Ethyl 2-{[(1Z)-(3-methyl-5-oxo-1-phenyl-1,5-di­hydro­pyrazol-4-yl­idene)(phenyl)­methyl]­amino}-3-phenyl­propanoate

In the title compound, C₂₈H₂₇N₃O₃, the pyrazolone ring and the N atom of the 2-amino-3-phenyl­propanoate group are essentially coplanar. The compound is in an en­amine–keto form and its structure is stabilized by one strong intramolec­ular N—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.051
• wR factor = 0.130
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C16
PLAT391_ALERT_3_B Deviating Methyl C4      H-C-H Bond Angle ......      99.69 Deg.

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.79 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.39 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.
PLAT741_ALERT_1_C Bond    Calc    1.391(3), Rep     1.39100 ......    Missing su
              C17  -C18     1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      20.40 Deg.
              C151 -O3   -C15     1.555   1.555   1.555

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

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

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Ethyl 2-{[(1Z)-(3-methyl-5-oxo-1-phenyl-1,5-dihydropyrazol-4- ylidene)(phenyl)methyl]amino}-3-phenylpropanoate

Crystal data

C28H27N3O3	F(000) = 960
Mr = 453.53	Dx = 1.268 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4184 reflections
a = 10.521 (3) Å	θ = 1.9–26.4°
b = 16.629 (5) Å	µ = 0.08 mm^−1
c = 14.080 (4) Å	T = 293 K
β = 105.315 (5)°	Block, yellow
V = 2375.9 (12) Å^3	0.32 × 0.24 × 0.22 mm
Z = 4

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	2661 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
φ and ω scans	h = −12→12
12125 measured reflections	k = −19→19
4184 independent reflections	l = −15→16

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) = 0.130	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0536P)^2 + 0.8249P] where P = (Fo^2 + 2Fc^2)/3
4184 reflections	(Δ/σ)max = 0.015
321 parameters	Δρmax = 0.24 e Å^−3
1 restraint	Δρmin = −0.31 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	Occ. (<1)
N1	0.21200 (17)	0.15615 (12)	1.05366 (13)	0.0387 (5)
N2	0.33706 (18)	0.19039 (13)	1.09189 (13)	0.0453 (5)
N3	0.26208 (19)	0.07896 (12)	0.78347 (13)	0.0437 (5)
H3	0.1850	0.0738	0.7942	0.044 (7)*
O1	0.09632 (15)	0.09465 (11)	0.90596 (12)	0.0477 (5)
O2	0.37415 (19)	−0.07743 (13)	0.77333 (15)	0.0709 (6)
O3	0.45465 (18)	−0.02602 (11)	0.65441 (13)	0.0609 (5)
C1	0.1979 (2)	0.12586 (14)	0.96010 (16)	0.0361 (5)
C2	0.3247 (2)	0.13781 (14)	0.94113 (15)	0.0355 (5)
C3	0.4033 (2)	0.17905 (15)	1.02618 (16)	0.0412 (6)
C4	0.5405 (3)	0.2099 (2)	1.0467 (2)	0.0617 (8)
H41	0.5555	0.2404	0.9919	0.078*
H42	0.5586	0.2459	1.1005	0.086*
H43	0.6038	0.1700	1.0516	0.098*
C5	0.3553 (2)	0.11119 (14)	0.85624 (16)	0.0358 (5)
C6	0.2828 (2)	0.04536 (15)	0.69242 (17)	0.0436 (6)
H6	0.3209	0.0886	0.6541	0.049*
C7	0.1529 (2)	0.01398 (16)	0.62672 (19)	0.0511 (7)
H71	0.1807	−0.0079	0.5686	0.060*
H72	0.1224	−0.0313	0.6675	0.081*
C8	0.0468 (2)	0.07688 (15)	0.59175 (17)	0.0438 (6)
C9	−0.0639 (3)	0.07700 (18)	0.62575 (19)	0.0567 (7)
H9	−0.0677	0.0380	0.6773	0.060*
C10	−0.1639 (3)	0.1319 (2)	0.5901 (2)	0.0682 (9)
H10	−0.2403	0.1296	0.6147	0.086*
C11	−0.1534 (3)	0.18765 (19)	0.5212 (2)	0.0628 (8)
H11	−0.2271	0.2278	0.4960	0.073*
C12	−0.0437 (3)	0.18888 (17)	0.48694 (19)	0.0559 (7)
H12	−0.0339	0.2280	0.4415	0.065*
C13	0.0565 (3)	0.13388 (17)	0.52144 (18)	0.0506 (7)
H13	0.1333	0.1353	0.4972	0.052*
C14	0.3761 (2)	−0.02639 (17)	0.71382 (18)	0.0475 (6)
C15	0.5255 (6)	−0.1040 (4)	0.6516 (5)	0.0556 (19)*	0.50
H150	0.4722	−0.1416	0.6052	0.067*	0.50
H151	0.5535	−0.1288	0.7161	0.067*	0.50
C16	0.6452 (7)	−0.0721 (5)	0.6159 (6)	0.099 (2)*	0.50
H16A	0.7159	−0.1104	0.6325	0.149*	0.50
H16B	0.6745	−0.0217	0.6474	0.149*	0.50
H16C	0.6187	−0.0646	0.5458	0.149*	0.50
C151	0.5612 (7)	−0.0855 (4)	0.6747 (5)	0.060 (2)*	0.50
H152	0.5306	−0.1363	0.6943	0.072*	0.50
H153	0.6349	−0.0668	0.7271	0.072*	0.50
C161	0.60236 (16)	−0.09546 (11)	0.57947 (12)	0.0726 (19)*	0.50
H164	0.6503	−0.1449	0.5817	0.109*	0.50
H165	0.6574	−0.0512	0.5720	0.109*	0.50
H166	0.5254	−0.0966	0.5247	0.109*	0.50
C17	0.49251 (16)	0.11539 (11)	0.84526 (12)	0.0371 (6)
C18	0.58424 (16)	0.05823 (11)	0.89219 (12)	0.0522 (7)
H18	0.5519	0.0119	0.9308	0.068*
C19	0.7129 (3)	0.06343 (18)	0.8871 (2)	0.0610 (8)
H19	0.7748	0.0196	0.9188	0.074*
C20	0.7532 (3)	0.12559 (19)	0.83800 (19)	0.0587 (8)
H20	0.8396	0.1316	0.8342	0.058*
C21	0.6629 (2)	0.18228 (18)	0.79178 (19)	0.0560 (7)
H21	0.6879	0.2279	0.7611	0.077*
C22	0.5325 (2)	0.17726 (15)	0.79387 (17)	0.0452 (6)
H22	0.4664	0.2174	0.7637	0.052*
C23	0.1208 (2)	0.15830 (14)	1.11201 (16)	0.0362 (5)
C24	0.1409 (2)	0.21183 (15)	1.19036 (17)	0.0463 (6)
H24	0.2262	0.2453	1.2069	0.053*
C25	0.0505 (3)	0.21549 (17)	1.24569 (19)	0.0544 (7)
H25	0.0710	0.2530	1.3033	0.077*
C26	−0.0586 (3)	0.16633 (16)	1.22501 (19)	0.0532 (7)
H26	−0.1270	0.1671	1.2655	0.060*
C27	−0.0772 (3)	0.11233 (16)	1.14806 (19)	0.0505 (7)
H27	−0.1623	0.0758	1.1284	0.062*
C28	0.0122 (2)	0.10787 (15)	1.09169 (18)	0.0455 (6)
H28	0.0011	0.0694	1.0390	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0330 (11)	0.0481 (12)	0.0361 (11)	−0.0071 (9)	0.0113 (9)	−0.0076 (9)
N2	0.0356 (11)	0.0634 (14)	0.0366 (11)	−0.0137 (10)	0.0090 (9)	−0.0086 (10)
N3	0.0316 (11)	0.0626 (14)	0.0370 (11)	0.0015 (10)	0.0090 (9)	−0.0112 (10)
O1	0.0332 (9)	0.0657 (12)	0.0444 (10)	−0.0108 (8)	0.0104 (8)	−0.0167 (8)
O2	0.0688 (14)	0.0738 (14)	0.0755 (14)	0.0147 (11)	0.0286 (11)	0.0245 (12)
O3	0.0631 (12)	0.0676 (13)	0.0596 (12)	0.0267 (10)	0.0298 (10)	0.0091 (10)
C1	0.0339 (13)	0.0398 (14)	0.0346 (13)	−0.0004 (11)	0.0087 (11)	−0.0015 (11)
C2	0.0315 (12)	0.0435 (14)	0.0312 (12)	−0.0006 (11)	0.0079 (10)	0.0020 (10)
C3	0.0352 (13)	0.0529 (16)	0.0347 (13)	−0.0074 (11)	0.0079 (11)	0.0011 (11)
C4	0.0444 (16)	0.098 (2)	0.0443 (16)	−0.0240 (18)	0.0147 (13)	−0.0156 (17)
C5	0.0321 (12)	0.0404 (14)	0.0326 (12)	0.0011 (10)	0.0046 (10)	0.0037 (10)
C6	0.0419 (14)	0.0521 (16)	0.0359 (13)	0.0068 (12)	0.0085 (11)	−0.0058 (12)
C7	0.0496 (16)	0.0541 (17)	0.0440 (15)	0.0049 (13)	0.0025 (12)	−0.0121 (13)
C8	0.0447 (15)	0.0478 (15)	0.0336 (13)	0.0010 (12)	0.0011 (11)	−0.0131 (12)
C9	0.0603 (18)	0.068 (2)	0.0427 (15)	−0.0005 (15)	0.0159 (14)	−0.0036 (14)
C10	0.0510 (18)	0.095 (3)	0.064 (2)	0.0102 (17)	0.0240 (16)	−0.0102 (18)
C11	0.0570 (18)	0.075 (2)	0.0527 (17)	0.0231 (16)	0.0087 (15)	−0.0050 (16)
C12	0.0641 (19)	0.0552 (18)	0.0447 (16)	0.0082 (15)	0.0076 (14)	−0.0029 (14)
C13	0.0434 (15)	0.0631 (18)	0.0465 (15)	0.0008 (13)	0.0139 (13)	−0.0108 (14)
C14	0.0434 (15)	0.0591 (18)	0.0394 (14)	0.0050 (13)	0.0097 (12)	−0.0018 (13)
C17	0.0330 (13)	0.0483 (15)	0.0295 (12)	0.0010 (11)	0.0073 (10)	0.0000 (11)
C18	0.0398 (15)	0.0598 (18)	0.0556 (16)	0.0039 (13)	0.0099 (13)	0.0132 (14)
C19	0.0413 (16)	0.066 (2)	0.073 (2)	0.0138 (14)	0.0103 (15)	0.0073 (16)
C20	0.0329 (15)	0.092 (2)	0.0522 (17)	−0.0031 (15)	0.0132 (13)	−0.0021 (16)
C21	0.0435 (16)	0.077 (2)	0.0481 (16)	−0.0112 (15)	0.0133 (13)	0.0113 (15)
C22	0.0403 (14)	0.0530 (16)	0.0404 (14)	0.0023 (12)	0.0073 (11)	0.0072 (12)
C23	0.0359 (13)	0.0390 (14)	0.0353 (13)	0.0024 (11)	0.0120 (10)	0.0025 (10)
C24	0.0470 (15)	0.0527 (16)	0.0422 (14)	−0.0065 (13)	0.0172 (12)	−0.0065 (12)
C25	0.0631 (18)	0.0578 (18)	0.0475 (16)	−0.0039 (15)	0.0237 (14)	−0.0106 (13)
C26	0.0565 (17)	0.0606 (18)	0.0517 (16)	0.0031 (14)	0.0306 (14)	−0.0005 (14)
C27	0.0471 (15)	0.0528 (17)	0.0569 (17)	−0.0062 (13)	0.0229 (13)	0.0001 (13)
C28	0.0471 (15)	0.0424 (15)	0.0514 (15)	−0.0053 (12)	0.0209 (13)	−0.0089 (12)

Geometric parameters (Å, º)

N1—C1	1.381 (3)	C13—H13	0.96
N1—N2	1.404 (2)	C15—C16	1.567 (7)
N1—C23	1.419 (3)	C15—H150	0.97
N2—C3	1.311 (3)	C15—H151	0.97
N3—C5	1.330 (3)	C16—H16A	0.96
N3—C6	1.466 (3)	C16—H16B	0.96
N3—H3	0.87	C16—H16C	0.96
O1—C1	1.250 (3)	C151—C161	1.523 (7)
O2—C14	1.197 (3)	C151—H152	0.97
O3—C14	1.322 (3)	C151—H153	0.97
O3—C151	1.465 (7)	C161—H164	0.96
O3—C15	1.501 (7)	C161—H165	0.96
C1—C2	1.442 (3)	C161—H166	0.96
C2—C5	1.389 (3)	C17—C22	1.385 (3)
C2—C3	1.437 (3)	C17—C18	1.391
C3—C4	1.486 (3)	C18—C19	1.377 (3)
C4—H41	0.97	C18—H18	1.05
C4—H42	0.94	C19—C20	1.371 (4)
C4—H43	0.93	C19—H19	1.00
C5—C17	1.494 (3)	C20—C21	1.374 (4)
C6—C14	1.524 (3)	C20—H20	0.93
C6—C7	1.525 (3)	C21—C22	1.382 (3)
C6—H6	1.04	C21—H21	0.94
C7—C8	1.514 (3)	C22—H22	0.98
C7—H71	1.01	C23—C28	1.385 (3)
C7—H72	1.05	C23—C24	1.390 (3)
C8—C9	1.371 (4)	C24—C25	1.381 (3)
C8—C13	1.394 (4)	C24—H24	1.03
C9—C10	1.383 (4)	C25—C26	1.376 (4)
C9—H9	0.98	C25—H25	1.00
C10—C11	1.368 (4)	C26—C27	1.381 (3)
C10—H10	0.96	C26—H26	1.03
C11—C12	1.364 (4)	C27—C28	1.383 (3)
C11—H11	1.01	C27—H27	1.06
C12—C13	1.383 (4)	C28—H28	0.96
C12—H12	0.94
C1—N1—N2	111.53 (17)	O3—C15—C16	99.4 (5)
C1—N1—C23	130.01 (18)	O3—C15—H150	111.9
N2—N1—C23	118.46 (17)	C16—C15—H150	111.9
C3—N2—N1	106.89 (17)	O3—C15—H151	111.9
C5—N3—C6	125.3 (2)	C16—C15—H151	111.9
C5—N3—H3	116.0	H150—C15—H151	109.6
C6—N3—H3	118.4	C15—C16—H16A	109.5
C14—O3—C151	116.6 (3)	C15—C16—H16B	109.5
C14—O3—C15	114.2 (3)	H16A—C16—H16B	109.5
C151—O3—C15	20.4 (4)	C15—C16—H16C	109.5
O1—C1—N1	126.3 (2)	H16A—C16—H16C	109.5
O1—C1—C2	128.9 (2)	H16B—C16—H16C	109.5
N1—C1—C2	104.79 (18)	O3—C151—C161	106.5 (4)
C5—C2—C3	131.0 (2)	O3—C151—H152	110.4
C5—C2—C1	123.4 (2)	C161—C151—H152	110.4
C3—C2—C1	105.57 (19)	O3—C151—H153	110.4
N2—C3—C2	111.1 (2)	C161—C151—H153	110.4
N2—C3—C4	118.9 (2)	H152—C151—H153	108.6
C2—C3—C4	130.0 (2)	C151—C161—H164	109.5
C3—C4—H41	112.2	C151—C161—H165	109.5
C3—C4—H42	110.8	H164—C161—H165	109.5
H41—C4—H42	105.4	C151—C161—H166	109.5
C3—C4—H43	114.0	H164—C161—H166	109.5
H41—C4—H43	99.7	H165—C161—H166	109.5
H42—C4—H43	113.8	C22—C17—C18	119.17 (12)
N3—C5—C2	120.0 (2)	C22—C17—C5	121.58 (18)
N3—C5—C17	118.38 (19)	C18—C17—C5	119.16 (11)
C2—C5—C17	121.57 (19)	C19—C18—C17	120.04 (15)
N3—C6—C14	111.23 (19)	C19—C18—H18	122.0
N3—C6—C7	110.2 (2)	C17—C18—H18	117.9
C14—C6—C7	106.2 (2)	C20—C19—C18	120.8 (2)
N3—C6—H6	110.9	C20—C19—H19	121.5
C14—C6—H6	109.1	C18—C19—H19	117.6
C7—C6—H6	109.1	C19—C20—C21	119.3 (3)
C8—C7—C6	115.2 (2)	C19—C20—H20	123.1
C8—C7—H71	109.4	C21—C20—H20	117.6
C6—C7—H71	102.2	C20—C21—C22	121.0 (3)
C8—C7—H72	111.6	C20—C21—H21	121.8
C6—C7—H72	105.6	C22—C21—H21	117.2
H71—C7—H72	112.4	C21—C22—C17	119.7 (2)
C9—C8—C13	118.4 (2)	C21—C22—H22	123.1
C9—C8—C7	120.6 (3)	C17—C22—H22	117.1
C13—C8—C7	121.0 (2)	C28—C23—C24	119.7 (2)
C8—C9—C10	120.6 (3)	C28—C23—N1	120.8 (2)
C8—C9—H9	117.5	C24—C23—N1	119.4 (2)
C10—C9—H9	121.9	C25—C24—C23	119.5 (2)
C11—C10—C9	120.6 (3)	C25—C24—H24	122.5
C11—C10—H10	121.1	C23—C24—H24	117.9
C9—C10—H10	118.4	C26—C25—C24	121.0 (2)
C12—C11—C10	119.7 (3)	C26—C25—H25	122.1
C12—C11—H11	120.5	C24—C25—H25	116.8
C10—C11—H11	119.8	C25—C26—C27	119.3 (2)
C11—C12—C13	120.3 (3)	C25—C26—H26	122.8
C11—C12—H12	120.5	C27—C26—H26	117.9
C13—C12—H12	119.2	C26—C27—C28	120.6 (2)
C12—C13—C8	120.5 (3)	C26—C27—H27	120.9
C12—C13—H13	119.7	C28—C27—H27	118.4
C8—C13—H13	119.8	C27—C28—C23	119.8 (2)
O2—C14—O3	125.1 (2)	C27—C28—H28	121.1
O2—C14—C6	124.4 (2)	C23—C28—H28	119.1
O3—C14—C6	110.4 (2)
C1—N1—N2—C3	−2.7 (3)	C151—O3—C14—O2	−10.6 (5)
C23—N1—N2—C3	178.4 (2)	C15—O3—C14—O2	11.9 (5)
N2—N1—C1—O1	−177.1 (2)	C151—O3—C14—C6	172.4 (4)
C23—N1—C1—O1	1.6 (4)	C15—O3—C14—C6	−165.2 (3)
N2—N1—C1—C2	3.4 (3)	N3—C6—C14—O2	41.1 (4)
C23—N1—C1—C2	−177.8 (2)	C7—C6—C14—O2	−78.8 (3)
O1—C1—C2—C5	−3.3 (4)	N3—C6—C14—O3	−141.8 (2)
N1—C1—C2—C5	176.2 (2)	C7—C6—C14—O3	98.3 (2)
O1—C1—C2—C3	177.8 (2)	C14—O3—C15—C16	−156.9 (4)
N1—C1—C2—C3	−2.8 (2)	C151—O3—C15—C16	−55.5 (10)
N1—N2—C3—C2	0.8 (3)	C14—O3—C151—C161	159.0 (3)
N1—N2—C3—C4	179.6 (2)	C15—O3—C151—C161	70.7 (11)
C5—C2—C3—N2	−177.6 (2)	N3—C5—C17—C22	83.2 (3)
C1—C2—C3—N2	1.3 (3)	C2—C5—C17—C22	−98.7 (3)
C5—C2—C3—C4	3.8 (5)	N3—C5—C17—C18	−100.26 (19)
C1—C2—C3—C4	−177.4 (3)	C2—C5—C17—C18	77.8 (2)
C6—N3—C5—C2	−177.0 (2)	C22—C17—C18—C19	−0.14 (18)
C6—N3—C5—C17	1.1 (3)	C5—C17—C18—C19	−176.7 (2)
C3—C2—C5—N3	−175.3 (2)	C17—C18—C19—C20	1.5 (3)
C1—C2—C5—N3	6.0 (4)	C18—C19—C20—C21	−1.3 (4)
C3—C2—C5—C17	6.7 (4)	C19—C20—C21—C22	−0.2 (4)
C1—C2—C5—C17	−172.0 (2)	C20—C21—C22—C17	1.6 (4)
C5—N3—C6—C14	62.5 (3)	C18—C17—C22—C21	−1.4 (3)
C5—N3—C6—C7	180.0 (2)	C5—C17—C22—C21	175.1 (2)
N3—C6—C7—C8	62.5 (3)	C1—N1—C23—C28	19.0 (4)
C14—C6—C7—C8	−177.0 (2)	N2—N1—C23—C28	−162.3 (2)
C6—C7—C8—C9	−110.9 (3)	C1—N1—C23—C24	−160.9 (2)
C6—C7—C8—C13	71.7 (3)	N2—N1—C23—C24	17.8 (3)
C13—C8—C9—C10	0.7 (4)	C28—C23—C24—C25	−1.6 (4)
C7—C8—C9—C10	−176.7 (2)	N1—C23—C24—C25	178.3 (2)
C8—C9—C10—C11	−0.8 (4)	C23—C24—C25—C26	0.7 (4)
C9—C10—C11—C12	0.4 (4)	C24—C25—C26—C27	0.3 (4)
C10—C11—C12—C13	0.2 (4)	C25—C26—C27—C28	−0.5 (4)
C11—C12—C13—C8	−0.3 (4)	C26—C27—C28—C23	−0.4 (4)
C9—C8—C13—C12	−0.2 (4)	C24—C23—C28—C27	1.4 (4)
C7—C8—C13—C12	177.2 (2)	N1—C23—C28—C27	−178.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.87	2.06	2.770 (2)	139