{(1R,3S)-2-Benzyl-6,7-dimeth-oxy-1-phenyl-1,2,3,4-tetra-hydro-isoquinolin-3-yl}diphenyl-methanol.

In the title compound, C(37)H(35)NO(3), a precursor to novel chiral catalysts, the N-containing six-membered ring assumes a half-chair conformation. Inter-molecular C-H⋯O hydrogen bonds link the mol-ecules in the crystal structure.

Related literature

For the synthesis of the title compound, see: Chakka et al. (2010 ▶). For related structures, see: Aubry et al. (2006 ▶). For a related structure with the same chiral centres and configuration, see: Naicker et al. (2009 ▶). For proline diaryl alcohols, see: Diner et al. (2008 ▶); Seebach et al. (2008 ▶).

Experimental

Crystal data

C37H35NO3

M = 541.66

Monoclinic,

a = 11.9706 (5) Å

b = 10.1934 (4) Å

c = 13.1515 (5) Å

β = 116.546 (2)°

V = 1435.58 (10) Å3

Z = 2

Cu Kα radiation

μ = 0.62 mm−1

T = 173 K

0.22 × 0.14 × 0.12 mm

Data collection

Bruker Kappa Duo APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.876, T max = 0.930

15262 measured reflections

2514 independent reflections

2451 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.068

S = 1.10

2514 reflections

375 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810005295/lx2135sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005295/lx2135Isup2.hkl

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

C37H35NO3	F(000) = 576
Mr = 541.66	Dx = 1.253 Mg m−3
Monoclinic, P21	Melting point: 478 K
Hall symbol: P 2yb	Cu Kα radiation, λ = 1.54184 Å
a = 11.9706 (5) Å	Cell parameters from 15260 reflections
b = 10.1934 (4) Å	θ = 4.1–64.1°
c = 13.1515 (5) Å	µ = 0.62 mm−1
β = 116.546 (2)°	T = 173 K
V = 1435.58 (10) Å3	Needle, light-yellow
Z = 2	0.22 × 0.14 × 0.12 mm

Bruker Kappa Duo APEXII diffractometer	2514 independent reflections
Radiation source: fine-focus sealed tube	2451 reflections with I > 2σ(I)
graphite	Rint = 0.025
0.5° φ scans and ω scans	θmax = 64.1°, θmin = 4.1°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −13→13
Tmin = 0.876, Tmax = 0.930	k = −11→11
15262 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.068	w = 1/[σ2(Fo2) + (0.0394P)2 + 0.1556P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2514 reflections	Δρmax = 0.14 e Å−3
375 parameters	Δρmin = −0.12 e Å−3
1 restraint	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0019 (4)

Experimental. Half sphere of data collected using SAINT strategy (Bruker, 2006). Crystal to detector distance = 50 mm; combination of φ and ω scans of 0.5°, 70 s per °, 2 iterations.

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 > 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.

	x	y	z	Uiso*/Ueq
O1	0.22854 (13)	0.26734 (16)	1.12303 (10)	0.0431 (3)
O2	0.04675 (14)	0.12697 (17)	0.98256 (12)	0.0500 (4)
O3	0.05661 (12)	0.42417 (16)	0.44410 (11)	0.0404 (3)
H3O	−0.004 (3)	0.362 (3)	0.413 (2)	0.075 (9)*
N1	0.25806 (13)	0.46610 (15)	0.69414 (12)	0.0293 (3)
C1	0.32465 (16)	0.43732 (19)	0.81717 (14)	0.0301 (4)
H1	0.3345	0.5232	0.8571	0.036*
C2	0.24903 (16)	0.34980 (18)	0.85715 (15)	0.0308 (4)
C3	0.27894 (17)	0.34611 (19)	0.97314 (15)	0.0329 (4)
H3	0.3486	0.3948	1.0255	0.040*
C4	0.20987 (17)	0.2737 (2)	1.01278 (15)	0.0346 (4)
C5	0.10937 (17)	0.1980 (2)	0.93545 (16)	0.0366 (4)
C6	0.08020 (17)	0.2006 (2)	0.82194 (15)	0.0348 (4)
H6	0.0123	0.1494	0.7702	0.042*
C7	0.14841 (16)	0.27720 (19)	0.78076 (15)	0.0315 (4)
C8	0.10892 (16)	0.2823 (2)	0.65460 (15)	0.0327 (4)
H8A	0.0316	0.3350	0.6169	0.039*
H8B	0.0906	0.1924	0.6229	0.039*
C9	0.21113 (16)	0.34278 (18)	0.63028 (14)	0.0294 (4)
H9	0.2827	0.2798	0.6612	0.035*
C10	0.17522 (16)	0.35837 (19)	0.50136 (15)	0.0310 (4)
C11	0.16612 (15)	0.22675 (19)	0.44078 (15)	0.0307 (4)
C12	0.19679 (17)	0.1051 (2)	0.49339 (15)	0.0339 (4)
H12	0.2266	0.0994	0.5734	0.041*
C13	0.18466 (18)	−0.0085 (2)	0.43084 (18)	0.0384 (4)
H13	0.2054	−0.0910	0.4683	0.046*
C14	0.14278 (19)	−0.0023 (2)	0.31498 (18)	0.0409 (5)
H14	0.1338	−0.0802	0.2724	0.049*
C15	0.11407 (19)	0.1175 (2)	0.26129 (16)	0.0434 (5)
H15	0.0862	0.1227	0.1815	0.052*
C16	0.12580 (18)	0.2302 (2)	0.32337 (16)	0.0394 (5)
H16	0.1059	0.3123	0.2853	0.047*
C17	0.27291 (17)	0.44212 (19)	0.48694 (14)	0.0334 (4)
C18	0.2411 (2)	0.5509 (2)	0.41693 (18)	0.0489 (5)
H18	0.1563	0.5780	0.3789	0.059*
C19	0.3321 (3)	0.6211 (3)	0.4016 (2)	0.0626 (7)
H19	0.3091	0.6952	0.3527	0.075*
C20	0.4552 (3)	0.5837 (3)	0.4569 (2)	0.0636 (7)
H20	0.5172	0.6317	0.4463	0.076*
C21	0.4880 (2)	0.4767 (3)	0.5273 (2)	0.0553 (6)
H21	0.5729	0.4504	0.5656	0.066*
C22	0.39822 (18)	0.4074 (2)	0.54256 (18)	0.0409 (5)
H22	0.4224	0.3340	0.5923	0.049*
C23	0.45677 (16)	0.38930 (19)	0.84700 (14)	0.0314 (4)
C24	0.50143 (18)	0.2662 (2)	0.89154 (16)	0.0392 (4)
H24	0.4496	0.2076	0.9075	0.047*
C25	0.6210 (2)	0.2279 (2)	0.9130 (2)	0.0513 (5)
H25	0.6500	0.1428	0.9424	0.062*
C26	0.6982 (2)	0.3123 (3)	0.8920 (2)	0.0532 (6)
H26	0.7797	0.2852	0.9058	0.064*
C27	0.65631 (19)	0.4367 (3)	0.85060 (19)	0.0526 (6)
H27	0.7097	0.4966	0.8381	0.063*
C28	0.53601 (18)	0.4734 (2)	0.82747 (18)	0.0447 (5)
H28	0.5071	0.5583	0.7975	0.054*
C29	0.3369 (2)	0.3293 (3)	1.20594 (16)	0.0490 (5)
H29A	0.3399	0.3181	1.2811	0.074*
H29B	0.3344	0.4230	1.1885	0.074*
H29C	0.4112	0.2896	1.2055	0.074*
C30	−0.0409 (2)	0.0329 (3)	0.9135 (2)	0.0639 (7)
H30A	−0.0784	−0.0106	0.9573	0.096*
H30B	0.0012	−0.0324	0.8880	0.096*
H30C	−0.1064	0.0765	0.8473	0.096*
C31	0.16184 (17)	0.5677 (2)	0.67155 (17)	0.0359 (4)
H31A	0.1115	0.5449	0.7117	0.043*
H31B	0.1052	0.5709	0.5891	0.043*
C32	0.22097 (17)	0.7003 (2)	0.71081 (16)	0.0391 (5)
C33	0.1997 (2)	0.7730 (3)	0.7892 (2)	0.0552 (6)
H33	0.1479	0.7391	0.8206	0.066*
C34	0.2552 (3)	0.8977 (3)	0.8222 (2)	0.0750 (9)
H34	0.2416	0.9479	0.8765	0.090*
C35	0.3287 (3)	0.9462 (3)	0.7760 (2)	0.0765 (9)
H35	0.3647	1.0310	0.7973	0.092*
C36	0.3507 (2)	0.8743 (3)	0.6998 (2)	0.0637 (7)
H36	0.4025	0.9088	0.6686	0.076*
C37	0.2985 (2)	0.7520 (2)	0.66755 (19)	0.0495 (5)
H37	0.3156	0.7021	0.6151	0.059*

	U11	U22	U33	U12	U13	U23
O1	0.0513 (8)	0.0493 (8)	0.0319 (6)	−0.0119 (7)	0.0214 (6)	−0.0048 (6)
O2	0.0593 (9)	0.0570 (10)	0.0414 (7)	−0.0261 (8)	0.0294 (7)	−0.0056 (7)
O3	0.0328 (7)	0.0446 (8)	0.0367 (7)	0.0091 (7)	0.0094 (5)	0.0015 (7)
N1	0.0304 (7)	0.0272 (8)	0.0309 (7)	−0.0005 (6)	0.0143 (6)	0.0002 (6)
C1	0.0332 (9)	0.0264 (9)	0.0315 (8)	−0.0034 (8)	0.0154 (7)	−0.0028 (8)
C2	0.0342 (9)	0.0278 (9)	0.0335 (9)	−0.0016 (8)	0.0179 (7)	−0.0032 (8)
C3	0.0372 (9)	0.0308 (10)	0.0325 (8)	−0.0048 (8)	0.0171 (7)	−0.0061 (8)
C4	0.0431 (10)	0.0336 (10)	0.0317 (8)	−0.0012 (9)	0.0209 (8)	−0.0022 (8)
C5	0.0419 (10)	0.0360 (11)	0.0384 (9)	−0.0066 (9)	0.0239 (8)	−0.0022 (9)
C6	0.0363 (9)	0.0347 (10)	0.0359 (9)	−0.0082 (8)	0.0185 (8)	−0.0058 (8)
C7	0.0341 (9)	0.0292 (9)	0.0348 (9)	−0.0022 (8)	0.0184 (7)	−0.0037 (8)
C8	0.0340 (9)	0.0334 (10)	0.0324 (9)	−0.0038 (8)	0.0164 (7)	−0.0041 (8)
C9	0.0306 (8)	0.0272 (9)	0.0320 (9)	0.0002 (7)	0.0153 (7)	−0.0010 (7)
C10	0.0299 (9)	0.0320 (10)	0.0321 (9)	0.0035 (8)	0.0146 (7)	0.0032 (8)
C11	0.0274 (8)	0.0360 (10)	0.0326 (9)	−0.0043 (8)	0.0169 (7)	−0.0012 (8)
C12	0.0354 (9)	0.0362 (10)	0.0313 (9)	0.0015 (8)	0.0160 (7)	−0.0006 (8)
C13	0.0367 (10)	0.0337 (11)	0.0480 (11)	0.0005 (8)	0.0218 (9)	−0.0014 (9)
C14	0.0415 (10)	0.0444 (12)	0.0462 (11)	−0.0106 (9)	0.0281 (9)	−0.0145 (9)
C15	0.0504 (11)	0.0527 (13)	0.0334 (9)	−0.0138 (11)	0.0245 (9)	−0.0082 (10)
C16	0.0465 (10)	0.0420 (12)	0.0331 (9)	−0.0069 (9)	0.0208 (8)	0.0017 (9)
C17	0.0421 (10)	0.0290 (10)	0.0332 (8)	−0.0022 (8)	0.0206 (8)	−0.0022 (8)
C18	0.0616 (13)	0.0418 (12)	0.0446 (11)	0.0023 (11)	0.0248 (10)	0.0105 (10)
C19	0.100 (2)	0.0388 (13)	0.0616 (14)	−0.0096 (14)	0.0470 (14)	0.0111 (12)
C20	0.0764 (18)	0.0510 (16)	0.0845 (18)	−0.0174 (13)	0.0548 (15)	0.0012 (14)
C21	0.0490 (12)	0.0551 (15)	0.0755 (16)	−0.0087 (12)	0.0401 (12)	−0.0028 (13)
C22	0.0422 (10)	0.0355 (11)	0.0525 (11)	0.0002 (9)	0.0278 (9)	0.0036 (9)
C23	0.0319 (9)	0.0327 (10)	0.0274 (8)	−0.0035 (8)	0.0113 (7)	−0.0033 (7)
C24	0.0394 (10)	0.0300 (10)	0.0444 (10)	−0.0043 (9)	0.0154 (8)	−0.0038 (9)
C25	0.0447 (11)	0.0395 (12)	0.0604 (13)	0.0066 (10)	0.0151 (10)	−0.0008 (10)
C26	0.0353 (10)	0.0587 (16)	0.0612 (14)	0.0057 (11)	0.0174 (10)	−0.0032 (12)
C27	0.0374 (11)	0.0624 (16)	0.0598 (13)	−0.0038 (11)	0.0233 (10)	0.0089 (13)
C28	0.0377 (10)	0.0435 (12)	0.0524 (11)	−0.0004 (9)	0.0197 (9)	0.0118 (10)
C29	0.0525 (12)	0.0600 (14)	0.0337 (10)	−0.0104 (11)	0.0185 (9)	−0.0055 (10)
C30	0.0733 (16)	0.0710 (18)	0.0550 (13)	−0.0382 (15)	0.0354 (12)	−0.0082 (13)
C31	0.0318 (9)	0.0307 (10)	0.0434 (10)	0.0024 (8)	0.0152 (8)	−0.0016 (8)
C32	0.0346 (9)	0.0282 (10)	0.0416 (10)	0.0059 (8)	0.0057 (8)	0.0012 (9)
C33	0.0553 (13)	0.0428 (13)	0.0526 (12)	0.0115 (11)	0.0108 (10)	−0.0074 (11)
C34	0.093 (2)	0.0450 (16)	0.0549 (14)	0.0174 (15)	0.0041 (14)	−0.0155 (12)
C35	0.0830 (19)	0.0335 (14)	0.0658 (16)	−0.0077 (13)	−0.0091 (14)	0.0039 (13)
C36	0.0584 (14)	0.0397 (13)	0.0640 (15)	−0.0079 (11)	0.0014 (11)	0.0134 (12)
C37	0.0462 (11)	0.0364 (12)	0.0537 (12)	0.0007 (10)	0.0113 (9)	0.0092 (10)

O1—C4	1.366 (2)	C18—C19	1.392 (3)
O1—C29	1.416 (3)	C18—H18	0.9500
O2—C5	1.373 (2)	C19—C20	1.374 (4)
O2—C30	1.412 (3)	C19—H19	0.9500
O3—C10	1.441 (2)	C20—C21	1.370 (4)
O3—H3O	0.91 (3)	C20—H20	0.9500
N1—C9	1.476 (2)	C21—C22	1.373 (3)
N1—C31	1.477 (2)	C21—H21	0.9500
N1—C1	1.479 (2)	C22—H22	0.9500
C1—C2	1.522 (2)	C23—C28	1.385 (3)
C1—C23	1.530 (2)	C23—C24	1.387 (3)
C1—H1	1.0000	C24—C25	1.386 (3)
C2—C7	1.388 (3)	C24—H24	0.9500
C2—C3	1.403 (2)	C25—C26	1.378 (3)
C3—C4	1.373 (3)	C25—H25	0.9500
C3—H3	0.9500	C26—C27	1.382 (4)
C4—C5	1.408 (3)	C26—H26	0.9500
C5—C6	1.373 (3)	C27—C28	1.384 (3)
C6—C7	1.402 (3)	C27—H27	0.9500
C6—H6	0.9500	C28—H28	0.9500
C7—C8	1.509 (2)	C29—H29A	0.9800
C8—C9	1.526 (2)	C29—H29B	0.9800
C8—H8A	0.9900	C29—H29C	0.9800
C8—H8B	0.9900	C30—H30A	0.9800
C9—C10	1.560 (2)	C30—H30B	0.9800
C9—H9	1.0000	C30—H30C	0.9800
C10—C17	1.527 (3)	C31—C32	1.506 (3)
C10—C11	1.539 (3)	C31—H31A	0.9900
C11—C12	1.387 (3)	C31—H31B	0.9900
C11—C16	1.397 (3)	C32—C33	1.382 (3)
C12—C13	1.390 (3)	C32—C37	1.391 (3)
C12—H12	0.9500	C33—C34	1.410 (4)
C13—C14	1.376 (3)	C33—H33	0.9500
C13—H13	0.9500	C34—C35	1.365 (5)
C14—C15	1.375 (3)	C34—H34	0.9500
C14—H14	0.9500	C35—C36	1.360 (4)
C15—C16	1.379 (3)	C35—H35	0.9500
C15—H15	0.9500	C36—C37	1.373 (3)
C16—H16	0.9500	C36—H36	0.9500
C17—C18	1.382 (3)	C37—H37	0.9500
C17—C22	1.389 (3)
C4—O1—C29	117.08 (15)	C17—C18—C19	120.6 (2)
C5—O2—C30	117.80 (15)	C17—C18—H18	119.7
C10—O3—H3O	108 (2)	C19—C18—H18	119.7
C9—N1—C31	114.74 (13)	C20—C19—C18	120.3 (2)
C9—N1—C1	109.60 (14)	C20—C19—H19	119.8
C31—N1—C1	110.47 (14)	C18—C19—H19	119.8
N1—C1—C2	112.41 (14)	C21—C20—C19	119.6 (2)
N1—C1—C23	109.51 (13)	C21—C20—H20	120.2
C2—C1—C23	115.48 (15)	C19—C20—H20	120.2
N1—C1—H1	106.3	C20—C21—C22	120.2 (2)
C2—C1—H1	106.3	C20—C21—H21	119.9
C23—C1—H1	106.3	C22—C21—H21	119.9
C7—C2—C3	119.34 (16)	C21—C22—C17	121.5 (2)
C7—C2—C1	121.35 (15)	C21—C22—H22	119.2
C3—C2—C1	119.28 (16)	C17—C22—H22	119.2
C4—C3—C2	121.52 (17)	C28—C23—C24	118.13 (18)
C4—C3—H3	119.2	C28—C23—C1	118.02 (17)
C2—C3—H3	119.2	C24—C23—C1	123.85 (17)
O1—C4—C3	125.99 (17)	C25—C24—C23	120.6 (2)
O1—C4—C5	114.97 (16)	C25—C24—H24	119.7
C3—C4—C5	119.04 (16)	C23—C24—H24	119.7
C6—C5—O2	125.18 (17)	C26—C25—C24	120.5 (2)
C6—C5—C4	119.63 (16)	C26—C25—H25	119.7
O2—C5—C4	115.18 (16)	C24—C25—H25	119.7
C5—C6—C7	121.47 (17)	C25—C26—C27	119.6 (2)
C5—C6—H6	119.3	C25—C26—H26	120.2
C7—C6—H6	119.3	C27—C26—H26	120.2
C2—C7—C6	118.96 (16)	C26—C27—C28	119.6 (2)
C2—C7—C8	121.43 (16)	C26—C27—H27	120.2
C6—C7—C8	119.58 (15)	C28—C27—H27	120.2
C7—C8—C9	110.96 (14)	C27—C28—C23	121.6 (2)
C7—C8—H8A	109.4	C27—C28—H28	119.2
C9—C8—H8A	109.4	C23—C28—H28	119.2
C7—C8—H8B	109.4	O1—C29—H29A	109.5
C9—C8—H8B	109.4	O1—C29—H29B	109.5
H8A—C8—H8B	108.0	H29A—C29—H29B	109.5
N1—C9—C8	111.20 (14)	O1—C29—H29C	109.5
N1—C9—C10	112.43 (15)	H29A—C29—H29C	109.5
C8—C9—C10	114.31 (14)	H29B—C29—H29C	109.5
N1—C9—H9	106.1	O2—C30—H30A	109.5
C8—C9—H9	106.1	O2—C30—H30B	109.5
C10—C9—H9	106.1	H30A—C30—H30B	109.5
O3—C10—C17	107.77 (15)	O2—C30—H30C	109.5
O3—C10—C11	108.05 (14)	H30A—C30—H30C	109.5
C17—C10—C11	107.71 (14)	H30B—C30—H30C	109.5
O3—C10—C9	110.11 (14)	N1—C31—C32	110.84 (14)
C17—C10—C9	109.74 (14)	N1—C31—H31A	109.5
C11—C10—C9	113.28 (15)	C32—C31—H31A	109.5
C12—C11—C16	117.22 (18)	N1—C31—H31B	109.5
C12—C11—C10	125.39 (15)	C32—C31—H31B	109.5
C16—C11—C10	117.37 (17)	H31A—C31—H31B	108.1
C11—C12—C13	121.01 (16)	C33—C32—C37	118.8 (2)
C11—C12—H12	119.5	C33—C32—C31	121.4 (2)
C13—C12—H12	119.5	C37—C32—C31	119.80 (19)
C14—C13—C12	120.46 (19)	C32—C33—C34	119.6 (3)
C14—C13—H13	119.8	C32—C33—H33	120.2
C12—C13—H13	119.8	C34—C33—H33	120.2
C13—C14—C15	119.53 (19)	C35—C34—C33	119.9 (3)
C13—C14—H14	120.2	C35—C34—H34	120.1
C15—C14—H14	120.2	C33—C34—H34	120.1
C14—C15—C16	119.97 (17)	C36—C35—C34	120.6 (3)
C14—C15—H15	120.0	C36—C35—H35	119.7
C16—C15—H15	120.0	C34—C35—H35	119.7
C15—C16—C11	121.8 (2)	C35—C36—C37	120.4 (3)
C15—C16—H16	119.1	C35—C36—H36	119.8
C11—C16—H16	119.1	C37—C36—H36	119.8
C18—C17—C22	117.82 (18)	C36—C37—C32	120.8 (3)
C18—C17—C10	122.22 (17)	C36—C37—H37	119.6
C22—C17—C10	119.94 (17)	C32—C37—H37	119.6
C9—N1—C1—C2	−49.61 (18)	C16—C11—C12—C13	−1.6 (3)
C31—N1—C1—C2	77.77 (18)	C10—C11—C12—C13	179.67 (18)
C9—N1—C1—C23	80.17 (17)	C11—C12—C13—C14	0.6 (3)
C31—N1—C1—C23	−152.45 (15)	C12—C13—C14—C15	0.7 (3)
N1—C1—C2—C7	17.4 (2)	C13—C14—C15—C16	−0.8 (3)
C23—C1—C2—C7	−109.28 (19)	C14—C15—C16—C11	−0.2 (3)
N1—C1—C2—C3	−160.34 (16)	C12—C11—C16—C15	1.4 (3)
C23—C1—C2—C3	73.0 (2)	C10—C11—C16—C15	−179.74 (17)
C7—C2—C3—C4	−0.9 (3)	O3—C10—C17—C18	−7.7 (2)
C1—C2—C3—C4	176.84 (17)	C11—C10—C17—C18	108.7 (2)
C29—O1—C4—C3	−7.4 (3)	C9—C10—C17—C18	−127.62 (19)
C29—O1—C4—C5	172.86 (19)	O3—C10—C17—C22	174.30 (16)
C2—C3—C4—O1	−177.54 (18)	C11—C10—C17—C22	−69.3 (2)
C2—C3—C4—C5	2.2 (3)	C9—C10—C17—C22	54.4 (2)
C30—O2—C5—C6	11.0 (3)	C22—C17—C18—C19	1.2 (3)
C30—O2—C5—C4	−169.7 (2)	C10—C17—C18—C19	−176.8 (2)
O1—C4—C5—C6	178.01 (18)	C17—C18—C19—C20	−0.6 (4)
C3—C4—C5—C6	−1.8 (3)	C18—C19—C20—C21	0.0 (4)
O1—C4—C5—O2	−1.3 (3)	C19—C20—C21—C22	−0.1 (4)
C3—C4—C5—O2	178.95 (18)	C20—C21—C22—C17	0.7 (3)
O2—C5—C6—C7	179.27 (19)	C18—C17—C22—C21	−1.3 (3)
C4—C5—C6—C7	0.0 (3)	C10—C17—C22—C21	176.81 (19)
C3—C2—C7—C6	−0.8 (3)	N1—C1—C23—C28	61.0 (2)
C1—C2—C7—C6	−178.51 (17)	C2—C1—C23—C28	−170.93 (16)
C3—C2—C7—C8	177.34 (17)	N1—C1—C23—C24	−118.47 (18)
C1—C2—C7—C8	−0.4 (3)	C2—C1—C23—C24	9.6 (2)
C5—C6—C7—C2	1.2 (3)	C28—C23—C24—C25	−1.6 (3)
C5—C6—C7—C8	−176.95 (18)	C1—C23—C24—C25	177.84 (18)
C2—C7—C8—C9	15.5 (2)	C23—C24—C25—C26	1.0 (3)
C6—C7—C8—C9	−166.40 (17)	C24—C25—C26—C27	0.9 (4)
C31—N1—C9—C8	−57.74 (19)	C25—C26—C27—C28	−2.0 (4)
C1—N1—C9—C8	67.21 (17)	C26—C27—C28—C23	1.4 (4)
C31—N1—C9—C10	71.89 (18)	C24—C23—C28—C27	0.4 (3)
C1—N1—C9—C10	−163.16 (14)	C1—C23—C28—C27	−179.1 (2)
C7—C8—C9—N1	−48.4 (2)	C9—N1—C31—C32	−162.95 (15)
C7—C8—C9—C10	−177.03 (16)	C1—N1—C31—C32	72.56 (19)
N1—C9—C10—O3	−77.04 (18)	N1—C31—C32—C33	−122.4 (2)
C8—C9—C10—O3	51.0 (2)	N1—C31—C32—C37	57.8 (2)
N1—C9—C10—C17	41.44 (19)	C37—C32—C33—C34	0.8 (3)
C8—C9—C10—C17	169.44 (15)	C31—C32—C33—C34	−178.93 (19)
N1—C9—C10—C11	161.84 (14)	C32—C33—C34—C35	0.5 (4)
C8—C9—C10—C11	−70.15 (19)	C33—C34—C35—C36	−1.2 (4)
O3—C10—C11—C12	−127.94 (18)	C34—C35—C36—C37	0.5 (4)
C17—C10—C11—C12	115.89 (18)	C35—C36—C37—C32	0.9 (3)
C9—C10—C11—C12	−5.7 (2)	C33—C32—C37—C36	−1.6 (3)
O3—C10—C11—C16	53.3 (2)	C31—C32—C37—C36	178.20 (18)
C17—C10—C11—C16	−62.88 (19)	O3—C10—C9—N1	−77.04 (18)
C9—C10—C11—C16	175.57 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O2i	0.95	2.44	3.385 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O2i	0.95	2.44	3.385 (2)	171

Symmetry code: (i) .