3-(3-Hydroxy­anilino)-1,3-diphenyl­prop-2-en-1-one

The asymmetric unit of the title compound, C₂₁H₁₇NO₂, contains two discrete mol­ecules with similar geometric parameters. Intra­molecular N—H...O=C hydrogen bonding stabilizes each of the two mol­ecules. Intermolecular O—H...O=C hydrogen bonds form two [100] chains having R₂²(16) rings. Inter­molecular C—H...O—H and C—H...O=C hydrogen bonds lead to the formation of R₂²(7) and R₂¹(6) rings.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.086
• wR factor = 0.163
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

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Computing details

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

3-(3-Hydroxyanilino)-1,3-diphenylprop-2-en-1-one

Crystal data

C21H17NO2	F(000) = 2656
Mr = 315.36	Dx = 1.275 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 17861 reflections
a = 7.1855 (5) Å	θ = 3.0–25.3°
b = 24.4898 (19) Å	µ = 0.08 mm^−1
c = 37.352 (3) Å	T = 193 K
V = 6572.9 (9) Å^3	Block, yellow
Z = 16	0.50 × 0.30 × 0.24 mm

Data collection

Rigaku Mercury diffractometer	6016 independent reflections
Radiation source: fine-focus sealed tube	5034 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
Detector resolution: 7.31 pixels mm^-1	θmax = 25.4°, θmin = 3.0°
ω scans	h = −7→8
Absorption correction: multi-scan (Jacobson, 1998)	k = −28→29
Tmin = 0.963, Tmax = 0.980	l = −45→45
57180 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.163	H-atom parameters constrained
S = 1.30	w = 1/[σ^2(Fo^2) + (0.038P)^2 + 4.4272P] where P = (Fo^2 + 2Fc^2)/3
6016 reflections	(Δ/σ)max < 0.001
436 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

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
C1	0.7503 (4)	0.51682 (15)	0.52162 (8)	0.0481 (8)
H1	0.7844	0.4799	0.5258	0.058*
C2	0.7075 (5)	0.5506 (2)	0.55015 (10)	0.0683 (12)
H2	0.7150	0.5370	0.5739	0.082*
C3	0.6540 (5)	0.6037 (2)	0.54424 (13)	0.0790 (15)
H3	0.6250	0.6268	0.5639	0.095*
C4	0.6426 (5)	0.62337 (16)	0.51015 (14)	0.0732 (13)
H4	0.6026	0.6599	0.5062	0.088*
C5	0.6885 (5)	0.59083 (13)	0.48137 (10)	0.0528 (9)
H5	0.6827	0.6051	0.4578	0.063*
C6	0.7434 (4)	0.53694 (12)	0.48696 (8)	0.0386 (7)
C7	0.8005 (4)	0.50332 (12)	0.45579 (8)	0.0344 (7)
C8	0.7804 (4)	0.44593 (12)	0.45708 (8)	0.0371 (7)
H8	0.7258	0.4306	0.4780	0.045*
C9	0.8340 (4)	0.41056 (11)	0.43031 (8)	0.0361 (7)
C10	0.7962 (4)	0.35138 (12)	0.43519 (8)	0.0382 (7)
C11	0.7011 (4)	0.32217 (12)	0.40913 (9)	0.0442 (8)
H11	0.6717	0.3390	0.3869	0.053*
C12	0.6487 (5)	0.26849 (13)	0.41546 (10)	0.0526 (9)
H12	0.5837	0.2486	0.3975	0.063*
C13	0.6906 (6)	0.24391 (14)	0.44756 (11)	0.0627 (10)
H13	0.6538	0.2072	0.4518	0.075*
C14	0.7861 (6)	0.27250 (14)	0.47355 (11)	0.0636 (11)
H14	0.8162	0.2553	0.4956	0.076*
C15	0.8382 (5)	0.32632 (13)	0.46760 (9)	0.0500 (8)
H15	0.9026	0.3460	0.4857	0.060*
C16	1.0048 (4)	0.40224 (11)	0.37184 (8)	0.0380 (7)
C17	1.0016 (4)	0.42572 (11)	0.33798 (8)	0.0396 (7)
H17	0.9292	0.4575	0.3336	0.048*
C18	1.1045 (5)	0.40248 (12)	0.31077 (8)	0.0407 (7)
C19	1.2095 (4)	0.35627 (12)	0.31663 (9)	0.0442 (8)
H19	1.2783	0.3402	0.2976	0.053*
C20	1.2134 (4)	0.33362 (12)	0.35056 (9)	0.0451 (8)
H20	1.2874	0.3021	0.3548	0.054*
C21	1.1117 (4)	0.35590 (12)	0.37844 (9)	0.0428 (8)
H21	1.1147	0.3399	0.4016	0.051*
C22	0.0536 (5)	0.58036 (13)	0.18085 (8)	0.0454 (8)
H22	0.0706	0.6180	0.1861	0.055*
C23	0.0664 (5)	0.56271 (14)	0.14571 (9)	0.0512 (9)
H23	0.0930	0.5880	0.1271	0.061*
C24	0.0406 (5)	0.50838 (14)	0.13777 (9)	0.0493 (8)
H24	0.0481	0.4961	0.1137	0.059*
C25	0.0038 (5)	0.47208 (14)	0.16481 (9)	0.0571 (10)
H25	−0.0139	0.4346	0.1593	0.069*
C26	−0.0079 (5)	0.48954 (13)	0.20000 (9)	0.0511 (9)
H26	−0.0328	0.4639	0.2185	0.061*
C27	0.0168 (4)	0.54442 (12)	0.20840 (8)	0.0353 (7)
C28	0.0061 (4)	0.56347 (11)	0.24623 (8)	0.0350 (7)
C29	−0.0370 (4)	0.61948 (11)	0.25305 (8)	0.0341 (7)
H29	−0.0827	0.6407	0.2337	0.041*
C30	−0.0171 (4)	0.64470 (11)	0.28559 (8)	0.0339 (7)
C31	−0.0707 (4)	0.70329 (11)	0.28944 (7)	0.0336 (7)
C32	−0.1864 (4)	0.71961 (12)	0.31745 (8)	0.0391 (7)
H32	−0.2231	0.6940	0.3352	0.047*
C33	−0.2479 (4)	0.77317 (13)	0.31928 (8)	0.0452 (8)
H33	−0.3290	0.7839	0.3381	0.054*
C34	−0.1923 (4)	0.81101 (13)	0.29406 (9)	0.0450 (8)
H34	−0.2334	0.8478	0.2957	0.054*
C35	−0.0768 (4)	0.79498 (12)	0.26650 (8)	0.0408 (7)
H35	−0.0377	0.8209	0.2491	0.049*
C36	−0.0174 (4)	0.74128 (11)	0.26398 (8)	0.0368 (7)
H36	0.0604	0.7305	0.2447	0.044*
C37	0.1219 (4)	0.63920 (11)	0.34689 (8)	0.0362 (7)
C38	0.0723 (4)	0.61492 (11)	0.37911 (8)	0.0374 (7)
H38	−0.0166	0.5862	0.3794	0.045*
C39	0.1522 (4)	0.63252 (12)	0.41056 (8)	0.0402 (7)
C40	0.2825 (5)	0.67414 (12)	0.41048 (8)	0.0436 (8)
H40	0.3382	0.6862	0.4322	0.052*
C41	0.3300 (5)	0.69794 (12)	0.37792 (9)	0.0460 (8)
H41	0.4204	0.7262	0.3775	0.055*
C42	0.2490 (4)	0.68149 (12)	0.34622 (8)	0.0416 (7)
H42	0.2802	0.6989	0.3243	0.050*
N1	0.9050 (4)	0.42973 (9)	0.39945 (6)	0.0382 (6)
H1N	0.8870	0.4648	0.3957	0.046*
N2	0.0412 (4)	0.61747 (10)	0.31505 (6)	0.0403 (6)
H2N	0.0275	0.5818	0.3145	0.048*
O1	0.8664 (3)	0.52780 (8)	0.42869 (5)	0.0422 (5)
O2	1.1048 (4)	0.42244 (9)	0.27639 (6)	0.0542 (6)
H2O	1.0748	0.4556	0.2766	0.081*
O3	0.0357 (3)	0.53051 (8)	0.27144 (5)	0.0459 (6)
O4	0.1035 (4)	0.61085 (9)	0.44302 (5)	0.0520 (6)
H4O	0.0279	0.5851	0.4399	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0323 (17)	0.071 (2)	0.0407 (19)	−0.0032 (16)	0.0013 (14)	−0.0130 (17)
C2	0.039 (2)	0.120 (4)	0.046 (2)	−0.008 (2)	0.0044 (16)	−0.028 (2)
C3	0.042 (2)	0.107 (4)	0.088 (3)	−0.013 (2)	0.019 (2)	−0.062 (3)
C4	0.056 (3)	0.054 (2)	0.110 (4)	−0.0077 (19)	0.021 (2)	−0.034 (3)
C5	0.049 (2)	0.0399 (18)	0.070 (2)	−0.0060 (16)	0.0117 (18)	−0.0112 (17)
C6	0.0318 (16)	0.0427 (17)	0.0412 (18)	−0.0041 (14)	0.0007 (13)	−0.0088 (14)
C7	0.0291 (16)	0.0402 (16)	0.0339 (16)	−0.0004 (13)	−0.0027 (12)	−0.0003 (13)
C8	0.0391 (17)	0.0356 (15)	0.0368 (17)	−0.0068 (14)	0.0054 (13)	0.0006 (13)
C9	0.0368 (17)	0.0352 (15)	0.0365 (17)	−0.0032 (13)	0.0003 (13)	−0.0019 (13)
C10	0.0359 (17)	0.0343 (15)	0.0443 (18)	−0.0029 (13)	0.0041 (14)	−0.0044 (14)
C11	0.0458 (19)	0.0410 (17)	0.0459 (19)	−0.0029 (15)	0.0039 (15)	−0.0046 (15)
C12	0.059 (2)	0.0421 (18)	0.057 (2)	−0.0102 (17)	0.0028 (18)	−0.0089 (17)
C13	0.076 (3)	0.0361 (18)	0.076 (3)	−0.0102 (18)	0.006 (2)	−0.0011 (19)
C14	0.084 (3)	0.0413 (19)	0.065 (2)	−0.004 (2)	−0.008 (2)	0.0090 (18)
C15	0.057 (2)	0.0413 (18)	0.052 (2)	−0.0045 (16)	−0.0058 (17)	−0.0016 (16)
C16	0.0378 (17)	0.0335 (15)	0.0428 (18)	−0.0015 (13)	−0.0005 (14)	−0.0054 (13)
C17	0.0445 (18)	0.0294 (15)	0.0449 (18)	0.0010 (14)	0.0028 (14)	−0.0033 (14)
C18	0.0474 (19)	0.0329 (16)	0.0419 (18)	−0.0010 (14)	0.0025 (15)	−0.0047 (14)
C19	0.0444 (19)	0.0388 (17)	0.049 (2)	0.0028 (15)	0.0051 (15)	−0.0100 (15)
C20	0.0438 (19)	0.0343 (16)	0.057 (2)	0.0055 (14)	−0.0006 (16)	−0.0055 (15)
C21	0.0427 (18)	0.0402 (17)	0.0455 (19)	−0.0004 (15)	−0.0010 (15)	−0.0012 (15)
C22	0.053 (2)	0.0429 (18)	0.0404 (18)	−0.0029 (15)	0.0024 (16)	−0.0040 (15)
C23	0.060 (2)	0.055 (2)	0.0382 (18)	−0.0045 (18)	0.0067 (16)	0.0013 (16)
C24	0.046 (2)	0.063 (2)	0.0390 (18)	−0.0050 (17)	0.0046 (15)	−0.0136 (17)
C25	0.073 (3)	0.050 (2)	0.049 (2)	−0.0112 (19)	0.0083 (18)	−0.0156 (17)
C26	0.068 (2)	0.0425 (18)	0.0432 (19)	−0.0093 (17)	0.0033 (17)	−0.0049 (15)
C27	0.0327 (16)	0.0379 (16)	0.0353 (16)	−0.0007 (13)	0.0009 (13)	−0.0035 (13)
C28	0.0315 (16)	0.0394 (15)	0.0342 (16)	−0.0033 (13)	0.0003 (12)	−0.0003 (14)
C29	0.0355 (16)	0.0369 (15)	0.0299 (15)	0.0013 (13)	−0.0005 (12)	0.0014 (13)
C30	0.0303 (15)	0.0366 (16)	0.0347 (16)	−0.0024 (13)	0.0039 (12)	0.0023 (13)
C31	0.0339 (16)	0.0352 (16)	0.0317 (16)	−0.0019 (13)	−0.0014 (13)	−0.0032 (13)
C32	0.0427 (18)	0.0442 (17)	0.0303 (16)	−0.0013 (14)	0.0039 (13)	−0.0043 (13)
C33	0.0390 (18)	0.0516 (19)	0.0449 (19)	0.0036 (15)	−0.0012 (15)	−0.0167 (16)
C34	0.0422 (18)	0.0374 (17)	0.055 (2)	0.0024 (15)	−0.0084 (16)	−0.0117 (16)
C35	0.0425 (18)	0.0337 (16)	0.0461 (18)	−0.0026 (14)	−0.0074 (15)	0.0026 (14)
C36	0.0353 (16)	0.0403 (16)	0.0347 (16)	0.0003 (13)	0.0018 (13)	−0.0010 (13)
C37	0.0415 (17)	0.0344 (15)	0.0326 (16)	0.0021 (13)	0.0009 (13)	−0.0010 (13)
C38	0.0438 (18)	0.0310 (15)	0.0374 (17)	−0.0043 (14)	−0.0035 (14)	0.0000 (13)
C39	0.0472 (19)	0.0355 (16)	0.0378 (18)	−0.0024 (14)	−0.0017 (14)	0.0012 (14)
C40	0.0488 (19)	0.0383 (17)	0.0436 (18)	−0.0042 (15)	−0.0113 (15)	0.0012 (15)
C41	0.0449 (19)	0.0378 (17)	0.055 (2)	−0.0076 (15)	−0.0029 (16)	0.0022 (15)
C42	0.0485 (19)	0.0379 (16)	0.0384 (17)	−0.0059 (15)	−0.0020 (15)	0.0059 (14)
N1	0.0472 (15)	0.0305 (12)	0.0367 (14)	0.0015 (11)	0.0032 (12)	−0.0024 (11)
N2	0.0573 (17)	0.0315 (13)	0.0323 (14)	−0.0057 (12)	−0.0027 (12)	0.0021 (11)
O1	0.0556 (14)	0.0356 (11)	0.0354 (12)	−0.0031 (10)	0.0023 (10)	0.0006 (9)
O2	0.0769 (17)	0.0432 (13)	0.0425 (13)	0.0081 (13)	0.0106 (12)	−0.0014 (10)
O3	0.0622 (15)	0.0378 (11)	0.0377 (12)	0.0012 (11)	−0.0018 (11)	0.0015 (10)
O4	0.0709 (17)	0.0503 (14)	0.0348 (12)	−0.0181 (12)	−0.0039 (11)	0.0057 (10)

Geometric parameters (Å, º)

C1—C2	1.383 (5)	C22—H22	0.9500
C1—C6	1.386 (4)	C23—C24	1.376 (4)
C1—H1	0.9500	C23—H23	0.9500
C2—C3	1.375 (6)	C24—C25	1.371 (5)
C2—H2	0.9500	C24—H24	0.9500
C3—C4	1.364 (6)	C25—C26	1.384 (4)
C3—H3	0.9500	C25—H25	0.9500
C4—C5	1.378 (5)	C26—C27	1.392 (4)
C4—H4	0.9500	C26—H26	0.9500
C5—C6	1.393 (4)	C27—C28	1.490 (4)
C5—H5	0.9500	C28—O3	1.258 (3)
C6—C7	1.484 (4)	C28—C29	1.429 (4)
C7—O1	1.268 (3)	C29—C30	1.371 (4)
C7—C8	1.414 (4)	C29—H29	0.9500
C8—C9	1.378 (4)	C30—N2	1.353 (4)
C8—H8	0.9500	C30—C31	1.492 (4)
C9—N1	1.345 (4)	C31—C36	1.384 (4)
C9—C10	1.486 (4)	C31—C32	1.395 (4)
C10—C11	1.388 (4)	C32—C33	1.386 (4)
C10—C15	1.390 (4)	C32—H32	0.9500
C11—C12	1.388 (4)	C33—C34	1.380 (4)
C11—H11	0.9500	C33—H33	0.9500
C12—C13	1.375 (5)	C34—C35	1.380 (4)
C12—H12	0.9500	C34—H34	0.9500
C13—C14	1.380 (5)	C35—C36	1.386 (4)
C13—H13	0.9500	C35—H35	0.9500
C14—C15	1.388 (4)	C36—H36	0.9500
C14—H14	0.9500	C37—C42	1.381 (4)
C15—H15	0.9500	C37—C38	1.389 (4)
C16—C17	1.389 (4)	C37—N2	1.426 (4)
C16—C21	1.392 (4)	C38—C39	1.377 (4)
C16—N1	1.425 (4)	C38—H38	0.9500
C17—C18	1.379 (4)	C39—O4	1.369 (3)
C17—H17	0.9500	C39—C40	1.384 (4)
C18—O2	1.374 (4)	C40—C41	1.391 (4)
C18—C19	1.378 (4)	C40—H40	0.9500
C19—C20	1.384 (4)	C41—C42	1.380 (4)
C19—H19	0.9500	C41—H41	0.9500
C20—C21	1.385 (4)	C42—H42	0.9500
C20—H20	0.9500	N1—H1N	0.8800
C21—H21	0.9500	N2—H2N	0.8800
C22—C27	1.380 (4)	O2—H2O	0.8400
C22—C23	1.385 (4)	O4—H4O	0.8400
C2—C1—C6	119.9 (4)	C24—C23—H23	120.1
C2—C1—H1	120.0	C22—C23—H23	120.1
C6—C1—H1	120.0	C25—C24—C23	119.6 (3)
C3—C2—C1	120.3 (4)	C25—C24—H24	120.2
C3—C2—H2	119.9	C23—C24—H24	120.2
C1—C2—H2	119.9	C24—C25—C26	120.7 (3)
C4—C3—C2	120.1 (4)	C24—C25—H25	119.6
C4—C3—H3	120.0	C26—C25—H25	119.6
C2—C3—H3	120.0	C25—C26—C27	120.3 (3)
C3—C4—C5	120.6 (4)	C25—C26—H26	119.8
C3—C4—H4	119.7	C27—C26—H26	119.8
C5—C4—H4	119.7	C22—C27—C26	118.2 (3)
C4—C5—C6	119.9 (4)	C22—C27—C28	121.2 (3)
C4—C5—H5	120.0	C26—C27—C28	120.6 (3)
C6—C5—H5	120.0	O3—C28—C29	121.3 (3)
C1—C6—C5	119.1 (3)	O3—C28—C27	120.0 (3)
C1—C6—C7	121.7 (3)	C29—C28—C27	118.7 (3)
C5—C6—C7	119.1 (3)	C30—C29—C28	124.6 (3)
O1—C7—C8	122.4 (3)	C30—C29—H29	117.7
O1—C7—C6	117.8 (3)	C28—C29—H29	117.7
C8—C7—C6	119.8 (3)	N2—C30—C29	122.1 (3)
C9—C8—C7	124.9 (3)	N2—C30—C31	118.4 (2)
C9—C8—H8	117.6	C29—C30—C31	119.4 (3)
C7—C8—H8	117.6	C36—C31—C32	119.2 (3)
N1—C9—C8	120.6 (3)	C36—C31—C30	120.6 (3)
N1—C9—C10	121.0 (3)	C32—C31—C30	120.1 (3)
C8—C9—C10	118.2 (3)	C33—C32—C31	119.9 (3)
C11—C10—C15	119.3 (3)	C33—C32—H32	120.1
C11—C10—C9	120.4 (3)	C31—C32—H32	120.1
C15—C10—C9	119.9 (3)	C34—C33—C32	120.6 (3)
C12—C11—C10	120.1 (3)	C34—C33—H33	119.7
C12—C11—H11	119.9	C32—C33—H33	119.7
C10—C11—H11	119.9	C35—C34—C33	119.5 (3)
C13—C12—C11	120.3 (3)	C35—C34—H34	120.3
C13—C12—H12	119.9	C33—C34—H34	120.3
C11—C12—H12	119.9	C34—C35—C36	120.4 (3)
C12—C13—C14	120.0 (3)	C34—C35—H35	119.8
C12—C13—H13	120.0	C36—C35—H35	119.8
C14—C13—H13	120.0	C31—C36—C35	120.4 (3)
C13—C14—C15	120.2 (3)	C31—C36—H36	119.8
C13—C14—H14	119.9	C35—C36—H36	119.8
C15—C14—H14	119.9	C42—C37—C38	120.4 (3)
C14—C15—C10	120.0 (3)	C42—C37—N2	122.3 (3)
C14—C15—H15	120.0	C38—C37—N2	117.3 (3)
C10—C15—H15	120.0	C39—C38—C37	119.9 (3)
C17—C16—C21	120.5 (3)	C39—C38—H38	120.1
C17—C16—N1	117.0 (3)	C37—C38—H38	120.1
C21—C16—N1	122.3 (3)	O4—C39—C38	121.8 (3)
C18—C17—C16	119.4 (3)	O4—C39—C40	117.4 (3)
C18—C17—H17	120.3	C38—C39—C40	120.7 (3)
C16—C17—H17	120.3	C39—C40—C41	118.5 (3)
O2—C18—C19	116.1 (3)	C39—C40—H40	120.8
O2—C18—C17	122.9 (3)	C41—C40—H40	120.8
C19—C18—C17	121.0 (3)	C42—C41—C40	121.6 (3)
C18—C19—C20	119.1 (3)	C42—C41—H41	119.2
C18—C19—H19	120.5	C40—C41—H41	119.2
C20—C19—H19	120.5	C41—C42—C37	118.8 (3)
C19—C20—C21	121.4 (3)	C41—C42—H42	120.6
C19—C20—H20	119.3	C37—C42—H42	120.6
C21—C20—H20	119.3	C9—N1—C16	130.2 (2)
C20—C21—C16	118.6 (3)	C9—N1—H1N	114.9
C20—C21—H21	120.7	C16—N1—H1N	114.9
C16—C21—H21	120.7	C30—N2—C37	128.3 (2)
C27—C22—C23	121.4 (3)	C30—N2—H2N	115.8
C27—C22—H22	119.3	C37—N2—H2N	115.8
C23—C22—H22	119.3	C18—O2—H2O	109.5
C24—C23—C22	119.8 (3)	C39—O4—H4O	109.5
C6—C1—C2—C3	1.4 (5)	C23—C22—C27—C26	−0.1 (5)
C1—C2—C3—C4	0.1 (6)	C23—C22—C27—C28	179.0 (3)
C2—C3—C4—C5	−1.6 (6)	C25—C26—C27—C22	−0.3 (5)
C3—C4—C5—C6	1.4 (6)	C25—C26—C27—C28	−179.5 (3)
C2—C1—C6—C5	−1.6 (5)	C22—C27—C28—O3	−155.8 (3)
C2—C1—C6—C7	175.8 (3)	C26—C27—C28—O3	23.3 (4)
C4—C5—C6—C1	0.2 (5)	C22—C27—C28—C29	23.8 (4)
C4—C5—C6—C7	−177.2 (3)	C26—C27—C28—C29	−157.0 (3)
C1—C6—C7—O1	−150.5 (3)	O3—C28—C29—C30	12.6 (5)
C5—C6—C7—O1	26.9 (4)	C27—C28—C29—C30	−167.1 (3)
C1—C6—C7—C8	29.5 (4)	C28—C29—C30—N2	−2.2 (5)
C5—C6—C7—C8	−153.1 (3)	C28—C29—C30—C31	−178.8 (3)
O1—C7—C8—C9	2.2 (5)	N2—C30—C31—C36	137.9 (3)
C6—C7—C8—C9	−177.8 (3)	C29—C30—C31—C36	−45.3 (4)
C7—C8—C9—N1	−2.8 (5)	N2—C30—C31—C32	−46.7 (4)
C7—C8—C9—C10	−177.6 (3)	C29—C30—C31—C32	130.1 (3)
N1—C9—C10—C11	−47.9 (4)	C36—C31—C32—C33	0.6 (4)
C8—C9—C10—C11	126.8 (3)	C30—C31—C32—C33	−174.8 (3)
N1—C9—C10—C15	139.0 (3)	C31—C32—C33—C34	−1.5 (5)
C8—C9—C10—C15	−46.2 (4)	C32—C33—C34—C35	1.0 (5)
C15—C10—C11—C12	0.0 (5)	C33—C34—C35—C36	0.3 (5)
C9—C10—C11—C12	−173.1 (3)	C32—C31—C36—C35	0.6 (4)
C10—C11—C12—C13	0.0 (5)	C30—C31—C36—C35	176.1 (3)
C11—C12—C13—C14	−0.4 (6)	C34—C35—C36—C31	−1.1 (5)
C12—C13—C14—C15	0.8 (6)	C42—C37—C38—C39	−0.9 (5)
C13—C14—C15—C10	−0.8 (6)	N2—C37—C38—C39	177.1 (3)
C11—C10—C15—C14	0.4 (5)	C37—C38—C39—O4	178.1 (3)
C9—C10—C15—C14	173.5 (3)	C37—C38—C39—C40	−0.3 (5)
C21—C16—C17—C18	0.4 (5)	O4—C39—C40—C41	−178.0 (3)
N1—C16—C17—C18	176.4 (3)	C38—C39—C40—C41	0.3 (5)
C16—C17—C18—O2	178.3 (3)	C39—C40—C41—C42	0.8 (5)
C16—C17—C18—C19	0.3 (5)	C40—C41—C42—C37	−2.0 (5)
O2—C18—C19—C20	−179.2 (3)	C38—C37—C42—C41	2.0 (5)
C17—C18—C19—C20	−1.0 (5)	N2—C37—C42—C41	−175.9 (3)
C18—C19—C20—C21	1.1 (5)	C8—C9—N1—C16	164.8 (3)
C19—C20—C21—C16	−0.4 (5)	C10—C9—N1—C16	−20.5 (5)
C17—C16—C21—C20	−0.4 (5)	C17—C16—N1—C9	156.7 (3)
N1—C16—C21—C20	−176.1 (3)	C21—C16—N1—C9	−27.5 (5)
C27—C22—C23—C24	0.5 (5)	C29—C30—N2—C37	159.0 (3)
C22—C23—C24—C25	−0.5 (5)	C31—C30—N2—C37	−24.4 (4)
C23—C24—C25—C26	0.1 (6)	C42—C37—N2—C30	−39.7 (5)
C24—C25—C26—C27	0.3 (6)	C38—C37—N2—C30	142.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3^i	0.84	1.87	2.699 (3)	171
O4—H4O···O1^ii	0.84	1.87	2.706 (3)	175
N1—H1N···O1	0.88	1.98	2.653 (3)	132
N2—H2N···O3	0.88	2.04	2.681 (3)	129
C38—H38···O1^ii	0.95	2.48	3.189 (4)	132
C26—H26···O2^ii	0.95	2.59	3.391 (4)	143
C36—H36···Cg5^iii	0.95	2.68	3.488 (3)	144

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