N-[(2'-Cyano­bi­phenyl-4-yl)­methyl]-L-valine methyl ester hydro­chloride: an intermediate in the synthesis of valsartan

The title compound {systematic name: methyl 2-[(2'-cyano­bi­phenyl-4-yl)­methyl­ammonio]-3-methyl­butanoate chloride}, C₂₀H₂₃N₂O₂⁺·Cl^-, is a key intermediate in the synthesis of valsartan. It crystallizes with two ion pairs in the asymmetric unit, related pseudocentrosymmetrically to each other. The two cations differ only in the orientation of the iso­propyl group.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.029
• wR factor = 0.068
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         88 PerFit
PLAT113_ALERT_2_B ADDSYM Suggests Possible Pseudo/New Spacegroup .      P21/c

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3A    -   C4A     ..       5.72 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C22    -   C27    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C22A   -   C27A   ...       1.44 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         41
            C23 -C22 -C27 -N27    11.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         42
            C21 -C22 -C27 -N27  -165.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         83
            C23A-C22A-C27A-N27A   -4.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         84
            C21A-C22A-C27A-N27A  173.00  3.00   1.555   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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           27.42
           From the CIF: _reflns_number_total               8739
           Count of symmetry unique reflns         4768
           Completeness (_total/calc)            183.28%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3971
           Fraction of Friedel pairs measured     0.833
           Are heavy atom types Z>Si present          yes

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

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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).

methyl 2-[(2'-cyanobiphenyl-4-yl)methylammonio]-3-methylbutanoate chloride

Crystal data

C20H23N2O2^+·Cl^−	F(000) = 760
Mr = 358.85	Dx = 1.232 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 43202 reflections
a = 15.6095 (8) Å	θ = 2.6–27.3°
b = 6.8297 (4) Å	µ = 0.21 mm^−1
c = 18.6854 (9) Å	T = 173 K
β = 103.739 (4)°	Plate, colourless
V = 1935.02 (18) Å^3	0.33 × 0.27 × 0.19 mm
Z = 4

Data collection

STOE IPDS II two-circle diffractometer	8739 independent reflections
Radiation source: fine-focus sealed tube	7170 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
ω scans	θmax = 27.4°, θmin = 2.7°
Absorption correction: multi-scan (MULABS; Spek, 1990; Blessing, 1995)	h = −20→20
Tmin = 0.871, Tmax = 0.981	k = −8→8
56436 measured reflections	l = −22→24

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.068	w = 1/[σ^2(Fo^2) + (0.0376P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.90	(Δ/σ)max = 0.001
8739 reflections	Δρmax = 0.14 e Å^−3
467 parameters	Δρmin = −0.21 e Å^−3
1 restraint	Absolute structure: 3990 Friedel pairs, Flack H. D. (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (3)

Special details

Experimental. Elemental analysis was carried out using Vario EL III CHN-OS elemental analyser

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
Cl1	0.46000 (3)	0.64149 (5)	0.42837 (2)	0.04043 (10)
C1	0.60157 (10)	0.6467 (3)	0.60922 (8)	0.0344 (3)
H1A	0.6292	0.5685	0.5761	0.041*
H1B	0.6024	0.7855	0.5942	0.041*
N2	0.50693 (8)	0.5823 (2)	0.59880 (7)	0.0325 (3)
H2A	0.5070 (14)	0.450 (3)	0.6033 (11)	0.053 (6)*
H2B	0.4788 (12)	0.607 (3)	0.5505 (11)	0.041 (5)*
C3	0.45804 (11)	0.6761 (2)	0.64993 (8)	0.0375 (4)
H3	0.4811	0.8124	0.6602	0.045*
C31	0.35758 (11)	0.6899 (3)	0.61595 (10)	0.0457 (4)
H31	0.3295	0.7309	0.6564	0.055*
C32	0.33606 (13)	0.8467 (3)	0.55697 (12)	0.0557 (5)
H32A	0.3623	0.9712	0.5771	0.084*
H32B	0.2719	0.8614	0.5406	0.084*
H32C	0.3600	0.8087	0.5151	0.084*
C33	0.31803 (13)	0.4941 (3)	0.58815 (13)	0.0610 (5)
H33A	0.3328	0.3973	0.6279	0.092*
H33B	0.3418	0.4516	0.5467	0.092*
H33C	0.2538	0.5067	0.5719	0.092*
C4	0.47319 (11)	0.5694 (3)	0.72256 (9)	0.0420 (4)
O41	0.48967 (8)	0.38078 (17)	0.71526 (6)	0.0449 (3)
C41	0.50258 (14)	0.2607 (3)	0.78061 (10)	0.0590 (5)
H41A	0.5141	0.1253	0.7683	0.088*
H41B	0.4495	0.2651	0.7999	0.088*
H41C	0.5530	0.3103	0.8180	0.088*
O42	0.46480 (10)	0.6476 (3)	0.77756 (7)	0.0640 (4)
C11	0.65634 (10)	0.6262 (2)	0.68679 (8)	0.0314 (3)
C12	0.67327 (11)	0.7870 (2)	0.73320 (9)	0.0373 (3)
H12	0.6484	0.9104	0.7163	0.045*
C13	0.72605 (11)	0.7704 (2)	0.80391 (9)	0.0373 (4)
H13	0.7365	0.8823	0.8350	0.045*
C14	0.76397 (10)	0.5923 (2)	0.83005 (9)	0.0341 (3)
C15	0.74818 (11)	0.4307 (3)	0.78286 (9)	0.0357 (3)
H15	0.7746	0.3083	0.7991	0.043*
C16	0.69484 (11)	0.4472 (2)	0.71310 (9)	0.0342 (3)
H16	0.6839	0.3350	0.6822	0.041*
C21	0.81981 (11)	0.5780 (2)	0.90632 (9)	0.0364 (3)
C22	0.81281 (11)	0.4232 (3)	0.95412 (9)	0.0375 (3)
C23	0.86363 (12)	0.4177 (3)	1.02620 (9)	0.0431 (4)
H23	0.8577	0.3116	1.0575	0.052*
C24	0.92239 (12)	0.5656 (3)	1.05212 (10)	0.0471 (4)
H24	0.9567	0.5627	1.1014	0.057*
C25	0.93129 (12)	0.7182 (3)	1.00630 (10)	0.0493 (4)
H25	0.9724	0.8198	1.0241	0.059*
C26	0.88083 (11)	0.7253 (3)	0.93444 (9)	0.0436 (4)
H26	0.8878	0.8321	0.9037	0.052*
C27	0.74803 (12)	0.2712 (2)	0.93125 (9)	0.0402 (4)
N27	0.69670 (12)	0.1489 (2)	0.91460 (9)	0.0526 (4)
Cl1A	0.95713 (3)	−0.06928 (5)	0.42820 (2)	0.04269 (10)
C1A	0.88459 (11)	0.4322 (3)	0.39888 (9)	0.0352 (3)
H1A1	0.8846	0.5562	0.4263	0.042*
H1A2	0.8555	0.3315	0.4231	0.042*
N2A	0.97833 (8)	0.37139 (19)	0.40492 (7)	0.0310 (3)
H2C	0.9810 (13)	0.232 (3)	0.3977 (10)	0.048 (5)*
H2D	1.0067 (12)	0.387 (2)	0.4525 (10)	0.036 (4)*
C3A	1.02892 (11)	0.4824 (2)	0.35974 (8)	0.0346 (3)
H3A	1.0055	0.6192	0.3532	0.042*
C31A	1.12703 (12)	0.4906 (3)	0.40162 (10)	0.0450 (4)
H31A	1.1289	0.5423	0.4520	0.054*
C32A	1.17824 (15)	0.6339 (4)	0.36527 (12)	0.0715 (6)
H32D	1.1487	0.7615	0.3599	0.107*
H32E	1.1808	0.5843	0.3166	0.107*
H32F	1.2383	0.6482	0.3959	0.107*
C33A	1.17081 (12)	0.2889 (4)	0.41145 (12)	0.0591 (5)
H33D	1.1367	0.2006	0.4355	0.089*
H33E	1.2310	0.3009	0.4421	0.089*
H33F	1.1728	0.2358	0.3631	0.089*
C4A	1.01912 (10)	0.3914 (3)	0.28449 (8)	0.0402 (4)
O41A	1.00829 (8)	0.19806 (17)	0.28657 (6)	0.0422 (3)
C41A	1.00293 (14)	0.0910 (4)	0.21888 (11)	0.0619 (5)
H41D	0.9948	−0.0486	0.2274	0.093*
H41E	1.0575	0.1098	0.2025	0.093*
H41F	0.9528	0.1394	0.1809	0.093*
O42A	1.02639 (10)	0.4820 (2)	0.23129 (7)	0.0600 (4)
C11A	0.83081 (10)	0.4609 (2)	0.32136 (9)	0.0336 (3)
C12A	0.80834 (10)	0.3040 (2)	0.27272 (9)	0.0366 (3)
H12A	0.8278	0.1755	0.2881	0.044*
C13A	0.75787 (11)	0.3354 (3)	0.20230 (9)	0.0385 (4)
H13A	0.7436	0.2278	0.1694	0.046*
C14A	0.72740 (10)	0.5220 (2)	0.17841 (9)	0.0351 (3)
C15A	0.74858 (11)	0.6767 (2)	0.22772 (9)	0.0389 (4)
H15A	0.7276	0.8046	0.2130	0.047*
C16A	0.80003 (11)	0.6462 (3)	0.29807 (9)	0.0377 (3)
H16A	0.8145	0.7539	0.3309	0.045*
C21A	0.67499 (11)	0.5491 (2)	0.10145 (9)	0.0367 (3)
C22A	0.68915 (11)	0.7055 (2)	0.05681 (9)	0.0364 (3)
C23A	0.64110 (11)	0.7222 (3)	−0.01645 (9)	0.0407 (4)
H23A	0.6510	0.8297	−0.0457	0.049*
C24A	0.57941 (12)	0.5819 (3)	−0.04581 (10)	0.0444 (4)
H24A	0.5472	0.5916	−0.0957	0.053*
C25A	0.56438 (12)	0.4275 (3)	−0.00303 (10)	0.0465 (4)
H25A	0.5219	0.3310	−0.0237	0.056*
C26A	0.61069 (12)	0.4117 (3)	0.06988 (9)	0.0436 (4)
H26A	0.5985	0.3057	0.0989	0.052*
C27A	0.75617 (12)	0.8517 (2)	0.08259 (9)	0.0400 (4)
N27A	0.80821 (12)	0.9709 (2)	0.09955 (9)	0.0529 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0550 (2)	0.03156 (18)	0.0319 (2)	0.00088 (17)	0.00472 (17)	0.00091 (16)
C1	0.0394 (8)	0.0331 (7)	0.0307 (7)	−0.0016 (7)	0.0080 (6)	0.0011 (6)
N2	0.0333 (7)	0.0349 (7)	0.0270 (6)	0.0008 (5)	0.0027 (5)	−0.0004 (5)
C3	0.0353 (8)	0.0417 (9)	0.0347 (8)	0.0023 (6)	0.0071 (6)	−0.0048 (6)
C31	0.0350 (8)	0.0610 (11)	0.0415 (9)	0.0084 (7)	0.0101 (7)	0.0065 (8)
C32	0.0391 (9)	0.0672 (12)	0.0621 (12)	0.0149 (9)	0.0145 (9)	0.0157 (10)
C33	0.0378 (10)	0.0770 (14)	0.0633 (13)	−0.0121 (9)	0.0022 (9)	0.0133 (10)
C4	0.0325 (8)	0.0602 (10)	0.0319 (8)	0.0041 (7)	0.0048 (6)	−0.0035 (7)
O41	0.0499 (7)	0.0516 (7)	0.0327 (6)	−0.0011 (5)	0.0091 (5)	0.0041 (5)
C41	0.0612 (12)	0.0723 (14)	0.0421 (10)	−0.0012 (10)	0.0097 (9)	0.0170 (9)
O42	0.0734 (9)	0.0867 (10)	0.0311 (6)	0.0261 (8)	0.0105 (6)	−0.0055 (7)
C11	0.0293 (7)	0.0343 (7)	0.0306 (7)	−0.0019 (6)	0.0070 (6)	0.0000 (6)
C12	0.0411 (8)	0.0307 (7)	0.0388 (8)	0.0003 (6)	0.0071 (7)	0.0009 (6)
C13	0.0431 (9)	0.0319 (8)	0.0357 (8)	−0.0038 (6)	0.0070 (7)	−0.0047 (6)
C14	0.0320 (8)	0.0390 (8)	0.0320 (8)	−0.0008 (6)	0.0091 (6)	−0.0032 (6)
C15	0.0368 (8)	0.0349 (7)	0.0347 (8)	0.0051 (7)	0.0070 (6)	0.0009 (7)
C16	0.0360 (8)	0.0316 (8)	0.0349 (8)	0.0020 (6)	0.0083 (6)	−0.0032 (6)
C21	0.0344 (8)	0.0430 (8)	0.0321 (8)	0.0035 (7)	0.0087 (6)	−0.0021 (6)
C22	0.0370 (8)	0.0405 (8)	0.0359 (8)	0.0065 (7)	0.0106 (6)	−0.0021 (7)
C23	0.0445 (9)	0.0491 (9)	0.0357 (8)	0.0105 (8)	0.0093 (7)	0.0044 (8)
C24	0.0417 (10)	0.0647 (11)	0.0318 (8)	0.0071 (8)	0.0024 (7)	−0.0027 (8)
C25	0.0425 (9)	0.0634 (11)	0.0393 (9)	−0.0064 (9)	0.0042 (8)	−0.0078 (8)
C26	0.0408 (9)	0.0525 (10)	0.0361 (8)	−0.0050 (8)	0.0064 (7)	−0.0003 (7)
C27	0.0502 (9)	0.0361 (8)	0.0342 (8)	0.0077 (8)	0.0101 (7)	0.0037 (6)
N27	0.0680 (11)	0.0401 (8)	0.0485 (8)	−0.0042 (8)	0.0114 (8)	0.0025 (7)
Cl1A	0.0619 (3)	0.03245 (19)	0.0297 (2)	−0.00554 (18)	0.00287 (18)	−0.00058 (16)
C1A	0.0328 (8)	0.0391 (8)	0.0339 (8)	−0.0008 (7)	0.0082 (6)	−0.0003 (7)
N2A	0.0318 (6)	0.0333 (7)	0.0270 (6)	−0.0023 (5)	0.0050 (5)	0.0004 (5)
C3A	0.0347 (8)	0.0379 (8)	0.0313 (7)	−0.0044 (6)	0.0081 (6)	0.0024 (6)
C31A	0.0371 (9)	0.0615 (10)	0.0362 (8)	−0.0152 (8)	0.0082 (7)	−0.0042 (7)
C32A	0.0586 (12)	0.0999 (17)	0.0568 (12)	−0.0421 (13)	0.0150 (10)	0.0014 (12)
C33A	0.0332 (9)	0.0852 (15)	0.0552 (11)	0.0053 (10)	0.0032 (8)	−0.0038 (11)
C4A	0.0314 (8)	0.0565 (10)	0.0316 (8)	−0.0042 (7)	0.0051 (6)	0.0061 (7)
O41A	0.0445 (6)	0.0512 (7)	0.0316 (5)	−0.0019 (5)	0.0105 (5)	−0.0062 (5)
C41A	0.0603 (12)	0.0835 (15)	0.0426 (10)	−0.0070 (10)	0.0137 (9)	−0.0241 (10)
O42A	0.0674 (9)	0.0801 (10)	0.0319 (7)	−0.0150 (7)	0.0103 (7)	0.0102 (6)
C11A	0.0288 (7)	0.0386 (8)	0.0339 (8)	−0.0010 (6)	0.0085 (6)	−0.0039 (6)
C12A	0.0352 (8)	0.0340 (8)	0.0401 (8)	−0.0022 (7)	0.0082 (7)	−0.0025 (7)
C13A	0.0378 (8)	0.0385 (8)	0.0383 (8)	−0.0052 (7)	0.0072 (7)	−0.0074 (7)
C14A	0.0307 (8)	0.0396 (8)	0.0347 (8)	0.0001 (6)	0.0072 (7)	−0.0042 (6)
C15A	0.0389 (9)	0.0364 (9)	0.0391 (8)	0.0053 (6)	0.0050 (7)	−0.0046 (6)
C16A	0.0378 (8)	0.0378 (8)	0.0356 (8)	0.0017 (7)	0.0047 (7)	−0.0089 (7)
C21A	0.0337 (8)	0.0410 (8)	0.0347 (8)	0.0000 (7)	0.0066 (7)	−0.0053 (7)
C22A	0.0350 (8)	0.0379 (8)	0.0361 (8)	0.0026 (6)	0.0083 (7)	−0.0059 (7)
C23A	0.0412 (9)	0.0423 (8)	0.0385 (8)	0.0038 (7)	0.0094 (7)	−0.0021 (7)
C24A	0.0432 (10)	0.0551 (10)	0.0330 (8)	0.0035 (8)	0.0055 (7)	−0.0027 (7)
C25A	0.0404 (9)	0.0565 (10)	0.0389 (8)	−0.0100 (8)	0.0021 (7)	−0.0073 (8)
C26A	0.0427 (9)	0.0495 (9)	0.0372 (8)	−0.0077 (8)	0.0067 (7)	−0.0012 (7)
C27A	0.0441 (9)	0.0371 (8)	0.0385 (8)	0.0027 (7)	0.0093 (7)	−0.0047 (7)
N27A	0.0584 (10)	0.0458 (9)	0.0531 (9)	−0.0074 (7)	0.0106 (8)	−0.0087 (7)

Geometric parameters (Å, º)

C1—C11	1.504 (2)	C1A—N2A	1.499 (2)
C1—N2	1.509 (2)	C1A—C11A	1.505 (2)
C1—H1A	0.9900	C1A—H1A1	0.9900
C1—H1B	0.9900	C1A—H1A2	0.9900
N2—C3	1.5005 (19)	N2A—C3A	1.4926 (19)
N2—H2A	0.91 (2)	N2A—H2C	0.96 (2)
N2—H2B	0.920 (19)	N2A—H2D	0.901 (19)
C3—C4	1.509 (2)	C3A—C4A	1.512 (2)
C3—C31	1.549 (2)	C3A—C31A	1.546 (2)
C3—H3	1.0000	C3A—H3A	1.0000
C31—C33	1.512 (3)	C31A—C32A	1.522 (3)
C31—C32	1.516 (3)	C31A—C33A	1.529 (3)
C31—H31	1.0000	C31A—H31A	1.0000
C32—H32A	0.9800	C32A—H32D	0.9800
C32—H32B	0.9800	C32A—H32E	0.9800
C32—H32C	0.9800	C32A—H32F	0.9800
C33—H33A	0.9800	C33A—H33D	0.9800
C33—H33B	0.9800	C33A—H33E	0.9800
C33—H33C	0.9800	C33A—H33F	0.9800
C4—O42	1.193 (2)	C4A—O42A	1.199 (2)
C4—O41	1.327 (2)	C4A—O41A	1.333 (2)
O41—C41	1.445 (2)	O41A—C41A	1.446 (2)
C41—H41A	0.9800	C41A—H41D	0.9800
C41—H41B	0.9800	C41A—H41E	0.9800
C41—H41C	0.9800	C41A—H41F	0.9800
C11—C12	1.386 (2)	C11A—C16A	1.387 (2)
C11—C16	1.399 (2)	C11A—C12A	1.395 (2)
C12—C13	1.386 (2)	C12A—C13A	1.380 (2)
C12—H12	0.9500	C12A—H12A	0.9500
C13—C14	1.390 (2)	C13A—C14A	1.396 (2)
C13—H13	0.9500	C13A—H13A	0.9500
C14—C15	1.398 (2)	C14A—C15A	1.390 (2)
C14—C21	1.487 (2)	C14A—C21A	1.488 (2)
C15—C16	1.374 (2)	C15A—C16A	1.384 (2)
C15—H15	0.9500	C15A—H15A	0.9500
C16—H16	0.9500	C16A—H16A	0.9500
C21—C26	1.399 (2)	C21A—C26A	1.398 (2)
C21—C22	1.405 (2)	C21A—C22A	1.405 (2)
C22—C23	1.392 (2)	C22A—C23A	1.401 (2)
C22—C27	1.441 (3)	C22A—C27A	1.444 (2)
C23—C24	1.373 (3)	C23A—C24A	1.377 (3)
C23—H23	0.9500	C23A—H23A	0.9500
C24—C25	1.377 (3)	C24A—C25A	1.376 (3)
C24—H24	0.9500	C24A—H24A	0.9500
C25—C26	1.387 (2)	C25A—C26A	1.387 (2)
C25—H25	0.9500	C25A—H25A	0.9500
C26—H26	0.9500	C26A—H26A	0.9500
C27—N27	1.148 (2)	C27A—N27A	1.140 (2)
C11—C1—N2	114.34 (12)	N2A—C1A—C11A	114.83 (13)
C11—C1—H1A	108.7	N2A—C1A—H1A1	108.6
N2—C1—H1A	108.7	C11A—C1A—H1A1	108.6
C11—C1—H1B	108.7	N2A—C1A—H1A2	108.6
N2—C1—H1B	108.7	C11A—C1A—H1A2	108.6
H1A—C1—H1B	107.6	H1A1—C1A—H1A2	107.5
C3—N2—C1	115.09 (12)	C3A—N2A—C1A	117.04 (12)
C3—N2—H2A	110.8 (13)	C3A—N2A—H2C	112.1 (12)
C1—N2—H2A	107.3 (14)	C1A—N2A—H2C	109.7 (12)
C3—N2—H2B	110.5 (11)	C3A—N2A—H2D	107.1 (11)
C1—N2—H2B	107.4 (11)	C1A—N2A—H2D	106.4 (11)
H2A—N2—H2B	105.1 (17)	H2C—N2A—H2D	103.4 (16)
N2—C3—C4	111.82 (13)	N2A—C3A—C4A	111.52 (13)
N2—C3—C31	112.55 (13)	N2A—C3A—C31A	108.99 (12)
C4—C3—C31	108.99 (13)	C4A—C3A—C31A	110.78 (13)
N2—C3—H3	107.8	N2A—C3A—H3A	108.5
C4—C3—H3	107.8	C4A—C3A—H3A	108.5
C31—C3—H3	107.8	C31A—C3A—H3A	108.5
C33—C31—C32	111.89 (16)	C32A—C31A—C33A	111.45 (18)
C33—C31—C3	112.21 (15)	C32A—C31A—C3A	111.05 (15)
C32—C31—C3	111.66 (15)	C33A—C31A—C3A	112.89 (14)
C33—C31—H31	106.9	C32A—C31A—H31A	107.0
C32—C31—H31	106.9	C33A—C31A—H31A	107.0
C3—C31—H31	106.9	C3A—C31A—H31A	107.0
C31—C32—H32A	109.5	C31A—C32A—H32D	109.5
C31—C32—H32B	109.5	C31A—C32A—H32E	109.5
H32A—C32—H32B	109.5	H32D—C32A—H32E	109.5
C31—C32—H32C	109.5	C31A—C32A—H32F	109.5
H32A—C32—H32C	109.5	H32D—C32A—H32F	109.5
H32B—C32—H32C	109.5	H32E—C32A—H32F	109.5
C31—C33—H33A	109.5	C31A—C33A—H33D	109.5
C31—C33—H33B	109.5	C31A—C33A—H33E	109.5
H33A—C33—H33B	109.5	H33D—C33A—H33E	109.5
C31—C33—H33C	109.5	C31A—C33A—H33F	109.5
H33A—C33—H33C	109.5	H33D—C33A—H33F	109.5
H33B—C33—H33C	109.5	H33E—C33A—H33F	109.5
O42—C4—O41	125.94 (17)	O42A—C4A—O41A	124.96 (17)
O42—C4—C3	122.19 (17)	O42A—C4A—C3A	123.39 (17)
O41—C4—C3	111.68 (13)	O41A—C4A—C3A	111.47 (13)
C4—O41—C41	117.10 (14)	C4A—O41A—C41A	117.17 (15)
O41—C41—H41A	109.5	O41A—C41A—H41D	109.5
O41—C41—H41B	109.5	O41A—C41A—H41E	109.5
H41A—C41—H41B	109.5	H41D—C41A—H41E	109.5
O41—C41—H41C	109.5	O41A—C41A—H41F	109.5
H41A—C41—H41C	109.5	H41D—C41A—H41F	109.5
H41B—C41—H41C	109.5	H41E—C41A—H41F	109.5
C12—C11—C16	118.08 (14)	C16A—C11A—C12A	118.81 (15)
C12—C11—C1	120.64 (15)	C16A—C11A—C1A	119.56 (14)
C16—C11—C1	121.22 (15)	C12A—C11A—C1A	121.59 (15)
C11—C12—C13	120.89 (15)	C13A—C12A—C11A	120.00 (16)
C11—C12—H12	119.6	C13A—C12A—H12A	120.0
C13—C12—H12	119.6	C11A—C12A—H12A	120.0
C12—C13—C14	120.94 (15)	C12A—C13A—C14A	121.37 (15)
C12—C13—H13	119.5	C12A—C13A—H13A	119.3
C14—C13—H13	119.5	C14A—C13A—H13A	119.3
C13—C14—C15	118.21 (15)	C15A—C14A—C13A	118.24 (15)
C13—C14—C21	119.90 (14)	C15A—C14A—C21A	122.39 (15)
C15—C14—C21	121.89 (15)	C13A—C14A—C21A	119.37 (14)
C16—C15—C14	120.67 (16)	C16A—C15A—C14A	120.54 (16)
C16—C15—H15	119.7	C16A—C15A—H15A	119.7
C14—C15—H15	119.7	C14A—C15A—H15A	119.7
C15—C16—C11	121.18 (15)	C15A—C16A—C11A	121.01 (15)
C15—C16—H16	119.4	C15A—C16A—H16A	119.5
C11—C16—H16	119.4	C11A—C16A—H16A	119.5
C26—C21—C22	116.82 (15)	C26A—C21A—C22A	117.28 (15)
C26—C21—C14	120.28 (15)	C26A—C21A—C14A	119.92 (16)
C22—C21—C14	122.86 (15)	C22A—C21A—C14A	122.75 (15)
C23—C22—C21	121.52 (17)	C23A—C22A—C21A	121.26 (15)
C23—C22—C27	117.80 (16)	C23A—C22A—C27A	116.57 (15)
C21—C22—C27	120.56 (15)	C21A—C22A—C27A	122.11 (15)
C24—C23—C22	120.09 (18)	C24A—C23A—C22A	119.63 (17)
C24—C23—H23	120.0	C24A—C23A—H23A	120.2
C22—C23—H23	120.0	C22A—C23A—H23A	120.2
C23—C24—C25	119.68 (17)	C25A—C24A—C23A	120.08 (17)
C23—C24—H24	120.2	C25A—C24A—H24A	120.0
C25—C24—H24	120.2	C23A—C24A—H24A	120.0
C24—C25—C26	120.71 (18)	C24A—C25A—C26A	120.63 (17)
C24—C25—H25	119.6	C24A—C25A—H25A	119.7
C26—C25—H25	119.6	C26A—C25A—H25A	119.7
C25—C26—C21	121.18 (18)	C25A—C26A—C21A	121.10 (17)
C25—C26—H26	119.4	C25A—C26A—H26A	119.5
C21—C26—H26	119.4	C21A—C26A—H26A	119.5
N27—C27—C22	178.51 (18)	N27A—C27A—C22A	176.66 (19)
C11—C1—N2—C3	53.57 (18)	C1A—N2A—C3A—C4A	−89.72 (17)
C1—N2—C3—C4	−85.06 (16)	C1A—N2A—C3A—C31A	147.67 (14)
C1—N2—C3—C31	151.87 (14)	N2A—C3A—C31A—C32A	−169.18 (17)
N2—C3—C31—C33	53.11 (19)	C4A—C3A—C31A—C32A	67.8 (2)
C4—C3—C31—C33	−71.53 (19)	N2A—C3A—C31A—C33A	64.81 (18)
N2—C3—C31—C32	−73.44 (19)	C4A—C3A—C31A—C33A	−58.25 (19)
C4—C3—C31—C32	161.91 (16)	N2A—C3A—C4A—O42A	153.67 (16)
N2—C3—C4—O42	156.10 (16)	C31A—C3A—C4A—O42A	−84.7 (2)
C31—C3—C4—O42	−78.8 (2)	N2A—C3A—C4A—O41A	−31.03 (18)
N2—C3—C4—O41	−28.61 (19)	C31A—C3A—C4A—O41A	90.55 (16)
C31—C3—C4—O41	96.46 (16)	O42A—C4A—O41A—C41A	−1.5 (3)
O42—C4—O41—C41	−3.0 (3)	C3A—C4A—O41A—C41A	−176.70 (14)
C3—C4—O41—C41	−178.07 (14)	N2A—C1A—C11A—C16A	−114.59 (17)
N2—C1—C11—C12	−100.07 (17)	N2A—C1A—C11A—C12A	67.7 (2)
N2—C1—C11—C16	82.85 (18)	C16A—C11A—C12A—C13A	1.3 (2)
C16—C11—C12—C13	−0.7 (2)	C1A—C11A—C12A—C13A	179.11 (15)
C1—C11—C12—C13	−177.88 (16)	C11A—C12A—C13A—C14A	−0.8 (2)
C11—C12—C13—C14	0.5 (3)	C12A—C13A—C14A—C15A	−0.5 (2)
C12—C13—C14—C15	0.6 (2)	C12A—C13A—C14A—C21A	178.58 (15)
C12—C13—C14—C21	−179.55 (15)	C13A—C14A—C15A—C16A	1.3 (2)
C13—C14—C15—C16	−1.5 (2)	C21A—C14A—C15A—C16A	−177.79 (16)
C21—C14—C15—C16	178.68 (15)	C14A—C15A—C16A—C11A	−0.7 (3)
C14—C15—C16—C11	1.3 (2)	C12A—C11A—C16A—C15A	−0.6 (2)
C12—C11—C16—C15	−0.2 (2)	C1A—C11A—C16A—C15A	−178.40 (15)
C1—C11—C16—C15	176.98 (15)	C15A—C14A—C21A—C26A	−139.58 (17)
C13—C14—C21—C26	−42.3 (2)	C13A—C14A—C21A—C26A	41.4 (2)
C15—C14—C21—C26	137.52 (17)	C15A—C14A—C21A—C22A	42.8 (2)
C13—C14—C21—C22	135.64 (16)	C13A—C14A—C21A—C22A	−136.20 (17)
C15—C14—C21—C22	−44.5 (2)	C26A—C21A—C22A—C23A	−0.3 (2)
C26—C21—C22—C23	0.5 (2)	C14A—C21A—C22A—C23A	177.30 (15)
C14—C21—C22—C23	−177.47 (15)	C26A—C21A—C22A—C27A	−177.51 (15)
C26—C21—C22—C27	176.30 (15)	C14A—C21A—C22A—C27A	0.1 (2)
C14—C21—C22—C27	−1.7 (2)	C21A—C22A—C23A—C24A	−0.7 (3)
C21—C22—C23—C24	−0.1 (3)	C27A—C22A—C23A—C24A	176.58 (15)
C27—C22—C23—C24	−175.94 (16)	C22A—C23A—C24A—C25A	0.8 (3)
C22—C23—C24—C25	−0.6 (3)	C23A—C24A—C25A—C26A	0.2 (3)
C23—C24—C25—C26	0.7 (3)	C24A—C25A—C26A—C21A	−1.3 (3)
C24—C25—C26—C21	−0.2 (3)	C22A—C21A—C26A—C25A	1.4 (3)
C22—C21—C26—C25	−0.4 (3)	C14A—C21A—C26A—C25A	−176.33 (16)
C14—C21—C26—C25	177.67 (17)	C23A—C22A—C27A—N27A	−4 (3)
C23—C22—C27—N27	11 (7)	C21A—C22A—C27A—N27A	173 (3)
C21—C22—C27—N27	−165 (7)	N2—C3—C31—H31	169.99
C11A—C1A—N2A—C3A	46.89 (19)	N2A—C3A—C31A—H31A	−52.69

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···Cl1	0.920 (19)	2.243 (19)	3.1199 (13)	159.0 (15)
N2—H2A···Cl1^i	0.91 (2)	2.28 (2)	3.1168 (14)	153.1 (18)
N2A—H2C···Cl1A	0.96 (2)	2.19 (2)	3.0700 (14)	151.1 (16)
N2A—H2D···Cl1A^ii	0.901 (19)	2.185 (19)	3.0676 (14)	166.0 (15)

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+2, y+1/2, −z+1.