3-(2,6-Dichloro­phen­yl)-3-hydr­oxy-1-phenyl­propan-1-one

In the crystal structure of the title compound, C₁₅H₁₂Cl₂O₂, the chloro-substituted benzene rings are not parallel; the other rings are nearly parallel and the molecules stack in layers parallel to these rings. There are two molecules in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.049
• wR factor = 0.140
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4     ..  CL4     ..       2.87 Ang.

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

   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

3-(2,6-dichlorophenyl)-3-hydroxy-1-phenylpropan-1-one

Crystal data

C15H12Cl2O2	F(000) = 1216
Mr = 295.15	Dx = 1.451 Mg m^−3
Monoclinic, P21/c	Melting point: 374(375) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.2952 (14) Å	Cell parameters from 5943 reflections
b = 11.5678 (10) Å	θ = 2.3–27.9°
c = 14.6687 (12) Å	µ = 0.47 mm^−1
β = 102.230 (1)°	T = 273 K
V = 2702.3 (4) Å^3	Block, light-green
Z = 8	0.54 × 0.44 × 0.34 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4449 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 27.5°, θmin = 2.2°
φ and ω scans	h = −21→20
16721 measured reflections	k = −15→14
6171 independent reflections	l = −19→15

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.140	w = 1/[σ^2(Fo^2) + (0.0651P)^2 + 1.271P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
6171 reflections	Δρmax = 0.46 e Å^−3
437 parameters	Δρmin = −0.41 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0100 (10)

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
Cl3	0.25441 (4)	0.94861 (6)	0.41165 (5)	0.0611 (2)
Cl4	0.21452 (5)	0.78455 (7)	0.05536 (5)	0.0677 (2)
Cl2	0.93200 (5)	0.72977 (8)	0.57212 (5)	0.0727 (2)
Cl1	0.88389 (5)	0.50777 (7)	0.88542 (5)	0.0745 (2)
C1	0.90905 (14)	0.62182 (19)	0.73055 (15)	0.0433 (5)
C2	0.95900 (15)	0.6963 (2)	0.69037 (17)	0.0478 (5)
C6	0.93872 (15)	0.6005 (2)	0.82568 (16)	0.0495 (6)
C5	1.01105 (18)	0.6505 (3)	0.8767 (2)	0.0614 (7)
C3	1.03130 (16)	0.7467 (2)	0.7406 (2)	0.0583 (7)
C4	1.05665 (18)	0.7234 (3)	0.8335 (2)	0.0653 (8)
C7	0.60033 (13)	0.68364 (19)	0.59255 (15)	0.0420 (5)
C8	0.60720 (16)	0.8032 (2)	0.59746 (19)	0.0526 (6)
C12	0.52106 (16)	0.6345 (3)	0.57056 (18)	0.0556 (6)
C10	0.45781 (18)	0.8210 (3)	0.5587 (2)	0.0682 (8)
C11	0.45038 (17)	0.7027 (3)	0.5534 (2)	0.0666 (8)
C9	0.5358 (2)	0.8703 (3)	0.5804 (2)	0.0676 (8)
C17	0.23189 (13)	0.86710 (17)	0.23234 (15)	0.0389 (4)
C16	0.20872 (14)	0.94800 (18)	0.29301 (16)	0.0437 (5)
C18	0.19059 (13)	0.8782 (2)	0.13941 (16)	0.0447 (5)
C19	0.12999 (16)	0.9614 (3)	0.1085 (2)	0.0587 (7)
C20	0.10881 (18)	1.0370 (3)	0.1715 (2)	0.0655 (8)
C21	0.14789 (17)	1.0314 (2)	0.2636 (2)	0.0572 (6)
C25	0.53958 (14)	0.7414 (2)	0.32460 (15)	0.0440 (5)
C24	0.57187 (16)	0.8527 (2)	0.32941 (19)	0.0527 (6)
C26	0.59525 (17)	0.6493 (3)	0.3477 (2)	0.0596 (7)
C23	0.65711 (18)	0.8715 (3)	0.3575 (2)	0.0677 (8)
C27	0.68029 (18)	0.6690 (3)	0.3761 (2)	0.0723 (9)
C22	0.71102 (18)	0.7800 (3)	0.3815 (2)	0.0710 (8)
C30	0.44832 (14)	0.71587 (19)	0.29520 (16)	0.0438 (5)
C29	0.38532 (14)	0.8136 (2)	0.28530 (19)	0.0435 (5)
C28	0.29524 (14)	0.77119 (18)	0.26312 (17)	0.0424 (5)
C14	0.75970 (15)	0.6571 (2)	0.65023 (19)	0.0492 (6)
C13	0.67505 (14)	0.60741 (19)	0.60843 (16)	0.0450 (5)
C15	0.82778 (15)	0.5696 (2)	0.67793 (17)	0.0477 (5)
O1	0.42389 (11)	0.61682 (15)	0.27974 (15)	0.0662 (5)
O3	0.66778 (12)	0.50563 (15)	0.58650 (16)	0.0714 (6)
O2	0.27356 (13)	0.71289 (17)	0.34007 (16)	0.0643 (5)
O4	0.84486 (15)	0.5037 (2)	0.60308 (18)	0.0874 (7)
H4	0.8020	0.4703	0.5767	0.131*
H8	0.6596 (17)	0.840 (2)	0.6078 (18)	0.058 (7)*
H18	0.3950 (17)	0.856 (3)	0.343 (2)	0.063 (8)*
H13	0.108 (2)	0.962 (3)	0.049 (2)	0.073 (9)*
H19	0.3955 (16)	0.858 (2)	0.2358 (19)	0.059 (8)*
H1	1.0246 (19)	0.634 (3)	0.936 (2)	0.072 (9)*
H6	0.774 (2)	0.710 (3)	0.602 (2)	0.080 (10)*
H3	1.0634 (19)	0.792 (3)	0.706 (2)	0.072 (9)*
H7	0.7571 (18)	0.707 (3)	0.705 (2)	0.072 (9)*
H15	0.1331 (19)	1.079 (3)	0.312 (2)	0.072 (9)*
H2	1.104 (2)	0.753 (3)	0.866 (2)	0.072 (9)*
H24	0.5726 (19)	0.574 (3)	0.346 (2)	0.072 (9)*
H14	0.064 (2)	1.087 (3)	0.149 (2)	0.081 (10)*
H17	0.2899 (15)	0.715 (2)	0.2125 (18)	0.049 (7)*
H20	0.5366 (16)	0.910 (2)	0.3139 (17)	0.049 (7)*
H23	0.716 (2)	0.610 (3)	0.390 (2)	0.087 (10)*
H22	0.773 (2)	0.792 (3)	0.397 (2)	0.084 (10)*
H11	0.399 (2)	0.674 (3)	0.539 (2)	0.068 (9)*
H10	0.409 (2)	0.863 (3)	0.547 (2)	0.077 (9)*
H5	0.8178 (18)	0.492 (3)	0.717 (2)	0.074 (9)*
H12	0.5172 (19)	0.549 (3)	0.568 (2)	0.072 (9)*
H9	0.543 (2)	0.949 (3)	0.583 (2)	0.088 (11)*
H21	0.6781 (19)	0.948 (3)	0.361 (2)	0.073 (9)*
H16	0.308 (2)	0.667 (4)	0.350 (3)	0.105 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl3	0.0694 (4)	0.0571 (4)	0.0550 (4)	−0.0039 (3)	0.0089 (3)	−0.0089 (3)
Cl4	0.0680 (4)	0.0818 (5)	0.0509 (4)	0.0107 (4)	0.0068 (3)	−0.0097 (3)
Cl2	0.0712 (5)	0.0918 (6)	0.0569 (4)	−0.0006 (4)	0.0173 (3)	0.0207 (4)
Cl1	0.0817 (5)	0.0834 (5)	0.0625 (4)	0.0180 (4)	0.0244 (4)	0.0260 (4)
C1	0.0425 (11)	0.0414 (11)	0.0450 (12)	0.0111 (9)	0.0070 (9)	−0.0014 (9)
C2	0.0463 (12)	0.0475 (13)	0.0496 (13)	0.0094 (10)	0.0106 (10)	0.0019 (10)
C6	0.0508 (13)	0.0517 (13)	0.0459 (13)	0.0189 (11)	0.0102 (10)	0.0018 (10)
C5	0.0564 (16)	0.0742 (19)	0.0476 (15)	0.0241 (14)	−0.0023 (12)	−0.0064 (13)
C3	0.0445 (13)	0.0523 (14)	0.0780 (19)	0.0050 (11)	0.0125 (13)	−0.0034 (13)
C4	0.0461 (15)	0.0671 (18)	0.075 (2)	0.0103 (13)	−0.0048 (14)	−0.0176 (15)
C7	0.0409 (11)	0.0430 (12)	0.0405 (11)	−0.0027 (9)	0.0053 (9)	0.0021 (9)
C8	0.0469 (13)	0.0427 (13)	0.0661 (16)	−0.0011 (10)	0.0069 (11)	−0.0014 (11)
C12	0.0484 (14)	0.0598 (16)	0.0563 (15)	−0.0109 (12)	0.0055 (11)	−0.0012 (12)
C10	0.0503 (15)	0.091 (2)	0.0591 (17)	0.0223 (15)	0.0021 (12)	−0.0047 (15)
C11	0.0405 (14)	0.096 (2)	0.0604 (17)	−0.0057 (14)	0.0043 (12)	−0.0071 (15)
C9	0.0667 (18)	0.0530 (17)	0.078 (2)	0.0167 (14)	0.0041 (15)	−0.0046 (14)
C17	0.0349 (10)	0.0308 (10)	0.0493 (12)	−0.0024 (8)	0.0050 (9)	0.0022 (8)
C16	0.0442 (11)	0.0342 (11)	0.0518 (13)	−0.0020 (9)	0.0084 (10)	0.0018 (9)
C18	0.0378 (11)	0.0473 (12)	0.0488 (12)	−0.0010 (9)	0.0084 (9)	0.0053 (10)
C19	0.0464 (14)	0.0690 (17)	0.0579 (16)	0.0096 (12)	0.0049 (12)	0.0205 (14)
C20	0.0561 (15)	0.0552 (16)	0.086 (2)	0.0211 (13)	0.0161 (14)	0.0209 (15)
C21	0.0595 (15)	0.0392 (13)	0.0756 (18)	0.0104 (11)	0.0205 (14)	0.0030 (12)
C25	0.0444 (12)	0.0479 (13)	0.0418 (12)	0.0086 (9)	0.0138 (9)	0.0051 (9)
C24	0.0447 (13)	0.0525 (14)	0.0611 (15)	0.0055 (11)	0.0116 (11)	0.0016 (12)
C26	0.0550 (15)	0.0568 (16)	0.0697 (17)	0.0148 (12)	0.0190 (13)	0.0151 (13)
C23	0.0519 (15)	0.075 (2)	0.075 (2)	−0.0073 (14)	0.0122 (14)	−0.0014 (16)
C27	0.0507 (16)	0.090 (2)	0.079 (2)	0.0281 (16)	0.0183 (14)	0.0283 (17)
C22	0.0421 (14)	0.101 (3)	0.0696 (19)	0.0051 (15)	0.0111 (13)	0.0157 (17)
C30	0.0466 (12)	0.0378 (11)	0.0480 (12)	0.0050 (9)	0.0125 (10)	0.0024 (9)
C29	0.0400 (11)	0.0364 (11)	0.0537 (14)	0.0019 (9)	0.0091 (10)	0.0015 (10)
C28	0.0412 (11)	0.0325 (11)	0.0513 (13)	0.0025 (8)	0.0048 (9)	0.0008 (9)
C14	0.0433 (12)	0.0468 (13)	0.0560 (14)	0.0027 (10)	0.0068 (11)	−0.0069 (11)
C13	0.0489 (12)	0.0370 (11)	0.0470 (12)	−0.0028 (9)	0.0058 (10)	0.0056 (9)
C15	0.0476 (12)	0.0436 (12)	0.0495 (13)	0.0033 (10)	0.0049 (10)	−0.0007 (10)
O1	0.0571 (11)	0.0374 (9)	0.1043 (16)	0.0047 (8)	0.0174 (10)	−0.0032 (9)
O3	0.0656 (12)	0.0328 (9)	0.1045 (16)	−0.0008 (8)	−0.0074 (11)	0.0023 (9)
O2	0.0589 (11)	0.0468 (10)	0.0916 (15)	0.0102 (9)	0.0256 (10)	0.0279 (10)
O4	0.0803 (15)	0.0850 (16)	0.0959 (17)	0.0070 (12)	0.0159 (13)	−0.0357 (13)

Geometric parameters (Å, º)

Cl3—C16	1.742 (2)	C19—H13	0.87 (3)
Cl4—C18	1.746 (2)	C20—C21	1.367 (4)
Cl2—C2	1.740 (2)	C20—H14	0.93 (3)
Cl1—C6	1.746 (3)	C21—H15	0.97 (3)
C1—C2	1.399 (3)	C25—C24	1.387 (4)
C1—C6	1.399 (3)	C25—C26	1.394 (3)
C1—C15	1.511 (3)	C25—C30	1.488 (3)
C2—C3	1.379 (4)	C24—C23	1.380 (4)
C6—C5	1.381 (4)	C24—H20	0.88 (3)
C5—C4	1.365 (5)	C26—C27	1.379 (4)
C5—H1	0.87 (3)	C26—H24	0.95 (3)
C3—C4	1.365 (4)	C23—C22	1.373 (5)
C3—H3	0.96 (3)	C23—H21	0.94 (3)
C4—H2	0.88 (3)	C27—C22	1.374 (5)
C7—C12	1.385 (3)	C27—H23	0.89 (4)
C7—C8	1.388 (3)	C22—H22	1.00 (3)
C7—C13	1.481 (3)	C30—O1	1.218 (3)
C8—C9	1.377 (4)	C30—C29	1.513 (3)
C8—H8	0.93 (3)	C29—C28	1.516 (3)
C12—C11	1.375 (4)	C29—H18	0.97 (3)
C12—H12	0.99 (3)	C29—H19	0.93 (3)
C10—C9	1.367 (5)	C28—O2	1.422 (3)
C10—C11	1.374 (5)	C28—H17	0.97 (3)
C10—H10	0.92 (3)	C14—C15	1.493 (3)
C11—H11	0.89 (3)	C14—C13	1.500 (3)
C9—H9	0.92 (4)	C14—H6	1.00 (3)
C17—C18	1.392 (3)	C14—H7	1.01 (3)
C17—C16	1.397 (3)	C13—O3	1.220 (3)
C17—C28	1.517 (3)	C15—O4	1.412 (3)
C16—C21	1.385 (3)	C15—H5	1.10 (3)
C18—C19	1.384 (3)	O2—H16	0.77 (4)
C19—C20	1.369 (4)	O4—H4	0.8200
C2—C1—C6	114.8 (2)	C20—C21—H15	124.3 (18)
C2—C1—C15	123.8 (2)	C16—C21—H15	115.9 (18)
C6—C1—C15	121.3 (2)	C24—C25—C26	118.5 (2)
C3—C2—C1	122.9 (2)	C24—C25—C30	123.0 (2)
C3—C2—Cl2	116.4 (2)	C26—C25—C30	118.6 (2)
C1—C2—Cl2	120.68 (19)	C23—C24—C25	120.6 (3)
C5—C6—C1	122.8 (3)	C23—C24—H20	121.2 (17)
C5—C6—Cl1	117.0 (2)	C25—C24—H20	118.2 (17)
C1—C6—Cl1	120.22 (19)	C27—C26—C25	120.5 (3)
C4—C5—C6	119.6 (3)	C27—C26—H24	121.5 (19)
C4—C5—H1	123 (2)	C25—C26—H24	117.9 (19)
C6—C5—H1	117 (2)	C22—C23—C24	120.2 (3)
C4—C3—C2	119.6 (3)	C22—C23—H21	120.1 (19)
C4—C3—H3	123.7 (19)	C24—C23—H21	119.7 (19)
C2—C3—H3	116.5 (19)	C22—C27—C26	120.2 (3)
C5—C4—C3	120.4 (3)	C22—C27—H23	119 (2)
C5—C4—H2	120 (2)	C26—C27—H23	121 (2)
C3—C4—H2	120 (2)	C23—C22—C27	120.0 (3)
C12—C7—C8	118.8 (2)	C23—C22—H22	121 (2)
C12—C7—C13	119.1 (2)	C27—C22—H22	119 (2)
C8—C7—C13	122.0 (2)	O1—C30—C25	120.5 (2)
C9—C8—C7	119.8 (3)	O1—C30—C29	119.8 (2)
C9—C8—H8	118.9 (17)	C25—C30—C29	119.71 (19)
C7—C8—H8	121.2 (17)	C30—C29—C28	112.64 (19)
C11—C12—C7	120.7 (3)	C30—C29—H18	108.3 (17)
C11—C12—H12	121.5 (18)	C28—C29—H18	108.9 (16)
C7—C12—H12	117.8 (18)	C30—C29—H19	104.9 (17)
C9—C10—C11	119.7 (3)	C28—C29—H19	109.6 (16)
C9—C10—H10	123 (2)	H18—C29—H19	113 (2)
C11—C10—H10	117 (2)	O2—C28—C29	112.0 (2)
C10—C11—C12	120.1 (3)	O2—C28—C17	108.37 (18)
C10—C11—H11	117 (2)	C29—C28—C17	113.19 (18)
C12—C11—H11	123 (2)	O2—C28—H17	107.0 (15)
C10—C9—C8	121.0 (3)	C29—C28—H17	107.7 (15)
C10—C9—H9	122 (2)	C17—C28—H17	108.2 (15)
C8—C9—H9	117 (2)	C15—C14—C13	114.7 (2)
C18—C17—C16	115.0 (2)	C15—C14—H6	109.9 (19)
C18—C17—C28	121.1 (2)	C13—C14—H6	105.9 (19)
C16—C17—C28	124.0 (2)	C15—C14—H7	109.2 (17)
C21—C16—C17	122.7 (2)	C13—C14—H7	111.0 (17)
C21—C16—Cl3	115.78 (19)	H6—C14—H7	106 (3)
C17—C16—Cl3	121.53 (17)	O3—C13—C7	120.2 (2)
C19—C18—C17	123.2 (2)	O3—C13—C14	120.5 (2)
C19—C18—Cl4	116.8 (2)	C7—C13—C14	119.4 (2)
C17—C18—Cl4	120.01 (17)	O4—C15—C14	114.3 (2)
C20—C19—C18	119.2 (3)	O4—C15—C1	108.5 (2)
C20—C19—H13	124 (2)	C14—C15—C1	112.9 (2)
C18—C19—H13	117 (2)	O4—C15—H5	92.2 (16)
C21—C20—C19	120.3 (3)	C14—C15—H5	121.0 (16)
C21—C20—H14	123 (2)	C1—C15—H5	105.7 (16)
C19—C20—H14	117 (2)	C28—O2—H16	101 (3)
C20—C21—C16	119.6 (3)	C15—O4—H4	109.5
C6—C1—C2—C3	−1.0 (3)	C17—C16—C21—C20	−0.7 (4)
C15—C1—C2—C3	177.4 (2)	Cl3—C16—C21—C20	180.0 (2)
C6—C1—C2—Cl2	178.83 (16)	C26—C25—C24—C23	−0.7 (4)
C15—C1—C2—Cl2	−2.8 (3)	C30—C25—C24—C23	179.7 (2)
C2—C1—C6—C5	0.9 (3)	C24—C25—C26—C27	1.0 (4)
C15—C1—C6—C5	−177.4 (2)	C30—C25—C26—C27	−179.4 (3)
C2—C1—C6—Cl1	−179.19 (17)	C25—C24—C23—C22	−0.3 (4)
C15—C1—C6—Cl1	2.4 (3)	C25—C26—C27—C22	−0.3 (5)
C1—C6—C5—C4	−0.4 (4)	C24—C23—C22—C27	1.0 (5)
Cl1—C6—C5—C4	179.8 (2)	C26—C27—C22—C23	−0.7 (5)
C1—C2—C3—C4	0.4 (4)	C24—C25—C30—O1	169.9 (2)
Cl2—C2—C3—C4	−179.4 (2)	C26—C25—C30—O1	−9.6 (3)
C6—C5—C4—C3	−0.3 (4)	C24—C25—C30—C29	−10.7 (3)
C2—C3—C4—C5	0.2 (4)	C26—C25—C30—C29	169.8 (2)
C12—C7—C8—C9	−0.1 (4)	O1—C30—C29—C28	4.4 (3)
C13—C7—C8—C9	178.8 (2)	C25—C30—C29—C28	−175.0 (2)
C8—C7—C12—C11	0.3 (4)	C30—C29—C28—O2	69.7 (3)
C13—C7—C12—C11	−178.6 (2)	C30—C29—C28—C17	−167.4 (2)
C9—C10—C11—C12	0.4 (5)	C18—C17—C28—O2	−128.7 (2)
C7—C12—C11—C10	−0.5 (4)	C16—C17—C28—O2	49.6 (3)
C11—C10—C9—C8	−0.2 (5)	C18—C17—C28—C29	106.4 (2)
C7—C8—C9—C10	0.0 (5)	C16—C17—C28—C29	−75.3 (3)
C18—C17—C16—C21	1.4 (3)	C12—C7—C13—O3	12.9 (4)
C28—C17—C16—C21	−177.0 (2)	C8—C7—C13—O3	−166.0 (3)
C18—C17—C16—Cl3	−179.34 (16)	C12—C7—C13—C14	−168.1 (2)
C28—C17—C16—Cl3	2.3 (3)	C8—C7—C13—C14	13.0 (3)
C16—C17—C18—C19	−1.0 (3)	C15—C14—C13—O3	−10.9 (4)
C28—C17—C18—C19	177.4 (2)	C15—C14—C13—C7	170.1 (2)
C16—C17—C18—Cl4	178.90 (16)	C13—C14—C15—O4	62.6 (3)
C28—C17—C18—Cl4	−2.7 (3)	C13—C14—C15—C1	−172.7 (2)
C17—C18—C19—C20	0.0 (4)	C2—C1—C15—O4	59.5 (3)
Cl4—C18—C19—C20	−180.0 (2)	C6—C1—C15—O4	−122.3 (2)
C18—C19—C20—C21	0.8 (4)	C2—C1—C15—C14	−68.3 (3)
C19—C20—C21—C16	−0.5 (4)	C6—C1—C15—C14	110.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3	0.82	2.26	2.844 (3)	129
O2—H16···O1	0.77 (4)	2.41 (4)	2.990 (3)	134 (4)
O4—H4···Cl4^i	0.82	2.87	3.437 (2)	128
O2—H16···O3^ii	0.77 (4)	2.20 (4)	2.833 (3)	141 (4)

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