3,3′-(3,6-Dihydr­oxy-p-phenyl­ene)bis­(4,7-dihydr­oxy-2H-chromen-2-one) dimethyl­formamide tris­olvate

The two chromen-3-yl substituents at the 2- and 3-positions of the 1,4-dihydroxy­benzene in the title dimethyl­formamide (DMF) tris­olvate, C₂₄H₁₄O₁₀·3C₃H₇NO, are aligned at 67.1 (1) and 69.8 (1)° with respect to the central aromatic ring. The 1-hydr­oxy group serves as a hydrogen-bond donor to a DMF whereas the substituent at the 3-position functions as a hydrogen-bond donor to two DMF mol­ecules. The other three hydr­oxy groups inter­act with donor sites of adjacent mol­ecules, generating a three-dimensional network architecture.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.062
• wR factor = 0.164
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT223_ALERT_4_B Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       4.89 Ratio

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT221_ALERT_4_C Large Solvent/Anion  C     Ueq(max)/Ueq(min) ...       3.92 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C32'
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N2
PLAT301_ALERT_3_C Main Residue  Disorder .........................      11.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O13    ..  C17     ..       2.96 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C17    ..  C31'    ..       3.19 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O10  -H10O    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O10  -H10O    1.555   1.555

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

3,3'-(3,6-dihydroxy-p-phenylene)bis(4,7-dihydroxy-2H-chromen-2-one) dimethylformamide trisolvate

Crystal data

C24H14O10·3C3H7NO	F(000) = 1432
Mr = 681.64	Dx = 1.390 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4459 reflections
a = 11.3725 (6) Å	θ = 2.2–22.4°
b = 14.0520 (8) Å	µ = 0.11 mm^−1
c = 20.535 (1) Å	T = 123 K
β = 97.058 (1)°	Block, brown
V = 3256.7 (3) Å^3	0.35 × 0.25 × 0.20 mm
Z = 4

Data collection

Bruker SMART area-detector diffractometer	4883 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
Graphite monochromator	θmax = 27.0°, θmin = 1.8°
φ and ω scans	h = −14→14
25715 measured reflections	k = −17→17
6956 independent reflections	l = −26→26

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0791P)^2 + 1.3446P] where P = (Fo^2 + 2Fc^2)/3
6956 reflections	(Δ/σ)max = 0.001
510 parameters	Δρmax = 0.31 e Å^−3
76 restraints	Δρmin = −0.29 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.60558 (15)	0.29605 (13)	0.70280 (8)	0.0341 (4)
O2	0.51452 (15)	0.22270 (12)	0.61668 (8)	0.0332 (4)
O3	0.32861 (15)	0.25666 (12)	0.80983 (8)	0.0317 (4)
O4	0.83675 (18)	0.43012 (16)	0.88390 (10)	0.0514 (6)
O5	0.36057 (16)	0.04980 (12)	0.74785 (8)	0.0346 (4)
O6	0.06222 (17)	0.19951 (14)	0.54061 (9)	0.0427 (5)
O7	0.25738 (16)	0.48333 (11)	0.62326 (8)	0.0337 (4)
O8	0.19847 (15)	0.38476 (11)	0.69521 (8)	0.0307 (4)
O9	0.32762 (16)	0.26744 (12)	0.49921 (8)	0.0336 (4)
O10	0.3662 (2)	0.71407 (13)	0.47855 (11)	0.0549 (6)
O11	0.85837 (17)	0.41816 (12)	1.01301 (8)	0.0402 (5)
O12	0.11676 (16)	0.19670 (14)	0.78736 (9)	0.0419 (5)
N1	0.8491 (2)	0.56377 (15)	1.05805 (11)	0.0391 (5)
N2	−0.0595 (2)	0.15661 (19)	0.73196 (12)	0.0491 (6)
C1	0.6144 (2)	0.32256 (17)	0.76754 (11)	0.0305 (5)
C2	0.7200 (2)	0.36250 (19)	0.79448 (13)	0.0391 (6)
H2	0.7831	0.3709	0.7687	0.047*
C3	0.7327 (2)	0.39011 (19)	0.85925 (13)	0.0374 (6)
C4	0.6400 (2)	0.37653 (18)	0.89737 (12)	0.0348 (6)
H4	0.6495	0.3946	0.9423	0.042*
C5	0.5358 (2)	0.33713 (16)	0.86967 (12)	0.0311 (5)
H5	0.4729	0.3285	0.8955	0.037*
C6	0.5207 (2)	0.30939 (16)	0.80373 (11)	0.0284 (5)
C7	0.4143 (2)	0.26415 (16)	0.77240 (11)	0.0269 (5)
C8	0.4097 (2)	0.23166 (16)	0.70897 (11)	0.0263 (5)
C9	0.5080 (2)	0.24778 (16)	0.67309 (11)	0.0287 (5)
C10	0.3071 (2)	0.17741 (16)	0.67573 (11)	0.0256 (5)
C11	0.2845 (2)	0.08565 (16)	0.69724 (11)	0.0275 (5)
C12	0.1892 (2)	0.03445 (17)	0.66658 (12)	0.0311 (5)
H12	0.1735	−0.0278	0.6814	0.037*
C13	0.1170 (2)	0.07374 (17)	0.61454 (12)	0.0326 (6)
H13	0.0521	0.0380	0.5937	0.039*
C14	0.1378 (2)	0.16474 (17)	0.59225 (12)	0.0301 (5)
C15	0.2343 (2)	0.21661 (16)	0.62239 (11)	0.0261 (5)
C16	0.2590 (2)	0.31440 (16)	0.59975 (11)	0.0256 (5)
C17	0.2358 (2)	0.39185 (16)	0.64216 (11)	0.0267 (5)
C18	0.3004 (2)	0.33312 (16)	0.54116 (11)	0.0274 (5)
C19	0.3166 (2)	0.42991 (16)	0.52104 (11)	0.0269 (5)
C20	0.3578 (2)	0.45543 (17)	0.46157 (11)	0.0288 (5)
H20	0.3747	0.4072	0.4317	0.035*
C21	0.3740 (2)	0.54908 (17)	0.44623 (12)	0.0316 (5)
H21	0.4006	0.5655	0.4056	0.038*
C22	0.3510 (2)	0.62056 (17)	0.49056 (13)	0.0364 (6)
C23	0.3118 (2)	0.59746 (17)	0.54959 (13)	0.0385 (6)
H23	0.2967	0.6457	0.5799	0.046*
C24	0.2950 (2)	0.50273 (17)	0.56361 (11)	0.0300 (5)
C25	0.8897 (2)	0.47648 (18)	1.05697 (12)	0.0342 (6)
H25	0.9468	0.4568	1.0921	0.041*
C26	0.7550 (3)	0.5948 (2)	1.00758 (18)	0.0621 (9)
H26A	0.6893	0.5492	1.0048	0.093*
H26B	0.7858	0.5981	0.9651	0.093*
H26C	0.7267	0.6578	1.0190	0.093*
C27	0.8884 (3)	0.6290 (2)	1.11093 (15)	0.0498 (7)
H27A	0.9466	0.5971	1.1429	0.075*
H27B	0.8204	0.6490	1.1326	0.075*
H27C	0.9250	0.6849	1.0931	0.075*
C28	0.0405 (2)	0.20466 (19)	0.74002 (14)	0.0372 (6)
H28	0.0547	0.2487	0.7068	0.045*
C29	−0.0798 (5)	0.0867 (5)	0.7803 (2)	0.147 (3)
H29A	−0.0108	0.0838	0.8139	0.220*
H29B	−0.0923	0.0243	0.7592	0.220*
H29C	−0.1502	0.1043	0.8008	0.220*
C30	−0.1424 (3)	0.1623 (3)	0.67247 (17)	0.0601 (9)
H30A	−0.1142	0.2094	0.6428	0.090*
H30B	−0.2204	0.1815	0.6835	0.090*
H30C	−0.1485	0.1000	0.6509	0.090*
O13	0.0063 (4)	0.3976 (4)	0.5566 (2)	0.0512 (12)	0.50
N3	−0.06029 (19)	0.5059 (2)	0.61834 (11)	0.0514 (6)	0.50
C31	−0.0549 (6)	0.4242 (6)	0.5997 (3)	0.055 (3)	0.50
H31	−0.1000	0.3775	0.6191	0.067*	0.50
C32	−0.1291 (5)	0.5448 (5)	0.6703 (3)	0.0578 (17)	0.50
H32A	−0.1810	0.4951	0.6843	0.087*	0.50
H32B	−0.1772	0.5989	0.6526	0.087*	0.50
H32C	−0.0741	0.5658	0.7080	0.087*	0.50
C33	0.0058 (6)	0.5874 (5)	0.5933 (4)	0.0493 (19)	0.50
H33A	0.0575	0.5638	0.5621	0.074*	0.50
H33B	0.0539	0.6185	0.6301	0.074*	0.50
H33C	−0.0507	0.6333	0.5714	0.074*	0.50
O13'	−0.0360 (4)	0.3479 (3)	0.5785 (2)	0.0571 (12)	0.50
N3'	−0.06029 (19)	0.5059 (2)	0.61834 (11)	0.0514 (6)	0.50
C31'	−0.0275 (5)	0.4364 (5)	0.5764 (4)	0.052 (2)	0.50
H31'	0.0074	0.4600	0.5399	0.063*	0.50
C32'	−0.0456 (7)	0.6027 (5)	0.6080 (4)	0.068 (3)	0.50
H32D	−0.0291	0.6132	0.5628	0.102*	0.50
H32E	0.0208	0.6264	0.6386	0.102*	0.50
H32F	−0.1182	0.6366	0.6152	0.102*	0.50
C33'	−0.1145 (6)	0.4656 (6)	0.6730 (3)	0.0592 (17)	0.50
H33D	−0.0938	0.3980	0.6778	0.089*	0.50
H33E	−0.2008	0.4723	0.6645	0.089*	0.50
H33F	−0.0852	0.4994	0.7135	0.089*	0.50
H3O	0.2600 (15)	0.237 (2)	0.7932 (14)	0.054 (9)*
H4O	0.845 (3)	0.432 (2)	0.9256 (5)	0.063 (11)*
H5O	0.334 (3)	−0.0009 (14)	0.7629 (15)	0.060 (10)*
H6O	0.041 (3)	0.2560 (11)	0.5476 (17)	0.067 (11)*
H9O	0.338 (3)	0.2114 (12)	0.5152 (16)	0.070 (11)*
H10O	0.401 (3)	0.717 (3)	0.4442 (11)	0.075 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0342 (9)	0.0408 (10)	0.0278 (9)	−0.0079 (8)	0.0059 (7)	0.0017 (7)
O2	0.0391 (10)	0.0350 (10)	0.0269 (9)	−0.0044 (8)	0.0092 (7)	0.0002 (7)
O3	0.0304 (10)	0.0373 (10)	0.0280 (9)	−0.0053 (8)	0.0059 (7)	−0.0043 (7)
O4	0.0461 (12)	0.0698 (15)	0.0364 (12)	−0.0261 (10)	−0.0020 (9)	0.0021 (10)
O5	0.0428 (10)	0.0268 (9)	0.0340 (9)	−0.0044 (8)	0.0042 (8)	0.0088 (7)
O6	0.0440 (11)	0.0373 (11)	0.0431 (11)	−0.0025 (9)	−0.0092 (9)	0.0019 (9)
O7	0.0510 (11)	0.0212 (8)	0.0319 (9)	−0.0014 (7)	0.0173 (8)	−0.0014 (7)
O8	0.0416 (10)	0.0239 (8)	0.0282 (9)	−0.0006 (7)	0.0107 (7)	−0.0015 (7)
O9	0.0515 (11)	0.0229 (9)	0.0272 (9)	0.0025 (8)	0.0078 (8)	−0.0017 (7)
O10	0.0937 (17)	0.0250 (10)	0.0553 (13)	−0.0003 (10)	0.0465 (12)	0.0037 (9)
O11	0.0581 (12)	0.0284 (9)	0.0330 (10)	−0.0065 (8)	0.0017 (9)	0.0008 (8)
O12	0.0397 (10)	0.0502 (11)	0.0369 (10)	−0.0124 (9)	0.0088 (9)	−0.0075 (9)
N1	0.0431 (13)	0.0293 (12)	0.0449 (13)	−0.0059 (10)	0.0048 (10)	−0.0001 (10)
N2	0.0411 (14)	0.0630 (16)	0.0445 (14)	−0.0168 (12)	0.0104 (11)	−0.0123 (12)
C1	0.0353 (13)	0.0286 (13)	0.0268 (12)	−0.0025 (10)	0.0006 (10)	0.0056 (10)
C2	0.0363 (15)	0.0481 (16)	0.0336 (14)	−0.0102 (12)	0.0065 (11)	0.0078 (12)
C3	0.0389 (15)	0.0367 (14)	0.0347 (14)	−0.0106 (12)	−0.0029 (11)	0.0053 (11)
C4	0.0429 (15)	0.0308 (13)	0.0298 (13)	−0.0020 (11)	0.0010 (11)	0.0026 (10)
C5	0.0363 (14)	0.0260 (12)	0.0313 (13)	0.0002 (10)	0.0045 (10)	0.0026 (10)
C6	0.0336 (13)	0.0213 (11)	0.0300 (12)	0.0012 (10)	0.0031 (10)	0.0035 (9)
C7	0.0312 (13)	0.0226 (11)	0.0275 (12)	0.0023 (9)	0.0058 (10)	0.0047 (9)
C8	0.0313 (13)	0.0209 (11)	0.0271 (12)	−0.0004 (9)	0.0043 (10)	0.0037 (9)
C9	0.0332 (13)	0.0244 (12)	0.0280 (13)	−0.0008 (10)	0.0024 (10)	0.0042 (9)
C10	0.0294 (12)	0.0234 (12)	0.0251 (12)	−0.0009 (9)	0.0078 (9)	−0.0034 (9)
C11	0.0345 (13)	0.0244 (12)	0.0249 (12)	0.0022 (10)	0.0096 (10)	−0.0004 (9)
C12	0.0388 (14)	0.0207 (11)	0.0353 (13)	−0.0045 (10)	0.0111 (11)	−0.0015 (10)
C13	0.0332 (13)	0.0284 (13)	0.0366 (14)	−0.0057 (10)	0.0064 (11)	−0.0074 (10)
C14	0.0327 (13)	0.0304 (13)	0.0274 (12)	0.0012 (10)	0.0040 (10)	−0.0028 (10)
C15	0.0311 (13)	0.0230 (12)	0.0253 (12)	0.0006 (9)	0.0079 (10)	−0.0015 (9)
C16	0.0283 (12)	0.0211 (11)	0.0269 (12)	−0.0005 (9)	0.0018 (9)	−0.0003 (9)
C17	0.0313 (13)	0.0220 (11)	0.0269 (12)	−0.0005 (9)	0.0042 (10)	0.0007 (9)
C18	0.0304 (12)	0.0248 (12)	0.0267 (12)	0.0016 (9)	0.0023 (10)	−0.0038 (9)
C19	0.0302 (12)	0.0265 (12)	0.0237 (12)	0.0014 (9)	0.0012 (9)	0.0019 (9)
C20	0.0345 (13)	0.0278 (12)	0.0240 (12)	0.0021 (10)	0.0028 (10)	−0.0020 (9)
C21	0.0336 (13)	0.0344 (14)	0.0275 (12)	0.0005 (11)	0.0061 (10)	0.0034 (10)
C22	0.0465 (16)	0.0242 (13)	0.0406 (15)	0.0015 (11)	0.0136 (12)	0.0032 (11)
C23	0.0575 (17)	0.0216 (12)	0.0406 (15)	−0.0002 (12)	0.0222 (13)	−0.0020 (10)
C24	0.0369 (13)	0.0273 (12)	0.0272 (12)	0.0013 (10)	0.0090 (10)	0.0016 (10)
C25	0.0373 (14)	0.0338 (14)	0.0323 (14)	−0.0075 (11)	0.0073 (11)	0.0011 (11)
C26	0.068 (2)	0.0352 (17)	0.077 (2)	−0.0036 (15)	−0.0142 (18)	0.0076 (15)
C27	0.0566 (19)	0.0372 (16)	0.0573 (19)	−0.0071 (14)	0.0133 (15)	−0.0117 (14)
C28	0.0394 (15)	0.0342 (14)	0.0394 (15)	−0.0045 (11)	0.0102 (12)	−0.0104 (11)
C29	0.147 (5)	0.206 (7)	0.079 (3)	−0.134 (5)	−0.013 (3)	0.042 (4)
C30	0.0397 (17)	0.074 (2)	0.065 (2)	−0.0026 (16)	−0.0011 (15)	−0.0196 (18)
O13	0.053 (3)	0.037 (3)	0.060 (3)	0.005 (2)	−0.005 (2)	−0.003 (2)
N3	0.0428 (14)	0.0642 (18)	0.0467 (14)	0.0051 (12)	0.0030 (11)	0.0026 (13)
C31	0.043 (4)	0.039 (5)	0.080 (6)	0.000 (3)	−0.008 (4)	0.002 (4)
C32	0.047 (4)	0.070 (4)	0.056 (4)	0.011 (3)	0.005 (3)	−0.003 (3)
C33	0.060 (4)	0.034 (3)	0.051 (4)	0.016 (3)	−0.003 (3)	−0.012 (3)
O13'	0.060 (3)	0.044 (3)	0.067 (3)	0.010 (2)	0.004 (2)	−0.003 (2)
N3'	0.0428 (14)	0.0642 (18)	0.0467 (14)	0.0051 (12)	0.0030 (11)	0.0026 (13)
C31'	0.043 (4)	0.050 (5)	0.061 (5)	−0.003 (4)	−0.006 (4)	−0.004 (4)
C32'	0.090 (6)	0.034 (4)	0.072 (5)	0.007 (4)	−0.014 (5)	−0.012 (3)
C33'	0.051 (4)	0.073 (4)	0.055 (4)	0.008 (3)	0.010 (3)	−0.003 (3)

Geometric parameters (Å, º)

O1—C1	1.372 (3)	C15—C16	1.488 (3)
O1—C9	1.377 (3)	C16—C18	1.371 (3)
O2—C9	1.222 (3)	C16—C17	1.438 (3)
O3—C7	1.318 (3)	C18—C19	1.440 (3)
O3—H3O	0.857 (10)	C19—C24	1.387 (3)
O4—C3	1.351 (3)	C19—C20	1.407 (3)
O4—H4O	0.850 (10)	C20—C21	1.371 (3)
O5—C11	1.364 (3)	C20—H20	0.9500
O5—H5O	0.849 (10)	C21—C22	1.402 (3)
O6—C14	1.370 (3)	C21—H21	0.9500
O6—H6O	0.848 (10)	C22—C23	1.381 (4)
O7—C24	1.374 (3)	C23—C24	1.380 (3)
O7—C17	1.373 (3)	C23—H23	0.9500
O8—C17	1.221 (3)	C25—H25	0.9500
O9—C18	1.325 (3)	C26—H26A	0.9800
O9—H9O	0.856 (10)	C26—H26B	0.9800
O10—C22	1.352 (3)	C26—H26C	0.9800
O10—H10O	0.850 (10)	C27—H27A	0.9800
O11—C25	1.239 (3)	C27—H27B	0.9800
O12—C28	1.226 (3)	C27—H27C	0.9800
N1—C25	1.312 (3)	C28—H28	0.9500
N1—C27	1.449 (3)	C29—H29A	0.9800
N1—C26	1.462 (4)	C29—H29B	0.9800
N2—C28	1.316 (3)	C29—H29C	0.9800
N2—C29	1.435 (5)	C30—H30A	0.9800
N2—C30	1.450 (4)	C30—H30B	0.9800
C1—C2	1.378 (4)	C30—H30C	0.9800
C1—C6	1.385 (3)	O13—C31	1.248 (8)
C2—C3	1.376 (4)	N3—C31	1.215 (9)
C2—H2	0.9500	N3—C33	1.495 (7)
C3—C4	1.401 (4)	N3—C32	1.502 (6)
C4—C5	1.367 (3)	C31—H31	0.9500
C4—H4	0.9500	C32—H32A	0.9800
C5—C6	1.399 (3)	C32—H32B	0.9800
C5—H5	0.9500	C32—H32C	0.9800
C6—C7	1.446 (3)	C33—H33A	0.9800
C7—C8	1.375 (3)	C33—H33B	0.9800
C8—C9	1.430 (3)	C33—H33C	0.9800
C8—C10	1.488 (3)	O13'—C31'	1.249 (8)
C10—C11	1.397 (3)	C31'—H31'	0.9500
C10—C15	1.402 (3)	C32'—H32D	0.9800
C11—C12	1.386 (3)	C32'—H32E	0.9800
C12—C13	1.380 (3)	C32'—H32F	0.9800
C12—H12	0.9500	C33'—H33D	0.9800
C13—C14	1.388 (3)	C33'—H33E	0.9800
C13—H13	0.9500	C33'—H33F	0.9800
C14—C15	1.397 (3)
C1—O1—C9	121.44 (19)	O9—C18—C16	124.8 (2)
C7—O3—H3O	120 (2)	O9—C18—C19	115.0 (2)
C3—O4—H4O	112 (2)	C16—C18—C19	120.2 (2)
C11—O5—H5O	111 (2)	C24—C19—C20	117.5 (2)
C14—O6—H6O	112 (2)	C24—C19—C18	118.5 (2)
C24—O7—C17	121.58 (18)	C20—C19—C18	123.9 (2)
C18—O9—H9O	115 (2)	C21—C20—C19	120.8 (2)
C22—O10—H10O	107 (3)	C21—C20—H20	119.6
C25—N1—C27	121.8 (2)	C19—C20—H20	119.6
C25—N1—C26	119.7 (2)	C20—C21—C22	119.9 (2)
C27—N1—C26	118.3 (2)	C20—C21—H21	120.1
C28—N2—C29	118.3 (3)	C22—C21—H21	120.1
C28—N2—C30	122.7 (3)	O10—C22—C23	116.8 (2)
C29—N2—C30	118.5 (3)	O10—C22—C21	122.7 (2)
O1—C1—C2	117.1 (2)	C23—C22—C21	120.5 (2)
O1—C1—C6	121.0 (2)	C24—C23—C22	118.5 (2)
C2—C1—C6	121.9 (2)	C24—C23—H23	120.7
C3—C2—C1	119.1 (2)	C22—C23—H23	120.7
C3—C2—H2	120.5	O7—C24—C23	116.3 (2)
C1—C2—H2	120.5	O7—C24—C19	120.9 (2)
O4—C3—C2	117.6 (2)	C23—C24—C19	122.7 (2)
O4—C3—C4	122.1 (2)	O11—C25—N1	124.1 (3)
C2—C3—C4	120.3 (2)	O11—C25—H25	118.0
C5—C4—C3	119.7 (2)	N1—C25—H25	118.0
C5—C4—H4	120.1	N1—C26—H26A	109.5
C3—C4—H4	120.1	N1—C26—H26B	109.5
C4—C5—C6	120.9 (2)	H26A—C26—H26B	109.5
C4—C5—H5	119.6	N1—C26—H26C	109.5
C6—C5—H5	119.6	H26A—C26—H26C	109.5
C1—C6—C5	118.1 (2)	H26B—C26—H26C	109.5
C1—C6—C7	118.5 (2)	N1—C27—H27A	109.5
C5—C6—C7	123.4 (2)	N1—C27—H27B	109.5
O3—C7—C8	125.5 (2)	H27A—C27—H27B	109.5
O3—C7—C6	114.5 (2)	N1—C27—H27C	109.5
C8—C7—C6	120.0 (2)	H27A—C27—H27C	109.5
C7—C8—C9	119.6 (2)	H27B—C27—H27C	109.5
C7—C8—C10	122.8 (2)	O12—C28—N2	124.7 (3)
C9—C8—C10	117.6 (2)	O12—C28—H28	117.6
O2—C9—O1	115.0 (2)	N2—C28—H28	117.6
O2—C9—C8	125.8 (2)	N2—C29—H29A	109.5
O1—C9—C8	119.2 (2)	N2—C29—H29B	109.5
C11—C10—C15	119.7 (2)	H29A—C29—H29B	109.5
C11—C10—C8	119.5 (2)	N2—C29—H29C	109.5
C15—C10—C8	120.8 (2)	H29A—C29—H29C	109.5
O5—C11—C12	122.8 (2)	H29B—C29—H29C	109.5
O5—C11—C10	117.2 (2)	N2—C30—H30A	109.5
C12—C11—C10	120.0 (2)	N2—C30—H30B	109.5
C13—C12—C11	120.1 (2)	H30A—C30—H30B	109.5
C13—C12—H12	119.9	N2—C30—H30C	109.5
C11—C12—H12	119.9	H30A—C30—H30C	109.5
C12—C13—C14	121.0 (2)	H30B—C30—H30C	109.5
C12—C13—H13	119.5	C31—N3—C33	124.7 (5)
C14—C13—H13	119.5	C31—N3—C32	128.3 (6)
O6—C14—C13	117.9 (2)	C33—N3—C32	107.0 (4)
O6—C14—C15	122.7 (2)	N3—C31—O13	124.1 (8)
C13—C14—C15	119.4 (2)	N3—C31—H31	117.9
C14—C15—C10	119.8 (2)	O13—C31—H31	117.9
C14—C15—C16	120.8 (2)	O13'—C31'—H31'	114.6
C10—C15—C16	119.4 (2)	H32D—C32'—H32E	109.5
C18—C16—C17	119.6 (2)	H32D—C32'—H32F	109.5
C18—C16—C15	123.4 (2)	H32E—C32'—H32F	109.5
C17—C16—C15	117.0 (2)	H33D—C33'—H33E	109.5
O8—C17—O7	115.0 (2)	H33D—C33'—H33F	109.5
O8—C17—C16	126.0 (2)	H33E—C33'—H33F	109.5
O7—C17—C16	119.01 (19)
C9—O1—C1—C2	174.0 (2)	C13—C14—C15—C16	−179.9 (2)
C9—O1—C1—C6	−6.0 (3)	C11—C10—C15—C14	1.7 (3)
O1—C1—C2—C3	−180.0 (2)	C8—C10—C15—C14	−179.5 (2)
C6—C1—C2—C3	0.0 (4)	C11—C10—C15—C16	−180.0 (2)
C1—C2—C3—O4	−179.2 (2)	C8—C10—C15—C16	−1.1 (3)
C1—C2—C3—C4	0.8 (4)	C14—C15—C16—C18	−71.0 (3)
O4—C3—C4—C5	178.9 (2)	C10—C15—C16—C18	110.7 (3)
C2—C3—C4—C5	−1.1 (4)	C14—C15—C16—C17	108.2 (3)
C3—C4—C5—C6	0.5 (4)	C10—C15—C16—C17	−70.2 (3)
O1—C1—C6—C5	179.4 (2)	C24—O7—C17—O8	−177.3 (2)
C2—C1—C6—C5	−0.6 (4)	C24—O7—C17—C16	3.1 (3)
O1—C1—C6—C7	2.0 (3)	C18—C16—C17—O8	179.7 (2)
C2—C1—C6—C7	−178.0 (2)	C15—C16—C17—O8	0.5 (3)
C4—C5—C6—C1	0.3 (3)	C18—C16—C17—O7	−0.9 (3)
C4—C5—C6—C7	177.6 (2)	C15—C16—C17—O7	180.0 (2)
C1—C6—C7—O3	−178.3 (2)	C17—C16—C18—O9	178.1 (2)
C5—C6—C7—O3	4.4 (3)	C15—C16—C18—O9	−2.7 (4)
C1—C6—C7—C8	2.8 (3)	C17—C16—C18—C19	−2.2 (3)
C5—C6—C7—C8	−174.5 (2)	C15—C16—C18—C19	176.9 (2)
O3—C7—C8—C9	177.7 (2)	O9—C18—C19—C24	−177.2 (2)
C6—C7—C8—C9	−3.6 (3)	C16—C18—C19—C24	3.1 (3)
O3—C7—C8—C10	−4.0 (4)	O9—C18—C19—C20	0.2 (3)
C6—C7—C8—C10	174.8 (2)	C16—C18—C19—C20	−179.5 (2)
C1—O1—C9—O2	−175.3 (2)	C24—C19—C20—C21	−1.0 (3)
C1—O1—C9—C8	5.1 (3)	C18—C19—C20—C21	−178.4 (2)
C7—C8—C9—O2	−179.9 (2)	C19—C20—C21—C22	1.0 (4)
C10—C8—C9—O2	1.7 (4)	C20—C21—C22—O10	179.4 (2)
C7—C8—C9—O1	−0.2 (3)	C20—C21—C22—C23	−0.2 (4)
C10—C8—C9—O1	−178.68 (19)	O10—C22—C23—C24	179.9 (3)
C7—C8—C10—C11	−68.2 (3)	C21—C22—C23—C24	−0.5 (4)
C9—C8—C10—C11	110.2 (2)	C17—O7—C24—C23	178.9 (2)
C7—C8—C10—C15	113.0 (3)	C17—O7—C24—C19	−2.2 (3)
C9—C8—C10—C15	−68.6 (3)	C22—C23—C24—O7	179.2 (2)
C15—C10—C11—O5	177.8 (2)	C22—C23—C24—C19	0.4 (4)
C8—C10—C11—O5	−1.0 (3)	C20—C19—C24—O7	−178.5 (2)
C15—C10—C11—C12	−1.1 (3)	C18—C19—C24—O7	−0.9 (3)
C8—C10—C11—C12	−179.9 (2)	C20—C19—C24—C23	0.3 (4)
O5—C11—C12—C13	−178.4 (2)	C18—C19—C24—C23	177.8 (2)
C10—C11—C12—C13	0.4 (3)	C27—N1—C25—O11	179.7 (2)
C11—C12—C13—C14	−0.4 (4)	C26—N1—C25—O11	4.5 (4)
C12—C13—C14—O6	−179.7 (2)	C29—N2—C28—O12	−2.8 (5)
C12—C13—C14—C15	1.0 (4)	C30—N2—C28—O12	−174.5 (3)
O6—C14—C15—C10	179.0 (2)	C33—N3—C31—O13	−0.6 (4)
C13—C14—C15—C10	−1.6 (3)	C32—N3—C31—O13	−178.9 (3)
O6—C14—C15—C16	0.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O12	0.86 (1)	1.72 (2)	2.540 (2)	161 (3)
O4—H4O···O11	0.85 (1)	1.79 (1)	2.638 (3)	172 (3)
O5—H5O···O8^i	0.85 (1)	1.88 (1)	2.718 (2)	170 (3)
O6—H6O···O13	0.85 (1)	2.04 (1)	2.883 (6)	172 (4)
O6—H6O···O13′	0.85 (1)	1.72 (2)	2.532 (5)	159 (4)
O9—H9O···O11^ii	0.86 (1)	1.84 (2)	2.642 (2)	156 (3)
O10—H10O···O2^iii	0.85 (1)	1.87 (2)	2.666 (2)	155 (4)

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1, −y+1, −z+1.