(1R,3S)-N-Benzhydryl-2-benzyl-6,7-dimeth-oxy-1-phenyl-1,2,3,4-tetra-hydro-isoquinoline-3-carbothio-amide.

The title compound, C(38)H(36)N(2)O(2)S, has a heterocyclic ring that assumes a half-chair conformation. The phenyl rings of neighbouring mol-ecules align forming alternating chains parallel to [100] within the crystal packing. The absolute stereochemistry of the crystal was confirmed to be R,S at the 1- and 3-positions, respectively, by proton NMR spectroscopy. A single intra-molecular N-H⋯N hydrogen bond is observed.

Related literature

For background to chiral organocatalysts bearing a tetra­hydro­isoquinoline framework and for related structures, see: Naicker et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C38H36N2O2S

M = 584.75

Orthorhombic,

a = 9.0463 (1) Å

b = 17.6687 (2) Å

c = 19.6178 (2) Å

V = 3135.64 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 173 K

0.34 × 0.32 × 0.30 mm

Data collection

Nonius KappaCCD diffractometer

7464 measured reflections

7464 independent reflections

6545 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.090

S = 1.06

7464 reflections

394 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 3271 Friedel pairs

Flack parameter: −0.07 (5)

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomov et al., 2009) ▶; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811049324/hg5134sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049324/hg5134Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049324/hg5134Isup3.cml

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

C38H36N2O2S	Dx = 1.239 Mg m−3
Mr = 584.75	Melting point: 458 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7464 reflections
a = 9.0463 (1) Å	θ = 2.4–27.9°
b = 17.6687 (2) Å	µ = 0.14 mm−1
c = 19.6178 (2) Å	T = 173 K
V = 3135.64 (6) Å3	Block, colourless
Z = 4	0.34 × 0.32 × 0.30 mm
F(000) = 1240

Nonius KappaCCD diffractometer	6545 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.013
graphite	θmax = 27.9°, θmin = 2.4°
1.2° φ scans and ω scans	h = −11→11
7464 measured reflections	k = −23→23
7464 independent reflections	l = −25→25

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0573P)2 + 0.1291P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
7464 reflections	Δρmax = 0.19 e Å−3
394 parameters	Δρmin = −0.25 e Å−3
0 restraints	Absolute structure: Flack (1983), 3271 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.07 (5)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
S1	0.56498 (4)	0.31046 (3)	0.215098 (18)	0.04475 (11)
O1	1.39454 (9)	0.35968 (6)	−0.01266 (5)	0.0361 (2)
O2	1.15098 (11)	0.39105 (6)	−0.07511 (5)	0.0412 (3)
N1	0.98038 (11)	0.23680 (6)	0.21258 (5)	0.0254 (2)
H1N	0.8629 (19)	0.2485 (9)	0.3066 (8)	0.038 (4)*
N2	0.76795 (13)	0.26373 (7)	0.30274 (5)	0.0300 (2)
C1	1.12804 (13)	0.26381 (7)	0.19152 (6)	0.0258 (2)
H1	1.1954	0.2189	0.1909	0.031*
C2	1.12788 (13)	0.29751 (7)	0.11981 (6)	0.0252 (2)
C3	1.26341 (13)	0.31006 (7)	0.08659 (6)	0.0258 (2)
H3	1.3530	0.2963	0.1087	0.031*
C4	1.26841 (14)	0.34205 (7)	0.02236 (6)	0.0277 (3)
C5	1.13534 (14)	0.36025 (8)	−0.01141 (6)	0.0295 (3)
C6	1.00254 (14)	0.34772 (7)	0.02100 (6)	0.0296 (3)
H6	0.9130	0.3605	−0.0015	0.036*
C7	0.99719 (13)	0.31627 (7)	0.08690 (6)	0.0263 (2)
C8	0.84760 (13)	0.30508 (8)	0.12010 (6)	0.0281 (3)
H8A	0.7988	0.2595	0.1012	0.034*
H8B	0.7836	0.3494	0.1111	0.034*
C9	0.87122 (13)	0.29575 (7)	0.19647 (6)	0.0254 (3)
H9	0.9174	0.3443	0.2118	0.030*
C10	0.73303 (14)	0.28667 (7)	0.24034 (6)	0.0273 (3)
C11	0.66652 (15)	0.25452 (8)	0.36016 (6)	0.0307 (3)
H11	0.5659	0.2705	0.3447	0.037*
C12	0.66026 (16)	0.17078 (8)	0.37684 (7)	0.0365 (3)
C13	0.57712 (19)	0.12406 (10)	0.33433 (10)	0.0513 (4)
H13	0.5187	0.1457	0.2991	0.062*
C14	0.5791 (2)	0.04658 (12)	0.34297 (13)	0.0717 (6)
H14	0.5222	0.0151	0.3138	0.086*
C15	0.6627 (3)	0.01513 (11)	0.39351 (13)	0.0783 (7)
H15	0.6639	−0.0383	0.3991	0.094*
C16	0.7452 (3)	0.05997 (12)	0.43635 (10)	0.0724 (7)
H16	0.8025	0.0375	0.4715	0.087*
C17	0.7449 (2)	0.13879 (10)	0.42834 (8)	0.0519 (4)
H17	0.8020	0.1699	0.4578	0.062*
C18	0.71133 (15)	0.30534 (8)	0.41918 (7)	0.0355 (3)
C19	0.62417 (18)	0.30449 (10)	0.47767 (7)	0.0461 (4)
H19	0.5398	0.2725	0.4797	0.055*
C20	0.6594 (2)	0.34981 (12)	0.53304 (9)	0.0596 (5)
H20	0.5989	0.3490	0.5726	0.071*
C21	0.7820 (2)	0.39607 (13)	0.53074 (10)	0.0679 (6)
H21	0.8059	0.4270	0.5688	0.081*
C22	0.8697 (2)	0.39761 (14)	0.47359 (11)	0.0721 (6)
H22	0.9541	0.4296	0.4720	0.087*
C23	0.8343 (2)	0.35184 (11)	0.41767 (9)	0.0533 (4)
H23	0.8953	0.3527	0.3783	0.064*
C24	1.18222 (13)	0.31673 (8)	0.24787 (6)	0.0274 (3)
C25	1.21466 (16)	0.28510 (9)	0.31128 (7)	0.0377 (3)
H25	1.2090	0.2318	0.3171	0.045*
C26	1.25474 (18)	0.32987 (11)	0.36556 (7)	0.0494 (4)
H26	1.2770	0.3073	0.4083	0.059*
C27	1.2627 (2)	0.40751 (11)	0.35813 (8)	0.0525 (4)
H27	1.2896	0.4384	0.3957	0.063*
C28	1.23137 (18)	0.43995 (10)	0.29567 (8)	0.0461 (4)
H28	1.2370	0.4933	0.2902	0.055*
C29	1.19146 (15)	0.39432 (8)	0.24068 (7)	0.0347 (3)
H29	1.1704	0.4169	0.1978	0.042*
C30	0.94220 (15)	0.16198 (7)	0.18354 (6)	0.0311 (3)
H30A	0.9619	0.1621	0.1339	0.037*
H30B	0.8356	0.1519	0.1905	0.037*
C31	1.03199 (15)	0.10040 (7)	0.21717 (7)	0.0313 (3)
C32	1.00795 (17)	0.08224 (8)	0.28514 (7)	0.0369 (3)
H32	0.9328	0.1078	0.3099	0.044*
C33	1.09188 (18)	0.02740 (9)	0.31743 (9)	0.0449 (4)
H33	1.0739	0.0154	0.3639	0.054*
C34	1.20184 (17)	−0.00989 (8)	0.28199 (10)	0.0483 (4)
H34	1.2612	−0.0466	0.3044	0.058*
C35	1.22548 (19)	0.00598 (9)	0.21423 (10)	0.0535 (4)
H35	1.2999	−0.0203	0.1896	0.064*
C36	1.13978 (18)	0.06090 (9)	0.18180 (9)	0.0442 (4)
H36	1.1556	0.0713	0.1349	0.053*
C37	1.53137 (14)	0.34969 (9)	0.02154 (7)	0.0368 (3)
H37A	1.5315	0.3794	0.0637	0.055*
H37B	1.6122	0.3667	−0.0080	0.055*
H37C	1.5449	0.2960	0.0325	0.055*
C38	1.01921 (18)	0.40522 (12)	−0.11254 (8)	0.0523 (4)
H38A	0.9625	0.3582	−0.1168	0.078*
H38B	1.0446	0.4240	−0.1580	0.078*
H38C	0.9597	0.4432	−0.0886	0.078*

	U11	U22	U33	U12	U13	U23
S1	0.02261 (15)	0.0813 (3)	0.03029 (17)	0.00153 (17)	−0.00103 (14)	0.01267 (18)
O1	0.0218 (4)	0.0640 (6)	0.0226 (4)	−0.0016 (4)	0.0025 (3)	0.0056 (5)
O2	0.0294 (5)	0.0712 (7)	0.0230 (5)	−0.0013 (5)	−0.0009 (4)	0.0162 (5)
N1	0.0222 (5)	0.0317 (5)	0.0222 (5)	0.0003 (4)	0.0004 (4)	0.0019 (4)
N2	0.0229 (5)	0.0445 (6)	0.0227 (5)	0.0020 (5)	0.0021 (4)	0.0030 (4)
C1	0.0216 (6)	0.0343 (6)	0.0215 (6)	0.0009 (5)	−0.0017 (5)	0.0020 (5)
C2	0.0250 (6)	0.0323 (6)	0.0183 (5)	0.0005 (5)	0.0010 (5)	−0.0018 (5)
C3	0.0208 (5)	0.0355 (6)	0.0212 (5)	0.0016 (5)	−0.0012 (5)	−0.0014 (5)
C4	0.0243 (6)	0.0380 (6)	0.0208 (6)	−0.0013 (5)	0.0024 (5)	−0.0020 (5)
C5	0.0281 (6)	0.0423 (7)	0.0180 (5)	−0.0022 (5)	−0.0009 (5)	0.0035 (5)
C6	0.0243 (6)	0.0422 (7)	0.0224 (6)	0.0009 (5)	−0.0038 (5)	0.0040 (5)
C7	0.0231 (6)	0.0353 (6)	0.0204 (5)	−0.0001 (5)	0.0004 (5)	0.0007 (5)
C8	0.0219 (6)	0.0407 (7)	0.0216 (6)	0.0018 (5)	−0.0007 (5)	0.0039 (5)
C9	0.0200 (5)	0.0355 (6)	0.0207 (6)	−0.0001 (5)	−0.0004 (4)	0.0021 (5)
C10	0.0238 (6)	0.0351 (6)	0.0230 (6)	−0.0022 (5)	0.0002 (5)	0.0013 (5)
C11	0.0255 (6)	0.0458 (8)	0.0206 (6)	0.0015 (6)	0.0038 (5)	0.0012 (5)
C12	0.0341 (7)	0.0478 (8)	0.0275 (6)	0.0034 (6)	0.0126 (6)	0.0038 (6)
C13	0.0409 (9)	0.0509 (9)	0.0622 (11)	−0.0062 (7)	0.0103 (8)	−0.0039 (8)
C14	0.0596 (12)	0.0533 (11)	0.1023 (18)	−0.0122 (9)	0.0277 (13)	−0.0074 (12)
C15	0.1006 (17)	0.0443 (10)	0.0899 (16)	0.0067 (11)	0.0567 (15)	0.0114 (11)
C16	0.1033 (17)	0.0658 (12)	0.0480 (10)	0.0370 (13)	0.0324 (12)	0.0247 (10)
C17	0.0691 (11)	0.0576 (9)	0.0289 (7)	0.0223 (9)	0.0124 (7)	0.0087 (7)
C18	0.0349 (7)	0.0471 (8)	0.0244 (6)	0.0062 (6)	−0.0002 (5)	−0.0011 (6)
C19	0.0486 (9)	0.0604 (9)	0.0294 (7)	0.0029 (8)	0.0071 (7)	−0.0055 (7)
C20	0.0639 (11)	0.0822 (13)	0.0326 (8)	0.0110 (10)	0.0034 (8)	−0.0154 (8)
C21	0.0647 (12)	0.0924 (14)	0.0466 (10)	0.0085 (11)	−0.0098 (9)	−0.0324 (10)
C22	0.0525 (11)	0.0978 (15)	0.0660 (13)	−0.0125 (10)	−0.0053 (10)	−0.0334 (12)
C23	0.0420 (9)	0.0742 (11)	0.0438 (9)	−0.0045 (8)	0.0056 (7)	−0.0170 (8)
C24	0.0192 (5)	0.0433 (7)	0.0198 (6)	0.0003 (5)	0.0000 (4)	−0.0005 (5)
C25	0.0329 (7)	0.0549 (8)	0.0254 (6)	−0.0070 (6)	−0.0057 (6)	0.0076 (6)
C26	0.0445 (9)	0.0813 (12)	0.0225 (6)	−0.0125 (8)	−0.0070 (6)	0.0035 (7)
C27	0.0495 (9)	0.0759 (12)	0.0322 (8)	−0.0116 (9)	−0.0053 (7)	−0.0157 (8)
C28	0.0455 (8)	0.0502 (8)	0.0427 (9)	−0.0019 (7)	−0.0066 (7)	−0.0112 (7)
C29	0.0319 (7)	0.0438 (7)	0.0284 (7)	0.0000 (6)	−0.0050 (5)	−0.0002 (6)
C30	0.0314 (6)	0.0367 (7)	0.0252 (6)	−0.0026 (5)	−0.0017 (5)	−0.0004 (5)
C31	0.0324 (7)	0.0307 (6)	0.0307 (6)	−0.0050 (5)	−0.0009 (5)	−0.0019 (5)
C32	0.0453 (8)	0.0353 (7)	0.0300 (7)	0.0008 (6)	−0.0027 (6)	−0.0012 (6)
C33	0.0562 (10)	0.0364 (7)	0.0421 (8)	−0.0038 (7)	−0.0116 (8)	0.0052 (6)
C34	0.0419 (8)	0.0338 (7)	0.0693 (11)	−0.0036 (6)	−0.0122 (8)	0.0103 (7)
C35	0.0433 (9)	0.0411 (8)	0.0762 (12)	0.0069 (7)	0.0152 (9)	0.0040 (8)
C36	0.0484 (9)	0.0402 (7)	0.0439 (8)	0.0014 (7)	0.0117 (7)	0.0035 (7)
C37	0.0231 (6)	0.0587 (9)	0.0285 (6)	0.0000 (6)	0.0012 (5)	0.0009 (6)
C38	0.0369 (8)	0.0890 (12)	0.0310 (7)	−0.0062 (8)	−0.0069 (6)	0.0259 (8)

S1—C10	1.6532 (13)	C18—C23	1.383 (2)
O1—C4	1.3679 (15)	C18—C19	1.392 (2)
O1—C37	1.4190 (15)	C19—C20	1.387 (2)
O2—C5	1.3704 (15)	C19—H19	0.9500
O2—C38	1.4223 (17)	C20—C21	1.379 (3)
N1—C9	1.4696 (16)	C20—H20	0.9500
N1—C1	1.4773 (15)	C21—C22	1.374 (3)
N1—C30	1.4804 (16)	C21—H21	0.9500
N2—C10	1.3276 (16)	C22—C23	1.400 (3)
N2—C11	1.4621 (16)	C22—H22	0.9500
N2—H1N	0.903 (17)	C23—H23	0.9500
C1—C2	1.5277 (16)	C24—C29	1.381 (2)
C1—C24	1.5286 (17)	C24—C25	1.3950 (18)
C1—H1	1.0000	C25—C26	1.375 (2)
C2—C7	1.3872 (16)	C25—H25	0.9500
C2—C3	1.4061 (17)	C26—C27	1.381 (3)
C3—C4	1.3817 (17)	C26—H26	0.9500
C3—H3	0.9500	C27—C28	1.382 (2)
C4—C5	1.4111 (18)	C27—H27	0.9500
C5—C6	1.3771 (18)	C28—C29	1.394 (2)
C6—C7	1.4080 (17)	C28—H28	0.9500
C6—H6	0.9500	C29—H29	0.9500
C7—C8	1.5148 (17)	C30—C31	1.5096 (19)
C8—C9	1.5223 (16)	C30—H30A	0.9900
C8—H8A	0.9900	C30—H30B	0.9900
C8—H8B	0.9900	C31—C36	1.385 (2)
C9—C10	1.5262 (17)	C31—C32	1.389 (2)
C9—H9	1.0000	C32—C33	1.384 (2)
C11—C12	1.516 (2)	C32—H32	0.9500
C11—C18	1.5202 (19)	C33—C34	1.381 (2)
C11—H11	1.0000	C33—H33	0.9500
C12—C17	1.388 (2)	C34—C35	1.375 (3)
C12—C13	1.394 (2)	C34—H34	0.9500
C13—C14	1.379 (3)	C35—C36	1.396 (2)
C13—H13	0.9500	C35—H35	0.9500
C14—C15	1.365 (4)	C36—H36	0.9500
C14—H14	0.9500	C37—H37A	0.9800
C15—C16	1.375 (4)	C37—H37B	0.9800
C15—H15	0.9500	C37—H37C	0.9800
C16—C17	1.401 (3)	C38—H38A	0.9800
C16—H16	0.9500	C38—H38B	0.9800
C17—H17	0.9500	C38—H38C	0.9800
C4—O1—C37	117.50 (10)	C23—C18—C11	123.29 (13)
C5—O2—C38	117.01 (11)	C19—C18—C11	118.05 (13)
C9—N1—C1	108.58 (9)	C20—C19—C18	120.62 (16)
C9—N1—C30	113.17 (10)	C20—C19—H19	119.7
C1—N1—C30	113.06 (10)	C18—C19—H19	119.7
C10—N2—C11	126.52 (11)	C21—C20—C19	120.09 (17)
C10—N2—H1N	113.2 (10)	C21—C20—H20	120.0
C11—N2—H1N	120.0 (10)	C19—C20—H20	120.0
N1—C1—C2	112.49 (9)	C22—C21—C20	120.22 (16)
N1—C1—C24	106.58 (10)	C22—C21—H21	119.9
C2—C1—C24	115.33 (10)	C20—C21—H21	119.9
N1—C1—H1	107.4	C21—C22—C23	119.72 (19)
C2—C1—H1	107.4	C21—C22—H22	120.1
C24—C1—H1	107.4	C23—C22—H22	120.1
C7—C2—C3	119.32 (10)	C18—C23—C22	120.69 (16)
C7—C2—C1	121.50 (10)	C18—C23—H23	119.7
C3—C2—C1	119.17 (11)	C22—C23—H23	119.7
C4—C3—C2	121.04 (11)	C29—C24—C25	118.44 (12)
C4—C3—H3	119.5	C29—C24—C1	123.56 (11)
C2—C3—H3	119.5	C25—C24—C1	117.86 (12)
O1—C4—C3	125.35 (11)	C26—C25—C24	121.03 (15)
O1—C4—C5	115.08 (10)	C26—C25—H25	119.5
C3—C4—C5	119.57 (11)	C24—C25—H25	119.5
O2—C5—C6	125.09 (12)	C25—C26—C27	120.22 (15)
O2—C5—C4	115.50 (11)	C25—C26—H26	119.9
C6—C5—C4	119.40 (11)	C27—C26—H26	119.9
C5—C6—C7	121.15 (11)	C26—C27—C28	119.65 (14)
C5—C6—H6	119.4	C26—C27—H27	120.2
C7—C6—H6	119.4	C28—C27—H27	120.2
C2—C7—C6	119.50 (11)	C27—C28—C29	119.95 (16)
C2—C7—C8	122.00 (10)	C27—C28—H28	120.0
C6—C7—C8	118.49 (11)	C29—C28—H28	120.0
C7—C8—C9	108.18 (10)	C24—C29—C28	120.71 (13)
C7—C8—H8A	110.1	C24—C29—H29	119.6
C9—C8—H8A	110.1	C28—C29—H29	119.6
C7—C8—H8B	110.1	N1—C30—C31	110.48 (10)
C9—C8—H8B	110.1	N1—C30—H30A	109.6
H8A—C8—H8B	108.4	C31—C30—H30A	109.6
N1—C9—C8	112.50 (10)	N1—C30—H30B	109.6
N1—C9—C10	110.78 (10)	C31—C30—H30B	109.6
C8—C9—C10	116.83 (10)	H30A—C30—H30B	108.1
N1—C9—H9	105.2	C36—C31—C32	118.35 (13)
C8—C9—H9	105.2	C36—C31—C30	121.53 (13)
C10—C9—H9	105.2	C32—C31—C30	120.13 (12)
N2—C10—C9	110.92 (10)	C33—C32—C31	121.00 (14)
N2—C10—S1	124.93 (10)	C33—C32—H32	119.5
C9—C10—S1	123.89 (9)	C31—C32—H32	119.5
N2—C11—C12	107.35 (11)	C34—C33—C32	119.92 (16)
N2—C11—C18	110.72 (11)	C34—C33—H33	120.0
C12—C11—C18	114.96 (11)	C32—C33—H33	120.0
N2—C11—H11	107.9	C35—C34—C33	120.09 (15)
C12—C11—H11	107.9	C35—C34—H34	120.0
C18—C11—H11	107.9	C33—C34—H34	120.0
C17—C12—C13	119.47 (15)	C34—C35—C36	119.74 (16)
C17—C12—C11	122.26 (14)	C34—C35—H35	120.1
C13—C12—C11	117.97 (14)	C36—C35—H35	120.1
C14—C13—C12	120.5 (2)	C31—C36—C35	120.86 (15)
C14—C13—H13	119.8	C31—C36—H36	119.6
C12—C13—H13	119.8	C35—C36—H36	119.6
C15—C14—C13	120.0 (2)	O1—C37—H37A	109.5
C15—C14—H14	120.0	O1—C37—H37B	109.5
C13—C14—H14	120.0	H37A—C37—H37B	109.5
C14—C15—C16	120.67 (18)	O1—C37—H37C	109.5
C14—C15—H15	119.7	H37A—C37—H37C	109.5
C16—C15—H15	119.7	H37B—C37—H37C	109.5
C15—C16—C17	120.2 (2)	O2—C38—H38A	109.5
C15—C16—H16	119.9	O2—C38—H38B	109.5
C17—C16—H16	119.9	H38A—C38—H38B	109.5
C12—C17—C16	119.16 (19)	O2—C38—H38C	109.5
C12—C17—H17	120.4	H38A—C38—H38C	109.5
C16—C17—H17	120.4	H38B—C38—H38C	109.5
C23—C18—C19	118.66 (14)
C9—N1—C1—C2	−47.06 (13)	N2—C11—C12—C13	−76.53 (16)
C30—N1—C1—C2	79.40 (12)	C18—C11—C12—C13	159.81 (13)
C9—N1—C1—C24	80.27 (11)	C17—C12—C13—C14	−0.3 (2)
C30—N1—C1—C24	−153.27 (10)	C11—C12—C13—C14	173.60 (15)
N1—C1—C2—C7	14.37 (17)	C12—C13—C14—C15	0.1 (3)
C24—C1—C2—C7	−108.15 (14)	C13—C14—C15—C16	0.2 (3)
N1—C1—C2—C3	−165.91 (11)	C14—C15—C16—C17	−0.4 (3)
C24—C1—C2—C3	71.57 (14)	C13—C12—C17—C16	0.1 (2)
C7—C2—C3—C4	1.25 (18)	C11—C12—C17—C16	−173.46 (15)
C1—C2—C3—C4	−178.48 (11)	C15—C16—C17—C12	0.2 (3)
C37—O1—C4—C3	−5.03 (19)	N2—C11—C18—C23	−1.5 (2)
C37—O1—C4—C5	173.83 (13)	C12—C11—C18—C23	120.33 (16)
C2—C3—C4—O1	176.79 (12)	N2—C11—C18—C19	178.80 (13)
C2—C3—C4—C5	−2.03 (19)	C12—C11—C18—C19	−59.35 (18)
C38—O2—C5—C6	−5.5 (2)	C23—C18—C19—C20	0.5 (2)
C38—O2—C5—C4	175.76 (14)	C11—C18—C19—C20	−179.80 (15)
O1—C4—C5—O2	1.68 (17)	C18—C19—C20—C21	−0.3 (3)
C3—C4—C5—O2	−179.38 (11)	C19—C20—C21—C22	0.1 (3)
O1—C4—C5—C6	−177.17 (12)	C20—C21—C22—C23	−0.1 (3)
C3—C4—C5—C6	1.76 (19)	C19—C18—C23—C22	−0.5 (3)
O2—C5—C6—C7	−179.48 (13)	C11—C18—C23—C22	179.80 (17)
C4—C5—C6—C7	−0.7 (2)	C21—C22—C23—C18	0.3 (3)
C3—C2—C7—C6	−0.20 (18)	N1—C1—C24—C29	−107.96 (13)
C1—C2—C7—C6	179.52 (11)	C2—C1—C24—C29	17.67 (17)
C3—C2—C7—C8	−179.26 (12)	N1—C1—C24—C25	67.68 (14)
C1—C2—C7—C8	0.47 (19)	C2—C1—C24—C25	−166.70 (11)
C5—C6—C7—C2	0.0 (2)	C29—C24—C25—C26	0.1 (2)
C5—C6—C7—C8	179.06 (12)	C1—C24—C25—C26	−175.77 (13)
C2—C7—C8—C9	17.38 (17)	C24—C25—C26—C27	0.4 (2)
C6—C7—C8—C9	−161.69 (11)	C25—C26—C27—C28	−0.5 (3)
C1—N1—C9—C8	69.61 (13)	C26—C27—C28—C29	0.2 (3)
C30—N1—C9—C8	−56.79 (13)	C25—C24—C29—C28	−0.4 (2)
C1—N1—C9—C10	−157.57 (10)	C1—C24—C29—C28	175.21 (13)
C30—N1—C9—C10	76.03 (12)	C27—C28—C29—C24	0.3 (2)
C7—C8—C9—N1	−52.47 (14)	C9—N1—C30—C31	−164.19 (10)
C7—C8—C9—C10	177.76 (10)	C1—N1—C30—C31	71.84 (13)
C11—N2—C10—C9	174.98 (12)	N1—C30—C31—C36	−111.71 (14)
C11—N2—C10—S1	0.6 (2)	N1—C30—C31—C32	68.10 (15)
N1—C9—C10—N2	36.60 (14)	C36—C31—C32—C33	1.6 (2)
C8—C9—C10—N2	167.18 (11)	C30—C31—C32—C33	−178.21 (13)
N1—C9—C10—S1	−148.92 (10)	C31—C32—C33—C34	0.3 (2)
C8—C9—C10—S1	−18.34 (16)	C32—C33—C34—C35	−1.7 (2)
C10—N2—C11—C12	113.87 (15)	C33—C34—C35—C36	1.2 (3)
C10—N2—C11—C18	−119.91 (14)	C32—C31—C36—C35	−2.1 (2)
N2—C11—C12—C17	97.16 (15)	C30—C31—C36—C35	177.71 (14)
C18—C11—C12—C17	−26.50 (19)	C34—C35—C36—C31	0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···N1	0.903 (17)	2.139 (16)	2.6548 (15)	115.4 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N⋯N1	0.903 (17)	2.139 (16)	2.6548 (15)	115.4 (12)