4-{N-[2-(1,3-Dioxo-1,3-dihydro­isoindol-2-yl)-3-phenyl­propion­yl]anilino}-1-phenethyl­piperidinium chloride methanol disolvate

The structure of the title compound, a fentanyl derivative with formula C₃₆H₃₆N₃O₃⁺·Cl⁻·2CH₃OH, crystallizes as a racemic mixture. The organic cation has an extended conformation and the structure displays O—H...O, O—H...Cl and N—H...Cl hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.067
• wR factor = 0.231
• Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      23.26 Deg.

Alert level B
THETM01_ALERT_3_B  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5556
PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6].....      23.26 Deg.
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C30
PLAT731_ALERT_1_B Bond    Calc     0.83(4), Rep    0.83(19) ......       4.75 su-Rat
              O4   -H4O     1.555   1.555
PLAT731_ALERT_1_B Bond    Calc     0.81(3), Rep    0.82(19) ......       6.33 su-Rat
              O5   -H5O     1.555   1.555

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C29
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C31
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT735_ALERT_1_C D-H     Calc     0.83(4), Rep   0.829(10) ......       4.00 su-Rat
              O4   -H4O     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.81(3), Rep   0.817(10) ......       3.00 su-Rat
              O5   -H5O     1.555   1.555

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

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: This work is the result of a collaborative project between two different departments at the University of Arizona involving synthetic chemistry and examination of pharmocological activity. Consequently there were three research students working on this project, and two principal investigators. The initial crystal structure determination was carried out by a crystallographer who has since left the University of Arizona. The structure was edited, modified and re-refined by a second crystallographer, who is also the corresponding author of the paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

4-{N-[2-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionyl]anilino}- 1-phenethylpiperidinium chloride methanol disolvate

Crystal data

C36H36N3O3^+·Cl^−·2CH4O	F(000) = 1400
Mr = 658.21	Dx = 1.237 Mg m^−3
Monoclinic, P21/c	Melting point: 479 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.014 (2) Å	Cell parameters from 2624 reflections
b = 17.131 (4) Å	θ = 2.2–22.6°
c = 19.055 (4) Å	µ = 0.15 mm^−1
β = 100.498 (7)°	T = 173 K
V = 3535.3 (12) Å^3	Block, colourless
Z = 4	0.45 × 0.32 × 0.27 mm

Data collection

Bruker SMART 1000 CCD diffractometer	3117 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.095
Graphite monochromator	θmax = 23.3°, θmin = 1.6°
thin–slice ω scans	h = −12→12
26495 measured reflections	k = −19→18
4996 independent reflections	l = −21→21

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)] = 0.067	Hydrogen site location: difference Fourier map
wR(F^2) = 0.231	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.1544P)^2] where P = (Fo^2 + 2Fc^2)/3
4996 reflections	(Δ/σ)max < 0.001
434 parameters	Δρmax = 0.52 e Å^−3
2 restraints	Δρmin = −0.56 e Å^−3

Special details

Experimental. Additional analytical data for (I)

1H NMR (CDCl3, 600 MHz, p.p.m.): 1.82 (d, 1H, J=13.2 Hz), 2.05 (m, 2H), 2.15 (qd, 1H, J1=3 Hz, J2=12.6 Hz), 2.40 (s, 2H), 2.99 (m, 2H), 3.17 (s, 4H), 3.32 (dd, 1H, J1=5.4 Hz, J2=14.4 Hz), 3.41 (m, 3H), 3.55 (br.m, 2H), 4.83 (tt, 1H, J1=3 Hz, J2=12 Hz), 4.97 (dd, 1H, J1=5.4 Hz, J2=10.2 Hz), 6.89 (d, 2H, J=7.2 Hz), 6.96 (d, 1H, J=7.8 Hz), 7.08 (m, 5H), 7.21 (m, 3H), 7.28 (m, 3H), 7.42 (t, 1H, J=7.2 Hz), 7.64 (br.s, 4H).13 C NMR (CDCl3, 600 MHz, p.p.m.): 27.2, 27.6, 30.2, 34.9, 50.3, 51.4, 51.9, 52.1, 53.6, 58.1, 123.2, 126.6, 127.2, 128.3, 128.7, 128.8, 128.9, 129.2, 129.3, 129.8, 130.2, 131.3, 134.1, 136.1, 136.3, 136.8, 166.9, 168.4.

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.

Despite containing a stereogenic centre this compound was crystallized as a racemic mixture and did not resolve into two enantiomers upon crystallization. The space group is P2₁/c. The c-glide plane was clearly identified by systematic absence data and so the correctness of the space group was verified by refining models in space groups with m point group symmetry. In all cases the refinement resulted in many highly correlated parameters and we are confident that the centrosymmetric P2₁/c is the correct space group.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl	0.99764 (12)	0.33004 (6)	0.46571 (8)	0.0719 (5)
O1	0.6649 (3)	0.22725 (15)	0.78818 (14)	0.0462 (8)
O2	0.4742 (3)	0.46303 (15)	0.73538 (13)	0.0434 (7)
O3	0.4286 (3)	0.38800 (15)	0.57316 (14)	0.0450 (8)
O4	0.4271 (4)	0.1701 (3)	0.5509 (2)	0.0944 (13)
H4O	0.356 (3)	0.164 (4)	0.528 (3)	0.113*
O5	0.1745 (3)	0.19250 (19)	0.51494 (17)	0.0630 (9)
H5O	0.151 (5)	0.2351 (15)	0.499 (3)	0.076*
N1	0.5575 (3)	0.33861 (16)	0.74457 (15)	0.0314 (8)
N2	0.6336 (3)	0.36983 (16)	0.60648 (14)	0.0337 (8)
N3	0.7897 (3)	0.44783 (17)	0.42702 (15)	0.0350 (8)
H3N	0.851 (4)	0.406 (2)	0.4350 (19)	0.042*
C1	0.6398 (4)	0.2954 (2)	0.7950 (2)	0.0376 (10)
C2	0.6833 (4)	0.3504 (2)	0.85489 (19)	0.0365 (10)
C3	0.7695 (4)	0.3390 (3)	0.9172 (2)	0.0497 (12)
H3	0.8129	0.2912	0.9272	0.060*
C4	0.7879 (5)	0.4024 (3)	0.9641 (2)	0.0576 (13)
H4	0.8454	0.3974	1.0076	0.069*
C5	0.7251 (5)	0.4721 (3)	0.9494 (2)	0.0553 (12)
H5	0.7403	0.5138	0.9827	0.066*
C6	0.6402 (4)	0.4822 (2)	0.8866 (2)	0.0483 (11)
H6	0.5965	0.5299	0.8763	0.058*
C7	0.6222 (4)	0.4201 (2)	0.84000 (19)	0.0367 (10)
C8	0.5402 (4)	0.4139 (2)	0.76863 (19)	0.0358 (10)
C9	0.4932 (4)	0.3066 (2)	0.67645 (19)	0.0377 (10)
H9	0.5309	0.2546	0.6701	0.045*
C10	0.3572 (4)	0.2932 (2)	0.6757 (2)	0.0451 (11)
H10A	0.3205	0.2669	0.6306	0.054*
H10B	0.3159	0.3445	0.6767	0.054*
C11	0.3318 (4)	0.2443 (2)	0.7381 (2)	0.0393 (10)
C12	0.3735 (4)	0.1678 (2)	0.7488 (2)	0.0519 (12)
H12	0.4195	0.1451	0.7164	0.062*
C13	0.3490 (4)	0.1238 (3)	0.8063 (3)	0.0569 (13)
H13	0.3778	0.0716	0.8130	0.068*
C14	0.2826 (5)	0.1572 (3)	0.8531 (3)	0.0613 (14)
H14	0.2659	0.1281	0.8927	0.074*
C15	0.2407 (5)	0.2321 (3)	0.8426 (3)	0.0662 (15)
H15	0.1937	0.2548	0.8745	0.079*
C16	0.2665 (5)	0.2748 (2)	0.7861 (2)	0.0520 (12)
H16	0.2380	0.3272	0.7802	0.062*
C17	0.5144 (4)	0.3585 (2)	0.61410 (19)	0.0342 (9)
C18	0.7350 (4)	0.3229 (2)	0.64281 (19)	0.0334 (9)
C19	0.7504 (4)	0.2458 (2)	0.62211 (19)	0.0377 (10)
H19	0.6931	0.2235	0.5841	0.045*
C20	0.8471 (4)	0.2027 (2)	0.6563 (2)	0.0419 (11)
H20	0.8550	0.1497	0.6430	0.050*
C21	0.9333 (4)	0.2347 (2)	0.7096 (2)	0.0452 (11)
H21	1.0017	0.2045	0.7321	0.054*
C22	0.9202 (4)	0.3116 (2)	0.7305 (2)	0.0433 (11)
H22	0.9793	0.3341	0.7675	0.052*
C23	0.8206 (4)	0.3549 (2)	0.69712 (19)	0.0370 (10)
H23	0.8109	0.4072	0.7117	0.044*
C24	0.6568 (4)	0.4168 (2)	0.54395 (17)	0.0342 (10)
H24	0.5945	0.4599	0.5361	0.041*
C25	0.7831 (4)	0.4536 (2)	0.55617 (19)	0.0350 (10)
H25A	0.8467	0.4123	0.5666	0.042*
H25B	0.7921	0.4886	0.5981	0.042*
C26	0.8038 (4)	0.5001 (2)	0.49120 (18)	0.0344 (10)
H26A	0.7432	0.5432	0.4821	0.041*
H26B	0.8877	0.5231	0.5004	0.041*
C27	0.6620 (4)	0.4137 (2)	0.41223 (19)	0.0371 (10)
H27A	0.6531	0.3793	0.3699	0.045*
H27B	0.6004	0.4562	0.4017	0.045*
C28	0.6376 (4)	0.3668 (2)	0.47646 (18)	0.0376 (10)
H28A	0.5519	0.3469	0.4667	0.045*
H28B	0.6941	0.3214	0.4840	0.045*
C29	0.8217 (4)	0.4900 (2)	0.36378 (19)	0.0384 (10)
H29A	0.9007	0.5183	0.3785	0.046*
H29B	0.7568	0.5290	0.3465	0.046*
C30	0.8336 (6)	0.4345 (3)	0.3040 (3)	0.081 (2)
H30A	0.8916	0.3922	0.3229	0.097*
H30B	0.7521	0.4104	0.2861	0.097*
C31	0.8783 (5)	0.4732 (2)	0.2432 (2)	0.0452 (11)
C32	0.7991 (4)	0.5133 (2)	0.1908 (2)	0.0517 (12)
H32	0.7145	0.5172	0.1946	0.062*
C33	0.8373 (7)	0.5476 (3)	0.1341 (2)	0.0657 (15)
H33	0.7804	0.5758	0.0999	0.079*
C34	0.9543 (8)	0.5413 (3)	0.1270 (3)	0.0780 (19)
H34	0.9804	0.5643	0.0869	0.094*
C35	1.0382 (5)	0.5020 (3)	0.1764 (3)	0.0685 (16)
H35	1.1218	0.4975	0.1706	0.082*
C36	0.9996 (5)	0.4685 (2)	0.2357 (3)	0.0559 (14)
H36	1.0577	0.4425	0.2710	0.067*
C37	0.4719 (6)	0.1469 (4)	0.4906 (4)	0.114 (3)
H37A	0.5168	0.1903	0.4736	0.171*
H37B	0.4027	0.1317	0.4531	0.171*
H37C	0.5278	0.1024	0.5025	0.171*
C38	0.1162 (5)	0.1637 (3)	0.5696 (3)	0.0685 (14)
H38A	0.0573	0.1228	0.5504	0.103*
H38B	0.0723	0.2064	0.5885	0.103*
H38C	0.1785	0.1420	0.6080	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0544 (9)	0.0395 (7)	0.1177 (12)	0.0071 (5)	0.0049 (8)	−0.0024 (6)
O1	0.054 (2)	0.0361 (16)	0.0494 (17)	0.0103 (13)	0.0103 (15)	0.0088 (13)
O2	0.0472 (18)	0.0371 (15)	0.0435 (16)	0.0084 (13)	0.0021 (14)	0.0049 (13)
O3	0.0438 (19)	0.0494 (16)	0.0392 (16)	0.0073 (14)	0.0005 (14)	0.0114 (13)
O4	0.082 (3)	0.117 (3)	0.084 (3)	0.023 (3)	0.016 (2)	−0.019 (2)
O5	0.068 (2)	0.067 (2)	0.057 (2)	0.0201 (19)	0.0184 (18)	0.0108 (17)
N1	0.0322 (19)	0.0327 (17)	0.0287 (16)	0.0021 (14)	0.0032 (14)	0.0039 (13)
N2	0.044 (2)	0.0316 (17)	0.0247 (17)	0.0000 (15)	0.0040 (15)	0.0031 (13)
N3	0.044 (2)	0.0268 (16)	0.0336 (18)	−0.0004 (15)	0.0048 (15)	0.0002 (14)
C1	0.037 (3)	0.042 (2)	0.035 (2)	0.0010 (19)	0.0089 (19)	0.0110 (18)
C2	0.034 (2)	0.046 (2)	0.031 (2)	−0.0071 (19)	0.0067 (18)	0.0089 (18)
C3	0.054 (3)	0.057 (3)	0.039 (2)	−0.003 (2)	0.008 (2)	0.015 (2)
C4	0.058 (3)	0.083 (3)	0.028 (2)	−0.013 (3)	−0.004 (2)	0.002 (2)
C5	0.061 (3)	0.063 (3)	0.040 (3)	−0.006 (3)	0.006 (2)	−0.009 (2)
C6	0.059 (3)	0.046 (2)	0.040 (2)	−0.006 (2)	0.010 (2)	−0.004 (2)
C7	0.039 (2)	0.040 (2)	0.031 (2)	−0.0053 (19)	0.0077 (18)	0.0024 (18)
C8	0.039 (3)	0.034 (2)	0.035 (2)	0.0003 (19)	0.0091 (19)	0.0063 (18)
C9	0.040 (3)	0.040 (2)	0.031 (2)	−0.0025 (19)	0.0025 (19)	−0.0004 (17)
C10	0.050 (3)	0.042 (2)	0.041 (2)	−0.006 (2)	0.003 (2)	−0.0010 (19)
C11	0.045 (3)	0.034 (2)	0.037 (2)	−0.0091 (19)	0.001 (2)	−0.0023 (18)
C12	0.056 (3)	0.049 (3)	0.052 (3)	−0.002 (2)	0.015 (2)	−0.008 (2)
C13	0.057 (3)	0.039 (2)	0.071 (3)	−0.006 (2)	0.002 (3)	0.010 (2)
C14	0.077 (4)	0.057 (3)	0.051 (3)	−0.015 (3)	0.016 (3)	0.009 (2)
C15	0.087 (4)	0.055 (3)	0.065 (3)	−0.008 (3)	0.036 (3)	−0.005 (2)
C16	0.064 (3)	0.037 (2)	0.057 (3)	0.001 (2)	0.018 (3)	0.000 (2)
C17	0.038 (3)	0.031 (2)	0.032 (2)	−0.0026 (19)	0.003 (2)	−0.0014 (17)
C18	0.037 (2)	0.032 (2)	0.030 (2)	0.0023 (17)	0.0042 (18)	0.0025 (16)
C19	0.050 (3)	0.035 (2)	0.027 (2)	−0.0006 (19)	0.0048 (19)	0.0019 (17)
C20	0.051 (3)	0.037 (2)	0.037 (2)	0.006 (2)	0.007 (2)	0.0000 (18)
C21	0.040 (3)	0.047 (2)	0.048 (3)	0.011 (2)	0.007 (2)	0.007 (2)
C22	0.041 (3)	0.049 (2)	0.037 (2)	−0.004 (2)	−0.002 (2)	0.0010 (19)
C23	0.040 (2)	0.035 (2)	0.034 (2)	0.0001 (19)	0.0020 (19)	−0.0012 (17)
C24	0.047 (3)	0.0292 (19)	0.025 (2)	−0.0008 (18)	0.0044 (18)	0.0014 (15)
C25	0.042 (3)	0.0302 (19)	0.031 (2)	0.0020 (17)	0.0012 (18)	−0.0008 (16)
C26	0.037 (2)	0.0285 (19)	0.036 (2)	−0.0056 (17)	0.0009 (18)	−0.0028 (17)
C27	0.050 (3)	0.032 (2)	0.029 (2)	−0.0053 (19)	0.0040 (19)	−0.0035 (16)
C28	0.048 (3)	0.032 (2)	0.031 (2)	−0.0080 (18)	0.0033 (19)	−0.0011 (16)
C29	0.054 (3)	0.0266 (19)	0.035 (2)	−0.0041 (18)	0.0097 (19)	0.0055 (17)
C30	0.162 (6)	0.037 (2)	0.061 (3)	−0.021 (3)	0.065 (4)	−0.006 (2)
C31	0.066 (3)	0.029 (2)	0.043 (3)	−0.003 (2)	0.015 (2)	−0.0077 (18)
C32	0.049 (3)	0.047 (2)	0.059 (3)	0.001 (2)	0.010 (2)	−0.017 (2)
C33	0.099 (5)	0.059 (3)	0.037 (3)	0.006 (3)	0.005 (3)	−0.003 (2)
C34	0.134 (6)	0.060 (3)	0.047 (3)	−0.026 (4)	0.034 (4)	−0.009 (3)
C35	0.062 (4)	0.070 (3)	0.085 (4)	−0.027 (3)	0.043 (3)	−0.039 (3)
C36	0.064 (4)	0.042 (2)	0.055 (3)	0.000 (2)	−0.006 (3)	−0.015 (2)
C37	0.075 (5)	0.145 (6)	0.130 (6)	−0.018 (4)	0.043 (4)	−0.077 (5)
C38	0.061 (4)	0.076 (3)	0.069 (3)	−0.006 (3)	0.012 (3)	0.012 (3)

Geometric parameters (Å, º)

O1—C1	1.212 (4)	C18—C23	1.380 (5)
O2—C8	1.212 (4)	C19—H19	0.950
O3—C17	1.220 (4)	C19—C20	1.361 (6)
O4—H4O	0.83 (19)	C20—H20	0.950
O4—C37	1.390 (7)	C20—C21	1.373 (6)
O5—H5O	0.82 (19)	C21—H21	0.950
O5—C38	1.409 (6)	C21—C22	1.390 (5)
N1—C1	1.406 (5)	C22—H22	0.950
N1—C8	1.394 (5)	C22—C23	1.380 (5)
N1—C9	1.467 (5)	C23—H23	0.950
N2—C17	1.360 (5)	C24—H24	1.000
N2—C18	1.447 (5)	C24—C25	1.507 (5)
N2—C24	1.498 (4)	C24—C28	1.527 (5)
N3—H3N	0.98 (4)	C25—H25A	0.990
N3—C26	1.501 (4)	C25—H25B	0.990
N3—C27	1.502 (5)	C25—C26	1.524 (5)
N3—C29	1.502 (5)	C26—H26A	0.990
C1—C2	1.490 (5)	C26—H26B	0.990
C2—C3	1.392 (6)	C27—H27A	0.990
C2—C7	1.375 (5)	C27—H27B	0.990
C3—H3	0.950	C27—C28	1.528 (5)
C3—C4	1.399 (6)	C28—H28A	0.990
C4—H4	0.950	C28—H28B	0.990
C4—C5	1.384 (6)	C29—H29A	0.990
C5—H5	0.950	C29—H29B	0.990
C5—C6	1.388 (6)	C29—C30	1.509 (5)
C6—H6	0.950	C30—H30A	0.990
C6—C7	1.377 (5)	C30—H30B	0.990
C7—C8	1.493 (5)	C30—C31	1.494 (6)
C9—H9	1.000	C31—C32	1.383 (6)
C9—C10	1.513 (6)	C31—C36	1.371 (6)
C9—C17	1.535 (5)	C32—H32	0.950
C10—H10A	0.990	C32—C33	1.362 (7)
C10—H10B	0.990	C33—H33	0.950
C10—C11	1.521 (6)	C33—C34	1.324 (8)
C11—C12	1.391 (5)	C34—H34	0.950
C11—C16	1.367 (6)	C34—C35	1.370 (8)
C12—H12	0.950	C35—H35	0.950
C12—C13	1.396 (6)	C35—C36	1.401 (7)
C13—H13	0.950	C36—H36	0.950
C13—C14	1.377 (7)	C37—H37A	0.980
C14—H14	0.950	C37—H37B	0.980
C14—C15	1.367 (7)	C37—H37C	0.980
C15—H15	0.950	C38—H38A	0.980
C15—C16	1.372 (6)	C38—H38B	0.980
C16—H16	0.950	C38—H38C	0.980
C18—C19	1.397 (5)
H4O—O4—C37	88 (5)	C20—C21—C22	119.8 (4)
H5O—O5—C38	116 (4)	H21—C21—C22	120.1
C1—N1—C8	111.8 (3)	C21—C22—H22	120.2
C1—N1—C9	123.7 (3)	C21—C22—C23	119.5 (4)
C8—N1—C9	124.3 (3)	H22—C22—C23	120.2
C17—N2—C18	123.1 (3)	C18—C23—C22	120.6 (4)
C17—N2—C24	118.0 (3)	C18—C23—H23	119.7
C18—N2—C24	116.8 (3)	C22—C23—H23	119.7
H3N—N3—C26	110 (2)	N2—C24—H24	107.6
H3N—N3—C27	110 (2)	N2—C24—C25	112.9 (3)
H3N—N3—C29	103 (2)	N2—C24—C28	110.6 (3)
C26—N3—C27	109.9 (3)	H24—C24—C25	107.6
C26—N3—C29	111.2 (3)	H24—C24—C28	107.6
C27—N3—C29	112.7 (3)	C25—C24—C28	110.3 (3)
O1—C1—N1	124.4 (4)	C24—C25—H25A	109.4
O1—C1—C2	130.1 (4)	C24—C25—H25B	109.4
N1—C1—C2	105.5 (3)	C24—C25—C26	111.3 (3)
C1—C2—C3	129.7 (4)	H25A—C25—H25B	108.0
C1—C2—C7	108.3 (3)	H25A—C25—C26	109.4
C3—C2—C7	122.0 (4)	H25B—C25—C26	109.4
C2—C3—H3	122.2	N3—C26—C25	110.0 (3)
C2—C3—C4	115.7 (4)	N3—C26—H26A	109.7
H3—C3—C4	122.2	N3—C26—H26B	109.7
C3—C4—H4	118.9	C25—C26—H26A	109.7
C3—C4—C5	122.1 (4)	C25—C26—H26B	109.7
H4—C4—C5	118.9	H26A—C26—H26B	108.2
C4—C5—H5	119.5	N3—C27—H27A	109.6
C4—C5—C6	121.1 (4)	N3—C27—H27B	109.6
H5—C5—C6	119.5	N3—C27—C28	110.4 (3)
C5—C6—H6	121.5	H27A—C27—H27B	108.1
C5—C6—C7	117.0 (4)	H27A—C27—C28	109.6
H6—C6—C7	121.5	H27B—C27—C28	109.6
C2—C7—C6	122.0 (4)	C24—C28—C27	111.2 (3)
C2—C7—C8	108.6 (3)	C24—C28—H28A	109.4
C6—C7—C8	129.4 (4)	C24—C28—H28B	109.4
O2—C8—N1	125.1 (3)	C27—C28—H28A	109.4
O2—C8—C7	129.2 (3)	C27—C28—H28B	109.4
N1—C8—C7	105.6 (3)	H28A—C28—H28B	108.0
N1—C9—H9	107.2	N3—C29—H29A	109.3
N1—C9—C10	112.4 (3)	N3—C29—H29B	109.3
N1—C9—C17	110.6 (3)	N3—C29—C30	111.6 (3)
H9—C9—C10	107.2	H29A—C29—H29B	108.0
H9—C9—C17	107.2	H29A—C29—C30	109.3
C10—C9—C17	111.8 (3)	H29B—C29—C30	109.3
C9—C10—H10A	108.9	C29—C30—H30A	109.0
C9—C10—H10B	108.9	C29—C30—H30B	109.0
C9—C10—C11	113.5 (3)	C29—C30—C31	113.1 (3)
H10A—C10—H10B	107.7	H30A—C30—H30B	107.8
H10A—C10—C11	108.9	H30A—C30—C31	109.0
H10B—C10—C11	108.9	H30B—C30—C31	109.0
C10—C11—C12	122.1 (4)	C30—C31—C32	121.7 (5)
C10—C11—C16	120.4 (4)	C30—C31—C36	121.3 (5)
C12—C11—C16	117.5 (4)	C32—C31—C36	117.0 (4)
C11—C12—H12	119.4	C31—C32—H32	118.6
C11—C12—C13	121.2 (4)	C31—C32—C33	122.8 (5)
H12—C12—C13	119.4	H32—C32—C33	118.6
C12—C13—H13	120.5	C32—C33—H33	120.2
C12—C13—C14	119.1 (4)	C32—C33—C34	119.5 (5)
H13—C13—C14	120.5	H33—C33—C34	120.2
C13—C14—H14	120.0	C33—C34—H34	119.4
C13—C14—C15	120.0 (4)	C33—C34—C35	121.1 (5)
H14—C14—C15	120.0	H34—C34—C35	119.4
C14—C15—H15	119.9	C34—C35—H35	120.3
C14—C15—C16	120.2 (5)	C34—C35—C36	119.3 (5)
H15—C15—C16	119.9	H35—C35—C36	120.3
C11—C16—C15	122.0 (4)	C31—C36—C35	120.3 (5)
C11—C16—H16	119.0	C31—C36—H36	119.9
C15—C16—H16	119.0	C35—C36—H36	119.9
O3—C17—N2	121.5 (3)	O4—C37—H37A	109.5
O3—C17—C9	121.7 (4)	O4—C37—H37B	109.5
N2—C17—C9	116.8 (3)	O4—C37—H37C	109.5
N2—C18—C19	120.8 (3)	H37A—C37—H37B	109.5
N2—C18—C23	120.1 (3)	H37A—C37—H37C	109.5
C19—C18—C23	119.1 (4)	H37B—C37—H37C	109.5
C18—C19—H19	119.9	O5—C38—H38A	109.5
C18—C19—C20	120.2 (4)	O5—C38—H38B	109.5
H19—C19—C20	119.9	O5—C38—H38C	109.5
C19—C20—H20	119.6	H38A—C38—H38B	109.5
C19—C20—C21	120.8 (4)	H38A—C38—H38C	109.5
H20—C20—C21	119.6	H38B—C38—H38C	109.5
C20—C21—H21	120.1
C8—N1—C1—O1	176.0 (4)	C24—N2—C17—O3	−2.8 (5)
C8—N1—C1—C2	−3.2 (4)	C24—N2—C17—C9	176.9 (3)
C9—N1—C1—O1	−1.2 (6)	N1—C9—C17—O3	−121.7 (4)
C9—N1—C1—C2	179.6 (3)	N1—C9—C17—N2	58.5 (4)
O1—C1—C2—C3	3.9 (7)	C10—C9—C17—O3	4.4 (5)
O1—C1—C2—C7	−175.9 (4)	C10—C9—C17—N2	−175.4 (3)
N1—C1—C2—C3	−177.1 (4)	C17—N2—C18—C19	72.5 (5)
N1—C1—C2—C7	3.2 (4)	C17—N2—C18—C23	−109.6 (4)
C1—C2—C3—C4	−178.5 (4)	C24—N2—C18—C19	−90.4 (4)
C7—C2—C3—C4	1.2 (6)	C24—N2—C18—C23	87.5 (4)
C2—C3—C4—C5	−0.4 (7)	N2—C18—C19—C20	179.3 (4)
C3—C4—C5—C6	0.0 (7)	C23—C18—C19—C20	1.4 (6)
C4—C5—C6—C7	−0.3 (7)	C18—C19—C20—C21	−2.4 (6)
C1—C2—C7—C6	178.2 (4)	C19—C20—C21—C22	1.8 (6)
C1—C2—C7—C8	−2.1 (4)	C20—C21—C22—C23	−0.2 (6)
C3—C2—C7—C6	−1.6 (6)	C21—C22—C23—C18	−0.7 (6)
C3—C2—C7—C8	178.1 (4)	N2—C18—C23—C22	−177.7 (4)
C5—C6—C7—C2	1.1 (6)	C19—C18—C23—C22	0.2 (6)
C5—C6—C7—C8	−178.6 (4)	C17—N2—C24—C25	155.9 (3)
C1—N1—C8—O2	179.8 (4)	C17—N2—C24—C28	−80.1 (4)
C1—N1—C8—C7	1.9 (4)	C18—N2—C24—C25	−40.3 (4)
C9—N1—C8—O2	−3.0 (6)	C18—N2—C24—C28	83.8 (4)
C9—N1—C8—C7	179.1 (3)	N2—C24—C25—C26	179.4 (3)
C2—C7—C8—O2	−177.5 (4)	C28—C24—C25—C26	55.2 (4)
C2—C7—C8—N1	0.2 (4)	C27—N3—C26—C25	60.1 (4)
C6—C7—C8—O2	2.2 (7)	C29—N3—C26—C25	−174.4 (3)
C6—C7—C8—N1	179.9 (4)	C24—C25—C26—N3	−58.7 (4)
C1—N1—C9—C10	107.3 (4)	C26—N3—C27—C28	−59.2 (4)
C1—N1—C9—C17	−127.0 (4)	C29—N3—C27—C28	176.1 (3)
C8—N1—C9—C10	−69.6 (4)	N2—C24—C28—C27	−179.5 (3)
C8—N1—C9—C17	56.2 (5)	C25—C24—C28—C27	−54.0 (4)
N1—C9—C10—C11	−53.0 (4)	N3—C27—C28—C24	56.4 (4)
C17—C9—C10—C11	−178.1 (3)	C26—N3—C29—C30	168.2 (4)
C9—C10—C11—C12	−61.5 (5)	C27—N3—C29—C30	−67.9 (5)
C9—C10—C11—C16	118.3 (4)	N3—C29—C30—C31	−174.0 (4)
C10—C11—C12—C13	−179.9 (4)	C29—C30—C31—C32	−82.3 (6)
C16—C11—C12—C13	0.3 (6)	C29—C30—C31—C36	99.6 (5)
C11—C12—C13—C14	−0.2 (7)	C30—C31—C32—C33	−178.5 (4)
C12—C13—C14—C15	0.6 (7)	C36—C31—C32—C33	−0.3 (6)
C13—C14—C15—C16	−1.1 (8)	C31—C32—C33—C34	1.6 (7)
C10—C11—C16—C15	179.3 (4)	C32—C33—C34—C35	−1.2 (7)
C12—C11—C16—C15	−0.9 (7)	C33—C34—C35—C36	−0.5 (7)
C14—C15—C16—C11	1.3 (8)	C30—C31—C36—C35	176.8 (4)
C18—N2—C17—O3	−165.6 (3)	C32—C31—C36—C35	−1.4 (6)
C18—N2—C17—C9	14.2 (5)	C34—C35—C36—C31	1.8 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O5	0.83 (1)	2.03 (4)	2.769 (6)	148 (7)
O5—H5O···Cl^i	0.82 (1)	2.34 (3)	3.092 (3)	152 (5)
N3—H3N···Cl	0.98 (4)	2.07 (4)	3.041 (4)	170 (3)

Symmetry code: (i) x−1, y, z.