N,N,N′,N′-Tetra­methyl­butane-1,4-diammonium bis­(p-amino­benzoate) 2.25-hydrate

The asymmetric unit of the title compound, C₈H₂₂N₂²⁺·2C₇H₆NO₂⁻·2.25H₂O, consists of half each of two centrosymmetric tetra­methyl­butane-1,4-diammonium cations, two p-amino­benzoate anions and 2.25 solvent water mol­ecules. As a characteristic feature of 4-amino­carboxylic acid, twisting of the carboxyl­ate group from the aromatic plane is observed in the p-amino­benzoate anions. Other noteworthy features are the `head-to-tail' chain and the formation of dimers through N—H...O and O—H...O hydrogen bonds involving amino groups, carboxylate groups and water mol­ecules. Futhermore, an intricate three-dimensional hydrogen-bonding network involving N—H...O and O—H...O is observed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.055
• wR factor = 0.178
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.97 Deg.
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N2
PLAT415_ALERT_2_B Short Inter D-H..H-X       H7C    ..  H32W    ..       1.98 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.12 Ratio
PLAT128_ALERT_4_C Non-standard setting of Space group C2/c    ....    I2/a
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H8B    ..  H6C     ..       1.84 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C7     ..  C7      ..       3.12 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      39.10 Deg.
              C6   -N2   -C6A     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.60 Deg.
              O3W  -O3W  -H31W    2.557   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          6
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          7
              H2 O

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003), Mercury (Macrae et al., 2006), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

N,N,N',N'-Tetramethylbutane-1,4-diammonium bis(p-aminobenzoate) 2.25-hydrate

Crystal data

C8H22N2^2+·2C7H6NO2^−·2.25H2O	F(000) = 1988
Mr = 459.07	Dx = 1.223 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -I 2ya	Cell parameters from 25 reflections
a = 20.4798 (9) Å	θ = 10.2–12.2°
b = 10.5692 (7) Å	µ = 0.09 mm^−1
c = 23.072 (18) Å	T = 293 K
β = 92.79 (5)°	Block, yellow
V = 4988 (4) Å^3	0.19 × 0.16 × 0.15 mm
Z = 8

Data collection

Nonius MACH3 sealed tube diffractometer	2396 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
ω/2θ scans	h = −18→24
Absorption correction: ψ scan (North et al., 1968)	k = −1→12
Tmin = 0.918, Tmax = 0.987	l = −18→27
4997 measured reflections	3 standard reflections every 60 min
4384 independent reflections	intensity decay: none

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.178	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0863P)^2 + 3.6364P] where P = (Fo^2 + 2Fc^2)/3
4384 reflections	(Δ/σ)max = 0.001
303 parameters	Δρmax = 0.45 e Å^−3
20 restraints	Δρmin = −0.41 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	Occ. (<1)
C1	0.26716 (18)	1.1067 (3)	0.84193 (14)	0.0628 (10)
H1A	0.3128	1.1051	0.8344	0.094*
H1B	0.2612	1.0769	0.8806	0.094*
H1C	0.2510	1.1917	0.8381	0.094*
C2	0.16004 (17)	1.0232 (3)	0.80985 (17)	0.0666 (10)
H2A	0.1369	0.9780	0.7791	0.100*
H2B	0.1444	1.1088	0.8109	0.100*
H2C	0.1529	0.9827	0.8462	0.100*
N1	0.23061 (12)	1.0233 (2)	0.79960 (10)	0.0447 (6)
H1	0.2355	1.0563	0.7636	0.054*
C3	0.25966 (16)	0.8935 (3)	0.80021 (13)	0.0491 (8)
H3A	0.2548	0.8561	0.8382	0.059*
H3B	0.3061	0.9001	0.7941	0.059*
C4	0.22845 (15)	0.8069 (3)	0.75444 (13)	0.0474 (7)
H4A	0.1860	0.7793	0.7665	0.057*
H4B	0.2220	0.8527	0.7182	0.057*
N2	0.60196 (14)	0.7895 (2)	0.48620 (11)	0.0587 (7)
H2	0.5890	0.7404	0.5159	0.070*
C7	0.6740 (2)	0.8019 (4)	0.4906 (2)	0.0943 (14)
H7A	0.6871	0.8438	0.5262	0.141*
H7B	0.6882	0.8506	0.4584	0.141*
H7C	0.6936	0.7194	0.4899	0.141*
C8	0.5809 (2)	0.7294 (4)	0.43051 (17)	0.0850 (13)
H8A	0.5928	0.7826	0.3990	0.127*
H8B	0.5344	0.7181	0.4289	0.127*
H8C	0.6019	0.6486	0.4275	0.127*
C11	0.30490 (14)	0.9416 (3)	0.62840 (12)	0.0416 (7)
C111	0.26051 (16)	1.0400 (3)	0.65109 (13)	0.0476 (8)
O11	0.27859 (11)	1.0960 (2)	0.69798 (9)	0.0571 (6)
O12	0.20753 (12)	1.0609 (2)	0.62412 (10)	0.0682 (7)
C12	0.28406 (15)	0.8661 (3)	0.58177 (12)	0.0458 (7)
H12	0.2432	0.8809	0.5637	0.055*
C13	0.32196 (15)	0.7703 (3)	0.56171 (13)	0.0489 (8)
H13	0.3062	0.7209	0.5307	0.059*
C14	0.38398 (15)	0.7457 (3)	0.58712 (13)	0.0483 (8)
N14	0.42095 (14)	0.6479 (3)	0.56838 (13)	0.0721 (9)
H141	0.4606	0.6378	0.5781	0.086*
H142	0.4080	0.5992	0.5408	0.086*
C15	0.40575 (16)	0.8223 (3)	0.63349 (14)	0.0584 (9)
H15	0.4471	0.8090	0.6509	0.070*
C16	0.36682 (16)	0.9171 (3)	0.65366 (13)	0.0525 (8)
H16	0.3822	0.9660	0.6849	0.063*
C21	0.58313 (14)	0.4275 (3)	0.60780 (13)	0.0445 (7)
C211	0.59579 (15)	0.5362 (3)	0.56845 (14)	0.0492 (8)
O21	0.56957 (11)	0.6423 (2)	0.57921 (10)	0.0582 (6)
O22	0.63049 (12)	0.5190 (2)	0.52647 (11)	0.0680 (7)
C22	0.61044 (15)	0.3097 (3)	0.59723 (14)	0.0498 (8)
H22	0.6386	0.3012	0.5670	0.060*
C23	0.59689 (15)	0.2054 (3)	0.63033 (14)	0.0515 (8)
H23	0.6163	0.1281	0.6225	0.062*
C24	0.55444 (15)	0.2147 (3)	0.67535 (14)	0.0514 (8)
N24	0.53876 (15)	0.1103 (3)	0.70773 (13)	0.0685 (8)
H241	0.5478	0.0374	0.6932	0.082*
H242	0.4995	0.1038	0.7202	0.082*
C25	0.52947 (16)	0.3339 (3)	0.68784 (14)	0.0534 (8)
H25	0.5028	0.3433	0.7191	0.064*
C26	0.54358 (15)	0.4374 (3)	0.65486 (13)	0.0500 (8)
H26	0.5263	0.5158	0.6642	0.060*
O1W	0.40149 (14)	1.1803 (3)	0.73928 (13)	0.0892 (9)
H11W	0.3631	1.1565	0.7280	0.134*
H12W	0.3986	1.2271	0.7691	0.134*
O2W	0.09565 (11)	1.1614 (2)	0.66221 (10)	0.0648 (7)
H21W	0.1314	1.1290	0.6522	0.097*
H22W	0.0858	1.2234	0.6398	0.097*
O3W	0.2369 (5)	1.0094 (11)	0.9668 (4)	0.082 (3)	0.25
H31W	0.2681	1.0073	0.9929	0.122*	0.25
H32W	0.2027	1.0332	0.9828	0.122*	0.25
C6	0.5797 (3)	0.9229 (5)	0.4955 (3)	0.0891 (12)	0.80
H6A	0.5988	0.9544	0.5320	0.107*	0.80
H6B	0.5945	0.9763	0.4646	0.107*	0.80
C5	0.5101 (3)	0.9285 (4)	0.4964 (3)	0.0891 (12)	0.80
H5A	0.4950	0.8787	0.5284	0.107*	0.80
H5B	0.4906	0.8947	0.4605	0.107*	0.80
C5A	0.5222 (10)	0.9879 (19)	0.4745 (7)	0.0891 (12)	0.20
H5C	0.4986	0.9825	0.4371	0.107*	0.20
H5D	0.5584	1.0467	0.4731	0.107*	0.20
C6A	0.5405 (10)	0.8652 (17)	0.4991 (11)	0.0891 (12)	0.20
H6C	0.5038	0.8094	0.4897	0.107*	0.20
H6D	0.5418	0.8763	0.5409	0.107*	0.20

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.085 (3)	0.0428 (18)	0.059 (2)	0.0029 (18)	−0.0147 (19)	−0.0115 (16)
C2	0.064 (2)	0.060 (2)	0.076 (2)	0.0131 (18)	0.0055 (19)	−0.0067 (19)
N1	0.0605 (16)	0.0346 (13)	0.0383 (13)	0.0052 (12)	−0.0037 (11)	−0.0016 (10)
C3	0.061 (2)	0.0358 (16)	0.0492 (18)	0.0046 (15)	−0.0058 (15)	0.0022 (14)
C4	0.0574 (19)	0.0337 (15)	0.0506 (18)	−0.0011 (14)	−0.0018 (15)	−0.0013 (14)
N2	0.073 (2)	0.0508 (16)	0.0509 (16)	0.0152 (15)	−0.0120 (14)	0.0008 (13)
C7	0.097 (3)	0.097 (3)	0.087 (3)	−0.038 (3)	−0.014 (2)	0.027 (3)
C8	0.106 (3)	0.082 (3)	0.064 (2)	0.014 (3)	−0.022 (2)	−0.020 (2)
C11	0.0490 (17)	0.0382 (16)	0.0376 (15)	0.0044 (13)	0.0045 (13)	0.0039 (13)
C111	0.062 (2)	0.0362 (16)	0.0453 (17)	0.0025 (15)	0.0094 (16)	0.0047 (14)
O11	0.0748 (15)	0.0474 (13)	0.0495 (13)	0.0090 (11)	0.0063 (11)	−0.0070 (11)
O12	0.0593 (15)	0.0698 (16)	0.0745 (16)	0.0246 (12)	−0.0070 (13)	−0.0115 (13)
C12	0.0428 (16)	0.0533 (18)	0.0410 (16)	0.0070 (15)	−0.0012 (13)	0.0004 (14)
C13	0.0473 (18)	0.0549 (19)	0.0442 (17)	0.0013 (15)	−0.0008 (14)	−0.0116 (15)
C14	0.0492 (18)	0.0474 (17)	0.0487 (18)	0.0059 (15)	0.0053 (14)	−0.0048 (14)
N14	0.0581 (18)	0.074 (2)	0.083 (2)	0.0240 (16)	−0.0072 (16)	−0.0294 (17)
C15	0.0510 (19)	0.066 (2)	0.056 (2)	0.0105 (17)	−0.0123 (16)	−0.0127 (17)
C16	0.060 (2)	0.0520 (19)	0.0445 (17)	0.0054 (16)	−0.0044 (15)	−0.0099 (15)
C21	0.0382 (16)	0.0449 (17)	0.0495 (17)	−0.0009 (14)	−0.0068 (14)	−0.0102 (14)
C211	0.0402 (17)	0.0449 (19)	0.061 (2)	−0.0050 (15)	−0.0099 (16)	−0.0073 (16)
O21	0.0587 (14)	0.0426 (12)	0.0726 (15)	0.0021 (11)	−0.0029 (11)	−0.0054 (11)
O22	0.0738 (16)	0.0599 (15)	0.0717 (16)	−0.0021 (13)	0.0182 (14)	−0.0027 (13)
C22	0.0451 (17)	0.0505 (19)	0.0532 (19)	0.0045 (15)	−0.0042 (14)	−0.0085 (15)
C23	0.0505 (18)	0.0434 (18)	0.059 (2)	0.0082 (15)	−0.0127 (16)	−0.0049 (16)
C24	0.0510 (19)	0.0506 (19)	0.0513 (18)	0.0006 (16)	−0.0123 (15)	0.0012 (16)
N24	0.073 (2)	0.0582 (18)	0.074 (2)	0.0027 (16)	−0.0009 (16)	0.0126 (16)
C25	0.0537 (19)	0.060 (2)	0.0465 (18)	0.0042 (16)	0.0015 (15)	−0.0049 (16)
C26	0.0506 (18)	0.0430 (18)	0.0556 (19)	0.0031 (15)	−0.0051 (15)	−0.0107 (15)
O1W	0.0816 (19)	0.088 (2)	0.099 (2)	−0.0106 (16)	0.0187 (16)	−0.0310 (16)
O2W	0.0607 (14)	0.0595 (15)	0.0746 (16)	0.0052 (12)	0.0068 (12)	0.0033 (12)
O3W	0.052 (6)	0.128 (9)	0.067 (6)	−0.012 (6)	0.018 (5)	0.020 (6)
C6	0.100 (3)	0.054 (2)	0.111 (3)	0.014 (2)	−0.021 (3)	−0.008 (2)
C5	0.100 (3)	0.054 (2)	0.111 (3)	0.014 (2)	−0.021 (3)	−0.008 (2)
C5A	0.100 (3)	0.054 (2)	0.111 (3)	0.014 (2)	−0.021 (3)	−0.008 (2)
C6A	0.100 (3)	0.054 (2)	0.111 (3)	0.014 (2)	−0.021 (3)	−0.008 (2)

Geometric parameters (Å, º)

C1—N1	1.490 (4)	N14—H142	0.8507
C1—H1A	0.9600	C15—C16	1.375 (4)
C1—H1B	0.9600	C15—H15	0.9300
C1—H1C	0.9600	C16—H16	0.9300
C2—N1	1.476 (4)	C21—C26	1.390 (4)
C2—H2A	0.9600	C21—C22	1.391 (4)
C2—H2B	0.9600	C21—C211	1.494 (4)
C2—H2C	0.9600	C211—O22	1.242 (4)
N1—C3	1.495 (4)	C211—O21	1.273 (4)
N1—H1	0.9100	C22—C23	1.378 (4)
C3—C4	1.515 (4)	C22—H22	0.9300
C3—H3A	0.9700	C23—C24	1.390 (5)
C3—H3B	0.9700	C23—H23	0.9300
C4—C4^i	1.513 (6)	C24—N24	1.379 (4)
C4—H4A	0.9700	C24—C25	1.395 (4)
C4—H4B	0.9700	N24—H241	0.8631
N2—C8	1.479 (4)	N24—H242	0.8696
N2—C7	1.480 (5)	C25—C26	1.372 (4)
N2—C6	1.500 (5)	C25—H25	0.9300
N2—C6A	1.533 (15)	C26—H26	0.9300
N2—H2	0.9100	O1W—H11W	0.8531
C7—H7A	0.9600	O1W—H12W	0.8520
C7—H7B	0.9600	O2W—H21W	0.8512
C7—H7C	0.9600	O2W—H22W	0.8523
C8—H8A	0.9600	O3W—O3W^ii	1.599 (19)
C8—H8B	0.9600	O3W—H31W	0.8563
C8—H8C	0.9600	O3W—H32W	0.8471
C11—C12	1.390 (4)	C6—C5	1.427 (7)
C11—C16	1.394 (4)	C6—H6A	0.9700
C11—C111	1.493 (4)	C6—H6B	0.9700
C111—O12	1.244 (4)	C5—C5^iii	1.578 (7)
C111—O11	1.272 (4)	C5—H5A	0.9700
C12—C13	1.370 (4)	C5—H5B	0.9700
C12—H12	0.9300	C5A—C6A	1.458 (17)
C13—C14	1.397 (4)	C5A—C5A^iii	1.541 (10)
C13—H13	0.9300	C5A—H5C	0.9700
C14—N14	1.364 (4)	C5A—H5D	0.9700
C14—C15	1.397 (4)	C6A—H6C	0.9700
N14—H141	0.8389	C6A—H6D	0.9700
N1—C1—H1A	109.5	N14—C14—C13	121.0 (3)
N1—C1—H1B	109.5	C15—C14—C13	117.6 (3)
H1A—C1—H1B	109.5	C14—N14—H141	123.9
N1—C1—H1C	109.5	C14—N14—H142	122.6
H1A—C1—H1C	109.5	H141—N14—H142	112.6
H1B—C1—H1C	109.5	C16—C15—C14	120.8 (3)
N1—C2—H2A	109.5	C16—C15—H15	119.6
N1—C2—H2B	109.5	C14—C15—H15	119.6
H2A—C2—H2B	109.5	C15—C16—C11	121.6 (3)
N1—C2—H2C	109.5	C15—C16—H16	119.2
H2A—C2—H2C	109.5	C11—C16—H16	119.2
H2B—C2—H2C	109.5	C26—C21—C22	117.3 (3)
C2—N1—C1	111.1 (3)	C26—C21—C211	122.8 (3)
C2—N1—C3	112.9 (2)	C22—C21—C211	119.9 (3)
C1—N1—C3	110.4 (2)	O22—C211—O21	122.9 (3)
C2—N1—H1	107.3	O22—C211—C21	118.9 (3)
C1—N1—H1	107.4	O21—C211—C21	118.1 (3)
C3—N1—H1	107.4	C23—C22—C21	121.7 (3)
N1—C3—C4	113.2 (2)	C23—C22—H22	119.1
N1—C3—H3A	108.9	C21—C22—H22	119.1
C4—C3—H3A	108.9	C22—C23—C24	120.5 (3)
N1—C3—H3B	108.9	C22—C23—H23	119.8
C4—C3—H3B	108.9	C24—C23—H23	119.8
H3A—C3—H3B	107.8	N24—C24—C23	121.2 (3)
C4^i—C4—C3	110.2 (3)	N24—C24—C25	120.9 (3)
C4^i—C4—H4A	109.6	C23—C24—C25	117.9 (3)
C3—C4—H4A	109.6	C24—N24—H241	116.4
C4^i—C4—H4B	109.6	C24—N24—H242	119.1
C3—C4—H4B	109.6	H241—N24—H242	106.1
H4A—C4—H4B	108.1	C26—C25—C24	121.1 (3)
C8—N2—C7	110.1 (3)	C26—C25—H25	119.4
C8—N2—C6	116.7 (3)	C24—C25—H25	119.4
C7—N2—C6	102.5 (3)	C25—C26—C21	121.3 (3)
C8—N2—C6A	100.7 (10)	C25—C26—H26	119.3
C7—N2—C6A	140.1 (9)	C21—C26—H26	119.3
C6—N2—C6A	39.1 (8)	H11W—O1W—H12W	108.5
C8—N2—H2	109.0	H21W—O2W—H22W	109.1
C7—N2—H2	109.0	O3W^ii—O3W—H31W	28.6
C6—N2—H2	109.0	O3W^ii—O3W—H32W	80.0
C6A—N2—H2	83.0	H31W—O3W—H32W	107.8
N2—C7—H7A	109.5	C5—C6—N2	110.6 (4)
N2—C7—H7B	109.5	C5—C6—H6A	109.5
H7A—C7—H7B	109.5	N2—C6—H6A	109.5
N2—C7—H7C	109.5	C5—C6—H6B	109.5
H7A—C7—H7C	109.5	N2—C6—H6B	109.5
H7B—C7—H7C	109.5	H6A—C6—H6B	108.1
N2—C8—H8A	109.5	C6—C5—C5^iii	108.0 (6)
N2—C8—H8B	109.5	C6—C5—H5A	110.1
H8A—C8—H8B	109.5	C5^iii—C5—H5A	110.1
N2—C8—H8C	109.5	C6—C5—H5B	110.1
H8A—C8—H8C	109.5	C5^iii—C5—H5B	110.1
H8B—C8—H8C	109.5	H5A—C5—H5B	108.4
C12—C11—C16	117.1 (3)	C6A—C5A—C5A^iii	90.0 (15)
C12—C11—C111	120.2 (3)	C6A—C5A—H5C	113.6
C16—C11—C111	122.7 (3)	C5A^iii—C5A—H5C	113.6
O12—C111—O11	123.6 (3)	C6A—C5A—H5D	113.6
O12—C111—C11	118.6 (3)	C5A^iii—C5A—H5D	113.6
O11—C111—C11	117.7 (3)	H5C—C5A—H5D	110.9
C13—C12—C11	121.9 (3)	C5A—C6A—N2	125.9 (15)
C13—C12—H12	119.0	C5A—C6A—H6C	105.8
C11—C12—H12	119.0	N2—C6A—H6C	105.8
C12—C13—C14	120.9 (3)	C5A—C6A—H6D	105.8
C12—C13—H13	119.5	N2—C6A—H6D	105.8
C14—C13—H13	119.5	H6C—C6A—H6D	106.2
N14—C14—C15	121.4 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O11	0.91	1.84	2.698 (4)	157
N2—H2···O21	0.91	1.85	2.758 (4)	175
N14—H141···O21	0.84	2.23	3.043 (4)	163
N14—H142···O22^iv	0.85	2.11	2.964 (4)	176
N24—H241···O2W^v	0.86	2.44	3.290 (4)	168
N24—H242···O1W^vi	0.87	2.23	3.030 (4)	153
O1W—H11W···O11	0.85	1.94	2.793 (4)	176
O1W—H12W···O2W^vii	0.85	1.97	2.820 (4)	173
O2W—H21W···O12	0.85	1.86	2.711 (3)	175
O2W—H22W···O21^viii	0.85	2.01	2.856 (4)	172

Symmetry codes: (iv) −x+1, −y+1, −z+1; (v) x+1/2, −y+1, z; (vi) x, y−1, z; (vii) −x+1/2, −y+5/2, −z+3/2; (viii) x−1/2, −y+2, z.