4-[4-(4-Chloro-benzo-yl)-2,3-diphenyl-isoxazolidin-5-yl]-1-(4-meth-oxy-phen-yl)-3-phenyl-azetidin-2-one.

In the title compound, C(38)H(31)ClN(2)O(4), the isoxazole ring adopts an envelope conformation with the N atom as the flap. The crystal packing is stabilized by C-H⋯O hydrogen bonds, forming chains running along the c-axis direction.

Related literature

For general background to β-lactams, see: Jones et al. (1989 ▶); Brakhage (1998 ▶); Banik & Becker (2000 ▶). For a related structure, see: Sundaramoorthy et al. (2012 ▶).

Experimental

Crystal data

C38H31ClN2O4

M = 615.10

Monoclinic,

a = 10.1221 (10) Å

b = 17.4890 (17) Å

c = 17.7421 (18) Å

β = 98.150 (6)°

V = 3109.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.951, T max = 0.967

23486 measured reflections

5491 independent reflections

3214 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.132

S = 0.99

5491 reflections

407 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812038123/bt6829sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038123/bt6829Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038123/bt6829Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C38H31ClN2O4	F(000) = 1288
Mr = 615.10	Dx = 1.314 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7716 reflections
a = 10.1221 (10) Å	θ = 1.6–28.4°
b = 17.4890 (17) Å	µ = 0.17 mm−1
c = 17.7421 (18) Å	T = 293 K
β = 98.150 (6)°	Block, colourless
V = 3109.1 (5) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	5491 independent reflections
Radiation source: fine-focus sealed tube	3214 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ω and φ scans	θmax = 25.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→11
Tmin = 0.951, Tmax = 0.967	k = −20→19
23486 measured reflections	l = −21→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0566P)2 + 0.7516P] where P = (Fo2 + 2Fc2)/3
5491 reflections	(Δ/σ)max < 0.001
407 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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. 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
C1	0.1235 (4)	0.56910 (18)	0.92991 (18)	0.0952 (11)
H1A	0.1944	0.6030	0.9211	0.143*
H1B	0.0490	0.5985	0.9417	0.143*
H1C	0.0966	0.5391	0.8851	0.143*
C2	0.2637 (3)	0.46709 (15)	0.98273 (15)	0.0641 (7)
C3	0.3357 (3)	0.46562 (15)	0.92296 (15)	0.0671 (8)
H3	0.3218	0.5028	0.8852	0.080*
C4	0.4285 (3)	0.40889 (15)	0.91917 (14)	0.0623 (7)
H4	0.4782	0.4085	0.8789	0.075*
C5	0.4491 (2)	0.35290 (13)	0.97360 (13)	0.0490 (6)
C6	0.3775 (3)	0.35466 (16)	1.03403 (14)	0.0639 (7)
H6	0.3914	0.3174	1.0718	0.077*
C7	0.2856 (3)	0.41155 (17)	1.03833 (15)	0.0748 (8)
H7	0.2374	0.4127	1.0792	0.090*
C8	0.5786 (2)	0.24964 (13)	0.90286 (12)	0.0473 (6)
H8	0.6073	0.2821	0.8632	0.057*
C9	0.6982 (2)	0.21662 (14)	0.95941 (13)	0.0531 (6)
H9	0.7803	0.2432	0.9515	0.064*
C10	0.6345 (2)	0.25842 (15)	1.02071 (14)	0.0567 (6)
C11	0.7257 (2)	0.13271 (15)	0.96688 (13)	0.0549 (6)
C12	0.8284 (3)	0.10087 (19)	0.93330 (15)	0.0781 (9)
H12	0.8795	0.1319	0.9062	0.094*
C13	0.8558 (4)	0.0236 (2)	0.9396 (2)	0.1023 (12)
H13	0.9246	0.0029	0.9166	0.123*
C14	0.7824 (5)	−0.0220 (2)	0.9795 (2)	0.1094 (13)
H14	0.8021	−0.0738	0.9842	0.131*
C15	0.6803 (4)	0.0074 (2)	1.0126 (2)	0.0951 (10)
H15	0.6295	−0.0244	1.0392	0.114*
C16	0.6521 (3)	0.08535 (18)	1.00663 (16)	0.0729 (8)
H16	0.5829	0.1055	1.0298	0.087*
C17	0.4693 (2)	0.19375 (13)	0.87231 (12)	0.0433 (5)
H17	0.4398	0.1668	0.9154	0.052*
C18	0.3478 (2)	0.23073 (13)	0.82526 (11)	0.0426 (5)
H18	0.3732	0.2817	0.8093	0.051*
C19	0.3247 (2)	0.17755 (14)	0.75339 (12)	0.0470 (6)
H19	0.2896	0.2083	0.7089	0.056*
C20	0.5419 (2)	0.20436 (14)	0.71008 (13)	0.0490 (6)
C21	0.4897 (3)	0.25163 (16)	0.65020 (14)	0.0638 (7)
H21	0.3981	0.2527	0.6341	0.077*
C22	0.5739 (3)	0.29695 (18)	0.61468 (17)	0.0814 (9)
H22	0.5386	0.3287	0.5748	0.098*
C23	0.7086 (3)	0.29552 (19)	0.63755 (19)	0.0838 (9)
H23	0.7648	0.3266	0.6138	0.101*
C24	0.7602 (3)	0.24798 (18)	0.69571 (17)	0.0747 (8)
H24	0.8520	0.2467	0.7110	0.090*
C25	0.6786 (2)	0.20225 (16)	0.73171 (14)	0.0608 (7)
H25	0.7151	0.1698	0.7707	0.073*
C26	0.2310 (2)	0.11091 (14)	0.75998 (12)	0.0483 (6)
C27	0.2709 (3)	0.04226 (16)	0.79247 (16)	0.0697 (8)
H27	0.3607	0.0343	0.8106	0.084*
C28	0.1794 (3)	−0.01581 (17)	0.79888 (17)	0.0771 (8)
H28	0.2083	−0.0619	0.8215	0.092*
C29	0.0477 (3)	−0.00560 (18)	0.77219 (16)	0.0706 (8)
H29	−0.0138	−0.0442	0.7769	0.085*
C30	0.0075 (3)	0.06236 (19)	0.73840 (17)	0.0786 (8)
H30	−0.0821	0.0699	0.7196	0.094*
C31	0.0981 (3)	0.11970 (17)	0.73199 (15)	0.0685 (7)
H31	0.0690	0.1653	0.7083	0.082*
C32	0.2290 (2)	0.23887 (14)	0.86813 (13)	0.0489 (6)
C33	0.1259 (2)	0.29713 (13)	0.84202 (14)	0.0522 (6)
C34	0.1156 (2)	0.33164 (15)	0.77096 (16)	0.0642 (7)
H34	0.1747	0.3178	0.7377	0.077*
C35	0.0194 (3)	0.38610 (16)	0.74874 (19)	0.0758 (8)
H35	0.0127	0.4082	0.7007	0.091*
C36	−0.0656 (3)	0.40701 (16)	0.7980 (2)	0.0777 (9)
C37	−0.0583 (3)	0.37409 (19)	0.8685 (2)	0.0842 (9)
H37	−0.1172	0.3890	0.9015	0.101*
C38	0.0370 (3)	0.31840 (16)	0.89081 (16)	0.0698 (8)
H38	0.0412	0.2955	0.9384	0.084*
N1	0.54326 (19)	0.29368 (11)	0.96857 (10)	0.0519 (5)
N2	0.45940 (18)	0.15261 (11)	0.74562 (10)	0.0497 (5)
O1	0.1687 (2)	0.52014 (13)	0.99171 (11)	0.0979 (7)
O2	0.65372 (19)	0.26133 (11)	1.08976 (10)	0.0793 (6)
O3	0.51966 (15)	0.13785 (9)	0.82304 (8)	0.0513 (4)
O4	0.21907 (18)	0.19892 (11)	0.92295 (10)	0.0692 (5)
Cl1	−0.18375 (10)	0.47664 (6)	0.77110 (7)	0.1308 (4)

	U11	U22	U33	U12	U13	U23
C1	0.113 (3)	0.078 (2)	0.091 (2)	0.039 (2)	0.005 (2)	0.0199 (19)
C2	0.0778 (18)	0.0607 (18)	0.0536 (16)	0.0226 (14)	0.0088 (14)	−0.0012 (14)
C3	0.096 (2)	0.0519 (17)	0.0545 (16)	0.0145 (15)	0.0133 (15)	0.0090 (13)
C4	0.0837 (19)	0.0566 (17)	0.0489 (15)	0.0082 (15)	0.0170 (13)	0.0030 (13)
C5	0.0548 (14)	0.0471 (15)	0.0430 (13)	0.0035 (12)	0.0000 (11)	−0.0054 (12)
C6	0.0723 (18)	0.0700 (18)	0.0498 (15)	0.0125 (15)	0.0099 (13)	0.0132 (14)
C7	0.084 (2)	0.091 (2)	0.0535 (16)	0.0277 (17)	0.0215 (14)	0.0107 (16)
C8	0.0481 (13)	0.0491 (14)	0.0438 (13)	0.0020 (11)	0.0033 (10)	−0.0010 (11)
C9	0.0403 (13)	0.0650 (17)	0.0508 (14)	−0.0004 (12)	−0.0042 (10)	−0.0040 (13)
C10	0.0537 (15)	0.0605 (17)	0.0512 (16)	0.0007 (12)	−0.0091 (12)	−0.0105 (13)
C11	0.0495 (14)	0.0650 (18)	0.0457 (14)	0.0104 (13)	−0.0084 (11)	−0.0058 (13)
C12	0.080 (2)	0.095 (2)	0.0580 (17)	0.0271 (18)	0.0027 (14)	−0.0005 (16)
C13	0.122 (3)	0.106 (3)	0.077 (2)	0.060 (3)	0.004 (2)	−0.007 (2)
C14	0.148 (4)	0.080 (3)	0.092 (3)	0.039 (3)	−0.014 (3)	−0.007 (2)
C15	0.112 (3)	0.075 (3)	0.091 (2)	0.000 (2)	−0.010 (2)	0.019 (2)
C16	0.0710 (19)	0.075 (2)	0.0696 (19)	0.0076 (16)	0.0004 (15)	0.0054 (16)
C17	0.0471 (13)	0.0475 (14)	0.0350 (11)	0.0047 (11)	0.0050 (9)	−0.0009 (11)
C18	0.0419 (12)	0.0458 (14)	0.0396 (12)	0.0019 (10)	0.0037 (9)	0.0001 (10)
C19	0.0415 (12)	0.0592 (15)	0.0387 (12)	0.0030 (11)	0.0005 (9)	0.0007 (11)
C20	0.0489 (14)	0.0538 (15)	0.0451 (13)	−0.0039 (12)	0.0098 (11)	−0.0106 (12)
C21	0.0522 (15)	0.0765 (19)	0.0610 (16)	−0.0079 (14)	0.0027 (12)	0.0081 (15)
C22	0.073 (2)	0.093 (2)	0.079 (2)	−0.0151 (17)	0.0104 (16)	0.0232 (18)
C23	0.069 (2)	0.090 (2)	0.096 (2)	−0.0198 (17)	0.0265 (18)	0.008 (2)
C24	0.0476 (15)	0.094 (2)	0.084 (2)	−0.0071 (15)	0.0167 (15)	−0.0120 (19)
C25	0.0465 (14)	0.0752 (19)	0.0613 (16)	0.0064 (13)	0.0101 (12)	−0.0069 (14)
C26	0.0502 (14)	0.0548 (16)	0.0397 (13)	−0.0016 (12)	0.0052 (10)	−0.0042 (12)
C27	0.0583 (16)	0.0639 (19)	0.084 (2)	−0.0020 (15)	−0.0022 (14)	−0.0003 (16)
C28	0.083 (2)	0.0572 (19)	0.089 (2)	−0.0065 (16)	0.0047 (17)	0.0030 (16)
C29	0.0679 (19)	0.076 (2)	0.0694 (18)	−0.0208 (16)	0.0155 (15)	−0.0064 (16)
C30	0.0526 (16)	0.091 (2)	0.090 (2)	−0.0152 (17)	0.0039 (15)	0.0075 (19)
C31	0.0534 (16)	0.077 (2)	0.0726 (18)	−0.0081 (14)	−0.0015 (13)	0.0103 (15)
C32	0.0526 (14)	0.0484 (15)	0.0466 (14)	−0.0005 (11)	0.0094 (11)	−0.0017 (12)
C33	0.0432 (13)	0.0490 (15)	0.0646 (16)	0.0015 (11)	0.0087 (11)	−0.0039 (13)
C34	0.0509 (15)	0.0632 (18)	0.0787 (19)	0.0096 (13)	0.0103 (13)	0.0086 (15)
C35	0.0585 (17)	0.0674 (19)	0.099 (2)	0.0093 (15)	0.0019 (16)	0.0116 (17)
C36	0.0550 (17)	0.0597 (19)	0.114 (3)	0.0115 (14)	−0.0048 (17)	−0.0134 (19)
C37	0.0585 (18)	0.089 (2)	0.107 (3)	0.0188 (17)	0.0163 (17)	−0.027 (2)
C38	0.0583 (16)	0.077 (2)	0.0760 (18)	0.0093 (15)	0.0149 (14)	−0.0115 (16)
N1	0.0569 (12)	0.0550 (13)	0.0407 (11)	0.0073 (10)	−0.0040 (9)	−0.0063 (10)
N2	0.0462 (11)	0.0620 (13)	0.0387 (10)	0.0027 (10)	−0.0020 (8)	−0.0027 (9)
O1	0.1229 (18)	0.1013 (17)	0.0726 (13)	0.0604 (15)	0.0244 (12)	0.0142 (12)
O2	0.0865 (13)	0.0973 (15)	0.0458 (11)	0.0217 (11)	−0.0194 (9)	−0.0177 (10)
O3	0.0540 (9)	0.0556 (10)	0.0408 (8)	0.0124 (8)	−0.0055 (7)	−0.0049 (8)
O4	0.0768 (12)	0.0724 (13)	0.0636 (11)	0.0104 (10)	0.0279 (9)	0.0149 (10)
Cl1	0.0894 (7)	0.1048 (8)	0.1876 (11)	0.0526 (6)	−0.0169 (6)	−0.0139 (7)

C1—O1	1.415 (3)	C18—H18	0.9800
C1—H1A	0.9600	C19—N2	1.457 (3)
C1—H1B	0.9600	C19—C26	1.517 (3)
C1—H1C	0.9600	C19—H19	0.9800
C2—O1	1.362 (3)	C20—C25	1.383 (3)
C2—C3	1.369 (3)	C20—C21	1.390 (3)
C2—C7	1.380 (4)	C20—N2	1.436 (3)
C3—C4	1.375 (3)	C21—C22	1.380 (4)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.370 (3)	C22—C23	1.367 (4)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.377 (3)	C23—C24	1.370 (4)
C5—N1	1.419 (3)	C23—H23	0.9300
C6—C7	1.372 (4)	C24—C25	1.371 (4)
C6—H6	0.9300	C24—H24	0.9300
C7—H7	0.9300	C25—H25	0.9300
C8—N1	1.483 (3)	C26—C27	1.368 (3)
C8—C17	1.518 (3)	C26—C31	1.375 (3)
C8—C9	1.569 (3)	C27—C28	1.390 (4)
C8—H8	0.9800	C27—H27	0.9300
C9—C11	1.496 (3)	C28—C29	1.362 (4)
C9—C10	1.527 (3)	C28—H28	0.9300
C9—H9	0.9800	C29—C30	1.367 (4)
C10—O2	1.214 (3)	C29—H29	0.9300
C10—N1	1.359 (3)	C30—C31	1.375 (4)
C11—C16	1.374 (4)	C30—H30	0.9300
C11—C12	1.386 (4)	C31—H31	0.9300
C12—C13	1.381 (4)	C32—O4	1.213 (3)
C12—H12	0.9300	C32—C33	1.485 (3)
C13—C14	1.355 (5)	C33—C38	1.385 (3)
C13—H13	0.9300	C33—C34	1.388 (3)
C14—C15	1.360 (5)	C34—C35	1.379 (4)
C14—H14	0.9300	C34—H34	0.9300
C15—C16	1.394 (4)	C35—C36	1.360 (4)
C15—H15	0.9300	C35—H35	0.9300
C16—H16	0.9300	C36—C37	1.370 (4)
C17—O3	1.451 (2)	C36—Cl1	1.726 (3)
C17—C18	1.529 (3)	C37—C38	1.389 (4)
C17—H17	0.9800	C37—H37	0.9300
C18—C32	1.518 (3)	C38—H38	0.9300
C18—C19	1.569 (3)	N2—O3	1.445 (2)
O1—C1—H1A	109.5	N2—C19—C18	102.75 (16)
O1—C1—H1B	109.5	C26—C19—C18	114.55 (17)
H1A—C1—H1B	109.5	N2—C19—H19	109.0
O1—C1—H1C	109.5	C26—C19—H19	109.0
H1A—C1—H1C	109.5	C18—C19—H19	109.0
H1B—C1—H1C	109.5	C25—C20—C21	119.0 (2)
O1—C2—C3	124.4 (2)	C25—C20—N2	118.8 (2)
O1—C2—C7	116.1 (2)	C21—C20—N2	121.9 (2)
C3—C2—C7	119.4 (2)	C22—C21—C20	119.9 (2)
C2—C3—C4	119.6 (2)	C22—C21—H21	120.1
C2—C3—H3	120.2	C20—C21—H21	120.1
C4—C3—H3	120.2	C23—C22—C21	120.6 (3)
C5—C4—C3	121.2 (2)	C23—C22—H22	119.7
C5—C4—H4	119.4	C21—C22—H22	119.7
C3—C4—H4	119.4	C22—C23—C24	119.5 (3)
C4—C5—C6	119.3 (2)	C22—C23—H23	120.2
C4—C5—N1	120.9 (2)	C24—C23—H23	120.2
C6—C5—N1	119.8 (2)	C23—C24—C25	120.9 (3)
C7—C6—C5	119.7 (2)	C23—C24—H24	119.5
C7—C6—H6	120.2	C25—C24—H24	119.5
C5—C6—H6	120.2	C24—C25—C20	120.0 (3)
C6—C7—C2	120.8 (2)	C24—C25—H25	120.0
C6—C7—H7	119.6	C20—C25—H25	120.0
C2—C7—H7	119.6	C27—C26—C31	117.7 (2)
N1—C8—C17	111.74 (18)	C27—C26—C19	123.8 (2)
N1—C8—C9	86.49 (16)	C31—C26—C19	118.4 (2)
C17—C8—C9	116.66 (19)	C26—C27—C28	121.0 (3)
N1—C8—H8	113.1	C26—C27—H27	119.5
C17—C8—H8	113.1	C28—C27—H27	119.5
C9—C8—H8	113.1	C29—C28—C27	120.4 (3)
C11—C9—C10	119.9 (2)	C29—C28—H28	119.8
C11—C9—C8	122.33 (19)	C27—C28—H28	119.8
C10—C9—C8	85.07 (17)	C28—C29—C30	118.8 (3)
C11—C9—H9	109.1	C28—C29—H29	120.6
C10—C9—H9	109.1	C30—C29—H29	120.6
C8—C9—H9	109.1	C29—C30—C31	120.7 (3)
O2—C10—N1	131.6 (2)	C29—C30—H30	119.7
O2—C10—C9	135.7 (2)	C31—C30—H30	119.7
N1—C10—C9	92.71 (19)	C30—C31—C26	121.3 (3)
C16—C11—C12	118.2 (3)	C30—C31—H31	119.4
C16—C11—C9	121.9 (2)	C26—C31—H31	119.4
C12—C11—C9	119.8 (3)	O4—C32—C33	120.7 (2)
C13—C12—C11	120.8 (3)	O4—C32—C18	120.6 (2)
C13—C12—H12	119.6	C33—C32—C18	118.7 (2)
C11—C12—H12	119.6	C38—C33—C34	118.6 (2)
C14—C13—C12	120.0 (3)	C38—C33—C32	118.6 (2)
C14—C13—H13	120.0	C34—C33—C32	122.7 (2)
C12—C13—H13	120.0	C35—C34—C33	121.3 (3)
C13—C14—C15	120.7 (4)	C35—C34—H34	119.4
C13—C14—H14	119.7	C33—C34—H34	119.4
C15—C14—H14	119.7	C36—C35—C34	119.2 (3)
C14—C15—C16	119.7 (4)	C36—C35—H35	120.4
C14—C15—H15	120.1	C34—C35—H35	120.4
C16—C15—H15	120.1	C35—C36—C37	121.1 (3)
C11—C16—C15	120.6 (3)	C35—C36—Cl1	119.3 (3)
C11—C16—H16	119.7	C37—C36—Cl1	119.6 (3)
C15—C16—H16	119.7	C36—C37—C38	120.0 (3)
O3—C17—C8	110.41 (17)	C36—C37—H37	120.0
O3—C17—C18	106.27 (16)	C38—C37—H37	120.0
C8—C17—C18	114.33 (18)	C33—C38—C37	119.8 (3)
O3—C17—H17	108.6	C33—C38—H38	120.1
C8—C17—H17	108.6	C37—C38—H38	120.1
C18—C17—H17	108.6	C10—N1—C5	133.33 (19)
C32—C18—C17	113.52 (18)	C10—N1—C8	94.76 (18)
C32—C18—C19	115.19 (17)	C5—N1—C8	131.89 (18)
C17—C18—C19	102.05 (17)	C20—N2—O3	109.67 (16)
C32—C18—H18	108.6	C20—N2—C19	117.59 (18)
C17—C18—H18	108.6	O3—N2—C19	103.78 (15)
C19—C18—H18	108.6	C2—O1—C1	118.5 (2)
N2—C19—C26	112.38 (19)	N2—O3—C17	108.38 (15)
O1—C2—C3—C4	−179.4 (3)	C18—C19—C26—C31	93.9 (3)
C7—C2—C3—C4	0.0 (4)	C31—C26—C27—C28	−1.8 (4)
C2—C3—C4—C5	1.0 (4)	C19—C26—C27—C28	178.0 (2)
C3—C4—C5—C6	−1.5 (4)	C26—C27—C28—C29	0.5 (4)
C3—C4—C5—N1	178.8 (2)	C27—C28—C29—C30	0.6 (4)
C4—C5—C6—C7	0.9 (4)	C28—C29—C30—C31	−0.5 (4)
N1—C5—C6—C7	−179.4 (2)	C29—C30—C31—C26	−0.8 (4)
C5—C6—C7—C2	0.1 (4)	C27—C26—C31—C30	1.9 (4)
O1—C2—C7—C6	178.9 (3)	C19—C26—C31—C30	−177.9 (2)
C3—C2—C7—C6	−0.6 (5)	C17—C18—C32—O4	−21.7 (3)
N1—C8—C9—C11	129.4 (2)	C19—C18—C32—O4	95.4 (3)
C17—C8—C9—C11	16.8 (3)	C17—C18—C32—C33	157.8 (2)
N1—C8—C9—C10	6.87 (17)	C19—C18—C32—C33	−85.1 (3)
C17—C8—C9—C10	−105.7 (2)	O4—C32—C33—C38	15.7 (4)
C11—C9—C10—O2	47.9 (4)	C18—C32—C33—C38	−163.8 (2)
C8—C9—C10—O2	172.6 (3)	O4—C32—C33—C34	−164.9 (2)
C11—C9—C10—N1	−132.2 (2)	C18—C32—C33—C34	15.6 (3)
C8—C9—C10—N1	−7.50 (18)	C38—C33—C34—C35	0.0 (4)
C10—C9—C11—C16	27.0 (3)	C32—C33—C34—C35	−179.4 (2)
C8—C9—C11—C16	−77.3 (3)	C33—C34—C35—C36	1.0 (4)
C10—C9—C11—C12	−152.7 (2)	C34—C35—C36—C37	−1.0 (5)
C8—C9—C11—C12	103.0 (3)	C34—C35—C36—Cl1	178.6 (2)
C16—C11—C12—C13	0.1 (4)	C35—C36—C37—C38	0.1 (5)
C9—C11—C12—C13	179.8 (3)	Cl1—C36—C37—C38	−179.6 (2)
C11—C12—C13—C14	−0.4 (5)	C34—C33—C38—C37	−1.0 (4)
C12—C13—C14—C15	0.9 (6)	C32—C33—C38—C37	178.4 (2)
C13—C14—C15—C16	−1.1 (5)	C36—C37—C38—C33	1.0 (4)
C12—C11—C16—C15	−0.2 (4)	O2—C10—N1—C5	9.2 (5)
C9—C11—C16—C15	−179.9 (2)	C9—C10—N1—C5	−170.7 (2)
C14—C15—C16—C11	0.7 (5)	O2—C10—N1—C8	−172.1 (3)
N1—C8—C17—O3	−164.49 (16)	C9—C10—N1—C8	7.93 (19)
C9—C8—C17—O3	−67.2 (2)	C4—C5—N1—C10	139.2 (3)
N1—C8—C17—C18	75.8 (2)	C6—C5—N1—C10	−40.5 (4)
C9—C8—C17—C18	173.01 (18)	C4—C5—N1—C8	−39.0 (4)
O3—C17—C18—C32	135.15 (18)	C6—C5—N1—C8	141.3 (2)
C8—C17—C18—C32	−102.8 (2)	C17—C8—N1—C10	109.6 (2)
O3—C17—C18—C19	10.6 (2)	C9—C8—N1—C10	−7.72 (19)
C8—C17—C18—C19	132.61 (18)	C17—C8—N1—C5	−71.7 (3)
C32—C18—C19—N2	−155.04 (19)	C9—C8—N1—C5	170.9 (2)
C17—C18—C19—N2	−31.6 (2)	C25—C20—N2—O3	31.7 (3)
C32—C18—C19—C26	−32.9 (3)	C21—C20—N2—O3	−154.0 (2)
C17—C18—C19—C26	90.6 (2)	C25—C20—N2—C19	149.9 (2)
C25—C20—C21—C22	−1.6 (4)	C21—C20—N2—C19	−35.8 (3)
N2—C20—C21—C22	−176.0 (2)	C26—C19—N2—C20	156.22 (18)
C20—C21—C22—C23	0.4 (4)	C18—C19—N2—C20	−80.1 (2)
C21—C22—C23—C24	0.7 (5)	C26—C19—N2—O3	−82.5 (2)
C22—C23—C24—C25	−0.5 (5)	C18—C19—N2—O3	41.1 (2)
C23—C24—C25—C20	−0.8 (4)	C3—C2—O1—C1	11.6 (5)
C21—C20—C25—C24	1.9 (4)	C7—C2—O1—C1	−167.9 (3)
N2—C20—C25—C24	176.3 (2)	C20—N2—O3—C17	90.60 (19)
N2—C19—C26—C27	30.9 (3)	C19—N2—O3—C17	−35.8 (2)
C18—C19—C26—C27	−85.9 (3)	C8—C17—O3—N2	−109.89 (18)
N2—C19—C26—C31	−149.3 (2)	C18—C17—O3—N2	14.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O2i	0.98	2.41	3.338 (3)	158
C21—H21···O2i	0.93	2.50	3.425 (4)	173
C37—H37···O1ii	0.93	2.58	3.407 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O2i	0.98	2.41	3.338 (3)	158
C21—H21⋯O2i	0.93	2.50	3.425 (4)	173
C37—H37⋯O1ii	0.93	2.58	3.407 (4)	148

Symmetry codes: (i) ; (ii) .