(S,S)-6,6′-Dimethyl-2,2′-[o-phenylenebis(nitrilomethylidyne)]diphenol benzene solvate

The asymmetric unit of the title compound, C₂₂H₂₆N₂O₂·C₆H₆, contains two mol­ecules of N,N′-bis­(3-methyl­salicyl­idene)cyclo­hexane-1,2-diamine {or 6,6′-dimethyl-2,2′-[o-phenylene­bis(nitrilomethylidene)]diphenol} and two benzene mol­ecules. There are two intra­molecular O—H...N bonds in each of the independent salicyl­idene mol­ecules; each of them closes a six-membered pseudo-ring. The packing of the crystal structure features stacks of alternating cyclo­hexane fragments and benzene mol­ecules running along the short a axis.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.057
• wR factor = 0.151
• Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.068
            Value of mu given      =     0.070
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.00
           From the CIF: _reflns_number_total               5788
           Count of symmetry unique reflns         5815
           Completeness (_total/calc)             99.54%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C28    = .          S

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

   6 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(S,S)-6,6'-Dimethyl-2,2'-[o-phenylenebis(nitrilomethylidyne)]diphenol benzene solvate

Crystal data

C22H26N2O2·C6H6	F(000) = 920
Mr = 428.56	Dx = 1.093 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 850 reflections
a = 8.2760 (18) Å	θ = 2.5–19.1°
b = 26.636 (6) Å	µ = 0.07 mm^−1
c = 12.250 (3) Å	T = 291 K
β = 105.250 (3)°	Block, yellow
V = 2605.4 (10) Å^3	0.32 × 0.26 × 0.24 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5788 independent reflections
Radiation source: sealed tube	4361 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→9
Tmin = 0.978, Tmax = 0.984	k = −34→33
15086 measured reflections	l = −15→15

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0844P)^2 + 0.1157P] where P = (Fo^2 + 2Fc^2)/3
5788 reflections	(Δ/σ)max = 0.001
597 parameters	Δρmax = 0.26 e Å^−3
1 restraint	Δρmin = −0.22 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	0.0245 (6)	0.58090 (17)	0.6989 (3)	0.0575 (10)
H1	−0.0882	0.5784	0.7101	0.069*
C2	0.0097 (5)	0.58883 (16)	0.5716 (3)	0.0531 (9)
H2A	−0.0566	0.6188	0.5479	0.064*
H2B	0.1212	0.5956	0.5635	0.064*
C3	−0.0626 (5)	0.54864 (17)	0.4923 (4)	0.0560 (10)
H3A	−0.0474	0.5562	0.4182	0.067*
H3B	−0.1818	0.5460	0.4854	0.067*
C4	0.0268 (6)	0.49716 (18)	0.5372 (4)	0.0591 (10)
H4A	−0.0333	0.4702	0.4905	0.071*
H4B	0.1392	0.4979	0.5272	0.071*
C5	0.0390 (5)	0.48464 (16)	0.6630 (3)	0.0543 (9)
H5A	−0.0718	0.4787	0.6732	0.065*
H5B	0.1060	0.4547	0.6859	0.065*
C6	0.1196 (5)	0.52901 (15)	0.7335 (3)	0.0515 (9)
H6	0.2364	0.5322	0.7305	0.062*
C7	0.0506 (5)	0.64376 (15)	0.8439 (3)	0.0513 (9)
H7	−0.0543	0.6349	0.8521	0.062*
C8	0.1409 (5)	0.68183 (16)	0.9110 (3)	0.0526 (9)
C9	0.0734 (5)	0.70576 (16)	0.9899 (4)	0.0541 (9)
H9	−0.0348	0.6982	0.9936	0.065*
C10	0.1689 (6)	0.74112 (17)	1.0633 (4)	0.0569 (10)
H10	0.1245	0.7575	1.1159	0.068*
C11	0.3317 (6)	0.75183 (18)	1.0572 (4)	0.0617 (11)
H11	0.3956	0.7752	1.1066	0.074*
C12	0.3994 (5)	0.72793 (19)	0.9783 (3)	0.0611 (11)
C13	0.3027 (5)	0.69261 (17)	0.9058 (4)	0.0567 (10)
C14	0.5710 (5)	0.74251 (17)	0.9642 (3)	0.0548 (9)
H14A	0.5707	0.7774	0.9448	0.082*
H14B	0.5954	0.7227	0.9050	0.082*
H14C	0.6547	0.7365	1.0337	0.082*
C15	0.2463 (6)	0.51743 (17)	0.9325 (4)	0.0584 (10)
H15	0.3473	0.5235	0.9151	0.070*
C16	0.2514 (5)	0.50663 (16)	1.0449 (3)	0.0535 (10)
C17	0.4042 (5)	0.50588 (15)	1.1284 (4)	0.0589 (11)
H17	0.5030	0.5134	1.1092	0.071*
C18	0.4089 (5)	0.49416 (16)	1.2384 (4)	0.0584 (10)
H18	0.5102	0.4947	1.2938	0.070*
C19	0.2626 (5)	0.48155 (15)	1.2669 (3)	0.0521 (9)
H19	0.2670	0.4728	1.3411	0.063*
C20	0.1106 (5)	0.48181 (15)	1.1863 (3)	0.0508 (9)
C21	0.1051 (5)	0.49472 (16)	1.0758 (3)	0.0554 (10)
C22	−0.0497 (5)	0.46954 (16)	1.2181 (3)	0.0527 (9)
H22A	−0.1166	0.4993	1.2129	0.079*
H22B	−0.0232	0.4570	1.2942	0.079*
H22C	−0.1111	0.4445	1.1674	0.079*
C23	0.1568 (5)	0.31680 (16)	0.4865 (3)	0.0517 (9)
H23	0.0354	0.3145	0.4757	0.062*
C24	0.1912 (6)	0.35604 (17)	0.4028 (3)	0.0562 (10)
H24A	0.3108	0.3614	0.4170	0.067*
H24B	0.1396	0.3878	0.4133	0.067*
C25	0.1185 (5)	0.33725 (16)	0.2798 (3)	0.0526 (9)
H25A	−0.0021	0.3337	0.2642	0.063*
H25B	0.1422	0.3615	0.2270	0.063*
C26	0.1982 (5)	0.28600 (16)	0.2644 (4)	0.0543 (10)
H26A	0.1604	0.2756	0.1859	0.065*
H26B	0.3191	0.2893	0.2837	0.065*
C27	0.1494 (5)	0.24634 (16)	0.3398 (3)	0.0532 (9)
H27A	0.1956	0.2140	0.3276	0.064*
H27B	0.0285	0.2433	0.3222	0.064*
C28	0.2233 (5)	0.26381 (15)	0.4693 (3)	0.0517 (9)
H28	0.3460	0.2644	0.4880	0.062*
C29	0.1368 (6)	0.33765 (17)	0.6693 (4)	0.0579 (10)
H29	0.0229	0.3311	0.6416	0.069*
C30	0.1993 (6)	0.35245 (18)	0.7864 (4)	0.0584 (10)
C31	0.0911 (5)	0.35568 (16)	0.8537 (3)	0.0521 (9)
H31	−0.0215	0.3481	0.8236	0.063*
C32	0.1473 (5)	0.37015 (15)	0.9661 (3)	0.0494 (9)
H32	0.0730	0.3719	1.0113	0.059*
C33	0.3156 (5)	0.38208 (17)	1.0108 (4)	0.0586 (10)
H33	0.3539	0.3919	1.0861	0.070*
C34	0.4280 (5)	0.37932 (15)	0.9423 (3)	0.0504 (9)
C35	0.3688 (5)	0.36432 (15)	0.8298 (3)	0.0520 (9)
C36	0.6094 (5)	0.39302 (16)	0.9899 (3)	0.0547 (10)
H36A	0.6727	0.3633	1.0178	0.082*
H36B	0.6195	0.4165	1.0507	0.082*
H36C	0.6517	0.4079	0.9316	0.082*
C37	0.2862 (6)	0.20715 (16)	0.6262 (3)	0.0557 (10)
H37	0.3990	0.2138	0.6339	0.067*
C38	0.2376 (5)	0.17351 (16)	0.7025 (4)	0.0551 (9)
C39	0.3639 (6)	0.15020 (16)	0.7864 (3)	0.0549 (10)
H39	0.4762	0.1557	0.7901	0.066*
C40	0.3187 (6)	0.11887 (16)	0.8637 (4)	0.0555 (10)
H40	0.4021	0.1041	0.9206	0.067*
C41	0.1518 (6)	0.10897 (16)	0.8586 (4)	0.0579 (10)
H41	0.1233	0.0874	0.9102	0.069*
C42	0.0281 (5)	0.13231 (17)	0.7737 (3)	0.0546 (9)
C43	0.0702 (5)	0.16457 (15)	0.6960 (3)	0.0508 (9)
C44	−0.1635 (5)	0.12319 (15)	0.7656 (3)	0.0493 (9)
H44A	−0.1738	0.0980	0.8195	0.074*
H44B	−0.2197	0.1121	0.6907	0.074*
H44C	−0.2132	0.1539	0.7817	0.074*
C45	0.5927 (6)	0.54655 (17)	0.7888 (4)	0.0605 (11)
H45	0.6325	0.5570	0.8636	0.073*
C46	0.5541 (5)	0.58216 (16)	0.7012 (4)	0.0551 (10)
H46	0.5718	0.6161	0.7176	0.066*
C47	0.4898 (6)	0.56670 (16)	0.5908 (4)	0.0567 (10)
H47	0.4619	0.5902	0.5327	0.068*
C48	0.4671 (6)	0.51568 (19)	0.5672 (4)	0.0678 (13)
H48	0.4245	0.5052	0.4927	0.081*
C49	0.5066 (5)	0.48052 (16)	0.6520 (4)	0.0574 (10)
H49	0.4901	0.4466	0.6351	0.069*
C50	0.5717 (5)	0.49615 (16)	0.7640 (4)	0.0544 (10)
H50	0.6009	0.4725	0.8217	0.065*
C51	0.6987 (5)	0.32238 (16)	0.5483 (4)	0.0562 (10)
H51	0.7057	0.3325	0.6221	0.067*
C52	0.6847 (5)	0.35812 (18)	0.4627 (4)	0.0616 (11)
H52	0.6810	0.3921	0.4793	0.074*
C53	0.6763 (5)	0.34285 (16)	0.3521 (4)	0.0542 (10)
H53	0.6683	0.3666	0.2953	0.065*
C54	0.6798 (5)	0.29232 (16)	0.3278 (4)	0.0602 (11)
H54	0.6728	0.2821	0.2541	0.072*
C55	0.6938 (5)	0.25641 (17)	0.4126 (3)	0.0533 (9)
H55	0.6976	0.2225	0.3957	0.064*
C56	0.7022 (5)	0.27147 (16)	0.5222 (4)	0.0582 (10)
H56	0.7101	0.2475	0.5786	0.070*
N1	0.1126 (4)	0.61985 (13)	0.7680 (3)	0.0537 (8)
N2	0.1134 (4)	0.51953 (13)	0.8526 (3)	0.0494 (7)
N3	0.2318 (4)	0.33302 (13)	0.6009 (3)	0.0539 (8)
N4	0.1688 (4)	0.22902 (13)	0.5435 (3)	0.0519 (8)
O1	0.3890 (4)	0.67036 (12)	0.8424 (3)	0.0583 (7)
H1E	0.339 (6)	0.643 (2)	0.818 (4)	0.058 (13)*
O2	−0.0432 (3)	0.49383 (11)	0.9999 (3)	0.0551 (7)
H2E	−0.029 (7)	0.498 (2)	0.933 (5)	0.083 (18)*
O3	0.4748 (4)	0.36165 (11)	0.7640 (3)	0.0533 (7)
H3E	0.418 (7)	0.363 (2)	0.696 (4)	0.066 (15)*
O4	−0.0438 (4)	0.18528 (11)	0.6124 (3)	0.0583 (7)
H4E	−0.005 (6)	0.1946 (17)	0.556 (4)	0.049 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.062 (3)	0.059 (2)	0.050 (2)	0.007 (2)	0.0130 (19)	0.0018 (19)
C2	0.056 (2)	0.050 (2)	0.054 (2)	0.0131 (18)	0.0175 (18)	0.0163 (18)
C3	0.051 (2)	0.061 (2)	0.057 (2)	0.0036 (19)	0.0146 (19)	0.003 (2)
C4	0.054 (2)	0.060 (2)	0.067 (3)	0.0058 (19)	0.023 (2)	−0.004 (2)
C5	0.052 (2)	0.056 (2)	0.056 (2)	−0.0057 (18)	0.0144 (18)	−0.0125 (18)
C6	0.056 (2)	0.053 (2)	0.047 (2)	−0.0042 (18)	0.0172 (18)	0.0069 (17)
C7	0.043 (2)	0.052 (2)	0.056 (2)	0.0092 (17)	0.0087 (17)	0.0039 (18)
C8	0.050 (2)	0.052 (2)	0.054 (2)	−0.0020 (17)	0.0108 (18)	−0.0012 (17)
C9	0.053 (2)	0.051 (2)	0.056 (2)	0.0116 (17)	0.0112 (18)	−0.0007 (18)
C10	0.057 (2)	0.057 (2)	0.053 (2)	0.0058 (19)	0.0085 (18)	−0.0095 (19)
C11	0.055 (2)	0.063 (3)	0.057 (2)	0.005 (2)	−0.0041 (19)	0.001 (2)
C12	0.052 (2)	0.073 (3)	0.047 (2)	−0.015 (2)	−0.0069 (17)	−0.004 (2)
C13	0.050 (2)	0.059 (2)	0.059 (2)	−0.0119 (18)	0.0106 (18)	−0.0092 (19)
C14	0.054 (2)	0.060 (2)	0.047 (2)	−0.0108 (19)	0.0061 (17)	−0.0167 (18)
C15	0.062 (3)	0.058 (2)	0.053 (2)	−0.009 (2)	0.0111 (19)	−0.0119 (19)
C16	0.051 (2)	0.061 (2)	0.0447 (19)	−0.0040 (18)	0.0057 (17)	−0.0117 (17)
C17	0.053 (2)	0.053 (2)	0.054 (2)	−0.0148 (17)	−0.0156 (18)	−0.0109 (18)
C18	0.054 (2)	0.048 (2)	0.059 (2)	−0.0106 (18)	−0.0102 (19)	−0.0129 (18)
C19	0.053 (2)	0.049 (2)	0.045 (2)	−0.0113 (17)	−0.0045 (16)	−0.0134 (16)
C20	0.048 (2)	0.051 (2)	0.051 (2)	−0.0046 (17)	0.0092 (16)	−0.0046 (17)
C21	0.054 (2)	0.054 (2)	0.051 (2)	−0.0069 (18)	0.0007 (18)	−0.0098 (18)
C22	0.055 (2)	0.057 (2)	0.047 (2)	−0.0167 (18)	0.0136 (17)	0.0032 (17)
C23	0.048 (2)	0.054 (2)	0.052 (2)	−0.0082 (17)	0.0115 (17)	−0.0086 (17)
C24	0.060 (2)	0.057 (2)	0.052 (2)	−0.0200 (19)	0.0159 (18)	−0.0053 (18)
C25	0.053 (2)	0.057 (2)	0.048 (2)	−0.0098 (18)	0.0132 (17)	0.0034 (17)
C26	0.054 (2)	0.057 (2)	0.053 (2)	−0.0109 (18)	0.0143 (18)	−0.0148 (18)
C27	0.057 (2)	0.057 (2)	0.0459 (19)	−0.0096 (18)	0.0139 (17)	−0.0170 (18)
C28	0.053 (2)	0.049 (2)	0.052 (2)	−0.0120 (17)	0.0119 (18)	−0.0035 (17)
C29	0.054 (2)	0.061 (2)	0.054 (2)	0.0145 (19)	0.0069 (18)	−0.0018 (19)
C30	0.052 (2)	0.065 (3)	0.054 (2)	−0.0017 (19)	0.0062 (18)	−0.0042 (19)
C31	0.057 (2)	0.051 (2)	0.050 (2)	−0.0020 (18)	0.0157 (18)	−0.0014 (17)
C32	0.055 (2)	0.050 (2)	0.0469 (19)	0.0141 (17)	0.0207 (17)	−0.0147 (16)
C33	0.053 (2)	0.063 (3)	0.056 (2)	0.0077 (19)	0.0086 (19)	0.009 (2)
C34	0.049 (2)	0.046 (2)	0.0445 (19)	−0.0121 (16)	−0.0079 (16)	−0.0057 (16)
C35	0.049 (2)	0.047 (2)	0.053 (2)	−0.0024 (17)	0.0024 (17)	−0.0069 (17)
C36	0.050 (2)	0.051 (2)	0.048 (2)	−0.0105 (17)	−0.0142 (17)	−0.0171 (17)
C37	0.055 (2)	0.057 (2)	0.053 (2)	0.0087 (18)	0.0124 (18)	−0.0133 (18)
C38	0.052 (2)	0.051 (2)	0.057 (2)	0.0102 (18)	0.0050 (18)	−0.0036 (18)
C39	0.052 (2)	0.051 (2)	0.056 (2)	0.0115 (18)	0.0048 (18)	0.0054 (18)
C40	0.062 (2)	0.049 (2)	0.053 (2)	0.0146 (19)	0.0108 (18)	0.0104 (17)
C41	0.061 (3)	0.053 (2)	0.052 (2)	−0.0081 (18)	0.0015 (18)	0.0156 (18)
C42	0.052 (2)	0.058 (2)	0.053 (2)	−0.0068 (18)	0.0124 (18)	0.0066 (18)
C43	0.052 (2)	0.051 (2)	0.052 (2)	−0.0015 (17)	0.0183 (18)	−0.0029 (17)
C44	0.051 (2)	0.047 (2)	0.0496 (19)	−0.0185 (17)	0.0123 (17)	0.0106 (16)
C45	0.059 (2)	0.055 (2)	0.058 (2)	−0.0037 (19)	−0.0018 (19)	0.0138 (19)
C46	0.057 (2)	0.048 (2)	0.062 (2)	−0.0163 (18)	0.020 (2)	−0.0182 (18)
C47	0.058 (2)	0.052 (2)	0.063 (2)	0.0203 (18)	0.022 (2)	0.0219 (19)
C48	0.053 (2)	0.065 (3)	0.068 (3)	−0.019 (2)	−0.014 (2)	0.014 (2)
C49	0.058 (2)	0.049 (2)	0.064 (2)	0.0216 (18)	0.0135 (19)	−0.0167 (19)
C50	0.059 (2)	0.051 (2)	0.056 (2)	0.0194 (19)	0.0196 (19)	0.0084 (18)
C51	0.051 (2)	0.057 (2)	0.058 (2)	−0.0099 (18)	0.0090 (18)	0.0249 (19)
C52	0.057 (2)	0.056 (2)	0.055 (2)	−0.0145 (19)	−0.0144 (18)	0.0137 (19)
C53	0.041 (2)	0.061 (2)	0.056 (2)	−0.0147 (17)	0.0045 (17)	−0.0143 (19)
C54	0.052 (2)	0.053 (2)	0.061 (2)	−0.0151 (18)	−0.0113 (19)	0.0097 (19)
C55	0.048 (2)	0.059 (2)	0.052 (2)	−0.0055 (17)	0.0114 (17)	0.0164 (18)
C56	0.056 (2)	0.053 (2)	0.064 (3)	−0.0116 (19)	0.015 (2)	0.010 (2)
N1	0.0556 (19)	0.0545 (19)	0.0509 (17)	−0.0163 (15)	0.0139 (15)	0.0042 (15)
N2	0.0518 (18)	0.0519 (17)	0.0431 (16)	0.0002 (14)	0.0101 (14)	−0.0005 (14)
N3	0.0536 (19)	0.0480 (18)	0.0559 (19)	−0.0148 (15)	0.0071 (16)	0.0001 (15)
N4	0.0574 (19)	0.0508 (18)	0.0484 (17)	−0.0052 (15)	0.0154 (15)	−0.0147 (15)
O1	0.0573 (17)	0.0581 (18)	0.0623 (17)	−0.0200 (14)	0.0207 (14)	−0.0164 (14)
O2	0.0501 (16)	0.0561 (16)	0.0553 (17)	−0.0135 (13)	0.0073 (14)	−0.0070 (13)
O3	0.0514 (16)	0.0511 (16)	0.0567 (17)	−0.0142 (12)	0.0128 (14)	−0.0052 (13)
O4	0.0563 (17)	0.0515 (16)	0.0564 (17)	−0.0017 (13)	−0.0039 (14)	−0.0075 (13)

Geometric parameters (Å, º)

C1—N1	1.414 (6)	C27—H27A	0.9700
C1—C2	1.546 (6)	C27—H27B	0.9700
C1—C6	1.592 (6)	C28—N4	1.451 (5)
C1—H1	0.9800	C28—H28	0.9800
C2—C3	1.464 (6)	C29—N3	1.297 (6)
C2—H2A	0.9700	C29—C30	1.447 (6)
C2—H2B	0.9700	C29—H29	0.9300
C3—C4	1.586 (6)	C30—C31	1.370 (6)
C3—H3A	0.9700	C30—C35	1.400 (6)
C3—H3B	0.9700	C31—C32	1.387 (5)
C4—C5	1.555 (6)	C31—H31	0.9300
C4—H4A	0.9700	C32—C33	1.393 (6)
C4—H4B	0.9700	C32—H32	0.9300
C5—C6	1.511 (6)	C33—C34	1.410 (6)
C5—H5A	0.9700	C33—H33	0.9300
C5—H5B	0.9700	C34—C35	1.394 (5)
C6—N2	1.495 (5)	C34—C36	1.505 (5)
C6—H6	0.9800	C35—O3	1.340 (5)
C7—N1	1.336 (5)	C36—H36A	0.9600
C7—C8	1.393 (6)	C36—H36B	0.9600
C7—H7	0.9300	C36—H36C	0.9600
C8—C13	1.387 (6)	C37—N4	1.339 (6)
C8—C9	1.392 (6)	C37—C38	1.427 (6)
C9—C10	1.395 (6)	C37—H37	0.9300
C9—H9	0.9300	C38—C43	1.388 (6)
C10—C11	1.398 (7)	C38—C39	1.403 (5)
C10—H10	0.9300	C39—C40	1.386 (6)
C11—C12	1.392 (7)	C39—H39	0.9300
C11—H11	0.9300	C40—C41	1.391 (6)
C12—C13	1.393 (6)	C40—H40	0.9300
C12—C14	1.526 (6)	C41—C42	1.399 (6)
C13—O1	1.326 (5)	C41—H41	0.9300
C14—H14A	0.9600	C42—C43	1.393 (6)
C14—H14B	0.9600	C42—C44	1.581 (6)
C14—H14C	0.9600	C43—O4	1.317 (5)
C15—N2	1.266 (5)	C44—H44A	0.9600
C15—C16	1.396 (6)	C44—H44B	0.9600
C15—H15	0.9300	C44—H44C	0.9600
C16—C21	1.397 (6)	C45—C50	1.377 (6)
C16—C17	1.402 (5)	C45—C46	1.405 (6)
C17—C18	1.374 (6)	C45—H45	0.9300
C17—H17	0.9300	C46—C47	1.379 (6)
C18—C19	1.386 (6)	C46—H46	0.9300
C18—H18	0.9300	C47—C48	1.392 (7)
C19—C20	1.380 (5)	C47—H47	0.9300
C19—H19	0.9300	C48—C49	1.373 (6)
C20—C21	1.385 (6)	C48—H48	0.9300
C20—C22	1.514 (6)	C49—C50	1.399 (6)
C21—O2	1.331 (5)	C49—H49	0.9300
C22—H22A	0.9600	C50—H50	0.9300
C22—H22B	0.9600	C51—C56	1.395 (7)
C22—H22C	0.9600	C51—C52	1.399 (6)
C23—N3	1.441 (5)	C51—H51	0.9300
C23—C24	1.542 (6)	C52—C53	1.398 (6)
C23—C28	1.549 (6)	C52—H52	0.9300
C23—H23	0.9800	C53—C54	1.381 (6)
C24—C25	1.552 (5)	C53—H53	0.9300
C24—H24A	0.9700	C54—C55	1.395 (6)
C24—H24B	0.9700	C54—H54	0.9300
C25—C26	1.549 (6)	C55—C56	1.385 (6)
C25—H25A	0.9700	C55—H55	0.9300
C25—H25B	0.9700	C56—H56	0.9300
C26—C27	1.526 (6)	O1—H1E	0.86 (5)
C26—H26A	0.9700	O2—H2E	0.87 (6)
C26—H26B	0.9700	O3—H3E	0.85 (5)
C27—C28	1.611 (5)	O4—H4E	0.88 (5)
N1—C1—C2	113.3 (4)	C25—C26—H26B	109.6
N1—C1—C6	109.7 (3)	H26A—C26—H26B	108.1
C2—C1—C6	106.8 (3)	C26—C27—C28	107.7 (3)
N1—C1—H1	109.0	C26—C27—H27A	110.2
C2—C1—H1	109.0	C28—C27—H27A	110.2
C6—C1—H1	109.0	C26—C27—H27B	110.2
C3—C2—C1	118.6 (4)	C28—C27—H27B	110.2
C3—C2—H2A	107.7	H27A—C27—H27B	108.5
C1—C2—H2A	107.7	N4—C28—C23	108.4 (3)
C3—C2—H2B	107.7	N4—C28—C27	109.4 (3)
C1—C2—H2B	107.7	C23—C28—C27	109.9 (3)
H2A—C2—H2B	107.1	N4—C28—H28	109.7
C2—C3—C4	109.3 (3)	C23—C28—H28	109.7
C2—C3—H3A	109.8	C27—C28—H28	109.7
C4—C3—H3A	109.8	N3—C29—C30	123.2 (4)
C2—C3—H3B	109.8	N3—C29—H29	118.4
C4—C3—H3B	109.8	C30—C29—H29	118.4
H3A—C3—H3B	108.3	C31—C30—C35	120.4 (4)
C5—C4—C3	115.6 (4)	C31—C30—C29	119.6 (4)
C5—C4—H4A	108.4	C35—C30—C29	120.0 (4)
C3—C4—H4A	108.4	C30—C31—C32	120.9 (4)
C5—C4—H4B	108.4	C30—C31—H31	119.6
C3—C4—H4B	108.4	C32—C31—H31	119.6
H4A—C4—H4B	107.4	C31—C32—C33	119.6 (4)
C6—C5—C4	107.6 (4)	C31—C32—H32	120.2
C6—C5—H5A	110.2	C33—C32—H32	120.2
C4—C5—H5A	110.2	C32—C33—C34	120.1 (4)
C6—C5—H5B	110.2	C32—C33—H33	119.9
C4—C5—H5B	110.2	C34—C33—H33	119.9
H5A—C5—H5B	108.5	C35—C34—C33	119.2 (4)
N2—C6—C5	107.6 (3)	C35—C34—C36	120.5 (4)
N2—C6—C1	105.4 (3)	C33—C34—C36	120.3 (4)
C5—C6—C1	114.4 (4)	O3—C35—C34	119.6 (4)
N2—C6—H6	109.8	O3—C35—C30	120.6 (4)
C5—C6—H6	109.8	C34—C35—C30	119.8 (4)
C1—C6—H6	109.8	C34—C36—H36A	109.5
N1—C7—C8	120.8 (4)	C34—C36—H36B	109.5
N1—C7—H7	119.6	H36A—C36—H36B	109.5
C8—C7—H7	119.6	C34—C36—H36C	109.5
C13—C8—C9	120.4 (4)	H36A—C36—H36C	109.5
C13—C8—C7	119.9 (4)	H36B—C36—H36C	109.5
C9—C8—C7	119.4 (4)	N4—C37—C38	119.7 (4)
C8—C9—C10	119.6 (4)	N4—C37—H37	120.2
C8—C9—H9	120.2	C38—C37—H37	120.2
C10—C9—H9	120.2	C43—C38—C39	120.4 (4)
C9—C10—C11	119.6 (4)	C43—C38—C37	121.3 (4)
C9—C10—H10	120.2	C39—C38—C37	118.3 (4)
C11—C10—H10	120.2	C40—C39—C38	119.0 (4)
C12—C11—C10	120.9 (4)	C40—C39—H39	120.5
C12—C11—H11	119.6	C38—C39—H39	120.5
C10—C11—H11	119.6	C39—C40—C41	121.8 (4)
C11—C12—C13	118.9 (4)	C39—C40—H40	119.1
C11—C12—C14	121.3 (4)	C41—C40—H40	119.1
C13—C12—C14	119.7 (4)	C40—C41—C42	118.3 (4)
O1—C13—C8	127.6 (4)	C40—C41—H41	120.9
O1—C13—C12	111.6 (4)	C42—C41—H41	120.9
C8—C13—C12	120.7 (4)	C43—C42—C41	121.1 (4)
C12—C14—H14A	109.5	C43—C42—C44	118.6 (4)
C12—C14—H14B	109.5	C41—C42—C44	120.3 (4)
H14A—C14—H14B	109.5	O4—C43—C38	118.2 (4)
C12—C14—H14C	109.5	O4—C43—C42	122.2 (4)
H14A—C14—H14C	109.5	C38—C43—C42	119.5 (4)
H14B—C14—H14C	109.5	C42—C44—H44A	109.5
N2—C15—C16	124.5 (4)	C42—C44—H44B	109.5
N2—C15—H15	117.7	H44A—C44—H44B	109.5
C16—C15—H15	117.7	C42—C44—H44C	109.5
C15—C16—C21	120.7 (4)	H44A—C44—H44C	109.5
C15—C16—C17	120.7 (4)	H44B—C44—H44C	109.5
C21—C16—C17	118.6 (4)	C50—C45—C46	120.0 (4)
C18—C17—C16	120.4 (4)	C50—C45—H45	120.0
C18—C17—H17	119.8	C46—C45—H45	120.0
C16—C17—H17	119.8	C47—C46—C45	119.9 (4)
C17—C18—C19	120.1 (4)	C47—C46—H46	120.0
C17—C18—H18	120.0	C45—C46—H46	120.0
C19—C18—H18	120.0	C46—C47—C48	119.5 (4)
C20—C19—C18	120.7 (4)	C46—C47—H47	120.3
C20—C19—H19	119.7	C48—C47—H47	120.3
C18—C19—H19	119.7	C49—C48—C47	121.1 (4)
C19—C20—C21	119.3 (4)	C49—C48—H48	119.5
C19—C20—C22	120.7 (4)	C47—C48—H48	119.5
C21—C20—C22	120.0 (4)	C48—C49—C50	119.5 (4)
O2—C21—C20	117.7 (4)	C48—C49—H49	120.2
O2—C21—C16	121.4 (4)	C50—C49—H49	120.2
C20—C21—C16	120.9 (4)	C45—C50—C49	120.0 (4)
C20—C22—H22A	109.5	C45—C50—H50	120.0
C20—C22—H22B	109.5	C49—C50—H50	120.0
H22A—C22—H22B	109.5	C56—C51—C52	119.5 (4)
C20—C22—H22C	109.5	C56—C51—H51	120.3
H22A—C22—H22C	109.5	C52—C51—H51	120.3
H22B—C22—H22C	109.5	C53—C52—C51	120.1 (5)
N3—C23—C24	109.6 (3)	C53—C52—H52	119.9
N3—C23—C28	109.1 (3)	C51—C52—H52	119.9
C24—C23—C28	113.1 (3)	C54—C53—C52	119.6 (4)
N3—C23—H23	108.3	C54—C53—H53	120.2
C24—C23—H23	108.3	C52—C53—H53	120.2
C28—C23—H23	108.3	C53—C54—C55	120.6 (4)
C23—C24—C25	109.6 (3)	C53—C54—H54	119.7
C23—C24—H24A	109.8	C55—C54—H54	119.7
C25—C24—H24A	109.8	C56—C55—C54	119.8 (4)
C23—C24—H24B	109.8	C56—C55—H55	120.1
C25—C24—H24B	109.8	C54—C55—H55	120.1
H24A—C24—H24B	108.2	C55—C56—C51	120.3 (4)
C26—C25—C24	109.5 (3)	C55—C56—H56	119.8
C26—C25—H25A	109.8	C51—C56—H56	119.8
C24—C25—H25A	109.8	C7—N1—C1	122.3 (4)
C26—C25—H25B	109.8	C15—N2—C6	121.1 (4)
C24—C25—H25B	109.8	C29—N3—C23	118.5 (3)
H25A—C25—H25B	108.2	C37—N4—C28	117.9 (4)
C27—C26—C25	110.3 (3)	C13—O1—H1E	108 (3)
C27—C26—H26A	109.6	C21—O2—H2E	109 (4)
C25—C26—H26A	109.6	C35—O3—H3E	108 (4)
C27—C26—H26B	109.6	C43—O4—H4E	113 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4E···N4	0.88 (5)	1.74 (5)	2.438 (5)	135 (4)
O3—H3E···N3	0.85 (5)	1.84 (5)	2.550 (4)	140 (5)
O2—H2E···N2	0.87 (6)	1.81 (6)	2.577 (5)	146 (5)
O1—H1E···N1	0.86 (5)	1.91 (5)	2.604 (4)	137 (4)