N-[4-Cyano-3-(trifluoro­meth­yl)phen­yl]-3-(4-fluoro­phenyl­sulfon­yl)-2-hydr­oxy-2-methyl­propionamide

The structure of the title compound, C₁₈H₁₄F₄N₂O₂S, consists of mol­ecules that pack in a linear hydrogen-bonded chain along the c axis. This hydrogen-bonding arrangement involves the hydr­oxy group and one of the sulfonyl O atoms.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.098
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C8     -   C11     ..       5.01 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C8     -   C11    ...       1.45 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenylsulfonyl)- 2-hydroxy-2-methylpropionamide

Crystal data

C18H14F4N2O4S	F(000) = 880.00
Mr = 430.37	Dx = 1.554 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 14876 reflections
a = 14.882 (5) Å	θ = 3.0–27.5°
b = 12.213 (3) Å	µ = 0.24 mm^−1
c = 10.461 (3) Å	T = 296 K
β = 104.680 (13)°	Block, colourless
V = 1839.3 (9) Å^3	0.29 × 0.25 × 0.17 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2973 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.027
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −19→19
Tmin = 0.881, Tmax = 0.959	k = −15→15
17686 measured reflections	l = −13→11
4206 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[0.0006Fo^2 + 1.16σ(Fo^2)]/(4Fo^2)
wR(F^2) = 0.098	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.29 e Å^−3
4206 reflections	Δρmin = −0.39 e Å^−3
262 parameters

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
S1	0.34160 (3)	0.14708 (3)	0.80523 (4)	0.03962 (11)
F1	0.31765 (13)	0.69861 (11)	0.5144 (2)	0.1255 (7)
F2	0.30524 (11)	0.79072 (12)	0.68145 (16)	0.0936 (5)
F3	0.20991 (12)	0.81569 (10)	0.49787 (14)	0.0887 (4)
F4	0.65223 (11)	0.02895 (12)	0.58995 (18)	0.0999 (5)
O21	0.25122 (10)	0.18239 (10)	0.51043 (12)	0.0539 (3)
O22	0.10729 (12)	0.25848 (10)	0.71760 (16)	0.0699 (4)
O23	0.33168 (9)	0.26421 (9)	0.79782 (12)	0.0475 (3)
O24	0.35571 (10)	0.09517 (11)	0.93268 (11)	0.0555 (3)
N31	0.17082 (11)	0.35417 (10)	0.57536 (13)	0.0440 (4)
N32	0.10399 (12)	0.87647 (12)	0.74293 (19)	0.0655 (5)
C1	0.23860 (12)	0.08755 (12)	0.70465 (16)	0.0419 (4)
C2	0.18791 (12)	0.15556 (12)	0.58638 (16)	0.0421 (4)
C3	0.10517 (16)	0.09143 (17)	0.5067 (2)	0.0654 (6)
C4	0.15144 (12)	0.26156 (12)	0.63461 (17)	0.0444 (4)
C5	0.15184 (12)	0.46206 (12)	0.60581 (14)	0.0396 (4)
C6	0.07939 (12)	0.48993 (13)	0.65975 (17)	0.0467 (5)
C7	0.06677 (12)	0.59808 (13)	0.69100 (18)	0.0474 (5)
C8	0.12512 (12)	0.67921 (12)	0.66713 (16)	0.0432 (4)
C9	0.19556 (12)	0.65150 (12)	0.60718 (17)	0.0435 (4)
C10	0.20865 (12)	0.54404 (12)	0.57679 (17)	0.0433 (4)
C11	0.11321 (13)	0.79007 (14)	0.7084 (2)	0.0495 (5)
C12	0.25753 (17)	0.73792 (16)	0.5756 (2)	0.0657 (7)
C13	0.43448 (12)	0.11046 (13)	0.73879 (16)	0.0425 (4)
C14	0.48534 (14)	0.01695 (16)	0.7837 (2)	0.0574 (5)
C15	0.55891 (17)	−0.01021 (18)	0.7323 (2)	0.0704 (7)
C16	0.57945 (16)	0.05572 (19)	0.6399 (2)	0.0653 (6)
C17	0.53069 (14)	0.14876 (18)	0.5938 (2)	0.0635 (6)
C18	0.45702 (13)	0.17684 (14)	0.64421 (19)	0.0524 (5)
H6	0.0393	0.4359	0.6750	0.058*
H7	0.0185	0.6165	0.7286	0.059*
H10	0.2558	0.5259	0.5368	0.054*
H11	0.1961	0.0749	0.7597	0.052*
H12	0.2552	0.0181	0.6720	0.052*
H14	0.4693	−0.0264	0.8476	0.070*
H15	0.5944	−0.0725	0.7602	0.086*
H17	0.5472	0.1915	0.5298	0.080*
H18	0.4221	0.2393	0.6151	0.065*
H31	0.0770	0.1308	0.4273	0.075*
H32	0.0607	0.0822	0.5582	0.075*
H33	0.1253	0.0209	0.4844	0.075*
H211	0.2241	0.1666	0.4244	0.069*
H311	0.2088	0.3469	0.5289	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0468 (2)	0.0365 (2)	0.0393 (2)	−0.00418 (18)	0.01773 (18)	−0.00016 (17)
F1	0.1383 (15)	0.0606 (8)	0.232 (2)	−0.0169 (8)	0.1466 (16)	−0.0080 (10)
F2	0.0757 (10)	0.0776 (8)	0.1223 (12)	−0.0301 (7)	0.0158 (9)	−0.0040 (8)
F3	0.1166 (12)	0.0561 (7)	0.1001 (9)	−0.0068 (7)	0.0398 (9)	0.0290 (7)
F4	0.0755 (10)	0.1045 (11)	0.1411 (13)	0.0075 (8)	0.0667 (9)	−0.0202 (9)
O21	0.0712 (9)	0.0523 (7)	0.0472 (6)	0.0076 (6)	0.0318 (6)	0.0051 (5)
O22	0.0935 (12)	0.0459 (7)	0.0936 (10)	0.0101 (7)	0.0669 (9)	0.0134 (7)
O23	0.0569 (8)	0.0358 (5)	0.0549 (7)	−0.0069 (5)	0.0237 (6)	−0.0078 (5)
O24	0.0654 (9)	0.0625 (7)	0.0414 (6)	−0.0029 (6)	0.0187 (6)	0.0097 (5)
N31	0.0559 (9)	0.0360 (6)	0.0473 (7)	0.0047 (6)	0.0262 (6)	0.0043 (5)
N32	0.0626 (11)	0.0449 (9)	0.0948 (13)	0.0037 (8)	0.0308 (10)	−0.0072 (8)
C1	0.0470 (10)	0.0328 (7)	0.0486 (9)	−0.0047 (7)	0.0170 (7)	0.0010 (6)
C2	0.0520 (10)	0.0348 (7)	0.0428 (8)	−0.0012 (7)	0.0179 (7)	0.0005 (6)
C3	0.0708 (15)	0.0572 (11)	0.0595 (11)	−0.0072 (10)	0.0001 (10)	−0.0027 (9)
C4	0.0500 (11)	0.0377 (8)	0.0496 (9)	0.0019 (7)	0.0202 (8)	0.0050 (7)
C5	0.0451 (10)	0.0359 (7)	0.0396 (8)	0.0049 (7)	0.0138 (7)	0.0051 (6)
C6	0.0471 (11)	0.0403 (8)	0.0573 (10)	−0.0004 (7)	0.0217 (8)	0.0073 (7)
C7	0.0450 (11)	0.0459 (9)	0.0569 (10)	0.0069 (8)	0.0234 (8)	0.0036 (8)
C8	0.0462 (10)	0.0370 (8)	0.0479 (9)	0.0076 (7)	0.0148 (7)	0.0035 (6)
C9	0.0456 (10)	0.0380 (8)	0.0499 (9)	0.0017 (7)	0.0174 (7)	0.0061 (7)
C10	0.0465 (10)	0.0405 (8)	0.0486 (9)	0.0045 (7)	0.0227 (8)	0.0051 (7)
C11	0.0453 (11)	0.0432 (9)	0.0627 (11)	0.0045 (7)	0.0186 (9)	0.0023 (8)
C12	0.0701 (16)	0.0437 (10)	0.0958 (16)	−0.0053 (10)	0.0444 (13)	−0.0003 (11)
C13	0.0429 (10)	0.0420 (8)	0.0443 (8)	−0.0031 (7)	0.0144 (7)	−0.0015 (7)
C14	0.0605 (13)	0.0485 (10)	0.0660 (11)	0.0071 (9)	0.0213 (10)	0.0074 (9)
C15	0.0635 (14)	0.0552 (11)	0.0959 (16)	0.0158 (10)	0.0267 (12)	−0.0008 (11)
C16	0.0492 (13)	0.0713 (13)	0.0830 (14)	−0.0011 (10)	0.0311 (11)	−0.0198 (11)
C17	0.0556 (13)	0.0723 (13)	0.0719 (12)	−0.0065 (11)	0.0336 (10)	0.0025 (10)
C18	0.0527 (11)	0.0508 (10)	0.0603 (11)	0.0006 (8)	0.0262 (9)	0.0075 (8)

Geometric parameters (Å, º)

S1—O23	1.4382 (11)	C9—C10	1.376 (2)
S1—O24	1.4428 (12)	C9—C12	1.493 (3)
S1—C1	1.7798 (16)	C13—C14	1.385 (2)
S1—C13	1.7551 (19)	C13—C18	1.385 (2)
F1—C12	1.316 (3)	C14—C15	1.377 (3)
F2—C12	1.322 (2)	C15—C16	1.351 (3)
F3—C12	1.331 (2)	C16—C17	1.368 (3)
F4—C16	1.356 (3)	C17—C18	1.375 (3)
O21—C2	1.416 (2)	O21—H211	0.909
O22—C4	1.215 (2)	N31—H311	0.838
N31—C4	1.355 (2)	C1—H11	0.970
N31—C5	1.401 (2)	C1—H12	0.970
N32—C11	1.135 (2)	C3—H31	0.960
C1—C2	1.522 (2)	C3—H32	0.960
C2—C3	1.518 (2)	C3—H33	0.960
C2—C4	1.538 (2)	C6—H6	0.930
C5—C6	1.380 (2)	C7—H7	0.930
C5—C10	1.393 (2)	C10—H10	0.930
C6—C7	1.385 (2)	C14—H14	0.930
C7—C8	1.381 (2)	C15—H15	0.930
C8—C9	1.393 (2)	C17—H17	0.930
C8—C11	1.446 (2)	C18—H18	0.930
S1···O21^i	3.4955 (14)	C6···H31^i	3.171
F1···F2^ii	3.443 (2)	C6···H33^i	3.293
F1···F4^iii	3.565 (2)	C6···H211^i	3.596
F1···C17^iii	3.338 (3)	C7···H33^i	3.307
F2···F1^iv	3.443 (2)	C10···H11^viii	3.582
F2···C17^v	3.404 (2)	C10···H15^v	3.316
F3···F4^iii	3.100 (2)	C11···H6^xi	3.349
F3···C7^ii	3.534 (2)	C11···H12^xii	3.574
F3···C8^ii	3.370 (2)	C11···H31^xiii	2.988
F3···C11^ii	3.271 (2)	C12···H12^xii	3.570
F4···F1^iii	3.565 (2)	C12···H17^iii	3.467
F4···F3^iii	3.100 (2)	C15···H10^vii	3.203
F4···O21^vi	3.255 (2)	C15···H17^vi	3.566
F4···O23^vii	3.4275 (19)	C15···H18^vii	3.429
F4···C10^vii	3.580 (2)	C18···H15^v	3.368
F4···C18^vi	3.598 (2)	H6···N32^ix	2.596
O21···S1^viii	3.4955 (14)	H6···C3^i	3.376
O21···F4^vi	3.255 (2)	H6···C11^ix	3.349
O21···O22^viii	3.3418 (18)	H6···H31^i	2.682
O21···O23^viii	2.856 (2)	H6···H33^i	3.209
O21···O24^viii	3.3318 (19)	H6···H211^i	3.507
O22···O21^i	3.3418 (18)	H7···F3^iv	3.560
O22···N32^ix	3.576 (2)	H7···O22^xi	2.713
O22···C3^i	3.544 (2)	H7···N32^ix	3.504
O22···C7^ix	3.566 (2)	H7···H11^xi	3.266
O22···C11^ix	3.578 (2)	H7···H32^xi	2.806
O23···F4^v	3.4275 (19)	H7···H33^i	3.218
O23···O21^i	2.856 (2)	H10···O24^viii	2.531
O23···C15^v	3.256 (2)	H10···N32^ii	3.530
O24···O21^i	3.3318 (19)	H10···C15^v	3.203
O24···N31^i	3.502 (2)	H10···H11^viii	3.067
O24···C10^i	3.410 (2)	H10···H15^v	2.920
O24···C14^x	3.566 (2)	H11···N31^i	3.525
O24···C15^x	3.566 (2)	H11···N32^xiv	2.768
N31···O24^viii	3.502 (2)	H11···C10^i	3.582
N32···O22^xi	3.576 (2)	H11···H7^ix	3.266
N32···C1^xii	3.350 (2)	H11···H10^i	3.067
N32···C3^xiii	3.542 (2)	H11···H211^i	3.570
N32···C6^xi	3.437 (2)	H11···H311^i	2.934
N32···C10^iv	3.579 (2)	H12···F2^xiv	2.870
C1···N32^xiv	3.350 (2)	H12···F3^xiv	3.043
C3···O22^viii	3.544 (2)	H12···F4^vi	3.413
C3···N32^xiii	3.542 (2)	H12···N32^xiv	3.075
C6···N32^ix	3.437 (2)	H12···C11^xiv	3.574
C6···C6^xiii	3.579 (2)	H12···C12^xiv	3.570
C7···F3^iv	3.534 (2)	H14···F2^xiv	3.438
C7···O22^xi	3.566 (2)	H14···O24^x	3.121
C8···F3^iv	3.370 (2)	H14···H14^x	3.153
C10···F4^v	3.580 (2)	H14···H18^vii	3.261
C10···O24^viii	3.410 (2)	H15···O23^vii	2.428
C10···N32^ii	3.579 (2)	H15···O24^x	3.121
C10···C15^v	3.591 (2)	H15···N31^vii	3.595
C11···F3^iv	3.271 (2)	H15···C10^vii	3.316
C11···O22^xi	3.578 (2)	H15···C18^vii	3.368
C14···O24^x	3.566 (2)	H15···H10^vii	2.920
C15···O23^vii	3.256 (2)	H15···H17^vi	3.538
C15···O24^x	3.566 (2)	H15···H18^vii	2.684
C15···C10^vii	3.591 (2)	H15···H311^vii	3.338
C16···C16^vi	3.535 (3)	H17···F1^iii	2.555
C16···C17^vi	3.587 (3)	H17···F2^vii	3.472
C17···F1^iii	3.338 (3)	H17···F2^iii	3.494
C17···F2^vii	3.404 (2)	H17···O23^viii	3.539
C17···C16^vi	3.587 (3)	H17···C12^iii	3.467
C18···F4^vi	3.598 (2)	H17···C15^vi	3.566
S1···H18^i	3.449	H17···H15^vi	3.538
S1···H211^i	3.301	H18···S1^viii	3.449
S1···H311^i	3.425	H18···O23^viii	3.250
F1···H17^iii	2.555	H18···O24^viii	2.784
F2···H12^xii	2.870	H18···C15^v	3.429
F2···H14^xii	3.438	H18···H14^v	3.261
F2···H17^v	3.472	H18···H15^v	2.684
F2···H17^iii	3.494	H31···O22^viii	2.709
F3···H7^ii	3.560	H31···N32^xiii	2.829
F3···H12^xii	3.043	H31···C6^viii	3.171
F3···H33^xii	2.792	H31···C11^xiii	2.988
F4···H12^vi	3.413	H31···H6^viii	2.682
F4···H211^vi	3.042	H31···H32^xv	3.339
O22···H7^ix	2.713	H32···N32^xiv	3.135
O22···H31^i	2.709	H32···N32^xiii	3.503
O22···H211^i	2.575	H32···C3^xv	3.193
O22···H311^i	3.471	H32···H7^ix	2.806
O23···H15^v	2.428	H32···H31^xv	3.339
O23···H17^i	3.539	H32···H32^xv	2.767
O23···H18^i	3.250	H32···H33^xv	2.970
O23···H211^i	2.471	H33···F3^xiv	2.792
O24···H10^i	2.531	H33···N32^xiv	3.311
O24···H14^x	3.121	H33···C6^viii	3.293
O24···H15^x	3.121	H33···C7^viii	3.307
O24···H18^i	2.784	H33···H6^viii	3.209
O24···H211^i	3.497	H33···H7^viii	3.218
O24···H311^i	2.723	H33···H32^xv	2.970
N31···H11^viii	3.525	H211···S1^viii	3.301
N31···H15^v	3.595	H211···F4^vi	3.042
N31···H211^i	3.544	H211···O22^viii	2.575
N32···H6^xi	2.596	H211···O23^viii	2.471
N32···H7^xi	3.504	H211···O24^viii	3.497
N32···H10^iv	3.530	H211···N31^viii	3.544
N32···H11^xii	2.768	H211···C4^viii	3.077
N32···H12^xii	3.075	H211···C5^viii	3.594
N32···H31^xiii	2.829	H211···C6^viii	3.596
N32···H32^xii	3.135	H211···H6^viii	3.507
N32···H32^xiii	3.503	H211···H11^viii	3.570
N32···H33^xii	3.311	H311···S1^viii	3.425
C3···H6^viii	3.376	H311···O22^viii	3.471
C3···H32^xv	3.193	H311···O24^viii	2.723
C4···H211^i	3.077	H311···H11^viii	2.934
C5···H211^i	3.594	H311···H15^v	3.338
O23—S1—O24	118.41 (7)	S1—C13—C18	119.44 (13)
O23—S1—C1	108.25 (7)	C14—C13—C18	120.97 (19)
O23—S1—C13	108.21 (8)	C13—C14—C15	119.1 (2)
O24—S1—C1	105.58 (8)	C14—C15—C16	118.8 (2)
O24—S1—C13	108.01 (8)	F4—C16—C15	118.6 (2)
C1—S1—C13	107.97 (8)	F4—C16—C17	117.9 (2)
C4—N31—C5	127.03 (16)	C15—C16—C17	123.4 (2)
S1—C1—C2	115.64 (11)	C16—C17—C18	118.4 (2)
O21—C2—C1	108.61 (14)	C13—C18—C17	119.29 (17)
O21—C2—C3	111.96 (15)	C2—O21—H211	108.3
O21—C2—C4	109.25 (13)	C4—N31—H311	115.4
C1—C2—C3	109.30 (14)	C5—N31—H311	115.8
C1—C2—C4	109.65 (13)	S1—C1—H11	107.9
C3—C2—C4	108.05 (15)	S1—C1—H12	107.9
O22—C4—N31	124.67 (16)	C2—C1—H11	107.8
O22—C4—C2	120.55 (15)	C2—C1—H12	108.0
N31—C4—C2	114.76 (16)	H11—C1—H12	109.5
N31—C5—C6	123.25 (16)	C2—C3—H31	109.4
N31—C5—C10	117.26 (17)	C2—C3—H32	109.4
C6—C5—C10	119.48 (15)	C2—C3—H33	109.6
C5—C6—C7	119.90 (17)	H31—C3—H32	109.5
C6—C7—C8	120.83 (19)	H31—C3—H33	109.5
C7—C8—C9	119.11 (15)	H32—C3—H33	109.5
C7—C8—C11	119.19 (18)	C5—C6—H6	119.8
C9—C8—C11	121.68 (17)	C7—C6—H6	120.3
C8—C9—C10	120.17 (17)	C6—C7—H7	119.7
C8—C9—C12	120.38 (16)	C8—C7—H7	119.4
C10—C9—C12	119.45 (19)	C5—C10—H10	119.7
C5—C10—C9	120.41 (18)	C9—C10—H10	119.9
N32—C11—C8	178.8 (2)	C13—C14—H14	119.7
F1—C12—F2	107.4 (2)	C15—C14—H14	121.2
F1—C12—F3	106.6 (2)	C14—C15—H15	121.2
F1—C12—C9	112.60 (16)	C16—C15—H15	120.0
F2—C12—F3	104.66 (16)	C16—C17—H17	120.4
F2—C12—C9	112.9 (2)	C18—C17—H17	121.2
F3—C12—C9	112.12 (18)	C13—C18—H18	119.9
S1—C13—C14	119.58 (15)	C17—C18—H18	120.8
O23—S1—C1—C2	29.50 (16)	C5—C6—C7—C8	0.9 (2)
O23—S1—C13—C14	151.24 (13)	C6—C7—C8—C9	2.0 (2)
O23—S1—C13—C18	−27.41 (15)	C6—C7—C8—C11	−176.30 (15)
O24—S1—C1—C2	157.24 (13)	C7—C8—C9—C10	−2.4 (2)
O24—S1—C13—C14	21.92 (16)	C7—C8—C9—C12	177.74 (16)
O24—S1—C13—C18	−156.73 (13)	C11—C8—C9—C10	175.85 (15)
C1—S1—C13—C14	−91.81 (14)	C11—C8—C9—C12	−4.1 (2)
C1—S1—C13—C18	89.55 (14)	C8—C9—C10—C5	−0.1 (2)
C13—S1—C1—C2	−87.43 (15)	C8—C9—C12—F1	−177.35 (17)
C4—N31—C5—C6	−27.9 (2)	C8—C9—C12—F2	60.8 (2)
C4—N31—C5—C10	153.49 (16)	C8—C9—C12—F3	−57.1 (2)
C5—N31—C4—O22	6.2 (2)	C10—C9—C12—F1	2.7 (2)
C5—N31—C4—C2	−175.33 (14)	C10—C9—C12—F2	−119.08 (19)
S1—C1—C2—O21	54.45 (16)	C10—C9—C12—F3	122.97 (19)
S1—C1—C2—C3	176.87 (14)	C12—C9—C10—C5	179.79 (16)
S1—C1—C2—C4	−64.86 (19)	S1—C13—C14—C15	−179.08 (15)
O21—C2—C4—O22	−168.83 (15)	S1—C13—C18—C17	179.05 (14)
O21—C2—C4—N31	12.63 (18)	C14—C13—C18—C17	0.4 (2)
C1—C2—C4—O22	−49.9 (2)	C18—C13—C14—C15	−0.5 (2)
C1—C2—C4—N31	131.55 (15)	C13—C14—C15—C16	0.3 (3)
C3—C2—C4—O22	69.1 (2)	C14—C15—C16—F4	179.69 (19)
C3—C2—C4—N31	−109.40 (17)	C14—C15—C16—C17	−0.1 (3)
N31—C5—C6—C7	177.98 (14)	F4—C16—C17—C18	−179.72 (18)
N31—C5—C10—C9	−178.30 (14)	C15—C16—C17—C18	0.1 (3)
C6—C5—C10—C9	3.0 (2)	C16—C17—C18—C13	−0.2 (2)
C10—C5—C6—C7	−3.4 (2)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z+1; (iv) x, −y+3/2, z+1/2; (v) −x+1, y+1/2, −z+3/2; (vi) −x+1, −y, −z+1; (vii) −x+1, y−1/2, −z+3/2; (viii) x, −y+1/2, z−1/2; (ix) −x, y−1/2, −z+3/2; (x) −x+1, −y, −z+2; (xi) −x, y+1/2, −z+3/2; (xii) x, y+1, z; (xiii) −x, −y+1, −z+1; (xiv) x, y−1, z; (xv) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O21—H211···O23^viii	0.91	2.47	2.856 (2)	106

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