2-Meth­oxy-N-[2-(3-thien­yl)-1,2,3,4-tetra­hydro-1-naphth­yl]acetamide

The asymmetric unit of the title compound, C₁₇H₁₉NO₂S, contains two independent mol­ecules with different conformations. Both mol­ecules are linked by inter­molecular N—H...O hydrogen bonds [N...O = 3.033 (4) and 2.969 (4) Å] to form two types of one-dimensional chains running in the b direction.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.059
• wR factor = 0.158
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.619     0.993
            Tmin(prime) and Tmax expected:      0.957     0.989
            RR(prime) =      0.644
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.64

Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12

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           27.49
           From the CIF: _reflns_number_total               6434
           Count of symmetry unique reflns         3738
           Completeness (_total/calc)            172.12%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2696
           Fraction of Friedel pairs measured     0.721
           Are heavy atom types Z>Si present        yes

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

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Computing details

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2001); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC.

2-Methoxy-N-[2-(3-thienyl)-1,2,3,4-tetrahydro-1-naphthyl)acetamide

Crystal data

C17H19NO2S	F(000) = 640
Mr = 301.39	Dx = 1.304 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 12544 reflections
a = 10.5344 (3) Å	θ = 2.6–27.5°
b = 9.7241 (4) Å	µ = 0.22 mm^−1
c = 15.1999 (6) Å	T = 150 K
β = 99.594 (2)°	Needle, colourless
V = 1535.2 (1) Å^3	0.20 × 0.08 × 0.05 mm
Z = 4

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer	6434 independent reflections
Radiation source: fine-focus sealed tube	4012 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 2.6°
φ scans, and ω scans with κ offsets	h = −13→13
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −12→11
Tmin = 0.619, Tmax = 0.993	l = −18→19
12544 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.059	w = 1/[σ^2(Fo^2) + (0.0723P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.158	(Δ/σ)max = 0.001
S = 1.01	Δρmax = 0.25 e Å^−3
6434 reflections	Δρmin = −0.32 e Å^−3
382 parameters	Extinction correction: SHELXTL/PC (Sheldrick, 2001), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.012 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 2710 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.07 (9)

Special details

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
S1A	0.15600 (13)	0.63424 (14)	0.21214 (8)	0.0524 (4)
O1A	−0.0399 (3)	0.6187 (3)	0.55160 (18)	0.0346 (6)
O2A	−0.2062 (2)	0.3489 (3)	0.42352 (18)	0.0366 (7)
N1A	0.0282 (3)	0.4227 (3)	0.4912 (2)	0.0284 (7)
H1NA	0.0034	0.3482	0.4602	0.034*
C1A	0.1745 (4)	0.4946 (5)	0.2817 (3)	0.0437 (11)
H1A	0.1661	0.4021	0.2613	0.052*
C2A	0.2024 (4)	0.5305 (4)	0.3692 (3)	0.0297 (9)
C3A	0.2074 (4)	0.6759 (4)	0.3792 (3)	0.0395 (10)
H3AA	0.2252	0.7206	0.4354	0.047*
C4A	0.1839 (4)	0.7446 (5)	0.3000 (3)	0.0430 (11)
H4A	0.1832	0.8419	0.2946	0.052*
C5A	0.2410 (3)	0.4290 (4)	0.4440 (3)	0.0303 (9)
H5AA	0.2270	0.3341	0.4190	0.036*
C6A	0.1657 (3)	0.4434 (4)	0.5219 (2)	0.0279 (9)
H6AA	0.1777	0.5397	0.5447	0.033*
C7A	0.2180 (4)	0.3468 (4)	0.5990 (3)	0.0297 (9)
C8A	0.1380 (4)	0.3064 (4)	0.6588 (3)	0.0340 (10)
H8AA	0.0515	0.3382	0.6503	0.041*
C9A	0.1820 (4)	0.2204 (5)	0.7306 (3)	0.0402 (11)
H9AA	0.1253	0.1915	0.7695	0.048*
C10A	0.3095 (4)	0.1773 (5)	0.7451 (3)	0.0424 (11)
H10A	0.3417	0.1214	0.7951	0.051*
C11A	0.3894 (4)	0.2169 (4)	0.6855 (3)	0.0365 (10)
H11A	0.4766	0.1874	0.6954	0.044*
C12A	0.3446 (4)	0.2988 (4)	0.6114 (3)	0.0326 (9)
C13A	0.4326 (4)	0.3275 (5)	0.5448 (3)	0.0402 (11)
H13A	0.4399	0.2435	0.5092	0.048*
H13B	0.5195	0.3499	0.5774	0.048*
C14A	0.3851 (3)	0.4458 (4)	0.4820 (3)	0.0363 (10)
H14A	0.4351	0.4481	0.4324	0.044*
H14B	0.3989	0.5340	0.5147	0.044*
C15A	−0.0619 (4)	0.5111 (4)	0.5079 (3)	0.0276 (9)
C16A	−0.1987 (4)	0.4760 (4)	0.4694 (3)	0.0321 (9)
H16A	−0.2504	0.4709	0.5180	0.039*
H16B	−0.2354	0.5495	0.4277	0.039*
C17A	−0.3313 (4)	0.3197 (5)	0.3759 (3)	0.0406 (11)
H17A	−0.3276	0.2379	0.3387	0.061*
H17B	−0.3622	0.3982	0.3379	0.061*
H17C	−0.3902	0.3028	0.4183	0.061*
S1B	0.21885 (10)	0.55950 (13)	−0.18692 (8)	0.0455 (3)
O1B	0.5254 (3)	0.6701 (3)	0.05223 (18)	0.0334 (6)
O2B	0.6502 (2)	0.9329 (3)	−0.07579 (19)	0.0372 (7)
N1B	0.4512 (3)	0.8867 (3)	0.01590 (19)	0.0250 (7)
H1NB	0.4703	0.9671	−0.0050	0.030*
C1B	0.2565 (4)	0.6570 (5)	−0.0931 (3)	0.0360 (10)
H1B	0.3057	0.6242	−0.0391	0.043*
C2B	0.2086 (4)	0.7867 (4)	−0.1038 (3)	0.0310 (9)
C3B	0.1390 (4)	0.8049 (5)	−0.1927 (3)	0.0400 (11)
H3BA	0.0983	0.8887	−0.2134	0.048*
C4B	0.1372 (4)	0.6912 (5)	−0.2441 (3)	0.0454 (12)
H4B	0.0956	0.6856	−0.3044	0.054*
C5B	0.2158 (3)	0.8949 (4)	−0.0320 (3)	0.0290 (9)
H5BA	0.2300	0.9859	−0.0595	0.035*
C6B	0.3268 (3)	0.8712 (4)	0.0460 (2)	0.0270 (9)
H6BA	0.3209	0.7735	0.0654	0.032*
C7B	0.3187 (3)	0.9614 (4)	0.1274 (2)	0.0262 (8)
C8B	0.4263 (4)	0.9715 (4)	0.1939 (3)	0.0318 (9)
H8BA	0.5039	0.9268	0.1863	0.038*
C9B	0.4219 (4)	1.0454 (5)	0.2709 (3)	0.0391 (10)
H9BA	0.4967	1.0529	0.3152	0.047*
C10B	0.3094 (4)	1.1081 (5)	0.2836 (3)	0.0426 (11)
H10B	0.3053	1.1567	0.3373	0.051*
C11B	0.2024 (4)	1.0998 (4)	0.2178 (3)	0.0379 (10)
H11B	0.1252	1.1440	0.2269	0.045*
C12B	0.2039 (4)	1.0286 (4)	0.1383 (3)	0.0311 (9)
C13B	0.0869 (4)	1.0240 (5)	0.0668 (3)	0.0406 (11)
H13C	0.0821	1.1102	0.0318	0.049*
H13D	0.0090	1.0188	0.0952	0.049*
C14B	0.0879 (4)	0.9022 (5)	0.0039 (3)	0.0370 (10)
H14C	0.0158	0.9113	−0.0466	0.044*
H14D	0.0753	0.8160	0.0360	0.044*
C15B	0.5370 (3)	0.7849 (4)	0.0185 (3)	0.0289 (9)
C16B	0.6563 (4)	0.8142 (4)	−0.0220 (3)	0.0352 (10)
H16C	0.7305	0.8234	0.0270	0.042*
H16D	0.6730	0.7339	−0.0585	0.042*
C17B	0.5727 (4)	0.9128 (6)	−0.1611 (3)	0.0479 (12)
H17D	0.5686	0.9986	−0.1953	0.072*
H17E	0.4856	0.8857	−0.1534	0.072*
H17F	0.6106	0.8403	−0.1933	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0681 (8)	0.0476 (8)	0.0442 (7)	0.0100 (6)	0.0169 (6)	0.0117 (6)
O1A	0.0401 (15)	0.0233 (16)	0.0399 (16)	0.0042 (12)	0.0051 (12)	−0.0030 (14)
O2A	0.0293 (15)	0.0334 (18)	0.0457 (17)	−0.0009 (12)	0.0020 (13)	−0.0122 (14)
N1A	0.0287 (16)	0.0223 (18)	0.0344 (18)	−0.0038 (14)	0.0059 (13)	−0.0027 (15)
C1A	0.055 (3)	0.034 (3)	0.043 (3)	0.001 (2)	0.011 (2)	−0.002 (2)
C2A	0.0286 (19)	0.027 (2)	0.036 (2)	0.0024 (16)	0.0102 (16)	0.0018 (18)
C3A	0.042 (2)	0.031 (3)	0.047 (3)	−0.0008 (19)	0.012 (2)	0.000 (2)
C4A	0.049 (3)	0.026 (3)	0.057 (3)	0.005 (2)	0.018 (2)	0.003 (2)
C5A	0.036 (2)	0.020 (2)	0.036 (2)	0.0015 (17)	0.0090 (17)	−0.0002 (17)
C6A	0.0279 (18)	0.021 (2)	0.035 (2)	0.0007 (16)	0.0047 (16)	−0.0012 (17)
C7A	0.033 (2)	0.023 (2)	0.032 (2)	−0.0021 (17)	0.0021 (17)	−0.0054 (17)
C8A	0.035 (2)	0.033 (3)	0.034 (2)	−0.0048 (18)	0.0052 (18)	−0.0002 (19)
C9A	0.051 (3)	0.036 (3)	0.033 (2)	−0.007 (2)	0.007 (2)	0.000 (2)
C10A	0.055 (3)	0.034 (3)	0.033 (2)	−0.007 (2)	−0.008 (2)	0.000 (2)
C11A	0.039 (2)	0.025 (2)	0.042 (2)	−0.0031 (18)	−0.0017 (19)	−0.002 (2)
C12A	0.038 (2)	0.023 (2)	0.036 (2)	−0.0040 (17)	0.0020 (17)	−0.0059 (19)
C13A	0.038 (2)	0.038 (3)	0.045 (3)	0.0046 (19)	0.0084 (19)	0.004 (2)
C14A	0.031 (2)	0.031 (3)	0.049 (3)	0.0052 (18)	0.0125 (19)	0.007 (2)
C15A	0.034 (2)	0.021 (2)	0.029 (2)	0.0019 (17)	0.0077 (16)	0.0025 (17)
C16A	0.035 (2)	0.027 (2)	0.032 (2)	0.0023 (17)	0.0003 (17)	−0.0032 (18)
C17A	0.027 (2)	0.045 (3)	0.049 (3)	−0.0061 (19)	0.0012 (19)	−0.005 (2)
S1B	0.0432 (6)	0.0474 (8)	0.0451 (7)	−0.0058 (5)	0.0047 (5)	−0.0143 (6)
O1B	0.0404 (15)	0.0215 (16)	0.0370 (15)	−0.0003 (12)	0.0027 (12)	0.0008 (13)
O2B	0.0372 (15)	0.0302 (18)	0.0462 (18)	−0.0027 (13)	0.0125 (13)	0.0018 (14)
N1B	0.0290 (16)	0.0164 (17)	0.0311 (17)	−0.0009 (13)	0.0090 (13)	−0.0003 (13)
C1B	0.038 (2)	0.037 (3)	0.031 (2)	0.0017 (19)	−0.0005 (18)	−0.005 (2)
C2B	0.031 (2)	0.032 (2)	0.029 (2)	−0.0035 (18)	0.0022 (16)	0.0014 (19)
C3B	0.036 (2)	0.048 (3)	0.034 (2)	−0.002 (2)	0.0013 (18)	0.009 (2)
C4B	0.042 (2)	0.064 (4)	0.030 (2)	−0.011 (2)	0.0028 (19)	−0.003 (2)
C5B	0.028 (2)	0.025 (2)	0.034 (2)	−0.0007 (16)	0.0049 (16)	0.0037 (17)
C6B	0.027 (2)	0.021 (2)	0.034 (2)	−0.0006 (15)	0.0071 (16)	0.0029 (17)
C7B	0.033 (2)	0.017 (2)	0.030 (2)	0.0010 (15)	0.0092 (17)	0.0033 (16)
C8B	0.039 (2)	0.025 (2)	0.033 (2)	0.0004 (17)	0.0091 (18)	−0.0013 (17)
C9B	0.050 (2)	0.031 (3)	0.037 (2)	−0.002 (2)	0.0085 (19)	−0.004 (2)
C10B	0.062 (3)	0.030 (3)	0.040 (3)	−0.001 (2)	0.019 (2)	−0.003 (2)
C11B	0.045 (2)	0.019 (2)	0.055 (3)	0.0006 (18)	0.023 (2)	−0.003 (2)
C12B	0.037 (2)	0.020 (2)	0.039 (2)	−0.0019 (17)	0.0135 (17)	0.0007 (18)
C13B	0.033 (2)	0.037 (3)	0.052 (3)	0.0102 (19)	0.0095 (19)	−0.002 (2)
C14B	0.030 (2)	0.034 (3)	0.046 (3)	0.0016 (18)	0.0041 (18)	0.003 (2)
C15B	0.028 (2)	0.023 (2)	0.034 (2)	0.0003 (16)	0.0015 (16)	−0.0048 (18)
C16B	0.035 (2)	0.026 (2)	0.045 (3)	0.0048 (18)	0.0091 (18)	0.000 (2)
C17B	0.052 (3)	0.057 (3)	0.037 (2)	0.007 (2)	0.017 (2)	−0.003 (2)

Geometric parameters (Å, º)

S1A—C4A	1.700 (5)	S1B—C4B	1.698 (5)
S1A—C1A	1.712 (5)	S1B—C1B	1.703 (4)
O1A—C15A	1.241 (5)	O1B—C15B	1.243 (5)
O2A—C16A	1.415 (4)	O2B—C16B	1.409 (5)
O2A—C17A	1.422 (4)	O2B—C17B	1.426 (5)
N1A—C15A	1.336 (5)	N1B—C15B	1.337 (5)
N1A—C6A	1.460 (5)	N1B—C6B	1.465 (5)
N1A—H1NA	0.88	N1B—H1NB	0.88
C1A—C2A	1.359 (6)	C1B—C2B	1.358 (6)
C1A—H1A	0.95	C1B—H1B	0.95
C2A—C3A	1.422 (6)	C2B—C3B	1.437 (6)
C2A—C5A	1.509 (5)	C2B—C5B	1.509 (5)
C3A—C4A	1.362 (6)	C3B—C4B	1.352 (6)
C3A—H3AA	0.95	C3B—H3BA	0.95
C4A—H4A	0.95	C4B—H4B	0.95
C5A—C6A	1.538 (5)	C5B—C6B	1.537 (5)
C5A—C14A	1.540 (5)	C5B—C14B	1.538 (5)
C5A—H5AA	1.00	C5B—H5BA	1.00
C6A—C7A	1.530 (5)	C6B—C7B	1.530 (5)
C6A—H6AA	1.00	C6B—H6BA	1.00
C7A—C12A	1.395 (5)	C7B—C8B	1.391 (5)
C7A—C8A	1.396 (5)	C7B—C12B	1.409 (5)
C8A—C9A	1.392 (6)	C8B—C9B	1.381 (5)
C8A—H8AA	0.95	C8B—H8BA	0.95
C9A—C10A	1.389 (6)	C9B—C10B	1.375 (6)
C9A—H9AA	0.95	C9B—H9BA	0.95
C10A—C11A	1.389 (6)	C10B—C11B	1.379 (6)
C10A—H10A	0.95	C10B—H10B	0.95
C11A—C12A	1.396 (6)	C11B—C12B	1.395 (6)
C11A—H11A	0.95	C11B—H11B	0.95
C12A—C13A	1.507 (5)	C12B—C13B	1.501 (6)
C13A—C14A	1.525 (6)	C13B—C14B	1.524 (6)
C13A—H13A	0.99	C13B—H13C	0.99
C13A—H13B	0.99	C13B—H13D	0.99
C14A—H14A	0.99	C14B—H14C	0.99
C14A—H14B	0.99	C14B—H14D	0.99
C15A—C16A	1.501 (5)	C15B—C16B	1.515 (5)
C16A—H16A	0.99	C16B—H16C	0.99
C16A—H16B	0.99	C16B—H16D	0.99
C17A—H17A	0.98	C17B—H17D	0.98
C17A—H17B	0.98	C17B—H17E	0.98
C17A—H17C	0.98	C17B—H17F	0.98
C4A—S1A—C1A	91.6 (2)	C4B—S1B—C1B	92.1 (2)
C16A—O2A—C17A	113.3 (3)	C16B—O2B—C17B	112.3 (3)
C15A—N1A—C6A	123.3 (3)	C15B—N1B—C6B	123.4 (3)
C15A—N1A—H1NA	118.3	C15B—N1B—H1NB	118.3
C6A—N1A—H1NA	118.3	C6B—N1B—H1NB	118.3
C2A—C1A—S1A	112.6 (3)	C2B—C1B—S1B	112.8 (3)
C2A—C1A—H1A	123.7	C2B—C1B—H1B	123.6
S1A—C1A—H1A	123.7	S1B—C1B—H1B	123.6
C1A—C2A—C3A	111.0 (4)	C1B—C2B—C3B	110.3 (4)
C1A—C2A—C5A	123.8 (4)	C1B—C2B—C5B	126.0 (4)
C3A—C2A—C5A	124.7 (4)	C3B—C2B—C5B	123.5 (4)
C4A—C3A—C2A	113.3 (4)	C4B—C3B—C2B	113.5 (4)
C4A—C3A—H3AA	123.4	C4B—C3B—H3BA	123.3
C2A—C3A—H3AA	123.4	C2B—C3B—H3BA	123.3
C3A—C4A—S1A	111.5 (4)	C3B—C4B—S1B	111.4 (3)
C3A—C4A—H4A	124.2	C3B—C4B—H4B	124.3
S1A—C4A—H4A	124.2	S1B—C4B—H4B	124.3
C2A—C5A—C6A	114.4 (3)	C2B—C5B—C6B	113.2 (3)
C2A—C5A—C14A	109.8 (3)	C2B—C5B—C14B	110.3 (3)
C6A—C5A—C14A	107.7 (3)	C6B—C5B—C14B	109.4 (3)
C2A—C5A—H5AA	108.3	C2B—C5B—H5BA	107.9
C6A—C5A—H5AA	108.3	C6B—C5B—H5BA	107.9
C14A—C5A—H5AA	108.3	C14B—C5B—H5BA	107.9
N1A—C6A—C7A	111.8 (3)	N1B—C6B—C7B	111.6 (3)
N1A—C6A—C5A	110.7 (3)	N1B—C6B—C5B	110.4 (3)
C7A—C6A—C5A	111.6 (3)	C7B—C6B—C5B	113.6 (3)
N1A—C6A—H6AA	107.5	N1B—C6B—H6BA	107.0
C7A—C6A—H6AA	107.5	C7B—C6B—H6BA	107.0
C5A—C6A—H6AA	107.5	C5B—C6B—H6BA	107.0
C12A—C7A—C8A	119.0 (4)	C8B—C7B—C12B	119.5 (4)
C12A—C7A—C6A	121.5 (3)	C8B—C7B—C6B	118.7 (3)
C8A—C7A—C6A	119.5 (3)	C12B—C7B—C6B	121.7 (3)
C9A—C8A—C7A	121.4 (4)	C9B—C8B—C7B	121.0 (4)
C9A—C8A—H8AA	119.3	C9B—C8B—H8BA	119.5
C7A—C8A—H8AA	119.3	C7B—C8B—H8BA	119.5
C10A—C9A—C8A	119.5 (4)	C10B—C9B—C8B	120.1 (4)
C10A—C9A—H9AA	120.2	C10B—C9B—H9BA	120.0
C8A—C9A—H9AA	120.2	C8B—C9B—H9BA	120.0
C11A—C10A—C9A	119.2 (4)	C9B—C10B—C11B	119.4 (4)
C11A—C10A—H10A	120.4	C9B—C10B—H10B	120.3
C9A—C10A—H10A	120.4	C11B—C10B—H10B	120.3
C10A—C11A—C12A	121.6 (4)	C10B—C11B—C12B	122.1 (4)
C10A—C11A—H11A	119.2	C10B—C11B—H11B	118.9
C12A—C11A—H11A	119.2	C12B—C11B—H11B	118.9
C7A—C12A—C11A	119.1 (4)	C11B—C12B—C7B	117.8 (4)
C7A—C12A—C13A	121.9 (4)	C11B—C12B—C13B	121.0 (4)
C11A—C12A—C13A	118.9 (4)	C7B—C12B—C13B	121.2 (3)
C12A—C13A—C14A	112.6 (3)	C12B—C13B—C14B	112.8 (3)
C12A—C13A—H13A	109.1	C12B—C13B—H13C	109.0
C14A—C13A—H13A	109.1	C14B—C13B—H13C	109.0
C12A—C13A—H13B	109.1	C12B—C13B—H13D	109.0
C14A—C13A—H13B	109.1	C14B—C13B—H13D	109.0
H13A—C13A—H13B	107.8	H13C—C13B—H13D	107.8
C13A—C14A—C5A	110.8 (3)	C13B—C14B—C5B	110.9 (3)
C13A—C14A—H14A	109.5	C13B—C14B—H14C	109.5
C5A—C14A—H14A	109.5	C5B—C14B—H14C	109.5
C13A—C14A—H14B	109.5	C13B—C14B—H14D	109.5
C5A—C14A—H14B	109.5	C5B—C14B—H14D	109.5
H14A—C14A—H14B	108.1	H14C—C14B—H14D	108.1
O1A—C15A—N1A	124.7 (4)	O1B—C15B—N1B	124.4 (3)
O1A—C15A—C16A	118.8 (3)	O1B—C15B—C16B	118.8 (3)
N1A—C15A—C16A	116.5 (3)	N1B—C15B—C16B	116.8 (3)
O2A—C16A—C15A	111.2 (3)	O2B—C16B—C15B	115.4 (3)
O2A—C16A—H16A	109.4	O2B—C16B—H16C	108.4
C15A—C16A—H16A	109.4	C15B—C16B—H16C	108.4
O2A—C16A—H16B	109.4	O2B—C16B—H16D	108.4
C15A—C16A—H16B	109.4	C15B—C16B—H16D	108.4
H16A—C16A—H16B	108.0	H16C—C16B—H16D	107.5
O2A—C17A—H17A	109.5	O2B—C17B—H17D	109.5
O2A—C17A—H17B	109.5	O2B—C17B—H17E	109.5
H17A—C17A—H17B	109.5	H17D—C17B—H17E	109.5
O2A—C17A—H17C	109.5	O2B—C17B—H17F	109.5
H17A—C17A—H17C	109.5	H17D—C17B—H17F	109.5
H17B—C17A—H17C	109.5	H17E—C17B—H17F	109.5
C6A—C5A—C2A—C1A	−130.6 (4)	C15A—C16A—O2A—C17A	−172.1 (3)
C6B—C5B—C2B—C1B	23.4 (5)	C15B—C16B—O2B—C17B	−75.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O2A	0.88	2.19	2.613 (4)	109
N1B—H1NB···O2B	0.88	2.35	2.741 (4)	107
N1A—H1NA···O1A^i	0.88	2.28	3.033 (4)	144
N1B—H1NB···O1B^ii	0.88	2.10	2.969 (4)	168
C1B—H1B···O2B^iii	0.95	2.54	3.386 (5)	148
C3A—H3AA···O2A^iv	0.95	2.52	3.441 (5)	164
C4B—H4B···O1A^v	0.95	2.49	3.419 (5)	165
C10A—H10A···O1B^vi	0.95	2.55	3.276 (5)	134

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