3-{4-[4-(3-Oxo-1,3-dihydro­isobenzofuran-1-ylamino)benz­yl]phenyl­amino}isobenzofuran-1(3H)-one dimethyl­formamide solvate

The crystal structure of the title compound, C₂₉H₂₂N₂O₄·C₃H₇NO, is stabilized by two N—H...O and six C—H...O inter­molecular hydrogen bonds and C—H...π and π–π inter­actions. The inter­molecular hydrogen bonds generate R₁²(6) and R₂²(32) ring motifs.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.072
• wR factor = 0.203
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.101
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.71 mm
PLAT223_ALERT_4_C Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       3.20 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N3
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C35
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT480_ALERT_4_C Long H...A H-Bond Reported H34    ..  O5      ..       2.81 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8     ..  O1      ..       2.88 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H36B   ..  O3      ..       2.85 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.845(18) ......       2.22 su-Ra
              N2   -H2      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.845(18) ......       2.22 su-Ra
              N2   -H2      1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-{4-[4-(3-Oxo-1,3-dihydroisobenzofuran-1- ylamino)benzyl]phenylamino}isobenzofuran-1(3H)-one dimethylformamide solvate

Crystal data

C29H22N2O4·C3H7NO	Z = 2
Mr = 535.58	F(000) = 564
Triclinic, P1	Dx = 1.287 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0267 (7) Å	Cell parameters from 13625 reflections
b = 12.6709 (11) Å	θ = 2.0–27.9°
c = 14.6529 (13) Å	µ = 0.09 mm^−1
α = 98.911 (7)°	T = 296 K
β = 100.893 (7)°	Long prismatic stick, light brown
γ = 104.746 (6)°	0.71 × 0.34 × 0.11 mm
V = 1382.5 (2) Å^3

Data collection

Stoe IPDS-2 diffractometer	5014 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2712 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.101
Detector resolution: 6.67 pixels mm^-1	θmax = 25.3°, θmin = 2.0°
ω scans	h = −9→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −15→15
Tmin = 0.951, Tmax = 0.988	l = −17→17
16524 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.203	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.1127P)^2] where P = (Fo^2 + 2Fc^2)/3
5014 reflections	(Δ/σ)max < 0.001
371 parameters	Δρmax = 0.41 e Å^−3
2 restraints	Δρmin = −0.34 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.0074 (5)	0.9750 (4)	0.8705 (3)	0.0632 (10)
C2	−0.1747 (5)	0.9633 (3)	0.8757 (2)	0.0551 (9)
C3	−0.2809 (6)	1.0314 (4)	0.8541 (3)	0.0727 (12)
H3	−0.2378	1.0970	0.8340	0.087*
C4	−0.4514 (7)	0.9978 (4)	0.8637 (3)	0.0832 (14)
H4	−0.5258	1.0418	0.8502	0.100*
C5	−0.5164 (6)	0.8995 (4)	0.8934 (3)	0.0770 (12)
H5	−0.6331	0.8786	0.8990	0.092*
C6	−0.4101 (5)	0.8330 (4)	0.9142 (3)	0.0660 (10)
H6	−0.4533	0.7670	0.9338	0.079*
C7	−0.2383 (5)	0.8664 (3)	0.9056 (2)	0.0526 (9)
C8	−0.0949 (5)	0.8093 (3)	0.9207 (3)	0.0527 (9)
H8	−0.0595	0.8093	0.9885	0.063*
C9	−0.0459 (4)	0.6256 (3)	0.8789 (2)	0.0484 (8)
C10	0.1162 (5)	0.6518 (3)	0.9438 (3)	0.0541 (9)
H10	0.1656	0.7231	0.9821	0.065*
C11	0.2052 (5)	0.5713 (3)	0.9518 (2)	0.0551 (9)
H11	0.3133	0.5897	0.9960	0.066*
C12	0.1371 (5)	0.4656 (3)	0.8962 (2)	0.0509 (8)
C13	−0.0241 (5)	0.4402 (3)	0.8314 (3)	0.0608 (10)
H13	−0.0724	0.3691	0.7926	0.073*
C14	−0.1143 (5)	0.5190 (3)	0.8235 (3)	0.0553 (9)
H14	−0.2234	0.4998	0.7800	0.066*
C15	0.2365 (6)	0.3789 (3)	0.9027 (3)	0.0638 (10)
H15A	0.3246	0.4020	0.9628	0.077*
H15B	0.1534	0.3086	0.9033	0.077*
C21	0.5116 (5)	0.3352 (3)	0.3846 (3)	0.0585 (9)
C22	0.6984 (5)	0.3360 (3)	0.3985 (2)	0.0522 (9)
C23	0.7979 (6)	0.3207 (3)	0.3330 (3)	0.0684 (11)
H23	0.7490	0.3078	0.2680	0.082*
C24	0.9702 (6)	0.3250 (4)	0.3669 (3)	0.0742 (12)
H24	1.0402	0.3150	0.3243	0.089*
C25	1.0433 (5)	0.3441 (3)	0.4640 (3)	0.0675 (11)
H25	1.1607	0.3453	0.4852	0.081*
C26	0.9449 (5)	0.3612 (3)	0.5290 (3)	0.0587 (9)
H26	0.9943	0.3751	0.5940	0.070*
C27	0.7701 (4)	0.3572 (3)	0.4949 (2)	0.0474 (8)
C28	0.6346 (4)	0.3745 (3)	0.5479 (2)	0.0490 (8)
H28	0.6720	0.4518	0.5842	0.059*
C29	0.5032 (4)	0.3193 (3)	0.6772 (2)	0.0450 (8)
C30	0.4168 (5)	0.4006 (3)	0.6811 (3)	0.0540 (9)
H30	0.4150	0.4424	0.6342	0.065*
C31	0.3334 (5)	0.4209 (3)	0.7528 (3)	0.0545 (9)
H31	0.2786	0.4774	0.7540	0.065*
C32	0.3283 (4)	0.3596 (3)	0.8235 (2)	0.0472 (8)
C33	0.4110 (5)	0.2756 (3)	0.8170 (3)	0.0554 (9)
H33	0.4072	0.2309	0.8618	0.066*
C34	0.4978 (5)	0.2564 (3)	0.7469 (3)	0.0534 (9)
H34	0.5539	0.2006	0.7460	0.064*
C35	0.9305 (9)	0.1156 (5)	0.6487 (4)	0.1014 (17)
H35	1.0429	0.1667	0.6704	0.122*
C36	0.7810 (17)	−0.0745 (10)	0.5933 (8)	0.261 (8)
H36A	0.6758	−0.0510	0.5809	0.391*
H36B	0.7773	−0.1160	0.6428	0.391*
H36C	0.7874	−0.1209	0.5365	0.391*
C37	1.0992 (14)	−0.0147 (8)	0.6295 (6)	0.186 (4)
H37A	1.1946	0.0521	0.6376	0.279*
H37B	1.0937	−0.0664	0.5729	0.279*
H37C	1.1191	−0.0480	0.6835	0.279*
N1	−0.1462 (4)	0.7006 (3)	0.8689 (2)	0.0571 (8)
N2	0.5983 (4)	0.3019 (3)	0.6088 (2)	0.0541 (8)
N3	0.9228 (9)	0.0146 (5)	0.6205 (4)	0.1229 (18)
O1	0.1114 (4)	1.0504 (3)	0.8516 (3)	0.0931 (10)
O2	0.0531 (3)	0.8848 (2)	0.89352 (19)	0.0637 (7)
O3	0.4012 (4)	0.3188 (3)	0.3116 (2)	0.0853 (9)
O4	0.4745 (3)	0.3572 (2)	0.46952 (18)	0.0593 (7)
O5	0.8055 (8)	0.1518 (5)	0.6499 (4)	0.165 (2)
H1	−0.221 (5)	0.685 (3)	0.8137 (19)	0.077 (13)*
H2	0.653 (5)	0.253 (3)	0.610 (3)	0.062 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.064 (2)	0.063 (3)	0.059 (2)	0.013 (2)	0.0103 (18)	0.0188 (19)
C2	0.061 (2)	0.058 (2)	0.0501 (19)	0.0245 (18)	0.0124 (16)	0.0124 (17)
C3	0.081 (3)	0.069 (3)	0.076 (3)	0.035 (2)	0.014 (2)	0.023 (2)
C4	0.093 (4)	0.090 (4)	0.082 (3)	0.058 (3)	0.014 (3)	0.018 (3)
C5	0.063 (3)	0.096 (4)	0.083 (3)	0.041 (3)	0.023 (2)	0.014 (3)
C6	0.060 (2)	0.077 (3)	0.071 (3)	0.030 (2)	0.0238 (19)	0.019 (2)
C7	0.055 (2)	0.061 (2)	0.0454 (19)	0.0257 (18)	0.0121 (15)	0.0087 (17)
C8	0.053 (2)	0.058 (2)	0.0502 (19)	0.0204 (18)	0.0115 (16)	0.0147 (17)
C9	0.0462 (18)	0.056 (2)	0.0477 (18)	0.0211 (17)	0.0121 (15)	0.0143 (17)
C10	0.0486 (19)	0.052 (2)	0.056 (2)	0.0157 (17)	0.0033 (16)	0.0035 (16)
C11	0.0476 (19)	0.070 (3)	0.050 (2)	0.0240 (18)	0.0069 (15)	0.0127 (18)
C12	0.056 (2)	0.059 (2)	0.0478 (19)	0.0250 (18)	0.0189 (16)	0.0183 (17)
C13	0.063 (2)	0.056 (2)	0.059 (2)	0.0177 (19)	0.0107 (18)	0.0048 (18)
C14	0.0465 (19)	0.059 (2)	0.054 (2)	0.0169 (17)	0.0010 (15)	0.0051 (18)
C15	0.079 (3)	0.071 (3)	0.062 (2)	0.041 (2)	0.027 (2)	0.029 (2)
C21	0.057 (2)	0.061 (2)	0.057 (2)	0.0187 (18)	0.0040 (18)	0.0213 (18)
C22	0.058 (2)	0.052 (2)	0.051 (2)	0.0212 (17)	0.0136 (16)	0.0164 (16)
C23	0.087 (3)	0.068 (3)	0.060 (2)	0.030 (2)	0.027 (2)	0.019 (2)
C24	0.077 (3)	0.078 (3)	0.089 (3)	0.035 (2)	0.046 (2)	0.028 (2)
C25	0.049 (2)	0.069 (3)	0.096 (3)	0.025 (2)	0.027 (2)	0.027 (2)
C26	0.048 (2)	0.065 (3)	0.067 (2)	0.0197 (18)	0.0117 (17)	0.0192 (19)
C27	0.0471 (18)	0.046 (2)	0.054 (2)	0.0177 (15)	0.0142 (15)	0.0162 (16)
C28	0.0418 (17)	0.054 (2)	0.0509 (19)	0.0161 (15)	0.0059 (14)	0.0130 (16)
C29	0.0393 (17)	0.046 (2)	0.0485 (18)	0.0132 (15)	0.0066 (14)	0.0097 (15)
C30	0.058 (2)	0.063 (2)	0.057 (2)	0.0296 (19)	0.0210 (17)	0.0280 (18)
C31	0.058 (2)	0.053 (2)	0.065 (2)	0.0294 (18)	0.0193 (17)	0.0244 (18)
C32	0.0454 (18)	0.052 (2)	0.0487 (18)	0.0195 (15)	0.0109 (14)	0.0146 (15)
C33	0.062 (2)	0.053 (2)	0.061 (2)	0.0231 (18)	0.0169 (18)	0.0267 (18)
C34	0.058 (2)	0.044 (2)	0.066 (2)	0.0244 (17)	0.0164 (18)	0.0182 (17)
C35	0.140 (5)	0.065 (3)	0.111 (4)	0.050 (3)	0.029 (4)	0.021 (3)
C36	0.315 (16)	0.179 (10)	0.170 (9)	−0.111 (10)	0.039 (9)	0.022 (8)
C37	0.256 (11)	0.194 (9)	0.152 (7)	0.156 (9)	0.041 (7)	0.023 (6)
N1	0.0571 (18)	0.056 (2)	0.0538 (18)	0.0264 (15)	−0.0036 (14)	0.0035 (15)
N2	0.0562 (18)	0.060 (2)	0.0594 (18)	0.0303 (16)	0.0196 (14)	0.0228 (15)
N3	0.190 (6)	0.079 (3)	0.096 (3)	0.042 (4)	0.026 (3)	0.013 (3)
O1	0.077 (2)	0.091 (2)	0.110 (3)	0.0079 (18)	0.0216 (18)	0.048 (2)
O2	0.0525 (15)	0.0690 (18)	0.0728 (17)	0.0204 (13)	0.0142 (12)	0.0211 (14)
O3	0.0763 (19)	0.105 (2)	0.0672 (18)	0.0267 (17)	−0.0084 (15)	0.0268 (17)
O4	0.0455 (13)	0.0786 (18)	0.0592 (16)	0.0270 (12)	0.0077 (11)	0.0220 (13)
O5	0.212 (5)	0.176 (5)	0.210 (5)	0.144 (5)	0.112 (4)	0.116 (4)

Geometric parameters (Å, º)

C1—O1	1.204 (5)	C23—C24	1.362 (6)
C1—O2	1.357 (5)	C23—H23	0.9300
C1—C2	1.449 (6)	C24—C25	1.390 (6)
C2—C7	1.375 (5)	C24—H24	0.9300
C2—C3	1.389 (5)	C25—C26	1.373 (6)
C3—C4	1.368 (7)	C25—H25	0.9300
C3—H3	0.9300	C26—C27	1.382 (5)
C4—C5	1.391 (7)	C26—H26	0.9300
C4—H4	0.9300	C27—C28	1.491 (5)
C5—C6	1.370 (5)	C28—N2	1.394 (4)
C5—H5	0.9300	C28—O4	1.497 (4)
C6—C7	1.372 (5)	C28—H28	0.9800
C6—H6	0.9300	C29—C30	1.381 (4)
C7—C8	1.508 (4)	C29—C34	1.389 (5)
C8—N1	1.383 (5)	C29—N2	1.394 (4)
C8—O2	1.485 (4)	C30—C31	1.375 (5)
C8—H8	0.9800	C30—H30	0.9300
C9—C14	1.378 (5)	C31—C32	1.388 (5)
C9—C10	1.386 (5)	C31—H31	0.9300
C9—N1	1.400 (4)	C32—C33	1.391 (5)
C10—C11	1.393 (5)	C33—C34	1.372 (5)
C10—H10	0.9300	C33—H33	0.9300
C11—C12	1.371 (5)	C34—H34	0.9300
C11—H11	0.9300	C35—O5	1.207 (7)
C12—C13	1.381 (5)	C35—N3	1.264 (7)
C12—C15	1.516 (5)	C35—H35	0.9300
C13—C14	1.382 (5)	C36—N3	1.328 (10)
C13—H13	0.9300	C36—H36A	0.9600
C14—H14	0.9300	C36—H36B	0.9600
C15—C32	1.509 (5)	C36—H36C	0.9600
C15—H15A	0.9700	C37—N3	1.540 (10)
C15—H15B	0.9700	C37—H37A	0.9600
C21—O3	1.204 (4)	C37—H37B	0.9600
C21—O4	1.338 (5)	C37—H37C	0.9600
C21—C22	1.471 (5)	N1—H1	0.871 (19)
C22—C27	1.376 (5)	N2—H2	0.845 (18)
C22—C23	1.382 (5)
O1—C1—O2	121.6 (4)	C23—C24—H24	119.4
O1—C1—C2	129.3 (4)	C25—C24—H24	119.4
O2—C1—C2	109.1 (3)	C26—C25—C24	121.0 (4)
C7—C2—C3	121.4 (4)	C26—C25—H25	119.5
C7—C2—C1	108.7 (3)	C24—C25—H25	119.5
C3—C2—C1	129.8 (4)	C25—C26—C27	118.0 (4)
C4—C3—C2	117.1 (4)	C25—C26—H26	121.0
C4—C3—H3	121.5	C27—C26—H26	121.0
C2—C3—H3	121.5	C22—C27—C26	120.4 (3)
C3—C4—C5	121.6 (4)	C22—C27—C28	109.9 (3)
C3—C4—H4	119.2	C26—C27—C28	129.7 (3)
C5—C4—H4	119.2	N2—C28—C27	115.0 (3)
C6—C5—C4	120.7 (4)	N2—C28—O4	111.0 (3)
C6—C5—H5	119.7	C27—C28—O4	102.6 (3)
C4—C5—H5	119.7	N2—C28—H28	109.4
C5—C6—C7	118.2 (4)	C27—C28—H28	109.4
C5—C6—H6	120.9	O4—C28—H28	109.4
C7—C6—H6	120.9	C30—C29—C34	117.5 (3)
C6—C7—C2	121.0 (3)	C30—C29—N2	122.3 (3)
C6—C7—C8	129.8 (4)	C34—C29—N2	120.2 (3)
C2—C7—C8	109.2 (3)	C31—C30—C29	121.2 (3)
N1—C8—O2	113.6 (3)	C31—C30—H30	119.4
N1—C8—C7	113.4 (3)	C29—C30—H30	119.4
O2—C8—C7	102.5 (3)	C30—C31—C32	122.0 (3)
N1—C8—H8	109.1	C30—C31—H31	119.0
O2—C8—H8	109.1	C32—C31—H31	119.0
C7—C8—H8	109.1	C31—C32—C33	116.2 (3)
C14—C9—C10	118.2 (3)	C31—C32—C15	123.3 (3)
C14—C9—N1	118.3 (3)	C33—C32—C15	120.5 (3)
C10—C9—N1	123.5 (3)	C34—C33—C32	122.2 (3)
C9—C10—C11	120.0 (3)	C34—C33—H33	118.9
C9—C10—H10	120.0	C32—C33—H33	118.9
C11—C10—H10	120.0	C33—C34—C29	120.9 (3)
C12—C11—C10	121.6 (3)	C33—C34—H34	119.5
C12—C11—H11	119.2	C29—C34—H34	119.5
C10—C11—H11	119.2	O5—C35—N3	126.0 (7)
C11—C12—C13	118.1 (3)	O5—C35—H35	117.0
C11—C12—C15	121.6 (3)	N3—C35—H35	117.0
C13—C12—C15	120.3 (4)	N3—C36—H36A	109.5
C12—C13—C14	120.8 (4)	N3—C36—H36B	109.5
C12—C13—H13	119.6	H36A—C36—H36B	109.5
C14—C13—H13	119.6	N3—C36—H36C	109.5
C9—C14—C13	121.3 (3)	H36A—C36—H36C	109.5
C9—C14—H14	119.4	H36B—C36—H36C	109.5
C13—C14—H14	119.4	N3—C37—H37A	109.5
C32—C15—C12	115.1 (3)	N3—C37—H37B	109.5
C32—C15—H15A	108.5	H37A—C37—H37B	109.5
C12—C15—H15A	108.5	N3—C37—H37C	109.5
C32—C15—H15B	108.5	H37A—C37—H37C	109.5
C12—C15—H15B	108.5	H37B—C37—H37C	109.5
H15A—C15—H15B	107.5	C8—N1—C9	124.4 (3)
O3—C21—O4	121.5 (3)	C8—N1—H1	118 (3)
O3—C21—C22	129.3 (4)	C9—N1—H1	114 (3)
O4—C21—C22	109.2 (3)	C29—N2—C28	122.6 (3)
C27—C22—C23	121.8 (3)	C29—N2—H2	120 (3)
C27—C22—C21	107.7 (3)	C28—N2—H2	117 (3)
C23—C22—C21	130.5 (3)	C35—N3—C36	128.6 (10)
C24—C23—C22	117.6 (4)	C35—N3—C37	117.6 (7)
C24—C23—H23	121.2	C36—N3—C37	113.3 (9)
C22—C23—H23	121.2	C1—O2—C8	110.5 (3)
C23—C24—C25	121.2 (4)	C21—O4—C28	110.6 (2)
O1—C1—C2—C7	−176.3 (4)	C23—C22—C27—C26	−1.5 (5)
O2—C1—C2—C7	2.2 (4)	C21—C22—C27—C26	179.1 (3)
O1—C1—C2—C3	4.9 (7)	C23—C22—C27—C28	177.7 (3)
O2—C1—C2—C3	−176.6 (4)	C21—C22—C27—C28	−1.7 (4)
C7—C2—C3—C4	−0.1 (6)	C25—C26—C27—C22	0.4 (5)
C1—C2—C3—C4	178.5 (4)	C25—C26—C27—C28	−178.7 (4)
C2—C3—C4—C5	−0.3 (7)	C22—C27—C28—N2	122.1 (3)
C3—C4—C5—C6	0.3 (7)	C26—C27—C28—N2	−58.8 (5)
C4—C5—C6—C7	0.3 (7)	C22—C27—C28—O4	1.6 (4)
C5—C6—C7—C2	−0.8 (6)	C26—C27—C28—O4	−179.3 (3)
C5—C6—C7—C8	−178.0 (4)	C34—C29—C30—C31	2.0 (5)
C3—C2—C7—C6	0.7 (6)	N2—C29—C30—C31	−175.8 (3)
C1—C2—C7—C6	−178.2 (3)	C29—C30—C31—C32	−1.4 (6)
C3—C2—C7—C8	178.4 (3)	C30—C31—C32—C33	−0.7 (6)
C1—C2—C7—C8	−0.5 (4)	C30—C31—C32—C15	−179.4 (4)
C6—C7—C8—N1	53.4 (5)	C12—C15—C32—C31	4.2 (6)
C2—C7—C8—N1	−124.0 (3)	C12—C15—C32—C33	−174.5 (4)
C6—C7—C8—O2	176.3 (4)	C31—C32—C33—C34	2.1 (6)
C2—C7—C8—O2	−1.2 (4)	C15—C32—C33—C34	−179.1 (4)
C14—C9—C10—C11	−0.1 (5)	C32—C33—C34—C29	−1.6 (6)
N1—C9—C10—C11	177.8 (3)	C30—C29—C34—C33	−0.5 (5)
C9—C10—C11—C12	0.5 (6)	N2—C29—C34—C33	177.3 (3)
C10—C11—C12—C13	−0.3 (5)	O2—C8—N1—C9	71.6 (4)
C10—C11—C12—C15	178.1 (3)	C7—C8—N1—C9	−171.9 (3)
C11—C12—C13—C14	−0.4 (5)	C14—C9—N1—C8	179.1 (3)
C15—C12—C13—C14	−178.8 (3)	C10—C9—N1—C8	1.2 (6)
C10—C9—C14—C13	−0.6 (5)	C30—C29—N2—C28	9.3 (5)
N1—C9—C14—C13	−178.6 (4)	C34—C29—N2—C28	−168.4 (3)
C12—C13—C14—C9	0.8 (6)	C27—C28—N2—C29	167.0 (3)
C11—C12—C15—C32	−102.8 (4)	O4—C28—N2—C29	−77.2 (4)
C13—C12—C15—C32	75.6 (5)	O5—C35—N3—C36	−5.6 (12)
O3—C21—C22—C27	−179.2 (4)	O5—C35—N3—C37	−177.2 (7)
O4—C21—C22—C27	1.1 (4)	O1—C1—O2—C8	175.6 (4)
O3—C21—C22—C23	1.5 (7)	C2—C1—O2—C8	−3.0 (4)
O4—C21—C22—C23	−178.2 (4)	N1—C8—O2—C1	125.2 (3)
C27—C22—C23—C24	1.3 (6)	C7—C8—O2—C1	2.6 (4)
C21—C22—C23—C24	−179.5 (4)	O3—C21—O4—C28	−179.8 (4)
C22—C23—C24—C25	0.0 (6)	C22—C21—O4—C28	−0.1 (4)
C23—C24—C25—C26	−1.2 (7)	N2—C28—O4—C21	−124.1 (3)
C24—C25—C26—C27	0.9 (6)	C27—C28—O4—C21	−0.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5	0.85 (2)	2.06 (2)	2.886 (5)	165 (4)
C34—H34···O5	0.93	2.81	3.505 (6)	133
N1—H1···O3^i	0.87 (2)	2.10 (2)	2.956 (4)	168 (4)
C5—H5···O2^ii	0.93	2.53	3.413 (6)	160
C8—H8···O1^iii	0.98	2.88	3.573 (5)	129
C25—H25···O4^iv	0.93	2.54	3.408 (4)	155
C36—H36b···O3^v	0.96	2.85	3.669 (13)	143
C37—H37c···O1^vi	0.96	2.60	3.208 (10)	121
C14—H14···Cg1^iv	0.93	3.00	3.735 (4)	137

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