4,6,7-Trimethoxy­furo[2,3-b]quinoline-water (2/3)

The title compound, 2C₁₄H₁₃NO₄·3H₂O, was isolated from the plant Acronychia pendunculata. The asymmetric unit consists of two quinoline mol­ecules and three water mol­ecules of crystallization. Intra- and inter­molecular hydrogen bonds are highly effective in forming infinite chains parallel to the b axis, thereby stabilizing the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.102
• Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  O1     ..  C22     ..       2.87 Ang.

Alert level C
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack  -10.000
           From the CIF: _refine_ls_abs_structure_Flack_su   10.000
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ...      10.00
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......     -10.00
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.24

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           26.00
           From the CIF: _reflns_number_total               2897
           Count of symmetry unique reflns         2921
           Completeness (_total/calc)             99.18%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

4,6,7-Trimethoxyfuro[2,3-b]quinoline–water (2/3)

Crystal data

2C14H13NO4·3H2O	F(000) = 604
Mr = 572.56	Dx = 1.393 Mg m^−3
Monoclinic, P21	Melting point = 441.5–443.4 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 11.155 (2) Å	Cell parameters from 827 reflections
b = 7.0897 (16) Å	θ = 1.8–26.0°
c = 17.488 (4) Å	µ = 0.11 mm^−1
β = 99.313 (3)°	T = 298 K
V = 1364.9 (5) Å^3	Block, pale yellow
Z = 2	0.48 × 0.24 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2897 independent reflections
Radiation source: fine-focus sealed tube	2607 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 83.66 pixels mm^-1	θmax = 26.0°, θmin = 1.8°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→8
Tmin = 0.949, Tmax = 0.982	l = −21→19
7393 measured reflections

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0543P)^2 + 0.0928P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max < 0.001
2897 reflections	Δρmax = 0.15 e Å^−3
400 parameters	Δρmin = −0.13 e Å^−3
1 restraint	Absolute structure: (Flack, 1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −10 (10)

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.

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

	x	y	z	Uiso*/Ueq
O1	0.55065 (18)	0.0311 (4)	0.86334 (13)	0.0625 (6)
O2	0.23178 (18)	0.1488 (4)	0.65630 (10)	0.0572 (6)
O3	−0.12262 (17)	0.2585 (3)	0.79190 (11)	0.0557 (6)
O4	−0.04274 (18)	0.2326 (4)	0.93910 (11)	0.0607 (6)
O5	0.39668 (18)	0.0215 (4)	0.22472 (12)	0.0603 (6)
O6	0.73055 (17)	0.1253 (4)	0.09569 (10)	0.0559 (6)
O7	1.07008 (17)	0.2434 (4)	0.31129 (11)	0.0562 (6)
O8	0.98244 (18)	0.2238 (4)	0.43809 (11)	0.0615 (6)
N9	0.3615 (2)	0.0904 (4)	0.89482 (13)	0.0502 (6)
N21	0.58174 (19)	0.0843 (4)	0.30025 (13)	0.0477 (6)
C2	0.5979 (3)	0.0250 (6)	0.7958 (2)	0.0671 (10)
H2	0.6795	0.0015	0.7941	0.081*
C3	0.5168 (3)	0.0558 (5)	0.7335 (2)	0.0619 (9)
H3	0.5304	0.0566	0.6824	0.074*
C4	0.2823 (2)	0.1278 (4)	0.73091 (15)	0.0433 (6)
C5	0.0760 (2)	0.1922 (4)	0.75961 (15)	0.0434 (6)
H5	0.0469	0.2031	0.7069	0.052*
C6	−0.0017 (2)	0.2167 (4)	0.81136 (15)	0.0438 (6)
C7	0.0425 (2)	0.2018 (4)	0.89214 (15)	0.0460 (7)
C8	0.1614 (3)	0.1592 (5)	0.91736 (15)	0.0485 (7)
H8	0.1890	0.1479	0.9703	0.058*
C10	0.3078 (3)	0.1384 (6)	0.59773 (17)	0.0710 (10)
H10A	0.3721	0.2294	0.6086	0.107*
H10B	0.2603	0.1647	0.5480	0.107*
H10C	0.3420	0.0142	0.5974	0.107*
C11	−0.1705 (3)	0.2678 (6)	0.71123 (18)	0.0603 (8)
H11A	−0.1280	0.3630	0.6872	0.090*
H11B	−0.2553	0.2988	0.7046	0.090*
H11C	−0.1603	0.1479	0.6876	0.090*
C12	−0.0006 (3)	0.2293 (6)	1.02102 (16)	0.0660 (9)
H12A	0.0305	0.1062	1.0360	0.099*
H12B	−0.0668	0.2583	1.0480	0.099*
H12C	0.0626	0.3212	1.0339	0.099*
C14	0.3556 (3)	0.0058 (6)	0.14601 (18)	0.0628 (9)
H14	0.2757	−0.0231	0.1251	0.075*
C15	0.4416 (3)	0.0359 (5)	0.10377 (18)	0.0547 (8)
H15	0.4328	0.0342	0.0500	0.066*
C16	0.6742 (2)	0.1115 (4)	0.15748 (15)	0.0431 (6)
C17	0.8754 (2)	0.1786 (4)	0.23381 (15)	0.0439 (6)
H17	0.9080	0.1882	0.1883	0.053*
C18	0.9483 (2)	0.2040 (4)	0.30248 (16)	0.0443 (6)
C19	0.8998 (2)	0.1920 (4)	0.37283 (15)	0.0470 (7)
C20	0.7799 (2)	0.1509 (5)	0.37083 (16)	0.0480 (7)
H20	0.7491	0.1410	0.4170	0.058*
C22	0.6627 (3)	0.0945 (7)	0.02065 (15)	0.0677 (10)
H22A	0.6290	−0.0304	0.0179	0.102*
H22B	0.7152	0.1076	−0.0175	0.102*
H22C	0.5983	0.1853	0.0108	0.102*
C23	1.1237 (3)	0.2481 (5)	0.24314 (18)	0.0588 (8)
H23A	1.1053	0.1332	0.2146	0.088*
H23B	1.2101	0.2610	0.2570	0.088*
H23C	1.0919	0.3533	0.2117	0.088*
C24	0.9404 (3)	0.2205 (8)	0.51069 (17)	0.0757 (11)
H24A	0.8771	0.3124	0.5104	0.114*
H24B	1.0064	0.2496	0.5514	0.114*
H24C	0.9093	0.0974	0.5192	0.114*
C3A	0.4016 (2)	0.0882 (4)	0.76031 (15)	0.0472 (7)
C4A	0.2001 (2)	0.1506 (4)	0.78464 (14)	0.0391 (6)
C8A	0.2438 (2)	0.1319 (4)	0.86490 (14)	0.0430 (6)
C9A	0.4302 (2)	0.0716 (4)	0.84173 (17)	0.0486 (7)
C15A	0.5526 (2)	0.0725 (4)	0.15760 (16)	0.0463 (7)
C16A	0.7507 (2)	0.1378 (4)	0.22970 (15)	0.0407 (6)
C20A	0.7019 (2)	0.1232 (4)	0.29958 (15)	0.0430 (6)
C21A	0.5179 (2)	0.0625 (4)	0.23160 (16)	0.0477 (7)
O9	0.4384 (2)	0.0839 (5)	0.42135 (15)	0.0666 (6)
H9A	0.420 (4)	−0.042 (7)	0.431 (2)	0.081 (13)*
H9B	0.474 (3)	0.083 (7)	0.385 (2)	0.079 (12)*
O10	0.6119 (3)	0.2163 (5)	0.54354 (19)	0.0857 (9)
H10D	0.651 (4)	0.122 (7)	0.555 (2)	0.074 (14)*
H10E	0.555 (4)	0.190 (9)	0.507 (3)	0.105 (17)*
O11	0.2703 (3)	0.3743 (5)	0.42177 (18)	0.0842 (9)
H11D	0.321 (4)	0.280 (7)	0.420 (2)	0.084 (14)*
H11E	0.200 (4)	0.329 (8)	0.407 (3)	0.110 (17)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0447 (11)	0.0709 (16)	0.0715 (14)	0.0036 (11)	0.0076 (10)	−0.0052 (12)
O2	0.0572 (12)	0.0751 (16)	0.0425 (10)	−0.0016 (11)	0.0180 (8)	−0.0001 (11)
O3	0.0459 (11)	0.0682 (15)	0.0542 (11)	0.0068 (10)	0.0119 (8)	−0.0041 (11)
O4	0.0560 (12)	0.0782 (16)	0.0529 (11)	0.0005 (12)	0.0234 (9)	−0.0065 (12)
O5	0.0399 (10)	0.0764 (16)	0.0663 (13)	−0.0083 (10)	0.0134 (9)	−0.0007 (12)
O6	0.0509 (11)	0.0756 (16)	0.0440 (10)	−0.0041 (11)	0.0159 (8)	0.0018 (11)
O7	0.0396 (10)	0.0742 (15)	0.0570 (11)	−0.0058 (10)	0.0145 (8)	−0.0025 (12)
O8	0.0494 (11)	0.0866 (17)	0.0487 (11)	−0.0086 (12)	0.0091 (9)	−0.0026 (12)
N9	0.0471 (13)	0.0563 (16)	0.0472 (12)	−0.0013 (12)	0.0078 (10)	0.0014 (12)
N21	0.0431 (12)	0.0517 (15)	0.0512 (13)	−0.0016 (11)	0.0164 (10)	0.0032 (12)
C2	0.0449 (17)	0.082 (3)	0.079 (2)	0.0014 (17)	0.0236 (17)	−0.011 (2)
C3	0.0533 (17)	0.069 (2)	0.069 (2)	−0.0060 (16)	0.0277 (16)	−0.0121 (18)
C4	0.0483 (15)	0.0406 (16)	0.0427 (13)	−0.0064 (12)	0.0125 (11)	−0.0024 (12)
C5	0.0472 (14)	0.0417 (16)	0.0416 (13)	−0.0022 (13)	0.0084 (11)	−0.0015 (12)
C6	0.0449 (14)	0.0379 (15)	0.0501 (14)	−0.0034 (12)	0.0122 (11)	−0.0027 (13)
C7	0.0505 (15)	0.0427 (17)	0.0487 (15)	−0.0037 (13)	0.0195 (12)	−0.0035 (13)
C8	0.0542 (16)	0.0543 (18)	0.0391 (13)	−0.0045 (14)	0.0137 (11)	0.0013 (13)
C10	0.079 (2)	0.093 (3)	0.0469 (16)	−0.007 (2)	0.0284 (15)	−0.0027 (19)
C11	0.0465 (15)	0.069 (2)	0.0634 (18)	0.0044 (15)	0.0033 (13)	−0.0043 (17)
C12	0.075 (2)	0.075 (3)	0.0547 (19)	0.0027 (19)	0.0294 (16)	−0.0044 (18)
C14	0.0447 (16)	0.075 (2)	0.067 (2)	−0.0079 (16)	0.0035 (14)	−0.0051 (18)
C15	0.0495 (16)	0.058 (2)	0.0560 (17)	−0.0017 (15)	0.0068 (13)	−0.0018 (16)
C16	0.0455 (14)	0.0378 (16)	0.0481 (14)	0.0020 (12)	0.0137 (11)	0.0042 (12)
C17	0.0444 (14)	0.0441 (16)	0.0471 (14)	0.0007 (12)	0.0193 (11)	0.0016 (12)
C18	0.0382 (13)	0.0413 (16)	0.0556 (15)	0.0000 (12)	0.0136 (11)	−0.0004 (13)
C19	0.0501 (15)	0.0436 (17)	0.0482 (15)	−0.0002 (13)	0.0108 (12)	0.0014 (13)
C20	0.0499 (15)	0.0514 (18)	0.0465 (14)	−0.0009 (13)	0.0188 (12)	0.0023 (13)
C22	0.0584 (18)	0.102 (3)	0.0432 (15)	0.002 (2)	0.0099 (13)	0.0094 (19)
C23	0.0426 (15)	0.067 (2)	0.0703 (19)	−0.0014 (15)	0.0214 (13)	0.0023 (18)
C24	0.066 (2)	0.112 (3)	0.0491 (16)	−0.007 (2)	0.0083 (14)	−0.002 (2)
C3A	0.0495 (15)	0.0430 (16)	0.0524 (15)	−0.0065 (13)	0.0185 (12)	−0.0054 (13)
C4A	0.0436 (13)	0.0321 (14)	0.0429 (13)	−0.0050 (11)	0.0110 (11)	−0.0019 (11)
C8A	0.0457 (14)	0.0387 (16)	0.0460 (14)	−0.0053 (12)	0.0114 (11)	−0.0013 (13)
C9A	0.0410 (14)	0.0468 (18)	0.0576 (16)	−0.0033 (13)	0.0071 (12)	−0.0037 (14)
C15A	0.0458 (14)	0.0414 (17)	0.0525 (15)	0.0001 (13)	0.0104 (12)	0.0002 (13)
C16A	0.0416 (13)	0.0341 (14)	0.0483 (14)	0.0012 (11)	0.0131 (11)	0.0021 (12)
C20A	0.0417 (14)	0.0396 (16)	0.0501 (14)	0.0007 (12)	0.0146 (11)	0.0010 (13)
C21A	0.0412 (14)	0.0449 (17)	0.0592 (17)	−0.0008 (13)	0.0150 (13)	0.0039 (14)
O9	0.0678 (15)	0.076 (2)	0.0604 (14)	0.0032 (13)	0.0250 (11)	−0.0016 (14)
O10	0.084 (2)	0.082 (2)	0.086 (2)	0.0151 (19)	−0.0022 (16)	−0.0185 (18)
O11	0.0682 (18)	0.071 (2)	0.104 (2)	0.0030 (15)	−0.0155 (16)	−0.0044 (16)

Geometric parameters (Å, º)

O1—C9A	1.366 (3)	C11—H11B	0.9600
O1—C2	1.371 (4)	C11—H11C	0.9600
O2—C4	1.343 (3)	C12—H12A	0.9600
O2—C10	1.434 (3)	C12—H12B	0.9600
O3—C6	1.369 (3)	C12—H12C	0.9600
O3—C11	1.427 (4)	C14—C15	1.319 (4)
O4—C7	1.371 (3)	C14—H14	0.9300
O4—C12	1.434 (4)	C15—C15A	1.452 (4)
O5—C21A	1.369 (3)	C15—H15	0.9300
O5—C14	1.383 (4)	C16—C15A	1.385 (4)
O6—C16	1.339 (3)	C16—C16A	1.417 (4)
O6—C22	1.421 (3)	C17—C18	1.349 (4)
O7—C18	1.371 (3)	C17—C16A	1.412 (3)
O7—C23	1.418 (3)	C17—H17	0.9300
O8—C19	1.365 (3)	C18—C19	1.425 (4)
O8—C24	1.423 (3)	C19—C20	1.363 (4)
N9—C9A	1.303 (3)	C20—C20A	1.413 (4)
N9—C8A	1.365 (3)	C20—H20	0.9300
N21—C21A	1.302 (4)	C22—H22A	0.9600
N21—C20A	1.371 (3)	C22—H22B	0.9600
C2—C3	1.316 (5)	C22—H22C	0.9600
C2—H2	0.9300	C23—H23A	0.9600
C3—C3A	1.456 (4)	C23—H23B	0.9600
C3—H3	0.9300	C23—H23C	0.9600
C4—C3A	1.376 (4)	C24—H24A	0.9600
C4—C4A	1.424 (3)	C24—H24B	0.9600
C5—C6	1.362 (3)	C24—H24C	0.9600
C5—C4A	1.414 (4)	C3A—C9A	1.413 (4)
C5—H5	0.9300	C4A—C8A	1.415 (3)
C6—C7	1.423 (4)	C15A—C21A	1.412 (4)
C7—C8	1.363 (4)	C16A—C20A	1.419 (3)
C8—C8A	1.413 (4)	O9—H9A	0.93 (5)
C8—H8	0.9300	O9—H9B	0.80 (4)
C10—H10A	0.9600	O10—H10D	0.80 (5)
C10—H10B	0.9600	O10—H10E	0.85 (4)
C10—H10C	0.9600	O11—H11D	0.88 (5)
C11—H11A	0.9600	O11—H11E	0.85 (5)
C9A—O1—C2	105.5 (2)	C18—C17—C16A	121.3 (2)
C4—O2—C10	119.0 (2)	C18—C17—H17	119.3
C6—O3—C11	116.9 (2)	C16A—C17—H17	119.3
C7—O4—C12	116.7 (2)	C17—C18—O7	124.8 (2)
C21A—O5—C14	105.6 (2)	C17—C18—C19	120.1 (2)
C16—O6—C22	119.0 (2)	O7—C18—C19	115.0 (2)
C18—O7—C23	117.1 (2)	C20—C19—O8	125.7 (2)
C19—O8—C24	117.9 (2)	C20—C19—C18	119.9 (2)
C9A—N9—C8A	112.9 (2)	O8—C19—C18	114.4 (2)
C21A—N21—C20A	114.0 (2)	C19—C20—C20A	120.9 (2)
C3—C2—O1	113.5 (3)	C19—C20—H20	119.5
C3—C2—H2	123.3	C20A—C20—H20	119.6
O1—C2—H2	123.3	O6—C22—H22A	109.5
C2—C3—C3A	106.5 (3)	O6—C22—H22B	109.5
C2—C3—H3	126.7	H22A—C22—H22B	109.5
C3A—C3—H3	126.7	O6—C22—H22C	109.5
O2—C4—C3A	127.9 (2)	H22A—C22—H22C	109.5
O2—C4—C4A	114.5 (2)	H22B—C22—H22C	109.5
C3A—C4—C4A	117.6 (2)	O7—C23—H23A	109.5
C6—C5—C4A	121.2 (2)	O7—C23—H23B	109.5
C6—C5—H5	119.4	H23A—C23—H23B	109.5
C4A—C5—H5	119.4	O7—C23—H23C	109.5
C5—C6—O3	124.7 (2)	H23A—C23—H23C	109.5
C5—C6—C7	119.7 (2)	H23B—C23—H23C	109.5
O3—C6—C7	115.6 (2)	O8—C24—H24A	109.5
C8—C7—O4	125.1 (2)	O8—C24—H24B	109.5
C8—C7—C6	120.0 (2)	H24A—C24—H24B	109.5
O4—C7—C6	114.9 (2)	O8—C24—H24C	109.5
C7—C8—C8A	121.4 (2)	H24A—C24—H24C	109.5
C7—C8—H8	119.3	H24B—C24—H24C	109.5
C8A—C8—H8	119.3	C4—C3A—C9A	116.2 (2)
O2—C10—H10A	109.5	C4—C3A—C3	139.7 (3)
O2—C10—H10B	109.5	C9A—C3A—C3	104.1 (3)
H10A—C10—H10B	109.5	C5—C4A—C8A	119.3 (2)
O2—C10—H10C	109.5	C5—C4A—C4	121.5 (2)
H10A—C10—H10C	109.5	C8A—C4A—C4	119.2 (2)
H10B—C10—H10C	109.5	N9—C8A—C8	117.8 (2)
O3—C11—H11A	109.5	N9—C8A—C4A	123.8 (2)
O3—C11—H11B	109.5	C8—C8A—C4A	118.4 (2)
H11A—C11—H11B	109.5	N9—C9A—O1	119.4 (3)
O3—C11—H11C	109.5	N9—C9A—C3A	130.3 (3)
H11A—C11—H11C	109.5	O1—C9A—C3A	110.4 (2)
H11B—C11—H11C	109.5	C16—C15A—C21A	115.2 (2)
O4—C12—H12A	109.5	C16—C15A—C15	140.1 (3)
O4—C12—H12B	109.5	C21A—C15A—C15	104.7 (2)
H12A—C12—H12B	109.5	C17—C16A—C16	121.2 (2)
O4—C12—H12C	109.5	C17—C16A—C20A	118.9 (2)
H12A—C12—H12C	109.5	C16—C16A—C20A	119.9 (2)
H12B—C12—H12C	109.5	N21—C20A—C20	118.9 (2)
C15—C14—O5	113.0 (3)	N21—C20A—C16A	122.2 (2)
C15—C14—H14	123.5	C20—C20A—C16A	118.8 (2)
O5—C14—H14	123.5	N21—C21A—O5	119.4 (2)
C14—C15—C15A	106.7 (3)	N21—C21A—C15A	130.5 (2)
C14—C15—H15	126.7	O5—C21A—C15A	110.1 (2)
C15A—C15—H15	126.7	H9A—O9—H9B	107 (4)
O6—C16—C15A	127.1 (2)	H10D—O10—H10E	108 (5)
O6—C16—C16A	114.6 (2)	H11D—O11—H11E	106 (4)
C15A—C16—C16A	118.3 (2)
C9A—O1—C2—C3	−0.9 (4)	C9A—N9—C8A—C8	−178.7 (3)
O1—C2—C3—C3A	0.6 (4)	C9A—N9—C8A—C4A	0.7 (4)
C10—O2—C4—C3A	−3.0 (5)	C7—C8—C8A—N9	179.8 (3)
C10—O2—C4—C4A	176.8 (3)	C7—C8—C8A—C4A	0.2 (4)
C4A—C5—C6—O3	179.6 (3)	C5—C4A—C8A—N9	179.4 (3)
C4A—C5—C6—C7	0.5 (4)	C4—C4A—C8A—N9	−0.9 (4)
C11—O3—C6—C5	3.1 (4)	C5—C4A—C8A—C8	−1.1 (4)
C11—O3—C6—C7	−177.9 (3)	C4—C4A—C8A—C8	178.6 (3)
C12—O4—C7—C8	3.5 (5)	C8A—N9—C9A—O1	179.6 (3)
C12—O4—C7—C6	−176.6 (3)	C8A—N9—C9A—C3A	0.2 (5)
C5—C6—C7—C8	−1.4 (4)	C2—O1—C9A—N9	−178.6 (3)
O3—C6—C7—C8	179.5 (3)	C2—O1—C9A—C3A	0.9 (4)
C5—C6—C7—O4	178.8 (3)	C4—C3A—C9A—N9	−1.0 (5)
O3—C6—C7—O4	−0.4 (4)	C3—C3A—C9A—N9	178.8 (3)
O4—C7—C8—C8A	−179.2 (3)	C4—C3A—C9A—O1	179.6 (3)
C6—C7—C8—C8A	1.0 (4)	C3—C3A—C9A—O1	−0.6 (3)
C21A—O5—C14—C15	−0.7 (4)	O6—C16—C15A—C21A	178.8 (3)
O5—C14—C15—C15A	1.1 (4)	C16A—C16—C15A—C21A	−0.1 (4)
C22—O6—C16—C15A	−1.2 (5)	O6—C16—C15A—C15	−1.3 (6)
C22—O6—C16—C16A	177.7 (3)	C16A—C16—C15A—C15	179.8 (4)
C16A—C17—C18—O7	179.8 (3)	C14—C15—C15A—C16	179.0 (4)
C16A—C17—C18—C19	−0.7 (4)	C14—C15—C15A—C21A	−1.0 (4)
C23—O7—C18—C17	−3.3 (4)	C18—C17—C16A—C16	179.9 (3)
C23—O7—C18—C19	177.1 (3)	C18—C17—C16A—C20A	−0.1 (4)
C24—O8—C19—C20	−2.3 (5)	O6—C16—C16A—C17	1.2 (4)
C24—O8—C19—C18	178.0 (3)	C15A—C16—C16A—C17	−179.8 (3)
C17—C18—C19—C20	1.3 (4)	O6—C16—C16A—C20A	−178.9 (2)
O7—C18—C19—C20	−179.1 (3)	C15A—C16—C16A—C20A	0.2 (4)
C17—C18—C19—O8	−178.9 (3)	C21A—N21—C20A—C20	179.6 (3)
O7—C18—C19—O8	0.7 (4)	C21A—N21—C20A—C16A	−0.1 (4)
O8—C19—C20—C20A	179.1 (3)	C19—C20—C20A—N21	−179.3 (3)
C18—C19—C20—C20A	−1.2 (4)	C19—C20—C20A—C16A	0.4 (4)
O2—C4—C3A—C9A	−179.4 (3)	C17—C16A—C20A—N21	179.9 (3)
C4A—C4—C3A—C9A	0.8 (4)	C16—C16A—C20A—N21	−0.1 (4)
O2—C4—C3A—C3	0.9 (7)	C17—C16A—C20A—C20	0.3 (4)
C4A—C4—C3A—C3	−179.0 (4)	C16—C16A—C20A—C20	−179.7 (3)
C2—C3—C3A—C4	179.8 (4)	C20A—N21—C21A—O5	179.5 (3)
C2—C3—C3A—C9A	0.0 (4)	C20A—N21—C21A—C15A	0.1 (5)
C6—C5—C4A—C8A	0.7 (4)	C14—O5—C21A—N21	−179.5 (3)
C6—C5—C4A—C4	−179.0 (3)	C14—O5—C21A—C15A	0.0 (3)
O2—C4—C4A—C5	−0.1 (4)	C16—C15A—C21A—N21	0.0 (5)
C3A—C4—C4A—C5	179.7 (3)	C15—C15A—C21A—N21	−180.0 (3)
O2—C4—C4A—C8A	−179.8 (3)	C16—C15A—C21A—O5	−179.4 (3)
C3A—C4—C4A—C8A	0.0 (4)	C15—C15A—C21A—O5	0.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2	0.93	2.40	2.719 (3)	100
C17—H17···O6	0.93	2.39	2.706 (3)	100
O9—H9A···O10^i	0.94 (5)	1.82 (5)	2.756 (5)	176 (3)
O9—H9B···N21	0.80 (3)	2.05 (3)	2.853 (3)	174 (4)
O10—H10D···O11^i	0.81 (5)	1.98 (5)	2.778 (5)	173 (5)
O10—H10E···O9	0.85 (5)	1.97 (5)	2.803 (4)	169 (6)
O11—H11D···O9	0.88 (5)	1.91 (5)	2.786 (5)	176 (3)
O11—H11E···O7^ii	0.85 (5)	2.12 (5)	2.861 (4)	146 (5)

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