2,6-Bis(2-methoxy­phen­yl)-1-nitroso-3,5-diphenyl­piperidin-4-one

The piperidone ring in the title compound, C₃₁H₂₈N₂O₄, adopts the usual twist–boat conformation. The configurations of the aryl rings at the 2- and 3-positions are equatorial and those at the 5- and 6-positions are axial. The crystal structure is characterized by C—H...O and C—H...N hydrogen bonds between centrosymmetrically related pairs of mol­ecules. In addition, there is an intra­molecular C—H...O hydrogen bond and a weak C—H...π inter­action. No significant ar­yl–aryl inter­actions were observed.

Key indicators

• Single-crystal X-ray study
• T = 105 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.035
• wR factor = 0.098
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSMU01_ALERT_1_B  The ratio of given/expected absorption coefficient lies
               outside the range 0.95 <> 1.05
            Calculated value of mu =     0.086
            Value of mu given      =     0.090

Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.05 Ratio

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

   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

2,6-Bis(2-methoxyphenyl)-1-nitroso-3,5-diphenylpiperidin-4-one

Crystal data

C31H28N2O4	F(000) = 1040
Mr = 492.55	Dx = 1.289 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3342 reflections
a = 13.4969 (3) Å	θ = 2–23°
b = 11.7546 (3) Å	µ = 0.09 mm^−1
c = 16.1467 (4) Å	T = 105 K
β = 97.842 (1)°	Block, colourless
V = 2537.73 (11) Å^3	0.28 × 0.14 × 0.12 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	6291 independent reflections
Radiation source: fine-focus sealed tube	5047 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −17→17
Tmin = 0.97, Tmax = 0.99	k = −15→15
39911 measured reflections	l = −21→21

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)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0431P)^2 + 0.6373P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
6291 reflections	Δρmax = 0.31 e Å^−3
337 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0018 (5)

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
O1	0.12069 (6)	0.29495 (6)	0.18681 (5)	0.02893 (18)
O2	−0.03661 (6)	0.63085 (7)	0.41440 (5)	0.03164 (19)
N2	0.11885 (7)	0.39986 (8)	0.17593 (5)	0.02355 (19)
N1	0.09065 (6)	0.45903 (7)	0.23872 (5)	0.01965 (18)
O4	0.04536 (7)	0.22851 (7)	0.42038 (5)	0.0330 (2)
O3	−0.06854 (6)	0.57384 (7)	0.10756 (5)	0.02920 (18)
C3	0.02066 (7)	0.64143 (8)	0.28100 (6)	0.0193 (2)
H3	−0.0457	0.6284	0.2465	0.023*
C4	0.01561 (8)	0.58899 (9)	0.36705 (6)	0.0213 (2)
C2	0.10063 (7)	0.58464 (8)	0.23461 (6)	0.01848 (19)
H2	0.1673	0.6046	0.2662	0.022*
C6	0.07321 (8)	0.39960 (9)	0.31585 (6)	0.0205 (2)
H6	0.1285	0.3432	0.3295	0.025*
C21	0.09995 (8)	0.62842 (8)	0.14603 (6)	0.0209 (2)
C51	0.18252 (8)	0.51814 (9)	0.42986 (6)	0.0213 (2)
C22	0.01479 (8)	0.62599 (9)	0.08531 (6)	0.0237 (2)
C5	0.07763 (8)	0.48247 (8)	0.39015 (6)	0.0203 (2)
H5	0.0461	0.4426	0.4346	0.024*
C31	0.03745 (8)	0.76919 (9)	0.28566 (6)	0.0199 (2)
C26	0.18671 (8)	0.67968 (9)	0.12556 (7)	0.0237 (2)
H26	0.2448	0.6817	0.1661	0.028*
C36	0.12379 (8)	0.81481 (9)	0.33101 (7)	0.0249 (2)
H36	0.1713	0.7659	0.3619	0.030*
C62	−0.03549 (9)	0.24503 (9)	0.36093 (8)	0.0290 (2)
C52	0.26916 (8)	0.50267 (9)	0.39305 (7)	0.0250 (2)
H52	0.2651	0.4688	0.3393	0.030*
C25	0.19021 (9)	0.72794 (9)	0.04712 (7)	0.0294 (2)
H25	0.2501	0.7617	0.0340	0.035*
C32	−0.03129 (8)	0.84239 (10)	0.24165 (7)	0.0268 (2)
H32	−0.0906	0.8123	0.2110	0.032*
C24	0.10507 (10)	0.72583 (10)	−0.01117 (7)	0.0316 (3)
H24	0.1064	0.7595	−0.0645	0.038*
C53	0.36162 (9)	0.53659 (10)	0.43469 (7)	0.0302 (2)
H53	0.4201	0.5270	0.4087	0.036*
C23	0.01772 (9)	0.67535 (10)	0.00704 (7)	0.0293 (2)
H23	−0.0401	0.6744	−0.0337	0.035*
C61	−0.02486 (8)	0.33371 (9)	0.30383 (7)	0.0245 (2)
C33	−0.01456 (10)	0.95930 (10)	0.24172 (8)	0.0331 (3)
H33	−0.0623	1.0084	0.2114	0.040*
C66	−0.10223 (9)	0.35544 (11)	0.24025 (8)	0.0319 (3)
H66	−0.0959	0.4153	0.2018	0.038*
C34	0.07190 (9)	1.00388 (10)	0.28610 (8)	0.0316 (3)
H34	0.0840	1.0835	0.2857	0.038*
C27	−0.15585 (9)	0.56825 (11)	0.04596 (8)	0.0330 (3)
H27A	−0.1805	0.6454	0.0325	0.050*
H27B	−0.2079	0.5240	0.0681	0.050*
H27C	−0.1387	0.5316	−0.0047	0.050*
C56	0.19083 (9)	0.56763 (11)	0.50912 (7)	0.0307 (3)
H56	0.1324	0.5796	0.5348	0.037*
C64	−0.19835 (10)	0.20308 (12)	0.28833 (10)	0.0449 (4)
H64	−0.2575	0.1584	0.2826	0.054*
C55	0.28315 (10)	0.59947 (12)	0.55072 (8)	0.0368 (3)
H55	0.2877	0.6320	0.6050	0.044*
C63	−0.12250 (10)	0.18009 (11)	0.35267 (9)	0.0392 (3)
H63	−0.1297	0.1203	0.3910	0.047*
C54	0.36897 (9)	0.58417 (11)	0.51361 (8)	0.0328 (3)
H54	0.4323	0.6062	0.5422	0.039*
C35	0.14056 (9)	0.93175 (10)	0.33111 (7)	0.0294 (2)
H35	0.1994	0.9623	0.3622	0.035*
C67	0.03830 (13)	0.14268 (11)	0.48228 (9)	0.0449 (3)
H67A	−0.0197	0.1582	0.5110	0.067*
H67B	0.0993	0.1432	0.5229	0.067*
H67C	0.0305	0.0680	0.4552	0.067*
C65	−0.18954 (10)	0.29002 (13)	0.23218 (9)	0.0425 (3)
H65	−0.2424	0.3052	0.1884	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0386 (5)	0.0196 (4)	0.0295 (4)	0.0011 (3)	0.0081 (3)	−0.0040 (3)
O2	0.0399 (5)	0.0292 (4)	0.0295 (4)	0.0051 (4)	0.0179 (4)	−0.0006 (3)
N2	0.0276 (5)	0.0225 (4)	0.0211 (4)	0.0008 (4)	0.0055 (3)	−0.0040 (3)
N1	0.0237 (4)	0.0187 (4)	0.0172 (4)	−0.0009 (3)	0.0049 (3)	−0.0014 (3)
O4	0.0465 (5)	0.0236 (4)	0.0306 (4)	−0.0051 (4)	0.0108 (4)	0.0054 (3)
O3	0.0240 (4)	0.0399 (5)	0.0226 (4)	−0.0011 (3)	−0.0009 (3)	−0.0037 (3)
C3	0.0196 (5)	0.0202 (5)	0.0182 (4)	−0.0002 (4)	0.0029 (4)	−0.0023 (4)
C4	0.0229 (5)	0.0209 (5)	0.0208 (5)	−0.0040 (4)	0.0059 (4)	−0.0033 (4)
C2	0.0213 (5)	0.0175 (5)	0.0169 (4)	−0.0005 (4)	0.0035 (4)	−0.0012 (3)
C6	0.0255 (5)	0.0185 (5)	0.0184 (5)	−0.0018 (4)	0.0065 (4)	−0.0001 (4)
C21	0.0275 (5)	0.0183 (5)	0.0173 (4)	0.0027 (4)	0.0048 (4)	−0.0014 (4)
C51	0.0252 (5)	0.0187 (5)	0.0202 (5)	−0.0016 (4)	0.0038 (4)	0.0016 (4)
C22	0.0277 (5)	0.0231 (5)	0.0204 (5)	0.0037 (4)	0.0037 (4)	−0.0033 (4)
C5	0.0246 (5)	0.0198 (5)	0.0174 (4)	−0.0024 (4)	0.0059 (4)	−0.0011 (4)
C31	0.0232 (5)	0.0200 (5)	0.0173 (4)	0.0012 (4)	0.0063 (4)	−0.0022 (4)
C26	0.0303 (5)	0.0190 (5)	0.0226 (5)	−0.0004 (4)	0.0058 (4)	−0.0014 (4)
C36	0.0247 (5)	0.0234 (5)	0.0263 (5)	0.0007 (4)	0.0028 (4)	−0.0025 (4)
C62	0.0346 (6)	0.0205 (5)	0.0353 (6)	−0.0041 (4)	0.0174 (5)	−0.0068 (4)
C52	0.0279 (5)	0.0260 (5)	0.0214 (5)	0.0026 (4)	0.0047 (4)	0.0028 (4)
C25	0.0410 (7)	0.0219 (5)	0.0277 (6)	−0.0026 (5)	0.0136 (5)	−0.0002 (4)
C32	0.0267 (5)	0.0270 (6)	0.0259 (5)	0.0038 (4)	0.0012 (4)	−0.0014 (4)
C24	0.0516 (7)	0.0242 (5)	0.0201 (5)	0.0049 (5)	0.0087 (5)	0.0023 (4)
C53	0.0241 (5)	0.0333 (6)	0.0335 (6)	0.0020 (5)	0.0056 (4)	0.0069 (5)
C23	0.0384 (6)	0.0286 (6)	0.0201 (5)	0.0079 (5)	0.0007 (4)	−0.0023 (4)
C61	0.0267 (5)	0.0220 (5)	0.0266 (5)	−0.0037 (4)	0.0104 (4)	−0.0069 (4)
C33	0.0394 (7)	0.0254 (6)	0.0345 (6)	0.0098 (5)	0.0051 (5)	0.0033 (5)
C66	0.0282 (6)	0.0340 (6)	0.0344 (6)	−0.0035 (5)	0.0078 (5)	−0.0067 (5)
C34	0.0407 (7)	0.0196 (5)	0.0374 (6)	0.0010 (5)	0.0154 (5)	−0.0033 (4)
C27	0.0263 (6)	0.0382 (7)	0.0321 (6)	0.0053 (5)	−0.0050 (5)	−0.0089 (5)
C56	0.0282 (6)	0.0379 (6)	0.0267 (5)	−0.0041 (5)	0.0070 (4)	−0.0079 (5)
C64	0.0313 (7)	0.0381 (7)	0.0696 (10)	−0.0129 (5)	0.0227 (7)	−0.0155 (7)
C55	0.0355 (7)	0.0432 (7)	0.0307 (6)	−0.0063 (5)	0.0005 (5)	−0.0120 (5)
C63	0.0397 (7)	0.0267 (6)	0.0566 (8)	−0.0082 (5)	0.0262 (6)	−0.0064 (6)
C54	0.0279 (6)	0.0319 (6)	0.0366 (6)	−0.0043 (5)	−0.0032 (5)	0.0019 (5)
C35	0.0289 (6)	0.0257 (5)	0.0346 (6)	−0.0042 (4)	0.0079 (5)	−0.0076 (5)
C67	0.0744 (10)	0.0280 (6)	0.0365 (7)	−0.0047 (6)	0.0227 (7)	0.0080 (5)
C65	0.0262 (6)	0.0506 (8)	0.0508 (8)	−0.0062 (6)	0.0062 (5)	−0.0144 (7)

Geometric parameters (Å, º)

O1—N2	1.2454 (12)	C52—H52	0.9500
O2—C4	1.2126 (13)	C25—C24	1.3828 (17)
N2—N1	1.3272 (12)	C25—H25	0.9500
N1—C6	1.4746 (12)	C32—C33	1.3926 (17)
N1—C2	1.4850 (12)	C32—H32	0.9500
O4—C62	1.3653 (15)	C24—C23	1.3867 (18)
O4—C67	1.4325 (14)	C24—H24	0.9500
O3—C22	1.3712 (14)	C53—C54	1.3827 (17)
O3—C27	1.4361 (13)	C53—H53	0.9500
C3—C31	1.5191 (14)	C23—H23	0.9500
C3—C4	1.5300 (14)	C61—C66	1.3846 (17)
C3—C2	1.5466 (13)	C33—C34	1.3863 (18)
C3—H3	1.0000	C33—H33	0.9500
C4—C5	1.5239 (15)	C66—C65	1.3982 (17)
C2—C21	1.5190 (13)	C66—H66	0.9500
C2—H2	1.0000	C34—C35	1.3864 (17)
C6—C61	1.5230 (14)	C34—H34	0.9500
C6—C5	1.5401 (13)	C27—H27A	0.9800
C6—H6	1.0000	C27—H27B	0.9800
C21—C26	1.3961 (15)	C27—H27C	0.9800
C21—C22	1.4055 (14)	C56—C55	1.3839 (17)
C51—C52	1.3941 (15)	C56—H56	0.9500
C51—C56	1.3963 (15)	C64—C63	1.382 (2)
C51—C5	1.5308 (14)	C64—C65	1.382 (2)
C22—C23	1.3960 (15)	C64—H64	0.9500
C5—H5	1.0000	C55—C54	1.3866 (18)
C31—C32	1.3879 (15)	C55—H55	0.9500
C31—C36	1.3960 (15)	C63—H63	0.9500
C26—C25	1.3944 (15)	C54—H54	0.9500
C26—H26	0.9500	C35—H35	0.9500
C36—C35	1.3931 (15)	C67—H67A	0.9800
C36—H36	0.9500	C67—H67B	0.9800
C62—C63	1.3917 (17)	C67—H67C	0.9800
C62—C61	1.4119 (16)	C65—H65	0.9500
C52—C53	1.3926 (16)
O1—N2—N1	114.42 (8)	C26—C25—H25	120.6
N2—N1—C6	119.49 (8)	C31—C32—C33	120.95 (11)
N2—N1—C2	116.73 (8)	C31—C32—H32	119.5
C6—N1—C2	122.32 (8)	C33—C32—H32	119.5
C62—O4—C67	117.89 (10)	C25—C24—C23	120.99 (10)
C22—O3—C27	117.64 (9)	C25—C24—H24	119.5
C31—C3—C4	112.21 (8)	C23—C24—H24	119.5
C31—C3—C2	109.96 (8)	C54—C53—C52	120.51 (11)
C4—C3—C2	112.73 (8)	C54—C53—H53	119.7
C31—C3—H3	107.2	C52—C53—H53	119.7
C4—C3—H3	107.2	C24—C23—C22	119.98 (11)
C2—C3—H3	107.2	C24—C23—H23	120.0
O2—C4—C5	121.74 (9)	C22—C23—H23	120.0
O2—C4—C3	120.72 (10)	C66—C61—C62	119.13 (10)
C5—C4—C3	117.53 (8)	C66—C61—C6	123.72 (10)
N1—C2—C21	112.95 (8)	C62—C61—C6	117.14 (10)
N1—C2—C3	109.51 (8)	C34—C33—C32	119.89 (11)
C21—C2—C3	113.26 (8)	C34—C33—H33	120.1
N1—C2—H2	106.9	C32—C33—H33	120.1
C21—C2—H2	106.9	C61—C66—C65	120.56 (12)
C3—C2—H2	106.9	C61—C66—H66	119.7
N1—C6—C61	111.68 (8)	C65—C66—H66	119.7
N1—C6—C5	111.38 (8)	C33—C34—C35	119.68 (11)
C61—C6—C5	111.20 (8)	C33—C34—H34	120.2
N1—C6—H6	107.4	C35—C34—H34	120.2
C61—C6—H6	107.4	O3—C27—H27A	109.5
C5—C6—H6	107.4	O3—C27—H27B	109.5
C26—C21—C22	118.43 (9)	H27A—C27—H27B	109.5
C26—C21—C2	118.14 (9)	O3—C27—H27C	109.5
C22—C21—C2	123.32 (9)	H27A—C27—H27C	109.5
C52—C51—C56	118.54 (10)	H27B—C27—H27C	109.5
C52—C51—C5	124.56 (9)	C55—C56—C51	120.80 (11)
C56—C51—C5	116.88 (9)	C55—C56—H56	119.6
O3—C22—C23	123.27 (10)	C51—C56—H56	119.6
O3—C22—C21	116.63 (9)	C63—C64—C65	121.10 (12)
C23—C22—C21	120.10 (10)	C63—C64—H64	119.5
C4—C5—C51	108.85 (8)	C65—C64—H64	119.4
C4—C5—C6	111.56 (8)	C56—C55—C54	120.34 (11)
C51—C5—C6	115.77 (8)	C56—C55—H55	119.8
C4—C5—H5	106.7	C54—C55—H55	119.8
C51—C5—H5	106.7	C64—C63—C62	119.58 (13)
C6—C5—H5	106.7	C64—C63—H63	120.2
C32—C31—C36	118.84 (10)	C62—C63—H63	120.2
C32—C31—C3	120.18 (9)	C53—C54—C55	119.44 (11)
C36—C31—C3	120.93 (9)	C53—C54—H54	120.3
C25—C26—C21	121.60 (10)	C55—C54—H54	120.3
C25—C26—H26	119.2	C34—C35—C36	120.40 (11)
C21—C26—H26	119.2	C34—C35—H35	119.8
C35—C36—C31	120.23 (10)	C36—C35—H35	119.8
C35—C36—H36	119.9	O4—C67—H67A	109.5
C31—C36—H36	119.9	O4—C67—H67B	109.5
O4—C62—C63	124.92 (11)	H67A—C67—H67B	109.5
O4—C62—C61	114.92 (10)	O4—C67—H67C	109.5
C63—C62—C61	120.13 (12)	H67A—C67—H67C	109.5
C53—C52—C51	120.36 (10)	H67B—C67—H67C	109.5
C53—C52—H52	119.8	C64—C65—C66	119.49 (13)
C51—C52—H52	119.8	C64—C65—H65	120.3
C24—C25—C26	118.88 (11)	C66—C65—H65	120.3
C24—C25—H25	120.6
O1—N2—N1—C6	5.17 (13)	C4—C3—C31—C36	61.53 (12)
O1—N2—N1—C2	171.70 (8)	C2—C3—C31—C36	−64.80 (12)
C31—C3—C4—O2	48.25 (13)	C22—C21—C26—C25	0.10 (15)
C2—C3—C4—O2	173.07 (9)	C2—C21—C26—C25	−176.19 (9)
C31—C3—C4—C5	−132.27 (9)	C32—C31—C36—C35	−0.63 (16)
C2—C3—C4—C5	−7.45 (12)	C3—C31—C36—C35	176.63 (10)
N2—N1—C2—C21	23.96 (12)	C67—O4—C62—C63	−4.11 (17)
C6—N1—C2—C21	−169.92 (9)	C67—O4—C62—C61	177.72 (10)
N2—N1—C2—C3	151.19 (8)	C56—C51—C52—C53	−0.31 (16)
C6—N1—C2—C3	−42.70 (12)	C5—C51—C52—C53	−179.09 (10)
C31—C3—C2—N1	173.68 (8)	C21—C26—C25—C24	0.76 (16)
C4—C3—C2—N1	47.65 (11)	C36—C31—C32—C33	0.64 (16)
C31—C3—C2—C21	−59.26 (11)	C3—C31—C32—C33	−176.64 (10)
C4—C3—C2—C21	174.70 (8)	C26—C25—C24—C23	−0.91 (17)
N2—N1—C6—C61	−74.89 (11)	C51—C52—C53—C54	1.14 (17)
C2—N1—C6—C61	119.37 (10)	C25—C24—C23—C22	0.20 (17)
N2—N1—C6—C5	160.12 (9)	O3—C22—C23—C24	−179.49 (10)
C2—N1—C6—C5	−5.63 (13)	C21—C22—C23—C24	0.67 (16)
N1—C2—C21—C26	−114.75 (10)	O4—C62—C61—C66	178.76 (10)
C3—C2—C21—C26	120.03 (10)	C63—C62—C61—C66	0.49 (16)
N1—C2—C21—C22	69.16 (12)	O4—C62—C61—C6	−0.60 (14)
C3—C2—C21—C22	−56.07 (13)	C63—C62—C61—C6	−178.87 (10)
C27—O3—C22—C23	1.41 (15)	N1—C6—C61—C66	−19.75 (14)
C27—O3—C22—C21	−178.75 (9)	C5—C6—C61—C66	105.35 (12)
C26—C21—C22—O3	179.34 (9)	N1—C6—C61—C62	159.58 (9)
C2—C21—C22—O3	−4.58 (15)	C5—C6—C61—C62	−75.33 (12)
C26—C21—C22—C23	−0.81 (15)	C31—C32—C33—C34	0.11 (18)
C2—C21—C22—C23	175.27 (10)	C62—C61—C66—C65	−0.47 (17)
O2—C4—C5—C51	−92.75 (12)	C6—C61—C66—C65	178.85 (11)
C3—C4—C5—C51	87.78 (10)	C32—C33—C34—C35	−0.88 (18)
O2—C4—C5—C6	138.28 (10)	C52—C51—C56—C55	−0.74 (18)
C3—C4—C5—C6	−41.19 (12)	C5—C51—C56—C55	178.14 (11)
C52—C51—C5—C4	−111.39 (11)	C51—C56—C55—C54	1.0 (2)
C56—C51—C5—C4	69.81 (12)	C65—C64—C63—C62	−0.4 (2)
C52—C51—C5—C6	15.20 (14)	O4—C62—C63—C64	−178.17 (11)
C56—C51—C5—C6	−163.61 (10)	C61—C62—C63—C64	−0.09 (18)
N1—C6—C5—C4	47.57 (11)	C52—C53—C54—C55	−0.91 (18)
C61—C6—C5—C4	−77.69 (11)	C56—C55—C54—C53	−0.1 (2)
N1—C6—C5—C51	−77.64 (11)	C33—C34—C35—C36	0.89 (18)
C61—C6—C5—C51	157.10 (9)	C31—C36—C35—C34	−0.13 (17)
C4—C3—C31—C32	−121.25 (10)	C63—C64—C65—C66	0.4 (2)
C2—C3—C31—C32	112.43 (10)	C61—C66—C65—C64	0.04 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C66—H66···O3	0.95	2.47	3.4138 (16)	176
C23—H23···O1^i	0.95	2.59	3.4370 (14)	149
C23—H23···N2^i	0.95	2.55	3.3796 (14)	146

Symmetry code: (i) −x, −y+1, −z.