2-(1,3-Benzothia­zol-2-yl­oxy)-N-(4-fluorophen­yl)-N-isopropyl­acetamide

The asymmetric unit of the title compound, C₁₈H₁₇FN₂O₂S, contains two independent mol­ecules related by a pseudo-inversion centre. The mol­ecular packing is stabilized by C—H...O and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.061
• wR factor = 0.150
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C16

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.71 Ratio

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.00 Ratio
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S2     in Main Residue .          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

2-(1,3-Benzothiazol-2-yloxy)-N-(4-fluorophenyl)-N-isopropylacetamide

Crystal data

C18H17FN2O2S	F(000) = 1440
Mr = 344.40	Dx = 1.337 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14205 reflections
a = 17.747 (2) Å	θ = 3.1–27.5°
b = 15.266 (2) Å	µ = 0.21 mm^−1
c = 13.299 (1) Å	T = 293 K
β = 108.243 (6)°	Block, colourless
V = 3422.1 (7) Å^3	0.4 × 0.3 × 0.2 mm
Z = 8

Data collection

Rigaku R-AXIS RAPID IP diffractometer	7827 independent reflections
Radiation source: fine-focus sealed tube	4363 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −23→23
Tmin = 0.909, Tmax = 0.992	k = −19→19
32053 measured reflections	l = −16→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0687P)^2 + 0.4362P] where P = (Fo^2 + 2Fc^2)/3
7827 reflections	(Δ/σ)max = 0.001
433 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.25902 (5)	0.76008 (5)	0.98750 (7)	0.0660 (2)
S2	0.24274 (4)	0.98364 (5)	0.01585 (5)	0.04754 (19)
F1	−0.11615 (11)	0.97715 (11)	0.38931 (14)	0.0750 (5)
F2	0.59917 (11)	0.79028 (13)	0.58494 (14)	0.0823 (6)
N1	0.32557 (14)	0.71301 (15)	0.84528 (18)	0.0527 (6)
N2	0.43945 (13)	1.00847 (14)	0.78043 (16)	0.0485 (5)
N3	0.14873 (13)	1.03699 (15)	0.12088 (16)	0.0487 (5)
N4	0.04102 (12)	0.74454 (13)	0.20820 (16)	0.0427 (5)
O1	0.32362 (14)	0.86256 (13)	0.88185 (18)	0.0777 (7)
O2	0.35013 (17)	1.02617 (15)	0.8673 (2)	0.1043 (10)
O3	0.15753 (11)	0.88568 (12)	0.09778 (14)	0.0558 (5)
O4	0.12811 (13)	0.72211 (13)	0.11743 (16)	0.0672 (6)
C1	0.29738 (14)	0.63757 (17)	0.8807 (2)	0.0456 (6)
C2	0.30419 (17)	0.55337 (19)	0.8449 (2)	0.0573 (7)
H2	0.3295	0.5435	0.7943	0.069*
C3	0.27276 (18)	0.48494 (19)	0.8858 (2)	0.0622 (8)
H3	0.2765	0.4284	0.8618	0.075*
C4	0.23560 (16)	0.49838 (19)	0.9622 (2)	0.0585 (7)
H4	0.2153	0.4507	0.9889	0.070*
C5	0.22840 (15)	0.58090 (19)	0.9989 (2)	0.0520 (7)
H5	0.2034	0.5901	1.0499	0.062*
C6	0.25958 (14)	0.64989 (17)	0.9573 (2)	0.0456 (6)
C7	0.30795 (17)	0.77832 (19)	0.8938 (2)	0.0569 (7)
C8	0.3678 (2)	0.8809 (2)	0.8115 (3)	0.0728 (9)
H8A	0.3373	0.8662	0.7392	0.087*
H8B	0.4169	0.8478	0.8311	0.087*
C9	0.3845 (2)	0.9787 (2)	0.8225 (2)	0.0652 (8)
C10	0.48092 (15)	0.95077 (17)	0.73033 (19)	0.0431 (6)
C11	0.55322 (16)	0.91574 (18)	0.7871 (2)	0.0502 (7)
H11	0.5751	0.9285	0.8587	0.060*
C12	0.59320 (17)	0.86185 (19)	0.7381 (2)	0.0570 (7)
H12	0.6422	0.8381	0.7758	0.068*
C13	0.55949 (17)	0.8439 (2)	0.6328 (2)	0.0556 (7)
C14	0.48840 (17)	0.8770 (2)	0.5750 (2)	0.0604 (8)
H14	0.4667	0.8635	0.5036	0.073*
C15	0.44908 (16)	0.9310 (2)	0.6244 (2)	0.0547 (7)
H15	0.4002	0.9545	0.5858	0.066*
C16	0.45913 (18)	1.10286 (18)	0.7890 (2)	0.0586 (7)
H16	0.4144	1.1342	0.8005	0.070*
C17	0.5301 (3)	1.1187 (3)	0.8826 (4)	0.160 (3)
H17A	0.5209	1.0955	0.9448	0.240*
H17B	0.5397	1.1806	0.8913	0.240*
H17C	0.5753	1.0904	0.8722	0.240*
C18	0.4710 (4)	1.1383 (3)	0.6906 (4)	0.137 (2)
H18A	0.4244	1.1275	0.6315	0.206*
H18B	0.5158	1.1100	0.6787	0.206*
H18C	0.4805	1.2002	0.6981	0.206*
C19	0.18382 (15)	1.11098 (18)	0.09317 (19)	0.0449 (6)
C20	0.17215 (18)	1.1962 (2)	0.1197 (2)	0.0612 (8)
H20	0.1386	1.2083	0.1594	0.073*
C21	0.21071 (19)	1.2628 (2)	0.0869 (3)	0.0666 (8)
H21	0.2032	1.3201	0.1054	0.080*
C22	0.26048 (17)	1.24692 (19)	0.0271 (2)	0.0569 (7)
H22	0.2851	1.2935	0.0048	0.068*
C23	0.27375 (15)	1.16284 (19)	0.0003 (2)	0.0476 (6)
H23	0.3073	1.1516	−0.0396	0.057*
C24	0.23577 (14)	1.09528 (16)	0.03448 (18)	0.0394 (6)
C25	0.17558 (15)	0.96911 (18)	0.08679 (19)	0.0452 (6)
C26	0.10262 (17)	0.87041 (18)	0.1553 (2)	0.0531 (7)
H26A	0.0522	0.8986	0.1202	0.064*
H26B	0.1234	0.8934	0.2266	0.064*
C27	0.09215 (15)	0.77175 (17)	0.15768 (19)	0.0453 (6)
C28	−0.00025 (14)	0.80560 (17)	0.25434 (18)	0.0395 (6)
C29	−0.07352 (15)	0.83726 (17)	0.19655 (19)	0.0463 (6)
H29	−0.0965	0.8196	0.1267	0.056*
C30	−0.11324 (17)	0.89546 (18)	0.2421 (2)	0.0532 (7)
H30	−0.1630	0.9170	0.2039	0.064*
C31	−0.07752 (17)	0.92028 (18)	0.3445 (2)	0.0505 (7)
C32	−0.00530 (17)	0.88983 (19)	0.4038 (2)	0.0552 (7)
H32	0.0173	0.9080	0.4736	0.066*
C33	0.03340 (15)	0.83177 (18)	0.35843 (19)	0.0487 (7)
H33	0.0827	0.8098	0.3979	0.058*
C34	0.02726 (16)	0.64950 (17)	0.2173 (2)	0.0499 (6)
H34	0.0620	0.6179	0.1852	0.060*
C35	−0.05667 (17)	0.62472 (19)	0.1583 (2)	0.0639 (8)
H35A	−0.0692	0.6427	0.0857	0.096*
H35B	−0.0919	0.6532	0.1899	0.096*
H35c	−0.0627	0.5624	0.1614	0.096*
C36	0.0492 (2)	0.6214 (2)	0.3328 (3)	0.0826 (11)
H36A	0.1032	0.6372	0.3689	0.124*
H36B	0.0432	0.5591	0.3365	0.124*
H36C	0.0149	0.6501	0.3657	0.124*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0791 (5)	0.0427 (4)	0.1034 (6)	−0.0051 (4)	0.0676 (5)	−0.0035 (4)
S2	0.0508 (4)	0.0428 (4)	0.0600 (4)	−0.0040 (3)	0.0333 (3)	−0.0049 (3)
F1	0.0981 (13)	0.0576 (12)	0.0892 (12)	0.0100 (10)	0.0580 (11)	−0.0135 (9)
F2	0.0810 (13)	0.0841 (15)	0.1005 (14)	0.0152 (11)	0.0555 (11)	−0.0136 (11)
N1	0.0574 (14)	0.0443 (14)	0.0674 (14)	−0.0019 (11)	0.0355 (12)	−0.0015 (11)
N2	0.0533 (13)	0.0395 (13)	0.0621 (13)	−0.0005 (10)	0.0317 (11)	0.0009 (10)
N3	0.0564 (14)	0.0423 (14)	0.0582 (13)	0.0004 (11)	0.0335 (11)	0.0007 (10)
N4	0.0439 (11)	0.0358 (12)	0.0544 (12)	−0.0026 (9)	0.0238 (10)	−0.0040 (9)
O1	0.1065 (17)	0.0425 (13)	0.1222 (18)	−0.0094 (12)	0.0906 (15)	−0.0024 (11)
O2	0.150 (2)	0.0477 (14)	0.174 (2)	−0.0071 (15)	0.135 (2)	−0.0097 (15)
O3	0.0697 (12)	0.0437 (12)	0.0729 (12)	−0.0101 (9)	0.0496 (10)	−0.0075 (9)
O4	0.0791 (14)	0.0491 (13)	0.0956 (15)	−0.0049 (11)	0.0594 (13)	−0.0121 (11)
C1	0.0371 (13)	0.0420 (16)	0.0584 (16)	−0.0021 (12)	0.0161 (12)	0.0011 (12)
C2	0.0618 (18)	0.0489 (19)	0.0655 (18)	−0.0049 (14)	0.0264 (15)	−0.0072 (13)
C3	0.0657 (19)	0.0410 (17)	0.080 (2)	−0.0074 (15)	0.0233 (16)	−0.0066 (14)
C4	0.0493 (16)	0.0450 (18)	0.082 (2)	−0.0075 (13)	0.0222 (15)	0.0076 (14)
C5	0.0424 (15)	0.0462 (18)	0.0733 (18)	−0.0014 (13)	0.0268 (13)	0.0093 (13)
C6	0.0347 (13)	0.0409 (15)	0.0650 (16)	−0.0019 (11)	0.0210 (12)	0.0012 (12)
C7	0.0611 (18)	0.0458 (18)	0.081 (2)	−0.0037 (14)	0.0464 (16)	0.0031 (14)
C8	0.098 (2)	0.048 (2)	0.103 (2)	−0.0076 (17)	0.075 (2)	−0.0017 (16)
C9	0.085 (2)	0.0456 (18)	0.090 (2)	−0.0013 (16)	0.0628 (18)	0.0003 (15)
C10	0.0426 (14)	0.0419 (17)	0.0512 (16)	−0.0039 (12)	0.0241 (12)	0.0015 (11)
C11	0.0512 (16)	0.0498 (18)	0.0496 (15)	0.0006 (13)	0.0158 (13)	0.0021 (12)
C12	0.0484 (16)	0.0543 (19)	0.0707 (19)	0.0097 (14)	0.0220 (14)	0.0058 (14)
C13	0.0531 (17)	0.0535 (18)	0.073 (2)	−0.0021 (14)	0.0381 (15)	−0.0048 (14)
C14	0.0549 (17)	0.078 (2)	0.0528 (16)	−0.0004 (16)	0.0236 (14)	−0.0082 (14)
C15	0.0427 (15)	0.066 (2)	0.0575 (17)	0.0044 (14)	0.0183 (13)	0.0013 (14)
C16	0.0646 (18)	0.0355 (16)	0.086 (2)	0.0003 (14)	0.0391 (16)	0.0042 (14)
C17	0.124 (4)	0.065 (3)	0.228 (6)	−0.012 (3)	−0.036 (4)	−0.029 (3)
C18	0.229 (6)	0.064 (3)	0.172 (4)	0.018 (3)	0.139 (4)	0.039 (3)
C19	0.0473 (15)	0.0437 (16)	0.0499 (15)	0.0037 (12)	0.0238 (12)	0.0048 (11)
C20	0.073 (2)	0.0484 (19)	0.081 (2)	0.0094 (15)	0.0502 (17)	0.0045 (14)
C21	0.080 (2)	0.0401 (17)	0.096 (2)	0.0118 (15)	0.0517 (19)	0.0096 (15)
C22	0.0615 (18)	0.0432 (17)	0.0764 (19)	0.0028 (14)	0.0368 (16)	0.0127 (14)
C23	0.0415 (14)	0.0507 (17)	0.0563 (16)	0.0027 (12)	0.0238 (12)	0.0078 (12)
C24	0.0370 (13)	0.0406 (15)	0.0421 (13)	0.0023 (11)	0.0147 (11)	0.0021 (10)
C25	0.0482 (15)	0.0459 (17)	0.0487 (14)	−0.0046 (13)	0.0254 (12)	0.0002 (12)
C26	0.0620 (17)	0.0451 (17)	0.0661 (17)	−0.0063 (13)	0.0402 (15)	−0.0046 (13)
C27	0.0485 (15)	0.0421 (16)	0.0512 (15)	−0.0042 (12)	0.0241 (12)	−0.0058 (11)
C28	0.0422 (14)	0.0365 (16)	0.0461 (14)	−0.0050 (11)	0.0228 (12)	−0.0021 (10)
C29	0.0513 (15)	0.0455 (16)	0.0432 (14)	0.0018 (13)	0.0163 (12)	−0.0023 (11)
C30	0.0549 (16)	0.0465 (17)	0.0603 (17)	0.0112 (13)	0.0212 (14)	0.0047 (13)
C31	0.0668 (18)	0.0389 (16)	0.0602 (18)	−0.0009 (14)	0.0406 (15)	−0.0043 (12)
C32	0.0638 (19)	0.0580 (19)	0.0481 (16)	−0.0095 (15)	0.0235 (14)	−0.0110 (13)
C33	0.0455 (15)	0.0533 (18)	0.0482 (15)	−0.0051 (13)	0.0159 (12)	−0.0041 (12)
C34	0.0514 (16)	0.0341 (15)	0.0714 (18)	−0.0019 (12)	0.0297 (14)	−0.0013 (12)
C35	0.0657 (19)	0.052 (2)	0.077 (2)	−0.0179 (15)	0.0266 (16)	−0.0158 (15)
C36	0.093 (3)	0.055 (2)	0.086 (2)	−0.0026 (18)	0.0077 (19)	0.0205 (17)

Geometric parameters (Å, º)

S1—C6	1.730 (3)	C14—H14	0.93
S1—C7	1.749 (3)	C15—H15	0.93
S2—C24	1.732 (3)	C16—C17	1.487 (5)
S2—C25	1.751 (2)	C16—C18	1.492 (4)
F1—C31	1.355 (3)	C16—H16	0.98
F2—C13	1.361 (3)	C17—H17A	0.96
N1—C7	1.279 (3)	C17—H17B	0.96
N1—C1	1.395 (3)	C17—H17C	0.96
N2—C9	1.346 (3)	C18—H18A	0.96
N2—C10	1.438 (3)	C18—H18B	0.96
N2—C16	1.479 (3)	C18—H18C	0.96
N3—C25	1.281 (3)	C19—C20	1.381 (4)
N3—C19	1.394 (3)	C19—C24	1.403 (3)
N4—C27	1.352 (3)	C20—C21	1.371 (4)
N4—C28	1.436 (3)	C20—H20	0.93
N4—C34	1.483 (3)	C21—C22	1.383 (4)
O1—C7	1.336 (3)	C21—H21	0.93
O1—C8	1.424 (3)	C22—C23	1.372 (4)
O2—C9	1.217 (3)	C22—H22	0.93
O3—C25	1.332 (3)	C23—C24	1.384 (4)
O3—C26	1.434 (3)	C23—H23	0.93
O4—C27	1.217 (3)	C26—C27	1.519 (4)
C1—C2	1.389 (4)	C26—H26A	0.97
C1—C6	1.397 (4)	C26—H26B	0.97
C2—C3	1.374 (4)	C28—C29	1.375 (3)
C2—H2	0.93	C28—C33	1.384 (3)
C3—C4	1.389 (4)	C29—C30	1.386 (3)
C3—H3	0.93	C29—H29	0.93
C4—C5	1.371 (4)	C30—C31	1.363 (4)
C4—H4	0.93	C30—H30	0.93
C5—C6	1.383 (4)	C31—C32	1.360 (4)
C5—H5	0.93	C32—C33	1.372 (4)
C8—C9	1.520 (4)	C32—H32	0.93
C8—H8A	0.97	C33—H33	0.93
C8—H8B	0.97	C34—C35	1.499 (4)
C10—C15	1.377 (3)	C34—C36	1.523 (4)
C10—C11	1.377 (3)	C34—H34	0.98
C11—C12	1.376 (4)	C35—H35A	0.96
C11—H11	0.93	C35—H35B	0.96
C12—C13	1.367 (4)	C35—H35c	0.96
C12—H12	0.93	C36—H36A	0.96
C13—C14	1.353 (4)	C36—H36B	0.96
C14—C15	1.373 (4)	C36—H36C	0.96
C6—S1—C7	87.10 (13)	C16—C18—H18A	109.5
C24—S2—C25	87.50 (12)	C16—C18—H18B	109.5
C7—N1—C1	107.6 (2)	H18A—C18—H18B	109.5
C9—N2—C10	121.8 (2)	C16—C18—H18C	109.5
C9—N2—C16	118.8 (2)	H18A—C18—H18C	109.5
C10—N2—C16	119.3 (2)	H18B—C18—H18C	109.5
C25—N3—C19	108.4 (2)	C20—C19—N3	125.5 (2)
C27—N4—C28	121.6 (2)	C20—C19—C24	118.7 (2)
C27—N4—C34	119.6 (2)	N3—C19—C24	115.8 (2)
C28—N4—C34	118.8 (2)	C21—C20—C19	119.2 (3)
C7—O1—C8	116.5 (2)	C21—C20—H20	120.4
C25—O3—C26	116.2 (2)	C19—C20—H20	120.4
C2—C1—N1	124.7 (3)	C20—C21—C22	121.7 (3)
C2—C1—C6	119.2 (3)	C20—C21—H21	119.1
N1—C1—C6	116.1 (2)	C22—C21—H21	119.1
C3—C2—C1	118.6 (3)	C23—C22—C21	120.4 (3)
C3—C2—H2	120.7	C23—C22—H22	119.8
C1—C2—H2	120.7	C21—C22—H22	119.8
C2—C3—C4	121.5 (3)	C22—C23—C24	118.1 (3)
C2—C3—H3	119.3	C22—C23—H23	120.9
C4—C3—H3	119.3	C24—C23—H23	120.9
C5—C4—C3	121.0 (3)	C23—C24—C19	121.9 (2)
C5—C4—H4	119.5	C23—C24—S2	128.5 (2)
C3—C4—H4	119.5	C19—C24—S2	109.67 (19)
C4—C5—C6	117.6 (3)	N3—C25—O3	127.3 (2)
C4—C5—H5	121.2	N3—C25—S2	118.7 (2)
C6—C5—H5	121.2	O3—C25—S2	114.07 (19)
C5—C6—C1	122.2 (3)	O3—C26—C27	106.3 (2)
C5—C6—S1	128.0 (2)	O3—C26—H26A	110.5
C1—C6—S1	109.8 (2)	C27—C26—H26A	110.5
N1—C7—O1	126.7 (3)	O3—C26—H26B	110.5
N1—C7—S1	119.3 (2)	C27—C26—H26B	110.5
O1—C7—S1	114.0 (2)	H26A—C26—H26B	108.7
O1—C8—C9	105.1 (2)	O4—C27—N4	123.6 (2)
O1—C8—H8A	110.7	O4—C27—C26	121.6 (2)
C9—C8—H8A	110.7	N4—C27—C26	114.9 (2)
O1—C8—H8B	110.7	C29—C28—C33	119.6 (2)
C9—C8—H8B	110.7	C29—C28—N4	120.6 (2)
H8A—C8—H8B	108.8	C33—C28—N4	119.8 (2)
O2—C9—N2	122.8 (3)	C28—C29—C30	120.2 (2)
O2—C9—C8	121.3 (3)	C28—C29—H29	119.9
N2—C9—C8	115.9 (2)	C30—C29—H29	119.9
C15—C10—C11	119.3 (3)	C31—C30—C29	118.3 (3)
C15—C10—N2	120.2 (2)	C31—C30—H30	120.9
C11—C10—N2	120.6 (2)	C29—C30—H30	120.9
C12—C11—C10	120.2 (3)	F1—C31—C32	118.6 (2)
C12—C11—H11	119.9	F1—C31—C30	118.4 (3)
C10—C11—H11	119.9	C32—C31—C30	122.9 (3)
C13—C12—C11	118.6 (3)	C31—C32—C33	118.5 (2)
C13—C12—H12	120.7	C31—C32—H32	120.8
C11—C12—H12	120.7	C33—C32—H32	120.8
C14—C13—F2	119.1 (3)	C32—C33—C28	120.5 (3)
C14—C13—C12	122.6 (3)	C32—C33—H33	119.7
F2—C13—C12	118.4 (3)	C28—C33—H33	119.7
C13—C14—C15	118.4 (3)	N4—C34—C35	111.5 (2)
C13—C14—H14	120.8	N4—C34—C36	111.2 (2)
C15—C14—H14	120.8	C35—C34—C36	110.8 (2)
C14—C15—C10	120.9 (3)	N4—C34—H34	107.7
C14—C15—H15	119.5	C35—C34—H34	107.7
C10—C15—H15	119.5	C36—C34—H34	107.7
N2—C16—C17	109.9 (3)	C34—C35—H35A	109.5
N2—C16—C18	112.4 (3)	C34—C35—H35B	109.5
C17—C16—C18	111.1 (4)	H35A—C35—H35B	109.5
N2—C16—H16	107.7	C34—C35—H35c	109.5
C17—C16—H16	107.7	H35A—C35—H35c	109.5
C18—C16—H16	107.7	H35B—C35—H35c	109.5
C16—C17—H17A	109.5	C34—C36—H36A	109.5
C16—C17—H17B	109.5	C34—C36—H36B	109.5
H17A—C17—H17B	109.5	H36A—C36—H36B	109.5
C16—C17—H17C	109.5	C34—C36—H36C	109.5
H17A—C17—H17C	109.5	H36A—C36—H36C	109.5
H17B—C17—H17C	109.5	H36B—C36—H36C	109.5
C7—N1—C1—C2	179.0 (3)	C25—N3—C19—C20	−177.3 (3)
C7—N1—C1—C6	−0.7 (3)	C25—N3—C19—C24	1.9 (3)
N1—C1—C2—C3	−179.2 (3)	N3—C19—C20—C21	−180.0 (3)
C6—C1—C2—C3	0.5 (4)	C24—C19—C20—C21	0.9 (4)
C1—C2—C3—C4	−0.7 (4)	C19—C20—C21—C22	0.6 (5)
C2—C3—C4—C5	0.6 (5)	C20—C21—C22—C23	−1.2 (5)
C3—C4—C5—C6	−0.2 (4)	C21—C22—C23—C24	0.3 (4)
C4—C5—C6—C1	0.0 (4)	C22—C23—C24—C19	1.2 (4)
C4—C5—C6—S1	179.7 (2)	C22—C23—C24—S2	−178.3 (2)
C2—C1—C6—C5	−0.1 (4)	C20—C19—C24—C23	−1.8 (4)
N1—C1—C6—C5	179.6 (2)	N3—C19—C24—C23	179.0 (2)
C2—C1—C6—S1	−179.9 (2)	C20—C19—C24—S2	177.8 (2)
N1—C1—C6—S1	−0.2 (3)	N3—C19—C24—S2	−1.4 (3)
C7—S1—C6—C5	−179.0 (3)	C25—S2—C24—C23	180.0 (2)
C7—S1—C6—C1	0.7 (2)	C25—S2—C24—C19	0.42 (18)
C1—N1—C7—O1	−179.2 (3)	C19—N3—C25—O3	179.3 (2)
C1—N1—C7—S1	1.4 (3)	C19—N3—C25—S2	−1.6 (3)
C8—O1—C7—N1	−3.2 (5)	C26—O3—C25—N3	−0.8 (4)
C8—O1—C7—S1	176.2 (2)	C26—O3—C25—S2	−179.94 (18)
C6—S1—C7—N1	−1.3 (3)	C24—S2—C25—N3	0.7 (2)
C6—S1—C7—O1	179.2 (2)	C24—S2—C25—O3	179.94 (19)
C7—O1—C8—C9	−173.9 (3)	C25—O3—C26—C27	−179.6 (2)
C10—N2—C9—O2	178.3 (3)	C28—N4—C27—O4	−179.9 (2)
C16—N2—C9—O2	0.1 (5)	C34—N4—C27—O4	0.6 (4)
C10—N2—C9—C8	−1.4 (4)	C28—N4—C27—C26	0.7 (3)
C16—N2—C9—C8	−179.5 (3)	C34—N4—C27—C26	−178.8 (2)
O1—C8—C9—O2	−13.0 (5)	O3—C26—C27—O4	1.3 (3)
O1—C8—C9—N2	166.7 (3)	O3—C26—C27—N4	−179.3 (2)
C9—N2—C10—C15	87.4 (3)	C27—N4—C28—C29	90.9 (3)
C16—N2—C10—C15	−94.4 (3)	C34—N4—C28—C29	−89.5 (3)
C9—N2—C10—C11	−93.5 (3)	C27—N4—C28—C33	−90.1 (3)
C16—N2—C10—C11	84.6 (3)	C34—N4—C28—C33	89.4 (3)
C15—C10—C11—C12	0.3 (4)	C33—C28—C29—C30	0.4 (4)
N2—C10—C11—C12	−178.8 (2)	N4—C28—C29—C30	179.3 (2)
C10—C11—C12—C13	−0.2 (4)	C28—C29—C30—C31	0.4 (4)
C11—C12—C13—C14	0.0 (5)	C29—C30—C31—F1	180.0 (2)
C11—C12—C13—F2	−179.7 (3)	C29—C30—C31—C32	−0.7 (4)
F2—C13—C14—C15	180.0 (3)	F1—C31—C32—C33	179.5 (2)
C12—C13—C14—C15	0.3 (5)	C30—C31—C32—C33	0.2 (4)
C13—C14—C15—C10	−0.3 (5)	C31—C32—C33—C28	0.6 (4)
C11—C10—C15—C14	0.0 (4)	C29—C28—C33—C32	−0.9 (4)
N2—C10—C15—C14	179.1 (3)	N4—C28—C33—C32	−179.8 (2)
C9—N2—C16—C17	95.3 (4)	C27—N4—C34—C35	−115.4 (3)
C10—N2—C16—C17	−82.9 (4)	C28—N4—C34—C35	65.0 (3)
C9—N2—C16—C18	−140.4 (4)	C27—N4—C34—C36	120.3 (3)
C10—N2—C16—C18	41.4 (4)	C28—N4—C34—C36	−59.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O2^i	0.93	2.52	3.289 (4)	140
C12—H12···Cg1^ii	0.93	2.70	3.573 (3)	156
C15—H15···Cg2^iii	0.93	2.70	3.509 (3)	146
C29—H29···Cg1^iv	0.93	2.78	3.617 (3)	151

Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+2, −z+1; (iii) x, −y+3/2, z−1/2; (iv) −x, −y+2, −z.