Crystal structure of 2-[(E)-2-(4-bromo­phen­yl)diazen-1-yl]-4,5-bis­(4-meth­oxy­phen­yl)-1H-imidazole: the first example of a structurally characterized tri­aryl­azo­imid­azole

The mol­ecule of the title compound adopts a trans configuration with respect to the azo double bond.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.052
• wR factor = 0.122
• Data-to-parameter ratio = 22.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.063 Report

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         41 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 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
   1 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

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Computing details

Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

2-[(E)-2-(4-Bromophenyl)diazen-1-yl]-4,5-bis(4-methoxyphenyl)-1H-imidazole

Crystal data

C23H19BrN4O2	F(000) = 944
Mr = 463.32	Dx = 1.533 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.7812 (9) Å	Cell parameters from 2288 reflections
b = 12.7877 (11) Å	θ = 2.6–25.4°
c = 15.4575 (13) Å	µ = 2.08 mm^−1
β = 109.635 (2)°	T = 120 K
V = 2007.2 (3) Å^3	Plate, orange
Z = 4	0.33 × 0.21 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer	3449 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.084
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 30.5°, θmin = 2.0°
Tmin = 0.597, Tmax = 0.746	h = −14→15
22147 measured reflections	k = −18→18
6069 independent reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: mixed
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0498P)^2] where P = (Fo^2 + 2Fc^2)/3
6069 reflections	(Δ/σ)max < 0.001
276 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.61 e Å^−3

Special details

Experimental. SADABS-2014/5 (Bruker, 2014/5) was used for absorption correction. wR2(int) was 0.0815 before and 0.0536 after correction. The Ratio of minimum to maximum transmission is 0.8000. The λ/2 correction factor is 0.00150.

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
Br1	0.27445 (4)	0.40711 (3)	−0.14822 (2)	0.04431 (14)
O1	−0.01642 (18)	0.55364 (14)	0.68807 (12)	0.0212 (4)
O2	0.84035 (18)	0.33604 (14)	0.90163 (12)	0.0249 (4)
N1	0.2914 (2)	0.39235 (17)	0.42224 (15)	0.0191 (5)
H1	0.222 (3)	0.410 (2)	0.387 (2)	0.023*
N2	0.5047 (2)	0.35277 (17)	0.47136 (14)	0.0194 (5)
N3	0.4041 (2)	0.36812 (17)	0.30966 (15)	0.0204 (5)
N4	0.2927 (2)	0.38470 (16)	0.24827 (15)	0.0215 (5)
C1	0.3985 (3)	0.36862 (19)	0.39831 (17)	0.0176 (5)
C2	0.4641 (3)	0.37005 (19)	0.54552 (17)	0.0162 (5)
C3	0.3314 (3)	0.39603 (19)	0.51634 (17)	0.0178 (5)
C4	0.2423 (3)	0.43346 (19)	0.56408 (17)	0.0163 (5)
C5	0.2757 (3)	0.5239 (2)	0.61663 (17)	0.0192 (6)
H5	0.3570	0.5577	0.6235	0.023*
C6	0.1921 (3)	0.56603 (19)	0.65933 (17)	0.0177 (6)
H6	0.2161	0.6281	0.6949	0.021*
C7	0.0742 (3)	0.51714 (19)	0.64976 (17)	0.0175 (5)
C8	0.0393 (3)	0.4255 (2)	0.59788 (18)	0.0203 (6)
H8	−0.0416	0.3915	0.5918	0.024*
C9	0.1230 (3)	0.38447 (19)	0.55551 (17)	0.0190 (6)
H9	0.0990	0.3223	0.5202	0.023*
C10	0.0165 (3)	0.6508 (2)	0.7369 (2)	0.0321 (7)
H10A	0.0296	0.7048	0.6958	0.048*
H10B	0.0978	0.6422	0.7895	0.048*
H10C	−0.0552	0.6717	0.7588	0.048*
C11	0.5584 (3)	0.36163 (19)	0.64007 (17)	0.0175 (5)
C12	0.5186 (3)	0.34390 (19)	0.71556 (18)	0.0195 (6)
H12	0.4273	0.3382	0.7065	0.023*
C13	0.6090 (3)	0.3342 (2)	0.80404 (18)	0.0201 (6)
H13	0.5800	0.3203	0.8545	0.024*
C14	0.7421 (3)	0.34526 (19)	0.81732 (17)	0.0199 (6)
C15	0.7843 (3)	0.3655 (2)	0.74336 (18)	0.0208 (6)
H15	0.8753	0.3754	0.7531	0.025*
C16	0.6935 (3)	0.3714 (2)	0.65562 (18)	0.0200 (6)
H16	0.7232	0.3822	0.6050	0.024*
C17	0.7997 (3)	0.3123 (2)	0.97884 (18)	0.0289 (7)
H17A	0.7433	0.2501	0.9652	0.043*
H17B	0.7506	0.3716	0.9911	0.043*
H17C	0.8775	0.2989	1.0329	0.043*
C18	0.2974 (3)	0.38963 (19)	0.15723 (18)	0.0198 (6)
C19	0.4131 (3)	0.3895 (2)	0.13582 (18)	0.0234 (6)
H19	0.4961	0.3872	0.1835	0.028*
C20	0.4069 (3)	0.3928 (2)	0.04512 (19)	0.0270 (7)
H20	0.4851	0.3907	0.0298	0.032*
C21	0.2842 (3)	0.3992 (2)	−0.02354 (18)	0.0272 (7)
C22	0.1682 (3)	0.4025 (2)	−0.0033 (2)	0.0294 (7)
H22	0.0853	0.4075	−0.0508	0.035*
C23	0.1765 (3)	0.3983 (2)	0.08831 (19)	0.0250 (6)
H23	0.0984	0.4014	0.1037	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0599 (3)	0.0551 (2)	0.01949 (15)	0.01172 (18)	0.01531 (15)	0.00843 (14)
O1	0.0173 (10)	0.0258 (10)	0.0236 (10)	−0.0033 (8)	0.0110 (8)	−0.0072 (8)
O2	0.0192 (11)	0.0302 (11)	0.0220 (10)	−0.0016 (8)	0.0025 (8)	0.0041 (8)
N1	0.0171 (12)	0.0223 (12)	0.0187 (11)	0.0021 (10)	0.0073 (10)	0.0012 (9)
N2	0.0197 (13)	0.0231 (12)	0.0192 (11)	0.0024 (9)	0.0116 (10)	0.0030 (9)
N3	0.0207 (13)	0.0200 (11)	0.0223 (11)	0.0010 (9)	0.0098 (10)	0.0001 (9)
N4	0.0229 (13)	0.0228 (12)	0.0212 (11)	−0.0008 (9)	0.0105 (10)	−0.0023 (9)
C1	0.0159 (14)	0.0201 (13)	0.0200 (13)	0.0009 (10)	0.0103 (11)	−0.0004 (10)
C2	0.0165 (14)	0.0168 (12)	0.0180 (12)	−0.0010 (10)	0.0096 (11)	0.0015 (9)
C3	0.0200 (14)	0.0182 (13)	0.0170 (12)	0.0008 (11)	0.0089 (11)	0.0011 (10)
C4	0.0156 (14)	0.0189 (13)	0.0157 (12)	0.0033 (10)	0.0068 (11)	0.0025 (9)
C5	0.0158 (14)	0.0244 (14)	0.0180 (12)	−0.0027 (11)	0.0062 (11)	0.0012 (10)
C6	0.0177 (14)	0.0189 (13)	0.0167 (12)	−0.0004 (10)	0.0062 (11)	−0.0008 (9)
C7	0.0159 (14)	0.0224 (14)	0.0162 (12)	0.0029 (11)	0.0080 (11)	0.0024 (10)
C8	0.0159 (14)	0.0224 (14)	0.0235 (13)	−0.0059 (10)	0.0080 (11)	−0.0009 (10)
C9	0.0214 (15)	0.0171 (14)	0.0204 (13)	0.0001 (10)	0.0095 (12)	−0.0023 (10)
C10	0.0271 (18)	0.0387 (18)	0.0361 (18)	−0.0066 (14)	0.0181 (15)	−0.0197 (14)
C11	0.0213 (15)	0.0138 (12)	0.0204 (13)	0.0017 (10)	0.0108 (11)	0.0014 (10)
C12	0.0167 (14)	0.0206 (14)	0.0228 (13)	0.0000 (11)	0.0087 (11)	0.0022 (10)
C13	0.0216 (15)	0.0205 (14)	0.0200 (13)	0.0005 (11)	0.0094 (12)	0.0015 (10)
C14	0.0197 (15)	0.0154 (13)	0.0210 (13)	−0.0009 (10)	0.0021 (11)	0.0008 (10)
C15	0.0176 (15)	0.0185 (13)	0.0289 (14)	0.0020 (11)	0.0112 (12)	0.0030 (11)
C16	0.0179 (15)	0.0199 (13)	0.0251 (14)	0.0019 (11)	0.0112 (12)	0.0025 (10)
C17	0.0272 (17)	0.0354 (17)	0.0201 (14)	−0.0006 (13)	0.0027 (13)	0.0011 (12)
C18	0.0239 (16)	0.0168 (13)	0.0215 (13)	−0.0027 (11)	0.0113 (12)	0.0003 (10)
C19	0.0246 (16)	0.0261 (15)	0.0205 (13)	0.0041 (12)	0.0087 (12)	0.0030 (11)
C20	0.0264 (17)	0.0315 (16)	0.0271 (15)	0.0039 (13)	0.0141 (13)	0.0044 (12)
C21	0.0401 (19)	0.0242 (15)	0.0184 (13)	0.0012 (13)	0.0113 (13)	0.0024 (11)
C22	0.0322 (18)	0.0274 (16)	0.0235 (14)	−0.0054 (13)	0.0028 (13)	−0.0007 (12)
C23	0.0203 (15)	0.0297 (16)	0.0245 (14)	−0.0048 (12)	0.0069 (12)	−0.0008 (12)

Geometric parameters (Å, º)

Br1—C21	1.897 (3)	C10—H10A	0.9800
O1—C7	1.382 (3)	C10—H10B	0.9800
O1—C10	1.435 (3)	C10—H10C	0.9800
O2—C14	1.381 (3)	C11—C12	1.390 (4)
O2—C17	1.435 (3)	C11—C16	1.400 (4)
N1—C1	1.360 (3)	C12—C13	1.393 (4)
N1—C3	1.372 (3)	C12—H12	0.9500
N1—H1	0.80 (3)	C13—C14	1.387 (4)
N2—C1	1.326 (3)	C13—H13	0.9500
N2—C2	1.375 (3)	C14—C15	1.389 (4)
N3—N4	1.274 (3)	C15—C16	1.382 (4)
N3—C1	1.392 (3)	C15—H15	0.9500
N4—C18	1.427 (3)	C16—H16	0.9500
C2—C3	1.388 (4)	C17—H17A	0.9800
C2—C11	1.477 (4)	C17—H17B	0.9800
C3—C4	1.474 (4)	C17—H17C	0.9800
C4—C5	1.390 (3)	C18—C23	1.383 (4)
C4—C9	1.397 (4)	C18—C19	1.393 (4)
C5—C6	1.392 (4)	C19—C20	1.382 (4)
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.379 (4)	C20—C21	1.392 (4)
C6—H6	0.9500	C20—H20	0.9500
C7—C8	1.399 (3)	C21—C22	1.388 (5)
C8—C9	1.384 (4)	C22—C23	1.389 (4)
C8—H8	0.9500	C22—H22	0.9500
C9—H9	0.9500	C23—H23	0.9500
C7—O1—C10	115.6 (2)	C12—C11—C2	122.6 (2)
C14—O2—C17	116.8 (2)	C16—C11—C2	119.6 (2)
C1—N1—C3	107.6 (2)	C11—C12—C13	121.8 (3)
C1—N1—H1	125 (2)	C11—C12—H12	119.1
C3—N1—H1	127 (2)	C13—C12—H12	119.1
C1—N2—C2	105.0 (2)	C14—C13—C12	119.0 (2)
N4—N3—C1	113.0 (2)	C14—C13—H13	120.5
N3—N4—C18	113.9 (2)	C12—C13—H13	120.5
N2—C1—N1	111.8 (2)	O2—C14—C13	123.9 (2)
N2—C1—N3	121.8 (2)	O2—C14—C15	115.7 (2)
N1—C1—N3	126.2 (2)	C13—C14—C15	120.4 (2)
N2—C2—C3	110.5 (2)	C16—C15—C14	119.9 (3)
N2—C2—C11	120.5 (2)	C16—C15—H15	120.1
C3—C2—C11	129.1 (2)	C14—C15—H15	120.1
N1—C3—C2	105.0 (2)	C15—C16—C11	121.1 (2)
N1—C3—C4	121.1 (2)	C15—C16—H16	119.4
C2—C3—C4	133.5 (2)	C11—C16—H16	119.4
C5—C4—C9	118.6 (2)	O2—C17—H17A	109.5
C5—C4—C3	118.6 (2)	O2—C17—H17B	109.5
C9—C4—C3	122.8 (2)	H17A—C17—H17B	109.5
C4—C5—C6	121.2 (3)	O2—C17—H17C	109.5
C4—C5—H5	119.4	H17A—C17—H17C	109.5
C6—C5—H5	119.4	H17B—C17—H17C	109.5
C7—C6—C5	119.6 (2)	C23—C18—C19	120.3 (2)
C7—C6—H6	120.2	C23—C18—N4	115.2 (2)
C5—C6—H6	120.2	C19—C18—N4	124.4 (2)
C6—C7—O1	124.0 (2)	C20—C19—C18	119.9 (3)
C6—C7—C8	120.1 (2)	C20—C19—H19	120.0
O1—C7—C8	115.9 (2)	C18—C19—H19	120.0
C9—C8—C7	119.8 (2)	C19—C20—C21	119.0 (3)
C9—C8—H8	120.1	C19—C20—H20	120.5
C7—C8—H8	120.1	C21—C20—H20	120.5
C8—C9—C4	120.8 (2)	C22—C21—C20	121.8 (3)
C8—C9—H9	119.6	C22—C21—Br1	118.8 (2)
C4—C9—H9	119.6	C20—C21—Br1	119.4 (2)
O1—C10—H10A	109.5	C21—C22—C23	118.3 (3)
O1—C10—H10B	109.5	C21—C22—H22	120.8
H10A—C10—H10B	109.5	C23—C22—H22	120.8
O1—C10—H10C	109.5	C18—C23—C22	120.6 (3)
H10A—C10—H10C	109.5	C18—C23—H23	119.7
H10B—C10—H10C	109.5	C22—C23—H23	119.7
C12—C11—C16	117.8 (2)
C1—N3—N4—C18	177.1 (2)	C3—C4—C9—C8	−176.7 (2)
C2—N2—C1—N1	−1.7 (3)	N2—C2—C11—C12	−158.2 (2)
C2—N2—C1—N3	173.7 (2)	C3—C2—C11—C12	22.9 (4)
C3—N1—C1—N2	2.4 (3)	N2—C2—C11—C16	21.6 (3)
C3—N1—C1—N3	−172.7 (2)	C3—C2—C11—C16	−157.2 (3)
N4—N3—C1—N2	180.0 (2)	C16—C11—C12—C13	−1.1 (4)
N4—N3—C1—N1	−5.3 (4)	C2—C11—C12—C13	178.8 (2)
C1—N2—C2—C3	0.4 (3)	C11—C12—C13—C14	1.7 (4)
C1—N2—C2—C11	−178.7 (2)	C17—O2—C14—C13	0.8 (4)
C1—N1—C3—C2	−2.0 (3)	C17—O2—C14—C15	−178.4 (2)
C1—N1—C3—C4	171.9 (2)	C12—C13—C14—O2	−179.2 (2)
N2—C2—C3—N1	1.0 (3)	C12—C13—C14—C15	−0.1 (4)
C11—C2—C3—N1	180.0 (2)	O2—C14—C15—C16	177.1 (2)
N2—C2—C3—C4	−171.7 (3)	C13—C14—C15—C16	−2.1 (4)
C11—C2—C3—C4	7.2 (5)	C14—C15—C16—C11	2.7 (4)
N1—C3—C4—C5	−115.9 (3)	C12—C11—C16—C15	−1.2 (4)
C2—C3—C4—C5	55.9 (4)	C2—C11—C16—C15	179.0 (2)
N1—C3—C4—C9	61.2 (3)	N3—N4—C18—C23	174.5 (2)
C2—C3—C4—C9	−127.0 (3)	N3—N4—C18—C19	−7.5 (4)
C9—C4—C5—C6	−0.6 (4)	C23—C18—C19—C20	−3.2 (4)
C3—C4—C5—C6	176.6 (2)	N4—C18—C19—C20	178.9 (2)
C4—C5—C6—C7	0.2 (4)	C18—C19—C20—C21	1.8 (4)
C5—C6—C7—O1	−178.9 (2)	C19—C20—C21—C22	0.1 (4)
C5—C6—C7—C8	0.4 (4)	C19—C20—C21—Br1	178.5 (2)
C10—O1—C7—C6	2.6 (4)	C20—C21—C22—C23	−0.6 (4)
C10—O1—C7—C8	−176.7 (2)	Br1—C21—C22—C23	−179.0 (2)
C6—C7—C8—C9	−0.6 (4)	C19—C18—C23—C22	2.8 (4)
O1—C7—C8—C9	178.7 (2)	N4—C18—C23—C22	−179.2 (2)
C7—C8—C9—C4	0.1 (4)	C21—C22—C23—C18	−0.8 (4)
C5—C4—C9—C8	0.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.80 (3)	2.17 (3)	2.963 (3)	169 (3)

Symmetry code: (i) −x, −y+1, −z+1.