Methanol{tris­[2-(2-pyridylmethyl­eneamino)ethyl]amino-κ⁷N}calcium(II) bis­(perchlorate) methanol solvate

In the title compound, [Ca(C₂₄H₂₇N₇)(CH₃OH)](ClO₄)₂·CH₃OH, the Ca²⁺ ion is coordinated by all seven N atoms from the tris­[2-(2-pyridylmethyl­eneamino)eth­yl]amine ligand and by the O atom of a methanol mol­ecule, in an approximately square-anti­prismatic geometry.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.054
• wR factor = 0.149
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  O23    ..  C19     ..       2.87 Ang.

Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.580
           From the CIF: _refine_ls_abs_structure_Flack_su    0.050
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.58
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT214_ALERT_2_C Atom O24     (Anion/Solvent) ADP max/min Ratio         4.30 prola
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl2
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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           25.02
           From the CIF: _reflns_number_total               5546
           Count of symmetry unique reflns         3047
           Completeness (_total/calc)            182.02%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2499
           Fraction of Friedel pairs measured     0.820
           Are heavy atom types Z>Si present        yes
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
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

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

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX and ORTEP-3 for Windows (Farrugia, 1999); software used to prepare material for publication: WinGX.

Methanol{tris[2-(2-pyridylmethyleneamino)ethyl]amino-κ⁷N}calcium(II) bis(perchlorate) methanol solvate

Crystal data

[Ca(C24H27N7)(CH4O)](ClO4)2·CH4O	F(000) = 1496
Mr = 716.59	Dx = 1.459 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 7131 reflections
a = 18.3264 (5) Å	θ = 1.0–27.5°
b = 16.3163 (4) Å	µ = 0.42 mm^−1
c = 10.9066 (2) Å	T = 293 K
V = 3261.28 (13) Å^3	Prism, colourless
Z = 4	0.30 × 0.25 × 0.23 mm

Data collection

Nonius KappaCCD area-detector diffractometer	5546 independent reflections
Radiation source: fine-focus sealed tube	5077 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 25.0°, θmin = 3.6°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −21→21
Tmin = 0.884, Tmax = 0.910	k = −19→19
7131 measured reflections	l = −12→12

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)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.0963P)^2 + 3.5065P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
5546 reflections	Δρmax = 1.04 e Å^−3
418 parameters	Δρmin = −0.64 e Å^−3
1 restraint	Absolute structure: Flack (1983), with 2509 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.58 (5)

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
Ca1	−0.00265 (4)	0.77694 (4)	0.43989 (8)	0.02383 (19)
N1	−0.00895 (19)	0.9405 (2)	0.4491 (4)	0.0307 (8)
N2	0.09267 (19)	0.8244 (2)	0.2687 (3)	0.0294 (7)
N3	−0.1074 (2)	0.8403 (2)	0.3311 (3)	0.0331 (8)
N4	−0.1137 (2)	0.6711 (2)	0.4011 (3)	0.0327 (8)
N5	0.0207 (2)	0.6760 (2)	0.2730 (3)	0.0340 (8)
N6	0.00500 (19)	0.6464 (2)	0.5652 (3)	0.0313 (8)
N7	0.11178 (19)	0.7647 (2)	0.5799 (3)	0.0317 (8)
C1	−0.1793 (3)	0.7199 (3)	0.3741 (5)	0.0403 (11)
H1A	−0.1968	0.7451	0.4491	0.048*
H1B	−0.2173	0.6841	0.3433	0.048*
C2	−0.1636 (3)	0.7869 (3)	0.2792 (4)	0.0402 (11)
H2A	−0.1465	0.7627	0.2032	0.048*
H2B	−0.2075	0.8180	0.2622	0.048*
C3	−0.1150 (3)	0.9171 (3)	0.3228 (4)	0.0364 (10)
H3A	−0.1540	0.9383	0.2783	0.044*
C4	−0.0637 (3)	0.9735 (3)	0.3819 (4)	0.0350 (10)
C5	−0.0735 (3)	1.0576 (3)	0.3699 (5)	0.0460 (12)
H5A	−0.1110	1.0784	0.3217	0.055*
C6	−0.0262 (3)	1.1100 (3)	0.4312 (6)	0.0496 (12)
H6A	−0.0319	1.1664	0.4250	0.060*
C7	0.0287 (3)	1.0778 (3)	0.5004 (5)	0.0460 (11)
H7A	0.0609	1.1117	0.5422	0.055*
C8	0.0352 (3)	0.9931 (3)	0.5069 (4)	0.0381 (10)
H8A	0.0727	0.9715	0.5545	0.046*
C9	−0.0998 (3)	0.6122 (3)	0.2992 (4)	0.0388 (11)
H9A	−0.1228	0.6327	0.2251	0.047*
H9B	−0.1223	0.5601	0.3192	0.047*
C10	−0.0194 (3)	0.5986 (3)	0.2745 (5)	0.0393 (11)
H10A	0.0008	0.5632	0.3375	0.047*
H10B	−0.0135	0.5713	0.1961	0.047*
C11	0.0661 (2)	0.6887 (3)	0.1877 (4)	0.0337 (10)
H11A	0.0731	0.6491	0.1276	0.040*
C12	0.1080 (2)	0.7660 (3)	0.1828 (4)	0.0291 (9)
C13	0.1621 (3)	0.7769 (3)	0.0938 (4)	0.0368 (10)
H13A	0.1722	0.7354	0.0378	0.044*
C14	0.2001 (3)	0.8489 (3)	0.0900 (4)	0.0383 (10)
H14A	0.2357	0.8574	0.0306	0.046*
C15	0.1848 (2)	0.9083 (3)	0.1748 (4)	0.0361 (10)
H15A	0.2100	0.9578	0.1742	0.043*
C16	0.1307 (2)	0.8933 (3)	0.2621 (4)	0.0327 (9)
H16A	0.1207	0.9342	0.3191	0.039*
C17	−0.1242 (2)	0.6280 (3)	0.5181 (4)	0.0349 (10)
H17A	−0.1624	0.5874	0.5084	0.042*
H17B	−0.1402	0.6670	0.5796	0.042*
C18	−0.0554 (2)	0.5858 (3)	0.5629 (4)	0.0337 (10)
H18A	−0.0632	0.5638	0.6445	0.040*
H18B	−0.0430	0.5408	0.5086	0.040*
C19	0.0539 (3)	0.6394 (3)	0.6457 (4)	0.0342 (10)
H19A	0.0532	0.5944	0.6981	0.041*
C20	0.1120 (2)	0.7007 (3)	0.6586 (4)	0.0339 (10)
C21	0.1639 (3)	0.6927 (3)	0.7505 (5)	0.0416 (11)
H21A	0.1631	0.6477	0.8028	0.050*
C22	0.2169 (2)	0.7525 (3)	0.7634 (5)	0.0417 (11)
H22A	0.2523	0.7482	0.8242	0.050*
C23	0.2164 (2)	0.8182 (3)	0.6851 (4)	0.0358 (10)
H23A	0.2507	0.8598	0.6927	0.043*
C24	0.1631 (2)	0.8212 (3)	0.5935 (4)	0.0326 (9)
H24A	0.1637	0.8651	0.5392	0.039*
O2	−0.06395 (18)	0.80850 (19)	0.6330 (3)	0.0388 (7)
H2	−0.0550	0.7748	0.6866	0.058*
C25	−0.1119 (3)	0.8720 (3)	0.6751 (5)	0.0488 (13)
H25A	−0.1189	0.8668	0.7620	0.073*
H25B	−0.1582	0.8672	0.6343	0.073*
H25C	−0.0909	0.9245	0.6571	0.073*
Cl1	0.25486 (6)	0.56185 (6)	0.00376 (11)	0.0339 (2)
O11	0.2920 (2)	0.6387 (2)	0.0010 (4)	0.0556 (9)
O12	0.17860 (19)	0.5738 (2)	0.0160 (5)	0.0589 (11)
O13	0.2672 (3)	0.5197 (3)	−0.1067 (5)	0.0822 (15)
O14	0.2826 (3)	0.5123 (3)	0.1003 (5)	0.0792 (15)
Cl2	0.07537 (6)	0.34036 (6)	0.41604 (10)	0.0371 (3)
O21	0.0910 (5)	0.2991 (5)	0.5207 (5)	0.141 (3)
O22	0.0401 (3)	0.4155 (3)	0.4284 (6)	0.0846 (15)
O23	0.0266 (5)	0.2898 (4)	0.3453 (8)	0.133 (3)
O24	0.1268 (6)	0.3394 (8)	0.3282 (8)	0.228 (7)
O1	0.1724 (6)	0.5208 (6)	0.5405 (9)	0.157 (3)
H1	0.1466	0.4812	0.5244	0.236*
C26	0.1980 (6)	0.5600 (7)	0.4341 (11)	0.125 (4)
H26A	0.2244	0.6086	0.4565	0.187*
H26B	0.1574	0.5746	0.3829	0.187*
H26C	0.2298	0.5236	0.3902	0.187*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ca1	0.0299 (4)	0.0218 (4)	0.0197 (4)	0.0024 (3)	0.0014 (3)	−0.0012 (3)
N1	0.0360 (18)	0.0305 (18)	0.0256 (18)	0.0041 (14)	0.0027 (15)	−0.0011 (16)
N2	0.0374 (18)	0.0267 (18)	0.0242 (18)	0.0051 (14)	0.0029 (15)	−0.0010 (14)
N3	0.037 (2)	0.037 (2)	0.0251 (19)	0.0025 (16)	−0.0026 (15)	0.0027 (15)
N4	0.0396 (19)	0.0360 (19)	0.0224 (18)	−0.0020 (15)	0.0034 (15)	−0.0076 (15)
N5	0.046 (2)	0.0268 (19)	0.029 (2)	0.0011 (16)	0.0102 (16)	−0.0069 (15)
N6	0.036 (2)	0.028 (2)	0.030 (2)	0.0011 (14)	0.0101 (15)	0.0058 (15)
N7	0.0323 (18)	0.0326 (19)	0.0301 (19)	0.0066 (15)	0.0028 (15)	0.0078 (15)
C1	0.035 (2)	0.051 (3)	0.035 (3)	−0.013 (2)	−0.0008 (19)	−0.001 (2)
C2	0.041 (3)	0.045 (3)	0.035 (3)	−0.001 (2)	−0.014 (2)	−0.002 (2)
C3	0.037 (2)	0.043 (3)	0.029 (2)	0.011 (2)	−0.0023 (18)	0.0065 (19)
C4	0.044 (2)	0.030 (2)	0.031 (2)	0.0070 (19)	0.0060 (19)	0.0010 (17)
C5	0.046 (3)	0.032 (3)	0.060 (3)	0.011 (2)	0.005 (2)	0.013 (2)
C6	0.062 (3)	0.023 (2)	0.064 (3)	0.006 (2)	0.014 (3)	0.002 (2)
C7	0.054 (3)	0.036 (2)	0.048 (3)	−0.005 (2)	0.013 (3)	−0.007 (2)
C8	0.041 (2)	0.039 (2)	0.034 (2)	0.0076 (19)	0.000 (2)	0.000 (2)
C9	0.056 (3)	0.033 (2)	0.027 (2)	−0.012 (2)	0.005 (2)	−0.0121 (18)
C10	0.062 (3)	0.024 (2)	0.032 (2)	−0.004 (2)	0.011 (2)	−0.0048 (18)
C11	0.046 (3)	0.029 (2)	0.026 (2)	0.0046 (18)	0.0120 (19)	−0.0050 (17)
C12	0.038 (2)	0.029 (2)	0.021 (2)	0.0044 (17)	0.0040 (18)	0.0005 (16)
C13	0.047 (3)	0.035 (2)	0.029 (2)	0.0060 (19)	0.009 (2)	0.0006 (18)
C14	0.037 (2)	0.044 (3)	0.034 (2)	0.0004 (19)	0.0088 (19)	0.005 (2)
C15	0.038 (2)	0.038 (2)	0.032 (2)	−0.0062 (19)	0.0013 (19)	0.0034 (19)
C16	0.036 (2)	0.031 (2)	0.031 (2)	0.0020 (18)	0.0017 (19)	0.0002 (18)
C17	0.041 (2)	0.034 (2)	0.030 (2)	−0.0124 (18)	0.0072 (19)	−0.0028 (19)
C18	0.040 (2)	0.028 (2)	0.033 (2)	−0.0068 (18)	0.0052 (18)	0.0022 (18)
C19	0.045 (3)	0.028 (2)	0.030 (2)	0.0062 (19)	0.005 (2)	0.0081 (17)
C20	0.037 (2)	0.038 (2)	0.027 (2)	0.0106 (19)	0.0041 (18)	0.0053 (18)
C21	0.044 (3)	0.047 (3)	0.033 (2)	0.011 (2)	−0.001 (2)	0.012 (2)
C22	0.031 (2)	0.062 (3)	0.032 (3)	0.009 (2)	−0.0024 (19)	0.004 (2)
C23	0.024 (2)	0.051 (3)	0.032 (2)	0.0035 (18)	0.0061 (17)	0.001 (2)
C24	0.032 (2)	0.038 (2)	0.028 (2)	0.0048 (18)	0.0043 (17)	0.0047 (18)
O2	0.0562 (19)	0.0340 (17)	0.0261 (16)	0.0092 (14)	0.0143 (14)	−0.0017 (13)
C25	0.050 (3)	0.047 (3)	0.050 (3)	0.010 (2)	0.013 (2)	−0.008 (2)
Cl1	0.0371 (5)	0.0289 (5)	0.0356 (5)	0.0052 (4)	−0.0055 (4)	−0.0054 (4)
O11	0.052 (2)	0.041 (2)	0.074 (3)	−0.0049 (15)	−0.008 (2)	−0.0015 (19)
O12	0.0408 (19)	0.0391 (19)	0.097 (3)	0.0068 (15)	0.016 (2)	0.003 (2)
O13	0.086 (3)	0.090 (3)	0.070 (3)	−0.006 (3)	0.020 (3)	−0.047 (3)
O14	0.098 (4)	0.056 (3)	0.084 (3)	−0.007 (2)	−0.053 (3)	0.024 (2)
Cl2	0.0445 (6)	0.0366 (5)	0.0303 (5)	0.0061 (4)	−0.0014 (4)	−0.0026 (4)
O21	0.243 (8)	0.148 (6)	0.031 (3)	0.112 (6)	−0.013 (4)	0.007 (3)
O22	0.113 (4)	0.049 (2)	0.092 (4)	0.035 (2)	0.016 (3)	−0.009 (3)
O23	0.197 (8)	0.078 (4)	0.123 (6)	−0.023 (5)	−0.065 (6)	−0.018 (4)
O24	0.230 (10)	0.308 (13)	0.145 (7)	0.204 (10)	0.143 (8)	0.118 (8)
O1	0.185 (8)	0.149 (7)	0.138 (7)	0.030 (6)	−0.042 (7)	−0.027 (6)
C26	0.122 (7)	0.149 (9)	0.102 (7)	−0.071 (7)	0.050 (6)	−0.019 (7)

Geometric parameters (Å, º)

Ca1—O2	2.442 (3)	C11—C12	1.478 (6)
Ca1—N3	2.483 (4)	C11—H11A	0.930
Ca1—N5	2.492 (4)	C12—C13	1.399 (6)
Ca1—N6	2.535 (4)	C13—C14	1.366 (7)
Ca1—N7	2.602 (4)	C13—H13A	0.930
Ca1—N2	2.672 (4)	C14—C15	1.369 (7)
Ca1—N1	2.673 (3)	C14—H14A	0.930
Ca1—N4	2.702 (4)	C15—C16	1.397 (6)
N1—C8	1.338 (6)	C15—H15A	0.930
N1—C4	1.354 (6)	C16—H16A	0.930
N2—C16	1.326 (6)	C17—C18	1.517 (7)
N2—C12	1.365 (5)	C17—H17A	0.970
N3—C3	1.265 (6)	C17—H17B	0.970
N3—C2	1.461 (6)	C18—H18A	0.970
N4—C17	1.471 (6)	C18—H18B	0.970
N4—C1	1.472 (6)	C19—C20	1.467 (7)
N4—C9	1.490 (5)	C19—H19A	0.930
N5—C11	1.265 (6)	C20—C21	1.389 (6)
N5—C10	1.460 (6)	C21—C22	1.384 (8)
N6—C19	1.260 (6)	C21—H21A	0.930
N6—C18	1.484 (5)	C22—C23	1.370 (7)
N7—C24	1.325 (6)	C22—H22A	0.930
N7—C20	1.351 (5)	C23—C24	1.398 (6)
C1—C2	1.532 (7)	C23—H23A	0.930
C1—H1A	0.970	C24—H24A	0.930
C1—H1B	0.970	O2—C25	1.435 (6)
C2—H2A	0.970	O2—H2	0.820
C2—H2B	0.970	C25—H25A	0.960
C3—C4	1.465 (7)	C25—H25B	0.960
C3—H3A	0.930	C25—H25C	0.960
C4—C5	1.390 (7)	Cl1—O13	1.406 (4)
C5—C6	1.389 (8)	Cl1—O12	1.418 (4)
C5—H5A	0.930	Cl1—O14	1.421 (4)
C6—C7	1.362 (8)	Cl1—O11	1.427 (4)
C6—H6A	0.930	Cl2—O24	1.343 (6)
C7—C8	1.389 (7)	Cl2—O21	1.355 (5)
C7—H7A	0.930	Cl2—O22	1.394 (4)
C8—H8A	0.930	Cl2—O23	1.440 (6)
C9—C10	1.515 (7)	O1—C26	1.406 (13)
C9—H9A	0.970	O1—H1	0.820
C9—H9B	0.970	C26—H26A	0.960
C10—H10A	0.970	C26—H26B	0.960
C10—H10B	0.970	C26—H26C	0.960
O2—Ca1—N3	88.21 (12)	N4—C9—H9B	109.0
O2—Ca1—N5	148.03 (12)	C10—C9—H9B	109.0
N3—Ca1—N5	93.36 (13)	H9A—C9—H9B	107.8
O2—Ca1—N6	74.79 (11)	N5—C10—C9	111.4 (4)
N3—Ca1—N6	130.57 (13)	N5—C10—H10A	109.4
N5—Ca1—N6	80.14 (13)	C9—C10—H10A	109.4
O2—Ca1—N7	83.15 (11)	N5—C10—H10B	109.4
N3—Ca1—N7	159.39 (12)	C9—C10—H10B	109.4
N5—Ca1—N7	103.86 (13)	H10A—C10—H10B	108.0
N6—Ca1—N7	64.80 (12)	N5—C11—C12	120.6 (4)
O2—Ca1—N2	147.41 (11)	N5—C11—H11A	119.7
N3—Ca1—N2	92.92 (12)	C12—C11—H11A	119.7
N5—Ca1—N2	64.45 (12)	N2—C12—C13	122.2 (4)
N6—Ca1—N2	125.74 (11)	N2—C12—C11	117.6 (4)
N7—Ca1—N2	84.58 (11)	C13—C12—C11	120.2 (4)
O2—Ca1—N1	74.76 (11)	C14—C13—C12	119.5 (4)
N3—Ca1—N1	64.47 (12)	C14—C13—H13A	120.3
N5—Ca1—N1	134.01 (13)	C12—C13—H13A	120.3
N6—Ca1—N1	145.20 (13)	C13—C14—C15	119.0 (4)
N7—Ca1—N1	95.14 (11)	C13—C14—H14A	120.5
N2—Ca1—N1	76.43 (11)	C15—C14—H14A	120.5
O2—Ca1—N4	85.62 (11)	C14—C15—C16	118.8 (4)
N3—Ca1—N4	66.97 (12)	C14—C15—H15A	120.6
N5—Ca1—N4	65.93 (11)	C16—C15—H15A	120.6
N6—Ca1—N4	65.73 (12)	N2—C16—C15	124.0 (4)
N7—Ca1—N4	130.51 (11)	N2—C16—H16A	118.0
N2—Ca1—N4	124.60 (11)	C15—C16—H16A	118.0
N1—Ca1—N4	127.70 (11)	N4—C17—C18	112.8 (4)
C8—N1—C4	116.7 (4)	N4—C17—H17A	109.0
C8—N1—Ca1	129.2 (3)	C18—C17—H17A	109.0
C4—N1—Ca1	114.1 (3)	N4—C17—H17B	109.0
C16—N2—C12	116.6 (4)	C18—C17—H17B	109.0
C16—N2—Ca1	128.9 (3)	H17A—C17—H17B	107.8
C12—N2—Ca1	114.3 (3)	N6—C18—C17	108.9 (3)
C3—N3—C2	119.0 (4)	N6—C18—H18A	109.9
C3—N3—Ca1	122.1 (3)	C17—C18—H18A	109.9
C2—N3—Ca1	118.8 (3)	N6—C18—H18B	109.9
C17—N4—C1	109.0 (3)	C17—C18—H18B	109.9
C17—N4—C9	111.2 (3)	H18A—C18—H18B	108.3
C1—N4—C9	109.8 (4)	N6—C19—C20	121.4 (4)
C17—N4—Ca1	105.6 (2)	N6—C19—H19A	119.3
C1—N4—Ca1	107.5 (3)	C20—C19—H19A	119.3
C9—N4—Ca1	113.6 (3)	N7—C20—C21	122.2 (4)
C11—N5—C10	118.7 (4)	N7—C20—C19	117.7 (4)
C11—N5—Ca1	122.8 (3)	C21—C20—C19	120.2 (4)
C10—N5—Ca1	118.5 (3)	C22—C21—C20	119.2 (5)
C19—N6—C18	118.8 (4)	C22—C21—H21A	120.4
C19—N6—Ca1	119.4 (3)	C20—C21—H21A	120.4
C18—N6—Ca1	120.6 (3)	C23—C22—C21	118.8 (4)
C24—N7—C20	117.7 (4)	C23—C22—H22A	120.6
C24—N7—Ca1	125.7 (3)	C21—C22—H22A	120.6
C20—N7—Ca1	115.7 (3)	C22—C23—C24	118.6 (4)
N4—C1—C2	111.6 (4)	C22—C23—H23A	120.7
N4—C1—H1A	109.3	C24—C23—H23A	120.7
C2—C1—H1A	109.3	N7—C24—C23	123.5 (4)
N4—C1—H1B	109.3	N7—C24—H24A	118.3
C2—C1—H1B	109.3	C23—C24—H24A	118.3
H1A—C1—H1B	108.0	C25—O2—Ca1	135.3 (3)
N3—C2—C1	107.2 (4)	C25—O2—H2	112.3
N3—C2—H2A	110.3	Ca1—O2—H2	112.4
C1—C2—H2A	110.3	O2—C25—H25A	109.5
N3—C2—H2B	110.3	O2—C25—H25B	109.5
C1—C2—H2B	110.3	H25A—C25—H25B	109.5
H2A—C2—H2B	108.5	O2—C25—H25C	109.5
N3—C3—C4	121.3 (4)	H25A—C25—H25C	109.5
N3—C3—H3A	119.3	H25B—C25—H25C	109.5
C4—C3—H3A	119.3	O13—Cl1—O12	107.9 (3)
N1—C4—C5	122.6 (5)	O13—Cl1—O14	107.4 (3)
N1—C4—C3	117.7 (4)	O12—Cl1—O14	111.2 (3)
C5—C4—C3	119.7 (4)	O13—Cl1—O11	109.6 (3)
C6—C5—C4	118.8 (5)	O12—Cl1—O11	110.6 (2)
C6—C5—H5A	120.6	O14—Cl1—O11	110.2 (3)
C4—C5—H5A	120.6	O24—Cl2—O21	116.5 (5)
C7—C6—C5	119.3 (4)	O24—Cl2—O22	113.9 (5)
C7—C6—H6A	120.3	O21—Cl2—O22	117.0 (4)
C5—C6—H6A	120.3	O24—Cl2—O23	92.7 (8)
C6—C7—C8	118.4 (5)	O21—Cl2—O23	107.3 (5)
C6—C7—H7A	120.8	O22—Cl2—O23	105.5 (4)
C8—C7—H7A	120.8	C26—O1—H1	112.0
N1—C8—C7	124.1 (5)	O1—C26—H26A	109.5
N1—C8—H8A	117.9	O1—C26—H26B	109.5
C7—C8—H8A	117.9	H26A—C26—H26B	109.5
N4—C9—C10	113.1 (4)	O1—C26—H26C	109.5
N4—C9—H9A	109.0	H26A—C26—H26C	109.5
C10—C9—H9A	109.0	H26B—C26—H26C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O23^i	0.82	2.09	2.899 (9)	168

Symmetry code: (i) −x, −y+1, z+1/2.