(5R,6R,7R,9R,13R,14S)-21-Cyclo­propyl­meth­yl-6,14-endo-ethano-2',3',4',5',7,8-hexa­hydro-4',4',5',5'-tetra­methyl­furano[2',3'6,7]normorphide hydro­chloride methanol solvate

The title compound, C₂₈H₃₈NO₃⁺·Cl^-·CH₄O, is demeth­oxy-buprenorphine hydro­chloride (buprenorphine degradation product). Crystal structure determination has confirmed that the elimination of methanol and rearrangement with the formation of a new ring proceeds with the retention of chirality of all chiral centres of the mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.049
• Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.54 Ratio
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N17    -   H171   ...       1.01 Ang.
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O4     -   H541   ...       1.02 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H81    ..  H171    ..       1.94 Ang.

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           76.86
           From the CIF: _reflns_number_total               5505
           Count of symmetry unique reflns         3191
           Completeness (_total/calc)            172.52%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2314
           Fraction of Friedel pairs measured     0.725
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CrysAlis RED (Oxford Diffraction, 2002); cell refinement: CrysAlis RED; data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CRYSTALS.

(5R,6R,7R,9R,13R,14S)-21-Cyclopropylmethyl-6,14-endo-ethano- 2',3',4',5',7,8-hexahydro-4',4',5',5'-tetramethylfurano- [2',3'6,7]normorphide hydrochloride methanol solvate

Crystal data

C28H38NO3^+·Cl^−·CH4O	F(000) = 1088
Mr = 504.11	Dx = 1.247 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 16127 reflections
a = 11.5861 (5) Å	θ = 5–77°
b = 13.7665 (7) Å	µ = 1.53 mm^−1
c = 16.8391 (8) Å	T = 295 K
V = 2685.8 (2) Å^3	Prism, colourless
Z = 4	0.32 × 0.23 × 0.14 mm

Data collection

Oxford Diffraction XCALIBUR diffractometer	4754 reflections with I > 1.96u(I)
Graphite monochromator	Rint = 0.090
φ and ω scans	θmax = 76.9°, θmin = 4.6°
Absorption correction: numerical (de Meulenaer & Tompa, 1965)	h = −14→14
Tmin = 0.58, Tmax = 0.81	k = −17→16
29111 measured reflections	l = −20→20
5505 independent reflections

Refinement

Refinement on F	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	Weighting scheme using Chebychev polynomial (Watkin et al., 1994; Prince, 1982): W = [weight] * [1-(ΔF/6*σF)^2]^2; [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1*Tn-1(x)], where Ai are the Chebychev coefficients (13.3 -3.19 10.8) and x = F /Fmax.
R[F^2 > 2σ(F^2)] = 0.041	(Δ/σ)max = 0.000329
wR(F^2) = 0.049	Δρmax = 0.40 e Å^−3
S = 1.08	Δρmin = −0.34 e Å^−3
4754 reflections	Extinction correction: Larson (1970)
474 parameters	Extinction coefficient: 219 (18)
165 restraints	Absolute structure: Flack (1983), 1563 Friedel-pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.016 (14)
Hydrogen site location: inferred from neighbouring sites

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

	x	y	z	Uiso*/Ueq
O1	0.79271 (15)	0.42322 (15)	0.71054 (12)	0.0758
O2	0.54608 (11)	0.41244 (10)	0.69597 (8)	0.0469
O3	0.36531 (12)	0.37119 (12)	0.56523 (8)	0.0513
O4	1.0056 (2)	0.45182 (19)	0.77135 (16)	0.0948
C1	0.71086 (16)	0.22008 (14)	0.84344 (11)	0.0445
C2	0.77885 (16)	0.28784 (16)	0.80291 (12)	0.0519
C3	0.73007 (16)	0.35888 (16)	0.75393 (12)	0.0499
C4	0.61119 (15)	0.35964 (13)	0.74871 (10)	0.0398
C5	0.42655 (15)	0.38128 (12)	0.70563 (10)	0.0384
C6	0.37579 (14)	0.32117 (14)	0.63834 (9)	0.0384
C7	0.25154 (14)	0.30072 (12)	0.66588 (10)	0.0366
C8	0.24640 (14)	0.22244 (13)	0.73081 (10)	0.0379
C9	0.38249 (14)	0.15844 (11)	0.84396 (9)	0.0321
C10	0.50929 (15)	0.14738 (12)	0.87152 (10)	0.0365
C11	0.59130 (14)	0.22496 (12)	0.84052 (9)	0.0356
C12	0.54607 (13)	0.29968 (12)	0.79643 (9)	0.0339
C13	0.42182 (13)	0.31569 (10)	0.78026 (9)	0.0312
C14	0.36955 (13)	0.21414 (11)	0.76494 (9)	0.0315
C15	0.36160 (15)	0.36757 (12)	0.84933 (11)	0.0388
C16	0.36056 (15)	0.30855 (13)	0.92445 (10)	0.0390
N17	0.31191 (11)	0.20995 (10)	0.90705 (8)	0.0342
C18	0.44919 (16)	0.22976 (14)	0.62722 (10)	0.0421
C19	0.43931 (16)	0.16211 (12)	0.69940 (9)	0.0386
C20	0.18227 (15)	0.29402 (14)	0.58778 (11)	0.0433
C21	0.24574 (17)	0.37524 (16)	0.53928 (11)	0.0487
C22	0.1890 (2)	0.19542 (17)	0.54720 (14)	0.0594
C23	0.05540 (17)	0.31603 (18)	0.60223 (14)	0.0547
C24	0.2475 (3)	0.3620 (3)	0.45043 (14)	0.0794
C25	0.2036 (3)	0.47770 (18)	0.5579 (2)	0.0718
C26	0.29374 (16)	0.15381 (15)	0.98258 (10)	0.0452
C27	0.2358 (2)	0.05876 (15)	0.96940 (14)	0.0553
C28	0.1128 (3)	0.0588 (2)	0.94334 (18)	0.0733
C29	0.1428 (3)	0.03255 (18)	1.02698 (18)	0.0719
C30	1.0443 (4)	0.5470 (3)	0.7811 (3)	0.1090
Cl1	0.07115 (4)	0.31639 (5)	0.90754 (4)	0.0658
H11	0.7489 (15)	0.1702 (10)	0.8739 (7)	0.0528 (19)*
H21	0.8620 (14)	0.2876 (11)	0.8097 (8)	0.0623 (19)*
H51	0.3785 (15)	0.4404 (12)	0.7125 (11)	0.0463 (19)*
H71	0.2242 (15)	0.3602 (11)	0.6916 (10)	0.0433 (19)*
H81	0.1899 (14)	0.2408 (12)	0.7725 (10)	0.0467 (19)*
H82	0.2213 (16)	0.1587 (11)	0.7090 (10)	0.0452 (19)*
H91	0.3483 (15)	0.0931 (11)	0.8386 (10)	0.0393 (18)*
H101	0.5112 (15)	0.1473 (13)	0.9291 (9)	0.0429 (19)*
H102	0.5370 (15)	0.0847 (11)	0.8536 (10)	0.0432 (19)*
H151	0.4037 (16)	0.4283 (12)	0.8587 (10)	0.0483 (19)*
H152	0.2821 (14)	0.3832 (13)	0.8313 (10)	0.0472 (19)*
H161	0.3101 (15)	0.3366 (12)	0.9650 (10)	0.0471 (19)*
H162	0.4366 (14)	0.3006 (13)	0.9475 (11)	0.0464 (19)*
H181	0.5291 (14)	0.2501 (13)	0.6211 (11)	0.0525 (19)*
H182	0.4240 (16)	0.1952 (12)	0.5791 (10)	0.0494 (19)*
H191	0.5185 (14)	0.1412 (13)	0.7198 (10)	0.0452 (19)*
H192	0.3965 (15)	0.1034 (12)	0.6840 (10)	0.0480 (19)*
H221	0.1391 (19)	0.1897 (18)	0.4998 (12)	0.0720 (19)*
H222	0.166 (2)	0.1438 (15)	0.5838 (13)	0.0698 (19)*
H223	0.2691 (16)	0.1789 (18)	0.5289 (14)	0.0727 (19)*
H231	0.015 (2)	0.3211 (16)	0.5515 (11)	0.0660 (19)*
H232	0.046 (2)	0.3765 (13)	0.6315 (12)	0.0651 (19)*
H233	0.028 (2)	0.2604 (14)	0.6335 (12)	0.0669 (19)*
H241	0.1701 (18)	0.3666 (19)	0.4249 (17)	0.0951 (19)*
H242	0.297 (2)	0.4123 (17)	0.4266 (17)	0.0949 (19)*
H243	0.282 (2)	0.2974 (15)	0.4383 (18)	0.0937 (19)*
H251	0.1310 (18)	0.486 (2)	0.5281 (14)	0.0865 (19)*
H252	0.191 (2)	0.4879 (19)	0.6170 (11)	0.0859 (19)*
H253	0.261 (2)	0.5229 (18)	0.5370 (14)	0.0862 (19)*
H261	0.3683 (15)	0.1410 (13)	1.0079 (11)	0.0546 (19)*
H262	0.2458 (16)	0.1950 (13)	1.0162 (11)	0.0544 (19)*
H271	0.2818 (16)	0.0060 (13)	0.9470 (13)	0.0658 (19)*
H281	0.076 (2)	0.1238 (14)	0.9325 (13)	0.0882 (19)*
H282	0.087 (2)	0.0107 (14)	0.9033 (13)	0.0882 (19)*
H291	0.122 (2)	0.0775 (14)	1.0694 (11)	0.0857 (19)*
H292	0.133 (2)	−0.0342 (13)	1.0454 (12)	0.0865 (19)*
H171	0.234 (2)	0.2237 (15)	0.8830 (13)	0.041 (5)*
H511	0.861 (3)	0.427 (2)	0.735 (2)	0.087 (10)*
H541	1.031 (4)	0.412 (3)	0.819 (3)	0.129 (15)*
H301	1.0194	0.5865	0.7344	0.1295*
H302	1.1303	0.5471	0.7847	0.1295*
H303	1.0109	0.5753	0.8307	0.1295*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0395 (8)	0.1066 (14)	0.0814 (11)	−0.0249 (9)	−0.0057 (8)	0.0449 (11)
O2	0.0350 (7)	0.0524 (7)	0.0534 (7)	−0.0097 (5)	−0.0042 (5)	0.0209 (6)
O3	0.0413 (7)	0.0699 (9)	0.0427 (7)	−0.0022 (6)	−0.0052 (5)	0.0226 (6)
O4	0.0868 (15)	0.0982 (15)	0.0994 (16)	−0.0272 (12)	−0.0330 (13)	0.0202 (13)
C1	0.0348 (8)	0.0552 (10)	0.0434 (9)	0.0051 (8)	−0.0044 (7)	0.0046 (8)
C2	0.0284 (8)	0.0744 (13)	0.0528 (10)	−0.0007 (8)	−0.0018 (7)	0.0122 (10)
C3	0.0329 (9)	0.0657 (11)	0.0512 (10)	−0.0097 (8)	0.0012 (7)	0.0141 (9)
C4	0.0317 (8)	0.0455 (9)	0.0421 (8)	−0.0044 (6)	−0.0025 (6)	0.0074 (7)
C5	0.0311 (7)	0.0382 (8)	0.0458 (9)	−0.0022 (6)	0.0001 (7)	0.0102 (7)
C6	0.0356 (8)	0.0470 (9)	0.0325 (8)	0.0007 (7)	−0.0002 (6)	0.0104 (7)
C7	0.0321 (7)	0.0415 (8)	0.0361 (8)	0.0008 (6)	−0.0031 (6)	0.0035 (7)
C8	0.0345 (8)	0.0442 (8)	0.0349 (8)	−0.0049 (7)	−0.0015 (6)	0.0033 (6)
C9	0.0345 (7)	0.0308 (7)	0.0312 (7)	−0.0020 (6)	0.0018 (6)	−0.0001 (6)
C10	0.0375 (8)	0.0357 (8)	0.0363 (8)	0.0028 (6)	0.0001 (6)	0.0041 (6)
C11	0.0335 (8)	0.0396 (8)	0.0337 (7)	0.0021 (6)	−0.0013 (6)	0.0011 (6)
C12	0.0307 (7)	0.0353 (7)	0.0358 (8)	−0.0017 (6)	−0.0004 (6)	−0.0013 (6)
C13	0.0291 (7)	0.0304 (7)	0.0340 (7)	0.0006 (6)	−0.0003 (6)	0.0020 (6)
C14	0.0332 (7)	0.0311 (7)	0.0301 (7)	−0.0007 (6)	0.0005 (6)	−0.0008 (6)
C15	0.0382 (8)	0.0335 (7)	0.0446 (9)	−0.0001 (6)	0.0029 (7)	−0.0065 (7)
C16	0.0383 (8)	0.0389 (8)	0.0397 (8)	−0.0042 (6)	0.0051 (6)	−0.0091 (7)
N17	0.0329 (6)	0.0383 (6)	0.0313 (6)	−0.0022 (5)	0.0021 (5)	−0.0015 (5)
C18	0.0394 (9)	0.0543 (10)	0.0327 (7)	0.0059 (8)	0.0035 (6)	0.0024 (8)
C19	0.0432 (9)	0.0404 (8)	0.0323 (7)	0.0027 (7)	0.0021 (6)	−0.0025 (6)
C20	0.0378 (9)	0.0505 (9)	0.0417 (9)	0.0017 (7)	−0.0080 (7)	0.0046 (8)
C21	0.0392 (9)	0.0613 (11)	0.0456 (9)	0.0013 (8)	−0.0073 (7)	0.0162 (8)
C22	0.0683 (14)	0.0566 (11)	0.0532 (12)	0.0027 (10)	−0.0167 (10)	−0.0101 (10)
C23	0.0388 (9)	0.0681 (13)	0.0572 (11)	0.0024 (9)	−0.0093 (8)	0.0063 (10)
C24	0.0777 (18)	0.113 (2)	0.0472 (12)	−0.0155 (16)	−0.0130 (11)	0.0219 (13)
C25	0.0631 (15)	0.0551 (12)	0.097 (2)	0.0055 (11)	−0.0008 (14)	0.0245 (13)
C26	0.0375 (9)	0.0636 (11)	0.0344 (8)	−0.0024 (8)	0.0017 (7)	0.0078 (8)
C27	0.0616 (13)	0.0454 (10)	0.0588 (11)	0.0041 (9)	0.0238 (10)	0.0097 (9)
C28	0.0692 (16)	0.0678 (15)	0.0830 (17)	−0.0269 (12)	0.0154 (13)	−0.0095 (13)
C29	0.0825 (18)	0.0506 (11)	0.0825 (17)	−0.0040 (11)	0.0409 (15)	0.0123 (12)
C30	0.110 (3)	0.087 (2)	0.130 (3)	0.002 (2)	−0.040 (2)	−0.017 (2)
Cl1	0.0439 (2)	0.0884 (4)	0.0650 (3)	0.0195 (3)	0.0088 (2)	0.0094 (3)

Geometric parameters (Å, º)

O1—C3	1.358 (2)	C16—N17	1.499 (2)
O1—H511	0.89 (4)	C16—H161	0.979 (15)
O2—C4	1.373 (2)	C16—H162	0.969 (16)
O2—C5	1.459 (2)	N17—C26	1.503 (2)
O3—C6	1.416 (2)	N17—H171	1.00 (2)
O3—C21	1.454 (2)	C18—C19	1.535 (2)
O4—C30	1.394 (5)	C18—H181	0.972 (16)
O4—H541	1.02 (5)	C18—H182	0.984 (15)
C1—C2	1.399 (3)	C19—H191	1.021 (15)
C1—C11	1.388 (2)	C19—H192	0.983 (15)
C1—H11	0.963 (16)	C20—C21	1.568 (3)
C2—C3	1.399 (3)	C20—C22	1.522 (3)
C2—H21	0.971 (16)	C20—C23	1.520 (3)
C3—C4	1.380 (2)	C21—C24	1.507 (3)
C4—C12	1.377 (2)	C21—C25	1.525 (3)
C5—C6	1.522 (2)	C22—H221	0.989 (17)
C5—C13	1.548 (2)	C22—H222	0.976 (17)
C5—H51	0.994 (15)	C22—H223	1.004 (17)
C6—C7	1.538 (2)	C23—H231	0.978 (17)
C6—C18	1.530 (2)	C23—H232	0.974 (16)
C7—C8	1.536 (2)	C23—H233	0.982 (17)
C7—C20	1.543 (2)	C24—H241	0.996 (18)
C7—H71	0.979 (15)	C24—H242	0.984 (18)
C8—C14	1.542 (2)	C24—H243	0.996 (18)
C8—H81	0.993 (15)	C25—H251	0.985 (18)
C8—H82	0.995 (15)	C25—H252	1.016 (17)
C9—C10	1.548 (2)	C25—H253	0.975 (17)
C9—C14	1.543 (2)	C26—C27	1.487 (3)
C9—N17	1.517 (2)	C26—H261	0.980 (16)
C9—H91	0.987 (15)	C26—H262	0.975 (16)
C10—C11	1.522 (2)	C27—C28	1.491 (4)
C10—H101	0.970 (15)	C27—C29	1.493 (3)
C10—H102	0.969 (15)	C27—H271	0.978 (17)
C11—C12	1.373 (2)	C28—C29	1.495 (4)
C12—C13	1.482 (2)	C28—H281	1.008 (17)
C13—C14	1.545 (2)	C28—H282	0.992 (17)
C13—C15	1.533 (2)	C29—H291	0.977 (17)
C14—C19	1.544 (2)	C29—H292	0.976 (17)
C15—C16	1.503 (3)	C30—H301	0.999
C15—H151	0.980 (15)	C30—H302	0.999
C15—H152	0.993 (16)	C30—H303	1.001
C3—O1—H511	105 (2)	C9—N17—C26	115.34 (13)
C4—O2—C5	107.08 (12)	C16—N17—C26	110.67 (13)
C6—O3—C21	111.20 (13)	C9—N17—H171	106.8 (12)
C30—O4—H541	109 (3)	C16—N17—H171	104.1 (12)
C2—C1—C11	120.84 (17)	C26—N17—H171	108.3 (12)
C2—C1—H11	118.5 (10)	C6—C18—C19	111.13 (13)
C11—C1—H11	120.7 (10)	C6—C18—H181	107.7 (11)
C1—C2—C3	121.77 (17)	C19—C18—H181	109.3 (11)
C1—C2—H21	119.9 (10)	C6—C18—H182	109.5 (10)
C3—C2—H21	118.3 (10)	C19—C18—H182	109.6 (10)
C2—C3—O1	123.87 (18)	H181—C18—H182	109.5 (13)
C2—C3—C4	116.50 (17)	C14—C19—C18	108.87 (13)
O1—C3—C4	119.60 (18)	C14—C19—H191	111.1 (10)
C3—C4—O2	126.40 (16)	C18—C19—H191	111.7 (10)
C3—C4—C12	120.33 (16)	C14—C19—H192	107.8 (10)
O2—C4—C12	113.18 (15)	C18—C19—H192	109.1 (10)
O2—C5—C6	116.34 (15)	H191—C19—H192	108.0 (13)
O2—C5—C13	107.19 (13)	C7—C20—C21	99.06 (14)
C6—C5—C13	105.88 (13)	C7—C20—C22	114.16 (16)
O2—C5—H51	107.7 (10)	C21—C20—C22	112.23 (18)
C6—C5—H51	108.4 (10)	C7—C20—C23	110.76 (16)
C13—C5—H51	111.3 (11)	C21—C20—C23	113.25 (16)
C5—C6—O3	114.59 (15)	C22—C20—C23	107.40 (17)
C5—C6—C7	103.69 (13)	C20—C21—O3	105.25 (14)
O3—C6—C7	105.72 (13)	C20—C21—C24	115.9 (2)
C5—C6—C18	108.88 (14)	O3—C21—C24	106.29 (19)
O3—C6—C18	109.95 (14)	C20—C21—C25	113.73 (19)
C7—C6—C18	113.98 (15)	O3—C21—C25	106.21 (19)
C6—C7—C8	112.29 (13)	C24—C21—C25	108.6 (2)
C6—C7—C20	103.92 (13)	C20—C22—H221	113.8 (15)
C8—C7—C20	122.98 (14)	C20—C22—H222	110.6 (15)
C6—C7—H71	106.4 (11)	H221—C22—H222	107.2 (15)
C8—C7—H71	105.0 (10)	C20—C22—H223	112.8 (15)
C20—C7—H71	105.0 (10)	H221—C22—H223	105.9 (15)
C7—C8—C14	106.33 (13)	H222—C22—H223	106.0 (15)
C7—C8—H81	110.5 (10)	C20—C23—H231	109.9 (14)
C14—C8—H81	111.4 (10)	C20—C23—H232	111.4 (15)
C7—C8—H82	111.5 (10)	H231—C23—H232	109.0 (15)
C14—C8—H82	110.0 (10)	C20—C23—H233	103.9 (15)
H81—C8—H82	107.1 (13)	H231—C23—H233	111.8 (15)
C10—C9—C14	113.55 (12)	H232—C23—H233	110.9 (15)
C10—C9—N17	110.34 (12)	C21—C24—H241	114.0 (18)
C14—C9—N17	108.63 (12)	C21—C24—H242	109.2 (18)
C10—C9—H91	108.5 (10)	H241—C24—H242	107.6 (16)
C14—C9—H91	109.6 (10)	C21—C24—H243	108.4 (18)
N17—C9—H91	105.9 (10)	H241—C24—H243	109.3 (16)
C9—C10—C11	114.87 (13)	H242—C24—H243	108.2 (16)
C9—C10—H101	108.8 (10)	C21—C25—H251	105.8 (16)
C11—C10—H101	109.2 (10)	C21—C25—H252	112.0 (16)
C9—C10—H102	108.0 (11)	H251—C25—H252	111.1 (16)
C11—C10—H102	108.1 (10)	C21—C25—H253	107.4 (17)
H101—C10—H102	107.7 (13)	H251—C25—H253	109.0 (16)
C10—C11—C1	125.25 (15)	H252—C25—H253	111.3 (16)
C10—C11—C12	118.24 (14)	N17—C26—C27	112.91 (16)
C1—C11—C12	115.88 (15)	N17—C26—H261	109.7 (11)
C4—C12—C11	123.76 (15)	C27—C26—H261	107.7 (11)
C4—C12—C13	109.63 (14)	N17—C26—H262	105.8 (11)
C11—C12—C13	125.58 (14)	C27—C26—H262	109.9 (11)
C5—C13—C12	101.63 (12)	H261—C26—H262	110.8 (13)
C5—C13—C14	113.95 (13)	C26—C27—C28	118.4 (2)
C12—C13—C14	106.07 (12)	C26—C27—C29	116.19 (19)
C5—C13—C15	111.12 (13)	C28—C27—C29	60.13 (19)
C12—C13—C15	111.86 (13)	C26—C27—H271	117.7 (10)
C14—C13—C15	111.70 (13)	C28—C27—H271	114.1 (12)
C8—C14—C9	116.61 (13)	C29—C27—H271	117.7 (11)
C8—C14—C13	110.96 (13)	C27—C28—C29	60.01 (18)
C9—C14—C13	105.51 (12)	C27—C28—H281	117.3 (13)
C8—C14—C19	104.61 (13)	C29—C28—H281	118.9 (13)
C9—C14—C19	109.58 (12)	C27—C28—H282	119.4 (13)
C13—C14—C19	109.51 (12)	C29—C28—H282	123.3 (12)
C13—C15—C16	112.97 (14)	H281—C28—H282	109.9 (14)
C13—C15—H151	107.0 (10)	C28—C29—C27	59.86 (18)
C16—C15—H151	109.3 (10)	C28—C29—H291	118.5 (13)
C13—C15—H152	106.9 (10)	C27—C29—H291	120.3 (13)
C16—C15—H152	111.5 (10)	C28—C29—H292	120.1 (13)
H151—C15—H152	109.0 (13)	C27—C29—H292	121.0 (13)
C15—C16—N17	109.15 (13)	H291—C29—H292	109.5 (13)
C15—C16—H161	112.2 (10)	O4—C30—H301	109.111
N17—C16—H161	105.6 (10)	O4—C30—H302	109.268
C15—C16—H162	113.0 (10)	H301—C30—H302	109.630
N17—C16—H162	108.6 (11)	O4—C30—H303	109.851
H161—C16—H162	108.0 (13)	H301—C30—H303	109.487
C9—N17—C16	110.95 (12)	H302—C30—H303	109.480

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H171···Cl1	1.00 (2)	2.32 (2)	3.151 (1)	140 (2)
O1—H511···O4	0.89 (4)	1.82 (3)	2.700 (3)	170 (3)
O4—H541···Cl1^i	1.02 (5)	2.04 (5)	3.052 (3)	172 (4)

Symmetry code: (i) x+1, y, z.