Intra­molecular hydrogen transfer in (S)-2-[(1-benzyl-2-hydroxy­ethyl­imino)meth­yl]-4-nitro­phenol, a new chiral Schiff base

The synthesis and crystal structure of the new title chiral Schiff base, C₁₆H₁₆N₂O₄, derived from the condensation of L-phenyl­alaninol [(S)-(-)-2-amino-3-phenyl-1-propanol] and 5-nitro­salicylaldehyde (2-hydr­oxy-5-nitro­benzaldehyde), are presented. There are two molecules in the asymmetric unit and they are stabilized in the solid state in the NH tautomeric form.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.108
• Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         90 PerFit

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.62
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3

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           26.06
           From the CIF: _reflns_number_total               3102
           Count of symmetry unique reflns         3107
           Completeness (_total/calc)             99.84%
           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

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

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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

(S)-2-[(1-benzyl-2-hydroxyethylimino)methyl]-4-nitrophenol

Crystal data

C16H16N2O4	F(000) = 632
Mr = 300.31	Dx = 1.364 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5910 reflections
a = 5.8623 (8) Å	θ = 2.6–25.4°
b = 8.1322 (10) Å	µ = 0.10 mm^−1
c = 30.674 (4) Å	T = 295 K
β = 91.450 (2)°	Block, orange
V = 1461.9 (3) Å^3	0.33 × 0.28 × 0.17 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3102 independent reflections
Radiation source: fine-focus sealed tube	2530 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 26.1°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.968, Tmax = 0.983	k = −10→10
15286 measured reflections	l = −37→37

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0619P)^2 + 0.0745P] where P = (Fo^2 + 2Fc^2)/3
3102 reflections	(Δ/σ)max = 0.005
407 parameters	Δρmax = 0.16 e Å^−3
1 restraint	Δρmin = −0.14 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
O5	0.0514 (3)	0.9170 (3)	0.68955 (7)	0.0682 (6)
C21	0.4332 (5)	0.6879 (3)	0.76162 (9)	0.0476 (6)
H21	0.5757	0.6378	0.7615	0.057*
C20	0.3046 (5)	0.6789 (3)	0.79777 (9)	0.0495 (6)
N4	0.4450 (4)	0.8581 (3)	0.65274 (7)	0.0529 (6)
C22	0.3522 (4)	0.7722 (3)	0.72463 (8)	0.0455 (6)
C17	0.1305 (4)	0.8474 (4)	0.72367 (9)	0.0507 (7)
C18	0.0071 (5)	0.8357 (4)	0.76324 (10)	0.0588 (7)
H18	−0.1358	0.8849	0.7646	0.071*
N3	0.3936 (5)	0.5900 (4)	0.83504 (7)	0.0641 (7)
C31	0.5463 (5)	0.8528 (4)	0.49793 (10)	0.0603 (8)
H31	0.4093	0.9105	0.4971	0.072*
C19	0.0918 (5)	0.7550 (4)	0.79890 (9)	0.0575 (8)
H19	0.0075	0.7505	0.8241	0.069*
C26	0.6196 (5)	0.7796 (4)	0.53630 (9)	0.0548 (7)
C23	0.4985 (5)	0.7837 (3)	0.68855 (8)	0.0488 (6)
H23	0.6414	0.7344	0.6910	0.059*
O8	0.7657 (4)	1.1251 (3)	0.64267 (8)	0.0757 (6)
H8	0.8688	1.0665	0.6524	0.114*
O7	0.2810 (5)	0.5851 (5)	0.86777 (7)	0.1011 (10)
O6	0.5793 (5)	0.5209 (4)	0.83292 (7)	0.0889 (8)
C24	0.5963 (5)	0.8688 (4)	0.61579 (8)	0.0532 (7)
H24	0.7364	0.8072	0.6226	0.064*
C30	0.6732 (6)	0.8418 (4)	0.46088 (9)	0.0664 (8)
H30	0.6202	0.8909	0.4352	0.080*
C27	0.8242 (5)	0.6938 (4)	0.53647 (10)	0.0627 (8)
H27	0.8758	0.6420	0.5619	0.075*
C25	0.4749 (5)	0.7899 (5)	0.57625 (9)	0.0676 (9)
H25A	0.4271	0.6798	0.5841	0.081*
H25B	0.3387	0.8530	0.5691	0.081*
C28	0.9520 (6)	0.6845 (5)	0.49946 (12)	0.0694 (9)
H28	1.0896	0.6276	0.5002	0.083*
C29	0.8771 (6)	0.7589 (4)	0.46151 (10)	0.0687 (9)
H29	0.9636	0.7531	0.4366	0.082*
C32	0.6568 (6)	1.0463 (4)	0.60716 (9)	0.0643 (8)
H32A	0.7559	1.0508	0.5823	0.077*
H32B	0.5183	1.1060	0.5994	0.077*
N2	1.0757 (4)	0.1642 (4)	0.85038 (7)	0.0570 (6)
C5	1.0232 (5)	0.3484 (4)	0.74284 (8)	0.0486 (6)
H5	0.8812	0.3976	0.7458	0.058*
C6	1.1195 (5)	0.2585 (3)	0.77740 (8)	0.0472 (6)
O1	1.4308 (3)	0.0996 (3)	0.80363 (7)	0.0704 (6)
N1	1.0349 (5)	0.4586 (3)	0.66934 (8)	0.0620 (6)
C4	1.1367 (5)	0.3646 (3)	0.70460 (8)	0.0502 (6)
C1	1.3402 (5)	0.1826 (4)	0.77287 (9)	0.0534 (7)
C7	1.0002 (5)	0.2455 (4)	0.81706 (9)	0.0528 (7)
H7	0.8603	0.2986	0.8190	0.063*
C2	1.4483 (5)	0.2052 (4)	0.73233 (10)	0.0592 (8)
H2	1.5906	0.1578	0.7284	0.071*
C8	0.9640 (5)	0.1523 (4)	0.89292 (8)	0.0560 (7)
H8A	1.0469	0.0708	0.9107	0.067*
O2	0.8404 (4)	0.5107 (3)	0.67306 (7)	0.0787 (7)
C10	0.8667 (5)	0.3199 (4)	0.96000 (8)	0.0549 (7)
C14	0.8619 (6)	0.2458 (5)	1.03549 (10)	0.0706 (9)
H14	0.9306	0.1934	1.0594	0.085*
O3	1.1463 (5)	0.4825 (4)	0.63664 (7)	0.0946 (8)
C11	0.6609 (5)	0.4003 (4)	0.96533 (10)	0.0627 (8)
H11	0.5917	0.4536	0.9416	0.075*
C12	0.5578 (5)	0.4028 (5)	1.00491 (11)	0.0700 (9)
H12	0.4195	0.4572	1.0078	0.084*
C3	1.3520 (5)	0.2931 (4)	0.69932 (9)	0.0576 (7)
H3	1.4280	0.3061	0.6733	0.069*
C13	0.6570 (6)	0.3257 (5)	1.04009 (10)	0.0704 (9)
H13	0.5867	0.3271	1.0669	0.084*
O4	0.6985 (5)	−0.0523 (3)	0.86423 (7)	0.0824 (7)
H4	0.6410	−0.0339	0.8401	0.124*
C15	0.9656 (6)	0.2431 (4)	0.99587 (11)	0.0631 (8)
H15	1.1042	0.1888	0.9932	0.076*
C16	0.7187 (5)	0.0961 (4)	0.88770 (9)	0.0657 (8)
H16A	0.6551	0.0814	0.9163	0.079*
H16B	0.6308	0.1807	0.8726	0.079*
C9	0.9802 (5)	0.3182 (4)	0.91641 (9)	0.0630 (8)
H9A	1.1399	0.3467	0.9207	0.076*
H9B	0.9103	0.4019	0.8979	0.076*
H1A	1.224 (6)	0.118 (5)	0.8444 (10)	0.077 (10)*
H1B	0.308 (5)	0.910 (4)	0.6516 (9)	0.067 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O5	0.0569 (12)	0.0763 (16)	0.0709 (13)	0.0051 (11)	−0.0091 (10)	0.0083 (12)
C21	0.0527 (15)	0.0406 (15)	0.0498 (15)	−0.0013 (13)	0.0061 (12)	0.0005 (12)
C20	0.0571 (16)	0.0433 (15)	0.0484 (15)	−0.0089 (13)	0.0060 (12)	0.0014 (12)
N4	0.0569 (14)	0.0561 (15)	0.0458 (13)	−0.0015 (12)	0.0063 (10)	0.0049 (11)
C22	0.0502 (15)	0.0402 (15)	0.0462 (14)	−0.0053 (12)	0.0049 (11)	−0.0026 (11)
C17	0.0480 (15)	0.0469 (16)	0.0571 (16)	−0.0075 (13)	−0.0028 (12)	−0.0016 (14)
C18	0.0407 (14)	0.0569 (18)	0.079 (2)	−0.0027 (14)	0.0077 (13)	−0.0092 (17)
N3	0.0830 (19)	0.0623 (17)	0.0473 (13)	−0.0117 (15)	0.0085 (13)	0.0072 (13)
C31	0.0635 (18)	0.0593 (19)	0.0579 (16)	0.0037 (16)	−0.0021 (14)	−0.0051 (15)
C19	0.0603 (17)	0.0585 (18)	0.0545 (17)	−0.0139 (15)	0.0187 (14)	−0.0066 (14)
C26	0.0563 (16)	0.0568 (19)	0.0515 (15)	−0.0117 (14)	0.0024 (12)	−0.0071 (13)
C23	0.0558 (15)	0.0457 (16)	0.0449 (15)	−0.0010 (13)	0.0014 (12)	0.0007 (12)
O8	0.0808 (16)	0.0607 (14)	0.0848 (15)	0.0020 (12)	−0.0122 (12)	−0.0153 (13)
O7	0.114 (2)	0.134 (3)	0.0567 (13)	−0.010 (2)	0.0251 (13)	0.0240 (16)
O6	0.1046 (19)	0.0932 (19)	0.0691 (14)	0.0266 (17)	0.0054 (13)	0.0257 (14)
C24	0.0592 (16)	0.0589 (18)	0.0417 (13)	−0.0059 (14)	0.0074 (12)	0.0050 (13)
C30	0.093 (2)	0.059 (2)	0.0467 (15)	−0.0004 (19)	0.0002 (15)	−0.0009 (15)
C27	0.0692 (19)	0.064 (2)	0.0548 (16)	−0.0044 (17)	−0.0055 (14)	0.0027 (15)
C25	0.0664 (18)	0.080 (2)	0.0570 (17)	−0.0210 (18)	0.0079 (14)	−0.0104 (16)
C28	0.063 (2)	0.067 (2)	0.0774 (19)	0.0078 (17)	0.0067 (16)	−0.0069 (18)
C29	0.082 (2)	0.062 (2)	0.0628 (19)	0.0013 (18)	0.0174 (16)	−0.0097 (16)
C32	0.076 (2)	0.063 (2)	0.0541 (16)	−0.0113 (16)	−0.0007 (14)	0.0074 (15)
N2	0.0610 (15)	0.0632 (16)	0.0468 (13)	0.0008 (13)	0.0031 (11)	0.0007 (12)
C5	0.0501 (15)	0.0430 (15)	0.0532 (15)	−0.0038 (13)	0.0098 (12)	−0.0055 (13)
C6	0.0531 (15)	0.0447 (15)	0.0441 (14)	−0.0067 (13)	0.0070 (12)	−0.0032 (12)
O1	0.0622 (12)	0.0818 (16)	0.0668 (12)	0.0090 (12)	−0.0079 (10)	−0.0036 (13)
N1	0.0816 (18)	0.0511 (15)	0.0538 (14)	−0.0023 (15)	0.0122 (13)	0.0019 (12)
C4	0.0596 (16)	0.0428 (15)	0.0486 (15)	−0.0079 (13)	0.0102 (12)	−0.0055 (12)
C1	0.0534 (16)	0.0479 (16)	0.0586 (17)	−0.0063 (14)	−0.0047 (13)	−0.0118 (14)
C7	0.0558 (16)	0.0498 (16)	0.0530 (16)	−0.0002 (13)	0.0059 (12)	−0.0032 (13)
C2	0.0459 (15)	0.062 (2)	0.070 (2)	−0.0061 (14)	0.0130 (14)	−0.0172 (16)
C8	0.0681 (18)	0.0597 (18)	0.0402 (14)	0.0001 (15)	0.0011 (12)	0.0065 (13)
O2	0.0958 (17)	0.0692 (15)	0.0716 (14)	0.0243 (14)	0.0126 (12)	0.0130 (12)
C10	0.0614 (17)	0.0555 (17)	0.0479 (15)	−0.0097 (15)	0.0013 (12)	−0.0013 (13)
C14	0.098 (3)	0.067 (2)	0.0461 (16)	0.004 (2)	0.0018 (16)	0.0040 (15)
O3	0.1143 (19)	0.115 (2)	0.0562 (12)	−0.0013 (19)	0.0304 (12)	0.0214 (15)
C11	0.0688 (19)	0.0627 (19)	0.0562 (16)	0.0023 (16)	−0.0087 (14)	0.0008 (14)
C12	0.065 (2)	0.071 (2)	0.074 (2)	0.0040 (17)	0.0083 (16)	−0.0076 (18)
C3	0.0620 (17)	0.0557 (18)	0.0560 (17)	−0.0094 (15)	0.0180 (14)	−0.0096 (15)
C13	0.087 (2)	0.065 (2)	0.0597 (18)	−0.0014 (19)	0.0214 (16)	−0.0076 (17)
O4	0.1115 (19)	0.0591 (14)	0.0757 (14)	−0.0156 (14)	−0.0140 (13)	−0.0012 (12)
C15	0.0661 (19)	0.066 (2)	0.0575 (17)	0.0033 (16)	0.0026 (14)	0.0009 (16)
C16	0.082 (2)	0.066 (2)	0.0487 (15)	−0.0183 (17)	0.0084 (14)	−0.0004 (15)
C9	0.0745 (19)	0.067 (2)	0.0480 (15)	−0.0151 (17)	0.0062 (13)	0.0003 (15)

Geometric parameters (Å, º)

O5—C17	1.267 (3)	N2—C7	1.287 (4)
C21—C20	1.358 (4)	N2—C8	1.478 (3)
C21—C22	1.398 (4)	N2—H1A	0.97 (3)
C21—H21	0.9300	C5—C4	1.370 (3)
C20—C19	1.394 (4)	C5—C6	1.395 (4)
C20—N3	1.439 (4)	C5—H5	0.9300
N4—C23	1.286 (3)	C6—C7	1.422 (4)
N4—C24	1.460 (3)	C6—C1	1.444 (4)
N4—H1B	0.91 (3)	O1—C1	1.266 (3)
C22—C23	1.420 (3)	N1—O2	1.224 (3)
C22—C17	1.436 (4)	N1—O3	1.226 (3)
C17—C18	1.432 (4)	N1—C4	1.442 (4)
C18—C19	1.359 (4)	C4—C3	1.403 (4)
C18—H18	0.9300	C1—C2	1.422 (4)
N3—O7	1.216 (3)	C7—H7	0.9300
N3—O6	1.228 (4)	C2—C3	1.351 (4)
C31—C30	1.377 (4)	C2—H2	0.9300
C31—C26	1.378 (4)	C8—C16	1.514 (4)
C31—H31	0.9300	C8—C9	1.531 (4)
C19—H19	0.9300	C8—H8A	0.9800
C26—C27	1.387 (4)	C10—C15	1.380 (4)
C26—C25	1.510 (4)	C10—C11	1.386 (4)
C23—H23	0.9300	C10—C9	1.509 (4)
O8—C32	1.404 (3)	C14—C15	1.373 (5)
O8—H8	0.8200	C14—C13	1.376 (5)
C24—C32	1.511 (5)	C14—H14	0.9300
C24—C25	1.531 (4)	C11—C12	1.370 (4)
C24—H24	0.9800	C11—H11	0.9300
C30—C29	1.372 (5)	C12—C13	1.366 (5)
C30—H30	0.9300	C12—H12	0.9300
C27—C28	1.378 (5)	C3—H3	0.9300
C27—H27	0.9300	C13—H13	0.9300
C25—H25A	0.9700	O4—C16	1.408 (4)
C25—H25B	0.9700	O4—H4	0.8200
C28—C29	1.374 (5)	C15—H15	0.9300
C28—H28	0.9300	C16—H16A	0.9700
C29—H29	0.9300	C16—H16B	0.9700
C32—H32A	0.9700	C9—H9A	0.9700
C32—H32B	0.9700	C9—H9B	0.9700
C20—C21—C22	120.3 (3)	C7—N2—C8	125.7 (3)
C20—C21—H21	119.8	C7—N2—H1A	110.0 (19)
C22—C21—H21	119.8	C8—N2—H1A	124.2 (19)
C21—C20—C19	120.8 (3)	C4—C5—C6	120.3 (3)
C21—C20—N3	118.6 (3)	C4—C5—H5	119.8
C19—C20—N3	120.7 (2)	C6—C5—H5	119.8
C23—N4—C24	123.5 (3)	C5—C6—C7	119.4 (3)
C23—N4—H1B	116.6 (19)	C5—C6—C1	119.8 (2)
C24—N4—H1B	119.9 (19)	C7—C6—C1	120.8 (3)
C21—C22—C23	117.7 (2)	O2—N1—O3	122.5 (3)
C21—C22—C17	120.9 (2)	O2—N1—C4	118.9 (2)
C23—C22—C17	121.3 (2)	O3—N1—C4	118.6 (3)
O5—C17—C18	123.2 (3)	C5—C4—C3	121.1 (3)
O5—C17—C22	121.3 (2)	C5—C4—N1	119.5 (3)
C18—C17—C22	115.5 (3)	C3—C4—N1	119.3 (2)
C19—C18—C17	122.2 (3)	O1—C1—C2	122.2 (3)
C19—C18—H18	118.9	O1—C1—C6	121.1 (3)
C17—C18—H18	118.9	C2—C1—C6	116.7 (3)
O7—N3—O6	122.0 (3)	N2—C7—C6	123.4 (3)
O7—N3—C20	118.6 (3)	N2—C7—H7	118.3
O6—N3—C20	119.5 (2)	C6—C7—H7	118.3
C30—C31—C26	120.9 (3)	C3—C2—C1	122.5 (3)
C30—C31—H31	119.6	C3—C2—H2	118.8
C26—C31—H31	119.6	C1—C2—H2	118.8
C18—C19—C20	120.2 (3)	N2—C8—C16	111.5 (2)
C18—C19—H19	119.9	N2—C8—C9	109.5 (2)
C20—C19—H19	119.9	C16—C8—C9	111.3 (3)
C31—C26—C27	118.1 (3)	N2—C8—H8A	108.1
C31—C26—C25	120.0 (3)	C16—C8—H8A	108.1
C27—C26—C25	121.9 (3)	C9—C8—H8A	108.1
N4—C23—C22	123.9 (3)	C15—C10—C11	118.0 (3)
N4—C23—H23	118.1	C15—C10—C9	121.1 (3)
C22—C23—H23	118.1	C11—C10—C9	120.9 (3)
C32—O8—H8	109.5	C15—C14—C13	120.4 (3)
N4—C24—C32	110.1 (3)	C15—C14—H14	119.8
N4—C24—C25	108.1 (2)	C13—C14—H14	119.8
C32—C24—C25	111.6 (2)	C12—C11—C10	121.1 (3)
N4—C24—H24	109.0	C12—C11—H11	119.4
C32—C24—H24	109.0	C10—C11—H11	119.4
C25—C24—H24	109.0	C13—C12—C11	120.3 (3)
C29—C30—C31	120.6 (3)	C13—C12—H12	119.8
C29—C30—H30	119.7	C11—C12—H12	119.8
C31—C30—H30	119.7	C2—C3—C4	119.5 (3)
C28—C27—C26	120.8 (3)	C2—C3—H3	120.2
C28—C27—H27	119.6	C4—C3—H3	120.2
C26—C27—H27	119.6	C12—C13—C14	119.4 (3)
C26—C25—C24	114.0 (2)	C12—C13—H13	120.3
C26—C25—H25A	108.8	C14—C13—H13	120.3
C24—C25—H25A	108.8	C16—O4—H4	109.5
C26—C25—H25B	108.8	C14—C15—C10	120.8 (3)
C24—C25—H25B	108.8	C14—C15—H15	119.6
H25A—C25—H25B	107.6	C10—C15—H15	119.6
C29—C28—C27	120.3 (3)	O4—C16—C8	112.4 (3)
C29—C28—H28	119.8	O4—C16—H16A	109.1
C27—C28—H28	119.8	C8—C16—H16A	109.1
C30—C29—C28	119.2 (3)	O4—C16—H16B	109.1
C30—C29—H29	120.4	C8—C16—H16B	109.1
C28—C29—H29	120.4	H16A—C16—H16B	107.9
O8—C32—C24	113.9 (2)	C10—C9—C8	113.7 (3)
O8—C32—H32A	108.8	C10—C9—H9A	108.8
C24—C32—H32A	108.8	C8—C9—H9A	108.8
O8—C32—H32B	108.8	C10—C9—H9B	108.8
C24—C32—H32B	108.8	C8—C9—H9B	108.8
H32A—C32—H32B	107.7	H9A—C9—H9B	107.7
C22—C21—C20—C19	−0.9 (4)	C4—C5—C6—C7	179.0 (3)
C22—C21—C20—N3	179.6 (2)	C4—C5—C6—C1	0.2 (4)
C20—C21—C22—C23	177.3 (2)	C6—C5—C4—C3	−0.6 (4)
C20—C21—C22—C17	−1.5 (4)	C6—C5—C4—N1	−179.7 (2)
C21—C22—C17—O5	−176.5 (3)	O2—N1—C4—C5	−6.0 (4)
C23—C22—C17—O5	4.8 (4)	O3—N1—C4—C5	174.4 (3)
C21—C22—C17—C18	2.6 (4)	O2—N1—C4—C3	174.9 (3)
C23—C22—C17—C18	−176.0 (3)	O3—N1—C4—C3	−4.7 (4)
O5—C17—C18—C19	177.4 (3)	C5—C6—C1—O1	−179.6 (3)
C22—C17—C18—C19	−1.7 (4)	C7—C6—C1—O1	1.6 (4)
C21—C20—N3—O7	178.3 (3)	C5—C6—C1—C2	0.1 (4)
C19—C20—N3—O7	−1.3 (5)	C7—C6—C1—C2	−178.7 (3)
C21—C20—N3—O6	−2.1 (4)	C8—N2—C7—C6	177.3 (3)
C19—C20—N3—O6	178.4 (3)	C5—C6—C7—N2	179.5 (3)
C17—C18—C19—C20	−0.5 (5)	C1—C6—C7—N2	−1.7 (4)
C21—C20—C19—C18	1.8 (4)	O1—C1—C2—C3	179.7 (3)
N3—C20—C19—C18	−178.6 (3)	C6—C1—C2—C3	0.0 (4)
C30—C31—C26—C27	−0.3 (5)	C7—N2—C8—C16	53.4 (4)
C30—C31—C26—C25	−178.6 (3)	C7—N2—C8—C9	−70.3 (4)
C24—N4—C23—C22	−179.8 (3)	C15—C10—C11—C12	−0.4 (5)
C21—C22—C23—N4	−179.8 (3)	C9—C10—C11—C12	−179.7 (3)
C17—C22—C23—N4	−1.1 (4)	C10—C11—C12—C13	0.1 (5)
C23—N4—C24—C32	−117.1 (3)	C1—C2—C3—C4	−0.4 (5)
C23—N4—C24—C25	120.8 (3)	C5—C4—C3—C2	0.7 (4)
C26—C31—C30—C29	−0.7 (5)	N1—C4—C3—C2	179.8 (3)
C31—C26—C27—C28	1.0 (5)	C11—C12—C13—C14	0.2 (6)
C25—C26—C27—C28	179.2 (3)	C15—C14—C13—C12	−0.2 (6)
C31—C26—C25—C24	−122.1 (3)	C13—C14—C15—C10	−0.1 (6)
C27—C26—C25—C24	59.7 (4)	C11—C10—C15—C14	0.3 (5)
N4—C24—C25—C26	−175.2 (3)	C9—C10—C15—C14	179.7 (3)
C32—C24—C25—C26	63.6 (4)	N2—C8—C16—O4	54.3 (3)
C26—C27—C28—C29	−0.7 (5)	C9—C8—C16—O4	177.0 (2)
C31—C30—C29—C28	1.0 (5)	C15—C10—C9—C8	74.4 (4)
C27—C28—C29—C30	−0.3 (5)	C11—C10—C9—C8	−106.4 (3)
N4—C24—C32—O8	59.1 (4)	N2—C8—C9—C10	178.9 (2)
C25—C24—C32—O8	179.1 (2)	C16—C8—C9—C10	55.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1A···O1	0.97 (3)	1.77 (3)	2.610 (3)	143 (3)
N4—H1B···O5	0.91 (3)	1.92 (3)	2.638 (3)	134 (3)