Chloro­bis(1,10-phenanthroline-κ²N,N′)copper(II) 4-amino­benzene­sulfonate trihydrate

The crystal structure of the title compound, [CuCl(C₁₂H₈N₂)₂](C₆H₆NO₃S)·3H₂O, contains Cu^II cations five-coordinated by one chloride anion and four N atoms of two 1,10-phenanthroline ligands. Between the the 4-amino­benzene­sulfonate anions and the uncoordinated water mol­ecules inter­molecular hydrogen bonding is found.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.037
• wR factor = 0.103
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) .......         O4

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.09
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C30 H26 Cl1 Cu1 N5 O6 S1
            Atom count from _chemical_formula_moiety:C30 H28 Cl1 Cu1 N5 O6 S1
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      1.090
            Tmax scaled      0.758 Tmin scaled      0.708

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

   4 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
   2 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 (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1995); software used to prepare material for publication: SHELXTL.

Chlorobis(1,10-phenanthroline-κ²N,N')copper(II) 4-aminobenzenesulfonate trihydrate

Crystal data

[CuCl(C12H8N2)2](C6H6NO3S)·3H2O	Z = 2
Mr = 683.61	F(000) = 702
Triclinic, P1	Dx = 1.537 Mg m^−3
a = 8.1734 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.3367 (8) Å	Cell parameters from 2121 reflections
c = 14.9091 (10) Å	θ = 2.2–27.2°
α = 67.682 (1)°	µ = 0.95 mm^−1
β = 84.243 (1)°	T = 293 K
γ = 79.368 (1)°	Plate, green
V = 1476.81 (16) Å^3	0.35 × 0.33 × 0.29 mm

Data collection

Bruker SMART CCD area-detector diffractometer	5178 independent reflections
Radiation source: fine-focus sealed tube	3770 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −8→9
Tmin = 0.650, Tmax = 0.696	k = −11→15
7595 measured reflections	l = −15→17

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.056P)^2] where P = (Fo^2 + 2Fc^2)/3
5178 reflections	(Δ/σ)max = 0.001
409 parameters	Δρmax = 0.34 e Å^−3
15 restraints	Δρmin = −0.32 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)
Cu1	0.76030 (4)	0.96783 (3)	0.75822 (2)	0.04419 (13)
Cl1	1.00910 (9)	0.93488 (7)	0.82929 (5)	0.0587 (2)
N2	0.5366 (3)	1.06256 (18)	0.78544 (16)	0.0448 (6)
N3	0.6707 (3)	0.85383 (18)	0.87281 (16)	0.0447 (6)
N4	0.8271 (3)	1.08498 (18)	0.63819 (16)	0.0434 (6)
N5	0.7066 (3)	0.90686 (18)	0.65389 (16)	0.0425 (5)
C1	0.7441 (4)	0.7509 (2)	0.9153 (2)	0.0563 (8)
H1	0.8428	0.7264	0.8878	0.068*
C2	0.6784 (5)	0.6783 (3)	0.9997 (2)	0.0651 (9)
H2	0.7319	0.6062	1.0276	0.078*
C3	0.5352 (5)	0.7141 (3)	1.0404 (2)	0.0662 (10)
H3	0.4905	0.6663	1.0969	0.079*
C4	0.4537 (4)	0.8226 (3)	0.9982 (2)	0.0508 (8)
C5	0.3063 (4)	0.8686 (3)	1.0374 (2)	0.0654 (10)
H5	0.2573	0.8249	1.0944	0.078*
C6	0.2359 (4)	0.9747 (4)	0.9934 (3)	0.0677 (10)
H6	0.1401	1.0028	1.0208	0.081*
C7	0.3074 (4)	1.0442 (3)	0.9050 (2)	0.0527 (8)
C8	0.2397 (4)	1.1536 (3)	0.8543 (3)	0.0693 (10)
H8	0.1404	1.1850	0.8762	0.083*
C9	0.3203 (5)	1.2137 (3)	0.7729 (3)	0.0719 (10)
H9	0.2753	1.2863	0.7386	0.086*
C10	0.4701 (4)	1.1672 (2)	0.7403 (2)	0.0579 (8)
H10	0.5250	1.2105	0.6856	0.070*
C11	0.4544 (3)	1.0024 (2)	0.86657 (19)	0.0423 (7)
C12	0.5285 (3)	0.8900 (2)	0.91313 (18)	0.0419 (7)
C13	0.6470 (4)	0.8171 (2)	0.6633 (2)	0.0553 (8)
H13	0.6232	0.7691	0.7255	0.066*
C14	0.6184 (4)	0.7914 (3)	0.5845 (3)	0.0618 (9)
H14	0.5757	0.7280	0.5941	0.074*
C15	0.6537 (4)	0.8602 (3)	0.4936 (3)	0.0610 (9)
H15	0.6374	0.8432	0.4405	0.073*
C16	0.7149 (3)	0.9571 (2)	0.4792 (2)	0.0466 (7)
C17	0.7559 (4)	1.0342 (3)	0.3872 (2)	0.0581 (8)
H17	0.7401	1.0222	0.3314	0.070*
C18	0.8173 (4)	1.1242 (3)	0.3791 (2)	0.0604 (9)
H18	0.8429	1.1731	0.3177	0.073*
C19	0.8442 (3)	1.1468 (2)	0.4623 (2)	0.0470 (7)
C20	0.9116 (4)	1.2374 (2)	0.4600 (2)	0.0590 (9)
H20	0.9397	1.2895	0.4009	0.071*
C21	0.9354 (4)	1.2488 (2)	0.5436 (3)	0.0616 (9)
H21	0.9807	1.3086	0.5419	0.074*
C22	0.8928 (4)	1.1714 (2)	0.6330 (2)	0.0567 (8)
H22	0.9106	1.1805	0.6899	0.068*
C23	0.8039 (3)	1.0720 (2)	0.55480 (19)	0.0397 (6)
C24	0.7398 (3)	0.9758 (2)	0.56252 (19)	0.0393 (6)
S1	0.11579 (9)	0.56459 (7)	0.25897 (5)	0.0513 (2)
O1	0.0607 (4)	0.5000 (3)	0.35310 (19)	0.0876 (11)	0.83
O2	0.0197 (3)	0.5674 (3)	0.1819 (2)	0.0755 (9)	0.83
O3	0.1201 (4)	0.6771 (2)	0.2506 (3)	0.0928 (11)	0.83
O1'	0.0387 (16)	0.4640 (10)	0.2779 (11)	0.072 (4)*	0.17
O2'	0.1043 (16)	0.5851 (11)	0.3465 (8)	0.060 (3)*	0.17
O3'	0.0723 (17)	0.6525 (10)	0.1757 (8)	0.065 (3)*	0.17
N1	0.8207 (3)	0.3944 (2)	0.18581 (19)	0.0616 (7)
H1N1	0.8353	0.3835	0.1321	0.092*
H2N1	0.8923	0.4275	0.1973	0.092*
C25	0.6568 (4)	0.4313 (2)	0.2039 (2)	0.0447 (7)
C26	0.6151 (4)	0.4808 (2)	0.2719 (2)	0.0485 (7)
H26	0.6988	0.4881	0.3058	0.058*
C27	0.4504 (4)	0.5194 (2)	0.2899 (2)	0.0455 (7)
H27	0.4246	0.5523	0.3356	0.055*
C28	0.3242 (3)	0.5092 (2)	0.23981 (18)	0.0397 (6)
C29	0.3642 (4)	0.4591 (2)	0.1729 (2)	0.0439 (7)
H29	0.2800	0.4511	0.1397	0.053*
C30	0.5272 (4)	0.4208 (2)	0.1551 (2)	0.0481 (7)
H30	0.5518	0.3873	0.1098	0.058*
O4	0.5364 (4)	0.3511 (2)	0.5332 (2)	0.1019 (9)
O5	0.2207 (3)	0.4668 (2)	0.52941 (18)	0.0965 (9)
H1O5	0.1408	0.4718	0.5663	0.145*
H2O5	0.1932	0.4862	0.4732	0.145*
O6	0.1333 (3)	0.6787 (2)	0.98344 (17)	0.0861 (8)
H1O6	0.0866	0.6591	1.0372	0.129*
H2O6	0.0945	0.7404	0.9468	0.129*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0521 (2)	0.0414 (2)	0.0359 (2)	−0.01438 (16)	0.00316 (15)	−0.00876 (15)
Cl1	0.0545 (5)	0.0843 (6)	0.0399 (4)	−0.0212 (4)	0.0013 (3)	−0.0218 (4)
N2	0.0562 (15)	0.0414 (13)	0.0366 (13)	−0.0098 (12)	−0.0039 (11)	−0.0125 (11)
N3	0.0476 (14)	0.0419 (13)	0.0391 (13)	−0.0120 (11)	−0.0002 (11)	−0.0071 (10)
N4	0.0500 (14)	0.0404 (13)	0.0408 (13)	−0.0116 (11)	0.0031 (11)	−0.0153 (10)
N5	0.0491 (14)	0.0382 (13)	0.0397 (13)	−0.0128 (11)	−0.0001 (10)	−0.0116 (10)
C1	0.059 (2)	0.0436 (18)	0.0573 (19)	−0.0136 (15)	−0.0050 (16)	−0.0056 (15)
C2	0.082 (3)	0.0495 (19)	0.052 (2)	−0.0173 (18)	−0.0135 (18)	0.0006 (16)
C3	0.088 (3)	0.065 (2)	0.0418 (18)	−0.042 (2)	−0.0048 (18)	−0.0018 (16)
C4	0.0550 (18)	0.069 (2)	0.0352 (16)	−0.0319 (16)	−0.0004 (14)	−0.0168 (15)
C5	0.068 (2)	0.101 (3)	0.0429 (19)	−0.046 (2)	0.0109 (17)	−0.032 (2)
C6	0.050 (2)	0.117 (3)	0.065 (2)	−0.033 (2)	0.0137 (17)	−0.059 (2)
C7	0.0454 (17)	0.073 (2)	0.0577 (19)	−0.0135 (16)	−0.0031 (15)	−0.0420 (17)
C8	0.050 (2)	0.084 (3)	0.095 (3)	−0.0001 (19)	−0.008 (2)	−0.059 (2)
C9	0.072 (2)	0.055 (2)	0.092 (3)	0.0138 (19)	−0.026 (2)	−0.036 (2)
C10	0.069 (2)	0.0459 (18)	0.058 (2)	−0.0044 (17)	−0.0145 (17)	−0.0174 (15)
C11	0.0400 (15)	0.0552 (18)	0.0420 (16)	−0.0126 (13)	−0.0044 (13)	−0.0263 (14)
C12	0.0476 (17)	0.0495 (17)	0.0329 (14)	−0.0196 (14)	−0.0013 (13)	−0.0147 (13)
C13	0.066 (2)	0.0443 (17)	0.0558 (19)	−0.0191 (15)	−0.0009 (16)	−0.0137 (15)
C14	0.067 (2)	0.0495 (19)	0.080 (3)	−0.0150 (17)	−0.0075 (19)	−0.0329 (18)
C15	0.056 (2)	0.072 (2)	0.069 (2)	−0.0026 (17)	−0.0117 (17)	−0.0419 (19)
C16	0.0411 (16)	0.0553 (18)	0.0445 (17)	0.0028 (14)	−0.0051 (13)	−0.0236 (14)
C17	0.059 (2)	0.077 (2)	0.0395 (17)	−0.0059 (18)	0.0012 (15)	−0.0259 (16)
C18	0.057 (2)	0.072 (2)	0.0340 (17)	0.0016 (18)	0.0069 (14)	−0.0070 (15)
C19	0.0407 (16)	0.0421 (16)	0.0446 (17)	0.0010 (13)	0.0078 (13)	−0.0065 (13)
C20	0.055 (2)	0.0405 (17)	0.061 (2)	−0.0089 (15)	0.0156 (16)	0.0003 (15)
C21	0.067 (2)	0.0361 (17)	0.076 (2)	−0.0196 (15)	0.0148 (19)	−0.0143 (16)
C22	0.065 (2)	0.0479 (18)	0.062 (2)	−0.0175 (16)	0.0069 (16)	−0.0239 (16)
C23	0.0358 (14)	0.0393 (15)	0.0385 (15)	−0.0034 (12)	0.0034 (12)	−0.0104 (12)
C24	0.0347 (14)	0.0384 (15)	0.0405 (15)	−0.0034 (12)	0.0018 (12)	−0.0118 (12)
S1	0.0476 (4)	0.0639 (5)	0.0445 (4)	−0.0124 (4)	0.0066 (3)	−0.0227 (4)
O1	0.0675 (19)	0.115 (3)	0.0478 (17)	−0.0070 (18)	0.0250 (15)	−0.0039 (17)
O2	0.0497 (16)	0.122 (3)	0.0620 (18)	−0.0123 (17)	−0.0030 (14)	−0.0421 (18)
O3	0.071 (2)	0.064 (2)	0.157 (3)	−0.0016 (16)	0.001 (2)	−0.062 (2)
N1	0.0544 (16)	0.0597 (17)	0.0685 (18)	−0.0027 (13)	0.0039 (14)	−0.0257 (14)
C25	0.0517 (18)	0.0341 (15)	0.0413 (16)	−0.0109 (13)	0.0037 (14)	−0.0057 (12)
C26	0.0509 (18)	0.0485 (17)	0.0441 (16)	−0.0117 (14)	−0.0023 (14)	−0.0129 (14)
C27	0.0582 (19)	0.0444 (16)	0.0350 (15)	−0.0147 (14)	0.0053 (13)	−0.0145 (12)
C28	0.0487 (16)	0.0352 (14)	0.0358 (15)	−0.0173 (13)	0.0044 (12)	−0.0105 (12)
C29	0.0499 (17)	0.0445 (16)	0.0430 (16)	−0.0172 (14)	0.0023 (13)	−0.0190 (13)
C30	0.064 (2)	0.0405 (16)	0.0467 (17)	−0.0173 (15)	0.0093 (15)	−0.0229 (13)
O4	0.111 (2)	0.094 (2)	0.087 (2)	−0.0068 (17)	−0.0092 (17)	−0.0215 (16)
O5	0.0644 (16)	0.142 (3)	0.0701 (17)	−0.0028 (16)	0.0069 (13)	−0.0331 (17)
O6	0.0956 (19)	0.0935 (19)	0.0601 (15)	0.0024 (15)	−0.0060 (14)	−0.0254 (14)

Geometric parameters (Å, º)

Cu1—N4	1.984 (2)	C16—C24	1.397 (4)
Cu1—N3	1.989 (2)	C16—C17	1.420 (4)
Cu1—N2	2.119 (2)	C17—C18	1.345 (4)
Cu1—N5	2.122 (2)	C17—H17	0.9300
Cu1—Cl1	2.2804 (9)	C18—C19	1.429 (4)
N2—C10	1.333 (4)	C18—H18	0.9300
N2—C11	1.363 (3)	C19—C20	1.405 (4)
N3—C1	1.325 (3)	C19—C23	1.411 (4)
N3—C12	1.348 (3)	C20—C21	1.349 (5)
N4—C22	1.332 (4)	C20—H20	0.9300
N4—C23	1.354 (3)	C21—C22	1.399 (4)
N5—C13	1.328 (4)	C21—H21	0.9300
N5—C24	1.357 (3)	C22—H22	0.9300
C1—C2	1.393 (4)	C23—C24	1.434 (4)
C1—H1	0.9300	S1—O3'	1.368 (10)
C2—C3	1.356 (5)	S1—O1	1.419 (3)
C2—H2	0.9300	S1—O2'	1.423 (10)
C3—C4	1.404 (5)	S1—O2	1.441 (3)
C3—H3	0.9300	S1—O3	1.465 (3)
C4—C12	1.404 (4)	S1—O1'	1.505 (11)
C4—C5	1.424 (5)	S1—C28	1.769 (3)
C5—C6	1.354 (5)	N1—C25	1.376 (4)
C5—H5	0.9300	N1—H1N1	0.8600
C6—C7	1.433 (5)	N1—H2N1	0.8601
C6—H6	0.9300	C25—C26	1.392 (4)
C7—C11	1.394 (4)	C25—C30	1.399 (4)
C7—C8	1.398 (5)	C26—C27	1.388 (4)
C8—C9	1.358 (5)	C26—H26	0.9300
C8—H8	0.9300	C27—C28	1.386 (4)
C9—C10	1.396 (5)	C27—H27	0.9300
C9—H9	0.9300	C28—C29	1.381 (4)
C10—H10	0.9300	C29—C30	1.374 (4)
C11—C12	1.433 (4)	C29—H29	0.9300
C13—C14	1.394 (4)	C30—H30	0.9300
C13—H13	0.9300	O5—H1O5	0.8200
C14—C15	1.355 (5)	O5—H2O5	0.8200
C14—H14	0.9300	O6—H1O6	0.8201
C15—C16	1.404 (4)	O6—H2O6	0.8201
C15—H15	0.9300
N4—Cu1—N3	174.18 (10)	C15—C16—C17	124.6 (3)
N4—Cu1—N2	95.70 (9)	C18—C17—C16	121.3 (3)
N3—Cu1—N2	80.49 (9)	C18—C17—H17	119.4
N4—Cu1—N5	80.59 (9)	C16—C17—H17	119.4
N3—Cu1—N5	96.22 (9)	C17—C18—C19	121.8 (3)
N2—Cu1—N5	106.64 (9)	C17—C18—H18	119.1
N4—Cu1—Cl1	93.93 (7)	C19—C18—H18	119.1
N3—Cu1—Cl1	91.87 (7)	C20—C19—C23	116.5 (3)
N2—Cu1—Cl1	126.75 (7)	C20—C19—C18	125.1 (3)
N5—Cu1—Cl1	126.60 (7)	C23—C19—C18	118.3 (3)
C10—N2—C11	117.4 (3)	C21—C20—C19	119.9 (3)
C10—N2—Cu1	131.7 (2)	C21—C20—H20	120.0
C11—N2—Cu1	110.82 (18)	C19—C20—H20	120.0
C1—N3—C12	119.0 (2)	C20—C21—C22	120.6 (3)
C1—N3—Cu1	125.9 (2)	C20—C21—H21	119.7
C12—N3—Cu1	114.87 (18)	C22—C21—H21	119.7
C22—N4—C23	118.7 (2)	N4—C22—C21	121.3 (3)
C22—N4—Cu1	126.6 (2)	N4—C22—H22	119.3
C23—N4—Cu1	114.75 (18)	C21—C22—H22	119.3
C13—N5—C24	117.4 (2)	N4—C23—C19	122.9 (3)
C13—N5—Cu1	131.6 (2)	N4—C23—C24	117.6 (2)
C24—N5—Cu1	110.98 (17)	C19—C23—C24	119.4 (3)
N3—C1—C2	122.3 (3)	N5—C24—C16	123.6 (3)
N3—C1—H1	118.9	N5—C24—C23	116.0 (2)
C2—C1—H1	118.9	C16—C24—C23	120.4 (2)
C3—C2—C1	119.0 (3)	O3'—S1—O1	145.4 (6)
C3—C2—H2	120.5	O3'—S1—O2'	117.1 (8)
C1—C2—H2	120.5	O1—S1—O2'	50.8 (5)
C2—C3—C4	120.6 (3)	O3'—S1—O2	53.0 (6)
C2—C3—H3	119.7	O1—S1—O2	114.0 (2)
C4—C3—H3	119.7	O2'—S1—O2	143.6 (5)
C3—C4—C12	116.5 (3)	O3'—S1—O3	58.5 (6)
C3—C4—C5	124.6 (3)	O1—S1—O3	111.5 (2)
C12—C4—C5	118.8 (3)	O2'—S1—O3	62.6 (6)
C6—C5—C4	121.4 (3)	O2—S1—O3	109.3 (2)
C6—C5—H5	119.3	O3'—S1—O1'	116.6 (9)
C4—C5—H5	119.3	O1—S1—O1'	57.8 (6)
C5—C6—C7	120.8 (3)	O2'—S1—O1'	108.2 (8)
C5—C6—H6	119.6	O2—S1—O1'	64.0 (6)
C7—C6—H6	119.6	O3—S1—O1'	156.5 (5)
C11—C7—C8	116.9 (3)	O3'—S1—C28	106.3 (6)
C11—C7—C6	119.0 (3)	O1—S1—C28	108.31 (15)
C8—C7—C6	124.0 (3)	O2'—S1—C28	108.7 (5)
C9—C8—C7	119.4 (3)	O2—S1—C28	107.68 (14)
C9—C8—H8	120.3	O3—S1—C28	105.58 (15)
C7—C8—H8	120.3	O1'—S1—C28	97.9 (5)
C8—C9—C10	120.5 (3)	C25—N1—H1N1	112.5
C8—C9—H9	119.8	C25—N1—H2N1	115.3
C10—C9—H9	119.8	H1N1—N1—H2N1	116.2
N2—C10—C9	121.8 (3)	N1—C25—C26	120.5 (3)
N2—C10—H10	119.1	N1—C25—C30	121.7 (3)
C9—C10—H10	119.1	C26—C25—C30	117.8 (3)
N2—C11—C7	123.9 (3)	C27—C26—C25	121.0 (3)
N2—C11—C12	116.1 (2)	C27—C26—H26	119.5
C7—C11—C12	120.0 (3)	C25—C26—H26	119.5
N3—C12—C4	122.6 (3)	C28—C27—C26	120.2 (3)
N3—C12—C11	117.6 (2)	C28—C27—H27	119.9
C4—C12—C11	119.9 (3)	C26—C27—H27	119.9
N5—C13—C14	123.1 (3)	C29—C28—C27	119.3 (3)
N5—C13—H13	118.5	C29—C28—S1	120.9 (2)
C14—C13—H13	118.5	C27—C28—S1	119.8 (2)
C15—C14—C13	119.1 (3)	C30—C29—C28	120.6 (3)
C15—C14—H14	120.5	C30—C29—H29	119.7
C13—C14—H14	120.5	C28—C29—H29	119.7
C14—C15—C16	120.3 (3)	C29—C30—C25	121.2 (3)
C14—C15—H15	119.9	C29—C30—H30	119.4
C16—C15—H15	119.9	C25—C30—H30	119.4
C24—C16—C15	116.6 (3)	H1O5—O5—H2O5	112.3
C24—C16—C17	118.8 (3)	H1O6—O6—H2O6	114.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O6^i	0.86	2.15	3.000 (4)	168
N1—H2N1···O1′^ii	0.86	2.01	2.826 (13)	157
N1—H2N1···O2^ii	0.86	2.23	3.040 (4)	157
O5—H1O5···O1^iii	0.82	2.00	2.822 (3)	174
O5—H1O5···O2′^iii	0.82	2.36	3.111 (13)	153
O5—H2O5···O2′	0.82	1.97	2.744 (12)	158
O5—H2O5···O1	0.82	2.12	2.900 (4)	160
O6—H1O6···O3′^iv	0.82	2.03	2.757 (13)	148
O6—H1O6···O2^iv	0.82	2.11	2.905 (4)	163
O6—H2O6···Cl1^v	0.82	2.53	3.348 (3)	173
N1—H2N1···O1′^ii	0.86	2.01	2.826 (13)	157
N1—H1N1···O6^i	0.86	2.15	3.000 (4)	168

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