Crystal structure and Hirshfeld surface analysis of (2E)-1-(4-bromo­phen­yl)-3-(2-methyl­phen­yl)prop-2-en-1-one

In the crystal of (2E)-1-(4-bromo­phen­yl)-3-(2-methyl­phen­yl)prop-2-en-1-one, the mol­ecules are linked into chains by weak C—H...O inter­actions along the b axis. Successive chains form a zigzag structure along the c axis, and these chains are connected to each other by face-to-face π–π stacking inter­actions along the a axis, forming layers parallel to the (001) plane. The crystal structure maintains its stability via van der Waals inter­actions between the layers.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.022
• wR factor = 0.052
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.530
           From the CIF: _refine_ls_abs_structure_Flack_su    0.020
PLAT141_ALERT_4_C s.u. on a - Axis Small or Missing ..............    0.00000 Ang.
PLAT907_ALERT_2_C Flack x > 0.5, Structure Needs to be Inverted? .       0.53 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT033_ALERT_4_G Flack x Value Deviates > 3.0 * sigma from Zero .      0.530 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         11 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   1 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2022); cell refinement: CrysAlis PRO (Rigaku OD, 2022); data reduction: CrysAlis PRO (Rigaku OD, 2022); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

(2E)-1-(4-Bromophenyl)-3-(2-methylphenyl)prop-2-en-1-one

Crystal data

C16H13BrO	Dx = 1.561 Mg m^−3
Mr = 301.17	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 12560 reflections
a = 3.942 Å	θ = 3.8–76.9°
b = 11.5915 (2) Å	µ = 4.23 mm^−1
c = 28.0387 (4) Å	T = 100 K
V = 1281.19 (3) Å^3	Needle, colourless
Z = 4	0.35 × 0.09 × 0.07 mm
F(000) = 608

Data collection

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	2627 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	Rint = 0.025
φ and ω scans	θmax = 77.1°, θmin = 3.2°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2022)	h = −4→4
Tmin = 0.251, Tmax = 1.000	k = −14→14
14537 measured reflections	l = −35→34
2657 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.022	w = 1/[σ^2(Fo^2) + (0.0121P)^2 + 1.3924P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.052	(Δ/σ)max = 0.001
S = 1.14	Δρmax = 0.51 e Å^−3
2657 reflections	Δρmin = −0.42 e Å^−3
165 parameters	Absolute structure: Refined as an inversion twin
0 restraints	Absolute structure parameter: 0.53 (2)

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.

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	Uiso*/Ueq
C1	0.6338 (7)	0.6732 (2)	0.28488 (10)	0.0156 (6)
C2	0.5186 (8)	0.5849 (3)	0.31975 (11)	0.0179 (6)
H2	0.576288	0.506108	0.315259	0.021*
C3	0.3333 (8)	0.6169 (3)	0.35751 (10)	0.0167 (6)
H3	0.272264	0.696111	0.359037	0.020*
C4	0.2138 (8)	0.5441 (3)	0.39673 (9)	0.0162 (5)
C5	0.0419 (8)	0.5941 (3)	0.43586 (11)	0.0199 (6)
C6	−0.0614 (9)	0.5231 (3)	0.47322 (11)	0.0243 (7)
H6	−0.174643	0.556148	0.499821	0.029*
C7	−0.0025 (9)	0.4050 (3)	0.47241 (12)	0.0260 (8)
H7	−0.075592	0.358302	0.498276	0.031*
C8	0.1629 (10)	0.3552 (3)	0.43386 (11)	0.0244 (7)
H8	0.202810	0.274348	0.433117	0.029*
C9	0.2691 (8)	0.4245 (3)	0.39655 (10)	0.0200 (6)
H9	0.382068	0.390249	0.370170	0.024*
C10	−0.0317 (9)	0.7216 (3)	0.43748 (12)	0.0225 (7)
H10A	−0.155611	0.739898	0.466828	0.034*
H10B	−0.169550	0.743225	0.409802	0.034*
H10C	0.182210	0.764687	0.436880	0.034*
C11	0.7811 (8)	0.6341 (2)	0.23829 (10)	0.0151 (5)
C12	0.7419 (7)	0.5219 (2)	0.22102 (9)	0.0170 (6)
H12	0.629276	0.465770	0.239962	0.020*
C13	0.8664 (8)	0.4916 (2)	0.17629 (11)	0.0180 (6)
H13	0.839832	0.415359	0.164401	0.022*
C14	1.0295 (8)	0.5750 (3)	0.14959 (10)	0.0170 (6)
C15	1.0768 (8)	0.6869 (3)	0.16597 (11)	0.0178 (6)
H15	1.193503	0.742210	0.147111	0.021*
C16	0.9500 (8)	0.7159 (3)	0.21041 (11)	0.0172 (6)
H16	0.978056	0.792262	0.222085	0.021*
Br1	1.19480 (8)	0.53645 (3)	0.08770 (2)	0.02188 (9)
O1	0.6109 (6)	0.77583 (19)	0.29371 (8)	0.0242 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0136 (15)	0.0168 (14)	0.0164 (13)	0.0005 (11)	−0.0014 (11)	0.0006 (11)
C2	0.0207 (16)	0.0164 (14)	0.0165 (14)	0.0013 (12)	0.0014 (12)	−0.0001 (11)
C3	0.0164 (13)	0.0177 (13)	0.0160 (13)	0.0015 (13)	−0.0028 (12)	−0.0018 (11)
C4	0.0129 (13)	0.0224 (13)	0.0134 (11)	−0.0004 (13)	−0.0030 (9)	0.0003 (11)
C5	0.0137 (14)	0.0316 (18)	0.0145 (14)	−0.0011 (13)	−0.0031 (12)	−0.0034 (13)
C6	0.0193 (14)	0.040 (2)	0.0142 (13)	−0.0042 (16)	−0.0013 (11)	−0.0015 (14)
C7	0.0249 (18)	0.038 (2)	0.0153 (15)	−0.0111 (15)	−0.0042 (13)	0.0066 (14)
C8	0.0264 (17)	0.0242 (16)	0.0226 (15)	−0.0024 (15)	−0.0079 (15)	0.0043 (12)
C9	0.0205 (17)	0.0229 (14)	0.0166 (13)	0.0004 (12)	−0.0016 (11)	0.0005 (10)
C10	0.0194 (16)	0.0280 (17)	0.0203 (16)	0.0003 (14)	0.0009 (13)	−0.0072 (13)
C11	0.0128 (13)	0.0171 (13)	0.0155 (13)	0.0022 (11)	−0.0008 (11)	0.0023 (10)
C12	0.0162 (15)	0.0178 (14)	0.0170 (12)	−0.0007 (12)	0.0021 (10)	0.0043 (11)
C13	0.0200 (16)	0.0151 (14)	0.0190 (14)	0.0005 (11)	0.0005 (12)	−0.0003 (10)
C14	0.0133 (14)	0.0253 (16)	0.0123 (13)	0.0024 (11)	0.0009 (11)	−0.0012 (11)
C15	0.0160 (14)	0.0194 (15)	0.0181 (14)	−0.0021 (12)	−0.0007 (11)	0.0042 (11)
C16	0.0172 (14)	0.0151 (14)	0.0194 (14)	−0.0023 (12)	−0.0019 (12)	0.0009 (11)
Br1	0.02033 (14)	0.03011 (16)	0.01522 (13)	−0.00038 (13)	0.00375 (12)	−0.00153 (13)
O1	0.0303 (14)	0.0171 (11)	0.0252 (11)	0.0010 (9)	0.0064 (10)	−0.0025 (9)

Geometric parameters (Å, º)

C1—O1	1.218 (4)	C8—H8	0.9500
C1—C2	1.487 (4)	C9—H9	0.9500
C1—C11	1.500 (4)	C10—H10A	0.9800
C2—C3	1.339 (4)	C10—H10B	0.9800
C2—H2	0.9500	C10—H10C	0.9800
C3—C4	1.464 (4)	C11—C12	1.396 (4)
C3—H3	0.9500	C11—C16	1.398 (4)
C4—C9	1.404 (4)	C12—C13	1.392 (4)
C4—C5	1.414 (4)	C12—H12	0.9500
C5—C6	1.393 (5)	C13—C14	1.381 (4)
C5—C10	1.507 (5)	C13—H13	0.9500
C6—C7	1.388 (5)	C14—C15	1.389 (4)
C6—H6	0.9500	C14—Br1	1.907 (3)
C7—C8	1.389 (5)	C15—C16	1.384 (4)
C7—H7	0.9500	C15—H15	0.9500
C8—C9	1.384 (4)	C16—H16	0.9500
O1—C1—C2	121.1 (3)	C4—C9—H9	119.2
O1—C1—C11	120.1 (3)	C5—C10—H10A	109.5
C2—C1—C11	118.9 (3)	C5—C10—H10B	109.5
C3—C2—C1	119.7 (3)	H10A—C10—H10B	109.5
C3—C2—H2	120.1	C5—C10—H10C	109.5
C1—C2—H2	120.1	H10A—C10—H10C	109.5
C2—C3—C4	127.6 (3)	H10B—C10—H10C	109.5
C2—C3—H3	116.2	C12—C11—C16	119.4 (3)
C4—C3—H3	116.2	C12—C11—C1	122.8 (3)
C9—C4—C5	118.8 (3)	C16—C11—C1	117.8 (3)
C9—C4—C3	121.1 (3)	C13—C12—C11	120.6 (3)
C5—C4—C3	120.1 (3)	C13—C12—H12	119.7
C6—C5—C4	118.8 (3)	C11—C12—H12	119.7
C6—C5—C10	120.0 (3)	C14—C13—C12	118.4 (3)
C4—C5—C10	121.2 (3)	C14—C13—H13	120.8
C7—C6—C5	121.4 (3)	C12—C13—H13	120.8
C7—C6—H6	119.3	C13—C14—C15	122.5 (3)
C5—C6—H6	119.3	C13—C14—Br1	119.2 (2)
C6—C7—C8	120.1 (3)	C15—C14—Br1	118.3 (2)
C6—C7—H7	119.9	C16—C15—C14	118.4 (3)
C8—C7—H7	119.9	C16—C15—H15	120.8
C9—C8—C7	119.3 (3)	C14—C15—H15	120.8
C9—C8—H8	120.4	C15—C16—C11	120.7 (3)
C7—C8—H8	120.4	C15—C16—H16	119.7
C8—C9—C4	121.6 (3)	C11—C16—H16	119.7
C8—C9—H9	119.2
O1—C1—C2—C3	12.0 (5)	C3—C4—C9—C8	178.7 (3)
C11—C1—C2—C3	−168.2 (3)	O1—C1—C11—C12	−164.3 (3)
C1—C2—C3—C4	−176.3 (3)	C2—C1—C11—C12	15.9 (4)
C2—C3—C4—C9	−4.4 (5)	O1—C1—C11—C16	12.6 (4)
C2—C3—C4—C5	175.1 (3)	C2—C1—C11—C16	−167.2 (3)
C9—C4—C5—C6	1.1 (5)	C16—C11—C12—C13	−0.6 (4)
C3—C4—C5—C6	−178.4 (3)	C1—C11—C12—C13	176.2 (3)
C9—C4—C5—C10	−178.6 (3)	C11—C12—C13—C14	0.1 (4)
C3—C4—C5—C10	1.9 (5)	C12—C13—C14—C15	0.8 (5)
C4—C5—C6—C7	−0.8 (5)	C12—C13—C14—Br1	−178.8 (2)
C10—C5—C6—C7	178.9 (3)	C13—C14—C15—C16	−1.1 (5)
C5—C6—C7—C8	0.1 (6)	Br1—C14—C15—C16	178.5 (2)
C6—C7—C8—C9	0.3 (5)	C14—C15—C16—C11	0.6 (5)
C7—C8—C9—C4	0.1 (5)	C12—C11—C16—C15	0.3 (5)
C5—C4—C9—C8	−0.7 (5)	C1—C11—C16—C15	−176.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.95	2.45	2.791 (4)	101
C12—H12···O1^i	0.95	2.58	3.200 (3)	124

Symmetry code: (i) −x+1, y−1/2, −z+1/2.