0051 (6)
C7	0.0970 (13)	0.0802 (11)	0.0828 (12)	−0.0274 (10)	0.0125 (10)	−0.0352 (9)
C8	0.0742 (10)	0.0722 (10)	0.0940 (13)	−0.0358 (8)	−0.0065 (9)	−0.0101 (9)
C9	0.0771 (11)	0.0763 (10)	0.0804 (11)	−0.0380 (9)	0.0052 (8)	−0.0165 (8)
C10	0.0617 (9)	0.0654 (9)	0.0582 (9)	−0.0234 (7)	−0.0019 (7)	−0.0057 (7)
C11	0.0521 (8)	0.0549 (7)	0.0458 (7)	−0.0087 (6)	−0.0037 (6)	−0.0049 (6)
C12	0.0578 (8)	0.0576 (8)	0.0458 (8)	−0.0074 (6)	−0.0010 (6)	−0.0091 (6)
C13	0.0528 (8)	0.0638 (8)	0.0500 (8)	−0.0107 (6)	0.0060 (6)	−0.0081 (6)
C14	0.0539 (8)	0.0561 (8)	0.0513 (8)	−0.0121 (6)	−0.0007 (6)	−0.0060 (6)
C15	0.0576 (8)	0.0570 (8)	0.0467 (8)	−0.0104 (6)	0.0026 (6)	−0.0124 (6)
C16	0.0501 (8)	0.0613 (8)	0.0480 (8)	−0.0103 (6)	0.0046 (6)	−0.0070 (6)
C17	0.0624 (9)	0.0731 (10)	0.0738 (10)	−0.0225 (8)	0.0109 (8)	−0.0096 (8)
C18	0.0836 (11)	0.0821 (11)	0.0716 (11)	−0.0235 (9)	0.0262 (9)	−0.0299 (9)
C19	0.0876 (12)	0.0836 (11)	0.0673 (10)	−0.0180 (9)	0.0226 (9)	−0.0280 (9)
C20	0.0618 (9)	0.0579 (8)	0.0511 (8)	−0.0117 (6)	−0.0010 (7)	−0.0093 (6)

Geometric parameters (Å, º)

O1—C4	1.3625 (17)	C7—H7B	0.9600
O1—C7	1.4117 (18)	C7—H7C	0.9600
O2—C2	1.3681 (17)	C8—H8A	0.9600
O2—C8	1.4187 (17)	C8—H8B	0.9600
O3—N1	1.4039 (16)	C8—H8C	0.9600
O3—H3A	0.8200	C9—H9A	0.9600
O4—C5	1.3721 (17)	C9—H9B	0.9600
O4—C9	1.4186 (17)	C9—H9C	0.9600
O5—N2	1.3964 (15)	C10—H10A	0.9300
O5—H5A	0.8200	C11—C12	1.3896 (19)
O6—C12	1.3719 (16)	C11—C16	1.4050 (18)
O6—C19	1.4114 (19)	C11—C20	1.4563 (19)
O7—C14	1.3669 (17)	C12—C13	1.389 (2)
O7—C17	1.4124 (17)	C13—C14	1.3775 (19)
O8—C15	1.3718 (16)	C13—H13A	0.9300
O8—C18	1.4137 (18)	C14—C15	1.402 (2)
N1—C10	1.2636 (18)	C15—C16	1.3667 (19)
N2—C20	1.2642 (18)	C16—H16A	0.9300
C1—C2	1.3949 (18)	C17—H17A	0.9600
C1—C6	1.4016 (19)	C17—H17B	0.9600
C1—C10	1.453 (2)	C17—H17C	0.9600
C2—C3	1.390 (2)	C18—H18A	0.9600
C3—C4	1.378 (2)	C18—H18B	0.9600
C3—H3B	0.9300	C18—H18C	0.9600
C4—C5	1.4056 (19)	C19—H19A	0.9600
C5—C6	1.364 (2)	C19—H19B	0.9600
C6—H6A	0.9300	C19—H19C	0.9600
C7—H7A	0.9600	C20—H20A	0.9300
C4—O1—C7	118.94 (13)	H9A—C9—H9C	109.5
C2—O2—C8	118.43 (12)	H9B—C9—H9C	109.5
N1—O3—H3A	109.5	N1—C10—C1	120.78 (14)
C5—O4—C9	116.97 (11)	N1—C10—H10A	119.6
N2—O5—H5A	109.5	C1—C10—H10A	119.6
C12—O6—C19	118.65 (12)	C12—C11—C16	118.35 (13)
C14—O7—C17	118.66 (11)	C12—C11—C20	121.07 (12)
C15—O8—C18	117.58 (12)	C16—C11—C20	120.56 (13)
C10—N1—O3	111.06 (13)	O6—C12—C13	123.45 (13)
C20—N2—O5	111.93 (12)	O6—C12—C11	115.97 (13)
C2—C1—C6	118.12 (13)	C13—C12—C11	120.58 (12)
C2—C1—C10	121.22 (13)	C14—C13—C12	120.05 (13)
C6—C1—C10	120.63 (12)	C14—C13—H13A	120.0
O2—C2—C3	123.94 (12)	C12—C13—H13A	120.0
O2—C2—C1	115.77 (13)	O7—C14—C13	124.81 (13)
C3—C2—C1	120.29 (13)	O7—C14—C15	114.94 (12)
C4—C3—C2	120.45 (12)	C13—C14—C15	120.25 (13)
C4—C3—H3B	119.8	C16—C15—O8	125.86 (13)
C2—C3—H3B	119.8	C16—C15—C14	119.29 (12)
O1—C4—C3	125.05 (12)	O8—C15—C14	114.85 (12)
O1—C4—C5	114.96 (13)	C15—C16—C11	121.48 (13)
C3—C4—C5	119.99 (13)	C15—C16—H16A	119.3
C6—C5—O4	125.92 (12)	C11—C16—H16A	119.3
C6—C5—C4	119.06 (13)	O7—C17—H17A	109.5
O4—C5—C4	115.02 (12)	O7—C17—H17B	109.5
C5—C6—C1	122.09 (13)	H17A—C17—H17B	109.5
C5—C6—H6A	119.0	O7—C17—H17C	109.5
C1—C6—H6A	119.0	H17A—C17—H17C	109.5
O1—C7—H7A	109.5	H17B—C17—H17C	109.5
O1—C7—H7B	109.5	O8—C18—H18A	109.5
H7A—C7—H7B	109.5	O8—C18—H18B	109.5
O1—C7—H7C	109.5	H18A—C18—H18B	109.5
H7A—C7—H7C	109.5	O8—C18—H18C	109.5
H7B—C7—H7C	109.5	H18A—C18—H18C	109.5
O2—C8—H8A	109.5	H18B—C18—H18C	109.5
O2—C8—H8B	109.5	O6—C19—H19A	109.5
H8A—C8—H8B	109.5	O6—C19—H19B	109.5
O2—C8—H8C	109.5	H19A—C19—H19B	109.5
H8A—C8—H8C	109.5	O6—C19—H19C	109.5
H8B—C8—H8C	109.5	H19A—C19—H19C	109.5
O4—C9—H9A	109.5	H19B—C19—H19C	109.5
O4—C9—H9B	109.5	N2—C20—C11	120.87 (13)
H9A—C9—H9B	109.5	N2—C20—H20A	119.6
O4—C9—H9C	109.5	C11—C20—H20A	119.6
C8—O2—C2—C3	−0.5 (2)	C19—O6—C12—C13	−2.2 (2)
C8—O2—C2—C1	−179.91 (13)	C19—O6—C12—C11	177.70 (13)
C6—C1—C2—O2	−179.61 (11)	C16—C11—C12—O6	−179.51 (12)
C10—C1—C2—O2	2.53 (19)	C20—C11—C12—O6	−0.88 (19)
C6—C1—C2—C3	0.98 (19)	C16—C11—C12—C13	0.4 (2)
C10—C1—C2—C3	−176.87 (12)	C20—C11—C12—C13	179.00 (12)
O2—C2—C3—C4	−179.66 (12)	O6—C12—C13—C14	179.58 (13)
C1—C2—C3—C4	−0.3 (2)	C11—C12—C13—C14	−0.3 (2)
C7—O1—C4—C3	−3.4 (2)	C17—O7—C14—C13	0.8 (2)
C7—O1—C4—C5	177.23 (14)	C17—O7—C14—C15	−178.66 (13)
C2—C3—C4—O1	179.92 (13)	C12—C13—C14—O7	−179.51 (13)
C2—C3—C4—C5	−0.7 (2)	C12—C13—C14—C15	−0.1 (2)
C9—O4—C5—C6	2.6 (2)	C18—O8—C15—C16	1.0 (2)
C9—O4—C5—C4	−177.95 (12)	C18—O8—C15—C14	179.79 (13)
O1—C4—C5—C6	−179.54 (12)	O7—C14—C15—C16	179.85 (12)
C3—C4—C5—C6	1.0 (2)	C13—C14—C15—C16	0.4 (2)
O1—C4—C5—O4	0.97 (17)	O7—C14—C15—O8	0.94 (18)
C3—C4—C5—O4	−178.45 (12)	C13—C14—C15—O8	−178.54 (12)
O4—C5—C6—C1	179.09 (12)	O8—C15—C16—C11	178.50 (13)
C4—C5—C6—C1	−0.3 (2)	C14—C15—C16—C11	−0.3 (2)
C2—C1—C6—C5	−0.7 (2)	C12—C11—C16—C15	−0.1 (2)
C10—C1—C6—C5	177.21 (13)	C20—C11—C16—C15	−178.72 (13)
O3—N1—C10—C1	−179.00 (12)	O5—N2—C20—C11	178.73 (11)
C2—C1—C10—N1	173.87 (14)	C12—C11—C20—N2	173.75 (13)
C6—C1—C10—N1	−3.9 (2)	C16—C11—C20—N2	−7.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1^i	0.82	2.14	2.8676 (15)	148
O5—H5A···O4^i	0.82	2.29	2.9832 (15)	142

Symmetry code: (i) −x+1, −y+2, −z+1.