Crystal structure of bis-p-anizidinegossypol with an unknown solvate

In the solid-state, bis-p-anizidinegossypol exists in the enamine or quinoid form. The naphthyl moieties are close to perpendicular [dihedral angle = 72.08 (5)°]. In the crystal, mol­ecules are linked by O—H...O hydrogen bonds, generating layers which surround channels occupied by disordered guest mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.051
• wR factor = 0.124
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         30 %
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......      0.956 Note
PLAT410_ALERT_2_B Short Intra H...H Contact  H4A    ..  H23     ..       1.84 Ang.

Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            broun
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.649
PLAT220_ALERT_2_C Large Non-Solvent  C     Ueq(max)/Ueq(min) Range        3.6 Ratio
PLAT222_ALERT_3_C Large Non-Solvent  H     Uiso(max)/Uiso(min) ...        4.1 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     --  C3      ..        5.3 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     --  C10     ..        6.7 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C14    --  C20     ..        5.3 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C18    --  C27     ..        5.3 su
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....        C39 Check
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....        C40 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        C23 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        C31 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        C38 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        C41 Check
PLAT334_ALERT_2_C Small Average Benzene  C-C Dist. C38    -C43           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0046 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H14    ..  H28     ..       1.91 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     39.239 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      7.116 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.919 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         90 Report

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C5     -C10           1.43 Ang.
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C15    -C20           1.42 Ang.
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C26 Check
PLAT606_ALERT_4_G VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info
PLAT869_ALERT_4_G ALERTS Related to the use of SQUEEZE Suppressed           ! Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          2 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        294 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   3 ALERT level B = A potentially serious problem, consider carefully
  22 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  11 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1,1',6,6'-Tetrahydroxy-5,5'-diisopropyl-8,8'-bis{[(4-methoxyphenyl)iminiumyl]methyl}-3,3'-dimethyl-2,2'-binaphthalene-7,7'-diolate

Crystal data

C44H44N2O8	Z = 2
Mr = 728.81	F(000) = 772
Triclinic, P1	Dx = 0.983 Mg m^−3
a = 11.6622 (9) Å	Cu Kα radiation, λ = 1.54184 Å
b = 14.0738 (11) Å	Cell parameters from 2564 reflections
c = 15.6906 (10) Å	θ = 3.9–70.6°
α = 82.472 (6)°	µ = 0.55 mm^−1
β = 84.831 (6)°	T = 293 K
γ = 75.009 (7)°	Prism, broun
V = 2462.0 (3) Å^3	0.40 × 0.32 × 0.27 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer	9019 independent reflections
Radiation source: fine-focus sealed tube	2706 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 10.2576 pixels mm^-1	θmax = 70.6°, θmin = 3.9°
ω scans	h = −14→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −16→16
Tmin = 0.811, Tmax = 0.862	l = −18→16
18952 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 0.65	w = 1/[σ^2(Fo^2) + (0.0542P)^2] where P = (Fo^2 + 2Fc^2)/3
9019 reflections	(Δ/σ)max < 0.001
519 parameters	Δρmax = 0.13 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

Experimental. Absorption correction: CrysAlisPro, Oxford Diffraction (2009), Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
O1	−0.06997 (18)	0.40724 (17)	0.33397 (13)	0.0668 (6)
O2	−0.6101 (2)	0.2359 (2)	0.58343 (19)	0.1250 (10)
O3	−0.23580 (18)	0.62089 (16)	0.58330 (12)	0.0774 (6)
O4	−0.1425 (2)	0.7699 (2)	0.55783 (17)	0.0923 (8)
O5	0.27695 (17)	0.35008 (18)	0.24986 (14)	0.0741 (7)
O6	0.97592 (18)	0.21416 (17)	0.27160 (14)	0.0886 (7)
O7	0.46897 (19)	0.06734 (18)	0.07019 (15)	0.1002 (9)
O8	0.3149 (2)	0.06336 (18)	−0.03842 (14)	0.0887 (8)
N1	−0.2902 (2)	0.4750 (2)	0.53257 (17)	0.0736 (8)
N2	0.5550 (2)	0.1627 (2)	0.16491 (18)	0.0824 (9)
C1	−0.0203 (2)	0.4872 (2)	0.32283 (17)	0.0543 (7)
C2	0.0593 (2)	0.4959 (2)	0.25382 (17)	0.0546 (8)
C3	0.1135 (3)	0.5752 (2)	0.24359 (18)	0.0657 (9)
C4	0.0827 (3)	0.6422 (2)	0.30335 (19)	0.0677 (9)
H4A	0.1188	0.6946	0.2968	0.081*
C5	−0.0267 (3)	0.7112 (2)	0.43314 (19)	0.0680 (9)
C6	−0.1066 (3)	0.7018 (2)	0.4998 (2)	0.0681 (9)
C7	−0.1641 (3)	0.6211 (2)	0.51583 (18)	0.0627 (9)
C8	−0.1427 (2)	0.5498 (2)	0.45576 (17)	0.0570 (8)
C9	−0.0561 (2)	0.5568 (2)	0.38381 (17)	0.0537 (8)
C10	0.0002 (2)	0.6367 (2)	0.37361 (18)	0.0600 (8)
C11	0.1982 (2)	0.3535 (2)	0.18905 (16)	0.0563 (8)
C12	0.0890 (2)	0.4206 (2)	0.19037 (17)	0.0587 (8)
C13	0.0074 (2)	0.4204 (2)	0.12890 (17)	0.0615 (8)
C14	0.0405 (3)	0.3496 (2)	0.07254 (17)	0.0688 (9)
H14	−0.0149	0.3470	0.0344	0.083*
C15	0.1802 (2)	0.2079 (2)	0.00811 (18)	0.0623 (8)
C16	0.2827 (3)	0.1384 (2)	0.01332 (18)	0.0677 (9)
C17	0.3742 (3)	0.1370 (3)	0.07291 (19)	0.0730 (10)
C18	0.3505 (2)	0.2143 (2)	0.12572 (17)	0.0601 (8)
C19	0.2357 (2)	0.2845 (2)	0.12808 (17)	0.0571 (8)
C20	0.1511 (2)	0.2814 (2)	0.06846 (17)	0.0591 (8)
C21	0.1981 (3)	0.5900 (2)	0.16700 (19)	0.0862 (11)
H21A	0.2164	0.6529	0.1662	0.129*
H21B	0.1616	0.5886	0.1149	0.129*
H21C	0.2700	0.5381	0.1713	0.129*
C22	−0.2114 (3)	0.4812 (2)	0.46653 (19)	0.0642 (8)
H22	−0.2017	0.4374	0.4254	0.077*
C23	0.0276 (4)	0.7993 (3)	0.4206 (2)	0.0993 (13)
H23	0.0914	0.7849	0.3755	0.119*
C24	0.0868 (4)	0.8144 (3)	0.4976 (3)	0.1269 (15)
H24A	0.1543	0.8405	0.4785	0.190*
H24B	0.1126	0.7522	0.5323	0.190*
H24C	0.0313	0.8601	0.5312	0.190*
C25	−0.0552 (5)	0.8930 (4)	0.3869 (3)	0.192 (3)
H25A	−0.0664	0.8912	0.3274	0.288*
H25B	−0.0226	0.9478	0.3925	0.288*
H25C	−0.1304	0.9008	0.4192	0.288*
C26	−0.1129 (3)	0.4922 (2)	0.12655 (19)	0.0819 (10)
H26A	−0.1553	0.4803	0.0810	0.123*
H26B	−0.1035	0.5586	0.1166	0.123*
H26C	−0.1567	0.4836	0.1806	0.123*
C27	0.4492 (3)	0.2255 (2)	0.16703 (18)	0.0742 (10)
H27	0.4385	0.2801	0.1972	0.089*
C28	0.0952 (3)	0.2073 (3)	−0.0607 (2)	0.0935 (13)
H28	0.0313	0.2681	−0.0592	0.112*
C29	0.1528 (3)	0.2089 (3)	−0.1511 (2)	0.1217 (16)
H29A	0.1918	0.2619	−0.1618	0.183*
H29B	0.0930	0.2187	−0.1919	0.183*
H29C	0.2101	0.1471	−0.1571	0.183*
C30	0.0377 (4)	0.1211 (4)	−0.0378 (3)	0.1432 (19)
H30A	−0.0126	0.1310	0.0138	0.215*
H30B	0.0985	0.0606	−0.0287	0.215*
H30C	−0.0089	0.1174	−0.0841	0.215*
C31	−0.3701 (3)	0.4116 (3)	0.5449 (2)	0.0736 (9)
C32	−0.4309 (3)	0.4051 (3)	0.6236 (2)	0.1032 (13)
H32	−0.4178	0.4399	0.6668	0.124*
C33	−0.5130 (3)	0.3461 (3)	0.6395 (3)	0.1062 (13)
H33	−0.5537	0.3408	0.6930	0.127*
C34	−0.5315 (3)	0.2971 (3)	0.5753 (3)	0.0971 (12)
C35	−0.4745 (3)	0.3059 (3)	0.4958 (3)	0.1026 (12)
H35	−0.4903	0.2730	0.4523	0.123*
C36	−0.3941 (3)	0.3627 (3)	0.4797 (2)	0.0961 (12)
H36	−0.3558	0.3686	0.4254	0.115*
C37	−0.6735 (3)	0.2272 (4)	0.6640 (3)	0.1379 (18)
H37A	−0.7292	0.1883	0.6609	0.207*
H37B	−0.7155	0.2919	0.6782	0.207*
H37C	−0.6188	0.1956	0.7074	0.207*
C38	0.6624 (3)	0.1761 (3)	0.1948 (2)	0.0750 (10)
C39	0.6640 (3)	0.2563 (3)	0.2352 (2)	0.1141 (15)
H39	0.5938	0.3032	0.2470	0.137*
C40	0.7716 (3)	0.2665 (3)	0.2581 (2)	0.1103 (14)
H40	0.7740	0.3230	0.2821	0.132*
C41	0.8741 (3)	0.1953 (3)	0.24610 (19)	0.0739 (10)
C42	0.8717 (3)	0.1150 (3)	0.2073 (2)	0.0886 (11)
H42	0.9415	0.0669	0.1976	0.106*
C43	0.7637 (3)	0.1053 (3)	0.1821 (2)	0.0935 (12)
H43	0.7616	0.0499	0.1565	0.112*
C44	1.0825 (3)	0.1378 (2)	0.2661 (2)	0.0842 (10)
H44A	1.1459	0.1576	0.2882	0.126*
H44B	1.1024	0.1261	0.2070	0.126*
H44C	1.0713	0.0783	0.2993	0.126*
H1A	−0.302 (4)	0.518 (4)	0.577 (3)	0.20 (2)*
H2	0.571 (3)	0.109 (2)	0.1344 (19)	0.095 (11)*
H1	−0.023 (3)	0.352 (3)	0.313 (2)	0.133 (16)*
H4	−0.184 (3)	0.745 (3)	0.598 (2)	0.122 (18)*
H5	0.243 (2)	0.381 (2)	0.2898 (17)	0.071 (10)*
H8	0.397 (3)	0.023 (3)	−0.037 (2)	0.124 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0682 (13)	0.0589 (16)	0.0781 (14)	−0.0206 (12)	0.0069 (11)	−0.0238 (12)
O2	0.099 (2)	0.146 (3)	0.140 (3)	−0.063 (2)	−0.0104 (18)	0.017 (2)
O3	0.0750 (14)	0.0936 (19)	0.0625 (13)	−0.0130 (12)	0.0044 (11)	−0.0264 (12)
O4	0.0997 (19)	0.099 (2)	0.0850 (18)	−0.0209 (16)	0.0106 (15)	−0.0536 (16)
O5	0.0574 (13)	0.0986 (19)	0.0710 (14)	−0.0096 (12)	−0.0063 (11)	−0.0454 (14)
O6	0.0646 (14)	0.0966 (19)	0.1167 (18)	−0.0211 (14)	−0.0188 (13)	−0.0442 (15)
O7	0.0664 (14)	0.106 (2)	0.130 (2)	0.0146 (14)	−0.0295 (13)	−0.0754 (16)
O8	0.0720 (15)	0.0960 (19)	0.1022 (17)	0.0015 (14)	−0.0224 (13)	−0.0600 (15)
N1	0.0690 (18)	0.085 (2)	0.0626 (18)	−0.0132 (16)	0.0030 (15)	−0.0088 (16)
N2	0.0558 (17)	0.091 (2)	0.106 (2)	−0.0032 (16)	−0.0107 (14)	−0.0588 (19)
C1	0.0517 (17)	0.050 (2)	0.0596 (19)	−0.0086 (15)	−0.0007 (15)	−0.0118 (15)
C2	0.0550 (17)	0.055 (2)	0.0539 (18)	−0.0107 (16)	0.0007 (15)	−0.0152 (15)
C3	0.0634 (19)	0.074 (2)	0.0596 (19)	−0.0141 (18)	0.0024 (15)	−0.0169 (17)
C4	0.072 (2)	0.056 (2)	0.080 (2)	−0.0191 (17)	−0.0099 (18)	−0.0172 (18)
C5	0.083 (2)	0.063 (2)	0.061 (2)	−0.0160 (18)	−0.0017 (17)	−0.0223 (17)
C6	0.067 (2)	0.070 (2)	0.067 (2)	−0.0036 (18)	−0.0080 (17)	−0.0309 (18)
C7	0.0558 (19)	0.068 (2)	0.056 (2)	0.0051 (17)	−0.0085 (16)	−0.0172 (17)
C8	0.0521 (17)	0.060 (2)	0.0576 (18)	−0.0088 (16)	−0.0031 (15)	−0.0136 (16)
C9	0.0474 (16)	0.054 (2)	0.0570 (18)	−0.0038 (15)	−0.0039 (14)	−0.0151 (15)
C10	0.0609 (19)	0.057 (2)	0.063 (2)	−0.0113 (16)	−0.0017 (16)	−0.0186 (16)
C11	0.0543 (18)	0.067 (2)	0.0513 (17)	−0.0173 (16)	0.0010 (14)	−0.0202 (15)
C12	0.0559 (19)	0.065 (2)	0.0545 (18)	−0.0082 (16)	0.0002 (15)	−0.0191 (16)
C13	0.0612 (19)	0.061 (2)	0.0595 (18)	−0.0050 (16)	−0.0022 (15)	−0.0184 (16)
C14	0.064 (2)	0.085 (3)	0.0593 (19)	−0.0121 (18)	−0.0081 (15)	−0.0252 (18)
C15	0.0551 (18)	0.066 (2)	0.067 (2)	−0.0084 (17)	−0.0084 (15)	−0.0228 (17)
C16	0.062 (2)	0.074 (2)	0.074 (2)	−0.0143 (18)	−0.0047 (16)	−0.0385 (18)
C17	0.061 (2)	0.080 (3)	0.082 (2)	−0.0069 (19)	−0.0089 (17)	−0.040 (2)
C18	0.0492 (17)	0.070 (2)	0.0641 (19)	−0.0088 (16)	−0.0069 (14)	−0.0295 (17)
C19	0.0486 (17)	0.066 (2)	0.0601 (18)	−0.0123 (15)	0.0012 (14)	−0.0242 (16)
C20	0.0532 (18)	0.064 (2)	0.0594 (18)	−0.0062 (16)	−0.0010 (14)	−0.0234 (16)
C21	0.086 (2)	0.088 (3)	0.090 (2)	−0.034 (2)	0.026 (2)	−0.028 (2)
C22	0.0582 (18)	0.066 (2)	0.066 (2)	−0.0066 (17)	0.0035 (16)	−0.0186 (16)
C23	0.133 (3)	0.092 (3)	0.091 (3)	−0.053 (3)	0.019 (2)	−0.043 (2)
C24	0.125 (3)	0.111 (4)	0.168 (4)	−0.061 (3)	−0.048 (3)	−0.013 (3)
C25	0.273 (7)	0.104 (4)	0.234 (6)	−0.104 (5)	−0.152 (5)	0.065 (4)
C26	0.068 (2)	0.094 (3)	0.079 (2)	−0.0016 (19)	−0.0089 (17)	−0.026 (2)
C27	0.058 (2)	0.083 (3)	0.085 (2)	−0.0089 (18)	−0.0003 (17)	−0.0433 (19)
C28	0.076 (2)	0.118 (3)	0.086 (3)	0.005 (2)	−0.026 (2)	−0.052 (2)
C29	0.148 (4)	0.126 (4)	0.082 (3)	0.007 (3)	−0.035 (3)	−0.042 (2)
C30	0.101 (3)	0.199 (5)	0.166 (4)	−0.074 (3)	−0.020 (3)	−0.070 (4)
C31	0.060 (2)	0.085 (3)	0.073 (2)	−0.0167 (19)	0.0062 (18)	−0.0060 (19)
C32	0.099 (3)	0.129 (4)	0.080 (3)	−0.035 (3)	0.005 (2)	−0.002 (2)
C33	0.094 (3)	0.134 (4)	0.093 (3)	−0.046 (3)	0.010 (2)	0.006 (3)
C34	0.074 (2)	0.105 (4)	0.109 (3)	−0.032 (2)	0.002 (2)	0.012 (3)
C35	0.085 (3)	0.112 (4)	0.121 (3)	−0.045 (3)	0.003 (2)	−0.015 (3)
C36	0.086 (3)	0.114 (3)	0.094 (3)	−0.036 (2)	0.014 (2)	−0.025 (2)
C37	0.094 (3)	0.185 (5)	0.128 (4)	−0.057 (3)	−0.009 (3)	0.054 (3)
C38	0.0506 (18)	0.088 (3)	0.093 (2)	−0.0087 (18)	−0.0132 (16)	−0.047 (2)
C39	0.069 (2)	0.121 (3)	0.164 (4)	−0.003 (2)	−0.015 (2)	−0.097 (3)
C40	0.071 (2)	0.118 (3)	0.161 (4)	−0.016 (2)	−0.021 (2)	−0.088 (3)
C41	0.061 (2)	0.084 (3)	0.084 (2)	−0.0150 (19)	−0.0073 (17)	−0.037 (2)
C42	0.056 (2)	0.090 (3)	0.125 (3)	−0.0051 (19)	−0.0157 (19)	−0.051 (2)
C43	0.063 (2)	0.087 (3)	0.140 (3)	−0.007 (2)	−0.015 (2)	−0.068 (2)
C44	0.064 (2)	0.089 (3)	0.105 (3)	−0.020 (2)	−0.0120 (19)	−0.023 (2)

Geometric parameters (Å, º)

O1—C1	1.379 (3)	C21—H21B	0.9600
O1—H1	0.91 (4)	C21—H21C	0.9600
O2—C34	1.398 (4)	C22—H22	0.9300
O2—C37	1.413 (4)	C23—H23	0.9800
O3—C7	1.289 (3)	C23—C24	1.508 (4)
O4—C6	1.371 (3)	C23—C25	1.484 (5)
O4—H4	0.86 (3)	C24—H24A	0.9600
O5—C11	1.371 (3)	C24—H24B	0.9600
O5—H5	0.82 (3)	C24—H24C	0.9600
O6—C41	1.384 (3)	C25—H25A	0.9600
O6—C44	1.422 (3)	C25—H25B	0.9600
O7—C17	1.275 (3)	C25—H25C	0.9600
O8—C16	1.371 (3)	C26—H26A	0.9600
O8—H8	0.98 (3)	C26—H26B	0.9600
N1—C22	1.332 (4)	C26—H26C	0.9600
N1—C31	1.433 (4)	C27—H27	0.9300
N1—H1A	0.95 (5)	C28—H28	0.9800
N2—C27	1.319 (4)	C28—C29	1.514 (4)
N2—C38	1.441 (4)	C28—C30	1.521 (5)
N2—H2	0.92 (3)	C29—H29A	0.9600
C1—C2	1.376 (3)	C29—H29B	0.9600
C1—C9	1.417 (3)	C29—H29C	0.9600
C2—C3	1.403 (4)	C30—H30A	0.9600
C2—C12	1.502 (4)	C30—H30B	0.9600
C3—C4	1.376 (4)	C30—H30C	0.9600
C3—C21	1.513 (4)	C31—C32	1.373 (4)
C4—H4A	0.9300	C31—C36	1.391 (4)
C4—C10	1.404 (4)	C32—H32	0.9300
C5—C6	1.353 (4)	C32—C33	1.409 (5)
C5—C10	1.450 (4)	C33—H33	0.9300
C5—C23	1.516 (5)	C33—C34	1.354 (5)
C6—C7	1.446 (4)	C34—C35	1.367 (5)
C7—C8	1.426 (4)	C35—H35	0.9300
C8—C9	1.456 (4)	C35—C36	1.368 (5)
C8—C22	1.390 (4)	C36—H36	0.9300
C9—C10	1.428 (4)	C37—H37A	0.9600
C11—C12	1.376 (4)	C37—H37B	0.9600
C11—C19	1.414 (3)	C37—H37C	0.9600
C12—C13	1.415 (4)	C38—C39	1.369 (4)
C13—C14	1.376 (3)	C38—C43	1.353 (4)
C13—C26	1.502 (4)	C39—H39	0.9300
C14—H14	0.9300	C39—C40	1.383 (4)
C14—C20	1.397 (4)	C40—H40	0.9300
C15—C16	1.336 (4)	C40—C41	1.364 (4)
C15—C20	1.449 (3)	C41—C42	1.359 (4)
C15—C28	1.532 (4)	C42—H42	0.9300
C16—C17	1.476 (4)	C42—C43	1.398 (4)
C17—C18	1.409 (4)	C43—H43	0.9300
C18—C19	1.445 (4)	C44—H44A	0.9600
C18—C27	1.423 (4)	C44—H44B	0.9600
C19—C20	1.431 (4)	C44—H44C	0.9600
C21—H21A	0.9600
C1—O1—H1	114 (2)	C23—C24—H24A	109.5
C34—O2—C37	116.4 (4)	C23—C24—H24B	109.5
C6—O4—H4	107 (3)	C23—C24—H24C	109.5
C11—O5—H5	110 (2)	H24A—C24—H24B	109.5
C41—O6—C44	116.8 (2)	H24A—C24—H24C	109.5
C16—O8—H8	117 (2)	H24B—C24—H24C	109.5
C22—N1—C31	126.7 (3)	C23—C25—H25A	109.5
C22—N1—H1A	121 (3)	C23—C25—H25B	109.5
C31—N1—H1A	112 (3)	C23—C25—H25C	109.5
C27—N2—C38	126.5 (3)	H25A—C25—H25B	109.5
C27—N2—H2	122 (2)	H25A—C25—H25C	109.5
C38—N2—H2	111 (2)	H25B—C25—H25C	109.5
O1—C1—C9	117.2 (3)	C13—C26—H26A	109.5
C2—C1—O1	119.0 (2)	C13—C26—H26B	109.5
C2—C1—C9	123.8 (3)	C13—C26—H26C	109.5
C1—C2—C3	119.4 (3)	H26A—C26—H26B	109.5
C1—C2—C12	120.3 (3)	H26A—C26—H26C	109.5
C3—C2—C12	120.2 (3)	H26B—C26—H26C	109.5
C2—C3—C21	121.4 (3)	N2—C27—C18	123.6 (3)
C4—C3—C2	117.8 (3)	N2—C27—H27	118.2
C4—C3—C21	120.7 (3)	C18—C27—H27	118.2
C3—C4—H4A	117.8	C15—C28—H28	106.9
C3—C4—C10	124.3 (3)	C29—C28—C15	113.3 (3)
C10—C4—H4A	117.8	C29—C28—H28	106.9
C6—C5—C10	117.5 (3)	C29—C28—C30	112.2 (3)
C6—C5—C23	120.2 (3)	C30—C28—C15	110.2 (3)
C10—C5—C23	122.3 (3)	C30—C28—H28	106.9
O4—C6—C7	113.5 (3)	C28—C29—H29A	109.5
C5—C6—O4	122.6 (3)	C28—C29—H29B	109.5
C5—C6—C7	123.9 (3)	C28—C29—H29C	109.5
O3—C7—C6	116.7 (3)	H29A—C29—H29B	109.5
O3—C7—C8	124.1 (3)	H29A—C29—H29C	109.5
C8—C7—C6	119.2 (3)	H29B—C29—H29C	109.5
C7—C8—C9	118.4 (3)	C28—C30—H30A	109.5
C22—C8—C7	117.8 (3)	C28—C30—H30B	109.5
C22—C8—C9	123.8 (3)	C28—C30—H30C	109.5
C1—C9—C8	124.3 (3)	H30A—C30—H30B	109.5
C1—C9—C10	116.4 (3)	H30A—C30—H30C	109.5
C10—C9—C8	119.2 (2)	H30B—C30—H30C	109.5
C4—C10—C5	120.2 (3)	C32—C31—N1	117.3 (3)
C4—C10—C9	118.1 (3)	C32—C31—C36	119.3 (4)
C9—C10—C5	121.7 (3)	C36—C31—N1	123.2 (3)
O5—C11—C12	120.1 (2)	C31—C32—H32	119.8
O5—C11—C19	116.3 (2)	C31—C32—C33	120.4 (4)
C12—C11—C19	123.6 (2)	C33—C32—H32	119.8
C11—C12—C2	120.2 (2)	C32—C33—H33	120.6
C11—C12—C13	119.1 (2)	C34—C33—C32	118.7 (4)
C13—C12—C2	120.7 (2)	C34—C33—H33	120.6
C12—C13—C26	121.7 (2)	C33—C34—O2	124.0 (4)
C14—C13—C12	117.6 (3)	C33—C34—C35	121.3 (4)
C14—C13—C26	120.7 (3)	C35—C34—O2	114.7 (4)
C13—C14—H14	117.6	C34—C35—H35	119.7
C13—C14—C20	124.8 (3)	C34—C35—C36	120.5 (4)
C20—C14—H14	117.6	C36—C35—H35	119.7
C16—C15—C20	119.2 (3)	C31—C36—H36	120.1
C16—C15—C28	119.3 (3)	C35—C36—C31	119.7 (4)
C20—C15—C28	121.4 (3)	C35—C36—H36	120.1
O8—C16—C17	113.5 (3)	O2—C37—H37A	109.5
C15—C16—O8	123.2 (3)	O2—C37—H37B	109.5
C15—C16—C17	123.4 (3)	O2—C37—H37C	109.5
O7—C17—C16	116.9 (3)	H37A—C37—H37B	109.5
O7—C17—C18	126.0 (3)	H37A—C37—H37C	109.5
C18—C17—C16	117.1 (3)	H37B—C37—H37C	109.5
C17—C18—C19	120.7 (2)	C39—C38—N2	122.5 (3)
C17—C18—C27	116.1 (2)	C43—C38—N2	117.3 (3)
C27—C18—C19	122.7 (2)	C43—C38—C39	120.2 (3)
C11—C19—C18	124.1 (2)	C38—C39—H39	120.5
C11—C19—C20	117.1 (2)	C38—C39—C40	119.0 (3)
C20—C19—C18	118.7 (2)	C40—C39—H39	120.5
C14—C20—C15	122.2 (3)	C39—C40—H40	119.5
C14—C20—C19	117.6 (2)	C41—C40—C39	121.1 (3)
C19—C20—C15	120.2 (2)	C41—C40—H40	119.5
C3—C21—H21A	109.5	C40—C41—O6	115.6 (3)
C3—C21—H21B	109.5	C42—C41—O6	124.7 (3)
C3—C21—H21C	109.5	C42—C41—C40	119.5 (3)
H21A—C21—H21B	109.5	C41—C42—H42	120.2
H21A—C21—H21C	109.5	C41—C42—C43	119.6 (3)
H21B—C21—H21C	109.5	C43—C42—H42	120.2
N1—C22—C8	123.5 (3)	C38—C43—C42	120.3 (3)
N1—C22—H22	118.3	C38—C43—H43	119.8
C8—C22—H22	118.3	C42—C43—H43	119.8
C5—C23—H23	105.6	O6—C44—H44A	109.5
C24—C23—C5	115.0 (3)	O6—C44—H44B	109.5
C24—C23—H23	105.6	O6—C44—H44C	109.5
C25—C23—C5	113.6 (4)	H44A—C44—H44B	109.5
C25—C23—H23	105.6	H44A—C44—H44C	109.5
C25—C23—C24	110.6 (3)	H44B—C44—H44C	109.5
O1—C1—C2—C3	−177.8 (3)	C12—C11—C19—C18	179.5 (3)
O1—C1—C2—C12	1.6 (4)	C12—C11—C19—C20	−4.0 (5)
O1—C1—C9—C8	−1.1 (4)	C12—C13—C14—C20	−3.7 (5)
O1—C1—C9—C10	177.2 (2)	C13—C14—C20—C15	179.4 (3)
O2—C34—C35—C36	−179.2 (4)	C13—C14—C20—C19	1.0 (5)
O3—C7—C8—C9	−177.9 (2)	C15—C16—C17—O7	−178.8 (3)
O3—C7—C8—C22	6.1 (4)	C15—C16—C17—C18	−0.6 (5)
O4—C6—C7—O3	−3.1 (4)	C16—C15—C20—C14	−173.1 (3)
O4—C6—C7—C8	174.5 (3)	C16—C15—C20—C19	5.2 (5)
O5—C11—C12—C2	5.0 (4)	C16—C15—C28—C29	−55.0 (5)
O5—C11—C12—C13	−177.7 (3)	C16—C15—C28—C30	71.5 (4)
O5—C11—C19—C18	−1.5 (5)	C16—C17—C18—C19	7.1 (5)
O5—C11—C19—C20	175.0 (3)	C16—C17—C18—C27	−165.5 (3)
O6—C41—C42—C43	−178.1 (3)	C17—C18—C19—C11	169.1 (3)
O7—C17—C18—C19	−174.9 (3)	C17—C18—C19—C20	−7.3 (5)
O7—C17—C18—C27	12.5 (5)	C17—C18—C27—N2	−6.9 (5)
O8—C16—C17—O7	−1.0 (5)	C18—C19—C20—C14	179.5 (3)
O8—C16—C17—C18	177.2 (3)	C18—C19—C20—C15	1.1 (5)
N1—C31—C32—C33	178.5 (3)	C19—C11—C12—C2	−176.0 (3)
N1—C31—C36—C35	−177.9 (3)	C19—C11—C12—C13	1.3 (5)
N2—C38—C39—C40	−176.7 (4)	C19—C18—C27—N2	−179.3 (3)
N2—C38—C43—C42	178.2 (3)	C20—C15—C16—O8	176.9 (3)
C1—C2—C3—C4	−0.9 (4)	C20—C15—C16—C17	−5.5 (5)
C1—C2—C3—C21	−177.7 (3)	C20—C15—C28—C29	125.8 (3)
C1—C2—C12—C11	−107.7 (3)	C20—C15—C28—C30	−107.6 (4)
C1—C2—C12—C13	75.0 (4)	C21—C3—C4—C10	176.5 (3)
C1—C9—C10—C4	2.1 (4)	C22—N1—C31—C32	169.9 (3)
C1—C9—C10—C5	−178.4 (3)	C22—N1—C31—C36	−14.6 (5)
C2—C1—C9—C8	178.3 (3)	C22—C8—C9—C1	−8.7 (4)
C2—C1—C9—C10	−3.4 (4)	C22—C8—C9—C10	173.1 (3)
C2—C3—C4—C10	−0.3 (5)	C23—C5—C6—O4	0.4 (5)
C2—C12—C13—C14	179.8 (3)	C23—C5—C6—C7	179.0 (3)
C2—C12—C13—C26	−2.3 (5)	C23—C5—C10—C4	2.7 (5)
C3—C2—C12—C11	71.7 (4)	C23—C5—C10—C9	−176.8 (3)
C3—C2—C12—C13	−105.6 (3)	C26—C13—C14—C20	178.4 (3)
C3—C4—C10—C5	−179.9 (3)	C27—N2—C38—C39	4.3 (6)
C3—C4—C10—C9	−0.3 (4)	C27—N2—C38—C43	−176.1 (3)
C5—C6—C7—O3	178.2 (3)	C27—C18—C19—C11	−18.8 (5)
C5—C6—C7—C8	−4.3 (5)	C27—C18—C19—C20	164.8 (3)
C6—C5—C10—C4	−179.8 (3)	C28—C15—C16—O8	−2.3 (5)
C6—C5—C10—C9	0.7 (4)	C28—C15—C16—C17	175.3 (3)
C6—C5—C23—C24	54.8 (5)	C28—C15—C20—C14	6.0 (5)
C6—C5—C23—C25	−74.1 (4)	C28—C15—C20—C19	−175.6 (3)
C6—C7—C8—C9	4.7 (4)	C31—N1—C22—C8	175.1 (3)
C6—C7—C8—C22	−171.3 (3)	C31—C32—C33—C34	−0.8 (6)
C7—C8—C9—C1	175.5 (3)	C32—C31—C36—C35	−2.5 (6)
C7—C8—C9—C10	−2.7 (4)	C32—C33—C34—O2	179.6 (4)
C7—C8—C22—N1	−4.3 (4)	C32—C33—C34—C35	−1.5 (7)
C8—C9—C10—C4	−179.5 (3)	C33—C34—C35—C36	1.8 (6)
C8—C9—C10—C5	0.0 (4)	C34—C35—C36—C31	0.2 (6)
C9—C1—C2—C3	2.9 (4)	C36—C31—C32—C33	2.8 (6)
C9—C1—C2—C12	−177.7 (3)	C37—O2—C34—C33	0.8 (6)
C9—C8—C22—N1	179.9 (3)	C37—O2—C34—C35	−178.2 (3)
C10—C5—C6—O4	−177.2 (3)	C38—N2—C27—C18	170.9 (3)
C10—C5—C6—C7	1.5 (5)	C38—C39—C40—C41	−4.2 (7)
C10—C5—C23—C24	−127.8 (3)	C39—C38—C43—C42	−2.2 (6)
C10—C5—C23—C25	103.3 (4)	C39—C40—C41—O6	180.0 (4)
C11—C12—C13—C14	2.5 (5)	C39—C40—C41—C42	3.1 (6)
C11—C12—C13—C26	−179.6 (3)	C40—C41—C42—C43	−1.6 (6)
C11—C19—C20—C14	2.8 (4)	C41—C42—C43—C38	1.1 (6)
C11—C19—C20—C15	−175.6 (3)	C43—C38—C39—C40	3.7 (6)
C12—C2—C3—C4	179.7 (3)	C44—O6—C41—C40	175.3 (3)
C12—C2—C3—C21	2.9 (4)	C44—O6—C41—C42	−8.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.95 (5)	1.83 (5)	2.538 (4)	129 (4)
N2—H2···O7	0.92 (3)	1.87 (3)	2.550 (3)	129 (3)
O1—H1···O6^i	0.91 (4)	2.13 (4)	2.912 (3)	144 (3)
O4—H4···O3	0.86 (3)	2.04 (4)	2.574 (4)	119 (3)
O5—H5···O3^ii	0.82 (3)	1.98 (3)	2.684 (3)	143 (3)
O8—H8···O7	0.98 (3)	2.17 (3)	2.601 (3)	105 (2)
O8—H8···O7^iii	0.98 (3)	1.83 (3)	2.757 (3)	158 (3)

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