N-(4-Bromo­benzyl­idene)-2,4-dimethyl­aniline

The mol­ecule of the title compound, C₁₅H₁₄BrN, is twisted along the C=N bond, the dihedral angle between the aromatic rings being 56.5 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.044
• wR factor = 0.137
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.94
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.18
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.937
            Tmax scaled      0.545 Tmin scaled      0.385
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           27.50
           From the CIF: _reflns_number_total               2708
           Count of symmetry unique reflns         1548
           Completeness (_total/calc)            174.94%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1160
           Fraction of Friedel pairs measured     0.749
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_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
   3 ALERT level G = General alerts; check

   1 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
   2 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, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

N-(4-Bromobenzylidene)-2,4-dimethylaniline

Crystal data

C15H14BrN	F(000) = 584
Mr = 288.18	Dx = 1.423 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2607 reflections
a = 7.554 (1) Å	θ = 2.6–25.4°
b = 15.323 (1) Å	µ = 3.03 mm^−1
c = 11.714 (1) Å	T = 293 K
β = 97.134 (1)°	Block, yellow
V = 1345.5 (2) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker APEX CCD area-detector diffractometer	2708 independent reflections
Radiation source: fine-focus sealed tube	2328 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.411, Tmax = 0.582	k = −19→19
5715 measured reflections	l = −15→12

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)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.137	w = 1/[σ^2(Fo^2) + (0.0814P)^2 + 1.3037P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2708 reflections	Δρmax = 0.61 e Å^−3
157 parameters	Δρmin = −0.28 e Å^−3
2 restraints	Absolute structure: Flack (1983), 1169 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (2)

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

	x	y	z	Uiso*/Ueq
Br1	0.50000 (8)	1.12488 (3)	0.50000 (7)	0.0723 (2)
N1	0.4834 (6)	0.7111 (3)	0.2663 (4)	0.047 (1)
C1	0.5113 (6)	1.0054 (3)	0.4594 (5)	0.049 (1)
C2	0.5984 (6)	0.9470 (3)	0.5363 (4)	0.049 (1)
C3	0.6063 (7)	0.8605 (3)	0.5048 (4)	0.047 (1)
C4	0.5297 (6)	0.8330 (3)	0.3967 (4)	0.041 (1)
C5	0.4440 (7)	0.8932 (3)	0.3201 (5)	0.048 (1)
C6	0.4336 (7)	0.9800 (3)	0.3506 (5)	0.052 (1)
C7	0.5403 (6)	0.7399 (3)	0.3658 (4)	0.045 (1)
C8	0.4870 (6)	0.6196 (3)	0.2501 (4)	0.038 (1)
C9	0.4161 (7)	0.5625 (3)	0.3262 (4)	0.050 (1)
C10	0.4119 (7)	0.4740 (3)	0.3078 (5)	0.052 (1)
C11	0.4821 (7)	0.4377 (3)	0.2145 (5)	0.047 (1)
C12	0.5523 (6)	0.4947 (3)	0.1392 (5)	0.047 (1)
C13	0.5558 (6)	0.5846 (3)	0.1551 (4)	0.041 (1)
C14	0.4759 (9)	0.3409 (4)	0.1941 (6)	0.071 (2)
C15	0.6321 (9)	0.6436 (4)	0.0698 (6)	0.060 (1)
H2	0.6510	0.9656	0.6082	0.059*
H3	0.6632	0.8202	0.5563	0.056*
H5	0.3932	0.8749	0.2476	0.058*
H6	0.3761	1.0205	0.2996	0.063*
H7	0.5906	0.7008	0.4214	0.054*
H9	0.3710	0.5851	0.3904	0.059*
H10	0.3613	0.4378	0.3586	0.062*
H12	0.5988	0.4717	0.0757	0.056*
H14a	0.5003	0.3289	0.1172	0.106*
H14b	0.3596	0.3192	0.2041	0.106*
H14c	0.5639	0.3128	0.2480	0.106*
H15a	0.6794	0.6088	0.0126	0.091*
H15b	0.7256	0.6787	0.1094	0.091*
H15c	0.5396	0.6808	0.0333	0.091*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0869 (4)	0.0440 (3)	0.0857 (4)	0.0043 (3)	0.0092 (3)	−0.0209 (3)
N1	0.053 (2)	0.042 (2)	0.045 (2)	−0.001 (2)	0.005 (2)	−0.005 (2)
C1	0.046 (2)	0.039 (2)	0.063 (3)	−0.0010 (18)	0.010 (2)	−0.014 (2)
C2	0.052 (3)	0.053 (3)	0.042 (3)	−0.007 (2)	0.001 (2)	−0.015 (2)
C3	0.053 (3)	0.044 (2)	0.044 (3)	−0.002 (2)	0.005 (2)	0.004 (2)
C4	0.043 (2)	0.041 (2)	0.039 (2)	−0.005 (2)	0.010 (2)	−0.003 (2)
C5	0.052 (2)	0.048 (3)	0.044 (3)	0.004 (2)	0.003 (2)	−0.008 (2)
C6	0.058 (3)	0.044 (3)	0.053 (3)	0.005 (2)	0.000 (2)	−0.005 (2)
C7	0.042 (2)	0.045 (2)	0.047 (3)	0.000 (2)	0.005 (2)	−0.002 (2)
C8	0.042 (2)	0.041 (2)	0.032 (2)	−0.006 (2)	0.001 (2)	−0.002 (2)
C9	0.062 (3)	0.053 (3)	0.034 (2)	−0.007 (2)	0.012 (2)	−0.001 (2)
C10	0.058 (3)	0.050 (3)	0.047 (3)	−0.013 (2)	0.006 (2)	0.008 (2)
C11	0.052 (2)	0.039 (2)	0.047 (3)	−0.008 (2)	−0.001 (2)	0.002 (2)
C12	0.049 (2)	0.044 (3)	0.046 (3)	−0.001 (2)	0.001 (2)	−0.006 (2)
C13	0.048 (2)	0.040 (2)	0.036 (2)	−0.006 (2)	0.004 (2)	−0.001 (2)
C14	0.084 (4)	0.043 (3)	0.082 (5)	−0.009 (3)	−0.005 (4)	−0.003 (3)
C15	0.077 (3)	0.049 (3)	0.060 (4)	−0.009 (2)	0.029 (3)	−0.003 (2)

Geometric parameters (Å, º)

Br1—C1	1.896 (5)	C12—C13	1.390 (7)
N1—C7	1.270 (7)	C13—C15	1.514 (7)
N1—C8	1.416 (6)	C2—H2	0.93
C1—C2	1.378 (8)	C3—H3	0.93
C1—C6	1.391 (7)	C5—H5	0.93
C2—C3	1.380 (7)	C6—H6	0.93
C3—C4	1.390 (7)	C7—H7	0.93
C4—C5	1.391 (7)	C9—H9	0.93
C4—C7	1.476 (6)	C10—H10	0.93
C5—C6	1.383 (7)	C12—H12	0.93
C8—C13	1.392 (7)	C14—H14a	0.96
C8—C9	1.402 (7)	C14—H14b	0.96
C9—C10	1.373 (8)	C14—H14c	0.96
C10—C11	1.389 (8)	C15—H15a	0.96
C11—C12	1.392 (8)	C15—H15b	0.96
C11—C14	1.502 (8)	C15—H15c	0.96
C7—N1—C8	117.2 (4)	C2—C3—H3	119.7
C2—C1—C6	122.0 (4)	C4—C3—H3	119.7
C2—C1—Br1	119.7 (4)	C6—C5—H5	119.7
C6—C1—Br1	118.2 (4)	C4—C5—H5	119.7
C1—C2—C3	118.8 (4)	C5—C6—H6	120.8
C2—C3—C4	120.5 (5)	C1—C6—H6	120.8
C3—C4—C5	119.7 (4)	N1—C7—H7	118.7
C3—C4—C7	119.2 (4)	C4—C7—H7	118.7
C5—C4—C7	121.2 (4)	C10—C9—H9	119.3
C6—C5—C4	120.6 (5)	C8—C9—H9	119.3
C5—C6—C1	118.4 (5)	C9—C10—H10	119.5
N1—C7—C4	122.6 (5)	C11—C10—H10	119.5
C13—C8—C9	118.5 (4)	C13—C12—H12	118.7
C13—C8—N1	120.3 (4)	C11—C12—H12	118.7
C9—C8—N1	121.1 (4)	C11—C14—H14a	109.5
C10—C9—C8	121.3 (5)	C11—C14—H14b	109.5
C9—C10—C11	121.0 (5)	H14a—C14—H14b	109.5
C10—C11—C12	117.4 (5)	C11—C14—H14c	109.5
C10—C11—C14	120.9 (5)	H14a—C14—H14c	109.5
C12—C11—C14	121.7 (5)	H14b—C14—H14c	109.5
C13—C12—C11	122.6 (5)	C13—C15—H15a	109.5
C12—C13—C8	119.1 (4)	C13—C15—H15b	109.5
C12—C13—C15	120.4 (5)	H15a—C15—H15b	109.5
C8—C13—C15	120.5 (4)	C13—C15—H15c	109.5
C1—C2—H2	120.6	H15a—C15—H15c	109.5
C3—C2—H2	120.6	H15b—C15—H15c	109.5
C6—C1—C2—C3	−1.0 (8)	C7—N1—C8—C9	49.8 (7)
Br1—C1—C2—C3	−179.5 (4)	C13—C8—C9—C10	−0.7 (8)
C1—C2—C3—C4	0.9 (7)	N1—C8—C9—C10	177.0 (5)
C2—C3—C4—C5	−0.3 (7)	C8—C9—C10—C11	1.6 (8)
C2—C3—C4—C7	−179.9 (4)	C9—C10—C11—C12	−1.6 (7)
C3—C4—C5—C6	−0.3 (7)	C9—C10—C11—C14	−179.5 (5)
C7—C4—C5—C6	179.4 (5)	C10—C11—C12—C13	0.7 (7)
C4—C5—C6—C1	0.2 (8)	C14—C11—C12—C13	178.6 (5)
C2—C1—C6—C5	0.5 (8)	C11—C12—C13—C8	0.2 (7)
Br1—C1—C6—C5	179.0 (4)	C11—C12—C13—C15	−179.4 (5)
C8—N1—C7—C4	−174.7 (4)	C9—C8—C13—C12	−0.2 (7)
C3—C4—C7—N1	−175.5 (4)	N1—C8—C13—C12	−177.9 (4)
C5—C4—C7—N1	4.9 (7)	C9—C8—C13—C15	179.4 (5)
C7—N1—C8—C13	−132.5 (5)	N1—C8—C13—C15	1.7 (7)