Variable-temperature X-ray crystallographic studies: a complementary tool for charge-density investigation of soft (organometallic) bonds

Comparative X-ray diffraction studies at different temperatures are used to complement the information usually extracted from `single-point' charge-density studies. The response of soft bonds against (temperature driven) changes of the crystalline environment might be indicative of some intramolecular mode associated with an incipient bonding. This is in fact confirmed for the anion [FeCo(CO)₈]^- in the [(Ph₃P)₂N]⁺ salt. In contrast, the [Cr₂H(CO)₁₀]^- anion, whose conformation is known to strongly depend on the counterion, is actually insensitive to T variations in the [K(C₁₈H₃₆N₂O₆)]⁺ salt.

Computing details

Program(s) used to refine structure: Koritsanszky et al., (2003); molecular graphics: Koritsanszky et al., (2003); software used to prepare material for publication: Koritsanszky et al., (2003).

Figures

(I)

Crystal data

C10HO10Cr2·C18H36O6N2K	F(000) = 1656.0
Mr = 800.69	Dx = 1.489 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
a = 10.458 Å	Cell parameters from 1024 reflections
b = 14.4168 Å	θ = 47.5–1.5°
c = 23.8824 Å	µ = 0.8 mm^−1
β = 97.264°	T = 28 K
V = 3571.9 (2) Å^3	Ellipsoidal, yellow
Z = 4	0.3 × 0.25 × 0.2 mm

Data collection

SMART CCD diffractometer	20964 reflections with > 3σ(F)
Graphite monochromator	Rint = 0.039
ω scan	θmax = 48.4°, θmin = 1°
Absorption correction: empirical (using intensity measurements) ?	h = −20→20
Tmin = 0.890, Tmax = 0.903	k = −30→30
128749 measured reflections	l = −50→45
30760 independent reflections

Refinement

Refinement on F	0 restraints
Least-squares matrix: full	H parameters constrained
R[F^2 > 2σ(F^2)] = 0.026	w1 = Fo*sqrt(w2) + sqrt(Fo^2w2^2 + sqrt(w2^2)) where w2 = q/[s^2(Fo^2) + (0.00 P)^2 + 0.00 P + 0.00 + 0.00 sin(th)] where P = (0.3333 Fo^2 + 0.6667 Fc^2) q = 1.0
wR(F^2) = 0.021	(Δ/σ)max = 0.0004
S = 1.21	Δρmax = 0.25 e Å^−3
20964 reflections	Δρmin = −0.29 e Å^−3
1354 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
CR(1)	0.163882 (15)	0.002348 (9)	0.236369 (6)	0.005
CR(2)	0.018777 (16)	0.177474 (9)	0.165110 (6)	0.006
K(1)	0.463718 (11)	0.199287 (7)	0.418003 (5)	0.007
O(1)	0.25227 (10)	0.13824 (5)	0.33131 (4)	0.012
O(2)	−0.08392 (11)	−0.04358 (7)	0.28579 (4)	0.015
O(3)	0.10470 (10)	−0.12670 (6)	0.13540 (4)	0.013
O(4)	0.39554 (11)	0.05463 (6)	0.17740 (4)	0.014
O(5)	0.30045 (10)	−0.15045 (5)	0.30582 (4)	0.012
O(6)	−0.25963 (11)	0.12170 (6)	0.17223 (4)	0.013
O(7)	0.01681 (11)	0.05850 (6)	0.05945 (4)	0.013
O(8)	0.28653 (11)	0.25370 (7)	0.15527 (4)	0.014
O(9)	0.02673 (13)	0.26575 (7)	0.28184 (4)	0.018
O(10)	−0.07227 (11)	0.34778 (6)	0.09914 (4)	0.015
O(11)	0.28589 (8)	0.09211 (5)	0.47315 (3)	0.008
O(12)	0.44339 (8)	0.00284 (5)	0.40244 (3)	0.008
O(13)	0.31318 (9)	0.34086 (5)	0.36292 (3)	0.009
O(14)	0.52836 (9)	0.26683 (5)	0.31530 (3)	0.009
O(15)	0.55083 (8)	0.32676 (5)	0.50759 (3)	0.009
O(16)	0.72719 (8)	0.20507 (5)	0.46498 (3)	0.008
N(1)	0.27320 (7)	0.30195 (4)	0.47981 (3)	0.008
N(2)	0.66178 (7)	0.09463 (4)	0.36200 (3)	0.007
C(1)	0.21617 (7)	0.08852 (4)	0.29498 (3)	0.008
C(2)	0.01016 (7)	−0.02691 (4)	0.26770 (3)	0.009
C(3)	0.12290 (7)	−0.07910 (4)	0.17424 (3)	0.009
C(4)	0.30793 (7)	0.03661 (4)	0.20005 (3)	0.009
C(5)	0.25018 (7)	−0.09114 (4)	0.27862 (3)	0.009
C(6)	−0.15434 (7)	0.14176 (4)	0.16995 (3)	0.009
C(7)	0.01890 (7)	0.10409 (4)	0.09922 (3)	0.009
C(8)	0.18804 (7)	0.22108 (4)	0.16012 (3)	0.009
C(9)	0.02394 (7)	0.23370 (4)	0.23774 (3)	0.011
C(10)	−0.03865 (7)	0.28233 (4)	0.12529 (3)	0.009
C(11)	0.20823 (8)	0.23293 (5)	0.51164 (3)	0.009
C(12)	0.17313 (7)	0.14346 (4)	0.47989 (3)	0.009
C(13)	0.25202 (7)	0.00552 (4)	0.44639 (3)	0.008
C(14)	0.37237 (8)	−0.04784 (4)	0.43911 (3)	0.008
C(15)	0.54825 (7)	−0.04995 (4)	0.38674 (3)	0.008
C(16)	0.60983 (7)	0.00367 (4)	0.34255 (3)	0.008
C(17)	0.17932 (8)	0.34652 (5)	0.43697 (3)	0.01
C(18)	0.24067 (8)	0.40164 (5)	0.39328 (3)	0.01
C(19)	0.37495 (9)	0.38876 (5)	0.32186 (3)	0.011
C(20)	0.42821 (8)	0.31885 (5)	0.28409 (3)	0.011
C(21)	0.57202 (8)	0.19486 (5)	0.28134 (3)	0.01
C(22)	0.69026 (8)	0.14948 (5)	0.31300 (3)	0.009
C(23)	0.33596 (8)	0.37157 (5)	0.51924 (3)	0.01
C(24)	0.46538 (8)	0.34034 (5)	0.54886 (3)	0.011
C(25)	0.68004 (7)	0.31747 (5)	0.53312 (3)	0.009
C(26)	0.76443 (8)	0.29307 (5)	0.48870 (3)	0.009
C(27)	0.82393 (7)	0.16969 (5)	0.43401 (3)	0.009
C(28)	0.77754 (8)	0.08193 (4)	0.40290 (3)	0.009
H(1)	0.0476	0.0728	0.1997	0.04
H(2)	0.1188	0.2613	0.5253	0.026
H(3)	0.2724	0.2151	0.5499	0.023
H(4)	0.118	0.1562	0.4383	0.024
H(5)	0.1105	0.1018	0.5044	0.025
H(6)	0.1949	0.0168	0.4052	0.022
H(7)	0.193	−0.0358	0.4725	0.023
H(8)	0.3441	−0.1156	0.4207	0.027
H(9)	0.4314	−0.0592	0.4802	0.023
H(10)	0.5125	−0.116	0.368	0.022
H(11)	0.6156	−0.0657	0.4243	0.022
H(12)	0.536	0.0151	0.3065	0.021
H(13)	0.6855	−0.0403	0.3276	0.024
H(14)	0.1204	0.2926	0.4139	0.023
H(15)	0.1143	0.3931	0.4565	0.026
H(16)	0.1645	0.4343	0.3643	0.026
H(17)	0.3031	0.4573	0.4124	0.028
H(18)	0.4517	0.433	0.3424	0.03
H(19)	0.3047	0.433	0.2957	0.028
H(20)	0.3501	0.2725	0.2655	0.025
H(21)	0.4657	0.3554	0.2488	0.029
H(22)	0.5965	0.2241	0.2415	0.026
H(23)	0.4941	0.1457	0.2704	0.023
H(24)	0.7366	0.1057	0.2833	0.025
H(25)	0.7573	0.2046	0.3275	0.025
H(26)	0.3534	0.4343	0.4955	0.026
H(27)	0.2738	0.3917	0.5518	0.027
H(28)	0.4585	0.276	0.5729	0.026
H(29)	0.5037	0.3936	0.5793	0.027
H(30)	0.7143	0.383	0.5534	0.024
H(31)	0.6878	0.2636	0.5661	0.024
H(32)	0.7566	0.3461	0.4552	0.026
H(33)	0.8652	0.2908	0.5087	0.026
H(34)	0.8515	0.2231	0.4052	0.025
H(35)	0.9099	0.1532	0.4634	0.027
H(36)	0.8576	0.0536	0.3826	0.027
H(37)	0.7553	0.0304	0.434	0.023
DUM0	0	0	0	0	0

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
CR(1)	0.00576 (5)	0.00467 (3)	0.00527 (5)	0.00022 (4)	0.00060 (4)	−0.00013 (3)
CR(2)	0.00672 (6)	0.00544 (4)	0.00508 (5)	0.00085 (4)	0.00025 (4)	0.00020 (4)
K(1)	0.00617 (5)	0.00678 (4)	0.00675 (4)	0.00022 (3)	0.00053 (3)	−0.00002 (3)
O(1)	0.0159 (4)	0.0094 (2)	0.0093 (3)	0.0002 (3)	−0.0024 (3)	−0.0033 (2)
O(2)	0.0097 (4)	0.0178 (3)	0.0165 (4)	−0.0003 (3)	0.0062 (3)	0.0019 (3)
O(3)	0.0158 (4)	0.0125 (3)	0.0101 (3)	−0.0022 (3)	0.0019 (3)	−0.0054 (2)
O(4)	0.0108 (4)	0.0142 (3)	0.0176 (4)	−0.0009 (3)	0.0076 (3)	0.0002 (3)
O(5)	0.0144 (4)	0.0086 (2)	0.0136 (3)	0.0036 (3)	−0.0010 (3)	0.0031 (2)
O(6)	0.0095 (4)	0.0153 (3)	0.0130 (3)	−0.0010 (3)	0.0032 (3)	0.0000 (2)
O(7)	0.0174 (4)	0.0123 (3)	0.0087 (3)	−0.0011 (3)	0.0027 (3)	−0.0034 (2)
O(8)	0.0107 (4)	0.0168 (3)	0.0128 (4)	−0.0053 (3)	0.0008 (3)	0.0005 (3)
O(9)	0.0267 (5)	0.0176 (3)	0.0083 (4)	0.0097 (3)	−0.0013 (3)	−0.0053 (3)
O(10)	0.0179 (4)	0.0097 (3)	0.0160 (4)	0.0032 (3)	−0.0019 (3)	0.0048 (3)
O(11)	0.0060 (3)	0.0074 (2)	0.0099 (3)	−0.0001 (2)	0.0015 (2)	−0.00129 (19)
O(12)	0.0085 (3)	0.00686 (19)	0.0099 (3)	0.0009 (2)	0.0033 (2)	0.00114 (19)
O(13)	0.0095 (3)	0.00718 (19)	0.0098 (3)	0.0010 (2)	0.0031 (2)	0.00137 (19)
O(14)	0.0099 (3)	0.0088 (2)	0.0078 (3)	0.0022 (2)	0.0009 (2)	0.00028 (19)
O(15)	0.0070 (3)	0.0131 (2)	0.0074 (3)	0.0015 (2)	0.0003 (2)	−0.0016 (2)
O(16)	0.0059 (3)	0.0090 (2)	0.0096 (3)	−0.0011 (2)	0.0016 (2)	−0.00277 (19)
N(1)	0.0073 (3)	0.00826 (18)	0.0082 (2)	0.00095 (19)	0.00050 (18)	−0.00026 (17)
N(2)	0.0076 (3)	0.00681 (17)	0.0065 (2)	−0.00005 (18)	0.00092 (18)	0.00018 (15)
C(1)	0.0096 (3)	0.00729 (18)	0.0076 (2)	−0.00011 (18)	−0.00010 (18)	−0.00070 (16)
C(2)	0.0084 (3)	0.00920 (19)	0.0098 (2)	0.00065 (19)	0.0028 (2)	0.00071 (17)
C(3)	0.0092 (3)	0.00851 (18)	0.0080 (2)	−0.00054 (19)	0.00082 (18)	−0.00144 (17)
C(4)	0.0082 (3)	0.00927 (19)	0.0102 (2)	−0.00050 (19)	0.0021 (2)	−0.00052 (17)
C(5)	0.0088 (3)	0.00683 (18)	0.0098 (2)	0.00110 (18)	0.00040 (19)	0.00054 (17)
C(6)	0.0092 (3)	0.00987 (19)	0.0079 (2)	0.00100 (19)	0.00133 (19)	0.00060 (16)
C(7)	0.0095 (3)	0.00861 (18)	0.0075 (2)	−0.00037 (18)	0.00159 (18)	−0.00094 (17)
C(8)	0.0097 (3)	0.00948 (19)	0.0085 (2)	−0.0009 (2)	0.00031 (19)	0.00004 (16)
C(9)	0.0146 (3)	0.0105 (2)	0.0080 (3)	0.0038 (2)	−0.0002 (2)	−0.00177 (18)
C(10)	0.0114 (3)	0.00752 (18)	0.0091 (2)	0.00128 (19)	−0.00039 (19)	0.00116 (17)
C(11)	0.0097 (3)	0.0099 (2)	0.0082 (3)	0.0014 (2)	0.0020 (2)	−0.00029 (18)
C(12)	0.0066 (3)	0.0093 (2)	0.0104 (3)	−0.0001 (2)	0.0013 (2)	0.00013 (18)
C(13)	0.0075 (3)	0.00780 (19)	0.0091 (2)	−0.0016 (2)	0.0017 (2)	−0.00049 (18)
C(14)	0.0094 (3)	0.00716 (19)	0.0089 (3)	−0.0002 (2)	0.0024 (2)	0.00065 (17)
C(15)	0.0080 (3)	0.00667 (18)	0.0101 (3)	0.00085 (19)	0.0018 (2)	0.00042 (17)
C(16)	0.0092 (3)	0.00791 (19)	0.0079 (2)	−0.0003 (2)	0.0014 (2)	−0.00087 (18)
C(17)	0.0079 (3)	0.0104 (2)	0.0104 (3)	0.0019 (2)	0.0018 (2)	0.0013 (2)
C(18)	0.0106 (3)	0.0081 (2)	0.0117 (3)	0.0020 (2)	0.0031 (2)	0.00135 (19)
C(19)	0.0131 (3)	0.0084 (2)	0.0127 (3)	0.0021 (2)	0.0043 (2)	0.0029 (2)
C(20)	0.0125 (3)	0.0119 (2)	0.0087 (3)	0.0034 (2)	0.0020 (2)	0.0032 (2)
C(21)	0.0126 (3)	0.0093 (2)	0.0072 (3)	0.0019 (2)	0.0012 (2)	0.00071 (18)
C(22)	0.0098 (3)	0.0096 (2)	0.0092 (3)	0.0010 (2)	0.0031 (2)	0.00179 (19)
C(23)	0.0086 (3)	0.0101 (2)	0.0121 (3)	0.0013 (2)	0.0008 (2)	−0.0034 (2)
C(24)	0.0081 (3)	0.0144 (2)	0.0091 (3)	0.0005 (2)	0.0010 (2)	−0.0031 (2)
C(25)	0.0081 (3)	0.0101 (2)	0.0083 (3)	−0.0003 (2)	−0.0001 (2)	−0.00194 (19)
C(26)	0.0080 (3)	0.0093 (2)	0.0107 (3)	−0.0014 (2)	0.0015 (2)	−0.00199 (19)
C(27)	0.0073 (3)	0.0103 (2)	0.0103 (3)	−0.0007 (2)	0.0014 (2)	−0.00202 (19)
C(28)	0.0079 (3)	0.0086 (2)	0.0094 (3)	0.0010 (2)	0.0010 (2)	−0.00061 (18)
H(1)	0.038	0.03	0.05	0.018	−0.002	0.004
H(2)	0.023	0.028	0.028	0.001	0.01	0.005
H(3)	0.026	0.025	0.017	0.003	−0.002	0.003
H(4)	0.023	0.024	0.024	−0.002	−0.005	0
H(5)	0.022	0.022	0.031	0.004	0.01	−0.002
H(6)	0.021	0.025	0.018	−0.002	−0.002	0
H(7)	0.026	0.02	0.025	0	0.011	−0.004
H(8)	0.028	0.02	0.033	−0.002	0.007	−0.003
H(9)	0.023	0.028	0.018	0.005	−0.001	0.002
H(10)	0.022	0.018	0.026	−0.003	0.006	0
H(11)	0.018	0.027	0.021	0.004	−0.001	0.004
H(12)	0.021	0.023	0.019	0.001	−0.002	−0.001
H(13)	0.024	0.022	0.027	−0.002	0.007	0.004
H(14)	0.022	0.025	0.022	−0.001	−0.004	−0.005
H(15)	0.023	0.03	0.026	0.003	0.006	0.01
H(16)	0.026	0.028	0.025	0.008	0.004	0.009
H(17)	0.031	0.023	0.029	−0.004	0.006	−0.004
H(18)	0.031	0.023	0.036	−0.004	0.011	−0.006
H(19)	0.027	0.028	0.029	0.01	0.007	0.012
H(20)	0.02	0.03	0.024	−0.002	−0.004	0
H(21)	0.034	0.029	0.024	0.01	0.01	0.01
H(22)	0.033	0.027	0.019	0.003	0.006	0.006
H(23)	0.022	0.022	0.025	−0.004	−0.003	0.001
H(24)	0.027	0.026	0.022	0.005	0.009	0.01
H(25)	0.025	0.024	0.025	0.004	0	−0.004
H(26)	0.028	0.019	0.031	0.003	0	−0.003
H(27)	0.023	0.029	0.028	−0.009	0.008	0.001
H(28)	0.023	0.027	0.027	0.005	0.005	0
H(29)	0.022	0.035	0.023	−0.012	0.001	−0.003
H(30)	0.021	0.024	0.027	−0.006	0.002	−0.003
H(31)	0.021	0.027	0.023	0.008	0.003	0.002
H(32)	0.03	0.023	0.025	0.003	0.008	0.001
H(33)	0.021	0.027	0.029	−0.008	0	−0.001
H(34)	0.03	0.019	0.026	−0.002	0.008	−0.005
H(35)	0.017	0.033	0.031	−0.007	−0.004	0.001
H(36)	0.022	0.029	0.029	0.005	0.001	0.006
H(37)	0.028	0.018	0.021	0.006	0	−0.002

Geometric parameters (Å, º)

CR(1)—C(1)	1.8995 (6)	C(13)—H(6)	1.0966 (7)
CR(1)—C(2)	1.9043 (7)	C(13)—H(7)	1.1054 (7)
CR(1)—C(3)	1.8982 (7)	C(14)—H(8)	1.0965 (6)
CR(1)—C(4)	1.8964 (7)	C(14)—H(9)	1.1035 (8)
CR(1)—C(5)	1.8490 (7)	C(15)—C(16)	1.5159 (9)
CR(2)—C(6)	1.8997 (8)	C(15)—H(10)	1.0975 (7)
CR(2)—C(7)	1.8964 (6)	C(15)—H(11)	1.0921 (8)
CR(2)—C(8)	1.8964 (8)	C(16)—H(12)	1.0938 (8)
CR(2)—C(9)	1.9093 (7)	C(16)—H(13)	1.1077 (7)
CR(2)—C(10)	1.8454 (6)	C(17)—C(18)	1.5170 (9)
O(1)—C(1)	1.1516 (10)	C(17)—H(14)	1.0962 (8)
O(2)—C(2)	1.1489 (12)	C(17)—H(15)	1.1005 (7)
O(3)—C(3)	1.1502 (10)	C(18)—H(16)	1.0935 (8)
O(4)—C(4)	1.1511 (12)	C(18)—H(17)	1.0969 (8)
O(5)—C(5)	1.1590 (10)	C(19)—C(20)	1.5056 (10)
O(6)—C(6)	1.1464 (13)	C(19)—H(18)	1.0919 (9)
O(7)—C(7)	1.1528 (10)	C(19)—H(19)	1.1049 (8)
O(8)—C(8)	1.1514 (12)	C(20)—H(20)	1.1042 (9)
O(9)—C(9)	1.1471 (11)	C(20)—H(21)	1.1069 (7)
O(10)—C(10)	1.1612 (10)	C(21)—C(22)	1.5140 (11)
O(11)—C(12)	1.4187 (10)	C(21)—H(22)	1.1001 (7)
O(11)—C(13)	1.4264 (9)	C(21)—H(23)	1.0866 (8)
O(12)—C(14)	1.4203 (9)	C(22)—H(24)	1.1061 (7)
O(12)—C(15)	1.4234 (10)	C(22)—H(25)	1.0870 (8)
O(13)—C(18)	1.4169 (10)	C(23)—C(24)	1.5142 (11)
O(13)—C(19)	1.4199 (10)	C(23)—H(26)	1.0950 (8)
O(14)—C(20)	1.4205 (10)	C(23)—H(27)	1.1132 (7)
O(14)—C(21)	1.4271 (9)	C(24)—H(28)	1.0980 (8)
O(15)—C(24)	1.4251 (10)	C(24)—H(29)	1.0978 (7)
O(15)—C(25)	1.4168 (11)	C(25)—C(26)	1.5050 (10)
O(16)—C(26)	1.4235 (9)	C(25)—H(30)	1.1008 (7)
O(16)—C(27)	1.4213 (10)	C(25)—H(31)	1.1017 (7)
N(1)—C(11)	1.4698 (9)	C(26)—H(32)	1.1022 (7)
N(2)—C(28)	1.4677 (10)	C(26)—H(33)	1.1011 (8)
C(11)—C(12)	1.5176 (9)	C(27)—C(28)	1.5156 (9)
C(11)—H(2)	1.1071 (7)	C(27)—H(34)	1.0953 (7)
C(11)—H(3)	1.0939 (8)	C(27)—H(35)	1.0945 (8)
C(12)—H(4)	1.0990 (8)	C(28)—H(36)	1.0980 (7)
C(12)—H(5)	1.1088 (7)	C(28)—H(37)	1.0960 (7)
C(13)—C(14)	1.5038 (10)
C(1)—CR(1)—C(2)	91.95 (3)	C(15)—C(16)—H(12)	107.76 (6)
C(1)—CR(1)—C(3)	174.93 (3)	C(15)—C(16)—H(13)	108.44 (5)
C(1)—CR(1)—C(4)	89.74 (3)	H(12)—C(16)—H(13)	107.13 (6)
C(1)—CR(1)—C(5)	89.97 (3)	C(18)—C(17)—H(14)	106.58 (6)
C(2)—CR(1)—C(3)	92.97 (3)	C(18)—C(17)—H(15)	108.03 (6)
C(2)—CR(1)—C(4)	175.09 (3)	H(14)—C(17)—H(15)	107.92 (7)
C(2)—CR(1)—C(5)	90.13 (3)	O(13)—C(18)—C(17)	109.16 (6)
C(3)—CR(1)—C(4)	85.27 (3)	O(13)—C(18)—H(16)	109.67 (7)
C(3)—CR(1)—C(5)	91.26 (3)	O(13)—C(18)—H(17)	109.66 (7)
C(4)—CR(1)—C(5)	94.49 (3)	C(17)—C(18)—H(16)	108.86 (7)
C(6)—CR(2)—C(7)	89.99 (3)	C(17)—C(18)—H(17)	112.22 (6)
C(6)—CR(2)—C(8)	176.36 (3)	H(16)—C(18)—H(17)	107.22 (6)
C(6)—CR(2)—C(9)	88.71 (3)	O(13)—C(19)—C(20)	108.87 (6)
C(6)—CR(2)—C(10)	90.16 (3)	O(13)—C(19)—H(18)	110.28 (7)
C(7)—CR(2)—C(8)	91.96 (3)	O(13)—C(19)—H(19)	110.07 (7)
C(7)—CR(2)—C(9)	171.07 (3)	C(20)—C(19)—H(18)	110.71 (7)
C(7)—CR(2)—C(10)	93.65 (3)	C(20)—C(19)—H(19)	108.52 (7)
C(8)—CR(2)—C(9)	89.83 (3)	H(18)—C(19)—H(19)	108.38 (6)
C(8)—CR(2)—C(10)	86.65 (3)	O(14)—C(20)—C(19)	110.07 (7)
C(9)—CR(2)—C(10)	95.19 (3)	O(14)—C(20)—H(20)	110.51 (6)
C(12)—O(11)—C(13)	110.16 (7)	O(14)—C(20)—H(21)	110.02 (7)
C(14)—O(12)—C(15)	111.58 (6)	C(19)—C(20)—H(20)	109.57 (7)
C(18)—O(13)—C(19)	111.86 (6)	C(19)—C(20)—H(21)	109.33 (6)
C(20)—O(14)—C(21)	110.69 (7)	H(20)—C(20)—H(21)	107.29 (6)
C(24)—O(15)—C(25)	111.27 (7)	O(14)—C(21)—C(22)	109.28 (6)
C(26)—O(16)—C(27)	110.49 (7)	O(14)—C(21)—H(22)	109.82 (6)
CR(1)—C(1)—O(1)	177.02 (7)	O(14)—C(21)—H(23)	109.07 (7)
CR(1)—C(2)—O(2)	178.67 (8)	C(22)—C(21)—H(22)	109.44 (7)
CR(1)—C(3)—O(3)	175.90 (7)	C(22)—C(21)—H(23)	112.25 (6)
CR(1)—C(4)—O(4)	177.87 (7)	H(22)—C(21)—H(23)	106.94 (6)
CR(1)—C(5)—O(5)	177.69 (8)	C(21)—C(22)—H(24)	108.82 (6)
CR(2)—C(6)—O(6)	178.65 (7)	C(21)—C(22)—H(25)	107.24 (6)
CR(2)—C(7)—O(7)	178.59 (7)	H(24)—C(22)—H(25)	107.70 (7)
CR(2)—C(8)—O(8)	174.72 (7)	C(24)—C(23)—H(26)	106.85 (7)
CR(2)—C(9)—O(9)	178.62 (8)	C(24)—C(23)—H(27)	108.52 (6)
CR(2)—C(10)—O(10)	178.03 (8)	H(26)—C(23)—H(27)	107.25 (6)
N(1)—C(11)—C(12)	114.55 (6)	O(15)—C(24)—C(23)	108.63 (7)
N(1)—C(11)—H(2)	111.43 (6)	O(15)—C(24)—H(28)	109.50 (6)
N(1)—C(11)—H(3)	108.44 (6)	O(15)—C(24)—H(29)	110.23 (7)
C(12)—C(11)—H(2)	107.53 (6)	C(23)—C(24)—H(28)	112.43 (7)
C(12)—C(11)—H(3)	107.56 (6)	C(23)—C(24)—H(29)	109.35 (6)
H(2)—C(11)—H(3)	107.01 (6)	H(28)—C(24)—H(29)	106.68 (6)
O(11)—C(12)—C(11)	110.38 (6)	O(15)—C(25)—C(26)	109.34 (6)
O(11)—C(12)—H(4)	109.47 (6)	O(15)—C(25)—H(30)	110.36 (6)
O(11)—C(12)—H(5)	109.40 (6)	O(15)—C(25)—H(31)	110.75 (6)
C(11)—C(12)—H(4)	112.06 (6)	C(26)—C(25)—H(30)	108.88 (6)
C(11)—C(12)—H(5)	108.56 (6)	C(26)—C(25)—H(31)	110.03 (6)
H(4)—C(12)—H(5)	106.88 (6)	H(30)—C(25)—H(31)	107.46 (6)
O(11)—C(13)—C(14)	109.60 (6)	O(16)—C(26)—C(25)	109.48 (6)
O(11)—C(13)—H(6)	110.39 (6)	O(16)—C(26)—H(32)	109.75 (6)
O(11)—C(13)—H(7)	110.10 (6)	O(16)—C(26)—H(33)	110.17 (6)
C(14)—C(13)—H(6)	109.94 (6)	C(25)—C(26)—H(32)	110.68 (6)
C(14)—C(13)—H(7)	108.94 (5)	C(25)—C(26)—H(33)	108.39 (6)
H(6)—C(13)—H(7)	107.83 (6)	H(32)—C(26)—H(33)	108.34 (6)
O(12)—C(14)—C(13)	108.59 (6)	O(16)—C(27)—C(28)	110.48 (6)
O(12)—C(14)—H(8)	110.27 (6)	O(16)—C(27)—H(34)	109.62 (6)
O(12)—C(14)—H(9)	110.33 (7)	O(16)—C(27)—H(35)	108.98 (6)
C(13)—C(14)—H(8)	108.36 (6)	C(28)—C(27)—H(34)	111.87 (6)
C(13)—C(14)—H(9)	110.82 (6)	C(28)—C(27)—H(35)	108.61 (6)
H(8)—C(14)—H(9)	108.46 (5)	H(34)—C(27)—H(35)	107.18 (6)
O(12)—C(15)—C(16)	108.66 (6)	N(2)—C(28)—C(27)	114.08 (6)
O(12)—C(15)—H(10)	109.71 (7)	N(2)—C(28)—H(36)	111.31 (6)
O(12)—C(15)—H(11)	109.46 (6)	N(2)—C(28)—H(37)	107.92 (6)
C(16)—C(15)—H(10)	108.14 (6)	C(27)—C(28)—H(36)	108.19 (6)
C(16)—C(15)—H(11)	113.03 (6)	C(27)—C(28)—H(37)	108.41 (6)
H(10)—C(15)—H(11)	107.80 (5)	H(36)—C(28)—H(37)	106.63 (6)