(4-But-oxy-phen-yl)(1H-pyrrol-2-yl)methanone.

The asymmetric unit of the title compound, C(15)H(17)NO(2), contains two independent mol-ecules in which the dihedral angles between the pyrrole and benzene rings are 42.43 (9) and 45.70 (9)°. In both mol-ecules, the but-oxy chains are disordered over two sets of sites, with occupancy ratios of 0.701 (7):0.299 (7) and 0.869 (4):0.131 (4). Each mol-ecule forms a dimer with an inversion-related mol-ecule, through a pair of N-H⋯O hydrogen bonds. Weak C-H⋯O inter-actions link these dimers in the crystal structure.

Related literature

For background and applications of pyrrole derivatives, see: Fischer & Orth (1934 ▶); Mohamed et al. (2009 ▶). For related structures, see: English et al. (1980 ▶).

Experimental

Crystal data

C15H17NO2

M = 243.30

Triclinic,

a = 9.4779 (4) Å

b = 11.4478 (5) Å

c = 13.1117 (7) Å

α = 95.155 (4)°

β = 104.118 (4)°

γ = 94.626 (3)°

V = 1366.31 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.935, T max = 1.000

13503 measured reflections

5344 independent reflections

3273 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.160

S = 1.03

5344 reflections

385 parameters

38 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017370/bh2427sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017370/bh2427Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017370/bh2427Isup3.cml

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

C15H17NO2	Z = 4
Mr = 243.30	F(000) = 520
Triclinic, P1	Dx = 1.183 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4779 (4) Å	Cell parameters from 4854 reflections
b = 11.4478 (5) Å	θ = 3.5–29.0°
c = 13.1117 (7) Å	µ = 0.08 mm−1
α = 95.155 (4)°	T = 293 K
β = 104.118 (4)°	Block, brown
γ = 94.626 (3)°	0.3 × 0.2 × 0.2 mm
V = 1366.31 (11) Å3

Oxford Diffraction Xcalibur Sapphire3 diffractometer	5344 independent reflections
Radiation source: fine-focus sealed tube	3273 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −14→14
Tmin = 0.935, Tmax = 1.000	l = −16→16
13503 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.160	w = 1/[σ2(Fo2) + (0.0667P)2 + 0.1402P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.002
5344 reflections	Δρmax = 0.32 e Å−3
385 parameters	Δρmin = −0.18 e Å−3
38 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.013 (2)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.3964 (2)	0.38234 (18)	0.58381 (17)	0.0676 (5)
H1A	0.415 (3)	0.456 (2)	0.5625 (19)	0.080 (8)*
C2A	0.4091 (2)	0.27769 (18)	0.52819 (17)	0.0570 (6)
C3A	0.3733 (3)	0.1891 (2)	0.58493 (19)	0.0701 (6)
H3A	0.3731	0.1086	0.5669	0.084*
C4A	0.3373 (3)	0.2415 (2)	0.6740 (2)	0.0853 (8)
H4A	0.3086	0.2028	0.7262	0.102*
C5A	0.3522 (3)	0.3598 (3)	0.6703 (2)	0.0838 (8)
H5A	0.3344	0.4163	0.7200	0.101*
C6A	0.4623 (2)	0.27838 (17)	0.43447 (16)	0.0533 (5)
O7A	0.51771 (17)	0.37123 (12)	0.41197 (12)	0.0678 (4)
C8A	0.4488 (2)	0.16796 (16)	0.36334 (15)	0.0505 (5)
C9A	0.3340 (2)	0.08001 (17)	0.34810 (16)	0.0549 (5)
H9A	0.2654	0.0873	0.3877	0.066*
C10A	0.3189 (2)	−0.01866 (18)	0.27531 (17)	0.0592 (6)
H10A	0.2407	−0.0765	0.2658	0.071*
C11A	0.4209 (3)	−0.03003 (17)	0.21720 (17)	0.0589 (6)
C12A	0.5375 (3)	0.05661 (18)	0.23217 (18)	0.0626 (6)
H12A	0.6070	0.0485	0.1935	0.075*
C13A	0.5504 (2)	0.15421 (17)	0.30394 (17)	0.0579 (6)
H13A	0.6285	0.2121	0.3129	0.069*
O14A	0.4161 (2)	−0.12257 (13)	0.14272 (13)	0.0798 (5)
C15A	0.3187 (7)	−0.2278 (4)	0.1406 (5)	0.0747 (17)	0.701 (7)
H15A	0.2176	−0.2116	0.1176	0.090*	0.701 (7)
H15B	0.3347	−0.2530	0.2108	0.090*	0.701 (7)
C16A	0.3504 (6)	−0.3227 (3)	0.0649 (3)	0.0749 (14)	0.701 (7)
H161	0.4519	−0.3373	0.0894	0.090*	0.701 (7)
H162	0.2902	−0.3948	0.0664	0.090*	0.701 (7)
C17A	0.3236 (6)	−0.2945 (4)	−0.0474 (3)	0.0872 (15)	0.701 (7)
H171	0.3879	−0.2250	−0.0499	0.105*	0.701 (7)
H172	0.2236	−0.2761	−0.0711	0.105*	0.701 (7)
C18A	0.3490 (11)	−0.3948 (5)	−0.1226 (5)	0.0885 (19)	0.701 (7)
H181	0.4461	−0.4167	−0.0973	0.133*	0.701 (7)
H182	0.3381	−0.3698	−0.1918	0.133*	0.701 (7)
H183	0.2789	−0.4614	−0.1261	0.133*	0.701 (7)
C15C	0.2747 (12)	−0.1933 (10)	0.1086 (9)	0.072 (4)	0.299 (7)
H15C	0.1977	−0.1416	0.0956	0.086*	0.299 (7)
H15D	0.2610	−0.2397	0.1645	0.086*	0.299 (7)
C16C	0.2635 (10)	−0.2746 (8)	0.0093 (9)	0.081 (3)	0.299 (7)
H163	0.1744	−0.3280	−0.0049	0.097*	0.299 (7)
H164	0.2563	−0.2280	−0.0497	0.097*	0.299 (7)
C17C	0.3914 (12)	−0.3461 (10)	0.0157 (9)	0.095 (4)	0.299 (7)
H173	0.3998	−0.3924	0.0749	0.114*	0.299 (7)
H174	0.4807	−0.2932	0.0284	0.114*	0.299 (7)
C18C	0.375 (3)	−0.4285 (15)	−0.0856 (10)	0.093 (5)	0.299 (7)
H184	0.2962	−0.4895	−0.0920	0.139*	0.299 (7)
H185	0.4639	−0.4633	−0.0832	0.139*	0.299 (7)
H186	0.3528	−0.3845	−0.1455	0.139*	0.299 (7)
N1B	0.0500 (2)	0.87463 (18)	0.59698 (16)	0.0639 (5)
H1B	0.042 (3)	0.947 (2)	0.5801 (18)	0.075 (8)*
C2B	0.0550 (2)	0.78032 (17)	0.52617 (17)	0.0567 (5)
C3B	0.0572 (3)	0.6824 (2)	0.5801 (2)	0.0712 (7)
H3B	0.0602	0.6053	0.5523	0.085*
C4B	0.0540 (3)	0.7193 (2)	0.6838 (2)	0.0781 (7)
H4B	0.0546	0.6717	0.7377	0.094*
C5B	0.0497 (3)	0.8383 (2)	0.6909 (2)	0.0716 (7)
H5B	0.0469	0.8864	0.7513	0.086*
C6B	0.0488 (2)	0.79522 (18)	0.41681 (18)	0.0586 (6)
O7B	0.01924 (19)	0.88961 (13)	0.38164 (12)	0.0746 (5)
C8B	0.0762 (2)	0.69620 (17)	0.34547 (17)	0.0553 (5)
C9B	0.1814 (2)	0.62104 (18)	0.37939 (17)	0.0618 (6)
H9B	0.2352	0.6310	0.4497	0.074*
C10B	0.2078 (2)	0.53160 (18)	0.31047 (18)	0.0627 (6)
H10B	0.2805	0.4833	0.3343	0.075*
C11B	0.1270 (2)	0.51385 (17)	0.20688 (17)	0.0547 (5)
C12B	0.0225 (2)	0.58900 (18)	0.17103 (17)	0.0587 (6)
H12B	−0.0316	0.5784	0.1008	0.070*
C13B	−0.0008 (2)	0.67900 (18)	0.23941 (17)	0.0596 (6)
H13B	−0.0698	0.7298	0.2143	0.072*
O14B	0.14249 (17)	0.42661 (12)	0.13369 (12)	0.0673 (4)
C15B	0.2520 (3)	0.3485 (2)	0.1675 (2)	0.0840 (8)
H15E	0.2263	0.3027	0.2204	0.101*	0.869 (4)
H15F	0.3461	0.3939	0.1988	0.101*	0.869 (4)
H15G	0.2512	0.3191	0.2345	0.101*	0.131 (4)
H15H	0.3497	0.3793	0.1658	0.101*	0.131 (4)
C16B	0.2609 (4)	0.2670 (3)	0.0721 (3)	0.0886 (11)	0.869 (4)
H165	0.2643	0.3134	0.0142	0.106*	0.869 (4)
H166	0.3511	0.2302	0.0894	0.106*	0.869 (4)
C17B	0.1392 (5)	0.1761 (3)	0.0378 (3)	0.1069 (13)	0.869 (4)
H175	0.0510	0.2122	0.0093	0.128*	0.869 (4)
H176	0.1257	0.1384	0.0986	0.128*	0.869 (4)
C18B	0.1608 (6)	0.0812 (5)	−0.0471 (3)	0.127 (2)	0.869 (4)
H18A	0.1743	0.1178	−0.1075	0.191*	0.869 (4)
H18B	0.0760	0.0242	−0.0681	0.191*	0.869 (4)
H18C	0.2454	0.0425	−0.0183	0.191*	0.869 (4)
C16D	0.188 (2)	0.2305 (13)	0.1055 (19)	0.0886 (11)	0.131 (4)
H16A	0.1455	0.1854	0.1521	0.106*	0.131 (4)
H16B	0.1069	0.2457	0.0485	0.106*	0.131 (4)
C17D	0.278 (3)	0.151 (2)	0.0574 (17)	0.1069 (13)	0.131 (4)
H17A	0.2925	0.0863	0.1002	0.128*	0.131 (4)
H17B	0.3732	0.1952	0.0680	0.128*	0.131 (4)
C18D	0.234 (5)	0.097 (4)	−0.057 (2)	0.127 (2)	0.131 (4)
H18D	0.1298	0.0778	−0.0793	0.191*	0.131 (4)
H18E	0.2808	0.0261	−0.0639	0.191*	0.131 (4)
H18F	0.2637	0.1518	−0.1011	0.191*	0.131 (4)

	U11	U22	U33	U12	U13	U23
N1A	0.0743 (14)	0.0553 (12)	0.0701 (13)	0.0051 (10)	0.0195 (10)	−0.0120 (10)
C2A	0.0581 (13)	0.0514 (12)	0.0563 (13)	0.0084 (10)	0.0085 (10)	−0.0072 (10)
C3A	0.0808 (17)	0.0638 (14)	0.0656 (15)	0.0095 (12)	0.0203 (13)	0.0002 (12)
C4A	0.102 (2)	0.0872 (19)	0.0708 (17)	0.0053 (16)	0.0345 (15)	0.0026 (14)
C5A	0.091 (2)	0.088 (2)	0.0722 (17)	0.0070 (15)	0.0302 (15)	−0.0166 (14)
C6A	0.0511 (13)	0.0462 (12)	0.0567 (13)	0.0074 (10)	0.0042 (10)	−0.0018 (10)
O7A	0.0819 (11)	0.0456 (8)	0.0726 (10)	0.0007 (8)	0.0189 (9)	−0.0024 (7)
C8A	0.0514 (12)	0.0452 (11)	0.0526 (12)	0.0069 (9)	0.0101 (10)	−0.0001 (9)
C9A	0.0508 (13)	0.0577 (12)	0.0553 (13)	0.0039 (10)	0.0163 (10)	−0.0052 (10)
C10A	0.0570 (13)	0.0547 (12)	0.0625 (13)	−0.0083 (10)	0.0182 (11)	−0.0076 (10)
C11A	0.0721 (15)	0.0468 (12)	0.0590 (13)	−0.0006 (10)	0.0257 (11)	−0.0079 (10)
C12A	0.0665 (15)	0.0541 (13)	0.0724 (15)	−0.0009 (11)	0.0339 (12)	−0.0047 (11)
C13A	0.0559 (13)	0.0463 (11)	0.0692 (14)	−0.0043 (9)	0.0176 (11)	−0.0014 (10)
O14A	0.0978 (13)	0.0611 (10)	0.0833 (12)	−0.0177 (9)	0.0482 (10)	−0.0234 (8)
C15A	0.104 (4)	0.046 (3)	0.077 (3)	−0.018 (2)	0.041 (3)	−0.009 (2)
C16A	0.097 (4)	0.056 (2)	0.075 (3)	−0.011 (2)	0.038 (3)	−0.003 (2)
C17A	0.102 (3)	0.088 (3)	0.072 (3)	0.014 (3)	0.029 (3)	−0.011 (2)
C18A	0.117 (5)	0.079 (4)	0.072 (4)	0.006 (3)	0.038 (4)	−0.013 (3)
C15C	0.106 (9)	0.036 (6)	0.073 (8)	−0.012 (5)	0.035 (6)	−0.015 (5)
C16C	0.085 (7)	0.076 (6)	0.079 (8)	0.002 (5)	0.023 (6)	−0.006 (5)
C17C	0.126 (10)	0.104 (8)	0.068 (8)	0.015 (7)	0.049 (7)	0.015 (6)
C18C	0.118 (10)	0.093 (9)	0.076 (9)	0.020 (8)	0.042 (8)	−0.006 (7)
N1B	0.0719 (13)	0.0550 (12)	0.0665 (13)	0.0095 (10)	0.0214 (10)	0.0025 (10)
C2B	0.0596 (14)	0.0480 (12)	0.0604 (14)	0.0006 (10)	0.0154 (11)	−0.0021 (10)
C3B	0.0794 (17)	0.0531 (13)	0.0778 (17)	−0.0040 (11)	0.0190 (13)	0.0020 (12)
C4B	0.0880 (19)	0.0750 (17)	0.0723 (17)	−0.0023 (13)	0.0222 (14)	0.0169 (13)
C5B	0.0720 (17)	0.0831 (18)	0.0608 (15)	0.0056 (13)	0.0219 (12)	0.0027 (13)
C6B	0.0597 (14)	0.0490 (12)	0.0670 (15)	0.0033 (10)	0.0187 (11)	0.0004 (11)
O7B	0.1014 (13)	0.0535 (9)	0.0751 (11)	0.0211 (8)	0.0294 (9)	0.0081 (8)
C8B	0.0596 (13)	0.0458 (11)	0.0596 (13)	0.0052 (10)	0.0153 (11)	0.0017 (10)
C9B	0.0634 (14)	0.0563 (13)	0.0582 (13)	0.0077 (11)	0.0037 (11)	−0.0025 (10)
C10B	0.0622 (14)	0.0540 (13)	0.0683 (15)	0.0132 (11)	0.0089 (12)	0.0030 (11)
C11B	0.0573 (13)	0.0459 (11)	0.0601 (13)	0.0017 (10)	0.0171 (11)	−0.0011 (10)
C12B	0.0609 (14)	0.0594 (13)	0.0549 (13)	0.0080 (11)	0.0127 (11)	0.0053 (10)
C13B	0.0619 (14)	0.0583 (13)	0.0608 (14)	0.0153 (10)	0.0155 (11)	0.0110 (11)
O14B	0.0763 (11)	0.0571 (9)	0.0655 (10)	0.0110 (8)	0.0159 (8)	−0.0061 (7)
C15B	0.0922 (19)	0.0690 (16)	0.0907 (19)	0.0299 (14)	0.0213 (15)	−0.0065 (14)
C16B	0.103 (3)	0.071 (2)	0.101 (3)	0.0203 (19)	0.042 (2)	0.0037 (17)
C17B	0.142 (4)	0.082 (2)	0.089 (3)	0.009 (2)	0.023 (2)	−0.0127 (19)
C18B	0.209 (6)	0.080 (3)	0.090 (2)	0.008 (3)	0.045 (3)	−0.016 (2)
C16D	0.103 (3)	0.071 (2)	0.101 (3)	0.0203 (19)	0.042 (2)	0.0037 (17)
C17D	0.142 (4)	0.082 (2)	0.089 (3)	0.009 (2)	0.023 (2)	−0.0127 (19)
C18D	0.209 (6)	0.080 (3)	0.090 (2)	0.008 (3)	0.045 (3)	−0.016 (2)

N1A—C5A	1.340 (3)	N1B—C5B	1.335 (3)
N1A—C2A	1.375 (3)	N1B—C2B	1.371 (3)
N1A—H1A	0.92 (2)	N1B—H1B	0.88 (2)
C2A—C3A	1.379 (3)	C2B—C3B	1.377 (3)
C2A—C6A	1.438 (3)	C2B—C6B	1.447 (3)
C3A—C4A	1.394 (3)	C3B—C4B	1.395 (3)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.356 (4)	C4B—C5B	1.362 (3)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—O7A	1.239 (2)	C6B—O7B	1.239 (2)
C6A—C8A	1.479 (3)	C6B—C8B	1.484 (3)
C8A—C9A	1.385 (3)	C8B—C9B	1.387 (3)
C8A—C13A	1.388 (3)	C8B—C13B	1.392 (3)
C9A—C10A	1.386 (3)	C9B—C10B	1.383 (3)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.376 (3)	C10B—C11B	1.375 (3)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—O14A	1.365 (2)	C11B—O14B	1.364 (2)
C11A—C12A	1.388 (3)	C11B—C12B	1.387 (3)
C12A—C13A	1.372 (3)	C12B—C13B	1.372 (3)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—H13A	0.9300	C13B—H13B	0.9300
O14A—C15A	1.451 (5)	O14B—C15B	1.439 (3)
O14A—C15C	1.456 (9)	C15B—C16D	1.512 (10)
C15A—C16A	1.503 (6)	C15B—C16B	1.515 (3)
C15A—H15A	0.9700	C15B—H15E	0.9700
C15A—H15B	0.9700	C15B—H15F	0.9700
C16A—C17A	1.501 (5)	C15B—H15G	0.9700
C16A—H161	0.9700	C15B—H15H	0.9700
C16A—H162	0.9700	C16B—C17B	1.444 (5)
C17A—C18A	1.518 (6)	C16B—H165	0.9700
C17A—H171	0.9700	C16B—H166	0.9700
C17A—H172	0.9700	C17B—C18B	1.546 (5)
C18A—H181	0.9600	C17B—H175	0.9700
C18A—H182	0.9600	C17B—H176	0.9700
C18A—H183	0.9600	C18B—H18A	0.9600
C15C—C16C	1.507 (9)	C18B—H18B	0.9600
C15C—H15C	0.9700	C18B—H18C	0.9600
C15C—H15D	0.9700	C16D—C17D	1.496 (10)
C16C—C17C	1.506 (9)	C16D—H16A	0.9700
C16C—H163	0.9700	C16D—H16B	0.9700
C16C—H164	0.9700	C17D—C18D	1.519 (10)
C17C—C18C	1.525 (9)	C17D—H17A	0.9700
C17C—H173	0.9700	C17D—H17B	0.9700
C17C—H174	0.9700	C18D—H18D	0.9600
C18C—H184	0.9600	C18D—H18E	0.9600
C18C—H185	0.9600	C18D—H18F	0.9600
C18C—H186	0.9600
C5A—N1A—C2A	109.3 (2)	C17C—C18C—H186	109.5
C5A—N1A—H1A	126.9 (15)	H184—C18C—H186	109.5
C2A—N1A—H1A	123.8 (15)	H185—C18C—H186	109.5
N1A—C2A—C3A	106.6 (2)	C5B—N1B—C2B	109.9 (2)
N1A—C2A—C6A	120.1 (2)	C5B—N1B—H1B	126.4 (15)
C3A—C2A—C6A	133.22 (19)	C2B—N1B—H1B	123.6 (15)
C2A—C3A—C4A	107.9 (2)	N1B—C2B—C3B	106.4 (2)
C2A—C3A—H3A	126.1	N1B—C2B—C6B	120.85 (18)
C4A—C3A—H3A	126.1	C3B—C2B—C6B	132.7 (2)
C5A—C4A—C3A	107.1 (2)	C2B—C3B—C4B	108.0 (2)
C5A—C4A—H4A	126.5	C2B—C3B—H3B	126.0
C3A—C4A—H4A	126.5	C4B—C3B—H3B	126.0
N1A—C5A—C4A	109.2 (2)	C5B—C4B—C3B	106.9 (2)
N1A—C5A—H5A	125.4	C5B—C4B—H4B	126.5
C4A—C5A—H5A	125.4	C3B—C4B—H4B	126.5
O7A—C6A—C2A	120.48 (18)	N1B—C5B—C4B	108.8 (2)
O7A—C6A—C8A	119.59 (19)	N1B—C5B—H5B	125.6
C2A—C6A—C8A	119.92 (19)	C4B—C5B—H5B	125.6
C9A—C8A—C13A	117.99 (18)	O7B—C6B—C2B	120.60 (19)
C9A—C8A—C6A	122.99 (18)	O7B—C6B—C8B	119.5 (2)
C13A—C8A—C6A	118.90 (19)	C2B—C6B—C8B	119.88 (18)
C8A—C9A—C10A	121.60 (19)	C9B—C8B—C13B	117.58 (19)
C8A—C9A—H9A	119.2	C9B—C8B—C6B	122.3 (2)
C10A—C9A—H9A	119.2	C13B—C8B—C6B	120.08 (18)
C11A—C10A—C9A	119.27 (19)	C10B—C9B—C8B	121.1 (2)
C11A—C10A—H10A	120.4	C10B—C9B—H9B	119.4
C9A—C10A—H10A	120.4	C8B—C9B—H9B	119.4
O14A—C11A—C10A	124.27 (19)	C11B—C10B—C9B	120.23 (19)
O14A—C11A—C12A	115.79 (18)	C11B—C10B—H10B	119.9
C10A—C11A—C12A	119.94 (19)	C9B—C10B—H10B	119.9
C13A—C12A—C11A	120.14 (19)	O14B—C11B—C10B	124.59 (18)
C13A—C12A—H12A	119.9	O14B—C11B—C12B	115.90 (19)
C11A—C12A—H12A	119.9	C10B—C11B—C12B	119.50 (19)
C12A—C13A—C8A	121.06 (19)	C13B—C12B—C11B	119.8 (2)
C12A—C13A—H13A	119.5	C13B—C12B—H12B	120.1
C8A—C13A—H13A	119.5	C11B—C12B—H12B	120.1
C11A—O14A—C15A	118.1 (3)	C12B—C13B—C8B	121.65 (19)
C11A—O14A—C15C	113.8 (5)	C12B—C13B—H13B	119.2
O14A—C15A—C16A	108.0 (4)	C8B—C13B—H13B	119.2
O14A—C15A—H15A	110.1	C11B—O14B—C15B	117.42 (17)
C16A—C15A—H15A	110.1	O14B—C15B—C16D	104.5 (9)
O14A—C15A—H15B	110.1	O14B—C15B—C16B	108.6 (2)
C16A—C15A—H15B	110.1	O14B—C15B—H15E	110.0
H15A—C15A—H15B	108.4	C16B—C15B—H15E	110.0
C17A—C16A—C15A	114.5 (5)	O14B—C15B—H15F	110.0
C17A—C16A—H161	108.6	C16B—C15B—H15F	110.0
C15A—C16A—H161	108.6	H15E—C15B—H15F	108.4
C17A—C16A—H162	108.6	O14B—C15B—H15G	114.2
C15A—C16A—H162	108.6	C16B—C15B—H15G	121.5
H161—C16A—H162	107.6	O14B—C15B—H15H	113.8
C16A—C17A—C18A	113.1 (5)	C16D—C15B—H15H	118.5
C16A—C17A—H171	109.0	H15E—C15B—H15H	126.6
C18A—C17A—H171	109.0	H15G—C15B—H15H	111.7
C16A—C17A—H172	109.0	C17B—C16B—C15B	113.1 (3)
C18A—C17A—H172	109.0	C17B—C16B—H165	109.0
H171—C17A—H172	107.8	C15B—C16B—H165	109.0
O14A—C15C—C16C	111.5 (8)	C17B—C16B—H166	109.0
O14A—C15C—H15C	109.3	C15B—C16B—H166	109.0
C16C—C15C—H15C	109.3	H165—C16B—H166	107.8
O14A—C15C—H15D	109.3	C16B—C17B—C18B	113.0 (3)
C16C—C15C—H15D	109.3	C16B—C17B—H175	109.0
H15C—C15C—H15D	108.0	C18B—C17B—H175	109.0
C17C—C16C—C15C	113.5 (10)	C16B—C17B—H176	109.0
C17C—C16C—H163	108.9	C18B—C17B—H176	109.0
C15C—C16C—H163	108.9	H175—C17B—H176	107.8
C17C—C16C—H164	108.9	C17D—C16D—C15B	122.0 (15)
C15C—C16C—H164	108.9	C17D—C16D—H16A	106.8
H163—C16C—H164	107.7	C15B—C16D—H16A	106.8
C16C—C17C—C18C	111.8 (12)	C17D—C16D—H16B	106.8
C16C—C17C—H173	109.2	C15B—C16D—H16B	106.8
C18C—C17C—H173	109.2	H16A—C16D—H16B	106.7
C16C—C17C—H174	109.2	C16D—C17D—C18D	124 (3)
C18C—C17C—H174	109.3	C16D—C17D—H17A	106.4
H173—C17C—H174	107.9	C18D—C17D—H17A	106.4
C17C—C18C—H184	109.5	C16D—C17D—H17B	106.4
C17C—C18C—H185	109.5	C18D—C17D—H17B	106.4
H184—C18C—H185	109.5	H17A—C17D—H17B	106.5
C5A—N1A—C2A—C3A	−1.0 (3)	C15C—C16C—C17C—C18C	179.1 (11)
C5A—N1A—C2A—C6A	−176.9 (2)	C5B—N1B—C2B—C3B	0.2 (3)
N1A—C2A—C3A—C4A	0.7 (3)	C5B—N1B—C2B—C6B	176.8 (2)
C6A—C2A—C3A—C4A	175.8 (2)	N1B—C2B—C3B—C4B	−0.2 (3)
C2A—C3A—C4A—C5A	−0.2 (3)	C6B—C2B—C3B—C4B	−176.2 (2)
C2A—N1A—C5A—C4A	0.9 (3)	C2B—C3B—C4B—C5B	0.1 (3)
C3A—C4A—C5A—N1A	−0.4 (3)	C2B—N1B—C5B—C4B	−0.2 (3)
N1A—C2A—C6A—O7A	11.1 (3)	C3B—C4B—C5B—N1B	0.0 (3)
C3A—C2A—C6A—O7A	−163.5 (2)	N1B—C2B—C6B—O7B	−9.8 (3)
N1A—C2A—C6A—C8A	−168.00 (18)	C3B—C2B—C6B—O7B	165.7 (2)
C3A—C2A—C6A—C8A	17.5 (4)	N1B—C2B—C6B—C8B	171.02 (18)
O7A—C6A—C8A—C9A	−146.7 (2)	C3B—C2B—C6B—C8B	−13.4 (4)
C2A—C6A—C8A—C9A	32.4 (3)	O7B—C6B—C8B—C9B	142.7 (2)
O7A—C6A—C8A—C13A	29.2 (3)	C2B—C6B—C8B—C9B	−38.1 (3)
C2A—C6A—C8A—C13A	−151.68 (19)	O7B—C6B—C8B—C13B	−34.7 (3)
C13A—C8A—C9A—C10A	−0.6 (3)	C2B—C6B—C8B—C13B	144.5 (2)
C6A—C8A—C9A—C10A	175.36 (19)	C13B—C8B—C9B—C10B	−0.6 (3)
C8A—C9A—C10A—C11A	0.4 (3)	C6B—C8B—C9B—C10B	−178.0 (2)
C9A—C10A—C11A—O14A	−179.3 (2)	C8B—C9B—C10B—C11B	−1.6 (3)
C9A—C10A—C11A—C12A	0.2 (3)	C9B—C10B—C11B—O14B	−178.45 (19)
O14A—C11A—C12A—C13A	178.81 (19)	C9B—C10B—C11B—C12B	2.4 (3)
C10A—C11A—C12A—C13A	−0.7 (3)	O14B—C11B—C12B—C13B	179.75 (18)
C11A—C12A—C13A—C8A	0.5 (3)	C10B—C11B—C12B—C13B	−1.0 (3)
C9A—C8A—C13A—C12A	0.1 (3)	C11B—C12B—C13B—C8B	−1.2 (3)
C6A—C8A—C13A—C12A	−176.02 (19)	C9B—C8B—C13B—C12B	2.0 (3)
C10A—C11A—O14A—C15A	−14.7 (4)	C6B—C8B—C13B—C12B	179.5 (2)
C12A—C11A—O14A—C15A	165.8 (4)	C10B—C11B—O14B—C15B	−0.5 (3)
C10A—C11A—O14A—C15C	15.6 (6)	C12B—C11B—O14B—C15B	178.7 (2)
C12A—C11A—O14A—C15C	−163.9 (6)	C11B—O14B—C15B—C16D	145.8 (10)
C11A—O14A—C15A—C16A	−171.0 (3)	C11B—O14B—C15B—C16B	−174.4 (2)
C15C—O14A—C15A—C16A	101.0 (15)	O14B—C15B—C16B—C17B	−74.7 (3)
O14A—C15A—C16A—C17A	−62.0 (7)	C16D—C15B—C16B—C17B	15.3 (15)
C15A—C16A—C17A—C18A	−177.0 (5)	C15B—C16B—C17B—C18B	−170.5 (3)
C11A—O14A—C15C—C16C	166.2 (7)	O14B—C15B—C16D—C17D	139 (2)
C15A—O14A—C15C—C16C	−88.3 (16)	C16B—C15B—C16D—C17D	36.7 (15)
O14A—C15C—C16C—C17C	50.3 (14)	C15B—C16D—C17D—C18D	−130 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O7Ai	0.93 (3)	2.00 (2)	2.864 (2)	154 (2)
N1B—H1B···O7Bii	0.88 (3)	2.06 (2)	2.834 (3)	146 (2)
C9B—H9B···O7Ai	0.93	2.59	3.426 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯O7Ai	0.93 (3)	2.00 (2)	2.864 (2)	154 (2)
N1B—H1B⋯O7Bii	0.88 (3)	2.06 (2)	2.834 (3)	146 (2)
C9B—H9B⋯O7Ai	0.93	2.59	3.426 (3)	149

Symmetry codes: (i) ; (ii) .