Tetra­kis(μ-benzoato-κ²O:O′)bis­(4-ethyl­pyridine-κN)dicopper(II)

The bis­(4-ethyl­pyridine) adduct of dicopper(II) tetra­benzoate, [Cu₂(C₇H₅O₂)₄(C₇H₉N)₂], has centrosymmetrically related square-pyramidal Cu atoms bridged by four benzoate ions; the heterocyclic ligands that occupy the apical sites are disordered.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.045
• wR factor = 0.145
• Data-to-parameter ratio = 22.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       5.34 Ratio

Author Response: 'Disordered structure: please see _publ_section_exptl_refinement'

Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.66 Ratio
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C16
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       C16'
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C20
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C20'
PLAT432_ALERT_2_B Short Inter X...Y Contact  C19    ..  C19     ..       3.04 Ang.

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT213_ALERT_2_C Atom C21     has ADP max/min Ratio .............       3.30 oblat
PLAT213_ALERT_2_C Atom C21'    has ADP max/min Ratio .............       3.30 oblat
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C12
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C15'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N1'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C17'
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.03
PLAT301_ALERT_3_C Main Residue  Disorder .........................      23.00 Perc.
PLAT411_ALERT_2_C Short Inter H...H Contact  H4     ..  H15'    ..       2.11 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C11    ..  C16'    ..       3.15 Ang.

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

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  19 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999); software used to prepare material for publication: SHELXL97.

Tetrakis(µ-benzoato-κ²O:O')bis(4-ethylpyridine-κN)dicopper(II)

Crystal data

[Cu2(C7H5O2)4(C7H9N)2]	F(000) = 852
Mr = 825.82	Dx = 1.395 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.2298 (2) Å	Cell parameters from 7668 reflections
b = 10.9739 (2) Å	θ = 2.2–27.1°
c = 17.5785 (4) Å	µ = 1.14 mm^−1
β = 94.737 (1)°	T = 293 K
V = 1966.64 (7) Å^3	Rod, green blue
Z = 2	0.44 × 0.34 × 0.22 mm

Data collection

Bruker SMART area-detector diffractometer	4868 independent reflections
Radiation source: fine-focus sealed tube	3765 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2004)	h = −12→13
Tmin = 0.635, Tmax = 0.788	k = −14→14
16781 measured reflections	l = −23→23

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0848P)^2 + 0.8035P] where P = (Fo^2 + 2Fc^2)/3
4868 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.53 e Å^−3
54 restraints	Δρmin = −0.43 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

8.8901 (0.0038) x + 4.7281 (0.0071) y + 2.9986 (0.0134) z = 7.9681 (0.0023)

* 0.1746 (0.0008) Cu1 * -0.0428 (0.0010) O1 * -0.0443 (0.0010) O3 * -0.0427 (0.0010) O2_$1 * -0.0448 (0.0010) O4_$1

Rms deviation of fitted atoms = 0.0873

- 2.8692 (0.0290) x + 6.0614 (0.0355) y - 13.3451 (0.0519) z = 1.0359 (0.0301)

* 0.0011 (0.0011) N1_a * 0.0004 (0.0004) C15_a * -0.0010 (0.0011) C16_a * -0.0017 (0.0018) C17_a * -0.0011 (0.0011) C18_a * 0.0003 (0.0004) C19_a * 0.0020 (0.0021) C20_a

Rms deviation of fitted atoms = 0.0012

- 5.8421 (0.0469) x + 8.8498 (0.0332) y - 1.8571 (0.1475) z = 0.8288 (0.0627)

Angle to previous plane (with approximate e.s.d.) = 43.45 (0.59)

* 0.0024 (0.0012) N1'_b * 0.0007 (0.0004) C15'_b * -0.0024 (0.0012) C16'_b * -0.0039 (0.0020) C17'_b * -0.0022 (0.0012) C18'_b * 0.0009 (0.0005) C19'_b * 0.0045 (0.0023) C20'_b

Rms deviation of fitted atoms = 0.0027

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	0.61628 (3)	0.54921 (3)	0.022371 (16)	0.04524 (13)
O1	0.6581 (2)	0.39227 (18)	0.07328 (12)	0.0617 (5)
O2	0.46432 (19)	0.31011 (18)	0.03293 (12)	0.0598 (5)
O3	0.5322 (2)	0.6035 (2)	0.11301 (11)	0.0620 (5)
O4	0.3378 (2)	0.5218 (2)	0.07494 (12)	0.0641 (5)
C1	0.5766 (3)	0.3070 (2)	0.06876 (14)	0.0498 (6)
C2	0.6135 (2)	0.19091 (15)	0.10865 (12)	0.0569 (6)
C3	0.7165 (2)	0.18829 (18)	0.16539 (15)	0.0906 (12)
H3	0.7639	0.2589	0.1777	0.109*
C4	0.7486 (3)	0.0802 (2)	0.20369 (18)	0.123 (2)
H4	0.8175	0.0784	0.2417	0.147*
C5	0.6778 (3)	−0.02531 (19)	0.18524 (19)	0.128 (2)
H5	0.6993	−0.0976	0.2109	0.153*
C6	0.5748 (3)	−0.02270 (17)	0.12850 (18)	0.1052 (16)
H6	0.5274	−0.0933	0.1162	0.126*
C7	0.5427 (2)	0.08541 (19)	0.09020 (14)	0.0711 (9)
H7	0.4738	0.0872	0.0522	0.085*
C8	0.4134 (3)	0.5821 (2)	0.12057 (15)	0.0536 (6)
C9	0.3563 (2)	0.6346 (2)	0.18848 (11)	0.0635 (8)
C10	0.2279 (2)	0.6071 (3)	0.20261 (16)	0.1014 (15)
H10	0.1788	0.5536	0.1707	0.122*
C11	0.1729 (3)	0.6594 (4)	0.2645 (2)	0.152 (3)
H11	0.0870	0.6410	0.2740	0.183*
C12	0.2462 (3)	0.7393 (4)	0.31227 (18)	0.151 (3)
H12	0.2094	0.7743	0.3537	0.182*
C13	0.3746 (3)	0.7668 (3)	0.29813 (15)	0.1092 (16)
H13	0.4237	0.8203	0.3301	0.131*
C14	0.4297 (2)	0.7145 (2)	0.23624 (14)	0.0759 (9)
H14	0.5156	0.7329	0.2268	0.091*
N1	0.8027 (3)	0.6437 (3)	0.0421 (3)	0.0566 (8)	0.676 (5)
C15	0.8089 (4)	0.7473 (5)	0.0878 (4)	0.125 (3)	0.676 (5)
H15	0.7369	0.7700	0.1136	0.150*	0.676 (5)
C16	0.9228 (5)	0.8168 (4)	0.0951 (4)	0.153 (4)	0.676 (5)
H16	0.9270	0.8861	0.1257	0.184*	0.676 (5)
C17	1.0305 (4)	0.7829 (4)	0.0566 (3)	0.101 (3)	0.676 (5)
C18	1.0242 (4)	0.6794 (5)	0.0108 (3)	0.101 (2)	0.676 (5)
H18	1.0962	0.6567	−0.0149	0.121*	0.676 (5)
C19	0.9103 (4)	0.6098 (4)	0.0036 (3)	0.088 (2)	0.676 (5)
H19	0.9062	0.5406	−0.0270	0.106*	0.676 (5)
C20	1.1626 (8)	0.8555 (8)	0.0608 (6)	0.136 (4)	0.676 (5)
H20A	1.2277	0.8076	0.0909	0.163*	0.676 (5)
H20B	1.1906	0.8601	0.0095	0.163*	0.676 (5)
C21	1.1657 (17)	0.9637 (12)	0.0883 (14)	0.264 (10)	0.676 (5)
H21A	1.2533	0.9952	0.0890	0.396*	0.676 (5)
H21B	1.1389	0.9619	0.1393	0.396*	0.676 (5)
H21C	1.1072	1.0149	0.0571	0.396*	0.676 (5)
N1'	0.8029 (8)	0.6355 (7)	0.0548 (7)	0.0566 (8)	0.324 (5)
C15'	0.8353 (10)	0.6724 (11)	0.1297 (6)	0.125 (3)	0.324 (5)
H15'	0.7846	0.6471	0.1683	0.150*	0.324 (5)
C16'	0.9435 (11)	0.7470 (11)	0.1468 (6)	0.153 (4)	0.324 (5)
H16'	0.9652	0.7717	0.1969	0.184*	0.324 (5)
C17'	1.0193 (8)	0.7848 (8)	0.0891 (7)	0.101 (3)	0.324 (5)
C18'	0.9869 (9)	0.7479 (11)	0.0143 (6)	0.101 (2)	0.324 (5)
H18'	1.0377	0.7732	−0.0244	0.121*	0.324 (5)
C19'	0.8787 (10)	0.6732 (11)	−0.0029 (6)	0.088 (2)	0.324 (5)
H19'	0.8571	0.6486	−0.0529	0.106*	0.324 (5)
C20'	1.1353 (14)	0.8672 (15)	0.1125 (12)	0.136 (4)	0.324 (5)
H20C	1.1064	0.9338	0.1433	0.163*	0.324 (5)
H20D	1.2010	0.8213	0.1433	0.163*	0.324 (5)
C21'	1.193 (4)	0.917 (3)	0.046 (2)	0.264 (10)	0.324 (5)
H21D	1.2754	0.9551	0.0620	0.396*	0.324 (5)
H21E	1.1349	0.9752	0.0211	0.396*	0.324 (5)
H21F	1.2084	0.8516	0.0111	0.396*	0.324 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.04344 (19)	0.0467 (2)	0.04587 (19)	−0.00618 (12)	0.00525 (12)	−0.00030 (12)
O1	0.0578 (11)	0.0505 (11)	0.0751 (13)	−0.0062 (9)	−0.0062 (10)	0.0098 (9)
O2	0.0564 (11)	0.0541 (11)	0.0674 (12)	−0.0069 (9)	−0.0044 (9)	0.0115 (9)
O3	0.0607 (12)	0.0757 (13)	0.0507 (10)	−0.0040 (11)	0.0104 (9)	−0.0096 (10)
O4	0.0644 (12)	0.0716 (13)	0.0588 (11)	−0.0092 (10)	0.0191 (10)	−0.0134 (10)
C1	0.0562 (15)	0.0490 (13)	0.0449 (13)	−0.0015 (12)	0.0077 (11)	0.0013 (10)
C2	0.0634 (16)	0.0497 (14)	0.0568 (15)	−0.0052 (13)	−0.0005 (12)	0.0064 (12)
C3	0.101 (3)	0.063 (2)	0.100 (3)	−0.0120 (19)	−0.040 (2)	0.0126 (19)
C4	0.138 (4)	0.080 (3)	0.136 (4)	−0.015 (3)	−0.071 (4)	0.033 (3)
C5	0.152 (5)	0.071 (3)	0.148 (5)	−0.018 (3)	−0.057 (4)	0.047 (3)
C6	0.115 (4)	0.064 (2)	0.129 (4)	−0.024 (2)	−0.033 (3)	0.029 (2)
C7	0.076 (2)	0.0565 (17)	0.078 (2)	−0.0102 (16)	−0.0071 (17)	0.0111 (15)
C8	0.0666 (17)	0.0484 (13)	0.0477 (13)	0.0027 (13)	0.0160 (12)	0.0036 (11)
C9	0.083 (2)	0.0519 (15)	0.0588 (16)	0.0004 (15)	0.0260 (15)	−0.0037 (13)
C10	0.105 (3)	0.108 (3)	0.099 (3)	−0.027 (3)	0.056 (3)	−0.035 (3)
C11	0.147 (5)	0.171 (6)	0.155 (5)	−0.041 (4)	0.105 (4)	−0.074 (5)
C12	0.160 (5)	0.162 (5)	0.145 (5)	−0.018 (5)	0.090 (4)	−0.080 (4)
C13	0.140 (4)	0.100 (3)	0.092 (3)	−0.001 (3)	0.033 (3)	−0.046 (3)
C14	0.094 (3)	0.0663 (19)	0.0691 (19)	0.0035 (18)	0.0193 (18)	−0.0138 (16)
N1	0.0497 (12)	0.0589 (14)	0.060 (2)	−0.0106 (11)	−0.0023 (12)	0.0074 (14)
C15	0.085 (4)	0.095 (5)	0.197 (9)	−0.041 (4)	0.026 (5)	−0.043 (5)
C16	0.101 (5)	0.100 (6)	0.256 (13)	−0.045 (5)	0.000 (7)	−0.045 (7)
C17	0.069 (3)	0.099 (3)	0.130 (7)	−0.031 (3)	−0.018 (4)	0.029 (4)
C18	0.051 (3)	0.134 (7)	0.118 (4)	−0.019 (3)	0.007 (3)	0.024 (5)
C19	0.052 (3)	0.116 (6)	0.097 (3)	−0.019 (3)	0.006 (2)	0.005 (4)
C20	0.099 (5)	0.122 (5)	0.184 (10)	−0.055 (4)	0.001 (6)	0.031 (8)
C21	0.191 (12)	0.159 (14)	0.44 (3)	−0.126 (12)	−0.014 (14)	−0.046 (13)
N1'	0.0497 (12)	0.0589 (14)	0.060 (2)	−0.0106 (11)	−0.0023 (12)	0.0074 (14)
C15'	0.085 (4)	0.095 (5)	0.197 (9)	−0.041 (4)	0.026 (5)	−0.043 (5)
C16'	0.101 (5)	0.100 (6)	0.256 (13)	−0.045 (5)	0.000 (7)	−0.045 (7)
C17'	0.069 (3)	0.099 (3)	0.130 (7)	−0.031 (3)	−0.018 (4)	0.029 (4)
C18'	0.051 (3)	0.134 (7)	0.118 (4)	−0.019 (3)	0.007 (3)	0.024 (5)
C19'	0.052 (3)	0.116 (6)	0.097 (3)	−0.019 (3)	0.006 (2)	0.005 (4)
C20'	0.099 (5)	0.122 (5)	0.184 (10)	−0.055 (4)	0.001 (6)	0.031 (8)
C21'	0.191 (12)	0.159 (14)	0.44 (3)	−0.126 (12)	−0.014 (14)	−0.046 (13)

Geometric parameters (Å, º)

Cu1—O3	1.9644 (19)	C14—H14	0.9300
Cu1—O2^i	1.9686 (19)	N1—C15	1.3900
Cu1—O4^i	1.971 (2)	N1—C19	1.3900
Cu1—O1	1.972 (2)	C15—C16	1.3900
Cu1—N1'	2.165 (7)	C15—H15	0.9300
Cu1—N1	2.173 (3)	C16—C17	1.3900
Cu1—Cu1^i	2.6714 (6)	C16—H16	0.9300
O1—C1	1.252 (3)	C17—C18	1.3900
O2—C1	1.264 (3)	C17—C20	1.565 (7)
O2—Cu1^i	1.9686 (19)	C18—C19	1.3900
O3—C8	1.256 (3)	C18—H18	0.9300
O4—C8	1.255 (4)	C19—H19	0.9300
O4—Cu1^i	1.971 (2)	C20—C21	1.281 (14)
C1—C2	1.488 (3)	C20—H20A	0.9700
C2—C3	1.3900	C20—H20B	0.9700
C2—C7	1.3900	C21—H21A	0.9600
C3—C4	1.3900	C21—H21B	0.9600
C3—H3	0.9300	C21—H21C	0.9600
C4—C5	1.3900	N1'—C15'	1.3900
C4—H4	0.9300	N1'—C19'	1.3900
C5—C6	1.3900	C15'—C16'	1.3900
C5—H5	0.9300	C15'—H15'	0.9300
C6—C7	1.3900	C16'—C17'	1.3900
C6—H6	0.9300	C16'—H16'	0.9300
C7—H7	0.9300	C17'—C18'	1.3900
C8—C9	1.488 (3)	C17'—C20'	1.521 (14)
C9—C10	1.3900	C18'—C19'	1.3900
C9—C14	1.3900	C18'—H18'	0.9300
C10—C11	1.3900	C19'—H19'	0.9300
C10—H10	0.9300	C20'—C21'	1.46 (2)
C11—C12	1.3900	C20'—H20C	0.9700
C11—H11	0.9300	C20'—H20D	0.9700
C12—C13	1.3900	C21'—H21D	0.9600
C12—H12	0.9300	C21'—H21E	0.9600
C13—C14	1.3900	C21'—H21F	0.9600
C13—H13	0.9300
O3—Cu1—O2^i	88.24 (9)	C13—C14—C9	120.0
O3—Cu1—O4^i	167.21 (9)	C13—C14—H14	120.0
O2^i—Cu1—O4^i	90.09 (10)	C9—C14—H14	120.0
O3—Cu1—O1	89.42 (10)	C15—N1—C19	120.0
O2^i—Cu1—O1	167.30 (8)	C15—N1—Cu1	118.7 (2)
O4^i—Cu1—O1	89.44 (10)	C19—N1—Cu1	121.0 (2)
O3—Cu1—N1'	95.1 (3)	N1—C15—C16	120.0
O2^i—Cu1—N1'	96.4 (3)	N1—C15—H15	120.0
O4^i—Cu1—N1'	97.7 (3)	C16—C15—H15	120.0
O1—Cu1—N1'	96.2 (3)	C17—C16—C15	120.0
O3—Cu1—N1	99.37 (14)	C17—C16—H16	120.0
O2^i—Cu1—N1	91.76 (13)	C15—C16—H16	120.0
O4^i—Cu1—N1	93.35 (14)	C18—C17—C16	120.0
O1—Cu1—N1	100.94 (13)	C18—C17—C20	116.2 (5)
N1'—Cu1—N1	6.4 (4)	C16—C17—C20	123.8 (5)
O3—Cu1—Cu1^i	85.56 (6)	C19—C18—C17	120.0
O2^i—Cu1—Cu1^i	81.09 (6)	C19—C18—H18	120.0
O4^i—Cu1—Cu1^i	81.66 (7)	C17—C18—H18	120.0
O1—Cu1—Cu1^i	86.28 (6)	C18—C19—N1	120.0
N1'—Cu1—Cu1^i	177.4 (3)	C18—C19—H19	120.0
N1—Cu1—Cu1^i	171.23 (13)	N1—C19—H19	120.0
C1—O1—Cu1	120.39 (18)	C21—C20—C17	118.9 (10)
C1—O2—Cu1^i	126.42 (18)	C21—C20—H20A	107.6
C8—O3—Cu1	121.42 (19)	C17—C20—H20A	107.6
C8—O4—Cu1^i	125.76 (19)	C21—C20—H20B	107.6
O1—C1—O2	125.8 (3)	C17—C20—H20B	107.6
O1—C1—C2	117.9 (2)	H20A—C20—H20B	107.0
O2—C1—C2	116.3 (2)	C20—C21—H21A	109.5
C3—C2—C7	120.0	C20—C21—H21B	109.5
C3—C2—C1	120.25 (16)	H21A—C21—H21B	109.5
C7—C2—C1	119.73 (16)	C20—C21—H21C	109.5
C2—C3—C4	120.0	H21A—C21—H21C	109.5
C2—C3—H3	120.0	H21B—C21—H21C	109.5
C4—C3—H3	120.0	C15'—N1'—C19'	120.0
C5—C4—C3	120.0	C15'—N1'—Cu1	120.9 (6)
C5—C4—H4	120.0	C19'—N1'—Cu1	118.1 (6)
C3—C4—H4	120.0	C16'—C15'—N1'	120.0
C6—C5—C4	120.0	C16'—C15'—H15'	120.0
C6—C5—H5	120.0	N1'—C15'—H15'	120.0
C4—C5—H5	120.0	C15'—C16'—C17'	120.0
C5—C6—C7	120.0	C15'—C16'—H16'	120.0
C5—C6—H6	120.0	C17'—C16'—H16'	120.0
C7—C6—H6	120.0	C18'—C17'—C16'	120.0
C6—C7—C2	120.0	C18'—C17'—C20'	123.3 (9)
C6—C7—H7	120.0	C16'—C17'—C20'	116.7 (9)
C2—C7—H7	120.0	C19'—C18'—C17'	120.0
O4—C8—O3	125.5 (3)	C19'—C18'—H18'	120.0
O4—C8—C9	117.1 (3)	C17'—C18'—H18'	120.0
O3—C8—C9	117.4 (3)	C18'—C19'—N1'	120.0
C10—C9—C14	120.0	C18'—C19'—H19'	120.0
C10—C9—C8	119.89 (18)	N1'—C19'—H19'	120.0
C14—C9—C8	120.08 (18)	C21'—C20'—C17'	111.4 (15)
C11—C10—C9	120.0	C21'—C20'—H20C	109.3
C11—C10—H10	120.0	C17'—C20'—H20C	109.3
C9—C10—H10	120.0	C21'—C20'—H20D	109.3
C12—C11—C10	120.0	C17'—C20'—H20D	109.3
C12—C11—H11	120.0	H20C—C20'—H20D	108.0
C10—C11—H11	120.0	C20'—C21'—H21D	109.5
C11—C12—C13	120.0	C20'—C21'—H21E	109.5
C11—C12—H12	120.0	H21D—C21'—H21E	109.5
C13—C12—H12	120.0	C20'—C21'—H21F	109.5
C14—C13—C12	120.0	H21D—C21'—H21F	109.5
C14—C13—H13	120.0	H21E—C21'—H21F	109.5
C12—C13—H13	120.0

Symmetry code: (i) −x+1, −y+1, −z.