5-[5-(4-Methoxy­phenyl)-3-tri­fluoro­methyl-1H-pyrazol-1-yl]-2-sulfamoyl­benzyl propionate: a novel 1,5-dirayl­pyrazole class of COX-2 inhibitor

The title compound, C₂₁H₂₀F₃N₃O₅S, has been made during our research program on COX-2 inhibitors. The mol­ecules are held together by intermolecular hydrogen bonds involving the amide N atom with the unsubstituted N atom of the pyrazole ring and with an O atom of the sulfan­amide group, across centers of symmetry.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.058
• wR factor = 0.088
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.79
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced ..........          ?
PLAT156_ALERT_4_C Axial System Input Cell not Standard ...........          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C21

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

(I)

Crystal data

C21H20F3N3O5S	Z = 2
Mr = 483.46	F(000) = 500.00
Triclinic, P1	Dx = 1.493 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.5418 Å
a = 10.4490 (8) Å	Cell parameters from 25 reflections
b = 12.0126 (8) Å	θ = 22.7–24.6°
c = 9.2196 (9) Å	µ = 1.94 mm^−1
α = 111.068 (6)°	T = 298 K
β = 94.851 (7)°	Block, colorless
γ = 86.328 (6)°	0.50 × 0.50 × 0.40 mm
V = 1075.3 (2) Å^3

Data collection

Rigaku AFC-7S diffractometer	Rint = 0.051
ω–2θ scans	θmax = 68.0°
Absorption correction: ψ scan (North et al., 1968)	h = −12→12
Tmin = 0.346, Tmax = 0.461	k = −13→14
4902 measured reflections	l = −11→4
3926 independent reflections	3 standard reflections every 150 reflections
3801 reflections with F^2 > 2σ(F^2)	intensity decay: 2.6%

Refinement

Refinement on F	weighting by Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979): 232.809, 288.588, 57.8579
R[F^2 > 2σ(F^2)] = 0.058	(Δ/σ)max = 0.010
wR(F^2) = 0.088	Δρmax = 0.41 e Å^−3
S = 1.04	Δρmin = −0.35 e Å^−3
3854 reflections	Extinction correction: Larson (1970) (equation 22)
325 parameters	Extinction coefficient: 416 (22)
H atoms treated by a mixture of independent and constrained refinement

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement using reflections with F² > 1.0 σ(F²). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative 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	0.18380 (5)	0.50840 (5)	0.66650 (6)	0.0382 (2)
F1	0.8874 (2)	0.1482 (2)	0.1314 (3)	0.0891 (8)
F2	0.8443 (2)	−0.0226 (2)	−0.0309 (2)	0.0769 (6)
F3	0.9287 (2)	−0.0067 (3)	0.1899 (3)	0.0923 (10)
O1	0.0637 (2)	0.4506 (2)	0.6258 (2)	0.0515 (6)
O2	0.2303 (2)	0.5540 (2)	0.8257 (2)	0.0541 (6)
O3	0.62240 (10)	0.48760 (10)	0.7610 (2)	0.0456 (5)
O4	0.6274 (2)	0.6555 (2)	0.9685 (3)	0.0666 (6)
O5	0.1156 (2)	−0.2392 (2)	0.3089 (3)	0.0655 (6)
N1	0.1731 (3)	0.6152 (2)	0.6023 (3)	0.0524 (8)
N2	0.5485 (2)	0.1316 (2)	0.2981 (2)	0.0355 (5)
N3	0.6629 (2)	0.1594 (2)	0.2621 (2)	0.0388 (6)
C1	0.3001 (2)	0.4023 (2)	0.5599 (3)	0.0331 (6)
C2	0.4310 (2)	0.4039 (2)	0.6095 (2)	0.0337 (6)
C3	0.5121 (2)	0.3134 (2)	0.5203 (3)	0.0350 (6)
C4	0.4639 (2)	0.2267 (2)	0.3838 (2)	0.0338 (6)
C5	0.3364 (2)	0.2294 (2)	0.3317 (3)	0.0386 (6)
C6	0.2544 (2)	0.3165 (2)	0.4222 (3)	0.0385 (6)
C7	0.4847 (2)	0.4983 (2)	0.7569 (3)	0.0427 (6)
C8	0.6835 (2)	0.5741 (2)	0.8778 (3)	0.0390 (6)
C9	0.8258 (2)	0.5535 (2)	0.8770 (3)	0.0472 (6)
C10	0.9007 (3)	0.6567 (3)	0.9823 (5)	0.0771 (12)
C11	0.5291 (2)	0.0110 (2)	0.2389 (3)	0.0364 (6)
C12	0.6359 (2)	−0.0411 (2)	0.1589 (3)	0.0423 (6)
C13	0.7139 (2)	0.0538 (2)	0.1772 (3)	0.0396 (6)
C14	0.4189 (2)	−0.0486 (2)	0.2641 (3)	0.0363 (6)
C15	0.3527 (2)	−0.0061 (2)	0.3991 (3)	0.0379 (6)
C16	0.2506 (2)	−0.0669 (2)	0.4177 (3)	0.0412 (6)
C17	0.2146 (2)	−0.1728 (2)	0.3008 (3)	0.0446 (6)
C18	0.2826 (3)	−0.2183 (2)	0.1676 (3)	0.0505 (8)
C19	0.3826 (3)	−0.1570 (2)	0.1495 (3)	0.0453 (6)
C20	0.0217 (3)	−0.1832 (3)	0.4141 (4)	0.0625 (12)
C21	0.8434 (2)	0.0449 (2)	0.1169 (3)	0.0450 (6)
H1	0.6006	0.3104	0.5527	0.040*
H2	0.3060	0.1724	0.2353	0.044*
H3	0.1659	0.3183	0.3893	0.044*
H4	0.4551	0.4878	0.8456	0.046*
H5	0.4577	0.5753	0.7566	0.046*
H6	0.8468	0.4866	0.9075	0.054*
H7	0.8501	0.5360	0.7740	0.054*
H8	0.9900	0.6370	0.9749	0.081*
H9	0.8808	0.7245	0.9535	0.082*
H10	0.8791	0.6741	1.0864	0.082*
H11	0.6532	−0.1237	0.1045	0.048*
H12	0.3782	0.0654	0.4803	0.043*
H13	0.2050	−0.0360	0.5096	0.048*
H14	0.2584	−0.2911	0.0880	0.056*
H15	0.4289	−0.1892	0.0582	0.051*
H16	0.0608	−0.1542	0.5170	0.077*
H17	−0.0187	−0.1185	0.3895	0.077*
H18	−0.0407	−0.2393	0.4073	0.077*
H19	0.115 (4)	0.611 (3)	0.531 (5)	0.070 (10)*
H20	0.226 (3)	0.671 (3)	0.644 (4)	0.062 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0296 (4)	0.0354 (4)	0.0413 (4)	−0.0024 (2)	0.0072 (2)	0.0024 (3)
F1	0.0770 (10)	0.0500 (10)	0.129 (2)	−0.0149 (9)	0.0570 (10)	0.0050 (10)
F2	0.0650 (10)	0.0880 (10)	0.0540 (10)	−0.0110 (10)	0.0285 (8)	−0.0102 (9)
F3	0.0500 (10)	0.146 (2)	0.098 (2)	0.0200 (10)	0.0180 (10)	0.065 (2)
O1	0.0337 (9)	0.0480 (10)	0.0660 (10)	−0.0080 (7)	0.0111 (8)	0.0092 (9)
O2	0.0440 (10)	0.0640 (10)	0.0400 (10)	0.0033 (8)	0.0107 (7)	0.0003 (8)
O3	0.0309 (8)	0.0418 (9)	0.0459 (9)	−0.0047 (7)	0.0025 (7)	−0.0068 (7)
O4	0.0460 (10)	0.0560 (10)	0.0630 (10)	−0.0041 (9)	0.0025 (9)	−0.0210 (10)
O5	0.0640 (10)	0.0440 (10)	0.0800 (10)	−0.0232 (9)	0.0200 (10)	0.0050 (10)
N1	0.0480 (10)	0.0350 (10)	0.067 (2)	−0.0055 (9)	−0.0060 (10)	0.0110 (10)
N2	0.0360 (10)	0.0296 (9)	0.0348 (9)	−0.0035 (7)	0.0088 (7)	0.0022 (7)
N3	0.0390 (10)	0.0340 (10)	0.0380 (10)	−0.0043 (8)	0.0113 (8)	0.0040 (8)
C1	0.0320 (10)	0.0290 (10)	0.0360 (10)	−0.0009 (8)	0.0056 (8)	0.0082 (8)
C2	0.0340 (10)	0.0310 (10)	0.0320 (10)	−0.0039 (8)	0.0059 (8)	0.0049 (8)
C3	0.0310 (10)	0.0330 (10)	0.0360 (10)	−0.0037 (8)	0.0047 (8)	0.0053 (9)
C4	0.0380 (10)	0.0270 (10)	0.0320 (10)	−0.0013 (8)	0.0079 (8)	0.0038 (8)
C5	0.0420 (10)	0.0350 (10)	0.0320 (10)	−0.0042 (9)	−0.0010 (9)	0.0041 (9)
C6	0.0360 (10)	0.0380 (10)	0.0360 (10)	−0.0013 (9)	−0.0002 (9)	0.0072 (9)
C7	0.0320 (10)	0.0410 (10)	0.0410 (10)	−0.0022 (9)	0.0049 (9)	−0.0030 (10)
C8	0.0400 (10)	0.0340 (10)	0.0340 (10)	−0.0043 (9)	0.0024 (9)	0.0009 (9)
C9	0.0390 (10)	0.0420 (10)	0.0530 (10)	−0.0030 (10)	0.0010 (10)	0.0080 (10)
C10	0.045 (2)	0.070 (2)	0.089 (2)	−0.0140 (10)	−0.012 (2)	−0.003 (2)
C11	0.0410 (10)	0.0290 (10)	0.0330 (10)	−0.0046 (8)	0.0057 (9)	0.0024 (8)
C12	0.0450 (10)	0.0320 (10)	0.0420 (10)	−0.0029 (9)	0.0110 (10)	0.0017 (9)
C13	0.0410 (10)	0.0360 (10)	0.0360 (10)	−0.0023 (9)	0.0115 (9)	0.0036 (9)
C14	0.0380 (10)	0.0320 (10)	0.0350 (10)	−0.0034 (9)	0.0042 (9)	0.0066 (9)
C15	0.0410 (10)	0.0320 (10)	0.0350 (10)	−0.0050 (9)	0.0030 (9)	0.0044 (9)
C16	0.0430 (10)	0.0350 (10)	0.0420 (10)	−0.0045 (9)	0.0070 (10)	0.0080 (10)
C17	0.0440 (10)	0.0350 (10)	0.0520 (10)	−0.0100 (10)	0.0020 (10)	0.0110 (10)
C18	0.057 (2)	0.0330 (10)	0.0490 (10)	−0.0120 (10)	0.0030 (10)	−0.0020 (10)
C19	0.0510 (10)	0.0350 (10)	0.0410 (10)	−0.0040 (10)	0.0090 (10)	0.0010 (10)
C20	0.061 (2)	0.055 (2)	0.075 (2)	−0.0180 (10)	0.0170 (10)	0.0220 (10)
C21	0.0430 (10)	0.0400 (10)	0.0440 (10)	−0.0030 (10)	0.0160 (10)	0.0020 (10)

Geometric parameters (Å, º)

S1—O1	1.429 (2)	C11—C14	1.471 (3)
S1—O2	1.4233 (18)	C12—C13	1.396 (3)
S1—N1	1.589 (3)	C13—C21	1.489 (3)
S1—C1	1.780 (2)	C14—C19	1.401 (4)
F1—C21	1.309 (4)	C14—C15	1.390 (3)
F2—C21	1.312 (3)	C15—C16	1.386 (3)
F3—C21	1.326 (4)	C16—C17	1.389 (4)
O3—C7	1.435 (2)	C17—C18	1.388 (4)
O3—C8	1.346 (3)	C18—C19	1.371 (4)
O4—C8	1.192 (3)	C3—H1	0.950
O5—C17	1.369 (3)	C5—H2	0.950
O5—C20	1.401 (4)	C6—H3	0.950
N2—N3	1.360 (3)	C7—H4	0.950
N2—C4	1.432 (3)	C7—H5	0.951
N2—C11	1.374 (4)	C9—H6	0.950
N3—C13	1.333 (3)	C9—H7	0.949
N1—H19	0.85 (4)	C10—H8	0.950
N1—H20	0.85 (4)	C10—H9	0.949
C1—C2	1.404 (3)	C10—H10	0.950
C1—C6	1.386 (4)	C12—H11	0.950
C2—C7	1.514 (3)	C15—H12	0.950
C2—C3	1.390 (3)	C16—H13	0.950
C3—C4	1.393 (3)	C18—H14	0.950
C4—C5	1.380 (3)	C19—H15	0.950
C5—C6	1.380 (3)	C20—H16	0.950
C8—C9	1.492 (3)	C20—H17	0.950
C9—C10	1.491 (5)	C20—H18	0.950
C11—C12	1.378 (3)
S1···H4	3.199	C6···H7^i	3.054
S1···H5	2.990	C11···H2	2.941
F1···N3	2.701 (3)	C12···H15	2.770
F1···N1^i	3.086 (4)	C13···H13^v	3.018
F2···F3^ii	2.994 (3)	C14···H12^v	3.087
F3···F2^ii	2.994 (3)	C14···H2	2.926
F1···H20^i	2.69 (4)	C15···H12^v	3.072
F2···H2^iii	2.584	C15···H2	3.031
F3···H17^iv	2.646	C16···H17	2.890
F3···H16^v	2.697	C16···H16	2.671
O1···C9^vi	3.405 (3)	C17···H1^v	3.007
O1···N1^vii	3.057 (4)	C19···H11	2.965
O1···C20^viii	3.273 (4)	C20···H13	2.569
O1···O1^vii	3.133 (3)	H1···O3	2.307
O2···C7	2.769 (3)	H1···N3	2.746
O2···C18^ix	3.379 (3)	H1···C17^v	3.007
O4···C19^ix	3.418 (4)	H2···C11	2.941
O1···H18^viii	2.470	H2···C14	2.926
O1···H19^vii	2.25 (4)	H2···C15	3.031
O1···H7^vi	2.667	H2···F2^iii	2.584
O1···H3	2.471	H3···O1	2.471
O2···H5	2.563	H4···S1	3.199
O2···H8^vi	2.910	H4···O2	2.445
O2···H4	2.445	H4···O4	2.657
O2···H6^x	2.861	H5···S1	2.990
O2···H14^ix	2.472	H5···O2	2.563
O3···H1	2.307	H5···O4	2.484
O4···H4	2.657	H6···O2^x	2.861
O4···H5	2.484	H7···O1^iv	2.667
O4···H9	2.853	H7···C6^i	3.054
O4···H10	2.751	H8···O2^iv	2.910
O4···H11^ix	2.515	H9···O4	2.853
O4···H15^ix	2.674	H10···O4	2.751
N1···F1^i	3.086 (4)	H11···O4^xi	2.515
N1···O1^vii	3.057 (4)	H11···C19	2.965
N1···N3^i	3.103 (4)	H11···H15	2.474
N3···N1^i	3.103 (4)	H12···N2	2.875
N3···F1	2.701 (3)	H12···C4	2.635
N2···H12	2.875	H12···C5	2.771
N3···H1	2.746	H12···C14^v	3.087
N3···H20^i	2.26 (4)	H12···C15^v	3.072
C4···C15	3.149 (3)	H13···C20	2.569
C5···C14	3.242 (4)	H13···H16	2.157
C5···C15	3.099 (4)	H13···H17	2.597
C5···C8^i	3.535 (4)	H13···C13^v	3.018
C6···C8^i	3.581 (4)	H13···H17^viii	2.589
C7···O2	2.769 (3)	H14···O2^xi	2.472
C8···C6^i	3.581 (4)	H15···O4^xi	2.674
C8···C5^i	3.535 (4)	H15···C12	2.770
C9···O1^iv	3.405 (3)	H15···H11	2.474
C11···C15^v	3.479 (4)	H16···C16	2.671
C14···C5	3.242 (4)	H16···H13	2.157
C15···C4	3.149 (3)	H16···F3^v	2.697
C15···C11^v	3.479 (4)	H17···F3^vi	2.646
C15···C5	3.099 (4)	H17···C16	2.890
C15···C15^v	3.443 (3)	H17···H13	2.597
C18···O2^xi	3.379 (3)	H17···H13^viii	2.589
C19···O4^xi	3.418 (4)	H18···O1^viii	2.470
C20···O1^viii	3.273 (4)	H19···O1^vii	2.25 (4)
C4···H12	2.635	H20···F1^i	2.69 (3)
C5···H12	2.771	H20···N3^i	2.26 (4)
O1—S1—O2	119.29 (12)	C17—C18—C19	120.0 (2)
O1—S1—N1	107.09 (15)	C14—C19—C18	121.2 (2)
O1—S1—C1	106.10 (12)	F1—C21—C13	113.6 (2)
O2—S1—N1	108.20 (14)	F2—C21—C13	111.9 (2)
O2—S1—C1	108.20 (12)	F3—C21—C13	110.9 (2)
N1—S1—C1	107.41 (14)	F2—C21—F3	105.3 (2)
C7—O3—C8	115.09 (17)	F1—C21—F2	107.2 (2)
C17—O5—C20	118.2 (3)	F1—C21—F3	107.6 (2)
N3—N2—C4	118.6 (2)	C2—C3—H1	120.0
N3—N2—C11	112.6 (2)	C4—C3—H1	119.8
C4—N2—C11	128.7 (2)	C4—C5—H2	120.5
N2—N3—C13	103.5 (2)	C6—C5—H2	120.8
S1—N1—H20	117 (2)	C1—C6—H3	119.6
H19—N1—H20	127 (4)	C5—C6—H3	119.7
S1—N1—H19	116 (3)	O3—C7—H4	110.0
S1—C1—C2	122.98 (18)	O3—C7—H5	109.2
S1—C1—C6	116.07 (16)	C2—C7—H4	110.0
C2—C1—C6	120.9 (2)	C2—C7—H5	109.5
C3—C2—C7	119.75 (19)	H4—C7—H5	109.4
C1—C2—C3	117.9 (2)	C8—C9—H6	107.7
C1—C2—C7	122.3 (2)	C8—C9—H7	108.4
C2—C3—C4	120.2 (2)	C10—C9—H6	108.8
N2—C4—C3	118.92 (19)	C10—C9—H7	107.9
N2—C4—C5	119.63 (19)	H6—C9—H7	109.4
C3—C4—C5	121.4 (2)	C9—C10—H8	109.5
C4—C5—C6	118.7 (2)	C9—C10—H9	109.9
C1—C6—C5	120.7 (2)	C9—C10—H10	109.0
O3—C7—C2	108.61 (19)	H8—C10—H9	109.4
O3—C8—C9	111.5 (2)	H8—C10—H10	109.4
O3—C8—O4	122.4 (2)	H9—C10—H10	109.5
O4—C8—C9	126.0 (2)	C11—C12—H11	127.5
C8—C9—C10	114.5 (2)	C13—C12—H11	127.6
N2—C11—C12	105.9 (2)	C14—C15—H12	119.5
N2—C11—C14	126.1 (2)	C16—C15—H12	119.4
C12—C11—C14	127.9 (2)	C15—C16—H13	120.2
C11—C12—C13	104.9 (2)	C17—C16—H13	120.1
N3—C13—C12	113.0 (2)	C17—C18—H14	119.8
N3—C13—C21	120.6 (2)	C19—C18—H14	120.1
C12—C13—C21	126.4 (2)	C14—C19—H15	119.4
C11—C14—C15	123.4 (2)	C18—C19—H15	119.4
C15—C14—C19	118.1 (2)	O5—C20—H16	109.5
C11—C14—C19	118.4 (2)	O5—C20—H17	109.7
C14—C15—C16	121.0 (2)	O5—C20—H18	109.2
C15—C16—C17	119.7 (2)	H16—C20—H17	109.5
O5—C17—C16	123.9 (2)	H16—C20—H18	109.5
O5—C17—C18	116.2 (2)	H17—C20—H18	109.5
C16—C17—C18	119.8 (2)
O1—S1—C1—C2	−153.9 (2)	C1—C2—C3—C4	1.9 (4)
O1—S1—C1—C6	26.4 (2)	C2—C3—C4—C5	1.4 (4)
O2—S1—C1—C2	−24.8 (3)	C2—C3—C4—N2	−177.2 (2)
O2—S1—C1—C6	155.5 (2)	C3—C4—C5—C6	−3.6 (4)
N1—S1—C1—C2	91.8 (2)	N2—C4—C5—C6	175.1 (2)
N1—S1—C1—C6	−87.9 (2)	C4—C5—C6—C1	2.4 (4)
C8—O3—C7—C2	173.32 (19)	O4—C8—C9—C10	−11.6 (4)
C7—O3—C8—C9	177.8 (2)	O3—C8—C9—C10	168.6 (2)
C7—O3—C8—O4	−2.1 (4)	C12—C11—C14—C15	145.7 (3)
C20—O5—C17—C18	−161.4 (3)	C12—C11—C14—C19	−31.0 (4)
C20—O5—C17—C16	20.1 (4)	N2—C11—C12—C13	0.5 (3)
N3—N2—C4—C5	130.6 (2)	C14—C11—C12—C13	−176.7 (2)
N3—N2—C4—C3	−50.7 (3)	N2—C11—C14—C15	−30.9 (4)
N3—N2—C11—C12	−0.9 (3)	N2—C11—C14—C19	152.3 (3)
C11—N2—C4—C3	132.0 (3)	C11—C12—C13—C21	177.9 (2)
C11—N2—C4—C5	−46.7 (3)	C11—C12—C13—N3	0.0 (3)
C11—N2—N3—C13	0.9 (3)	N3—C13—C21—F1	−11.5 (4)
C4—N2—N3—C13	−176.84 (19)	C12—C13—C21—F2	49.3 (4)
C4—N2—C11—C14	−6.2 (4)	C12—C13—C21—F3	−67.9 (4)
N3—N2—C11—C14	176.4 (2)	N3—C13—C21—F3	109.8 (3)
C4—N2—C11—C12	176.6 (2)	C12—C13—C21—F1	170.8 (3)
N2—N3—C13—C12	−0.5 (3)	N3—C13—C21—F2	−133.0 (3)
N2—N3—C13—C21	−178.5 (2)	C11—C14—C15—C16	−179.0 (2)
S1—C1—C2—C3	177.21 (19)	C19—C14—C15—C16	−2.3 (4)
S1—C1—C2—C7	−1.4 (3)	C11—C14—C19—C18	178.5 (2)
C2—C1—C6—C5	1.0 (4)	C15—C14—C19—C18	1.6 (4)
C6—C1—C2—C3	−3.1 (4)	C14—C15—C16—C17	0.9 (4)
C6—C1—C2—C7	178.3 (2)	C15—C16—C17—C18	1.3 (4)
S1—C1—C6—C5	−179.3 (2)	C15—C16—C17—O5	179.7 (2)
C7—C2—C3—C4	−179.5 (2)	C16—C17—C18—C19	−1.9 (4)
C1—C2—C7—O3	−170.3 (2)	O5—C17—C18—C19	179.5 (3)
C3—C2—C7—O3	11.1 (3)	C17—C18—C19—C14	0.5 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H19···O1^vii	0.85 (4)	2.25 (4)	3.057 (4)	159 (4)
N1—H20···N3^i	0.85 (4)	2.26 (4)	3.103 (4)	169 (3)
C3—H1···O3	0.95	2.31	2.678 (3)	103
C6—H3···O1	0.95	2.47	2.852 (3)	104
C7—H4···O2	0.95	2.45	2.769 (3)	100
C12—H11···O4^xi	0.95	2.52	3.433 (4)	163
C18—H14···O2^xi	0.95	2.47	3.379 (3)	160
C20—H18···O1^viii	0.95	2.47	3.273 (4)	142

Symmetry codes: (i) −x+1, −y+1, −z+1; (vii) −x, −y+1, −z+1; (viii) −x, −y, −z+1; (xi) x, y−1, z−1.