4-Cyano-N-ethyl-spiro-[chromene-2,4'-piperidine]-1'-carboxamide.

The title compound, C17H19N3O2, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. In both mol-ecules, the pyran ring has a twisted conformation ((5)S4), with Q = 0.301 (3) Å, θ = 116.7 (6) and ϕ= 213.6 (7)° for mol-ecule A, and Q = 0.364 (2) Å, θ = 113.7 (3) and ϕ = 213.0 (4)° for mol-ecule B. In mol-ecule B, the terminal ethyl group is disordered over two orientations with an occupancy ratio of 0.55 (1):0.45 (1). In the crystal, mol-ecules A and B form very similar but separate R1(2)(7) motifs through N-H⋯O and C-H⋯O hydrogen bonds. The resulting chains along [001] are inter-linked by weaker C-H⋯O and C-H⋯π inter-actions, forming layers parallel to the bc plane.

Related literature

For related structures, see: Rajalakshmi et al. (2012 ▶). For their biological activity, see: Kemnitzer et al. (2004 ▶); Mahdavi et al. (2011 ▶); Patil et al. (2012 ▶); Vosooghi et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H19N3O2

M = 297.35

Monoclinic,

a = 22.7845 (8) Å

b = 14.3370 (5) Å

c = 9.8442 (3) Å

β = 90.783 (1)°

V = 3215.42 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.972, T max = 0.980

26353 measured reflections

5377 independent reflections

3664 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.177

S = 1.04

5377 reflections

455 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLUTON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051124/ld2085sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051124/ld2085Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051124/ld2085Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H19N3O2	F(000) = 1264
Mr = 297.35	Dx = 1.228 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5377 reflections
a = 22.7845 (8) Å	θ = 2–24.5°
b = 14.3370 (5) Å	µ = 0.08 mm−1
c = 9.8442 (3) Å	T = 298 K
β = 90.783 (1)°	Block, colourless
V = 3215.42 (19) Å3	0.35 × 0.30 × 0.25 mm
Z = 8

Bruker Kappa APEXII diffractometer	5377 independent reflections
Radiation source: fine-focus sealed tube	3664 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 24.5°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −26→26
Tmin = 0.972, Tmax = 0.980	k = −16→16
26353 measured reflections	l = −11→11

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0985P)2 + 0.7688P] where P = (Fo2 + 2Fc2)/3
5377 reflections	(Δ/σ)max < 0.001
455 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 21.7749 (0.0093) x - 3.7501 (0.0221) y + 1.2007 (0.0105) z = 19.0074 (0.0242) * 0.0040 (0.0012) C10B * -0.0040 (0.0012) C11B * 0.0040 (0.0012) C12B * -0.0040 (0.0012) C13B 0.6065 (0.0031) N2B -0.6644 (0.0031) C1B Rms deviation of fitted atoms = 0.0040 - 7.4187 (0.0441) x + 12.7666 (0.0128) y + 3.1729 (0.0124) z = 1.9928 (0.0318) Angle to previous plane (with approximate esd) = 59.92 ( 0.15 ) * -0.0108 (0.0016) C10A * 0.0109 (0.0016) C11A * -0.0109 (0.0016) C12A * 0.0108 (0.0016) C13A -0.6263 (0.0038) N2A 0.6418 (0.0039) C1A Rms deviation of fitted atoms = 0.0109 4.5322 (0.0409) x - 8.3873 (0.0214) y + 7.7125 (0.0087) z = 2.7977 (0.0417) Angle to previous plane (with approximate esd) = 70.38 ( 0.11 ) * 0.0378 (0.0016) C7A * 0.0217 (0.0009) C9A * -0.0402 (0.0017) C8A * -0.0193 (0.0008) C2A 0.2626 (0.0051) C1A -0.1926 (0.0048) O1A Rms deviation of fitted atoms = 0.0312 5.5265 (0.0340) x - 2.7276 (0.0239) y + 9.3313 (0.0033) z = 11.8513 (0.0329) Angle to previous plane (with approximate esd) = 24.84 ( 0.15 ) * 0.0573 (0.0014) C7B * 0.0322 (0.0008) C9B * -0.0600 (0.0015) C8B * -0.0295 (0.0007) C2B 0.3063 (0.0047) C1B -0.2375 (0.0041) O1B Rms deviation of fitted atoms = 0.0469 13.1321 (0.0221) x - 10.5040 (0.0116) y - 3.6406 (0.0129) z = 2.2898 (0.0197) Angle to previous plane (with approximate esd) = 86.26 ( 0.11 ) * 0.2282 (0.0021) C10A * -0.2326 (0.0021) C11A * -0.2132 (0.0023) C12A * 0.2074 (0.0023) C13A * 0.2229 (0.0020) N2A * -0.2128 (0.0019) C1A Rms deviation of fitted atoms = 0.2197 16.1311 (0.0326) x - 9.6533 (0.0246) y - 2.1927 (0.0143) z = 5.2730 (0.0209) Angle to previous plane (with approximate esd) = 11.90 ( 0.24 ) * 0.0010 (0.0008) O2A * -0.0020 (0.0016) C14A * 0.0019 (0.0015) N3A * -0.0009 (0.0007) C15A Rms deviation of fitted atoms = 0.0015 13.1321 (0.0221) x - 10.5040 (0.0116) y - 3.6406 (0.0129) z = 2.2898 (0.0197) Angle to previous plane (with approximate esd) = 11.90 ( 0.24 ) * 0.2282 (0.0021) C10A * -0.2326 (0.0021) C11A * -0.2132 (0.0023) C12A * 0.2074 (0.0023) C13A * 0.2229 (0.0020) N2A * -0.2128 (0.0019) C1A Rms deviation of fitted atoms = 0.2197 4.0940 (0.0233) x - 7.7943 (0.0130) y + 8.0459 (0.0062) z = 3.0223 (0.0189) Angle to previous plane (with approximate esd) = 78.16 ( 0.09 ) * -0.0636 (0.0019) C9A * 0.1923 (0.0017) C1A * -0.0711 (0.0019) C8A * 0.0861 (0.0018) C7A * 0.0441 (0.0018) C2A * -0.1878 (0.0017) O1A Rms deviation of fitted atoms = 0.1229 19.4554 (0.0116) x - 7.4511 (0.0119) y + 0.1595 (0.0105) z = 13.7691 (0.0188) Angle to previous plane (with approximate esd) = 62.69 ( 0.09 ) * 0.2327 (0.0017) C10B * -0.2207 (0.0017) C11B * -0.2127 (0.0017) C12B * 0.2240 (0.0017) C13B * 0.2129 (0.0017) N2B * -0.2363 (0.0016) C1B Rms deviation of fitted atoms = 0.2234 19.0116 (0.1135) x - 7.7504 (0.1004) y - 1.1689 (0.0356) z = 12.1762 (0.2227) Angle to previous plane (with approximate esd) = 7.92 ( 0.76 ) * 0.0316 (0.0019) O2B * -0.0581 (0.0036) C14B * 0.0512 (0.0032) N3B * -0.0247 (0.0015) C15B_a Rms deviation of fitted atoms = 0.0436 19.4554 (0.0116) x - 7.4511 (0.0119) y + 0.1595 (0.0105) z = 13.7691 (0.0188) Angle to previous plane (with approximate esd) = 7.92 ( 0.76 ) * 0.2327 (0.0017) C10B * -0.2207 (0.0017) C11B * -0.2127 (0.0017) C12B * 0.2240 (0.0017) C13B * 0.2129 (0.0017) N2B * -0.2363 (0.0016) C1B Rms deviation of fitted atoms = 0.2234 4.1399 (0.0218) x - 2.4193 (0.0136) y + 9.5114 (0.0026) z = 11.0331 (0.0176) Angle to previous plane (with approximate esd) = 74.34 ( 0.08 ) * -0.0681 (0.0018) C9B * 0.2285 (0.0016) C1B * -0.0966 (0.0017) C8B * 0.1149 (0.0015) C7B * 0.0475 (0.0015) C2B * -0.2262 (0.0014) O1B Rms deviation of fitted atoms = 0.1488

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.64156 (8)	0.54792 (13)	0.5566 (2)	0.0827 (6)
O2A	0.54458 (9)	0.21606 (13)	0.64983 (17)	0.0765 (5)
N1A	0.86504 (18)	0.6414 (3)	0.5007 (5)	0.1602 (17)
N2A	0.59436 (10)	0.32206 (14)	0.52456 (19)	0.0636 (6)
N3A	0.52207 (10)	0.22847 (16)	0.4292 (2)	0.0679 (6)
C1A	0.67909 (12)	0.47355 (17)	0.5127 (3)	0.0631 (7)
C2A	0.66403 (15)	0.61628 (18)	0.6402 (3)	0.0770 (8)
C3A	0.62636 (19)	0.6657 (2)	0.7180 (3)	0.1049 (11)
H3A	0.5868	0.6498	0.7208	0.126*
C4A	0.6473 (3)	0.7387 (3)	0.7913 (4)	0.1313 (18)
C5A	0.7030 (4)	0.7632 (3)	0.7908 (5)	0.150 (2)
H5A	0.7155	0.8143	0.8418	0.179*
C6A	0.7447 (2)	0.7118 (2)	0.7122 (4)	0.1209 (16)
H6A	0.7843	0.7279	0.7130	0.145*
C7A	0.72431 (15)	0.63792 (17)	0.6358 (3)	0.0767 (9)
C8A	0.75991 (13)	0.5822 (2)	0.5441 (3)	0.0773 (8)
C9A	0.73837 (15)	0.5081 (2)	0.4842 (3)	0.0775 (8)
C10A	0.64728 (14)	0.43474 (18)	0.3889 (3)	0.0733 (8)
H10A	0.6423	0.4842	0.3225	0.088*
H10B	0.6714	0.3866	0.3485	0.088*
C11A	0.58882 (14)	0.3948 (2)	0.4199 (3)	0.0722 (8)
C12A	0.62276 (14)	0.3556 (2)	0.6501 (3)	0.0826 (9)
H12A	0.6278	0.3039	0.7127	0.099*
H12B	0.5978	0.4015	0.6927	0.099*
C13A	0.68102 (13)	0.3981 (2)	0.6220 (3)	0.0744 (8)
H13A	0.7077	0.3493	0.5939	0.089*
H13B	0.6966	0.4250	0.7054	0.089*
C14A	0.55232 (11)	0.25439 (16)	0.5395 (2)	0.0550 (6)
C15A	0.47839 (14)	0.1548 (2)	0.4335 (3)	0.0863 (9)
H15A	0.4797	0.1262	0.5228	0.104*
H15B	0.4398	0.1823	0.4210	0.104*
C16A	0.48610 (19)	0.0829 (3)	0.3323 (5)	0.1428 (18)
H16A	0.4825	0.1098	0.2433	0.214*
H16B	0.4566	0.0358	0.3432	0.214*
H16C	0.5243	0.0554	0.3433	0.214*
C17A	0.81935 (18)	0.6132 (3)	0.5193 (4)	0.1113 (13)
O1B	0.82241 (6)	0.54557 (10)	0.91701 (17)	0.0585 (4)
O2B	1.00094 (7)	0.69692 (11)	1.21492 (17)	0.0658 (5)
N1B	0.78919 (13)	0.18872 (18)	0.8024 (3)	0.1075 (10)
N2B	0.95277 (8)	0.63343 (12)	1.03499 (18)	0.0512 (5)
N3B	1.01500 (10)	0.75979 (14)	1.0100 (3)	0.0654 (6)
C1B	0.87563 (9)	0.48999 (15)	0.9275 (2)	0.0506 (6)
C2B	0.77116 (9)	0.50472 (16)	0.9577 (2)	0.0509 (6)
C3B	0.72738 (11)	0.56214 (19)	1.0024 (3)	0.0669 (7)
H3B	0.7337	0.6260	1.0106	0.080*
C4B	0.67375 (12)	0.5239 (2)	1.0350 (3)	0.0795 (8)
H4B	0.6438	0.5626	1.0645	0.095*
C5B	0.66405 (12)	0.4301 (2)	1.0248 (3)	0.0782 (8)
H5B	0.6279	0.4052	1.0482	0.094*
C6B	0.70809 (11)	0.37264 (19)	0.9795 (2)	0.0649 (7)
H6B	0.7015	0.3088	0.9723	0.078*
C7B	0.76231 (9)	0.40935 (16)	0.9444 (2)	0.0523 (6)
C8B	0.81077 (10)	0.35561 (16)	0.8874 (3)	0.0594 (6)
C9B	0.86373 (11)	0.39305 (17)	0.8769 (3)	0.0617 (7)
C10B	0.91981 (10)	0.54055 (15)	0.8409 (2)	0.0536 (6)
H10C	0.9046	0.5451	0.7486	0.064*
H10D	0.9559	0.5046	0.8387	0.064*
C11B	0.93324 (12)	0.63759 (17)	0.8938 (2)	0.0545 (6)
C12B	0.91192 (11)	0.58582 (17)	1.1254 (2)	0.0606 (6)
H12C	0.8760	0.6218	1.1315	0.073*
H12D	0.9292	0.5815	1.2157	0.073*
C13B	0.89774 (10)	0.48906 (16)	1.0738 (2)	0.0583 (6)
H13C	0.8681	0.4614	1.1309	0.070*
H13D	0.9327	0.4506	1.0802	0.070*
C14B	0.98940 (9)	0.69875 (14)	1.0919 (2)	0.0485 (5)
C15B	1.0460 (8)	0.8346 (14)	1.0830 (13)	0.070 (3)	0.550 (10)
H15C	1.0681	0.8097	1.1597	0.083*	0.550 (10)
H15D	1.0185	0.8808	1.1158	0.083*	0.550 (10)
C16B	1.0868 (4)	0.8769 (6)	0.9786 (7)	0.116 (4)	0.550 (10)
H16D	1.0641	0.9003	0.9031	0.175*	0.550 (10)
H16E	1.1135	0.8300	0.9473	0.175*	0.550 (10)
H16F	1.1086	0.9271	1.0195	0.175*	0.550 (10)
C15C	1.0598 (9)	0.8312 (15)	1.0386 (15)	0.066 (4)	0.450 (10)
H15E	1.0775	0.8203	1.1274	0.079*	0.450 (10)
H15F	1.0905	0.8279	0.9713	0.079*	0.450 (10)
C16C	1.0324 (5)	0.9228 (5)	1.0349 (9)	0.106 (4)	0.450 (10)
H16G	1.0608	0.9694	1.0601	0.159*	0.450 (10)
H16H	1.0005	0.9243	1.0975	0.159*	0.450 (10)
H16I	1.0179	0.9353	0.9448	0.159*	0.450 (10)
C17B	0.79915 (12)	0.2625 (2)	0.8393 (3)	0.0758 (8)
H9A	0.7620 (14)	0.477 (2)	0.420 (4)	0.101 (11)*
H1N3	0.5307 (12)	0.2494 (18)	0.356 (3)	0.066 (8)*
H4A	0.6205 (17)	0.779 (3)	0.852 (4)	0.133 (13)*
H11A	0.5669 (13)	0.455 (2)	0.456 (3)	0.093 (9)*
H11B	0.5679 (12)	0.3651 (18)	0.341 (3)	0.081 (8)*
H2N3	1.0026 (10)	0.7676 (16)	0.932 (3)	0.052 (7)*
H9B	0.8947 (12)	0.3614 (18)	0.840 (3)	0.072 (8)*
H11C	0.9634 (12)	0.6634 (17)	0.839 (3)	0.069 (7)*
H11D	0.8987 (11)	0.6814 (17)	0.889 (2)	0.061 (7)*

	U11	U22	U33	U12	U13	U23
O1A	0.0796 (13)	0.0716 (12)	0.0965 (15)	0.0050 (9)	−0.0153 (10)	−0.0284 (10)
O2A	0.1061 (15)	0.0809 (12)	0.0426 (10)	−0.0100 (10)	0.0012 (9)	0.0106 (8)
N1A	0.112 (3)	0.164 (4)	0.204 (4)	−0.044 (3)	−0.022 (3)	0.075 (3)
N2A	0.0885 (15)	0.0635 (12)	0.0384 (10)	−0.0106 (11)	−0.0159 (10)	0.0057 (9)
N3A	0.0779 (15)	0.0810 (15)	0.0448 (13)	−0.0190 (12)	−0.0040 (11)	0.0060 (11)
C1A	0.0778 (17)	0.0551 (14)	0.0563 (15)	0.0037 (12)	−0.0063 (13)	−0.0072 (11)
C2A	0.118 (3)	0.0527 (15)	0.0595 (16)	0.0125 (16)	−0.0162 (16)	−0.0056 (12)
C3A	0.152 (3)	0.076 (2)	0.087 (2)	0.030 (2)	−0.013 (2)	−0.0171 (18)
C4A	0.235 (6)	0.072 (3)	0.086 (3)	0.027 (3)	−0.034 (3)	−0.025 (2)
C5A	0.295 (8)	0.065 (2)	0.087 (3)	−0.026 (4)	−0.059 (4)	−0.017 (2)
C6A	0.205 (4)	0.071 (2)	0.086 (2)	−0.043 (3)	−0.057 (3)	0.0088 (19)
C7A	0.120 (3)	0.0477 (15)	0.0611 (17)	−0.0121 (15)	−0.0343 (17)	0.0111 (12)
C8A	0.091 (2)	0.0588 (16)	0.081 (2)	−0.0131 (15)	−0.0197 (16)	0.0239 (15)
C9A	0.092 (2)	0.0634 (18)	0.077 (2)	−0.0001 (16)	0.0027 (17)	0.0111 (15)
C10A	0.112 (2)	0.0593 (15)	0.0487 (15)	−0.0092 (15)	−0.0067 (14)	0.0058 (11)
C11A	0.107 (2)	0.0584 (16)	0.0508 (15)	−0.0139 (16)	−0.0289 (15)	0.0066 (12)
C12A	0.099 (2)	0.104 (2)	0.0443 (14)	−0.0282 (17)	−0.0189 (14)	0.0074 (14)
C13A	0.0867 (19)	0.0840 (18)	0.0522 (15)	−0.0136 (15)	−0.0161 (13)	0.0115 (13)
C14A	0.0685 (15)	0.0546 (13)	0.0419 (13)	0.0066 (11)	0.0011 (11)	0.0011 (10)
C15A	0.083 (2)	0.103 (2)	0.0737 (19)	−0.0332 (17)	−0.0007 (15)	0.0026 (17)
C16A	0.120 (3)	0.124 (3)	0.186 (5)	−0.062 (3)	0.051 (3)	−0.057 (3)
C17A	0.102 (3)	0.103 (3)	0.128 (3)	−0.022 (2)	−0.021 (2)	0.048 (2)
O1B	0.0451 (9)	0.0468 (9)	0.0835 (12)	0.0008 (7)	−0.0023 (8)	0.0072 (8)
O2B	0.0766 (12)	0.0687 (11)	0.0517 (11)	0.0012 (8)	−0.0092 (8)	−0.0092 (8)
N1B	0.109 (2)	0.0665 (17)	0.146 (3)	−0.0219 (15)	−0.0115 (18)	−0.0188 (16)
N2B	0.0563 (11)	0.0536 (11)	0.0437 (10)	−0.0097 (8)	0.0004 (9)	−0.0001 (8)
N3B	0.0703 (14)	0.0572 (13)	0.0681 (15)	−0.0167 (10)	−0.0219 (12)	0.0083 (11)
C1B	0.0402 (11)	0.0490 (12)	0.0626 (15)	−0.0002 (9)	−0.0025 (10)	0.0007 (10)
C2B	0.0428 (12)	0.0586 (14)	0.0512 (13)	−0.0002 (10)	−0.0053 (10)	0.0092 (10)
C3B	0.0570 (15)	0.0717 (16)	0.0721 (17)	0.0086 (12)	0.0044 (13)	0.0073 (13)
C4B	0.0570 (17)	0.103 (2)	0.079 (2)	0.0101 (15)	0.0143 (14)	0.0103 (17)
C5B	0.0547 (16)	0.110 (2)	0.0702 (18)	−0.0109 (16)	0.0091 (14)	0.0177 (16)
C6B	0.0627 (16)	0.0757 (17)	0.0560 (15)	−0.0176 (13)	−0.0053 (12)	0.0149 (12)
C7B	0.0498 (13)	0.0591 (14)	0.0476 (13)	−0.0053 (11)	−0.0102 (10)	0.0085 (10)
C8B	0.0592 (15)	0.0477 (13)	0.0709 (16)	−0.0048 (11)	−0.0127 (12)	0.0031 (11)
C9B	0.0483 (14)	0.0514 (14)	0.0853 (19)	0.0042 (11)	−0.0031 (13)	−0.0038 (12)
C10B	0.0497 (13)	0.0592 (14)	0.0517 (13)	−0.0053 (10)	−0.0033 (10)	−0.0056 (10)
C11B	0.0581 (15)	0.0580 (15)	0.0473 (14)	−0.0105 (12)	−0.0012 (12)	0.0026 (10)
C12B	0.0589 (14)	0.0733 (16)	0.0498 (14)	−0.0075 (12)	0.0068 (11)	0.0032 (11)
C13B	0.0517 (13)	0.0593 (14)	0.0640 (16)	−0.0062 (11)	0.0015 (11)	0.0127 (11)
C14B	0.0501 (12)	0.0438 (12)	0.0517 (14)	0.0066 (10)	−0.0043 (10)	−0.0042 (10)
C15B	0.075 (8)	0.071 (4)	0.063 (7)	−0.024 (5)	−0.001 (5)	0.005 (6)
C16B	0.129 (7)	0.128 (6)	0.092 (5)	−0.075 (6)	−0.017 (5)	0.023 (4)
C15C	0.069 (9)	0.070 (6)	0.058 (9)	−0.028 (6)	−0.003 (6)	0.011 (7)
C16C	0.142 (9)	0.063 (5)	0.114 (7)	−0.022 (5)	0.008 (6)	−0.008 (4)
C17B	0.0683 (17)	0.0597 (17)	0.099 (2)	−0.0108 (13)	−0.0089 (15)	−0.0035 (15)

O1A—C2A	1.374 (3)	N2B—C14B	1.369 (3)
O1A—C1A	1.437 (3)	N2B—C11B	1.455 (3)
O2A—C14A	1.232 (3)	N2B—C12B	1.465 (3)
N1A—C17A	1.134 (4)	N3B—C14B	1.330 (3)
N2A—C14A	1.373 (3)	N3B—C15B	1.466 (19)
N2A—C12A	1.468 (3)	N3B—C15C	1.47 (2)
N2A—C11A	1.470 (3)	N3B—H2N3	0.83 (2)
N3A—C14A	1.331 (3)	C1B—C9B	1.500 (3)
N3A—C15A	1.452 (4)	C1B—C10B	1.513 (3)
N3A—H1N3	0.81 (3)	C1B—C13B	1.519 (3)
C1A—C9A	1.469 (4)	C2B—C3B	1.371 (3)
C1A—C10A	1.516 (3)	C2B—C7B	1.388 (3)
C1A—C13A	1.526 (4)	C3B—C4B	1.381 (4)
C2A—C3A	1.358 (4)	C3B—H3B	0.9300
C2A—C7A	1.409 (4)	C4B—C5B	1.365 (4)
C3A—C4A	1.354 (6)	C4B—H4B	0.9300
C3A—H3A	0.9300	C5B—C6B	1.378 (4)
C4A—C5A	1.318 (8)	C5B—H5B	0.9300
C4A—H4A	1.03 (4)	C6B—C7B	1.391 (3)
C5A—C6A	1.437 (8)	C6B—H6B	0.9300
C5A—H5A	0.9300	C7B—C8B	1.464 (3)
C6A—C7A	1.377 (4)	C8B—C9B	1.326 (3)
C6A—H6A	0.9300	C8B—C17B	1.440 (4)
C7A—C8A	1.459 (4)	C9B—H9B	0.92 (3)
C8A—C9A	1.307 (4)	C10B—C11B	1.515 (3)
C8A—C17A	1.449 (5)	C10B—H10C	0.9700
C9A—H9A	0.94 (3)	C10B—H10D	0.9700
C10A—C11A	1.486 (4)	C11B—H11C	0.95 (3)
C10A—H10A	0.9700	C11B—H11D	1.01 (2)
C10A—H10B	0.9700	C12B—C13B	1.511 (3)
C11A—H11A	1.06 (3)	C12B—H12C	0.9700
C11A—H11B	1.00 (3)	C12B—H12D	0.9700
C12A—C13A	1.490 (4)	C13B—H13C	0.9700
C12A—H12A	0.9700	C13B—H13D	0.9700
C12A—H12B	0.9700	C15B—C16B	1.522 (14)
C13A—H13A	0.9700	C15B—H15C	0.9700
C13A—H13B	0.9700	C15B—H15D	0.9700
C15A—C16A	1.446 (5)	C16B—H16D	0.9600
C15A—H15A	0.9700	C16B—H16E	0.9600
C15A—H15B	0.9700	C16B—H16F	0.9600
C16A—H16A	0.9600	C15C—C16C	1.46 (2)
C16A—H16B	0.9600	C15C—H15E	0.9700
C16A—H16C	0.9600	C15C—H15F	0.9700
O1B—C2B	1.371 (3)	C16C—H16G	0.9600
O1B—C1B	1.454 (2)	C16C—H16H	0.9600
O2B—C14B	1.236 (3)	C16C—H16I	0.9600
N1B—C17B	1.140 (3)
C2A—O1A—C1A	119.4 (2)	C14B—N3B—C15B	113.3 (5)
C14A—N2A—C12A	116.2 (2)	C14B—N3B—C15C	130.6 (6)
C14A—N2A—C11A	121.5 (2)	C14B—N3B—H2N3	120.6 (16)
C12A—N2A—C11A	113.0 (2)	C15B—N3B—H2N3	121.0 (17)
C14A—N3A—C15A	121.8 (2)	C15C—N3B—H2N3	108.1 (18)
C14A—N3A—H1N3	120 (2)	O1B—C1B—C9B	109.72 (17)
C15A—N3A—H1N3	118.2 (19)	O1B—C1B—C10B	104.95 (17)
O1A—C1A—C9A	111.1 (2)	C9B—C1B—C10B	112.0 (2)
O1A—C1A—C10A	103.6 (2)	O1B—C1B—C13B	109.74 (18)
C9A—C1A—C10A	113.6 (2)	C9B—C1B—C13B	111.29 (19)
O1A—C1A—C13A	109.0 (2)	C10B—C1B—C13B	108.90 (17)
C9A—C1A—C13A	110.8 (2)	C3B—C2B—O1B	117.6 (2)
C10A—C1A—C13A	108.4 (2)	C3B—C2B—C7B	121.1 (2)
C3A—C2A—O1A	118.5 (3)	O1B—C2B—C7B	121.1 (2)
C3A—C2A—C7A	121.8 (3)	C2B—C3B—C4B	119.1 (3)
O1A—C2A—C7A	119.6 (3)	C2B—C3B—H3B	120.5
C4A—C3A—C2A	118.9 (5)	C4B—C3B—H3B	120.5
C4A—C3A—H3A	120.6	C5B—C4B—C3B	121.1 (3)
C2A—C3A—H3A	120.6	C5B—C4B—H4B	119.5
C5A—C4A—C3A	122.5 (5)	C3B—C4B—H4B	119.5
C5A—C4A—H4A	116 (2)	C4B—C5B—C6B	119.7 (3)
C3A—C4A—H4A	122 (3)	C4B—C5B—H5B	120.2
C4A—C5A—C6A	120.6 (4)	C6B—C5B—H5B	120.2
C4A—C5A—H5A	119.7	C5B—C6B—C7B	120.5 (3)
C6A—C5A—H5A	119.7	C5B—C6B—H6B	119.8
C7A—C6A—C5A	117.9 (4)	C7B—C6B—H6B	119.8
C7A—C6A—H6A	121.0	C2B—C7B—C6B	118.5 (2)
C5A—C6A—H6A	121.0	C2B—C7B—C8B	116.42 (19)
C6A—C7A—C2A	118.3 (4)	C6B—C7B—C8B	125.0 (2)
C6A—C7A—C8A	124.9 (4)	C9B—C8B—C17B	120.9 (2)
C2A—C7A—C8A	116.7 (2)	C9B—C8B—C7B	120.6 (2)
C9A—C8A—C17A	121.3 (4)	C17B—C8B—C7B	118.5 (2)
C9A—C8A—C7A	121.0 (3)	C8B—C9B—C1B	120.6 (2)
C17A—C8A—C7A	117.7 (3)	C8B—C9B—H9B	122.4 (16)
C8A—C9A—C1A	121.9 (3)	C1B—C9B—H9B	117.0 (16)
C8A—C9A—H9A	118 (2)	C1B—C10B—C11B	112.3 (2)
C1A—C9A—H9A	120 (2)	C1B—C10B—H10C	109.1
C11A—C10A—C1A	113.4 (2)	C11B—C10B—H10C	109.1
C11A—C10A—H10A	108.9	C1B—C10B—H10D	109.1
C1A—C10A—H10A	108.9	C11B—C10B—H10D	109.1
C11A—C10A—H10B	108.9	H10C—C10B—H10D	107.9
C1A—C10A—H10B	108.9	N2B—C11B—C10B	110.37 (19)
H10A—C10A—H10B	107.7	N2B—C11B—H11C	110.2 (15)
N2A—C11A—C10A	110.4 (2)	C10B—C11B—H11C	107.7 (15)
N2A—C11A—H11A	112.2 (16)	N2B—C11B—H11D	107.3 (13)
C10A—C11A—H11A	100.4 (16)	C10B—C11B—H11D	113.7 (13)
N2A—C11A—H11B	106.1 (15)	H11C—C11B—H11D	107 (2)
C10A—C11A—H11B	115.1 (15)	N2B—C12B—C13B	110.99 (19)
H11A—C11A—H11B	113 (2)	N2B—C12B—H12C	109.4
N2A—C12A—C13A	111.2 (2)	C13B—C12B—H12C	109.4
N2A—C12A—H12A	109.4	N2B—C12B—H12D	109.4
C13A—C12A—H12A	109.4	C13B—C12B—H12D	109.4
N2A—C12A—H12B	109.4	H12C—C12B—H12D	108.0
C13A—C12A—H12B	109.4	C12B—C13B—C1B	112.18 (19)
H12A—C12A—H12B	108.0	C12B—C13B—H13C	109.2
C12A—C13A—C1A	113.8 (2)	C1B—C13B—H13C	109.2
C12A—C13A—H13A	108.8	C12B—C13B—H13D	109.2
C1A—C13A—H13A	108.8	C1B—C13B—H13D	109.2
C12A—C13A—H13B	108.8	H13C—C13B—H13D	107.9
C1A—C13A—H13B	108.8	O2B—C14B—N3B	121.2 (2)
H13A—C13A—H13B	107.7	O2B—C14B—N2B	120.5 (2)
O2A—C14A—N3A	121.0 (2)	N3B—C14B—N2B	118.1 (2)
O2A—C14A—N2A	121.2 (2)	N3B—C15B—C16B	104.8 (8)
N3A—C14A—N2A	117.7 (2)	N3B—C15B—H15C	110.8
C16A—C15A—N3A	114.1 (3)	C16B—C15B—H15C	110.8
C16A—C15A—H15A	108.7	N3B—C15B—H15D	110.8
N3A—C15A—H15A	108.7	C16B—C15B—H15D	110.8
C16A—C15A—H15B	108.7	H15C—C15B—H15D	108.9
N3A—C15A—H15B	108.7	C16C—C15C—N3B	109.1 (14)
H15A—C15A—H15B	107.6	C16C—C15C—H15E	109.9
C15A—C16A—H16A	109.5	N3B—C15C—H15E	109.9
C15A—C16A—H16B	109.5	C16C—C15C—H15F	109.9
H16A—C16A—H16B	109.5	N3B—C15C—H15F	109.9
C15A—C16A—H16C	109.5	H15E—C15C—H15F	108.3
H16A—C16A—H16C	109.5	C15C—C16C—H16G	109.5
H16B—C16A—H16C	109.5	C15C—C16C—H16H	109.5
N1A—C17A—C8A	177.0 (5)	H16G—C16C—H16H	109.5
C2B—O1B—C1B	117.26 (16)	C15C—C16C—H16I	109.5
C14B—N2B—C11B	122.66 (18)	H16G—C16C—H16I	109.5
C14B—N2B—C12B	117.30 (18)	H16H—C16C—H16I	109.5
C11B—N2B—C12B	114.26 (18)	N1B—C17B—C8B	178.9 (4)
C2A—O1A—C1A—C9A	−38.2 (3)	C1B—O1B—C2B—C3B	153.4 (2)
C2A—O1A—C1A—C10A	−160.6 (2)	C1B—O1B—C2B—C7B	−31.4 (3)
C2A—O1A—C1A—C13A	84.2 (3)	O1B—C2B—C3B—C4B	175.5 (2)
C1A—O1A—C2A—C3A	−157.3 (3)	C7B—C2B—C3B—C4B	0.3 (4)
C1A—O1A—C2A—C7A	27.4 (4)	C2B—C3B—C4B—C5B	0.7 (4)
O1A—C2A—C3A—C4A	−174.1 (3)	C3B—C4B—C5B—C6B	−0.8 (4)
C7A—C2A—C3A—C4A	1.1 (5)	C4B—C5B—C6B—C7B	0.1 (4)
C2A—C3A—C4A—C5A	−0.5 (6)	C3B—C2B—C7B—C6B	−1.0 (3)
C3A—C4A—C5A—C6A	−0.8 (7)	O1B—C2B—C7B—C6B	−176.04 (19)
C4A—C5A—C6A—C7A	1.4 (6)	C3B—C2B—C7B—C8B	176.1 (2)
C5A—C6A—C7A—C2A	−0.8 (4)	O1B—C2B—C7B—C8B	1.1 (3)
C5A—C6A—C7A—C8A	176.1 (3)	C5B—C6B—C7B—C2B	0.8 (3)
C3A—C2A—C7A—C6A	−0.4 (4)	C5B—C6B—C7B—C8B	−176.0 (2)
O1A—C2A—C7A—C6A	174.7 (2)	C2B—C7B—C8B—C9B	13.7 (3)
C3A—C2A—C7A—C8A	−177.5 (3)	C6B—C7B—C8B—C9B	−169.4 (2)
O1A—C2A—C7A—C8A	−2.4 (4)	C2B—C7B—C8B—C17B	−164.4 (2)
C6A—C7A—C8A—C9A	173.9 (3)	C6B—C7B—C8B—C17B	12.5 (4)
C2A—C7A—C8A—C9A	−9.2 (4)	C17B—C8B—C9B—C1B	−179.8 (2)
C6A—C7A—C8A—C17A	−7.6 (4)	C7B—C8B—C9B—C1B	2.1 (4)
C2A—C7A—C8A—C17A	169.3 (2)	O1B—C1B—C9B—C8B	−29.7 (3)
C17A—C8A—C9A—C1A	177.4 (3)	C10B—C1B—C9B—C8B	−145.8 (2)
C7A—C8A—C9A—C1A	−4.2 (4)	C13B—C1B—C9B—C8B	92.0 (3)
O1A—C1A—C9A—C8A	26.8 (4)	O1B—C1B—C10B—C11B	62.5 (2)
C10A—C1A—C9A—C8A	143.1 (3)	C9B—C1B—C10B—C11B	−178.47 (19)
C13A—C1A—C9A—C8A	−94.6 (3)	C13B—C1B—C10B—C11B	−54.9 (2)
O1A—C1A—C10A—C11A	−62.8 (3)	C14B—N2B—C11B—C10B	152.5 (2)
C9A—C1A—C10A—C11A	176.5 (2)	C12B—N2B—C11B—C10B	−55.1 (3)
C13A—C1A—C10A—C11A	52.8 (3)	C1B—C10B—C11B—N2B	55.4 (3)
C14A—N2A—C11A—C10A	−158.1 (2)	C14B—N2B—C12B—C13B	−151.31 (19)
C12A—N2A—C11A—C10A	56.5 (3)	C11B—N2B—C12B—C13B	54.7 (3)
C1A—C10A—C11A—N2A	−56.3 (3)	N2B—C12B—C13B—C1B	−53.9 (3)
C14A—N2A—C12A—C13A	157.7 (2)	O1B—C1B—C13B—C12B	−60.2 (2)
C11A—N2A—C12A—C13A	−54.9 (3)	C9B—C1B—C13B—C12B	178.10 (19)
N2A—C12A—C13A—C1A	52.8 (3)	C10B—C1B—C13B—C12B	54.1 (2)
O1A—C1A—C13A—C12A	61.0 (3)	C15B—N3B—C14B—O2B	−13.1 (8)
C9A—C1A—C13A—C12A	−176.4 (3)	C15C—N3B—C14B—O2B	1.9 (11)
C10A—C1A—C13A—C12A	−51.0 (3)	C15B—N3B—C14B—N2B	171.4 (8)
C15A—N3A—C14A—O2A	0.5 (4)	C15C—N3B—C14B—N2B	−173.7 (10)
C15A—N3A—C14A—N2A	177.4 (3)	C11B—N2B—C14B—O2B	173.9 (2)
C12A—N2A—C14A—O2A	−9.0 (4)	C12B—N2B—C14B—O2B	22.2 (3)
C11A—N2A—C14A—O2A	−153.3 (3)	C11B—N2B—C14B—N3B	−10.5 (3)
C12A—N2A—C14A—N3A	174.1 (2)	C12B—N2B—C14B—N3B	−162.2 (2)
C11A—N2A—C14A—N3A	29.8 (3)	C14B—N3B—C15B—C16B	162.7 (8)
C14A—N3A—C15A—C16A	−128.1 (4)	C15C—N3B—C15B—C16B	15 (3)
C2B—O1B—C1B—C9B	43.8 (3)	C14B—N3B—C15C—C16C	−106.6 (11)
C2B—O1B—C1B—C10B	164.34 (18)	C15B—N3B—C15C—C16C	−66 (4)
C2B—O1B—C1B—C13B	−78.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H1N3···O2Ai	0.81 (3)	2.12 (3)	2.915 (3)	170 (3)
N3B—H2N3···O2Bii	0.83 (2)	2.19 (3)	2.983 (3)	160 (2)
C11A—H11B···O2Ai	1.00 (3)	2.27 (3)	3.246 (3)	165 (2)
C11B—H11C···O2Bii	0.95 (3)	2.50 (3)	3.344 (3)	147 (2)
C9B—H9B···O2Biii	0.92 (3)	2.58 (3)	3.473 (3)	163 (2)
C13A—H13B···Cg1iv	0.97	2.91	3.843 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4B–C9B benzene ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3A—H1N3⋯O2A i	0.81 (3)	2.12 (3)	2.915 (3)	170 (3)
N3B—H2N3⋯O2B ii	0.83 (2)	2.19 (3)	2.983 (3)	160 (2)
C11A—H11B⋯O2A i	1.00 (3)	2.27 (3)	3.246 (3)	165 (2)
C11B—H11C⋯O2B ii	0.95 (3)	2.50 (3)	3.344 (3)	147 (2)
C9B—H9B⋯O2B iii	0.92 (3)	2.58 (3)	3.473 (3)	163 (2)
C13A—H13B⋯Cg1iv	0.97	2.91	3.843 (3)	163

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .