Chloro­bis(1,10-phenanthroline)copper(II) 5-nitro­isophthalate(1–) dihydrate

In the title compound, [CuCl(C₁₂H₈N₂)₂](C₈H₄NO₆)·2H₂O, the coordination geometry of the Cu atom is best described as distorted trigonal bipyramidal, made up of four N atoms of two phenanthroline mol­ecules and one chloride anion. The 5-nitro­isophthalate(1−) anion is uncomplexed and balances the charge. π–π stacking and intermolecular hydrogen-bond interactions link the components units into a three-dimensional network structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.103
• wR factor = 0.204
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
RFACG01_ALERT_3_C  The value of the R factor is > 0.10
            R factor given   0.103
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N5
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.59
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O3
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         13
PLAT417_ALERT_2_C Short Inter D-H..H-D       H2A    ..  H7A     ..       2.15 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.80(5), Rep   0.805(19) ......       2.63 su-Rat
              O7   -H7A     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.83(7), Rep     0.83(2) ......       3.50 su-Rat
              O8   -H8A     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.82(6), Rep     0.82(2) ......       3.00 su-Rat
              O8   -H8B     1.555   1.555

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Chlorobis(1,10-phenanthroline)copper(II) 5-nitroisophthalate(1-) dihydrate

Crystal data

[CuCl(C12H8N2)2](C8H4NO6)·2H2O	Z = 2
Mr = 705.55	F(000) = 722
Triclinic, P1	Dx = 1.566 Mg m^−3
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 10.5099 (13) Å	Cell parameters from 476 reflections
b = 12.1597 (14) Å	θ = 2.6–24.1°
c = 12.5348 (14) Å	µ = 0.88 mm^−1
α = 72.798 (3)°	T = 298 K
β = 84.990 (2)°	Rod, blue
γ = 77.968 (3)°	0.13 × 0.06 × 0.05 mm
V = 1496.1 (3) Å^3

Data collection

Bruker APEX area-detector diffractometer	5344 independent reflections
Radiation source: fine-focus sealed tube	3112 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.097
φ and ω scans	θmax = 25.2°, θmin = 1.7°
Absorption correction: integration (SADABS; Bruker, 2002)	h = −12→12
Tmin = 0.894, Tmax = 0.957	k = −14→14
11046 measured reflections	l = −15→15

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)] = 0.103	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.204	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0578P)^2 + 0.4686P] where P = (Fo^2 + 2Fc^2)/3
5344 reflections	(Δ/σ)max = 0.003
437 parameters	Δρmax = 0.49 e Å^−3
6 restraints	Δρmin = −0.44 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
Cu1	0.26184 (9)	0.49728 (8)	0.30213 (8)	0.0302 (3)
Cl1	0.4402 (2)	0.36824 (19)	0.3863 (2)	0.0509 (7)
O1	0.2263 (7)	0.9229 (7)	0.6847 (6)	0.085 (3)
O2	0.3405 (6)	1.0228 (5)	0.7469 (5)	0.0510 (17)
H2A	0.4130	0.9814	0.7589	0.077*
O3	0.3015 (6)	1.0220 (5)	1.1377 (5)	0.0518 (18)
O4	0.1602 (6)	0.9320 (5)	1.2542 (5)	0.0483 (17)
O5	−0.0752 (8)	0.7122 (7)	0.9404 (7)	0.095 (3)
O6	−0.1052 (8)	0.7212 (7)	1.1073 (6)	0.092 (3)
O7	0.4099 (7)	0.0468 (5)	0.2990 (5)	0.0522 (17)
O8	0.3724 (10)	0.9029 (11)	0.5063 (6)	0.143 (4)
N1	0.1512 (6)	0.3758 (6)	0.3277 (5)	0.0336 (17)
N2	0.0868 (6)	0.5927 (5)	0.3455 (5)	0.0306 (16)
N3	0.2745 (6)	0.5367 (6)	0.1216 (6)	0.0360 (17)
N4	0.3627 (6)	0.6272 (5)	0.2637 (5)	0.0316 (16)
N5	−0.0519 (8)	0.7450 (7)	1.0166 (7)	0.053 (2)
C1	0.1872 (9)	0.2648 (8)	0.3258 (7)	0.046 (2)
H1	0.2749	0.2366	0.3138	0.055*
C2	0.1019 (9)	0.1895 (9)	0.3405 (8)	0.055 (3)
H2	0.1319	0.1118	0.3407	0.066*
C3	−0.0292 (9)	0.2312 (9)	0.3550 (7)	0.048 (3)
H3A	−0.0893	0.1831	0.3618	0.057*
C4	−0.0705 (8)	0.3475 (8)	0.3594 (6)	0.034 (2)
C5	−0.2036 (9)	0.3972 (9)	0.3767 (7)	0.047 (2)
H5	−0.2675	0.3533	0.3814	0.056*
C6	−0.2378 (8)	0.5079 (9)	0.3865 (7)	0.046 (2)
H6	−0.3245	0.5383	0.3998	0.055*
C7	−0.1423 (8)	0.5774 (8)	0.3765 (7)	0.038 (2)
C8	−0.1693 (9)	0.6931 (8)	0.3880 (7)	0.048 (2)
H8	−0.2541	0.7286	0.4015	0.057*
C9	−0.0698 (9)	0.7508 (8)	0.3791 (7)	0.048 (2)
H9	−0.0864	0.8260	0.3875	0.058*
C10	0.0576 (8)	0.6983 (7)	0.3574 (6)	0.039 (2)
H10	0.1239	0.7401	0.3512	0.046*
C11	−0.0122 (8)	0.5335 (7)	0.3539 (6)	0.034 (2)
C12	0.0227 (8)	0.4161 (7)	0.3447 (6)	0.035 (2)
C13	0.2288 (9)	0.4915 (8)	0.0490 (8)	0.048 (2)
H13	0.1739	0.4380	0.0769	0.057*
C14	0.2591 (10)	0.5203 (8)	−0.0624 (8)	0.054 (3)
H14	0.2226	0.4888	−0.1088	0.064*
C15	0.3433 (10)	0.5956 (8)	−0.1063 (8)	0.054 (3)
H15	0.3644	0.6154	−0.1823	0.064*
C16	0.3972 (8)	0.6426 (7)	−0.0350 (7)	0.038 (2)
C17	0.4883 (8)	0.7207 (7)	−0.0708 (8)	0.046 (3)
H17	0.5168	0.7401	−0.1451	0.056*
C18	0.5329 (8)	0.7659 (8)	0.0002 (9)	0.053 (3)
H18	0.5907	0.8170	−0.0260	0.064*
C19	0.4928 (8)	0.7367 (7)	0.1173 (7)	0.035 (2)
C20	0.5310 (8)	0.7839 (7)	0.1950 (8)	0.045 (2)
H20	0.5872	0.8368	0.1729	0.054*
C21	0.4872 (8)	0.7537 (7)	0.3016 (8)	0.043 (2)
H21	0.5120	0.7863	0.3530	0.052*
C22	0.4039 (8)	0.6726 (7)	0.3347 (7)	0.038 (2)
H22	0.3767	0.6500	0.4093	0.046*
C23	0.4074 (7)	0.6591 (6)	0.1547 (7)	0.030 (2)
C24	0.3590 (7)	0.6110 (7)	0.0794 (7)	0.034 (2)
C25	0.2579 (9)	0.9594 (8)	0.7577 (8)	0.049 (3)
C26	0.1954 (7)	0.9226 (7)	0.8720 (7)	0.031 (2)
C27	0.2286 (7)	0.9577 (7)	0.9605 (7)	0.034 (2)
H27	0.2916	1.0039	0.9482	0.041*
C28	0.1708 (8)	0.9259 (7)	1.0669 (6)	0.032 (2)
C29	0.0764 (7)	0.8577 (7)	1.0848 (7)	0.033 (2)
H29	0.0349	0.8370	1.1545	0.039*
C30	0.0442 (7)	0.8208 (6)	0.9982 (7)	0.0303 (19)
C31	0.1027 (7)	0.8533 (7)	0.8921 (7)	0.034 (2)
H31	0.0790	0.8282	0.8348	0.041*
C32	0.2090 (9)	0.9603 (7)	1.1632 (7)	0.037 (2)
H7A	0.379 (7)	0.039 (6)	0.246 (3)	0.044*
H7B	0.413 (8)	0.007 (6)	0.362 (2)	0.044*
H8A	0.329 (6)	0.935 (6)	0.551 (5)	0.044*
H8B	0.433 (6)	0.847 (5)	0.525 (5)	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0239 (6)	0.0319 (6)	0.0384 (6)	−0.0132 (4)	0.0053 (4)	−0.0117 (5)
Cl1	0.0337 (13)	0.0452 (14)	0.0684 (18)	−0.0045 (11)	−0.0058 (12)	−0.0089 (12)
O1	0.096 (6)	0.143 (7)	0.063 (5)	−0.086 (6)	0.038 (4)	−0.068 (5)
O2	0.036 (4)	0.065 (4)	0.057 (4)	−0.017 (3)	0.015 (4)	−0.024 (4)
O3	0.072 (5)	0.052 (4)	0.046 (4)	−0.045 (4)	0.007 (3)	−0.015 (3)
O4	0.058 (4)	0.061 (4)	0.038 (4)	−0.035 (3)	0.009 (3)	−0.019 (3)
O5	0.125 (7)	0.123 (7)	0.074 (6)	−0.093 (6)	0.013 (5)	−0.044 (5)
O6	0.113 (7)	0.137 (7)	0.054 (5)	−0.099 (6)	0.030 (5)	−0.027 (5)
O7	0.057 (4)	0.063 (5)	0.047 (4)	−0.019 (4)	−0.004 (4)	−0.026 (4)
O8	0.126 (9)	0.202 (12)	0.057 (6)	0.044 (8)	0.021 (6)	−0.028 (7)
N1	0.031 (4)	0.036 (4)	0.039 (4)	−0.020 (3)	0.009 (3)	−0.013 (3)
N2	0.030 (4)	0.028 (4)	0.034 (4)	−0.006 (3)	0.001 (3)	−0.009 (3)
N3	0.036 (4)	0.037 (4)	0.046 (5)	−0.020 (3)	0.001 (3)	−0.019 (4)
N4	0.032 (4)	0.035 (4)	0.034 (4)	−0.012 (3)	−0.001 (3)	−0.015 (3)
N5	0.055 (6)	0.065 (6)	0.050 (6)	−0.033 (5)	−0.001 (5)	−0.016 (5)
C1	0.041 (6)	0.051 (6)	0.052 (6)	−0.017 (5)	0.005 (5)	−0.021 (5)
C2	0.063 (7)	0.059 (7)	0.065 (7)	−0.036 (6)	0.013 (6)	−0.039 (6)
C3	0.049 (6)	0.072 (7)	0.034 (6)	−0.036 (6)	0.012 (5)	−0.019 (5)
C4	0.034 (5)	0.051 (6)	0.022 (5)	−0.022 (4)	−0.001 (4)	−0.009 (4)
C5	0.040 (6)	0.064 (7)	0.043 (6)	−0.027 (5)	−0.007 (5)	−0.010 (5)
C6	0.021 (5)	0.075 (7)	0.037 (6)	−0.011 (5)	−0.003 (4)	−0.006 (5)
C7	0.030 (5)	0.048 (6)	0.031 (5)	−0.010 (4)	0.001 (4)	−0.003 (4)
C8	0.040 (6)	0.061 (7)	0.036 (6)	−0.002 (5)	0.002 (4)	−0.010 (5)
C9	0.059 (7)	0.044 (6)	0.040 (6)	−0.003 (5)	0.007 (5)	−0.016 (5)
C10	0.038 (5)	0.042 (6)	0.032 (5)	−0.006 (4)	0.005 (4)	−0.007 (4)
C11	0.037 (5)	0.042 (5)	0.021 (5)	−0.002 (4)	−0.007 (4)	−0.006 (4)
C12	0.043 (6)	0.046 (6)	0.021 (5)	−0.022 (5)	−0.001 (4)	−0.006 (4)
C13	0.054 (6)	0.052 (6)	0.045 (6)	−0.014 (5)	0.011 (5)	−0.026 (5)
C14	0.070 (7)	0.055 (7)	0.044 (6)	−0.005 (6)	−0.012 (5)	−0.029 (5)
C15	0.081 (8)	0.049 (6)	0.028 (5)	−0.005 (6)	−0.005 (5)	−0.008 (5)
C16	0.041 (5)	0.028 (5)	0.038 (5)	0.004 (4)	0.005 (4)	−0.008 (4)
C17	0.043 (6)	0.040 (6)	0.046 (6)	−0.009 (5)	0.021 (5)	−0.001 (5)
C18	0.034 (6)	0.047 (6)	0.074 (8)	−0.020 (5)	0.019 (5)	−0.009 (5)
C19	0.030 (5)	0.025 (5)	0.045 (6)	−0.007 (4)	0.005 (4)	−0.003 (4)
C20	0.045 (6)	0.036 (5)	0.054 (7)	−0.019 (5)	0.002 (5)	−0.007 (5)
C21	0.032 (5)	0.035 (5)	0.074 (7)	−0.005 (4)	−0.008 (5)	−0.031 (5)
C22	0.039 (5)	0.037 (5)	0.041 (6)	−0.013 (4)	−0.003 (4)	−0.012 (4)
C23	0.027 (5)	0.022 (4)	0.044 (6)	−0.005 (4)	−0.003 (4)	−0.013 (4)
C24	0.023 (5)	0.032 (5)	0.043 (6)	0.007 (4)	0.004 (4)	−0.012 (4)
C25	0.035 (6)	0.066 (7)	0.055 (7)	−0.026 (5)	0.010 (5)	−0.024 (5)
C26	0.029 (5)	0.030 (5)	0.037 (5)	−0.011 (4)	0.005 (4)	−0.012 (4)
C27	0.024 (5)	0.033 (5)	0.045 (6)	−0.006 (4)	−0.005 (4)	−0.010 (4)
C28	0.040 (5)	0.034 (5)	0.026 (5)	−0.016 (4)	0.005 (4)	−0.008 (4)
C29	0.022 (4)	0.037 (5)	0.034 (5)	−0.003 (4)	0.002 (4)	−0.004 (4)
C30	0.032 (5)	0.026 (5)	0.034 (5)	−0.011 (4)	0.000 (4)	−0.007 (4)
C31	0.028 (5)	0.039 (5)	0.046 (6)	−0.014 (4)	0.001 (4)	−0.021 (4)
C32	0.050 (6)	0.028 (5)	0.035 (6)	−0.009 (4)	−0.003 (5)	−0.011 (4)

Geometric parameters (Å, º)

Cu1—N1	2.002 (6)	C7—C8	1.424 (11)
Cu1—N4	2.002 (6)	C8—C9	1.356 (11)
Cu1—N2	2.082 (6)	C8—H8	0.9300
Cu1—N3	2.168 (7)	C9—C10	1.399 (11)
Cu1—Cl1	2.287 (2)	C9—H9	0.9300
O1—C25	1.225 (10)	C10—H10	0.9300
O2—C25	1.251 (9)	C11—C12	1.435 (11)
O2—H2A	0.8200	C13—C14	1.361 (11)
O3—C32	1.312 (9)	C13—H13	0.9300
O4—C32	1.192 (9)	C14—C15	1.371 (12)
O5—N5	1.199 (9)	C14—H14	0.9300
O6—N5	1.205 (9)	C15—C16	1.404 (11)
O7—H7A	0.805 (19)	C15—H15	0.9300
O7—H7B	0.796 (19)	C16—C24	1.415 (11)
O8—H8A	0.83 (2)	C16—C17	1.439 (11)
O8—H8B	0.82 (2)	C17—C18	1.335 (12)
N1—C1	1.330 (10)	C17—H17	0.9300
N1—C12	1.359 (10)	C18—C19	1.451 (12)
N2—C10	1.307 (9)	C18—H18	0.9300
N2—C11	1.363 (9)	C19—C20	1.389 (11)
N3—C13	1.357 (10)	C19—C23	1.391 (10)
N3—C24	1.362 (9)	C20—C21	1.343 (11)
N4—C22	1.321 (9)	C20—H20	0.9300
N4—C23	1.373 (9)	C21—C22	1.402 (10)
N5—C30	1.465 (10)	C21—H21	0.9300
C1—C2	1.375 (11)	C22—H22	0.9300
C1—H1	0.9300	C23—C24	1.423 (10)
C2—C3	1.381 (12)	C25—C26	1.504 (11)
C2—H2	0.9300	C26—C31	1.377 (10)
C3—C4	1.405 (11)	C26—C27	1.395 (10)
C3—H3A	0.9300	C27—C28	1.396 (10)
C4—C12	1.381 (10)	C27—H27	0.9300
C4—C5	1.429 (11)	C28—C29	1.384 (10)
C5—C6	1.358 (11)	C28—C32	1.499 (11)
C5—H5	0.9300	C29—C30	1.382 (10)
C6—C7	1.417 (11)	C29—H29	0.9300
C6—H6	0.9300	C30—C31	1.397 (10)
C7—C11	1.397 (11)	C31—H31	0.9300
N1—Cu1—N4	174.6 (3)	N1—C12—C11	116.4 (7)
N1—Cu1—N2	81.0 (3)	C4—C12—C11	120.5 (8)
N4—Cu1—N2	97.1 (2)	N3—C13—C14	123.5 (9)
N1—Cu1—N3	96.3 (2)	N3—C13—H13	118.3
N4—Cu1—N3	79.4 (2)	C14—C13—H13	118.3
N2—Cu1—N3	108.1 (2)	C13—C14—C15	120.2 (9)
N1—Cu1—Cl1	94.8 (2)	C13—C14—H14	119.9
N4—Cu1—Cl1	89.93 (19)	C15—C14—H14	119.9
N2—Cu1—Cl1	139.31 (19)	C14—C15—C16	119.1 (9)
N3—Cu1—Cl1	112.61 (19)	C14—C15—H15	120.5
C25—O2—H2A	109.5	C16—C15—H15	120.5
H7A—O7—H7B	131 (4)	C15—C16—C24	117.7 (8)
H8A—O8—H8B	123 (4)	C15—C16—C17	124.3 (9)
C1—N1—C12	117.6 (7)	C24—C16—C17	118.1 (8)
C1—N1—Cu1	128.4 (6)	C18—C17—C16	121.6 (8)
C12—N1—Cu1	114.0 (5)	C18—C17—H17	119.2
C10—N2—C11	117.8 (7)	C16—C17—H17	119.2
C10—N2—Cu1	131.1 (6)	C17—C18—C19	121.2 (8)
C11—N2—Cu1	111.0 (5)	C17—C18—H18	119.4
C13—N3—C24	117.0 (7)	C19—C18—H18	119.4
C13—N3—Cu1	132.6 (6)	C20—C19—C23	117.2 (8)
C24—N3—Cu1	109.8 (5)	C20—C19—C18	124.4 (8)
C22—N4—C23	117.8 (7)	C23—C19—C18	118.4 (8)
C22—N4—Cu1	126.4 (6)	C21—C20—C19	120.5 (8)
C23—N4—Cu1	115.2 (5)	C21—C20—H20	119.7
O5—N5—O6	123.7 (8)	C19—C20—H20	119.7
O5—N5—C30	118.5 (8)	C20—C21—C22	119.5 (8)
O6—N5—C30	117.7 (8)	C20—C21—H21	120.2
N1—C1—C2	123.7 (9)	C22—C21—H21	120.2
N1—C1—H1	118.2	N4—C22—C21	122.2 (8)
C2—C1—H1	118.2	N4—C22—H22	118.9
C1—C2—C3	118.7 (9)	C21—C22—H22	118.9
C1—C2—H2	120.6	N4—C23—C19	122.7 (7)
C3—C2—H2	120.6	N4—C23—C24	116.6 (7)
C2—C3—C4	119.1 (8)	C19—C23—C24	120.7 (8)
C2—C3—H3A	120.4	N3—C24—C16	122.5 (8)
C4—C3—H3A	120.4	N3—C24—C23	117.5 (7)
C12—C4—C3	117.8 (8)	C16—C24—C23	120.0 (8)
C12—C4—C5	119.2 (8)	O1—C25—O2	125.8 (9)
C3—C4—C5	123.0 (8)	O1—C25—C26	117.8 (8)
C6—C5—C4	120.8 (8)	O2—C25—C26	116.4 (8)
C6—C5—H5	119.6	C31—C26—C27	117.9 (7)
C4—C5—H5	119.6	C31—C26—C25	120.7 (8)
C5—C6—C7	120.5 (8)	C27—C26—C25	121.4 (7)
C5—C6—H6	119.8	C26—C27—C28	122.4 (8)
C7—C6—H6	119.8	C26—C27—H27	118.8
C11—C7—C6	120.2 (8)	C28—C27—H27	118.8
C11—C7—C8	115.8 (8)	C29—C28—C27	118.7 (7)
C6—C7—C8	124.0 (8)	C29—C28—C32	118.6 (7)
C9—C8—C7	119.0 (8)	C27—C28—C32	122.6 (7)
C9—C8—H8	120.5	C30—C29—C28	119.4 (7)
C7—C8—H8	120.5	C30—C29—H29	120.3
C8—C9—C10	120.7 (9)	C28—C29—H29	120.3
C8—C9—H9	119.7	C29—C30—C31	121.3 (7)
C10—C9—H9	119.7	C29—C30—N5	120.3 (7)
N2—C10—C9	122.3 (8)	C31—C30—N5	118.4 (7)
N2—C10—H10	118.8	C26—C31—C30	120.2 (8)
C9—C10—H10	118.8	C26—C31—H31	119.9
N2—C11—C7	124.4 (8)	C30—C31—H31	119.9
N2—C11—C12	116.8 (7)	O4—C32—O3	124.0 (8)
C7—C11—C12	118.7 (8)	O4—C32—C28	122.4 (8)
N1—C12—C4	123.0 (8)	O3—C32—C28	113.6 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8B···Cl1^i	0.82 (6)	2.64 (4)	3.420 (10)	160 (8)
O8—H8A···O1	0.83 (7)	1.90 (5)	2.642 (10)	149 (8)
O7—H7B···O8^ii	0.80 (3)	1.95 (3)	2.718 (11)	163 (7)
O7—H7A···O3^iii	0.80 (5)	1.73 (6)	2.526 (8)	176 (8)
O2—H2A···O7^i	0.82	1.94	2.651 (9)	145

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