9,10-Bis(3-hydroxy-3,3-di­phenyl­prop-1-ynyl)­anthracene N,N′-di­methyl­form­amide solvate

Sugadev, R.; Balasundaresan, D.; Chacko, K.K.; Ponnuswamy, M.N.; Sureshkumar, M.

doi:10.1107/S1600536801019845

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9,10-Bis(3-hydroxy-3,3-diphenylprop-1-ynyl)anthracene N,N′-dimethylformamide solvate

R. Sugadev, D. Balasundaresan, K. K. Chacko, M. N. Ponnuswamy and M. Sureshkumar

The X-ray crystal structure of the title compound, C₄₇H₃₇NO₃, has been determined. The zigzag packing of the molecules is stabilized by intermolecular O—H

O hydrogen bonds between the host and guest molecules, and intramolecular C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801019845/na6077sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801019845/na6077Isup2.hkl Contains datablock I

CCDC reference: 180768

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.058
wR factor = 0.176
Data-to-parameter ratio = 14.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



SYMMG_02
         From the CIF: _symmetry_equiv_pos_as_xyz
                                           x, y, z
                                           -x+1/2, y+1/2, -z+1/2
                                           -x, -y, -z
                                           x-1/2, -y-1/2, z-1/2
         These symops generate the Hall space group symbol   -p_2yn
         From the CIF: _symmetry_space_group_name_H-M     p_21/c
         From the xyz: _symmetry_space_group_name_H-M     p_1_21/n_1
          Alert A The _symmetry_equiv_pos_as_xyz values are inconsistent
          with the H-M symbol given


 Alert Level C:



ABSTM_02  Alert C The ratio of Tmax/Tmin expected RT(exp) is > 1.10
          Absorption corrections should be applied.
          Tmin and Tmax expected:      0.782     0.874
          RT(exp) =      1.118

DIFMX_01  Alert C The maximum difference density is > 0.1*ZMAX*0.75
          _refine_diff_density_max given =      0.606
          Test value =      0.600

DIFMX_02  Alert C The minimum difference density is > 0.1*ZMAX*0.75
          The relevant atom site should be identified.

SHFSU_01  Alert C The absolute value of parameter shift to su ratio > 0.05
          Absolute value of the parameter shift to su ratio given   0.062
          Additional refinement cycles may be required.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(9)   -   C(30)  =       1.44 Ang.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(10)  -   C(15)  =       1.43 Ang.

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     39
                   C13 -C10 -C15 -C16  -168.90  1.50   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     40
                   C11 -C10 -C15 -C16     9.80  1.60   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     41
                   C10 -C15 -C16 -C17    36.00  2.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     42
                   C15 -C16 -C17 -O1    -33.90  1.30   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     43
                   C15 -C16 -C17 -C18  -154.00  1.20   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     44
                   C15 -C16 -C17 -C24    82.50  1.20   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     73
                   C14 -C9  -C30 -C31  -174.00  3.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     74
                   C12 -C9  -C30 -C31     6.00  3.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     75
                   C9  -C30 -C31 -C32    50.00  5.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     76
                   C30 -C31 -C32 -O2    -43.00  3.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     77
                   C30 -C31 -C32 -C39  -164.00  3.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     78
                   C30 -C31 -C32 -C33    73.00  3.00   1.555   1.555   1.555   1.555


 1 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 18 Alert Level C = Please check

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SDP (Frenz ,1978); data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1995); software used to prepare material for publication: PARST (Nardelli, 1995).

9,10-Bis(3-hydroxy-3,3-diphenylprop-1-ynyl)anthracene N,N'dimethylformamide solvate top

Crystal data top

C₄₇H₃₇NO₃	F(000) = 1400
M_r = 663.78	D_x = 1.214 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 16.290 (3) Å	Cell parameters from 26 reflections
b = 11.837 (2) Å	θ = 5–20°
c = 19.426 (4) Å	µ = 0.59 mm⁻¹
β = 104.11 (3)°	T = 293 K
V = 3632.8 (12) Å³	Rectangular, yellow-brown
Z = 4	0.53 × 0.40 × 0.23 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	R_int = 0.015
Radiation source: fine-focus sealed tube	θ_max = 70.1°, θ_min = 3.2°
Graphite monochromator	h = 0→19
ω/2θ scans	k = 0→14
7151 measured reflections	l = −23→22
6910 independent reflections	3 standard reflections every 200 reflections
5927 reflections with I > 2σ(I)	intensity decay: <1.5%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.176	w = 1/[σ²(F_o²) + (0.0989P)² + 1.1549P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.062
6910 reflections	Δρ_max = 0.61 e Å⁻³
465 parameters	Δρ_min = −0.37 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0049 (4)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.97718 (8)	0.08492 (12)	0.33001 (8)	0.0520 (3)
H1	0.9680	0.1229	0.3626	0.078*
O2	0.68044 (9)	0.88981 (12)	0.06549 (7)	0.0512 (3)
H2	0.6482	0.8356	0.0587	0.077*
C1	0.75743 (12)	0.55950 (17)	0.17886 (10)	0.0477 (4)
H1A	0.7287	0.6214	0.1549	0.057*
C2	0.71994 (13)	0.4963 (2)	0.22060 (11)	0.0560 (5)
H2A	0.6661	0.5153	0.2251	0.067*
C3	0.76179 (14)	0.40185 (19)	0.25730 (11)	0.0556 (5)
H3	0.7351	0.3583	0.2852	0.067*
C4	0.84071 (13)	0.37428 (16)	0.25212 (10)	0.0480 (4)
H4	0.8680	0.3126	0.2774	0.058*
C5	1.08582 (13)	0.44449 (18)	0.14725 (12)	0.0547 (5)
H5	1.1153	0.3840	0.1722	0.066*
C6	1.12163 (15)	0.5052 (2)	0.10320 (14)	0.0676 (6)
H6	1.1756	0.4866	0.0988	0.081*
C7	1.07803 (16)	0.5962 (2)	0.06408 (14)	0.0658 (6)
H7	1.1030	0.6366	0.0335	0.079*
C8	0.99976 (13)	0.62543 (16)	0.07066 (11)	0.0518 (5)
H8	0.9717	0.6857	0.0444	0.062*
C9	0.87928 (11)	0.59571 (13)	0.12585 (8)	0.0384 (4)
C10	0.96502 (11)	0.40958 (13)	0.20151 (9)	0.0382 (4)
C11	0.88296 (11)	0.43800 (14)	0.20864 (8)	0.0377 (4)
C12	0.83990 (11)	0.53323 (14)	0.17080 (8)	0.0381 (4)
C13	1.00378 (11)	0.47153 (14)	0.15610 (9)	0.0405 (4)
C14	0.95984 (11)	0.56541 (14)	0.11709 (9)	0.0402 (4)
C15	1.00660 (11)	0.31449 (14)	0.24080 (9)	0.0420 (4)
C16	1.03343 (11)	0.23320 (14)	0.27499 (9)	0.0431 (4)
C17	1.05286 (10)	0.12398 (14)	0.31271 (9)	0.0392 (4)
C18	1.12256 (10)	0.13315 (14)	0.38101 (9)	0.0372 (4)
C19	1.14088 (12)	0.03777 (16)	0.42346 (10)	0.0490 (4)
H19	1.1139	−0.0301	0.4080	0.059*
C20	1.19885 (14)	0.04251 (19)	0.48847 (11)	0.0582 (5)
H20	1.2101	−0.0217	0.5168	0.070*
C21	1.23993 (14)	0.14241 (19)	0.51134 (11)	0.0581 (5)
H21	1.2781	0.1462	0.5555	0.070*
C22	1.22426 (14)	0.23600 (18)	0.46880 (12)	0.0592 (5)
H22	1.2533	0.3028	0.4835	0.071*
C23	1.16511 (12)	0.23172 (15)	0.40376 (11)	0.0500 (5)
H23	1.1543	0.2960	0.3755	0.060*
C24	1.07643 (12)	0.03877 (14)	0.26123 (9)	0.0425 (4)
C25	1.15366 (16)	0.0466 (2)	0.24425 (12)	0.0627 (6)
H25	1.1917	0.1029	0.2648	0.075*
C26	1.1751 (2)	−0.0286 (2)	0.19675 (15)	0.0804 (8)
H26	1.2273	−0.0228	0.1856	0.097*
C27	1.1194 (2)	−0.1117 (2)	0.16622 (13)	0.0771 (8)
H27	1.1340	−0.1628	0.1349	0.093*
C28	1.04244 (19)	−0.1188 (2)	0.18212 (13)	0.0711 (7)
H28	1.0043	−0.1744	0.1607	0.085*
C29	1.02027 (14)	−0.04463 (17)	0.22965 (12)	0.0569 (5)
H29	0.9678	−0.0508	0.2403	0.068*
C30	0.83531 (11)	0.69189 (14)	0.08903 (9)	0.0427 (4)
C31	0.79588 (12)	0.77042 (14)	0.06061 (9)	0.0432 (4)
C32	0.74636 (11)	0.87155 (14)	0.03015 (9)	0.0387 (4)
C33	0.80634 (11)	0.97344 (14)	0.04665 (9)	0.0397 (4)
C34	0.86492 (12)	0.99401 (16)	0.00708 (11)	0.0495 (4)
H34	0.8663	0.9480	−0.0314	0.059*
C35	0.92173 (14)	1.08321 (19)	0.02480 (13)	0.0599 (5)
H35	0.9606	1.0971	−0.0022	0.072*
C36	0.92067 (15)	1.15095 (18)	0.08201 (12)	0.0627 (6)
H36	0.9594	1.2097	0.0942	0.075*
C37	0.86250 (16)	1.13162 (18)	0.12091 (11)	0.0622 (6)
H37	0.8615	1.1779	0.1594	0.075*
C38	0.80485 (14)	1.04343 (16)	0.10340 (10)	0.0514 (5)
H38	0.7652	1.0314	0.1299	0.062*
C39	0.70815 (11)	0.85851 (14)	−0.04973 (9)	0.0416 (4)
C40	0.65493 (14)	0.94308 (18)	−0.08403 (11)	0.0568 (5)
H40	0.6452	1.0063	−0.0588	0.068*
C41	0.61631 (17)	0.9343 (2)	−0.15531 (13)	0.0729 (7)
H41	0.5804	0.9915	−0.1777	0.087*
C42	0.6303 (2)	0.8423 (2)	−0.19341 (12)	0.0813 (8)
H42	0.6037	0.8363	−0.2414	0.098*
C43	0.6839 (2)	0.7592 (2)	−0.16021 (13)	0.0901 (10)
H43	0.6945	0.6968	−0.1859	0.108*
C44	0.72250 (18)	0.76755 (18)	−0.08840 (12)	0.0677 (7)
H44	0.7586	0.7104	−0.0663	0.081*
O1A	0.55518 (14)	0.7170 (2)	0.05586 (13)	0.0931 (6)
N1A	0.46411 (15)	0.7528 (2)	−0.05206 (13)	0.0777 (6)
C1A	0.5137 (3)	0.6843 (3)	−0.0021 (3)	0.1059 (12)
H1A1	0.5162	0.6079	−0.0127	0.127*
C2A	0.4581 (3)	0.8667 (3)	−0.0378 (3)	0.1328 (16)
H2A1	0.4744	0.8787	0.0126	0.199*
H2A2	0.4008	0.8915	−0.0561	0.199*
H2A3	0.4950	0.9088	−0.0600	0.199*
C3A	0.4212 (4)	0.7036 (6)	−0.1176 (3)	0.182 (3)
H3A1	0.4363	0.6253	−0.1181	0.273*
H3A2	0.4371	0.7422	−0.1559	0.273*
H3A3	0.3612	0.7102	−0.1232	0.273*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0401 (7)	0.0508 (8)	0.0624 (9)	−0.0071 (6)	0.0070 (6)	−0.0022 (6)
O2	0.0525 (8)	0.0481 (7)	0.0536 (8)	0.0019 (6)	0.0138 (6)	−0.0006 (6)
C1	0.0500 (10)	0.0471 (10)	0.0424 (9)	0.0156 (8)	0.0042 (8)	0.0052 (8)
C2	0.0496 (10)	0.0680 (13)	0.0504 (11)	0.0128 (9)	0.0119 (9)	0.0054 (9)
C3	0.0604 (12)	0.0609 (12)	0.0471 (10)	0.0048 (10)	0.0161 (9)	0.0108 (9)
C4	0.0569 (11)	0.0437 (10)	0.0406 (9)	0.0087 (8)	0.0066 (8)	0.0089 (7)
C5	0.0475 (10)	0.0472 (11)	0.0664 (13)	0.0080 (8)	0.0082 (9)	0.0000 (9)
C6	0.0527 (12)	0.0658 (14)	0.0883 (17)	0.0020 (10)	0.0251 (12)	0.0006 (12)
C7	0.0693 (14)	0.0571 (13)	0.0782 (15)	−0.0053 (11)	0.0317 (12)	0.0052 (11)
C8	0.0604 (12)	0.0391 (10)	0.0547 (11)	−0.0025 (8)	0.0117 (9)	0.0037 (8)
C9	0.0467 (9)	0.0276 (8)	0.0343 (8)	0.0028 (7)	−0.0028 (7)	0.0006 (6)
C10	0.0420 (9)	0.0292 (8)	0.0360 (8)	0.0046 (6)	−0.0049 (7)	−0.0011 (6)
C11	0.0452 (9)	0.0316 (8)	0.0308 (8)	0.0049 (7)	−0.0018 (6)	0.0001 (6)
C12	0.0437 (9)	0.0328 (8)	0.0319 (8)	0.0063 (7)	−0.0020 (7)	−0.0006 (6)
C13	0.0422 (9)	0.0317 (8)	0.0420 (9)	0.0012 (7)	−0.0003 (7)	−0.0040 (7)
C14	0.0472 (9)	0.0304 (8)	0.0382 (8)	−0.0009 (7)	0.0010 (7)	−0.0025 (6)
C15	0.0436 (9)	0.0334 (9)	0.0411 (9)	0.0031 (7)	−0.0048 (7)	−0.0007 (7)
C16	0.0420 (9)	0.0338 (9)	0.0451 (9)	0.0042 (7)	−0.0056 (7)	0.0001 (7)
C17	0.0373 (8)	0.0307 (8)	0.0444 (9)	0.0002 (6)	0.0000 (7)	0.0031 (7)
C18	0.0356 (8)	0.0333 (8)	0.0399 (8)	0.0042 (6)	0.0036 (7)	0.0023 (6)
C19	0.0542 (11)	0.0366 (9)	0.0502 (10)	0.0002 (8)	0.0012 (8)	0.0081 (8)
C20	0.0650 (12)	0.0545 (12)	0.0480 (11)	0.0078 (10)	−0.0002 (9)	0.0156 (9)
C21	0.0561 (11)	0.0643 (13)	0.0442 (10)	0.0073 (10)	−0.0066 (9)	−0.0007 (9)
C22	0.0576 (12)	0.0490 (11)	0.0587 (12)	−0.0038 (9)	−0.0094 (9)	−0.0057 (9)
C23	0.0515 (10)	0.0346 (9)	0.0545 (11)	−0.0008 (8)	−0.0051 (8)	0.0036 (8)
C24	0.0521 (10)	0.0310 (8)	0.0388 (9)	0.0038 (7)	0.0001 (7)	0.0046 (7)
C25	0.0744 (14)	0.0548 (12)	0.0634 (13)	−0.0096 (11)	0.0256 (11)	−0.0079 (10)
C26	0.100 (2)	0.0784 (18)	0.0746 (16)	0.0000 (15)	0.0446 (15)	−0.0061 (14)
C27	0.125 (2)	0.0579 (14)	0.0499 (12)	0.0108 (15)	0.0235 (14)	−0.0072 (10)
C28	0.0997 (19)	0.0473 (12)	0.0547 (13)	0.0003 (12)	−0.0036 (12)	−0.0116 (10)
C29	0.0605 (12)	0.0435 (10)	0.0569 (12)	−0.0004 (9)	−0.0043 (9)	−0.0046 (9)
C30	0.0502 (10)	0.0320 (8)	0.0394 (9)	0.0020 (7)	−0.0018 (7)	0.0020 (7)
C31	0.0508 (10)	0.0326 (9)	0.0396 (9)	0.0003 (7)	−0.0021 (7)	0.0026 (7)
C32	0.0439 (9)	0.0308 (8)	0.0377 (8)	0.0043 (7)	0.0030 (7)	0.0038 (6)
C33	0.0465 (9)	0.0294 (8)	0.0361 (8)	0.0048 (7)	−0.0040 (7)	0.0045 (6)
C34	0.0503 (10)	0.0409 (10)	0.0550 (11)	0.0003 (8)	0.0088 (8)	−0.0043 (8)
C35	0.0515 (11)	0.0524 (12)	0.0725 (14)	−0.0060 (9)	0.0087 (10)	0.0029 (10)
C36	0.0674 (13)	0.0430 (11)	0.0631 (13)	−0.0116 (10)	−0.0124 (11)	0.0005 (9)
C37	0.0881 (16)	0.0440 (11)	0.0442 (10)	−0.0087 (10)	−0.0036 (10)	−0.0074 (8)
C38	0.0710 (13)	0.0400 (10)	0.0384 (9)	−0.0020 (9)	0.0041 (9)	−0.0006 (7)
C39	0.0470 (9)	0.0314 (8)	0.0400 (9)	−0.0016 (7)	−0.0019 (7)	0.0031 (7)
C40	0.0668 (13)	0.0449 (10)	0.0492 (11)	0.0134 (9)	−0.0043 (9)	0.0055 (8)
C41	0.0819 (16)	0.0614 (14)	0.0569 (13)	0.0063 (12)	−0.0190 (11)	0.0135 (11)
C42	0.116 (2)	0.0609 (14)	0.0457 (12)	−0.0142 (14)	−0.0224 (13)	0.0031 (10)
C43	0.150 (3)	0.0514 (13)	0.0510 (13)	0.0050 (15)	−0.0098 (15)	−0.0140 (10)
C44	0.1019 (18)	0.0384 (10)	0.0502 (11)	0.0145 (11)	−0.0056 (11)	−0.0044 (9)
O1A	0.0860 (13)	0.0960 (15)	0.0995 (15)	−0.0252 (12)	0.0269 (11)	0.0015 (12)
N1A	0.0759 (14)	0.0705 (14)	0.0899 (15)	−0.0071 (11)	0.0267 (12)	−0.0147 (12)
C1A	0.115 (3)	0.0684 (19)	0.153 (4)	−0.0100 (19)	0.068 (3)	−0.013 (2)
C2A	0.129 (3)	0.082 (2)	0.198 (5)	0.004 (2)	0.061 (3)	−0.018 (3)
C3A	0.207 (6)	0.223 (6)	0.124 (4)	−0.067 (5)	0.053 (4)	−0.081 (4)

Geometric parameters (Å, º) top

O1—C17	1.431 (2)	C25—C26	1.387 (3)
O1—H1	0.8200	C25—H25	0.9300
O2—C32	1.425 (2)	C26—C27	1.370 (4)
O2—H2	0.8200	C26—H26	0.9300
C1—C2	1.353 (3)	C27—C28	1.365 (4)
C1—C12	1.424 (3)	C27—H27	0.9300
C1—H1A	0.9300	C28—C29	1.384 (3)
C2—C3	1.409 (3)	C28—H28	0.9300
C2—H2A	0.9300	C29—H29	0.9300
C3—C4	1.354 (3)	C30—C31	1.187 (2)
C3—H3	0.9300	C31—C32	1.484 (2)
C4—C11	1.428 (3)	C32—C39	1.532 (2)
C4—H4	0.9300	C32—C33	1.536 (2)
C5—C6	1.354 (3)	C33—C38	1.384 (3)
C5—C13	1.425 (3)	C33—C34	1.385 (3)
C5—H5	0.9300	C34—C35	1.391 (3)
C6—C7	1.407 (3)	C34—H34	0.9300
C6—H6	0.9300	C35—C36	1.374 (3)
C7—C8	1.357 (3)	C35—H35	0.9300
C7—H7	0.9300	C36—C37	1.368 (4)
C8—C14	1.424 (3)	C36—H36	0.9300
C8—H8	0.9300	C37—C38	1.390 (3)
C9—C14	1.410 (3)	C37—H37	0.9300
C9—C12	1.412 (2)	C38—H38	0.9300
C9—C30	1.439 (2)	C39—C44	1.365 (3)
C10—C13	1.409 (3)	C39—C40	1.384 (2)
C10—C11	1.418 (2)	C40—C41	1.378 (3)
C10—C15	1.434 (2)	C40—H40	0.9300
C11—C12	1.432 (2)	C41—C42	1.366 (4)
C13—C14	1.434 (2)	C41—H41	0.9300
C15—C16	1.190 (2)	C42—C43	1.368 (4)
C16—C17	1.482 (2)	C42—H42	0.9300
C17—C18	1.525 (2)	C43—C44	1.387 (3)
C17—C24	1.534 (3)	C43—H43	0.9300
C18—C23	1.374 (2)	C44—H44	0.9300
C18—C19	1.387 (2)	O1A—C1A	1.225 (5)
C19—C20	1.381 (3)	N1A—C1A	1.368 (5)
C19—H19	0.9300	N1A—C2A	1.385 (4)
C20—C21	1.378 (3)	N1A—C3A	1.419 (5)
C20—H20	0.9300	C1A—H1A1	0.9300
C21—C22	1.368 (3)	C2A—H2A1	0.9600
C21—H21	0.9300	C2A—H2A2	0.9600
C22—C23	1.391 (3)	C2A—H2A3	0.9600
C22—H22	0.9300	C3A—H3A1	0.9600
C23—H23	0.9300	C3A—H3A2	0.9600
C24—C25	1.379 (3)	C3A—H3A3	0.9600
C24—C29	1.384 (3)

C17—O1—H1	109.5	C26—C25—H25	119.7
C32—O2—H2	109.5	C27—C26—C25	120.1 (3)
C2—C1—C12	121.37 (17)	C27—C26—H26	120.0
C2—C1—H1A	119.3	C25—C26—H26	120.0
C12—C1—H1A	119.3	C28—C27—C26	119.6 (2)
C1—C2—C3	120.56 (19)	C28—C27—H27	120.2
C1—C2—H2A	119.7	C26—C27—H27	120.2
C3—C2—H2A	119.7	C27—C28—C29	121.0 (2)
C4—C3—C2	120.30 (19)	C27—C28—H28	119.5
C4—C3—H3	119.8	C29—C28—H28	119.5
C2—C3—H3	119.8	C24—C29—C28	119.8 (2)
C3—C4—C11	121.34 (17)	C24—C29—H29	120.1
C3—C4—H4	119.3	C28—C29—H29	120.1
C11—C4—H4	119.3	C31—C30—C9	176.5 (2)
C6—C5—C13	121.2 (2)	C30—C31—C32	175.93 (19)
C6—C5—H5	119.4	O2—C32—C31	109.31 (14)
C13—C5—H5	119.4	O2—C32—C39	109.59 (14)
C5—C6—C7	120.6 (2)	C31—C32—C39	111.70 (14)
C5—C6—H6	119.7	O2—C32—C33	107.22 (14)
C7—C6—H6	119.7	C31—C32—C33	107.10 (14)
C8—C7—C6	120.4 (2)	C39—C32—C33	111.78 (14)
C8—C7—H7	119.8	C38—C33—C34	119.02 (17)
C6—C7—H7	119.8	C38—C33—C32	120.16 (17)
C7—C8—C14	121.15 (19)	C34—C33—C32	120.77 (16)
C7—C8—H8	119.4	C33—C34—C35	120.20 (19)
C14—C8—H8	119.4	C33—C34—H34	119.9
C14—C9—C12	121.19 (15)	C35—C34—H34	119.9
C14—C9—C30	120.42 (16)	C36—C35—C34	120.3 (2)
C12—C9—C30	118.39 (16)	C36—C35—H35	119.9
C13—C10—C11	120.98 (15)	C34—C35—H35	119.9
C13—C10—C15	121.07 (16)	C37—C36—C35	119.8 (2)
C11—C10—C15	117.94 (16)	C37—C36—H36	120.1
C10—C11—C4	122.31 (15)	C35—C36—H36	120.1
C10—C11—C12	119.47 (16)	C36—C37—C38	120.6 (2)
C4—C11—C12	118.22 (16)	C36—C37—H37	119.7
C9—C12—C1	122.45 (15)	C38—C37—H37	119.7
C9—C12—C11	119.34 (15)	C33—C38—C37	120.2 (2)
C1—C12—C11	118.19 (16)	C33—C38—H38	119.9
C10—C13—C5	122.36 (16)	C37—C38—H38	119.9
C10—C13—C14	119.46 (16)	C44—C39—C40	118.46 (18)
C5—C13—C14	118.18 (17)	C44—C39—C32	123.70 (16)
C9—C14—C8	122.13 (16)	C40—C39—C32	117.83 (16)
C9—C14—C13	119.50 (16)	C41—C40—C39	120.5 (2)
C8—C14—C13	118.37 (17)	C41—C40—H40	119.7
C16—C15—C10	173.3 (2)	C39—C40—H40	119.7
C15—C16—C17	170.59 (18)	C42—C41—C40	120.6 (2)
O1—C17—C16	107.79 (14)	C42—C41—H41	119.7
O1—C17—C18	108.66 (14)	C40—C41—H41	119.7
C16—C17—C18	113.08 (14)	C41—C42—C43	119.3 (2)
O1—C17—C24	107.91 (14)	C41—C42—H42	120.4
C16—C17—C24	107.98 (14)	C43—C42—H42	120.4
C18—C17—C24	111.24 (13)	C42—C43—C44	120.2 (2)
C23—C18—C19	118.77 (16)	C42—C43—H43	119.9
C23—C18—C17	123.39 (15)	C44—C43—H43	119.9
C19—C18—C17	117.77 (15)	C39—C44—C43	120.9 (2)
C20—C19—C18	120.71 (18)	C39—C44—H44	119.6
C20—C19—H19	119.6	C43—C44—H44	119.6
C18—C19—H19	119.6	C1A—N1A—C2A	119.5 (3)
C21—C20—C19	119.97 (18)	C1A—N1A—C3A	118.1 (4)
C21—C20—H20	120.0	C2A—N1A—C3A	122.4 (4)
C19—C20—H20	120.0	O1A—C1A—N1A	124.2 (3)
C22—C21—C20	119.71 (18)	O1A—C1A—H1A1	117.9
C22—C21—H21	120.1	N1A—C1A—H1A1	117.9
C20—C21—H21	120.1	N1A—C2A—H2A1	109.5
C21—C22—C23	120.34 (19)	N1A—C2A—H2A2	109.5
C21—C22—H22	119.8	H2A1—C2A—H2A2	109.5
C23—C22—H22	119.8	N1A—C2A—H2A3	109.5
C18—C23—C22	120.44 (18)	H2A1—C2A—H2A3	109.5
C18—C23—H23	119.8	H2A2—C2A—H2A3	109.5
C22—C23—H23	119.8	N1A—C3A—H3A1	109.5
C25—C24—C29	119.02 (19)	N1A—C3A—H3A2	109.5
C25—C24—C17	119.97 (17)	H3A1—C3A—H3A2	109.5
C29—C24—C17	120.98 (18)	N1A—C3A—H3A3	109.5
C24—C25—C26	120.5 (2)	H3A1—C3A—H3A3	109.5
C24—C25—H25	119.7	H3A2—C3A—H3A3	109.5

C12—C1—C2—C3	−0.2 (3)	C20—C21—C22—C23	2.1 (4)
C1—C2—C3—C4	1.1 (3)	C19—C18—C23—C22	−1.2 (3)
C2—C3—C4—C11	−1.2 (3)	C17—C18—C23—C22	175.90 (19)
C13—C5—C6—C7	−0.8 (4)	C21—C22—C23—C18	−0.9 (3)
C5—C6—C7—C8	0.9 (4)	O1—C17—C24—C25	−170.24 (17)
C6—C7—C8—C14	0.1 (3)	C16—C17—C24—C25	73.5 (2)
C13—C10—C11—C4	177.57 (16)	C18—C17—C24—C25	−51.1 (2)
C15—C10—C11—C4	−1.2 (2)	O1—C17—C24—C29	11.6 (2)
C13—C10—C11—C12	−1.9 (2)	C16—C17—C24—C29	−104.62 (19)
C15—C10—C11—C12	179.31 (14)	C18—C17—C24—C29	130.74 (17)
C3—C4—C11—C10	−178.95 (18)	C29—C24—C25—C26	−0.7 (3)
C3—C4—C11—C12	0.6 (3)	C17—C24—C25—C26	−178.8 (2)
C14—C9—C12—C1	−177.84 (16)	C24—C25—C26—C27	0.0 (4)
C30—C9—C12—C1	2.3 (2)	C25—C26—C27—C28	0.9 (4)
C14—C9—C12—C11	0.6 (2)	C26—C27—C28—C29	−1.2 (4)
C30—C9—C12—C11	−179.24 (14)	C25—C24—C29—C28	0.4 (3)
C2—C1—C12—C9	177.96 (18)	C17—C24—C29—C28	178.51 (18)
C2—C1—C12—C11	−0.5 (3)	C27—C28—C29—C24	0.5 (3)
C10—C11—C12—C9	1.3 (2)	C14—C9—C30—C31	−174 (3)
C4—C11—C12—C9	−178.19 (15)	C12—C9—C30—C31	6 (3)
C10—C11—C12—C1	179.82 (15)	C9—C30—C31—C32	50 (5)
C4—C11—C12—C1	0.3 (2)	C30—C31—C32—O2	−43 (3)
C11—C10—C13—C5	−179.40 (16)	C30—C31—C32—C39	−164 (3)
C15—C10—C13—C5	−0.7 (3)	C30—C31—C32—C33	73 (3)
C11—C10—C13—C14	0.6 (2)	O2—C32—C33—C38	18.1 (2)
C15—C10—C13—C14	179.34 (15)	C31—C32—C33—C38	−99.12 (19)
C6—C5—C13—C10	179.9 (2)	C39—C32—C33—C38	138.23 (17)
C6—C5—C13—C14	−0.1 (3)	O2—C32—C33—C34	−164.61 (15)
C12—C9—C14—C8	178.35 (16)	C31—C32—C33—C34	78.17 (19)
C30—C9—C14—C8	−1.8 (2)	C39—C32—C33—C34	−44.5 (2)
C12—C9—C14—C13	−1.9 (2)	C38—C33—C34—C35	0.6 (3)
C30—C9—C14—C13	177.93 (15)	C32—C33—C34—C35	−176.75 (17)
C7—C8—C14—C9	178.69 (19)	C33—C34—C35—C36	0.6 (3)
C7—C8—C14—C13	−1.1 (3)	C34—C35—C36—C37	−1.1 (3)
C10—C13—C14—C9	1.3 (2)	C35—C36—C37—C38	0.5 (3)
C5—C13—C14—C9	−178.69 (16)	C34—C33—C38—C37	−1.2 (3)
C10—C13—C14—C8	−178.95 (16)	C32—C33—C38—C37	176.17 (17)
C5—C13—C14—C8	1.1 (2)	C36—C37—C38—C33	0.6 (3)
C13—C10—C15—C16	−168.9 (15)	O2—C32—C39—C44	−124.9 (2)
C11—C10—C15—C16	9.8 (16)	C31—C32—C39—C44	−3.7 (3)
C10—C15—C16—C17	36 (2)	C33—C32—C39—C44	116.3 (2)
C15—C16—C17—O1	−33.9 (13)	O2—C32—C39—C40	53.9 (2)
C15—C16—C17—C18	−154.0 (12)	C31—C32—C39—C40	175.15 (18)
C15—C16—C17—C24	82.5 (12)	C33—C32—C39—C40	−64.9 (2)
O1—C17—C18—C23	−121.96 (18)	C44—C39—C40—C41	1.1 (4)
C16—C17—C18—C23	−2.3 (3)	C32—C39—C40—C41	−177.7 (2)
C24—C17—C18—C23	119.39 (19)	C39—C40—C41—C42	−0.4 (4)
O1—C17—C18—C19	55.2 (2)	C40—C41—C42—C43	−0.7 (5)
C16—C17—C18—C19	174.81 (17)	C41—C42—C43—C44	1.0 (5)
C24—C17—C18—C19	−63.5 (2)	C40—C39—C44—C43	−0.8 (4)
C23—C18—C19—C20	2.1 (3)	C32—C39—C44—C43	178.0 (2)
C17—C18—C19—C20	−175.22 (18)	C42—C43—C44—C39	−0.2 (5)
C18—C19—C20—C21	−0.8 (3)	C2A—N1A—C1A—O1A	−0.7 (5)
C19—C20—C21—C22	−1.3 (4)	C3A—N1A—C1A—O1A	178.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1A	0.82	2.06	2.863 (3)	168
C29—H29···O1	0.93	2.35	2.704 (3)	102
C38—H38···O2	0.93	2.33	2.689 (2)	102
C2A—H2A1···O1A	0.96	2.36	2.747 (5)	104
O1—H1···O1Aⁱ	0.82	2.04	2.865 (3)	180
C2—H2A···O1ⁱⁱ	0.93	2.46	3.292 (2)	149

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

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