Different mol­ecular conformations in the crystal structures of three 5-nitro­imidazolyl derivatives

The title compounds show different conformations in the solid state.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.047
• wR factor = 0.126
• Data-to-parameter ratio = 15.6

Structure: II

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.094
• Data-to-parameter ratio = 15.6

Structure: III

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.051
• wR factor = 0.140
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5       ..O3               2.65 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report

Alert level G
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             107.6 Degree
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 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
   2 ALERT level G = General information/check it is not something unexpected

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




Datablock: II


Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for   O3       --N4        .        6.2 s.u.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5       ..O2               2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4C      ..F1               2.77 Ang.

Alert level G
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             107.9 Degree
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 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
   4 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
   1 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




Datablock: III



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9       ..N1               2.77 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5       ..O2               2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A      ..O2               2.63 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.454 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         15 Report
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.87A   From Br1             1.90 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.94A   From Br1             1.80 eA-3
PLAT975_ALERT_2_C Check Calcd Resid. Dens.  0.84A   From O1              0.42 eA-3
PLAT977_ALERT_2_C Check Negative Difference Density on H5               -0.39 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.66 mm
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             108.3 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          9 Note
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  10 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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

For all structures, data collection: CrystalClear (Rigaku, 2012); cell refinement: CrystalClear (Rigaku, 2012); data reduction: CrystalClear (Rigaku, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

(E)-1-Methyl-5-nitro-1H-imidazole-2-carbaldehyde O-benzyloxime (I)

Crystal data

C12H12N4O3	F(000) = 544
Mr = 260.26	Dx = 1.457 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.6399 (5) Å	Cell parameters from 7971 reflections
b = 10.5071 (7) Å	θ = 2.4–27.5°
c = 14.9243 (11) Å	µ = 0.11 mm^−1
β = 97.942 (3)°	T = 100 K
V = 1186.53 (14) Å^3	Plate, colourless
Z = 4	0.11 × 0.07 × 0.03 mm

Data collection

Rigaku Saturn724+ CCD diffractometer	1891 reflections with I > 2σ(I)
ω scans	Rint = 0.055
Absorption correction: multi-scan (FS_ABSCOR; Rigaku, 2013)	θmax = 27.5°, θmin = 2.4°
Tmin = 0.618, Tmax = 1.000	h = −9→6
7757 measured reflections	k = −13→13
2705 independent reflections	l = −19→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.0674P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max < 0.001
2705 reflections	Δρmax = 0.24 e Å^−3
173 parameters	Δρmin = −0.22 e Å^−3
0 restraints

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
C1	−0.2026 (2)	0.18424 (17)	0.08287 (11)	0.0272 (4)
C2	−0.1242 (2)	0.06989 (17)	0.10516 (11)	0.0302 (4)
H2	−0.1177	0.0010	0.0646	0.036*
C3	−0.0953 (2)	0.18453 (17)	0.22478 (11)	0.0262 (4)
C4	−0.2593 (2)	0.38590 (16)	0.17211 (11)	0.0295 (4)
H4A	−0.3780	0.3918	0.1378	0.044*
H4B	−0.1832	0.4512	0.1508	0.044*
H4C	−0.2661	0.3991	0.2365	0.044*
C5	−0.0422 (2)	0.23260 (16)	0.31595 (11)	0.0277 (4)
H5	−0.0610	0.3193	0.3300	0.033*
C6	0.1846 (3)	0.13647 (17)	0.51983 (12)	0.0353 (5)
H6A	0.2794	0.0969	0.4903	0.042*
H6B	0.1069	0.0680	0.5372	0.042*
C7	0.2641 (2)	0.20824 (16)	0.60261 (11)	0.0275 (4)
C8	0.2637 (2)	0.15343 (17)	0.68727 (11)	0.0296 (4)
H8	0.2039	0.0751	0.6927	0.036*
C9	0.3508 (2)	0.21295 (18)	0.76444 (12)	0.0328 (4)
H9	0.3522	0.1739	0.8220	0.039*
C10	0.4346 (2)	0.32796 (18)	0.75770 (12)	0.0336 (4)
H10	0.4943	0.3680	0.8103	0.040*
C11	0.4313 (2)	0.38490 (17)	0.67342 (12)	0.0327 (4)
H11	0.4865	0.4652	0.6686	0.039*
C12	0.3475 (2)	0.32503 (17)	0.59602 (11)	0.0293 (4)
H12	0.3471	0.3639	0.5385	0.035*
N1	−0.05705 (18)	0.06958 (14)	0.19410 (9)	0.0292 (4)
N2	−0.18520 (17)	0.25946 (13)	0.15896 (9)	0.0257 (3)
N3	0.03028 (18)	0.15619 (14)	0.37682 (9)	0.0287 (3)
N4	−0.28663 (19)	0.22404 (14)	−0.00435 (9)	0.0308 (4)
O1	0.08352 (16)	0.22291 (11)	0.45775 (7)	0.0304 (3)
O2	−0.33264 (17)	0.33549 (12)	−0.01644 (8)	0.0382 (3)
O3	−0.30669 (18)	0.14106 (13)	−0.06357 (8)	0.0402 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0262 (8)	0.0346 (9)	0.0192 (8)	−0.0040 (7)	−0.0031 (6)	0.0003 (7)
C2	0.0309 (9)	0.0354 (9)	0.0224 (9)	−0.0024 (8)	−0.0026 (7)	−0.0007 (7)
C3	0.0231 (8)	0.0319 (9)	0.0215 (8)	−0.0024 (7)	−0.0038 (6)	0.0032 (7)
C4	0.0303 (9)	0.0299 (8)	0.0257 (9)	0.0015 (7)	−0.0055 (7)	0.0003 (7)
C5	0.0276 (9)	0.0319 (8)	0.0215 (8)	−0.0012 (7)	−0.0033 (7)	0.0000 (7)
C6	0.0412 (10)	0.0328 (9)	0.0270 (9)	0.0019 (8)	−0.0131 (8)	0.0024 (8)
C7	0.0243 (8)	0.0320 (9)	0.0232 (8)	0.0031 (7)	−0.0070 (6)	0.0001 (7)
C8	0.0266 (8)	0.0335 (9)	0.0272 (9)	0.0006 (7)	−0.0018 (7)	0.0034 (7)
C9	0.0328 (9)	0.0427 (10)	0.0211 (9)	0.0104 (8)	−0.0030 (7)	0.0024 (8)
C10	0.0305 (9)	0.0404 (10)	0.0263 (9)	0.0069 (8)	−0.0090 (7)	−0.0072 (8)
C11	0.0271 (9)	0.0317 (9)	0.0366 (10)	−0.0005 (7)	−0.0049 (7)	−0.0031 (8)
C12	0.0285 (9)	0.0344 (9)	0.0230 (9)	0.0024 (8)	−0.0031 (7)	0.0037 (7)
N1	0.0306 (7)	0.0339 (8)	0.0212 (7)	−0.0019 (6)	−0.0033 (6)	0.0012 (6)
N2	0.0247 (7)	0.0305 (7)	0.0197 (7)	−0.0012 (6)	−0.0049 (6)	0.0002 (6)
N3	0.0282 (7)	0.0355 (8)	0.0203 (7)	−0.0027 (6)	−0.0040 (6)	−0.0042 (6)
N4	0.0321 (8)	0.0374 (8)	0.0202 (7)	−0.0036 (7)	−0.0054 (6)	0.0002 (7)
O1	0.0334 (7)	0.0358 (6)	0.0185 (6)	0.0028 (5)	−0.0087 (5)	−0.0025 (5)
O2	0.0460 (8)	0.0378 (7)	0.0271 (7)	0.0049 (6)	−0.0085 (6)	0.0048 (6)
O3	0.0500 (8)	0.0428 (7)	0.0236 (7)	−0.0058 (6)	−0.0097 (6)	−0.0054 (6)

Geometric parameters (Å, º)

C1—C2	1.363 (2)	C6—H6A	0.9900
C1—N2	1.375 (2)	C6—H6B	0.9900
C1—N4	1.432 (2)	C7—C8	1.389 (2)
C2—N1	1.355 (2)	C7—C12	1.392 (2)
C2—H2	0.9500	C8—C9	1.396 (2)
C3—N1	1.338 (2)	C8—H8	0.9500
C3—N2	1.368 (2)	C9—C10	1.378 (3)
C3—C5	1.456 (2)	C9—H9	0.9500
C4—N2	1.468 (2)	C10—C11	1.390 (3)
C4—H4A	0.9800	C10—H10	0.9500
C4—H4B	0.9800	C11—C12	1.391 (2)
C4—H4C	0.9800	C11—H11	0.9500
C5—N3	1.279 (2)	C12—H12	0.9500
C5—H5	0.9500	N3—O1	1.4071 (16)
C6—O1	1.4428 (19)	N4—O2	1.2287 (18)
C6—C7	1.502 (2)	N4—O3	1.2359 (18)
C2—C1—N2	108.43 (14)	C12—C7—C6	121.42 (15)
C2—C1—N4	127.30 (16)	C7—C8—C9	120.27 (17)
N2—C1—N4	124.26 (15)	C7—C8—H8	119.9
N1—C2—C1	109.59 (15)	C9—C8—H8	119.9
N1—C2—H2	125.2	C10—C9—C8	120.40 (16)
C1—C2—H2	125.2	C10—C9—H9	119.8
N1—C3—N2	112.68 (14)	C8—C9—H9	119.8
N1—C3—C5	125.95 (14)	C9—C10—C11	119.54 (16)
N2—C3—C5	121.28 (15)	C9—C10—H10	120.2
N2—C4—H4A	109.5	C11—C10—H10	120.2
N2—C4—H4B	109.5	C10—C11—C12	120.36 (17)
H4A—C4—H4B	109.5	C10—C11—H11	119.8
N2—C4—H4C	109.5	C12—C11—H11	119.8
H4A—C4—H4C	109.5	C11—C12—C7	120.16 (16)
H4B—C4—H4C	109.5	C11—C12—H12	119.9
N3—C5—C3	118.90 (15)	C7—C12—H12	119.9
N3—C5—H5	120.5	C3—N1—C2	105.18 (14)
C3—C5—H5	120.5	C3—N2—C1	104.12 (14)
O1—C6—C7	109.39 (14)	C3—N2—C4	126.14 (14)
O1—C6—H6A	109.8	C1—N2—C4	129.47 (13)
C7—C6—H6A	109.8	C5—N3—O1	110.01 (13)
O1—C6—H6B	109.8	O2—N4—O3	124.23 (14)
C7—C6—H6B	109.8	O2—N4—C1	119.68 (14)
H6A—C6—H6B	108.2	O3—N4—C1	116.09 (14)
C8—C7—C12	119.23 (15)	N3—O1—C6	107.65 (12)
C8—C7—C6	119.24 (16)
N2—C1—C2—N1	0.2 (2)	C1—C2—N1—C3	−0.16 (19)
N4—C1—C2—N1	178.92 (15)	N1—C3—N2—C1	0.01 (19)
N1—C3—C5—N3	−8.6 (3)	C5—C3—N2—C1	176.86 (15)
N2—C3—C5—N3	175.00 (15)	N1—C3—N2—C4	174.49 (15)
O1—C6—C7—C8	138.31 (16)	C5—C3—N2—C4	−8.7 (2)
O1—C6—C7—C12	−45.5 (2)	C2—C1—N2—C3	−0.11 (18)
C12—C7—C8—C9	−2.0 (3)	N4—C1—N2—C3	−178.90 (15)
C6—C7—C8—C9	174.21 (16)	C2—C1—N2—C4	−174.33 (16)
C7—C8—C9—C10	1.4 (3)	N4—C1—N2—C4	6.9 (3)
C8—C9—C10—C11	0.3 (3)	C3—C5—N3—O1	175.55 (14)
C9—C10—C11—C12	−1.5 (3)	C2—C1—N4—O2	−171.21 (18)
C10—C11—C12—C7	0.9 (3)	N2—C1—N4—O2	7.4 (3)
C8—C7—C12—C11	0.9 (3)	C2—C1—N4—O3	8.3 (3)
C6—C7—C12—C11	−175.28 (16)	N2—C1—N4—O3	−173.14 (16)
N2—C3—N1—C2	0.09 (19)	C5—N3—O1—C6	−172.50 (15)
C5—C3—N1—C2	−176.59 (16)	C7—C6—O1—N3	172.62 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···N3^i	0.98	2.51	3.466 (2)	165
C5—H5···O3^ii	0.95	2.65	3.175 (2)	115

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

(E)-1-Methyl-5-nitro-1H-imidazole-2-carbaldehyde O-(4-fluorobenzyl) oxime (II)

Crystal data

C12H11FN4O3	F(000) = 576
Mr = 278.25	Dx = 1.481 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.5484 (2) Å	Cell parameters from 7472 reflections
b = 12.6442 (4) Å	θ = 3.1–27.5°
c = 13.4150 (9) Å	µ = 0.12 mm^−1
β = 102.988 (7)°	T = 120 K
V = 1247.62 (10) Å^3	Block, orange
Z = 4	0.19 × 0.13 × 0.10 mm

Data collection

Rigaku Saturn724+ CCD diffractometer	2292 reflections with I > 2σ(I)
ω scans	Rint = 0.021
Absorption correction: multi-scan (FS_ABSCOR; Rigaku, 2013)	θmax = 27.5°, θmin = 3.1°
Tmin = 0.802, Tmax = 1.000	h = −9→9
8522 measured reflections	k = −14→16
2848 independent reflections	l = −14→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0501P)^2 + 0.1808P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2848 reflections	Δρmax = 0.29 e Å^−3
182 parameters	Δρmin = −0.18 e Å^−3
0 restraints

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
C1	0.40044 (15)	0.59196 (9)	0.16775 (9)	0.0177 (2)
C2	0.38559 (16)	0.48697 (9)	0.14129 (9)	0.0192 (3)
H2	0.3923	0.4590	0.0765	0.023*
C3	0.35720 (15)	0.49975 (9)	0.29626 (9)	0.0160 (2)
C4	0.40828 (17)	0.69554 (9)	0.33328 (9)	0.0213 (3)
H4A	0.3204	0.7499	0.3025	0.032*
H4B	0.5320	0.7228	0.3401	0.032*
H4C	0.3892	0.6769	0.4010	0.032*
C5	0.32784 (15)	0.46335 (9)	0.39394 (9)	0.0176 (2)
H5	0.3457	0.3906	0.4109	0.021*
C6	0.18665 (15)	0.54029 (9)	0.60895 (9)	0.0185 (2)
H6A	0.0718	0.5716	0.5697	0.022*
H6B	0.2737	0.5984	0.6330	0.022*
C7	0.15188 (14)	0.47943 (9)	0.69873 (9)	0.0175 (2)
C8	0.10500 (15)	0.37210 (9)	0.69078 (9)	0.0201 (3)
H8	0.1018	0.3354	0.6286	0.024*
C9	0.06311 (16)	0.31892 (10)	0.77312 (10)	0.0238 (3)
H9	0.0328	0.2459	0.7684	0.029*
C10	0.06662 (16)	0.37454 (11)	0.86169 (10)	0.0249 (3)
C11	0.11210 (17)	0.48020 (11)	0.87283 (9)	0.0250 (3)
H11	0.1132	0.5165	0.9350	0.030*
C12	0.15620 (16)	0.53179 (10)	0.79027 (9)	0.0210 (3)
H12	0.1900	0.6043	0.7965	0.025*
N1	0.36001 (13)	0.42969 (8)	0.22186 (7)	0.0187 (2)
N2	0.38326 (12)	0.60100 (7)	0.26758 (7)	0.0160 (2)
N3	0.27904 (12)	0.52518 (8)	0.45773 (7)	0.0180 (2)
N4	0.42710 (14)	0.67827 (8)	0.10515 (8)	0.0225 (2)
O1	0.26029 (11)	0.46915 (6)	0.54488 (6)	0.01878 (19)
O2	0.44180 (14)	0.76801 (7)	0.14148 (7)	0.0315 (2)
O3	0.43216 (14)	0.65795 (8)	0.01587 (7)	0.0338 (2)
F1	0.02098 (11)	0.32309 (7)	0.94206 (6)	0.0378 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0181 (5)	0.0188 (6)	0.0166 (6)	0.0022 (4)	0.0048 (4)	0.0022 (5)
C2	0.0219 (6)	0.0197 (6)	0.0162 (6)	0.0018 (4)	0.0051 (4)	−0.0009 (5)
C3	0.0138 (5)	0.0155 (5)	0.0181 (6)	0.0007 (4)	0.0022 (4)	0.0002 (5)
C4	0.0275 (6)	0.0157 (6)	0.0215 (6)	−0.0017 (4)	0.0071 (5)	−0.0037 (5)
C5	0.0177 (5)	0.0164 (6)	0.0184 (6)	−0.0011 (4)	0.0030 (4)	0.0005 (5)
C6	0.0188 (5)	0.0187 (6)	0.0185 (6)	0.0011 (4)	0.0055 (4)	−0.0031 (5)
C7	0.0121 (5)	0.0208 (6)	0.0189 (6)	0.0023 (4)	0.0022 (4)	0.0004 (5)
C8	0.0180 (5)	0.0211 (6)	0.0206 (6)	0.0016 (4)	0.0031 (4)	−0.0007 (5)
C9	0.0214 (6)	0.0211 (6)	0.0286 (7)	0.0017 (5)	0.0049 (5)	0.0053 (5)
C10	0.0212 (6)	0.0328 (7)	0.0217 (6)	0.0045 (5)	0.0067 (5)	0.0111 (5)
C11	0.0237 (6)	0.0342 (7)	0.0174 (6)	0.0031 (5)	0.0053 (5)	−0.0008 (5)
C12	0.0188 (6)	0.0221 (6)	0.0218 (6)	0.0010 (4)	0.0037 (4)	−0.0012 (5)
N1	0.0203 (5)	0.0175 (5)	0.0181 (5)	0.0003 (4)	0.0042 (4)	−0.0013 (4)
N2	0.0164 (4)	0.0146 (5)	0.0172 (5)	0.0012 (4)	0.0041 (4)	0.0005 (4)
N3	0.0170 (5)	0.0200 (5)	0.0167 (5)	−0.0001 (4)	0.0032 (4)	0.0030 (4)
N4	0.0237 (5)	0.0212 (5)	0.0243 (6)	0.0027 (4)	0.0092 (4)	0.0038 (4)
O1	0.0230 (4)	0.0186 (4)	0.0164 (4)	0.0026 (3)	0.0077 (3)	0.0022 (3)
O2	0.0468 (6)	0.0176 (5)	0.0332 (6)	−0.0032 (4)	0.0158 (4)	0.0013 (4)
O3	0.0537 (6)	0.0307 (5)	0.0217 (5)	0.0033 (4)	0.0182 (4)	0.0037 (4)
F1	0.0437 (5)	0.0446 (5)	0.0286 (4)	0.0027 (4)	0.0158 (4)	0.0162 (4)

Geometric parameters (Å, º)

C1—C2	1.3721 (16)	C6—H6A	0.9900
C1—N2	1.3789 (15)	C6—H6B	0.9900
C1—N4	1.4187 (15)	C7—C12	1.3890 (16)
C2—N1	1.3506 (15)	C7—C8	1.4005 (17)
C2—H2	0.9500	C8—C9	1.3890 (17)
C3—N1	1.3382 (15)	C8—H8	0.9500
C3—N2	1.3636 (15)	C9—C10	1.3757 (18)
C3—C5	1.4522 (16)	C9—H9	0.9500
C4—N2	1.4721 (15)	C10—F1	1.3679 (14)
C4—H4A	0.9800	C10—C11	1.3791 (19)
C4—H4B	0.9800	C11—C12	1.3888 (17)
C4—H4C	0.9800	C11—H11	0.9500
C5—N3	1.2731 (15)	C12—H12	0.9500
C5—H5	0.9500	N3—O1	1.4012 (12)
C6—O1	1.4393 (13)	N4—O2	1.2301 (14)
C6—C7	1.5013 (16)	N4—O3	1.2339 (14)
C2—C1—N2	108.14 (10)	C8—C7—C6	121.49 (11)
C2—C1—N4	127.25 (11)	C9—C8—C7	120.48 (11)
N2—C1—N4	124.60 (10)	C9—C8—H8	119.8
N1—C2—C1	109.26 (10)	C7—C8—H8	119.8
N1—C2—H2	125.4	C10—C9—C8	118.41 (12)
C1—C2—H2	125.4	C10—C9—H9	120.8
N1—C3—N2	112.56 (10)	C8—C9—H9	120.8
N1—C3—C5	119.63 (10)	F1—C10—C9	118.57 (12)
N2—C3—C5	127.81 (10)	F1—C10—C11	118.42 (12)
N2—C4—H4A	109.5	C9—C10—C11	123.01 (12)
N2—C4—H4B	109.5	C10—C11—C12	117.84 (12)
H4A—C4—H4B	109.5	C10—C11—H11	121.1
N2—C4—H4C	109.5	C12—C11—H11	121.1
H4A—C4—H4C	109.5	C11—C12—C7	121.26 (11)
H4B—C4—H4C	109.5	C11—C12—H12	119.4
N3—C5—C3	122.53 (11)	C7—C12—H12	119.4
N3—C5—H5	118.7	C3—N1—C2	105.71 (10)
C3—C5—H5	118.7	C3—N2—C1	104.31 (9)
O1—C6—C7	108.62 (9)	C3—N2—C4	126.92 (10)
O1—C6—H6A	110.0	C1—N2—C4	128.42 (10)
C7—C6—H6A	110.0	C5—N3—O1	110.43 (9)
O1—C6—H6B	110.0	O2—N4—O3	123.85 (11)
C7—C6—H6B	110.0	O2—N4—C1	119.16 (10)
H6A—C6—H6B	108.3	O3—N4—C1	116.99 (10)
C12—C7—C8	118.98 (11)	N3—O1—C6	107.89 (8)
C12—C7—C6	119.43 (10)
N2—C1—C2—N1	−0.16 (13)	C5—C3—N1—C2	178.73 (10)
N4—C1—C2—N1	−179.62 (11)	C1—C2—N1—C3	0.72 (13)
N1—C3—C5—N3	−162.10 (10)	N1—C3—N2—C1	0.95 (12)
N2—C3—C5—N3	17.64 (18)	C5—C3—N2—C1	−178.81 (11)
O1—C6—C7—C12	152.70 (10)	N1—C3—N2—C4	−172.71 (10)
O1—C6—C7—C8	−30.95 (14)	C5—C3—N2—C4	7.53 (18)
C12—C7—C8—C9	0.13 (16)	C2—C1—N2—C3	−0.46 (12)
C6—C7—C8—C9	−176.23 (10)	N4—C1—N2—C3	179.02 (10)
C7—C8—C9—C10	0.82 (17)	C2—C1—N2—C4	173.07 (10)
C8—C9—C10—F1	178.37 (10)	N4—C1—N2—C4	−7.45 (18)
C8—C9—C10—C11	−0.87 (18)	C3—C5—N3—O1	179.79 (9)
F1—C10—C11—C12	−179.30 (10)	C2—C1—N4—O2	−178.34 (11)
C9—C10—C11—C12	−0.05 (18)	N2—C1—N4—O2	2.29 (17)
C10—C11—C12—C7	1.06 (18)	C2—C1—N4—O3	2.41 (18)
C8—C7—C12—C11	−1.10 (17)	N2—C1—N4—O3	−176.96 (11)
C6—C7—C12—C11	175.34 (10)	C5—N3—O1—C6	−173.96 (9)
N2—C3—N1—C2	−1.05 (13)	C7—C6—O1—N3	175.61 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4C···N3	0.98	2.29	3.0184 (15)	131
C4—H4A···N1^i	0.98	2.63	3.5693 (16)	160
C9—H9···N1^ii	0.95	2.58	3.4973 (16)	163
C2—H2···O3^iii	0.95	2.49	3.3165 (15)	145
C5—H5···O2^iv	0.95	2.63	3.1676 (14)	116
C6—H6A···O2^v	0.99	2.54	3.1376 (14)	119
C4—H4C···F1^vi	0.98	2.77	3.353 (2)	119

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

(E)-1-Methyl-5-nitro-1H-imidazole-2-carbaldehyde O-(4-bromobenzyl) oxime (III)

Crystal data

C12H11BrN4O3	F(000) = 680
Mr = 339.16	Dx = 1.730 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.6024 (2) Å	Cell parameters from 6837 reflections
b = 12.7526 (3) Å	θ = 2.2–27.5°
c = 13.8954 (5) Å	µ = 3.17 mm^−1
β = 104.869 (2)°	T = 120 K
V = 1302.05 (7) Å^3	Block, yellow
Z = 4	0.66 × 0.52 × 0.24 mm

Data collection

Rigaku Mercury CCD diffractometer	2835 reflections with I > 2σ(I)
ω scans	Rint = 0.065
Absorption correction: multi-scan (FS_ABSCOR; Rigaku, 2013)	θmax = 27.5°, θmin = 2.2°
Tmin = 0.438, Tmax = 1.000	h = −8→9
16791 measured reflections	k = −16→16
2974 independent reflections	l = −18→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.140	w = 1/[σ^2(Fo^2) + (0.0837P)^2 + 1.3179P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.001
2974 reflections	Δρmax = 1.78 e Å^−3
182 parameters	Δρmin = −1.03 e Å^−3
0 restraints

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
C1	0.4010 (4)	0.5860 (2)	0.1628 (2)	0.0210 (6)
C2	0.3825 (4)	0.4812 (2)	0.1385 (2)	0.0227 (6)
H2	0.3902	0.4517	0.0769	0.027*
C3	0.3498 (4)	0.4984 (2)	0.2868 (2)	0.0201 (6)
C4	0.3974 (5)	0.6933 (2)	0.3184 (3)	0.0281 (7)
H4A	0.3108	0.7457	0.2827	0.042*
H4B	0.5214	0.7210	0.3308	0.042*
H4C	0.3704	0.6770	0.3821	0.042*
C5	0.3150 (4)	0.4652 (2)	0.3803 (2)	0.0221 (6)
H5	0.3120	0.3922	0.3932	0.026*
C6	0.2011 (4)	0.5460 (2)	0.5916 (2)	0.0227 (6)
H6A	0.0894	0.5833	0.5554	0.027*
H6B	0.2982	0.5986	0.6159	0.027*
C7	0.1655 (4)	0.4863 (2)	0.6778 (2)	0.0203 (6)
C8	0.1233 (4)	0.3798 (2)	0.6718 (2)	0.0229 (6)
H8	0.1207	0.3422	0.6124	0.027*
C9	0.0849 (4)	0.3284 (2)	0.7522 (2)	0.0237 (6)
H9	0.0561	0.2558	0.7481	0.028*
C10	0.0890 (4)	0.3840 (2)	0.8382 (2)	0.0224 (6)
C11	0.1292 (4)	0.4900 (2)	0.8463 (2)	0.0232 (6)
H11	0.1300	0.5275	0.9055	0.028*
C12	0.1683 (4)	0.5400 (2)	0.7656 (2)	0.0232 (6)
H12	0.1977	0.6126	0.7702	0.028*
N1	0.3517 (4)	0.42704 (18)	0.21619 (19)	0.0233 (5)
N2	0.3819 (3)	0.59752 (17)	0.25814 (18)	0.0191 (5)
N3	0.2882 (3)	0.52867 (18)	0.44583 (19)	0.0219 (5)
N4	0.4338 (4)	0.6687 (2)	0.1020 (2)	0.0234 (5)
O1	0.2561 (3)	0.47297 (15)	0.52654 (16)	0.0239 (5)
O2	0.4605 (4)	0.75804 (16)	0.13734 (19)	0.0325 (5)
O3	0.4324 (4)	0.64727 (19)	0.01529 (19)	0.0343 (6)
Br1	0.04121 (4)	0.31299 (2)	0.94938 (2)	0.02821 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0257 (14)	0.0171 (12)	0.0208 (14)	0.0008 (10)	0.0071 (11)	−0.0021 (10)
C2	0.0304 (15)	0.0168 (12)	0.0214 (15)	0.0020 (10)	0.0076 (12)	−0.0035 (10)
C3	0.0216 (13)	0.0147 (11)	0.0239 (15)	0.0002 (10)	0.0058 (11)	−0.0007 (10)
C4	0.0431 (19)	0.0137 (13)	0.0295 (18)	−0.0020 (11)	0.0132 (15)	−0.0045 (10)
C5	0.0241 (14)	0.0144 (11)	0.0284 (16)	0.0010 (10)	0.0078 (12)	0.0019 (10)
C6	0.0284 (15)	0.0165 (12)	0.0237 (15)	0.0008 (10)	0.0079 (12)	0.0004 (10)
C7	0.0198 (13)	0.0173 (12)	0.0231 (15)	0.0017 (10)	0.0042 (11)	0.0025 (10)
C8	0.0259 (14)	0.0168 (12)	0.0256 (15)	0.0013 (10)	0.0058 (11)	−0.0016 (10)
C9	0.0279 (15)	0.0140 (11)	0.0291 (17)	0.0004 (10)	0.0072 (12)	0.0008 (11)
C10	0.0218 (14)	0.0196 (13)	0.0262 (15)	0.0019 (10)	0.0069 (11)	0.0052 (10)
C11	0.0275 (15)	0.0202 (13)	0.0221 (15)	0.0010 (11)	0.0067 (12)	−0.0016 (10)
C12	0.0290 (15)	0.0141 (12)	0.0269 (16)	−0.0015 (10)	0.0082 (12)	0.0000 (10)
N1	0.0305 (13)	0.0144 (10)	0.0255 (13)	−0.0002 (9)	0.0083 (10)	−0.0035 (9)
N2	0.0261 (12)	0.0126 (10)	0.0195 (12)	−0.0001 (8)	0.0071 (9)	−0.0015 (9)
N3	0.0263 (12)	0.0176 (10)	0.0227 (13)	−0.0007 (9)	0.0079 (10)	0.0041 (9)
N4	0.0268 (13)	0.0188 (11)	0.0257 (14)	0.0005 (9)	0.0090 (11)	0.0011 (10)
O1	0.0328 (12)	0.0170 (9)	0.0253 (12)	0.0019 (8)	0.0137 (9)	0.0027 (8)
O2	0.0485 (14)	0.0161 (10)	0.0357 (13)	−0.0055 (9)	0.0158 (11)	−0.0015 (9)
O3	0.0536 (15)	0.0290 (12)	0.0251 (13)	0.0010 (11)	0.0190 (11)	−0.0004 (10)
Br1	0.0366 (2)	0.0231 (2)	0.0267 (2)	0.00051 (10)	0.01133 (17)	0.00691 (10)

Geometric parameters (Å, º)

C1—C2	1.377 (4)	C6—H6A	0.9900
C1—N2	1.378 (4)	C6—H6B	0.9900
C1—N4	1.413 (4)	C7—C8	1.393 (4)
C2—N1	1.352 (4)	C7—C12	1.394 (4)
C2—H2	0.9500	C8—C9	1.389 (4)
C3—N1	1.341 (4)	C8—H8	0.9500
C3—N2	1.366 (3)	C9—C10	1.383 (4)
C3—C5	1.453 (4)	C9—H9	0.9500
C4—N2	1.468 (3)	C10—C11	1.384 (4)
C4—H4A	0.9800	C10—Br1	1.905 (3)
C4—H4B	0.9800	C11—C12	1.387 (4)
C4—H4C	0.9800	C11—H11	0.9500
C5—N3	1.273 (4)	C12—H12	0.9500
C5—H5	0.9500	N3—O1	1.401 (3)
C6—O1	1.433 (4)	N4—O3	1.232 (4)
C6—C7	1.502 (4)	N4—O2	1.237 (3)
C2—C1—N2	108.0 (3)	C12—C7—C6	118.9 (2)
C2—C1—N4	126.9 (3)	C9—C8—C7	120.3 (3)
N2—C1—N4	125.1 (2)	C9—C8—H8	119.8
N1—C2—C1	109.1 (3)	C7—C8—H8	119.8
N1—C2—H2	125.4	C10—C9—C8	119.4 (3)
C1—C2—H2	125.4	C10—C9—H9	120.3
N1—C3—N2	112.2 (3)	C8—C9—H9	120.3
N1—C3—C5	119.7 (2)	C9—C10—C11	121.8 (3)
N2—C3—C5	128.1 (3)	C9—C10—Br1	119.4 (2)
N2—C4—H4A	109.5	C11—C10—Br1	118.8 (2)
N2—C4—H4B	109.5	C10—C11—C12	118.1 (3)
H4A—C4—H4B	109.5	C10—C11—H11	120.9
N2—C4—H4C	109.5	C12—C11—H11	120.9
H4A—C4—H4C	109.5	C11—C12—C7	121.5 (3)
H4B—C4—H4C	109.5	C11—C12—H12	119.2
N3—C5—C3	123.6 (3)	C7—C12—H12	119.2
N3—C5—H5	118.2	C3—N1—C2	105.9 (2)
C3—C5—H5	118.2	C3—N2—C1	104.7 (2)
O1—C6—C7	108.3 (2)	C3—N2—C4	126.7 (3)
O1—C6—H6A	110.0	C1—N2—C4	128.6 (2)
C7—C6—H6A	110.0	C5—N3—O1	110.1 (2)
O1—C6—H6B	110.0	O3—N4—O2	123.5 (3)
C7—C6—H6B	110.0	O3—N4—C1	117.4 (2)
H6A—C6—H6B	108.4	O2—N4—C1	119.1 (3)
C8—C7—C12	118.9 (3)	N3—O1—C6	108.3 (2)
C8—C7—C6	122.2 (3)
N2—C1—C2—N1	0.2 (3)	C5—C3—N1—C2	178.5 (3)
N4—C1—C2—N1	−179.8 (3)	C1—C2—N1—C3	0.5 (3)
N1—C3—C5—N3	−170.9 (3)	N1—C3—N2—C1	1.3 (3)
N2—C3—C5—N3	8.7 (5)	C5—C3—N2—C1	−178.3 (3)
O1—C6—C7—C8	−23.1 (4)	N1—C3—N2—C4	−177.1 (3)
O1—C6—C7—C12	159.4 (3)	C5—C3—N2—C4	3.3 (5)
C12—C7—C8—C9	−0.1 (4)	C2—C1—N2—C3	−0.9 (3)
C6—C7—C8—C9	−177.7 (3)	N4—C1—N2—C3	179.2 (3)
C7—C8—C9—C10	0.0 (5)	C2—C1—N2—C4	177.4 (3)
C8—C9—C10—C11	0.5 (5)	N4—C1—N2—C4	−2.5 (5)
C8—C9—C10—Br1	−178.8 (2)	C3—C5—N3—O1	179.2 (2)
C9—C10—C11—C12	−0.9 (4)	C2—C1—N4—O3	6.0 (5)
Br1—C10—C11—C12	178.4 (2)	N2—C1—N4—O3	−174.0 (3)
C10—C11—C12—C7	0.8 (4)	C2—C1—N4—O2	−174.7 (3)
C8—C7—C12—C11	−0.3 (4)	N2—C1—N4—O2	5.3 (4)
C6—C7—C12—C11	177.3 (3)	C5—N3—O1—C6	−171.8 (2)
N2—C3—N1—C2	−1.2 (3)	C7—C6—O1—N3	179.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4C···N3	0.98	2.24	2.997 (4)	133
C4—H4A···N1^i	0.98	2.62	3.499 (4)	149
C9—H9···N1^ii	0.95	2.77	3.681 (4)	160
C2—H2···O3^iii	0.95	2.44	3.282 (4)	148
C5—H5···O2^iv	0.95	2.64	3.341 (4)	131
C6—H6A···O2^v	0.99	2.63	3.254 (4)	121
C4—H4C···Br1^vi	0.98	2.85	3.491 (3)	124

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