Structure determination from powder data without prior indexing, using a similarity measure based on cross-correlation functions

A method to refine organic crystal structures from powder diffraction data with incorrect lattice parameters has been developed. The method is based on the similarity measure developed by de Gelder et al. [J. Comput. Chem. (2001), 22, 273–289], using the cross- and auto-correlation functions of a simulated and an experimental powder pattern. The lattice parameters, molecular position, molecular orientation and selected intramolecular degrees of freedom are optimized until the similarity measure reaches a maximum; subsequently, a Rietveld refinement is carried out. The program FIDEL (FIt with DEviating Lattice parameters) implements this method. The procedure is also suitable for unindexed powder data, powder diagrams of very low quality and powder diagrams of non-phase-pure samples. Various applications are shown, including structure determinations from powder data using crystal structure predictions by standard force-field methods. Other useful applications include the automatic structure determination from powder data starting from the crystal structures of isostructural compounds (e.g. a solvate, hydrate or chemical derivative), or from crystal data measured at a different temperature or pressure.

S1. Experimental

S1.1. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

S2. Results and discussion

Computing details

For both compounds, data collection: STOE WinXPOW (STOE & Cie GmbH, 2006); cell refinement: TOPAS Academic (Coelho, 2007); data reduction: TOPAS Academic (Coelho, 2007); program(s) used to solve structure: FIDEL (Habermehl et al., 2014); program(s) used to refine structure: TOPAS Academic (Coelho, 2007).

Figures

(I) 4-(p-Chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-1-piperidinebutyramide hydrochloride

Crystal data

C29H34ClN2O2^+·Cl^−	Z = 4
Mr = 513.48	F(000) = 1088.0
Monoclinic, P21/c	Dx = 1.274 Mg m^−3
a = 16.7095 (8) Å	Cu Kα1 radiation, λ = 1.54056 Å
b = 12.3773 (5) Å	µ = 2.40 mm^−1
c = 13.2135 (5) Å	T = 298 K
β = 101.642 (3)°	colourless
V = 2676.59 (19) Å^3	cylinder, 10 × 1 mm

Data collection

STOE Stadi-P diffractometer	Data collection mode: transmission
Radiation source: sealed x-ray tube	Scan method: step
Primary focussing Ge 111 monochromator	2θmin = 2.000°, 2θmax = 100.190°, 2θstep = 0.01°
Specimen mounting: glass capillary

Refinement

Least-squares matrix: full with fixed elements per cycle	259 parameters
Rp = 0.043	201 restraints
Rwp = 0.060	0 constraints
Rexp = 0.027	All H-atom parameters refined
RBragg = 0.030	Weighting scheme based on measured s.u.'s
χ^2 = 5.081	(Δ/σ)max = 0.001
9820 data points	Background function: Chebyshev with 20 terms
Profile function: modified Thompson-Cox-Hastings pseudo-Voigt	Preferred orientation correction: none

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.5327 (3)	0.0795 (3)	0.8847 (3)	0.05469
C2	0.3187 (2)	0.3966 (3)	0.4917 (3)	0.04888
C3	0.3407 (2)	0.2845 (3)	0.4562 (3)	0.04888
H4	0.3564 (9)	0.4541 (10)	0.4765 (10)	0.05866
H5	0.3207 (10)	0.3970 (11)	0.5672 (9)	0.05866
C6	0.2305 (3)	0.4170 (3)	0.4290 (3)	0.04888
N7	0.4281 (3)	0.2629 (3)	0.5012 (3)	0.04888
H8	0.3051 (10)	0.2283 (10)	0.4777 (10)	0.05866
H9	0.3307 (11)	0.2830 (10)	0.3791 (9)	0.05866
C10	0.1803 (4)	0.3035 (4)	0.4120 (3)	0.04888
C11	0.1911 (2)	0.5124 (3)	0.4731 (3)	0.04888
C12	0.2358 (3)	0.4579 (2)	0.3198 (3)	0.04888
H13	0.4584 (11)	0.3179 (10)	0.4753 (11)	0.05866
C14	0.4495 (2)	0.2614 (4)	0.6172 (3)	0.04888
C15	0.4593 (2)	0.1576 (3)	0.4666 (3)	0.04888
O16	0.1554 (6)	0.2672 (6)	0.3223 (5)	0.04888
N17	0.1434 (3)	0.2622 (5)	0.4894 (3)	0.04888
C18	0.1005 (2)	0.5257 (3)	0.4455 (3)	0.04888
C19	0.2454 (2)	0.5844 (3)	0.5392 (2)	0.04888
C20	0.1591 (3)	0.4829 (3)	0.2418 (3)	0.04888
C21	0.3143 (3)	0.4704 (3)	0.2965 (3)	0.04888
C22	0.5455 (3)	0.2665 (3)	0.6529 (3)	0.04888
H23	0.4276 (9)	0.1923 (10)	0.6411 (9)	0.05866
H24	0.4208 (10)	0.3228 (10)	0.6438 (9)	0.05866
H25	0.4434 (11)	0.1531 (11)	0.3916 (9)	0.05866
H26	0.4324 (9)	0.0964 (10)	0.4961 (10)	0.05866
C27	0.5545 (3)	0.1535 (4)	0.5040 (3)	0.04888
C28	0.1729 (3)	0.2951 (3)	0.5990 (3)	0.04888
C29	0.0652 (3)	0.1938 (3)	0.4606 (3)	0.04888
H30	0.0658 (9)	0.4753 (11)	0.4003 (10)	0.05866
C31	0.0626 (2)	0.6112 (3)	0.4839 (3)	0.04888
C32	0.2048 (2)	0.6679 (3)	0.5755 (3)	0.04888
H33	0.3063 (10)	0.5766 (11)	0.5580 (9)	0.05866
H34	0.1012 (9)	0.4767 (11)	0.2532 (9)	0.05866
C35	0.1692 (3)	0.5179 (2)	0.1486 (3)	0.04888
C36	0.3206 (2)	0.5043 (2)	0.2040 (3)	0.04888
H37	0.3644 (9)	0.4556 (10)	0.3453 (9)	0.05866
C38	0.5854 (3)	0.1586 (3)	0.6240 (3)	0.04888
H39	0.5602 (10)	0.2768 (10)	0.7286 (10)	0.05866
H40	0.5691 (10)	0.3300 (10)	0.6214 (9)	0.05866
H41	0.5749 (9)	0.0854 (11)	0.4792 (9)	0.05866
H42	0.5805 (9)	0.2143 (10)	0.4729 (10)	0.05866
H43	0.1879 (9)	0.2316 (10)	0.6424 (10)	0.05866
H44	0.2231 (10)	0.3397 (11)	0.6053 (10)	0.05866
H45	0.1276 (10)	0.3361 (11)	0.6207 (10)	0.05866
H46	0.0515 (12)	0.1831 (10)	0.3844 (11)	0.05866
H47	0.0159 (12)	0.2301 (10)	0.4805 (12)	0.05866
H48	0.0736 (10)	0.1218 (10)	0.4938 (11)	0.05866
H49	0.0032 (12)	0.6219 (10)	0.4675 (10)	0.05866
C50	0.1153 (2)	0.6821 (3)	0.5487 (3)	0.04888
H51	0.2383 (10)	0.7161 (10)	0.6189 (9)	0.05866
H52	0.1203 (9)	0.5341 (12)	0.0966 (9)	0.05866
C53	0.2511 (3)	0.5283 (2)	0.1300 (3)	0.04888
H54	0.3734 (9)	0.5102 (11)	0.1903 (9)	0.05866
O55	0.5512 (4)	0.0644 (4)	0.6587 (4)	0.04888
C56	0.6768 (2)	0.1397 (3)	0.6465 (2)	0.04888
H57	0.0887 (10)	0.7408 (10)	0.5742 (11)	0.05866
H58	0.2582 (8)	0.5519 (11)	0.0640 (9)	0.05866
H59	0.5553 (11)	0.0696 (11)	0.7250 (8)	0.05866
C60	0.7329 (2)	0.2172 (3)	0.6458 (2)	0.04888
C61	0.7070 (3)	0.0395 (3)	0.6663 (2)	0.04888
H62	0.7126 (10)	0.2888 (10)	0.6318 (9)	0.05866
C63	0.8182 (2)	0.1967 (3)	0.6647 (2)	0.04888
C64	0.7908 (2)	0.0153 (3)	0.6852 (2)	0.04888
H65	0.6700 (10)	−0.0166 (10)	0.6674 (9)	0.05866
H66	0.8563 (9)	0.2547 (10)	0.6644 (10)	0.05866
C67	0.8503 (2)	0.0952 (4)	0.6848 (2)	0.04888
H68	0.8068 (10)	−0.0569 (11)	0.6982 (10)	0.05866
Cl69	0.9605 (3)	0.0747 (4)	0.7061 (3)	0.09537

Geometric parameters (Å, º)

Cl69—C67	1.824 (6)	C61—C64	1.404 (6)
O16—C10	1.257 (7)	C63—C67	1.371 (5)
O55—C38	1.415 (7)	C64—C67	1.403 (5)
O55—H59	0.867 (12)	C2—H4	0.997 (14)
N7—C14	1.502 (5)	C2—H5	0.991 (12)
N7—C15	1.509 (5)	C3—H8	0.993 (15)
N7—C3	1.486 (6)	C3—H9	0.999 (12)
N17—C28	1.489 (6)	C14—H23	1.006 (13)
N17—C29	1.539 (7)	C14—H24	1.000 (14)
N17—C10	1.394 (7)	C15—H25	0.974 (12)
N7—H13	0.952 (16)	C15—H26	0.999 (14)
C2—C6	1.559 (6)	C18—H30	0.971 (14)
C2—C3	1.533 (5)	C19—H33	1.002 (17)
C6—C10	1.628 (7)	C20—H34	1.012 (16)
C6—C11	1.524 (6)	C21—H37	0.966 (14)
C6—C12	1.548 (6)	C22—H39	0.989 (14)
C11—C18	1.493 (5)	C22—H40	1.006 (14)
C11—C19	1.435 (5)	C27—H41	0.990 (14)
C12—C21	1.415 (7)	C27—H42	0.998 (14)
C12—C20	1.506 (6)	C28—H43	0.975 (13)
C14—C22	1.579 (6)	C28—H44	0.994 (17)
C15—C27	1.568 (6)	C28—H45	1.000 (17)
C18—C31	1.381 (5)	C29—H46	0.995 (15)
C19—C32	1.375 (5)	C29—H47	1.018 (19)
C20—C35	1.348 (6)	C29—H48	0.991 (13)
C21—C36	1.316 (5)	C31—H49	0.98 (2)
C22—C38	1.574 (6)	C32—H51	0.932 (14)
C27—C38	1.567 (6)	C35—H52	0.976 (14)
C31—C50	1.405 (5)	C36—H54	0.939 (15)
C32—C50	1.476 (5)	C50—H57	0.948 (15)
C35—C53	1.444 (7)	C53—H58	0.950 (13)
C36—C53	1.391 (6)	C60—H62	0.954 (13)
C38—C56	1.514 (6)	C61—H65	0.932 (15)
C56—C61	1.345 (5)	C63—H66	0.960 (14)
C56—C60	1.343 (5)	C64—H68	0.939 (14)
C60—C63	1.419 (5)
C38—O55—H59	108.2 (11)	C2—C3—H8	110.6 (9)
C3—N7—C15	114.0 (3)	C2—C3—H9	109.1 (8)
C14—N7—C15	105.8 (3)	H8—C3—H9	107.0 (12)
C3—N7—C14	115.0 (4)	N7—C14—H23	107.7 (7)
C10—N17—C28	120.3 (4)	N7—C14—H24	108.5 (8)
C28—N17—C29	119.3 (4)	C22—C14—H23	110.6 (9)
C10—N17—C29	120.0 (4)	C22—C14—H24	113.3 (9)
C14—N7—H13	110.0 (9)	H23—C14—H24	107.8 (12)
C3—N7—H13	106.2 (11)	N7—C15—H25	108.5 (9)
C15—N7—H13	105.5 (10)	N7—C15—H26	109.1 (9)
C3—C2—C6	104.1 (3)	C27—C15—H25	111.7 (11)
N7—C3—C2	108.5 (3)	C27—C15—H26	111.1 (9)
C10—C6—C11	118.1 (4)	H25—C15—H26	107.6 (12)
C11—C6—C12	102.3 (3)	C11—C18—H30	122.0 (9)
C2—C6—C11	110.9 (3)	C31—C18—H30	117.2 (9)
C10—C6—C12	106.2 (3)	C11—C19—H33	125.2 (8)
C2—C6—C10	109.8 (3)	C32—C19—H33	122.3 (8)
C2—C6—C12	108.8 (4)	C12—C20—H34	126.2 (8)
O16—C10—N17	116.7 (6)	C35—C20—H34	117.4 (8)
O16—C10—C6	120.1 (5)	C12—C21—H37	123.4 (9)
N17—C10—C6	120.5 (4)	C36—C21—H37	117.4 (9)
C6—C11—C18	119.2 (3)	C14—C22—H39	109.7 (11)
C18—C11—C19	124.4 (3)	C14—C22—H40	111.5 (9)
C6—C11—C19	116.4 (3)	C38—C22—H39	108.9 (9)
C6—C12—C20	120.3 (4)	C38—C22—H40	110.0 (9)
C6—C12—C21	117.9 (4)	H39—C22—H40	106.2 (11)
C20—C12—C21	121.8 (4)	C15—C27—H41	108.6 (9)
N7—C14—C22	108.8 (3)	C15—C27—H42	110.1 (9)
N7—C15—C27	108.9 (3)	C38—C27—H41	107.7 (8)
C11—C18—C31	120.8 (3)	C38—C27—H42	107.7 (8)
C11—C19—C32	112.5 (3)	H41—C27—H42	107.4 (12)
C12—C20—C35	116.4 (4)	N17—C28—H43	110.3 (8)
C12—C21—C36	119.2 (4)	N17—C28—H44	110.0 (8)
C14—C22—C38	110.4 (3)	N17—C28—H45	107.2 (9)
C15—C27—C38	115.1 (4)	H43—C28—H44	106.6 (13)
C18—C31—C50	115.1 (3)	H43—C28—H45	111.1 (12)
C19—C32—C50	123.6 (3)	H44—C28—H45	111.7 (12)
C20—C35—C53	118.8 (4)	N17—C29—H46	109.5 (11)
C21—C36—C53	120.6 (4)	N17—C29—H47	112.6 (9)
O55—C38—C27	102.9 (4)	N17—C29—H48	110.4 (10)
O55—C38—C56	105.5 (4)	H46—C29—H47	106.7 (15)
O55—C38—C22	113.7 (4)	H46—C29—H48	108.1 (11)
C27—C38—C56	107.8 (3)	H47—C29—H48	109.4 (13)
C22—C38—C27	102.2 (3)	C18—C31—H49	122.7 (8)
C22—C38—C56	122.9 (3)	C50—C31—H49	122.1 (8)
C31—C50—C32	123.5 (3)	C19—C32—H51	114.7 (10)
C35—C53—C36	123.2 (3)	C50—C32—H51	121.7 (10)
C38—C56—C61	120.3 (4)	C20—C35—H52	117.9 (9)
C60—C56—C61	115.2 (4)	C53—C35—H52	123.3 (9)
C38—C56—C60	124.5 (3)	C21—C36—H54	117.3 (8)
C56—C60—C63	123.3 (3)	C53—C36—H54	122.1 (8)
C56—C61—C64	123.6 (4)	C31—C50—H57	114.5 (10)
C60—C63—C67	122.5 (3)	C32—C50—H57	122.1 (10)
C61—C64—C67	122.1 (3)	C35—C53—H58	118.8 (9)
Cl69—C67—C64	126.6 (3)	C36—C53—H58	118.0 (9)
C63—C67—C64	113.4 (3)	C56—C60—H62	116.4 (10)
Cl69—C67—C63	120.1 (3)	C63—C60—H62	120.4 (10)
C3—C2—H4	112.6 (8)	C56—C61—H65	117.8 (10)
C3—C2—H5	110.6 (9)	C64—C61—H65	118.6 (10)
C6—C2—H4	110.2 (9)	C60—C63—H66	120.6 (9)
C6—C2—H5	111.7 (10)	C67—C63—H66	116.9 (9)
H4—C2—H5	107.7 (12)	C61—C64—H68	118.2 (11)
N7—C3—H8	110.9 (9)	C67—C64—H68	119.7 (11)
N7—C3—H9	110.7 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H13···Cl1	0.952 (16)	2.278 (16)	3.212 (6)	166.7 (12)
O55—H59···Cl1	0.867 (12)	2.221 (12)	3.069 (7)	165.9 (17)

(II) 6-O-Methylerythromycin A

Crystal data

C38H69NO13	F(000) = 1632.0
Mr = 747.94	Dx = 1.163 Mg m^−3
Orthorhombic, P212121	Cu Kα1 radiation, λ = 1.54056 Å
a = 20.1492 (4) Å	µ = 0.71 mm^−1
b = 23.9545 (5) Å	T = 298 K
c = 8.8534 (2) Å	colourless
V = 4273.25 (16) Å^3	cylinder, 10 × 0.7 mm
Z = 4

Data collection

STOE Stadi-P diffractometer	Data collection mode: transmission
Radiation source: sealed x-ray tube	Scan method: step
Primary focussing Ge 111 monochromator	2θmin = 2.000°, 2θmax = 69.000°, 2θstep = 0.01°
Specimen mounting: glass capillary

Refinement

Least-squares matrix: full with fixed elements per cycle	406 parameters
Rp = 0.021	359 restraints
Rwp = 0.028	0 constraints
Rexp = 0.018	All H-atom parameters refined
RBragg = 0.008	Weighting scheme based on measured s.u.'s
χ^2 = 2.356	(Δ/σ)max = 0.001
6800 data points	Background function: Chebyshev with 20 terms
Profile function: modified Thompson-Cox-Hastings pseudo-Voigt	Preferred orientation correction: none

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.0204 (3)	0.2325 (2)	0.4553 (7)	0.03362
C2	0.0049 (3)	0.2932 (2)	0.4836 (6)	0.03362
C3	0.0073 (3)	0.3256 (2)	0.3327 (6)	0.03362
C4	0.0763 (2)	0.3560 (2)	0.3220 (6)	0.03362
C5	0.0965 (3)	0.3716 (2)	0.1597 (6)	0.03362
C6	0.1307 (3)	0.3232 (2)	0.0647 (6)	0.03362
C7	0.2008 (2)	0.3173 (2)	0.1189 (5)	0.03362
C8	0.2439 (3)	0.2743 (2)	0.0360 (6)	0.03362
C9	0.2310 (4)	0.2128 (2)	0.0764 (6)	0.03362
C10	0.2394 (2)	0.1920 (2)	0.2404 (6)	0.03362
C11	0.1718 (2)	0.1794 (2)	0.3190 (6)	0.03362
C12	0.1732 (3)	0.1685 (2)	0.4879 (6)	0.03362
C13	0.1014 (3)	0.1648 (2)	0.5389 (6)	0.03362
C14	0.0960 (3)	0.1403 (2)	0.6996 (5)	0.03362
C15	0.0271 (2)	0.1346 (2)	0.7615 (5)	0.03362
C16	−0.0609 (3)	0.2952 (2)	0.5558 (5)	0.03362
C17	0.0809 (3)	0.40502 (19)	0.4365 (6)	0.03362
C18	0.1341 (2)	0.33538 (19)	−0.1041 (6)	0.03362
C19	0.3134 (3)	0.29367 (19)	0.0692 (5)	0.03362
C20	0.2853 (2)	0.14103 (19)	0.2347 (6)	0.03362
C21	0.2080 (3)	0.2130 (2)	0.5814 (6)	0.03362
C22	0.0461 (2)	0.2504 (2)	0.0183 (6)	0.03362
O1	0.0044 (4)	0.2064 (3)	0.3396 (8)	0.03362
O2	−0.0489 (3)	0.3670 (3)	0.3338 (7)	0.03362
O3	0.1425 (3)	0.4188 (2)	0.1669 (8)	0.03362
O4	0.1005 (3)	0.2711 (2)	0.1052 (7)	0.03362
O5	0.2020 (4)	0.1842 (3)	−0.0175 (8)	0.03362
O6	0.1393 (4)	0.1337 (3)	0.2461 (7)	0.03362
O7	0.2031 (3)	0.1166 (2)	0.5188 (9)	0.03362
O8	0.0747 (3)	0.2212 (2)	0.5419 (9)	0.03362
C23	0.1240 (3)	0.4700 (2)	0.1039 (6)	0.03362
C24	0.1753 (3)	0.5117 (2)	0.1529 (5)	0.03362
C25	0.1546 (3)	0.5671 (2)	0.0856 (6)	0.03362
C26	0.1548 (3)	0.5623 (2)	−0.0828 (6)	0.03362
C27	0.1036 (3)	0.5192 (2)	−0.1281 (6)	0.03362
C28	0.1050 (2)	0.5096 (2)	−0.2958 (6)	0.03362
C29	0.1660 (2)	0.66466 (19)	0.1489 (6)	0.03362
C30	0.2616 (3)	0.61278 (19)	0.0901 (5)	0.03362
N1	0.1959 (3)	0.6102 (2)	0.1543 (8)	0.03362
O9	0.1756 (4)	0.5156 (2)	0.3127 (6)	0.03362
O10	0.1202 (4)	0.4664 (2)	−0.0536 (6)	0.03362
C31	−0.1006 (3)	0.3637 (2)	0.2216 (6)	0.03362
C32	−0.1579 (2)	0.3996 (2)	0.2698 (6)	0.03362
C33	−0.1501 (2)	0.4621 (2)	0.2488 (6)	0.03362
C34	−0.1307 (3)	0.4708 (2)	0.0845 (6)	0.03362
C35	−0.0717 (3)	0.4337 (2)	0.0345 (6)	0.03362
C36	−0.0587 (3)	0.4301 (2)	−0.1353 (6)	0.03362
C37	−0.2198 (2)	0.4875 (2)	0.2756 (5)	0.03362
C38	−0.1016 (3)	0.4861 (2)	0.4996 (6)	0.03362
O11	−0.0965 (3)	0.4866 (3)	0.3386 (6)	0.03362
O12	−0.1105 (3)	0.5272 (2)	0.0562 (7)	0.03362
O13	−0.0782 (3)	0.3767 (2)	0.0749 (7)	0.03362
H1	0.0398 (8)	0.3095 (8)	0.560 (2)	0.04034
H2	0.0005 (10)	0.2973 (8)	0.252 (2)	0.04034
H3	0.1081 (9)	0.3293 (8)	0.353 (2)	0.04034
H4	0.0587 (8)	0.3812 (9)	0.098 (2)	0.04034
H5	0.2057 (8)	0.3093 (7)	0.241 (2)	0.04034
H6	0.2207 (8)	0.3538 (8)	0.113 (2)	0.04034
H7	0.2319 (8)	0.2779 (8)	−0.069 (2)	0.04034
H8	0.2569 (8)	0.2226 (7)	0.301 (2)	0.04034
H9	0.1453 (10)	0.2097 (8)	0.310 (2)	0.04034
H10	0.0772 (8)	0.1431 (8)	0.463 (2)	0.04034
H11	0.1143 (9)	0.1011 (8)	0.693 (2)	0.04034
H12	0.1188 (10)	0.1650 (8)	0.768 (3)	0.04034
H13	−0.0016 (10)	0.1217 (9)	0.6845 (19)	0.04034
H14	0.0118 (10)	0.1684 (9)	0.815 (2)	0.04034
H15	0.0239 (10)	0.1146 (9)	0.8455 (19)	0.04034
H16	−0.0691 (8)	0.2606 (7)	0.607 (2)	0.04034
H17	−0.0944 (9)	0.2943 (7)	0.472 (2)	0.04034
H18	−0.0696 (8)	0.3271 (8)	0.621 (2)	0.04034
H19	0.0661 (8)	0.3956 (9)	0.535 (2)	0.04034
H20	0.1260 (9)	0.4184 (9)	0.453 (2)	0.04034
H21	0.0549 (8)	0.4393 (9)	0.400 (2)	0.04034
H22	0.1627 (9)	0.3103 (8)	−0.147 (2)	0.04034
H23	0.0904 (9)	0.3326 (8)	−0.143 (2)	0.04034
H24	0.1436 (9)	0.3750 (8)	−0.124 (2)	0.04034
H25	0.3142 (9)	0.3298 (8)	0.034 (2)	0.04034
H26	0.3427 (9)	0.2688 (8)	−0.001 (2)	0.04034
H27	0.3274 (9)	0.2878 (8)	0.190 (2)	0.04034
H28	0.2618 (7)	0.1093 (8)	0.178 (2)	0.04034
H29	0.2940 (8)	0.1331 (8)	0.332 (2)	0.04034
H30	0.3309 (9)	0.1525 (8)	0.202 (2)	0.04034
H31	0.1968 (8)	0.2119 (8)	0.690 (2)	0.04034
H32	0.2024 (8)	0.2493 (7)	0.539 (2)	0.04034
H33	0.2545 (9)	0.2063 (8)	0.574 (2)	0.04034
H34	0.0221 (9)	0.2252 (7)	0.096 (2)	0.04034
H35	0.0581 (8)	0.2346 (8)	−0.068 (2)	0.04034
H36	0.0141 (9)	0.2815 (8)	−0.008 (2)	0.04034
H37	0.1376 (11)	0.1433 (8)	0.151 (2)	0.04034
H38	0.1735 (8)	0.0939 (7)	0.518 (4)	0.04034
H39	0.0809 (8)	0.4827 (7)	0.145 (2)	0.04034
H40	0.2261 (9)	0.4981 (7)	0.120 (3)	0.04034
H41	0.1097 (9)	0.5741 (9)	0.116 (2)	0.04034
H42	0.1462 (10)	0.5961 (8)	−0.134 (2)	0.04034
H43	0.2032 (9)	0.5529 (9)	−0.121 (2)	0.04034
H44	0.0556 (8)	0.5310 (7)	−0.099 (2)	0.04034
H45	0.1525 (10)	0.5010 (7)	−0.332 (2)	0.04034
H46	0.0783 (8)	0.4782 (7)	−0.319 (2)	0.04034
H47	0.0828 (8)	0.5439 (8)	−0.350 (2)	0.04034
H48	0.1201 (9)	0.6612 (8)	0.150 (2)	0.04034
H49	0.1805 (9)	0.6900 (8)	0.237 (2)	0.04034
H50	0.1824 (8)	0.6860 (8)	0.044 (2)	0.04034
H51	0.2932 (8)	0.6243 (8)	0.1704 (19)	0.04034
H52	0.2758 (8)	0.5760 (8)	0.060 (2)	0.04034
H53	0.2621 (8)	0.6391 (7)	−0.000 (2)	0.04034
H54	0.1726 (15)	0.5488 (8)	0.336 (2)	0.04034
H55	−0.1165 (9)	0.3240 (8)	0.209 (2)	0.04034
H56	−0.1983 (9)	0.3889 (8)	0.208 (2)	0.04034
H57	−0.1721 (9)	0.3941 (7)	0.375 (2)	0.04034
H58	−0.1717 (9)	0.4640 (7)	0.018 (2)	0.04034
H59	−0.0319 (9)	0.4473 (9)	0.0846 (19)	0.04034
H60	−0.0684 (8)	0.4630 (8)	−0.176 (2)	0.04034
H61	−0.0815 (9)	0.4004 (9)	−0.175 (2)	0.04034
H62	−0.0142 (10)	0.4148 (9)	−0.1555 (19)	0.04034
H63	−0.2499 (9)	0.4655 (8)	0.211 (3)	0.04034
H64	−0.2305 (9)	0.4866 (7)	0.402 (3)	0.04034
H65	−0.2210 (9)	0.5258 (7)	0.255 (2)	0.04034
H66	−0.0533 (8)	0.5015 (7)	0.535 (2)	0.04034
H67	−0.1125 (9)	0.4530 (8)	0.536 (2)	0.04034
H68	−0.1262 (10)	0.5151 (7)	0.549 (2)	0.04034
H69	−0.0865 (11)	0.5352 (7)	0.140 (2)	0.04034

Geometric parameters (Å, º)

O1—C1	1.243 (9)	C7—H5	1.102 (18)
O2—C3	1.505 (9)	C7—H6	0.963 (19)
O2—C31	1.442 (8)	C8—H7	0.964 (18)
O3—C5	1.463 (8)	C10—H8	0.974 (18)
O3—C23	1.398 (7)	C11—H9	0.91 (2)
O4—C6	1.434 (7)	C13—H10	0.980 (18)
O4—C22	1.428 (7)	C14—H11	1.01 (2)
O5—C9	1.226 (9)	C14—H12	0.96 (2)
O6—C11	1.430 (8)	C15—H13	0.946 (19)
O7—C12	1.408 (7)	C15—H14	0.99 (2)
O8—C1	1.363 (9)	C15—H15	0.887 (19)
O8—C13	1.455 (7)	C16—H16	0.959 (18)
O9—C24	1.418 (7)	C16—H17	1.003 (19)
O10—C23	1.399 (8)	C16—H18	0.974 (19)
O10—C27	1.465 (7)	C17—H19	0.949 (18)
O11—C33	1.464 (8)	C17—H20	0.98 (2)
O11—C38	1.429 (8)	C17—H21	1.03 (2)
O12—C34	1.433 (7)	C18—H22	0.915 (19)
O13—C31	1.410 (8)	C18—H23	0.948 (18)
O13—C35	1.418 (7)	C18—H24	0.98 (2)
O6—H37	0.874 (19)	C19—H25	0.92 (2)
O7—H38	0.807 (17)	C19—H26	1.044 (19)
O9—H54	0.82 (2)	C19—H27	1.115 (18)
O12—H69	0.91 (2)	C20—H28	1.027 (18)
N1—C29	1.438 (7)	C20—H29	0.899 (18)
N1—C30	1.442 (9)	C20—H30	1.002 (19)
N1—C25	1.459 (8)	C21—H31	0.988 (18)
C1—C2	1.508 (7)	C21—H32	0.954 (18)
C2—C16	1.473 (8)	C21—H33	0.953 (19)
C2—C3	1.546 (7)	C22—H34	1.035 (18)
C3—C4	1.572 (7)	C22—H35	0.886 (18)
C4—C17	1.554 (7)	C22—H36	1.012 (19)
C4—C5	1.540 (7)	C23—H39	0.990 (17)
C5—C6	1.590 (7)	C24—H40	1.11 (2)
C6—C7	1.498 (7)	C25—H41	0.959 (19)
C6—C18	1.524 (7)	C26—H42	0.944 (19)
C7—C8	1.534 (7)	C26—H43	1.057 (19)
C8—C9	1.538 (7)	C27—H44	1.040 (17)
C8—C19	1.504 (8)	C28—H45	1.03 (2)
C9—C10	1.544 (7)	C28—H46	0.947 (17)
C10—C20	1.533 (6)	C28—H47	1.051 (19)
C10—C11	1.559 (6)	C29—H48	0.929 (19)
C11—C12	1.518 (7)	C29—H49	1.031 (19)
C12—C13	1.518 (8)	C29—H50	1.110 (19)
C12—C21	1.521 (7)	C30—H51	0.994 (18)
C13—C14	1.543 (6)	C30—H52	0.964 (19)
C14—C15	1.499 (7)	C30—H53	1.017 (18)
C23—C24	1.502 (8)	C31—H55	1.01 (2)
C24—C25	1.513 (7)	C32—H56	1.014 (18)
C25—C26	1.495 (8)	C32—H57	0.983 (18)
C26—C27	1.514 (8)	C34—H58	1.027 (19)
C27—C28	1.503 (7)	C35—H59	0.973 (19)
C31—C32	1.502 (7)	C36—H60	0.888 (19)
C32—C33	1.517 (7)	C36—H61	0.92 (2)
C33—C37	1.549 (6)	C36—H62	0.99 (2)
C33—C34	1.521 (7)	C37—H63	0.986 (19)
C34—C35	1.549 (8)	C37—H64	1.14 (3)
C35—C36	1.528 (8)	C37—H65	0.936 (17)
C2—H1	1.051 (18)	C38—H66	1.087 (17)
C3—H2	0.994 (19)	C38—H67	0.88 (2)
C4—H3	0.946 (19)	C38—H68	0.959 (19)
C5—H4	0.965 (18)
C3—O2—C31	120.2 (5)	C15—C14—H11	105.9 (11)
C5—O3—C23	119.4 (5)	C15—C14—H12	105.5 (12)
C6—O4—C22	119.6 (5)	H11—C14—H12	115.7 (16)
C1—O8—C13	118.1 (5)	C14—C15—H13	109.4 (12)
C23—O10—C27	114.1 (4)	C14—C15—H14	113.0 (12)
C33—O11—C38	119.0 (5)	C14—C15—H15	115.0 (14)
C31—O13—C35	118.4 (5)	H13—C15—H14	115.0 (18)
C11—O6—H37	104.6 (14)	H13—C15—H15	112.5 (18)
C12—O7—H38	106.1 (14)	H14—C15—H15	91.0 (18)
C24—O9—H54	108.3 (13)	C2—C16—H16	109.4 (11)
C34—O12—H69	102.0 (12)	C2—C16—H17	106.5 (11)
C29—N1—C30	109.4 (4)	C2—C16—H18	116.4 (11)
C25—N1—C29	112.9 (5)	H16—C16—H17	102.4 (15)
C25—N1—C30	112.9 (5)	H16—C16—H18	111.5 (15)
O1—C1—C2	124.6 (6)	H17—C16—H18	109.5 (15)
O8—C1—C2	105.3 (5)	C4—C17—H19	113.7 (13)
O1—C1—O8	124.9 (6)	C4—C17—H20	113.7 (12)
C1—C2—C3	109.5 (4)	C4—C17—H21	111.6 (11)
C1—C2—C16	106.9 (4)	H19—C17—H20	103.5 (15)
C3—C2—C16	112.8 (5)	H19—C17—H21	108.6 (16)
O2—C3—C4	111.1 (4)	H20—C17—H21	105.1 (16)
C2—C3—C4	108.2 (4)	C6—C18—H22	108.0 (12)
O2—C3—C2	107.6 (5)	C6—C18—H23	107.5 (12)
C3—C4—C5	113.7 (4)	C6—C18—H24	111.7 (11)
C5—C4—C17	114.2 (4)	H22—C18—H23	112.8 (17)
C3—C4—C17	111.3 (4)	H22—C18—H24	115.9 (16)
O3—C5—C6	108.2 (5)	H23—C18—H24	100.6 (16)
O3—C5—C4	108.3 (5)	C8—C19—H25	103.9 (12)
C4—C5—C6	115.6 (4)	C8—C19—H26	103.5 (11)
O4—C6—C7	103.8 (4)	C8—C19—H27	112.6 (10)
O4—C6—C18	115.5 (5)	H25—C19—H26	109.0 (16)
C5—C6—C7	107.9 (4)	H25—C19—H27	116.1 (16)
C5—C6—C18	113.5 (4)	H26—C19—H27	110.9 (15)
O4—C6—C5	108.6 (5)	C10—C20—H28	109.1 (10)
C7—C6—C18	106.8 (4)	C10—C20—H29	104.7 (12)
C6—C7—C8	116.3 (4)	C10—C20—H30	110.2 (12)
C7—C8—C9	115.9 (5)	H28—C20—H29	113.7 (16)
C9—C8—C19	114.0 (5)	H28—C20—H30	119.0 (14)
C7—C8—C19	103.1 (4)	H29—C20—H30	99.0 (15)
O5—C9—C8	117.3 (6)	C12—C21—H31	113.9 (11)
O5—C9—C10	120.6 (5)	C12—C21—H32	111.7 (11)
C8—C9—C10	120.6 (4)	C12—C21—H33	107.3 (12)
C11—C10—C20	112.8 (4)	H31—C21—H32	112.4 (16)
C9—C10—C11	112.7 (4)	H31—C21—H33	106.7 (15)
C9—C10—C20	107.0 (4)	H32—C21—H33	104.1 (16)
O6—C11—C12	108.8 (4)	O4—C22—H34	101.7 (11)
C10—C11—C12	117.2 (4)	O4—C22—H35	113.8 (11)
O6—C11—C10	110.3 (4)	O4—C22—H36	110.9 (11)
O7—C12—C11	110.6 (5)	H34—C22—H35	116.8 (16)
C13—C12—C21	108.6 (4)	H34—C22—H36	106.5 (15)
O7—C12—C21	108.4 (5)	H35—C22—H36	106.8 (16)
C11—C12—C13	106.6 (4)	O3—C23—H39	110.9 (11)
O7—C12—C13	107.4 (5)	O10—C23—H39	109.7 (12)
C11—C12—C21	115.1 (4)	C24—C23—H39	107.1 (11)
O8—C13—C12	107.7 (4)	O9—C24—H40	106.1 (14)
O8—C13—C14	108.1 (5)	C23—C24—H40	111.3 (11)
C12—C13—C14	111.3 (5)	C25—C24—H40	114.0 (11)
C13—C14—C15	115.9 (5)	N1—C25—H41	107.3 (13)
O3—C23—C24	106.6 (5)	C24—C25—H41	107.6 (13)
O10—C23—C24	111.5 (5)	C26—C25—H41	107.2 (12)
O3—C23—O10	111.0 (5)	C25—C26—H42	114.4 (12)
O9—C24—C25	109.7 (4)	C25—C26—H43	109.8 (11)
C23—C24—C25	106.3 (4)	C27—C26—H42	109.4 (13)
O9—C24—C23	109.6 (5)	C27—C26—H43	113.5 (12)
N1—C25—C24	107.4 (5)	H42—C26—H43	101.5 (17)
N1—C25—C26	117.9 (5)	O10—C27—H44	109.6 (11)
C24—C25—C26	108.9 (4)	C26—C27—H44	112.5 (10)
C25—C26—C27	108.4 (4)	C28—C27—H44	107.7 (11)
O10—C27—C28	108.0 (4)	C27—C28—H45	110.8 (11)
C26—C27—C28	110.7 (4)	C27—C28—H46	109.0 (12)
O10—C27—C26	108.3 (5)	C27—C28—H47	108.9 (11)
O2—C31—O13	113.0 (5)	H45—C28—H46	107.5 (15)
O2—C31—C32	109.2 (5)	H45—C28—H47	114.2 (14)
O13—C31—C32	112.4 (5)	H46—C28—H47	106.3 (15)
C31—C32—C33	116.8 (4)	N1—C29—H48	109.6 (13)
O11—C33—C34	106.0 (4)	N1—C29—H49	113.0 (11)
O11—C33—C37	115.4 (4)	N1—C29—H50	108.7 (10)
C32—C33—C34	106.2 (4)	H48—C29—H49	109.1 (16)
C32—C33—C37	106.0 (3)	H48—C29—H50	110.3 (15)
O11—C33—C32	113.9 (4)	H49—C29—H50	106.1 (14)
C34—C33—C37	109.0 (4)	N1—C30—H51	108.6 (10)
O12—C34—C33	111.7 (4)	N1—C30—H52	110.0 (11)
O12—C34—C35	105.8 (5)	N1—C30—H53	110.2 (10)
C33—C34—C35	113.1 (4)	H51—C30—H52	105.2 (15)
O13—C35—C36	102.1 (4)	H51—C30—H53	112.5 (15)
C34—C35—C36	116.4 (4)	H52—C30—H53	110.3 (15)
O13—C35—C34	114.2 (5)	O2—C31—H55	110.9 (11)
C1—C2—H1	109.1 (11)	O13—C31—H55	102.0 (11)
C3—C2—H1	110.4 (11)	C32—C31—H55	109.1 (12)
C16—C2—H1	108.1 (10)	C31—C32—H56	108.6 (11)
O2—C3—H2	110.5 (13)	C31—C32—H57	114.6 (11)
C2—C3—H2	105.9 (12)	C33—C32—H56	105.5 (12)
C4—C3—H2	113.2 (12)	C33—C32—H57	106.2 (11)
C3—C4—H3	105.6 (12)	H56—C32—H57	104.1 (15)
C5—C4—H3	104.8 (12)	O12—C34—H58	106.1 (11)
C17—C4—H3	106.3 (12)	C33—C34—H58	108.7 (11)
O3—C5—H4	109.9 (13)	C35—C34—H58	111.3 (11)
C4—C5—H4	112.2 (11)	O13—C35—H59	106.5 (13)
C6—C5—H4	102.5 (12)	C34—C35—H59	108.1 (12)
C6—C7—H5	114.5 (9)	C36—C35—H59	109.0 (11)
C6—C7—H6	106.8 (11)	C35—C36—H60	108.1 (12)
C8—C7—H5	107.6 (9)	C35—C36—H61	109.6 (12)
C8—C7—H6	110.4 (11)	C35—C36—H62	110.8 (11)
H5—C7—H6	100.0 (14)	H60—C36—H61	115.0 (18)
C7—C8—H7	105.0 (12)	H60—C36—H62	117.2 (17)
C9—C8—H7	105.5 (12)	H61—C36—H62	95.6 (18)
C19—C8—H7	113.2 (11)	C33—C37—H63	105.0 (11)
C9—C10—H8	108.3 (11)	C33—C37—H64	108.3 (10)
C11—C10—H8	102.5 (11)	C33—C37—H65	112.3 (12)
C20—C10—H8	113.5 (10)	H63—C37—H64	116.3 (14)
O6—C11—H9	107.7 (13)	H63—C37—H65	113.3 (16)
C10—C11—H9	108.7 (13)	H64—C37—H65	101.8 (14)
C12—C11—H9	103.6 (12)	O11—C38—H66	102.7 (10)
O8—C13—H10	108.7 (12)	O11—C38—H67	112.9 (13)
C12—C13—H10	107.5 (11)	O11—C38—H68	119.1 (12)
C14—C13—H10	113.3 (12)	H66—C38—H67	115.0 (16)
C13—C14—H11	105.9 (11)	H66—C38—H68	94.9 (15)
C13—C14—H12	108.2 (12)	H67—C38—H68	110.8 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H37···O5	0.874 (19)	2.21 (2)	2.917 (10)	138.2 (19)
O7—H38···O12	0.807 (17)	2.14 (2)	2.917 (8)	161 (3)
O9—H54···N1	0.82 (2)	2.23 (2)	2.696 (7)	116.2 (16)
O12—H69···O11	0.91 (2)	2.118 (18)	2.698 (8)	120.8 (16)