Four oxo­indole-linked α-alk­oxy-β-amino acid derivatives

Four structures of oxoindolyl α-hy­droxy-β-amino acid derivatives, namely, methyl 2-{3-[(tert-but­oxy­carbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-meth­oxy-2-phenyl­acetate, C₂₄H₂₈N₂O₆, (I), methyl 2-{3-[(tert-but­oxy­carbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-eth­oxy-2-phenyl­acetate, C₂₅H₃₀N₂O₆, (II), methyl 2-{3-[(tert-but­oxy­carbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-[(4-meth­oxy­ben­zyl)­oxy]-2-phenyl­acetate, C₃₁H₃₄N₂O₇, (III), and methyl 2-[(anthracen-9-yl)meth­oxy]-2-{3-[(tert-but­oxy­carbonyl)amino]-1-methyl-2-oxo­indolin-3-yl}-2-phenyl­acetate, C₃₈H₃₆N₂O₆, (IV), have been determined. The diastereo­selec­tivity of the chemical reaction involving α-diazoesters and isatin imines in the presence of benzyl alcohol is confirmed through the relative configuration of the two stereo­genic centres. In esters (I) and (III), the amide group adopts an anti conformation, whereas the conformation is syn in esters (II) and (IV). Nevertheless, the amide group forms intra­molecular N—H...O hydrogen bonds with the ester and ether O atoms in all four structures. The ether-linked substituents are in the extended conformation in all four structures. Ester (II) is dominated by inter­molecular N—H...O hydrogen-bond inter­actions. In contrast, the remaining three structures are sustained by C—H...O hydrogen-bond inter­actions.

Computing details

For all compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(I) Methyl 2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-methoxy-2-phenylacetate

Crystal data

C24H28N2O6	Dx = 1.273 Mg m^−3
Mr = 440.48	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 5688 reflections
a = 16.7030 (13) Å	θ = 2.4–23.0°
b = 8.0515 (6) Å	µ = 0.09 mm^−1
c = 17.0919 (13) Å	T = 294 K
V = 2298.6 (3) Å^3	Needle, colourless
Z = 4	0.18 × 0.08 × 0.07 mm
F(000) = 936

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4489 reflections with I > 2σ(I)
ω scans	Rint = 0.037
Absorption correction: multi-scan (SADABS; Bruker, 2001)	θmax = 26.2°, θmin = 2.4°
Tmin = 0.93, Tmax = 0.97	h = −20→20
23155 measured reflections	k = −10→10
4626 independent reflections	l = −21→21

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.074	w = 1/[σ^2(Fo^2) + (0.0598P)^2 + 1.288P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.167	(Δ/σ)max < 0.001
S = 1.31	Δρmax = 0.31 e Å^−3
4626 reflections	Δρmin = −0.21 e Å^−3
292 parameters	Absolute structure: Flack x parameter determined using 1729 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.6 (4)

Special details

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.

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

	x	y	z	Uiso*/Ueq
C1	0.0724 (3)	0.2292 (5)	0.1482 (3)	0.0301 (10)
C2	0.0686 (3)	0.3276 (6)	0.0733 (3)	0.0334 (10)
C3	0.1199 (3)	0.3419 (6)	0.0110 (3)	0.0433 (13)
H3	0.1673	0.2812	0.0097	0.052*
C4	0.1003 (4)	0.4480 (7)	−0.0500 (3)	0.0511 (15)
H4	0.1351	0.4595	−0.0921	0.061*
C5	0.0298 (5)	0.5361 (7)	−0.0487 (4)	0.0592 (18)
H5	0.0168	0.6034	−0.0910	0.071*
C6	−0.0221 (4)	0.5271 (8)	0.0140 (4)	0.0542 (16)
H6	−0.0693	0.5885	0.0152	0.065*
C7	−0.0011 (3)	0.4230 (6)	0.0748 (3)	0.0411 (12)
C8	0.0001 (3)	0.2991 (6)	0.1943 (3)	0.0354 (11)
C9	0.0584 (3)	0.0379 (6)	0.1322 (3)	0.0334 (11)
C10	−0.0183 (3)	0.0127 (6)	0.0832 (3)	0.0347 (11)
C11	−0.0111 (4)	−0.0204 (7)	0.0041 (3)	0.0434 (13)
H11	0.0393	−0.0307	−0.0185	0.052*
C12	−0.0794 (4)	−0.0383 (8)	−0.0417 (4)	0.0580 (17)
H12	−0.0741	−0.0614	−0.0947	0.070*
C13	−0.1541 (4)	−0.0227 (9)	−0.0103 (4)	0.0643 (19)
H13	−0.1993	−0.0358	−0.0415	0.077*
C14	−0.1618 (4)	0.0126 (9)	0.0680 (4)	0.0586 (17)
H14	−0.2124	0.0247	0.0900	0.070*
C15	−0.0944 (4)	0.0302 (7)	0.1138 (3)	0.0450 (13)
H15	−0.1004	0.0545	0.1667	0.054*
C16	0.1638 (3)	0.3923 (6)	0.2264 (3)	0.0321 (10)
C17	0.2538 (3)	0.4990 (7)	0.3286 (3)	0.0430 (13)
C18	0.3287 (4)	0.4238 (10)	0.3630 (4)	0.0619 (18)
H18A	0.3494	0.4957	0.4030	0.093*
H18B	0.3163	0.3174	0.3852	0.093*
H18C	0.3681	0.4105	0.3225	0.093*
C19	0.1888 (4)	0.5119 (11)	0.3889 (4)	0.073 (2)
H19A	0.2033	0.5936	0.4273	0.109*
H19B	0.1396	0.5441	0.3640	0.109*
H19C	0.1818	0.4062	0.4140	0.109*
C20	0.2714 (4)	0.6617 (8)	0.2894 (4)	0.0618 (18)
H20A	0.2858	0.7426	0.3282	0.093*
H20B	0.3149	0.6478	0.2533	0.093*
H20C	0.2247	0.6989	0.2617	0.093*
C21	0.0595 (3)	−0.0577 (6)	0.2116 (3)	0.0354 (11)
C22	−0.0051 (4)	−0.2414 (8)	0.2971 (4)	0.0507 (14)
H22A	−0.0546	−0.3014	0.3015	0.076*
H22B	0.0388	−0.3184	0.2966	0.076*
H22C	0.0004	−0.1676	0.3408	0.076*
C23	−0.1184 (4)	0.4730 (10)	0.1658 (6)	0.0707 (19)
H23A	−0.1371	0.5395	0.1229	0.106*
H23B	−0.1564	0.3865	0.1764	0.106*
H23C	−0.1124	0.5415	0.2114	0.106*
C24	0.1432 (4)	−0.1835 (7)	0.0847 (4)	0.0497 (14)
H24A	0.1915	−0.2017	0.0554	0.075*
H24B	0.1490	−0.2293	0.1362	0.075*
H24C	0.0992	−0.2364	0.0586	0.075*
N1	−0.0412 (3)	0.3993 (6)	0.1456 (3)	0.0439 (11)
N2	0.1479 (3)	0.2492 (5)	0.1899 (2)	0.0365 (10)
H1N	0.169 (3)	0.161 (8)	0.207 (4)	0.044*
O1	−0.0174 (2)	0.2601 (5)	0.2609 (2)	0.0526 (10)
O2	0.1283 (2)	−0.0104 (4)	0.0903 (2)	0.0375 (8)
O3	0.1172 (2)	−0.0553 (5)	0.2537 (2)	0.0498 (10)
O4	−0.0050 (2)	−0.1462 (5)	0.2251 (2)	0.0456 (9)
O5	0.1257 (2)	0.5168 (4)	0.2199 (2)	0.0450 (9)
O6	0.2314 (2)	0.3733 (4)	0.2696 (2)	0.0456 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.032 (2)	0.026 (2)	0.032 (2)	−0.0042 (18)	−0.0030 (19)	−0.003 (2)
C2	0.039 (3)	0.025 (2)	0.035 (2)	−0.0110 (19)	−0.007 (2)	−0.004 (2)
C3	0.051 (3)	0.032 (3)	0.046 (3)	−0.012 (2)	0.002 (3)	−0.010 (2)
C4	0.080 (4)	0.040 (3)	0.034 (3)	−0.019 (3)	0.002 (3)	−0.001 (2)
C5	0.096 (5)	0.039 (3)	0.043 (3)	−0.013 (3)	−0.027 (4)	0.005 (3)
C6	0.061 (4)	0.044 (3)	0.057 (4)	−0.002 (3)	−0.027 (3)	−0.003 (3)
C7	0.048 (3)	0.031 (2)	0.044 (3)	−0.006 (2)	−0.018 (3)	−0.008 (2)
C8	0.032 (2)	0.036 (3)	0.038 (3)	−0.009 (2)	−0.002 (2)	−0.009 (2)
C9	0.034 (3)	0.028 (2)	0.039 (3)	−0.0057 (19)	0.001 (2)	−0.001 (2)
C10	0.044 (3)	0.027 (2)	0.033 (2)	−0.005 (2)	−0.005 (2)	0.003 (2)
C11	0.052 (3)	0.039 (3)	0.039 (3)	−0.012 (2)	−0.002 (3)	0.002 (2)
C12	0.080 (5)	0.058 (4)	0.036 (3)	−0.015 (3)	−0.014 (3)	0.001 (3)
C13	0.063 (4)	0.062 (4)	0.068 (5)	−0.015 (3)	−0.032 (4)	0.006 (3)
C14	0.039 (3)	0.072 (4)	0.065 (4)	−0.010 (3)	−0.009 (3)	0.007 (3)
C15	0.047 (3)	0.047 (3)	0.040 (3)	−0.005 (3)	0.000 (2)	0.002 (2)
C16	0.035 (2)	0.027 (2)	0.034 (2)	0.0030 (19)	−0.007 (2)	0.002 (2)
C17	0.033 (3)	0.060 (3)	0.036 (3)	−0.006 (2)	−0.005 (2)	−0.016 (3)
C18	0.043 (3)	0.082 (5)	0.060 (4)	0.008 (3)	−0.016 (3)	−0.012 (4)
C19	0.053 (4)	0.110 (6)	0.055 (4)	0.004 (4)	0.002 (3)	−0.011 (4)
C20	0.054 (4)	0.055 (4)	0.076 (4)	−0.014 (3)	−0.016 (3)	−0.007 (3)
C21	0.042 (3)	0.036 (2)	0.029 (2)	0.006 (2)	0.001 (2)	−0.005 (2)
C22	0.055 (3)	0.048 (3)	0.048 (3)	0.002 (3)	0.010 (3)	0.016 (3)
C23	0.051 (4)	0.074 (5)	0.087 (5)	0.018 (3)	−0.004 (4)	−0.013 (4)
C24	0.062 (4)	0.040 (3)	0.047 (3)	−0.001 (3)	0.005 (3)	−0.012 (3)
N1	0.037 (2)	0.043 (3)	0.051 (3)	0.005 (2)	−0.005 (2)	−0.009 (2)
N2	0.035 (2)	0.032 (2)	0.042 (2)	0.0044 (18)	−0.0086 (19)	−0.0004 (19)
O1	0.052 (2)	0.063 (3)	0.042 (2)	−0.0049 (19)	0.0092 (19)	−0.008 (2)
O2	0.0408 (19)	0.0326 (18)	0.0391 (19)	−0.0002 (14)	0.0029 (16)	−0.0021 (15)
O3	0.056 (2)	0.052 (2)	0.041 (2)	−0.0042 (19)	−0.0134 (19)	0.0118 (18)
O4	0.045 (2)	0.050 (2)	0.0417 (19)	−0.0051 (17)	0.0029 (17)	0.0132 (19)
O5	0.045 (2)	0.0329 (19)	0.057 (2)	0.0011 (16)	−0.0176 (18)	−0.0062 (18)
O6	0.0403 (19)	0.044 (2)	0.053 (2)	0.0039 (16)	−0.0143 (18)	−0.0088 (18)

Geometric parameters (Å, º)

C1—N2	1.457 (6)	C16—O5	1.193 (5)
C1—C2	1.507 (7)	C16—N2	1.336 (6)
C1—C8	1.548 (7)	C16—O6	1.359 (6)
C1—C9	1.582 (6)	C17—O6	1.478 (6)
C2—C3	1.372 (7)	C17—C19	1.500 (8)
C2—C7	1.395 (7)	C17—C20	1.501 (9)
C3—C4	1.387 (8)	C17—C18	1.509 (8)
C3—H3	0.9300	C18—H18A	0.9600
C4—C5	1.375 (10)	C18—H18B	0.9600
C4—H4	0.9300	C18—H18C	0.9600
C5—C6	1.380 (10)	C19—H19A	0.9600
C5—H5	0.9300	C19—H19B	0.9600
C6—C7	1.380 (8)	C19—H19C	0.9600
C6—H6	0.9300	C20—H20A	0.9600
C7—N1	1.398 (8)	C20—H20B	0.9600
C8—O1	1.216 (6)	C20—H20C	0.9600
C8—N1	1.349 (7)	C21—O3	1.202 (6)
C9—O2	1.423 (6)	C21—O4	1.312 (6)
C9—C10	1.544 (7)	C22—O4	1.449 (7)
C9—C21	1.560 (7)	C22—H22A	0.9600
C10—C15	1.382 (8)	C22—H22B	0.9600
C10—C11	1.384 (8)	C22—H22C	0.9600
C11—C12	1.391 (8)	C23—N1	1.460 (7)
C11—H11	0.9300	C23—H23A	0.9600
C12—C13	1.363 (10)	C23—H23B	0.9600
C12—H12	0.9300	C23—H23C	0.9600
C13—C14	1.373 (10)	C24—O2	1.419 (6)
C13—H13	0.9300	C24—H24A	0.9600
C14—C15	1.378 (8)	C24—H24B	0.9600
C14—H14	0.9300	C24—H24C	0.9600
C15—H15	0.9300	N2—H1N	0.85 (6)
N2—C1—C2	113.2 (4)	O6—C17—C19	109.5 (5)
N2—C1—C8	112.7 (4)	O6—C17—C20	110.0 (5)
C2—C1—C8	102.0 (4)	C19—C17—C20	112.8 (6)
N2—C1—C9	108.7 (4)	O6—C17—C18	101.5 (5)
C2—C1—C9	111.0 (4)	C19—C17—C18	111.2 (5)
C8—C1—C9	109.1 (4)	C20—C17—C18	111.2 (5)
C3—C2—C7	119.3 (5)	C17—C18—H18A	109.5
C3—C2—C1	132.6 (5)	C17—C18—H18B	109.5
C7—C2—C1	108.1 (4)	H18A—C18—H18B	109.5
C2—C3—C4	119.2 (5)	C17—C18—H18C	109.5
C2—C3—H3	120.4	H18A—C18—H18C	109.5
C4—C3—H3	120.4	H18B—C18—H18C	109.5
C5—C4—C3	120.5 (6)	C17—C19—H19A	109.5
C5—C4—H4	119.7	C17—C19—H19B	109.5
C3—C4—H4	119.7	H19A—C19—H19B	109.5
C4—C5—C6	121.5 (6)	C17—C19—H19C	109.5
C4—C5—H5	119.2	H19A—C19—H19C	109.5
C6—C5—H5	119.2	H19B—C19—H19C	109.5
C7—C6—C5	117.2 (6)	C17—C20—H20A	109.5
C7—C6—H6	121.4	C17—C20—H20B	109.5
C5—C6—H6	121.4	H20A—C20—H20B	109.5
C6—C7—C2	122.2 (6)	C17—C20—H20C	109.5
C6—C7—N1	127.8 (5)	H20A—C20—H20C	109.5
C2—C7—N1	109.9 (5)	H20B—C20—H20C	109.5
O1—C8—N1	127.4 (5)	O3—C21—O4	124.1 (5)
O1—C8—C1	124.8 (5)	O3—C21—C9	121.4 (5)
N1—C8—C1	107.7 (4)	O4—C21—C9	114.3 (4)
O2—C9—C10	111.8 (4)	O4—C22—H22A	109.5
O2—C9—C21	107.1 (4)	O4—C22—H22B	109.5
C10—C9—C21	114.6 (4)	H22A—C22—H22B	109.5
O2—C9—C1	103.4 (4)	O4—C22—H22C	109.5
C10—C9—C1	110.1 (4)	H22A—C22—H22C	109.5
C21—C9—C1	109.2 (4)	H22B—C22—H22C	109.5
C15—C10—C11	118.0 (5)	N1—C23—H23A	109.5
C15—C10—C9	123.0 (5)	N1—C23—H23B	109.5
C11—C10—C9	118.9 (5)	H23A—C23—H23B	109.5
C10—C11—C12	119.8 (6)	N1—C23—H23C	109.5
C10—C11—H11	120.1	H23A—C23—H23C	109.5
C12—C11—H11	120.1	H23B—C23—H23C	109.5
C13—C12—C11	121.3 (6)	O2—C24—H24A	109.5
C13—C12—H12	119.3	O2—C24—H24B	109.5
C11—C12—H12	119.3	H24A—C24—H24B	109.5
C12—C13—C14	119.2 (6)	O2—C24—H24C	109.5
C12—C13—H13	120.4	H24A—C24—H24C	109.5
C14—C13—H13	120.4	H24B—C24—H24C	109.5
C13—C14—C15	119.9 (6)	C8—N1—C7	111.7 (4)
C13—C14—H14	120.1	C8—N1—C23	123.3 (6)
C15—C14—H14	120.1	C7—N1—C23	124.9 (6)
C14—C15—C10	121.7 (6)	C16—N2—C1	119.6 (4)
C14—C15—H15	119.1	C16—N2—H1N	119 (4)
C10—C15—H15	119.1	C1—N2—H1N	116 (4)
O5—C16—N2	125.2 (4)	C24—O2—C9	116.5 (4)
O5—C16—O6	126.1 (4)	C21—O4—C22	116.0 (5)
N2—C16—O6	108.8 (4)	C16—O6—C17	120.3 (4)
N2—C1—C2—C3	49.7 (7)	C15—C10—C11—C12	−1.3 (8)
C8—C1—C2—C3	171.1 (5)	C9—C10—C11—C12	−178.0 (5)
C9—C1—C2—C3	−72.8 (6)	C10—C11—C12—C13	0.5 (9)
N2—C1—C2—C7	−127.4 (4)	C11—C12—C13—C14	0.5 (10)
C8—C1—C2—C7	−6.0 (5)	C12—C13—C14—C15	−0.6 (10)
C9—C1—C2—C7	110.1 (4)	C13—C14—C15—C10	−0.2 (10)
C7—C2—C3—C4	−1.6 (7)	C11—C10—C15—C14	1.2 (8)
C1—C2—C3—C4	−178.4 (5)	C9—C10—C15—C14	177.7 (5)
C2—C3—C4—C5	−0.9 (8)	O2—C9—C21—O3	51.8 (6)
C3—C4—C5—C6	2.4 (9)	C10—C9—C21—O3	176.4 (5)
C4—C5—C6—C7	−1.3 (9)	C1—C9—C21—O3	−59.5 (6)
C5—C6—C7—C2	−1.2 (8)	O2—C9—C21—O4	−124.4 (4)
C5—C6—C7—N1	176.5 (5)	C10—C9—C21—O4	0.2 (6)
C3—C2—C7—C6	2.7 (7)	C1—C9—C21—O4	124.3 (4)
C1—C2—C7—C6	−179.8 (5)	O1—C8—N1—C7	177.0 (5)
C3—C2—C7—N1	−175.4 (4)	C1—C8—N1—C7	−7.3 (5)
C1—C2—C7—N1	2.2 (5)	O1—C8—N1—C23	−2.8 (9)
N2—C1—C8—O1	−54.5 (6)	C1—C8—N1—C23	172.9 (5)
C2—C1—C8—O1	−176.2 (5)	C6—C7—N1—C8	−174.5 (5)
C9—C1—C8—O1	66.3 (6)	C2—C7—N1—C8	3.4 (6)
N2—C1—C8—N1	129.7 (4)	C6—C7—N1—C23	5.3 (9)
C2—C1—C8—N1	8.0 (5)	C2—C7—N1—C23	−176.8 (5)
C9—C1—C8—N1	−109.5 (4)	O5—C16—N2—C1	−10.3 (8)
N2—C1—C9—O2	−56.6 (5)	O6—C16—N2—C1	171.6 (4)
C2—C1—C9—O2	68.6 (5)	C2—C1—N2—C16	72.3 (5)
C8—C1—C9—O2	−179.8 (4)	C8—C1—N2—C16	−42.9 (6)
N2—C1—C9—C10	−176.2 (4)	C9—C1—N2—C16	−163.9 (4)
C2—C1—C9—C10	−51.0 (5)	C10—C9—O2—C24	−77.1 (5)
C8—C1—C9—C10	60.6 (5)	C21—C9—O2—C24	49.3 (5)
N2—C1—C9—C21	57.1 (5)	C1—C9—O2—C24	164.5 (4)
C2—C1—C9—C21	−177.7 (4)	O3—C21—O4—C22	1.9 (8)
C8—C1—C9—C21	−66.1 (5)	C9—C21—O4—C22	177.9 (4)
O2—C9—C10—C15	171.6 (5)	O5—C16—O6—C17	14.7 (8)
C21—C9—C10—C15	49.5 (6)	N2—C16—O6—C17	−167.2 (4)
C1—C9—C10—C15	−74.1 (6)	C19—C17—O6—C16	60.2 (7)
O2—C9—C10—C11	−11.9 (6)	C20—C17—O6—C16	−64.4 (6)
C21—C9—C10—C11	−134.0 (5)	C18—C17—O6—C16	177.8 (5)
C1—C9—C10—C11	102.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O3	0.85 (6)	2.10 (6)	2.732 (6)	132 (5)
C11—H11···O2	0.93	2.39	2.756 (7)	104
C15—H15···O4	0.93	2.48	2.805 (7)	101
C22—H22B···O5^i	0.96	2.36	3.209 (8)	147
C24—H24B···O5^i	0.96	2.53	3.355 (7)	145

Symmetry code: (i) x, y−1, z.

(II) Methyl 2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-ethoxy-2-phenylacetate

Crystal data

C25H30N2O6	Z = 4
Mr = 454.51	F(000) = 968
Triclinic, P1	Dx = 1.248 Mg m^−3
a = 11.2274 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.3892 (17) Å	Cell parameters from 4954 reflections
c = 16.849 (2) Å	θ = 2.3–22.2°
α = 91.475 (2)°	µ = 0.09 mm^−1
β = 92.646 (2)°	T = 294 K
γ = 106.889 (2)°	Block, colourless
V = 2419.0 (5) Å^3	0.19 × 0.17 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	6677 reflections with I > 2σ(I)
ω scans	Rint = 0.044
Absorption correction: multi-scan (SADABS; Bruker, 2001)	θmax = 28.4°, θmin = 1.2°
Tmin = 0.96, Tmax = 0.99	h = −14→14
28011 measured reflections	k = −17→17
11329 independent reflections	l = −22→22

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.154	w = 1/[σ^2(Fo^2) + (0.0596P)^2 + 0.4978P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
11329 reflections	Δρmax = 0.25 e Å^−3
615 parameters	Δρmin = −0.20 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
C1A	0.81031 (17)	0.27628 (15)	0.57648 (11)	0.0329 (4)
C2A	0.83654 (18)	0.26739 (16)	0.66429 (12)	0.0358 (5)
C3A	0.8623 (2)	0.34097 (19)	0.72534 (14)	0.0491 (6)
H3A	0.8661	0.4099	0.7158	0.059*
C4A	0.8828 (2)	0.3109 (2)	0.80199 (15)	0.0633 (7)
H4A	0.8986	0.3596	0.8444	0.076*
C5A	0.8799 (2)	0.2095 (3)	0.81498 (16)	0.0685 (8)
H5A	0.8945	0.1906	0.8664	0.082*
C6A	0.8558 (2)	0.1352 (2)	0.75383 (16)	0.0593 (7)
H6A	0.8544	0.0667	0.7631	0.071*
C7A	0.83383 (19)	0.16533 (17)	0.67854 (13)	0.0411 (5)
C8A	0.80205 (19)	0.16542 (16)	0.54380 (14)	0.0395 (5)
C9A	0.67793 (18)	0.29320 (15)	0.56056 (12)	0.0352 (5)
C10A	0.58240 (18)	0.21638 (16)	0.60909 (12)	0.0376 (5)
C11A	0.5564 (2)	0.24880 (18)	0.68350 (13)	0.0464 (6)
H11A	0.5913	0.3180	0.7011	0.056*
C12A	0.4791 (2)	0.1794 (2)	0.73191 (15)	0.0596 (7)
H12A	0.4622	0.2021	0.7816	0.072*
C13A	0.4274 (2)	0.0772 (2)	0.70655 (17)	0.0629 (7)
H13A	0.3765	0.0304	0.7394	0.075*
C14A	0.4506 (2)	0.0437 (2)	0.63298 (17)	0.0608 (7)
H14A	0.4146	−0.0255	0.6157	0.073*
C15A	0.5277 (2)	0.11303 (18)	0.58429 (14)	0.0497 (6)
H15A	0.5429	0.0899	0.5343	0.060*
C16A	1.02677 (19)	0.36069 (16)	0.54016 (12)	0.0357 (5)
C17A	1.1687 (2)	0.26045 (19)	0.58291 (15)	0.0535 (6)
C18A	1.2445 (3)	0.3462 (3)	0.64073 (18)	0.0857 (10)
H18A	1.1966	0.3506	0.6857	0.129*
H18B	1.2655	0.4116	0.6149	0.129*
H18C	1.3195	0.3307	0.6583	0.129*
C19A	1.2309 (3)	0.2604 (2)	0.50592 (17)	0.0700 (8)
H19A	1.2511	0.3290	0.4851	0.105*
H19B	1.1756	0.2114	0.4684	0.105*
H19C	1.3059	0.2407	0.5150	0.105*
C20A	1.1399 (3)	0.1545 (3)	0.6186 (2)	0.1050 (13)
H20A	1.0826	0.1038	0.5831	0.158*
H20B	1.1032	0.1569	0.6686	0.158*
H20C	1.2155	0.1354	0.6266	0.158*
C21A	0.6370 (2)	0.28208 (17)	0.47025 (13)	0.0413 (5)
C22A	0.6982 (3)	0.3388 (2)	0.34359 (14)	0.0706 (8)
H22A	0.6263	0.3614	0.3304	0.106*
H22B	0.6835	0.2679	0.3244	0.106*
H22C	0.7693	0.3829	0.3193	0.106*
C23A	0.7961 (3)	−0.00481 (18)	0.59800 (18)	0.0738 (8)
H23A	0.7970	−0.0236	0.5427	0.111*
H23B	0.7186	−0.0439	0.6184	0.111*
H23C	0.8638	−0.0203	0.6269	0.111*
C24A	0.6015 (2)	0.44484 (18)	0.56553 (14)	0.0464 (6)
H24A	0.5205	0.3929	0.5636	0.056*
H24B	0.6150	0.4736	0.5133	0.056*
C25A	0.6059 (3)	0.5294 (2)	0.62587 (15)	0.0617 (7)
H25A	0.6901	0.5735	0.6343	0.093*
H25B	0.5770	0.4990	0.6750	0.093*
H25C	0.5535	0.5702	0.6072	0.093*
N1A	0.80936 (17)	0.10553 (13)	0.60700 (11)	0.0444 (5)
N2A	0.90606 (15)	0.35737 (14)	0.54078 (10)	0.0373 (4)
H1N	0.888 (2)	0.4100 (17)	0.5239 (13)	0.042 (6)*
O1A	0.78570 (15)	0.13558 (12)	0.47434 (10)	0.0536 (4)
O2A	0.69722 (12)	0.39785 (10)	0.58769 (8)	0.0376 (3)
O3A	0.53926 (16)	0.22841 (15)	0.44248 (10)	0.0691 (5)
O4A	0.72127 (14)	0.34516 (13)	0.42844 (9)	0.0549 (4)
O5A	1.10792 (13)	0.43266 (11)	0.51646 (9)	0.0500 (4)
O6A	1.04341 (13)	0.27273 (11)	0.56832 (10)	0.0495 (4)
C1B	0.94234 (18)	0.71534 (16)	0.91174 (12)	0.0362 (5)
C2B	0.96283 (18)	0.71629 (17)	0.82386 (12)	0.0376 (5)
C3B	0.9396 (2)	0.6369 (2)	0.76736 (14)	0.0526 (6)
H3B	0.9042	0.5681	0.7809	0.063*
C4B	0.9692 (3)	0.6600 (2)	0.68975 (16)	0.0681 (8)
H4B	0.9527	0.6067	0.6507	0.082*
C5B	1.0228 (3)	0.7618 (3)	0.67049 (15)	0.0696 (8)
H5B	1.0424	0.7762	0.6182	0.084*
C6B	1.0485 (2)	0.8435 (2)	0.72679 (14)	0.0566 (7)
H6B	1.0850	0.9122	0.7134	0.068*
C7B	1.01769 (19)	0.81860 (17)	0.80371 (12)	0.0397 (5)
C8B	1.00625 (19)	0.83017 (17)	0.93814 (13)	0.0381 (5)
C9B	0.79901 (18)	0.68990 (16)	0.92675 (12)	0.0371 (5)
C10B	0.74093 (18)	0.76008 (17)	0.87714 (12)	0.0391 (5)
C11B	0.6865 (2)	0.72386 (19)	0.80249 (14)	0.0484 (6)
H11B	0.6836	0.6570	0.7842	0.058*
C12B	0.6362 (2)	0.7858 (2)	0.75452 (16)	0.0612 (7)
H12B	0.6006	0.7610	0.7042	0.073*
C13B	0.6392 (2)	0.8839 (2)	0.78178 (18)	0.0678 (8)
H13B	0.6037	0.9251	0.7504	0.081*
C14B	0.6940 (2)	0.9214 (2)	0.85483 (18)	0.0625 (7)
H14B	0.6965	0.9883	0.8727	0.075*
C15B	0.7461 (2)	0.86067 (19)	0.90248 (15)	0.0508 (6)
H15B	0.7846	0.8874	0.9517	0.061*
C16B	1.1155 (2)	0.65081 (18)	0.96352 (13)	0.0443 (5)
C17B	1.3199 (2)	0.7709 (2)	0.93633 (17)	0.0631 (7)
C18B	1.3685 (3)	0.7915 (3)	1.0218 (2)	0.1233 (15)
H18D	1.3419	0.7281	1.0500	0.185*
H18E	1.3366	0.8436	1.0458	0.185*
H18F	1.4579	0.8159	1.0242	0.185*
C19B	1.3660 (3)	0.6905 (3)	0.8950 (2)	0.1061 (13)
H19D	1.3248	0.6737	0.8431	0.159*
H19E	1.3486	0.6287	0.9254	0.159*
H19F	1.4543	0.7174	0.8900	0.159*
C20B	1.3494 (3)	0.8709 (3)	0.8918 (3)	0.1092 (14)
H20D	1.3119	0.9188	0.9166	0.164*
H20E	1.3170	0.8559	0.8377	0.164*
H20F	1.4382	0.9017	0.8928	0.164*
C21B	0.7743 (2)	0.70021 (19)	1.01626 (14)	0.0472 (6)
C22B	0.7944 (3)	0.6331 (3)	1.14216 (15)	0.0826 (10)
H22D	0.7064	0.6094	1.1490	0.124*
H22E	0.8284	0.7021	1.1659	0.124*
H22F	0.8339	0.5865	1.1673	0.124*
C23B	1.0928 (3)	0.99773 (18)	0.87252 (16)	0.0611 (7)
H23D	1.1781	1.0139	0.8586	0.092*
H23E	1.0894	1.0267	0.9248	0.092*
H23F	1.0469	1.0270	0.8349	0.092*
C24B	0.6265 (2)	0.52966 (19)	0.92108 (15)	0.0550 (6)
H24C	0.5733	0.5750	0.9160	0.066*
H24D	0.6271	0.5082	0.9756	0.066*
C25B	0.5796 (3)	0.4371 (2)	0.86608 (19)	0.0823 (9)
H25D	0.6432	0.4028	0.8610	0.124*
H25E	0.5580	0.4587	0.8149	0.124*
H25F	0.5072	0.3897	0.8867	0.124*
N1B	1.03844 (16)	0.88528 (13)	0.87149 (10)	0.0408 (4)
N2B	0.99319 (17)	0.64226 (15)	0.95415 (11)	0.0439 (5)
H2N	0.942 (2)	0.5854 (18)	0.9688 (13)	0.051 (7)*
O1B	1.02042 (15)	0.86625 (13)	1.00563 (9)	0.0530 (4)
O2B	0.75099 (13)	0.58394 (11)	0.90048 (9)	0.0429 (4)
O3B	0.7172 (2)	0.75280 (18)	1.04338 (11)	0.0899 (7)
O4B	0.81626 (17)	0.63503 (15)	1.05883 (9)	0.0662 (5)
O5B	1.15590 (15)	0.58674 (13)	0.99636 (11)	0.0616 (5)
O6B	1.18365 (13)	0.73856 (12)	0.93265 (10)	0.0554 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0302 (10)	0.0314 (11)	0.0349 (11)	0.0053 (8)	0.0014 (8)	0.0059 (9)
C2A	0.0287 (10)	0.0401 (12)	0.0373 (12)	0.0079 (9)	0.0008 (9)	0.0058 (10)
C3A	0.0441 (13)	0.0537 (15)	0.0474 (14)	0.0120 (11)	−0.0055 (11)	−0.0001 (12)
C4A	0.0605 (17)	0.084 (2)	0.0394 (14)	0.0140 (15)	−0.0078 (12)	−0.0040 (14)
C5A	0.0623 (17)	0.098 (2)	0.0435 (15)	0.0187 (16)	−0.0017 (12)	0.0255 (16)
C6A	0.0560 (16)	0.0610 (16)	0.0614 (17)	0.0149 (13)	0.0071 (13)	0.0309 (14)
C7A	0.0346 (11)	0.0425 (13)	0.0463 (13)	0.0098 (10)	0.0067 (9)	0.0143 (11)
C8A	0.0334 (11)	0.0369 (12)	0.0457 (14)	0.0051 (9)	0.0088 (9)	0.0038 (10)
C9A	0.0307 (11)	0.0340 (11)	0.0385 (11)	0.0062 (9)	−0.0002 (9)	0.0024 (9)
C10A	0.0292 (11)	0.0415 (12)	0.0397 (12)	0.0070 (9)	−0.0012 (9)	0.0034 (10)
C11A	0.0427 (13)	0.0465 (13)	0.0474 (14)	0.0079 (10)	0.0039 (10)	0.0068 (11)
C12A	0.0566 (16)	0.0681 (18)	0.0548 (15)	0.0159 (14)	0.0168 (12)	0.0164 (13)
C13A	0.0498 (15)	0.0623 (18)	0.0720 (19)	0.0054 (13)	0.0141 (13)	0.0284 (15)
C14A	0.0520 (15)	0.0454 (15)	0.0743 (19)	−0.0033 (12)	0.0032 (13)	0.0110 (13)
C15A	0.0415 (13)	0.0479 (14)	0.0520 (14)	0.0009 (11)	0.0014 (11)	0.0015 (11)
C16A	0.0346 (11)	0.0333 (11)	0.0382 (12)	0.0080 (9)	0.0022 (9)	0.0085 (9)
C17A	0.0377 (13)	0.0591 (15)	0.0706 (17)	0.0224 (11)	0.0091 (12)	0.0225 (13)
C18A	0.071 (2)	0.122 (3)	0.070 (2)	0.043 (2)	−0.0175 (16)	−0.0025 (19)
C19A	0.0621 (17)	0.0714 (19)	0.086 (2)	0.0308 (15)	0.0244 (15)	0.0084 (16)
C20A	0.072 (2)	0.100 (2)	0.165 (4)	0.0497 (19)	0.034 (2)	0.085 (2)
C21A	0.0368 (12)	0.0452 (13)	0.0401 (12)	0.0097 (10)	−0.0023 (10)	0.0026 (10)
C22A	0.0633 (17)	0.105 (2)	0.0397 (14)	0.0185 (16)	0.0017 (12)	0.0129 (14)
C23A	0.097 (2)	0.0376 (14)	0.090 (2)	0.0211 (14)	0.0277 (17)	0.0157 (14)
C24A	0.0399 (12)	0.0501 (14)	0.0532 (14)	0.0196 (11)	−0.0024 (10)	0.0063 (11)
C25A	0.0709 (18)	0.0596 (16)	0.0642 (17)	0.0338 (14)	0.0058 (13)	0.0043 (14)
N1A	0.0494 (11)	0.0290 (10)	0.0551 (12)	0.0099 (8)	0.0113 (9)	0.0094 (9)
N2A	0.0314 (10)	0.0330 (10)	0.0473 (11)	0.0078 (8)	0.0035 (8)	0.0144 (8)
O1A	0.0615 (11)	0.0478 (10)	0.0462 (10)	0.0075 (8)	0.0086 (8)	−0.0058 (8)
O2A	0.0338 (8)	0.0350 (8)	0.0436 (8)	0.0100 (6)	−0.0029 (6)	0.0022 (6)
O3A	0.0492 (11)	0.0889 (14)	0.0504 (10)	−0.0073 (10)	−0.0144 (8)	0.0081 (9)
O4A	0.0468 (9)	0.0702 (11)	0.0374 (9)	0.0006 (8)	−0.0033 (7)	0.0128 (8)
O5A	0.0363 (8)	0.0427 (9)	0.0700 (11)	0.0074 (7)	0.0104 (7)	0.0213 (8)
O6A	0.0334 (8)	0.0451 (9)	0.0744 (11)	0.0146 (7)	0.0122 (7)	0.0265 (8)
C1B	0.0349 (11)	0.0424 (12)	0.0343 (11)	0.0151 (9)	0.0039 (9)	0.0084 (9)
C2B	0.0321 (11)	0.0441 (13)	0.0375 (12)	0.0118 (9)	0.0057 (9)	0.0043 (10)
C3B	0.0482 (14)	0.0548 (15)	0.0525 (15)	0.0109 (12)	0.0118 (11)	−0.0052 (12)
C4B	0.0646 (18)	0.087 (2)	0.0478 (16)	0.0154 (16)	0.0106 (13)	−0.0178 (15)
C5B	0.0694 (18)	0.102 (2)	0.0336 (14)	0.0175 (17)	0.0135 (12)	0.0055 (15)
C6B	0.0558 (15)	0.0672 (17)	0.0433 (14)	0.0103 (13)	0.0105 (11)	0.0162 (13)
C7B	0.0350 (11)	0.0491 (13)	0.0366 (12)	0.0140 (10)	0.0032 (9)	0.0067 (10)
C8B	0.0343 (11)	0.0456 (13)	0.0365 (12)	0.0155 (10)	−0.0009 (9)	0.0013 (10)
C9B	0.0349 (11)	0.0426 (13)	0.0353 (11)	0.0127 (9)	0.0046 (9)	0.0050 (9)
C10B	0.0305 (11)	0.0464 (13)	0.0427 (12)	0.0134 (10)	0.0080 (9)	0.0107 (10)
C11B	0.0405 (13)	0.0557 (15)	0.0486 (14)	0.0127 (11)	0.0028 (10)	0.0119 (11)
C12B	0.0461 (15)	0.081 (2)	0.0549 (15)	0.0144 (14)	−0.0003 (12)	0.0269 (14)
C13B	0.0500 (16)	0.079 (2)	0.085 (2)	0.0289 (15)	0.0159 (15)	0.0461 (17)
C14B	0.0609 (17)	0.0528 (16)	0.082 (2)	0.0252 (13)	0.0231 (15)	0.0246 (15)
C15B	0.0486 (14)	0.0538 (15)	0.0540 (15)	0.0193 (12)	0.0102 (11)	0.0101 (12)
C16B	0.0401 (13)	0.0480 (14)	0.0487 (13)	0.0169 (11)	0.0084 (10)	0.0144 (11)
C17B	0.0358 (13)	0.0716 (18)	0.087 (2)	0.0197 (12)	0.0155 (13)	0.0322 (15)
C18B	0.079 (2)	0.144 (4)	0.120 (3)	−0.007 (2)	−0.023 (2)	0.015 (3)
C19B	0.089 (2)	0.106 (3)	0.146 (3)	0.053 (2)	0.068 (2)	0.044 (2)
C20B	0.0514 (18)	0.093 (2)	0.189 (4)	0.0197 (17)	0.039 (2)	0.079 (3)
C21B	0.0417 (13)	0.0598 (15)	0.0434 (13)	0.0182 (12)	0.0096 (10)	0.0093 (12)
C22B	0.0722 (19)	0.138 (3)	0.0409 (15)	0.0322 (19)	0.0101 (13)	0.0298 (17)
C23B	0.0695 (18)	0.0410 (14)	0.0723 (18)	0.0143 (13)	0.0073 (14)	0.0097 (13)
C24B	0.0395 (13)	0.0576 (16)	0.0648 (16)	0.0069 (11)	0.0120 (11)	0.0163 (13)
C25B	0.0655 (19)	0.076 (2)	0.087 (2)	−0.0086 (16)	0.0008 (16)	0.0059 (17)
N1B	0.0413 (10)	0.0378 (10)	0.0430 (11)	0.0103 (8)	0.0043 (8)	0.0090 (8)
N2B	0.0341 (10)	0.0437 (11)	0.0556 (12)	0.0116 (9)	0.0079 (9)	0.0204 (9)
O1B	0.0623 (11)	0.0587 (10)	0.0391 (9)	0.0207 (8)	−0.0030 (8)	−0.0032 (8)
O2B	0.0363 (8)	0.0422 (9)	0.0495 (9)	0.0088 (7)	0.0079 (7)	0.0088 (7)
O3B	0.1243 (18)	0.1163 (18)	0.0620 (12)	0.0788 (16)	0.0448 (12)	0.0268 (12)
O4B	0.0739 (12)	0.0985 (14)	0.0406 (9)	0.0443 (11)	0.0140 (8)	0.0241 (9)
O5B	0.0465 (10)	0.0636 (11)	0.0822 (12)	0.0243 (8)	0.0092 (8)	0.0353 (10)
O6B	0.0343 (8)	0.0566 (10)	0.0796 (12)	0.0163 (7)	0.0124 (8)	0.0311 (9)

Geometric parameters (Å, º)

C1A—N2A	1.453 (2)	C1B—N2B	1.455 (3)
C1A—C2A	1.510 (3)	C1B—C2B	1.509 (3)
C1A—C8A	1.545 (3)	C1B—C8B	1.540 (3)
C1A—C9A	1.579 (3)	C1B—C9B	1.579 (3)
C2A—C3A	1.366 (3)	C2B—C3B	1.367 (3)
C2A—C7A	1.385 (3)	C2B—C7B	1.387 (3)
C3A—C4A	1.391 (3)	C3B—C4B	1.385 (3)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.372 (4)	C4B—C5B	1.375 (4)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.375 (4)	C5B—C6B	1.385 (4)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.374 (3)	C6B—C7B	1.381 (3)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—N1A	1.401 (3)	C7B—N1B	1.399 (3)
C8A—O1A	1.215 (2)	C8B—O1B	1.209 (2)
C8A—N1A	1.363 (3)	C8B—N1B	1.364 (3)
C9A—O2A	1.414 (2)	C9B—O2B	1.414 (2)
C9A—C10A	1.536 (3)	C9B—C10B	1.534 (3)
C9A—C21A	1.560 (3)	C9B—C21B	1.556 (3)
C10A—C15A	1.385 (3)	C10B—C11B	1.384 (3)
C10A—C11A	1.387 (3)	C10B—C15B	1.387 (3)
C11A—C12A	1.385 (3)	C11B—C12B	1.388 (3)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.370 (4)	C12B—C13B	1.371 (4)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.369 (4)	C13B—C14B	1.366 (4)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.386 (3)	C14B—C15B	1.383 (3)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—O5A	1.209 (2)	C16B—O5B	1.214 (2)
C16A—O6A	1.340 (2)	C16B—O6B	1.335 (3)
C16A—N2A	1.344 (3)	C16B—N2B	1.346 (3)
C17A—O6A	1.474 (3)	C17B—O6B	1.461 (3)
C17A—C19A	1.501 (3)	C17B—C19B	1.493 (4)
C17A—C20A	1.507 (3)	C17B—C18B	1.506 (4)
C17A—C18A	1.513 (4)	C17B—C20B	1.511 (4)
C18A—H18A	0.9600	C18B—H18D	0.9600
C18A—H18B	0.9600	C18B—H18E	0.9600
C18A—H18C	0.9600	C18B—H18F	0.9600
C19A—H19A	0.9600	C19B—H19D	0.9600
C19A—H19B	0.9600	C19B—H19E	0.9600
C19A—H19C	0.9600	C19B—H19F	0.9600
C20A—H20A	0.9600	C20B—H20D	0.9600
C20A—H20B	0.9600	C20B—H20E	0.9600
C20A—H20C	0.9600	C20B—H20F	0.9600
C21A—O3A	1.190 (2)	C21B—O3B	1.179 (3)
C21A—O4A	1.316 (3)	C21B—O4B	1.318 (3)
C22A—O4A	1.437 (3)	C22B—O4B	1.436 (3)
C22A—H22A	0.9600	C22B—H22D	0.9600
C22A—H22B	0.9600	C22B—H22E	0.9600
C22A—H22C	0.9600	C22B—H22F	0.9600
C23A—N1A	1.444 (3)	C23B—N1B	1.450 (3)
C23A—H23A	0.9600	C23B—H23D	0.9600
C23A—H23B	0.9600	C23B—H23E	0.9600
C23A—H23C	0.9600	C23B—H23F	0.9600
C24A—O2A	1.435 (2)	C24B—O2B	1.439 (3)
C24A—C25A	1.490 (3)	C24B—C25B	1.479 (4)
C24A—H24A	0.9700	C24B—H24C	0.9700
C24A—H24B	0.9700	C24B—H24D	0.9700
C25A—H25A	0.9600	C25B—H25D	0.9600
C25A—H25B	0.9600	C25B—H25E	0.9600
C25A—H25C	0.9600	C25B—H25F	0.9600
N2A—H1N	0.84 (2)	N2B—H2N	0.86 (2)
N2A—C1A—C2A	113.27 (16)	N2B—C1B—C2B	113.69 (17)
N2A—C1A—C8A	112.80 (16)	N2B—C1B—C8B	113.14 (17)
C2A—C1A—C8A	101.69 (16)	C2B—C1B—C8B	101.84 (16)
N2A—C1A—C9A	110.65 (15)	N2B—C1B—C9B	108.97 (16)
C2A—C1A—C9A	110.55 (16)	C2B—C1B—C9B	110.80 (16)
C8A—C1A—C9A	107.44 (15)	C8B—C1B—C9B	108.15 (16)
C3A—C2A—C7A	120.3 (2)	C3B—C2B—C7B	120.1 (2)
C3A—C2A—C1A	130.78 (19)	C3B—C2B—C1B	131.3 (2)
C7A—C2A—C1A	108.87 (18)	C7B—C2B—C1B	108.56 (18)
C2A—C3A—C4A	118.8 (2)	C2B—C3B—C4B	119.3 (2)
C2A—C3A—H3A	120.6	C2B—C3B—H3B	120.3
C4A—C3A—H3A	120.6	C4B—C3B—H3B	120.3
C5A—C4A—C3A	120.0 (2)	C5B—C4B—C3B	119.9 (2)
C5A—C4A—H4A	120.0	C5B—C4B—H4B	120.0
C3A—C4A—H4A	120.0	C3B—C4B—H4B	120.0
C4A—C5A—C6A	121.6 (2)	C4B—C5B—C6B	121.9 (2)
C4A—C5A—H5A	119.2	C4B—C5B—H5B	119.1
C6A—C5A—H5A	119.2	C6B—C5B—H5B	119.1
C7A—C6A—C5A	117.9 (2)	C7B—C6B—C5B	117.2 (2)
C7A—C6A—H6A	121.1	C7B—C6B—H6B	121.4
C5A—C6A—H6A	121.1	C5B—C6B—H6B	121.4
C6A—C7A—C2A	121.3 (2)	C6B—C7B—C2B	121.6 (2)
C6A—C7A—N1A	128.8 (2)	C6B—C7B—N1B	128.3 (2)
C2A—C7A—N1A	109.91 (18)	C2B—C7B—N1B	110.04 (18)
O1A—C8A—N1A	126.0 (2)	O1B—C8B—N1B	125.9 (2)
O1A—C8A—C1A	126.0 (2)	O1B—C8B—C1B	126.2 (2)
N1A—C8A—C1A	107.86 (18)	N1B—C8B—C1B	107.87 (17)
O2A—C9A—C10A	111.64 (16)	O2B—C9B—C10B	111.27 (16)
O2A—C9A—C21A	109.21 (16)	O2B—C9B—C21B	109.05 (17)
C10A—C9A—C21A	111.47 (16)	C10B—C9B—C21B	110.80 (17)
O2A—C9A—C1A	103.06 (14)	O2B—C9B—C1B	102.96 (15)
C10A—C9A—C1A	109.23 (15)	C10B—C9B—C1B	109.91 (16)
C21A—C9A—C1A	111.96 (16)	C21B—C9B—C1B	112.62 (16)
C15A—C10A—C11A	118.1 (2)	C11B—C10B—C15B	118.4 (2)
C15A—C10A—C9A	122.57 (19)	C11B—C10B—C9B	118.9 (2)
C11A—C10A—C9A	119.12 (19)	C15B—C10B—C9B	122.5 (2)
C12A—C11A—C10A	120.8 (2)	C10B—C11B—C12B	121.0 (2)
C12A—C11A—H11A	119.6	C10B—C11B—H11B	119.5
C10A—C11A—H11A	119.6	C12B—C11B—H11B	119.5
C13A—C12A—C11A	120.0 (2)	C13B—C12B—C11B	119.5 (3)
C13A—C12A—H12A	120.0	C13B—C12B—H12B	120.2
C11A—C12A—H12A	120.0	C11B—C12B—H12B	120.2
C14A—C13A—C12A	120.2 (2)	C14B—C13B—C12B	120.2 (2)
C14A—C13A—H13A	119.9	C14B—C13B—H13B	119.9
C12A—C13A—H13A	119.9	C12B—C13B—H13B	119.9
C13A—C14A—C15A	120.0 (2)	C13B—C14B—C15B	120.5 (3)
C13A—C14A—H14A	120.0	C13B—C14B—H14B	119.7
C15A—C14A—H14A	120.0	C15B—C14B—H14B	119.7
C10A—C15A—C14A	120.9 (2)	C14B—C15B—C10B	120.3 (2)
C10A—C15A—H15A	119.6	C14B—C15B—H15B	119.9
C14A—C15A—H15A	119.6	C10B—C15B—H15B	119.9
O5A—C16A—O6A	125.26 (19)	O5B—C16B—O6B	125.9 (2)
O5A—C16A—N2A	124.36 (19)	O5B—C16B—N2B	123.5 (2)
O6A—C16A—N2A	110.37 (17)	O6B—C16B—N2B	110.62 (19)
O6A—C17A—C19A	110.3 (2)	O6B—C17B—C19B	110.2 (2)
O6A—C17A—C20A	102.10 (19)	O6B—C17B—C18B	109.4 (2)
C19A—C17A—C20A	110.8 (2)	C19B—C17B—C18B	112.5 (3)
O6A—C17A—C18A	109.5 (2)	O6B—C17B—C20B	102.1 (2)
C19A—C17A—C18A	111.8 (2)	C19B—C17B—C20B	111.1 (3)
C20A—C17A—C18A	111.9 (3)	C18B—C17B—C20B	111.0 (3)
C17A—C18A—H18A	109.5	C17B—C18B—H18D	109.5
C17A—C18A—H18B	109.5	C17B—C18B—H18E	109.5
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
C17A—C18A—H18C	109.5	C17B—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5
C17A—C19A—H19A	109.5	C17B—C19B—H19D	109.5
C17A—C19A—H19B	109.5	C17B—C19B—H19E	109.5
H19A—C19A—H19B	109.5	H19D—C19B—H19E	109.5
C17A—C19A—H19C	109.5	C17B—C19B—H19F	109.5
H19A—C19A—H19C	109.5	H19D—C19B—H19F	109.5
H19B—C19A—H19C	109.5	H19E—C19B—H19F	109.5
C17A—C20A—H20A	109.5	C17B—C20B—H20D	109.5
C17A—C20A—H20B	109.5	C17B—C20B—H20E	109.5
H20A—C20A—H20B	109.5	H20D—C20B—H20E	109.5
C17A—C20A—H20C	109.5	C17B—C20B—H20F	109.5
H20A—C20A—H20C	109.5	H20D—C20B—H20F	109.5
H20B—C20A—H20C	109.5	H20E—C20B—H20F	109.5
O3A—C21A—O4A	123.6 (2)	O3B—C21B—O4B	122.7 (2)
O3A—C21A—C9A	124.9 (2)	O3B—C21B—C9B	125.6 (2)
O4A—C21A—C9A	111.33 (17)	O4B—C21B—C9B	111.4 (2)
O4A—C22A—H22A	109.5	O4B—C22B—H22D	109.5
O4A—C22A—H22B	109.5	O4B—C22B—H22E	109.5
H22A—C22A—H22B	109.5	H22D—C22B—H22E	109.5
O4A—C22A—H22C	109.5	O4B—C22B—H22F	109.5
H22A—C22A—H22C	109.5	H22D—C22B—H22F	109.5
H22B—C22A—H22C	109.5	H22E—C22B—H22F	109.5
N1A—C23A—H23A	109.5	N1B—C23B—H23D	109.5
N1A—C23A—H23B	109.5	N1B—C23B—H23E	109.5
H23A—C23A—H23B	109.5	H23D—C23B—H23E	109.5
N1A—C23A—H23C	109.5	N1B—C23B—H23F	109.5
H23A—C23A—H23C	109.5	H23D—C23B—H23F	109.5
H23B—C23A—H23C	109.5	H23E—C23B—H23F	109.5
O2A—C24A—C25A	108.25 (18)	O2B—C24B—C25B	107.6 (2)
O2A—C24A—H24A	110.0	O2B—C24B—H24C	110.2
C25A—C24A—H24A	110.0	C25B—C24B—H24C	110.2
O2A—C24A—H24B	110.0	O2B—C24B—H24D	110.2
C25A—C24A—H24B	110.0	C25B—C24B—H24D	110.2
H24A—C24A—H24B	108.4	H24C—C24B—H24D	108.5
C24A—C25A—H25A	109.5	C24B—C25B—H25D	109.5
C24A—C25A—H25B	109.5	C24B—C25B—H25E	109.5
H25A—C25A—H25B	109.5	H25D—C25B—H25E	109.5
C24A—C25A—H25C	109.5	C24B—C25B—H25F	109.5
H25A—C25A—H25C	109.5	H25D—C25B—H25F	109.5
H25B—C25A—H25C	109.5	H25E—C25B—H25F	109.5
C8A—N1A—C7A	111.31 (17)	C8B—N1B—C7B	111.07 (17)
C8A—N1A—C23A	122.5 (2)	C8B—N1B—C23B	123.69 (19)
C7A—N1A—C23A	126.2 (2)	C7B—N1B—C23B	125.17 (19)
C16A—N2A—C1A	124.62 (17)	C16B—N2B—C1B	124.48 (18)
C16A—N2A—H1N	116.2 (15)	C16B—N2B—H2N	116.9 (15)
C1A—N2A—H1N	118.8 (15)	C1B—N2B—H2N	118.1 (16)
C9A—O2A—C24A	116.60 (15)	C9B—O2B—C24B	117.05 (16)
C21A—O4A—C22A	117.06 (18)	C21B—O4B—C22B	117.2 (2)
C16A—O6A—C17A	121.78 (16)	C16B—O6B—C17B	123.14 (17)
N2A—C1A—C2A—C3A	53.6 (3)	N2B—C1B—C2B—C3B	50.6 (3)
C8A—C1A—C2A—C3A	174.9 (2)	C8B—C1B—C2B—C3B	172.6 (2)
C9A—C1A—C2A—C3A	−71.2 (3)	C9B—C1B—C2B—C3B	−72.5 (3)
N2A—C1A—C2A—C7A	−125.17 (19)	N2B—C1B—C2B—C7B	−127.66 (19)
C8A—C1A—C2A—C7A	−3.9 (2)	C8B—C1B—C2B—C7B	−5.6 (2)
C9A—C1A—C2A—C7A	110.00 (18)	C9B—C1B—C2B—C7B	109.22 (19)
C7A—C2A—C3A—C4A	−1.5 (3)	C7B—C2B—C3B—C4B	−1.2 (3)
C1A—C2A—C3A—C4A	179.8 (2)	C1B—C2B—C3B—C4B	−179.3 (2)
C2A—C3A—C4A—C5A	1.5 (4)	C2B—C3B—C4B—C5B	0.8 (4)
C3A—C4A—C5A—C6A	−0.6 (4)	C3B—C4B—C5B—C6B	−0.1 (4)
C4A—C5A—C6A—C7A	−0.3 (4)	C4B—C5B—C6B—C7B	−0.2 (4)
C5A—C6A—C7A—C2A	0.4 (3)	C5B—C6B—C7B—C2B	−0.2 (3)
C5A—C6A—C7A—N1A	178.9 (2)	C5B—C6B—C7B—N1B	177.1 (2)
C3A—C2A—C7A—C6A	0.5 (3)	C3B—C2B—C7B—C6B	0.9 (3)
C1A—C2A—C7A—C6A	179.5 (2)	C1B—C2B—C7B—C6B	179.4 (2)
C3A—C2A—C7A—N1A	−178.20 (18)	C3B—C2B—C7B—N1B	−176.84 (19)
C1A—C2A—C7A—N1A	0.7 (2)	C1B—C2B—C7B—N1B	1.6 (2)
N2A—C1A—C8A—O1A	−55.9 (3)	N2B—C1B—C8B—O1B	−52.8 (3)
C2A—C1A—C8A—O1A	−177.6 (2)	C2B—C1B—C8B—O1B	−175.3 (2)
C9A—C1A—C8A—O1A	66.3 (2)	C9B—C1B—C8B—O1B	68.0 (3)
N2A—C1A—C8A—N1A	127.41 (18)	N2B—C1B—C8B—N1B	130.25 (18)
C2A—C1A—C8A—N1A	5.8 (2)	C2B—C1B—C8B—N1B	7.8 (2)
C9A—C1A—C8A—N1A	−110.38 (18)	C9B—C1B—C8B—N1B	−108.94 (18)
N2A—C1A—C9A—O2A	−52.93 (19)	N2B—C1B—C9B—O2B	−56.7 (2)
C2A—C1A—C9A—O2A	73.38 (19)	C2B—C1B—C9B—O2B	69.08 (19)
C8A—C1A—C9A—O2A	−176.46 (15)	C8B—C1B—C9B—O2B	179.91 (15)
N2A—C1A—C9A—C10A	−171.73 (16)	N2B—C1B—C9B—C10B	−175.36 (17)
C2A—C1A—C9A—C10A	−45.4 (2)	C2B—C1B—C9B—C10B	−49.6 (2)
C8A—C1A—C9A—C10A	64.7 (2)	C8B—C1B—C9B—C10B	61.3 (2)
N2A—C1A—C9A—C21A	64.3 (2)	N2B—C1B—C9B—C21B	60.6 (2)
C2A—C1A—C9A—C21A	−169.39 (16)	C2B—C1B—C9B—C21B	−173.61 (18)
C8A—C1A—C9A—C21A	−59.2 (2)	C8B—C1B—C9B—C21B	−62.8 (2)
O2A—C9A—C10A—C15A	165.85 (18)	O2B—C9B—C10B—C11B	−20.5 (3)
C21A—C9A—C10A—C15A	43.4 (3)	C21B—C9B—C10B—C11B	−142.1 (2)
C1A—C9A—C10A—C15A	−80.8 (2)	C1B—C9B—C10B—C11B	92.8 (2)
O2A—C9A—C10A—C11A	−19.2 (3)	O2B—C9B—C10B—C15B	162.66 (19)
C21A—C9A—C10A—C11A	−141.6 (2)	C21B—C9B—C10B—C15B	41.2 (3)
C1A—C9A—C10A—C11A	94.1 (2)	C1B—C9B—C10B—C15B	−83.9 (2)
C15A—C10A—C11A—C12A	0.8 (3)	C15B—C10B—C11B—C12B	−1.1 (3)
C9A—C10A—C11A—C12A	−174.4 (2)	C9B—C10B—C11B—C12B	−178.0 (2)
C10A—C11A—C12A—C13A	0.1 (4)	C10B—C11B—C12B—C13B	−0.7 (4)
C11A—C12A—C13A—C14A	−0.9 (4)	C11B—C12B—C13B—C14B	1.6 (4)
C12A—C13A—C14A—C15A	0.8 (4)	C12B—C13B—C14B—C15B	−0.7 (4)
C11A—C10A—C15A—C14A	−0.9 (3)	C13B—C14B—C15B—C10B	−1.2 (4)
C9A—C10A—C15A—C14A	174.1 (2)	C11B—C10B—C15B—C14B	2.1 (3)
C13A—C14A—C15A—C10A	0.2 (4)	C9B—C10B—C15B—C14B	178.9 (2)
O2A—C9A—C21A—O3A	−117.2 (2)	O2B—C9B—C21B—O3B	−121.5 (3)
C10A—C9A—C21A—O3A	6.6 (3)	C10B—C9B—C21B—O3B	1.3 (3)
C1A—C9A—C21A—O3A	129.3 (2)	C1B—C9B—C21B—O3B	124.9 (3)
O2A—C9A—C21A—O4A	58.6 (2)	O2B—C9B—C21B—O4B	52.9 (2)
C10A—C9A—C21A—O4A	−177.58 (17)	C10B—C9B—C21B—O4B	175.66 (18)
C1A—C9A—C21A—O4A	−54.9 (2)	C1B—C9B—C21B—O4B	−60.8 (2)
O1A—C8A—N1A—C7A	177.6 (2)	O1B—C8B—N1B—C7B	175.6 (2)
C1A—C8A—N1A—C7A	−5.8 (2)	C1B—C8B—N1B—C7B	−7.4 (2)
O1A—C8A—N1A—C23A	−1.0 (3)	O1B—C8B—N1B—C23B	−1.5 (3)
C1A—C8A—N1A—C23A	175.7 (2)	C1B—C8B—N1B—C23B	175.44 (19)
C6A—C7A—N1A—C8A	−175.3 (2)	C6B—C7B—N1B—C8B	−173.8 (2)
C2A—C7A—N1A—C8A	3.3 (2)	C2B—C7B—N1B—C8B	3.8 (2)
C6A—C7A—N1A—C23A	3.2 (4)	C6B—C7B—N1B—C23B	3.3 (4)
C2A—C7A—N1A—C23A	−178.2 (2)	C2B—C7B—N1B—C23B	−179.1 (2)
O5A—C16A—N2A—C1A	−173.4 (2)	O5B—C16B—N2B—C1B	−176.9 (2)
O6A—C16A—N2A—C1A	7.5 (3)	O6B—C16B—N2B—C1B	3.6 (3)
C2A—C1A—N2A—C16A	59.3 (3)	C2B—C1B—N2B—C16B	65.8 (3)
C8A—C1A—N2A—C16A	−55.5 (3)	C8B—C1B—N2B—C16B	−49.8 (3)
C9A—C1A—N2A—C16A	−175.91 (18)	C9B—C1B—N2B—C16B	−170.1 (2)
C10A—C9A—O2A—C24A	−76.2 (2)	C10B—C9B—O2B—C24B	−74.8 (2)
C21A—C9A—O2A—C24A	47.6 (2)	C21B—C9B—O2B—C24B	47.7 (2)
C1A—C9A—O2A—C24A	166.73 (16)	C1B—C9B—O2B—C24B	167.47 (17)
C25A—C24A—O2A—C9A	154.35 (18)	C25B—C24B—O2B—C9B	160.2 (2)
O3A—C21A—O4A—C22A	−7.3 (3)	O3B—C21B—O4B—C22B	−2.7 (4)
C9A—C21A—O4A—C22A	176.8 (2)	C9B—C21B—O4B—C22B	−177.3 (2)
O5A—C16A—O6A—C17A	8.0 (3)	O5B—C16B—O6B—C17B	−1.6 (4)
N2A—C16A—O6A—C17A	−172.83 (19)	N2B—C16B—O6B—C17B	177.8 (2)
C19A—C17A—O6A—C16A	−65.8 (3)	C19B—C17B—O6B—C16B	60.3 (3)
C20A—C17A—O6A—C16A	176.4 (2)	C18B—C17B—O6B—C16B	−63.9 (3)
C18A—C17A—O6A—C16A	57.7 (3)	C20B—C17B—O6B—C16B	178.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H1N···O2A	0.84 (2)	2.40 (2)	2.702 (2)	102 (2)
N2A—H1N···O4A	0.84 (2)	2.35 (2)	2.709 (2)	106 (2)
N2A—H1N···O5A^i	0.84 (2)	2.22 (2)	3.040 (2)	165 (2)
N2B—H2N···O2B	0.86 (2)	2.38 (2)	2.706 (2)	103 (2)
N2B—H2N···O4B	0.86 (2)	2.33 (2)	2.699 (2)	106 (2)
N2B—H2N···O5B^ii	0.86 (2)	2.35 (2)	3.190 (3)	166 (2)
C5A—H5A···O1B^ii	0.93	2.54	3.453 (3)	167
C5B—H5B···O1A^i	0.93	2.57	3.377 (3)	146
C11A—H11A···O2A	0.93	2.41	2.767 (3)	103
C11B—H11B···O2B	0.93	2.40	2.756 (3)	103
C15A—H15A···O3A	0.93	2.45	2.866 (3)	107
C15B—H15B···O3B	0.93	2.38	2.793 (3)	107
C23B—H23E···O1B^iii	0.96	2.45	3.247 (3)	140

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

(III) Methyl 2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-[(4-methoxybenzyl)oxy]-2-phenylacetate

Crystal data

C31H34N2O7	F(000) = 1160
Mr = 546.60	Dx = 1.223 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.9402 (12) Å	Cell parameters from 7058 reflections
b = 16.5380 (15) Å	θ = 2.7–28.0°
c = 14.3279 (13) Å	µ = 0.09 mm^−1
β = 116.042 (1)°	T = 294 K
V = 2967.8 (5) Å^3	Needle, colourless
Z = 4	0.18 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5669 reflections with I > 2σ(I)
ω scans	Rint = 0.021
Absorption correction: multi-scan (SADABS; Bruker, 2001)	θmax = 28.4°, θmin = 2.0°
Tmin = 0.89, Tmax = 0.95	h = −18→18
34269 measured reflections	k = −21→21
7183 independent reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.133	w = 1/[σ^2(Fo^2) + (0.0623P)^2 + 0.601P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
7183 reflections	Δρmax = 0.26 e Å^−3
371 parameters	Δρmin = −0.17 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
C1	0.82534 (9)	−0.00324 (7)	0.13654 (9)	0.0406 (2)
C2	0.83083 (11)	−0.06507 (8)	0.06144 (9)	0.0481 (3)
C3	0.91073 (14)	−0.08249 (10)	0.03255 (11)	0.0648 (4)
H3	0.9727	−0.0516	0.0568	0.078*
C4	0.8962 (2)	−0.14762 (14)	−0.03394 (14)	0.0889 (6)
H4	0.9489	−0.1603	−0.0548	0.107*
C5	0.8049 (2)	−0.19308 (13)	−0.06885 (15)	0.0978 (7)
H5	0.7976	−0.2371	−0.1118	0.117*
C6	0.72295 (17)	−0.17534 (10)	−0.04211 (13)	0.0806 (5)
H6	0.6609	−0.2062	−0.0667	0.097*
C7	0.73723 (12)	−0.10978 (8)	0.02271 (10)	0.0543 (3)
C8	0.70961 (10)	−0.01403 (7)	0.12259 (10)	0.0450 (3)
C9	0.90422 (9)	−0.02661 (7)	0.25239 (9)	0.0416 (3)
C10	0.89224 (11)	−0.11697 (8)	0.26912 (9)	0.0512 (3)
C11	0.96059 (13)	−0.17123 (9)	0.25477 (12)	0.0673 (4)
H11	1.0158	−0.1522	0.2409	0.081*
C12	0.9469 (2)	−0.25362 (11)	0.26102 (18)	0.0986 (7)
H12	0.9929	−0.2895	0.2511	0.118*
C13	0.8663 (2)	−0.28278 (13)	0.28173 (19)	0.1129 (9)
H13	0.8575	−0.3382	0.2858	0.135*
C14	0.79884 (19)	−0.22973 (13)	0.29635 (16)	0.0950 (7)
H14	0.7443	−0.2495	0.3107	0.114*
C15	0.81045 (13)	−0.14654 (10)	0.29010 (12)	0.0676 (4)
H15	0.7639	−0.1111	0.2999	0.081*
C16	0.78225 (10)	0.11717 (8)	0.02821 (10)	0.0475 (3)
C17	0.77520 (14)	0.24504 (10)	−0.06193 (13)	0.0704 (4)
C18	0.8440 (2)	0.31997 (14)	−0.0216 (2)	0.1356 (11)
H18A	0.9176	0.3059	0.0011	0.203*
H18B	0.8343	0.3420	0.0357	0.203*
H18C	0.8235	0.3595	−0.0761	0.203*
C19	0.6611 (2)	0.26376 (16)	−0.0879 (2)	0.1202 (9)
H19A	0.6561	0.2822	−0.0266	0.180*
H19B	0.6186	0.2159	−0.1136	0.180*
H19C	0.6353	0.3052	−0.1400	0.180*
C20	0.7903 (3)	0.20732 (16)	−0.14872 (18)	0.1221 (9)
H20A	0.7449	0.1608	−0.1735	0.183*
H20B	0.8634	0.1912	−0.1246	0.183*
H20C	0.7722	0.2457	−0.2042	0.183*
C21	0.88721 (10)	0.02642 (8)	0.33369 (10)	0.0493 (3)
C22	0.91029 (17)	0.15583 (11)	0.40727 (14)	0.0803 (5)
H22A	0.9650	0.1399	0.4738	0.120*
H22B	0.8418	0.1521	0.4079	0.120*
H22C	0.9225	0.2105	0.3929	0.120*
C23	0.55985 (13)	−0.10833 (11)	0.03195 (17)	0.0804 (5)
H23A	0.5306	−0.0809	0.0727	0.121*
H23B	0.5624	−0.1654	0.0452	0.121*
H23C	0.5157	−0.0983	−0.0404	0.121*
C24	1.09378 (10)	−0.01437 (10)	0.36065 (10)	0.0550 (3)
H24A	1.0846	−0.0611	0.3968	0.066*
H24B	1.0957	0.0336	0.4004	0.066*
C25	1.19566 (10)	−0.02168 (8)	0.35076 (10)	0.0486 (3)
C26	1.20909 (12)	0.01102 (10)	0.26933 (11)	0.0609 (4)
H26	1.1521	0.0375	0.2167	0.073*
C27	1.30541 (14)	0.00562 (11)	0.26357 (13)	0.0684 (4)
H27	1.3128	0.0276	0.2073	0.082*
C28	1.38968 (13)	−0.03243 (12)	0.34163 (15)	0.0754 (5)
C29	1.37769 (15)	−0.06442 (16)	0.42428 (17)	0.0989 (7)
H29	1.4352	−0.0896	0.4777	0.119*
C30	1.28185 (13)	−0.05951 (13)	0.42866 (14)	0.0786 (5)
H30	1.2747	−0.0819	0.4848	0.094*
C31	1.5083 (2)	−0.0052 (2)	0.2669 (2)	0.1266 (10)
H31A	1.4937	0.0517	0.2650	0.190*
H31B	1.4632	−0.0288	0.2008	0.190*
H31C	1.5818	−0.0132	0.2815	0.190*
N1	0.66679 (9)	−0.07877 (7)	0.05974 (9)	0.0529 (3)
N2	0.84687 (9)	0.07870 (6)	0.11669 (9)	0.0485 (3)
H1N	0.9002 (13)	0.1033 (10)	0.1614 (13)	0.063 (5)*
O1	0.66731 (8)	0.02638 (6)	0.16426 (8)	0.0599 (3)
O2	1.00623 (7)	−0.00904 (5)	0.25817 (6)	0.0466 (2)
O3	0.86239 (12)	0.00161 (8)	0.39768 (9)	0.0813 (4)
O4	0.91250 (9)	0.10310 (6)	0.32800 (8)	0.0608 (3)
O5	0.70289 (9)	0.08816 (6)	−0.03873 (8)	0.0678 (3)
O6	0.82138 (8)	0.19135 (6)	0.02922 (8)	0.0622 (3)
O7	1.48819 (11)	−0.04174 (13)	0.34421 (14)	0.1203 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0432 (6)	0.0395 (6)	0.0361 (5)	−0.0002 (4)	0.0148 (5)	0.0048 (4)
C2	0.0568 (7)	0.0479 (7)	0.0348 (6)	0.0085 (5)	0.0157 (5)	0.0058 (5)
C3	0.0749 (10)	0.0765 (10)	0.0468 (7)	0.0199 (8)	0.0302 (7)	0.0102 (7)
C4	0.1176 (16)	0.0980 (14)	0.0561 (9)	0.0409 (13)	0.0426 (11)	0.0032 (9)
C5	0.142 (2)	0.0807 (13)	0.0547 (10)	0.0318 (13)	0.0279 (12)	−0.0160 (9)
C6	0.0999 (13)	0.0578 (9)	0.0559 (9)	0.0025 (9)	0.0082 (9)	−0.0114 (7)
C7	0.0641 (8)	0.0447 (7)	0.0392 (6)	0.0049 (6)	0.0090 (6)	0.0019 (5)
C8	0.0436 (6)	0.0416 (6)	0.0448 (6)	0.0002 (5)	0.0149 (5)	0.0071 (5)
C9	0.0418 (6)	0.0456 (6)	0.0354 (5)	−0.0031 (5)	0.0152 (5)	0.0042 (4)
C10	0.0563 (7)	0.0473 (7)	0.0378 (6)	−0.0030 (5)	0.0094 (5)	0.0096 (5)
C11	0.0709 (9)	0.0525 (8)	0.0585 (8)	0.0100 (7)	0.0099 (7)	0.0110 (7)
C12	0.1081 (16)	0.0518 (9)	0.0919 (14)	0.0154 (10)	0.0033 (12)	0.0125 (9)
C13	0.130 (2)	0.0518 (10)	0.1004 (16)	−0.0149 (12)	−0.0011 (14)	0.0284 (10)
C14	0.1024 (15)	0.0798 (13)	0.0769 (12)	−0.0358 (12)	0.0155 (11)	0.0257 (10)
C15	0.0720 (9)	0.0676 (9)	0.0537 (8)	−0.0192 (7)	0.0188 (7)	0.0134 (7)
C16	0.0530 (7)	0.0440 (6)	0.0449 (6)	0.0017 (5)	0.0210 (6)	0.0060 (5)
C17	0.0808 (11)	0.0545 (8)	0.0688 (10)	0.0075 (7)	0.0263 (8)	0.0272 (7)
C18	0.155 (2)	0.0686 (13)	0.140 (2)	−0.0254 (14)	0.0252 (18)	0.0473 (14)
C19	0.0989 (16)	0.1063 (17)	0.145 (2)	0.0431 (14)	0.0445 (16)	0.0588 (17)
C20	0.180 (3)	0.121 (2)	0.0800 (14)	0.0206 (18)	0.0705 (17)	0.0366 (14)
C21	0.0485 (7)	0.0590 (8)	0.0394 (6)	−0.0056 (6)	0.0183 (5)	−0.0016 (5)
C22	0.1025 (13)	0.0700 (10)	0.0695 (10)	−0.0016 (9)	0.0388 (10)	−0.0209 (8)
C23	0.0534 (9)	0.0636 (10)	0.1004 (13)	−0.0154 (7)	0.0118 (8)	0.0030 (9)
C24	0.0457 (7)	0.0748 (9)	0.0374 (6)	−0.0034 (6)	0.0119 (5)	0.0035 (6)
C25	0.0460 (6)	0.0518 (7)	0.0436 (6)	−0.0039 (5)	0.0155 (5)	−0.0011 (5)
C26	0.0549 (8)	0.0767 (10)	0.0493 (7)	0.0018 (7)	0.0214 (6)	0.0073 (7)
C27	0.0689 (9)	0.0864 (11)	0.0589 (9)	−0.0084 (8)	0.0362 (8)	−0.0006 (8)
C28	0.0532 (8)	0.0977 (13)	0.0812 (11)	0.0031 (8)	0.0349 (8)	−0.0014 (10)
C29	0.0606 (10)	0.143 (2)	0.0907 (14)	0.0324 (11)	0.0312 (10)	0.0464 (14)
C30	0.0576 (9)	0.1074 (14)	0.0699 (10)	0.0159 (9)	0.0274 (8)	0.0347 (10)
C31	0.0940 (16)	0.189 (3)	0.129 (2)	−0.0221 (17)	0.0795 (17)	−0.007 (2)
N1	0.0475 (6)	0.0455 (6)	0.0523 (6)	−0.0062 (4)	0.0097 (5)	0.0020 (5)
N2	0.0515 (6)	0.0427 (5)	0.0434 (5)	−0.0070 (5)	0.0135 (5)	0.0070 (4)
O1	0.0554 (5)	0.0580 (6)	0.0722 (6)	0.0039 (4)	0.0334 (5)	−0.0009 (5)
O2	0.0406 (4)	0.0601 (5)	0.0360 (4)	−0.0030 (4)	0.0140 (3)	0.0047 (4)
O3	0.1143 (10)	0.0899 (8)	0.0602 (7)	−0.0290 (7)	0.0572 (7)	−0.0133 (6)
O4	0.0792 (7)	0.0521 (5)	0.0561 (6)	−0.0047 (5)	0.0343 (5)	−0.0071 (4)
O5	0.0664 (6)	0.0605 (6)	0.0532 (6)	−0.0071 (5)	0.0048 (5)	0.0117 (5)
O6	0.0726 (6)	0.0456 (5)	0.0572 (6)	−0.0043 (4)	0.0183 (5)	0.0144 (4)
O7	0.0698 (9)	0.1857 (18)	0.1236 (13)	0.0209 (10)	0.0592 (9)	0.0232 (12)

Geometric parameters (Å, º)

C1—N2	1.4429 (15)	C18—H18B	0.9600
C1—C2	1.5105 (17)	C18—H18C	0.9600
C1—C8	1.5463 (17)	C19—H19A	0.9600
C1—C9	1.5847 (15)	C19—H19B	0.9600
C2—C3	1.378 (2)	C19—H19C	0.9600
C2—C7	1.386 (2)	C20—H20A	0.9600
C3—C4	1.393 (3)	C20—H20B	0.9600
C3—H3	0.9300	C20—H20C	0.9600
C4—C5	1.371 (3)	C21—O3	1.1864 (16)
C4—H4	0.9300	C21—O4	1.3282 (17)
C5—C6	1.386 (3)	C22—O4	1.4429 (18)
C5—H5	0.9300	C22—H22A	0.9600
C6—C7	1.384 (2)	C22—H22B	0.9600
C6—H6	0.9300	C22—H22C	0.9600
C7—N1	1.4023 (19)	C23—N1	1.4487 (19)
C8—O1	1.2083 (16)	C23—H23A	0.9600
C8—N1	1.3570 (17)	C23—H23B	0.9600
C9—O2	1.4177 (14)	C23—H23C	0.9600
C9—C10	1.5343 (17)	C24—O2	1.4422 (14)
C9—C21	1.5571 (17)	C24—C25	1.4927 (19)
C10—C11	1.388 (2)	C24—H24A	0.9700
C10—C15	1.389 (2)	C24—H24B	0.9700
C11—C12	1.384 (2)	C25—C26	1.3713 (19)
C11—H11	0.9300	C25—C30	1.380 (2)
C12—C13	1.369 (4)	C26—C27	1.384 (2)
C12—H12	0.9300	C26—H26	0.9300
C13—C14	1.368 (4)	C27—C28	1.369 (2)
C13—H13	0.9300	C27—H27	0.9300
C14—C15	1.393 (3)	C28—O7	1.366 (2)
C14—H14	0.9300	C28—C29	1.373 (3)
C15—H15	0.9300	C29—C30	1.367 (2)
C16—O5	1.2010 (16)	C29—H29	0.9300
C16—O6	1.3401 (15)	C30—H30	0.9300
C16—N2	1.3493 (16)	C31—O7	1.395 (3)
C17—O6	1.4731 (17)	C31—H31A	0.9600
C17—C20	1.486 (3)	C31—H31B	0.9600
C17—C19	1.499 (3)	C31—H31C	0.9600
C17—C18	1.517 (3)	N2—H1N	0.843 (17)
C18—H18A	0.9600
N2—C1—C2	114.54 (10)	C17—C19—H19B	109.5
N2—C1—C8	112.23 (10)	H19A—C19—H19B	109.5
C2—C1—C8	101.89 (10)	C17—C19—H19C	109.5
N2—C1—C9	109.07 (9)	H19A—C19—H19C	109.5
C2—C1—C9	110.62 (9)	H19B—C19—H19C	109.5
C8—C1—C9	108.18 (9)	C17—C20—H20A	109.5
C3—C2—C7	120.73 (13)	C17—C20—H20B	109.5
C3—C2—C1	130.98 (13)	H20A—C20—H20B	109.5
C7—C2—C1	108.25 (11)	C17—C20—H20C	109.5
C2—C3—C4	118.26 (18)	H20A—C20—H20C	109.5
C2—C3—H3	120.9	H20B—C20—H20C	109.5
C4—C3—H3	120.9	O3—C21—O4	123.57 (13)
C5—C4—C3	120.41 (18)	O3—C21—C9	125.11 (13)
C5—C4—H4	119.8	O4—C21—C9	111.11 (10)
C3—C4—H4	119.8	O4—C22—H22A	109.5
C4—C5—C6	121.98 (17)	O4—C22—H22B	109.5
C4—C5—H5	119.0	H22A—C22—H22B	109.5
C6—C5—H5	119.0	O4—C22—H22C	109.5
C7—C6—C5	117.26 (19)	H22A—C22—H22C	109.5
C7—C6—H6	121.4	H22B—C22—H22C	109.5
C5—C6—H6	121.4	N1—C23—H23A	109.5
C6—C7—C2	121.29 (16)	N1—C23—H23B	109.5
C6—C7—N1	128.47 (15)	H23A—C23—H23B	109.5
C2—C7—N1	110.23 (11)	N1—C23—H23C	109.5
O1—C8—N1	126.60 (12)	H23A—C23—H23C	109.5
O1—C8—C1	125.45 (11)	H23B—C23—H23C	109.5
N1—C8—C1	107.88 (11)	O2—C24—C25	108.87 (10)
O2—C9—C10	111.45 (10)	O2—C24—H24A	109.9
O2—C9—C21	108.61 (9)	C25—C24—H24A	109.9
C10—C9—C21	111.65 (10)	O2—C24—H24B	109.9
O2—C9—C1	103.19 (8)	C25—C24—H24B	109.9
C10—C9—C1	109.15 (9)	H24A—C24—H24B	108.3
C21—C9—C1	112.50 (10)	C26—C25—C30	118.12 (13)
C11—C10—C15	119.10 (14)	C26—C25—C24	122.67 (12)
C11—C10—C9	118.53 (13)	C30—C25—C24	119.14 (13)
C15—C10—C9	122.18 (13)	C25—C26—C27	121.59 (14)
C12—C11—C10	120.22 (19)	C25—C26—H26	119.2
C12—C11—H11	119.9	C27—C26—H26	119.2
C10—C11—H11	119.9	C28—C27—C26	119.21 (15)
C13—C12—C11	120.7 (2)	C28—C27—H27	120.4
C13—C12—H12	119.7	C26—C27—H27	120.4
C11—C12—H12	119.7	O7—C28—C27	124.46 (17)
C14—C13—C12	119.46 (18)	O7—C28—C29	115.78 (17)
C14—C13—H13	120.3	C27—C28—C29	119.76 (15)
C12—C13—H13	120.3	C30—C29—C28	120.55 (17)
C13—C14—C15	121.1 (2)	C30—C29—H29	119.7
C13—C14—H14	119.4	C28—C29—H29	119.7
C15—C14—H14	119.4	C29—C30—C25	120.76 (16)
C10—C15—C14	119.4 (2)	C29—C30—H30	119.6
C10—C15—H15	120.3	C25—C30—H30	119.6
C14—C15—H15	120.3	O7—C31—H31A	109.5
O5—C16—O6	127.03 (12)	O7—C31—H31B	109.5
O5—C16—N2	124.25 (12)	H31A—C31—H31B	109.5
O6—C16—N2	108.72 (11)	O7—C31—H31C	109.5
O6—C17—C20	108.75 (15)	H31A—C31—H31C	109.5
O6—C17—C19	110.33 (15)	H31B—C31—H31C	109.5
C20—C17—C19	113.8 (2)	C8—N1—C7	111.26 (11)
O6—C17—C18	101.39 (15)	C8—N1—C23	123.27 (14)
C20—C17—C18	111.3 (2)	C7—N1—C23	125.42 (13)
C19—C17—C18	110.5 (2)	C16—N2—C1	121.14 (11)
C17—C18—H18A	109.5	C16—N2—H1N	119.3 (11)
C17—C18—H18B	109.5	C1—N2—H1N	119.6 (11)
H18A—C18—H18B	109.5	C9—O2—C24	115.20 (9)
C17—C18—H18C	109.5	C21—O4—C22	115.52 (12)
H18A—C18—H18C	109.5	C16—O6—C17	121.66 (12)
H18B—C18—H18C	109.5	C28—O7—C31	118.68 (19)
C17—C19—H19A	109.5
N2—C1—C2—C3	54.30 (18)	C13—C14—C15—C10	−0.3 (3)
C8—C1—C2—C3	175.72 (13)	O2—C9—C21—O3	−127.09 (15)
C9—C1—C2—C3	−69.45 (16)	C10—C9—C21—O3	−3.80 (19)
N2—C1—C2—C7	−128.07 (11)	C1—C9—C21—O3	119.33 (15)
C8—C1—C2—C7	−6.66 (12)	O2—C9—C21—O4	47.84 (13)
C9—C1—C2—C7	108.18 (11)	C10—C9—C21—O4	171.13 (11)
C7—C2—C3—C4	−1.9 (2)	C1—C9—C21—O4	−65.74 (13)
C1—C2—C3—C4	175.46 (14)	O2—C24—C25—C26	29.36 (19)
C2—C3—C4—C5	−0.3 (3)	O2—C24—C25—C30	−153.72 (15)
C3—C4—C5—C6	1.6 (3)	C30—C25—C26—C27	1.0 (2)
C4—C5—C6—C7	−0.6 (3)	C24—C25—C26—C27	177.93 (15)
C5—C6—C7—C2	−1.7 (2)	C25—C26—C27—C28	−0.8 (3)
C5—C6—C7—N1	179.02 (15)	C26—C27—C28—O7	179.71 (19)
C3—C2—C7—C6	3.0 (2)	C26—C27—C28—C29	−0.1 (3)
C1—C2—C7—C6	−174.93 (13)	O7—C28—C29—C30	−179.0 (2)
C3—C2—C7—N1	−177.59 (12)	C27—C28—C29—C30	0.8 (4)
C1—C2—C7—N1	4.49 (14)	C28—C29—C30—C25	−0.6 (4)
N2—C1—C8—O1	−53.11 (16)	C26—C25—C30—C29	−0.3 (3)
C2—C1—C8—O1	−176.11 (12)	C24—C25—C30—C29	−177.32 (19)
C9—C1—C8—O1	67.28 (15)	O1—C8—N1—C7	178.37 (12)
N2—C1—C8—N1	129.72 (11)	C1—C8—N1—C7	−4.51 (13)
C2—C1—C8—N1	6.72 (12)	O1—C8—N1—C23	1.0 (2)
C9—C1—C8—N1	−109.89 (11)	C1—C8—N1—C23	178.17 (13)
N2—C1—C9—O2	−53.64 (12)	C6—C7—N1—C8	179.46 (14)
C2—C1—C9—O2	73.21 (12)	C2—C7—N1—C8	0.09 (15)
C8—C1—C9—O2	−175.98 (9)	C6—C7—N1—C23	−3.3 (2)
N2—C1—C9—C10	−172.25 (10)	C2—C7—N1—C23	177.34 (13)
C2—C1—C9—C10	−45.41 (13)	O5—C16—N2—C1	1.3 (2)
C8—C1—C9—C10	65.40 (12)	O6—C16—N2—C1	−179.10 (11)
N2—C1—C9—C21	63.23 (12)	C2—C1—N2—C16	63.84 (16)
C2—C1—C9—C21	−169.93 (10)	C8—C1—N2—C16	−51.71 (15)
C8—C1—C9—C21	−59.12 (12)	C9—C1—N2—C16	−171.58 (11)
O2—C9—C10—C11	−19.76 (15)	C10—C9—O2—C24	−71.11 (13)
C21—C9—C10—C11	−141.43 (12)	C21—C9—O2—C24	52.30 (13)
C1—C9—C10—C11	93.56 (13)	C1—C9—O2—C24	171.88 (10)
O2—C9—C10—C15	165.32 (11)	C25—C24—O2—C9	161.47 (11)
C21—C9—C10—C15	43.66 (16)	O3—C21—O4—C22	1.3 (2)
C1—C9—C10—C15	−81.35 (14)	C9—C21—O4—C22	−173.76 (12)
C15—C10—C11—C12	0.2 (2)	O5—C16—O6—C17	−7.3 (2)
C9—C10—C11—C12	−174.86 (14)	N2—C16—O6—C17	173.11 (13)
C10—C11—C12—C13	−0.2 (3)	C20—C17—O6—C16	−63.8 (2)
C11—C12—C13—C14	0.0 (3)	C19—C17—O6—C16	61.7 (2)
C12—C13—C14—C15	0.3 (3)	C18—C17—O6—C16	178.78 (18)
C11—C10—C15—C14	0.0 (2)	C27—C28—O7—C31	5.1 (3)
C9—C10—C15—C14	174.93 (14)	C29—C28—O7—C31	−175.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O2	0.843 (17)	2.399 (16)	2.6825 (14)	100 (1)
N2—H1N···O4	0.843 (17)	2.317 (17)	2.7811 (15)	115 (1)
C11—H11···O2	0.93	2.39	2.7521 (19)	103
C13—H13···O1^i	0.93	2.42	3.331 (2)	166
C15—H15···O3	0.93	2.37	2.815 (2)	109
C31—H31C···O1^ii	0.96	2.54	3.195 (2)	126

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

(IV) Methyl 2-[(anthracen-9-yl)methoxy]-2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-phenylacetate

Crystal data

C38H36N2O6	F(000) = 1304
Mr = 616.69	Dx = 1.239 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 18.2606 (17) Å	Cell parameters from 9964 reflections
b = 9.8976 (9) Å	θ = 2.4–26.0°
c = 18.5364 (17) Å	µ = 0.08 mm^−1
β = 99.310 (2)°	T = 294 K
V = 3306.1 (5) Å^3	Block, colourless
Z = 4	0.21 × 0.18 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5464 reflections with I > 2σ(I)
ω scans	Rint = 0.026
Absorption correction: multi-scan (SADABS; Bruker, 2001)	θmax = 28.5°, θmin = 1.7°
Tmin = 0.91, Tmax = 0.98	h = −24→24
37911 measured reflections	k = −13→13
8035 independent reflections	l = −24→24

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0564P)^2 + 0.6394P] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
8035 reflections	Δρmax = 0.20 e Å^−3
424 parameters	Δρmin = −0.16 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
C1	−0.05268 (7)	0.10353 (13)	0.76374 (7)	0.0422 (3)
C2	−0.04237 (7)	0.01261 (13)	0.70078 (7)	0.0452 (3)
C3	0.01816 (9)	−0.00926 (17)	0.66735 (8)	0.0590 (4)
H3	0.0627	0.0351	0.6834	0.071*
C4	0.01186 (11)	−0.0986 (2)	0.60929 (9)	0.0807 (6)
H4	0.0524	−0.1139	0.5858	0.097*
C5	−0.05331 (13)	−0.1643 (2)	0.58632 (11)	0.0888 (6)
H5	−0.0560	−0.2258	0.5480	0.107*
C6	−0.11577 (11)	−0.14203 (18)	0.61842 (10)	0.0783 (5)
H6	−0.1602	−0.1866	0.6022	0.094*
C7	−0.10916 (8)	−0.05075 (14)	0.67555 (8)	0.0534 (3)
C8	−0.13768 (8)	0.09427 (15)	0.76291 (8)	0.0513 (3)
C9	−0.01294 (7)	0.04250 (13)	0.83936 (6)	0.0417 (3)
C10	−0.03078 (7)	−0.10834 (14)	0.84224 (7)	0.0456 (3)
C11	0.01814 (8)	−0.20084 (15)	0.82031 (8)	0.0531 (3)
H11	0.0633	−0.1709	0.8091	0.064*
C12	0.00099 (11)	−0.33699 (17)	0.81478 (10)	0.0696 (4)
H12	0.0347	−0.3975	0.8001	0.084*
C13	−0.06495 (12)	−0.38294 (18)	0.83070 (11)	0.0809 (5)
H13	−0.0767	−0.4743	0.8264	0.097*
C14	−0.11347 (11)	−0.29317 (19)	0.85308 (12)	0.0823 (5)
H14	−0.1582	−0.3245	0.8645	0.099*
C15	−0.09741 (9)	−0.15695 (16)	0.85909 (9)	0.0630 (4)
H15	−0.1312	−0.0976	0.8744	0.076*
C16	−0.04542 (8)	0.32138 (14)	0.69828 (7)	0.0505 (3)
C17	−0.13334 (10)	0.33824 (19)	0.58402 (9)	0.0700 (5)
C18	−0.19435 (17)	0.2428 (3)	0.55247 (15)	0.1491 (13)
H18A	−0.2312	0.2395	0.5839	0.224*
H18B	−0.1741	0.1541	0.5485	0.224*
H18C	−0.2166	0.2738	0.5049	0.224*
C19	−0.16193 (17)	0.4772 (3)	0.59570 (15)	0.1295 (10)
H19A	−0.1215	0.5340	0.6169	0.194*
H19B	−0.1979	0.4723	0.6281	0.194*
H19C	−0.1847	0.5143	0.5496	0.194*
C20	−0.07285 (14)	0.3400 (3)	0.53837 (11)	0.1228 (10)
H20A	−0.0501	0.2524	0.5395	0.184*
H20B	−0.0363	0.4060	0.5574	0.184*
H20C	−0.0934	0.3628	0.4889	0.184*
C21	−0.03604 (8)	0.12176 (15)	0.90443 (7)	0.0514 (3)
C22	−0.02619 (17)	0.3288 (2)	0.96664 (11)	0.1138 (9)
H22A	−0.0098	0.2851	1.0126	0.171*
H22B	−0.0789	0.3418	0.9602	0.171*
H22C	−0.0020	0.4149	0.9660	0.171*
C23	−0.23985 (9)	−0.0538 (2)	0.70383 (13)	0.0920 (6)
H23A	−0.2675	−0.0051	0.7353	0.138*
H23B	−0.2398	−0.1482	0.7155	0.138*
H23C	−0.2624	−0.0408	0.6538	0.138*
C24	0.11319 (7)	0.03870 (16)	0.90551 (7)	0.0512 (3)
H24A	0.0992	−0.0442	0.9277	0.061*
H24B	0.1107	0.1123	0.9396	0.061*
C25	0.19027 (8)	0.02670 (16)	0.88784 (7)	0.0525 (3)
C26	0.23039 (8)	−0.09498 (18)	0.89909 (8)	0.0598 (4)
C27	0.20399 (11)	−0.2129 (2)	0.93018 (10)	0.0762 (5)
H27	0.1575	−0.2113	0.9446	0.091*
C28	0.24505 (14)	−0.3280 (2)	0.93934 (13)	0.0981 (7)
H28	0.2264	−0.4039	0.9599	0.118*
C29	0.31581 (14)	−0.3333 (3)	0.91787 (14)	0.1056 (8)
H29	0.3432	−0.4128	0.9238	0.127*
C30	0.34358 (12)	−0.2249 (3)	0.88925 (13)	0.0942 (7)
H30	0.3904	−0.2299	0.8757	0.113*
C31	0.30336 (9)	−0.1020 (2)	0.87904 (9)	0.0717 (5)
C32	0.33211 (10)	0.0113 (2)	0.84921 (10)	0.0797 (6)
H32	0.3791	0.0058	0.8360	0.096*
C33	0.29364 (9)	0.1313 (2)	0.83839 (8)	0.0695 (5)
C34	0.32316 (12)	0.2481 (3)	0.80696 (11)	0.0897 (7)
H34	0.3694	0.2425	0.7923	0.108*
C35	0.28580 (14)	0.3644 (3)	0.79837 (12)	0.0987 (7)
H35	0.3060	0.4383	0.7776	0.118*
C36	0.21624 (12)	0.3755 (2)	0.82044 (10)	0.0851 (6)
H36	0.1911	0.4576	0.8151	0.102*
C37	0.18491 (10)	0.26813 (18)	0.84952 (9)	0.0673 (4)
H37	0.1386	0.2781	0.8636	0.081*
C38	0.22149 (8)	0.14045 (17)	0.85886 (7)	0.0575 (4)
N1	−0.16420 (6)	−0.00414 (13)	0.71419 (7)	0.0573 (3)
N2	−0.02680 (8)	0.24055 (12)	0.75727 (6)	0.0524 (3)
H1N	0.0148 (10)	0.2618 (17)	0.7860 (10)	0.068 (5)*
O1	−0.17264 (6)	0.15827 (12)	0.80133 (7)	0.0724 (3)
O2	0.06347 (5)	0.06437 (9)	0.83747 (4)	0.0449 (2)
O3	−0.07163 (8)	0.07807 (13)	0.94743 (6)	0.0787 (4)
O4	−0.00780 (7)	0.24566 (11)	0.90814 (6)	0.0707 (3)
O5	−0.01139 (7)	0.42241 (12)	0.68892 (7)	0.0767 (4)
O6	−0.10566 (6)	0.27505 (11)	0.65522 (5)	0.0614 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0437 (7)	0.0423 (7)	0.0398 (6)	0.0005 (5)	0.0043 (5)	0.0014 (5)
C2	0.0471 (7)	0.0479 (7)	0.0387 (6)	0.0026 (6)	0.0006 (5)	0.0019 (5)
C3	0.0578 (9)	0.0751 (10)	0.0438 (7)	0.0065 (8)	0.0067 (6)	−0.0011 (7)
C4	0.0813 (12)	0.1069 (15)	0.0537 (9)	0.0209 (11)	0.0105 (9)	−0.0171 (10)
C5	0.0992 (15)	0.0946 (14)	0.0667 (11)	0.0226 (12)	−0.0042 (10)	−0.0323 (10)
C6	0.0792 (12)	0.0681 (11)	0.0763 (11)	−0.0027 (9)	−0.0215 (9)	−0.0166 (9)
C7	0.0522 (8)	0.0488 (8)	0.0545 (8)	0.0029 (6)	−0.0056 (6)	0.0005 (6)
C8	0.0467 (7)	0.0511 (8)	0.0557 (8)	0.0099 (6)	0.0067 (6)	0.0099 (6)
C9	0.0408 (7)	0.0472 (7)	0.0372 (6)	0.0022 (5)	0.0071 (5)	0.0015 (5)
C10	0.0464 (7)	0.0469 (7)	0.0427 (7)	0.0021 (6)	0.0050 (5)	0.0050 (5)
C11	0.0553 (8)	0.0524 (8)	0.0509 (8)	0.0042 (6)	0.0066 (6)	−0.0014 (6)
C12	0.0825 (12)	0.0530 (9)	0.0715 (10)	0.0095 (8)	0.0065 (9)	−0.0060 (8)
C13	0.0961 (14)	0.0504 (10)	0.0941 (14)	−0.0114 (10)	0.0086 (11)	0.0025 (9)
C14	0.0764 (12)	0.0660 (11)	0.1074 (15)	−0.0173 (10)	0.0235 (11)	0.0112 (10)
C15	0.0564 (9)	0.0579 (9)	0.0769 (10)	0.0007 (7)	0.0181 (8)	0.0109 (8)
C16	0.0625 (9)	0.0442 (7)	0.0448 (7)	0.0005 (6)	0.0092 (6)	0.0007 (6)
C17	0.0773 (11)	0.0789 (11)	0.0500 (9)	0.0096 (9)	−0.0015 (8)	0.0189 (8)
C18	0.144 (2)	0.168 (3)	0.1059 (19)	−0.052 (2)	−0.0699 (18)	0.0542 (19)
C19	0.155 (2)	0.118 (2)	0.1094 (19)	0.0701 (18)	0.0047 (17)	0.0331 (16)
C20	0.1225 (19)	0.199 (3)	0.0493 (10)	0.0272 (19)	0.0205 (12)	0.0167 (14)
C21	0.0585 (8)	0.0547 (8)	0.0413 (7)	0.0114 (7)	0.0092 (6)	0.0016 (6)
C22	0.209 (3)	0.0694 (12)	0.0674 (12)	0.0186 (15)	0.0370 (15)	−0.0217 (10)
C23	0.0463 (9)	0.0976 (15)	0.1256 (17)	−0.0143 (9)	−0.0059 (10)	0.0140 (13)
C24	0.0504 (8)	0.0653 (9)	0.0357 (6)	−0.0003 (7)	0.0005 (6)	0.0022 (6)
C25	0.0460 (7)	0.0721 (10)	0.0367 (7)	−0.0033 (7)	−0.0016 (5)	−0.0043 (6)
C26	0.0525 (8)	0.0775 (11)	0.0450 (8)	0.0042 (8)	−0.0050 (6)	−0.0062 (7)
C27	0.0708 (11)	0.0802 (12)	0.0723 (11)	0.0099 (9)	−0.0038 (9)	0.0068 (9)
C28	0.1075 (17)	0.0830 (14)	0.0948 (15)	0.0178 (13)	−0.0106 (13)	0.0065 (12)
C29	0.0950 (17)	0.1087 (19)	0.1020 (17)	0.0434 (15)	−0.0173 (13)	−0.0183 (15)
C30	0.0700 (13)	0.1208 (19)	0.0859 (14)	0.0277 (13)	−0.0052 (10)	−0.0218 (14)
C31	0.0526 (9)	0.1034 (14)	0.0541 (9)	0.0106 (9)	−0.0065 (7)	−0.0192 (9)
C32	0.0469 (9)	0.1326 (18)	0.0585 (10)	−0.0086 (11)	0.0052 (7)	−0.0191 (11)
C33	0.0524 (9)	0.1074 (14)	0.0470 (8)	−0.0179 (10)	0.0026 (7)	−0.0093 (9)
C34	0.0671 (12)	0.139 (2)	0.0633 (11)	−0.0410 (13)	0.0108 (9)	−0.0007 (12)
C35	0.0917 (16)	0.123 (2)	0.0758 (13)	−0.0483 (15)	−0.0029 (11)	0.0200 (13)
C36	0.0904 (14)	0.0853 (13)	0.0715 (11)	−0.0284 (11)	−0.0115 (10)	0.0115 (10)
C37	0.0642 (10)	0.0780 (11)	0.0547 (9)	−0.0162 (9)	−0.0053 (7)	0.0022 (8)
C38	0.0507 (8)	0.0799 (11)	0.0386 (7)	−0.0140 (7)	−0.0027 (6)	−0.0037 (7)
N1	0.0414 (6)	0.0566 (7)	0.0700 (8)	−0.0031 (5)	−0.0022 (6)	0.0056 (6)
N2	0.0628 (8)	0.0475 (7)	0.0431 (6)	−0.0083 (6)	−0.0023 (6)	0.0040 (5)
O1	0.0629 (7)	0.0800 (8)	0.0772 (8)	0.0255 (6)	0.0198 (6)	0.0042 (6)
O2	0.0420 (5)	0.0572 (6)	0.0346 (4)	−0.0035 (4)	0.0033 (4)	0.0017 (4)
O3	0.1020 (9)	0.0863 (8)	0.0566 (6)	0.0013 (7)	0.0399 (7)	−0.0012 (6)
O4	0.1091 (9)	0.0539 (6)	0.0511 (6)	0.0001 (6)	0.0190 (6)	−0.0112 (5)
O5	0.0986 (9)	0.0564 (7)	0.0706 (7)	−0.0185 (6)	0.0004 (6)	0.0140 (6)
O6	0.0664 (7)	0.0629 (6)	0.0500 (6)	−0.0039 (5)	−0.0051 (5)	0.0153 (5)

Geometric parameters (Å, º)

C1—N2	1.4475 (17)	C20—H20A	0.9600
C1—C2	1.5094 (18)	C20—H20B	0.9600
C1—C8	1.5525 (19)	C20—H20C	0.9600
C1—C9	1.5896 (17)	C21—O3	1.1884 (17)
C2—C3	1.369 (2)	C21—O4	1.3278 (18)
C2—C7	1.3838 (19)	C22—O4	1.444 (2)
C3—C4	1.383 (2)	C22—H22A	0.9600
C3—H3	0.9300	C22—H22B	0.9600
C4—C5	1.363 (3)	C22—H22C	0.9600
C4—H4	0.9300	C23—N1	1.4492 (19)
C5—C6	1.387 (3)	C23—H23A	0.9600
C5—H5	0.9300	C23—H23B	0.9600
C6—C7	1.382 (2)	C23—H23C	0.9600
C6—H6	0.9300	C24—O2	1.4523 (15)
C7—N1	1.403 (2)	C24—C25	1.5005 (19)
C8—O1	1.2096 (17)	C24—H24A	0.9700
C8—N1	1.3628 (19)	C24—H24B	0.9700
C9—O2	1.4180 (15)	C25—C26	1.408 (2)
C9—C10	1.5308 (19)	C25—C38	1.407 (2)
C9—C21	1.5534 (18)	C26—C27	1.420 (3)
C10—C11	1.3852 (19)	C26—C31	1.442 (2)
C10—C15	1.390 (2)	C27—C28	1.360 (3)
C11—C12	1.383 (2)	C27—H27	0.9300
C11—H11	0.9300	C28—C29	1.413 (3)
C12—C13	1.363 (3)	C28—H28	0.9300
C12—H12	0.9300	C29—C30	1.333 (3)
C13—C14	1.366 (3)	C29—H29	0.9300
C13—H13	0.9300	C30—C31	1.417 (3)
C14—C15	1.381 (2)	C30—H30	0.9300
C14—H14	0.9300	C31—C32	1.390 (3)
C15—H15	0.9300	C32—C33	1.379 (3)
C16—O5	1.2046 (17)	C32—H32	0.9300
C16—O6	1.3317 (18)	C33—C38	1.432 (2)
C16—N2	1.3531 (18)	C33—C34	1.438 (3)
C17—O6	1.4740 (18)	C34—C35	1.334 (3)
C17—C20	1.496 (3)	C34—H34	0.9300
C17—C19	1.499 (3)	C35—C36	1.400 (3)
C17—C18	1.505 (3)	C35—H35	0.9300
C18—H18A	0.9600	C36—C37	1.359 (2)
C18—H18B	0.9600	C36—H36	0.9300
C18—H18C	0.9600	C37—C38	1.427 (2)
C19—H19A	0.9600	C37—H37	0.9300
C19—H19B	0.9600	N2—H1N	0.880 (18)
C19—H19C	0.9600
N2—C1—C2	114.29 (11)	C17—C20—H20C	109.5
N2—C1—C8	113.19 (11)	H20A—C20—H20C	109.5
C2—C1—C8	101.92 (11)	H20B—C20—H20C	109.5
N2—C1—C9	108.69 (10)	O3—C21—O4	123.45 (14)
C2—C1—C9	111.03 (10)	O3—C21—C9	125.72 (14)
C8—C1—C9	107.42 (10)	O4—C21—C9	110.77 (12)
C3—C2—C7	120.50 (13)	O4—C22—H22A	109.5
C3—C2—C1	130.91 (13)	O4—C22—H22B	109.5
C7—C2—C1	108.55 (12)	H22A—C22—H22B	109.5
C2—C3—C4	118.79 (16)	O4—C22—H22C	109.5
C2—C3—H3	120.6	H22A—C22—H22C	109.5
C4—C3—H3	120.6	H22B—C22—H22C	109.5
C5—C4—C3	120.45 (17)	N1—C23—H23A	109.5
C5—C4—H4	119.8	N1—C23—H23B	109.5
C3—C4—H4	119.8	H23A—C23—H23B	109.5
C4—C5—C6	121.83 (17)	N1—C23—H23C	109.5
C4—C5—H5	119.1	H23A—C23—H23C	109.5
C6—C5—H5	119.1	H23B—C23—H23C	109.5
C7—C6—C5	117.18 (17)	O2—C24—C25	107.52 (10)
C7—C6—H6	121.4	O2—C24—H24A	110.2
C5—C6—H6	121.4	C25—C24—H24A	110.2
C2—C7—C6	121.19 (15)	O2—C24—H24B	110.2
C2—C7—N1	110.09 (12)	C25—C24—H24B	110.2
C6—C7—N1	128.68 (15)	H24A—C24—H24B	108.5
O1—C8—N1	126.85 (14)	C26—C25—C38	120.51 (14)
O1—C8—C1	125.82 (14)	C26—C25—C24	121.31 (14)
N1—C8—C1	107.24 (12)	C38—C25—C24	118.18 (14)
O2—C9—C10	111.44 (10)	C25—C26—C27	124.09 (15)
O2—C9—C21	109.51 (10)	C25—C26—C31	118.94 (16)
C10—C9—C21	112.29 (11)	C27—C26—C31	116.97 (16)
O2—C9—C1	103.35 (9)	C28—C27—C26	121.5 (2)
C10—C9—C1	109.39 (10)	C28—C27—H27	119.2
C21—C9—C1	110.50 (10)	C26—C27—H27	119.2
C11—C10—C15	117.81 (14)	C27—C28—C29	120.4 (2)
C11—C10—C9	118.90 (12)	C27—C28—H28	119.8
C15—C10—C9	122.98 (12)	C29—C28—H28	119.8
C12—C11—C10	121.10 (15)	C30—C29—C28	120.4 (2)
C12—C11—H11	119.4	C30—C29—H29	119.8
C10—C11—H11	119.4	C28—C29—H29	119.8
C13—C12—C11	120.40 (17)	C29—C30—C31	121.4 (2)
C13—C12—H12	119.8	C29—C30—H30	119.3
C11—C12—H12	119.8	C31—C30—H30	119.3
C12—C13—C14	119.20 (17)	C32—C31—C30	121.61 (19)
C12—C13—H13	120.4	C32—C31—C26	119.19 (17)
C14—C13—H13	120.4	C30—C31—C26	119.2 (2)
C13—C14—C15	121.33 (17)	C33—C32—C31	122.47 (16)
C13—C14—H14	119.3	C33—C32—H32	118.8
C15—C14—H14	119.3	C31—C32—H32	118.8
C14—C15—C10	120.15 (16)	C32—C33—C38	119.01 (17)
C14—C15—H15	119.9	C32—C33—C34	122.43 (18)
C10—C15—H15	119.9	C38—C33—C34	118.6 (2)
O5—C16—O6	126.50 (13)	C35—C34—C33	121.6 (2)
O5—C16—N2	122.63 (14)	C35—C34—H34	119.2
O6—C16—N2	110.85 (12)	C33—C34—H34	119.2
O6—C17—C20	109.50 (15)	C34—C35—C36	120.2 (2)
O6—C17—C19	109.69 (16)	C34—C35—H35	119.9
C20—C17—C19	112.2 (2)	C36—C35—H35	119.9
O6—C17—C18	101.93 (15)	C37—C36—C35	120.9 (2)
C20—C17—C18	110.8 (2)	C37—C36—H36	119.5
C19—C17—C18	112.3 (2)	C35—C36—H36	119.5
C17—C18—H18A	109.5	C36—C37—C38	121.45 (18)
C17—C18—H18B	109.5	C36—C37—H37	119.3
H18A—C18—H18B	109.5	C38—C37—H37	119.3
C17—C18—H18C	109.5	C25—C38—C37	122.97 (14)
H18A—C18—H18C	109.5	C25—C38—C33	119.85 (16)
H18B—C18—H18C	109.5	C37—C38—C33	117.17 (16)
C17—C19—H19A	109.5	C8—N1—C7	111.47 (12)
C17—C19—H19B	109.5	C8—N1—C23	123.98 (15)
H19A—C19—H19B	109.5	C7—N1—C23	124.55 (15)
C17—C19—H19C	109.5	C16—N2—C1	125.32 (12)
H19A—C19—H19C	109.5	C16—N2—H1N	115.3 (11)
H19B—C19—H19C	109.5	C1—N2—H1N	115.8 (11)
C17—C20—H20A	109.5	C9—O2—C24	115.55 (9)
C17—C20—H20B	109.5	C21—O4—C22	115.47 (15)
H20A—C20—H20B	109.5	C16—O6—C17	121.39 (12)
N2—C1—C2—C3	48.42 (19)	C38—C25—C26—C31	−1.3 (2)
C8—C1—C2—C3	170.89 (14)	C24—C25—C26—C31	178.11 (12)
C9—C1—C2—C3	−74.97 (18)	C25—C26—C27—C28	179.58 (17)
N2—C1—C2—C7	−129.31 (12)	C31—C26—C27—C28	−1.2 (3)
C8—C1—C2—C7	−6.84 (14)	C26—C27—C28—C29	0.0 (3)
C9—C1—C2—C7	107.31 (12)	C27—C28—C29—C30	0.9 (3)
C7—C2—C3—C4	−1.8 (2)	C28—C29—C30—C31	−0.4 (3)
C1—C2—C3—C4	−179.27 (15)	C29—C30—C31—C32	180.00 (19)
C2—C3—C4—C5	−0.5 (3)	C29—C30—C31—C26	−0.9 (3)
C3—C4—C5—C6	1.7 (3)	C25—C26—C31—C32	0.0 (2)
C4—C5—C6—C7	−0.6 (3)	C27—C26—C31—C32	−179.23 (15)
C3—C2—C7—C6	3.0 (2)	C25—C26—C31—C30	−179.09 (15)
C1—C2—C7—C6	−179.02 (14)	C27—C26—C31—C30	1.7 (2)
C3—C2—C7—N1	−174.99 (13)	C30—C31—C32—C33	179.55 (16)
C1—C2—C7—N1	3.02 (16)	C26—C31—C32—C33	0.5 (2)
C5—C6—C7—C2	−1.8 (3)	C31—C32—C33—C38	0.3 (2)
C5—C6—C7—N1	175.78 (16)	C31—C32—C33—C34	−179.47 (16)
N2—C1—C8—O1	−51.72 (18)	C32—C33—C34—C35	−178.53 (19)
C2—C1—C8—O1	−174.93 (14)	C38—C33—C34—C35	1.7 (3)
C9—C1—C8—O1	68.27 (17)	C33—C34—C35—C36	0.3 (3)
N2—C1—C8—N1	131.69 (12)	C34—C35—C36—C37	−1.3 (3)
C2—C1—C8—N1	8.47 (13)	C35—C36—C37—C38	0.1 (3)
C9—C1—C8—N1	−108.33 (12)	C26—C25—C38—C37	−176.94 (13)
N2—C1—C9—O2	−52.99 (12)	C24—C25—C38—C37	3.7 (2)
C2—C1—C9—O2	73.55 (12)	C26—C25—C38—C33	2.0 (2)
C8—C1—C9—O2	−175.80 (10)	C24—C25—C38—C33	−177.35 (12)
N2—C1—C9—C10	−171.80 (10)	C36—C37—C38—C25	−179.12 (15)
C2—C1—C9—C10	−45.26 (14)	C36—C37—C38—C33	1.9 (2)
C8—C1—C9—C10	65.39 (13)	C32—C33—C38—C25	−1.5 (2)
N2—C1—C9—C21	64.09 (14)	C34—C33—C38—C25	178.22 (14)
C2—C1—C9—C21	−169.37 (11)	C32—C33—C38—C37	177.49 (14)
C8—C1—C9—C21	−58.72 (14)	C34—C33—C38—C37	−2.7 (2)
O2—C9—C10—C11	−19.77 (16)	O1—C8—N1—C7	176.15 (14)
C21—C9—C10—C11	−143.05 (12)	C1—C8—N1—C7	−7.30 (15)
C1—C9—C10—C11	93.88 (14)	O1—C8—N1—C23	−3.8 (2)
O2—C9—C10—C15	166.72 (12)	C1—C8—N1—C23	172.78 (14)
C21—C9—C10—C15	43.44 (18)	C2—C7—N1—C8	2.89 (17)
C1—C9—C10—C15	−79.62 (16)	C6—C7—N1—C8	−174.87 (16)
C15—C10—C11—C12	0.5 (2)	C2—C7—N1—C23	−177.19 (15)
C9—C10—C11—C12	−173.34 (14)	C6—C7—N1—C23	5.0 (3)
C10—C11—C12—C13	0.2 (3)	O5—C16—N2—C1	−164.10 (14)
C11—C12—C13—C14	−0.8 (3)	O6—C16—N2—C1	17.3 (2)
C12—C13—C14—C15	0.7 (3)	C2—C1—N2—C16	51.43 (19)
C13—C14—C15—C10	0.0 (3)	C8—C1—N2—C16	−64.67 (18)
C11—C10—C15—C14	−0.6 (2)	C9—C1—N2—C16	176.07 (13)
C9—C10—C15—C14	172.96 (15)	C10—C9—O2—C24	−72.54 (13)
O2—C9—C21—O3	−133.23 (15)	C21—C9—O2—C24	52.31 (14)
C10—C9—C21—O3	−8.9 (2)	C1—C9—O2—C24	170.08 (10)
C1—C9—C21—O3	113.56 (16)	C25—C24—O2—C9	163.50 (11)
O2—C9—C21—O4	44.04 (15)	O3—C21—O4—C22	−3.0 (2)
C10—C9—C21—O4	168.39 (11)	C9—C21—O4—C22	179.66 (15)
C1—C9—C21—O4	−69.17 (14)	O5—C16—O6—C17	7.1 (2)
O2—C24—C25—C26	−116.16 (14)	N2—C16—O6—C17	−174.43 (13)
O2—C24—C25—C38	63.22 (16)	C20—C17—O6—C16	55.8 (2)
C38—C25—C26—C27	177.91 (14)	C19—C17—O6—C16	−67.7 (2)
C24—C25—C26—C27	−2.7 (2)	C18—C17—O6—C16	173.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O2	0.880 (18)	2.289 (17)	2.6786 (15)	107 (1)
N2—H1N···O4	0.880 (18)	2.371 (17)	2.7622 (16)	107 (1)
C11—H11···O2	0.93	2.39	2.7553 (18)	103
C15—H15···O3	0.93	2.36	2.840 (2)	112
C23—H23B···O1^i	0.96	2.48	3.262 (2)	138
C24—H24A···O3^ii	0.97	2.47	3.1641 (18)	128

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