CrystalCMP: an easy-to-use tool for fast comparison of molecular packing

A new approach is introduced for the comparison of molecular packing and the identification of identical crystal structure motifs. It has been tested on data sets for the solid forms of benzamide, cabergoline and trospium. In this approach, the packing similarity is calculated using a simple formula involving the distances between molecular centres and the relative orientations of molecular entities inside a finite molecular cluster. The approach is independent of the atomic labelling, the unit-cell parameters, the space group setting and the number of molecules in the asymmetric part of the unit cell. Owing to its low sensitivity to volume changes, this approach allows the comparison of various solid forms (such as polymorphs, hydrates, solvates, co-crystals or salts) of identical or similar molecular compounds. The method is also suitable for identifying similar results from direct space methods, which are often used in powder diffraction.

Computing details

Data collection: Xcalibur, (Oxford Diffraction, 2002) for TCL_BE, TCL_AC, TR_SAC1; USER DEFINED DATA COLLECTION for TR_SAC2. Cell refinement: CrysAlis, (Oxford Diffraction, 2002) for TCL_BE, TR_SAC1; CrysAlis PRO, (Agilent, 2011) for TCL_AC; USER DEFINED CELL REFINEMENT for TR_SAC2. Data reduction: CrysAlis, (Oxford Diffraction, 2002) for TCL_BE, TR_SAC1, TR_SAC2; CrysAlis PRO, (Agilent, 2011) for TCL_AC. Program(s) used to solve structure: SIR92 (Altomare et al., 1994) for TCL_BE, TCL_AC, TR_SAC1, TR_SAC2. Program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003) for TCL_BE, TCL_AC, TR_SAC1, TR_SAC2. Molecular graphics: CAMERON (Watkin et al., 1996) for TCL_BE, TCL_AC, TR_SAC1, TR_SAC2. Software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003) for TCL_BE, TCL_AC, TR_SAC1, TR_SAC2.

(TCL_AB)

Crystal data

C25H30NO3·C7H7NO2·Cl·H2O	V = 3005.11 (10) Å^3
Mr = 583.1	Z = 4
Monoclinic, Cc	F(000) = 1232
Hall symbol: C -2yc	Dx = 1.289 Mg m^−3
a = 11.6771 (2) Å	Cu Kα radiation
b = 29.1114 (4) Å	T = 293 K
c = 9.36146 (16) Å	white
β = 109.210 (2)°

Data collection

PANalytical Empyrean diffractometer

2θmin = 4.007°, 2θmax = 79.992°, 2θstep = 0.013°

Refinement

Rp = 0.028	105 restraints
Rwp = 0.037	192 constraints
Rexp = 0.012	H-atom parameters constrained
R(F) = 0.057	Weighting scheme based on measured s.u.'s
5788 data points	(Δ/σ)max = 0.055
Profile function: Pseudo-Voigt	Background function: 30 Legendre polynoms
164 parameters	Preferred orientation correction: none

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

	x	y	z	Uiso*/Ueq
O31	1.01304 (4)	0.95996 (2)	0.98156 (6)	0.070 (2)*
O32	0.9948 (2)	0.90987 (6)	1.15555 (17)	0.070 (2)*
N33	0.44205 (18)	0.9750 (2)	0.8519 (7)	0.070 (2)*
C34	0.7387 (2)	0.9217 (2)	1.0518 (7)	0.070 (2)*
C35	0.94823 (13)	0.93693 (4)	1.05308 (12)	0.070 (2)*
C36	0.56797 (14)	0.96650 (15)	0.9022 (4)	0.070 (2)*
C37	0.64412 (16)	0.9904 (2)	0.8390 (7)	0.070 (2)*
C38	0.6163 (2)	0.9318 (2)	1.0084 (8)	0.070 (2)*
C39	0.81631 (15)	0.94668 (12)	0.9939 (4)	0.070 (2)*
C40	0.76743 (15)	0.9811 (2)	0.8866 (7)	0.070 (2)*
C1	0.29459 (10)	0.72904 (7)	0.12803 (19)	0.070 (2)*
C2	0.17138 (9)	0.71768 (4)	0.14940 (12)	0.070 (2)*
C3	0.11088 (17)	0.67602 (4)	0.05363 (16)	0.070 (2)*
C4	0.0424 (7)	0.68213 (6)	−0.0967 (4)	0.070 (2)*
C5	−0.0030 (10)	0.64427 (8)	−0.1889 (5)	0.070 (2)*
C6	0.0193 (12)	0.60043 (7)	−0.1308 (6)	0.070 (2)*
C7	0.0859 (8)	0.59415 (5)	0.0199 (5)	0.070 (2)*
C8	0.1291 (6)	0.63183 (6)	0.1130 (3)	0.070 (2)*
C9	0.18902 (11)	0.70964 (5)	0.31692 (15)	0.070 (2)*
C10	0.2970 (3)	0.7229 (3)	0.4252 (2)	0.070 (2)*
C11	0.3084 (4)	0.7215 (4)	0.5772 (2)	0.070 (2)*
C12	0.2136 (5)	0.7061 (5)	0.6226 (2)	0.070 (2)*
C13	0.1088 (5)	0.6914 (4)	0.5166 (3)	0.070 (2)*
C14	0.0968 (3)	0.6922 (3)	0.36356 (15)	0.070 (2)*
C15	0.49208 (12)	0.69641 (6)	0.1785 (3)	0.070 (2)*
C16	0.51474 (18)	0.68905 (7)	0.0289 (3)	0.070 (2)*
C17	0.52173 (16)	0.63881 (7)	−0.0124 (2)	0.070 (2)*
C18	0.40977 (16)	0.61070 (8)	−0.0159 (3)	0.070 (2)*
C19	0.4360 (2)	0.59460 (8)	0.1495 (4)	0.070 (2)*
C20	0.56266 (19)	0.61348 (8)	0.2372 (2)	0.070 (2)*
C21	0.5591 (2)	0.66189 (9)	0.2992 (2)	0.070 (2)*
C22	0.74455 (14)	0.63825 (7)	0.1557 (3)	0.070 (2)*
C25	0.64967 (19)	0.56731 (7)	0.0709 (3)	0.070 (2)*
O1	0.36186 (12)	0.69082 (6)	0.1482 (4)	0.070 (2)*
O2	0.32366 (19)	0.76529 (11)	0.0900 (6)	0.070 (2)*
O3	0.099481 (16)	0.757843 (12)	0.10506 (6)	0.070 (2)*
N1	0.62177 (13)	0.61549 (6)	0.1141 (2)	0.070 (2)*
Cl	0.7740 (4)	0.44341 (16)	0.0690 (5)	0.034 (3)*
H1c34	0.771029	0.897254	1.122535	0.0842*
H1c37	0.610784	1.013289	0.762741	0.0842*
H1c38	0.564542	0.914979	1.050948	0.0842*
H1c40	0.819573	0.998293	0.845777	0.0842*
H1c4	0.026074	0.712582	−0.137738	0.0842*
H1c5	−0.049984	0.648734	−0.293407	0.0842*
H1c6	−0.011242	0.574372	−0.194887	0.0842*
H1c7	0.102356	0.563643	0.060385	0.0842*
H1c8	0.171654	0.627333	0.218795	0.0842*
H1c10	0.363812	0.733049	0.394831	0.0842*
H1c11	0.38262	0.731261	0.651732	0.0842*
H1c12	0.221532	0.70576	0.727957	0.0842*
H1c13	0.043055	0.680491	0.54777	0.0842*
H1c14	0.024272	0.680588	0.290058	0.0842*
H1c15	0.520981	0.726366	0.216394	0.0842*
H1c16	0.452489	0.70417	−0.050725	0.0842*
H2c16	0.588147	0.704443	0.031687	0.0842*
H1c17	0.532439	0.639394	−0.109759	0.0842*
H1c18	0.402942	0.584421	−0.080147	0.0842*
H2c18	0.33952	0.630176	−0.045202	0.0842*
H1c19	0.377356	0.607835	0.189096	0.0842*
H2c19	0.437647	0.561644	0.153163	0.0842*
H1c20	0.603753	0.595013	0.323849	0.0842*
H1c21	0.522052	0.660839	0.376769	0.0842*
H2c21	0.640327	0.672457	0.349	0.0842*
H1n33	0.395387	0.960103	0.891544	0.0842*
H2n33	0.411066	0.995258	0.781285	0.0842*
Ow	0.6747 (10)	0.3428 (4)	0.1965 (11)	0.058 (8)*
H1o31	1.096954	0.951554	1.023833	0.0842*
H1o3	0.141792	0.780614	0.135642	0.0842*
C23	0.7960 (2)	0.62223 (10)	0.0360 (4)	0.070 (2)*
C24	0.7473 (3)	0.57350 (10)	−0.0025 (4)	0.070 (2)*
H1c23	0.88286	0.621372	0.077511	0.0842*
H2c23	0.765716	0.641366	−0.051944	0.0842*
H1c24	0.711703	0.570432	−0.11023	0.0842*
H2c24	0.811463	0.551832	0.039994	0.0842*
H1c22	0.734491	0.670995	0.14952	0.0842*
H2c22	0.794876	0.627397	0.252886	0.0842*
H1c25	0.578269	0.554473	−0.001436	0.0842*
H2c25	0.681042	0.548964	0.160526	0.0842*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
?	?	?	?	?	?	?

Geometric parameters (Å, º)

O31—C35	1.3431 (16)	C12—C13	1.367 (8)
O32—C35	1.2220 (18)	C12—H1c12	0.96
N33—C36	1.411 (3)	C13—C14	1.394 (3)
N33—Cl^i	3.384 (8)	C13—H1c13	0.96
N33—H1n33	0.87	C14—H1c14	0.96
N33—H2n33	0.87	C15—C16	1.523 (4)
C34—C38	1.383 (4)	C15—C21	1.522 (3)
C34—C39	1.403 (6)	C15—O1	1.461 (2)
C34—H1c34	0.96	C15—H1c15	0.96
C35—C39	1.483 (2)	C16—C17	1.522 (3)
C36—C37	1.404 (6)	C16—H1c16	0.96
C36—C38	1.400 (8)	C16—H2c16	0.96
C37—C40	1.387 (3)	C17—C18	1.533 (3)
C37—H1c37	0.96	C17—N1	1.522 (2)
C38—H1c38	0.96	C17—H1c17	0.96
C39—C40	1.400 (7)	C18—C19	1.549 (4)
C40—H1c40	0.96	C18—H1c18	0.96
C1—C2	1.5520 (18)	C18—H2c18	0.96
C1—O1	1.339 (2)	C19—C20	1.538 (3)
C1—O2	1.198 (4)	C19—H1c19	0.96
C2—C3	1.5353 (16)	C19—H2c19	0.96
C2—C9	1.5310 (18)	C20—C21	1.530 (3)
C2—O3	1.4195 (11)	C20—N1	1.527 (3)
C3—C4	1.383 (4)	C20—H1c20	0.96
C3—C8	1.389 (2)	C21—H1c21	0.96
C4—C5	1.392 (4)	C21—H2c21	0.96
C4—H1c4	0.96	C22—N1	1.510 (2)
C5—C6	1.378 (4)	C22—C23	1.508 (4)
C5—H1c5	0.96	C22—H1c22	0.96
C6—C7	1.381 (7)	C22—H2c22	0.96
C6—H1c6	0.96	C25—N1	1.524 (3)
C7—C8	1.389 (4)	C25—C24	1.523 (5)
C7—H1c7	0.96	C25—H1c25	0.96
C8—H1c8	0.96	C25—H2c25	0.96
C9—C10	1.388 (4)	O3—H1o3	0.82
C9—C14	1.385 (4)	C23—C24	1.527 (4)
C10—C11	1.386 (3)	C23—H1c23	0.96
C10—H1c10	0.96	C23—H2c23	0.96
C11—C12	1.383 (9)	C24—H1c24	0.96
C11—H1c11	0.96	C24—H2c24	0.96
C36—N33—Cl^i	119.9 (4)	C16—C15—O1	106.9 (2)
C36—N33—H1n33	120	C16—C15—H1c15	108.74
C36—N33—H2n33	120	C21—C15—O1	108.6 (2)
Cl^i—N33—H1n33	16.16	C21—C15—H1c15	107.05
Cl^i—N33—H2n33	117.52	O1—C15—H1c15	112.94
H1n33—N33—H2n33	120	C15—C16—C17	114.14 (19)
C38—C34—C39	120.8 (5)	C15—C16—H1c16	109.47
C38—C34—H1c34	119.58	C15—C16—H2c16	109.47
C39—C34—H1c34	119.58	C17—C16—H1c16	109.47
O31—C35—O32	122.34 (17)	C17—C16—H2c16	109.47
O31—C35—C39	113.87 (16)	H1c16—C16—H2c16	104.36
O32—C35—C39	123.8 (2)	C16—C17—C18	113.68 (18)
N33—C36—C37	120.5 (4)	C16—C17—N1	108.82 (15)
N33—C36—C38	119.8 (4)	C16—C17—H1c17	105.01
C37—C36—C38	119.6 (3)	C18—C17—N1	102.08 (16)
C36—C37—C40	120.1 (5)	C18—C17—H1c17	111.44
C36—C37—H1c37	119.94	N1—C17—H1c17	116.09
C40—C37—H1c37	119.94	C17—C18—C19	104.68 (16)
C34—C38—C36	119.9 (5)	C17—C18—H1c18	109.47
C34—C38—H1c38	120.05	C17—C18—H2c18	109.47
C36—C38—H1c38	120.05	C19—C18—H1c18	109.47
C34—C39—C35	118.7 (3)	C19—C18—H2c18	109.47
C34—C39—C40	119.1 (2)	H1c18—C18—H2c18	113.87
C35—C39—C40	122.2 (3)	C18—C19—C20	105.3 (2)
C37—C40—C39	120.4 (5)	C18—C19—H1c19	109.47
C37—C40—H1c40	119.8	C18—C19—H2c19	109.47
C39—C40—H1c40	119.8	C20—C19—H1c19	109.47
C2—C1—O1	109.30 (16)	C20—C19—H2c19	109.47
C2—C1—O2	126.26 (18)	H1c19—C19—H2c19	113.32
O1—C1—O2	124.3 (2)	C19—C20—C21	112.95 (19)
C1—C2—C3	111.17 (13)	C19—C20—N1	101.84 (19)
C1—C2—C9	110.28 (9)	C19—C20—H1c20	112.12
C1—C2—O3	105.72 (10)	C21—C20—N1	109.08 (18)
C3—C2—C9	111.01 (11)	C21—C20—H1c20	105.27
C3—C2—O3	111.45 (8)	N1—C20—H1c20	115.8
C9—C2—O3	107.02 (10)	C15—C21—C20	113.45 (17)
C2—C3—C4	119.59 (13)	C15—C21—H1c21	109.47
C2—C3—C8	121.16 (17)	C15—C21—H2c21	109.47
C4—C3—C8	119.16 (17)	C20—C21—H1c21	109.47
C3—C4—C5	120.3 (2)	C20—C21—H2c21	109.47
C3—C4—H1c4	119.87	H1c21—C21—H2c21	105.17
C5—C4—H1c4	119.87	N1—C22—C23	104.42 (18)
C4—C5—C6	120.3 (4)	N1—C22—H1c22	109.47
C4—C5—H1c5	119.85	N1—C22—H2c22	109.47
C6—C5—H1c5	119.86	C23—C22—H1c22	109.47
C5—C6—C7	119.7 (3)	C23—C22—H2c22	109.47
C5—C6—H1c6	120.15	H1c22—C22—H2c22	114.09
C7—C6—H1c6	120.14	N1—C25—C24	105.54 (18)
C6—C7—C8	120.2 (2)	N1—C25—H1c25	109.47
C6—C7—H1c7	119.9	N1—C25—H2c25	109.47
C8—C7—H1c7	119.9	C24—C25—H1c25	109.47
C3—C8—C7	120.3 (3)	C24—C25—H2c25	109.47
C3—C8—H1c8	119.86	H1c25—C25—H2c25	113.14
C7—C8—H1c8	119.86	C1—O1—C15	117.37 (15)
C2—C9—C10	119.3 (2)	C2—O3—H1o3	109.47
C2—C9—C14	121.50 (11)	C17—N1—C20	100.50 (15)
C10—C9—C14	119.1 (2)	C17—N1—C22	115.18 (16)
C9—C10—C11	119.9 (4)	C17—N1—C25	112.36 (16)
C9—C10—H1c10	120.06	C20—N1—C22	116.68 (17)
C11—C10—H1c10	120.06	C20—N1—C25	110.74 (18)
C10—C11—C12	120.6 (4)	C22—N1—C25	101.80 (15)
C10—C11—H1c11	119.69	C22—C23—C24	104.7 (3)
C12—C11—H1c11	119.69	C22—C23—H1c23	109.47
C11—C12—C13	119.6 (3)	C22—C23—H2c23	109.47
C11—C12—H1c12	120.18	C24—C23—H1c23	109.47
C13—C12—H1c12	120.18	C24—C23—H2c23	109.47
C12—C13—C14	120.3 (5)	H1c23—C23—H2c23	113.82
C12—C13—H1c13	119.87	C25—C24—C23	106.2 (3)
C14—C13—H1c13	119.87	C25—C24—H1c24	109.47
C9—C14—C13	120.3 (4)	C25—C24—H2c24	109.47
C9—C14—H1c14	119.83	C23—C24—H1c24	109.47
C13—C14—H1c14	119.83	C23—C24—H2c24	109.47
C16—C15—C21	112.78 (17)	H1c24—C24—H2c24	112.55

Symmetry code: (i) x−1/2, y+1/2, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
Ow···O32^ii			2.80
O3—H1o3···Ow^iii	0.82	1.90	2.669 (11)	156.16

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

(TCL_BE)

Crystal data

C32H36ClNO5	F(000) = 1168
Mr = 550.09	Dx = 1.261 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 15.64921 (16) Å	Cell parameters from 14134 reflections
b = 19.57407 (17) Å	θ = 5–77°
c = 9.67099 (9) Å	µ = 1.50 mm^−1
β = 102.1287 (10)°	T = 190 K
V = 2896.28 (5) Å^3	Block, colorless
Z = 4	0.60 × 0.40 × 0.30 mm

Data collection

Oxford Diffraction XCALIBUR diffractometer	5390 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.027
ω/2θ scans	θmax = 77.2°, θmin = 4.5°
Absorption correction: multi-scan CrysAlis, (Oxford Diffraction, 2002)	h = −19→19
Tmin = 0.42, Tmax = 0.64	k = −24→24
21898 measured reflections	l = −8→11
5993 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.047	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are: 0.209E + 04 0.354E + 04 0.217E + 04 896. 197.
wR(F^2) = 0.133	(Δ/σ)max = 0.0004271
S = 0.98	Δρmax = 0.45 e Å^−3
5992 reflections	Δρmin = −0.28 e Å^−3
359 parameters	Extinction correction: Larson (1970), Equation 22
54 restraints	Extinction coefficient: 207 (6)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.

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

	x	y	z	Uiso*/Ueq
Cl1	0.48029 (3)	0.61746 (2)	1.25811 (4)	0.0482
O2	0.29949 (8)	0.66198 (6)	1.07730 (15)	0.0484
C3	0.24302 (10)	0.60593 (8)	1.02983 (18)	0.0410
C4	0.29933 (10)	0.55221 (8)	0.97257 (17)	0.0407
O5	0.32511 (8)	0.57769 (6)	0.86051 (13)	0.0498
C6	0.39499 (11)	0.54176 (8)	0.81135 (18)	0.0425
C7	0.48224 (11)	0.56998 (8)	0.88736 (17)	0.0444
C8	0.50606 (13)	0.63713 (9)	0.82535 (16)	0.0477
N9	0.50832 (10)	0.62642 (6)	0.66938 (14)	0.0426
C10	0.56319 (12)	0.56818 (9)	0.63515 (19)	0.0497
C11	0.65571 (14)	0.59571 (12)	0.6686 (2)	0.0646
C12	0.64554 (17)	0.67195 (13)	0.6357 (3)	0.0728
C13	0.54937 (15)	0.68731 (10)	0.6100 (2)	0.0585
C14	0.41085 (12)	0.61987 (9)	0.60711 (17)	0.0477
C15	0.37875 (12)	0.55186 (9)	0.65200 (18)	0.0482
C16	0.37322 (16)	0.68148 (9)	0.6713 (2)	0.0609
C17	0.43549 (16)	0.69243 (9)	0.8162 (2)	0.0616
O18	0.32022 (9)	0.49756 (6)	1.02345 (15)	0.0569
C19	0.17124 (10)	0.63262 (9)	0.91013 (19)	0.0448
C20	0.12515 (13)	0.58921 (11)	0.8084 (2)	0.0590
C21	0.06072 (15)	0.61372 (14)	0.6996 (3)	0.0707
C22	0.04132 (16)	0.68232 (16)	0.6919 (3)	0.0850
C23	0.08564 (18)	0.72557 (14)	0.7927 (3)	0.0924
C24	0.15062 (15)	0.70137 (11)	0.9025 (3)	0.0694
C25	0.20402 (10)	0.57659 (8)	1.15036 (18)	0.0446
C26	0.21030 (13)	0.61291 (11)	1.2742 (2)	0.0562
C27	0.17520 (15)	0.58723 (14)	1.3838 (2)	0.0693
C28	0.13489 (16)	0.52411 (14)	1.3707 (3)	0.0738
C29	0.12724 (16)	0.48819 (12)	1.2471 (3)	0.0716
C30	0.16155 (13)	0.51394 (10)	1.1368 (2)	0.0579
O31	0.64712 (11)	0.65384 (8)	1.16018 (19)	0.0702
C32	0.72209 (16)	0.62787 (12)	1.2282 (3)	0.0674
O33	0.72936 (15)	0.59440 (14)	1.3347 (2)	0.1106
C34	0.79556 (13)	0.64087 (10)	1.1568 (2)	0.0591
C35	0.78618 (16)	0.67684 (13)	1.0325 (3)	0.0707
C36	0.85464 (19)	0.68555 (17)	0.9652 (4)	0.0917
C37	0.93425 (18)	0.65811 (18)	1.0233 (4)	0.0946
C38	0.94717 (16)	0.62286 (15)	1.1470 (5)	0.0939
C39	0.87788 (17)	0.61350 (13)	1.2150 (4)	0.0846
H61	0.3910	0.4928	0.8342	0.0503*
H71	0.4795	0.5793	0.9837	0.0533*
H72	0.5267	0.5363	0.8845	0.0525*
H81	0.5632	0.6533	0.8741	0.0574*
H102	0.5545	0.5268	0.6871	0.0565*
H101	0.5439	0.5598	0.5338	0.0568*
H112	0.6825	0.5884	0.7669	0.0786*
H111	0.6900	0.5726	0.6114	0.0788*
H121	0.6760	0.6992	0.7172	0.0969*
H122	0.6691	0.6833	0.5551	0.0959*
H131	0.5336	0.7294	0.6530	0.0705*
H132	0.5252	0.6889	0.5086	0.0691*
H141	0.4025	0.6226	0.5066	0.0567*
H152	0.3172	0.5473	0.6154	0.0600*
H151	0.4081	0.5156	0.6126	0.0563*
H162	0.3763	0.7211	0.6127	0.0733*
H161	0.3129	0.6710	0.6834	0.0713*
H171	0.4628	0.7364	0.8202	0.0736*
H172	0.4063	0.6876	0.8960	0.0720*
H201	0.1384	0.5424	0.8113	0.0705*
H211	0.0318	0.5848	0.6286	0.0856*
H221	−0.0028	0.6993	0.6169	0.1042*
H231	0.0733	0.7722	0.7878	0.1156*
H241	0.1822	0.7318	0.9733	0.0836*
H261	0.2404	0.6540	1.2848	0.0662*
H271	0.1806	0.6123	1.4671	0.0830*
H281	0.1119	0.5060	1.4450	0.0871*
H291	0.0993	0.4456	1.2370	0.0858*
H301	0.1559	0.4885	1.0519	0.0674*
H351	0.7286	0.6959	0.9943	0.0846*
H361	0.8459	0.7126	0.8775	0.1117*
H371	0.9829	0.6656	0.9789	0.1154*
H381	1.0011	0.6040	1.1867	0.1132*
H21	0.3436 (17)	0.6453 (14)	1.128 (3)	0.0718*
H391	0.8856	0.5900	1.3037	0.1024*
H311	0.607 (2)	0.6414 (17)	1.218 (4)	0.1062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0510 (2)	0.0522 (3)	0.0410 (2)	0.00337 (15)	0.00904 (17)	−0.00341 (14)
O2	0.0417 (6)	0.0377 (6)	0.0646 (8)	−0.0019 (4)	0.0081 (5)	−0.0041 (5)
C3	0.0368 (7)	0.0351 (7)	0.0511 (9)	0.0014 (5)	0.0095 (6)	−0.0005 (6)
C4	0.0372 (7)	0.0364 (7)	0.0489 (8)	0.0016 (6)	0.0099 (6)	0.0007 (6)
O5	0.0563 (7)	0.0423 (6)	0.0553 (7)	0.0165 (5)	0.0220 (6)	0.0083 (5)
C6	0.0468 (8)	0.0336 (7)	0.0493 (8)	0.0085 (6)	0.0148 (7)	0.0013 (6)
C7	0.0524 (9)	0.0444 (8)	0.0359 (7)	0.0038 (7)	0.0081 (6)	0.0077 (6)
C8	0.0676 (11)	0.0438 (8)	0.0309 (8)	−0.0103 (7)	0.0086 (7)	−0.0029 (6)
N9	0.0613 (8)	0.0338 (6)	0.0320 (6)	−0.0009 (5)	0.0085 (6)	0.0009 (5)
C10	0.0562 (9)	0.0457 (8)	0.0497 (9)	0.0041 (7)	0.0170 (7)	0.0051 (7)
C11	0.0629 (10)	0.0671 (10)	0.0655 (10)	−0.0038 (8)	0.0173 (8)	0.0117 (8)
C12	0.0796 (11)	0.0674 (10)	0.0725 (11)	−0.0157 (9)	0.0185 (9)	0.0130 (9)
C13	0.0829 (12)	0.0451 (9)	0.0497 (9)	−0.0094 (8)	0.0192 (8)	0.0059 (7)
C14	0.0589 (10)	0.0480 (9)	0.0337 (8)	0.0125 (7)	0.0039 (7)	0.0016 (6)
C15	0.0490 (9)	0.0497 (9)	0.0441 (8)	0.0036 (7)	0.0060 (7)	−0.0079 (7)
C16	0.0861 (14)	0.0433 (9)	0.0566 (11)	0.0241 (9)	0.0222 (10)	0.0131 (8)
C17	0.1040 (17)	0.0324 (8)	0.0547 (10)	0.0002 (9)	0.0313 (11)	−0.0044 (7)
O18	0.0616 (8)	0.0411 (6)	0.0750 (9)	0.0135 (5)	0.0303 (6)	0.0140 (6)
C19	0.0373 (7)	0.0432 (8)	0.0548 (9)	0.0031 (6)	0.0119 (7)	0.0058 (7)
C20	0.0495 (9)	0.0589 (11)	0.0651 (11)	0.0011 (8)	0.0042 (8)	−0.0030 (9)
C21	0.0523 (11)	0.0918 (15)	0.0641 (12)	−0.0056 (10)	0.0037 (9)	0.0032 (11)
C22	0.0593 (12)	0.0964 (17)	0.0904 (16)	0.0083 (12)	−0.0041 (11)	0.0352 (14)
C23	0.0764 (15)	0.0665 (13)	0.120 (2)	0.0127 (11)	−0.0112 (14)	0.0317 (14)
C24	0.0612 (11)	0.0467 (10)	0.0927 (15)	0.0085 (8)	−0.0011 (10)	0.0106 (10)
C25	0.0378 (7)	0.0450 (8)	0.0510 (9)	0.0049 (6)	0.0094 (6)	0.0019 (7)
C26	0.0511 (10)	0.0640 (11)	0.0526 (10)	−0.0009 (8)	0.0090 (8)	−0.0047 (8)
C27	0.0625 (12)	0.0964 (17)	0.0494 (10)	0.0016 (11)	0.0127 (9)	−0.0026 (11)
C28	0.0703 (13)	0.0908 (17)	0.0669 (13)	0.0095 (12)	0.0292 (11)	0.0219 (12)
C29	0.0742 (14)	0.0596 (12)	0.0920 (16)	−0.0013 (10)	0.0423 (12)	0.0106 (11)
C30	0.0600 (11)	0.0486 (9)	0.0715 (12)	−0.0031 (8)	0.0288 (9)	−0.0016 (8)
O31	0.0642 (9)	0.0618 (9)	0.0882 (11)	0.0026 (7)	0.0242 (8)	0.0076 (8)
C32	0.0711 (13)	0.0578 (11)	0.0686 (13)	−0.0107 (10)	0.0040 (10)	−0.0009 (10)
O33	0.0970 (15)	0.1369 (19)	0.0895 (14)	−0.0217 (14)	0.0003 (11)	0.0403 (14)
C34	0.0500 (10)	0.0449 (9)	0.0778 (13)	−0.0051 (7)	0.0031 (9)	−0.0091 (9)
C35	0.0595 (12)	0.0746 (14)	0.0773 (15)	−0.0048 (10)	0.0131 (10)	−0.0067 (11)
C36	0.0717 (16)	0.111 (2)	0.096 (2)	−0.0171 (15)	0.0261 (14)	−0.0135 (17)
C37	0.0604 (14)	0.102 (2)	0.124 (3)	−0.0170 (14)	0.0253 (15)	−0.040 (2)
C38	0.0474 (12)	0.0813 (18)	0.146 (3)	−0.0014 (11)	0.0035 (15)	−0.0281 (18)
C39	0.0646 (14)	0.0631 (13)	0.113 (2)	−0.0032 (10)	−0.0119 (14)	−0.0028 (13)

Geometric parameters (Å, º)

O2—C3	1.4230 (19)	C17—H171	0.957
O2—H21	0.82 (3)	C17—H172	0.981
C3—C4	1.547 (2)	C19—C20	1.383 (3)
C3—C19	1.526 (2)	C19—C24	1.382 (3)
C3—C25	1.536 (2)	C20—C21	1.382 (3)
C4—O5	1.330 (2)	C20—H201	0.939
C4—O18	1.194 (2)	C21—C22	1.375 (4)
O5—C6	1.4611 (18)	C21—H211	0.931
C6—C7	1.513 (2)	C22—C23	1.365 (4)
C6—C15	1.521 (2)	C22—H221	0.950
C6—H61	0.989	C23—C24	1.390 (3)
C7—C8	1.523 (2)	C23—H231	0.932
C7—H71	0.959	C24—H241	0.963
C7—H72	0.964	C25—C26	1.379 (3)
C8—N9	1.531 (2)	C25—C30	1.388 (3)
C8—C17	1.536 (3)	C26—C27	1.386 (3)
C8—H81	0.972	C26—H261	0.927
N9—C10	1.505 (2)	C27—C28	1.381 (4)
N9—C13	1.522 (2)	C27—H271	0.932
N9—C14	1.523 (2)	C28—C29	1.370 (4)
C10—C11	1.515 (3)	C28—H281	0.938
C10—H102	0.977	C29—C30	1.386 (3)
C10—H101	0.977	C29—H291	0.937
C11—C12	1.527 (3)	C30—H301	0.948
C11—H112	0.966	O31—C32	1.320 (3)
C11—H111	0.961	O31—H311	0.96 (4)
C12—C13	1.503 (3)	C32—O33	1.206 (3)
C12—H121	0.988	C32—C34	1.482 (3)
C12—H122	0.955	C34—C35	1.374 (3)
C13—H131	0.978	C34—C39	1.400 (3)
C13—H132	0.975	C35—C36	1.376 (4)
C14—C15	1.518 (3)	C35—H351	0.973
C14—C16	1.529 (2)	C36—C37	1.365 (4)
C14—H141	0.955	C36—H361	0.984
C15—H152	0.958	C37—C38	1.359 (5)
C15—H151	0.967	C37—H371	0.961
C16—C17	1.544 (3)	C38—C39	1.393 (5)
C16—H162	0.968	C38—H381	0.926
C16—H161	0.997	C39—H391	0.958
C3—O2—H21	105.7 (19)	C14—C16—C17	104.73 (15)
O2—C3—C4	106.12 (12)	C14—C16—H162	108.9
O2—C3—C19	106.80 (13)	C17—C16—H162	108.7
C4—C3—C19	110.18 (13)	C14—C16—H161	109.9
O2—C3—C25	111.24 (14)	C17—C16—H161	110.7
C4—C3—C25	111.37 (13)	H162—C16—H161	113.5
C19—C3—C25	110.92 (13)	C8—C17—C16	105.28 (14)
C3—C4—O5	109.25 (13)	C8—C17—H171	108.7
C3—C4—O18	126.06 (15)	C16—C17—H171	110.7
O5—C4—O18	124.61 (15)	C8—C17—H172	109.6
C4—O5—C6	117.41 (12)	C16—C17—H172	113.1
O5—C6—C7	109.08 (13)	H171—C17—H172	109.3
O5—C6—C15	106.85 (13)	C3—C19—C20	121.35 (15)
C7—C6—C15	112.73 (14)	C3—C19—C24	120.02 (17)
O5—C6—H61	107.9	C20—C19—C24	118.63 (18)
C7—C6—H61	109.8	C19—C20—C21	121.1 (2)
C15—C6—H61	110.3	C19—C20—H201	120.0
C6—C7—C8	113.23 (13)	C21—C20—H201	118.9
C6—C7—H71	108.7	C20—C21—C22	119.8 (2)
C8—C7—H71	106.4	C20—C21—H211	121.0
C6—C7—H72	108.6	C22—C21—H211	119.1
C8—C7—H72	110.0	C21—C22—C23	119.6 (2)
H71—C7—H72	109.8	C21—C22—H221	119.9
C7—C8—N9	109.15 (13)	C23—C22—H221	120.5
C7—C8—C17	113.49 (15)	C22—C23—C24	121.0 (2)
N9—C8—C17	101.82 (14)	C22—C23—H231	120.1
C7—C8—H81	111.5	C24—C23—H231	118.9
N9—C8—H81	108.2	C23—C24—C19	119.8 (2)
C17—C8—H81	112.1	C23—C24—H241	121.1
C8—N9—C10	116.92 (13)	C19—C24—H241	119.1
C8—N9—C13	111.30 (13)	C3—C25—C26	119.95 (16)
C10—N9—C13	101.81 (14)	C3—C25—C30	121.14 (16)
C8—N9—C14	99.94 (13)	C26—C25—C30	118.91 (18)
C10—N9—C14	114.80 (13)	C25—C26—C27	120.6 (2)
C13—N9—C14	112.57 (14)	C25—C26—H261	119.0
N9—C10—C11	104.32 (16)	C27—C26—H261	120.3
N9—C10—H102	111.5	C26—C27—C28	120.1 (2)
C11—C10—H102	114.5	C26—C27—H271	119.5
N9—C10—H101	106.1	C28—C27—H271	120.4
C11—C10—H101	110.7	C27—C28—C29	119.5 (2)
H102—C10—H101	109.2	C27—C28—H281	120.6
C10—C11—C12	104.48 (18)	C29—C28—H281	119.8
C10—C11—H112	110.8	C28—C29—C30	120.5 (2)
C12—C11—H112	110.8	C28—C29—H291	120.0
C10—C11—H111	109.5	C30—C29—H291	119.4
C12—C11—H111	112.7	C25—C30—C29	120.2 (2)
H112—C11—H111	108.5	C25—C30—H301	120.1
C11—C12—C13	106.66 (18)	C29—C30—H301	119.6
C11—C12—H121	110.5	C32—O31—H311	104 (2)
C13—C12—H121	108.8	O31—C32—O33	123.3 (2)
C11—C12—H122	110.9	O31—C32—C34	113.4 (2)
C13—C12—H122	111.3	O33—C32—C34	123.2 (2)
H121—C12—H122	108.8	C32—C34—C35	123.0 (2)
N9—C13—C12	105.57 (16)	C32—C34—C39	119.0 (2)
N9—C13—H131	109.6	C35—C34—C39	117.9 (2)
C12—C13—H131	115.6	C34—C35—C36	121.8 (3)
N9—C13—H132	107.4	C34—C35—H351	116.7
C12—C13—H132	109.7	C36—C35—H351	121.6
H131—C13—H132	108.7	C35—C36—C37	119.4 (3)
N9—C14—C15	108.95 (13)	C35—C36—H361	119.5
N9—C14—C16	102.25 (15)	C37—C36—H361	121.1
C15—C14—C16	113.37 (16)	C36—C37—C38	121.1 (3)
N9—C14—H141	108.0	C36—C37—H371	119.8
C15—C14—H141	111.0	C38—C37—H371	119.0
C16—C14—H141	112.7	C37—C38—C39	119.7 (3)
C6—C15—C14	114.13 (14)	C37—C38—H381	121.4
C6—C15—H152	107.6	C39—C38—H381	118.9
C14—C15—H152	110.1	C34—C39—C38	120.1 (3)
C6—C15—H151	108.2	C34—C39—H391	118.5
C14—C15—H151	108.6	C38—C39—H391	121.4
H152—C15—H151	108.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H72···O18^i	0.96	2.46	3.306 (3)	146 (1)
C16—H162···O2^ii	0.97	2.57	3.333 (3)	135 (1)

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

(TCL_AC)

Crystal data

C28H36ClNO4	F(000) = 1040
Mr = 486.05	Dx = 1.272 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54180 Å
a = 14.912 (3) Å	Cell parameters from 3207 reflections
b = 9.4993 (16) Å	θ = 5–68°
c = 19.407 (3) Å	µ = 1.60 mm^−1
β = 112.5938 (11)°	T = 150 K
V = 2538.1 (4) Å^3	Plate, colourless
Z = 4	0.30 × 0.14 × 0.04 mm

Data collection

Oxford Diffraction XCALIBUR diffractometer	1813 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.116
φ & ω scans	θmax = 68.1°, θmin = 4.7°
Absorption correction: multi-scan CrysAlisPro, (Agilent, 2011)	h = −17→17
Tmin = 0.79, Tmax = 0.93	k = −11→10
18424 measured reflections	l = −23→23
4509 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	H-atom parameters constrained
wR(F^2) = 0.179	Method = Modified Sheldrick w = 1/[σ^2(F^2) + ( 0.12P)^2 + 0.0P] , where P = (max(Fo^2,0) + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.0002428
4509 reflections	Δρmax = 0.51 e Å^−3
307 parameters	Δρmin = −0.72 e Å^−3
0 restraints

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.

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

	x	y	z	Uiso*/Ueq
Cl1	0.13501 (7)	0.22943 (11)	0.60729 (6)	0.0400
O2	0.3368 (2)	0.1340 (3)	0.61841 (15)	0.0390
C3	0.3857 (3)	0.2590 (4)	0.6119 (2)	0.0340
C4	0.3750 (3)	0.3720 (5)	0.6650 (2)	0.0330
O5	0.3501 (2)	0.4920 (3)	0.64829 (16)	0.0436
O6	0.3982 (2)	0.3178 (3)	0.73297 (14)	0.0392
C7	0.3857 (3)	0.4043 (4)	0.7906 (2)	0.0354
C8	0.2946 (3)	0.3537 (4)	0.8012 (2)	0.0349
C9	0.3122 (3)	0.2227 (4)	0.8489 (2)	0.0335
N10	0.3931 (2)	0.2498 (3)	0.92507 (17)	0.0308
C11	0.3816 (3)	0.3747 (4)	0.9674 (2)	0.0356
C12	0.3091 (3)	0.3292 (5)	0.9998 (3)	0.0491
C13	0.3228 (4)	0.1680 (5)	1.0102 (3)	0.0523
C14	0.3981 (3)	0.1317 (5)	0.9786 (2)	0.0419
C15	0.4808 (3)	0.2549 (4)	0.9043 (2)	0.0314
C16	0.4767 (3)	0.3900 (4)	0.8617 (2)	0.0364
C17	0.4666 (3)	0.1208 (4)	0.8574 (2)	0.0410
C18	0.3546 (3)	0.1011 (4)	0.8191 (2)	0.0424
C19	0.3438 (3)	0.3149 (5)	0.5314 (2)	0.0342
C20	0.3861 (3)	0.4315 (5)	0.5137 (2)	0.0396
C21	0.3508 (3)	0.4848 (5)	0.4416 (2)	0.0435
C22	0.2721 (3)	0.4195 (6)	0.3859 (2)	0.0540
C23	0.2314 (3)	0.3020 (6)	0.4027 (2)	0.0552
C24	0.2656 (3)	0.2512 (5)	0.4757 (2)	0.0443
C25	0.4927 (3)	0.2188 (4)	0.6329 (2)	0.0380
C26	0.5691 (3)	0.2922 (5)	0.6853 (2)	0.0440
C27	0.6651 (3)	0.2524 (5)	0.6999 (2)	0.0489
C28	0.6834 (4)	0.1384 (6)	0.6633 (3)	0.0595
C29	0.6077 (4)	0.0653 (6)	0.6125 (3)	0.0607
C30	0.5121 (4)	0.1053 (5)	0.5971 (2)	0.0517
O31	0.5687 (3)	0.6162 (4)	0.7790 (3)	0.0968
C32	0.5311 (4)	0.7119 (6)	0.7364 (4)	0.0598
C33	0.4880 (5)	0.8325 (6)	0.7593 (3)	0.0954
C34	0.5273 (6)	0.7169 (7)	0.6606 (4)	0.1189
H71	0.3775	0.5051	0.7746	0.0405*
H81	0.2716	0.4300	0.8259	0.0380*
H82	0.2431	0.3327	0.7512	0.0380*
H91	0.2511	0.1927	0.8547	0.0348*
H111	0.4449	0.3995	1.0082	0.0385*
H112	0.3568	0.4575	0.9336	0.0385*
H121	0.3222	0.3764	1.0487	0.0590*
H122	0.2415	0.3518	0.9644	0.0590*
H131	0.3461	0.1427	1.0643	0.0608*
H132	0.2605	0.1178	0.9821	0.0608*
H141	0.4642	0.1276	1.0193	0.0446*
H142	0.3829	0.0392	0.9519	0.0446*
H151	0.5423	0.2504	0.9498	0.0322*
H161	0.4797	0.4714	0.8952	0.0394*
H162	0.5343	0.3928	0.8473	0.0394*
H171	0.4963	0.0390	0.8908	0.0467*
H172	0.4965	0.1301	0.8195	0.0467*
H181	0.3339	0.0088	0.8330	0.0505*
H182	0.3332	0.1069	0.7637	0.0505*
H201	0.4426	0.4785	0.5531	0.0459*
H211	0.3822	0.5690	0.4294	0.0531*
H221	0.2451	0.4603	0.3344	0.0605*
H231	0.1780	0.2510	0.3625	0.0623*
H241	0.2333	0.1683	0.4881	0.0522*
H261	0.5553	0.3734	0.7125	0.0471*
H271	0.7201	0.3069	0.7366	0.0573*
H281	0.7519	0.1088	0.6741	0.0662*
H291	0.6213	−0.0171	0.5859	0.0722*
H301	0.4570	0.0515	0.5599	0.0564*
H331	0.4618	0.9019	0.7175	0.1162*
H332	0.5367	0.8800	0.8040	0.1162*
H333	0.4336	0.7950	0.7720	0.1162*
H341	0.4938	0.8049	0.6354	0.1750*
H342	0.5950	0.7155	0.6621	0.1750*
H343	0.4910	0.6331	0.6323	0.1750*
H21	0.2719	0.1574	0.6117	0.0500*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0381 (5)	0.0392 (6)	0.0341 (5)	−0.0022 (5)	0.0044 (4)	−0.0019 (5)
O2	0.0381 (17)	0.0371 (18)	0.0401 (17)	−0.0035 (14)	0.0132 (14)	−0.0006 (14)
C3	0.037 (2)	0.031 (2)	0.030 (2)	−0.0023 (19)	0.0084 (17)	−0.0029 (18)
C4	0.027 (2)	0.040 (3)	0.030 (2)	0.0001 (19)	0.0088 (17)	0.0024 (19)
O5	0.051 (2)	0.041 (2)	0.0404 (18)	0.0172 (15)	0.0190 (15)	0.0106 (14)
O6	0.0561 (19)	0.0357 (18)	0.0184 (14)	0.0046 (14)	0.0061 (13)	−0.0023 (12)
C7	0.044 (3)	0.032 (2)	0.022 (2)	0.0010 (19)	0.0041 (18)	−0.0043 (17)
C8	0.034 (2)	0.034 (2)	0.029 (2)	0.0024 (19)	0.0034 (18)	0.0044 (18)
C9	0.033 (2)	0.033 (2)	0.0261 (19)	−0.0037 (19)	0.0018 (17)	−0.0031 (18)
N10	0.0356 (18)	0.0227 (19)	0.0264 (16)	−0.0041 (15)	0.0033 (14)	−0.0016 (14)
C11	0.045 (3)	0.033 (2)	0.022 (2)	0.000 (2)	0.0048 (19)	−0.0025 (17)
C12	0.050 (3)	0.053 (3)	0.046 (3)	0.001 (2)	0.021 (2)	0.000 (2)
C13	0.054 (3)	0.051 (3)	0.051 (3)	−0.004 (2)	0.020 (3)	0.012 (2)
C14	0.053 (3)	0.030 (2)	0.033 (2)	−0.008 (2)	0.005 (2)	0.0080 (19)
C15	0.0284 (19)	0.033 (2)	0.0258 (19)	0.0039 (18)	0.0028 (16)	−0.0011 (17)
C16	0.034 (2)	0.037 (3)	0.035 (2)	−0.0066 (19)	0.0091 (19)	−0.0069 (19)
C17	0.051 (3)	0.033 (2)	0.032 (2)	0.013 (2)	0.009 (2)	0.0037 (19)
C18	0.056 (3)	0.026 (2)	0.033 (2)	−0.003 (2)	0.003 (2)	−0.0022 (18)
C19	0.029 (2)	0.040 (3)	0.028 (2)	0.0013 (18)	0.0051 (18)	0.0023 (18)
C20	0.033 (2)	0.049 (3)	0.032 (2)	0.005 (2)	0.0076 (19)	−0.001 (2)
C21	0.041 (3)	0.056 (3)	0.036 (2)	0.005 (2)	0.018 (2)	0.010 (2)
C22	0.045 (3)	0.087 (4)	0.024 (2)	0.006 (3)	0.007 (2)	0.007 (2)
C23	0.040 (3)	0.087 (4)	0.031 (2)	−0.012 (3)	0.005 (2)	−0.001 (3)
C24	0.035 (2)	0.063 (3)	0.031 (2)	−0.008 (2)	0.0089 (18)	0.000 (2)
C25	0.037 (2)	0.038 (3)	0.034 (2)	0.002 (2)	0.0092 (19)	0.005 (2)
C26	0.035 (2)	0.053 (3)	0.039 (2)	0.005 (2)	0.007 (2)	0.008 (2)
C27	0.035 (2)	0.062 (3)	0.042 (3)	0.001 (2)	0.006 (2)	0.010 (2)
C28	0.040 (3)	0.077 (4)	0.063 (3)	0.013 (3)	0.021 (3)	0.019 (3)
C29	0.052 (3)	0.073 (4)	0.060 (3)	0.014 (3)	0.024 (3)	−0.002 (3)
C30	0.050 (3)	0.062 (3)	0.034 (3)	0.005 (3)	0.007 (2)	−0.009 (2)
O31	0.052 (3)	0.062 (3)	0.170 (5)	0.004 (2)	0.035 (3)	0.015 (3)
C32	0.034 (3)	0.046 (3)	0.095 (5)	−0.012 (2)	0.020 (3)	−0.019 (3)
C33	0.154 (7)	0.065 (4)	0.090 (5)	0.038 (4)	0.072 (5)	0.007 (4)
C34	0.206 (9)	0.077 (5)	0.146 (7)	−0.049 (5)	0.148 (7)	−0.045 (5)

Geometric parameters (Å, º)

O2—C3	1.425 (5)	C17—C18	1.557 (6)
O2—H21	0.952	C17—H171	1.000
C3—C4	1.537 (6)	C17—H172	1.000
C3—C19	1.538 (5)	C18—H181	1.000
C3—C25	1.536 (5)	C18—H182	1.000
C4—O5	1.205 (5)	C19—C20	1.381 (6)
C4—O6	1.333 (5)	C19—C24	1.389 (5)
O6—C7	1.457 (5)	C20—C21	1.388 (6)
C7—C8	1.528 (6)	C20—H201	1.000
C7—C16	1.524 (5)	C21—C22	1.398 (6)
C7—H71	1.000	C21—H211	1.000
C8—C9	1.513 (5)	C22—C23	1.369 (7)
C8—H81	1.000	C22—H221	1.000
C8—H82	1.000	C23—C24	1.393 (6)
C9—N10	1.529 (4)	C23—H231	1.000
C9—C18	1.533 (6)	C24—H241	1.000
C9—H91	1.000	C25—C26	1.388 (6)
N10—C11	1.491 (5)	C25—C30	1.372 (6)
N10—C14	1.511 (5)	C26—C27	1.400 (6)
N10—C15	1.511 (5)	C26—H261	1.000
C11—C12	1.506 (6)	C27—C28	1.380 (7)
C11—H111	1.000	C27—H271	1.000
C11—H112	1.000	C28—C29	1.369 (7)
C12—C13	1.547 (6)	C28—H281	1.000
C12—H121	1.000	C29—C30	1.393 (7)
C12—H122	1.000	C29—H291	1.000
C13—C14	1.512 (7)	C30—H301	1.000
C13—H131	1.000	O31—C32	1.212 (6)
C13—H132	1.000	C32—C33	1.463 (7)
C14—H141	1.000	C32—C34	1.451 (9)
C14—H142	1.000	C33—H331	1.000
C15—C16	1.515 (5)	C33—H332	1.000
C15—C17	1.532 (5)	C33—H333	1.000
C15—H151	1.000	C34—H341	1.000
C16—H161	1.000	C34—H342	1.000
C16—H162	1.000	C34—H343	1.000
C3—O2—H21	108.8	C15—C16—H161	108.5
O2—C3—C4	109.5 (3)	C7—C16—H162	107.9
O2—C3—C19	110.8 (3)	C15—C16—H162	108.4
C4—C3—C19	109.5 (3)	H161—C16—H162	109.5
O2—C3—C25	106.5 (3)	C15—C17—C18	105.1 (3)
C4—C3—C25	111.2 (3)	C15—C17—H171	109.6
C19—C3—C25	109.3 (3)	C18—C17—H171	110.1
C3—C4—O5	125.6 (4)	C15—C17—H172	111.4
C3—C4—O6	109.9 (3)	C18—C17—H172	111.1
O5—C4—O6	124.6 (4)	H171—C17—H172	109.5
C4—O6—C7	118.8 (3)	C9—C18—C17	104.6 (3)
O6—C7—C8	107.9 (3)	C9—C18—H181	110.2
O6—C7—C16	108.2 (3)	C17—C18—H181	111.3
C8—C7—C16	112.3 (3)	C9—C18—H182	111.0
O6—C7—H71	109.7	C17—C18—H182	110.3
C8—C7—H71	109.5	H181—C18—H182	109.5
C16—C7—H71	109.1	C3—C19—C20	118.9 (3)
C7—C8—C9	112.8 (3)	C3—C19—C24	122.2 (4)
C7—C8—H81	108.8	C20—C19—C24	118.9 (4)
C9—C8—H81	108.3	C19—C20—C21	120.7 (4)
C7—C8—H82	108.9	C19—C20—H201	120.0
C9—C8—H82	108.5	C21—C20—H201	119.3
H81—C8—H82	109.5	C20—C21—C22	119.9 (5)
C8—C9—N10	109.9 (3)	C20—C21—H211	119.9
C8—C9—C18	112.8 (4)	C22—C21—H211	120.2
N10—C9—C18	101.8 (3)	C21—C22—C23	119.6 (4)
C8—C9—H91	110.6	C21—C22—H221	119.8
N10—C9—H91	110.8	C23—C22—H221	120.6
C18—C9—H91	110.7	C22—C23—C24	120.1 (4)
C9—N10—C11	116.8 (3)	C22—C23—H231	120.0
C9—N10—C14	110.5 (3)	C24—C23—H231	119.8
C11—N10—C14	101.4 (3)	C23—C24—C19	120.7 (5)
C9—N10—C15	101.0 (3)	C23—C24—H241	119.8
C11—N10—C15	114.7 (3)	C19—C24—H241	119.6
C14—N10—C15	112.9 (3)	C3—C25—C26	123.0 (4)
N10—C11—C12	104.8 (3)	C3—C25—C30	117.4 (4)
N10—C11—H111	110.5	C26—C25—C30	119.6 (4)
C12—C11—H111	110.4	C25—C26—C27	120.0 (5)
N10—C11—H112	110.8	C25—C26—H261	119.9
C12—C11—H112	110.8	C27—C26—H261	120.1
H111—C11—H112	109.5	C26—C27—C28	119.8 (4)
C11—C12—C13	105.0 (4)	C26—C27—H271	120.1
C11—C12—H121	110.9	C28—C27—H271	120.1
C13—C12—H121	110.6	C27—C28—C29	119.8 (5)
C11—C12—H122	110.3	C27—C28—H281	120.1
C13—C12—H122	110.5	C29—C28—H281	120.1
H121—C12—H122	109.5	C28—C29—C30	120.6 (5)
C12—C13—C14	104.7 (4)	C28—C29—H291	119.6
C12—C13—H131	110.6	C30—C29—H291	119.8
C14—C13—H131	111.0	C29—C30—C25	120.2 (5)
C12—C13—H132	110.6	C29—C30—H301	120.4
C14—C13—H132	110.4	C25—C30—H301	119.5
H131—C13—H132	109.5	O31—C32—C33	121.5 (6)
C13—C14—N10	105.2 (4)	O31—C32—C34	122.9 (6)
C13—C14—H141	110.4	C33—C32—C34	115.5 (6)
N10—C14—H141	110.1	C32—C33—H331	110.5
C13—C14—H142	110.8	C32—C33—H332	111.1
N10—C14—H142	110.8	H331—C33—H332	109.5
H141—C14—H142	109.5	C32—C33—H333	106.7
N10—C15—C16	108.4 (3)	H331—C33—H333	109.5
N10—C15—C17	101.3 (3)	H332—C33—H333	109.5
C16—C15—C17	114.4 (3)	C32—C34—H341	109.9
N10—C15—H151	110.9	C32—C34—H342	109.0
C16—C15—H151	110.4	H341—C34—H342	109.5
C17—C15—H151	111.1	C32—C34—H343	109.5
C7—C16—C15	113.9 (3)	H341—C34—H343	109.5
C7—C16—H161	108.7	H342—C34—H343	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H91···O5^i	1.00	2.42	3.280 (7)	144 (1)
C28—H281···O31^ii	1.00	2.47	3.432 (7)	160 (1)

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

(TR_SAC1)

Crystal data

C32H36.00N2O7S	F(000) = 1256.000
Mr = 592.71	Dx = 1.362 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 14.2061 (4) Å	Cell parameters from 5301 reflections
b = 12.6581 (3) Å	θ = 5–70°
c = 17.5097 (4) Å	µ = 1.43 mm^−1
β = 113.360 (3)°	T = 190 K
V = 2890.53 (14) Å^3	Plate, colour less
Z = 4	0.80 × 0.40 × 0.10 mm

Data collection

Oxford Diffraction XCALIBUR diffractometer	4135 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.044
ω/2θ scans	θmax = 70.1°, θmin = 4.5°
Absorption correction: multi-scan CrysAlis, (Oxford Diffraction, 2002)	h = −16→16
Tmin = 0.77, Tmax = 0.87	k = −14→12
12265 measured reflections	l = −18→21
5187 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are: 283. 459. 279. 117. 26.8
S = 0.94	(Δ/σ)max = 0.001
5187 reflections	Δρmax = 0.30 e Å^−3
398 parameters	Δρmin = −0.38 e Å^−3
52 restraints

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O13	0.86680 (10)	0.18887 (11)	0.45904 (8)	0.0262
C14	0.85100 (15)	0.12984 (16)	0.39178 (12)	0.0242
O15	0.91679 (11)	0.10441 (12)	0.36835 (9)	0.0329
C16	0.73706 (16)	0.09808 (16)	0.34562 (12)	0.0256
O17	0.73132 (12)	0.01236 (12)	0.29214 (9)	0.0336
C18	0.69630 (15)	0.05842 (16)	0.40928 (13)	0.0259
C19	0.65818 (17)	0.12760 (18)	0.45151 (13)	0.0305
C20	0.62635 (17)	0.09124 (19)	0.51182 (14)	0.0345
C21	0.63199 (17)	−0.01549 (19)	0.53067 (14)	0.0345
C22	0.66903 (16)	−0.08546 (18)	0.48888 (14)	0.0326
C23	0.70141 (16)	−0.04899 (17)	0.42834 (13)	0.0296
C24	0.67644 (16)	0.19254 (17)	0.29529 (12)	0.0269
C25	0.57010 (17)	0.1832 (2)	0.25425 (14)	0.0359
C26	0.51243 (18)	0.2638 (2)	0.20345 (14)	0.0405
C27	0.56031 (19)	0.3544 (2)	0.19299 (14)	0.0400
C28	0.66491 (19)	0.3646 (2)	0.23282 (14)	0.0399
C29	0.72309 (17)	0.28381 (18)	0.28366 (13)	0.0329
C30	0.97328 (15)	0.22098 (17)	0.50775 (12)	0.0270
C31	0.97025 (16)	0.32398 (16)	0.55139 (13)	0.0289
C32	0.96101 (16)	0.31023 (16)	0.63449 (13)	0.0263
N33	1.04835 (13)	0.23965 (14)	0.69134 (10)	0.0265
C34	1.15605 (16)	0.2706 (2)	0.70458 (14)	0.0387
C37	1.05310 (18)	0.24104 (19)	0.77960 (13)	0.0361
C38	1.01387 (17)	0.13307 (16)	0.64979 (13)	0.0309
C39	1.02861 (17)	0.13236 (18)	0.56812 (13)	0.0327
C40	0.90169 (18)	0.12983 (17)	0.63893 (14)	0.0337
C41	0.86635 (16)	0.24614 (18)	0.62655 (14)	0.0317
H171	0.7588	0.0314	0.2601	0.0510*
H191	0.6541	0.1992	0.4383	0.0374*
H201	0.5989	0.1387	0.5394	0.0416*
H211	0.6096	−0.0401	0.5713	0.0413*
H221	0.6726	−0.1576	0.5012	0.0409*
H231	0.7255	−0.0964	0.3987	0.0355*
H251	0.5378	0.1203	0.2611	0.0428*
H261	0.4404	0.2568	0.1755	0.0491*
H271	0.5216	0.4108	0.1586	0.0484*
H281	0.6978	0.4276	0.2253	0.0492*
H291	0.7955	0.2906	0.3103	0.0400*
H301	1.0052	0.2348	0.4680	0.0319*
H311	1.0320	0.3642	0.5588	0.0352*
H312	0.9109	0.3657	0.5151	0.0351*
H321	0.9639	0.3793	0.6626	0.0330*
C350	1.1861 (2)	0.3520 (3)	0.77190 (19)	0.0463	0.853 (7)
C351	1.2209 (5)	0.2837 (18)	0.7926 (6)	0.0545	0.147 (7)
C360	1.1191 (3)	0.3342 (3)	0.8199 (2)	0.0496	0.853 (7)
C361	1.1521 (10)	0.2917 (16)	0.8363 (6)	0.0481	0.147 (7)
H381	1.0569	0.0788	0.6869	0.0366*
H391	1.1011	0.1369	0.5801	0.0400*
H392	1.0040	0.0649	0.5406	0.0398*
H401	0.8978	0.1011	0.6890	0.0400*
H402	0.8621	0.0875	0.5908	0.0405*
H411	0.8412	0.2672	0.6696	0.0380*
H412	0.8118	0.2569	0.5719	0.0366*
H3501	1.2574	0.3447	0.8087	0.0560*	0.853 (7)
H3502	1.1740	0.4217	0.7472	0.0559*	0.853 (7)
H3511	1.2623	0.3471	0.8011	0.0702*	0.147 (7)
H3512	1.2650	0.2226	0.8131	0.0701*	0.147 (7)
H3601	1.0757	0.3956	0.8118	0.0601*	0.853 (7)
H3602	1.1578	0.3241	0.8787	0.0597*	0.853 (7)
H3611	1.1811	0.2541	0.8887	0.0599*	0.147 (7)
H3612	1.1408	0.3650	0.8468	0.0600*	0.147 (7)
S1	0.75785 (4)	0.56533 (4)	0.46056 (3)	0.0287
O2	0.81143 (12)	0.51706 (13)	0.41482 (10)	0.0378
O3	0.72113 (14)	0.67047 (13)	0.43331 (11)	0.0453
N4	0.82556 (14)	0.56125 (15)	0.55880 (11)	0.0326
C5	0.77846 (16)	0.50502 (17)	0.59943 (13)	0.0298
O6	0.81463 (13)	0.49293 (14)	0.67573 (10)	0.0395
C7	0.67914 (16)	0.45657 (16)	0.54188 (13)	0.0285
C8	0.65733 (16)	0.48266 (17)	0.45997 (13)	0.0284
C9	0.57088 (17)	0.4473 (2)	0.39487 (15)	0.0373
C10	0.50445 (19)	0.3835 (2)	0.41523 (17)	0.0436
C11	0.52476 (19)	0.3572 (2)	0.49691 (18)	0.0428
C12	0.61265 (18)	0.39283 (18)	0.56155 (16)	0.0365
H91	0.5574	0.4656	0.3399	0.0449*
H101	0.4452	0.3587	0.3725	0.0526*
H111	0.4780	0.3143	0.5088	0.0508*
H121	0.6270	0.3760	0.6167	0.0447*
O42	0.94936 (13)	0.42068 (15)	0.35540 (12)	0.0486
H421	1.0138	0.4282	0.3840	0.0734*
H422	0.9164	0.4473	0.3826	0.0732*
H341	1.2007	0.2114	0.7214	0.0470*	0.853 (7)
H342	1.1576	0.2995	0.6550	0.0470*	0.853 (7)
H343	1.1845	0.2176	0.6819	0.0470*	0.147 (7)
H344	1.1538	0.3358	0.6767	0.0470*	0.147 (7)
H371	1.0505	0.1707	0.7977	0.0438*	0.147 (7)
H372	0.9966	0.2800	0.7810	0.0438*	0.147 (7)
H373	1.0831	0.1779	0.8082	0.0438*	0.853 (7)
H374	0.9865	0.2494	0.7794	0.0438*	0.853 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O13	0.0227 (7)	0.0298 (8)	0.0245 (7)	−0.0005 (6)	0.0077 (6)	−0.0040 (6)
C14	0.0283 (10)	0.0228 (10)	0.0216 (9)	0.0015 (8)	0.0102 (8)	0.0023 (8)
O15	0.0310 (8)	0.0354 (8)	0.0349 (8)	0.0022 (6)	0.0157 (7)	−0.0059 (7)
C16	0.0280 (10)	0.0252 (10)	0.0233 (10)	−0.0013 (8)	0.0097 (8)	−0.0051 (8)
O17	0.0429 (9)	0.0297 (8)	0.0330 (8)	−0.0073 (7)	0.0202 (7)	−0.0100 (6)
C18	0.0229 (10)	0.0279 (10)	0.0258 (10)	−0.0030 (8)	0.0086 (8)	−0.0019 (8)
C19	0.0335 (11)	0.0284 (11)	0.0299 (11)	0.0001 (9)	0.0129 (9)	0.0003 (9)
C20	0.0324 (12)	0.0411 (13)	0.0336 (12)	0.0020 (10)	0.0167 (10)	−0.0020 (10)
C21	0.0301 (11)	0.0445 (13)	0.0291 (11)	−0.0029 (10)	0.0118 (9)	0.0061 (10)
C22	0.0284 (11)	0.0310 (11)	0.0339 (12)	−0.0039 (9)	0.0076 (9)	0.0053 (9)
C23	0.0245 (10)	0.0300 (11)	0.0334 (11)	0.0000 (8)	0.0104 (9)	−0.0012 (9)
C24	0.0280 (10)	0.0319 (11)	0.0198 (9)	0.0000 (9)	0.0085 (8)	−0.0022 (8)
C25	0.0300 (11)	0.0421 (13)	0.0314 (11)	−0.0057 (10)	0.0077 (9)	−0.0022 (10)
C26	0.0286 (11)	0.0558 (16)	0.0298 (11)	0.0024 (11)	0.0039 (9)	0.0001 (11)
C27	0.0374 (13)	0.0473 (14)	0.0292 (11)	0.0092 (11)	0.0067 (10)	0.0076 (10)
C28	0.0402 (13)	0.0383 (13)	0.0358 (12)	−0.0020 (10)	0.0092 (10)	0.0094 (10)
C29	0.0269 (11)	0.0388 (12)	0.0285 (11)	−0.0028 (9)	0.0063 (9)	0.0028 (9)
C30	0.0226 (10)	0.0307 (11)	0.0253 (10)	−0.0017 (8)	0.0069 (8)	−0.0024 (8)
C31	0.0307 (11)	0.0230 (10)	0.0302 (11)	−0.0030 (8)	0.0090 (9)	0.0015 (8)
C32	0.0303 (11)	0.0186 (10)	0.0301 (10)	0.0013 (8)	0.0122 (9)	−0.0004 (8)
N33	0.0283 (9)	0.0252 (9)	0.0246 (8)	−0.0008 (7)	0.0090 (7)	0.0008 (7)
C34	0.0270 (11)	0.0528 (15)	0.0336 (12)	−0.0038 (10)	0.0092 (9)	0.0000 (11)
C37	0.0440 (13)	0.0402 (13)	0.0241 (10)	−0.0045 (10)	0.0133 (9)	0.0024 (9)
C38	0.0375 (12)	0.0189 (10)	0.0297 (11)	0.0051 (9)	0.0062 (9)	0.0014 (8)
C39	0.0320 (11)	0.0322 (12)	0.0295 (11)	0.0085 (9)	0.0076 (9)	−0.0038 (9)
C40	0.0394 (12)	0.0276 (11)	0.0329 (11)	−0.0076 (9)	0.0130 (10)	0.0004 (9)
C41	0.0295 (11)	0.0322 (12)	0.0348 (11)	−0.0005 (9)	0.0141 (9)	−0.0032 (9)
C350	0.0433 (17)	0.048 (2)	0.0421 (16)	−0.0189 (15)	0.0113 (14)	−0.0084 (14)
C351	0.043 (6)	0.058 (7)	0.045 (6)	−0.007 (6)	−0.001 (5)	0.003 (6)
C360	0.060 (2)	0.053 (2)	0.0354 (16)	−0.0195 (17)	0.0190 (15)	−0.0132 (15)
C361	0.051 (6)	0.045 (7)	0.034 (6)	−0.008 (6)	0.002 (5)	0.005 (6)
S1	0.0304 (3)	0.0282 (3)	0.0303 (3)	0.0030 (2)	0.0151 (2)	0.0035 (2)
O2	0.0384 (9)	0.0456 (10)	0.0376 (9)	0.0034 (7)	0.0238 (7)	0.0005 (7)
O3	0.0548 (11)	0.0298 (9)	0.0521 (10)	0.0110 (8)	0.0221 (9)	0.0131 (8)
N4	0.0333 (10)	0.0335 (10)	0.0326 (10)	−0.0041 (8)	0.0149 (8)	0.0000 (8)
C5	0.0320 (11)	0.0283 (11)	0.0317 (12)	0.0047 (9)	0.0154 (9)	−0.0007 (9)
O6	0.0434 (9)	0.0480 (10)	0.0298 (8)	0.0001 (8)	0.0174 (7)	0.0012 (7)
C7	0.0302 (11)	0.0252 (10)	0.0344 (11)	0.0053 (8)	0.0176 (9)	0.0004 (9)
C8	0.0269 (10)	0.0281 (11)	0.0341 (11)	0.0054 (9)	0.0162 (9)	−0.0002 (9)
C9	0.0330 (12)	0.0412 (13)	0.0359 (12)	0.0048 (10)	0.0118 (10)	−0.0041 (10)
C10	0.0309 (12)	0.0415 (14)	0.0543 (15)	−0.0033 (10)	0.0127 (11)	−0.0103 (12)
C11	0.0356 (13)	0.0335 (13)	0.0666 (17)	−0.0016 (10)	0.0280 (12)	−0.0014 (12)
C12	0.0389 (13)	0.0322 (12)	0.0450 (13)	0.0034 (10)	0.0238 (11)	0.0039 (10)
O42	0.0396 (9)	0.0569 (11)	0.0534 (11)	−0.0036 (8)	0.0226 (8)	−0.0210 (9)

Geometric parameters (Å, º)

O13—C14	1.336 (2)	C34—H342	0.950
O13—C30	1.469 (2)	C37—C360	1.498 (3)
C14—O15	1.204 (2)	C37—H373	0.949
C14—C16	1.548 (3)	C37—H374	0.951
C16—O17	1.414 (2)	C38—C39	1.525 (3)
C16—C18	1.530 (3)	C38—C40	1.529 (3)
C16—C24	1.532 (3)	C38—H381	0.977
O17—H171	0.835	C39—H391	0.968
C18—C19	1.387 (3)	C39—H392	0.974
C18—C23	1.395 (3)	C40—C41	1.543 (3)
C19—C20	1.382 (3)	C40—H401	0.970
C19—H191	0.931	C40—H402	0.968
C20—C21	1.385 (3)	C41—H411	0.990
C20—H201	0.946	C41—H412	0.973
C21—C22	1.379 (3)	C350—C360	1.515 (3)
C21—H211	0.941	C350—H3501	0.966
C22—C23	1.391 (3)	C350—H3502	0.967
C22—H221	0.935	C351—C361	1.463 (8)
C23—H231	0.942	C351—H3511	0.971
C24—C25	1.397 (3)	C351—H3512	0.969
C24—C29	1.386 (3)	C360—H3601	0.968
C25—C26	1.387 (3)	C360—H3602	0.964
C25—H251	0.951	C361—H3611	0.969
C26—C27	1.383 (4)	C361—H3612	0.972
C26—H261	0.947	S1—O2	1.4413 (16)
C27—C28	1.374 (3)	S1—O3	1.4401 (17)
C27—H271	0.955	S1—N4	1.6046 (19)
C28—C29	1.392 (3)	S1—C8	1.767 (2)
C28—H281	0.960	N4—C5	1.356 (3)
C29—H291	0.950	C5—O6	1.236 (3)
C30—C31	1.520 (3)	C5—C7	1.502 (3)
C30—C39	1.528 (3)	C7—C8	1.382 (3)
C30—H301	0.985	C7—C12	1.386 (3)
C31—C32	1.522 (3)	C8—C9	1.378 (3)
C31—H311	0.977	C9—C10	1.392 (4)
C31—H312	0.984	C9—H91	0.934
C32—N33	1.533 (3)	C10—C11	1.383 (4)
C32—C41	1.529 (3)	C10—H101	0.932
C32—H321	0.996	C11—C12	1.387 (4)
N33—C34	1.506 (3)	C11—H111	0.943
N33—C37	1.520 (3)	C12—H121	0.930
N33—C38	1.519 (3)	O42—H421	0.857
C34—C350	1.495 (3)	O42—H422	0.859
C34—H341	0.950
C14—O13—C30	116.16 (15)	N33—C37—H374	110.7
O13—C14—O15	124.61 (19)	C360—C37—H374	110.6
O13—C14—C16	112.38 (16)	H373—C37—H374	109.5
O15—C14—C16	123.01 (18)	N33—C38—C39	108.44 (17)
C14—C16—O17	108.58 (16)	N33—C38—C40	101.87 (17)
C14—C16—C18	108.91 (16)	C39—C38—C40	114.02 (18)
O17—C16—C18	106.95 (16)	N33—C38—H381	107.9
C14—C16—C24	109.30 (17)	C39—C38—H381	109.7
O17—C16—C24	110.26 (16)	C40—C38—H381	114.3
C18—C16—C24	112.73 (17)	C30—C39—C38	114.84 (17)
C16—O17—H171	107.7	C30—C39—H391	108.5
C16—C18—C19	121.44 (19)	C38—C39—H391	109.1
C16—C18—C23	119.68 (18)	C30—C39—H392	108.4
C19—C18—C23	118.8 (2)	C38—C39—H392	108.2
C18—C19—C20	120.8 (2)	H391—C39—H392	107.6
C18—C19—H191	118.7	C38—C40—C41	104.89 (17)
C20—C19—H191	120.5	C38—C40—H401	109.1
C19—C20—C21	120.1 (2)	C41—C40—H401	110.6
C19—C20—H201	120.3	C38—C40—H402	109.9
C21—C20—H201	119.6	C41—C40—H402	111.2
C20—C21—C22	119.9 (2)	H401—C40—H402	110.9
C20—C21—H211	119.9	C40—C41—C32	105.55 (17)
C22—C21—H211	120.2	C40—C41—H411	110.2
C21—C22—C23	120.1 (2)	C32—C41—H411	110.9
C21—C22—H221	120.2	C40—C41—H412	111.1
C23—C22—H221	119.7	C32—C41—H412	110.1
C18—C23—C22	120.3 (2)	H411—C41—H412	109.0
C18—C23—H231	119.0	C34—C350—C360	106.80 (9)
C22—C23—H231	120.7	C34—C350—H3501	110.8
C16—C24—C25	118.47 (19)	C360—C350—H3501	109.8
C16—C24—C29	122.86 (18)	C34—C350—H3502	109.4
C25—C24—C29	118.5 (2)	C360—C350—H3502	110.1
C24—C25—C26	120.7 (2)	H3501—C350—H3502	109.8
C24—C25—H251	118.9	C34—C351—C361	106.73 (10)
C26—C25—H251	120.4	C34—C351—H3511	110.2
C25—C26—C27	119.9 (2)	C361—C351—H3511	110.6
C25—C26—H261	120.3	C34—C351—H3512	110.2
C27—C26—H261	119.8	C361—C351—H3512	109.3
C26—C27—C28	120.0 (2)	H3511—C351—H3512	109.8
C26—C27—H271	120.9	C350—C360—C37	105.64 (9)
C28—C27—H271	119.1	C350—C360—H3601	107.7
C27—C28—C29	120.3 (2)	C37—C360—H3601	108.6
C27—C28—H281	119.7	C350—C360—H3602	113.3
C29—C28—H281	120.0	C37—C360—H3602	112.6
C28—C29—C24	120.6 (2)	H3601—C360—H3602	108.9
C28—C29—H291	120.1	C37—C361—C351	105.57 (10)
C24—C29—H291	119.4	C37—C361—H3611	110.5
O13—C30—C31	107.53 (16)	C351—C361—H3611	109.9
O13—C30—C39	109.11 (17)	C37—C361—H3612	110.5
C31—C30—C39	113.03 (17)	C351—C361—H3612	111.1
O13—C30—H301	107.2	H3611—C361—H3612	109.3
C31—C30—H301	108.4	O2—S1—O3	114.17 (10)
C39—C30—H301	111.3	O2—S1—N4	110.97 (10)
C30—C31—C32	114.38 (17)	O3—S1—N4	111.68 (11)
C30—C31—H311	108.1	O2—S1—C8	110.44 (10)
C32—C31—H311	110.2	O3—S1—C8	111.07 (10)
C30—C31—H312	108.8	N4—S1—C8	97.28 (10)
C32—C31—H312	107.6	S1—N4—C5	111.63 (15)
H311—C31—H312	107.5	N4—C5—O6	123.5 (2)
C31—C32—N33	109.45 (16)	N4—C5—C7	112.97 (18)
C31—C32—C41	112.33 (17)	O6—C5—C7	123.5 (2)
N33—C32—C41	101.89 (16)	C5—C7—C8	111.30 (19)
C31—C32—H321	111.7	C5—C7—C12	128.5 (2)
N33—C32—H321	109.0	C8—C7—C12	120.2 (2)
C41—C32—H321	111.9	S1—C8—C7	106.70 (16)
C32—N33—C34	117.37 (17)	S1—C8—C9	130.58 (18)
C32—N33—C37	110.59 (16)	C7—C8—C9	122.7 (2)
C34—N33—C37	101.99 (15)	C8—C9—C10	116.7 (2)
C32—N33—C38	100.51 (15)	C8—C9—H91	121.5
C34—N33—C38	114.84 (17)	C10—C9—H91	121.8
C37—N33—C38	111.91 (16)	C9—C10—C11	121.3 (2)
N33—C34—C350	104.81 (17)	C9—C10—H101	118.6
N33—C34—H341	110.7	C11—C10—H101	120.1
C350—C34—H341	110.6	C10—C11—C12	121.1 (2)
N33—C34—H342	110.5	C10—C11—H111	119.4
C350—C34—H342	110.6	C12—C11—H111	119.5
H341—C34—H342	109.5	C11—C12—C7	117.9 (2)
N33—C37—C360	104.79 (17)	C11—C12—H121	121.9
N33—C37—H373	110.8	C7—C12—H121	120.1
C360—C37—H373	110.4	H421—O42—H422	108.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O17—H171···O6^i	0.84	1.96	2.734 (4)	154 (1)
C26—H261···O3^ii	0.95	2.57	3.441 (4)	152 (1)
C29—H291···O42	0.95	2.60	3.422 (4)	145 (1)
C31—H311···O2^iii	0.98	2.57	3.544 (4)	175 (1)
C38—H381···O15^iv	0.98	2.60	3.218 (4)	122 (1)
O42—H421···N4^iii	0.86	2.10	2.954 (4)	173 (1)
O42—H422···O2	0.86	2.00	2.833 (4)	164 (1)
C37—H371···O42^v	0.95	2.36	3.110 (4)	135 (1)

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

(TR_SAC2)

Crystal data

C32H36N2O7S	F(000) = 1256
Mr = 592.71	Dx = 1.388 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 13.2637 (2) Å	Cell parameters from 16786 reflections
b = 12.7583 (2) Å	θ = 5–76°
c = 17.5667 (4) Å	µ = 1.46 mm^−1
β = 107.448 (2)°	T = 190 K
V = 2835.90 (10) Å^3	Plate, color less
Z = 4	0.70 × 0.30 × 0.10 mm

Data collection

Unknown diffractometer	5622 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.038
ω/2θ scans	θmax = 76.7°, θmin = 4.4°
Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997)	h = −16→16
Tmin = 0.49, Tmax = 0.86	k = −16→15
23048 measured reflections	l = −16→21
5810 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.135	Method = Modified Sheldrick w = 1/[σ^2(F^2) + ( 0.07P)^2 + 3.82P] , where P = (max(Fo^2,0) + 2Fc^2)/3
S = 0.92	(Δ/σ)max = 0.001
5806 reflections	Δρmax = 0.68 e Å^−3
379 parameters	Δρmin = −0.56 e Å^−3
0 restraints

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.

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

	x	y	z	Uiso*/Ueq
S1	0.22302 (4)	1.10184 (4)	0.50189 (3)	0.0292
O2	0.19071 (14)	1.20656 (13)	0.51675 (11)	0.0437
O3	0.22538 (14)	1.02818 (15)	0.56378 (10)	0.0447
N4	0.15347 (13)	1.06073 (14)	0.41618 (10)	0.0284
C5	0.21235 (15)	1.04753 (15)	0.36588 (11)	0.0252
O6	0.17622 (11)	1.01568 (12)	0.29652 (8)	0.0313
C7	0.32558 (16)	1.07809 (15)	0.40258 (12)	0.0270
C8	0.34457 (16)	1.10905 (15)	0.48091 (12)	0.0281
C9	0.44352 (17)	1.13851 (17)	0.52921 (13)	0.0335
C10	0.52508 (17)	1.13625 (17)	0.49465 (15)	0.0363
C11	0.50750 (18)	1.10763 (18)	0.41619 (15)	0.0375
C12	0.40766 (17)	1.07782 (17)	0.36827 (13)	0.0330
O13	0.15177 (10)	0.68619 (10)	0.53317 (7)	0.0228
C14	0.16343 (14)	0.62220 (14)	0.59539 (10)	0.0215
O15	0.09299 (11)	0.59627 (11)	0.62156 (8)	0.0295
C16	0.27821 (14)	0.58323 (14)	0.63076 (11)	0.0224
O17	0.27700 (11)	0.49411 (11)	0.67868 (8)	0.0282
C18	0.34695 (15)	0.66918 (16)	0.68134 (11)	0.0255
C19	0.45447 (16)	0.64866 (19)	0.71589 (12)	0.0337
C20	0.51997 (18)	0.7227 (2)	0.76406 (13)	0.0423
C21	0.4796 (2)	0.8176 (2)	0.77929 (14)	0.0440
C22	0.3739 (2)	0.8383 (2)	0.74615 (14)	0.0421
C23	0.30750 (17)	0.76444 (17)	0.69721 (12)	0.0323
C24	0.31792 (14)	0.54706 (15)	0.56183 (10)	0.0223
C25	0.30161 (15)	0.44426 (16)	0.53438 (12)	0.0269
C26	0.33059 (16)	0.41394 (17)	0.46791 (13)	0.0315
C27	0.37515 (16)	0.48494 (18)	0.42831 (12)	0.0315
C28	0.39247 (16)	0.58711 (17)	0.45577 (12)	0.0300
C29	0.36463 (15)	0.61750 (16)	0.52241 (11)	0.0255
C30	0.04289 (14)	0.71923 (15)	0.49152 (11)	0.0235
C31	0.04873 (15)	0.82405 (14)	0.45125 (11)	0.0241
C32	0.06196 (14)	0.81467 (14)	0.36827 (11)	0.0230
N33	−0.02557 (12)	0.74606 (12)	0.31501 (9)	0.0222
C34	0.00859 (15)	0.63897 (14)	0.35171 (11)	0.0248
C35	−0.01155 (15)	0.63366 (15)	0.43273 (12)	0.0260
C36	0.12540 (15)	0.63706 (16)	0.35618 (12)	0.0281
C37	0.16170 (15)	0.75270 (16)	0.36971 (12)	0.0278
C38	−0.02469 (16)	0.75285 (17)	0.22880 (11)	0.0297
C39	−0.09322 (19)	0.8463 (2)	0.19550 (14)	0.0421
C40	−0.1756 (2)	0.8488 (2)	0.23939 (15)	0.0463
C41	−0.13897 (15)	0.77411 (17)	0.30861 (12)	0.0295
O43	0.08434 (14)	0.92460 (16)	0.64335 (11)	0.0506
H91	0.4565	1.1591	0.5849	0.0402*
H101	0.5923	1.1531	0.5274	0.0432*
H111	0.5677	1.1042	0.3964	0.0456*
H121	0.3953	1.0581	0.3133	0.0405*
H191	0.4819	0.5825	0.7065	0.0393*
H201	0.5913	0.7077	0.7866	0.0515*
H211	0.5252	0.8675	0.8124	0.0526*
H221	0.3458	0.9032	0.7566	0.0492*
H231	0.2360	0.7809	0.6741	0.0387*
H251	0.2735	0.3953	0.5621	0.0307*
H261	0.3208	0.3432	0.4502	0.0376*
H271	0.3941	0.4634	0.3827	0.0368*
H281	0.4225	0.6351	0.4291	0.0364*
H291	0.3755	0.6869	0.5413	0.0318*
H301	0.0054	0.7288	0.5316	0.0278*
H312	0.1061	0.8652	0.4839	0.0282*
H311	−0.0156	0.8623	0.4469	0.0279*
H321	0.0601	0.8831	0.3447	0.0274*
H341	−0.0324	0.5844	0.3153	0.0298*
H351	−0.0869	0.6393	0.4247	0.0315*
H352	0.0107	0.5648	0.4548	0.0307*
H361	0.1643	0.5927	0.4011	0.0337*
H362	0.1339	0.6112	0.3070	0.0335*
H371	0.2136	0.7603	0.4212	0.0330*
H372	0.1919	0.7780	0.3290	0.0322*
H382	0.0474	0.7598	0.2271	0.0349*
H381	−0.0554	0.6884	0.2021	0.0357*
H392	−0.0501	0.9106	0.2060	0.0515*
H391	−0.1241	0.8382	0.1395	0.0504*
H402	−0.1840	0.9203	0.2571	0.0574*
H401	−0.2430	0.8240	0.2046	0.0573*
H412	−0.1427	0.8032	0.3591	0.0342*
H411	−0.1788	0.7103	0.2964	0.0351*
H171	0.2424	0.5031	0.7087	0.0419*
H431	0.1111	0.9567	0.6126	0.0764*
H432	0.0196	0.9325	0.6229	0.0763*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0291 (3)	0.0356 (3)	0.0260 (3)	−0.00564 (19)	0.01276 (19)	−0.00625 (19)
O2	0.0452 (9)	0.0407 (9)	0.0517 (10)	−0.0026 (7)	0.0242 (8)	−0.0138 (8)
O3	0.0529 (10)	0.0527 (10)	0.0303 (8)	−0.0116 (8)	0.0153 (7)	0.0030 (7)
N4	0.0267 (8)	0.0338 (9)	0.0263 (8)	−0.0002 (7)	0.0105 (7)	−0.0001 (7)
C5	0.0251 (9)	0.0269 (9)	0.0235 (9)	0.0010 (7)	0.0073 (7)	0.0004 (7)
O6	0.0298 (7)	0.0410 (8)	0.0219 (7)	−0.0027 (6)	0.0060 (5)	−0.0038 (6)
C7	0.0281 (10)	0.0258 (9)	0.0267 (10)	0.0009 (7)	0.0077 (8)	0.0012 (7)
C8	0.0314 (10)	0.0254 (9)	0.0278 (10)	−0.0019 (7)	0.0093 (8)	0.0002 (8)
C9	0.0361 (11)	0.0331 (11)	0.0290 (10)	−0.0057 (9)	0.0065 (8)	−0.0009 (8)
C10	0.0254 (10)	0.0312 (10)	0.0483 (13)	−0.0063 (8)	0.0048 (9)	0.0058 (9)
C11	0.0298 (11)	0.0402 (12)	0.0455 (13)	−0.0023 (9)	0.0156 (9)	0.0060 (10)
C12	0.0332 (10)	0.0377 (11)	0.0308 (11)	−0.0016 (9)	0.0137 (9)	0.0000 (9)
O13	0.0213 (6)	0.0281 (7)	0.0191 (6)	0.0014 (5)	0.0060 (5)	0.0050 (5)
C14	0.0254 (9)	0.0219 (8)	0.0173 (8)	−0.0003 (7)	0.0065 (7)	−0.0003 (7)
O15	0.0263 (7)	0.0366 (8)	0.0277 (7)	0.0003 (6)	0.0110 (6)	0.0078 (6)
C16	0.0236 (9)	0.0240 (9)	0.0195 (8)	0.0006 (7)	0.0064 (7)	0.0031 (7)
O17	0.0333 (7)	0.0290 (7)	0.0249 (7)	0.0050 (6)	0.0125 (6)	0.0091 (5)
C18	0.0265 (9)	0.0334 (10)	0.0170 (8)	−0.0026 (8)	0.0074 (7)	0.0008 (7)
C19	0.0270 (10)	0.0471 (12)	0.0258 (10)	−0.0005 (9)	0.0060 (8)	−0.0004 (9)
C20	0.0301 (11)	0.0685 (16)	0.0255 (11)	−0.0128 (11)	0.0042 (8)	−0.0008 (11)
C21	0.0498 (14)	0.0542 (15)	0.0265 (11)	−0.0224 (11)	0.0095 (10)	−0.0093 (10)
C22	0.0534 (14)	0.0398 (12)	0.0332 (12)	−0.0093 (10)	0.0131 (10)	−0.0120 (10)
C23	0.0343 (11)	0.0355 (11)	0.0261 (10)	−0.0017 (8)	0.0076 (8)	−0.0054 (8)
C24	0.0198 (8)	0.0273 (9)	0.0182 (8)	0.0018 (7)	0.0033 (6)	0.0021 (7)
C25	0.0246 (9)	0.0283 (10)	0.0263 (9)	0.0003 (7)	0.0054 (7)	0.0010 (8)
C26	0.0305 (10)	0.0319 (10)	0.0291 (10)	0.0043 (8)	0.0046 (8)	−0.0052 (8)
C27	0.0262 (9)	0.0446 (12)	0.0234 (9)	0.0069 (8)	0.0070 (7)	−0.0033 (8)
C28	0.0257 (9)	0.0411 (11)	0.0236 (9)	0.0011 (8)	0.0082 (8)	0.0043 (8)
C29	0.0267 (9)	0.0281 (9)	0.0221 (9)	0.0000 (7)	0.0076 (7)	0.0012 (7)
C30	0.0205 (8)	0.0271 (9)	0.0220 (9)	0.0021 (7)	0.0051 (7)	0.0020 (7)
C31	0.0270 (9)	0.0217 (8)	0.0227 (9)	0.0024 (7)	0.0060 (7)	−0.0012 (7)
C32	0.0254 (9)	0.0209 (8)	0.0217 (9)	−0.0025 (7)	0.0057 (7)	0.0009 (7)
N33	0.0221 (7)	0.0250 (8)	0.0194 (7)	0.0007 (6)	0.0059 (6)	0.0011 (6)
C34	0.0272 (9)	0.0206 (8)	0.0245 (9)	−0.0005 (7)	0.0046 (7)	−0.0013 (7)
C35	0.0243 (9)	0.0241 (9)	0.0273 (10)	−0.0021 (7)	0.0045 (7)	0.0044 (7)
C36	0.0287 (9)	0.0285 (10)	0.0267 (10)	0.0059 (8)	0.0074 (8)	−0.0015 (8)
C37	0.0227 (9)	0.0346 (10)	0.0271 (9)	−0.0007 (7)	0.0089 (7)	0.0016 (8)
C38	0.0315 (10)	0.0387 (11)	0.0195 (9)	0.0018 (8)	0.0086 (7)	−0.0007 (8)
C39	0.0419 (12)	0.0556 (14)	0.0302 (11)	0.0121 (11)	0.0129 (9)	0.0163 (10)
C40	0.0418 (13)	0.0614 (16)	0.0380 (12)	0.0198 (12)	0.0154 (10)	0.0189 (12)
C41	0.0216 (9)	0.0403 (11)	0.0264 (10)	0.0041 (8)	0.0066 (7)	0.0019 (8)
O43	0.0402 (9)	0.0682 (12)	0.0449 (10)	0.0033 (8)	0.0151 (8)	0.0203 (9)

Geometric parameters (Å, º)

S1—O2	1.4505 (17)	C26—H261	0.951
S1—O3	1.4302 (17)	C27—C28	1.385 (3)
S1—N4	1.6000 (17)	C27—H271	0.949
S1—C8	1.761 (2)	C28—C29	1.384 (3)
N4—C5	1.354 (2)	C28—H281	0.930
C5—O6	1.237 (2)	C29—H291	0.941
C5—C7	1.498 (3)	C30—C31	1.526 (3)
C7—C8	1.380 (3)	C30—C35	1.527 (3)
C7—C12	1.393 (3)	C30—H301	0.983
C8—C9	1.384 (3)	C31—C32	1.524 (3)
C9—C10	1.391 (3)	C31—H312	0.961
C9—H91	0.978	C31—H311	0.966
C10—C11	1.376 (3)	C32—N33	1.529 (2)
C10—H101	0.929	C32—C37	1.535 (3)
C11—C12	1.392 (3)	C32—H321	0.963
C11—H111	0.962	N33—C34	1.521 (2)
C12—H121	0.964	N33—C38	1.520 (2)
O13—C14	1.336 (2)	N33—C41	1.517 (2)
O13—C30	1.471 (2)	C34—C35	1.526 (3)
C14—O15	1.205 (2)	C34—C36	1.528 (3)
C14—C16	1.544 (2)	C34—H341	0.990
C16—O17	1.418 (2)	C35—H351	0.970
C16—C18	1.529 (3)	C35—H352	0.970
C16—C24	1.529 (3)	C36—C37	1.548 (3)
O17—H171	0.805	C36—H361	0.983
C18—C19	1.397 (3)	C36—H362	0.963
C18—C23	1.384 (3)	C37—H371	0.963
C19—C20	1.387 (3)	C37—H372	0.973
C19—H191	0.952	C38—C39	1.507 (3)
C20—C21	1.381 (4)	C38—H382	0.970
C20—H201	0.930	C38—H381	0.973
C21—C22	1.374 (4)	C39—C40	1.515 (3)
C21—H211	0.947	C39—H392	0.985
C22—C23	1.396 (3)	C39—H391	0.952
C22—H221	0.948	C40—C41	1.506 (3)
C23—H231	0.936	C40—H402	0.981
C24—C25	1.392 (3)	C40—H401	0.972
C24—C29	1.389 (3)	C41—H412	0.976
C25—C26	1.389 (3)	C41—H411	0.959
C25—H251	0.934	O43—H431	0.837
C26—C27	1.379 (3)	O43—H432	0.831
O2—S1—O3	114.13 (11)	C28—C29—H291	120.6
O2—S1—N4	110.69 (10)	O13—C30—C31	107.64 (14)
O3—S1—N4	112.02 (10)	O13—C30—C35	109.03 (15)
O2—S1—C8	109.15 (10)	C31—C30—C35	113.11 (15)
O3—S1—C8	112.37 (10)	O13—C30—H301	108.1
N4—S1—C8	97.23 (9)	C31—C30—H301	109.2
S1—N4—C5	111.86 (14)	C35—C30—H301	109.6
N4—C5—O6	123.71 (18)	C30—C31—C32	114.27 (15)
N4—C5—C7	112.77 (17)	C30—C31—H312	110.1
O6—C5—C7	123.50 (18)	C32—C31—H312	108.5
C5—C7—C8	111.30 (17)	C30—C31—H311	108.3
C5—C7—C12	128.75 (19)	C32—C31—H311	108.4
C8—C7—C12	119.95 (19)	H312—C31—H311	107.1
S1—C8—C7	106.79 (15)	C31—C32—N33	110.25 (14)
S1—C8—C9	130.19 (17)	C31—C32—C37	111.75 (15)
C7—C8—C9	123.0 (2)	N33—C32—C37	101.99 (14)
C8—C9—C10	116.5 (2)	C31—C32—H321	110.1
C8—C9—H91	122.4	N33—C32—H321	109.8
C10—C9—H91	121.1	C37—C32—H321	112.6
C9—C10—C11	121.5 (2)	C32—N33—C34	100.36 (13)
C9—C10—H101	116.9	C32—N33—C38	110.23 (14)
C11—C10—H101	121.6	C34—N33—C38	112.52 (15)
C10—C11—C12	121.5 (2)	C32—N33—C41	117.67 (15)
C10—C11—H111	117.6	C34—N33—C41	113.96 (15)
C12—C11—H111	120.7	C38—N33—C41	102.49 (14)
C7—C12—C11	117.6 (2)	N33—C34—C35	108.78 (15)
C7—C12—H121	121.0	N33—C34—C36	101.82 (15)
C11—C12—H121	121.5	C35—C34—C36	114.19 (16)
C14—O13—C30	115.95 (14)	N33—C34—H341	108.8
O13—C14—O15	124.57 (17)	C35—C34—H341	110.8
O13—C14—C16	112.61 (15)	C36—C34—H341	112.0
O15—C14—C16	122.82 (16)	C30—C35—C34	114.79 (15)
C14—C16—O17	108.17 (14)	C30—C35—H351	107.7
C14—C16—C18	110.31 (15)	C34—C35—H351	108.8
O17—C16—C18	109.94 (15)	C30—C35—H352	110.6
C14—C16—C24	108.10 (14)	C34—C35—H352	107.2
O17—C16—C24	107.22 (15)	H351—C35—H352	107.6
C18—C16—C24	112.93 (15)	C34—C36—C37	104.87 (15)
C16—O17—H171	112.7	C34—C36—H361	109.3
C16—C18—C19	118.12 (18)	C37—C36—H361	111.2
C16—C18—C23	123.45 (17)	C34—C36—H362	110.4
C19—C18—C23	118.39 (19)	C37—C36—H362	110.5
C18—C19—C20	120.6 (2)	H361—C36—H362	110.4
C18—C19—H191	119.0	C32—C37—C36	105.16 (15)
C20—C19—H191	120.5	C32—C37—H371	109.4
C19—C20—C21	120.5 (2)	C36—C37—H371	110.0
C19—C20—H201	119.4	C32—C37—H372	111.1
C21—C20—H201	120.2	C36—C37—H372	112.4
C20—C21—C22	119.5 (2)	H371—C37—H372	108.7
C20—C21—H211	119.7	N33—C38—C39	104.35 (16)
C22—C21—H211	120.8	N33—C38—H382	109.8
C21—C22—C23	120.4 (2)	C39—C38—H382	113.7
C21—C22—H221	119.8	N33—C38—H381	107.7
C23—C22—H221	119.9	C39—C38—H381	111.4
C22—C23—C18	120.7 (2)	H382—C38—H381	109.6
C22—C23—H231	119.0	C38—C39—C40	105.20 (18)
C18—C23—H231	120.2	C38—C39—H392	109.7
C16—C24—C25	120.27 (17)	C40—C39—H392	110.7
C16—C24—C29	120.70 (17)	C38—C39—H391	109.8
C25—C24—C29	118.90 (17)	C40—C39—H391	112.1
C24—C25—C26	120.01 (19)	H392—C39—H391	109.3
C24—C25—H251	119.6	C39—C40—C41	106.88 (18)
C26—C25—H251	120.3	C39—C40—H402	110.4
C25—C26—C27	120.6 (2)	C41—C40—H402	111.8
C25—C26—H261	119.7	C39—C40—H401	109.9
C27—C26—H261	119.7	C41—C40—H401	108.4
C26—C27—C28	119.61 (19)	H402—C40—H401	109.4
C26—C27—H271	119.9	N33—C41—C40	106.36 (16)
C28—C27—H271	120.5	N33—C41—H412	110.0
C27—C28—C29	119.98 (19)	C40—C41—H412	113.6
C27—C28—H281	119.7	N33—C41—H411	106.5
C29—C28—H281	120.3	C40—C41—H411	109.5
C24—C29—C28	120.83 (19)	H412—C41—H411	110.6
C24—C29—H291	118.5	H431—O43—H432	104.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H121···O17^i	0.96	2.50	3.388 (3)	152 (1)
C32—H321···O6	0.96	2.60	3.407 (3)	142 (1)
C34—H341···O6^ii	0.99	2.45	3.382 (3)	156 (1)
C41—H412···O2^iii	0.98	2.45	3.348 (3)	152 (1)
O17—H171···O6^iv	0.81	2.01	2.783 (3)	163 (1)
O43—H431···O3	0.84	2.16	2.961 (3)	162 (1)
O43—H432···N4^iii	0.83	2.19	3.017 (3)	172 (1)

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