Brucinium 2-carb­oxy-6-nitro­phthalate dihydrate: the 1:1 proton-transfer compound of brucine with 3-nitro­phthalic acid

In the title compound (systematic name: 2,3-dimeth­oxy-10-oxostrychnidinium 2-carb­oxy-6-nitro­phthalate dihydrate), C₂₃H₂₇N₂O₄⁺·C₈H₄NO₆⁻·2H₂O, the carboxylic acid and carboxyl­ate groups of the hydrogenphthalate anions form head-to-tail catemeric chains of strong inter­molecular O—H...O hydrogen bonds [O...O distance = 2.563 (5) Å] along the 2₁ screw axes parallel to the a axis. The chains further associate with the water mol­ecules, forming sheet structures parallel to (010). The protonated N atom at the 19-position of the brucine mol­ecule forms a peripheral inter­molecular hydrogen bond with the carboxyl­ate group of the anion.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.065
• wR factor = 0.179
• Data-to-parameter ratio = 9.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C23
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.35
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O11P   -   H11P   ...       1.01 Ang.
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O1W    -   H12W   ...       1.01 Ang.

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           27.73
           From the CIF: _reflns_number_total               3974
           Count of symmetry unique reflns         3974
           Completeness (_total/calc)            100.00%
           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
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

2,3-dimethoxystrychnidinium-10-one 2-carboxy-6-nitrophthalate dihydrate

Crystal data

C23H27N2O4^+·C8H4NO6^−·2H2O	Dx = 1.435 Mg m^−3
Mr = 641.62	Melting point = 471.0–474.4 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P2ac 2ab	Cell parameters from 25 reflections
a = 12.7001 (14) Å	θ = 12.7–17.2°
b = 32.015 (5) Å	µ = 0.11 mm^−1
c = 7.3041 (19) Å	T = 297 K
V = 2969.8 (10) Å^3	Prism, orange–yellow
Z = 4	0.40 × 0.35 × 0.35 mm
F(000) = 1352

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.028
Radiation source: Rigaku rotating anode	θmax = 27.7°, θmin = 2.5°
Graphite monochromator	h = −7→16
ω–2θ scans	k = −41→18
5089 measured reflections	l = −4→9
3974 independent reflections	3 standard reflections every 150 min
2953 reflections with F^2 > 2σ(F)^2	intensity decay: 2.1%

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)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.179	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.4458P] where P = (Fo^2 + 2Fc^2)/3
S = 1.17	(Δ/σ)max = 0.002
3974 reflections	Δρmax = 0.42 e Å^−3
424 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0072 (15)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O21	0.6655 (2)	0.38581 (9)	0.6358 (6)	0.0581 (12)
O24	−0.0224 (2)	0.46150 (10)	0.6768 (5)	0.0574 (10)
O25	0.3019 (2)	0.53119 (9)	0.6290 (4)	0.0504 (9)
O31	0.6614 (2)	0.46483 (10)	0.5884 (6)	0.0657 (12)
N9	0.2780 (2)	0.46301 (10)	0.7060 (4)	0.0374 (9)
N19	0.1573 (3)	0.32646 (11)	0.7461 (5)	0.0424 (10)
C1	0.4752 (3)	0.38188 (13)	0.6829 (6)	0.0435 (13)
C2	0.5671 (3)	0.40331 (13)	0.6512 (7)	0.0449 (13)
C3	0.5657 (3)	0.44730 (13)	0.6291 (7)	0.0450 (13)
C4	0.4732 (3)	0.46973 (13)	0.6447 (6)	0.0423 (11)
C5	0.3808 (3)	0.44698 (12)	0.6822 (6)	0.0384 (11)
C6	0.3813 (3)	0.40413 (12)	0.6975 (6)	0.0377 (11)
C7	0.2720 (3)	0.38780 (12)	0.7409 (5)	0.0362 (11)
C8	0.2022 (3)	0.42771 (12)	0.7137 (5)	0.0348 (10)
C10	0.2431 (4)	0.50144 (13)	0.6576 (6)	0.0412 (11)
C11	0.1249 (3)	0.50543 (14)	0.6454 (7)	0.0487 (14)
C12	0.0656 (3)	0.46835 (14)	0.5601 (6)	0.0497 (14)
C13	0.1393 (3)	0.43117 (13)	0.5372 (6)	0.0411 (11)
C14	0.0946 (3)	0.38906 (14)	0.4714 (6)	0.0467 (14)
C15	0.1886 (4)	0.36032 (14)	0.4419 (6)	0.0483 (14)
C16	0.2368 (3)	0.35014 (12)	0.6252 (6)	0.0405 (11)
C17	0.2632 (3)	0.37045 (12)	0.9358 (6)	0.0414 (11)
C18	0.1617 (3)	0.34605 (13)	0.9339 (6)	0.0453 (12)
C20	0.0467 (3)	0.32614 (15)	0.6693 (7)	0.0497 (16)
C21	0.0175 (3)	0.36902 (13)	0.6057 (7)	0.0477 (14)
C22	−0.0678 (4)	0.38784 (15)	0.6642 (7)	0.0543 (16)
C23	−0.0976 (4)	0.43156 (18)	0.6111 (10)	0.072 (2)
C211	0.6684 (3)	0.34136 (14)	0.6379 (7)	0.0527 (14)
C311	0.6643 (4)	0.50830 (16)	0.5620 (11)	0.078 (2)
O11P	0.4167 (2)	0.28992 (11)	0.1063 (6)	0.0643 (13)
O12P	0.5554 (2)	0.24858 (10)	0.0583 (6)	0.0646 (13)
O21P	0.7565 (2)	0.25080 (9)	0.2464 (5)	0.0573 (10)
O22P	0.7889 (3)	0.27031 (11)	−0.0427 (5)	0.0617 (11)
O31P	0.9101 (3)	0.32260 (13)	0.2268 (7)	0.0879 (16)
O32P	0.9105 (3)	0.38559 (12)	0.1284 (6)	0.0759 (15)
N31P	0.8653 (3)	0.35343 (14)	0.1759 (6)	0.0550 (13)
C1P	0.5835 (3)	0.31965 (13)	0.1418 (6)	0.0404 (11)
C2P	0.6941 (3)	0.31643 (13)	0.1438 (6)	0.0401 (11)
C3P	0.7487 (3)	0.35352 (14)	0.1702 (6)	0.0445 (11)
C4P	0.7009 (4)	0.39179 (14)	0.1968 (8)	0.0573 (16)
C5P	0.5930 (4)	0.39382 (15)	0.1970 (8)	0.0607 (16)
C6P	0.5350 (3)	0.35814 (15)	0.1703 (7)	0.0529 (15)
C11P	0.5176 (3)	0.28200 (13)	0.0976 (6)	0.0445 (13)
C21P	0.7506 (3)	0.27520 (13)	0.1147 (7)	0.0448 (13)
O1W	0.4598 (3)	0.27687 (14)	0.6112 (9)	0.110 (2)
O2W	0.6736 (4)	0.24351 (13)	0.6213 (6)	0.0877 (17)
H1	0.476000	0.351800	0.695100	0.0530*
H4	0.472600	0.499100	0.628900	0.0530*
H8	0.155900	0.431000	0.815800	0.0420*
H11A	0.107700	0.530000	0.579000	0.0590*
H11B	0.098400	0.509000	0.769600	0.0590*
H12	0.040400	0.476400	0.442700	0.0590*
H13	0.189700	0.439400	0.445900	0.0500*
H14	0.060000	0.393700	0.356400	0.0570*
H15A	0.166400	0.335100	0.381700	0.0610*
H15B	0.240400	0.373500	0.364900	0.0610*
H16	0.297100	0.332200	0.605300	0.0490*
H17A	0.259700	0.392300	1.025400	0.0500*
H17B	0.320600	0.352500	0.966000	0.0500*
H18A	0.161200	0.325300	1.027200	0.0560*
H18B	0.103000	0.364200	0.951600	0.0560*
H19	0.189 (4)	0.2994 (14)	0.757 (6)	0.054 (13)*
H20A	0.043200	0.307300	0.566800	0.0600*
H20B	−0.002000	0.316800	0.759700	0.0600*
H21A	0.671100	0.331500	0.760300	0.0630*
H21B	0.730300	0.331500	0.574500	0.0630*
H21C	0.608300	0.330000	0.578300	0.0630*
H22	−0.113100	0.373700	0.752500	0.0670*
H23A	−0.100600	0.432800	0.479000	0.0860*
H23B	−0.166600	0.438200	0.656200	0.0860*
H31A	0.661800	0.523100	0.674500	0.0900*
H31B	0.602500	0.516800	0.491000	0.0900*
H31C	0.724600	0.516500	0.494600	0.0900*
H4P	0.742600	0.416000	0.214500	0.0690*
H5P	0.558900	0.419800	0.220300	0.0730*
H6P	0.460300	0.359600	0.170900	0.0630*
H11P	0.374 (7)	0.264 (3)	0.080 (12)	0.16 (3)*
H11W	0.512500	0.255900	0.614000	0.0450*
H12W	0.403700	0.264400	0.693300	0.0450*
H21W	0.708600	0.252900	0.725000	0.0450*
H22W	0.700000	0.243200	0.508000	0.0450*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O21	0.0277 (13)	0.0426 (16)	0.104 (3)	0.0039 (12)	0.0008 (17)	0.0032 (18)
O24	0.0303 (14)	0.0590 (19)	0.083 (2)	0.0060 (14)	0.0015 (16)	−0.0018 (18)
O25	0.0484 (16)	0.0401 (15)	0.0628 (18)	−0.0029 (14)	−0.0077 (16)	0.0021 (14)
O31	0.0298 (13)	0.0503 (17)	0.117 (3)	−0.0079 (13)	0.0044 (19)	0.004 (2)
N9	0.0288 (14)	0.0371 (16)	0.0462 (18)	0.0012 (13)	−0.0007 (14)	0.0025 (14)
N19	0.0320 (16)	0.0426 (19)	0.0525 (19)	−0.0014 (15)	0.0005 (16)	0.0019 (16)
C1	0.0326 (18)	0.041 (2)	0.057 (3)	0.0024 (16)	−0.0025 (18)	0.0023 (19)
C2	0.0266 (16)	0.046 (2)	0.062 (3)	0.0031 (16)	−0.0005 (19)	−0.001 (2)
C3	0.0281 (17)	0.045 (2)	0.062 (3)	−0.0052 (16)	−0.001 (2)	−0.001 (2)
C4	0.0319 (18)	0.041 (2)	0.054 (2)	−0.0016 (16)	−0.0027 (19)	0.0007 (19)
C5	0.0292 (17)	0.040 (2)	0.046 (2)	0.0014 (15)	−0.0036 (17)	−0.0012 (17)
C6	0.0280 (17)	0.040 (2)	0.045 (2)	−0.0007 (15)	−0.0028 (16)	0.0002 (17)
C7	0.0269 (16)	0.0377 (19)	0.044 (2)	0.0012 (15)	−0.0033 (15)	−0.0001 (17)
C8	0.0266 (15)	0.0385 (18)	0.0392 (19)	−0.0003 (15)	0.0014 (16)	0.0013 (16)
C10	0.0377 (18)	0.0409 (19)	0.045 (2)	0.0011 (16)	−0.0019 (18)	−0.0001 (18)
C11	0.0352 (19)	0.047 (2)	0.064 (3)	0.0084 (18)	−0.001 (2)	0.006 (2)
C12	0.039 (2)	0.051 (2)	0.059 (3)	0.0076 (19)	−0.010 (2)	0.008 (2)
C13	0.0374 (19)	0.046 (2)	0.040 (2)	0.0003 (18)	−0.0040 (18)	0.0030 (17)
C14	0.042 (2)	0.059 (3)	0.039 (2)	−0.002 (2)	−0.0095 (18)	0.001 (2)
C15	0.046 (2)	0.055 (3)	0.044 (2)	−0.006 (2)	−0.0004 (19)	−0.005 (2)
C16	0.0369 (19)	0.0376 (19)	0.047 (2)	−0.0020 (16)	0.0048 (18)	−0.0023 (17)
C17	0.0351 (19)	0.042 (2)	0.047 (2)	−0.0002 (17)	−0.0058 (18)	0.0055 (17)
C18	0.042 (2)	0.050 (2)	0.044 (2)	−0.0066 (19)	0.0008 (19)	0.0034 (18)
C20	0.034 (2)	0.058 (3)	0.057 (3)	−0.0103 (19)	−0.004 (2)	−0.001 (2)
C21	0.042 (2)	0.045 (2)	0.056 (3)	−0.0056 (18)	−0.016 (2)	−0.001 (2)
C22	0.035 (2)	0.058 (3)	0.070 (3)	−0.004 (2)	−0.009 (2)	0.002 (3)
C23	0.034 (2)	0.069 (3)	0.113 (5)	0.001 (2)	−0.016 (3)	0.001 (3)
C211	0.036 (2)	0.052 (2)	0.070 (3)	0.0092 (18)	0.007 (2)	−0.001 (2)
C311	0.045 (2)	0.053 (3)	0.137 (6)	−0.013 (2)	0.012 (3)	0.005 (3)
O11P	0.0286 (14)	0.0553 (19)	0.109 (3)	−0.0012 (14)	−0.0128 (18)	−0.009 (2)
O12P	0.0405 (16)	0.0462 (17)	0.107 (3)	0.0017 (14)	−0.014 (2)	−0.009 (2)
O21P	0.0410 (15)	0.0510 (17)	0.080 (2)	0.0003 (14)	−0.0163 (17)	0.0102 (17)
O22P	0.0440 (17)	0.067 (2)	0.074 (2)	0.0182 (16)	0.0005 (18)	−0.0104 (18)
O31P	0.0398 (18)	0.071 (2)	0.153 (4)	0.0016 (18)	−0.025 (3)	0.001 (3)
O32P	0.0498 (19)	0.080 (3)	0.098 (3)	−0.0277 (19)	−0.006 (2)	0.010 (2)
N31P	0.0349 (17)	0.062 (2)	0.068 (3)	−0.0073 (18)	−0.0094 (19)	−0.004 (2)
C1P	0.0293 (17)	0.044 (2)	0.048 (2)	0.0053 (16)	−0.0064 (18)	−0.0016 (19)
C2P	0.0302 (18)	0.047 (2)	0.043 (2)	−0.0014 (16)	−0.0028 (17)	0.0010 (18)
C3P	0.0306 (18)	0.051 (2)	0.052 (2)	−0.0040 (18)	−0.0060 (19)	−0.0017 (19)
C4P	0.051 (3)	0.045 (2)	0.076 (3)	−0.008 (2)	−0.010 (3)	0.000 (2)
C5P	0.050 (2)	0.044 (2)	0.088 (4)	0.005 (2)	−0.014 (3)	−0.011 (2)
C6P	0.0327 (19)	0.057 (3)	0.069 (3)	0.0062 (19)	−0.010 (2)	−0.006 (2)
C11P	0.0294 (17)	0.047 (2)	0.057 (3)	0.0001 (17)	−0.0095 (18)	0.002 (2)
C21P	0.0253 (17)	0.043 (2)	0.066 (3)	0.0006 (16)	−0.010 (2)	−0.002 (2)
O1W	0.062 (2)	0.078 (3)	0.190 (5)	−0.007 (2)	0.027 (3)	0.035 (3)
O2W	0.096 (3)	0.078 (3)	0.089 (3)	−0.003 (2)	−0.005 (3)	−0.026 (2)

Geometric parameters (Å, º)

O21—C2	1.374 (5)	C15—C16	1.508 (6)
O21—C211	1.424 (5)	C17—C18	1.507 (5)
O24—C12	1.423 (5)	C20—C21	1.496 (6)
O24—C23	1.436 (6)	C21—C22	1.311 (6)
O25—C10	1.228 (5)	C22—C23	1.501 (8)
O31—C3	1.371 (5)	C1—H1	0.9672
O31—C311	1.405 (6)	C4—H4	0.9474
O11P—C11P	1.308 (5)	C8—H8	0.9555
O12P—C11P	1.207 (5)	C11—H11B	0.9743
O21P—C21P	1.241 (6)	C11—H11A	0.9496
O22P—C21P	1.258 (6)	C12—H12	0.9509
O31P—N31P	1.198 (6)	C13—H13	0.9612
O32P—N31P	1.229 (6)	C14—H14	0.9595
O11P—H11P	1.01 (9)	C15—H15A	0.9616
O1W—H12W	1.0132	C15—H15B	0.9629
O1W—H11W	0.9482	C16—H16	0.9682
O2W—H21W	0.9283	C17—H17B	0.9541
O2W—H22W	0.8929	C17—H17A	0.9590
N9—C8	1.486 (5)	C18—H18B	0.9540
N9—C10	1.355 (5)	C18—H18A	0.9517
N9—C5	1.414 (5)	C20—H20B	0.9529
N19—C16	1.541 (5)	C20—H20A	0.9624
N19—C18	1.509 (6)	C22—H22	0.9756
N19—C20	1.513 (6)	C23—H23B	0.9600
N19—H19	0.96 (5)	C23—H23A	0.9664
N31P—C3P	1.481 (5)	C1P—C6P	1.393 (6)
C1—C2	1.374 (6)	C1P—C2P	1.408 (5)
C1—C6	1.393 (5)	C1P—C11P	1.503 (6)
C2—C3	1.418 (6)	C2P—C21P	1.517 (6)
C3—C4	1.382 (6)	C2P—C3P	1.389 (6)
C4—C5	1.408 (6)	C3P—C4P	1.381 (6)
C5—C6	1.376 (5)	C4P—C5P	1.372 (7)
C6—C7	1.517 (5)	C5P—C6P	1.373 (7)
C7—C16	1.539 (6)	C4P—H4P	0.9476
C7—C17	1.532 (6)	C5P—H5P	0.9531
C7—C8	1.568 (5)	C6P—H6P	0.9499
C8—C13	1.521 (6)	C211—H21B	0.9655
C10—C11	1.509 (6)	C211—H21C	0.9510
C11—C12	1.538 (6)	C211—H21A	0.9487
C12—C13	1.523 (6)	C311—H31B	0.9793
C13—C14	1.540 (6)	C311—H31C	0.9475
C14—C15	1.523 (6)	C311—H31A	0.9491
C14—C21	1.527 (6)
C2—O21—C211	115.5 (3)	C10—C11—H11A	109.21
C12—O24—C23	115.2 (4)	O24—C12—H12	108.52
C3—O31—C311	117.3 (3)	C11—C12—H12	108.72
C11P—O11P—H11P	111 (5)	C13—C12—H12	108.64
H11W—O1W—H12W	101.81	C12—C13—H13	105.73
H21W—O2W—H22W	125.45	C8—C13—H13	104.97
C8—N9—C10	119.3 (3)	C14—C13—H13	105.60
C5—N9—C10	126.9 (3)	C21—C14—H14	109.49
C5—N9—C8	109.1 (3)	C13—C14—H14	107.85
C16—N19—C18	107.0 (3)	C15—C14—H14	109.19
C16—N19—C20	113.5 (3)	C16—C15—H15A	110.09
C18—N19—C20	112.0 (3)	C16—C15—H15B	109.63
C18—N19—H19	107 (3)	C14—C15—H15B	110.70
C20—N19—H19	114 (3)	C14—C15—H15A	110.01
C16—N19—H19	103 (3)	H15A—C15—H15B	107.53
O31P—N31P—C3P	119.0 (4)	C15—C16—H16	108.42
O32P—N31P—C3P	117.2 (4)	N19—C16—H16	108.21
O31P—N31P—O32P	123.8 (4)	C7—C16—H16	108.51
C2—C1—C6	119.0 (4)	H17A—C17—H17B	108.48
O21—C2—C3	114.0 (3)	C7—C17—H17A	111.90
C1—C2—C3	120.3 (4)	C18—C17—H17A	110.16
O21—C2—C1	125.7 (4)	C7—C17—H17B	112.17
O31—C3—C4	124.0 (4)	C18—C17—H17B	110.08
C2—C3—C4	121.2 (4)	C17—C18—H18B	110.57
O31—C3—C2	114.8 (3)	N19—C18—H18A	111.13
C3—C4—C5	117.1 (4)	C17—C18—H18A	111.15
C4—C5—C6	121.8 (4)	H18A—C18—H18B	108.84
N9—C5—C4	127.3 (3)	N19—C18—H18B	110.32
N9—C5—C6	110.9 (3)	H20A—C20—H20B	108.20
C5—C6—C7	110.9 (3)	N19—C20—H20B	110.36
C1—C6—C7	128.5 (4)	N19—C20—H20A	109.61
C1—C6—C5	120.5 (4)	C21—C20—H20A	108.79
C6—C7—C8	102.1 (3)	C21—C20—H20B	110.01
C8—C7—C17	111.8 (3)	C21—C22—H22	119.30
C16—C7—C17	101.8 (3)	C23—C22—H22	117.05
C6—C7—C17	112.7 (3)	O24—C23—H23B	110.16
C8—C7—C16	113.9 (3)	H23A—C23—H23B	107.31
C6—C7—C16	114.9 (3)	C22—C23—H23A	107.83
N9—C8—C13	104.6 (3)	O24—C23—H23A	109.42
C7—C8—C13	117.6 (3)	C22—C23—H23B	110.36
N9—C8—C7	105.0 (3)	C2P—C1P—C11P	119.9 (4)
N9—C10—C11	114.7 (4)	C2P—C1P—C6P	120.3 (4)
O25—C10—N9	123.4 (4)	C6P—C1P—C11P	119.7 (3)
O25—C10—C11	121.9 (4)	C1P—C2P—C3P	115.9 (4)
C10—C11—C12	116.5 (4)	C1P—C2P—C21P	122.3 (4)
O24—C12—C11	105.1 (3)	C3P—C2P—C21P	121.8 (3)
C11—C12—C13	110.3 (3)	C2P—C3P—C4P	124.0 (4)
O24—C12—C13	115.3 (4)	N31P—C3P—C2P	120.1 (4)
C12—C13—C14	119.5 (3)	N31P—C3P—C4P	115.9 (4)
C8—C13—C12	106.7 (3)	C3P—C4P—C5P	118.8 (4)
C8—C13—C14	113.2 (3)	C4P—C5P—C6P	119.8 (4)
C13—C14—C15	106.5 (3)	C1P—C6P—C5P	121.3 (4)
C15—C14—C21	109.9 (4)	O11P—C11P—O12P	125.0 (4)
C13—C14—C21	113.8 (4)	O12P—C11P—C1P	122.7 (3)
C14—C15—C16	108.9 (4)	O11P—C11P—C1P	112.3 (4)
N19—C16—C15	110.4 (3)	O22P—C21P—C2P	114.8 (4)
C7—C16—C15	115.9 (3)	O21P—C21P—C2P	117.9 (4)
N19—C16—C7	105.1 (3)	O21P—C21P—O22P	127.3 (4)
C7—C17—C18	104.0 (3)	C5P—C4P—H4P	121.29
N19—C18—C17	104.8 (3)	C3P—C4P—H4P	119.94
N19—C20—C21	109.8 (3)	C4P—C5P—H5P	119.70
C20—C21—C22	121.7 (4)	C6P—C5P—H5P	120.50
C14—C21—C22	123.1 (4)	C1P—C6P—H6P	119.06
C14—C21—C20	115.2 (3)	C5P—C6P—H6P	119.62
C21—C22—C23	123.5 (5)	O21—C211—H21C	110.89
O24—C23—C22	111.6 (4)	O21—C211—H21A	110.10
C6—C1—H1	120.73	O21—C211—H21B	110.04
C2—C1—H1	120.26	H21B—C211—H21C	108.00
C5—C4—H4	122.03	H21A—C211—H21B	108.29
C3—C4—H4	120.84	H21A—C211—H21C	109.46
C7—C8—H8	109.81	H31B—C311—H31C	107.20
N9—C8—H8	110.15	O31—C311—H31A	112.01
C13—C8—H8	109.29	O31—C311—H31B	109.08
C12—C11—H11A	108.66	O31—C311—H31C	111.52
C10—C11—H11B	107.37	H31A—C311—H31B	107.03
H11A—C11—H11B	107.39	H31A—C311—H31C	109.79
C12—C11—H11B	107.38
C211—O21—C2—C1	5.7 (7)	C8—C7—C17—C18	80.3 (4)
C211—O21—C2—C3	−173.6 (4)	C17—C7—C16—C15	152.9 (4)
C23—O24—C12—C11	172.2 (4)	C6—C7—C16—N19	152.9 (3)
C23—O24—C12—C13	−66.1 (5)	C6—C7—C16—C15	−84.9 (4)
C12—O24—C23—C22	86.2 (6)	C8—C7—C16—N19	−89.8 (4)
C311—O31—C3—C2	179.0 (5)	C6—C7—C8—N9	−13.8 (4)
C311—O31—C3—C4	0.2 (7)	C17—C7—C16—N19	30.7 (4)
C10—N9—C5—C4	16.2 (7)	C16—C7—C17—C18	−41.7 (4)
C5—N9—C8—C13	−110.8 (3)	C7—C8—C13—C14	37.2 (5)
C10—N9—C8—C7	170.8 (3)	N9—C8—C13—C12	−73.4 (4)
C10—N9—C8—C13	46.3 (4)	N9—C8—C13—C14	153.2 (3)
C5—N9—C10—O25	−19.3 (7)	C7—C8—C13—C12	170.6 (3)
C8—N9—C5—C4	171.1 (4)	N9—C10—C11—C12	−40.2 (6)
C8—N9—C5—C6	−7.9 (5)	O25—C10—C11—C12	141.2 (4)
C8—N9—C10—O25	−172.0 (4)	C10—C11—C12—O24	135.5 (4)
C10—N9—C5—C6	−162.8 (4)	C10—C11—C12—C13	10.6 (6)
C5—N9—C8—C7	13.7 (4)	O24—C12—C13—C8	−74.7 (4)
C5—N9—C10—C11	162.1 (4)	C11—C12—C13—C14	174.2 (4)
C8—N9—C10—C11	9.4 (5)	O24—C12—C13—C14	55.3 (5)
C20—N19—C16—C7	115.0 (4)	C11—C12—C13—C8	44.2 (4)
C18—N19—C16—C15	−134.7 (3)	C8—C13—C14—C21	61.8 (4)
C16—N19—C20—C21	−45.7 (5)	C12—C13—C14—C21	−65.1 (5)
C20—N19—C16—C15	−10.6 (5)	C12—C13—C14—C15	173.6 (4)
C18—N19—C16—C7	−9.0 (4)	C8—C13—C14—C15	−59.4 (4)
C16—N19—C18—C17	−16.9 (4)	C15—C14—C21—C22	176.1 (5)
C20—N19—C18—C17	−141.9 (3)	C13—C14—C21—C22	56.8 (6)
C18—N19—C20—C21	75.6 (5)	C13—C14—C21—C20	−122.4 (4)
O32P—N31P—C3P—C2P	152.3 (5)	C15—C14—C21—C20	−3.1 (5)
O31P—N31P—C3P—C2P	−28.1 (7)	C21—C14—C15—C16	−55.0 (5)
O31P—N31P—C3P—C4P	150.4 (5)	C13—C14—C15—C16	68.7 (4)
O32P—N31P—C3P—C4P	−29.2 (6)	C14—C15—C16—C7	−56.9 (5)
C6—C1—C2—O21	179.2 (5)	C14—C15—C16—N19	62.4 (4)
C2—C1—C6—C5	−0.6 (7)	C7—C17—C18—N19	36.6 (4)
C2—C1—C6—C7	−176.7 (4)	N19—C20—C21—C14	53.6 (5)
C6—C1—C2—C3	−1.6 (7)	N19—C20—C21—C22	−125.5 (5)
O21—C2—C3—O31	2.7 (7)	C20—C21—C22—C23	177.0 (5)
C1—C2—C3—C4	2.1 (8)	C14—C21—C22—C23	−2.1 (8)
O21—C2—C3—C4	−178.5 (4)	C21—C22—C23—O24	−64.2 (7)
C1—C2—C3—O31	−176.6 (4)	C11P—C1P—C2P—C3P	174.6 (4)
C2—C3—C4—C5	−0.4 (7)	C11P—C1P—C2P—C21P	−4.1 (6)
O31—C3—C4—C5	178.3 (4)	C2P—C1P—C6P—C5P	1.4 (7)
C3—C4—C5—C6	−1.9 (7)	C11P—C1P—C6P—C5P	−174.9 (5)
C3—C4—C5—N9	179.2 (4)	C2P—C1P—C11P—O11P	178.3 (4)
C4—C5—C6—C7	179.2 (4)	C6P—C1P—C2P—C3P	−1.7 (6)
N9—C5—C6—C7	−1.8 (5)	C6P—C1P—C2P—C21P	179.6 (4)
C4—C5—C6—C1	2.4 (7)	C6P—C1P—C11P—O12P	174.4 (5)
N9—C5—C6—C1	−178.5 (4)	C6P—C1P—C11P—O11P	−5.4 (6)
C1—C6—C7—C16	−50.0 (6)	C2P—C1P—C11P—O12P	−1.9 (7)
C1—C6—C7—C8	−173.7 (4)	C1P—C2P—C3P—C4P	1.2 (7)
C1—C6—C7—C17	66.1 (6)	C1P—C2P—C3P—N31P	179.5 (4)
C5—C6—C7—C17	−110.3 (4)	C1P—C2P—C21P—O21P	−79.6 (5)
C5—C6—C7—C8	9.9 (4)	C21P—C2P—C3P—N31P	−1.8 (7)
C5—C6—C7—C16	133.7 (4)	C21P—C2P—C3P—C4P	179.8 (6)
C16—C7—C8—N9	−138.2 (3)	C3P—C2P—C21P—O22P	−76.5 (6)
C17—C7—C8—C13	−137.2 (3)	C1P—C2P—C21P—O22P	102.1 (5)
C16—C7—C8—C13	−22.4 (5)	C3P—C2P—C21P—O21P	101.8 (5)
C17—C7—C8—N9	107.0 (3)	N31P—C3P—C4P—C5P	−178.6 (5)
C6—C7—C8—C13	102.1 (4)	C2P—C3P—C4P—C5P	−0.2 (8)
C8—C7—C16—C15	32.4 (5)	C3P—C4P—C5P—C6P	−0.2 (8)
C6—C7—C17—C18	−165.3 (3)	C4P—C5P—C6P—C1P	−0.4 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N19—H19···O21P^i	0.96 (5)	1.82 (5)	2.776 (5)	174 (4)
O11P—H11P···O22P^ii	1.01 (9)	1.57 (9)	2.563 (5)	169 (9)
O1W—H11W···O2W	0.95	2.08	2.919 (6)	146
O1W—H12W···O21P^i	1.01	1.98	2.921 (5)	153
O2W—H21W···O22P^iii	0.93	2.06	2.984 (6)	177
O2W—H22W···O21P	0.89	2.06	2.943 (6)	172
C1—H1···O1W	0.97	2.48	3.408 (6)	160
C4—H4···O25	0.95	2.40	2.936 (5)	116
C6P—H6P···O11P	0.95	2.35	2.692 (6)	101
C13—H13···O25^iv	0.96	2.50	3.301 (5)	141
C14—H14···O32P^v	0.96	2.54	3.429 (6)	154
C15—H15A···O2W^i	0.96	2.52	3.361 (6)	146
C17—H17B···O11P^iii	0.95	2.56	3.464 (5)	158
C20—H20B···O12P^i	0.95	2.58	3.113 (6)	115
C211—H21C···O1W	0.95	2.55	3.364 (6)	144
C23—H23B···O31^v	0.96	2.40	3.245 (6)	147

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