Crystal structure of N-[(morpholin-4-yl)(thio­phen-2-yl)meth­yl]benzamide

Prabhu, S.A.; Suresh, M.; Jameel, A.A.; Padusha, M.S.A.; Gunasekaran, B.

doi:10.1107/S2056989015011639

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o498-o499

doi:10.1107/S2056989015011639

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Crystal structure of N-[(morpholin-4-yl)(thiophen-2-yl)methyl]benzamide

S. Arun Prabhu,^a M. Suresh,^b A. Abdul Jameel,^c M. Syed Ali Padusha ^b and B. Gunasekaran ^d ^*

^aDepartment of Chemistry, National College, Tiruchirappalli 620 001, Tamil Nadu, India, ^bPG and Research Dept of Chemistry, Jamal Mohamed College (Autonomous), Tiruchirappalli, Tamil Nadu 620 001, India, ^cSri Arumugam Group of Institutions, Tholudhur, Tamil Nadu, India, and ^dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203 Tamil Nadu, India
^*Correspondence e-mail: phdguna@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 14 June 2015; accepted 16 June 2015; online 20 June 2015)

In the title compound, C₁₆H₁₈N₂O₂S, the morpholine ring adopts a chair conformation. The thiophene ring makes a dihedral angle of 63.54 (14)° with the mean plane of the four C atoms [maximum deviation = 0.010 (3) Å] of the morpholine ring. The benzamide ring is disordered, with four C atoms occupying two sets of sites, with a refined occupancy ratio of 0.502 (4):0.498 (4). These two rings are inclined to one another by 85.2 (4)° and to the thiophene ring by 72.7 (3) and 13.0 (3)° for the major and minor components, respectively. In the crystal, molecules are linked via N—H⋯O hydrogen bonds, forming chains along [001].

Keywords: crystal structure; benzamide; morpholino; thiophene; hydrogen bonding.

CCDC reference: 1406913

1. Related literature

For the biological activity of benzamide derivatives, see: Carbonnelle et al. (2005 ); Hatzelmann & Schudt (2001 ); Simonini et al. (2006 ); Suzuki et al. (2005 ); Zhou et al. (1999 ); For related structures see: Muruganandam et al. (2009 ); Khan et al. (2012 ).

2. Experimental

2.1. Crystal data

C₁₆H₁₈N₂O₂S
M_r = 302.38
Monoclinic, P 2₁ /c
a = 16.5283 (11) Å
b = 9.9049 (7) Å
c = 9.6831 (5) Å
β = 99.056 (2)°
V = 1565.47 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 295 K
0.40 × 0.30 × 0.20 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.920, T_max = 0.959
11905 measured reflections
3836 independent reflections
2744 reflections with I > 2σ(I)
R_int = 0.024

2.3. Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.182
S = 1.04
3836 reflections
227 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.02	2.878 (2)	173
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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

Supporting information

CCDC reference: 1406913

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015011639/su5156sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015011639/su5156Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015011639/su5156Isup3.cml

checkCIF report

Synthesis and crystallization top

To an alkaline solution of benzamide (0.025 mol, 3.03 g), morpholine (0.025 mol, 2.2 ml) was added drop wise in ice cold conditions and the contents were stirred for 5 min. Thiophene-2-aldehyde (0.025 mol, 2.3 ml) was then added drop wise and stirring was continued for 1 h. The Mannich base product formed was filtered, washed with water and recrystallized with ethanol (yield: 75%; m.p.: 433 K) giving colourless block-like crystals.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. Four C atoms in the benzamide ring (C2/C2A, C3/C3A, C5/C5A, and C6/C6A) are disordered over two positions with a refined occupany ratio of 0.502 (5):0.48 (5). All of the H atoms were positioned geometrically and refined using a riding model: N—H = 0.86 Å, C—H = 0.93 - 0.98 Å with U_iso(H) = 1.2U_eq(N,C).

Comment top

Benzamide and its derivatives, have recently received great attention because of their wide range of pharmacological activities, such as anti-inflammatory, immunomodulatory (Hatzelmann & Schudt, 2001; Carbonnelle et al., 2005), anti-tumoral (Suzuki et al., 2005), antipsychotic (Simonini et al., 2006), and antiallergic (Zhou et al., 1999).

The geometric parameters of the title compound (Fig. 1) agree well with those reported for similar structures (Muruganandam et al., 2009; Khan et al., 2012). The morpholine ring adopts a chair conformation. The thiophene ring makes a dihedral angle of 63.54 (14) ° with the mean plane of the four C atoms (maximum deviation 0.010 (3) Å) of the morpholine ring. The benzamide ring is disordered with four C atoms occupying two positions, with a refined occupancy ratio of 0.502 (5):0.498 (5). These two rings are inclined to one another by 85.2 (4) ° and to the thiophene ring by 72.7 (3) and 13.0 (3) °, for the major and minor component, respectively.

In the crystal, molecules are linked via N—H···O hydrogen bonds forming chains along [001]; see Table 1 and Fig. 2

Related literature top

For the biological activity of benzamide derivatives, see: Carbonnelle et al. (2005); Hatzelmann & Schudt (2001); Simonini et al. (2006); Suzuki et al. (2005); Zhou et al. (1999); For related structures see: Muruganandam et al. (2009); Khan et al. (2012).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The minor component of the disordered benzamide ring is shown with dashed lines.
	Fig. 2. A view along the b axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details). The C-bound H atoms and the minor component of the disordered benzamide ring have been omitted for clarity.

N-[(Morpholin-4-yl)(thiophen-2-yl)methyl]benzamide top

Crystal data top

C₁₆H₁₈N₂O₂S	F(000) = 640
M_r = 302.38	D_x = 1.283 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3836 reflections
a = 16.5283 (11) Å	θ = 2.4–28.3°
b = 9.9049 (7) Å	µ = 0.21 mm⁻¹
c = 9.6831 (5) Å	T = 295 K
β = 99.056 (2)°	Block, colourless
V = 1565.47 (17) Å³	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3836 independent reflections
Radiation source: fine-focus sealed tube	2744 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 0 pixels mm^-1	θ_max = 28.3°, θ_min = 2.4°
ω and ϕ scans	h = −21→21
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
T_min = 0.920, T_max = 0.959	l = −12→7
11905 measured reflections

Refinement top

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.097P)² + 0.5504P] where P = (F_o² + 2F_c²)/3
3836 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.62 e Å⁻³
1 restraint	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₆H₁₈N₂O₂S	V = 1565.47 (17) Å³
M_r = 302.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.5283 (11) Å	µ = 0.21 mm⁻¹
b = 9.9049 (7) Å	T = 295 K
c = 9.6831 (5) Å	0.40 × 0.30 × 0.20 mm
β = 99.056 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3836 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2744 reflections with I > 2σ(I)
T_min = 0.920, T_max = 0.959	R_int = 0.024
11905 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	1 restraint
wR(F²) = 0.182	H-atom parameters constrained
S = 1.04	Δρ_max = 0.62 e Å⁻³
3836 reflections	Δρ_min = −0.41 e Å⁻³
227 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.94818 (4)	0.28631 (7)	0.23066 (8)	0.0622 (3)
N2	0.81748 (10)	0.05848 (16)	0.16552 (16)	0.0345 (4)
O2	0.81001 (12)	−0.19318 (16)	0.0245 (2)	0.0610 (5)
O1	0.66536 (11)	0.2032 (3)	0.37090 (16)	0.0734 (7)
N1	0.70424 (10)	0.21935 (18)	0.16023 (16)	0.0365 (4)
H1	0.6897	0.2365	0.0728	0.044*
C14	0.82300 (13)	0.4243 (2)	0.1121 (2)	0.0406 (5)
H14	0.7698	0.4523	0.0784	0.049*
C7	0.64812 (12)	0.2222 (2)	0.2448 (2)	0.0402 (5)
C1	0.56136 (13)	0.2450 (2)	0.1788 (2)	0.0450 (5)
C2	0.5166 (4)	0.3348 (8)	0.2408 (8)	0.087 (2)	0.502 (4)
H2	0.5404	0.3854	0.3174	0.105*	0.502 (4)
C6	0.5297 (3)	0.1744 (7)	0.0642 (6)	0.0662 (16)	0.502 (4)
H6	0.5626	0.1187	0.0192	0.079*	0.502 (4)
C2A	0.5393 (3)	0.3477 (7)	0.0839 (7)	0.0745 (18)	0.498 (4)
H2A	0.5798	0.4024	0.0570	0.089*	0.498 (4)
C6A	0.4971 (4)	0.1642 (9)	0.2132 (8)	0.093 (3)	0.498 (4)
H6A	0.5096	0.0944	0.2772	0.112*	0.498 (4)
C15	0.89612 (15)	0.5008 (2)	0.1046 (3)	0.0502 (5)
H15	0.8954	0.5852	0.0624	0.060*
C13	0.84490 (11)	0.29981 (19)	0.1788 (2)	0.0342 (4)
C8	0.79002 (11)	0.1877 (2)	0.21266 (19)	0.0329 (4)
H8	0.7955	0.1831	0.3148	0.039*
C16	0.96545 (15)	0.4401 (2)	0.1637 (3)	0.0570 (6)
H16	1.0172	0.4781	0.1676	0.068*
C9	0.81880 (14)	0.0498 (2)	0.0153 (2)	0.0432 (5)
H9A	0.8509	0.1235	−0.0138	0.052*
H9B	0.7635	0.0569	−0.0355	0.052*
C10	0.85569 (17)	−0.0830 (2)	−0.0167 (3)	0.0549 (6)
H10A	0.8572	−0.0888	−0.1163	0.066*
H10B	0.9116	−0.0881	0.0319	0.066*
C12	0.77106 (14)	−0.0547 (2)	0.2094 (2)	0.0463 (5)
H12A	0.7143	−0.0484	0.1649	0.056*
H12B	0.7725	−0.0516	0.3098	0.056*
C11	0.80761 (16)	−0.1865 (2)	0.1691 (3)	0.0557 (6)
H11A	0.8628	−0.1956	0.2200	0.067*
H11B	0.7753	−0.2612	0.1955	0.067*
C4	0.3980 (2)	0.2798 (6)	0.0732 (5)	0.1096 (16)
H4	0.3428	0.2933	0.0388	0.132*
C3	0.4339 (4)	0.3488 (11)	0.1858 (11)	0.114 (3)	0.502 (4)
H3	0.4023	0.4084	0.2289	0.137*	0.502 (4)
C5	0.4464 (4)	0.1872 (11)	0.0152 (8)	0.106 (3)	0.502 (4)
H5	0.4224	0.1326	−0.0580	0.127*	0.502 (4)
C3A	0.4572 (4)	0.3710 (10)	0.0275 (8)	0.101 (3)	0.498 (4)
H3A	0.4416	0.4407	−0.0354	0.121*	0.498 (4)
C5A	0.4167 (4)	0.1852 (13)	0.1551 (11)	0.114 (3)	0.498 (4)
H5A	0.3762	0.1279	0.1777	0.136*	0.498 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0364 (3)	0.0508 (4)	0.0969 (6)	−0.0011 (2)	0.0025 (3)	0.0151 (3)
N2	0.0359 (8)	0.0349 (8)	0.0319 (8)	−0.0025 (6)	0.0033 (6)	0.0022 (6)
O2	0.0749 (12)	0.0380 (9)	0.0652 (11)	0.0012 (8)	−0.0042 (9)	−0.0067 (7)
O1	0.0502 (10)	0.142 (2)	0.0284 (8)	0.0135 (11)	0.0070 (7)	−0.0040 (9)
N1	0.0306 (8)	0.0520 (10)	0.0258 (7)	0.0022 (7)	0.0014 (6)	0.0014 (7)
C14	0.0478 (10)	0.0426 (11)	0.0307 (9)	−0.0071 (8)	0.0041 (8)	−0.0024 (8)
C7	0.0352 (10)	0.0549 (12)	0.0300 (9)	−0.0002 (8)	0.0039 (7)	−0.0081 (8)
C1	0.0327 (10)	0.0642 (14)	0.0385 (10)	0.0004 (9)	0.0069 (8)	−0.0069 (10)
C2	0.046 (3)	0.120 (6)	0.096 (5)	0.021 (3)	0.013 (3)	−0.035 (4)
C6	0.038 (2)	0.097 (4)	0.062 (3)	−0.006 (2)	0.000 (2)	−0.020 (3)
C2A	0.050 (3)	0.085 (4)	0.086 (4)	0.016 (3)	0.004 (3)	0.003 (3)
C6A	0.046 (3)	0.141 (7)	0.091 (5)	−0.020 (4)	0.006 (3)	0.019 (5)
C15	0.0563 (12)	0.0358 (11)	0.0592 (13)	−0.0036 (9)	0.0115 (11)	0.0041 (10)
C13	0.0313 (9)	0.0365 (10)	0.0339 (9)	0.0006 (7)	0.0029 (7)	−0.0036 (7)
C8	0.0297 (8)	0.0420 (10)	0.0261 (8)	0.0008 (7)	0.0019 (7)	0.0001 (7)
C16	0.0446 (12)	0.0454 (13)	0.0821 (18)	−0.0088 (10)	0.0136 (11)	0.0029 (12)
C9	0.0565 (12)	0.0396 (11)	0.0332 (10)	0.0059 (9)	0.0061 (9)	0.0000 (8)
C10	0.0717 (16)	0.0452 (13)	0.0471 (12)	0.0089 (11)	0.0072 (11)	−0.0057 (10)
C12	0.0441 (11)	0.0448 (12)	0.0488 (12)	−0.0082 (9)	0.0039 (9)	0.0100 (9)
C11	0.0565 (14)	0.0397 (12)	0.0677 (16)	−0.0052 (10)	−0.0004 (12)	0.0114 (11)
C4	0.0342 (15)	0.188 (5)	0.102 (3)	0.011 (2)	−0.0034 (17)	−0.028 (3)
C3	0.050 (4)	0.155 (9)	0.141 (8)	0.040 (5)	0.027 (4)	−0.010 (6)
C5	0.048 (3)	0.179 (9)	0.082 (5)	−0.027 (4)	−0.018 (3)	−0.008 (5)
C3A	0.072 (4)	0.129 (7)	0.094 (5)	0.047 (5)	−0.010 (4)	0.002 (5)
C5A	0.039 (3)	0.176 (10)	0.122 (7)	−0.020 (5)	0.000 (4)	0.008 (7)

Geometric parameters (Å, º) top

S1—C16	1.697 (2)	C6A—H6A	0.9300
S1—C13	1.7071 (19)	C15—C16	1.340 (3)
N2—C8	1.455 (2)	C15—H15	0.9300
N2—C12	1.459 (2)	C13—C8	1.502 (3)
N2—C9	1.461 (2)	C8—H8	0.9800
O2—C11	1.408 (3)	C16—H16	0.9300
O2—C10	1.420 (3)	C9—C10	1.503 (3)
O1—C7	1.223 (3)	C9—H9A	0.9700
N1—C7	1.331 (3)	C9—H9B	0.9700
N1—C8	1.463 (2)	C10—H10A	0.9700
N1—H1	0.8600	C10—H10B	0.9700
C14—C13	1.413 (3)	C12—C11	1.516 (3)
C14—C15	1.438 (3)	C12—H12A	0.9700
C14—H14	0.9300	C12—H12B	0.9700
C7—C1	1.493 (3)	C11—H11A	0.9700
C1—C6	1.345 (6)	C11—H11B	0.9700
C1—C2	1.356 (6)	C4—C5A	1.235 (11)
C1—C2A	1.380 (7)	C4—C3	1.344 (11)
C1—C6A	1.411 (7)	C4—C5	1.392 (10)
C2—C3	1.394 (9)	C4—C3A	1.451 (11)
C2—H2	0.9300	C4—H4	0.9300
C6—C5	1.391 (7)	C3—H3	0.9300
C6—H6	0.9300	C5—H5	0.9300
C2A—C3A	1.400 (8)	C3A—H3A	0.9300
C2A—H2A	0.9300	C5A—H5A	0.9300
C6A—C5A	1.375 (10)

C16—S1—C13	92.16 (11)	C15—C16—H16	123.8
C8—N2—C12	112.35 (15)	S1—C16—H16	123.8
C8—N2—C9	114.73 (15)	N2—C9—C10	109.09 (17)
C12—N2—C9	109.61 (16)	N2—C9—H9A	109.9
C11—O2—C10	110.06 (18)	C10—C9—H9A	109.9
C7—N1—C8	121.48 (15)	N2—C9—H9B	109.9
C7—N1—H1	119.3	C10—C9—H9B	109.9
C8—N1—H1	119.3	H9A—C9—H9B	108.3
C13—C14—C15	109.02 (19)	O2—C10—C9	111.3 (2)
C13—C14—H14	125.5	O2—C10—H10A	109.4
C15—C14—H14	125.5	C9—C10—H10A	109.4
O1—C7—N1	122.37 (19)	O2—C10—H10B	109.4
O1—C7—C1	120.54 (19)	C9—C10—H10B	109.4
N1—C7—C1	117.06 (17)	H10A—C10—H10B	108.0
C6—C1—C2	122.5 (4)	N2—C12—C11	109.75 (18)
C6—C1—C2A	78.9 (4)	N2—C12—H12A	109.7
C2—C1—C2A	72.9 (5)	C11—C12—H12A	109.7
C6—C1—C6A	72.0 (4)	N2—C12—H12B	109.7
C2—C1—C6A	77.6 (5)	C11—C12—H12B	109.7
C2A—C1—C6A	116.5 (4)	H12A—C12—H12B	108.2
C6—C1—C7	119.8 (3)	O2—C11—C12	111.78 (19)
C2—C1—C7	117.6 (3)	O2—C11—H11A	109.3
C2A—C1—C7	122.2 (3)	C12—C11—H11A	109.3
C6A—C1—C7	121.4 (4)	O2—C11—H11B	109.3
C1—C2—C3	117.8 (7)	C12—C11—H11B	109.3
C1—C2—H2	121.1	H11A—C11—H11B	107.9
C3—C2—H2	121.1	C5A—C4—C3	80.2 (7)
C1—C6—C5	118.0 (6)	C5A—C4—C5	70.0 (7)
C1—C6—H6	121.0	C3—C4—C5	117.0 (5)
C5—C6—H6	121.0	C5A—C4—C3A	123.7 (5)
C1—C2A—C3A	121.3 (6)	C3—C4—C3A	72.4 (6)
C1—C2A—H2A	119.4	C5—C4—C3A	80.2 (5)
C3A—C2A—H2A	119.4	C5A—C4—H4	118.1
C5A—C6A—C1	122.2 (7)	C3—C4—H4	120.1
C5A—C6A—H6A	118.9	C5—C4—H4	123.0
C1—C6A—H6A	118.9	C3A—C4—H4	118.1
C16—C15—C14	114.3 (2)	C4—C3—C2	122.8 (7)
C16—C15—H15	122.8	C4—C3—H3	118.6
C14—C15—H15	122.8	C2—C3—H3	118.6
C14—C13—C8	128.68 (17)	C6—C5—C4	121.6 (6)
C14—C13—S1	112.05 (15)	C6—C5—H5	119.2
C8—C13—S1	119.20 (14)	C4—C5—H5	119.2
N2—C8—N1	114.37 (15)	C2A—C3A—C4	115.9 (7)
N2—C8—C13	110.65 (14)	C2A—C3A—H3A	122.0
N1—C8—C13	110.57 (16)	C4—C3A—H3A	122.0
N2—C8—H8	106.9	C4—C5A—C6A	120.4 (8)
N1—C8—H8	106.9	C4—C5A—H5A	119.8
C13—C8—H8	106.9	C6A—C5A—H5A	119.8
C15—C16—S1	112.44 (18)

C8—N1—C7—O1	2.6 (3)	C9—N2—C8—C13	−59.9 (2)
C8—N1—C7—C1	−175.38 (18)	C7—N1—C8—N2	111.0 (2)
O1—C7—C1—C6	−130.9 (4)	C7—N1—C8—C13	−123.3 (2)
N1—C7—C1—C6	47.1 (4)	C14—C13—C8—N2	130.5 (2)
O1—C7—C1—C2	47.1 (5)	S1—C13—C8—N2	−52.7 (2)
N1—C7—C1—C2	−134.9 (5)	C14—C13—C8—N1	2.7 (3)
O1—C7—C1—C2A	133.5 (4)	S1—C13—C8—N1	179.57 (13)
N1—C7—C1—C2A	−48.5 (4)	C14—C15—C16—S1	0.7 (3)
O1—C7—C1—C6A	−44.8 (5)	C13—S1—C16—C15	0.3 (2)
N1—C7—C1—C6A	133.1 (5)	C8—N2—C9—C10	174.63 (17)
C6—C1—C2—C3	2.8 (10)	C12—N2—C9—C10	−57.9 (2)
C2A—C1—C2—C3	67.0 (8)	C11—O2—C10—C9	−59.3 (3)
C6A—C1—C2—C3	−56.0 (8)	N2—C9—C10—O2	59.6 (3)
C7—C1—C2—C3	−175.2 (6)	C8—N2—C12—C11	−174.71 (17)
C2—C1—C6—C5	−5.1 (9)	C9—N2—C12—C11	56.5 (2)
C2A—C1—C6—C5	−66.4 (7)	C10—O2—C11—C12	57.7 (3)
C6A—C1—C6—C5	56.4 (7)	N2—C12—C11—O2	−56.9 (2)
C7—C1—C6—C5	172.8 (5)	C5A—C4—C3—C2	64.2 (10)
C6—C1—C2A—C3A	64.4 (7)	C5—C4—C3—C2	2.7 (14)
C2—C1—C2A—C3A	−65.0 (7)	C3A—C4—C3—C2	−66.0 (10)
C6A—C1—C2A—C3A	1.1 (9)	C1—C2—C3—C4	−1.6 (14)
C7—C1—C2A—C3A	−177.3 (5)	C1—C6—C5—C4	6.3 (11)
C6—C1—C6A—C5A	−66.7 (8)	C5A—C4—C5—C6	−72.3 (9)
C2—C1—C6A—C5A	63.9 (9)	C3—C4—C5—C6	−5.1 (12)
C2A—C1—C6A—C5A	0.4 (10)	C3A—C4—C5—C6	59.2 (8)
C7—C1—C6A—C5A	178.9 (7)	C1—C2A—C3A—C4	−1.0 (10)
C13—C14—C15—C16	−1.6 (3)	C5A—C4—C3A—C2A	−1.0 (11)
C15—C14—C13—C8	178.82 (19)	C3—C4—C3A—C2A	63.8 (7)
C15—C14—C13—S1	1.8 (2)	C5—C4—C3A—C2A	−58.7 (7)
C16—S1—C13—C14	−1.24 (17)	C3—C4—C5A—C6A	−58.5 (9)
C16—S1—C13—C8	−178.59 (17)	C5—C4—C5A—C6A	65.1 (9)
C12—N2—C8—N1	−60.4 (2)	C3A—C4—C5A—C6A	2.6 (14)
C9—N2—C8—N1	65.7 (2)	C1—C6A—C5A—C4	−2.3 (14)
C12—N2—C8—C13	173.99 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.02	2.878 (2)	173

Symmetry code: (i) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.02	2.878 (2)	173

Symmetry code: (i) x, −y+1/2, z−1/2.

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Volume 71| Part 7| July 2015| Pages o498-o499

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